#------------------------------------------------------------------------------
#$Date: 2016-03-23 20:26:43 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179412 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/09/4330933.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_4330933
loop_
_publ_author_name
'Chelsea D. Cates'
'Thomas W. Myers'
'Louise A. Berben'
_publ_section_title
;
 (IP)2GaIII Complexes Facilitate Net Two-Electron Redox Transformations
 (IP = α-Iminopyridine)
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11891
_journal_page_last               11897
_journal_paper_doi               10.1021/ic301792w
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C36 H46 Ga N4 O'
_chemical_formula_weight         620.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.169(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.420(3)
_cell_length_b                   9.7005(12)
_cell_length_c                   16.920(2)
_cell_measurement_reflns_used    90
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      29.34
_cell_measurement_theta_min      2.54
_cell_volume                     3232.2(7)
_computing_cell_refinement       'Bruker Saint'
_computing_data_collection       'Bruker Duo'
_computing_data_reduction        'Bruker Saint'
_computing_molecular_graphics    'Bruker Shelxtl'
_computing_publication_material  'Bruker Shelxtl'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0595
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            23440
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.18
_diffrn_reflns_theta_min         2.07
_exptl_absorpt_coefficient_mu    0.885
_exptl_absorpt_correction_T_max  0.9966
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_description       Block
_exptl_crystal_F_000             1316
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         5549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.958
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0356
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0442P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0883
_reflns_number_gt                4243
_reflns_number_total             5549
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301792w_si_002_1.cif
_cod_data_source_block           twm58
_cod_database_code               4330933
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Ga1 Ga 0.5000 0.40013(2) 0.2500 0.01454(7) Uani 1 2 d S
O1 O 0.5000 0.58844(15) 0.2500 0.0277(4) Uani 1 2 d S
H1B H 0.5128 0.6189 0.2146 0.041 Uiso 1 1 d R
N1 N 0.42143(6) 0.30360(12) 0.16429(8) 0.0150(2) Uani 1 1 d .
N2 N 0.53410(6) 0.38104(13) 0.14996(8) 0.0175(2) Uani 1 1 d .
C1 C 0.42672(7) 0.27737(16) 0.08862(10) 0.0196(3) Uani 1 1 d .
H1A H 0.3920 0.2329 0.0442 0.023 Uiso 1 1 calc R
C2 C 0.48650(7) 0.31933(16) 0.07879(10) 0.0194(3) Uani 1 1 d .
C3 C 0.49809(8) 0.30277(19) 0.00240(10) 0.0285(4) Uani 1 1 d .
H3A H 0.4653 0.2613 -0.0456 0.034 Uiso 1 1 calc R
C4 C 0.55769(9) 0.3481(2) -0.00028(12) 0.0339(4) Uani 1 1 d .
H4A H 0.5658 0.3381 -0.0501 0.041 Uiso 1 1 calc R
C5 C 0.60672(8) 0.41014(19) 0.07367(11) 0.0296(4) Uani 1 1 d .
H5A H 0.6478 0.4407 0.0735 0.036 Uiso 1 1 calc R
C6 C 0.59281(8) 0.42464(16) 0.14554(10) 0.0223(3) Uani 1 1 d .
H6A H 0.6252 0.4664 0.1937 0.027 Uiso 1 1 calc R
C7 C 0.35764(7) 0.27385(14) 0.17001(9) 0.0147(3) Uani 1 1 d .
C8 C 0.30124(7) 0.35937(15) 0.12662(9) 0.0147(3) Uani 1 1 d .
C9 C 0.24040(7) 0.33024(16) 0.13537(9) 0.0184(3) Uani 1 1 d .
H9A H 0.2025 0.3850 0.1070 0.022 Uiso 1 1 calc R
C10 C 0.23544(7) 0.22110(17) 0.18560(10) 0.0219(3) Uani 1 1 d .
H10A H 0.1946 0.2039 0.1911 0.026 Uiso 1 1 calc R
C11 C 0.29114(8) 0.13791(16) 0.22745(10) 0.0213(3) Uani 1 1 d .
H11A H 0.2873 0.0645 0.2606 0.026 Uiso 1 1 calc R
C12 C 0.35316(7) 0.16232(15) 0.22074(9) 0.0175(3) Uani 1 1 d .
C13 C 0.30540(7) 0.48369(14) 0.07376(9) 0.0163(3) Uani 1 1 d .
H13A H 0.3436 0.4682 0.0567 0.020 Uiso 1 1 calc R
C14 C 0.31998(10) 0.61570(17) 0.12657(11) 0.0292(4) Uani 1 1 d .
H14A H 0.3231 0.6916 0.0919 0.044 Uiso 1 1 calc R
H14B H 0.3621 0.6063 0.1756 0.044 Uiso 1 1 calc R
H14C H 0.2839 0.6325 0.1456 0.044 Uiso 1 1 calc R
C15 C 0.24176(9) 0.50171(17) -0.00838(10) 0.0255(3) Uani 1 1 d .
H15A H 0.2497 0.5716 -0.0436 0.038 Uiso 1 1 calc R
H15B H 0.2045 0.5287 0.0061 0.038 Uiso 1 1 calc R
H15C H 0.2311 0.4162 -0.0394 0.038 Uiso 1 1 calc R
C16 C 0.41263(8) 0.06448(16) 0.26231(11) 0.0231(3) Uani 1 1 d .
H16A H 0.4544 0.1151 0.2707 0.028 Uiso 1 1 calc R
C17 C 0.40684(10) -0.0553(2) 0.20113(15) 0.0511(6) Uani 1 1 d .
H17A H 0.4434 -0.1189 0.2281 0.077 Uiso 1 1 calc R
H17B H 0.4092 -0.0207 0.1492 0.077 Uiso 1 1 calc R
H17C H 0.3643 -0.1017 0.1877 0.077 Uiso 1 1 calc R
C18 C 0.41858(9) 0.0113(2) 0.35027(14) 0.0427(5) Uani 1 1 d .
H18A H 0.4135 0.0869 0.3839 0.064 Uiso 1 1 calc R
H18B H 0.4623 -0.0306 0.3794 0.064 Uiso 1 1 calc R
H18C H 0.3837 -0.0556 0.3426 0.064 Uiso 1 1 calc R
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'
Ga Ga 0.2307 1.6083 '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'
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 N1 118.34(4) . 2_655
O1 Ga1 N1 118.34(4) . .
N1 Ga1 N1 123.32(7) 2_655 .
O1 Ga1 N2 95.06(3) . .
N1 Ga1 N2 94.82(5) 2_655 .
N1 Ga1 N2 80.34(5) . .
O1 Ga1 N2 95.06(3) . 2_655
N1 Ga1 N2 80.34(5) 2_655 2_655
N1 Ga1 N2 94.82(5) . 2_655
N2 Ga1 N2 169.87(7) . 2_655
Ga1 O1 H1B 111.5 . .
C1 N1 C7 117.51(11) . .
C1 N1 Ga1 114.83(9) . .
C7 N1 Ga1 127.22(9) . .
C6 N2 C2 118.20(13) . .
C6 N2 Ga1 129.88(10) . .
C2 N2 Ga1 111.85(9) . .
N1 C1 C2 118.29(13) . .
N1 C1 H1A 120.9 . .
C2 C1 H1A 120.9 . .
N2 C2 C1 114.63(13) . .
N2 C2 C3 120.90(14) . .
C1 C2 C3 124.46(14) . .
C4 C3 C2 119.62(15) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C3 C4 C5 119.06(15) . .
C3 C4 H4A 120.5 . .
C5 C4 H4A 120.5 . .
C6 C5 C4 119.01(15) . .
C6 C5 H5A 120.5 . .
C4 C5 H5A 120.5 . .
N2 C6 C5 123.20(15) . .
N2 C6 H6A 118.4 . .
C5 C6 H6A 118.4 . .
C12 C7 C8 121.31(13) . .
C12 C7 N1 119.37(12) . .
C8 C7 N1 119.30(12) . .
C9 C8 C7 118.01(13) . .
C9 C8 C13 119.63(12) . .
C7 C8 C13 122.33(12) . .
C10 C9 C8 121.24(14) . .
C10 C9 H9A 119.4 . .
C8 C9 H9A 119.4 . .
C11 C10 C9 120.02(14) . .
C11 C10 H10A 120.0 . .
C9 C10 H10A 120.0 . .
C10 C11 C12 121.06(14) . .
C10 C11 H11A 119.5 . .
C12 C11 H11A 119.5 . .
C11 C12 C7 118.35(13) . .
C11 C12 C16 120.45(13) . .
C7 C12 C16 121.06(13) . .
C14 C13 C8 111.52(13) . .
C14 C13 C15 109.98(13) . .
C8 C13 C15 112.78(12) . .
C14 C13 H13A 107.4 . .
C8 C13 H13A 107.4 . .
C15 C13 H13A 107.4 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C12 C16 C17 109.35(13) . .
C12 C16 C18 113.18(14) . .
C17 C16 C18 110.82(17) . .
C12 C16 H16A 107.8 . .
C17 C16 H16A 107.8 . .
C18 C16 H16A 107.8 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ga1 O1 1.8266(15) .
Ga1 N1 1.9727(12) 2_655
Ga1 N1 1.9728(12) .
Ga1 N2 2.0990(12) .
Ga1 N2 2.0990(12) 2_655
O1 H1B 0.8072 .
N1 C1 1.3532(18) .
N1 C7 1.4366(17) .
N2 C6 1.3565(19) .
N2 C2 1.3717(18) .
C1 C2 1.415(2) .
C1 H1A 0.9300 .
C2 C3 1.418(2) .
C3 C4 1.368(2) .
C3 H3A 0.9300 .
C4 C5 1.413(2) .
C4 H4A 0.9300 .
C5 C6 1.368(2) .
C5 H5A 0.9300 .
C6 H6A 0.9300 .
C7 C12 1.408(2) .
C7 C8 1.4103(19) .
C8 C9 1.3970(19) .
C8 C13 1.525(2) .
C9 C10 1.388(2) .
C9 H9A 0.9300 .
C10 C11 1.382(2) .
C10 H10A 0.9300 .
C11 C12 1.397(2) .
C11 H11A 0.9300 .
C12 C16 1.521(2) .
C13 C14 1.522(2) .
C13 C15 1.526(2) .
C13 H13A 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C17 1.529(3) .
C16 C18 1.532(2) .
C16 H16A 0.9800 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 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
O1 Ga1 N1 C1 89.19(10) .
N1 Ga1 N1 C1 -90.81(10) 2_655
N2 Ga1 N1 C1 -1.38(10) .
N2 Ga1 N1 C1 -172.41(10) 2_655
O1 Ga1 N1 C7 -82.94(12) .
N1 Ga1 N1 C7 97.06(12) 2_655
N2 Ga1 N1 C7 -173.51(12) .
N2 Ga1 N1 C7 15.46(12) 2_655
O1 Ga1 N2 C6 61.19(13) .
N1 Ga1 N2 C6 -57.87(13) 2_655
N1 Ga1 N2 C6 179.11(14) .
N2 Ga1 N2 C6 -118.82(13) 2_655
O1 Ga1 N2 C2 -115.88(10) .
N1 Ga1 N2 C2 125.06(10) 2_655
N1 Ga1 N2 C2 2.05(10) .
N2 Ga1 N2 C2 64.12(10) 2_655
C7 N1 C1 C2 173.45(13) .
Ga1 N1 C1 C2 0.52(18) .
C6 N2 C2 C1 -179.79(13) .
Ga1 N2 C2 C1 -2.35(16) .
C6 N2 C2 C3 -0.6(2) .
Ga1 N2 C2 C3 176.85(12) .
N1 C1 C2 N2 1.3(2) .
N1 C1 C2 C3 -177.84(15) .
N2 C2 C3 C4 0.4(3) .
C1 C2 C3 C4 179.54(17) .
C2 C3 C4 C5 0.3(3) .
C3 C4 C5 C6 -0.8(3) .
C2 N2 C6 C5 0.1(2) .
Ga1 N2 C6 C5 -176.84(12) .
C4 C5 C6 N2 0.6(3) .
C1 N1 C7 C12 109.43(16) .
Ga1 N1 C7 C12 -78.63(16) .
C1 N1 C7 C8 -72.35(17) .
Ga1 N1 C7 C8 99.60(14) .
C12 C7 C8 C9 0.0(2) .
N1 C7 C8 C9 -178.20(12) .
C12 C7 C8 C13 177.88(13) .
N1 C7 C8 C13 -0.3(2) .
C7 C8 C9 C10 0.4(2) .
C13 C8 C9 C10 -177.55(14) .
C8 C9 C10 C11 -0.7(2) .
C9 C10 C11 C12 0.5(2) .
C10 C11 C12 C7 -0.2(2) .
C10 C11 C12 C16 -175.98(15) .
C8 C7 C12 C11 -0.1(2) .
N1 C7 C12 C11 178.07(13) .
C8 C7 C12 C16 175.69(13) .
N1 C7 C12 C16 -6.1(2) .
C9 C8 C13 C14 83.68(17) .
C7 C8 C13 C14 -94.17(17) .
C9 C8 C13 C15 -40.66(19) .
C7 C8 C13 C15 141.49(14) .
C11 C12 C16 C17 85.2(2) .
C7 C12 C16 C17 -90.52(19) .
C11 C12 C16 C18 -38.9(2) .
C7 C12 C16 C18 145.41(15) .
