# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_201016_ms586_052_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2049425'
loop_
_audit_author_name
_audit_author_address
'Muhammad Suleman'
;zhejiang university
China
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_audit_creation_date             2020-10-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 F N O4 S'
_chemical_formula_sum            'C24 H18 F N O4 S'
_chemical_formula_weight         435.45
_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      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                   7.1439(14)
_cell_length_b                   10.734(2)
_cell_length_c                   14.451(3)
_cell_angle_alpha                72.259(9)
_cell_angle_beta                 81.410(9)
_cell_angle_gamma                72.811(10)
_cell_volume                     1006.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9861
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.13
_cell_measurement_theta_min      2.19
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.7200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0895 before and 0.0376 after correction.
The Ratio of minimum to maximum transmission is 0.9658.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            25179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.080
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4172
_reflns_number_total             4409
_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 V8.40B (?, 2016)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (?, 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         0.311
_refine_diff_density_min         -0.399
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.4833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0871
_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:
 C7(H7A,H7B), C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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 0.26413(4) 0.61063(3) 0.88994(2) 0.01960(9) Uani 1 1 d . . . . .
F1 F 1.09421(12) 0.35198(10) 0.51797(6) 0.0384(2) Uani 1 1 d . . . . .
O1 O 0.15943(14) 0.58479(9) 0.98393(6) 0.0272(2) Uani 1 1 d . . . . .
O2 O 0.42095(14) 0.67331(9) 0.87681(7) 0.0271(2) Uani 1 1 d . . . . .
O3 O 0.48301(14) 0.55295(9) 0.72047(6) 0.0251(2) Uani 1 1 d . . . . .
O4 O 1.08032(14) 0.36332(12) 0.72738(8) 0.0362(2) Uani 1 1 d . . . . .
N1 N 0.35334(15) 0.45693(10) 0.86915(7) 0.0187(2) Uani 1 1 d . . . . .
C1 C 0.25770(19) 0.11538(13) 0.95506(9) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.161950 0.128010 1.006950 0.030 Uiso 1 1 calc R . . . .
C2 C 0.3001(2) -0.00227(14) 0.92601(10) 0.0302(3) Uani 1 1 d . . . . .
H2 H 0.232148 -0.069432 0.957269 0.036 Uiso 1 1 calc R . . . .
C3 C 0.4425(2) -0.02184(14) 0.85093(10) 0.0318(3) Uani 1 1 d . . . . .
H3 H 0.474641 -0.103574 0.832225 0.038 Uiso 1 1 calc R . . . .
C4 C 0.5374(2) 0.07816(13) 0.80348(9) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.633256 0.064965 0.751739 0.032 Uiso 1 1 calc R . . . .
C5 C 0.49322(17) 0.19821(12) 0.83112(8) 0.0190(2) Uani 1 1 d . . . . .
C6 C 0.35521(17) 0.21568(12) 0.90834(8) 0.0192(2) Uani 1 1 d . . . . .
C7 C 0.31602(19) 0.33722(12) 0.94613(9) 0.0235(3) Uani 1 1 d . . . . .
H7A H 0.177666 0.359679 0.972185 0.028 Uiso 1 1 calc R . . . .
H7B H 0.401030 0.315117 1.000233 0.028 Uiso 1 1 calc R . . . .
C8 C 0.46996(17) 0.45041(12) 0.78405(8) 0.0183(2) Uani 1 1 d . . . . .
C9 C 0.59431(17) 0.30901(12) 0.77786(8) 0.0180(2) Uani 1 1 d . . . . .
C10 C 0.79687(18) 0.28912(13) 0.81749(9) 0.0233(2) Uani 1 1 d . . . . .
H10A H 0.782150 0.346545 0.861666 0.028 Uiso 1 1 calc R . . . .
H10B H 0.851292 0.193136 0.853455 0.028 Uiso 1 1 calc R . . . .
C11 C 0.93100(18) 0.33170(13) 0.72730(9) 0.0238(3) Uani 1 1 d . . . . .
C12 C 0.83931(18) 0.32834(12) 0.64270(9) 0.0217(2) Uani 1 1 d . . . . .
C13 C 0.64854(17) 0.31606(11) 0.67014(8) 0.0188(2) Uani 1 1 d . . . . .
C14 C 0.52669(18) 0.31772(12) 0.60290(9) 0.0220(2) Uani 1 1 d . . . . .
H14 H 0.396887 0.309341 0.622190 0.026 Uiso 1 1 calc R . . . .
C15 C 0.6006(2) 0.33205(13) 0.50631(9) 0.0258(3) Uani 1 1 d . . . . .
H15 H 0.519177 0.333626 0.459414 0.031 Uiso 1 1 calc R . . . .
C16 C 0.7914(2) 0.34414(14) 0.47689(9) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.839577 0.353811 0.410862 0.033 Uiso 1 1 calc R . . . .
C17 C 0.90819(19) 0.34179(13) 0.54532(9) 0.0260(3) Uani 1 1 d . . . . .
C18 C 0.09602(18) 0.70462(12) 0.79977(9) 0.0210(2) Uani 1 1 d . . . . .
C19 C 0.1232(2) 0.82448(13) 0.73487(10) 0.0293(3) Uani 1 1 d . . . . .
H19 H 0.233285 0.855414 0.737750 0.035 Uiso 1 1 calc R . . . .
C20 C -0.0137(2) 0.89850(14) 0.66549(11) 0.0325(3) Uani 1 1 d . . . . .
H20 H 0.002079 0.981566 0.621689 0.039 Uiso 1 1 calc R . . . .
C21 C -0.1733(2) 0.85265(14) 0.65934(10) 0.0282(3) Uani 1 1 d . . . . .
C22 C -0.19689(19) 0.73205(14) 0.72544(10) 0.0286(3) Uani 1 1 d . . . . .
H22 H -0.305433 0.700054 0.721824 0.034 Uiso 1 1 calc R . . . .
C23 C -0.06442(19) 0.65787(13) 0.79649(9) 0.0258(3) Uani 1 1 d . . . . .
H23 H -0.082997 0.576701 0.842020 0.031 Uiso 1 1 calc R . . . .
C24 C -0.3187(2) 0.93119(17) 0.58234(12) 0.0417(4) Uani 1 1 d . . . . .
H24A H -0.301785 0.881678 0.533507 0.063 Uiso 1 1 calc GR . . . .
H24B H -0.295938 1.020715 0.550900 0.063 Uiso 1 1 calc GR . . . .
H24C H -0.452513 0.942098 0.612691 0.063 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 O1 1.4390(9) . ?
S1 O2 1.4312(10) . ?
S1 N1 1.6858(10) . ?
S1 C18 1.7631(13) . ?
F1 C17 1.3553(15) . ?
O3 C8 1.2179(15) . ?
O4 C11 1.2115(16) . ?
N1 C7 1.4841(15) . ?
N1 C8 1.3869(15) . ?
C1 H1 0.9500 . ?
C1 C2 1.3864(19) . ?
C1 C6 1.4000(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3873(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3984(17) . ?
C5 C6 1.3936(16) . ?
C5 C9 1.5206(16) . ?
C6 C7 1.5005(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5372(16) . ?
C9 C10 1.5678(16) . ?
C9 C13 1.5313(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5326(17) . ?
C11 C12 1.4850(17) . ?
C12 C13 1.3946(17) . ?
C12 C17 1.3981(17) . ?
C13 C14 1.3910(17) . ?
C14 H14 0.9500 . ?
C14 C15 1.3956(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3979(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3760(19) . ?
C18 C19 1.3896(18) . ?
C18 C23 1.3923(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(2) . ?
C21 C22 1.394(2) . ?
C21 C24 1.5112(19) . ?
C22 H22 0.9500 . ?
C22 C23 1.3895(19) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
O1 S1 N1 104.54(5) . . ?
O1 S1 C18 109.49(6) . . ?
O2 S1 O1 118.41(6) . . ?
O2 S1 N1 109.20(5) . . ?
O2 S1 C18 109.29(6) . . ?
N1 S1 C18 105.02(5) . . ?
C7 N1 S1 118.15(8) . . ?
C8 N1 S1 117.15(8) . . ?
C8 N1 C7 124.50(10) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.36(12) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.89(12) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.92(12) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.61(12) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C9 120.63(11) . . ?
C6 C5 C4 119.35(11) . . ?
C6 C5 C9 120.02(10) . . ?
C1 C6 C7 118.93(11) . . ?
C5 C6 C1 119.82(11) . . ?
C5 C6 C7 121.17(10) . . ?
N1 C7 C6 111.91(10) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
O3 C8 N1 121.22(11) . . ?
O3 C8 C9 121.80(10) . . ?
N1 C8 C9 116.79(10) . . ?
C5 C9 C8 112.51(9) . . ?
C5 C9 C10 113.91(10) . . ?
C5 C9 C13 113.43(9) . . ?
C8 C9 C10 105.67(9) . . ?
C13 C9 C8 107.83(9) . . ?
C13 C9 C10 102.71(9) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 105.51(10) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
O4 C11 C10 125.34(12) . . ?
O4 C11 C12 128.13(12) . . ?
C12 C11 C10 106.52(10) . . ?
C13 C12 C11 109.98(10) . . ?
C13 C12 C17 118.67(11) . . ?
C17 C12 C11 131.27(12) . . ?
C12 C13 C9 111.69(10) . . ?
C14 C13 C9 126.76(11) . . ?
C14 C13 C12 121.47(11) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.11(11) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.60(12) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.6 . . ?
C17 C16 C15 118.79(11) . . ?
C17 C16 H16 120.6 . . ?
F1 C17 C12 119.24(12) . . ?
F1 C17 C16 119.40(11) . . ?
C16 C17 C12 121.36(12) . . ?
C19 C18 S1 119.85(10) . . ?
C19 C18 C23 121.29(12) . . ?
C23 C18 S1 118.85(10) . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.84(12) . . ?
C20 C19 H19 120.6 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.04(13) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C22 118.86(12) . . ?
C20 C21 C24 120.96(13) . . ?
C22 C21 C24 120.18(13) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.14(12) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 120.6 . . ?
C22 C23 C18 118.81(12) . . ?
C22 C23 H23 120.6 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_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_200723_ms586_004_2_0m
_database_code_depnum_ccdc_archive 'CCDC 2049422'
loop_
_audit_author_name
_audit_author_address
'Muhammad Suleman'
;zhejiang university
China
;
_audit_update_record             
;
2020-12-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;
_audit_creation_date             2020-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O3'
_chemical_formula_sum            'C17 H12 O3'
_chemical_formula_weight         264.27
_chemical_absolute_configuration unk
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.849(4)
_cell_length_b                   8.586(3)
_cell_length_c                   12.730(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.872(14)
_cell_angle_gamma                90
_cell_volume                     1290.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6661
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.87
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3769
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1633 before and 0.0897 after correction.
The Ratio of minimum to maximum transmission is 0.5056.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0564
_diffrn_reflns_av_unetI/netI     0.0903
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12035
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.924
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.016
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'zju Bruker D8 Venture Ims3.0'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.861
_reflns_Friedel_fraction_max     0.841
_reflns_number_gt                4868
_reflns_number_total             5216
_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
_computing.data_collection       Bruker
_computing.data_reduction        SAINT
_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         0.968
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.186
_refine_ls_abs_structure_details 
;
 Flack x determined using 1852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5216
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0791
_refine_ls_restrained_S_all      1.086
_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)+(0.1253P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1783
_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 Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C25(H25A,H25B), C28(H28A,H28B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21), C31(H31), C32(H32), C33(H33), C34(H34)
;
_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 -0.5245(2) 1.2279(4) 0.8172(3) 0.0521(8) Uani 1 1 d . . . . .
O2 O -0.2549(2) 1.1034(3) 0.56628(19) 0.0431(7) Uani 1 1 d . . . . .
O3 O -0.1571(2) 1.3204(3) 0.58631(18) 0.0368(6) Uani 1 1 d . . . . .
C1 C -0.4213(3) 0.9052(5) 0.8523(3) 0.0363(7) Uani 1 1 d . . . . .
H1 H -0.495546 0.905648 0.875044 0.044 Uiso 1 1 calc R . . . .
C2 C -0.3567(3) 0.7712(4) 0.8588(3) 0.0367(7) Uani 1 1 d . . . . .
H2 H -0.386149 0.678272 0.886403 0.044 Uiso 1 1 calc R . . . .
C3 C -0.2468(3) 0.7728(4) 0.8243(3) 0.0334(7) Uani 1 1 d . . . . .
H3 H -0.202663 0.680307 0.828654 0.040 Uiso 1 1 calc R . . . .
C4 C -0.2018(3) 0.9079(4) 0.7840(3) 0.0301(7) Uani 1 1 d . . . . .
H4 H -0.127878 0.907823 0.760410 0.036 Uiso 1 1 calc R . . . .
C5 C -0.2668(2) 1.0424(4) 0.7788(2) 0.0246(6) Uani 1 1 d . . . . .
C6 C -0.3757(2) 1.0395(4) 0.8117(2) 0.0279(6) Uani 1 1 d . . . . .
C7 C -0.4287(3) 1.1946(4) 0.7992(3) 0.0328(7) Uani 1 1 d . . . . .
C8 C -0.3418(3) 1.3064(4) 0.7596(3) 0.0340(7) Uani 1 1 d . . . . .
H8A H -0.323320 1.390051 0.811784 0.041 Uiso 1 1 calc R . . . .
H8B H -0.371280 1.354649 0.692103 0.041 Uiso 1 1 calc R . . . .
C9 C -0.2335(2) 1.2048(4) 0.7437(2) 0.0264(6) Uani 1 1 d . . . . .
C10 C -0.2159(3) 1.2038(4) 0.6250(2) 0.0299(7) Uani 1 1 d . . . . .
C11 C -0.1159(3) 1.4475(4) 0.6550(3) 0.0379(7) Uani 1 1 d . . . . .
H11A H -0.178724 1.520924 0.664180 0.045 Uiso 1 1 calc R . . . .
H11B H -0.055903 1.504881 0.621602 0.045 Uiso 1 1 calc R . . . .
C12 C -0.0691(3) 1.3887(4) 0.7615(3) 0.0319(7) Uani 1 1 d . . . . .
C13 C -0.1275(2) 1.2683(4) 0.8060(2) 0.0267(6) Uani 1 1 d . . . . .
C14 C -0.0884(3) 1.2113(4) 0.9051(2) 0.0317(7) Uani 1 1 d . . . . .
H14 H -0.128228 1.129871 0.936342 0.038 Uiso 1 1 calc R . . . .
C15 C 0.0090(3) 1.2736(5) 0.9585(3) 0.0369(7) Uani 1 1 d . . . . .
H15 H 0.034750 1.235462 1.026393 0.044 Uiso 1 1 calc R . . . .
C16 C 0.0681(3) 1.3909(5) 0.9125(3) 0.0388(8) Uani 1 1 d . . . . .
H16 H 0.135530 1.431277 0.948062 0.047 Uiso 1 1 calc R . . . .
C17 C 0.0285(3) 1.4498(4) 0.8139(3) 0.0376(8) Uani 1 1 d . . . . .
H17 H 0.068334 1.531477 0.782804 0.045 Uiso 1 1 calc R . . . .
O4 O 0.2554(3) 0.9948(4) 0.98943(19) 0.0484(7) Uani 1 1 d . . . . .
O5 O 0.03331(19) 0.8087(4) 0.6643(2) 0.0399(6) Uani 1 1 d . . . . .
O6 O 0.03886(19) 1.0441(3) 0.5971(2) 0.0390(6) Uani 1 1 d . . . . .
C18 C 0.3263(3) 0.6736(4) 0.9121(2) 0.0336(7) Uani 1 1 d . . . . .
H18 H 0.340480 0.677501 0.986636 0.040 Uiso 1 1 calc R . . . .
C19 C 0.3515(3) 0.5423(5) 0.8566(3) 0.0387(8) Uani 1 1 d . . . . .
H19 H 0.384083 0.454424 0.893057 0.046 Uiso 1 1 calc R . . . .
C20 C 0.3292(3) 0.5374(5) 0.7454(3) 0.0372(7) Uani 1 1 d . . . . .
H20 H 0.346755 0.445867 0.708148 0.045 Uiso 1 1 calc R . . . .
C21 C 0.2819(3) 0.6647(4) 0.6902(2) 0.0326(7) Uani 1 1 d . . . . .
H21 H 0.266700 0.660691 0.615761 0.039 Uiso 1 1 calc R . . . .
C22 C 0.2574(2) 0.7982(4) 0.7463(2) 0.0263(6) Uani 1 1 d . . . . .
C23 C 0.2792(2) 0.8014(4) 0.8556(2) 0.0279(6) Uani 1 1 d . . . . .
C24 C 0.2477(3) 0.9535(4) 0.8969(2) 0.0303(6) Uani 1 1 d . . . . .
C25 C 0.2029(3) 1.0551(4) 0.8042(2) 0.0310(6) Uani 1 1 d . . . . .
H25A H 0.250087 1.149649 0.799731 0.037 Uiso 1 1 calc R . . . .
H25B H 0.123795 1.087376 0.812043 0.037 Uiso 1 1 calc R . . . .
C26 C 0.2091(2) 0.9515(4) 0.7032(2) 0.0251(6) Uani 1 1 d . . . . .
C27 C 0.0872(2) 0.9251(4) 0.6531(2) 0.0291(6) Uani 1 1 d . . . . .
C28 C 0.1033(3) 1.1854(5) 0.5831(3) 0.0399(8) Uani 1 1 d . . . . .
H28A H 0.103000 1.250571 0.647269 0.048 Uiso 1 1 calc R . . . .
H28B H 0.066947 1.245674 0.523157 0.048 Uiso 1 1 calc R . . . .
C29 C 0.2234(3) 1.1491(4) 0.5626(3) 0.0343(7) Uani 1 1 d . . . . .
C30 C 0.2776(3) 1.0291(4) 0.6212(2) 0.0272(6) Uani 1 1 d . . . . .
C31 C 0.3881(3) 0.9894(5) 0.6045(3) 0.0366(8) Uani 1 1 d . . . . .
H31 H 0.425200 0.907820 0.644370 0.044 Uiso 1 1 calc R . . . .
C32 C 0.4448(3) 1.0689(6) 0.5294(3) 0.0476(9) Uani 1 1 d . . . . .
H32 H 0.520386 1.041363 0.517896 0.057 Uiso 1 1 calc R . . . .
C33 C 0.3908(4) 1.1887(6) 0.4713(4) 0.0561(12) Uani 1 1 d . . . . .
H33 H 0.429648 1.243343 0.420460 0.067 Uiso 1 1 calc R . . . .
C34 C 0.2800(4) 1.2284(5) 0.4876(3) 0.0479(9) Uani 1 1 d . . . . .
H34 H 0.242907 1.309791 0.447587 0.057 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 C7 1.212(4) . ?
O2 C10 1.206(4) . ?
O3 C10 1.338(4) . ?
O3 C11 1.457(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.380(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.409(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(5) . ?
C5 C6 1.390(4) . ?
C5 C9 1.526(4) . ?
C6 C7 1.475(5) . ?
C7 C8 1.525(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.578(4) . ?
C9 C10 1.544(4) . ?
C9 C13 1.528(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.507(5) . ?
C12 C13 1.391(4) . ?
C12 C17 1.389(5) . ?
C13 C14 1.395(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.397(5) . ?
C17 H17 0.9500 . ?
O4 C24 1.226(4) . ?
O5 C27 1.201(4) . ?
O6 C27 1.345(4) . ?
O6 C28 1.453(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.376(5) . ?
C18 C23 1.401(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.419(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.394(4) . ?
C22 C23 1.395(4) . ?
C22 C26 1.519(4) . ?
C23 C24 1.468(5) . ?
C24 C25 1.526(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.570(4) . ?
C26 C27 1.545(4) . ?
C26 C30 1.528(4) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.501(5) . ?
C29 C30 1.397(5) . ?
C29 C34 1.390(5) . ?
C30 C31 1.387(5) . ?
C31 H31 0.9500 . ?
C31 C32 1.393(5) . ?
C32 H32 0.9500 . ?
C32 C33 1.390(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.389(7) . ?
C34 H34 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
C10 O3 C11 119.9(2) . . ?
C2 C1 H1 120.6 . . ?
C2 C1 C6 118.9(3) . . ?
C6 C1 H1 120.6 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C9 128.2(3) . . ?
C6 C5 C9 112.0(3) . . ?
C1 C6 C7 127.8(3) . . ?
C5 C6 C1 121.8(3) . . ?
C5 C6 C7 110.4(3) . . ?
O1 C7 C6 126.2(3) . . ?
O1 C7 C8 125.7(3) . . ?
C6 C7 C8 108.1(3) . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
C7 C8 C9 105.8(3) . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
C5 C9 C8 103.6(2) . . ?
C5 C9 C10 109.9(2) . . ?
C5 C9 C13 113.3(2) . . ?
C10 C9 C8 107.9(2) . . ?
C13 C9 C8 112.2(3) . . ?
C13 C9 C10 109.6(2) . . ?
O2 C10 O3 119.4(3) . . ?
O2 C10 C9 122.3(3) . . ?
O3 C10 C9 118.3(3) . . ?
O3 C11 H11A 109.3 . . ?
O3 C11 H11B 109.3 . . ?
O3 C11 C12 111.6(3) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C13 C12 C11 117.2(3) . . ?
C17 C12 C11 122.2(3) . . ?
C17 C12 C13 120.5(3) . . ?
C12 C13 C9 118.0(3) . . ?
C12 C13 C14 119.4(3) . . ?
C14 C13 C9 122.6(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0(3) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 119.8(3) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C27 O6 C28 119.6(2) . . ?
C19 C18 H18 120.9 . . ?
C19 C18 C23 118.2(3) . . ?
C23 C18 H18 120.9 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 120.9(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.7 . . ?
C20 C21 C22 118.7(3) . . ?
C22 C21 H21 120.7 . . ?
C21 C22 C23 119.9(3) . . ?
C21 C22 C26 128.1(2) . . ?
C23 C22 C26 112.1(3) . . ?
C18 C23 C24 128.0(3) . . ?
C22 C23 C18 121.9(3) . . ?
C22 C23 C24 110.1(3) . . ?
O4 C24 C23 126.9(3) . . ?
O4 C24 C25 124.8(3) . . ?
C23 C24 C25 108.3(2) . . ?
C24 C25 H25A 110.6 . . ?
C24 C25 H25B 110.6 . . ?
C24 C25 C26 105.8(3) . . ?
H25A C25 H25B 108.7 . . ?
C26 C25 H25A 110.6 . . ?
C26 C25 H25B 110.6 . . ?
C22 C26 C25 103.8(2) . . ?
C22 C26 C27 109.4(3) . . ?
C22 C26 C30 114.7(2) . . ?
C27 C26 C25 108.3(2) . . ?
C30 C26 C25 112.1(3) . . ?
C30 C26 C27 108.3(2) . . ?
O5 C27 O6 119.2(3) . . ?
O5 C27 C26 124.1(3) . . ?
O6 C27 C26 116.6(3) . . ?
O6 C28 H28A 109.4 . . ?
O6 C28 H28B 109.4 . . ?
O6 C28 C29 111.3(3) . . ?
H28A C28 H28B 108.0 . . ?
C29 C28 H28A 109.4 . . ?
C29 C28 H28B 109.4 . . ?
C30 C29 C28 117.4(3) . . ?
C34 C29 C28 122.5(4) . . ?
C34 C29 C30 120.1(4) . . ?
C29 C30 C26 116.1(3) . . ?
C31 C30 C26 124.1(3) . . ?
C31 C30 C29 119.8(3) . . ?
C30 C31 H31 120.0 . . ?
C30 C31 C32 120.1(4) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.0(4) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0(4) . . ?
C34 C33 H33 120.0 . . ?
C29 C34 H34 120.0 . . ?
C33 C34 C29 119.9(4) . . ?
C33 C34 H34 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
