#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/48/2224839.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_2224839
loop_
_publ_author_name
'Yang, Hongxiang'
_publ_section_title
;
 4-Hydroxy-3-nitrophenyl pentanoate
;
_journal_coeditor_code           BG2323
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o481
_journal_paper_doi               10.1107/S1600536810002795
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C11 H13 N O5'
_chemical_formula_moiety         'C11 H13 N O5'
_chemical_formula_sum            'C11 H13 N O5'
_chemical_formula_weight         239.22
_chemical_melting_point          310
_chemical_name_common            '4-Hydroxy-3-nitrophenyl pentanoate'
_chemical_name_systematic
;
4-Hydroxy-3-nitrophenyl pentanoate
;
_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
_cell_angle_alpha                67.340(12)
_cell_angle_beta                 81.074(17)
_cell_angle_gamma                77.114(16)
_cell_formula_units_Z            2
_cell_length_a                   5.3006(14)
_cell_length_b                   10.435(2)
_cell_length_c                   11.365(3)
_cell_measurement_reflns_used    1965
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      2.1
_cell_volume                     563.8(2)
_computing_cell_refinement       'CrystalClear (Rigaku/MSC, 2007)'
_computing_data_collection       'CrystalClear (Rigaku/MSC, 2007)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ 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  0.0230
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5175
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  0.9933
_exptl_absorpt_correction_T_min  0.9801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.266
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1003
_reflns_number_gt                1972
_reflns_number_total             2639
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bg2323.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2224839
_cod_database_fobs_code          2224839
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 0.44132(16) 0.16466(9) 1.06926(8) 0.0260(2) Uani d . 1 . .
O O2 0.57276(18) 0.35065(8) 1.06023(9) 0.0294(2) Uani d . 1 . .
O O3 0.97659(17) 0.43498(8) 0.91208(9) 0.0266(2) Uani d . 1 . .
H H3 0.849(3) 0.4414(15) 0.9691(14) 0.040 Uiso d . 1 . .
O O4 1.05538(15) -0.03140(8) 0.78112(8) 0.0208(2) Uani d . 1 . .
O O5 0.75270(16) 0.06969(8) 0.63771(8) 0.0238(2) Uani d . 1 . .
N N1 0.59085(19) 0.24914(10) 1.02548(9) 0.0206(2) Uani d . 1 . .
C C1 0.8163(2) 0.11536(11) 0.89438(11) 0.0183(3) Uani d . 1 . .
H H1 0.6925 0.0544 0.9283 0.022 Uiso calc R 1 . .
C C2 0.7982(2) 0.23078(11) 0.93060(10) 0.0175(3) Uani d . 1 . .
C C3 0.9768(2) 0.32268(11) 0.88102(11) 0.0194(3) Uani d . 1 . .
C C4 1.1752(2) 0.29541(12) 0.79260(11) 0.0218(3) Uani d . 1 . .
H H4 1.2982 0.3567 0.7566 0.026 Uiso calc R 1 . .
C C5 1.1953(2) 0.18137(12) 0.75690(11) 0.0209(3) Uani d . 1 . .
H H5 1.3315 0.1641 0.6969 0.025 Uiso calc R 1 . .
C C6 1.0158(2) 0.09177(11) 0.80900(11) 0.0181(3) Uani d . 1 . .
C C7 0.9099(2) -0.03100(12) 0.69151(10) 0.0178(3) Uani d . 1 . .
C C8 0.9818(2) -0.16744(12) 0.66970(11) 0.0197(3) Uani d . 1 . .
H H8A 1.0362 -0.2441 0.7506 0.024 Uiso calc R 1 . .
H H8B 1.1326 -0.1620 0.6056 0.024 Uiso calc R 1 . .
C C9 0.7641(2) -0.20491(11) 0.62381(11) 0.0210(3) Uani d . 1 . .
H H9A 0.6992 -0.1255 0.5467 0.025 Uiso calc R 1 . .
H H9B 0.6189 -0.2196 0.6911 0.025 Uiso calc R 1 . .
C C10 0.8556(2) -0.33818(12) 0.59220(12) 0.0238(3) Uani d . 1 . .
H H10A 0.9660 -0.3154 0.5108 0.029 Uiso calc R 1 . .
H H10B 0.9636 -0.4093 0.6601 0.029 Uiso calc R 1 . .
C C11 0.6337(3) -0.40135(13) 0.58021(14) 0.0332(3) Uani d . 1 . .
H H11A 0.5280 -0.4282 0.6618 0.050 Uiso calc R 1 . .
H H11B 0.7039 -0.4851 0.5581 0.050 Uiso calc R 1 . .
H H11C 0.5260 -0.3316 0.5130 0.050 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 O3 H3 . . 109.7(10) ?
C7 O4 C6 . . 117.46(9) ?
O1 N1 O2 . . 122.30(9) ?
O1 N1 C2 . . 119.42(9) ?
O2 N1 C2 . . 118.27(9) ?
C6 C1 C2 . . 118.66(10) ?
C6 C1 H1 . . 120.7 ?
C2 C1 H1 . . 120.7 ?
C1 C2 C3 . . 121.70(9) ?
C1 C2 N1 . . 117.19(10) ?
C3 C2 N1 . . 121.08(10) ?
O3 C3 C4 . . 116.78(10) ?
O3 C3 C2 . . 125.67(10) ?
C4 C3 C2 . . 117.55(10) ?
C5 C4 C3 . . 121.13(11) ?
C5 C4 H4 . . 119.4 ?
C3 C4 H4 . . 119.4 ?
C4 C5 C6 . . 119.68(10) ?
C4 C5 H5 . . 120.2 ?
C6 C5 H5 . . 120.2 ?
C1 C6 C5 . . 121.27(10) ?
C1 C6 O4 . . 119.95(10) ?
C5 C6 O4 . . 118.54(9) ?
O5 C7 O4 . . 122.35(10) ?
O5 C7 C8 . . 126.85(12) ?
O4 C7 C8 . . 110.77(10) ?
C7 C8 C9 . . 113.82(9) ?
C7 C8 H8A . . 108.8 ?
C9 C8 H8A . . 108.8 ?
C7 C8 H8B . . 108.8 ?
C9 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
C8 C9 C10 . . 111.43(9) ?
C8 C9 H9A . . 109.3 ?
C10 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
C10 C9 H9B . . 109.3 ?
H9A C9 H9B . . 108.0 ?
C11 C10 C9 . . 113.11(10) ?
C11 C10 H10A . . 109.0 ?
C9 C10 H10A . . 109.0 ?
C11 C10 H10B . . 109.0 ?
C9 C10 H10B . . 109.0 ?
H10A C10 H10B . . 107.8 ?
C10 C11 H11A . . 109.5 ?
C10 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C10 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 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 N1 . 1.2264(12) ?
O2 N1 . 1.2461(12) ?
O3 C3 . 1.3476(13) ?
O3 H3 . 0.872(14) ?
O4 C7 . 1.3678(15) ?
O4 C6 . 1.4032(12) ?
O5 C7 . 1.2019(14) ?
N1 C2 . 1.4508(14) ?
C1 C6 . 1.3675(15) ?
C1 C2 . 1.3956(15) ?
C1 H1 . 0.9500 ?
C2 C3 . 1.3987(16) ?
C3 C4 . 1.3984(16) ?
C4 C5 . 1.3762(16) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3878(16) ?
C5 H5 . 0.9500 ?
C7 C8 . 1.4948(15) ?
C8 C9 . 1.5171(16) ?
C8 H8A . 0.9900 ?
C8 H8B . 0.9900 ?
C9 C10 . 1.5258(14) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
C10 C11 . 1.5170(18) ?
C10 H10A . 0.9900 ?
C10 H10B . 0.9900 ?
C11 H11A . 0.9800 ?
C11 H11B . 0.9800 ?
C11 H11C . 0.9800 ?
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 H3 O2 . 0.872(14) 1.871(14) 2.6022(13) 140.2(13) 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 . . . . 0.58(18) ?
C6 C1 C2 N1 . . . . -177.40(10) ?
O1 N1 C2 C1 . . . . -0.25(16) ?
O2 N1 C2 C1 . . . . 179.25(11) ?
O1 N1 C2 C3 . . . . -178.24(11) ?
O2 N1 C2 C3 . . . . 1.26(17) ?
C1 C2 C3 O3 . . . . -178.86(12) ?
N1 C2 C3 O3 . . . . -0.96(19) ?
C1 C2 C3 C4 . . . . 0.34(18) ?
N1 C2 C3 C4 . . . . 178.24(11) ?
O3 C3 C4 C5 . . . . 178.56(11) ?
C2 C3 C4 C5 . . . . -0.72(18) ?
C3 C4 C5 C6 . . . . 0.17(19) ?
C2 C1 C6 C5 . . . . -1.16(18) ?
C2 C1 C6 O4 . . . . 173.22(10) ?
C4 C5 C6 C1 . . . . 0.80(19) ?
C4 C5 C6 O4 . . . . -173.66(11) ?
C7 O4 C6 C1 . . . . 83.13(13) ?
C7 O4 C6 C5 . . . . -102.34(13) ?
C6 O4 C7 O5 . . . . -0.14(15) ?
C6 O4 C7 C8 . . . . 177.99(8) ?
O5 C7 C8 C9 . . . . -28.67(16) ?
O4 C7 C8 C9 . . . . 153.30(9) ?
C7 C8 C9 C10 . . . . 175.07(9) ?
C8 C9 C10 C11 . . . . 164.72(10) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744364
