#------------------------------------------------------------------------------
#$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/03/2010311.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_2010311
loop_
_publ_author_name
'Zukerman-Schpector, J.'
'Barreiro, E.J.'
'Freitas, A.C.C.'
_publ_section_title
;
 Structures of pyrazole derivatives. III.
 5-Amino-4-cyano-1-phenylpyrazole
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2095
_journal_page_last               2096
_journal_paper_doi               10.1107/S0108270193014556
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'Inlaid in SHELX76'
_cell_angle_alpha                90
_cell_angle_beta                 115.71(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.007(2)
_cell_length_b                   7.7260(10)
_cell_length_c                   12.194(2)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    292
_cell_measurement_theta_max      19
_cell_measurement_theta_min      7
_cell_volume                     934.3(3)
_diffrn_measurement_device       'Enraf-Nonius CAD4'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1389
_diffrn_reflns_theta_max         25
_diffrn_standards_decay_%        +-0.9
_diffrn_standards_interval_time  30
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellowish
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       irregular
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.33
_refine_ls_hydrogen_treatment    'one overall U~iso~ = 0.091(5)\%A^2^'
_refine_ls_number_parameters     128
_refine_ls_number_reflns         705
_refine_ls_R_factor_obs          0.0429
_refine_ls_shift/esd_max         0.001
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w=1/[\s^2^(|F~o~| + 0.0003|F~o~|^2^]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.0434
_reflns_number_observed          705
_reflns_number_total             1318
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            li1085.cif
_cod_data_source_block           li1085_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=1/[\s^2^(|F~o~| +
0.0003|F~o~|^2^]' was changed to 'calc'. New tag
'_refine_ls_weighting_details' was created. The value of the new tag
was set to 'w=1/[\s^2^(|F~o~| + 0.0003|F~o~|^2^]'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        934.3(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2010311
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
N(1) .0604(3) .1468(4) .2234(2)
N(2) .0778(4) .2215(4) .1277(3)
N(3) .1891(3) .0242(4) .4192(2)
N(4) .5303(4) .0928(6) .3936(3)
C(3) .2079(5) .2183(6) .1628(3)
C(4) .2772(4) .1424(5) .2782(3)
C(5) .1788(4) .0979(5) .3144(3)
C(6) .4170(5) .1145(6) .3422(4)
C(7) -.0721(4) .1321(5) .2144(3)
C(8) -.1022(4) .1905(5) .3065(3)
C(9) -.2331(5) .1820(6) .2914(4)
C(10) -.3323(4) .1189(6) .1855(5)
C(11) -.3008(5) .0600(6) .0943(4)
C(12) -.1704(4) .0656(5) .1075(3)
H(N3) .1025 -.0241 .4160
H(N3)' .2791 -.0275 .4790
H(C3) .2512 .2564 .1139
H(C8) -.0321 .2361 .3794
H(C9) -.2547 .2191 .3564
H(C10) -.4241 .1177 .1737
H(C11) -.3698 .0144 .0209
H(C12) -.1478 .0235 .0445
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
N(2) N(1) C(5) 111.8(3) yes
N(2) N(1) C(7) 118.7(3) yes
C(5) N(1) C(7) 129.4(3) yes
N(1) N(2) C(3) 104.4(3) yes
N(2) C(3) C(4) 112.2(4) yes
C(3) C(4) C(5) 105.3(4) yes
C(3) C(4) C(6) 127.4(4) yes
C(5) C(4) C(6) 127.3(4) yes
N(1) C(5) N(3) 123.2(3) yes
N(1) C(5) C(4) 106.2(3) yes
N(3) C(5) C(4) 130.5(3) yes
N(4) C(6) C(4) 179.6(5) yes
N(1) C(7) C(8) 120.9(4) yes
N(1) C(7) C(12) 117.4(3) yes
C(8) C(7) C(12) 121.6(4) yes
C(7) C(8) C(9) 119.0(4) yes
C(8) C(9) C(10) 120.3(4) yes
C(9) C(10) C(11) 120.1(5) yes
C(10) C(11) C(12) 120.7(4) yes
C(7) C(12) C(11) 118.2(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N(1) N(2) 1.388(5) yes
N(1) C(7) 1.419(6) yes
N(3) C(5) 1.358(4) yes
C(3) C(4) 1.405(5) yes
C(4) C(6) 1.408(7) yes
C(7) C(12) 1.382(5) yes
C(9) C(10) 1.369(7) yes
C(11) C(12) 1.374(7) yes
N(1) C(5) 1.348(5) yes
N(2) C(3) 1.305(7) yes
N(4) C(6) 1.139(7) yes
C(4) C(5) 1.379(6) yes
C(7) C(8) 1.377(6) yes
C(8) C(9) 1.373(8) yes
C(10) C(11) 1.378(7) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 79256