# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_mx6186
_audit_block_doi                 10.5517/ccdc.csd.cc1zc5s9
_database_code_depnum_ccdc_archive 'CCDC 1828001'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1063/1.5097192 2019
loop_
_audit_author_name
_audit_author_address
Long IC,CAS
_audit_update_record             
;
2018-03-07 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
_audit_creation_date             2017-08-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H18 S2'
_chemical_formula_sum            'C28 H18 S2'
_chemical_formula_weight         418.54
_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'
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                   22.064(9)
_cell_length_b                   5.688(2)
_cell_length_c                   16.512(7)
_cell_angle_alpha                90
_cell_angle_beta                 105.246(4)
_cell_angle_gamma                90
_cell_volume                     1999.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2964
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4717
_cell_measurement_theta_min      2.5570
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.859
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.80204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            gold
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7817
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         2.557
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2156
_reflns_number_total             2282
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.177
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2282
_refine_ls_number_restraints     263
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.196
_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)+(0.0446P)²+2.9068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 S1A-C11A = S1A-C14A = S1-C11 = S1-C14
 1.76 with sigma of 0.02
 C12A-C11A = C14A-C13A = C12-C11 = C14-C13
 1.33 with sigma of 0.02
 C13A-C12A = C13-C12
 1.46 with sigma of 0.02
 C9A-C10A
 1.32 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim C9 \\sim C10 \\sim C11 \\sim C12 \\sim C13 \\sim C14 \\sim S1A \\sim
C9A \\sim C10A \\sim C11A \\sim C12A \\sim C13A \\sim C14A: within 1.7A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(S1) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq,
Uanis(S1A) \\sim Ueq, Uanis(C9A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C11A)
\\sim Ueq, Uanis(C12A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C14A) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C14A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(S1A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(C12A)=Sof(H12A)=
 Sof(C13A)=Sof(H13A)=Sof(C14A)=Sof(H14A)=1-FVAR(1)
 Sof(S1)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=Sof(C11)=Sof(C12)=Sof(H12)=Sof(C13)=
 Sof(H13)=Sof(C14)=Sof(H14)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13),
 C14(H14), C9A(H9A), C10A(H10A), C12A(H12A), C13A(H13A), C14A(H14A)
;
_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 0.67381(6) 0.4212(3) 0.76489(9) 0.0314(3) Uani 0.698(3) 1 d D U P A 1
C1 C 0.58150(9) 1.0922(3) 0.52516(12) 0.0252(4) Uani 1 1 d . . . . .
C2 C 0.64467(9) 1.0820(4) 0.56782(12) 0.0291(5) Uani 1 1 d . . . . .
H2 H 0.659990 0.960508 0.607383 0.035 Uiso 1 1 calc R . . . .
C3 C 0.68521(9) 1.2525(4) 0.55176(13) 0.0319(5) Uani 1 1 d . . . . .
H3 H 0.728584 1.246604 0.580378 0.038 Uiso 1 1 calc R . . . .
C4 C 0.66301(10) 1.4308(4) 0.49451(13) 0.0325(5) Uani 1 1 d . . . . .
H4 H 0.691221 1.547373 0.485059 0.039 Uiso 1 1 calc R . . . .
C5 C 0.59951(10) 1.4414(4) 0.45038(12) 0.0293(4) Uani 1 1 d . . . . .
H5 H 0.584669 1.563288 0.410784 0.035 Uiso 1 1 calc R . . . .
C6 C 0.55867(9) 1.2724(3) 0.46515(11) 0.0247(4) Uani 1 1 d . . . . .
C7 C 0.52709(9) 0.9501(4) 0.52930(11) 0.0250(4) Uani 1 1 d . . . . .
C8 C 0.51059(9) 0.7585(4) 0.56971(11) 0.0258(4) Uani 1 1 d . . . . .
C9 C 0.55699(17) 0.6332(7) 0.6323(3) 0.0195(8) Uani 0.698(3) 1 d . U P A 1
H9 H 0.598492 0.694393 0.645389 0.023 Uiso 0.698(3) 1 calc R . P A 1
C10 C 0.54813(12) 0.4359(5) 0.67503(15) 0.0193(6) Uani 0.698(3) 1 d . U P A 1
H10 H 0.506714 0.374422 0.663784 0.023 Uiso 0.698(3) 1 calc R . P A 1
C11 C 0.59669(14) 0.3145(5) 0.73566(17) 0.0180(6) Uani 0.698(3) 1 d D U P A 1
C12 C 0.5867(4) 0.0853(12) 0.7828(4) 0.0385(16) Uani 0.698(3) 1 d D U P A 1
H12 H 0.549529 -0.003431 0.778601 0.046 Uiso 0.698(3) 1 calc R . P A 1
C13 C 0.6494(4) 0.046(2) 0.8342(7) 0.0354(18) Uani 0.698(3) 1 d D U P A 1
H13 H 0.657896 -0.087156 0.869994 0.042 Uiso 0.698(3) 1 calc R . P A 1
C14 C 0.6965(5) 0.197(2) 0.8323(10) 0.037(3) Uani 0.698(3) 1 d D U P A 1
H14 H 0.738350 0.178503 0.865955 0.045 Uiso 0.698(3) 1 calc R . P A 1
S1A S 0.59066(18) 0.1476(7) 0.7630(3) 0.0395(11) Uani 0.302(3) 1 d D U P A 2
C9A C 0.5400(5) 0.572(2) 0.6344(8) 0.038(3) Uani 0.302(3) 1 d D U P A 2
H9A H 0.514779 0.444715 0.643310 0.046 Uiso 0.302(3) 1 calc R . P A 2
C10A C 0.5950(5) 0.5809(18) 0.6754(6) 0.061(2) Uani 0.302(3) 1 d D U P A 2
H10A H 0.620320 0.709721 0.667600 0.073 Uiso 0.302(3) 1 calc R . P A 2
C11A C 0.6237(5) 0.3922(16) 0.7379(5) 0.0399(19) Uani 0.302(3) 1 d D U P A 2
C12A C 0.6855(8) 0.390(3) 0.7807(11) 0.060(5) Uani 0.302(3) 1 d D U P A 2
H12A H 0.713324 0.515184 0.777305 0.072 Uiso 0.302(3) 1 calc R . P A 2
C13A C 0.7052(12) 0.188(5) 0.831(2) 0.026(3) Uani 0.302(3) 1 d D U P A 2
H13A H 0.747422 0.162969 0.861812 0.031 Uiso 0.302(3) 1 calc R . P A 2
C14A C 0.6588(8) 0.037(5) 0.8297(15) 0.025(3) Uani 0.302(3) 1 d D U P A 2
H14A H 0.662511 -0.106584 0.860198 0.030 Uiso 0.302(3) 1 calc R . P A 2


_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 C11 1.751(3) . ?
S1 C14 1.678(9) . ?
C1 C2 1.388(3) . ?
C1 C6 1.423(3) . ?
C1 C7 1.464(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.400(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(3) . ?
C6 C8 1.495(3) 5_676 ?
C7 C7 1.442(4) 5_676 ?
C7 C8 1.376(3) . ?
C8 C9 1.438(4) . ?
C8 C9A 1.523(13) . ?
C9 H9 0.9500 . ?
C9 C10 1.367(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.436(4) . ?
C11 C12 1.563(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.437(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.356(9) . ?
C14 H14 0.9500 . ?
S1A C11A 1.672(10) . ?
S1A C14A 1.732(15) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.226(12) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.508(14) . ?
C11A C12A 1.361(14) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.413(18) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.336(18) . ?
C14A H14A 0.9500 . ?

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
C14 S1 C11 91.1(4) . . ?
C2 C1 C6 120.53(18) . . ?
C2 C1 C7 132.84(18) . . ?
C6 C1 C7 106.61(16) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.98(19) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.71(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.84(19) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.18(19) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C8 108.80(16) . 5_676 ?
C5 C6 C1 119.75(18) . . ?
C5 C6 C8 131.41(18) . 5_676 ?
C7 C7 C1 107.3(2) 5_676 . ?
C8 C7 C1 141.71(18) . . ?
C8 C7 C7 111.0(2) . 5_676 ?
C6 C8 C9A 113.1(4) 5_676 . ?
C7 C8 C6 106.28(16) . 5_676 ?
C7 C8 C9 120.8(2) . . ?
C7 C8 C9A 140.6(4) . . ?
C9 C8 C6 132.9(2) . 5_676 ?
C8 C9 H9 116.3 . . ?
C10 C9 C8 127.3(3) . . ?
C10 C9 H9 116.3 . . ?
C9 C10 H10 117.5 . . ?
C9 C10 C11 125.0(3) . . ?
C11 C10 H10 117.5 . . ?
C10 C11 S1 121.2(2) . . ?
C10 C11 C12 124.8(4) . . ?
C12 C11 S1 114.0(3) . . ?
C11 C12 H12 129.7 . . ?
C13 C12 C11 100.6(7) . . ?
C13 C12 H12 129.7 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.9(10) . . ?
C14 C13 H13 119.6 . . ?
S1 C14 H14 123.2 . . ?
C13 C14 S1 113.5(9) . . ?
C13 C14 H14 123.2 . . ?
C11A S1A C14A 95.7(9) . . ?
C8 C9A H9A 118.7 . . ?
C10A C9A C8 122.6(10) . . ?
C10A C9A H9A 118.7 . . ?
C9A C10A H10A 119.1 . . ?
C9A C10A C11A 121.7(11) . . ?
C11A C10A H10A 119.1 . . ?
C10A C11A S1A 129.1(8) . . ?
C12A C11A S1A 107.9(10) . . ?
C12A C11A C10A 122.9(11) . . ?
C11A C12A H12A 122.5 . . ?
C11A C12A C13A 114.9(18) . . ?
C13A C12A H12A 122.5 . . ?
C12A C13A H13A 123.2 . . ?
C14A C13A C12A 114(2) . . ?
C14A C13A H13A 123.2 . . ?
S1A C14A H14A 126.1 . . ?
C13A C14A S1A 107.8(19) . . ?
C13A C14A H14A 126.1 . . ?

_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_mx5932
_database_code_depnum_ccdc_archive 'CCDC 1580864'
_audit_update_record             
;
2017-10-19 deposited with the CCDC.	2020-10-07 downloaded from the CCDC.
;
_audit_creation_date             2017-05-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H26 O2'
_chemical_formula_sum            'C34 H26 O2'
_chemical_formula_weight         466.55
_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'
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                   5.2200(10)
_cell_length_b                   10.511(2)
_cell_length_c                   11.768(2)
_cell_angle_alpha                70.25(3)
_cell_angle_beta                 80.71(3)
_cell_angle_gamma                80.17(3)
_cell_volume                     595.0(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1926
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4842
_cell_measurement_theta_min      2.0749
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needke
_exptl_crystal_F_000             246
_exptl_crystal_size_max          0.488
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8276
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         1.850
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2459
_reflns_number_total             2719
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.194
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.194
_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)+(0.0479P)²+0.2235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1433
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.0193(3) 0.10879(13) 0.10788(12) 0.0361(3) Uani 1 1 d . . . . .
C1 C -0.1496(4) 0.00453(19) 0.15307(18) 0.0351(4) Uani 1 1 d . . . . .
H1A H -0.231064 -0.000319 0.087366 0.053 Uiso 1 1 calc GR . . . .
H1B H -0.281784 0.025415 0.213254 0.053 Uiso 1 1 calc GR . . . .
H1C H -0.049240 -0.081475 0.188907 0.053 Uiso 1 1 calc GR . . . .
C2 C 0.1353(3) 0.13771(17) 0.19134(15) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.1330(3) 0.06078(17) 0.31252(16) 0.0281(4) Uani 1 1 d . . . . .
H3 H 0.049387 -0.017255 0.343174 0.034 Uiso 1 1 calc R . . . .
C4 C 0.2574(3) 0.10145(17) 0.38829(16) 0.0279(4) Uani 1 1 d . . . . .
H4 H 0.251981 0.050282 0.470179 0.033 Uiso 1 1 calc R . . . .
C5 C 0.3899(3) 0.21615(16) 0.34591(15) 0.0251(4) Uani 1 1 d . . . . .
C6 C 0.3915(3) 0.29066(17) 0.22188(15) 0.0277(4) Uani 1 1 d . . . . .
H6 H 0.479426 0.367185 0.190043 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2655(3) 0.25284(17) 0.14626(16) 0.0290(4) Uani 1 1 d . . . . .
H7 H 0.267529 0.304555 0.064596 0.035 Uiso 1 1 calc R . . . .
C8 C 0.5108(3) 0.25462(16) 0.43113(16) 0.0271(4) Uani 1 1 d . . . . .
H8 H 0.482004 0.204139 0.512858 0.032 Uiso 1 1 calc R . . . .
C9 C 0.6597(3) 0.35596(17) 0.40290(16) 0.0261(4) Uani 1 1 d . . . . .
H9 H 0.689433 0.404895 0.320817 0.031 Uiso 1 1 calc R . . . .
C10 C 0.7789(3) 0.39783(16) 0.48493(15) 0.0241(4) Uani 1 1 d . . . . .
C11 C 0.9568(3) 0.49095(16) 0.44830(15) 0.0239(4) Uani 1 1 d . . . . .
C12 C 1.0943(3) 0.57786(16) 0.33913(15) 0.0238(4) Uani 1 1 d . . . . .
C13 C 1.0946(3) 0.59796(17) 0.21702(16) 0.0267(4) Uani 1 1 d . . . . .
H13 H 0.983095 0.555582 0.191322 0.032 Uiso 1 1 calc R . . . .
C14 C 1.2642(3) 0.68266(17) 0.13234(16) 0.0308(4) Uani 1 1 d . . . . .
H14 H 1.264842 0.697386 0.049805 0.037 Uiso 1 1 calc R . . . .
C15 C 1.4311(3) 0.74465(17) 0.17119(16) 0.0305(4) Uani 1 1 d . . . . .
H15 H 1.545982 0.799115 0.114240 0.037 Uiso 1 1 calc R . . . .
C16 C 1.4301(3) 0.72688(17) 0.29439(16) 0.0283(4) Uani 1 1 d . . . . .
H16 H 1.542416 0.769736 0.319072 0.034 Uiso 1 1 calc R . . . .
C17 C 1.2600(3) 0.64472(16) 0.37979(15) 0.0244(4) 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
O1 C1 1.430(2) . ?
O1 C2 1.3710(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.381(2) . ?
C2 C7 1.392(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.392(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.396(2) . ?
C5 C6 1.403(2) . ?
C5 C8 1.460(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(2) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.345(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.445(2) . ?
C10 C11 1.379(2) . ?
C10 C17 1.490(2) 2_766 ?
C11 C11 1.443(3) 2_766 ?
C11 C12 1.461(2) . ?
C12 C13 1.380(2) . ?
C12 C17 1.428(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.398(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.397(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?

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
C2 O1 C1 117.33(14) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.76(15) . . ?
O1 C2 C7 115.49(15) . . ?
C3 C2 C7 119.74(15) . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.21(15) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 118.8 . . ?
C3 C4 C5 122.44(16) . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 116.76(15) . . ?
C4 C5 C8 119.48(15) . . ?
C6 C5 C8 123.74(15) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.41(15) . . ?
C7 C6 H6 119.3 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.43(16) . . ?
C6 C7 H7 119.8 . . ?
C5 C8 H8 116.8 . . ?
C9 C8 C5 126.33(16) . . ?
C9 C8 H8 116.8 . . ?
C8 C9 H9 116.1 . . ?
C8 C9 C10 127.73(17) . . ?
C10 C9 H9 116.1 . . ?
C9 C10 C17 129.51(15) . 2_766 ?
C11 C10 C9 124.30(16) . . ?
C11 C10 C17 106.19(14) . 2_766 ?
C10 C11 C11 110.95(19) . 2_766 ?
C10 C11 C12 141.60(15) . . ?
C11 C11 C12 107.44(17) 2_766 . ?
C13 C12 C11 132.61(15) . . ?
C13 C12 C17 120.97(15) . . ?
C17 C12 C11 106.37(14) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.33(16) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.08(17) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.4 . . ?
C14 C15 C16 121.21(16) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.54(16) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C10 109.02(14) . 2_766 ?
C16 C17 C10 132.03(15) . 2_766 ?
C16 C17 C12 118.84(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
