#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:29:18 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180396 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/65/7206556.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_7206556
loop_
_publ_author_name
'Mallet, Charlotte'
'Allain, Magali'
'Leriche, Philippe'
'Frère, Pierre'
_publ_section_title
;
 Competition between π--π or furan--perfluorophenyl stacking
 interactions in conjugated compounds prepared from azomethine
 connections
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              5833
_journal_paper_doi               10.1039/c1ce05575e
_journal_volume                  13
_journal_year                    2011
_chemical_formula_moiety         'C18 H14 N2 O1'
_chemical_formula_sum            'C18 H14 N2 O'
_chemical_formula_weight         274.31
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_audit_creation_date             2011-02-24T18:29:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 97.04(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.930(8)
_cell_length_b                   6.041(2)
_cell_length_c                   7.424(1)
_cell_measurement_reflns_used    1776
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.05
_cell_measurement_theta_min      3.43
_cell_volume                     1421.2(6)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND 3.2d (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7548
_diffrn_reflns_theta_full        28.05
_diffrn_reflns_theta_max         28.05
_diffrn_reflns_theta_min         3.43
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.553
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
'(SADABS (Sheldrick, Bruker, 2000))'
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.211
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         1644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0239P)²+1.0622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                971
_reflns_number_total             1644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05575e.txt
_cod_data_source_block           compound1
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7206556
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_calc_flag
_atom_site_refinement_flags
C1 C 0.48024(6) 0.3799(4) 0.6970(3) 0.0399(5) Uani 1 d .
C2 C 0.46915(6) 0.1648(3) 0.6690(3) 0.0359(5) Uani 1 d .
C3 C 0.43044(6) 0.0730(3) 0.5785(3) 0.0372(5) Uani 1 d .
C4 C 0.37913(6) -0.1864(3) 0.4912(3) 0.0343(5) Uani 1 d .
C5 C 0.37339(7) -0.3808(3) 0.3904(3) 0.0408(5) Uani 1 d .
C6 C 0.33347(8) -0.4445(4) 0.3160(3) 0.0503(6) Uani 1 d .
C7 C 0.29889(8) -0.3155(4) 0.3418(3) 0.0537(7) Uani 1 d .
C8 C 0.30404(7) -0.1236(4) 0.4422(3) 0.0479(6) Uani 1 d .
C9 C 0.34399(7) -0.0584(4) 0.5171(3) 0.0401(5) Uani 1 d .
N1 N 0.42068(5) -0.1315(3) 0.5720(2) 0.0368(4) Uani 1 d .
O1 O 0.5 0.0267(3) 0.75 0.0358(5) Uani 1 d S
H1 H 0.4640(7) 0.503(4) 0.652(3) 0.048(6) Uiso 1 d .
H3 H 0.4118(6) 0.187(3) 0.521(3) 0.041(6) Uiso 1 d .
H5 H 0.3978(7) -0.473(3) 0.374(3) 0.041(6) Uiso 1 d .
H6 H 0.3308(7) -0.578(4) 0.247(3) 0.054(7) Uiso 1 d .
H7 H 0.2722(7) -0.365(4) 0.294(3) 0.064(7) Uiso 1 d .
H8 H 0.2797(8) -0.029(4) 0.464(3) 0.063(8) Uiso 1 d .
H9 H 0.3475(6) 0.074(3) 0.597(3) 0.046(6) Uiso 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0368(11) 0.0322(11) 0.0510(13) 0.0062(9) 0.0063(9) 0.0034(9)
C2 0.0318(11) 0.0339(12) 0.0413(11) 0.0045(9) 0.0024(8) 0.0031(9)
C3 0.0355(12) 0.0336(12) 0.0417(12) 0.0044(9) 0.0016(9) 0.0027(9)
C4 0.0349(11) 0.0329(11) 0.0342(10) 0.0053(8) 0.0007(9) 0.0009(9)
C5 0.0479(13) 0.0350(12) 0.0400(12) 0.0015(9) 0.0078(10) 0.0005(10)
C6 0.0610(16) 0.0483(15) 0.0414(13) -0.0057(10) 0.0057(11) -0.0152(12)
C7 0.0428(14) 0.0740(18) 0.0425(13) -0.0010(12) -0.0027(11) -0.0195(14)
C8 0.0363(12) 0.0620(16) 0.0451(13) 0.0017(11) 0.0035(10) -0.0028(12)
C9 0.0392(12) 0.0410(13) 0.0392(12) -0.0009(9) 0.0012(9) 0.0019(10)
N1 0.0342(9) 0.0345(10) 0.0407(10) 0.0004(7) 0.0009(8) 0.0038(8)
O1 0.0327(11) 0.0313(11) 0.0415(11) 0 -0.0026(9) 0
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 0 '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 0.006 '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
_geom_angle_site_symmetry_3
C2 C1 C1 106.62(12) . 2_656
C2 C1 H1 125.3(13) . .
C1 C1 H1 128.1(13) 2_656 .
C1 C2 O1 110.81(17) . .
C1 C2 C3 129.20(18) . .
O1 C2 C3 119.91(17) . .
N1 C3 C2 125.60(18) . .
N1 C3 H3 122.5(11) . .
C2 C3 H3 111.9(11) . .
C5 C4 C9 119.09(19) . .
C5 C4 N1 118.46(18) . .
C9 C4 N1 122.37(18) . .
C6 C5 C4 120.3(2) . .
C6 C5 H5 120.0(12) . .
C4 C5 H5 119.7(12) . .
C5 C6 C7 120.0(2) . .
C5 C6 H6 117.9(14) . .
C7 C6 H6 122.1(14) . .
C8 C7 C6 120.3(2) . .
C8 C7 H7 121.5(15) . .
C6 C7 H7 118.1(15) . .
C7 C8 C9 120.0(2) . .
C7 C8 H8 121.9(14) . .
C9 C8 H8 118.1(14) . .
C8 C9 C4 120.2(2) . .
C8 C9 H9 120.1(12) . .
C4 C9 H9 119.6(12) . .
C3 N1 C4 116.90(16) . .
C2 O1 C2 105.1(2) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.357(3) .
C1 C1 1.403(4) 2_656
C1 H1 0.94(2) .
C2 O1 1.372(2) .
C2 C3 1.443(3) .
C3 N1 1.274(3) .
C3 H3 0.98(2) .
C4 C5 1.393(3) .
C4 C9 1.396(3) .
C4 N1 1.426(2) .
C5 C6 1.380(3) .
C5 H5 0.98(2) .
C6 C7 1.384(3) .
C6 H6 0.95(2) .
C7 C8 1.377(3) .
C7 H7 0.93(2) .
C8 C9 1.385(3) .
C8 H8 0.99(2) .
C9 H9 0.99(2) .
O1 C2 1.372(2) 2_656
