# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RT-SP-11A
_database_code_depnum_ccdc_archive 'CCDC 1487091'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H9 F N2'
_chemical_formula_moiety         'C15 H9 F N2'
_chemical_formula_weight         236.25
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   25.513(13)
_cell_length_b                   13.881(8)
_cell_length_c                   6.794(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2406(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2123
_cell_measurement_theta_min      4.49
_cell_measurement_theta_max      27.99
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.320
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976.00
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_T_max  0.972

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.849
_diffrn_reflns_number            20801
_diffrn_reflns_av_R_equivalents  0.1085
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2754
_reflns_number_gt                1690
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.1134
_refine_ls_wR_factor_ref         0.3222
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2754
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1402P)²+2.7382P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.106
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.470
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F 0.6249(2) 0.1661(5) 0.3592(10) 0.181(3) Uani 1.0 8 d . . .
N1 N 0.42301(12) 0.1030(3) 0.6720(5) 0.0497(9) Uani 1.0 8 d . . .
N2 N 0.39267(16) 0.0216(4) 0.9700(6) 0.0813(14) Uani 1.0 8 d . . .
C1 C 0.39167(15) 0.1332(3) 0.5145(6) 0.0490(10) Uani 1.0 8 d . . .
C2 C 0.42409(19) 0.1620(3) 0.3718(7) 0.0525(11) Uani 1.0 8 d . . .
C3 C 0.47694(15) 0.1502(3) 0.4327(6) 0.0494(10) Uani 1.0 8 d . . .
C4 C 0.5262(3) 0.1671(5) 0.3497(8) 0.0580(14) Uani 1.0 8 d . . .
C5 C 0.57130(16) 0.1458(3) 0.4486(7) 0.0589(11) Uani 1.0 8 d . . .
C6 C 0.56788(18) 0.1054(3) 0.6349(8) 0.0603(12) Uani 1.0 8 d . . .
C7 C 0.52041(17) 0.0878(3) 0.7243(8) 0.0567(11) Uani 1.0 8 d . . .
C8 C 0.47579(14) 0.1118(3) 0.6202(6) 0.0489(10) Uani 1.0 8 d . . .
C9 C 0.40636(16) 0.0592(3) 0.8323(6) 0.0567(11) Uani 1.0 8 d . . .
C10 C 0.33418(15) 0.1283(3) 0.5279(7) 0.0504(10) Uani 1.0 8 d . . .
C11 C 0.3056(3) 0.0909(4) 0.3747(9) 0.0637(14) Uani 1.0 8 d . . .
C12 C 0.2515(2) 0.0855(4) 0.3835(10) 0.0760(15) Uani 1.0 8 d . . .
C13 C 0.2252(2) 0.1191(4) 0.5440(10) 0.0754(15) Uani 1.0 8 d . . .
C14 C 0.2534(3) 0.1578(5) 0.6969(11) 0.0769(16) Uani 1.0 8 d . . .
C15 C 0.30736(17) 0.1620(4) 0.6898(8) 0.0632(12) Uani 1.0 8 d . . .
H2 H 0.4132(17) 0.188(3) 0.258(8) 0.064(14) Uani 1.0 8 d . . .
H4 H 0.5285(17) 0.191(4) 0.233(9) 0.072(18) Uani 1.0 8 d . . .
H6 H 0.6004(19) 0.087(3) 0.694(8) 0.077(15) Uani 1.0 8 d . . .
H7 H 0.5207(18) 0.057(3) 0.869(8) 0.076(15) Uani 1.0 8 d . . .
H11 H 0.3236(19) 0.071(4) 0.268(8) 0.073(17) Uani 1.0 8 d . . .
H12 H 0.2302(18) 0.057(4) 0.280(8) 0.086(17) Uani 1.0 8 d . . .
H13 H 0.1861(17) 0.118(4) 0.543(10) 0.12(3) Uani 1.0 8 d . . .
H14 H 0.237(3) 0.187(6) 0.809(13) 0.15(3) Uani 1.0 8 d . . .
H15 H 0.327(2) 0.188(4) 0.806(7) 0.093(18) Uani 1.0 8 d . . .



#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C5 1.523(7) yes . .
N1 C1 1.400(5) yes . .
N1 C8 1.397(5) yes . .
N1 C9 1.317(6) yes . .
N2 C9 1.128(6) yes . .
C1 C2 1.336(6) yes . .
C1 C10 1.471(6) yes . .
C2 C3 1.420(7) yes . .
C3 C4 1.397(8) yes . .
C3 C8 1.381(6) yes . .
C4 C5 1.365(8) yes . .
C5 C6 1.387(7) yes . .
C6 C7 1.377(7) yes . .
C7 C8 1.381(6) yes . .
C10 C11 1.373(7) yes . .
C10 C15 1.378(7) yes . .
C11 C12 1.383(8) yes . .
C12 C13 1.362(9) yes . .
C13 C14 1.372(9) yes . .
C14 C15 1.380(8) yes . .
C2 H2 0.90(5) no . .
C4 H4 0.86(6) no . .
C6 H6 0.96(5) no . .
C7 H7 1.07(5) no . .
C11 H11 0.90(5) no . .
C12 H12 0.97(6) no . .
C13 H13 1.00(5) no . .
C14 H14 0.96(8) no . .
C15 H15 1.00(5) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C8 109.4(3) yes . . .
C1 N1 C9 125.9(4) yes . . .
C8 N1 C9 124.0(4) yes . . .
N1 C1 C2 106.9(4) yes . . .
N1 C1 C10 120.6(4) yes . . .
C2 C1 C10 132.5(4) yes . . .
C1 C2 C3 110.0(4) yes . . .
C2 C3 C4 135.8(5) yes . . .
C2 C3 C8 107.1(4) yes . . .
C4 C3 C8 117.1(4) yes . . .
C3 C4 C5 121.5(5) yes . . .
F1 C5 C4 121.4(5) yes . . .
F1 C5 C6 119.7(5) yes . . .
C4 C5 C6 118.9(5) yes . . .
C5 C6 C7 122.0(5) yes . . .
C6 C7 C8 117.2(5) yes . . .
N1 C8 C3 106.7(4) yes . . .
N1 C8 C7 130.1(4) yes . . .
C3 C8 C7 123.2(4) yes . . .
N1 C9 N2 179.2(5) yes . . .
C1 C10 C11 120.0(4) yes . . .
C1 C10 C15 121.9(4) yes . . .
C11 C10 C15 118.0(4) yes . . .
C10 C11 C12 121.2(6) yes . . .
C11 C12 C13 120.5(6) yes . . .
C12 C13 C14 118.8(6) yes . . .
C13 C14 C15 120.8(6) yes . . .
C10 C15 C14 120.6(5) yes . . .
C1 C2 H2 124(3) no . . .
C3 C2 H2 126(3) no . . .
C3 C4 H4 120(3) no . . .
C5 C4 H4 119(3) no . . .
C5 C6 H6 116(3) no . . .
C7 C6 H6 122(3) no . . .
C6 C7 H7 118(3) no . . .
C8 C7 H7 125(3) no . . .
C10 C11 H11 117(3) no . . .
C12 C11 H11 122(3) no . . .
C11 C12 H12 123(3) no . . .
C13 C12 H12 116(3) no . . .
C12 C13 H13 119(4) no . . .
C14 C13 H13 122(4) no . . .
C13 C14 H14 122(4) no . . .
C15 C14 H14 117(4) no . . .
C10 C15 H15 121(3) no . . .
C14 C15 H15 119(3) no . . .

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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C8 C3 1.7(4) no . . . .
C1 N1 C8 C7 -177.5(4) no . . . .
C8 N1 C1 C2 -1.4(4) no . . . .
C8 N1 C1 C10 178.0(3) no . . . .
C9 N1 C1 C2 -171.8(4) no . . . .
C9 N1 C1 C10 7.6(6) no . . . .
C9 N1 C8 C3 172.3(4) no . . . .
C9 N1 C8 C7 -6.9(6) no . . . .
N1 C1 C2 C3 0.6(5) no . . . .
N1 C1 C10 C11 -133.7(4) no . . . .
N1 C1 C10 C15 47.5(5) no . . . .
C2 C1 C10 C11 45.6(6) no . . . .
C2 C1 C10 C15 -133.2(5) no . . . .
C10 C1 C2 C3 -178.7(4) no . . . .
C1 C2 C3 C4 180.0(4) no . . . .
C1 C2 C3 C8 0.4(5) no . . . .
C2 C3 C4 C5 -178.9(4) no . . . .
C2 C3 C8 N1 -1.3(4) no . . . .
C2 C3 C8 C7 178.0(3) no . . . .
C4 C3 C8 N1 179.1(4) no . . . .
C4 C3 C8 C7 -1.7(6) no . . . .
C8 C3 C4 C5 0.6(7) no . . . .
C3 C4 C5 F1 -178.8(4) no . . . .
C3 C4 C5 C6 0.8(7) no . . . .
F1 C5 C6 C7 178.3(4) no . . . .
C4 C5 C6 C7 -1.3(7) no . . . .
C5 C6 C7 C8 0.3(7) no . . . .
C6 C7 C8 N1 -179.7(4) no . . . .
C6 C7 C8 C3 1.2(6) no . . . .
C1 C10 C11 C12 -180.0(4) no . . . .
C1 C10 C15 C14 179.0(4) no . . . .
C11 C10 C15 C14 0.2(6) no . . . .
C15 C10 C11 C12 -1.1(7) no . . . .
C10 C11 C12 C13 1.2(8) no . . . .
C11 C12 C13 C14 -0.4(8) no . . . .
C12 C13 C14 C15 -0.5(9) no . . . .
C13 C14 C15 C10 0.6(8) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C4 3.538(7) no . .
N1 C15 3.065(6) no . .
N2 C1 3.461(6) no . .
N2 C8 3.423(6) no . .
N2 C15 3.487(7) no . .
C2 C7 3.583(7) no . .
C2 C9 3.468(7) no . .
C2 C11 3.180(8) no . .
C3 C6 2.767(7) no . .
C3 C9 3.494(6) no . .
C4 C7 2.777(8) no . .
C5 C8 2.742(6) no . .
C7 C9 3.027(7) no . .
C9 C10 2.930(6) no . .
C9 C15 3.058(7) no . .
C10 C13 2.785(7) no . .
C11 C14 2.726(9) no . .
C12 C15 2.736(8) no . .
F1 N2 3.463(8) no . 5_656
F1 C9 3.481(8) no . 5_656
N1 C2 3.534(6) no . 3_555
N1 C5 3.552(6) no . 5_656
N1 C6 3.572(6) no . 5_656
N2 F1 3.463(8) no . 5_656
N2 C2 3.449(7) no . 1_556
N2 C6 3.365(7) no . 5_657
N2 C7 3.396(7) no . 5_657
C2 N1 3.534(6) no . 3_554
C2 N2 3.449(7) no . 1_554
C3 C7 3.472(6) no . 5_656
C4 C7 3.511(8) no . 3_554
C5 N1 3.552(6) no . 5_656
C5 C9 3.474(6) no . 5_656
C6 N1 3.572(6) no . 5_656
C6 N2 3.365(7) no . 5_657
C7 N2 3.396(7) no . 5_657
C7 C3 3.472(6) no . 5_656
C7 C4 3.511(8) no . 3_555
C9 F1 3.481(8) no . 5_656
C9 C5 3.474(6) no . 5_656
F1 H4 2.63(5) no . .
F1 H6 2.60(6) no . .
N1 H2 3.06(5) no . .
N1 H7 2.90(5) no . .
N1 H15 2.88(5) no . .
N2 H7 3.37(5) no . .
N2 H15 3.07(5) no . .
C1 H11 2.56(5) no . .
C1 H15 2.69(5) no . .
C2 H4 2.85(5) no . .
C2 H11 2.94(5) no . .
C3 H7 3.42(5) no . .
C4 H2 2.96(5) no . .
C4 H6 3.21(5) no . .
C5 H7 3.37(5) no . .
C6 H4 3.14(6) no . .
C8 H2 3.12(5) no . .
C8 H4 3.15(6) no . .
C8 H6 3.24(5) no . .
C9 H7 2.93(5) no . .
C9 H15 2.72(5) no . .
C10 H2 2.85(5) no . .
C10 H12 3.29(5) no . .
C10 H14 3.24(8) no . .
C11 H2 3.16(5) no . .
C11 H13 3.28(5) no . .
C11 H15 3.27(5) no . .
C12 H14 3.24(9) no . .
C13 H11 3.20(5) no . .
C13 H15 3.28(5) no . .
C14 H12 3.21(6) no . .
C15 H11 3.16(5) no . .
C15 H13 3.31(5) no . .
H2 H4 2.95(7) no . .
H2 H11 2.81(7) no . .
H6 H7 2.39(7) no . .
H11 H12 2.39(7) no . .
H12 H13 2.28(8) no . .
H13 H14 2.42(10) no . .
H14 H15 2.29(8) no . .
F1 H12 3.22(5) no . 8_555
F1 H13 3.44(6) no . 6_556
F1 H13 3.22(6) no . 8_555
N1 H2 2.96(5) no . 3_555
N2 H2 3.08(5) no . 1_556
N2 H6 2.74(5) no . 5_657
N2 H7 2.70(5) no . 5_657
N2 H11 2.77(5) no . 1_556
N2 H12 3.56(5) no . 4_555
N2 H13 2.84(5) no . 4_555
C1 H2 3.03(5) no . 3_555
C1 H6 3.37(5) no . 5_656
C1 H15 3.30(5) no . 3_554
C2 H2 3.36(5) no . 3_555
C2 H6 3.54(5) no . 5_656
C2 H15 3.27(5) no . 3_554
C3 H2 3.54(5) no . 3_555
C3 H4 3.28(6) no . 3_555
C3 H7 3.53(5) no . 5_656
C4 H4 3.27(6) no . 3_555
C5 H4 3.18(6) no . 3_555
C6 H4 3.08(5) no . 3_555
C7 H4 3.08(5) no . 3_555
C7 H7 3.57(5) no . 5_657
C8 H2 3.34(5) no . 3_555
C8 H4 3.15(5) no . 3_555
C9 H2 3.41(5) no . 1_556
C9 H2 3.54(5) no . 3_555
C9 H7 3.19(5) no . 5_657
C10 H12 3.50(5) no . 4_555
C10 H15 2.96(5) no . 3_554
C11 H6 3.47(5) no . 5_656
C11 H12 3.56(6) no . 4_555
C11 H14 3.58(7) no . 3_554
C11 H15 3.14(5) no . 3_554
C12 H12 3.38(6) no . 4_555
C12 H14 3.22(8) no . 3_554
C13 H11 3.29(5) no . 4_555
C13 H12 3.14(5) no . 4_555
C13 H14 3.15(8) no . 3_554
C14 H12 3.07(5) no . 4_555
C14 H14 3.43(8) no . 3_554
C15 H2 3.44(5) no . 3_555
C15 H12 3.25(5) no . 4_555
C15 H15 3.37(5) no . 3_554
H2 N1 2.96(5) no . 3_554
H2 N2 3.08(5) no . 1_554
H2 C1 3.03(5) no . 3_554
H2 C2 3.36(5) no . 3_554
H2 C3 3.54(5) no . 3_554
H2 C8 3.34(5) no . 3_554
H2 C9 3.41(5) no . 1_554
H2 C9 3.54(5) no . 3_554
H2 C15 3.44(5) no . 3_554
H2 H15 2.81(7) no . 3_554
H4 C3 3.28(6) no . 3_554
H4 C4 3.27(6) no . 3_554
H4 C5 3.18(6) no . 3_554
H4 C6 3.08(5) no . 3_554
H4 C7 3.08(5) no . 3_554
H4 C8 3.15(5) no . 3_554
H4 H7 3.10(8) no . 1_554
H6 N2 2.74(5) no . 5_657
H6 C1 3.37(5) no . 5_656
H6 C2 3.54(5) no . 5_656
H6 C11 3.47(5) no . 5_656
H6 H11 2.94(7) no . 5_656
H6 H13 2.86(8) no . 8_556
H7 N2 2.70(5) no . 5_657
H7 C3 3.53(5) no . 5_656
H7 C7 3.57(5) no . 5_657
H7 C9 3.19(5) no . 5_657
H7 H4 3.10(8) no . 1_556
H7 H7 2.60(7) no . 5_657
H11 N2 2.77(5) no . 1_554
H11 C13 3.29(5) no . 4_554
H11 H6 2.94(7) no . 5_656
H11 H13 3.05(8) no . 4_554
H11 H15 3.54(7) no . 1_554
H11 H15 3.35(7) no . 3_554
H12 F1 3.22(5) no . 8_455
H12 N2 3.56(5) no . 4_554
H12 C10 3.50(5) no . 4_554
H12 C11 3.56(6) no . 4_554
H12 C12 3.38(6) no . 4_554
H12 C13 3.14(5) no . 4_554
H12 C14 3.07(5) no . 4_554
H12 C15 3.25(5) no . 4_554
H12 H14 3.56(9) no . 3_554
H12 H14 3.49(9) no . 4_554
H13 F1 3.44(6) no . 6_456
H13 F1 3.22(6) no . 8_455
H13 N2 2.84(5) no . 4_554
H13 H6 2.86(8) no . 8_456
H13 H11 3.05(8) no . 4_555
H13 H14 3.40(10) no . 3_554
H14 C11 3.58(7) no . 3_555
H14 C12 3.22(8) no . 3_555
H14 C13 3.15(8) no . 3_555
H14 C14 3.43(8) no . 3_555
H14 H12 3.56(9) no . 3_555
H14 H12 3.49(9) no . 4_555
H14 H13 3.40(10) no . 3_555
H15 C1 3.30(5) no . 3_555
H15 C2 3.27(5) no . 3_555
H15 C10 2.96(5) no . 3_555
H15 C11 3.14(5) no . 3_555
H15 C15 3.37(5) no . 3_555
H15 H2 2.81(7) no . 3_555
H15 H11 3.54(7) no . 1_556
H15 H11 3.35(7) no . 3_555

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-fluoro-2-phenyl-1H-indole-1-carbonitrile
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method DMSO
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_User-defined
_database_code_depnum_ccdc_archive 'CCDC 1487090'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 N2'
_chemical_formula_moiety         'C16 H13 N2'
_chemical_formula_weight         233.29
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,+Z
3 +X,1/2-Y,1/2+Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 1/2+X,1/2-Y,-Z
7 -X,1/2+Y,1/2-Z
8 1/2+X,+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   25.555(2)
_cell_length_b                   14.1257(11)
_cell_length_c                   6.8724(6)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2480.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    16672
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.63
_cell_measurement_temperature    293
#------------------------------------------------------------------------------
_exptl_crystal_description       Chip
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984.00
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.766
_exptl_absorpt_correction_T_max  0.978

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku SCX mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 6.849
_diffrn_reflns_number            23443
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2840
_reflns_number_gt                1643
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1541
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_number_reflns         2840
_refine_ls_number_parameters     271
_refine_ls_goodness_of_fit_ref   0.920
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          2.128
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N N 0.0061 0.0033
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
C C 0.0033 0.0016
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
N1 N 0.57703(5) 0.10275(9) 0.3268(2) 0.0486(4) Uani 1.0 8 d . . .
N2 N 0.60721(6) 0.02170(15) 0.0299(3) 0.0812(6) Uani 1.0 8 d . . .
C1 C 0.60847(6) 0.13286(11) 0.4853(3) 0.0482(5) Uani 1.0 8 d . . .
C2 C 0.57606(7) 0.16243(12) 0.6299(3) 0.0511(5) Uani 1.0 8 d . . .
C3 C 0.52275(6) 0.15008(11) 0.5674(3) 0.0488(5) Uani 1.0 8 d . . .
C4 C 0.47390(7) 0.16724(13) 0.6527(3) 0.0543(5) Uani 1.0 8 d . . .
C5 C 0.42877(7) 0.14539(12) 0.5512(3) 0.0573(5) Uani 1.0 8 d . . .
C6 C 0.43227(8) 0.10526(13) 0.3650(4) 0.0581(6) Uani 1.0 8 d . . .
C7 C 0.47961(8) 0.08793(15) 0.2770(4) 0.0549(5) Uani 1.0 8 d . . .
C8 C 0.52387(6) 0.11196(11) 0.3795(3) 0.0467(5) Uani 1.0 8 d . . .
C9 C 0.37613(11) 0.1662(3) 0.6392(6) 0.0788(10) Uani 1.0 8 d . . .
C10 C 0.66575(6) 0.12844(11) 0.4723(3) 0.0510(5) Uani 1.0 8 d . . .
C11 C 0.69422(8) 0.09028(14) 0.6279(4) 0.0624(6) Uani 1.0 8 d . . .
C12 C 0.74805(9) 0.08549(16) 0.6174(4) 0.0761(7) Uani 1.0 8 d . . .
C13 C 0.77437(10) 0.11875(16) 0.4549(5) 0.0784(7) Uani 1.0 8 d . . .
C14 C 0.74675(9) 0.15769(15) 0.3035(5) 0.0747(7) Uani 1.0 8 d . . .
C15 C 0.69250(8) 0.16201(15) 0.3111(4) 0.0638(6) Uani 1.0 8 d . . .
C16 C 0.59357(7) 0.05901(14) 0.1688(3) 0.0540(5) Uani 1.0 8 d . . .
H2 H 0.5893(8) 0.1899(13) 0.760(3) 0.062(6) Uani 1.0 8 d . . .
H4 H 0.4723(7) 0.1924(14) 0.784(3) 0.066(6) Uani 1.0 8 d . . .
H6 H 0.3987(7) 0.0891(14) 0.292(3) 0.064(6) Uani 1.0 8 d . . .
H7 H 0.4808(8) 0.0606(15) 0.161(3) 0.067(6) Uani 1.0 8 d . . .
H9A H 0.3657(14) 0.230(3) 0.643(10) 0.22(3) Uani 1.0 8 d . . .
H9B H 0.3545(15) 0.123(4) 0.619(7) 0.18(3) Uani 1.0 8 d . . .
H9C H 0.3750(14) 0.162(5) 0.773(4) 0.15(3) Uani 1.0 8 d . . .
H11 H 0.6744(8) 0.0670(16) 0.751(3) 0.080(7) Uani 1.0 8 d . . .
H12 H 0.7694(8) 0.0580(17) 0.727(3) 0.090(8) Uani 1.0 8 d . . .
H13 H 0.8140(9) 0.1152(15) 0.442(4) 0.124(9) Uani 1.0 8 d . . .
H14 H 0.7656(9) 0.1802(17) 0.197(3) 0.093(8) Uani 1.0 8 d . . .
H15 H 0.6732(8) 0.1890(15) 0.205(3) 0.074(7) Uani 1.0 8 d . . .



#==============================================================================
_computing_data_collection       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
N1 C1 1.419(3) yes . .
N1 C8 1.412(2) yes . .
N1 C16 1.319(3) yes . .
N2 C16 1.145(3) yes . .
C1 C2 1.360(3) yes . .
C1 C10 1.468(3) yes . .
C2 C3 1.439(3) yes . .
C3 C4 1.401(3) yes . .
C3 C8 1.399(3) yes . .
C4 C5 1.383(3) yes . .
C5 C6 1.402(3) yes . .
C5 C9 1.504(4) yes . .
C6 C7 1.374(3) yes . .
C7 C8 1.375(3) yes . .
C10 C11 1.401(3) yes . .
C10 C15 1.385(3) yes . .
C11 C12 1.379(3) yes . .
C12 C13 1.386(4) yes . .
C13 C14 1.372(4) yes . .
C14 C15 1.389(3) yes . .
C2 H2 1.031(16) no . .
C4 H4 0.967(18) no . .
C6 H6 1.019(18) no . .
C7 H7 0.89(2) no . .
C9 H9A 0.94(5) no . .
C9 H9B 0.84(5) no . .
C9 H9C 0.92(3) no . .
C11 H11 1.040(18) no . .
C12 H12 1.01(2) no . .
C13 H13 1.02(3) no . .
C14 H14 0.93(2) no . .
C15 H15 0.961(18) no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C1 N1 C8 108.68(13) yes . . .
C1 N1 C16 126.23(14) yes . . .
C8 N1 C16 124.24(15) yes . . .
N1 C1 C2 107.96(14) yes . . .
N1 C1 C10 120.36(15) yes . . .
C2 C1 C10 131.68(17) yes . . .
C1 C2 C3 108.73(16) yes . . .
C2 C3 C4 134.24(18) yes . . .
C2 C3 C8 107.63(15) yes . . .
C4 C3 C8 118.13(16) yes . . .
C3 C4 C5 119.55(19) yes . . .
C4 C5 C6 119.84(18) yes . . .
C4 C5 C9 119.9(3) yes . . .
C6 C5 C9 120.2(3) yes . . .
C5 C6 C7 121.98(19) yes . . .
C6 C7 C8 117.1(2) yes . . .
N1 C8 C3 106.96(14) yes . . .
N1 C8 C7 129.61(17) yes . . .
C3 C8 C7 123.41(16) yes . . .
C1 C10 C11 119.20(17) yes . . .
C1 C10 C15 121.74(17) yes . . .
C11 C10 C15 119.06(17) yes . . .
C10 C11 C12 119.8(2) yes . . .
C11 C12 C13 120.7(3) yes . . .
C12 C13 C14 119.8(3) yes . . .
C13 C14 C15 120.2(3) yes . . .
C10 C15 C14 120.5(2) yes . . .
N1 C16 N2 178.8(2) yes . . .
C1 C2 H2 123.2(11) no . . .
C3 C2 H2 128.0(11) no . . .
C3 C4 H4 119.3(11) no . . .
C5 C4 H4 121.1(11) no . . .
C5 C6 H6 119.0(11) no . . .
C7 C6 H6 119.0(11) no . . .
C6 C7 H7 120.3(13) no . . .
C8 C7 H7 122.6(13) no . . .
C5 C9 H9A 117(3) no . . .
C5 C9 H9B 112(4) no . . .
C5 C9 H9C 115(3) no . . .
H9A C9 H9B 121(4) no . . .
H9A C9 H9C 92(6) no . . .
H9B C9 H9C 96(5) no . . .
C10 C11 H11 119.4(11) no . . .
C12 C11 H11 120.8(11) no . . .
C11 C12 H12 121.4(12) no . . .
C13 C12 H12 118.0(12) no . . .
C12 C13 H13 122.5(14) no . . .
C14 C13 H13 117.7(14) no . . .
C13 C14 H14 117.9(14) no . . .
C15 C14 H14 122.0(14) no . . .
C10 C15 H15 119.4(12) no . . .
C14 C15 H15 120.1(12) no . . .

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
_geom_torsion_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 C8 C3 1.64(16) no . . . .
C1 N1 C8 C7 -176.95(14) no . . . .
C8 N1 C1 C2 -1.67(16) no . . . .
C8 N1 C1 C10 178.39(12) no . . . .
C16 N1 C1 C2 -171.45(15) no . . . .
C16 N1 C1 C10 8.6(3) no . . . .
C16 N1 C8 C3 171.67(14) no . . . .
C16 N1 C8 C7 -6.9(3) no . . . .
N1 C1 C2 C3 1.03(18) no . . . .
N1 C1 C10 C11 -133.46(15) no . . . .
N1 C1 C10 C15 47.3(2) no . . . .
C2 C1 C10 C11 46.6(3) no . . . .
C2 C1 C10 C15 -132.63(19) no . . . .
C10 C1 C2 C3 -179.04(15) no . . . .
C1 C2 C3 C4 179.63(16) no . . . .
C1 C2 C3 C8 -0.02(18) no . . . .
C2 C3 C4 C5 -178.95(16) no . . . .
C2 C3 C8 N1 -1.00(17) no . . . .
C2 C3 C8 C7 177.70(14) no . . . .
C4 C3 C8 N1 179.28(14) no . . . .
C4 C3 C8 C7 -2.0(3) no . . . .
C8 C3 C4 C5 0.7(3) no . . . .
C3 C4 C5 C6 0.8(3) no . . . .
C3 C4 C5 C9 -178.19(14) no . . . .
C4 C5 C6 C7 -1.1(3) no . . . .
C9 C5 C6 C7 177.9(3) no . . . .
C5 C6 C7 C8 -0.2(3) no . . . .
C6 C7 C8 N1 -179.86(16) no . . . .
C6 C7 C8 C3 1.7(3) no . . . .
C1 C10 C11 C12 179.83(14) no . . . .
C1 C10 C15 C14 179.43(15) no . . . .
C11 C10 C15 C14 0.2(3) no . . . .
C15 C10 C11 C12 -0.9(3) no . . . .
C10 C11 C12 C13 0.5(3) no . . . .
C11 C12 C13 C14 0.6(4) no . . . .
C12 C13 C14 C15 -1.3(4) no . . . .
C13 C14 C15 C10 0.9(4) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
N1 C4 3.577(3) no . .
N1 C15 3.069(3) no . .
N2 C1 3.502(3) no . .
N2 C8 3.454(3) no . .
N2 C15 3.523(3) no . .
C2 C11 3.187(3) no . .
C2 C16 3.518(3) no . .
C3 C6 2.771(3) no . .
C3 C16 3.526(3) no . .
C4 C7 2.818(3) no . .
C5 C8 2.743(3) no . .
C7 C16 3.033(3) no . .
C10 C13 2.782(3) no . .
C10 C16 2.952(3) no . .
C11 C14 2.771(4) no . .
C12 C15 2.759(4) no . .
C15 C16 3.077(3) no . .
N1 C2 3.582(3) no . 3_554
N2 C2 3.485(3) no . 1_554
N2 C6 3.406(3) no . 5_655
N2 C7 3.431(3) no . 5_655
N2 C9 3.521(5) no . 5_656
C2 N1 3.582(3) no . 3_555
C2 N2 3.485(3) no . 1_556
C3 C7 3.529(3) no . 5_656
C4 C7 3.565(3) no . 3_555
C5 C16 3.517(3) no . 5_656
C6 N2 3.406(3) no . 5_655
C7 N2 3.431(3) no . 5_655
C7 C3 3.529(3) no . 5_656
C7 C4 3.565(3) no . 3_554
C9 N2 3.521(5) no . 5_656
C9 C16 3.530(5) no . 5_656
C16 C5 3.517(3) no . 5_656
C16 C9 3.530(5) no . 5_656
N1 H2 3.236(16) no . .
N1 H7 2.78(2) no . .
N1 H15 2.87(2) no . .
N2 H7 3.40(2) no . .
N2 H15 3.14(2) no . .
C1 H11 2.655(19) no . .
C1 H15 2.661(18) no . .
C2 H4 2.885(18) no . .
C2 H11 2.97(2) no . .
C3 H7 3.25(2) no . .
C4 H2 3.057(19) no . .
C4 H6 3.324(18) no . .
C4 H9A 2.90(4) no . .
C4 H9B 3.12(4) no . .
C4 H9C 2.66(4) no . .
C5 H7 3.23(2) no . .
C6 H4 3.292(18) no . .
C6 H9A 3.11(5) no . .
C6 H9B 2.66(5) no . .
C6 H9C 3.26(3) no . .
C8 H2 3.293(17) no . .
C8 H4 3.277(18) no . .
C8 H6 3.270(17) no . .
C9 H4 2.677(18) no . .
C9 H6 2.685(19) no . .
C10 H2 2.910(17) no . .
C10 H12 3.33(2) no . .
C10 H14 3.26(2) no . .
C11 H2 3.160(18) no . .
C11 H13 3.34(3) no . .
C11 H15 3.270(17) no . .
C12 H14 3.22(2) no . .
C13 H11 3.347(19) no . .
C13 H15 3.260(19) no . .
C14 H12 3.284(19) no . .
C15 H11 3.341(18) no . .
C15 H13 3.30(3) no . .
C16 H7 2.88(2) no . .
C16 H15 2.75(2) no . .
H2 H4 2.99(3) no . .
H2 H11 2.78(3) no . .
H4 H9A 2.94(5) no . .
H4 H9B 3.36(5) no . .
H4 H9C 2.53(4) no . .
H6 H7 2.32(3) no . .
H6 H9A 3.24(6) no . .
H6 H9B 2.56(5) no . .
H6 H9C 3.51(4) no . .
H11 H12 2.44(3) no . .
H12 H13 2.41(3) no . .
H13 H14 2.28(3) no . .
H14 H15 2.37(3) no . .
N1 H2 2.981(18) no . 3_554
N2 H2 3.049(17) no . 1_554
N2 H6 2.715(19) no . 5_655
N2 H7 2.85(2) no . 5_655
N2 H9B 3.31(5) no . 5_656
N2 H9C 2.96(6) no . 5_656
N2 H11 2.651(19) no . 1_554
N2 H13 2.86(3) no . 4_654
C1 H2 2.985(17) no . 3_554
C1 H6 3.494(19) no . 5_656
C1 H15 3.37(2) no . 3_555
C2 H2 3.307(17) no . 3_554
C2 H15 3.29(2) no . 3_555
C3 H2 3.531(17) no . 3_554
C3 H4 3.228(19) no . 3_554
C3 H7 3.52(2) no . 5_656
C4 H4 3.220(19) no . 3_554
C5 H4 3.142(19) no . 3_554
C6 H4 3.09(2) no . 3_554
C6 H9A 3.26(5) no . 3_554
C7 H4 3.11(2) no . 3_554
C8 H2 3.363(18) no . 3_554
C8 H4 3.13(2) no . 3_554
C9 H9C 3.50(5) no . 3_554
C9 H12 3.26(2) no . 8_456
C9 H13 3.52(3) no . 6_456
C9 H13 3.37(3) no . 8_456
C10 H2 3.540(18) no . 3_554
C10 H12 3.54(3) no . 4_654
C10 H15 3.04(2) no . 3_555
C11 H6 3.516(18) no . 5_656
C11 H12 3.58(2) no . 4_654
C11 H15 3.21(2) no . 3_555
C12 H9B 3.31(5) no . 8_556
C12 H9C 3.50(4) no . 8_556
C12 H12 3.39(2) no . 4_654
C12 H14 3.38(3) no . 3_555
C13 H9A 3.24(4) no . 6_556
C13 H9B 3.58(5) no . 8_556
C13 H9C 3.24(4) no . 8_556
C13 H11 3.25(2) no . 4_654
C13 H12 3.15(3) no . 4_654
C13 H14 3.30(3) no . 3_555
C14 H9A 3.45(4) no . 6_556
C14 H12 3.12(3) no . 4_654
C14 H14 3.57(2) no . 3_555
C15 H2 3.384(18) no . 3_554
C15 H12 3.31(3) no . 4_654
C15 H15 3.462(18) no . 3_555
C16 H2 3.366(16) no . 1_554
C16 H7 3.40(2) no . 5_655
C16 H9B 3.24(6) no . 5_656
C16 H9C 3.25(6) no . 5_656
C16 H11 3.538(18) no . 1_554
H2 N1 2.981(18) no . 3_555
H2 N2 3.049(17) no . 1_556
H2 C1 2.985(17) no . 3_555
H2 C2 3.307(17) no . 3_555
H2 C3 3.531(17) no . 3_555
H2 C8 3.363(18) no . 3_555
H2 C10 3.540(18) no . 3_555
H2 C15 3.384(18) no . 3_555
H2 C16 3.366(16) no . 1_556
H2 H15 2.77(3) no . 3_555
H4 C3 3.228(19) no . 3_555
H4 C4 3.220(19) no . 3_555
H4 C5 3.142(19) no . 3_555
H4 C6 3.09(2) no . 3_555
H4 C7 3.11(2) no . 3_555
H4 C8 3.13(2) no . 3_555
H4 H7 3.20(3) no . 1_556
H4 H7 3.60(3) no . 3_555
H6 N2 2.715(19) no . 5_655
H6 C1 3.494(19) no . 5_656
H6 C11 3.516(18) no . 5_656
H6 H9A 2.88(5) no . 3_554
H6 H9C 3.57(7) no . 3_554
H6 H11 2.91(3) no . 5_656
H6 H13 2.72(3) no . 8_455
H7 N2 2.85(2) no . 5_655
H7 C3 3.52(2) no . 5_656
H7 C16 3.40(2) no . 5_655
H7 H4 3.20(3) no . 1_554
H7 H4 3.60(3) no . 3_554
H7 H7 2.96(3) no . 5_655
H9A C6 3.26(5) no . 3_555
H9A C13 3.24(4) no . 6_456
H9A C14 3.45(4) no . 6_456
H9A H6 2.88(5) no . 3_555
H9A H9A 3.48(9) no . 3_554
H9A H9A 3.48(9) no . 3_555
H9A H9C 2.98(7) no . 3_554
H9A H12 3.57(5) no . 8_456
H9A H13 2.62(5) no . 6_456
H9A H13 3.54(6) no . 8_456
H9A H14 3.06(5) no . 6_456
H9A H14 3.53(6) no . 8_455
H9B N2 3.31(5) no . 5_656
H9B C12 3.31(5) no . 8_456
H9B C13 3.58(5) no . 8_456
H9B C16 3.24(6) no . 5_656
H9B H12 2.59(5) no . 8_456
H9B H13 3.19(6) no . 8_456
H9B H14 3.24(5) no . 8_455
H9C N2 2.96(6) no . 5_656
H9C C9 3.50(5) no . 3_555
H9C C12 3.50(4) no . 8_456
H9C C13 3.24(4) no . 8_456
H9C C16 3.25(6) no . 5_656
H9C H6 3.57(7) no . 3_555
H9C H9A 2.98(7) no . 3_555
H9C H12 3.07(5) no . 8_456
H9C H13 2.59(4) no . 8_456
H9C H14 3.58(6) no . 6_456
H11 N2 2.651(19) no . 1_556
H11 C13 3.25(2) no . 4_655
H11 C16 3.538(18) no . 1_556
H11 H6 2.91(3) no . 5_656
H11 H13 2.90(3) no . 4_655
H11 H15 3.56(3) no . 1_556
H11 H15 3.46(3) no . 3_555
H12 C9 3.26(2) no . 8_556
H12 C10 3.54(3) no . 4_655
H12 C11 3.58(2) no . 4_655
H12 C12 3.39(2) no . 4_655
H12 C13 3.15(3) no . 4_655
H12 C14 3.12(3) no . 4_655
H12 C15 3.31(3) no . 4_655
H12 H9A 3.57(5) no . 8_556
H12 H9B 2.59(5) no . 8_556
H12 H9C 3.07(5) no . 8_556
H12 H13 3.57(3) no . 4_655
H12 H14 3.49(4) no . 4_655
H13 N2 2.86(3) no . 4_655
H13 C9 3.52(3) no . 6_556
H13 C9 3.37(3) no . 8_556
H13 H6 2.72(3) no . 8_555
H13 H9A 2.62(5) no . 6_556
H13 H9A 3.54(6) no . 8_556
H13 H9B 3.19(6) no . 8_556
H13 H9C 2.59(4) no . 8_556
H13 H11 2.90(3) no . 4_654
H13 H12 3.57(3) no . 4_654
H13 H14 3.60(4) no . 3_555
H14 C12 3.38(3) no . 3_554
H14 C13 3.30(3) no . 3_554
H14 C14 3.57(2) no . 3_554
H14 H9A 3.06(5) no . 6_556
H14 H9A 3.53(6) no . 8_555
H14 H9B 3.24(5) no . 8_555
H14 H9C 3.58(6) no . 6_556
H14 H12 3.49(4) no . 4_654
H14 H13 3.60(4) no . 3_554
H15 C1 3.37(2) no . 3_554
H15 C2 3.29(2) no . 3_554
H15 C10 3.04(2) no . 3_554
H15 C11 3.21(2) no . 3_554
H15 C15 3.462(18) no . 3_554
H15 H2 2.77(3) no . 3_554
H15 H11 3.56(3) no . 1_554
H15 H11 3.46(3) no . 3_554

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        5-methyl-2-phenyl-1H-indole-1-carbonitrile
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Chloroform
