#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:20:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179573 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/38/4503860.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_4503860
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, C3 H6 O3'
_chemical_formula_sum            'C25 H24 F2 N2 O5'
_chemical_formula_weight         470.46
_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                 104.4040(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.5849(12)
_cell_length_b                   9.0737(7)
_cell_length_c                   16.6387(13)
_cell_measurement_reflns_used    2091
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.32
_cell_measurement_theta_min      2.53
_cell_volume                     2279.0(3)
_computing_cell_refinement       'APEX2 '
_computing_data_collection       'APEX2 '
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0239
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5427
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.95
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.371
_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          0.20
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2299
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0518P)²+1.5490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1061
_reflns_number_gt                1910
_reflns_number_total             2299
_reflns_threshold_expression     >2sigma
_cod_data_source_file            cg800658t_si_002.cif
_cod_data_source_block           a0705242tka(Form-IX)
_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               4503860
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
_atom_site_disorder_group
O4B O 0.4821(2) 0.3709(3) -0.00387(19) 0.0378(8) Uani 0.497(4) 1 d P 1
O4A O 0.59759(15) 0.5016(2) 0.04696(15) 0.0393(8) Uani 0.503(4) 1 d P 2
C12 C 0.5000 0.5000 0.0000 0.0461(7) Uani 1 2 d S .
C13 C 0.6253(2) 0.6419(3) 0.05456(18) 0.0718(7) Uani 1 1 d D .
O3 O 0.5287(2) 0.3815(3) 0.0152(2) 0.0413(7) Uani 0.50 1 d P .
C1 C 0.32424(9) 1.19125(16) 0.38144(8) 0.0239(3) Uani 1 1 d . .
H1 H 0.3289 1.2699 0.4200 0.029 Uiso 1 1 calc R .
C2 C 0.27552(9) 1.06712(16) 0.38753(9) 0.0238(3) Uani 1 1 d . .
C3 C 0.26618(9) 0.95024(16) 0.33343(9) 0.0267(3) Uani 1 1 d . .
H3 H 0.2306 0.8676 0.3388 0.032 Uiso 1 1 calc R .
C4 C 0.31040(9) 0.95674(15) 0.27063(9) 0.0236(3) Uani 1 1 d . .
H4 H 0.3063 0.8765 0.2332 0.028 Uiso 1 1 calc R .
C5 C 0.36072(8) 1.08017(14) 0.26209(8) 0.0194(3) Uani 1 1 d . .
C6 C 0.36636(9) 1.19775(15) 0.31712(8) 0.0218(3) Uani 1 1 d . .
H6 H 0.3993 1.2831 0.3106 0.026 Uiso 1 1 calc R .
C7 C 0.40111(9) 1.09877(15) 0.18999(8) 0.0208(3) Uani 1 1 d . .
C8 C 0.46344(10) 0.99377(17) 0.08308(8) 0.0266(3) Uani 1 1 d . .
H8A H 0.4145 0.9521 0.0403 0.040 Uiso 1 1 calc R .
H8B H 0.5180 0.9393 0.0841 0.040 Uiso 1 1 calc R .
H8C H 0.4714 1.0976 0.0705 0.040 Uiso 1 1 calc R .
C9 C 0.47102(8) 0.84958(14) 0.21032(8) 0.0194(3) Uani 1 1 d . .
C10 C 0.44370(9) 0.71539(16) 0.17164(9) 0.0257(3) Uani 1 1 d . .
H10 H 0.4051 0.7149 0.1175 0.031 Uiso 1 1 calc R .
C11 C 0.47171(10) 0.58253(16) 0.21059(10) 0.0310(4) Uani 1 1 d . .
H11 H 0.4522 0.4920 0.1834 0.037 Uiso 1 1 calc R .
F1 F 0.23447(6) 1.06037(10) 0.45074(5) 0.0344(3) Uani 1 1 d . .
N1 N 0.44298(7) 0.98211(12) 0.16458(7) 0.0202(3) Uani 1 1 d . .
O1 O 0.39277(7) 1.21629(11) 0.15240(6) 0.0312(3) Uani 1 1 d . .
H13 H 0.617(2) 0.684(3) 0.1035(15) 0.121(12) Uiso 1 1 d D .
H14 H 0.633(2) 0.719(3) 0.0194(19) 0.140(14) Uiso 1 1 d D .
H15 H 0.686(2) 0.605(7) 0.073(4) 0.28(3) Uiso 1 1 d 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
C12 O4B C13 106.4(2) . 5_665
C13 O4A C12 108.3(2) . .
O3 C12 O3 180.0(3) 5_665 .
O3 C12 O4B 35.49(14) 5_665 5_665
O3 C12 O4B 144.51(14) . 5_665
O3 C12 O4B 144.51(14) 5_665 .
O3 C12 O4B 35.49(14) . .
O4B C12 O4B 180.0 5_665 .
O3 C12 O4A 112.42(19) 5_665 .
O3 C12 O4A 67.58(19) . .
O4B C12 O4A 77.02(18) 5_665 .
O4B C12 O4A 102.98(18) . .
O3 C12 O4A 67.58(19) 5_665 5_665
O3 C12 O4A 112.42(19) . 5_665
O4B C12 O4A 102.98(18) 5_665 5_665
O4B C12 O4A 77.02(18) . 5_665
O4A C12 O4A 180.00(18) . 5_665
O4A C13 O4B 68.3(2) . 5_665
O4A C13 H13 111(2) . .
O4B C13 H13 98(2) 5_665 .
O4A C13 H14 137(2) . .
O4B C13 H14 90(2) 5_665 .
H13 C13 H14 108(3) . .
O4A C13 H15 88(4) . .
O4B C13 H15 154(4) 5_665 .
H13 C13 H15 101(4) . .
H14 C13 H15 101(4) . .
C2 C1 C6 117.82(13) . .
C2 C1 H1 121.1 . .
C6 C1 H1 121.1 . .
F1 C2 C3 118.51(12) . .
F1 C2 C1 117.88(12) . .
C3 C2 C1 123.60(13) . .
C2 C3 C4 117.92(13) . .
C2 C3 H3 121.0 . .
C4 C3 H3 121.0 . .
C3 C4 C5 120.51(13) . .
C3 C4 H4 119.7 . .
C5 C4 H4 119.7 . .
C6 C5 C4 119.52(12) . .
C6 C5 C7 118.02(12) . .
C4 C5 C7 122.11(12) . .
C1 C6 C5 120.58(12) . .
C1 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
O1 C7 N1 120.97(12) . .
O1 C7 C5 119.63(12) . .
N1 C7 C5 119.32(11) . .
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 . .
C10 C9 C9 119.09(8) . 2_655
C10 C9 N1 118.07(12) . .
C9 C9 N1 122.71(7) 2_655 .
C11 C10 C9 121.28(14) . .
C11 C10 H10 119.4 . .
C9 C10 H10 119.4 . .
C11 C11 C10 119.62(9) 2_655 .
C11 C11 H11 120.2 2_655 .
C10 C11 H11 120.2 . .
C7 N1 C9 126.36(11) . .
C7 N1 C8 117.35(11) . .
C9 N1 C8 116.27(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O4B C12 1.202(3) .
O4B C13 1.680(5) 5_665
O4A C13 1.340(3) .
O4A C12 1.527(2) .
C12 O3 1.168(3) 5_665
C12 O3 1.168(3) .
C12 O4B 1.202(3) 5_665
C12 O4A 1.527(2) 5_665
C13 O4B 1.680(5) 5_665
C13 H13 0.935(18) .
C13 H14 0.938(18) .
C13 H15 0.97(2) .
C1 C2 1.376(2) .
C1 C6 1.3889(19) .
C1 H1 0.9500 .
C2 F1 1.3615(15) .
C2 C3 1.375(2) .
C3 C4 1.389(2) .
C3 H3 0.9500 .
C4 C5 1.3946(19) .
C4 H4 0.9500 .
C5 C6 1.3944(19) .
C5 C7 1.4966(18) .
C6 H6 0.9500 .
C7 O1 1.2266(17) .
C7 N1 1.3647(17) .
C8 N1 1.4720(17) .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.3935(19) .
C9 C9 1.402(3) 2_655
C9 N1 1.4320(17) .
C10 C11 1.387(2) .
C10 H10 0.9500 .
C11 C11 1.386(3) 2_655
C11 H11 0.9500 .
