#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/68/2206812.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_2206812
loop_
_publ_author_name
'Zhong, Ping'
'Yang, Zhiping'
'Shi, Qian'
'Hu, Maolin'
'Li, Shuyan'
'Tang, Riyuan'
_publ_section_title
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-1H-pyrazole-3-carbonitrile
_journal_coeditor_code           WW6369
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2972
_journal_page_last               o2973
_journal_paper_doi               10.1107/S1600536805025699
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C16 H7 Cl2 F3 N4 O'
_chemical_formula_moiety         'C16 H7 Cl2 F3 N4 O'
_chemical_formula_sum            'C16 H7 Cl2 F3 N4 O'
_chemical_formula_weight         399.16
_chemical_melting_point          450.0(10)
_chemical_name_systematic
;
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-[(2-furyl)methyleneamino]-
1H-pyrazole-3-carbonitrile
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 92.0840(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8828(9)
_cell_length_b                   6.7072(5)
_cell_length_c                   21.1191(16)
_cell_measurement_reflns_used    3298
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.02
_cell_measurement_theta_min      3.18
_cell_volume                     1682.1(2)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'XP (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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8571
_diffrn_reflns_theta_full        25.19
_diffrn_reflns_theta_max         25.19
_diffrn_reflns_theta_min         1.93
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.430
_exptl_absorpt_correction_T_max  0.8854
_exptl_absorpt_correction_T_min  0.8535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.29
_refine_diff_density_max         1.122
_refine_diff_density_min         -0.644
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0688
_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)+(0.1164P)²+2.0094P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1953
_refine_ls_wR_factor_ref         0.2039
_reflns_number_gt                2571
_reflns_number_total             3013
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ww6369.cif
_cod_data_source_block           I
_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 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2206812
_cod_database_fobs_code          2206812
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_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 0.58604(10) 0.09721(15) 0.17137(5) 0.0678(4) Uani d . 1 Cl
Cl2 0.60827(9) 0.75002(15) 0.02417(5) 0.0637(4) Uani d . 1 Cl
F1 0.2558(5) 0.7800(15) 0.1718(6) 0.293(6) Uani d . 1 F
F2 0.1880(3) 0.6094(13) 0.1130(2) 0.206(3) Uani d . 1 F
F3 0.2255(5) 0.5229(17) 0.2002(4) 0.308(7) Uani d . 1 F
O1 0.8328(2) 0.9534(4) 0.21212(12) 0.0528(6) Uani d . 1 O
N1 0.6953(2) 0.3706(4) 0.08051(14) 0.0438(7) Uani d . 1 N
N2 0.7008(2) 0.2090(4) 0.04282(14) 0.0485(7) Uani d . 1 N
N3 0.8761(4) -0.1086(6) -0.0323(2) 0.0843(13) Uani d . 1 N
N4 0.8054(2) 0.6190(4) 0.13362(14) 0.0450(7) Uani d . 1 N
C1 0.2601(4) 0.5992(10) 0.1540(3) 0.0871(16) Uani d . 1 C
C2 0.3750(3) 0.5423(7) 0.13571(18) 0.0580(10) Uani d . 1 C
C3 0.4202(3) 0.3669(6) 0.15846(19) 0.0561(9) Uani d . 1 C
H3 0.3797 0.2856 0.1851 0.067 Uiso calc R 1 H
C4 0.5269(3) 0.3135(5) 0.14114(17) 0.0466(8) Uani d . 1 C
C5 0.5876(3) 0.4327(5) 0.10036(16) 0.0412(7) Uani d . 1 C
C6 0.5386(3) 0.6063(5) 0.07742(17) 0.0455(8) Uani d . 1 C
C7 0.4320(3) 0.6633(6) 0.09581(19) 0.0560(9) Uani d . 1 C
H7 0.3999 0.7819 0.0811 0.067 Uiso calc R 1 H
C8 0.8478(3) 0.0251(6) -0.0030(2) 0.0597(10) Uani d . 1 C
C9 0.8111(3) 0.1898(6) 0.03400(17) 0.0499(8) Uani d . 1 C
C10 0.8752(3) 0.3377(6) 0.06397(18) 0.0513(9) Uani d . 1 C
H10 0.9529 0.3542 0.0636 0.062 Uiso calc R 1 H
C11 0.7988(3) 0.4543(5) 0.09428(16) 0.0430(7) Uani d . 1 C
C12 0.8959(3) 0.7205(5) 0.13453(16) 0.0456(8) Uani d . 1 C
H12 0.9534 0.6794 0.1088 0.055 Uiso calc R 1 H
C13 0.9146(3) 0.8937(5) 0.17273(16) 0.0437(8) Uani d . 1 C
C14 1.0007(3) 1.0250(6) 0.17631(19) 0.0568(10) Uani d . 1 C
H14 1.0670 1.0174 0.1544 0.068 Uiso calc R 1 H
C15 0.9719(3) 1.1751(6) 0.21907(18) 0.0545(9) Uani d . 1 C
H15 1.0145 1.2862 0.2309 0.065 Uiso calc R 1 H
C16 0.8701(3) 1.1248(6) 0.23926(19) 0.0551(9) Uani d . 1 C
H16 0.8302 1.1985 0.2682 0.066 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 C13 106.2(3) yes
N2 N1 C11 113.0(3) yes
N2 N1 C5 118.2(3) ?
C11 N1 C5 128.7(3) ?
C9 N2 N1 103.2(3) yes
C12 N4 C11 117.7(3) ?
F3 C1 F2 111.0(7) yes
F3 C1 F1 98.6(8) ?
F2 C1 F1 97.1(7) ?
F3 C1 C2 116.9(5) ?
F2 C1 C2 117.8(5) ?
F1 C1 C2 111.8(6) ?
C7 C2 C3 121.9(3) ?
C7 C2 C1 119.3(4) ?
C3 C2 C1 118.8(4) ?
C2 C3 C4 118.8(4) ?
C2 C3 H3 120.6 ?
C4 C3 H3 120.6 ?
C3 C4 C5 121.0(3) ?
C3 C4 Cl1 119.1(3) ?
C5 C4 Cl1 119.9(3) ?
C6 C5 C4 118.6(3) ?
C6 C5 N1 121.0(3) ?
C4 C5 N1 120.3(3) ?
C5 C6 C7 120.6(3) ?
C5 C6 Cl2 119.7(3) ?
C7 C6 Cl2 119.6(3) ?
C2 C7 C6 119.0(4) ?
C2 C7 H7 120.5 ?
C6 C7 H7 120.5 ?
N3 C8 C9 179.1(5) yes
N2 C9 C10 113.1(3) yes
N2 C9 C8 118.1(3) ?
C10 C9 C8 128.8(3) ?
C11 C10 C9 104.9(3) yes
C11 C10 H10 127.5 ?
C9 C10 H10 127.5 ?
C10 C11 N1 105.7(3) yes
C10 C11 N4 135.3(3) ?
N1 C11 N4 118.9(3) ?
N4 C12 C13 123.9(3) ?
N4 C12 H12 118.0 ?
C13 C12 H12 118.0 ?
C14 C13 O1 109.3(3) yes
C14 C13 C12 131.6(3) ?
O1 C13 C12 119.0(3) ?
C13 C14 C15 107.6(3) yes
C13 C14 H14 126.2 ?
C15 C14 H14 126.2 ?
C16 C15 C14 105.6(3) yes
C16 C15 H15 127.2 ?
C14 C15 H15 127.2 ?
C15 C16 O1 111.4(3) yes
C15 C16 H16 124.3 ?
O1 C16 H16 124.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C4 1.724(4) yes
Cl2 C6 1.716(4) ?
F1 C1 1.271(9) yes
F2 C1 1.198(7) ?
F3 C1 1.188(7) ?
O1 C16 1.352(4) yes
O1 C13 1.362(4) yes
N1 N2 1.348(4) yes
N1 C11 1.374(4) yes
N1 C5 1.423(4) ?
N2 C9 1.337(5) yes
N3 C8 1.147(5) yes
N4 C12 1.273(4) yes
N4 C11 1.382(4) yes
C1 C2 1.483(6) ?
C2 C7 1.367(6) ?
C2 C3 1.373(6) ?
C3 C4 1.380(5) ?
C3 H3 0.9300 ?
C4 C5 1.395(5) ?
C5 C6 1.382(5) ?
C6 C7 1.393(5) ?
C7 H7 0.9300 ?
C8 C9 1.430(5) ?
C9 C10 1.389(5) yes
C10 C11 1.374(5) yes
C10 H10 0.9300 ?
C12 C13 1.427(5) ?
C12 H12 0.9300 ?
C13 C14 1.350(5) yes
C14 C15 1.403(5) yes
C14 H14 0.9300 ?
C15 C16 1.340(6) yes
C15 H15 0.9300 ?
C16 H16 0.9300 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30654851
2 PubChem 139068339
