# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_EPMO2
_database_code_depnum_ccdc_archive 'CCDC 1887556'
loop_
_audit_author_name
_audit_author_address
'Jingyun Tan'
;University of Macau
China
;
_audit_update_record             
;
2019-04-08 deposited with the CCDC.	2019-05-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 N5 O2 S, 0.5(C H2 Cl2)'
_chemical_formula_sum            'C29.50 H22 Cl N5 O2 S'
_chemical_formula_weight         546.03

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0089(2)
_cell_length_b                   12.1459(4)
_cell_length_c                   13.9061(4)
_cell_angle_alpha                82.255(3)
_cell_angle_beta                 80.785(2)
_cell_angle_gamma                79.244(3)
_cell_volume                     1304.11(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    12115
_cell_measurement_theta_min      4.6460
_cell_measurement_theta_max      73.4760

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             566
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.354
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81137
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            21033
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.726
_diffrn_reflns_theta_max         73.779
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5161
_reflns_number_gt                4916
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1020P)²+1.9283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5161
_refine_ls_number_parameters     373
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1679
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cl2 Cl 0.5381(6) 0.0208(4) 0.9939(4) 0.1065(12) Uani 0.5 1 d . . P B .
S1 S 0.31585(7) 1.00380(5) 0.75827(4) 0.02085(17) Uani 1 1 d . . . . .
O1 O 0.4961(2) 0.67163(13) 0.95763(11) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.5171(2) 0.29139(13) 0.68955(12) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.2623(2) 1.04524(15) 0.54332(13) 0.0161(4) Uani 1 1 d . . . . .
N2 N 0.2478(2) 0.63447(16) 1.04019(13) 0.0184(4) Uani 1 1 d . . . . .
H2A H 0.266625 0.674943 1.082249 0.022 Uiso 1 1 calc R U . . .
H2B H 0.156339 0.604728 1.050046 0.022 Uiso 1 1 calc R U . . .
N3 N 0.1038(3) 0.44322(17) 0.90300(14) 0.0219(4) Uani 1 1 d . . . . .
N4 N 0.5457(2) 0.42177(15) 0.79182(13) 0.0154(4) Uani 1 1 d . . . . .
N5 N 0.2753(3) 0.47025(18) 0.50352(15) 0.0234(4) Uani 1 1 d . . . . .
C1 C 0.1880(3) 1.12171(19) 0.70239(17) 0.0187(4) Uani 1 1 d . . . . .
C2 C 0.1101(3) 1.2085(2) 0.75898(18) 0.0234(5) Uani 1 1 d . . . . .
H2 H 0.118194 1.200239 0.825631 0.028 Uiso 1 1 calc R U . . .
C3 C 0.0205(3) 1.3072(2) 0.71639(19) 0.0248(5) Uani 1 1 d . . . . .
H3 H -0.028850 1.366051 0.753708 0.030 Uiso 1 1 calc R U . . .
C4 C 0.0057(3) 1.3170(2) 0.61770(19) 0.0235(5) Uani 1 1 d . . . . .
H4 H -0.056276 1.382213 0.588967 0.028 Uiso 1 1 calc R U . . .
C5 C 0.0824(3) 1.23014(19) 0.56091(17) 0.0205(5) Uani 1 1 d . . . . .
H5 H 0.070265 1.237880 0.494824 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1776(3) 1.13146(19) 0.60195(17) 0.0177(4) Uani 1 1 d . . . . .
C7 C 0.2879(3) 1.07160(19) 0.43599(16) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.389920 1.022394 0.409504 0.021 Uiso 1 1 calc R U . . .
H7AB H 0.309781 1.148386 0.420878 0.021 Uiso 1 1 calc R U . . .
C8 C 0.1396(3) 1.0600(2) 0.38341(17) 0.0203(5) Uani 1 1 d . . . . .
H8A H 0.173921 1.069806 0.313846 0.030 Uiso 1 1 calc R U . . .
H8B H 0.042358 1.116396 0.401160 0.030 Uiso 1 1 calc R U . . .
H8C H 0.109332 0.986498 0.402194 0.030 Uiso 1 1 calc R U . . .
C9 C 0.2916(3) 0.93221(18) 0.58199(16) 0.0152(4) Uani 1 1 d . . . . .
C10 C 0.3179(3) 0.84414(19) 0.52269(15) 0.0164(4) Uani 1 1 d . . . . .
H10 H 0.313328 0.861290 0.455839 0.020 Uiso 1 1 calc R U . . .
C11 C 0.3503(3) 0.73278(19) 0.56104(16) 0.0163(4) Uani 1 1 d . . . . .
H11 H 0.368780 0.676743 0.519223 0.020 Uiso 1 1 calc R U . . .
C12 C 0.3562(3) 0.70169(18) 0.66172(15) 0.0153(4) Uani 1 1 d . . . . .
C13 C 0.3309(3) 0.78961(19) 0.72128(15) 0.0155(4) Uani 1 1 d . . . . .
H13 H 0.332816 0.772193 0.788348 0.019 Uiso 1 1 calc R U . . .
C14 C 0.3033(3) 0.90134(19) 0.68270(15) 0.0156(4) Uani 1 1 d . . . . .
C15 C 0.4035(3) 0.58423(18) 0.69957(15) 0.0151(4) Uani 1 1 d . . . . .
C16 C 0.4018(3) 0.48946(19) 0.65816(15) 0.0162(4) Uani 1 1 d . . . . .
C17 C 0.3312(3) 0.47872(19) 0.57298(16) 0.0179(4) Uani 1 1 d . . . . .
C18 C 0.4936(3) 0.39435(18) 0.71728(16) 0.0165(4) Uani 1 1 d . . . . .
C19 C 0.6008(3) 0.2042(2) 0.75557(18) 0.0249(5) Uani 1 1 d . . . . .
H19A H 0.599094 0.131750 0.735829 0.037 Uiso 1 1 calc R U . . .
H19B H 0.541573 0.208984 0.820977 0.037 Uiso 1 1 calc R U . . .
H19C H 0.717539 0.214012 0.753800 0.037 Uiso 1 1 calc R U . . .
C20 C 0.4828(3) 0.54446(18) 0.79469(15) 0.0146(4) Uani 1 1 d . . . . .
C21 C 0.3481(3) 0.55881(18) 0.88469(15) 0.0150(4) Uani 1 1 d . . . . .
C22 C 0.2121(3) 0.49574(18) 0.89550(15) 0.0163(4) Uani 1 1 d . . . . .
C23 C 0.3615(3) 0.61769(18) 0.95902(16) 0.0154(4) Uani 1 1 d . . . . .
C24 C 0.6307(3) 0.66130(18) 0.88112(15) 0.0157(4) Uani 1 1 d . . . . .
C25 C 0.7664(3) 0.71484(19) 0.88875(17) 0.0192(5) Uani 1 1 d . . . . .
H25 H 0.764245 0.752798 0.942840 0.023 Uiso 1 1 calc R U . . .
C26 C 0.9045(3) 0.71086(19) 0.81486(17) 0.0204(5) Uani 1 1 d . . . . .
H26 H 0.996146 0.746154 0.819184 0.025 Uiso 1 1 calc R U . . .
C27 C 0.9066(3) 0.65399(19) 0.73378(17) 0.0201(5) Uani 1 1 d . . . . .
H27 H 0.999646 0.651425 0.684163 0.024 Uiso 1 1 calc R U . . .
C28 C 0.7702(3) 0.60138(18) 0.72715(16) 0.0174(4) Uani 1 1 d . . . . .
H28 H 0.771915 0.563981 0.672794 0.021 Uiso 1 1 calc R U . . .
C29 C 0.6298(3) 0.60408(17) 0.80170(15) 0.0149(4) Uani 1 1 d . . . . .
C30 C 0.7425(12) 0.0628(6) 0.9810(5) 0.058(2) Uani 0.5 1 d . . P . .
H30A H 0.731569 0.143507 0.962947 0.070 Uiso 0.5 1 calc R U P A 1
H30B H 0.788581 0.044935 1.042741 0.070 Uiso 0.5 1 calc R U P A 1
Cl1A Cl 0.8759(2) -0.00633(16) 0.89324(14) 0.0335(7) Uani 0.347(3) 1 d . . P B
1
Cl1B Cl 0.9332(7) -0.0410(5) 0.9631(4) 0.0484(18) Uani 0.153(3) 1 d . . P B 2


_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
Cl2 Cl2 0.847(6) 2_657 ?
Cl2 C30 1.779(10) . ?
S1 C14 1.759(2) . ?
S1 C1 1.764(2) . ?
O1 C23 1.358(3) . ?
O1 C24 1.389(3) . ?
O2 C18 1.329(3) . ?
O2 C19 1.443(3) . ?
N1 C9 1.397(3) . ?
N1 C6 1.418(3) . ?
N1 C7 1.473(3) . ?
N2 C23 1.345(3) . ?
N3 C22 1.154(3) . ?
N4 C18 1.282(3) . ?
N4 C20 1.485(3) . ?
N5 C17 1.152(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.400(3) . ?
C2 C3 1.388(4) . ?
C3 C4 1.384(4) . ?
C4 C5 1.393(3) . ?
C5 C6 1.399(3) . ?
C7 C8 1.528(3) . ?
C9 C10 1.402(3) . ?
C9 C14 1.414(3) . ?
C10 C11 1.378(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.404(3) . ?
C12 C15 1.455(3) . ?
C13 C14 1.381(3) . ?
C15 C16 1.358(3) . ?
C15 C20 1.539(3) . ?
C16 C17 1.422(3) . ?
C16 C18 1.474(3) . ?
C20 C29 1.514(3) . ?
C20 C21 1.522(3) . ?
C21 C23 1.362(3) . ?
C21 C22 1.422(3) . ?
C24 C29 1.384(3) . ?
C24 C25 1.391(3) . ?
C25 C26 1.382(3) . ?
C26 C27 1.396(3) . ?
C27 C28 1.385(3) . ?
C28 C29 1.401(3) . ?
C30 Cl1A 1.691(8) . ?
C30 Cl1B 1.797(10) . ?
Cl1B Cl1B 2.052(10) 2_757 ?

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
Cl2 Cl2 C30 159.9(9) 2_657 . ?
C14 S1 C1 100.02(10) . . ?
C23 O1 C24 119.42(17) . . ?
C18 O2 C19 114.28(17) . . ?
C9 N1 C6 121.74(18) . . ?
C9 N1 C7 118.19(18) . . ?
C6 N1 C7 118.86(18) . . ?
C18 N4 C20 106.54(17) . . ?
C2 C1 C6 121.2(2) . . ?
C2 C1 S1 118.14(18) . . ?
C6 C1 S1 120.49(17) . . ?
C3 C2 C1 120.3(2) . . ?
C4 C3 C2 119.1(2) . . ?
C3 C4 C5 120.7(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C1 117.7(2) . . ?
C5 C6 N1 120.9(2) . . ?
C1 C6 N1 121.3(2) . . ?
N1 C7 C8 115.89(18) . . ?
N1 C9 C10 121.94(19) . . ?
N1 C9 C14 121.24(19) . . ?
C10 C9 C14 116.77(19) . . ?
C11 C10 C9 121.6(2) . . ?
C10 C11 C12 121.7(2) . . ?
C13 C12 C11 116.8(2) . . ?
C13 C12 C15 122.09(19) . . ?
C11 C12 C15 120.80(19) . . ?
C14 C13 C12 121.6(2) . . ?
C13 C14 C9 121.4(2) . . ?
C13 C14 S1 117.80(16) . . ?
C9 C14 S1 120.16(17) . . ?
C16 C15 C12 129.2(2) . . ?
C16 C15 C20 106.08(18) . . ?
C12 C15 C20 124.49(19) . . ?
C15 C16 C17 128.8(2) . . ?
C15 C16 C18 106.97(19) . . ?
C17 C16 C18 124.2(2) . . ?
N5 C17 C16 179.4(2) . . ?
N4 C18 O2 126.4(2) . . ?
N4 C18 C16 114.47(19) . . ?
O2 C18 C16 119.17(19) . . ?
N4 C20 C29 110.12(17) . . ?
N4 C20 C21 107.52(16) . . ?
C29 C20 C21 109.93(17) . . ?
N4 C20 C15 105.33(17) . . ?
C29 C20 C15 112.43(17) . . ?
C21 C20 C15 111.32(17) . . ?
C23 C21 C22 119.04(19) . . ?
C23 C21 C20 123.67(19) . . ?
C22 C21 C20 116.87(18) . . ?
N3 C22 C21 178.7(2) . . ?
N2 C23 O1 110.62(18) . . ?
N2 C23 C21 127.0(2) . . ?
O1 C23 C21 122.32(19) . . ?
C29 C24 O1 122.90(19) . . ?
C29 C24 C25 121.9(2) . . ?
O1 C24 C25 115.15(19) . . ?
C26 C25 C24 119.1(2) . . ?
C25 C26 C27 120.1(2) . . ?
C28 C27 C26 120.1(2) . . ?
C27 C28 C29 120.5(2) . . ?
C24 C29 C28 118.3(2) . . ?
C24 C29 C20 121.62(19) . . ?
C28 C29 C20 120.11(19) . . ?
Cl1A C30 Cl2 108.8(5) . . ?
Cl2 C30 Cl1B 119.4(5) . . ?
C30 Cl1B Cl1B 92.4(5) . 2_757 ?

_refine_diff_density_max         1.319
_refine_diff_density_min         -1.592
_refine_diff_density_rms         0.095


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2, toluene'
