#------------------------------------------------------------------------------
#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/51/4505161.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4505161
loop_
_publ_author_name
'Kaftory, Menahem'
'Botoshansky, Mark'
'Sheinin, Yana'
_publ_section_title
;
 Dimormorphism and Cocrystal Formation of 3-(Chloroacetamido)pyrazole
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2242
_journal_paper_doi               10.1021/cg0501229
_journal_volume                  5
_journal_year                    2005
_chemical_formula_moiety         'C5 H6 Cl N3 O'
_chemical_formula_sum            'C5 H6 Cl N3 O'
_chemical_formula_weight         159.58
_chemical_name_common            Yana-370
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   23.830(5)
_cell_length_b                   23.830(5)
_cell_length_c                   5.196(1)
_cell_measurement_reflns_used    10380
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      1.71
_cell_volume                     2950.6(10)
_computing_cell_refinement       'DENZO SMN (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius, 2001)'
_computing_data_reduction        'DENZO SMN (Otwinowski & Minor 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'phi- and omega scans'
_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  0.10
_diffrn_reflns_av_sigmaI/netI    0.1130
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            9799
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.42
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.450
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0051(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.810
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         1280
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.810
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0488
_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)+(0.0805P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1465
_reflns_number_gt                546
_reflns_number_total             1253
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg0501229si20050621_074755.cif
_cod_data_source_block           yan370(2)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Tetragonal' changed to 'tetragonal'
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_sg_symbol_H-M      'I 41/a'
_cod_database_code               4505161
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Cl1 Cl 0.50601(6) 0.17328(5) 0.6632(2) 0.0988(7) Uani 1 1 d .
O1 O 0.41498(14) 0.09464(13) 0.5505(6) 0.0966(12) Uani 1 1 d .
N1 N 0.39057(16) -0.07601(15) 0.0793(7) 0.0788(12) Uani 1 1 d .
H1N H 0.3859 -0.1047 -0.0189 0.095 Uiso 1 1 calc R
N2 N 0.43367(15) -0.03970(15) 0.0575(6) 0.0678(10) Uani 1 1 d .
N3 N 0.46330(13) 0.04117(14) 0.2712(5) 0.0591(10) Uani 1 1 d .
H3N H 0.4941 0.0388 0.1859 0.071 Uiso 1 1 calc R
C1 C 0.42451(17) -0.00264(17) 0.2421(7) 0.0557(11) Uani 1 1 d .
C2 C 0.3765(2) -0.0151(2) 0.3811(8) 0.0751(14) Uani 1 1 d .
H2 H 0.3613 0.0044 0.5198 0.090 Uiso 1 1 calc R
C3 C 0.3567(2) -0.0625(2) 0.2674(10) 0.0802(14) Uani 1 1 d .
H3 H 0.3245 -0.0820 0.3152 0.096 Uiso 1 1 calc R
C4 C 0.4564(2) 0.08651(17) 0.4210(8) 0.0611(11) Uani 1 1 d .
C5 C 0.50560(19) 0.12621(16) 0.4076(7) 0.0676(12) Uani 1 1 d .
H5A H 0.5041 0.1469 0.2470 0.081 Uiso 1 1 calc R
H5B H 0.5402 0.1047 0.4092 0.081 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.1428(14) 0.0745(10) 0.0790(9) -0.0296(6) 0.0002(7) -0.0085(8)
O1 0.081(2) 0.083(2) 0.126(3) -0.039(2) 0.045(2) -0.0008(19)
N1 0.072(3) 0.071(3) 0.094(3) -0.023(2) 0.006(2) -0.019(2)
N2 0.066(3) 0.062(2) 0.076(2) -0.0217(19) 0.0085(19) -0.011(2)
N3 0.056(2) 0.058(2) 0.064(2) -0.0154(17) 0.0138(16) -0.0023(19)
C1 0.057(3) 0.052(3) 0.058(2) -0.002(2) 0.004(2) 0.001(2)
C2 0.078(4) 0.069(3) 0.078(3) -0.010(2) 0.023(3) -0.008(3)
C3 0.068(3) 0.073(4) 0.100(4) 0.001(3) 0.018(3) -0.011(3)
C4 0.070(3) 0.050(3) 0.063(2) -0.014(2) 0.002(2) 0.008(2)
C5 0.083(3) 0.047(3) 0.073(3) -0.022(2) 0.010(2) 0.000(3)
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 N1 N2 112.1(4)
C3 N1 H1N 124.0
N2 N1 H1N 124.0
C1 N2 N1 104.0(3)
C4 N3 C1 125.5(4)
C4 N3 H3N 117.2
C1 N3 H3N 117.2
N2 C1 C2 111.8(4)
N2 C1 N3 117.8(4)
C2 C1 N3 130.4(4)
C3 C2 C1 103.8(4)
C3 C2 H2 128.1
C1 C2 H2 128.1
N1 C3 C2 108.3(4)
N1 C3 H3 125.8
C2 C3 H3 125.8
O1 C4 N3 123.5(4)
O1 C4 C5 124.0(4)
N3 C4 C5 112.5(4)
C4 C5 Cl1 111.9(3)
C4 C5 H5A 109.2
Cl1 C5 H5A 109.2
C4 C5 H5B 109.2
Cl1 C5 H5B 109.2
H5A C5 H5B 107.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C5 1.738(3)
O1 C4 1.209(5)
N1 C3 1.308(5)
N1 N2 1.348(4)
N1 H1N 0.8600
N2 C1 1.322(5)
N3 C4 1.342(4)
N3 C1 1.402(5)
N3 H3N 0.8600
C1 C2 1.386(5)
C2 C3 1.359(6)
C2 H2 0.9300
C3 H3 0.9300
C4 C5 1.509(6)
C5 H5A 0.9700
C5 H5B 0.9700
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
C3 N1 N2 C1 -0.3(5)
N1 N2 C1 C2 0.3(5)
N1 N2 C1 N3 179.4(3)
C4 N3 C1 N2 169.6(4)
C4 N3 C1 C2 -11.6(7)
N2 C1 C2 C3 -0.2(5)
N3 C1 C2 C3 -179.1(4)
N2 N1 C3 C2 0.2(6)
C1 C2 C3 N1 0.0(5)
C1 N3 C4 O1 0.2(6)
C1 N3 C4 C5 -179.3(3)
O1 C4 C5 Cl1 17.6(6)
N3 C4 C5 Cl1 -162.9(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 53983407
