#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/99/2229994.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_2229994
loop_
_publ_author_name
'Yang, Kun'
'Li, Pei-Fan'
'Liu, Yan'
'Fang, Zhi-Zhong'
_publ_section_title
;
 1-(2-Chlorophenyl)-6-fluoro-2-methyl-1H-indole-3-carbonitrile
;
_journal_coeditor_code           HB5823
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1041
_journal_paper_doi               10.1107/S1600536811011214
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C16 H10 Cl F N2'
_chemical_formula_moiety         'C16 H10 Cl F N2'
_chemical_formula_sum            'C16 H10 Cl F N2'
_chemical_formula_weight         284.71
_chemical_name_systematic
;
1-(2-Chlorophenyl)-6-fluoro-2-methyl-1H-indole-3-carbonitrile
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.4581(9)
_cell_length_b                   16.8480(15)
_cell_length_c                   21.356(2)
_cell_measurement_reflns_used    10281
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      31.40
_cell_measurement_theta_min      1.50
_cell_volume                     2683.5(5)
_computing_cell_refinement       'CrystalClear (Rigaku, 2009)'
_computing_data_collection       'CrystalClear (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear (Rigaku, 2009)'
_computing_molecular_graphics    'CrystalStructure (Rigaku, 2009)'
_computing_publication_material  'CrystalStructure (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.222
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku Saturn724 CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  multilayer
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0252
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            28426
_diffrn_reflns_theta_full        30.03
_diffrn_reflns_theta_max         30.03
_diffrn_reflns_theta_min         1.91
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.9450
_exptl_absorpt_correction_T_min  0.9294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2009)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.199
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3893
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0407
_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)+(0.0644P)²+0.1004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                3219
_reflns_number_total             3893
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5823.cif
_cod_data_source_block           I
_cod_database_code               2229994
_cod_database_fobs_code          2229994
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, z'
'x, -y+1/2, z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, -z'
'-x, y-1/2, -z-1/2'
'x-1/2, y, -z-1/2'
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
Cl Cl1 0.50520(4) 0.220294(19) 0.641958(16) 0.03226(11) Uani d . 1 . .
F F1 0.61121(11) 0.54670(5) 0.76153(4) 0.0480(2) Uani d . 1 . .
N N1 0.39260(12) 0.37712(5) 0.59488(4) 0.0236(2) Uani d . 1 . .
N N2 0.79477(16) 0.43384(7) 0.42798(6) 0.0420(3) Uani d . 1 . .
C C1 0.45553(17) 0.36559(7) 0.53489(5) 0.0258(2) Uani d . 1 . .
C C2 0.60108(16) 0.41469(7) 0.52619(6) 0.0271(3) Uani d . 1 . .
C C3 0.63160(15) 0.45816(7) 0.58328(6) 0.0265(3) Uani d . 1 . .
C C4 0.49938(14) 0.43272(7) 0.62558(6) 0.0237(2) Uani d . 1 . .
C C5 0.48747(16) 0.46061(7) 0.68659(6) 0.0280(3) Uani d . 1 . .
H H5 0.3986 0.4427 0.7151 0.034 Uiso calc R 1 . .
C C6 0.61408(17) 0.51607(7) 0.70243(6) 0.0337(3) Uani d . 1 . .
C C7 0.74735(17) 0.54359(8) 0.66235(7) 0.0361(3) Uani d . 1 . .
H H7 0.8315 0.5819 0.6765 0.043 Uiso calc R 1 . .
C C8 0.75667(16) 0.51503(7) 0.60210(7) 0.0318(3) Uani d . 1 . .
H H8 0.8460 0.5336 0.5740 0.038 Uiso calc R 1 . .
C C9 0.36953(19) 0.30813(8) 0.49124(6) 0.0333(3) Uani d . 1 . .
H H9A 0.3812 0.2543 0.5081 0.040 Uiso calc R 1 . .
H H9B 0.4286 0.3109 0.4503 0.040 Uiso calc R 1 . .
H H9C 0.2423 0.3213 0.4866 0.040 Uiso calc R 1 . .
C C10 0.70533(17) 0.42350(7) 0.47083(6) 0.0317(3) Uani d . 1 . .
C C11 0.25337(16) 0.33290(7) 0.62467(5) 0.0223(2) Uani d . 1 . .
C C12 0.28935(15) 0.25756(7) 0.64802(5) 0.0230(2) Uani d . 1 . .
C C13 0.15588(16) 0.21330(7) 0.67690(5) 0.0271(3) Uani d . 1 . .
H H13 0.1800 0.1612 0.6918 0.032 Uiso calc R 1 . .
C C14 -0.01309(16) 0.24642(8) 0.68363(6) 0.0277(3) Uani d . 1 . .
H H14 -0.1052 0.2169 0.7037 0.033 Uiso calc R 1 . .
C C15 -0.04958(18) 0.32238(7) 0.66141(6) 0.0295(3) Uani d . 1 . .
H H15 -0.1658 0.3446 0.6664 0.035 Uiso calc R 1 . .
C C16 0.08411(16) 0.36557(7) 0.63194(6) 0.0276(3) Uani d . 1 . .
H H16 0.0598 0.4175 0.6167 0.033 Uiso calc R 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
C1 N1 C4 . . 109.73(9) ?
C1 N1 C11 . . 126.05(10) ?
C4 N1 C11 . . 123.83(9) ?
C2 C1 N1 . . 108.01(10) ?
C2 C1 C9 . . 130.19(11) ?
N1 C1 C9 . . 121.80(11) ?
C1 C2 C10 . . 127.27(12) ?
C1 C2 C3 . . 108.40(10) ?
C10 C2 C3 . . 124.33(11) ?
C8 C3 C4 . . 119.56(12) ?
C8 C3 C2 . . 134.28(11) ?
C4 C3 C2 . . 106.16(10) ?
C5 C4 N1 . . 129.26(11) ?
C5 C4 C3 . . 123.06(11) ?
N1 C4 C3 . . 107.68(11) ?
C6 C5 C4 . . 114.73(11) ?
C6 C5 H5 . . 122.6 ?
C4 C5 H5 . . 122.6 ?
F1 C6 C5 . . 118.39(12) ?
F1 C6 C7 . . 117.04(11) ?
C5 C6 C7 . . 124.57(13) ?
C8 C7 C6 . . 119.68(12) ?
C8 C7 H7 . . 120.2 ?
C6 C7 H7 . . 120.2 ?
C7 C8 C3 . . 118.39(12) ?
C7 C8 H8 . . 120.8 ?
C3 C8 H8 . . 120.8 ?
C1 C9 H9A . . 109.5 ?
C1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
C1 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N2 C10 C2 . . 176.12(15) ?
C16 C11 C12 . . 119.89(10) ?
C16 C11 N1 . . 120.35(10) ?
C12 C11 N1 . . 119.73(10) ?
C13 C12 C11 . . 120.76(11) ?
C13 C12 Cl1 . . 120.31(9) ?
C11 C12 Cl1 . . 118.91(9) ?
C14 C13 C12 . . 118.81(11) ?
C14 C13 H13 . . 120.6 ?
C12 C13 H13 . . 120.6 ?
C13 C14 C15 . . 120.85(11) ?
C13 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C16 C15 C14 . . 119.80(12) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C15 C16 C11 . . 119.86(11) ?
C15 C16 H16 . . 120.1 ?
C11 C16 H16 . . 120.1 ?
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
Cl1 C12 . 1.7328(12) ?
F1 C6 . 1.3636(15) ?
N1 C1 . 1.3780(15) ?
N1 C4 . 1.3934(14) ?
N1 C11 . 1.4276(14) ?
N2 C10 . 1.1457(16) ?
C1 C2 . 1.3775(16) ?
C1 C9 . 1.4892(17) ?
C2 C10 . 1.4227(17) ?
C2 C3 . 1.4404(18) ?
C3 C8 . 1.3963(17) ?
C3 C4 . 1.4045(16) ?
C4 C5 . 1.3879(18) ?
C5 C6 . 1.3708(17) ?
C5 H5 . 0.9500 ?
C6 C7 . 1.3914(19) ?
C7 C8 . 1.375(2) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 H9A . 0.9800 ?
C9 H9B . 0.9800 ?
C9 H9C . 0.9800 ?
C11 C16 . 1.3857(16) ?
C11 C12 . 1.3900(15) ?
C12 C13 . 1.3883(16) ?
C13 C14 . 1.3857(17) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3918(18) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3855(17) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
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
C7 H7 F1 8_657 0.95 2.54 3.1638(16) 123
C7 H7 Cl1 2_655 0.95 2.73 3.5296(14) 142
C15 H15 Cg1 1_455 0.95 2.92 3.7246(14) 143
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
C4 N1 C1 C2 . . . . -1.08(13) ?
C11 N1 C1 C2 . . . . -174.11(10) ?
C4 N1 C1 C9 . . . . 178.91(11) ?
C11 N1 C1 C9 . . . . 5.89(17) ?
N1 C1 C2 C10 . . . . -178.61(11) ?
C9 C1 C2 C10 . . . . 1.4(2) ?
N1 C1 C2 C3 . . . . 0.59(13) ?
C9 C1 C2 C3 . . . . -179.40(12) ?
C1 C2 C3 C8 . . . . 179.90(13) ?
C10 C2 C3 C8 . . . . -0.9(2) ?
C1 C2 C3 C4 . . . . 0.10(13) ?
C10 C2 C3 C4 . . . . 179.33(11) ?
C1 N1 C4 C5 . . . . -178.37(12) ?
C11 N1 C4 C5 . . . . -5.16(18) ?
C1 N1 C4 C3 . . . . 1.15(13) ?
C11 N1 C4 C3 . . . . 174.36(10) ?
C8 C3 C4 C5 . . . . -1.03(17) ?
C2 C3 C4 C5 . . . . 178.81(11) ?
C8 C3 C4 N1 . . . . 179.41(10) ?
C2 C3 C4 N1 . . . . -0.75(12) ?
N1 C4 C5 C6 . . . . -179.77(11) ?
C3 C4 C5 C6 . . . . 0.78(17) ?
C4 C5 C6 F1 . . . . 179.77(11) ?
C4 C5 C6 C7 . . . . -0.48(18) ?
F1 C6 C7 C8 . . . . -179.81(11) ?
C5 C6 C7 C8 . . . . 0.4(2) ?
C6 C7 C8 C3 . . . . -0.63(18) ?
C4 C3 C8 C7 . . . . 0.91(17) ?
C2 C3 C8 C7 . . . . -178.87(13) ?
C1 C2 C10 N2 . . . . 18E1(10) ?
C3 C2 C10 N2 . . . . -2(2) ?
C1 N1 C11 C16 . . . . -104.36(13) ?
C4 N1 C11 C16 . . . . 83.56(14) ?
C1 N1 C11 C12 . . . . 77.42(15) ?
C4 N1 C11 C12 . . . . -94.66(13) ?
C16 C11 C12 C13 . . . . 2.09(17) ?
N1 C11 C12 C13 . . . . -179.69(10) ?
C16 C11 C12 Cl1 . . . . -176.62(9) ?
N1 C11 C12 Cl1 . . . . 1.61(15) ?
C11 C12 C13 C14 . . . . -1.76(17) ?
Cl1 C12 C13 C14 . . . . 176.93(9) ?
C12 C13 C14 C15 . . . . 0.59(18) ?
C13 C14 C15 C16 . . . . 0.24(19) ?
C14 C15 C16 C11 . . . . 0.07(19) ?
C12 C11 C16 C15 . . . . -1.22(17) ?
N1 C11 C16 C15 . . . . -179.44(11) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 28560635
