#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:20:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179573 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503859.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_4503859
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, C6 H6'
_chemical_formula_sum            'C28 H24 F2 N2 O2'
_chemical_formula_weight         458.49
_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                 104.4450(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.8040(12)
_cell_length_b                   8.9673(8)
_cell_length_c                   21.308(2)
_cell_measurement_reflns_used    1436
_cell_measurement_temperature    120
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.80
_cell_volume                     2369.2(4)
_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      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.975
_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  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0320
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5618
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.25
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9819
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0385
_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)+(0.0370P)²+1.2548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0845
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                1789
_reflns_number_total             2339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg800658t_si_002.cif
_cod_data_source_block           a0705212tka(Form-VIII)
_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               4503859
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
C7 C 0.37319(11) 1.05852(15) 0.72876(7) 0.0197(3) Uani 1 1 d .
C10 C 0.40233(11) 0.66725(15) 0.70509(7) 0.0197(3) Uani 1 1 d .
H10 H 0.3348 0.6667 0.6739 0.024 Uiso 1 1 calc R
C5 C 0.37248(11) 1.04561(15) 0.79849(7) 0.0186(3) Uani 1 1 d .
C9 C 0.45001(11) 0.80323(14) 0.72702(6) 0.0155(3) Uani 1 1 d .
C3 C 0.39986(12) 1.16479(18) 0.90285(8) 0.0297(4) Uani 1 1 d .
H3 H 0.4245 1.2465 0.9311 0.036 Uiso 1 1 calc R
C8 C 0.37672(12) 0.94229(17) 0.62626(7) 0.0241(3) Uani 1 1 d .
H8A H 0.3065 0.8964 0.6071 0.036 Uiso 1 1 calc R
H8B H 0.4332 0.8879 0.6121 0.036 Uiso 1 1 calc R
H8C H 0.3759 1.0464 0.6122 0.036 Uiso 1 1 calc R
C6 C 0.32808(11) 0.92231(15) 0.82194(7) 0.0203(3) Uani 1 1 d .
H6 H 0.3040 0.8394 0.7944 0.024 Uiso 1 1 calc R
C4 C 0.40642(12) 1.16770(17) 0.83921(7) 0.0246(3) Uani 1 1 d .
H4 H 0.4343 1.2536 0.8229 0.029 Uiso 1 1 calc R
C1 C 0.31883(12) 0.91992(17) 0.88521(7) 0.0252(4) Uani 1 1 d .
H1 H 0.2872 0.8371 0.9013 0.030 Uiso 1 1 calc R
C11 C 0.45040(12) 0.53287(16) 0.72740(7) 0.0223(3) Uani 1 1 d .
H11 H 0.4160 0.4414 0.7120 0.027 Uiso 1 1 calc R
C2 C 0.35655(12) 1.04019(19) 0.92423(7) 0.0291(4) Uani 1 1 d .
C13 C 0.10263(14) 0.05872(19) 0.51654(8) 0.0359(4) Uani 1 1 d .
H13 H 0.1734 0.0993 0.5279 0.043 Uiso 1 1 calc R
C12 C 0.03750(15) 0.07007(19) 0.55899(9) 0.0372(4) Uani 1 1 d .
H12 H 0.0634 0.1182 0.5996 0.045 Uiso 1 1 calc R
C14 C 0.06544(14) -0.01133(19) 0.45769(8) 0.0374(4) Uani 1 1 d .
H14 H 0.1106 -0.0193 0.4286 0.045 Uiso 1 1 calc R
F1 F 0.34855(8) 1.03680(12) 0.98664(4) 0.0462(3) Uani 1 1 d .
O1 O 0.34673(9) 1.17661(11) 0.69970(5) 0.0293(3) Uani 1 1 d .
N1 N 0.39862(9) 0.93640(12) 0.69737(5) 0.0180(3) Uani 1 1 d .
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
O1 C7 N1 120.89(13) . .
O1 C7 C5 119.88(13) . .
N1 C7 C5 119.16(12) . .
C11 C10 C9 121.88(13) . .
C11 C10 H10 119.1 . .
C9 C10 H10 119.1 . .
C6 C5 C4 119.42(14) . .
C6 C5 C7 121.56(13) . .
C4 C5 C7 118.63(13) . .
C10 C9 C9 118.78(8) . 2_656
C10 C9 N1 117.89(12) . .
C9 C9 N1 123.11(7) 2_656 .
C2 C3 C4 118.01(14) . .
C2 C3 H3 121.0 . .
C4 C3 H3 121.0 . .
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 . .
C1 C6 C5 120.29(14) . .
C1 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C3 C4 C5 120.65(14) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C2 C1 C6 118.37(14) . .
C2 C1 H1 120.8 . .
C6 C1 H1 120.8 . .
C10 C11 C11 119.34(8) . 2_656
C10 C11 H11 120.3 . .
C11 C11 H11 120.3 2_656 .
F1 C2 C1 118.27(15) . .
F1 C2 C3 118.53(15) . .
C1 C2 C3 123.19(14) . .
C14 C13 C12 120.19(16) . .
C14 C13 H13 119.9 . .
C12 C13 H13 119.9 . .
C13 C12 C14 119.84(16) . 5_556
C13 C12 H12 120.1 . .
C14 C12 H12 120.1 5_556 .
C13 C14 C12 119.97(17) . 5_556
C13 C14 H14 120.0 . .
C12 C14 H14 120.0 5_556 .
C7 N1 C9 126.34(11) . .
C7 N1 C8 117.95(11) . .
C9 N1 C8 115.64(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C7 O1 1.2309(16) .
C7 N1 1.3642(17) .
C7 C5 1.493(2) .
C10 C11 1.3824(19) .
C10 C9 1.3912(19) .
C10 H10 0.9500 .
C5 C6 1.3917(19) .
C5 C4 1.397(2) .
C9 C9 1.404(3) 2_656
C9 N1 1.4321(16) .
C3 C2 1.375(2) .
C3 C4 1.380(2) .
C3 H3 0.9500 .
C8 N1 1.4715(18) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C6 C1 1.383(2) .
C6 H6 0.9500 .
C4 H4 0.9500 .
C1 C2 1.374(2) .
C1 H1 0.9500 .
C11 C11 1.389(3) 2_656
C11 H11 0.9500 .
C2 F1 1.3593(17) .
C13 C14 1.377(2) .
C13 C12 1.379(2) .
C13 H13 0.9500 .
C12 C14 1.381(2) 5_556
C12 H12 0.9500 .
C14 C12 1.381(2) 5_556
C14 H14 0.9500 .
