#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204083.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_2204083
loop_
_publ_author_name
'Yang, Zhiping'
'Zhong, Ping'
'Hu, Maolin'
_publ_section_title
;
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(2,5-dioxo-2,5-dihydro-1H-
pyrrol-1-yl)-1H-pyrazole-3-carbonitrile
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1350
_journal_page_last               o1351
_journal_paper_doi               10.1107/S1600536804016678
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C15 H5 Cl2 F3 N4 O2'
_chemical_formula_moiety         'C15 H5 Cl2 F3 N4 O2'
_chemical_formula_sum            'C15 H5 Cl2 F3 N4 O2'
_chemical_formula_weight         401.13
_chemical_name_systematic
;
1-[2,6-Dichloro-4-(trifluoromethyl)phenyl]-5-(2,5-dioxo-2,5-dihydro-1H-
pyrrol-1-yl)-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                 104.2170(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8261(10)
_cell_length_b                   8.9942(7)
_cell_length_c                   14.6896(12)
_cell_measurement_reflns_used    3254
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      2.42
_cell_volume                     1642.7(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9003
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0'?
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_T_max  0.9162
_exptl_absorpt_correction_T_min  0.8315
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.717
_refine_diff_density_min         -0.381
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3225
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0552
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0945P)²+0.8386P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1650
_reflns_number_gt                2660
_reflns_number_total             3225
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6121.cif
_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 'Integration' changed
to 'integration' 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 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204083
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 0.07471(6) 0.47385(9) 0.19496(6) 0.0638(3) Uani d . 1 Cl
Cl2 0.01644(7) 0.75112(11) 0.50326(5) 0.0729(3) Uani d . 1 Cl
O1 0.2530(2) 1.0201(2) 0.49559(16) 0.0758(7) Uani d . 1 O
O2 0.1035(2) 0.8294(3) 0.20621(15) 0.0750(7) Uani d . 1 O
N1 0.14676(16) 0.6217(2) 0.38311(15) 0.0424(5) Uani d . 1 N
N3 0.4332(2) 0.3464(3) 0.5455(2) 0.0739(8) Uani d . 1 N
N4 0.17897(17) 0.8822(2) 0.36239(15) 0.0420(5) Uani d . 1 N
N2 0.19715(18) 0.4966(2) 0.42196(17) 0.0470(5) Uani d . 1 N
C2 -0.1867(2) 0.5922(3) 0.2753(2) 0.0497(6) Uani d . 1 C
C3 -0.1456(2) 0.6599(3) 0.3616(2) 0.0512(7) Uani d . 1 C
H3 -0.1915 0.6974 0.3962 0.061 Uiso calc R 1 H
C4 -0.0359(2) 0.6708(3) 0.39517(18) 0.0459(6) Uani d . 1 C
C5 0.0337(2) 0.6150(3) 0.34441(18) 0.0407(6) Uani d . 1 C
C6 -0.0096(2) 0.5478(3) 0.25839(19) 0.0439(6) Uani d . 1 C
C7 -0.1193(2) 0.5367(3) 0.2231(2) 0.0487(6) Uani d . 1 C
H7 -0.1476 0.4925 0.1650 0.058 Uiso calc R 1 H
C8 0.2144(2) 0.7403(3) 0.39565(18) 0.0411(5) Uani d . 1 C
C9 0.3126(2) 0.6927(3) 0.44547(18) 0.0468(6) Uani d . 1 C
H9 0.3754 0.7479 0.4656 0.056 Uiso calc R 1 H
C10 0.2971(2) 0.5416(3) 0.45920(19) 0.0461(6) Uani d . 1 C
C11 0.3738(2) 0.4324(3) 0.5067(2) 0.0538(7) Uani d . 1 C
C12 0.1275(2) 0.9176(3) 0.26865(19) 0.0475(6) Uani d . 1 C
C13 0.2040(2) 1.0135(3) 0.4153(2) 0.0475(6) Uani d . 1 C
C14 0.1575(2) 1.1359(3) 0.3503(2) 0.0539(7) Uani d . 1 C
H14 0.1594 1.2362 0.3661 0.065 Uiso calc R 1 H
C15 0.1129(2) 1.0806(3) 0.2666(2) 0.0520(7) Uani d . 1 C
H15 0.0778 1.1356 0.2145 0.062 Uiso calc R 1 H
F1 -0.33778(17) 0.5257(3) 0.15503(17) 0.1062(9) Uani d . 1 F
F2 -0.34456(19) 0.4721(3) 0.2896(2) 0.1064(9) Uani d . 1 F
F3 -0.35836(17) 0.6960(3) 0.2506(3) 0.1303(13) Uani d . 1 F
C1 -0.3058(3) 0.5759(4) 0.2407(2) 0.0676(9) Uani d . 1 C
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
N2 N1 C8 111.9(2) yes
N2 N1 C5 117.93(19) yes
C8 N1 C5 129.9(2) yes
C8 N4 C13 124.2(2) yes
C8 N4 C12 125.5(2) yes
C13 N4 C12 109.8(2) yes
C10 N2 N1 103.5(2) yes
C7 C2 C3 121.1(3) no
C7 C2 C1 120.2(3) no
C3 C2 C1 118.7(3) no
C4 C3 C2 118.9(3) no
C4 C3 H3 120.5 no
C2 C3 H3 120.5 no
C3 C4 C5 121.2(2) no
C3 C4 Cl2 119.5(2) no
C5 C4 Cl2 119.3(2) no
C6 C5 C4 118.6(2) no
C6 C5 N1 121.5(2) no
C4 C5 N1 119.8(2) no
C7 C6 C5 121.2(2) no
C7 C6 Cl1 119.1(2) no
C5 C6 Cl1 119.7(2) no
C6 C7 C2 119.0(2) no
C6 C7 H7 120.5 no
C2 C7 H7 120.5 no
N1 C8 C9 107.6(2) yes
N1 C8 N4 121.8(2) yes
C9 C8 N4 130.7(2) yes
C8 C9 C10 103.8(2) yes
C8 C9 H9 128.1 no
C10 C9 H9 128.1 no
N2 C10 C9 113.3(2) yes
N2 C10 C11 117.8(2) yes
C9 C10 C11 128.9(3) yes
N3 C11 C10 178.7(3) yes
O2 C12 N4 124.8(3) no
O2 C12 C15 129.5(3) no
N4 C12 C15 105.7(2) yes
O1 C13 N4 125.5(3) no
O1 C13 C14 129.0(3) yes
N4 C13 C14 105.5(2) yes
C15 C14 C13 109.5(3) yes
C15 C14 H14 125.3 no
C13 C14 H14 125.3 no
C14 C15 C12 109.4(2) no
C14 C15 H15 125.3 no
C12 C15 H15 125.3 no
F3 C1 F1 110.3(3) no
F3 C1 F2 104.3(3) no
F1 C1 F2 101.8(3) no
F3 C1 C2 113.3(3) no
F1 C1 C2 114.5(3) no
F2 C1 C2 111.6(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C6 1.725(3) no
Cl2 C4 1.724(3) no
O1 C13 1.194(4) no
O2 C12 1.194(3) no
N1 N2 1.352(3) yes
N1 C8 1.359(3) yes
N1 C5 1.423(3) yes
N3 C11 1.136(4) yes
N4 C8 1.401(3) yes
N4 C13 1.407(3) yes
N4 C12 1.410(3) yes
N2 C10 1.327(3) yes
C2 C7 1.381(4) no
C2 C3 1.389(4) no
C2 C1 1.495(4) no
C3 C4 1.375(4) no
C3 H3 0.9300 no
C4 C5 1.390(4) no
C5 C6 1.388(4) no
C6 C7 1.379(4) no
C7 H7 0.9300 no
C8 C9 1.361(4) yes
C9 C10 1.395(4) yes
C9 H9 0.9300 ?
C10 C11 1.443(4) yes
C12 C15 1.477(4) yes
C13 C14 1.483(4) no
C14 C15 1.319(4) yes
C14 H14 0.9300 no
C15 H15 0.9300 no
F1 C1 1.305(4) no
F2 C1 1.345(4) no
F3 C1 1.300(4) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C7 H7 O1 4_575 0.93 2.50 3.380(4) 157 yes
C14 H14 N2 1_565 0.93 2.49 3.410(3) 170 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130575
