#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/82/2018218.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_2018218
loop_
_publ_author_name
'Collas, Alain'
'Blockhuys, Frank'
_publ_section_title
;
 (E)-4-[2-(3,4,5-Trimethoxyphenyl)ethenyl]nitrobenzene and its
 `bridge-flipped' analogues
;
_journal_coeditor_code           FA3256
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o364
_journal_page_last               o369
_journal_paper_doi               10.1107/S0108270111030952
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C17 H17 N O5'
_chemical_formula_moiety         'C17 H17 N O5'
_chemical_formula_sum            'C17 H17 N O5'
_chemical_formula_weight         315.32
_chemical_name_common            (E)-3,4,5-trimethoxy-4'-nitrostilbene
_chemical_name_systematic
;
(E)-1-nitro-4-[2-(3,4,5-trimethoxyphenyl)ethenyl]benzene
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 124.069(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.459(2)
_cell_length_b                   12.880(10)
_cell_length_c                   14.021(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      10.13
_cell_measurement_theta_min      5.42
_cell_volume                     1564.6(14)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1996)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       θ/2ω
_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  0.0426
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5901
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         2.35
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.346
_refine_diff_density_min         -0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2867
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0454
_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)+(0.0536P)²+0.4441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1346
_reflns_number_gt                1500
_reflns_number_total             2867
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fa3256.cif
_cod_data_source_block           I
_cod_original_cell_volume        1564.6(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2018218
_cod_database_fobs_code          2018218
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 0.2949(3) 0.6123(2) 0.0449(2) 0.0500(6) Uani d . 1 1
C C2 0.2913(3) 0.55632(19) -0.0414(2) 0.0512(6) Uani d . 1 1
H H2 0.2611 0.4870 -0.0537 0.061 Uiso calc R 1 1
C C3 0.3328(3) 0.6036(2) -0.1089(2) 0.0500(6) Uani d . 1 1
C C4 0.3792(3) 0.70753(19) -0.0895(2) 0.0484(6) Uani d . 1 1
C C5 0.3820(3) 0.7628(2) -0.0030(2) 0.0519(6) Uani d . 1 1
C C6 0.3401(3) 0.7153(2) 0.0635(2) 0.0532(7) Uani d . 1 1
H H6 0.3422 0.7526 0.1212 0.064 Uiso calc R 1 1
C C7 0.2517(3) 0.5678(2) 0.1199(2) 0.0592(7) Uani d . 1 1
H H7 0.2756 0.6078 0.1832 0.071 Uiso calc R 1 1
C C8 0.1847(3) 0.4801(2) 0.1088(2) 0.0583(7) Uani d . 1 1
H H8 0.1619 0.4384 0.0470 0.070 Uiso calc R 1 1
C C9 0.1411(3) 0.4402(2) 0.1861(2) 0.0512(6) Uani d . 1 1
C C14 0.0873(3) 0.3402(2) 0.1730(2) 0.0595(7) Uani d . 1 1
H H14 0.0774 0.2988 0.1148 0.071 Uiso calc R 1 1
C C13 0.0482(3) 0.3004(2) 0.2437(2) 0.0585(7) Uani d . 1 1
H H13 0.0135 0.2323 0.2346 0.070 Uiso calc R 1 1
C C12 0.0607(3) 0.3618(2) 0.3282(2) 0.0520(6) Uani d . 1 1
C C11 0.1111(3) 0.4624(2) 0.3438(2) 0.0609(7) Uani d . 1 1
H H11 0.1174 0.5036 0.4008 0.073 Uiso calc R 1 1
C C10 0.1525(3) 0.5014(2) 0.2726(2) 0.0597(7) Uani d . 1 1
H H10 0.1884 0.5693 0.2826 0.072 Uiso calc R 1 1
C C31 0.2920(4) 0.4510(2) -0.2184(3) 0.0751(9) Uani d . 1 1
H H31A 0.1897 0.4416 -0.2362 0.113 Uiso calc R 1 1
H H31B 0.3638 0.4110 -0.1514 0.113 Uiso calc R 1 1
H H31C 0.2949 0.4283 -0.2823 0.113 Uiso calc R 1 1
C C51 0.4430(4) 0.9222(2) 0.1004(3) 0.0788(9) Uani d . 1 1
H H51A 0.5192 0.8903 0.1724 0.118 Uiso calc R 1 1
H H51B 0.3457 0.9238 0.0924 0.118 Uiso calc R 1 1
H H51C 0.4744 0.9918 0.0985 0.118 Uiso calc R 1 1
C C411 0.5782(4) 0.7551(3) -0.1094(3) 0.0818(9) Uani d . 1 1
H H41A 0.6136 0.6847 -0.1002 0.123 Uiso calc R 1 1
H H41B 0.6322 0.7889 -0.0357 0.123 Uiso calc R 1 1
H H41C 0.5977 0.7914 -0.1598 0.123 Uiso calc R 1 1
N N1 0.0198(3) 0.3190(2) 0.4046(2) 0.0728(7) Uani d . 1 1
O O1 0.0234(3) 0.3758(2) 0.4752(2) 0.1155(9) Uani d . 1 1
O O2 -0.0113(3) 0.2273(2) 0.3958(2) 0.1119(9) Uani d . 1 1
O O3 0.3325(2) 0.55781(14) -0.19659(15) 0.0661(5) Uani d . 1 1
O O4 0.4183(2) 0.75565(14) -0.15702(14) 0.0608(5) Uani d . 1 1
O O5 0.4280(2) 0.86429(14) 0.00886(15) 0.0674(5) 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'
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 120.0(2)
C6 C1 C7 116.6(2)
C2 C1 C7 123.3(2)
C3 C2 C1 120.1(2)
C3 C2 H2 120.0
C1 C2 H2 120.0
O3 C3 C2 125.7(2)
O3 C3 C4 114.6(2)
C2 C3 C4 119.7(2)
O4 C4 C5 120.1(2)
O4 C4 C3 120.2(2)
C5 C4 C3 119.7(2)
O5 C5 C6 124.4(2)
O5 C5 C4 115.4(2)
C6 C5 C4 120.2(3)
C5 C6 C1 120.2(2)
C5 C6 H6 119.9
C1 C6 H6 119.9
C8 C7 C1 128.1(3)
C8 C7 H7 116.0
C1 C7 H7 116.0
C7 C8 C9 125.6(3)
C7 C8 H8 117.2
C9 C8 H8 117.2
C14 C9 C10 118.4(2)
C14 C9 C8 119.8(2)
C10 C9 C8 121.8(2)
C13 C14 C9 121.3(3)
C13 C14 H14 119.3
C9 C14 H14 119.3
C14 C13 C12 119.3(3)
C14 C13 H13 120.3
C12 C13 H13 120.3
C13 C12 C11 121.8(2)
C13 C12 N1 119.3(3)
C11 C12 N1 118.9(3)
C12 C11 C10 118.4(3)
C12 C11 H11 120.8
C10 C11 H11 120.8
C11 C10 C9 120.8(3)
C11 C10 H10 119.6
C9 C10 H10 119.6
O3 C31 H31A 109.5
O3 C31 H31B 109.5
H31A C31 H31B 109.5
O3 C31 H31C 109.5
H31A C31 H31C 109.5
H31B C31 H31C 109.5
O5 C51 H51A 109.5
O5 C51 H51B 109.5
H51A C51 H51B 109.5
O5 C51 H51C 109.5
H51A C51 H51C 109.5
H51B C51 H51C 109.5
O4 C411 H41A 109.5
O4 C411 H41B 109.5
H41A C411 H41B 109.5
O4 C411 H41C 109.5
H41A C411 H41C 109.5
H41B C411 H41C 109.5
O2 N1 O1 123.6(3)
O2 N1 C12 117.6(3)
O1 N1 C12 118.8(3)
C3 O3 C31 117.5(2)
C4 O4 C411 113.8(2)
C5 O5 C51 117.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.383(4)
C1 C2 1.392(3)
C1 C7 1.474(3)
C2 C3 1.384(3)
C2 H2 0.9300
C3 O3 1.362(3)
C3 C4 1.398(4)
C4 O4 1.372(3)
C4 C5 1.392(3)
C5 O5 1.370(3)
C5 C6 1.377(3)
C6 H6 0.9300
C7 C8 1.291(4)
C7 H7 0.9300
C8 C9 1.484(3)
C8 H8 0.9300
C9 C14 1.377(4)
C9 C10 1.394(3)
C14 C13 1.366(4)
C14 H14 0.9300
C13 C12 1.369(4)
C13 H13 0.9300
C12 C11 1.369(4)
C12 N1 1.464(3)
C11 C10 1.387(3)
C11 H11 0.9300
C10 H10 0.9300
C31 O3 1.421(3)
C31 H31A 0.9600
C31 H31B 0.9600
C31 H31C 0.9600
C51 O5 1.415(3)
C51 H51A 0.9600
C51 H51B 0.9600
C51 H51C 0.9600
C411 O4 1.411(3)
C411 H41A 0.9600
C411 H41B 0.9600
C411 H41C 0.9600
N1 O2 1.214(3)
N1 O1 1.215(3)
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
C6 C1 C2 C3 -0.1(4)
C7 C1 C2 C3 179.7(2)
C1 C2 C3 O3 -179.2(2)
C1 C2 C3 C4 0.4(3)
O3 C3 C4 O4 0.7(3)
C2 C3 C4 O4 -179.0(2)
O3 C3 C4 C5 179.1(2)
C2 C3 C4 C5 -0.6(3)
O4 C4 C5 O5 -1.1(3)
C3 C4 C5 O5 -179.5(2)
O4 C4 C5 C6 178.8(2)
C3 C4 C5 C6 0.4(4)
O5 C5 C6 C1 179.9(2)
C4 C5 C6 C1 0.0(4)
C2 C1 C6 C5 -0.1(4)
C7 C1 C6 C5 -179.9(2)
C6 C1 C7 C8 168.7(3)
C2 C1 C7 C8 -11.1(4)
C1 C7 C8 C9 -178.7(2)
C7 C8 C9 C14 -172.1(3)
C7 C8 C9 C10 8.0(4)
C10 C9 C14 C13 -1.1(4)
C8 C9 C14 C13 179.0(2)
C9 C14 C13 C12 1.0(4)
C14 C13 C12 C11 0.1(4)
C14 C13 C12 N1 -179.6(2)
C13 C12 C11 C10 -1.0(4)
N1 C12 C11 C10 178.7(2)
C12 C11 C10 C9 0.9(4)
C14 C9 C10 C11 0.2(4)
C8 C9 C10 C11 -180.0(2)
C13 C12 N1 O2 6.1(4)
C11 C12 N1 O2 -173.6(3)
C13 C12 N1 O1 -176.1(3)
C11 C12 N1 O1 4.2(4)
C2 C3 O3 C31 -2.6(4)
C4 C3 O3 C31 177.8(2)
C5 C4 O4 C411 86.2(3)
C3 C4 O4 C411 -95.4(3)
C6 C5 O5 C51 4.3(4)
C4 C5 O5 C51 -175.8(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11294868
