#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:20:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179573 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503858.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_4503858
loop_
_publ_author_name
'Kato, Takako'
'Okamoto, Iwao'
'Masu, Hyuma'
'Katagiri, Kosuke'
'Tominaga, Masahide'
'Yamaguchi, Kentaro'
'Kagechika, Hiroyuki'
'Azumaya, Isao'
_publ_section_title
;
 Polymorphism and Pseudopolymorphism of an Aromatic Amide: Spontaneous
 Resolution and Crystal-to-Crystal phase Transition
;
_journal_issue                   10
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3871
_journal_paper_doi               10.1021/cg800658t
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         'C22 H18 F2 N2 O2, C4 H8 O2'
_chemical_formula_sum            'C26 H26 F2 N2 O4'
_chemical_formula_weight         468.49
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_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                 103.286(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.763(2)
_cell_length_b                   9.1631(15)
_cell_length_c                   20.309(5)
_cell_measurement_reflns_used    2198
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      2.76
_cell_volume                     2311.5(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'Bruker ApexII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0880
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4522
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9899
_exptl_absorpt_correction_T_min  0.9800
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0011(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2278
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0450
_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)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1694
_reflns_number_gt                1573
_reflns_number_total             2278
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800658t_si_002.cif
_cod_data_source_block           a0704271tka(Form-VII)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4503858
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
F1 F 0.16644(11) 0.41051(15) 0.00190(6) 0.0303(4) Uani 1 1 d .
O1 O 0.14679(13) 0.57096(15) 0.29790(7) 0.0250(4) Uani 1 1 d .
N1 N 0.10013(15) 0.33357(17) 0.30389(7) 0.0159(4) Uani 1 1 d .
C9 C 0.04915(16) 0.20228(19) 0.27365(9) 0.0135(5) Uani 1 1 d .
C10 C 0.09735(18) 0.0688(2) 0.29666(9) 0.0170(5) Uani 1 1 d .
H10 H 0.1644 0.0682 0.3288 0.020 Uiso 1 1 calc R
C11 C 0.04865(17) -0.0625(2) 0.27321(9) 0.0178(5) Uani 1 1 d .
H11 H 0.0824 -0.1522 0.2892 0.021 Uiso 1 1 calc R
C8 C 0.12158(19) 0.3418(2) 0.37823(9) 0.0202(5) Uani 1 1 d .
H8A H 0.1911 0.2960 0.3979 0.030 Uiso 1 1 calc R
H8B H 0.0645 0.2905 0.3940 0.030 Uiso 1 1 calc R
H8C H 0.1234 0.4442 0.3923 0.030 Uiso 1 1 calc R
C7 C 0.12431(18) 0.4526(2) 0.26953(10) 0.0176(5) Uani 1 1 d .
C5 C 0.12975(17) 0.4345(2) 0.19712(9) 0.0157(5) Uani 1 1 d .
C6 C 0.17805(17) 0.3128(2) 0.17576(9) 0.0164(5) Uani 1 1 d .
H6 H 0.2017 0.2347 0.2063 0.020 Uiso 1 1 calc R
C1 C 0.19183(18) 0.3050(2) 0.10997(10) 0.0197(5) Uani 1 1 d .
H1 H 0.2260 0.2232 0.0952 0.024 Uiso 1 1 calc R
C2 C 0.15468(19) 0.4189(2) 0.06685(9) 0.0213(5) Uani 1 1 d .
C3 C 0.10726(19) 0.5426(2) 0.08607(10) 0.0237(5) Uani 1 1 d .
H3 H 0.0830 0.6195 0.0549 0.028 Uiso 1 1 calc R
C4 C 0.09618(19) 0.5506(2) 0.15250(11) 0.0219(5) Uani 1 1 d .
H4 H 0.0657 0.6353 0.1677 0.026 Uiso 1 1 calc R
O2 O 0.53238(15) 0.35253(16) 0.00701(8) 0.0330(5) Uani 1 1 d .
C12 C 0.4586(2) 0.4130(3) 0.04332(13) 0.0399(7) Uani 1 1 d .
H12A H 0.4989 0.4489 0.0879 0.048 Uiso 1 1 calc R
H12B H 0.4082 0.3363 0.0511 0.048 Uiso 1 1 calc R
C13 C 0.6030(2) 0.4647(3) -0.00450(14) 0.0378(7) Uani 1 1 d .
H13A H 0.6539 0.4245 -0.0300 0.045 Uiso 1 1 calc R
H13B H 0.6453 0.5015 0.0394 0.045 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 C9 125.64(16) . .
C7 N1 C8 118.13(16) . .
C9 N1 C8 116.12(15) . .
C9 C9 C10 119.14(12) 2 .
C9 C9 N1 122.83(10) 2 .
C10 C9 N1 117.88(17) . .
C11 C10 C9 121.01(19) . .
C11 C10 H10 119.5 . .
C9 C10 H10 119.5 . .
C11 C11 C10 119.85(12) 2 .
C11 C11 H11 120.1 2 .
C10 C11 H11 120.1 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O1 C7 N1 121.30(18) . .
O1 C7 C5 119.95(17) . .
N1 C7 C5 118.64(16) . .
C6 C5 C4 119.96(18) . .
C6 C5 C7 121.28(17) . .
C4 C5 C7 118.37(18) . .
C1 C6 C5 120.29(17) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C2 C1 C6 118.19(19) . .
C2 C1 H1 120.9 . .
C6 C1 H1 120.9 . .
F1 C2 C1 118.33(19) . .
F1 C2 C3 118.19(17) . .
C1 C2 C3 123.47(19) . .
C2 C3 C4 117.80(18) . .
C2 C3 H3 121.1 . .
C4 C3 H3 121.1 . .
C3 C4 C5 120.23(19) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C13 O2 C12 108.72(18) . .
O2 C12 C13 110.4(2) . 5_665
O2 C12 H12A 109.6 . .
C13 C12 H12A 109.6 5_665 .
O2 C12 H12B 109.6 . .
C13 C12 H12B 109.6 5_665 .
H12A C12 H12B 108.1 . .
O2 C13 C12 110.8(2) . 5_665
O2 C13 H13A 109.5 . .
C12 C13 H13A 109.5 5_665 .
O2 C13 H13B 109.5 . .
C12 C13 H13B 109.5 5_665 .
H13A C13 H13B 108.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.364(2) .
O1 C7 1.230(2) .
N1 C7 1.368(3) .
N1 C9 1.437(2) .
N1 C8 1.473(2) .
C9 C9 1.394(4) 2
C9 C10 1.400(3) .
C10 C11 1.388(3) .
C10 H10 0.9500 .
C11 C11 1.376(4) 2
C11 H11 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C7 C5 1.497(3) .
C5 C6 1.391(3) .
C5 C4 1.400(3) .
C6 C1 1.389(3) .
C6 H6 0.9500 .
C1 C2 1.375(3) .
C1 H1 0.9500 .
C2 C3 1.382(3) .
C3 C4 1.390(3) .
C3 H3 0.9500 .
C4 H4 0.9500 .
O2 C13 1.421(3) .
O2 C12 1.434(3) .
C12 C13 1.487(4) 5_665
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C12 1.487(4) 5_665
C13 H13A 0.9900 .
C13 H13B 0.9900 .
