#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/36/2213625.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_2213625
loop_
_publ_author_name
'Liu, Wei'
'Guo, Yan-Ling'
'Han, Cong'
'Cheng, Shao-Ling'
_publ_section_title
;
 1-(4-Nitrophenyl)pyrrolidine-2-carboxamide
;
_journal_coeditor_code           YA2040
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2778
_journal_page_last               o2779
_journal_paper_doi               10.1107/S1600536807020120
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C11 H13 N3 O3'
_chemical_formula_moiety         'C11 H13 N3 O3'
_chemical_formula_sum            'C11 H13 N3 O3'
_chemical_formula_weight         235.24
_chemical_name_systematic
;
1-(4-Nitrophenyl)pyrrolidine-2-carboxamide
;
_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                   9.4711(14)
_cell_length_b                   13.1959(16)
_cell_length_c                   17.773(4)
_cell_measurement_reflns_used    52
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      18.9
_cell_measurement_theta_min      2.3
_cell_volume                     2221.3(7)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Bruker, 1997)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Bruker, 1997)'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       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  0.032
_diffrn_reflns_av_sigmaI/netI    0.042
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2508
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.10
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.18
_refine_ls_extinction_coef       0.0066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.06
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1915
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.06
_refine_ls_R_factor_all          0.092
_refine_ls_R_factor_gt           0.048
_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)+(0.001P)²+2P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.091
_refine_ls_wR_factor_ref         0.123
_reflns_number_gt                1083
_reflns_number_total             1915
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ya2040.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_torsion_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 (8 times).

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 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_torsion_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 (8
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2221.2(6)
_cod_database_code               2213625
_cod_database_fobs_code          2213625
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
O O1 0.7452(2) 0.51362(17) 0.76870(13) 0.0749(7) Uani d . 1
O O2 0.5309(3) 0.8194(2) 0.44972(15) 0.0941(9) Uani d . 1
O O3 0.7028(3) 0.7566(2) 0.38487(15) 0.1018(9) Uani d . 1
N N1 0.5211(3) 0.52956(19) 0.80850(14) 0.0698(8) Uani d . 1
H H1A 0.5375 0.5735 0.8463 0.084 Uiso calc R 1
H H1B 0.4276 0.5184 0.8052 0.084 Uiso calc R 1
N N2 0.6494(3) 0.42434(18) 0.63549(13) 0.0600(7) Uani d . 1
N N3 0.6188(3) 0.7524(2) 0.43813(16) 0.0748(8) Uani d . 1
C C1 0.6202(3) 0.4928(2) 0.76303(17) 0.0571(7) Uani d . 1
C C2 0.5670(3) 0.4174(2) 0.70433(15) 0.0558(7) Uani d . 1
H H2A 0.4666 0.4287 0.6938 0.067 Uiso calc R 1
C C3 0.5922(4) 0.3079(2) 0.73032(19) 0.0720(9) Uani d . 1
H H3A 0.5965 0.3042 0.7848 0.086 Uiso calc R 1
H H3B 0.5173 0.2638 0.7127 0.086 Uiso calc R 1
C C4 0.7302(4) 0.2787(3) 0.6963(2) 0.0852(11) Uani d . 1
H H4A 0.7318 0.2067 0.6854 0.102 Uiso calc R 1
H H4B 0.8070 0.2942 0.7305 0.102 Uiso calc R 1
C C5 0.7451(3) 0.3387(2) 0.62513(18) 0.0676(9) Uani d . 1
H H5A 0.8415 0.3617 0.6184 0.081 Uiso calc R 1
H H5B 0.7178 0.2986 0.5818 0.081 Uiso calc R 1
C C6 0.6415(3) 0.5038(2) 0.58735(16) 0.0545(7) Uani d . 1
C C7 0.7315(3) 0.5109(2) 0.52425(16) 0.0652(8) Uani d . 1
H H7A 0.7978 0.4602 0.5155 0.078 Uiso calc R 1
C C8 0.7229(4) 0.5911(2) 0.47584(17) 0.0684(9) Uani d . 1
H H8A 0.7832 0.5948 0.4346 0.082 Uiso calc R 1
C C9 0.6248(3) 0.6664(2) 0.48817(17) 0.0608(8) Uani d . 1
C C10 0.5344(3) 0.6614(2) 0.54885(17) 0.0623(8) Uani d . 1
H H10A 0.4685 0.7126 0.5564 0.075 Uiso calc R 1
C C11 0.5408(3) 0.5818(2) 0.59797(16) 0.0590(8) Uani d . 1
H H11A 0.4788 0.5789 0.6385 0.071 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
O1 0.0535(13) 0.0836(15) 0.0876(15) -0.0028(11) -0.0049(12) -0.0150(13)
O2 0.109(2) 0.0778(17) 0.0958(19) 0.0045(16) -0.0086(17) 0.0215(15)
O3 0.112(2) 0.115(2) 0.0776(16) -0.0166(18) 0.0085(17) 0.0248(16)
N1 0.0652(16) 0.0759(18) 0.0683(16) 0.0056(14) 0.0043(14) -0.0201(14)
N2 0.0662(16) 0.0553(14) 0.0586(15) 0.0095(13) 0.0055(13) -0.0024(12)
N3 0.086(2) 0.0769(19) 0.0612(17) -0.0176(18) -0.0130(17) 0.0071(16)
C1 0.0575(18) 0.0555(17) 0.0581(17) 0.0048(15) -0.0027(15) -0.0022(15)
C2 0.0593(17) 0.0531(16) 0.0551(16) 0.0012(14) 0.0023(14) -0.0049(14)
C3 0.082(2) 0.0564(18) 0.078(2) -0.0002(17) 0.0032(19) 0.0026(17)
C4 0.086(2) 0.068(2) 0.102(3) 0.0183(19) 0.010(2) 0.013(2)
C5 0.067(2) 0.0595(18) 0.076(2) 0.0108(16) 0.0004(18) -0.0096(17)
C6 0.0568(17) 0.0555(17) 0.0511(16) -0.0017(14) -0.0047(14) -0.0091(14)
C7 0.069(2) 0.0663(19) 0.0606(18) 0.0038(16) 0.0086(16) -0.0080(16)
C8 0.076(2) 0.074(2) 0.0558(18) -0.0118(18) 0.0061(17) -0.0050(17)
C9 0.0688(19) 0.0610(18) 0.0525(17) -0.0107(16) -0.0093(16) 0.0013(15)
C10 0.0645(19) 0.0606(19) 0.0618(19) -0.0026(16) -0.0074(16) -0.0061(16)
C11 0.0631(18) 0.0602(18) 0.0536(17) 0.0006(15) -0.0012(15) -0.0044(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 H1A 124.5
C1 N1 H1B 126.5
H1A N1 H1B 108.9
C6 N2 C2 123.4(2)
C6 N2 C5 123.6(3)
C2 N2 C5 113.0(2)
O2 N3 O3 122.0(3)
O2 N3 C9 119.2(3)
O3 N3 C9 118.8(3)
O1 C1 N1 123.5(3)
O1 C1 C2 121.6(3)
N1 C1 C2 114.8(3)
N2 C2 C1 110.9(2)
N2 C2 C3 103.2(2)
C1 C2 C3 110.9(2)
N2 C2 H2A 110.5
C1 C2 H2A 110.5
C3 C2 H2A 110.5
C4 C3 C2 104.9(3)
C4 C3 H3A 110.8
C2 C3 H3A 110.8
C4 C3 H3B 110.8
C2 C3 H3B 110.8
H3A C3 H3B 108.8
C3 C4 C5 106.8(3)
C3 C4 H4A 110.4
C5 C4 H4A 110.4
C3 C4 H4B 110.4
C5 C4 H4B 110.4
H4A C4 H4B 108.6
N2 C5 C4 104.1(3)
N2 C5 H5A 110.9
C4 C5 H5A 110.9
N2 C5 H5B 110.9
C4 C5 H5B 110.9
H5A C5 H5B 109.0
N2 C6 C7 121.3(3)
N2 C6 C11 121.0(3)
C7 C6 C11 117.7(3)
C8 C7 C6 121.1(3)
C8 C7 H7A 119.5
C6 C7 H7A 119.5
C7 C8 C9 119.9(3)
C7 C8 H8A 120.0
C9 C8 H8A 120.0
C8 C9 C10 120.6(3)
C8 C9 N3 119.7(3)
C10 C9 N3 119.7(3)
C11 C10 C9 120.6(3)
C11 C10 H10A 119.7
C9 C10 H10A 119.7
C10 C11 C6 120.2(3)
C10 C11 H11A 119.9
C6 C11 H11A 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.220(3)
O2 N3 1.232(4)
O3 N3 1.238(4)
N1 C1 1.330(4)
N1 H1A 0.90
N1 H1B 0.90
N2 C6 1.355(3)
N2 C2 1.454(3)
N2 C5 1.460(4)
N3 C9 1.443(4)
C1 C2 1.527(4)
C2 C3 1.536(4)
C2 H2A 0.98
C3 C4 1.491(4)
C3 H3A 0.97
C3 H3B 0.97
C4 C5 1.498(4)
C4 H4A 0.97
C4 H4B 0.97
C5 H5A 0.97
C5 H5B 0.97
C6 C7 1.412(4)
C6 C11 1.416(4)
C7 C8 1.366(4)
C7 H7A 0.93
C8 C9 1.378(4)
C8 H8A 0.93
C9 C10 1.379(4)
C10 C11 1.367(4)
C10 H10A 0.93
C11 H11A 0.93
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 H1B O1 6_557 0.90 2.17 2.959(3) 145.8
N1 H1A O2 7_576 0.90 2.32 3.206(3) 168.1
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
_geom_torsion_publ_flag
C6 N2 C2 C1 -71.2(3) ?
C5 N2 C2 C1 106.6(3) yes
C6 N2 C2 C3 170.0(3) ?
C5 N2 C2 C3 -12.1(3) ?
O1 C1 C2 N2 -35.0(4) ?
N1 C1 C2 N2 147.8(3) ?
O1 C1 C2 C3 79.1(4) yes
N1 C1 C2 C3 -98.2(3) yes
N2 C2 C3 C4 24.7(3) yes
C1 C2 C3 C4 -94.1(3) ?
C2 C3 C4 C5 -28.8(4) yes
C6 N2 C5 C4 172.6(3) ?
C2 N2 C5 C4 -5.2(4) yes
C3 C4 C5 N2 21.2(4) yes
C2 N2 C6 C7 175.0(3) ?
C5 N2 C6 C7 -2.7(4) yes
C2 N2 C6 C11 -6.1(4) ?
C5 N2 C6 C11 176.2(3) ?
N2 C6 C7 C8 179.9(3) ?
C11 C6 C7 C8 0.9(4) ?
C6 C7 C8 C9 -0.2(5) ?
C7 C8 C9 C10 -0.4(5) ?
C7 C8 C9 N3 178.2(3) ?
O2 N3 C9 C8 -179.9(3) ?
O3 N3 C9 C8 -0.1(4) ?
O2 N3 C9 C10 -1.3(4) ?
O3 N3 C9 C10 178.5(3) ?
C8 C9 C10 C11 0.2(4) ?
N3 C9 C10 C11 -178.4(3) ?
C9 C10 C11 C6 0.6(4) ?
N2 C6 C11 C10 180.0(3) ?
C7 C6 C11 C10 -1.1(4) ?
