#------------------------------------------------------------------------------
#$Date: 2019-09-18 19:21:44 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218477 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/55/7215551.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_7215551
loop_
_publ_author_name
'Imai, Yoshitane'
'Kamon, Kensaku'
'Kido, Shingo'
'Harada, Takunori'
'Tajima, Nobuo'
'Sato, Tomohiro'
'Kuroda, Reiko'
'Matsubara, Yoshio'
_publ_section_title
;
 Formation and crystal structure of the chiral charge-transfer complex
 with axially chiral 1,1'-bis-2-naphthol derivatives and tetracyanobenzene
;
_journal_coden_ASTM              CRECF4
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              620
_journal_page_last               624
_journal_paper_doi               10.1039/b817131a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C21 H11 N4 O'
_chemical_formula_weight         335.34
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 100.479(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.469(3)
_cell_length_b                   7.2740(8)
_cell_length_c                   8.7625(10)
_cell_measurement_reflns_used    3061
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.56
_cell_volume                     1659.0(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'ω scans'
_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    0.0636
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7325
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         1.56
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9621
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3683
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0481
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1068
_refine_ls_wR_factor_ref         0.1238
_reflns_number_gt                3061
_reflns_number_total             3683
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7200505
_cod_data_source_file            b817131a.cif
_cod_data_source_block           imai711_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Updated bibliographic information.

 Antanas Vaitkus,
 2019-09-18

 Marked entry as a duplicate of entry 7200505.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_cell_volume        1658.9(3)
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7215551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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 0.47143(8) 0.7302(3) 0.9931(2) 0.0141(5) Uani 1 1 d .
C2 C 0.44935(8) 0.8156(3) 1.1051(2) 0.0151(5) Uani 1 1 d .
C3 C 0.39559(9) 0.8107(3) 1.0997(3) 0.0185(5) Uani 1 1 d .
H3 H 0.3814 0.8620 1.1823 0.022 Uiso 1 1 calc R
C4 C 0.36411(9) 0.7328(3) 0.9767(3) 0.0183(5) Uani 1 1 d .
H4 H 0.3281 0.7294 0.9744 0.022 Uiso 1 1 calc R
C5 C 0.35214(9) 0.5912(3) 0.7149(3) 0.0176(5) Uani 1 1 d .
H5 H 0.3159 0.5958 0.7085 0.021 Uiso 1 1 calc R
C6 C 0.37153(9) 0.5219(3) 0.5924(3) 0.0196(5) Uani 1 1 d .
C7 C 0.42565(9) 0.5066(3) 0.6077(3) 0.0192(5) Uani 1 1 d .
H7 H 0.4397 0.4537 0.5256 0.023 Uiso 1 1 calc R
C8 C 0.45790(9) 0.5661(3) 0.7376(3) 0.0172(5) Uani 1 1 d .
H8 H 0.4939 0.5517 0.7448 0.021 Uiso 1 1 calc R
C9 C 0.43871(9) 0.6494(3) 0.8629(3) 0.0153(5) Uani 1 1 d .
C10 C 0.38449(8) 0.6566(3) 0.8517(3) 0.0153(5) Uani 1 1 d .
O2 O 0.48105(6) 0.9106(2) 1.21801(18) 0.0201(4) Uani 1 1 d .
H2 H 0.4657 0.9314 1.2922 0.030 Uiso 1 1 calc R
C6M C 0.33741(9) 0.4633(4) 0.4429(3) 0.0240(6) Uani 1 1 d .
H6M1 H 0.3375 0.5588 0.3641 0.036 Uiso 1 1 calc R
H6M2 H 0.3023 0.4449 0.4609 0.036 Uiso 1 1 calc R
H6M3 H 0.3504 0.3480 0.4067 0.036 Uiso 1 1 calc R
C11 C 0.30202(9) 1.1305(3) 0.7614(3) 0.0188(5) Uani 1 1 d .
H11 H 0.2656 1.1243 0.7385 0.023 Uiso 1 1 calc R
C12 C 0.32690(9) 1.2049(3) 0.9010(3) 0.0182(5) Uani 1 1 d .
C13 C 0.38090(9) 1.2109(3) 0.9370(3) 0.0169(5) Uani 1 1 d .
C14 C 0.40979(9) 1.1439(3) 0.8319(3) 0.0176(5) Uani 1 1 d .
H14 H 0.4463 1.1458 0.8563 0.021 Uiso 1 1 calc R
C15 C 0.38490(9) 1.0744(3) 0.6910(3) 0.0168(5) Uani 1 1 d .
C16 C 0.33090(9) 1.0654(3) 0.6560(3) 0.0179(5) Uani 1 1 d .
C17 C 0.29680(9) 1.2782(4) 1.0083(3) 0.0243(6) Uani 1 1 d .
N18 N 0.27277(8) 1.3391(4) 1.0917(3) 0.0367(6) Uani 1 1 d .
C19 C 0.40610(9) 1.2801(3) 1.0860(3) 0.0186(5) Uani 1 1 d .
N20 N 0.42597(8) 1.3308(3) 1.2042(2) 0.0276(5) Uani 1 1 d .
C21 C 0.41333(9) 1.0170(4) 0.5749(3) 0.0206(5) Uani 1 1 d .
N22 N 0.43444(8) 0.9774(3) 0.4770(2) 0.0278(5) Uani 1 1 d .
C23 C 0.30611(9) 0.9885(3) 0.5093(3) 0.0221(5) Uani 1 1 d .
N24 N 0.28672(9) 0.9294(4) 0.3935(3) 0.0318(5) 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_3
C2 C1 C9 118.71(19) .
C2 C1 C1 119.7(2) 2_657
C9 C1 C1 121.5(2) 2_657
O2 C2 C1 117.43(19) .
O2 C2 C3 121.29(19) .
C1 C2 C3 121.2(2) .
C4 C3 C2 120.3(2) .
C3 C4 C10 120.7(2) .
C6 C5 C10 122.0(2) .
C5 C6 C7 118.1(2) .
C5 C6 C6M 122.3(2) .
C7 C6 C6M 119.6(2) .
C8 C7 C6 121.5(2) .
C7 C8 C9 121.4(2) .
C10 C9 C8 117.3(2) .
C10 C9 C1 119.9(2) .
C8 C9 C1 122.7(2) .
C4 C10 C9 118.8(2) .
C4 C10 C5 121.7(2) .
C9 C10 C5 119.4(2) .
C16 C11 C12 119.3(2) .
C11 C12 C13 120.6(2) .
C11 C12 C17 119.3(2) .
C13 C12 C17 120.1(2) .
C14 C13 C12 120.0(2) .
C14 C13 C19 120.2(2) .
C12 C13 C19 119.8(2) .
C15 C14 C13 119.3(2) .
C14 C15 C16 120.7(2) .
C14 C15 C21 120.9(2) .
C16 C15 C21 118.4(2) .
C11 C16 C15 120.0(2) .
C11 C16 C23 120.6(2) .
C15 C16 C23 119.4(2) .
N18 C17 C12 178.8(3) .
N20 C19 C13 178.5(3) .
N22 C21 C15 176.4(3) .
N24 C23 C16 179.4(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.378(3) .
C1 C9 1.427(3) .
C1 C1 1.495(4) 2_657
C2 O2 1.363(3) .
C2 C3 1.416(3) .
C3 C4 1.360(3) .
C4 C10 1.418(3) .
C5 C6 1.368(3) .
C5 C10 1.422(3) .
C6 C7 1.419(3) .
C6 C6M 1.511(3) .
C7 C8 1.363(3) .
C8 C9 1.426(3) .
C9 C10 1.422(3) .
C11 C16 1.385(3) .
C11 C12 1.389(3) .
C12 C13 1.407(3) .
C12 C17 1.441(3) .
C13 C14 1.388(3) .
C13 C19 1.444(3) .
C14 C15 1.385(3) .
C15 C16 1.408(3) .
C15 C21 1.433(3) .
C16 C23 1.445(3) .
C17 N18 1.141(3) .
C19 N20 1.134(3) .
C21 N22 1.142(3) .
C23 N24 1.135(3) .
