# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_exp_1472
_database_code_depnum_ccdc_archive 'CCDC 2053552'
loop_
_audit_author_name
_audit_author_address
'Xiaoli Zhao'
;East China Normal University
China
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2021-01-03
_audit_creation_method           
;
Olex2 1.3-beta
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_chemical_formula_moiety         'C15 H20 Cl N O3'
_chemical_formula_sum            'C15 H20 Cl N O3'
_chemical_formula_weight         297.783
_chemical_absolute_configuration unk
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   9.5536(1)
_cell_length_b                   10.5647(1)
_cell_length_c                   15.0670(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1520.73(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27717
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      74.1260
_cell_measurement_theta_min      4.6510
_exptl_absorpt_coefficient_mu    2.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.301
_exptl_crystal_description       block
_exptl_crystal_F_000             635.363
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.9944
_diffrn_reflns_Laue_measured_fraction_max 0.9944
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            36528
_diffrn_reflns_point_group_measured_fraction_full 0.9949
_diffrn_reflns_point_group_measured_fraction_max 0.9926
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.50
_diffrn_reflns_theta_min         5.11
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.9944
_diffrn_measured_fraction_theta_max 0.9944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  76.00   1.00    1.00    --    0.00  38.00 -90.00   41
  2  ω     60.00  85.00   1.00    1.00    --    0.00  19.00 120.00   25
  3  ω     53.00  84.00   1.00    1.00    --    0.00  77.00-180.00   31
  4  ω    -16.00  20.00   1.00    1.00    --    0.00 -57.00 -90.00   36
  5  ω      8.00  66.00   1.00    1.00    --    0.00  82.00  30.00   58
  6  ω     52.00  78.00   1.00    1.00    --    0.00  38.00   0.00   26
  7  ω    -18.00  49.00   1.00    1.00    --    0.00  38.00   0.00   67
  8  ω    -30.00  -3.00   1.00    1.00    --    0.00  82.00  30.00   27
  9  ω    -84.00 -41.00   1.00    1.00    --    0.00 -57.00 -90.00   43
 10  ω     -9.00  25.00   1.00    1.00    --    0.00  38.00 -90.00   34
 11  ω    -22.00  46.00   1.00    1.00    --    0.00  19.00 120.00   68
 12  ω     29.00  81.00   1.00    1.00    --    0.00  38.00 150.00   52
 13  ω    -29.00   8.00   1.00    1.00    --    0.00  77.00-180.00   37
 14  ω    -19.00  21.00   1.00    1.00    --    0.00  38.00 150.00   40
 15  ω     65.00  90.00   1.00    1.00    --   95.80  82.00 150.00   25
 16  ω     26.00 128.00   1.00    1.00    --   95.80 -82.00-150.00  102
 17  ω     73.00 115.00   1.00    1.00    --   95.80  55.00 135.18   42
 18  ω     81.00 127.00   1.00    1.00    --   95.80 -82.00  60.00   46
 19  ω     64.00 110.00   1.00    1.00    --   95.80 -61.00-150.00   46
 20  ω     69.00  95.00   1.00    1.00    --   95.80  66.00   6.49   26
 21  ω     72.00 121.00   1.00    1.00    --   95.80  59.00   7.14   49
 22  ω     63.00  94.00   1.00    1.00    --   95.80  82.00-180.00   31
 23  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-120.00   26
 24  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -90.00   26
 25  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 26  ω     75.00 168.00   1.00    1.00    --   95.80  45.00-120.00   93
 27  ω     72.00 185.00   1.00    1.00    --   95.80  61.00 -90.00  113
 28  ω     67.00  93.00   1.00    1.00    --   95.80  82.00-120.00   26
 29  ω     65.00  93.00   1.00    1.00    --   95.80  77.00 120.00   28
 30  ω      6.00 117.00   1.00    1.00    --   95.80 -61.00   0.00  111
 31  ω     71.00  97.00   1.00    1.00    --   95.80  61.00-120.00   26
 32  ω     66.00  91.00   1.00    1.00    --   95.80  77.00 -30.00   25
 33  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 34  ω    126.00 170.00   1.00    1.00    --   95.80  82.00 -60.00   44
 35  ω    143.00 182.00   1.00    1.00    --   95.80  59.00-102.36   39
 36  ω    143.00 169.00   1.00    1.00    --   95.80  74.00  84.62   26
 37  ω     72.00 114.00   1.00    1.00    --   95.80  61.00 -60.00   42
 38  ω     75.00 173.00   1.00    1.00    --   95.80  45.00   0.00   98
 39  ω     71.00 184.00   1.00    1.00    --   95.80  61.00  90.00  113
 40  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 41  ω      8.00  34.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 42  ω     41.00 128.00   1.00    1.00    --   95.80 -82.00 -60.00   87
 43  ω     64.00  90.00   1.00    1.00    --   95.80  82.00 -60.00   26
 44  ω     75.00 185.00   1.00    1.00    --   95.80  45.00-150.00  110
 45  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 150.00   25
 46  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-180.00   25
 47  ω      8.00 127.00   1.00    1.00    --   95.80 -82.00   0.00  119
 48  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  90.00   25
 49  ω     63.00  99.00   1.00    1.00    --   95.80  82.00 120.00   36
 50  ω     75.00 133.00   1.00    1.00    --   95.80  45.00  90.00   58
 51  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 52  ω     77.00 103.00   1.00    1.00    --   95.80  45.00-180.00   26
 53  ω     72.00  98.00   1.00    1.00    --   95.80  59.00-102.36   26
 54  ω     75.00 154.00   1.00    1.00    --   95.80  45.00  60.00   79
 55  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 56  ω     65.00  91.00   1.00    1.00    --   95.80  82.00   0.00   26
 57  ω    110.00 184.00   1.00    1.00    --   95.80  82.00   0.00   74
 58  ω     63.00  88.00   1.00    1.00    --   95.80  82.00  30.00   25
 59  ω     38.00 109.00   1.00    1.00    --   95.80 -82.00 150.00   71
 60  ω     76.00 160.00   1.00    1.00    --   95.80  30.00-180.00   84
 61  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  90.00   26
 62  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 63  ω    120.00 145.00   1.00    1.00    --   95.80  55.00 135.18   25
 64  ω     66.00  91.00   1.00    1.00    --   95.80  74.00  84.62   25
 65  ω    119.00 185.00   1.00    1.00    --   95.80  43.00 -21.36   66
 66  ω     75.00 111.00   1.00    1.00    --   95.80  43.00 -21.36   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239517000
_diffrn_orient_matrix_UB_12      0.1388604000
_diffrn_orient_matrix_UB_13      0.0271592000
_diffrn_orient_matrix_UB_21      0.0343540000
_diffrn_orient_matrix_UB_22      -0.0427710000
_diffrn_orient_matrix_UB_23      0.0952586000
_diffrn_orient_matrix_UB_31      0.1558136000
_diffrn_orient_matrix_UB_32      -0.0119397000
_diffrn_orient_matrix_UB_33      -0.0252178000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.990
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              18
_reflns_limit_l_min              -18
_reflns_number_gt                3063
_reflns_number_total             3079
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.3-beta (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.1329
_refine_diff_density_min         -0.2676
_refine_diff_density_rms         0.0342
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.017(9)
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             8.6501
_refine_ls_goodness_of_fit_ref   1.0359
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3079
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0228
_refine_ls_restrained_S_all      1.0359
_refine_ls_shift/su_max          0.0054
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0314P)²+0.3555P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0586
_refine_ls_wR_factor_ref         0.0587
_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:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C7(H7a,H7b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C1(H1)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Cl1 Cl 0.68684(3) 0.25797(3) 0.44026(2) 0.02932(8) Uani 1.000000 .
O3 O 0.39708(9) 0.75511(8) 0.66140(5) 0.02109(17) Uani 1.000000 .
O2 O 0.56993(9) 0.63096(8) 0.60332(5) 0.02118(18) Uani 1.000000 .
O1 O 0.39537(9) 0.88865(8) 0.51231(6) 0.02011(18) Uani 1.000000 .
N1 N 0.46197(10) 0.76880(9) 0.51500(6) 0.0161(2) Uani 1.000000 .
C11 C 0.47238(12) 0.72174(10) 0.60132(8) 0.0157(2) Uani 1.000000 .
C8 C 0.58227(12) 0.77521(10) 0.45329(7) 0.0166(2) Uani 1.000000 .
H8 H 0.66216(12) 0.72855(10) 0.47766(7) 0.0199(3) Uiso 1.000000 R
C6 C 0.50157(13) 0.58173(11) 0.36731(7) 0.0185(2) Uani 1.000000 .
C5 C 0.59916(13) 0.49403(11) 0.39830(8) 0.0190(2) Uani 1.000000 .
H5 H 0.68742(13) 0.52052(11) 0.41656(8) 0.0229(3) Uiso 1.000000 R
C4 C 0.56324(13) 0.36692(11) 0.40159(8) 0.0203(2) Uani 1.000000 .
C9 C 0.61616(13) 0.91842(11) 0.44840(8) 0.0210(2) Uani 1.000000 .
H9a H 0.71127(13) 0.93522(11) 0.46761(8) 0.0252(3) Uiso 1.000000 R
H9b H 0.60386(13) 0.95052(11) 0.38858(8) 0.0252(3) Uiso 1.000000 R
C7 C 0.54051(13) 0.72059(11) 0.36320(7) 0.0191(2) Uani 1.000000 .
H7a H 0.46154(13) 0.76809(11) 0.34023(7) 0.0229(3) Uiso 1.000000 R
H7b H 0.61781(13) 0.73116(11) 0.32212(7) 0.0229(3) Uiso 1.000000 R
C12 C 0.57600(13) 0.54046(11) 0.67842(7) 0.0190(2) Uani 1.000000 .
C14 C 0.44232(15) 0.46389(13) 0.67969(10) 0.0282(3) Uani 1.000000 .
H14a H 0.3644(2) 0.5190(2) 0.6909(7) 0.0423(4) Uiso 1.000000 GR
H14b H 0.4300(6) 0.4230(9) 0.6233(3) 0.0423(4) Uiso 1.000000 GR
H14c H 0.4477(5) 0.4011(7) 0.7256(5) 0.0423(4) Uiso 1.000000 GR
C10 C 0.51061(14) 0.97690(12) 0.51164(9) 0.0237(3) Uani 1.000000 .
H10a H 0.48056(14) 1.05930(12) 0.49058(9) 0.0285(3) Uiso 1.000000 R
H10b H 0.55021(14) 0.98616(12) 0.57056(9) 0.0285(3) Uiso 1.000000 R
C13 C 0.60313(15) 0.60931(13) 0.76519(8) 0.0251(3) Uani 1.000000 .
H13a H 0.6818(7) 0.6649(7) 0.7583(2) 0.0377(4) Uiso 1.000000 GR
H13b H 0.5220(4) 0.6578(8) 0.7811(4) 0.0377(4) Uiso 1.000000 GR
H13c H 0.6228(11) 0.54873(13) 0.81102(18) 0.0377(4) Uiso 1.000000 GR
C3 C 0.43303(15) 0.32342(12) 0.37534(9) 0.0265(3) Uani 1.000000 .
H3 H 0.41103(15) 0.23775(12) 0.37796(9) 0.0318(3) Uiso 1.000000 R
C2 C 0.33652(15) 0.41101(14) 0.34510(10) 0.0320(3) Uani 1.000000 .
H2 H 0.24818(15) 0.38408(14) 0.32735(10) 0.0384(4) Uiso 1.000000 R
C15 C 0.70124(16) 0.45867(13) 0.65493(9) 0.0290(3) Uani 1.000000 .
H15a H 0.6858(5) 0.4191(8) 0.5984(4) 0.0435(4) Uiso 1.000000 GR
H15b H 0.7837(3) 0.5104(2) 0.6520(7) 0.0435(4) Uiso 1.000000 GR
H15c H 0.7135(7) 0.3947(7) 0.6995(4) 0.0435(4) Uiso 1.000000 GR
C1 C 0.37030(14) 0.53891(13) 0.34099(9) 0.0269(3) Uani 1.000000 .
H1 H 0.30428(14) 0.59655(13) 0.32039(9) 0.0323(3) Uiso 1.000000 R


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
Cl1 C4 1.7489(13) . ?
O3 C11 1.2088(14) . ?
O2 C11 1.3376(13) . ?
O2 C12 1.4824(13) . ?
O1 N1 1.4176(12) . ?
O1 C10 1.4428(15) . ?
N1 C11 1.3959(14) . ?
N1 C8 1.4799(14) . ?
C8 H8 0.9800 . ?
C8 C9 1.5490(15) . ?
C8 C7 1.5279(15) . ?
C6 C5 1.3949(17) . ?
C6 C7 1.5147(16) . ?
C6 C1 1.3909(18) . ?
C5 H5 0.9300 . ?
C5 C4 1.3869(17) . ?
C4 C3 1.3838(18) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C9 C10 1.5187(17) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C12 C14 1.5119(18) . ?
C12 C13 1.5184(16) . ?
C12 C15 1.5177(17) . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C3 H3 0.9300 . ?
C3 C2 1.383(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.391(2) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C1 H1 0.9300 . ?

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
C12 O2 C11 120.46(9) . . ?
C10 O1 N1 103.58(8) . . ?
C11 N1 O1 112.14(8) . . ?
C8 N1 O1 106.84(8) . . ?
C8 N1 C11 123.12(9) . . ?
O2 C11 O3 127.36(10) . . ?
N1 C11 O3 123.46(10) . . ?
N1 C11 O2 109.03(9) . . ?
H8 C8 N1 110.26(6) . . ?
C9 C8 N1 103.70(9) . . ?
C9 C8 H8 110.26(6) . . ?
C7 C8 N1 109.76(9) . . ?
C7 C8 H8 110.26(6) . . ?
C7 C8 C9 112.41(9) . . ?
C7 C6 C5 119.52(11) . . ?
C1 C6 C5 118.82(11) . . ?
C1 C6 C7 121.66(11) . . ?
H5 C5 C6 120.34(7) . . ?
C4 C5 C6 119.32(11) . . ?
C4 C5 H5 120.34(7) . . ?
C5 C4 Cl1 118.82(10) . . ?
C3 C4 Cl1 118.92(10) . . ?
C3 C4 C5 122.26(12) . . ?
H9a C9 C8 111.12(6) . . ?
H9b C9 C8 111.12(6) . . ?
H9b C9 H9a 109.1 . . ?
C10 C9 C8 103.22(9) . . ?
C10 C9 H9a 111.12(7) . . ?
C10 C9 H9b 111.12(7) . . ?
C6 C7 C8 113.18(9) . . ?
H7a C7 C8 108.94(6) . . ?
H7a C7 C6 108.94(7) . . ?
H7b C7 C8 108.94(6) . . ?
H7b C7 C6 108.94(6) . . ?
H7b C7 H7a 107.8 . . ?
C14 C12 O2 108.76(10) . . ?
C13 C12 O2 110.79(9) . . ?
C13 C12 C14 112.93(11) . . ?
C15 C12 O2 102.71(9) . . ?
C15 C12 C14 111.37(11) . . ?
C15 C12 C13 109.81(11) . . ?
H14a C14 C12 109.5 . . ?
H14b C14 C12 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C12 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C9 C10 O1 104.37(10) . . ?
H10a C10 O1 110.88(6) . . ?
H10a C10 C9 110.88(7) . . ?
H10b C10 O1 110.88(6) . . ?
H10b C10 C9 110.88(7) . . ?
H10b C10 H10a 108.9 . . ?
H13a C13 C12 109.5 . . ?
H13b C13 C12 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C12 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H3 C3 C4 120.95(8) . . ?
C2 C3 C4 118.10(12) . . ?
C2 C3 H3 120.95(8) . . ?
H2 C2 C3 119.67(8) . . ?
C1 C2 C3 120.66(13) . . ?
C1 C2 H2 119.67(8) . . ?
H15a C15 C12 109.5 . . ?
H15b C15 C12 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C12 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
C2 C1 C6 120.84(13) . . ?
H1 C1 C6 119.58(8) . . ?
H1 C1 C2 119.58(8) . . ?


_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 2.440
_oxdiff_exptl_absorpt_empirical_full_min 0.667
####################################################################### 
# 
# 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_exp_1513
_database_code_depnum_ccdc_archive 'CCDC 2053557'
loop_
_audit_author_name
_audit_author_address
'Xiaoli Zhao'
;East China Normal University
China
;
_audit_update_record             
;
2021-01-03 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_audit_creation_date             2020-10-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H68 N O3 P S'
_chemical_formula_sum            'C42 H68 N O3 P S'
_chemical_formula_weight         698.00
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
P P 0.2955 0.4335 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   13.71390(10)
_cell_length_b                   14.69290(10)
_cell_length_c                   20.80280(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4191.70(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    51263
_cell_measurement_temperature    100.3(7)
_cell_measurement_theta_max      74.1920
_cell_measurement_theta_min      3.6840
_shelx_estimated_absorpt_T_max   0.761
_shelx_estimated_absorpt_T_min   0.679
_exptl_absorpt_coefficient_mu    1.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
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    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1439
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            102904
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.070
_diffrn_reflns_theta_max         67.070
_diffrn_reflns_theta_min         3.683
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.3(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -86.00 -61.00   1.00    1.00    --    0.00 -38.00  90.00   25
  2  ω    -16.00  21.00   1.00    1.00    --    0.00  57.00 -30.00   37
  3  ω    -30.00   3.00   1.00    1.00    --    0.00  77.00-180.00   33
  4  ω    -69.00 -22.00   1.00    1.00    --    0.00 -77.00 120.00   47
  5  ω     46.00  84.00   1.00    1.00    --    0.00  57.00 -30.00   38
  6  ω    -87.00 -25.00   1.00    1.00    --    0.00 -77.00  90.00   62
  7  ω     43.00  69.00   1.00    1.00    --    0.00  77.00  90.00   26
  8  ω     35.00  61.00   1.00    1.00    --    0.00  77.00-180.00   26
  9  ω    -88.00  15.00   1.00    1.00    --    0.00 -38.00   0.00  103
 10  ω    -51.00 -23.00   1.00    1.00    --    0.00 -38.00  90.00   28
 11  ω    -14.00  19.00   1.00    1.00    --    0.00 -38.00  90.00   33
 12  ω    -29.00  36.00   1.00    1.00    --    0.00  77.00  90.00   65
 13  ω     -5.00  30.00   1.00    1.00    --    0.00 -77.00  90.00   35
 14  ω    -80.00  19.00   1.00    1.00    --    0.00 -38.00 -60.00   99
 15  ω      5.00  30.00   1.00    1.00    --    0.00 -77.00 120.00   25
 16  ω    -87.00  17.00   1.00    1.00    --    0.00 -38.00-120.00  104
 17  ω     63.00 107.00   1.00    1.00    --   95.80  82.00-140.19   44
 18  ω     70.00 111.00   1.00    1.00    --   95.80  63.00 161.63   41
 19  ω     70.00 103.00   1.00    1.00    --   95.80  63.00 150.80   33
 20  ω    116.00 142.00   1.00    1.00    --   95.80  80.00 -21.36   26
 21  ω     65.00  93.00   1.00    1.00    --   95.80  78.00 -45.45   28
 22  ω     64.00  90.00   1.00    1.00    --   95.80  80.00 -21.36   26
 23  ω     67.00 174.00   1.00    1.00    --   95.80  72.00  -3.72  107
 24  ω     42.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   86
 25  ω     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 26  ω     63.00  89.00   1.00    1.00    --   95.80  82.00  30.00   26
 27  ω    118.00 185.00   1.00    1.00    --   95.80  82.00  30.00   67
 28  ω     65.00  91.00   1.00    1.00    --   95.80  82.00-180.00   26
 29  ω    104.00 185.00   1.00    1.00    --   95.80  82.00-180.00   81
 30  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -90.00   25
 31  ω     63.00  89.00   1.00    1.00    --   95.80  81.00 -70.07   26
 32  ω     95.00 171.00   1.00    1.00    --   95.80  78.00 165.81   76
 33  ω     65.00  90.00   1.00    1.00    --   95.80  78.00 165.81   25
 34  ω    160.00 185.00   1.00    1.00    --   95.80  78.00 -30.66   25
 35  ω     67.00 175.00   1.00    1.00    --   95.80  72.00 108.32  108
 36  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 150.00   25
 37  ω     65.00  90.00   1.00    1.00    --   95.80  76.00  77.58   25
 38  ω     65.00  90.00   1.00    1.00    --   95.80  78.00 -30.66   25
 39  ω     64.00  90.00   1.00    1.00    --   95.80  79.00 141.91   26
 40  ω     53.00 128.00   1.00    1.00    --   95.80 -82.00-120.00   75
 41  ω     75.00 183.00   1.00    1.00    --   95.80  45.00-120.00  108
 42  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 -60.00   25
 43  ω     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 44  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 45  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-120.00   25
 46  ω     65.00  91.00   1.00    1.00    --   95.80  77.00  30.00   26
 47  ω     63.00  88.00   1.00    1.00    --   95.80  82.00 120.00   25
 48  ω    110.00 184.00   1.00    1.00    --   95.80  82.00 120.00   74
 49  ω     71.00  97.00   1.00    1.00    --   95.80  61.00-150.00   26
 50  ω     63.00  89.00   1.00    1.00    --   95.80  82.00 -30.00   26
 51  ω     72.00 104.00   1.00    1.00    --   95.80  61.00  30.00   32
 52  ω     71.00 185.00   1.00    1.00    --   95.80  61.00  90.00  114
 53  ω     65.00 111.00   1.00    1.00    --   95.80  77.00 -90.00   46
 54  ω     63.00  88.00   1.00    1.00    --   95.80  82.00-150.00   25
 55  ω     65.00  90.00   1.00    1.00    --   95.80  77.00 120.00   25
 56  ω     65.00 126.00   1.00    1.00    --   95.80  77.00-120.00   61
 57  ω     63.00 147.00   1.00    1.00    --   95.80  82.00-113.01   84
 58  ω     89.00 127.00   1.00    1.00    --   95.80 -82.00  90.00   38
 59  ω     45.00  78.00   1.00    1.00    --   95.80 -82.00  90.00   33
 60  ω    104.00 176.00   1.00    1.00    --   95.80  76.00  17.31   72
 61  ω     74.00 103.00   1.00    1.00    --   95.80  49.00 -36.63   29
 62  ω    129.00 177.00   1.00    1.00    --   95.80  77.00  60.00   48
 63  ω     65.00  90.00   1.00    1.00    --   95.80  77.00  60.00   25
 64  ω     65.00  90.00   1.00    1.00    --   95.80  76.00  17.31   25
 65  ω     75.00 121.00   1.00    1.00    --   95.80  45.00   0.00   46
 66  ω     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 67  ω    111.00 184.00   1.00    1.00    --   95.80  82.00 -90.00   73
 68  ω    144.00 170.00   1.00    1.00    --   95.80  82.00-140.19   26
 69  ω     14.00 127.00   1.00    1.00    --   95.80 -82.00-180.00  113
 70  ω     45.00 104.00   1.00    1.00    --   95.80 -82.00 -30.00   59
 71  ω     67.00  92.00   1.00    1.00    --   95.80  71.00 119.26   25
 72  ω    115.00 172.00   1.00    1.00    --   95.80  81.00 -70.07   57
 73  ω    143.00 178.00   1.00    1.00    --   95.80  58.00  75.30   35
 74  ω     71.00 105.00   1.00    1.00    --   95.80  58.00  75.30   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0861593000
_diffrn_orient_matrix_UB_12      -0.0275085000
_diffrn_orient_matrix_UB_13      -0.0433518000
_diffrn_orient_matrix_UB_21      0.0661966000
_diffrn_orient_matrix_UB_22      0.0075007000
_diffrn_orient_matrix_UB_23      -0.0595440000
_diffrn_orient_matrix_UB_31      0.0284694000
_diffrn_orient_matrix_UB_32      -0.1009647000
_diffrn_orient_matrix_UB_33      0.0073657000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7304
_reflns_number_total             7476
_reflns_odcompleteness_completeness 99.98
_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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.259
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 3153 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.004(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     446
_refine_ls_number_reflns         7476
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.039
_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)+(0.0424P)²+0.7029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0827
_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:
 C7(H7), C41(H41), C37(H37), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C8(H8A,H8B), C9(H9A,H9B), C18(H18A,H18B), C14(H14A,H14B),
 C17(H17A,H17B), C11(H11A,H11B), C16(H16A,H16B), C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C3(H3), C5(H5), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C27(H27A,H27B,
 H27C), C35(H35A,H35B,H35C), C40(H40A,H40B,H40C), C36(H36A,H36B,H36C), C34(H34A,
 H34B,H34C), C38(H38A,H38B,H38C), C30(H30A,H30B,H30C), C39(H39A,H39B,H39C),
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.62737(4) 0.62789(4) 0.79090(2) 0.01092(12) Uani 1 1 d . . . . .
S1 S 0.28368(3) 0.63689(4) 0.74913(2) 0.01431(12) Uani 1 1 d . . . . .
O3 O 0.73583(10) 0.79659(11) 0.83500(7) 0.0150(3) Uani 1 1 d . . . . .
O2 O 0.57719(11) 0.64808(12) 0.44858(7) 0.0209(4) Uani 1 1 d . . . . .
O1 O 0.21339(11) 0.59186(12) 0.70457(8) 0.0223(4) Uani 1 1 d . . . . .
N1 N 0.34634(12) 0.71675(12) 0.71067(8) 0.0116(4) Uani 1 1 d . . . . .
C42 C 0.29754(16) 0.76913(17) 0.66050(10) 0.0181(5) Uani 1 1 d . . . . .
H42A H 0.241539 0.736176 0.645500 0.027 Uiso 1 1 calc GR . . . .
H42B H 0.341746 0.778905 0.625395 0.027 Uiso 1 1 calc GR . . . .
H42C H 0.277218 0.826777 0.677608 0.027 Uiso 1 1 calc GR . . . .
C19 C 0.51209(14) 0.77199(15) 0.74218(9) 0.0104(4) Uani 1 1 d . . . . .
C21 C 0.65622(15) 0.82120(16) 0.79896(10) 0.0122(4) Uani 1 1 d . . . . .
C2 C 0.57516(16) 0.74094(17) 0.54366(10) 0.0170(5) Uani 1 1 d . . . . .
C24 C 0.48657(15) 0.86284(16) 0.73394(9) 0.0138(4) Uani 1 1 d . . . . .
H24 H 0.427877 0.877343 0.714026 0.017 Uiso 1 1 calc R . . . .
C20 C 0.59782(15) 0.74874(15) 0.77650(9) 0.0109(4) Uani 1 1 d . . . . .
C7 C 0.64518(15) 0.62047(16) 0.87997(9) 0.0136(4) Uani 1 1 d . . . . .
H7 H 0.712463 0.637472 0.890341 0.016 Uiso 1 1 calc R . . . .
C3 C 0.54147(15) 0.75247(16) 0.60647(10) 0.0156(5) Uani 1 1 d . . . . .
H3 H 0.553216 0.807394 0.627294 0.019 Uiso 1 1 calc R . . . .
C1 C 0.55377(16) 0.65708(17) 0.51383(10) 0.0164(5) Uani 1 1 d . . . . .
C41 C 0.45328(14) 0.69889(15) 0.70777(9) 0.0099(4) Uani 1 1 d . . . . .
H41 H 0.464651 0.641852 0.731009 0.012 Uiso 1 1 calc R . . . .
C12 C 0.62774(18) 0.52149(16) 0.90077(10) 0.0188(5) Uani 1 1 d . . . . .
H12A H 0.562522 0.503266 0.888131 0.023 Uiso 1 1 calc R . . . .
H12B H 0.673732 0.482233 0.878718 0.023 Uiso 1 1 calc R . . . .
C5 C 0.47961(16) 0.60087(16) 0.60975(10) 0.0141(4) Uani 1 1 d . . . . .
H5 H 0.448748 0.554443 0.632318 0.017 Uiso 1 1 calc R . . . .
C4 C 0.49078(15) 0.68429(16) 0.63899(10) 0.0126(4) Uani 1 1 d . . . . .
C37 C 0.81626(17) 0.85991(18) 0.84122(12) 0.0230(5) Uani 1 1 d . . . . .
H37 H 0.792253 0.918361 0.857488 0.028 Uiso 1 1 calc R . . . .
C8 C 0.57494(16) 0.68314(17) 0.91710(10) 0.0170(5) Uani 1 1 d . . . . .
H8A H 0.587336 0.745989 0.905396 0.020 Uiso 1 1 calc R . . . .
H8B H 0.508230 0.668734 0.905414 0.020 Uiso 1 1 calc R . . . .
C25 C 0.50718(17) 0.48318(17) 0.52427(10) 0.0183(5) Uani 1 1 d . . . . .
C23 C 0.54698(15) 0.93168(16) 0.75483(11) 0.0163(4) Uani 1 1 d . . . . .
H23 H 0.529905 0.992048 0.747484 0.020 Uiso 1 1 calc R . . . .
C13 C 0.75374(15) 0.61968(16) 0.75879(10) 0.0144(4) Uani 1 1 d . . . . .
H13 H 0.790545 0.672805 0.773713 0.017 Uiso 1 1 calc R . . . .
C22 C 0.63329(15) 0.91144(16) 0.78682(10) 0.0148(4) Uani 1 1 d . . . . .
H22 H 0.675035 0.957765 0.799886 0.018 Uiso 1 1 calc R . . . .
C26 C 0.56219(19) 0.42421(18) 0.57395(11) 0.0232(5) Uani 1 1 d . . . . .
H26A H 0.628372 0.444941 0.577382 0.035 Uiso 1 1 calc GR . . . .
H26B H 0.561577 0.361803 0.560296 0.035 Uiso 1 1 calc GR . . . .
H26C H 0.530800 0.429253 0.615048 0.035 Uiso 1 1 calc GR . . . .
C6 C 0.51315(16) 0.58312(16) 0.54694(10) 0.0151(5) Uani 1 1 d . . . . .
C33 C 0.64180(18) 0.81346(18) 0.51343(11) 0.0226(5) Uani 1 1 d . . . . .
C28 C 0.55454(19) 0.46105(19) 0.45898(11) 0.0253(6) Uani 1 1 d . . . . .
H28A H 0.620012 0.484141 0.458273 0.038 Uiso 1 1 calc GR . . . .
H28B H 0.517468 0.488913 0.425140 0.038 Uiso 1 1 calc GR . . . .
H28C H 0.555645 0.396303 0.452836 0.038 Uiso 1 1 calc GR . . . .
C27 C 0.40012(18) 0.45267(19) 0.52185(12) 0.0248(6) Uani 1 1 d . . . . .
H27A H 0.396875 0.390012 0.508951 0.037 Uiso 1 1 calc GR . . . .
H27B H 0.365245 0.489498 0.491437 0.037 Uiso 1 1 calc GR . . . .
H27C H 0.371311 0.459443 0.563634 0.037 Uiso 1 1 calc GR . . . .
C35 C 0.74211(17) 0.7694(2) 0.50205(12) 0.0267(6) Uani 1 1 d . . . . .
H35A H 0.769473 0.750940 0.542480 0.040 Uiso 1 1 calc GR . . . .
H35B H 0.784709 0.812545 0.481777 0.040 Uiso 1 1 calc GR . . . .
H35C H 0.734729 0.717101 0.474781 0.040 Uiso 1 1 calc GR . . . .
C9 C 0.58803(19) 0.67149(19) 0.98970(11) 0.0243(6) Uani 1 1 d . . . . .
H9A H 0.653341 0.690279 1.001720 0.029 Uiso 1 1 calc R . . . .
H9B H 0.542071 0.710431 1.012054 0.029 Uiso 1 1 calc R . . . .
C18 C 0.80630(17) 0.53417(18) 0.78162(11) 0.0223(5) Uani 1 1 d . . . . .
H18A H 0.770041 0.480811 0.768107 0.027 Uiso 1 1 calc R . . . .
H18B H 0.809344 0.534027 0.828208 0.027 Uiso 1 1 calc R . . . .
C29 C 0.20578(17) 0.70307(19) 0.80467(12) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.75107(18) 0.6216(2) 0.68507(11) 0.0291(6) Uani 1 1 d . . . . .
H14A H 0.712403 0.570917 0.669489 0.035 Uiso 1 1 calc R . . . .
H14B H 0.720309 0.677491 0.670753 0.035 Uiso 1 1 calc R . . . .
C17 C 0.90944(18) 0.5299(2) 0.75420(13) 0.0299(6) Uani 1 1 d . . . . .
H17A H 0.947066 0.580915 0.770329 0.036 Uiso 1 1 calc R . . . .
H17B H 0.940845 0.474285 0.768455 0.036 Uiso 1 1 calc R . . . .
C11 C 0.6392(2) 0.50891(19) 0.97337(11) 0.0256(6) Uani 1 1 d . . . . .
H11A H 0.623928 0.446473 0.984707 0.031 Uiso 1 1 calc R . . . .
H11B H 0.706283 0.520658 0.985495 0.031 Uiso 1 1 calc R . . . .
C16 C 0.9082(2) 0.5325(2) 0.68100(12) 0.0297(6) Uani 1 1 d . . . . .
H16A H 0.974677 0.533577 0.665001 0.036 Uiso 1 1 calc R . . . .
H16B H 0.876869 0.478048 0.664696 0.036 Uiso 1 1 calc R . . . .
C40 C 0.4922(2) 0.6601(2) 0.40865(11) 0.0306(6) Uani 1 1 d . . . . .
H40A H 0.510692 0.655833 0.364241 0.046 Uiso 1 1 calc GR . . . .
H40B H 0.464113 0.718796 0.416762 0.046 Uiso 1 1 calc GR . . . .
H40C H 0.445313 0.613578 0.418377 0.046 Uiso 1 1 calc GR . . . .
C36 C 0.6574(2) 0.8948(2) 0.55868(13) 0.0341(7) Uani 1 1 d . . . . .
H36A H 0.596039 0.924067 0.566721 0.051 Uiso 1 1 calc GR . . . .
H36B H 0.701420 0.937305 0.539057 0.051 Uiso 1 1 calc GR . . . .
H36C H 0.684524 0.873749 0.598553 0.051 Uiso 1 1 calc GR . . . .
C34 C 0.6021(2) 0.8526(2) 0.45002(12) 0.0292(6) Uani 1 1 d . . . . .
H34A H 0.601262 0.805744 0.417863 0.044 Uiso 1 1 calc GR . . . .
H34B H 0.643137 0.901646 0.435996 0.044 Uiso 1 1 calc GR . . . .
H34C H 0.537014 0.874839 0.456637 0.044 Uiso 1 1 calc GR . . . .
C10 C 0.5720(2) 0.57310(19) 1.01027(11) 0.0264(6) Uani 1 1 d . . . . .
H10A H 0.504622 0.556238 1.002463 0.032 Uiso 1 1 calc R . . . .
H10B H 0.584437 0.567327 1.055990 0.032 Uiso 1 1 calc R . . . .
C15 C 0.8543(2) 0.6156(2) 0.65693(12) 0.0339(7) Uani 1 1 d . . . . .
H15A H 0.850222 0.613276 0.610408 0.041 Uiso 1 1 calc R . . . .
H15B H 0.890497 0.669855 0.668591 0.041 Uiso 1 1 calc R . . . .
C38 C 0.86623(18) 0.8739(2) 0.77687(13) 0.0322(6) Uani 1 1 d . . . . .
H38A H 0.892350 0.816984 0.762089 0.048 Uiso 1 1 calc GR . . . .
H38B H 0.918158 0.917170 0.781644 0.048 Uiso 1 1 calc GR . . . .
H38C H 0.819798 0.896301 0.746186 0.048 Uiso 1 1 calc GR . . . .
C30 C 0.2716(2) 0.7671(2) 0.84258(14) 0.0420(8) Uani 1 1 d . . . . .
H30A H 0.324953 0.733364 0.860527 0.063 Uiso 1 1 calc GR . . . .
H30B H 0.234833 0.794933 0.876600 0.063 Uiso 1 1 calc GR . . . .
H30C H 0.296407 0.813509 0.814478 0.063 Uiso 1 1 calc GR . . . .
C39 C 0.8821(2) 0.8163(2) 0.89058(15) 0.0401(7) Uani 1 1 d . . . . .
H39A H 0.847173 0.808978 0.930230 0.060 Uiso 1 1 calc GR . . . .
H39B H 0.937993 0.854389 0.897586 0.060 Uiso 1 1 calc GR . . . .
H39C H 0.903037 0.757829 0.875298 0.060 Uiso 1 1 calc GR . . . .
C32 C 0.1623(2) 0.6295(2) 0.84839(13) 0.0375(7) Uani 1 1 d . . . . .
H32A H 0.122272 0.589381 0.823318 0.056 Uiso 1 1 calc GR . . . .
H32B H 0.123438 0.657723 0.881183 0.056 Uiso 1 1 calc GR . . . .
H32C H 0.214062 0.595413 0.868031 0.056 Uiso 1 1 calc GR . . . .
C31 C 0.1248(2) 0.7535(2) 0.76942(14) 0.0357(7) Uani 1 1 d . . . . .
H31A H 0.151636 0.805352 0.747631 0.053 Uiso 1 1 calc GR . . . .
H31B H 0.076577 0.773410 0.799800 0.053 Uiso 1 1 calc GR . . . .
H31C H 0.095039 0.713532 0.738626 0.053 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
P1 C20 1.846(2) . ?
P1 C7 1.872(2) . ?
P1 C13 1.861(2) . ?
S1 O1 1.4922(16) . ?
S1 N1 1.6599(18) . ?
S1 C29 1.850(2) . ?
O3 C21 1.373(2) . ?
O3 C37 1.449(3) . ?
O2 C1 1.401(2) . ?
O2 C40 1.442(3) . ?
N1 C42 1.459(3) . ?
N1 C41 1.491(2) . ?
C19 C24 1.391(3) . ?
C19 C20 1.417(3) . ?
C19 C41 1.522(3) . ?
C21 C20 1.412(3) . ?
C21 C22 1.386(3) . ?
C2 C3 1.396(3) . ?
C2 C1 1.410(3) . ?
C2 C33 1.538(3) . ?
C24 C23 1.378(3) . ?
C7 C12 1.536(3) . ?
C7 C8 1.540(3) . ?
C3 C4 1.394(3) . ?
C1 C6 1.402(3) . ?
C41 C4 1.535(3) . ?
C12 C11 1.530(3) . ?
C5 C4 1.377(3) . ?
C5 C6 1.410(3) . ?
C37 C38 1.518(4) . ?
C37 C39 1.510(3) . ?
C8 C9 1.530(3) . ?
C25 C26 1.545(3) . ?
C25 C6 1.544(3) . ?
C25 C28 1.540(3) . ?
C25 C27 1.536(3) . ?
C23 C22 1.390(3) . ?
C13 C18 1.524(3) . ?
C13 C14 1.534(3) . ?
C33 C35 1.539(3) . ?
C33 C36 1.536(4) . ?
C33 C34 1.539(3) . ?
C9 C10 1.524(4) . ?
C18 C17 1.526(3) . ?
C29 C30 1.524(4) . ?
C29 C32 1.533(4) . ?
C29 C31 1.523(4) . ?
C14 C15 1.534(3) . ?
C17 C16 1.523(4) . ?
C11 C10 1.526(3) . ?
C16 C15 1.513(4) . ?

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
C20 P1 C7 104.20(10) . . ?
C20 P1 C13 102.04(10) . . ?
C13 P1 C7 103.29(9) . . ?
O1 S1 N1 110.39(9) . . ?
O1 S1 C29 104.36(11) . . ?
N1 S1 C29 103.20(11) . . ?
C21 O3 C37 119.01(17) . . ?
C1 O2 C40 111.18(17) . . ?
C42 N1 S1 118.70(14) . . ?
C42 N1 C41 120.99(17) . . ?
C41 N1 S1 113.85(14) . . ?
C24 C19 C20 120.15(19) . . ?
C24 C19 C41 119.08(18) . . ?
C20 C19 C41 120.43(19) . . ?
O3 C21 C20 115.67(19) . . ?
O3 C21 C22 122.14(19) . . ?
C22 C21 C20 122.17(19) . . ?
C3 C2 C1 116.7(2) . . ?
C3 C2 C33 119.7(2) . . ?
C1 C2 C33 123.3(2) . . ?
C23 C24 C19 120.96(19) . . ?
C19 C20 P1 119.72(16) . . ?
C21 C20 P1 123.17(16) . . ?
C21 C20 C19 117.1(2) . . ?
C12 C7 P1 108.28(15) . . ?
C12 C7 C8 109.11(17) . . ?
C8 C7 P1 112.33(15) . . ?
C4 C3 C2 122.1(2) . . ?
O2 C1 C2 117.4(2) . . ?
O2 C1 C6 119.6(2) . . ?
C6 C1 C2 122.94(19) . . ?
N1 C41 C19 112.21(16) . . ?
N1 C41 C4 113.07(16) . . ?
C19 C41 C4 111.06(16) . . ?
C11 C12 C7 112.1(2) . . ?
C4 C5 C6 122.5(2) . . ?
C3 C4 C41 121.2(2) . . ?
C5 C4 C3 118.73(19) . . ?
C5 C4 C41 119.92(19) . . ?
O3 C37 C38 110.6(2) . . ?
O3 C37 C39 104.1(2) . . ?
C39 C37 C38 112.8(2) . . ?
C9 C8 C7 110.77(19) . . ?
C6 C25 C26 107.64(18) . . ?
C28 C25 C26 105.40(19) . . ?
C28 C25 C6 116.6(2) . . ?
C27 C25 C26 109.0(2) . . ?
C27 C25 C6 109.77(19) . . ?
C27 C25 C28 108.21(19) . . ?
C24 C23 C22 120.4(2) . . ?
C18 C13 P1 112.45(15) . . ?
C18 C13 C14 109.75(19) . . ?
C14 C13 P1 109.59(15) . . ?
C21 C22 C23 119.0(2) . . ?
C1 C6 C5 116.2(2) . . ?
C1 C6 C25 127.45(19) . . ?
C5 C6 C25 116.2(2) . . ?
C2 C33 C35 107.6(2) . . ?
C2 C33 C34 113.5(2) . . ?
C36 C33 C2 111.78(19) . . ?
C36 C33 C35 107.3(2) . . ?
C36 C33 C34 106.5(2) . . ?
C34 C33 C35 110.00(19) . . ?
C10 C9 C8 111.5(2) . . ?
C13 C18 C17 110.8(2) . . ?
C30 C29 S1 107.81(17) . . ?
C30 C29 C32 111.0(2) . . ?
C32 C29 S1 102.97(19) . . ?
C31 C29 S1 112.10(17) . . ?
C31 C29 C30 112.4(3) . . ?
C31 C29 C32 110.2(2) . . ?
C15 C14 C13 111.0(2) . . ?
C16 C17 C18 111.3(2) . . ?
C10 C11 C12 111.1(2) . . ?
C15 C16 C17 110.9(2) . . ?
C9 C10 C11 111.0(2) . . ?
C16 C15 C14 111.8(2) . . ?

_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 2.661
_oxdiff_exptl_absorpt_empirical_full_min 0.391
