# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_RaoY-2
_database_code_depnum_ccdc_archive 'CCDC 1524150'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        41b
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H19 F N2 O'
_chemical_formula_sum            'C25 H19 F N2 O'
_chemical_formula_weight         382.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   7.2657(2)
_cell_length_b                   15.2058(5)
_cell_length_c                   19.3128(8)
_cell_angle_alpha                110.971(3)
_cell_angle_beta                 99.332(3)
_cell_angle_gamma                95.705(2)
_cell_volume                     1937.08(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173.0(1)
_cell_measurement_reflns_used    9484
_cell_measurement_theta_min      4.6
_cell_measurement_theta_max      76.8

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.704
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_reflns_number            17921
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.726
_diffrn_reflns_theta_max         76.924
_diffrn_reflns_theta_full        74.500
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8027
_reflns_number_gt                7104
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0010P)²+3.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8027
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 1.0163(3) 0.86393(12) 0.73545(9) 0.0504(5) Uani 1 1 d . . . . .
F2 F 0.2321(3) 0.13801(13) -0.21801(10) 0.0555(5) Uani 1 1 d . . . . .
O1 O 0.3112(2) 0.62529(13) 0.33973(10) 0.0332(4) Uani 1 1 d . . . . .
O2 O -0.0474(3) 0.28119(15) 0.17231(11) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.5247(3) 0.86894(15) 0.59157(13) 0.0336(5) Uani 1 1 d . . . . .
N2 N 0.4724(3) 0.73466(14) 0.45386(12) 0.0270(4) Uani 1 1 d . . . . .
H2 H 0.554(4) 0.743(2) 0.4963(18) 0.032 Uiso 1 1 d . U . . .
N3 N -0.1005(3) 0.28172(15) -0.08086(12) 0.0311(5) Uani 1 1 d . . . . .
N4 N -0.0072(3) 0.27658(15) 0.05707(12) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.037(4) 0.246(2) 0.0185(17) 0.032 Uiso 1 1 d . U . . .
C1 C 0.4371(3) 0.64740(16) 0.39640(13) 0.0240(5) Uani 1 1 d . . . . .
C2 C 0.5550(3) 0.57489(15) 0.40828(13) 0.0235(5) Uani 1 1 d . . . . .
H2A H 0.5261 0.5191 0.3612 0.028 Uiso 1 1 calc R U . . .
H2B H 0.5111 0.5551 0.4461 0.028 Uiso 1 1 calc R U . . .
C3 C 0.7724(3) 0.60271(15) 0.43274(13) 0.0210(4) Uani 1 1 d . . . . .
C4 C 0.8391(3) 0.67431(16) 0.51354(13) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.9373(3) 0.76535(17) 0.53081(14) 0.0278(5) Uani 1 1 d . . . . .
H5 H 0.9627 0.7837 0.4918 0.033 Uiso 1 1 calc R U . . .
C6 C 0.9981(4) 0.82944(18) 0.60577(15) 0.0330(6) Uani 1 1 d . . . . .
H6 H 1.0635 0.8904 0.6173 0.040 Uiso 1 1 calc R U . . .
C7 C 0.9591(4) 0.80053(18) 0.66233(14) 0.0327(6) Uani 1 1 d . . . . .
C8 C 0.8644(4) 0.71159(18) 0.64870(14) 0.0307(5) Uani 1 1 d . . . . .
H8 H 0.8415 0.6938 0.6883 0.037 Uiso 1 1 calc R U . . .
C9 C 0.8034(3) 0.64870(16) 0.57331(13) 0.0250(5) Uani 1 1 d . . . . .
H9 H 0.7372 0.5881 0.5625 0.030 Uiso 1 1 calc R U . . .
C10 C 0.8692(3) 0.62022(17) 0.37091(13) 0.0257(5) Uani 1 1 d . . . . .
H10 H 0.9978 0.6557 0.3952 0.031 Uiso 1 1 calc R U . . .
C11 C 0.8787(4) 0.51226(17) 0.33596(14) 0.0288(5) Uani 1 1 d . . . . .
H11A H 0.9981 0.4988 0.3218 0.035 Uiso 1 1 calc R U . . .
H11B H 0.7723 0.4750 0.2949 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8617(3) 0.50798(16) 0.41375(13) 0.0244(5) Uani 1 1 d . . . . .
H12 H 0.9883 0.5220 0.4460 0.029 Uiso 1 1 calc R U . . .
C13 C 0.7776(4) 0.66560(18) 0.32305(14) 0.0315(5) Uani 1 1 d . . . . .
C14 C 0.7051(5) 0.7016(2) 0.28366(17) 0.0456(7) Uani 1 1 d . . . . .
H14 H 0.646(5) 0.734(2) 0.258(2) 0.055 Uiso 1 1 d . U . . .
C15 C 0.7562(3) 0.42163(17) 0.41411(14) 0.0272(5) Uani 1 1 d . . . . .
C16 C 0.6701(4) 0.34981(18) 0.41152(16) 0.0333(6) Uani 1 1 d . . . . .
H16 H 0.608(4) 0.292(2) 0.4095(18) 0.040 Uiso 1 1 d . U . . .
C17 C 0.3778(3) 0.81227(16) 0.45977(14) 0.0267(5) Uani 1 1 d . . . . .
C18 C 0.2611(4) 0.82328(19) 0.40132(16) 0.0330(6) Uani 1 1 d . . . . .
H18 H 0.2339 0.7754 0.3530 0.040 Uiso 1 1 calc R U . . .
C19 C 0.1822(4) 0.9075(2) 0.41465(19) 0.0405(7) Uani 1 1 d . . . . .
H19 H 0.1035 0.9143 0.3745 0.049 Uiso 1 1 calc R U . . .
C20 C 0.2176(4) 0.97878(19) 0.4842(2) 0.0425(7) Uani 1 1 d . . . . .
H20 H 0.1660 1.0341 0.4911 0.051 Uiso 1 1 calc R U . . .
C21 C 0.3335(4) 0.96884(18) 0.54651(18) 0.0358(6) Uani 1 1 d . . . . .
C22 C 0.3744(4) 1.03807(19) 0.6216(2) 0.0467(8) Uani 1 1 d . . . . .
H22 H 0.3261 1.0948 0.6322 0.056 Uiso 1 1 calc R U . . .
C23 C 0.4844(5) 1.0215(2) 0.67808(19) 0.0485(8) Uani 1 1 d . . . . .
H23 H 0.5106 1.0663 0.7277 0.058 Uiso 1 1 calc R U . . .
C24 C 0.5580(5) 0.9362(2) 0.66085(17) 0.0429(7) Uani 1 1 d . . . . .
H24 H 0.6341 0.9262 0.7000 0.051 Uiso 1 1 calc R U . . .
C25 C 0.4138(4) 0.88510(17) 0.53473(15) 0.0293(5) Uani 1 1 d . . . . .
C26 C 0.0222(3) 0.24841(17) 0.11711(14) 0.0270(5) Uani 1 1 d . . . . .
C27 C 0.1394(3) 0.16968(17) 0.10997(14) 0.0270(5) Uani 1 1 d . . . . .
H27A H 0.0632 0.1108 0.0724 0.032 Uiso 1 1 calc R U . . .
H27B H 0.1606 0.1617 0.1581 0.032 Uiso 1 1 calc R U . . .
C28 C 0.3334(3) 0.18025(16) 0.08829(14) 0.0255(5) Uani 1 1 d . . . . .
C29 C 0.3163(3) 0.16981(16) 0.00648(14) 0.0263(5) Uani 1 1 d . . . . .
C30 C 0.3896(4) 0.24292(18) -0.01401(15) 0.0315(5) Uani 1 1 d . . . . .
H30 H 0.4564 0.2999 0.0236 0.038 Uiso 1 1 calc R U . . .
C31 C 0.3649(4) 0.23230(19) -0.08939(16) 0.0368(6) Uani 1 1 d . . . . .
H31 H 0.4149 0.2810 -0.1029 0.044 Uiso 1 1 calc R U . . .
C32 C 0.2645(4) 0.1478(2) -0.14340(15) 0.0366(6) Uani 1 1 d . . . . .
C33 C 0.1929(4) 0.07291(19) -0.12679(16) 0.0407(6) Uani 1 1 d . . . . .
H33 H 0.1282 0.0159 -0.1650 0.049 Uiso 1 1 calc R U . . .
C34 C 0.2201(4) 0.08490(18) -0.05085(16) 0.0351(6) Uani 1 1 d . . . . .
H34 H 0.1729 0.0349 -0.0381 0.042 Uiso 1 1 calc R U . . .
C35 C 0.4807(3) 0.26542(17) 0.15033(15) 0.0299(5) Uani 1 1 d . . . . .
H35 H 0.5861 0.2794 0.1279 0.036 Uiso 1 1 calc R U . . .
C36 C 0.5342(4) 0.1976(2) 0.19127(17) 0.0382(6) Uani 1 1 d . . . . .
H36A H 0.4630 0.1982 0.2298 0.046 Uiso 1 1 calc R U . . .
H36B H 0.6690 0.2050 0.2106 0.046 Uiso 1 1 calc R U . . .
C37 C 0.4577(4) 0.11317(18) 0.11385(16) 0.0340(6) Uani 1 1 d . . . . .
H37 H 0.5592 0.1024 0.0855 0.041 Uiso 1 1 calc R U . . .
C38 C 0.4176(4) 0.35457(18) 0.18924(15) 0.0328(6) Uani 1 1 d . . . . .
C39 C 0.3617(4) 0.4265(2) 0.21814(16) 0.0391(6) Uani 1 1 d . . . . .
H39 H 0.317(5) 0.484(2) 0.2404(19) 0.047 Uiso 1 1 d . U . . .
C40 C 0.3653(4) 0.02150(19) 0.11015(17) 0.0377(6) Uani 1 1 d . . . . .
C41 C 0.2901(5) -0.0532(2) 0.1056(2) 0.0452(7) Uani 1 1 d . . . . .
H41 H 0.231(5) -0.115(3) 0.101(2) 0.054 Uiso 1 1 d . U . . .
C42 C -0.0978(3) 0.35159(16) 0.05170(14) 0.0250(5) Uani 1 1 d . . . . .
C43 C -0.1414(4) 0.42200(18) 0.11185(15) 0.0311(5) Uani 1 1 d . . . . .
H43 H -0.1158 0.4200 0.1600 0.037 Uiso 1 1 calc R U . . .
C44 C -0.2245(4) 0.49701(19) 0.10097(17) 0.0378(6) Uani 1 1 d . . . . .
H44 H -0.2529 0.5441 0.1423 0.045 Uiso 1 1 calc R U . . .
C45 C -0.2644(4) 0.50234(18) 0.03141(17) 0.0357(6) Uani 1 1 d . . . . .
H45 H -0.3172 0.5532 0.0257 0.043 Uiso 1 1 calc R U . . .
C46 C -0.2251(3) 0.43013(17) -0.03224(15) 0.0298(5) Uani 1 1 d . . . . .
C47 C -0.2651(4) 0.4294(2) -0.10654(17) 0.0373(6) Uani 1 1 d . . . . .
H47 H -0.3206 0.4778 -0.1157 0.045 Uiso 1 1 calc R U . . .
C48 C -0.2221(4) 0.3576(2) -0.16462(17) 0.0415(7) Uani 1 1 d . . . . .
H48 H -0.2467 0.3566 -0.2137 0.050 Uiso 1 1 calc R U . . .
C49 C -0.1400(4) 0.2853(2) -0.14903(16) 0.0390(6) Uani 1 1 d . . . . .
H49 H -0.1115 0.2366 -0.1892 0.047 Uiso 1 1 calc R U . . .
C50 C -0.1420(3) 0.35411(16) -0.02246(14) 0.0256(5) 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 1.361(3) . ?
F2 C32 1.372(3) . ?
O1 C1 1.224(3) . ?
O2 C26 1.219(3) . ?
N1 C24 1.327(3) . ?
N1 C25 1.364(4) . ?
N2 C1 1.358(3) . ?
N2 C17 1.403(3) . ?
N2 H2 0.89(3) . ?
N3 C49 1.323(3) . ?
N3 C50 1.365(3) . ?
N4 C26 1.366(3) . ?
N4 C42 1.399(3) . ?
N4 H4 0.85(3) . ?
C1 C2 1.519(3) . ?
C2 C3 1.543(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.513(3) . ?
C3 C10 1.567(3) . ?
C3 C12 1.586(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.397(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.373(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(4) . ?
C8 C9 1.393(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C13 1.457(3) . ?
C10 C11 1.549(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.551(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C15 1.456(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.175(4) . ?
C14 H14 0.90(4) . ?
C15 C16 1.184(4) . ?
C16 H16 0.94(3) . ?
C17 C18 1.369(4) . ?
C17 C25 1.436(3) . ?
C18 C19 1.412(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.355(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.416(4) . ?
C20 H20 0.9300 . ?
C21 C25 1.413(3) . ?
C21 C22 1.416(4) . ?
C22 C23 1.359(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.403(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C26 C27 1.517(3) . ?
C27 C28 1.543(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.513(3) . ?
C28 C35 1.567(3) . ?
C28 C37 1.581(3) . ?
C29 C34 1.388(3) . ?
C29 C30 1.394(3) . ?
C30 C31 1.385(4) . ?
C30 H30 0.9300 . ?
C31 C32 1.371(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.367(4) . ?
C33 C34 1.390(4) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C35 C38 1.456(4) . ?
C35 C36 1.551(4) . ?
C35 H35 0.9800 . ?
C36 C37 1.551(4) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C40 1.458(4) . ?
C37 H37 0.9800 . ?
C38 C39 1.182(4) . ?
C39 H39 0.94(3) . ?
C40 C41 1.177(4) . ?
C41 H41 0.96(4) . ?
C42 C43 1.376(3) . ?
C42 C50 1.431(3) . ?
C43 C44 1.406(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.361(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.417(4) . ?
C45 H45 0.9300 . ?
C46 C50 1.412(3) . ?
C46 C47 1.413(4) . ?
C47 C48 1.361(4) . ?
C47 H47 0.9300 . ?
C48 C49 1.403(4) . ?
C48 H48 0.9300 . ?
C49 H49 0.9300 . ?

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
C24 N1 C25 117.5(2) . . ?
C1 N2 C17 128.0(2) . . ?
C1 N2 H2 117.6(19) . . ?
C17 N2 H2 113.8(19) . . ?
C49 N3 C50 117.1(2) . . ?
C26 N4 C42 127.5(2) . . ?
C26 N4 H4 117(2) . . ?
C42 N4 H4 115(2) . . ?
O1 C1 N2 122.9(2) . . ?
O1 C1 C2 120.9(2) . . ?
N2 C1 C2 116.1(2) . . ?
C1 C2 C3 119.65(18) . . ?
C1 C2 H2A 107.4 . . ?
C3 C2 H2A 107.4 . . ?
C1 C2 H2B 107.4 . . ?
C3 C2 H2B 107.4 . . ?
H2A C2 H2B 106.9 . . ?
C4 C3 C2 113.08(18) . . ?
C4 C3 C10 117.36(18) . . ?
C2 C3 C10 113.82(19) . . ?
C4 C3 C12 115.02(18) . . ?
C2 C3 C12 108.70(17) . . ?
C10 C3 C12 85.82(16) . . ?
C5 C4 C9 118.3(2) . . ?
C5 C4 C3 122.2(2) . . ?
C9 C4 C3 119.5(2) . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 118.4(2) . . ?
C7 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
F1 C7 C8 118.5(2) . . ?
F1 C7 C6 118.2(2) . . ?
C8 C7 C6 123.3(2) . . ?
C7 C8 C9 117.5(2) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 H8 121.3 . . ?
C8 C9 C4 121.7(2) . . ?
C8 C9 H9 119.2 . . ?
C4 C9 H9 119.2 . . ?
C13 C10 C11 119.4(2) . . ?
C13 C10 C3 120.2(2) . . ?
C11 C10 C3 89.62(17) . . ?
C13 C10 H10 108.7 . . ?
C11 C10 H10 108.7 . . ?
C3 C10 H10 108.7 . . ?
C10 C11 C12 87.64(17) . . ?
C10 C11 H11A 114.0 . . ?
C12 C11 H11A 114.0 . . ?
C10 C11 H11B 114.0 . . ?
C12 C11 H11B 114.0 . . ?
H11A C11 H11B 111.2 . . ?
C15 C12 C11 118.1(2) . . ?
C15 C12 C3 119.92(19) . . ?
C11 C12 C3 88.84(17) . . ?
C15 C12 H12 109.5 . . ?
C11 C12 H12 109.5 . . ?
C3 C12 H12 109.5 . . ?
C14 C13 C10 179.0(3) . . ?
C13 C14 H14 173(2) . . ?
C16 C15 C12 177.5(3) . . ?
C15 C16 H16 177.2(19) . . ?
C18 C17 N2 125.7(2) . . ?
C18 C17 C25 119.7(2) . . ?
N2 C17 C25 114.6(2) . . ?
C17 C18 C19 119.8(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 122.0(3) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C25 C21 C22 116.8(3) . . ?
C25 C21 C20 119.3(3) . . ?
C22 C21 C20 124.0(3) . . ?
C23 C22 C21 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C21 C22 H22 120.1 . . ?
C22 C23 C24 119.3(3) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
N1 C24 C23 123.4(3) . . ?
N1 C24 H24 118.3 . . ?
C23 C24 H24 118.3 . . ?
N1 C25 C21 123.2(2) . . ?
N1 C25 C17 117.4(2) . . ?
C21 C25 C17 119.4(2) . . ?
O2 C26 N4 122.6(2) . . ?
O2 C26 C27 121.1(2) . . ?
N4 C26 C27 116.2(2) . . ?
C26 C27 C28 119.09(19) . . ?
C26 C27 H27A 107.5 . . ?
C28 C27 H27A 107.5 . . ?
C26 C27 H27B 107.5 . . ?
C28 C27 H27B 107.5 . . ?
H27A C27 H27B 107.0 . . ?
C29 C28 C27 112.8(2) . . ?
C29 C28 C35 117.6(2) . . ?
C27 C28 C35 112.9(2) . . ?
C29 C28 C37 115.7(2) . . ?
C27 C28 C37 109.09(19) . . ?
C35 C28 C37 85.91(18) . . ?
C34 C29 C30 118.2(2) . . ?
C34 C29 C28 119.0(2) . . ?
C30 C29 C28 122.7(2) . . ?
C31 C30 C29 121.2(2) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C32 C31 C30 118.0(2) . . ?
C32 C31 H31 121.0 . . ?
C30 C31 H31 121.0 . . ?
C33 C32 C31 123.4(3) . . ?
C33 C32 F2 118.1(2) . . ?
C31 C32 F2 118.5(3) . . ?
C32 C33 C34 117.7(2) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 H33 121.2 . . ?
C29 C34 C33 121.5(2) . . ?
C29 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C38 C35 C36 121.4(2) . . ?
C38 C35 C28 119.1(2) . . ?
C36 C35 C28 88.83(18) . . ?
C38 C35 H35 108.6 . . ?
C36 C35 H35 108.6 . . ?
C28 C35 H35 108.6 . . ?
C35 C36 C37 87.5(2) . . ?
C35 C36 H36A 114.1 . . ?
C37 C36 H36A 114.1 . . ?
C35 C36 H36B 114.1 . . ?
C37 C36 H36B 114.1 . . ?
H36A C36 H36B 111.3 . . ?
C40 C37 C36 120.8(3) . . ?
C40 C37 C28 119.1(2) . . ?
C36 C37 C28 88.32(18) . . ?
C40 C37 H37 108.9 . . ?
C36 C37 H37 108.9 . . ?
C28 C37 H37 108.9 . . ?
C39 C38 C35 177.3(3) . . ?
C38 C39 H39 179(2) . . ?
C41 C40 C37 178.7(3) . . ?
C40 C41 H41 178(2) . . ?
C43 C42 N4 124.8(2) . . ?
C43 C42 C50 119.4(2) . . ?
N4 C42 C50 115.8(2) . . ?
C42 C43 C44 120.4(2) . . ?
C42 C43 H43 119.8 . . ?
C44 C43 H43 119.8 . . ?
C45 C44 C43 121.5(2) . . ?
C45 C44 H44 119.2 . . ?
C43 C44 H44 119.2 . . ?
C44 C45 C46 119.8(2) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C50 C46 C47 117.1(2) . . ?
C50 C46 C45 119.5(2) . . ?
C47 C46 C45 123.4(2) . . ?
C48 C47 C46 119.8(2) . . ?
C48 C47 H47 120.1 . . ?
C46 C47 H47 120.1 . . ?
C47 C48 C49 118.7(3) . . ?
C47 C48 H48 120.6 . . ?
C49 C48 H48 120.6 . . ?
N3 C49 C48 124.3(3) . . ?
N3 C49 H49 117.9 . . ?
C48 C49 H49 117.9 . . ?
N3 C50 C46 123.0(2) . . ?
N3 C50 C42 117.5(2) . . ?
C46 C50 C42 119.4(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 N1 0.89(3) 2.19(3) 2.649(3) 111(2) .
N4 H4 N3 0.85(3) 2.28(3) 2.671(3) 108(2) .

_refine_diff_density_max         0.348
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.056



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/cyclohexane'
_chemical_properties_physical    
', Air-sensitive,Moisture-sensitive,Heat-sensitive,Oxygen-sensitive,Light-sensitive,Photo-sensitive'
####################################################################### 
# 
# 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_exp_8018
_database_code_depnum_ccdc_archive 'CCDC 1524151'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-01-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        4
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 F N2 O'
_chemical_formula_weight         334.38

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'
F F 0.0171 0.0103 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.4896(12)
_cell_length_b                   14.7995(18)
_cell_length_c                   12.088(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.000(11)
_cell_angle_gamma                90
_cell_volume                     1697.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5872
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.078
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3317
_reflns_number_gt                2422
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (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)+(0.0549P)²+0.0310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0982
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 -0.11704(10) 0.15061(6) -0.03989(9) 0.0524(3) Uani 1 1 d . . . . .
N1 N 0.38057(13) 0.40016(9) -0.03311(11) 0.0319(3) Uani 1 1 d . . . . .
O1 O 0.25823(12) 0.52231(7) 0.02470(10) 0.0457(3) Uani 1 1 d . . . . .
C2 C 0.47355(14) 0.35563(9) -0.20703(13) 0.0283(3) Uani 1 1 d . . . . .
N2 N 0.54732(12) 0.29197(8) -0.14844(11) 0.0333(3) Uani 1 1 d . . . . .
C10 C 0.32122(14) 0.45243(10) 0.04597(14) 0.0311(4) Uani 1 1 d . . . . .
C1 C 0.38306(14) 0.41419(9) -0.14722(13) 0.0292(4) Uani 1 1 d . . . . .
C12 C 0.19655(14) 0.39717(10) 0.21811(13) 0.0292(4) Uani 1 1 d . . . . .
C17 C 0.01875(14) 0.36104(10) 0.06711(14) 0.0325(4) Uani 1 1 d . . . . .
H17 H 0.0086 0.4241 0.0544 0.039 Uiso 1 1 calc R U . . .
C16 C 0.11057(14) 0.33144(9) 0.15029(13) 0.0274(3) Uani 1 1 d . . . . .
C19 C -0.04202(15) 0.21092(10) 0.02325(14) 0.0349(4) Uani 1 1 d . . . . .
C13 C 0.12128(16) 0.48432(11) 0.25734(14) 0.0373(4) Uani 1 1 d . . . . .
H13A H 0.1522 0.5398 0.2189 0.045 Uiso 1 1 calc R U . . .
H13B H 0.0172 0.4796 0.2567 0.045 Uiso 1 1 calc R U . . .
C11 C 0.33789(15) 0.41715(10) 0.16208(13) 0.0319(4) Uani 1 1 d . . . . .
H11A H 0.3907 0.4621 0.2071 0.038 Uiso 1 1 calc R U . . .
H11B H 0.3945 0.3610 0.1606 0.038 Uiso 1 1 calc R U . . .
C6 C 0.48409(15) 0.36492(10) -0.32267(14) 0.0338(4) Uani 1 1 d . . . . .
C21 C 0.12181(15) 0.23885(10) 0.16780(14) 0.0331(4) Uani 1 1 d . . . . .
H21 H 0.1835 0.2171 0.2245 0.040 Uiso 1 1 calc R U . . .
C8 C 0.31624(18) 0.48573(11) -0.31857(16) 0.0428(5) Uani 1 1 d . . . . .
H8 H 0.2615 0.5301 -0.3564 0.051 Uiso 1 1 calc R U . . .
C18 C -0.05815(15) 0.30113(11) 0.00252(14) 0.0357(4) Uani 1 1 d . . . . .
H18 H -0.1202 0.3220 -0.0545 0.043 Uiso 1 1 calc R U . . .
C9 C 0.30500(16) 0.47784(10) -0.20301(15) 0.0367(4) Uani 1 1 d . . . . .
H9 H 0.2435 0.5165 -0.1639 0.044 Uiso 1 1 calc R U . . .
C20 C 0.04528(16) 0.17775(10) 0.10466(15) 0.0373(4) Uani 1 1 d . . . . .
H20 H 0.0531 0.1146 0.1174 0.045 Uiso 1 1 calc R U . . .
C3 C 0.63145(16) 0.23882(11) -0.20399(16) 0.0408(4) Uani 1 1 d . . . . .
H3 H 0.6835 0.1945 -0.1637 0.049 Uiso 1 1 calc R U . . .
C7 C 0.40275(17) 0.43187(11) -0.37734(15) 0.0419(4) Uani 1 1 d . . . . .
H7 H 0.4087 0.4391 -0.4552 0.050 Uiso 1 1 calc R U . . .
C15 C 0.22473(17) 0.37329(11) 0.34152(14) 0.0372(4) Uani 1 1 d . . . . .
H15A H 0.1581 0.3283 0.3714 0.045 Uiso 1 1 calc R U . . .
H15B H 0.3235 0.3559 0.3583 0.045 Uiso 1 1 calc R U . . .
C5 C 0.57604(17) 0.30573(12) -0.37722(15) 0.0434(4) Uani 1 1 d . . . . .
H5 H 0.5865 0.3098 -0.4551 0.052 Uiso 1 1 calc R U . . .
C4 C 0.64954(18) 0.24305(12) -0.31842(17) 0.0469(5) Uani 1 1 d . . . . .
H4 H 0.7121 0.2028 -0.3542 0.056 Uiso 1 1 calc R U . . .
C14 C 0.18970(18) 0.47159(11) 0.37283(15) 0.0418(4) Uani 1 1 d . . . . .
H14A H 0.1226 0.4769 0.4343 0.050 Uiso 1 1 calc R U . . .
H14B H 0.2738 0.5099 0.3862 0.050 Uiso 1 1 calc R U . . .
H1 H 0.4315(16) 0.3545(11) -0.0126(14) 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
F1 C19 1.3665(17) . ?
N1 C10 1.359(2) . ?
N1 C1 1.395(2) . ?
N1 H1 0.865(16) . ?
O1 C10 1.2197(18) . ?
C2 N2 1.3645(19) . ?
C2 C6 1.410(2) . ?
C2 C1 1.426(2) . ?
N2 C3 1.314(2) . ?
C10 C11 1.503(2) . ?
C1 C9 1.369(2) . ?
C12 C16 1.504(2) . ?
C12 C11 1.542(2) . ?
C12 C15 1.552(2) . ?
C12 C13 1.553(2) . ?
C17 C18 1.381(2) . ?
C17 C16 1.390(2) . ?
C17 H17 0.9500 . ?
C16 C21 1.390(2) . ?
C19 C20 1.366(2) . ?
C19 C18 1.366(2) . ?
C13 C14 1.541(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C6 C5 1.408(2) . ?
C6 C7 1.413(2) . ?
C21 C20 1.381(2) . ?
C21 H21 0.9500 . ?
C8 C7 1.354(3) . ?
C8 C9 1.408(2) . ?
C8 H8 0.9500 . ?
C18 H18 0.9500 . ?
C9 H9 0.9500 . ?
C20 H20 0.9500 . ?
C3 C4 1.398(3) . ?
C3 H3 0.9500 . ?
C7 H7 0.9500 . ?
C15 C14 1.541(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C5 C4 1.355(2) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 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
C10 N1 C1 128.66(14) . . ?
C10 N1 H1 118.7(11) . . ?
C1 N1 H1 112.4(11) . . ?
N2 C2 C6 122.50(14) . . ?
N2 C2 C1 117.69(14) . . ?
C6 C2 C1 119.82(13) . . ?
C3 N2 C2 117.32(15) . . ?
O1 C10 N1 122.80(16) . . ?
O1 C10 C11 122.32(15) . . ?
N1 C10 C11 114.88(13) . . ?
C9 C1 N1 124.83(15) . . ?
C9 C1 C2 119.61(15) . . ?
N1 C1 C2 115.56(13) . . ?
C16 C12 C11 110.65(13) . . ?
C16 C12 C15 117.36(12) . . ?
C11 C12 C15 109.23(11) . . ?
C16 C12 C13 117.12(11) . . ?
C11 C12 C13 112.54(12) . . ?
C15 C12 C13 88.17(12) . . ?
C18 C17 C16 121.66(14) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C16 C21 117.79(13) . . ?
C17 C16 C12 121.19(12) . . ?
C21 C16 C12 121.01(12) . . ?
C20 C19 C18 123.21(14) . . ?
C20 C19 F1 118.09(13) . . ?
C18 C19 F1 118.69(13) . . ?
C14 C13 C12 89.22(11) . . ?
C14 C13 H13A 113.8 . . ?
C12 C13 H13A 113.8 . . ?
C14 C13 H13B 113.8 . . ?
C12 C13 H13B 113.8 . . ?
H13A C13 H13B 111.0 . . ?
C10 C11 C12 113.49(12) . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C5 C6 C2 117.31(15) . . ?
C5 C6 C7 123.72(16) . . ?
C2 C6 C7 118.97(15) . . ?
C20 C21 C16 121.53(14) . . ?
C20 C21 H21 119.2 . . ?
C16 C21 H21 119.2 . . ?
C7 C8 C9 121.92(15) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C19 C18 C17 117.84(14) . . ?
C19 C18 H18 121.1 . . ?
C17 C18 H18 121.1 . . ?
C1 C9 C8 119.76(16) . . ?
C1 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C19 C20 C21 117.96(14) . . ?
C19 C20 H20 121.0 . . ?
C21 C20 H20 121.0 . . ?
N2 C3 C4 124.40(16) . . ?
N2 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C8 C7 C6 119.91(17) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C14 C15 C12 89.24(12) . . ?
C14 C15 H15A 113.8 . . ?
C12 C15 H15A 113.8 . . ?
C14 C15 H15B 113.8 . . ?
C12 C15 H15B 113.8 . . ?
H15A C15 H15B 111.0 . . ?
C4 C5 C6 119.86(17) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C5 C4 C3 118.61(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C13 C14 C15 88.98(12) . . ?
C13 C14 H14A 113.8 . . ?
C15 C14 H14A 113.8 . . ?
C13 C14 H14B 113.8 . . ?
C15 C14 H14B 113.8 . . ?
H14A C14 H14B 111.0 . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EA/cyclohexane'
