# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lucia2
_database_code_depnum_ccdc_archive 'CCDC 1880524'
loop_
_audit_author_name
_audit_author_address
'Daniel Paley'
;Columbia University
United States of America
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_audit_creation_date             2018-08-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 B N O5'
_chemical_formula_sum            'C14 H22 B N O5'
_chemical_formula_weight         295.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c14 h22 b n o5'
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/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                   24.3090(11)
_cell_length_b                   6.3645(2)
_cell_length_c                   31.2582(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.597(5)
_cell_angle_gamma                90
_cell_volume                     4527.0(4)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.0580
_cell_measurement_theta_min      3.8600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.714
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 4 0 0.1469
-1 0 -1 0.0067
1 0 -1 0.0141
-1 0 1 0.0180
-1 -4 2 0.1766
1 0 1 0.0030

_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.036
_exptl_crystal_size_min          0.01
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0047 4.1313 0.1173 0.0365 -0.0516 0.9980
-1.0015 -0.0005 -0.9990 -0.0559 0.0820 0.0056
0.9998 -0.0000 -1.0004 0.0657 0.0229 -0.0014
-0.9998 0.0000 1.0004 -0.0657 -0.0229 0.0014
-0.6709 -4.1028 2.3891 -0.0892 -0.0603 -0.9942
1.0015 0.0005 0.9990 0.0559 -0.0820 -0.0056

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0748
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            29418
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.785
_diffrn_reflns_theta_min         3.885
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  74.00   1.00    6.00    --   37.70 -99.00-150.00   52
  2  ω      6.00  33.00   1.00    6.00    --   37.70 -57.00  60.00   27
  3  ω    -59.00  32.00   1.00    6.00    --  -34.58  19.00-120.00   91
  4  ω    -64.00  35.00   1.00    6.00    --  -34.58  19.00 150.00   99
  5  ω     76.00 110.00   1.00    6.00    --   37.70 178.00-150.00   34
  6  ω    -51.00 -16.00   1.00    6.00    --  -37.78  37.00  60.00   35
  7  ω     -6.00  31.00   1.00    6.00    --  -37.78  37.00  60.00   37
  8  ω   -109.00 -82.00   1.00    6.00    --  -37.78-178.00-180.00   27
  9  ω     43.00 120.00   1.00   30.00    --  111.00 -45.00   0.00   77
 10  ω     73.00 178.00   1.00   30.00    --  111.00  15.00 -90.00  105
 11  ω     58.00 108.00   1.00   30.00    --  111.00 -94.00 -90.00   50
 12  ω    115.00 174.00   1.00   30.00    --  111.00 111.00  90.00   59
 13  ω     79.00 129.00   1.00   30.00    --  111.00 -61.00 -90.00   50
 14  ω     42.00 107.00   1.00   30.00    --  111.00 -94.00   0.00   65
 15  ω     44.00 125.00   1.00   30.00    --  111.00 -15.00-120.00   81
 16  ω    -53.00 -21.00   1.00    6.00    --  -37.78 -57.00 120.00   32
 17  ω    -88.00 -61.00   1.00    6.00    --  -37.78 -57.00 120.00   27
 18  ω    -69.00 -22.00   1.00    6.00    --  -37.78 -57.00-150.00   47
 19  ω   -104.00 -77.00   1.00    6.00    --  -37.78 -57.00-150.00   27
 20  ω    -97.00 -34.00   1.00    6.00    --  -37.78 178.00-150.00   63
 21  ω      1.00  68.00   1.00    6.00    --   37.78 -99.00  30.00   67
 22  ω    136.00 176.00   1.00   30.00    --  111.00  45.00-180.00   40
 23  ω     95.00 122.00   1.00   30.00    --  111.00 -45.00-180.00   27
 24  ω     51.00 129.00   1.00   30.00    --  111.00 -61.00 120.00   78
 25  ω     71.00 115.00   1.00   30.00    --  111.00-111.00  90.00   44
 26  ω     66.00  93.00   1.00   30.00    --  111.00 -45.00-180.00   27
 27  ω     48.00 132.00   1.00   30.00    --  111.00 -30.00  60.00   84
 28  ω     94.00 108.00   1.00   30.00    --  111.00  61.00  60.00   14
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0607862000
_diffrn_orient_matrix_UB_12      0.0089107000
_diffrn_orient_matrix_UB_13      -0.0049515000
_diffrn_orient_matrix_UB_21      -0.0295666000
_diffrn_orient_matrix_UB_22      -0.0109677000
_diffrn_orient_matrix_UB_23      -0.0523937000
_diffrn_orient_matrix_UB_31      -0.0035520000
_diffrn_orient_matrix_UB_32      0.2416360000
_diffrn_orient_matrix_UB_33      -0.0021720000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5897
_reflns_number_total             8883
_reflns_odcompleteness_completeness 97.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     571
_refine_ls_number_reflns         8883
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.029
_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)+(0.0402P)²+0.1628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1203
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C5(H5), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C10(H10A,H10B), C14(H14A,H14B), C18(H18A,H18B), C3(H3A,H3B), C4(H4A,H4B),
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,
 H14B), C18(H18A,H18B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C14(H14A,H14B), C18(H18A,H18B)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C13(H13A,H13B,H13C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1_1 C 0.23656(11) 0.6685(3) 0.39047(8) 0.0180(5) Uani 1 1 d . . . . .
O2_1 O 0.23939(8) 0.7760(3) 0.35871(6) 0.0223(4) Uani 1 1 d . . . . .
C3_1 C 0.18674(11) 0.6955(4) 0.40828(9) 0.0214(5) Uani 1 1 d . . . . .
H3A_1 H 0.203185 0.694914 0.442101 0.026 Uiso 1 1 calc R . . . .
H3B_1 H 0.160135 0.572983 0.398504 0.026 Uiso 1 1 calc R . . . .
C4_1 C 0.15062(11) 0.8957(4) 0.39248(9) 0.0209(5) Uani 1 1 d . . . . .
H4A_1 H 0.177129 1.018626 0.401758 0.025 Uiso 1 1 calc R . . . .
H4B_1 H 0.133213 0.895249 0.358697 0.025 Uiso 1 1 calc R . . . .
C5_1 C 0.10132(11) 0.9200(4) 0.41195(9) 0.0193(5) Uani 1 1 d . . . . .
H5_1 H 0.118199 0.887347 0.445346 0.023 Uiso 1 1 calc R . . . .
C6_1 C 0.07818(12) 1.1459(4) 0.40695(10) 0.0265(6) Uani 1 1 d . . . . .
H6A_1 H 0.111052 1.242793 0.422342 0.032 Uiso 1 1 calc R . . . .
H6B_1 H 0.062152 1.183694 0.374140 0.032 Uiso 1 1 calc R . . . .
C7_1 C 0.03015(12) 1.1725(4) 0.42767(11) 0.0298(6) Uani 1 1 d . . . . .
H7A_1 H 0.047161 1.149011 0.461077 0.036 Uiso 1 1 calc R . . . .
H7B_1 H 0.014845 1.318048 0.422431 0.036 Uiso 1 1 calc R . . . .
C8_1 C -0.01985(11) 1.0196(4) 0.40676(10) 0.0275(6) Uani 1 1 d . . . . .
H8A_1 H -0.040136 1.055325 0.374155 0.033 Uiso 1 1 calc R . . . .
H8B_1 H -0.048627 1.033086 0.422484 0.033 Uiso 1 1 calc R . . . .
C9_1 C 0.00195(12) 0.7931(4) 0.41054(11) 0.0293(6) Uani 1 1 d . . . . .
H9A_1 H 0.017179 0.750465 0.443074 0.035 Uiso 1 1 calc R . . . .
H9B_1 H -0.031234 0.699227 0.394102 0.035 Uiso 1 1 calc R . . . .
C10_1 C 0.05043(11) 0.7695(4) 0.39039(10) 0.0252(5) Uani 1 1 d . . . . .
H10A_1 H 0.033756 0.795886 0.357069 0.030 Uiso 1 1 calc R . . . .
H10B_1 H 0.065335 0.623438 0.395034 0.030 Uiso 1 1 calc R . . . .
B11_1 B 0.28851(12) 0.5001(4) 0.41426(9) 0.0169(5) Uani 1 1 d . . . . .
N12_1 N 0.30297(9) 0.3389(3) 0.37916(7) 0.0157(4) Uani 1 1 d . . . . .
C13_1 C 0.25324(11) 0.2855(4) 0.33655(8) 0.0203(5) Uani 1 1 d . . . . .
H13A_1 H 0.239800 0.412797 0.318194 0.030 Uiso 1 1 calc GR . . . .
H13B_1 H 0.220845 0.226345 0.344465 0.030 Uiso 1 1 calc GR . . . .
H13C_1 H 0.266364 0.182190 0.318940 0.030 Uiso 1 1 calc GR . . . .
C14_1 C 0.35234(10) 0.4438(3) 0.36998(8) 0.0173(5) Uani 1 1 d . . . . .
H14A_1 H 0.337510 0.538561 0.343237 0.021 Uiso 1 1 calc R . . . .
H14B_1 H 0.379050 0.339046 0.364261 0.021 Uiso 1 1 calc R . . . .
C15_1 C 0.38324(11) 0.5665(3) 0.41303(8) 0.0182(5) Uani 1 1 d . . . . .
O16_1 O 0.43332(8) 0.6266(3) 0.42612(6) 0.0254(4) Uani 1 1 d . . . . .
O17_1 O 0.34579(7) 0.6041(2) 0.43521(6) 0.0190(3) Uani 1 1 d . . . . .
C18_1 C 0.32355(11) 0.1475(3) 0.40888(8) 0.0179(5) Uani 1 1 d . . . . .
H18A_1 H 0.366928 0.146592 0.423156 0.021 Uiso 1 1 calc R . . . .
H18B_1 H 0.310838 0.017493 0.390678 0.021 Uiso 1 1 calc R . . . .
C19_1 C 0.29532(11) 0.1635(4) 0.44515(8) 0.0189(5) Uani 1 1 d . . . . .
O20_1 O 0.29231(8) 0.0226(3) 0.46976(6) 0.0231(4) Uani 1 1 d . . . . .
O21_1 O 0.27496(8) 0.3579(2) 0.44633(6) 0.0190(3) Uani 1 1 d . . . . .
C1_2 C 0.28852(11) 0.7628(4) 0.24023(9) 0.0200(5) Uani 1 1 d . . . . .
O2_2 O 0.29309(8) 0.6345(3) 0.27069(6) 0.0280(4) Uani 1 1 d . . . . .
C3_2 C 0.23571(11) 0.7648(4) 0.19718(8) 0.0219(5) Uani 1 1 d . . . . .
H3A_2 H 0.248274 0.729290 0.171169 0.026 Uiso 1 1 calc R . . . .
H3B_2 H 0.219308 0.908829 0.192110 0.026 Uiso 1 1 calc R . . . .
C4_2 C 0.18729(11) 0.6124(4) 0.19749(9) 0.0238(5) Uani 1 1 d . . . . .
H4A_2 H 0.158198 0.600792 0.166097 0.029 Uiso 1 1 calc R . . . .
H4B_2 H 0.204749 0.471551 0.206699 0.029 Uiso 1 1 calc R . . . .
C5_2 C 0.15552(11) 0.6793(4) 0.22980(9) 0.0209(5) Uani 1 1 d . . . . .
H5_2 H 0.186061 0.721255 0.259514 0.025 Uiso 1 1 calc R . . . .
C6_2 C 0.11479(12) 0.8684(4) 0.21172(9) 0.0246(5) Uani 1 1 d . . . . .
H6A_2 H 0.138083 0.988521 0.207252 0.030 Uiso 1 1 calc R . . . .
H6B_2 H 0.084979 0.832550 0.181683 0.030 Uiso 1 1 calc R . . . .
C7_2 C 0.08396(13) 0.9322(4) 0.24454(10) 0.0285(6) Uani 1 1 d . . . . .
H7A_2 H 0.056181 1.048093 0.230870 0.034 Uiso 1 1 calc R . . . .
H7B_2 H 0.113469 0.984334 0.273318 0.034 Uiso 1 1 calc R . . . .
C8_2 C 0.05047(12) 0.7481(4) 0.25517(10) 0.0285(6) Uani 1 1 d . . . . .
H8A_2 H 0.017620 0.707640 0.227124 0.034 Uiso 1 1 calc R . . . .
H8B_2 H 0.033621 0.791993 0.278359 0.034 Uiso 1 1 calc R . . . .
C9_2 C 0.09075(12) 0.5587(4) 0.27304(9) 0.0266(5) Uani 1 1 d . . . . .
H9A_2 H 0.120996 0.593781 0.302927 0.032 Uiso 1 1 calc R . . . .
H9B_2 H 0.067433 0.438866 0.277606 0.032 Uiso 1 1 calc R . . . .
C10_2 C 0.12067(11) 0.4961(4) 0.23924(9) 0.0237(5) Uani 1 1 d . . . . .
H10A_2 H 0.090500 0.449952 0.210198 0.028 Uiso 1 1 calc R . . . .
H10B_2 H 0.147505 0.376482 0.251865 0.028 Uiso 1 1 calc R . . . .
B11_2 B 0.34280(12) 0.9212(4) 0.24798(10) 0.0185(5) Uani 1 1 d . . . . .
N12_2 N 0.40418(9) 0.7932(3) 0.25809(7) 0.0173(4) Uani 1 1 d . . . . .
C13_2 C 0.39811(11) 0.5841(3) 0.23518(8) 0.0201(5) Uani 1 1 d . . . . .
H13A_2 H 0.437177 0.523694 0.241101 0.030 Uiso 1 1 calc GR . . . .
H13B_2 H 0.378050 0.601456 0.202171 0.030 Uiso 1 1 calc GR . . . .
H13C_2 H 0.375120 0.490087 0.247221 0.030 Uiso 1 1 calc GR . . . .
C14_2 C 0.43697(11) 0.9429(4) 0.23869(9) 0.0209(5) Uani 1 1 d . . . . .
H14A_2 H 0.460884 0.864894 0.224068 0.025 Uiso 1 1 calc R . . . .
H14B_2 H 0.463382 1.033190 0.263100 0.025 Uiso 1 1 calc R . . . .
C15_2 C 0.39082(12) 1.0747(4) 0.20368(9) 0.0213(5) Uani 1 1 d . . . . .
O16_2 O 0.40031(9) 1.1853(3) 0.17582(7) 0.0290(4) Uani 1 1 d . . . . .
O17_2 O 0.33948(8) 1.0579(3) 0.20976(6) 0.0227(4) Uani 1 1 d . . . . .
C18_2 C 0.43044(11) 0.7805(3) 0.30899(8) 0.0177(5) Uani 1 1 d . . . . .
H18A_2 H 0.473501 0.801862 0.319655 0.021 Uiso 1 1 calc R . . . .
H18B_2 H 0.422210 0.642350 0.320025 0.021 Uiso 1 1 calc R . . . .
C19_2 C 0.40072(11) 0.9566(3) 0.32568(8) 0.0196(5) Uani 1 1 d . . . . .
O20_2 O 0.41561(9) 1.0129(3) 0.36494(6) 0.0266(4) Uani 1 1 d . . . . .
O21_2 O 0.35618(8) 1.0380(2) 0.29145(6) 0.0216(4) Uani 1 1 d . . . . .
C1_3 C 0.65528(11) 1.0668(4) 0.39760(8) 0.0185(5) Uani 1 1 d . . . . .
O2_3 O 0.66416(8) 1.2060(3) 0.37366(6) 0.0235(4) Uani 1 1 d . . . . .
C3_3 C 0.69908(11) 0.8953(4) 0.41793(9) 0.0208(5) Uani 1 1 d . . . . .
H3A_3 H 0.678284 0.758860 0.410787 0.025 Uiso 1 1 calc R . . . .
H3B_3 H 0.713926 0.911647 0.451580 0.025 Uiso 1 1 calc R . . . .
C4_3 C 0.75174(11) 0.8858(4) 0.40225(9) 0.0214(5) Uani 1 1 d . . . . .
H4A_3 H 0.776984 1.010094 0.414101 0.026 Uiso 1 1 calc R . . . .
H4B_3 H 0.737668 0.891335 0.368449 0.026 Uiso 1 1 calc R . . . .
C5_3 C 0.78830(11) 0.6860(4) 0.41860(8) 0.0197(5) Uani 1 1 d . . . . .
H5_3 H 0.761135 0.563082 0.408750 0.024 Uiso 1 1 calc R . . . .
C6_3 C 0.83517(11) 0.6636(4) 0.39654(9) 0.0216(5) Uani 1 1 d . . . . .
H6A_3 H 0.816061 0.666514 0.362863 0.026 Uiso 1 1 calc R . . . .
H6B_3 H 0.862669 0.783906 0.405677 0.026 Uiso 1 1 calc R . . . .
C7_3 C 0.86953(11) 0.4584(4) 0.41094(9) 0.0233(5) Uani 1 1 d . . . . .
H7A_3 H 0.842443 0.337697 0.400259 0.028 Uiso 1 1 calc R . . . .
H7B_3 H 0.899708 0.448796 0.396467 0.028 Uiso 1 1 calc R . . . .
C8_3 C 0.89914(12) 0.4478(4) 0.46272(9) 0.0281(6) Uani 1 1 d . . . . .
H8A_3 H 0.929263 0.559571 0.473066 0.034 Uiso 1 1 calc R . . . .
H8B_3 H 0.919071 0.310482 0.471446 0.034 Uiso 1 1 calc R . . . .
C9_3 C 0.85394(12) 0.4755(4) 0.48619(9) 0.0278(6) Uani 1 1 d . . . . .
H9A_3 H 0.874566 0.480858 0.519696 0.033 Uiso 1 1 calc R . . . .
H9B_3 H 0.827281 0.352598 0.479259 0.033 Uiso 1 1 calc R . . . .
C10_3 C 0.81775(12) 0.6753(4) 0.47063(9) 0.0249(5) Uani 1 1 d . . . . .
H10A_3 H 0.843643 0.799055 0.481349 0.030 Uiso 1 1 calc R . . . .
H10B_3 H 0.787164 0.681167 0.484756 0.030 Uiso 1 1 calc R . . . .
B11_3 B 0.59363(12) 1.0643(4) 0.40680(9) 0.0169(5) Uani 1 1 d . . . . .
N12_3 N 0.58163(9) 1.2710(3) 0.43331(7) 0.0158(4) Uani 1 1 d . . . . .
C13_3 C 0.63612(11) 1.3828(3) 0.46230(8) 0.0194(5) Uani 1 1 d . . . . .
H13A_3 H 0.658029 1.430740 0.443130 0.029 Uiso 1 1 calc GR . . . .
H13B_3 H 0.660674 1.286834 0.485793 0.029 Uiso 1 1 calc GR . . . .
H13C_3 H 0.625352 1.504226 0.476985 0.029 Uiso 1 1 calc GR . . . .
C14_3 C 0.54296(10) 1.4075(3) 0.39626(8) 0.0174(5) Uani 1 1 d . . . . .
H14A_3 H 0.565915 1.522092 0.389130 0.021 Uiso 1 1 calc R . . . .
H14B_3 H 0.511408 1.470157 0.405307 0.021 Uiso 1 1 calc R . . . .
C15_3 C 0.51738(10) 1.2638(3) 0.35553(8) 0.0170(5) Uani 1 1 d . . . . .
O16_3 O 0.47902(8) 1.3120(3) 0.31989(6) 0.0212(4) Uani 1 1 d . . . . .
O17_3 O 0.54372(7) 1.0784(2) 0.36263(6) 0.0191(3) Uani 1 1 d . . . . .
C18_3 C 0.55023(11) 1.1772(4) 0.46254(8) 0.0203(5) Uani 1 1 d . . . . .
H18A_3 H 0.507182 1.193861 0.447722 0.024 Uiso 1 1 calc R . . . .
H18B_3 H 0.562870 1.246241 0.492846 0.024 Uiso 1 1 calc R . . . .
C19_3 C 0.56686(11) 0.9466(4) 0.46743(8) 0.0198(5) Uani 1 1 d . . . . .
O20_3 O 0.56234(8) 0.8284(3) 0.49614(6) 0.0263(4) Uani 1 1 d . . . . .
O21_3 O 0.58801(8) 0.8893(2) 0.43495(6) 0.0199(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
C1_1 O2_1 1.227(3) . ?
C1_1 C3_1 1.510(3) . ?
C1_1 B11_1 1.624(3) . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C3_1 C4_1 1.528(3) . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4B_1 0.9900 . ?
C4_1 C5_1 1.531(3) . ?
C5_1 H5_1 1.0000 . ?
C5_1 C6_1 1.532(3) . ?
C5_1 C10_1 1.521(3) . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
C6_1 C7_1 1.531(3) . ?
C7_1 H7A_1 0.9900 . ?
C7_1 H7B_1 0.9900 . ?
C7_1 C8_1 1.514(4) . ?
C8_1 H8A_1 0.9900 . ?
C8_1 H8B_1 0.9900 . ?
C8_1 C9_1 1.526(3) . ?
C9_1 H9A_1 0.9900 . ?
C9_1 H9B_1 0.9900 . ?
C9_1 C10_1 1.527(3) . ?
C10_1 H10A_1 0.9900 . ?
C10_1 H10B_1 0.9900 . ?
B11_1 N12_1 1.628(3) . ?
B11_1 O17_1 1.471(3) . ?
B11_1 O21_1 1.471(3) . ?
N12_1 C13_1 1.489(3) . ?
N12_1 C14_1 1.487(3) . ?
N12_1 C18_1 1.507(3) . ?
C13_1 H13A_1 0.9800 . ?
C13_1 H13B_1 0.9800 . ?
C13_1 H13C_1 0.9800 . ?
C14_1 H14A_1 0.9900 . ?
C14_1 H14B_1 0.9900 . ?
C14_1 C15_1 1.508(3) . ?
C15_1 O16_1 1.202(3) . ?
C15_1 O17_1 1.346(3) . ?
C18_1 H18A_1 0.9900 . ?
C18_1 H18B_1 0.9900 . ?
C18_1 C19_1 1.521(3) . ?
C19_1 O20_1 1.200(3) . ?
C19_1 O21_1 1.338(3) . ?
C1_2 O2_2 1.229(3) . ?
C1_2 C3_2 1.498(4) . ?
C1_2 B11_2 1.610(3) . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3B_2 0.9900 . ?
C3_2 C4_2 1.528(3) . ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4B_2 0.9900 . ?
C4_2 C5_2 1.532(3) . ?
C5_2 H5_2 1.0000 . ?
C5_2 C6_2 1.534(3) . ?
C5_2 C10_2 1.530(3) . ?
C6_2 H6A_2 0.9900 . ?
C6_2 H6B_2 0.9900 . ?
C6_2 C7_2 1.523(3) . ?
C7_2 H7A_2 0.9900 . ?
C7_2 H7B_2 0.9900 . ?
C7_2 C8_2 1.529(3) . ?
C8_2 H8A_2 0.9900 . ?
C8_2 H8B_2 0.9900 . ?
C8_2 C9_2 1.529(4) . ?
C9_2 H9A_2 0.9900 . ?
C9_2 H9B_2 0.9900 . ?
C9_2 C10_2 1.531(3) . ?
C10_2 H10A_2 0.9900 . ?
C10_2 H10B_2 0.9900 . ?
B11_2 N12_2 1.631(3) . ?
B11_2 O17_2 1.457(3) . ?
B11_2 O21_2 1.481(3) . ?
N12_2 C13_2 1.493(3) . ?
N12_2 C14_2 1.500(3) . ?
N12_2 C18_2 1.494(3) . ?
C13_2 H13A_2 0.9800 . ?
C13_2 H13B_2 0.9800 . ?
C13_2 H13C_2 0.9800 . ?
C14_2 H14A_2 0.9900 . ?
C14_2 H14B_2 0.9900 . ?
C14_2 C15_2 1.515(4) . ?
C15_2 O16_2 1.204(3) . ?
C15_2 O17_2 1.331(3) . ?
C18_2 H18A_2 0.9900 . ?
C18_2 H18B_2 0.9900 . ?
C18_2 C19_2 1.522(3) . ?
C19_2 O20_2 1.205(3) . ?
C19_2 O21_2 1.330(3) . ?
C1_3 O2_3 1.227(3) . ?
C1_3 C3_3 1.501(3) . ?
C1_3 B11_3 1.622(3) . ?
C3_3 H3A_3 0.9900 . ?
C3_3 H3B_3 0.9900 . ?
C3_3 C4_3 1.525(3) . ?
C4_3 H4A_3 0.9900 . ?
C4_3 H4B_3 0.9900 . ?
C4_3 C5_3 1.532(3) . ?
C5_3 H5_3 1.0000 . ?
C5_3 C6_3 1.532(3) . ?
C5_3 C10_3 1.531(3) . ?
C6_3 H6A_3 0.9900 . ?
C6_3 H6B_3 0.9900 . ?
C6_3 C7_3 1.531(3) . ?
C7_3 H7A_3 0.9900 . ?
C7_3 H7B_3 0.9900 . ?
C7_3 C8_3 1.524(4) . ?
C8_3 H8A_3 0.9900 . ?
C8_3 H8B_3 0.9900 . ?
C8_3 C9_3 1.531(3) . ?
C9_3 H9A_3 0.9900 . ?
C9_3 H9B_3 0.9900 . ?
C9_3 C10_3 1.526(3) . ?
C10_3 H10A_3 0.9900 . ?
C10_3 H10B_3 0.9900 . ?
B11_3 N12_3 1.635(3) . ?
B11_3 O17_3 1.486(3) . ?
B11_3 O21_3 1.456(3) . ?
N12_3 C13_3 1.496(3) . ?
N12_3 C14_3 1.488(3) . ?
N12_3 C18_3 1.505(3) . ?
C13_3 H13A_3 0.9800 . ?
C13_3 H13B_3 0.9800 . ?
C13_3 H13C_3 0.9800 . ?
C14_3 H14A_3 0.9900 . ?
C14_3 H14B_3 0.9900 . ?
C14_3 C15_3 1.512(3) . ?
C15_3 O16_3 1.214(3) . ?
C15_3 O17_3 1.324(3) . ?
C18_3 H18A_3 0.9900 . ?
C18_3 H18B_3 0.9900 . ?
C18_3 C19_3 1.515(3) . ?
C19_3 O20_3 1.206(3) . ?
C19_3 O21_3 1.340(3) . ?

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
O2_1 C1_1 C3_1 121.0(2) . . ?
O2_1 C1_1 B11_1 118.9(2) . . ?
C3_1 C1_1 B11_1 120.09(19) . . ?
C1_1 C3_1 H3A_1 108.6 . . ?
C1_1 C3_1 H3B_1 108.6 . . ?
C1_1 C3_1 C4_1 114.82(19) . . ?
H3A_1 C3_1 H3B_1 107.5 . . ?
C4_1 C3_1 H3A_1 108.6 . . ?
C4_1 C3_1 H3B_1 108.6 . . ?
C3_1 C4_1 H4A_1 108.9 . . ?
C3_1 C4_1 H4B_1 108.9 . . ?
H4A_1 C4_1 H4B_1 107.7 . . ?
C5_1 C4_1 C3_1 113.40(19) . . ?
C5_1 C4_1 H4A_1 108.9 . . ?
C5_1 C4_1 H4B_1 108.9 . . ?
C4_1 C5_1 H5_1 107.6 . . ?
C4_1 C5_1 C6_1 111.41(19) . . ?
C4_1 C5_1 C10_1 112.9(2) . . ?
C6_1 C5_1 H5_1 107.6 . . ?
C10_1 C5_1 H5_1 107.6 . . ?
C10_1 C5_1 C6_1 109.5(2) . . ?
C5_1 C6_1 H6A_1 109.3 . . ?
C5_1 C6_1 H6B_1 109.3 . . ?
H6A_1 C6_1 H6B_1 108.0 . . ?
C7_1 C6_1 C5_1 111.6(2) . . ?
C7_1 C6_1 H6A_1 109.3 . . ?
C7_1 C6_1 H6B_1 109.3 . . ?
C6_1 C7_1 H7A_1 109.4 . . ?
C6_1 C7_1 H7B_1 109.4 . . ?
H7A_1 C7_1 H7B_1 108.0 . . ?
C8_1 C7_1 C6_1 111.2(2) . . ?
C8_1 C7_1 H7A_1 109.4 . . ?
C8_1 C7_1 H7B_1 109.4 . . ?
C7_1 C8_1 H8A_1 109.3 . . ?
C7_1 C8_1 H8B_1 109.3 . . ?
C7_1 C8_1 C9_1 111.7(2) . . ?
H8A_1 C8_1 H8B_1 107.9 . . ?
C9_1 C8_1 H8A_1 109.3 . . ?
C9_1 C8_1 H8B_1 109.3 . . ?
C8_1 C9_1 H9A_1 109.4 . . ?
C8_1 C9_1 H9B_1 109.4 . . ?
H9A_1 C9_1 H9B_1 108.0 . . ?
C10_1 C9_1 C8_1 111.0(2) . . ?
C10_1 C9_1 H9A_1 109.4 . . ?
C10_1 C9_1 H9B_1 109.4 . . ?
C5_1 C10_1 H10A_1 109.1 . . ?
C5_1 C10_1 H10B_1 109.1 . . ?
C9_1 C10_1 C5_1 112.4(2) . . ?
C9_1 C10_1 H10A_1 109.1 . . ?
C9_1 C10_1 H10B_1 109.1 . . ?
H10A_1 C10_1 H10B_1 107.9 . . ?
C1_1 B11_1 N12_1 115.1(2) . . ?
O17_1 B11_1 C1_1 111.62(19) . . ?
O17_1 B11_1 N12_1 100.87(17) . . ?
O21_1 B11_1 C1_1 113.19(19) . . ?
O21_1 B11_1 N12_1 103.00(17) . . ?
O21_1 B11_1 O17_1 112.2(2) . . ?
C13_1 N12_1 B11_1 116.55(18) . . ?
C13_1 N12_1 C18_1 110.84(18) . . ?
C14_1 N12_1 B11_1 103.15(17) . . ?
C14_1 N12_1 C13_1 112.72(17) . . ?
C14_1 N12_1 C18_1 111.50(18) . . ?
C18_1 N12_1 B11_1 101.38(16) . . ?
N12_1 C13_1 H13A_1 109.5 . . ?
N12_1 C13_1 H13B_1 109.5 . . ?
N12_1 C13_1 H13C_1 109.5 . . ?
H13A_1 C13_1 H13B_1 109.5 . . ?
H13A_1 C13_1 H13C_1 109.5 . . ?
H13B_1 C13_1 H13C_1 109.5 . . ?
N12_1 C14_1 H14A_1 110.9 . . ?
N12_1 C14_1 H14B_1 110.9 . . ?
N12_1 C14_1 C15_1 104.05(17) . . ?
H14A_1 C14_1 H14B_1 109.0 . . ?
C15_1 C14_1 H14A_1 110.9 . . ?
C15_1 C14_1 H14B_1 110.9 . . ?
O16_1 C15_1 C14_1 126.5(2) . . ?
O16_1 C15_1 O17_1 123.7(2) . . ?
O17_1 C15_1 C14_1 109.7(2) . . ?
C15_1 O17_1 B11_1 113.35(18) . . ?
N12_1 C18_1 H18A_1 110.7 . . ?
N12_1 C18_1 H18B_1 110.7 . . ?
N12_1 C18_1 C19_1 105.45(17) . . ?
H18A_1 C18_1 H18B_1 108.8 . . ?
C19_1 C18_1 H18A_1 110.7 . . ?
C19_1 C18_1 H18B_1 110.7 . . ?
O20_1 C19_1 C18_1 125.0(2) . . ?
O20_1 C19_1 O21_1 124.5(2) . . ?
O21_1 C19_1 C18_1 110.52(19) . . ?
C19_1 O21_1 B11_1 112.11(17) . . ?
O2_2 C1_2 C3_2 121.1(2) . . ?
O2_2 C1_2 B11_2 117.0(2) . . ?
C3_2 C1_2 B11_2 121.9(2) . . ?
C1_2 C3_2 H3A_2 108.7 . . ?
C1_2 C3_2 H3B_2 108.7 . . ?
C1_2 C3_2 C4_2 114.1(2) . . ?
H3A_2 C3_2 H3B_2 107.6 . . ?
C4_2 C3_2 H3A_2 108.7 . . ?
C4_2 C3_2 H3B_2 108.7 . . ?
C3_2 C4_2 H4A_2 108.9 . . ?
C3_2 C4_2 H4B_2 108.9 . . ?
H4A_2 C4_2 H4B_2 107.7 . . ?
C5_2 C4_2 C3_2 113.3(2) . . ?
C5_2 C4_2 H4A_2 108.9 . . ?
C5_2 C4_2 H4B_2 108.9 . . ?
C4_2 C5_2 H5_2 107.7 . . ?
C4_2 C5_2 C6_2 112.6(2) . . ?
C4_2 C5_2 C10_2 110.9(2) . . ?
C6_2 C5_2 H5_2 107.7 . . ?
C10_2 C5_2 H5_2 107.7 . . ?
C10_2 C5_2 C6_2 109.8(2) . . ?
C5_2 C6_2 H6A_2 109.3 . . ?
C5_2 C6_2 H6B_2 109.3 . . ?
H6A_2 C6_2 H6B_2 108.0 . . ?
C7_2 C6_2 C5_2 111.6(2) . . ?
C7_2 C6_2 H6A_2 109.3 . . ?
C7_2 C6_2 H6B_2 109.3 . . ?
C6_2 C7_2 H7A_2 109.3 . . ?
C6_2 C7_2 H7B_2 109.3 . . ?
C6_2 C7_2 C8_2 111.6(2) . . ?
H7A_2 C7_2 H7B_2 108.0 . . ?
C8_2 C7_2 H7A_2 109.3 . . ?
C8_2 C7_2 H7B_2 109.3 . . ?
C7_2 C8_2 H8A_2 109.4 . . ?
C7_2 C8_2 H8B_2 109.4 . . ?
C7_2 C8_2 C9_2 111.2(2) . . ?
H8A_2 C8_2 H8B_2 108.0 . . ?
C9_2 C8_2 H8A_2 109.4 . . ?
C9_2 C8_2 H8B_2 109.4 . . ?
C8_2 C9_2 H9A_2 109.5 . . ?
C8_2 C9_2 H9B_2 109.5 . . ?
H9A_2 C9_2 H9B_2 108.1 . . ?
C10_2 C9_2 C8_2 110.6(2) . . ?
C10_2 C9_2 H9A_2 109.5 . . ?
C10_2 C9_2 H9B_2 109.5 . . ?
C5_2 C10_2 H10A_2 109.3 . . ?
C5_2 C10_2 H10B_2 109.3 . . ?
C9_2 C10_2 C5_2 111.4(2) . . ?
C9_2 C10_2 H10A_2 109.3 . . ?
C9_2 C10_2 H10B_2 109.3 . . ?
H10A_2 C10_2 H10B_2 108.0 . . ?
C1_2 B11_2 N12_2 111.20(19) . . ?
O17_2 B11_2 C1_2 116.4(2) . . ?
O17_2 B11_2 N12_2 103.91(17) . . ?
O17_2 B11_2 O21_2 112.57(19) . . ?
O21_2 B11_2 C1_2 110.86(18) . . ?
O21_2 B11_2 N12_2 100.51(19) . . ?
C13_2 N12_2 B11_2 115.03(19) . . ?
C13_2 N12_2 C14_2 110.42(17) . . ?
C13_2 N12_2 C18_2 113.32(18) . . ?
C14_2 N12_2 B11_2 100.61(17) . . ?
C18_2 N12_2 B11_2 104.62(17) . . ?
C18_2 N12_2 C14_2 112.10(19) . . ?
N12_2 C13_2 H13A_2 109.5 . . ?
N12_2 C13_2 H13B_2 109.5 . . ?
N12_2 C13_2 H13C_2 109.5 . . ?
H13A_2 C13_2 H13B_2 109.5 . . ?
H13A_2 C13_2 H13C_2 109.5 . . ?
H13B_2 C13_2 H13C_2 109.5 . . ?
N12_2 C14_2 H14A_2 110.5 . . ?
N12_2 C14_2 H14B_2 110.5 . . ?
N12_2 C14_2 C15_2 106.25(19) . . ?
H14A_2 C14_2 H14B_2 108.7 . . ?
C15_2 C14_2 H14A_2 110.5 . . ?
C15_2 C14_2 H14B_2 110.5 . . ?
O16_2 C15_2 C14_2 124.4(2) . . ?
O16_2 C15_2 O17_2 125.3(3) . . ?
O17_2 C15_2 C14_2 110.23(19) . . ?
C15_2 O17_2 B11_2 112.36(19) . . ?
N12_2 C18_2 H18A_2 110.9 . . ?
N12_2 C18_2 H18B_2 110.9 . . ?
N12_2 C18_2 C19_2 104.41(19) . . ?
H18A_2 C18_2 H18B_2 108.9 . . ?
C19_2 C18_2 H18A_2 110.9 . . ?
C19_2 C18_2 H18B_2 110.9 . . ?
O20_2 C19_2 C18_2 124.0(2) . . ?
O20_2 C19_2 O21_2 124.8(2) . . ?
O21_2 C19_2 C18_2 111.2(2) . . ?
C19_2 O21_2 B11_2 113.37(18) . . ?
O2_3 C1_3 C3_3 122.2(2) . . ?
O2_3 C1_3 B11_3 119.1(2) . . ?
C3_3 C1_3 B11_3 118.67(19) . . ?
C1_3 C3_3 H3A_3 108.2 . . ?
C1_3 C3_3 H3B_3 108.2 . . ?
C1_3 C3_3 C4_3 116.3(2) . . ?
H3A_3 C3_3 H3B_3 107.4 . . ?
C4_3 C3_3 H3A_3 108.2 . . ?
C4_3 C3_3 H3B_3 108.2 . . ?
C3_3 C4_3 H4A_3 109.1 . . ?
C3_3 C4_3 H4B_3 109.1 . . ?
C3_3 C4_3 C5_3 112.32(19) . . ?
H4A_3 C4_3 H4B_3 107.9 . . ?
C5_3 C4_3 H4A_3 109.1 . . ?
C5_3 C4_3 H4B_3 109.1 . . ?
C4_3 C5_3 H5_3 107.7 . . ?
C4_3 C5_3 C6_3 111.28(19) . . ?
C4_3 C5_3 C10_3 113.0(2) . . ?
C6_3 C5_3 H5_3 107.7 . . ?
C6_3 C5_3 C10_3 109.3(2) . . ?
C10_3 C5_3 H5_3 107.7 . . ?
C5_3 C6_3 H6A_3 109.4 . . ?
C5_3 C6_3 H6B_3 109.4 . . ?
H6A_3 C6_3 H6B_3 108.0 . . ?
C7_3 C6_3 C5_3 111.24(19) . . ?
C7_3 C6_3 H6A_3 109.4 . . ?
C7_3 C6_3 H6B_3 109.4 . . ?
C6_3 C7_3 H7A_3 109.5 . . ?
C6_3 C7_3 H7B_3 109.5 . . ?
H7A_3 C7_3 H7B_3 108.1 . . ?
C8_3 C7_3 C6_3 110.8(2) . . ?
C8_3 C7_3 H7A_3 109.5 . . ?
C8_3 C7_3 H7B_3 109.5 . . ?
C7_3 C8_3 H8A_3 109.5 . . ?
C7_3 C8_3 H8B_3 109.5 . . ?
C7_3 C8_3 C9_3 110.7(2) . . ?
H8A_3 C8_3 H8B_3 108.1 . . ?
C9_3 C8_3 H8A_3 109.5 . . ?
C9_3 C8_3 H8B_3 109.5 . . ?
C8_3 C9_3 H9A_3 109.2 . . ?
C8_3 C9_3 H9B_3 109.2 . . ?
C8_3 C9_3 C10_3 112.0(2) . . ?
H9A_3 C9_3 H9B_3 107.9 . . ?
C10_3 C9_3 H9A_3 109.2 . . ?
C10_3 C9_3 H9B_3 109.2 . . ?
C5_3 C10_3 H10A_3 109.2 . . ?
C5_3 C10_3 H10B_3 109.2 . . ?
C9_3 C10_3 C5_3 112.2(2) . . ?
C9_3 C10_3 H10A_3 109.2 . . ?
C9_3 C10_3 H10B_3 109.2 . . ?
H10A_3 C10_3 H10B_3 107.9 . . ?
C1_3 B11_3 N12_3 115.00(19) . . ?
O17_3 B11_3 C1_3 109.75(18) . . ?
O17_3 B11_3 N12_3 100.94(18) . . ?
O21_3 B11_3 C1_3 113.8(2) . . ?
O21_3 B11_3 N12_3 103.78(17) . . ?
O21_3 B11_3 O17_3 112.8(2) . . ?
C13_3 N12_3 B11_3 114.34(18) . . ?
C13_3 N12_3 C18_3 110.55(18) . . ?
C14_3 N12_3 B11_3 104.58(17) . . ?
C14_3 N12_3 C13_3 112.09(17) . . ?
C14_3 N12_3 C18_3 112.82(18) . . ?
C18_3 N12_3 B11_3 101.97(16) . . ?
N12_3 C13_3 H13A_3 109.5 . . ?
N12_3 C13_3 H13B_3 109.5 . . ?
N12_3 C13_3 H13C_3 109.5 . . ?
H13A_3 C13_3 H13B_3 109.5 . . ?
H13A_3 C13_3 H13C_3 109.5 . . ?
H13B_3 C13_3 H13C_3 109.5 . . ?
N12_3 C14_3 H14A_3 110.7 . . ?
N12_3 C14_3 H14B_3 110.7 . . ?
N12_3 C14_3 C15_3 105.21(17) . . ?
H14A_3 C14_3 H14B_3 108.8 . . ?
C15_3 C14_3 H14A_3 110.7 . . ?
C15_3 C14_3 H14B_3 110.7 . . ?
O16_3 C15_3 C14_3 125.1(2) . . ?
O16_3 C15_3 O17_3 123.3(2) . . ?
O17_3 C15_3 C14_3 111.5(2) . . ?
C15_3 O17_3 B11_3 113.45(18) . . ?
N12_3 C18_3 H18A_3 110.6 . . ?
N12_3 C18_3 H18B_3 110.6 . . ?
N12_3 C18_3 C19_3 105.74(17) . . ?
H18A_3 C18_3 H18B_3 108.7 . . ?
C19_3 C18_3 H18A_3 110.6 . . ?
C19_3 C18_3 H18B_3 110.6 . . ?
O20_3 C19_3 C18_3 126.0(2) . . ?
O20_3 C19_3 O21_3 123.6(2) . . ?
O21_3 C19_3 C18_3 110.32(19) . . ?
C19_3 O21_3 B11_3 113.08(18) . . ?

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
C1_1 C3_1 C4_1 C5_1 -178.8(2) . . . . ?
C1_1 B11_1 N12_1 C13_1 -29.6(3) . . . . ?
C1_1 B11_1 N12_1 C14_1 94.5(2) . . . . ?
C1_1 B11_1 N12_1 C18_1 -149.98(19) . . . . ?
C1_1 B11_1 O17_1 C15_1 -110.1(2) . . . . ?
C1_1 B11_1 O21_1 C19_1 143.6(2) . . . . ?
O2_1 C1_1 C3_1 C4_1 -14.4(3) . . . . ?
O2_1 C1_1 B11_1 N12_1 -52.2(3) . . . . ?
O2_1 C1_1 B11_1 O17_1 62.0(3) . . . . ?
O2_1 C1_1 B11_1 O21_1 -170.3(2) . . . . ?
C3_1 C1_1 B11_1 N12_1 129.5(2) . . . . ?
C3_1 C1_1 B11_1 O17_1 -116.3(2) . . . . ?
C3_1 C1_1 B11_1 O21_1 11.4(3) . . . . ?
C3_1 C4_1 C5_1 C6_1 163.6(2) . . . . ?
C3_1 C4_1 C5_1 C10_1 -72.7(3) . . . . ?
C4_1 C5_1 C6_1 C7_1 -178.3(2) . . . . ?
C4_1 C5_1 C10_1 C9_1 179.2(2) . . . . ?
C5_1 C6_1 C7_1 C8_1 -56.2(3) . . . . ?
C6_1 C5_1 C10_1 C9_1 -56.1(3) . . . . ?
C6_1 C7_1 C8_1 C9_1 54.6(3) . . . . ?
C7_1 C8_1 C9_1 C10_1 -54.0(3) . . . . ?
C8_1 C9_1 C10_1 C5_1 55.4(3) . . . . ?
C10_1 C5_1 C6_1 C7_1 56.2(3) . . . . ?
B11_1 C1_1 C3_1 C4_1 163.9(2) . . . . ?
B11_1 N12_1 C14_1 C15_1 29.2(2) . . . . ?
B11_1 N12_1 C18_1 C19_1 24.8(2) . . . . ?
N12_1 B11_1 O17_1 C15_1 12.7(2) . . . . ?
N12_1 B11_1 O21_1 C19_1 18.6(3) . . . . ?
N12_1 C14_1 C15_1 O16_1 157.9(2) . . . . ?
N12_1 C14_1 C15_1 O17_1 -23.2(2) . . . . ?
N12_1 C18_1 C19_1 O20_1 165.4(2) . . . . ?
N12_1 C18_1 C19_1 O21_1 -15.5(3) . . . . ?
C13_1 N12_1 C14_1 C15_1 155.69(18) . . . . ?
C13_1 N12_1 C18_1 C19_1 -99.6(2) . . . . ?
C14_1 N12_1 C18_1 C19_1 133.96(19) . . . . ?
C14_1 C15_1 O17_1 B11_1 5.6(3) . . . . ?
O16_1 C15_1 O17_1 B11_1 -175.5(2) . . . . ?
O17_1 B11_1 N12_1 C13_1 -149.87(18) . . . . ?
O17_1 B11_1 N12_1 C14_1 -25.8(2) . . . . ?
O17_1 B11_1 N12_1 C18_1 89.72(19) . . . . ?
O17_1 B11_1 O21_1 C19_1 -89.0(2) . . . . ?
C18_1 N12_1 C14_1 C15_1 -78.9(2) . . . . ?
C18_1 C19_1 O21_1 B11_1 -3.0(3) . . . . ?
O20_1 C19_1 O21_1 B11_1 176.1(3) . . . . ?
O21_1 B11_1 N12_1 C13_1 94.1(2) . . . . ?
O21_1 B11_1 N12_1 C14_1 -141.82(19) . . . . ?
O21_1 B11_1 N12_1 C18_1 -26.3(2) . . . . ?
O21_1 B11_1 O17_1 C15_1 121.7(2) . . . . ?
C1_2 C3_2 C4_2 C5_2 70.5(3) . . . . ?
C1_2 B11_2 N12_2 C13_2 31.4(3) . . . . ?
C1_2 B11_2 N12_2 C14_2 150.1(2) . . . . ?
C1_2 B11_2 N12_2 C18_2 -93.5(2) . . . . ?
C1_2 B11_2 O17_2 C15_2 -138.4(2) . . . . ?
C1_2 B11_2 O21_2 C19_2 98.6(2) . . . . ?
O2_2 C1_2 C3_2 C4_2 6.1(3) . . . . ?
O2_2 C1_2 B11_2 N12_2 55.3(3) . . . . ?
O2_2 C1_2 B11_2 O17_2 174.0(2) . . . . ?
O2_2 C1_2 B11_2 O21_2 -55.7(3) . . . . ?
C3_2 C1_2 B11_2 N12_2 -122.4(2) . . . . ?
C3_2 C1_2 B11_2 O17_2 -3.7(3) . . . . ?
C3_2 C1_2 B11_2 O21_2 126.7(2) . . . . ?
C3_2 C4_2 C5_2 C6_2 72.6(3) . . . . ?
C3_2 C4_2 C5_2 C10_2 -163.8(2) . . . . ?
C4_2 C5_2 C6_2 C7_2 -179.8(2) . . . . ?
C4_2 C5_2 C10_2 C9_2 177.7(2) . . . . ?
C5_2 C6_2 C7_2 C8_2 -55.3(3) . . . . ?
C6_2 C5_2 C10_2 C9_2 -57.1(3) . . . . ?
C6_2 C7_2 C8_2 C9_2 54.7(3) . . . . ?
C7_2 C8_2 C9_2 C10_2 -55.3(3) . . . . ?
C8_2 C9_2 C10_2 C5_2 57.2(3) . . . . ?
C10_2 C5_2 C6_2 C7_2 56.0(3) . . . . ?
B11_2 C1_2 C3_2 C4_2 -176.4(2) . . . . ?
B11_2 N12_2 C14_2 C15_2 -23.9(2) . . . . ?
B11_2 N12_2 C18_2 C19_2 -20.7(2) . . . . ?
N12_2 B11_2 O17_2 C15_2 -15.8(3) . . . . ?
N12_2 B11_2 O21_2 C19_2 -19.1(2) . . . . ?
N12_2 C14_2 C15_2 O16_2 -166.4(2) . . . . ?
N12_2 C14_2 C15_2 O17_2 16.6(3) . . . . ?
N12_2 C18_2 C19_2 O20_2 -170.6(2) . . . . ?
N12_2 C18_2 C19_2 O21_2 10.0(2) . . . . ?
C13_2 N12_2 C14_2 C15_2 98.0(2) . . . . ?
C13_2 N12_2 C18_2 C19_2 -146.71(18) . . . . ?
C14_2 N12_2 C18_2 C19_2 87.5(2) . . . . ?
C14_2 C15_2 O17_2 B11_2 0.5(3) . . . . ?
O16_2 C15_2 O17_2 B11_2 -176.5(2) . . . . ?
O17_2 B11_2 N12_2 C13_2 -94.5(2) . . . . ?
O17_2 B11_2 N12_2 C14_2 24.1(2) . . . . ?
O17_2 B11_2 N12_2 C18_2 140.51(19) . . . . ?
O17_2 B11_2 O21_2 C19_2 -129.1(2) . . . . ?
C18_2 N12_2 C14_2 C15_2 -134.58(19) . . . . ?
C18_2 C19_2 O21_2 B11_2 6.9(3) . . . . ?
O20_2 C19_2 O21_2 B11_2 -172.5(2) . . . . ?
O21_2 B11_2 N12_2 C13_2 148.86(18) . . . . ?
O21_2 B11_2 N12_2 C14_2 -92.51(19) . . . . ?
O21_2 B11_2 N12_2 C18_2 23.9(2) . . . . ?
O21_2 B11_2 O17_2 C15_2 92.0(2) . . . . ?
C1_3 C3_3 C4_3 C5_3 -170.6(2) . . . . ?
C1_3 B11_3 N12_3 C13_3 -25.1(3) . . . . ?
C1_3 B11_3 N12_3 C14_3 97.9(2) . . . . ?
C1_3 B11_3 N12_3 C18_3 -144.4(2) . . . . ?
C1_3 B11_3 O17_3 C15_3 -106.8(2) . . . . ?
C1_3 B11_3 O21_3 C19_3 135.3(2) . . . . ?
O2_3 C1_3 C3_3 C4_3 -7.8(4) . . . . ?
O2_3 C1_3 B11_3 N12_3 -61.6(3) . . . . ?
O2_3 C1_3 B11_3 O17_3 51.4(3) . . . . ?
O2_3 C1_3 B11_3 O21_3 178.9(2) . . . . ?
C3_3 C1_3 B11_3 N12_3 119.7(2) . . . . ?
C3_3 C1_3 B11_3 O17_3 -127.3(2) . . . . ?
C3_3 C1_3 B11_3 O21_3 0.2(3) . . . . ?
C3_3 C4_3 C5_3 C6_3 171.4(2) . . . . ?
C3_3 C4_3 C5_3 C10_3 -65.2(3) . . . . ?
C4_3 C5_3 C6_3 C7_3 -177.0(2) . . . . ?
C4_3 C5_3 C10_3 C9_3 -180.0(2) . . . . ?
C5_3 C6_3 C7_3 C8_3 -58.6(3) . . . . ?
C6_3 C5_3 C10_3 C9_3 -55.5(3) . . . . ?
C6_3 C7_3 C8_3 C9_3 55.8(3) . . . . ?
C7_3 C8_3 C9_3 C10_3 -53.9(3) . . . . ?
C8_3 C9_3 C10_3 C5_3 54.5(3) . . . . ?
C10_3 C5_3 C6_3 C7_3 57.5(3) . . . . ?
B11_3 C1_3 C3_3 C4_3 170.8(2) . . . . ?
B11_3 N12_3 C14_3 C15_3 18.5(2) . . . . ?
B11_3 N12_3 C18_3 C19_3 22.0(2) . . . . ?
N12_3 B11_3 O17_3 C15_3 15.0(2) . . . . ?
N12_3 B11_3 O21_3 C19_3 9.6(3) . . . . ?
N12_3 C14_3 C15_3 O16_3 172.2(2) . . . . ?
N12_3 C14_3 C15_3 O17_3 -10.4(2) . . . . ?
N12_3 C18_3 C19_3 O20_3 161.7(2) . . . . ?
N12_3 C18_3 C19_3 O21_3 -18.1(3) . . . . ?
C13_3 N12_3 C14_3 C15_3 142.93(18) . . . . ?
C13_3 N12_3 C18_3 C19_3 -100.0(2) . . . . ?
C14_3 N12_3 C18_3 C19_3 133.6(2) . . . . ?
C14_3 C15_3 O17_3 B11_3 -3.9(2) . . . . ?
O16_3 C15_3 O17_3 B11_3 173.6(2) . . . . ?
O17_3 B11_3 N12_3 C13_3 -143.13(18) . . . . ?
O17_3 B11_3 N12_3 C14_3 -20.2(2) . . . . ?
O17_3 B11_3 N12_3 C18_3 97.54(19) . . . . ?
O17_3 B11_3 O21_3 C19_3 -98.8(2) . . . . ?
C18_3 N12_3 C14_3 C15_3 -91.5(2) . . . . ?
C18_3 C19_3 O21_3 B11_3 4.7(3) . . . . ?
O20_3 C19_3 O21_3 B11_3 -175.1(2) . . . . ?
O21_3 B11_3 N12_3 C13_3 99.8(2) . . . . ?
O21_3 B11_3 N12_3 C14_3 -137.19(19) . . . . ?
O21_3 B11_3 N12_3 C18_3 -19.5(2) . . . . ?
O21_3 B11_3 O17_3 C15_3 125.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.932
_oxdiff_exptl_absorpt_empirical_full_min 0.772
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_lucia3
_database_code_depnum_ccdc_archive 'CCDC 1880525'
loop_
_audit_author_name
_audit_author_address
'Daniel Paley'
;Columbia University
United States of America
;
_audit_update_record             
;
2018-11-21 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H12 B N O5'
_chemical_formula_sum            'C9 H12 B N O5'
_chemical_formula_weight         225.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H12 B O5 N'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3672(3)
_cell_length_b                   10.8231(3)
_cell_length_c                   10.9398(4)
_cell_angle_alpha                78.441(3)
_cell_angle_beta                 85.514(3)
_cell_angle_gamma                63.232(3)
_cell_volume                     1073.63(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5697
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      72.7220
_cell_measurement_theta_min      4.1251
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.493
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
7 3 1 0.1177
2 -5 1 0.0991
-6 -6 0 0.0406
3 7 0 0.0807
5 2 5 0.0738
0 0 7 0.1008
-7 -3 1 0.1087
0 0 -7 0.0722
2 7 2 0.0798
0 -6 -3 0.1007

_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.156
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
6.7206 2.8588 0.6172 -0.0218 0.0072 0.9997
1.7857 -4.9288 0.9542 0.8878 -0.3144 0.3360
-5.6678 -5.8956 -0.0364 0.5658 -0.1999 -0.8000
3.1940 6.7716 -0.4587 -0.8607 0.3044 0.4081
4.6700 1.8440 5.3054 -0.0184 -0.7004 0.7135
0.1495 -0.0073 6.9503 -0.0260 -0.9985 0.0475
-6.6086 -2.6905 0.7705 -0.0049 -0.2006 -0.9797
-0.1229 0.0181 -6.9491 0.0260 0.9987 -0.0435
2.0000 7.0000 2.0000 -0.9866 -0.0394 0.2308
-0.0000 -6.0000 -3.0000 0.9628 0.2169 0.0608

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11143
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.887
_diffrn_reflns_theta_min         4.125
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00   1.00   1.00    1.00    --  -64.00  77.00 150.00   89
  2  ω      3.00  92.00   1.00    1.00    --   67.35 -77.00-120.00   89
  3  ω      3.00  92.00   1.00    1.00    --   67.35 -19.00   0.00   89
  4  ω     51.00 135.00   1.00    1.00    --   67.35  57.00   0.00   84
  5  ω    -93.00 -67.00   1.00    1.00    --  -37.78 178.00  90.00   26
  6  ω   -106.00 -71.00   1.00    1.00    --  -37.78-178.00 -90.00   35
  7  ω   -105.00 -73.00   1.00    1.00    --  -37.78 -37.00-120.00   32
  8  ω    -58.00 -19.00   1.00    1.00    --  -37.78 -37.00-120.00   39
  9  ω   -103.00 -12.00   1.00    1.00    --  -37.78 -77.00   0.00   91
 10  ω    -66.00 -40.00   1.00    1.00    --  -37.78 178.00  90.00   26
 11  ω     65.00  92.00   1.00    1.00    --   37.78-138.00-123.00   27
 12  ω    111.00 136.00   1.00    1.00    --  111.00 -77.00  60.00   25
 13  ω     44.00  87.00   1.00    1.00    --  111.00 -77.00  60.00   43
 14  ω     93.00 147.00   1.00    1.00    --  111.00 178.00 -30.00   54
 15  ω    112.00 137.00   1.00    1.00    --  111.00 -77.00  90.00   25
 16  ω    106.00 149.00   1.00    1.00    --  111.00  77.00-180.00   43
 17  ω     72.00  97.00   1.00    1.00    --  111.00 -94.00  60.00   25
 18  ω     69.00 112.00   1.00    1.00    --  111.00-111.00  30.00   43
 19  ω    100.00 126.00   1.00    1.00    --  111.00 178.00  60.00   26
 20  ω     58.00  84.00   1.00    1.00    --  111.00 -94.00 -90.00   26
 21  ω    112.00 172.00   1.00    1.00    --  111.00  45.00  60.00   60
 22  ω     57.00 107.00   1.00    1.00    --  111.00 -45.00 120.00   50
 23  ω     66.00 112.00   1.00    1.00    --  111.00-111.00 -90.00   46
 24  ω     58.00  90.00   1.00    1.00    --  111.00 178.00  60.00   32
 25  ω     64.00 116.00   1.00    1.00    --  111.00 -77.00-120.00   52
 26  ω    101.00 178.00   1.00    1.00    --  111.00  61.00  30.00   77
 27  ω     94.00 135.00   1.00    1.00    --  111.00 -15.00-120.00   41
 28  ω    133.00 178.00   1.00    1.00    --  111.00  30.00  90.00   45
 29  ω     43.00 127.00   1.00    1.00    --  111.00 -45.00 -90.00   84
 30  ω     42.00  68.00   1.00    1.00    --  111.00 -94.00  60.00   26
 31  ω    105.00 131.00   1.00    1.00    --  111.00  30.00  90.00   26
 32  ω     69.00 148.00   1.00    1.00    --  111.00 -15.00  60.00   79
 33  ω     50.00 107.00   1.00    1.00    --  111.00 -94.00 -60.00   57
 34  ω     59.00 100.00   1.00    1.00    --  111.00 -94.00 150.00   41
 35  ω     64.00 128.00   1.00    1.00    --  111.00 -45.00  30.00   64
 36  ω     49.00 101.00   1.00    1.00    --  111.00-111.00 150.00   52
 37  ω     56.00  81.00   1.00    1.00    --  111.00 -15.00-120.00   25
 38  ω    135.00 162.00   1.00    1.00    --  111.00  45.00 -30.00   27
 39  ω     74.00 100.00   1.00    1.00    --  111.00 -94.00  30.00   26
 40  ω     50.00  83.00   1.00    1.00    --  111.00 -25.00  43.75   33
 41  ω     42.00  67.00   1.00    1.00    --  111.00-111.00 120.00   25
 42  ω    114.00 143.00   1.00    1.00    --  111.00 111.00-180.00   29
 43  ω     78.00 103.00   1.00    1.00    --  111.00  15.00-180.00   25
 44  ω     44.00  90.00   1.00    1.00    --  111.00 -48.00-129.05   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0643856000
_diffrn_orient_matrix_UB_12      -0.1578280000
_diffrn_orient_matrix_UB_13      -0.0052934000
_diffrn_orient_matrix_UB_21      -0.0009068000
_diffrn_orient_matrix_UB_22      0.0356585000
_diffrn_orient_matrix_UB_23      -0.1436099000
_diffrn_orient_matrix_UB_31      0.1534914000
_diffrn_orient_matrix_UB_32      -0.0118906000
_diffrn_orient_matrix_UB_33      0.0035147000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3853
_reflns_number_total             4233
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    ?
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         4233
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.031
_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)+(0.0682P)²+0.2831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1145
_refine_ls_wR_factor_ref         0.1190
_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 C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.01 and sigma
for terminal atoms of 0.02
3. Same fragment restrains
{C1B, O2B, C3B, C4B, C5B, C1A, O2A, C3A, C4A, C5A, B6, N7, C8, C9, C10, O11,
O12, C13, C14, O15, O16} sigma for 1-2: 0.02, 1-3: 0.04
as
{C1A, O2A, C3A, C4A, C5A, C1B, O2B, C3B, C4B, C5B, B6, N7, C8, C9, C10, O11,
O12, C13, C14, O15, O16}
4. Others
 Sof(C1B)=Sof(O2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B1)=
 Sof(H5B2)=Sof(H5B3)=1-FVAR(1)
 Sof(C1A)=Sof(O2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A1)=
 Sof(H5A2)=Sof(H5A3)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C13(H13A,H13B), C29(H29A,H29B), C33(H33A,H33B)
5.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C3B(H3B), C4B(H4B), C23(H23), C24(H24)
5.c Idealised Me refined as rotating group:
 C5A(H5A1,H5A2,H5A3), C5B(H5B1,H5B2,H5B3), C8(H8A,H8B,H8C), C25(H25A,H25B,
 H25C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C1A C 0.8201(3) 0.7406(3) 0.8619(4) 0.0263(6) Uani 0.903(4) 1 d D U P A 1
O2A O 0.7057(2) 0.84448(18) 0.87423(17) 0.0304(4) Uani 0.903(4) 1 d D U P A 1
C3A C 0.9601(2) 0.7298(2) 0.89246(17) 0.0335(4) Uani 0.903(4) 1 d D U P A 1
H3A H 1.045065 0.657026 0.866518 0.040 Uiso 0.903(4) 1 calc R . P A 1
C4A C 0.97427(18) 0.81582(17) 0.95409(16) 0.0305(4) Uani 0.903(4) 1 d D U P A 1
H4A H 0.888217 0.890896 0.975631 0.037 Uiso 0.903(4) 1 calc R . P A 1
C5A C 1.1141(2) 0.8052(2) 0.9929(2) 0.0417(5) Uani 0.903(4) 1 d D U P A 1
H5A1 H 1.194139 0.723395 0.966413 0.063 Uiso 0.903(4) 1 calc GR . P A 1
H5A2 H 1.117252 0.794475 1.083843 0.063 Uiso 0.903(4) 1 calc GR . P A 1
H5A3 H 1.122738 0.890911 0.953845 0.063 Uiso 0.903(4) 1 calc GR . P A 1
C1B C 0.797(2) 0.756(2) 0.859(4) 0.016(5) Uiso 0.097(4) 1 d D U P A 2
O2B O 0.6673(17) 0.8534(19) 0.8649(19) 0.029(5) Uiso 0.097(4) 1 d D U P A 2
C3B C 0.9023(18) 0.797(2) 0.8991(17) 0.039(4) Uiso 0.097(4) 1 d D U P A 2
H3B H 0.865320 0.891836 0.909447 0.047 Uiso 0.097(4) 1 calc R . P A 2
C4B C 1.0392(17) 0.7192(19) 0.9217(17) 0.041(4) Uiso 0.097(4) 1 d D U P A 2
H4B H 1.074555 0.625952 0.906801 0.049 Uiso 0.097(4) 1 calc R . P A 2
C5B C 1.151(2) 0.751(3) 0.967(2) 0.047(5) Uiso 0.097(4) 1 d D U P A 2
H5B1 H 1.221590 0.748380 0.901248 0.070 Uiso 0.097(4) 1 calc GR . P A 2
H5B2 H 1.200329 0.681091 1.040967 0.070 Uiso 0.097(4) 1 calc GR . P A 2
H5B3 H 1.104553 0.845213 0.988718 0.070 Uiso 0.097(4) 1 calc GR . P A 2
B6 B 0.81083(17) 0.61389(16) 0.81173(13) 0.0242(3) Uani 1 1 d D U . . .
N7 N 0.75622(12) 0.65542(11) 0.66659(10) 0.0218(2) Uani 1 1 d D U . . .
C8 C 0.78087(17) 0.77308(15) 0.58962(13) 0.0293(3) Uani 1 1 d D U . . .
H8A H 0.752824 0.786007 0.502757 0.044 Uiso 1 1 calc GR . . . .
H8B H 0.883372 0.750535 0.593813 0.044 Uiso 1 1 calc GR . . . .
H8C H 0.722618 0.859993 0.621721 0.044 Uiso 1 1 calc GR . . . .
C9 C 0.60022(14) 0.68798(14) 0.67626(13) 0.0264(3) Uani 1 1 d D U . . .
H9A H 0.574354 0.645654 0.615745 0.032 Uiso 1 1 calc R . . . .
H9B H 0.538803 0.791060 0.659220 0.032 Uiso 1 1 calc R . . . .
C10 C 0.57984(15) 0.62514(15) 0.80844(14) 0.0280(3) Uani 1 1 d D U . . .
O11 O 0.47045(12) 0.62077(12) 0.84775(11) 0.0384(3) Uani 1 1 d D U . . .
O12 O 0.69962(11) 0.57817(11) 0.87697(9) 0.0290(2) Uani 1 1 d D U . . .
C13 C 0.84492(14) 0.52115(14) 0.61979(12) 0.0239(3) Uani 1 1 d D U . . .
H13A H 0.786973 0.469740 0.617522 0.029 Uiso 1 1 calc R . . . .
H13B H 0.879569 0.540901 0.534611 0.029 Uiso 1 1 calc R . . . .
C14 C 0.97053(15) 0.43562(14) 0.70944(13) 0.0262(3) Uani 1 1 d D U . . .
O15 O 1.07459(11) 0.33029(11) 0.69132(10) 0.0347(3) Uani 1 1 d D U . . .
O16 O 0.95023(11) 0.49000(10) 0.81191(9) 0.0288(2) Uani 1 1 d D U . . .
C21 C 0.64120(15) 0.27269(15) 0.64956(13) 0.0272(3) Uani 1 1 d . U . . .
O22 O 0.65252(12) 0.35812(12) 0.70272(11) 0.0364(3) Uani 1 1 d . U . . .
C23 C 0.75143(16) 0.21010(16) 0.55819(14) 0.0305(3) Uani 1 1 d . U . . .
H23 H 0.834341 0.226722 0.553490 0.037 Uiso 1 1 calc R . . . .
C24 C 0.74456(15) 0.13195(15) 0.48141(13) 0.0293(3) Uani 1 1 d . U . . .
H24 H 0.667301 0.106487 0.491474 0.035 Uiso 1 1 calc R . . . .
C25 C 0.85047(18) 0.08171(19) 0.38047(16) 0.0389(4) Uani 1 1 d . U . . .
H25A H 0.928062 0.108976 0.384419 0.058 Uiso 1 1 calc GR . . . .
H25B H 0.801270 0.124275 0.299071 0.058 Uiso 1 1 calc GR . . . .
H25C H 0.891520 -0.021061 0.391739 0.058 Uiso 1 1 calc GR . . . .
B26 B 0.49538(16) 0.25255(15) 0.67835(13) 0.0229(3) Uani 1 1 d . U . . .
N27 N 0.44334(11) 0.25479(11) 0.82349(10) 0.0205(2) Uani 1 1 d . U . . .
C28 C 0.56006(15) 0.19940(15) 0.92037(12) 0.0264(3) Uani 1 1 d . U . . .
H28A H 0.604192 0.263847 0.912481 0.040 Uiso 1 1 calc GR . . . .
H28B H 0.633823 0.106256 0.908505 0.040 Uiso 1 1 calc GR . . . .
H28C H 0.518609 0.191826 1.003564 0.040 Uiso 1 1 calc GR . . . .
C29 C 0.33915(14) 0.40549(13) 0.82247(12) 0.0237(3) Uani 1 1 d . U . . .
H29A H 0.387969 0.457161 0.847297 0.028 Uiso 1 1 calc R . . . .
H29B H 0.258555 0.412834 0.880131 0.028 Uiso 1 1 calc R . . . .
C30 C 0.28461(15) 0.46330(14) 0.68862(12) 0.0237(3) Uani 1 1 d . U . . .
O31 O 0.17932(11) 0.57144(10) 0.65330(9) 0.0310(2) Uani 1 1 d . U . . .
O32 O 0.37074(10) 0.37732(10) 0.61327(8) 0.0260(2) Uani 1 1 d . U . . .
C33 C 0.36839(14) 0.16221(13) 0.84002(12) 0.0228(3) Uani 1 1 d . U . . .
H33A H 0.262297 0.220025 0.834928 0.027 Uiso 1 1 calc R . . . .
H33B H 0.393683 0.098465 0.922300 0.027 Uiso 1 1 calc R . . . .
C34 C 0.41881(14) 0.07838(14) 0.73649(13) 0.0248(3) Uani 1 1 d . U . . .
O35 O 0.38830(11) -0.01393(11) 0.72697(11) 0.0339(3) Uani 1 1 d . U . . .
O36 O 0.49839(10) 0.12292(10) 0.65491(9) 0.0255(2) Uani 1 1 d . U . . .


_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
C1A O2A 1.234(3) . ?
C1A C3A 1.462(3) . ?
C1A B6 1.619(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.317(2) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.490(2) . ?
C5A H5A1 0.9800 . ?
C5A H5A2 0.9800 . ?
C5A H5A3 0.9800 . ?
C1B O2B 1.290(16) . ?
C1B C3B 1.470(15) . ?
C1B B6 1.662(13) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.296(16) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.494(17) . ?
C5B H5B1 0.9800 . ?
C5B H5B2 0.9800 . ?
C5B H5B3 0.9800 . ?
B6 N7 1.6337(17) . ?
B6 O12 1.4663(18) . ?
B6 O16 1.4630(18) . ?
N7 C8 1.4920(17) . ?
N7 C9 1.4919(16) . ?
N7 C13 1.4968(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.512(2) . ?
C10 O11 1.1989(18) . ?
C10 O12 1.3367(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5048(18) . ?
C14 O15 1.2050(18) . ?
C14 O16 1.3279(17) . ?
C21 O22 1.2372(17) . ?
C21 C23 1.470(2) . ?
C21 B26 1.621(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.332(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.495(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
B26 N27 1.6378(18) . ?
B26 O32 1.4788(17) . ?
B26 O36 1.4624(16) . ?
N27 C28 1.4965(16) . ?
N27 C29 1.4949(16) . ?
N27 C33 1.4991(16) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.5163(18) . ?
C30 O31 1.2019(17) . ?
C30 O32 1.3366(16) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.5070(18) . ?
C34 O35 1.2002(17) . ?
C34 O36 1.3343(17) . ?

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
O2A C1A C3A 121.93(19) . . ?
O2A C1A B6 117.7(2) . . ?
C3A C1A B6 120.39(19) . . ?
C1A C3A H3A 118.3 . . ?
C4A C3A C1A 123.31(18) . . ?
C4A C3A H3A 118.3 . . ?
C3A C4A H4A 117.3 . . ?
C3A C4A C5A 125.44(17) . . ?
C5A C4A H4A 117.3 . . ?
C4A C5A H5A1 109.5 . . ?
C4A C5A H5A2 109.5 . . ?
C4A C5A H5A3 109.5 . . ?
H5A1 C5A H5A2 109.5 . . ?
H5A1 C5A H5A3 109.5 . . ?
H5A2 C5A H5A3 109.5 . . ?
C3B C1B O2B 110.5(14) . . ?
C3B C1B B6 134.1(14) . . ?
B6 C1B O2B 115.4(14) . . ?
C1B C3B H3B 116.0 . . ?
C1B C3B C4B 127.9(18) . . ?
C4B C3B H3B 116.0 . . ?
C3B C4B H4B 114.5 . . ?
C5B C4B C3B 131.0(18) . . ?
C5B C4B H4B 114.5 . . ?
C4B C5B H5B1 109.5 . . ?
C4B C5B H5B2 109.5 . . ?
C4B C5B H5B3 109.5 . . ?
H5B1 C5B H5B2 109.5 . . ?
H5B1 C5B H5B3 109.5 . . ?
H5B2 C5B H5B3 109.5 . . ?
C1A B6 N7 113.71(19) . . ?
C1B B6 N7 109.9(14) . . ?
O12 B6 C1A 111.46(17) . . ?
O12 B6 C1B 106.8(12) . . ?
O12 B6 N7 101.81(10) . . ?
O16 B6 C1A 113.63(14) . . ?
O16 B6 C1B 121.1(6) . . ?
O16 B6 N7 103.12(10) . . ?
O16 B6 O12 112.28(12) . . ?
C8 N7 B6 114.64(10) . . ?
C8 N7 C13 110.46(10) . . ?
C9 N7 B6 103.82(10) . . ?
C9 N7 C8 112.85(11) . . ?
C9 N7 C13 112.20(10) . . ?
C13 N7 B6 102.29(9) . . ?
N7 C8 H8A 109.5 . . ?
N7 C8 H8B 109.5 . . ?
N7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N7 C9 H9A 110.5 . . ?
N7 C9 H9B 110.5 . . ?
N7 C9 C10 105.95(11) . . ?
H9A C9 H9B 108.7 . . ?
C10 C9 H9A 110.5 . . ?
C10 C9 H9B 110.5 . . ?
O11 C10 C9 124.93(14) . . ?
O11 C10 O12 124.35(14) . . ?
O12 C10 C9 110.69(11) . . ?
C10 O12 B6 113.49(11) . . ?
N7 C13 H13A 110.5 . . ?
N7 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 N7 106.32(10) . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
O15 C14 C13 124.33(12) . . ?
O15 C14 O16 124.56(13) . . ?
O16 C14 C13 111.10(11) . . ?
C14 O16 B6 112.87(10) . . ?
O22 C21 C23 118.05(13) . . ?
O22 C21 B26 115.71(12) . . ?
C23 C21 B26 125.95(12) . . ?
C21 C23 H23 117.3 . . ?
C24 C23 C21 125.31(14) . . ?
C24 C23 H23 117.3 . . ?
C23 C24 H24 117.9 . . ?
C23 C24 C25 124.27(14) . . ?
C25 C24 H24 117.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C21 B26 N27 113.96(11) . . ?
O32 B26 C21 109.77(11) . . ?
O32 B26 N27 100.64(10) . . ?
O36 B26 C21 117.21(11) . . ?
O36 B26 N27 103.27(10) . . ?
O36 B26 O32 110.63(11) . . ?
C28 N27 B26 116.52(10) . . ?
C28 N27 C29 112.58(10) . . ?
C28 N27 C33 109.97(10) . . ?
C29 N27 B26 103.74(9) . . ?
C29 N27 C33 111.83(10) . . ?
C33 N27 B26 101.63(9) . . ?
N27 C28 H28A 109.5 . . ?
N27 C28 H28B 109.5 . . ?
N27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N27 C29 H29A 110.8 . . ?
N27 C29 H29B 110.8 . . ?
N27 C29 C30 104.62(10) . . ?
H29A C29 H29B 108.9 . . ?
C30 C29 H29A 110.8 . . ?
C30 C29 H29B 110.8 . . ?
O31 C30 C29 125.56(12) . . ?
O31 C30 O32 123.86(12) . . ?
O32 C30 C29 110.58(11) . . ?
C30 O32 B26 113.74(10) . . ?
N27 C33 H33A 110.4 . . ?
N27 C33 H33B 110.4 . . ?
N27 C33 C34 106.74(10) . . ?
H33A C33 H33B 108.6 . . ?
C34 C33 H33A 110.4 . . ?
C34 C33 H33B 110.4 . . ?
O35 C34 C33 124.43(13) . . ?
O35 C34 O36 124.43(12) . . ?
O36 C34 C33 111.11(11) . . ?
C34 O36 B26 111.93(10) . . ?

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
C1A C3A C4A C5A 176.9(3) . . . . ?
C1A B6 N7 C8 23.74(19) . . . . ?
C1A B6 N7 C9 -99.82(17) . . . . ?
C1A B6 N7 C13 143.31(16) . . . . ?
C1A B6 O12 C10 104.82(18) . . . . ?
C1A B6 O16 C14 -137.4(2) . . . . ?
O2A C1A C3A C4A 11.9(6) . . . . ?
O2A C1A B6 N7 68.1(4) . . . . ?
O2A C1A B6 O12 -46.3(4) . . . . ?
O2A C1A B6 O16 -174.3(3) . . . . ?
C3A C1A B6 N7 -112.5(3) . . . . ?
C3A C1A B6 O12 133.1(3) . . . . ?
C3A C1A B6 O16 5.0(4) . . . . ?
C1B C3B C4B C5B -177(3) . . . . ?
C1B B6 N7 C8 30.7(9) . . . . ?
C1B B6 N7 C9 -92.8(9) . . . . ?
C1B B6 N7 C13 150.3(9) . . . . ?
C1B B6 O12 C10 98.5(12) . . . . ?
C1B B6 O16 C14 -137.2(18) . . . . ?
O2B C1B C3B C4B 170(2) . . . . ?
O2B C1B B6 N7 65(3) . . . . ?
O2B C1B B6 O12 -44(3) . . . . ?
O2B C1B B6 O16 -174(2) . . . . ?
C3B C1B B6 N7 -115(4) . . . . ?
C3B C1B B6 O12 135(4) . . . . ?
C3B C1B B6 O16 5(5) . . . . ?
B6 C1A C3A C4A -167.4(2) . . . . ?
B6 C1B C3B C4B -10(6) . . . . ?
B6 N7 C9 C10 -17.04(12) . . . . ?
B6 N7 C13 C14 -18.98(13) . . . . ?
N7 B6 O12 C10 -16.76(13) . . . . ?
N7 B6 O16 C14 -13.85(15) . . . . ?
N7 C9 C10 O11 -173.78(12) . . . . ?
N7 C9 C10 O12 7.88(14) . . . . ?
N7 C13 C14 O15 -169.06(13) . . . . ?
N7 C13 C14 O16 12.14(15) . . . . ?
C8 N7 C9 C10 -141.77(11) . . . . ?
C8 N7 C13 C14 103.48(12) . . . . ?
C9 N7 C13 C14 -129.65(11) . . . . ?
C9 C10 O12 B6 6.63(15) . . . . ?
O11 C10 O12 B6 -171.72(13) . . . . ?
O12 B6 N7 C8 143.74(11) . . . . ?
O12 B6 N7 C9 20.18(12) . . . . ?
O12 B6 N7 C13 -96.68(11) . . . . ?
O12 B6 O16 C14 94.97(13) . . . . ?
C13 N7 C9 C10 92.66(12) . . . . ?
C13 C14 O16 B6 1.97(16) . . . . ?
O15 C14 O16 B6 -176.84(13) . . . . ?
O16 B6 N7 C8 -99.75(13) . . . . ?
O16 B6 N7 C9 136.69(11) . . . . ?
O16 B6 N7 C13 19.83(13) . . . . ?
O16 B6 O12 C10 -126.40(12) . . . . ?
C21 C23 C24 C25 173.47(15) . . . . ?
C21 B26 N27 C28 -31.29(15) . . . . ?
C21 B26 N27 C29 93.04(12) . . . . ?
C21 B26 N27 C33 -150.78(11) . . . . ?
C21 B26 O32 C30 -104.55(12) . . . . ?
C21 B26 O36 C34 145.94(12) . . . . ?
O22 C21 C23 C24 -170.45(15) . . . . ?
O22 C21 B26 N27 -38.65(17) . . . . ?
O22 C21 B26 O32 73.34(15) . . . . ?
O22 C21 B26 O36 -159.38(12) . . . . ?
C23 C21 B26 N27 147.74(13) . . . . ?
C23 C21 B26 O32 -100.28(15) . . . . ?
C23 C21 B26 O36 27.0(2) . . . . ?
B26 C21 C23 C24 3.0(2) . . . . ?
B26 N27 C29 C30 24.23(12) . . . . ?
B26 N27 C33 C34 18.08(12) . . . . ?
N27 B26 O32 C30 15.88(14) . . . . ?
N27 B26 O36 C34 19.76(13) . . . . ?
N27 C29 C30 O31 164.38(13) . . . . ?
N27 C29 C30 O32 -15.96(14) . . . . ?
N27 C33 C34 O35 174.23(13) . . . . ?
N27 C33 C34 O36 -7.54(14) . . . . ?
C28 N27 C29 C30 151.07(11) . . . . ?
C28 N27 C33 C34 -105.96(11) . . . . ?
C29 N27 C33 C34 128.18(11) . . . . ?
C29 C30 O32 B26 -1.08(15) . . . . ?
O31 C30 O32 B26 178.58(13) . . . . ?
O32 B26 N27 C28 -148.68(10) . . . . ?
O32 B26 N27 C29 -24.36(12) . . . . ?
O32 B26 N27 C33 91.82(11) . . . . ?
O32 B26 O36 C34 -87.19(13) . . . . ?
C33 N27 C29 C30 -84.53(12) . . . . ?
C33 C34 O36 B26 -8.74(15) . . . . ?
O35 C34 O36 B26 169.49(13) . . . . ?
O36 B26 N27 C28 96.95(12) . . . . ?
O36 B26 N27 C29 -138.73(10) . . . . ?
O36 B26 N27 C33 -22.54(12) . . . . ?
O36 B26 O32 C30 124.57(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.811
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shengjia2
_database_code_depnum_ccdc_archive 'CCDC 1900591'
loop_
_audit_author_name
_audit_author_address
'Daniel Paley'
;Columbia University
United States of America
;
_audit_update_record             
;
2019-03-01 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;
_audit_creation_date             2019-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 B N O6'
_chemical_formula_sum            'C7 H10 B N O6'
_chemical_formula_weight         214.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C7 H10 B N O6'
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                   9.3307(3)
_cell_length_b                   21.4147(8)
_cell_length_c                   9.6557(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.438(4)
_cell_angle_gamma                90
_cell_volume                     1819.38(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4951
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6460
_cell_measurement_theta_min      4.1400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.176
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             896
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.0323
1 0 1 0.0321
0 1 0 0.0171
0 -1 0 0.0095
-1 0 0 0.0866
1 0 0 0.0859

_exptl_crystal_size_max          0.397
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9990 -0.0056 -1.0029 0.0403 -0.2776 -0.0233
0.9990 0.0056 1.0029 -0.0403 0.2776 0.0233
-0.0009 1.0000 -0.0005 -0.0712 -0.0103 -0.0018
0.0009 -1.0000 0.0005 0.0712 0.0103 0.0018
-0.9984 -0.0016 -0.0009 0.0192 -0.1505 0.0870
0.9984 0.0016 0.0009 -0.0192 0.1505 -0.0870

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.808
_diffrn_reflns_theta_min         4.129
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0549
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  -6.00   1.00    5.00    --  -64.00  57.00-120.00   65
  2  ω     61.00 125.00   1.00    1.00    --   67.35  57.00  60.00   64
  3  ω   -104.00 -58.00   1.00    1.00    --  -37.78 -57.00-120.00   46
  4  ω    -29.00  30.00   1.00    1.00    --  -37.78  57.00-150.00   59
  5  ω   -102.00 -74.00   1.00    1.00    --  -37.78-178.00-180.00   28
  6  ω    -68.00 -42.00   1.00    1.00    --  -37.78-178.00-180.00   26
  7  ω     29.00  75.00   1.00    1.00    --   37.78 -99.00-120.00   46
  8  ω     76.00 103.00   1.00    1.00    --   37.78  77.00 120.00   27
  9  ω     11.00  55.00   1.00    1.00    --   37.78  77.00 120.00   44
 10  ω     45.00  72.00   1.00    5.00    --  111.00-111.00  60.00   27
 11  ω    121.00 177.00   1.00    5.00    --  111.00  15.00-120.00   56
 12  ω     85.00 114.00   1.00    5.00    --  111.00  77.00-150.00   29
 13  ω    119.00 177.00   1.00    5.00    --  111.00  45.00  90.00   58
 14  ω     44.00  98.00   1.00    5.00    --  111.00 -94.00-180.00   54
 15  ω     41.00 113.00   1.00    5.00    --  111.00-111.00 150.00   72
 16  ω     89.00 115.00   1.00    5.00    --  111.00 -61.00 150.00   26
 17  ω     64.00  90.00   1.00    5.00    --  111.00-111.00 -90.00   26
 18  ω     71.00 109.00   1.00    5.00    --  111.00 -94.00-150.00   38
 19  ω     73.00 122.00   1.00    5.00    --  111.00-138.00 -22.00   49
 20  ω    139.00 177.00   1.00    5.00    --  111.00  77.00 -30.00   38
 21  ω     41.00  68.00   1.00    5.00    --  111.00-111.00  90.00   27
 22  ω     59.00  87.00   1.00    5.00    --  111.00 -61.00 150.00   28
 23  ω     97.00 122.00   1.00    5.00    --  111.00  77.00 -30.00   25
 24  ω     79.00 128.00   1.00    5.00    --  111.00 -30.00 150.00   49
 25  ω    132.00 174.00   1.00    5.00    --  111.00  77.00-150.00   42
 26  ω     53.00  94.00   1.00    5.00    --  111.00 -94.00 150.00   41
 27  ω     98.00 137.00   1.00    5.00    --  111.00 178.00   0.00   39
 28  ω     94.00 159.00   1.00    5.00    --  111.00  61.00 150.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0191355000
_diffrn_orient_matrix_UB_12      -0.0711935000
_diffrn_orient_matrix_UB_13      -0.0207230000
_diffrn_orient_matrix_UB_21      0.1506372000
_diffrn_orient_matrix_UB_22      -0.0100749000
_diffrn_orient_matrix_UB_23      0.1267822000
_diffrn_orient_matrix_UB_31      -0.0872708000
_diffrn_orient_matrix_UB_32      -0.0017819000
_diffrn_orient_matrix_UB_33      0.1101435000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3155
_reflns_number_total             3609
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3609
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.035
_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)+(0.0591P)²+0.5913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C25(H25A,H25B), C29(H29A,H29B)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C31(H31A,H31B,H31C), C35(H35A,H35B,
 H35C)
;
_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
B1 B 0.6422(2) 0.32968(9) 0.0842(2) 0.0144(4) Uani 1 1 d . . . . .
O2 O 0.70000(13) 0.29632(6) 0.22383(13) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.59899(19) 0.29057(8) 0.29318(19) 0.0162(3) Uani 1 1 d . . . . .
O4 O 0.61989(15) 0.26170(6) 0.40500(15) 0.0222(3) Uani 1 1 d . . . . .
C5 C 0.45183(18) 0.32401(8) 0.21014(19) 0.0161(3) Uani 1 1 d . . . . .
H5A H 0.369477 0.293543 0.165925 0.019 Uiso 1 1 calc R . . . .
H5B H 0.420376 0.351853 0.276694 0.019 Uiso 1 1 calc R . . . .
O6 O 0.73567(12) 0.38341(6) 0.07736(13) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.67930(17) 0.43709(8) 0.10490(17) 0.0138(3) Uani 1 1 d . . . . .
O8 O 0.73739(13) 0.48717(6) 0.10277(13) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.53411(17) 0.42675(7) 0.14044(18) 0.0133(3) Uani 1 1 d . . . . .
H9A H 0.553221 0.432066 0.246940 0.016 Uiso 1 1 calc R . . . .
H9B H 0.454645 0.456780 0.085998 0.016 Uiso 1 1 calc R . . . .
N10 N 0.48550(14) 0.36094(6) 0.09369(15) 0.0127(3) Uani 1 1 d . . . . .
C11 C 0.35445(17) 0.36164(8) -0.04670(18) 0.0157(3) Uani 1 1 d . . . . .
H11A H 0.267947 0.382845 -0.031215 0.024 Uiso 1 1 calc GR . . . .
H11B H 0.325888 0.318647 -0.078991 0.024 Uiso 1 1 calc GR . . . .
H11C H 0.383508 0.383869 -0.122017 0.024 Uiso 1 1 calc GR . . . .
O12 O 0.62581(13) 0.29263(5) -0.04469(14) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.55794(18) 0.23635(8) -0.06747(19) 0.0159(3) Uani 1 1 d . . . . .
O14 O 0.49987(14) 0.21381(6) 0.01575(14) 0.0186(3) Uani 1 1 d . . . . .
C15 C 0.56049(19) 0.20727(8) -0.20779(19) 0.0181(3) Uani 1 1 d . . . . .
H15A H 0.489414 0.229436 -0.291378 0.027 Uiso 1 1 calc GR . . . .
H15B H 0.530379 0.163319 -0.210575 0.027 Uiso 1 1 calc GR . . . .
H15C H 0.663344 0.210029 -0.213168 0.027 Uiso 1 1 calc GR . . . .
B21 B 0.73112(19) 0.44192(9) 0.5799(2) 0.0139(3) Uani 1 1 d . . . . .
O22 O 0.78493(13) 0.43883(6) 0.45441(13) 0.0170(3) Uani 1 1 d . . . . .
C23 C 0.93470(18) 0.43156(7) 0.49200(19) 0.0135(3) Uani 1 1 d . . . . .
O24 O 1.00368(13) 0.43505(5) 0.40737(14) 0.0170(3) Uani 1 1 d . . . . .
C25 C 1.00591(17) 0.42012(8) 0.65498(18) 0.0133(3) Uani 1 1 d . . . . .
H25A H 1.062931 0.380265 0.673038 0.016 Uiso 1 1 calc R . . . .
H25B H 1.076996 0.454340 0.701401 0.016 Uiso 1 1 calc R . . . .
O26 O 0.71143(12) 0.50552(5) 0.62227(13) 0.0157(3) Uani 1 1 d . . . . .
C27 C 0.79575(18) 0.51971(8) 0.75930(19) 0.0152(3) Uani 1 1 d . . . . .
O28 O 0.79134(15) 0.56923(6) 0.81662(16) 0.0235(3) Uani 1 1 d . . . . .
C29 C 0.89451(18) 0.46523(8) 0.83441(18) 0.0153(3) Uani 1 1 d . . . . .
H29A H 1.001889 0.478455 0.877797 0.018 Uiso 1 1 calc R . . . .
H29B H 0.860148 0.448199 0.913379 0.018 Uiso 1 1 calc R . . . .
N30 N 0.87795(14) 0.41744(6) 0.71743(15) 0.0115(3) Uani 1 1 d . . . . .
C31 C 0.86187(19) 0.35277(8) 0.76859(19) 0.0178(3) Uani 1 1 d . . . . .
H31A H 0.955853 0.340784 0.846350 0.027 Uiso 1 1 calc GR . . . .
H31B H 0.842283 0.323638 0.686081 0.027 Uiso 1 1 calc GR . . . .
H31C H 0.776945 0.351492 0.806874 0.027 Uiso 1 1 calc GR . . . .
O32 O 0.59710(13) 0.40352(6) 0.54513(13) 0.0162(3) Uani 1 1 d . . . . .
C33 C 0.51138(18) 0.40084(8) 0.63241(19) 0.0160(3) Uani 1 1 d . . . . .
O34 O 0.54485(13) 0.42698(6) 0.75017(14) 0.0195(3) Uani 1 1 d . . . . .
C35 C 0.37336(18) 0.36062(9) 0.56719(19) 0.0197(4) Uani 1 1 d . . . . .
H35A H 0.296932 0.383854 0.489745 0.030 Uiso 1 1 calc GR . . . .
H35B H 0.331200 0.348923 0.643918 0.030 Uiso 1 1 calc GR . . . .
H35C H 0.401925 0.322838 0.525350 0.030 Uiso 1 1 calc GR . . . .


_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
B1 O2 1.461(2) . ?
B1 O6 1.458(2) . ?
B1 N10 1.638(2) . ?
B1 O12 1.441(2) . ?
O2 C3 1.331(2) . ?
C3 O4 1.202(2) . ?
C3 C5 1.519(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N10 1.4911(19) . ?
O6 C7 1.327(2) . ?
C7 O8 1.205(2) . ?
C7 C9 1.520(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 N10 1.503(2) . ?
N10 C11 1.493(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
O12 C13 1.345(2) . ?
C13 O14 1.209(2) . ?
C13 C15 1.498(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
B21 O22 1.459(2) . ?
B21 O26 1.451(2) . ?
B21 N30 1.645(2) . ?
B21 O32 1.440(2) . ?
O22 C23 1.331(2) . ?
C23 O24 1.199(2) . ?
C23 C25 1.511(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 N30 1.5071(17) . ?
O26 C27 1.330(2) . ?
C27 O28 1.203(2) . ?
C27 C29 1.514(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 N30 1.494(2) . ?
N30 C31 1.495(2) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O32 C33 1.342(2) . ?
C33 O34 1.211(2) . ?
C33 C35 1.502(2) . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?

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
O2 B1 N10 102.15(12) . . ?
O6 B1 O2 112.66(14) . . ?
O6 B1 N10 103.80(13) . . ?
O12 B1 O2 115.36(14) . . ?
O12 B1 O6 106.77(13) . . ?
O12 B1 N10 115.65(13) . . ?
C3 O2 B1 113.82(13) . . ?
O2 C3 C5 110.96(14) . . ?
O4 C3 O2 124.67(16) . . ?
O4 C3 C5 124.35(15) . . ?
C3 C5 H5A 110.6 . . ?
C3 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
N10 C5 C3 105.53(12) . . ?
N10 C5 H5A 110.6 . . ?
N10 C5 H5B 110.6 . . ?
C7 O6 B1 113.05(12) . . ?
O6 C7 C9 111.18(13) . . ?
O8 C7 O6 123.85(14) . . ?
O8 C7 C9 124.97(15) . . ?
C7 C9 H9A 110.6 . . ?
C7 C9 H9B 110.6 . . ?
H9A C9 H9B 108.7 . . ?
N10 C9 C7 105.74(12) . . ?
N10 C9 H9A 110.6 . . ?
N10 C9 H9B 110.6 . . ?
C5 N10 B1 103.96(12) . . ?
C5 N10 C9 112.90(12) . . ?
C5 N10 C11 112.05(12) . . ?
C9 N10 B1 102.36(11) . . ?
C11 N10 B1 115.47(12) . . ?
C11 N10 C9 109.72(12) . . ?
N10 C11 H11A 109.5 . . ?
N10 C11 H11B 109.5 . . ?
N10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 O12 B1 122.94(13) . . ?
O12 C13 C15 111.84(14) . . ?
O14 C13 O12 122.66(16) . . ?
O14 C13 C15 125.48(16) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O22 B21 N30 103.40(12) . . ?
O26 B21 O22 112.80(14) . . ?
O26 B21 N30 102.76(13) . . ?
O32 B21 O22 107.03(14) . . ?
O32 B21 O26 114.83(13) . . ?
O32 B21 N30 115.57(13) . . ?
C23 O22 B21 113.52(13) . . ?
O22 C23 C25 111.16(13) . . ?
O24 C23 O22 124.05(16) . . ?
O24 C23 C25 124.77(15) . . ?
C23 C25 H25A 110.3 . . ?
C23 C25 H25B 110.3 . . ?
H25A C25 H25B 108.6 . . ?
N30 C25 C23 106.90(12) . . ?
N30 C25 H25A 110.3 . . ?
N30 C25 H25B 110.3 . . ?
C27 O26 B21 113.99(13) . . ?
O26 C27 C29 111.39(14) . . ?
O28 C27 O26 124.02(16) . . ?
O28 C27 C29 124.57(17) . . ?
C27 C29 H29A 110.6 . . ?
C27 C29 H29B 110.6 . . ?
H29A C29 H29B 108.7 . . ?
N30 C29 C27 105.82(13) . . ?
N30 C29 H29A 110.6 . . ?
N30 C29 H29B 110.6 . . ?
C25 N30 B21 102.87(12) . . ?
C29 N30 B21 103.95(12) . . ?
C29 N30 C25 112.34(12) . . ?
C29 N30 C31 112.43(13) . . ?
C31 N30 B21 114.46(12) . . ?
C31 N30 C25 110.33(12) . . ?
N30 C31 H31A 109.5 . . ?
N30 C31 H31B 109.5 . . ?
N30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C33 O32 B21 122.07(14) . . ?
O32 C33 C35 111.60(14) . . ?
O34 C33 O32 123.24(15) . . ?
O34 C33 C35 125.15(14) . . ?
C33 C35 H35A 109.5 . . ?
C33 C35 H35B 109.5 . . ?
C33 C35 H35C 109.5 . . ?
H35A C35 H35B 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?

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
B1 O2 C3 O4 175.42(17) . . . . ?
B1 O2 C3 C5 -3.1(2) . . . . ?
B1 O6 C7 O8 -178.88(16) . . . . ?
B1 O6 C7 C9 1.66(19) . . . . ?
B1 O12 C13 O14 3.2(3) . . . . ?
B1 O12 C13 C15 -178.30(14) . . . . ?
O2 B1 O6 C7 -99.28(16) . . . . ?
O2 B1 N10 C5 -18.39(16) . . . . ?
O2 B1 N10 C9 99.32(13) . . . . ?
O2 B1 N10 C11 -141.55(13) . . . . ?
O2 B1 O12 C13 47.6(2) . . . . ?
O2 C3 C5 N10 -9.91(18) . . . . ?
C3 C5 N10 B1 16.93(16) . . . . ?
C3 C5 N10 C9 -93.22(15) . . . . ?
C3 C5 N10 C11 142.29(14) . . . . ?
O4 C3 C5 N10 171.53(16) . . . . ?
O6 B1 O2 C3 124.19(14) . . . . ?
O6 B1 N10 C5 -135.69(13) . . . . ?
O6 B1 N10 C9 -17.98(16) . . . . ?
O6 B1 N10 C11 101.16(15) . . . . ?
O6 B1 O12 C13 173.65(14) . . . . ?
O6 C7 C9 N10 -14.20(17) . . . . ?
C7 C9 N10 B1 18.78(15) . . . . ?
C7 C9 N10 C5 129.92(13) . . . . ?
C7 C9 N10 C11 -104.32(14) . . . . ?
O8 C7 C9 N10 166.35(15) . . . . ?
N10 B1 O2 C3 13.45(17) . . . . ?
N10 B1 O6 C7 10.43(18) . . . . ?
N10 B1 O12 C13 -71.5(2) . . . . ?
O12 B1 O2 C3 -112.85(15) . . . . ?
O12 B1 O6 C7 133.08(14) . . . . ?
O12 B1 N10 C5 107.73(15) . . . . ?
O12 B1 N10 C9 -134.57(14) . . . . ?
O12 B1 N10 C11 -15.4(2) . . . . ?
B21 O22 C23 O24 -171.15(15) . . . . ?
B21 O22 C23 C25 7.36(18) . . . . ?
B21 O26 C27 O28 -177.13(14) . . . . ?
B21 O26 C27 C29 1.50(17) . . . . ?
B21 O32 C33 O34 -4.8(3) . . . . ?
B21 O32 C33 C35 176.52(14) . . . . ?
O22 B21 O26 C27 -120.36(14) . . . . ?
O22 B21 N30 C25 14.20(15) . . . . ?
O22 B21 N30 C29 131.49(13) . . . . ?
O22 B21 N30 C31 -105.50(14) . . . . ?
O22 B21 O32 C33 -173.73(14) . . . . ?
O22 C23 C25 N30 3.08(17) . . . . ?
C23 C25 N30 B21 -10.53(15) . . . . ?
C23 C25 N30 C29 -121.70(14) . . . . ?
C23 C25 N30 C31 111.99(14) . . . . ?
O24 C23 C25 N30 -178.41(15) . . . . ?
O26 B21 O22 C23 96.67(16) . . . . ?
O26 B21 N30 C25 -103.35(13) . . . . ?
O26 B21 N30 C29 13.94(14) . . . . ?
O26 B21 N30 C31 136.95(13) . . . . ?
O26 B21 O32 C33 -47.7(2) . . . . ?
O26 C27 C29 N30 8.38(16) . . . . ?
C27 C29 N30 B21 -13.23(15) . . . . ?
C27 C29 N30 C25 97.26(14) . . . . ?
C27 C29 N30 C31 -137.57(13) . . . . ?
O28 C27 C29 N30 -173.00(14) . . . . ?
N30 B21 O22 C23 -13.61(17) . . . . ?
N30 B21 O26 C27 -9.69(15) . . . . ?
N30 B21 O32 C33 71.74(19) . . . . ?
O32 B21 O22 C23 -136.09(13) . . . . ?
O32 B21 O26 C27 116.64(15) . . . . ?
O32 B21 N30 C25 130.80(14) . . . . ?
O32 B21 N30 C29 -111.91(15) . . . . ?
O32 B21 N30 C31 11.10(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.949
_oxdiff_exptl_absorpt_empirical_full_min 0.755
