#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/27/1502746.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_1502746
loop_
_publ_author_name
'Sonoda, Yoriko'
'Tsuzuki, Seiji'
'Goto, Midori'
'Tohnai, Norimitsu'
'Yoshida, Masaru'
_publ_section_title
;
 Fluorescence spectroscopic properties of nitro-substituted
 diphenylpolyenes: effects of intramolecular planarization and
 intermolecular interactions in crystals.
;
_journal_issue                   1
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              172
_journal_page_last               182
_journal_paper_doi               10.1021/jp907441p
_journal_volume                  114
_journal_year                    2010
_chemical_formula_sum            'C18 H14 N2 O4'
_chemical_formula_weight         322.31
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.847(3)
_cell_angle_beta                 98.976(3)
_cell_angle_gamma                103.827(3)
_cell_formula_units_Z            2
_cell_length_a                   6.3063(10)
_cell_length_b                   10.8492(17)
_cell_length_c                   12.374(2)
_cell_measurement_reflns_used    1943
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      3.183
_cell_volume                     758.1(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating unit'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4485
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         1.78
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1009
_diffrn_standards_number         35
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9929
_exptl_absorpt_correction_T_min  0.9702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3230
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0482
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0717P)²+0.1726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2442
_reflns_number_total             3230
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp907441p_si_003.cif
_cod_data_source_block           sono2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        758.0(2)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1502746
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.4666(3) 0.60221(16) 0.64147(13) 0.0309(4) Uani 1 1 d .
C2 C 0.6946(3) 0.63711(18) 0.68965(15) 0.0364(4) Uani 1 1 d .
H2 H 0.7602 0.5732 0.7073 0.044 Uiso 1 1 calc R
C3 C 0.8244(3) 0.76852(19) 0.71141(16) 0.0392(4) Uani 1 1 d .
H3 H 0.9819 0.7963 0.7453 0.047 Uiso 1 1 calc R
C4 C 0.7256(3) 0.85973(17) 0.68394(14) 0.0349(4) Uani 1 1 d .
H4 H 0.8173 0.9497 0.6998 0.042 Uiso 1 1 calc R
C5 C 0.4947(3) 0.82320(16) 0.63352(13) 0.0300(4) Uani 1 1 d .
C6 C 0.3639(3) 0.69062(16) 0.61259(13) 0.0302(3) Uani 1 1 d .
H6 H 0.2063 0.6618 0.5789 0.036 Uiso 1 1 calc R
C7 C 0.4004(3) 0.92422(16) 0.60519(14) 0.0327(4) Uani 1 1 d .
H7 H 0.5012 1.0134 0.6282 0.039 Uiso 1 1 calc R
C8 C 0.1878(3) 0.90399(16) 0.55040(14) 0.0316(4) Uani 1 1 d .
H8 H 0.0839 0.8154 0.5259 0.038 Uiso 1 1 calc R
C9 C 0.1072(3) 1.00944(16) 0.52645(14) 0.0326(4) Uani 1 1 d .
H9 H 0.2122 1.0974 0.5495 0.039 Uiso 1 1 calc R
C10 C 1.1786(3) 0.66924(16) 0.02443(15) 0.0335(4) Uani 1 1 d .
C11 C 1.2534(3) 0.63878(17) 0.12089(16) 0.0391(4) Uani 1 1 d .
H11 H 1.3624 0.5917 0.1219 0.047 Uiso 1 1 calc R
C12 C 1.1640(3) 0.67921(19) 0.21633(16) 0.0429(4) Uani 1 1 d .
H12 H 1.2112 0.6597 0.2843 0.051 Uiso 1 1 calc R
C13 C 1.0064(3) 0.74780(18) 0.21318(15) 0.0388(4) Uani 1 1 d .
H13 H 0.9443 0.7729 0.2788 0.047 Uiso 1 1 calc R
C14 C 0.9358(3) 0.78134(16) 0.11671(14) 0.0333(4) Uani 1 1 d .
C15 C 1.0244(3) 0.73970(16) 0.01967(15) 0.0335(4) Uani 1 1 d .
H15 H 0.9791 0.7596 -0.0483 0.040 Uiso 1 1 calc R
C16 C 0.7778(3) 0.86117(18) 0.11944(15) 0.0380(4) Uani 1 1 d .
H16 H 0.7243 0.8845 0.1883 0.046 Uiso 1 1 calc R
C17 C 0.7008(3) 0.90465(17) 0.03581(16) 0.0380(4) Uani 1 1 d .
H17 H 0.7541 0.8836 -0.0333 0.046 Uiso 1 1 calc R
C18 C 0.5430(3) 0.98093(18) 0.04291(16) 0.0387(4) Uani 1 1 d .
H18 H 0.4962 1.0062 0.1137 0.046 Uiso 1 1 calc R
N1 N 0.3239(3) 0.46400(14) 0.62136(12) 0.0360(3) Uani 1 1 d .
N2 N 1.2655(3) 0.62489(15) -0.08042(14) 0.0406(4) Uani 1 1 d .
O1 O 0.4152(2) 0.38244(13) 0.63822(13) 0.0534(4) Uani 1 1 d .
O2 O 0.1203(2) 0.43792(13) 0.58914(13) 0.0499(4) Uani 1 1 d .
O3 O 1.4051(3) 0.56529(17) -0.07686(14) 0.0642(5) Uani 1 1 d .
O4 O 1.1930(3) 0.64942(17) -0.16601(13) 0.0608(4) Uani 1 1 d .
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_site_symmetry_1
C2 C1 C6 123.36(16) .
C2 C1 N1 118.53(14) .
C6 C1 N1 118.10(15) .
C1 C2 C3 117.68(15) .
C1 C2 H2 121.2 .
C3 C2 H2 121.2 .
C2 C3 C4 120.21(16) .
C2 C3 H3 119.9 .
C4 C3 H3 119.9 .
C3 C4 C5 121.87(16) .
C3 C4 H4 119.1 .
C5 C4 H4 119.1 .
C6 C5 C4 117.68(14) .
C6 C5 C7 123.05(15) .
C4 C5 C7 119.27(15) .
C1 C6 C5 119.19(15) .
C1 C6 H6 120.4 .
C5 C6 H6 120.4 .
C8 C7 C5 126.97(15) .
C8 C7 H7 116.5 .
C5 C7 H7 116.5 .
C7 C8 C9 123.67(16) .
C7 C8 H8 118.2 .
C9 C8 H8 118.2 .
C9 C9 C8 124.0(2) 2_576
C9 C9 H9 118.0 2_576
C8 C9 H9 118.0 .
C11 C10 C15 123.40(16) .
C11 C10 N2 119.31(14) .
C15 C10 N2 117.28(15) .
C10 C11 C12 117.57(15) .
C10 C11 H11 121.2 .
C12 C11 H11 121.2 .
C13 C12 C11 120.25(17) .
C13 C12 H12 119.9 .
C11 C12 H12 119.9 .
C12 C13 C14 121.93(16) .
C12 C13 H13 119.0 .
C14 C13 H13 119.0 .
C13 C14 C15 118.00(15) .
C13 C14 C16 120.25(15) .
C15 C14 C16 121.73(16) .
C10 C15 C14 118.82(16) .
C10 C15 H15 120.6 .
C14 C15 H15 120.6 .
C17 C16 C14 127.16(16) .
C17 C16 H16 116.4 .
C14 C16 H16 116.4 .
C16 C17 C18 124.58(17) .
C16 C17 H17 117.7 .
C18 C17 H17 117.7 .
C18 C18 C17 124.8(2) 2_675
C18 C18 H18 117.6 2_675
C17 C18 H18 117.6 .
O1 N1 O2 123.49(15) .
O1 N1 C1 118.38(15) .
O2 N1 C1 118.13(13) .
O3 N2 O4 123.39(16) .
O3 N2 C10 118.18(16) .
O4 N2 C10 118.42(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.378(2) .
C1 C6 1.379(2) .
C1 N1 1.475(2) .
C2 C3 1.383(3) .
C2 H2 0.9500 .
C3 C4 1.385(2) .
C3 H3 0.9500 .
C4 C5 1.399(2) .
C4 H4 0.9500 .
C5 C6 1.398(2) .
C5 C7 1.470(2) .
C6 H6 0.9500 .
C7 C8 1.338(2) .
C7 H7 0.9500 .
C8 C9 1.447(2) .
C8 H8 0.9500 .
C9 C9 1.345(3) 2_576
C9 H9 0.9500 .
C10 C11 1.377(2) .
C10 C15 1.378(2) .
C10 N2 1.476(2) .
C11 C12 1.383(3) .
C11 H11 0.9500 .
C12 C13 1.379(2) .
C12 H12 0.9500 .
C13 C14 1.391(2) .
C13 H13 0.9500 .
C14 C15 1.398(2) .
C14 C16 1.466(2) .
C15 H15 0.9500 .
C16 C17 1.335(3) .
C16 H16 0.9500 .
C17 C18 1.435(2) .
C17 H17 0.9500 .
C18 C18 1.338(4) 2_675
C18 H18 0.9500 .
N1 O1 1.2156(18) .
N1 O2 1.2181(19) .
N2 O3 1.2134(18) .
N2 O4 1.217(2) .
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_site_symmetry_4
C6 C1 C2 C3 1.1(2) .
N1 C1 C2 C3 -177.91(14) .
C1 C2 C3 C4 -0.6(3) .
C2 C3 C4 C5 -0.3(3) .
C3 C4 C5 C6 0.8(2) .
C3 C4 C5 C7 -179.32(15) .
C2 C1 C6 C5 -0.6(2) .
N1 C1 C6 C5 178.42(13) .
C4 C5 C6 C1 -0.4(2) .
C7 C5 C6 C1 179.72(14) .
C6 C5 C7 C8 -4.6(3) .
C4 C5 C7 C8 175.46(16) .
C5 C7 C8 C9 179.48(14) .
C7 C8 C9 C9 -178.61(19) 2_576
C15 C10 C11 C12 1.4(3) .
N2 C10 C11 C12 -178.47(16) .
C10 C11 C12 C13 -0.2(3) .
C11 C12 C13 C14 -1.5(3) .
C12 C13 C14 C15 1.9(3) .
C12 C13 C14 C16 -176.46(17) .
C11 C10 C15 C14 -0.9(3) .
N2 C10 C15 C14 178.96(15) .
C13 C14 C15 C10 -0.8(2) .
C16 C14 C15 C10 177.60(15) .
C13 C14 C16 C17 177.70(19) .
C15 C14 C16 C17 -0.6(3) .
C14 C16 C17 C18 178.99(17) .
C16 C17 C18 C18 -176.6(2) 2_675
C2 C1 N1 O1 -6.5(2) .
C6 C1 N1 O1 174.50(15) .
C2 C1 N1 O2 173.25(15) .
C6 C1 N1 O2 -5.8(2) .
C11 C10 N2 O3 -1.7(2) .
C15 C10 N2 O3 178.43(16) .
C11 C10 N2 O4 178.01(17) .
C15 C10 N2 O4 -1.9(2) .
