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#$Date: 2019-11-24 05:55:29 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236873 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/76/4087610.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_4087610
loop_
_publ_author_name
'Novikov, Roman A.'
'Potapov, Konstantin V.'
'Chistikov, Daniil N.'
'Tarasova, Anna V.'
'Grigoriev, Michail S.'
'Timofeev, Vladimir P.'
'Tomilov, Yury V.'
_publ_section_title
;
 Synthesis and Structures of Cyclopropanedicarboxylate Gallium Complexes
;
_journal_issue                   17
_journal_name_full               Organometallics
_journal_page_first              4238
_journal_paper_doi               10.1021/acs.organomet.5b00399
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C14 H20 Br8 Ga4 O10, C H2 Cl2'
_chemical_formula_sum            'C15 H22 Br8 Cl2 Ga4 O10'
_chemical_formula_weight         1351.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 104.382(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.6176(13)
_cell_length_b                   13.6696(9)
_cell_length_c                   17.6101(14)
_cell_measurement_reflns_used    1844
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.85
_cell_volume                     3641.7(5)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT-Plus (Bruker, 1998)'
_computing_molecular_graphics    'SHELXTL97 (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       'ω- and φ-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  0.0642
_diffrn_reflns_av_unetI/netI     0.0773
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11362
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         4.193
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    11.892
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.465
_exptl_crystal_description       fragment
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         1.184
_refine_diff_density_min         -1.159
_refine_diff_density_rms         0.169
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         3183
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0423
_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)+(0.0281P)²+8.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0716
_refine_ls_wR_factor_ref         0.0822
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2142
_reflns_number_total             3183
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00399_si_006.cif
_cod_data_source_block           T82
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4087610
_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   0.100
_shelx_estimated_absorpt_t_max   0.200
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Ga1 Ga 0.5000 0.34438(7) 0.2500 0.0128(3) Uani 1 2 d S T P
Ga2 Ga 0.5000 0.55013(8) 0.2500 0.0194(3) Uani 1 2 d S T P
Ga3 Ga 0.31023(5) 0.45374(6) 0.14428(5) 0.0191(2) Uani 1 1 d . . .
Br1 Br 0.45916(6) 0.63510(7) 0.34726(5) 0.0472(3) Uani 1 1 d . . .
Br2 Br 0.32241(5) 0.38642(6) 0.02626(5) 0.0282(2) Uani 1 1 d . . .
Br3 Br 0.21223(5) 0.36577(5) 0.19695(5) 0.0301(2) Uani 1 1 d . . .
Br4 Br 0.26838(5) 0.61742(5) 0.13166(5) 0.0294(2) Uani 1 1 d . . .
Cl1 Cl 0.0000 0.4632(2) 0.2500 0.0447(8) Uani 1 2 d S T P
Cl2 Cl 0.1149(3) 0.3729(3) 0.3945(3) 0.0365(11) Uani 0.5 1 d . . P
O1 O 0.4212(3) 0.4490(3) 0.2101(3) 0.0150(11) Uani 1 1 d . . .
O2 O 0.4167(3) 0.2382(3) 0.2020(3) 0.0138(11) Uani 1 1 d . . .
O3 O 0.5502(3) 0.3329(3) 0.1576(3) 0.0152(11) Uani 1 1 d . . .
O4 O 0.3583(3) 0.1121(3) 0.1294(3) 0.0241(13) Uani 1 1 d . . .
O5 O 0.5781(3) 0.2810(3) 0.0477(3) 0.0248(13) Uani 1 1 d . . .
C1 C 0.4151(5) 0.1840(5) 0.1459(4) 0.0158(17) Uani 1 1 d . . .
C2 C 0.5362(5) 0.2736(5) 0.1031(4) 0.0159(17) Uani 1 1 d . . .
C3 C 0.2971(5) 0.0987(5) 0.1790(5) 0.028(2) Uani 1 1 d . . .
H3A H 0.2586 0.0427 0.1601 0.042 Uiso 1 1 calc R U .
H3B H 0.3306 0.0866 0.2331 0.042 Uiso 1 1 calc R U .
H3C H 0.2611 0.1577 0.1772 0.042 Uiso 1 1 calc R U .
C4 C 0.6414(6) 0.3602(5) 0.0534(5) 0.040(2) Uani 1 1 d . . .
H4A H 0.6680 0.3575 0.0086 0.059 Uiso 1 1 calc R U .
H4B H 0.6112 0.4230 0.0535 0.059 Uiso 1 1 calc R U .
H4C H 0.6878 0.3534 0.1022 0.059 Uiso 1 1 calc R U .
C5 C 0.4740(5) 0.1914(5) 0.0929(4) 0.0170(17) Uani 1 1 d . . .
C6 C 0.5078(6) 0.0939(5) 0.0645(5) 0.032(2) Uani 1 1 d . . .
H6A H 0.5681 0.0934 0.0560 0.038 Uiso 1 1 calc R U .
H6B H 0.4896 0.0319 0.0849 0.038 Uiso 1 1 calc R U .
C7 C 0.4395(6) 0.1504(6) 0.0091(5) 0.036(2) Uani 1 1 d . . .
H7A H 0.3788 0.1233 -0.0051 0.043 Uiso 1 1 calc R U .
H7B H 0.4572 0.1848 -0.0340 0.043 Uiso 1 1 calc R U .
C8 C 0.0407(12) 0.3547(11) 0.3025(10) 0.043(5) Uani 0.5 1 d . . P
H8A H -0.0103 0.3165 0.3102 0.051 Uiso 0.5 1 calc R U P
H8B H 0.0705 0.3148 0.2697 0.051 Uiso 0.5 1 calc R U P
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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
O1 Ga1 O1 82.6(3) 2_655 .
O1 Ga1 O3 96.20(18) 2_655 2_655
O1 Ga1 O3 90.65(18) . 2_655
O1 Ga1 O3 90.65(18) 2_655 .
O1 Ga1 O3 96.20(18) . .
O3 Ga1 O3 170.9(3) 2_655 .
O1 Ga1 O2 95.53(18) 2_655 2_655
O1 Ga1 O2 176.68(19) . 2_655
O3 Ga1 O2 86.80(18) 2_655 2_655
O3 Ga1 O2 86.56(17) . 2_655
O1 Ga1 O2 176.68(19) 2_655 .
O1 Ga1 O2 95.53(18) . .
O3 Ga1 O2 86.56(17) 2_655 .
O3 Ga1 O2 86.80(18) . .
O2 Ga1 O2 86.5(3) 2_655 .
O1 Ga1 Ga2 41.31(13) 2_655 .
O1 Ga1 Ga2 41.31(13) . .
O3 Ga1 Ga2 94.56(13) 2_655 .
O3 Ga1 Ga2 94.55(13) . .
O2 Ga1 Ga2 136.77(13) 2_655 .
O2 Ga1 Ga2 136.78(13) . .
O1 Ga2 O1 84.5(3) 2_655 .
O1 Ga2 Br1 112.17(13) 2_655 2_655
O1 Ga2 Br1 111.97(13) . 2_655
O1 Ga2 Br1 111.98(13) 2_655 .
O1 Ga2 Br1 112.17(13) . .
Br1 Ga2 Br1 118.96(7) 2_655 .
O1 Ga2 Ga1 42.27(13) 2_655 .
O1 Ga2 Ga1 42.27(13) . .
Br1 Ga2 Ga1 120.52(3) 2_655 .
Br1 Ga2 Ga1 120.52(3) . .
O1 Ga3 Br3 110.13(13) . .
O1 Ga3 Br2 106.09(14) . .
Br3 Ga3 Br2 111.22(4) . .
O1 Ga3 Br4 107.09(13) . .
Br3 Ga3 Br4 109.88(4) . .
Br2 Ga3 Br4 112.27(4) . .
C8 Cl1 C8 67.0(11) 2 .
Ga3 O1 Ga2 130.0(2) . .
Ga3 O1 Ga1 133.1(2) . .
Ga2 O1 Ga1 96.4(2) . .
C1 O2 Ga1 131.3(4) . .
C2 O3 Ga1 131.4(4) . .
C1 O4 C3 118.1(5) . .
C2 O5 C4 117.6(6) . .
O2 C1 O4 120.5(6) . .
O2 C1 C5 125.3(6) . .
O4 C1 C5 114.1(6) . .
O3 C2 O5 120.4(6) . .
O3 C2 C5 125.6(6) . .
O5 C2 C5 114.0(6) . .
O4 C3 H3A 109.5 . .
O4 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
O4 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O5 C4 H4A 109.5 . .
O5 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
O5 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C1 C5 C2 118.4(6) . .
C1 C5 C7 117.2(6) . .
C2 C5 C7 117.2(6) . .
C1 C5 C6 117.4(6) . .
C2 C5 C6 115.3(6) . .
C7 C5 C6 56.6(5) . .
C7 C6 C5 61.2(5) . .
C7 C6 H6A 117.7 . .
C5 C6 H6A 117.7 . .
C7 C6 H6B 117.7 . .
C5 C6 H6B 117.7 . .
H6A C6 H6B 114.8 . .
C6 C7 C5 62.3(5) . .
C6 C7 H7A 117.5 . .
C5 C7 H7A 117.5 . .
C6 C7 H7B 117.5 . .
C5 C7 H7B 117.5 . .
H7A C7 H7B 114.6 . .
Cl2 C8 Cl1 115.4(8) . .
Cl2 C8 H8A 108.4 . .
Cl1 C8 H8A 108.4 . .
Cl2 C8 H8B 108.4 . .
Cl1 C8 H8B 108.4 . .
H8A C8 H8B 107.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O1 1.904(4) 2_655
Ga1 O1 1.904(4) .
Ga1 O3 1.981(4) 2_655
Ga1 O3 1.981(4) .
Ga1 O2 1.992(4) 2_655
Ga1 O2 1.992(4) .
Ga1 Ga2 2.8125(14) .
Ga2 O1 1.868(4) 2_655
Ga2 O1 1.868(4) .
Ga2 Br1 2.2873(9) 2_655
Ga2 Br1 2.2873(9) .
Ga3 O1 1.831(5) .
Ga3 Br3 2.3140(10) .
Ga3 Br2 2.3235(11) .
Ga3 Br4 2.3260(10) .
Cl1 C8 1.779(17) 2
Cl1 C8 1.779(17) .
Cl2 C8 1.760(18) .
O2 C1 1.232(7) .
O3 C2 1.232(8) .
O4 C1 1.307(8) .
O4 C3 1.459(7) .
O5 C2 1.306(7) .
O5 C4 1.453(8) .
C1 C5 1.466(9) .
C2 C5 1.468(9) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C3 H3C 0.9800 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 C7 1.545(10) .
C5 C6 1.561(9) .
C6 C7 1.472(11) .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
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
Br3 Ga3 O1 Ga2 -129.0(3) .
Br2 Ga3 O1 Ga2 110.6(3) .
Br4 Ga3 O1 Ga2 -9.5(3) .
Br3 Ga3 O1 Ga1 60.0(3) .
Br2 Ga3 O1 Ga1 -60.4(3) .
Br4 Ga3 O1 Ga1 179.5(3) .
O1 Ga2 O1 Ga3 -173.4(4) 2_655
Br1 Ga2 O1 Ga3 -61.7(3) 2_655
Br1 Ga2 O1 Ga3 75.0(3) .
Ga1 Ga2 O1 Ga3 -173.4(4) .
O1 Ga2 O1 Ga1 0.000(0) 2_655
Br1 Ga2 O1 Ga1 111.73(14) 2_655
Br1 Ga2 O1 Ga1 -111.53(14) .
Ga1 O2 C1 O4 173.2(4) .
Ga1 O2 C1 C5 -6.3(10) .
C3 O4 C1 O2 0.2(10) .
C3 O4 C1 C5 179.7(6) .
Ga1 O3 C2 O5 179.9(4) .
Ga1 O3 C2 C5 0.2(10) .
C4 O5 C2 O3 0.6(10) .
C4 O5 C2 C5 -179.6(6) .
O2 C1 C5 C2 -4.7(11) .
O4 C1 C5 C2 175.9(6) .
O2 C1 C5 C7 -154.3(7) .
O4 C1 C5 C7 26.2(9) .
O2 C1 C5 C6 141.2(7) .
O4 C1 C5 C6 -38.2(9) .
O3 C2 C5 C1 7.8(11) .
O5 C2 C5 C1 -172.0(6) .
O3 C2 C5 C7 157.4(7) .
O5 C2 C5 C7 -22.4(9) .
O3 C2 C5 C6 -138.8(7) .
O5 C2 C5 C6 41.4(9) .
C1 C5 C6 C7 105.9(8) .
C2 C5 C6 C7 -107.2(7) .
C1 C5 C7 C6 -106.3(7) .
C2 C5 C7 C6 103.6(7) .
C8 Cl1 C8 Cl2 178.5(16) 2
