# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_03KK038B2
_audit_block_doi                 10.5517/ccdc.csd.cc2cmzbb
_database_code_depnum_ccdc_archive 'CCDC 2193942'
loop_
_audit_author_name
_audit_author_address
'Nozomi Saito'
;Meiji Pharmaceutical University
Japan
;
_audit_update_record             
;
2022-08-01 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C20 H15 N O4 S'
_chemical_formula_moiety         'C20 H15 N O4 S'
_chemical_formula_weight         365.40
_chemical_melting_point          369-373

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   15.1494(16)
_cell_length_b                   15.0265(16)
_cell_length_c                   7.6701(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.096(7)
_cell_angle_gamma                90.0000
_cell_volume                     1713.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7000
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760.00
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_T_max  0.927

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            19514
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_av_R_equivalents  0.1198
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.973
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3100
_reflns_number_gt                2029
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0773
_refine_ls_wR_factor_ref         0.2292
_refine_ls_wR_factor_gt          0.2045
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3100
_refine_ls_number_parameters     235
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1105P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.17115(7) 0.57817(7) 0.74037(13) 0.0566(4) Uani 1 1 d . . . . .
O1 O 0.12818(17) 0.49498(18) 0.7030(3) 0.0672(8) Uani 1 1 d . . . . .
O2 O 0.41209(19) 0.56251(18) 0.8206(4) 0.0769(9) Uani 1 1 d . . . . .
O3 O 0.21387(19) 0.60126(18) 0.9148(3) 0.0653(8) Uani 1 1 d . . . . .
O4 O 0.31074(15) 0.65470(16) 0.6556(3) 0.0524(7) Uani 1 1 d . . . . .
N6 N 0.2576(2) 0.5737(2) 0.6270(4) 0.0512(8) Uani 1 1 d . . . . .
C1 C 0.2302(3) 0.5306(3) 0.3027(6) 0.0668(12) Uani 1 1 d . . . . .
H1 H 0.223010 0.513232 0.181686 0.080 Uiso 1 1 calc R U . . .
C2 C 0.2392(3) 0.5521(3) 0.4533(6) 0.0555(10) Uani 1 1 d . . . . .
C3 C 0.0974(2) 0.6626(2) 0.6491(5) 0.0481(9) Uani 1 1 d . . . . .
C4 C 0.1200(3) 0.7515(3) 0.6894(5) 0.0528(10) Uani 1 1 d . . . . .
H4 H 0.175406 0.766240 0.765095 0.063 Uiso 1 1 calc R U . . .
C5 C 0.0605(3) 0.8177(3) 0.6172(5) 0.0525(10) Uani 1 1 d . . . . .
H5 H 0.076083 0.878099 0.643263 0.063 Uiso 1 1 calc R U . . .
C6 C -0.0212(3) 0.7981(3) 0.5077(5) 0.0515(10) Uani 1 1 d . . . . .
C7 C -0.0422(3) 0.7093(3) 0.4724(5) 0.0548(10) Uani 1 1 d . . . . .
H7 H -0.098386 0.694242 0.399764 0.066 Uiso 1 1 calc R U . . .
C8 C 0.0172(3) 0.6417(3) 0.5409(5) 0.0536(10) Uani 1 1 d . . . . .
H8 H 0.002123 0.581325 0.512908 0.064 Uiso 1 1 calc R U . . .
C9 C -0.0831(3) 0.8716(3) 0.4328(5) 0.0655(12) Uani 1 1 d . . . . .
H9A H -0.137427 0.846505 0.359032 0.079 Uiso 1 1 calc R U . . .
H9B H -0.099734 0.906103 0.530087 0.079 Uiso 1 1 calc R U . . .
H9C H -0.052918 0.910557 0.360204 0.079 Uiso 1 1 calc R U . . .
C10 C 0.3938(3) 0.6366(3) 0.7685(5) 0.0540(10) Uani 1 1 d . . . . .
C12 C 0.4049(3) 0.8007(3) 0.7588(5) 0.0576(11) Uani 1 1 d . . . . .
H12 H 0.344310 0.801981 0.696316 0.069 Uiso 1 1 calc R U . . .
C13 C 0.4518(3) 0.8803(3) 0.8002(6) 0.0675(12) Uani 1 1 d . . . . .
H13 H 0.423130 0.935444 0.765210 0.081 Uiso 1 1 calc R U . . .
C14 C 0.5378(3) 0.8793(3) 0.8897(6) 0.0672(12) Uani 1 1 d . . . . .
H14 H 0.568309 0.934153 0.918360 0.081 Uiso 1 1 calc R U . . .
C15 C 0.5832(3) 0.7992(3) 0.9417(5) 0.0555(10) Uani 1 1 d . . . . .
C16 C 0.6738(3) 0.7994(3) 1.0319(5) 0.0626(11) Uani 1 1 d . . . . .
H16 H 0.704087 0.854504 1.059210 0.075 Uiso 1 1 calc R U . . .
C17 C 0.7181(3) 0.7222(3) 1.0800(5) 0.0651(12) Uani 1 1 d . . . . .
H17 H 0.779235 0.723259 1.139042 0.078 Uiso 1 1 calc R U . . .
C18 C 0.6731(3) 0.6408(3) 1.0423(5) 0.0639(11) Uani 1 1 d . . . . .
H18 H 0.704175 0.587011 1.078780 0.077 Uiso 1 1 calc R U . . .
C19 C 0.5864(3) 0.6372(3) 0.9551(5) 0.0552(10) Uani 1 1 d . . . . .
H19 H 0.557919 0.581078 0.929748 0.066 Uiso 1 1 calc R U . . .
C20 C 0.5379(2) 0.7165(2) 0.9014(5) 0.0488(9) Uani 1 1 d . . . . .
C21 C 0.4460(2) 0.7199(2) 0.8081(5) 0.0508(10) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O1 1.413(3) . ?
S1 O3 1.413(3) . ?
S1 N6 1.706(3) . ?
S1 C3 1.746(4) . ?
O2 C10 1.197(4) . ?
O4 C10 1.410(4) . ?
O4 N6 1.452(3) . ?
N6 C2 1.347(5) . ?
C1 C2 1.182(5) . ?
C1 H1 0.9500 . ?
C3 C8 1.369(5) . ?
C3 C4 1.399(5) . ?
C4 C5 1.384(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.387(5) . ?
C6 C9 1.491(5) . ?
C7 C8 1.391(5) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C21 1.481(5) . ?
C12 C21 1.383(5) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.350(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.405(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.413(5) . ?
C15 C20 1.425(5) . ?
C16 C17 1.355(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.403(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.356(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.419(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.438(5) . ?

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
O1 S1 O3 121.22(17) . . ?
O1 S1 N6 103.35(16) . . ?
O3 S1 N6 103.63(17) . . ?
O1 S1 C3 109.09(17) . . ?
O3 S1 C3 110.05(17) . . ?
N6 S1 C3 108.57(16) . . ?
C10 O4 N6 109.6(3) . . ?
C2 N6 O4 110.7(3) . . ?
C2 N6 S1 118.8(3) . . ?
O4 N6 S1 110.4(2) . . ?
C2 C1 H1 180.0 . . ?
C1 C2 N6 174.6(4) . . ?
C8 C3 C4 120.3(4) . . ?
C8 C3 S1 120.1(3) . . ?
C4 C3 S1 119.6(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.8(4) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C7 117.8(4) . . ?
C5 C6 C9 119.9(4) . . ?
C7 C6 C9 122.3(4) . . ?
C6 C7 C8 121.4(4) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C3 C8 C7 119.7(4) . . ?
C3 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C10 O4 120.4(4) . . ?
O2 C10 C21 129.6(4) . . ?
O4 C10 C21 109.9(3) . . ?
C21 C12 C13 120.4(4) . . ?
C21 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C14 C13 C12 120.3(4) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 121.7(4) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 120.9(4) . . ?
C14 C15 C20 119.8(4) . . ?
C16 C15 C20 119.3(4) . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C19 C18 C17 121.5(4) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 118.0(4) . . ?
C19 C20 C21 124.9(3) . . ?
C15 C20 C21 117.1(3) . . ?
C12 C21 C20 120.6(4) . . ?
C12 C21 C10 119.4(4) . . ?
C20 C21 C10 119.9(3) . . ?

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
C10 O4 N6 C2 -119.3(3) . . . . ?
C10 O4 N6 S1 107.1(2) . . . . ?
O1 S1 N6 C2 52.1(3) . . . . ?
O3 S1 N6 C2 179.4(3) . . . . ?
C3 S1 N6 C2 -63.6(3) . . . . ?
O1 S1 N6 O4 -178.52(19) . . . . ?
O3 S1 N6 O4 -51.2(2) . . . . ?
C3 S1 N6 O4 65.7(2) . . . . ?
O1 S1 C3 C8 -7.8(4) . . . . ?
O3 S1 C3 C8 -143.0(3) . . . . ?
N6 S1 C3 C8 104.2(3) . . . . ?
O1 S1 C3 C4 171.2(3) . . . . ?
O3 S1 C3 C4 35.9(3) . . . . ?
N6 S1 C3 C4 -76.9(3) . . . . ?
C8 C3 C4 C5 -0.5(5) . . . . ?
S1 C3 C4 C5 -179.5(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
C4 C5 C6 C9 -179.9(3) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C9 C6 C7 C8 178.8(3) . . . . ?
C4 C3 C8 C7 -0.5(5) . . . . ?
S1 C3 C8 C7 178.4(3) . . . . ?
C6 C7 C8 C3 1.5(6) . . . . ?
N6 O4 C10 O2 2.2(4) . . . . ?
N6 O4 C10 C21 -176.2(3) . . . . ?
C21 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 C16 178.6(4) . . . . ?
C13 C14 C15 C20 -0.7(6) . . . . ?
C14 C15 C16 C17 -179.1(4) . . . . ?
C20 C15 C16 C17 0.2(6) . . . . ?
C15 C16 C17 C18 -1.0(6) . . . . ?
C16 C17 C18 C19 1.4(6) . . . . ?
C17 C18 C19 C20 -1.0(6) . . . . ?
C18 C19 C20 C15 0.2(6) . . . . ?
C18 C19 C20 C21 179.8(4) . . . . ?
C14 C15 C20 C19 179.6(3) . . . . ?
C16 C15 C20 C19 0.2(5) . . . . ?
C14 C15 C20 C21 -0.2(5) . . . . ?
C16 C15 C20 C21 -179.5(3) . . . . ?
C13 C12 C21 C20 -0.5(6) . . . . ?
C13 C12 C21 C10 177.8(4) . . . . ?
C19 C20 C21 C12 -178.9(3) . . . . ?
C15 C20 C21 C12 0.8(5) . . . . ?
C19 C20 C21 C10 2.8(6) . . . . ?
C15 C20 C21 C10 -177.6(3) . . . . ?
O2 C10 C21 C12 -168.3(4) . . . . ?
O4 C10 C21 C12 9.9(5) . . . . ?
O2 C10 C21 C20 10.1(6) . . . . ?
O4 C10 C21 C20 -171.7(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
N-[(1-naphthoyl)oxy]-N-ethynyl-N-p-toluenesulfonamide
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/cyclohexane'
