#------------------------------------------------------------------------------
#$Date: 2024-11-09 14:07:10 +0200 (Sat, 09 Nov 2024) $
#$Revision: 295862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/16/7711606.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7711606
loop_
_publ_author_name
'Yoshigoe, Yusuke'
'Hashizume, Keiichiro'
'Saito, Shinichi'
_publ_section_title
;
 Synthesis and stereochemistry of chiral aza-boraspirobifluorenes with
 tetrahedral boron-stereogenic centers
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT03303H
_journal_year                    2022
_chemical_formula_moiety         'C24 H18 B N O'
_chemical_formula_sum            'C24 H18 B N O'
_chemical_formula_weight         347.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-08-23 deposited with the CCDC.	2022-10-27 downloaded from the CCDC.
;
_cell_angle_alpha                109.1900(10)
_cell_angle_beta                 103.359(2)
_cell_angle_gamma                108.8850(10)
_cell_formula_units_Z            4
_cell_length_a                   11.9380(5)
_cell_length_b                   12.7143(5)
_cell_length_c                   14.2807(6)
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      31.03
_cell_measurement_theta_min      2.55
_cell_volume                     1793.52(13)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.780
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1616
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.780
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41838
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.780
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.481
_diffrn_reflns_theta_min         1.875
_diffrn_source                   'sealed tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6960
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1285 before and 0.0525 after correction.
The Ratio of minimum to maximum transmission is 0.9327.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.349
_exptl_crystal_size_min          0.258
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         9289
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0488
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6084
_reflns_number_total             9289
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03303h2.cif
_cod_data_source_block           211006_ysg_hashizume_02_0m_a
_cod_depositor_comments
;

2024-11-09
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C48 H36 B2 N2 O2'
_cod_original_formula_weight         694.41
_cod_original_formula_moiety         '2(C24 H18 B N O)'
_cod_original_formula_units_Z            2
_cod_database_code               7711606
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23), C24(H24), C25(H25),
  C26(H26), C27(H27), C30(H30), C33(H33), C34(H34), C38(H38), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C46(H46), C47(H47), C48(H48)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C32(H32A,H32B,H32C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.04903(12) 1.03494(10) 0.14014(10) 0.0320(3) Uani 1 1 d . . . . .
O2 O 0.49224(12) 0.65495(9) 0.43488(9) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.28627(12) 0.79387(9) 0.32538(9) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.39578(12) 0.56427(9) 0.78221(9) 0.0173(2) Uani 1 1 d . . . . .
C1 C -0.06929(19) 0.93729(16) 0.11625(17) 0.0370(4) Uani 1 1 d . . . . .
H1A H -0.084152 0.864293 0.056645 0.055 Uiso 1 1 calc R U . . .
H1B H -0.137166 0.960774 0.098468 0.055 Uiso 1 1 calc R U . . .
H1C H -0.066544 0.920780 0.177479 0.055 Uiso 1 1 calc R U . . .
C2 C 0.15414(16) 1.01127(12) 0.15715(12) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.15725(15) 0.90870(11) 0.17271(11) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.084431 0.851032 0.171426 0.023 Uiso 1 1 calc R U . . .
C4 C 0.26872(14) 0.89330(11) 0.18997(11) 0.0167(3) Uani 1 1 d . . . . .
C5 C 0.21449(14) 0.68050(11) 0.31569(11) 0.0160(3) Uani 1 1 d . . . . .
C6 C 0.19172(14) 0.66781(11) 0.40384(11) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.142691 0.590455 0.397725 0.022 Uiso 1 1 calc R U . . .
C7 C 0.24277(15) 0.77126(11) 0.49984(12) 0.0197(3) Uani 1 1 d . . . . .
H7 H 0.228805 0.764094 0.559350 0.024 Uiso 1 1 calc R U . . .
C8 C 0.21712(14) 0.64328(11) 0.14334(11) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.17298(13) 0.58818(11) 0.20628(11) 0.0159(3) Uani 1 1 d . . . . .
C10 C 0.09957(14) 0.46105(11) 0.16624(12) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.071806 0.427211 0.209969 0.023 Uiso 1 1 calc R U . . .
C11 C 0.06933(15) 0.38693(11) 0.05993(12) 0.0209(3) Uani 1 1 d . . . . .
H11 H 0.020078 0.302083 0.031259 0.025 Uiso 1 1 calc R U . . .
C12 C 0.11227(15) 0.43872(11) -0.00450(12) 0.0207(3) Uani 1 1 d . . . . .
H12 H 0.091601 0.387805 -0.075850 0.025 Uiso 1 1 calc R U . . .
C13 C 0.18590(14) 0.56594(11) 0.03638(11) 0.0191(3) Uani 1 1 d . . . . .
H13 H 0.214104 0.599113 -0.007569 0.023 Uiso 1 1 calc R U . . .
C14 C 0.31565(15) 0.88718(12) 0.50799(12) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.349947 0.957759 0.572425 0.025 Uiso 1 1 calc R U . . .
C15 C 0.33570(15) 0.89494(11) 0.41901(12) 0.0200(3) Uani 1 1 d . . . . .
H15 H 0.384410 0.971639 0.423764 0.024 Uiso 1 1 calc R U . . .
C16 C 0.45271(14) 0.84256(11) 0.23122(11) 0.0167(3) Uani 1 1 d . . . . .
C17 C 0.54440(15) 0.80150(11) 0.25667(12) 0.0207(3) Uani 1 1 d . . . . .
H17 H 0.522993 0.731452 0.268934 0.025 Uiso 1 1 calc R U . . .
C18 C 0.66897(16) 0.86398(13) 0.26422(12) 0.0241(3) Uani 1 1 d . . . . .
H18 H 0.730109 0.836026 0.281980 0.029 Uiso 1 1 calc R U . . .
C19 C 0.70082(15) 0.96824(12) 0.24496(12) 0.0246(3) Uani 1 1 d . . . . .
H19 H 0.783315 1.009034 0.249075 0.030 Uiso 1 1 calc R U . . .
C20 C 0.61083(15) 1.01238(12) 0.21961(12) 0.0211(3) Uani 1 1 d . . . . .
H20 H 0.632656 1.081926 0.206642 0.025 Uiso 1 1 calc R U . . .
C21 C 0.48725(14) 0.95039(11) 0.21399(11) 0.0183(3) Uani 1 1 d . . . . .
C22 C 0.37891(14) 0.98130(11) 0.19242(11) 0.0174(3) Uani 1 1 d . . . . .
C23 C 0.37545(16) 1.08356(11) 0.17659(12) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.447954 1.141398 0.177643 0.028 Uiso 1 1 calc R U . . .
C24 C 0.26311(17) 1.09794(12) 0.15933(12) 0.0250(3) Uani 1 1 d . . . . .
H24 H 0.260652 1.165877 0.149174 0.030 Uiso 1 1 calc R U . . .
C25 C 0.19379(16) 0.81667(12) 0.88501(13) 0.0238(3) Uani 1 1 d . . . . .
H25 H 0.178880 0.876011 0.932323 0.029 Uiso 1 1 calc R U . . .
C26 C 0.11543(16) 0.75503(12) 0.77671(13) 0.0240(3) Uani 1 1 d . . . . .
H26 H 0.049383 0.774712 0.752157 0.029 Uiso 1 1 calc R U . . .
C27 C 0.13471(14) 0.66395(11) 0.70440(12) 0.0205(3) Uani 1 1 d . . . . .
H27 H 0.081489 0.623665 0.632383 0.025 Uiso 1 1 calc R U . . .
C28 C 0.23281(14) 0.63335(11) 0.73953(11) 0.0173(3) Uani 1 1 d . . . . .
C29 C 0.30857(14) 0.52116(11) 0.57610(11) 0.0174(3) Uani 1 1 d . . . . .
C30 C 0.39919(14) 0.60775(11) 0.56024(11) 0.0185(3) Uani 1 1 d . . . . .
H30 H 0.453250 0.685878 0.616006 0.022 Uiso 1 1 calc R U . . .
C31 C 0.40803(15) 0.57611(12) 0.45991(12) 0.0199(3) Uani 1 1 d . . . . .
C32 C 0.58030(17) 0.77377(12) 0.51886(13) 0.0269(3) Uani 1 1 d . . . . .
H32A H 0.534181 0.818026 0.545574 0.040 Uiso 1 1 calc R U . . .
H32B H 0.635017 0.818919 0.491980 0.040 Uiso 1 1 calc R U . . .
H32C H 0.631106 0.764557 0.575704 0.040 Uiso 1 1 calc R U . . .
C33 C 0.32735(15) 0.45941(13) 0.37566(12) 0.0226(3) Uani 1 1 d . . . . .
H33 H 0.333603 0.440073 0.308930 0.027 Uiso 1 1 calc R U . . .
C34 C 0.23780(15) 0.37203(12) 0.39092(12) 0.0214(3) Uani 1 1 d . . . . .
H34 H 0.184153 0.294028 0.334831 0.026 Uiso 1 1 calc R U . . .
C35 C 0.22898(14) 0.40231(11) 0.49129(11) 0.0192(3) Uani 1 1 d . . . . .
C36 C 0.14715(15) 0.32245(11) 0.52669(12) 0.0195(3) Uani 1 1 d . . . . .
C37 C 0.17062(14) 0.38720(11) 0.63593(12) 0.0192(3) Uani 1 1 d . . . . .
C38 C 0.29365(16) 0.78983(11) 0.92229(12) 0.0214(3) Uani 1 1 d . . . . .
H38 H 0.347355 0.831399 0.994219 0.026 Uiso 1 1 calc R U . . .
C39 C 0.31192(14) 0.69868(11) 0.84924(11) 0.0175(3) Uani 1 1 d . . . . .
C40 C 0.41020(15) 0.65616(11) 0.87353(11) 0.0175(3) Uani 1 1 d . . . . .
C41 C 0.50736(16) 0.69487(12) 0.96969(12) 0.0237(3) Uani 1 1 d . . . . .
H41 H 0.517009 0.757092 1.032182 0.028 Uiso 1 1 calc R U . . .
C42 C 0.58955(17) 0.63944(13) 0.97107(13) 0.0272(3) Uani 1 1 d . . . . .
H42 H 0.654932 0.663922 1.034921 0.033 Uiso 1 1 calc R U . . .
C43 C 0.57442(16) 0.54673(13) 0.87664(13) 0.0257(3) Uani 1 1 d . . . . .
H43 H 0.629866 0.509498 0.876651 0.031 Uiso 1 1 calc R U . . .
C44 C 0.47601(15) 0.51125(12) 0.78339(12) 0.0210(3) Uani 1 1 d . . . . .
H44 H 0.465121 0.449340 0.720113 0.025 Uiso 1 1 calc R U . . .
C45 C 0.10580(16) 0.32523(13) 0.68459(13) 0.0248(3) Uani 1 1 d . . . . .
H45 H 0.120669 0.366875 0.756547 0.030 Uiso 1 1 calc R U . . .
C46 C 0.01792(16) 0.20025(13) 0.62639(14) 0.0284(3) Uani 1 1 d . . . . .
H46 H -0.024656 0.159015 0.659799 0.034 Uiso 1 1 calc R U . . .
C47 C -0.00524(15) 0.13844(12) 0.51898(14) 0.0280(3) Uani 1 1 d . . . . .
H47 H -0.064596 0.055921 0.480251 0.034 Uiso 1 1 calc R U . . .
C48 C 0.05912(16) 0.19823(12) 0.46841(13) 0.0251(3) Uani 1 1 d . . . . .
H48 H 0.043725 0.155926 0.396428 0.030 Uiso 1 1 calc R U . . .
B1 B 0.30296(16) 0.78953(12) 0.21594(13) 0.0170(3) Uani 1 1 d . . . . .
B2 B 0.27477(17) 0.52911(13) 0.68079(13) 0.0178(3) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 1.00 0.0520
0.00 0.00 -1.00 0.1110
0.00 0.00 1.00 0.1340
1.00 0.00 1.00 0.1020
1.00 -1.00 1.00 0.1940
1.00 1.00 1.00 0.1190
0.00 1.00 0.00 0.1560
0.00 -1.00 0.00 0.2370
-1.00 -1.00 0.00 0.1990
1.00 0.00 0.00 0.1720
-1.00 0.00 0.00 0.1300
-1.00 1.00 0.00 0.0210
1.00 -1.00 0.00 0.1720
-1.00 -1.00 1.00 0.2510
-1.00 0.00 1.00 0.2010
0.00 -1.00 1.00 0.2680
-1.00 -1.00 -1.00 0.1900
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
C2 O1 C1 116.62(10) . . ?
C31 O2 C32 117.39(11) . . ?
C5 N1 B1 112.74(10) . . ?
C15 N1 C5 120.86(11) . . ?
C15 N1 B1 126.40(10) . . ?
C40 N2 B2 112.81(11) . . ?
C44 N2 C40 120.72(13) . . ?
C44 N2 B2 126.46(12) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.40(14) . . ?
O1 C2 C24 115.49(11) . . ?
C24 C2 C3 120.11(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.04(13) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C22 119.73(11) . . ?
C3 C4 B1 131.10(12) . . ?
C22 C4 B1 109.09(12) . . ?
N1 C5 C6 120.04(12) . . ?
N1 C5 C9 109.38(11) . . ?
C6 C5 C9 130.58(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.09(11) . . ?
C7 C6 H6 120.5 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C14 120.00(12) . . ?
C14 C7 H7 120.0 . . ?
C9 C8 B1 109.62(11) . . ?
C13 C8 C9 117.64(10) . . ?
C13 C8 B1 132.67(11) . . ?
C8 C9 C5 111.02(10) . . ?
C10 C9 C5 126.11(11) . . ?
C10 C9 C8 122.87(12) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 C9 118.22(12) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.30(11) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.03(13) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 119.93(12) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C7 C14 H14 120.6 . . ?
C15 C14 C7 118.78(13) . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 121.23(11) . . ?
N1 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C21 118.89(13) . . ?
C17 C16 B1 131.81(11) . . ?
C21 C16 B1 109.29(12) . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C18 120.87(12) . . ?
C18 C17 H17 119.6 . . ?
C17 C18 H18 120.2 . . ?
C19 C18 C17 119.60(14) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.5 . . ?
C18 C19 C20 120.96(14) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.5 . . ?
C19 C20 C21 118.94(12) . . ?
C21 C20 H20 120.5 . . ?
C16 C21 C22 110.53(12) . . ?
C20 C21 C16 120.71(13) . . ?
C20 C21 C22 128.76(11) . . ?
C4 C22 C21 111.57(10) . . ?
C23 C22 C4 120.12(14) . . ?
C23 C22 C21 128.31(13) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.60(13) . . ?
C24 C23 H23 120.2 . . ?
C2 C24 H24 119.8 . . ?
C23 C24 C2 120.41(11) . . ?
C23 C24 H24 119.8 . . ?
C26 C25 H25 119.9 . . ?
C38 C25 H25 119.9 . . ?
C38 C25 C26 120.15(13) . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 120.92(14) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.38(14) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 C39 117.46(12) . . ?
C27 C28 B2 132.98(13) . . ?
C39 C28 B2 109.46(12) . . ?
C30 C29 C35 119.62(12) . . ?
C30 C29 B2 131.22(12) . . ?
C35 C29 B2 109.16(11) . . ?
C29 C30 H30 120.3 . . ?
C29 C30 C31 119.33(13) . . ?
C31 C30 H30 120.3 . . ?
O2 C31 C30 124.19(13) . . ?
O2 C31 C33 114.93(12) . . ?
C33 C31 C30 120.86(13) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33 119.9 . . ?
C34 C33 C31 120.28(13) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.3 . . ?
C33 C34 C35 119.33(13) . . ?
C35 C34 H34 120.3 . . ?
C29 C35 C36 111.03(12) . . ?
C34 C35 C29 120.56(13) . . ?
C34 C35 C36 128.36(12) . . ?
C37 C36 C35 110.71(11) . . ?
C48 C36 C35 128.70(14) . . ?
C48 C36 C37 120.56(13) . . ?
C36 C37 B2 109.11(11) . . ?
C45 C37 C36 118.94(13) . . ?
C45 C37 B2 131.94(13) . . ?
C25 C38 H38 120.8 . . ?
C25 C38 C39 118.36(14) . . ?
C39 C38 H38 120.8 . . ?
C28 C39 C40 110.91(11) . . ?
C38 C39 C28 122.71(14) . . ?
C38 C39 C40 126.37(13) . . ?
N2 C40 C39 109.33(12) . . ?
N2 C40 C41 120.40(13) . . ?
C41 C40 C39 130.27(12) . . ?
C40 C41 H41 120.6 . . ?
C42 C41 C40 118.87(14) . . ?
C42 C41 H41 120.6 . . ?
C41 C42 H42 120.0 . . ?
C41 C42 C43 119.96(15) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 120.6 . . ?
C44 C43 C42 118.87(14) . . ?
C44 C43 H43 120.6 . . ?
N2 C44 C43 121.16(13) . . ?
N2 C44 H44 119.4 . . ?
C43 C44 H44 119.4 . . ?
C37 C45 H45 119.7 . . ?
C37 C45 C46 120.60(15) . . ?
C46 C45 H45 119.7 . . ?
C45 C46 H46 120.1 . . ?
C47 C46 C45 119.77(14) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 119.6 . . ?
C46 C47 C48 120.78(13) . . ?
C48 C47 H47 119.6 . . ?
C36 C48 H48 120.3 . . ?
C47 C48 C36 119.34(15) . . ?
C47 C48 H48 120.3 . . ?
N1 B1 C4 109.53(10) . . ?
N1 B1 C8 97.20(9) . . ?
N1 B1 C16 111.39(12) . . ?
C8 B1 C4 122.87(12) . . ?
C8 B1 C16 116.56(11) . . ?
C16 B1 C4 99.47(10) . . ?
N2 B2 C28 97.32(11) . . ?
N2 B2 C29 112.84(12) . . ?
N2 B2 C37 110.80(10) . . ?
C28 B2 C29 121.20(11) . . ?
C28 B2 C37 115.37(12) . . ?
C29 B2 C37 99.76(11) . . ?
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 C1 1.420(2) . ?
O1 C2 1.3696(19) . ?
O2 C31 1.3757(16) . ?
O2 C32 1.4227(19) . ?
N1 C5 1.3586(14) . ?
N1 C15 1.3426(18) . ?
N1 B1 1.6061(19) . ?
N2 C40 1.3636(17) . ?
N2 C44 1.3380(17) . ?
N2 B2 1.604(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.4034(17) . ?
C2 C24 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 C22 1.4084(18) . ?
C4 B1 1.6267(18) . ?
C5 C6 1.3956(18) . ?
C5 C9 1.4575(19) . ?
C6 H6 0.9300 . ?
C6 C7 1.3750(19) . ?
C7 H7 0.9300 . ?
C7 C14 1.3974(17) . ?
C8 C9 1.4036(17) . ?
C8 C13 1.3969(19) . ?
C8 B1 1.6096(18) . ?
C9 C10 1.3970(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.3932(19) . ?
C12 H12 0.9300 . ?
C12 C13 1.3969(17) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.3745(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(2) . ?
C16 C21 1.4188(16) . ?
C16 B1 1.625(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.3926(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.398(2) . ?
C21 C22 1.465(2) . ?
C22 C23 1.4025(16) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(2) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.393(2) . ?
C25 C38 1.382(2) . ?
C26 H26 0.9300 . ?
C26 C27 1.399(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(2) . ?
C28 C39 1.410(2) . ?
C28 B2 1.6137(19) . ?
C29 C30 1.3927(18) . ?
C29 C35 1.4102(19) . ?
C29 B2 1.617(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.3944(19) . ?
C31 C33 1.394(2) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 0.9300 . ?
C33 C34 1.387(2) . ?
C34 H34 0.9300 . ?
C34 C35 1.395(2) . ?
C35 C36 1.4713(19) . ?
C36 C37 1.412(2) . ?
C36 C48 1.3960(19) . ?
C37 C45 1.3843(19) . ?
C37 B2 1.622(2) . ?
C38 H38 0.9300 . ?
C38 C39 1.3975(18) . ?
C39 C40 1.461(2) . ?
C40 C41 1.387(2) . ?
C41 H41 0.9300 . ?
C41 C42 1.381(2) . ?
C42 H42 0.9300 . ?
C42 C43 1.395(2) . ?
C43 H43 0.9300 . ?
C43 C44 1.377(2) . ?
C44 H44 0.9300 . ?
C45 H45 0.9300 . ?
C45 C46 1.402(2) . ?
C46 H46 0.9300 . ?
C46 C47 1.385(2) . ?
C47 H47 0.9300 . ?
C47 C48 1.389(2) . ?
C48 H48 0.9300 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.62(13) . . . . ?
O1 C2 C24 C23 179.65(14) . . . . ?
O2 C31 C33 C34 -179.65(13) . . . . ?
N1 C5 C6 C7 0.0(2) . . . . ?
N1 C5 C9 C8 -0.99(16) . . . . ?
N1 C5 C9 C10 178.76(14) . . . . ?
N2 C40 C41 C42 0.5(2) . . . . ?
C1 O1 C2 C3 -12.7(2) . . . . ?
C1 O1 C2 C24 167.81(15) . . . . ?
C2 C3 C4 C22 0.4(2) . . . . ?
C2 C3 C4 B1 176.57(14) . . . . ?
C3 C2 C24 C23 0.2(2) . . . . ?
C3 C4 C22 C21 178.70(12) . . . . ?
C3 C4 C22 C23 -0.5(2) . . . . ?
C3 C4 B1 N1 -60.04(19) . . . . ?
C3 C4 B1 C8 52.8(2) . . . . ?
C3 C4 B1 C16 -176.88(14) . . . . ?
C4 C22 C23 C24 0.5(2) . . . . ?
C5 N1 C15 C14 0.1(2) . . . . ?
C5 N1 B1 C4 130.27(12) . . . . ?
C5 N1 B1 C8 1.56(15) . . . . ?
C5 N1 B1 C16 -120.68(12) . . . . ?
C5 C6 C7 C14 0.4(2) . . . . ?
C5 C9 C10 C11 -179.81(14) . . . . ?
C6 C5 C9 C8 179.11(15) . . . . ?
C6 C5 C9 C10 -1.1(3) . . . . ?
C6 C7 C14 C15 -0.6(2) . . . . ?
C7 C14 C15 N1 0.3(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C5 C6 C7 179.93(14) . . . . ?
C9 C8 C13 C12 0.5(2) . . . . ?
C9 C8 B1 N1 -2.09(14) . . . . ?
C9 C8 B1 C4 -120.96(14) . . . . ?
C9 C8 B1 C16 116.22(13) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C11 C12 C13 C8 -0.2(2) . . . . ?
C13 C8 C9 C5 179.36(13) . . . . ?
C13 C8 C9 C10 -0.4(2) . . . . ?
C13 C8 B1 N1 -178.85(15) . . . . ?
C13 C8 B1 C4 62.3(2) . . . . ?
C13 C8 B1 C16 -60.5(2) . . . . ?
C15 N1 C5 C6 -0.3(2) . . . . ?
C15 N1 C5 C9 179.79(12) . . . . ?
C15 N1 B1 C4 -50.07(19) . . . . ?
C15 N1 B1 C8 -178.77(13) . . . . ?
C15 N1 B1 C16 58.98(17) . . . . ?
C16 C17 C18 C19 -0.6(2) . . . . ?
C16 C21 C22 C4 -2.56(16) . . . . ?
C16 C21 C22 C23 176.57(14) . . . . ?
C17 C16 C21 C20 1.8(2) . . . . ?
C17 C16 C21 C22 -177.70(12) . . . . ?
C17 C16 B1 N1 63.36(18) . . . . ?
C17 C16 B1 C4 178.78(14) . . . . ?
C17 C16 B1 C8 -46.9(2) . . . . ?
C17 C18 C19 C20 0.8(2) . . . . ?
C18 C19 C20 C21 0.2(2) . . . . ?
C19 C20 C21 C16 -1.5(2) . . . . ?
C19 C20 C21 C22 177.87(13) . . . . ?
C20 C21 C22 C4 178.02(14) . . . . ?
C20 C21 C22 C23 -2.9(2) . . . . ?
C21 C16 C17 C18 -0.7(2) . . . . ?
C21 C16 B1 N1 -116.56(11) . . . . ?
C21 C16 B1 C4 -1.14(14) . . . . ?
C21 C16 B1 C8 133.18(12) . . . . ?
C21 C22 C23 C24 -178.57(14) . . . . ?
C22 C4 B1 N1 116.49(12) . . . . ?
C22 C4 B1 C8 -130.71(13) . . . . ?
C22 C4 B1 C16 -0.36(14) . . . . ?
C22 C23 C24 C2 -0.3(2) . . . . ?
C24 C2 C3 C4 -0.2(2) . . . . ?
C25 C26 C27 C28 -0.04(19) . . . . ?
C25 C38 C39 C28 -0.02(18) . . . . ?
C25 C38 C39 C40 -178.89(12) . . . . ?
C26 C25 C38 C39 -1.05(19) . . . . ?
C26 C27 C28 C39 -0.99(17) . . . . ?
C26 C27 C28 B2 175.17(13) . . . . ?
C27 C28 C39 C38 1.04(18) . . . . ?
C27 C28 C39 C40 -179.94(11) . . . . ?
C27 C28 B2 N2 179.68(13) . . . . ?
C27 C28 B2 C29 57.3(2) . . . . ?
C27 C28 B2 C37 -63.12(18) . . . . ?
C28 C39 C40 N2 -0.45(14) . . . . ?
C28 C39 C40 C41 179.52(13) . . . . ?
C29 C30 C31 O2 178.78(13) . . . . ?
C29 C30 C31 C33 0.1(2) . . . . ?
C29 C35 C36 C37 0.25(17) . . . . ?
C29 C35 C36 C48 -177.61(14) . . . . ?
C30 C29 C35 C34 -1.8(2) . . . . ?
C30 C29 C35 C36 175.75(12) . . . . ?
C30 C29 B2 N2 -56.72(18) . . . . ?
C30 C29 B2 C28 57.9(2) . . . . ?
C30 C29 B2 C37 -174.32(14) . . . . ?
C30 C31 C33 C34 -0.9(2) . . . . ?
C31 C33 C34 C35 0.3(2) . . . . ?
C32 O2 C31 C30 3.6(2) . . . . ?
C32 O2 C31 C33 -177.65(13) . . . . ?
C33 C34 C35 C29 1.1(2) . . . . ?
C33 C34 C35 C36 -176.04(14) . . . . ?
C34 C35 C36 C37 177.62(14) . . . . ?
C34 C35 C36 C48 -0.2(2) . . . . ?
C35 C29 C30 C31 1.2(2) . . . . ?
C35 C29 B2 N2 122.24(12) . . . . ?
C35 C29 B2 C28 -123.13(14) . . . . ?
C35 C29 B2 C37 4.63(15) . . . . ?
C35 C36 C37 C45 -177.47(13) . . . . ?
C35 C36 C37 B2 2.94(16) . . . . ?
C35 C36 C48 C47 177.50(14) . . . . ?
C36 C37 C45 C46 -0.2(2) . . . . ?
C36 C37 B2 N2 -123.61(12) . . . . ?
C36 C37 B2 C28 127.07(13) . . . . ?
C36 C37 B2 C29 -4.49(15) . . . . ?
C37 C36 C48 C47 -0.2(2) . . . . ?
C37 C45 C46 C47 -0.6(2) . . . . ?
C38 C25 C26 C27 1.10(19) . . . . ?
C38 C39 C40 N2 178.53(12) . . . . ?
C38 C39 C40 C41 -1.5(2) . . . . ?
C39 C28 B2 N2 -3.93(12) . . . . ?
C39 C28 B2 C29 -126.30(14) . . . . ?
C39 C28 B2 C37 113.27(14) . . . . ?
C39 C40 C41 C42 -179.48(13) . . . . ?
C40 N2 C44 C43 0.68(19) . . . . ?
C40 N2 B2 C28 3.82(12) . . . . ?
C40 N2 B2 C29 132.20(11) . . . . ?
C40 N2 B2 C37 -116.90(12) . . . . ?
C40 C41 C42 C43 0.4(2) . . . . ?
C41 C42 C43 C44 -0.7(2) . . . . ?
C42 C43 C44 N2 0.2(2) . . . . ?
C44 N2 C40 C39 178.96(11) . . . . ?
C44 N2 C40 C41 -1.01(18) . . . . ?
C44 N2 B2 C28 -177.64(11) . . . . ?
C44 N2 B2 C29 -49.26(16) . . . . ?
C44 N2 B2 C37 61.63(17) . . . . ?
C45 C37 B2 N2 56.9(2) . . . . ?
C45 C37 B2 C28 -52.4(2) . . . . ?
C45 C37 B2 C29 176.00(15) . . . . ?
C45 C46 C47 C48 1.0(2) . . . . ?
C46 C47 C48 C36 -0.6(2) . . . . ?
C48 C36 C37 C45 0.6(2) . . . . ?
C48 C36 C37 B2 -178.99(13) . . . . ?
B1 N1 C5 C6 179.39(12) . . . . ?
B1 N1 C5 C9 -0.52(16) . . . . ?
B1 N1 C15 C14 -179.51(14) . . . . ?
B1 C4 C22 C21 1.72(15) . . . . ?
B1 C4 C22 C23 -177.49(12) . . . . ?
B1 C8 C9 C5 2.05(16) . . . . ?
B1 C8 C9 C10 -177.70(13) . . . . ?
B1 C8 C13 C12 177.09(15) . . . . ?
B1 C16 C17 C18 179.35(14) . . . . ?
B1 C16 C21 C20 -178.29(12) . . . . ?
B1 C16 C21 C22 2.23(15) . . . . ?
B2 N2 C40 C39 -2.41(14) . . . . ?
B2 N2 C40 C41 177.62(12) . . . . ?
B2 N2 C44 C43 -177.75(13) . . . . ?
B2 C28 C39 C38 -175.99(11) . . . . ?
B2 C28 C39 C40 3.04(14) . . . . ?
B2 C29 C30 C31 -179.93(14) . . . . ?
B2 C29 C35 C34 179.05(13) . . . . ?
B2 C29 C35 C36 -3.34(16) . . . . ?
B2 C37 C45 C46 179.28(15) . . . . ?
