#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/02/2220216.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_2220216
loop_
_publ_author_name
'Li, Yan'
'Shao, Teng-Fei'
'Wang, Jian-Wu'
_publ_section_title
;
 Ethyl 5-amino-3-methylsulfanyl-1H-pyrazole-4-carboxylate
;
_journal_coeditor_code           HG2437
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2280
_journal_paper_doi               10.1107/S1600536808035095
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C7 H11 N3 O2 S'
_chemical_formula_moiety         'C7 H11 N3 O2 S'
_chemical_formula_sum            'C7 H11 N3 O2 S'
_chemical_formula_weight         201.25
_chemical_name_systematic
;
Ethyl 5-amino-3-methylsulfanyl-1H-pyrazole-4-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.038(2)
_cell_angle_beta                 72.173(2)
_cell_angle_gamma                65.6430(10)
_cell_formula_units_Z            2
_cell_length_a                   7.0012(7)
_cell_length_b                   7.5870(8)
_cell_length_c                   10.1055(10)
_cell_measurement_reflns_used    1750
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      2.95
_cell_volume                     465.26(8)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART 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  0.0132
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            2317
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.12
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.319
_exptl_absorpt_correction_T_max  0.9842
_exptl_absorpt_correction_T_min  0.9688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0441
_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)+(0.0669P)²+0.2967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1269
_reflns_number_gt                1488
_reflns_number_total             1624
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg2437.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_database_code               2220216
_cod_database_fobs_code          2220216
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_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
S S1 0.46271(10) 0.72168(10) 0.13781(7) 0.0506(3) Uani d . 1
O O1 0.3262(3) 0.7811(3) 0.61242(17) 0.0461(4) Uani d . 1
O O2 0.1914(3) 0.7558(3) 0.44317(18) 0.0486(5) Uani d . 1
N N2 0.8938(3) 0.7010(3) 0.3056(2) 0.0435(5) Uani d . 1
H H2C 1.0232 0.6889 0.3013 0.052 Uiso calc R 1
C C3 0.3414(4) 0.7574(3) 0.4801(2) 0.0383(5) Uani d . 1
N N1 0.7639(3) 0.7355(3) 0.5482(2) 0.0510(6) Uani d . 1
H H1D 0.8881 0.7260 0.5535 0.061 Uiso calc R 1
H H1E 0.6578 0.7515 0.6223 0.061 Uiso calc R 1
C C5 0.7355(3) 0.7256(3) 0.4242(2) 0.0368(5) Uani d . 1
C C2 0.1246(4) 0.8045(4) 0.7109(3) 0.0418(6) Uani d . 1
H H2A 0.0903 0.6923 0.7138 0.050 Uiso calc R 1
H H2B 0.0088 0.9182 0.6866 0.050 Uiso calc R 1
C C6 0.6221(4) 0.7165(3) 0.2425(3) 0.0387(5) Uani d . 1
N N3 0.8282(3) 0.6970(3) 0.1904(2) 0.0450(5) Uani d . 1
C C4 0.5518(3) 0.7352(3) 0.3906(2) 0.0360(5) Uani d . 1
C C1 0.1484(5) 0.8274(4) 0.8514(3) 0.0542(7) Uani d . 1
H H1A 0.0146 0.8433 0.9215 0.081 Uiso calc R 1
H H1B 0.1818 0.9392 0.8472 0.081 Uiso calc R 1
H H1C 0.2638 0.7143 0.8740 0.081 Uiso calc R 1
C C7 0.6528(5) 0.7014(5) -0.0316(3) 0.0626(8) Uani d . 1
H H7A 0.5843 0.7025 -0.1009 0.094 Uiso calc R 1
H H7B 0.7777 0.5824 -0.0347 0.094 Uiso calc R 1
H H7C 0.6977 0.8085 -0.0493 0.094 Uiso calc R 1
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
S1 0.0384(4) 0.0712(5) 0.0510(4) -0.0245(3) -0.0179(3) -0.0052(3)
O1 0.0381(9) 0.0649(11) 0.0429(9) -0.0248(8) -0.0141(7) -0.0026(8)
O2 0.0306(9) 0.0707(12) 0.0543(11) -0.0249(8) -0.0170(8) -0.0035(9)
N2 0.0280(9) 0.0626(13) 0.0486(12) -0.0232(9) -0.0139(8) -0.0029(9)
C3 0.0304(11) 0.0412(12) 0.0469(13) -0.0150(9) -0.0144(10) 0.0001(10)
N1 0.0336(11) 0.0840(16) 0.0477(12) -0.0301(11) -0.0154(9) -0.0060(11)
C5 0.0286(11) 0.0430(12) 0.0450(12) -0.0174(9) -0.0143(9) -0.0002(10)
C2 0.0311(11) 0.0468(13) 0.0547(14) -0.0174(10) -0.0189(10) -0.0003(11)
C6 0.0324(11) 0.0389(12) 0.0460(13) -0.0151(9) -0.0100(10) -0.0022(9)
N3 0.0335(10) 0.0597(13) 0.0463(12) -0.0218(9) -0.0105(9) -0.0043(9)
C4 0.0254(10) 0.0398(11) 0.0475(13) -0.0141(9) -0.0141(9) -0.0016(9)
C1 0.0513(15) 0.0736(18) 0.0446(14) -0.0320(14) -0.0093(12) -0.0064(13)
C7 0.0547(17) 0.095(2) 0.0483(16) -0.0347(16) -0.0180(13) -0.0050(15)
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'
S S 0.1246 0.1234 '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
C6 S1 C7 100.66(12)
C3 O1 C2 116.79(18)
C5 N2 N3 113.11(18)
C5 N2 H2C 123.4
N3 N2 H2C 123.4
O2 C3 O1 123.1(2)
O2 C3 C4 125.2(2)
O1 C3 C4 111.67(19)
C5 N1 H1D 120.0
C5 N1 H1E 120.0
H1D N1 H1E 120.0
N2 C5 N1 122.8(2)
N2 C5 C4 107.0(2)
N1 C5 C4 130.2(2)
O1 C2 C1 106.85(18)
O1 C2 H2A 110.4
C1 C2 H2A 110.4
O1 C2 H2B 110.4
C1 C2 H2B 110.4
H2A C2 H2B 108.6
N3 C6 C4 111.9(2)
N3 C6 S1 122.18(19)
C4 C6 S1 125.90(17)
C6 N3 N2 104.02(19)
C5 C4 C3 129.2(2)
C5 C4 C6 103.93(19)
C3 C4 C6 126.9(2)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
S1 C7 H7A 109.5
S1 C7 H7B 109.5
H7A C7 H7B 109.5
S1 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C6 1.744(2)
S1 C7 1.801(3)
O1 C3 1.343(3)
O1 C2 1.415(3)
O2 C3 1.222(3)
N2 C5 1.336(3)
N2 N3 1.385(3)
N2 H2C 0.8600
C3 C4 1.429(3)
N1 C5 1.346(3)
N1 H1D 0.8600
N1 H1E 0.8600
C5 C4 1.399(3)
C2 C1 1.522(3)
C2 H2A 0.9700
C2 H2B 0.9700
C6 N3 1.328(3)
C6 C4 1.435(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
N1 H1D O2 1_655 0.86 2.16 2.914(3) 146.0
N2 H2C O2 1_655 0.86 2.34 3.019(3) 136.7
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
C2 O1 C3 O2 0.2(3)
C2 O1 C3 C4 -179.98(19)
N3 N2 C5 N1 -179.3(2)
N3 N2 C5 C4 1.3(3)
C3 O1 C2 C1 179.7(2)
C7 S1 C6 N3 -1.3(2)
C7 S1 C6 C4 177.5(2)
C4 C6 N3 N2 0.6(3)
S1 C6 N3 N2 179.63(16)
C5 N2 N3 C6 -1.2(3)
N2 C5 C4 C3 178.9(2)
N1 C5 C4 C3 -0.4(4)
N2 C5 C4 C6 -0.8(2)
N1 C5 C4 C6 179.9(2)
O2 C3 C4 C5 -176.5(2)
O1 C3 C4 C5 3.6(3)
O2 C3 C4 C6 3.1(4)
O1 C3 C4 C6 -176.7(2)
N3 C6 C4 C5 0.1(3)
S1 C6 C4 C5 -178.88(17)
N3 C6 C4 C3 -179.6(2)
S1 C6 C4 C3 1.4(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 742557
