#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/05/2240525.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2240525
loop_
_publ_author_name
'Zhao, Sheng-Lan'
'Yuan, Jian-Chao'
'Zhao, Yan'
_publ_section_title
;
 Crystal structure of
 2,3-bis[(4-tert-butyl-2,6-dimethylphenyl)imino]butane
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o258
_journal_paper_doi               10.1107/S2056989015005551
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C28 H40 N2'
_chemical_formula_moiety         'C28 H40 N2'
_chemical_formula_sum            'C28 H40 N2'
_chemical_formula_weight         404.62
_chemical_name_common
;
2,3-Bis[(4-tert-butyl-2,6-dimethylphenyl)imino]butane
;
_chemical_name_systematic
4-tert-Butyl-N-{3-[(4-tert-butyl-2,6-dimethylphenyl)imino]butan-2-ylidene}-2,6-dimethylaniline
_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                107.913(9)
_cell_angle_beta                 100.484(10)
_cell_angle_gamma                99.260(9)
_cell_formula_units_Z            1
_cell_length_a                   5.993(6)
_cell_length_b                   10.064(9)
_cell_length_c                   11.614(11)
_cell_measurement_reflns_used    1229
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.35
_cell_volume                     637.5(10)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
APEX2 (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEXII 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  0.0295
_diffrn_reflns_av_sigmaI/netI    0.0633
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4557
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.061
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_correction_T_min  0.9862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             222
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2310
_refine_ls_number_restraints     42
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.1535
_refine_ls_R_factor_gt           0.1024
_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)+(0.0400P)²+1.2419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2204
_reflns_number_gt                1348
_reflns_number_total             2310
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5841sup1.cif
_cod_data_source_block           I
_cod_database_code               2240525
_cod_database_fobs_code          2240525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.4381(7) 0.6834(4) 0.3770(4) 0.0394(10) Uani d . 1 1
C C2 0.2730(7) 0.6166(4) 0.2638(4) 0.0434(11) Uani d . 1 1
C C3 0.2889(7) 0.4854(4) 0.1863(4) 0.0439(11) Uani d . 1 1
H H3 0.1786 0.4407 0.1104 0.053 Uiso calc R 1 1
C C4 0.4620(7) 0.4180(4) 0.2170(4) 0.0413(11) Uani d . 1 1
C C5 0.6199(8) 0.4869(4) 0.3302(4) 0.0466(11) Uani d . 1 1
H H5 0.7373 0.4430 0.3531 0.056 Uiso calc R 1 1
C C6 0.6132(8) 0.6185(4) 0.4121(4) 0.0431(11) Uani d . 1 1
C C7 0.0812(9) 0.6857(5) 0.2255(5) 0.0642(15) Uani d . 1 1
H H7A -0.0024 0.7076 0.2894 0.096 Uiso calc R 1 1
H H7B -0.0239 0.6209 0.1487 0.096 Uiso calc R 1 1
H H7C 0.1475 0.7725 0.2138 0.096 Uiso calc R 1 1
C C8 0.4746(9) 0.2729(4) 0.1263(4) 0.0540(13) Uani d U 1 1
C C9 0.5397(13) 0.2937(6) 0.0139(6) 0.107(2) Uani d U 1 1
H H9A 0.5464 0.2030 -0.0431 0.160 Uiso calc R 1 1
H H9B 0.6895 0.3591 0.0387 0.160 Uiso calc R 1 1
H H9C 0.4250 0.3322 -0.0264 0.160 Uiso calc R 1 1
C C10 0.2528(12) 0.1679(6) 0.0939(8) 0.138(3) Uani d U 1 1
H H10A 0.1292 0.2030 0.0567 0.208 Uiso calc R 1 1
H H10B 0.2225 0.1533 0.1680 0.208 Uiso calc R 1 1
H H10C 0.2614 0.0785 0.0357 0.208 Uiso calc R 1 1
C C11 0.6673(13) 0.2145(6) 0.1849(6) 0.112(2) Uani d U 1 1
H H11A 0.6383 0.2030 0.2603 0.167 Uiso calc R 1 1
H H11B 0.8149 0.2805 0.2039 0.167 Uiso calc R 1 1
H H11C 0.6703 0.1233 0.1274 0.167 Uiso calc R 1 1
C C12 0.7936(9) 0.6874(5) 0.5336(4) 0.0648(15) Uani d . 1 1
H H12A 0.9289 0.7412 0.5211 0.097 Uiso calc R 1 1
H H12B 0.8363 0.6146 0.5645 0.097 Uiso calc R 1 1
H H12C 0.7313 0.7507 0.5930 0.097 Uiso calc R 1 1
C C13 0.5168(8) 0.9330(4) 0.4552(4) 0.0404(10) Uani d . 1 1
C C14 0.6647(10) 0.9478(5) 0.3680(5) 0.0671(16) Uani d . 1 1
H H14A 0.6877 0.8553 0.3238 0.101 Uiso calc R 1 1
H H14B 0.8131 1.0115 0.4145 0.101 Uiso calc R 1 1
H H14C 0.5890 0.9860 0.3095 0.101 Uiso calc R 1 1
N N1 0.4167(6) 0.8151(3) 0.4603(3) 0.0440(10) Uani d . 1 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . 120.6(3)
C2 C1 N1 . 119.1(4)
C6 C1 N1 . 120.2(4)
C1 C2 C3 . 118.6(4)
C1 C2 C7 . 121.0(4)
C3 C2 C7 . 120.4(4)
C4 C3 C2 . 122.6(4)
C4 C3 H3 . 118.7
C2 C3 H3 . 118.7
C5 C4 C3 . 116.9(4)
C5 C4 C8 . 122.5(4)
C3 C4 C8 . 120.6(4)
C4 C5 C6 . 123.2(4)
C4 C5 H5 . 118.4
C6 C5 H5 . 118.4
C1 C6 C5 . 118.0(4)
C1 C6 C12 . 122.0(4)
C5 C6 C12 . 120.0(4)
C2 C7 H7A . 109.5
C2 C7 H7B . 109.5
H7A C7 H7B . 109.5
C2 C7 H7C . 109.5
H7A C7 H7C . 109.5
H7B C7 H7C . 109.5
C10 C8 C9 . 112.2(6)
C10 C8 C11 . 108.4(5)
C9 C8 C11 . 105.7(5)
C10 C8 C4 . 110.2(4)
C9 C8 C4 . 109.4(4)
C11 C8 C4 . 110.9(4)
C8 C9 H9A . 109.5
C8 C9 H9B . 109.5
H9A C9 H9B . 109.5
C8 C9 H9C . 109.5
H9A C9 H9C . 109.5
H9B C9 H9C . 109.5
C8 C10 H10A . 109.5
C8 C10 H10B . 109.5
H10A C10 H10B . 109.5
C8 C10 H10C . 109.5
H10A C10 H10C . 109.5
H10B C10 H10C . 109.5
C8 C11 H11A . 109.5
C8 C11 H11B . 109.5
H11A C11 H11B . 109.5
C8 C11 H11C . 109.5
H11A C11 H11C . 109.5
H11B C11 H11C . 109.5
C6 C12 H12A . 109.5
C6 C12 H12B . 109.5
H12A C12 H12B . 109.5
C6 C12 H12C . 109.5
H12A C12 H12C . 109.5
H12B C12 H12C . 109.5
N1 C13 C14 . 124.9(4)
N1 C13 C13 2_676 116.8(5)
C14 C13 C13 2_676 118.2(5)
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 N1 C1 . 120.1(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.388(6)
C1 C6 . 1.386(6)
C1 N1 . 1.421(5)
C2 C3 . 1.379(5)
C2 C7 . 1.505(6)
C3 C4 . 1.380(6)
C3 H3 . 0.9300
C4 C5 . 1.372(6)
C4 C8 . 1.538(5)
C5 C6 . 1.384(6)
C5 H5 . 0.9300
C6 C12 . 1.497(6)
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
C8 C10 . 1.465(7)
C8 C9 . 1.493(7)
C8 C11 . 1.523(7)
C9 H9A . 0.9600
C9 H9B . 0.9600
C9 H9C . 0.9600
C10 H10A . 0.9600
C10 H10B . 0.9600
C10 H10C . 0.9600
C11 H11A . 0.9600
C11 H11B . 0.9600
C11 H11C . 0.9600
C12 H12A . 0.9600
C12 H12B . 0.9600
C12 H12C . 0.9600
C13 N1 . 1.264(5)
C13 C14 . 1.486(6)
C13 C13 2_676 1.497(7)
C14 H14A . 0.9600
C14 H14B . 0.9600
C14 H14C . 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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . -0.9(6)
N1 C1 C2 C3 . -177.0(4)
C6 C1 C2 C7 . 179.5(4)
N1 C1 C2 C7 . 3.5(6)
C1 C2 C3 C4 . 0.1(6)
C7 C2 C3 C4 . 179.7(4)
C2 C3 C4 C5 . 0.6(6)
C2 C3 C4 C8 . -179.0(4)
C3 C4 C5 C6 . -0.5(6)
C8 C4 C5 C6 . 179.0(4)
C2 C1 C6 C5 . 0.9(6)
N1 C1 C6 C5 . 176.9(4)
C2 C1 C6 C12 . -179.9(4)
N1 C1 C6 C12 . -3.9(6)
C4 C5 C6 C1 . -0.2(6)
C4 C5 C6 C12 . -179.4(4)
C5 C4 C8 C10 . 125.0(6)
C3 C4 C8 C10 . -55.4(7)
C5 C4 C8 C9 . -111.2(5)
C3 C4 C8 C9 . 68.3(6)
C5 C4 C8 C11 . 5.0(6)
C3 C4 C8 C11 . -175.5(5)
C14 C13 N1 C1 . -1.2(7)
C13 C13 N1 C1 2_676 179.2(5)
C2 C1 N1 C13 . -91.4(5)
C6 C1 N1 C13 . 92.6(5)
