#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/41/2204128.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_2204128
loop_
_publ_author_name
'Elgemeie, Galal H.'
'Jones, Peter G.'
_publ_section_title
;
 5-Amino-3-anilino-N-(chlorophenyl)-1H-pyrazole-4-carboxamide
 ethanol solvate
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1616
_journal_page_last               o1618
_journal_paper_doi               10.1107/S1600536804020689
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H14 Cl N5 O, C2 H6 O'
_chemical_formula_moiety         'C16 H14 Cl N5 O, C2 H6 O'
_chemical_formula_sum            'C18 H20 Cl N5 O2'
_chemical_formula_weight         373.84
_chemical_name_systematic
;
5-Amino-3-anilino-N-(chlorophenyl)-1H-pyrazole-4-carboxamide ethanol solvate
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.140(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6757(10)
_cell_length_b                   7.7798(9)
_cell_length_c                   21.919(2)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.5
_cell_measurement_theta_min      4.5
_cell_volume                     1797.4(3)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       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  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4927
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0346
_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)+(0.0484P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0778
_refine_ls_wR_factor_ref         0.0829
_reflns_number_gt                2349
_reflns_number_total             3167
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6501.cif
_cod_data_source_block           4
_cod_original_cell_volume        1797.3(3)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2204128
_cod_database_fobs_code          2204128
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
Cl 0.04477(5) 0.81766(7) 0.55036(2) 0.04214(16) Uani d . 1 Cl
O1 0.43047(11) 0.18838(16) 0.46327(5) 0.0275(3) Uani d . 1 O
N1 0.68056(14) 0.0993(2) 0.33798(7) 0.0285(4) Uani d . 1 N
H01 0.7241(17) 0.008(3) 0.3254(8) 0.033(5) Uiso d . 1 H
N2 0.67822(13) 0.25984(19) 0.31126(6) 0.0265(4) Uani d . 1 N
C3 0.60229(15) 0.3501(2) 0.34070(7) 0.0220(4) Uani d . 1 C
C4 0.55412(15) 0.2524(2) 0.38640(7) 0.0216(4) Uani d . 1 C
N3 0.59107(18) -0.0588(2) 0.41236(8) 0.0336(4) Uani d . 1 N
H031 0.638(2) -0.137(3) 0.4083(10) 0.047(7) Uiso d . 1 H
H032 0.5647(19) -0.052(3) 0.4476(10) 0.050(7) Uiso d . 1 H
N4 0.57055(14) 0.5226(2) 0.32321(6) 0.0240(3) Uani d . 1 N
H04 0.6374(18) 0.585(2) 0.3201(8) 0.030(5) Uiso d . 1 H
C5 0.60714(16) 0.0899(2) 0.38230(7) 0.0240(4) Uani d . 1 C
N5 0.41956(13) 0.4604(2) 0.42298(7) 0.0245(3) Uani d . 1 N
H05 0.4529(17) 0.525(3) 0.4001(9) 0.035(6) Uiso d . 1 H
C6 0.46426(15) 0.2960(2) 0.42783(7) 0.0219(4) Uani d . 1 C
C12 0.32742(15) 0.5377(2) 0.45327(7) 0.0220(4) Uani d . 1 C
C13 0.30879(16) 0.7143(2) 0.44522(8) 0.0262(4) Uani d . 1 C
H13 0.3569 0.7760 0.4196 0.031 Uiso calc R 1 H
C14 0.22138(16) 0.8007(2) 0.47397(8) 0.0280(4) Uani d . 1 C
H14 0.2094 0.9210 0.4682 0.034 Uiso calc R 1 H
C15 0.15153(16) 0.7103(3) 0.51121(8) 0.0281(4) Uani d . 1 C
C16 0.16619(17) 0.5353(3) 0.51826(8) 0.0309(4) Uani d . 1 C
H16 0.1159 0.4740 0.5430 0.037 Uiso calc R 1 H
C17 0.25357(16) 0.4478(3) 0.48956(8) 0.0291(4) Uani d . 1 C
H17 0.2632 0.3270 0.4946 0.035 Uiso calc R 1 H
C18 0.47317(15) 0.5411(2) 0.27066(7) 0.0238(4) Uani d . 1 C
C19 0.47697(17) 0.6765(2) 0.22992(8) 0.0296(4) Uani d . 1 C
H19 0.5442 0.7578 0.2368 0.036 Uiso calc R 1 H
C20 0.38189(18) 0.6928(3) 0.17892(8) 0.0341(5) Uani d . 1 C
H20 0.3846 0.7859 0.1511 0.041 Uiso calc R 1 H
C21 0.28401(18) 0.5762(3) 0.16814(9) 0.0337(5) Uani d . 1 C
H21 0.2204 0.5871 0.1328 0.040 Uiso calc R 1 H
C22 0.27925(18) 0.4431(3) 0.20932(9) 0.0361(5) Uani d . 1 C
H22 0.2113 0.3630 0.2026 0.043 Uiso calc R 1 H
C23 0.37284(17) 0.4255(3) 0.26036(8) 0.0307(4) Uani d . 1 C
H23 0.3685 0.3337 0.2886 0.037 Uiso calc R 1 H
C98 0.52162(19) 0.1041(3) 0.16055(9) 0.0384(5) Uani d . 1 C
H98A 0.5779 0.0086 0.1540 0.046 Uiso calc R 1 H
H98B 0.4420 0.0940 0.1316 0.046 Uiso calc R 1 H
H98C 0.5037 0.1003 0.2030 0.046 Uiso calc R 1 H
C99 0.58476(17) 0.2714(2) 0.14991(8) 0.0319(4) Uani d . 1 C
H99A 0.5936 0.2805 0.1058 0.038 Uiso calc R 1 H
H99B 0.5305 0.3675 0.1597 0.038 Uiso calc R 1 H
O99 0.70842(12) 0.28640(17) 0.18736(6) 0.0300(3) Uani d . 1 O
H099 0.7003(19) 0.283(3) 0.2245(10) 0.043(6) Uiso d . 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'
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
C5 N1 N2 112.53(15) y
C5 N1 H01 123.9(12) ?
N2 N1 H01 123.5(12) ?
C3 N2 N1 104.24(14) y
N2 C3 C4 112.42(16) ?
N2 C3 N4 120.68(15) ?
C4 C3 N4 126.79(15) ?
C5 C4 C3 104.13(14) ?
C5 C4 C6 124.33(15) ?
C3 C4 C6 131.45(16) ?
C5 N3 H031 117.6(16) ?
C5 N3 H032 117.7(15) ?
H031 N3 H032 116(2) ?
C3 N4 C18 115.06(14) ?
C3 N4 H04 112.5(12) ?
C18 N4 H04 112.2(12) ?
N1 C5 N3 122.07(17) ?
N1 C5 C4 106.67(15) ?
N3 C5 C4 131.20(16) ?
C6 N5 C12 128.81(15) ?
C6 N5 H05 116.0(14) ?
C12 N5 H05 115.1(14) ?
O1 C6 N5 123.50(15) ?
O1 C6 C4 121.29(16) ?
N5 C6 C4 115.19(15) ?
C17 C12 C13 118.93(16) ?
C17 C12 N5 123.83(17) ?
C13 C12 N5 117.23(15) ?
C14 C13 C12 120.98(16) ?
C14 C13 H13 119.5 ?
C12 C13 H13 119.5 ?
C13 C14 C15 119.24(17) ?
C13 C14 H14 120.4 ?
C15 C14 H14 120.4 ?
C16 C15 C14 120.51(16) ?
C16 C15 Cl 119.34(14) ?
C14 C15 Cl 120.15(15) ?
C15 C16 C17 120.53(17) ?
C15 C16 H16 119.7 ?
C17 C16 H16 119.7 ?
C16 C17 C12 119.77(18) ?
C16 C17 H17 120.1 ?
C12 C17 H17 120.1 ?
C19 C18 C23 119.23(16) ?
C19 C18 N4 120.23(16) ?
C23 C18 N4 120.54(16) ?
C18 C19 C20 119.65(17) ?
C18 C19 H19 120.2 ?
C20 C19 H19 120.2 ?
C21 C20 C19 121.02(18) ?
C21 C20 H20 119.5 ?
C19 C20 H20 119.5 ?
C20 C21 C22 119.23(17) ?
C20 C21 H21 120.4 ?
C22 C21 H21 120.4 ?
C21 C22 C23 120.43(18) ?
C21 C22 H22 119.8 ?
C23 C22 H22 119.8 ?
C22 C23 C18 120.41(17) ?
C22 C23 H23 119.8 ?
C18 C23 H23 119.8 ?
C99 C98 H98A 109.5 ?
C99 C98 H98B 109.5 ?
H98A C98 H98B 109.5 ?
C99 C98 H98C 109.5 ?
H98A C98 H98C 109.5 ?
H98B C98 H98C 109.5 ?
O99 C99 C98 112.00(15) ?
O99 C99 H99A 109.2 ?
C98 C99 H99A 109.2 ?
O99 C99 H99B 109.2 ?
C98 C99 H99B 109.2 ?
H99A C99 H99B 107.9 ?
C99 O99 H099 109.0(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C15 1.7448(17) ?
O1 C6 1.234(2) ?
N1 C5 1.344(2) ?
N1 N2 1.378(2) y
N1 H01 0.92(2) ?
N2 C3 1.316(2) ?
C3 C4 1.417(2) ?
C3 N4 1.422(2) ?
C4 C5 1.394(2) ?
C4 C6 1.462(2) ?
N3 C5 1.356(2) ?
N3 H031 0.81(2) ?
N3 H032 0.87(2) ?
N4 C18 1.431(2) ?
N4 H04 0.876(19) ?
N5 C6 1.363(2) ?
N5 C12 1.406(2) ?
N5 H05 0.83(2) ?
C12 C17 1.393(2) ?
C12 C13 1.396(2) ?
C13 C14 1.381(2) ?
C13 H13 0.9500 ?
C14 C15 1.383(2) ?
C14 H14 0.9500 ?
C15 C16 1.376(3) ?
C16 C17 1.384(3) ?
C16 H16 0.9500 ?
C17 H17 0.9500 ?
C18 C19 1.385(2) ?
C18 C23 1.390(2) ?
C19 C20 1.391(3) ?
C19 H19 0.9500 ?
C20 C21 1.376(3) ?
C20 H20 0.9500 ?
C21 C22 1.380(3) ?
C21 H21 0.9500 ?
C22 C23 1.383(2) ?
C22 H22 0.9500 ?
C23 H23 0.9500 ?
C98 C99 1.501(3) ?
C98 H98A 0.9800 ?
C98 H98B 0.9800 ?
C98 H98C 0.9800 ?
C99 O99 1.444(2) ?
C99 H99A 0.9900 ?
C99 H99B 0.9900 ?
O99 H099 0.83(2) ?
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
N3 H032 O1 . 0.87(2) 2.41(2) 2.914(2) 117.4(18)
N5 H05 N4 . 0.83(2) 2.26(2) 2.955(2) 142.0(18)
N1 H01 O99 2_645 0.92(2) 1.90(2) 2.801(2) 165.6(17)
N3 H032 O1 3_656 0.87(2) 2.22(2) 2.950(2) 142(2)
N4 H04 O99 2_655 0.876(19) 2.30(2) 3.163(2) 170.7(17)
O99 H099 N2 . 0.83(2) 1.96(2) 2.7928(19) 176(2)
C17 H17 O1 . 0.95 2.28 2.884(2) 121
C21 H21 O1 2 0.95 2.56 3.494(2) 167
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_publ_flag
C5 N1 N2 C3 0.60(19) ?
N1 N2 C3 C4 -0.05(18) ?
N1 N2 C3 N4 -176.45(14) ?
N2 C3 C4 C5 -0.47(19) ?
N4 C3 C4 C5 175.67(16) y
N2 C3 C4 C6 -177.17(16) ?
N4 C3 C4 C6 -1.0(3) y
N2 C3 N4 C18 80.3(2) ?
C4 C3 N4 C18 -95.58(19) ?
N2 N1 C5 N3 176.73(16) ?
N2 N1 C5 C4 -0.90(19) ?
C3 C4 C5 N1 0.80(18) ?
C6 C4 C5 N1 177.80(15) ?
C3 C4 C5 N3 -176.53(19) ?
C6 C4 C5 N3 0.5(3) ?
C12 N5 C6 O1 -2.6(3) ?
C12 N5 C6 C4 175.73(15) ?
C5 C4 C6 O1 1.0(3) ?
C3 C4 C6 O1 177.11(16) ?
C5 C4 C6 N5 -177.41(15) y
C3 C4 C6 N5 -1.3(3) ?
C6 N5 C12 C17 -8.0(3) y
C6 N5 C12 C13 173.07(16) ?
C17 C12 C13 C14 1.8(3) ?
N5 C12 C13 C14 -179.13(15) ?
C12 C13 C14 C15 0.0(3) ?
C13 C14 C15 C16 -1.8(3) ?
C13 C14 C15 Cl 177.60(13) ?
C14 C15 C16 C17 1.8(3) ?
Cl C15 C16 C17 -177.61(14) ?
C15 C16 C17 C12 0.1(3) ?
C13 C12 C17 C16 -1.8(3) ?
N5 C12 C17 C16 179.20(16) y
C3 N4 C18 C19 -145.85(16) ?
C3 N4 C18 C23 35.1(2) ?
C23 C18 C19 C20 -1.1(3) ?
N4 C18 C19 C20 179.82(16) ?
C18 C19 C20 C21 -0.2(3) ?
C19 C20 C21 C22 1.2(3) ?
C20 C21 C22 C23 -1.0(3) ?
C21 C22 C23 C18 -0.3(3) ?
C19 C18 C23 C22 1.4(3) ?
N4 C18 C23 C22 -179.59(16) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130535
