# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_mo_cc114_1_0m
_database_code_depnum_ccdc_archive 'CCDC 1941564'
loop_
_audit_author_name
_audit_author_address
'Luciano Marchio'
;Universita degli studi di Parma
Italy
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-06 downloaded from the CCDC.
;
_audit_creation_date             2019-07-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3 S'
_chemical_formula_sum            'C20 H21 N O3 S'
_chemical_formula_weight         355.44
_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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.942(4)
_cell_length_b                   11.5163(11)
_cell_length_c                   9.4629(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.030(4)
_cell_angle_gamma                90
_cell_volume                     3653.1(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    485
_cell_measurement_temperature    270
_cell_measurement_theta_max      21.129
_cell_measurement_theta_min      2.800
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1808 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0991
_diffrn_reflns_av_unetI/netI     0.0607
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            19589
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.715
_diffrn_reflns_theta_min         2.944
_diffrn_ambient_temperature      270
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1950
_reflns_number_total             3460
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.186
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.00060(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3460
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.031
_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)+(0.0390P)²+2.7213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1309
_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 Ternary CH refined with riding coordinates:
 C2(H2), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C20(H20), C4(H4), C16(H16), C8(H8), C19(H19), C11(H11), C18(H18),
 C10(H10), C17(H17)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
S1 S 0.41686(2) 0.70380(7) 0.96427(8) 0.0531(3) Uani 1 1 d . . . . .
O2 O 0.43865(6) 0.60561(18) 1.0258(2) 0.0672(7) Uani 1 1 d . . . . .
O1 O 0.41682(7) 0.80931(18) 1.0441(2) 0.0644(6) Uani 1 1 d . . . . .
O3 O 0.26013(6) 0.42042(19) 0.8302(3) 0.0708(7) Uani 1 1 d . . . . .
N1 N 0.37000(7) 0.66344(19) 0.9282(2) 0.0480(6) Uani 1 1 d . . . . .
C2 C 0.32231(8) 0.5082(2) 0.8956(3) 0.0443(7) Uani 1 1 d . . . . .
H2 H 0.3263 0.4862 0.9968 0.053 Uiso 1 1 calc R . . . .
C6 C 0.43297(9) 0.7370(3) 0.8015(3) 0.0502(8) Uani 1 1 d . . . . .
C15 C 0.31691(9) 0.2909(2) 0.8460(3) 0.0466(7) Uani 1 1 d . . . . .
C14 C 0.30084(9) 0.4094(2) 0.8071(3) 0.0500(8) Uani 1 1 d . . . . .
H14 H 0.3021 0.4235 0.7057 0.060 Uiso 1 1 calc R . . . .
C1 C 0.36165(8) 0.5498(2) 0.8574(3) 0.0483(8) Uani 1 1 d . . . . .
H1A H 0.3827 0.4950 0.8911 0.058 Uiso 1 1 calc R . . . .
H1B H 0.3598 0.5578 0.7545 0.058 Uiso 1 1 calc R . . . .
C3 C 0.29120(9) 0.6015(3) 0.8708(3) 0.0542(8) Uani 1 1 d . . . . .
C7 C 0.43491(9) 0.8512(3) 0.7600(3) 0.0568(8) Uani 1 1 d . . . . .
H7 H 0.4277 0.9103 0.8178 0.068 Uiso 1 1 calc R . . . .
C20 C 0.30736(10) 0.2318(3) 0.9632(3) 0.0589(9) Uani 1 1 d . . . . .
H20 H 0.2889 0.2630 1.0158 0.071 Uiso 1 1 calc R . . . .
C4 C 0.29978(10) 0.7109(3) 0.8556(3) 0.0617(9) Uani 1 1 d . . . . .
H4 H 0.2790 0.7632 0.8308 0.074 Uiso 1 1 calc R . . . .
C5 C 0.34144(10) 0.7554(3) 0.8764(4) 0.0603(9) Uani 1 1 d . . . . .
H5A H 0.3474 0.7855 0.7864 0.072 Uiso 1 1 calc R . . . .
H5B H 0.3441 0.8187 0.9450 0.072 Uiso 1 1 calc R . . . .
C16 C 0.34385(10) 0.2420(3) 0.7695(4) 0.0622(9) Uani 1 1 d . . . . .
H16 H 0.3502 0.2808 0.6899 0.075 Uiso 1 1 calc R . . . .
C9 C 0.45838(9) 0.7922(3) 0.5445(4) 0.0633(9) Uani 1 1 d . . . . .
C8 C 0.44758(10) 0.8776(3) 0.6323(4) 0.0655(10) Uani 1 1 d . . . . .
H8 H 0.4488 0.9549 0.6049 0.079 Uiso 1 1 calc R . . . .
C19 C 0.32520(12) 0.1260(3) 1.0023(4) 0.0679(10) Uani 1 1 d . . . . .
H19 H 0.3188 0.0864 1.0812 0.081 Uiso 1 1 calc R . . . .
C11 C 0.44361(10) 0.6498(3) 0.7150(4) 0.0663(9) Uani 1 1 d . . . . .
H11 H 0.4426 0.5724 0.7425 0.080 Uiso 1 1 calc R . . . .
C18 C 0.35236(11) 0.0794(3) 0.9246(4) 0.0713(11) Uani 1 1 d . . . . .
H18 H 0.3645 0.0087 0.9515 0.086 Uiso 1 1 calc R . . . .
C10 C 0.45583(10) 0.6788(3) 0.5870(4) 0.0713(10) Uani 1 1 d . . . . .
H10 H 0.4625 0.6199 0.5279 0.086 Uiso 1 1 calc R . . . .
C17 C 0.36153(11) 0.1373(3) 0.8077(4) 0.0735(10) Uani 1 1 d . . . . .
H17 H 0.3797 0.1057 0.7543 0.088 Uiso 1 1 calc R . . . .
C13 C 0.25157(10) 0.5413(3) 0.8469(5) 0.0806(12) Uani 1 1 d . . . . .
H13A H 0.2378 0.5528 0.9281 0.097 Uiso 1 1 calc R . . . .
H13B H 0.2350 0.5710 0.7617 0.097 Uiso 1 1 calc R . . . .
C12 C 0.47283(11) 0.8200(4) 0.4046(4) 0.0925(13) Uani 1 1 d . . . . .
H12A H 0.4503 0.8295 0.3304 0.139 Uiso 1 1 calc GR . . . .
H12B H 0.4892 0.7576 0.3799 0.139 Uiso 1 1 calc GR . . . .
H12C H 0.4881 0.8905 0.4149 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
S1 O2 1.425(2) . ?
S1 O1 1.431(2) . ?
S1 N1 1.641(2) . ?
S1 C6 1.755(3) . ?
O3 C14 1.438(4) . ?
O3 C13 1.436(4) . ?
N1 C1 1.477(3) . ?
N1 C5 1.467(4) . ?
C2 H2 0.9800 . ?
C2 C14 1.528(4) . ?
C2 C1 1.515(4) . ?
C2 C3 1.499(4) . ?
C6 C7 1.377(4) . ?
C6 C11 1.379(4) . ?
C15 C14 1.494(4) . ?
C15 C20 1.383(4) . ?
C15 C16 1.373(4) . ?
C14 H14 0.9800 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C3 C4 1.306(4) . ?
C3 C13 1.499(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.384(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.488(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.369(5) . ?
C9 C8 1.373(5) . ?
C9 C10 1.373(5) . ?
C9 C12 1.517(5) . ?
C8 H8 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.375(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.382(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.369(5) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 120.10(13) . . ?
O2 S1 N1 106.52(12) . . ?
O2 S1 C6 108.55(15) . . ?
O1 S1 N1 105.61(13) . . ?
O1 S1 C6 107.74(14) . . ?
N1 S1 C6 107.73(13) . . ?
C13 O3 C14 108.5(2) . . ?
C1 N1 S1 117.13(19) . . ?
C5 N1 S1 115.65(19) . . ?
C5 N1 C1 114.7(2) . . ?
C14 C2 H2 108.9 . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C14 117.8(2) . . ?
C3 C2 H2 108.9 . . ?
C3 C2 C14 100.6(2) . . ?
C3 C2 C1 111.2(2) . . ?
C7 C6 S1 119.6(2) . . ?
C7 C6 C11 119.8(3) . . ?
C11 C6 S1 120.6(2) . . ?
C20 C15 C14 121.7(3) . . ?
C16 C15 C14 119.5(3) . . ?
C16 C15 C20 118.7(3) . . ?
O3 C14 C2 103.8(2) . . ?
O3 C14 C15 111.4(2) . . ?
O3 C14 H14 108.9 . . ?
C2 C14 H14 108.9 . . ?
C15 C14 C2 114.9(2) . . ?
C15 C14 H14 108.9 . . ?
N1 C1 C2 106.6(2) . . ?
N1 C1 H1A 110.4 . . ?
N1 C1 H1B 110.4 . . ?
C2 C1 H1A 110.4 . . ?
C2 C1 H1B 110.4 . . ?
H1A C1 H1B 108.6 . . ?
C4 C3 C2 123.0(3) . . ?
C4 C3 C13 129.8(3) . . ?
C13 C3 C2 106.6(2) . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C15 C20 H20 120.0 . . ?
C15 C20 C19 120.0(3) . . ?
C19 C20 H20 120.0 . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.8(3) . . ?
C5 C4 H4 118.6 . . ?
N1 C5 C4 111.1(2) . . ?
N1 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.5(3) . . ?
C17 C16 H16 119.2 . . ?
C8 C9 C12 122.0(4) . . ?
C10 C9 C8 118.0(3) . . ?
C10 C9 C12 120.0(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.5(3) . . ?
C9 C8 H8 119.3 . . ?
C20 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C18 C19 H19 119.9 . . ?
C6 C11 H11 120.4 . . ?
C6 C11 C10 119.1(3) . . ?
C10 C11 H11 120.4 . . ?
C19 C18 H18 120.1 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O3 C13 C3 105.9(3) . . ?
O3 C13 H13A 110.6 . . ?
O3 C13 H13B 110.6 . . ?
C3 C13 H13A 110.6 . . ?
C3 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?


_olex2_exptl_crystal_mounting_method cryoloop
_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_ccc365_36maest_0m
_database_code_depnum_ccdc_archive 'CCDC 1941565'
loop_
_audit_author_name
_audit_author_address
'Luciano Marchio'
;Universita degli studi di Parma
Italy
;
_audit_update_record             
;
2019-07-18 deposited with the CCDC.	2019-09-06 downloaded from the CCDC.
;
_audit_creation_date             2019-04-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O2'
_chemical_formula_sum            'C17 H16 O2'
_chemical_formula_weight         252.30
_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 0.0181 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'
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      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                   7.3872(2)
_cell_length_b                   10.8747(3)
_cell_length_c                   16.4977(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1325.32(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9193
_cell_measurement_temperature    200
_cell_measurement_theta_max      74.490
_cell_measurement_theta_min      4.065
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.648
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1569 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8366.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0084
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            40279
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.512
_diffrn_reflns_theta_min         5.363
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 Venture PhotonII'
_diffrn_measurement_method       'omega and phi scan'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus source'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                2675
_reflns_number_total             2682
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.293
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 1115 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.059
_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)+(0.0509P)²+0.1186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0835
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C16(H16), C17(H17), C11(H11), C14(H14), C12(H12), C13(H13), C5(H5)
;
_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
O1 O 0.26800(16) 0.17052(11) 0.60680(9) 0.0573(3) Uani 1 1 d . . . . .
O2 O 0.78418(18) 0.32699(12) 0.72976(8) 0.0583(3) Uani 1 1 d . . . . .
C9 C 0.3719(2) 0.43411(14) 0.48461(9) 0.0418(3) Uani 1 1 d . . . . .
H9 H 0.4778 0.4034 0.4590 0.050 Uiso 1 1 calc R . . . .
C16 C 0.0603(2) 0.52203(14) 0.56016(9) 0.0425(3) Uani 1 1 d . . . . .
H16 H -0.0462 0.5510 0.5862 0.051 Uiso 1 1 calc R . . . .
C17 C 0.14458(19) 0.41900(15) 0.58917(9) 0.0403(3) Uani 1 1 d . . . . .
H17 H 0.0970 0.3777 0.6352 0.048 Uiso 1 1 calc R . . . .
C8 C 0.30284(19) 0.37372(13) 0.55063(9) 0.0381(3) Uani 1 1 d . . . . .
C2 C 0.50329(19) 0.28619(13) 0.66249(9) 0.0368(3) Uani 1 1 d . . . . .
H2 H 0.4288 0.3376 0.7001 0.044 Uiso 1 1 calc R . . . .
C15 C 0.1286(2) 0.58616(14) 0.49228(9) 0.0410(3) Uani 1 1 d . . . . .
C10 C 0.2879(2) 0.54162(15) 0.45393(9) 0.0421(3) Uani 1 1 d . . . . .
C3 C 0.6902(2) 0.34053(16) 0.65472(10) 0.0473(4) Uani 1 1 d . . . . .
H3A H 0.7576 0.2980 0.6111 0.057 Uiso 1 1 calc R . . . .
H3B H 0.6813 0.4287 0.6404 0.057 Uiso 1 1 calc R . . . .
C11 C 0.3546(3) 0.60536(18) 0.38494(10) 0.0541(4) Uani 1 1 d . . . . .
H11 H 0.4610 0.5771 0.3585 0.065 Uiso 1 1 calc R . . . .
C6 C 0.5163(2) 0.15709(14) 0.69463(10) 0.0467(4) Uani 1 1 d . . . . .
C1 C 0.3985(2) 0.26277(14) 0.58433(9) 0.0402(3) Uani 1 1 d . . . . .
H1 H 0.4822 0.2286 0.5424 0.048 Uiso 1 1 calc R . . . .
C14 C 0.0430(3) 0.69290(16) 0.46098(11) 0.0523(4) Uani 1 1 d . . . . .
H14 H -0.0628 0.7237 0.4866 0.063 Uiso 1 1 calc R . . . .
C7 C 0.3524(3) 0.08621(15) 0.66136(12) 0.0545(4) Uani 1 1 d . . . . .
H7A H 0.3915 0.0109 0.6326 0.065 Uiso 1 1 calc R . . . .
H7B H 0.2687 0.0629 0.7057 0.065 Uiso 1 1 calc R . . . .
C12 C 0.2663(3) 0.70719(19) 0.35631(11) 0.0630(5) Uani 1 1 d . . . . .
H12 H 0.3113 0.7483 0.3097 0.076 Uiso 1 1 calc R . . . .
C13 C 0.1105(3) 0.75156(18) 0.39489(12) 0.0621(5) Uani 1 1 d . . . . .
H13 H 0.0518 0.8230 0.3747 0.075 Uiso 1 1 calc R . . . .
C5 C 0.6589(3) 0.11766(17) 0.73354(12) 0.0584(5) Uani 1 1 d . . . . .
H5 H 0.6653 0.0342 0.7502 0.070 Uiso 1 1 calc R . . . .
C4 C 0.8111(3) 0.2024(2) 0.75186(14) 0.0649(5) Uani 1 1 d . . . . .
H4A H 0.8355 0.1989 0.8108 0.078 Uiso 1 1 calc R . . . .
H4B H 0.9205 0.1718 0.7237 0.078 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
O1 C1 1.4398(18) . ?
O1 C7 1.428(2) . ?
O2 C3 1.427(2) . ?
O2 C4 1.417(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.370(2) . ?
C9 C10 1.417(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.368(2) . ?
C16 C15 1.413(2) . ?
C17 H17 0.9500 . ?
C17 C8 1.419(2) . ?
C8 C1 1.505(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.508(2) . ?
C2 C6 1.504(2) . ?
C2 C1 1.525(2) . ?
C15 C10 1.421(2) . ?
C15 C14 1.419(2) . ?
C10 C11 1.421(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.369(3) . ?
C6 C7 1.536(3) . ?
C6 C5 1.306(3) . ?
C1 H1 1.0000 . ?
C14 H14 0.9500 . ?
C14 C13 1.358(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C12 H12 0.9500 . ?
C12 C13 1.401(3) . ?
C13 H13 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.484(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 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
C7 O1 C1 108.50(12) . . ?
C4 O2 C3 112.95(14) . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.07(14) . . ?
C10 C9 H9 119.5 . . ?
C17 C16 H16 119.4 . . ?
C17 C16 C15 121.27(14) . . ?
C15 C16 H16 119.4 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C8 120.15(14) . . ?
C8 C17 H17 119.9 . . ?
C9 C8 C17 119.78(14) . . ?
C9 C8 C1 120.20(13) . . ?
C17 C8 C1 119.97(14) . . ?
C3 C2 H2 109.8 . . ?
C3 C2 C1 117.29(13) . . ?
C6 C2 H2 109.8 . . ?
C6 C2 C3 109.72(13) . . ?
C6 C2 C1 100.05(12) . . ?
C1 C2 H2 109.8 . . ?
C16 C15 C10 118.72(14) . . ?
C16 C15 C14 122.21(15) . . ?
C14 C15 C10 119.06(15) . . ?
C9 C10 C15 119.01(14) . . ?
C9 C10 C11 122.46(16) . . ?
C15 C10 C11 118.52(16) . . ?
O2 C3 C2 109.35(13) . . ?
O2 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.39(18) . . ?
C12 C11 H11 119.8 . . ?
C2 C6 C7 106.98(14) . . ?
C5 C6 C2 122.09(16) . . ?
C5 C6 C7 130.28(16) . . ?
O1 C1 C8 109.85(12) . . ?
O1 C1 C2 103.80(12) . . ?
O1 C1 H1 109.5 . . ?
C8 C1 C2 114.62(12) . . ?
C8 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C15 C14 H14 119.6 . . ?
C13 C14 C15 120.85(19) . . ?
C13 C14 H14 119.6 . . ?
O1 C7 C6 104.31(13) . . ?
O1 C7 H7A 110.9 . . ?
O1 C7 H7B 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.87(17) . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.30(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C6 C5 H5 119.8 . . ?
C6 C5 C4 120.47(17) . . ?
C4 C5 H5 119.8 . . ?
O2 C4 C5 115.78(16) . . ?
O2 C4 H4A 108.3 . . ?
O2 C4 H4B 108.3 . . ?
C5 C4 H4A 108.3 . . ?
C5 C4 H4B 108.3 . . ?
H4A C4 H4B 107.4 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
