#------------------------------------------------------------------------------
#$Date: 2024-06-06 01:51:13 +0300 (Thu, 06 Jun 2024) $
#$Revision: 292210 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/63/7716311.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_7716311
loop_
_publ_author_name
'Dunes, Gabriel'
'Cordier, Marie'
'Kahlal, Samia'
'Pollnitz, Alpar'
'Saillard, Jean-Yves'
'Silvestru, Cristian'
'Sarazin, Yann'
_publ_section_title
;
 C--H Bond Activation at Antimony(III): Synthesis and Reactivity of
 Sb(III)-Oxyaryl Species
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D4DT01400F
_journal_year                    2024
_chemical_formula_moiety         'C34 H55 N2 O Sb'
_chemical_formula_sum            'C34 H55 N2 O Sb'
_chemical_formula_weight         629.55
_chemical_name_common            DG167
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2024-02-28 deposited with the CCDC.	2024-05-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.8090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7653(3)
_cell_length_b                   21.1742(7)
_cell_length_c                   15.8732(5)
_cell_measurement_reflns_used    9880
_cell_measurement_temperature    110.(2)
_cell_measurement_theta_max      28.2772
_cell_measurement_theta_min      2.3253
_cell_volume                     3223.91(18)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker APEX4 2022.10-0'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1503)'
_computing_publication_material  'Bruker APEX4 2022.10-0'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      110.(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_device_type  'three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            99732
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    0.883
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7997
_refine_ls_number_restraints     178
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0192
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0140P)²+2.2185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0418
_refine_ls_wR_factor_ref         0.0440
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7161
_reflns_number_total             7997
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt01400f3.cif
_cod_data_source_block           4
_cod_database_code               7716311
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sb Sb1 0.29284(2) 0.41547(2) 0.68830(2) 0.01232(3) Uani d . . . 1.000000 . .
O O1 0.37167(12) 0.70417(5) 0.65701(8) 0.0283(2) Uani d . . . 1.000000 . .
N N1 0.19965(12) 0.44569(6) 0.82231(7) 0.0167(2) Uani d . . D 1.000000 . .
N N2 0.46721(12) 0.34777(5) 0.62543(7) 0.0142(2) Uani d . . . 1.000000 . .
C C1 0.45592(14) 0.39390(6) 0.79273(8) 0.0142(3) Uani d . . . 1.000000 . .
C C2 0.44990(14) 0.42064(6) 0.87244(9) 0.0162(3) Uani d . . . 1.000000 . .
C C3 0.55472(16) 0.40785(7) 0.94248(9) 0.0212(3) Uani d . . . 1.000000 . .
H H3 0.550896 0.425571 0.996968 0.025000 Uiso calc U . R 1.000000 . .
C C4 0.66536(16) 0.36894(7) 0.93239(10) 0.0237(3) Uani d . . . 1.000000 . .
H H4 0.738287 0.361084 0.979919 0.028000 Uiso calc U . R 1.000000 . .
C C5 0.67024(15) 0.34155(7) 0.85380(10) 0.0205(3) Uani d . . . 1.000000 . .
H H5 0.745566 0.314577 0.847826 0.025000 Uiso calc U . R 1.000000 . .
C C6 0.56421(14) 0.35361(6) 0.78316(9) 0.0162(3) Uani d . . . 1.000000 . .
C C7 0.33129(14) 0.46458(7) 0.87971(9) 0.0178(3) Uani d . . . 1.000000 . .
H H7A 0.316752 0.464865 0.939779 0.021000 Uiso calc U . R 1.000000 . .
H H7B 0.356236 0.507994 0.865020 0.021000 Uiso calc U . R 1.000000 . .
C C8A 0.10768(17) 0.50347(8) 0.80370(11) 0.0208(4) Uani d U P D 0.916(3) A 1
H H8A 0.162860 0.534239 0.775826 0.025000 Uiso calc U P R 0.916(3) A 1
C C9A -0.02474(16) 0.49177(8) 0.73825(11) 0.0220(4) Uani d U P D 0.916(3) A 1
H H9AA -0.064795 0.532278 0.716150 0.033000 Uiso calc U P R 0.916(3) A 1
H H9AB -0.092087 0.468983 0.765573 0.033000 Uiso calc U P R 0.916(3) A 1
H H9AC -0.002737 0.466490 0.690803 0.033000 Uiso calc U P R 0.916(3) A 1
C C10A 0.0725(2) 0.53826(12) 0.88138(13) 0.0431(6) Uani d U P D 0.916(3) A 1
H H10A 0.031321 0.579409 0.863254 0.065000 Uiso calc U P R 0.916(3) A 1
H H10B 0.157829 0.544462 0.924187 0.065000 Uiso calc U P R 0.916(3) A 1
H H10C 0.005924 0.513207 0.906480 0.065000 Uiso calc U P R 0.916(3) A 1
C C11A 0.1421(8) 0.3866(3) 0.8549(3) 0.0266(11) Uani d U P D 0.754(4) A 1
H H11A 0.222953 0.357124 0.869913 0.032000 Uiso calc U P R 0.754(4) A 1
C C12A 0.0343(13) 0.3516(8) 0.7903(4) 0.0273(10) Uani d U P D 0.754(4) A 1
H H12A 0.028758 0.307658 0.808709 0.041000 Uiso calc U P R 0.754(4) A 1
H H12B 0.061487 0.352692 0.733969 0.041000 Uiso calc U P R 0.754(4) A 1
H H12C -0.056798 0.371897 0.786648 0.041000 Uiso calc U P R 0.754(4) A 1
C C13A 0.0855(3) 0.39628(16) 0.93834(16) 0.0434(7) Uani d U P D 0.754(4) A 1
H H13A 0.075051 0.355179 0.964785 0.065000 Uiso calc U P R 0.754(4) A 1
H H13B -0.005277 0.417397 0.925190 0.065000 Uiso calc U P R 0.754(4) A 1
H H13C 0.150864 0.422418 0.978090 0.065000 Uiso calc U P R 0.754(4) A 1
C C8B 0.0776(17) 0.4870(8) 0.8256(12) 0.0208(4) Uani d U P D 0.084(3) A 2
H H8B 0.003124 0.476853 0.775116 0.025000 Uiso calc U P R 0.084(3) A 2
C C9B 0.012(2) 0.4867(11) 0.9057(12) 0.0431(6) Uani d U P D 0.084(3) A 2
H H9BA -0.057659 0.520351 0.901381 0.065000 Uiso calc U P R 0.084(3) A 2
H H9BB 0.084737 0.493684 0.956473 0.065000 Uiso calc U P R 0.084(3) A 2
H H9BC -0.032642 0.445774 0.910544 0.065000 Uiso calc U P R 0.084(3) A 2
C C10B 0.129(2) 0.5533(8) 0.8141(13) 0.030(4) Uani d U P D 0.084(3) A 2
H H10D 0.049674 0.580710 0.791924 0.046000 Uiso calc U P R 0.084(3) A 2
H H10E 0.193266 0.552593 0.773441 0.046000 Uiso calc U P R 0.084(3) A 2
H H10F 0.177899 0.569547 0.869479 0.046000 Uiso calc U P R 0.084(3) A 2
C C11B 0.158(3) 0.3798(9) 0.8502(10) 0.0266(11) Uani d U P D 0.246(4) A 2
H H11B 0.232996 0.351936 0.835674 0.032000 Uiso calc U P R 0.246(4) A 2
C C12B 0.026(4) 0.353(3) 0.7954(15) 0.0273(10) Uani d U P D 0.246(4) A 2
H H12D 0.025944 0.306575 0.801208 0.041000 Uiso calc U P R 0.246(4) A 2
H H12E 0.022220 0.363924 0.735150 0.041000 Uiso calc U P R 0.246(4) A 2
H H12F -0.056241 0.370055 0.814696 0.041000 Uiso calc U P R 0.246(4) A 2
C C13B 0.1597(10) 0.3644(5) 0.9439(5) 0.0434(7) Uani d U P D 0.246(4) A 2
H H13D 0.133072 0.320186 0.949120 0.065000 Uiso calc U P R 0.246(4) A 2
H H13E 0.093403 0.391855 0.965754 0.065000 Uiso calc U P R 0.246(4) A 2
H H13F 0.253574 0.371362 0.977229 0.065000 Uiso calc U P R 0.246(4) A 2
C C14 0.56266(15) 0.31889(7) 0.69970(9) 0.0188(3) Uani d . . . 1.000000 . .
H H14A 0.658397 0.318226 0.687459 0.023000 Uiso calc U . R 1.000000 . .
H H14B 0.533859 0.274613 0.706283 0.023000 Uiso calc U . R 1.000000 . .
C C15 0.37885(14) 0.29750(6) 0.57319(9) 0.0172(3) Uani d . . . 1.000000 . .
H H15 0.309621 0.320041 0.528941 0.021000 Uiso calc U . R 1.000000 . .
C C16 0.46223(16) 0.25370(7) 0.52481(10) 0.0222(3) Uani d . . . 1.000000 . .
H H16A 0.400836 0.220572 0.495769 0.033000 Uiso calc U . R 1.000000 . .
H H16B 0.538605 0.234346 0.565479 0.033000 Uiso calc U . R 1.000000 . .
H H16C 0.500584 0.278174 0.482234 0.033000 Uiso calc U . R 1.000000 . .
C C17 0.29549(17) 0.25786(7) 0.62631(11) 0.0257(3) Uani d . . . 1.000000 . .
H H17A 0.217222 0.237648 0.588158 0.038000 Uiso calc U . R 1.000000 . .
H H17B 0.259801 0.285152 0.667145 0.038000 Uiso calc U . R 1.000000 . .
H H17C 0.355994 0.225355 0.657680 0.038000 Uiso calc U . R 1.000000 . .
C C18 0.54937(14) 0.38413(7) 0.56963(9) 0.0176(3) Uani d . . . 1.000000 . .
H H18 0.608150 0.353039 0.544985 0.021000 Uiso calc U . R 1.000000 . .
C C19 0.45381(16) 0.41596(7) 0.49500(9) 0.0218(3) Uani d . . . 1.000000 . .
H H19A 0.509885 0.440430 0.461494 0.033000 Uiso calc U . R 1.000000 . .
H H19B 0.389345 0.444228 0.517107 0.033000 Uiso calc U . R 1.000000 . .
H H19C 0.400639 0.383747 0.458336 0.033000 Uiso calc U . R 1.000000 . .
C C20 0.64715(15) 0.43235(7) 0.62062(10) 0.0222(3) Uani d . . . 1.000000 . .
H H20A 0.704196 0.451988 0.583186 0.033000 Uiso calc U . R 1.000000 . .
H H20B 0.707917 0.411182 0.668448 0.033000 Uiso calc U . R 1.000000 . .
H H20C 0.592267 0.464899 0.643027 0.033000 Uiso calc U . R 1.000000 . .
C C21 0.34106(14) 0.51014(6) 0.67130(8) 0.0137(2) Uani d . . . 1.000000 . .
C C22 0.23480(14) 0.54615(7) 0.62091(9) 0.0155(3) Uani d . . . 1.000000 . .
H H22 0.158107 0.524692 0.587274 0.019000 Uiso calc U . R 1.000000 . .
C C23 0.23750(14) 0.61134(7) 0.61837(9) 0.0160(3) Uani d . . . 1.000000 . .
C C24 0.35953(15) 0.64481(7) 0.66378(9) 0.0177(3) Uani d . . . 1.000000 . .
C C25 0.46639(14) 0.60744(6) 0.71858(8) 0.0147(3) Uani d . . . 1.000000 . .
C C26 0.45333(13) 0.54267(6) 0.72086(8) 0.0138(2) Uani d . . . 1.000000 . .
H H26 0.523111 0.519092 0.757441 0.017000 Uiso calc U . R 1.000000 . .
C C27 0.10962(15) 0.64907(7) 0.57376(9) 0.0196(3) Uani d . . . 1.000000 . .
C C28 0.14257(18) 0.69240(9) 0.50231(11) 0.0320(4) Uani d . . . 1.000000 . .
H H28A 0.061293 0.718849 0.480528 0.048000 Uiso calc U . R 1.000000 . .
H H28B 0.165057 0.666560 0.455518 0.048000 Uiso calc U . R 1.000000 . .
H H28C 0.222357 0.719369 0.525399 0.048000 Uiso calc U . R 1.000000 . .
C C29 0.05751(17) 0.68979(8) 0.64153(11) 0.0292(4) Uani d . . . 1.000000 . .
H H29A -0.025536 0.713329 0.614427 0.044000 Uiso calc U . R 1.000000 . .
H H29B 0.130782 0.719497 0.666724 0.044000 Uiso calc U . R 1.000000 . .
H H29C 0.034076 0.662477 0.686614 0.044000 Uiso calc U . R 1.000000 . .
C C30 -0.01062(16) 0.60612(8) 0.53260(11) 0.0296(4) Uani d . . . 1.000000 . .
H H30A -0.089838 0.632066 0.505507 0.044000 Uiso calc U . R 1.000000 . .
H H30B -0.038794 0.579395 0.576792 0.044000 Uiso calc U . R 1.000000 . .
H H30C 0.019821 0.579416 0.489161 0.044000 Uiso calc U . R 1.000000 . .
C C31 0.59129(14) 0.64087(7) 0.77387(9) 0.0173(3) Uani d . . . 1.000000 . .
C C32 0.67802(16) 0.67558(8) 0.71676(10) 0.0263(3) Uani d . . . 1.000000 . .
H H32A 0.753354 0.699097 0.752931 0.039000 Uiso calc U . R 1.000000 . .
H H32B 0.618031 0.704981 0.678872 0.039000 Uiso calc U . R 1.000000 . .
H H32C 0.717912 0.644761 0.682115 0.039000 Uiso calc U . R 1.000000 . .
C C33 0.54046(18) 0.68829(8) 0.83441(11) 0.0279(3) Uani d . . . 1.000000 . .
H H33A 0.620677 0.710514 0.867816 0.042000 Uiso calc U . R 1.000000 . .
H H33B 0.490661 0.665731 0.873386 0.042000 Uiso calc U . R 1.000000 . .
H H33C 0.477609 0.718901 0.800663 0.042000 Uiso calc U . R 1.000000 . .
C C34 0.68915(16) 0.59460(7) 0.82989(10) 0.0256(3) Uani d . . . 1.000000 . .
H H34A 0.766988 0.617926 0.863996 0.038000 Uiso calc U . R 1.000000 . .
H H34B 0.725247 0.563977 0.793230 0.038000 Uiso calc U . R 1.000000 . .
H H34C 0.637832 0.572299 0.868298 0.038000 Uiso calc U . R 1.000000 . .
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'
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'
Sb Sb -0.5866 1.5461 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21 Sb1 C1 . . 98.81(5) ?
C21 Sb1 N1 . . 89.51(4) ?
C1 Sb1 N1 . . 74.64(5) ?
C21 Sb1 N2 . . 107.68(4) ?
C1 Sb1 N2 . . 74.22(4) ?
N1 Sb1 N2 . . 146.30(4) ?
C7 N1 C8B . . 115.3(8) ?
C7 N1 C11A . . 110.5(3) ?
C7 N1 C8A . . 108.41(11) ?
C11A N1 C8A . . 119.6(3) ?
C7 N1 C11B . . 108.2(9) ?
C8B N1 C11B . . 105.5(13) ?
C7 N1 Sb1 . . 100.16(8) ?
C8B N1 Sb1 . . 126.3(7) ?
C11A N1 Sb1 . . 107.1(2) ?
C8A N1 Sb1 . . 109.38(9) ?
C11B N1 Sb1 . . 99.6(8) ?
C14 N2 C18 . . 110.51(11) ?
C14 N2 C15 . . 110.62(11) ?
C18 N2 C15 . . 110.31(10) ?
C14 N2 Sb1 . . 106.48(8) ?
C18 N2 Sb1 . . 114.01(8) ?
C15 N2 Sb1 . . 104.70(7) ?
C6 C1 C2 . . 120.67(12) ?
C6 C1 Sb1 . . 121.47(10) ?
C2 C1 Sb1 . . 117.85(10) ?
C3 C2 C1 . . 119.71(13) ?
C3 C2 C7 . . 121.38(13) ?
C1 C2 C7 . . 118.88(12) ?
C2 C3 C4 . . 119.66(14) ?
C2 C3 H3 . . 120.200000 ?
C4 C3 H3 . . 120.200000 ?
C5 C4 C3 . . 120.68(13) ?
C5 C4 H4 . . 119.700000 ?
C3 C4 H4 . . 119.700000 ?
C4 C5 C6 . . 120.01(13) ?
C4 C5 H5 . . 120.000000 ?
C6 C5 H5 . . 120.000000 ?
C1 C6 C5 . . 119.24(13) ?
C1 C6 C14 . . 120.76(12) ?
C5 C6 C14 . . 119.83(12) ?
N1 C7 C2 . . 112.10(11) ?
N1 C7 H7A . . 109.200000 ?
C2 C7 H7A . . 109.200000 ?
N1 C7 H7B . . 109.200000 ?
C2 C7 H7B . . 109.200000 ?
H7A C7 H7B . . 107.900000 ?
N1 C8A C9A . . 113.53(13) ?
N1 C8A C10A . . 116.52(15) ?
C9A C8A C10A . . 109.81(14) ?
N1 C8A H8A . . 105.300000 ?
C9A C8A H8A . . 105.300000 ?
C10A C8A H8A . . 105.300000 ?
C8A C9A H9AA . . 109.500000 ?
C8A C9A H9AB . . 109.500000 ?
H9AA C9A H9AB . . 109.500000 ?
C8A C9A H9AC . . 109.500000 ?
H9AA C9A H9AC . . 109.500000 ?
H9AB C9A H9AC . . 109.500000 ?
C8A C10A H10A . . 109.500000 ?
C8A C10A H10B . . 109.500000 ?
H10A C10A H10B . . 109.500000 ?
C8A C10A H10C . . 109.500000 ?
H10A C10A H10C . . 109.500000 ?
H10B C10A H10C . . 109.500000 ?
N1 C11A C12A . . 115.5(7) ?
N1 C11A C13A . . 113.8(4) ?
C12A C11A C13A . . 109.3(5) ?
N1 C11A H11A . . 105.800000 ?
C12A C11A H11A . . 105.800000 ?
C13A C11A H11A . . 105.800000 ?
C11A C12A H12A . . 109.500000 ?
C11A C12A H12B . . 109.500000 ?
H12A C12A H12B . . 109.500000 ?
C11A C12A H12C . . 109.500000 ?
H12A C12A H12C . . 109.500000 ?
H12B C12A H12C . . 109.500000 ?
C11A C13A H13A . . 109.500000 ?
C11A C13A H13B . . 109.500000 ?
H13A C13A H13B . . 109.500000 ?
C11A C13A H13C . . 109.500000 ?
H13A C13A H13C . . 109.500000 ?
H13B C13A H13C . . 109.500000 ?
N1 C8B C10B . . 104.8(12) ?
N1 C8B C9B . . 119.3(14) ?
C10B C8B C9B . . 107.8(13) ?
N1 C8B H8B . . 108.100000 ?
C10B C8B H8B . . 108.100000 ?
C9B C8B H8B . . 108.100000 ?
C8B C9B H9BA . . 109.500000 ?
C8B C9B H9BB . . 109.500000 ?
H9BA C9B H9BB . . 109.500000 ?
C8B C9B H9BC . . 109.500000 ?
H9BA C9B H9BC . . 109.500000 ?
H9BB C9B H9BC . . 109.500000 ?
C8B C10B H10D . . 109.500000 ?
C8B C10B H10E . . 109.500000 ?
H10D C10B H10E . . 109.500000 ?
C8B C10B H10F . . 109.500000 ?
H10D C10B H10F . . 109.500000 ?
H10E C10B H10F . . 109.500000 ?
C13B C11B C12B . . 109.2(14) ?
C13B C11B N1 . . 121.3(13) ?
C12B C11B N1 . . 115.(3) ?
C13B C11B H11B . . 103.000000 ?
C12B C11B H11B . . 103.000000 ?
N1 C11B H11B . . 103.000000 ?
C11B C12B H12D . . 109.500000 ?
C11B C12B H12E . . 109.500000 ?
H12D C12B H12E . . 109.500000 ?
C11B C12B H12F . . 109.500000 ?
H12D C12B H12F . . 109.500000 ?
H12E C12B H12F . . 109.500000 ?
C11B C13B H13D . . 109.500000 ?
C11B C13B H13E . . 109.500000 ?
H13D C13B H13E . . 109.500000 ?
C11B C13B H13F . . 109.500000 ?
H13D C13B H13F . . 109.500000 ?
H13E C13B H13F . . 109.500000 ?
N2 C14 C6 . . 113.30(11) ?
N2 C14 H14A . . 108.900000 ?
C6 C14 H14A . . 108.900000 ?
N2 C14 H14B . . 108.900000 ?
C6 C14 H14B . . 108.900000 ?
H14A C14 H14B . . 107.700000 ?
N2 C15 C17 . . 113.04(12) ?
N2 C15 C16 . . 113.44(11) ?
C17 C15 C16 . . 109.40(12) ?
N2 C15 H15 . . 106.800000 ?
C17 C15 H15 . . 106.800000 ?
C16 C15 H15 . . 106.800000 ?
C15 C16 H16A . . 109.500000 ?
C15 C16 H16B . . 109.500000 ?
H16A C16 H16B . . 109.500000 ?
C15 C16 H16C . . 109.500000 ?
H16A C16 H16C . . 109.500000 ?
H16B C16 H16C . . 109.500000 ?
C15 C17 H17A . . 109.500000 ?
C15 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
C15 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
N2 C18 C19 . . 111.49(11) ?
N2 C18 C20 . . 112.25(11) ?
C19 C18 C20 . . 110.40(12) ?
N2 C18 H18 . . 107.500000 ?
C19 C18 H18 . . 107.500000 ?
C20 C18 H18 . . 107.500000 ?
C18 C19 H19A . . 109.500000 ?
C18 C19 H19B . . 109.500000 ?
H19A C19 H19B . . 109.500000 ?
C18 C19 H19C . . 109.500000 ?
H19A C19 H19C . . 109.500000 ?
H19B C19 H19C . . 109.500000 ?
C18 C20 H20A . . 109.500000 ?
C18 C20 H20B . . 109.500000 ?
H20A C20 H20B . . 109.500000 ?
C18 C20 H20C . . 109.500000 ?
H20A C20 H20C . . 109.500000 ?
H20B C20 H20C . . 109.500000 ?
C26 C21 C22 . . 117.82(12) ?
C26 C21 Sb1 . . 124.74(10) ?
C22 C21 Sb1 . . 115.65(10) ?
C23 C22 C21 . . 122.76(13) ?
C23 C22 H22 . . 118.600000 ?
C21 C22 H22 . . 118.600000 ?
C22 C23 C24 . . 119.36(12) ?
C22 C23 C27 . . 120.93(13) ?
C24 C23 C27 . . 119.56(12) ?
O1 C24 C23 . . 121.40(13) ?
O1 C24 C25 . . 121.31(13) ?
C23 C24 C25 . . 117.28(12) ?
C26 C25 C24 . . 119.71(12) ?
C26 C25 C31 . . 120.74(12) ?
C24 C25 C31 . . 119.55(12) ?
C25 C26 C21 . . 122.67(12) ?
C25 C26 H26 . . 118.700000 ?
C21 C26 H26 . . 118.700000 ?
C30 C27 C29 . . 107.67(13) ?
C30 C27 C23 . . 112.28(12) ?
C29 C27 C23 . . 108.40(12) ?
C30 C27 C28 . . 106.81(13) ?
C29 C27 C28 . . 108.89(13) ?
C23 C27 C28 . . 112.64(12) ?
C27 C28 H28A . . 109.500000 ?
C27 C28 H28B . . 109.500000 ?
H28A C28 H28B . . 109.500000 ?
C27 C28 H28C . . 109.500000 ?
H28A C28 H28C . . 109.500000 ?
H28B C28 H28C . . 109.500000 ?
C27 C29 H29A . . 109.500000 ?
C27 C29 H29B . . 109.500000 ?
H29A C29 H29B . . 109.500000 ?
C27 C29 H29C . . 109.500000 ?
H29A C29 H29C . . 109.500000 ?
H29B C29 H29C . . 109.500000 ?
C27 C30 H30A . . 109.500000 ?
C27 C30 H30B . . 109.500000 ?
H30A C30 H30B . . 109.500000 ?
C27 C30 H30C . . 109.500000 ?
H30A C30 H30C . . 109.500000 ?
H30B C30 H30C . . 109.500000 ?
C34 C31 C33 . . 107.14(12) ?
C34 C31 C25 . . 112.29(12) ?
C33 C31 C25 . . 110.12(12) ?
C34 C31 C32 . . 107.17(12) ?
C33 C31 C32 . . 109.55(12) ?
C25 C31 C32 . . 110.45(11) ?
C31 C32 H32A . . 109.500000 ?
C31 C32 H32B . . 109.500000 ?
H32A C32 H32B . . 109.500000 ?
C31 C32 H32C . . 109.500000 ?
H32A C32 H32C . . 109.500000 ?
H32B C32 H32C . . 109.500000 ?
C31 C33 H33A . . 109.500000 ?
C31 C33 H33B . . 109.500000 ?
H33A C33 H33B . . 109.500000 ?
C31 C33 H33C . . 109.500000 ?
H33A C33 H33C . . 109.500000 ?
H33B C33 H33C . . 109.500000 ?
C31 C34 H34A . . 109.500000 ?
C31 C34 H34B . . 109.500000 ?
H34A C34 H34B . . 109.500000 ?
C31 C34 H34C . . 109.500000 ?
H34A C34 H34C . . 109.500000 ?
H34B C34 H34C . . 109.500000 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Sb1 C21 . 2.0882(13) ?
Sb1 C1 . 2.1219(13) ?
Sb1 N1 . 2.5472(11) ?
Sb1 N2 . 2.5667(11) ?
O1 C24 . 1.2688(17) ?
N1 C7 . 1.4845(17) ?
N1 C8B . 1.488(14) ?
N1 C11A . 1.502(5) ?
N1 C8A . 1.514(2) ?
N1 C11B . 1.540(14) ?
N2 C14 . 1.4901(17) ?
N2 C18 . 1.5124(17) ?
N2 C15 . 1.5155(17) ?
C1 C6 . 1.3891(19) ?
C1 C2 . 1.3975(19) ?
C2 C3 . 1.3893(19) ?
C2 C7 . 1.5068(19) ?
C3 C4 . 1.392(2) ?
C3 H3 . 0.950000 ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.950000 ?
C5 C6 . 1.3997(19) ?
C5 H5 . 0.950000 ?
C6 C14 . 1.5127(19) ?
C7 H7A . 0.990000 ?
C7 H7B . 0.990000 ?
C8A C9A . 1.520(2) ?
C8A C10A . 1.530(2) ?
C8A H8A . 1.000000 ?
C9A H9AA . 0.980000 ?
C9A H9AB . 0.980000 ?
C9A H9AC . 0.980000 ?
C10A H10A . 0.980000 ?
C10A H10B . 0.980000 ?
C10A H10C . 0.980000 ?
C11A C12A . 1.517(5) ?
C11A C13A . 1.541(5) ?
C11A H11A . 1.000000 ?
C12A H12A . 0.980000 ?
C12A H12B . 0.980000 ?
C12A H12C . 0.980000 ?
C13A H13A . 0.980000 ?
C13A H13B . 0.980000 ?
C13A H13C . 0.980000 ?
C8B C10B . 1.513(14) ?
C8B C9B . 1.525(14) ?
C8B H8B . 1.000000 ?
C9B H9BA . 0.980000 ?
C9B H9BB . 0.980000 ?
C9B H9BC . 0.980000 ?
C10B H10D . 0.980000 ?
C10B H10E . 0.980000 ?
C10B H10F . 0.980000 ?
C11B C13B . 1.520(13) ?
C11B C12B . 1.529(14) ?
C11B H11B . 1.000000 ?
C12B H12D . 0.980000 ?
C12B H12E . 0.980000 ?
C12B H12F . 0.980000 ?
C13B H13D . 0.980000 ?
C13B H13E . 0.980000 ?
C13B H13F . 0.980000 ?
C14 H14A . 0.990000 ?
C14 H14B . 0.990000 ?
C15 C17 . 1.528(2) ?
C15 C16 . 1.5321(19) ?
C15 H15 . 1.000000 ?
C16 H16A . 0.980000 ?
C16 H16B . 0.980000 ?
C16 H16C . 0.980000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 C19 . 1.521(2) ?
C18 C20 . 1.523(2) ?
C18 H18 . 1.000000 ?
C19 H19A . 0.980000 ?
C19 H19B . 0.980000 ?
C19 H19C . 0.980000 ?
C20 H20A . 0.980000 ?
C20 H20B . 0.980000 ?
C20 H20C . 0.980000 ?
C21 C26 . 1.4043(18) ?
C21 C22 . 1.4095(18) ?
C22 C23 . 1.3812(19) ?
C22 H22 . 0.950000 ?
C23 C24 . 1.456(2) ?
C23 C27 . 1.5387(18) ?
C24 C25 . 1.4598(19) ?
C25 C26 . 1.3785(19) ?
C25 C31 . 1.5354(19) ?
C26 H26 . 0.950000 ?
C27 C30 . 1.531(2) ?
C27 C29 . 1.538(2) ?
C27 C28 . 1.539(2) ?
C28 H28A . 0.980000 ?
C28 H28B . 0.980000 ?
C28 H28C . 0.980000 ?
C29 H29A . 0.980000 ?
C29 H29B . 0.980000 ?
C29 H29C . 0.980000 ?
C30 H30A . 0.980000 ?
C30 H30B . 0.980000 ?
C30 H30C . 0.980000 ?
C31 C34 . 1.531(2) ?
C31 C33 . 1.535(2) ?
C31 C32 . 1.538(2) ?
C32 H32A . 0.980000 ?
C32 H32B . 0.980000 ?
C32 H32C . 0.980000 ?
C33 H33A . 0.980000 ?
C33 H33B . 0.980000 ?
C33 H33C . 0.980000 ?
C34 H34A . 0.980000 ?
C34 H34B . 0.980000 ?
C34 H34C . 0.980000 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.3(2) ?
Sb1 C1 C2 C3 . . . . -179.87(10) ?
C6 C1 C2 C7 . . . . 179.43(12) ?
Sb1 C1 C2 C7 . . . . -1.76(17) ?
C1 C2 C3 C4 . . . . 0.5(2) ?
C7 C2 C3 C4 . . . . -177.52(14) ?
C2 C3 C4 C5 . . . . -1.7(2) ?
C3 C4 C5 C6 . . . . 0.9(2) ?
C2 C1 C6 C5 . . . . -2.1(2) ?
Sb1 C1 C6 C5 . . . . 179.18(10) ?
C2 C1 C6 C14 . . . . 173.11(13) ?
Sb1 C1 C6 C14 . . . . -5.66(18) ?
C4 C5 C6 C1 . . . . 0.9(2) ?
C4 C5 C6 C14 . . . . -174.27(14) ?
C8B N1 C7 C2 . . . . -179.8(8) ?
C11A N1 C7 C2 . . . . 71.4(3) ?
C8A N1 C7 C2 . . . . -155.78(12) ?
C11B N1 C7 C2 . . . . 62.5(10) ?
Sb1 N1 C7 C2 . . . . -41.27(12) ?
C3 C2 C7 N1 . . . . -147.35(13) ?
C1 C2 C7 N1 . . . . 34.58(17) ?
C7 N1 C8A C9A . . . . 174.22(13) ?
C11A N1 C8A C9A . . . . -58.0(3) ?
Sb1 N1 C8A C9A . . . . 65.92(15) ?
C7 N1 C8A C10A . . . . -56.69(19) ?
C11A N1 C8A C10A . . . . 71.1(3) ?
Sb1 N1 C8A C10A . . . . -165.00(14) ?
C7 N1 C11A C12A . . . . -162.6(7) ?
C8A N1 C11A C12A . . . . 70.6(8) ?
Sb1 N1 C11A C12A . . . . -54.4(8) ?
C7 N1 C11A C13A . . . . 69.8(5) ?
C8A N1 C11A C13A . . . . -57.0(5) ?
Sb1 N1 C11A C13A . . . . 178.0(4) ?
C7 N1 C8B C10B . . . . 50.7(14) ?
C11B N1 C8B C10B . . . . 170.0(12) ?
Sb1 N1 C8B C10B . . . . -75.3(14) ?
C7 N1 C8B C9B . . . . -70.0(16) ?
C11B N1 C8B C9B . . . . 49.2(18) ?
Sb1 N1 C8B C9B . . . . 163.9(12) ?
C7 N1 C11B C13B . . . . 47.(2) ?
C8B N1 C11B C13B . . . . -77.(2) ?
Sb1 N1 C11B C13B . . . . 151.0(18) ?
C7 N1 C11B C12B . . . . -178.(2) ?
C8B N1 C11B C12B . . . . 58.(2) ?
Sb1 N1 C11B C12B . . . . -74.(2) ?
C18 N2 C14 C6 . . . . 103.97(13) ?
C15 N2 C14 C6 . . . . -133.56(12) ?
Sb1 N2 C14 C6 . . . . -20.34(13) ?
C1 C6 C14 N2 . . . . 19.51(18) ?
C5 C6 C14 N2 . . . . -165.36(12) ?
C14 N2 C15 C17 . . . . 56.06(15) ?
C18 N2 C15 C17 . . . . 178.65(12) ?
Sb1 N2 C15 C17 . . . . -58.28(12) ?
C14 N2 C15 C16 . . . . -69.24(15) ?
C18 N2 C15 C16 . . . . 53.35(15) ?
Sb1 N2 C15 C16 . . . . 176.42(10) ?
C14 N2 C18 C19 . . . . -178.03(11) ?
C15 N2 C18 C19 . . . . 59.32(14) ?
Sb1 N2 C18 C19 . . . . -58.14(12) ?
C14 N2 C18 C20 . . . . -53.56(15) ?
C15 N2 C18 C20 . . . . -176.21(11) ?
Sb1 N2 C18 C20 . . . . 66.32(13) ?
C26 C21 C22 C23 . . . . 0.2(2) ?
Sb1 C21 C22 C23 . . . . 165.76(11) ?
C21 C22 C23 C24 . . . . 5.1(2) ?
C21 C22 C23 C27 . . . . -170.53(12) ?
C22 C23 C24 O1 . . . . 173.70(14) ?
C27 C23 C24 O1 . . . . -10.6(2) ?
C22 C23 C24 C25 . . . . -7.29(19) ?
C27 C23 C24 C25 . . . . 168.40(12) ?
O1 C24 C25 C26 . . . . -176.56(13) ?
C23 C24 C25 C26 . . . . 4.43(19) ?
O1 C24 C25 C31 . . . . 4.2(2) ?
C23 C24 C25 C31 . . . . -174.85(12) ?
C24 C25 C26 C21 . . . . 0.9(2) ?
C31 C25 C26 C21 . . . . -179.88(12) ?
C22 C21 C26 C25 . . . . -3.3(2) ?
Sb1 C21 C26 C25 . . . . -167.40(10) ?
C22 C23 C27 C30 . . . . -2.01(19) ?
C24 C23 C27 C30 . . . . -177.63(13) ?
C22 C23 C27 C29 . . . . 116.80(15) ?
C24 C23 C27 C29 . . . . -58.81(17) ?
C22 C23 C27 C28 . . . . -122.65(15) ?
C24 C23 C27 C28 . . . . 61.74(18) ?
C26 C25 C31 C34 . . . . -1.73(18) ?
C24 C25 C31 C34 . . . . 177.54(13) ?
C26 C25 C31 C33 . . . . -121.04(14) ?
C24 C25 C31 C33 . . . . 58.23(17) ?
C26 C25 C31 C32 . . . . 117.83(14) ?
C24 C25 C31 C32 . . . . -62.90(16) ?
