#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/94/2229410.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_2229410
loop_
_publ_author_name
'Baur, Benjamin'
'Schollmeyer, Dieter'
'Laufer, Stefan'
_publ_section_title
;
 3-(2,4-Difluoroanilino)-9-nitrodibenzo[b,e]oxepin-11(6H)-one
;
_journal_coeditor_code           IM2261
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o555
_journal_paper_doi               10.1107/S1600536811002881
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C20 H12 F2 N2 O4'
_chemical_formula_moiety         'C20 H12 F2 N2 O4'
_chemical_formula_sum            'C20 H12 F2 N2 O4'
_chemical_formula_weight         382.32
_chemical_name_systematic
;
3-(2,4-Difluoroanilino)-9-nitrodibenzo[b,e]oxepin-
11(6H)-one
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 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                   27.0813(15)
_cell_length_b                   13.0411(8)
_cell_length_c                   4.5998(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      69
_cell_measurement_theta_min      65
_cell_volume                     1624.51(15)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1989)'
_computing_data_reduction        'CORINC (Dräger & Gattow, 1971)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3417
_diffrn_reflns_theta_full        69.84
_diffrn_reflns_theta_max         69.84
_diffrn_reflns_theta_min         3.26
_diffrn_standards_decay_%        3
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.075
_exptl_absorpt_correction_T_max  0.882
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(CORINC; Dräger & Gattow, 1971)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.202
_refine_ls_abs_structure_details 'Flack, (1983), 1270 Friedel pairs'
_refine_ls_abs_structure_Flack   -0.22(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0473
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0989P)²+0.3414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.1255
_refine_ls_wR_factor_ref         0.1267
_reflns_number_gt                2924
_reflns_number_total             3010
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            im2261.cif
_cod_data_source_block           I
_cod_database_code               2229410
_cod_database_fobs_code          2229410
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, 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_disorder_assembly
_atom_site_disorder_group
O O1 0.58864(5) 0.24963(11) 0.3890(3) 0.0240(3) Uani d . 1 . .
C C2 0.56177(7) 0.30020(15) 0.5965(4) 0.0215(4) Uani d . 1 . .
C C3 0.51656(8) 0.25513(16) 0.6587(5) 0.0242(4) Uani d . 1 . .
H H3 0.5068 0.1947 0.5587 0.029 Uiso calc R 1 . .
C C4 0.48548(8) 0.29789(17) 0.8665(5) 0.0245(4) Uani d . 1 . .
C C5 0.50161(8) 0.38484(16) 1.0212(5) 0.0242(4) Uani d . 1 . .
H H5 0.4818 0.4123 1.1728 0.029 Uiso calc R 1 . .
C C6 0.54556(8) 0.42947(15) 0.9536(5) 0.0234(4) Uani d . 1 . .
H H6 0.5556 0.4882 1.0605 0.028 Uiso calc R 1 . .
C C7 0.57698(7) 0.39218(15) 0.7306(4) 0.0216(4) Uani d . 1 . .
C C8 0.61655(7) 0.46277(15) 0.6377(4) 0.0222(4) Uani d . 1 . .
C C9 0.65513(7) 0.43587(15) 0.4150(5) 0.0215(4) Uani d . 1 . .
C C10 0.68194(8) 0.51865(17) 0.3032(5) 0.0248(4) Uani d . 1 . .
H H10 0.6752 0.5865 0.3670 0.030 Uiso calc R 1 . .
C C11 0.71823(7) 0.50081(16) 0.0997(5) 0.0262(5) Uani d . 1 . .
C C12 0.73012(8) 0.40368(18) 0.0000(5) 0.0275(5) Uani d . 1 . .
H H12 0.7551 0.3936 -0.1423 0.033 Uiso calc R 1 . .
C C13 0.70420(7) 0.32175(17) 0.1161(5) 0.0253(5) Uani d . 1 . .
H H13 0.7120 0.2541 0.0550 0.030 Uiso calc R 1 . .
C C14 0.66696(7) 0.33663(16) 0.3204(5) 0.0223(4) Uani d . 1 . .
C C15 0.64067(7) 0.24498(15) 0.4420(5) 0.0253(5) Uani d . 1 . .
H H15A 0.6542 0.1820 0.3525 0.030 Uiso calc R 1 . .
H H15B 0.6466 0.2412 0.6541 0.030 Uiso calc R 1 . .
N N16 0.43947(7) 0.25975(16) 0.9317(5) 0.0341(5) Uani d . 1 . .
H H16 0.4191 0.3040 1.0435 0.041 Uiso d R 1 . .
C C17 0.41597(8) 0.18098(18) 0.7713(5) 0.0287(5) Uani d . 1 . .
C C18 0.37502(8) 0.20134(19) 0.5998(6) 0.0352(5) Uani d . 1 . .
H H18 0.3631 0.2697 0.5860 0.042 Uiso calc R 1 . .
C C19 0.35112(10) 0.1240(2) 0.4481(7) 0.0434(6) Uani d . 1 . .
H H19 0.3226 0.1381 0.3345 0.052 Uiso calc R 1 . .
C C20 0.36991(10) 0.0266(2) 0.4670(6) 0.0407(6) Uani d . 1 . .
C C21 0.41046(10) 0.00166(19) 0.6308(7) 0.0409(6) Uani d . 1 . .
H H21 0.4229 -0.0664 0.6384 0.049 Uiso calc R 1 . .
C C22 0.43238(9) 0.0805(2) 0.7842(6) 0.0355(6) Uani d . 1 . .
F F23 0.34769(7) -0.04940(15) 0.3148(5) 0.0629(6) Uani d . 1 . .
F F24 0.47133(6) 0.05902(13) 0.9539(5) 0.0558(5) Uani d . 1 . .
O O25 0.61751(6) 0.55042(11) 0.7364(4) 0.0302(4) Uani d . 1 . .
N N26 0.74461(7) 0.58919(15) -0.0221(5) 0.0315(4) Uani d . 1 . .
O O27 0.73855(7) 0.67347(14) 0.0898(5) 0.0476(5) Uani d . 1 . .
O O28 0.77170(7) 0.57374(15) -0.2321(5) 0.0434(5) Uani d . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
C2 O1 C15 . . 115.13(16) ?
O1 C2 C3 . . 114.11(19) ?
O1 C2 C7 . . 123.99(18) ?
C3 C2 C7 . . 121.85(19) ?
C2 C3 C4 . . 120.4(2) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
N16 C4 C3 . . 123.6(2) ?
N16 C4 C5 . . 117.53(19) ?
C3 C4 C5 . . 118.85(19) ?
C6 C5 C4 . . 120.02(19) ?
C6 C5 H5 . . 120.0 ?
C4 C5 H5 . . 120.0 ?
C5 C6 C7 . . 122.89(19) ?
C5 C6 H6 . . 118.6 ?
C7 C6 H6 . . 118.6 ?
C2 C7 C6 . . 115.63(18) ?
C2 C7 C8 . . 128.01(18) ?
C6 C7 C8 . . 115.54(18) ?
O25 C8 C7 . . 119.20(19) ?
O25 C8 C9 . . 116.95(18) ?
C7 C8 C9 . . 123.78(18) ?
C10 C9 C14 . . 118.6(2) ?
C10 C9 C8 . . 115.52(18) ?
C14 C9 C8 . . 125.81(18) ?
C11 C10 C9 . . 119.3(2) ?
C11 C10 H10 . . 120.3 ?
C9 C10 H10 . . 120.3 ?
C10 C11 C12 . . 123.1(2) ?
C10 C11 N26 . . 118.3(2) ?
C12 C11 N26 . . 118.6(2) ?
C11 C12 C13 . . 117.4(2) ?
C11 C12 H12 . . 121.3 ?
C13 C12 H12 . . 121.3 ?
C12 C13 C14 . . 121.3(2) ?
C12 C13 H13 . . 119.3 ?
C14 C13 H13 . . 119.3 ?
C13 C14 C9 . . 120.24(19) ?
C13 C14 C15 . . 119.00(19) ?
C9 C14 C15 . . 120.75(19) ?
O1 C15 C14 . . 111.72(16) ?
O1 C15 H15A . . 109.3 ?
C14 C15 H15A . . 109.3 ?
O1 C15 H15B . . 109.3 ?
C14 C15 H15B . . 109.3 ?
H15A C15 H15B . . 107.9 ?
C4 N16 C17 . . 123.8(2) ?
C4 N16 H16 . . 115.2 ?
C17 N16 H16 . . 117.5 ?
C18 C17 C22 . . 117.5(2) ?
C18 C17 N16 . . 121.1(2) ?
C22 C17 N16 . . 121.3(2) ?
C17 C18 C19 . . 121.4(2) ?
C17 C18 H18 . . 119.3 ?
C19 C18 H18 . . 119.3 ?
C20 C19 C18 . . 117.9(2) ?
C20 C19 H19 . . 121.0 ?
C18 C19 H19 . . 121.0 ?
F23 C20 C19 . . 118.7(3) ?
F23 C20 C21 . . 117.8(3) ?
C19 C20 C21 . . 123.5(2) ?
C20 C21 C22 . . 116.6(2) ?
C20 C21 H21 . . 121.7 ?
C22 C21 H21 . . 121.7 ?
F24 C22 C21 . . 118.7(2) ?
F24 C22 C17 . . 118.3(2) ?
C21 C22 C17 . . 123.0(2) ?
O27 N26 O28 . . 123.8(2) ?
O27 N26 C11 . . 118.7(2) ?
O28 N26 C11 . . 117.5(2) ?
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
O1 C2 . 1.370(2) ?
O1 C15 . 1.431(3) ?
C2 C3 . 1.388(3) ?
C2 C7 . 1.410(3) ?
C3 C4 . 1.390(3) ?
C3 H3 . 0.9500 ?
C4 N16 . 1.375(3) ?
C4 C5 . 1.408(3) ?
C5 C6 . 1.361(3) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.419(3) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.476(3) ?
C8 O25 . 1.230(3) ?
C8 C9 . 1.504(3) ?
C9 C10 . 1.399(3) ?
C9 C14 . 1.403(3) ?
C10 C11 . 1.377(3) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.385(3) ?
C11 N26 . 1.467(3) ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.392(3) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.499(3) ?
C15 H15A . 0.9900 ?
C15 H15B . 0.9900 ?
N16 C17 . 1.416(3) ?
N16 H16 . 0.9504 ?
C17 C18 . 1.387(3) ?
C17 C22 . 1.385(3) ?
C18 C19 . 1.387(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.371(4) ?
C19 H19 . 0.9500 ?
C20 F23 . 1.355(3) ?
C20 C21 . 1.371(4) ?
C21 C22 . 1.381(4) ?
C21 H21 . 0.9500 ?
C22 F24 . 1.341(3) ?
N26 O27 . 1.225(3) ?
N26 O28 . 1.230(3) ?
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
N16 H16 O25 2_665 0.95 2.32 3.236(3) 162
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
C15 O1 C2 C3 . . . . -140.97(18) ?
C15 O1 C2 C7 . . . . 41.3(3) ?
O1 C2 C3 C4 . . . . 179.62(18) ?
C7 C2 C3 C4 . . . . -2.6(3) ?
C2 C3 C4 N16 . . . . 177.5(2) ?
C2 C3 C4 C5 . . . . -2.8(3) ?
N16 C4 C5 C6 . . . . -176.1(2) ?
C3 C4 C5 C6 . . . . 4.2(3) ?
C4 C5 C6 C7 . . . . -0.2(3) ?
O1 C2 C7 C6 . . . . -176.19(18) ?
C3 C2 C7 C6 . . . . 6.3(3) ?
O1 C2 C7 C8 . . . . 14.7(3) ?
C3 C2 C7 C8 . . . . -162.8(2) ?
C5 C6 C7 C2 . . . . -4.9(3) ?
C5 C6 C7 C8 . . . . 165.57(19) ?
C2 C7 C8 O25 . . . . 162.9(2) ?
C6 C7 C8 O25 . . . . -6.2(3) ?
C2 C7 C8 C9 . . . . -14.0(3) ?
C6 C7 C8 C9 . . . . 176.95(17) ?
O25 C8 C9 C10 . . . . -11.8(3) ?
C7 C8 C9 C10 . . . . 165.16(18) ?
O25 C8 C9 C14 . . . . 166.2(2) ?
C7 C8 C9 C14 . . . . -16.9(3) ?
C14 C9 C10 C11 . . . . 1.4(3) ?
C8 C9 C10 C11 . . . . 179.54(17) ?
C9 C10 C11 C12 . . . . -0.6(3) ?
C9 C10 C11 N26 . . . . 177.82(18) ?
C10 C11 C12 C13 . . . . -0.8(3) ?
N26 C11 C12 C13 . . . . -179.2(2) ?
C11 C12 C13 C14 . . . . 1.3(3) ?
C12 C13 C14 C9 . . . . -0.5(3) ?
C12 C13 C14 C15 . . . . -179.1(2) ?
C10 C9 C14 C13 . . . . -0.9(3) ?
C8 C9 C14 C13 . . . . -178.83(19) ?
C10 C9 C14 C15 . . . . 177.64(19) ?
C8 C9 C14 C15 . . . . -0.3(3) ?
C2 O1 C15 C14 . . . . -88.1(2) ?
C13 C14 C15 O1 . . . . -121.5(2) ?
C9 C14 C15 O1 . . . . 59.9(3) ?
C3 C4 N16 C17 . . . . -8.2(4) ?
C5 C4 N16 C17 . . . . 172.1(2) ?
C4 N16 C17 C18 . . . . -110.1(3) ?
C4 N16 C17 C22 . . . . 71.2(3) ?
C22 C17 C18 C19 . . . . 0.4(4) ?
N16 C17 C18 C19 . . . . -178.4(2) ?
C17 C18 C19 C20 . . . . -1.5(4) ?
C18 C19 C20 F23 . . . . -178.5(2) ?
C18 C19 C20 C21 . . . . 1.0(4) ?
F23 C20 C21 C22 . . . . -179.9(2) ?
C19 C20 C21 C22 . . . . 0.6(4) ?
C20 C21 C22 F24 . . . . 178.1(2) ?
C20 C21 C22 C17 . . . . -1.8(4) ?
C18 C17 C22 F24 . . . . -178.6(2) ?
N16 C17 C22 F24 . . . . 0.1(3) ?
C18 C17 C22 C21 . . . . 1.3(4) ?
N16 C17 C22 C21 . . . . -179.9(2) ?
C10 C11 N26 O27 . . . . 10.3(3) ?
C12 C11 N26 O27 . . . . -171.3(2) ?
C10 C11 N26 O28 . . . . -169.8(2) ?
C12 C11 N26 O28 . . . . 8.7(3) ?
