#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:45:22 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179392 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/89/4328948.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_4328948
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            'C31 H49 Ga N2'
_chemical_formula_weight         519.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 111.818(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.6849(12)
_cell_length_b                   10.1700(7)
_cell_length_c                   16.8763(11)
_cell_measurement_reflns_used    9093
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      30.46
_cell_measurement_theta_min      2.32
_cell_volume                     2977.2(3)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            57662
_diffrn_reflns_theta_full        29.57
_diffrn_reflns_theta_max         29.57
_diffrn_reflns_theta_min         2.32
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.7649
_exptl_absorpt_correction_T_min  0.5922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker, SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.30
_refine_diff_density_max         1.350
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         8333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0566
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+7.1160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1606
_refine_ls_wR_factor_ref         0.1637
_reflns_number_gt                7451
_reflns_number_total             8333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic202583w_si_002_13.cif
_cod_data_source_block           14
_cod_database_code               4328948
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.309216(18) 0.86019(3) 0.50267(2) 0.02691(10) Uani 1 1 d .
N1 N 0.27377(13) 0.8235(2) 0.59366(14) 0.0226(4) Uani 1 1 d .
N2 N 0.24165(13) 1.0252(2) 0.49220(14) 0.0237(4) Uani 1 1 d .
C1 C 0.27391(16) 0.7001(3) 0.63411(17) 0.0247(5) Uani 1 1 d .
C2 C 0.34073(19) 0.6525(3) 0.69841(19) 0.0306(6) Uani 1 1 d .
C3 C 0.3373(2) 0.5355(3) 0.7402(2) 0.0382(7) Uani 1 1 d .
H3A H 0.3820 0.5042 0.7837 0.046 Uiso 1 1 calc R
C4 C 0.2699(2) 0.4650(3) 0.7191(2) 0.0398(7) Uani 1 1 d .
H4A H 0.2679 0.3888 0.7497 0.048 Uiso 1 1 calc R
C5 C 0.2053(2) 0.5078(3) 0.6525(2) 0.0367(7) Uani 1 1 d .
H5A H 0.1596 0.4582 0.6366 0.044 Uiso 1 1 calc R
C6 C 0.20627(17) 0.6226(3) 0.60828(19) 0.0287(6) Uani 1 1 d .
C7 C 0.41801(18) 0.7201(4) 0.7224(2) 0.0403(7) Uani 1 1 d .
H7A H 0.4091 0.8058 0.6925 0.048 Uiso 1 1 calc R
C8 C 0.4723(3) 0.6401(5) 0.6914(4) 0.0673(14) Uani 1 1 d .
H8A H 0.4473 0.6234 0.6307 0.101 Uiso 1 1 calc R
H8B H 0.4843 0.5571 0.7219 0.101 Uiso 1 1 calc R
H8C H 0.5194 0.6892 0.7021 0.101 Uiso 1 1 calc R
C9 C 0.4565(3) 0.7475(5) 0.8182(3) 0.0707(15) Uani 1 1 d .
H9A H 0.4217 0.7981 0.8370 0.106 Uiso 1 1 calc R
H9B H 0.5036 0.7970 0.8291 0.106 Uiso 1 1 calc R
H9C H 0.4686 0.6649 0.8490 0.106 Uiso 1 1 calc R
C10 C 0.13472(18) 0.6574(3) 0.5313(2) 0.0359(7) Uani 1 1 d .
H10A H 0.1430 0.7451 0.5107 0.043 Uiso 1 1 calc R
C11 C 0.0612(2) 0.6639(4) 0.5509(3) 0.0517(10) Uani 1 1 d .
H11A H 0.0682 0.7264 0.5965 0.078 Uiso 1 1 calc R
H11B H 0.0502 0.5777 0.5682 0.078 Uiso 1 1 calc R
H11C H 0.0184 0.6917 0.5002 0.078 Uiso 1 1 calc R
C12 C 0.1231(2) 0.5590(4) 0.4595(3) 0.0516(9) Uani 1 1 d .
H12A H 0.1696 0.5545 0.4467 0.077 Uiso 1 1 calc R
H12B H 0.0803 0.5869 0.4090 0.077 Uiso 1 1 calc R
H12C H 0.1122 0.4729 0.4770 0.077 Uiso 1 1 calc R
C13 C 0.21166(15) 1.1131(3) 0.42076(17) 0.0250(5) Uani 1 1 d .
C14 C 0.14025(16) 1.0807(3) 0.3570(2) 0.0318(6) Uani 1 1 d .
C15 C 0.10868(18) 1.1683(4) 0.2902(2) 0.0400(7) Uani 1 1 d .
H15A H 0.0610 1.1485 0.2469 0.048 Uiso 1 1 calc R
C16 C 0.14543(19) 1.2837(4) 0.2858(2) 0.0406(8) Uani 1 1 d .
H16A H 0.1222 1.3429 0.2408 0.049 Uiso 1 1 calc R
C17 C 0.21676(19) 1.3124(3) 0.3478(2) 0.0348(6) Uani 1 1 d .
H17A H 0.2419 1.3908 0.3440 0.042 Uiso 1 1 calc R
C18 C 0.25185(16) 1.2264(3) 0.41595(18) 0.0265(5) Uani 1 1 d .
C19 C 0.33074(18) 1.2597(3) 0.4807(2) 0.0330(6) Uani 1 1 d .
H19A H 0.3465 1.1883 0.5236 0.040 Uiso 1 1 calc R
C20 C 0.3899(2) 1.2675(5) 0.4382(3) 0.0579(11) Uani 1 1 d .
H20A H 0.3899 1.1856 0.4088 0.087 Uiso 1 1 calc R
H20B H 0.4407 1.2824 0.4813 0.087 Uiso 1 1 calc R
H20C H 0.3767 1.3394 0.3975 0.087 Uiso 1 1 calc R
C21 C 0.3307(3) 1.3878(4) 0.5270(3) 0.0629(12) Uani 1 1 d .
H21A H 0.2931 1.3827 0.5539 0.094 Uiso 1 1 calc R
H21B H 0.3175 1.4598 0.4864 0.094 Uiso 1 1 calc R
H21C H 0.3815 1.4027 0.5702 0.094 Uiso 1 1 calc R
C22 C 0.09763(19) 0.9554(4) 0.3603(2) 0.0403(7) Uani 1 1 d .
H22A H 0.1332 0.8989 0.4057 0.048 Uiso 1 1 calc R
C23 C 0.0277(2) 0.9828(6) 0.3830(3) 0.0633(13) Uani 1 1 d .
H23A H 0.0435 1.0307 0.4365 0.095 Uiso 1 1 calc R
H23B H 0.0041 0.9003 0.3888 0.095 Uiso 1 1 calc R
H23C H -0.0092 1.0350 0.3382 0.095 Uiso 1 1 calc R
C24 C 0.0741(3) 0.8794(5) 0.2758(3) 0.0590(11) Uani 1 1 d .
H24A H 0.1194 0.8627 0.2622 0.088 Uiso 1 1 calc R
H24B H 0.0373 0.9310 0.2305 0.088 Uiso 1 1 calc R
H24C H 0.0507 0.7964 0.2812 0.088 Uiso 1 1 calc R
C25 C 0.22546(18) 1.0435(3) 0.55963(19) 0.0293(6) Uani 1 1 d .
C26 C 0.25210(17) 0.9398(3) 0.62845(18) 0.0278(5) Uani 1 1 d .
C27 C 0.1936(3) 0.9167(4) 0.6697(3) 0.0469(9) Uani 1 1 d .
H27A H 0.1482 0.8746 0.6290 0.070 Uiso 1 1 calc R
H27B H 0.1791 1.0003 0.6872 0.070 Uiso 1 1 calc R
H27C H 0.2159 0.8605 0.7192 0.070 Uiso 1 1 calc R
C28 C 0.3226(3) 1.0082(4) 0.7002(3) 0.0536(10) Uani 1 1 d .
H28A H 0.3628 1.0261 0.6783 0.080 Uiso 1 1 calc R
H28B H 0.3425 0.9504 0.7492 0.080 Uiso 1 1 calc R
H28C H 0.3057 1.0901 0.7171 0.080 Uiso 1 1 calc R
C29 C 0.1800(2) 1.1581(4) 0.5696(2) 0.0444(8) Uani 1 1 d .
H29B H 0.1675 1.2149 0.5201 0.067 Uiso 1 1 calc R
H29C H 0.2100 1.2068 0.6205 0.067 Uiso 1 1 calc R
H29D H 0.1327 1.1272 0.5747 0.067 Uiso 1 1 calc R
C30 C 0.2710(2) 0.7495(4) 0.4002(2) 0.0443(8) Uani 1 1 d .
H30B H 0.3044 0.6735 0.4079 0.066 Uiso 1 1 calc R
H30C H 0.2708 0.7997 0.3512 0.066 Uiso 1 1 calc R
H30D H 0.2191 0.7204 0.3907 0.066 Uiso 1 1 calc R
C31 C 0.4165(2) 0.9212(4) 0.5350(3) 0.0476(9) Uani 1 1 d .
H31B H 0.4500 0.8462 0.5405 0.071 Uiso 1 1 calc R
H31C H 0.4321 0.9676 0.5890 0.071 Uiso 1 1 calc R
H31D H 0.4200 0.9800 0.4913 0.071 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'
N N 0.0061 0.0033 '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
N1 Ga1 C30 118.22(13)
N1 Ga1 C31 117.19(15)
C30 Ga1 C31 115.05(18)
N1 Ga1 N2 81.08(9)
C30 Ga1 N2 112.33(14)
C31 Ga1 N2 107.09(14)
C1 N1 C26 118.5(2)
C1 N1 Ga1 127.78(18)
C26 N1 Ga1 113.46(17)
C25 N2 C13 120.2(2)
C25 N2 Ga1 112.09(19)
C13 N2 Ga1 127.74(18)
C2 C1 C6 118.9(3)
C2 C1 N1 121.1(3)
C6 C1 N1 120.0(2)
C3 C2 C1 119.3(3)
C3 C2 C7 118.1(3)
C1 C2 C7 122.5(3)
C4 C3 C2 121.5(3)
C3 C4 C5 119.1(3)
C4 C5 C6 121.4(3)
C5 C6 C1 119.5(3)
C5 C6 C10 118.1(3)
C1 C6 C10 122.4(3)
C2 C7 C9 113.1(3)
C2 C7 C8 110.7(3)
C9 C7 C8 110.2(4)
C6 C10 C12 110.3(3)
C6 C10 C11 113.6(3)
C12 C10 C11 109.1(3)
C18 C13 C14 121.8(3)
C18 C13 N2 120.8(2)
C14 C13 N2 117.3(3)
C15 C14 C13 117.9(3)
C15 C14 C22 120.0(3)
C13 C14 C22 122.1(3)
C16 C15 C14 121.5(3)
C15 C16 C17 119.9(3)
C16 C17 C18 121.0(3)
C13 C18 C17 117.8(3)
C13 C18 C19 123.0(2)
C17 C18 C19 119.2(3)
C18 C19 C21 112.1(3)
C18 C19 C20 110.7(3)
C21 C19 C20 109.6(4)
C14 C22 C23 111.6(3)
C14 C22 C24 111.2(3)
C23 C22 C24 110.5(3)
N2 C25 C29 122.8(3)
N2 C25 C26 117.3(2)
C29 C25 C26 119.9(3)
N1 C26 C25 108.7(2)
N1 C26 C27 114.7(3)
C25 C26 C27 111.9(3)
N1 C26 C28 113.1(3)
C25 C26 C28 103.0(3)
C27 C26 C28 104.7(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Ga1 N1 1.921(2)
Ga1 C30 1.963(3)
Ga1 C31 1.971(3)
Ga1 N2 2.068(2)
N1 C1 1.428(3)
N1 C26 1.444(4)
N2 C25 1.295(4)
N2 C13 1.437(3)
C1 C2 1.401(4)
C1 C6 1.414(4)
C2 C3 1.397(4)
C2 C7 1.512(5)
C3 C4 1.376(5)
C4 C5 1.379(5)
C5 C6 1.389(4)
C6 C10 1.520(4)
C7 C9 1.531(6)
C7 C8 1.535(6)
C10 C12 1.524(5)
C10 C11 1.530(5)
C13 C18 1.394(4)
C13 C14 1.407(4)
C14 C15 1.385(4)
C14 C22 1.515(5)
C15 C16 1.375(5)
C16 C17 1.386(5)
C17 C18 1.399(4)
C18 C19 1.511(4)
C19 C21 1.519(5)
C19 C20 1.528(5)
C22 C23 1.519(5)
C22 C24 1.536(6)
C25 C29 1.488(4)
C25 C26 1.509(4)
C26 C27 1.517(4)
C26 C28 1.580(5)
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
C30 Ga1 N1 C1 51.1(3)
C31 Ga1 N1 C1 -93.5(3)
N2 Ga1 N1 C1 161.8(2)
C30 Ga1 N1 C26 -135.4(2)
C31 Ga1 N1 C26 79.9(2)
N2 Ga1 N1 C26 -24.75(19)
N1 Ga1 N2 C25 16.3(2)
C30 Ga1 N2 C25 133.2(2)
C31 Ga1 N2 C25 -99.5(2)
N1 Ga1 N2 C13 -162.1(2)
C30 Ga1 N2 C13 -45.2(3)
C31 Ga1 N2 C13 82.1(3)
C26 N1 C1 C2 -92.0(3)
Ga1 N1 C1 C2 81.2(3)
C26 N1 C1 C6 89.3(3)
Ga1 N1 C1 C6 -97.5(3)
C6 C1 C2 C3 -5.3(4)
N1 C1 C2 C3 175.9(3)
C6 C1 C2 C7 172.1(3)
N1 C1 C2 C7 -6.6(4)
C1 C2 C3 C4 0.6(5)
C7 C2 C3 C4 -176.9(3)
C2 C3 C4 C5 3.1(5)
C3 C4 C5 C6 -2.2(5)
C4 C5 C6 C1 -2.5(5)
C4 C5 C6 C10 175.3(3)
C2 C1 C6 C5 6.2(4)
N1 C1 C6 C5 -175.0(3)
C2 C1 C6 C10 -171.5(3)
N1 C1 C6 C10 7.3(4)
C3 C2 C7 C9 -54.6(5)
C1 C2 C7 C9 128.0(4)
C3 C2 C7 C8 69.7(4)
C1 C2 C7 C8 -107.7(4)
C5 C6 C10 C12 -67.6(4)
C1 C6 C10 C12 110.1(3)
C5 C6 C10 C11 55.2(4)
C1 C6 C10 C11 -127.1(3)
C25 N2 C13 C18 88.6(3)
Ga1 N2 C13 C18 -93.1(3)
C25 N2 C13 C14 -90.8(3)
Ga1 N2 C13 C14 87.5(3)
C18 C13 C14 C15 -2.9(5)
N2 C13 C14 C15 176.5(3)
C18 C13 C14 C22 177.8(3)
N2 C13 C14 C22 -2.8(4)
C13 C14 C15 C16 0.0(5)
C22 C14 C15 C16 179.2(3)
C14 C15 C16 C17 1.9(6)
C15 C16 C17 C18 -0.9(5)
C14 C13 C18 C17 3.8(4)
N2 C13 C18 C17 -175.5(3)
C14 C13 C18 C19 -176.3(3)
N2 C13 C18 C19 4.4(4)
C16 C17 C18 C13 -1.9(5)
C16 C17 C18 C19 178.2(3)
C13 C18 C19 C21 -118.5(4)
C17 C18 C19 C21 61.4(4)
C13 C18 C19 C20 118.8(3)
C17 C18 C19 C20 -61.4(4)
C15 C14 C22 C23 -72.4(4)
C13 C14 C22 C23 106.8(4)
C15 C14 C22 C24 51.6(5)
C13 C14 C22 C24 -129.2(4)
C13 N2 C25 C29 -3.7(5)
Ga1 N2 C25 C29 177.7(3)
C13 N2 C25 C26 173.9(3)
Ga1 N2 C25 C26 -4.6(3)
C1 N1 C26 C25 -157.6(2)
Ga1 N1 C26 C25 28.2(3)
C1 N1 C26 C27 -31.4(4)
Ga1 N1 C26 C27 154.4(2)
C1 N1 C26 C28 88.6(3)
Ga1 N1 C26 C28 -85.5(3)
N2 C25 C26 N1 -14.6(4)
C29 C25 C26 N1 163.1(3)
N2 C25 C26 C27 -142.4(3)
C29 C25 C26 C27 35.3(4)
N2 C25 C26 C28 105.6(3)
C29 C25 C26 C28 -76.6(4)
