#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238967.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_2238967
loop_
_publ_author_name
'Zhao, Jie'
'Yuan, Jianchao'
'Xu, Weibing'
'Chen, Jingjing'
'Mu, Yanqiong'
_publ_section_title
;
 2,3-Bis{[2,3-dimethyl-6-(phenylvinyl)phenyl]imino}butane
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o130
_journal_paper_doi               10.1107/S1600536814000440
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C36 H36 N2'
_chemical_formula_moiety         'C36 H36 N2'
_chemical_formula_sum            'C36 H36 N2'
_chemical_formula_weight         496.67
_chemical_name_systematic
;
2,3-Bis{[2,3-dimethyl-6-(phenylvinyl)phenyl]imino}butane
;
_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                 101.679(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.613(8)
_cell_length_b                   16.285(14)
_cell_length_c                   9.639(8)
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.50
_cell_measurement_theta_min      2.49
_cell_volume                     1478(2)
_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  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10305
_diffrn_reflns_theta_full        25.30
_diffrn_reflns_theta_max         25.30
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_T_max  0.9885
_exptl_absorpt_correction_T_min  0.9835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.116
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.416
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2693
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.1034
_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)+(0.1098P)²+2.2955P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2668
_refine_ls_wR_factor_ref         0.3266
_reflns_number_gt                1374
_reflns_number_total             2693
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            qm2103sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238967
_cod_database_fobs_code          2238967
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_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 0.7542(5) 0.9715(4) 0.3661(7) 0.0873(16) Uani d U 1 1
C C2 0.8434(5) 1.0392(4) 0.3706(5) 0.0738(15) Uani d . 1 1
C C3 0.9406(5) 1.0398(4) 0.2810(6) 0.0795(16) Uani d . 1 1
C C4 0.9452(6) 0.9752(5) 0.1928(7) 0.0954(19) Uani d . 1 1
H H4 1.0072 0.9770 0.1303 0.114 Uiso calc R 1 1
C C5 0.8604(7) 0.9073(5) 0.1938(8) 0.107(2) Uani d . 1 1
H H5 0.8682 0.8633 0.1344 0.128 Uiso calc R 1 1
C C6 0.7627(6) 0.9037(4) 0.2827(9) 0.112(2) Uani d U 1 1
C C7 0.6752(7) 0.8283(4) 0.2878(10) 0.135(2) Uani d U 1 1
C C8 0.7248(9) 0.7605(5) 0.3422(13) 0.175(3) Uani d U 1 1
H H8A 0.8211 0.7558 0.3819 0.210 Uiso calc R 1 1
H H8B 0.6649 0.7157 0.3421 0.210 Uiso calc R 1 1
C C9 0.5196(6) 0.8376(4) 0.2159(9) 0.116(2) Uani d U 1 1
C C10 0.4124(7) 0.8072(4) 0.2744(8) 0.108(2) Uani d . 1 1
H H10 0.4340 0.7810 0.3619 0.130 Uiso calc R 1 1
C C11 0.2722(7) 0.8147(5) 0.2058(9) 0.110(2) Uani d . 1 1
H H11 0.2004 0.7944 0.2481 0.132 Uiso calc R 1 1
C C12 0.2387(7) 0.8512(4) 0.0777(8) 0.101(2) Uani d . 1 1
H H12 0.1442 0.8555 0.0313 0.121 Uiso calc R 1 1
C C13 0.3433(7) 0.8816(5) 0.0169(7) 0.109(2) Uani d . 1 1
H H13 0.3207 0.9069 -0.0713 0.131 Uiso calc R 1 1
C C14 0.4836(7) 0.8750(4) 0.0858(8) 0.107(2) Uani d . 1 1
H H14 0.5547 0.8961 0.0436 0.128 Uiso calc R 1 1
C C15 0.8381(7) 1.1086(4) 0.4719(7) 0.107(2) Uani d . 1 1
H H15A 0.7756 1.1506 0.4254 0.160 Uiso calc R 1 1
H H15B 0.9317 1.1309 0.5026 0.160 Uiso calc R 1 1
H H15C 0.8038 1.0886 0.5524 0.160 Uiso calc R 1 1
C C16 1.0396(6) 1.1122(4) 0.2799(7) 0.109(2) Uani d . 1 1
H H16A 1.0944 1.1040 0.2081 0.163 Uiso calc R 1 1
H H16B 1.1023 1.1168 0.3707 0.163 Uiso calc R 1 1
H H16C 0.9848 1.1617 0.2601 0.163 Uiso calc R 1 1
C C17 0.5439(5) 1.0046(4) 0.4443(6) 0.0981(17) Uani d U 1 1
C C18 0.4816(6) 1.0561(5) 0.3171(7) 0.114(2) Uani d U 1 1
H H18A 0.5390 1.0508 0.2468 0.171 Uiso calc R 1 1
H H18B 0.4794 1.1126 0.3450 0.171 Uiso calc R 1 1
H H18C 0.3868 1.0378 0.2783 0.171 Uiso calc R 1 1
N N1 0.6610(4) 0.9671(3) 0.4649(5) 0.0950(14) Uani d U 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_1
_geom_angle_site_symmetry_3
_geom_angle
C6 C1 C2 . . 123.0(5)
C6 C1 N1 . . 117.7(6)
C2 C1 N1 . . 118.8(7)
C1 C2 C3 . . 118.2(6)
C1 C2 C15 . . 121.0(5)
C3 C2 C15 . . 120.8(6)
C4 C3 C2 . . 119.5(6)
C4 C3 C16 . . 119.8(6)
C2 C3 C16 . . 120.7(6)
C3 C4 C5 . . 121.6(6)
C3 C4 H4 . . 119.2
C5 C4 H4 . . 119.2
C4 C5 C6 . . 120.8(7)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C1 C6 C5 . . 116.8(6)
C1 C6 C7 . . 122.6(8)
C5 C6 C7 . . 120.5(9)
C8 C7 C6 . . 124.0(6)
C8 C7 C9 . . 121.7(7)
C6 C7 C9 . . 114.3(5)
C7 C8 H8A . . 120.0
C7 C8 H8B . . 120.0
H8A C8 H8B . . 120.0
C10 C9 C14 . . 117.8(6)
C10 C9 C7 . . 122.0(7)
C14 C9 C7 . . 120.1(7)
C9 C10 C11 . . 121.0(7)
C9 C10 H10 . . 119.5
C11 C10 H10 . . 119.5
C12 C11 C10 . . 120.4(7)
C12 C11 H11 . . 119.8
C10 C11 H11 . . 119.8
C11 C12 C13 . . 119.7(6)
C11 C12 H12 . . 120.1
C13 C12 H12 . . 120.1
C12 C13 C14 . . 120.0(7)
C12 C13 H13 . . 120.0
C14 C13 H13 . . 120.0
C9 C14 C13 . . 121.0(6)
C9 C14 H14 . . 119.5
C13 C14 H14 . . 119.5
C2 C15 H15A . . 109.5
C2 C15 H15B . . 109.5
H15A C15 H15B . . 109.5
C2 C15 H15C . . 109.5
H15A C15 H15C . . 109.5
H15B C15 H15C . . 109.5
C3 C16 H16A . . 109.5
C3 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
C3 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
N1 C17 C17 . 3_676 116.8(5)
N1 C17 C18 . . 126.4(5)
C17 C17 C18 3_676 . 116.7(5)
C17 C18 H18A . . 109.5
C17 C18 H18B . . 109.5
H18A C18 H18B . . 109.5
C17 C18 H18C . . 109.5
H18A C18 H18C . . 109.5
H18B C18 H18C . . 109.5
C17 N1 C1 . . 121.8(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.379(10)
C1 C2 . 1.392(8)
C1 N1 . 1.435(7)
C2 C3 . 1.395(7)
C2 C15 . 1.500(8)
C3 C4 . 1.359(9)
C3 C16 . 1.516(8)
C4 C5 . 1.375(9)
C4 H4 . 0.9300
C5 C6 . 1.395(9)
C5 H5 . 0.9300
C6 C7 . 1.495(9)
C7 C8 . 1.273(9)
C7 C9 . 1.523(9)
C8 H8A . 0.9300
C8 H8B . 0.9300
C9 C10 . 1.364(9)
C9 C14 . 1.373(9)
C10 C11 . 1.381(9)
C10 H10 . 0.9300
C11 C12 . 1.350(9)
C11 H11 . 0.9300
C12 C13 . 1.356(9)
C12 H12 . 0.9300
C13 C14 . 1.381(9)
C13 H13 . 0.9300
C14 H14 . 0.9300
C15 H15A . 0.9600
C15 H15B . 0.9600
C15 H15C . 0.9600
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
C17 N1 . 1.261(6)
C17 C17 3_676 1.502(10)
C17 C18 . 1.506(7)
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_site_symmetry_1
_geom_torsion
C6 C1 C2 C3 . 3.4(7)
N1 C1 C2 C3 . 175.4(4)
C6 C1 C2 C15 . -174.9(5)
N1 C1 C2 C15 . -2.9(7)
C1 C2 C3 C4 . 0.1(7)
C15 C2 C3 C4 . 178.4(5)
C1 C2 C3 C16 . 179.4(5)
C15 C2 C3 C16 . -2.4(7)
C2 C3 C4 C5 . -2.9(8)
C16 C3 C4 C5 . 177.9(5)
C3 C4 C5 C6 . 2.2(9)
C2 C1 C6 C5 . -4.1(8)
N1 C1 C6 C5 . -176.1(5)
C2 C1 C6 C7 . 174.6(5)
N1 C1 C6 C7 . 2.5(8)
C4 C5 C6 C1 . 1.3(9)
C4 C5 C6 C7 . -177.4(6)
C1 C6 C7 C8 . -108.0(11)
C5 C6 C7 C8 . 70.6(13)
C1 C6 C7 C9 . 74.5(10)
C5 C6 C7 C9 . -106.9(8)
C8 C7 C9 C10 . 44.8(14)
C6 C7 C9 C10 . -137.7(8)
C8 C7 C9 C14 . -132.8(10)
C6 C7 C9 C14 . 44.7(12)
C14 C9 C10 C11 . -0.8(11)
C7 C9 C10 C11 . -178.5(7)
C9 C10 C11 C12 . 1.1(11)
C10 C11 C12 C13 . -0.8(11)
C11 C12 C13 C14 . 0.1(11)
C10 C9 C14 C13 . 0.1(11)
C7 C9 C14 C13 . 177.9(7)
C12 C13 C14 C9 . 0.2(11)
C17 C17 N1 C1 3_676 -179.8(7)
C18 C17 N1 C1 . 1.9(12)
C6 C1 N1 C17 . -106.0(7)
C2 C1 N1 C17 . 81.6(8)
