# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo_dm16027_0m
_database_code_depnum_ccdc_archive 'CCDC 1528081'
_audit_update_record             
;
2017-01-17 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_audit_creation_date             2016-01-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H31 N O2 S'
_chemical_formula_sum            'C23 H31 N O2 S'
_chemical_formula_weight         385.55
_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'
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                   6.812(5)
_cell_length_b                   11.371(8)
_cell_length_c                   13.441(9)
_cell_angle_alpha                80.287(13)
_cell_angle_beta                 84.840(13)
_cell_angle_gamma                77.986(12)
_cell_volume                     1002.2(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1419
_cell_measurement_temperature    130
_cell_measurement_theta_max      26.892
_cell_measurement_theta_min      2.577
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.6007
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1104 before and 0.0442 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1108 before and 0.0457 after correction.
 The Ratio of minimum to maximum transmission is 0.66.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 14550 reflections, Rint = 0.0563
 (6962 with I > 3sig(I), Rint = 0.0470)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            ?
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.678
_diffrn_reflns_theta_min         1.540
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                3489
_reflns_number_total             4638
_reflns_special_details          
;
 Data were apparently pre-merged, so _diffrn_reflns_number
 etc. will have to be added later.
 
 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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.071
_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)+(0.0571P)²+0.5970P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1388
_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), C5(H5), C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C8(H8A,H8B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C10(H10), C18(H18), C19(H19), C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C23(H23A,H23B,H23C)
;
_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 0.38079(8) 0.30003(5) 0.02767(4) 0.01971(15) Uani 1 1 d . . . . .
O1 O 0.5801(2) 0.24647(14) 0.05763(12) 0.0266(4) Uani 1 1 d . . . . .
O2 O 0.2260(2) 0.34027(15) 0.10066(12) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.4005(3) 0.41600(16) -0.05631(13) 0.0191(4) Uani 1 1 d . . . . .
C1 C 0.2191(3) 0.4962(2) -0.10012(17) 0.0233(5) Uani 1 1 d . . . . .
H1A H 0.1959 0.5770 -0.0781 0.028 Uiso 1 1 calc R . . . .
H1B H 0.0988 0.4597 -0.0799 0.028 Uiso 1 1 calc R . . . .
C2 C 0.2654(3) 0.5065(2) -0.21388(17) 0.0228(5) Uani 1 1 d . . . . .
H2 H 0.1936 0.5866 -0.2488 0.027 Uiso 1 1 calc R . . . .
C3 C 0.2143(3) 0.4049(2) -0.25685(18) 0.0260(5) Uani 1 1 d . . . . .
H3 H 0.0859 0.3850 -0.2384 0.031 Uiso 1 1 calc R . . . .
C4 C 0.3362(4) 0.3407(2) -0.31905(18) 0.0271(5) Uani 1 1 d . . . . .
H4 H 0.2905 0.2758 -0.3401 0.033 Uiso 1 1 calc R . . . .
C5 C 0.5404(4) 0.3618(2) -0.35890(18) 0.0266(5) Uani 1 1 d . . . . .
H5 H 0.5350 0.3815 -0.4341 0.032 Uiso 1 1 calc R . . . .
C6 C 0.5878(3) 0.4720(2) -0.32422(17) 0.0227(5) Uani 1 1 d . . . . .
C7 C 0.4944(3) 0.50090(19) -0.22318(16) 0.0206(4) Uani 1 1 d . . . . .
H7 H 0.5206 0.5815 -0.2138 0.025 Uiso 1 1 calc R . . . .
C8 C 0.5710(3) 0.4065(2) -0.13323(16) 0.0202(4) Uani 1 1 d . . . . .
H8A H 0.6055 0.3238 -0.1520 0.024 Uiso 1 1 calc R . . . .
H8B H 0.6912 0.4252 -0.1078 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7020(4) 0.2461(2) -0.33746(19) 0.0314(5) Uani 1 1 d . . . . .
H9A H 0.8321 0.2619 -0.3676 0.047 Uiso 1 1 calc GR . . . .
H9B H 0.6663 0.1806 -0.3668 0.047 Uiso 1 1 calc GR . . . .
H9C H 0.7107 0.2217 -0.2642 0.047 Uiso 1 1 calc GR . . . .
C10 C 0.6970(3) 0.5415(2) -0.38401(17) 0.0226(5) Uani 1 1 d . . . . .
H10 H 0.7466 0.5157 -0.4467 0.027 Uiso 1 1 calc R . . . .
C11 C 0.7518(3) 0.65640(19) -0.36461(17) 0.0208(4) Uani 1 1 d . . . . .
H11 H 0.7771 0.6470 -0.2913 0.025 Uiso 1 1 calc R . . . .
C12 C 0.9435(3) 0.6789(2) -0.42628(17) 0.0218(5) Uani 1 1 d . . . . .
H12A H 1.0554 0.6101 -0.4068 0.026 Uiso 1 1 calc R . . . .
H12B H 0.9241 0.6828 -0.4990 0.026 Uiso 1 1 calc R . . . .
C13 C 0.9981(3) 0.7960(2) -0.40958(18) 0.0254(5) Uani 1 1 d . . . . .
H13A H 1.1196 0.8094 -0.4527 0.031 Uiso 1 1 calc R . . . .
H13B H 1.0300 0.7891 -0.3382 0.031 Uiso 1 1 calc R . . . .
C14 C 0.8272(3) 0.9042(2) -0.43452(19) 0.0288(5) Uani 1 1 d . . . . .
H14A H 0.8034 0.9160 -0.5074 0.035 Uiso 1 1 calc R . . . .
H14B H 0.8646 0.9788 -0.4197 0.035 Uiso 1 1 calc R . . . .
C15 C 0.6356(4) 0.8831(2) -0.3724(2) 0.0298(5) Uani 1 1 d . . . . .
H15A H 0.6553 0.8797 -0.2999 0.036 Uiso 1 1 calc R . . . .
H15B H 0.5241 0.9520 -0.3922 0.036 Uiso 1 1 calc R . . . .
C16 C 0.5809(3) 0.7657(2) -0.38876(19) 0.0254(5) Uani 1 1 d . . . . .
H16A H 0.5476 0.7727 -0.4600 0.031 Uiso 1 1 calc R . . . .
H16B H 0.4599 0.7523 -0.3452 0.031 Uiso 1 1 calc R . . . .
C17 C 0.2962(3) 0.19669(19) -0.03220(16) 0.0194(4) Uani 1 1 d . . . . .
C18 C 0.0922(3) 0.1994(2) -0.03255(19) 0.0272(5) Uani 1 1 d . . . . .
H18 H -0.0016 0.2518 0.0050 0.033 Uiso 1 1 calc R . . . .
C19 C 0.0276(3) 0.1256(2) -0.0877(2) 0.0329(6) Uani 1 1 d . . . . .
H19 H -0.1123 0.1270 -0.0876 0.039 Uiso 1 1 calc R . . . .
C20 C 0.1605(4) 0.0487(2) -0.14374(19) 0.0281(5) Uani 1 1 d . . . . .
C21 C 0.3629(4) 0.0460(2) -0.14108(18) 0.0255(5) Uani 1 1 d . . . . .
H21 H 0.4567 -0.0067 -0.1783 0.031 Uiso 1 1 calc R . . . .
C22 C 0.4310(3) 0.11832(19) -0.08549(17) 0.0222(5) Uani 1 1 d . . . . .
H22 H 0.5713 0.1145 -0.0836 0.027 Uiso 1 1 calc R . . . .
C23 C 0.0879(4) -0.0305(2) -0.2050(2) 0.0427(7) Uani 1 1 d . . . . .
H23A H -0.0542 -0.0315 -0.1863 0.064 Uiso 1 1 calc GR . . . .
H23B H 0.1669 -0.1134 -0.1918 0.064 Uiso 1 1 calc GR . . . .
H23C H 0.1034 0.0017 -0.2770 0.064 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 1.4311(18) . ?
S1 O2 1.4314(18) . ?
S1 N1 1.605(2) . ?
S1 C17 1.745(2) . ?
N1 C1 1.479(3) . ?
N1 C8 1.483(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.523(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.489(3) . ?
C2 C7 1.542(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.324(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.497(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.511(3) . ?
C5 C9 1.534(3) . ?
C6 C7 1.505(3) . ?
C6 C10 1.322(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.526(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.500(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.527(3) . ?
C11 C16 1.528(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.511(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.524(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.514(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.384(3) . ?
C17 C22 1.381(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.368(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C20 C21 1.376(3) . ?
C20 C23 1.498(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 O2 120.54(11) . . ?
O1 S1 N1 106.36(10) . . ?
O1 S1 C17 107.87(11) . . ?
O2 S1 N1 107.02(10) . . ?
O2 S1 C17 107.41(11) . . ?
N1 S1 C17 106.95(11) . . ?
C1 N1 S1 120.39(15) . . ?
C1 N1 C8 110.62(17) . . ?
C8 N1 S1 119.08(14) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
N1 C1 C2 104.24(17) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C1 C2 H2 110.3 . . ?
C1 C2 C7 102.43(17) . . ?
C3 C2 C1 112.57(19) . . ?
C3 C2 H2 110.3 . . ?
C3 C2 C7 110.74(18) . . ?
C7 C2 H2 110.3 . . ?
C2 C3 H3 117.9 . . ?
C4 C3 C2 124.2(2) . . ?
C4 C3 H3 117.9 . . ?
C3 C4 H4 117.4 . . ?
C3 C4 C5 125.3(2) . . ?
C5 C4 H4 117.4 . . ?
C4 C5 H5 106.3 . . ?
C4 C5 C6 111.46(19) . . ?
C4 C5 C9 111.7(2) . . ?
C6 C5 H5 106.3 . . ?
C6 C5 C9 114.2(2) . . ?
C9 C5 H5 106.3 . . ?
C7 C6 C5 116.69(19) . . ?
C10 C6 C5 120.2(2) . . ?
C10 C6 C7 123.0(2) . . ?
C2 C7 H7 108.7 . . ?
C6 C7 C2 112.60(18) . . ?
C6 C7 H7 108.7 . . ?
C6 C7 C8 114.44(18) . . ?
C8 C7 C2 103.52(17) . . ?
C8 C7 H7 108.7 . . ?
N1 C8 C7 104.21(17) . . ?
N1 C8 H8A 110.9 . . ?
N1 C8 H8B 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10 116.1 . . ?
C6 C10 C11 127.7(2) . . ?
C11 C10 H10 116.1 . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C12 110.76(18) . . ?
C10 C11 C16 111.19(18) . . ?
C12 C11 H11 108.3 . . ?
C12 C11 C16 109.99(18) . . ?
C16 C11 H11 108.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.46(18) . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C12 C13 C14 111.39(19) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C13 C14 H14A 109.6 . . ?
C13 C14 H14B 109.6 . . ?
C13 C14 C15 110.4(2) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 110.90(19) . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C11 C16 H16A 109.2 . . ?
C11 C16 H16B 109.2 . . ?
C15 C16 C11 111.98(19) . . ?
C15 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C18 C17 S1 119.85(17) . . ?
C22 C17 S1 120.15(17) . . ?
C22 C17 C18 119.8(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.0(2) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.9(2) . . ?
C20 C19 H19 119.1 . . ?
C19 C20 C23 121.4(2) . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 C23 120.4(2) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 120.9(2) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 119.9 . . ?
C21 C22 C17 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 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
S1 N1 C1 C2 -129.38(16) . . . . ?
S1 N1 C8 C7 154.29(14) . . . . ?
S1 C17 C18 C19 174.0(2) . . . . ?
S1 C17 C22 C21 -173.27(18) . . . . ?
O1 S1 N1 C1 -177.04(15) . . . . ?
O1 S1 N1 C8 40.47(17) . . . . ?
O1 S1 C17 C18 153.92(19) . . . . ?
O1 S1 C17 C22 -30.8(2) . . . . ?
O2 S1 N1 C1 -46.98(18) . . . . ?
O2 S1 N1 C8 170.54(15) . . . . ?
O2 S1 C17 C18 22.6(2) . . . . ?
O2 S1 C17 C22 -162.19(18) . . . . ?
N1 S1 C17 C18 -92.0(2) . . . . ?
N1 S1 C17 C22 83.2(2) . . . . ?
N1 C1 C2 C3 85.6(2) . . . . ?
N1 C1 C2 C7 -33.4(2) . . . . ?
C1 N1 C8 C7 8.4(2) . . . . ?
C1 C2 C3 C4 -131.8(2) . . . . ?
C1 C2 C7 C6 162.84(18) . . . . ?
C1 C2 C7 C8 38.7(2) . . . . ?
C2 C3 C4 C5 -2.2(4) . . . . ?
C2 C7 C8 N1 -29.1(2) . . . . ?
C3 C2 C7 C6 42.6(2) . . . . ?
C3 C2 C7 C8 -81.5(2) . . . . ?
C3 C4 C5 C6 -3.4(3) . . . . ?
C3 C4 C5 C9 125.6(3) . . . . ?
C4 C5 C6 C7 30.5(3) . . . . ?
C4 C5 C6 C10 -145.8(2) . . . . ?
C5 C6 C7 C2 -51.4(3) . . . . ?
C5 C6 C7 C8 66.5(3) . . . . ?
C5 C6 C10 C11 177.3(2) . . . . ?
C6 C7 C8 N1 -152.00(17) . . . . ?
C6 C10 C11 C12 155.8(2) . . . . ?
C6 C10 C11 C16 -81.6(3) . . . . ?
C7 C2 C3 C4 -17.8(3) . . . . ?
C7 C6 C10 C11 1.2(4) . . . . ?
C8 N1 C1 C2 16.0(2) . . . . ?
C9 C5 C6 C7 -97.2(2) . . . . ?
C9 C5 C6 C10 86.5(3) . . . . ?
C10 C6 C7 C2 124.8(2) . . . . ?
C10 C6 C7 C8 -117.3(2) . . . . ?
C10 C11 C12 C13 178.59(18) . . . . ?
C10 C11 C16 C15 -178.39(19) . . . . ?
C11 C12 C13 C14 -56.7(3) . . . . ?
C12 C11 C16 C15 -55.3(3) . . . . ?
C12 C13 C14 C15 56.5(3) . . . . ?
C13 C14 C15 C16 -56.0(3) . . . . ?
C14 C15 C16 C11 56.2(3) . . . . ?
C16 C11 C12 C13 55.3(2) . . . . ?
C17 S1 N1 C1 67.89(18) . . . . ?
C17 S1 N1 C8 -74.60(17) . . . . ?
C17 C18 C19 C20 -0.4(4) . . . . ?
C18 C17 C22 C21 2.0(3) . . . . ?
C18 C19 C20 C21 1.4(4) . . . . ?
C18 C19 C20 C23 -179.2(3) . . . . ?
C19 C20 C21 C22 -0.7(4) . . . . ?
C20 C21 C22 C17 -0.9(4) . . . . ?
C22 C17 C18 C19 -1.3(4) . . . . ?
C23 C20 C21 C22 179.8(2) . . . . ?

_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_cd17234
_database_code_depnum_ccdc_archive 'CCDC 1555722'
_audit_update_record             
;
2017-06-13 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H23 N O2 S'
_chemical_formula_weight         317.43

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6868(14)
_cell_length_b                   20.200(3)
_cell_length_c                   8.0112(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.747(3)
_cell_angle_gamma                90
_cell_volume                     1693.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2189
_cell_measurement_theta_min      4.384
_cell_measurement_theta_max      46.042

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.198
_shelx_estimated_absorpt_T_min   0.961
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9268
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.946
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             2981
_reflns_number_gt                2365
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0661P)²+0.4888P] 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         2981
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_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 0.78534(5) 1.01257(3) 0.70330(7) 0.0451(2) Uani 1 1 d . . . . .
N1 N 0.67970(17) 0.97160(9) 0.7803(2) 0.0446(5) Uani 1 1 d . . . . .
O1 O 0.85365(16) 1.05261(8) 0.8383(2) 0.0570(5) Uani 1 1 d . . . . .
O2 O 0.71795(15) 1.04282(8) 0.5508(2) 0.0586(5) Uani 1 1 d . . . . .
C1 C 0.5947(2) 0.92657(13) 0.6626(3) 0.0525(6) Uani 1 1 d . . . . .
H1A H 0.6403 0.9057 0.5836 0.063 Uiso 1 1 calc R U . . .
H1B H 0.5217 0.9503 0.5982 0.063 Uiso 1 1 calc R U . . .
C2 C 0.7121(2) 0.94247(11) 0.9529(3) 0.0481(6) Uani 1 1 d . . . . .
H2A H 0.6678 0.9654 1.0302 0.058 Uiso 1 1 calc R U . . .
H2B H 0.8034 0.9447 0.9980 0.058 Uiso 1 1 calc R U . . .
C3 C 0.6677(2) 0.87084(10) 0.9282(3) 0.0400(5) Uani 1 1 d . . . . .
H3 H 0.7348 0.8449 0.8915 0.048 Uiso 1 1 calc R U . . .
C4 C 0.5529(2) 0.87558(11) 0.7795(3) 0.0436(5) Uani 1 1 d . . . . .
H4 H 0.5397 0.8328 0.7208 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4348(2) 0.89460(12) 0.8389(3) 0.0525(6) Uani 1 1 d . . . . .
H5 H 0.3652 0.9093 0.7580 0.063 Uiso 1 1 calc R U . . .
C6 C 0.4229(2) 0.89186(12) 0.9982(3) 0.0558(6) Uani 1 1 d . . . . .
H6 H 0.3452 0.9052 1.0222 0.067 Uiso 1 1 calc R U . . .
C7 C 0.5237(2) 0.86912(11) 1.1450(3) 0.0485(6) Uani 1 1 d . . . . .
H7 H 0.5556 0.9088 1.2105 0.058 Uiso 1 1 calc R U . . .
C8 C 0.6369(2) 0.83895(10) 1.0849(3) 0.0394(5) Uani 1 1 d . . . . .
C9 C 0.7027(2) 0.78875(11) 1.1641(3) 0.0493(6) Uani 1 1 d . . . . .
H9 H 0.6736 0.7720 1.2574 0.059 Uiso 1 1 calc R U . . .
C10 C 0.8178(3) 0.75535(13) 1.1236(3) 0.0650(7) Uani 1 1 d . . . . .
H10A H 0.7937 0.7131 1.0720 0.098 Uiso 1 1 calc R U . . .
H10B H 0.8805 0.7491 1.2267 0.098 Uiso 1 1 calc R U . . .
H10C H 0.8532 0.7824 1.0462 0.098 Uiso 1 1 calc R U . . .
C11 C 0.4645(3) 0.82531(15) 1.2630(4) 0.0732(8) Uani 1 1 d . . . . .
H11A H 0.3959 0.8487 1.2978 0.110 Uiso 1 1 calc R U . . .
H11B H 0.5283 0.8141 1.3616 0.110 Uiso 1 1 calc R U . . .
H11C H 0.4320 0.7856 1.2038 0.110 Uiso 1 1 calc R U . . .
C12 C 0.8924(2) 0.95471(11) 0.6458(3) 0.0462(5) Uani 1 1 d . . . . .
C13 C 0.9881(2) 0.92823(13) 0.7698(3) 0.0577(6) Uani 1 1 d . . . . .
H13 H 0.9985 0.9421 0.8825 0.069 Uiso 1 1 calc R U . . .
C14 C 1.0683(2) 0.88083(14) 0.7243(4) 0.0704(8) Uani 1 1 d . . . . .
H14 H 1.1321 0.8625 0.8079 0.084 Uiso 1 1 calc R U . . .
C15 C 1.0559(3) 0.86012(13) 0.5573(5) 0.0692(8) Uani 1 1 d . . . . .
C16 C 0.9609(3) 0.88832(13) 0.4364(4) 0.0651(7) Uani 1 1 d . . . . .
H16 H 0.9519 0.8755 0.3231 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8789(2) 0.93490(13) 0.4783(3) 0.0543(6) Uani 1 1 d . . . . .
H17 H 0.8149 0.9529 0.3945 0.065 Uiso 1 1 calc R U . . .
C18 C 1.1447(3) 0.80854(17) 0.5100(6) 0.1063(13) Uani 1 1 d . . . . .
H18A H 1.1093 0.7653 0.5189 0.159 Uiso 1 1 calc R U . . .
H18B H 1.2264 0.8116 0.5861 0.159 Uiso 1 1 calc R U . . .
H18C H 1.1547 0.8159 0.3951 0.159 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
S1 O2 1.4236(16) . ?
S1 O1 1.4266(16) . ?
S1 N1 1.6197(18) . ?
S1 C12 1.761(2) . ?
N1 C2 1.478(3) . ?
N1 C1 1.481(3) . ?
C1 C4 1.519(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.523(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.506(3) . ?
C3 C4 1.529(3) . ?
C3 H3 0.9800 . ?
C4 C5 1.487(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.309(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.496(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.518(3) . ?
C7 C11 1.523(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.321(3) . ?
C9 C10 1.496(3) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C17 1.380(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.383(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.382(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.376(4) . ?
C15 C18 1.508(4) . ?
C16 C17 1.373(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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 119.91(10) . . ?
O2 S1 N1 106.03(9) . . ?
O1 S1 N1 106.84(10) . . ?
O2 S1 C12 107.62(11) . . ?
O1 S1 C12 108.37(10) . . ?
N1 S1 C12 107.49(10) . . ?
C2 N1 C1 110.35(17) . . ?
C2 N1 S1 120.75(14) . . ?
C1 N1 S1 117.13(15) . . ?
N1 C1 C4 104.06(17) . . ?
N1 C1 H1A 110.9 . . ?
C4 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
C4 C1 H1B 110.9 . . ?
H1A C1 H1B 109.0 . . ?
N1 C2 C3 104.45(17) . . ?
N1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
N1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C8 C3 C2 114.42(17) . . ?
C8 C3 C4 113.52(18) . . ?
C2 C3 C4 102.75(17) . . ?
C8 C3 H3 108.6 . . ?
C2 C3 H3 108.6 . . ?
C4 C3 H3 108.6 . . ?
C5 C4 C1 113.4(2) . . ?
C5 C4 C3 111.44(18) . . ?
C1 C4 C3 103.46(17) . . ?
C5 C4 H4 109.4 . . ?
C1 C4 H4 109.4 . . ?
C3 C4 H4 109.4 . . ?
C6 C5 C4 123.9(2) . . ?
C6 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C5 C6 C7 125.6(2) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C6 C7 C8 111.48(19) . . ?
C6 C7 C11 110.0(2) . . ?
C8 C7 C11 115.0(2) . . ?
C6 C7 H7 106.6 . . ?
C8 C7 H7 106.6 . . ?
C11 C7 H7 106.6 . . ?
C9 C8 C3 122.9(2) . . ?
C9 C8 C7 122.5(2) . . ?
C3 C8 C7 114.62(17) . . ?
C8 C9 C10 128.6(2) . . ?
C8 C9 H9 115.7 . . ?
C10 C9 H9 115.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C12 C13 120.2(2) . . ?
C17 C12 S1 120.16(18) . . ?
C13 C12 S1 119.66(19) . . ?
C12 C13 C14 119.1(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 117.9(3) . . ?
C16 C15 C18 121.4(3) . . ?
C14 C15 C18 120.7(3) . . ?
C17 C16 C15 121.8(3) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C12 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C12 C17 H17 120.3 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 N1 C2 -170.28(17) . . . . ?
O1 S1 N1 C2 -41.3(2) . . . . ?
C12 S1 N1 C2 74.85(19) . . . . ?
O2 S1 N1 C1 50.30(19) . . . . ?
O1 S1 N1 C1 179.28(16) . . . . ?
C12 S1 N1 C1 -64.58(18) . . . . ?
C2 N1 C1 C4 12.1(2) . . . . ?
S1 N1 C1 C4 155.51(16) . . . . ?
C1 N1 C2 C3 12.2(2) . . . . ?
S1 N1 C2 C3 -129.66(17) . . . . ?
N1 C2 C3 C8 -154.82(18) . . . . ?
N1 C2 C3 C4 -31.3(2) . . . . ?
N1 C1 C4 C5 89.5(2) . . . . ?
N1 C1 C4 C3 -31.4(2) . . . . ?
C8 C3 C4 C5 40.8(3) . . . . ?
C2 C3 C4 C5 -83.3(2) . . . . ?
C8 C3 C4 C1 163.00(18) . . . . ?
C2 C3 C4 C1 38.9(2) . . . . ?
C1 C4 C5 C6 -131.7(3) . . . . ?
C3 C4 C5 C6 -15.5(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C5 C6 C7 C8 -8.9(3) . . . . ?
C5 C6 C7 C11 -137.7(3) . . . . ?
C2 C3 C8 C9 -114.8(2) . . . . ?
C4 C3 C8 C9 127.6(2) . . . . ?
C2 C3 C8 C7 65.2(2) . . . . ?
C4 C3 C8 C7 -52.4(2) . . . . ?
C6 C7 C8 C9 -145.2(2) . . . . ?
C11 C7 C8 C9 -19.1(3) . . . . ?
C6 C7 C8 C3 34.8(3) . . . . ?
C11 C7 C8 C3 160.9(2) . . . . ?
C3 C8 C9 C10 2.0(4) . . . . ?
C7 C8 C9 C10 -178.0(2) . . . . ?
O2 S1 C12 C17 -14.8(2) . . . . ?
O1 S1 C12 C17 -145.89(18) . . . . ?
N1 S1 C12 C17 99.0(2) . . . . ?
O2 S1 C12 C13 166.53(18) . . . . ?
O1 S1 C12 C13 35.5(2) . . . . ?
N1 S1 C12 C13 -79.66(19) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
S1 C12 C13 C14 177.38(19) . . . . ?
C12 C13 C14 C15 0.9(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C13 C14 C15 C18 179.8(3) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C18 C15 C16 C17 179.4(2) . . . . ?
C15 C16 C17 C12 0.6(4) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
S1 C12 C17 C16 -178.12(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13 O1 0.93 2.46 3.272(3) 145.3 3_777
C1 H1B O2 0.97 2.60 3.485(3) 151.8 3_676
C1 H1B O2 0.97 2.60 3.485(3) 151.8 3_676
C13 H13 O1 0.93 2.46 3.272(3) 145.3 3_777

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.201
_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_mo_dm16454_0m
_database_code_depnum_ccdc_archive 'CCDC 1555723'
_audit_update_record             
;
2017-09-18 deposited with the CCDC.
2018-07-30 downloaded from the CCDC.
;
_audit_creation_date             2016-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H30 O4'
_chemical_formula_sum            'C24 H30 O4'
_chemical_formula_weight         382.48
_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 0.0030 0.0020 '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 0.0110 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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9632(10)
_cell_length_b                   26.894(3)
_cell_length_c                   9.2793(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.151(2)
_cell_angle_gamma                90
_cell_volume                     2099.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5442
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.64
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6211
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0626 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.8325.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21185
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.925
_diffrn_reflns_theta_min         2.420
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_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                4462
_reflns_number_total             6552
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.352
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         6552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.013
_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)+(0.0506P)²+0.4595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1227
_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:
 C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C)
;
_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
O1 O -0.64093(11) -0.10125(3) 0.82782(12) 0.0353(2) Uani 1 1 d . . . . .
O2 O -0.45596(13) -0.04800(4) 0.81133(14) 0.0447(3) Uani 1 1 d . . . . .
O3 O -0.36269(12) -0.16102(3) 0.99982(11) 0.0353(2) Uani 1 1 d . . . . .
O4 O -0.45604(16) -0.22023(4) 0.82361(13) 0.0536(3) Uani 1 1 d . . . . .
C1 C -0.50939(15) -0.08933(5) 0.79818(15) 0.0272(3) Uani 1 1 d . . . . .
C2 C -0.44343(14) -0.13486(4) 0.74199(14) 0.0251(2) Uani 1 1 d . . . . .
C3 C -0.42544(15) -0.17733(5) 0.85582(15) 0.0285(3) Uani 1 1 d . . . . .
C4 C -0.3343(2) -0.19791(5) 1.11965(17) 0.0420(4) Uani 1 1 d . . . . .
H4A H -0.4350 -0.2138 1.1126 0.063 Uiso 1 1 calc GR . . . .
H4B H -0.2881 -0.1818 1.2201 0.063 Uiso 1 1 calc GR . . . .
H4C H -0.2605 -0.2231 1.1076 0.063 Uiso 1 1 calc GR . . . .
C5 C -0.27843(14) -0.12381(5) 0.72757(14) 0.0263(2) Uani 1 1 d . . . . .
H5A H -0.2630 -0.0876 0.7194 0.032 Uiso 1 1 calc R . . . .
H5B H -0.1914 -0.1369 0.8175 0.032 Uiso 1 1 calc R . . . .
C6 C -0.28320(13) -0.15073(4) 0.57964(14) 0.0234(2) Uani 1 1 d . . . . .
H6 H -0.2699 -0.1872 0.6021 0.028 Uiso 1 1 calc R . . . .
C7 C -0.45479(14) -0.14172(5) 0.47270(15) 0.0261(2) Uani 1 1 d . . . . .
H7 H -0.4848 -0.1665 0.3871 0.031 Uiso 1 1 calc R . . . .
C8 C -0.55291(15) -0.15049(5) 0.57730(15) 0.0297(3) Uani 1 1 d . . . . .
H8A H -0.5832 -0.1859 0.5756 0.036 Uiso 1 1 calc R . . . .
H8B H -0.6508 -0.1301 0.5433 0.036 Uiso 1 1 calc R . . . .
C9 C -0.47599(14) -0.08898(5) 0.40784(16) 0.0301(3) Uani 1 1 d . . . . .
H9A H -0.5779 -0.0870 0.3209 0.036 Uiso 1 1 calc R . . . .
H9B H -0.4819 -0.0656 0.4881 0.036 Uiso 1 1 calc R . . . .
C10 C -0.34428(14) -0.07323(5) 0.35376(15) 0.0271(3) Uani 1 1 d . . . . .
H10 H -0.3653 -0.0475 0.2793 0.032 Uiso 1 1 calc R . . . .
C11 C -0.19772(14) -0.09324(4) 0.40390(14) 0.0232(2) Uani 1 1 d . . . . .
C12 C -0.15613(14) -0.13454(4) 0.51604(13) 0.0227(2) Uani 1 1 d . . . . .
C13 C -0.01418(14) -0.15735(4) 0.55547(15) 0.0267(3) Uani 1 1 d . . . . .
H13 H 0.0573 -0.1448 0.5089 0.032 Uiso 1 1 calc R . . . .
C14 C 0.04550(15) -0.20015(5) 0.66362(15) 0.0292(3) Uani 1 1 d . . . . .
H14A H -0.0338 -0.2083 0.7124 0.035 Uiso 1 1 calc R . . . .
H14B H 0.1453 -0.1903 0.7457 0.035 Uiso 1 1 calc R . . . .
C15 C 0.07617(16) -0.24613(5) 0.58176(16) 0.0312(3) Uani 1 1 d . . . . .
H15A H 0.1498 -0.2371 0.5272 0.037 Uiso 1 1 calc R . . . .
H15B H -0.0253 -0.2568 0.5038 0.037 Uiso 1 1 calc R . . . .
C16 C 0.14659(18) -0.28976(5) 0.68880(17) 0.0387(3) Uani 1 1 d . . . . .
H16A H 0.2457 -0.2788 0.7698 0.046 Uiso 1 1 calc R . . . .
H16B H 0.0708 -0.3001 0.7394 0.046 Uiso 1 1 calc R . . . .
C17 C 0.1829(2) -0.33391(6) 0.6050(2) 0.0514(4) Uani 1 1 d . . . . .
H17A H 0.0861 -0.3440 0.5217 0.077 Uiso 1 1 calc GR . . . .
H17B H 0.2211 -0.3616 0.6769 0.077 Uiso 1 1 calc GR . . . .
H17C H 0.2648 -0.3247 0.5621 0.077 Uiso 1 1 calc GR . . . .
C18 C -0.07656(14) -0.07205(4) 0.34367(14) 0.0234(2) Uani 1 1 d . . . . .
C19 C 0.06401(15) -0.05079(5) 0.44176(16) 0.0290(3) Uani 1 1 d . . . . .
H19 H 0.0879 -0.0522 0.5497 0.035 Uiso 1 1 calc R . . . .
C20 C 0.16906(15) -0.02757(5) 0.38312(18) 0.0338(3) Uani 1 1 d . . . . .
H20 H 0.2634 -0.0128 0.4511 0.041 Uiso 1 1 calc R . . . .
C21 C 0.13741(17) -0.02573(5) 0.22646(18) 0.0352(3) Uani 1 1 d . . . . .
H21 H 0.2095 -0.0098 0.1867 0.042 Uiso 1 1 calc R . . . .
C22 C -0.00013(17) -0.04732(5) 0.12811(17) 0.0349(3) Uani 1 1 d . . . . .
H22 H -0.0217 -0.0466 0.0204 0.042 Uiso 1 1 calc R . . . .
C23 C -0.10705(16) -0.07009(5) 0.18626(15) 0.0290(3) Uani 1 1 d . . . . .
H23 H -0.2018 -0.0844 0.1177 0.035 Uiso 1 1 calc R . . . .
C24 C -0.7114(2) -0.06148(6) 0.8883(2) 0.0438(4) Uani 1 1 d . . . . .
H24A H -0.7375 -0.0336 0.8160 0.066 Uiso 1 1 calc GR . . . .
H24B H -0.6359 -0.0504 0.9872 0.066 Uiso 1 1 calc GR . . . .
H24C H -0.8086 -0.0736 0.9025 0.066 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
O1 C1 1.3386(15) . ?
O1 C24 1.4498(17) . ?
O2 C1 1.1998(15) . ?
O3 C3 1.3327(16) . ?
O3 C4 1.4457(16) . ?
O4 C3 1.1998(16) . ?
C1 C2 1.5275(17) . ?
C2 C3 1.5260(18) . ?
C2 C5 1.5588(17) . ?
C2 C8 1.5627(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5394(17) . ?
C6 H6 1.0000 . ?
C6 C7 1.5353(17) . ?
C6 C12 1.5160(16) . ?
C7 H7 1.0000 . ?
C7 C8 1.5361(17) . ?
C7 C9 1.5268(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4943(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3456(16) . ?
C11 C12 1.4792(16) . ?
C11 C18 1.4948(16) . ?
C12 C13 1.3448(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.4995(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5250(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5263(18) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.515(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.3975(17) . ?
C18 C23 1.3914(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.3876(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.3932(18) . ?
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
C1 O1 C24 115.78(11) . . ?
C3 O3 C4 116.56(10) . . ?
O1 C1 C2 110.49(10) . . ?
O2 C1 O1 123.36(12) . . ?
O2 C1 C2 126.12(12) . . ?
C1 C2 C5 111.51(10) . . ?
C1 C2 C8 111.28(10) . . ?
C3 C2 C1 108.95(10) . . ?
C3 C2 C5 108.97(10) . . ?
C3 C2 C8 110.89(10) . . ?
C5 C2 C8 105.19(10) . . ?
O3 C3 C2 110.80(10) . . ?
O4 C3 O3 123.20(13) . . ?
O4 C3 C2 125.92(12) . . ?
O3 C4 H4A 109.5 . . ?
O3 C4 H4B 109.5 . . ?
O3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 110.8 . . ?
C2 C5 H5B 110.8 . . ?
H5A C5 H5B 108.9 . . ?
C6 C5 C2 104.54(9) . . ?
C6 C5 H5A 110.8 . . ?
C6 C5 H5B 110.8 . . ?
C5 C6 H6 108.1 . . ?
C7 C6 C5 102.48(9) . . ?
C7 C6 H6 108.1 . . ?
C12 C6 C5 114.72(10) . . ?
C12 C6 H6 108.1 . . ?
C12 C6 C7 115.00(10) . . ?
C6 C7 H7 110.1 . . ?
C6 C7 C8 103.38(10) . . ?
C8 C7 H7 110.1 . . ?
C9 C7 C6 111.25(10) . . ?
C9 C7 H7 110.1 . . ?
C9 C7 C8 111.79(10) . . ?
C2 C8 H8A 110.6 . . ?
C2 C8 H8B 110.6 . . ?
C7 C8 C2 105.86(9) . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C7 C9 H9A 109.0 . . ?
C7 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C7 112.96(10) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10 117.9 . . ?
C11 C10 C9 124.10(11) . . ?
C11 C10 H10 117.9 . . ?
C10 C11 C12 121.53(11) . . ?
C10 C11 C18 117.82(11) . . ?
C12 C11 C18 120.65(10) . . ?
C11 C12 C6 116.65(10) . . ?
C13 C12 C6 122.03(11) . . ?
C13 C12 C11 121.29(11) . . ?
C12 C13 H13 115.9 . . ?
C12 C13 C14 128.19(12) . . ?
C14 C13 H13 115.9 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C13 C14 C15 111.91(11) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C14 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C14 C15 C16 113.85(11) . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 C15 112.47(13) . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C11 121.37(11) . . ?
C23 C18 C11 120.11(11) . . ?
C23 C18 C19 118.37(11) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.67(13) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.48(13) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.46(12) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.29(13) . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.71(12) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O1 C24 H24A 109.5 . . ?
O1 C24 H24B 109.5 . . ?
O1 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O1 C1 C2 C3 -52.07(13) . . . . ?
O1 C1 C2 C5 -172.38(10) . . . . ?
O1 C1 C2 C8 70.50(13) . . . . ?
O2 C1 C2 C3 129.73(15) . . . . ?
O2 C1 C2 C5 9.42(19) . . . . ?
O2 C1 C2 C8 -107.70(15) . . . . ?
C1 C2 C3 O3 -43.43(14) . . . . ?
C1 C2 C3 O4 139.61(14) . . . . ?
C1 C2 C5 C6 -140.43(10) . . . . ?
C1 C2 C8 C7 114.14(11) . . . . ?
C2 C5 C6 C7 38.72(12) . . . . ?
C2 C5 C6 C12 164.06(10) . . . . ?
C3 C2 C5 C6 99.27(11) . . . . ?
C3 C2 C8 C7 -124.42(11) . . . . ?
C4 O3 C3 O4 -1.0(2) . . . . ?
C4 O3 C3 C2 -178.05(11) . . . . ?
C5 C2 C3 O3 78.43(12) . . . . ?
C5 C2 C3 O4 -98.52(16) . . . . ?
C5 C2 C8 C7 -6.76(13) . . . . ?
C5 C6 C7 C8 -42.97(12) . . . . ?
C5 C6 C7 C9 77.16(12) . . . . ?
C5 C6 C12 C11 -90.66(13) . . . . ?
C5 C6 C12 C13 91.27(14) . . . . ?
C6 C7 C8 C2 30.71(12) . . . . ?
C6 C7 C9 C10 44.61(15) . . . . ?
C6 C12 C13 C14 -0.6(2) . . . . ?
C7 C6 C12 C11 27.84(14) . . . . ?
C7 C6 C12 C13 -150.23(12) . . . . ?
C7 C9 C10 C11 -23.22(18) . . . . ?
C8 C2 C3 O3 -166.24(10) . . . . ?
C8 C2 C3 O4 16.80(19) . . . . ?
C8 C2 C5 C6 -19.68(12) . . . . ?
C8 C7 C9 C10 159.62(11) . . . . ?
C9 C7 C8 C2 -89.04(12) . . . . ?
C9 C10 C11 C12 1.93(19) . . . . ?
C9 C10 C11 C18 -177.51(11) . . . . ?
C10 C11 C12 C6 -4.08(17) . . . . ?
C10 C11 C12 C13 174.01(12) . . . . ?
C10 C11 C18 C19 119.55(13) . . . . ?
C10 C11 C18 C23 -56.02(16) . . . . ?
C11 C12 C13 C14 -178.54(12) . . . . ?
C11 C18 C19 C20 -174.57(11) . . . . ?
C11 C18 C23 C22 175.49(11) . . . . ?
C12 C6 C7 C8 -168.12(10) . . . . ?
C12 C6 C7 C9 -48.00(14) . . . . ?
C12 C11 C18 C19 -59.90(16) . . . . ?
C12 C11 C18 C23 124.53(12) . . . . ?
C12 C13 C14 C15 116.00(15) . . . . ?
C13 C14 C15 C16 176.51(11) . . . . ?
C14 C15 C16 C17 -177.25(13) . . . . ?
C18 C11 C12 C6 175.35(10) . . . . ?
C18 C11 C12 C13 -6.57(17) . . . . ?
C18 C19 C20 C21 -0.94(19) . . . . ?
C19 C18 C23 C22 -0.21(18) . . . . ?
C19 C20 C21 C22 -0.1(2) . . . . ?
C20 C21 C22 C23 1.0(2) . . . . ?
C21 C22 C23 C18 -0.8(2) . . . . ?
C23 C18 C19 C20 1.08(18) . . . . ?
C24 O1 C1 O2 -4.2(2) . . . . ?
C24 O1 C1 C2 177.54(11) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
