#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/89/2228949.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_2228949
loop_
_publ_author_name
'Guo, Bing'
'Shi, Ya-Bin'
'Yao, Jin-Hua'
'Guan, Jian-Ning'
_publ_section_title
;
 Ethyl 2-(2-hydroxy-5-nitrophenyl)acetate
;
_journal_coeditor_code           BQ2266
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o509
_journal_paper_doi               10.1107/S1600536811000389
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H11 N O5'
_chemical_formula_moiety         'C10 H11 N O5'
_chemical_formula_sum            'C10 H11 N O5'
_chemical_formula_weight         225.20
_chemical_melting_point          423
_chemical_name_systematic
;
Ethyl 2-(2-hydroxy-5-nitrophenyl)acetate
;
_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                 97.85(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.066(2)
_cell_length_b                   10.860(2)
_cell_length_c                   8.6970(17)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1035.4(3)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1989)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0555
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3894
_diffrn_reflns_theta_full        25.37
_diffrn_reflns_theta_max         25.37
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.9884
_exptl_absorpt_correction_T_min  0.9656
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.187
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0566
_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)+(0.0990P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1534
_reflns_number_gt                1382
_reflns_number_total             1905
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            bq2266.cif
_cod_data_source_block           I
_cod_original_cell_volume        1035.4(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2228949
_cod_database_fobs_code          2228949
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
N N 0.44757(17) 0.77034(17) -0.2435(2) 0.0459(5) Uani d . 1 . .
O O1 0.84749(14) 0.35380(12) 0.03010(16) 0.0410(4) Uani d . 1 . .
C C1 0.9150(3) 0.1519(2) -0.0185(3) 0.0683(9) Uani d . 1 . .
H H1A 0.9544 0.1015 -0.0874 0.102 Uiso calc R 1 . .
H H1B 0.8344 0.1209 -0.0133 0.102 Uiso calc R 1 . .
H H1C 0.9614 0.1503 0.0832 0.102 Uiso calc R 1 . .
O O2 0.86074(14) 0.51755(12) -0.11869(19) 0.0463(4) Uani d . 1 . .
C C2 0.9070(2) 0.2789(2) -0.0764(3) 0.0514(6) Uani d . 1 . .
H H2A 0.9880 0.3106 -0.0830 0.062 Uiso calc R 1 . .
H H2B 0.8604 0.2813 -0.1792 0.062 Uiso calc R 1 . .
O O3 0.83631(14) 0.75835(12) 0.23336(18) 0.0447(4) Uani d . 1 . .
H H3A 0.8435 0.8252 0.2774 0.067 Uiso calc R 1 . .
C C3 0.82574(18) 0.46958(16) -0.0074(2) 0.0328(5) Uani d . 1 . .
O O4 0.40609(16) 0.67242(16) -0.2982(2) 0.0621(5) Uani d . 1 . .
C C4 0.7546(2) 0.53250(18) 0.1045(2) 0.0428(6) Uani d . 1 . .
H H4A 0.6900 0.4778 0.1272 0.051 Uiso calc R 1 . .
H H4B 0.8082 0.5467 0.2008 0.051 Uiso calc R 1 . .
C C5 0.69929(19) 0.65258(17) 0.0481(2) 0.0344(5) Uani d . 1 . .
O O5 0.40459(18) 0.86915(17) -0.2870(2) 0.0748(7) Uani d . 1 . .
C C6 0.60137(19) 0.65579(17) -0.0694(2) 0.0357(5) Uani d . 1 . .
H H6A 0.5693 0.5828 -0.1137 0.043 Uiso calc R 1 . .
C C7 0.55121(18) 0.76775(18) -0.1209(2) 0.0360(5) Uani d . 1 . .
C C8 0.5979(2) 0.87793(19) -0.0587(3) 0.0396(5) Uani d . 1 . .
H H8A 0.5650 0.9525 -0.0968 0.048 Uiso calc R 1 . .
C C9 0.6931(2) 0.87561(18) 0.0595(2) 0.0391(5) Uani d . 1 . .
H H9A 0.7243 0.9491 0.1032 0.047 Uiso calc R 1 . .
C C10 0.74381(18) 0.76365(17) 0.1149(2) 0.0332(5) 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'
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
O5 N O4 . . 122.4(2) ?
O5 N C7 . . 118.79(18) ?
O4 N C7 . . 118.85(17) ?
C3 O1 C2 . . 117.42(16) ?
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 ?
O1 C2 C1 . . 108.58(19) ?
O1 C2 H2A . . 110.0 ?
C1 C2 H2A . . 110.0 ?
O1 C2 H2B . . 110.0 ?
C1 C2 H2B . . 110.0 ?
H2A C2 H2B . . 108.4 ?
C10 O3 H3A . . 109.5 ?
O2 C3 O1 . . 122.96(19) ?
O2 C3 C4 . . 125.33(17) ?
O1 C3 C4 . . 111.71(17) ?
C5 C4 C3 . . 114.36(17) ?
C5 C4 H4A . . 108.7 ?
C3 C4 H4A . . 108.7 ?
C5 C4 H4B . . 108.7 ?
C3 C4 H4B . . 108.7 ?
H4A C4 H4B . . 107.6 ?
C6 C5 C10 . . 118.72(17) ?
C6 C5 C4 . . 120.57(18) ?
C10 C5 C4 . . 120.70(19) ?
C5 C6 C7 . . 119.96(18) ?
C5 C6 H6A . . 120.0 ?
C7 C6 H6A . . 120.0 ?
C8 C7 C6 . . 121.4(2) ?
C8 C7 N . . 118.96(18) ?
C6 C7 N . . 119.64(18) ?
C9 C8 C7 . . 119.06(18) ?
C9 C8 H8A . . 120.5 ?
C7 C8 H8A . . 120.5 ?
C8 C9 C10 . . 120.47(18) ?
C8 C9 H9A . . 119.8 ?
C10 C9 H9A . . 119.8 ?
O3 C10 C9 . . 121.81(18) ?
O3 C10 C5 . . 117.85(17) ?
C9 C10 C5 . . 120.34(19) ?
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
N O5 . 1.213(2) ?
N O4 . 1.228(2) ?
N C7 . 1.455(3) ?
O1 C3 . 1.313(2) ?
O1 C2 . 1.456(2) ?
C1 C2 . 1.466(3) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
O2 C3 . 1.208(2) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
O3 C10 . 1.351(3) ?
O3 H3A . 0.8200 ?
C3 C4 . 1.498(3) ?
C4 C5 . 1.495(3) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 C6 . 1.385(3) ?
C5 C10 . 1.399(3) ?
C6 C7 . 1.385(3) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.384(3) ?
C8 C9 . 1.369(3) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.397(3) ?
C9 H9A . 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
O3 H3A O2 4_576 0.82 1.93 2.749(2) 180 yes
C2 H2A O3 3_765 0.97 2.60 3.340(3) 134 yes
C4 H4A O4 3_665 0.97 2.54 3.431(3) 153 yes
C6 H6A O5 2_644 0.93 2.51 3.351(3) 151 yes
C8 H8A O4 2_654 0.93 2.59 3.430(3) 150 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
C3 O1 C2 C1 . . . . -176.2(2) ?
C2 O1 C3 O2 . . . . -5.6(3) ?
C2 O1 C3 C4 . . . . 174.94(19) ?
O2 C3 C4 C5 . . . . 15.6(3) ?
O1 C3 C4 C5 . . . . -164.98(18) ?
C3 C4 C5 C6 . . . . 71.4(3) ?
C3 C4 C5 C10 . . . . -109.9(2) ?
C10 C5 C6 C7 . . . . 1.4(3) ?
C4 C5 C6 C7 . . . . -179.79(18) ?
C5 C6 C7 C8 . . . . 0.9(3) ?
C5 C6 C7 N . . . . -179.43(17) ?
O5 N C7 C8 . . . . -0.4(3) ?
O4 N C7 C8 . . . . -179.8(2) ?
O5 N C7 C6 . . . . 179.8(2) ?
O4 N C7 C6 . . . . 0.5(3) ?
C6 C7 C8 C9 . . . . -2.1(3) ?
N C7 C8 C9 . . . . 178.19(18) ?
C7 C8 C9 C10 . . . . 1.0(3) ?
C8 C9 C10 O3 . . . . -178.73(19) ?
C8 C9 C10 C5 . . . . 1.3(3) ?
C6 C5 C10 O3 . . . . 177.52(17) ?
C4 C5 C10 O3 . . . . -1.3(3) ?
C6 C5 C10 C9 . . . . -2.5(3) ?
C4 C5 C10 C9 . . . . 178.75(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8438545
