#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/20/2222054.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_2222054
loop_
_publ_author_name
'Zhang, Jinpeng'
'Ding, Jie'
'Yan, Shu'
'Rong, Liangce'
'Xu, Lichun'
_publ_section_title
4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-carbonitrile
_journal_coeditor_code           HK2684
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1354
_journal_paper_doi               10.1107/S1600536809017991
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C20 H13 F N2 O'
_chemical_formula_moiety         'C20 H13 F N2 O'
_chemical_formula_sum            'C20 H13 F N2 O'
_chemical_formula_weight         316.32
_chemical_melting_point_gt       598
_chemical_name_systematic
;
4-(4-Fluorophenyl)-2-oxo-1,2,5,6-tetrahydrobenzo[h]quinoline-3-
carbonitrile
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                98.674(19)
_cell_angle_beta                 105.095(17)
_cell_angle_gamma                104.846(18)
_cell_formula_units_Z            2
_cell_length_a                   8.116(10)
_cell_length_b                   9.278(12)
_cell_length_c                   11.263(14)
_cell_measurement_reflns_used    929
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.365
_cell_measurement_theta_min      2.335
_cell_volume                     769.7(17)
_computing_cell_refinement       'SAINT (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3950
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.34
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9563
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2656
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0482
_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)+(0.0683P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1436
_reflns_number_gt                1399
_reflns_number_total             2656
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2684.cif
_cod_data_source_block           I
_cod_original_cell_volume        769.7(16)
_cod_database_code               2222054
_cod_database_fobs_code          2222054
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
F F1 0.2899(2) 0.4261(2) -0.18711(16) 0.1127(7) Uani d . 1 A .
N N1 0.2029(3) 0.1315(2) 0.45914(18) 0.0580(6) Uani d . 1 A .
H H1 0.1926 0.0948 0.5235 0.070 Uiso calc R 1 . .
N N2 -0.2136(3) 0.1660(3) 0.0916(2) 0.0781(7) Uani d . 1 A .
O O1 -0.101(3) 0.0761(19) 0.3875(16) 0.063(2) Uani d P 0.489(17) A 1
O O1' -0.100(2) 0.0203(19) 0.3604(16) 0.063(2) Uani d P 0.511(17) A 2
C C1 0.0482(3) 0.1170(3) 0.3667(2) 0.0589(7) Uani d . 1 . .
C C2 0.0742(3) 0.1847(3) 0.2646(2) 0.0474(6) Uani d . 1 A .
C C3 0.2423(3) 0.2493(3) 0.2576(2) 0.0449(6) Uani d . 1 . .
C C4 0.3947(3) 0.2594(3) 0.3564(2) 0.0514(7) Uani d DU 1 A .
C C5 0.3716(3) 0.1991(3) 0.4576(2) 0.0441(6) Uani d . 1 . .
C C6 0.5250(3) 0.2014(3) 0.5626(2) 0.0472(6) Uani d . 1 A .
C C7 0.5053(4) 0.1393(3) 0.6645(2) 0.0611(7) Uani d . 1 . .
H H7 0.3908 0.0975 0.6694 0.073 Uiso calc R 1 A .
C C8 0.6514(4) 0.1387(3) 0.7579(2) 0.0673(8) Uani d . 1 A .
H H8 0.6354 0.0973 0.8259 0.081 Uiso calc R 1 . .
C C9 0.8191(4) 0.1978(3) 0.7521(3) 0.0705(8) Uani d . 1 . .
H H9 0.9181 0.1954 0.8149 0.085 Uiso calc R 1 A .
C C10 0.8420(4) 0.2613(4) 0.6529(3) 0.0817(9) Uani d . 1 A .
H H10 0.9575 0.3021 0.6496 0.098 Uiso calc R 1 . .
C C11 0.6977(4) 0.2660(3) 0.5580(2) 0.0652(8) Uani d DU 1 . .
C C12 0.7151(13) 0.2943(16) 0.4310(10) 0.060(2) Uani d PDU 0.435(13) A 1
H H12A 0.8345 0.3611 0.4429 0.072 Uiso calc PR 0.435(13) A 1
H H12B 0.6964 0.1979 0.3740 0.072 Uiso calc PR 0.435(13) A 1
C C13 0.5770(13) 0.3675(14) 0.3755(13) 0.061(3) Uani d PDU 0.435(13) A 1
H H13A 0.5955 0.4640 0.4323 0.073 Uiso calc PR 0.435(13) A 1
H H13B 0.5872 0.3880 0.2953 0.073 Uiso calc PR 0.435(13) A 1
C C12' 0.7237(10) 0.3759(13) 0.4687(7) 0.069(2) Uani d PDU 0.565(13) A 2
H H12C 0.7097 0.4729 0.5027 0.083 Uiso calc PR 0.565(13) A 2
H H12D 0.8432 0.3954 0.4608 0.083 Uiso calc PR 0.565(13) A 2
C C13' 0.5852(10) 0.3014(12) 0.3417(7) 0.059(2) Uani d PDU 0.565(13) A 2
H H13C 0.6068 0.2095 0.3046 0.071 Uiso calc PR 0.565(13) A 2
H H13D 0.5936 0.3710 0.2858 0.071 Uiso calc PR 0.565(13) A 2
C C14 0.2601(3) 0.3026(3) 0.1417(2) 0.0493(6) Uani d . 1 A .
C C15 0.2276(4) 0.4341(3) 0.1176(3) 0.0681(8) Uani d . 1 . .
H H15 0.1976 0.4956 0.1764 0.082 Uiso calc R 1 A .
C C16 0.2388(4) 0.4774(4) 0.0065(3) 0.0769(9) Uani d . 1 A .
H H16 0.2165 0.5671 -0.0098 0.092 Uiso calc R 1 . .
C C17 0.2827(4) 0.3865(4) -0.0771(3) 0.0729(9) Uani d . 1 . .
C C18 0.3162(4) 0.2565(4) -0.0566(3) 0.0858(10) Uani d . 1 A .
H H18 0.3456 0.1957 -0.1163 0.103 Uiso calc R 1 . .
C C19 0.3064(4) 0.2146(4) 0.0539(3) 0.0769(9) Uani d . 1 . .
H H19 0.3314 0.1256 0.0696 0.092 Uiso calc R 1 A .
C C20 -0.0853(4) 0.1739(3) 0.1674(2) 0.0561(7) 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 0.0033 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C1 . . 125.3(2) ?
C5 N1 H1 . . 117.4 ?
C1 N1 H1 . . 117.4 ?
O1 C1 N1 . . 119.7(9) ?
O1' C1 N1 . . 120.2(8) ?
O1 C1 C2 . . 124.0(9) ?
O1' C1 C2 . . 123.2(8) ?
N1 C1 C2 . . 114.7(2) ?
C3 C2 C1 . . 121.7(2) ?
C3 C2 C20 . . 122.2(2) ?
C1 C2 C20 . . 116.0(2) ?
C2 C3 C4 . . 120.1(2) ?
C2 C3 C14 . . 119.1(2) ?
C4 C3 C14 . . 120.8(2) ?
C5 C4 C3 . . 118.8(2) ?
C5 C4 C13 . . 116.3(5) ?
C3 C4 C13 . . 122.8(5) ?
C5 C4 C13' . . 118.0(4) ?
C3 C4 C13' . . 121.8(4) ?
N1 C5 C4 . . 119.4(2) ?
N1 C5 C6 . . 118.8(2) ?
C4 C5 C6 . . 121.8(2) ?
C7 C6 C11 . . 118.7(2) ?
C7 C6 C5 . . 122.9(2) ?
C11 C6 C5 . . 118.4(2) ?
C8 C7 C6 . . 121.1(3) ?
C8 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C9 C8 C7 . . 120.4(3) ?
C9 C8 H8 . . 119.8 ?
C7 C8 H8 . . 119.8 ?
C8 C9 C10 . . 119.5(3) ?
C8 C9 H9 . . 120.2 ?
C10 C9 H9 . . 120.2 ?
C9 C10 C11 . . 121.6(3) ?
C9 C10 H10 . . 119.2 ?
C11 C10 H10 . . 119.2 ?
C10 C11 C6 . . 118.7(3) ?
C10 C11 C12 . . 121.7(4) ?
C6 C11 C12 . . 117.1(4) ?
C10 C11 C12' . . 120.9(4) ?
C6 C11 C12' . . 118.5(4) ?
C13 C12 C11 . . 108.8(9) ?
C13 C12 H12A . . 109.9 ?
C11 C12 H12A . . 109.9 ?
C13 C12 H12B . . 109.9 ?
C11 C12 H12B . . 109.9 ?
H12A C12 H12B . . 108.3 ?
C4 C13 C12 . . 108.2(9) ?
C4 C13 H13A . . 110.1 ?
C12 C13 H13A . . 110.1 ?
C4 C13 H13B . . 110.1 ?
C12 C13 H13B . . 110.1 ?
H13A C13 H13B . . 108.4 ?
C13' C12' C11 . . 108.2(7) ?
C13' C12' H12C . . 110.1 ?
C11 C12' H12C . . 110.1 ?
C13' C12' H12D . . 110.1 ?
C11 C12' H12D . . 110.1 ?
H12C C12' H12D . . 108.4 ?
C12' C13' C4 . . 109.8(7) ?
C12' C13' H13C . . 109.7 ?
C4 C13' H13C . . 109.7 ?
C12' C13' H13D . . 109.7 ?
C4 C13' H13D . . 109.7 ?
H13C C13' H13D . . 108.2 ?
C15 C14 C19 . . 118.4(2) ?
C15 C14 C3 . . 122.3(2) ?
C19 C14 C3 . . 119.2(2) ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C17 C16 C15 . . 118.4(3) ?
C17 C16 H16 . . 120.8 ?
C15 C16 H16 . . 120.8 ?
C18 C17 C16 . . 122.5(3) ?
C18 C17 F1 . . 118.7(3) ?
C16 C17 F1 . . 118.8(3) ?
C17 C18 C19 . . 118.9(3) ?
C17 C18 H18 . . 120.5 ?
C19 C18 H18 . . 120.5 ?
C18 C19 C14 . . 120.9(3) ?
C18 C19 H19 . . 119.6 ?
C14 C19 H19 . . 119.6 ?
N2 C20 C2 . . 178.8(3) ?
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
F1 C17 . 1.356(3) ?
N1 C5 . 1.358(3) ?
N1 C1 . 1.367(3) ?
N1 H1 . 0.8600 ?
N2 C20 . 1.139(3) ?
O1 C1 . 1.267(18) ?
O1' C1 . 1.279(18) ?
C1 C2 . 1.428(3) ?
C2 C3 . 1.370(3) ?
C2 C20 . 1.431(4) ?
C3 C4 . 1.404(3) ?
C3 C14 . 1.491(3) ?
C4 C5 . 1.377(3) ?
C4 C13 . 1.499(10) ?
C4 C13' . 1.553(8) ?
C5 C6 . 1.470(3) ?
C6 C7 . 1.387(3) ?
C6 C11 . 1.394(4) ?
C7 C8 . 1.367(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.354(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.371(4) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.381(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.528(9) ?
C11 C12' . 1.550(8) ?
C12 C13 . 1.505(14) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C12' C13' . 1.501(12) ?
C12' H12C . 0.9700 ?
C12' H12D . 0.9700 ?
C13' H13C . 0.9700 ?
C13' H13D . 0.9700 ?
C14 C15 . 1.363(4) ?
C14 C19 . 1.376(4) ?
C15 C16 . 1.389(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.347(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.342(4) ?
C18 C19 . 1.375(4) ?
C18 H18 . 0.9300 ?
C19 H19 . 0.9300 ?
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
_geom_hbond_publ_flag
N1 H1 O1 2_556 0.86 2.08 2.883(3) 155 yes
C7 H7 O1 2_556 0.93 2.35 3.223(3) 157 yes
C12 H12B O1 1_655 0.97 2.21 2.863(3) 124 yes
C13 H13B F1 2_665 0.97 2.42 3.270(3) 147 yes
C15 H15 Cg3 2_666 0.93 2.90 3.671(3) 141 yes
