#------------------------------------------------------------------------------
#$Date: 2019-09-18 19:11:08 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/05/7200504.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_7200504
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            'C20 H8 Br N4 O'
_chemical_formula_weight         400.21
_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                 101.072(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   26.349(4)
_cell_length_b                   7.3596(11)
_cell_length_c                   8.8067(13)
_cell_measurement_reflns_used    3429
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      1.58
_cell_volume                     1676.0(4)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0603
_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            7309
_diffrn_reflns_theta_full        27.88
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.58
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  0.7903
_exptl_absorpt_correction_T_min  0.3189
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             796
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0275
_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)+(0.0000P)²+0.1458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0577
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                3429
_reflns_number_total             3752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B817131A.txt
_cod_data_source_block           imai711_1
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               7200504
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.47147(9) 0.7302(3) 0.9921(3) 0.0124(5) Uani 1 1 d . . .
C2 C 0.44919(10) 0.8143(4) 1.1030(3) 0.0141(5) Uani 1 1 d . . .
C3 C 0.39535(10) 0.8100(4) 1.0957(3) 0.0162(6) Uani 1 1 d . . .
H3 H 0.3810 0.8599 1.1776 0.019 Uiso 1 1 calc R . .
C4 C 0.36367(11) 0.7340(4) 0.9706(3) 0.0155(6) Uani 1 1 d . . .
H4 H 0.3274 0.7316 0.9662 0.019 Uiso 1 1 calc R . .
C5 C 0.35163(10) 0.5951(4) 0.7105(3) 0.0152(6) Uani 1 1 d . . .
H5 H 0.3151 0.6008 0.7005 0.018 Uiso 1 1 calc R . .
C6 C 0.37282(10) 0.5263(4) 0.5945(3) 0.0161(6) Uani 1 1 d . . .
C7 C 0.42650(10) 0.5081(3) 0.6073(3) 0.0161(6) Uani 1 1 d . . .
H7 H 0.4404 0.4550 0.5258 0.019 Uiso 1 1 calc R . .
C8 C 0.45856(10) 0.5679(3) 0.7388(3) 0.0148(5) Uani 1 1 d . . .
H8 H 0.4949 0.5534 0.7485 0.018 Uiso 1 1 calc R . .
C9 C 0.43891(10) 0.6511(4) 0.8614(3) 0.0129(5) Uani 1 1 d . . .
C10 C 0.38441(10) 0.6588(4) 0.8476(3) 0.0135(6) Uani 1 1 d . . .
O2 O 0.48097(7) 0.9061(2) 1.2173(2) 0.0170(5) Uani 1 1 d . . .
H2 H 0.4655 0.9252 1.2908 0.026 Uiso 1 1 calc R . .
Br6 Br 0.329965(9) 0.44855(5) 0.40649(3) 0.02015(8) Uani 1 1 d . . .
C11 C 0.30159(11) 1.1349(4) 0.7507(3) 0.0170(6) Uani 1 1 d . . .
H11 H 0.2649 1.1317 0.7267 0.020 Uiso 1 1 calc R . .
C12 C 0.32695(10) 1.2064(4) 0.8904(3) 0.0163(6) Uani 1 1 d . . .
C13 C 0.38138(11) 1.2080(4) 0.9277(3) 0.0143(6) Uani 1 1 d . . .
C14 C 0.41007(11) 1.1417(4) 0.8234(3) 0.0165(6) Uani 1 1 d . . .
H14 H 0.4468 1.1427 0.8480 0.020 Uiso 1 1 calc R . .
C15 C 0.38426(10) 1.0736(4) 0.6823(3) 0.0159(6) Uani 1 1 d . . .
C16 C 0.33022(11) 1.0682(3) 0.6464(3) 0.0155(6) Uani 1 1 d . . .
C17 C 0.29650(11) 1.2818(4) 0.9966(3) 0.0204(6) Uani 1 1 d . . .
N18 N 0.27190(10) 1.3426(4) 1.0761(3) 0.0310(6) Uani 1 1 d . . .
C19 C 0.40766(11) 1.2757(4) 1.0763(3) 0.0168(6) Uani 1 1 d . . .
N20 N 0.42914(10) 1.3246(4) 1.1943(3) 0.0249(6) Uani 1 1 d . . .
C21 C 0.41303(10) 1.0146(4) 0.5675(3) 0.0192(6) Uani 1 1 d . . .
N22 N 0.43418(8) 0.9737(5) 0.4715(2) 0.0254(6) Uani 1 1 d . . .
C23 C 0.30432(10) 0.9956(3) 0.4989(3) 0.0183(7) Uani 1 1 d . . .
N24 N 0.28487(8) 0.9397(5) 0.3817(3) 0.0276(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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C2 C1 C9 119.0(2) . . ?
C2 C1 C1 119.7(3) . 2_657 ?
C9 C1 C1 121.3(2) . 2_657 ?
O2 C2 C1 117.5(2) . . ?
O2 C2 C3 121.2(2) . . ?
C1 C2 C3 121.3(2) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 C10 120.7(3) . . ?
C6 C5 C10 119.5(3) . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 Br6 120.5(2) . . ?
C7 C6 Br6 117.47(19) . . ?
C8 C7 C6 119.1(2) . . ?
C7 C8 C9 121.7(3) . . ?
C10 C9 C1 119.8(2) . . ?
C10 C9 C8 117.5(2) . . ?
C1 C9 C8 122.7(2) . . ?
C4 C10 C9 118.9(3) . . ?
C4 C10 C5 121.1(3) . . ?
C9 C10 C5 120.0(3) . . ?
C16 C11 C12 119.5(3) . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 C17 119.0(2) . . ?
C13 C12 C17 120.7(3) . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 C19 119.6(3) . . ?
C12 C13 C19 120.2(3) . . ?
C13 C14 C15 118.9(3) . . ?
C14 C15 C16 121.0(3) . . ?
C14 C15 C21 120.2(3) . . ?
C16 C15 C21 118.8(2) . . ?
C11 C16 C15 120.0(3) . . ?
C11 C16 C23 120.2(3) . . ?
C15 C16 C23 119.8(2) . . ?
N18 C17 C12 178.2(3) . . ?
N20 C19 C13 178.1(3) . . ?
N22 C21 C15 176.5(3) . . ?
N24 C23 C16 178.5(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.379(3) . ?
C1 C9 1.421(4) . ?
C1 C1 1.483(5) 2_657 ?
C2 O2 1.359(3) . ?
C2 C3 1.408(4) . ?
C3 C4 1.367(4) . ?
C4 C10 1.417(4) . ?
C5 C6 1.354(4) . ?
C5 C10 1.422(4) . ?
C6 C7 1.404(4) . ?
C6 Br6 1.904(3) . ?
C7 C8 1.369(4) . ?
C8 C9 1.423(4) . ?
C9 C10 1.419(4) . ?
C11 C16 1.386(4) . ?
C11 C12 1.386(4) . ?
C12 C13 1.409(4) . ?
C12 C17 1.454(4) . ?
C13 C14 1.385(4) . ?
C13 C19 1.447(4) . ?
C14 C15 1.391(4) . ?
C15 C16 1.398(4) . ?
C15 C21 1.442(4) . ?
C16 C23 1.449(4) . ?
C17 N18 1.134(4) . ?
C19 N20 1.142(4) . ?
C21 N22 1.139(3) . ?
C23 N24 1.138(3) . ?
