#------------------------------------------------------------------------------
#$Date: 2020-09-06 12:32:37 +0300 (Sun, 06 Sep 2020) $
#$Revision: 256062 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/48/7704887.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_7704887
loop_
_publ_author_name
'Hock, Andreas'
'Werner, Luis'
'Luz, Christian'
'Radius, Udo'
_publ_section_title
;
 N-Heterocyclic carbene and cyclic (alkyl)(amino)carbene adducts of
 gallium hydrides, gallium chlorides and gallium hydrochlorides.
;
_journal_issue                   32
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11108
_journal_page_last               11119
_journal_paper_doi               10.1039/d0dt02070b
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C11 H21 Cl2 Ga N2'
_chemical_formula_sum            'C11 H21 Cl2 Ga N2'
_chemical_formula_weight         321.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2020-06-08 deposited with the CCDC.	2020-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.6090(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0953(2)
_cell_length_b                   9.46110(10)
_cell_length_c                   11.53480(10)
_cell_measurement_reflns_used    13423
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3640
_cell_measurement_theta_min      5.6980
_cell_volume                     1481.52(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14130
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.015
_diffrn_reflns_theta_min         5.700
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    5.675
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.368
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
'CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics,implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.23(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0328
_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)+(0.0659P)²+1.0524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0864
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2519
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt02070b2.cif
_cod_data_source_block           compound_12
_cod_depositor_comments
'Adding full bibliography for 7704887--7704897.cif.'
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               7704887
_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.
;
_shelxl_version_number           2014/6
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'
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 0.48753(4) 0.22209(5) 0.47085(4) 0.02183(18) Uani 1 1 d . . . . .
Cl2 Cl 0.63691(9) 0.17025(12) 0.45510(9) 0.0276(3) Uani 1 1 d . . . . .
Cl3 Cl 0.48067(9) 0.13872(12) 0.64774(11) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.408(6) 0.150(9) 0.374(7) 0.05(2) Uiso 1 1 d . . . . .
N4 N 0.5545(3) 0.5128(4) 0.5652(3) 0.0164(7) Uani 1 1 d . . . . .
N7 N 0.4161(3) 0.5289(4) 0.4289(3) 0.0162(7) Uani 1 1 d . . . . .
C8 C 0.4842(3) 0.4341(4) 0.4891(3) 0.0167(8) Uani 1 1 d . . . . .
C6 C 0.4449(3) 0.6654(4) 0.4661(4) 0.0187(9) Uani 1 1 d . . . . .
C5 C 0.5323(3) 0.6555(4) 0.5519(4) 0.0182(8) Uani 1 1 d . . . . .
C12 C 0.3245(3) 0.4954(5) 0.3330(4) 0.0233(9) Uani 1 1 d . . . . .
H12 H 0.2859 0.5829 0.3169 0.028 Uiso 1 1 calc R U . . .
C9 C 0.6401(3) 0.4471(4) 0.6539(4) 0.0188(8) Uani 1 1 d . . . . .
H9 H 0.6346 0.3449 0.6403 0.023 Uiso 1 1 calc R U . . .
C16 C 0.5955(4) 0.7735(5) 0.6171(5) 0.0260(10) Uani 1 1 d . . . . .
H16A H 0.6162 0.7526 0.7016 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5584 0.8599 0.6045 0.039 Uiso 1 1 calc R U . . .
H16C H 0.6523 0.7837 0.5868 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3861(4) 0.7938(5) 0.4172(5) 0.0244(10) Uani 1 1 d . . . . .
H15A H 0.3845 0.8055 0.3340 0.037 Uiso 1 1 calc R U . . .
H15B H 0.4159 0.8754 0.4619 0.037 Uiso 1 1 calc R U . . .
H15C H 0.3202 0.7830 0.4242 0.037 Uiso 1 1 calc R U . . .
C11 C 0.6346(4) 0.4720(5) 0.7823(4) 0.0251(9) Uani 1 1 d . . . . .
H11A H 0.6379 0.5716 0.7989 0.038 Uiso 1 1 calc R U . . .
H11B H 0.6888 0.4253 0.8374 0.038 Uiso 1 1 calc R U . . .
H11C H 0.5738 0.4348 0.7916 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3492(4) 0.4560(7) 0.2172(5) 0.0374(12) Uani 1 1 d . . . . .
H14A H 0.3862 0.5309 0.1941 0.056 Uiso 1 1 calc R U . . .
H14B H 0.2893 0.4412 0.1548 0.056 Uiso 1 1 calc R U . . .
H14C H 0.3875 0.3707 0.2292 0.056 Uiso 1 1 calc R U . . .
C13 C 0.2612(4) 0.3867(5) 0.3745(5) 0.0288(10) Uani 1 1 d . . . . .
H13A H 0.2926 0.2959 0.3812 0.043 Uiso 1 1 calc R U . . .
H13B H 0.1978 0.3815 0.3170 0.043 Uiso 1 1 calc R U . . .
H13C H 0.2532 0.4141 0.4514 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7379(3) 0.4922(6) 0.6325(4) 0.0273(10) Uani 1 1 d . . . . .
H10A H 0.7359 0.4768 0.5496 0.041 Uiso 1 1 calc R U . . .
H10B H 0.7903 0.4374 0.6829 0.041 Uiso 1 1 calc R U . . .
H10C H 0.7490 0.5906 0.6515 0.041 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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga -1.2846 0.7763 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
C8 Ga1 Cl3 104.46(11) . . ?
C8 Ga1 Cl2 106.11(14) . . ?
Cl3 Ga1 Cl2 105.95(5) . . ?
C8 Ga1 H3 120(3) . . ?
Cl3 Ga1 H3 108(3) . . ?
Cl2 Ga1 H3 112(3) . . ?
C8 N4 C5 111.1(4) . . ?
C8 N4 C9 122.1(3) . . ?
C5 N4 C9 126.8(3) . . ?
C8 N7 C6 110.4(3) . . ?
C8 N7 C12 126.2(4) . . ?
C6 N7 C12 123.4(4) . . ?
N4 C8 N7 105.1(3) . . ?
N4 C8 Ga1 125.5(3) . . ?
N7 C8 Ga1 129.4(3) . . ?
C5 C6 N7 107.1(4) . . ?
C5 C6 C15 129.2(4) . . ?
N7 C6 C15 123.7(4) . . ?
C6 C5 N4 106.3(4) . . ?
C6 C5 C16 127.9(4) . . ?
N4 C5 C16 125.8(4) . . ?
N7 C12 C14 110.4(4) . . ?
N7 C12 C13 112.0(4) . . ?
C14 C12 C13 113.8(4) . . ?
N7 C12 H12 106.7 . . ?
C14 C12 H12 106.7 . . ?
C13 C12 H12 106.7 . . ?
N4 C9 C11 111.1(4) . . ?
N4 C9 C10 111.8(4) . . ?
C11 C9 C10 113.5(4) . . ?
N4 C9 H9 106.6 . . ?
C11 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
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 C8 2.019(4) . ?
Ga1 Cl3 2.2138(13) . ?
Ga1 Cl2 2.2165(13) . ?
Ga1 H3 1.51(8) . ?
N4 C8 1.355(6) . ?
N4 C5 1.386(5) . ?
N4 C9 1.491(5) . ?
N7 C8 1.360(6) . ?
N7 C6 1.386(5) . ?
N7 C12 1.491(5) . ?
C6 C5 1.360(7) . ?
C6 C15 1.493(6) . ?
C5 C16 1.498(6) . ?
C12 C14 1.515(8) . ?
C12 C13 1.521(7) . ?
C12 H12 0.9800 . ?
C9 C11 1.521(6) . ?
C9 C10 1.525(7) . ?
C9 H9 0.9800 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
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
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N4 C8 N7 -1.1(4) . . . . ?
C9 N4 C8 N7 176.0(4) . . . . ?
C5 N4 C8 Ga1 177.2(3) . . . . ?
C9 N4 C8 Ga1 -5.7(6) . . . . ?
C6 N7 C8 N4 1.0(4) . . . . ?
C12 N7 C8 N4 179.0(4) . . . . ?
C6 N7 C8 Ga1 -177.3(3) . . . . ?
C12 N7 C8 Ga1 0.7(6) . . . . ?
C8 N7 C6 C5 -0.5(5) . . . . ?
C12 N7 C6 C5 -178.6(4) . . . . ?
C8 N7 C6 C15 180.0(4) . . . . ?
C12 N7 C6 C15 1.9(6) . . . . ?
N7 C6 C5 N4 -0.2(5) . . . . ?
C15 C6 C5 N4 179.3(4) . . . . ?
N7 C6 C5 C16 177.6(4) . . . . ?
C15 C6 C5 C16 -2.9(8) . . . . ?
C8 N4 C5 C6 0.8(5) . . . . ?
C9 N4 C5 C6 -176.1(4) . . . . ?
C8 N4 C5 C16 -177.1(4) . . . . ?
C9 N4 C5 C16 6.0(7) . . . . ?
C8 N7 C12 C14 -73.4(6) . . . . ?
C6 N7 C12 C14 104.3(5) . . . . ?
C8 N7 C12 C13 54.5(6) . . . . ?
C6 N7 C12 C13 -127.8(4) . . . . ?
C8 N4 C9 C11 -112.6(4) . . . . ?
C5 N4 C9 C11 64.0(5) . . . . ?
C8 N4 C9 C10 119.4(4) . . . . ?
C5 N4 C9 C10 -64.0(5) . . . . ?
