#------------------------------------------------------------------------------
#$Date: 2017-08-02 08:00:08 +0300 (Wed, 02 Aug 2017) $
#$Revision: 199455 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228828.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_7228828
loop_
_publ_author_name
'Lei, Hu'
'Langlois, Adam'
'Fortin, Daniel'
'Karsenti, Paul-Ludovic'
'Aly, Shawkat M.'
'Harvey, Pierre D.'
_publ_section_title
;
 Rendering cross-conjugated azophenine derivatives emissive to probe the
 silent photophysical properties of emeraldine
;
_journal_name_full               'Phys. Chem. Chem. Phys.'
_journal_paper_doi               10.1039/C7CP04102K
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C20 H14 Cl2 N2'
_chemical_formula_sum            'C20 H14 Cl2 N2'
_chemical_formula_weight         353.23
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2015-09-02T09:47:38-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2016-07-25 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.451(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2044(5)
_cell_length_b                   6.0526(3)
_cell_length_c                   20.7810(8)
_cell_measurement_reflns_used    9465
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      70.3998
_cell_measurement_theta_min      3.371
_cell_measurement_wavelength     1.54186
_cell_volume                     1713.48(12)
_computing_cell_refinement       'SAINT V8.27B integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_UB_11      -0.636674E-1
_diffrn_orient_matrix_UB_12      -0.283924E-1
_diffrn_orient_matrix_UB_13      -0.34781E-1
_diffrn_orient_matrix_UB_21      0.358462E-1
_diffrn_orient_matrix_UB_22      -0.775225E-1
_diffrn_orient_matrix_UB_23      -0.284686E-1
_diffrn_orient_matrix_UB_31      -0.678478E-2
_diffrn_orient_matrix_UB_32      -0.143146
_diffrn_orient_matrix_UB_33      0.223161E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0688
_diffrn_reflns_av_unetI/netI     0.0754
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8918
_diffrn_reflns_reduction_process
;
 Scaled and merged with Sortav
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        70
_diffrn_reflns_theta_max         70.72
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    3.416
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.867
_refine_diff_density_min         -0.855
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0927
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2664
_refine_ls_wR_factor_ref         0.3147
_reflns_number_gt                1911
_reflns_number_total             3206
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c7cp04102k2.cif
_cod_data_source_block           cu_harvey_2hl80a_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7228828
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 0.9273(4) 1.3715(9) -0.1098(3) 0.0595(14) Uani 1 1 d .
H1 H 0.963 1.4706 -0.1295 0.071 Uiso 1 1 calc R
C2 C 0.8828(3) 1.2483(8) -0.0853(2) 0.0468(11) Uani 1 1 d .
C3 C 0.8303(3) 1.0967(7) -0.0545(2) 0.0406(10) Uani 1 1 d .
C4 C 0.7420(3) 1.1602(7) -0.0435(2) 0.0396(10) Uani 1 1 d .
H4 H 0.7158 1.3029 -0.0568 0.048 Uiso 1 1 calc R
C5 C 0.6919(3) 1.0145(7) -0.01291(19) 0.0393(10) Uani 1 1 d .
H5 H 0.631 1.0579 -0.0064 0.047 Uiso 1 1 calc R
C6 C 0.7298(3) 0.8073(7) 0.00817(19) 0.0365(10) Uani 1 1 d .
C7 C 0.8209(3) 0.7490(7) -0.0008(2) 0.0399(10) Uani 1 1 d .
H7 H 0.8496 0.6105 0.0152 0.048 Uiso 1 1 calc R
C8 C 0.8696(3) 0.8915(7) -0.0328(2) 0.0418(11) Uani 1 1 d .
H8 H 0.9301 0.848 -0.0399 0.05 Uiso 1 1 calc R
C9 C 0.5967(3) 0.5895(7) 0.01965(18) 0.0333(9) Uani 1 1 d .
C10 C 0.5313(3) 0.6418(7) -0.04502(18) 0.0349(9) Uani 1 1 d .
H10 H 0.5529 0.7357 -0.0746 0.042 Uiso 1 1 calc R
C11 C 0.5608(3) 0.4415(7) 0.06421(19) 0.0348(9) Uani 1 1 d .
C12 C 0.6214(3) 0.2490(7) 0.17461(19) 0.0364(10) Uani 1 1 d .
C13 C 0.6550(3) 0.3120(7) 0.24164(19) 0.0375(10) Uani 1 1 d .
H13 H 0.6816 0.4556 0.2528 0.045 Uiso 1 1 calc R
C14 C 0.6501(3) 0.1679(7) 0.2921(2) 0.0379(10) Uani 1 1 d .
H14 H 0.6739 0.2125 0.3376 0.045 Uiso 1 1 calc R
C15 C 0.6105(3) -0.0429(7) 0.2765(2) 0.0391(10) Uani 1 1 d .
C16 C 0.5772(3) -0.1043(7) 0.20869(19) 0.0400(10) Uani 1 1 d .
H16 H 0.5498 -0.247 0.197 0.048 Uiso 1 1 calc R
C17 C 0.5838(3) 0.0394(7) 0.1589(2) 0.0392(10) Uani 1 1 d .
H17 H 0.5622 -0.0061 0.1133 0.047 Uiso 1 1 calc R
C18 C 0.6057(3) -0.1939(7) 0.3285(2) 0.0422(11) Uani 1 1 d .
C19 C 0.6032(4) -0.3168(8) 0.3725(2) 0.0531(13) Uani 1 1 d .
H19 H 0.6011 -0.415 0.4077 0.064 Uiso 1 1 calc R
C20 C 0.3712(6) 0.4691(18) 0.2478(4) 0.140(4) Uani 1 1 d .
H20A H 0.4409 0.4469 0.2732 0.168 Uiso 1 1 calc R
H20B H 0.3307 0.4284 0.2777 0.168 Uiso 1 1 calc R
N1 N 0.6869(2) 0.6585(6) 0.04370(16) 0.0364(8) Uani 1 1 d .
N2 N 0.6287(2) 0.4020(6) 0.12479(15) 0.0396(9) Uani 1 1 d .
H2 H 0.683 0.4807 0.1336 0.048 Uiso 1 1 calc R
Cl1 Cl 0.35228(14) 0.7507(4) 0.22651(10) 0.1084(8) Uani 1 1 d .
Cl2 Cl 0.3430(2) 0.2971(5) 0.18002(13) 0.1364(10) 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 0.0181 0.0091 '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 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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 H1 180 .
C1 C2 C3 178.9(6) .
C8 C3 C4 119.6(4) .
C8 C3 C2 120.3(4) .
C4 C3 C2 120.1(4) .
C3 C4 C5 120.0(4) .
C3 C4 H4 120 .
C5 C4 H4 120 .
C6 C5 C4 120.9(4) .
C6 C5 H5 119.5 .
C4 C5 H5 119.5 .
C5 C6 C7 118.4(4) .
C5 C6 N1 123.9(4) .
C7 C6 N1 117.5(4) .
C8 C7 C6 120.7(4) .
C8 C7 H7 119.6 .
C6 C7 H7 119.6 .
C3 C8 C7 120.3(4) .
C3 C8 H8 119.9 .
C7 C8 H8 119.9 .
N1 C9 C10 126.4(4) .
N1 C9 C11 115.4(3) .
C10 C9 C11 118.2(3) .
C11 C10 C9 120.6(4) 3_665
C11 C10 H10 119.7 3_665
C9 C10 H10 119.7 .
C10 C11 N2 125.1(4) 3_665
C10 C11 C9 121.2(3) 3_665
N2 C11 C9 113.7(3) .
C17 C12 C13 119.3(4) .
C17 C12 N2 122.2(4) .
C13 C12 N2 118.6(4) .
C14 C13 C12 120.7(4) .
C14 C13 H13 119.7 .
C12 C13 H13 119.7 .
C13 C14 C15 120.4(4) .
C13 C14 H14 119.8 .
C15 C14 H14 119.8 .
C14 C15 C16 118.2(4) .
C14 C15 C18 120.8(4) .
C16 C15 C18 120.9(4) .
C17 C16 C15 120.9(4) .
C17 C16 H16 119.6 .
C15 C16 H16 119.6 .
C16 C17 C12 120.5(4) .
C16 C17 H17 119.7 .
C12 C17 H17 119.7 .
C19 C18 C15 178.7(5) .
C18 C19 H19 180 .
Cl2 C20 Cl1 113.5(4) .
Cl2 C20 H20A 108.9 .
Cl1 C20 H20A 108.9 .
Cl2 C20 H20B 108.9 .
Cl1 C20 H20B 108.9 .
H20A C20 H20B 107.7 .
C9 N1 C6 121.9(3) .
C11 N2 C12 127.4(3) .
C11 N2 H2 116.3 .
C12 N2 H2 116.3 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.182(7) .
C1 H1 0.95 .
C2 C3 1.442(6) .
C3 C8 1.383(6) .
C3 C4 1.392(6) .
C4 C5 1.393(6) .
C4 H4 0.95 .
C5 C6 1.386(6) .
C5 H5 0.95 .
C6 C7 1.404(6) .
C6 N1 1.408(5) .
C7 C8 1.387(6) .
C7 H7 0.95 .
C8 H8 0.95 .
C9 N1 1.304(5) .
C9 C10 1.436(5) .
C9 C11 1.480(6) .
C10 C11 1.352(5) 3_665
C10 H10 0.95 .
C11 C10 1.352(5) 3_665
C11 N2 1.373(5) .
C12 C17 1.380(6) .
C12 C13 1.392(6) .
C12 N2 1.414(5) .
C13 C14 1.380(6) .
C13 H13 0.95 .
C14 C15 1.395(6) .
C14 H14 0.95 .
C15 C16 1.404(6) .
C15 C18 1.430(6) .
C16 C17 1.375(6) .
C16 H16 0.95 .
C17 H17 0.95 .
C18 C19 1.188(6) .
C19 H19 0.95 .
C20 Cl2 1.705(10) .
C20 Cl1 1.763(11) .
C20 H20A 0.99 .
C20 H20B 0.99 .
N2 H2 0.88 .
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_1
_geom_torsion_site_symmetry_4
C1 C2 C3 C8 -4E1(3) . .
C1 C2 C3 C4 14E1(3) . .
C8 C3 C4 C5 -2.3(6) . .
C2 C3 C4 C5 -179.2(4) . .
C3 C4 C5 C6 1.4(6) . .
C4 C5 C6 C7 1.2(6) . .
C4 C5 C6 N1 175.2(4) . .
C5 C6 C7 C8 -3.0(6) . .
N1 C6 C7 C8 -177.3(3) . .
C4 C3 C8 C7 0.5(6) . .
C2 C3 C8 C7 177.5(4) . .
C6 C7 C8 C3 2.1(6) . .
N1 C9 C10 C11 179.7(4) . 3_665
C11 C9 C10 C11 0.4(6) . 3_665
N1 C9 C11 C10 -179.8(4) . 3_665
C10 C9 C11 C10 -0.5(6) . 3_665
N1 C9 C11 N2 0.7(5) . .
C10 C9 C11 N2 -180.0(4) . .
C17 C12 C13 C14 -0.6(6) . .
N2 C12 C13 C14 -179.5(4) . .
C12 C13 C14 C15 -0.6(6) . .
C13 C14 C15 C16 0.8(6) . .
C13 C14 C15 C18 179.5(4) . .
C14 C15 C16 C17 0.2(6) . .
C18 C15 C16 C17 -178.6(4) . .
C15 C16 C17 C12 -1.4(6) . .
C13 C12 C17 C16 1.6(6) . .
N2 C12 C17 C16 -179.5(4) . .
C14 C15 C18 C19 -2E1(2) . .
C16 C15 C18 C19 16E1(2) . .
C10 C9 N1 C6 3.3(6) . .
C11 C9 N1 C6 -177.4(4) . .
C5 C6 N1 C9 57.7(5) . .
C7 C6 N1 C9 -128.3(4) . .
C10 C11 N2 C12 8.6(7) 3_665 .
C9 C11 N2 C12 -171.9(4) . .
C17 C12 N2 C11 41.4(6) . .
C13 C12 N2 C11 -139.7(4) . .
