#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:45:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179392 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/89/4328936.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_4328936
loop_
_publ_author_name
'Ana M. Felix'
'Diane A. Dickie'
'Ian S. Horne'
'Giang Page'
'Richard A. Kemp'
_publ_contact_author_address
;Department of Chemistry and Chemical Biology
University of New Mexico
Albuquerque, NM, 87131
;
_publ_contact_author_email       rakemp@unm.edu
_publ_contact_author_name        'Kemp, Richard A.'
_publ_contact_author_phone       1-505-272-7609
_publ_section_title
;
 Addition of Aluminum and Gallium Species to Aromatic and
 Alkyl-Substituted 1,4-Diaza-1,3-butadiene Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              4650
_journal_page_last               4662
_journal_paper_doi               10.1021/ic202583w
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C25 H44 Cl2 Ga2 N2'
_chemical_formula_weight         582.96
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.158(3)
_cell_angle_beta                 92.861(3)
_cell_angle_gamma                91.203(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9899(5)
_cell_length_b                   11.3709(6)
_cell_length_c                   12.9317(6)
_cell_measurement_reflns_used    5301
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      32.77
_cell_measurement_theta_min      1.86
_cell_volume                     1459.30(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      223(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22275
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.46
_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_T_max  0.7357
_exptl_absorpt_correction_T_min  0.4221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Brukers, SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       rod
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         7210
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0253
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0328P)²+0.3808P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0642
_refine_ls_wR_factor_ref         0.0681
_reflns_number_gt                6042
_reflns_number_total             7210
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202583w_si_002_01.cif
_cod_data_source_block           16
_cod_original_cell_volume        1459.30(12)
_cod_database_code               4328936
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.740500(15) 0.404155(15) 0.257353(13) 0.02925(5) Uani 1 1 d .
Ga2 Ga 0.237334(17) 0.175500(17) 0.223185(16) 0.04016(6) Uani 1 1 d .
Cl1 Cl 0.39398(4) 0.16306(4) 0.10761(4) 0.04793(11) Uani 1 1 d .
Cl2 Cl 0.27081(5) 0.00101(5) 0.26130(5) 0.05829(13) Uani 1 1 d .
N1 N 0.71389(11) 0.22325(12) 0.25371(10) 0.0291(3) Uani 1 1 d .
N2 N 0.71581(11) 0.29351(11) 0.08413(10) 0.0271(2) Uani 1 1 d .
C1 C 0.71191(14) 0.19009(14) 0.35228(12) 0.0319(3) Uani 1 1 d .
H1A H 0.7307 0.0975 0.3264 0.038 Uiso 1 1 calc R
C2 C 0.80665(16) 0.27271(18) 0.44493(14) 0.0414(4) Uani 1 1 d .
H2A H 0.7913 0.3649 0.4689 0.050 Uiso 1 1 calc R
H2B H 0.8879 0.2570 0.4151 0.050 Uiso 1 1 calc R
C3 C 0.80211(18) 0.2398(2) 0.54770(16) 0.0517(5) Uani 1 1 d .
H3A H 0.8259 0.1501 0.5253 0.062 Uiso 1 1 calc R
H3B H 0.8606 0.2975 0.6089 0.062 Uiso 1 1 calc R
C4 C 0.67573(19) 0.2547(2) 0.59209(15) 0.0518(5) Uani 1 1 d .
H4A H 0.6745 0.2269 0.6541 0.062 Uiso 1 1 calc R
H4B H 0.6560 0.3466 0.6234 0.062 Uiso 1 1 calc R
C5 C 0.58114(18) 0.1752(2) 0.49880(16) 0.0517(5) Uani 1 1 d .
H5A H 0.5000 0.1913 0.5288 0.062 Uiso 1 1 calc R
H5B H 0.5954 0.0826 0.4736 0.062 Uiso 1 1 calc R
C6 C 0.58551(16) 0.2094(2) 0.39699(16) 0.0461(4) Uani 1 1 d .
H6A H 0.5256 0.1540 0.3361 0.055 Uiso 1 1 calc R
H6B H 0.5646 0.3002 0.4205 0.055 Uiso 1 1 calc R
C7 C 0.72729(13) 0.33543(14) -0.00833(12) 0.0274(3) Uani 1 1 d .
H7A H 0.6838 0.2702 -0.0791 0.033 Uiso 1 1 calc R
C8 C 0.67125(14) 0.46655(15) 0.02289(13) 0.0323(3) Uani 1 1 d .
H8A H 0.7120 0.5316 0.0940 0.039 Uiso 1 1 calc R
H8B H 0.5846 0.4599 0.0353 0.039 Uiso 1 1 calc R
C9 C 0.68503(15) 0.50906(17) -0.07363(14) 0.0377(3) Uani 1 1 d .
H9A H 0.6385 0.4476 -0.1430 0.045 Uiso 1 1 calc R
H9B H 0.6516 0.5950 -0.0517 0.045 Uiso 1 1 calc R
C10 C 0.81820(16) 0.51470(17) -0.09858(15) 0.0408(4) Uani 1 1 d .
H10A H 0.8626 0.5840 -0.0324 0.049 Uiso 1 1 calc R
H10B H 0.8240 0.5357 -0.1643 0.049 Uiso 1 1 calc R
C11 C 0.87685(15) 0.38560(17) -0.12433(14) 0.0386(4) Uani 1 1 d .
H11A H 0.8395 0.3188 -0.1963 0.046 Uiso 1 1 calc R
H11B H 0.9639 0.3946 -0.1341 0.046 Uiso 1 1 calc R
C12 C 0.86194(14) 0.34240(16) -0.02914(13) 0.0336(3) Uani 1 1 d .
H12A H 0.9066 0.4042 0.0413 0.040 Uiso 1 1 calc R
H12B H 0.8959 0.2568 -0.0506 0.040 Uiso 1 1 calc R
C13 C 0.68533(15) 0.17551(15) 0.05876(13) 0.0341(3) Uani 1 1 d .
H13A H 0.6649 0.1156 -0.0173 0.041 Uiso 1 1 calc R
C14 C 0.68352(16) 0.13687(15) 0.15383(13) 0.0354(3) Uani 1 1 d .
H14A H 0.6607 0.0514 0.1410 0.043 Uiso 1 1 calc R
C15 C 0.59063(17) 0.49437(17) 0.30774(15) 0.0434(4) Uani 1 1 d .
H15A H 0.5906 0.5714 0.2933 0.065 Uiso 1 1 calc R
H15B H 0.5857 0.5196 0.3891 0.065 Uiso 1 1 calc R
H15C H 0.5210 0.4370 0.2659 0.065 Uiso 1 1 calc R
C16 C 0.90810(17) 0.4724(2) 0.30117(16) 0.0497(4) Uani 1 1 d .
H16A H 0.9220 0.5426 0.2788 0.075 Uiso 1 1 calc R
H16B H 0.9631 0.4037 0.2631 0.075 Uiso 1 1 calc R
H16C H 0.9228 0.5048 0.3834 0.075 Uiso 1 1 calc R
C17 C 0.08826(19) 0.1363(2) 0.1223(2) 0.0615(5) Uani 1 1 d .
H17A H 0.0187 0.1307 0.1635 0.092 Uiso 1 1 calc R
H17B H 0.0950 0.0540 0.0561 0.092 Uiso 1 1 calc R
H17C H 0.0774 0.2048 0.0972 0.092 Uiso 1 1 calc R
C18 C 0.2633(2) 0.3345(2) 0.36457(19) 0.0636(6) Uani 1 1 d .
H18A H 0.1967 0.3421 0.4131 0.095 Uiso 1 1 calc R
H18B H 0.2666 0.4090 0.3466 0.095 Uiso 1 1 calc R
H18C H 0.3396 0.3313 0.4042 0.095 Uiso 1 1 calc R
C19 C 0.42978(19) 0.2026(2) 0.7972(2) 0.0697(6) Uani 1 1 d .
H19A H 0.4574 0.2809 0.7911 0.105 Uiso 1 1 calc R
H19B H 0.4758 0.1301 0.7485 0.105 Uiso 1 1 calc R
H19C H 0.4422 0.2149 0.8760 0.105 Uiso 1 1 calc R
C20 C 0.29664(17) 0.17476(16) 0.75995(18) 0.0468(4) Uani 1 1 d .
C21 C 0.21531(18) 0.15492(17) 0.83045(17) 0.0476(4) Uani 1 1 d .
H21A H 0.2426 0.1647 0.9038 0.057 Uiso 1 1 calc R
C22 C 0.09414(18) 0.12085(19) 0.7927(2) 0.0555(5) Uani 1 1 d .
H22A H 0.0398 0.1051 0.8398 0.067 Uiso 1 1 calc R
C23 C 0.0530(2) 0.1099(2) 0.6878(2) 0.0637(6) Uani 1 1 d .
H23A H -0.0293 0.0863 0.6627 0.076 Uiso 1 1 calc R
C24 C 0.1306(2) 0.1331(2) 0.6194(2) 0.0663(6) Uani 1 1 d .
H24A H 0.1013 0.1277 0.5479 0.080 Uiso 1 1 calc R
C25 C 0.2516(2) 0.1643(2) 0.65423(19) 0.0582(5) Uani 1 1 d .
H25A H 0.3047 0.1789 0.6057 0.070 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C16 Ga1 C15 128.47(8)
C16 Ga1 N2 111.13(7)
C15 Ga1 N2 107.34(6)
C16 Ga1 N1 112.92(7)
C15 Ga1 N1 106.38(6)
N2 Ga1 N1 79.92(5)
C18 Ga2 C17 122.86(10)
C18 Ga2 Cl2 109.22(8)
C17 Ga2 Cl2 107.91(7)
C18 Ga2 Cl1 108.67(7)
C17 Ga2 Cl1 104.97(8)
Cl2 Ga2 Cl1 100.97(2)
C14 N1 C1 119.68(12)
C14 N1 Ga1 112.34(10)
C1 N1 Ga1 127.52(9)
C13 N2 C7 119.29(12)
C13 N2 Ga1 112.62(10)
C7 N2 Ga1 128.08(9)
N1 C1 C2 110.41(12)
N1 C1 C6 109.21(12)
C2 C1 C6 110.84(14)
C1 C2 C3 110.07(14)
C4 C3 C2 111.47(15)
C5 C4 C3 111.35(15)
C4 C5 C6 111.07(15)
C1 C6 C5 110.15(15)
N2 C7 C8 110.61(11)
N2 C7 C12 108.60(11)
C8 C7 C12 110.93(12)
C7 C8 C9 109.87(12)
C10 C9 C8 111.01(13)
C9 C10 C11 111.33(13)
C12 C11 C10 111.85(13)
C11 C12 C7 109.88(12)
N2 C13 C14 117.00(13)
N1 C14 C13 117.50(13)
C25 C20 C21 118.06(18)
C25 C20 C19 121.7(2)
C21 C20 C19 120.2(2)
C22 C21 C20 120.02(19)
C23 C22 C21 120.4(2)
C24 C23 C22 120.2(2)
C23 C24 C25 120.2(2)
C24 C25 C20 121.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ga1 C16 1.9436(17)
Ga1 C15 1.9492(17)
Ga1 N2 2.0501(12)
Ga1 N1 2.0519(12)
Ga2 C18 1.9514(19)
Ga2 C17 1.9615(19)
Ga2 Cl2 2.2714(5)
Ga2 Cl1 2.3032(5)
N1 C14 1.2685(19)
N1 C1 1.4759(18)
N2 C13 1.2712(19)
N2 C7 1.4731(17)
C1 C2 1.510(2)
C1 C6 1.516(2)
C2 C3 1.529(2)
C3 C4 1.515(3)
C4 C5 1.504(3)
C5 C6 1.526(2)
C7 C8 1.522(2)
C7 C12 1.524(2)
C8 C9 1.531(2)
C9 C10 1.520(2)
C10 C11 1.525(2)
C11 C12 1.521(2)
C13 C14 1.472(2)
C19 C20 1.501(3)
C20 C25 1.386(3)
C20 C21 1.389(3)
C21 C22 1.384(3)
C22 C23 1.361(3)
C23 C24 1.358(3)
C24 C25 1.372(3)
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
C16 Ga1 N1 C14 -115.66(12)
C15 Ga1 N1 C14 98.42(12)
N2 Ga1 N1 C14 -6.85(11)
C16 Ga1 N1 C1 72.25(14)
C15 Ga1 N1 C1 -73.67(13)
N2 Ga1 N1 C1 -178.94(13)
C16 Ga1 N2 C13 117.21(12)
C15 Ga1 N2 C13 -97.76(12)
N1 Ga1 N2 C13 6.40(11)
C16 Ga1 N2 C7 -63.85(13)
C15 Ga1 N2 C7 81.18(12)
N1 Ga1 N2 C7 -174.66(12)
C14 N1 C1 C2 150.40(15)
Ga1 N1 C1 C2 -38.03(17)
C14 N1 C1 C6 -87.48(18)
Ga1 N1 C1 C6 84.09(15)
N1 C1 C2 C3 178.78(14)
C6 C1 C2 C3 57.63(19)
C1 C2 C3 C4 -55.8(2)
C2 C3 C4 C5 55.0(2)
C3 C4 C5 C6 -55.4(2)
N1 C1 C6 C5 179.81(14)
C2 C1 C6 C5 -58.34(19)
C4 C5 C6 C1 56.9(2)
C13 N2 C7 C8 137.54(14)
Ga1 N2 C7 C8 -41.34(16)
C13 N2 C7 C12 -100.51(16)
Ga1 N2 C7 C12 80.62(14)
N2 C7 C8 C9 179.49(12)
C12 C7 C8 C9 58.91(16)
C7 C8 C9 C10 -56.91(17)
C8 C9 C10 C11 54.79(19)
C9 C10 C11 C12 -54.54(19)
C10 C11 C12 C7 55.73(18)
N2 C7 C12 C11 -179.96(12)
C8 C7 C12 C11 -58.20(17)
C7 N2 C13 C14 175.87(13)
Ga1 N2 C13 C14 -5.09(18)
C1 N1 C14 C13 179.11(14)
Ga1 N1 C14 C13 6.33(19)
N2 C13 C14 N1 -0.9(2)
C25 C20 C21 C22 2.5(3)
C19 C20 C21 C22 -175.75(17)
C20 C21 C22 C23 -1.8(3)
C21 C22 C23 C24 -0.3(3)
C22 C23 C24 C25 1.7(3)
C23 C24 C25 C20 -0.9(3)
C21 C20 C25 C24 -1.1(3)
C19 C20 C25 C24 177.04(19)
