#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:21:23 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233269 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/86/4348684.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_4348684
loop_
_publ_author_name
'Fedushkin, Igor L.'
'Skatova, Alexandra A.'
'Dodonov, Vladimir A.'
'Yang, Xiao-Juan'
'Chudakova, Valentina A.'
'Piskunov, Alexander V.'
'Demeshko, Serhiy'
'Baranov, Evgeny V.'
_publ_section_title
;
 Ligand "Brackets" for Ga-Ga Bond.
;
_journal_issue                   17
_journal_name_full               'Inorganic chemistry'
_journal_page_first              9047
_journal_page_last               9056
_journal_paper_doi               10.1021/acs.inorgchem.6b01514
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C84 H86 Ga2 N4 O3'
_chemical_formula_weight         1339.00
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 117.365(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.8688(4)
_cell_length_b                   14.9155(3)
_cell_length_c                   22.1366(4)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     6999.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            29813
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.716
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.823
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998)'
_exptl_crystal_colour            dark_red
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       prism
_exptl_crystal_F_000             2816
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         6865
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0344
_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)+(0.0513P)²+4.4806P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5831
_reflns_number_total             6865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b01514_si_004.cif
_cod_data_source_block           gabian13m
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4348684
_shelx_shelxl_version_number     2014/7
_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   0.790
_shelx_estimated_absorpt_t_max   0.880
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 0.53835(2) 0.61859(2) 0.71080(2) 0.01601(8) Uani 1 1 d . . .
N1 N 0.63078(7) 0.61188(10) 0.75359(8) 0.0181(3) Uani 1 1 d . . .
N2 N 0.54262(7) 0.67354(10) 0.63268(7) 0.0173(3) Uani 1 1 d . . .
O1 O 0.50582(6) 0.50636(9) 0.68277(6) 0.0233(3) Uani 1 1 d . . .
O2 O 0.5000 0.68077(12) 0.7500 0.0208(4) Uani 1 2 d S T P
C1 C 0.64858(9) 0.63166(12) 0.70634(9) 0.0178(4) Uani 1 1 d . . .
C2 C 0.60159(9) 0.66398(12) 0.64166(9) 0.0180(4) Uani 1 1 d . . .
C3 C 0.63158(9) 0.68072(12) 0.59833(9) 0.0191(4) Uani 1 1 d . . .
C4 C 0.69591(9) 0.65612(12) 0.63797(10) 0.0205(4) Uani 1 1 d . . .
C5 C 0.70942(9) 0.62935(12) 0.70486(10) 0.0205(4) Uani 1 1 d . . .
C6 C 0.77071(9) 0.60764(13) 0.74988(11) 0.0249(4) Uani 1 1 d . . .
H6A H 0.7817 0.5916 0.7955 0.030 Uiso 1 1 calc R U .
C7 C 0.81698(10) 0.60985(13) 0.72661(12) 0.0291(5) Uani 1 1 d . . .
H7A H 0.8594 0.5955 0.7576 0.035 Uiso 1 1 calc R U .
C8 C 0.80272(10) 0.63193(14) 0.66090(12) 0.0298(5) Uani 1 1 d . . .
H8A H 0.8349 0.6308 0.6470 0.036 Uiso 1 1 calc R U .
C9 C 0.74022(10) 0.65656(13) 0.61351(11) 0.0248(4) Uani 1 1 d . . .
C10 C 0.71766(10) 0.68262(14) 0.54433(11) 0.0284(5) Uani 1 1 d . . .
H10A H 0.7455 0.6821 0.5245 0.034 Uiso 1 1 calc R U .
C11 C 0.65613(10) 0.70836(14) 0.50626(10) 0.0278(5) Uani 1 1 d . . .
H11A H 0.6426 0.7266 0.4605 0.033 Uiso 1 1 calc R U .
C12 C 0.61190(10) 0.70881(13) 0.53231(10) 0.0228(4) Uani 1 1 d . . .
H12A H 0.5697 0.7280 0.5050 0.027 Uiso 1 1 calc R U .
C13 C 0.67845(9) 0.59876(13) 0.82268(9) 0.0195(4) Uani 1 1 d . . .
C14 C 0.70204(9) 0.67554(13) 0.86380(10) 0.0229(4) Uani 1 1 d . . .
C15 C 0.75057(10) 0.66355(14) 0.92921(10) 0.0276(4) Uani 1 1 d . . .
H15A H 0.7676 0.7143 0.9578 0.033 Uiso 1 1 calc R U .
C16 C 0.77475(10) 0.57899(15) 0.95368(10) 0.0291(5) Uani 1 1 d . . .
H16A H 0.8085 0.5723 0.9983 0.035 Uiso 1 1 calc R U .
C17 C 0.74956(9) 0.50460(14) 0.91289(10) 0.0269(4) Uani 1 1 d . . .
H17A H 0.7660 0.4469 0.9302 0.032 Uiso 1 1 calc R U .
C18 C 0.70051(9) 0.51236(13) 0.84679(10) 0.0227(4) Uani 1 1 d . . .
C19 C 0.67493(10) 0.76864(13) 0.83899(10) 0.0255(4) Uani 1 1 d . . .
H19A H 0.6475 0.7655 0.7887 0.031 Uiso 1 1 calc R U .
C20 C 0.63448(11) 0.79796(16) 0.87159(12) 0.0370(5) Uani 1 1 d . . .
H20A H 0.5993 0.7560 0.8591 0.056 Uiso 1 1 calc R U .
H20B H 0.6180 0.8583 0.8557 0.056 Uiso 1 1 calc R U .
H20C H 0.6600 0.7986 0.9212 0.056 Uiso 1 1 calc R U .
C21 C 0.72673(13) 0.83826(17) 0.85299(17) 0.0534(7) Uani 1 1 d . . .
H21A H 0.7073 0.8960 0.8333 0.080 Uiso 1 1 calc R U .
H21B H 0.7532 0.8184 0.8324 0.080 Uiso 1 1 calc R U .
H21C H 0.7527 0.8449 0.9022 0.080 Uiso 1 1 calc R U .
C22 C 0.67233(10) 0.42904(13) 0.80395(11) 0.0267(4) Uani 1 1 d . . .
H22A H 0.6329 0.4471 0.7628 0.032 Uiso 1 1 calc R U .
C23 C 0.71713(13) 0.38663(15) 0.77976(14) 0.0416(6) Uani 1 1 d . . .
H23A H 0.7256 0.4297 0.7516 0.062 Uiso 1 1 calc R U .
H23B H 0.6975 0.3328 0.7530 0.062 Uiso 1 1 calc R U .
H23C H 0.7568 0.3703 0.8193 0.062 Uiso 1 1 calc R U .
C24 C 0.65463(10) 0.36010(14) 0.84337(11) 0.0281(4) Uani 1 1 d . . .
H24A H 0.6272 0.3882 0.8600 0.042 Uiso 1 1 calc R U .
H24B H 0.6930 0.3379 0.8820 0.042 Uiso 1 1 calc R U .
H24C H 0.6323 0.3099 0.8133 0.042 Uiso 1 1 calc R U .
C25 C 0.49824(8) 0.72687(12) 0.57696(9) 0.0175(4) Uani 1 1 d . . .
C26 C 0.50858(9) 0.82015(12) 0.57860(9) 0.0195(4) Uani 1 1 d . . .
C27 C 0.46589(9) 0.87122(13) 0.52437(10) 0.0232(4) Uani 1 1 d . . .
H27A H 0.4719 0.9342 0.5242 0.028 Uiso 1 1 calc R U .
C28 C 0.41468(9) 0.83169(14) 0.47044(10) 0.0251(4) Uani 1 1 d . . .
H28A H 0.3863 0.8674 0.4335 0.030 Uiso 1 1 calc R U .
C29 C 0.40500(9) 0.74054(13) 0.47038(10) 0.0238(4) Uani 1 1 d . . .
H29A H 0.3695 0.7142 0.4335 0.029 Uiso 1 1 calc R U .
C30 C 0.44644(9) 0.68608(13) 0.52369(9) 0.0195(4) Uani 1 1 d . . .
C31 C 0.56227(9) 0.86586(13) 0.63915(10) 0.0227(4) Uani 1 1 d . . .
H31A H 0.5972 0.8213 0.6608 0.027 Uiso 1 1 calc R U .
C32 C 0.53976(11) 0.89092(14) 0.69175(11) 0.0298(5) Uani 1 1 d . . .
H32A H 0.5265 0.8366 0.7066 0.045 Uiso 1 1 calc R U .
H32B H 0.5041 0.9325 0.6712 0.045 Uiso 1 1 calc R U .
H32C H 0.5743 0.9196 0.7310 0.045 Uiso 1 1 calc R U .
C33 C 0.58901(11) 0.94793(14) 0.61953(11) 0.0335(5) Uani 1 1 d . . .
H33A H 0.5988 0.9319 0.5825 0.050 Uiso 1 1 calc R U .
H33B H 0.6275 0.9680 0.6590 0.050 Uiso 1 1 calc R U .
H33C H 0.5578 0.9963 0.6045 0.050 Uiso 1 1 calc R U .
C34 C 0.43373(9) 0.58589(13) 0.52272(10) 0.0225(4) Uani 1 1 d . . .
H34A H 0.4726 0.5569 0.5585 0.027 Uiso 1 1 calc R U .
C35 C 0.41965(12) 0.54343(14) 0.45451(11) 0.0356(5) Uani 1 1 d . . .
H35A H 0.4151 0.4784 0.4571 0.053 Uiso 1 1 calc R U .
H35B H 0.4544 0.5561 0.4438 0.053 Uiso 1 1 calc R U .
H35C H 0.3804 0.5685 0.4188 0.053 Uiso 1 1 calc R U .
C36 C 0.37998(11) 0.56804(15) 0.54022(13) 0.0360(5) Uani 1 1 d . . .
H36A H 0.3911 0.5920 0.5855 0.054 Uiso 1 1 calc R U .
H36B H 0.3728 0.5033 0.5398 0.054 Uiso 1 1 calc R U .
H36C H 0.3415 0.5973 0.5066 0.054 Uiso 1 1 calc R U .
C37 C 0.50331(8) 0.43710(12) 0.72087(9) 0.0179(4) Uani 1 1 d . . .
C38 C 0.50554(8) 0.34359(12) 0.70063(9) 0.0188(4) Uani 1 1 d . . .
C39 C 0.51148(9) 0.30228(13) 0.64867(10) 0.0240(4) Uani 1 1 d . . .
H39A H 0.5156 0.3364 0.6147 0.029 Uiso 1 1 calc R U .
C40 C 0.51126(10) 0.20652(14) 0.64680(11) 0.0297(5) Uani 1 1 d . . .
H40A H 0.5150 0.1775 0.6106 0.036 Uiso 1 1 calc R U .
C41 C 0.50587(10) 0.15469(13) 0.69499(11) 0.0286(5) Uani 1 1 d . . .
H41A H 0.5060 0.0912 0.6919 0.034 Uiso 1 1 calc R U .
C42 C 0.5000 0.19653(18) 0.7500 0.0236(6) Uani 1 2 d S T P
C43 C 0.5000 0.28952(17) 0.7500 0.0191(5) Uani 1 2 d S T 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'
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'
Ga Ga 0.2307 1.6083 '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
O2 Ga1 O1 114.08(6) . .
O2 Ga1 N2 117.30(6) . .
O1 Ga1 N2 105.65(6) . .
O2 Ga1 N1 120.39(5) . .
O1 Ga1 N1 108.95(6) . .
N2 Ga1 N1 86.81(6) . .
C1 N1 C13 118.89(15) . .
C1 N1 Ga1 107.67(12) . .
C13 N1 Ga1 133.14(12) . .
C2 N2 C25 119.75(15) . .
C2 N2 Ga1 107.64(12) . .
C25 N2 Ga1 132.15(12) . .
C37 O1 Ga1 128.40(11) . .
Ga1 O2 Ga1 117.34(10) 2_656 .
N1 C1 C2 118.21(16) . .
N1 C1 C5 133.56(17) . .
C2 C1 C5 108.22(16) . .
N2 C2 C1 118.08(16) . .
N2 C2 C3 133.33(17) . .
C1 C2 C3 108.59(16) . .
C12 C3 C4 118.52(17) . .
C12 C3 C2 135.92(18) . .
C4 C3 C2 105.48(16) . .
C9 C4 C5 123.89(18) . .
C9 C4 C3 123.81(18) . .
C5 C4 C3 112.29(17) . .
C6 C5 C4 118.50(18) . .
C6 C5 C1 136.20(18) . .
C4 C5 C1 105.29(16) . .
C5 C6 C7 118.51(19) . .
C8 C7 C6 122.4(2) . .
C7 C8 C9 120.57(19) . .
C4 C9 C8 116.03(19) . .
C4 C9 C10 116.11(19) . .
C8 C9 C10 127.86(19) . .
C11 C10 C9 120.45(18) . .
C10 C11 C12 122.66(19) . .
C3 C12 C11 118.40(19) . .
C18 C13 C14 122.19(17) . .
C18 C13 N1 120.31(17) . .
C14 C13 N1 117.50(16) . .
C15 C14 C13 117.58(18) . .
C15 C14 C19 120.37(18) . .
C13 C14 C19 122.03(17) . .
C14 C15 C16 121.43(19) . .
C17 C16 C15 119.76(18) . .
C16 C17 C18 121.44(19) . .
C17 C18 C13 117.54(18) . .
C17 C18 C22 120.23(18) . .
C13 C18 C22 122.22(17) . .
C20 C19 C14 110.50(17) . .
C20 C19 C21 109.89(19) . .
C14 C19 C21 112.02(18) . .
C18 C22 C24 110.68(17) . .
C18 C22 C23 112.03(18) . .
C24 C22 C23 109.97(17) . .
C30 C25 C26 121.88(17) . .
C30 C25 N2 119.98(16) . .
C26 C25 N2 118.14(16) . .
C27 C26 C25 117.89(17) . .
C27 C26 C31 120.00(17) . .
C25 C26 C31 122.02(17) . .
C28 C27 C26 121.06(18) . .
C29 C28 C27 120.05(18) . .
C28 C29 C30 121.23(18) . .
C25 C30 C29 117.88(17) . .
C25 C30 C34 122.20(17) . .
C29 C30 C34 119.92(17) . .
C26 C31 C33 113.53(16) . .
C26 C31 C32 109.26(16) . .
C33 C31 C32 110.90(17) . .
C30 C34 C36 110.68(16) . .
C30 C34 C35 111.91(16) . .
C36 C34 C35 110.53(18) . .
O1 C37 C37 130.14(9) . 2_656
O1 C37 C38 121.03(16) . .
C37 C37 C38 108.80(10) 2_656 .
C39 C38 C43 118.42(18) . .
C39 C38 C37 135.56(18) . .
C43 C38 C37 106.02(16) . .
C38 C39 C40 118.30(18) . .
C41 C40 C39 122.80(19) . .
C40 C41 C42 119.81(19) . .
C43 C42 C41 115.85(13) . .
C43 C42 C41 115.85(13) . 2_656
C41 C42 C41 128.3(3) . 2_656
C42 C43 C38 124.82(11) . .
C42 C43 C38 124.81(11) . 2_656
C38 C43 C38 110.4(2) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O2 1.7836(9) .
Ga1 O1 1.8294(13) .
Ga1 N2 1.9582(15) .
Ga1 N1 1.9630(16) .
N1 C1 1.331(2) .
N1 C13 1.440(2) .
N2 C2 1.336(2) .
N2 C25 1.441(2) .
O1 C37 1.352(2) .
O2 Ga1 1.7835(9) 2_656
C1 C2 1.437(3) .
C1 C5 1.468(3) .
C2 C3 1.458(3) .
C3 C12 1.379(3) .
C3 C4 1.423(3) .
C4 C9 1.392(3) .
C4 C5 1.420(3) .
C5 C6 1.377(3) .
C6 C7 1.417(3) .
C7 C8 1.373(3) .
C8 C9 1.422(3) .
C9 C10 1.424(3) .
C10 C11 1.370(3) .
C11 C12 1.417(3) .
C13 C18 1.402(3) .
C13 C14 1.409(3) .
C14 C15 1.389(3) .
C14 C19 1.524(3) .
C15 C16 1.389(3) .
C16 C17 1.382(3) .
C17 C18 1.396(3) .
C18 C22 1.520(3) .
C19 C20 1.512(3) .
C19 C21 1.533(3) .
C22 C24 1.528(3) .
C22 C23 1.535(3) .
C25 C30 1.396(3) .
C25 C26 1.411(3) .
C26 C27 1.391(3) .
C26 C31 1.525(3) .
C27 C28 1.388(3) .
C28 C29 1.379(3) .
C29 C30 1.399(3) .
C30 C34 1.523(3) .
C31 C33 1.533(3) .
C31 C32 1.536(3) .
C34 C36 1.524(3) .
C34 C35 1.526(3) .
C37 C37 1.370(4) 2_656
C37 C38 1.473(3) .
C38 C39 1.368(3) .
C38 C43 1.413(2) .
C39 C40 1.429(3) .
C40 C41 1.371(3) .
C41 C42 1.431(2) .
C42 C43 1.387(4) .
C42 C41 1.431(2) 2_656
C43 C38 1.413(2) 2_656
