data_1
_audit_creation_date               2019-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2014/7'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Bourhis, L.J., Dolomanov, O.V., Gildea, R.J., Howard, J.A.K., Puschmann, H.
 (2015). Acta Cryst. A71, 59-75.

Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           '2(C11 H16 B N O3)'
_chemical_formula_sum              'C22 H32 B2 N2 O6'
_chemical_formula_weight           442.11
_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        '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                     10.212(2)
_cell_length_b                     11.459(3)
_cell_length_c                     9.853(2)
_cell_angle_alpha                  90
_cell_angle_beta                   111.075(3)
_cell_angle_gamma                  90
_cell_volume                       1075.9(4)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      1548
_cell_measurement_temperature      296(2)
_cell_measurement_theta_max        24.028
_cell_measurement_theta_min        2.780
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      0.097
_exptl_absorpt_correction_T_max    ?
_exptl_absorpt_correction_T_min    ?
_exptl_absorpt_correction_type     ?
_exptl_absorpt_process_details     ?
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              ?
_exptl_crystal_density_diffrn      1.365
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         ?
_exptl_crystal_F_000               472
_exptl_crystal_size_max            ?
_exptl_crystal_size_mid            ?
_exptl_crystal_size_min            ?
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0416
_diffrn_reflns_av_unetI/netI       0.0382
_diffrn_reflns_Laue_measured_fraction_full  0.999
_diffrn_reflns_Laue_measured_fraction_max  0.988
_diffrn_reflns_limit_h_max         12
_diffrn_reflns_limit_h_min         -11
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -13
_diffrn_reflns_limit_l_max         11
_diffrn_reflns_limit_l_min         -11
_diffrn_reflns_number              7725
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.988
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           25.523
_diffrn_reflns_theta_min           2.137
_diffrn_ambient_temperature        296.15
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.999
_diffrn_measured_fraction_theta_max  0.988
_diffrn_measurement_device_type    ?
_diffrn_measurement_method         ?
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  1405
_reflns_number_total               1987
_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 v8.27A (Bruker, 2012)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution      'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max           0.440
_refine_diff_density_min           -0.469
_refine_diff_density_rms           0.054
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       150
_refine_ls_number_reflns           1987
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0799
_refine_ls_R_factor_gt             0.0526
_refine_ls_restrained_S_all        1.038
_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)+(0.0468P)²+1.1196P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1192
_refine_ls_wR_factor_ref           0.1331
_refine_special_details            ?
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00D(H00G,H00H), C00E(H00I,H00J), C00G(H00K,
 H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C008(H008), C00B(H00E), C00C(H00F)
2.c Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       iterative
_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
 O001 O 0.82148(18) 0.23040(15) 0.44199(17) 0.0284(4) Uani 1 1 d . . . . .
 O002 O 0.57705(17) 0.23663(15) 0.26850(19) 0.0311(5) Uani 1 1 d . . . . .
 O003 O 0.6819(2) 0.84135(16) 0.2620(2) 0.0393(5) Uani 1 1 d . . . . .
 H003 H 0.6048 0.8121 0.2475 0.059 Uiso 1 1 calc GR . . . .
 N004 N 0.7661(2) 0.17949(19) 0.1884(2) 0.0250(5) Uani 1 1 d . . . . .
 C005 C 0.7405(2) 0.4048(2) 0.2686(2) 0.0239(6) Uani 1 1 d . . . . .
 C006 C 0.8184(2) 0.4828(2) 0.3765(3) 0.0261(6) Uani 1 1 d . . . . .
 H006 H 0.8675 0.4542 0.4693 0.031 Uiso 1 1 calc R . . . .
 C007 C 0.7548(3) 0.6474(2) 0.2123(3) 0.0286(6) Uani 1 1 d . . . . .
 C008 C 0.8253(3) 0.6010(2) 0.3507(3) 0.0291(6) Uani 1 1 d . . . . .
 H008 H 0.8773 0.6500 0.4260 0.035 Uiso 1 1 calc R . . . .
 C009 C 0.6353(3) 0.1118(2) 0.1123(3) 0.0285(6) Uani 1 1 d . . . . .
 H00A H 0.6568 0.0313 0.0981 0.034 Uiso 1 1 calc R . . . .
 H00B H 0.5824 0.1461 0.0186 0.034 Uiso 1 1 calc R . . . .
 C00A C 0.5545(3) 0.1197(2) 0.2146(3) 0.0299(6) Uani 1 1 d . . . . .
 H00C H 0.4554 0.1049 0.1631 0.036 Uiso 1 1 calc R . . . .
 H00D H 0.5901 0.0639 0.2935 0.036 Uiso 1 1 calc R . . . .
 C00B C 0.6742(3) 0.4530(2) 0.1300(3) 0.0322(6) Uani 1 1 d . . . . .
 H00E H 0.6234 0.4041 0.0540 0.039 Uiso 1 1 calc R . . . .
 C00C C 0.6816(3) 0.5706(2) 0.1020(3) 0.0334(7) Uani 1 1 d . . . . .
 H00F H 0.6370 0.5986 0.0081 0.040 Uiso 1 1 calc R . . . .
 C00D C 0.7524(3) 0.7770(2) 0.1851(3) 0.0368(7) Uani 1 1 d . . . . .
 H00G H 0.8481 0.8050 0.2137 0.044 Uiso 1 1 calc R . . . .
 H00H H 0.7064 0.7913 0.0818 0.044 Uiso 1 1 calc R . . . .
 C00E C 0.8863(3) 0.1100(3) 0.2856(3) 0.0434(8) Uani 1 1 d . . . . .
 H00I H 0.8677 0.0272 0.2683 0.052 Uiso 1 1 calc R . . . .
 H00J H 0.9711 0.1289 0.2674 0.052 Uiso 1 1 calc R . . . .
 B00F B 0.7234(3) 0.2696(3) 0.2986(3) 0.0249(6) Uani 1 1 d . . . . .
 C00G C 0.9026(4) 0.1387(3) 0.4321(3) 0.0754(14) Uani 1 1 d . . . . .
 H00K H 0.8788 0.0709 0.4775 0.090 Uiso 1 1 calc R . . . .
 H00L H 1.0003 0.1573 0.4857 0.090 Uiso 1 1 calc R . . . .
 H004 H 0.788(3) 0.220(3) 0.121(3) 0.049(9) Uiso 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
 O001 B00F 1.477(3) . ?
 O001 C00G 1.363(3) . ?
 O002 C00A 1.429(3) . ?
 O002 B00F 1.465(3) . ?
 O003 C00D 1.424(3) . ?
 N004 C009 1.493(3) . ?
 N004 C00E 1.487(3) . ?
 N004 B00F 1.666(3) . ?
 C005 C006 1.398(3) . ?
 C005 C00B 1.402(3) . ?
 C005 B00F 1.598(4) . ?
 C006 C008 1.385(4) . ?
 C007 C008 1.398(4) . ?
 C007 C00C 1.389(4) . ?
 C007 C00D 1.508(4) . ?
 C009 C00A 1.517(3) . ?
 C00B C00C 1.383(4) . ?
 C00E C00G 1.431(4) . ?

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
 C00G O001 B00F 112.7(2) . . ?
 C00A O002 B00F 109.49(19) . . ?
 C009 N004 B00F 104.70(18) . . ?
 C00E N004 C009 115.3(2) . . ?
 C00E N004 B00F 105.16(19) . . ?
 C006 C005 C00B 115.7(2) . . ?
 C006 C005 B00F 123.3(2) . . ?
 C00B C005 B00F 121.0(2) . . ?
 C008 C006 C005 122.5(2) . . ?
 C008 C007 C00D 121.2(2) . . ?
 C00C C007 C008 117.7(2) . . ?
 C00C C007 C00D 121.0(2) . . ?
 C006 C008 C007 120.6(2) . . ?
 N004 C009 C00A 103.70(19) . . ?
 O002 C00A C009 104.4(2) . . ?
 C00C C00B C005 122.4(2) . . ?
 C00B C00C C007 120.9(2) . . ?
 O003 C00D C007 113.3(2) . . ?
 C00G C00E N004 107.2(2) . . ?
 O001 B00F N004 100.85(19) . . ?
 O001 B00F C005 113.0(2) . . ?
 O002 B00F O001 114.0(2) . . ?
 O002 B00F N004 101.22(19) . . ?
 O002 B00F C005 112.6(2) . . ?
 C005 B00F N004 114.2(2) . . ?
 O001 C00G C00E 113.3(2) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
