#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/20/2222060.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_2222060
loop_
_publ_author_name
'Zhang, Guo-Hua'
'Wu, Yong-Zhong'
'Li, Hao-Yuan'
'Liu, Bo-Nian'
'Guo, Cheng'
_publ_section_title
;
 Ethyl 3-nitro-4-(n-propylamino)benzoate
;
_journal_coeditor_code           HK2690
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1380
_journal_paper_doi               10.1107/S160053680901873X
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C12 H16 N2 O4'
_chemical_formula_moiety         'C12 H16 N2 O4'
_chemical_formula_sum            'C12 H16 N2 O4'
_chemical_formula_weight         252.27
_chemical_name_systematic
;
Ethyl 3-nitro-4-(n-propylamino)benzoate
;
_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                61.710(19)
_cell_angle_beta                 83.02(3)
_cell_angle_gamma                81.75(3)
_cell_formula_units_Z            2
_cell_length_a                   4.4400(9)
_cell_length_b                   12.606(3)
_cell_length_c                   13.209(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      11
_cell_measurement_theta_min      9
_cell_volume                     643.1(3)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.0833
_diffrn_reflns_av_sigmaI/netI    0.0860
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2593
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.75
_diffrn_standards_decay_%        1
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9902
_exptl_absorpt_correction_T_min  0.9805
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2281
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1695
_refine_ls_R_factor_gt           0.0669
_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)+(0.057P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1654
_reflns_number_gt                924
_reflns_number_total             2281
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2690.cif
_cod_data_source_block           I
_cod_database_code               2222060
_cod_database_fobs_code          2222060
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.3870(7) -0.0274(2) 0.8647(2) 0.0865(10) Uani d . 1 . .
O O2 -0.2837(8) -0.1310(3) 0.7632(3) 0.1130(12) Uani d . 1 . .
O O3 -0.0492(8) 0.3592(2) 0.7202(2) 0.1056(12) Uani d . 1 . .
O O4 0.2630(7) 0.4310(3) 0.5801(2) 0.104 Uani d D 1 . .
N N1 0.1072(8) 0.3526(3) 0.6413(3) 0.0706(10) Uani d . 1 . .
N N2 0.4396(8) 0.3293(3) 0.4457(3) 0.0842(11) Uani d U 1 . .
H H2A 0.4491 0.3936 0.4521 0.101 Uiso calc R 1 . .
C C1 -0.3968(13) -0.2145(4) 1.0388(4) 0.127(2) Uani d . 1 . .
H H1A -0.5267 -0.2746 1.0918 0.190 Uiso calc R 1 . .
H H1B -0.3079 -0.1811 1.0788 0.190 Uiso calc R 1 . .
H H1C -0.2379 -0.2511 1.0058 0.190 Uiso calc R 1 . .
C C2 -0.5738(10) -0.1193(4) 0.9484(4) 0.1006(16) Uani d . 1 . .
H H2B -0.7339 -0.0825 0.9819 0.121 Uiso calc R 1 . .
H H2C -0.6696 -0.1538 0.9100 0.121 Uiso calc R 1 . .
C C3 -0.2502(11) -0.0448(4) 0.7781(4) 0.0809(13) Uani d . 1 . .
C C4 -0.0655(9) 0.0540(3) 0.6944(3) 0.0664(11) Uani d . 1 . .
C C5 -0.0537(8) 0.1582(3) 0.7019(3) 0.0592(10) Uani d . 1 . .
H H5A -0.1638 0.1678 0.7620 0.071 Uiso calc R 1 . .
C C6 0.1163(8) 0.2486(3) 0.6230(3) 0.0584(10) Uani d . 1 . .
C C7 0.2859(8) 0.2413(3) 0.5268(3) 0.0588(10) Uani d . 1 . .
C C8 0.2554(10) 0.1315(4) 0.5233(3) 0.0820(13) Uani d . 1 . .
H H8A 0.3503 0.1217 0.4612 0.098 Uiso calc RD 1 . .
C C9 0.1030(11) 0.0445(4) 0.6018(4) 0.0834(14) Uani d . 1 . .
H H9A 0.1064 -0.0264 0.5961 0.100 Uiso calc R 1 . .
C C10 0.5976(13) 0.3193(4) 0.3427(4) 0.129(2) Uani d DU 1 . .
H H10A 0.8040 0.2821 0.3610 0.155 Uiso calc R 1 . .
H H10B 0.4927 0.2659 0.3281 0.155 Uiso calc RD 1 . .
C C11 0.6104(14) 0.4292(5) 0.2425(4) 0.138(2) Uani d DU 1 . .
H H11A 0.7199 0.4821 0.2561 0.165 Uiso calc R 1 . .
H H11B 0.4046 0.4674 0.2246 0.165 Uiso calc R 1 . .
C C12 0.7633(11) 0.4158(4) 0.1409(3) 0.1116(17) Uani d . 1 . .
H H12A 0.7768 0.4944 0.0758 0.167 Uiso calc R 1 . .
H H12B 0.6465 0.3692 0.1229 0.167 Uiso calc R 1 . .
H H12C 0.9645 0.3752 0.1591 0.167 Uiso calc R 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'
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 . . 117.2(3) ?
O4 N1 O3 . . 120.0(3) ?
O4 N1 C6 . . 119.2(3) ?
O3 N1 C6 . . 120.8(3) ?
C7 N2 C10 . . 121.4(4) ?
C7 N2 H2A . . 119.3 ?
C10 N2 H2A . . 119.3 ?
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 ?
C1 C2 O1 . . 111.7(4) ?
C1 C2 H2B . . 109.3 ?
O1 C2 H2B . . 109.3 ?
C1 C2 H2C . . 109.3 ?
O1 C2 H2C . . 109.3 ?
H2B C2 H2C . . 107.9 ?
O2 C3 O1 . . 123.7(4) ?
O2 C3 C4 . . 121.8(5) ?
O1 C3 C4 . . 114.4(4) ?
C5 C4 C9 . . 116.8(4) ?
C5 C4 C3 . . 122.8(4) ?
C9 C4 C3 . . 120.4(4) ?
C4 C5 C6 . . 121.8(3) ?
C4 C5 H5A . . 119.1 ?
C6 C5 H5A . . 119.1 ?
C5 C6 C7 . . 122.2(3) ?
C5 C6 N1 . . 115.8(3) ?
C7 C6 N1 . . 121.9(3) ?
N2 C7 C6 . . 123.9(4) ?
N2 C7 C8 . . 123.4(3) ?
C6 C7 C8 . . 112.6(3) ?
C9 C8 C7 . . 124.2(4) ?
C9 C8 H8A . . 117.9 ?
C7 C8 H8A . . 117.9 ?
C8 C9 C4 . . 122.3(4) ?
C8 C9 H9A . . 118.8 ?
C4 C9 H9A . . 118.8 ?
C11 C10 N2 . . 114.4(4) ?
C11 C10 H10A . . 108.7 ?
N2 C10 H10A . . 108.7 ?
C11 C10 H10B . . 108.7 ?
N2 C10 H10B . . 108.7 ?
H10A C10 H10B . . 107.6 ?
C10 C11 C12 . . 113.1(4) ?
C10 C11 H11A . . 109.0 ?
C12 C11 H11A . . 109.0 ?
C10 C11 H11B . . 109.0 ?
C12 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
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
O1 C3 . 1.326(5) ?
O1 C2 . 1.446(4) ?
O2 C3 . 1.223(4) ?
O3 N1 . 1.211(3) ?
O4 N1 . 1.188(3) ?
N1 C6 . 1.436(4) ?
N2 C7 . 1.326(4) ?
N2 C10 . 1.505(5) ?
N2 H2A . 0.8600 ?
C1 C2 . 1.443(5) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 H2B . 0.9700 ?
C2 H2C . 0.9700 ?
C3 C4 . 1.488(5) ?
C4 C5 . 1.372(4) ?
C4 C9 . 1.400(5) ?
C5 C6 . 1.373(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.432(4) ?
C7 C8 . 1.432(5) ?
C8 C9 . 1.304(5) ?
C8 H8A . 0.9300 ?
C9 H9A . 0.9300 ?
C10 C11 . 1.393(5) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.500(5) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9600 ?
C12 H12B . 0.9600 ?
C12 H12C . 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
N2 H2A O4 . 0.86 2.02 2.635(5) 128
N2 H2A O4 2_666 0.86 2.55 3.324(6) 150
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
C3 O1 C2 C1 . . . . 87.3(5) ?
C2 O1 C3 O2 . . . . 3.0(6) ?
C2 O1 C3 C4 . . . . 179.2(3) ?
O2 C3 C4 C5 . . . . 172.1(4) ?
O1 C3 C4 C5 . . . . -4.1(6) ?
O2 C3 C4 C9 . . . . -6.9(7) ?
O1 C3 C4 C9 . . . . 176.9(4) ?
C9 C4 C5 C6 . . . . -0.4(6) ?
C3 C4 C5 C6 . . . . -179.4(4) ?
C4 C5 C6 C7 . . . . 1.5(6) ?
C4 C5 C6 N1 . . . . 179.9(3) ?
C5 C6 C7 N2 . . . . 176.3(4) ?
N1 C6 C7 N2 . . . . -2.0(6) ?
C5 C6 C7 C8 . . . . 0.2(5) ?
N1 C6 C7 C8 . . . . -178.1(3) ?
N2 C7 C8 C9 . . . . -179.4(4) ?
C6 C7 C8 C9 . . . . -3.2(6) ?
C7 C8 C9 C4 . . . . 4.6(7) ?
C5 C4 C9 C8 . . . . -2.6(6) ?
C3 C4 C9 C8 . . . . 176.5(4) ?
C7 N2 C10 C11 . . . . 148.5(5) ?
N2 C10 C11 C12 . . . . -178.8(4) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17318137
