#------------------------------------------------------------------------------
#$Date: 2016-07-01 13:49:42 +0300 (Fri, 01 Jul 2016) $
#$Revision: 184112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/90/7119072.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_7119072
loop_
_publ_author_name
'Rong-Guo Shi'
'Xiao-Hua Wang'
'Ruzhang Liu'
'Chao-Guo Yan'
_publ_section_title
;
 Two-carbon ring expansion of isatin: a convenient construction of a
 dibenzo[b,d]azepinone scaffold
;
_journal_name_full               Chem.Commun.
_journal_page_first              6280
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C25 H14 F N O4'
_chemical_formula_sum            'C25 H14 F N O4'
_chemical_formula_weight         411.37
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1kkpvn
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.6330(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7639(11)
_cell_length_b                   19.413(2)
_cell_length_c                   10.4751(12)
_cell_measurement_reflns_used    6660
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.28
_cell_volume                     1912.1(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      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  '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  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16394
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0414
_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)+(0.0494P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1107
_reflns_number_gt                3537
_reflns_number_total             4405
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc00525j2.cif
_cod_data_source_block           1c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7119072
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_assembly
_atom_site_disorder_group
C1 C 0.49452(17) 0.95050(8) 0.21695(16) 0.0527(4) Uani 1 1 d . . .
H1A H 0.5303 0.9671 0.3027 0.063 Uiso 1 1 calc R . .
C2 C 0.58663(18) 0.92972(9) 0.14546(19) 0.0614(4) Uani 1 1 d . . .
H2 H 0.6843 0.9328 0.1827 0.074 Uiso 1 1 calc R . .
C3 C 0.53435(19) 0.90438(9) 0.01899(19) 0.0615(4) Uani 1 1 d . . .
H3 H 0.5967 0.8906 -0.0294 0.074 Uiso 1 1 calc R . .
C4 C 0.38890(19) 0.89938(9) -0.03622(17) 0.0574(4) Uani 1 1 d . . .
H4 H 0.3539 0.8815 -0.1212 0.069 Uiso 1 1 calc R . .
C5 C 0.29551(16) 0.92075(8) 0.03421(14) 0.0472(3) Uani 1 1 d . . .
H5 H 0.1979 0.9177 -0.0035 0.057 Uiso 1 1 calc R . .
C6 C 0.34788(15) 0.94672(7) 0.16139(13) 0.0409(3) Uani 1 1 d . . .
C7 C 0.25405(16) 0.97408(7) 0.24009(14) 0.0433(3) Uani 1 1 d . . .
C8 C 0.04178(15) 0.96778(7) 0.32833(13) 0.0384(3) Uani 1 1 d . . .
C9 C 0.09839(14) 0.94983(6) 0.21054(12) 0.0364(3) Uani 1 1 d . . .
H9 H 0.0437 0.9770 0.1351 0.044 Uiso 1 1 calc R . .
C10 C 0.06419(13) 0.87501(6) 0.17688(12) 0.0327(3) Uani 1 1 d . . .
C11 C 0.12450(13) 0.82333(6) 0.25977(12) 0.0336(3) Uani 1 1 d . . .
C12 C 0.23488(14) 0.83647(7) 0.38504(12) 0.0358(3) Uani 1 1 d . . .
C13 C 0.35556(15) 0.79379(8) 0.42241(14) 0.0434(3) Uani 1 1 d . . .
H13 H 0.3680 0.7582 0.3672 0.052 Uiso 1 1 calc R . .
C14 C 0.45446(16) 0.80523(8) 0.54080(16) 0.0502(4) Uani 1 1 d . . .
C15 C 0.44033(18) 0.85683(10) 0.62662(16) 0.0592(4) Uani 1 1 d . . .
H15 H 0.5086 0.8631 0.7069 0.071 Uiso 1 1 calc R . .
C16 C 0.32297(18) 0.89888(9) 0.59080(15) 0.0531(4) Uani 1 1 d . . .
H16 H 0.3116 0.9338 0.6479 0.064 Uiso 1 1 calc R . .
C17 C 0.22088(14) 0.89004(7) 0.47021(12) 0.0387(3) Uani 1 1 d . . .
C18 C -0.04769(14) 0.86130(7) 0.05005(12) 0.0364(3) Uani 1 1 d . . .
C19 C -0.09342(13) 0.78929(7) 0.01761(12) 0.0360(3) Uani 1 1 d . . .
C20 C -0.19452(16) 0.77432(8) -0.10126(14) 0.0475(3) Uani 1 1 d . . .
H20 H -0.2299 0.8092 -0.1621 0.057 Uiso 1 1 calc R . .
C21 C -0.24189(19) 0.70728(9) -0.12813(17) 0.0609(5) Uani 1 1 d . . .
H21 H -0.3082 0.6970 -0.2078 0.073 Uiso 1 1 calc R . .
C22 C -0.1911(2) 0.65547(9) -0.03715(18) 0.0629(5) Uani 1 1 d . . .
H22 H -0.2259 0.6109 -0.0549 0.075 Uiso 1 1 calc R . .
C23 C -0.08904(17) 0.66932(8) 0.07992(16) 0.0504(4) Uani 1 1 d . . .
H23 H -0.0544 0.6342 0.1403 0.060 Uiso 1 1 calc R . .
C24 C -0.03833(14) 0.73633(7) 0.10681(13) 0.0373(3) Uani 1 1 d . . .
C25 C 0.07458(14) 0.75023(7) 0.23088(13) 0.0384(3) Uani 1 1 d . . .
F1 F 0.57021(10) 0.76349(6) 0.57586(10) 0.0710(3) Uani 1 1 d . . .
N1 N 0.10335(13) 0.93506(6) 0.44330(11) 0.0407(3) Uani 1 1 d . . .
H1 H 0.0664 0.9426 0.5078 0.049 Uiso 1 1 calc R . .
O1 O 0.29529(14) 1.01756(6) 0.32484(12) 0.0668(4) Uani 1 1 d . . .
O2 O -0.05577(12) 1.00910(5) 0.31919(10) 0.0508(3) Uani 1 1 d . . .
O3 O -0.09957(12) 0.90903(5) -0.02298(11) 0.0569(3) Uani 1 1 d . . .
O4 O 0.12228(13) 0.70440(5) 0.30926(12) 0.0631(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
C2 C1 C6 120.35(16) . .
C2 C1 H1A 119.8 . .
C6 C1 H1A 119.8 . .
C3 C2 C1 120.08(16) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C2 C3 C4 119.98(16) . .
C2 C3 H3 120.0 . .
C4 C3 H3 120.0 . .
C5 C4 C3 120.39(16) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
C4 C5 C6 119.76(15) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C1 119.43(14) . .
C5 C6 C7 122.69(13) . .
C1 C6 C7 117.83(13) . .
O1 C7 C6 121.48(14) . .
O1 C7 C9 118.35(13) . .
C6 C7 C9 120.11(12) . .
O2 C8 N1 121.71(12) . .
O2 C8 C9 121.96(12) . .
N1 C8 C9 116.33(11) . .
C10 C9 C8 107.67(10) . .
C10 C9 C7 119.00(11) . .
C8 C9 C7 108.73(11) . .
C10 C9 H9 107.0 . .
C8 C9 H9 107.0 . .
C7 C9 H9 107.0 . .
C11 C10 C18 121.61(11) . .
C11 C10 C9 122.17(11) . .
C18 C10 C9 116.10(11) . .
C10 C11 C12 121.91(11) . .
C10 C11 C25 120.58(11) . .
C12 C11 C25 117.41(11) . .
C17 C12 C13 118.57(12) . .
C17 C12 C11 121.36(12) . .
C13 C12 C11 120.06(12) . .
C14 C13 C12 119.33(13) . .
C14 C13 H13 120.3 . .
C12 C13 H13 120.3 . .
F1 C14 C13 118.72(14) . .
F1 C14 C15 118.66(13) . .
C13 C14 C15 122.61(14) . .
C16 C15 C14 118.46(14) . .
C16 C15 H15 120.8 . .
C14 C15 H15 120.8 . .
C15 C16 C17 120.98(14) . .
C15 C16 H16 119.5 . .
C17 C16 H16 119.5 . .
C16 C17 C12 120.02(13) . .
C16 C17 N1 116.76(12) . .
C12 C17 N1 123.16(12) . .
O3 C18 C19 121.64(12) . .
O3 C18 C10 120.05(12) . .
C19 C18 C10 118.31(11) . .
C20 C19 C24 119.76(13) . .
C20 C19 C18 119.94(12) . .
C24 C19 C18 120.29(11) . .
C21 C20 C19 119.63(14) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C22 C21 C20 120.38(14) . .
C22 C21 H21 119.8 . .
C20 C21 H21 119.8 . .
C23 C22 C21 120.59(15) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C22 C23 C24 119.53(15) . .
C22 C23 H23 120.2 . .
C24 C23 H23 120.2 . .
C23 C24 C19 120.03(12) . .
C23 C24 C25 119.08(12) . .
C19 C24 C25 120.89(11) . .
O4 C25 C24 121.16(12) . .
O4 C25 C11 120.68(12) . .
C24 C25 C11 118.12(11) . .
C8 N1 C17 127.78(11) . .
C8 N1 H1 116.1 . .
C17 N1 H1 116.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.377(2) .
C1 C6 1.395(2) .
C1 H1A 0.9300 .
C2 C3 1.376(3) .
C2 H2 0.9300 .
C3 C4 1.385(3) .
C3 H3 0.9300 .
C4 C5 1.382(2) .
C4 H4 0.9300 .
C5 C6 1.387(2) .
C5 H5 0.9300 .
C6 C7 1.486(2) .
C7 O1 1.2125(17) .
C7 C9 1.541(2) .
C8 O2 1.2291(16) .
C8 N1 1.3509(17) .
C8 C9 1.5222(18) .
C9 C10 1.5106(17) .
C9 H9 0.9800 .
C10 C11 1.3534(17) .
C10 C18 1.4990(17) .
C11 C12 1.4786(17) .
C11 C25 1.5045(18) .
C12 C17 1.4008(18) .
C12 C13 1.4069(19) .
C13 C14 1.369(2) .
C13 H13 0.9300 .
C14 F1 1.3583(17) .
C14 C15 1.377(2) .
C15 C16 1.374(2) .
C15 H15 0.9300 .
C16 C17 1.3929(19) .
C16 H16 0.9300 .
C17 N1 1.4091(17) .
C18 O3 1.2212(16) .
C18 C19 1.4791(18) .
C19 C20 1.3953(18) .
C19 C24 1.3958(18) .
C20 C21 1.385(2) .
C20 H20 0.9300 .
C21 C22 1.382(3) .
C21 H21 0.9300 .
C22 C23 1.382(2) .
C22 H22 0.9300 .
C23 C24 1.3934(19) .
C23 H23 0.9300 .
C24 C25 1.4849(18) .
C25 O4 1.2150(16) .
N1 H1 0.8600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.07 2.8642(15) 153.7 3_576
