#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/80/2208081.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_2208081
loop_
_publ_author_name
'Zdeněk Trávníček'
'Jaromír Marek'
'Petr Cankař'
_publ_section_title
;
 5-Amino-1-phenyl-1H-pyrazole
;
_journal_coeditor_code           HG6297
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o851
_journal_page_last               o853
_journal_paper_doi               10.1107/S160053680600290X
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C9 H9 N3'
_chemical_formula_moiety         'C9 H9 N3'
_chemical_formula_sum            'C9 H9 N3'
_chemical_formula_weight         159.19
_chemical_melting_point          315.0(10)
_chemical_name_systematic
;
1-Phenyl-5-amino-1H-pyrazole
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 128.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.386(3)
_cell_length_b                   14.056(3)
_cell_length_c                   10.462(2)
_cell_measurement_reflns_used    1962
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      26.565
_cell_measurement_theta_min      2.322
_cell_volume                     1644.8(9)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED'
_computing_molecular_graphics    'ORTEPIII (Johnson & Burnett, 1996)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      105(2)
_diffrn_detector_area_resol_mean 16.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  'Enhance (Oxford Diffraction)'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6395
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1447
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0524
_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)+(0.08P)²+0.5P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1497
_reflns_number_gt                1289
_reflns_number_total             1447
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6297.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_bond_publ_flag' value 'No' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_angle_publ_flag' value 'No' changed to 'no' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (25 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Yes' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (7
times).

'_geom_bond_publ_flag' value 'No' changed to 'no' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (9
times).

'_geom_angle_publ_flag' value 'No' changed to 'no' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (25 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2208081
_cod_database_fobs_code          2208081
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
N1 0.15119(13) 0.17150(10) 0.59566(19) 0.0216(4) Uani d . 1 N
N2 0.22494(14) 0.22388(11) 0.7388(2) 0.0268(4) Uani d . 1 N
N3 -0.05751(15) 0.15777(12) 0.3606(2) 0.0338(5) Uani d . 1 N
H3A -0.0414 0.1172 0.3129 0.041 Uiso calc R 1 H
H3B -0.1319 0.1747 0.3113 0.041 Uiso calc R 1 H
C3 0.15000(18) 0.27681(13) 0.7413(2) 0.0284(5) Uani d . 1 C
H3C 0.1749 0.3206 0.8267 0.034 Uiso calc R 1 H
C4 0.03080(18) 0.26156(13) 0.6055(2) 0.0267(5) Uani d . 1 C
H4 -0.0377 0.2910 0.5824 0.032 Uiso calc R 1 H
C5 0.03370(16) 0.19483(13) 0.5124(2) 0.0224(5) Uani d . 1 C
C6 0.20184(16) 0.10683(13) 0.5499(2) 0.0218(5) Uani d . 1 C
C7 0.14489(17) 0.02078(13) 0.4752(2) 0.0258(5) Uani d . 1 C
H7 0.0747 0.0035 0.4601 0.031 Uiso calc R 1 H
C8 0.19142(17) -0.03962(13) 0.4227(2) 0.0281(5) Uani d . 1 C
H8 0.1513 -0.0973 0.3681 0.034 Uiso calc R 1 H
C9 0.29591(17) -0.01613(14) 0.4497(2) 0.0298(5) Uani d . 1 C
H9 0.3274 -0.0574 0.4134 0.036 Uiso calc R 1 H
C10 0.35450(18) 0.06796(14) 0.5301(2) 0.0303(5) Uani d . 1 C
H10 0.4276 0.0832 0.5517 0.036 Uiso calc R 1 H
C11 0.30724(16) 0.12985(13) 0.5789(2) 0.0261(5) Uani d . 1 C
H11 0.3470 0.1879 0.6322 0.031 Uiso calc R 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0201(8) 0.0227(8) 0.0193(8) -0.0021(6) 0.0111(7) -0.0012(6)
N2 0.0268(9) 0.0277(9) 0.0218(9) -0.0057(7) 0.0133(8) -0.0050(7)
N3 0.0216(9) 0.0378(10) 0.0252(9) 0.0055(7) 0.0066(8) -0.0070(8)
C3 0.0338(11) 0.0271(10) 0.0271(11) -0.0040(8) 0.0205(10) -0.0066(8)
C4 0.0272(10) 0.0277(10) 0.0272(10) 0.0027(8) 0.0180(9) 0.0013(8)
C5 0.0218(10) 0.0235(9) 0.0201(10) 0.0000(7) 0.0122(8) 0.0030(7)
C6 0.0247(10) 0.0215(9) 0.0163(9) 0.0038(7) 0.0115(8) 0.0041(7)
C7 0.0282(10) 0.0227(10) 0.0256(10) 0.0011(8) 0.0164(9) 0.0029(8)
C8 0.0320(11) 0.0227(10) 0.0243(11) 0.0039(8) 0.0152(10) 0.0022(8)
C9 0.0333(11) 0.0290(11) 0.0261(11) 0.0107(9) 0.0182(10) 0.0049(9)
C10 0.0268(10) 0.0348(11) 0.0302(11) 0.0048(9) 0.0184(9) 0.0045(9)
C11 0.0248(10) 0.0249(10) 0.0251(10) -0.0007(8) 0.0139(9) 0.0009(8)
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'
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 111.16(15) yes
C5 N1 C6 128.91(16) yes
N2 N1 C6 119.87(15) yes
C3 N2 N1 103.94(15) yes
C5 N3 H3A 120.0 no
C5 N3 H3B 120.0 no
H3A N3 H3B 120.0 no
N2 C3 C4 112.89(17) yes
N2 C3 H3C 123.6 no
C4 C3 H3C 123.6 no
C5 C4 C3 105.17(17) yes
C5 C4 H4 127.4 no
C3 C4 H4 127.4 no
N1 C5 C4 106.80(17) yes
N1 C5 N3 122.91(17) yes
C4 C5 N3 130.21(17) yes
C11 C6 C7 120.19(17) no
C11 C6 N1 119.91(16) no
C7 C6 N1 119.90(17) no
C8 C7 C6 119.51(18) no
C8 C7 H7 120.2 no
C6 C7 H7 120.2 no
C9 C8 C7 120.32(18) no
C9 C8 H8 119.8 no
C7 C8 H8 119.8 no
C8 C9 C10 119.69(18) no
C8 C9 H9 120.2 no
C10 C9 H9 120.2 no
C11 C10 C9 120.46(18) no
C11 C10 H10 119.8 no
C9 C10 H10 119.8 no
C6 C11 C10 119.76(18) no
C6 C11 H11 120.1 no
C10 C11 H11 120.1 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C5 1.368(2) yes
N1 N2 1.383(2) yes
N1 C6 1.423(2) yes
N2 C3 1.324(3) yes
N3 C5 1.377(3) yes
N3 H3A 0.8800 no
N3 H3B 0.8800 no
C3 C4 1.393(3) yes
C3 H3C 0.9500 no
C4 C5 1.372(3) yes
C4 H4 0.9500 no
C6 C11 1.384(3) no
C6 C7 1.393(3) no
C7 C8 1.390(3) no
C7 H7 0.9500 no
C8 C9 1.384(3) no
C8 H8 0.9500 no
C9 C10 1.387(3) no
C9 H9 0.9500 no
C10 C11 1.385(3) no
C10 H10 0.9500 no
C11 H11 0.9500 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
N3 H3B N2 8_455 0.88 2.21 3.028(2) 155
C8 H8 C3 6 0.95 2.85 3.695(3) 149
C3 H3C C8 4_556 0.95 2.84 3.759(3) 162
N3 H3A C7 2 0.88 2.74 3.475(3) 142
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 63198
