#------------------------------------------------------------------------------
#$Date: 2019-11-23 12:20:46 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233267 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/86/4348683.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_4348683
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 O2'
_chemical_formula_weight         1323.00
_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                 116.1000(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.5284(13)
_cell_length_b                   14.9322(8)
_cell_length_c                   21.9348(12)
_cell_measurement_reflns_used    900
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     6920.5(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0583
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_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            29337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.928
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998)'
_exptl_crystal_colour            dark_red
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       prism
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.876
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0499
_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)+(0.0567P)²+8.1420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5182
_reflns_number_total             6790
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ic6b01514_si_002.cif
_cod_data_source_block           gabian14m
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4348683
_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   0.789
_shelx_estimated_absorpt_t_max   0.922
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 0.53266(2) 0.61820(2) 0.71747(2) 0.01991(11) Uani 1 1 d . . .
N1 N 0.62719(11) 0.61415(16) 0.75805(12) 0.0201(5) Uani 1 1 d . . .
N2 N 0.53804(11) 0.67561(15) 0.63867(12) 0.0203(5) Uani 1 1 d . . .
O1 O 0.51098(10) 0.50246(13) 0.68480(10) 0.0216(5) Uani 1 1 d . . .
C1 C 0.64453(14) 0.63298(18) 0.70938(15) 0.0202(6) Uani 1 1 d . . .
C2 C 0.59709(14) 0.66456(18) 0.64547(14) 0.0190(6) Uani 1 1 d . . .
C3 C 0.62686(15) 0.68047(18) 0.60002(15) 0.0224(6) Uani 1 1 d . . .
C4 C 0.69155(15) 0.6567(2) 0.63830(15) 0.0236(7) Uani 1 1 d . . .
C5 C 0.70547(14) 0.63034(19) 0.70587(15) 0.0222(6) Uani 1 1 d . . .
C6 C 0.76697(15) 0.6099(2) 0.74930(16) 0.0269(7) Uani 1 1 d . . .
H6A H 0.7784 0.5945 0.7952 0.032 Uiso 1 1 calc R U .
C7 C 0.81316(15) 0.6124(2) 0.72434(18) 0.0312(7) Uani 1 1 d . . .
H7A H 0.8558 0.5986 0.7544 0.037 Uiso 1 1 calc R U .
C8 C 0.79858(17) 0.6340(2) 0.65826(18) 0.0332(8) Uani 1 1 d . . .
H8A H 0.8307 0.6329 0.6431 0.040 Uiso 1 1 calc R U .
C9 C 0.73579(16) 0.6578(2) 0.61262(17) 0.0277(7) Uani 1 1 d . . .
C10 C 0.71283(17) 0.6832(2) 0.54321(17) 0.0311(8) Uani 1 1 d . . .
H10A H 0.7406 0.6827 0.5223 0.037 Uiso 1 1 calc R U .
C11 C 0.65082(17) 0.7085(2) 0.50638(17) 0.0312(8) Uani 1 1 d . . .
H11A H 0.6371 0.7270 0.4606 0.037 Uiso 1 1 calc R U .
C12 C 0.60650(16) 0.7081(2) 0.53389(16) 0.0265(7) Uani 1 1 d . . .
H12A H 0.5639 0.7263 0.5074 0.032 Uiso 1 1 calc R U .
C13 C 0.67683(14) 0.60068(19) 0.82594(15) 0.0212(6) Uani 1 1 d . . .
C14 C 0.69914(14) 0.5142(2) 0.84799(15) 0.0221(6) Uani 1 1 d . . .
C15 C 0.74973(14) 0.5050(2) 0.91287(16) 0.0269(7) Uani 1 1 d . . .
H15A H 0.7662 0.4471 0.9292 0.032 Uiso 1 1 calc R U .
C16 C 0.77582(15) 0.5792(2) 0.95315(16) 0.0306(7) Uani 1 1 d . . .
H16A H 0.8100 0.5721 0.9970 0.037 Uiso 1 1 calc R U .
C17 C 0.75235(15) 0.6641(2) 0.92996(16) 0.0283(7) Uani 1 1 d . . .
H17A H 0.7707 0.7145 0.9583 0.034 Uiso 1 1 calc R U .
C18 C 0.70244(14) 0.6769(2) 0.86596(15) 0.0233(7) Uani 1 1 d . . .
C19 C 0.67085(15) 0.4309(2) 0.80524(16) 0.0260(7) Uani 1 1 d . . .
H19A H 0.6311 0.4489 0.7650 0.031 Uiso 1 1 calc R U .
C20 C 0.71593(19) 0.3897(2) 0.7792(2) 0.0402(9) Uani 1 1 d . . .
H20A H 0.7238 0.4330 0.7502 0.060 Uiso 1 1 calc R U .
H20B H 0.6967 0.3356 0.7529 0.060 Uiso 1 1 calc R U .
H20C H 0.7561 0.3741 0.8179 0.060 Uiso 1 1 calc R U .
C21 C 0.65372(15) 0.3609(2) 0.84533(16) 0.0283(7) Uani 1 1 d . . .
H21A H 0.6257 0.3879 0.8626 0.042 Uiso 1 1 calc R U .
H21B H 0.6924 0.3395 0.8835 0.042 Uiso 1 1 calc R U .
H21C H 0.6321 0.3104 0.8156 0.042 Uiso 1 1 calc R U .
C22 C 0.67631(15) 0.7702(2) 0.84173(15) 0.0253(7) Uani 1 1 d . . .
H22A H 0.6518 0.7685 0.7912 0.030 Uiso 1 1 calc R U .
C23 C 0.63152(18) 0.7968(2) 0.87131(19) 0.0386(9) Uani 1 1 d . . .
H23A H 0.5957 0.7551 0.8554 0.058 Uiso 1 1 calc R U .
H23B H 0.6160 0.8577 0.8567 0.058 Uiso 1 1 calc R U .
H23C H 0.6539 0.7948 0.9210 0.058 Uiso 1 1 calc R U .
C24 C 0.72869(19) 0.8413(3) 0.8600(2) 0.0523(11) Uani 1 1 d . . .
H24A H 0.7098 0.8986 0.8393 0.079 Uiso 1 1 calc R U .
H24B H 0.7589 0.8223 0.8429 0.079 Uiso 1 1 calc R U .
H24C H 0.7508 0.8481 0.9094 0.079 Uiso 1 1 calc R U .
C25 C 0.49507(14) 0.72788(18) 0.58176(14) 0.0192(6) Uani 1 1 d . . .
C26 C 0.44553(14) 0.68557(19) 0.52763(14) 0.0196(6) Uani 1 1 d . . .
C27 C 0.40564(14) 0.7391(2) 0.47304(15) 0.0232(6) Uani 1 1 d . . .
H27A H 0.3714 0.7120 0.4357 0.028 Uiso 1 1 calc R U .
C28 C 0.41497(14) 0.8307(2) 0.47235(15) 0.0246(7) Uani 1 1 d . . .
H28A H 0.3872 0.8658 0.4350 0.030 Uiso 1 1 calc R U .
C29 C 0.46476(14) 0.87059(19) 0.52619(15) 0.0223(6) Uani 1 1 d . . .
H29A H 0.4709 0.9334 0.5253 0.027 Uiso 1 1 calc R U .
C30 C 0.50613(14) 0.82093(19) 0.58173(15) 0.0202(6) Uani 1 1 d . . .
C31 C 0.43444(14) 0.58560(19) 0.52661(14) 0.0204(6) Uani 1 1 d . . .
H31A H 0.4736 0.5575 0.5621 0.024 Uiso 1 1 calc R U .
C32 C 0.42154(18) 0.5436(2) 0.45787(17) 0.0347(8) Uani 1 1 d . . .
H32A H 0.4558 0.5596 0.4459 0.052 Uiso 1 1 calc R U .
H32B H 0.3812 0.5662 0.4229 0.052 Uiso 1 1 calc R U .
H32C H 0.4194 0.4783 0.4609 0.052 Uiso 1 1 calc R U .
C33 C 0.37991(18) 0.5646(2) 0.5440(2) 0.0402(9) Uani 1 1 d . . .
H33A H 0.3903 0.5861 0.5899 0.060 Uiso 1 1 calc R U .
H33B H 0.3730 0.4997 0.5418 0.060 Uiso 1 1 calc R U .
H33C H 0.3414 0.5944 0.5113 0.060 Uiso 1 1 calc R U .
C34 C 0.56012(14) 0.86684(19) 0.64093(15) 0.0230(7) Uani 1 1 d . . .
H34A H 0.5957 0.8229 0.6607 0.028 Uiso 1 1 calc R U .
C35 C 0.53928(16) 0.8896(2) 0.69614(16) 0.0291(7) Uani 1 1 d . . .
H35A H 0.5289 0.8343 0.7131 0.044 Uiso 1 1 calc R U .
H35B H 0.5019 0.9284 0.6771 0.044 Uiso 1 1 calc R U .
H35C H 0.5737 0.9206 0.7336 0.044 Uiso 1 1 calc R U .
C36 C 0.58551(17) 0.9502(2) 0.62038(18) 0.0343(8) Uani 1 1 d . . .
H36A H 0.5961 0.9351 0.5831 0.051 Uiso 1 1 calc R U .
H36B H 0.6235 0.9716 0.6593 0.051 Uiso 1 1 calc R U .
H36C H 0.5532 0.9972 0.6056 0.051 Uiso 1 1 calc R U .
C37 C 0.50486(13) 0.43368(18) 0.72118(14) 0.0177(6) Uani 1 1 d . . .
C38 C 0.50717(13) 0.34004(19) 0.70095(14) 0.0188(6) Uani 1 1 d . . .
C39 C 0.51479(14) 0.2988(2) 0.64947(15) 0.0240(7) Uani 1 1 d . . .
H39A H 0.5204 0.3328 0.6159 0.029 Uiso 1 1 calc R U .
C40 C 0.51409(16) 0.2031(2) 0.64731(17) 0.0287(7) Uani 1 1 d . . .
H40A H 0.5186 0.1740 0.6112 0.034 Uiso 1 1 calc R U .
C41 C 0.50714(16) 0.1518(2) 0.69537(17) 0.0292(7) Uani 1 1 d . . .
H41A H 0.5071 0.0883 0.6922 0.035 Uiso 1 1 calc R U .
C42 C 0.5000 0.1930(3) 0.7500 0.0217(9) Uani 1 2 d S T P
C43 C 0.5000 0.2859(3) 0.7500 0.0183(8) 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
O1 Ga1 N2 100.27(9) . .
O1 Ga1 N1 101.93(9) . .
N2 Ga1 N1 85.18(10) . .
O1 Ga1 Ga1 94.96(6) . 2_656
N2 Ga1 Ga1 141.61(7) . 2_656
N1 Ga1 Ga1 125.79(7) . 2_656
C1 N1 C13 117.5(2) . .
C1 N1 Ga1 108.07(18) . .
C13 N1 Ga1 134.31(19) . .
C2 N2 C25 117.4(2) . .
C2 N2 Ga1 108.08(18) . .
C25 N2 Ga1 134.4(2) . .
C37 O1 Ga1 124.38(18) . .
N1 C1 C2 118.2(3) . .
N1 C1 C5 133.4(3) . .
C2 C1 C5 108.4(3) . .
N2 C2 C1 118.2(3) . .
N2 C2 C3 133.3(3) . .
C1 C2 C3 108.6(3) . .
C12 C3 C4 118.9(3) . .
C12 C3 C2 135.7(3) . .
C4 C3 C2 105.4(3) . .
C9 C4 C3 123.9(3) . .
C9 C4 C5 123.8(3) . .
C3 C4 C5 112.3(3) . .
C6 C5 C4 118.2(3) . .
C6 C5 C1 136.5(3) . .
C4 C5 C1 105.3(3) . .
C5 C6 C7 118.7(3) . .
C8 C7 C6 122.4(3) . .
C7 C8 C9 120.2(3) . .
C4 C9 C8 116.5(3) . .
C4 C9 C10 116.0(3) . .
C8 C9 C10 127.5(3) . .
C11 C10 C9 120.5(3) . .
C10 C11 C12 122.6(3) . .
C3 C12 C11 118.1(3) . .
C14 C13 C18 122.7(3) . .
C14 C13 N1 119.7(3) . .
C18 C13 N1 117.5(3) . .
C13 C14 C15 117.6(3) . .
C13 C14 C19 123.1(3) . .
C15 C14 C19 119.3(3) . .
C16 C15 C14 120.6(3) . .
C15 C16 C17 120.4(3) . .
C16 C17 C18 121.2(3) . .
C17 C18 C13 117.4(3) . .
C17 C18 C22 120.7(3) . .
C13 C18 C22 121.9(3) . .
C14 C19 C21 111.0(3) . .
C14 C19 C20 111.7(3) . .
C21 C19 C20 109.8(3) . .
C23 C22 C18 109.9(3) . .
C23 C22 C24 109.6(3) . .
C18 C22 C24 112.7(3) . .
C26 C25 C30 122.0(3) . .
C26 C25 N2 119.8(2) . .
C30 C25 N2 118.2(3) . .
C25 C26 C27 117.6(3) . .
C25 C26 C31 122.2(3) . .
C27 C26 C31 120.2(3) . .
C28 C27 C26 121.5(3) . .
C29 C28 C27 119.7(3) . .
C28 C29 C30 121.5(3) . .
C29 C30 C25 117.8(3) . .
C29 C30 C34 120.4(3) . .
C25 C30 C34 121.8(3) . .
C26 C31 C33 111.0(2) . .
C26 C31 C32 112.1(2) . .
C33 C31 C32 109.7(3) . .
C30 C34 C35 109.7(3) . .
C30 C34 C36 113.7(3) . .
C35 C34 C36 110.8(3) . .
O1 C37 C37 130.30(15) . 2_656
O1 C37 C38 121.1(2) . .
C37 C37 C38 108.56(15) 2_656 .
C39 C38 C43 118.3(3) . .
C39 C38 C37 135.4(3) . .
C43 C38 C37 106.3(3) . .
C38 C39 C40 118.3(3) . .
C41 C40 C39 122.5(3) . .
C40 C41 C42 120.4(3) . .
C43 C42 C41 115.7(2) . 2_656
C43 C42 C41 115.6(2) . .
C41 C42 C41 128.7(4) 2_656 .
C42 C43 C38 124.89(18) . .
C42 C43 C38 124.89(18) . 2_656
C38 C43 C38 110.2(4) . 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O1 1.8545(19) .
Ga1 N2 1.983(2) .
Ga1 N1 2.000(2) .
Ga1 Ga1 2.5157(7) 2_656
N1 C1 1.330(4) .
N1 C13 1.446(4) .
N2 C2 1.341(4) .
N2 C25 1.442(3) .
O1 C37 1.347(3) .
C1 C2 1.434(4) .
C1 C5 1.470(4) .
C2 C3 1.468(4) .
C3 C12 1.376(4) .
C3 C4 1.422(4) .
C4 C9 1.385(4) .
C4 C5 1.425(4) .
C5 C6 1.372(4) .
C6 C7 1.416(5) .
C7 C8 1.373(5) .
C8 C9 1.418(5) .
C9 C10 1.425(4) .
C10 C11 1.373(5) .
C11 C12 1.416(5) .
C13 C14 1.398(4) .
C13 C18 1.401(4) .
C14 C15 1.404(4) .
C14 C19 1.523(4) .
C15 C16 1.382(5) .
C16 C17 1.386(5) .
C17 C18 1.391(4) .
C18 C22 1.522(4) .
C19 C21 1.530(4) .
C19 C20 1.537(4) .
C22 C23 1.514(5) .
C22 C24 1.540(5) .
C25 C26 1.396(4) .
C25 C30 1.414(4) .
C26 C27 1.402(4) .
C26 C31 1.514(4) .
C27 C28 1.386(4) .
C28 C29 1.380(4) .
C29 C30 1.392(4) .
C30 C34 1.523(4) .
C31 C33 1.523(4) .
C31 C32 1.535(4) .
C34 C35 1.531(4) .
C34 C36 1.532(4) .
C37 C37 1.380(6) 2_656
C37 C38 1.475(4) .
C38 C39 1.365(4) .
C38 C43 1.414(4) .
C39 C40 1.430(4) .
C40 C41 1.370(4) .
C41 C42 1.421(4) .
C42 C43 1.387(6) .
C42 C41 1.421(4) 2_656
C43 C38 1.414(4) 2_656
