#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/71/2207197.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_2207197
loop_
_publ_author_name
'Chun-Nian Xia'
'Wei-Xiao Hu'
'Wei Zhou'
_publ_section_title
;
 2-Methyl-2-nitropropyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
;
_journal_coeditor_code           CV6584
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3757
_journal_page_last               o3758
_journal_paper_doi               10.1107/S1600536805033192
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H15 N O6'
_chemical_formula_moiety         'C13 H15 N O6'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.26
_chemical_melting_point          .417E-305
_chemical_name_systematic
;
2-Methyl-2-nitropropyl 3-(3,4-dihydroxyphenyl)prop-2-enoate
;
_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           SHELXL97
_cell_angle_alpha                90.000
_cell_angle_beta                 100.73(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.739(4)
_cell_length_b                   10.7660(17)
_cell_length_c                   22.112(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      12.63
_cell_measurement_theta_min      10.16
_cell_volume                     1342.3(10)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4, PSI and EAC (Enraf--Nonius, 1994)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1999)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2960
_diffrn_reflns_theta_full        25.17
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0.3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            'light brown'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.149
_refine_ls_extinction_coef       0.0107(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2406
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0428
_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)+(0.0573P)²+0.3869P] where P=  (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1347
_reflns_number_gt                1319
_reflns_number_total             2406
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6584.cif
_cod_data_source_block           I
_cod_original_cell_volume        1342.3(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2207197
_cod_database_fobs_code          2207197
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_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
O1 0.3313(4) -1.37014(19) -0.00007(10) 0.0785(7) Uani d D 1 O
H1X 0.236(5) -1.348(3) 0.0213(14) 0.109(12) Uiso d D 1 H
O2 0.7019(4) -1.4027(2) -0.05916(12) 0.0854(7) Uani d D 1 O
H2X 0.668(6) -1.450(3) -0.0331(12) 0.089(12) Uiso d D 1 H
O3 -0.0262(4) -0.7172(2) -0.07424(9) 0.0908(8) Uani d . 1 O
O4 0.1810(3) -0.64476(16) -0.14333(8) 0.0622(5) Uani d . 1 O
O5 -0.0245(5) -0.6416(3) -0.29729(11) 0.1135(10) Uani d . 1 O
O6 0.1490(4) -0.4713(3) -0.26910(12) 0.1111(9) Uani d . 1 O
N1 0.0086(4) -0.5529(3) -0.26387(11) 0.0675(7) Uani d . 1 N
C1 0.3612(4) -1.0617(2) -0.07067(10) 0.0478(6) Uani d . 1 C
C2 0.2869(4) -1.1586(2) -0.03775(11) 0.0525(7) Uani d . 1 C
H2 0.1584 -1.1463 -0.0183 0.063 Uiso calc R 1 H
C3 0.3964(5) -1.2717(2) -0.03298(11) 0.0528(7) Uani d . 1 C
C4 0.5887(5) -1.2915(2) -0.06213(12) 0.0561(7) Uani d . 1 C
C5 0.6654(5) -1.1961(2) -0.09488(12) 0.0589(7) Uani d . 1 C
H5 0.7936 -1.2091 -0.1144 0.071 Uiso calc R 1 H
C6 0.5563(4) -1.0823(2) -0.09926(11) 0.0528(7) Uani d . 1 C
H6 0.6118 -1.0186 -0.1212 0.063 Uiso calc R 1 H
C7 0.2349(4) -0.9431(2) -0.07435(11) 0.0548(7) Uani d . 1 C
H7 0.1085 -0.9395 -0.0535 0.066 Uiso calc R 1 H
C8 0.2762(5) -0.8409(2) -0.10323(11) 0.0567(7) Uani d . 1 C
H8 0.4038 -0.8387 -0.1237 0.068 Uiso calc R 1 H
C9 0.1276(5) -0.7312(3) -0.10401(11) 0.0605(7) Uani d . 1 C
C10 0.0405(5) -0.5326(2) -0.15310(13) 0.0619(7) Uani d . 1 C
H10A 0.1439 -0.4618 -0.1545 0.074 Uiso calc R 1 H
H10B -0.0421 -0.5207 -0.1191 0.074 Uiso calc R 1 H
C11 -0.1374(4) -0.5402(2) -0.21257(11) 0.0498(6) Uani d . 1 C
C12 -0.2713(5) -0.4182(2) -0.22434(13) 0.0669(8) Uani d . 1 C
H12A -0.3713 -0.4204 -0.2643 0.100 Uiso calc R 1 H
H12B -0.1602 -0.3511 -0.2226 0.100 Uiso calc R 1 H
H12C -0.3669 -0.4061 -0.1935 0.100 Uiso calc R 1 H
C13 -0.3040(5) -0.6492(3) -0.21551(15) 0.0779(9) Uani d . 1 C
H13A -0.2140 -0.7248 -0.2100 0.117 Uiso calc R 1 H
H13B -0.4082 -0.6505 -0.2549 0.117 Uiso calc R 1 H
H13C -0.3958 -0.6417 -0.1836 0.117 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
C3 O1 H1X 111(2) ?
C4 O2 H2X 114(2) ?
C9 O4 C10 119.1(2) yes
O5 N1 O6 123.3(3) yes
O5 N1 C11 118.6(3) yes
O6 N1 C11 118.0(3) yes
C2 C1 C6 117.9(2) ?
C2 C1 C7 119.3(2) ?
C6 C1 C7 122.8(2) ?
C3 C2 C1 122.0(2) ?
C3 C2 H2 119.0 ?
C1 C2 H2 119.0 ?
C2 C3 O1 124.1(2) ?
C2 C3 C4 119.6(2) ?
O1 C3 C4 116.3(2) yes
O2 C4 C5 119.1(2) yes
O2 C4 C3 121.7(2) ?
C5 C4 C3 119.2(2) ?
C6 C5 C4 121.1(2) ?
C6 C5 H5 119.4 ?
C4 C5 H5 119.4 ?
C5 C6 C1 120.1(2) ?
C5 C6 H6 119.9 ?
C1 C6 H6 119.9 ?
C8 C7 C1 128.7(2) ?
C8 C7 H7 115.7 ?
C1 C7 H7 115.7 ?
C7 C8 C9 121.8(2) ?
C7 C8 H8 119.1 ?
C9 C8 H8 119.1 ?
O3 C9 O4 123.0(2) yes
O3 C9 C8 125.6(2) ?
O4 C9 C8 111.4(2) ?
O4 C10 C11 110.7(2) yes
O4 C10 H10A 109.5 ?
C11 C10 H10A 109.5 ?
O4 C10 H10B 109.5 ?
C11 C10 H10B 109.5 ?
H10A C10 H10B 108.1 ?
C13 C11 C10 113.6(2) ?
C13 C11 C12 111.7(2) ?
C10 C11 C12 109.9(2) ?
C13 C11 N1 109.1(2) ?
C10 C11 N1 105.9(2) ?
C12 C11 N1 106.1(2) ?
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 ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.376(3) yes
O1 H1X 0.822(18) ?
O2 C4 1.358(3) yes
O2 H2X 0.821(18) ?
O3 C9 1.205(3) yes
O4 C9 1.347(3) yes
O4 C10 1.445(3) yes
O5 N1 1.201(3) yes
O6 N1 1.212(3) yes
N1 C11 1.537(3) yes
C1 C2 1.384(3) ?
C1 C6 1.402(3) ?
C1 C7 1.463(3) ?
C2 C3 1.366(3) ?
C2 H2 0.9300 ?
C3 C4 1.394(3) ?
C4 C5 1.375(3) ?
C5 C6 1.372(3) ?
C5 H5 0.9300 ?
C6 H6 0.9300 ?
C7 C8 1.316(3) yes
C7 H7 0.9300 ?
C8 C9 1.455(3) ?
C8 H8 0.9300 ?
C10 C11 1.510(4) ?
C10 H10A 0.9700 ?
C10 H10B 0.9700 ?
C11 C13 1.507(4) ?
C11 C12 1.519(3) ?
C12 H12A 0.9599 ?
C12 H12B 0.9599 ?
C12 H12C 0.9599 ?
C13 H13A 0.9599 ?
C13 H13B 0.9599 ?
C13 H13C 0.9599 ?
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 H1X O3 3_535 0.822(18) 1.958(19) 2.779(3) 175(4) yes
C10 H10B O2 1_465 0.97 2.50 3.399(3) 154 yes
C12 H12B O5 2_554 0.96 2.50 3.417(4) 161 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
C6 C1 C2 C3 -0.4(4)
C7 C1 C2 C3 179.6(2)
C1 C2 C3 O1 179.0(2)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 O2 -179.4(3)
O1 C3 C4 O2 1.3(4)
C2 C3 C4 C5 0.4(4)
O1 C3 C4 C5 -178.9(2)
O2 C4 C5 C6 179.9(3)
C3 C4 C5 C6 0.0(4)
C4 C5 C6 C1 -0.7(4)
C2 C1 C6 C5 0.9(4)
C7 C1 C6 C5 -179.1(2)
C2 C1 C7 C8 -179.7(3)
C6 C1 C7 C8 0.3(4)
C1 C7 C8 C9 177.9(2)
C10 O4 C9 O3 -3.4(4)
C10 O4 C9 C8 176.0(2)
C7 C8 C9 O3 8.4(5)
C7 C8 C9 O4 -171.0(3)
C9 O4 C10 C11 -100.9(3)
O4 C10 C11 C13 58.1(3)
O4 C10 C11 C12 -176.0(2)
O4 C10 C11 N1 -61.7(3)
O5 N1 C11 C13 -0.3(3)
O6 N1 C11 C13 178.5(3)
O5 N1 C11 C10 122.3(3)
O6 N1 C11 C10 -58.8(3)
O5 N1 C11 C12 -120.8(3)
O6 N1 C11 C12 58.0(3)
