#------------------------------------------------------------------------------
#$Date: 2023-07-04 04:12:21 +0300 (Tue, 04 Jul 2023) $
#$Revision: 284768 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131817.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_7131817
loop_
_publ_author_name
'Weinert, Hanns M.'
'Schulte, Yannick'
'Gehlhaar, Alexander'
'Wölper, Christoph'
'Haberhauer, Gebhard'
'Schulz, Stephan'
_publ_section_title
;
 Metal-coordinated distibene and dibismuthene dications - isoelectronic
 analogues of butadiene dications.
;
_journal_issue                   50
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7755
_journal_page_last               7758
_journal_paper_doi               10.1039/d3cc01844j
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C30 H42 F3 Ga N2 O3 S'
_chemical_formula_weight         637.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_audit_update_record
;
2023-01-19 deposited with the CCDC.	2023-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.4691(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.9025(4)
_cell_length_b                   19.9339(9)
_cell_length_c                   9.8991(5)
_cell_measurement_reflns_used    9240
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.43
_cell_measurement_theta_min      2.52
_cell_volume                     1572.56(13)
_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 1.000
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0110
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            57529
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.581
_diffrn_reflns_theta_min         2.043
_exptl_absorpt_coefficient_mu    0.991
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 SADABS
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       block
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.182
_refine_diff_density_max         2.838
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         6296
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0305
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0450P)²+0.7876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0858
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5891
_reflns_number_total             6296
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc01844j2.cif
_cod_data_source_block           mw_117_1film
_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 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               7131817
_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   0.752
_shelx_estimated_absorpt_t_max   0.840
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
Ga1 Ga 0.47836(2) 0.250000 0.21867(2) 0.01215(5) Uani 1 2 d S T P A .
H1 H 0.300(3) 0.250000 0.057(3) 0.015 Uiso 1 2 d S U P . .
O1 O 0.65613(17) 0.250000 0.15840(13) 0.0291(3) Uani 1 2 d DS T P . .
C1 C 0.50596(12) 0.31312(5) 0.48304(10) 0.01382(15) Uani 1 1 d . . . . .
N1 N 0.52912(10) 0.32209(4) 0.35934(9) 0.01260(13) Uani 1 1 d . . . . .
C2 C 0.48177(17) 0.250000 0.53281(15) 0.0151(2) Uani 1 2 d S T P . .
H2 H 0.444661 0.250000 0.609138 0.018 Uiso 1 2 calc R U P . .
C4 C 0.57432(13) 0.38702(5) 0.32425(11) 0.01443(16) Uani 1 1 d . . . . .
C3 C 0.50514(15) 0.37313(6) 0.57492(12) 0.0215(2) Uani 1 1 d . . . . .
H3A H 0.600802 0.402112 0.591729 0.032 Uiso 1 1 calc R U . . .
H3B H 0.513537 0.358130 0.672317 0.032 Uiso 1 1 calc R U . . .
H3C H 0.400542 0.398232 0.520538 0.032 Uiso 1 1 calc R U . . .
C5 C 0.74555(13) 0.40108(5) 0.37178(12) 0.01725(17) Uani 1 1 d . . . . .
C7 C 0.66367(17) 0.50967(6) 0.24887(14) 0.0237(2) Uani 1 1 d . . . . .
H7 H 0.694441 0.551850 0.224037 0.028 Uiso 1 1 calc R U . . .
C6 C 0.78725(15) 0.46364(6) 0.33380(14) 0.0222(2) Uani 1 1 d . . . . .
H6 H 0.901942 0.474864 0.366610 0.027 Uiso 1 1 calc R U . . .
C9 C 0.44749(13) 0.43290(5) 0.23815(11) 0.01681(17) Uani 1 1 d . . . . .
C8 C 0.49608(16) 0.49419(6) 0.20045(13) 0.0216(2) Uani 1 1 d . . . . .
H8 H 0.412615 0.525610 0.140688 0.026 Uiso 1 1 calc R U . . .
C10 C 0.88111(14) 0.35029(5) 0.46165(13) 0.02097(19) Uani 1 1 d . . . . .
H10 H 0.831165 0.304530 0.431867 0.025 Uiso 1 1 calc R U . . .
C11 C 0.94011(17) 0.35773(8) 0.63183(15) 0.0311(3) Uani 1 1 d . . . . .
H11A H 0.979451 0.403703 0.662721 0.047 Uiso 1 1 calc R U . . .
H11B H 1.032014 0.326228 0.686023 0.047 Uiso 1 1 calc R U . . .
H11C H 0.846601 0.348030 0.655601 0.047 Uiso 1 1 calc R U . . .
C12 C 1.03310(19) 0.35416(8) 0.42840(18) 0.0332(3) Uani 1 1 d . . . . .
H12A H 0.994996 0.353575 0.319006 0.050 Uiso 1 1 calc R U . . .
H12B H 1.106680 0.315619 0.474270 0.050 Uiso 1 1 calc R U . . .
H12C H 1.094940 0.395762 0.470623 0.050 Uiso 1 1 calc R U . . .
C13 C 0.26273(14) 0.41778(6) 0.18446(12) 0.02035(19) Uani 1 1 d . . . . .
H13 H 0.253322 0.375494 0.234511 0.024 Uiso 1 1 calc R U . . .
C14 C 0.17399(17) 0.47400(7) 0.22731(17) 0.0292(2) Uani 1 1 d . . . . .
H14A H 0.178770 0.515677 0.176859 0.044 Uiso 1 1 calc R U . . .
H14B H 0.230020 0.480630 0.336874 0.044 Uiso 1 1 calc R U . . .
H14C H 0.056540 0.461564 0.195528 0.044 Uiso 1 1 calc R U . . .
C15 C 0.17546(17) 0.40651(8) 0.01311(15) 0.0314(3) Uani 1 1 d . . . . .
H15A H 0.177849 0.448182 -0.038413 0.047 Uiso 1 1 calc R U . . .
H15B H 0.058758 0.393027 -0.018268 0.047 Uiso 1 1 calc R U . . .
H15C H 0.234058 0.371119 -0.013368 0.047 Uiso 1 1 calc R U . . .
S1 S 0.64346(10) 0.22459(4) 0.00703(7) 0.03740(17) Uani 0.5 1 d . . P A -1
F1 F 0.9558(2) 0.2614(4) 0.1165(2) 0.0492(16) Uani 0.5 1 d . . P A -1
C16 C 0.8105(4) 0.27606(18) 0.0046(3) 0.0359(6) Uani 0.5 1 d . . P A -1
F3 F 0.7810(5) 0.34082(17) 0.0159(4) 0.0623(8) Uani 0.5 1 d . . P A -1
O3 O 0.6953(7) 0.1577(2) 0.0021(6) 0.0799(17) Uani 0.5 1 d D . P A -1
F2 F 0.8190(3) 0.2665(2) -0.1246(2) 0.0628(16) Uani 0.5 1 d . . P A -1
O2 O 0.4945(3) 0.2550(9) -0.1129(2) 0.080(2) Uani 0.5 1 d D . P A -1
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'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 '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'
H H 0.0000 0.0000 '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
N1 Ga1 N1 97.60(5) 4_565 . ?
N1 Ga1 O1 105.43(4) 4_565 . ?
N1 Ga1 O1 105.43(4) . . ?
S1 O1 Ga1 126.09(8) . . ?
N1 C1 C2 123.40(9) . . ?
N1 C1 C3 119.34(9) . . ?
C2 C1 C3 117.26(9) . . ?
C1 N1 C4 120.81(8) . . ?
C1 N1 Ga1 118.86(7) . . ?
C4 N1 Ga1 120.00(6) . . ?
C1 C2 C1 127.58(12) 4_565 . ?
C9 C4 C5 121.99(9) . . ?
C9 C4 N1 119.62(9) . . ?
C5 C4 N1 118.32(9) . . ?
C6 C5 C4 117.69(10) . . ?
C6 C5 C10 120.91(10) . . ?
C4 C5 C10 121.40(9) . . ?
C8 C7 C6 120.18(10) . . ?
C7 C6 C5 121.14(11) . . ?
C8 C9 C4 117.93(10) . . ?
C8 C9 C13 119.70(9) . . ?
C4 C9 C13 122.36(9) . . ?
C7 C8 C9 121.04(10) . . ?
C5 C10 C12 112.80(10) . . ?
C5 C10 C11 111.86(10) . . ?
C12 C10 C11 109.21(10) . . ?
C9 C13 C15 110.61(10) . . ?
C9 C13 C14 111.67(10) . . ?
C15 C13 C14 110.04(10) . . ?
O3 S1 O2 123.6(6) . . ?
O3 S1 O1 117.4(2) . . ?
O2 S1 O1 107.5(4) . . ?
O3 S1 C16 104.5(2) . . ?
O2 S1 C16 101.9(5) . . ?
O1 S1 C16 97.00(11) . . ?
F1 C16 F2 108.9(3) . . ?
F1 C16 F3 107.6(4) . . ?
F2 C16 F3 108.5(3) . . ?
F1 C16 S1 111.7(3) . . ?
F2 C16 S1 109.3(2) . . ?
F3 C16 S1 110.7(2) . . ?
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
Ga1 N1 1.9099(8) 4_565 ?
Ga1 N1 1.9099(8) . ?
Ga1 O1 1.9241(12) . ?
O1 S1 1.5375(12) . ?
C1 N1 1.3412(12) . ?
C1 C2 1.4025(12) . ?
C1 C3 1.5047(14) . ?
N1 C4 1.4431(13) . ?
C4 C9 1.4071(14) . ?
C4 C5 1.4086(14) . ?
C5 C6 1.3995(15) . ?
C5 C10 1.5217(15) . ?
C7 C8 1.3833(18) . ?
C7 C6 1.3909(17) . ?
C9 C8 1.4010(15) . ?
C9 C13 1.5164(16) . ?
C10 C12 1.5304(19) . ?
C10 C11 1.5320(18) . ?
C13 C15 1.5350(17) . ?
C13 C14 1.5358(17) . ?
S1 O3 1.419(5) . ?
S1 O2 1.460(7) . ?
S1 C16 1.815(3) . ?
F1 C16 1.307(4) . ?
C16 F2 1.329(3) . ?
C16 F3 1.332(5) . ?
