# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c2_a
_database_code_depnum_ccdc_archive 'CCDC 1969285'
loop_
_audit_author_name
_audit_author_address
'Wen Yang'
;Hunan University
China
;
_audit_update_record             
;
2019-12-02 deposited with the CCDC.	2020-01-19 downloaded from the CCDC.
;
_audit_creation_date             2019-04-28
_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         '4(C22 H24 N2 S)'
_chemical_formula_sum            'C88 H96 N8 S4'
_chemical_formula_weight         1393.96
_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'
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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   48.132(3)
_cell_length_b                   6.9037(4)
_cell_length_c                   10.8793(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.383(4)
_cell_angle_gamma                90
_cell_volume                     3608.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4055
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1191 before and 0.0516 after correction. The Ratio of minimum to maximum transmission is 0.8410. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       64
_diffrn_reflns_limit_h_min       -55
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18608
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.445
_diffrn_reflns_theta_min         2.543
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3103
_reflns_number_total             4544
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.355
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0863
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+2.4711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1251
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00C(H00E), C00G(H00J), C00J(H00N), C00K(H00O)
2.b Secondary CH2 refined with riding coordinates:
 C005(H00A,H00B), C00B(H00C,H00D), C00E(H00G,H00H), C00H(H00K,H00L), C00L(H00P,
 H00Q), C00M(H00R,H00S), C00O(H00U,H00V)
2.c Aromatic/amide H refined with riding coordinates:
 C006(H006), C00D(H00F), C00F(H00I), C00I(H00M), C00N(H00T), C00P(H00W)
;
_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
S001 S 0.36944(2) 0.11511(8) 0.32951(5) 0.02990(15) Uani 1 1 d . . . . .
N002 N 0.36617(3) 0.4246(2) 0.46549(14) 0.0227(3) Uani 1 1 d . . . . .
N003 N 0.24292(4) -0.1773(3) 0.66286(15) 0.0328(4) Uani 1 1 d . . . . .
C004 C 0.27957(4) 0.0460(3) 0.57077(16) 0.0218(4) Uani 1 1 d . . . . .
C005 C 0.41638(4) 0.2670(3) 0.62108(15) 0.0224(4) Uani 1 1 d . . . . .
H00A H 0.4080 0.3864 0.6531 0.027 Uiso 1 1 calc R . . . .
H00B H 0.4064 0.1545 0.6534 0.027 Uiso 1 1 calc R . . . .
C006 C 0.29404(4) 0.2336(3) 0.40108(16) 0.0228(4) Uani 1 1 d . . . . .
H006 H 0.2910 0.2783 0.3188 0.027 Uiso 1 1 calc R . . . .
C007 C 0.38252(4) 0.2797(3) 0.42950(16) 0.0211(4) Uani 1 1 d . . . . .
C008 C 0.31769(4) 0.2924(3) 0.47055(16) 0.0211(4) Uani 1 1 d . . . . .
C009 C 0.41327(4) 0.2669(2) 0.47840(15) 0.0193(4) Uani 1 1 d . . . . .
C00A C 0.25934(4) -0.0793(3) 0.62249(17) 0.0255(4) Uani 1 1 d . . . . .
C00B C 0.43024(4) 0.4350(3) 0.42529(15) 0.0211(4) Uani 1 1 d . . . . .
H00C H 0.4290 0.4277 0.3342 0.025 Uiso 1 1 calc R . . . .
H00D H 0.4223 0.5605 0.4496 0.025 Uiso 1 1 calc R . . . .
C00C C 0.46084(4) 0.4237(3) 0.47299(16) 0.0243(4) Uani 1 1 d . . . . .
H00E H 0.4712 0.5360 0.4402 0.029 Uiso 1 1 calc R . . . .
C00D C 0.27496(4) 0.1110(3) 0.45035(16) 0.0240(4) Uani 1 1 d . . . . .
H00F H 0.2588 0.0715 0.4024 0.029 Uiso 1 1 calc R . . . .
C00E C 0.42683(4) 0.0777(3) 0.43538(17) 0.0236(4) Uani 1 1 d . . . . .
H00G H 0.4167 -0.0347 0.4675 0.028 Uiso 1 1 calc R . . . .
H00H H 0.4252 0.0714 0.3443 0.028 Uiso 1 1 calc R . . . .
C00F C 0.32210(4) 0.2275(3) 0.59090(17) 0.0263(4) Uani 1 1 d . . . . .
H00I H 0.3382 0.2677 0.6387 0.032 Uiso 1 1 calc R . . . .
C00G C 0.44735(4) 0.2565(3) 0.66508(16) 0.0258(4) Uani 1 1 d . . . . .
H00J H 0.4490 0.2602 0.7571 0.031 Uiso 1 1 calc R . . . .
C00H C 0.47360(4) 0.2353(3) 0.42928(17) 0.0266(4) Uani 1 1 d . . . . .
H00K H 0.4725 0.2308 0.3382 0.032 Uiso 1 1 calc R . . . .
H00L H 0.4934 0.2280 0.4588 0.032 Uiso 1 1 calc R . . . .
C00I C 0.30316(4) 0.1046(3) 0.64174(17) 0.0252(4) Uani 1 1 d . . . . .
H00M H 0.3062 0.0606 0.7242 0.030 Uiso 1 1 calc R . . . .
C00J C 0.33681(4) 0.4388(3) 0.41542(17) 0.0243(4) Uani 1 1 d . . . . .
H00N H 0.3360 0.4249 0.3238 0.029 Uiso 1 1 calc R . . . .
C00K C 0.45763(4) 0.0652(3) 0.47989(17) 0.0265(4) Uani 1 1 d . . . . .
H00O H 0.4656 -0.0587 0.4500 0.032 Uiso 1 1 calc R . . . .
C00L C 0.37267(4) 0.5932(3) 0.5475(2) 0.0330(5) Uani 1 1 d . . . . .
H00P H 0.3903 0.6561 0.5271 0.040 Uiso 1 1 calc R . . . .
H00Q H 0.3740 0.5536 0.6352 0.040 Uiso 1 1 calc R . . . .
C00M C 0.46025(4) 0.0689(3) 0.62075(17) 0.0305(5) Uani 1 1 d . . . . .
H00R H 0.4505 -0.0440 0.6542 0.037 Uiso 1 1 calc R . . . .
H00S H 0.4801 0.0621 0.6499 0.037 Uiso 1 1 calc R . . . .
C00N C 0.32892(4) 0.6411(3) 0.44974(19) 0.0303(5) Uani 1 1 d . . . . .
H00T H 0.3119 0.7017 0.4232 0.036 Uiso 1 1 calc R . . . .
C00O C 0.46269(4) 0.4309(3) 0.61449(16) 0.0275(4) Uani 1 1 d . . . . .
H00U H 0.4824 0.4285 0.6455 0.033 Uiso 1 1 calc R . . . .
H00V H 0.4542 0.5525 0.6428 0.033 Uiso 1 1 calc R . . . .
C00P C 0.34838(4) 0.7243(3) 0.5208(2) 0.0326(5) Uani 1 1 d . . . . .
H00W H 0.3472 0.8526 0.5517 0.039 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
S001 C007 1.6702(18) . ?
N002 C007 1.346(2) . ?
N002 C00J 1.487(2) . ?
N002 C00L 1.488(2) . ?
N003 C00A 1.147(2) . ?
C004 C00A 1.441(3) . ?
C004 C00D 1.390(2) . ?
C004 C00I 1.395(2) . ?
C005 C009 1.551(2) . ?
C005 C00G 1.540(3) . ?
C006 C008 1.389(2) . ?
C006 C00D 1.380(3) . ?
C007 C009 1.545(2) . ?
C008 C00F 1.388(3) . ?
C008 C00J 1.514(2) . ?
C009 C00B 1.550(2) . ?
C009 C00E 1.546(2) . ?
C00B C00C 1.534(2) . ?
C00C C00H 1.526(3) . ?
C00C C00O 1.538(2) . ?
C00E C00K 1.534(3) . ?
C00F C00I 1.384(3) . ?
C00G C00M 1.527(3) . ?
C00G C00O 1.532(3) . ?
C00H C00K 1.524(3) . ?
C00J C00N 1.500(3) . ?
C00K C00M 1.530(3) . ?
C00L C00P 1.493(3) . ?
C00N C00P 1.311(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
C007 N002 C00J 120.12(14) . . ?
C007 N002 C00L 130.53(15) . . ?
C00J N002 C00L 109.26(14) . . ?
C00D C004 C00A 119.19(16) . . ?
C00D C004 C00I 120.47(17) . . ?
C00I C004 C00A 120.32(16) . . ?
C00G C005 C009 110.21(14) . . ?
C00D C006 C008 120.69(16) . . ?
N002 C007 S001 119.39(13) . . ?
N002 C007 C009 120.45(15) . . ?
C009 C007 S001 120.16(13) . . ?
C006 C008 C00J 118.49(16) . . ?
C00F C008 C006 119.57(16) . . ?
C00F C008 C00J 121.76(16) . . ?
C007 C009 C005 112.23(14) . . ?
C007 C009 C00B 110.14(14) . . ?
C007 C009 C00E 110.90(14) . . ?
C00B C009 C005 110.56(14) . . ?
C00E C009 C005 106.61(14) . . ?
C00E C009 C00B 106.18(14) . . ?
N003 C00A C004 179.0(2) . . ?
C00C C00B C009 110.63(14) . . ?
C00B C00C C00O 109.56(14) . . ?
C00H C00C C00B 109.50(15) . . ?
C00H C00C C00O 109.81(15) . . ?
C006 C00D C004 119.43(17) . . ?
C00K C00E C009 111.67(14) . . ?
C00I C00F C008 120.47(17) . . ?
C00M C00G C005 110.24(15) . . ?
C00M C00G C00O 109.85(15) . . ?
C00O C00G C005 109.25(15) . . ?
C00K C00H C00C 108.85(14) . . ?
C00F C00I C004 119.37(16) . . ?
N002 C00J C008 113.42(14) . . ?
N002 C00J C00N 102.65(15) . . ?
C00N C00J C008 110.74(15) . . ?
C00H C00K C00E 109.95(15) . . ?
C00H C00K C00M 109.59(16) . . ?
C00M C00K C00E 109.65(15) . . ?
N002 C00L C00P 102.86(16) . . ?
C00G C00M C00K 108.62(15) . . ?
C00P C00N C00J 111.83(18) . . ?
C00G C00O C00C 109.49(15) . . ?
C00N C00P C00L 111.91(18) . . ?

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
S001 C007 C009 C005 -126.17(14) . . . . ?
S001 C007 C009 C00B 110.18(15) . . . . ?
S001 C007 C009 C00E -7.06(19) . . . . ?
N002 C007 C009 C005 54.8(2) . . . . ?
N002 C007 C009 C00B -68.83(19) . . . . ?
N002 C007 C009 C00E 173.94(15) . . . . ?
N002 C00J C00N C00P -7.1(2) . . . . ?
N002 C00L C00P C00N 7.6(2) . . . . ?
C005 C009 C00B C00C 55.51(18) . . . . ?
C005 C009 C00E C00K -59.22(18) . . . . ?
C005 C00G C00M C00K 60.2(2) . . . . ?
C005 C00G C00O C00C -62.02(19) . . . . ?
C006 C008 C00F C00I 0.2(3) . . . . ?
C006 C008 C00J N002 -153.33(16) . . . . ?
C006 C008 C00J C00N 91.9(2) . . . . ?
C007 N002 C00J C008 75.3(2) . . . . ?
C007 N002 C00J C00N -165.14(15) . . . . ?
C007 N002 C00L C00P 164.53(18) . . . . ?
C007 C009 C00B C00C -179.88(14) . . . . ?
C007 C009 C00E C00K 178.33(14) . . . . ?
C008 C006 C00D C004 -0.1(3) . . . . ?
C008 C00F C00I C004 0.2(3) . . . . ?
C008 C00J C00N C00P 114.24(19) . . . . ?
C009 C005 C00G C00M -61.59(19) . . . . ?
C009 C005 C00G C00O 59.21(19) . . . . ?
C009 C00B C00C C00H 62.41(18) . . . . ?
C009 C00B C00C C00O -58.08(19) . . . . ?
C009 C00E C00K C00H -59.98(19) . . . . ?
C009 C00E C00K C00M 60.6(2) . . . . ?
C00A C004 C00D C006 178.92(17) . . . . ?
C00A C004 C00I C00F -178.95(17) . . . . ?
C00B C009 C00E C00K 58.69(18) . . . . ?
C00B C00C C00H C00K -60.37(18) . . . . ?
C00B C00C C00O C00G 61.50(19) . . . . ?
C00C C00H C00K C00E 58.95(18) . . . . ?
C00C C00H C00K C00M -61.64(19) . . . . ?
C00D C004 C00I C00F -0.4(3) . . . . ?
C00D C006 C008 C00F -0.2(3) . . . . ?
C00D C006 C008 C00J -175.44(16) . . . . ?
C00E C009 C00B C00C -59.75(17) . . . . ?
C00E C00K C00M C00G -59.1(2) . . . . ?
C00F C008 C00J N002 31.6(2) . . . . ?
C00F C008 C00J C00N -83.2(2) . . . . ?
C00G C005 C009 C007 -179.35(14) . . . . ?
C00G C005 C009 C00B -55.95(19) . . . . ?
C00G C005 C009 C00E 59.04(18) . . . . ?
C00H C00C C00O C00G -58.80(19) . . . . ?
C00H C00K C00M C00G 61.7(2) . . . . ?
C00I C004 C00D C006 0.4(3) . . . . ?
C00J N002 C007 S001 -0.6(2) . . . . ?
C00J N002 C007 C009 178.37(15) . . . . ?
C00J N002 C00L C00P -11.9(2) . . . . ?
C00J C008 C00F C00I 175.22(17) . . . . ?
C00J C00N C00P C00L -0.3(3) . . . . ?
C00L N002 C007 S001 -176.80(16) . . . . ?
C00L N002 C007 C009 2.2(3) . . . . ?
C00L N002 C00J C008 -107.77(17) . . . . ?
C00L N002 C00J C00N 11.76(19) . . . . ?
C00M C00G C00O C00C 59.03(19) . . . . ?
C00O C00C C00H C00K 59.98(19) . . . . ?
C00O C00G C00M C00K -60.3(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
