# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_FO4976
_database_code_depnum_ccdc_archive 'CCDC 1426897'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H19 N'
_chemical_formula_sum            'C23 H19 N'
_chemical_formula_weight         309.39

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.2645(2)
_cell_length_b                   22.7706(5)
_cell_length_c                   10.5374(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.257(1)
_cell_angle_gamma                90
_cell_volume                     1729.10(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.075
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11309
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.46
_reflns_number_total             3947
_reflns_number_gt                3367
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0315P)²+0.7151P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3947
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.94398(14) 0.04385(4) 0.78064(10) 0.0217(2) Uani 1 1 d . . .
C1 C 0.89640(16) -0.00973(5) 0.72008(11) 0.0201(2) Uani 1 1 d . . .
C2 C 1.00770(17) -0.03649(5) 0.64400(12) 0.0222(3) Uani 1 1 d . . .
H2 H 1.119(2) -0.0162(6) 0.6218(14) 0.026(4) Uiso 1 1 d . . .
C3 C 0.97995(16) -0.09408(5) 0.59261(11) 0.0225(3) Uani 1 1 d . . .
C4 C 0.96363(17) -0.14189(6) 0.54401(12) 0.0229(3) Uani 1 1 d . . .
C5 C 0.93128(17) -0.19823(5) 0.48456(11) 0.0220(3) Uani 1 1 d . . .
C6 C 0.78606(19) -0.23382(6) 0.51554(13) 0.0268(3) Uani 1 1 d . . .
H6 H 0.709(2) -0.2203(7) 0.5813(15) 0.032(4) Uiso 1 1 d . . .
C7 C 0.7515(2) -0.28753(6) 0.45528(14) 0.0309(3) Uani 1 1 d . . .
H7 H 0.648(2) -0.3115(7) 0.4785(15) 0.036(4) Uiso 1 1 d . . .
C8 C 0.8592(2) -0.30636(6) 0.36389(13) 0.0306(3) Uani 1 1 d . . .
H8 H 0.835(2) -0.3437(8) 0.3201(16) 0.043(5) Uiso 1 1 d . . .
C9 C 1.0039(2) -0.27185(6) 0.33330(13) 0.0297(3) Uani 1 1 d . . .
H9 H 1.083(2) -0.2850(7) 0.2706(16) 0.039(4) Uiso 1 1 d . . .
C10 C 1.04058(18) -0.21798(6) 0.39305(12) 0.0253(3) Uani 1 1 d . . .
H10 H 1.141(2) -0.1938(7) 0.3725(14) 0.030(4) Uiso 1 1 d . . .
C11 C 0.72477(16) -0.03787(5) 0.75462(12) 0.0202(2) Uani 1 1 d . . .
C12 C 0.60183(17) -0.06618(6) 0.66181(12) 0.0235(3) Uani 1 1 d . . .
H12 H 0.625(2) -0.0655(6) 0.5723(14) 0.027(4) Uiso 1 1 d . . .
C13 C 0.44723(18) -0.09542(6) 0.69539(13) 0.0275(3) Uani 1 1 d . . .
H13 H 0.365(2) -0.1165(7) 0.6300(15) 0.033(4) Uiso 1 1 d . . .
C14 C 0.41198(18) -0.09584(6) 0.82209(14) 0.0287(3) Uani 1 1 d . . .
H14 H 0.301(2) -0.1172(7) 0.8464(14) 0.034(4) Uiso 1 1 d . . .
C15 C 0.53213(19) -0.06722(6) 0.91481(13) 0.0267(3) Uani 1 1 d . . .
H15 H 0.510(2) -0.0676(7) 1.0044(16) 0.035(4) Uiso 1 1 d . . .
C16 C 0.68759(18) -0.03821(5) 0.88153(12) 0.0235(3) Uani 1 1 d . . .
H16 H 0.773(2) -0.0180(7) 0.9477(14) 0.028(4) Uiso 1 1 d . . .
C17 C 1.13260(18) 0.06622(6) 0.77638(14) 0.0260(3) Uani 1 1 d . . .
H17C H 1.225(2) 0.0341(7) 0.8060(14) 0.027(4) Uiso 1 1 d . . .
H17B H 1.151(2) 0.0793(7) 0.6892(15) 0.033(4) Uiso 1 1 d . . .
H17A H 1.153(2) 0.0999(7) 0.8371(15) 0.032(4) Uiso 1 1 d . . .
C18 C 0.80309(17) 0.08794(5) 0.77836(11) 0.0216(2) Uani 1 1 d . . .
C19 C 0.65819(17) 0.09086(5) 0.67821(12) 0.0233(3) Uani 1 1 d . . .
H19 H 0.652(2) 0.0615(7) 0.6077(15) 0.029(4) Uiso 1 1 d . . .
C20 C 0.52523(18) 0.13484(6) 0.67613(13) 0.0271(3) Uani 1 1 d . . .
H20 H 0.421(2) 0.1365(7) 0.6043(16) 0.038(4) Uiso 1 1 d . . .
C21 C 0.5370(2) 0.17694(6) 0.77199(14) 0.0313(3) Uani 1 1 d . . .
H21 H 0.443(2) 0.2096(8) 0.7700(16) 0.041(5) Uiso 1 1 d . . .
C22 C 0.6819(2) 0.17435(6) 0.87119(14) 0.0311(3) Uani 1 1 d . . .
H22 H 0.693(2) 0.2051(7) 0.9390(16) 0.039(4) Uiso 1 1 d . . .
C23 C 0.81346(19) 0.13004(6) 0.87536(13) 0.0269(3) Uani 1 1 d . . .
H23 H 0.914(2) 0.1281(7) 0.9447(15) 0.032(4) Uiso 1 1 d . . .


_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 C1 1.3999(15) . ?
N1 C18 1.4317(16) . ?
N1 C17 1.4678(16) . ?
C1 C2 1.3533(17) . ?
C1 C11 1.4874(17) . ?
C2 C3 1.4234(17) . ?
C2 H2 0.984(15) . ?
C3 C4 1.2027(18) . ?
C4 C5 1.4339(17) . ?
C5 C10 1.3986(18) . ?
C5 C6 1.4012(18) . ?
C6 C7 1.3863(19) . ?
C6 H6 0.994(16) . ?
C7 C8 1.383(2) . ?
C7 H7 0.984(16) . ?
C8 C9 1.383(2) . ?
C8 H8 0.972(18) . ?
C9 C10 1.3891(18) . ?
C9 H9 0.976(17) . ?
C10 H10 0.959(16) . ?
C11 C12 1.3960(17) . ?
C11 C16 1.3974(18) . ?
C12 C13 1.3893(18) . ?
C12 H12 0.979(15) . ?
C13 C14 1.391(2) . ?
C13 H13 0.979(16) . ?
C14 C15 1.3876(19) . ?
C14 H14 1.001(16) . ?
C15 C16 1.3910(18) . ?
C15 H15 0.978(17) . ?
C16 H16 0.988(15) . ?
C17 H17C 1.015(15) . ?
C17 H17B 0.990(16) . ?
C17 H17A 0.998(16) . ?
C18 C19 1.3948(17) . ?
C18 C23 1.3964(17) . ?
C19 C20 1.3897(18) . ?
C19 H19 0.997(15) . ?
C20 C21 1.3873(19) . ?
C20 H20 1.001(16) . ?
C21 C22 1.388(2) . ?
C21 H21 1.011(17) . ?
C22 C23 1.386(2) . ?
C22 H22 0.996(17) . ?
C23 H23 0.966(16) . ?

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
C1 N1 C18 117.95(10) . . ?
C1 N1 C17 117.79(10) . . ?
C18 N1 C17 115.11(10) . . ?
C2 C1 N1 122.06(11) . . ?
C2 C1 C11 122.21(11) . . ?
N1 C1 C11 115.49(10) . . ?
C1 C2 C3 125.01(12) . . ?
C1 C2 H2 119.9(9) . . ?
C3 C2 H2 115.1(9) . . ?
C4 C3 C2 176.09(13) . . ?
C3 C4 C5 176.23(13) . . ?
C10 C5 C6 118.97(12) . . ?
C10 C5 C4 120.86(12) . . ?
C6 C5 C4 120.15(12) . . ?
C7 C6 C5 120.11(13) . . ?
C7 C6 H6 120.5(9) . . ?
C5 C6 H6 119.4(9) . . ?
C8 C7 C6 120.45(13) . . ?
C8 C7 H7 121.2(10) . . ?
C6 C7 H7 118.4(10) . . ?
C9 C8 C7 119.97(13) . . ?
C9 C8 H8 119.0(10) . . ?
C7 C8 H8 121.0(10) . . ?
C8 C9 C10 120.29(13) . . ?
C8 C9 H9 120.9(10) . . ?
C10 C9 H9 118.8(10) . . ?
C9 C10 C5 120.21(12) . . ?
C9 C10 H10 120.8(9) . . ?
C5 C10 H10 119.0(9) . . ?
C12 C11 C16 118.95(11) . . ?
C12 C11 C1 120.62(11) . . ?
C16 C11 C1 120.39(11) . . ?
C13 C12 C11 120.60(12) . . ?
C13 C12 H12 119.7(9) . . ?
C11 C12 H12 119.7(9) . . ?
C12 C13 C14 120.04(12) . . ?
C12 C13 H13 119.8(9) . . ?
C14 C13 H13 120.1(9) . . ?
C15 C14 C13 119.80(13) . . ?
C15 C14 H14 120.1(9) . . ?
C13 C14 H14 120.1(9) . . ?
C14 C15 C16 120.27(12) . . ?
C14 C15 H15 120.5(10) . . ?
C16 C15 H15 119.2(10) . . ?
C15 C16 C11 120.34(12) . . ?
C15 C16 H16 120.2(9) . . ?
C11 C16 H16 119.5(9) . . ?
N1 C17 H17C 109.0(8) . . ?
N1 C17 H17B 111.5(9) . . ?
H17C C17 H17B 110.0(12) . . ?
N1 C17 H17A 108.1(9) . . ?
H17C C17 H17A 108.5(12) . . ?
H17B C17 H17A 109.8(13) . . ?
C19 C18 C23 119.13(12) . . ?
C19 C18 N1 121.04(11) . . ?
C23 C18 N1 119.79(11) . . ?
C20 C19 C18 120.19(12) . . ?
C20 C19 H19 120.4(9) . . ?
C18 C19 H19 119.4(9) . . ?
C21 C20 C19 120.52(13) . . ?
C21 C20 H20 119.7(9) . . ?
C19 C20 H20 119.8(9) . . ?
C20 C21 C22 119.33(13) . . ?
C20 C21 H21 121.0(10) . . ?
C22 C21 H21 119.7(9) . . ?
C23 C22 C21 120.60(13) . . ?
C23 C22 H22 119.8(10) . . ?
C21 C22 H22 119.5(10) . . ?
C22 C23 C18 120.21(13) . . ?
C22 C23 H23 120.6(9) . . ?
C18 C23 H23 119.2(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_FO5017
_database_code_depnum_ccdc_archive 'CCDC 1426898'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N'
_chemical_formula_sum            'C24 H21 N'
_chemical_formula_weight         323.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   7.4316(1)
_cell_length_b                   23.6631(7)
_cell_length_c                   10.6845(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.375(2)
_cell_angle_gamma                90
_cell_volume                     1848.20(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.065
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10544
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4224
_reflns_number_gt                3444
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0298P)²+0.9168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4224
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0988
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.53188(15) 0.02853(5) 0.72301(11) 0.0225(3) Uani 1 1 d . . .
C1 C 0.58748(18) -0.02136(6) 0.78914(13) 0.0214(3) Uani 1 1 d . . .
C2 C 0.48503(19) -0.04514(6) 0.86799(13) 0.0235(3) Uani 1 1 d . . .
H2 H 0.382(2) -0.0239(7) 0.8874(16) 0.031(4) Uiso 1 1 d . . .
C3 C 0.51133(18) -0.09924(6) 0.92653(13) 0.0226(3) Uani 1 1 d . . .
C4 C 0.51962(18) -0.14387(6) 0.98119(13) 0.0231(3) Uani 1 1 d . . .
C5 C 0.53665(18) -0.19753(6) 1.04457(13) 0.0220(3) Uani 1 1 d . . .
C6 C 0.6609(2) -0.23764(6) 1.01573(14) 0.0284(3) Uani 1 1 d . . .
H6 H 0.734(2) -0.2283(7) 0.9524(16) 0.033(4) Uiso 1 1 d . . .
C7 C 0.6784(2) -0.28951(7) 1.07736(16) 0.0344(4) Uani 1 1 d . . .
H7 H 0.770(3) -0.3163(8) 1.0570(18) 0.048(5) Uiso 1 1 d . . .
C8 C 0.5740(2) -0.30187(7) 1.16835(15) 0.0339(4) Uani 1 1 d . . .
H8 H 0.588(2) -0.3378(8) 1.2127(17) 0.040(5) Uiso 1 1 d . . .
C9 C 0.4502(2) -0.26261(7) 1.19813(14) 0.0312(3) Uani 1 1 d . . .
H9 H 0.373(2) -0.2725(8) 1.2619(18) 0.042(5) Uiso 1 1 d . . .
C10 C 0.4306(2) -0.21064(6) 1.13649(14) 0.0265(3) Uani 1 1 d . . .
H10 H 0.343(2) -0.1829(8) 1.1549(17) 0.039(5) Uiso 1 1 d . . .
C11 C 0.75527(18) -0.04830(5) 0.75788(13) 0.0221(3) Uani 1 1 d . . .
C12 C 0.79233(19) -0.04634(6) 0.63416(14) 0.0244(3) Uani 1 1 d . . .
H12 H 0.707(2) -0.0271(7) 0.5668(17) 0.035(5) Uiso 1 1 d . . .
C13 C 0.9474(2) -0.07225(6) 0.60509(15) 0.0294(3) Uani 1 1 d . . .
H13 H 0.973(2) -0.0699(7) 0.5172(17) 0.034(4) Uiso 1 1 d . . .
C14 C 1.0678(2) -0.10034(7) 0.69949(16) 0.0325(3) Uani 1 1 d . . .
H14 H 1.175(2) -0.1178(7) 0.6786(16) 0.035(5) Uiso 1 1 d . . .
C15 C 1.0332(2) -0.10224(7) 0.82244(16) 0.0313(3) Uani 1 1 d . . .
H15 H 1.119(2) -0.1216(8) 0.8882(17) 0.037(5) Uiso 1 1 d . . .
C16 C 0.87862(19) -0.07597(6) 0.85196(15) 0.0261(3) Uani 1 1 d . . .
H16 H 0.854(2) -0.0766(7) 0.9377(16) 0.032(4) Uiso 1 1 d . . .
C17 C 0.34734(19) 0.04977(6) 0.72671(16) 0.0271(3) Uani 1 1 d . . .
H17C H 0.256(2) 0.0183(7) 0.7010(16) 0.030(4) Uiso 1 1 d . . .
H17B H 0.337(2) 0.0636(7) 0.8123(17) 0.030(4) Uiso 1 1 d . . .
H17A H 0.322(2) 0.0816(8) 0.6644(17) 0.036(5) Uiso 1 1 d . . .
C18 C 0.66482(18) 0.07110(6) 0.71187(13) 0.0214(3) Uani 1 1 d . . .
C19 C 0.6356(2) 0.10703(6) 0.60705(14) 0.0258(3) Uani 1 1 d . . .
H19 H 0.528(2) 0.1027(7) 0.5412(15) 0.027(4) Uiso 1 1 d . . .
C20 C 0.7577(2) 0.15020(6) 0.59672(14) 0.0267(3) Uani 1 1 d . . .
H20 H 0.735(2) 0.1755(7) 0.5225(16) 0.028(4) Uiso 1 1 d . . .
C21 C 0.91422(19) 0.15812(6) 0.68857(14) 0.0258(3) Uani 1 1 d . . .
C22 C 0.94497(19) 0.12122(6) 0.79141(14) 0.0246(3) Uani 1 1 d . . .
H22 H 1.055(2) 0.1268(7) 0.8590(16) 0.032(4) Uiso 1 1 d . . .
C23 C 0.82098(18) 0.07856(6) 0.80486(13) 0.0222(3) Uani 1 1 d . . .
H23 H 0.842(2) 0.0539(7) 0.8816(16) 0.032(4) Uiso 1 1 d . . .
C24 C 1.0418(3) 0.20658(9) 0.67743(19) 0.0425(4) Uani 1 1 d . . .
H24C H 1.171(3) 0.1957(10) 0.696(2) 0.067(7) Uiso 1 1 d . . .
H24B H 1.025(4) 0.2382(12) 0.740(3) 0.092(9) Uiso 1 1 d . . .
H24A H 1.013(3) 0.2235(10) 0.590(2) 0.066(7) Uiso 1 1 d . . .


_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 C1 1.3994(17) . ?
N1 C18 1.4310(17) . ?
N1 C17 1.4678(18) . ?
C1 C2 1.3553(19) . ?
C1 C11 1.4909(18) . ?
C2 C3 1.4229(19) . ?
C2 H2 0.969(17) . ?
C3 C4 1.2031(19) . ?
C4 C5 1.4338(19) . ?
C5 C6 1.3969(19) . ?
C5 C10 1.400(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.966(17) . ?
C7 C8 1.380(2) . ?
C7 H7 0.98(2) . ?
C8 C9 1.384(2) . ?
C8 H8 0.971(19) . ?
C9 C10 1.390(2) . ?
C9 H9 0.994(19) . ?
C10 H10 0.972(18) . ?
C11 C16 1.3956(19) . ?
C11 C12 1.399(2) . ?
C12 C13 1.389(2) . ?
C12 H12 0.982(18) . ?
C13 C14 1.391(2) . ?
C13 H13 0.994(18) . ?
C14 C15 1.384(2) . ?
C14 H14 0.957(17) . ?
C15 C16 1.392(2) . ?
C15 H15 0.974(18) . ?
C16 H16 0.966(17) . ?
C17 H17C 1.010(17) . ?
C17 H17B 0.988(17) . ?
C17 H17A 1.001(18) . ?
C18 C19 1.3916(19) . ?
C18 C23 1.3964(18) . ?
C19 C20 1.384(2) . ?
C19 H19 0.972(16) . ?
C20 C21 1.393(2) . ?
C20 H20 0.984(17) . ?
C21 C22 1.390(2) . ?
C21 C24 1.506(2) . ?
C22 C23 1.3916(19) . ?
C22 H22 0.997(17) . ?
C23 H23 0.995(17) . ?
C24 H24C 0.98(2) . ?
C24 H24B 1.03(3) . ?
C24 H24A 1.01(2) . ?

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
C1 N1 C18 119.37(11) . . ?
C1 N1 C17 117.88(11) . . ?
C18 N1 C17 115.06(11) . . ?
C2 C1 N1 121.07(12) . . ?
C2 C1 C11 123.22(12) . . ?
N1 C1 C11 115.49(11) . . ?
C1 C2 C3 126.78(13) . . ?
C1 C2 H2 118.1(10) . . ?
C3 C2 H2 115.1(10) . . ?
C4 C3 C2 173.87(14) . . ?
C3 C4 C5 177.59(14) . . ?
C6 C5 C10 118.83(13) . . ?
C6 C5 C4 120.20(13) . . ?
C10 C5 C4 120.97(12) . . ?
C7 C6 C5 120.34(14) . . ?
C7 C6 H6 121.3(10) . . ?
C5 C6 H6 118.4(10) . . ?
C8 C7 C6 120.35(15) . . ?
C8 C7 H7 121.3(11) . . ?
C6 C7 H7 118.3(11) . . ?
C7 C8 C9 120.07(14) . . ?
C7 C8 H8 120.5(11) . . ?
C9 C8 H8 119.4(11) . . ?
C8 C9 C10 120.13(15) . . ?
C8 C9 H9 119.3(11) . . ?
C10 C9 H9 120.6(11) . . ?
C9 C10 C5 120.28(14) . . ?
C9 C10 H10 121.2(11) . . ?
C5 C10 H10 118.5(11) . . ?
C16 C11 C12 118.73(13) . . ?
C16 C11 C1 120.43(13) . . ?
C12 C11 C1 120.84(12) . . ?
C13 C12 C11 120.61(13) . . ?
C13 C12 H12 119.5(10) . . ?
C11 C12 H12 119.9(10) . . ?
C12 C13 C14 120.01(14) . . ?
C12 C13 H13 119.8(10) . . ?
C14 C13 H13 120.2(10) . . ?
C15 C14 C13 119.91(14) . . ?
C15 C14 H14 120.8(10) . . ?
C13 C14 H14 119.3(10) . . ?
C14 C15 C16 120.17(14) . . ?
C14 C15 H15 119.4(10) . . ?
C16 C15 H15 120.5(10) . . ?
C15 C16 C11 120.55(14) . . ?
C15 C16 H16 120.8(10) . . ?
C11 C16 H16 118.7(10) . . ?
N1 C17 H17C 108.9(9) . . ?
N1 C17 H17B 111.6(10) . . ?
H17C C17 H17B 109.6(13) . . ?
N1 C17 H17A 107.9(10) . . ?
H17C C17 H17A 109.6(13) . . ?
H17B C17 H17A 109.2(14) . . ?
C19 C18 C23 118.99(12) . . ?
C19 C18 N1 119.15(12) . . ?
C23 C18 N1 121.84(12) . . ?
C20 C19 C18 120.38(13) . . ?
C20 C19 H19 119.1(10) . . ?
C18 C19 H19 120.5(10) . . ?
C19 C20 C21 121.30(13) . . ?
C19 C20 H20 119.8(9) . . ?
C21 C20 H20 118.9(9) . . ?
C22 C21 C20 118.04(13) . . ?
C22 C21 C24 121.63(14) . . ?
C20 C21 C24 120.30(14) . . ?
C21 C22 C23 121.31(13) . . ?
C21 C22 H22 119.1(10) . . ?
C23 C22 H22 119.5(10) . . ?
C22 C23 C18 119.94(13) . . ?
C22 C23 H23 120.1(10) . . ?
C18 C23 H23 119.9(10) . . ?
C21 C24 H24C 113.2(14) . . ?
C21 C24 H24B 110.7(15) . . ?
H24C C24 H24B 107(2) . . ?
C21 C24 H24A 110.3(13) . . ?
H24C C24 H24A 109.0(18) . . ?
H24B C24 H24A 107(2) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_FO5629
_database_code_depnum_ccdc_archive 'CCDC 1426899'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 F N'
_chemical_formula_sum            'C23 H18 F N'
_chemical_formula_weight         327.38

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.2846(1)
_cell_length_b                   23.2679(5)
_cell_length_c                   10.5794(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.835(1)
_cell_angle_gamma                90
_cell_volume                     1771.90(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.054
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7006
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12883
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         27.44
_reflns_number_total             4032
_reflns_number_gt                3744
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0303P)²+0.8103P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 1.05813(12) 0.71109(4) 0.20263(8) 0.0412(2) Uani 1 1 d . . .
N1 N 0.54183(12) 0.53733(4) 0.22022(8) 0.01875(19) Uani 1 1 d . . .
C1 C 0.59622(14) 0.48565(4) 0.28265(9) 0.0173(2) Uani 1 1 d . . .
C2 C 0.49073(15) 0.45973(5) 0.36132(10) 0.0193(2) Uani 1 1 d . . .
H2 H 0.384(2) 0.4801(6) 0.3810(13) 0.029(4) Uiso 1 1 d . . .
C3 C 0.52026(14) 0.40376(5) 0.41502(10) 0.0193(2) Uani 1 1 d . . .
C4 C 0.53578(14) 0.35728(5) 0.46550(10) 0.0192(2) Uani 1 1 d . . .
C5 C 0.56346(15) 0.30208(4) 0.52618(10) 0.0190(2) Uani 1 1 d . . .
C6 C 0.70141(16) 0.26499(5) 0.49463(11) 0.0243(2) Uani 1 1 d . . .
H6 H 0.779(2) 0.2771(6) 0.4296(14) 0.032(4) Uiso 1 1 d . . .
C7 C 0.73023(19) 0.21210(5) 0.55476(12) 0.0302(3) Uani 1 1 d . . .
H7 H 0.827(2) 0.1864(7) 0.5318(15) 0.040(4) Uiso 1 1 d . . .
C8 C 0.6238(2) 0.19537(5) 0.64640(11) 0.0311(3) Uani 1 1 d . . .
H8 H 0.648(2) 0.1585(7) 0.6876(14) 0.036(4) Uiso 1 1 d . . .
C9 C 0.48639(18) 0.23173(5) 0.67770(11) 0.0282(3) Uani 1 1 d . . .
H9 H 0.411(2) 0.2195(7) 0.7413(15) 0.036(4) Uiso 1 1 d . . .
C10 C 0.45574(16) 0.28480(5) 0.61825(11) 0.0232(2) Uani 1 1 d . . .
H10 H 0.3587(19) 0.3109(6) 0.6401(13) 0.028(3) Uiso 1 1 d . . .
C11 C 0.76794(14) 0.45870(4) 0.24866(10) 0.0176(2) Uani 1 1 d . . .
C12 C 0.80377(15) 0.45980(5) 0.12255(10) 0.0205(2) Uani 1 1 d . . .
H12 H 0.7175(19) 0.4790(6) 0.0560(13) 0.025(3) Uiso 1 1 d . . .
C13 C 0.96100(16) 0.43265(5) 0.09057(11) 0.0238(2) Uani 1 1 d . . .
H13 H 0.9852(19) 0.4338(6) 0.0025(14) 0.026(3) Uiso 1 1 d . . .
C14 C 1.08318(16) 0.40425(5) 0.18383(12) 0.0254(2) Uani 1 1 d . . .
H14 H 1.193(2) 0.3847(6) 0.1612(13) 0.030(4) Uiso 1 1 d . . .
C15 C 1.04898(15) 0.40320(5) 0.30940(11) 0.0247(2) Uani 1 1 d . . .
H15 H 1.135(2) 0.3835(6) 0.3754(14) 0.031(4) Uiso 1 1 d . . .
C16 C 0.89319(15) 0.43076(5) 0.34193(11) 0.0209(2) Uani 1 1 d . . .
H16 H 0.8691(19) 0.4312(6) 0.4304(13) 0.026(3) Uiso 1 1 d . . .
C17 C 0.35448(15) 0.55896(5) 0.22745(11) 0.0224(2) Uani 1 1 d . . .
H17C H 0.262(2) 0.5282(6) 0.1999(13) 0.030(4) Uiso 1 1 d . . .
H17B H 0.3414(19) 0.5725(6) 0.3159(13) 0.025(3) Uiso 1 1 d . . .
H17A H 0.3281(19) 0.5919(6) 0.1680(13) 0.025(3) Uiso 1 1 d . . .
C18 C 0.67939(14) 0.58094(4) 0.21585(10) 0.0181(2) Uani 1 1 d . . .
C19 C 0.65812(16) 0.61959(5) 0.11387(10) 0.0227(2) Uani 1 1 d . . .
H19 H 0.552(2) 0.6156(6) 0.0448(13) 0.027(3) Uiso 1 1 d . . .
C20 C 0.78465(18) 0.66389(5) 0.10945(11) 0.0266(2) Uani 1 1 d . . .
H20 H 0.769(2) 0.6918(7) 0.0396(15) 0.036(4) Uiso 1 1 d . . .
C21 C 0.93374(17) 0.66803(5) 0.20667(11) 0.0261(2) Uani 1 1 d . . .
C22 C 0.96088(15) 0.63028(5) 0.30834(11) 0.0234(2) Uani 1 1 d . . .
H22 H 1.068(2) 0.6357(6) 0.3748(14) 0.030(4) Uiso 1 1 d . . .
C23 C 0.83097(15) 0.58676(5) 0.31338(10) 0.0200(2) Uani 1 1 d . . .
H23 H 0.8442(19) 0.5602(6) 0.3864(13) 0.026(3) Uiso 1 1 d . . .


_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
F1 C21 1.3560(13) . ?
N1 C1 1.3997(13) . ?
N1 C18 1.4319(13) . ?
N1 C17 1.4676(13) . ?
C1 C2 1.3577(15) . ?
C1 C11 1.4918(14) . ?
C2 C3 1.4237(15) . ?
C2 H2 0.962(14) . ?
C3 C4 1.2040(15) . ?
C4 C5 1.4361(14) . ?
C5 C10 1.4004(15) . ?
C5 C6 1.4032(15) . ?
C6 C7 1.3864(17) . ?
C6 H6 0.993(15) . ?
C7 C8 1.3871(19) . ?
C7 H7 0.980(16) . ?
C8 C9 1.3889(19) . ?
C8 H8 0.966(16) . ?
C9 C10 1.3881(16) . ?
C9 H9 0.973(15) . ?
C10 H10 0.985(14) . ?
C11 C16 1.3972(15) . ?
C11 C12 1.3986(15) . ?
C12 C13 1.3943(15) . ?
C12 H12 0.977(14) . ?
C13 C14 1.3902(17) . ?
C13 H13 0.975(14) . ?
C14 C15 1.3889(17) . ?
C14 H14 0.979(15) . ?
C15 C16 1.3919(16) . ?
C15 H15 0.978(15) . ?
C16 H16 0.978(14) . ?
C17 H17C 0.993(15) . ?
C17 H17B 1.006(14) . ?
C17 H17A 0.992(14) . ?
C18 C19 1.3947(15) . ?
C18 C23 1.3971(15) . ?
C19 C20 1.3884(16) . ?
C19 H19 0.985(14) . ?
C20 C21 1.3797(17) . ?
C20 H20 0.976(16) . ?
C21 C22 1.3792(17) . ?
C22 C23 1.3925(15) . ?
C22 H22 0.975(15) . ?
C23 H23 0.983(14) . ?

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
C1 N1 C18 118.38(8) . . ?
C1 N1 C17 117.92(9) . . ?
C18 N1 C17 114.81(8) . . ?
C2 C1 N1 121.68(9) . . ?
C2 C1 C11 122.38(9) . . ?
N1 C1 C11 115.75(9) . . ?
C1 C2 C3 125.86(10) . . ?
C1 C2 H2 117.9(8) . . ?
C3 C2 H2 116.2(8) . . ?
C4 C3 C2 175.45(11) . . ?
C3 C4 C5 177.34(11) . . ?
C10 C5 C6 119.16(10) . . ?
C10 C5 C4 120.83(10) . . ?
C6 C5 C4 120.01(10) . . ?
C7 C6 C5 120.02(11) . . ?
C7 C6 H6 120.5(9) . . ?
C5 C6 H6 119.5(8) . . ?
C6 C7 C8 120.55(11) . . ?
C6 C7 H7 119.4(9) . . ?
C8 C7 H7 120.0(9) . . ?
C7 C8 C9 119.76(11) . . ?
C7 C8 H8 118.7(9) . . ?
C9 C8 H8 121.6(9) . . ?
C10 C9 C8 120.37(11) . . ?
C10 C9 H9 120.3(9) . . ?
C8 C9 H9 119.4(9) . . ?
C9 C10 C5 120.14(11) . . ?
C9 C10 H10 120.8(8) . . ?
C5 C10 H10 119.0(8) . . ?
C16 C11 C12 119.01(10) . . ?
C16 C11 C1 120.41(9) . . ?
C12 C11 C1 120.57(9) . . ?
C13 C12 C11 120.25(10) . . ?
C13 C12 H12 119.6(8) . . ?
C11 C12 H12 120.2(8) . . ?
C14 C13 C12 120.22(11) . . ?
C14 C13 H13 120.1(8) . . ?
C12 C13 H13 119.7(8) . . ?
C15 C14 C13 119.85(10) . . ?
C15 C14 H14 119.9(8) . . ?
C13 C14 H14 120.3(8) . . ?
C14 C15 C16 120.08(10) . . ?
C14 C15 H15 120.0(8) . . ?
C16 C15 H15 119.9(8) . . ?
C15 C16 C11 120.57(10) . . ?
C15 C16 H16 121.0(8) . . ?
C11 C16 H16 118.5(8) . . ?
N1 C17 H17C 109.2(8) . . ?
N1 C17 H17B 112.2(8) . . ?
H17C C17 H17B 110.0(11) . . ?
N1 C17 H17A 108.9(8) . . ?
H17C C17 H17A 108.4(11) . . ?
H17B C17 H17A 108.0(11) . . ?
C19 C18 C23 119.35(10) . . ?
C19 C18 N1 119.12(9) . . ?
C23 C18 N1 121.50(9) . . ?
C20 C19 C18 120.62(11) . . ?
C20 C19 H19 119.7(8) . . ?
C18 C19 H19 119.6(8) . . ?
C21 C20 C19 118.51(11) . . ?
C21 C20 H20 120.4(9) . . ?
C19 C20 H20 121.1(9) . . ?
F1 C21 C20 118.77(11) . . ?
F1 C21 C22 118.60(11) . . ?
C20 C21 C22 122.62(11) . . ?
C21 C22 C23 118.43(11) . . ?
C21 C22 H22 118.9(9) . . ?
C23 C22 H22 122.6(9) . . ?
C22 C23 C18 120.45(10) . . ?
C22 C23 H23 120.2(8) . . ?
C18 C23 H23 119.4(8) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.44
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_FO4926
_database_code_depnum_ccdc_archive 'CCDC 1426900'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H28 N2'
_chemical_formula_sum            'C30 H28 N2'
_chemical_formula_weight         416.54

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   10.5309(15)
_cell_length_b                   11.255(2)
_cell_length_c                   10.6349(17)
_cell_angle_alpha                90
_cell_angle_beta                 113.94(1)
_cell_angle_gamma                90.00
_cell_volume                     1152.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.086
_exptl_crystal_size_mid          0.076
_exptl_crystal_size_min          0.076
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             444
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5072
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7660
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_sigmaI/netI    0.0692
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.77
_diffrn_reflns_theta_max         27.10
_reflns_number_total             2507
_reflns_number_gt                1700
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0428P)²+1.0579P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2507
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1573
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.4455(2) -0.00104(19) 0.2639(2) 0.0307(5) Uani 1 1 d . . .
C1 C 0.4573(2) -0.0504(2) 0.1469(3) 0.0290(6) Uani 1 1 d . . .
C2 C 0.4813(3) 0.0196(3) 0.0545(3) 0.0313(6) Uani 1 1 d . . .
H2 H 0.472(3) 0.111(3) 0.063(3) 0.052(9) Uiso 1 1 d . . .
C3 C 0.3253(3) -0.0357(3) 0.2913(3) 0.0389(7) Uani 1 1 d . . .
H3A H 0.303(3) -0.122(3) 0.263(3) 0.058(10) Uiso 1 1 d . . .
H3B H 0.243(3) 0.007(3) 0.237(3) 0.041(8) Uiso 1 1 d . . .
H3C H 0.340(3) -0.026(2) 0.389(3) 0.036(8) Uiso 1 1 d . . .
C4 C 0.5087(3) 0.1094(2) 0.3187(2) 0.0300(6) Uani 1 1 d . . .
C5 C 0.4412(3) 0.1949(3) 0.3631(3) 0.0379(7) Uani 1 1 d . . .
H5 H 0.347(3) 0.179(3) 0.357(3) 0.040(8) Uiso 1 1 d . . .
C6 C 0.5102(3) 0.2997(3) 0.4240(3) 0.0439(8) Uani 1 1 d . . .
H6 H 0.454(3) 0.358(3) 0.454(3) 0.059(10) Uiso 1 1 d . . .
C7 C 0.6451(3) 0.3195(3) 0.4420(3) 0.0448(8) Uani 1 1 d . . .
H7 H 0.692(3) 0.392(3) 0.481(3) 0.057(10) Uiso 1 1 d . . .
C8 C 0.7131(3) 0.2346(3) 0.3973(3) 0.0391(7) Uani 1 1 d . . .
H8 H 0.809(3) 0.248(3) 0.402(3) 0.046(8) Uiso 1 1 d . . .
C9 C 0.6459(3) 0.1312(3) 0.3362(3) 0.0346(6) Uani 1 1 d . . .
H9 H 0.694(3) 0.075(3) 0.304(3) 0.037(8) Uiso 1 1 d . . .
C10 C 0.4494(2) -0.1820(2) 0.1383(3) 0.0316(6) Uani 1 1 d . . .
C11 C 0.3728(3) -0.2389(3) 0.0134(3) 0.0392(7) Uani 1 1 d . . .
H11 H 0.317(3) -0.188(3) -0.067(3) 0.050(9) Uiso 1 1 d . . .
C12 C 0.3704(3) -0.3618(3) 0.0049(4) 0.0485(8) Uani 1 1 d . . .
H12 H 0.311(4) -0.404(3) -0.087(4) 0.078(12) Uiso 1 1 d . . .
C13 C 0.4414(3) -0.4299(3) 0.1184(4) 0.0490(8) Uani 1 1 d . . .
H13 H 0.447(4) -0.517(4) 0.120(4) 0.076(12) Uiso 1 1 d . . .
C14 C 0.5161(3) -0.3752(3) 0.2445(4) 0.0455(8) Uani 1 1 d . . .
H14 H 0.563(3) -0.419(3) 0.325(3) 0.041(8) Uiso 1 1 d . . .
C15 C 0.5189(3) -0.2515(3) 0.2547(3) 0.0356(6) Uani 1 1 d . . .
H15 H 0.569(3) -0.213(2) 0.347(3) 0.030(7) Uiso 1 1 d . . .


_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 C1 1.414(3) . ?
N1 C4 1.419(3) . ?
N1 C3 1.462(3) . ?
C1 C2 1.360(4) . ?
C1 C10 1.483(4) . ?
C2 C2 1.438(5) 3_655 ?
C2 H2 1.04(3) . ?
C3 H3A 1.02(4) . ?
C3 H3B 0.95(3) . ?
C3 H3C 0.99(3) . ?
C4 C5 1.388(4) . ?
C4 C9 1.402(4) . ?
C5 C6 1.398(4) . ?
C5 H5 0.99(3) . ?
C6 C7 1.373(4) . ?
C6 H6 1.02(3) . ?
C7 C8 1.389(4) . ?
C7 H7 0.96(3) . ?
C8 C9 1.380(4) . ?
C8 H8 1.00(3) . ?
C9 H9 0.95(3) . ?
C10 C15 1.394(4) . ?
C10 C11 1.399(4) . ?
C11 C12 1.386(4) . ?
C11 H11 1.00(3) . ?
C12 C13 1.368(5) . ?
C12 H12 1.03(4) . ?
C13 C14 1.393(5) . ?
C13 H13 0.98(4) . ?
C14 C15 1.396(4) . ?
C14 H14 0.94(3) . ?
C15 H15 1.01(3) . ?

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
C1 N1 C4 120.8(2) . . ?
C1 N1 C3 117.6(2) . . ?
C4 N1 C3 116.9(2) . . ?
C2 C1 N1 121.1(2) . . ?
C2 C1 C10 123.8(2) . . ?
N1 C1 C10 115.1(2) . . ?
C1 C2 C2 126.6(3) . 3_655 ?
C1 C2 H2 117.2(17) . . ?
C2 C2 H2 116.1(17) 3_655 . ?
N1 C3 H3A 108.3(18) . . ?
N1 C3 H3B 113.2(17) . . ?
H3A C3 H3B 105(3) . . ?
N1 C3 H3C 113.3(16) . . ?
H3A C3 H3C 109(2) . . ?
H3B C3 H3C 108(2) . . ?
C5 C4 C9 118.4(3) . . ?
C5 C4 N1 121.8(2) . . ?
C9 C4 N1 119.7(2) . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 119.3(17) . . ?
C6 C5 H5 120.5(17) . . ?
C7 C6 C5 121.0(3) . . ?
C7 C6 H6 123.5(19) . . ?
C5 C6 H6 115.4(19) . . ?
C6 C7 C8 119.3(3) . . ?
C6 C7 H7 122(2) . . ?
C8 C7 H7 119(2) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 117.9(18) . . ?
C7 C8 H8 121.7(18) . . ?
C8 C9 C4 121.0(3) . . ?
C8 C9 H9 119.0(17) . . ?
C4 C9 H9 120.0(17) . . ?
C15 C10 C11 118.6(3) . . ?
C15 C10 C1 120.6(2) . . ?
C11 C10 C1 120.8(3) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 121.6(18) . . ?
C10 C11 H11 117.8(18) . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119(2) . . ?
C11 C12 H12 120(2) . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 126(2) . . ?
C14 C13 H13 115(2) . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 122.0(19) . . ?
C15 C14 H14 117.8(19) . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 H15 120.4(15) . . ?
C14 C15 H15 119.3(15) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_FO5419
_database_code_depnum_ccdc_archive 'CCDC 1426901'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H26 F2 N2'
_chemical_formula_sum            'C30 H26 F2 N2'
_chemical_formula_weight         452.53

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.0689(3)
_cell_length_b                   12.6418(4)
_cell_length_c                   8.3768(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.224(2)
_cell_angle_gamma                90
_cell_volume                     1145.60(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.058
_exptl_crystal_size_mid          0.046
_exptl_crystal_size_min          0.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             476
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5222
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6189
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0285
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.88
_diffrn_reflns_theta_max         25.68
_reflns_number_total             2173
_reflns_number_gt                1963
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0667P)²+1.3713P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2173
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0704
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1838
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.94889(16) 0.86922(14) 0.1380(3) 0.0536(6) Uani 1 1 d . . .
N1 N 0.7323(2) 0.47538(17) 0.0048(3) 0.0281(5) Uani 1 1 d . . .
C1 C 0.6202(2) 0.46136(19) -0.1146(3) 0.0258(6) Uani 1 1 d . . .
C2 C 0.5094(2) 0.48238(19) -0.0781(3) 0.0250(6) Uani 1 1 d . . .
H2 H 0.438(3) 0.477(2) -0.161(3) 0.019(7) Uiso 1 1 d . . .
C3 C 0.8100(3) 0.3821(2) 0.0488(4) 0.0335(7) Uani 1 1 d . . .
H3A H 0.8263 0.3719 0.1674 0.041(9) Uiso 1 1 calc R . .
H3B H 0.8884 0.3919 0.0141 0.031(8) Uiso 1 1 calc R . .
H3C H 0.7675 0.3197 -0.0057 0.054(10) Uiso 1 1 calc R . .
C4 C 0.7837(2) 0.5754(2) 0.0427(3) 0.0255(6) Uani 1 1 d . . .
C5 C 0.7281(3) 0.6671(2) -0.0322(4) 0.0331(7) Uani 1 1 d . . .
H5 H 0.652(3) 0.660(3) -0.107(4) 0.043(9) Uiso 1 1 d . . .
C6 C 0.7830(3) 0.7650(2) 0.0003(4) 0.0385(7) Uani 1 1 d . . .
H6 H 0.743(3) 0.828(3) -0.057(4) 0.038(9) Uiso 1 1 d . . .
C7 C 0.8939(3) 0.7720(2) 0.1104(4) 0.0367(7) Uani 1 1 d . . .
C8 C 0.9503(3) 0.6854(2) 0.1903(4) 0.0380(7) Uani 1 1 d . . .
H8 H 1.028(3) 0.691(3) 0.276(4) 0.043(9) Uiso 1 1 d . . .
C9 C 0.8960(3) 0.5864(2) 0.1572(4) 0.0325(7) Uani 1 1 d . . .
H9 H 0.937(3) 0.523(3) 0.207(4) 0.041(9) Uiso 1 1 d . . .
C10 C 0.6312(2) 0.4247(2) -0.2783(3) 0.0262(6) Uani 1 1 d . . .
C11 C 0.5377(3) 0.3656(2) -0.3766(3) 0.0293(6) Uani 1 1 d . . .
H11 H 0.466(3) 0.346(2) -0.331(4) 0.026(7) Uiso 1 1 d . . .
C12 C 0.5459(3) 0.3357(2) -0.5330(4) 0.0337(7) Uani 1 1 d . . .
H12 H 0.478(3) 0.296(3) -0.603(4) 0.034(8) Uiso 1 1 d . . .
C13 C 0.6482(3) 0.3644(2) -0.5946(4) 0.0356(7) Uani 1 1 d . . .
H13 H 0.657(3) 0.342(3) -0.703(4) 0.034(8) Uiso 1 1 d . . .
C14 C 0.7430(3) 0.4218(2) -0.4973(4) 0.0358(7) Uani 1 1 d . . .
H14 H 0.819(4) 0.442(3) -0.534(5) 0.067(12) Uiso 1 1 d . . .
C15 C 0.7355(3) 0.4512(2) -0.3408(4) 0.0317(6) Uani 1 1 d . . .
H15 H 0.802(3) 0.490(3) -0.274(4) 0.037(8) Uiso 1 1 d . . .


_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
F1 C7 1.370(3) . ?
N1 C4 1.395(3) . ?
N1 C1 1.431(3) . ?
N1 C3 1.460(3) . ?
C1 C2 1.351(4) . ?
C1 C10 1.477(4) . ?
C2 C2 1.438(5) 3_665 ?
C2 H2 0.94(3) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.397(4) . ?
C4 C9 1.407(4) . ?
C5 C6 1.381(4) . ?
C5 H5 0.94(4) . ?
C6 C7 1.372(4) . ?
C6 H6 0.99(3) . ?
C7 C8 1.364(4) . ?
C8 C9 1.390(4) . ?
C8 H8 1.00(4) . ?
C9 H9 0.97(4) . ?
C10 C11 1.396(4) . ?
C10 C15 1.405(4) . ?
C11 C12 1.385(4) . ?
C11 H11 0.98(3) . ?
C12 C13 1.388(4) . ?
C12 H12 0.99(3) . ?
C13 C14 1.389(5) . ?
C13 H13 0.98(3) . ?
C14 C15 1.382(4) . ?
C14 H14 0.98(4) . ?
C15 H15 0.96(3) . ?

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
C4 N1 C1 121.5(2) . . ?
C4 N1 C3 119.0(2) . . ?
C1 N1 C3 117.0(2) . . ?
C2 C1 N1 120.8(2) . . ?
C2 C1 C10 122.0(2) . . ?
N1 C1 C10 117.2(2) . . ?
C1 C2 C2 125.5(3) . 3_665 ?
C1 C2 H2 118.7(16) . . ?
C2 C2 H2 115.7(16) 3_665 . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 C5 122.0(2) . . ?
N1 C4 C9 120.2(2) . . ?
C5 C4 C9 117.7(2) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 121(2) . . ?
C4 C5 H5 118(2) . . ?
C7 C6 C5 119.0(3) . . ?
C7 C6 H6 121.2(19) . . ?
C5 C6 H6 119.8(19) . . ?
C8 C7 F1 119.7(3) . . ?
C8 C7 C6 122.0(3) . . ?
F1 C7 C6 118.3(3) . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H8 122(2) . . ?
C9 C8 H8 119(2) . . ?
C8 C9 C4 120.5(3) . . ?
C8 C9 H9 121(2) . . ?
C4 C9 H9 119(2) . . ?
C11 C10 C15 118.3(3) . . ?
C11 C10 C1 121.3(2) . . ?
C15 C10 C1 120.5(2) . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 121.4(17) . . ?
C10 C11 H11 117.6(17) . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 120.4(19) . . ?
C13 C12 H12 119.4(18) . . ?
C14 C13 C12 119.5(3) . . ?
C14 C13 H13 118.9(19) . . ?
C12 C13 H13 121.6(19) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 H14 117(2) . . ?
C13 C14 H14 123(2) . . ?
C14 C15 C10 120.5(3) . . ?
C14 C15 H15 120(2) . . ?
C10 C15 H15 119(2) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.059
####################################################################### 
# 
# 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_FO5630
_database_code_depnum_ccdc_archive 'CCDC 1426902'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H27 F N2'
_chemical_formula_sum            'C30 H27 F N2'
_chemical_formula_weight         434.54

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.7393(4)
_cell_length_b                   8.3583(3)
_cell_length_c                   11.9106(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.576(2)
_cell_angle_gamma                90
_cell_volume                     1148.82(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.042
_exptl_crystal_size_mid          0.038
_exptl_crystal_size_min          0.028
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker-AXS, 2002'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      133(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'phi- + omega-scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7762
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_sigmaI/netI    0.0307
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.50
_reflns_number_total             2618
_reflns_number_gt                2346
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       COLLECT
_computing_cell_refinement       DENZO
_computing_data_reduction        DENZO
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXTL/PC
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 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 > 2sigma(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)+(0.0716P)²+1.1608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2618
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0671
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1778
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_restrained_S_all      1.159
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.78383(14) 0.4321(2) 0.45055(14) 0.0228(4) Uani 1 1 d . . .
C1 C 0.88809(16) 0.3499(2) 0.44009(16) 0.0212(4) Uani 1 1 d . . .
C2 C 0.99189(17) 0.4192(2) 0.47857(17) 0.0232(4) Uani 1 1 d . . .
H2 H 1.062(2) 0.355(3) 0.482(2) 0.021(6) Uiso 1 1 d . . .
C3 C 0.7554(2) 0.4508(3) 0.56385(19) 0.0335(5) Uani 1 1 d . . .
H3C H 0.821(2) 0.411(3) 0.623(2) 0.038(7) Uiso 1 1 d . . .
H3B H 0.685(3) 0.399(4) 0.569(3) 0.061(10) Uiso 1 1 d . . .
H3A H 0.740(3) 0.564(4) 0.584(3) 0.049(8) Uiso 1 1 d . . .
C4 C 0.70634(17) 0.4847(2) 0.35495(16) 0.0214(4) Uani 1 1 d . A .
C5 C 0.73135(18) 0.4673(3) 0.24449(18) 0.0247(4) Uani 1 1 d . . .
H5 H 0.803(2) 0.415(4) 0.235(2) 0.042(8) Uiso 1 1 d . . .
C6 C 0.65842(19) 0.5303(3) 0.15012(19) 0.0301(5) Uani 1 1 d . A .
H6 H 0.677(3) 0.522(4) 0.076(3) 0.044(8) Uiso 1 1 d . . .
F1 F 0.4964(2) 0.6815(4) 0.0691(2) 0.0406(7) Uani 0.50 1 d P A 1
C7 C 0.55907(19) 0.6103(3) 0.1634(2) 0.0326(5) Uani 1 1 d . . .
H7A H 0.5102 0.6553 0.0987 0.039 Uiso 0.50 1 calc PR A 2
C8 C 0.53009(18) 0.6254(3) 0.2703(2) 0.0309(5) Uani 1 1 d . A .
H8 H 0.459(2) 0.683(4) 0.277(2) 0.042(8) Uiso 1 1 d . . .
C9 C 0.60222(17) 0.5628(3) 0.36550(19) 0.0257(5) Uani 1 1 d . . .
H9 H 0.583(2) 0.575(3) 0.441(2) 0.034(7) Uiso 1 1 d . . .
C10 C 0.87718(17) 0.1837(2) 0.39635(16) 0.0215(4) Uani 1 1 d . . .
C11 C 0.96991(18) 0.1004(3) 0.36519(17) 0.0243(4) Uani 1 1 d . . .
H11 H 1.049(2) 0.155(3) 0.368(2) 0.028(6) Uiso 1 1 d . . .
C12 C 0.9578(2) -0.0594(3) 0.33214(18) 0.0276(5) Uani 1 1 d . . .
H12 H 1.028(2) -0.112(3) 0.316(2) 0.035(7) Uiso 1 1 d . . .
C13 C 0.8532(2) -0.1376(3) 0.32685(18) 0.0279(5) Uani 1 1 d . . .
H13 H 0.846(2) -0.248(4) 0.306(2) 0.037(7) Uiso 1 1 d . . .
C14 C 0.7595(2) -0.0560(3) 0.35415(19) 0.0289(5) Uani 1 1 d . . .
H14 H 0.682(3) -0.104(4) 0.347(2) 0.041(7) Uiso 1 1 d . . .
C15 C 0.77114(18) 0.1033(3) 0.38847(17) 0.0250(4) Uani 1 1 d . . .
H15 H 0.706(2) 0.156(3) 0.408(2) 0.036(7) Uiso 1 1 d . . .


_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 C4 1.392(3) . ?
N1 C1 1.429(2) . ?
N1 C3 1.457(3) . ?
C1 C2 1.351(3) . ?
C1 C10 1.481(3) . ?
C2 C2 1.443(4) 3_766 ?
C2 H2 0.98(2) . ?
C3 H3C 1.00(3) . ?
C3 H3B 0.95(4) . ?
C3 H3A 1.00(3) . ?
C4 C5 1.407(3) . ?
C4 C9 1.412(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.98(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.95(3) . ?
F1 C7 1.362(3) . ?
C7 C8 1.383(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8 0.99(3) . ?
C9 H9 0.98(3) . ?
C10 C11 1.399(3) . ?
C10 C15 1.402(3) . ?
C11 C12 1.392(3) . ?
C11 H11 1.03(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.98(3) . ?
C13 C14 1.383(3) . ?
C13 H13 0.95(3) . ?
C14 C15 1.392(3) . ?
C14 H14 0.99(3) . ?
C15 H15 0.95(3) . ?

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
C4 N1 C1 121.48(16) . . ?
C4 N1 C3 119.83(17) . . ?
C1 N1 C3 118.56(17) . . ?
C2 C1 N1 119.84(18) . . ?
C2 C1 C10 122.43(18) . . ?
N1 C1 C10 117.49(17) . . ?
C1 C2 C2 125.0(2) . 3_766 ?
C1 C2 H2 119.0(14) . . ?
C2 C2 H2 115.9(14) 3_766 . ?
N1 C3 H3C 109.9(16) . . ?
N1 C3 H3B 111(2) . . ?
H3C C3 H3B 112(3) . . ?
N1 C3 H3A 114.1(18) . . ?
H3C C3 H3A 107(2) . . ?
H3B C3 H3A 102(3) . . ?
N1 C4 C5 121.01(18) . . ?
N1 C4 C9 121.32(18) . . ?
C5 C4 C9 117.62(19) . . ?
C6 C5 C4 121.02(19) . . ?
C6 C5 H5 119.5(17) . . ?
C4 C5 H5 119.4(17) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.2(18) . . ?
C5 C6 H6 120.7(18) . . ?
F1 C7 C6 117.3(2) . . ?
F1 C7 C8 122.1(2) . . ?
C6 C7 C8 120.4(2) . . ?
F1 C7 H7A 4.5 . . ?
C6 C7 H7A 119.8 . . ?
C8 C7 H7A 119.8 . . ?
C7 C8 C9 120.1(2) . . ?
C7 C8 H8 118.8(17) . . ?
C9 C8 H8 121.1(17) . . ?
C8 C9 C4 120.7(2) . . ?
C8 C9 H9 120.5(16) . . ?
C4 C9 H9 118.7(16) . . ?
C11 C10 C15 117.93(18) . . ?
C11 C10 C1 122.63(18) . . ?
C15 C10 C1 119.42(18) . . ?
C12 C11 C10 120.59(19) . . ?
C12 C11 H11 118.5(14) . . ?
C10 C11 H11 120.9(14) . . ?
C13 C12 C11 120.6(2) . . ?
C13 C12 H12 123.1(16) . . ?
C11 C12 H12 116.2(16) . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2(17) . . ?
C12 C13 H13 120.1(17) . . ?
C13 C14 C15 120.1(2) . . ?
C13 C14 H14 122.9(17) . . ?
C15 C14 H14 117.0(17) . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 H15 118.4(17) . . ?
C10 C15 H15 120.5(17) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.066
