#------------------------------------------------------------------------------
#$Date: 2022-03-04 01:12:45 +0200 (Fri, 04 Mar 2022) $
#$Revision: 273286 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/65/1566524.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_1566524
loop_
_publ_author_name
'Weinert, Hanns Micha'
'Wölper, Christoph'
'Schulz, Stephan'
_publ_section_title
;
 Synthesis of Distibiranes and Azadistibiranes by Cycloaddition Reactions
 of Distibenes with Diazomethanes and Azides
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00314G
_journal_year                    2022
_chemical_formula_sum            'C74 H104 Ga2 N8 Sb2'
_chemical_formula_weight         1488.59
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2021-12-16 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                93.2189(14)
_cell_angle_beta                 97.3354(14)
_cell_angle_gamma                107.9954(14)
_cell_formula_units_Z            1
_cell_length_a                   10.4552(4)
_cell_length_b                   11.9732(4)
_cell_length_c                   14.9227(5)
_cell_measurement_reflns_used    9032
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.50
_cell_measurement_theta_min      2.59
_cell_volume                     1753.06(11)
_computing_cell_refinement       'BRUKER APEX3(v2019.1-0)'
_computing_data_collection       'BRUKER APEX3(v2019.1-0)'
_computing_data_reduction        'BRUKER APEX3(v2019.1-0)'
_computing_molecular_graphics    'ORTEP/PLATON (Spek)'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'BRUKER APEX3(v2019.1-0)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker D8 KAPPA II (APEX II detector)'
_diffrn_measurement_method       'Data collection strategy APEX 3/QUEEN'
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0093
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            139632
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.595
_diffrn_reflns_theta_min         2.072
_exptl_absorpt_coefficient_mu    1.569
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            'dark brown'
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.116
_refine_diff_density_max         0.928
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     400
_refine_ls_number_reflns         13767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0191
_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)+(0.0281P)²+0.8077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0525
_refine_ls_wR_factor_ref         0.0543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12730
_reflns_number_total             13767
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2sc00314g2.cif
_cod_data_source_block           mw_150_2m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_secondary' value 'diffmap' was
changed to 'difmap'.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1566524
_shelx_shelxl_version_number     2017/1
_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_min   0.761
_shelx_estimated_absorpt_t_max   0.839
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
Sb1 Sb 0.45917(2) 0.55436(2) 0.43167(2) 0.01463(2) Uani 1 1 d . . . . .
Ga1 Ga 0.33321(2) 0.39024(2) 0.23686(2) 0.00849(2) Uani 1 1 d . . . . .
N1 N 0.19100(8) 0.26444(7) 0.15631(5) 0.01057(12) Uani 1 1 d . . . . .
N2 N 0.28528(8) 0.52056(7) 0.18058(5) 0.01067(12) Uani 1 1 d . . . . .
N3 N 0.50272(8) 0.39014(8) 0.21293(6) 0.01463(14) Uani 1 1 d . . . . .
N4 N 0.31745(8) 0.40381(7) 0.36092(5) 0.01225(13) Uani 1 1 d . . . . .
C1 C 0.15305(9) 0.28435(8) 0.07135(6) 0.01198(14) Uani 1 1 d . . . . .
C2 C 0.17986(10) 0.39732(9) 0.04124(6) 0.01388(15) Uani 1 1 d . . . . .
H2 H 0.160977 0.399637 -0.022486 0.017 Uiso 1 1 calc R U . . .
C3 C 0.23108(9) 0.50707(8) 0.09369(6) 0.01158(14) Uani 1 1 d . . . . .
C4 C 0.07356(11) 0.18246(9) 0.00161(7) 0.01715(17) Uani 1 1 d . . . . .
H4A H 0.017390 0.209394 -0.044467 0.026 Uiso 1 1 calc R U . . .
H4B H 0.014877 0.119699 0.031360 0.026 Uiso 1 1 calc R U . . .
H4C H 0.136733 0.152045 -0.027415 0.026 Uiso 1 1 calc R U . . .
C5 C 0.22013(11) 0.61303(9) 0.04618(7) 0.01753(17) Uani 1 1 d . . . . .
H5A H 0.302157 0.646419 0.018665 0.026 Uiso 1 1 calc R U . . .
H5B H 0.211012 0.672718 0.090396 0.026 Uiso 1 1 calc R U . . .
H5C H 0.140141 0.588495 -0.001253 0.026 Uiso 1 1 calc R U . . .
C6 C 0.13954(9) 0.14733(8) 0.18466(6) 0.01164(14) Uani 1 1 d . . . . .
C7 C 0.20473(10) 0.06278(8) 0.16997(6) 0.01314(15) Uani 1 1 d . . . . .
C8 C 0.15518(11) -0.04673(9) 0.20388(7) 0.01655(16) Uani 1 1 d . . . . .
H8 H 0.199164 -0.104337 0.195784 0.020 Uiso 1 1 calc R U . . .
C9 C 0.04349(11) -0.07241(9) 0.24886(8) 0.01928(18) Uani 1 1 d . . . . .
H9 H 0.010880 -0.147329 0.270945 0.023 Uiso 1 1 calc R U . . .
C10 C -0.02101(11) 0.01137(9) 0.26176(7) 0.01798(17) Uani 1 1 d . . . . .
H10 H -0.098590 -0.007522 0.291892 0.022 Uiso 1 1 calc R U . . .
C11 C 0.02586(9) 0.12271(9) 0.23133(7) 0.01371(15) Uani 1 1 d . . . . .
C12 C 0.32693(10) 0.08437(8) 0.12006(7) 0.01468(16) Uani 1 1 d . . . . .
H12 H 0.346481 0.164463 0.098102 0.018 Uiso 1 1 calc R U . . .
C13 C 0.29852(12) -0.00667(10) 0.03751(8) 0.02082(19) Uani 1 1 d . . . . .
H13A H 0.221389 -0.001468 -0.004931 0.031 Uiso 1 1 calc R U . . .
H13B H 0.276811 -0.086079 0.057507 0.031 Uiso 1 1 calc R U . . .
H13C H 0.379201 0.009340 0.007185 0.031 Uiso 1 1 calc R U . . .
C14 C 0.45327(11) 0.08153(11) 0.18270(8) 0.0218(2) Uani 1 1 d . . . . .
H14A H 0.438263 0.002087 0.201802 0.033 Uiso 1 1 calc R U . . .
H14B H 0.470756 0.138364 0.236278 0.033 Uiso 1 1 calc R U . . .
H14C H 0.531790 0.102333 0.150186 0.033 Uiso 1 1 calc R U . . .
C15 C -0.04313(10) 0.21494(9) 0.24905(7) 0.01605(16) Uani 1 1 d . . . . .
H15 H 0.030113 0.292621 0.266167 0.019 Uiso 1 1 calc R U . . .
C16 C -0.13489(12) 0.22752(12) 0.16426(8) 0.0245(2) Uani 1 1 d . . . . .
H16A H -0.079988 0.252954 0.116110 0.037 Uiso 1 1 calc R U . . .
H16B H -0.178672 0.286338 0.178873 0.037 Uiso 1 1 calc R U . . .
H16C H -0.204750 0.151321 0.143527 0.037 Uiso 1 1 calc R U . . .
C17 C -0.12659(12) 0.19109(12) 0.32739(8) 0.0229(2) Uani 1 1 d . . . . .
H17A H -0.153903 0.260132 0.343002 0.034 Uiso 1 1 calc R U . . .
H17B H -0.071283 0.175655 0.380418 0.034 Uiso 1 1 calc R U . . .
H17C H -0.207911 0.122240 0.308784 0.034 Uiso 1 1 calc R U . . .
C18 C 0.32281(9) 0.63314(8) 0.23396(6) 0.01175(14) Uani 1 1 d . . . . .
C19 C 0.45074(10) 0.71751(8) 0.23354(7) 0.01368(15) Uani 1 1 d . . . . .
C20 C 0.48878(11) 0.81960(9) 0.29382(7) 0.01812(17) Uani 1 1 d . . . . .
H20 H 0.575183 0.877227 0.294852 0.022 Uiso 1 1 calc R U . . .
C21 C 0.40289(12) 0.83852(10) 0.35223(8) 0.02100(19) Uani 1 1 d . . . . .
H21 H 0.431217 0.907957 0.393533 0.025 Uiso 1 1 calc R U . . .
C22 C 0.27542(12) 0.75593(10) 0.35034(7) 0.01930(18) Uani 1 1 d . . . . .
H22 H 0.216081 0.770577 0.389344 0.023 Uiso 1 1 calc R U . . .
C23 C 0.23311(10) 0.65177(9) 0.29205(7) 0.01433(15) Uani 1 1 d . . . . .
C24 C 0.54959(10) 0.70151(9) 0.17180(7) 0.01599(16) Uani 1 1 d . . . . .
H24 H 0.505851 0.625083 0.132724 0.019 Uiso 1 1 calc R U . . .
C25 C 0.58255(13) 0.80120(11) 0.10966(8) 0.0239(2) Uani 1 1 d . . . . .
H25A H 0.638387 0.784364 0.066034 0.036 Uiso 1 1 calc R U . . .
H25B H 0.632585 0.876100 0.146426 0.036 Uiso 1 1 calc R U . . .
H25C H 0.497723 0.806808 0.076849 0.036 Uiso 1 1 calc R U . . .
C26 C 0.68136(11) 0.69630(11) 0.22661(9) 0.0224(2) Uani 1 1 d . . . . .
H26A H 0.741800 0.683165 0.184993 0.034 Uiso 1 1 calc R U . . .
H26B H 0.660163 0.631397 0.265162 0.034 Uiso 1 1 calc R U . . .
H26C H 0.726492 0.771009 0.264768 0.034 Uiso 1 1 calc R U . . .
C27 C 0.09476(11) 0.55998(9) 0.29133(8) 0.01795(17) Uani 1 1 d . . . . .
H27 H 0.105973 0.480659 0.280062 0.022 Uiso 1 1 calc R U . . .
C28 C -0.00924(12) 0.57137(12) 0.21340(9) 0.0260(2) Uani 1 1 d . . . . .
H28A H 0.020455 0.557377 0.155311 0.039 Uiso 1 1 calc R U . . .
H28B H -0.016790 0.650944 0.219235 0.039 Uiso 1 1 calc R U . . .
H28C H -0.098022 0.513092 0.215717 0.039 Uiso 1 1 calc R U . . .
C29 C 0.04035(14) 0.56266(14) 0.38147(10) 0.0306(3) Uani 1 1 d . . . . .
H29A H 0.014618 0.634138 0.390187 0.046 Uiso 1 1 calc R U . . .
H29B H 0.111071 0.562657 0.431360 0.046 Uiso 1 1 calc R U . . .
H29C H -0.039520 0.492908 0.380669 0.046 Uiso 1 1 calc R U . . .
C30 C 0.53904(11) 0.39426(10) 0.12269(7) 0.01855(18) Uani 1 1 d . . . . .
H30A H 0.558214 0.321711 0.104903 0.028 Uiso 1 1 calc R U . . .
H30B H 0.620095 0.462493 0.122157 0.028 Uiso 1 1 calc R U . . .
H30C H 0.463441 0.401361 0.079776 0.028 Uiso 1 1 calc R U . . .
C31 C 0.61134(10) 0.38315(10) 0.28042(8) 0.01852(18) Uani 1 1 d . . . . .
H31A H 0.639787 0.315544 0.262426 0.028 Uiso 1 1 calc R U . . .
H31B H 0.579198 0.373291 0.339261 0.028 Uiso 1 1 calc R U . . .
H31C H 0.688728 0.455863 0.285350 0.028 Uiso 1 1 calc R U . . .
C32 C 0.27606(9) 0.30421(8) 0.40971(6) 0.01241(14) Uani 1 1 d . . . . .
C33 C 0.31629(11) 0.20532(9) 0.39502(7) 0.01702(17) Uani 1 1 d . . . . .
H33 H 0.375580 0.204829 0.351875 0.020 Uiso 1 1 calc R U . . .
C34 C 0.27131(14) 0.10618(10) 0.44248(8) 0.0245(2) Uani 1 1 d . . . . .
H34 H 0.298144 0.038715 0.429992 0.029 Uiso 1 1 calc R U . . .
C35 C 0.18792(14) 0.10624(11) 0.50749(8) 0.0264(2) Uani 1 1 d . . . . .
H35 H 0.157765 0.039488 0.540119 0.032 Uiso 1 1 calc R U . . .
C36 C 0.14910(12) 0.20542(11) 0.52420(8) 0.0235(2) Uani 1 1 d . . . . .
H36 H 0.092466 0.206502 0.569001 0.028 Uiso 1 1 calc R U . . .
C37 C 0.19190(11) 0.30316(10) 0.47632(7) 0.01796(17) Uani 1 1 d . . . . .
H37 H 0.164005 0.370067 0.488713 0.022 Uiso 1 1 calc R U . . .
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'
Ga Ga 0.2307 1.6083 '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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Sb1 Sb1 95.83(2) . 2_666 ?
N3 Ga1 N4 114.86(4) . . ?
N3 Ga1 N1 109.30(4) . . ?
N4 Ga1 N1 117.88(3) . . ?
N3 Ga1 N2 109.88(4) . . ?
N4 Ga1 N2 108.28(3) . . ?
N1 Ga1 N2 94.62(3) . . ?
C1 N1 C6 119.80(8) . . ?
C1 N1 Ga1 119.27(6) . . ?
C6 N1 Ga1 120.53(6) . . ?
C3 N2 C18 121.15(8) . . ?
C3 N2 Ga1 120.47(6) . . ?
C18 N2 Ga1 118.11(6) . . ?
C30 N3 C31 112.52(8) . . ?
C30 N3 Ga1 122.81(7) . . ?
C31 N3 Ga1 124.65(7) . . ?
C32 N4 Ga1 122.29(6) . . ?
C32 N4 Sb1 116.72(6) . . ?
Ga1 N4 Sb1 112.55(4) . . ?
N1 C1 C2 124.02(8) . . ?
N1 C1 C4 120.09(9) . . ?
C2 C1 C4 115.87(8) . . ?
C3 C2 C1 128.01(8) . . ?
N2 C3 C2 123.43(8) . . ?
N2 C3 C5 120.20(8) . . ?
C2 C3 C5 116.37(8) . . ?
C7 C6 C11 121.24(9) . . ?
C7 C6 N1 120.81(8) . . ?
C11 C6 N1 117.88(8) . . ?
C8 C7 C6 118.20(9) . . ?
C8 C7 C12 118.35(8) . . ?
C6 C7 C12 123.44(8) . . ?
C9 C8 C7 121.19(10) . . ?
C8 C9 C10 119.96(9) . . ?
C9 C10 C11 121.28(9) . . ?
C10 C11 C6 118.10(9) . . ?
C10 C11 C15 120.53(9) . . ?
C6 C11 C15 121.36(9) . . ?
C7 C12 C14 111.41(9) . . ?
C7 C12 C13 111.51(8) . . ?
C14 C12 C13 109.11(9) . . ?
C11 C15 C16 112.09(9) . . ?
C11 C15 C17 113.36(9) . . ?
C16 C15 C17 108.80(9) . . ?
C19 C18 C23 121.29(9) . . ?
C19 C18 N2 120.26(8) . . ?
C23 C18 N2 118.22(8) . . ?
C20 C19 C18 118.23(9) . . ?
C20 C19 C24 118.75(9) . . ?
C18 C19 C24 123.01(9) . . ?
C21 C20 C19 121.24(10) . . ?
C20 C21 C22 119.96(10) . . ?
C21 C22 C23 121.04(10) . . ?
C22 C23 C18 118.21(9) . . ?
C22 C23 C27 121.12(9) . . ?
C18 C23 C27 120.66(9) . . ?
C19 C24 C26 111.31(9) . . ?
C19 C24 C25 111.05(9) . . ?
C26 C24 C25 109.67(9) . . ?
C23 C27 C29 113.45(10) . . ?
C23 C27 C28 111.15(9) . . ?
C29 C27 C28 110.34(10) . . ?
C33 C32 C37 117.60(9) . . ?
C33 C32 N4 122.31(9) . . ?
C37 C32 N4 120.08(9) . . ?
C32 C33 C34 121.44(10) . . ?
C35 C34 C33 120.26(11) . . ?
C34 C35 C36 118.93(10) . . ?
C35 C36 C37 120.94(11) . . ?
C36 C37 C32 120.80(10) . . ?
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
Sb1 N4 2.0727(8) . ?
Sb1 Sb1 2.66878(14) 2_666 ?
Ga1 N3 1.8524(8) . ?
Ga1 N4 1.8818(8) . ?
Ga1 N1 1.9700(8) . ?
Ga1 N2 1.9785(8) . ?
N1 C1 1.3362(12) . ?
N1 C6 1.4468(12) . ?
N2 C3 1.3270(11) . ?
N2 C18 1.4416(12) . ?
N3 C30 1.4445(13) . ?
N3 C31 1.4447(13) . ?
N4 C32 1.4137(12) . ?
C1 C2 1.4057(13) . ?
C1 C4 1.5074(13) . ?
C2 C3 1.4031(13) . ?
C3 C5 1.5151(13) . ?
C6 C7 1.4061(13) . ?
C6 C11 1.4150(13) . ?
C7 C8 1.4019(13) . ?
C7 C12 1.5214(14) . ?
C8 C9 1.3822(15) . ?
C9 C10 1.3883(15) . ?
C10 C11 1.3945(14) . ?
C11 C15 1.5224(14) . ?
C12 C14 1.5282(15) . ?
C12 C13 1.5328(15) . ?
C15 C16 1.5313(16) . ?
C15 C17 1.5342(15) . ?
C18 C19 1.4062(13) . ?
C18 C23 1.4128(13) . ?
C19 C20 1.3951(14) . ?
C19 C24 1.5163(14) . ?
C20 C21 1.3860(16) . ?
C21 C22 1.3884(17) . ?
C22 C23 1.3952(14) . ?
C23 C27 1.5208(15) . ?
C24 C26 1.5303(16) . ?
C24 C25 1.5346(15) . ?
C27 C29 1.5283(16) . ?
C27 C28 1.5297(17) . ?
C32 C33 1.3889(14) . ?
C32 C37 1.4073(14) . ?
C33 C34 1.4023(15) . ?
C34 C35 1.3846(18) . ?
C35 C36 1.3884(19) . ?
C36 C37 1.3901(15) . ?
