data_jh1018b
_audit_creation_date               2018-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C16 H16 B N3 O3'
_chemical_formula_sum              'C16 H16 B N3 O3'
_chemical_formula_weight           309.13
_chemical_absolute_configuration   unk
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     5.95450(10)
_cell_length_b                     4.96270(10)
_cell_length_c                     25.4669(7)
_cell_angle_alpha                  90
_cell_angle_beta                   91.886(2)
_cell_angle_gamma                  90
_cell_volume                       752.15(3)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      3090
_cell_measurement_temperature      173(2)
_cell_measurement_theta_max        69.93
_cell_measurement_theta_min        5.21
_shelx_estimated_absorpt_T_max     0.983
_shelx_estimated_absorpt_T_min     0.845
_exptl_absorpt_coefficient_mu      0.777
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.6101
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.365
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         plate
_exptl_crystal_F_000               324
_exptl_crystal_recrystallization_method  'used as received'
_exptl_crystal_size_max            0.224
_exptl_crystal_size_mid            0.119
_exptl_crystal_size_min            0.022
_exptl_special_details            
 'Data was collected using a BRUKER CCD (charge coupled device) based diffractometer equipped with an Oxford low-temperature apparatus operating at 173 K. A suitable crystal was chosen and mounted on a nylon loop using Paratone oil. Data were measured using omega and phi scans of 1.0° per frame for 30 s. The total number of images were based on results from the program COSMO where redundancy was expected to be 4 and completeness to 0.83Α to 100. Cell parameters were retrieved using APEX II software and refined using SAINT on all observed reflections.Data reduction was performed using the SAINT software which corrects for Lp. Scaling and absorption corrections were applied using SADABS6 multi-scan technique, supplied by George Sheldrick. The structure was solved by the direct method using the SHELXT program and refined by least squares method on F2, SHELXL, incorporated in OLEX2.'
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0558
_diffrn_reflns_av_unetI/netI       0.0518
_diffrn_reflns_Laue_measured_fraction_full  0.990
_diffrn_reflns_Laue_measured_fraction_max  0.983
_diffrn_reflns_limit_h_max         7
_diffrn_reflns_limit_h_min         -6
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -6
_diffrn_reflns_limit_l_max         30
_diffrn_reflns_limit_l_min         -30
_diffrn_reflns_number              7362
_diffrn_reflns_point_group_measured_fraction_full  0.964
_diffrn_reflns_point_group_measured_fraction_max  0.954
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           70.003
_diffrn_reflns_theta_min           5.213
_diffrn_ambient_temperature        173(2)
_diffrn_detector_area_resol_mean   8.36
_diffrn_measured_fraction_theta_full  0.990
_diffrn_measured_fraction_theta_max  0.983
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'sealed tube'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.725
_reflns_Friedel_fraction_full      0.931
_reflns_Friedel_fraction_max       0.917
_reflns_number_gt                  2265
_reflns_number_total               2719
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.188
_refine_diff_density_min           -0.255
_refine_diff_density_rms           0.048
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack     0.2(4)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       225
_refine_ls_number_reflns           2719
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0569
_refine_ls_R_factor_gt             0.0433
_refine_ls_restrained_S_all        1.040
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0542P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0952
_refine_ls_wR_factor_ref           0.1021
_refine_special_details           
 'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8
 0.2
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C9(H9)
3.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.4810(4) 0.0380(5) 0.21791(10) 0.0246(5) Uani 1 1 d . . . . .
 H1 H 0.599(7) 0.045(9) 0.2118(15) 0.030(12) Uiso 1 1 d . . . . .
 O2 O -0.1292(3) 0.3463(5) 0.28741(9) 0.0282(6) Uani 1 1 d . . . . .
 O3 O 0.9569(4) 0.8718(6) 0.47787(10) 0.0335(6) Uani 1 1 d . . . . .
 H3 H 0.994(9) 0.735(11) 0.493(2) 0.055(15) Uiso 1 1 d . . . . .
 N1 N 0.1131(4) 0.2563(6) 0.22042(11) 0.0238(6) Uani 1 1 d . . . . .
 N2 N -0.0504(4) 0.1460(7) 0.18632(12) 0.0299(7) Uani 1 1 d . . . . .
 N3 N 0.4302(4) 0.4992(6) 0.25300(11) 0.0201(6) Uani 1 1 d . . . . .
 H3A H 0.569(6) 0.466(7) 0.2630(13) 0.019(9) Uiso 1 1 d . . . . .
 H3B H 0.421(5) 0.670(7) 0.2432(12) 0.009(8) Uiso 1 1 d . . . . .
 C1 C -0.0028(6) 0.1697(9) 0.13734(15) 0.0355(9) Uani 1 1 d . . . . .
 H1A H -0.102251 0.083314 0.112735 0.043 Uiso 1 1 calc R . . . .
 C2 C 0.1868(6) 0.3142(8) 0.11554(14) 0.0306(8) Uani 1 1 d . . . . .
 C3 C 0.3685(5) 0.3971(7) 0.14831(13) 0.0259(8) Uani 1 1 d . . . . .
 C4 C 0.5343(6) 0.5529(7) 0.12649(14) 0.0307(8) Uani 1 1 d . . . . .
 H4 H 0.659116 0.610007 0.147875 0.037 Uiso 1 1 calc R . . . .
 C5 C 0.5213(7) 0.6273(9) 0.07382(16) 0.0406(10) Uani 1 1 d . . . . .
 H5 H 0.636127 0.735806 0.059737 0.049 Uiso 1 1 calc R . . . .
 C6 C 0.3422(8) 0.5442(9) 0.04178(15) 0.0460(10) Uani 1 1 d . . . . .
 H6 H 0.334888 0.594971 0.005798 0.055 Uiso 1 1 calc R . . . .
 C7 C 0.1746(7) 0.3879(10) 0.06202(15) 0.0419(10) Uani 1 1 d . . . . .
 H7 H 0.051708 0.330232 0.040102 0.050 Uiso 1 1 calc R . . . .
 C8 C 0.0564(5) 0.3463(7) 0.26768(12) 0.0215(7) Uani 1 1 d . . . . .
 C9 C 0.2697(5) 0.4505(6) 0.29611(13) 0.0216(7) Uani 1 1 d . . . . .
 H9 H 0.331867 0.301063 0.318560 0.026 Uiso 1 1 calc R . . . .
 C10 C 0.2297(5) 0.6891(7) 0.33126(13) 0.0248(7) Uani 1 1 d . . . . .
 H10A H 0.090967 0.657904 0.350774 0.030 Uiso 1 1 calc R . . . .
 H10B H 0.206013 0.851685 0.309257 0.030 Uiso 1 1 calc R . . . .
 C11 C 0.4237(5) 0.7398(7) 0.37032(13) 0.0234(7) Uani 1 1 d . . . . .
 C12 C 0.4339(6) 0.6028(7) 0.41798(13) 0.0275(8) Uani 1 1 d . . . . .
 H12 H 0.317188 0.480550 0.426035 0.033 Uiso 1 1 calc R . . . .
 C13 C 0.6109(6) 0.6409(8) 0.45400(14) 0.0295(8) Uani 1 1 d . . . . .
 H13 H 0.616716 0.543187 0.486101 0.035 Uiso 1 1 calc R . . . .
 C14 C 0.7785(5) 0.8221(7) 0.44274(13) 0.0257(7) Uani 1 1 d . . . . .
 C15 C 0.7736(5) 0.9598(7) 0.39579(14) 0.0261(8) Uani 1 1 d . . . . .
 H15 H 0.889776 1.083684 0.388196 0.031 Uiso 1 1 calc R . . . .
 C16 C 0.5972(5) 0.9162(7) 0.35947(13) 0.0233(7) Uani 1 1 d . . . . .
 H16 H 0.595520 1.008624 0.326786 0.028 Uiso 1 1 calc R . . . .
 B1 B 0.3631(6) 0.2855(8) 0.20730(15) 0.0221(8) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 H1 0.73(4) . ?
 O1 B1 1.436(5) . ?
 O2 C8 1.229(4) . ?
 O3 H3 0.81(5) . ?
 O3 C14 1.388(4) . ?
 N1 N2 1.395(4) . ?
 N1 C8 1.337(4) . ?
 N1 B1 1.543(4) . ?
 N2 C1 1.294(5) . ?
 N3 H3A 0.87(4) . ?
 N3 H3B 0.89(4) . ?
 N3 C9 1.499(4) . ?
 N3 B1 1.615(5) . ?
 C1 H1A 0.9500 . ?
 C1 C2 1.462(5) . ?
 C2 C3 1.406(5) . ?
 C2 C7 1.411(5) . ?
 C3 C4 1.385(5) . ?
 C3 B1 1.602(5) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.391(5) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.384(6) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.377(6) . ?
 C7 H7 0.9500 . ?
 C8 C9 1.531(4) . ?
 C9 H9 1.0000 . ?
 C9 C10 1.508(5) . ?
 C10 H10A 0.9900 . ?
 C10 H10B 0.9900 . ?
 C10 C11 1.520(4) . ?
 C11 C12 1.391(5) . ?
 C11 C16 1.389(5) . ?
 C12 H12 0.9500 . ?
 C12 C13 1.387(5) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.381(5) . ?
 C14 C15 1.377(5) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.394(4) . ?
 C16 H16 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 B1 O1 H1 113(4) . . ?
 C14 O3 H3 111(4) . . ?
 N2 N1 B1 124.1(3) . . ?
 C8 N1 N2 120.0(3) . . ?
 C8 N1 B1 115.9(3) . . ?
 C1 N2 N1 113.2(3) . . ?
 H3A N3 H3B 108(3) . . ?
 C9 N3 H3A 112(2) . . ?
 C9 N3 H3B 109(2) . . ?
 C9 N3 B1 105.9(2) . . ?
 B1 N3 H3A 107(2) . . ?
 B1 N3 H3B 114(2) . . ?
 N2 C1 H1A 116.3 . . ?
 N2 C1 C2 127.4(3) . . ?
 C2 C1 H1A 116.3 . . ?
 C3 C2 C1 120.4(3) . . ?
 C3 C2 C7 120.8(4) . . ?
 C7 C2 C1 118.6(3) . . ?
 C2 C3 B1 114.6(3) . . ?
 C4 C3 C2 118.0(3) . . ?
 C4 C3 B1 127.3(3) . . ?
 C3 C4 H4 119.4 . . ?
 C3 C4 C5 121.1(4) . . ?
 C5 C4 H4 119.4 . . ?
 C4 C5 H5 119.8 . . ?
 C6 C5 C4 120.5(4) . . ?
 C6 C5 H5 119.8 . . ?
 C5 C6 H6 120.0 . . ?
 C7 C6 C5 120.1(4) . . ?
 C7 C6 H6 120.0 . . ?
 C2 C7 H7 120.2 . . ?
 C6 C7 C2 119.5(4) . . ?
 C6 C7 H7 120.2 . . ?
 O2 C8 N1 128.7(3) . . ?
 O2 C8 C9 123.4(3) . . ?
 N1 C8 C9 108.0(3) . . ?
 N3 C9 C8 104.3(3) . . ?
 N3 C9 H9 107.8 . . ?
 N3 C9 C10 115.2(3) . . ?
 C8 C9 H9 107.8 . . ?
 C10 C9 C8 113.6(3) . . ?
 C10 C9 H9 107.8 . . ?
 C9 C10 H10A 109.0 . . ?
 C9 C10 H10B 109.0 . . ?
 C9 C10 C11 112.8(3) . . ?
 H10A C10 H10B 107.8 . . ?
 C11 C10 H10A 109.0 . . ?
 C11 C10 H10B 109.0 . . ?
 C12 C11 C10 120.0(3) . . ?
 C16 C11 C10 121.9(3) . . ?
 C16 C11 C12 118.1(3) . . ?
 C11 C12 H12 119.3 . . ?
 C13 C12 C11 121.4(3) . . ?
 C13 C12 H12 119.3 . . ?
 C12 C13 H13 120.3 . . ?
 C14 C13 C12 119.3(3) . . ?
 C14 C13 H13 120.3 . . ?
 C13 C14 O3 121.7(3) . . ?
 C15 C14 O3 117.7(3) . . ?
 C15 C14 C13 120.6(3) . . ?
 C14 C15 H15 120.2 . . ?
 C14 C15 C16 119.6(3) . . ?
 C16 C15 H15 120.2 . . ?
 C11 C16 C15 121.0(3) . . ?
 C11 C16 H16 119.5 . . ?
 C15 C16 H16 119.5 . . ?
 O1 B1 N1 110.4(3) . . ?
 O1 B1 N3 108.5(3) . . ?
 O1 B1 C3 116.6(3) . . ?
 N1 B1 N3 97.1(3) . . ?
 N1 B1 C3 106.5(3) . . ?
 C3 B1 N3 115.9(3) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 O3 H3 O3 0.81(5) 1.96(5) 2.766(2) 170(5) 2_746 yes
 N3 H3A O2 0.87(4) 1.97(4) 2.841(3) 173(3) 1_655 yes
 N3 H3B O1 0.89(4) 1.97(4) 2.839(4) 166(3) 1_565 yes

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O2 C8 C9 N3 -161.5(3) . . . . ?
 O2 C8 C9 C10 -35.2(5) . . . . ?
 O3 C14 C15 C16 -179.9(3) . . . . ?
 N1 N2 C1 C2 -5.5(6) . . . . ?
 N1 C8 C9 N3 19.8(3) . . . . ?
 N1 C8 C9 C10 146.0(3) . . . . ?
 N2 N1 C8 O2 0.5(5) . . . . ?
 N2 N1 C8 C9 179.2(3) . . . . ?
 N2 N1 B1 O1 -83.6(4) . . . . ?
 N2 N1 B1 N3 163.6(3) . . . . ?
 N2 N1 B1 C3 43.8(4) . . . . ?
 N2 C1 C2 C3 14.0(6) . . . . ?
 N2 C1 C2 C7 -160.7(4) . . . . ?
 N3 C9 C10 C11 -76.0(4) . . . . ?
 C1 C2 C3 C4 -174.6(3) . . . . ?
 C1 C2 C3 B1 8.0(5) . . . . ?
 C1 C2 C7 C6 174.4(4) . . . . ?
 C2 C3 C4 C5 0.5(5) . . . . ?
 C2 C3 B1 O1 92.6(3) . . . . ?
 C2 C3 B1 N1 -31.1(4) . . . . ?
 C2 C3 B1 N3 -137.8(3) . . . . ?
 C3 C2 C7 C6 -0.3(6) . . . . ?
 C3 C4 C5 C6 -0.7(6) . . . . ?
 C4 C3 B1 O1 -84.5(4) . . . . ?
 C4 C3 B1 N1 151.9(3) . . . . ?
 C4 C3 B1 N3 45.2(4) . . . . ?
 C4 C5 C6 C7 0.3(7) . . . . ?
 C5 C6 C7 C2 0.2(6) . . . . ?
 C7 C2 C3 C4 0.0(5) . . . . ?
 C7 C2 C3 B1 -177.3(3) . . . . ?
 C8 N1 N2 C1 153.2(3) . . . . ?
 C8 N1 B1 O1 96.9(4) . . . . ?
 C8 N1 B1 N3 -16.0(4) . . . . ?
 C8 N1 B1 C3 -135.7(3) . . . . ?
 C8 C9 C10 C11 163.7(3) . . . . ?
 C9 N3 B1 O1 -87.3(3) . . . . ?
 C9 N3 B1 N1 27.0(3) . . . . ?
 C9 N3 B1 C3 139.3(3) . . . . ?
 C9 C10 C11 C12 -85.5(4) . . . . ?
 C9 C10 C11 C16 92.9(4) . . . . ?
 C10 C11 C12 C13 178.8(3) . . . . ?
 C10 C11 C16 C15 -179.9(3) . . . . ?
 C11 C12 C13 C14 1.2(5) . . . . ?
 C12 C11 C16 C15 -1.5(5) . . . . ?
 C12 C13 C14 O3 178.7(3) . . . . ?
 C12 C13 C14 C15 -1.5(5) . . . . ?
 C13 C14 C15 C16 0.3(5) . . . . ?
 C14 C15 C16 C11 1.3(5) . . . . ?
 C16 C11 C12 C13 0.3(5) . . . . ?
 B1 N1 N2 C1 -26.4(5) . . . . ?
 B1 N1 C8 O2 -180.0(3) . . . . ?
 B1 N1 C8 C9 -1.3(4) . . . . ?
 B1 N3 C9 C8 -29.4(3) . . . . ?
 B1 N3 C9 C10 -154.7(3) . . . . ?
 B1 C3 C4 C5 177.5(3) . . . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id  '2  Tyrosine hydrazide DAB'
_olex2_submission_special_instructions  'No special instructions were received'
loop_
  _twin_individual_id
  _twin_individual_mass_fraction_refined
 1 0.8
 2 0.2

#===END

data_jh1018c
_audit_creation_date               2018-11-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H20 B N3 O3'
_chemical_formula_sum              'C18 H20 B N3 O3'
_chemical_formula_weight           337.18
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                     9.36910(10)
_cell_length_b                     7.73170(10)
_cell_length_c                     23.2871(3)
_cell_angle_alpha                  90
_cell_angle_beta                   101.2600(10)
_cell_angle_gamma                  90
_cell_volume                       1654.42(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9900
_cell_measurement_temperature      173(2)
_cell_measurement_theta_max        68.21
_cell_measurement_theta_min        3.87
_shelx_estimated_absorpt_T_max     0.956
_shelx_estimated_absorpt_T_min     0.898
_exptl_absorpt_coefficient_mu      0.750
_exptl_absorpt_correction_T_max    0.7531
_exptl_absorpt_correction_T_min    0.6887
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0602 before and 0.0518 after correction. The Ratio of minimum to maximum transmission is 0.9145. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.354
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'block'
_exptl_crystal_F_000               712
_exptl_crystal_recrystallization_method  'used as received'
_exptl_crystal_size_max            0.147
_exptl_crystal_size_mid            0.09
_exptl_crystal_size_min            0.06
_exptl_special_details
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0392
_diffrn_reflns_av_unetI/netI       0.0192
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.999
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         9
_diffrn_reflns_limit_k_min         -9
_diffrn_reflns_limit_l_max         27
_diffrn_reflns_limit_l_min         -28
_diffrn_reflns_number              24576
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.999
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           68.236
_diffrn_reflns_theta_min           3.871
_diffrn_ambient_temperature        173(2)
_diffrn_detector_area_resol_mean   8.36
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.999
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'ω and φ'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'sealed tube'
_diffrn_special_details            ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2648
_reflns_number_total               3041
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement   
 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution     
 'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max           0.237
_refine_diff_density_min           -0.223
_refine_diff_density_rms           0.045
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.033
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       236
_refine_ls_number_reflns           3041
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0412
_refine_ls_R_factor_gt             0.0350
_refine_ls_restrained_S_all        1.033
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0524P)²+0.4552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0881
_refine_ls_wR_factor_ref           0.0932
_refine_special_details
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom(s) on the non-carbon atom(s) 
which was found by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C14(H14), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1 O 0.55886(9) 0.53253(11) 0.38157(4) 0.0218(2) Uani 1 1 d . . . . .
 H1 H 0.536(2) 0.602(3) 0.4067(8) 0.044(5) Uiso 1 1 d . . . . .
 O2 O 0.53035(10) 0.24669(11) 0.53830(4) 0.0255(2) Uani 1 1 d . . . . .
 O3 O 1.23618(10) 0.30658(13) 0.66761(4) 0.0295(2) Uani 1 1 d . . . . .
 H3 H 1.304(2) 0.364(3) 0.6523(8) 0.051(5) Uiso 1 1 d . . . . .
 N1 N 0.43624(11) 0.34599(13) 0.44446(5) 0.0191(2) Uani 1 1 d . . . . .
 N2 N 0.30295(11) 0.39789(14) 0.45696(5) 0.0232(2) Uani 1 1 d . . . . .
 N3 N 0.60960(11) 0.21628(13) 0.39557(5) 0.0202(2) Uani 1 1 d . . . . .
 C1 C 0.20261(14) 0.41454(17) 0.41101(6) 0.0253(3) Uani 1 1 d . . . . .
 H1A H 0.112587 0.460164 0.417090 0.030 Uiso 1 1 calc R . . . .
 C2 C 0.21025(14) 0.37175(17) 0.35048(6) 0.0245(3) Uani 1 1 d . . . . .
 C3 C 0.34502(14) 0.33758(16) 0.33445(6) 0.0215(3) Uani 1 1 d . . . . .
 C4 C 0.34237(16) 0.28856(18) 0.27662(6) 0.0285(3) Uani 1 1 d . . . . .
 H4 H 0.431754 0.267429 0.264379 0.034 Uiso 1 1 calc R . . . .
 C5 C 0.21274(18) 0.26976(19) 0.23642(6) 0.0357(4) Uani 1 1 d . . . . .
 H5 H 0.214267 0.233514 0.197562 0.043 Uiso 1 1 calc R . . . .
 C6 C 0.08132(17) 0.3037(2) 0.25286(7) 0.0380(4) Uani 1 1 d . . . . .
 H6 H -0.007475 0.290172 0.225486 0.046 Uiso 1 1 calc R . . . .
 C7 C 0.08009(15) 0.3574(2) 0.30927(7) 0.0333(3) Uani 1 1 d . . . . .
 H7 H -0.009713 0.384931 0.320256 0.040 Uiso 1 1 calc R . . . .
 C8 C 0.53731(14) 0.27710(15) 0.48708(5) 0.0200(3) Uani 1 1 d . . . . .
 C9 C 0.67059(13) 0.23635(15) 0.46064(5) 0.0206(3) Uani 1 1 d . . . . .
 H9 H 0.733341 0.342028 0.465498 0.025 Uiso 1 1 calc R . . . .
 C10 C 0.54318(14) 0.04159(16) 0.38266(6) 0.0248(3) Uani 1 1 d . . . . .
 H10A H 0.619228 -0.046950 0.391135 0.037 Uiso 1 1 calc GR . . . .
 H10B H 0.496038 0.035246 0.341269 0.037 Uiso 1 1 calc GR . . . .
 H10C H 0.470656 0.021807 0.407117 0.037 Uiso 1 1 calc GR . . . .
 C11 C 0.72621(15) 0.24050(18) 0.36094(6) 0.0286(3) Uani 1 1 d . . . . .
 H11A H 0.772171 0.353691 0.369997 0.043 Uiso 1 1 calc GR . . . .
 H11B H 0.683630 0.234430 0.319061 0.043 Uiso 1 1 calc GR . . . .
 H11C H 0.799460 0.149293 0.370995 0.043 Uiso 1 1 calc GR . . . .
 C12 C 0.76419(14) 0.08658(16) 0.49018(6) 0.0256(3) Uani 1 1 d . . . . .
 H12A H 0.701802 0.005002 0.506901 0.031 Uiso 1 1 calc R . . . .
 H12B H 0.806017 0.023466 0.460360 0.031 Uiso 1 1 calc R . . . .
 C13 C 0.88642(13) 0.14800(16) 0.53830(6) 0.0225(3) Uani 1 1 d . . . . .
 C14 C 0.89625(14) 0.10359(18) 0.59670(6) 0.0269(3) Uani 1 1 d . . . . .
 H14 H 0.821704 0.035252 0.607703 0.032 Uiso 1 1 calc R . . . .
 C15 C 1.01307(15) 0.15716(19) 0.63941(6) 0.0279(3) Uani 1 1 d . . . . .
 H15 H 1.017866 0.124889 0.679103 0.034 Uiso 1 1 calc R . . . .
 C16 C 1.12293(14) 0.25790(16) 0.62415(6) 0.0227(3) Uani 1 1 d . . . . .
 C17 C 1.11534(14) 0.30267(16) 0.56585(6) 0.0226(3) Uani 1 1 d . . . . .
 H17 H 1.190089 0.370553 0.554798 0.027 Uiso 1 1 calc R . . . .
 C18 C 0.99794(14) 0.24767(16) 0.52382(6) 0.0233(3) Uani 1 1 d . . . . .
 H18 H 0.993630 0.278947 0.484065 0.028 Uiso 1 1 calc R . . . .
 B1 B 0.48377(15) 0.37014(18) 0.38517(6) 0.0193(3) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1 H1 0.85(2) . ?
 O1 B1 1.4497(16) . ?
 O2 C8 1.2299(15) . ?
 O3 H3 0.90(2) . ?
 O3 C16 1.3683(16) . ?
 N1 N2 1.3955(14) . ?
 N1 C8 1.3410(16) . ?
 N1 B1 1.5425(17) . ?
 N2 C1 1.2855(17) . ?
 N3 C9 1.5196(16) . ?
 N3 C10 1.4929(16) . ?
 N3 C11 1.4909(16) . ?
 N3 B1 1.6589(16) . ?
 C1 H1A 0.9500 . ?
 C1 C2 1.4632(19) . ?
 C2 C3 1.4098(19) . ?
 C2 C7 1.4012(19) . ?
 C3 C4 1.3946(19) . ?
 C3 B1 1.5965(18) . ?
 C4 H4 0.9500 . ?
 C4 C5 1.389(2) . ?
 C5 H5 0.9500 . ?
 C5 C6 1.384(2) . ?
 C6 H6 0.9500 . ?
 C6 C7 1.380(2) . ?
 C7 H7 0.9500 . ?
 C8 C9 1.5289(17) . ?
 C9 H9 1.0000 . ?
 C9 C12 1.5321(17) . ?
 C10 H10A 0.9800 . ?
 C10 H10B 0.9800 . ?
 C10 H10C 0.9800 . ?
 C11 H11A 0.9800 . ?
 C11 H11B 0.9800 . ?
 C11 H11C 0.9800 . ?
 C12 H12A 0.9900 . ?
 C12 H12B 0.9900 . ?
 C12 C13 1.5138(17) . ?
 C13 C14 1.3881(19) . ?
 C13 C18 1.3918(19) . ?
 C14 H14 0.9500 . ?
 C14 C15 1.3905(19) . ?
 C15 H15 0.9500 . ?
 C15 C16 1.3911(19) . ?
 C16 C17 1.3894(18) . ?
 C17 H17 0.9500 . ?
 C17 C18 1.3887(18) . ?
 C18 H18 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 B1 O1 H1 108.5(13) . . ?
 C16 O3 H3 110.3(12) . . ?
 N2 N1 B1 125.34(10) . . ?
 C8 N1 N2 119.42(11) . . ?
 C8 N1 B1 115.15(10) . . ?
 C1 N2 N1 113.19(11) . . ?
 C9 N3 B1 100.98(9) . . ?
 C10 N3 C9 110.73(10) . . ?
 C10 N3 B1 111.28(9) . . ?
 C11 N3 C9 110.73(10) . . ?
 C11 N3 C10 108.99(10) . . ?
 C11 N3 B1 113.95(10) . . ?
 N2 C1 H1A 116.1 . . ?
 N2 C1 C2 127.87(12) . . ?
 C2 C1 H1A 116.1 . . ?
 C3 C2 C1 120.82(11) . . ?
 C7 C2 C1 118.54(12) . . ?
 C7 C2 C3 120.57(13) . . ?
 C2 C3 B1 114.62(11) . . ?
 C4 C3 C2 117.30(12) . . ?
 C4 C3 B1 128.01(12) . . ?
 C3 C4 H4 119.1 . . ?
 C5 C4 C3 121.86(14) . . ?
 C5 C4 H4 119.1 . . ?
 C4 C5 H5 119.9 . . ?
 C6 C5 C4 120.11(14) . . ?
 C6 C5 H5 119.9 . . ?
 C5 C6 H6 120.2 . . ?
 C7 C6 C5 119.59(13) . . ?
 C7 C6 H6 120.2 . . ?
 C2 C7 H7 119.7 . . ?
 C6 C7 C2 120.51(14) . . ?
 C6 C7 H7 119.7 . . ?
 O2 C8 N1 129.06(12) . . ?
 O2 C8 C9 123.59(11) . . ?
 N1 C8 C9 107.34(10) . . ?
 N3 C9 C8 104.18(9) . . ?
 N3 C9 H9 107.1 . . ?
 N3 C9 C12 116.19(10) . . ?
 C8 C9 H9 107.1 . . ?
 C8 C9 C12 114.58(11) . . ?
 C12 C9 H9 107.1 . . ?
 N3 C10 H10A 109.5 . . ?
 N3 C10 H10B 109.5 . . ?
 N3 C10 H10C 109.5 . . ?
 H10A C10 H10B 109.5 . . ?
 H10A C10 H10C 109.5 . . ?
 H10B C10 H10C 109.5 . . ?
 N3 C11 H11A 109.5 . . ?
 N3 C11 H11B 109.5 . . ?
 N3 C11 H11C 109.5 . . ?
 H11A C11 H11B 109.5 . . ?
 H11A C11 H11C 109.5 . . ?
 H11B C11 H11C 109.5 . . ?
 C9 C12 H12A 109.1 . . ?
 C9 C12 H12B 109.1 . . ?
 H12A C12 H12B 107.9 . . ?
 C13 C12 C9 112.28(10) . . ?
 C13 C12 H12A 109.1 . . ?
 C13 C12 H12B 109.1 . . ?
 C14 C13 C12 122.93(12) . . ?
 C14 C13 C18 117.71(12) . . ?
 C18 C13 C12 119.31(12) . . ?
 C13 C14 H14 119.4 . . ?
 C13 C14 C15 121.29(12) . . ?
 C15 C14 H14 119.4 . . ?
 C14 C15 H15 119.9 . . ?
 C14 C15 C16 120.16(13) . . ?
 C16 C15 H15 119.9 . . ?
 O3 C16 C15 118.08(12) . . ?
 O3 C16 C17 122.58(12) . . ?
 C17 C16 C15 119.33(12) . . ?
 C16 C17 H17 120.2 . . ?
 C18 C17 C16 119.66(12) . . ?
 C18 C17 H17 120.2 . . ?
 C13 C18 H18 119.1 . . ?
 C17 C18 C13 121.84(12) . . ?
 C17 C18 H18 119.1 . . ?
 O1 B1 N1 112.63(10) . . ?
 O1 B1 N3 106.88(10) . . ?
 O1 B1 C3 115.34(11) . . ?
 N1 B1 N3 95.95(9) . . ?
 N1 B1 C3 107.91(10) . . ?
 C3 B1 N3 116.60(10) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 O1 H1 O2 0.85(2) 1.93(2) 2.7755(13) 175.4(18) 3_666 yes

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O2 C8 C9 N3 154.89(11) . . . . ?
 O2 C8 C9 C12 26.87(17) . . . . ?
 O3 C16 C17 C18 179.41(11) . . . . ?
 N1 N2 C1 C2 5.74(19) . . . . ?
 N1 C8 C9 N3 -24.19(12) . . . . ?
 N1 C8 C9 C12 -152.21(10) . . . . ?
 N2 N1 C8 O2 1.89(19) . . . . ?
 N2 N1 C8 C9 -179.10(10) . . . . ?
 N2 N1 B1 O1 90.35(14) . . . . ?
 N2 N1 B1 N3 -158.56(10) . . . . ?
 N2 N1 B1 C3 -38.11(15) . . . . ?
 N2 C1 C2 C3 -13.2(2) . . . . ?
 N2 C1 C2 C7 163.84(14) . . . . ?
 N3 C9 C12 C13 145.68(11) . . . . ?
 C1 C2 C3 C4 176.58(12) . . . . ?
 C1 C2 C3 B1 -6.43(17) . . . . ?
 C1 C2 C7 C6 -174.74(13) . . . . ?
 C2 C3 C4 C5 -1.49(19) . . . . ?
 C2 C3 B1 O1 -100.14(13) . . . . ?
 C2 C3 B1 N1 26.76(14) . . . . ?
 C2 C3 B1 N3 133.25(11) . . . . ?
 C3 C2 C7 C6 2.3(2) . . . . ?
 C3 C4 C5 C6 1.5(2) . . . . ?
 C4 C3 B1 O1 76.47(16) . . . . ?
 C4 C3 B1 N1 -156.63(12) . . . . ?
 C4 C3 B1 N3 -50.15(17) . . . . ?
 C4 C5 C6 C7 0.4(2) . . . . ?
 C5 C6 C7 C2 -2.3(2) . . . . ?
 C7 C2 C3 C4 -0.40(19) . . . . ?
 C7 C2 C3 B1 176.59(12) . . . . ?
 C8 N1 N2 C1 -161.28(11) . . . . ?
 C8 N1 B1 O1 -86.07(13) . . . . ?
 C8 N1 B1 N3 25.02(12) . . . . ?
 C8 N1 B1 C3 145.46(10) . . . . ?
 C8 C9 C12 C13 -92.65(13) . . . . ?
 C9 N3 B1 O1 79.06(11) . . . . ?
 C9 N3 B1 N1 -36.79(10) . . . . ?
 C9 N3 B1 C3 -150.24(11) . . . . ?
 C9 C12 C13 C14 116.23(14) . . . . ?
 C9 C12 C13 C18 -66.49(15) . . . . ?
 C10 N3 C9 C8 -79.81(11) . . . . ?
 C10 N3 C9 C12 47.22(14) . . . . ?
 C10 N3 B1 O1 -163.40(10) . . . . ?
 C10 N3 B1 N1 80.76(11) . . . . ?
 C10 N3 B1 C3 -32.69(14) . . . . ?
 C11 N3 C9 C8 159.17(10) . . . . ?
 C11 N3 C9 C12 -73.80(13) . . . . ?
 C11 N3 B1 O1 -39.67(14) . . . . ?
 C11 N3 B1 N1 -155.52(10) . . . . ?
 C11 N3 B1 C3 91.03(13) . . . . ?
 C12 C13 C14 C15 177.56(12) . . . . ?
 C12 C13 C18 C17 -177.78(11) . . . . ?
 C13 C14 C15 C16 0.3(2) . . . . ?
 C14 C13 C18 C17 -0.36(19) . . . . ?
 C14 C15 C16 O3 -179.57(12) . . . . ?
 C14 C15 C16 C17 -0.7(2) . . . . ?
 C15 C16 C17 C18 0.55(19) . . . . ?
 C16 C17 C18 C13 -0.04(19) . . . . ?
 C18 C13 C14 C15 0.2(2) . . . . ?
 B1 N1 N2 C1 22.43(17) . . . . ?
 B1 N1 C8 O2 178.54(12) . . . . ?
 B1 N1 C8 C9 -2.45(14) . . . . ?
 B1 N3 C9 C8 38.13(11) . . . . ?
 B1 N3 C9 C12 165.16(10) . . . . ?
 B1 C3 C4 C5 -178.01(13) . . . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id  '3  Dimethyl Tyrosine hydrazide DAB'
_olex2_submission_special_instructions  'No special instructions were received'

#===END

data_jh1218a
_audit_creation_date               2018-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H16 B N3 O4'
_chemical_formula_sum              'C18 H16 B N3 O4'
_chemical_formula_weight           349.15
_chemical_absolute_configuration   ad
_chemical_melting_point            ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'B' 'B' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             4
_space_group_name_H-M_alt          'P 1 21 1'
_space_group_name_Hall             'P 2yb'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'

_cell_length_a                     11.20330(10)
_cell_length_b                     8.90940(10)
_cell_length_c                     16.9484(2)
_cell_angle_alpha                  90
_cell_angle_beta                   92.8770(10)
_cell_angle_gamma                  90
_cell_volume                       1689.57(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9967
_cell_measurement_temperature      173(2)
_cell_measurement_theta_max        70.04
_cell_measurement_theta_min        2.61
_shelx_estimated_absorpt_T_max     0.968
_shelx_estimated_absorpt_T_min     0.688
_exptl_absorpt_coefficient_mu      0.806
_exptl_absorpt_correction_T_max    0.7533
_exptl_absorpt_correction_T_min    0.6686
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0642 before and 0.0499 after correction. The Ratio of minimum to maximum transmission is 0.8876. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.373
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'needle'
_exptl_crystal_F_000               728
_exptl_crystal_recrystallization_method  'Used as received'
_exptl_crystal_size_max            0.502
_exptl_crystal_size_mid            0.224
_exptl_crystal_size_min            0.04
_exptl_special_details
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structure was solved 
by the direct method using the SHELXT program and refined by least squares 
method on F2, SHELXL, incorporated in OLEX2. 
;
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0267
_diffrn_reflns_av_unetI/netI       0.0281
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         13
_diffrn_reflns_limit_h_min         -13
_diffrn_reflns_limit_k_max         10
_diffrn_reflns_limit_k_min         -10
_diffrn_reflns_limit_l_max         20
_diffrn_reflns_limit_l_min         -20
_diffrn_reflns_number              18758
_diffrn_reflns_point_group_measured_fraction_full  0.985
_diffrn_reflns_point_group_measured_fraction_max  0.981
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           70.068
_diffrn_reflns_theta_min           2.610
_diffrn_ambient_temperature        173(2)
_diffrn_detector_area_resol_mean   8.36
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'ω and φ'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     'sealed tube'
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.842
_reflns_Friedel_fraction_full      0.972
_reflns_Friedel_fraction_max       0.963
_reflns_number_gt                  5751
_reflns_number_total               6315
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection         'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction          'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement   
 'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution     
 'SHELXT (Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8)'
_refine_diff_density_max           0.852
_refine_diff_density_min           -0.296
_refine_diff_density_rms           0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 2375 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.05(9)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       477
_refine_ls_number_reflns           6315
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0611
_refine_ls_R_factor_gt             0.0559
_refine_ls_restrained_S_all        1.037
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.1011P)²+0.7355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1581
_refine_ls_wR_factor_ref           0.1656
_refine_special_details
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the 
riding model, except for the hydrogen atom(s) on the non-carbon atom(s) 
which was found by difference Fourier methods and refined isotropically.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2B(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C12A(H12A,H12B), C3B(H3BA,H3BB), C12B(H12C,H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C7A(H7A), C8A(H8A), C9A(H9A), C10A(H10A), C14A(H14A), C15A(H15A),
 C16A(H16A), C17A(H17A), C18A(H18A), C4B(H4B), C7B(H7B), C8B(H8B), C9B(H9B),
 C10B(H10B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
loop_
  _atom_site_label
  _atom_site_type_symbol
  _atom_site_fract_x
  _atom_site_fract_y
  _atom_site_fract_z
  _atom_site_U_iso_or_equiv
  _atom_site_adp_type
  _atom_site_occupancy
  _atom_site_site_symmetry_order
  _atom_site_calc_flag
  _atom_site_refinement_flags_posn
  _atom_site_refinement_flags_adp
  _atom_site_refinement_flags_occupancy
  _atom_site_disorder_assembly
  _atom_site_disorder_group
 O1A O 0.4945(3) 0.3527(4) 0.4994(2) 0.0467(8) Uani 1 1 d . . . . .
 O2A O 0.3519(2) 0.1411(3) 0.30247(17) 0.0386(7) Uani 1 1 d . . . . .
 O3A O 0.8378(2) 0.1201(4) 0.41828(18) 0.0410(7) Uani 1 1 d . . . . .
 O4A O 0.7450(3) 0.2473(5) 0.3175(2) 0.0601(10) Uani 1 1 d . . . . .
 N1A N 0.3470(3) 0.3425(4) 0.4008(2) 0.0321(7) Uani 1 1 d . . . . .
 N2A N 0.2899(3) 0.4609(4) 0.4368(2) 0.0356(7) Uani 1 1 d . . . . .
 N3A N 0.6410(3) 0.1540(4) 0.4173(2) 0.0344(7) Uani 1 1 d . . . . .
 H3A H 0.646(4) 0.098(7) 0.456(3) 0.049(15) Uiso 1 1 d . . . . .
 C1A C 0.4586(3) 0.3059(5) 0.4364(2) 0.0333(8) Uani 1 1 d . . . . .
 C2A C 0.5300(3) 0.2074(4) 0.3822(2) 0.0323(8) Uani 1 1 d . . . . .
 H2A H 0.551249 0.272976 0.337158 0.039 Uiso 1 1 calc R . . . .
 C3A C 0.4536(4) 0.0803(5) 0.3460(3) 0.0385(9) Uani 1 1 d . . . . .
 H3AA H 0.501819 0.019621 0.310476 0.046 Uiso 1 1 calc R . . . .
 H3AB H 0.426611 0.013833 0.388465 0.046 Uiso 1 1 calc R . . . .
 C4A C 0.1916(4) 0.5077(5) 0.4030(3) 0.0376(9) Uani 1 1 d . . . . .
 H4A H 0.152674 0.587590 0.428562 0.045 Uiso 1 1 calc R . . . .
 C5A C 0.1327(4) 0.4521(5) 0.3299(2) 0.0354(9) Uani 1 1 d . . . . .
 C6A C 0.1828(3) 0.3309(5) 0.2914(2) 0.0339(8) Uani 1 1 d . . . . .
 C7A C 0.1261(4) 0.2773(5) 0.2212(3) 0.0396(9) Uani 1 1 d . . . . .
 H7A H 0.158741 0.194359 0.194522 0.048 Uiso 1 1 calc R . . . .
 C8A C 0.0225(4) 0.3454(6) 0.1909(3) 0.0463(11) Uani 1 1 d . . . . .
 H8A H -0.014449 0.309927 0.142801 0.056 Uiso 1 1 calc R . . . .
 C9A C -0.0276(4) 0.4636(6) 0.2297(3) 0.0493(12) Uani 1 1 d . . . . .
 H9A H -0.099545 0.507795 0.208787 0.059 Uiso 1 1 calc R . . . .
 C10A C 0.0268(4) 0.5185(5) 0.2992(3) 0.0435(10) Uani 1 1 d . . . . .
 H10A H -0.007492 0.600491 0.325854 0.052 Uiso 1 1 calc R . . . .
 C11A C 0.7406(4) 0.1786(5) 0.3790(2) 0.0377(9) Uani 1 1 d . . . . .
 C12A C 0.9469(4) 0.1426(10) 0.3787(4) 0.086(3) Uani 1 1 d . . . . .
 H12A H 0.952152 0.248117 0.360934 0.103 Uiso 1 1 calc R . . . .
 H12B H 0.948158 0.076801 0.331699 0.103 Uiso 1 1 calc R . . . .
 C13A C 1.0516(4) 0.1063(7) 0.4349(3) 0.0522(13) Uani 1 1 d . . . . .
 C14A C 1.0817(5) 0.2007(7) 0.4980(4) 0.0643(16) Uani 1 1 d . . . . .
 H14A H 1.035151 0.287567 0.507010 0.077 Uiso 1 1 calc R . . . .
 C15A C 1.1806(5) 0.1674(7) 0.5478(3) 0.0629(14) Uani 1 1 d . . . . .
 H15A H 1.201823 0.231634 0.591011 0.075 Uiso 1 1 calc R . . . .
 C16A C 1.2482(4) 0.0403(6) 0.5345(3) 0.0485(11) Uani 1 1 d . . . . .
 H16A H 1.314696 0.016153 0.569142 0.058 Uiso 1 1 calc R . . . .
 C17A C 1.2187(4) -0.0493(6) 0.4717(3) 0.0458(11) Uani 1 1 d . . . . .
 H17A H 1.265972 -0.135270 0.462008 0.055 Uiso 1 1 calc R . . . .
 C18A C 1.1209(4) -0.0169(6) 0.4219(3) 0.0457(11) Uani 1 1 d . . . . .
 H18A H 1.101463 -0.080660 0.378166 0.055 Uiso 1 1 calc R . . . .
 B1A B 0.2974(4) 0.2646(5) 0.3309(3) 0.0336(9) Uani 1 1 d . . . . .
 O1B O -0.0048(3) 0.6708(4) 0.01360(18) 0.0470(7) Uani 1 1 d . . . . .
 O2B O 0.1395(3) 0.8561(3) 0.21934(18) 0.0403(7) Uani 1 1 d . . . . .
 O3B O -0.3217(3) 0.8865(4) 0.0769(2) 0.0489(8) Uani 1 1 d . . . . .
 O4B O -0.2083(3) 0.7332(4) 0.1564(2) 0.0515(8) Uani 1 1 d . . . . .
 N1B N 0.1473(3) 0.6793(4) 0.10941(19) 0.0338(7) Uani 1 1 d . . . . .
 N2B N 0.2016(3) 0.5608(4) 0.0703(2) 0.0381(8) Uani 1 1 d . . . . .
 N3B N -0.1244(3) 0.9121(4) 0.0811(2) 0.0409(8) Uani 1 1 d . . . . .
 H3B H -0.135(4) 0.962(6) 0.047(3) 0.031(12) Uiso 1 1 d . . . . .
 C1B C 0.0422(4) 0.7307(5) 0.0711(2) 0.0344(8) Uani 1 1 d . . . . .
 C2B C -0.0013(4) 0.8791(5) 0.1043(2) 0.0370(9) Uani 1 1 d . . . . .
 H2B H 0.047958 0.959701 0.080857 0.044 Uiso 1 1 calc R . . . .
 C3B C 0.0194(4) 0.8918(5) 0.1942(3) 0.0413(10) Uani 1 1 d . . . . .
 H3BA H 0.001011 0.995381 0.210852 0.050 Uiso 1 1 calc R . . . .
 H3BB H -0.035775 0.822881 0.220137 0.050 Uiso 1 1 calc R . . . .
 C4B C 0.3008(4) 0.5098(5) 0.1013(2) 0.0388(9) Uani 1 1 d . . . . .
 H4B H 0.336342 0.429523 0.074006 0.047 Uiso 1 1 calc R . . . .
 C5B C 0.3644(4) 0.5600(5) 0.1727(2) 0.0353(8) Uani 1 1 d . . . . .
 C6B C 0.3158(3) 0.6777(5) 0.2158(2) 0.0345(8) Uani 1 1 d . . . . .
 C7B C 0.3756(4) 0.7254(5) 0.2852(2) 0.0395(9) Uani 1 1 d . . . . .
 H7B H 0.341596 0.801898 0.316005 0.047 Uiso 1 1 calc R . . . .
 C8B C 0.4840(4) 0.6627(5) 0.3098(3) 0.0443(10) Uani 1 1 d . . . . .
 H8B H 0.524678 0.697419 0.356842 0.053 Uiso 1 1 calc R . . . .
 C9B C 0.5338(4) 0.5483(5) 0.2656(3) 0.0434(10) Uani 1 1 d . . . . .
 H9B H 0.609089 0.506785 0.282185 0.052 Uiso 1 1 calc R . . . .
 C10B C 0.4740(4) 0.4952(5) 0.1979(3) 0.0409(9) Uani 1 1 d . . . . .
 H10B H 0.506886 0.415564 0.168697 0.049 Uiso 1 1 calc R . . . .
 C11B C -0.2166(4) 0.8339(5) 0.1089(3) 0.0406(9) Uani 1 1 d . . . . .
 C12B C -0.4258(4) 0.8115(8) 0.1066(4) 0.0656(17) Uani 1 1 d . . . . .
 H12C H -0.427419 0.825297 0.164538 0.079 Uiso 1 1 calc R . . . .
 H12D H -0.422146 0.702629 0.095415 0.079 Uiso 1 1 calc R . . . .
 C13B C -0.5352(4) 0.8774(6) 0.0671(3) 0.0554(14) Uani 1 1 d . . . . .
 C14B C -0.5825(5) 0.8061(11) -0.0001(4) 0.082(2) Uani 1 1 d . . . . .
 H14B H -0.538770 0.722156 -0.017722 0.099 Uiso 1 1 calc R . . . .
 C15B C -0.6833(6) 0.8408(11) -0.0440(5) 0.086(2) Uani 1 1 d . . . . .
 H15B H -0.710803 0.782638 -0.088190 0.103 Uiso 1 1 calc R . . . .
 C16B C -0.7410(7) 0.9622(8) -0.0206(5) 0.080(2) Uani 1 1 d . . . . .
 H16B H -0.810733 0.991277 -0.050997 0.096 Uiso 1 1 calc R . . . .
 C17B C -0.7076(4) 1.0492(7) 0.0441(4) 0.0620(15) Uani 1 1 d . . . . .
 H17B H -0.750781 1.136601 0.057553 0.074 Uiso 1 1 calc R . . . .
 C18B C -0.5999(6) 0.9978(8) 0.0916(5) 0.085(2) Uani 1 1 d . . . . .
 H18B H -0.575959 1.048698 0.139038 0.102 Uiso 1 1 calc R . . . .
 B1B B 0.1971(4) 0.7440(5) 0.1826(3) 0.0347(9) Uani 1 1 d . . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
  _geom_bond_atom_site_label_1
  _geom_bond_atom_site_label_2
  _geom_bond_distance
  _geom_bond_site_symmetry_2
  _geom_bond_publ_flag
 O1A C1A 1.197(5) . ?
 O2A C3A 1.433(5) . ?
 O2A B1A 1.359(6) . ?
 O3A C11A 1.352(5) . ?
 O3A C12A 1.437(5) . ?
 O4A C11A 1.213(5) . ?
 N1A N2A 1.391(5) . ?
 N1A C1A 1.400(5) . ?
 N1A B1A 1.458(6) . ?
 N2A C4A 1.285(5) . ?
 N3A H3A 0.83(6) . ?
 N3A C2A 1.432(5) . ?
 N3A C11A 1.336(5) . ?
 C1A C2A 1.525(6) . ?
 C2A H2A 1.0000 . ?
 C2A C3A 1.530(5) . ?
 C3A H3AA 0.9900 . ?
 C3A H3AB 0.9900 . ?
 C4A H4A 0.9500 . ?
 C4A C5A 1.462(6) . ?
 C5A C6A 1.394(6) . ?
 C5A C10A 1.402(6) . ?
 C6A C7A 1.404(6) . ?
 C6A B1A 1.536(6) . ?
 C7A H7A 0.9500 . ?
 C7A C8A 1.385(6) . ?
 C8A H8A 0.9500 . ?
 C8A C9A 1.375(8) . ?
 C9A H9A 0.9500 . ?
 C9A C10A 1.388(7) . ?
 C10A H10A 0.9500 . ?
 C12A H12A 0.9900 . ?
 C12A H12B 0.9900 . ?
 C12A C13A 1.509(7) . ?
 C13A C14A 1.388(9) . ?
 C13A C18A 1.369(7) . ?
 C14A H14A 0.9500 . ?
 C14A C15A 1.391(8) . ?
 C15A H15A 0.9500 . ?
 C15A C16A 1.386(8) . ?
 C16A H16A 0.9500 . ?
 C16A C17A 1.358(7) . ?
 C17A H17A 0.9500 . ?
 C17A C18A 1.381(6) . ?
 C18A H18A 0.9500 . ?
 O1B C1B 1.209(5) . ?
 O2B C3B 1.427(5) . ?
 O2B B1B 1.357(6) . ?
 O3B C11B 1.355(5) . ?
 O3B C12B 1.456(6) . ?
 O4B C11B 1.206(5) . ?
 N1B N2B 1.402(5) . ?
 N1B C1B 1.394(5) . ?
 N1B B1B 1.453(5) . ?
 N2B C4B 1.288(6) . ?
 N3B H3B 0.74(5) . ?
 N3B C2B 1.446(5) . ?
 N3B C11B 1.350(6) . ?
 C1B C2B 1.526(6) . ?
 C2B H2B 1.0000 . ?
 C2B C3B 1.533(6) . ?
 C3B H3BA 0.9900 . ?
 C3B H3BB 0.9900 . ?
 C4B H4B 0.9500 . ?
 C4B C5B 1.444(6) . ?
 C5B C6B 1.403(6) . ?
 C5B C10B 1.405(6) . ?
 C6B C7B 1.391(6) . ?
 C6B B1B 1.536(6) . ?
 C7B H7B 0.9500 . ?
 C7B C8B 1.382(6) . ?
 C8B H8B 0.9500 . ?
 C8B C9B 1.398(7) . ?
 C9B H9B 0.9500 . ?
 C9B C10B 1.383(6) . ?
 C10B H10B 0.9500 . ?
 C12B H12C 0.9900 . ?
 C12B H12D 0.9900 . ?
 C12B C13B 1.487(7) . ?
 C13B C14B 1.388(10) . ?
 C13B C18B 1.371(9) . ?
 C14B H14B 0.9500 . ?
 C14B C15B 1.356(9) . ?
 C15B H15B 0.9500 . ?
 C15B C16B 1.329(11) . ?
 C16B H16B 0.9500 . ?
 C16B C17B 1.380(10) . ?
 C17B H17B 0.9500 . ?
 C17B C18B 1.489(9) . ?
 C18B H18B 0.9500 . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 B1A O2A C3A 118.9(3) . . ?
 C11A O3A C12A 113.6(3) . . ?
 N2A N1A C1A 114.1(3) . . ?
 N2A N1A B1A 123.5(3) . . ?
 C1A N1A B1A 122.4(3) . . ?
 C4A N2A N1A 117.0(3) . . ?
 C2A N3A H3A 124(4) . . ?
 C11A N3A H3A 117(4) . . ?
 C11A N3A C2A 118.2(3) . . ?
 O1A C1A N1A 123.8(4) . . ?
 O1A C1A C2A 125.1(4) . . ?
 N1A C1A C2A 111.0(3) . . ?
 N3A C2A C1A 114.3(3) . . ?
 N3A C2A H2A 106.0 . . ?
 N3A C2A C3A 112.2(3) . . ?
 C1A C2A H2A 106.0 . . ?
 C1A C2A C3A 111.6(3) . . ?
 C3A C2A H2A 106.0 . . ?
 O2A C3A C2A 110.0(3) . . ?
 O2A C3A H3AA 109.7 . . ?
 O2A C3A H3AB 109.7 . . ?
 C2A C3A H3AA 109.7 . . ?
 C2A C3A H3AB 109.7 . . ?
 H3AA C3A H3AB 108.2 . . ?
 N2A C4A H4A 116.3 . . ?
 N2A C4A C5A 127.4(4) . . ?
 C5A C4A H4A 116.3 . . ?
 C6A C5A C4A 119.0(4) . . ?
 C6A C5A C10A 120.5(4) . . ?
 C10A C5A C4A 120.6(4) . . ?
 C5A C6A C7A 118.9(4) . . ?
 C5A C6A B1A 116.2(4) . . ?
 C7A C6A B1A 124.9(4) . . ?
 C6A C7A H7A 120.0 . . ?
 C8A C7A C6A 120.1(4) . . ?
 C8A C7A H7A 120.0 . . ?
 C7A C8A H8A 119.6 . . ?
 C9A C8A C7A 120.8(4) . . ?
 C9A C8A H8A 119.6 . . ?
 C8A C9A H9A 119.9 . . ?
 C8A C9A C10A 120.2(4) . . ?
 C10A C9A H9A 119.9 . . ?
 C5A C10A H10A 120.2 . . ?
 C9A C10A C5A 119.5(5) . . ?
 C9A C10A H10A 120.2 . . ?
 O4A C11A O3A 123.4(4) . . ?
 O4A C11A N3A 124.9(4) . . ?
 N3A C11A O3A 111.7(3) . . ?
 O3A C12A H12A 109.8 . . ?
 O3A C12A H12B 109.8 . . ?
 O3A C12A C13A 109.2(4) . . ?
 H12A C12A H12B 108.3 . . ?
 C13A C12A H12A 109.8 . . ?
 C13A C12A H12B 109.8 . . ?
 C14A C13A C12A 120.5(6) . . ?
 C18A C13A C12A 119.9(6) . . ?
 C18A C13A C14A 119.5(5) . . ?
 C13A C14A H14A 120.2 . . ?
 C13A C14A C15A 119.6(5) . . ?
 C15A C14A H14A 120.2 . . ?
 C14A C15A H15A 120.0 . . ?
 C16A C15A C14A 120.0(5) . . ?
 C16A C15A H15A 120.0 . . ?
 C15A C16A H16A 120.2 . . ?
 C17A C16A C15A 119.6(5) . . ?
 C17A C16A H16A 120.2 . . ?
 C16A C17A H17A 119.6 . . ?
 C16A C17A C18A 120.7(5) . . ?
 C18A C17A H17A 119.6 . . ?
 C13A C18A C17A 120.5(5) . . ?
 C13A C18A H18A 119.7 . . ?
 C17A C18A H18A 119.7 . . ?
 O2A B1A N1A 120.9(4) . . ?
 O2A B1A C6A 122.5(4) . . ?
 N1A B1A C6A 116.6(4) . . ?
 B1B O2B C3B 119.3(3) . . ?
 C11B O3B C12B 113.4(3) . . ?
 N2B N1B B1B 123.1(3) . . ?
 C1B N1B N2B 113.8(3) . . ?
 C1B N1B B1B 123.1(4) . . ?
 C4B N2B N1B 117.3(3) . . ?
 C2B N3B H3B 117(4) . . ?
 C11B N3B H3B 119(4) . . ?
 C11B N3B C2B 122.4(4) . . ?
 O1B C1B N1B 123.7(4) . . ?
 O1B C1B C2B 123.1(4) . . ?
 N1B C1B C2B 113.0(3) . . ?
 N3B C2B C1B 113.2(3) . . ?
 N3B C2B H2B 106.5 . . ?
 N3B C2B C3B 110.5(3) . . ?
 C1B C2B H2B 106.5 . . ?
 C1B C2B C3B 113.3(3) . . ?
 C3B C2B H2B 106.5 . . ?
 O2B C3B C2B 111.9(4) . . ?
 O2B C3B H3BA 109.2 . . ?
 O2B C3B H3BB 109.2 . . ?
 C2B C3B H3BA 109.2 . . ?
 C2B C3B H3BB 109.2 . . ?
 H3BA C3B H3BB 107.9 . . ?
 N2B C4B H4B 116.1 . . ?
 N2B C4B C5B 127.7(4) . . ?
 C5B C4B H4B 116.1 . . ?
 C6B C5B C4B 118.7(4) . . ?
 C6B C5B C10B 120.3(4) . . ?
 C10B C5B C4B 121.0(4) . . ?
 C5B C6B B1B 116.7(4) . . ?
 C7B C6B C5B 119.0(4) . . ?
 C7B C6B B1B 124.3(4) . . ?
 C6B C7B H7B 119.6 . . ?
 C8B C7B C6B 120.7(4) . . ?
 C8B C7B H7B 119.6 . . ?
 C7B C8B H8B 119.9 . . ?
 C7B C8B C9B 120.1(4) . . ?
 C9B C8B H8B 119.9 . . ?
 C8B C9B H9B 119.9 . . ?
 C10B C9B C8B 120.3(4) . . ?
 C10B C9B H9B 119.9 . . ?
 C5B C10B H10B 120.3 . . ?
 C9B C10B C5B 119.5(4) . . ?
 C9B C10B H10B 120.3 . . ?
 O4B C11B O3B 124.1(4) . . ?
 O4B C11B N3B 125.6(4) . . ?
 N3B C11B O3B 110.3(4) . . ?
 O3B C12B H12C 110.0 . . ?
 O3B C12B H12D 110.0 . . ?
 O3B C12B C13B 108.6(4) . . ?
 H12C C12B H12D 108.4 . . ?
 C13B C12B H12C 110.0 . . ?
 C13B C12B H12D 110.0 . . ?
 C14B C13B C12B 117.5(6) . . ?
 C18B C13B C12B 127.6(7) . . ?
 C18B C13B C14B 114.9(6) . . ?
 C13B C14B H14B 115.9 . . ?
 C15B C14B C13B 128.2(8) . . ?
 C15B C14B H14B 115.9 . . ?
 C14B C15B H15B 122.4 . . ?
 C16B C15B C14B 115.3(9) . . ?
 C16B C15B H15B 122.4 . . ?
 C15B C16B H16B 117.4 . . ?
 C15B C16B C17B 125.3(8) . . ?
 C17B C16B H16B 117.4 . . ?
 C16B C17B H17B 122.1 . . ?
 C16B C17B C18B 115.9(6) . . ?
 C18B C17B H17B 122.1 . . ?
 C13B C18B C17B 120.3(7) . . ?
 C13B C18B H18B 119.9 . . ?
 C17B C18B H18B 119.9 . . ?
 O2B B1B N1B 120.8(4) . . ?
 O2B B1B C6B 122.5(4) . . ?
 N1B B1B C6B 116.6(4) . . ?

loop_
  _geom_hbond_atom_site_label_D
  _geom_hbond_atom_site_label_H
  _geom_hbond_atom_site_label_A
  _geom_hbond_distance_DH
  _geom_hbond_distance_HA
  _geom_hbond_distance_DA
  _geom_hbond_angle_DHA
  _geom_hbond_site_symmetry_A
  _geom_hbond_publ_flag
 N3A H3A N2A 0.83(6) 2.27(6) 3.080(5) 165(5) 2_646 yes
 N3B H3B N2B 0.74(5) 2.26(5) 2.977(5) 164(5) 2 yes
 C3B H3BB O4B 0.99 2.31 2.958(5) 122.2 . yes

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 O1A C1A C2A N3A 8.9(6) . . . . ?
 O1A C1A C2A C3A 137.5(4) . . . . ?
 O3A C12A C13A C14A -71.3(8) . . . . ?
 O3A C12A C13A C18A 111.6(6) . . . . ?
 N1A N2A C4A C5A -1.0(6) . . . . ?
 N1A C1A C2A N3A -174.7(3) . . . . ?
 N1A C1A C2A C3A -46.1(4) . . . . ?
 N2A N1A C1A O1A 12.1(6) . . . . ?
 N2A N1A C1A C2A -164.4(3) . . . . ?
 N2A N1A B1A O2A -174.0(3) . . . . ?
 N2A N1A B1A C6A 6.8(5) . . . . ?
 N2A C4A C5A C6A 2.6(7) . . . . ?
 N2A C4A C5A C10A -178.0(4) . . . . ?
 N3A C2A C3A O2A -172.0(3) . . . . ?
 C1A N1A N2A C4A 174.5(4) . . . . ?
 C1A N1A B1A O2A 7.6(6) . . . . ?
 C1A N1A B1A C6A -171.6(3) . . . . ?
 C1A C2A C3A O2A 58.3(4) . . . . ?
 C2A N3A C11A O3A -179.0(4) . . . . ?
 C2A N3A C11A O4A 2.4(7) . . . . ?
 C3A O2A B1A N1A 5.3(6) . . . . ?
 C3A O2A B1A C6A -175.6(4) . . . . ?
 C4A C5A C6A C7A 179.9(4) . . . . ?
 C4A C5A C6A B1A 0.5(5) . . . . ?
 C4A C5A C10A C9A -179.9(4) . . . . ?
 C5A C6A C7A C8A 0.4(6) . . . . ?
 C5A C6A B1A O2A 176.1(4) . . . . ?
 C5A C6A B1A N1A -4.7(5) . . . . ?
 C6A C5A C10A C9A -0.6(6) . . . . ?
 C6A C7A C8A C9A -1.4(7) . . . . ?
 C7A C6A B1A O2A -3.2(6) . . . . ?
 C7A C6A B1A N1A 176.0(4) . . . . ?
 C7A C8A C9A C10A 1.3(7) . . . . ?
 C8A C9A C10A C5A -0.3(7) . . . . ?
 C10A C5A C6A C7A 0.5(6) . . . . ?
 C10A C5A C6A B1A -178.8(4) . . . . ?
 C11A O3A C12A C13A 167.0(5) . . . . ?
 C11A N3A C2A C1A -126.6(4) . . . . ?
 C11A N3A C2A C3A 105.1(4) . . . . ?
 C12A O3A C11A O4A -2.0(8) . . . . ?
 C12A O3A C11A N3A 179.4(5) . . . . ?
 C12A C13A C14A C15A -178.2(5) . . . . ?
 C12A C13A C18A C17A 178.4(4) . . . . ?
 C13A C14A C15A C16A -0.1(8) . . . . ?
 C14A C13A C18A C17A 1.3(7) . . . . ?
 C14A C15A C16A C17A 1.3(8) . . . . ?
 C15A C16A C17A C18A -1.2(7) . . . . ?
 C16A C17A C18A C13A -0.1(7) . . . . ?
 C18A C13A C14A C15A -1.1(7) . . . . ?
 B1A O2A C3A C2A -37.3(5) . . . . ?
 B1A N1A N2A C4A -4.0(6) . . . . ?
 B1A N1A C1A O1A -169.3(4) . . . . ?
 B1A N1A C1A C2A 14.2(5) . . . . ?
 B1A C6A C7A C8A 179.7(4) . . . . ?
 O1B C1B C2B N3B 21.7(6) . . . . ?
 O1B C1B C2B C3B 148.5(4) . . . . ?
 O3B C12B C13B C14B 94.0(7) . . . . ?
 O3B C12B C13B C18B -89.7(7) . . . . ?
 N1B N2B C4B C5B 0.0(7) . . . . ?
 N1B C1B C2B N3B -163.8(3) . . . . ?
 N1B C1B C2B C3B -37.1(5) . . . . ?
 N2B N1B C1B O1B 6.7(6) . . . . ?
 N2B N1B C1B C2B -167.8(3) . . . . ?
 N2B N1B B1B O2B -178.3(4) . . . . ?
 N2B N1B B1B C6B 1.0(6) . . . . ?
 N2B C4B C5B C6B 0.3(7) . . . . ?
 N2B C4B C5B C10B -178.2(4) . . . . ?
 N3B C2B C3B O2B 178.5(3) . . . . ?
 C1B N1B N2B C4B 178.4(4) . . . . ?
 C1B N1B B1B O2B 2.6(6) . . . . ?
 C1B N1B B1B C6B -178.1(3) . . . . ?
 C1B C2B C3B O2B 50.3(5) . . . . ?
 C2B N3B C11B O3B -179.1(4) . . . . ?
 C2B N3B C11B O4B 2.2(8) . . . . ?
 C3B O2B B1B N1B 11.6(6) . . . . ?
 C3B O2B B1B C6B -167.7(4) . . . . ?
 C4B C5B C6B C7B 179.1(4) . . . . ?
 C4B C5B C6B B1B 0.0(6) . . . . ?
 C4B C5B C10B C9B 178.6(4) . . . . ?
 C5B C6B C7B C8B 2.8(6) . . . . ?
 C5B C6B B1B O2B 178.7(4) . . . . ?
 C5B C6B B1B N1B -0.6(6) . . . . ?
 C6B C5B C10B C9B 0.0(6) . . . . ?
 C6B C7B C8B C9B -1.1(7) . . . . ?
 C7B C6B B1B O2B -0.4(7) . . . . ?
 C7B C6B B1B N1B -179.7(4) . . . . ?
 C7B C8B C9B C10B -1.2(7) . . . . ?
 C8B C9B C10B C5B 1.7(7) . . . . ?
 C10B C5B C6B C7B -2.3(6) . . . . ?
 C10B C5B C6B B1B 178.6(4) . . . . ?
 C11B O3B C12B C13B -179.6(5) . . . . ?
 C11B N3B C2B C1B 69.9(5) . . . . ?
 C11B N3B C2B C3B -58.3(5) . . . . ?
 C12B O3B C11B O4B 1.2(7) . . . . ?
 C12B O3B C11B N3B -177.5(5) . . . . ?
 C12B C13B C14B C15B 177.0(6) . . . . ?
 C12B C13B C18B C17B 179.7(5) . . . . ?
 C13B C14B C15B C16B 2.7(11) . . . . ?
 C14B C13B C18B C17B -3.9(8) . . . . ?
 C14B C15B C16B C17B -1.7(11) . . . . ?
 C15B C16B C17B C18B -1.7(9) . . . . ?
 C16B C17B C18B C13B 4.7(8) . . . . ?
 C18B C13B C14B C15B 0.2(10) . . . . ?
 B1B O2B C3B C2B -37.5(5) . . . . ?
 B1B N1B N2B C4B -0.7(6) . . . . ?
 B1B N1B C1B O1B -174.2(4) . . . . ?
 B1B N1B C1B C2B 11.4(5) . . . . ?
 B1B C6B C7B C8B -178.1(4) . . . . ?

_olex2_diffrn_ambient_temperature_device  'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
 'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id  'Vial 2 CBZ'
_olex2_submission_special_instructions  'No special instructions were received'

