#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/43/7104331.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_7104331
loop_
_publ_author_name
'Zhang, Lu'
'Kerszulis, Justin A'
'Clark, Ronald J'
'Ye, Tao'
'Zhu, Lei'
_publ_section_title
;
 Catechol boronate formation and its electrochemical oxidation.
;
_journal_issue                   16
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2151
_journal_page_last               2153
_journal_paper_doi               10.1039/b900016j
_journal_volume                  34
_journal_year                    2009
_chemical_formula_moiety         'C24 H24 B N O2'
_chemical_formula_sum            'C24 H24 B N O2'
_chemical_formula_weight         369.25
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.736(2)
_cell_angle_beta                 91.472(2)
_cell_angle_gamma                101.463(2)
_cell_formula_units_Z            4
_cell_length_a                   9.9127(3)
_cell_length_b                   10.3809(4)
_cell_length_c                   19.5778(7)
_cell_measurement_reflns_used    9050
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.71
_cell_measurement_theta_min      2.00
_cell_volume                     1972.48(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31551
_diffrn_reflns_theta_full        24.71
_diffrn_reflns_theta_max         24.71
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9816
_exptl_absorpt_correction_T_min  0.9158
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0075(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         6723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0369
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+0.3116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0929
_refine_ls_wR_factor_ref         0.1019
_reflns_number_gt                5170
_reflns_number_total             6723
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b900016j.txt
_cod_data_source_block           zhu20
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7104331
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.20810(14) 0.76003(13) 0.01679(7) 0.0298(3) Uani 1 1 d . . .
H1 H -0.1997 0.7848 0.0641 0.036 Uiso 1 1 calc R . .
C2 C -0.32346(15) 0.77190(14) -0.01906(8) 0.0347(4) Uani 1 1 d . . .
H2 H -0.3939 0.8052 0.0034 0.042 Uiso 1 1 calc R . .
C3 C -0.34051(16) 0.73553(14) -0.08932(8) 0.0375(4) Uani 1 1 d . . .
H3 H -0.4221 0.7440 -0.1138 0.045 Uiso 1 1 calc R . .
C4 C -0.24036(16) 0.68852(14) -0.12176(8) 0.0356(4) Uani 1 1 d . . .
H4 H -0.2528 0.6640 -0.1690 0.043 Uiso 1 1 calc R . .
C5 C -0.11647(15) 0.67509(13) -0.08640(7) 0.0292(3) Uani 1 1 d . . .
C6 C -0.01393(15) 0.62729(13) -0.12001(7) 0.0320(4) Uani 1 1 d . . .
H6 H -0.0265 0.6044 -0.1674 0.038 Uiso 1 1 calc R . .
C7 C 0.10690(15) 0.61193(13) -0.08620(7) 0.0290(3) Uani 1 1 d . . .
C8 C 0.21048(16) 0.55922(14) -0.12024(8) 0.0359(4) Uani 1 1 d . . .
H8 H 0.1971 0.5338 -0.1673 0.043 Uiso 1 1 calc R . .
C9 C 0.32743(17) 0.54460(15) -0.08689(8) 0.0402(4) Uani 1 1 d . . .
H9 H 0.3952 0.5093 -0.1105 0.048 Uiso 1 1 calc R . .
C10 C 0.34835(16) 0.58210(14) -0.01682(8) 0.0373(4) Uani 1 1 d . . .
H10 H 0.4310 0.5726 0.0063 0.045 Uiso 1 1 calc R . .
C11 C 0.25221(15) 0.63139(13) 0.01789(8) 0.0317(3) Uani 1 1 d . . .
H11 H 0.2687 0.6551 0.0651 0.038 Uiso 1 1 calc R . .
C12 C 0.12682(14) 0.64847(13) -0.01475(7) 0.0273(3) Uani 1 1 d . . .
C13 C 0.02396(14) 0.69715(13) 0.02046(7) 0.0259(3) Uani 1 1 d . . .
C14 C -0.09831(14) 0.71112(13) -0.01455(7) 0.0267(3) Uani 1 1 d . . .
C15 C 0.04619(14) 0.72682(13) 0.09667(7) 0.0271(3) Uani 1 1 d . . .
H15A H -0.0441 0.7268 0.1172 0.032 Uiso 1 1 calc R . .
H15B H 0.0851 0.6558 0.1174 0.032 Uiso 1 1 calc R . .
C16 C 0.06638(16) 0.96276(14) 0.10312(8) 0.0377(4) Uani 1 1 d . . .
H16A H 0.0307 0.9582 0.0558 0.057 Uiso 1 1 calc R . .
H16B H 0.1301 1.0470 0.1122 0.057 Uiso 1 1 calc R . .
H16C H -0.0103 0.9553 0.1343 0.057 Uiso 1 1 calc R . .
C17 C 0.19002(15) 0.85939(14) 0.18567(7) 0.0315(3) Uani 1 1 d . . .
H17A H 0.1102 0.8350 0.2153 0.038 Uiso 1 1 calc R . .
H17B H 0.2357 0.9509 0.1985 0.038 Uiso 1 1 calc R . .
C18 C 0.29019(14) 0.76976(14) 0.19935(7) 0.0284(3) Uani 1 1 d . . .
C19 C 0.24753(16) 0.65861(15) 0.23728(7) 0.0334(4) Uani 1 1 d . . .
H19 H 0.1554 0.6389 0.2521 0.040 Uiso 1 1 calc R . .
C20 C 0.33639(17) 0.57628(15) 0.25388(7) 0.0389(4) Uani 1 1 d . . .
H20 H 0.3049 0.5003 0.2793 0.047 Uiso 1 1 calc R . .
C21 C 0.47108(17) 0.60478(16) 0.23336(8) 0.0399(4) Uani 1 1 d . . .
H21 H 0.5333 0.5499 0.2454 0.048 Uiso 1 1 calc R . .
C22 C 0.51412(16) 0.71421(15) 0.19501(7) 0.0347(4) Uani 1 1 d . . .
H22 H 0.6067 0.7328 0.1808 0.042 Uiso 1 1 calc R . .
C23 C 0.42682(14) 0.79852(14) 0.17634(7) 0.0283(3) Uani 1 1 d . . .
C24 C 0.68549(16) 1.06501(15) 0.08889(8) 0.0391(4) Uani 1 1 d . . .
H24A H 0.6668 1.0372 0.0407 0.059 Uiso 1 1 calc R . .
H24B H 0.7852 1.0862 0.0982 0.059 Uiso 1 1 calc R . .
H24C H 0.6465 1.1430 0.0988 0.059 Uiso 1 1 calc R . .
B1 B 0.48455(17) 0.91425(16) 0.12794(8) 0.0288(4) Uani 1 1 d . . .
O1 O 0.40517(11) 0.96491(10) 0.08345(5) 0.0359(3) Uani 1 1 d . . .
H1O H 0.3134(17) 0.9236(16) 0.0843(8) 0.043 Uiso 1 1 d . . .
O2 O 0.62377(10) 0.96035(9) 0.13147(5) 0.0337(3) Uani 1 1 d . . .
N1 N 0.13924(11) 0.85451(11) 0.11375(6) 0.0277(3) Uani 1 1 d . . .
C31 C 0.66192(16) 0.32148(15) 0.46588(7) 0.0378(4) Uani 1 1 d . . .
H31 H 0.7252 0.3097 0.4317 0.045 Uiso 1 1 calc R . .
C32 C 0.69372(19) 0.42614(16) 0.51060(8) 0.0456(4) Uani 1 1 d . . .
H32 H 0.7784 0.4868 0.5070 0.055 Uiso 1 1 calc R . .
C33 C 0.6029(2) 0.44615(17) 0.56226(8) 0.0491(5) Uani 1 1 d . . .
H33 H 0.6262 0.5206 0.5928 0.059 Uiso 1 1 calc R . .
C34 C 0.48316(19) 0.36017(17) 0.56849(8) 0.0442(4) Uani 1 1 d . . .
H34 H 0.4235 0.3741 0.6040 0.053 Uiso 1 1 calc R . .
C35 C 0.44435(16) 0.24854(15) 0.52269(7) 0.0358(4) Uani 1 1 d . . .
C36 C 0.32260(16) 0.15781(16) 0.52904(7) 0.0381(4) Uani 1 1 d . . .
H36 H 0.2630 0.1711 0.5647 0.046 Uiso 1 1 calc R . .
C37 C 0.28460(15) 0.04821(15) 0.48521(7) 0.0334(4) Uani 1 1 d . . .
C38 C 0.16068(16) -0.04594(16) 0.49425(8) 0.0401(4) Uani 1 1 d . . .
H38 H 0.1033 -0.0330 0.5309 0.048 Uiso 1 1 calc R . .
C39 C 0.12313(16) -0.15296(17) 0.45186(8) 0.0425(4) Uani 1 1 d . . .
H39 H 0.0405 -0.2146 0.4589 0.051 Uiso 1 1 calc R . .
C40 C 0.20741(16) -0.17264(16) 0.39709(8) 0.0396(4) Uani 1 1 d . . .
H40 H 0.1804 -0.2476 0.3672 0.047 Uiso 1 1 calc R . .
C41 C 0.32632(15) -0.08642(15) 0.38639(7) 0.0337(4) Uani 1 1 d . . .
H41 H 0.3805 -0.1023 0.3489 0.040 Uiso 1 1 calc R . .
C42 C 0.37263(15) 0.02814(14) 0.43008(7) 0.0299(3) Uani 1 1 d . . .
C43 C 0.49724(15) 0.11884(14) 0.42262(7) 0.0300(3) Uani 1 1 d . . .
C44 C 0.53489(15) 0.22852(14) 0.46910(7) 0.0324(4) Uani 1 1 d . . .
C45 C 0.59639(15) 0.09951(14) 0.36764(7) 0.0316(3) Uani 1 1 d . . .
H45A H 0.6896 0.1076 0.3889 0.038 Uiso 1 1 calc R . .
H45B H 0.5684 0.0093 0.3474 0.038 Uiso 1 1 calc R . .
C46 C 0.47130(16) 0.17596(17) 0.27369(8) 0.0435(4) Uani 1 1 d . . .
H46A H 0.4757 0.2443 0.2399 0.065 Uiso 1 1 calc R . .
H46B H 0.3973 0.1817 0.3052 0.065 Uiso 1 1 calc R . .
H46C H 0.4529 0.0892 0.2502 0.065 Uiso 1 1 calc R . .
C47 C 0.71394(15) 0.17882(16) 0.26527(7) 0.0363(4) Uani 1 1 d . . .
H47A H 0.7107 0.2358 0.2259 0.044 Uiso 1 1 calc R . .
H47B H 0.6971 0.0865 0.2475 0.044 Uiso 1 1 calc R . .
C48 C 0.85587(15) 0.21291(15) 0.29921(7) 0.0336(4) Uani 1 1 d . . .
C49 C 0.93020(17) 0.11333(16) 0.30693(8) 0.0438(4) Uani 1 1 d . . .
H49 H 0.8913 0.0269 0.2899 0.053 Uiso 1 1 calc R . .
C50 C 1.05926(18) 0.13724(18) 0.33880(10) 0.0527(5) Uani 1 1 d . . .
H50 H 1.1077 0.0677 0.3439 0.063 Uiso 1 1 calc R . .
C51 C 1.11709(18) 0.26208(18) 0.36308(10) 0.0522(5) Uani 1 1 d . . .
H51 H 1.2047 0.2789 0.3860 0.063 Uiso 1 1 calc R . .
C52 C 1.04678(16) 0.36321(17) 0.35385(8) 0.0419(4) Uani 1 1 d . . .
H52 H 1.0892 0.4497 0.3694 0.050 Uiso 1 1 calc R . .
C53 C 0.91543(15) 0.34259(15) 0.32243(7) 0.0334(4) Uani 1 1 d . . .
C54 C 0.86628(18) 0.69780(16) 0.30227(9) 0.0485(4) Uani 1 1 d . . .
H54A H 0.8402 0.7051 0.2541 0.073 Uiso 1 1 calc R . .
H54B H 0.9334 0.7766 0.3176 0.073 Uiso 1 1 calc R . .
H54C H 0.7843 0.6895 0.3300 0.073 Uiso 1 1 calc R . .
B31 B 0.84191(18) 0.46313(17) 0.31505(8) 0.0323(4) Uani 1 1 d . . .
O31 O 0.70428(10) 0.45409(11) 0.31365(5) 0.0363(3) Uani 1 1 d . . .
H31O H 0.6567(16) 0.3697(17) 0.3205(8) 0.044 Uiso 1 1 d . . .
O32 O 0.92615(10) 0.58419(10) 0.30968(6) 0.0416(3) Uani 1 1 d . . .
N31 N 0.60294(12) 0.19490(12) 0.31223(6) 0.0316(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_
_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 C1 C14 121.88(14) . . ?
C2 C1 H1 119.1 . . ?
C14 C1 H1 119.1 . . ?
C1 C2 C3 120.96(15) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 119.89(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.30(14) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 121.03(13) . . ?
C6 C5 C14 119.67(13) . . ?
C4 C5 C14 119.29(13) . . ?
C5 C6 C7 121.88(13) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C6 C7 C8 121.90(13) . . ?
C6 C7 C12 119.02(13) . . ?
C8 C7 C12 119.07(13) . . ?
C9 C8 C7 121.42(14) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 119.71(14) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 121.01(15) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.57(14) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C13 C12 C11 122.71(13) . . ?
C13 C12 C7 120.07(13) . . ?
C11 C12 C7 117.21(13) . . ?
C12 C13 C14 120.10(12) . . ?
C12 C13 C15 118.05(12) . . ?
C14 C13 C15 121.77(12) . . ?
C13 C14 C1 124.08(13) . . ?
C13 C14 C5 119.24(13) . . ?
C1 C14 C5 116.67(12) . . ?
N1 C15 C13 113.53(11) . . ?
N1 C15 H15A 108.9 . . ?
C13 C15 H15A 108.9 . . ?
N1 C15 H15B 108.9 . . ?
C13 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C17 C18 114.05(11) . . ?
N1 C17 H17A 108.7 . . ?
C18 C17 H17A 108.7 . . ?
N1 C17 H17B 108.7 . . ?
C18 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C23 119.47(13) . . ?
C19 C18 C17 118.85(13) . . ?
C23 C18 C17 121.65(13) . . ?
C20 C19 C18 121.40(14) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 119.88(14) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 119.19(15) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C23 122.58(15) . . ?
C21 C22 H22 118.7 . . ?
C23 C22 H22 118.7 . . ?
C22 C23 C18 117.45(13) . . ?
C22 C23 B1 117.91(13) . . ?
C18 C23 B1 124.55(13) . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O1 B1 O2 120.00(14) . . ?
O1 B1 C23 123.59(13) . . ?
O2 B1 C23 116.38(13) . . ?
B1 O1 H1O 112.3(10) . . ?
B1 O2 C24 120.20(12) . . ?
C16 N1 C17 109.46(11) . . ?
C16 N1 C15 110.08(11) . . ?
C17 N1 C15 110.48(10) . . ?
C32 C31 C44 121.26(15) . . ?
C32 C31 H31 119.4 . . ?
C44 C31 H31 119.4 . . ?
C31 C32 C33 120.94(16) . . ?
C31 C32 H32 119.5 . . ?
C33 C32 H32 119.5 . . ?
C34 C33 C32 120.25(16) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 121.14(16) . . ?
C33 C34 H34 119.4 . . ?
C35 C34 H34 119.4 . . ?
C36 C35 C34 121.93(15) . . ?
C36 C35 C44 119.00(14) . . ?
C34 C35 C44 119.06(15) . . ?
C35 C36 C37 122.37(14) . . ?
C35 C36 H36 118.8 . . ?
C37 C36 H36 118.8 . . ?
C36 C37 C38 121.20(14) . . ?
C36 C37 C42 119.42(14) . . ?
C38 C37 C42 119.38(14) . . ?
C39 C38 C37 121.54(15) . . ?
C39 C38 H38 119.2 . . ?
C37 C38 H38 119.2 . . ?
C38 C39 C40 119.60(15) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C41 C40 C39 121.18(15) . . ?
C41 C40 H40 119.4 . . ?
C39 C40 H40 119.4 . . ?
C40 C41 C42 121.87(14) . . ?
C40 C41 H41 119.1 . . ?
C42 C41 H41 119.1 . . ?
C43 C42 C41 124.27(13) . . ?
C43 C42 C37 119.31(13) . . ?
C41 C42 C37 116.42(13) . . ?
C42 C43 C44 120.04(13) . . ?
C42 C43 C45 121.55(13) . . ?
C44 C43 C45 118.36(13) . . ?
C43 C44 C31 122.85(14) . . ?
C43 C44 C35 119.83(14) . . ?
C31 C44 C35 117.31(14) . . ?
N31 C45 C43 113.55(12) . . ?
N31 C45 H45A 108.9 . . ?
C43 C45 H45A 108.9 . . ?
N31 C45 H45B 108.9 . . ?
C43 C45 H45B 108.9 . . ?
H45A C45 H45B 107.7 . . ?
N31 C46 H46A 109.5 . . ?
N31 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
N31 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
N31 C47 C48 112.97(11) . . ?
N31 C47 H47A 109.0 . . ?
C48 C47 H47A 109.0 . . ?
N31 C47 H47B 109.0 . . ?
C48 C47 H47B 109.0 . . ?
H47A C47 H47B 107.8 . . ?
C49 C48 C53 119.37(14) . . ?
C49 C48 C47 118.64(14) . . ?
C53 C48 C47 121.98(13) . . ?
C50 C49 C48 121.58(16) . . ?
C50 C49 H49 119.2 . . ?
C48 C49 H49 119.2 . . ?
C51 C50 C49 119.70(16) . . ?
C51 C50 H50 120.1 . . ?
C49 C50 H50 120.1 . . ?
C50 C51 C52 119.55(16) . . ?
C50 C51 H51 120.2 . . ?
C52 C51 H51 120.2 . . ?
C51 C52 C53 122.36(16) . . ?
C51 C52 H52 118.8 . . ?
C53 C52 H52 118.8 . . ?
C52 C53 C48 117.38(14) . . ?
C52 C53 B31 118.96(14) . . ?
C48 C53 B31 123.66(13) . . ?
O32 C54 H54A 109.5 . . ?
O32 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
O32 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O31 B31 O32 119.12(14) . . ?
O31 B31 C53 124.42(14) . . ?
O32 B31 C53 116.46(13) . . ?
B31 O31 H31O 112.7(10) . . ?
B31 O32 C54 119.44(12) . . ?
C46 N31 C47 109.58(11) . . ?
C46 N31 C45 110.98(11) . . ?
C47 N31 C45 109.73(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
C1 C2 1.355(2) . ?
C1 C14 1.433(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.412(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.354(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.427(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(2) . ?
C5 C14 1.4421(19) . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.426(2) . ?
C7 C12 1.4365(19) . ?
C8 C9 1.353(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.413(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.356(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.428(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.411(2) . ?
C13 C14 1.4117(19) . ?
C13 C15 1.5158(18) . ?
C15 N1 1.4802(17) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N1 1.4686(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 N1 1.4791(17) . ?
C17 C18 1.514(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.391(2) . ?
C18 C23 1.416(2) . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.383(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.397(2) . ?
C22 H22 0.9500 . ?
C23 B1 1.579(2) . ?
C24 O2 1.4376(17) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
B1 O1 1.3459(19) . ?
B1 O2 1.3672(19) . ?
O1 H1O 0.926(17) . ?
C31 C32 1.356(2) . ?
C31 C44 1.430(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.409(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.347(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.427(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.386(2) . ?
C35 C44 1.435(2) . ?
C36 C37 1.388(2) . ?
C36 H36 0.9500 . ?
C37 C38 1.428(2) . ?
C37 C42 1.441(2) . ?
C38 C39 1.351(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.411(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.356(2) . ?
C40 H40 0.9500 . ?
C41 C42 1.435(2) . ?
C41 H41 0.9500 . ?
C42 C43 1.410(2) . ?
C43 C44 1.419(2) . ?
C43 C45 1.511(2) . ?
C45 N31 1.4848(18) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C46 N31 1.4660(18) . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
C47 N31 1.4830(19) . ?
C47 C48 1.512(2) . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?
C48 C49 1.393(2) . ?
C48 C53 1.415(2) . ?
C49 C50 1.382(2) . ?
C49 H49 0.9500 . ?
C50 C51 1.374(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.384(2) . ?
C51 H51 0.9500 . ?
C52 C53 1.400(2) . ?
C52 H52 0.9500 . ?
C53 B31 1.577(2) . ?
C54 O32 1.4312(19) . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
B31 O31 1.348(2) . ?
B31 O32 1.372(2) . ?
O31 H31O 0.924(17) . ?
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
C14 C1 C2 C3 0.3(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C3 C4 C5 C6 -179.75(13) . . . . ?
C3 C4 C5 C14 0.6(2) . . . . ?
C4 C5 C6 C7 -179.18(13) . . . . ?
C14 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C8 178.13(13) . . . . ?
C5 C6 C7 C12 -1.0(2) . . . . ?
C6 C7 C8 C9 -179.94(14) . . . . ?
C12 C7 C8 C9 -0.9(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 178.75(13) . . . . ?
C10 C11 C12 C7 -0.4(2) . . . . ?
C6 C7 C12 C13 1.00(19) . . . . ?
C8 C7 C12 C13 -178.12(12) . . . . ?
C6 C7 C12 C11 -179.87(12) . . . . ?
C8 C7 C12 C11 1.01(19) . . . . ?
C11 C12 C13 C14 -179.61(12) . . . . ?
C7 C12 C13 C14 -0.53(19) . . . . ?
C11 C12 C13 C15 -2.59(19) . . . . ?
C7 C12 C13 C15 176.49(11) . . . . ?
C12 C13 C14 C1 -179.77(12) . . . . ?
C15 C13 C14 C1 3.3(2) . . . . ?
C12 C13 C14 C5 0.02(19) . . . . ?
C15 C13 C14 C5 -176.89(12) . . . . ?
C2 C1 C14 C13 179.85(13) . . . . ?
C2 C1 C14 C5 0.06(19) . . . . ?
C6 C5 C14 C13 0.04(19) . . . . ?
C4 C5 C14 C13 179.67(12) . . . . ?
C6 C5 C14 C1 179.84(12) . . . . ?
C4 C5 C14 C1 -0.52(18) . . . . ?
C12 C13 C15 N1 79.89(15) . . . . ?
C14 C13 C15 N1 -103.14(14) . . . . ?
N1 C17 C18 C19 -109.27(14) . . . . ?
N1 C17 C18 C23 72.71(17) . . . . ?
C23 C18 C19 C20 0.9(2) . . . . ?
C17 C18 C19 C20 -177.17(13) . . . . ?
C18 C19 C20 C21 0.8(2) . . . . ?
C19 C20 C21 C22 -1.4(2) . . . . ?
C20 C21 C22 C23 0.5(2) . . . . ?
C21 C22 C23 C18 1.2(2) . . . . ?
C21 C22 C23 B1 -175.57(13) . . . . ?
C19 C18 C23 C22 -1.83(19) . . . . ?
C17 C18 C23 C22 176.18(12) . . . . ?
C19 C18 C23 B1 174.69(12) . . . . ?
C17 C18 C23 B1 -7.3(2) . . . . ?
C22 C23 B1 O1 150.26(14) . . . . ?
C18 C23 B1 O1 -26.2(2) . . . . ?
C22 C23 B1 O2 -27.80(19) . . . . ?
C18 C23 B1 O2 155.70(13) . . . . ?
O1 B1 O2 C24 1.4(2) . . . . ?
C23 B1 O2 C24 179.57(12) . . . . ?
C18 C17 N1 C16 -168.60(12) . . . . ?
C18 C17 N1 C15 70.03(15) . . . . ?
C13 C15 N1 C16 76.31(14) . . . . ?
C13 C15 N1 C17 -162.69(11) . . . . ?
C44 C31 C32 C33 0.6(2) . . . . ?
C31 C32 C33 C34 0.8(3) . . . . ?
C32 C33 C34 C35 -1.0(2) . . . . ?
C33 C34 C35 C36 178.88(15) . . . . ?
C33 C34 C35 C44 -0.2(2) . . . . ?
C34 C35 C36 C37 -179.32(14) . . . . ?
C44 C35 C36 C37 -0.3(2) . . . . ?
C35 C36 C37 C38 177.97(14) . . . . ?
C35 C36 C37 C42 -1.2(2) . . . . ?
C36 C37 C38 C39 -179.90(15) . . . . ?
C42 C37 C38 C39 -0.7(2) . . . . ?
C37 C38 C39 C40 -0.3(2) . . . . ?
C38 C39 C40 C41 0.5(2) . . . . ?
C39 C40 C41 C42 0.3(2) . . . . ?
C40 C41 C42 C43 178.00(14) . . . . ?
C40 C41 C42 C37 -1.2(2) . . . . ?
C36 C37 C42 C43 1.3(2) . . . . ?
C38 C37 C42 C43 -177.87(13) . . . . ?
C36 C37 C42 C41 -179.40(13) . . . . ?
C38 C37 C42 C41 1.38(19) . . . . ?
C41 C42 C43 C44 -179.19(13) . . . . ?
C37 C42 C43 C44 0.0(2) . . . . ?
C41 C42 C43 C45 -1.9(2) . . . . ?
C37 C42 C43 C45 177.31(12) . . . . ?
C42 C43 C44 C31 177.72(13) . . . . ?
C45 C43 C44 C31 0.3(2) . . . . ?
C42 C43 C44 C35 -1.5(2) . . . . ?
C45 C43 C44 C35 -178.87(12) . . . . ?
C32 C31 C44 C43 179.11(14) . . . . ?
C32 C31 C44 C35 -1.7(2) . . . . ?
C36 C35 C44 C43 1.6(2) . . . . ?
C34 C35 C44 C43 -179.29(13) . . . . ?
C36 C35 C44 C31 -177.63(13) . . . . ?
C34 C35 C44 C31 1.5(2) . . . . ?
C42 C43 C45 N31 109.57(15) . . . . ?
C44 C43 C45 N31 -73.07(16) . . . . ?
N31 C47 C48 C49 114.54(15) . . . . ?
N31 C47 C48 C53 -66.22(18) . . . . ?
C53 C48 C49 C50 2.1(2) . . . . ?
C47 C48 C49 C50 -178.60(14) . . . . ?
C48 C49 C50 C51 -0.6(3) . . . . ?
C49 C50 C51 C52 -1.6(3) . . . . ?
C50 C51 C52 C53 2.2(3) . . . . ?
C51 C52 C53 C48 -0.7(2) . . . . ?
C51 C52 C53 B31 179.06(15) . . . . ?
C49 C48 C53 C52 -1.5(2) . . . . ?
C47 C48 C53 C52 179.29(13) . . . . ?
C49 C48 C53 B31 178.80(14) . . . . ?
C47 C48 C53 B31 -0.4(2) . . . . ?
C52 C53 B31 O31 -150.87(15) . . . . ?
C48 C53 B31 O31 28.8(2) . . . . ?
C52 C53 B31 O32 29.2(2) . . . . ?
C48 C53 B31 O32 -151.05(14) . . . . ?
O31 B31 O32 C54 -0.4(2) . . . . ?
C53 B31 O32 C54 179.48(13) . . . . ?
C48 C47 N31 C46 173.04(13) . . . . ?
C48 C47 N31 C45 -64.86(15) . . . . ?
C43 C45 N31 C46 -65.40(16) . . . . ?
C43 C45 N31 C47 173.35(12) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139180981
