#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/04/2230403.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_2230403
loop_
_publ_author_name
'Huang, Chang-Jiang'
'Wu, Jiang'
'Cai, Zhi-Qiang'
'Yuan, Jing'
_publ_section_title
;
 4-(3-Fluoro-4-nitrophenyl)morpholin-3-one
;
_journal_coeditor_code           KP2328
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1549
_journal_paper_doi               10.1107/S1600536811019738
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C10 H9 F N2 O4'
_chemical_formula_moiety         'C10 H9 F N2 O4'
_chemical_formula_sum            'C10 H9 F N2 O4'
_chemical_formula_weight         240.19
_chemical_name_systematic
;
4-(3-Fluoro-4-nitrophenyl)morpholin-3-one
;
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                73.30(3)
_cell_angle_beta                 75.39(3)
_cell_angle_gamma                74.30(3)
_cell_formula_units_Z            2
_cell_length_a                   6.6408(7)
_cell_length_b                   7.3788(10)
_cell_length_c                   10.8546(14)
_cell_measurement_reflns_used    1909
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      31.1
_cell_measurement_theta_min      2.0
_cell_volume                     481.59(14)
_computing_cell_refinement       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'RAPID-AUTO (Rigaku, 1998)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure (Rigaku/MSC, 2009)'
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0623
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6470
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         1.99
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku/MSC, 2009)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0392
_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)+(0.0502P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1039
_reflns_number_gt                1734
_reflns_number_total             2569
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            kp2328.cif
_cod_data_source_block           I
_cod_original_cell_volume        481.60(14)
_cod_database_code               2230403
_cod_database_fobs_code          2230403
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_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.38071(13) 0.73231(13) -0.24062(8) 0.0292(2) Uani d . 1 1 . .
O O1 0.23003(15) 0.94560(12) 0.40672(8) 0.0192(2) Uani d . 1 1 . .
O O2 0.04787(15) 0.82852(15) 0.16307(9) 0.0262(2) Uani d . 1 1 . .
O O3 0.74637(16) 0.59970(13) -0.37865(9) 0.0241(2) Uani d . 1 1 . .
O O4 1.03428(15) 0.62270(13) -0.32888(9) 0.0234(2) Uani d . 1 1 . .
N N1 0.39251(16) 0.79057(14) 0.18692(10) 0.0139(2) Uani d . 1 1 . .
N N2 0.84043(18) 0.63168(15) -0.30564(10) 0.0165(2) Uani d . 1 1 . .
C C1 0.5325(2) 0.77071(18) 0.27977(12) 0.0161(3) Uani d . 1 1 . .
H H1A 0.6152 0.8739 0.2456 0.019 Uiso calc R 1 1 . .
H H1B 0.6347 0.6443 0.2855 0.019 Uiso calc R 1 1 . .
C C2 0.4068(2) 0.78419(19) 0.41571(12) 0.0201(3) Uani d . 1 1 . .
H H2A 0.3550 0.6634 0.4599 0.024 Uiso calc R 1 1 . .
H H2B 0.5001 0.7996 0.4685 0.024 Uiso calc R 1 1 . .
C C3 0.0821(2) 0.90024(19) 0.35316(12) 0.0183(3) Uani d . 1 1 . .
H H3A -0.0349 1.0155 0.3382 0.022 Uiso calc R 1 1 . .
H H3B 0.0196 0.7956 0.4183 0.022 Uiso calc R 1 1 . .
C C4 0.1736(2) 0.83638(18) 0.22515(12) 0.0164(3) Uani d . 1 1 . .
C C5 0.4968(2) 0.75696(16) 0.06139(12) 0.0132(3) Uani d . 1 1 . .
C C6 0.7205(2) 0.71941(17) 0.03016(12) 0.0160(3) Uani d . 1 1 . .
H H6 0.7988 0.7192 0.0924 0.019 Uiso calc R 1 1 . .
C C7 0.8283(2) 0.68282(17) -0.09000(12) 0.0161(3) Uani d . 1 1 . .
H H7 0.9795 0.6591 -0.1095 0.019 Uiso calc R 1 1 . .
C C8 0.7182(2) 0.68025(17) -0.18264(12) 0.0143(3) Uani d . 1 1 . .
C C9 0.4967(2) 0.72366(18) -0.15317(12) 0.0158(3) Uani d . 1 1 . .
C C10 0.3858(2) 0.76283(17) -0.03458(12) 0.0160(3) Uani d . 1 1 . .
H H10 0.2345 0.7938 -0.0178 0.019 Uiso calc R 1 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'
F F 0.0171 0.0103 '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 O1 C2 . . 107.55(9) ?
C4 N1 C5 . . 123.48(11) ?
C4 N1 C1 . . 120.11(10) ?
C5 N1 C1 . . 116.39(10) ?
O3 N2 O4 . . 123.82(11) ?
O3 N2 C8 . . 118.74(11) ?
O4 N2 C8 . . 117.43(10) ?
N1 C1 C2 . . 112.26(10) ?
N1 C1 H1A . . 109.2 ?
C2 C1 H1A . . 109.2 ?
N1 C1 H1B . . 109.2 ?
C2 C1 H1B . . 109.2 ?
H1A C1 H1B . . 107.9 ?
O1 C2 C1 . . 109.95(10) ?
O1 C2 H2A . . 109.7 ?
C1 C2 H2A . . 109.7 ?
O1 C2 H2B . . 109.7 ?
C1 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
O1 C3 C4 . . 114.95(11) ?
O1 C3 H3A . . 108.5 ?
C4 C3 H3A . . 108.5 ?
O1 C3 H3B . . 108.5 ?
C4 C3 H3B . . 108.5 ?
H3A C3 H3B . . 107.5 ?
O2 C4 N1 . . 124.24(12) ?
O2 C4 C3 . . 117.50(12) ?
N1 C4 C3 . . 118.25(11) ?
C10 C5 C6 . . 118.08(11) ?
C10 C5 N1 . . 122.88(11) ?
C6 C5 N1 . . 119.03(11) ?
C7 C6 C5 . . 120.88(12) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 120.88(12) ?
C6 C7 H7 . . 119.6 ?
C8 C7 H7 . . 119.6 ?
C7 C8 C9 . . 118.10(12) ?
C7 C8 N2 . . 118.60(11) ?
C9 C8 N2 . . 123.31(11) ?
F1 C9 C10 . . 116.88(12) ?
F1 C9 C8 . . 121.12(12) ?
C10 C9 C8 . . 121.99(12) ?
C9 C10 C5 . . 119.97(12) ?
C9 C10 H10 . . 120.0 ?
C5 C10 H10 . . 120.0 ?
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
F1 C9 . 1.3438(13) ?
O1 C3 . 1.4118(14) ?
O1 C2 . 1.4286(16) ?
O2 C4 . 1.2193(14) ?
O3 N2 . 1.2292(13) ?
O4 N2 . 1.2349(13) ?
N1 C4 . 1.3823(16) ?
N1 C5 . 1.4223(16) ?
N1 C1 . 1.4885(15) ?
N2 C8 . 1.4630(16) ?
C1 C2 . 1.5171(18) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.5223(18) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C5 C10 . 1.4050(16) ?
C5 C6 . 1.4061(18) ?
C6 C7 . 1.3831(17) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.3910(16) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.3912(18) ?
C9 C10 . 1.3795(18) ?
C10 H10 . 0.9500 ?
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
C6 H6 O2 1_655 0.95 2.39 3.2635(16) 153 y
C2 H2B O3 1_556 0.99 2.50 3.3244(19) 140 y
C1 H1B O4 2_765 0.99 2.57 3.515(2) 161 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
C4 N1 C1 C2 . . . . 6.24(15) ?
C5 N1 C1 C2 . . . . -172.77(10) ?
C3 O1 C2 C1 . . . . 70.39(13) ?
N1 C1 C2 O1 . . . . -46.84(14) ?
C2 O1 C3 C4 . . . . -52.83(13) ?
C5 N1 C4 O2 . . . . 9.8(2) ?
C1 N1 C4 O2 . . . . -169.11(11) ?
C5 N1 C4 C3 . . . . -170.40(11) ?
C1 N1 C4 C3 . . . . 10.66(17) ?
O1 C3 C4 O2 . . . . -167.37(11) ?
O1 C3 C4 N1 . . . . 12.84(16) ?
C4 N1 C5 C10 . . . . -1.57(18) ?
C1 N1 C5 C10 . . . . 177.41(11) ?
C4 N1 C5 C6 . . . . 177.30(11) ?
C1 N1 C5 C6 . . . . -3.73(16) ?
C10 C5 C6 C7 . . . . -2.16(18) ?
N1 C5 C6 C7 . . . . 178.93(10) ?
C5 C6 C7 C8 . . . . -0.66(19) ?
C6 C7 C8 C9 . . . . 2.70(19) ?
C6 C7 C8 N2 . . . . -177.12(11) ?
O3 N2 C8 C7 . . . . 168.82(11) ?
O4 N2 C8 C7 . . . . -10.19(16) ?
O3 N2 C8 C9 . . . . -10.99(18) ?
O4 N2 C8 C9 . . . . 170.00(11) ?
C7 C8 C9 F1 . . . . 176.97(10) ?
N2 C8 C9 F1 . . . . -3.22(19) ?
C7 C8 C9 C10 . . . . -1.95(19) ?
N2 C8 C9 C10 . . . . 177.87(11) ?
F1 C9 C10 C5 . . . . -179.83(10) ?
C8 C9 C10 C5 . . . . -0.87(19) ?
C6 C5 C10 C9 . . . . 2.90(18) ?
N1 C5 C10 C9 . . . . -178.23(11) ?
