# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1479247'
_audit_update_record             
;
2016-05-11 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H25 Cl2 N7 O S'
_chemical_formula_weight         590.52

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'
Cl Cl 0.1484 0.1585 '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                   8.7640(5)
_cell_length_b                   10.6660(5)
_cell_length_c                   15.4487(9)
_cell_angle_alpha                74.316(5)
_cell_angle_beta                 82.742(5)
_cell_angle_gamma                82.883(4)
_cell_volume                     1373.09(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4826
_cell_measurement_theta_min      2.951
_cell_measurement_theta_max      25.005

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_F_000             612
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    0.351
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.992
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.  
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8289
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.951
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4826
_reflns_number_gt                3391
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0440P)²+0.2233P] 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         4826
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
S S 0.39809(8) 0.16323(6) 0.03002(5) 0.0648(2) Uani 1 1 d . . . . .
Cl2 Cl 0.30962(10) 0.43368(9) 0.54664(6) 0.0922(3) Uani 1 1 d . . . . .
Cl1 Cl 0.42015(11) 0.60146(7) 0.18698(6) 0.0959(3) Uani 1 1 d . . . . .
N5 N 0.2313(2) 0.52545(17) -0.04562(13) 0.0479(5) Uani 1 1 d . . . . .
N3 N -0.0245(2) 0.73382(17) -0.32724(13) 0.0444(5) Uani 1 1 d . . . . .
N4 N 0.1927(2) 0.33830(16) -0.06946(12) 0.0420(5) Uani 1 1 d . . . . .
N7 N 0.4953(2) 0.32213(19) 0.19174(14) 0.0550(5) Uani 1 1 d . . . . .
H7 H 0.5007 0.3899 0.1465 0.066 Uiso 1 1 calc R U . . .
N1 N 0.1236(2) 0.90542(19) -0.34877(14) 0.0561(5) Uani 1 1 d . . . . .
N6 N 0.3270(2) 0.42633(19) 0.00672(14) 0.0509(5) Uani 1 1 d . . . . .
O1 O 0.5220(3) 0.10050(19) 0.22799(14) 0.0912(7) Uani 1 1 d . . . . .
C14 C 0.1534(3) 0.4715(2) -0.09008(15) 0.0407(5) Uani 1 1 d . . . . .
C12 C 0.1080(3) 0.5225(2) -0.25300(15) 0.0466(6) Uani 1 1 d . . . . .
H12A H 0.2096 0.5538 -0.2699 0.056 Uiso 1 1 calc R U . . .
H12B H 0.1183 0.4300 -0.2503 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1237(3) 0.2402(2) -0.09552(15) 0.0444(6) Uani 1 1 d . . . . .
C13 C 0.0469(3) 0.54160(19) -0.15959(15) 0.0411(5) Uani 1 1 d . . . . .
H13 H -0.0530 0.5049 -0.1421 0.049 Uiso 1 1 calc R U . . .
C11 C 0.0203(3) 0.6877(2) -0.16586(15) 0.0445(6) Uani 1 1 d . . . . .
H11A H -0.0270 0.7010 -0.1084 0.053 Uiso 1 1 calc R U . . .
H11B H 0.1185 0.7253 -0.1793 0.053 Uiso 1 1 calc R U . . .
C17 C -0.0299(3) 0.2231(2) -0.06825(17) 0.0527(6) Uani 1 1 d . . . . .
H17 H -0.0880 0.2751 -0.0341 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2214(3) 0.9041(2) -0.52410(18) 0.0579(7) Uani 1 1 d . . . . .
C9 C 0.0019(3) 0.5948(2) -0.32426(16) 0.0481(6) Uani 1 1 d . . . . .
H9A H 0.0475 0.5848 -0.3829 0.058 Uiso 1 1 calc R U . . .
H9B H -0.0962 0.5570 -0.3112 0.058 Uiso 1 1 calc R U . . .
C10 C -0.0838(3) 0.7549(2) -0.23931(16) 0.0488(6) Uani 1 1 d . . . . .
H10A H -0.1850 0.7228 -0.2223 0.059 Uiso 1 1 calc R U . . .
H10B H -0.0961 0.8481 -0.2441 0.059 Uiso 1 1 calc R U . . .
C28 C 0.4546(3) 0.2479(3) 0.35696(18) 0.0620(7) Uani 1 1 d . . . . .
H28 H 0.4825 0.1616 0.3549 0.074 Uiso 1 1 calc R U . . .
C3 C 0.0316(3) 0.7582(2) -0.52513(18) 0.0600(7) Uani 1 1 d . . . . .
H3 H -0.0496 0.7093 -0.4959 0.072 Uiso 1 1 calc R U . . .
C19 C 0.1388(5) 0.0691(3) -0.16947(19) 0.0768(10) Uani 1 1 d . . . . .
H19 H 0.1950 0.0166 -0.2038 0.092 Uiso 1 1 calc R U . . .
C5 C 0.1070(3) 0.8231(2) -0.47721(16) 0.0476(6) Uani 1 1 d . . . . .
C26 C 0.3701(3) 0.4011(3) 0.44289(19) 0.0597(7) Uani 1 1 d . . . . .
N2 N 0.2832(3) 0.9855(2) -0.48567(18) 0.0686(7) Uani 1 1 d . . . . .
C23 C 0.4575(3) 0.3465(2) 0.27723(17) 0.0489(6) Uani 1 1 d . . . . .
C22 C 0.5240(3) 0.2055(3) 0.17236(18) 0.0539(6) Uani 1 1 d . . . . .
C15 C 0.3022(3) 0.3175(2) -0.01072(16) 0.0463(6) Uani 1 1 d . . . . .
C25 C 0.3753(3) 0.5022(3) 0.3658(2) 0.0630(7) Uani 1 1 d . . . . .
H25 H 0.3504 0.5883 0.3689 0.076 Uiso 1 1 calc R U . . .
C18 C 0.2103(3) 0.1644(2) -0.14682(17) 0.0617(7) Uani 1 1 d . . . . .
H18 H 0.3137 0.1764 -0.1659 0.074 Uiso 1 1 calc R U . . .
C8 C 0.0715(3) 0.8204(2) -0.38342(16) 0.0446(6) Uani 1 1 d . . . . .
C24 C 0.4181(3) 0.4735(2) 0.28415(18) 0.0552(7) Uani 1 1 d . . . . .
C21 C 0.5579(3) 0.2099(3) 0.07344(17) 0.0577(7) Uani 1 1 d . . . . .
H21A H 0.6492 0.1514 0.0651 0.069 Uiso 1 1 calc R U . . .
H21B H 0.5793 0.2978 0.0397 0.069 Uiso 1 1 calc R U . . .
C20 C -0.0135(5) 0.0527(3) -0.1414(2) 0.0792(9) Uani 1 1 d . . . . .
H20 H -0.0600 -0.0112 -0.1565 0.095 Uiso 1 1 calc R U . . .
C035 C -0.0966(4) 0.1284(2) -0.0920(2) 0.0686(8) Uani 1 1 d . . . . .
H035 H -0.2002 0.1166 -0.0736 0.082 Uiso 1 1 calc R U . . .
C27 C 0.4114(3) 0.2756(3) 0.43883(19) 0.0676(8) Uani 1 1 d . . . . .
H27 H 0.4103 0.2082 0.4917 0.081 Uiso 1 1 calc R U . . .
C1 C 0.0767(4) 0.7664(3) -0.6143(2) 0.0744(8) Uani 1 1 d . . . . .
H1 H 0.0257 0.7240 -0.6457 0.089 Uiso 1 1 calc R U . . .
C2 C 0.1987(4) 0.8383(3) -0.6578(2) 0.0819(10) Uani 1 1 d . . . . .
H2 H 0.2325 0.8395 -0.7175 0.098 Uiso 1 1 calc R U . . .
C7 C 0.2246(3) 0.9842(3) -0.4041(2) 0.0687(8) Uani 1 1 d . . . . .
H7A H 0.2569 1.0465 -0.3801 0.082 Uiso 1 1 calc R U . . .
C4 C 0.2694(4) 0.9064(3) -0.6153(2) 0.0744(9) Uani 1 1 d . . . . .
H4 H 0.3499 0.9551 -0.6460 0.089 Uiso 1 1 calc R U . . .


_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
S C15 1.744(2) . ?
S C21 1.803(3) . ?
Cl2 C26 1.736(3) . ?
Cl1 C24 1.735(3) . ?
N5 C14 1.303(3) . ?
N5 N6 1.401(3) . ?
N3 C8 1.374(3) . ?
N3 C10 1.458(3) . ?
N3 C9 1.461(3) . ?
N4 C15 1.361(3) . ?
N4 C14 1.378(3) . ?
N4 C16 1.438(3) . ?
N7 C22 1.344(3) . ?
N7 C23 1.405(3) . ?
N7 H7 0.8600 . ?
N1 C8 1.320(3) . ?
N1 C7 1.351(3) . ?
N6 C15 1.309(3) . ?
O1 C22 1.214(3) . ?
C14 C13 1.493(3) . ?
C12 C9 1.514(3) . ?
C12 C13 1.532(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C16 C17 1.377(3) . ?
C16 C18 1.378(3) . ?
C13 C11 1.525(3) . ?
C13 H13 0.9800 . ?
C11 C10 1.514(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C17 C035 1.378(3) . ?
C17 H17 0.9300 . ?
C6 N2 1.370(3) . ?
C6 C5 1.404(3) . ?
C6 C4 1.412(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C28 C27 1.372(4) . ?
C28 C23 1.387(3) . ?
C28 H28 0.9300 . ?
C3 C1 1.366(4) . ?
C3 C5 1.406(3) . ?
C3 H3 0.9300 . ?
C19 C20 1.368(4) . ?
C19 C18 1.398(4) . ?
C19 H19 0.9300 . ?
C5 C8 1.436(3) . ?
C26 C27 1.359(4) . ?
C26 C25 1.374(4) . ?
N2 C7 1.296(4) . ?
C23 C24 1.385(3) . ?
C22 C21 1.508(3) . ?
C25 C24 1.374(4) . ?
C25 H25 0.9300 . ?
C18 H18 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C20 C035 1.346(4) . ?
C20 H20 0.9300 . ?
C035 H035 0.9300 . ?
C27 H27 0.9300 . ?
C1 C2 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C4 1.347(4) . ?
C2 H2 0.9300 . ?
C7 H7A 0.9300 . ?
C4 H4 0.9300 . ?

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
C15 S C21 99.41(12) . . ?
C14 N5 N6 107.90(18) . . ?
C8 N3 C10 118.53(19) . . ?
C8 N3 C9 120.01(18) . . ?
C10 N3 C9 111.90(17) . . ?
C15 N4 C14 104.38(18) . . ?
C15 N4 C16 126.80(18) . . ?
C14 N4 C16 128.53(19) . . ?
C22 N7 C23 127.7(2) . . ?
C22 N7 H7 116.2 . . ?
C23 N7 H7 116.2 . . ?
C8 N1 C7 115.9(2) . . ?
C15 N6 N5 106.07(19) . . ?
N5 C14 N4 110.1(2) . . ?
N5 C14 C13 126.20(19) . . ?
N4 C14 C13 123.5(2) . . ?
C9 C12 C13 111.86(18) . . ?
C9 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
C9 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C17 C16 C18 120.7(2) . . ?
C17 C16 N4 119.0(2) . . ?
C18 C16 N4 120.4(2) . . ?
C14 C13 C11 112.09(19) . . ?
C14 C13 C12 111.42(17) . . ?
C11 C13 C12 108.96(17) . . ?
C14 C13 H13 108.1 . . ?
C11 C13 H13 108.1 . . ?
C12 C13 H13 108.1 . . ?
C10 C11 C13 110.04(19) . . ?
C10 C11 H11A 109.7 . . ?
C13 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
C13 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C16 C17 C035 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C035 C17 H17 120.3 . . ?
N2 C6 C5 122.2(2) . . ?
N2 C6 C4 118.8(3) . . ?
C5 C6 C4 119.0(3) . . ?
N3 C9 C12 111.28(19) . . ?
N3 C9 H9A 109.4 . . ?
C12 C9 H9A 109.4 . . ?
N3 C9 H9B 109.4 . . ?
C12 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
N3 C10 C11 113.07(18) . . ?
N3 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N3 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C27 C28 C23 121.0(3) . . ?
C27 C28 H28 119.5 . . ?
C23 C28 H28 119.5 . . ?
C1 C3 C5 120.5(3) . . ?
C1 C3 H3 119.8 . . ?
C5 C3 H3 119.8 . . ?
C20 C19 C18 120.3(3) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C6 C5 C3 118.8(2) . . ?
C6 C5 C8 115.5(2) . . ?
C3 C5 C8 125.6(2) . . ?
C27 C26 C25 120.7(3) . . ?
C27 C26 Cl2 119.6(2) . . ?
C25 C26 Cl2 119.7(2) . . ?
C7 N2 C6 114.7(2) . . ?
C24 C23 C28 117.2(2) . . ?
C24 C23 N7 119.9(2) . . ?
C28 C23 N7 122.9(2) . . ?
O1 C22 N7 124.7(3) . . ?
O1 C22 C21 119.6(2) . . ?
N7 C22 C21 115.7(2) . . ?
N6 C15 N4 111.5(2) . . ?
N6 C15 S 126.51(19) . . ?
N4 C15 S 121.90(17) . . ?
C24 C25 C26 118.6(3) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
C16 C18 C19 118.3(3) . . ?
C16 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
N1 C8 N3 117.3(2) . . ?
N1 C8 C5 121.3(2) . . ?
N3 C8 C5 121.4(2) . . ?
C25 C24 C23 122.2(2) . . ?
C25 C24 Cl1 118.3(2) . . ?
C23 C24 Cl1 119.5(2) . . ?
C22 C21 S 111.60(17) . . ?
C22 C21 H21A 109.3 . . ?
S C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
S C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C035 C20 C19 120.5(3) . . ?
C035 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C035 C17 120.7(3) . . ?
C20 C035 H035 119.6 . . ?
C17 C035 H035 119.6 . . ?
C26 C27 C28 120.2(3) . . ?
C26 C27 H27 119.9 . . ?
C28 C27 H27 119.9 . . ?
C3 C1 C2 119.8(3) . . ?
C3 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C4 C2 C1 121.4(3) . . ?
C4 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
N2 C7 N1 129.5(3) . . ?
N2 C7 H7A 115.3 . . ?
N1 C7 H7A 115.3 . . ?
C2 C4 C6 120.1(3) . . ?
C2 C4 H4 119.9 . . ?
C6 C4 H4 119.9 . . ?

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.037

