# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ritonavir
_database_code_depnum_ccdc_archive 'CCDC 2009282'
loop_
_audit_author_name
_audit_author_address
'Christopher Pask'
;University of Leeds
United Kingdom
;
_audit_update_record             
;
2020-06-11 deposited with the CCDC.	2023-02-14 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C37 H49 N6 O5 S2, C2 H O4, 0.5(C2 H2 O4), 0.5(C3 H6 O)'
_chemical_formula_sum            'C41.50 H54 N6 O11.50 S2'
_chemical_formula_weight         885.02
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C83  H108  N12  O23  S4  '
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.2615(2)
_cell_length_b                   25.2098(9)
_cell_length_c                   16.6111(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.994(3)
_cell_angle_gamma                90
_cell_volume                     2201.99(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6386
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      72.9630
_cell_measurement_theta_min      4.3820
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.645
_exptl_absorpt_coefficient_mu    1.657
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             938
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -15 4 0.0135
0 15 -4 0.0135
0 -16 -1 0.0146
0 16 1 0.0146
2 13 -2 0.0779
-2 -13 2 0.0779
1 5 10 0.0123
-1 9 -9 0.0296

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0028 -14.9714 3.9862 0.3957 0.0027 0.9048
0.0028 14.9714 -3.9862 -0.3957 -0.0027 -0.9048
-0.0026 -15.9724 -1.0054 0.6006 -0.3573 0.6884
0.0026 15.9724 1.0054 -0.6006 0.3573 -0.6884
2.0028 12.9722 -1.9870 0.0254 0.4683 -0.8831
-2.0028 -12.9722 1.9870 -0.0254 -0.4683 0.8831
1.0005 4.9948 9.9865 -0.3070 0.9594 0.2058
-0.9982 8.9811 -8.9820 -0.2228 -0.6382 -0.8015

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17561
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.738
_diffrn_reflns_theta_min         3.506
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -91.00 -21.00   1.00   15.00    --  -41.04 -37.00 -60.00   70
  2  ω    -54.00  30.00   1.00   15.00    --  -41.04  37.00  60.00   84
  3  ω   -109.00 -71.00   1.00   15.00    --  -41.04 -37.00 120.00   38
  4  ω   -112.00 -19.00   1.00   15.00    --  -41.04 -37.00-120.00   93
  5  ω      1.00  64.00   1.00   15.00    --   41.04 -57.00 120.00   63
  6  ω    -26.00   0.00   1.00   15.00    --   41.04 -57.00 120.00   26
  7  ω     80.00 173.00   1.00   60.00    --  106.02  45.00  90.00   93
  8  ω    136.00 177.00   1.00   60.00    --  106.02  30.00 -90.00   41
  9  ω     68.00 134.00   1.00   60.00    --  106.02 -61.00  30.00   66
 10  ω     82.00 172.00   1.00   60.00    --  106.02  30.00-180.00   90
 11  ω     78.00 112.00   1.00   60.00    --  106.02  61.00 -60.00   34
 12  ω     80.00 115.00   1.00   60.00    --  106.02  45.00   0.00   35
 13  ω    150.00 177.00   1.00   60.00    --  106.02  61.00 -90.00   27
 14  ω     40.00 122.00   1.00   60.00    --  106.02 -45.00-120.00   82
 15  ω     90.00 134.00   1.00   60.00    --  106.02 -30.00 -90.00   44
 16  ω     78.00 116.00   1.00   60.00    --  106.02  61.00 -90.00   38
 17  ω     81.00 176.00   1.00   60.00    --  106.02  45.00  30.00   95
 18  ω     77.00 103.00   1.00   60.00    --  106.02  61.00   0.00   26
 19  ω     40.00  65.00   1.00   60.00    --  106.02 -30.00 -90.00   25
 20  ω     65.00 131.00   1.00   60.00    --  106.02 -45.00  90.00   66
 21  ω     78.00 103.00   1.00   60.00    --  106.02  61.00 -30.00   25
 22  ω     82.00 166.00   1.00   60.00    --  106.02  45.00 -30.00   84
 23  ω     78.00 105.00   1.00   60.00    --  106.02  61.00 -33.86   27
 24  ω     78.00 103.00   1.00   60.00    --  106.02  61.00 -40.01   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2089756000
_diffrn_orient_matrix_UB_12      -0.0355017000
_diffrn_orient_matrix_UB_13      -0.0339216000
_diffrn_orient_matrix_UB_21      0.1850753000
_diffrn_orient_matrix_UB_22      0.0180246000
_diffrn_orient_matrix_UB_23      0.0685132000
_diffrn_orient_matrix_UB_31      -0.0882006000
_diffrn_orient_matrix_UB_32      -0.0463985000
_diffrn_orient_matrix_UB_33      0.0526473000
_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         0.920
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.950
_reflns_number_gt                7439
_reflns_number_total             8613
_reflns_odcompleteness_completeness 99.93
_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 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_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         0.441
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details 
;
 Flack x determined using 2982 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         8613
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.031
_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)+(0.0665P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          
;
The positions of heteroatom bound hydrogen atoms in the main ritonavir moiety
and the fully occupied oxalate anion were located in the Fourier Map, but
placed in calculated positions and refined isotropically.

Residual electron density was modelled as half a molecule of oxalic acid and
half a molecule of acetone and refined isotropically. C-C, C-O and C=O
distances in oxalic acid were restrained to 1.52(2), 1.30(2) and 1.22(2) Ã?
respectively. 
C-C and C=O distances in acetone were restrained to 1.52(2) and 1.22(2) Ã?
respectively. 
Thermal ellipsoids of one phenyl ring in ritonavir were restrained using a
rigid bond restraint.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O11-C40 = O13-C41
 1.3 with sigma of 0.02
 O10-C40 = O12-C41
 1.22 with sigma of 0.02
 C41-C40
 1.51 with sigma of 0.02
 O14-C42
 1.22 with sigma of 0.02
 C43-C42 = C44-C42
 1.52 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C8, C9, C10, C11, C12, C13
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Fixed Sof: O10(0.5) O11(0.5) H11A(0.5) O12(0.5) O13(0.5) H13A(0.5) C40(0.5)
 C41(0.5) O14(0.5) C42(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C44(0.5)
 H44A(0.5) H44B(0.5) H44C(0.5)
5.a Ternary CH refined with riding coordinates:
 C6(H6A), C14(H14), C16(H16), C25(H25), C26(H26), C35(H35)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C15(H15A,H15B), C17(H17A,H17B), C31(H31A,H31B)
5.c Me refined with riding coordinates:
 C43(H43A,H43B,H43C), C44(H44A,H44B,H44C)
5.d Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N6(H6), C1(H1), C2(H2A), C9(H9), C10(H10), C11(H11), C12(H12),
  C13(H13), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C33(H33)
5.e Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C)
5.f Idealised tetrahedral OH refined as rotating group:
 O3(H3), O9(H9A), O11(H11A), O13(H13A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.9829(3) 0.37237(6) 0.37182(9) 0.0512(4) Uani 1 1 d . . . . .
S2 S 1.1945(2) 0.32282(5) 0.86280(7) 0.0385(3) Uani 1 1 d . . . . .
O1 O 0.4844(7) 0.46991(13) 0.4765(2) 0.0382(8) Uani 1 1 d . . . . .
O2 O 0.8195(6) 0.52665(14) 0.4662(2) 0.0364(7) Uani 1 1 d . . . . .
O3 O 0.1957(6) 0.65748(13) 0.53788(18) 0.0299(6) Uani 1 1 d . . . . .
H3 H 0.1252 0.6786 0.5069 0.045 Uiso 1 1 calc GR . . . .
O4 O 0.3218(5) 0.60689(12) 0.77752(18) 0.0276(6) Uani 1 1 d . . . . .
O5 O 0.6218(7) 0.46778(13) 0.7953(2) 0.0403(8) Uani 1 1 d . . . . .
N1 N 0.7550(15) 0.4162(2) 0.2523(3) 0.0687(18) Uani 1 1 d . . . . .
N2 N 0.4085(7) 0.55585(13) 0.4632(2) 0.0242(7) Uani 1 1 d . . . . .
H2 H 0.2544 0.5470 0.4723 0.029 Uiso 1 1 calc R . . . .
N3 N 0.7023(7) 0.63334(14) 0.7308(2) 0.0242(7) Uani 1 1 d . . . . .
H3A H 0.891(11) 0.624(2) 0.735(3) 0.036(14) Uiso 1 1 d . . . . .
N4 N 0.8890(7) 0.53886(14) 0.8050(2) 0.0260(7) Uani 1 1 d . . . . .
H4 H 1.0449 0.5488 0.8022 0.031 Uiso 1 1 calc R . . . .
N5 N 0.9559(9) 0.47056(15) 0.7136(2) 0.0349(9) Uani 1 1 d . . . . .
N6 N 0.8537(7) 0.32839(15) 0.7558(2) 0.0274(7) Uani 1 1 d . . . . .
H6 H 0.7278 0.3202 0.7238 0.033 Uiso 1 1 calc R . . . .
C1 C 0.9367(15) 0.3839(3) 0.2706(4) 0.0581(16) Uani 1 1 d . . . . .
H1 H 1.0354 0.3680 0.2320 0.070 Uiso 1 1 calc R . . . .
C2 C 0.6419(15) 0.4342(2) 0.3206(4) 0.0598(18) Uani 1 1 d . . . . .
H2A H 0.5069 0.4580 0.3183 0.072 Uiso 1 1 calc R . . . .
C3 C 0.7387(11) 0.41515(19) 0.3908(3) 0.0378(11) Uani 1 1 d . . . . .
C4 C 0.6611(12) 0.4264(2) 0.4747(3) 0.0446(13) Uani 1 1 d . . . . .
H4A H 0.5831 0.3950 0.4968 0.054 Uiso 1 1 calc R . . . .
H4B H 0.8106 0.4349 0.5080 0.054 Uiso 1 1 calc R . . . .
C5 C 0.5908(9) 0.51910(17) 0.4678(2) 0.0266(9) Uani 1 1 d . . . . .
C6 C 0.4656(8) 0.61093(16) 0.4429(2) 0.0248(8) Uani 1 1 d . . . . .
H6A H 0.6397 0.6120 0.4239 0.030 Uiso 1 1 calc R . . . .
C7 C 0.2872(10) 0.62860(19) 0.3729(3) 0.0332(10) Uani 1 1 d . . . . .
H7A H 0.1130 0.6265 0.3900 0.040 Uiso 1 1 calc R . . . .
H7B H 0.3224 0.6654 0.3606 0.040 Uiso 1 1 calc R . . . .
C8 C 0.3112(9) 0.59634(18) 0.2980(3) 0.0319(10) Uani 1 1 d . U . . .
C9 C 0.1422(13) 0.5563(2) 0.2767(4) 0.0488(13) Uani 1 1 d . U . . .
H9 H 0.0106 0.5479 0.3104 0.059 Uiso 1 1 calc R . . . .
C10 C 0.1682(19) 0.5285(3) 0.2051(5) 0.074(2) Uani 1 1 d . U . . .
H10 H 0.0557 0.5013 0.1913 0.089 Uiso 1 1 calc R . . . .
C11 C 0.3632(18) 0.5417(4) 0.1542(4) 0.079(2) Uani 1 1 d . U . . .
H11 H 0.3809 0.5236 0.1060 0.094 Uiso 1 1 calc R . . . .
C12 C 0.5262(17) 0.5809(4) 0.1755(4) 0.084(2) Uani 1 1 d . U . . .
H12 H 0.6550 0.5901 0.1412 0.100 Uiso 1 1 calc R . . . .
C13 C 0.5050(13) 0.6074(4) 0.2467(3) 0.0619(17) Uani 1 1 d . U . . .
H13 H 0.6236 0.6334 0.2609 0.074 Uiso 1 1 calc R . . . .
C14 C 0.4521(8) 0.64915(17) 0.5143(2) 0.0243(8) Uani 1 1 d . . . . .
H14 H 0.5255 0.6833 0.4992 0.029 Uiso 1 1 calc R . . . .
C15 C 0.5993(8) 0.62770(16) 0.5877(2) 0.0236(8) Uani 1 1 d . . . . .
H15A H 0.7738 0.6215 0.5731 0.028 Uiso 1 1 calc R . . . .
H15B H 0.5272 0.5937 0.6020 0.028 Uiso 1 1 calc R . . . .
C16 C 0.6006(8) 0.66359(16) 0.6618(2) 0.0240(8) Uani 1 1 d . . . . .
H16 H 0.4246 0.6734 0.6723 0.029 Uiso 1 1 calc R . . . .
C17 C 0.7571(9) 0.71488(16) 0.6536(3) 0.0273(9) Uani 1 1 d . . . . .
H17A H 0.9287 0.7059 0.6389 0.033 Uiso 1 1 calc R . . . .
H17B H 0.6816 0.7366 0.6110 0.033 Uiso 1 1 calc R . . . .
C18 C 0.7667(9) 0.74601(16) 0.7316(3) 0.0284(9) Uani 1 1 d . . . . .
C19 C 0.5712(11) 0.7801(2) 0.7510(4) 0.0436(12) Uani 1 1 d . . . . .
H19 H 0.4395 0.7869 0.7136 0.052 Uiso 1 1 calc R . . . .
C20 C 0.5723(14) 0.8041(3) 0.8270(4) 0.0599(17) Uani 1 1 d . . . . .
H20 H 0.4387 0.8264 0.8399 0.072 Uiso 1 1 calc R . . . .
C21 C 0.7667(13) 0.7955(2) 0.8826(3) 0.0531(16) Uani 1 1 d . . . . .
H21 H 0.7654 0.8119 0.9328 0.064 Uiso 1 1 calc R . . . .
C22 C 0.9627(13) 0.7626(2) 0.8635(3) 0.0464(13) Uani 1 1 d . . . . .
H22 H 1.0954 0.7566 0.9009 0.056 Uiso 1 1 calc R . . . .
C23 C 0.9643(10) 0.73786(19) 0.7881(3) 0.0344(10) Uani 1 1 d . . . . .
H23 H 1.0988 0.7158 0.7756 0.041 Uiso 1 1 calc R . . . .
C24 C 0.5580(8) 0.60592(16) 0.7808(2) 0.0223(8) Uani 1 1 d . . . . .
C25 C 0.7062(8) 0.57303(16) 0.8446(2) 0.0249(8) Uani 1 1 d . . . . .
H25 H 0.5845 0.5501 0.8714 0.030 Uiso 1 1 calc R . . . .
C26 C 0.8368(9) 0.60813(17) 0.9089(2) 0.0276(9) Uani 1 1 d . . . . .
H26 H 0.9674 0.6293 0.8832 0.033 Uiso 1 1 calc R . . . .
C27 C 0.6439(10) 0.6458(2) 0.9445(3) 0.0397(11) Uani 1 1 d . . . . .
H27A H 0.5093 0.6257 0.9673 0.060 Uiso 1 1 calc GR . . . .
H27B H 0.5748 0.6686 0.9028 0.060 Uiso 1 1 calc GR . . . .
H27C H 0.7263 0.6670 0.9857 0.060 Uiso 1 1 calc GR . . . .
C28 C 0.9660(11) 0.5744(2) 0.9750(3) 0.0399(11) Uani 1 1 d . . . . .
H28A H 0.8409 0.5530 1.0004 0.060 Uiso 1 1 calc GR . . . .
H28B H 1.0471 0.5972 1.0144 0.060 Uiso 1 1 calc GR . . . .
H28C H 1.0910 0.5519 0.9518 0.060 Uiso 1 1 calc GR . . . .
C29 C 0.8144(9) 0.49159(17) 0.7727(3) 0.0284(9) Uani 1 1 d . . . . .
C30 C 1.1398(10) 0.5005(2) 0.6683(3) 0.0375(11) Uani 1 1 d . . . . .
H30A H 1.1020 0.5377 0.6717 0.056 Uiso 1 1 calc GR . . . .
H30B H 1.1307 0.4895 0.6129 0.056 Uiso 1 1 calc GR . . . .
H30C H 1.3079 0.4940 0.6905 0.056 Uiso 1 1 calc GR . . . .
C31 C 0.8959(12) 0.41645(18) 0.6892(3) 0.0410(12) Uani 1 1 d . . . . .
H31A H 0.9789 0.4087 0.6393 0.049 Uiso 1 1 calc R . . . .
H31B H 0.7138 0.4134 0.6790 0.049 Uiso 1 1 calc R . . . .
C32 C 0.9776(9) 0.37623(17) 0.7513(3) 0.0294(9) Uani 1 1 d . . . . .
C33 C 1.1728(9) 0.37929(19) 0.8063(3) 0.0331(10) Uani 1 1 d . . . . .
H33 H 1.2809 0.4083 0.8124 0.040 Uiso 1 1 calc R . . . .
C34 C 0.9408(9) 0.29594(19) 0.8123(3) 0.0307(9) Uani 1 1 d . . . . .
C35 C 0.8388(10) 0.2418(2) 0.8271(3) 0.0409(12) Uani 1 1 d . . . . .
H35 H 0.6811 0.2374 0.7945 0.049 Uiso 1 1 calc R . . . .
C36 C 1.0300(14) 0.2003(2) 0.8001(4) 0.0527(15) Uani 1 1 d . . . . .
H36A H 1.0621 0.2053 0.7440 0.079 Uiso 1 1 calc GR . . . .
H36B H 0.9619 0.1654 0.8080 0.079 Uiso 1 1 calc GR . . . .
H36C H 1.1861 0.2041 0.8312 0.079 Uiso 1 1 calc GR . . . .
C37 C 0.7788(12) 0.2336(2) 0.9150(3) 0.0491(13) Uani 1 1 d . . . . .
H37A H 0.9341 0.2333 0.9470 0.074 Uiso 1 1 calc GR . . . .
H37B H 0.6923 0.2003 0.9210 0.074 Uiso 1 1 calc GR . . . .
H37C H 0.6719 0.2619 0.9324 0.074 Uiso 1 1 calc GR . . . .
O6 O 1.5204(7) 0.29725(17) 0.5360(2) 0.0436(9) Uani 1 1 d . . . . .
O7 O 1.4470(7) 0.29702(17) 0.6684(2) 0.0459(9) Uani 1 1 d . . . . .
O8 O 1.0485(7) 0.23084(14) 0.5699(2) 0.0444(9) Uani 1 1 d . . . . .
O9 O 0.9665(6) 0.31872(14) 0.5659(2) 0.0370(7) Uani 1 1 d . . . . .
H9A H 0.8239 0.3093 0.5503 0.055 Uiso 1 1 calc GR . . . .
C38 C 1.3845(8) 0.29201(17) 0.5965(3) 0.0268(9) Uani 1 1 d . . . . .
C39 C 1.1117(9) 0.27733(17) 0.5755(2) 0.0286(9) Uani 1 1 d . . . . .
O10 O 0.6353(17) 0.3739(4) 0.9318(5) 0.036(2) Uiso 0.5 1 d D . P A 2
O11 O 0.6080(15) 0.4620(3) 0.9457(5) 0.0443(17) Uiso 0.5 1 d D . P A 2
H11A H 0.5907 0.4613 0.8965 0.066 Uiso 0.5 1 calc GR . P A 2
O12 O 0.937(2) 0.4063(5) 1.0829(8) 0.083(3) Uiso 0.5 1 d D . P A 2
O13 O 0.5479(16) 0.4258(3) 1.1084(5) 0.053(2) Uiso 0.5 1 d D . P A 2
H13A H 0.6088 0.4416 1.1476 0.079 Uiso 0.5 1 calc GR . P A 2
C40 C 0.637(2) 0.4148(4) 0.9725(6) 0.030(2) Uiso 0.5 1 d D . P A 2
C41 C 0.7230(18) 0.4140(4) 1.0613(6) 0.035(2) Uiso 0.5 1 d D . P A 2
O14 O 0.669(3) 0.3633(5) 0.9452(8) 0.072(4) Uiso 0.5 1 d D . P B 1
C42 C 0.699(2) 0.4041(5) 0.9815(8) 0.043(3) Uiso 0.5 1 d D . P B 1
C43 C 0.475(4) 0.4376(8) 1.0018(14) 0.099(6) Uiso 0.5 1 d D . P B 1
H43A H 0.5332 0.4685 1.0307 0.149 Uiso 0.5 1 calc R . P B 1
H43B H 0.3858 0.4481 0.9531 0.149 Uiso 0.5 1 calc R . P B 1
H43C H 0.3637 0.4175 1.0347 0.149 Uiso 0.5 1 calc R . P B 1
C44 C 0.958(3) 0.4198(7) 1.0118(11) 0.077(4) Uiso 0.5 1 d D . P B 1
H44A H 0.9485 0.4532 1.0393 0.116 Uiso 0.5 1 calc R . P B 1
H44B H 1.0237 0.3933 1.0483 0.116 Uiso 0.5 1 calc R . P B 1
H44C H 1.0683 0.4231 0.9672 0.116 Uiso 0.5 1 calc R . P B 1


_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 C1 1.715(6) . ?
S1 C3 1.715(5) . ?
S2 C33 1.707(5) . ?
S2 C34 1.693(5) . ?
O1 C4 1.439(6) . ?
O1 C5 1.370(6) . ?
O2 C5 1.219(6) . ?
O3 H3 0.8200 . ?
O3 C14 1.433(5) . ?
O4 C24 1.242(5) . ?
O5 C29 1.247(6) . ?
N1 C1 1.285(10) . ?
N1 C2 1.375(9) . ?
N2 H2 0.8600 . ?
N2 C5 1.334(6) . ?
N2 C6 1.462(5) . ?
N3 H3A 1.02(6) . ?
N3 C16 1.462(5) . ?
N3 C24 1.337(6) . ?
N4 H4 0.8600 . ?
N4 C25 1.464(6) . ?
N4 C29 1.359(5) . ?
N5 C29 1.361(7) . ?
N5 C30 1.457(7) . ?
N5 C31 1.454(6) . ?
N6 H6 0.8600 . ?
N6 C32 1.374(6) . ?
N6 C34 1.315(6) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9300 . ?
C2 C3 1.345(8) . ?
C3 C4 1.492(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C6 H6A 0.9800 . ?
C6 C7 1.535(6) . ?
C6 C14 1.532(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.496(6) . ?
C8 C9 1.382(8) . ?
C8 C13 1.380(8) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(13) . ?
C11 H11 0.9300 . ?
C11 C12 1.348(14) . ?
C12 H12 0.9300 . ?
C12 C13 1.365(10) . ?
C13 H13 0.9300 . ?
C14 H14 0.9800 . ?
C14 C15 1.520(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.527(5) . ?
C16 H16 0.9800 . ?
C16 C17 1.541(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.514(6) . ?
C18 C19 1.387(7) . ?
C18 C23 1.391(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.400(8) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(11) . ?
C21 H21 0.9300 . ?
C21 C22 1.370(10) . ?
C22 H22 0.9300 . ?
C22 C23 1.400(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.537(6) . ?
C25 H25 0.9800 . ?
C25 C26 1.532(6) . ?
C26 H26 0.9800 . ?
C26 C27 1.525(7) . ?
C26 C28 1.529(7) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 C32 1.499(6) . ?
C32 C33 1.352(7) . ?
C33 H33 0.9300 . ?
C34 C35 1.491(7) . ?
C35 H35 0.9800 . ?
C35 C36 1.529(9) . ?
C35 C37 1.519(8) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
O6 C38 1.260(6) . ?
O7 C38 1.235(6) . ?
O8 C39 1.221(6) . ?
O9 H9A 0.8200 . ?
O9 C39 1.300(6) . ?
C38 C39 1.512(6) . ?
O10 C40 1.232(12) . ?
O11 H11A 0.8200 . ?
O11 C40 1.278(13) . ?
O12 C41 1.186(14) . ?
O13 H13A 0.8200 . ?
O13 C41 1.265(12) . ?
C40 C41 1.529(13) . ?
O14 C42 1.200(15) . ?
C42 C43 1.497(19) . ?
C42 C44 1.489(18) . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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
C1 S1 C3 89.6(3) . . ?
C34 S2 C33 91.4(2) . . ?
C5 O1 C4 114.9(4) . . ?
C14 O3 H3 109.5 . . ?
C1 N1 C2 110.8(5) . . ?
C5 N2 H2 119.3 . . ?
C5 N2 C6 121.3(4) . . ?
C6 N2 H2 119.3 . . ?
C16 N3 H3A 121(3) . . ?
C24 N3 H3A 114(3) . . ?
C24 N3 C16 123.8(4) . . ?
C25 N4 H4 119.7 . . ?
C29 N4 H4 119.7 . . ?
C29 N4 C25 120.5(4) . . ?
C29 N5 C30 124.1(4) . . ?
C29 N5 C31 116.6(4) . . ?
C31 N5 C30 119.0(4) . . ?
C32 N6 H6 122.3 . . ?
C34 N6 H6 122.3 . . ?
C34 N6 C32 115.5(4) . . ?
S1 C1 H1 122.7 . . ?
N1 C1 S1 114.7(5) . . ?
N1 C1 H1 122.7 . . ?
N1 C2 H2A 122.1 . . ?
C3 C2 N1 115.8(6) . . ?
C3 C2 H2A 122.1 . . ?
C2 C3 S1 109.2(4) . . ?
C2 C3 C4 129.3(5) . . ?
C4 C3 S1 121.5(4) . . ?
O1 C4 C3 111.3(4) . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
O2 C5 O1 123.4(4) . . ?
O2 C5 N2 126.8(4) . . ?
N2 C5 O1 109.8(4) . . ?
N2 C6 H6A 107.6 . . ?
N2 C6 C7 109.0(4) . . ?
N2 C6 C14 113.8(3) . . ?
C7 C6 H6A 107.6 . . ?
C14 C6 H6A 107.6 . . ?
C14 C6 C7 111.1(3) . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.9(4) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C9 C8 C7 122.5(5) . . ?
C13 C8 C7 119.3(5) . . ?
C13 C8 C9 118.2(5) . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.3(7) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.7(7) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(6) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.0(9) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(8) . . ?
C12 C13 H13 119.3 . . ?
O3 C14 C6 111.9(3) . . ?
O3 C14 H14 108.9 . . ?
O3 C14 C15 106.9(3) . . ?
C6 C14 H14 108.9 . . ?
C15 C14 C6 111.2(3) . . ?
C15 C14 H14 108.9 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C14 C15 C16 115.0(3) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
N3 C16 C15 108.3(3) . . ?
N3 C16 H16 108.3 . . ?
N3 C16 C17 108.9(3) . . ?
C15 C16 H16 108.3 . . ?
C15 C16 C17 114.4(3) . . ?
C17 C16 H16 108.3 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.2(3) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C19 C18 C17 121.2(5) . . ?
C19 C18 C23 118.5(4) . . ?
C23 C18 C17 120.1(4) . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.9(6) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.4 . . ?
C21 C20 C19 121.2(6) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.3(5) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.3(6) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 120.7(5) . . ?
C18 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
O4 C24 N3 123.5(4) . . ?
O4 C24 C25 121.6(4) . . ?
N3 C24 C25 115.0(4) . . ?
N4 C25 C24 109.5(3) . . ?
N4 C25 H25 107.9 . . ?
N4 C25 C26 111.5(4) . . ?
C24 C25 H25 107.9 . . ?
C26 C25 C24 112.0(3) . . ?
C26 C25 H25 107.9 . . ?
C25 C26 H26 108.4 . . ?
C27 C26 C25 110.0(4) . . ?
C27 C26 H26 108.4 . . ?
C27 C26 C28 110.7(4) . . ?
C28 C26 C25 111.0(4) . . ?
C28 C26 H26 108.4 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O5 C29 N4 122.0(4) . . ?
O5 C29 N5 120.0(4) . . ?
N4 C29 N5 118.0(4) . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 H31A 109.0 . . ?
N5 C31 H31B 109.0 . . ?
N5 C31 C32 112.9(4) . . ?
H31A C31 H31B 107.8 . . ?
C32 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
N6 C32 C31 120.4(4) . . ?
C33 C32 N6 111.4(4) . . ?
C33 C32 C31 128.2(4) . . ?
S2 C33 H33 124.5 . . ?
C32 C33 S2 111.0(4) . . ?
C32 C33 H33 124.5 . . ?
N6 C34 S2 110.7(3) . . ?
N6 C34 C35 124.6(4) . . ?
C35 C34 S2 124.6(3) . . ?
C34 C35 H35 108.3 . . ?
C34 C35 C36 109.5(5) . . ?
C34 C35 C37 111.7(5) . . ?
C36 C35 H35 108.3 . . ?
C37 C35 H35 108.3 . . ?
C37 C35 C36 110.5(5) . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C35 C37 H37A 109.5 . . ?
C35 C37 H37B 109.5 . . ?
C35 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C39 O9 H9A 109.5 . . ?
O6 C38 C39 113.7(4) . . ?
O7 C38 O6 128.4(4) . . ?
O7 C38 C39 117.8(4) . . ?
O8 C39 O9 127.2(4) . . ?
O8 C39 C38 120.4(4) . . ?
O9 C39 C38 112.4(4) . . ?
C40 O11 H11A 109.5 . . ?
C41 O13 H13A 109.5 . . ?
O10 C40 O11 126.2(10) . . ?
O10 C40 C41 120.9(10) . . ?
O11 C40 C41 112.1(8) . . ?
O12 C41 O13 123.8(11) . . ?
O12 C41 C40 122.8(11) . . ?
O13 C41 C40 113.2(9) . . ?
O14 C42 C43 120.4(15) . . ?
O14 C42 C44 120.1(15) . . ?
C44 C42 C43 119.3(14) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?


_olex2_date_sample_data_collection 2018-10-22
_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 1.345
_oxdiff_exptl_absorpt_empirical_full_min 0.834
