#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/54/2005457.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_2005457
loop_
_publ_author_name
'Clegg, W.'
'Elsegood, M. R. J.'
'Heath, S. L.'
'Houlton, A.'
'Shipman, M. A.'
_publ_section_title
;
 Conformational Flexibility in N-Benzylideneanilines
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2548
_journal_page_last               2552
_journal_paper_doi               10.1107/S0108270196009225
_journal_volume                  52
_journal_year                    1996
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_chemical_name_systematic
;
 p-nitro-N-(p-methoxybenzylidene)aniline
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.000(2)
_cell_angle_beta                 99.642(2)
_cell_angle_gamma                90.000(2)
_cell_formula_units_Z            8
_cell_length_a                   11.4508(10)
_cell_length_b                   7.3793(7)
_cell_length_c                   29.047(3)
_cell_measurement_reflns_used    6209
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      2.85
_cell_volume                     2419.8(4)
_computing_cell_refinement       'local programs'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12225
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.42
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.200
_refine_ls_extinction_coef       0.0027(4)
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1995)'
_refine_ls_goodness_of_fit_all   1.063
_refine_ls_goodness_of_fit_obs   1.077
_refine_ls_hydrogen_treatment    'H atoms riding (see below)'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4260
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_restrained_S_obs      1.077
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_obs          0.0386
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.7611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1061
_refine_ls_wR_factor_obs         0.0937
_reflns_number_observed          3314
_reflns_number_total             4260
_reflns_observed_criterion       >2\s(I)
_cod_data_source_file            ab1402.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.7611P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0487P)^2^+0.7611P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2005457
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1 1 0.74678(11) 0.59374(19) -0.14399(4) 0.0418(3) Uani d . O
O2 1 0.56733(11) 0.65672(18) -0.17618(4) 0.0399(3) Uani d . O
N1 1 0.64361(12) 0.63512(19) -0.14161(5) 0.0308(3) Uani d . N
C1 1 0.61159(14) 0.6607(2) -0.09542(5) 0.0261(4) Uani d . C
C2 1 0.49467(14) 0.6950(2) -0.09207(6) 0.0288(4) Uani d . C
H2 1 0.4361 0.7005 -0.1194 0.035 Uiso calc R H
C3 1 0.46390(14) 0.7211(2) -0.04872(6) 0.0292(4) Uani d . C
H3 1 0.3833 0.7413 -0.0462 0.035 Uiso calc R H
C4 1 0.54996(13) 0.7181(2) -0.00839(6) 0.0255(4) Uani d . C
C5 1 0.66725(14) 0.6825(2) -0.01292(6) 0.0305(4) Uani d . C
H5 1 0.7264 0.6781 0.0142 0.037 Uiso calc R H
C6 1 0.69862(14) 0.6534(2) -0.05622(6) 0.0316(4) Uani d . C
H6 1 0.7786 0.6287 -0.0590 0.038 Uiso calc R H
N2 1 0.52740(11) 0.74359(19) 0.03741(5) 0.0277(3) Uani d . N
C7 1 0.42926(14) 0.8109(2) 0.04449(6) 0.0277(4) Uani d . C
H7 1 0.3724 0.8474 0.0185 0.033 Uiso calc R H
C8 1 0.40201(13) 0.8332(2) 0.09130(5) 0.0249(4) Uani d . C
C9 1 0.29548(14) 0.9109(2) 0.09839(6) 0.0276(4) Uani d . C
H9 1 0.2385 0.9451 0.0722 0.033 Uiso calc R H
C10 1 0.27126(14) 0.9390(2) 0.14307(6) 0.0278(4) Uani d . C
H10 1 0.1984 0.9926 0.1474 0.033 Uiso calc R H
C11 1 0.35394(14) 0.8886(2) 0.18143(6) 0.0255(4) Uani d . C
C12 1 0.45998(14) 0.8062(2) 0.17486(6) 0.0297(4) Uani d . C
H12 1 0.5160 0.7687 0.2010 0.036 Uiso calc R H
C13 1 0.48267(13) 0.7799(2) 0.13055(6) 0.0276(4) Uani d . C
H13 1 0.5549 0.7241 0.1264 0.033 Uiso calc R H
O3 1 0.34108(10) 0.91301(16) 0.22686(4) 0.0330(3) Uani d . O
C14 1 0.24133(16) 1.0169(3) 0.23568(6) 0.0382(4) Uani d . C
H14A 1 0.2466 1.0349 0.2694 0.057 Uiso calc R H
H14B 1 0.1680 0.9520 0.2235 0.057 Uiso calc R H
H14C 1 0.2412 1.1350 0.2202 0.057 Uiso calc R H
O4 1 0.84749(12) 0.1158(2) 0.02056(4) 0.0562(4) Uani d . O
O5 1 1.02618(11) 0.1903(2) 0.05005(4) 0.0470(4) Uani d . O
N3 1 0.92548(13) 0.1453(2) 0.05406(5) 0.0353(4) Uani d . N
C15 1 0.89666(14) 0.1275(2) 0.10102(6) 0.0273(4) Uani d . C
C16 1 0.79105(14) 0.0450(2) 0.10647(6) 0.0283(4) Uani d . C
H16 1 0.7398 -0.0043 0.0804 0.034 Uiso calc R H
C17 1 0.76200(14) 0.0360(2) 0.15061(6) 0.0266(4) Uani d . C
H17 1 0.6900 -0.0201 0.1549 0.032 Uiso calc R H
C18 1 0.83706(14) 0.1084(2) 0.18894(6) 0.0248(4) Uani d . C
C19 1 0.94510(13) 0.1845(2) 0.18268(6) 0.0260(4) Uani d . C
H19 1 0.9984 0.2287 0.2089 0.031 Uiso calc R H
C20 1 0.97475(13) 0.1956(2) 0.13858(6) 0.0267(4) Uani d . C
H20 1 1.0475 0.2490 0.1341 0.032 Uiso calc R H
N4 1 0.81133(11) 0.10037(18) 0.23477(5) 0.0272(3) Uani d . N
C21 1 0.70560(14) 0.1318(2) 0.24128(6) 0.0265(4) Uani d . C
H21 1 0.6474 0.1646 0.2153 0.032 Uiso calc R H
C22 1 0.67146(13) 0.1189(2) 0.28723(6) 0.0248(4) Uani d . C
C23 1 0.55873(14) 0.1722(2) 0.29386(6) 0.0278(4) Uani d . C
H23 1 0.5032 0.2122 0.2678 0.033 Uiso calc R H
C24 1 0.52589(14) 0.1679(2) 0.33768(6) 0.0282(4) Uani d . C
H24 1 0.4484 0.2032 0.3416 0.034 Uiso calc R H
C25 1 0.60768(14) 0.1113(2) 0.37574(6) 0.0257(4) Uani d . C
C26 1 0.72032(14) 0.0557(2) 0.36969(6) 0.0259(4) Uani d . C
H26 1 0.7757 0.0158 0.3958 0.031 Uiso calc R H
C27 1 0.75158(14) 0.0583(2) 0.32607(6) 0.0250(4) Uani d . C
H27 1 0.8282 0.0186 0.3222 0.030 Uiso calc R H
O6 1 0.58700(10) 0.10211(17) 0.42072(4) 0.0339(3) Uani d . O
C28 1 0.47538(15) 0.1672(3) 0.42980(6) 0.0389(4) Uani d . C
H28A 1 0.4740 0.1616 0.4634 0.058 Uiso calc R H
H28B 1 0.4115 0.0918 0.4131 0.058 Uiso calc R H
H28C 1 0.4642 0.2930 0.4191 0.058 Uiso calc R 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
_geom_angle_publ_flag
O2 N1 O1 122.96(14) ?
O2 N1 C1 118.78(13) ?
O1 N1 C1 118.26(14) ?
C2 C1 C6 121.48(15) ?
C2 C1 N1 118.91(14) ?
C6 C1 N1 119.60(14) ?
C3 C2 C1 119.31(15) ?
C2 C3 C4 120.76(14) ?
C5 C4 C3 118.55(15) ?
C5 C4 N2 116.43(14) ?
C3 C4 N2 125.00(14) ?
C6 C5 C4 121.05(15) ?
C5 C6 C1 118.82(15) ?
C7 N2 C4 120.63(14) yes
N2 C7 C8 121.83(15) yes
C9 C8 C13 118.03(15) ?
C9 C8 C7 120.99(14) ?
C13 C8 C7 120.97(14) ?
C10 C9 C8 121.12(15) ?
C11 C10 C9 119.66(14) ?
O3 C11 C10 124.88(14) ?
O3 C11 C12 115.22(14) ?
C10 C11 C12 119.89(15) ?
C13 C12 C11 119.70(15) ?
C12 C13 C8 121.56(15) ?
C11 O3 C14 117.51(13) ?
O5 N3 O4 123.07(15) ?
O5 N3 C15 118.46(14) ?
O4 N3 C15 118.47(14) ?
C20 C15 C16 122.01(15) ?
C20 C15 N3 119.07(15) ?
C16 C15 N3 118.91(15) ?
C17 C16 C15 118.56(15) ?
C16 C17 C18 120.78(15) ?
C17 C18 C19 119.39(15) ?
C17 C18 N4 122.61(14) ?
C19 C18 N4 117.93(14) ?
C20 C19 C18 120.32(15) ?
C19 C20 C15 118.86(15) ?
C21 N4 C18 118.97(14) yes
N4 C21 C22 122.05(15) yes
C23 C22 C27 118.35(15) ?
C23 C22 C21 120.39(15) ?
C27 C22 C21 121.23(14) ?
C24 C23 C22 121.37(15) ?
C23 C24 C25 119.17(15) ?
O6 C25 C24 125.02(14) ?
O6 C25 C26 114.72(14) ?
C24 C25 C26 120.25(15) ?
C27 C26 C25 120.16(15) ?
C26 C27 C22 120.68(14) ?
C25 O6 C28 117.53(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 N1 1.2334(17) ?
O2 N1 1.2259(17) ?
N1 C1 1.461(2) ?
C1 C2 1.382(2) ?
C1 C6 1.383(2) ?
C2 C3 1.377(2) ?
C3 C4 1.399(2) ?
C4 C5 1.396(2) ?
C4 N2 1.410(2) yes
C5 C6 1.382(2) ?
N2 C7 1.277(2) yes
C7 C8 1.454(2) yes
C8 C9 1.394(2) ?
C8 C13 1.398(2) ?
C9 C10 1.387(2) ?
C10 C11 1.387(2) ?
C11 O3 1.3640(19) ?
C11 C12 1.399(2) ?
C12 C13 1.369(2) ?
O3 C14 1.434(2) ?
O4 N3 1.2252(19) ?
O5 N3 1.2239(17) ?
N3 C15 1.462(2) ?
C15 C20 1.384(2) ?
C15 C16 1.387(2) ?
C16 C17 1.379(2) ?
C17 C18 1.394(2) ?
C18 C19 1.398(2) ?
C18 N4 1.412(2) yes
C19 C20 1.381(2) ?
N4 C21 1.278(2) yes
C21 C22 1.455(2) yes
C22 C23 1.393(2) ?
C22 C27 1.403(2) ?
C23 C24 1.387(2) ?
C24 C25 1.388(2) ?
C25 O6 1.3679(19) ?
C25 C26 1.393(2) ?
C26 C27 1.373(2) ?
O6 C28 1.4307(19) ?
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
_geom_torsion_publ_flag
O2 N1 C1 C2 4.8(2) yes
O1 N1 C1 C2 -175.66(15) yes
O2 N1 C1 C6 -174.08(15) yes
O1 N1 C1 C6 5.5(2) yes
C6 C1 C2 C3 -0.5(3) ?
N1 C1 C2 C3 -179.35(15) ?
C1 C2 C3 C4 1.7(3) ?
C2 C3 C4 C5 -2.0(2) ?
C2 C3 C4 N2 179.90(16) ?
C3 C4 C5 C6 1.0(3) ?
N2 C4 C5 C6 179.26(16) ?
C4 C5 C6 C1 0.2(3) ?
C2 C1 C6 C5 -0.5(3) ?
N1 C1 C6 C5 178.37(15) ?
C5 C4 N2 C7 166.24(16) yes
C3 C4 N2 C7 -15.6(2) yes
C4 N2 C7 C8 177.95(14) yes
N2 C7 C8 C9 178.50(16) yes
N2 C7 C8 C13 -0.5(2) yes
C13 C8 C9 C10 1.7(2) ?
C7 C8 C9 C10 -177.38(15) ?
C8 C9 C10 C11 -0.3(2) ?
C9 C10 C11 O3 178.53(15) ?
C9 C10 C11 C12 -1.4(2) ?
O3 C11 C12 C13 -178.32(15) ?
C10 C11 C12 C13 1.6(2) ?
C11 C12 C13 C8 -0.1(3) ?
C9 C8 C13 C12 -1.5(2) ?
C7 C8 C13 C12 177.59(15) ?
C10 C11 O3 C14 -7.6(2) yes
C12 C11 O3 C14 172.34(15) yes
O5 N3 C15 C20 12.7(2) yes
O4 N3 C15 C20 -166.78(16) yes
O5 N3 C15 C16 -168.10(16) yes
O4 N3 C15 C16 12.4(2) yes
C20 C15 C16 C17 2.0(2) ?
N3 C15 C16 C17 -177.11(14) ?
C15 C16 C17 C18 0.0(2) ?
C16 C17 C18 C19 -2.5(2) ?
C16 C17 C18 N4 -179.29(14) ?
C17 C18 C19 C20 3.0(2) ?
N4 C18 C19 C20 179.97(14) ?
C18 C19 C20 C15 -1.0(2) ?
C16 C15 C20 C19 -1.5(2) ?
N3 C15 C20 C19 177.63(14) ?
C17 C18 N4 C21 -42.2(2) yes
C19 C18 N4 C21 141.01(16) yes
C18 N4 C21 C22 177.50(14) yes
N4 C21 C22 C23 173.34(15) yes
N4 C21 C22 C27 -4.7(2) yes
C27 C22 C23 C24 0.7(2) ?
C21 C22 C23 C24 -177.40(15) ?
C22 C23 C24 C25 0.7(2) ?
C23 C24 C25 O6 179.47(15) ?
C23 C24 C25 C26 -1.5(2) ?
O6 C25 C26 C27 179.84(14) ?
C24 C25 C26 C27 0.7(2) ?
C25 C26 C27 C22 0.8(2) ?
C23 C22 C27 C26 -1.5(2) ?
C21 C22 C27 C26 176.58(15) ?
C24 C25 O6 C28 -4.4(2) yes
C26 C25 O6 C28 176.44(15) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 230214
