# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_zhangy_0626
_database_code_depnum_ccdc_archive 'CCDC 1962272'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-06-28
_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         'C22 H28 O5 S'
_chemical_formula_sum            'C22 H28 O5 S'
_chemical_formula_weight         404.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   7.3975(3)
_cell_length_b                   10.7485(5)
_cell_length_c                   13.1441(5)
_cell_angle_alpha                92.571(3)
_cell_angle_beta                 96.250(4)
_cell_angle_gamma                97.449(4)
_cell_volume                     1028.29(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5801
_cell_measurement_temperature    292.1(3)
_cell_measurement_theta_max      69.8890
_cell_measurement_theta_min      6.7770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         4.156
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.1(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     44.00 116.00   1.00    1.50    --  108.00-111.00 150.00   72
  2  ω     41.00  95.00   1.00    1.50    --  108.00 -63.00 150.00   54
  3  ω     43.00  72.00   1.00    1.00    --   64.00  42.00 130.49   29
  4  ω     67.00  98.00   1.00    1.50    --   84.00  46.00 157.56   31
  5  ω     86.00 112.00   1.00    1.50    --  108.00  63.00 150.00   26
  6  ω    112.00 168.00   1.00    1.50    --  108.00  77.00 120.00   56
  7  ω     98.00 125.00   1.00    1.00    --   60.00  76.00  40.65   27
  8  ω     83.00 114.00   1.00    1.50    --  104.00  60.00  -4.43   31
  9  ω    113.00 169.00   1.00    1.50    --  108.00  77.00 -30.00   56
 10  ω    116.00 177.00   1.00    1.50    --  108.00  77.00 -90.00   61
 11  ω    102.00 151.00   1.00    1.50    --  108.00 178.00   0.00   49
 12  ω     79.00 176.00   1.00    1.50    --  108.00  77.00   0.00   97
 13  ω     84.00 130.00   1.00    1.00    --   64.00  66.00-124.42   46
 14  ω     87.00 112.00   1.00    1.50    --  108.00  63.00-150.00   25
 15  ω     78.00 168.00   1.00    1.50    --  108.00  77.00-150.00   90
 16  ω     83.00 110.00   1.00    1.50    --  108.00  38.00   0.00   27
 17  ω     78.00 160.00   1.00    1.50    --  108.00  77.00 -60.00   82
 18  ω     87.00 112.00   1.00    1.50    --  108.00  63.00  60.00   25
 19  ω     79.00 177.00   1.00    1.50    --  108.00  77.00  30.00   98
 20  ω     86.00 112.00   1.00    1.50    --  108.00  63.00 -60.00   26
 21  ω     78.00 104.00   1.00    1.50    --  108.00  77.00 -30.00   26
 22  ω     78.00 113.00   1.00    1.50    --  108.00  77.00 -90.00   35
 23  ω     79.00 160.00   1.00    1.50    --  108.00  77.00-120.00   81
 24  ω     81.00 177.00   1.00    1.50    --  108.00  77.00-180.00   96
 25  ω     59.00  92.00   1.00    1.50    --   88.00  75.00-163.19   33
 26  ω     54.00 103.00   1.00    1.00    --   80.00  72.00 -92.70   49
 27  ω     51.00 106.00   1.00    1.00    --   72.00  55.00  -3.17   55
 28  ω     71.00 100.00   1.00    1.50    --   92.00  54.00  56.73   29
 29  ω     78.00 154.00   1.00    1.50    --  108.00  77.00  60.00   76
 30  ω     78.00 176.00   1.00    1.50    --  108.00  77.00 150.00   98
 31  ω     79.00 107.00   1.00    1.50    --  108.00  77.00 120.00   28
 32  ω     80.00 166.00   1.00    1.50    --  108.00  77.00  90.00   86
 33  ω     67.00  93.00   1.00    1.50    --   88.00  51.00 129.95   26
 34  ω     48.00  75.00   1.00    1.00    --   68.00  55.00 138.24   27
 35  ω     49.00 140.00   1.00    1.00    --   72.00  66.00 164.20   91
 36  ω     41.00  68.00   1.00    1.00    --    0.00  19.00 -30.00   27
 37  ω     17.00  44.00   1.00    1.00    --   48.00  78.00-115.08   27
 38  ω     41.00  79.00   1.00    1.00    --   64.00  66.00-124.42   38
 39  ω     48.00 113.00   1.00    1.00    --   76.00  77.00 -72.18   65
 40  ω     47.00 133.00   1.00    1.00    --   68.00  63.00  23.94   86
 41  ω     43.00 130.00   1.00    1.00    --   72.00  75.00-110.92   87
 42  ω     45.00  70.00   1.00    1.00    --    0.00  38.00-180.00   25
 43  ω     24.00  50.00   1.00    1.00    --   54.00  77.00-150.00   26
 44  ω     37.00  62.00   1.00    1.00    --   60.00  67.00-174.60   25
 45  ω     28.00  74.00   1.00    1.00    --   56.00  73.00-131.03   46
 46  ω     20.00  45.00   1.00    1.00    --   52.00  81.00 -38.20   25
 47  ω     24.00  50.00   1.00    1.00    --   54.00  77.00   0.00   26
 48  ω     31.00  66.00   1.00    1.00    --   60.00  76.00  40.65   35
 49  ω     27.00  66.00   1.00    1.00    --   54.00  77.00  60.00   39
 50  ω     38.00  64.00   1.00    1.00    --   60.00  62.00 118.01   26
 51  ω     15.00  43.00   1.00    1.00    --   48.00  82.00 153.27   28
 52  ω      9.00  34.00   1.00    1.00    --   44.00  85.00  96.32   25
 53  ω      5.00  30.00   1.00    1.00    --   40.00  85.00  65.41   25
 54  ω      2.00  40.00   1.00    1.00    --    0.00  19.00 -30.00   38
 55  ω     43.00 138.00   1.00    1.50    --  108.00 -77.00 -30.00   95
 56  ω     53.00  89.00   1.00    1.50    --  108.00-111.00-180.00   36
 57  ω     28.00  87.00   1.00    1.00    --   54.00-125.00 -90.00   59
 58  ω     36.00 116.00   1.00    1.50    --  108.00-111.00 -30.00   80
 59  ω      6.00  85.00   1.00    1.00    --   54.00 -99.00  60.00   79
 60  ω    -14.00  74.00   1.00    1.00    --   54.00 -57.00 -90.00   88
 61  ω    -20.00  30.00   1.00    1.00    --    0.00  38.00-180.00   50
 62  ω      7.00  33.00   1.00    1.00    --   44.00  89.00 -77.24   26
 63  ω     25.00  51.00   1.00    1.00    --   54.00  77.00 -60.00   26
 64  ω    -28.00  -3.00   1.00    1.00    --    0.00  19.00 -30.00   25
 65  ω    -24.00   4.00   1.00    1.00    --   24.00 111.00  68.59   28
 66  ω    -19.00  43.00   1.00    1.00    --    0.00 -19.00 120.00   62
 67  ω     -8.00  72.00   1.00    1.00    --   54.00 -57.00 120.00   80
 68  ω    -24.00   1.00   1.00    1.00    --   28.00 117.00-130.18   25
 69  ω    -62.00 -33.00   1.00    1.00    --    0.00 -19.00 120.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0698395000
_diffrn_orient_matrix_UB_12      0.1028010000
_diffrn_orient_matrix_UB_13      -0.0658448000
_diffrn_orient_matrix_UB_21      0.0336692000
_diffrn_orient_matrix_UB_22      -0.0739443000
_diffrn_orient_matrix_UB_23      -0.0977321000
_diffrn_orient_matrix_UB_31      -0.1967211000
_diffrn_orient_matrix_UB_32      -0.0702378000
_diffrn_orient_matrix_UB_33      -0.0080497000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3088
_reflns_number_total             3632
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.047
_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)+(0.0634P)²+0.2953P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1155
_refine_ls_wR_factor_ref         0.1223
_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)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C10(H10A,
 H10B), C11(H11A,H11B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.26333(7) 0.33623(4) 0.91508(3) 0.04391(17) Uani 1 1 d . . . . .
O1 O -0.1622(3) 0.87047(19) 0.61252(13) 0.0920(7) Uani 1 1 d . . . . .
O2 O -0.0575(2) 0.63465(15) 0.44756(10) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.3165(2) 0.48230(13) 0.92510(10) 0.0529(4) Uani 1 1 d . . . . .
O4 O 0.0715(2) 0.30530(18) 0.88719(13) 0.0680(5) Uani 1 1 d . . . . .
O5 O 0.3435(2) 0.29585(14) 1.00921(10) 0.0553(4) Uani 1 1 d . . . . .
C1 C 0.1178(2) 0.76290(16) 0.81302(12) 0.0341(4) Uani 1 1 d . . . . .
C2 C 0.0350(3) 0.86530(17) 0.87437(14) 0.0434(5) Uani 1 1 d . . . . .
H2 H -0.045528 0.826365 0.921905 0.052 Uiso 1 1 calc R . . . .
C3 C 0.1996(3) 0.9486(2) 0.93308(18) 0.0599(6) Uani 1 1 d . . . . .
H3A H 0.218627 0.924414 1.003259 0.072 Uiso 1 1 calc R . . . .
H3B H 0.179162 1.035929 0.934032 0.072 Uiso 1 1 calc R . . . .
C4 C 0.3671(3) 0.9305(2) 0.87755(17) 0.0562(6) Uani 1 1 d . . . . .
H4A H 0.457602 0.894671 0.922090 0.067 Uiso 1 1 calc R . . . .
H4B H 0.423327 1.010190 0.856214 0.067 Uiso 1 1 calc R . . . .
C5 C 0.2941(3) 0.84030(18) 0.78396(15) 0.0446(5) Uani 1 1 d . . . . .
H5A H 0.383807 0.785629 0.769465 0.053 Uiso 1 1 calc R . . . .
H5B H 0.266329 0.886853 0.723973 0.053 Uiso 1 1 calc R . . . .
C6 C -0.0750(4) 0.9303(2) 0.79221(18) 0.0642(7) Uani 1 1 d . . . . .
H6A H -0.193771 0.942004 0.813053 0.077 Uiso 1 1 calc R . . . .
H6B H -0.009726 1.011890 0.781013 0.077 Uiso 1 1 calc R . . . .
C7 C -0.0979(3) 0.8458(2) 0.69613(16) 0.0535(5) Uani 1 1 d . . . . .
C8 C -0.0265(2) 0.72228(16) 0.71894(13) 0.0360(4) Uani 1 1 d . . . . .
C9 C -0.1908(3) 0.6299(2) 0.74461(15) 0.0495(5) Uani 1 1 d . . . . .
H9A H -0.147905 0.551996 0.764437 0.059 Uiso 1 1 calc R . . . .
H9B H -0.241583 0.665412 0.802610 0.059 Uiso 1 1 calc R . . . .
C10 C -0.3416(3) 0.6015(3) 0.65468(18) 0.0670(7) Uani 1 1 d . . . . .
H10A H -0.395947 0.677262 0.640489 0.080 Uiso 1 1 calc R . . . .
H10B H -0.437073 0.538722 0.673064 0.080 Uiso 1 1 calc R . . . .
C11 C -0.2678(3) 0.5537(3) 0.55841(19) 0.0697(7) Uani 1 1 d . . . . .
H11A H -0.250931 0.466421 0.565513 0.084 Uiso 1 1 calc R . . . .
H11B H -0.359755 0.556515 0.500328 0.084 Uiso 1 1 calc R . . . .
C12 C -0.0921(3) 0.62400(19) 0.53508(14) 0.0453(5) Uani 1 1 d . . . . .
C13 C 0.0494(3) 0.66870(18) 0.62466(13) 0.0390(4) Uani 1 1 d . . . . .
H13A H 0.138718 0.732962 0.602437 0.047 Uiso 1 1 calc R . . . .
H13B H 0.113430 0.598870 0.644855 0.047 Uiso 1 1 calc R . . . .
C14 C 0.1636(3) 0.65946(17) 0.88474(13) 0.0394(4) Uani 1 1 d . . . . .
H14A H 0.243266 0.698689 0.944153 0.047 Uiso 1 1 calc R . . . .
H14B H 0.050637 0.622051 0.908721 0.047 Uiso 1 1 calc R . . . .
C15 C 0.2541(4) 0.5560(2) 0.84004(15) 0.0563(6) Uani 1 1 d . . . . .
H15A H 0.167629 0.503124 0.790265 0.068 Uiso 1 1 calc R . . . .
H15B H 0.357462 0.590857 0.806003 0.068 Uiso 1 1 calc R . . . .
C16 C 0.3772(3) 0.28593(17) 0.81379(14) 0.0383(4) Uani 1 1 d . . . . .
C17 C 0.2771(3) 0.2330(2) 0.72391(15) 0.0481(5) Uani 1 1 d . . . . .
H17 H 0.149730 0.226612 0.715948 0.058 Uiso 1 1 calc R . . . .
C18 C 0.3679(3) 0.1898(2) 0.64604(16) 0.0536(5) Uani 1 1 d . . . . .
H18 H 0.300414 0.154108 0.585564 0.064 Uiso 1 1 calc R . . . .
C19 C 0.5572(3) 0.19833(19) 0.65598(16) 0.0483(5) Uani 1 1 d . . . . .
C20 C 0.6551(3) 0.2536(2) 0.74670(17) 0.0559(5) Uani 1 1 d . . . . .
H20 H 0.782584 0.261154 0.754380 0.067 Uiso 1 1 calc R . . . .
C21 C 0.5670(3) 0.2975(2) 0.82537(16) 0.0511(5) Uani 1 1 d . . . . .
H21 H 0.634249 0.334452 0.885505 0.061 Uiso 1 1 calc R . . . .
C22 C 0.6562(4) 0.1505(3) 0.5712(2) 0.0717(7) Uani 1 1 d . . . . .
H22A H 0.673059 0.064624 0.580882 0.107 Uiso 1 1 calc GR . . . .
H22B H 0.773649 0.200730 0.572276 0.107 Uiso 1 1 calc GR . . . .
H22C H 0.584926 0.155781 0.506345 0.107 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 O3 1.5643(15) . ?
S1 O4 1.4187(17) . ?
S1 O5 1.4233(14) . ?
S1 C16 1.7526(19) . ?
O1 C7 1.204(3) . ?
O2 C12 1.213(2) . ?
O3 C15 1.467(2) . ?
C1 C2 1.562(2) . ?
C1 C5 1.547(3) . ?
C1 C8 1.550(2) . ?
C1 C14 1.537(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.526(3) . ?
C2 C6 1.530(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.534(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.535(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.503(3) . ?
C7 C8 1.521(3) . ?
C8 C9 1.544(3) . ?
C8 C13 1.534(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.526(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.485(3) . ?
C12 C13 1.504(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.500(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.381(3) . ?
C16 C21 1.385(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(3) . ?
C19 C20 1.392(3) . ?
C19 C22 1.505(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O3 S1 C16 104.68(9) . . ?
O4 S1 O3 110.01(10) . . ?
O4 S1 O5 118.99(10) . . ?
O4 S1 C16 108.56(10) . . ?
O5 S1 O3 103.76(8) . . ?
O5 S1 C16 109.87(9) . . ?
C15 O3 S1 118.53(13) . . ?
C5 C1 C2 101.02(15) . . ?
C5 C1 C8 112.67(14) . . ?
C8 C1 C2 104.78(14) . . ?
C14 C1 C2 108.99(14) . . ?
C14 C1 C5 111.36(15) . . ?
C14 C1 C8 116.55(15) . . ?
C1 C2 H2 110.6 . . ?
C3 C2 C1 105.41(16) . . ?
C3 C2 H2 110.6 . . ?
C3 C2 C6 114.92(19) . . ?
C6 C2 C1 104.44(15) . . ?
C6 C2 H2 110.6 . . ?
C2 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C2 C3 C4 107.06(16) . . ?
H3A C3 H3B 108.6 . . ?
C4 C3 H3A 110.3 . . ?
C4 C3 H3B 110.3 . . ?
C3 C4 H4A 110.6 . . ?
C3 C4 H4B 110.6 . . ?
C3 C4 C5 105.77(17) . . ?
H4A C4 H4B 108.7 . . ?
C5 C4 H4A 110.6 . . ?
C5 C4 H4B 110.6 . . ?
C1 C5 H5A 110.6 . . ?
C1 C5 H5B 110.6 . . ?
C4 C5 C1 105.55(16) . . ?
C4 C5 H5A 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.8 . . ?
C2 C6 H6A 110.4 . . ?
C2 C6 H6B 110.4 . . ?
H6A C6 H6B 108.6 . . ?
C7 C6 C2 106.43(16) . . ?
C7 C6 H6A 110.4 . . ?
C7 C6 H6B 110.4 . . ?
O1 C7 C6 125.9(2) . . ?
O1 C7 C8 123.96(19) . . ?
C6 C7 C8 110.11(16) . . ?
C7 C8 C1 101.52(14) . . ?
C7 C8 C9 107.08(17) . . ?
C7 C8 C13 110.37(15) . . ?
C9 C8 C1 113.00(15) . . ?
C13 C8 C1 115.16(15) . . ?
C13 C8 C9 109.19(15) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 C8 112.59(18) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C9 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C9 C10 C11 111.75(18) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 C10 115.52(19) . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
O2 C12 C11 121.44(19) . . ?
O2 C12 C13 121.2(2) . . ?
C11 C12 C13 116.98(17) . . ?
C8 C13 H13A 108.5 . . ?
C8 C13 H13B 108.5 . . ?
C12 C13 C8 115.08(16) . . ?
C12 C13 H13A 108.5 . . ?
C12 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C1 C14 H14A 108.2 . . ?
C1 C14 H14B 108.2 . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 C1 116.42(15) . . ?
C15 C14 H14A 108.2 . . ?
C15 C14 H14B 108.2 . . ?
O3 C15 C14 107.22(15) . . ?
O3 C15 H15A 110.3 . . ?
O3 C15 H15B 110.3 . . ?
C14 C15 H15A 110.3 . . ?
C14 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
C17 C16 S1 119.88(15) . . ?
C17 C16 C21 120.52(18) . . ?
C21 C16 S1 119.59(15) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.37(19) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.41(19) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 118.2(2) . . ?
C18 C19 C22 121.4(2) . . ?
C20 C19 C22 120.5(2) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(2) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.4 . . ?
C20 C21 C16 119.19(19) . . ?
C20 C21 H21 120.4 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 O3 C15 C14 129.19(17) . . . . ?
S1 C16 C17 C18 -177.76(15) . . . . ?
S1 C16 C21 C20 177.72(16) . . . . ?
O1 C7 C8 C1 153.2(3) . . . . ?
O1 C7 C8 C9 -88.1(3) . . . . ?
O1 C7 C8 C13 30.6(3) . . . . ?
O2 C12 C13 C8 145.46(18) . . . . ?
O3 S1 C16 C17 -114.09(16) . . . . ?
O3 S1 C16 C21 67.10(17) . . . . ?
O4 S1 O3 C15 -51.34(17) . . . . ?
O4 S1 C16 C17 3.36(19) . . . . ?
O4 S1 C16 C21 -175.45(16) . . . . ?
O5 S1 O3 C15 -179.67(15) . . . . ?
O5 S1 C16 C17 135.05(16) . . . . ?
O5 S1 C16 C21 -43.77(18) . . . . ?
C1 C2 C3 C4 21.5(2) . . . . ?
C1 C2 C6 C7 15.5(3) . . . . ?
C1 C8 C9 C10 173.83(17) . . . . ?
C1 C8 C13 C12 177.39(15) . . . . ?
C1 C14 C15 O3 169.42(17) . . . . ?
C2 C1 C5 C4 37.89(18) . . . . ?
C2 C1 C8 C7 35.27(18) . . . . ?
C2 C1 C8 C9 -79.06(18) . . . . ?
C2 C1 C8 C13 154.50(15) . . . . ?
C2 C1 C14 C15 -176.90(18) . . . . ?
C2 C3 C4 C5 2.4(2) . . . . ?
C2 C6 C7 O1 -172.6(3) . . . . ?
C2 C6 C7 C8 7.1(3) . . . . ?
C3 C2 C6 C7 130.4(2) . . . . ?
C3 C4 C5 C1 -25.6(2) . . . . ?
C5 C1 C2 C3 -36.25(19) . . . . ?
C5 C1 C2 C6 85.23(19) . . . . ?
C5 C1 C8 C7 -73.66(18) . . . . ?
C5 C1 C8 C9 172.00(16) . . . . ?
C5 C1 C8 C13 45.6(2) . . . . ?
C5 C1 C14 C15 -66.3(2) . . . . ?
C6 C2 C3 C4 -92.9(2) . . . . ?
C6 C7 C8 C1 -26.5(2) . . . . ?
C6 C7 C8 C9 92.2(2) . . . . ?
C6 C7 C8 C13 -149.1(2) . . . . ?
C7 C8 C9 C10 62.9(2) . . . . ?
C7 C8 C13 C12 -68.4(2) . . . . ?
C8 C1 C2 C3 -153.48(16) . . . . ?
C8 C1 C2 C6 -32.0(2) . . . . ?
C8 C1 C5 C4 149.17(16) . . . . ?
C8 C1 C14 C15 64.8(2) . . . . ?
C8 C9 C10 C11 54.8(3) . . . . ?
C9 C8 C13 C12 49.0(2) . . . . ?
C9 C10 C11 C12 -44.6(3) . . . . ?
C10 C11 C12 O2 -148.4(2) . . . . ?
C10 C11 C12 C13 38.3(3) . . . . ?
C11 C12 C13 C8 -41.2(3) . . . . ?
C13 C8 C9 C10 -56.6(2) . . . . ?
C14 C1 C2 C3 81.1(2) . . . . ?
C14 C1 C2 C6 -157.42(18) . . . . ?
C14 C1 C5 C4 -77.72(19) . . . . ?
C14 C1 C8 C7 155.80(16) . . . . ?
C14 C1 C8 C9 41.5(2) . . . . ?
C14 C1 C8 C13 -85.0(2) . . . . ?
C16 S1 O3 C15 65.12(16) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C16 C21 C20 -1.1(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C17 C18 C19 C22 179.7(2) . . . . ?
C18 C19 C20 C21 0.8(3) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
C21 C16 C17 C18 1.0(3) . . . . ?
C22 C19 C20 C21 -179.7(2) . . . . ?

_olex2_date_sample_data_collection 2019-06-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.618
_oxdiff_exptl_absorpt_empirical_full_min 0.443
####################################################################### 
# 
# 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_zhangye_1015
_database_code_depnum_ccdc_archive 'CCDC 1962275'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-10-18
_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         '2(C15 H22 O3)'
_chemical_formula_sum            'C30 H44 O6'
_chemical_formula_weight         500.65
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.6688(3)
_cell_length_b                   22.4305(6)
_cell_length_c                   15.4747(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.329(4)
_cell_angle_gamma                90
_cell_volume                     2610.00(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5177
_cell_measurement_temperature    292.89(12)
_cell_measurement_theta_max      69.4980
_cell_measurement_theta_min      6.1850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12604
_diffrn_reflns_point_group_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         3.517
_diffrn_ambient_temperature      292.89(12)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00  -15.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  5 omega   23.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega  -14.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 62

#__ type_ start__ end____ width___ exp.time_
 11 omega   76.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega  102.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000    0.0000 74

#__ type_ start__ end____ width___ exp.time_
 13 omega   76.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 15 omega   69.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 28

#__ type_ start__ end____ width___ exp.time_
 16 omega   35.00   61.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   59.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
 19 omega  -49.00  -23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  111.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega  -16.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
 22 omega   51.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega  150.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 24 omega   53.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   45.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega  110.00  136.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   90.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 28 omega   59.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1221208000
_diffrn_orient_matrix_UB_12      -0.0452613000
_diffrn_orient_matrix_UB_13      0.0337416000
_diffrn_orient_matrix_UB_21      0.1404157000
_diffrn_orient_matrix_UB_22      -0.0082940000
_diffrn_orient_matrix_UB_23      0.0851597000
_diffrn_orient_matrix_UB_31      -0.0855389000
_diffrn_orient_matrix_UB_32      0.0509989000
_diffrn_orient_matrix_UB_33      0.0438501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3722
_reflns_number_total             4422
_reflns_odcompleteness_completeness 95.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.279
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4422
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.063
_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)+(0.0703P)²+0.4835P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1371
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C15(H15A,H15B), C19(H19A,H19B), C21(H21A,H21B),
 C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C30(H30A,H30B), C32(H32A,H32B),
  C11(H11A,H11B), C14(H14A,H14B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,
 H28B), C31(H31A,H31B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B),
 C36(H36A,H36B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6)
;
_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 0.04753(17) 0.03278(6) 0.60409(8) 0.0459(3) Uani 1 1 d . . . . .
O2 O 0.5369(2) -0.05159(7) 0.87537(9) 0.0593(4) Uani 1 1 d . . . . .
O3 O 0.1006(2) -0.06466(6) 0.56750(8) 0.0583(4) Uani 1 1 d . . . . .
H3 H 0.056875 -0.054452 0.517014 0.087 Uiso 1 1 calc GR . . . .
C7 C 0.3962(2) -0.02565(7) 0.85918(11) 0.0415(4) Uani 1 1 d . . . . .
C8 C 0.4781(2) 0.03800(8) 0.73745(12) 0.0456(4) Uani 1 1 d . . . . .
H8A H 0.527818 0.071247 0.774264 0.055 Uiso 1 1 calc R . . . .
H8B H 0.571101 0.008429 0.739567 0.055 Uiso 1 1 calc R . . . .
C9 C 0.4207(3) 0.05988(8) 0.64256(13) 0.0493(4) Uani 1 1 d . . . . .
H9A H 0.338114 0.092808 0.640972 0.059 Uiso 1 1 calc R . . . .
H9B H 0.523896 0.074322 0.621361 0.059 Uiso 1 1 calc R . . . .
C10 C 0.3258(2) 0.01060(7) 0.77558(10) 0.0352(3) Uani 1 1 d . . . . .
C13 C 0.1985(2) 0.05438(7) 0.81048(11) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.2292(2) -0.03655(7) 0.71066(10) 0.0373(4) Uani 1 1 d . . . . .
H15A H 0.306477 -0.070890 0.711616 0.045 Uiso 1 1 calc R . . . .
H15B H 0.123524 -0.049578 0.730936 0.045 Uiso 1 1 calc R . . . .
C18 C 0.1750(3) -0.01474(7) 0.61598(11) 0.0412(4) Uani 1 1 d . . . . .
C19 C 0.0526(3) 0.08439(8) 0.74263(12) 0.0466(4) Uani 1 1 d . . . . .
H19A H -0.030664 0.102970 0.774086 0.056 Uiso 1 1 calc R . . . .
H19B H 0.107142 0.116015 0.714376 0.056 Uiso 1 1 calc R . . . .
C21 C 0.2622(3) -0.02571(8) 0.91829(12) 0.0503(5) Uani 1 1 d . . . . .
H21A H 0.317604 -0.013353 0.977391 0.060 Uiso 1 1 calc R . . . .
H21B H 0.213043 -0.065325 0.921286 0.060 Uiso 1 1 calc R . . . .
C22 C 0.1166(2) 0.01804(7) 0.87839(11) 0.0413(4) Uani 1 1 d . . . . .
H22 H 0.009532 -0.003212 0.849092 0.050 Uiso 1 1 calc R . . . .
C23 C -0.0518(2) 0.04528(10) 0.67133(13) 0.0522(5) Uani 1 1 d . . . . .
H23A H -0.081435 0.008130 0.697130 0.063 Uiso 1 1 calc R . . . .
H23B H -0.162053 0.065076 0.645251 0.063 Uiso 1 1 calc R . . . .
C24 C 0.3324(3) 0.01016(8) 0.58240(12) 0.0484(4) Uani 1 1 d . . . . .
H24A H 0.292982 0.025557 0.523209 0.058 Uiso 1 1 calc R . . . .
H24B H 0.417799 -0.021386 0.579993 0.058 Uiso 1 1 calc R . . . .
C26 C 0.3040(3) 0.10223(7) 0.87111(13) 0.0493(4) Uani 1 1 d . . . . .
H26A H 0.416412 0.086208 0.902203 0.059 Uiso 1 1 calc R . . . .
H26B H 0.327542 0.136549 0.837025 0.059 Uiso 1 1 calc R . . . .
C30 C 0.1860(4) 0.11960(9) 0.93593(15) 0.0622(6) Uani 1 1 d . . . . .
H30A H 0.112043 0.153546 0.914018 0.075 Uiso 1 1 calc R . . . .
H30B H 0.257901 0.129797 0.992829 0.075 Uiso 1 1 calc R . . . .
C32 C 0.0708(3) 0.06459(9) 0.94365(14) 0.0571(5) Uani 1 1 d . . . . .
H32A H -0.054439 0.074855 0.928865 0.069 Uiso 1 1 calc R . . . .
H32B H 0.096833 0.049025 1.003284 0.069 Uiso 1 1 calc R . . . .
O4 O 0.41418(19) 0.14656(6) 0.31948(11) 0.0588(4) Uani 1 1 d . . . . .
O5 O -0.21544(19) 0.25459(7) 0.30998(11) 0.0661(4) Uani 1 1 d . . . . .
O6 O 0.2053(2) 0.09146(6) 0.22396(11) 0.0629(4) Uani 1 1 d . . . . .
H6 H 0.282930 0.080697 0.197732 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.0910(2) 0.16507(7) 0.30249(11) 0.0401(4) Uani 1 1 d . . . . .
H11A H 0.084068 0.136396 0.348611 0.048 Uiso 1 1 calc R . . . .
H11B H -0.017252 0.161533 0.258264 0.048 Uiso 1 1 calc R . . . .
C12 C -0.0889(2) 0.23622(7) 0.36173(13) 0.0444(4) Uani 1 1 d . . . . .
C14 C 0.2232(3) 0.29700(7) 0.47324(13) 0.0483(4) Uani 1 1 d . . . . .
H14A H 0.332631 0.316049 0.465416 0.058 Uiso 1 1 calc R . . . .
H14B H 0.123611 0.320310 0.442469 0.058 Uiso 1 1 calc R . . . .
C16 C 0.2134(2) 0.23228(7) 0.43667(12) 0.0383(4) Uani 1 1 d . . . . .
C17 C 0.0991(2) 0.22862(7) 0.34258(11) 0.0385(4) Uani 1 1 d . . . . .
C20 C 0.0999(3) 0.20157(7) 0.49691(12) 0.0443(4) Uani 1 1 d . . . . .
H20 H 0.119719 0.158390 0.498787 0.053 Uiso 1 1 calc R . . . .
C25 C 0.4014(2) 0.20602(8) 0.44980(14) 0.0508(5) Uani 1 1 d . . . . .
H25A H 0.474754 0.233360 0.423956 0.061 Uiso 1 1 calc R . . . .
H25B H 0.449596 0.204560 0.512592 0.061 Uiso 1 1 calc R . . . .
C27 C 0.4202(3) 0.14442(8) 0.41194(15) 0.0554(5) Uani 1 1 d . . . . .
H27A H 0.532319 0.127034 0.440964 0.067 Uiso 1 1 calc R . . . .
H27B H 0.325124 0.119034 0.423630 0.067 Uiso 1 1 calc R . . . .
C28 C 0.1358(3) 0.27356(8) 0.27377(13) 0.0519(5) Uani 1 1 d . . . . .
H28A H 0.029438 0.277540 0.228425 0.062 Uiso 1 1 calc R . . . .
H28B H 0.160021 0.312135 0.301908 0.062 Uiso 1 1 calc R . . . .
C29 C 0.2477(3) 0.14891(8) 0.26057(14) 0.0488(4) Uani 1 1 d . . . . .
C31 C -0.0916(3) 0.21605(9) 0.45408(14) 0.0535(5) Uani 1 1 d . . . . .
H31A H -0.166140 0.181022 0.453203 0.064 Uiso 1 1 calc R . . . .
H31B H -0.137884 0.247356 0.486512 0.064 Uiso 1 1 calc R . . . .
C33 C 0.2711(4) 0.19407(10) 0.19081(16) 0.0667(6) Uani 1 1 d . . . . .
H33A H 0.168779 0.192759 0.142720 0.080 Uiso 1 1 calc R . . . .
H33B H 0.375843 0.184122 0.167394 0.080 Uiso 1 1 calc R . . . .
C34 C 0.2910(3) 0.25694(9) 0.23003(16) 0.0654(6) Uani 1 1 d . . . . .
H34A H 0.400998 0.259281 0.273295 0.079 Uiso 1 1 calc R . . . .
H34B H 0.298058 0.285412 0.183668 0.079 Uiso 1 1 calc R . . . .
C35 C 0.2173(4) 0.29262(10) 0.57095(16) 0.0733(7) Uani 1 1 d . . . . .
H35A H 0.132274 0.320954 0.585861 0.088 Uiso 1 1 calc R . . . .
H35B H 0.333350 0.301357 0.606486 0.088 Uiso 1 1 calc R . . . .
C36 C 0.1617(3) 0.22913(9) 0.58824(14) 0.0620(6) Uani 1 1 d . . . . .
H36A H 0.065838 0.229315 0.620851 0.074 Uiso 1 1 calc R . . . .
H36B H 0.261210 0.206997 0.621625 0.074 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 C18 1.433(2) . ?
O1 C23 1.433(2) . ?
O2 C7 1.208(2) . ?
O3 H3 0.8200 . ?
O3 C18 1.405(2) . ?
C7 C10 1.534(2) . ?
C7 C21 1.504(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.529(3) . ?
C8 C10 1.536(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C24 1.524(3) . ?
C10 C13 1.555(2) . ?
C10 C15 1.544(2) . ?
C13 C19 1.531(2) . ?
C13 C22 1.556(2) . ?
C13 C26 1.546(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C18 1.523(2) . ?
C18 C24 1.511(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C23 1.510(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.524(2) . ?
C22 H22 0.9800 . ?
C22 C32 1.540(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C30 1.527(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 C32 1.536(3) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
O4 C27 1.423(3) . ?
O4 C29 1.417(3) . ?
O5 C12 1.203(2) . ?
O6 H6 0.8200 . ?
O6 C29 1.419(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C17 1.551(2) . ?
C11 C29 1.517(2) . ?
C12 C17 1.537(2) . ?
C12 C31 1.503(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C16 1.555(2) . ?
C14 C35 1.525(3) . ?
C16 C17 1.547(2) . ?
C16 C20 1.555(2) . ?
C16 C25 1.534(2) . ?
C17 C28 1.532(2) . ?
C20 H20 0.9800 . ?
C20 C31 1.523(3) . ?
C20 C36 1.530(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C27 1.519(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 C34 1.526(3) . ?
C29 C33 1.517(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.531(3) . ?
C34 H34A 0.9700 . ?
C34 H34B 0.9700 . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C35 C36 1.525(3) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?

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
C23 O1 C18 119.92(13) . . ?
C18 O3 H3 109.5 . . ?
O2 C7 C10 125.62(17) . . ?
O2 C7 C21 124.23(16) . . ?
C21 C7 C10 110.14(15) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C9 C8 C10 113.61(15) . . ?
C10 C8 H8A 108.8 . . ?
C10 C8 H8B 108.8 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C24 C9 C8 111.18(14) . . ?
C24 C9 H9A 109.4 . . ?
C24 C9 H9B 109.4 . . ?
C7 C10 C8 111.60(14) . . ?
C7 C10 C13 100.54(13) . . ?
C7 C10 C15 103.30(12) . . ?
C8 C10 C13 117.22(13) . . ?
C8 C10 C15 109.13(14) . . ?
C15 C10 C13 113.88(14) . . ?
C10 C13 C22 105.56(12) . . ?
C19 C13 C10 117.62(14) . . ?
C19 C13 C22 110.84(14) . . ?
C19 C13 C26 109.62(14) . . ?
C26 C13 C10 111.09(14) . . ?
C26 C13 C22 100.74(13) . . ?
C10 C15 H15A 108.7 . . ?
C10 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C18 C15 C10 114.28(13) . . ?
C18 C15 H15A 108.7 . . ?
C18 C15 H15B 108.7 . . ?
O1 C18 C15 114.38(14) . . ?
O1 C18 C24 104.57(13) . . ?
O3 C18 O1 109.22(15) . . ?
O3 C18 C15 105.25(13) . . ?
O3 C18 C24 112.25(15) . . ?
C24 C18 C15 111.34(15) . . ?
C13 C19 H19A 108.0 . . ?
C13 C19 H19B 108.0 . . ?
H19A C19 H19B 107.2 . . ?
C23 C19 C13 117.17(15) . . ?
C23 C19 H19A 108.0 . . ?
C23 C19 H19B 108.0 . . ?
C7 C21 H21A 110.4 . . ?
C7 C21 H21B 110.4 . . ?
C7 C21 C22 106.68(14) . . ?
H21A C21 H21B 108.6 . . ?
C22 C21 H21A 110.4 . . ?
C22 C21 H21B 110.4 . . ?
C13 C22 H22 110.8 . . ?
C21 C22 C13 104.47(14) . . ?
C21 C22 H22 110.8 . . ?
C21 C22 C32 114.48(16) . . ?
C32 C22 C13 105.19(14) . . ?
C32 C22 H22 110.8 . . ?
O1 C23 C19 111.27(16) . . ?
O1 C23 H23A 109.4 . . ?
O1 C23 H23B 109.4 . . ?
C19 C23 H23A 109.4 . . ?
C19 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C9 C24 H24A 109.6 . . ?
C9 C24 H24B 109.6 . . ?
C18 C24 C9 110.46(15) . . ?
C18 C24 H24A 109.6 . . ?
C18 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C13 C26 H26A 110.6 . . ?
C13 C26 H26B 110.6 . . ?
H26A C26 H26B 108.8 . . ?
C30 C26 C13 105.59(16) . . ?
C30 C26 H26A 110.6 . . ?
C30 C26 H26B 110.6 . . ?
C26 C30 H30A 110.6 . . ?
C26 C30 H30B 110.6 . . ?
C26 C30 C32 105.68(15) . . ?
H30A C30 H30B 108.7 . . ?
C32 C30 H30A 110.6 . . ?
C32 C30 H30B 110.6 . . ?
C22 C32 H32A 110.4 . . ?
C22 C32 H32B 110.4 . . ?
C30 C32 C22 106.54(16) . . ?
C30 C32 H32A 110.4 . . ?
C30 C32 H32B 110.4 . . ?
H32A C32 H32B 108.6 . . ?
C29 O4 C27 119.70(15) . . ?
C29 O6 H6 109.5 . . ?
H11A C11 H11B 107.6 . . ?
C17 C11 H11A 108.6 . . ?
C17 C11 H11B 108.6 . . ?
C29 C11 H11A 108.6 . . ?
C29 C11 H11B 108.6 . . ?
C29 C11 C17 114.71(14) . . ?
O5 C12 C17 125.05(18) . . ?
O5 C12 C31 125.15(18) . . ?
C31 C12 C17 109.80(15) . . ?
H14A C14 H14B 108.6 . . ?
C16 C14 H14A 110.3 . . ?
C16 C14 H14B 110.3 . . ?
C35 C14 H14A 110.3 . . ?
C35 C14 H14B 110.3 . . ?
C35 C14 C16 106.98(15) . . ?
C14 C16 C20 100.85(14) . . ?
C17 C16 C14 111.72(13) . . ?
C17 C16 C20 105.10(14) . . ?
C25 C16 C14 109.46(14) . . ?
C25 C16 C17 116.64(15) . . ?
C25 C16 C20 111.88(15) . . ?
C12 C17 C11 102.35(13) . . ?
C12 C17 C16 101.08(14) . . ?
C16 C17 C11 113.32(13) . . ?
C28 C17 C11 108.96(14) . . ?
C28 C17 C12 111.62(15) . . ?
C28 C17 C16 118.14(14) . . ?
C16 C20 H20 110.7 . . ?
C31 C20 C16 104.48(14) . . ?
C31 C20 H20 110.7 . . ?
C31 C20 C36 114.39(17) . . ?
C36 C20 C16 105.47(15) . . ?
C36 C20 H20 110.7 . . ?
C16 C25 H25A 108.0 . . ?
C16 C25 H25B 108.0 . . ?
H25A C25 H25B 107.2 . . ?
C27 C25 C16 117.17(15) . . ?
C27 C25 H25A 108.0 . . ?
C27 C25 H25B 108.0 . . ?
O4 C27 C25 111.74(17) . . ?
O4 C27 H27A 109.3 . . ?
O4 C27 H27B 109.3 . . ?
C25 C27 H27A 109.3 . . ?
C25 C27 H27B 109.3 . . ?
H27A C27 H27B 107.9 . . ?
C17 C28 H28A 108.7 . . ?
C17 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C34 C28 C17 114.42(16) . . ?
C34 C28 H28A 108.7 . . ?
C34 C28 H28B 108.7 . . ?
O4 C29 O6 109.25(16) . . ?
O4 C29 C11 115.04(16) . . ?
O4 C29 C33 105.37(17) . . ?
O6 C29 C11 104.43(15) . . ?
O6 C29 C33 111.85(17) . . ?
C33 C29 C11 111.05(17) . . ?
C12 C31 C20 106.58(15) . . ?
C12 C31 H31A 110.4 . . ?
C12 C31 H31B 110.4 . . ?
C20 C31 H31A 110.4 . . ?
C20 C31 H31B 110.4 . . ?
H31A C31 H31B 108.6 . . ?
C29 C33 H33A 109.6 . . ?
C29 C33 H33B 109.6 . . ?
C29 C33 C34 110.46(18) . . ?
H33A C33 H33B 108.1 . . ?
C34 C33 H33A 109.6 . . ?
C34 C33 H33B 109.6 . . ?
C28 C34 C33 112.04(18) . . ?
C28 C34 H34A 109.2 . . ?
C28 C34 H34B 109.2 . . ?
C33 C34 H34A 109.2 . . ?
C33 C34 H34B 109.2 . . ?
H34A C34 H34B 107.9 . . ?
C14 C35 H35A 110.2 . . ?
C14 C35 H35B 110.2 . . ?
C14 C35 C36 107.33(16) . . ?
H35A C35 H35B 108.5 . . ?
C36 C35 H35A 110.2 . . ?
C36 C35 H35B 110.2 . . ?
C20 C36 H36A 110.7 . . ?
C20 C36 H36B 110.7 . . ?
C35 C36 C20 105.17(17) . . ?
C35 C36 H36A 110.7 . . ?
C35 C36 H36B 110.7 . . ?
H36A C36 H36B 108.8 . . ?

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 C18 C24 C9 67.72(17) . . . . ?
O2 C7 C10 C8 -29.6(2) . . . . ?
O2 C7 C10 C13 -154.62(18) . . . . ?
O2 C7 C10 C15 87.5(2) . . . . ?
O2 C7 C21 C22 173.39(17) . . . . ?
O3 C18 C24 C9 -174.00(14) . . . . ?
C7 C10 C13 C19 -159.37(15) . . . . ?
C7 C10 C13 C22 -35.15(16) . . . . ?
C7 C10 C13 C26 73.19(16) . . . . ?
C7 C10 C15 C18 -169.29(15) . . . . ?
C7 C21 C22 C13 -14.63(18) . . . . ?
C7 C21 C22 C32 -129.14(17) . . . . ?
C8 C9 C24 C18 56.9(2) . . . . ?
C8 C10 C13 C19 79.51(19) . . . . ?
C8 C10 C13 C22 -156.26(14) . . . . ?
C8 C10 C13 C26 -47.9(2) . . . . ?
C8 C10 C15 C18 -50.45(19) . . . . ?
C9 C8 C10 C7 164.34(14) . . . . ?
C9 C8 C10 C13 -80.52(19) . . . . ?
C9 C8 C10 C15 50.81(19) . . . . ?
C10 C7 C21 C22 -7.9(2) . . . . ?
C10 C8 C9 C24 -55.6(2) . . . . ?
C10 C13 C19 C23 45.4(2) . . . . ?
C10 C13 C22 C21 31.69(17) . . . . ?
C10 C13 C22 C32 152.59(15) . . . . ?
C10 C13 C26 C30 -151.01(15) . . . . ?
C10 C15 C18 O1 -63.7(2) . . . . ?
C10 C15 C18 O3 176.41(15) . . . . ?
C10 C15 C18 C24 54.55(19) . . . . ?
C13 C10 C15 C18 82.64(18) . . . . ?
C13 C19 C23 O1 -77.8(2) . . . . ?
C13 C22 C32 C30 -21.2(2) . . . . ?
C13 C26 C30 C32 27.3(2) . . . . ?
C15 C10 C13 C19 -49.60(19) . . . . ?
C15 C10 C13 C22 74.62(16) . . . . ?
C15 C10 C13 C26 -177.04(13) . . . . ?
C15 C18 C24 C9 -56.29(19) . . . . ?
C18 O1 C23 C19 83.4(2) . . . . ?
C19 C13 C22 C21 160.07(14) . . . . ?
C19 C13 C22 C32 -79.03(18) . . . . ?
C19 C13 C26 C30 77.31(19) . . . . ?
C21 C7 C10 C8 151.74(15) . . . . ?
C21 C7 C10 C13 26.70(17) . . . . ?
C21 C7 C10 C15 -91.14(16) . . . . ?
C21 C22 C32 C30 92.9(2) . . . . ?
C22 C13 C19 C23 -76.10(19) . . . . ?
C22 C13 C26 C30 -39.56(18) . . . . ?
C23 O1 C18 O3 101.39(17) . . . . ?
C23 O1 C18 C15 -16.2(2) . . . . ?
C23 O1 C18 C24 -138.29(16) . . . . ?
C26 C13 C19 C23 173.58(16) . . . . ?
C26 C13 C22 C21 -83.96(16) . . . . ?
C26 C13 C22 C32 36.93(18) . . . . ?
C26 C30 C32 C22 -3.6(2) . . . . ?
O4 C29 C33 C34 -69.2(2) . . . . ?
O5 C12 C17 C11 -87.3(2) . . . . ?
O5 C12 C17 C16 155.60(17) . . . . ?
O5 C12 C17 C28 29.1(2) . . . . ?
O5 C12 C31 C20 -175.47(17) . . . . ?
O6 C29 C33 C34 172.18(19) . . . . ?
C11 C17 C28 C34 -49.2(2) . . . . ?
C11 C29 C33 C34 55.9(3) . . . . ?
C12 C17 C28 C34 -161.48(17) . . . . ?
C14 C16 C17 C11 178.09(15) . . . . ?
C14 C16 C17 C12 -73.14(17) . . . . ?
C14 C16 C17 C28 48.9(2) . . . . ?
C14 C16 C20 C31 83.12(16) . . . . ?
C14 C16 C20 C36 -37.81(18) . . . . ?
C14 C16 C25 C27 -175.61(17) . . . . ?
C14 C35 C36 C20 -11.2(3) . . . . ?
C16 C14 C35 C36 -12.8(3) . . . . ?
C16 C17 C28 C34 82.0(2) . . . . ?
C16 C20 C31 C12 16.76(18) . . . . ?
C16 C20 C36 C35 31.1(2) . . . . ?
C16 C25 C27 O4 78.9(2) . . . . ?
C17 C11 C29 O4 64.1(2) . . . . ?
C17 C11 C29 O6 -176.21(15) . . . . ?
C17 C11 C29 C33 -55.5(2) . . . . ?
C17 C12 C31 C20 5.73(19) . . . . ?
C17 C16 C20 C31 -33.11(16) . . . . ?
C17 C16 C20 C36 -154.04(15) . . . . ?
C17 C16 C25 C27 -47.6(2) . . . . ?
C17 C28 C34 C33 53.4(3) . . . . ?
C20 C16 C17 C11 -73.40(17) . . . . ?
C20 C16 C17 C12 35.37(15) . . . . ?
C20 C16 C17 C28 157.41(15) . . . . ?
C20 C16 C25 C27 73.5(2) . . . . ?
C25 C16 C17 C11 51.1(2) . . . . ?
C25 C16 C17 C12 159.92(14) . . . . ?
C25 C16 C17 C28 -78.04(19) . . . . ?
C25 C16 C20 C31 -160.62(15) . . . . ?
C25 C16 C20 C36 78.46(18) . . . . ?
C27 O4 C29 O6 -101.76(18) . . . . ?
C27 O4 C29 C11 15.3(2) . . . . ?
C27 O4 C29 C33 137.93(16) . . . . ?
C29 O4 C27 C25 -82.1(2) . . . . ?
C29 C11 C17 C12 168.93(16) . . . . ?
C29 C11 C17 C16 -83.10(19) . . . . ?
C29 C11 C17 C28 50.6(2) . . . . ?
C29 C33 C34 C28 -55.2(3) . . . . ?
C31 C12 C17 C11 91.51(16) . . . . ?
C31 C12 C17 C16 -25.60(17) . . . . ?
C31 C12 C17 C28 -152.09(15) . . . . ?
C31 C20 C36 C35 -83.2(2) . . . . ?
C35 C14 C16 C17 141.97(18) . . . . ?
C35 C14 C16 C20 30.8(2) . . . . ?
C35 C14 C16 C25 -87.3(2) . . . . ?
C36 C20 C31 C12 131.57(17) . . . . ?

_olex2_date_sample_data_collection 2019-10-16
_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_zhangy_1028
_database_code_depnum_ccdc_archive 'CCDC 1962417'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-30 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_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         'C12 H20 O2'
_chemical_formula_sum            'C12 H20 O2'
_chemical_formula_weight         196.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'pd F S C'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.1285(3)
_cell_length_b                   11.9273(4)
_cell_length_c                   13.4833(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.629(4)
_cell_angle_gamma                90
_cell_volume                     1109.23(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2260
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      69.2990
_cell_measurement_theta_min      5.0330
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4576
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.588
_diffrn_reflns_theta_max         66.588
_diffrn_reflns_theta_min         5.024
_diffrn_ambient_temperature      294.06(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   14.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   50.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00  -54.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -74.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  -19.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega   66.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   90.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   35.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
  8 omega   41.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 10 omega   92.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 13 omega   45.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 14 omega   44.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 15 omega   66.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  101.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 17 omega   71.00   97.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   47.00   83.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 40

#__ type_ start__ end____ width___ exp.time_
 20 omega   49.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega  -16.00   10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  -57.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  -65.00  -40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   81.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
 24 omega   40.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  106.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 26 omega   78.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 27 omega   53.00   78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0827620000
_diffrn_orient_matrix_UB_12      0.1160422000
_diffrn_orient_matrix_UB_13      -0.0380275000
_diffrn_orient_matrix_UB_21      0.2060353000
_diffrn_orient_matrix_UB_22      0.0419976000
_diffrn_orient_matrix_UB_23      0.0036125000
_diffrn_orient_matrix_UB_31      -0.0247053000
_diffrn_orient_matrix_UB_32      -0.0381086000
_diffrn_orient_matrix_UB_33      -0.1116959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1711
_reflns_number_total             1899
_reflns_odcompleteness_completeness 96.19
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.228
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.062
_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)+(0.0590P)²+0.2960P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1188
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.44077(17) 0.62534(9) 0.08951(8) 0.0433(3) Uani 1 1 d . . . . .
H1 H 0.412(3) 0.558(2) 0.0971(16) 0.066(6) Uiso 1 1 d . . . . .
O2 O 0.58071(19) 0.88976(9) 0.40995(8) 0.0494(3) Uani 1 1 d . . . . .
H2 H 0.533(3) 0.8780(18) 0.4585(18) 0.070(7) Uiso 1 1 d . . . . .
C1 C 0.3009(2) 0.58137(11) 0.27082(11) 0.0349(3) Uani 1 1 d . . . . .
H1A H 0.413465 0.547926 0.254469 0.042 Uiso 1 1 calc R . . . .
H1B H 0.329026 0.591966 0.344438 0.042 Uiso 1 1 calc R . . . .
C2 C 0.1238(2) 0.50517(13) 0.23447(15) 0.0509(4) Uani 1 1 d . . . . .
H2A H 0.133102 0.462047 0.174894 0.061 Uiso 1 1 calc R . . . .
H2B H 0.111613 0.453949 0.288365 0.061 Uiso 1 1 calc R . . . .
C3 C -0.0473(2) 0.58567(16) 0.20773(16) 0.0586(5) Uani 1 1 d . . . . .
H3A H -0.156718 0.552219 0.158970 0.070 Uiso 1 1 calc R . . . .
H3B H -0.087314 0.607740 0.268534 0.070 Uiso 1 1 calc R . . . .
C4 C 0.0323(2) 0.68505(14) 0.16090(13) 0.0448(4) Uani 1 1 d . . . . .
H4 H -0.040421 0.754626 0.161719 0.054 Uiso 1 1 calc R . . . .
C5 C 0.25281(19) 0.69514(11) 0.21518(10) 0.0299(3) Uani 1 1 d . . . . .
C6 C 0.2951(2) 0.69926(11) 0.10509(10) 0.0322(3) Uani 1 1 d . . . . .
C7 C 0.0837(2) 0.66283(16) 0.05830(13) 0.0518(4) Uani 1 1 d . . . . .
H7A H 0.014947 0.711054 0.003079 0.062 Uiso 1 1 calc R . . . .
H7B H 0.070974 0.584773 0.037495 0.062 Uiso 1 1 calc R . . . .
C8 C 0.3174(2) 0.79345(12) 0.28855(11) 0.0361(3) Uani 1 1 d . . . . .
H8A H 0.278564 0.862603 0.251129 0.043 Uiso 1 1 calc R . . . .
H8B H 0.248913 0.789223 0.342115 0.043 Uiso 1 1 calc R . . . .
C9 C 0.5325(2) 0.79935(12) 0.33841(11) 0.0388(4) Uani 1 1 d . . . . .
H9A H 0.574174 0.729272 0.373625 0.047 Uiso 1 1 calc R . . . .
H9B H 0.602093 0.808617 0.285716 0.047 Uiso 1 1 calc R . . . .
C10 C 0.3455(2) 0.81522(11) 0.07378(10) 0.0357(3) Uani 1 1 d . . . . .
C11 C 0.1896(3) 0.90239(16) 0.04682(15) 0.0599(5) Uani 1 1 d . . . . .
H11A H 0.109239 0.887871 -0.020597 0.090 Uiso 1 1 calc GR . . . .
H11B H 0.247701 0.975186 0.048244 0.090 Uiso 1 1 calc GR . . . .
H11C H 0.112057 0.899988 0.095543 0.090 Uiso 1 1 calc GR . . . .
C12 C 0.5248(2) 0.84009(14) 0.06955(12) 0.0427(4) Uani 1 1 d . . . . .
H12A H 0.558(3) 0.9160(16) 0.0501(14) 0.052(5) Uiso 1 1 d . . . . .
H12B H 0.625(3) 0.7847(17) 0.0879(16) 0.062(6) Uiso 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 H1 0.84(2) . ?
O1 C6 1.4178(17) . ?
O2 H2 0.82(2) . ?
O2 C9 1.4297(17) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.532(2) . ?
C1 C5 1.5465(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.519(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.5621(19) . ?
C4 C7 1.541(2) . ?
C5 C6 1.5882(18) . ?
C5 C8 1.5283(18) . ?
C6 C7 1.542(2) . ?
C6 C10 1.5155(19) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.513(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.498(2) . ?
C10 C12 1.327(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.989(19) . ?
C12 H12B 0.96(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
C6 O1 H1 111.4(15) . . ?
C9 O2 H2 109.4(16) . . ?
H1A C1 H1B 108.5 . . ?
C2 C1 H1A 110.2 . . ?
C2 C1 H1B 110.2 . . ?
C2 C1 C5 107.55(12) . . ?
C5 C1 H1A 110.2 . . ?
C5 C1 H1B 110.2 . . ?
C1 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.34(13) . . ?
C3 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 C2 103.27(13) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
C3 C4 H4 113.7 . . ?
C3 C4 C5 107.62(13) . . ?
C3 C4 C7 115.95(15) . . ?
C5 C4 H4 113.7 . . ?
C7 C4 H4 113.7 . . ?
C7 C4 C5 89.70(11) . . ?
C1 C5 C4 103.49(11) . . ?
C1 C5 C6 114.17(11) . . ?
C4 C5 C6 88.31(11) . . ?
C8 C5 C1 111.44(11) . . ?
C8 C5 C4 117.74(11) . . ?
C8 C5 C6 118.94(11) . . ?
O1 C6 C5 115.98(11) . . ?
O1 C6 C7 116.17(12) . . ?
O1 C6 C10 106.99(11) . . ?
C7 C6 C5 88.69(11) . . ?
C10 C6 C5 113.76(11) . . ?
C10 C6 C7 114.78(12) . . ?
C4 C7 C6 90.78(11) . . ?
C4 C7 H7A 113.5 . . ?
C4 C7 H7B 113.5 . . ?
C6 C7 H7A 113.5 . . ?
C6 C7 H7B 113.5 . . ?
H7A C7 H7B 110.8 . . ?
C5 C8 H8A 108.4 . . ?
C5 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C9 C8 C5 115.43(11) . . ?
C9 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
O2 C9 C8 112.26(12) . . ?
O2 C9 H9A 109.2 . . ?
O2 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C6 119.19(14) . . ?
C12 C10 C6 120.96(13) . . ?
C12 C10 C11 119.85(15) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 121.1(11) . . ?
C10 C12 H12B 119.9(12) . . ?
H12A C12 H12B 118.9(16) . . ?

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 C6 C7 C4 130.52(13) . . . . ?
O1 C6 C10 C11 158.99(14) . . . . ?
O1 C6 C10 C12 -20.71(17) . . . . ?
C1 C2 C3 C4 37.21(19) . . . . ?
C1 C5 C6 O1 -26.49(17) . . . . ?
C1 C5 C6 C7 92.17(13) . . . . ?
C1 C5 C6 C10 -151.21(12) . . . . ?
C1 C5 C8 C9 61.00(15) . . . . ?
C2 C1 C5 C4 8.79(15) . . . . ?
C2 C1 C5 C6 -85.47(14) . . . . ?
C2 C1 C5 C8 136.27(13) . . . . ?
C2 C3 C4 C5 -32.41(19) . . . . ?
C2 C3 C4 C7 66.13(19) . . . . ?
C3 C4 C5 C1 14.62(16) . . . . ?
C3 C4 C5 C6 129.09(14) . . . . ?
C3 C4 C5 C8 -108.81(15) . . . . ?
C3 C4 C7 C6 -121.74(14) . . . . ?
C4 C5 C6 O1 -130.52(12) . . . . ?
C4 C5 C6 C7 -11.86(11) . . . . ?
C4 C5 C6 C10 104.75(13) . . . . ?
C4 C5 C8 C9 -179.67(12) . . . . ?
C5 C1 C2 C3 -28.84(17) . . . . ?
C5 C4 C7 C6 -12.22(12) . . . . ?
C5 C6 C7 C4 12.02(11) . . . . ?
C5 C6 C10 C11 -71.59(17) . . . . ?
C5 C6 C10 C12 108.71(15) . . . . ?
C5 C8 C9 O2 -176.90(11) . . . . ?
C6 C5 C8 C9 -75.04(16) . . . . ?
C7 C4 C5 C1 -102.60(12) . . . . ?
C7 C4 C5 C6 11.87(11) . . . . ?
C7 C4 C5 C8 133.97(13) . . . . ?
C7 C6 C10 C11 28.52(19) . . . . ?
C7 C6 C10 C12 -151.17(14) . . . . ?
C8 C5 C6 O1 108.43(14) . . . . ?
C8 C5 C6 C7 -132.91(13) . . . . ?
C8 C5 C6 C10 -16.30(17) . . . . ?
C10 C6 C7 C4 -103.65(13) . . . . ?

_olex2_date_sample_data_collection 2019-10-28
_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_zhangye_0917
_database_code_depnum_ccdc_archive 'CCDC 1962276'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-09-18
_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         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.2165(3)
_cell_length_b                   8.3504(3)
_cell_length_c                   11.3170(4)
_cell_angle_alpha                82.649(3)
_cell_angle_beta                 76.258(3)
_cell_angle_gamma                68.964(4)
_cell_volume                     617.61(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6955
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.5970
_cell_measurement_theta_min      6.7060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11512
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        66.587
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_min         4.026
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   41.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -18.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   38.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  125.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega  -80.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   28.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   38.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega  -55.00  -21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       20.0000  160.0000  174.6694 34

#__ type_ start__ end____ width___ exp.time_
  8 omega   -8.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000  100.0000 -137.2139 25

#__ type_ start__ end____ width___ exp.time_
  9 omega    6.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.0000   85.0000   33.6144 30

#__ type_ start__ end____ width___ exp.time_
 10 omega   -2.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   96.0000   69.8149 25

#__ type_ start__ end____ width___ exp.time_
 11 omega    3.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.0000   87.0000  -94.0549 25

#__ type_ start__ end____ width___ exp.time_
 12 omega    5.00   30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   90.0000  -58.2564 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   15.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   80.0000   56.7675 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   14.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000 -145.9687 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   19.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  -39.2305 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   20.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   78.0000  109.6461 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 18 omega   30.00   66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   66.0000 -114.5049 36

#__ type_ start__ end____ width___ exp.time_
 19 omega   39.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   57.0000   58.8289 87

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   56.0000 -132.7581 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   85.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   56.0000 -132.7581 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   37.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   74.0000 -105.4160 97

#__ type_ start__ end____ width___ exp.time_
 23 omega   39.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   73.0000   -6.2651 62

#__ type_ start__ end____ width___ exp.time_
 24 omega  112.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   70.0000  133.3571 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   41.00   79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   70.0000  133.3571 38

#__ type_ start__ end____ width___ exp.time_
 26 omega   90.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   76.0000  -43.2593 57

#__ type_ start__ end____ width___ exp.time_
 27 omega  106.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   57.0000  115.9246 39

#__ type_ start__ end____ width___ exp.time_
 28 omega   55.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   57.0000  115.9246 27

#__ type_ start__ end____ width___ exp.time_
 29 omega   45.00   71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       76.0000   76.0000  -43.2593 26

#__ type_ start__ end____ width___ exp.time_
 30 omega  121.00  151.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   53.0000   66.8398 30

#__ type_ start__ end____ width___ exp.time_
 31 omega   84.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   53.0000   66.8398 27

#__ type_ start__ end____ width___ exp.time_
 32 omega  126.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   50.0000 -161.5837 32

#__ type_ start__ end____ width___ exp.time_
 33 omega  125.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   55.0000  160.2983 32

#__ type_ start__ end____ width___ exp.time_
 34 omega   66.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   50.0000 -161.5837 28

#__ type_ start__ end____ width___ exp.time_
 35 omega   66.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   55.0000  160.2983 27

#__ type_ start__ end____ width___ exp.time_
 36 omega  123.00  157.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   71.0000  -27.8578 34

#__ type_ start__ end____ width___ exp.time_
 37 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   71.0000  -27.8578 27

#__ type_ start__ end____ width___ exp.time_
 38 omega   63.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       92.0000   74.0000   37.3235 99

#__ type_ start__ end____ width___ exp.time_
 39 omega  139.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   68.0000  -31.4462 31

#__ type_ start__ end____ width___ exp.time_
 40 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   68.0000  -31.4462 26

#__ type_ start__ end____ width___ exp.time_
 41 omega  116.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0000   53.0000 -130.2669 57

#__ type_ start__ end____ width___ exp.time_
 42 omega   83.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      104.0000   53.0000 -130.2669 27

#__ type_ start__ end____ width___ exp.time_
 43 omega  114.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   76.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   78.00  164.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000    0.0000 86

#__ type_ start__ end____ width___ exp.time_
 46 omega  118.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 47 omega   76.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
 48 omega   77.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
 49 omega   76.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
 50 omega   76.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
 51 omega  130.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 52 omega   77.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 53 omega   42.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 54 omega   35.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 55 omega  108.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   80.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 57 omega  144.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 58 omega  134.00  160.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 59 omega   84.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 60 omega   42.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 61

#__ type_ start__ end____ width___ exp.time_
 61 omega  107.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 62 omega   76.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 73

#__ type_ start__ end____ width___ exp.time_
 63 omega   86.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 64 omega   43.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 65 omega   84.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 66 omega  135.00  171.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
 67 omega  153.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 68 omega   85.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
 69 omega  143.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
 70 omega   86.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
 71 omega   62.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
 72 omega  -69.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000  -30.0000 91

#__ type_ start__ end____ width___ exp.time_
 73 omega  -22.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       24.0000  104.0000  -16.5684 39

#__ type_ start__ end____ width___ exp.time_
 74 omega  -43.00  -16.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.0000  153.0000  -65.6635 27

#__ type_ start__ end____ width___ exp.time_
 75 omega   15.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   80.0000   56.7675 31

#__ type_ start__ end____ width___ exp.time_
 76 omega   14.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       48.0000   82.0000 -145.9687 31

#__ type_ start__ end____ width___ exp.time_
 77 omega   19.00   46.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000  121.4124 27

#__ type_ start__ end____ width___ exp.time_
 78 omega   18.00   45.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   82.0000  -39.2305 27

#__ type_ start__ end____ width___ exp.time_
 79 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000    0.0000 148

#__ type_ start__ end____ width___ exp.time_
 80 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -60.0000 148

#__ type_ start__ end____ width___ exp.time_
 81 omega    1.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000   30.0000 97

#__ type_ start__ end____ width___ exp.time_
 82 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -90.0000 148

#__ type_ start__ end____ width___ exp.time_
 83 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000  -30.0000 148

#__ type_ start__ end____ width___ exp.time_
 84 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -120.0000 148

#__ type_ start__ end____ width___ exp.time_
 85 omega  -20.00  128.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -180.0000 148

#__ type_ start__ end____ width___ exp.time_
 86 omega  -15.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000 -180.0000 91

#__ type_ start__ end____ width___ exp.time_
 87 omega  -20.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000    0.0000 -150.0000 125
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2013737000
_diffrn_orient_matrix_UB_12      -0.0344099000
_diffrn_orient_matrix_UB_13      0.0477476000
_diffrn_orient_matrix_UB_21      0.0260389000
_diffrn_orient_matrix_UB_22      -0.0786506000
_diffrn_orient_matrix_UB_23      -0.1213844000
_diffrn_orient_matrix_UB_31      0.1158724000
_diffrn_orient_matrix_UB_32      -0.1782891000
_diffrn_orient_matrix_UB_33      0.0516610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2021
_reflns_number_total             2182
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.284
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0447
_refine_ls_restrained_S_all      1.084
_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)+(0.0616P)²+0.2315P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1208
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C13(H13), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.12336(19) 0.09934(16) 0.39163(12) 0.0462(3) Uani 1 1 d . . . . .
O2 O -0.2227(2) 0.46409(17) 0.04267(12) 0.0520(4) Uani 1 1 d . . . . .
O3 O -0.4863(2) 0.21825(18) 0.00633(12) 0.0537(4) Uani 1 1 d . . . . .
H3 H -0.576548 0.310317 -0.001085 0.081 Uiso 1 1 calc GR . . . .
C4 C -0.1926(2) -0.02424(18) 0.24505(13) 0.0266(3) Uani 1 1 d . . . . .
C5 C -0.0730(2) 0.2363(2) 0.17480(14) 0.0323(4) Uani 1 1 d . . . . .
H5A H -0.001524 0.300169 0.200252 0.039 Uiso 1 1 calc R . . . .
H5B H 0.020393 0.162774 0.110786 0.039 Uiso 1 1 calc R . . . .
C6 C -0.2827(2) 0.0240(2) 0.13015(14) 0.0329(4) Uani 1 1 d . . . . .
H6A H -0.176713 0.035694 0.062164 0.039 Uiso 1 1 calc R . . . .
H6B H -0.318901 -0.071368 0.114613 0.039 Uiso 1 1 calc R . . . .
C7 C -0.1388(2) 0.12307(18) 0.28415(13) 0.0273(3) Uani 1 1 d . . . . .
C8 C -0.2501(2) 0.3609(2) 0.12452(14) 0.0335(4) Uani 1 1 d . . . . .
C9 C -0.4544(2) 0.3467(2) 0.17976(15) 0.0344(4) Uani 1 1 d . . . . .
H9 H -0.557619 0.448708 0.152735 0.041 Uiso 1 1 calc R . . . .
C10 C 0.0505(2) 0.0296(2) 0.33681(14) 0.0337(4) Uani 1 1 d . . . . .
C11 C -0.3067(2) 0.2454(2) 0.37420(14) 0.0336(4) Uani 1 1 d . . . . .
H11A H -0.256320 0.328334 0.396093 0.040 Uiso 1 1 calc R . . . .
H11B H -0.343687 0.180516 0.447790 0.040 Uiso 1 1 calc R . . . .
C12 C -0.3235(2) -0.0999(2) 0.34869(14) 0.0335(4) Uani 1 1 d . . . . .
H12A H -0.296188 -0.090721 0.426978 0.040 Uiso 1 1 calc R . . . .
H12B H -0.466724 -0.040321 0.350229 0.040 Uiso 1 1 calc R . . . .
C13 C -0.4675(2) 0.1865(2) 0.13049(15) 0.0358(4) Uani 1 1 d . . . . .
H13 H -0.587553 0.162553 0.178768 0.043 Uiso 1 1 calc R . . . .
C14 C 0.0115(2) -0.1779(2) 0.22225(14) 0.0332(4) Uani 1 1 d . . . . .
H14 H 0.084024 -0.171708 0.137731 0.040 Uiso 1 1 calc R . . . .
C15 C -0.4955(2) 0.3407(2) 0.32006(15) 0.0382(4) Uani 1 1 d . . . . .
H15A H -0.553085 0.457483 0.346940 0.046 Uiso 1 1 calc R . . . .
H15B H -0.595783 0.285411 0.352014 0.046 Uiso 1 1 calc R . . . .
C16 C -0.0461(3) -0.3400(2) 0.2466(2) 0.0515(5) Uani 1 1 d . . . . .
H16A H -0.037583 -0.386621 0.170442 0.062 Uiso 1 1 calc R . . . .
H16B H 0.044673 -0.426735 0.291938 0.062 Uiso 1 1 calc R . . . .
C17 C -0.2627(3) -0.2876(2) 0.3201(2) 0.0555(5) Uani 1 1 d . . . . .
H17A H -0.270171 -0.358391 0.394878 0.067 Uiso 1 1 calc R . . . .
H17B H -0.352550 -0.301067 0.273602 0.067 Uiso 1 1 calc R . . . .
C18 C 0.1322(3) -0.1561(2) 0.3089(2) 0.0524(5) Uani 1 1 d . . . . .
H18A H 0.116079 -0.226719 0.383037 0.063 Uiso 1 1 calc R . . . .
H18B H 0.275266 -0.189822 0.271106 0.063 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 C10 1.2114(19) . ?
O2 C8 1.213(2) . ?
O3 H3 0.8200 . ?
O3 C13 1.4255(19) . ?
C4 C6 1.5348(19) . ?
C4 C7 1.5568(18) . ?
C4 C12 1.543(2) . ?
C4 C14 1.558(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C7 1.547(2) . ?
C5 C8 1.510(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C13 1.523(2) . ?
C7 C10 1.5273(19) . ?
C7 C11 1.530(2) . ?
C8 C9 1.499(2) . ?
C9 H9 0.9800 . ?
C9 C13 1.554(2) . ?
C9 C15 1.542(2) . ?
C10 C18 1.494(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C15 1.536(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C17 1.523(2) . ?
C13 H13 0.9800 . ?
C14 H14 0.9800 . ?
C14 C16 1.529(2) . ?
C14 C18 1.523(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.520(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?

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
C13 O3 H3 109.5 . . ?
C6 C4 C7 112.99(12) . . ?
C6 C4 C12 111.77(12) . . ?
C6 C4 C14 110.59(12) . . ?
C7 C4 C14 105.09(11) . . ?
C12 C4 C7 113.90(12) . . ?
C12 C4 C14 101.65(11) . . ?
H5A C5 H5B 107.8 . . ?
C7 C5 H5A 109.0 . . ?
C7 C5 H5B 109.0 . . ?
C8 C5 H5A 109.0 . . ?
C8 C5 H5B 109.0 . . ?
C8 C5 C7 112.75(12) . . ?
C4 C6 H6A 107.9 . . ?
C4 C6 H6B 107.9 . . ?
H6A C6 H6B 107.2 . . ?
C13 C6 C4 117.67(12) . . ?
C13 C6 H6A 107.9 . . ?
C13 C6 H6B 107.9 . . ?
C5 C7 C4 112.85(12) . . ?
C10 C7 C4 104.03(11) . . ?
C10 C7 C5 105.60(11) . . ?
C10 C7 C11 111.85(12) . . ?
C11 C7 C4 115.58(12) . . ?
C11 C7 C5 106.57(12) . . ?
O2 C8 C5 120.08(15) . . ?
O2 C8 C9 123.42(15) . . ?
C9 C8 C5 116.49(13) . . ?
C8 C9 H9 108.1 . . ?
C8 C9 C13 108.65(13) . . ?
C8 C9 C15 111.48(13) . . ?
C13 C9 H9 108.1 . . ?
C15 C9 H9 108.1 . . ?
C15 C9 C13 112.34(13) . . ?
O1 C10 C7 123.81(15) . . ?
O1 C10 C18 125.77(15) . . ?
C18 C10 C7 110.42(13) . . ?
C7 C11 H11A 109.3 . . ?
C7 C11 H11B 109.3 . . ?
C7 C11 C15 111.58(12) . . ?
H11A C11 H11B 108.0 . . ?
C15 C11 H11A 109.3 . . ?
C15 C11 H11B 109.3 . . ?
C4 C12 H12A 110.7 . . ?
C4 C12 H12B 110.7 . . ?
H12A C12 H12B 108.8 . . ?
C17 C12 C4 105.16(13) . . ?
C17 C12 H12A 110.7 . . ?
C17 C12 H12B 110.7 . . ?
O3 C13 C6 104.49(13) . . ?
O3 C13 C9 110.30(13) . . ?
O3 C13 H13 108.8 . . ?
C6 C13 C9 115.44(12) . . ?
C6 C13 H13 108.8 . . ?
C9 C13 H13 108.8 . . ?
C4 C14 H14 110.2 . . ?
C16 C14 C4 105.86(12) . . ?
C16 C14 H14 110.2 . . ?
C18 C14 C4 104.99(12) . . ?
C18 C14 H14 110.2 . . ?
C18 C14 C16 115.22(15) . . ?
C9 C15 H15A 108.7 . . ?
C9 C15 H15B 108.7 . . ?
C11 C15 C9 114.28(13) . . ?
C11 C15 H15A 108.7 . . ?
C11 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C14 C16 H16A 110.4 . . ?
C14 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 C14 106.67(14) . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
C12 C17 H17A 110.4 . . ?
C12 C17 H17B 110.4 . . ?
C16 C17 C12 106.86(14) . . ?
C16 C17 H17A 110.4 . . ?
C16 C17 H17B 110.4 . . ?
H17A C17 H17B 108.6 . . ?
C10 C18 C14 106.72(13) . . ?
C10 C18 H18A 110.4 . . ?
C10 C18 H18B 110.4 . . ?
C14 C18 H18A 110.4 . . ?
C14 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?

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 C10 C18 C14 -171.20(16) . . . . ?
O2 C8 C9 C13 103.78(18) . . . . ?
O2 C8 C9 C15 -131.89(17) . . . . ?
C4 C6 C13 O3 167.07(13) . . . . ?
C4 C6 C13 C9 45.75(19) . . . . ?
C4 C7 C10 O1 -169.97(15) . . . . ?
C4 C7 C10 C18 11.04(17) . . . . ?
C4 C7 C11 C15 -61.98(17) . . . . ?
C4 C12 C17 C16 26.7(2) . . . . ?
C4 C14 C16 C17 -18.0(2) . . . . ?
C4 C14 C18 C10 -23.38(19) . . . . ?
C5 C7 C10 O1 70.99(19) . . . . ?
C5 C7 C10 C18 -108.00(16) . . . . ?
C5 C7 C11 C15 64.30(15) . . . . ?
C5 C8 C9 C13 -75.30(16) . . . . ?
C5 C8 C9 C15 49.03(19) . . . . ?
C6 C4 C7 C5 -31.73(17) . . . . ?
C6 C4 C7 C10 -145.70(13) . . . . ?
C6 C4 C7 C11 91.28(15) . . . . ?
C6 C4 C12 C17 81.28(16) . . . . ?
C6 C4 C14 C16 -85.29(16) . . . . ?
C6 C4 C14 C18 152.39(14) . . . . ?
C7 C4 C6 C13 -54.58(17) . . . . ?
C7 C4 C12 C17 -149.14(14) . . . . ?
C7 C4 C14 C16 152.47(13) . . . . ?
C7 C4 C14 C18 30.15(16) . . . . ?
C7 C5 C8 O2 176.18(14) . . . . ?
C7 C5 C8 C9 -4.71(19) . . . . ?
C7 C10 C18 C14 7.8(2) . . . . ?
C7 C11 C15 C9 -20.89(19) . . . . ?
C8 C5 C7 C4 76.76(16) . . . . ?
C8 C5 C7 C10 -170.23(12) . . . . ?
C8 C5 C7 C11 -51.14(16) . . . . ?
C8 C9 C13 O3 -72.61(16) . . . . ?
C8 C9 C13 C6 45.52(18) . . . . ?
C8 C9 C15 C11 -35.02(19) . . . . ?
C10 C7 C11 C15 179.24(12) . . . . ?
C11 C7 C10 O1 -44.5(2) . . . . ?
C11 C7 C10 C18 136.47(15) . . . . ?
C12 C4 C6 C13 75.46(16) . . . . ?
C12 C4 C7 C5 -160.69(12) . . . . ?
C12 C4 C7 C10 85.35(14) . . . . ?
C12 C4 C7 C11 -37.67(17) . . . . ?
C12 C4 C14 C16 33.52(15) . . . . ?
C12 C4 C14 C18 -88.80(15) . . . . ?
C13 C9 C15 C11 87.21(16) . . . . ?
C14 C4 C6 C13 -172.06(12) . . . . ?
C14 C4 C7 C5 88.93(14) . . . . ?
C14 C4 C7 C10 -25.03(14) . . . . ?
C14 C4 C7 C11 -148.05(12) . . . . ?
C14 C4 C12 C17 -36.68(16) . . . . ?
C14 C16 C17 C12 -5.2(2) . . . . ?
C15 C9 C13 O3 163.57(13) . . . . ?
C15 C9 C13 C6 -78.30(17) . . . . ?
C16 C14 C18 C10 -139.42(16) . . . . ?
C18 C14 C16 C17 97.57(19) . . . . ?

_olex2_date_sample_data_collection 2019-09-17
_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_zhangy_1021
_database_code_depnum_ccdc_archive 'CCDC 1962295'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2019-10-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H28 N2 O3 S'
_chemical_formula_sum            'C23 H28 N2 O3 S'
_chemical_formula_weight         412.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   10.3539(2)
_cell_length_b                   19.9619(4)
_cell_length_c                   11.8443(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.384(3)
_cell_angle_gamma                90.00
_cell_volume                     2246.96(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3800
_cell_measurement_temperature    295.00(10)
_cell_measurement_theta_max      69.7320
_cell_measurement_theta_min      6.5240
_exptl_absorpt_coefficient_mu    1.480
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8053
_diffrn_reflns_theta_full        66.60
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_min         4.63
_diffrn_ambient_temperature      295.00(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -22.00    4.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00  -37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000   60.0000 43

#__ type_ start__ end____ width___ exp.time_
  4 omega  -84.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega  -14.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -40.0000  -63.8281 90

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   70.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega   34.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   65.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega   51.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   54.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 39

#__ type_ start__ end____ width___ exp.time_
 11 omega   50.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   77.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   64.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 16 omega  111.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 18 omega   68.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   86.00  113.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega  136.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
 21 omega   43.00  122.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
 22 omega   50.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
 23 omega  135.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 43
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0916420000
_diffrn_orient_matrix_UB_12      -0.0558728000
_diffrn_orient_matrix_UB_13      0.0832763000
_diffrn_orient_matrix_UB_21      0.0471067000
_diffrn_orient_matrix_UB_22      0.0481803000
_diffrn_orient_matrix_UB_23      0.1107394000
_diffrn_orient_matrix_UB_31      -0.1251318000
_diffrn_orient_matrix_UB_32      -0.0227728000
_diffrn_orient_matrix_UB_33      0.0296767000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3394
_reflns_number_total             3876
_reflns_odcompleteness_completeness 97.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.234
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3876
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0621P)²+0.5554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1146
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C2(H2A,H2B), C4(H4A,H4B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19), C21(H21),
 C22(H22)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C23(H23A,H23B,
 H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.57112(5) 0.10037(2) 0.82476(4) 0.04836(16) Uani 1 d . . .
O1 O 0.36800(14) -0.07644(6) 0.79151(11) 0.0479(3) Uani 1 d . . .
O2 O 0.47148(16) 0.12597(8) 0.87015(15) 0.0723(5) Uani 1 d . . .
O3 O 0.63101(18) 0.14438(7) 0.76384(15) 0.0746(5) Uani 1 d . . .
N1 N 0.57102(13) 0.00021(6) 0.69099(11) 0.0347(3) Uani 1 d . . .
N2 N 0.48263(15) 0.04209(7) 0.72608(13) 0.0386(3) Uani 1 d . . .
H2 H 0.427(2) 0.0208(10) 0.753(2) 0.050(6) Uiso 1 d . . .
C1 C 0.50770(15) -0.04717(7) 0.61687(13) 0.0302(3) Uani 1 d . . .
C2 C 0.59543(16) -0.09708(7) 0.58526(15) 0.0349(3) Uani 1 d . . .
H2A H 0.6940 -0.0850 0.6260 0.042 Uiso 1 calc . . R
H2B H 0.5705 -0.0966 0.4972 0.042 Uiso 1 calc . . R
C3 C 0.57231(16) -0.16808(8) 0.62575(15) 0.0354(3) Uani 1 d . . .
C4 C 0.41309(15) -0.18313(7) 0.57339(15) 0.0345(3) Uani 1 d . . .
H4A H 0.3996 -0.2257 0.6068 0.041 Uiso 1 calc . . R
H4B H 0.3809 -0.1886 0.4851 0.041 Uiso 1 calc . . R
C5 C 0.31785(15) -0.13070(7) 0.59822(13) 0.0312(3) Uani 1 d . . .
C6 C 0.35227(15) -0.06125(7) 0.55908(13) 0.0308(3) Uani 1 d . . .
H6A H 0.3202 -0.0598 0.4702 0.037 Uiso 1 calc . . R
H6B H 0.3024 -0.0268 0.5836 0.037 Uiso 1 calc . . R
C7 C 0.16013(16) -0.14448(8) 0.52530(16) 0.0399(4) Uani 1 d . . .
C8 C 0.06168(19) -0.10347(10) 0.5438(2) 0.0524(5) Uani 1 d . . .
H8 H 0.0922 -0.0695 0.6022 0.063 Uiso 1 calc . . R
C9 C -0.0816(2) -0.11252(12) 0.4762(2) 0.0682(6) Uani 1 d . . .
H9 H -0.1458 -0.0847 0.4901 0.082 Uiso 1 calc . . R
C10 C -0.1291(2) -0.16174(14) 0.3899(3) 0.0834(8) Uani 1 d . . .
H10 H -0.2249 -0.1670 0.3434 0.100 Uiso 1 calc . . R
C11 C -0.0340(2) -0.20298(15) 0.3727(3) 0.0944(10) Uani 1 d . . .
H11 H -0.0659 -0.2374 0.3153 0.113 Uiso 1 calc . . R
C12 C 0.1101(2) -0.19481(11) 0.4394(2) 0.0698(7) Uani 1 d . . .
H12 H 0.1730 -0.2236 0.4257 0.084 Uiso 1 calc . . R
C13 C 0.6418(2) -0.21839(9) 0.5697(2) 0.0521(5) Uani 1 d . . .
H13A H 0.6008 -0.2143 0.4817 0.078 Uiso 1 calc . . GR
H13B H 0.6271 -0.2630 0.5925 0.078 Uiso 1 calc . . GR
H13C H 0.7409 -0.2094 0.5998 0.078 Uiso 1 calc . . GR
C14 C 0.64064(19) -0.17377(10) 0.76583(17) 0.0502(4) Uani 1 d . . .
H14A H 0.7406 -0.1683 0.7934 0.075 Uiso 1 calc . . GR
H14B H 0.6205 -0.2170 0.7904 0.075 Uiso 1 calc . . GR
H14C H 0.6037 -0.1396 0.8017 0.075 Uiso 1 calc . . GR
C15 C 0.33784(16) -0.12828(8) 0.73376(15) 0.0366(3) Uani 1 d . . .
C16 C 0.3108(2) -0.19054(10) 0.7922(2) 0.0595(5) Uani 1 d . . .
H16A H 0.3756 -0.1925 0.8768 0.089 Uiso 1 calc . . GR
H16B H 0.3233 -0.2292 0.7494 0.089 Uiso 1 calc . . GR
H16C H 0.2162 -0.1897 0.7878 0.089 Uiso 1 calc . . GR
C17 C 0.71036(18) 0.06065(9) 0.94461(15) 0.0429(4) Uani 1 d . . .
C18 C 0.68919(18) 0.00048(9) 0.99188(16) 0.0467(4) Uani 1 d . . .
H18 H 0.6019 -0.0205 0.9586 0.056 Uiso 1 calc . . R
C19 C 0.79864(19) -0.02845(11) 1.08904(17) 0.0530(5) Uani 1 d . . .
H19 H 0.7840 -0.0689 1.1209 0.064 Uiso 1 calc . . R
C20 C 0.9299(2) 0.00164(12) 1.13999(18) 0.0585(5) Uani 1 d . . .
C21 C 0.9484(2) 0.06191(14) 1.0918(2) 0.0723(7) Uani 1 d . . .
H21 H 1.0355 0.0831 1.1259 0.087 Uiso 1 calc . . R
C22 C 0.8406(2) 0.09176(11) 0.9940(2) 0.0627(5) Uani 1 d . . .
H22 H 0.8554 0.1322 0.9619 0.075 Uiso 1 calc . . R
C23 C 1.0492(2) -0.03030(16) 1.2460(2) 0.0854(8) Uani 1 d . . .
H23A H 1.0422 -0.0183 1.3219 0.128 Uiso 1 calc . . GR
H23B H 1.1373 -0.0148 1.2469 0.128 Uiso 1 calc . . GR
H23C H 1.0438 -0.0781 1.2366 0.128 Uiso 1 calc . . GR


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4335(16) . ?
S1 O3 1.4255(16) . ?
S1 N2 1.6459(13) . ?
S1 C17 1.7601(18) . ?
O1 C15 1.211(2) . ?
N1 N2 1.4181(19) . ?
N1 C1 1.2800(19) . ?
N2 H2 0.87(2) . ?
C1 C2 1.493(2) . ?
C1 C6 1.5043(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.545(2) . ?
C3 C4 1.543(2) . ?
C3 C13 1.531(2) . ?
C3 C14 1.528(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.544(2) . ?
C5 C6 1.548(2) . ?
C5 C7 1.539(2) . ?
C5 C15 1.536(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.391(2) . ?
C7 C12 1.377(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.358(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.394(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.502(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.379(3) . ?
C17 C22 1.386(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(3) . ?
C20 C21 1.377(3) . ?
C20 C23 1.509(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.385(3) . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 N2 103.75(8) . . ?
O2 S1 C17 109.83(9) . . ?
O3 S1 O2 119.51(11) . . ?
O3 S1 N2 107.91(9) . . ?
O3 S1 C17 107.72(9) . . ?
N2 S1 C17 107.53(7) . . ?
C1 N1 N2 114.97(12) . . ?
S1 N2 H2 110.6(14) . . ?
N1 N2 S1 112.50(10) . . ?
N1 N2 H2 114.5(13) . . ?
N1 C1 C2 117.92(13) . . ?
N1 C1 C6 127.90(14) . . ?
C2 C1 C6 114.14(12) . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
C1 C2 C3 110.47(12) . . ?
H2A C2 H2B 108.1 . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C4 C3 C2 109.04(12) . . ?
C13 C3 C2 108.04(13) . . ?
C13 C3 C4 107.98(13) . . ?
C14 C3 C2 110.07(14) . . ?
C14 C3 C4 112.48(13) . . ?
C14 C3 C13 109.11(14) . . ?
C3 C4 H4A 108.1 . . ?
C3 C4 H4B 108.1 . . ?
C3 C4 C5 116.92(12) . . ?
H4A C4 H4B 107.3 . . ?
C5 C4 H4A 108.1 . . ?
C5 C4 H4B 108.1 . . ?
C4 C5 C6 108.05(11) . . ?
C7 C5 C4 112.80(12) . . ?
C7 C5 C6 108.12(12) . . ?
C15 C5 C4 112.90(12) . . ?
C15 C5 C6 109.48(12) . . ?
C15 C5 C7 105.37(12) . . ?
C1 C6 C5 111.28(11) . . ?
C1 C6 H6A 109.4 . . ?
C1 C6 H6B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C5 119.16(15) . . ?
C12 C7 C5 123.32(15) . . ?
C12 C7 C8 117.50(17) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.96(19) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.9(2) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.3 . . ?
C10 C11 C12 121.4(2) . . ?
C12 C11 H11 119.3 . . ?
C7 C12 C11 120.5(2) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C5 120.98(14) . . ?
O1 C15 C16 120.01(15) . . ?
C16 C15 C5 118.90(14) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 S1 120.57(13) . . ?
C18 C17 C22 120.26(18) . . ?
C22 C17 S1 119.14(15) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.50(17) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C23 121.1(2) . . ?
C21 C20 C19 118.16(19) . . ?
C21 C20 C23 120.8(2) . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C22 121.60(19) . . ?
C22 C21 H21 119.2 . . ?
C17 C22 H22 120.4 . . ?
C21 C22 C17 119.1(2) . . ?
C21 C22 H22 120.4 . . ?
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 C17 C18 C19 -177.53(14) . . . . ?
S1 C17 C22 C21 177.22(17) . . . . ?
O2 S1 N2 N1 -166.71(11) . . . . ?
O2 S1 C17 C18 70.66(16) . . . . ?
O2 S1 C17 C22 -107.09(18) . . . . ?
O3 S1 N2 N1 65.55(13) . . . . ?
O3 S1 C17 C18 -157.67(15) . . . . ?
O3 S1 C17 C22 24.58(19) . . . . ?
N1 C1 C2 C3 119.02(14) . . . . ?
N1 C1 C6 C5 -118.41(16) . . . . ?
N2 S1 C17 C18 -41.60(17) . . . . ?
N2 S1 C17 C22 140.65(16) . . . . ?
N2 N1 C1 C2 -174.34(12) . . . . ?
N2 N1 C1 C6 3.2(2) . . . . ?
C1 N1 N2 S1 178.14(11) . . . . ?
C1 C2 C3 C4 52.19(16) . . . . ?
C1 C2 C3 C13 169.31(13) . . . . ?
C1 C2 C3 C14 -71.64(16) . . . . ?
C2 C1 C6 C5 59.17(16) . . . . ?
C2 C3 C4 C5 -51.82(17) . . . . ?
C3 C4 C5 C6 51.26(17) . . . . ?
C3 C4 C5 C7 170.73(13) . . . . ?
C3 C4 C5 C15 -69.95(17) . . . . ?
C4 C5 C6 C1 -51.80(15) . . . . ?
C4 C5 C7 C8 176.41(15) . . . . ?
C4 C5 C7 C12 -5.2(2) . . . . ?
C4 C5 C15 O1 124.33(16) . . . . ?
C4 C5 C15 C16 -59.36(19) . . . . ?
C5 C7 C8 C9 177.39(18) . . . . ?
C5 C7 C12 C11 -177.3(2) . . . . ?
C6 C1 C2 C3 -58.82(16) . . . . ?
C6 C5 C7 C8 -64.17(19) . . . . ?
C6 C5 C7 C12 114.2(2) . . . . ?
C6 C5 C15 O1 3.9(2) . . . . ?
C6 C5 C15 C16 -179.76(14) . . . . ?
C7 C5 C6 C1 -174.18(12) . . . . ?
C7 C5 C15 O1 -112.13(16) . . . . ?
C7 C5 C15 C16 64.18(18) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C7 C12 C11 1.0(4) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C9 C10 C11 C12 -1.5(5) . . . . ?
C10 C11 C12 C7 0.3(5) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C13 C3 C4 C5 -168.98(14) . . . . ?
C14 C3 C4 C5 70.57(17) . . . . ?
C15 C5 C6 C1 71.52(15) . . . . ?
C15 C5 C7 C8 52.82(19) . . . . ?
C15 C5 C7 C12 -128.8(2) . . . . ?
C17 S1 N2 N1 -50.39(13) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C22 C21 -0.5(3) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C18 C19 C20 C23 -179.9(2) . . . . ?
C19 C20 C21 C22 -1.0(4) . . . . ?
C20 C21 C22 C17 1.0(4) . . . . ?
C22 C17 C18 C19 0.2(3) . . . . ?
C23 C20 C21 C22 179.5(2) . . . . ?

_olex2_date_sample_data_collection 2019-10-21
_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_zhangy_0518
_database_code_depnum_ccdc_archive 'CCDC 1962296'
loop_
_audit_author_name
_audit_author_address
'YE ZHANG'
;LANZHOU UNIVERSITY
China
;
_audit_update_record             
;
2019-10-29 deposited with the CCDC.	2020-03-11 downloaded from the CCDC.
;
_audit_creation_date             2018-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H30 N2 O4 S'
_chemical_formula_sum            'C22 H30 N2 O4 S'
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.9610(3)
_cell_length_b                   17.5295(6)
_cell_length_c                   13.2899(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.667(3)
_cell_angle_gamma                90.00
_cell_volume                     2272.62(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2956
_cell_measurement_temperature    295.3(2)
_cell_measurement_theta_max      69.6190
_cell_measurement_theta_min      5.0230
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7941
_diffrn_reflns_theta_full        66.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_min         4.23
_diffrn_ambient_temperature      295.3(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000   57.0000 -150.0000 64

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00  -44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000 -120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -76.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.5000  178.0000  -30.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   32.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -60.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  6 omega  102.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  146.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00  139.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 100

#__ type_ start__ end____ width___ exp.time_
  9 omega  116.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -60.0000 61

#__ type_ start__ end____ width___ exp.time_
 10 omega   35.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega   35.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   35.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   63.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   57.00   94.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 16 omega  115.00  166.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00   88.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1564485000
_diffrn_orient_matrix_UB_12      0.0066793000
_diffrn_orient_matrix_UB_13      0.0105267000
_diffrn_orient_matrix_UB_21      0.0102671000
_diffrn_orient_matrix_UB_22      0.0408583000
_diffrn_orient_matrix_UB_23      0.1039223000
_diffrn_orient_matrix_UB_31      0.0188890000
_diffrn_orient_matrix_UB_32      -0.0774888000
_diffrn_orient_matrix_UB_33      0.0557221000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3232
_reflns_number_total             3890
_reflns_odcompleteness_completeness 96.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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         0.856
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         3890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0565
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0918P)²+1.0790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1700
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_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:
 C3(H3), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C22(H22A,H22B,
 H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S1 S 0.19798(6) 0.06550(4) 0.06891(5) 0.0487(2) Uani 1 d . . .
O1 O 0.3350(3) 0.38673(14) 0.05356(18) 0.0790(7) Uani 1 d . . .
O2 O 0.2883(4) 0.50154(17) -0.0164(3) 0.1106(11) Uani 1 d . . .
O3 O 0.2791(2) 0.10408(12) 0.15388(14) 0.0653(6) Uani 1 d . . .
O4 O 0.1458(2) -0.00917(11) 0.08445(15) 0.0608(5) Uani 1 d . . .
N1 N 0.0876(2) 0.19033(11) -0.00272(15) 0.0463(5) Uani 1 d . . .
N2 N 0.0599(2) 0.11582(13) 0.02616(18) 0.0502(5) Uani 1 d . . .
H2 H 0.004(3) 0.0937(17) -0.008(2) 0.048(8) Uiso 1 d . . .
C1 C 0.0027(3) 0.30572(15) -0.09641(19) 0.0476(6) Uani 1 d . . .
C2 C 0.0509(3) 0.30452(16) -0.1993(2) 0.0550(6) Uani 1 d . . .
H2A H -0.0099 0.2720 -0.2471 0.066 Uiso 1 calc . . R
H2B H 0.0443 0.3557 -0.2277 0.066 Uiso 1 calc . . R
C3 C 0.1978(3) 0.27602(18) -0.1895(2) 0.0605(7) Uani 1 d . . .
H3 H 0.1995 0.2219 -0.1710 0.073 Uiso 1 calc . . R
C4 C 0.2900(3) 0.31830(19) -0.1029(3) 0.0676(8) Uani 1 d . . .
H4 H 0.3835 0.3202 -0.1021 0.081 Uiso 1 calc . . R
C5 C 0.2434(3) 0.35223(17) -0.0293(2) 0.0599(7) Uani 1 d . . .
C6 C 0.0980(3) 0.35525(16) -0.0184(2) 0.0554(6) Uani 1 d . . .
H6A H 0.0666 0.4077 -0.0261 0.066 Uiso 1 calc . . R
H6B H 0.0925 0.3387 0.0504 0.066 Uiso 1 calc . . R
C7 C -0.1469(3) 0.33261(17) -0.1119(2) 0.0604(7) Uani 1 d . . .
H7A H -0.1683 0.3488 -0.0472 0.072 Uiso 1 calc . . R
H7B H -0.1632 0.3749 -0.1599 0.072 Uiso 1 calc . . R
C8 C -0.2337(3) 0.26370(19) -0.1548(3) 0.0684(8) Uani 1 d . . .
H8A H -0.2446 0.2610 -0.2289 0.082 Uiso 1 calc . . R
H8B H -0.3237 0.2663 -0.1376 0.082 Uiso 1 calc . . R
C9 C -0.1529(3) 0.19450(18) -0.1031(2) 0.0622(7) Uani 1 d . . .
H9A H -0.1938 0.1750 -0.0479 0.075 Uiso 1 calc . . R
H9B H -0.1511 0.1540 -0.1525 0.075 Uiso 1 calc . . R
C10 C -0.0103(3) 0.22404(14) -0.06169(18) 0.0455(5) Uani 1 d . . .
C11 C 0.2409(4) 0.2827(2) -0.2953(3) 0.0806(10) Uani 1 d . . .
H11 H 0.2153 0.3337 -0.3228 0.097 Uiso 1 calc . . R
C12 C 0.3871(5) 0.2725(4) -0.2915(4) 0.1240(19) Uani 1 d . . .
H12A H 0.4350 0.3185 -0.2671 0.186 Uiso 1 calc . . GR
H12B H 0.4018 0.2609 -0.3590 0.186 Uiso 1 calc . . GR
H12C H 0.4207 0.2312 -0.2458 0.186 Uiso 1 calc . . GR
C13 C 0.1624(5) 0.2244(3) -0.3702(3) 0.1143(18) Uani 1 d . . .
H13A H 0.1934 0.1739 -0.3490 0.171 Uiso 1 calc . . GR
H13B H 0.1784 0.2341 -0.4379 0.171 Uiso 1 calc . . GR
H13C H 0.0662 0.2285 -0.3708 0.171 Uiso 1 calc . . GR
C14 C 0.3447(4) 0.4632(2) 0.0535(3) 0.0803(10) Uani 1 d . . .
C15 C 0.4332(5) 0.4912(3) 0.1507(3) 0.1085(15) Uani 1 d . . .
H15A H 0.3847 0.4866 0.2059 0.163 Uiso 1 calc . . GR
H15B H 0.4562 0.5437 0.1427 0.163 Uiso 1 calc . . GR
H15C H 0.5156 0.4613 0.1659 0.163 Uiso 1 calc . . GR
C16 C 0.2910(3) 0.06110(14) -0.0302(2) 0.0469(6) Uani 1 d . . .
C17 C 0.4148(3) 0.09823(18) -0.0197(2) 0.0638(7) Uani 1 d . . .
H17 H 0.4501 0.1255 0.0398 0.077 Uiso 1 calc . . R
C18 C 0.4854(3) 0.0946(2) -0.0979(3) 0.0724(9) Uani 1 d . . .
H18 H 0.5694 0.1194 -0.0901 0.087 Uiso 1 calc . . R
C19 C 0.4363(3) 0.05549(18) -0.1878(2) 0.0628(7) Uani 1 d . . .
C20 C 0.3121(3) 0.0182(2) -0.1966(2) 0.0701(8) Uani 1 d . . .
H20 H 0.2768 -0.0087 -0.2564 0.084 Uiso 1 calc . . R
C21 C 0.2395(3) 0.02023(18) -0.1185(2) 0.0632(7) Uani 1 d . . .
H21 H 0.1567 -0.0057 -0.1252 0.076 Uiso 1 calc . . R
C22 C 0.5145(4) 0.0521(2) -0.2734(3) 0.0889(11) Uani 1 d . . .
H22A H 0.5664 0.0056 -0.2683 0.133 Uiso 1 calc . . GR
H22B H 0.5757 0.0949 -0.2682 0.133 Uiso 1 calc . . GR
H22C H 0.4514 0.0537 -0.3384 0.133 Uiso 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 O3 1.4202(19) . ?
S1 O4 1.4388(19) . ?
S1 N2 1.636(2) . ?
S1 C16 1.758(3) . ?
O1 C5 1.416(3) . ?
O1 C14 1.344(5) . ?
O2 C14 1.191(5) . ?
N1 N2 1.404(3) . ?
N1 C10 1.267(3) . ?
N2 H2 0.75(3) . ?
C1 C2 1.538(3) . ?
C1 C6 1.528(4) . ?
C1 C7 1.536(4) . ?
C1 C10 1.518(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.526(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.513(4) . ?
C3 C11 1.555(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.308(4) . ?
C5 C6 1.486(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.527(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.539(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.458(5) . ?
C11 C13 1.527(5) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.492(5) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.377(4) . ?
C16 C21 1.382(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.368(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.379(5) . ?
C19 C20 1.383(5) . ?
C19 C22 1.505(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(4) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
O3 S1 O4 118.90(12) . . ?
O3 S1 N2 108.84(13) . . ?
O3 S1 C16 108.36(13) . . ?
O4 S1 N2 103.72(12) . . ?
O4 S1 C16 109.15(13) . . ?
N2 S1 C16 107.28(11) . . ?
C14 O1 C5 117.4(3) . . ?
C10 N1 N2 115.7(2) . . ?
S1 N2 H2 114(2) . . ?
N1 N2 S1 113.47(17) . . ?
N1 N2 H2 118(2) . . ?
C6 C1 C2 110.4(2) . . ?
C6 C1 C7 111.7(2) . . ?
C7 C1 C2 110.7(2) . . ?
C10 C1 C2 108.6(2) . . ?
C10 C1 C6 114.1(2) . . ?
C10 C1 C7 101.0(2) . . ?
C1 C2 H2A 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.3(2) . . ?
C3 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C2 C3 H3 107.8 . . ?
C2 C3 C11 109.5(3) . . ?
C4 C3 C2 109.2(2) . . ?
C4 C3 H3 107.8 . . ?
C4 C3 C11 114.5(3) . . ?
C11 C3 H3 107.8 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.7(3) . . ?
C5 C4 H4 118.7 . . ?
O1 C5 C6 113.3(3) . . ?
C4 C5 O1 120.4(3) . . ?
C4 C5 C6 126.1(3) . . ?
C1 C6 H6A 108.9 . . ?
C1 C6 H6B 108.9 . . ?
C5 C6 C1 113.5(2) . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C1 C7 H7A 110.6 . . ?
C1 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C8 C7 C1 105.6(2) . . ?
C8 C7 H7A 110.6 . . ?
C8 C7 H7B 110.6 . . ?
C7 C8 H8A 110.8 . . ?
C7 C8 H8B 110.8 . . ?
C7 C8 C9 104.5(2) . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 H8A 110.8 . . ?
C9 C8 H8B 110.8 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 C8 105.2(2) . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N1 C10 C1 121.7(2) . . ?
N1 C10 C9 128.0(2) . . ?
C9 C10 C1 110.2(2) . . ?
C3 C11 H11 107.9 . . ?
C12 C11 C3 114.6(4) . . ?
C12 C11 H11 107.9 . . ?
C12 C11 C13 108.4(4) . . ?
C13 C11 C3 109.9(3) . . ?
C13 C11 H11 107.9 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 C15 110.9(4) . . ?
O2 C14 O1 122.7(3) . . ?
O2 C14 C15 126.3(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 S1 120.1(2) . . ?
C17 C16 C21 120.1(3) . . ?
C21 C16 S1 119.8(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.3(3) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 118.9 . . ?
C17 C18 C19 122.2(3) . . ?
C19 C18 H18 118.9 . . ?
C18 C19 C20 117.6(3) . . ?
C18 C19 C22 121.8(3) . . ?
C20 C19 C22 120.6(3) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.3(3) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 120.3 . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 H21 120.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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 C16 C17 C18 -179.6(2) . . . . ?
S1 C16 C21 C20 178.9(2) . . . . ?
O1 C5 C6 C1 -169.3(2) . . . . ?
O3 S1 N2 N1 57.5(2) . . . . ?
O3 S1 C16 C17 -5.7(3) . . . . ?
O3 S1 C16 C21 174.2(2) . . . . ?
O4 S1 N2 N1 -174.94(18) . . . . ?
O4 S1 C16 C17 -136.6(2) . . . . ?
O4 S1 C16 C21 43.4(3) . . . . ?
N2 S1 C16 C17 111.6(2) . . . . ?
N2 S1 C16 C21 -68.4(2) . . . . ?
N2 N1 C10 C1 177.8(2) . . . . ?
N2 N1 C10 C9 1.1(4) . . . . ?
C1 C2 C3 C4 -49.7(3) . . . . ?
C1 C2 C3 C11 -175.7(2) . . . . ?
C1 C7 C8 C9 33.8(3) . . . . ?
C2 C1 C6 C5 -34.1(3) . . . . ?
C2 C1 C7 C8 78.3(3) . . . . ?
C2 C1 C10 N1 92.6(3) . . . . ?
C2 C1 C10 C9 -90.1(3) . . . . ?
C2 C3 C4 C5 21.3(4) . . . . ?
C2 C3 C11 C12 167.8(4) . . . . ?
C2 C3 C11 C13 -69.8(4) . . . . ?
C3 C4 C5 O1 175.8(3) . . . . ?
C3 C4 C5 C6 -0.2(5) . . . . ?
C4 C3 C11 C12 44.8(5) . . . . ?
C4 C3 C11 C13 167.2(3) . . . . ?
C4 C5 C6 C1 6.9(5) . . . . ?
C5 O1 C14 O2 -6.0(6) . . . . ?
C5 O1 C14 C15 173.9(3) . . . . ?
C6 C1 C2 C3 57.5(3) . . . . ?
C6 C1 C7 C8 -158.2(2) . . . . ?
C6 C1 C10 N1 -31.0(3) . . . . ?
C6 C1 C10 C9 146.3(2) . . . . ?
C7 C1 C2 C3 -178.3(2) . . . . ?
C7 C1 C6 C5 -157.7(2) . . . . ?
C7 C1 C10 N1 -151.0(2) . . . . ?
C7 C1 C10 C9 26.3(3) . . . . ?
C7 C8 C9 C10 -16.8(3) . . . . ?
C8 C9 C10 N1 170.8(3) . . . . ?
C8 C9 C10 C1 -6.2(3) . . . . ?
C10 N1 N2 S1 160.96(19) . . . . ?
C10 C1 C2 C3 -68.3(3) . . . . ?
C10 C1 C6 C5 88.5(3) . . . . ?
C10 C1 C7 C8 -36.5(3) . . . . ?
C11 C3 C4 C5 144.4(4) . . . . ?
C14 O1 C5 C4 103.9(4) . . . . ?
C14 O1 C5 C6 -79.7(4) . . . . ?
C16 S1 N2 N1 -59.5(2) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C17 C16 C21 C20 -1.2(4) . . . . ?
C17 C18 C19 C20 -0.9(5) . . . . ?
C17 C18 C19 C22 179.8(3) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C16 0.8(5) . . . . ?
C21 C16 C17 C18 0.5(4) . . . . ?
C22 C19 C20 C21 179.5(3) . . . . ?

_olex2_date_sample_data_collection 2018-05-18
_olex2_submission_special_instructions 'No special instructions were received'
