# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1836413'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25.33 H29.33 F4 N1.33 O4 S1.33'
_chemical_formula_weight         535.25

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'
S S 0.3331 0.5567 '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                   9.13630(10)
_cell_length_b                   13.54900(10)
_cell_length_c                   15.3864(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1904.65(4)
_cell_formula_units_Z            3
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    5696
_cell_measurement_theta_min      4.3310
_cell_measurement_theta_max      70.8820

_exptl_crystal_description       block
_exptl_crystal_colour            'colorless crystal'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    1.947
_shelx_estimated_absorpt_T_min   0.575
_shelx_estimated_absorpt_T_max   0.674
_exptl_absorpt_correction_T_min  0.60269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            7202
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.348
_diffrn_reflns_theta_max         71.335
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3481
_reflns_number_gt                3361
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.999

_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 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0820P)²+0.2970P] 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
_refine_ls_extinction_coef       0.0053(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3481
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0442
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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
S1 S 0.77729(10) 0.75232(6) 0.66856(5) 0.0552(3) Uani 1 1 d . . . . .
N1 N 0.7034(3) 0.37936(15) 0.71780(15) 0.0370(5) Uani 1 1 d . . . . .
C7 C 0.6005(3) 0.31532(19) 0.55446(18) 0.0350(6) Uani 1 1 d . . . . .
C10 C 0.5055(3) 0.4807(2) 0.5320(2) 0.0483(7) Uani 1 1 d . . . . .
H10 H 0.4731 0.5406 0.5544 0.058 Uiso 1 1 calc R U . . .
C6 C 0.6391(3) 0.23993(19) 0.62057(17) 0.0345(5) Uani 1 1 d . . . . .
C9 C 0.5626(3) 0.4230(2) 0.6825(2) 0.0406(6) Uani 1 1 d . . . . .
H9A H 0.4794 0.3924 0.7109 0.049 Uiso 1 1 calc R U . . .
H9B H 0.5597 0.4932 0.6946 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5534(3) 0.4064(2) 0.58693(19) 0.0375(6) Uani 1 1 d . . . . .
C5 C 0.6139(3) 0.1378(2) 0.6115(2) 0.0401(6) Uani 1 1 d . . . . .
C1 C 0.7004(3) 0.27050(17) 0.69984(17) 0.0345(5) Uani 1 1 d . . . . .
O3 O 0.6539(4) 0.8135(3) 0.6740(3) 0.0991(12) Uani 1 1 d . . . . .
C3 C 0.7448(3) 0.1049(2) 0.7461(2) 0.0449(7) Uani 1 1 d . . . . .
C2 C 0.7559(3) 0.2060(2) 0.76079(19) 0.0420(6) Uani 1 1 d . . . . .
H2 H 0.8002 0.2297 0.8111 0.050 Uiso 1 1 calc R U . . .
C11 C 0.5066(4) 0.4645(3) 0.4427(2) 0.0558(8) Uani 1 1 d . . . . .
H11 H 0.4674 0.5115 0.4053 0.067 Uiso 1 1 calc R U . . .
C4 C 0.6706(3) 0.0732(2) 0.6736(2) 0.0452(6) Uani 1 1 d . . . . .
H4 H 0.6577 0.0058 0.6655 0.054 Uiso 1 1 calc R U . . .
F2 F 0.6852(5) 0.6848(4) 0.5208(2) 0.1423(18) Uani 1 1 d . . . . .
O1 O 0.7622(7) 0.6575(2) 0.7050(2) 0.1173(17) Uani 1 1 d . . . . .
C13 C 0.6197(3) 0.3044(2) 0.46451(19) 0.0407(6) Uani 1 1 d . . . . .
O2 O 0.9100(4) 0.8041(4) 0.6891(3) 0.1142(14) Uani 1 1 d . . . . .
C15 C 0.7079(4) 0.2231(3) 0.4224(2) 0.0520(7) Uani 1 1 d . . . . .
H15A H 0.7561 0.1850 0.4666 0.078 Uiso 1 1 calc R U . . .
H15B H 0.7798 0.2515 0.3844 0.078 Uiso 1 1 calc R U . . .
H15C H 0.6439 0.1811 0.3896 0.078 Uiso 1 1 calc R U . . .
C12 C 0.5654(4) 0.3793(3) 0.4099(2) 0.0524(8) Uani 1 1 d . . . . .
H12 H 0.5695 0.3707 0.3500 0.063 Uiso 1 1 calc R U . . .
C17 C 0.8363(3) 0.4244(2) 0.6771(3) 0.0512(7) Uani 1 1 d . . . . .
H17A H 0.8334 0.4142 0.6153 0.077 Uiso 1 1 calc R U . . .
H17B H 0.9226 0.3940 0.7005 0.077 Uiso 1 1 calc R U . . .
H17C H 0.8382 0.4939 0.6892 0.077 Uiso 1 1 calc R U . . .
C14 C 0.5190(4) 0.0948(3) 0.5411(2) 0.0577(9) Uani 1 1 d . . . . .
H14A H 0.4801 0.1471 0.5058 0.087 Uiso 1 1 calc R U . . .
H14B H 0.4399 0.0586 0.5670 0.087 Uiso 1 1 calc R U . . .
H14C H 0.5763 0.0513 0.5055 0.087 Uiso 1 1 calc R U . . .
C16 C 0.7069(5) 0.4017(3) 0.8136(2) 0.0595(8) Uani 1 1 d . . . . .
H16A H 0.6986 0.4716 0.8223 0.089 Uiso 1 1 calc R U . . .
H16B H 0.7976 0.3787 0.8378 0.089 Uiso 1 1 calc R U . . .
H16C H 0.6268 0.3689 0.8418 0.089 Uiso 1 1 calc R U . . .
C18 C 0.8111(4) 0.0337(3) 0.8100(3) 0.0620(9) Uani 1 1 d . . . . .
H18A H 0.9081 0.0552 0.8249 0.093 Uiso 1 1 calc R U . . .
H18B H 0.8157 -0.0308 0.7844 0.093 Uiso 1 1 calc R U . . .
H18C H 0.7519 0.0314 0.8615 0.093 Uiso 1 1 calc R U . . .
F3 F 0.8179(7) 0.8066(3) 0.5087(2) 0.157(2) Uani 1 1 d . . . . .
F1 F 0.9100(7) 0.6679(5) 0.5394(3) 0.176(3) Uani 1 1 d . . . . .
C19 C 0.7971(6) 0.7293(4) 0.5543(3) 0.0786(13) 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
S1 O3 1.402(3) . ?
S1 O1 1.409(3) . ?
S1 O2 1.436(4) . ?
S1 C19 1.795(4) . ?
N1 C17 1.497(4) . ?
N1 C1 1.501(3) . ?
N1 C16 1.505(4) . ?
N1 C9 1.517(4) . ?
C7 C8 1.399(4) . ?
C7 C13 1.403(4) . ?
C7 C6 1.484(4) . ?
C10 C8 1.386(4) . ?
C10 C11 1.390(5) . ?
C10 H10 0.9300 . ?
C6 C1 1.405(4) . ?
C6 C5 1.409(4) . ?
C9 C8 1.489(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C5 C4 1.395(4) . ?
C5 C14 1.505(4) . ?
C1 C2 1.379(4) . ?
C3 C4 1.375(5) . ?
C3 C2 1.392(4) . ?
C3 C18 1.505(4) . ?
C2 H2 0.9300 . ?
C11 C12 1.370(5) . ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
F2 C19 1.294(6) . ?
C13 C12 1.407(4) . ?
C13 C15 1.511(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C12 H12 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
F3 C19 1.275(6) . ?
F1 C19 1.345(7) . ?

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
O3 S1 O1 115.9(3) . . ?
O3 S1 O2 112.2(3) . . ?
O1 S1 O2 116.1(3) . . ?
O3 S1 C19 104.0(3) . . ?
O1 S1 C19 104.0(2) . . ?
O2 S1 C19 102.4(3) . . ?
C17 N1 C1 109.8(2) . . ?
C17 N1 C16 108.1(3) . . ?
C1 N1 C16 112.2(2) . . ?
C17 N1 C9 112.3(2) . . ?
C1 N1 C9 107.5(2) . . ?
C16 N1 C9 106.9(2) . . ?
C8 C7 C13 118.9(3) . . ?
C8 C7 C6 115.8(3) . . ?
C13 C7 C6 125.0(3) . . ?
C8 C10 C11 119.0(3) . . ?
C8 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C1 C6 C5 116.2(2) . . ?
C1 C6 C7 119.1(2) . . ?
C5 C6 C7 124.6(2) . . ?
C8 C9 N1 110.0(2) . . ?
C8 C9 H9A 109.7 . . ?
N1 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
N1 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C10 C8 C7 121.3(3) . . ?
C10 C8 C9 120.7(3) . . ?
C7 C8 C9 117.9(3) . . ?
C4 C5 C6 119.1(3) . . ?
C4 C5 C14 117.6(3) . . ?
C6 C5 C14 123.1(3) . . ?
C2 C1 C6 123.4(2) . . ?
C2 C1 N1 119.4(2) . . ?
C6 C1 N1 117.2(2) . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 C18 121.9(3) . . ?
C2 C3 C18 119.7(3) . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C3 C4 C5 122.9(3) . . ?
C3 C4 H4 118.6 . . ?
C5 C4 H4 118.6 . . ?
C7 C13 C12 117.9(3) . . ?
C7 C13 C15 124.5(3) . . ?
C12 C13 C15 117.3(3) . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 C13 121.7(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F3 C19 F2 106.4(5) . . ?
F3 C19 F1 107.5(5) . . ?
F2 C19 F1 104.5(5) . . ?
F3 C19 S1 114.3(4) . . ?
F2 C19 S1 113.0(4) . . ?
F1 C19 S1 110.5(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
C8 C7 C6 C1 -33.0(3) . . . . ?
C13 C7 C6 C1 141.3(3) . . . . ?
C8 C7 C6 C5 144.6(3) . . . . ?
C13 C7 C6 C5 -41.1(4) . . . . ?
C17 N1 C9 C8 59.9(3) . . . . ?
C1 N1 C9 C8 -61.0(3) . . . . ?
C16 N1 C9 C8 178.3(2) . . . . ?
C11 C10 C8 C7 -1.0(5) . . . . ?
C11 C10 C8 C9 176.2(3) . . . . ?
C13 C7 C8 C10 9.4(4) . . . . ?
C6 C7 C8 C10 -175.9(3) . . . . ?
C13 C7 C8 C9 -167.9(3) . . . . ?
C6 C7 C8 C9 6.8(4) . . . . ?
N1 C9 C8 C10 -137.4(3) . . . . ?
N1 C9 C8 C7 39.9(3) . . . . ?
C1 C6 C5 C4 -9.9(4) . . . . ?
C7 C6 C5 C4 172.5(3) . . . . ?
C1 C6 C5 C14 165.5(3) . . . . ?
C7 C6 C5 C14 -12.1(4) . . . . ?
C5 C6 C1 C2 10.3(4) . . . . ?
C7 C6 C1 C2 -171.9(2) . . . . ?
C5 C6 C1 N1 -169.3(2) . . . . ?
C7 C6 C1 N1 8.5(4) . . . . ?
C17 N1 C1 C2 95.5(3) . . . . ?
C16 N1 C1 C2 -24.7(4) . . . . ?
C9 N1 C1 C2 -142.0(3) . . . . ?
C17 N1 C1 C6 -84.9(3) . . . . ?
C16 N1 C1 C6 154.8(3) . . . . ?
C9 N1 C1 C6 37.5(3) . . . . ?
C6 C1 C2 C3 -3.4(4) . . . . ?
N1 C1 C2 C3 176.1(2) . . . . ?
C4 C3 C2 C1 -3.9(4) . . . . ?
C18 C3 C2 C1 177.1(3) . . . . ?
C8 C10 C11 C12 -5.2(5) . . . . ?
C2 C3 C4 C5 4.0(4) . . . . ?
C18 C3 C4 C5 -177.0(3) . . . . ?
C6 C5 C4 C3 3.1(4) . . . . ?
C14 C5 C4 C3 -172.5(3) . . . . ?
C8 C7 C13 C12 -11.4(4) . . . . ?
C6 C7 C13 C12 174.4(3) . . . . ?
C8 C7 C13 C15 162.1(3) . . . . ?
C6 C7 C13 C15 -12.1(4) . . . . ?
C10 C11 C12 C13 2.9(5) . . . . ?
C7 C13 C12 C11 5.5(5) . . . . ?
C15 C13 C12 C11 -168.5(3) . . . . ?
O3 S1 C19 F3 60.8(5) . . . . ?
O1 S1 C19 F3 -177.5(5) . . . . ?
O2 S1 C19 F3 -56.2(6) . . . . ?
O3 S1 C19 F2 -61.1(5) . . . . ?
O1 S1 C19 F2 60.6(5) . . . . ?
O2 S1 C19 F2 -178.1(5) . . . . ?
O3 S1 C19 F1 -177.9(4) . . . . ?
O1 S1 C19 F1 -56.1(5) . . . . ?
O2 S1 C19 F1 65.2(5) . . . . ?

_refine_diff_density_max         0.280
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.045

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1836417'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N O2'
_chemical_formula_weight         347.44

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'

_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                   8.5712(3)
_cell_length_b                   9.5542(3)
_cell_length_c                   12.0362(4)
_cell_angle_alpha                91.908(3)
_cell_angle_beta                 103.104(3)
_cell_angle_gamma                97.556(3)
_cell_volume                     949.62(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4248
_cell_measurement_theta_min      4.6570
_cell_measurement_theta_max      71.2280

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.603
_shelx_estimated_absorpt_T_min   0.874
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_T_min  0.88317
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2169
_diffrn_reflns_number            5916
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_av_R_equivalents  0.0134
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.779
_diffrn_reflns_theta_max         71.284
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3554
_reflns_number_gt                3258
_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 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0679P)²+0.1867P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3554
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O2 O 0.74778(11) 0.25693(10) 0.42452(9) 0.0481(3) Uani 1 1 d . . . . .
O1 O 0.72801(12) 0.48847(10) 0.42926(10) 0.0554(3) Uani 1 1 d . . . . .
N1 N 0.42468(12) 0.18463(11) 0.41586(9) 0.0359(2) Uani 1 1 d . . . . .
C1 C 0.25916(14) 0.22172(12) 0.24270(10) 0.0340(3) Uani 1 1 d . . . . .
C6 C 0.27536(14) 0.14293(12) 0.33915(10) 0.0338(3) Uani 1 1 d . . . . .
C8 C 0.40939(14) 0.33180(12) 0.25459(10) 0.0326(3) Uani 1 1 d . . . . .
C7 C 0.48408(14) 0.32593(12) 0.38708(10) 0.0333(3) Uani 1 1 d . . . . .
H7 H 0.4381 0.3945 0.4279 0.040 Uiso 1 1 calc R U . . .
C22 C 0.66600(15) 0.36697(13) 0.41678(11) 0.0378(3) Uani 1 1 d . . . . .
C9 C 0.37089(15) 0.48092(13) 0.23048(11) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.12490(16) 0.19002(14) 0.15179(11) 0.0417(3) Uani 1 1 d . . . . .
C5 C 0.15430(16) 0.03604(13) 0.35023(12) 0.0401(3) Uani 1 1 d . . . . .
H5 H 0.1656 -0.0153 0.4152 0.048 Uiso 1 1 calc R U . . .
C17 C 0.52182(16) 0.28477(14) 0.18277(11) 0.0394(3) Uani 1 1 d . . . . .
C14 C 0.46815(17) 0.57599(14) 0.18063(11) 0.0422(3) Uani 1 1 d . . . . .
C10 C 0.23631(18) 0.52511(15) 0.26023(13) 0.0480(3) Uani 1 1 d . . . . .
H10 H 0.1719 0.4635 0.2951 0.058 Uiso 1 1 calc R U . . .
C4 C 0.01566(16) 0.00743(13) 0.26192(13) 0.0433(3) Uani 1 1 d . . . . .
C3 C 0.00352(16) 0.08213(15) 0.16445(13) 0.0462(3) Uani 1 1 d . . . . .
H3 H -0.0884 0.0600 0.1052 0.055 Uiso 1 1 calc R U . . .
C16 C 0.61746(18) 0.37974(16) 0.14106(13) 0.0489(3) Uani 1 1 d . . . . .
H16 H 0.6904 0.3464 0.1037 0.059 Uiso 1 1 calc R U . . .
C21 C 0.43862(19) 0.16713(17) 0.53728(12) 0.0505(4) Uani 1 1 d . . . . .
H21A H 0.3701 0.2247 0.5651 0.076 Uiso 1 1 calc R U . . .
H21B H 0.5489 0.1955 0.5781 0.076 Uiso 1 1 calc R U . . .
H21C H 0.4061 0.0696 0.5487 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4255(2) 0.71061(15) 0.15972(13) 0.0542(4) Uani 1 1 d . . . . .
H13 H 0.4900 0.7739 0.1260 0.065 Uiso 1 1 calc R U . . .
C20 C 0.5273(2) 0.12891(16) 0.16687(15) 0.0551(4) Uani 1 1 d . . . . .
H20A H 0.5466 0.0890 0.2400 0.083 Uiso 1 1 calc R U . . .
H20B H 0.6130 0.1146 0.1302 0.083 Uiso 1 1 calc R U . . .
H20C H 0.4260 0.0836 0.1202 0.083 Uiso 1 1 calc R U . . .
C15 C 0.61654(19) 0.53524(16) 0.14969(14) 0.0543(4) Uani 1 1 d . . . . .
H15A H 0.6247 0.5728 0.0770 0.065 Uiso 1 1 calc R U . . .
H15B H 0.7111 0.5784 0.2069 0.065 Uiso 1 1 calc R U . . .
C12 C 0.2913(2) 0.75165(16) 0.18762(14) 0.0589(4) Uani 1 1 d . . . . .
H12 H 0.2643 0.8413 0.1721 0.071 Uiso 1 1 calc R U . . .
C11 C 0.1968(2) 0.65894(17) 0.23880(15) 0.0587(4) Uani 1 1 d . . . . .
H11 H 0.1063 0.6863 0.2590 0.070 Uiso 1 1 calc R U . . .
C18 C 0.1067(2) 0.26670(19) 0.04385(14) 0.0639(5) Uani 1 1 d . . . . .
H18A H 0.0717 0.3562 0.0560 0.096 Uiso 1 1 calc R U . . .
H18B H 0.0279 0.2110 -0.0163 0.096 Uiso 1 1 calc R U . . .
H18C H 0.2089 0.2820 0.0228 0.096 Uiso 1 1 calc R U . . .
C19 C -0.12311(19) -0.10192(17) 0.27362(17) 0.0610(4) Uani 1 1 d . . . . .
H19A H -0.0851 -0.1631 0.3324 0.092 Uiso 1 1 calc R U . . .
H19B H -0.1658 -0.1569 0.2024 0.092 Uiso 1 1 calc R U . . .
H19C H -0.2066 -0.0553 0.2935 0.092 Uiso 1 1 calc R U . . .
C23 C 0.92047(19) 0.2931(2) 0.44038(19) 0.0701(5) Uani 1 1 d . . . . .
H23A H 0.9433 0.3445 0.3774 0.105 Uiso 1 1 calc R U . . .
H23B H 0.9696 0.2081 0.4440 0.105 Uiso 1 1 calc R U . . .
H23C H 0.9635 0.3506 0.5103 0.105 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
O2 C22 1.3327(16) . ?
O2 C23 1.4421(18) . ?
O1 C22 1.2010(16) . ?
N1 C6 1.3982(16) . ?
N1 C21 1.4563(17) . ?
N1 C7 1.4601(15) . ?
C1 C2 1.3887(18) . ?
C1 C6 1.3950(17) . ?
C1 C8 1.5280(16) . ?
C6 C5 1.3895(17) . ?
C8 C9 1.5267(17) . ?
C8 C17 1.5308(17) . ?
C8 C7 1.5838(16) . ?
C7 C22 1.5132(17) . ?
C7 H7 0.9800 . ?
C9 C10 1.3938(19) . ?
C9 C14 1.3942(19) . ?
C2 C3 1.4030(19) . ?
C2 C18 1.500(2) . ?
C5 C4 1.393(2) . ?
C5 H5 0.9300 . ?
C17 C16 1.3299(19) . ?
C17 C20 1.5033(19) . ?
C14 C13 1.398(2) . ?
C14 C15 1.498(2) . ?
C10 C11 1.383(2) . ?
C10 H10 0.9300 . ?
C4 C3 1.384(2) . ?
C4 C19 1.5116(18) . ?
C3 H3 0.9300 . ?
C16 C15 1.487(2) . ?
C16 H16 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C13 C12 1.369(3) . ?
C13 H13 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C12 C11 1.376(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C22 O2 C23 114.89(12) . . ?
C6 N1 C21 119.23(11) . . ?
C6 N1 C7 106.30(9) . . ?
C21 N1 C7 115.28(10) . . ?
C2 C1 C6 120.69(11) . . ?
C2 C1 C8 129.51(11) . . ?
C6 C1 C8 109.71(10) . . ?
C5 C6 C1 121.31(12) . . ?
C5 C6 N1 127.30(12) . . ?
C1 C6 N1 111.37(10) . . ?
C9 C8 C1 113.63(10) . . ?
C9 C8 C17 111.90(10) . . ?
C1 C8 C17 111.07(10) . . ?
C9 C8 C7 109.10(9) . . ?
C1 C8 C7 98.86(9) . . ?
C17 C8 C7 111.59(10) . . ?
N1 C7 C22 115.92(10) . . ?
N1 C7 C8 105.50(9) . . ?
C22 C7 C8 111.78(10) . . ?
N1 C7 H7 107.8 . . ?
C22 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
O1 C22 O2 124.25(12) . . ?
O1 C22 C7 121.89(12) . . ?
O2 C22 C7 113.84(10) . . ?
C10 C9 C14 118.54(12) . . ?
C10 C9 C8 119.59(11) . . ?
C14 C9 C8 121.86(12) . . ?
C1 C2 C3 117.21(12) . . ?
C1 C2 C18 122.51(12) . . ?
C3 C2 C18 120.28(12) . . ?
C6 C5 C4 118.54(12) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C16 C17 C20 121.33(13) . . ?
C16 C17 C8 120.67(12) . . ?
C20 C17 C8 117.90(11) . . ?
C9 C14 C13 119.12(14) . . ?
C9 C14 C15 120.75(12) . . ?
C13 C14 C15 120.13(13) . . ?
C11 C10 C9 121.21(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C3 C4 C5 119.76(12) . . ?
C3 C4 C19 120.02(14) . . ?
C5 C4 C19 120.20(14) . . ?
C4 C3 C2 122.36(13) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C17 C16 C15 124.91(13) . . ?
C17 C16 H16 117.5 . . ?
C15 C16 H16 117.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C13 C14 121.65(15) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C15 C14 113.46(12) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C13 C12 C11 119.34(14) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C11 C10 120.11(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C19 H19A 109.5 . . ?
C4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C2 C1 C6 C5 -3.68(19) . . . . ?
C8 C1 C6 C5 179.51(11) . . . . ?
C2 C1 C6 N1 175.06(11) . . . . ?
C8 C1 C6 N1 -1.76(14) . . . . ?
C21 N1 C6 C5 -29.33(18) . . . . ?
C7 N1 C6 C5 -161.67(12) . . . . ?
C21 N1 C6 C1 152.03(12) . . . . ?
C7 N1 C6 C1 19.69(13) . . . . ?
C2 C1 C8 C9 53.08(17) . . . . ?
C6 C1 C8 C9 -130.47(11) . . . . ?
C2 C1 C8 C17 -74.15(17) . . . . ?
C6 C1 C8 C17 102.30(12) . . . . ?
C2 C1 C8 C7 168.52(13) . . . . ?
C6 C1 C8 C7 -15.03(12) . . . . ?
C6 N1 C7 C22 -153.03(10) . . . . ?
C21 N1 C7 C22 72.48(14) . . . . ?
C6 N1 C7 C8 -28.78(12) . . . . ?
C21 N1 C7 C8 -163.26(10) . . . . ?
C9 C8 C7 N1 144.92(10) . . . . ?
C1 C8 C7 N1 26.02(11) . . . . ?
C17 C8 C7 N1 -90.91(11) . . . . ?
C9 C8 C7 C22 -88.25(12) . . . . ?
C1 C8 C7 C22 152.85(10) . . . . ?
C17 C8 C7 C22 35.91(13) . . . . ?
C23 O2 C22 O1 -4.8(2) . . . . ?
C23 O2 C22 C7 173.55(13) . . . . ?
N1 C7 C22 O1 -157.77(12) . . . . ?
C8 C7 C22 O1 81.29(15) . . . . ?
N1 C7 C22 O2 23.81(15) . . . . ?
C8 C7 C22 O2 -97.13(12) . . . . ?
C1 C8 C9 C10 34.08(16) . . . . ?
C17 C8 C9 C10 160.87(12) . . . . ?
C7 C8 C9 C10 -75.15(14) . . . . ?
C1 C8 C9 C14 -146.84(12) . . . . ?
C17 C8 C9 C14 -20.05(16) . . . . ?
C7 C8 C9 C14 103.93(13) . . . . ?
C6 C1 C2 C3 3.74(19) . . . . ?
C8 C1 C2 C3 179.85(12) . . . . ?
C6 C1 C2 C18 -176.61(14) . . . . ?
C8 C1 C2 C18 -0.5(2) . . . . ?
C1 C6 C5 C4 0.70(19) . . . . ?
N1 C6 C5 C4 -177.81(12) . . . . ?
C9 C8 C17 C16 23.20(17) . . . . ?
C1 C8 C17 C16 151.36(13) . . . . ?
C7 C8 C17 C16 -99.37(15) . . . . ?
C9 C8 C17 C20 -160.23(12) . . . . ?
C1 C8 C17 C20 -32.07(16) . . . . ?
C7 C8 C17 C20 77.20(14) . . . . ?
C10 C9 C14 C13 -1.52(19) . . . . ?
C8 C9 C14 C13 179.39(12) . . . . ?
C10 C9 C14 C15 178.46(13) . . . . ?
C8 C9 C14 C15 -0.63(19) . . . . ?
C14 C9 C10 C11 1.5(2) . . . . ?
C8 C9 C10 C11 -179.42(13) . . . . ?
C6 C5 C4 C3 2.0(2) . . . . ?
C6 C5 C4 C19 -176.33(12) . . . . ?
C5 C4 C3 C2 -1.9(2) . . . . ?
C19 C4 C3 C2 176.48(13) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C18 C2 C3 C4 179.31(15) . . . . ?
C20 C17 C16 C15 178.04(15) . . . . ?
C8 C17 C16 C15 -5.5(2) . . . . ?
C9 C14 C13 C12 0.4(2) . . . . ?
C15 C14 C13 C12 -179.56(14) . . . . ?
C17 C16 C15 C14 -16.2(2) . . . . ?
C9 C14 C15 C16 18.9(2) . . . . ?
C13 C14 C15 C16 -161.16(13) . . . . ?
C14 C13 C12 C11 0.8(2) . . . . ?
C13 C12 C11 C10 -0.9(2) . . . . ?
C9 C10 C11 C12 -0.3(2) . . . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.046

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_1153
_database_code_depnum_ccdc_archive 'CCDC 1836416'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-06-14 downloaded from the CCDC.
;
_audit_creation_date             2018-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C F3 O3 S, C16 H18 N'
_chemical_formula_sum            'C17 H18 F3 N O3 S'
_chemical_formula_weight         373.38
_chemical_absolute_configuration ad
_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'
F F 0.0171 0.0103 '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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   8.0524(6)
_cell_length_b                   10.2790(6)
_cell_length_c                   21.1646(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1751.80(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6241
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      28.3550
_cell_measurement_theta_min      2.6860
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.231
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            18781
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.582
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -37.00  65.00   1.00    3.50    --  -11.59  19.00  60.00  102
  2  ω     54.00  86.00   1.00    3.50    --   11.74  37.00-120.00   32
  3  ω    -64.00  -7.00   1.00    3.50    --   11.74 -77.00 120.00   57
  4  ω    -44.00 -16.00   1.00    3.50    --  -11.59  77.00   0.00   28
  5  ω    -36.00 -10.00   1.00    3.50    --  -11.59  77.00  60.00   26
  6  ω      0.00  58.00   1.00    3.50    --   11.74  77.00 -90.00   58
  7  ω    -18.00  78.00   1.00    3.50    --   11.74  77.00 150.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0794114000
_diffrn_orient_matrix_UB_12      -0.0211665000
_diffrn_orient_matrix_UB_13      0.0102561000
_diffrn_orient_matrix_UB_21      -0.0379647000
_diffrn_orient_matrix_UB_22      -0.0391553000
_diffrn_orient_matrix_UB_23      0.0235048000
_diffrn_orient_matrix_UB_31      -0.0037079000
_diffrn_orient_matrix_UB_32      -0.0527612000
_diffrn_orient_matrix_UB_33      -0.0215502000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.699
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                3757
_reflns_number_total             4423
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.335
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1268 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.044
_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)+(0.0361P)²+0.4961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0982
_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:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4), C10(H10), C2(H2), C11(H11), C12(H12), C3(H3)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C15(H15A,H15B,H15C), C14(H14A,H14B,H14C)
;
_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
S1 S 0.71226(9) 0.25705(7) 0.23558(3) 0.01982(17) Uani 1 1 d . . . . .
F3 F 0.6046(3) 0.05346(19) 0.29732(10) 0.0428(6) Uani 1 1 d . . . . .
F1 F 0.7003(3) 0.2062(2) 0.35634(8) 0.0418(5) Uani 1 1 d . . . . .
F2 F 0.8680(3) 0.0834(2) 0.30462(11) 0.0494(6) Uani 1 1 d . . . . .
O2 O 0.8438(3) 0.3477(2) 0.24878(10) 0.0273(5) Uani 1 1 d . . . . .
O1 O 0.7392(3) 0.1746(2) 0.18131(10) 0.0270(5) Uani 1 1 d . . . . .
O3 O 0.5469(3) 0.3090(2) 0.23995(10) 0.0278(5) Uani 1 1 d . . . . .
N1 N 0.7900(3) 0.6133(2) 0.36513(10) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.9235(4) 0.4548(3) 0.43775(14) 0.0196(6) Uani 1 1 d . . . . .
C6 C 0.8168(4) 0.6601(3) 0.47956(13) 0.0191(6) Uani 1 1 d . . . . .
C16 C 0.6302(4) 0.5369(3) 0.36211(14) 0.0244(7) Uani 1 1 d . . . . .
H16A H 0.636504 0.474696 0.328339 0.037 Uiso 1 1 calc GR . . . .
H16B H 0.539150 0.595134 0.354664 0.037 Uiso 1 1 calc GR . . . .
H16C H 0.613393 0.492092 0.401399 0.037 Uiso 1 1 calc GR . . . .
C9 C 0.9387(4) 0.5258(3) 0.37633(13) 0.0210(6) Uani 1 1 d . . . . .
H9A H 0.947353 0.463374 0.342105 0.025 Uiso 1 1 calc R . . . .
H9B H 1.039206 0.577825 0.376592 0.025 Uiso 1 1 calc R . . . .
C17 C 0.7227(5) 0.1434(3) 0.30171(15) 0.0299(7) Uani 1 1 d . . . . .
C7 C 0.8535(4) 0.5196(3) 0.48954(13) 0.0185(6) Uani 1 1 d . . . . .
C5 C 0.8218(4) 0.7522(3) 0.52824(13) 0.0225(6) Uani 1 1 d . . . . .
H5 H 0.847325 0.725195 0.569045 0.027 Uiso 1 1 calc R . . . .
C4 C 0.7896(4) 0.8826(3) 0.51708(14) 0.0248(7) Uani 1 1 d . . . . .
H4 H 0.796395 0.942120 0.550052 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8265(4) 0.4509(3) 0.54584(14) 0.0216(7) Uani 1 1 d . . . . .
C1 C 0.7827(4) 0.7077(3) 0.41862(12) 0.0192(6) Uani 1 1 d . . . . .
C10 C 0.9765(4) 0.3268(3) 0.44254(14) 0.0231(7) Uani 1 1 d . . . . .
H10 H 1.023376 0.285232 0.407828 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7473(4) 0.8373(3) 0.40733(14) 0.0249(7) Uani 1 1 d . . . . .
H2 H 0.723621 0.865612 0.366586 0.030 Uiso 1 1 calc R . . . .
C11 C 0.9593(4) 0.2618(3) 0.49894(15) 0.0257(7) Uani 1 1 d . . . . .
H11 H 0.999503 0.177420 0.503249 0.031 Uiso 1 1 calc R . . . .
C12 C 0.8817(4) 0.3226(3) 0.54929(14) 0.0263(7) Uani 1 1 d . . . . .
H12 H 0.865831 0.276440 0.586586 0.032 Uiso 1 1 calc R . . . .
C15 C 0.8156(4) 0.6768(3) 0.30159(14) 0.0296(8) Uani 1 1 d . . . . .
H15A H 0.832592 0.610989 0.270085 0.044 Uiso 1 1 calc GR . . . .
H15B H 0.911096 0.732610 0.303332 0.044 Uiso 1 1 calc GR . . . .
H15C H 0.719279 0.727345 0.290927 0.044 Uiso 1 1 calc GR . . . .
C3 C 0.7473(4) 0.9245(3) 0.45722(15) 0.0268(7) Uani 1 1 d . . . . .
H3 H 0.719010 1.011054 0.450413 0.032 Uiso 1 1 calc R . . . .
C14 C 0.7357(5) 0.5046(3) 0.60274(14) 0.0300(8) Uani 1 1 d . . . . .
H14A H 0.813369 0.547105 0.630238 0.045 Uiso 1 1 calc GR . . . .
H14B H 0.682555 0.434664 0.625022 0.045 Uiso 1 1 calc GR . . . .
H14C H 0.653380 0.566001 0.589043 0.045 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
S1 O2 1.438(2) . ?
S1 O1 1.444(2) . ?
S1 O3 1.438(2) . ?
S1 C17 1.825(3) . ?
F3 C17 1.330(4) . ?
F1 C17 1.337(4) . ?
F2 C17 1.323(4) . ?
N1 C16 1.509(4) . ?
N1 C9 1.516(4) . ?
N1 C1 1.492(3) . ?
N1 C15 1.509(4) . ?
C8 C9 1.496(4) . ?
C8 C7 1.401(4) . ?
C8 C10 1.387(4) . ?
C6 C7 1.489(4) . ?
C6 C5 1.400(4) . ?
C6 C1 1.407(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C7 C13 1.402(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.381(4) . ?
C13 C12 1.393(4) . ?
C13 C14 1.513(4) . ?
C1 C2 1.383(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 H12 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 S1 O1 115.09(13) . . ?
O2 S1 C17 103.40(14) . . ?
O1 S1 C17 103.15(13) . . ?
O3 S1 O2 115.40(13) . . ?
O3 S1 O1 114.11(14) . . ?
O3 S1 C17 103.38(15) . . ?
C16 N1 C9 111.8(2) . . ?
C1 N1 C16 109.7(2) . . ?
C1 N1 C9 107.4(2) . . ?
C1 N1 C15 113.6(2) . . ?
C15 N1 C16 107.7(2) . . ?
C15 N1 C9 106.8(2) . . ?
C7 C8 C9 118.8(3) . . ?
C10 C8 C9 120.1(3) . . ?
C10 C8 C7 121.2(3) . . ?
C5 C6 C7 123.1(3) . . ?
C5 C6 C1 116.4(3) . . ?
C1 C6 C7 120.4(2) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N1 C9 H9A 109.4 . . ?
N1 C9 H9B 109.4 . . ?
C8 C9 N1 111.1(2) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
F3 C17 S1 111.0(2) . . ?
F3 C17 F1 107.4(3) . . ?
F1 C17 S1 110.4(2) . . ?
F2 C17 S1 112.0(2) . . ?
F2 C17 F3 108.2(3) . . ?
F2 C17 F1 107.7(3) . . ?
C8 C7 C6 115.5(2) . . ?
C8 C7 C13 119.2(3) . . ?
C13 C7 C6 125.3(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C7 C13 C14 124.6(3) . . ?
C12 C13 C7 118.2(3) . . ?
C12 C13 C14 117.2(3) . . ?
C6 C1 N1 117.5(2) . . ?
C2 C1 N1 120.2(2) . . ?
C2 C1 C6 122.3(3) . . ?
C8 C10 H10 120.2 . . ?
C11 C10 C8 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.4(3) . . ?
C3 C2 H2 120.3 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C13 C12 H12 119.0 . . ?
C11 C12 C13 122.1(3) . . ?
C11 C12 H12 119.0 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
O2 S1 C17 F3 178.6(2) . . . . ?
O2 S1 C17 F1 59.5(3) . . . . ?
O2 S1 C17 F2 -60.4(3) . . . . ?
O1 S1 C17 F3 -61.2(3) . . . . ?
O1 S1 C17 F1 179.8(2) . . . . ?
O1 S1 C17 F2 59.8(2) . . . . ?
O3 S1 C17 F3 57.9(3) . . . . ?
O3 S1 C17 F1 -61.1(3) . . . . ?
O3 S1 C17 F2 178.9(2) . . . . ?
N1 C1 C2 C3 -177.5(3) . . . . ?
C8 C7 C13 C12 4.4(4) . . . . ?
C8 C7 C13 C14 -173.2(3) . . . . ?
C8 C10 C11 C12 3.3(5) . . . . ?
C6 C7 C13 C12 -174.2(3) . . . . ?
C6 C7 C13 C14 8.2(5) . . . . ?
C6 C5 C4 C3 1.6(5) . . . . ?
C6 C1 C2 C3 1.0(5) . . . . ?
C16 N1 C9 C8 -60.9(3) . . . . ?
C16 N1 C1 C6 80.9(3) . . . . ?
C16 N1 C1 C2 -100.5(3) . . . . ?
C9 N1 C1 C6 -40.7(3) . . . . ?
C9 N1 C1 C2 137.8(3) . . . . ?
C9 C8 C7 C6 -6.3(4) . . . . ?
C9 C8 C7 C13 175.0(3) . . . . ?
C9 C8 C10 C11 -178.9(3) . . . . ?
C7 C8 C9 N1 -37.2(4) . . . . ?
C7 C8 C10 C11 0.4(5) . . . . ?
C7 C6 C5 C4 178.9(3) . . . . ?
C7 C6 C1 N1 -1.8(4) . . . . ?
C7 C6 C1 C2 179.7(3) . . . . ?
C7 C13 C12 C11 -0.9(5) . . . . ?
C5 C6 C7 C8 -149.4(3) . . . . ?
C5 C6 C7 C13 29.3(5) . . . . ?
C5 C6 C1 N1 175.2(3) . . . . ?
C5 C6 C1 C2 -3.3(5) . . . . ?
C5 C4 C3 C2 -4.0(5) . . . . ?
C1 N1 C9 C8 59.4(3) . . . . ?
C1 C6 C7 C8 27.5(4) . . . . ?
C1 C6 C7 C13 -153.9(3) . . . . ?
C1 C6 C5 C4 2.0(4) . . . . ?
C1 C2 C3 C4 2.8(5) . . . . ?
C10 C8 C9 N1 142.1(3) . . . . ?
C10 C8 C7 C6 174.5(3) . . . . ?
C10 C8 C7 C13 -4.3(4) . . . . ?
C10 C11 C12 C13 -3.0(5) . . . . ?
C15 N1 C9 C8 -178.5(3) . . . . ?
C15 N1 C1 C6 -158.5(3) . . . . ?
C15 N1 C1 C2 20.0(4) . . . . ?
C14 C13 C12 C11 176.9(3) . . . . ?


_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.584
