#------------------------------------------------------------------------------
#$Date: 2023-06-30 00:57:15 +0300 (Fri, 30 Jun 2023) $
#$Revision: 284716 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/18/7131800.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131800
loop_
_publ_author_name
'Kagami, Kentaro'
'Liang, Xueying'
'Ishibashi, Nanako'
'Ohrui, Sayaka'
'Tayu, Masanori'
'Saito, Nozomi'
_publ_section_title
;
 Synthesis of N-(acyloxy)-N-alkynylamides via
 generation of "C₂" from hypervalent alkynyliodane and a weak
 base.
;
_journal_issue                   53
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              8274
_journal_page_last               8277
_journal_paper_doi               10.1039/d3cc01403g
_journal_volume                  59
_journal_year                    2023
_chemical_formula_moiety         'C20 H15 N O4 S'
_chemical_formula_sum            'C20 H15 N O4 S'
_chemical_formula_weight         365.40
_chemical_melting_point          371(2)
_chemical_name_systematic
N-[(1-naphthoyl)oxy]-N-ethynyl-N-p-toluenesulfonamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccdc.csd.cc2cmzbb
_audit_update_record
;
2022-08-01 deposited with the CCDC.	2023-06-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.096(7)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   15.1494(16)
_cell_length_b                   15.0265(16)
_cell_length_c                   7.6701(8)
_cell_measurement_reflns_used    7000
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      2.94
_cell_volume                     1713.4(3)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.3'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2019)'
_computing_structure_refinement  'SHELXL Version 2016/4 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      93
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1198
_diffrn_reflns_av_unetI/netI     0.0881
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19514
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         2.973
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.907
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_T_min  0.594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             760.00
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dichloromethane/cyclohexane'
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1105P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2045
_refine_ls_wR_factor_ref         0.2292
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2029
_reflns_number_total             3100
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            d3cc01403g2.cif
_cod_data_source_block           03KK038B2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '369-373' was changed to
'371(2)' -- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_database_code               7131800
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
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 . . . . .
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)
;
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_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_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) . . . . ?
