# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1409623'
_audit_update_record             
;
2015-09-05 deposited with the CCDC.
2015-09-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 F N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         344.42

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_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                   23.8959(8)
_cell_length_b                   5.8737(2)
_cell_length_c                   27.3670(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.5789(13)
_cell_angle_gamma                90
_cell_volume                     3571.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6924
_cell_measurement_theta_min      2.8680
_cell_measurement_theta_max      30.3326
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456

_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      103.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            41456
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_theta_min         1.42
_diffrn_reflns_theta_max         30.58
_diffrn_reflns_theta_full        30.58
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38

_refine_special_details          
;
;

_reflns_number_total             10964
_reflns_number_gt                7902
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_gt          0.1238
_refine_ls_wR_factor_ref         0.1447
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_number_reflns         10964
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+1.1720P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.336
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'

_computing_data_collection       'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2014)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.34077(6) 0.3988(2) 0.12637(5) 0.0148(3) Uani d . . . 1 . .
C C2 0.26198(7) 0.6356(3) 0.12115(6) 0.0205(3) Uani d . . . 1 . .
H H2A 0.2674 0.8002 0.1166 0.025 Uiso calc U . R 1 . .
H H2B 0.2286 0.6142 0.1339 0.025 Uiso calc U . R 1 . .
C C3 0.25067(6) 0.5033(2) 0.06978(6) 0.0152(3) Uani d . . . 1 . .
H H3 0.2425 0.6144 0.0403 0.018 Uiso calc U . R 1 . .
C C4 0.19734(6) 0.3369(2) 0.05645(5) 0.0152(3) Uani d . . . 1 . .
C C5 0.19110(7) 0.1874(3) 0.00976(6) 0.0225(3) Uani d . . . 1 . .
H H5A 0.1576 0.081 0.0037 0.034 Uiso calc U . R 1 . .
H H5B 0.2284 0.1016 0.0168 0.034 Uiso calc U . R 1 . .
H H5C 0.1832 0.2826 -0.0215 0.034 Uiso calc U . R 1 . .
C C6 0.13985(6) 0.4644(2) 0.04966(5) 0.0144(3) Uani d . . . 1 . .
C C7 0.11788(7) 0.6228(2) 0.00908(6) 0.0198(3) Uani d . . . 1 . .
H H7 0.1383 0.6458 -0.0145 0.024 Uiso calc U . R 1 . .
C C8 0.06647(7) 0.7468(3) 0.00296(7) 0.0270(4) Uani d . . . 1 . .
H H8 0.0518 0.8544 -0.0248 0.032 Uiso calc U . R 1 . .
C C9 0.03635(7) 0.7150(3) 0.03698(7) 0.0278(4) Uani d . . . 1 . .
H H9 0.0015 0.8024 0.0331 0.033 Uiso calc U . R 1 . .
C C10 0.05714(7) 0.5556(3) 0.07670(6) 0.0245(3) Uani d . . . 1 . .
H H10 0.0362 0.5319 0.0998 0.029 Uiso calc U . R 1 . .
C C11 0.10860(7) 0.4297(3) 0.08301(6) 0.0201(3) Uani d . . . 1 . .
H H11 0.1225 0.3194 0.1102 0.024 Uiso calc U . R 1 . .
C C12 0.40257(6) 0.3062(2) 0.14923(6) 0.0155(3) Uani d . . . 1 . .
C C13 0.41663(7) 0.0987(3) 0.13177(6) 0.0204(3) Uani d . . . 1 . .
H H13 0.3865 0.0159 0.105 0.024 Uiso calc U . R 1 . .
C C14 0.47489(7) 0.0134(3) 0.15364(6) 0.0250(3) Uani d . . . 1 . .
H H14 0.4844 -0.1286 0.142 0.03 Uiso calc U . R 1 . .
C C15 0.51916(7) 0.1344(3) 0.19236(6) 0.0247(3) Uani d . . . 1 . .
H H15 0.5589 0.0752 0.2071 0.03 Uiso calc U . R 1 . .
C C16 0.50550(7) 0.3417(3) 0.20955(6) 0.0224(3) Uani d . . . 1 . .
H H16 0.5359 0.4251 0.2359 0.027 Uiso calc U . R 1 . .
C C17 0.44730(6) 0.4273(2) 0.18807(6) 0.0177(3) Uani d . . . 1 . .
H H17 0.438 0.5691 0.1999 0.021 Uiso calc U . R 1 . .
C C18 0.32584(6) 0.4893(2) 0.21011(6) 0.0150(3) Uani d . . . 1 . .
C C19 0.34850(6) 0.2837(2) 0.23573(6) 0.0163(3) Uani d . . . 1 . .
H H19 0.3593 0.1649 0.2174 0.02 Uiso calc U . R 1 . .
C C20 0.35512(7) 0.2535(2) 0.28783(6) 0.0190(3) Uani d . . . 1 . .
H H20 0.3715 0.1151 0.3052 0.023 Uiso calc U . R 1 . .
C C21 0.33817(6) 0.4227(3) 0.31496(6) 0.0194(3) Uani d . . . 1 . .
H H21 0.3432 0.4015 0.3508 0.023 Uiso calc U . R 1 . .
C C22 0.31371(6) 0.6234(3) 0.28908(6) 0.0196(3) Uani d . . . 1 . .
H H22 0.3006 0.738 0.3069 0.024 Uiso calc U . R 1 . .
C C23 0.30825(6) 0.6583(2) 0.23740(6) 0.0182(3) Uani d . . . 1 . .
H H23 0.2924 0.798 0.2205 0.022 Uiso calc U . R 1 . .
C C24 0.82613(6) 0.3670(2) 0.12100(5) 0.0140(3) Uani d . . . 1 . .
C C25 0.74811(6) 0.5910(2) 0.12345(6) 0.0176(3) Uani d . . . 1 . .
H H25A 0.7513 0.7585 0.1213 0.021 Uiso calc U . R 1 . .
H H25B 0.7169 0.5539 0.138 0.021 Uiso calc U . R 1 . .
C C26 0.73432(6) 0.4780(2) 0.06934(6) 0.0142(3) Uani d . . . 1 . .
H H26 0.726 0.6003 0.0422 0.017 Uiso calc U . R 1 . .
C C27 0.67981(6) 0.3173(2) 0.05368(5) 0.0138(3) Uani d . . . 1 . .
C C28 0.66850(7) 0.1968(2) 0.00203(6) 0.0187(3) Uani d . . . 1 . .
H H28A 0.634 0.0942 -0.0056 0.028 Uiso calc U . R 1 . .
H H28B 0.7042 0.1086 0.0044 0.028 Uiso calc U . R 1 . .
H H28C 0.66 0.3096 -0.0262 0.028 Uiso calc U . R 1 . .
C C29 0.62443(6) 0.4432(2) 0.05379(5) 0.0128(3) Uani d . . . 1 . .
C C30 0.60564(6) 0.6378(2) 0.02279(6) 0.0184(3) Uani d . . . 1 . .
H H30 0.6267 0.6867 0.0012 0.022 Uiso calc U . R 1 . .
C C31 0.55620(7) 0.7600(2) 0.02340(7) 0.0220(3) Uani d . . . 1 . .
H H31 0.544 0.8936 0.0026 0.026 Uiso calc U . R 1 . .
C C32 0.52462(7) 0.6892(3) 0.05397(6) 0.0210(3) Uani d . . . 1 . .
H H32 0.4909 0.7741 0.0544 0.025 Uiso calc U . R 1 . .
C C33 0.54230(6) 0.4941(3) 0.08402(6) 0.0197(3) Uani d . . . 1 . .
H H33 0.5203 0.4438 0.1047 0.024 Uiso calc U . R 1 . .
C C34 0.59210(6) 0.3711(2) 0.08408(6) 0.0168(3) Uani d . . . 1 . .
H H34 0.604 0.2375 0.1049 0.02 Uiso calc U . R 1 . .
C C35 0.88856(6) 0.2788(2) 0.13893(6) 0.0162(3) Uani d . . . 1 . .
C C36 0.90092(7) 0.0717(3) 0.12026(6) 0.0227(3) Uani d . . . 1 . .
H H36 0.8691 -0.0173 0.0969 0.027 Uiso calc U . R 1 . .
C C37 0.96024(8) -0.0044(3) 0.13607(7) 0.0319(4) Uani d . . . 1 . .
H H37 0.9687 -0.146 0.1235 0.038 Uiso calc U . R 1 . .
C C38 1.00684(8) 0.1251(3) 0.16997(7) 0.0346(4) Uani d . . . 1 . .
H H38 1.0472 0.0727 0.1804 0.041 Uiso calc U . R 1 . .
C C39 0.99465(7) 0.3302(3) 0.18851(7) 0.0310(4) Uani d . . . 1 . .
H H39 1.0266 0.4189 0.2117 0.037 Uiso calc U . R 1 . .
C C40 0.93583(7) 0.4073(3) 0.17336(6) 0.0215(3) Uani d . . . 1 . .
H H40 0.9277 0.5482 0.1865 0.026 Uiso calc U . R 1 . .
C C41 0.82050(6) 0.4442(2) 0.20913(5) 0.0134(3) Uani d . . . 1 . .
C C42 0.84645(6) 0.2395(2) 0.23278(6) 0.0151(3) Uani d . . . 1 . .
H H42 0.8552 0.1235 0.2124 0.018 Uiso calc U . R 1 . .
C C43 0.85949(6) 0.2062(2) 0.28613(6) 0.0173(3) Uani d . . . 1 . .
H H43 0.8782 0.0685 0.3022 0.021 Uiso calc U . R 1 . .
C C44 0.84561(6) 0.3712(2) 0.31622(6) 0.0173(3) Uani d . . . 1 . .
H H44 0.8551 0.3481 0.3527 0.021 Uiso calc U . R 1 . .
C C45 0.81770(6) 0.5706(2) 0.29209(6) 0.0174(3) Uani d . . . 1 . .
H H45 0.8069 0.6825 0.3121 0.021 Uiso calc U . R 1 . .
C C46 0.80548(6) 0.6082(2) 0.23913(6) 0.0163(3) Uani d . . . 1 . .
H H46 0.7868 0.7461 0.2232 0.02 Uiso calc U . R 1 . .
F F1 0.21056(4) 0.19130(14) 0.10066(4) 0.0228(2) Uani d . . . 1 . .
F F2 0.69428(4) 0.14717(14) 0.09323(3) 0.02040(19) Uani d . . . 1 . .
N N1 0.30768(5) 0.3817(2) 0.07741(5) 0.0170(2) Uani d . . . 1 . .
N N2 0.31808(5) 0.5304(2) 0.15719(5) 0.0163(2) Uani d . . . 1 . .
N N3 0.79010(5) 0.3575(2) 0.07276(5) 0.0164(2) Uani d . . . 1 . .
N N4 0.80643(5) 0.4886(2) 0.15515(5) 0.0151(2) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.2851(18) ?
C1 N2 . 1.3924(18) ?
C1 C12 . 1.4793(18) ?
C2 N2 . 1.4760(17) ?
C2 C3 . 1.541(2) ?
C3 N1 . 1.4834(17) ?
C3 C4 . 1.5394(19) ?
C4 F1 . 1.4191(15) ?
C4 C5 . 1.512(2) ?
C4 C6 . 1.5147(19) ?
C6 C11 . 1.391(2) ?
C6 C7 . 1.3952(19) ?
C7 C8 . 1.384(2) ?
C8 C9 . 1.383(2) ?
C9 C10 . 1.381(2) ?
C10 C11 . 1.390(2) ?
C12 C17 . 1.394(2) ?
C12 C13 . 1.3947(19) ?
C13 C14 . 1.391(2) ?
C14 C15 . 1.386(2) ?
C15 C16 . 1.387(2) ?
C16 C17 . 1.389(2) ?
C18 C23 . 1.3968(19) ?
C18 C19 . 1.4010(19) ?
C18 N2 . 1.4115(19) ?
C19 C20 . 1.387(2) ?
C20 C21 . 1.387(2) ?
C21 C22 . 1.389(2) ?
C22 C23 . 1.387(2) ?
C24 N3 . 1.2850(18) ?
C24 N4 . 1.3888(17) ?
C24 C35 . 1.4822(18) ?
C25 N4 . 1.4721(17) ?
C25 C26 . 1.544(2) ?
C26 N3 . 1.4811(17) ?
C26 C27 . 1.5364(19) ?
C27 F2 . 1.4191(15) ?
C27 C28 . 1.513(2) ?
C27 C29 . 1.5168(18) ?
C29 C34 . 1.391(2) ?
C29 C30 . 1.3957(18) ?
C30 C31 . 1.388(2) ?
C31 C32 . 1.381(2) ?
C32 C33 . 1.383(2) ?
C33 C34 . 1.3913(19) ?
C35 C36 . 1.392(2) ?
C35 C40 . 1.397(2) ?
C36 C37 . 1.395(2) ?
C37 C38 . 1.386(3) ?
C38 C39 . 1.379(3) ?
C39 C40 . 1.387(2) ?
C41 C46 . 1.3956(19) ?
C41 C42 . 1.3977(18) ?
C41 N4 . 1.4134(18) ?
C42 C43 . 1.390(2) ?
C43 C44 . 1.389(2) ?
C44 C45 . 1.389(2) ?
C45 C46 . 1.387(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 N2 . . 116.60(12) ?
N1 C1 C12 . . 123.22(13) ?
N2 C1 C12 . . 119.90(12) ?
N2 C2 C3 . . 102.12(11) ?
N1 C3 C4 . . 111.42(11) ?
N1 C3 C2 . . 105.70(11) ?
C4 C3 C2 . . 112.86(12) ?
F1 C4 C5 . . 106.98(11) ?
F1 C4 C6 . . 108.07(11) ?
C5 C4 C6 . . 112.35(12) ?
F1 C4 C3 . . 105.97(11) ?
C5 C4 C3 . . 112.62(12) ?
C6 C4 C3 . . 110.48(11) ?
C11 C6 C7 . . 118.99(13) ?
C11 C6 C4 . . 121.92(12) ?
C7 C6 C4 . . 119.09(13) ?
C8 C7 C6 . . 120.31(15) ?
C9 C8 C7 . . 120.38(15) ?
C10 C9 C8 . . 119.72(14) ?
C9 C10 C11 . . 120.28(15) ?
C10 C11 C6 . . 120.28(14) ?
C17 C12 C13 . . 119.55(13) ?
C17 C12 C1 . . 120.09(12) ?
C13 C12 C1 . . 120.36(13) ?
C14 C13 C12 . . 119.78(14) ?
C15 C14 C13 . . 120.40(14) ?
C14 C15 C16 . . 120.04(14) ?
C15 C16 C17 . . 119.85(15) ?
C16 C17 C12 . . 120.38(14) ?
C23 C18 C19 . . 118.79(14) ?
C23 C18 N2 . . 118.39(13) ?
C19 C18 N2 . . 122.79(12) ?
C20 C19 C18 . . 120.12(13) ?
C21 C20 C19 . . 120.88(14) ?
C20 C21 C22 . . 119.09(14) ?
C23 C22 C21 . . 120.62(13) ?
C22 C23 C18 . . 120.44(14) ?
N3 C24 N4 . . 116.67(12) ?
N3 C24 C35 . . 122.51(13) ?
N4 C24 C35 . . 120.41(12) ?
N4 C25 C26 . . 102.20(10) ?
N3 C26 C27 . . 112.04(11) ?
N3 C26 C25 . . 105.97(11) ?
C27 C26 C25 . . 113.06(12) ?
F2 C27 C28 . . 107.02(11) ?
F2 C27 C29 . . 108.05(11) ?
C28 C27 C29 . . 111.94(11) ?
F2 C27 C26 . . 106.02(10) ?
C28 C27 C26 . . 112.92(12) ?
C29 C27 C26 . . 110.53(11) ?
C34 C29 C30 . . 119.11(13) ?
C34 C29 C27 . . 121.95(12) ?
C30 C29 C27 . . 118.95(12) ?
C31 C30 C29 . . 120.09(14) ?
C32 C31 C30 . . 120.60(14) ?
C31 C32 C33 . . 119.62(14) ?
C32 C33 C34 . . 120.33(14) ?
C29 C34 C33 . . 120.24(13) ?
C36 C35 C40 . . 119.46(13) ?
C36 C35 C24 . . 120.51(13) ?
C40 C35 C24 . . 119.99(13) ?
C35 C36 C37 . . 119.65(16) ?
C38 C37 C36 . . 120.44(16) ?
C39 C38 C37 . . 119.96(15) ?
C38 C39 C40 . . 120.22(17) ?
C39 C40 C35 . . 120.27(16) ?
C46 C41 C42 . . 119.17(13) ?
C46 C41 N4 . . 118.28(12) ?
C42 C41 N4 . . 122.49(12) ?
C43 C42 C41 . . 119.84(13) ?
C44 C43 C42 . . 120.94(13) ?
C43 C44 C45 . . 118.98(13) ?
C46 C45 C44 . . 120.70(13) ?
C45 C46 C41 . . 120.28(13) ?
C1 N1 C3 . . 106.86(12) ?
C1 N2 C18 . . 126.38(11) ?
C1 N2 C2 . . 106.73(11) ?
C18 N2 C2 . . 120.10(12) ?
C24 N3 C26 . . 106.95(11) ?
C24 N4 C41 . . 126.81(11) ?
C24 N4 C25 . . 107.17(11) ?
C41 N4 C25 . . 120.07(11) ?

