#------------------------------------------------------------------------------
#$Date: 2022-09-14 19:38:48 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/41/2204101.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_2204101
loop_
_publ_author_name
'Yin, Caixia'
'Huo, Fangjun'
'Yang, Pin'
_publ_section_title
;
Methyl 2-[hydroxy(4-nitrophenyl)methyl]acrylate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica, Section E'
_journal_page_first              o1331
_journal_page_last               o1332
_journal_paper_doi               10.1107/S1600536804016605
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C11 H11 N O5'
_chemical_formula_moiety         'C11 H11 N O5'
_chemical_formula_sum            'C11 H11 N O5'
_chemical_formula_weight         237.21
_chemical_melting_point          345
_chemical_name_common
;
Methyl 2-[hydroxy(4-nitrophenyl)methyl]acrylate
;
_chemical_name_systematic
;
Methyl 2-[hydroxy(4-nitrophenyl)methyl]acrylate
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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                97.748(6)
_cell_angle_beta                 99.660(6)
_cell_angle_gamma                110.765(5)
_cell_formula_units_Z            2
_cell_length_a                   6.817(3)
_cell_length_b                   8.598(4)
_cell_length_c                   10.457(5)
_cell_measurement_reflns_used    2414
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.60
_cell_volume                     552.3(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SHELXTL (Bruker, 2000)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.902
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1930
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.180
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         1755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0427
_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)+(0.0555P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                1284
_reflns_number_total             1755
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            wn6264.cif
_cod_database_code               2204101
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
O2 0.2993(2) -0.10869(16) 0.40558(14) 0.0403(4) Uani d . 1 O
O5 0.2084(3) 0.6246(2) -0.13995(15) 0.0480(5) Uani d . 1 O
O1 0.4625(3) 0.25697(17) 0.41777(14) 0.0421(4) Uani d . 1 O
H1 0.5049 0.1898 0.4544 0.063 Uiso calc R 1 H
C6 0.3084(3) 0.3021(2) 0.20855(19) 0.0296(5) Uani d . 1 C
O3 -0.0631(2) -0.21228(17) 0.37123(15) 0.0451(5) Uani d . 1 O
N 0.2702(3) 0.6714(2) -0.01775(19) 0.0388(5) Uani d . 1 N
O4 0.3244(3) 0.81967(19) 0.04215(16) 0.0561(5) Uani d . 1 O
C8 0.3471(3) 0.5912(3) 0.1980(2) 0.0334(5) Uani d . 1 C
H8 0.3825 0.7056 0.2407 0.040 Uiso calc R 1 H
C9 0.2809(3) 0.5410(2) 0.0610(2) 0.0307(5) Uani d . 1 C
C10 0.2263(3) 0.3744(2) -0.0051(2) 0.0335(5) Uani d . 1 C
H10 0.1799 0.3427 -0.0991 0.040 Uiso calc R 1 H
C11 0.2413(3) 0.2554(2) 0.0698(2) 0.0319(5) Uani d . 1 C
H11 0.2057 0.1411 0.0265 0.038 Uiso calc R 1 H
C4 0.3281(3) 0.1693(2) 0.28782(19) 0.0326(5) Uani d . 1 C
H4 0.4016 0.1038 0.2425 0.049 Uiso calc R 1 H
C7 0.3606(3) 0.4705(2) 0.2718(2) 0.0319(5) Uani d . 1 C
H7 0.4056 0.5027 0.3658 0.027(5) Uiso calc R 1 H
C1 0.1273(4) -0.0976(2) 0.36468(19) 0.0315(5) Uani d . 1 C
C2 0.1094(3) 0.0427(2) 0.29850(18) 0.0299(5) Uani d . 1 C
C3 -0.0816(4) 0.0520(3) 0.2572(2) 0.0396(6) Uani d . 1 C
H3B -0.2089 -0.0310 0.2696 0.047 Uiso calc R 1 H
H3A -0.0902 0.1416 0.2155 0.047 Uiso calc R 1 H
C5 -0.0531(4) -0.3543(3) 0.4315(2) 0.0457(6) Uani d . 1 C
H5C 0.0359 -0.3101 0.5223 0.069 Uiso calc R 1 H
H5B 0.0105 -0.4185 0.3792 0.069 Uiso calc R 1 H
H5A -0.1991 -0.4292 0.4332 0.069 Uiso calc R 1 H
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
_geom_angle_publ_flag
O1 C4 C2 110.45(16) y
O1 C4 C6 108.33(15) y
O2 C1 O3 123.08(19) y
O2 C1 C2 122.91(19) y
O3 C1 C2 113.97(18) y
O4 N O5 123.69(18) ?
O4 N C9 118.45(17) ?
O5 N C9 117.86(18) ?
C1 O3 C5 115.72(16) y
C1 C2 C4 113.22(18) y
C3 C2 C1 121.05(19) y
C3 C2 C4 125.72(19) y
C6 C4 C2 113.30(16) y
C7 C6 C4 121.16(17) y
C7 C6 C11 119.35(19) ?
C8 C7 C6 120.55(18) ?
C8 C9 N 118.45(18) ?
C8 C9 C10 122.33(19) ?
C9 C8 C7 118.65(19) ?
C10 C11 C6 120.75(19) ?
C10 C9 N 119.21(18) ?
C11 C6 C4 119.47(17) y
C11 C10 C9 118.36(19) ?
C4 O1 H1 109.5 ?
C9 C8 H8 120.7 ?
C7 C8 H8 120.7 ?
C11 C10 H10 120.8 ?
C9 C10 H10 120.8 ?
C10 C11 H11 119.6 ?
C6 C11 H11 119.6 ?
O1 C4 H4 108.2 ?
C6 C4 H4 108.2 ?
C2 C4 H4 108.2 ?
C8 C7 H7 119.7 ?
C6 C7 H7 119.7 ?
C2 C3 H3B 120.0 ?
C2 C3 H3A 120.0 ?
H3B C3 H3A 120.0 ?
O3 C5 H5C 109.5 ?
O3 C5 H5B 109.5 ?
H5C C5 H5B 109.5 ?
O3 C5 H5A 109.5 ?
H5C C5 H5A 109.5 ?
H5B C5 H5A 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 1.439(2) y
O1 H1 0.8400 ?
O2 C1 1.220(2) y
O3 C1 1.343(2) y
O3 C5 1.464(2) y
O5 N 1.238(2) ?
N O4 1.236(2) ?
N C9 1.492(3) ?
C1 C2 1.499(3) y
C2 C3 1.335(3) y
C4 C2 1.536(3) y
C6 C4 1.528(3) y
C6 C7 1.399(3) ?
C6 C11 1.402(3) ?
C8 C9 1.386(3) ?
C8 C7 1.394(3) ?
C8 H8 0.9500 ?
C9 C10 1.392(3) ?
C10 C11 1.392(3) ?
C10 H10 0.9500 ?
C11 H11 0.9500 ?
C4 H4 1.0000 ?
C7 H7 0.9500 ?
C3 H3B 0.9500 ?
C3 H3A 0.9500 ?
C5 H5C 0.9800 ?
C5 H5B 0.9800 ?
C5 H5A 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
O1 H1 O2 . 0.84 2.38 2.916(2) 122 y
O1 H1 O2 2_656 0.84 2.17 2.961(2) 158 y
C8 H8 O2 1_565 0.95 2.46 3.286(3) 145 y
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
C7 C8 C9 C10 0.4(3)
C7 C8 C9 N -179.01(18)
O4 N C9 C8 1.3(3)
O5 N C9 C8 -179.16(18)
O4 N C9 C10 -178.18(18)
O5 N C9 C10 1.4(3)
C8 C9 C10 C11 -0.7(3)
N C9 C10 C11 178.78(18)
C9 C10 C11 C6 0.4(3)
C7 C6 C11 C10 0.0(3)
C4 C6 C11 C10 -178.63(19)
C7 C6 C4 O1 -17.2(3)
C11 C6 C4 O1 161.42(18)
C7 C6 C4 C2 105.7(2)
C11 C6 C4 C2 -75.7(2)
C9 C8 C7 C6 0.0(3)
C11 C6 C7 C8 -0.3(3)
C4 C6 C7 C8 178.38(19)
C5 O3 C1 O2 0.1(3)
C5 O3 C1 C2 178.18(17)
O2 C1 C2 C3 -178.79(18)
O3 C1 C2 C3 3.1(3)
O2 C1 C2 C4 0.0(3)
O3 C1 C2 C4 -178.10(15)
O1 C4 C2 C3 114.8(2)
C6 C4 C2 C3 -6.9(3)
O1 C4 C2 C1 -63.9(2)
C6 C4 C2 C1 174.35(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9543294
