# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ns_327_0m
_database_code_depnum_ccdc_archive 'CCDC 1859342'
_audit_update_record             
;
2018-07-31 deposited with the CCDC.
2018-11-14 downloaded from the CCDC.
;
_audit_creation_date             2018-07-20
_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        'Diazo compound'
_chemical_formula_moiety         'C24 H26 N6 O3 S'
_chemical_formula_sum            'C24 H26 N6 O3 S'
_chemical_formula_weight         478.57
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1010(4)
_cell_length_b                   9.2238(4)
_cell_length_c                   14.9779(7)
_cell_angle_alpha                80.357(2)
_cell_angle_beta                 89.219(2)
_cell_angle_gamma                82.426(2)
_cell_volume                     1228.71(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6589
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.285
_cell_measurement_theta_min      2.259
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Reddish brown'
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       2
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36352
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.285
_diffrn_reflns_theta_min         2.259
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  Bruker
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4433
_reflns_number_total             5996
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.359
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         5996
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.0887
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0836P)²+1.1893P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1992
_refine_ls_wR_factor_ref         0.2139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C3(H3A,H3B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C11(H11), C10(H10), C18(H18), C9(H9), C15(H15), C16(H16),
 C21(H21), C23(H23), N3(H3), C24(H24), C20(H20)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
C7 C 0.0442(3) 0.3533(3) 0.61213(19) 0.0533(7) Uani 1 1 d . . . . .
H7 H -0.0514 0.3980 0.5958 0.064 Uiso 1 1 calc R . . . .
C6 C 0.1274(3) 0.2731(3) 0.55411(17) 0.0422(5) Uani 1 1 d . . . . .
C12 C 0.0454(3) 0.2246(3) 0.23582(18) 0.0481(6) Uani 1 1 d . . . . .
H12A H 0.1220 0.2884 0.2212 0.058 Uiso 1 1 calc R . . . .
H12B H -0.0459 0.2763 0.2069 0.058 Uiso 1 1 calc R . . . .
C8 C 0.1042(4) 0.3664(4) 0.6946(2) 0.0716(9) Uani 1 1 d . . . . .
H8 H 0.0491 0.4210 0.7333 0.086 Uiso 1 1 calc R . . . .
C5 C 0.1116(3) 0.2507(3) 0.39157(18) 0.0426(5) Uani 1 1 d . . . . .
C11 C 0.2696(3) 0.2060(3) 0.5792(2) 0.0512(6) Uani 1 1 d . . . . .
H11 H 0.3258 0.1524 0.5404 0.061 Uiso 1 1 calc R . . . .
C10 C 0.3273(4) 0.2190(4) 0.6616(2) 0.0654(8) Uani 1 1 d . . . . .
H10 H 0.4225 0.1734 0.6785 0.078 Uiso 1 1 calc R . . . .
C13 C 0.0879(3) 0.0841(3) 0.19759(18) 0.0509(6) Uani 1 1 d . . . . .
C18 C -0.0181(4) 0.0284(4) 0.15162(19) 0.0595(7) Uani 1 1 d . . . . .
H18 H -0.1133 0.0800 0.1450 0.071 Uiso 1 1 calc R . . . .
C9 C 0.2450(4) 0.2990(4) 0.7191(2) 0.0744(10) Uani 1 1 d . . . . .
H9 H 0.2847 0.3074 0.7746 0.089 Uiso 1 1 calc R . . . .
C17 C 0.0121(5) -0.1000(4) 0.1155(2) 0.0716(9) Uani 1 1 d . . . . .
O1 O 0.3437(2) 0.0505(3) 0.24724(18) 0.0744(7) Uani 1 1 d . . . . .
H1 H 0.3122 0.1207 0.2724 0.112 Uiso 1 1 calc GR . . . .
C15 C 0.2617(5) -0.1233(4) 0.1676(3) 0.0859(12) Uani 1 1 d . . . . .
H15 H 0.3569 -0.1750 0.1721 0.103 Uiso 1 1 calc R . . . .
C16 C 0.1521(6) -0.1743(4) 0.1234(3) 0.0902(13) Uani 1 1 d . . . . .
H16 H 0.1741 -0.2605 0.0986 0.108 Uiso 1 1 calc R . . . .
C14 C 0.2302(4) 0.0064(4) 0.2058(2) 0.0609(7) Uani 1 1 d . . . . .
C3 C -0.2446(3) 0.2125(3) 0.3809(2) 0.0505(6) Uani 1 1 d . . . . .
H3A H -0.2568 0.3000 0.3343 0.061 Uiso 1 1 calc R . . . .
H3B H -0.3268 0.1573 0.3758 0.061 Uiso 1 1 calc R . . . .
C4 C -0.0996(3) 0.1165(3) 0.36578(18) 0.0452(6) Uani 1 1 d . . . . .
H4A H -0.0704 0.0511 0.4222 0.054 Uiso 1 1 calc R . . . .
H4B H -0.1172 0.0548 0.3216 0.054 Uiso 1 1 calc R . . . .
C22 C -0.4615(4) -0.3494(4) -0.0864(2) 0.0685(8) Uani 1 1 d . . . . .
C21 C -0.3251(6) -0.4257(5) -0.0921(3) 0.0936(12) Uani 1 1 d . . . . .
H21 H -0.3108 -0.5000 -0.1274 0.112 Uiso 1 1 calc R . . . .
C23 C -0.4947(5) -0.2355(4) -0.0383(3) 0.0792(10) Uani 1 1 d . . . . .
H23 H -0.5905 -0.1864 -0.0366 0.095 Uiso 1 1 calc R . . . .
N6 N -0.5798(6) -0.3929(4) -0.1374(3) 0.0965(11) Uani 1 1 d . . . . .
N1 N -0.2473(2) 0.2580(2) 0.46994(16) 0.0469(5) Uani 1 1 d . . . . .
C2 C -0.2835(4) 0.1398(4) 0.5413(2) 0.0667(8) Uani 1 1 d . . . . .
H2A H -0.3809 0.1168 0.5305 0.100 Uiso 1 1 calc GR . . . .
H2B H -0.2808 0.1718 0.5989 0.100 Uiso 1 1 calc GR . . . .
H2C H -0.2125 0.0530 0.5412 0.100 Uiso 1 1 calc GR . . . .
O3 O -0.7018(5) -0.3284(5) -0.1347(3) 0.1503(18) Uani 1 1 d . . . . .
N2 N 0.0247(2) 0.1988(2) 0.33441(14) 0.0438(5) Uani 1 1 d . . . . .
S1 S 0.27538(8) 0.31009(10) 0.35872(5) 0.0606(2) Uani 1 1 d . . . . .
C1 C -0.3520(3) 0.3922(3) 0.4722(3) 0.0708(9) Uani 1 1 d . . . . .
H1A H -0.3286 0.4696 0.4249 0.106 Uiso 1 1 calc GR . . . .
H1B H -0.3450 0.4234 0.5298 0.106 Uiso 1 1 calc GR . . . .
H1C H -0.4510 0.3717 0.4632 0.106 Uiso 1 1 calc GR . . . .
O2 O -0.5500(6) -0.4925(5) -0.1796(3) 0.1580(18) Uani 1 1 d . . . . .
N3 N 0.0556(2) 0.2525(2) 0.47482(14) 0.0441(5) Uani 1 1 d . . . . .
H3 H -0.0361 0.2393 0.4808 0.053 Uiso 1 1 calc R . . . .
C24 C -0.3778(6) -0.1970(5) 0.0077(3) 0.0942(13) Uani 1 1 d . . . . .
H24 H -0.3918 -0.1209 0.0419 0.113 Uiso 1 1 calc R . . . .
N5 N -0.0991(5) -0.2510(5) 0.0450(3) 0.1067(13) Uani 1 1 d . . . . .
C19 C -0.2327(5) -0.2813(6) 0.0000(3) 0.0972(16) Uani 1 1 d . . . . .
N4 N -0.1315(4) -0.1357(3) 0.07051(17) 0.0794(10) Uani 1 1 d . . . . .
C20 C -0.2154(6) -0.3957(6) -0.0488(3) 0.0998(14) Uani 1 1 d . . . . .
H20 H -0.1231 -0.4520 -0.0505 0.120 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
C7 C6 1.387(4) . ?
C7 C8 1.387(4) . ?
C6 C11 1.386(4) . ?
C6 N3 1.416(3) . ?
C12 C13 1.506(4) . ?
C12 N2 1.470(3) . ?
C8 C9 1.374(5) . ?
C5 N2 1.358(3) . ?
C5 S1 1.694(3) . ?
C5 N3 1.342(3) . ?
C11 C10 1.377(4) . ?
C10 C9 1.378(5) . ?
C13 C18 1.391(4) . ?
C13 C14 1.391(4) . ?
C18 C17 1.377(4) . ?
C17 C16 1.362(6) . ?
C17 N4 1.575(5) . ?
O1 C14 1.353(4) . ?
C15 C16 1.378(6) . ?
C15 C14 1.406(5) . ?
C3 C4 1.526(3) . ?
C3 N1 1.463(4) . ?
C4 N2 1.472(3) . ?
C22 C21 1.353(6) . ?
C22 C23 1.370(5) . ?
C22 N6 1.464(5) . ?
C21 C20 1.282(7) . ?
C23 C24 1.391(5) . ?
N6 O3 1.192(5) . ?
N6 O2 1.201(5) . ?
N1 C2 1.461(4) . ?
N1 C1 1.464(3) . ?
C24 C19 1.455(7) . ?
N5 C19 1.479(6) . ?
N5 N4 1.189(5) . ?
C19 C20 1.372(7) . ?

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
C8 C7 C6 119.7(3) . . ?
C7 C6 N3 117.0(2) . . ?
C11 C6 C7 119.8(2) . . ?
C11 C6 N3 122.9(2) . . ?
N2 C12 C13 113.4(2) . . ?
C9 C8 C7 120.1(3) . . ?
N2 C5 S1 122.1(2) . . ?
N3 C5 N2 114.4(2) . . ?
N3 C5 S1 123.53(18) . . ?
C10 C11 C6 119.9(3) . . ?
C11 C10 C9 120.4(3) . . ?
C18 C13 C12 119.4(3) . . ?
C14 C13 C12 122.8(3) . . ?
C14 C13 C18 117.9(3) . . ?
C17 C18 C13 122.7(3) . . ?
C8 C9 C10 120.1(3) . . ?
C18 C17 N4 110.5(3) . . ?
C16 C17 C18 118.8(4) . . ?
C16 C17 N4 130.7(3) . . ?
C16 C15 C14 120.3(4) . . ?
C17 C16 C15 120.9(3) . . ?
C13 C14 C15 119.4(3) . . ?
O1 C14 C13 123.6(3) . . ?
O1 C14 C15 117.0(3) . . ?
N1 C3 C4 111.5(2) . . ?
N2 C4 C3 115.2(2) . . ?
C21 C22 C23 125.0(4) . . ?
C21 C22 N6 116.1(4) . . ?
C23 C22 N6 118.9(4) . . ?
C20 C21 C22 120.2(5) . . ?
C22 C23 C24 116.6(4) . . ?
O3 N6 C22 118.6(4) . . ?
O3 N6 O2 122.8(5) . . ?
O2 N6 C22 118.6(5) . . ?
C3 N1 C1 111.7(2) . . ?
C2 N1 C3 111.6(2) . . ?
C2 N1 C1 109.6(2) . . ?
C12 N2 C4 114.9(2) . . ?
C5 N2 C12 122.2(2) . . ?
C5 N2 C4 122.9(2) . . ?
C5 N3 C6 128.6(2) . . ?
C23 C24 C19 116.8(4) . . ?
N4 N5 C19 106.4(4) . . ?
C24 C19 N5 122.3(5) . . ?
C20 C19 C24 120.6(4) . . ?
C20 C19 N5 117.1(5) . . ?
N5 N4 C17 106.7(4) . . ?
C21 C20 C19 120.7(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol: acetonitrile'
