# Supplementary Information (SI) for RSC Mechanochemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_APR_ET
_database_code_depnum_ccdc_archive 'CCDC 2513155'
loop_
_audit_author_name
_audit_author_address
'Rafal Dolot'
;Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences
Poland
;
_audit_update_record             
;
2025-12-03 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_audit_creation_date             2025-12-03
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methanesulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide hemikis(2-ethoxybenzamide)'
_chemical_name_common            'apremilast ethenzamide'
_chemical_formula_moiety         '4(C22 H24 N2 O7 S), C18 H22 N2 O4'
_chemical_formula_sum            'C106 H118 N10 O32 S4'
_chemical_formula_weight         2172.34
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
_chemical_absolute_configuration ad
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'
_exptl_crystal_recrystallization_method 
're-crystallized from acetonitrile after heating and slow cooling'
_chemical_melting_point          ?
_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C H N O S'
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.
;

_cell_length_a                   13.19680(10)
_cell_length_b                   13.19680(10)
_cell_length_c                   29.1386(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5074.65(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    31723
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      79.3910
_cell_measurement_theta_min      3.6680
_shelx_estimated_absorpt_T_max   0.855
_shelx_estimated_absorpt_T_min   0.794
_exptl_absorpt_coefficient_mu    1.614
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.122a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             2288
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0763
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            50488
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.270
_diffrn_reflns_theta_min         3.677
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -31.00   0.50    0.66    --  -47.47 -62.00 109.00  178
  2  ω     32.00  91.00   0.50    0.66    --   47.47-121.00  40.00  118
  3  ω   -163.00 -76.00   0.50    2.65    --  -91.75 -59.00 -84.00  174
  4  ω   -146.00 -54.00   0.50    2.65    --  -91.75-153.00-118.00  184
  5  ω    -73.00 -19.00   0.50    2.65    --  -91.75  62.00-112.00  108
  6  ω     42.00  68.00   0.50    2.65    --  113.25 -59.00 -84.00   52
  7  ω     42.00  73.00   0.50    2.65    --  113.25 -62.00 109.00   62
  8  ω     44.00 110.00   0.50    2.65    --  113.25-121.00  40.00  132
  9  ω   -120.00 -34.00   0.50    0.66    --  -47.47 -38.00 150.00  172
 10  ω    -26.00  28.00   0.50    0.66    --  -47.47  19.00-120.00  108
 11  ω     34.00  93.00   0.50    0.66    --   47.47-125.00 120.00  118
 12  ω   -163.00 -69.00   0.50    2.65    --  -91.75 -77.00-180.00  188
 13  ω     42.00  71.00   0.50    2.65    --  113.25 -61.00 -60.00   58
 14  ω    100.00 178.00   0.50    2.65    --  113.25  15.00-120.00  156
 15  ω     42.00  71.00   0.50    2.65    --  113.25 -61.00  60.00   58
 16  ω     42.00  71.00   0.50    2.65    --  113.25 -61.00-180.00   58
 17  ω    101.00 178.00   0.50    2.65    --  113.25  45.00 150.00  154
 18  ω     97.00 165.00   0.50    2.65    --  113.25  61.00  90.00  136
 19  ω     91.00 171.00   0.50    2.65    --  113.25  77.00 150.00  160
 20  ω     44.00  98.00   0.50    2.65    --  113.25-125.00 -60.00  108
 21  ω    109.00 135.00   0.50    2.65    --  113.25 125.00 -90.00   52
 22  ω     57.00 101.00   0.50    2.65    --  113.25-125.00 -30.00   88
 23  ω     80.00 105.00   0.50    2.65    --  113.25 -77.00-180.00   50
 24  ω    142.00 168.00   0.50    2.65    --  113.25 125.00 -90.00   52
 25  ω    126.00 152.00   0.50    2.65    --  113.25  30.00-180.00   52
 26  ω    149.00 176.00   0.50    2.65    --  113.25  61.00  90.00   54
 27  ω     45.00  70.00   0.50    2.65    --  113.25 -61.00-150.00   50
 28  ω     45.00  71.00   0.50    2.65    --  113.25 -61.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0156501000
_diffrn_orient_matrix_UB_12      0.0845998000
_diffrn_orient_matrix_UB_13      -0.0356752000
_diffrn_orient_matrix_UB_21      -0.1150998000
_diffrn_orient_matrix_UB_22      -0.0026706000
_diffrn_orient_matrix_UB_23      0.0090866000
_diffrn_orient_matrix_UB_31      0.0128057000
_diffrn_orient_matrix_UB_32      0.0802997000
_diffrn_orient_matrix_UB_33      0.0379090000
_diffrn_oxdiff_digest_hkl        
;
437baf1ab063e61f42ba0848748618e61cec63
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.709
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                5341
_reflns_number_total             5495
_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 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.122a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 2101 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(9)
_refine_ls_extinction_coef       0.00045(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         5495
_refine_ls_number_restraints     141
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.066
_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)+(0.0319P)²+3.5871P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0984
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O32-C32
 1.51 with sigma of 0.02
 C32-C33 = C32-C31 = C34-C35
 1.39 with sigma of 0.02
 C33-C34 = C35-C36 = C36-C31
 1.38 with sigma of 0.02
 C39-H39B
 0.98 with sigma of 0.02
 C39-H39A
 0.98 with sigma of 0.02
 C39-H39C
 0.98 with sigma of 0.02
 C38-H38A
 0.99 with sigma of 0.02
 C38-H38B
 0.99 with sigma of 0.02
 O32-C33 = O32-C31
 2.52 with sigma of 0.04
 C32-C34
 2.42 with sigma of 0.04
 C32-C36
 2.41 with sigma of 0.04
 C33-C35
 2.39 with sigma of 0.04
 C34-C36 = C35-C31
 2.4 with sigma of 0.04
 C32-C33 \\sim C33-C34 \\sim C34-C35 \\sim C35-C36 \\sim C36-C31 \\sim C31-C32
 with sigma of 0.02
 C32-C36 \\sim C32-C34 \\sim C31-C35 \\sim C33-C31 \\sim C34-C36 \\sim C33-C35
 with sigma of 0.04
 O32-C31 \\sim O32-C33
 with sigma of 0.04
3. Restrained planarity
 O32, C32, C33, C34, C35, C36, C31
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O32 \\sim C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C31: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
5. Rigid body (RIGU) restrains
 O32, C32, C33, C34, C35, C36, C31
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Fixed Sof: O31(0.5) H39A(0.5) O32(0.5) N31(0.5) H31A(0.5) H31B(0.5) C37(0.5)
 C38(0.5) H38A(0.5) H38B(0.5) C32(0.5) C33(0.5) H33(0.5) C34(0.5) H34(0.5)
 C35(0.5) H35(0.5) C36(0.5) H36(0.5) C31(0.5) C39(0.5) H39B(0.5) H39C(0.5)
7.a Ternary CH refined with riding coordinates:
 C11(H11)
7.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C20(H20A,H20B)
7.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C2(H2A), C18(H18), C3(H3), C4(H4), C33(H33), C34(H34),
 C35(H35), C36(H36)
7.d X=CH2 refined with riding coordinates:
 N31(H31A,H31B)
7.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C22(H22A,H22B,H22C), C13(H13A,H13B,H13C), C21(H21A,H21B,
 H21C)
;
_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 0.41178(5) 0.17263(5) 0.46679(2) 0.02772(17) Uani 1 1 d . . . . .
O1 O 0.41613(17) 0.47405(15) 0.44426(7) 0.0298(4) Uani 1 1 d . . . . .
O2 O 0.48413(17) 0.23684(16) 0.33388(7) 0.0315(5) Uani 1 1 d . . . . .
O4 O 0.45340(18) 0.08480(17) 0.44455(8) 0.0367(5) Uani 1 1 d . . . . .
O5 O 0.32253(17) 0.21787(17) 0.44689(8) 0.0345(5) Uani 1 1 d . . . . .
O3 O 0.20573(19) 0.30758(19) 0.20978(7) 0.0389(5) Uani 1 1 d . . . . .
O6 O 0.76209(18) 0.55131(19) 0.50966(8) 0.0397(6) Uani 1 1 d . . . . .
O7 O 0.89759(18) 0.5493(2) 0.44460(9) 0.0458(6) Uani 1 1 d . . . . .
N1 N 0.47083(19) 0.34609(18) 0.39600(8) 0.0250(5) Uani 1 1 d . . . . .
N2 N 0.3262(2) 0.2871(2) 0.26529(8) 0.0298(5) Uani 1 1 d . . . . .
H2 H 0.376(3) 0.254(2) 0.2742(11) 0.017(8) Uiso 1 1 d . . . . .
C7 C 0.4420(2) 0.3069(2) 0.35321(9) 0.0249(6) Uani 1 1 d . . . . .
C6 C 0.4081(2) 0.4261(2) 0.40903(9) 0.0252(6) Uani 1 1 d . . . . .
C8 C 0.3539(2) 0.3667(2) 0.33801(9) 0.0249(6) Uani 1 1 d . . . . .
C1 C 0.2972(2) 0.3594(2) 0.29793(10) 0.0282(6) Uani 1 1 d . . . . .
C12 C 0.5071(2) 0.2664(2) 0.47142(9) 0.0269(6) Uani 1 1 d . . . . .
H12A H 0.478562 0.326259 0.487286 0.032 Uiso 1 1 calc R U . . .
H12B H 0.563002 0.239646 0.490544 0.032 Uiso 1 1 calc R U . . .
C9 C 0.2838(3) 0.2671(2) 0.22333(10) 0.0340(7) Uani 1 1 d . . . . .
C14 C 0.6420(2) 0.3673(2) 0.43047(10) 0.0275(6) Uani 1 1 d . . . . .
C5 C 0.3322(2) 0.4388(2) 0.37143(9) 0.0281(6) Uani 1 1 d . . . . .
C15 C 0.6566(2) 0.4282(2) 0.46926(10) 0.0271(6) Uani 1 1 d . . . . .
H15 H 0.607587 0.427966 0.493143 0.033 Uiso 1 1 calc R U . . .
C20 C 0.6894(2) 0.5535(3) 0.54612(11) 0.0353(7) Uani 1 1 d . . . . .
H20A H 0.687929 0.487239 0.562055 0.042 Uiso 1 1 calc R U . . .
H20B H 0.620954 0.567271 0.533693 0.042 Uiso 1 1 calc R U . . .
C11 C 0.5500(2) 0.2997(2) 0.42496(9) 0.0256(6) Uani 1 1 d . . . . .
H11 H 0.573197 0.236964 0.408822 0.031 Uiso 1 1 calc R U . . .
C19 C 0.7139(2) 0.3675(3) 0.39623(11) 0.0352(7) Uani 1 1 d . . . . .
H19 H 0.704757 0.325626 0.370027 0.042 Uiso 1 1 calc R U . . .
C2 C 0.2157(3) 0.4266(2) 0.29327(11) 0.0346(7) Uani 1 1 d . . . . .
H2A H 0.174439 0.423941 0.266578 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8002(2) 0.4284(3) 0.39959(11) 0.0366(7) Uani 1 1 d . . . . .
H18 H 0.848728 0.428676 0.375517 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8149(2) 0.4884(3) 0.43794(11) 0.0338(7) Uani 1 1 d . . . . .
C16 C 0.7422(2) 0.4888(2) 0.47310(10) 0.0308(6) Uani 1 1 d . . . . .
C3 C 0.1946(3) 0.4975(3) 0.32748(12) 0.0414(8) Uani 1 1 d . . . . .
H3 H 0.138586 0.541875 0.323485 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2527(3) 0.5058(3) 0.36743(11) 0.0364(7) Uani 1 1 d . . . . .
H4 H 0.238219 0.554755 0.390433 0.044 Uiso 1 1 calc R U . . .
C10 C 0.3423(3) 0.1921(3) 0.19519(11) 0.0435(8) Uani 1 1 d . . . . .
H10A H 0.302352 0.172767 0.168226 0.065 Uiso 1 1 calc R U . . .
H10B H 0.356530 0.131801 0.213724 0.065 Uiso 1 1 calc R U . . .
H10C H 0.406255 0.222768 0.185230 0.065 Uiso 1 1 calc R U . . .
C22 C 0.9723(3) 0.5480(4) 0.40871(13) 0.0556(11) Uani 1 1 d . . . . .
H22A H 0.942676 0.575398 0.380472 0.083 Uiso 1 1 calc R U . . .
H22B H 0.994618 0.478154 0.403349 0.083 Uiso 1 1 calc R U . . .
H22C H 1.030446 0.589509 0.417828 0.083 Uiso 1 1 calc R U . . .
C13 C 0.3860(3) 0.1438(3) 0.52448(11) 0.0399(8) Uani 1 1 d . . . . .
H13A H 0.334760 0.090090 0.525990 0.060 Uiso 1 1 calc R U . . .
H13B H 0.360509 0.204431 0.540085 0.060 Uiso 1 1 calc R U . . .
H13C H 0.448219 0.120698 0.539546 0.060 Uiso 1 1 calc R U . . .
C21 C 0.7197(3) 0.6356(3) 0.57901(14) 0.0550(11) Uani 1 1 d . . . . .
H21A H 0.725244 0.700072 0.562491 0.083 Uiso 1 1 calc R U . . .
H21B H 0.785190 0.618724 0.592854 0.083 Uiso 1 1 calc R U . . .
H21C H 0.668308 0.641703 0.603144 0.083 Uiso 1 1 calc R U . . .
O31 O 0.3188(7) 0.5443(6) 0.1550(2) 0.0583(16) Uani 0.5 1 d . . P . .
H39A H 0.445(6) 0.746(7) 0.3733(18) 0.05(2) Uiso 0.5 1 d D . P A -1
O32 O 0.4243(4) 0.6007(4) 0.28623(16) 0.0375(10) Uani 0.5 1 d D U P B -1
N31 N 0.2782(5) 0.6116(5) 0.2234(2) 0.0460(15) Uani 0.5 1 d . . P B -1
H31A H 0.223428 0.640171 0.212096 0.055 Uiso 0.5 1 calc R U P B -1
H31B H 0.293428 0.619326 0.252618 0.055 Uiso 0.5 1 calc R U P B -1
C37 C 0.3380(6) 0.5568(6) 0.1964(3) 0.0417(16) Uani 0.5 1 d . . P B -1
C38 C 0.4775(7) 0.6347(7) 0.3256(4) 0.0405(16) Uani 0.5 1 d D . P B -1
H38A H 0.548(3) 0.655(6) 0.318(3) 0.05(2) Uiso 0.5 1 d D . P C -1
H38B H 0.493(7) 0.578(5) 0.348(2) 0.06(3) Uiso 0.5 1 d D . P D -1
C32 C 0.4698(6) 0.5261(6) 0.26042(19) 0.0366(17) Uani 0.5 1 d D U P B -1
C33 C 0.5548(5) 0.4740(5) 0.2769(2) 0.0360(14) Uani 0.5 1 d D U P B -1
H33 H 0.580853 0.488054 0.306610 0.043 Uiso 0.5 1 calc R U P B -1
C34 C 0.600(2) 0.402(2) 0.2492(8) 0.0414(15) Uani 0.5 1 d D U P B -1
H34 H 0.660121 0.368390 0.259279 0.050 Uiso 0.5 1 calc R U P B -1
C35 C 0.5585(6) 0.3777(6) 0.2068(3) 0.0504(18) Uani 0.5 1 d D U P B -1
H35 H 0.585654 0.323755 0.189123 0.060 Uiso 0.5 1 calc R U P B -1
C36 C 0.4764(5) 0.4335(5) 0.1904(2) 0.0418(15) Uani 0.5 1 d D U P B -1
H36 H 0.452314 0.420376 0.160290 0.050 Uiso 0.5 1 calc R U P B -1
C31 C 0.4291(6) 0.5063(6) 0.2161(2) 0.0402(15) Uani 0.5 1 d D U P B -1
C39 C 0.4089(8) 0.7216(7) 0.3447(3) 0.0451(19) Uani 0.5 1 d D . P B -1
H39B H 0.386(5) 0.773(4) 0.321(2) 0.035(19) Uiso 0.5 1 d D . P E -1
H39C H 0.340(3) 0.697(5) 0.355(2) 0.04(2) Uiso 0.5 1 d D . P F -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 O4 1.437(2) . ?
S1 O5 1.442(2) . ?
S1 C12 1.769(3) . ?
S1 C13 1.757(3) . ?
O1 C6 1.211(3) . ?
O2 C7 1.217(3) . ?
O3 C9 1.226(4) . ?
O6 C20 1.432(4) . ?
O6 C16 1.372(4) . ?
O7 C17 1.369(4) . ?
O7 C22 1.437(4) . ?
N1 C7 1.402(3) . ?
N1 C6 1.395(4) . ?
N1 C11 1.476(4) . ?
N2 H2 0.83(3) . ?
N2 C1 1.401(4) . ?
N2 C9 1.371(4) . ?
C7 C8 1.473(4) . ?
C6 C5 1.493(4) . ?
C8 C1 1.390(4) . ?
C8 C5 1.391(4) . ?
C1 C2 1.401(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.532(4) . ?
C9 C10 1.499(5) . ?
C14 C15 1.400(4) . ?
C14 C11 1.516(4) . ?
C14 C19 1.377(4) . ?
C5 C4 1.378(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.390(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.501(5) . ?
C11 H11 1.0000 . ?
C19 H19 0.9500 . ?
C19 C18 1.398(5) . ?
C2 H2A 0.9500 . ?
C2 C3 1.395(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(5) . ?
C17 C16 1.403(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(5) . ?
C4 H4 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O31 C37 1.245(11) . ?
O32 C38 1.418(11) . ?
O32 C32 1.377(8) . ?
N31 H31A 0.8800 . ?
N31 H31B 0.8800 . ?
N31 C37 1.328(12) . ?
C37 C31 1.488(11) . ?
C38 H38A 0.99(3) . ?
C38 H38B 1.01(3) . ?
C38 C39 1.563(12) . ?
C32 C33 1.400(8) . ?
C32 C31 1.423(9) . ?
C33 H33 0.9500 . ?
C33 C34 1.387(10) . ?
C34 H34 0.9500 . ?
C34 C35 1.389(14) . ?
C35 H35 0.9500 . ?
C35 C36 1.394(9) . ?
C36 H36 0.9500 . ?
C36 C31 1.368(9) . ?
C39 H39A 1.01(3) . ?
C39 H39B 1.00(3) . ?
C39 H39C 1.02(3) . ?

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
O4 S1 O5 117.69(14) . . ?
O4 S1 C12 109.07(14) . . ?
O4 S1 C13 109.31(17) . . ?
O5 S1 C12 108.76(14) . . ?
O5 S1 C13 108.42(16) . . ?
C13 S1 C12 102.50(15) . . ?
C16 O6 C20 117.4(2) . . ?
C17 O7 C22 115.9(3) . . ?
C7 N1 C11 123.2(2) . . ?
C6 N1 C7 111.1(2) . . ?
C6 N1 C11 125.4(2) . . ?
C1 N2 H2 111(2) . . ?
C9 N2 H2 120(2) . . ?
C9 N2 C1 128.7(3) . . ?
O2 C7 N1 124.6(3) . . ?
O2 C7 C8 128.9(3) . . ?
N1 C7 C8 106.5(2) . . ?
O1 C6 N1 125.1(3) . . ?
O1 C6 C5 128.5(3) . . ?
N1 C6 C5 106.5(2) . . ?
C1 C8 C7 129.8(3) . . ?
C1 C8 C5 121.6(3) . . ?
C5 C8 C7 108.6(2) . . ?
N2 C1 C2 125.1(3) . . ?
C8 C1 N2 118.1(3) . . ?
C8 C1 C2 116.8(3) . . ?
S1 C12 H12A 108.9 . . ?
S1 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C11 C12 S1 113.3(2) . . ?
C11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
O3 C9 N2 123.1(3) . . ?
O3 C9 C10 123.0(3) . . ?
N2 C9 C10 113.9(3) . . ?
C15 C14 C11 122.3(3) . . ?
C19 C14 C15 119.3(3) . . ?
C19 C14 C11 118.4(3) . . ?
C8 C5 C6 107.4(2) . . ?
C4 C5 C6 130.1(3) . . ?
C4 C5 C8 122.5(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.8 . . ?
O6 C20 H20A 110.1 . . ?
O6 C20 H20B 110.1 . . ?
O6 C20 C21 108.1(3) . . ?
H20A C20 H20B 108.4 . . ?
C21 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
N1 C11 C12 111.3(2) . . ?
N1 C11 C14 112.5(2) . . ?
N1 C11 H11 106.9 . . ?
C12 C11 H11 106.9 . . ?
C14 C11 C12 111.8(2) . . ?
C14 C11 H11 106.9 . . ?
C14 C19 H19 119.6 . . ?
C14 C19 C18 120.8(3) . . ?
C18 C19 H19 119.6 . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2A 119.7 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
O7 C17 C18 124.2(3) . . ?
O7 C17 C16 116.1(3) . . ?
C18 C17 C16 119.7(3) . . ?
O6 C16 C15 124.3(3) . . ?
O6 C16 C17 116.0(3) . . ?
C15 C16 C17 119.7(3) . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.6(3) . . ?
C4 C3 H3 118.7 . . ?
C5 C4 C3 116.0(3) . . ?
C5 C4 H4 122.0 . . ?
C3 C4 H4 122.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
S1 C13 H13A 109.5 . . ?
S1 C13 H13B 109.5 . . ?
S1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C32 O32 C38 116.8(6) . . ?
H31A N31 H31B 120.0 . . ?
C37 N31 H31A 120.0 . . ?
C37 N31 H31B 120.0 . . ?
O31 C37 N31 121.7(9) . . ?
O31 C37 C31 118.6(10) . . ?
N31 C37 C31 119.7(8) . . ?
O32 C38 H38A 112(5) . . ?
O32 C38 H38B 112(5) . . ?
O32 C38 C39 103.4(7) . . ?
H38A C38 H38B 99(7) . . ?
C39 C38 H38A 115(5) . . ?
C39 C38 H38B 116(5) . . ?
O32 C32 C33 120.9(6) . . ?
O32 C32 C31 117.5(6) . . ?
C33 C32 C31 121.6(6) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 C32 119.1(7) . . ?
C34 C33 H33 120.5 . . ?
C33 C34 H34 119.9 . . ?
C33 C34 C35 120.1(8) . . ?
C35 C34 H34 119.9 . . ?
C34 C35 H35 120.2 . . ?
C34 C35 C36 119.6(7) . . ?
C36 C35 H35 120.2 . . ?
C35 C36 H36 118.7 . . ?
C31 C36 C35 122.5(7) . . ?
C31 C36 H36 118.7 . . ?
C32 C31 C37 124.9(7) . . ?
C36 C31 C37 118.2(7) . . ?
C36 C31 C32 116.9(7) . . ?
H39A C39 H39B 119(7) . . ?
H39A C39 H39C 105(6) . . ?
C38 C39 H39A 105(5) . . ?
C38 C39 H39B 115(4) . . ?
C38 C39 H39C 113(4) . . ?
H39B C39 H39C 99(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O3 0.95 2.30 2.899(4) 120.8 . yes
N31 H31B O32 0.88 2.00 2.661(8) 131.0 . yes

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 C12 C11 N1 62.1(3) . . . . ?
S1 C12 C11 C14 -171.1(2) . . . . ?
O1 C6 C5 C8 179.5(3) . . . . ?
O1 C6 C5 C4 -1.0(5) . . . . ?
O2 C7 C8 C1 -0.6(5) . . . . ?
O2 C7 C8 C5 179.8(3) . . . . ?
O4 S1 C12 C11 59.7(2) . . . . ?
O5 S1 C12 C11 -69.8(2) . . . . ?
O7 C17 C16 O6 0.9(4) . . . . ?
O7 C17 C16 C15 -179.2(3) . . . . ?
N1 C7 C8 C1 179.4(3) . . . . ?
N1 C7 C8 C5 -0.2(3) . . . . ?
N1 C6 C5 C8 -0.4(3) . . . . ?
N1 C6 C5 C4 179.1(3) . . . . ?
N2 C1 C2 C3 -178.5(3) . . . . ?
C7 N1 C6 O1 -179.6(3) . . . . ?
C7 N1 C6 C5 0.3(3) . . . . ?
C7 N1 C11 C12 -119.2(3) . . . . ?
C7 N1 C11 C14 114.4(3) . . . . ?
C7 C8 C1 N2 -1.7(5) . . . . ?
C7 C8 C1 C2 179.1(3) . . . . ?
C7 C8 C5 C6 0.4(3) . . . . ?
C7 C8 C5 C4 -179.2(3) . . . . ?
C6 N1 C7 O2 179.9(3) . . . . ?
C6 N1 C7 C8 -0.1(3) . . . . ?
C6 N1 C11 C12 53.4(4) . . . . ?
C6 N1 C11 C14 -73.0(3) . . . . ?
C6 C5 C4 C3 -179.6(3) . . . . ?
C8 C1 C2 C3 0.6(5) . . . . ?
C8 C5 C4 C3 -0.2(5) . . . . ?
C1 N2 C9 O3 -5.9(5) . . . . ?
C1 N2 C9 C10 173.3(3) . . . . ?
C1 C8 C5 C6 -179.3(3) . . . . ?
C1 C8 C5 C4 1.2(5) . . . . ?
C1 C2 C3 C4 0.4(6) . . . . ?
C9 N2 C1 C8 -178.8(3) . . . . ?
C9 N2 C1 C2 0.4(5) . . . . ?
C14 C15 C16 O6 179.4(3) . . . . ?
C14 C15 C16 C17 -0.5(5) . . . . ?
C14 C19 C18 C17 1.0(5) . . . . ?
C5 C8 C1 N2 177.8(3) . . . . ?
C5 C8 C1 C2 -1.4(4) . . . . ?
C15 C14 C11 N1 98.6(3) . . . . ?
C15 C14 C11 C12 -27.5(4) . . . . ?
C15 C14 C19 C18 -0.8(5) . . . . ?
C20 O6 C16 C15 0.1(5) . . . . ?
C20 O6 C16 C17 180.0(3) . . . . ?
C11 N1 C7 O2 -6.5(4) . . . . ?
C11 N1 C7 C8 173.5(2) . . . . ?
C11 N1 C6 O1 7.0(4) . . . . ?
C11 N1 C6 C5 -173.1(2) . . . . ?
C11 C14 C15 C16 179.7(3) . . . . ?
C11 C14 C19 C18 180.0(3) . . . . ?
C19 C14 C15 C16 0.6(5) . . . . ?
C19 C14 C11 N1 -82.2(3) . . . . ?
C19 C14 C11 C12 151.7(3) . . . . ?
C19 C18 C17 O7 178.9(3) . . . . ?
C19 C18 C17 C16 -0.9(5) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C18 C17 C16 O6 -179.3(3) . . . . ?
C18 C17 C16 C15 0.6(5) . . . . ?
C16 O6 C20 C21 -172.9(3) . . . . ?
C22 O7 C17 C18 -0.3(5) . . . . ?
C22 O7 C17 C16 179.5(3) . . . . ?
C13 S1 C12 C11 175.5(2) . . . . ?
O31 C37 C31 C32 169.3(7) . . . . ?
O31 C37 C31 C36 -12.3(11) . . . . ?
O32 C32 C33 C34 -178(2) . . . . ?
O32 C32 C31 C37 -3.0(10) . . . . ?
O32 C32 C31 C36 178.6(6) . . . . ?
N31 C37 C31 C32 -12.3(11) . . . . ?
N31 C37 C31 C36 166.0(7) . . . . ?
C38 O32 C32 C33 11.3(9) . . . . ?
C38 O32 C32 C31 -167.0(7) . . . . ?
C32 O32 C38 C39 176.9(6) . . . . ?
C32 C33 C34 C35 -3(4) . . . . ?
C33 C32 C31 C37 178.8(7) . . . . ?
C33 C32 C31 C36 0.4(10) . . . . ?
C33 C34 C35 C36 6(4) . . . . ?
C34 C35 C36 C31 -6(2) . . . . ?
C35 C36 C31 C37 -176.2(7) . . . . ?
C35 C36 C31 C32 2.3(10) . . . . ?
C31 C32 C33 C34 0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
'mounted on a nylon cryo-loop with mineral oil as a cryoprotectant'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.322
_oxdiff_exptl_absorpt_empirical_full_min 0.636

