# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_BG003_0m
_database_code_depnum_ccdc_archive 'CCDC 1482172'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C21 H39 B N2'
_chemical_formula_sum            'C21 H39 B N2'
_chemical_formula_weight         330.38
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   9.860(4)
_cell_length_b                   9.940(4)
_cell_length_c                   10.962(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.93(2)
_cell_angle_gamma                90
_cell_volume                     996.6(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    990
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.79
_cell_measurement_theta_min      2.87
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5586
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1067 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.7493.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1009
_exptl_crystal_description       plate
_exptl_crystal_F_000             368.1129
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0690
_diffrn_reflns_av_unetI/netI     0.1415
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6701
_diffrn_reflns_theta_full        27.9458
_diffrn_reflns_theta_max         27.95
_diffrn_reflns_theta_min         2.00
_diffrn_ambient_temperature      149.9
_diffrn_measured_fraction_theta_full 0.8266
_diffrn_measured_fraction_theta_max 0.8266
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.727
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2353
_reflns_number_total             3958
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_refine_diff_density_max         0.3832
_refine_diff_density_min         -0.3973
_refine_diff_density_rms         0.0957
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0(700)
_refine_ls_d_res_high            0.7583
_refine_ls_d_res_low             10.1689
_refine_ls_goodness_of_fit_ref   0.9969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3958
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1347
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      0.9969
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0684P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1688
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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:
 C6(H6), C10(H10), C14(H14), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b), C8(H8a,H8b), C11(H11a,H11b), C12(H12a,H12b), C13(H13a,H13b),
 C15(H15a,H15b), C16(H16a,H16b), C17(H17a,H17b), C19(H19a,H19b), C21(H21a,H21b)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C9(H9a,H9b,H9c), C20(H20a,H20b,H20c), C22(H22a,H22b,H22c),
 C0aa(H0aa,H0ab,H0ac)
;
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_refinement_flags_posn
N4 N -0.1515(3) -0.6950(3) -0.4136(3) 0.0226(8) Uani 1.000000 .
N18 N -0.3764(3) -0.7654(3) -0.4194(3) 0.0218(8) Uani 1.000000 .
C0aa C -0.0664(4) -0.4605(5) -0.4282(4) 0.0375(12) Uani 1.000000 .
H0aa H -0.013(2) -0.4070(6) -0.471(2) 0.0562(18) Uiso 1.000000 GR
H0ab H -0.1671(4) -0.4275(9) -0.456(2) 0.0562(18) Uiso 1.000000 GR
H0ac H -0.018(3) -0.4523(6) -0.3325(5) 0.0562(18) Uiso 1.000000 GR
C1 C -0.1607(4) -0.9817(4) -0.3452(4) 0.0304(10) Uani 1.000000 .
H1a H -0.223(2) -1.0540(11) -0.3345(18) 0.0456(15) Uiso 1.000000 GR
H1b H -0.200(2) -0.9499(7) -0.4364(4) 0.0456(15) Uiso 1.000000 GR
H1c H -0.0612(5) -1.0158(17) -0.3239(16) 0.0456(15) Uiso 1.000000 GR
C2 C -0.1577(4) -0.8654(4) -0.2530(3) 0.0255(10) Uani 1.000000 .
C3 C -0.0806(4) -0.7356(4) -0.2701(4) 0.0273(10) Uani 1.000000 .
C5 C -0.2972(4) -0.7144(4) -0.4860(3) 0.0206(9) Uani 1.000000 .
C6 C -0.3208(4) -0.6074(4) -0.7488(3) 0.0233(9) Uani 1.000000 .
H6 H -0.2654(4) -0.5258(4) -0.7036(3) 0.0280(11) Uiso 1.000000 R
C7 C -0.4567(4) -0.5602(5) -0.8688(4) 0.0332(11) Uani 1.000000 .
H7a H -0.5082(4) -0.4902(5) -0.8385(4) 0.0398(13) Uiso 1.000000 R
H7b H -0.4220(4) -0.5179(5) -0.9336(4) 0.0398(13) Uiso 1.000000 R
C8 C -0.5684(4) -0.6722(5) -0.9399(4) 0.0349(11) Uani 1.000000 .
H8a H -0.6627(4) -0.6289(5) -0.9923(4) 0.0419(14) Uiso 1.000000 R
H8b H -0.5331(4) -0.7190(5) -1.0021(4) 0.0419(14) Uiso 1.000000 R
C9 C -0.0943(4) -0.9200(5) -0.1114(4) 0.0360(12) Uani 1.000000 .
H9a H -0.089(3) -0.8471(8) -0.0495(4) 0.0540(18) Uiso 1.000000 GR
H9b H -0.1575(17) -0.992(2) -0.1013(8) 0.0540(18) Uiso 1.000000 GR
H9c H 0.0039(13) -0.956(3) -0.0930(10) 0.0540(18) Uiso 1.000000 GR
C10 C -0.3084(4) -0.8027(4) -0.2783(3) 0.0243(10) Uani 1.000000 .
H10 H -0.3721(4) -0.8666(4) -0.2535(3) 0.0291(12) Uiso 1.000000 R
C11 C -0.2757(4) -0.6769(5) -0.1912(4) 0.0338(11) Uani 1.000000 .
H11a H -0.3491(4) -0.6057(5) -0.2312(4) 0.0406(13) Uiso 1.000000 R
H11b H -0.2749(4) -0.6983(5) -0.1027(4) 0.0406(13) Uiso 1.000000 R
C12 C -0.1207(4) -0.6316(5) -0.1832(4) 0.0361(12) Uani 1.000000 .
H12a H -0.0493(4) -0.6345(5) -0.0913(4) 0.0434(14) Uiso 1.000000 R
H12b H -0.1236(4) -0.5393(5) -0.2179(4) 0.0434(14) Uiso 1.000000 R
C13 C -0.5963(4) -0.7778(4) -0.8497(4) 0.0294(10) Uani 1.000000 .
H13a H -0.6709(4) -0.7418(4) -0.8181(4) 0.0353(12) Uiso 1.000000 R
H13b H -0.6382(4) -0.8589(4) -0.9028(4) 0.0353(12) Uiso 1.000000 R
C14 C -0.4606(4) -0.8213(4) -0.7280(3) 0.0219(9) Uani 1.000000 .
H14 H -0.4955(4) -0.8771(4) -0.6696(3) 0.0263(11) Uiso 1.000000 R
C15 C -0.3502(4) -0.9059(4) -0.7650(4) 0.0262(10) Uani 1.000000 .
H15a H -0.2716(4) -0.9360(4) -0.6829(4) 0.0314(12) Uiso 1.000000 R
H15b H -0.4009(4) -0.9873(4) -0.8124(4) 0.0314(12) Uiso 1.000000 R
C16 C -0.2795(4) -0.8339(4) -0.8505(4) 0.0283(10) Uani 1.000000 .
H16a H -0.1989(4) -0.8901(4) -0.8556(4) 0.0340(12) Uiso 1.000000 R
H16b H -0.3531(4) -0.8236(4) -0.9408(4) 0.0340(12) Uiso 1.000000 R
C17 C -0.2188(4) -0.6939(4) -0.7962(4) 0.0267(9) Uani 1.000000 .
H17a H -0.1988(4) -0.6436(4) -0.8656(4) 0.0321(11) Uiso 1.000000 R
H17b H -0.1245(4) -0.7060(4) -0.7216(4) 0.0321(11) Uiso 1.000000 R
C19 C -0.5364(3) -0.7865(4) -0.4755(3) 0.0228(9) Uani 1.000000 .
H19a H -0.5751(3) -0.7569(4) -0.5685(3) 0.0274(11) Uiso 1.000000 R
H19b H -0.5573(3) -0.8837(4) -0.4738(3) 0.0274(11) Uiso 1.000000 R
C20 C -0.6153(4) -0.7093(5) -0.4004(4) 0.0311(11) Uani 1.000000 .
H20a H -0.587(2) -0.6143(7) -0.394(2) 0.0466(16) Uiso 1.000000 GR
H20b H -0.7212(4) -0.717(2) -0.4473(15) 0.0466(16) Uiso 1.000000 GR
H20c H -0.588(2) -0.7472(18) -0.3119(10) 0.0466(16) Uiso 1.000000 GR
C21 C -0.0675(4) -0.6055(4) -0.4672(4) 0.0263(10) Uani 1.000000 .
H21a H 0.0346(4) -0.6382(4) -0.4370(4) 0.0315(12) Uiso 1.000000 R
H21b H -0.1094(4) -0.6117(4) -0.5644(4) 0.0315(12) Uiso 1.000000 R
C22 C 0.0860(4) -0.7517(5) -0.2307(4) 0.0386(12) Uani 1.000000 .
H22a H 0.1293(6) -0.6643(7) -0.236(3) 0.0579(18) Uiso 1.000000 GR
H22b H 0.1291(6) -0.786(3) -0.1404(11) 0.0579(18) Uiso 1.000000 GR
H22c H 0.1054(4) -0.815(2) -0.2905(18) 0.0579(18) Uiso 1.000000 GR
B1 B -0.3873(4) -0.6821(5) -0.6480(4) 0.0234(10) Uani 1.000000 .
H1 H -0.4726(4) -0.6254(5) -0.6519(4) 0.0281(12) Uiso 1.000000 R


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
N4 C3 1.518(5) . ?
N4 C5 1.371(4) . ?
N4 C21 1.478(5) . ?
N18 C5 1.351(4) . ?
N18 C10 1.485(4) . ?
N18 C19 1.478(4) . ?
C0aa H0aa 0.9800 . ?
C0aa H0ab 0.9800 . ?
C0aa H0ac 0.9800 . ?
C0aa C21 1.503(6) . ?
C1 H1a 0.9800 . ?
C1 H1b 0.9800 . ?
C1 H1c 0.9800 . ?
C1 C2 1.529(6) . ?
C2 C3 1.545(6) . ?
C2 C9 1.540(5) . ?
C2 C10 1.538(5) . ?
C3 C12 1.553(6) . ?
C3 C22 1.543(5) . ?
C5 B1 1.693(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.558(5) . ?
C6 C17 1.552(5) . ?
C6 B1 1.656(6) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 C8 1.555(6) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C13 1.535(6) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C10 H10 1.0000 . ?
C10 C11 1.533(6) . ?
C11 H11a 0.9900 . ?
C11 H11b 0.9900 . ?
C11 C12 1.563(6) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C13 H13a 0.9900 . ?
C13 H13b 0.9900 . ?
C13 C14 1.557(5) . ?
C14 H14 1.0000 . ?
C14 C15 1.544(5) . ?
C14 B1 1.653(6) . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.538(5) . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C16 C17 1.544(6) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.532(5) . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C21 H21a 0.9900 . ?
C21 H21b 0.9900 . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?
B1 H1 1.0000 . ?

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
C5 N4 C3 122.7(3) . . ?
C21 N4 C3 117.6(3) . . ?
C21 N4 C5 118.4(3) . . ?
C10 N18 C5 121.9(3) . . ?
C19 N18 C5 124.8(3) . . ?
C19 N18 C10 113.3(3) . . ?
H0ab C0aa H0aa 109.5 . . ?
H0ac C0aa H0aa 109.5 . . ?
H0ac C0aa H0ab 109.5 . . ?
C21 C0aa H0aa 109.5 . . ?
C21 C0aa H0ab 109.5 . . ?
C21 C0aa H0ac 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C2 C1 H1a 109.5 . . ?
C2 C1 H1b 109.5 . . ?
C2 C1 H1c 109.5 . . ?
C3 C2 C1 116.1(3) . . ?
C9 C2 C1 107.5(3) . . ?
C9 C2 C3 112.5(3) . . ?
C10 C2 C1 114.1(3) . . ?
C10 C2 C3 97.2(3) . . ?
C10 C2 C9 109.0(3) . . ?
C2 C3 N4 106.9(3) . . ?
C12 C3 N4 109.6(3) . . ?
C12 C3 C2 103.4(3) . . ?
C22 C3 N4 110.3(3) . . ?
C22 C3 C2 113.6(3) . . ?
C22 C3 C12 112.7(3) . . ?
N18 C5 N4 115.6(3) . . ?
B1 C5 N4 127.3(3) . . ?
B1 C5 N18 117.1(3) . . ?
C7 C6 H6 108.2(2) . . ?
C17 C6 H6 108.2(2) . . ?
C17 C6 C7 110.1(3) . . ?
B1 C6 H6 108.2(2) . . ?
B1 C6 C7 105.6(3) . . ?
B1 C6 C17 116.3(3) . . ?
H7a C7 C6 108.4(2) . . ?
H7b C7 C6 108.4(2) . . ?
H7b C7 H7a 107.4 . . ?
C8 C7 C6 115.6(4) . . ?
C8 C7 H7a 108.4(2) . . ?
C8 C7 H7b 108.4(2) . . ?
H8a C8 C7 108.4(2) . . ?
H8b C8 C7 108.4(2) . . ?
H8b C8 H8a 107.5 . . ?
C13 C8 C7 115.5(3) . . ?
C13 C8 H8a 108.4(2) . . ?
C13 C8 H8b 108.4(2) . . ?
H9a C9 C2 109.5 . . ?
H9b C9 C2 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C2 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
C2 C10 N18 108.6(3) . . ?
H10 C10 N18 110.85(19) . . ?
H10 C10 C2 110.8(2) . . ?
C11 C10 N18 110.7(3) . . ?
C11 C10 C2 104.7(3) . . ?
C11 C10 H10 110.8(2) . . ?
H11a C11 C10 110.9(2) . . ?
H11b C11 C10 110.9(2) . . ?
H11b C11 H11a 109.0 . . ?
C12 C11 C10 104.1(3) . . ?
C12 C11 H11a 110.9(2) . . ?
C12 C11 H11b 110.9(2) . . ?
C11 C12 C3 104.0(3) . . ?
H12a C12 C3 111.0(2) . . ?
H12a C12 C11 111.0(2) . . ?
H12b C12 C3 111.0(2) . . ?
H12b C12 C11 111.0(2) . . ?
H12b C12 H12a 109.0 . . ?
H13a C13 C8 108.3(2) . . ?
H13b C13 C8 108.3(2) . . ?
H13b C13 H13a 107.4 . . ?
C14 C13 C8 116.0(3) . . ?
C14 C13 H13a 108.27(19) . . ?
C14 C13 H13b 108.3(2) . . ?
H14 C14 C13 108.2(2) . . ?
C15 C14 C13 112.9(3) . . ?
C15 C14 H14 108.2(2) . . ?
B1 C14 C13 106.7(3) . . ?
B1 C14 H14 108.2(2) . . ?
B1 C14 C15 112.6(3) . . ?
H15a C15 C14 108.38(18) . . ?
H15b C15 C14 108.4(2) . . ?
H15b C15 H15a 107.4 . . ?
C16 C15 C14 115.6(3) . . ?
C16 C15 H15a 108.38(19) . . ?
C16 C15 H15b 108.4(2) . . ?
H16a C16 C15 109.1(2) . . ?
H16b C16 C15 109.10(19) . . ?
H16b C16 H16a 107.8 . . ?
C17 C16 C15 112.5(3) . . ?
C17 C16 H16a 109.10(19) . . ?
C17 C16 H16b 109.1(2) . . ?
C16 C17 C6 115.0(3) . . ?
H17a C17 C6 108.5(2) . . ?
H17a C17 C16 108.5(2) . . ?
H17b C17 C6 108.53(18) . . ?
H17b C17 C16 108.5(2) . . ?
H17b C17 H17a 107.5 . . ?
H19a C19 N18 109.10(18) . . ?
H19b C19 N18 109.1(2) . . ?
H19b C19 H19a 107.8 . . ?
C20 C19 N18 112.5(3) . . ?
C20 C19 H19a 109.1(2) . . ?
C20 C19 H19b 109.1(2) . . ?
H20a C20 C19 109.5 . . ?
H20b C20 C19 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C19 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
C0aa C21 N4 114.2(3) . . ?
H21a C21 N4 108.7(2) . . ?
H21a C21 C0aa 108.7(2) . . ?
H21b C21 N4 108.71(18) . . ?
H21b C21 C0aa 108.7(2) . . ?
H21b C21 H21a 107.6 . . ?
H22a C22 C3 109.5 . . ?
H22b C22 C3 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C3 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
C6 B1 C5 127.0(3) . . ?
C14 B1 C5 110.6(3) . . ?
C14 B1 C6 103.0(3) . . ?
H1 B1 C5 104.79(19) . . ?
H1 B1 C6 104.8(2) . . ?
H1 B1 C14 104.79(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AJ002_0m
_database_code_depnum_ccdc_archive 'CCDC 1482173'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H35 B N2 O2'
_chemical_formula_sum            'C21 H35 B N2 O2'
_chemical_formula_weight         358.35
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.692(2)
_cell_length_b                   16.559(6)
_cell_length_c                   17.724(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1964.1(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1348
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.20
_cell_measurement_temperature    150(2)
_exptl_crystal_description       prism
_exptl_absorpt_coefficient_mu    0.076

_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0593 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.9244.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.2117
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784.3144
_exptl_absorpt_correction_T_max  0.7456
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8687
_diffrn_reflns_theta_full        27.6962
_diffrn_reflns_theta_max         27.70
_diffrn_reflns_theta_min         2.30
_diffrn_ambient_temperature      149.95
_diffrn_measured_fraction_theta_full 0.9355
_diffrn_measured_fraction_theta_max 0.9355
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.865
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              22
_reflns_limit_l_min              -22
_reflns_number_gt                2936
_reflns_number_total             4295
_reflns_threshold_expression     I>=2u(I)
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.3346
_refine_diff_density_min         -0.3299
_refine_diff_density_rms         0.0855
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -2.0(6)
_refine_ls_d_res_high            0.7646
_refine_ls_d_res_low             8.8619
_refine_ls_goodness_of_fit_ref   0.9964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    54
_refine_ls_number_parameters     238
_refine_ls_number_reflns         4295
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      0.9964
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1140
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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:
 C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C16(H16), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C12(H12a,H12b), C14(H14a,H14b), C15(H15a,H15b),
 C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b)
2.c Idealised Me refined as rotating group:
 C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C20(H20a,H20b,H20c), C21(H21a,H21b,H21c)
;
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_refinement_flags_posn
O1 O -0.1676(3) 0.23040(10) -0.53977(9) 0.0268(4) Uani 1.000000 .
O2 O -0.0095(3) 0.12347(9) -0.38413(9) 0.0244(4) Uani 1.000000 .
N1 N -0.0234(3) 0.03539(11) -0.48357(11) 0.0173(4) Uani 1.000000 .
N2 N -0.1220(3) 0.10121(11) -0.57882(12) 0.0190(4) Uani 1.000000 .
C1 C -0.3796(4) -0.15628(16) -0.58397(16) 0.0287(6) Uani 1.000000 .
H1a H -0.5034(4) -0.15352(16) -0.55352(16) 0.0344(8) Uiso 1.000000 R
H1b H -0.3812(4) -0.20819(16) -0.61167(16) 0.0344(8) Uiso 1.000000 R
C2 C -0.3825(4) -0.08727(15) -0.64149(15) 0.0256(6) Uani 1.000000 .
H2a H -0.4773(4) -0.10172(15) -0.68221(15) 0.0307(8) Uiso 1.000000 R
H2b H -0.4354(4) -0.03842(15) -0.61622(15) 0.0307(8) Uiso 1.000000 R
C3 C -0.1814(4) -0.06578(14) -0.67770(14) 0.0191(6) Uani 1.000000 .
H3 H -0.1987(4) -0.01446(14) -0.70672(14) 0.0229(7) Uiso 1.000000 R
C4 C -0.0599(3) 0.02620(13) -0.55921(14) 0.0188(5) Uani 1.000000 .
C5 C 0.0739(4) -0.01067(13) -0.42266(13) 0.0179(5) Uani 1.000000 .
H5 H 0.0110(4) -0.06522(13) -0.41810(13) 0.0215(6) Uiso 1.000000 R
C6 C 0.2994(4) -0.01950(14) -0.43590(14) 0.0204(6) Uani 1.000000 .
H6 H 0.3183(4) -0.04326(14) -0.48727(14) 0.0245(7) Uiso 1.000000 R
C7 C 0.4111(4) 0.05927(15) -0.43371(15) 0.0300(7) Uani 1.000000 .
H7a H 0.5490(8) 0.0506(2) -0.4505(9) 0.0450(10) Uiso 1.000000 GR
H7b H 0.3456(15) 0.0983(3) -0.4671(7) 0.0450(10) Uiso 1.000000 GR
H7c H 0.412(2) 0.0803(5) -0.3820(2) 0.0450(10) Uiso 1.000000 GR
C8 C -0.4132(4) 0.16547(18) -0.75631(16) 0.0351(7) Uani 1.000000 .
H8a H -0.393(3) 0.2241(2) -0.7543(2) 0.0527(11) Uiso 1.000000 GR
H8b H -0.3144(18) 0.1414(8) -0.7903(3) 0.0527(11) Uiso 1.000000 GR
H8c H -0.5480(10) 0.1538(9) -0.7749(4) 0.0527(11) Uiso 1.000000 GR
C9 C -0.3883(4) 0.13003(15) -0.67758(14) 0.0224(6) Uani 1.000000 .
H9 H -0.4074(4) 0.07031(15) -0.68191(14) 0.0269(7) Uiso 1.000000 R
C10 C -0.1754(4) 0.14426(14) -0.64933(14) 0.0191(6) Uani 1.000000 .
H10 H -0.0780(4) 0.12988(14) -0.68995(14) 0.0230(7) Uiso 1.000000 R
C11 C -0.1170(4) 0.15472(15) -0.51892(15) 0.0215(6) Uani 1.000000 .
C12 C -0.1345(4) 0.23101(15) -0.62165(14) 0.0244(6) Uani 1.000000 .
H12a H -0.2265(4) 0.26960(15) -0.64644(14) 0.0293(7) Uiso 1.000000 R
H12b H 0.0047(4) 0.24699(15) -0.63329(14) 0.0293(7) Uiso 1.000000 R
C13 C -0.0541(4) 0.11345(14) -0.45885(14) 0.0203(6) Uani 1.000000 .
C14 C 0.0151(4) 0.04190(14) -0.35485(13) 0.0240(6) Uani 1.000000 .
H14a H 0.1208(4) 0.04055(14) -0.31582(13) 0.0288(7) Uiso 1.000000 R
H14b H -0.1113(4) 0.02237(14) -0.33225(13) 0.0288(7) Uiso 1.000000 R
C15 C -0.2005(4) -0.15618(16) -0.53041(15) 0.0245(6) Uani 1.000000 .
H15a H -0.2268(4) -0.11697(16) -0.48943(15) 0.0294(7) Uiso 1.000000 R
H15b H -0.1895(4) -0.21031(16) -0.50707(15) 0.0294(7) Uiso 1.000000 R
C16 C -0.0002(4) -0.13525(12) -0.56670(13) 0.0171(5) Uani 1.000000 .
H16 H 0.1013(4) -0.12922(12) -0.52568(13) 0.0206(6) Uiso 1.000000 R
C17 C 0.0743(4) -0.20036(14) -0.62206(14) 0.0229(6) Uani 1.000000 .
H17a H 0.2132(4) -0.18710(14) -0.63671(14) 0.0275(7) Uiso 1.000000 R
H17b H 0.0775(4) -0.25282(14) -0.59529(14) 0.0275(7) Uiso 1.000000 R
C18 C -0.0503(4) -0.21036(14) -0.69414(14) 0.0234(6) Uani 1.000000 .
H18a H 0.0246(4) -0.24453(14) -0.73019(14) 0.0281(7) Uiso 1.000000 R
H18b H -0.1759(4) -0.23887(14) -0.68145(14) 0.0281(7) Uiso 1.000000 R
C19 C -0.1013(4) -0.13070(14) -0.73214(14) 0.0260(6) Uani 1.000000 .
H19a H -0.2029(4) -0.14076(14) -0.77164(14) 0.0312(8) Uiso 1.000000 R
H19b H 0.0200(4) -0.10963(14) -0.75733(14) 0.0312(8) Uiso 1.000000 R
C20 C 0.3848(4) -0.07872(16) -0.37916(16) 0.0337(7) Uani 1.000000 .
H20a H 0.364(2) -0.0579(5) -0.32798(16) 0.0505(11) Uiso 1.000000 GR
H20b H 0.3171(17) -0.1309(3) -0.3844(6) 0.0505(11) Uiso 1.000000 GR
H20c H 0.5281(6) -0.0856(8) -0.3884(6) 0.0505(11) Uiso 1.000000 GR
C21 C -0.5488(4) 0.16153(18) -0.62476(16) 0.0374(7) Uani 1.000000 .
H21a H -0.6785(6) 0.1389(8) -0.6393(6) 0.0561(11) Uiso 1.000000 GR
H21b H -0.5174(14) 0.1454(9) -0.5729(2) 0.0561(11) Uiso 1.000000 GR
H21c H -0.5541(18) 0.22057(19) -0.6279(7) 0.0561(11) Uiso 1.000000 GR
B1 B -0.0135(4) -0.05034(15) -0.61237(16) 0.0191(6) Uani 1.000000 .
H1 H 0.1180(4) -0.04095(15) -0.63775(16) 0.0230(7) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.350(3) . ?
O1 C12 1.468(3) . ?
O2 C13 1.368(3) . ?
O2 C14 1.456(3) . ?
N1 C4 1.371(3) . ?
N1 C5 1.473(3) . ?
N1 C13 1.380(3) . ?
N2 C4 1.355(3) . ?
N2 C10 1.482(3) . ?
N2 C11 1.383(3) . ?
C1 H1a 0.9900 . ?
C1 H1b 0.9900 . ?
C1 C2 1.532(3) . ?
C1 C15 1.529(4) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.533(4) . ?
C3 H3 1.0000 . ?
C3 C19 1.541(3) . ?
C3 B1 1.634(4) . ?
C4 B1 1.610(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.534(3) . ?
C5 C14 1.535(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.504(3) . ?
C6 C20 1.516(3) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
C8 C9 1.523(4) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(4) . ?
C9 C21 1.517(4) . ?
C10 H10 1.0000 . ?
C10 C12 1.542(3) . ?
C11 C13 1.333(3) . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.526(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.541(3) . ?
C16 B1 1.625(3) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C17 C18 1.535(3) . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C18 C19 1.520(3) . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
B1 H1 1.0000 . ?

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
C12 O1 C11 103.85(19) . . ?
C14 O2 C13 104.91(17) . . ?
C5 N1 C4 137.5(2) . . ?
C13 N1 C4 112.81(19) . . ?
C13 N1 C5 108.54(19) . . ?
C10 N2 C4 137.0(2) . . ?
C11 N2 C4 112.5(2) . . ?
C11 N2 C10 110.17(18) . . ?
H1b C1 H1a 107.5 . . ?
C2 C1 H1a 108.52(14) . . ?
C2 C1 H1b 108.52(14) . . ?
C15 C1 H1a 108.52(15) . . ?
C15 C1 H1b 108.52(14) . . ?
C15 C1 C2 115.0(2) . . ?
H2a C2 C1 108.25(14) . . ?
H2b C2 C1 108.25(14) . . ?
H2b C2 H2a 107.4 . . ?
C3 C2 C1 116.1(2) . . ?
C3 C2 H2a 108.25(14) . . ?
C3 C2 H2b 108.25(13) . . ?
H3 C3 C2 108.12(13) . . ?
C19 C3 C2 113.9(2) . . ?
C19 C3 H3 108.12(13) . . ?
B1 C3 C2 110.1(2) . . ?
B1 C3 H3 108.12(12) . . ?
B1 C3 C19 108.3(2) . . ?
N2 C4 N1 101.75(19) . . ?
B1 C4 N1 128.7(2) . . ?
B1 C4 N2 129.1(2) . . ?
H5 C5 N1 109.92(12) . . ?
C6 C5 N1 111.83(19) . . ?
C6 C5 H5 109.92(12) . . ?
C14 C5 N1 99.59(17) . . ?
C14 C5 H5 109.92(13) . . ?
C14 C5 C6 115.2(2) . . ?
H6 C6 C5 107.55(13) . . ?
C7 C6 C5 113.7(2) . . ?
C7 C6 H6 107.55(14) . . ?
C20 C6 C5 109.3(2) . . ?
C20 C6 H6 107.55(14) . . ?
C20 C6 C7 110.9(2) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
C9 C8 H8a 109.5 . . ?
C9 C8 H8b 109.5 . . ?
C9 C8 H8c 109.5 . . ?
H9 C9 C8 107.27(15) . . ?
C10 C9 C8 110.0(2) . . ?
C10 C9 H9 107.27(13) . . ?
C21 C9 C8 110.8(2) . . ?
C21 C9 H9 107.27(15) . . ?
C21 C9 C10 113.9(2) . . ?
C9 C10 N2 115.3(2) . . ?
H10 C10 N2 109.58(12) . . ?
H10 C10 C9 109.58(13) . . ?
C12 C10 N2 97.87(19) . . ?
C12 C10 C9 114.4(2) . . ?
C12 C10 H10 109.58(14) . . ?
N2 C11 O1 112.2(2) . . ?
C13 C11 O1 140.7(2) . . ?
C13 C11 N2 107.0(2) . . ?
C10 C12 O1 106.3(2) . . ?
H12a C12 O1 110.46(13) . . ?
H12a C12 C10 110.46(13) . . ?
H12b C12 O1 110.46(13) . . ?
H12b C12 C10 110.46(15) . . ?
H12b C12 H12a 108.7 . . ?
N1 C13 O2 112.9(2) . . ?
C11 C13 O2 141.3(2) . . ?
C11 C13 N1 105.9(2) . . ?
C5 C14 O2 106.02(18) . . ?
H14a C14 O2 110.53(12) . . ?
H14a C14 C5 110.53(13) . . ?
H14b C14 O2 110.53(13) . . ?
H14b C14 C5 110.53(13) . . ?
H14b C14 H14a 108.7 . . ?
H15a C15 C1 108.46(15) . . ?
H15b C15 C1 108.46(14) . . ?
H15b C15 H15a 107.5 . . ?
C16 C15 C1 115.3(2) . . ?
C16 C15 H15a 108.46(13) . . ?
C16 C15 H15b 108.46(13) . . ?
H16 C16 C15 108.23(13) . . ?
C17 C16 C15 113.2(2) . . ?
C17 C16 H16 108.23(12) . . ?
B1 C16 C15 111.0(2) . . ?
B1 C16 H16 108.23(13) . . ?
B1 C16 C17 107.81(19) . . ?
H17a C17 C16 108.41(13) . . ?
H17b C17 C16 108.41(12) . . ?
H17b C17 H17a 107.5 . . ?
C18 C17 C16 115.46(19) . . ?
C18 C17 H17a 108.41(14) . . ?
C18 C17 H17b 108.41(13) . . ?
H18a C18 C17 108.89(13) . . ?
H18b C18 C17 108.89(14) . . ?
H18b C18 H18a 107.7 . . ?
C19 C18 C17 113.4(2) . . ?
C19 C18 H18a 108.89(14) . . ?
C19 C18 H18b 108.89(15) . . ?
C18 C19 C3 114.0(2) . . ?
H19a C19 C3 108.76(14) . . ?
H19a C19 C18 108.76(14) . . ?
H19b C19 C3 108.76(14) . . ?
H19b C19 C18 108.76(15) . . ?
H19b C19 H19a 107.7 . . ?
H20a C20 C6 109.5 . . ?
H20b C20 C6 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C6 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H21a C21 C9 109.5 . . ?
H21b C21 C9 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C9 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C4 B1 C3 113.9(2) . . ?
C16 B1 C3 104.79(19) . . ?
C16 B1 C4 113.6(2) . . ?
H1 B1 C3 108.10(13) . . ?
H1 B1 C4 108.10(13) . . ?
H1 B1 C16 108.10(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_AJ003_0m
_database_code_depnum_ccdc_archive 'CCDC 1482174'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H23 B N2 O2'
_chemical_formula_sum            'C13 H23 B N2 O2'
_chemical_formula_weight         250.16
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   8.0304(5)
_cell_length_b                   9.0974(5)
_cell_length_c                   19.4205(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1418.78(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4597
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.45
_cell_measurement_theta_min      2.47
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7056
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0764 before and 0.0332 after correction.
The Ratio of minimum to maximum transmission is 0.9464.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1710
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             544.2313
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10303
_diffrn_reflns_theta_full        27.5038
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_ambient_temperature      149.76
_diffrn_measured_fraction_theta_full 0.9942
_diffrn_measured_fraction_theta_max 0.9942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.989
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              25
_reflns_limit_l_min              -24
_reflns_number_gt                2744
_reflns_number_total             3244
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.2093
_refine_diff_density_min         -0.2202
_refine_diff_density_rms         0.0460
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(13)
_refine_ls_d_res_high            0.7695
_refine_ls_d_res_low             9.7103
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     178
_refine_ls_number_reflns         3244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.0359
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0469P)²+0.0409P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0875
_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:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C13(H13a,H13b,H13c)
;
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_refinement_flags_posn
O1 O -0.66119(13) 0.04040(12) -0.88119(5) 0.0257(3) Uani 1.000000 .
O2 O -0.89027(13) -0.03290(12) -1.02634(5) 0.0253(3) Uani 1.000000 .
N1 N -1.05522(14) -0.08580(13) -0.93408(6) 0.0187(3) Uani 1.000000 .
N2 N -0.91839(14) -0.03271(12) -0.84515(6) 0.0190(3) Uani 1.000000 .
C1 C -1.2265(2) 0.16772(16) -0.99858(10) 0.0342(4) Uani 1.000000 .
H1a H -1.3157(2) 0.24121(17) -0.9985(7) 0.0513(6) Uiso 1.000000 GR
H1b H -1.1539(13) 0.1835(6) -0.9587(4) 0.0513(6) Uiso 1.000000 GR
H1c H -1.1613(14) 0.1771(5) -1.0410(4) 0.0513(6) Uiso 1.000000 GR
C2 C -1.30224(18) 0.01407(15) -0.99480(8) 0.0240(3) Uani 1.000000 .
H2 H -1.36720(18) 0.00805(15) -0.95096(8) 0.0289(4) Uiso 1.000000 R
C3 C -1.16913(18) -0.10665(15) -0.99244(7) 0.0207(3) Uani 1.000000 .
H3 H -1.22363(18) -0.20523(15) -0.98915(7) 0.0249(4) Uiso 1.000000 R
C4 C -1.06888(18) -0.08439(15) -0.86462(7) 0.0194(3) Uani 1.000000 .
C5 C -0.82710(19) -0.01463(16) -0.77975(7) 0.0217(3) Uani 1.000000 .
H5 H -0.89224(19) 0.04950(16) -0.74776(7) 0.0260(4) Uiso 1.000000 R
C6 C -0.7908(2) -0.16224(17) -0.74525(7) 0.0248(3) Uani 1.000000 .
H6 H -0.9001(2) -0.20712(17) -0.73229(7) 0.0298(4) Uiso 1.000000 R
C7 C -0.6916(2) -0.1392(2) -0.67907(8) 0.0398(4) Uani 1.000000 .
H7a H -0.5798(6) -0.1037(13) -0.69047(9) 0.0597(7) Uiso 1.000000 GR
H7b H -0.7483(9) -0.0666(10) -0.6501(3) 0.0597(7) Uiso 1.000000 GR
H7c H -0.6831(13) -0.2326(4) -0.6542(3) 0.0597(7) Uiso 1.000000 GR
C8 C -0.7028(2) -0.26889(17) -0.79328(8) 0.0304(4) Uani 1.000000 .
H8a H -0.5916(6) -0.2312(7) -0.8042(5) 0.0457(6) Uiso 1.000000 GR
H8b H -0.6928(13) -0.3649(4) -0.7708(3) 0.0457(6) Uiso 1.000000 GR
H8c H -0.7673(8) -0.2793(10) -0.8358(3) 0.0457(6) Uiso 1.000000 GR
C9 C -0.81487(17) -0.00460(15) -0.90034(7) 0.0203(3) Uani 1.000000 .
C10 C -0.6740(2) 0.07009(17) -0.80729(8) 0.0267(4) Uani 1.000000 .
H10a H -0.5718(2) 0.03694(17) -0.78338(8) 0.0320(4) Uiso 1.000000 R
H10b H -0.6878(2) 0.17683(17) -0.79917(8) 0.0320(4) Uiso 1.000000 R
C11 C -0.90227(18) -0.03777(16) -0.95671(7) 0.0198(3) Uani 1.000000 .
C12 C -1.04084(18) -0.10671(18) -1.05168(8) 0.0256(3) Uani 1.000000 .
H12a H -1.08609(18) -0.05380(18) -1.09211(8) 0.0307(4) Uiso 1.000000 R
H12b H -1.01464(18) -0.20881(18) -1.06561(8) 0.0307(4) Uiso 1.000000 R
C13 C -1.4238(2) -0.0128(2) -1.05404(9) 0.0355(4) Uani 1.000000 .
H13a H -1.3672(5) 0.0046(13) -1.09799(9) 0.0533(6) Uiso 1.000000 GR
H13b H -1.4634(12) -0.1147(4) -1.0523(4) 0.0533(6) Uiso 1.000000 GR
H13c H -1.5187(8) 0.0542(10) -1.0498(4) 0.0533(6) Uiso 1.000000 GR
B1 B -1.2217(2) -0.1368(2) -0.81847(10) 0.0262(4) Uani 1.000000 .
H1d H -1.189(2) -0.1225(19) -0.7637(9) 0.036(5) Uiso 1.000000 .
H1e H -1.330(3) -0.064(2) -0.8327(10) 0.067(7) Uiso 1.000000 .
H1f H -1.251(3) -0.259(2) -0.8318(10) 0.061(6) Uiso 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3524(17) . ?
O1 C10 1.4640(18) . ?
O2 C11 1.3564(16) . ?
O2 C12 1.4680(18) . ?
N1 C3 1.4687(17) . ?
N1 C4 1.3535(19) . ?
N1 C11 1.3757(18) . ?
N2 C4 1.3508(18) . ?
N2 C5 1.4758(18) . ?
N2 C9 1.3802(17) . ?
C1 H1a 0.9800 . ?
C1 H1b 0.9800 . ?
C1 H1c 0.9800 . ?
C1 C2 1.526(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.5333(19) . ?
C2 C13 1.529(2) . ?
C3 H3 1.0000 . ?
C3 C12 1.544(2) . ?
C4 B1 1.593(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.529(2) . ?
C5 C10 1.546(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.527(2) . ?
C6 C8 1.520(2) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
C9 C11 1.335(2) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
B1 H1d 1.104(17) . ?
B1 H1e 1.13(2) . ?
B1 H1f 1.16(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C9 105.13(11) . . ?
C12 O2 C11 105.12(11) . . ?
C4 N1 C3 136.04(12) . . ?
C11 N1 C3 110.53(11) . . ?
C11 N1 C4 112.81(12) . . ?
C5 N2 C4 136.40(12) . . ?
C9 N2 C4 112.70(11) . . ?
C9 N2 C5 110.40(11) . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C2 C1 H1a 109.5 . . ?
C2 C1 H1b 109.5 . . ?
C2 C1 H1c 109.5 . . ?
H2 C2 C1 107.39(10) . . ?
C3 C2 C1 112.31(12) . . ?
C3 C2 H2 107.39(8) . . ?
C13 C2 C1 111.41(13) . . ?
C13 C2 H2 107.39(9) . . ?
C13 C2 C3 110.68(12) . . ?
C2 C3 N1 111.40(11) . . ?
H3 C3 N1 109.83(7) . . ?
H3 C3 C2 109.83(7) . . ?
C12 C3 N1 99.17(10) . . ?
C12 C3 C2 116.30(12) . . ?
C12 C3 H3 109.83(8) . . ?
N2 C4 N1 102.11(12) . . ?
B1 C4 N1 128.35(14) . . ?
B1 C4 N2 129.50(14) . . ?
H5 C5 N2 109.87(7) . . ?
C6 C5 N2 111.95(11) . . ?
C6 C5 H5 109.87(8) . . ?
C10 C5 N2 98.78(11) . . ?
C10 C5 H5 109.87(8) . . ?
C10 C5 C6 115.98(13) . . ?
H6 C6 C5 107.57(8) . . ?
C7 C6 C5 110.36(13) . . ?
C7 C6 H6 107.57(9) . . ?
C8 C6 C5 112.36(12) . . ?
C8 C6 H6 107.57(9) . . ?
C8 C6 C7 111.19(14) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C6 109.5 . . ?
H8b C8 C6 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C6 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
N2 C9 O1 113.08(11) . . ?
C11 C9 O1 140.69(13) . . ?
C11 C9 N2 106.15(12) . . ?
C5 C10 O1 107.65(12) . . ?
H10a C10 O1 110.18(8) . . ?
H10a C10 C5 110.18(8) . . ?
H10b C10 O1 110.18(7) . . ?
H10b C10 C5 110.18(8) . . ?
H10b C10 H10a 108.5 . . ?
N1 C11 O2 113.09(12) . . ?
C9 C11 O2 140.60(14) . . ?
C9 C11 N1 106.22(12) . . ?
C3 C12 O2 107.43(11) . . ?
H12a C12 O2 110.23(8) . . ?
H12a C12 C3 110.23(8) . . ?
H12b C12 O2 110.23(8) . . ?
H12b C12 C3 110.23(8) . . ?
H12b C12 H12a 108.5 . . ?
H13a C13 C2 109.5 . . ?
H13b C13 C2 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C2 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H1d B1 C4 108.7(10) . . ?
H1e B1 C4 106.2(11) . . ?
H1e B1 H1d 110.6(14) . . ?
H1f B1 C4 108.6(11) . . ?
H1f B1 H1d 112.1(13) . . ?
H1f B1 H1e 110.4(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rm1552
_database_code_depnum_ccdc_archive 'CCDC 1482175'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H43 B N2'
_chemical_formula_sum            'C23 H43 B N2'
_chemical_formula_weight         358.44
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           ' P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z

_symmetry_Int_Tables_number      1
_cell_length_a                   9.4015(3)
_cell_length_b                   9.5499(3)
_cell_length_c                   12.9102(4)
_cell_angle_alpha                91.586(2)
_cell_angle_beta                 109.357(3)
_cell_angle_gamma                93.844(3)
_cell_volume                     1089.60(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8401
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.118
_cell_measurement_theta_min      4.067
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
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_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.0924
_exptl_crystal_description       block
_exptl_crystal_F_000             400.1232
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18560
_diffrn_reflns_theta_full        29.8735
_diffrn_reflns_theta_max         29.87
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_temperature      150.15
_diffrn_measured_fraction_theta_full 0.8116
_diffrn_measured_fraction_theta_max 0.8095
_diffrn_measurement_device_type  'Supernova Dual Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.757
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                8977
_reflns_number_total             10164
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_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    SHELXS
_refine_diff_density_max         0.2503
_refine_diff_density_min         -0.1856
_refine_diff_density_rms         0.0457
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0(3)
_refine_ls_d_res_high            0.7135
_refine_ls_d_res_low             6.0816
_refine_ls_goodness_of_fit_ref   1.0711
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    128
_refine_ls_number_parameters     483
_refine_ls_number_reflns         10164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      1.0711
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+0.2889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1254
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1(3) 0(3)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C11(H11), C14(H14), C17(H17), C32(H32), C33(H33),
 C37(H37), C41(H41), C44(H44), C47(H47)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b), C6(H6a,H6b), C8(H8a,H8b), C9(H9a,H9b), C10(H10a,
 H10b), C18(H18a,H18b), C19(H19a,H19b), C34(H34a,H34b), C35(H35a,H35b),
 C36(H36a,H36b), C38(H38a,H38b), C39(H39a,H39b), C40(H40a,H40b), C48(H48a,H48b),
  C49(H49a,H49b)
3.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c), C16(H16a,H16b,
 H16c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c), C24(H24a,H24b,H24c), C42(H42a,
 H42b,H42c), C43(H43a,H43b,H43c), C45(H45a,H45b,H45c), C46(H46a,H46b,H46c),
 C52(H52a,H52b,H52c), C53(H53a,H53b,H53c), C54(H54a,H54b,H54c)
;
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_refinement_flags_posn
N1 N 0.64837(18) -0.03235(16) 0.91955(13) 0.0240(3) Uani 1.000000 .
B1 B 0.6358(2) 0.0998(2) 0.87385(16) 0.0218(4) Uani 1.000000 .
N2 N 0.92748(18) 0.19344(18) 0.91257(14) 0.0285(4) Uani 1.000000 .
C2 C 0.7647(2) 0.2024(2) 0.85844(15) 0.0236(4) Uani 1.000000 .
H2 H 0.7476(2) 0.2936(2) 0.89066(15) 0.0283(5) Uiso 1.000000 R
C3 C 0.7156(2) 0.2306(2) 0.73041(16) 0.0292(4) Uani 1.000000 .
H3 H 0.8123(2) 0.2393(2) 0.71374(16) 0.0351(5) Uiso 1.000000 R
N3 N 0.88566(17) 0.44730(16) 0.43676(12) 0.0220(3) Uani 1.000000 .
C4 C 0.6162(3) 0.1095(2) 0.65004(16) 0.0333(5) Uani 1.000000 .
H4a H 0.6395(3) 0.1140(2) 0.58078(16) 0.0399(6) Uiso 1.000000 R
H4b H 0.6498(3) 0.0195(2) 0.68224(16) 0.0399(6) Uiso 1.000000 R
N4 N 0.67643(19) 0.71911(16) 0.40130(14) 0.0272(4) Uani 1.000000 .
C5 C 0.4456(3) 0.1028(2) 0.62007(17) 0.0357(5) Uani 1.000000 .
H5a H 0.4103(3) 0.1904(2) 0.58442(17) 0.0429(6) Uiso 1.000000 R
H5b H 0.4014(3) 0.0240(2) 0.56471(17) 0.0429(6) Uiso 1.000000 R
C6 C 0.3818(2) 0.0838(2) 0.71390(18) 0.0343(5) Uani 1.000000 .
H6a H 0.2781(2) 0.1150(2) 0.68977(18) 0.0411(6) Uiso 1.000000 R
H6b H 0.3736(2) -0.0178(2) 0.72628(18) 0.0411(6) Uiso 1.000000 R
C7 C 0.4727(2) 0.1624(2) 0.82529(16) 0.0253(4) Uani 1.000000 .
H7 H 0.4176(2) 0.1342(2) 0.87669(16) 0.0303(5) Uiso 1.000000 R
C8 C 0.4691(2) 0.3239(2) 0.82143(18) 0.0313(4) Uani 1.000000 .
H8a H 0.3681(2) 0.3476(2) 0.82118(18) 0.0376(5) Uiso 1.000000 R
H8b H 0.5438(2) 0.3661(2) 0.89062(18) 0.0376(5) Uiso 1.000000 R
C9 C 0.5005(3) 0.3963(2) 0.72561(18) 0.0344(5) Uani 1.000000 .
H9a H 0.4167(3) 0.3651(2) 0.65736(18) 0.0413(6) Uiso 1.000000 R
H9b H 0.4963(3) 0.4987(2) 0.73712(18) 0.0413(6) Uiso 1.000000 R
C10 C 0.6499(3) 0.3735(2) 0.70575(17) 0.0341(5) Uani 1.000000 .
H10a H 0.7270(3) 0.4466(2) 0.75059(17) 0.0409(6) Uiso 1.000000 R
H10b H 0.6350(3) 0.3902(2) 0.62766(17) 0.0409(6) Uiso 1.000000 R
C11 C 0.5178(2) -0.1156(2) 0.93352(18) 0.0305(4) Uani 1.000000 .
H11 H 0.4273(2) -0.0615(2) 0.90130(18) 0.0366(5) Uiso 1.000000 R
C12 C 0.5368(3) -0.1287(2) 1.05509(19) 0.0403(5) Uani 1.000000 .
H12a H 0.6250(13) -0.1809(17) 1.0902(4) 0.0605(8) Uiso 1.000000 GR
H12b H 0.552(2) -0.0347(2) 1.0913(4) 0.0605(8) Uiso 1.000000 GR
H12c H 0.4461(9) -0.1788(17) 1.06170(19) 0.0605(8) Uiso 1.000000 GR
C13 C 0.4829(3) -0.2591(2) 0.8716(2) 0.0435(6) Uani 1.000000 .
H13a H 0.473(2) -0.2474(3) 0.7944(4) 0.0652(9) Uiso 1.000000 GR
H13b H 0.5653(11) -0.3187(7) 0.9048(10) 0.0652(9) Uiso 1.000000 GR
H13c H 0.3881(11) -0.3034(9) 0.8759(13) 0.0652(9) Uiso 1.000000 GR
C14 C 1.0156(2) 0.3238(2) 0.96794(17) 0.0315(4) Uani 1.000000 .
H14 H 1.1089(2) 0.2944(2) 1.02432(17) 0.0378(5) Uiso 1.000000 R
C15 C 0.9412(3) 0.4184(2) 1.02949(19) 0.0379(5) Uani 1.000000 .
H15a H 0.8619(14) 0.4663(14) 0.9763(2) 0.0569(8) Uiso 1.000000 GR
H15b H 0.8966(17) 0.3610(3) 1.0744(11) 0.0569(8) Uiso 1.000000 GR
H15c H 1.0176(5) 0.4883(12) 1.0771(11) 0.0569(8) Uiso 1.000000 GR
C16 C 1.0694(3) 0.4141(3) 0.8891(2) 0.0483(6) Uani 1.000000 .
H16a H 1.122(2) 0.3564(6) 0.8513(12) 0.0724(10) Uiso 1.000000 GR
H16b H 0.9819(4) 0.4507(18) 0.8347(10) 0.0724(10) Uiso 1.000000 GR
H16c H 1.1390(18) 0.4927(12) 0.9309(3) 0.0724(10) Uiso 1.000000 GR
C17 C 0.7872(2) -0.1091(2) 0.94976(16) 0.0281(4) Uani 1.000000 .
H17 H 0.7701(2) -0.1935(2) 0.98957(16) 0.0337(5) Uiso 1.000000 R
C18 C 0.8223(3) -0.1595(2) 0.84744(18) 0.0334(5) Uani 1.000000 .
H18a H 0.8684(3) -0.2505(2) 0.85929(18) 0.0400(6) Uiso 1.000000 R
H18b H 0.7288(3) -0.1712(2) 0.78255(18) 0.0400(6) Uiso 1.000000 R
C19 C 0.9336(2) -0.0444(2) 0.83072(18) 0.0350(5) Uani 1.000000 .
H19a H 1.0199(2) -0.0873(2) 0.81812(18) 0.0420(6) Uiso 1.000000 R
H19b H 0.8825(2) 0.0087(2) 0.76580(18) 0.0420(6) Uiso 1.000000 R
C20 C 0.9912(2) 0.0563(2) 0.93618(17) 0.0309(4) Uani 1.000000 .
C21 C 0.9355(2) -0.0263(2) 1.02125(16) 0.0306(4) Uani 1.000000 .
C22 C 1.0450(3) -0.1375(3) 1.0767(2) 0.0458(6) Uani 1.000000 .
H22a H 1.1405(8) -0.0900(3) 1.1251(13) 0.0687(9) Uiso 1.000000 GR
H22b H 0.9993(10) -0.1967(13) 1.1200(13) 0.0687(9) Uiso 1.000000 GR
H22c H 1.0643(18) -0.1962(14) 1.0201(2) 0.0687(9) Uiso 1.000000 GR
C23 C 0.9179(3) 0.0682(2) 1.11288(16) 0.0338(5) Uani 1.000000 .
H23a H 0.8413(14) 0.1340(12) 1.0810(2) 0.0507(7) Uiso 1.000000 GR
H23b H 0.8862(18) 0.0104(3) 1.1641(8) 0.0507(7) Uiso 1.000000 GR
H23c H 1.0148(5) 0.1210(13) 1.1523(9) 0.0507(7) Uiso 1.000000 GR
C24 C 1.1651(3) 0.0759(3) 0.9718(2) 0.0468(6) Uani 1.000000 .
H24a H 1.1947(3) 0.1383(17) 0.9222(10) 0.0702(9) Uiso 1.000000 GR
H24b H 1.2058(3) 0.1173(19) 1.0471(6) 0.0702(9) Uiso 1.000000 GR
H24c H 1.2053(3) -0.0156(4) 0.9688(16) 0.0702(9) Uiso 1.000000 GR
B31 B 0.7282(2) 0.4437(2) 0.38990(16) 0.0198(4) Uani 1.000000 .
C32 C 0.6273(2) 0.57334(18) 0.36120(14) 0.0209(4) Uani 1.000000 .
H32 H 0.5487(2) 0.54952(18) 0.39591(14) 0.0251(4) Uiso 1.000000 R
C33 C 0.5319(2) 0.5539(2) 0.23378(16) 0.0286(4) Uani 1.000000 .
H33 H 0.5222(2) 0.6516(2) 0.20766(16) 0.0344(5) Uiso 1.000000 R
C34 C 0.6073(3) 0.4782(2) 0.16037(16) 0.0331(5) Uani 1.000000 .
H34a H 0.5714(3) 0.5176(2) 0.08686(16) 0.0397(6) Uiso 1.000000 R
H34b H 0.7176(3) 0.5039(2) 0.19148(16) 0.0397(6) Uiso 1.000000 R
C35 C 0.5841(3) 0.3188(2) 0.14374(17) 0.0376(5) Uani 1.000000 .
H35a H 0.4748(3) 0.2930(2) 0.10670(17) 0.0451(6) Uiso 1.000000 R
H35b H 0.6368(3) 0.2895(2) 0.09280(17) 0.0451(6) Uiso 1.000000 R
C36 C 0.6378(2) 0.2331(2) 0.24648(16) 0.0297(4) Uani 1.000000 .
H36a H 0.5789(2) 0.1404(2) 0.22993(16) 0.0357(5) Uiso 1.000000 R
H36b H 0.7450(2) 0.2160(2) 0.25972(16) 0.0357(5) Uiso 1.000000 R
C37 C 0.6259(2) 0.29686(18) 0.35490(15) 0.0229(4) Uani 1.000000 .
H37 H 0.6754(2) 0.23129(18) 0.41268(15) 0.0274(5) Uiso 1.000000 R
C38 C 0.4609(2) 0.2956(2) 0.35330(16) 0.0284(4) Uani 1.000000 .
H38a H 0.4274(2) 0.1985(2) 0.36466(16) 0.0340(5) Uiso 1.000000 R
H38b H 0.4600(2) 0.3554(2) 0.41691(16) 0.0340(5) Uiso 1.000000 R
C39 C 0.3438(2) 0.3451(2) 0.24984(18) 0.0351(5) Uani 1.000000 .
H39a H 0.3372(2) 0.2788(2) 0.18778(18) 0.0421(6) Uiso 1.000000 R
H39b H 0.2442(2) 0.3369(2) 0.26066(18) 0.0421(6) Uiso 1.000000 R
C40 C 0.3688(2) 0.4942(2) 0.21486(18) 0.0373(5) Uani 1.000000 .
H40a H 0.3232(2) 0.5586(2) 0.25405(18) 0.0447(6) Uiso 1.000000 R
H40b H 0.3115(2) 0.4967(2) 0.13540(18) 0.0447(6) Uiso 1.000000 R
C41 C 0.9649(2) 0.3175(2) 0.46680(18) 0.0315(5) Uani 1.000000 .
H41 H 0.8860(2) 0.2368(2) 0.44189(18) 0.0378(5) Uiso 1.000000 R
C42 C 1.0793(3) 0.2960(3) 0.4083(2) 0.0451(6) Uani 1.000000 .
H42a H 1.0291(6) 0.298(2) 0.3287(2) 0.0677(9) Uiso 1.000000 GR
H42b H 1.1613(11) 0.3711(12) 0.4329(12) 0.0677(9) Uiso 1.000000 GR
H42c H 1.1210(16) 0.2048(9) 0.4259(13) 0.0677(9) Uiso 1.000000 GR
C43 C 1.0350(3) 0.3125(3) 0.5907(2) 0.0453(6) Uani 1.000000 .
H43a H 1.1206(14) 0.3839(14) 0.6178(3) 0.0680(9) Uiso 1.000000 GR
H43b H 0.9592(7) 0.331(2) 0.6252(2) 0.0680(9) Uiso 1.000000 GR
H43c H 1.071(2) 0.2193(7) 0.6093(2) 0.0680(9) Uiso 1.000000 GR
C44 C 0.5749(2) 0.7944(2) 0.44441(17) 0.0304(4) Uani 1.000000 .
H44 H 0.6383(2) 0.8742(2) 0.49355(17) 0.0365(5) Uiso 1.000000 R
C45 C 0.4985(3) 0.7100(2) 0.51370(19) 0.0369(5) Uani 1.000000 .
H45a H 0.4173(13) 0.6446(13) 0.4654(2) 0.0553(8) Uiso 1.000000 GR
H45b H 0.5734(5) 0.6570(14) 0.5661(10) 0.0553(8) Uiso 1.000000 GR
H45c H 0.4560(17) 0.7744(3) 0.5539(11) 0.0553(8) Uiso 1.000000 GR
C46 C 0.4523(3) 0.8603(3) 0.3521(2) 0.0444(6) Uani 1.000000 .
H46a H 0.5005(3) 0.9219(16) 0.3118(10) 0.0666(9) Uiso 1.000000 GR
H46b H 0.3870(14) 0.7856(3) 0.3016(9) 0.0666(9) Uiso 1.000000 GR
H46c H 0.3913(14) 0.9151(17) 0.3842(3) 0.0666(9) Uiso 1.000000 GR
C47 C 0.9909(2) 0.5748(2) 0.45791(16) 0.0253(4) Uani 1.000000 .
H47 H 1.0941(2) 0.5494(2) 0.50230(16) 0.0304(5) Uiso 1.000000 R
C48 C 0.9990(2) 0.6355(2) 0.35031(17) 0.0322(5) Uani 1.000000 .
H48a H 1.1017(2) 0.6795(2) 0.36116(17) 0.0387(5) Uiso 1.000000 R
H48b H 0.9741(2) 0.5605(2) 0.29112(17) 0.0387(5) Uiso 1.000000 R
C49 C 0.8831(3) 0.7448(2) 0.32117(18) 0.0335(5) Uani 1.000000 .
H49a H 0.9279(3) 0.8323(2) 0.30106(18) 0.0402(6) Uiso 1.000000 R
H49b H 0.7941(3) 0.7091(2) 0.25764(18) 0.0402(6) Uiso 1.000000 R
C50 C 0.8338(2) 0.77533(19) 0.42356(17) 0.0291(4) Uani 1.000000 .
C51 C 0.9516(2) 0.7013(2) 0.51777(16) 0.0287(4) Uani 1.000000 .
C52 C 1.1009(3) 0.7944(3) 0.5701(2) 0.0469(6) Uani 1.000000 .
H52a H 1.0828(6) 0.8749(12) 0.6114(14) 0.0704(9) Uiso 1.000000 GR
H52b H 1.1764(8) 0.7392(6) 0.6199(13) 0.0704(9) Uiso 1.000000 GR
H52c H 1.1383(12) 0.8281(17) 0.5121(2) 0.0704(9) Uiso 1.000000 GR
C53 C 0.8940(3) 0.6608(2) 0.61112(17) 0.0336(5) Uani 1.000000 .
H53a H 0.8090(12) 0.5890(13) 0.5836(4) 0.0504(7) Uiso 1.000000 GR
H53b H 0.9756(6) 0.6234(16) 0.6701(6) 0.0504(7) Uiso 1.000000 GR
H53c H 0.8605(17) 0.7439(4) 0.6397(9) 0.0504(7) Uiso 1.000000 GR
C54 C 0.8477(3) 0.9365(2) 0.4463(2) 0.0464(6) Uani 1.000000 .
H54a H 0.7646(13) 0.9777(3) 0.3912(10) 0.0697(9) Uiso 1.000000 GR
H54b H 0.843(2) 0.9576(2) 0.5197(7) 0.0697(9) Uiso 1.000000 GR
H54c H 0.9445(10) 0.9764(3) 0.4423(16) 0.0697(9) Uiso 1.000000 GR


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
N1 B1 1.403(3) . ?
N1 C11 1.482(3) . ?
N1 C17 1.483(2) . ?
B1 C2 1.575(3) . ?
B1 C7 1.615(3) . ?
N2 C2 1.466(2) . ?
N2 C14 1.472(3) . ?
N2 C20 1.474(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.598(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.560(3) . ?
C3 C10 1.534(3) . ?
N3 B31 1.399(3) . ?
N3 C41 1.483(2) . ?
N3 C47 1.476(2) . ?
C4 H4a 0.9900 . ?
C4 H4b 0.9900 . ?
C4 C5 1.517(3) . ?
N4 C32 1.461(2) . ?
N4 C44 1.470(3) . ?
N4 C50 1.470(3) . ?
C5 H5a 0.9900 . ?
C5 H5b 0.9900 . ?
C5 C6 1.529(3) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C6 C7 1.549(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.547(3) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.536(3) . ?
C9 H9a 0.9900 . ?
C9 H9b 0.9900 . ?
C9 C10 1.537(3) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C11 H11 1.0000 . ?
C11 C12 1.529(3) . ?
C11 C13 1.527(3) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.533(3) . ?
C14 C16 1.539(3) . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C17 H17 1.0000 . ?
C17 C18 1.536(3) . ?
C17 C21 1.543(3) . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C18 C19 1.535(3) . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.563(3) . ?
C20 C21 1.574(3) . ?
C20 C24 1.541(3) . ?
C21 C22 1.549(3) . ?
C21 C23 1.527(3) . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?
C23 H23a 0.9800 . ?
C23 H23b 0.9800 . ?
C23 H23c 0.9800 . ?
C24 H24a 0.9800 . ?
C24 H24b 0.9800 . ?
C24 H24c 0.9800 . ?
B31 C32 1.587(3) . ?
B31 C37 1.610(3) . ?
C32 H32 1.0000 . ?
C32 C33 1.590(3) . ?
C33 H33 1.0000 . ?
C33 C34 1.549(3) . ?
C33 C40 1.537(3) . ?
C34 H34a 0.9900 . ?
C34 H34b 0.9900 . ?
C34 C35 1.522(3) . ?
C35 H35a 0.9900 . ?
C35 H35b 0.9900 . ?
C35 C36 1.535(3) . ?
C36 H36a 0.9900 . ?
C36 H36b 0.9900 . ?
C36 C37 1.552(3) . ?
C37 H37 1.0000 . ?
C37 C38 1.543(3) . ?
C38 H38a 0.9900 . ?
C38 H38b 0.9900 . ?
C38 C39 1.533(3) . ?
C39 H39a 0.9900 . ?
C39 H39b 0.9900 . ?
C39 C40 1.532(3) . ?
C40 H40a 0.9900 . ?
C40 H40b 0.9900 . ?
C41 H41 1.0000 . ?
C41 C42 1.527(3) . ?
C41 C43 1.519(3) . ?
C42 H42a 0.9800 . ?
C42 H42b 0.9800 . ?
C42 H42c 0.9800 . ?
C43 H43a 0.9800 . ?
C43 H43b 0.9800 . ?
C43 H43c 0.9800 . ?
C44 H44 1.0000 . ?
C44 C45 1.534(3) . ?
C44 C46 1.540(3) . ?
C45 H45a 0.9800 . ?
C45 H45b 0.9800 . ?
C45 H45c 0.9800 . ?
C46 H46a 0.9800 . ?
C46 H46b 0.9800 . ?
C46 H46c 0.9800 . ?
C47 H47 1.0000 . ?
C47 C48 1.543(3) . ?
C47 C51 1.546(3) . ?
C48 H48a 0.9900 . ?
C48 H48b 0.9900 . ?
C48 C49 1.524(3) . ?
C49 H49a 0.9900 . ?
C49 H49b 0.9900 . ?
C49 C50 1.565(3) . ?
C50 C51 1.570(3) . ?
C50 C54 1.548(3) . ?
C51 C52 1.546(3) . ?
C51 C53 1.525(3) . ?
C52 H52a 0.9800 . ?
C52 H52b 0.9800 . ?
C52 H52c 0.9800 . ?
C53 H53a 0.9800 . ?
C53 H53b 0.9800 . ?
C53 H53c 0.9800 . ?
C54 H54a 0.9800 . ?
C54 H54b 0.9800 . ?
C54 H54c 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
C11 N1 B1 122.55(16) . . ?
C17 N1 B1 124.57(16) . . ?
C17 N1 C11 112.68(15) . . ?
C2 B1 N1 128.26(17) . . ?
C7 B1 N1 120.40(17) . . ?
C7 B1 C2 111.31(16) . . ?
C14 N2 C2 116.42(16) . . ?
C20 N2 C2 120.99(16) . . ?
C20 N2 C14 120.58(16) . . ?
N2 C2 B1 125.42(16) . . ?
H2 C2 B1 102.19(10) . . ?
H2 C2 N2 102.19(10) . . ?
C3 C2 B1 106.65(15) . . ?
C3 C2 N2 114.69(16) . . ?
C3 C2 H2 102.19(10) . . ?
H3 C3 C2 105.06(10) . . ?
C4 C3 C2 116.22(16) . . ?
C4 C3 H3 105.06(11) . . ?
C10 C3 C2 111.77(16) . . ?
C10 C3 H3 105.06(11) . . ?
C10 C3 C4 112.49(17) . . ?
C41 N3 B31 121.91(16) . . ?
C47 N3 B31 125.39(15) . . ?
C47 N3 C41 112.66(15) . . ?
H4a C4 C3 107.48(11) . . ?
H4b C4 C3 107.48(11) . . ?
H4b C4 H4a 107.0 . . ?
C5 C4 C3 119.37(18) . . ?
C5 C4 H4a 107.48(11) . . ?
C5 C4 H4b 107.48(12) . . ?
C44 N4 C32 116.60(15) . . ?
C50 N4 C32 121.07(15) . . ?
C50 N4 C44 120.56(15) . . ?
H5a C5 C4 108.07(12) . . ?
H5b C5 C4 108.07(11) . . ?
H5b C5 H5a 107.3 . . ?
C6 C5 C4 116.91(17) . . ?
C6 C5 H5a 108.07(11) . . ?
C6 C5 H5b 108.07(11) . . ?
H6a C6 C5 108.15(11) . . ?
H6b C6 C5 108.15(11) . . ?
H6b C6 H6a 107.3 . . ?
C7 C6 C5 116.55(17) . . ?
C7 C6 H6a 108.15(11) . . ?
C7 C6 H6b 108.15(10) . . ?
C6 C7 B1 109.20(16) . . ?
H7 C7 B1 105.24(10) . . ?
H7 C7 C6 105.24(11) . . ?
C8 C7 B1 117.68(16) . . ?
C8 C7 C6 113.09(16) . . ?
C8 C7 H7 105.24(11) . . ?
H8a C8 C7 107.69(11) . . ?
H8b C8 C7 107.69(11) . . ?
H8b C8 H8a 107.1 . . ?
C9 C8 C7 118.51(17) . . ?
C9 C8 H8a 107.69(11) . . ?
C9 C8 H8b 107.69(12) . . ?
H9a C9 C8 107.74(12) . . ?
H9b C9 C8 107.74(11) . . ?
H9b C9 H9a 107.1 . . ?
C10 C9 C8 118.30(17) . . ?
C10 C9 H9a 107.74(12) . . ?
C10 C9 H9b 107.74(11) . . ?
C9 C10 C3 118.30(17) . . ?
H10a C10 C3 107.74(11) . . ?
H10a C10 C9 107.74(12) . . ?
H10b C10 C3 107.74(11) . . ?
H10b C10 C9 107.74(11) . . ?
H10b C10 H10a 107.1 . . ?
H11 C11 N1 106.71(10) . . ?
C12 C11 N1 111.35(18) . . ?
C12 C11 H11 106.71(12) . . ?
C13 C11 N1 113.47(18) . . ?
C13 C11 H11 106.71(13) . . ?
C13 C11 C12 111.43(18) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14 C14 N2 106.28(11) . . ?
C15 C14 N2 116.99(17) . . ?
C15 C14 H14 106.28(12) . . ?
C16 C14 N2 112.09(17) . . ?
C16 C14 H14 106.28(13) . . ?
C16 C14 C15 108.2(2) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16a C16 C14 109.5 . . ?
H16b C16 C14 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 C14 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17 C17 N1 108.19(10) . . ?
C18 C17 N1 111.46(16) . . ?
C18 C17 H17 108.19(11) . . ?
C21 C17 N1 116.77(16) . . ?
C21 C17 H17 108.19(11) . . ?
C21 C17 C18 103.70(17) . . ?
H18a C18 C17 110.64(11) . . ?
H18b C18 C17 110.64(11) . . ?
H18b C18 H18a 108.8 . . ?
C19 C18 C17 105.49(17) . . ?
C19 C18 H18a 110.64(11) . . ?
C19 C18 H18b 110.64(12) . . ?
H19a C19 C18 110.03(11) . . ?
H19b C19 C18 110.03(12) . . ?
H19b C19 H19a 108.4 . . ?
C20 C19 C18 108.31(17) . . ?
C20 C19 H19a 110.03(11) . . ?
C20 C19 H19b 110.03(12) . . ?
C19 C20 N2 110.20(17) . . ?
C21 C20 N2 113.40(16) . . ?
C21 C20 C19 103.02(17) . . ?
C24 C20 N2 109.80(18) . . ?
C24 C20 C19 107.90(17) . . ?
C24 C20 C21 112.20(18) . . ?
C20 C21 C17 104.08(16) . . ?
C22 C21 C17 106.21(18) . . ?
C22 C21 C20 111.64(18) . . ?
C23 C21 C17 113.90(17) . . ?
C23 C21 C20 113.53(17) . . ?
C23 C21 C22 107.31(17) . . ?
H22a C22 C21 109.5 . . ?
H22b C22 C21 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C21 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
H23a C23 C21 109.5 . . ?
H23b C23 C21 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C21 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
H24a C24 C20 109.5 . . ?
H24b C24 C20 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C20 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?
C32 B31 N3 127.63(17) . . ?
C37 B31 N3 121.15(16) . . ?
C37 B31 C32 111.20(16) . . ?
B31 C32 N4 125.87(16) . . ?
H32 C32 N4 102.09(10) . . ?
H32 C32 B31 102.09(10) . . ?
C33 C32 N4 114.48(15) . . ?
C33 C32 B31 106.60(14) . . ?
C33 C32 H32 102.09(10) . . ?
H33 C33 C32 104.93(9) . . ?
C34 C33 C32 116.24(16) . . ?
C34 C33 H33 104.93(11) . . ?
C40 C33 C32 111.45(16) . . ?
C40 C33 H33 104.93(11) . . ?
C40 C33 C34 113.11(18) . . ?
H34a C34 C33 107.53(10) . . ?
H34b C34 C33 107.53(11) . . ?
H34b C34 H34a 107.0 . . ?
C35 C34 C33 119.16(18) . . ?
C35 C34 H34a 107.53(11) . . ?
C35 C34 H34b 107.53(13) . . ?
H35a C35 C34 107.96(13) . . ?
H35b C35 C34 107.96(11) . . ?
H35b C35 H35a 107.2 . . ?
C36 C35 C34 117.37(17) . . ?
C36 C35 H35a 107.96(12) . . ?
C36 C35 H35b 107.96(12) . . ?
H36a C36 C35 107.94(12) . . ?
H36b C36 C35 107.94(12) . . ?
H36b C36 H36a 107.2 . . ?
C37 C36 C35 117.46(16) . . ?
C37 C36 H36a 107.94(10) . . ?
C37 C36 H36b 107.94(11) . . ?
C36 C37 B31 110.10(15) . . ?
H37 C37 B31 105.32(10) . . ?
H37 C37 C36 105.32(10) . . ?
C38 C37 B31 117.08(15) . . ?
C38 C37 C36 112.61(16) . . ?
C38 C37 H37 105.32(10) . . ?
H38a C38 C37 107.99(10) . . ?
H38b C38 C37 107.99(10) . . ?
H38b C38 H38a 107.2 . . ?
C39 C38 C37 117.24(17) . . ?
C39 C38 H38a 107.99(11) . . ?
C39 C38 H38b 107.99(12) . . ?
H39a C39 C38 107.73(12) . . ?
H39b C39 C38 107.73(11) . . ?
H39b C39 H39a 107.1 . . ?
C40 C39 C38 118.31(17) . . ?
C40 C39 H39a 107.73(12) . . ?
C40 C39 H39b 107.73(12) . . ?
C39 C40 C33 118.24(18) . . ?
H40a C40 C33 107.75(12) . . ?
H40a C40 C39 107.75(13) . . ?
H40b C40 C33 107.75(11) . . ?
H40b C40 C39 107.75(11) . . ?
H40b C40 H40a 107.1 . . ?
H41 C41 N3 106.76(11) . . ?
C42 C41 N3 113.09(18) . . ?
C42 C41 H41 106.76(13) . . ?
C43 C41 N3 110.91(18) . . ?
C43 C41 H41 106.76(13) . . ?
C43 C41 C42 112.12(19) . . ?
H42a C42 C41 109.5 . . ?
H42b C42 C41 109.5 . . ?
H42b C42 H42a 109.5 . . ?
H42c C42 C41 109.5 . . ?
H42c C42 H42a 109.5 . . ?
H42c C42 H42b 109.5 . . ?
H43a C43 C41 109.5 . . ?
H43b C43 C41 109.5 . . ?
H43b C43 H43a 109.5 . . ?
H43c C43 C41 109.5 . . ?
H43c C43 H43a 109.5 . . ?
H43c C43 H43b 109.5 . . ?
H44 C44 N4 106.54(11) . . ?
C45 C44 N4 116.21(16) . . ?
C45 C44 H44 106.54(12) . . ?
C46 C44 N4 111.65(17) . . ?
C46 C44 H44 106.54(12) . . ?
C46 C44 C45 108.79(19) . . ?
H45a C45 C44 109.5 . . ?
H45b C45 C44 109.5 . . ?
H45b C45 H45a 109.5 . . ?
H45c C45 C44 109.5 . . ?
H45c C45 H45a 109.5 . . ?
H45c C45 H45b 109.5 . . ?
H46a C46 C44 109.5 . . ?
H46b C46 C44 109.5 . . ?
H46b C46 H46a 109.5 . . ?
H46c C46 C44 109.5 . . ?
H46c C46 H46a 109.5 . . ?
H46c C46 H46b 109.5 . . ?
H47 C47 N3 108.34(10) . . ?
C48 C47 N3 111.87(16) . . ?
C48 C47 H47 108.34(11) . . ?
C51 C47 N3 116.28(16) . . ?
C51 C47 H47 108.34(10) . . ?
C51 C47 C48 103.34(16) . . ?
H48a C48 C47 110.61(11) . . ?
H48b C48 C47 110.61(11) . . ?
H48b C48 H48a 108.7 . . ?
C49 C48 C47 105.67(16) . . ?
C49 C48 H48a 110.61(11) . . ?
C49 C48 H48b 110.61(12) . . ?
H49a C49 C48 110.03(11) . . ?
H49b C49 C48 110.03(12) . . ?
H49b C49 H49a 108.4 . . ?
C50 C49 C48 108.35(16) . . ?
C50 C49 H49a 110.03(10) . . ?
C50 C49 H49b 110.03(11) . . ?
C49 C50 N4 110.01(16) . . ?
C51 C50 N4 113.59(15) . . ?
C51 C50 C49 103.21(16) . . ?
C54 C50 N4 109.91(18) . . ?
C54 C50 C49 108.01(18) . . ?
C54 C50 C51 111.77(18) . . ?
C50 C51 C47 104.10(15) . . ?
C52 C51 C47 106.20(18) . . ?
C52 C51 C50 112.20(17) . . ?
C53 C51 C47 113.85(17) . . ?
C53 C51 C50 113.52(17) . . ?
C53 C51 C52 106.85(18) . . ?
H52a C52 C51 109.5 . . ?
H52b C52 C51 109.5 . . ?
H52b C52 H52a 109.5 . . ?
H52c C52 C51 109.5 . . ?
H52c C52 H52a 109.5 . . ?
H52c C52 H52b 109.5 . . ?
H53a C53 C51 109.5 . . ?
H53b C53 C51 109.5 . . ?
H53b C53 H53a 109.5 . . ?
H53c C53 C51 109.5 . . ?
H53c C53 H53a 109.5 . . ?
H53c C53 H53b 109.5 . . ?
H54a C54 C50 109.5 . . ?
H54b C54 C50 109.5 . . ?
H54b C54 H54a 109.5 . . ?
H54c C54 C50 109.5 . . ?
H54c C54 H54a 109.5 . . ?
H54c C54 H54b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1(3)
2 0(3)

####################################################################### 
# 
# 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_BG002_0m
_database_code_depnum_ccdc_archive 'CCDC 1482176'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C21 H38 B N2, B C24 F20'
_chemical_formula_sum            'C45 H38 B2 F20 N2'
_chemical_formula_weight         1008.43
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           ' P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z

_symmetry_Int_Tables_number      1
_cell_length_a                   12.4169(13)
_cell_length_b                   12.4961(14)
_cell_length_c                   15.9381(17)
_cell_angle_alpha                103.359(5)
_cell_angle_beta                 99.814(5)
_cell_angle_gamma                111.620(5)
_cell_volume                     2145.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9133
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.36
_exptl_crystal_description       block
_exptl_absorpt_coefficient_mu    0.151
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0679 before and 0.0495 after correction.
The Ratio of minimum to maximum transmission is 0.9134.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_density_diffrn    1.5607
_exptl_crystal_F_000             1024.9307
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41777
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.37
_diffrn_ambient_temperature      149.93
_diffrn_measured_fraction_theta_full 0.9172
_diffrn_measured_fraction_theta_max 0.8918
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.813
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                13697
_reflns_number_total             17623
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.3017
_refine_diff_density_min         -0.2798
_refine_diff_density_rms         0.0604
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_d_res_high            0.7690
_refine_ls_d_res_low             14.8749
_refine_ls_goodness_of_fit_ref   1.0425
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    112
_refine_ls_number_parameters     1252
_refine_ls_number_reflns         17623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.0425
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.1100
_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:
 C54(H54), C62(H62), C66(H66), C78(H78), C140(H140), C148(H148)
2.b Secondary CH2 refined with riding coordinates:
 C50(H50a,H50b), C52(H52a,H52b), C55(H55a,H55b), C57(H57a,H57b), C63(H63a,
 H63b), C64(H64a,H64b), C65(H65a,H65b), C67(H67a,H67b), C68(H68a,H68b),
 C69(H69a,H69b), C71(H71a,H71b), C73(H73a,H73b), C76(H76a,H76b), C79(H79a,H79b),
  C141(H14a,H14b), C143(H14c,H14d), C144(H14e,H14f), C145(H14g,H14h), C146(H14i,
 H14j), C147(H14k,H14l)
2.c Idealised Me refined as rotating group:
 C1aa(H1aa,H1ab,H1ac), C51(H51a,H51b,H51c), C53(H53a,H53b,H53c), C56(H56a,H56b,
 H56c), C60(H60a,H60b,H60c), C31(H31a,H31b,H31c), C72(H72a,H72b,H72c), C74(H74a,
 H74b,H74c), C80(H80a,H80b,H80c), C139(H13a,H13b,H13c)
;
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_refinement_flags_posn
N1 N 0.3829(2) 0.9417(2) 0.16091(16) 0.0294(5) Uani 1.000000 .
N2 N 0.3397(2) 0.80256(19) 0.23776(15) 0.0280(5) Uani 1.000000 .
C1aa C 0.3163(3) 1.1102(3) 0.1834(2) 0.0490(8) Uani 1.000000 .
H1aa H 0.3895(6) 1.1630(13) 0.1723(14) 0.0735(12) Uiso 1.000000 GR
H1ab H 0.2521(14) 1.0656(3) 0.1265(8) 0.0735(12) Uiso 1.000000 GR
H1ac H 0.290(2) 1.1599(14) 0.2252(7) 0.0735(12) Uiso 1.000000 GR
C49 C 0.3806(2) 0.8384(2) 0.17297(19) 0.0263(6) Uani 1.000000 .
C50 C 0.4520(3) 0.9910(2) 0.1018(2) 0.0357(7) Uani 1.000000 .
H50a H 0.5106(3) 1.0759(2) 0.1360(2) 0.0428(9) Uiso 1.000000 R
H50b H 0.4990(3) 0.9439(2) 0.0867(2) 0.0428(9) Uiso 1.000000 R
C51 C 0.3799(3) 0.9903(3) 0.0155(2) 0.0469(9) Uani 1.000000 .
H51a H 0.4297(7) 1.001(2) -0.0261(6) 0.0704(13) Uiso 1.000000 GR
H51b H 0.3084(11) 0.9124(8) -0.0117(8) 0.0704(13) Uiso 1.000000 GR
H51c H 0.3546(18) 1.0566(13) 0.0281(3) 0.0704(13) Uiso 1.000000 GR
C52 C 0.3412(3) 0.6922(2) 0.2549(2) 0.0351(7) Uani 1.000000 .
H52a H 0.2625(3) 0.6443(2) 0.2632(2) 0.0421(8) Uiso 1.000000 R
H52b H 0.3515(3) 0.6417(2) 0.2018(2) 0.0421(8) Uiso 1.000000 R
C53 C 0.4418(3) 0.7206(3) 0.3376(2) 0.0495(9) Uani 1.000000 .
H53a H 0.5188(4) 0.7768(16) 0.3334(7) 0.0743(14) Uiso 1.000000 GR
H53b H 0.4245(10) 0.7580(18) 0.3917(3) 0.0743(14) Uiso 1.000000 GR
H53c H 0.4470(13) 0.6452(4) 0.3409(8) 0.0743(14) Uiso 1.000000 GR
C54 C 0.2993(3) 0.8776(2) 0.30013(19) 0.0346(7) Uani 1.000000 .
H54 H 0.2473(3) 0.8293(2) 0.33174(19) 0.0416(8) Uiso 1.000000 R
C55 C 0.4092(3) 0.9886(3) 0.3664(2) 0.0460(8) Uani 1.000000 .
H55a H 0.3894(3) 1.0215(3) 0.4215(2) 0.0552(9) Uiso 1.000000 R
H55b H 0.4775(3) 0.9676(3) 0.3835(2) 0.0552(9) Uiso 1.000000 R
C56 C 0.1782(3) 1.0009(3) 0.3043(2) 0.0443(7) Uani 1.000000 .
H56a H 0.2432(3) 1.0678(12) 0.3543(8) 0.0665(11) Uiso 1.000000 GR
H56b H 0.1342(16) 1.0337(16) 0.2684(4) 0.0665(11) Uiso 1.000000 GR
H56c H 0.1227(15) 0.9454(5) 0.3281(12) 0.0665(11) Uiso 1.000000 GR
C57 C 0.4404(3) 1.0816(3) 0.3143(2) 0.0420(7) Uani 1.000000 .
H57a H 0.4393(3) 1.1584(3) 0.3476(2) 0.0504(9) Uiso 1.000000 R
H57b H 0.5213(3) 1.0996(3) 0.3052(2) 0.0504(9) Uiso 1.000000 R
C58 C 0.3425(3) 1.0204(2) 0.2241(2) 0.0336(7) Uani 1.000000 .
C59 C 0.2327(2) 0.9316(2) 0.24479(19) 0.0331(6) Uani 1.000000 .
C60 C 0.1293(3) 0.8355(3) 0.1618(2) 0.0389(7) Uani 1.000000 .
H60a H 0.0676(8) 0.7799(11) 0.1816(2) 0.0584(11) Uiso 1.000000 GR
H60b H 0.0931(12) 0.8763(3) 0.1282(7) 0.0584(11) Uiso 1.000000 GR
H60c H 0.1615(4) 0.7896(12) 0.1231(7) 0.0584(11) Uiso 1.000000 GR
C62 C 0.5390(3) 0.7375(3) 0.1222(2) 0.0328(7) Uani 1.000000 .
H62 H 0.5906(3) 0.7888(3) 0.1848(2) 0.0394(8) Uiso 1.000000 R
C63 C 0.6050(3) 0.7785(3) 0.0534(2) 0.0432(8) Uani 1.000000 .
H63a H 0.6323(3) 0.8674(3) 0.0675(2) 0.0519(10) Uiso 1.000000 R
H63b H 0.6778(3) 0.7625(3) 0.0608(2) 0.0519(10) Uiso 1.000000 R
C64 C 0.5297(3) 0.7169(3) -0.0442(2) 0.0512(10) Uani 1.000000 .
H64a H 0.5712(3) 0.7630(3) -0.0809(2) 0.0615(12) Uiso 1.000000 R
H64b H 0.5266(3) 0.6344(3) -0.0644(2) 0.0615(12) Uiso 1.000000 R
C65 C 0.4012(3) 0.7054(3) -0.0631(2) 0.0521(10) Uani 1.000000 .
H65a H 0.4028(3) 0.7829(3) -0.0693(2) 0.0625(12) Uiso 1.000000 R
H65b H 0.3535(3) 0.6415(3) -0.1218(2) 0.0625(12) Uiso 1.000000 R
C66 C 0.3341(3) 0.6748(3) 0.0076(2) 0.0424(8) Uani 1.000000 .
H66 H 0.2610(3) 0.6916(3) -0.0024(2) 0.0509(10) Uiso 1.000000 R
C67 C 0.2960(3) 0.5406(3) 0.0054(2) 0.0476(9) Uani 1.000000 .
H67a H 0.2497(3) 0.5256(3) 0.0496(2) 0.0572(10) Uiso 1.000000 R
H67b H 0.2419(3) 0.4861(3) -0.0549(2) 0.0572(10) Uiso 1.000000 R
C68 C 0.5061(3) 0.6009(3) 0.1104(2) 0.0357(7) Uani 1.000000 .
H68a H 0.5793(3) 0.5870(3) 0.1083(2) 0.0428(9) Uiso 1.000000 R
H68b H 0.4837(3) 0.5840(3) 0.1642(2) 0.0428(9) Uiso 1.000000 R
C69 C 0.4033(3) 0.5088(3) 0.0267(2) 0.0428(8) Uani 1.000000 .
H69a H 0.3739(3) 0.4280(3) 0.0354(2) 0.0514(10) Uiso 1.000000 R
H69b H 0.4360(3) 0.5023(3) -0.0258(2) 0.0514(10) Uiso 1.000000 R
B3 B 0.4191(3) 0.7537(3) 0.1035(2) 0.0284(8) Uani 1.000000 .
N3 N 0.0580(2) 0.84071(19) 0.64842(15) 0.0297(5) Uani 1.000000 .
N4 N 0.0081(2) 0.72051(19) 0.73852(15) 0.0293(5) Uani 1.000000 .
C31 C 0.1652(3) 0.8041(2) 0.5334(2) 0.0419(7) Uani 1.000000 .
H31a H 0.1240(8) 0.8398(16) 0.4982(10) 0.0629(11) Uiso 1.000000 GR
H31b H 0.2431(7) 0.8676(13) 0.5732(2) 0.0629(11) Uiso 1.000000 GR
H31c H 0.1785(15) 0.7414(4) 0.4926(10) 0.0629(11) Uiso 1.000000 GR
C70 C 0.0195(2) 0.8214(2) 0.71916(19) 0.0252(6) Uani 1.000000 .
C71 C 0.0654(3) 0.9519(3) 0.6278(2) 0.0373(7) Uani 1.000000 .
H71a H 0.0690(3) 1.0116(3) 0.6825(2) 0.0448(9) Uiso 1.000000 R
H71b H 0.1412(3) 0.9879(3) 0.6115(2) 0.0448(9) Uiso 1.000000 R
C72 C -0.0407(3) 0.9293(3) 0.5516(2) 0.0467(9) Uani 1.000000 .
H72a H -0.0421(11) 0.8739(15) 0.4963(4) 0.0700(13) Uiso 1.000000 GR
H72b H -0.1162(3) 0.8930(18) 0.5669(6) 0.0700(13) Uiso 1.000000 GR
H72c H -0.0322(10) 1.0066(4) 0.5424(10) 0.0700(13) Uiso 1.000000 GR
C73 C -0.0423(3) 0.6899(3) 0.8108(2) 0.0327(7) Uani 1.000000 .
H73a H -0.0759(3) 0.7478(3) 0.8334(2) 0.0393(8) Uiso 1.000000 R
H73b H -0.1098(3) 0.6076(3) 0.7859(2) 0.0393(8) Uiso 1.000000 R
C74 C 0.0481(3) 0.6925(3) 0.8892(2) 0.0459(8) Uani 1.000000 .
H74a H 0.0773(15) 0.6309(14) 0.8686(4) 0.0689(13) Uiso 1.000000 GR
H74b H 0.1163(10) 0.7730(7) 0.9136(10) 0.0689(13) Uiso 1.000000 GR
H74c H 0.0091(6) 0.675(2) 0.9361(6) 0.0689(13) Uiso 1.000000 GR
C75 C 0.0877(2) 0.7476(2) 0.58950(18) 0.0314(6) Uani 1.000000 .
C76 C -0.0300(2) 0.6377(2) 0.53417(18) 0.0300(6) Uani 1.000000 .
H76a H -0.0946(2) 0.6636(2) 0.51693(18) 0.0360(7) Uiso 1.000000 R
H76b H -0.0193(2) 0.5925(2) 0.47882(18) 0.0360(7) Uiso 1.000000 R
C77 C 0.1495(3) 0.6988(2) 0.65509(19) 0.0352(7) Uani 1.000000 .
C78 C 0.0391(3) 0.6297(2) 0.68274(18) 0.0331(7) Uani 1.000000 .
H78 H 0.0542(3) 0.5752(2) 0.71567(18) 0.0397(8) Uiso 1.000000 R
C79 C -0.0627(3) 0.5573(2) 0.59497(18) 0.0373(7) Uani 1.000000 .
H79a H -0.1422(3) 0.5460(2) 0.60491(18) 0.0447(8) Uiso 1.000000 R
H79b H -0.0644(3) 0.4767(2) 0.56830(18) 0.0447(8) Uiso 1.000000 R
C80 C 0.2574(3) 0.7964(3) 0.7330(2) 0.0450(8) Uani 1.000000 .
H80a H 0.2327(5) 0.8557(10) 0.7659(8) 0.0675(12) Uiso 1.000000 GR
H80b H 0.2855(12) 0.7581(4) 0.7737(7) 0.0675(12) Uiso 1.000000 GR
H80c H 0.3229(7) 0.8378(12) 0.7091(2) 0.0675(12) Uiso 1.000000 GR
C139 C 0.1933(3) 0.6080(3) 0.6058(2) 0.0467(8) Uani 1.000000 .
H13a H 0.2179(19) 0.5683(15) 0.6467(5) 0.0700(12) Uiso 1.000000 GR
H13b H 0.1275(6) 0.5465(12) 0.5535(9) 0.0700(12) Uiso 1.000000 GR
H13c H 0.2621(12) 0.6516(4) 0.5857(13) 0.0700(12) Uiso 1.000000 GR
C140 C -0.1216(3) 0.9458(3) 0.7654(2) 0.0356(7) Uani 1.000000 .
H140 H -0.1757(3) 0.8923(3) 0.7040(2) 0.0428(9) Uiso 1.000000 R
C141 C -0.1860(3) 0.9118(3) 0.8374(2) 0.0448(8) Uani 1.000000 .
H14a H -0.2577(3) 0.9296(3) 0.8298(2) 0.0537(10) Uiso 1.000000 R
H14b H -0.2150(3) 0.8231(3) 0.8260(2) 0.0537(10) Uiso 1.000000 R
C143 C -0.1079(3) 0.9775(3) 0.9343(2) 0.0506(9) Uani 1.000000 .
H14c H -0.1028(3) 1.0610(3) 0.9521(2) 0.0607(11) Uiso 1.000000 R
H14d H -0.1487(3) 0.9354(3) 0.9732(2) 0.0607(11) Uiso 1.000000 R
C144 C 0.0199(3) 0.9860(3) 0.9525(2) 0.0452(9) Uani 1.000000 .
H14e H 0.0700(3) 1.0533(3) 1.0090(2) 0.0543(10) Uiso 1.000000 R
H14f H 0.0173(3) 0.9099(3) 0.9625(2) 0.0543(10) Uiso 1.000000 R
C145 C -0.0840(3) 1.0813(3) 0.7719(2) 0.0457(9) Uani 1.000000 .
H14g H -0.0620(3) 1.0924(3) 0.7166(2) 0.0548(11) Uiso 1.000000 R
H14h H -0.1550(3) 1.0994(3) 0.7732(2) 0.0548(11) Uiso 1.000000 R
C146 C 0.0205(3) 1.1737(3) 0.8526(2) 0.0505(10) Uani 1.000000 .
H14i H 0.0515(3) 1.2527(3) 0.8413(2) 0.0605(11) Uiso 1.000000 R
H14j H -0.0103(3) 1.1851(3) 0.9058(2) 0.0605(11) Uiso 1.000000 R
C147 C 0.1243(3) 1.1392(3) 0.8744(2) 0.0468(9) Uani 1.000000 .
H14k H 0.1686(3) 1.1486(3) 0.8285(2) 0.0562(10) Uiso 1.000000 R
H14l H 0.1808(3) 1.1964(3) 0.9333(2) 0.0562(10) Uiso 1.000000 R
C148 C 0.0843(3) 1.0070(3) 0.8778(2) 0.0384(8) Uani 1.000000 .
H148 H 0.1560(3) 0.9880(3) 0.8878(2) 0.0461(9) Uiso 1.000000 R
B4 B -0.0068(3) 0.9219(3) 0.7844(2) 0.0280(8) Uani 1.000000 .
F0aa F -0.27684(15) 0.67992(14) 0.30835(12) 0.0416(5) Uani 1.000000 .
F1aa F -0.33496(13) 0.27730(13) 0.19200(11) 0.0299(4) Uani 1.000000 .
F21 F -0.29853(14) 0.08628(13) 0.07362(11) 0.0330(4) Uani 1.000000 .
F22 F -0.38575(16) 0.04958(17) -0.09881(12) 0.0530(5) Uani 1.000000 .
F23 F -0.28140(18) 0.22094(19) -0.17580(12) 0.0656(7) Uani 1.000000 .
F24 F -0.08668(18) 0.43156(17) -0.07315(12) 0.0601(6) Uani 1.000000 .
F25 F 0.00001(15) 0.47180(14) 0.10185(11) 0.0397(5) Uani 1.000000 .
F26 F -0.20482(14) 0.30603(13) 0.36512(10) 0.0325(4) Uani 1.000000 .
F27 F -0.26850(15) 0.12308(14) 0.42928(11) 0.0395(4) Uani 1.000000 .
F28 F -0.23206(17) -0.07708(15) 0.36107(12) 0.0499(5) Uani 1.000000 .
F29 F -0.13212(16) -0.09067(14) 0.22108(12) 0.0429(5) Uani 1.000000 .
F30 F -0.07183(14) 0.09025(13) 0.15117(10) 0.0318(4) Uani 1.000000 .
F32 F -0.42584(14) 0.43706(14) 0.23425(12) 0.0383(4) Uani 1.000000 .
F34 F -0.03442(15) 0.75540(13) 0.33545(12) 0.0416(5) Uani 1.000000 .
F35 F 0.05943(14) 0.59803(13) 0.29637(11) 0.0355(4) Uani 1.000000 .
F36 F 0.05664(14) 0.42856(14) 0.39181(10) 0.0319(4) Uani 1.000000 .
F37 F 0.28801(15) 0.47376(15) 0.45771(11) 0.0391(4) Uani 1.000000 .
F38 F 0.41858(14) 0.42736(15) 0.34529(12) 0.0407(4) Uani 1.000000 .
F39 F 0.31482(14) 0.34360(14) 0.16315(11) 0.0352(4) Uani 1.000000 .
F40 F 0.08740(14) 0.29336(14) 0.09648(10) 0.0307(4) Uani 1.000000 .
C0aa C -0.1326(2) 0.4272(2) 0.24387(18) 0.0213(6) Uani 1.000000 .
C25 C -0.1422(2) 0.2802(2) 0.09795(18) 0.0220(6) Uani 1.000000 .
C26 C -0.2400(2) 0.1768(2) 0.04212(19) 0.0259(6) Uani 1.000000 .
C27 C -0.2878(3) 0.1547(3) -0.0483(2) 0.0356(8) Uani 1.000000 .
C28 C -0.2365(3) 0.2405(3) -0.0879(2) 0.0396(9) Uani 1.000000 .
C29 C -0.1391(3) 0.3457(3) -0.0360(2) 0.0408(9) Uani 1.000000 .
C30 C -0.0947(3) 0.3649(3) 0.0540(2) 0.0301(7) Uani 1.000000 .
C32 C -0.2550(2) 0.3957(2) 0.22978(18) 0.0229(6) Uani 1.000000 .
C33 C -0.3055(2) 0.4770(2) 0.25068(19) 0.0248(6) Uani 1.000000 .
C34 C -0.2301(3) 0.5991(2) 0.28739(19) 0.0269(7) Uani 1.000000 .
C35 C -0.1094(3) 0.6356(2) 0.30075(19) 0.0265(6) Uani 1.000000 .
C36 C -0.0624(2) 0.5513(2) 0.27939(19) 0.0245(6) Uani 1.000000 .
C37 C -0.1391(2) 0.2070(2) 0.25049(18) 0.0222(6) Uani 1.000000 .
C38 C -0.1877(2) 0.2088(2) 0.32295(18) 0.0243(6) Uani 1.000000 .
C39 C -0.2209(3) 0.1148(3) 0.35950(19) 0.0286(7) Uani 1.000000 .
C40 C -0.2019(3) 0.0142(2) 0.3252(2) 0.0310(7) Uani 1.000000 .
C41 C -0.1519(3) 0.0074(2) 0.2549(2) 0.0305(7) Uani 1.000000 .
C42 C -0.1223(2) 0.1015(2) 0.21960(18) 0.0246(6) Uani 1.000000 .
C43 C 0.0591(2) 0.3616(2) 0.24078(19) 0.0225(6) Uani 1.000000 .
C44 C 0.1183(2) 0.4067(2) 0.33162(19) 0.0241(6) Uani 1.000000 .
C45 C 0.2373(3) 0.4300(2) 0.3681(2) 0.0274(7) Uani 1.000000 .
C46 C 0.3047(2) 0.4077(2) 0.3119(2) 0.0272(7) Uani 1.000000 .
C47 C 0.2502(3) 0.3633(2) 0.2205(2) 0.0279(7) Uani 1.000000 .
C48 C 0.1315(2) 0.3408(2) 0.18755(18) 0.0230(6) Uani 1.000000 .
B2 B -0.0885(3) 0.3191(3) 0.2082(2) 0.0214(7) Uani 1.000000 .
F1 F 0.73891(13) 0.41513(12) 0.69607(10) 0.0281(4) Uani 1.000000 .
F2 F 0.83724(13) 0.26159(14) 0.65576(11) 0.0362(4) Uani 1.000000 .
F3 F 0.69632(15) 0.01767(14) 0.58466(12) 0.0369(4) Uani 1.000000 .
F4 F 0.45309(15) -0.06663(13) 0.55589(12) 0.0419(5) Uani 1.000000 .
F5 F 0.35111(14) 0.08495(13) 0.59080(12) 0.0378(4) Uani 1.000000 .
F6 F 0.39845(16) 0.20664(15) 0.78007(12) 0.0441(5) Uani 1.000000 .
F7 F 0.4872(2) 0.2386(2) 0.95259(14) 0.0778(9) Uani 1.000000 .
F8 F 0.6850(2) 0.4459(2) 1.05741(12) 0.0862(10) Uani 1.000000 .
F9 F 0.78606(18) 0.62239(19) 0.98460(14) 0.0714(7) Uani 1.000000 .
F10 F 0.69627(14) 0.59693(14) 0.81553(12) 0.0398(4) Uani 1.000000 .
F11 F 0.47141(14) 0.59145(13) 0.73909(11) 0.0331(4) Uani 1.000000 .
F12 F 0.53083(16) 0.77628(14) 0.67315(13) 0.0474(5) Uani 1.000000 .
F13 F 0.62909(16) 0.76719(15) 0.53128(13) 0.0501(5) Uani 1.000000 .
F14 F 0.66483(15) 0.56829(15) 0.45873(11) 0.0409(5) Uani 1.000000 .
F15 F 0.60431(14) 0.38309(13) 0.52069(10) 0.0307(4) Uani 1.000000 .
F16 F 0.31393(14) 0.39506(14) 0.78567(10) 0.0335(4) Uani 1.000000 .
F17 F 0.08957(14) 0.35543(16) 0.71566(11) 0.0436(5) Uani 1.000000 .
F18 F -0.01648(15) 0.25384(17) 0.53440(12) 0.0492(5) Uani 1.000000 .
F19 F 0.11354(15) 0.19727(15) 0.42481(11) 0.0405(4) Uani 1.000000 .
F20 F 0.34475(14) 0.24623(13) 0.49272(10) 0.0304(4) Uani 1.000000 .
C1 C 0.5396(2) 0.2601(2) 0.64322(18) 0.0214(6) Uani 1.000000 .
C2 C 0.6635(2) 0.2959(2) 0.65859(17) 0.0203(6) Uani 1.000000 .
C3 C 0.7177(3) 0.2187(2) 0.63891(18) 0.0235(6) Uani 1.000000 .
C4 C 0.6477(3) 0.0964(2) 0.60441(18) 0.0241(6) Uani 1.000000 .
C5 C 0.5245(3) 0.0542(2) 0.5900(2) 0.0279(7) Uani 1.000000 .
C6 C 0.4734(2) 0.1358(2) 0.60892(19) 0.0250(6) Uani 1.000000 .
C7 C 0.5419(3) 0.4003(2) 0.78757(19) 0.0266(7) Uani 1.000000 .
C8 C 0.4939(3) 0.3123(3) 0.8285(2) 0.0364(8) Uani 1.000000 .
C9 C 0.5388(3) 0.3267(3) 0.9176(2) 0.0493(10) Uani 1.000000 .
C10 C 0.6375(4) 0.4301(4) 0.9700(2) 0.0556(12) Uani 1.000000 .
C11 C 0.6896(3) 0.5196(3) 0.9350(2) 0.0466(9) Uani 1.000000 .
C12 C 0.6398(3) 0.5029(3) 0.8446(2) 0.0339(7) Uani 1.000000 .
C13 C 0.5207(2) 0.5817(2) 0.66981(19) 0.0250(6) Uani 1.000000 .
C14 C 0.5507(3) 0.6793(2) 0.6361(2) 0.0314(7) Uani 1.000000 .
C15 C 0.5993(3) 0.6751(3) 0.5654(2) 0.0352(8) Uani 1.000000 .
C16 C 0.6177(3) 0.5743(3) 0.5288(2) 0.0291(7) Uani 1.000000 .
C17 C 0.5857(2) 0.4789(2) 0.56360(18) 0.0236(6) Uani 1.000000 .
C18 C 0.5393(2) 0.4792(2) 0.63691(18) 0.0219(6) Uani 1.000000 .
C19 C 0.3425(2) 0.3192(2) 0.64317(19) 0.0216(6) Uani 1.000000 .
C20 C 0.2697(2) 0.3428(2) 0.69537(19) 0.0252(6) Uani 1.000000 .
C21 C 0.1509(3) 0.3222(3) 0.6610(2) 0.0285(6) Uani 1.000000 .
C22 C 0.0986(3) 0.2730(3) 0.5699(2) 0.0327(7) Uani 1.000000 .
C23 C 0.1651(3) 0.2447(2) 0.51420(19) 0.0279(7) Uani 1.000000 .
C24 C 0.2818(2) 0.2684(2) 0.55105(19) 0.0238(6) Uani 1.000000 .
B1 B 0.4896(3) 0.3641(3) 0.6775(2) 0.0211(7) Uani 1.000000 .


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
N1 C49 1.340(3) . ?
N1 C50 1.468(4) . ?
N1 C58 1.520(3) . ?
N2 C49 1.322(4) . ?
N2 C52 1.472(3) . ?
N2 C54 1.486(3) . ?
C1aa H1aa 0.9800 . ?
C1aa H1ab 0.9800 . ?
C1aa H1ac 0.9800 . ?
C1aa C58 1.523(4) . ?
C49 B3 1.609(4) . ?
C50 H50a 0.9900 . ?
C50 H50b 0.9900 . ?
C50 C51 1.504(4) . ?
C51 H51a 0.9800 . ?
C51 H51b 0.9800 . ?
C51 H51c 0.9800 . ?
C52 H52a 0.9900 . ?
C52 H52b 0.9900 . ?
C52 C53 1.524(5) . ?
C53 H53a 0.9800 . ?
C53 H53b 0.9800 . ?
C53 H53c 0.9800 . ?
C54 H54 1.0000 . ?
C54 C55 1.529(4) . ?
C54 C59 1.534(4) . ?
C55 H55a 0.9900 . ?
C55 H55b 0.9900 . ?
C55 C57 1.554(4) . ?
C56 H56a 0.9800 . ?
C56 H56b 0.9800 . ?
C56 H56c 0.9800 . ?
C56 C59 1.542(4) . ?
C57 H57a 0.9900 . ?
C57 H57b 0.9900 . ?
C57 C58 1.531(4) . ?
C58 C59 1.551(4) . ?
C59 C60 1.546(4) . ?
C60 H60a 0.9800 . ?
C60 H60b 0.9800 . ?
C60 H60c 0.9800 . ?
C62 H62 1.0000 . ?
C62 C63 1.547(4) . ?
C62 C68 1.559(4) . ?
C62 B3 1.563(4) . ?
C63 H63a 0.9900 . ?
C63 H63b 0.9900 . ?
C63 C64 1.519(5) . ?
C64 H64a 0.9900 . ?
C64 H64b 0.9900 . ?
C64 C65 1.518(5) . ?
C65 H65a 0.9900 . ?
C65 H65b 0.9900 . ?
C65 C66 1.547(5) . ?
C66 H66 1.0000 . ?
C66 C67 1.556(4) . ?
C66 B3 1.553(5) . ?
C67 H67a 0.9900 . ?
C67 H67b 0.9900 . ?
C67 C69 1.532(5) . ?
C68 H68a 0.9900 . ?
C68 H68b 0.9900 . ?
C68 C69 1.536(5) . ?
C69 H69a 0.9900 . ?
C69 H69b 0.9900 . ?
N3 C70 1.335(3) . ?
N3 C71 1.474(3) . ?
N3 C75 1.517(3) . ?
N4 C70 1.329(3) . ?
N4 C73 1.463(4) . ?
N4 C78 1.482(3) . ?
C31 H31a 0.9800 . ?
C31 H31b 0.9800 . ?
C31 H31c 0.9800 . ?
C31 C75 1.520(4) . ?
C70 B4 1.607(4) . ?
C71 H71a 0.9900 . ?
C71 H71b 0.9900 . ?
C71 C72 1.522(5) . ?
C72 H72a 0.9800 . ?
C72 H72b 0.9800 . ?
C72 H72c 0.9800 . ?
C73 H73a 0.9900 . ?
C73 H73b 0.9900 . ?
C73 C74 1.515(4) . ?
C74 H74a 0.9800 . ?
C74 H74b 0.9800 . ?
C74 H74c 0.9800 . ?
C75 C76 1.523(4) . ?
C75 C77 1.555(4) . ?
C76 H76a 0.9900 . ?
C76 H76b 0.9900 . ?
C76 C79 1.548(4) . ?
C77 C78 1.526(4) . ?
C77 C80 1.534(4) . ?
C77 C139 1.546(4) . ?
C78 H78 1.0000 . ?
C78 C79 1.531(4) . ?
C79 H79a 0.9900 . ?
C79 H79b 0.9900 . ?
C80 H80a 0.9800 . ?
C80 H80b 0.9800 . ?
C80 H80c 0.9800 . ?
C139 H13a 0.9800 . ?
C139 H13b 0.9800 . ?
C139 H13c 0.9800 . ?
C140 H140 1.0000 . ?
C140 C141 1.556(4) . ?
C140 C145 1.555(4) . ?
C140 B4 1.556(4) . ?
C141 H14a 0.9900 . ?
C141 H14b 0.9900 . ?
C141 C143 1.522(5) . ?
C143 H14c 0.9900 . ?
C143 H14d 0.9900 . ?
C143 C144 1.522(5) . ?
C144 H14e 0.9900 . ?
C144 H14f 0.9900 . ?
C144 C148 1.562(5) . ?
C145 H14g 0.9900 . ?
C145 H14h 0.9900 . ?
C145 C146 1.520(5) . ?
C146 H14i 0.9900 . ?
C146 H14j 0.9900 . ?
C146 C147 1.514(5) . ?
C147 H14k 0.9900 . ?
C147 H14l 0.9900 . ?
C147 C148 1.557(4) . ?
C148 H148 1.0000 . ?
C148 B4 1.560(5) . ?
F0aa C34 1.345(3) . ?
F1aa C32 1.357(3) . ?
F21 C26 1.357(3) . ?
F22 C27 1.362(4) . ?
F23 C28 1.344(3) . ?
F24 C29 1.355(3) . ?
F25 C30 1.347(3) . ?
F26 C38 1.354(3) . ?
F27 C39 1.347(3) . ?
F28 C40 1.351(3) . ?
F29 C41 1.347(3) . ?
F30 C42 1.353(3) . ?
F32 C33 1.345(3) . ?
F34 C35 1.352(3) . ?
F35 C36 1.356(3) . ?
F36 C44 1.365(3) . ?
F37 C45 1.348(3) . ?
F38 C46 1.331(3) . ?
F39 C47 1.354(3) . ?
F40 C48 1.360(3) . ?
C0aa C32 1.385(4) . ?
C0aa C36 1.383(4) . ?
C0aa B2 1.656(4) . ?
C25 C26 1.371(4) . ?
C25 C30 1.408(4) . ?
C25 B2 1.654(4) . ?
C26 C27 1.382(4) . ?
C27 C28 1.378(4) . ?
C28 C29 1.364(5) . ?
C29 C30 1.375(4) . ?
C32 C33 1.385(3) . ?
C33 C34 1.376(4) . ?
C34 C35 1.357(4) . ?
C35 C36 1.387(4) . ?
C37 C38 1.391(4) . ?
C37 C42 1.401(3) . ?
C37 B2 1.656(4) . ?
C38 C39 1.390(4) . ?
C39 C40 1.371(4) . ?
C40 C41 1.371(4) . ?
C41 C42 1.376(4) . ?
C43 C44 1.382(4) . ?
C43 C48 1.388(4) . ?
C43 B2 1.656(4) . ?
C44 C45 1.385(4) . ?
C45 C46 1.375(4) . ?
C46 C47 1.379(4) . ?
C47 C48 1.374(4) . ?
F1 C2 1.350(3) . ?
F2 C3 1.332(3) . ?
F3 C4 1.338(3) . ?
F4 C5 1.354(3) . ?
F5 C6 1.359(3) . ?
F6 C8 1.345(4) . ?
F7 C9 1.348(4) . ?
F8 C10 1.354(4) . ?
F9 C11 1.336(4) . ?
F10 C12 1.357(3) . ?
F11 C13 1.353(3) . ?
F12 C14 1.348(3) . ?
F13 C15 1.343(3) . ?
F14 C16 1.346(3) . ?
F15 C17 1.354(3) . ?
F16 C20 1.353(3) . ?
F17 C21 1.344(3) . ?
F18 C22 1.352(3) . ?
F19 C23 1.345(3) . ?
F20 C24 1.356(3) . ?
C1 C2 1.393(4) . ?
C1 C6 1.379(4) . ?
C1 B1 1.660(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.365(4) . ?
C4 C5 1.378(4) . ?
C5 C6 1.390(4) . ?
C7 C8 1.404(4) . ?
C7 C12 1.373(4) . ?
C7 B1 1.653(4) . ?
C8 C9 1.377(5) . ?
C9 C10 1.362(5) . ?
C10 C11 1.362(5) . ?
C11 C12 1.402(5) . ?
C13 C14 1.397(4) . ?
C13 C18 1.385(4) . ?
C14 C15 1.365(4) . ?
C15 C16 1.377(4) . ?
C16 C17 1.385(4) . ?
C17 C18 1.388(4) . ?
C18 B1 1.668(4) . ?
C19 C20 1.391(4) . ?
C19 C24 1.402(4) . ?
C19 B1 1.647(4) . ?
C20 C21 1.385(4) . ?
C21 C22 1.371(4) . ?
C22 C23 1.384(4) . ?
C23 C24 1.359(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
C50 N1 C49 118.1(2) . . ?
C58 N1 C49 119.8(2) . . ?
C58 N1 C50 120.4(2) . . ?
C52 N2 C49 121.4(2) . . ?
C54 N2 C49 120.8(2) . . ?
C54 N2 C52 117.6(2) . . ?
H1ab C1aa H1aa 109.5 . . ?
H1ac C1aa H1aa 109.5 . . ?
H1ac C1aa H1ab 109.5 . . ?
C58 C1aa H1aa 109.5 . . ?
C58 C1aa H1ab 109.5 . . ?
C58 C1aa H1ac 109.5 . . ?
N2 C49 N1 120.3(2) . . ?
B3 C49 N1 119.2(2) . . ?
B3 C49 N2 120.3(2) . . ?
H50a C50 N1 108.22(15) . . ?
H50b C50 N1 108.22(13) . . ?
H50b C50 H50a 107.4 . . ?
C51 C50 N1 116.3(3) . . ?
C51 C50 H50a 108.22(16) . . ?
C51 C50 H50b 108.22(17) . . ?
H51a C51 C50 109.5 . . ?
H51b C51 C50 109.5 . . ?
H51b C51 H51a 109.5 . . ?
H51c C51 C50 109.5 . . ?
H51c C51 H51a 109.5 . . ?
H51c C51 H51b 109.5 . . ?
H52a C52 N2 109.07(14) . . ?
H52b C52 N2 109.07(14) . . ?
H52b C52 H52a 107.8 . . ?
C53 C52 N2 112.6(2) . . ?
C53 C52 H52a 109.07(17) . . ?
C53 C52 H52b 109.07(18) . . ?
H53a C53 C52 109.5 . . ?
H53b C53 C52 109.5 . . ?
H53b C53 H53a 109.5 . . ?
H53c C53 C52 109.5 . . ?
H53c C53 H53a 109.5 . . ?
H53c C53 H53b 109.5 . . ?
H54 C54 N2 111.79(14) . . ?
C55 C54 N2 109.6(2) . . ?
C55 C54 H54 111.79(16) . . ?
C59 C54 N2 107.4(2) . . ?
C59 C54 H54 111.79(15) . . ?
C59 C54 C55 104.1(2) . . ?
H55a C55 C54 110.90(15) . . ?
H55b C55 C54 110.90(14) . . ?
H55b C55 H55a 108.9 . . ?
C57 C55 C54 104.3(2) . . ?
C57 C55 H55a 110.90(15) . . ?
C57 C55 H55b 110.90(16) . . ?
H56b C56 H56a 109.5 . . ?
H56c C56 H56a 109.5 . . ?
H56c C56 H56b 109.5 . . ?
C59 C56 H56a 109.5 . . ?
C59 C56 H56b 109.5 . . ?
C59 C56 H56c 109.5 . . ?
H57a C57 C55 110.69(15) . . ?
H57b C57 C55 110.69(16) . . ?
H57b C57 H57a 108.8 . . ?
C58 C57 C55 105.3(2) . . ?
C58 C57 H57a 110.69(14) . . ?
C58 C57 H57b 110.69(15) . . ?
C1aa C58 N1 110.9(2) . . ?
C57 C58 N1 107.5(2) . . ?
C57 C58 C1aa 113.4(2) . . ?
C59 C58 N1 106.3(2) . . ?
C59 C58 C1aa 114.2(2) . . ?
C59 C58 C57 104.0(2) . . ?
C56 C59 C54 109.7(2) . . ?
C58 C59 C54 98.4(2) . . ?
C58 C59 C56 111.3(2) . . ?
C60 C59 C54 113.7(2) . . ?
C60 C59 C56 107.9(2) . . ?
C60 C59 C58 115.6(2) . . ?
H60a C60 C59 109.5 . . ?
H60b C60 C59 109.5 . . ?
H60b C60 H60a 109.5 . . ?
H60c C60 C59 109.5 . . ?
H60c C60 H60a 109.5 . . ?
H60c C60 H60b 109.5 . . ?
C63 C62 H62 110.03(17) . . ?
C68 C62 H62 110.03(16) . . ?
C68 C62 C63 111.1(2) . . ?
B3 C62 H62 110.03(17) . . ?
B3 C62 C63 107.3(2) . . ?
B3 C62 C68 108.3(2) . . ?
H63a C63 C62 108.56(15) . . ?
H63b C63 C62 108.56(16) . . ?
H63b C63 H63a 107.5 . . ?
C64 C63 C62 114.8(3) . . ?
C64 C63 H63a 108.56(17) . . ?
C64 C63 H63b 108.56(17) . . ?
H64a C64 C63 108.41(18) . . ?
H64b C64 C63 108.41(17) . . ?
H64b C64 H64a 107.5 . . ?
C65 C64 C63 115.5(3) . . ?
C65 C64 H64a 108.41(17) . . ?
C65 C64 H64b 108.41(17) . . ?
H65a C65 C64 108.15(17) . . ?
H65b C65 C64 108.15(18) . . ?
H65b C65 H65a 107.3 . . ?
C66 C65 C64 116.6(3) . . ?
C66 C65 H65a 108.15(16) . . ?
C66 C65 H65b 108.15(18) . . ?
H66 C66 C65 109.52(17) . . ?
C67 C66 C65 112.9(3) . . ?
C67 C66 H66 109.52(17) . . ?
B3 C66 C65 109.7(3) . . ?
B3 C66 H66 109.52(16) . . ?
B3 C66 C67 105.6(3) . . ?
H67a C67 C66 108.92(17) . . ?
H67b C67 C66 108.92(18) . . ?
H67b C67 H67a 107.7 . . ?
C69 C67 C66 113.3(3) . . ?
C69 C67 H67a 108.92(18) . . ?
C69 C67 H67b 108.92(17) . . ?
H68a C68 C62 108.27(15) . . ?
H68b C68 C62 108.27(16) . . ?
H68b C68 H68a 107.4 . . ?
C69 C68 C62 116.1(2) . . ?
C69 C68 H68a 108.27(16) . . ?
C69 C68 H68b 108.27(17) . . ?
C68 C69 C67 114.4(2) . . ?
H69a C69 C67 108.65(17) . . ?
H69a C69 C68 108.65(15) . . ?
H69b C69 C67 108.65(18) . . ?
H69b C69 C68 108.65(17) . . ?
H69b C69 H69a 107.6 . . ?
C62 B3 C49 126.3(3) . . ?
C66 B3 C49 121.2(3) . . ?
C66 B3 C62 112.5(2) . . ?
C71 N3 C70 117.9(2) . . ?
C75 N3 C70 120.3(2) . . ?
C75 N3 C71 121.7(2) . . ?
C73 N4 C70 122.3(2) . . ?
C78 N4 C70 120.5(2) . . ?
C78 N4 C73 117.0(2) . . ?
H31b C31 H31a 109.5 . . ?
H31c C31 H31a 109.5 . . ?
H31c C31 H31b 109.5 . . ?
C75 C31 H31a 109.5 . . ?
C75 C31 H31b 109.5 . . ?
C75 C31 H31c 109.5 . . ?
N4 C70 N3 119.9(2) . . ?
B4 C70 N3 120.7(2) . . ?
B4 C70 N4 119.3(2) . . ?
H71a C71 N3 108.93(14) . . ?
H71b C71 N3 108.93(14) . . ?
H71b C71 H71a 107.7 . . ?
C72 C71 N3 113.2(2) . . ?
C72 C71 H71a 108.93(16) . . ?
C72 C71 H71b 108.93(16) . . ?
H72a C72 C71 109.5 . . ?
H72b C72 C71 109.5 . . ?
H72b C72 H72a 109.5 . . ?
H72c C72 C71 109.5 . . ?
H72c C72 H72a 109.5 . . ?
H72c C72 H72b 109.5 . . ?
H73a C73 N4 108.73(14) . . ?
H73b C73 N4 108.73(15) . . ?
H73b C73 H73a 107.6 . . ?
C74 C73 N4 114.1(2) . . ?
C74 C73 H73a 108.73(17) . . ?
C74 C73 H73b 108.73(16) . . ?
H74a C74 C73 109.5 . . ?
H74b C74 C73 109.5 . . ?
H74b C74 H74a 109.5 . . ?
H74c C74 C73 109.5 . . ?
H74c C74 H74a 109.5 . . ?
H74c C74 H74b 109.5 . . ?
C31 C75 N3 110.6(2) . . ?
C76 C75 N3 108.5(2) . . ?
C76 C75 C31 113.9(2) . . ?
C77 C75 N3 105.4(2) . . ?
C77 C75 C31 114.0(2) . . ?
C77 C75 C76 103.8(2) . . ?
H76a C76 C75 110.51(14) . . ?
H76b C76 C75 110.51(13) . . ?
H76b C76 H76a 108.7 . . ?
C79 C76 C75 106.1(2) . . ?
C79 C76 H76a 110.51(15) . . ?
C79 C76 H76b 110.51(14) . . ?
C78 C77 C75 97.9(2) . . ?
C80 C77 C75 115.3(2) . . ?
C80 C77 C78 114.9(2) . . ?
C139 C77 C75 112.0(2) . . ?
C139 C77 C78 109.3(2) . . ?
C139 C77 C80 107.3(2) . . ?
C77 C78 N4 107.7(2) . . ?
H78 C78 N4 111.56(14) . . ?
H78 C78 C77 111.56(14) . . ?
C79 C78 N4 108.8(2) . . ?
C79 C78 C77 105.4(2) . . ?
C79 C78 H78 111.56(14) . . ?
C78 C79 C76 103.3(2) . . ?
H79a C79 C76 111.10(15) . . ?
H79a C79 C78 111.10(15) . . ?
H79b C79 C76 111.10(14) . . ?
H79b C79 C78 111.10(14) . . ?
H79b C79 H79a 109.1 . . ?
H80a C80 C77 109.5 . . ?
H80b C80 C77 109.5 . . ?
H80b C80 H80a 109.5 . . ?
H80c C80 C77 109.5 . . ?
H80c C80 H80a 109.5 . . ?
H80c C80 H80b 109.5 . . ?
H13a C139 C77 109.5 . . ?
H13b C139 C77 109.5 . . ?
H13b C139 H13a 109.5 . . ?
H13c C139 C77 109.5 . . ?
H13c C139 H13a 109.5 . . ?
H13c C139 H13b 109.5 . . ?
C141 C140 H140 109.72(17) . . ?
C145 C140 H140 109.72(17) . . ?
C145 C140 C141 112.4(2) . . ?
B4 C140 H140 109.72(16) . . ?
B4 C140 C141 105.7(2) . . ?
B4 C140 C145 109.5(2) . . ?
H14a C141 C140 108.56(16) . . ?
H14b C141 C140 108.56(16) . . ?
H14b C141 H14a 107.5 . . ?
C143 C141 C140 114.8(3) . . ?
C143 C141 H14a 108.56(17) . . ?
C143 C141 H14b 108.56(18) . . ?
H14c C143 C141 108.40(18) . . ?
H14d C143 C141 108.40(18) . . ?
H14d C143 H14c 107.5 . . ?
C144 C143 C141 115.5(3) . . ?
C144 C143 H14c 108.40(17) . . ?
C144 C143 H14d 108.40(18) . . ?
H14e C144 C143 108.17(17) . . ?
H14f C144 C143 108.17(18) . . ?
H14f C144 H14e 107.3 . . ?
C148 C144 C143 116.5(3) . . ?
C148 C144 H14e 108.17(16) . . ?
C148 C144 H14f 108.17(15) . . ?
H14g C145 C140 108.32(17) . . ?
H14h C145 C140 108.32(16) . . ?
H14h C145 H14g 107.4 . . ?
C146 C145 C140 115.8(3) . . ?
C146 C145 H14g 108.3(2) . . ?
C146 C145 H14h 108.32(18) . . ?
H14i C146 C145 108.64(18) . . ?
H14j C146 C145 108.6(2) . . ?
H14j C146 H14i 107.6 . . ?
C147 C146 C145 114.5(3) . . ?
C147 C146 H14i 108.64(18) . . ?
C147 C146 H14j 108.64(19) . . ?
H14k C147 C146 108.79(19) . . ?
H14l C147 C146 108.79(17) . . ?
H14l C147 H14k 107.7 . . ?
C148 C147 C146 113.8(3) . . ?
C148 C147 H14k 108.79(17) . . ?
C148 C147 H14l 108.79(17) . . ?
C147 C148 C144 112.4(2) . . ?
H148 C148 C144 109.77(16) . . ?
H148 C148 C147 109.77(17) . . ?
B4 C148 C144 108.7(3) . . ?
B4 C148 C147 106.4(2) . . ?
B4 C148 H148 109.77(16) . . ?
C140 B4 C70 126.1(3) . . ?
C148 B4 C70 121.6(3) . . ?
C148 B4 C140 112.3(2) . . ?
C36 C0aa C32 113.2(2) . . ?
B2 C0aa C32 118.6(2) . . ?
B2 C0aa C36 127.9(2) . . ?
C30 C25 C26 113.0(2) . . ?
B2 C25 C26 127.4(2) . . ?
B2 C25 C30 119.2(2) . . ?
C25 C26 F21 120.9(2) . . ?
C27 C26 F21 114.4(2) . . ?
C27 C26 C25 124.7(3) . . ?
C26 C27 F22 120.8(3) . . ?
C28 C27 F22 119.4(3) . . ?
C28 C27 C26 119.7(3) . . ?
C27 C28 F23 120.8(3) . . ?
C29 C28 F23 120.7(3) . . ?
C29 C28 C27 118.5(3) . . ?
C28 C29 F24 119.8(3) . . ?
C30 C29 F24 120.1(3) . . ?
C30 C29 C28 120.1(3) . . ?
C25 C30 F25 118.9(2) . . ?
C29 C30 F25 117.1(2) . . ?
C29 C30 C25 124.0(3) . . ?
C0aa C32 F1aa 119.6(2) . . ?
C33 C32 F1aa 115.3(2) . . ?
C33 C32 C0aa 125.0(2) . . ?
C32 C33 F32 120.4(2) . . ?
C34 C33 F32 120.9(2) . . ?
C34 C33 C32 118.7(3) . . ?
C33 C34 F0aa 119.9(3) . . ?
C35 C34 F0aa 121.2(2) . . ?
C35 C34 C33 118.9(2) . . ?
C34 C35 F34 119.6(2) . . ?
C36 C35 F34 119.8(3) . . ?
C36 C35 C34 120.6(2) . . ?
C0aa C36 F35 121.0(2) . . ?
C35 C36 F35 115.5(2) . . ?
C35 C36 C0aa 123.5(3) . . ?
C42 C37 C38 112.8(2) . . ?
B2 C37 C38 126.9(2) . . ?
B2 C37 C42 119.9(2) . . ?
C37 C38 F26 121.6(2) . . ?
C39 C38 F26 114.1(2) . . ?
C39 C38 C37 124.3(2) . . ?
C38 C39 F27 120.6(2) . . ?
C40 C39 F27 120.1(2) . . ?
C40 C39 C38 119.3(3) . . ?
C39 C40 F28 119.9(3) . . ?
C41 C40 F28 120.6(3) . . ?
C41 C40 C39 119.5(2) . . ?
C40 C41 F29 120.0(2) . . ?
C42 C41 F29 120.6(3) . . ?
C42 C41 C40 119.4(2) . . ?
C37 C42 F30 118.8(2) . . ?
C41 C42 F30 116.6(2) . . ?
C41 C42 C37 124.6(3) . . ?
C48 C43 C44 113.0(2) . . ?
B2 C43 C44 119.0(2) . . ?
B2 C43 C48 127.2(2) . . ?
C43 C44 F36 119.1(2) . . ?
C45 C44 F36 116.0(2) . . ?
C45 C44 C43 124.9(2) . . ?
C44 C45 F37 121.1(2) . . ?
C46 C45 F37 119.4(3) . . ?
C46 C45 C44 119.5(3) . . ?
C45 C46 F38 120.7(3) . . ?
C47 C46 F38 121.4(2) . . ?
C47 C46 C45 118.0(3) . . ?
C46 C47 F39 119.6(3) . . ?
C48 C47 F39 120.1(3) . . ?
C48 C47 C46 120.4(2) . . ?
C43 C48 F40 121.2(2) . . ?
C47 C48 F40 114.6(2) . . ?
C47 C48 C43 124.3(3) . . ?
C25 B2 C0aa 101.5(2) . . ?
C37 B2 C0aa 112.2(2) . . ?
C37 B2 C25 114.7(2) . . ?
C43 B2 C0aa 114.9(2) . . ?
C43 B2 C25 112.6(2) . . ?
C43 B2 C37 101.5(2) . . ?
C6 C1 C2 113.2(2) . . ?
B1 C1 C2 119.0(2) . . ?
B1 C1 C6 127.4(2) . . ?
C1 C2 F1 119.1(2) . . ?
C3 C2 F1 115.8(2) . . ?
C3 C2 C1 125.2(2) . . ?
C2 C3 F2 120.8(2) . . ?
C4 C3 F2 120.0(2) . . ?
C4 C3 C2 119.1(3) . . ?
C3 C4 F3 121.3(2) . . ?
C5 C4 F3 119.9(2) . . ?
C5 C4 C3 118.8(2) . . ?
C4 C5 F4 119.9(2) . . ?
C6 C5 F4 120.0(3) . . ?
C6 C5 C4 120.1(2) . . ?
C1 C6 F5 121.0(2) . . ?
C5 C6 F5 115.4(2) . . ?
C5 C6 C1 123.6(3) . . ?
C12 C7 C8 113.6(3) . . ?
B1 C7 C8 118.5(3) . . ?
B1 C7 C12 127.3(2) . . ?
C7 C8 F6 119.8(3) . . ?
C9 C8 F6 116.2(3) . . ?
C9 C8 C7 123.9(3) . . ?
C8 C9 F7 120.6(3) . . ?
C10 C9 F7 120.1(3) . . ?
C10 C9 C8 119.3(3) . . ?
C9 C10 F8 120.7(3) . . ?
C11 C10 F8 119.1(4) . . ?
C11 C10 C9 120.2(3) . . ?
C10 C11 F9 121.8(3) . . ?
C12 C11 F9 119.4(3) . . ?
C12 C11 C10 118.8(3) . . ?
C7 C12 F10 120.9(3) . . ?
C11 C12 F10 115.0(3) . . ?
C11 C12 C7 124.1(3) . . ?
C14 C13 F11 116.3(2) . . ?
C18 C13 F11 119.8(2) . . ?
C18 C13 C14 123.9(3) . . ?
C13 C14 F12 119.9(3) . . ?
C15 C14 F12 120.6(2) . . ?
C15 C14 C13 119.5(2) . . ?
C14 C15 F13 121.1(3) . . ?
C16 C15 F13 119.8(3) . . ?
C16 C15 C14 119.1(2) . . ?
C15 C16 F14 119.9(2) . . ?
C17 C16 F14 120.4(2) . . ?
C17 C16 C15 119.6(3) . . ?
C16 C17 F15 114.6(2) . . ?
C18 C17 F15 121.5(2) . . ?
C18 C17 C16 124.0(2) . . ?
C17 C18 C13 113.8(2) . . ?
B1 C18 C13 119.2(2) . . ?
B1 C18 C17 126.5(2) . . ?
C24 C19 C20 112.8(2) . . ?
B1 C19 C20 126.5(3) . . ?
B1 C19 C24 120.0(2) . . ?
C19 C20 F16 121.0(2) . . ?
C21 C20 F16 114.6(2) . . ?
C21 C20 C19 124.3(3) . . ?
C20 C21 F17 120.5(3) . . ?
C22 C21 F17 120.2(3) . . ?
C22 C21 C20 119.2(3) . . ?
C21 C22 F18 120.5(3) . . ?
C23 C22 F18 120.1(3) . . ?
C23 C22 C21 119.4(3) . . ?
C22 C23 F19 119.2(3) . . ?
C24 C23 F19 121.7(2) . . ?
C24 C23 C22 119.1(3) . . ?
C19 C24 F20 118.4(2) . . ?
C23 C24 F20 116.4(2) . . ?
C23 C24 C19 125.1(2) . . ?
C7 B1 C1 100.0(2) . . ?
C18 B1 C1 112.3(2) . . ?
C18 B1 C7 114.9(2) . . ?
C19 B1 C1 116.0(2) . . ?
C19 B1 C7 113.1(2) . . ?
C19 B1 C18 101.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_JL004_0m
_database_code_depnum_ccdc_archive 'CCDC 1482177'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H42 B Cl N2 O2'
_chemical_formula_sum            'C25 H42 B Cl N2 O2'
_chemical_formula_weight         448.90
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   11.2135(5)
_cell_length_b                   13.8015(6)
_cell_length_c                   16.3539(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2531.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.34
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0677 before and 0.0537 after correction.
The Ratio of minimum to maximum transmission is 0.9379.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.1779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             976.9530
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            43135
_diffrn_reflns_theta_full        27.5584
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.93
_diffrn_ambient_temperature      150.05
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              17
_reflns_limit_k_min              -17
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                5027
_reflns_number_total             5839
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.2769
_refine_diff_density_min         -0.2213
_refine_diff_density_rms         0.0465
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_d_res_high            0.7681
_refine_ls_d_res_low             10.5474
_refine_ls_goodness_of_fit_ref   1.0246
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    64
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5839
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.0246
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+0.5621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0963
_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:
 C1(H1), C2(H2), C5(H5), C10(H10), C12(H12), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C7(H7a,H7b), C8(H8a,H8b), C14(H14a,H14b), C17(H17a,H17b),
 C18(H18a,H18b), C19(H19a,H19b), C21(H21a,H21b), C22(H22a,H22b), C23(H23a,H23b),
  C24(H24a,H24b), C25(H25a,H25b)
2.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c), C4(H4a,H4b,H4c)
;
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_refinement_flags_posn
Cl1 Cl 0.16514(4) 0.35733(3) 0.27772(3) 0.03604(13) Uani 1.000000 .
O1 O 0.30677(12) 0.72421(9) 0.49181(9) 0.0354(3) Uani 1.000000 .
O2 O 0.09792(12) 0.73449(9) 0.34064(9) 0.0342(3) Uani 1.000000 .
N1 N 0.30164(12) 0.57361(9) 0.43365(9) 0.0228(3) Uani 1.000000 .
N2 N 0.17225(13) 0.58008(9) 0.33972(8) 0.0217(3) Uani 1.000000 .
C1 C 0.51796(17) 0.55446(14) 0.47367(13) 0.0337(4) Uani 1.000000 .
H1 H 0.52452(17) 0.49512(14) 0.43887(13) 0.0404(5) Uiso 1.000000 R
C2 C 0.38825(16) 0.56238(12) 0.50144(11) 0.0283(4) Uani 1.000000 .
H2 H 0.36679(16) 0.50415(12) 0.53473(11) 0.0340(5) Uiso 1.000000 R
C3 C 0.24894(14) 0.51764(11) 0.37553(10) 0.0197(3) Uani 1.000000 .
B1 B 0.29002(17) 0.40746(13) 0.34898(12) 0.0225(4) Uani 1.000000 .
C5 C 0.29632(15) 0.34042(12) 0.43097(12) 0.0290(4) Uani 1.000000 .
H5 H 0.36989(15) 0.36050(12) 0.46109(12) 0.0348(5) Uiso 1.000000 R
C6 C 0.3070(3) 0.23092(15) 0.41676(17) 0.0648(9) Uani 1.000000 .
H6a H 0.2338(3) 0.20714(15) 0.38951(17) 0.0777(11) Uiso 1.000000 R
H6b H 0.3753(3) 0.21797(15) 0.37999(17) 0.0777(11) Uiso 1.000000 R
C7 C 0.3250(3) 0.17554(17) 0.4975(2) 0.0777(10) Uani 1.000000 .
H7a H 0.3312(3) 0.10530(17) 0.4860(2) 0.0932(12) Uiso 1.000000 R
H7b H 0.4004(3) 0.19669(17) 0.5234(2) 0.0932(12) Uiso 1.000000 R
C8 C 0.2224(3) 0.19332(16) 0.55572(18) 0.0623(8) Uani 1.000000 .
H8a H 0.1482(3) 0.16597(16) 0.53232(18) 0.0747(9) Uiso 1.000000 R
H8b H 0.2383(3) 0.16002(16) 0.60821(18) 0.0747(9) Uiso 1.000000 R
C9 C -0.1439(2) 0.5170(3) 0.26911(16) 0.0686(8) Uani 1.000000 .
H9a H -0.2114(6) 0.4874(13) 0.2978(4) 0.1028(12) Uiso 1.000000 GR
H9b H -0.1674(12) 0.5809(3) 0.2484(9) 0.1028(12) Uiso 1.000000 GR
H9c H -0.1201(6) 0.4756(12) 0.2233(6) 0.1028(12) Uiso 1.000000 GR
C10 C -0.03988(16) 0.52824(14) 0.32775(11) 0.0308(4) Uani 1.000000 .
H10 H -0.01454(16) 0.46151(14) 0.34406(11) 0.0370(5) Uiso 1.000000 R
C11 C -0.0787(2) 0.57974(16) 0.40466(14) 0.0452(5) Uani 1.000000 .
H11a H -0.1068(13) 0.6450(4) 0.39086(18) 0.0678(8) Uiso 1.000000 GR
H11b H -0.1434(10) 0.5433(6) 0.4307(5) 0.0678(8) Uiso 1.000000 GR
H11c H -0.0110(4) 0.5844(10) 0.4424(4) 0.0678(8) Uiso 1.000000 GR
C12 C 0.06725(15) 0.57589(13) 0.28485(11) 0.0277(4) Uani 1.000000 .
H12 H 0.08739(15) 0.54016(13) 0.23348(11) 0.0333(4) Uiso 1.000000 R
C13 C 0.5976(2) 0.53906(18) 0.54834(15) 0.0514(6) Uani 1.000000 .
H13a H 0.6792(4) 0.5251(12) 0.53036(15) 0.0770(9) Uiso 1.000000 GR
H13b H 0.5974(12) 0.5978(5) 0.5821(6) 0.0770(9) Uiso 1.000000 GR
H13c H 0.5673(9) 0.4844(8) 0.5805(6) 0.0770(9) Uiso 1.000000 GR
C14 C 0.35795(19) 0.65542(14) 0.55016(12) 0.0376(5) Uani 1.000000 .
H14a H 0.43089(19) 0.68273(14) 0.57531(12) 0.0451(6) Uiso 1.000000 R
H14b H 0.29995(19) 0.64078(14) 0.59409(12) 0.0451(6) Uiso 1.000000 R
C15 C 0.25795(15) 0.66760(11) 0.43325(11) 0.0253(4) Uani 1.000000 .
C16 C 0.17681(16) 0.67167(11) 0.37432(11) 0.0251(4) Uani 1.000000 .
C17 C 0.05434(19) 0.68478(14) 0.26751(13) 0.0383(5) Uani 1.000000 .
H17a H -0.03014(19) 0.70156(14) 0.25710(13) 0.0460(6) Uiso 1.000000 R
H17b H 0.10219(19) 0.70341(14) 0.21912(13) 0.0460(6) Uiso 1.000000 R
C18 C 0.19166(17) 0.35506(13) 0.49019(12) 0.0345(4) Uani 1.000000 .
H18a H 0.18361(17) 0.42506(13) 0.50220(12) 0.0414(5) Uiso 1.000000 R
H18b H 0.11723(17) 0.33356(13) 0.46316(12) 0.0414(5) Uiso 1.000000 R
C19 C 0.2058(2) 0.29991(16) 0.57092(15) 0.0525(6) Uani 1.000000 .
H19a H 0.1342(2) 0.31012(16) 0.60522(15) 0.0630(8) Uiso 1.000000 R
H19b H 0.2757(2) 0.32547(16) 0.60100(15) 0.0630(8) Uiso 1.000000 R
C20 C 0.41040(15) 0.41847(12) 0.29258(11) 0.0249(4) Uani 1.000000 .
H20 H 0.47359(15) 0.44413(12) 0.32990(11) 0.0298(4) Uiso 1.000000 R
C21 C 0.46039(19) 0.32431(14) 0.25712(13) 0.0379(5) Uani 1.000000 .
H21a H 0.47443(19) 0.27776(14) 0.30217(13) 0.0455(6) Uiso 1.000000 R
H21b H 0.40069(19) 0.29551(14) 0.21973(13) 0.0455(6) Uiso 1.000000 R
C22 C 0.57707(19) 0.34013(16) 0.21048(14) 0.0446(5) Uani 1.000000 .
H22a H 0.63908(19) 0.36325(16) 0.24890(14) 0.0536(6) Uiso 1.000000 R
H22b H 0.60423(19) 0.27768(16) 0.18725(14) 0.0536(6) Uiso 1.000000 R
C23 C 0.5625(2) 0.41278(18) 0.14253(14) 0.0522(6) Uani 1.000000 .
H23a H 0.6405(2) 0.42391(18) 0.11583(14) 0.0626(7) Uiso 1.000000 R
H23b H 0.5069(2) 0.38667(18) 0.10095(14) 0.0626(7) Uiso 1.000000 R
C24 C 0.5148(2) 0.50757(18) 0.17476(17) 0.0553(7) Uani 1.000000 .
H24a H 0.5753(2) 0.53791(18) 0.21062(17) 0.0664(8) Uiso 1.000000 R
H24b H 0.4997(2) 0.55205(18) 0.12841(17) 0.0664(8) Uiso 1.000000 R
C25 C 0.39914(19) 0.49302(16) 0.22300(15) 0.0445(5) Uani 1.000000 .
H25a H 0.33578(19) 0.47153(16) 0.18494(15) 0.0535(6) Uiso 1.000000 R
H25b H 0.37425(19) 0.55598(16) 0.24646(15) 0.0535(6) Uiso 1.000000 R
C4 C 0.55888(18) 0.64018(17) 0.42199(16) 0.0488(6) Uani 1.000000 .
H4a H 0.5518(14) 0.7000(2) 0.4540(4) 0.0733(8) Uiso 1.000000 GR
H4b H 0.6422(5) 0.6307(6) 0.4058(9) 0.0733(8) Uiso 1.000000 GR
H4c H 0.5089(10) 0.6450(7) 0.3730(5) 0.0733(8) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 B1 1.9488(19) . ?
O1 C14 1.463(2) . ?
O1 C15 1.352(2) . ?
O2 C16 1.356(2) . ?
O2 C17 1.463(3) . ?
N1 C2 1.482(2) . ?
N1 C3 1.360(2) . ?
N1 C15 1.3866(19) . ?
N2 C3 1.351(2) . ?
N2 C12 1.481(2) . ?
N2 C16 1.3859(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.528(3) . ?
C1 C13 1.528(3) . ?
C1 C4 1.525(3) . ?
C2 H2 1.0000 . ?
C2 C14 1.549(3) . ?
C3 B1 1.647(2) . ?
B1 C5 1.631(3) . ?
B1 C20 1.642(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.534(3) . ?
C5 C18 1.535(2) . ?
C6 H6a 0.9900 . ?
C6 H6b 0.9900 . ?
C6 C7 1.539(4) . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C7 C8 1.513(4) . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C19 1.503(3) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C9 C10 1.518(3) . ?
C10 H10 1.0000 . ?
C10 C11 1.509(3) . ?
C10 C12 1.539(3) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C12 H12 1.0000 . ?
C12 C17 1.536(3) . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C15 C16 1.327(3) . ?
C17 H17a 0.9900 . ?
C17 H17b 0.9900 . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C18 C19 1.532(3) . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C20 H20 1.0000 . ?
C20 C21 1.529(2) . ?
C20 C25 1.539(3) . ?
C21 H21a 0.9900 . ?
C21 H21b 0.9900 . ?
C21 C22 1.530(3) . ?
C22 H22a 0.9900 . ?
C22 H22b 0.9900 . ?
C22 C23 1.506(3) . ?
C23 H23a 0.9900 . ?
C23 H23b 0.9900 . ?
C23 C24 1.508(3) . ?
C24 H24a 0.9900 . ?
C24 H24b 0.9900 . ?
C24 C25 1.531(3) . ?
C25 H25a 0.9900 . ?
C25 H25b 0.9900 . ?
C4 H4a 0.9800 . ?
C4 H4b 0.9800 . ?
C4 H4c 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
C15 O1 C14 104.23(13) . . ?
C17 O2 C16 104.49(13) . . ?
C3 N1 C2 138.44(14) . . ?
C15 N1 C2 109.45(13) . . ?
C15 N1 C3 111.99(14) . . ?
C12 N2 C3 138.04(13) . . ?
C16 N2 C3 112.41(13) . . ?
C16 N2 C12 108.19(13) . . ?
C2 C1 H1 107.33(10) . . ?
C13 C1 H1 107.33(12) . . ?
C13 C1 C2 109.21(18) . . ?
C4 C1 H1 107.33(12) . . ?
C4 C1 C2 113.32(16) . . ?
C4 C1 C13 112.02(17) . . ?
C1 C2 N1 114.14(15) . . ?
H2 C2 N1 109.48(9) . . ?
H2 C2 C1 109.48(10) . . ?
C14 C2 N1 98.87(14) . . ?
C14 C2 C1 114.90(15) . . ?
C14 C2 H2 109.48(10) . . ?
N2 C3 N1 102.55(12) . . ?
B1 C3 N1 125.95(14) . . ?
B1 C3 N2 130.74(14) . . ?
C3 B1 Cl1 106.53(11) . . ?
C5 B1 Cl1 108.74(12) . . ?
C5 B1 C3 108.62(14) . . ?
C20 B1 Cl1 106.72(12) . . ?
C20 B1 C3 107.01(12) . . ?
C20 B1 C5 118.60(14) . . ?
H5 C5 B1 106.47(9) . . ?
C6 C5 B1 115.97(17) . . ?
C6 C5 H5 106.47(14) . . ?
C18 C5 B1 114.26(14) . . ?
C18 C5 H5 106.47(10) . . ?
C18 C5 C6 106.56(15) . . ?
H6a C6 C5 109.28(14) . . ?
H6b C6 C5 109.28(11) . . ?
H6b C6 H6a 107.9 . . ?
C7 C6 C5 111.7(2) . . ?
C7 C6 H6a 109.28(17) . . ?
C7 C6 H6b 109.28(13) . . ?
H7a C7 C6 109.42(14) . . ?
H7b C7 C6 109.42(17) . . ?
H7b C7 H7a 108.0 . . ?
C8 C7 C6 111.1(2) . . ?
C8 C7 H7a 109.42(13) . . ?
C8 C7 H7b 109.42(19) . . ?
H8a C8 C7 109.46(19) . . ?
H8b C8 C7 109.46(15) . . ?
H8b C8 H8a 108.1 . . ?
C19 C8 C7 110.9(2) . . ?
C19 C8 H8a 109.46(17) . . ?
C19 C8 H8b 109.46(15) . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
C10 C9 H9a 109.5 . . ?
C10 C9 H9b 109.5 . . ?
C10 C9 H9c 109.5 . . ?
H10 C10 C9 107.06(15) . . ?
C11 C10 C9 110.67(18) . . ?
C11 C10 H10 107.06(12) . . ?
C12 C10 C9 110.83(17) . . ?
C12 C10 H10 107.06(9) . . ?
C12 C10 C11 113.81(16) . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C10 C12 N2 111.17(14) . . ?
H12 C12 N2 110.40(8) . . ?
H12 C12 C10 110.40(9) . . ?
C17 C12 N2 98.54(14) . . ?
C17 C12 C10 115.39(15) . . ?
C17 C12 H12 110.40(10) . . ?
H13a C13 C1 109.5 . . ?
H13b C13 C1 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C1 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C2 C14 O1 106.77(14) . . ?
H14a C14 O1 110.37(9) . . ?
H14a C14 C2 110.37(10) . . ?
H14b C14 O1 110.37(10) . . ?
H14b C14 C2 110.37(10) . . ?
H14b C14 H14a 108.6 . . ?
N1 C15 O1 113.22(15) . . ?
C16 C15 O1 140.17(15) . . ?
C16 C15 N1 106.58(14) . . ?
N2 C16 O2 113.17(15) . . ?
C15 C16 O2 140.34(15) . . ?
C15 C16 N2 106.46(14) . . ?
C12 C17 O2 106.04(14) . . ?
H17a C17 O2 110.53(9) . . ?
H17a C17 C12 110.53(10) . . ?
H17b C17 O2 110.53(10) . . ?
H17b C17 C12 110.53(10) . . ?
H17b C17 H17a 108.7 . . ?
H18a C18 C5 108.87(9) . . ?
H18b C18 C5 108.87(10) . . ?
H18b C18 H18a 107.7 . . ?
C19 C18 C5 113.51(17) . . ?
C19 C18 H18a 108.87(11) . . ?
C19 C18 H18b 108.87(13) . . ?
C18 C19 C8 110.9(2) . . ?
H19a C19 C8 109.46(14) . . ?
H19a C19 C18 109.46(12) . . ?
H19b C19 C8 109.46(17) . . ?
H19b C19 C18 109.46(13) . . ?
H19b C19 H19a 108.1 . . ?
H20 C20 B1 105.82(9) . . ?
C21 C20 B1 115.83(14) . . ?
C21 C20 H20 105.82(11) . . ?
C25 C20 B1 114.19(14) . . ?
C25 C20 H20 105.82(11) . . ?
C25 C20 C21 108.52(16) . . ?
H21a C21 C20 109.12(10) . . ?
H21b C21 C20 109.12(11) . . ?
H21b C21 H21a 107.9 . . ?
C22 C21 C20 112.41(16) . . ?
C22 C21 H21a 109.12(12) . . ?
C22 C21 H21b 109.12(12) . . ?
H22a C22 C21 109.28(12) . . ?
H22b C22 C21 109.28(11) . . ?
H22b C22 H22a 107.9 . . ?
C23 C22 C21 111.72(18) . . ?
C23 C22 H22a 109.28(14) . . ?
C23 C22 H22b 109.28(12) . . ?
H23a C23 C22 109.44(12) . . ?
H23b C23 C22 109.44(14) . . ?
H23b C23 H23a 108.0 . . ?
C24 C23 C22 111.00(19) . . ?
C24 C23 H23a 109.44(12) . . ?
C24 C23 H23b 109.44(15) . . ?
H24a C24 C23 109.33(15) . . ?
H24b C24 C23 109.33(14) . . ?
H24b C24 H24a 108.0 . . ?
C25 C24 C23 111.50(19) . . ?
C25 C24 H24a 109.33(15) . . ?
C25 C24 H24b 109.33(13) . . ?
C24 C25 C20 113.52(17) . . ?
H25a C25 C20 108.86(11) . . ?
H25a C25 C24 108.86(15) . . ?
H25b C25 C20 108.86(11) . . ?
H25b C25 C24 108.86(13) . . ?
H25b C25 H25a 107.7 . . ?
H4a C4 C1 109.5 . . ?
H4b C4 C1 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C1 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1482178'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C23 H39 B N2 O2'
_chemical_formula_sum            'C23 H39 B N2 O2'
_chemical_formula_weight         386.40
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   10.0880(4)
_cell_length_b                   10.1235(5)
_cell_length_c                   21.6378(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2209.78(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9816
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.97
_cell_measurement_theta_min      2.22
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0479 before and 0.0427 after correction.
The Ratio of minimum to maximum transmission is 0.9814.
The λ/2 correction factor is 0.00150
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.1613
_exptl_crystal_description       block
_exptl_crystal_F_000             848.3350
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            90922
_diffrn_reflns_theta_full        27.5412
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.22
_diffrn_ambient_temperature      150.01
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.997
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              28
_reflns_limit_l_min              -27
_reflns_number_gt                4680
_reflns_number_total             5096
_reflns_threshold_expression     I>=2u(I)
_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)'
_refine_diff_density_max         0.2361
_refine_diff_density_min         -0.1730
_refine_diff_density_rms         0.0378
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_d_res_high            0.7685
_refine_ls_d_res_low             9.1695
_refine_ls_goodness_of_fit_ref   1.0868
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     258
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.0868
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²+0.3702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0861
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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:
 C3(H3), C5(H5), C13(H13), C17(H17), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b), C14(H14a,H14b), C15(H15a,H15b), C16(H16a,
 H16b), C18(H18a,H18b), C19(H19a,H19b), C20(H20a,H20b)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C21(H21a,H21b,H21c),
 C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
;
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.044
;
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_refinement_flags_posn
O1 O 0.95957(9) 1.23184(9) 0.89686(5) 0.0290(2) Uani 1.000000 .
O2 O 1.16872(9) 1.00993(10) 0.96363(5) 0.0296(2) Uani 1.000000 .
N1 N 0.86822(10) 1.02734(10) 0.88033(5) 0.0184(2) Uani 1.000000 .
N2 N 1.00444(10) 0.88848(10) 0.91762(4) 0.0170(2) Uani 1.000000 .
C1 C 0.72507(17) 1.19128(16) 0.97855(8) 0.0418(4) Uani 1.000000 .
H1a H 0.6576(2) 1.2037(12) 1.01062(19) 0.0626(6) Uiso 1.000000 GR
H1b H 0.7899(9) 1.1256(6) 0.9924(3) 0.0626(6) Uiso 1.000000 GR
H1c H 0.7701(11) 1.2754(7) 0.97069(17) 0.0626(6) Uiso 1.000000 GR
C2 C 0.65869(13) 1.14302(13) 0.91893(7) 0.0280(3) Uani 1.000000 .
C3 C 0.76035(12) 1.12260(12) 0.86553(6) 0.0225(3) Uani 1.000000 .
H3 H 0.71374(12) 1.09589(12) 0.82670(6) 0.0271(3) Uiso 1.000000 R
C4 C 0.88593(11) 0.89385(12) 0.88644(5) 0.0154(2) Uani 1.000000 .
C5 C 1.09402(11) 0.78938(12) 0.94726(5) 0.0181(2) Uani 1.000000 .
H5 H 1.03962(11) 0.72102(12) 0.96893(5) 0.0217(3) Uiso 1.000000 R
C6 C 1.19475(11) 0.72020(13) 0.90307(5) 0.0198(2) Uani 1.000000 .
C7 C 1.31996(13) 0.68054(15) 0.93903(6) 0.0287(3) Uani 1.000000 .
H7a H 1.29442(13) 0.6357(9) 0.9774(2) 0.0431(4) Uiso 1.000000 GR
H7b H 1.3738(5) 0.6208(8) 0.9137(2) 0.0431(4) Uiso 1.000000 GR
H7c H 1.3715(5) 0.75979(18) 0.9489(4) 0.0431(4) Uiso 1.000000 GR
C8 C 0.55690(17) 1.24487(19) 0.89635(11) 0.0569(6) Uani 1.000000 .
H8a H 0.5219(11) 1.2174(8) 0.8561(3) 0.0853(9) Uiso 1.000000 GR
H8b H 0.4841(8) 1.2509(11) 0.9262(4) 0.0853(9) Uiso 1.000000 GR
H8c H 0.5997(4) 1.3313(4) 0.8923(7) 0.0853(9) Uiso 1.000000 GR
C9 C 0.97271(12) 1.10003(13) 0.90437(6) 0.0225(3) Uani 1.000000 .
C10 C 0.84869(14) 1.24483(14) 0.85376(7) 0.0295(3) Uani 1.000000 .
H10a H 0.79881(14) 1.32730(14) 0.86176(7) 0.0354(4) Uiso 1.000000 R
H10b H 0.88081(14) 1.24593(14) 0.81053(7) 0.0354(4) Uiso 1.000000 R
C11 C 1.05721(12) 1.01284(13) 0.92889(6) 0.0221(3) Uani 1.000000 .
C12 C 1.15620(14) 0.88343(14) 0.99533(6) 0.0268(3) Uani 1.000000 .
H12a H 1.24411(14) 0.85066(14) 1.00868(6) 0.0322(3) Uiso 1.000000 R
H12b H 1.09831(14) 0.89176(14) 1.03207(6) 0.0322(3) Uiso 1.000000 R
C13 C 0.88294(11) 0.73829(12) 0.78678(5) 0.0177(2) Uani 1.000000 .
H13 H 0.98138(11) 0.74552(12) 0.79106(5) 0.0212(3) Uiso 1.000000 R
C14 C 0.83699(12) 0.84619(14) 0.74173(6) 0.0217(3) Uani 1.000000 .
H14a H 0.86479(12) 0.93331(14) 0.75798(6) 0.0260(3) Uiso 1.000000 R
H14b H 0.88191(12) 0.83287(14) 0.70153(6) 0.0260(3) Uiso 1.000000 R
C15 C 0.68669(13) 0.84799(15) 0.73111(6) 0.0274(3) Uani 1.000000 .
H15a H 0.66314(13) 0.93021(15) 0.70891(6) 0.0329(4) Uiso 1.000000 R
H15b H 0.66279(13) 0.77272(15) 0.70412(6) 0.0329(4) Uiso 1.000000 R
C16 C 0.60370(12) 0.83992(14) 0.79047(6) 0.0238(3) Uani 1.000000 .
H16a H 0.59439(12) 0.93036(14) 0.80732(6) 0.0286(3) Uiso 1.000000 R
H16b H 0.51382(12) 0.80887(14) 0.77922(6) 0.0286(3) Uiso 1.000000 R
C17 C 0.65709(11) 0.74980(12) 0.84249(5) 0.0184(2) Uani 1.000000 .
H17 H 0.60871(11) 0.77153(12) 0.88152(5) 0.0220(3) Uiso 1.000000 R
C18 C 0.63276(13) 0.60291(13) 0.82724(6) 0.0229(3) Uani 1.000000 .
H18a H 0.66183(13) 0.54874(13) 0.86283(6) 0.0275(3) Uiso 1.000000 R
H18b H 0.53634(13) 0.58881(13) 0.82186(6) 0.0275(3) Uiso 1.000000 R
C19 C 0.70443(13) 0.55414(14) 0.76909(6) 0.0251(3) Uani 1.000000 .
H19a H 0.70012(13) 0.45647(14) 0.76799(6) 0.0301(3) Uiso 1.000000 R
H19b H 0.65685(13) 0.58776(14) 0.73229(6) 0.0301(3) Uiso 1.000000 R
C20 C 0.85055(13) 0.59676(14) 0.76491(6) 0.0234(3) Uani 1.000000 .
H20a H 0.87933(13) 0.58808(14) 0.72136(6) 0.0281(3) Uiso 1.000000 R
H20b H 0.90414(13) 0.53422(14) 0.78966(6) 0.0281(3) Uiso 1.000000 R
C21 C 1.23718(13) 0.81065(15) 0.84981(6) 0.0280(3) Uani 1.000000 .
H21a H 1.3007(8) 0.7640(4) 0.8234(3) 0.0419(4) Uiso 1.000000 GR
H21b H 1.1592(2) 0.8353(8) 0.8254(3) 0.0419(4) Uiso 1.000000 GR
H21c H 1.2787(9) 0.8905(5) 0.86659(6) 0.0419(4) Uiso 1.000000 GR
C22 C 1.13238(13) 0.59297(13) 0.87857(6) 0.0254(3) Uani 1.000000 .
H22a H 1.0465(5) 0.6132(2) 0.8596(4) 0.0382(4) Uiso 1.000000 GR
H22b H 1.1911(5) 0.5533(5) 0.8476(3) 0.0382(4) Uiso 1.000000 GR
H22c H 1.1195(9) 0.5308(4) 0.91278(10) 0.0382(4) Uiso 1.000000 GR
C23 C 0.58382(14) 1.01567(13) 0.93365(7) 0.0279(3) Uani 1.000000 .
H23a H 0.5245(8) 1.0306(3) 0.9688(3) 0.0418(4) Uiso 1.000000 GR
H23b H 0.5316(8) 0.9888(6) 0.89756(18) 0.0418(4) Uiso 1.000000 GR
H23c H 0.64732(15) 0.9458(3) 0.9440(5) 0.0418(4) Uiso 1.000000 GR
B1 B 0.81685(13) 0.76275(13) 0.85565(6) 0.0155(2) Uani 1.000000 .
H1 H 0.84257(13) 0.68560(13) 0.88190(6) 0.0186(3) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.3507(16) . ?
O1 C10 1.4623(17) . ?
O2 C11 1.3533(15) . ?
O2 C12 1.4581(17) . ?
N1 C3 1.4889(15) . ?
N1 C4 1.3695(15) . ?
N1 C9 1.3869(16) . ?
N2 C4 1.3737(14) . ?
N2 C5 1.4949(15) . ?
N2 C11 1.3885(16) . ?
C1 H1a 0.9800 . ?
C1 H1b 0.9800 . ?
C1 H1c 0.9800 . ?
C1 C2 1.533(2) . ?
C2 C3 1.5589(18) . ?
C2 C8 1.535(2) . ?
C2 C23 1.5277(19) . ?
C3 H3 1.0000 . ?
C3 C10 1.5460(18) . ?
C4 B1 1.6405(17) . ?
C5 H5 1.0000 . ?
C5 C6 1.5612(16) . ?
C5 C12 1.5433(17) . ?
C6 C7 1.5370(17) . ?
C6 C21 1.5329(17) . ?
C6 C22 1.5284(18) . ?
C7 H7a 0.9800 . ?
C7 H7b 0.9800 . ?
C7 H7c 0.9800 . ?
C8 H8a 0.9800 . ?
C8 H8b 0.9800 . ?
C8 H8c 0.9800 . ?
C9 C11 1.3369(19) . ?
C10 H10a 0.9900 . ?
C10 H10b 0.9900 . ?
C12 H12a 0.9900 . ?
C12 H12b 0.9900 . ?
C13 H13 1.0000 . ?
C13 C14 1.5357(17) . ?
C13 C20 1.5439(18) . ?
C13 B1 1.6511(17) . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C14 C15 1.5337(17) . ?
C15 H15a 0.9900 . ?
C15 H15b 0.9900 . ?
C15 C16 1.5353(18) . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C16 C17 1.5458(17) . ?
C17 H17 1.0000 . ?
C17 C18 1.5428(17) . ?
C17 B1 1.6418(17) . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C18 C19 1.5328(17) . ?
C19 H19a 0.9900 . ?
C19 H19b 0.9900 . ?
C19 C20 1.5385(18) . ?
C20 H20a 0.9900 . ?
C20 H20b 0.9900 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
C22 H22a 0.9800 . ?
C22 H22b 0.9800 . ?
C22 H22c 0.9800 . ?
C23 H23a 0.9800 . ?
C23 H23b 0.9800 . ?
C23 H23c 0.9800 . ?
B1 H1 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C9 103.93(10) . . ?
C12 O2 C11 102.03(10) . . ?
C4 N1 C3 139.05(10) . . ?
C9 N1 C3 107.01(10) . . ?
C9 N1 C4 112.84(10) . . ?
C5 N2 C4 139.76(10) . . ?
C11 N2 C4 112.58(10) . . ?
C11 N2 C5 107.54(9) . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
C2 C1 H1a 109.5 . . ?
C2 C1 H1b 109.5 . . ?
C2 C1 H1c 109.5 . . ?
C3 C2 C1 112.24(11) . . ?
C8 C2 C1 110.24(14) . . ?
C8 C2 C3 107.04(12) . . ?
C23 C2 C1 108.03(12) . . ?
C23 C2 C3 111.58(11) . . ?
C23 C2 C8 107.61(12) . . ?
C2 C3 N1 114.03(10) . . ?
H3 C3 N1 110.44(6) . . ?
H3 C3 C2 110.44(7) . . ?
C10 C3 N1 97.62(9) . . ?
C10 C3 C2 113.28(11) . . ?
C10 C3 H3 110.44(7) . . ?
N2 C4 N1 101.54(10) . . ?
B1 C4 N1 134.72(10) . . ?
B1 C4 N2 122.49(10) . . ?
H5 C5 N2 109.51(6) . . ?
C6 C5 N2 115.58(9) . . ?
C6 C5 H5 109.51(7) . . ?
C12 C5 N2 96.94(9) . . ?
C12 C5 H5 109.51(7) . . ?
C12 C5 C6 115.15(10) . . ?
C7 C6 C5 110.00(10) . . ?
C21 C6 C5 111.98(10) . . ?
C21 C6 C7 107.89(10) . . ?
C22 C6 C5 108.82(10) . . ?
C22 C6 C7 107.09(11) . . ?
C22 C6 C21 110.95(10) . . ?
H7a C7 C6 109.5 . . ?
H7b C7 C6 109.5 . . ?
H7b C7 H7a 109.5 . . ?
H7c C7 C6 109.5 . . ?
H7c C7 H7a 109.5 . . ?
H7c C7 H7b 109.5 . . ?
H8a C8 C2 109.5 . . ?
H8b C8 C2 109.5 . . ?
H8b C8 H8a 109.5 . . ?
H8c C8 C2 109.5 . . ?
H8c C8 H8a 109.5 . . ?
H8c C8 H8b 109.5 . . ?
N1 C9 O1 113.86(11) . . ?
C11 C9 O1 139.69(12) . . ?
C11 C9 N1 106.45(11) . . ?
C3 C10 O1 105.30(10) . . ?
H10a C10 O1 110.68(7) . . ?
H10a C10 C3 110.68(7) . . ?
H10b C10 O1 110.68(7) . . ?
H10b C10 C3 110.68(8) . . ?
H10b C10 H10a 108.8 . . ?
N2 C11 O2 113.36(11) . . ?
C9 C11 O2 139.90(12) . . ?
C9 C11 N2 106.53(10) . . ?
C5 C12 O2 105.07(10) . . ?
H12a C12 O2 110.73(6) . . ?
H12a C12 C5 110.73(7) . . ?
H12b C12 O2 110.73(7) . . ?
H12b C12 C5 110.73(7) . . ?
H12b C12 H12a 108.8 . . ?
C14 C13 H13 107.85(6) . . ?
C20 C13 H13 107.85(6) . . ?
C20 C13 C14 113.68(10) . . ?
B1 C13 H13 107.85(6) . . ?
B1 C13 C14 110.14(9) . . ?
B1 C13 C20 109.29(10) . . ?
H14a C14 C13 108.82(7) . . ?
H14b C14 C13 108.82(6) . . ?
H14b C14 H14a 107.7 . . ?
C15 C14 C13 113.70(10) . . ?
C15 C14 H14a 108.82(8) . . ?
C15 C14 H14b 108.82(7) . . ?
H15a C15 C14 108.66(7) . . ?
H15b C15 C14 108.66(8) . . ?
H15b C15 H15a 107.6 . . ?
C16 C15 C14 114.41(11) . . ?
C16 C15 H15a 108.66(7) . . ?
C16 C15 H15b 108.66(7) . . ?
H16a C16 C15 108.10(8) . . ?
H16b C16 C15 108.10(7) . . ?
H16b C16 H16a 107.3 . . ?
C17 C16 C15 116.78(10) . . ?
C17 C16 H16a 108.10(7) . . ?
C17 C16 H16b 108.10(6) . . ?
H17 C17 C16 108.37(6) . . ?
C18 C17 C16 110.96(10) . . ?
C18 C17 H17 108.37(6) . . ?
B1 C17 C16 114.91(10) . . ?
B1 C17 H17 108.37(6) . . ?
B1 C17 C18 105.68(10) . . ?
H18a C18 C17 108.69(7) . . ?
H18b C18 C17 108.69(7) . . ?
H18b C18 H18a 107.6 . . ?
C19 C18 C17 114.27(11) . . ?
C19 C18 H18a 108.69(7) . . ?
C19 C18 H18b 108.69(7) . . ?
H19a C19 C18 108.71(7) . . ?
H19b C19 C18 108.71(7) . . ?
H19b C19 H19a 107.6 . . ?
C20 C19 C18 114.19(10) . . ?
C20 C19 H19a 108.71(7) . . ?
C20 C19 H19b 108.71(7) . . ?
C19 C20 C13 116.42(10) . . ?
H20a C20 C13 108.18(6) . . ?
H20a C20 C19 108.18(7) . . ?
H20b C20 C13 108.18(6) . . ?
H20b C20 C19 108.18(8) . . ?
H20b C20 H20a 107.3 . . ?
H21a C21 C6 109.5 . . ?
H21b C21 C6 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C6 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
H22a C22 C6 109.5 . . ?
H22b C22 C6 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C6 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
H23a C23 C2 109.5 . . ?
H23b C23 C2 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C2 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
C13 B1 C4 108.44(9) . . ?
C17 B1 C4 123.51(10) . . ?
C17 B1 C13 103.17(9) . . ?
H1 B1 C4 106.91(6) . . ?
H1 B1 C13 106.91(6) . . ?
H1 B1 C17 106.91(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_BG004_0m
_database_code_depnum_ccdc_archive 'CCDC 1482179'
_audit_update_record             
;
2016-05-26 deposited with the CCDC.
2016-06-23 downloaded from the CCDC.
;
_audit_creation_date             2016-04-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C23 H21 B F10 N2'
_chemical_formula_sum            'C23 H21 B F10 N2'
_chemical_formula_weight         526.24
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   11.8584(10)
_cell_length_b                   11.9181(10)
_cell_length_c                   16.5677(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2341.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9831
_cell_measurement_theta_max      27.20
_cell_measurement_theta_min      2.46
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0778 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.9406.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.4926
_exptl_crystal_description       triangular
_exptl_crystal_F_000             1072.9402
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39383
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.10
_diffrn_ambient_temperature      150.02
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 0.9974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.996
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                4991
_reflns_number_total             5384
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.2186
_refine_diff_density_min         -0.1583
_refine_diff_density_rms         0.0352
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.0(3)
_refine_ls_d_res_high            0.7696
_refine_ls_d_res_low             9.6749
_refine_ls_goodness_of_fit_ref   1.0421
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5384
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0284
_refine_ls_restrained_S_all      1.0421
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0448P)²+0.3272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0781
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, 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:
 C16(H16), B1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C1aa(H1aa,H1ab), C0aa(H0aa,H0ab)
2.c Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c), C20(H20a,H20b,
 H20c), C21(H21a,H21b,H21c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
F6 F 0.53841(8) 0.12485(7) 0.37899(5) 0.0364(2) Uani 1.000000 .
F10 F 0.61241(7) 0.36704(7) 0.59938(5) 0.03191(18) Uani 1.000000 .
F9 F 0.68979(8) 0.19446(9) 0.68352(5) 0.0450(2) Uani 1.000000 .
F5 F 0.55753(8) 0.60262(7) 0.39497(6) 0.0411(2) Uani 1.000000 .
F1 F 0.36964(7) 0.34801(7) 0.56857(5) 0.0365(2) Uani 1.000000 .
F7 F 0.61602(9) -0.04766(7) 0.46485(7) 0.0509(3) Uani 1.000000 .
F2 F 0.29316(9) 0.51979(10) 0.65564(6) 0.0543(3) Uani 1.000000 .
F4 F 0.47071(10) 0.77278(8) 0.47806(7) 0.0572(3) Uani 1.000000 .
F3 F 0.33940(11) 0.73549(10) 0.61019(8) 0.0651(3) Uani 1.000000 .
F8 F 0.69586(9) -0.01599(9) 0.61767(7) 0.0552(3) Uani 1.000000 .
N2 N 0.55133(9) 0.39584(9) 0.27714(6) 0.0237(2) Uani 1.000000 .
N1 N 0.70715(9) 0.39314(10) 0.35815(6) 0.0240(2) Uani 1.000000 .
C2 C 0.39937(11) 0.45242(12) 0.54473(8) 0.0281(3) Uani 1.000000 .
C10 C 0.65688(12) 0.07185(13) 0.57466(10) 0.0350(3) Uani 1.000000 .
C13 C 0.59435(10) 0.38554(10) 0.35052(7) 0.0204(2) Uani 1.000000 .
C16 C 0.62428(11) 0.41866(12) 0.20633(8) 0.0269(3) Uani 1.000000 .
C7 C 0.57123(10) 0.25596(10) 0.48397(7) 0.0209(2) Uani 1.000000 .
C1 C 0.46975(10) 0.46513(11) 0.47798(8) 0.0230(2) Uani 1.000000 .
C4 C 0.38110(14) 0.64844(14) 0.56784(10) 0.0406(3) Uani 1.000000 .
C14 C 0.78396(11) 0.41043(13) 0.28640(8) 0.0287(3) Uani 1.000000 .
C8 C 0.57603(11) 0.14672(12) 0.45470(8) 0.0261(3) Uani 1.000000 .
C12 C 0.61235(10) 0.26569(11) 0.56202(8) 0.0238(2) Uani 1.000000 .
C9 C 0.61627(12) 0.05565(12) 0.49742(10) 0.0330(3) Uani 1.000000 .
C6 C 0.49089(12) 0.57642(12) 0.45879(9) 0.0291(3) Uani 1.000000 .
C11 C 0.65460(11) 0.17755(13) 0.60729(9) 0.0305(3) Uani 1.000000 .
C15 C 0.73044(12) 0.34677(13) 0.21470(8) 0.0306(3) Uani 1.000000 .
C18 C 0.90319(12) 0.37247(18) 0.30670(11) 0.0468(5) Uani 1.000000 .
B1 B 0.51282(11) 0.35443(12) 0.42833(8) 0.0207(3) Uani 1.000000 .
C3 C 0.35742(13) 0.53985(14) 0.59028(9) 0.0369(3) Uani 1.000000 .
C17 C 0.75611(12) 0.42092(13) 0.43730(8) 0.0305(3) Uani 1.000000 .
C19 C 0.80201(16) 0.35665(16) 0.13708(10) 0.0447(4) Uani 1.000000 .
C5 C 0.44730(14) 0.66725(12) 0.50120(10) 0.0371(3) Uani 1.000000 .
C20 C 0.70725(16) 0.22175(14) 0.22944(10) 0.0436(4) Uani 1.000000 .
C21 C 0.42971(12) 0.39697(14) 0.26039(9) 0.0353(3) Uani 1.000000 .
C1aa C 0.66697(12) 0.54059(12) 0.20931(8) 0.0305(3) Uani 1.000000 .
C0aa C 0.77473(12) 0.53498(13) 0.26222(9) 0.0316(3) Uani 1.000000 .
H16 H 0.58397(11) 0.40267(12) 0.15457(8) 0.0323(3) Uiso 1.000000 R
H18a H 0.9338(5) 0.4200(8) 0.3497(6) 0.0702(7) Uiso 1.000000 GR
H18b H 0.9017(2) 0.2942(4) 0.3249(8) 0.0702(7) Uiso 1.000000 GR
H18c H 0.9509(3) 0.3788(12) 0.2586(3) 0.0702(7) Uiso 1.000000 GR
H1 H 0.44334(11) 0.31984(12) 0.40484(8) 0.0248(3) Uiso 1.000000 R
H17a H 0.69538(12) 0.4350(10) 0.47611(19) 0.0458(5) Uiso 1.000000 GR
H17b H 0.8024(8) 0.3581(4) 0.4562(3) 0.0458(5) Uiso 1.000000 GR
H17c H 0.8032(8) 0.4882(6) 0.43230(17) 0.0458(5) Uiso 1.000000 GR
H19a H 0.7570(4) 0.3328(11) 0.09054(14) 0.0671(6) Uiso 1.000000 GR
H19b H 0.8256(10) 0.4348(3) 0.1297(5) 0.0671(6) Uiso 1.000000 GR
H19c H 0.8688(6) 0.3086(9) 0.1418(4) 0.0671(6) Uiso 1.000000 GR
H20a H 0.6605(10) 0.21313(16) 0.2778(5) 0.0653(6) Uiso 1.000000 GR
H20b H 0.6675(10) 0.1902(3) 0.1828(4) 0.0653(6) Uiso 1.000000 GR
H20c H 0.77886(18) 0.1821(2) 0.2371(8) 0.0653(6) Uiso 1.000000 GR
H21a H 0.4050(2) 0.3214(3) 0.2452(7) 0.0529(5) Uiso 1.000000 GR
H21b H 0.38887(14) 0.4212(10) 0.3088(2) 0.0529(5) Uiso 1.000000 GR
H21c H 0.41407(17) 0.4491(8) 0.2160(5) 0.0529(5) Uiso 1.000000 GR
H1aa H 0.68488(12) 0.56834(12) 0.15447(8) 0.0365(3) Uiso 1.000000 R
H1ab H 0.60987(12) 0.59057(12) 0.23395(8) 0.0365(3) Uiso 1.000000 R
H0aa H 0.76714(12) 0.58331(13) 0.31051(9) 0.0379(4) Uiso 1.000000 R
H0ab H 0.84187(12) 0.55903(13) 0.23119(9) 0.0379(4) Uiso 1.000000 R


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
F6 C8 1.3565(16) . ?
F10 C12 1.3573(15) . ?
F9 C11 1.3453(17) . ?
F5 C6 1.3566(17) . ?
F1 C2 1.3523(16) . ?
F7 C9 1.3443(17) . ?
F2 C3 1.3455(17) . ?
F4 C5 1.3438(18) . ?
F3 C4 1.3465(17) . ?
F8 C10 1.3480(16) . ?
N2 C13 1.3240(16) . ?
N2 C16 1.4828(16) . ?
N2 C21 1.4687(17) . ?
N1 C13 1.3467(16) . ?
N1 C14 1.5117(16) . ?
N1 C17 1.4717(16) . ?
C2 C1 1.3938(18) . ?
C2 C3 1.379(2) . ?
C10 C9 1.381(2) . ?
C10 C11 1.371(2) . ?
C13 B1 1.6535(18) . ?
C16 C15 1.529(2) . ?
C16 C1aa 1.540(2) . ?
C16 H16 1.0000 . ?
C7 C8 1.3905(18) . ?
C7 C12 1.3869(17) . ?
C7 B1 1.6452(18) . ?
C1 C6 1.3867(19) . ?
C1 B1 1.6366(19) . ?
C4 C3 1.376(2) . ?
C4 C5 1.373(2) . ?
C14 C15 1.546(2) . ?
C14 C18 1.5221(19) . ?
C14 C0aa 1.541(2) . ?
C8 C9 1.381(2) . ?
C12 C11 1.3845(19) . ?
C6 C5 1.390(2) . ?
C15 C19 1.545(2) . ?
C15 C20 1.535(2) . ?
C18 H18a 0.9800 . ?
C18 H18b 0.9800 . ?
C18 H18c 0.9800 . ?
B1 H1 1.0000 . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C20 H20a 0.9800 . ?
C20 H20b 0.9800 . ?
C20 H20c 0.9800 . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
C1aa C0aa 1.5511(19) . ?
C1aa H1aa 0.9900 . ?
C1aa H1ab 0.9900 . ?
C0aa H0aa 0.9900 . ?
C0aa H0ab 0.9900 . ?

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
C16 N2 C13 121.24(10) . . ?
C21 N2 C13 123.55(11) . . ?
C21 N2 C16 114.94(10) . . ?
C14 N1 C13 122.26(10) . . ?
C17 N1 C13 119.39(11) . . ?
C17 N1 C14 115.61(10) . . ?
C1 C2 F1 119.20(12) . . ?
C3 C2 F1 116.19(12) . . ?
C3 C2 C1 124.61(13) . . ?
C9 C10 F8 120.05(15) . . ?
C11 C10 F8 120.79(15) . . ?
C11 C10 C9 119.14(13) . . ?
N1 C13 N2 117.56(11) . . ?
B1 C13 N2 120.75(10) . . ?
B1 C13 N1 121.51(10) . . ?
C15 C16 N2 107.81(10) . . ?
C1aa C16 N2 109.85(11) . . ?
C1aa C16 C15 104.79(11) . . ?
H16 C16 N2 111.38(6) . . ?
H16 C16 C15 111.38(7) . . ?
H16 C16 C1aa 111.38(7) . . ?
C12 C7 C8 112.90(11) . . ?
B1 C7 C8 119.32(11) . . ?
B1 C7 C12 127.65(11) . . ?
C6 C1 C2 113.21(12) . . ?
B1 C1 C2 119.88(11) . . ?
B1 C1 C6 126.83(11) . . ?
C3 C4 F3 120.61(15) . . ?
C5 C4 F3 120.21(15) . . ?
C5 C4 C3 119.19(14) . . ?
C15 C14 N1 106.86(10) . . ?
C18 C14 N1 110.21(11) . . ?
C18 C14 C15 113.91(13) . . ?
C0aa C14 N1 107.03(11) . . ?
C0aa C14 C15 104.11(11) . . ?
C0aa C14 C18 114.17(12) . . ?
C7 C8 F6 119.27(12) . . ?
C9 C8 F6 115.89(13) . . ?
C9 C8 C7 124.84(12) . . ?
C7 C12 F10 119.98(11) . . ?
C11 C12 F10 115.34(11) . . ?
C11 C12 C7 124.67(13) . . ?
C10 C9 F7 120.06(13) . . ?
C8 C9 F7 120.88(14) . . ?
C8 C9 C10 119.06(13) . . ?
C1 C6 F5 120.28(12) . . ?
C5 C6 F5 115.55(13) . . ?
C5 C6 C1 124.18(13) . . ?
C10 C11 F9 120.11(13) . . ?
C12 C11 F9 120.47(13) . . ?
C12 C11 C10 119.39(13) . . ?
C14 C15 C16 97.63(11) . . ?
C19 C15 C16 109.51(12) . . ?
C19 C15 C14 112.13(12) . . ?
C20 C15 C16 114.26(13) . . ?
C20 C15 C14 115.32(13) . . ?
C20 C15 C19 107.75(13) . . ?
H18a C18 C14 109.5 . . ?
H18b C18 C14 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 C14 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
C7 B1 C13 110.53(9) . . ?
C1 B1 C13 113.18(10) . . ?
C1 B1 C7 115.14(10) . . ?
H1 B1 C13 105.71(6) . . ?
H1 B1 C7 105.71(6) . . ?
H1 B1 C1 105.71(6) . . ?
C2 C3 F2 120.68(14) . . ?
C4 C3 F2 120.02(14) . . ?
C4 C3 C2 119.29(14) . . ?
H17a C17 N1 109.5 . . ?
H17b C17 N1 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 N1 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H19a C19 C15 109.5 . . ?
H19b C19 C15 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C15 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
C4 C5 F4 120.02(14) . . ?
C6 C5 F4 120.51(14) . . ?
C6 C5 C4 119.46(14) . . ?
H20a C20 C15 109.5 . . ?
H20b C20 C15 109.5 . . ?
H20b C20 H20a 109.5 . . ?
H20c C20 C15 109.5 . . ?
H20c C20 H20a 109.5 . . ?
H20c C20 H20b 109.5 . . ?
H21a C21 N2 109.5 . . ?
H21b C21 N2 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 N2 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C0aa C1aa C16 104.38(11) . . ?
H1aa C1aa C16 110.88(7) . . ?
H1aa C1aa C0aa 110.88(7) . . ?
H1ab C1aa C16 110.88(7) . . ?
H1ab C1aa C0aa 110.88(8) . . ?
H1ab C1aa H1aa 108.9 . . ?
C1aa C0aa C14 104.29(11) . . ?
H0aa C0aa C14 110.90(8) . . ?
H0aa C0aa C1aa 110.90(8) . . ?
H0ab C0aa C14 110.90(7) . . ?
H0ab C0aa C1aa 110.90(7) . . ?
H0ab C0aa H0aa 108.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
