# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_dm18o_0m
_audit_block_doi                 10.5517/ccdc.csd.cc22fhkl
_database_code_depnum_ccdc_archive 'CCDC 1919599'
loop_
_audit_author_name
_audit_author_address
'Evan Vanable'
;University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2019-05-29 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2019-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
loop_
_audit_author_email
?
evanvanable@gmail.com
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(C19 H26 N2), 4(C10 H6 O6 S2)'
_chemical_formula_sum            'C116 H128 N8 O24 S8'
_chemical_formula_weight         2274.88
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 0.32300 0.14000 0.04100 10.51100 26.12600 3.14200
57.80000 0.003 'Custom 4-Gaussian' custom
C 0.00300 0.00200 2.31000 1.02000 1.58900 0.86500 20.84400 10.20800 0.56900
51.65100 0.216 'Custom 4-Gaussian' custom
S 0.12500 0.12300 6.90500 5.20300 1.43800 1.58600 1.46800 22.21500 0.25400
56.17200 0.867 'Custom 4-Gaussian' custom
O 0.01100 0.00600 3.04900 2.28700 1.54600 0.86700 13.27700 5.70100 0.32400
32.90900 0.251 'Custom 4-Gaussian' custom
N 0.00600 0.00300 12.21300 3.13200 2.01300 1.16600 0.00600 9.89300 28.99800
0.58300 -11.529 'Custom 4-Gaussian' custom

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.6273(6)
_cell_length_b                   11.1454(4)
_cell_length_c                   21.3411(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.896(2)
_cell_angle_gamma                90
_cell_volume                     3592.1(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    12315
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.75
_cell_measurement_theta_min      2.27
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.0684 before and 0.0635 after correction.
The Ratio of minimum to maximum transmission is 0.9057.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.0515
_exptl_crystal_description       prism
_exptl_crystal_F_000             1201.6128
_exptl_crystal_preparation       
"1/2 equivalent of Armstrong's Acid was added to 0.05 mmol of the diamine dissolved in 1 mL ethanol. This was then layered with ethyl acetate, and after a weeks time crystals suitable for diffraction were observed."
_exptl_crystal_recrystallization_method 
'Layered crystallization of 0.02 mmol in 0.2 mL ethanol with 0.2 mL fresh ethanol and 0.6 mL ethyl acetate, allowed to sit for two weeks without disturbing to obtain X-ray quality crystals.'
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.119
_exptl_crystal_size_min          0.104
_diffrn_reflns_av_R_equivalents  0.0692
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            72162
_diffrn_reflns_theta_full        25.3963
_diffrn_reflns_theta_max         25.40
_diffrn_reflns_theta_min         1.97
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9973
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              18
_reflns_limit_h_min              -18
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              25
_reflns_limit_l_min              0
_reflns_number_gt                4856
_reflns_number_total             6586
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.5014
_refine_diff_density_min         -0.6498
_refine_diff_density_rms         0.0835
_refine_ls_d_res_high            0.8286
_refine_ls_d_res_low             10.3120
_refine_ls_goodness_of_fit_ref   1.0911
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    70
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6586
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0528
_refine_ls_restrained_S_all      1.0885
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0894P)²+3.8982P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.1824
_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 N(H,H) groups, All N(H,H,H) groups
2. Restrained distances
 C22-C1AA \\sim C22-C1AB
 with sigma of 0.02
 C1AA-C2AA \\sim C1AB-C2AB
 with sigma of 0.02
 C1AA-C0AA \\sim C1AB-C0AB
 with sigma of 0.02
 C2AA-C5AA \\sim C2AB-C5AB
 with sigma of 0.02
 C3AA-C5AA \\sim C3AB-C5AB
 with sigma of 0.02
 C3AA-C4AA \\sim C3AB-C4AB
 with sigma of 0.02
 C0AA-C4AA \\sim C0AB-C4AB
 with sigma of 0.02
 C22-C2AA \\sim C22-C2AB
 with sigma of 0.04
 C22-C0AA \\sim C22-C0AB
 with sigma of 0.04
 C1AA-C5AA \\sim C1AB-C5AB
 with sigma of 0.04
 C1AA-C4AA \\sim C1AB-C4AB
 with sigma of 0.04
 C2AA-C3AA \\sim C2AB-C3AB
 with sigma of 0.04
 C2AA-C0AA \\sim C2AB-C0AB
 with sigma of 0.04
 C3AA-C0AA \\sim C3AB-C0AB
 with sigma of 0.04
 C5AA-C4AA \\sim C5AB-C4AB
 with sigma of 0.04
3. Others
 Sof(H22a)=Sof(C2AB)=Sof(H2AB)=Sof(C1AB)=Sof(C0AB)=Sof(H0AB)=Sof(C4AB)=
 Sof(H4AB)=Sof(C3AB)=Sof(H3AB)=Sof(C5AB)=Sof(H5AB)=1-FVAR(1)
 Sof(H22)=Sof(C1AA)=Sof(C2AA)=Sof(H2AA)=Sof(C3AA)=Sof(H3AA)=Sof(C0AA)=
 Sof(H0AA)=Sof(C5AA)=Sof(H5AA)=Sof(C4AA)=Sof(H4AA)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C22(H22), C22(H22a), C23(H23), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 N2(H2a,H2b), C24(H24a,H24b), C32(H32a,H32b), C33(H33a,H33b), C34(H34a,H34b)
4.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C10(H10), C9(H9), C8(H8),
 C5(H5), C6(H6), C7(H7), C2AA(H2AA), C3AA(H3AA), C0AA(H0AA), C5AA(H5AA),
 C4AA(H4AA), C2AB(H2AB), C0AB(H0AB), C4AB(H4AB), C3AB(H3AB), C5AB(H5AB)
4.d Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c)
;
_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
_atom_site_disorder_group
N1 N 0.31636(17) 0.5885(2) 0.55561(12) 0.0307(6) Uani 1.000000 . .
H1a H 0.2734(9) 0.5582(3) 0.5222(6) 0.0461(9) Uiso 1.000000 GR .
H1b H 0.3705(5) 0.5678(2) 0.5505(10) 0.0461(9) Uiso 1.000000 GR .
H1c H 0.3099(14) 0.5581(3) 0.5937(4) 0.0461(9) Uiso 1.000000 GR .
N2 N 0.61175(15) 0.7425(2) 0.61454(11) 0.0234(5) Uani 1.000000 . .
H2a H 0.63368(15) 0.7774(2) 0.65452(11) 0.0351(8) Uiso 1.000000 R .
H2b H 0.61223(15) 0.6608(2) 0.62060(11) 0.0351(8) Uiso 1.000000 R .
C22 C 0.3086(2) 0.7230(3) 0.55640(16) 0.0332(7) Uani 1.000000 D .
H22 H 0.3205(2) 0.7587(3) 0.51648(16) 0.0399(9) Uiso 0.44(2) R 1
H22a H 0.3318(2) 0.7521(3) 0.51960(16) 0.0399(9) Uiso 0.56(2) R 2
C23 C 0.3691(2) 0.7797(3) 0.61774(16) 0.0349(7) Uani 1.000000 . .
H23 H 0.3442(2) 0.7582(3) 0.65500(16) 0.0419(9) Uiso 1.000000 R .
C24 C 0.4657(2) 0.7386(3) 0.63498(14) 0.0294(7) Uani 1.000000 . .
H24a H 0.4955(2) 0.7678(3) 0.67901(14) 0.0353(8) Uiso 1.000000 R .
H24b H 0.4674(2) 0.6498(3) 0.63599(14) 0.0353(8) Uiso 1.000000 R .
C25 C 0.51662(18) 0.7827(3) 0.58804(13) 0.0248(6) Uani 1.000000 . .
H25 H 0.49162(18) 0.7460(3) 0.54441(13) 0.0298(7) Uiso 1.000000 R .
C32 C 0.5132(2) 0.9196(3) 0.58241(15) 0.0302(7) Uani 1.000000 . .
H32a H 0.5453(2) 0.9558(3) 0.62422(15) 0.0363(8) Uiso 1.000000 R .
H32b H 0.5426(2) 0.9457(3) 0.54879(15) 0.0363(8) Uiso 1.000000 R .
C33 C 0.4171(2) 0.9630(3) 0.56450(18) 0.0379(8) Uani 1.000000 . .
H33a H 0.4161(2) 1.0518(3) 0.56405(18) 0.0454(9) Uiso 1.000000 R .
H33b H 0.3872(2) 0.9346(3) 0.52034(18) 0.0454(9) Uiso 1.000000 R .
C34 C 0.3670(2) 0.9177(3) 0.61190(18) 0.0404(8) Uani 1.000000 . .
H34a H 0.3047(2) 0.9447(3) 0.59750(18) 0.0485(10) Uiso 1.000000 R .
H34b H 0.3932(2) 0.9531(3) 0.65511(18) 0.0485(10) Uiso 1.000000 R .
C27 C 0.65678(19) 0.7182(3) 0.51324(14) 0.0258(6) Uani 1.000000 . .
H27 H 0.60843(19) 0.6650(3) 0.49798(14) 0.0310(8) Uiso 1.000000 R .
C28 C 0.7144(2) 0.7445(3) 0.47545(16) 0.0340(7) Uani 1.000000 . .
H28 H 0.7052(2) 0.7095(3) 0.43367(16) 0.0408(9) Uiso 1.000000 R .
C29 C 0.7846(2) 0.8209(3) 0.49791(19) 0.0432(9) Uani 1.000000 . .
H29 H 0.8235(2) 0.8384(3) 0.47150(19) 0.0519(10) Uiso 1.000000 R .
C30 C 0.7990(2) 0.8724(3) 0.55860(19) 0.0453(9) Uani 1.000000 . .
H30 H 0.8478(2) 0.9249(3) 0.57395(19) 0.0544(11) Uiso 1.000000 R .
C31 C 0.7417(2) 0.8472(3) 0.59719(17) 0.0363(8) Uani 1.000000 . .
H31 H 0.7511(2) 0.8818(3) 0.63908(17) 0.0435(9) Uiso 1.000000 R .
C26 C 0.67127(18) 0.7712(2) 0.57379(14) 0.0244(6) Uani 1.000000 . .
S1 S 0.56699(5) 0.41446(7) 0.60022(3) 0.0333(2) Uani 1.000000 . .
S2 S 0.72767(6) -0.08726(7) 0.78081(3) 0.0363(2) Uani 1.000000 . .
O1 O 0.63067(17) 0.5015(2) 0.63525(12) 0.0509(7) Uani 1.000000 . .
O2 O 0.47674(15) 0.4582(2) 0.58648(10) 0.0380(6) Uani 1.000000 . .
O3 O 0.59040(15) 0.3676(2) 0.54364(10) 0.0382(5) Uani 1.000000 . .
O4 O 0.7050(2) -0.0521(2) 0.84044(10) 0.0545(7) Uani 1.000000 . .
O5 O 0.65859(15) -0.16228(19) 0.74049(9) 0.0339(5) Uani 1.000000 . .
O6 O 0.81485(16) -0.1375(2) 0.79075(12) 0.0484(6) Uani 1.000000 . .
C1 C 0.5715(2) 0.2903(3) 0.65350(13) 0.0319(7) Uani 1.000000 . .
C10 C 0.4967(2) 0.2620(3) 0.67175(14) 0.0361(8) Uani 1.000000 . .
H10 H 0.4452(2) 0.3102(3) 0.65761(14) 0.0433(9) Uiso 1.000000 R .
C9 C 0.4954(2) 0.1617(3) 0.71146(15) 0.0392(8) Uani 1.000000 . .
H9 H 0.4428(2) 0.1425(3) 0.72384(15) 0.0470(10) Uiso 1.000000 R .
C8 C 0.5687(2) 0.0919(3) 0.73236(15) 0.0383(8) Uani 1.000000 . .
H8 H 0.5666(2) 0.0242(3) 0.75897(15) 0.0459(10) Uiso 1.000000 R .
C3 C 0.6481(2) 0.1191(3) 0.71485(13) 0.0326(7) Uani 1.000000 . .
C4 C 0.7274(2) 0.0472(3) 0.73510(14) 0.0319(7) Uani 1.000000 . .
C5 C 0.8021(2) 0.0772(3) 0.71735(16) 0.0385(8) Uani 1.000000 . .
H5 H 0.8539(2) 0.0295(3) 0.73167(16) 0.0462(10) Uiso 1.000000 R .
C6 C 0.8036(2) 0.1773(3) 0.67824(18) 0.0439(9) Uani 1.000000 . .
H6 H 0.8564(2) 0.1973(3) 0.66640(18) 0.0526(11) Uiso 1.000000 R .
C7 C 0.7297(2) 0.2470(3) 0.65681(16) 0.0408(9) Uani 1.000000 . .
H7 H 0.7315(2) 0.3139(3) 0.62961(16) 0.0490(10) Uiso 1.000000 R .
C2 C 0.6508(2) 0.2206(3) 0.67461(14) 0.0314(7) Uani 1.000000 . .
C1AA C 0.2162(10) 0.7592(16) 0.5626(8) 0.022(3) Uani 0.44(2) D 1
C2AA C 0.1624(10) 0.8184(15) 0.5130(8) 0.048(4) Uani 0.44(2) D 1
H2AA H 0.1852(10) 0.8420(15) 0.4777(8) 0.058(4) Uiso 0.44(2) R 1
C3AA C 0.0439(9) 0.8171(17) 0.5596(12) 0.060(5) Uani 0.44(2) D 1
H3AA H -0.0145(9) 0.8405(17) 0.5597(12) 0.072(6) Uiso 0.44(2) R 1
C0AA C 0.1821(8) 0.7222(9) 0.6141(8) 0.031(3) Uani 0.44(2) D 1
H0AA H 0.2182(8) 0.6785(9) 0.6493(8) 0.037(4) Uiso 0.44(2) R 1
C5AA C 0.0748(12) 0.8470(18) 0.5108(10) 0.057(5) Uani 0.44(2) D 1
H5AA H 0.0385(12) 0.8874(18) 0.4743(10) 0.069(6) Uiso 0.44(2) R 1
C4AA C 0.0953(7) 0.7500(11) 0.6133(10) 0.049(4) Uani 0.44(2) D 1
H4AA H 0.0707(7) 0.7251(11) 0.6475(10) 0.059(4) Uiso 0.44(2) R 1
C2AB C 0.1714(6) 0.8246(8) 0.4867(7) 0.029(2) Uani 0.56(2) D 2
H2AB H 0.2043(6) 0.8463(8) 0.4567(7) 0.035(3) Uiso 0.56(2) R 2
C1AB C 0.2099(8) 0.7551(13) 0.5380(7) 0.026(2) Uani 0.56(2) D 2
C0AB C 0.1618(8) 0.7245(9) 0.5826(8) 0.042(3) Uani 0.56(2) D 2
H0AB H 0.1881(8) 0.6766(9) 0.6193(8) 0.051(3) Uiso 0.56(2) R 2
C4AB C 0.0748(8) 0.7649(10) 0.5726(10) 0.054(4) Uani 0.56(2) D 2
H4AB H 0.0416(8) 0.7450(10) 0.6028(10) 0.065(5) Uiso 0.56(2) R 2
C3AB C 0.0371(8) 0.8340(11) 0.5187(12) 0.050(4) Uani 0.56(2) D 2
H3AB H -0.0227(8) 0.8597(11) 0.5112(12) 0.060(5) Uiso 0.56(2) R 2
C5AB C 0.0850(5) 0.8650(7) 0.4769(8) 0.043(3) Uani 0.56(2) D 2
H5AB H 0.0595(5) 0.9144(7) 0.4406(8) 0.052(4) Uiso 0.56(2) R 2


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
N1 H1a 0.9100 . ?
N1 H1b 0.9100 . ?
N1 H1c 0.9100 . ?
N1 C22 1.505(4) . ?
N2 H2a 0.9200 . ?
N2 H2b 0.9200 . ?
N2 C25 1.516(3) . ?
N2 C26 1.463(4) . ?
C22 H22 1.0000 . ?
C22 H22a 1.0000 . ?
C22 C23 1.539(5) . ?
C22 C1AA 1.537(16) . ?
C22 C1AB 1.534(13) . ?
C23 H23 1.0000 . ?
C23 C24 1.530(4) . ?
C23 C34 1.543(4) . ?
C24 H24a 0.9900 . ?
C24 H24b 0.9900 . ?
C24 C25 1.512(4) . ?
C25 H25 1.0000 . ?
C25 C32 1.531(4) . ?
C32 H32a 0.9900 . ?
C32 H32b 0.9900 . ?
C32 C33 1.529(4) . ?
C33 H33a 0.9900 . ?
C33 H33b 0.9900 . ?
C33 C34 1.516(5) . ?
C34 H34a 0.9900 . ?
C34 H34b 0.9900 . ?
C27 H27 0.9500 . ?
C27 C28 1.386(4) . ?
C27 C26 1.386(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.374(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(5) . ?
C31 H31 0.9500 . ?
C31 C26 1.376(4) . ?
S1 O1 1.452(3) . ?
S1 O2 1.449(2) . ?
S1 O3 1.446(2) . ?
S1 C1 1.781(3) . ?
S2 O4 1.459(2) . ?
S2 O5 1.459(2) . ?
S2 O6 1.437(3) . ?
S2 C4 1.787(3) . ?
C1 C10 1.360(5) . ?
C1 C2 1.434(4) . ?
C10 H10 0.9500 . ?
C10 C9 1.406(5) . ?
C9 H9 0.9500 . ?
C9 C8 1.361(5) . ?
C8 H8 0.9500 . ?
C8 C3 1.417(5) . ?
C3 C4 1.445(4) . ?
C3 C2 1.428(4) . ?
C4 C5 1.359(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.369(5) . ?
C7 H7 0.9500 . ?
C7 C2 1.411(5) . ?
C1AA C2AA 1.343(17) . ?
C1AA C0AA 1.402(17) . ?
C2AA H2AA 0.9500 . ?
C2AA C5AA 1.395(19) . ?
C3AA H3AA 0.9500 . ?
C3AA C5AA 1.30(2) . ?
C3AA C4AA 1.429(17) . ?
C0AA H0AA 0.9500 . ?
C0AA C4AA 1.388(14) . ?
C5AA H5AA 0.9500 . ?
C4AA H4AA 0.9500 . ?
C2AB H2AB 0.9500 . ?
C2AB C1AB 1.349(14) . ?
C2AB C5AB 1.388(12) . ?
C1AB C0AB 1.398(14) . ?
C0AB H0AB 0.9500 . ?
C0AB C4AB 1.396(13) . ?
C4AB H4AB 0.9500 . ?
C4AB C3AB 1.384(18) . ?
C3AB H3AB 0.9500 . ?
C3AB C5AB 1.350(14) . ?
C5AB H5AB 0.9500 . ?

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
H1b N1 H1a 109.5 . . ?
H1c N1 H1a 109.5 . . ?
H1c N1 H1b 109.5 . . ?
C22 N1 H1a 109.5 . . ?
C22 N1 H1b 109.5 . . ?
C22 N1 H1c 109.5 . . ?
H2b N2 H2a 107.5 . . ?
C25 N2 H2a 108.47(14) . . ?
C25 N2 H2b 108.47(14) . . ?
C26 N2 H2a 108.47(14) . . ?
C26 N2 H2b 108.47(14) . . ?
C26 N2 C25 115.2(2) . . ?
C23 C22 N1 112.6(2) . . ?
C1AA C22 H22 110.7(7) . . ?
C1AB C22 H22a 105.5(6) . . ?
H23 C23 C22 107.38(17) . . ?
C24 C23 C22 115.7(3) . . ?
C24 C23 H23 107.38(16) . . ?
C34 C23 C22 110.2(3) . . ?
C34 C23 H23 107.38(18) . . ?
C34 C23 C24 108.5(3) . . ?
H24a C24 C23 108.87(17) . . ?
H24b C24 C23 108.87(17) . . ?
H24b C24 H24a 107.7 . . ?
C25 C24 C23 113.5(2) . . ?
C25 C24 H24a 108.87(16) . . ?
C25 C24 H24b 108.87(16) . . ?
C24 C25 N2 106.8(2) . . ?
H25 C25 N2 109.73(14) . . ?
H25 C25 C24 109.73(16) . . ?
C32 C25 N2 109.6(2) . . ?
C32 C25 C24 111.2(2) . . ?
C32 C25 H25 109.73(16) . . ?
H32a C32 C25 109.59(16) . . ?
H32b C32 C25 109.59(16) . . ?
H32b C32 H32a 108.1 . . ?
C33 C32 C25 110.3(2) . . ?
C33 C32 H32a 109.59(18) . . ?
C33 C32 H32b 109.59(17) . . ?
H33a C33 C32 109.27(17) . . ?
H33b C33 C32 109.27(18) . . ?
H33b C33 H33a 107.9 . . ?
C34 C33 C32 111.7(3) . . ?
C34 C33 H33a 109.27(18) . . ?
C34 C33 H33b 109.3(2) . . ?
C33 C34 C23 112.5(3) . . ?
H34a C34 C23 109.11(18) . . ?
H34a C34 C33 109.11(17) . . ?
H34b C34 C23 109.1(2) . . ?
H34b C34 C33 109.1(2) . . ?
H34b C34 H34a 107.8 . . ?
C28 C27 H27 120.73(18) . . ?
C26 C27 H27 120.73(17) . . ?
C26 C27 C28 118.5(3) . . ?
H28 C28 C27 119.73(18) . . ?
C29 C28 C27 120.5(3) . . ?
C29 C28 H28 119.7(2) . . ?
H29 C29 C28 119.7(2) . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7(2) . . ?
H30 C30 C29 120.1(2) . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.13(19) . . ?
H31 C31 C30 120.47(19) . . ?
C26 C31 C30 119.1(3) . . ?
C26 C31 H31 120.47(18) . . ?
C27 C26 N2 119.0(2) . . ?
C31 C26 N2 119.4(3) . . ?
C31 C26 C27 121.6(3) . . ?
O2 S1 O1 112.45(14) . . ?
O3 S1 O1 112.59(16) . . ?
O3 S1 O2 113.23(12) . . ?
C1 S1 O1 106.33(13) . . ?
C1 S1 O2 105.50(15) . . ?
C1 S1 O3 106.00(14) . . ?
O5 S2 O4 111.08(15) . . ?
O6 S2 O4 114.16(15) . . ?
O6 S2 O5 113.18(14) . . ?
C4 S2 O4 106.47(14) . . ?
C4 S2 O5 105.12(13) . . ?
C4 S2 O6 106.05(16) . . ?
C10 C1 S1 117.9(2) . . ?
C2 C1 S1 120.7(3) . . ?
C2 C1 C10 121.4(3) . . ?
H10 C10 C1 119.86(18) . . ?
C9 C10 C1 120.3(3) . . ?
C9 C10 H10 119.9(2) . . ?
H9 C9 C10 119.7(2) . . ?
C8 C9 C10 120.7(3) . . ?
C8 C9 H9 119.7(2) . . ?
H8 C8 C9 119.6(2) . . ?
C3 C8 C9 120.7(3) . . ?
C3 C8 H8 119.63(17) . . ?
C4 C3 C8 122.9(3) . . ?
C2 C3 C8 119.5(3) . . ?
C2 C3 C4 117.6(3) . . ?
C3 C4 S2 120.7(3) . . ?
C5 C4 S2 118.4(2) . . ?
C5 C4 C3 120.8(3) . . ?
H5 C5 C4 119.66(18) . . ?
C6 C5 C4 120.7(3) . . ?
C6 C5 H5 119.7(2) . . ?
H6 C6 C5 119.7(2) . . ?
C7 C6 C5 120.7(4) . . ?
C7 C6 H6 119.7(2) . . ?
H7 C7 C6 119.6(2) . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 H7 119.60(17) . . ?
C3 C2 C1 117.5(3) . . ?
C7 C2 C1 123.1(3) . . ?
C7 C2 C3 119.4(3) . . ?
C0AA C1AA C2AA 118.4(13) . . ?
H2AA C2AA C1AA 118.3(9) . . ?
C5AA C2AA C1AA 123.3(13) . . ?
C5AA C2AA H2AA 118.3(9) . . ?
C5AA C3AA H3AA 119.0(9) . . ?
C4AA C3AA H3AA 119.0(8) . . ?
C4AA C3AA C5AA 121.9(12) . . ?
H0AA C0AA C1AA 120.2(7) . . ?
C4AA C0AA C1AA 119.5(10) . . ?
C4AA C0AA H0AA 120.2(7) . . ?
C3AA C5AA C2AA 118.5(12) . . ?
H5AA C5AA C2AA 120.7(9) . . ?
H5AA C5AA C3AA 120.7(9) . . ?
C0AA C4AA C3AA 118.2(11) . . ?
H4AA C4AA C3AA 120.9(8) . . ?
H4AA C4AA C0AA 120.9(7) . . ?
C1AB C2AB H2AB 119.3(6) . . ?
C5AB C2AB H2AB 119.3(5) . . ?
C5AB C2AB C1AB 121.5(9) . . ?
C0AB C1AB C2AB 119.2(10) . . ?
H0AB C0AB C1AB 120.3(6) . . ?
C4AB C0AB C1AB 119.4(9) . . ?
C4AB C0AB H0AB 120.3(6) . . ?
H4AB C4AB C0AB 120.1(6) . . ?
C3AB C4AB C0AB 119.7(9) . . ?
C3AB C4AB H4AB 120.1(6) . . ?
H3AB C3AB C4AB 119.9(6) . . ?
C5AB C3AB C4AB 120.2(9) . . ?
C5AB C3AB H3AB 119.9(6) . . ?
C3AB C5AB C2AB 120.0(8) . . ?
H5AB C5AB C2AB 120.0(5) . . ?
H5AB C5AB C3AB 120.0(6) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 -0.911 -0.931 1105.4 424.5 ?


_olex2_date_sample_data_collection 2018-12-14
_olex2_date_sample_submission    2018-12-13
_olex2_exptl_crystal_mounting_method 
'The crystals were mounted on a loop using paratone oil.'
_olex2_submission_original_sample_id dm18o_0m
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
C22 C1AA 1 1
C22 C2AA 1 8
C22 C0AA 1 9
C22 C2AB 1 8
C22 C1AB 1 1
C22 C0AB 1 9
C1AA C2AA 1 2
C1AA C0AA 1 3
C1AA C5AA 1 10
C1AA C4AA 1 11
C2AA C3AA 1 12
C2AA C0AA 1 13
C2AA C5AA 1 4
C3AA C0AA 1 14
C3AA C5AA 1 5
C3AA C4AA 1 6
C0AA C4AA 1 7
C5AA C4AA 1 15
C2AB C0AB 1 13
C2AB C3AB 1 12
C2AB C5AB 1 4
C1AB C2AB 1 2
C1AB C0AB 1 3
C1AB C4AB 1 11
C1AB C5AB 1 10
C0AB C4AB 1 7
C3AB C0AB 1 14
C3AB C4AB 1 6
C3AB C5AB 1 5
C5AB C4AB 1 15

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.5351 0.0015 0.0015
2 0.0200 1.3459 0.0030 0.0030
3 0.0200 1.3998 0.0019 0.0019
4 0.0200 1.3915 0.0034 0.0034
5 0.0200 1.3249 0.0246 0.0246
6 0.0200 1.4069 0.0226 0.0226
7 0.0200 1.3916 0.0041 0.0041
8 0.0400 2.5064 0.0331 0.0331
9 0.0400 2.5403 0.0431 0.0431
10 0.0400 2.3989 0.0111 0.0111
11 0.0400 2.4107 0.0011 0.0011
12 0.0400 2.3442 0.0272 0.0272
13 0.0400 2.3632 0.0057 0.0057
14 0.0400 2.4108 0.0065 0.0065
15 0.0400 2.3787 0.0090 0.0090

####################################################################### 
# 
# 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_dm70n_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2gj4pv
_database_code_depnum_ccdc_archive 'CCDC 2279637'
loop_
_audit_author_name
_audit_author_address
'Evan P. Vanable'
;Department of Chemistry, University of Illinois at Urbana Champaign
United States of America
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2024-01-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
loop_
_audit_author_email
evanvanable@gmail.com
_chemical_name_common            ?
_chemical_name_systematic        
'4-(3-(ammonio(phenyl)methyl)cyclohexyl)morpholin-4-ium bis-(4-methylphenylsulfonate)'
_chemical_formula_moiety         '2(C7 H7 O3 S), C17 H28 N2 O'
_chemical_formula_sum            'C31 H42 N2 O7 S2'
_chemical_formula_weight         618.78
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.1123(4)
_cell_length_b                   11.2096(4)
_cell_length_c                   24.9678(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3110.10(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28796
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7011
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/4 (Bruker,2014/4) was used for absorption correction. wR2(int) was 0.0606 before and 0.0551 after correction. The Ratio of minimum to maximum transmission is 0.9402. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
_exptl_crystal_preparation       
'The free amine (0.54 mmol) was mixed with 2.1 equivalents of PTSA*H2O in 1.5 mL absolute ethanol. This was stirred for 5 minutes, then crystallizations were set up.'
_exptl_crystal_recrystallization_method 
'A layered crystallization was performed in a flame-sealed pipette. 0.5 mL of the aforementioned solution was placed into a pipette, another 0.3 mL ethanol layered onto it carefully, and 1.5 mL diethyl ether layered onto that. After 10 days large high quality crystals had formed.'
_exptl_crystal_size_max          0.529
_exptl_crystal_size_mid          0.475
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            77713
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.442
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                7454
_reflns_number_total             7735
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.290
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 3219 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         7735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.035
_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)+(0.0448P)²+0.6154P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0737
_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, All N(H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C27(H27), C29(H29),
 C30(H30), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C31(H31A,H31B,H31C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.64037(4) 0.38739(4) 0.46875(2) 0.01461(9) Uani 1 1 d . . . . .
O2 O 0.53586(12) 0.30943(11) 0.47542(5) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.74629(12) 0.33816(11) 0.49614(5) 0.0186(3) Uani 1 1 d . . . . .
O4 O 0.61612(13) 0.51039(11) 0.48329(6) 0.0226(3) Uani 1 1 d . . . . .
C18 C 0.67597(15) 0.38535(16) 0.39964(7) 0.0159(3) Uani 1 1 d . . . . .
C19 C 0.69099(17) 0.49126(17) 0.37161(8) 0.0209(4) Uani 1 1 d . . . . .
H19 H 0.6820 0.5658 0.3893 0.025 Uiso 1 1 calc R . . . .
C20 C 0.71917(19) 0.4870(2) 0.31761(9) 0.0275(4) Uani 1 1 d . . . . .
H20 H 0.7291 0.5593 0.2983 0.033 Uiso 1 1 calc R . . . .
C21 C 0.73311(19) 0.3789(2) 0.29124(8) 0.0284(4) Uani 1 1 d . . . . .
C22 C 0.71778(19) 0.2737(2) 0.32014(9) 0.0270(4) Uani 1 1 d . . . . .
H22 H 0.7273 0.1991 0.3026 0.032 Uiso 1 1 calc R . . . .
C23 C 0.68889(18) 0.27594(17) 0.37405(8) 0.0219(4) Uani 1 1 d . . . . .
H23 H 0.6780 0.2037 0.3933 0.026 Uiso 1 1 calc R . . . .
C24 C 0.7614(3) 0.3740(3) 0.23188(9) 0.0453(6) Uani 1 1 d . . . . .
H24A H 0.7460 0.4522 0.2157 0.068 Uiso 1 1 calc GR . . . .
H24B H 0.7102 0.3140 0.2147 0.068 Uiso 1 1 calc GR . . . .
H24C H 0.8461 0.3526 0.2268 0.068 Uiso 1 1 calc GR . . . .
S2 S 0.25319(4) 0.60426(3) 0.60166(2) 0.01352(9) Uani 1 1 d . . . . .
O5 O 0.13936(12) 0.53874(11) 0.60750(5) 0.0198(3) Uani 1 1 d . . . . .
O6 O 0.24755(13) 0.72339(10) 0.62378(5) 0.0197(3) Uani 1 1 d . . . . .
O7 O 0.29569(12) 0.60050(12) 0.54600(5) 0.0182(3) Uani 1 1 d . . . . .
C25 C 0.35970(16) 0.52339(15) 0.63960(7) 0.0144(3) Uani 1 1 d . . . . .
C26 C 0.45043(17) 0.45825(17) 0.61503(7) 0.0195(4) Uani 1 1 d . . . . .
H26 H 0.4614 0.4624 0.5773 0.023 Uiso 1 1 calc R . . . .
C27 C 0.52524(17) 0.38674(18) 0.64614(7) 0.0215(4) Uani 1 1 d . . . . .
H27 H 0.5877 0.3426 0.6293 0.026 Uiso 1 1 calc R . . . .
C28 C 0.51048(17) 0.37850(16) 0.70131(7) 0.0192(3) Uani 1 1 d . . . . .
C29 C 0.42235(18) 0.44926(17) 0.72544(8) 0.0205(4) Uani 1 1 d . . . . .
H29 H 0.4136 0.4480 0.7633 0.025 Uiso 1 1 calc R . . . .
C30 C 0.34752(17) 0.52129(16) 0.69507(7) 0.0181(3) Uani 1 1 d . . . . .
H30 H 0.2881 0.5691 0.7120 0.022 Uiso 1 1 calc R . . . .
C31 C 0.5846(2) 0.2918(2) 0.73379(8) 0.0264(4) Uani 1 1 d . . . . .
H31A H 0.5409 0.2163 0.7373 0.040 Uiso 1 1 calc GR . . . .
H31B H 0.5994 0.3253 0.7694 0.040 Uiso 1 1 calc GR . . . .
H31C H 0.6616 0.2777 0.7157 0.040 Uiso 1 1 calc GR . . . .
O1 O -0.17199(12) 0.77164(11) 0.59885(6) 0.0210(3) Uani 1 1 d . . . . .
N1 N 0.30505(13) 0.39520(13) 0.47885(6) 0.0132(3) Uani 1 1 d . . . . .
H1A H 0.3845 0.3811 0.4726 0.020 Uiso 1 1 calc GR . . . .
H1B H 0.2696 0.3275 0.4913 0.020 Uiso 1 1 calc GR . . . .
H1C H 0.2974 0.4542 0.5036 0.020 Uiso 1 1 calc GR . . . .
N2 N -0.01828(13) 0.63135(12) 0.53077(6) 0.0128(3) Uani 1 1 d . . . . .
H2 H 0.0242 0.5889 0.5605 0.019 Uiso 1 1 calc R . . . .
C1 C 0.24493(16) 0.43306(14) 0.42739(7) 0.0132(3) Uani 1 1 d . . . . .
H1 H 0.2535 0.5215 0.4237 0.016 Uiso 1 1 calc R . . . .
C2 C 0.10953(15) 0.40274(15) 0.43028(7) 0.0137(3) Uani 1 1 d . . . . .
H2A H 0.1023 0.3139 0.4314 0.016 Uiso 1 1 calc R . . . .
C3 C 0.04670(16) 0.45215(14) 0.48068(7) 0.0132(3) Uani 1 1 d . . . . .
H3A H -0.0349 0.4173 0.4835 0.016 Uiso 1 1 calc R . . . .
H3B H 0.0928 0.4282 0.5129 0.016 Uiso 1 1 calc R . . . .
C4 C 0.03702(15) 0.58789(14) 0.47881(7) 0.0129(3) Uani 1 1 d . . . . .
H4 H 0.1205 0.6209 0.4765 0.015 Uiso 1 1 calc R . . . .
C5 C -0.03180(17) 0.62986(16) 0.42967(7) 0.0192(4) Uani 1 1 d . . . . .
H5A H -0.0337 0.7181 0.4288 0.023 Uiso 1 1 calc R . . . .
H5B H -0.1157 0.6005 0.4313 0.023 Uiso 1 1 calc R . . . .
C6 C 0.02954(18) 0.58252(17) 0.37913(7) 0.0205(4) Uani 1 1 d . . . . .
H6A H 0.1104 0.6188 0.3758 0.025 Uiso 1 1 calc R . . . .
H6B H -0.0181 0.6060 0.3473 0.025 Uiso 1 1 calc R . . . .
C7 C 0.04177(17) 0.44614(17) 0.38055(7) 0.0190(4) Uani 1 1 d . . . . .
H7A H -0.0394 0.4099 0.3800 0.023 Uiso 1 1 calc R . . . .
H7B H 0.0851 0.4192 0.3481 0.023 Uiso 1 1 calc R . . . .
C8 C 0.30703(15) 0.37418(16) 0.38017(7) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.33672(17) 0.44155(18) 0.33514(8) 0.0213(4) Uani 1 1 d . . . . .
H9 H 0.3185 0.5243 0.3344 0.026 Uiso 1 1 calc R . . . .
C10 C 0.39250(17) 0.3891(2) 0.29141(8) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.4122 0.4359 0.2609 0.033 Uiso 1 1 calc R . . . .
C11 C 0.4196(2) 0.2685(2) 0.29214(9) 0.0315(5) Uani 1 1 d . . . . .
H11 H 0.4573 0.2324 0.2621 0.038 Uiso 1 1 calc R . . . .
C12 C 0.3915(2) 0.2009(2) 0.33668(9) 0.0290(5) Uani 1 1 d . . . . .
H12 H 0.4110 0.1184 0.3373 0.035 Uiso 1 1 calc R . . . .
C13 C 0.33487(18) 0.25260(17) 0.38046(8) 0.0209(4) Uani 1 1 d . . . . .
H13 H 0.3150 0.2052 0.4107 0.025 Uiso 1 1 calc R . . . .
C14 C 0.00144(16) 0.76280(14) 0.53937(7) 0.0152(3) Uani 1 1 d . . . . .
H14A H -0.0408 0.8088 0.5112 0.018 Uiso 1 1 calc R . . . .
H14B H 0.0884 0.7814 0.5371 0.018 Uiso 1 1 calc R . . . .
C15 C -0.04643(17) 0.79730(16) 0.59408(7) 0.0186(3) Uani 1 1 d . . . . .
H15A H -0.0017 0.7531 0.6220 0.022 Uiso 1 1 calc R . . . .
H15B H -0.0330 0.8836 0.6000 0.022 Uiso 1 1 calc R . . . .
C16 C -0.19163(18) 0.64680(16) 0.59159(8) 0.0218(4) Uani 1 1 d . . . . .
H16A H -0.2785 0.6292 0.5957 0.026 Uiso 1 1 calc R . . . .
H16B H -0.1475 0.6021 0.6196 0.026 Uiso 1 1 calc R . . . .
C17 C -0.15004(16) 0.60540(16) 0.53697(7) 0.0187(3) Uani 1 1 d . . . . .
H17A H -0.1645 0.5187 0.5331 0.022 Uiso 1 1 calc R . . . .
H17B H -0.1961 0.6473 0.5087 0.022 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O2 1.4629(13) . ?
S1 O3 1.4690(13) . ?
S1 O4 1.4510(13) . ?
S1 C18 1.7703(19) . ?
C18 C19 1.388(2) . ?
C18 C23 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 C22 1.393(3) . ?
C21 C24 1.516(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
S2 O5 1.4699(14) . ?
S2 O6 1.4465(12) . ?
S2 O7 1.4682(13) . ?
S2 C25 1.7664(18) . ?
C25 C26 1.388(2) . ?
C25 C30 1.392(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.392(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(3) . ?
C28 C29 1.397(3) . ?
C28 C31 1.510(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.385(3) . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O1 C15 1.430(2) . ?
O1 C16 1.428(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C1 1.509(2) . ?
N2 H2 1.0000 . ?
N2 C4 1.516(2) . ?
N2 C14 1.505(2) . ?
N2 C17 1.501(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.544(2) . ?
C1 C8 1.517(2) . ?
C2 H2A 1.0000 . ?
C2 C3 1.542(2) . ?
C2 C7 1.532(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.535(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.394(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(3) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.513(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 111.02(7) . . ?
O2 S1 C18 106.30(8) . . ?
O3 S1 C18 105.65(8) . . ?
O4 S1 O2 113.07(8) . . ?
O4 S1 O3 112.91(8) . . ?
O4 S1 C18 107.32(8) . . ?
C19 C18 S1 120.48(15) . . ?
C19 C18 C23 120.67(17) . . ?
C23 C18 S1 118.85(14) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.24(18) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.4 . . ?
C19 C20 C21 121.15(19) . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 118.66(19) . . ?
C20 C21 C24 121.2(2) . . ?
C22 C21 C24 120.1(2) . . ?
C21 C22 H22 119.4 . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
C18 C23 H23 120.4 . . ?
C22 C23 C18 119.15(18) . . ?
C22 C23 H23 120.4 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O5 S2 C25 105.48(8) . . ?
O6 S2 O5 112.71(8) . . ?
O6 S2 O7 113.69(8) . . ?
O6 S2 C25 107.33(8) . . ?
O7 S2 O5 110.88(8) . . ?
O7 S2 C25 106.10(8) . . ?
C26 C25 S2 121.31(14) . . ?
C26 C25 C30 120.11(17) . . ?
C30 C25 S2 118.51(14) . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.36(17) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.3 . . ?
C28 C27 C26 121.38(17) . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C29 118.18(17) . . ?
C27 C28 C31 120.69(17) . . ?
C29 C28 C31 121.08(18) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 C28 121.05(18) . . ?
C30 C29 H29 119.5 . . ?
C25 C30 H30 120.1 . . ?
C29 C30 C25 119.76(17) . . ?
C29 C30 H30 120.1 . . ?
C28 C31 H31A 109.5 . . ?
C28 C31 H31B 109.5 . . ?
C28 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C16 O1 C15 109.62(14) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C4 N2 H2 106.9 . . ?
C14 N2 H2 106.9 . . ?
C14 N2 C4 112.19(13) . . ?
C17 N2 H2 106.9 . . ?
C17 N2 C4 114.93(13) . . ?
C17 N2 C14 108.49(13) . . ?
N1 C1 H1 108.4 . . ?
N1 C1 C2 109.24(13) . . ?
N1 C1 C8 109.75(14) . . ?
C2 C1 H1 108.4 . . ?
C8 C1 H1 108.4 . . ?
C8 C1 C2 112.57(14) . . ?
C1 C2 H2A 107.4 . . ?
C3 C2 C1 113.60(14) . . ?
C3 C2 H2A 107.4 . . ?
C7 C2 C1 111.79(14) . . ?
C7 C2 H2A 107.4 . . ?
C7 C2 C3 108.96(14) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.42(14) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
N2 C4 C3 108.84(13) . . ?
N2 C4 H4 107.8 . . ?
N2 C4 C5 112.78(14) . . ?
C3 C4 H4 107.8 . . ?
C5 C4 C3 111.63(14) . . ?
C5 C4 H4 107.8 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
C4 C5 C6 109.53(15) . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.47(16) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C2 C7 C6 112.24(14) . . ?
C2 C7 H7A 109.2 . . ?
C2 C7 H7B 109.2 . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C1 119.92(16) . . ?
C9 C8 C13 118.69(17) . . ?
C13 C8 C1 121.39(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(2) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.79(19) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.5(2) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 119.9 . . ?
C12 C13 C8 120.21(19) . . ?
C12 C13 H13 119.9 . . ?
N2 C14 H14A 109.9 . . ?
N2 C14 H14B 109.9 . . ?
N2 C14 C15 109.09(14) . . ?
H14A C14 H14B 108.3 . . ?
C15 C14 H14A 109.9 . . ?
C15 C14 H14B 109.9 . . ?
O1 C15 C14 111.48(15) . . ?
O1 C15 H15A 109.3 . . ?
O1 C15 H15B 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
O1 C16 H16A 109.3 . . ?
O1 C16 H16B 109.3 . . ?
O1 C16 C17 111.61(15) . . ?
H16A C16 H16B 108.0 . . ?
C17 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
N2 C17 C16 109.36(15) . . ?
N2 C17 H17A 109.8 . . ?
N2 C17 H17B 109.8 . . ?
C16 C17 H17A 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?

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
N1 H1A O2 0.91 1.87 2.7405(19) 160.6 .
N1 H1B O3 0.91 1.90 2.7675(19) 158.4 4_456
N1 H1C O7 0.91 1.95 2.8492(19) 168.6 .
N2 H2 O5 1.00 1.83 2.7958(19) 162.7 .

_olex2_exptl_crystal_mounting_method 
'Paratone oil was used for mounting on a thin metal loop. '
_olex2_submission_original_sample_id ev-e-1357-cy-morph
_olex2_submission_special_instructions 'No special instructions were received'
