#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/27/2212748.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_2212748
loop_
_publ_author_name
'Xiu-Ying Yang'
'Yu-Feng Li'
'Jian Zheng'
'Fang-Fang Jian'
_publ_section_title
;
 N-3,5-Dimethyl-[1-(4-nitrophenyl)ethylidene]aniline
;
_journal_coeditor_code           AT2207
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1611
_journal_page_last               o1612
_journal_paper_doi               10.1107/S1600536807001365
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C16 H16 N2 O2'
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_chemical_name_systematic
;
N-3,5-Dimethyl-[1-(4-nitrophenyl)ethylidene]aniline
;
_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                 96.35(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.5850(17)
_cell_length_b                   7.1820(14)
_cell_length_c                   23.786(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.95
_cell_measurement_theta_min      1.72
_cell_volume                     1457.6(5)
_computing_cell_refinement       'CAD-4-PC Software'
_computing_data_collection       'CAD-4-PC Software (Enraf--Nonius, 1992)'
_computing_data_reduction        'NRCVAX (Gabe et al.,  1989)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3335
_diffrn_reflns_theta_full        26.95
_diffrn_reflns_theta_max         26.95
_diffrn_reflns_theta_min         1.72
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1594
_refine_ls_R_factor_gt           0.0645
_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)+(0.1245P)²+0.0362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.2357
_reflns_number_gt                1342
_reflns_number_total             3130
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2207.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212748
_cod_database_fobs_code          2212748
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_occupancy
C C1 0.1433(4) 1.0886(5) -0.05903(13) 0.0670(8) Uani d 1
C C2 0.2483(4) 1.1680(5) -0.01796(15) 0.0768(9) Uani d 1
H H2 0.2729 1.2938 -0.0196 0.080 Uiso calc 1
C C3 0.3165(3) 1.0583(5) 0.02560(13) 0.0695(9) Uani d 1
H H3 0.3875 1.1108 0.0535 0.080 Uiso calc 1
C C4 0.2800(3) 0.8691(4) 0.02827(12) 0.0617(8) Uani d 1
C C5 0.1750(4) 0.7935(4) -0.01451(12) 0.0653(8) Uani d 1
H H5 0.1509 0.6673 -0.0136 0.080 Uiso calc 1
C C6 0.1061(4) 0.9022(5) -0.05809(12) 0.0698(9) Uani d 1
H H6 0.0358 0.8505 -0.0864 0.080 Uiso calc 1
C C7 0.3722(4) 0.4621(4) 0.12301(12) 0.0638(8) Uani d 1
C C8 0.5295(4) 0.4046(4) 0.13398(13) 0.0682(8) Uani d 1
H H8 0.6024 0.4422 0.1101 0.080 Uiso calc 1
C C9 0.5760(3) 0.2922(4) 0.18014(13) 0.0651(8) Uani d 1
C C10 0.4628(3) 0.2340(4) 0.21488(12) 0.0651(8) Uani d 1
H H10 0.4926 0.1578 0.2458 0.080 Uiso calc 1
C C11 0.3051(3) 0.2893(4) 0.20349(13) 0.0647(8) Uani d 1
C C12 0.2619(3) 0.4008(4) 0.15772(13) 0.0673(8) Uani d 1
H H12 0.1576 0.4360 0.1497 0.080 Uiso calc 1
C C13 0.3459(3) 0.7516(4) 0.07781(12) 0.0615(8) Uani d 1
C C14 0.4314(5) 0.8501(5) 0.12721(14) 0.0900(11) Uani d 1
H H14A 0.4691 0.7607 0.1555 0.080 Uiso calc 1
H H14B 0.3617 0.9356 0.1428 0.080 Uiso calc 1
H H14C 0.5185 0.9172 0.1151 0.080 Uiso calc 1
C C15 0.1860(4) 0.2223(5) 0.24078(14) 0.0885(11) Uani d 1
H H15A 0.2371 0.1475 0.2708 0.080 Uiso calc 1
H H15B 0.1079 0.1492 0.2188 0.080 Uiso calc 1
H H15C 0.1371 0.3274 0.2565 0.080 Uiso calc 1
C C16 0.7449(4) 0.2316(5) 0.19295(15) 0.0878(11) Uani d 1
H H16A 0.7556 0.1548 0.2262 0.080 Uiso calc 1
H H16B 0.8106 0.3394 0.1993 0.080 Uiso calc 1
H H16C 0.7758 0.1622 0.1615 0.080 Uiso calc 1
N N1 0.0686(3) 1.2085(5) -0.10508(13) 0.0804(8) Uani d 1
N N2 0.3202(3) 0.5776(3) 0.07516(10) 0.0688(7) Uani d 1
O O1 0.1035(3) 1.3728(5) -0.10528(13) 0.1193(11) Uani d 1
O O2 -0.0281(3) 1.1373(4) -0.14001(11) 0.1054(9) Uani d 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'
O O 0.0106 0.0060 '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
C6 C1 C2 121.7(3)
C6 C1 N1 119.7(3)
C2 C1 N1 118.6(3)
C1 C2 C3 119.1(3)
C1 C2 H2 120.5
C3 C2 H2 120.5
C2 C3 C4 120.7(3)
C2 C3 H3 119.6
C4 C3 H3 119.6
C5 C4 C3 118.4(3)
C5 C4 C13 120.6(3)
C3 C4 C13 120.9(3)
C6 C5 C4 121.2(3)
C6 C5 H5 119.4
C4 C5 H5 119.4
C1 C6 C5 118.8(3)
C1 C6 H6 120.6
C5 C6 H6 120.6
C12 C7 C8 119.8(3)
C12 C7 N2 118.6(3)
C8 C7 N2 121.5(3)
C9 C8 C7 120.3(3)
C9 C8 H8 119.9
C7 C8 H8 119.9
C8 C9 C10 118.8(3)
C8 C9 C16 120.9(3)
C10 C9 C16 120.3(3)
C9 C10 C11 121.0(3)
C9 C10 H10 119.5
C11 C10 H10 119.5
C12 C11 C10 119.2(3)
C12 C11 C15 120.9(3)
C10 C11 C15 119.9(3)
C11 C12 C7 120.9(3)
C11 C12 H12 119.6
C7 C12 H12 119.6
N2 C13 C14 125.0(3)
N2 C13 C4 117.7(3)
C14 C13 C4 117.3(3)
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
C11 C15 H15A 109.5
C11 C15 H15B 109.5
H15A C15 H15B 109.5
C11 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C9 C16 H16A 109.5
C9 C16 H16B 109.5
H16A C16 H16B 109.5
C9 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
O1 N1 O2 123.6(3)
O1 N1 C1 118.7(3)
O2 N1 C1 117.7(3)
C13 N2 C7 119.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.377(4)
C1 C2 1.378(4)
C1 N1 1.482(4)
C2 C3 1.379(4)
C2 H2 0.9300
C3 C4 1.397(4)
C3 H3 0.9300
C4 C5 1.393(4)
C4 C13 1.508(4)
C5 C6 1.377(4)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.395(4)
C7 C8 1.409(4)
C7 N2 1.439(4)
C8 C9 1.386(4)
C8 H8 0.9300
C9 C10 1.407(4)
C9 C16 1.512(4)
C10 C11 1.408(4)
C10 H10 0.9300
C11 C12 1.369(4)
C11 C15 1.505(4)
C12 H12 0.9300
C13 N2 1.269(4)
C13 C14 1.493(4)
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
N1 O1 1.217(4)
N1 O2 1.220(4)
