#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225686.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_2225686
loop_
_publ_author_name
'Abdul Rahim, Aisyah Saad'
'Abd Hamid, Shafida'
'Narendra Babu, Shivanagere Nagojappa'
'Loh, Wan-Sin'
'Fun, Hoong-Kun'
_publ_section_title
;
 Ethyl 4-(2-hydroxyethylamino)-3-nitrobenzoate
;
_journal_coeditor_code           WN2377
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o846
_journal_page_last               o847
_journal_paper_doi               10.1107/S1600536810008147
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H14 N2 O5'
_chemical_formula_moiety         'C11 H14 N2 O5'
_chemical_formula_sum            'C11 H14 N2 O5'
_chemical_formula_weight         254.24
_chemical_name_systematic
;
Ethyl 4-(2-hydroxyethylamino)-3-nitrobenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_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                 99.607(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6422(6)
_cell_length_b                   14.9954(9)
_cell_length_c                   7.1975(4)
_cell_measurement_reflns_used    1880
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.37
_cell_volume                     1132.50(11)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector diffractometer
;
_diffrn_measurement_method       'φ and ω 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  0.050
_diffrn_reflns_av_sigmaI/netI    0.0506
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8457
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.37
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_correction_T_min  0.9509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2090)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.313
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0511
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0602P)²+0.3204P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                2026
_reflns_number_total             2587
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn2377.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2225686
_cod_database_fobs_code          2225686
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.38669(15) 0.04338(11) 1.1300(3) 0.0285(4) Uani d . 1 . .
O O2 0.57298(13) 0.09227(10) 1.2508(2) 0.0193(4) Uani d . 1 . .
O O3 0.04479(14) 0.22764(10) 0.8325(2) 0.0194(4) Uani d . 1 . .
O O4 0.07343(13) 0.37665(10) 0.8413(2) 0.0170(4) Uani d . 1 . .
O O5 0.82105(15) 0.33071(11) 1.0883(2) 0.0192(4) Uani d . 1 . .
N N1 0.46108(17) 0.10564(12) 1.1729(3) 0.0157(4) Uani d . 1 . .
N N2 0.61527(17) 0.26565(12) 1.2825(3) 0.0147(4) Uani d . 1 . .
C C1 0.29266(19) 0.20462(14) 1.0362(3) 0.0141(5) Uani d . 1 . .
H H1A 0.2445 0.1539 0.9998 0.017 Uiso calc R 1 . .
C C2 0.4166(2) 0.19539(14) 1.1327(3) 0.0135(4) Uani d . 1 . .
C C3 0.49466(19) 0.27115(14) 1.1919(3) 0.0135(4) Uani d . 1 . .
C C4 0.43542(19) 0.35571(14) 1.1508(3) 0.0148(5) Uani d . 1 . .
H H4A 0.4811 0.4071 1.1901 0.018 Uiso calc R 1 . .
C C5 0.3135(2) 0.36374(14) 1.0555(3) 0.0148(5) Uani d . 1 . .
H H5A 0.2784 0.4202 1.0308 0.018 Uiso calc R 1 . .
C C6 0.2402(2) 0.28743(14) 0.9938(3) 0.0150(5) Uani d . 1 . .
C C7 0.11002(19) 0.29283(14) 0.8828(3) 0.0148(5) Uani d . 1 . .
C C8 -0.05110(19) 0.38757(14) 0.7226(3) 0.0168(5) Uani d . 1 . .
H H8A -0.1143 0.3517 0.7709 0.020 Uiso calc R 1 . .
H H8B -0.0473 0.3685 0.5949 0.020 Uiso calc R 1 . .
C C9 -0.0866(2) 0.48440(16) 0.7242(4) 0.0254(6) Uani d . 1 . .
H H9A -0.1695 0.4929 0.6501 0.038 Uiso calc R 1 . .
H H9B -0.0251 0.5192 0.6722 0.038 Uiso calc R 1 . .
H H9C -0.0879 0.5031 0.8515 0.038 Uiso calc R 1 . .
C C10 0.69687(19) 0.34151(14) 1.3465(3) 0.0142(4) Uani d . 1 . .
H H10A 0.7673 0.3210 1.4400 0.017 Uiso calc R 1 . .
H H10B 0.6484 0.3841 1.4073 0.017 Uiso calc R 1 . .
C C11 0.75012(19) 0.38863(14) 1.1886(3) 0.0157(5) Uani d . 1 . .
H H11A 0.6801 0.4141 1.1011 0.019 Uiso calc R 1 . .
H H11B 0.8047 0.4372 1.2419 0.019 Uiso calc R 1 . .
H H2A 0.642(2) 0.2141(18) 1.310(4) 0.021(7) Uiso d . 1 . .
H H5B 0.888(3) 0.3148(18) 1.156(4) 0.028(8) Uiso 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'
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
C7 O4 C8 . . 116.01(16) ?
C11 O5 H5B . . 110(2) ?
O1 N1 O2 . . 121.21(17) ?
O1 N1 C2 . . 118.86(17) ?
O2 N1 C2 . . 119.92(17) ?
C3 N2 C10 . . 125.21(19) ?
C3 N2 H2A . . 115.5(18) ?
C10 N2 H2A . . 119.1(18) ?
C6 C1 C2 . . 121.12(19) ?
C6 C1 H1A . . 119.4 ?
C2 C1 H1A . . 119.4 ?
C1 C2 C3 . . 121.68(19) ?
C1 C2 N1 . . 116.49(18) ?
C3 C2 N1 . . 121.82(19) ?
N2 C3 C4 . . 120.65(19) ?
N2 C3 C2 . . 123.9(2) ?
C4 C3 C2 . . 115.47(18) ?
C5 C4 C3 . . 122.1(2) ?
C5 C4 H4A . . 118.9 ?
C3 C4 H4A . . 118.9 ?
C4 C5 C6 . . 120.9(2) ?
C4 C5 H5A . . 119.5 ?
C6 C5 H5A . . 119.5 ?
C1 C6 C5 . . 118.61(19) ?
C1 C6 C7 . . 118.53(19) ?
C5 C6 C7 . . 122.85(19) ?
O3 C7 O4 . . 123.96(19) ?
O3 C7 C6 . . 123.46(19) ?
O4 C7 C6 . . 112.56(18) ?
O4 C8 C9 . . 107.99(17) ?
O4 C8 H8A . . 110.1 ?
C9 C8 H8A . . 110.1 ?
O4 C8 H8B . . 110.1 ?
C9 C8 H8B . . 110.1 ?
H8A C8 H8B . . 108.4 ?
C8 C9 H9A . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C8 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C10 C11 . . 113.65(18) ?
N2 C10 H10A . . 108.8 ?
C11 C10 H10A . . 108.8 ?
N2 C10 H10B . . 108.8 ?
C11 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
O5 C11 C10 . . 112.94(18) ?
O5 C11 H11A . . 109.0 ?
C10 C11 H11A . . 109.0 ?
O5 C11 H11B . . 109.0 ?
C10 C11 H11B . . 109.0 ?
H11A C11 H11B . . 107.8 ?
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 N1 . 1.230(2) ?
O2 N1 . 1.245(2) ?
O3 C7 . 1.218(3) ?
O4 C7 . 1.335(3) ?
O4 C8 . 1.461(2) ?
O5 C11 . 1.424(3) ?
O5 H5B . 0.83(3) ?
N1 C2 . 1.440(3) ?
N2 C3 . 1.342(3) ?
N2 C10 . 1.459(3) ?
N2 H2A . 0.84(3) ?
C1 C6 . 1.375(3) ?
C1 C2 . 1.391(3) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.430(3) ?
C3 C4 . 1.425(3) ?
C4 C5 . 1.368(3) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.414(3) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.482(3) ?
C8 C9 . 1.501(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C10 C11 . 1.526(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
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
N2 H2A O2 . 0.84(3) 1.99(3) 2.642(2) 134(2) yes
O5 H5B O3 4_666 0.83(3) 2.02(3) 2.851(2) 177(3) yes
C8 H8A O5 1_455 0.9700 2.5100 3.271(3) 135.00 yes
C10 H10A O5 4_566 0.97 2.54 3.267(3) 132.0 yes
C10 H10B O1 2_657 0.9700 2.4300 3.168(3) 133.00 yes
C11 H11A O2 4_565 0.97 2.59 3.403(3) 141.6 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 C1 C2 C3 . . . . 0.0(3) ?
C6 C1 C2 N1 . . . . 178.9(2) ?
O1 N1 C2 C1 . . . . -3.9(3) ?
O2 N1 C2 C1 . . . . 176.5(2) ?
O1 N1 C2 C3 . . . . 175.0(2) ?
O2 N1 C2 C3 . . . . -4.6(3) ?
C10 N2 C3 C4 . . . . -0.1(3) ?
C10 N2 C3 C2 . . . . -179.3(2) ?
C1 C2 C3 N2 . . . . -178.8(2) ?
N1 C2 C3 N2 . . . . 2.4(3) ?
C1 C2 C3 C4 . . . . 2.0(3) ?
N1 C2 C3 C4 . . . . -176.81(19) ?
N2 C3 C4 C5 . . . . 178.7(2) ?
C2 C3 C4 C5 . . . . -2.1(3) ?
C3 C4 C5 C6 . . . . 0.3(3) ?
C2 C1 C6 C5 . . . . -1.9(3) ?
C2 C1 C6 C7 . . . . 177.1(2) ?
C4 C5 C6 C1 . . . . 1.8(3) ?
C4 C5 C6 C7 . . . . -177.2(2) ?
C8 O4 C7 O3 . . . . -2.2(3) ?
C8 O4 C7 C6 . . . . 176.60(18) ?
C1 C6 C7 O3 . . . . 2.8(3) ?
C5 C6 C7 O3 . . . . -178.3(2) ?
C1 C6 C7 O4 . . . . -176.1(2) ?
C5 C6 C7 O4 . . . . 2.9(3) ?
C7 O4 C8 C9 . . . . 168.7(2) ?
C3 N2 C10 C11 . . . . -76.3(3) ?
N2 C10 C11 O5 . . . . -57.4(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744634
