data_2k
_audit_creation_date               2019-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2016/6'
_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. (2008). Acta Cryst. A64, 112-122.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C22 H21 B N2 O'
_chemical_formula_sum              'C22 H21 B N2 O'
_chemical_formula_weight           340.22
_chemical_absolute_configuration   ?
_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' 0.0033 0.0016 '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' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 '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        'orthorhombic'
_space_group_IT_number             33
_space_group_name_H-M_alt          'P n a 21'
_space_group_name_Hall             'P 2c -2n'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, z+1/2'
 '-x+1/2, y+1/2, z+1/2'
 'x+1/2, -y+1/2, z'

_cell_length_a                     9.9494(7)
_cell_length_b                     9.2406(6)
_cell_length_c                     21.1428(13)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       1943.8(2)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9968
_cell_measurement_temperature      273(2)
_cell_measurement_theta_max        27.48
_cell_measurement_theta_min        3.01
_shelx_estimated_absorpt_T_max     0.993
_shelx_estimated_absorpt_T_min     0.979
_exptl_absorpt_coefficient_mu      0.071
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.5911
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1673 before and 0.0965 after correction. The Ratio of minimum to maximum transmission is 0.7928. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.163
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               720
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.1
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0984
_diffrn_reflns_av_unetI/netI       0.0379
_diffrn_reflns_Laue_measured_fraction_full  0.993
_diffrn_reflns_Laue_measured_fraction_max  0.993
_diffrn_reflns_limit_h_max         11
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         11
_diffrn_reflns_limit_k_min         -11
_diffrn_reflns_limit_l_max         25
_diffrn_reflns_limit_l_min         -25
_diffrn_reflns_number              49766
_diffrn_reflns_point_group_measured_fraction_full  0.994
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          25.018
_diffrn_reflns_theta_max           25.018
_diffrn_reflns_theta_min           3.009
_diffrn_ambient_temperature        273.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.993
_diffrn_measured_fraction_theta_max  0.993
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.944
_reflns_Friedel_fraction_full      0.994
_reflns_Friedel_fraction_max       0.994
_reflns_number_gt                  2907
_reflns_number_total               3392
_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 V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'XL (Sheldrick, 2008)'
_computing_structure_solution      'XS (Sheldrick, 2008)'
_refine_diff_density_max           0.092
_refine_diff_density_min           -0.112
_refine_diff_density_rms           0.025
_refine_ls_abs_structure_details
;
 Flack x determined using 1260 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.0(9)
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.083
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       238
_refine_ls_number_reflns           3392
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0478
_refine_ls_R_factor_gt             0.0374
_refine_ls_restrained_S_all        1.083
_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)+(0.0456P)²+0.1177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0894
_refine_ls_wR_factor_ref           0.0966
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C16(H16), C22(H22), C21(H21), C20(H20), C15(H15), C14(H14),
 C7(H7), C8(H8), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C4(H4a,H4b,H4c), C5(H5a,H5b,H5c)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_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 0.3802(2) 0.5325(2) 0.48758(11) 0.0696(6) Uani 1 1 d . . . . .
 N1 N 0.1820(2) 0.7456(3) 0.54589(10) 0.0543(6) Uani 1 1 d . . . . .
 H1 H 0.121695 0.679277 0.543106 0.065 Uiso 1 1 calc R . . . .
 N2 N 0.3445(2) 0.9000(2) 0.49675(10) 0.0513(5) Uani 1 1 d . . . . .
 H2 H 0.385038 0.930318 0.463361 0.062 Uiso 1 1 calc R . . . .
 C12 C 0.4360(4) 0.4615(4) 0.5408(2) 0.0986(13) Uani 1 1 d . . . . .
 H12A H 0.365484 0.416300 0.564663 0.148 Uiso 1 1 calc GR . . . .
 H12B H 0.481660 0.530794 0.566879 0.148 Uiso 1 1 calc GR . . . .
 H12C H 0.498634 0.389197 0.526828 0.148 Uiso 1 1 calc GR . . . .
 C11 C 0.2800(3) 0.4650(3) 0.45476(13) 0.0547(6) Uani 1 1 d . . . . .
 C6 C 0.1954(3) 0.5567(3) 0.42081(11) 0.0502(6) Uani 1 1 d . . . . .
 C1 C 0.2141(3) 0.7168(3) 0.42501(12) 0.0497(6) Uani 1 1 d . . . . .
 B1 B 0.2500(3) 0.7873(3) 0.49010(14) 0.0489(7) Uani 1 1 d . . . . .
 C13 C 0.2071(3) 0.8057(3) 0.60506(12) 0.0503(6) Uani 1 1 d . . . . .
 C18 C 0.3038(3) 0.9185(3) 0.60870(12) 0.0484(6) Uani 1 1 d . . . . .
 C17 C 0.3305(3) 0.9826(3) 0.66837(13) 0.0617(8) Uani 1 1 d . . . . .
 C16 C 0.2594(4) 0.9326(4) 0.72163(14) 0.0783(10) Uani 1 1 d . . . . .
 H16 H 0.274676 0.974785 0.760908 0.094 Uiso 1 1 calc R . . . .
 C22 C 0.4301(4) 1.0927(4) 0.67119(17) 0.0757(10) Uani 1 1 d . . . . .
 H22 H 0.447249 1.138593 0.709481 0.091 Uiso 1 1 calc R . . . .
 C21 C 0.5000(4) 1.1317(4) 0.61928(19) 0.0766(9) Uani 1 1 d . . . . .
 H21 H 0.566755 1.201733 0.622791 0.092 Uiso 1 1 calc R . . . .
 C20 C 0.4742(3) 1.0691(3) 0.56031(15) 0.0610(7) Uani 1 1 d . . . . .
 H20 H 0.523471 1.097816 0.525083 0.073 Uiso 1 1 calc R . . . .
 C19 C 0.3760(3) 0.9650(3) 0.55437(12) 0.0484(6) Uani 1 1 d . . . . .
 C15 C 0.1686(4) 0.8232(4) 0.71624(15) 0.0810(10) Uani 1 1 d . . . . .
 H15 H 0.123864 0.790394 0.752111 0.097 Uiso 1 1 calc R . . . .
 C14 C 0.1417(4) 0.7601(4) 0.65854(14) 0.0691(8) Uani 1 1 d . . . . .
 H14 H 0.078719 0.686033 0.655860 0.083 Uiso 1 1 calc R . . . .
 C2 C 0.1904(3) 0.7979(3) 0.37513(13) 0.0547(7) Uani 1 1 d . . . . .
 C3 C 0.1616(3) 0.8762(3) 0.32595(13) 0.0627(8) Uani 1 1 d . . . . .
 C4 C 0.2667(4) 0.9143(5) 0.27731(17) 0.0999(14) Uani 1 1 d . . . . .
 H4A H 0.350979 0.871236 0.288987 0.150 Uiso 1 1 calc GR . . . .
 H4B H 0.276646 1.017502 0.275289 0.150 Uiso 1 1 calc GR . . . .
 H4C H 0.239480 0.878292 0.236688 0.150 Uiso 1 1 calc GR . . . .
 C5 C 0.0216(4) 0.9310(4) 0.31534(19) 0.0914(11) Uani 1 1 d . . . . .
 H5A H -0.035826 0.897218 0.348706 0.137 Uiso 1 1 calc GR . . . .
 H5B H -0.011186 0.896008 0.275474 0.137 Uiso 1 1 calc GR . . . .
 H5C H 0.022177 1.034891 0.315057 0.137 Uiso 1 1 calc GR . . . .
 C7 C 0.0941(3) 0.4940(3) 0.38473(13) 0.0635(8) Uani 1 1 d . . . . .
 H7 H 0.036310 0.553057 0.361718 0.076 Uiso 1 1 calc R . . . .
 C8 C 0.0775(4) 0.3443(4) 0.38241(16) 0.0769(9) Uani 1 1 d . . . . .
 H8 H 0.009513 0.303796 0.357952 0.092 Uiso 1 1 calc R . . . .
 C9 C 0.1626(4) 0.2574(4) 0.41660(17) 0.0793(10) Uani 1 1 d . . . . .
 H9 H 0.152049 0.157486 0.415060 0.095 Uiso 1 1 calc R . . . .
 C10 C 0.2629(3) 0.3160(3) 0.45305(16) 0.0689(8) Uani 1 1 d . . . . .
 H10 H 0.319192 0.256144 0.476482 0.083 Uiso 1 1 calc R . . . .


_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 C12 1.415(4) . ?
 O1 C11 1.365(3) . ?
 N1 H1 0.8600 . ?
 N1 B1 1.413(4) . ?
 N1 C13 1.391(3) . ?
 N2 H2 0.8600 . ?
 N2 B1 1.410(4) . ?
 N2 C19 1.394(3) . ?
 C12 H12A 0.9600 . ?
 C12 H12B 0.9600 . ?
 C12 H12C 0.9600 . ?
 C11 C6 1.393(4) . ?
 C11 C10 1.388(4) . ?
 C6 C1 1.494(4) . ?
 C6 C7 1.390(4) . ?
 C1 B1 1.564(4) . ?
 C1 C2 1.315(4) . ?
 C13 C18 1.421(4) . ?
 C13 C14 1.371(4) . ?
 C18 C17 1.419(4) . ?
 C18 C19 1.421(4) . ?
 C17 C16 1.408(5) . ?
 C17 C22 1.421(5) . ?
 C16 H16 0.9300 . ?
 C16 C15 1.361(5) . ?
 C22 H22 0.9300 . ?
 C22 C21 1.349(5) . ?
 C21 H21 0.9300 . ?
 C21 C20 1.398(5) . ?
 C20 H20 0.9300 . ?
 C20 C19 1.377(4) . ?
 C15 H15 0.9300 . ?
 C15 C14 1.378(5) . ?
 C14 H14 0.9300 . ?
 C2 C3 1.299(4) . ?
 C3 C4 1.508(5) . ?
 C3 C5 1.499(5) . ?
 C4 H4A 0.9600 . ?
 C4 H4B 0.9600 . ?
 C4 H4C 0.9600 . ?
 C5 H5A 0.9600 . ?
 C5 H5B 0.9600 . ?
 C5 H5C 0.9600 . ?
 C7 H7 0.9300 . ?
 C7 C8 1.394(5) . ?
 C8 H8 0.9300 . ?
 C8 C9 1.373(5) . ?
 C9 H9 0.9300 . ?
 C9 C10 1.373(5) . ?
 C10 H10 0.9300 . ?

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
 C11 O1 C12 118.6(2) . . ?
 B1 N1 H1 118.1 . . ?
 C13 N1 H1 118.1 . . ?
 C13 N1 B1 123.8(2) . . ?
 B1 N2 H2 118.1 . . ?
 C19 N2 H2 118.1 . . ?
 C19 N2 B1 123.7(2) . . ?
 O1 C12 H12A 109.5 . . ?
 O1 C12 H12B 109.5 . . ?
 O1 C12 H12C 109.5 . . ?
 H12A C12 H12B 109.5 . . ?
 H12A C12 H12C 109.5 . . ?
 H12B C12 H12C 109.5 . . ?
 O1 C11 C6 115.2(2) . . ?
 O1 C11 C10 123.8(3) . . ?
 C10 C11 C6 121.0(3) . . ?
 C11 C6 C1 119.7(2) . . ?
 C7 C6 C11 117.9(3) . . ?
 C7 C6 C1 122.4(3) . . ?
 C6 C1 B1 119.6(2) . . ?
 C2 C1 C6 119.6(2) . . ?
 C2 C1 B1 120.6(3) . . ?
 N1 B1 C1 120.8(2) . . ?
 N2 B1 N1 115.9(2) . . ?
 N2 B1 C1 123.2(2) . . ?
 N1 C13 C18 117.6(2) . . ?
 C14 C13 N1 122.3(3) . . ?
 C14 C13 C18 120.1(3) . . ?
 C13 C18 C19 121.4(2) . . ?
 C17 C18 C13 118.8(2) . . ?
 C17 C18 C19 119.8(3) . . ?
 C18 C17 C22 117.8(3) . . ?
 C16 C17 C18 118.7(3) . . ?
 C16 C17 C22 123.5(3) . . ?
 C17 C16 H16 119.6 . . ?
 C15 C16 C17 120.7(3) . . ?
 C15 C16 H16 119.6 . . ?
 C17 C22 H22 119.4 . . ?
 C21 C22 C17 121.1(3) . . ?
 C21 C22 H22 119.4 . . ?
 C22 C21 H21 119.3 . . ?
 C22 C21 C20 121.4(3) . . ?
 C20 C21 H21 119.3 . . ?
 C21 C20 H20 120.0 . . ?
 C19 C20 C21 120.0(3) . . ?
 C19 C20 H20 120.0 . . ?
 N2 C19 C18 117.5(2) . . ?
 C20 C19 N2 122.7(3) . . ?
 C20 C19 C18 119.8(2) . . ?
 C16 C15 H15 119.4 . . ?
 C16 C15 C14 121.1(3) . . ?
 C14 C15 H15 119.4 . . ?
 C13 C14 C15 120.6(3) . . ?
 C13 C14 H14 119.7 . . ?
 C15 C14 H14 119.7 . . ?
 C3 C2 C1 177.5(3) . . ?
 C2 C3 C4 121.5(3) . . ?
 C2 C3 C5 120.9(3) . . ?
 C5 C3 C4 117.6(3) . . ?
 C3 C4 H4A 109.5 . . ?
 C3 C4 H4B 109.5 . . ?
 C3 C4 H4C 109.5 . . ?
 H4A C4 H4B 109.5 . . ?
 H4A C4 H4C 109.5 . . ?
 H4B C4 H4C 109.5 . . ?
 C3 C5 H5A 109.5 . . ?
 C3 C5 H5B 109.5 . . ?
 C3 C5 H5C 109.5 . . ?
 H5A C5 H5B 109.5 . . ?
 H5A C5 H5C 109.5 . . ?
 H5B C5 H5C 109.5 . . ?
 C6 C7 H7 119.4 . . ?
 C6 C7 C8 121.2(3) . . ?
 C8 C7 H7 119.4 . . ?
 C7 C8 H8 120.4 . . ?
 C9 C8 C7 119.3(3) . . ?
 C9 C8 H8 120.4 . . ?
 C8 C9 H9 119.5 . . ?
 C10 C9 C8 120.9(3) . . ?
 C10 C9 H9 119.5 . . ?
 C11 C10 H10 120.2 . . ?
 C9 C10 C11 119.7(3) . . ?
 C9 C10 H10 120.2 . . ?

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
 O1 C11 C6 C1 -3.1(3) . . . . ?
 O1 C11 C6 C7 177.9(2) . . . . ?
 O1 C11 C10 C9 -177.3(3) . . . . ?
 N1 C13 C18 C17 179.5(2) . . . . ?
 N1 C13 C18 C19 -2.2(4) . . . . ?
 N1 C13 C14 C15 -179.5(3) . . . . ?
 C12 O1 C11 C6 155.7(3) . . . . ?
 C12 O1 C11 C10 -25.8(4) . . . . ?
 C11 C6 C1 B1 -39.5(4) . . . . ?
 C11 C6 C1 C2 145.6(3) . . . . ?
 C11 C6 C7 C8 -0.1(4) . . . . ?
 C6 C11 C10 C9 1.1(5) . . . . ?
 C6 C1 B1 N1 -44.5(4) . . . . ?
 C6 C1 B1 N2 139.2(3) . . . . ?
 C6 C7 C8 C9 0.2(5) . . . . ?
 C1 C6 C7 C8 -179.0(3) . . . . ?
 B1 N1 C13 C18 2.1(4) . . . . ?
 B1 N1 C13 C14 -178.3(3) . . . . ?
 B1 N2 C19 C18 -2.8(3) . . . . ?
 B1 N2 C19 C20 176.1(2) . . . . ?
 C13 N1 B1 N2 -2.2(4) . . . . ?
 C13 N1 B1 C1 -178.8(2) . . . . ?
 C13 C18 C17 C16 -0.5(4) . . . . ?
 C13 C18 C17 C22 178.4(3) . . . . ?
 C13 C18 C19 N2 2.6(3) . . . . ?
 C13 C18 C19 C20 -176.4(2) . . . . ?
 C18 C13 C14 C15 0.2(5) . . . . ?
 C18 C17 C16 C15 1.2(5) . . . . ?
 C18 C17 C22 C21 -2.2(5) . . . . ?
 C17 C18 C19 N2 -179.1(2) . . . . ?
 C17 C18 C19 C20 1.9(4) . . . . ?
 C17 C16 C15 C14 -1.2(6) . . . . ?
 C17 C22 C21 C20 2.2(5) . . . . ?
 C16 C17 C22 C21 176.7(3) . . . . ?
 C16 C15 C14 C13 0.5(6) . . . . ?
 C22 C17 C16 C15 -177.7(3) . . . . ?
 C22 C21 C20 C19 -0.2(5) . . . . ?
 C21 C20 C19 N2 179.2(3) . . . . ?
 C21 C20 C19 C18 -1.9(4) . . . . ?
 C19 N2 B1 N1 2.6(4) . . . . ?
 C19 N2 B1 C1 179.1(2) . . . . ?
 C19 C18 C17 C16 -178.8(3) . . . . ?
 C19 C18 C17 C22 0.1(4) . . . . ?
 C14 C13 C18 C17 -0.2(4) . . . . ?
 C14 C13 C18 C19 178.1(3) . . . . ?
 C2 C1 B1 N1 130.3(3) . . . . ?
 C2 C1 B1 N2 -46.0(4) . . . . ?
 C7 C6 C1 B1 139.4(3) . . . . ?
 C7 C6 C1 C2 -35.5(4) . . . . ?
 C7 C8 C9 C10 0.2(5) . . . . ?
 C8 C9 C10 C11 -0.9(5) . . . . ?
 C10 C11 C6 C1 178.4(3) . . . . ?
 C10 C11 C6 C7 -0.6(4) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

#===END  

data_2q
_audit_creation_date               2019-03-18
_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. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C19 H22 B Cl N2'
_chemical_formula_sum              'C19 H22 B Cl N2'
_chemical_formula_weight           324.64
_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' 0.0033 0.0016 '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' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 '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/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     14.7636(14)
_cell_length_b                     5.5546(5)
_cell_length_c                     22.076(2)
_cell_angle_alpha                  90
_cell_angle_beta                   101.332(3)
_cell_angle_gamma                  90
_cell_volume                       1775.0(3)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      9887
_cell_measurement_temperature      273(2)
_cell_measurement_theta_max        27.46
_cell_measurement_theta_min        3.06
_shelx_estimated_absorpt_T_max     0.979
_shelx_estimated_absorpt_T_min     0.938
_exptl_absorpt_coefficient_mu      0.215
_exptl_absorpt_correction_T_max    0.7456
_exptl_absorpt_correction_T_min    0.6258
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1448 before and 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.8393. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.215
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         needle
_exptl_crystal_F_000               688
_exptl_crystal_size_max            0.3
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.1
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0591
_diffrn_reflns_av_unetI/netI       0.0233
_diffrn_reflns_Laue_measured_fraction_full  0.996
_diffrn_reflns_Laue_measured_fraction_max  0.996
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         6
_diffrn_reflns_limit_k_min         -6
_diffrn_reflns_limit_l_max         26
_diffrn_reflns_limit_l_min         -26
_diffrn_reflns_number              46162
_diffrn_reflns_point_group_measured_fraction_full  0.996
_diffrn_reflns_point_group_measured_fraction_max  0.996
_diffrn_reflns_theta_full          25.023
_diffrn_reflns_theta_max           25.023
_diffrn_reflns_theta_min           2.562
_diffrn_ambient_temperature        273.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.996
_diffrn_measured_fraction_theta_max  0.996
_diffrn_measurement_device_type    'Bruker APEX-II CCD'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2490
_reflns_number_total               3130
_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 V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'XS (Sheldrick, 2008)'
_refine_diff_density_max           0.168
_refine_diff_density_min           -0.232
_refine_diff_density_rms           0.032
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.072
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       210
_refine_ls_number_reflns           3130
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0556
_refine_ls_R_factor_gt             0.0415
_refine_ls_restrained_S_all        1.072
_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)+(0.0482P)²+0.5993P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1046
_refine_ls_wR_factor_ref           0.1177
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C19(H19), C18(H18), C17(H17), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       direct
_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
 Cl1 Cl 0.52037(4) -0.24797(11) 0.12127(3) 0.0898(3) Uani 1 1 d . . . . .
 N1 N 0.17027(10) 0.9226(3) 0.25776(6) 0.0484(4) Uani 1 1 d . . . . .
 H1 H 0.134360 0.937801 0.222243 0.058 Uiso 1 1 calc R . . . .
 N2 N 0.29406(10) 0.7175(3) 0.32455(6) 0.0462(4) Uani 1 1 d . . . . .
 H2 H 0.336094 0.608058 0.330469 0.055 Uiso 1 1 calc R . . . .
 C19 C 0.26764(15) 1.1802(4) 0.47009(8) 0.0603(5) Uani 1 1 d . . . . .
 H19 H 0.263056 1.283594 0.502490 0.072 Uiso 1 1 calc R . . . .
 C14 C 0.20855(12) 1.2125(3) 0.41213(8) 0.0487(4) Uani 1 1 d . . . . .
 C15 C 0.21782(11) 1.0516(3) 0.36334(7) 0.0413(4) Uani 1 1 d . . . . .
 C10 C 0.15887(11) 1.0819(3) 0.30440(7) 0.0434(4) Uani 1 1 d . . . . .
 B1 B 0.23728(13) 0.7375(3) 0.26524(9) 0.0432(4) Uani 1 1 d . . . . .
 C5 C 0.25000(11) 0.5734(3) 0.21008(7) 0.0440(4) Uani 1 1 d . . . . .
 C6 C 0.33159(13) 0.4029(3) 0.21761(8) 0.0528(5) Uani 1 1 d . . . . .
 H6A H 0.387955 0.496597 0.228044 0.063 Uiso 1 1 calc R . . . .
 H6B H 0.329303 0.296560 0.252127 0.063 Uiso 1 1 calc R . . . .
 C7 C 0.33647(13) 0.2510(3) 0.16158(8) 0.0535(5) Uani 1 1 d . . . . .
 H7A H 0.336651 0.356237 0.126551 0.064 Uiso 1 1 calc R . . . .
 H7B H 0.281558 0.151292 0.152068 0.064 Uiso 1 1 calc R . . . .
 C8 C 0.42125(13) 0.0899(4) 0.17024(9) 0.0601(5) Uani 1 1 d . . . . .
 H8A H 0.476496 0.188448 0.179333 0.072 Uiso 1 1 calc R . . . .
 H8B H 0.421397 -0.016574 0.205087 0.072 Uiso 1 1 calc R . . . .
 C9 C 0.42257(16) -0.0557(5) 0.11408(11) 0.0825(8) Uani 1 1 d . . . . .
 H9A H 0.421817 0.051924 0.079387 0.099 Uiso 1 1 calc R . . . .
 H9B H 0.366964 -0.152920 0.105146 0.099 Uiso 1 1 calc R . . . .
 C4 C 0.18994(12) 0.5870(3) 0.15771(7) 0.0442(4) Uani 1 1 d . . . . .
 C2 C 0.12834(12) 0.5984(3) 0.10662(7) 0.0456(4) Uani 1 1 d . . . . .
 C3 C 0.04650(14) 0.4310(4) 0.09488(10) 0.0687(6) Uani 1 1 d . . . . .
 H3A H 0.048220 0.328699 0.130133 0.103 Uiso 1 1 calc GR . . . .
 H3B H 0.048612 0.334037 0.059184 0.103 Uiso 1 1 calc GR . . . .
 H3C H -0.009491 0.523609 0.087826 0.103 Uiso 1 1 calc GR . . . .
 C1 C 0.13554(15) 0.7716(4) 0.05555(9) 0.0632(5) Uani 1 1 d . . . . .
 H1A H 0.187695 0.875560 0.068469 0.095 Uiso 1 1 calc GR . . . .
 H1B H 0.080201 0.866419 0.046024 0.095 Uiso 1 1 calc GR . . . .
 H1C H 0.143310 0.683488 0.019506 0.095 Uiso 1 1 calc GR . . . .
 C18 C 0.33105(15) 1.0004(4) 0.47915(8) 0.0624(5) Uani 1 1 d . . . . .
 H18 H 0.369287 0.983270 0.517753 0.075 Uiso 1 1 calc R . . . .
 C17 C 0.34033(13) 0.8400(4) 0.43180(8) 0.0535(5) Uani 1 1 d . . . . .
 H17 H 0.383444 0.716092 0.439255 0.064 Uiso 1 1 calc R . . . .
 C16 C 0.28525(11) 0.8668(3) 0.37410(7) 0.0425(4) Uani 1 1 d . . . . .
 C13 C 0.14159(14) 1.3971(4) 0.39998(9) 0.0592(5) Uani 1 1 d . . . . .
 H13 H 0.134843 1.503621 0.431299 0.071 Uiso 1 1 calc R . . . .
 C12 C 0.08720(14) 1.4209(4) 0.34338(10) 0.0626(5) Uani 1 1 d . . . . .
 H12 H 0.043854 1.544392 0.336403 0.075 Uiso 1 1 calc R . . . .
 C11 C 0.09473(13) 1.2641(3) 0.29524(9) 0.0564(5) Uani 1 1 d . . . . .
 H11 H 0.056191 1.283065 0.256810 0.068 Uiso 1 1 calc R . . . .


_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
 Cl1 C9 1.778(2) . ?
 N1 H1 0.8600 . ?
 N1 C10 1.392(2) . ?
 N1 B1 1.414(2) . ?
 N2 H2 0.8600 . ?
 N2 B1 1.413(2) . ?
 N2 C16 1.399(2) . ?
 C19 H19 0.9300 . ?
 C19 C14 1.411(3) . ?
 C19 C18 1.356(3) . ?
 C14 C15 1.427(2) . ?
 C14 C13 1.413(3) . ?
 C15 C10 1.426(2) . ?
 C15 C16 1.417(2) . ?
 C10 C11 1.374(2) . ?
 B1 C5 1.562(2) . ?
 C5 C6 1.515(2) . ?
 C5 C4 1.314(2) . ?
 C6 H6A 0.9700 . ?
 C6 H6B 0.9700 . ?
 C6 C7 1.511(2) . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C7 C8 1.520(2) . ?
 C8 H8A 0.9700 . ?
 C8 H8B 0.9700 . ?
 C8 C9 1.483(3) . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C4 C2 1.304(2) . ?
 C2 C3 1.506(3) . ?
 C2 C1 1.502(3) . ?
 C3 H3A 0.9600 . ?
 C3 H3B 0.9600 . ?
 C3 H3C 0.9600 . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 0.9600 . ?
 C18 H18 0.9300 . ?
 C18 C17 1.401(3) . ?
 C17 H17 0.9300 . ?
 C17 C16 1.378(2) . ?
 C13 H13 0.9300 . ?
 C13 C12 1.353(3) . ?
 C12 H12 0.9300 . ?
 C12 C11 1.395(3) . ?
 C11 H11 0.9300 . ?

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
 C10 N1 H1 118.0 . . ?
 C10 N1 B1 123.99(14) . . ?
 B1 N1 H1 118.0 . . ?
 B1 N2 H2 118.4 . . ?
 C16 N2 H2 118.4 . . ?
 C16 N2 B1 123.24(15) . . ?
 C14 C19 H19 119.6 . . ?
 C18 C19 H19 119.6 . . ?
 C18 C19 C14 120.86(18) . . ?
 C19 C14 C15 118.10(17) . . ?
 C19 C14 C13 123.30(17) . . ?
 C13 C14 C15 118.59(16) . . ?
 C10 C15 C14 118.89(16) . . ?
 C16 C15 C14 119.70(15) . . ?
 C16 C15 C10 121.41(14) . . ?
 N1 C10 C15 117.32(15) . . ?
 C11 C10 N1 122.63(15) . . ?
 C11 C10 C15 120.04(15) . . ?
 N1 B1 C5 121.46(15) . . ?
 N2 B1 N1 116.07(15) . . ?
 N2 B1 C5 122.41(16) . . ?
 C6 C5 B1 119.59(14) . . ?
 C4 C5 B1 119.26(15) . . ?
 C4 C5 C6 121.14(15) . . ?
 C5 C6 H6A 108.5 . . ?
 C5 C6 H6B 108.5 . . ?
 H6A C6 H6B 107.5 . . ?
 C7 C6 C5 115.09(14) . . ?
 C7 C6 H6A 108.5 . . ?
 C7 C6 H6B 108.5 . . ?
 C6 C7 H7A 108.9 . . ?
 C6 C7 H7B 108.9 . . ?
 C6 C7 C8 113.37(15) . . ?
 H7A C7 H7B 107.7 . . ?
 C8 C7 H7A 108.9 . . ?
 C8 C7 H7B 108.9 . . ?
 C7 C8 H8A 109.4 . . ?
 C7 C8 H8B 109.4 . . ?
 H8A C8 H8B 108.0 . . ?
 C9 C8 C7 111.20(16) . . ?
 C9 C8 H8A 109.4 . . ?
 C9 C8 H8B 109.4 . . ?
 Cl1 C9 H9A 108.9 . . ?
 Cl1 C9 H9B 108.9 . . ?
 C8 C9 Cl1 113.37(15) . . ?
 C8 C9 H9A 108.9 . . ?
 C8 C9 H9B 108.9 . . ?
 H9A C9 H9B 107.7 . . ?
 C2 C4 C5 178.25(19) . . ?
 C4 C2 C3 121.24(17) . . ?
 C4 C2 C1 122.71(17) . . ?
 C1 C2 C3 116.03(16) . . ?
 C2 C3 H3A 109.5 . . ?
 C2 C3 H3B 109.5 . . ?
 C2 C3 H3C 109.5 . . ?
 H3A C3 H3B 109.5 . . ?
 H3A C3 H3C 109.5 . . ?
 H3B C3 H3C 109.5 . . ?
 C2 C1 H1A 109.5 . . ?
 C2 C1 H1B 109.5 . . ?
 C2 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 C19 C18 H18 119.2 . . ?
 C19 C18 C17 121.61(17) . . ?
 C17 C18 H18 119.2 . . ?
 C18 C17 H17 120.2 . . ?
 C16 C17 C18 119.64(18) . . ?
 C16 C17 H17 120.2 . . ?
 N2 C16 C15 117.94(14) . . ?
 C17 C16 N2 122.00(16) . . ?
 C17 C16 C15 120.06(15) . . ?
 C14 C13 H13 119.6 . . ?
 C12 C13 C14 120.83(17) . . ?
 C12 C13 H13 119.6 . . ?
 C13 C12 H12 119.3 . . ?
 C13 C12 C11 121.40(18) . . ?
 C11 C12 H12 119.3 . . ?
 C10 C11 C12 120.25(17) . . ?
 C10 C11 H11 119.9 . . ?
 C12 C11 H11 119.9 . . ?

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
 N1 C10 C11 C12 -179.02(17) . . . . ?
 N1 B1 C5 C6 170.87(17) . . . . ?
 N1 B1 C5 C4 -8.7(3) . . . . ?
 N2 B1 C5 C6 -6.4(3) . . . . ?
 N2 B1 C5 C4 174.10(17) . . . . ?
 C19 C14 C15 C10 -179.82(16) . . . . ?
 C19 C14 C15 C16 -0.2(2) . . . . ?
 C19 C14 C13 C12 179.49(19) . . . . ?
 C19 C18 C17 C16 1.3(3) . . . . ?
 C14 C19 C18 C17 -0.2(3) . . . . ?
 C14 C15 C10 N1 179.57(15) . . . . ?
 C14 C15 C10 C11 0.2(2) . . . . ?
 C14 C15 C16 N2 -178.07(14) . . . . ?
 C14 C15 C16 C17 1.3(2) . . . . ?
 C14 C13 C12 C11 0.4(3) . . . . ?
 C15 C14 C13 C12 0.1(3) . . . . ?
 C15 C10 C11 C12 0.3(3) . . . . ?
 C10 N1 B1 N2 0.7(3) . . . . ?
 C10 N1 B1 C5 -176.71(15) . . . . ?
 C10 C15 C16 N2 1.6(2) . . . . ?
 C10 C15 C16 C17 -179.10(16) . . . . ?
 B1 N1 C10 C15 -1.1(2) . . . . ?
 B1 N1 C10 C11 178.20(18) . . . . ?
 B1 N2 C16 C15 -2.0(2) . . . . ?
 B1 N2 C16 C17 178.64(17) . . . . ?
 B1 C5 C6 C7 179.35(16) . . . . ?
 C5 C6 C7 C8 177.73(17) . . . . ?
 C6 C7 C8 C9 179.8(2) . . . . ?
 C7 C8 C9 Cl1 179.91(17) . . . . ?
 C4 C5 C6 C7 -1.1(3) . . . . ?
 C18 C19 C14 C15 -0.4(3) . . . . ?
 C18 C19 C14 C13 -179.70(19) . . . . ?
 C18 C17 C16 N2 177.52(16) . . . . ?
 C18 C17 C16 C15 -1.8(3) . . . . ?
 C16 N2 B1 N1 0.9(3) . . . . ?
 C16 N2 B1 C5 178.32(15) . . . . ?
 C16 C15 C10 N1 -0.1(2) . . . . ?
 C16 C15 C10 C11 -179.39(16) . . . . ?
 C13 C14 C15 C10 -0.5(2) . . . . ?
 C13 C14 C15 C16 179.19(16) . . . . ?
 C13 C12 C11 C10 -0.6(3) . . . . ?

_olex2_submission_special_instructions  'No special instructions were received'

