#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/22/8102218.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_8102218
loop_
_publ_author_name
'Yan, Xi-Yuan'
'Zhao, Yun'
'Chen, Mu-Wang'
_publ_section_title
;
Crystal structure of 1-(2,6-dichloro-4-trifluoromethylphenyl)-5-((naphthalen-1-
ylmethylene)-amino)-1H-pyrazole-3-carbonitrile, C₂₂H₁₁Cl₂F₃N₄
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              421
_journal_page_last               422
_journal_volume                  222
_journal_year                    2007
_chemical_formula_moiety         'C22 H11 Cl2 F3 N4'
_chemical_formula_sum            'C22 H11 Cl2 F3 N4'
_chemical_formula_weight         459.25
_chemical_name_systematic
; 
1-(2,6-dichloro-4-trifluoromethyl-phenyl)-5-((naphthalen-1-ylmethylene)-
amino)-1H-pyrazole-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 111.643(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.433(3)
_cell_length_b                   22.150(8)
_cell_length_c                   10.728(4)
_cell_measurement_reflns_used    2127
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      2.24
_cell_volume                     2083.5(13)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL(Bruker, 2002)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       phi/omega
_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  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0389
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10791
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.84
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.9620
_exptl_absorpt_correction_T_min  0.8949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3681
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1283
_refine_ls_R_factor_gt           0.1122
_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)+(0.2725P)²+3.8307P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3670
_refine_ls_wR_factor_ref         0.3854
_reflns_number_gt                3128
_reflns_number_total             3681
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            1267-2151.cff
_cod_data_source_block           xg6m
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' 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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_cell_volume        2083.6(12)
_cod_original_sg_symbol_H-M      P12(1)/c1
_cod_database_code               8102218
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.4192(2) 0.42425(8) -0.0293(2) 0.0777(8) Uani 1 4 e d . . .
Cl2 Cl 0.8430(2) 0.26406(11) 0.2513(3) 0.1031(10) Uani 1 4 e d . . .
F1 F 0.3108(8) 0.1884(3) 0.2388(9) 0.140(3) Uani 1 4 e d . . .
F2 F 0.2807(12) 0.2631(3) 0.3295(10) 0.176(4) Uani 1 4 e d . . .
F3 F 0.1521(8) 0.2506(6) 0.1344(11) 0.230(6) Uani 1 4 e d . . .
N1 N 0.7300(5) 0.3716(2) 0.0804(5) 0.0425(12) Uani 1 4 e d . . .
N2 N 0.7695(6) 0.3544(2) -0.0231(5) 0.0455(12) Uani 1 4 e d . . .
N3 N 1.0166(8) 0.3891(3) -0.1832(7) 0.0764(19) Uani 1 4 e d . . .
N4 N 0.7733(6) 0.4398(2) 0.2561(5) 0.0502(13) Uani 1 4 e d . . .
C1 C 0.2846(11) 0.2451(4) 0.2175(10) 0.078(2) Uani 1 4 e d . . .
C2 C 0.4013(7) 0.2783(3) 0.1800(6) 0.0510(16) Uani 1 4 e d . . .
C3 C 0.5488(8) 0.2582(3) 0.2277(7) 0.0574(17) Uani 1 4 e d . . .
H3 H 0.5763 0.2244 0.2829 0.069 Uiso 1 4 e calc R . .
C4 C 0.6558(7) 0.2886(3) 0.1932(7) 0.0535(16) Uani 1 4 e d . . .
C5 C 0.6175(7) 0.3394(2) 0.1119(5) 0.0407(13) Uani 1 4 e d . . .
C6 C 0.4686(7) 0.3592(3) 0.0673(6) 0.0457(14) Uani 1 4 e d . . .
C7 C 0.3598(7) 0.3288(3) 0.0991(6) 0.0513(15) Uani 1 4 e d . . .
H7 H 0.2592 0.3421 0.0666 0.062 Uiso 1 4 e calc R . .
C8 C 0.8765(7) 0.3945(3) -0.0189(5) 0.0432(13) Uani 1 4 e d . . .
C9 C 0.9053(7) 0.4367(3) 0.0853(6) 0.0497(15) Uani 1 4 e d . . .
H9 H 0.9754 0.4682 0.1070 0.060 Uiso 1 4 e calc R . .
C10 C 0.8080(7) 0.4214(2) 0.1473(6) 0.0443(14) Uani 1 4 e d . . .
C11 C 0.9518(7) 0.3908(3) -0.1127(6) 0.0515(15) Uani 1 4 e d . . .
C12 C 0.8290(6) 0.4885(2) 0.3156(6) 0.0430(13) Uani 1 4 e d . . .
H12 H 0.8913 0.5107 0.2827 0.052 Uiso 1 4 e calc R . .
C13 C 0.8026(7) 0.5123(3) 0.4316(6) 0.0467(14) Uani 1 4 e d . . .
C14 C 0.7326(7) 0.4797(3) 0.5100(6) 0.0498(15) Uani 1 4 e d . . .
C15 C 0.6874(9) 0.4183(3) 0.4888(7) 0.0595(17) Uani 1 4 e d . . .
H15 H 0.7055 0.3965 0.4221 0.071 Uiso 1 4 e calc R . .
C16 C 0.6176(10) 0.3906(4) 0.5649(8) 0.077(2) Uani 1 4 e d . . .
H16 H 0.5884 0.3504 0.5491 0.093 Uiso 1 4 e calc R . .
C17 C 0.5898(10) 0.4221(5) 0.6657(8) 0.086(3) Uani 1 4 e d . . .
H17 H 0.5409 0.4031 0.7160 0.103 Uiso 1 4 e calc R . .
C18 C 0.6339(9) 0.4802(5) 0.6905(7) 0.078(3) Uani 1 4 e d . . .
H18 H 0.6155 0.5007 0.7587 0.094 Uiso 1 4 e calc R . .
C19 C 0.7072(8) 0.5107(4) 0.6153(6) 0.0606(18) Uani 1 4 e d . . .
C20 C 0.7533(10) 0.5716(4) 0.6407(7) 0.075(2) Uani 1 4 e d . . .
H20 H 0.7342 0.5921 0.7086 0.091 Uiso 1 4 e calc R . .
C21 C 0.8242(9) 0.6011(4) 0.5697(8) 0.072(2) Uani 1 4 e d . . .
H21 H 0.8562 0.6408 0.5907 0.086 Uiso 1 4 e calc R . .
C22 C 0.8491(8) 0.5715(3) 0.4649(7) 0.0584(17) Uani 1 4 e d . . .
H22 H 0.8978 0.5919 0.4162 0.070 Uiso 1 4 e calc R . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N2 N1 C10 113.6(4) . . ?
N2 N1 C5 120.8(4) . . ?
C10 N1 C5 125.6(5) . . ?
C8 N2 N1 102.7(4) . . ?
C12 N4 C10 119.5(5) . . ?
F3 C1 F2 105.9(9) . . ?
F3 C1 F1 107.3(9) . . ?
F2 C1 F1 102.0(9) . . ?
F3 C1 C2 113.8(8) . . ?
F2 C1 C2 112.3(8) . . ?
F1 C1 C2 114.5(7) . . ?
C3 C2 C7 120.8(6) . . ?
C3 C2 C1 119.2(7) . . ?
C7 C2 C1 120.0(6) . . ?
C2 C3 C4 119.1(6) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 Cl2 120.2(5) . . ?
C5 C4 Cl2 118.5(5) . . ?
C6 C5 C4 118.2(5) . . ?
C6 C5 N1 121.0(5) . . ?
C4 C5 N1 120.8(5) . . ?
C7 C6 C5 121.2(5) . . ?
C7 C6 Cl1 119.7(5) . . ?
C5 C6 Cl1 119.1(4) . . ?
C6 C7 C2 119.3(6) . . ?
C6 C7 H7 120.4 . . ?
C2 C7 H7 120.4 . . ?
N2 C8 C9 113.1(5) . . ?
N2 C8 C11 120.2(5) . . ?
C9 C8 C11 126.6(5) . . ?
C10 C9 C8 104.8(5) . . ?
C10 C9 H9 127.6 . . ?
C8 C9 H9 127.6 . . ?
C9 C10 N1 105.8(5) . . ?
C9 C10 N4 138.7(6) . . ?
N1 C10 N4 115.5(5) . . ?
N3 C11 C8 177.1(7) . . ?
N4 C12 C13 124.7(5) . . ?
N4 C12 H12 117.6 . . ?
C13 C12 H12 117.6 . . ?
C22 C13 C14 119.6(6) . . ?
C22 C13 C12 115.1(6) . . ?
C14 C13 C12 125.3(5) . . ?
C19 C14 C15 117.6(6) . . ?
C19 C14 C13 118.2(6) . . ?
C15 C14 C13 124.2(6) . . ?
C16 C15 C14 121.1(7) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.6(9) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.0(8) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 121.6(8) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 121.8(7) . . ?
C20 C19 C14 119.1(7) . . ?
C18 C19 C14 119.1(8) . . ?
C21 C20 C19 122.2(7) . . ?
C21 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
C20 C21 C22 119.5(7) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C13 C22 C21 121.4(7) . . ?
C13 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
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
Cl1 C6 1.736(6) . ?
Cl2 C4 1.729(7) . ?
F1 C1 1.284(10) . ?
F2 C1 1.279(11) . ?
F3 C1 1.245(12) . ?
N1 N2 1.350(6) . ?
N1 C10 1.372(7) . ?
N1 C5 1.419(7) . ?
N2 C8 1.332(7) . ?
N3 C11 1.134(8) . ?
N4 C12 1.265(7) . ?
N4 C10 1.384(8) . ?
C1 C2 1.497(9) . ?
C2 C3 1.367(10) . ?
C2 C7 1.381(9) . ?
C3 C4 1.374(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(8) . ?
C5 C6 1.377(9) . ?
C6 C7 1.372(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.405(8) . ?
C8 C11 1.433(9) . ?
C9 C10 1.361(8) . ?
C9 H9 0.9300 . ?
C12 C13 1.455(8) . ?
C12 H12 0.9300 . ?
C13 C22 1.387(9) . ?
C13 C14 1.440(9) . ?
C14 C19 1.416(9) . ?
C14 C15 1.418(9) . ?
C15 C16 1.369(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.349(13) . ?
C17 H17 0.9300 . ?
C18 C19 1.413(12) . ?
C18 H18 0.9300 . ?
C19 C20 1.413(11) . ?
C20 C21 1.353(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.394(10) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 N2 C8 0.7(6) . . . . ?
C5 N1 N2 C8 -179.4(5) . . . . ?
F3 C1 C2 C3 -153.8(10) . . . . ?
F2 C1 C2 C3 85.9(10) . . . . ?
F1 C1 C2 C3 -29.8(12) . . . . ?
F3 C1 C2 C7 26.8(12) . . . . ?
F2 C1 C2 C7 -93.5(10) . . . . ?
F1 C1 C2 C7 150.8(8) . . . . ?
C7 C2 C3 C4 -0.6(10) . . . . ?
C1 C2 C3 C4 180.0(7) . . . . ?
C2 C3 C4 C5 0.5(11) . . . . ?
C2 C3 C4 Cl2 -179.7(5) . . . . ?
C3 C4 C5 C6 0.6(9) . . . . ?
Cl2 C4 C5 C6 -179.2(5) . . . . ?
C3 C4 C5 N1 178.0(6) . . . . ?
Cl2 C4 C5 N1 -1.9(8) . . . . ?
N2 N1 C5 C6 -97.5(6) . . . . ?
C10 N1 C5 C6 82.4(7) . . . . ?
N2 N1 C5 C4 85.2(7) . . . . ?
C10 N1 C5 C4 -94.9(7) . . . . ?
C4 C5 C6 C7 -1.7(9) . . . . ?
N1 C5 C6 C7 -179.0(5) . . . . ?
C4 C5 C6 Cl1 177.6(5) . . . . ?
N1 C5 C6 Cl1 0.3(7) . . . . ?
C5 C6 C7 C2 1.5(9) . . . . ?
Cl1 C6 C7 C2 -177.7(5) . . . . ?
C3 C2 C7 C6 -0.4(9) . . . . ?
C1 C2 C7 C6 179.0(6) . . . . ?
N1 N2 C8 C9 0.0(7) . . . . ?
N1 N2 C8 C11 178.5(5) . . . . ?
N2 C8 C9 C10 -0.6(7) . . . . ?
C11 C8 C9 C10 -179.0(6) . . . . ?
C8 C9 C10 N1 0.9(7) . . . . ?
C8 C9 C10 N4 177.6(7) . . . . ?
N2 N1 C10 C9 -1.1(7) . . . . ?
C5 N1 C10 C9 179.0(5) . . . . ?
N2 N1 C10 N4 -178.6(5) . . . . ?
C5 N1 C10 N4 1.5(8) . . . . ?
C12 N4 C10 C9 10.2(12) . . . . ?
C12 N4 C10 N1 -173.3(5) . . . . ?
N2 C8 C11 N3 -155(16) . . . . ?
C9 C8 C11 N3 24(16) . . . . ?
C10 N4 C12 C13 -179.3(5) . . . . ?
N4 C12 C13 C22 -167.8(6) . . . . ?
N4 C12 C13 C14 11.4(9) . . . . ?
C22 C13 C14 C19 2.9(9) . . . . ?
C12 C13 C14 C19 -176.3(5) . . . . ?
C22 C13 C14 C15 -177.0(6) . . . . ?
C12 C13 C14 C15 3.8(10) . . . . ?
C19 C14 C15 C16 1.9(10) . . . . ?
C13 C14 C15 C16 -178.2(7) . . . . ?
C14 C15 C16 C17 -0.3(12) . . . . ?
C15 C16 C17 C18 -1.0(13) . . . . ?
C16 C17 C18 C19 0.6(12) . . . . ?
C17 C18 C19 C20 179.9(7) . . . . ?
C17 C18 C19 C14 1.1(11) . . . . ?
C15 C14 C19 C20 178.9(6) . . . . ?
C13 C14 C19 C20 -1.0(9) . . . . ?
C15 C14 C19 C18 -2.3(9) . . . . ?
C13 C14 C19 C18 177.9(6) . . . . ?
C18 C19 C20 C21 179.7(7) . . . . ?
C14 C19 C20 C21 -1.5(11) . . . . ?
C19 C20 C21 C22 2.1(12) . . . . ?
C14 C13 C22 C21 -2.4(10) . . . . ?
C12 C13 C22 C21 176.9(6) . . . . ?
C20 C21 C22 C13 -0.1(11) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653927
