#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/23/2222350.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_2222350
loop_
_publ_author_name
'Tan, Hai-Jun'
'He, Hai-Bing'
'Xia, Ming'
'Zhang, Xiang-Ning'
'Zhu, Hong-Jun'
_publ_section_title
;
 Ethyl 2-(3-chloro-2-pyridyl)-5-oxopyrazolidine-3-carboxylate
;
_journal_coeditor_code           HK2697
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1495
_journal_paper_doi               10.1107/S1600536809020789
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C11 H12 Cl N3 O3'
_chemical_formula_sum            'C11 H12 Cl N3 O3'
_chemical_formula_weight         269.69
_chemical_name_systematic
;
Ethyl 2-(3-chloro-2-pyridyl)-5-oxopyrazolidine-3-carboxylate
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   15.488(3)
_cell_length_b                   10.009(2)
_cell_length_c                   16.249(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      0.970
_cell_measurement_theta_min      0.913
_cell_volume                     2518.9(8)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4 diffractometer'
_diffrn_measurement_method       'ω/2θ 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  0.0293
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4453
_diffrn_reflns_theta_full        25.26
_diffrn_reflns_theta_max         25.26
_diffrn_reflns_theta_min         2.51
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.308
_exptl_absorpt_correction_T_max  0.9699
_exptl_absorpt_correction_T_min  0.9134
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.233
_refine_ls_extinction_coef       0.0065(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0429
_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)+(0.0473P)²+0.8240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1101
_reflns_number_gt                1635
_reflns_number_total             2273
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2697.cif
_cod_data_source_block           I
_cod_database_code               2222350
_cod_database_fobs_code          2222350
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl 0.45523(4) 0.14184(7) 0.43566(5) 0.0629(3) Uani d . 1 . .
O O1 0.30427(10) 0.43898(19) 0.31272(11) 0.0561(5) Uani d . 1 . .
O O2 0.34478(11) 0.4578(2) 0.44373(11) 0.0597(5) Uani d . 1 . .
O O3 0.55616(12) 0.7407(2) 0.33051(13) 0.0667(6) Uani d . 1 . .
N N1 0.54947(12) 0.55100(18) 0.40815(12) 0.0372(5) Uani d . 1 . .
H H1A 0.5776 0.5814 0.4497 0.045 Uiso calc R 1 . .
N N2 0.51613(11) 0.41865(17) 0.40548(11) 0.0328(4) Uani d . 1 . .
N N3 0.66149(12) 0.3566(2) 0.37919(13) 0.0456(5) Uani d . 1 . .
C C1 0.1756(2) 0.3232(4) 0.3592(2) 0.0876(11) Uani d . 1 . .
H H1B 0.1163 0.3358 0.3745 0.131 Uiso calc R 1 . .
H H1C 0.2069 0.2863 0.4049 0.131 Uiso calc R 1 . .
H H1D 0.1789 0.2631 0.3133 0.131 Uiso calc R 1 . .
C C2 0.21401(15) 0.4539(3) 0.3359(2) 0.0666(9) Uani d . 1 . .
H H2A 0.1820 0.4915 0.2902 0.080 Uiso calc R 1 . .
H H2B 0.2096 0.5152 0.3820 0.080 Uiso calc R 1 . .
C C3 0.36204(14) 0.4419(2) 0.37295(15) 0.0389(6) Uani d . 1 . .
C C4 0.45184(14) 0.4216(2) 0.33772(13) 0.0363(5) Uani d . 1 . .
H H4A 0.4542 0.3381 0.3063 0.044 Uiso calc R 1 . .
C C5 0.48079(15) 0.5388(3) 0.28374(15) 0.0471(6) Uani d . 1 . .
H H5A 0.5154 0.5078 0.2378 0.056 Uiso calc R 1 . .
H H5B 0.4315 0.5878 0.2627 0.056 Uiso calc R 1 . .
C C6 0.53378(15) 0.6246(3) 0.34130(15) 0.0434(6) Uani d . 1 . .
C C7 0.58184(14) 0.3194(2) 0.39697(13) 0.0332(5) Uani d . 1 . .
C C8 0.72260(16) 0.2612(3) 0.37550(18) 0.0565(8) Uani d . 1 . .
H H8A 0.7790 0.2872 0.3639 0.068 Uiso calc R 1 . .
C C9 0.70658(18) 0.1279(3) 0.38781(17) 0.0548(7) Uani d . 1 . .
H H9A 0.7509 0.0655 0.3842 0.066 Uiso calc R 1 . .
C C10 0.62367(17) 0.0884(3) 0.40552(16) 0.0490(6) Uani d . 1 . .
H H10A 0.6104 -0.0013 0.4134 0.059 Uiso calc R 1 . .
C C11 0.56048(14) 0.1858(2) 0.41127(15) 0.0389(6) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O1 C2 . . 117.0(2) ?
N2 N1 H1A . . 122.5 ?
C6 N1 N2 . . 115.02(19) ?
C6 N1 H1A . . 122.5 ?
N1 N2 C7 . . 113.08(17) ?
N1 N2 C4 . . 104.33(16) ?
C7 N2 C4 . . 114.82(17) ?
C7 N3 C8 . . 117.8(2) ?
C2 C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C2 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
O1 C2 C1 . . 111.1(2) ?
O1 C2 H2A . . 109.4 ?
C1 C2 H2A . . 109.4 ?
O1 C2 H2B . . 109.4 ?
C1 C2 H2B . . 109.4 ?
H2A C2 H2B . . 108.0 ?
O2 C3 O1 . . 124.3(2) ?
O2 C3 C4 . . 126.0(2) ?
O1 C3 C4 . . 109.70(19) ?
N2 C4 C3 . . 109.73(17) ?
N2 C4 C5 . . 104.11(18) ?
C3 C4 C5 . . 112.46(19) ?
N2 C4 H4A . . 110.1 ?
C3 C4 H4A . . 110.1 ?
C5 C4 H4A . . 110.1 ?
C6 C5 C4 . . 103.85(18) ?
C6 C5 H5A . . 111.0 ?
C4 C5 H5A . . 111.0 ?
C6 C5 H5B . . 111.0 ?
C4 C5 H5B . . 111.0 ?
H5A C5 H5B . . 109.0 ?
O3 C6 N1 . . 126.0(2) ?
O3 C6 C5 . . 127.1(2) ?
N1 C6 C5 . . 106.8(2) ?
N3 C7 C11 . . 121.9(2) ?
N3 C7 N2 . . 119.3(2) ?
C11 C7 N2 . . 118.7(2) ?
N3 C8 C9 . . 123.8(2) ?
N3 C8 H8A . . 118.1 ?
C9 C8 H8A . . 118.1 ?
C8 C9 C10 . . 118.6(2) ?
C8 C9 H9A . . 120.7 ?
C10 C9 H9A . . 120.7 ?
C9 C10 C11 . . 118.2(2) ?
C9 C10 H10A . . 120.9 ?
C11 C10 H10A . . 120.9 ?
C10 C11 C7 . . 119.7(2) ?
C10 C11 Cl . . 120.06(19) ?
C7 C11 Cl . . 120.25(17) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C11 . 1.735(2) ?
O1 C2 . 1.456(3) ?
O1 C3 . 1.326(3) ?
O2 C3 . 1.191(3) ?
O3 C6 . 1.226(3) ?
N1 N2 . 1.422(2) ?
N1 C6 . 1.335(3) ?
N1 H1A . 0.8600 ?
N2 C4 . 1.485(3) ?
N2 C7 . 1.429(3) ?
N3 C7 . 1.321(3) ?
N3 C8 . 1.346(3) ?
C1 C2 . 1.485(4) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 C4 . 1.518(3) ?
C4 C5 . 1.531(3) ?
C4 H4A . 0.9800 ?
C5 C6 . 1.512(4) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C7 C11 . 1.396(3) ?
C8 C9 . 1.372(4) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.374(4) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.385(3) ?
C10 H10A . 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1A O2 5_666 0.86 2.14 2.910(3) 149 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 N1 N2 C7 . . . . 108.8(2) ?
C6 N1 N2 C4 . . . . -16.6(2) ?
C3 O1 C2 C1 . . . . -85.7(3) ?
C2 O1 C3 O2 . . . . -1.2(4) ?
C2 O1 C3 C4 . . . . 178.6(2) ?
N1 N2 C4 C3 . . . . -97.1(2) ?
C7 N2 C4 C3 . . . . 138.54(19) ?
N1 N2 C4 C5 . . . . 23.4(2) ?
C7 N2 C4 C5 . . . . -100.9(2) ?
O2 C3 C4 N2 . . . . 2.4(3) ?
O1 C3 C4 N2 . . . . -177.44(18) ?
O2 C3 C4 C5 . . . . -113.0(3) ?
O1 C3 C4 C5 . . . . 67.2(2) ?
N2 C4 C5 C6 . . . . -22.5(2) ?
C3 C4 C5 C6 . . . . 96.2(2) ?
N2 N1 C6 O3 . . . . 179.8(2) ?
N2 N1 C6 C5 . . . . 1.8(3) ?
C4 C5 C6 O3 . . . . -164.6(2) ?
C4 C5 C6 N1 . . . . 13.3(2) ?
C8 N3 C7 C11 . . . . -0.3(3) ?
C8 N3 C7 N2 . . . . 176.9(2) ?
N1 N2 C7 N3 . . . . -10.9(3) ?
C4 N2 C7 N3 . . . . 108.6(2) ?
N1 N2 C7 C11 . . . . 166.3(2) ?
C4 N2 C7 C11 . . . . -74.1(3) ?
C7 N3 C8 C9 . . . . 1.1(4) ?
N3 C8 C9 C10 . . . . -0.5(4) ?
C8 C9 C10 C11 . . . . -0.9(4) ?
C9 C10 C11 C7 . . . . 1.7(4) ?
C9 C10 C11 Cl . . . . -178.6(2) ?
N3 C7 C11 C10 . . . . -1.1(4) ?
N2 C7 C11 C10 . . . . -178.3(2) ?
N3 C7 C11 Cl . . . . 179.22(18) ?
N2 C7 C11 Cl . . . . 2.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11307670
