# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1561488'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_audit_creation_date             2017-07-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O2'
_chemical_formula_sum            'C18 H15 N O2'
_chemical_formula_weight         277.31
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1284(12)
_cell_length_b                   10.938(2)
_cell_length_c                   11.925(2)
_cell_angle_alpha                114.20(3)
_cell_angle_beta                 90.94(3)
_cell_angle_gamma                91.43(3)
_cell_volume                     728.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.7178
_cell_measurement_theta_min      2.0424
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8714
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.745
_diffrn_reflns_theta_min         1.873
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2607
_reflns_number_total             3374
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.239
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1209
_refine_ls_R_factor_gt           0.0967
_refine_ls_restrained_S_all      1.239
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0830P)²+0.5310P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2441
_refine_ls_wR_factor_ref         0.2591
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00K(H00D,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00L(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O001 O 0.5789(5) 0.0576(3) 0.3008(2) 0.0646(8) Uani 1 1 d . . . . .
N002 N 0.3811(4) 0.4468(3) 0.8534(2) 0.0422(7) Uani 1 1 d . . . . .
O003 O 0.2515(5) -0.0387(3) 0.3076(2) 0.0726(9) Uani 1 1 d . . . . .
C004 C 0.2418(5) 0.5551(3) 0.9073(3) 0.0390(7) Uani 1 1 d . . . . .
C005 C 0.3823(5) 0.3465(3) 0.7278(3) 0.0390(7) Uani 1 1 d . . . . .
C006 C 0.3953(6) 0.1506(3) 0.4871(3) 0.0436(8) Uani 1 1 d . . . . .
C007 C 0.2971(5) 0.6232(3) 1.0329(3) 0.0418(7) Uani 1 1 d . . . . .
H007 H 0.231631 0.698220 1.089897 0.050 Uiso 1 1 calc R . . . .
C008 C 0.5254(5) 0.4468(3) 0.9451(3) 0.0415(7) Uani 1 1 d . . . . .
C009 C 0.5722(6) 0.3313(3) 0.6623(3) 0.0470(8) Uani 1 1 d . . . . .
H009 H 0.694830 0.385946 0.698823 0.056 Uiso 1 1 calc R . . . .
C00A C -0.1198(6) 0.6508(3) 0.8952(3) 0.0472(8) Uani 1 1 d . . . . .
H00A H -0.143064 0.659812 0.975045 0.057 Uiso 1 1 calc R . . . .
C00B C 0.2063(6) 0.1661(3) 0.5545(3) 0.0501(8) Uani 1 1 d . . . . .
H00B H 0.084013 0.110757 0.518752 0.060 Uiso 1 1 calc R . . . .
C00C C 0.5798(6) 0.2342(3) 0.5415(3) 0.0477(8) Uani 1 1 d . . . . .
H00C H 0.706534 0.225065 0.497369 0.057 Uiso 1 1 calc R . . . .
C00D C 0.0752(6) 0.5945(3) 0.8374(3) 0.0436(8) Uani 1 1 d . . . . .
C00E C 0.3971(7) 0.0454(3) 0.3570(3) 0.0511(9) Uani 1 1 d . . . . .
C00F C 0.1981(6) 0.2631(4) 0.6744(3) 0.0492(8) Uani 1 1 d . . . . .
H00F H 0.071412 0.272525 0.718606 0.059 Uiso 1 1 calc R . . . .
C00G C -0.2766(6) 0.6926(4) 0.8353(4) 0.0558(9) Uani 1 1 d . . . . .
H00G H -0.403116 0.729982 0.875399 0.067 Uiso 1 1 calc R . . . .
C00H C 0.1062(6) 0.5854(4) 0.7168(3) 0.0508(9) Uani 1 1 d . . . . .
H00H H 0.234209 0.550896 0.676752 0.061 Uiso 1 1 calc R . . . .
C00I C -0.0552(7) 0.6282(4) 0.6575(3) 0.0589(10) Uani 1 1 d . . . . .
H00I H -0.032901 0.622122 0.578427 0.071 Uiso 1 1 calc R . . . .
C00J C -0.2468(7) 0.6793(4) 0.7152(4) 0.0597(10) Uani 1 1 d . . . . .
H00J H -0.355091 0.704660 0.674285 0.072 Uiso 1 1 calc R . . . .
C00K C 0.6000(9) -0.0341(4) 0.1709(3) 0.0735(13) Uani 1 1 d . . . . .
H00D H 0.469032 -0.034463 0.123996 0.088 Uiso 1 1 calc R . . . .
H00E H 0.621614 -0.124671 0.163408 0.088 Uiso 1 1 calc R . . . .
C00L C 0.7926(9) 0.0151(5) 0.1245(4) 0.0926(17) Uani 1 1 d . . . . .
H00K H 0.811182 -0.042287 0.039431 0.139 Uiso 1 1 calc GR . . . .
H00L H 0.921091 0.014491 0.171346 0.139 Uiso 1 1 calc GR . . . .
H00M H 0.769425 0.104898 0.132800 0.139 Uiso 1 1 calc GR . . . .


_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
O001 C00E 1.342(5) . ?
O001 C00K 1.470(4) . ?
N002 C004 1.411(4) . ?
N002 C005 1.449(4) . ?
N002 C008 1.396(4) . ?
O003 C00E 1.219(4) . ?
C004 C007 1.403(4) . ?
C004 C00D 1.487(4) . ?
C005 C009 1.388(5) . ?
C005 C00F 1.400(5) . ?
C006 C00B 1.394(5) . ?
C006 C00C 1.405(5) . ?
C006 C00E 1.506(4) . ?
C007 H007 0.9300 . ?
C007 C008 1.426(4) 2_667 ?
C008 C008 1.395(6) 2_667 ?
C009 H009 0.9300 . ?
C009 C00C 1.398(4) . ?
C00A H00A 0.9300 . ?
C00A C00D 1.414(5) . ?
C00A C00G 1.383(5) . ?
C00B H00B 0.9300 . ?
C00B C00F 1.391(5) . ?
C00C H00C 0.9300 . ?
C00D C00H 1.417(5) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00G C00J 1.394(5) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.404(5) . ?
C00I H00I 0.9300 . ?
C00I C00J 1.382(6) . ?
C00J H00J 0.9300 . ?
C00K H00D 0.9700 . ?
C00K H00E 0.9700 . ?
C00K C00L 1.491(7) . ?
C00L H00K 0.9600 . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?

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
C00E O001 C00K 117.6(3) . . ?
C004 N002 C005 129.4(3) . . ?
C008 N002 C004 107.8(2) . . ?
C008 N002 C005 122.7(3) . . ?
N002 C004 C00D 124.1(3) . . ?
C007 C004 N002 109.3(3) . . ?
C007 C004 C00D 126.4(3) . . ?
C009 C005 N002 118.8(3) . . ?
C009 C005 C00F 120.3(3) . . ?
C00F C005 N002 120.9(3) . . ?
C00B C006 C00C 119.4(3) . . ?
C00B C006 C00E 119.4(3) . . ?
C00C C006 C00E 121.3(3) . . ?
C004 C007 H007 127.2 . . ?
C004 C007 C008 105.6(3) . 2_667 ?
C008 C007 H007 127.2 2_667 . ?
N002 C008 C007 142.8(3) . 2_667 ?
C008 C008 N002 107.8(3) 2_667 . ?
C008 C008 C007 109.4(3) 2_667 2_667 ?
C005 C009 H009 119.9 . . ?
C005 C009 C00C 120.2(3) . . ?
C00C C009 H009 119.9 . . ?
C00D C00A H00A 119.4 . . ?
C00G C00A H00A 119.4 . . ?
C00G C00A C00D 121.2(3) . . ?
C006 C00B H00B 119.5 . . ?
C00F C00B C006 120.9(3) . . ?
C00F C00B H00B 119.5 . . ?
C006 C00C H00C 120.1 . . ?
C009 C00C C006 119.8(3) . . ?
C009 C00C H00C 120.1 . . ?
C00A C00D C004 119.1(3) . . ?
C00A C00D C00H 117.5(3) . . ?
C00H C00D C004 123.3(3) . . ?
O001 C00E C006 111.1(3) . . ?
O003 C00E O001 123.9(3) . . ?
O003 C00E C006 124.9(4) . . ?
C005 C00F H00F 120.3 . . ?
C00B C00F C005 119.4(3) . . ?
C00B C00F H00F 120.3 . . ?
C00A C00G H00G 119.7 . . ?
C00A C00G C00J 120.6(4) . . ?
C00J C00G H00G 119.7 . . ?
C00D C00H H00H 119.8 . . ?
C00I C00H C00D 120.3(3) . . ?
C00I C00H H00H 119.8 . . ?
C00H C00I H00I 119.6 . . ?
C00J C00I C00H 120.7(3) . . ?
C00J C00I H00I 119.6 . . ?
C00G C00J H00J 120.2 . . ?
C00I C00J C00G 119.5(3) . . ?
C00I C00J H00J 120.2 . . ?
O001 C00K H00D 110.3 . . ?
O001 C00K H00E 110.3 . . ?
O001 C00K C00L 107.0(4) . . ?
H00D C00K H00E 108.6 . . ?
C00L C00K H00D 110.3 . . ?
C00L C00K H00E 110.3 . . ?
C00K C00L H00K 109.5 . . ?
C00K C00L H00L 109.5 . . ?
C00K C00L H00M 109.5 . . ?
H00K C00L H00L 109.5 . . ?
H00K C00L H00M 109.5 . . ?
H00L C00L H00M 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
N002 C004 C007 C008 -0.2(3) . . . 2_667 ?
N002 C004 C00D C00A 148.0(3) . . . . ?
N002 C004 C00D C00H -35.7(5) . . . . ?
N002 C005 C009 C00C 179.1(3) . . . . ?
N002 C005 C00F C00B -178.7(3) . . . . ?
C004 N002 C005 C009 123.5(4) . . . . ?
C004 N002 C005 C00F -58.5(5) . . . . ?
C004 N002 C008 C007 179.5(4) . . . 2_667 ?
C004 N002 C008 C008 0.6(4) . . . 2_667 ?
C004 C00D C00H C00I -178.0(3) . . . . ?
C005 N002 C004 C007 178.0(3) . . . . ?
C005 N002 C004 C00D -6.2(5) . . . . ?
C005 N002 C008 C007 1.1(7) . . . 2_667 ?
C005 N002 C008 C008 -177.8(3) . . . 2_667 ?
C005 C009 C00C C006 -0.9(5) . . . . ?
C006 C00B C00F C005 0.2(5) . . . . ?
C007 C004 C00D C00A -37.0(5) . . . . ?
C007 C004 C00D C00H 139.4(4) . . . . ?
C008 N002 C004 C007 -0.3(4) . . . . ?
C008 N002 C004 C00D 175.5(3) . . . . ?
C008 N002 C005 C009 -58.5(4) . . . . ?
C008 N002 C005 C00F 119.5(4) . . . . ?
C009 C005 C00F C00B -0.8(5) . . . . ?
C00A C00D C00H C00I -1.6(5) . . . . ?
C00A C00G C00J C00I -2.3(6) . . . . ?
C00B C006 C00C C009 0.3(5) . . . . ?
C00B C006 C00E O001 171.0(3) . . . . ?
C00B C006 C00E O003 -7.7(5) . . . . ?
C00C C006 C00B C00F 0.1(5) . . . . ?
C00C C006 C00E O001 -8.5(4) . . . . ?
C00C C006 C00E O003 172.9(4) . . . . ?
C00D C004 C007 C008 -175.8(3) . . . 2_667 ?
C00D C00A C00G C00J 0.5(5) . . . . ?
C00D C00H C00I C00J -0.2(6) . . . . ?
C00E O001 C00K C00L 170.0(4) . . . . ?
C00E C006 C00B C00F -179.3(3) . . . . ?
C00E C006 C00C C009 179.7(3) . . . . ?
C00F C005 C009 C00C 1.2(5) . . . . ?
C00G C00A C00D C004 178.0(3) . . . . ?
C00G C00A C00D C00H 1.4(5) . . . . ?
C00H C00I C00J C00G 2.2(6) . . . . ?
C00K O001 C00E O003 1.5(6) . . . . ?
C00K O001 C00E C006 -177.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_hy
_database_code_depnum_ccdc_archive 'CCDC 1561489'
_audit_update_record             
;
2017-07-11 deposited with the CCDC.
2017-08-31 downloaded from the CCDC.
;
_audit_creation_date             2017-07-11
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.06.29 svn.r3433 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F3 N O2'
_chemical_formula_sum            'C19 H14 F3 N O2'
_chemical_formula_weight         345.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     st
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'
F F 0.0727 0.0534 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.1875(3)
_cell_length_b                   12.1177(5)
_cell_length_c                   12.2490(5)
_cell_angle_alpha                63.176(4)
_cell_angle_beta                 88.118(4)
_cell_angle_gamma                81.174(4)
_cell_volume                     809.19(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5625
_cell_measurement_temperature    285.00(10)
_cell_measurement_theta_max      72.3970
_cell_measurement_theta_min      6.9800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.987
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             356
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7514
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        64.996
_diffrn_reflns_theta_max         64.996
_diffrn_reflns_theta_min         4.048
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      285.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  96.00   0.50    0.50    --   45.70  19.00  60.00  210
  2  ω    102.00 131.00   0.50    0.50    --   45.70  19.00  60.00   58
  3  ω     96.00 131.00   0.50    0.50    --   45.70  82.00  90.00   70
  4  ω    144.00 170.00   0.50    0.50    --   99.80  82.00   0.00   52
  5  ω    109.00 183.00   0.50    0.50    --   99.80  15.00 120.00  148
  6  ω     93.00 119.00   0.50    0.50    --   99.80 -82.00-120.00   52
  7  ω     95.00 128.00   0.50    0.50    --   99.80 -61.00 -90.00   66
  8  ω     74.00 100.00   0.50    0.50    --   99.80 -82.00-150.00   52
  9  ω     77.00 103.00   0.50    0.50    --   99.80 -82.00 -30.00   52
 10  ω     70.00 122.00   0.50    0.50    --   99.80 -82.00   0.00  104
 11  ω     84.00 117.00   0.50    0.50    --   99.80 -82.00 150.00   66
 12  ω     28.00 124.00   0.50    0.50    --   99.80 -61.00  90.00  192
 13  ω     89.00 184.00   0.50    0.50    --   99.80  15.00-150.00  190
 14  ω     87.00 134.00   0.50    0.50    --   99.80  82.00-150.00   94
 15  ω     10.00  85.00   0.50    0.50    --   99.80  15.00-150.00  150
 16  ω     15.00 121.00   0.50    0.50    --   99.80 -61.00 -30.00  212
 17  ω     22.00  59.00   0.50    0.50    --   45.70 -82.00  60.00   74
 18  ω     10.00 143.50   0.50    0.50    --   99.80 -82.00  90.00  267
 19  ω     22.00  72.00   0.50    0.50    --   99.80  15.00 120.00  100
 20  ω     12.00 109.00   0.50    0.50    --   99.80 -82.00 -90.00  194
 21  ω     13.00  73.00   0.50    0.50    --   99.80 -82.00-180.00  120
 22  ω     22.00  89.00   0.50    0.50    --   99.80 -61.00 -90.00  134
 23  ω    -34.00  42.00   0.50    0.50    --   45.70 -82.00 120.00  152
 24  ω    -43.00  83.00   0.50    0.50    --   45.70 -57.00-180.00  252
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0557158000
_diffrn_orient_matrix_UB_12      -0.0045750000
_diffrn_orient_matrix_UB_13      -0.1215440000
_diffrn_orient_matrix_UB_21      0.1704965000
_diffrn_orient_matrix_UB_22      0.0874618000
_diffrn_orient_matrix_UB_23      -0.0223639000
_diffrn_orient_matrix_UB_31      0.1772563000
_diffrn_orient_matrix_UB_32      -0.1145761000
_diffrn_orient_matrix_UB_33      0.0679983000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2546
_reflns_number_total             2722
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1170P)²+0.2870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-C0AA
 1.5 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C11(H11), C12(H12), C14(H14), C16(H16), C20(H20),
 C2AA(H2AA)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C2 C 0.0908(3) 0.60302(17) 0.73150(16) 0.0381(4) Uani 1 1 d . . . . .
C5 C 0.2790(3) 0.57457(19) 0.67876(19) 0.0468(5) Uani 1 1 d . . . . .
H5 H 0.410941 0.541471 0.724159 0.056 Uiso 1 1 calc R . . . .
C6 C 0.5528(3) 0.72503(18) 0.90403(18) 0.0426(5) Uani 1 1 d . . . . .
H6 H 0.598398 0.660116 0.980830 0.051 Uiso 1 1 calc R . . . .
C7 C 0.6065(3) 0.91891(19) 0.73490(19) 0.0463(5) Uani 1 1 d . . . . .
C9 C 0.2988(3) 0.82226(19) 0.73129(19) 0.0472(5) Uani 1 1 d . . . . .
H9 H 0.174746 0.822188 0.690495 0.057 Uiso 1 1 calc R . . . .
C11 C -0.1062(3) 0.6509(2) 0.66453(18) 0.0448(5) Uani 1 1 d . . . . .
H11 H -0.232449 0.668804 0.700634 0.054 Uiso 1 1 calc R . . . .
C12 C 0.4181(4) 0.9188(2) 0.67684(19) 0.0503(5) Uani 1 1 d . . . . .
H12 H 0.372079 0.984574 0.600544 0.060 Uiso 1 1 calc R . . . .
C13 C 0.0731(3) 0.64505(18) 0.49002(18) 0.0452(5) Uani 1 1 d . . . . .
C14 C -0.1150(3) 0.6722(2) 0.54401(19) 0.0487(5) Uani 1 1 d . . . . .
H14 H -0.247270 0.704701 0.498886 0.058 Uiso 1 1 calc R . . . .
C15 C 0.3618(3) 0.72399(17) 0.84740(17) 0.0391(4) Uani 1 1 d . . . . .
C16 C 0.6749(3) 0.8202(2) 0.84846(19) 0.0463(5) Uani 1 1 d . . . . .
H16 H 0.803318 0.818531 0.886952 0.056 Uiso 1 1 calc R . . . .
O17 O 0.2212(3) 0.63683(19) 0.31008(16) 0.0768(6) Uani 1 1 d . . . . .
O19 O -0.1183(4) 0.73379(19) 0.30242(15) 0.0770(6) Uani 1 1 d . . . . .
C20 C 0.2691(4) 0.5957(2) 0.55816(19) 0.0497(5) Uani 1 1 d . . . . .
H20 H 0.395031 0.576729 0.522489 0.060 Uiso 1 1 calc R . . . .
C21 C 0.0708(4) 0.6692(2) 0.3592(2) 0.0562(6) Uani 1 1 d . . . . .
N1AA N 0.0955(3) 0.58153(15) 0.85602(14) 0.0400(4) Uani 1 1 d . . . . .
C2AA C 0.1854(3) 0.57600(17) 1.03692(16) 0.0403(4) Uani 1 1 d . . . . .
H2AA H 0.249260 0.590556 1.095924 0.048 Uiso 1 1 calc R . . . .
C8 C 0.2260(3) 0.62676(17) 0.91352(17) 0.0394(4) Uani 1 1 d . . . . .
C3AA C -0.0274(3) 0.50234(17) 0.94490(16) 0.0381(4) Uani 1 1 d . . . . .
F4AA F 0.8714(4) 1.0317(2) 0.74884(18) 0.1055(7) Uani 1 1 d . . . . .
C3 C 0.7315(4) 1.0251(2) 0.6746(2) 0.0603(6) Uani 1 1 d . . . . .
F1 F 0.8541(3) 1.01751(17) 0.58530(15) 0.0875(6) Uani 1 1 d . . . . .
F2 F 0.6030(3) 1.13399(15) 0.6213(3) 0.1247(10) Uani 1 1 d . . . . .
C1 C -0.2953(14) 0.8785(6) 0.1192(4) 0.216(4) Uani 1 1 d D . . . .
H1A H -0.301715 0.908451 0.032078 0.324 Uiso 1 1 calc GR . . . .
H1B H -0.254324 0.941533 0.137921 0.324 Uiso 1 1 calc GR . . . .
H1C H -0.436338 0.859989 0.150951 0.324 Uiso 1 1 calc GR . . . .
C0AA C -0.1401(8) 0.7698(3) 0.1728(3) 0.1048(13) Uani 1 1 d D . . . .
H0AA H -0.000381 0.785379 0.135238 0.126 Uiso 1 1 calc R . . . .
H0AB H -0.187119 0.703056 0.160927 0.126 Uiso 1 1 calc R . . . .


_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
C2 C5 1.386(3) . ?
C2 C11 1.383(3) . ?
C2 N1AA 1.427(2) . ?
C5 H5 0.9300 . ?
C5 C20 1.382(3) . ?
C6 H6 0.9300 . ?
C6 C15 1.394(3) . ?
C6 C16 1.375(3) . ?
C7 C12 1.386(3) . ?
C7 C16 1.388(3) . ?
C7 C3 1.487(3) . ?
C9 H9 0.9300 . ?
C9 C12 1.374(3) . ?
C9 C15 1.399(3) . ?
C11 H11 0.9300 . ?
C11 C14 1.381(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(3) . ?
C13 C20 1.385(3) . ?
C13 C21 1.493(3) . ?
C14 H14 0.9300 . ?
C15 C8 1.466(3) . ?
C16 H16 0.9300 . ?
O17 C21 1.203(3) . ?
O19 C21 1.322(3) . ?
O19 C0AA 1.449(3) . ?
C20 H20 0.9300 . ?
N1AA C8 1.404(2) . ?
N1AA C3AA 1.382(2) . ?
C2AA H2AA 0.9300 . ?
C2AA C8 1.382(3) . ?
C2AA C3AA 1.409(3) 2_567 ?
C3AA C3AA 1.377(4) 2_567 ?
F4AA C3 1.312(3) . ?
C3 F1 1.339(3) . ?
C3 F2 1.317(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C0AA 1.401(5) . ?
C0AA H0AA 0.9700 . ?
C0AA H0AB 0.9700 . ?

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
C5 C2 N1AA 120.83(17) . . ?
C11 C2 C5 120.33(18) . . ?
C11 C2 N1AA 118.83(16) . . ?
C2 C5 H5 120.2 . . ?
C20 C5 C2 119.51(19) . . ?
C20 C5 H5 120.2 . . ?
C15 C6 H6 119.4 . . ?
C16 C6 H6 119.4 . . ?
C16 C6 C15 121.23(18) . . ?
C12 C7 C16 119.54(19) . . ?
C12 C7 C3 119.4(2) . . ?
C16 C7 C3 121.1(2) . . ?
C12 C9 H9 119.6 . . ?
C12 C9 C15 120.79(19) . . ?
C15 C9 H9 119.6 . . ?
C2 C11 H11 120.0 . . ?
C14 C11 C2 119.91(18) . . ?
C14 C11 H11 120.0 . . ?
C7 C12 H12 119.8 . . ?
C9 C12 C7 120.40(19) . . ?
C9 C12 H12 119.8 . . ?
C14 C13 C21 121.7(2) . . ?
C20 C13 C14 119.53(19) . . ?
C20 C13 C21 118.77(19) . . ?
C11 C14 C13 120.18(19) . . ?
C11 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C6 C15 C9 118.02(18) . . ?
C6 C15 C8 119.73(16) . . ?
C9 C15 C8 122.10(17) . . ?
C6 C16 C7 119.98(18) . . ?
C6 C16 H16 120.0 . . ?
C7 C16 H16 120.0 . . ?
C21 O19 C0AA 117.2(2) . . ?
C5 C20 C13 120.54(19) . . ?
C5 C20 H20 119.7 . . ?
C13 C20 H20 119.7 . . ?
O17 C21 C13 125.2(2) . . ?
O17 C21 O19 123.7(2) . . ?
O19 C21 C13 111.1(2) . . ?
C8 N1AA C2 128.99(15) . . ?
C3AA N1AA C2 123.51(15) . . ?
C3AA N1AA C8 107.41(15) . . ?
C8 C2AA H2AA 127.0 . . ?
C8 C2AA C3AA 105.95(16) . 2_567 ?
C3AA C2AA H2AA 127.0 2_567 . ?
N1AA C8 C15 123.74(16) . . ?
C2AA C8 C15 126.61(17) . . ?
C2AA C8 N1AA 109.26(16) . . ?
N1AA C3AA C2AA 142.62(17) . 2_567 ?
C3AA C3AA N1AA 108.0(2) 2_567 . ?
C3AA C3AA C2AA 109.4(2) 2_567 2_567 ?
F4AA C3 C7 113.7(2) . . ?
F4AA C3 F1 104.3(2) . . ?
F4AA C3 F2 108.0(2) . . ?
F1 C3 C7 112.6(2) . . ?
F2 C3 C7 112.5(2) . . ?
F2 C3 F1 105.0(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C0AA C1 H1A 109.5 . . ?
C0AA C1 H1B 109.5 . . ?
C0AA C1 H1C 109.5 . . ?
O19 C0AA H0AA 110.1 . . ?
O19 C0AA H0AB 110.1 . . ?
C1 C0AA O19 108.2(3) . . ?
C1 C0AA H0AA 110.1 . . ?
C1 C0AA H0AB 110.1 . . ?
H0AA C0AA H0AB 108.4 . . ?

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
C2 C5 C20 C13 0.0(3) . . . . ?
C2 C11 C14 C13 0.3(3) . . . . ?
C2 N1AA C8 C15 10.4(3) . . . . ?
C2 N1AA C8 C2AA -176.34(17) . . . . ?
C2 N1AA C3AA C2AA -2.6(4) . . . 2_567 ?
C2 N1AA C3AA C3AA 176.18(18) . . . 2_567 ?
C5 C2 C11 C14 -0.9(3) . . . . ?
C5 C2 N1AA C8 56.4(3) . . . . ?
C5 C2 N1AA C3AA -119.7(2) . . . . ?
C6 C15 C8 N1AA -150.75(18) . . . . ?
C6 C15 C8 C2AA 37.1(3) . . . . ?
C9 C15 C8 N1AA 33.9(3) . . . . ?
C9 C15 C8 C2AA -138.3(2) . . . . ?
C11 C2 C5 C20 0.7(3) . . . . ?
C11 C2 N1AA C8 -124.7(2) . . . . ?
C11 C2 N1AA C3AA 59.2(2) . . . . ?
C12 C7 C16 C6 -1.8(3) . . . . ?
C12 C7 C3 F4AA 163.8(2) . . . . ?
C12 C7 C3 F1 -77.9(3) . . . . ?
C12 C7 C3 F2 40.6(3) . . . . ?
C12 C9 C15 C6 -2.1(3) . . . . ?
C12 C9 C15 C8 173.34(19) . . . . ?
C14 C13 C20 C5 -0.6(3) . . . . ?
C14 C13 C21 O17 -172.2(2) . . . . ?
C14 C13 C21 O19 9.1(3) . . . . ?
C15 C6 C16 C7 1.2(3) . . . . ?
C15 C9 C12 C7 1.6(3) . . . . ?
C16 C6 C15 C9 0.7(3) . . . . ?
C16 C6 C15 C8 -174.89(17) . . . . ?
C16 C7 C12 C9 0.3(3) . . . . ?
C16 C7 C3 F4AA -16.0(3) . . . . ?
C16 C7 C3 F1 102.3(3) . . . . ?
C16 C7 C3 F2 -139.2(3) . . . . ?
C20 C13 C14 C11 0.5(3) . . . . ?
C20 C13 C21 O17 8.6(3) . . . . ?
C20 C13 C21 O19 -170.12(19) . . . . ?
C21 C13 C14 C11 -178.72(18) . . . . ?
C21 C13 C20 C5 178.59(18) . . . . ?
C21 O19 C0AA C1 -153.3(5) . . . . ?
N1AA C2 C5 C20 179.62(16) . . . . ?
N1AA C2 C11 C14 -179.80(17) . . . . ?
C8 N1AA C3AA C2AA -179.4(2) . . . 2_567 ?
C8 N1AA C3AA C3AA -0.6(2) . . . 2_567 ?
C3AA N1AA C8 C15 -173.12(17) . . . . ?
C3AA N1AA C8 C2AA 0.2(2) . . . . ?
C3AA C2AA C8 C15 173.33(18) 2_567 . . . ?
C3AA C2AA C8 N1AA 0.3(2) 2_567 . . . ?
C3 C7 C12 C9 -179.5(2) . . . . ?
C3 C7 C16 C6 178.03(19) . . . . ?
C0AA O19 C21 C13 176.9(2) . . . . ?
C0AA O19 C21 O17 -1.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.229
_oxdiff_exptl_absorpt_empirical_full_min 0.785
