#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/27/1502745.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_1502745
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           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 90.594(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.3408(18)
_cell_length_b                   3.8902(4)
_cell_length_c                   20.2120(19)
_cell_measurement_reflns_used    5282
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      28.046
_cell_measurement_theta_min      2.900
_cell_volume                     1520.7(3)
_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 0.914
_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  0.0268
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            9841
_diffrn_reflns_theta_full        26.60
_diffrn_reflns_theta_max         28.21
_diffrn_reflns_theta_min         1.46
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  699
_diffrn_standards_number         144
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9950
_exptl_absorpt_correction_T_min  0.8698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.929
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.929
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0968P)²+0.5043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1347
_refine_ls_wR_factor_ref         0.1416
_reflns_number_gt                2927
_reflns_number_total             3419
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jp907441p_si_002.cif
_cod_data_source_block           sono1b
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      P2(1)/n
_cod_database_code               1502745
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_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 0.23137(7) -0.0065(4) 0.97209(7) 0.0328(3) Uani 1 1 d .
C2 C 0.17377(7) -0.0664(4) 0.93204(9) 0.0421(4) Uani 1 1 d .
H2 H 0.1336 -0.1690 0.9501 0.051 Uiso 1 1 calc R
C3 C 0.17499(8) 0.0224(5) 0.86656(9) 0.0485(4) Uani 1 1 d .
H3 H 0.1355 -0.0144 0.8391 0.058 Uiso 1 1 calc R
C4 C 0.23432(9) 0.1665(4) 0.84063(8) 0.0470(4) Uani 1 1 d .
H4 H 0.2353 0.2316 0.7954 0.056 Uiso 1 1 calc R
C5 C 0.29231(8) 0.2162(4) 0.88042(7) 0.0383(3) Uani 1 1 d .
H5 H 0.3329 0.3093 0.8613 0.046 Uiso 1 1 calc R
C6 C 0.29304(6) 0.1337(3) 0.94787(6) 0.0299(3) Uani 1 1 d .
C7 C 0.35660(6) 0.1767(3) 0.98743(6) 0.0299(3) Uani 1 1 d .
H7 H 0.3603 0.0536 1.0279 0.036 Uiso 1 1 calc R
C8 C 0.40988(6) 0.3784(3) 0.97026(6) 0.0301(3) Uani 1 1 d .
H8 H 0.4057 0.5129 0.9312 0.036 Uiso 1 1 calc R
C9 C 0.47290(6) 0.3999(3) 1.00835(6) 0.0304(3) Uani 1 1 d .
H9 H 0.4767 0.2658 1.0475 0.036 Uiso 1 1 calc R
C10 C 0.46700(8) 0.8452(4) 0.22788(6) 0.0347(3) Uani 1 1 d .
C11 C 0.42817(9) 0.7299(4) 0.17412(7) 0.0471(4) Uani 1 1 d .
H11 H 0.4460 0.7461 0.1306 0.057 Uiso 1 1 calc R
C12 C 0.36394(11) 0.5927(5) 0.18431(9) 0.0557(5) Uani 1 1 d .
H12 H 0.3374 0.5071 0.1481 0.067 Uiso 1 1 calc R
C13 C 0.33809(9) 0.5797(4) 0.24767(10) 0.0520(4) Uani 1 1 d .
H13 H 0.2937 0.4834 0.2549 0.062 Uiso 1 1 calc R
C14 C 0.37621(8) 0.7056(4) 0.30084(8) 0.0405(3) Uani 1 1 d .
H14 H 0.3566 0.7015 0.3437 0.049 Uiso 1 1 calc R
C15 C 0.44273(7) 0.8383(3) 0.29300(6) 0.0310(3) Uani 1 1 d .
C16 C 0.48148(7) 0.9777(4) 0.34985(6) 0.0309(3) Uani 1 1 d .
H16 H 0.5172 1.1392 0.3414 0.037 Uiso 1 1 calc R
C17 C 0.46951(7) 0.8908(3) 0.41296(6) 0.0307(3) Uani 1 1 d .
H17 H 0.4353 0.7217 0.4216 0.037 Uiso 1 1 calc R
C18 C 0.50596(7) 1.0411(4) 0.46816(6) 0.0308(3) Uani 1 1 d .
H18 H 0.5405 1.2081 0.4592 0.037 Uiso 1 1 calc R
N1 N 0.22296(6) -0.0913(3) 1.04238(7) 0.0406(3) Uani 1 1 d .
N2 N 0.53651(7) 0.9703(4) 0.21339(5) 0.0409(3) Uani 1 1 d .
O1 O 0.25922(6) 0.0514(4) 1.08385(6) 0.0579(4) Uani 1 1 d .
O2 O 0.17757(7) -0.2950(4) 1.05702(7) 0.0694(4) Uani 1 1 d .
O3 O 0.58352(6) 0.9104(4) 0.25247(5) 0.0586(4) Uani 1 1 d .
O4 O 0.54506(7) 1.1268(4) 0.16151(6) 0.0624(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 122.73(14) .
C2 C1 N1 115.43(13) .
C6 C1 N1 121.82(12) .
C3 C2 C1 119.95(14) .
C3 C2 H2 120.0 .
C1 C2 H2 120.0 .
C2 C3 C4 119.40(13) .
C2 C3 H3 120.3 .
C4 C3 H3 120.3 .
C3 C4 C5 120.35(15) .
C3 C4 H4 119.8 .
C5 C4 H4 119.8 .
C4 C5 C6 122.17(14) .
C4 C5 H5 118.9 .
C6 C5 H5 118.9 .
C1 C6 C5 115.36(12) .
C1 C6 C7 124.30(12) .
C5 C6 C7 120.24(12) .
C8 C7 C6 124.44(12) .
C8 C7 H7 117.8 .
C6 C7 H7 117.8 .
C7 C8 C9 122.95(12) .
C7 C8 H8 118.5 .
C9 C8 H8 118.5 .
C9 C9 C8 123.73(16) 3_667
C9 C9 H9 118.1 3_667
C8 C9 H9 118.1 .
C11 C10 C15 123.00(15) .
C11 C10 N2 116.20(13) .
C15 C10 N2 120.79(12) .
C12 C11 C10 119.48(16) .
C12 C11 H11 120.3 .
C10 C11 H11 120.3 .
C11 C12 C13 119.43(14) .
C11 C12 H12 120.3 .
C13 C12 H12 120.3 .
C12 C13 C14 120.77(17) .
C12 C13 H13 119.6 .
C14 C13 H13 119.6 .
C13 C14 C15 121.71(15) .
C13 C14 H14 119.1 .
C15 C14 H14 119.1 .
C14 C15 C10 115.54(12) .
C14 C15 C16 120.72(12) .
C10 C15 C16 123.64(13) .
C17 C16 C15 123.97(13) .
C17 C16 H16 118.0 .
C15 C16 H16 118.0 .
C16 C17 C18 123.16(13) .
C16 C17 H17 118.4 .
C18 C17 H17 118.4 .
C18 C18 C17 123.84(17) 3_676
C18 C18 H18 118.1 3_676
C17 C18 H18 118.1 .
O1 N1 O2 122.55(14) .
O1 N1 C1 119.55(12) .
O2 N1 C1 117.84(13) .
O3 N2 O4 122.85(14) .
O3 N2 C10 119.15(12) .
O4 N2 C10 117.99(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3899(19) .
C1 C6 1.4043(19) .
C1 N1 1.4692(19) .
C2 C3 1.368(2) .
C2 H2 0.9500 .
C3 C4 1.385(3) .
C3 H3 0.9500 .
C4 C5 1.387(2) .
C4 H4 0.9500 .
C5 C6 1.400(2) .
C5 H5 0.9500 .
C6 C7 1.4691(17) .
C7 C8 1.3437(18) .
C7 H7 0.9500 .
C8 C9 1.4374(18) .
C8 H8 0.9500 .
C9 C9 1.351(3) 3_667
C9 H9 0.9500 .
C10 C11 1.3890(19) .
C10 C15 1.4022(18) .
C10 N2 1.462(2) .
C11 C12 1.370(3) .
C11 H11 0.9500 .
C12 C13 1.380(3) .
C12 H12 0.9500 .
C13 C14 1.386(2) .
C13 H13 0.9500 .
C14 C15 1.397(2) .
C14 H14 0.9500 .
C15 C16 1.4691(17) .
C16 C17 1.3421(18) .
C16 H16 0.9500 .
C17 C18 1.4379(18) .
C17 H17 0.9500 .
C18 C18 1.348(3) 3_676
C18 H18 0.9500 .
N1 O1 1.2207(18) .
N1 O2 1.2212(17) .
N2 O3 1.2206(16) .
N2 O4 1.2252(16) .
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 -2.1(2) .
N1 C1 C2 C3 176.28(14) .
C1 C2 C3 C4 1.1(2) .
C2 C3 C4 C5 0.8(3) .
C3 C4 C5 C6 -1.8(2) .
C2 C1 C6 C5 1.2(2) .
N1 C1 C6 C5 -177.13(13) .
C2 C1 C6 C7 -175.19(13) .
N1 C1 C6 C7 6.5(2) .
C4 C5 C6 C1 0.8(2) .
C4 C5 C6 C7 177.32(14) .
C1 C6 C7 C8 -163.92(13) .
C5 C6 C7 C8 19.9(2) .
C6 C7 C8 C9 -176.47(12) .
C7 C8 C9 C9 179.67(16) 3_667
C15 C10 C11 C12 -2.0(2) .
N2 C10 C11 C12 176.67(14) .
C10 C11 C12 C13 1.7(2) .
C11 C12 C13 C14 0.4(2) .
C12 C13 C14 C15 -2.3(2) .
C13 C14 C15 C10 2.0(2) .
C13 C14 C15 C16 178.55(14) .
C11 C10 C15 C14 0.2(2) .
N2 C10 C15 C14 -178.47(13) .
C11 C10 C15 C16 -176.28(13) .
N2 C10 C15 C16 5.1(2) .
C14 C15 C16 C17 23.4(2) .
C10 C15 C16 C17 -160.32(13) .
C15 C16 C17 C18 -177.21(12) .
C16 C17 C18 C18 179.32(16) 3_676
C2 C1 N1 O1 -155.63(14) .
C6 C1 N1 O1 22.8(2) .
C2 C1 N1 O2 21.7(2) .
C6 C1 N1 O2 -159.90(14) .
C11 C10 N2 O3 -142.61(15) .
C15 C10 N2 O3 36.1(2) .
C11 C10 N2 O4 36.2(2) .
C15 C10 N2 O4 -145.09(15) .
