# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1845204'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2'
_chemical_formula_weight         250.33

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9134(5)
_cell_length_b                   7.7193(7)
_cell_length_c                   31.935(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1457.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6233
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4

_diffrn_reflns_number            9798
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2553
_reflns_number_gt                2292
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.997

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 III'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.1467P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 847 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2553
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0714
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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_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 0.5652(3) 0.3010(2) 0.62123(4) 0.0342(4) Uani 1 1 d . . . . .
N2 N 0.4222(4) -0.0353(3) 0.68036(6) 0.0723(7) Uani 1 1 d . . . . .
C1 C 0.6929(3) 0.2100(3) 0.65375(5) 0.0356(5) Uani 1 1 d . . . . .
H1 H 0.8282 0.1547 0.6406 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5419(4) 0.0722(3) 0.66944(6) 0.0472(5) Uani 1 1 d . . . . .
C3 C 0.6523(3) 0.3075(2) 0.58507(5) 0.0273(4) Uani 1 1 d . . . . .
H3 H 0.7951 0.2546 0.5804 0.033 Uiso 1 1 calc R U . . .
C4 C 0.5382(3) 0.3947(2) 0.55010(5) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.6406(3) 0.4032(2) 0.51156(5) 0.0239(4) Uani 1 1 d . . . . .
H5 H 0.7840 0.3502 0.5076 0.029 Uiso 1 1 calc R U . . .
C6 C 0.5359(3) 0.4897(2) 0.47752(5) 0.0227(4) Uani 1 1 d . . . . .
C7 C 0.6410(3) 0.5054(2) 0.43775(5) 0.0286(4) Uani 1 1 d . . . . .
H7 H 0.7848 0.4540 0.4331 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5373(3) 0.5936(2) 0.40602(5) 0.0341(5) Uani 1 1 d . . . . .
H8 H 0.6108 0.6055 0.3797 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3222(3) 0.6669(2) 0.41216(6) 0.0338(5) Uani 1 1 d . . . . .
H9 H 0.2501 0.7263 0.3898 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2163(3) 0.6534(2) 0.44990(5) 0.0293(4) Uani 1 1 d . . . . .
H10 H 0.0710 0.7036 0.4536 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3200(3) 0.5655(2) 0.48373(5) 0.0234(4) Uani 1 1 d . . . . .
C12 C 0.2166(3) 0.5530(2) 0.52378(5) 0.0263(4) Uani 1 1 d . . . . .
H12 H 0.0715 0.6026 0.5281 0.032 Uiso 1 1 calc R U . . .
C13 C 0.3224(3) 0.4712(2) 0.55587(5) 0.0260(4) Uani 1 1 d . . . . .
H13 H 0.2511 0.4651 0.5825 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7741(3) 0.3326(3) 0.68914(5) 0.0381(5) Uani 1 1 d . . . . .
C15 C 0.5771(4) 0.4346(4) 0.70726(7) 0.0601(7) Uani 1 1 d . . . . .
H15A H 0.4660 0.3542 0.7191 0.090 Uiso 1 1 calc R U . . .
H15B H 0.6325 0.5122 0.7293 0.090 Uiso 1 1 calc R U . . .
H15C H 0.5059 0.5030 0.6850 0.090 Uiso 1 1 calc R U . . .
C16 C 0.8856(4) 0.2227(3) 0.72342(6) 0.0510(6) Uani 1 1 d . . . . .
H16A H 1.0122 0.1576 0.7114 0.077 Uiso 1 1 calc R U . . .
H16B H 0.9415 0.2987 0.7457 0.077 Uiso 1 1 calc R U . . .
H16C H 0.7743 0.1418 0.7350 0.077 Uiso 1 1 calc R U . . .
C17 C 0.9495(4) 0.4547(3) 0.67044(6) 0.0514(6) Uani 1 1 d . . . . .
H17A H 1.0751 0.3870 0.6589 0.077 Uiso 1 1 calc R U . . .
H17B H 0.8798 0.5232 0.6481 0.077 Uiso 1 1 calc R U . . .
H17C H 1.0065 0.5323 0.6923 0.077 Uiso 1 1 calc R U . . .


_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 C3 1.266(2) . ?
N1 C1 1.464(2) . ?
N2 C2 1.145(3) . ?
C1 C2 1.476(3) . ?
C1 C14 1.550(3) . ?
C1 H1 1.0000 . ?
C3 C4 1.468(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(2) . ?
C4 C13 1.419(2) . ?
C5 C6 1.418(2) . ?
C5 H5 0.9500 . ?
C6 C11 1.418(2) . ?
C6 C7 1.419(2) . ?
C7 C8 1.366(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.362(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.415(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.421(2) . ?
C12 C13 1.357(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.520(3) . ?
C14 C17 1.524(3) . ?
C14 C16 1.533(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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
C3 N1 C1 117.18(15) . . ?
N1 C1 C2 105.94(15) . . ?
N1 C1 C14 112.57(15) . . ?
C2 C1 C14 112.31(15) . . ?
N1 C1 H1 108.6 . . ?
C2 C1 H1 108.6 . . ?
C14 C1 H1 108.6 . . ?
N2 C2 C1 177.9(2) . . ?
N1 C3 C4 121.72(16) . . ?
N1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C13 119.56(15) . . ?
C5 C4 C3 120.09(15) . . ?
C13 C4 C3 120.35(14) . . ?
C4 C5 C6 121.12(15) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C11 C6 C5 118.71(14) . . ?
C11 C6 C7 118.96(15) . . ?
C5 C6 C7 122.32(15) . . ?
C8 C7 C6 120.64(17) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.20(17) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C10 C9 C8 120.57(17) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.88(16) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 118.73(15) . . ?
C10 C11 C12 122.25(15) . . ?
C6 C11 C12 119.01(14) . . ?
C13 C12 C11 120.89(15) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C4 120.70(15) . . ?
C12 C13 H13 119.7 . . ?
C4 C13 H13 119.7 . . ?
C15 C14 C17 110.51(19) . . ?
C15 C14 C16 110.13(17) . . ?
C17 C14 C16 109.21(17) . . ?
C15 C14 C1 110.87(16) . . ?
C17 C14 C1 107.62(15) . . ?
C16 C14 C1 108.43(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
C3 N1 C1 C2 -122.44(18) . . . . ?
C3 N1 C1 C14 114.45(19) . . . . ?
C1 N1 C3 C4 179.65(15) . . . . ?
N1 C3 C4 C5 178.23(17) . . . . ?
N1 C3 C4 C13 -1.5(3) . . . . ?
C13 C4 C5 C6 1.1(2) . . . . ?
C3 C4 C5 C6 -178.69(15) . . . . ?
C4 C5 C6 C11 -1.1(2) . . . . ?
C4 C5 C6 C7 177.91(16) . . . . ?
C11 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C8 -178.30(16) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C6 -0.7(2) . . . . ?
C9 C10 C11 C12 178.35(16) . . . . ?
C5 C6 C11 C10 179.40(16) . . . . ?
C7 C6 C11 C10 0.4(2) . . . . ?
C5 C6 C11 C12 0.3(2) . . . . ?
C7 C6 C11 C12 -178.73(16) . . . . ?
C10 C11 C12 C13 -178.54(16) . . . . ?
C6 C11 C12 C13 0.5(2) . . . . ?
C11 C12 C13 C4 -0.6(3) . . . . ?
C5 C4 C13 C12 -0.2(2) . . . . ?
C3 C4 C13 C12 179.53(16) . . . . ?
N1 C1 C14 C15 53.7(2) . . . . ?
C2 C1 C14 C15 -65.8(2) . . . . ?
N1 C1 C14 C17 -67.25(19) . . . . ?
C2 C1 C14 C17 173.27(17) . . . . ?
N1 C1 C14 C16 174.73(16) . . . . ?
C2 C1 C14 C16 55.3(2) . . . . ?

_refine_diff_density_max         0.140
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.026

####################################################################### 
# 
# 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_7b
_database_code_depnum_ccdc_archive 'CCDC 1845205'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.9479(5)
_cell_length_b                   12.3654(11)
_cell_length_c                   21.1408(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1554.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            25831
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2729
_reflns_number_gt                2476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.698
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 III'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+0.1630P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2729
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0730
_refine_ls_wR_factor_gt          0.0708
_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_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
O1 O 0.5683(2) 0.31185(11) 0.41266(6) 0.0375(4) Uani 1 1 d . . . . .
N1 N 0.2894(3) 0.84951(12) 0.66937(7) 0.0295(4) Uani 1 1 d . . . . .
N2 N 0.4483(3) 1.09859(15) 0.70948(9) 0.0467(5) Uani 1 1 d . . . . .
C1 C 0.1655(3) 0.93687(14) 0.70051(9) 0.0282(4) Uani 1 1 d . . . . .
H1 H 0.0361 0.9586 0.6731 0.034 Uiso 1 1 calc R U . . .
C2 C 0.3228(3) 1.02868(16) 0.70573(9) 0.0325(4) Uani 1 1 d . . . . .
C3 C 0.1974(3) 0.80478(15) 0.62211(8) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.0556 0.8305 0.6079 0.034 Uiso 1 1 calc R U . . .
C4 C 0.3043(3) 0.71428(15) 0.58872(8) 0.0275(4) Uani 1 1 d . . . . .
C5 C 0.2013(3) 0.66892(15) 0.53676(8) 0.0279(4) Uani 1 1 d . . . . .
H5 H 0.0619 0.6974 0.5225 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2987(3) 0.58087(14) 0.50417(8) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.1962(3) 0.53102(15) 0.45074(8) 0.0299(4) Uani 1 1 d . . . . .
H7 H 0.0581 0.5588 0.4351 0.036 Uiso 1 1 calc R U . . .
C8 C 0.2921(3) 0.44453(15) 0.42165(8) 0.0302(4) Uani 1 1 d . . . . .
H8 H 0.2212 0.4128 0.3859 0.036 Uiso 1 1 calc R U . . .
C9 C 0.4968(3) 0.40165(15) 0.44431(8) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.6051(3) 0.44884(15) 0.49445(8) 0.0279(4) Uani 1 1 d . . . . .
H10 H 0.7453 0.4210 0.5084 0.033 Uiso 1 1 calc R U . . .
C11 C 0.5085(3) 0.53893(14) 0.52539(8) 0.0251(4) Uani 1 1 d . . . . .
C12 C 0.6127(3) 0.58860(15) 0.57817(8) 0.0296(4) Uani 1 1 d . . . . .
H12 H 0.7546 0.5628 0.5922 0.035 Uiso 1 1 calc R U . . .
C13 C 0.5138(3) 0.67264(15) 0.60921(8) 0.0303(4) Uani 1 1 d . . . . .
H13 H 0.5861 0.7036 0.6449 0.036 Uiso 1 1 calc R U . . .
C14 C 0.0746(3) 0.90232(14) 0.76635(8) 0.0275(4) Uani 1 1 d . . . . .
C15 C -0.0955(4) 0.81147(17) 0.75619(10) 0.0432(5) Uani 1 1 d . . . . .
H15A H -0.2178 0.8374 0.7291 0.065 Uiso 1 1 calc R U . . .
H15B H -0.0210 0.7499 0.7359 0.065 Uiso 1 1 calc R U . . .
H15C H -0.1569 0.7888 0.7971 0.065 Uiso 1 1 calc R U . . .
C16 C -0.0438(3) 0.99961(15) 0.79629(9) 0.0339(5) Uani 1 1 d . . . . .
H16A H -0.1661 1.0237 0.7686 0.051 Uiso 1 1 calc R U . . .
H16B H -0.1053 0.9788 0.8375 0.051 Uiso 1 1 calc R U . . .
H16C H 0.0644 1.0586 0.8019 0.051 Uiso 1 1 calc R U . . .
C17 C 0.2661(3) 0.86316(16) 0.80852(9) 0.0350(5) Uani 1 1 d . . . . .
H17A H 0.3743 0.9220 0.8148 0.053 Uiso 1 1 calc R U . . .
H17B H 0.2056 0.8406 0.8496 0.053 Uiso 1 1 calc R U . . .
H17C H 0.3416 0.8017 0.7883 0.053 Uiso 1 1 calc R U . . .
C91 C 0.7647(4) 0.25916(17) 0.43543(10) 0.0421(5) Uani 1 1 d . . . . .
H91A H 0.7444 0.2405 0.4801 0.063 Uiso 1 1 calc R U . . .
H91B H 0.8942 0.3076 0.4310 0.063 Uiso 1 1 calc R U . . .
H91C H 0.7909 0.1931 0.4109 0.063 Uiso 1 1 calc R U . . .


_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
O1 C9 1.364(2) . ?
O1 C91 1.421(2) . ?
N1 C3 1.266(2) . ?
N1 C1 1.464(2) . ?
N2 C2 1.145(2) . ?
C1 C2 1.475(3) . ?
C1 C14 1.553(2) . ?
C1 H1 1.0000 . ?
C3 C4 1.468(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 C13 1.416(3) . ?
C5 C6 1.413(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.424(3) . ?
C6 C11 1.424(2) . ?
C7 C8 1.359(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.371(2) . ?
C10 C11 1.414(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.417(2) . ?
C12 C13 1.363(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C17 1.526(3) . ?
C14 C15 1.527(3) . ?
C14 C16 1.531(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?

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
C9 O1 C91 117.59(14) . . ?
C3 N1 C1 117.36(16) . . ?
N1 C1 C2 106.39(14) . . ?
N1 C1 C14 112.04(14) . . ?
C2 C1 C14 111.44(15) . . ?
N1 C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
C14 C1 H1 109.0 . . ?
N2 C2 C1 178.7(2) . . ?
N1 C3 C4 121.70(17) . . ?
N1 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C13 119.16(17) . . ?
C5 C4 C3 120.11(16) . . ?
C13 C4 C3 120.74(16) . . ?
C4 C5 C6 121.38(17) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C7 123.04(17) . . ?
C5 C6 C11 119.10(16) . . ?
C7 C6 C11 117.86(16) . . ?
C8 C7 C6 121.34(17) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C9 120.26(17) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
O1 C9 C10 125.40(17) . . ?
O1 C9 C8 114.08(16) . . ?
C10 C9 C8 120.52(17) . . ?
C9 C10 C11 120.15(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 121.89(16) . . ?
C10 C11 C6 119.82(16) . . ?
C12 C11 C6 118.28(16) . . ?
C13 C12 C11 121.40(17) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C4 120.66(17) . . ?
C12 C13 H13 119.7 . . ?
C4 C13 H13 119.7 . . ?
C17 C14 C15 110.10(16) . . ?
C17 C14 C16 110.56(15) . . ?
C15 C14 C16 109.38(15) . . ?
C17 C14 C1 110.54(14) . . ?
C15 C14 C1 107.87(15) . . ?
C16 C14 C1 108.33(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O1 C91 H91A 109.5 . . ?
O1 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
O1 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?

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
C3 N1 C1 C2 -129.28(17) . . . . ?
C3 N1 C1 C14 108.71(18) . . . . ?
C1 N1 C3 C4 -178.11(15) . . . . ?
N1 C3 C4 C5 -178.78(17) . . . . ?
N1 C3 C4 C13 1.1(3) . . . . ?
C13 C4 C5 C6 1.0(3) . . . . ?
C3 C4 C5 C6 -179.18(16) . . . . ?
C4 C5 C6 C7 179.27(16) . . . . ?
C4 C5 C6 C11 -0.5(3) . . . . ?
C5 C6 C7 C8 -178.19(17) . . . . ?
C11 C6 C7 C8 1.5(3) . . . . ?
C6 C7 C8 C9 0.3(3) . . . . ?
C91 O1 C9 C10 3.6(3) . . . . ?
C91 O1 C9 C8 -175.61(16) . . . . ?
C7 C8 C9 O1 176.96(16) . . . . ?
C7 C8 C9 C10 -2.3(3) . . . . ?
O1 C9 C10 C11 -176.93(16) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C9 C10 C11 C12 178.67(16) . . . . ?
C9 C10 C11 C6 -0.3(3) . . . . ?
C5 C6 C11 C10 178.16(16) . . . . ?
C7 C6 C11 C10 -1.6(2) . . . . ?
C5 C6 C11 C12 -0.8(2) . . . . ?
C7 C6 C11 C12 179.45(16) . . . . ?
C10 C11 C12 C13 -177.33(17) . . . . ?
C6 C11 C12 C13 1.6(3) . . . . ?
C11 C12 C13 C4 -1.1(3) . . . . ?
C5 C4 C13 C12 -0.2(3) . . . . ?
C3 C4 C13 C12 179.98(17) . . . . ?
N1 C1 C14 C17 56.5(2) . . . . ?
C2 C1 C14 C17 -62.58(19) . . . . ?
N1 C1 C14 C15 -63.92(19) . . . . ?
C2 C1 C14 C15 177.00(15) . . . . ?
N1 C1 C14 C16 177.78(15) . . . . ?
C2 C1 C14 C16 58.70(18) . . . . ?

_refine_diff_density_max         0.160
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.031

####################################################################### 
# 
# 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_8a
_database_code_depnum_ccdc_archive 'CCDC 1845206'
_audit_update_record             
;
2018-05-24 deposited with the CCDC.
2018-08-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 F N2'
_chemical_formula_weight         296.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.4325(3)
_cell_length_b                   15.1525(7)
_cell_length_c                   15.7404(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1534.19(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.3

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.084
_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  0.967
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'Bruker SADABS-2014/5)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec Microfocus'
_diffrn_radiation_monochromator  'multi layered optics'
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4

_diffrn_reflns_number            20442
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.588
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2711
_reflns_number_gt                2544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _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 III'
_computing_cell_refinement       'Bruker SAINT-V 8.34A'
_computing_data_reduction        'Bruker SAINT-V 8.34A'
_computing_structure_solution    'SHELXTL-XT-2014/4 (Bruker AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.2403P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1020 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2711
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0699
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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_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
F1 F 0.4265(2) 0.80369(9) 0.96700(7) 0.0461(4) Uani 1 1 d . . . . .
N1 N 0.6900(3) 0.58410(10) 0.63944(10) 0.0263(4) Uani 1 1 d . . . . .
C1 C 0.6899(3) 0.52019(13) 0.56956(12) 0.0269(4) Uani 1 1 d . . . . .
H1 H 0.5719 0.4781 0.5779 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8883(4) 0.47076(15) 0.57561(13) 0.0368(5) Uani 1 1 d . . . . .
C3 C 0.5292(3) 0.58409(12) 0.68648(12) 0.0242(4) Uani 1 1 d . . . . .
H3 H 0.4200 0.5440 0.6737 0.029 Uiso 1 1 calc R U . . .
C4 C 0.5048(3) 0.64313(12) 0.75960(11) 0.0229(4) Uani 1 1 d . . . . .
C5 C 0.3201(3) 0.64230(13) 0.80523(13) 0.0288(4) Uani 1 1 d . . . . .
H5 H 0.2109 0.6040 0.7880 0.035 Uiso 1 1 calc R U . . .
C6 C 0.2921(3) 0.69609(14) 0.87520(13) 0.0338(5) Uani 1 1 d . . . . .
H6 H 0.1657 0.6954 0.9064 0.041 Uiso 1 1 calc R U . . .
C7 C 0.4525(3) 0.75040(13) 0.89809(12) 0.0304(5) Uani 1 1 d . . . . .
C8 C 0.6382(3) 0.75426(14) 0.85518(12) 0.0309(5) Uani 1 1 d . . . . .
H8 H 0.7457 0.7931 0.8730 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6640(3) 0.69989(13) 0.78517(12) 0.0282(5) Uani 1 1 d . . . . .
H9 H 0.7909 0.7012 0.7543 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6675(3) 0.56471(12) 0.48114(11) 0.0210(4) Uani 1 1 d . . . . .
C11 C 0.8543(3) 0.62339(12) 0.45924(11) 0.0226(4) Uani 1 1 d . . . . .
H11A H 0.8696 0.6701 0.5027 0.027 Uiso 1 1 calc R U . . .
H11B H 0.9829 0.5875 0.4590 0.027 Uiso 1 1 calc R U . . .
C12 C 0.8227(3) 0.66558(12) 0.37162(12) 0.0233(4) Uani 1 1 d . . . . .
H12 H 0.9450 0.7037 0.3577 0.028 Uiso 1 1 calc R U . . .
C13 C 0.8011(3) 0.59330(13) 0.30424(12) 0.0264(4) Uani 1 1 d . . . . .
H13A H 0.9291 0.5570 0.3028 0.032 Uiso 1 1 calc R U . . .
H13B H 0.7820 0.6204 0.2476 0.032 Uiso 1 1 calc R U . . .
C14 C 0.6135(3) 0.53476(13) 0.32543(12) 0.0249(4) Uani 1 1 d . . . . .
H14 H 0.5994 0.4875 0.2815 0.030 Uiso 1 1 calc R U . . .
C15 C 0.6453(3) 0.49259(12) 0.41289(11) 0.0245(4) Uani 1 1 d . . . . .
H15A H 0.7719 0.4554 0.4121 0.029 Uiso 1 1 calc R U . . .
H15B H 0.5251 0.4543 0.4266 0.029 Uiso 1 1 calc R U . . .
C16 C 0.4698(3) 0.62169(12) 0.48140(12) 0.0220(4) Uani 1 1 d . . . . .
H16A H 0.3481 0.5846 0.4958 0.026 Uiso 1 1 calc R U . . .
H16B H 0.4824 0.6684 0.5250 0.026 Uiso 1 1 calc R U . . .
C17 C 0.4377(3) 0.66385(13) 0.39394(12) 0.0239(4) Uani 1 1 d . . . . .
H17 H 0.3089 0.7008 0.3947 0.029 Uiso 1 1 calc R U . . .
C18 C 0.6253(3) 0.72202(12) 0.37259(12) 0.0257(4) Uani 1 1 d . . . . .
H18A H 0.6050 0.7499 0.3163 0.031 Uiso 1 1 calc R U . . .
H18B H 0.6390 0.7694 0.4155 0.031 Uiso 1 1 calc R U . . .
C19 C 0.4160(3) 0.59139(13) 0.32678(12) 0.0270(4) Uani 1 1 d . . . . .
H19A H 0.3938 0.6184 0.2702 0.032 Uiso 1 1 calc R U . . .
H19B H 0.2942 0.5539 0.3401 0.032 Uiso 1 1 calc R U . . .
N2 N 1.0431(4) 0.43417(16) 0.58100(14) 0.0588(6) Uani 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 1.363(2) . ?
N1 C3 1.272(2) . ?
N1 C1 1.465(2) . ?
C1 C2 1.482(3) . ?
C1 C10 1.553(2) . ?
C1 H1 1.0000 . ?
C2 N2 1.143(3) . ?
C3 C4 1.466(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(3) . ?
C4 C9 1.397(3) . ?
C5 C6 1.382(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.368(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(3) . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.534(2) . ?
C10 C16 1.537(3) . ?
C10 C15 1.539(2) . ?
C11 C12 1.534(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.531(3) . ?
C12 C18 1.531(3) . ?
C12 H12 1.0000 . ?
C13 C14 1.534(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.531(3) . ?
C14 C19 1.533(3) . ?
C14 H14 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.532(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.531(3) . ?
C17 C18 1.531(3) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
C3 N1 C1 115.89(17) . . ?
N1 C1 C2 106.58(16) . . ?
N1 C1 C10 112.67(15) . . ?
C2 C1 C10 110.92(16) . . ?
N1 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
C10 C1 H1 108.9 . . ?
N2 C2 C1 178.6(3) . . ?
N1 C3 C4 122.95(17) . . ?
N1 C3 H3 118.5 . . ?
C4 C3 H3 118.5 . . ?
C5 C4 C9 118.95(17) . . ?
C5 C4 C3 119.48(17) . . ?
C9 C4 C3 121.57(17) . . ?
C6 C5 C4 121.20(19) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 117.82(19) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
F1 C7 C6 118.26(18) . . ?
F1 C7 C8 118.24(18) . . ?
C6 C7 C8 123.50(18) . . ?
C7 C8 C9 118.03(18) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 H8 121.0 . . ?
C8 C9 C4 120.49(19) . . ?
C8 C9 H9 119.8 . . ?
C4 C9 H9 119.8 . . ?
C11 C10 C16 108.85(14) . . ?
C11 C10 C15 109.10(14) . . ?
C16 C10 C15 108.91(15) . . ?
C11 C10 C1 112.34(15) . . ?
C16 C10 C1 108.58(15) . . ?
C15 C10 C1 109.00(14) . . ?
C12 C11 C10 109.87(14) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C18 109.35(15) . . ?
C13 C12 C11 109.68(15) . . ?
C18 C12 C11 109.50(15) . . ?
C13 C12 H12 109.4 . . ?
C18 C12 H12 109.4 . . ?
C11 C12 H12 109.4 . . ?
C12 C13 C14 109.53(15) . . ?
C12 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C19 109.36(16) . . ?
C15 C14 C13 109.37(16) . . ?
C19 C14 C13 109.35(15) . . ?
C15 C14 H14 109.6 . . ?
C19 C14 H14 109.6 . . ?
C13 C14 H14 109.6 . . ?
C14 C15 C10 110.09(15) . . ?
C14 C15 H15A 109.6 . . ?
C10 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C10 C15 H15B 109.6 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C10 110.08(15) . . ?
C17 C16 H16A 109.6 . . ?
C10 C16 H16A 109.6 . . ?
C17 C16 H16B 109.6 . . ?
C10 C16 H16B 109.6 . . ?
H16A C16 H16B 108.2 . . ?
C19 C17 C18 109.47(16) . . ?
C19 C17 C16 109.51(15) . . ?
C18 C17 C16 109.35(15) . . ?
C19 C17 H17 109.5 . . ?
C18 C17 H17 109.5 . . ?
C16 C17 H17 109.5 . . ?
C12 C18 C17 109.51(14) . . ?
C12 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
C12 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
C17 C19 C14 109.60(15) . . ?
C17 C19 H19A 109.8 . . ?
C14 C19 H19A 109.8 . . ?
C17 C19 H19B 109.8 . . ?
C14 C19 H19B 109.8 . . ?
H19A C19 H19B 108.2 . . ?

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
C3 N1 C1 C2 -128.58(18) . . . . ?
C3 N1 C1 C10 109.54(18) . . . . ?
C1 N1 C3 C4 179.38(16) . . . . ?
N1 C3 C4 C5 176.69(18) . . . . ?
N1 C3 C4 C9 -3.9(3) . . . . ?
C9 C4 C5 C6 -0.3(3) . . . . ?
C3 C4 C5 C6 179.13(18) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 F1 -179.99(17) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
F1 C7 C8 C9 179.95(17) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
C3 C4 C9 C8 -179.16(17) . . . . ?
N1 C1 C10 C11 65.0(2) . . . . ?
C2 C1 C10 C11 -54.4(2) . . . . ?
N1 C1 C10 C16 -55.5(2) . . . . ?
C2 C1 C10 C16 -174.86(16) . . . . ?
N1 C1 C10 C15 -173.99(16) . . . . ?
C2 C1 C10 C15 66.6(2) . . . . ?
C16 C10 C11 C12 -59.54(18) . . . . ?
C15 C10 C11 C12 59.19(18) . . . . ?
C1 C10 C11 C12 -179.82(14) . . . . ?
C10 C11 C12 C13 -59.88(19) . . . . ?
C10 C11 C12 C18 60.11(18) . . . . ?
C18 C12 C13 C14 -60.2(2) . . . . ?
C11 C12 C13 C14 59.9(2) . . . . ?
C12 C13 C14 C15 -59.8(2) . . . . ?
C12 C13 C14 C19 59.9(2) . . . . ?
C19 C14 C15 C10 -59.91(19) . . . . ?
C13 C14 C15 C10 59.8(2) . . . . ?
C11 C10 C15 C14 -59.40(19) . . . . ?
C16 C10 C15 C14 59.29(19) . . . . ?
C1 C10 C15 C14 177.60(16) . . . . ?
C11 C10 C16 C17 59.65(19) . . . . ?
C15 C10 C16 C17 -59.19(18) . . . . ?
C1 C10 C16 C17 -177.77(15) . . . . ?
C10 C16 C17 C19 59.90(19) . . . . ?
C10 C16 C17 C18 -60.04(18) . . . . ?
C13 C12 C18 C17 60.2(2) . . . . ?
C11 C12 C18 C17 -59.99(19) . . . . ?
C19 C17 C18 C12 -60.09(19) . . . . ?
C16 C17 C18 C12 59.87(19) . . . . ?
C18 C17 C19 C14 59.90(19) . . . . ?
C16 C17 C19 C14 -60.0(2) . . . . ?
C15 C14 C19 C17 60.0(2) . . . . ?
C13 C14 C19 C17 -59.8(2) . . . . ?

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032

