#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205873.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_2205873
loop_
_publ_author_name
'Quail, J. Wilson'
'Doroudi, Alireza'
'Pati, Hari N.'
'Das, Umashankar'
'Dimmock, Jonathan R.'
_publ_section_title
(E,E)-2-(4-Methylphenylmethylene)-6-(4-nitrophenylmethylene)cyclohexanone
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1795
_journal_page_last               o1797
_journal_paper_doi               10.1107/S1600536805015102
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C21 H19 N O3'
_chemical_formula_moiety         'C21 H19 N O3'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_name_systematic
;
(E,E)-2-(4-Methylphenylmethylene)-6-(4-nitrophenylmethylene)cyclohexanone
;
_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                 101.550(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.5713(3)
_cell_length_b                   10.9972(4)
_cell_length_c                   20.0451(6)
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.034
_cell_measurement_theta_min      0.998
_cell_volume                     1635.22(10)
_computing_cell_refinement       'SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2000)'
_computing_data_reduction
'SCALEPACK and DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offsets'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0484
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6518
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chip
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.236
_refine_ls_extinction_coef       0.0110(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0478
_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)+(0.0621P)²+0.3697P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1297
_reflns_number_gt                2252
_reflns_number_total             3354
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6665.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205873
_cod_database_fobs_code          2205873
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_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_type_symbol
N1 1.0235(2) 0.92058(17) 0.85261(8) 0.0387(4) Uani d . 1 N
O1 0.7513(2) 1.02782(14) 0.43299(7) 0.0503(4) Uani d . 1 O
O2 1.1505(2) 0.98567(15) 0.87954(7) 0.0514(4) Uani d . 1 O
O3 0.9576(2) 0.84253(17) 0.88339(8) 0.0577(5) Uani d . 1 O
C1 0.6773(3) 0.93328(17) 0.44521(9) 0.0308(4) Uani d . 1 C
C2 0.5697(2) 0.85971(17) 0.38862(9) 0.0274(4) Uani d . 1 C
C3 0.4876(3) 0.74196(17) 0.40561(9) 0.0328(5) Uani d . 1 C
H3A 0.4835 0.6841 0.3675 0.039 Uiso calc R 1 H
H3B 0.3622 0.7570 0.4109 0.039 Uiso calc R 1 H
C4 0.5940(3) 0.68561(18) 0.47078(9) 0.0362(5) Uani d . 1 C
H4A 0.5331 0.6102 0.4810 0.043 Uiso calc R 1 H
H4B 0.7159 0.6635 0.4640 0.043 Uiso calc R 1 H
C5 0.6108(3) 0.77195(17) 0.53077(9) 0.0327(5) Uani d . 1 C
H5A 0.4897 0.7860 0.5409 0.039 Uiso calc R 1 H
H5B 0.6866 0.7336 0.5713 0.039 Uiso calc R 1 H
C6 0.6921(2) 0.89241(17) 0.51783(9) 0.0282(4) Uani d . 1 C
C7 0.7803(2) 0.96795(17) 0.56568(9) 0.0289(4) Uani d . 1 C
H7 0.8190 1.0418 0.5486 0.035 Uiso calc R 1 H
C8 0.8266(2) 0.95536(17) 0.63999(9) 0.0276(4) Uani d . 1 C
C9 0.9636(2) 1.03177(18) 0.67446(10) 0.0314(4) Uani d . 1 C
H9 1.0144 1.0910 0.6494 0.038 Uiso calc R 1 H
C10 1.0262(2) 1.02299(18) 0.74380(9) 0.0321(5) Uani d . 1 C
H10 1.1188 1.0754 0.7665 0.039 Uiso calc R 1 H
C11 0.9512(2) 0.93627(18) 0.77961(9) 0.0295(4) Uani d . 1 C
C12 0.8099(3) 0.86285(18) 0.74860(9) 0.0322(5) Uani d . 1 C
H12 0.7573 0.8059 0.7745 0.039 Uiso calc R 1 H
C13 0.7467(2) 0.87400(18) 0.67903(9) 0.0312(5) Uani d . 1 C
H13 0.6475 0.8258 0.6574 0.037 Uiso calc R 1 H
C14 0.5531(2) 0.90804(17) 0.32576(9) 0.0270(4) Uani d . 1 C
H14 0.6214 0.9802 0.3247 0.032 Uiso calc R 1 H
C15 0.4507(2) 0.87149(16) 0.25886(9) 0.0254(4) Uani d . 1 C
C16 0.4833(3) 0.93674(17) 0.20244(9) 0.0310(5) Uani d . 1 C
H16 0.5752 0.9969 0.2091 0.037 Uiso calc R 1 H
C17 0.3858(3) 0.91613(18) 0.13736(9) 0.0322(5) Uani d . 1 C
H17 0.4130 0.9617 0.1005 0.039 Uiso calc R 1 H
C18 0.2491(2) 0.83030(17) 0.12487(9) 0.0292(4) Uani d . 1 C
C19 0.2194(3) 0.76272(18) 0.18041(10) 0.0331(5) Uani d . 1 C
H19 0.1298 0.7010 0.1732 0.040 Uiso calc R 1 H
C20 0.3160(2) 0.78244(18) 0.24571(9) 0.0314(4) Uani d . 1 C
H20 0.2906 0.7348 0.2822 0.038 Uiso calc R 1 H
C21 0.1338(3) 0.8143(2) 0.05507(10) 0.0380(5) Uani d . 1 C
H21A 0.1065 0.7279 0.0469 0.046 Uiso calc R 1 H
H21B 0.1986 0.8449 0.0208 0.046 Uiso calc R 1 H
H21C 0.0212 0.8599 0.0521 0.046 Uiso calc R 1 H
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
O3 N1 O2 123.29(17)
O3 N1 C11 118.60(17)
O2 N1 C11 118.09(18)
O1 C1 C2 120.51(17)
O1 C1 C6 119.77(17)
C2 C1 C6 119.71(16)
C14 C2 C1 115.47(17)
C14 C2 C3 125.76(16)
C1 C2 C3 118.76(16)
C2 C3 C4 111.88(15)
C2 C3 H3A 109.2
C4 C3 H3A 109.2
C2 C3 H3B 109.2
C4 C3 H3B 109.2
H3A C3 H3B 107.9
C5 C4 C3 111.79(16)
C5 C4 H4A 109.3
C3 C4 H4A 109.3
C5 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 107.9
C6 C5 C4 112.73(15)
C6 C5 H5A 109.0
C4 C5 H5A 109.0
C6 C5 H5B 109.0
C4 C5 H5B 109.0
H5A C5 H5B 107.8
C7 C6 C5 125.73(17)
C7 C6 C1 115.88(17)
C5 C6 C1 118.39(16)
C6 C7 C8 130.65(18)
C6 C7 H7 114.7
C8 C7 H7 114.7
C13 C8 C9 117.76(16)
C13 C8 C7 125.74(16)
C9 C8 C7 116.50(17)
C10 C9 C8 121.66(18)
C10 C9 H9 119.2
C8 C9 H9 119.2
C9 C10 C11 118.54(17)
C9 C10 H10 120.7
C11 C10 H10 120.7
C10 C11 C12 122.01(17)
C10 C11 N1 119.32(17)
C12 C11 N1 118.67(18)
C11 C12 C13 118.70(18)
C11 C12 H12 120.6
C13 C12 H12 120.6
C12 C13 C8 121.11(17)
C12 C13 H13 119.4
C8 C13 H13 119.4
C2 C14 C15 132.85(18)
C2 C14 H14 113.6
C15 C14 H14 113.6
C20 C15 C16 116.43(16)
C20 C15 C14 126.62(16)
C16 C15 C14 116.85(16)
C17 C16 C15 121.99(18)
C17 C16 H16 119.0
C15 C16 H16 119.0
C16 C17 C18 121.36(18)
C16 C17 H17 119.3
C18 C17 H17 119.3
C17 C18 C19 116.93(17)
C17 C18 C21 121.39(17)
C19 C18 C21 121.64(17)
C20 C19 C18 122.23(18)
C20 C19 H19 118.9
C18 C19 H19 118.9
C19 C20 C15 121.01(17)
C19 C20 H20 119.5
C15 C20 H20 119.5
C18 C21 H21A 109.5
C18 C21 H21B 109.5
H21A C21 H21B 109.5
C18 C21 H21C 109.5
H21A C21 H21C 109.5
H21B C21 H21C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 O3 1.220(2)
N1 O2 1.233(2)
N1 C11 1.466(2)
O1 C1 1.229(2)
C1 C2 1.495(3)
C1 C6 1.506(3)
C2 C14 1.350(3)
C2 C3 1.505(3)
C3 C4 1.523(3)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.517(3)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.505(3)
C5 H5A 0.9900
C5 H5B 0.9900
C6 C7 1.341(3)
C7 C8 1.467(2)
C7 H7 0.9500
C8 C13 1.403(3)
C8 C9 1.404(3)
C9 C10 1.379(3)
C9 H9 0.9500
C10 C11 1.382(3)
C10 H10 0.9500
C11 C12 1.385(3)
C12 C13 1.386(3)
C12 H12 0.9500
C13 H13 0.9500
C14 C15 1.464(2)
C14 H14 0.9500
C15 C20 1.400(3)
C15 C16 1.402(3)
C16 C17 1.383(3)
C16 H16 0.9500
C17 C18 1.386(3)
C17 H17 0.9500
C18 C19 1.394(3)
C18 C21 1.504(3)
C19 C20 1.383(3)
C19 H19 0.9500
C20 H20 0.9500
C21 H21A 0.9800
C21 H21B 0.9800
C21 H21C 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
O1 C1 C2 C14 -3.5(3)
C6 C1 C2 C14 175.30(16)
O1 C1 C2 C3 177.55(19)
C6 C1 C2 C3 -3.6(3)
C14 C2 C3 C4 154.16(18)
C1 C2 C3 C4 -27.1(2)
C2 C3 C4 C5 56.9(2)
C3 C4 C5 C6 -55.5(2)
C4 C5 C6 C7 -155.15(19)
C4 C5 C6 C1 24.0(2)
O1 C1 C6 C7 3.4(3)
C2 C1 C6 C7 -175.43(16)
O1 C1 C6 C5 -175.85(18)
C2 C1 C6 C5 5.3(3)
C5 C6 C7 C8 2.3(3)
C1 C6 C7 C8 -176.94(17)
C6 C7 C8 C13 -18.2(3)
C6 C7 C8 C9 161.64(19)
C13 C8 C9 C10 3.9(3)
C7 C8 C9 C10 -175.98(17)
C8 C9 C10 C11 0.1(3)
C9 C10 C11 C12 -3.4(3)
C9 C10 C11 N1 176.32(17)
O3 N1 C11 C10 -179.01(18)
O2 N1 C11 C10 -0.4(3)
O3 N1 C11 C12 0.7(3)
O2 N1 C11 C12 179.32(17)
C10 C11 C12 C13 2.4(3)
N1 C11 C12 C13 -177.26(16)
C11 C12 C13 C8 1.8(3)
C9 C8 C13 C12 -4.8(3)
C7 C8 C13 C12 175.02(18)
C1 C2 C14 C15 -174.69(18)
C3 C2 C14 C15 4.1(3)
C2 C14 C15 C20 11.5(3)
C2 C14 C15 C16 -172.4(2)
C20 C15 C16 C17 1.2(3)
C14 C15 C16 C17 -175.38(17)
C15 C16 C17 C18 0.7(3)
C16 C17 C18 C19 -2.4(3)
C16 C17 C18 C21 175.36(18)
C17 C18 C19 C20 2.4(3)
C21 C18 C19 C20 -175.34(18)
C18 C19 C20 C15 -0.6(3)
C16 C15 C20 C19 -1.2(3)
C14 C15 C20 C19 174.99(18)
