#------------------------------------------------------------------------------
#$Date: 2016-11-06 03:59:09 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187944 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/66/4086693.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_4086693
loop_
_publ_author_name
'Cybularczyk, Martyna'
'Dranka, Maciej'
'Zachara, Janusz'
'Horeglad, Paweł'
_publ_section_title
;
 Effect of In--CNHCBonds on the Synthesis, Structure, and Reactivity of
 Dialkylindium Alkoxides: How Indium Compares to Gallium
;
_journal_issue                   19
_journal_name_full               Organometallics
_journal_page_first              3311
_journal_paper_doi               10.1021/acs.organomet.6b00510
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C24 H33 In N2'
_chemical_formula_sum            'C24 H33 In N2'
_chemical_formula_weight         464.34
_chemical_properties_physical    air-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      62
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-25
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.1071(6)
_cell_length_b                   12.2839(4)
_cell_length_c                   8.1899(2)
_cell_measurement_reflns_used    6284
_cell_measurement_temperature    120.0
_cell_measurement_theta_max      30.7230
_cell_measurement_theta_min      3.9550
_cell_volume                     2324.66(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -23.00    5.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8721   91.0000   61.0000 28

  2 omega  -61.00   41.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8721  -38.0000  -90.0000 102

  3 omega  -41.00   29.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       14.8721  -57.0000 -150.0000 70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0020380000
_diffrn_orient_matrix_UB_12      0.0526601000
_diffrn_orient_matrix_UB_13      -0.0350961000
_diffrn_orient_matrix_UB_21      0.0291129000
_diffrn_orient_matrix_UB_22      0.0039132000
_diffrn_orient_matrix_UB_23      0.0267735000
_diffrn_orient_matrix_UB_31      0.0094872000
_diffrn_orient_matrix_UB_32      -0.0233990000
_diffrn_orient_matrix_UB_33      -0.0745153000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10118
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.317
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.027
_exptl_absorpt_correction_T_max  0.782
_exptl_absorpt_correction_T_min  0.736
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_description       irregular
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.4946
_exptl_crystal_size_mid          0.4099
_exptl_crystal_size_min          0.2902
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.00229(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0237
_refine_ls_R_factor_gt           0.0209
_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)+(0.0220P)²+0.9840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0491
_refine_ls_wR_factor_ref         0.0504
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2298
_reflns_number_total             2494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00510_si_002.cif
_cod_data_source_block           md333_ph_mc44
_cod_depositor_comments
'Adding full bibliography for 4086693--4086698.cif.'
_cod_database_code               4086693
_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_shelxl_version_number     2014/7
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
In1 In 0.40313(2) 0.2500 0.70303(2) 0.01795(7) Uani 1 2 d S T P . .
N1 N 0.29127(8) 0.2500 0.4523(2) 0.0152(4) Uani 1 2 d S T P . .
N2 N 0.36795(9) 0.2500 0.3070(2) 0.0172(4) Uani 1 2 d S T P . .
C1 C 0.35005(9) 0.2500 0.4644(3) 0.0145(5) Uani 1 2 d S T P . .
C2 C 0.27355(11) 0.2500 0.2906(3) 0.0219(5) Uani 1 2 d S T P . .
H2 H 0.2348 0.2500 0.2518 0.026 Uiso 1 2 calc RS T P . .
C3 C 0.32172(11) 0.2500 0.1996(3) 0.0219(5) Uani 1 2 d S T P . .
H3 H 0.3237 0.2500 0.0838 0.026 Uiso 1 2 calc RS T P . .
C4 C 0.49392(11) 0.2500 0.6314(4) 0.0323(6) Uani 1 2 d S T P . .
H4A H 0.5004 0.1935 0.5490 0.048 Uiso 0.5 1 calc GR . . A -1
H4B H 0.5181 0.2353 0.7272 0.048 Uiso 0.5 1 calc GR . . A -1
H4C H 0.5041 0.3212 0.5858 0.048 Uiso 0.5 1 calc GR . . A -1
C5 C 0.37663(9) 0.40161(16) 0.8222(2) 0.0290(4) Uani 1 1 d . . . . .
H5A H 0.3807 0.4623 0.7454 0.043 Uiso 1 1 calc GR . . . .
H5B H 0.4011 0.4146 0.9179 0.043 Uiso 1 1 calc GR . . . .
H5C H 0.3361 0.3958 0.8567 0.043 Uiso 1 1 calc GR . . . .
C7 C 0.42775(10) 0.2500 0.2532(3) 0.0172(5) Uani 1 2 d S T P . .
C8 C 0.45497(8) 0.34937(15) 0.2265(2) 0.0211(4) Uani 1 1 d . . . . .
C9 C 0.51114(8) 0.34712(16) 0.1644(2) 0.0263(4) Uani 1 1 d . . . . .
H9 H 0.5307 0.4139 0.1444 0.032 Uiso 1 1 calc R . . . .
C10 C 0.53915(11) 0.2500 0.1313(3) 0.0273(6) Uani 1 2 d S T P . .
C13 C 0.42559(9) 0.45554(16) 0.2666(3) 0.0322(4) Uani 1 1 d . . . . .
H13A H 0.3886 0.4598 0.2085 0.048 Uiso 1 1 calc GR . . . .
H13B H 0.4504 0.5162 0.2329 0.048 Uiso 1 1 calc GR . . . .
H13C H 0.4187 0.4597 0.3845 0.048 Uiso 1 1 calc GR . . . .
C14 C 0.59951(11) 0.2500 0.0575(4) 0.0417(8) Uani 1 2 d S T P . .
H14A H 0.5970 0.2668 -0.0593 0.063 Uiso 0.5 1 calc GR . . B -1
H14B H 0.6171 0.1781 0.0720 0.063 Uiso 0.5 1 calc GR . . B -1
H14C H 0.6233 0.3051 0.1121 0.063 Uiso 0.5 1 calc GR . . B -1
C16 C 0.25260(9) 0.2500 0.5907(3) 0.0144(5) Uani 1 2 d S T P . .
C17 C 0.23443(7) 0.15078(14) 0.6544(2) 0.0199(4) Uani 1 1 d . . . . .
C18 C 0.19870(8) 0.15350(17) 0.7907(2) 0.0267(4) Uani 1 1 d . . . . .
H18 H 0.1859 0.0866 0.8365 0.032 Uiso 1 1 calc R . . . .
C19 C 0.18101(10) 0.2500 0.8623(3) 0.0281(6) Uani 1 2 d S T P . .
C22 C 0.25215(9) 0.04520(15) 0.5777(2) 0.0319(4) Uani 1 1 d . . . . .
H22A H 0.2353 0.0398 0.4682 0.048 Uiso 1 1 calc GR . . . .
H22B H 0.2383 -0.0155 0.6450 0.048 Uiso 1 1 calc GR . . . .
H22C H 0.2944 0.0422 0.5697 0.048 Uiso 1 1 calc GR . . . .
C23 C 0.14248(12) 0.2500 1.0112(3) 0.0496(10) Uani 1 2 d S T P . .
H23A H 0.1025 0.2356 0.9781 0.074 Uiso 0.5 1 calc GR . . C -1
H23B H 0.1446 0.3211 1.0650 0.074 Uiso 0.5 1 calc GR . . C -1
H23C H 0.1554 0.1933 1.0871 0.074 Uiso 0.5 1 calc GR . . C -1
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'
In In -0.7276 1.3100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
37 12 0 0.1737
23 0 -13 0.1832
-23 0 -13 0.1782
-37 12 0 0.1752
0 20 8 0.2285
37 -12 0 0.1747
0 -20 -8 0.2147
-37 -12 0 0.1762
-23 0 13 0.1725
23 0 13 0.1724
0 20 -8 0.1388
0 -20 8 0.1514
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
C4 In1 C1 106.49(9) . .
C4 In1 C5 112.92(6) . .
C4 In1 C5 112.92(6) . 7_565
C5 In1 C1 103.23(6) 7_565 .
C5 In1 C1 103.23(6) . .
C5 In1 C5 116.50(11) . 7_565
C1 N1 C2 111.33(19) . .
C1 N1 C16 124.10(18) . .
C2 N1 C16 124.57(19) . .
C1 N2 C3 111.7(2) . .
C1 N2 C7 125.4(2) . .
C3 N2 C7 122.88(19) . .
N1 C1 In1 126.27(15) . .
N2 C1 In1 130.11(16) . .
N2 C1 N1 103.62(19) . .
N1 C2 H2 126.7 . .
C3 C2 N1 106.6(2) . .
C3 C2 H2 126.7 . .
N2 C3 H3 126.6 . .
C2 C3 N2 106.8(2) . .
C2 C3 H3 126.6 . .
In1 C4 H4A 109.5 . .
In1 C4 H4B 109.5 . .
In1 C4 H4C 109.5 . .
H4A C4 H4B 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
In1 C5 H5A 109.5 . .
In1 C5 H5B 109.5 . .
In1 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C8 C7 N2 118.61(12) . .
C8 C7 N2 118.61(12) 7_565 .
C8 C7 C8 122.8(2) . 7_565
C7 C8 C9 117.46(18) . .
C7 C8 C13 121.45(17) . .
C9 C8 C13 121.07(17) . .
C8 C9 H9 119.2 . .
C10 C9 C8 121.59(18) . .
C10 C9 H9 119.2 . .
C9 C10 C9 119.1(2) . 7_565
C9 C10 C14 120.46(12) 7_565 .
C9 C10 C14 120.46(12) . .
C8 C13 H13A 109.5 . .
C8 C13 H13B 109.5 . .
C8 C13 H13C 109.5 . .
H13A C13 H13B 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14B 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C17 C16 N1 118.79(11) 7_565 .
C17 C16 N1 118.79(11) . .
C17 C16 C17 122.4(2) . 7_565
C16 C17 C22 121.25(16) . .
C18 C17 C16 117.39(17) . .
C18 C17 C22 121.36(16) . .
C17 C18 H18 118.8 . .
C19 C18 C17 122.45(18) . .
C19 C18 H18 118.8 . .
C18 C19 C18 117.8(2) 7_565 .
C18 C19 C23 121.08(12) 7_565 .
C18 C19 C23 121.08(12) . .
C17 C22 H22A 109.5 . .
C17 C22 H22B 109.5 . .
C17 C22 H22C 109.5 . .
H22A C22 H22B 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C19 C23 H23A 109.5 . .
C19 C23 H23B 109.5 . .
C19 C23 H23C 109.5 . .
H23A C23 H23B 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
In1 C1 2.307(2) .
In1 C4 2.178(3) .
In1 C5 2.1901(19) .
In1 C5 2.1902(19) 7_565
N1 C1 1.362(3) .
N1 C2 1.386(3) .
N1 C16 1.443(3) .
N2 C1 1.354(3) .
N2 C3 1.383(3) .
N2 C7 1.450(3) .
C2 H2 0.9500 .
C2 C3 1.339(4) .
C3 H3 0.9500 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C7 C8 1.390(2) .
C7 C8 1.391(2) 7_565
C8 C9 1.394(3) .
C8 C13 1.507(3) .
C9 H9 0.9500 .
C9 C10 1.384(2) .
C10 C9 1.384(2) 7_565
C10 C14 1.520(3) .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
C16 C17 1.391(2) .
C16 C17 1.391(2) 7_565
C17 C18 1.389(2) .
C17 C22 1.498(3) .
C18 H18 0.9500 .
C18 C19 1.384(2) .
C19 C18 1.384(2) 7_565
C19 C23 1.509(4) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 H23A 0.9800 .
C23 H23B 0.9800 .
C23 H23C 0.9800 .
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_4
N1 C2 C3 N2 0.000(0) . .
N1 C16 C17 C18 178.02(17) . .
N1 C16 C17 C22 -2.7(3) . .
N2 C7 C8 C9 -175.79(18) . .
N2 C7 C8 C13 5.6(3) . .
C1 N1 C2 C3 0.000(0) . .
C1 N1 C16 C17 90.31(17) . 7_565
C1 N1 C16 C17 -90.30(17) . .
C1 N2 C3 C2 0.000(0) . .
C1 N2 C7 C8 -90.84(18) . .
C1 N2 C7 C8 90.84(18) . 7_565
C2 N1 C1 In1 180.0 . .
C2 N1 C1 N2 0.000(0) . .
C2 N1 C16 C17 89.70(17) . .
C2 N1 C16 C17 -89.69(17) . 7_565
C3 N2 C1 In1 180.0 . .
C3 N2 C1 N1 0.000(0) . .
C3 N2 C7 C8 89.16(18) . .
C3 N2 C7 C8 -89.16(18) . 7_565
C7 N2 C1 In1 0.000(0) . .
C7 N2 C1 N1 180.000(0) . .
C7 N2 C3 C2 180.000(0) . .
C7 C8 C9 C10 -0.4(3) . .
C8 C7 C8 C9 2.5(3) 7_565 .
C8 C7 C8 C13 -176.12(16) 7_565 .
C8 C9 C10 C9 -1.6(4) . 7_565
C8 C9 C10 C14 177.6(2) . .
C13 C8 C9 C10 178.19(19) . .
C16 N1 C1 In1 0.000(0) . .
C16 N1 C1 N2 180.000(0) . .
C16 N1 C2 C3 180.000(0) . .
C16 C17 C18 C19 0.3(3) . .
C17 C16 C17 C18 -2.6(3) 7_565 .
C17 C16 C17 C22 176.65(14) 7_565 .
C17 C18 C19 C18 1.9(3) . 7_565
C17 C18 C19 C23 -179.6(2) . .
C22 C17 C18 C19 -179.00(19) . .
