#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2203365.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2203365
loop_
_publ_author_name
'Huo, Fangjun'
'Yin, Caixia'
'Guo, Wei'
'Xia, Chizhong'
'Yang, Pin'
_publ_section_title
;
The Baylis--Hillman adduct of 4-nitrobenzaldehyde and cyclohex-2-en-1-one:
2-[hydroxy(4-nitrophenyl)methyl]-cyclohex-2-en-1-one
;
_journal_issue                 3
_journal_name_full             'Acta Crystallographica, Section E'
_journal_page_first            o419
_journal_page_last             o421
_journal_volume                60
_journal_year                  2004
_chemical_formula_iupac        'C13 H13 N O4'
_chemical_formula_moiety       'C13 H13 N O4'
_chemical_formula_sum          'C13 H13 N O4'
_chemical_formula_weight       247.24
_chemical_melting_point        362
_chemical_name_common
2-[hydroxy(4-nitrophenyl)methyl]-cyclohex-2-en-1-one
_chemical_name_systematic
;
2-[hydroxy(4-nitrophenyl)methyl]-cyclohex-2-en-1-one
;
_symmetry_cell_setting         Monoclinic
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 21/n'
_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               97.884(4)
_cell_angle_gamma              90.00
_cell_formula_units_Z          4
_cell_length_a                 6.7202(16)
_cell_length_b                 10.131(3)
_cell_length_c                 17.813(4)
_cell_measurement_reflns_used  6932
_cell_measurement_temperature  298(2)
_cell_measurement_theta_max    22.2
_cell_measurement_theta_min    2.32
_cell_volume                   1201.2(5)
_computing_cell_refinement     'SAINT (Bruker, 2000)'
_computing_data_collection     'SMART (Bruker, 2000)'
_computing_data_reduction      SAINT
_computing_molecular_graphics  'SHELXTL (Bruker, 1999)'
_computing_publication_material SHELXTL
_computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution  'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature    298(2)
_diffrn_detector_area_resol_mean '100x100 microns'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type 'Bruker SMART 1K CCD area-detector'
_diffrn_measurement_method     \w
_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 0.087
_diffrn_reflns_av_sigmaI/netI  0.073
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_l_max     21
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_number          5777
_diffrn_reflns_theta_full      25.0
_diffrn_reflns_theta_max       25.0
_diffrn_reflns_theta_min       2.3
_diffrn_standards_decay_%      0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time 0
_diffrn_standards_number       0
_exptl_absorpt_coefficient_mu  0.10
_exptl_absorpt_correction_T_max 0.99
_exptl_absorpt_correction_T_min 0.98
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour          colorless
_exptl_crystal_density_diffrn  1.367
_exptl_crystal_density_meas    ?
_exptl_crystal_density_method  'not measured'
_exptl_crystal_description     pillar
_exptl_crystal_F_000           520
_exptl_crystal_size_max        0.20
_exptl_crystal_size_mid        0.20
_exptl_crystal_size_min        0.10
_refine_diff_density_max       0.21
_refine_diff_density_min       -0.17
_refine_ls_extinction_coef     ?
_refine_ls_extinction_method   none
_refine_ls_goodness_of_fit_ref 1.01
_refine_ls_hydrogen_treatment  constr
_refine_ls_matrix_type         full
_refine_ls_number_parameters   164
_refine_ls_number_reflns       2102
_refine_ls_number_restraints   0
_refine_ls_restrained_S_all    1.01
_refine_ls_R_factor_all        0.085
_refine_ls_R_factor_gt         0.056
_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/[\s^2^(Fo^2^)+(0.0649P)^2^] where P = (Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme    calc
_refine_ls_wR_factor_gt        0.131
_refine_ls_wR_factor_ref       0.146
_reflns_number_gt              1396
_reflns_number_total           2102
_reflns_threshold_expression   I>2\s(I)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
N 1.2210(4) 0.9545(2) 0.89306(12) 0.0458(6) Uani d . 1 . . N
C11 1.0828(4) 0.8466(2) 0.86600(13) 0.0374(6) Uani d . 1 . . C
C7 0.6730(3) 0.5416(2) 0.78101(13) 0.0385(6) Uani d . 1 . . C
H7 0.7300 0.4928 0.7415 0.046 Uiso calc R 1 . . H
C2 0.6266(4) 0.4443(2) 0.84077(13) 0.0373(6) Uani d . 1 . . C
O1 0.9278(3) 0.33254(17) 0.83014(12) 0.0579(6) Uani d . 1 . . O
C9 1.0070(4) 0.6590(2) 0.78803(13) 0.0398(6) Uani d . 1 . . C
H9 1.0425 0.5991 0.7526 0.048 Uiso calc R 1 . . H
C8 0.8248(4) 0.6466(2) 0.81357(12) 0.0346(6) Uani d . 1 . . C
O2 0.4904(2) 0.59957(17) 0.74825(9) 0.0457(5) Uani d . 1 . . O
H2 0.5141 0.6617 0.7213 0.069 Uiso calc R 1 . . H
O4 1.3845(3) 0.95851(18) 0.87022(12) 0.0649(6) Uani d . 1 . . O
C12 0.9003(4) 0.8371(2) 0.89301(13) 0.0409(6) Uani d . 1 . . C
H12 0.8645 0.8972 0.9283 0.049 Uiso calc R 1 . . H
O3 1.1677(3) 1.03383(19) 0.93766(12) 0.0676(6) Uani d . 1 . . O
C1 0.7776(4) 0.3396(2) 0.86083(14) 0.0444(7) Uani d . 1 . . C
C13 0.7733(4) 0.7365(2) 0.86636(13) 0.0422(6) Uani d . 1 . . C
H13 0.6500 0.7284 0.8841 0.051 Uiso calc R 1 . . H
C10 1.1405(4) 0.7596(2) 0.81411(14) 0.0421(6) Uani d . 1 . . C
H10 1.2645 0.7674 0.7969 0.050 Uiso calc R 1 . . H
C3 0.4580(4) 0.4432(2) 0.87028(15) 0.0484(7) Uani d . 1 . . C
H3 0.3625 0.5069 0.8535 0.058 Uiso calc R 1 . . H
C6 0.7267(5) 0.2352(3) 0.91566(18) 0.0675(9) Uani d . 1 . . C
H6A 0.6665 0.1605 0.8870 0.081 Uiso calc R 1 . . H
H6B 0.8502 0.2049 0.9453 0.081 Uiso calc R 1 . . H
C5 0.5855(4) 0.2813(3) 0.96908(17) 0.0693(9) Uani d . 1 . . C
H5A 0.5427 0.2060 0.9965 0.083 Uiso calc R 1 . . H
H5B 0.6559 0.3417 1.0058 0.083 Uiso calc R 1 . . H
C4 0.4077(5) 0.3478(3) 0.92858(17) 0.0643(9) Uani d . 1 . . C
H4A 0.3387 0.3944 0.9650 0.077 Uiso calc R 1 . . H
H4B 0.3164 0.2817 0.9042 0.077 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N 0.0495(15) 0.0395(13) 0.0465(14) -0.0033(11) -0.0002(11) 0.0062(11)
C11 0.0472(16) 0.0294(13) 0.0337(14) -0.0002(11) -0.0010(11) 0.0044(10)
C7 0.0430(15) 0.0355(14) 0.0366(14) 0.0042(11) 0.0036(11) -0.0046(11)
C2 0.0427(15) 0.0286(13) 0.0392(14) 0.0006(11) 0.0008(11) -0.0045(10)
O1 0.0491(12) 0.0497(12) 0.0749(14) 0.0103(9) 0.0084(10) -0.0035(9)
C9 0.0436(15) 0.0384(14) 0.0380(14) 0.0061(11) 0.0075(12) -0.0063(11)
C8 0.0410(15) 0.0320(13) 0.0303(13) 0.0045(11) 0.0032(11) 0.0029(10)
O2 0.0447(11) 0.0437(11) 0.0468(11) -0.0008(8) -0.0011(8) 0.0106(8)
O4 0.0562(13) 0.0568(13) 0.0820(15) -0.0115(11) 0.0104(11) 0.0003(11)
C12 0.0473(16) 0.0391(15) 0.0365(14) 0.0033(12) 0.0071(12) -0.0067(11)
O3 0.0806(15) 0.0513(12) 0.0721(14) -0.0124(10) 0.0154(12) -0.0243(11)
C1 0.0494(17) 0.0349(15) 0.0461(16) 0.0001(13) -0.0034(13) -0.0070(12)
C13 0.0470(16) 0.0403(15) 0.0423(15) -0.0044(12) 0.0170(12) -0.0047(12)
C10 0.0381(15) 0.0445(15) 0.0444(15) 0.0036(12) 0.0084(12) 0.0006(12)
C3 0.0497(17) 0.0401(15) 0.0548(17) 0.0076(13) 0.0054(13) 0.0108(12)
C6 0.085(2) 0.0451(17) 0.070(2) 0.0147(16) 0.0016(18) 0.0145(15)
C5 0.078(2) 0.065(2) 0.065(2) 0.0060(17) 0.0082(17) 0.0259(16)
C4 0.071(2) 0.0562(19) 0.069(2) 0.0009(15) 0.0189(16) 0.0213(15)
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
O1 C1 C2 . . 121.3(2) y
O1 C1 C6 . . 121.7(2) y
C2 C1 C6 . . 116.8(2) y
C1 C2 C3 . . 119.9(2) y
C1 C2 C7 . . 115.9(2) y
C3 C2 C7 . . 124.0(2) y
C2 C3 C4 . . 125.1(2) y
C3 C4 C5 . . 113.1(2) y
C4 C5 C6 . . 111.8(2) y
C1 C6 C5 . . 114.2(2) y
O2 C7 C2 . . 108.08(19) y
O2 C7 C8 . . 111.29(18) y
C2 C7 C8 . . 112.12(19) y
C7 C8 C9 . . 121.1(2) y
O3 N C11 . . 118.3(2) ?
O3 N O4 . . 123.5(2) ?
O4 N C11 . . 118.1(2) ?
C8 C9 C10 . . 121.3(2) ?
C9 C8 C13 . . 118.9(2) ?
C10 C11 C12 . . 122.5(2) ?
C10 C11 N . . 118.3(2) ?
C11 C10 C9 . . 117.8(2) ?
C12 C13 C8 . . 121.4(2) ?
C12 C11 N . . 119.3(2) ?
C13 C12 C11 . . 118.1(2) ?
C13 C8 C7 . . 119.8(2) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C7 O2 H2 . . 109.5 ?
C13 C12 H12 . . 120.9 ?
O2 C7 H7 . . 108.4 ?
C2 C7 H7 . . 108.4 ?
C8 C7 H7 . . 108.4 ?
C11 C12 H12 . . 120.9 ?
C12 C13 H13 . . 119.3 ?
C8 C13 H13 . . 119.3 ?
C11 C10 H10 . . 121.1 ?
C9 C10 H10 . . 121.1 ?
C2 C3 H3 . . 117.5 ?
C4 C3 H3 . . 117.5 ?
C5 C6 H6A . . 108.7 ?
C1 C6 H6A . . 108.7 ?
C5 C6 H6B . . 108.7 ?
C1 C6 H6B . . 108.7 ?
H6A C6 H6B . . 107.6 ?
C4 C5 H5A . . 109.3 ?
C6 C5 H5A . . 109.3 ?
C4 C5 H5B . . 109.3 ?
C6 C5 H5B . . 109.3 ?
H5A C5 H5B . . 107.9 ?
C5 C4 H4A . . 109.0 ?
C3 C4 H4A . . 109.0 ?
C5 C4 H4B . . 109.0 ?
C3 C4 H4B . . 109.0 ?
H4A C4 H4B . . 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 C1 . 1.214(3) y
O2 C7 . 1.413(3) y
C1 C2 . 1.477(3) y
C1 C6 . 1.510(4) y
C2 C3 . 1.313(3) y
C2 C7 . 1.514(3) y
C3 C4 . 1.491(3) y
C4 C5 . 1.472(4) y
C5 C6 . 1.507(4) y
C7 C8 . 1.532(3) y
C8 C13 . 1.387(3) ?
C9 C8 . 1.369(3) ?
C9 C10 . 1.394(3) ?
C11 C10 . 1.371(3) ?
C11 C12 . 1.381(3) ?
C12 C13 . 1.372(3) ?
N C11 . 1.472(3) ?
N O3 . 1.218(3) ?
N O4 . 1.224(3) ?
C7 H7 . 0.9800 ?
C9 H9 . 0.9300 ?
O2 H2 . 0.8200 ?
C12 H12 . 0.9300 ?
C13 H13 . 0.9300 ?
C10 H10 . 0.9300 ?
C3 H3 . 0.9300 ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C4 H4A . 0.9700 ?
C4 H4B . 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
O2 H2 O1 2_656 0.82 2.02 2.834(2) 171 y
C10 H10 O2 1_655 0.93 2.51 3.208(3) 132 y
C12 H12 O3 3_777 0.93 2.53 3.376(3) 152 y
C3 H3 O2 . 0.93 2.36 2.722(3) 103 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 N C11 C10 . . . . 178.1(2) ?
O4 N C11 C10 . . . . -2.8(3) ?
O3 N C11 C12 . . . . -1.4(3) ?
O4 N C11 C12 . . . . 177.7(2) ?
O2 C7 C2 C3 . . . . -17.1(3) ?
C8 C7 C2 C3 . . . . 105.9(3) ?
O2 C7 C2 C1 . . . . 157.83(19) ?
C8 C7 C2 C1 . . . . -79.2(2) ?
C10 C9 C8 C13 . . . . 0.1(3) ?
C10 C9 C8 C7 . . . . 176.0(2) ?
O2 C7 C8 C9 . . . . -120.3(2) ?
C2 C7 C8 C9 . . . . 118.5(2) ?
O2 C7 C8 C13 . . . . 55.5(3) ?
C2 C7 C8 C13 . . . . -65.7(3) ?
C10 C11 C12 C13 . . . . -0.1(4) ?
N C11 C12 C13 . . . . 179.4(2) ?
C3 C2 C1 O1 . . . . 174.4(2) ?
C7 C2 C1 O1 . . . . -0.8(3) ?
C3 C2 C1 C6 . . . . -0.1(3) ?
C7 C2 C1 C6 . . . . -175.3(2) ?
C11 C12 C13 C8 . . . . -0.2(4) ?
C9 C8 C13 C12 . . . . 0.3(3) ?
C7 C8 C13 C12 . . . . -175.7(2) ?
C12 C11 C10 C9 . . . . 0.4(3) ?
N C11 C10 C9 . . . . -179.06(19) ?
C8 C9 C10 C11 . . . . -0.4(3) ?
C1 C2 C3 C4 . . . . 4.6(4) ?
C7 C2 C3 C4 . . . . 179.3(2) ?
O1 C1 C6 C5 . . . . 158.4(3) ?
C2 C1 C6 C5 . . . . -27.1(3) ?
C1 C6 C5 C4 . . . . 49.6(4) ?
C6 C5 C4 C3 . . . . -44.7(4) ?
C2 C3 C4 C5 . . . . 18.9(4) ?