# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
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data_av_ht3h114
_audit_creation_method           SHELXL-2013

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

# CHEMICAL DATA

_chemical_name_systematic        
;
9-(4-Fluorophenyl)-9H-pyrido[2,3-b]indole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 F N2'
_chemical_formula_sum            'C17 H11 F N2'
_chemical_formula_weight         262.28

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'

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

# CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2637(4)
_cell_length_b                   9.6026(6)
_cell_length_c                   11.1057(8)
_cell_angle_alpha                78.235(4)
_cell_angle_beta                 81.016(4)
_cell_angle_gamma                74.565(4)
_cell_volume                     626.68(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1414
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      24.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.672399
_exptl_absorpt_correction_T_max  0.745810
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2973
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.233
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2973
_reflns_number_gt                1869
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 Refined as a 2-component twin.

 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.1307P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2973
_refine_ls_number_parameters     159
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0596
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9839(3) 0.7354(2) 0.09385(16) 0.0316(5) Uani 1 1 d . . . . .
C1A C 1.1463(14) 0.6576(17) 0.1613(8) 0.0299(3) Uani 0.398(14) 1 d DG . P A 1
N2A N 1.3602(16) 0.5882(17) 0.1172(7) 0.0294(7) Uani 0.398(14) 1 d DG . P A 1
C2A C 1.5148(12) 0.5129(12) 0.1996(9) 0.0311(7) Uani 0.398(14) 1 d DG . P A 1
H2A H 1.6610 0.4655 0.1694 0.037 Uiso 0.398(14) 1 calc R U P A 1
C3A C 1.4555(12) 0.5071(9) 0.3261(9) 0.0319(6) Uani 0.398(14) 1 d DG . P A 1
H3A H 1.5612 0.4557 0.3824 0.038 Uiso 0.398(14) 1 calc R U P A 1
C4A C 1.2417(14) 0.5765(11) 0.3703(7) 0.0322(6) Uani 0.398(14) 1 d DG . P A 1
H4A H 1.2012 0.5725 0.4567 0.039 Uiso 0.398(14) 1 calc R U P A 1
C5A C 1.0870(11) 0.6518(13) 0.2879(9) 0.0299(3) Uani 0.398(14) 1 d DG . P A 1
C6A C 0.8573(11) 0.7381(12) 0.2911(8) 0.0299(3) Uani 0.398(14) 1 d DG . P A 1
C7A C 0.7064(14) 0.7807(11) 0.3905(7) 0.0322(6) Uani 0.398(14) 1 d DG . P A 1
H7A H 0.7482 0.7511 0.4722 0.039 Uiso 0.398(14) 1 calc R U P A 1
C8A C 0.4942(12) 0.8667(9) 0.3703(7) 0.0319(6) Uani 0.398(14) 1 d DG . P A 1
H8A H 0.3910 0.8959 0.4382 0.038 Uiso 0.398(14) 1 calc R U P A 1
C9A C 0.4329(11) 0.9101(9) 0.2507(9) 0.0311(7) Uani 0.398(14) 1 d DG . P A 1
H9A H 0.2879 0.9689 0.2369 0.037 Uiso 0.398(14) 1 calc R U P A 1
C10A C 0.5839(16) 0.8675(13) 0.1513(7) 0.0327(8) Uani 0.398(14) 1 d DG . P A 1
H10A H 0.5421 0.8972 0.0696 0.039 Uiso 0.398(14) 1 calc R U P A 1
C11A C 0.7961(14) 0.7815(14) 0.1715(7) 0.0299(3) Uani 0.398(14) 1 d DG . P A 1
C1B C 0.7975(10) 0.7898(10) 0.1723(6) 0.0299(3) Uani 0.602(14) 1 d D . P A 2
N2B N 0.6020(10) 0.8720(8) 0.1286(5) 0.0327(8) Uani 0.602(14) 1 d D . P A 2
C2B C 0.4362(9) 0.9086(7) 0.2194(6) 0.0311(7) Uani 0.602(14) 1 d D . P A 2
H2B H 0.2943 0.9629 0.1956 0.037 Uiso 0.602(14) 1 calc R U P A 2
C3B C 0.4609(9) 0.8716(6) 0.3452(6) 0.0319(6) Uani 0.602(14) 1 d D . P A 2
H3B H 0.3382 0.9032 0.4035 0.038 Uiso 0.602(14) 1 calc R U P A 2
C4B C 0.6598(11) 0.7900(8) 0.3864(5) 0.0322(6) Uani 0.602(14) 1 d D . P A 2
H4B H 0.6769 0.7657 0.4723 0.039 Uiso 0.602(14) 1 calc R U P A 2
C5B C 0.8358(9) 0.7439(9) 0.2987(6) 0.0299(3) Uani 0.602(14) 1 d D . P A 2
C6B C 1.0628(9) 0.6589(9) 0.2937(7) 0.0299(3) Uani 0.602(14) 1 d D . P A 2
C7B C 1.2002(10) 0.5794(8) 0.3839(6) 0.0322(6) Uani 0.602(14) 1 d D . P A 2
H7B H 1.1483 0.5758 0.4692 0.039 Uiso 0.602(14) 1 calc R U P A 2
C8B C 1.4116(10) 0.5065(7) 0.3467(6) 0.0319(6) Uani 0.602(14) 1 d D . P A 2
H8B H 1.5081 0.4512 0.4068 0.038 Uiso 0.602(14) 1 calc R U P A 2
C9B C 1.4868(10) 0.5127(8) 0.2208(6) 0.0311(7) Uani 0.602(14) 1 d D . P A 2
H9B H 1.6361 0.4627 0.1988 0.037 Uiso 0.602(14) 1 calc R U P A 2
C10B C 1.3617(14) 0.5848(14) 0.1288(6) 0.0294(7) Uani 0.602(14) 1 d D . P A 2
H10B H 1.4148 0.5857 0.0438 0.035 Uiso 0.602(14) 1 calc R U P A 2
C11B C 1.1547(11) 0.6555(12) 0.1683(6) 0.0299(3) Uani 0.602(14) 1 d D . P A 2
C12 C 1.0009(4) 0.7580(3) -0.03863(19) 0.0301(5) Uani 1 1 d . . . . .
C13 C 0.8715(4) 0.6998(3) -0.0960(2) 0.0352(6) Uani 1 1 d . . . . .
H13 H 0.7717 0.6456 -0.0479 0.042 Uiso 1 1 calc R U . . .
C14 C 0.8888(4) 0.7211(3) -0.2237(2) 0.0357(6) Uani 1 1 d . . . . .
H14 H 0.8002 0.6830 -0.2646 0.043 Uiso 1 1 calc R U . . .
C15 C 1.0367(4) 0.7985(3) -0.2901(2) 0.0352(6) Uani 1 1 d . . . . .
F1 F 1.0524(3) 0.81921(18) -0.41541(12) 0.0517(5) Uani 1 1 d . . . . .
C16 C 1.1668(4) 0.8563(3) -0.2356(2) 0.0373(6) Uani 1 1 d . . . . .
H16 H 1.2674 0.9093 -0.2845 0.045 Uiso 1 1 calc R U . . .
C17 C 1.1486(4) 0.8357(3) -0.1074(2) 0.0346(6) Uani 1 1 d . . . . .
H17 H 1.2370 0.8748 -0.0672 0.042 Uiso 1 1 calc R U . . .


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1A 1.326(8) . ?
N1 C11A 1.373(6) . ?
N1 C1B 1.392(6) . ?
N1 C11B 1.413(6) . ?
N1 C12 1.434(3) . ?
C1A N2A 1.3900 . ?
C1A C5A 1.3900 . ?
N2A C2A 1.3900 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.456(4) . ?
C6A C7A 1.3900 . ?
C6A C11A 1.3900 . ?
C7A C8A 1.3900 . ?
C7A H7A 0.9500 . ?
C8A C9A 1.3900 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9500 . ?
C1B N2B 1.368(5) . ?
C1B C5B 1.421(5) . ?
N2B C2B 1.358(5) . ?
C2B C3B 1.392(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.374(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.393(5) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.438(4) . ?
C6B C7B 1.391(5) . ?
C6B C11B 1.425(5) . ?
C7B C8B 1.366(5) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.398(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.345(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.345(5) . ?
C10B H10B 0.9500 . ?
C12 C17 1.382(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 F1 1.357(3) . ?
C15 C16 1.367(3) . ?
C16 C17 1.388(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
_geom_angle_publ_flag
C1A N1 C11A 109.0(6) . . ?
C1B N1 C11B 107.6(4) . . ?
C1A N1 C12 124.7(5) . . ?
C11A N1 C12 126.2(4) . . ?
C1B N1 C12 126.2(3) . . ?
C11B N1 C12 126.1(3) . . ?
N1 C1A N2A 126.6(7) . . ?
N1 C1A C5A 113.4(7) . . ?
N2A C1A C5A 120.0 . . ?
C1A N2A C2A 120.0 . . ?
N2A C2A C3A 120.0 . . ?
N2A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A C1A 120.0 . . ?
C4A C5A C6A 138.7(7) . . ?
C1A C5A C6A 101.3(7) . . ?
C7A C6A C11A 120.0 . . ?
C7A C6A C5A 130.3(7) . . ?
C11A C6A C5A 109.6(7) . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
N1 C11A C10A 133.3(6) . . ?
N1 C11A C6A 106.4(6) . . ?
C10A C11A C6A 120.0 . . ?
N2B C1B N1 122.2(5) . . ?
N2B C1B C5B 126.1(4) . . ?
N1 C1B C5B 111.7(5) . . ?
C2B N2B C1B 113.5(3) . . ?
N2B C2B C3B 124.2(4) . . ?
N2B C2B H2B 117.9 . . ?
C3B C2B H2B 117.9 . . ?
C4B C3B C2B 121.1(4) . . ?
C4B C3B H3B 119.5 . . ?
C2B C3B H3B 119.5 . . ?
C3B C4B C5B 118.1(4) . . ?
C3B C4B H4B 121.0 . . ?
C5B C4B H4B 121.0 . . ?
C4B C5B C1B 117.0(4) . . ?
C4B C5B C6B 139.2(6) . . ?
C1B C5B C6B 103.8(5) . . ?
C7B C6B C11B 116.5(3) . . ?
C7B C6B C5B 133.4(6) . . ?
C11B C6B C5B 110.1(6) . . ?
C8B C7B C6B 118.4(4) . . ?
C8B C7B H7B 120.8 . . ?
C6B C7B H7B 120.8 . . ?
C7B C8B C9B 120.4(4) . . ?
C7B C8B H8B 119.8 . . ?
C9B C8B H8B 119.8 . . ?
C10B C9B C8B 124.4(4) . . ?
C10B C9B H9B 117.8 . . ?
C8B C9B H9B 117.8 . . ?
C9B C10B C11B 113.8(4) . . ?
C9B C10B H10B 123.1 . . ?
C11B C10B H10B 123.1 . . ?
C10B C11B N1 126.7(5) . . ?
C10B C11B C6B 126.4(4) . . ?
N1 C11B C6B 106.8(5) . . ?
C17 C12 C13 120.9(2) . . ?
C17 C12 N1 119.5(2) . . ?
C13 C12 N1 119.6(2) . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
F1 C15 C16 118.8(2) . . ?
F1 C15 C14 118.2(2) . . ?
C16 C15 C14 122.9(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C12 C17 C16 119.5(2) . . ?
C12 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11A N1 C1A N2A 177.9(8) . . . . ?
C1B N1 C1A N2A -178.5(8) . . . . ?
C11B N1 C1A N2A -143(35) . . . . ?
C12 N1 C1A N2A 1.7(13) . . . . ?
C11A N1 C1A C5A -3.5(12) . . . . ?
C1B N1 C1A C5A 0.1(11) . . . . ?
C11B N1 C1A C5A 36(33) . . . . ?
C12 N1 C1A C5A -179.7(5) . . . . ?
N1 C1A N2A C2A 178.5(14) . . . . ?
C5A C1A N2A C2A 0.0 . . . . ?
C1A N2A C2A C3A 0.0 . . . . ?
N2A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C1A 0.0 . . . . ?
C3A C4A C5A C6A -178.8(13) . . . . ?
N1 C1A C5A C4A -178.7(12) . . . . ?
N2A C1A C5A C4A 0.0 . . . . ?
N1 C1A C5A C6A 0.5(9) . . . . ?
N2A C1A C5A C6A 179.2(9) . . . . ?
C4A C5A C6A C7A 2.7(18) . . . . ?
C1A C5A C6A C7A -176.3(9) . . . . ?
C4A C5A C6A C11A -178.4(10) . . . . ?
C1A C5A C6A C11A 2.6(7) . . . . ?
C11A C6A C7A C8A 0.0 . . . . ?
C5A C6A C7A C8A 178.8(11) . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C1A N1 C11A C10A 178.2(9) . . . . ?
C1B N1 C11A C10A 86(11) . . . . ?
C11B N1 C11A C10A 177.0(10) . . . . ?
C12 N1 C11A C10A -5.7(13) . . . . ?
C1A N1 C11A C6A 4.9(10) . . . . ?
C1B N1 C11A C6A -88(11) . . . . ?
C11B N1 C11A C6A 3.8(8) . . . . ?
C12 N1 C11A C6A -178.9(4) . . . . ?
C9A C10A C11A N1 -172.5(13) . . . . ?
C9A C10A C11A C6A 0.0 . . . . ?
C7A C6A C11A N1 174.3(10) . . . . ?
C5A C6A C11A N1 -4.7(8) . . . . ?
C7A C6A C11A C10A 0.0 . . . . ?
C5A C6A C11A C10A -179.0(9) . . . . ?
C1A N1 C1B N2B -178.7(9) . . . . ?
C11A N1 C1B N2B -90(11) . . . . ?
C11B N1 C1B N2B -179.7(6) . . . . ?
C12 N1 C1B N2B 1.1(8) . . . . ?
C1A N1 C1B C5B -1.1(9) . . . . ?
C11A N1 C1B C5B 88(11) . . . . ?
C11B N1 C1B C5B -2.1(8) . . . . ?
C12 N1 C1B C5B 178.7(3) . . . . ?
N1 C1B N2B C2B 176.8(8) . . . . ?
C5B C1B N2B C2B -0.4(5) . . . . ?
C1B N2B C2B C3B 2.1(5) . . . . ?
N2B C2B C3B C4B -1.7(6) . . . . ?
C2B C3B C4B C5B -0.7(6) . . . . ?
C3B C4B C5B C1B 2.2(5) . . . . ?
C3B C4B C5B C6B -178.4(9) . . . . ?
N2B C1B C5B C4B -1.7(6) . . . . ?
N1 C1B C5B C4B -179.2(7) . . . . ?
N2B C1B C5B C6B 178.7(7) . . . . ?
N1 C1B C5B C6B 1.2(6) . . . . ?
C4B C5B C6B C7B 3.1(14) . . . . ?
C1B C5B C6B C7B -177.4(7) . . . . ?
C4B C5B C6B C11B -179.3(8) . . . . ?
C1B C5B C6B C11B 0.2(6) . . . . ?
C11B C6B C7B C8B 1.0(5) . . . . ?
C5B C6B C7B C8B 178.5(8) . . . . ?
C6B C7B C8B C9B 0.2(6) . . . . ?
C7B C8B C9B C10B -1.7(6) . . . . ?
C8B C9B C10B C11B 1.6(6) . . . . ?
C9B C10B C11B N1 -177.4(10) . . . . ?
C9B C10B C11B C6B -0.3(6) . . . . ?
C1A N1 C11B C10B 35(34) . . . . ?
C11A N1 C11B C10B 176.2(9) . . . . ?
C1B N1 C11B C10B 179.7(6) . . . . ?
C12 N1 C11B C10B -1.1(9) . . . . ?
C1A N1 C11B C6B -143(34) . . . . ?
C11A N1 C11B C6B -1.4(9) . . . . ?
C1B N1 C11B C6B 2.2(7) . . . . ?
C12 N1 C11B C6B -178.7(3) . . . . ?
C7B C6B C11B C10B -1.0(6) . . . . ?
C5B C6B C11B C10B -179.0(7) . . . . ?
C7B C6B C11B N1 176.6(8) . . . . ?
C5B C6B C11B N1 -1.5(7) . . . . ?
C1A N1 C12 C17 -64.7(9) . . . . ?
C11A N1 C12 C17 119.8(8) . . . . ?
C1B N1 C12 C17 115.5(6) . . . . ?
C11B N1 C12 C17 -63.5(7) . . . . ?
C1A N1 C12 C13 114.3(9) . . . . ?
C11A N1 C12 C13 -61.2(8) . . . . ?
C1B N1 C12 C13 -65.4(6) . . . . ?
C11B N1 C12 C13 115.6(6) . . . . ?
C17 C12 C13 C14 -0.7(4) . . . . ?
N1 C12 C13 C14 -179.7(2) . . . . ?
C12 C13 C14 C15 0.8(4) . . . . ?
C13 C14 C15 F1 -179.9(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
F1 C15 C16 C17 179.5(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C13 C12 C17 C16 0.3(4) . . . . ?
N1 C12 C17 C16 179.3(2) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-4

_database_code_depnum_ccdc_archive 'CCDC 1009792'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_is_jj2h210
_audit_creation_method           SHELXL-97

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

# CHEMICAL DATA

_chemical_name_systematic        
;
5-(4-Fluorophenyl)-5H-pyrido[3,2-b]indole
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 F N2'
_chemical_formula_sum            'C17 H11 F N2'
_chemical_formula_weight         262.28

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'

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

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.9224(7)
_cell_length_b                   11.0347(5)
_cell_length_c                   16.4227(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.077(2)
_cell_angle_gamma                90.00
_cell_volume                     2516.6(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4771
_cell_measurement_theta_min      4.715
_cell_measurement_theta_max      60.482

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9411
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

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

# EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15409
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3322
_reflns_number_gt                2167
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

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

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). The Uij of the 
 atoms F1a/F1b, C12a/C12b, C13a/C13b, C14a/C14b, C15a/C15b, C16a/C16b, C17a/C17b, 
 N2a/N2b, C1a/C6b, C2a/C11b, C3a/C10b, C4a/C9b, C5a/C8b, N1a/C7b, C6a/C1b, 
 C7a/N1b, C8a/C5b, C9a/C4b, C10a/C3b and C11a/C2b were constrained to be equal.
 The geometry in both parts of the disordered molecule were constrained to be 
 equal (esd 0.01).
 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.8289P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3322
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1155
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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

# ATOMIC COORDINATES AND DISPLACEMENT 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
N1A N 0.64306(15) 0.8014(2) 0.47293(11) 0.0460(6) Uani 0.738(4) 1 d P A 1
C1A C 0.5809(2) 0.8804(2) 0.43624(18) 0.0371(5) Uani 0.738(4) 1 d P A 1
C2A C 0.4894(2) 0.8459(2) 0.4000(2) 0.0355(5) Uani 0.738(4) 1 d P A 1
C3A C 0.4599(2) 0.7270(3) 0.4007(2) 0.0418(6) Uani 0.738(4) 1 d P A 1
H3A H 0.3990 0.7019 0.3769 0.050 Uiso 0.738(4) 1 calc PR A 1
C4A C 0.5247(2) 0.6462(2) 0.43851(15) 0.0471(6) Uani 0.738(4) 1 d P A 1
H4A H 0.5089 0.5626 0.4407 0.056 Uiso 0.738(4) 1 calc PR A 1
C5A C 0.61336(19) 0.6869(3) 0.47342(13) 0.0491(7) Uani 0.738(4) 1 d P A 1
H5A H 0.6554 0.6285 0.4993 0.059 Uiso 0.738(4) 1 calc PR A 1
C6A C 0.5903(3) 1.0086(2) 0.4221(2) 0.0350(7) Uani 0.738(4) 1 d P A 1
C7A C 0.6663(2) 1.0904(4) 0.43954(17) 0.0422(7) Uani 0.738(4) 1 d P A 1
H7A H 0.7246 1.0650 0.4681 0.051 Uiso 0.738(4) 1 calc PR A 1
C8A C 0.6538(2) 1.2074(3) 0.41418(17) 0.0472(7) Uani 0.738(4) 1 d P A 1
H8A H 0.7044 1.2643 0.4248 0.057 Uiso 0.738(4) 1 calc PR A 1
C9A C 0.5670(2) 1.2452(3) 0.3724(2) 0.0450(7) Uani 0.738(4) 1 d P A 1
H9A H 0.5602 1.3277 0.3565 0.054 Uiso 0.738(4) 1 calc PR A 1
C10A C 0.4922(3) 1.1670(4) 0.3541(3) 0.0387(7) Uani 0.738(4) 1 d P A 1
H10A H 0.4336 1.1920 0.3259 0.046 Uiso 0.738(4) 1 calc PR A 1
C11A C 0.5090(6) 1.0454(7) 0.3804(5) 0.0364(10) Uani 0.738(4) 1 d P A 1
N2A N 0.4418(5) 0.9496(4) 0.3650(4) 0.0342(7) Uani 0.738(4) 1 d P A 1
C12A C 0.3393(3) 0.8733(5) 0.2547(3) 0.0364(8) Uani 0.738(4) 1 d PG A 1
H12A H 0.3897 0.8216 0.2399 0.044 Uiso 0.738(4) 1 calc PR A 1
C13A C 0.2512(3) 0.8730(6) 0.2092(3) 0.0418(10) Uani 0.738(4) 1 d PG A 1
H13A H 0.2415 0.8210 0.1632 0.050 Uiso 0.738(4) 1 calc PR A 1
C14A C 0.1775(3) 0.9487(6) 0.2309(3) 0.0411(8) Uani 0.738(4) 1 d PG A 1
C15A C 0.1918(4) 1.0248(6) 0.2981(4) 0.0438(8) Uani 0.738(4) 1 d PG A 1
H15A H 0.1413 1.0765 0.3130 0.053 Uiso 0.738(4) 1 calc PR A 1
C16A C 0.2798(4) 1.0251(6) 0.3437(4) 0.0424(6) Uani 0.738(4) 1 d PG A 1
H16A H 0.2896 1.0770 0.3896 0.051 Uiso 0.738(4) 1 calc PR A 1
C17A C 0.3536(3) 0.9493(5) 0.3220(3) 0.0332(6) Uani 0.738(4) 1 d PG A 1
F1A F 0.0937(7) 0.9482(8) 0.1881(6) 0.0614(10) Uani 0.738(4) 1 d P A 1
N1B N 0.6656(7) 1.0370(6) 0.4482(5) 0.0422(7) Uani 0.262(4) 1 d P A 2
C1B C 0.5900(11) 0.9697(10) 0.4269(8) 0.0350(7) Uani 0.262(4) 1 d P A 2
C2B C 0.496(2) 1.024(2) 0.3773(16) 0.0364(10) Uani 0.262(4) 1 d P A 2
C3B C 0.5081(11) 1.1376(13) 0.3583(10) 0.0387(7) Uani 0.262(4) 1 d P A 2
H3B H 0.4572 1.1752 0.3260 0.046 Uiso 0.262(4) 1 calc PR A 2
C4B C 0.5899(8) 1.2105(10) 0.3814(7) 0.0450(7) Uani 0.262(4) 1 d P A 2
H4B H 0.5937 1.2937 0.3671 0.054 Uiso 0.262(4) 1 calc PR A 2
C5B C 0.6622(8) 1.1520(12) 0.4255(7) 0.0472(7) Uani 0.262(4) 1 d P A 2
H5B H 0.7170 1.1996 0.4420 0.057 Uiso 0.262(4) 1 calc PR A 2
C6B C 0.5674(6) 0.8450(6) 0.4355(6) 0.0371(5) Uani 0.262(4) 1 d PG A 2
C7B C 0.6190(4) 0.7524(7) 0.4759(4) 0.0460(6) Uani 0.262(4) 1 d PG A 2
H7B H 0.6804 0.7687 0.5027 0.055 Uiso 0.262(4) 1 calc PR A 2
C8B C 0.5809(5) 0.6361(6) 0.4771(4) 0.0491(7) Uani 0.262(4) 1 d PG A 2
H8B H 0.6161 0.5728 0.5047 0.059 Uiso 0.262(4) 1 calc PR A 2
C9B C 0.4911(5) 0.6123(6) 0.4379(5) 0.0471(6) Uani 0.262(4) 1 d PG A 2
H9B H 0.4650 0.5327 0.4387 0.056 Uiso 0.262(4) 1 calc PR A 2
C10B C 0.4395(5) 0.7048(8) 0.3974(6) 0.0418(6) Uani 0.262(4) 1 d PG A 2
H10B H 0.3781 0.6885 0.3706 0.050 Uiso 0.262(4) 1 calc PR A 2
C11B C 0.4776(6) 0.8211(7) 0.3962(7) 0.0355(5) Uani 0.262(4) 1 d PG A 2
N2B N 0.4467(16) 0.9224(14) 0.3678(12) 0.0342(7) Uani 0.262(4) 1 d P A 2
C12B C 0.3468(11) 0.9378(18) 0.3152(11) 0.0364(8) Uani 0.262(4) 1 d P A 2
C13B C 0.3231(11) 0.8679(17) 0.2471(12) 0.0418(10) Uani 0.262(4) 1 d P A 2
H13B H 0.3695 0.8140 0.2277 0.050 Uiso 0.262(4) 1 calc PR A 2
C14B C 0.2357(14) 0.8746(19) 0.2081(10) 0.0411(8) Uani 0.262(4) 1 d P A 2
H14B H 0.2147 0.8249 0.1631 0.049 Uiso 0.262(4) 1 calc PR A 2
C15B C 0.1820(10) 0.959(2) 0.2397(12) 0.0438(8) Uani 0.262(4) 1 d P A 2
C16B C 0.1957(12) 1.034(2) 0.2999(12) 0.0424(6) Uani 0.262(4) 1 d P A 2
H16B H 0.1497 1.0927 0.3130 0.051 Uiso 0.262(4) 1 calc PR A 2
C17B C 0.2832(12) 1.0196(15) 0.3434(9) 0.0332(6) Uani 0.262(4) 1 d P A 2
H17B H 0.2990 1.0653 0.3915 0.040 Uiso 0.262(4) 1 calc PR A 2
F1B F 0.085(2) 0.968(2) 0.194(2) 0.0614(10) Uani 0.262(4) 1 d P A 2


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

# MOLECULAR GEOMETRY

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C5A 1.330(3) . ?
N1A C1A 1.341(3) . ?
C1A C2A 1.419(2) . ?
C1A C6A 1.440(3) . ?
C2A C3A 1.376(3) . ?
C2A N2A 1.423(4) . ?
C3A C4A 1.384(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.397(3) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A C11A 1.345(10) . ?
C6A C7A 1.405(5) . ?
C7A C8A 1.365(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.409(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.370(6) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.424(9) . ?
C10A H10A 0.9500 . ?
C11A N2A 1.422(8) . ?
N2A C17A 1.373(7) . ?
C12A C13A 1.3900 . ?
C12A C17A 1.3900 . ?
C12A H12A 0.9500 . ?
C13A C14A 1.3900 . ?
C13A H13A 0.9500 . ?
C14A F1A 1.318(10) . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?
C15A H15A 0.9500 . ?
C16A C17A 1.3900 . ?
C16A H16A 0.9500 . ?
N1B C1B 1.316(17) . ?
N1B C5B 1.322(11) . ?
C1B C6B 1.421(11) . ?
C1B C2B 1.60(3) . ?
C2B C3B 1.31(3) . ?
C2B N2B 1.32(3) . ?
C3B C4B 1.42(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.361(12) . ?
C4B H4B 0.9500 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C6B C11B 1.3900 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B C9B 1.3900 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B N2B 1.274(14) . ?
N2B C12B 1.59(2) . ?
C12B C17B 1.368(9) . ?
C12B C13B 1.378(10) . ?
C13B C14B 1.336(10) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.320(10) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.293(10) . ?
C15B F1B 1.50(3) . ?
C16B C17B 1.376(7) . ?
C16B H16B 0.9500 . ?
C17B H17B 0.9500 . ?

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
_geom_angle_publ_flag
C5A N1A C1A 115.45(17) . . ?
N1A C1A C2A 123.0(2) . . ?
N1A C1A C6A 130.4(3) . . ?
C2A C1A C6A 106.6(3) . . ?
C3A C2A C1A 120.79(17) . . ?
C3A C2A N2A 129.8(3) . . ?
C1A C2A N2A 109.4(3) . . ?
C2A C3A C4A 115.66(19) . . ?
C2A C3A H3A 122.2 . . ?
C4A C3A H3A 122.2 . . ?
C3A C4A C5A 120.4(2) . . ?
C3A C4A H4A 119.8 . . ?
C5A C4A H4A 119.8 . . ?
N1A C5A C4A 124.66(19) . . ?
N1A C5A H5A 117.7 . . ?
C4A C5A H5A 117.7 . . ?
C11A C6A C7A 120.3(3) . . ?
C11A C6A C1A 107.2(4) . . ?
C7A C6A C1A 132.4(3) . . ?
C8A C7A C6A 118.0(3) . . ?
C8A C7A H7A 121.0 . . ?
C6A C7A H7A 121.0 . . ?
C7A C8A C9A 120.9(3) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A H8A 119.5 . . ?
C10A C9A C8A 122.3(2) . . ?
C10A C9A H9A 118.9 . . ?
C8A C9A H9A 118.9 . . ?
C9A C10A C11A 114.9(4) . . ?
C9A C10A H10A 122.5 . . ?
C11A C10A H10A 122.5 . . ?
C6A C11A N2A 112.7(6) . . ?
C6A C11A C10A 123.6(4) . . ?
N2A C11A C10A 123.7(7) . . ?
C17A N2A C11A 130.2(5) . . ?
C17A N2A C2A 125.5(5) . . ?
C11A N2A C2A 104.1(5) . . ?
C13A C12A C17A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C17A C12A H12A 120.0 . . ?
C12A C13A C14A 120.0 . . ?
C12A C13A H13A 120.0 . . ?
C14A C13A H13A 120.0 . . ?
F1A C14A C15A 119.9(5) . . ?
F1A C14A C13A 120.1(5) . . ?
C15A C14A C13A 120.0 . . ?
C14A C15A C16A 120.0 . . ?
C14A C15A H15A 120.0 . . ?
C16A C15A H15A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
N2A C17A C16A 121.1(4) . . ?
N2A C17A C12A 118.9(4) . . ?
C16A C17A C12A 120.0 . . ?
C1B N1B C5B 117.0(10) . . ?
N1B C1B C6B 134.4(11) . . ?
N1B C1B C2B 122.1(11) . . ?
C6B C1B C2B 103.5(12) . . ?
C3B C2B N2B 149(2) . . ?
C3B C2B C1B 111.7(16) . . ?
N2B C2B C1B 98(2) . . ?
C2B C3B C4B 126.1(14) . . ?
C2B C3B H3B 116.9 . . ?
C4B C3B H3B 116.9 . . ?
C5B C4B C3B 114.9(10) . . ?
C5B C4B H4B 122.6 . . ?
C3B C4B H4B 122.6 . . ?
N1B C5B C4B 128.1(12) . . ?
N1B C5B H5B 116.0 . . ?
C4B C5B H5B 116.0 . . ?
C7B C6B C11B 120.0 . . ?
C7B C6B C1B 130.4(8) . . ?
C11B C6B C1B 109.6(8) . . ?
C6B C7B C8B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C9B C8B C7B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
N2B C11B C10B 134.1(11) . . ?
N2B C11B C6B 105.9(11) . . ?
C10B C11B C6B 120.0 . . ?
C11B N2B C2B 123(2) . . ?
C11B N2B C12B 123.5(17) . . ?
C2B N2B C12B 113.9(18) . . ?
C17B C12B C13B 121.3(6) . . ?
C17B C12B N2B 116.6(13) . . ?
C13B C12B N2B 122.0(13) . . ?
C14B C13B C12B 121.0(7) . . ?
C14B C13B H13B 119.5 . . ?
C12B C13B H13B 119.5 . . ?
C15B C14B C13B 111.9(6) . . ?
C15B C14B H14B 124.1 . . ?
C13B C14B H14B 124.1 . . ?
C16B C15B C14B 133.8(7) . . ?
C16B C15B F1B 114.7(15) . . ?
C14B C15B F1B 111.5(15) . . ?
C15B C16B C17B 113.8(6) . . ?
C15B C16B H16B 123.1 . . ?
C17B C16B H16B 123.1 . . ?
C12B C17B C16B 118.0(6) . . ?
C12B C17B H17B 121.0 . . ?
C16B C17B H17B 121.0 . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5A N1A C1A C2A -0.1(3) . . . . ?
C5A N1A C1A C6A -177.6(4) . . . . ?
N1A C1A C2A C3A -0.1(3) . . . . ?
C6A C1A C2A C3A 177.8(3) . . . . ?
N1A C1A C2A N2A -178.9(4) . . . . ?
C6A C1A C2A N2A -0.9(4) . . . . ?
C1A C2A C3A C4A -0.1(3) . . . . ?
N2A C2A C3A C4A 178.4(5) . . . . ?
C2A C3A C4A C5A 0.5(3) . . . . ?
C1A N1A C5A C4A 0.6(3) . . . . ?
C3A C4A C5A N1A -0.8(3) . . . . ?
N1A C1A C6A C11A 177.9(5) . . . . ?
C2A C1A C6A C11A 0.2(5) . . . . ?
N1A C1A C6A C7A 1.9(7) . . . . ?
C2A C1A C6A C7A -175.9(4) . . . . ?
C11A C6A C7A C8A 1.2(7) . . . . ?
C1A C6A C7A C8A 176.8(4) . . . . ?
C6A C7A C8A C9A 0.6(5) . . . . ?
C7A C8A C9A C10A -1.1(5) . . . . ?
C8A C9A C10A C11A 0.0(7) . . . . ?
C7A C6A C11A N2A 177.3(5) . . . . ?
C1A C6A C11A N2A 0.6(8) . . . . ?
C7A C6A C11A C10A -2.4(11) . . . . ?
C1A C6A C11A C10A -179.1(7) . . . . ?
C9A C10A C11A C6A 1.8(10) . . . . ?
C9A C10A C11A N2A -177.9(7) . . . . ?
C6A C11A N2A C17A -176.9(7) . . . . ?
C10A C11A N2A C17A 2.8(14) . . . . ?
C6A C11A N2A C2A -1.1(9) . . . . ?
C10A C11A N2A C2A 178.6(7) . . . . ?
C3A C2A N2A C17A -1.3(9) . . . . ?
C1A C2A N2A C17A 177.2(6) . . . . ?
C3A C2A N2A C11A -177.4(5) . . . . ?
C1A C2A N2A C11A 1.2(6) . . . . ?
C17A C12A C13A C14A 0.0 . . . . ?
C12A C13A C14A F1A -179.6(8) . . . . ?
C12A C13A C14A C15A 0.0 . . . . ?
F1A C14A C15A C16A 179.6(8) . . . . ?
C13A C14A C15A C16A 0.0 . . . . ?
C14A C15A C16A C17A 0.0 . . . . ?
C11A N2A C17A C16A -58.9(10) . . . . ?
C2A N2A C17A C16A 126.2(6) . . . . ?
C11A N2A C17A C12A 119.9(8) . . . . ?
C2A N2A C17A C12A -55.1(8) . . . . ?
C15A C16A C17A N2A 178.7(6) . . . . ?
C15A C16A C17A C12A 0.0 . . . . ?
C13A C12A C17A N2A -178.8(5) . . . . ?
C13A C12A C17A C16A 0.0 . . . . ?
C5B N1B C1B C6B 176.5(15) . . . . ?
C5B N1B C1B C2B -1(2) . . . . ?
N1B C1B C2B C3B 3(3) . . . . ?
C6B C1B C2B C3B -175.0(19) . . . . ?
N1B C1B C2B N2B 176.7(16) . . . . ?
C6B C1B C2B N2B -2(2) . . . . ?
N2B C2B C3B C4B -171(4) . . . . ?
C1B C2B C3B C4B -4(3) . . . . ?
C2B C3B C4B C5B 2(3) . . . . ?
C1B N1B C5B C4B -1(2) . . . . ?
C3B C4B C5B N1B 1(2) . . . . ?
N1B C1B C6B C7B 5(2) . . . . ?
C2B C1B C6B C7B -177.1(12) . . . . ?
N1B C1B C6B C11B -176.1(14) . . . . ?
C2B C1B C6B C11B 1.9(14) . . . . ?
C11B C6B C7B C8B 0.0 . . . . ?
C1B C6B C7B C8B 178.9(13) . . . . ?
C6B C7B C8B C9B 0.0 . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B N2B -176.9(18) . . . . ?
C9B C10B C11B C6B 0.0 . . . . ?
C7B C6B C11B N2B 177.7(14) . . . . ?
C1B C6B C11B N2B -1.4(13) . . . . ?
C7B C6B C11B C10B 0.0 . . . . ?
C1B C6B C11B C10B -179.1(10) . . . . ?
C10B C11B N2B C2B 177.3(18) . . . . ?
C6B C11B N2B C2B 0(3) . . . . ?
C10B C11B N2B C12B -5(3) . . . . ?
C6B C11B N2B C12B 178.0(16) . . . . ?
C3B C2B N2B C11B 169(4) . . . . ?
C1B C2B N2B C11B 1(3) . . . . ?
C3B C2B N2B C12B -9(6) . . . . ?
C1B C2B N2B C12B -177.0(16) . . . . ?
C11B N2B C12B C17B 124.0(19) . . . . ?
C2B N2B C12B C17B -58(2) . . . . ?
C11B N2B C12B C13B -53(3) . . . . ?
C2B N2B C12B C13B 125(2) . . . . ?
C17B C12B C13B C14B -2.4(10) . . . . ?
N2B C12B C13B C14B 174.0(18) . . . . ?
C12B C13B C14B C15B 3.9(10) . . . . ?
C13B C14B C15B C16B -0.9(11) . . . . ?
C13B C14B C15B F1B 178(2) . . . . ?
C14B C15B C16B C17B -3.7(12) . . . . ?
F1B C15B C16B C17B 177(2) . . . . ?
C13B C12B C17B C16B -2.4(10) . . . . ?
N2B C12B C17B C16B -179.0(15) . . . . ?
C15B C16B C17B C12B 5.0(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.033

#=====================  End of is_jj2h210 =================================

#=====================  End of CIF submission =================================
_database_code_depnum_ccdc_archive 'CCDC 1009793'
