#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/55/2205578.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2205578
loop_
_publ_author_name
'Zhang, Xiaohong'
'Yang, Zhiping'
'Zhong, Ping'
'Hu, Maolin'
_publ_section_title
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(4-methoxyphenyl)methyleneimino]-1H-pyrazole-3-carbonitrile
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o908
_journal_page_last               o909
_journal_paper_doi               10.1107/S1600536805006707
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C19 H11 Cl2 F3 N4 O'
_chemical_formula_moiety         'C19 H11 Cl2 F3 N4 O'
_chemical_formula_sum            'C19 H11 Cl2 F3 N4 O'
_chemical_formula_weight         439.22
_chemical_melting_point          .408E-305
_chemical_name_systematic
;1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-5-[(4-methoxyphenyl)methylene]imino-
1H-pyrazole-3-enitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                77.464(3)
_cell_angle_beta                 83.116(3)
_cell_angle_gamma                81.470(3)
_cell_formula_units_Z            2
_cell_length_a                   6.7145(12)
_cell_length_b                   10.931(2)
_cell_length_c                   13.616(3)
_cell_measurement_reflns_used    1222
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.92
_cell_measurement_theta_min      3.07
_cell_volume                     960.8(3)
_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  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0695
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4901
_diffrn_reflns_theta_full        25.28
_diffrn_reflns_theta_max         25.28
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.146
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.146
_refine_ls_R_factor_all          0.125
_refine_ls_R_factor_gt           0.090
_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)+(0.081P)²+0.8129P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.194
_refine_ls_wR_factor_ref         0.211
_reflns_number_gt                2393
_reflns_number_total             3401
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            rz6054.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     -P1
_cod_database_code               2205578
_cod_database_fobs_code          2205578
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cl1 0.1725(2) 0.69202(16) 0.18613(11) 0.0764(5) Uani d . 1 Cl
Cl2 0.7008(2) 1.03071(14) 0.12882(11) 0.0651(5) Uani d . 1 Cl
F1 0.9684(7) 0.7064(5) -0.1000(4) 0.1314(19) Uani d . 1 F
F2 0.7021(9) 0.7183(7) -0.1621(3) 0.170(3) Uani d . 1 F
F3 0.7977(9) 0.5585(4) -0.0547(4) 0.145(2) Uani d . 1 F
O1 1.3072(6) 0.5472(4) 0.6076(3) 0.0686(11) Uani d . 1 O
N1 0.3408(6) 0.9099(4) 0.2325(3) 0.0446(10) Uani d . 1 N
N2 0.1621(6) 0.9797(4) 0.2154(3) 0.0510(11) Uani d . 1 N
N3 -0.2413(8) 1.1477(5) 0.3329(4) 0.0792(16) Uani d . 1 N
N4 0.5745(6) 0.8291(4) 0.3556(3) 0.0463(10) Uani d . 1 N
C1 0.7839(12) 0.6794(7) -0.0775(5) 0.084(2) Uani d . 1 C
C2 0.6707(8) 0.7397(5) 0.0048(4) 0.0548(14) Uani d . 1 C
C3 0.4970(8) 0.6948(5) 0.0524(3) 0.0547(13) Uani d . 1 C
H3 0.4517 0.6267 0.0348 0.066 Uiso calc R 1 H
C4 0.3905(8) 0.7518(5) 0.1264(3) 0.0482(12) Uani d . 1 C
C5 0.4524(7) 0.8522(5) 0.1536(3) 0.0422(11) Uani d . 1 C
C6 0.6244(7) 0.8996(5) 0.1023(3) 0.0449(12) Uani d . 1 C
C7 0.7358(7) 0.8425(5) 0.0273(3) 0.0505(13) Uani d . 1 C
H7 0.8521 0.8737 -0.0067 0.061 Uiso calc R 1 H
C8 0.3947(7) 0.8980(4) 0.3285(3) 0.0423(11) Uani d . 1 C
C9 0.2391(7) 0.9673(5) 0.3748(3) 0.0485(12) Uani d . 1 C
H9 0.2279 0.9801 0.4406 0.058 Uiso calc R 1 H
C10 0.1016(7) 1.0144(5) 0.3033(3) 0.0458(12) Uani d . 1 C
C11 -0.0889(9) 1.0893(5) 0.3178(4) 0.0547(14) Uani d . 1 C
C12 0.5927(7) 0.7931(5) 0.4503(3) 0.0461(12) Uani d . 1 C
H12 0.4813 0.8104 0.4950 0.055 Uiso calc R 1 H
C13 0.7754(7) 0.7277(4) 0.4915(3) 0.0432(11) Uani d . 1 C
C14 0.9544(7) 0.7050(5) 0.4310(3) 0.0467(12) Uani d . 1 C
H14 0.9561 0.7320 0.3613 0.056 Uiso calc R 1 H
C15 1.1246(8) 0.6447(5) 0.4715(4) 0.0521(13) Uani d . 1 C
H15 1.2419 0.6303 0.4296 0.063 Uiso calc R 1 H
C16 1.1264(7) 0.6034(5) 0.5761(4) 0.0463(12) Uani d . 1 C
C17 0.9533(8) 0.6251(5) 0.6368(3) 0.0520(13) Uani d . 1 C
H17 0.9528 0.5985 0.7065 0.062 Uiso calc R 1 H
C18 0.7804(8) 0.6859(5) 0.5954(3) 0.0495(13) Uani d . 1 C
H18 0.6634 0.6997 0.6376 0.059 Uiso calc R 1 H
C19 1.3214(11) 0.5024(7) 0.7126(5) 0.091(2) Uani d . 1 C
H19A 1.2795 0.5708 0.7474 0.137 Uiso calc R 1 H
H19B 1.4588 0.4686 0.7244 0.137 Uiso calc R 1 H
H19C 1.2355 0.4374 0.7373 0.137 Uiso calc R 1 H
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'
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_publ_flag
C16 O1 C19 118.3(5) ?
N2 N1 C8 114.1(4) yes
N2 N1 C5 119.3(3) ?
C8 N1 C5 126.6(4) ?
N1 N2 C10 103.0(4) yes
C8 N4 C12 116.6(4) yes
F3 C1 F2 108.6(7) ?
F3 C1 F1 105.9(6) ?
F2 C1 F1 103.7(6) ?
F3 C1 C2 112.3(6) ?
F2 C1 C2 112.0(6) ?
F1 C1 C2 113.7(6) ?
C3 C2 C7 121.3(4) ?
C3 C2 C1 118.9(6) ?
C7 C2 C1 119.8(5) ?
C2 C3 C4 118.9(5) ?
C2 C3 H3 120.5 ?
C4 C3 H3 120.5 ?
C5 C4 C3 121.9(5) ?
C5 C4 Cl1 120.1(4) ?
C3 C4 Cl1 117.9(4) ?
C4 C5 C6 118.5(4) ?
C4 C5 N1 121.4(4) ?
C6 C5 N1 120.1(4) ?
C5 C6 C7 120.5(5) ?
C5 C6 Cl2 120.3(4) ?
C7 C6 Cl2 119.2(4) ?
C2 C7 C6 118.8(5) ?
C2 C7 H7 120.6 ?
C6 C7 H7 120.6 ?
C9 C8 N4 135.8(4) ?
C9 C8 N1 104.4(4) ?
N4 C8 N1 119.8(4) ?
C8 C9 C10 105.9(4) ?
C8 C9 H9 127.1 ?
C10 C9 H9 127.1 ?
N2 C10 C9 112.6(4) ?
N2 C10 C11 121.0(4) ?
C9 C10 C11 126.4(4) ?
N3 C11 C10 177.7(6) ?
N4 C12 C13 123.8(4) ?
N4 C12 H12 118.1 ?
C13 C12 H12 118.1 ?
C18 C13 C14 117.2(4) ?
C18 C13 C12 120.4(4) ?
C14 C13 C12 122.4(4) ?
C15 C14 C13 121.3(4) ?
C15 C14 H14 119.3 ?
C13 C14 H14 119.3 ?
C14 C15 C16 120.5(4) ?
C14 C15 H15 119.7 ?
C16 C15 H15 119.7 ?
O1 C16 C17 126.0(5) ?
O1 C16 C15 114.9(4) ?
C17 C16 C15 119.1(5) ?
C16 C17 C18 120.2(4) ?
C16 C17 H17 119.9 ?
C18 C17 H17 119.9 ?
C17 C18 C13 121.6(5) ?
C17 C18 H18 119.2 ?
C13 C18 H18 119.2 ?
O1 C19 H19A 109.5 ?
O1 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
O1 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.732(5) ?
Cl2 C6 1.713(5) ?
F1 C1 1.302(8) ?
F2 C1 1.296(8) ?
F3 C1 1.282(8) ?
O1 C16 1.350(6) ?
O1 C19 1.418(7) ?
N1 N2 1.340(5) yes
N1 C8 1.371(5) yes
N1 C5 1.441(5) ?
N2 C10 1.333(6) yes
N3 C11 1.144(7) ?
N4 C8 1.370(6) yes
N4 C12 1.278(5) yes
C1 C2 1.495(8) ?
C2 C3 1.368(7) ?
C2 C7 1.370(7) ?
C3 C4 1.373(6) ?
C3 H3 0.9300 ?
C4 C5 1.364(7) ?
C5 C6 1.385(7) ?
C6 C7 1.394(6) ?
C7 H7 0.9300 ?
C8 C9 1.370(6) ?
C9 C10 1.386(7) ?
C9 H9 0.9300 ?
C10 C11 1.430(7) ?
C12 C13 1.436(7) ?
C12 H12 0.9300 ?
C13 C18 1.391(6) ?
C13 C14 1.395(6) ?
C14 C15 1.348(7) ?
C14 H14 0.9300 ?
C15 C16 1.399(7) ?
C15 H15 0.9300 ?
C16 C17 1.365(7) ?
C17 C18 1.368(7) ?
C17 H17 0.9300 ?
C18 H18 0.9300 ?
C19 H19A 0.9600 ?
C19 H19B 0.9600 ?
C19 H19C 0.9600 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654801
