#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/58/2205841.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_2205841
loop_
_publ_author_name
'Chen, Di-Mei'
'Zhong, Ping'
'Yang, Zhi-Ping'
'Hu, Mao-Lin'
_publ_section_title
;N,N'-Bis{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-5-yl}-1,4-benzenediamide
 dimethylformamide disolvate
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1362
_journal_page_last               o1363
_journal_paper_doi               10.1107/S1600536805011153
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C30 H12 Cl4 F6 N8 O2 , 2C3 H7 N O'
_chemical_formula_moiety         'C30 H12 Cl4 F6 N8 O2 , 2C3 H7 N O'
_chemical_formula_sum            'C36 H26 Cl4 F6 N10 O4'
_chemical_formula_weight         918.47
_chemical_melting_point          525
_chemical_name_systematic
;
N,N'-bis{3-cyano-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-1H-pyrazol-5-
yl}-1,4-benzenediamide bis(dimethylformamide) solvate
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 102.526(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.7657(19)
_cell_length_b                   27.655(6)
_cell_length_c                   9.902(2)
_cell_measurement_reflns_used    1787
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.2
_cell_volume                     2075.9(8)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX CCD 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  0.046
_diffrn_reflns_av_sigmaI/netI    0.064
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10903
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         25.2
_diffrn_reflns_theta_min         2.2
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.36
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             932
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.90
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.18
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.18
_refine_ls_R_factor_all          0.145
_refine_ls_R_factor_gt           0.098
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0905P)²+7.5446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.268
_refine_ls_wR_factor_ref         0.248
_reflns_number_gt                3007
_reflns_number_total             3735
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya6241.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_cell_volume        2075.8(8)
_cod_original_sg_symbol_Hall     -P2ybc
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2205841
_cod_database_fobs_code          2205841
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_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 -0.2111(3) 0.38900(7) 0.7632(2) 0.0642(6) Uani d . 1 Cl
Cl2 0.3780(3) 0.30056(10) 0.6961(3) 0.0889(9) Uani d . 1 Cl
O1 0.5183(7) 0.47507(19) 0.8628(4) 0.0624(15) Uani d . 1 O
O2 0.0365(8) 0.4322(2) 0.4887(5) 0.0757(17) Uani d . 1 O
F1 -0.3452(10) 0.2958(3) 0.2871(7) 0.159(4) Uani d . 1 F
F2 -0.1098(11) 0.2676(3) 0.2582(7) 0.159(3) Uani d . 1 F
F3 -0.2476(11) 0.2291(3) 0.3732(8) 0.152(3) Uani d . 1 F
N1 0.1684(6) 0.36312(17) 0.8413(4) 0.0353(11) Uani d . 1 N
N2 0.1596(7) 0.34197(19) 0.9632(5) 0.0440(13) Uani d . 1 N
N3 0.3111(10) 0.3514(2) 1.3163(6) 0.070(2) Uani d . 1 N
N4 0.2998(7) 0.42810(18) 0.7425(4) 0.0380(12) Uani d . 1 N
H4 0.2349 0.4219 0.6624 0.046 Uiso calc R 1 H
N5 -0.0567(9) 0.4459(2) 0.2585(6) 0.0622(17) Uani d . 1 N
C1 -0.2129(14) 0.2733(4) 0.3524(12) 0.093(3) Uani d . 1 C
C2 -0.1119(10) 0.2977(2) 0.4798(7) 0.0528(18) Uani d . 1 C
C3 -0.1991(9) 0.3287(2) 0.5534(7) 0.0459(16) Uani d . 1 C
H3 -0.3192 0.3347 0.5232 0.055 Uiso calc R 1 H
C4 -0.1048(8) 0.3505(2) 0.6715(6) 0.0393(14) Uani d . 1 C
C5 0.0713(8) 0.3420(2) 0.7170(6) 0.0342(13) Uani d . 1 C
C6 0.1560(8) 0.3114(2) 0.6407(7) 0.0458(16) Uani d . 1 C
C7 0.0631(10) 0.2896(3) 0.5212(7) 0.0563(19) Uani d . 1 C
H7 0.1206 0.2695 0.4698 0.068 Uiso calc R 1 H
C8 0.2624(8) 0.3704(2) 1.0558(6) 0.0392(14) Uani d . 1 C
C9 0.3345(8) 0.4088(2) 0.9975(6) 0.0403(15) Uani d . 1 C
H9 0.4086 0.4330 1.0425 0.048 Uiso calc R 1 H
C10 0.2710(8) 0.4029(2) 0.8575(5) 0.0352(13) Uani d . 1 C
C11 0.2882(10) 0.3589(2) 1.2024(7) 0.0483(16) Uani d . 1 C
C12 0.4285(8) 0.4623(2) 0.7537(5) 0.0380(14) Uani d . 1 C
C13 0.4590(8) 0.4812(2) 0.6181(6) 0.0371(14) Uani d . 1 C
C14 0.4528(8) 0.4520(2) 0.5055(6) 0.0390(14) Uani d . 1 C
H14 0.4220 0.4196 0.5093 0.047 Uiso calc R 1 H
C15 0.5073(9) 0.5293(2) 0.6143(6) 0.0434(16) Uani d . 1 C
H15 0.5131 0.5489 0.6914 0.052 Uiso calc R 1 H
C16 -0.040(3) 0.4767(6) 0.1528(18) 0.209(11) Uani d . 1 C
H16A 0.0268 0.5046 0.1905 0.313 Uiso calc R 1 H
H16B -0.1550 0.4866 0.1034 0.313 Uiso calc R 1 H
H16C 0.0196 0.4603 0.0908 0.313 Uiso calc R 1 H
C17 -0.1547(19) 0.4028(7) 0.2178(18) 0.192(9) Uani d . 1 C
H17A -0.1578 0.3837 0.2983 0.288 Uiso calc R 1 H
H17B -0.0994 0.3846 0.1563 0.288 Uiso calc R 1 H
H17C -0.2728 0.4110 0.1714 0.288 Uiso calc R 1 H
C18 0.0167(16) 0.4501(6) 0.3822(10) 0.127(5) Uani d . 1 C
H18 0.0803 0.4789 0.3924 0.153 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C10 N1 N2 . . 112.9(4)
C10 N1 C5 . . 128.9(5)
N2 N1 C5 . . 118.3(4)
C8 N2 N1 . . 102.7(5)
C12 N4 C10 . . 121.7(5)
C12 N4 H4 . . 119.2
C10 N4 H4 . . 119.2
C18 N5 C16 . . 126.6(14)
C18 N5 C17 . . 117.4(13)
C16 N5 C17 . . 115.8(13)
F1 C1 F3 . . 112.2(10)
F1 C1 F2 . . 104.0(11)
F3 C1 F2 . . 100.0(9)
F1 C1 C2 . . 115.8(8)
F3 C1 C2 . . 112.7(9)
F2 C1 C2 . . 110.6(9)
C7 C2 C3 . . 121.0(6)
C7 C2 C1 . . 119.5(7)
C3 C2 C1 . . 119.6(7)
C4 C3 C2 . . 119.0(6)
C4 C3 H3 . . 120.5
C2 C3 H3 . . 120.5
C5 C4 C3 . . 121.1(6)
C5 C4 Cl1 . . 119.6(5)
C3 C4 Cl1 . . 119.4(5)
C4 C5 C6 . . 119.0(5)
C4 C5 N1 . . 121.3(5)
C6 C5 N1 . . 119.7(5)
C7 C6 C5 . . 120.6(6)
C7 C6 Cl2 . . 119.9(5)
C5 C6 Cl2 . . 119.5(5)
C2 C7 C6 . . 119.5(6)
C2 C7 H7 . . 120.3
C6 C7 H7 . . 120.3
N2 C8 C9 . . 113.7(5)
N2 C8 C11 . . 119.3(5)
C9 C8 C11 . . 127.0(6)
C10 C9 C8 . . 103.8(5)
C10 C9 H9 . . 128.1
C8 C9 H9 . . 128.1
N1 C10 C9 . . 106.9(5)
N1 C10 N4 . . 120.4(5)
C9 C10 N4 . . 132.7(5)
N3 C11 C8 . . 177.8(8)
O1 C12 N4 . . 123.2(5)
O1 C12 C13 . . 121.7(6)
N4 C12 C13 . . 115.0(5)
C14 C13 C15 . . 120.5(5)
C14 C13 C12 . . 122.4(5)
C15 C13 C12 . . 117.0(5)
C13 C14 C15 . 3_666 120.1(5)
C13 C14 H14 . . 120.0
C15 C14 H14 3_666 . 120.0
C13 C15 C14 . 3_666 119.5(5)
C13 C15 H15 . . 120.3
C14 C15 H15 3_666 . 120.3
N5 C16 H16A . . 109.5
N5 C16 H16B . . 109.5
H16A C16 H16B . . 109.5
N5 C16 H16C . . 109.5
H16A C16 H16C . . 109.5
H16B C16 H16C . . 109.5
N5 C17 H17A . . 109.5
N5 C17 H17B . . 109.5
H17A C17 H17B . . 109.5
N5 C17 H17C . . 109.5
H17A C17 H17C . . 109.5
H17B C17 H17C . . 109.5
O2 C18 N5 . . 144.3(16)
O2 C18 H18 . . 107.9
N5 C18 H18 . . 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C4 . 1.723(6)
Cl2 C6 . 1.718(7)
O1 C12 . 1.205(7)
O2 C18 . 1.144(12)
F1 C1 . 1.253(11)
F2 C1 . 1.364(13)
F3 C1 . 1.280(13)
N1 C10 . 1.348(7)
N1 N2 . 1.357(6)
N1 C5 . 1.422(7)
N2 C8 . 1.334(8)
N3 C11 . 1.122(8)
N4 C12 . 1.363(7)
N4 C10 . 1.394(7)
N4 H4 . 0.8600
N5 C18 . 1.239(11)
N5 C16 . 1.375(13)
N5 C17 . 1.425(16)
C1 C2 . 1.493(11)
C2 C7 . 1.350(10)
C2 C3 . 1.393(10)
C3 C4 . 1.376(9)
C3 H3 . 0.9300
C4 C5 . 1.364(8)
C5 C6 . 1.390(9)
C6 C7 . 1.384(9)
C7 H7 . 0.9300
C8 C9 . 1.384(8)
C8 C11 . 1.457(8)
C9 C10 . 1.377(8)
C9 H9 . 0.9300
C12 C13 . 1.507(8)
C13 C14 . 1.369(8)
C13 C15 . 1.384(8)
C14 C15 3_666 1.389(8)
C14 H14 . 0.9300
C15 C14 3_666 1.389(8)
C15 H15 . 0.9300
C16 H16A . 0.9600
C16 H16B . 0.9600
C16 H16C . 0.9600
C17 H17A . 0.9600
C17 H17B . 0.9600
C17 H17C . 0.9600
C18 H18 . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N4 H4 O2 0.86 2.07 2.878(7) 157
