#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:42:48 +0200 (vie 13 de oct de 2017) $
#$Revision: 201978 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/02/2220242.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_2220242
loop_
_publ_author_name
'Li, Xin-Hua'
'Wang, De-Cai'
'Liu, Bo-Nian'
'Xu, Wei'
_publ_section_title
;
 (4S,5S)-2-(2-Fluorophenyl)-1,3-dioxolane-4,5-dicarboxamide
;
_journal_coeditor_code           HK2584
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2499
_journal_paper_doi               10.1107/S1600536808039470
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H11 F N2 O4'
_chemical_formula_moiety         'C11 H11 F N2 O4'
_chemical_formula_sum            'C11 H11 F N2 O4'
_chemical_formula_weight         254.22
_chemical_name_systematic
;
(4S,5S)-2-(2-Fluorophenyl)-1,3-dioxolane-4,5-dicarboxamide
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8760(5)
_cell_length_b                   9.1290(7)
_cell_length_c                   24.8160(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      12
_cell_measurement_theta_min      9
_cell_volume                     1104.63(15)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0722
_diffrn_reflns_av_sigmaI/netI    0.0934
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2157
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1301
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0597
_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)+(0.002P)²+1.775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1069
_refine_ls_wR_factor_ref         0.1246
_reflns_number_gt                898
_reflns_number_total             1301
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2584.cif
_cod_data_source_block           I
_cod_database_code               2220242
_cod_database_fobs_code          2220242
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
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
O O1 0.6898(8) 0.3384(4) 0.36430(13) 0.0497(10) Uani d . 1
O O2 0.9373(9) 0.5438(3) 0.37339(12) 0.0489(10) Uani d . 1
O O3 1.1580(8) 0.2201(5) 0.44108(17) 0.0576(11) Uani d . 1
O O4 0.7161(10) 0.6057(4) 0.50750(13) 0.0599(12) Uani d . 1
N N1 0.7627(11) 0.0954(4) 0.44684(15) 0.0513(12) Uani d . 1
H H1A 0.8450 0.0144 0.4540 0.062 Uiso calc R 1
H H1B 0.5866 0.0979 0.4449 0.062 Uiso calc R 1
N N2 0.5605(12) 0.6946(5) 0.42850(18) 0.0681(16) Uani d . 1
H H2A 0.4529 0.7561 0.4441 0.082 Uiso calc R 1
H H2B 0.5674 0.6905 0.3939 0.082 Uiso calc R 1
F F1 0.4814(11) 0.6150(5) 0.30682(15) 0.1054(16) Uani d . 1
C C1 0.6335(15) 0.5470(7) 0.2681(2) 0.0633(18) Uani d . 1
C C2 0.572(2) 0.5797(8) 0.2158(3) 0.083(2) Uani d . 1
H H2 0.4353 0.6472 0.2076 0.099 Uiso calc R 1
C C3 0.715(2) 0.5109(8) 0.1758(3) 0.088(3) Uani d . 1
H H3 0.6700 0.5274 0.1399 0.105 Uiso calc R 1
C C4 0.9265(19) 0.4170(9) 0.1887(2) 0.095(3) Uani d . 1
H H4 1.0286 0.3731 0.1615 0.114 Uiso calc R 1
C C5 0.9875(19) 0.3878(8) 0.2426(2) 0.076(2) Uani d . 1
H H5 1.1281 0.3230 0.2511 0.092 Uiso calc R 1
C C6 0.8410(14) 0.4542(6) 0.2832(2) 0.0539(16) Uani d . 1
C C7 0.9126(13) 0.4196(6) 0.34082(18) 0.0466(13) Uani d . 1
H H7 1.0818 0.3617 0.3423 0.056 Uiso calc R 1
C C8 0.7392(14) 0.3487(5) 0.42137(18) 0.0461(14) Uani d . 1
H H8 0.5644 0.3507 0.4409 0.055 Uiso calc R 1
C C9 0.8871(13) 0.4968(5) 0.42764(19) 0.0470(14) Uani d . 1
H H9 1.0617 0.4826 0.4465 0.056 Uiso calc R 1
C C10 0.9067(11) 0.2163(6) 0.4389(2) 0.0407(12) Uani d . 1
C C11 0.7142(14) 0.6068(5) 0.4576(2) 0.0492(14) Uani d . 1
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
O1 0.056(2) 0.0459(19) 0.0467(19) -0.007(2) -0.009(2) 0.0041(16)
O2 0.059(2) 0.0420(18) 0.0451(19) -0.007(2) 0.006(2) -0.0011(15)
O3 0.038(2) 0.059(2) 0.075(3) -0.006(2) -0.003(2) 0.007(2)
O4 0.079(3) 0.054(2) 0.046(2) -0.016(3) 0.003(2) -0.0063(17)
N1 0.055(3) 0.044(2) 0.055(2) -0.001(3) -0.009(3) 0.008(2)
N2 0.093(4) 0.060(3) 0.052(3) 0.020(4) 0.000(3) -0.004(2)
F1 0.106(4) 0.128(4) 0.082(3) 0.045(4) -0.016(3) 0.000(3)
C1 0.071(5) 0.066(4) 0.054(3) 0.003(4) -0.003(3) 0.005(3)
C2 0.106(6) 0.072(4) 0.070(4) -0.004(5) -0.022(5) 0.017(4)
C3 0.118(7) 0.091(5) 0.053(4) -0.021(6) -0.021(5) 0.021(4)
C4 0.108(6) 0.134(7) 0.043(3) -0.003(7) 0.000(4) -0.005(4)
C5 0.088(5) 0.087(5) 0.054(4) 0.010(5) 0.009(4) -0.010(3)
C6 0.068(4) 0.048(3) 0.046(3) -0.003(3) 0.000(3) 0.005(2)
C7 0.048(3) 0.047(3) 0.045(3) 0.002(3) 0.001(3) 0.000(2)
C8 0.063(4) 0.037(2) 0.038(3) 0.003(3) -0.002(3) 0.002(2)
C9 0.056(4) 0.042(3) 0.043(3) 0.001(3) 0.002(3) 0.003(2)
C10 0.045(3) 0.039(3) 0.038(3) 0.001(3) 0.001(3) -0.002(2)
C11 0.062(4) 0.039(3) 0.047(3) -0.009(3) 0.002(3) -0.006(2)
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 0.0000 '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'
F F 0.0171 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C7 O1 C8 103.8(4)
C7 O2 C9 106.6(3)
C10 N1 H1A 120.0
C10 N1 H1B 120.0
H1A N1 H1B 120.0
C11 N2 H2A 120.0
C11 N2 H2B 120.0
H2A N2 H2B 120.0
F1 C1 C2 116.8(7)
F1 C1 C6 119.4(5)
C2 C1 C6 123.9(7)
C1 C2 C3 118.5(7)
C1 C2 H2 120.8
C3 C2 H2 120.8
C2 C3 C4 119.9(6)
C2 C3 H3 120.0
C4 C3 H3 120.0
C3 C4 C5 120.1(7)
C3 C4 H4 120.0
C5 C4 H4 120.0
C6 C5 C4 120.5(7)
C6 C5 H5 119.8
C4 C5 H5 119.8
C1 C6 C5 117.1(6)
C1 C6 C7 124.1(5)
C5 C6 C7 118.9(6)
O1 C7 C6 108.5(5)
O1 C7 H7 110.1
O2 C7 O1 104.4(4)
O2 C7 C6 113.5(4)
O2 C7 H7 110.1
C6 C7 H7 110.1
O1 C8 C10 108.6(4)
O1 C8 C9 103.6(4)
O1 C8 H8 109.9
C9 C8 H8 109.9
C10 C8 C9 114.6(5)
C10 C8 H8 109.9
O2 C9 C8 104.3(4)
O2 C9 C11 111.0(4)
O2 C9 H9 109.8
C8 C9 H9 109.8
C11 C9 C8 111.9(5)
C11 C9 H9 109.8
O3 C10 N1 123.2(6)
O3 C10 C8 121.8(5)
O4 C11 N2 123.9(6)
O4 C11 C9 118.9(5)
N1 C10 C8 114.8(4)
N2 C11 C9 117.1(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.438(6)
O1 C8 1.440(5)
O2 C7 1.398(5)
O2 C9 1.434(5)
O3 C10 1.227(6)
O4 C11 1.240(5)
N1 C10 1.323(6)
N1 H1A 0.8600
N1 H1B 0.8600
N2 H2A 0.8600
N2 H2B 0.8600
F1 C1 1.363(7)
C2 C1 1.366(7)
C2 H2 0.9300
C3 C2 1.367(10)
C3 C4 1.378(11)
C3 H3 0.9300
C4 H4 0.9300
C5 C4 1.396(8)
C5 H5 0.9300
C6 C1 1.372(8)
C6 C5 1.376(8)
C7 C6 1.505(7)
C7 H7 0.9800
C8 H8 0.9800
C9 C8 1.540(7)
C9 H9 0.9800
C10 C8 1.522(7)
C11 N2 1.313(7)
C11 C9 1.507(7)
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
N1 H1A O4 3_556 0.86 2.32 3.089(4) 149 yes
N1 H1B O3 1_455 0.86 2.37 3.164(4) 153 yes
N2 H2A O4 3_466 0.86 2.09 2.944(5) 172 yes
N2 H2B F1 . 0.86 2.31 3.130(4) 160 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741267
