#------------------------------------------------------------------------------
#$Date: 2020-08-06 16:00:53 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254898 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126667.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_7126667
loop_
_publ_author_name
'Mishra, Debashish'
'Borah, Arun Jyoti'
'Phukan, Pinakinee'
'Hazarika, Debojit'
'Phukan, Prodeep'
_publ_section_title
;
 Unprecedented 1,3-tert-butyl migration via the C-N single bond scission
 of isonitrile: an expedient metal-free route to N-sulfonyl amidines.
;
_journal_issue                   60
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              8408
_journal_page_last               8411
_journal_paper_doi               10.1039/d0cc02430a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C13 H14.5 N3.5 O4 S'
_chemical_formula_weight         315.84
_chemical_melting_point          403.5(5)
_chemical_name_systematic
N-(tert-butyl)-N'-((4-nitrophenyl)sulfonyl)acetimidamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           45
_space_group_name_Hall           'I 2 -2c'
_space_group_name_H-M_alt        'I b a 2'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-01-17 deposited with the CCDC.	2020-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.306(4)
_cell_length_b                   9.4752(9)
_cell_length_c                   11.4635(11)
_cell_measurement_reflns_used    9906
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.75
_cell_measurement_theta_min      2.26
_cell_volume                     3183.2(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29596
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.109
_diffrn_reflns_theta_min         1.390
_exptl_absorpt_coefficient_mu    0.223
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       needle
_exptl_crystal_F_000             1320
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.135
_refine_ls_abs_structure_details
;
 Flack x determined using 1789 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.008(15)
_refine_ls_extinction_coef       0.0068(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.542
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         4248
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.542
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²+0.4876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1060
_refine_ls_wR_factor_ref         0.1205
_reflns_Friedel_coverage         0.896
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                3998
_reflns_number_total             4248
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc02430a2.cif
_cod_data_source_block           ORTHO
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '403-404' was changed to
'403.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7126667.cif.
;
_cod_original_formula_sum        'C13 H14.50 N3.50 O4 S'
_cod_database_code               7126667
_shelx_shelxl_version_number     2014/7
_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'
'-x, y, z+1/2'
'x, -y, z+1/2'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1'
'x+1/2, -y+1/2, z+1'
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 0.68657(2) 0.90234(5) 0.49871(5) 0.03308(17) Uani 1 1 d . . . . .
N2 N 0.67304(6) 0.8104(2) 0.38694(15) 0.0362(4) Uani 1 1 d . . . . .
O2 O 0.48802(7) 0.8432(3) 0.7765(3) 0.0766(8) Uani 1 1 d . . . . .
O3 O 0.72554(6) 0.8481(3) 0.56151(16) 0.0531(5) Uani 1 1 d . . . . .
O4 O 0.68779(7) 1.0518(2) 0.47267(18) 0.0494(5) Uani 1 1 d . . . . .
C7 C 0.70231(6) 0.7918(2) 0.30143(18) 0.0350(4) Uani 1 1 d . . . . .
O1 O 0.53424(10) 0.8368(4) 0.9210(2) 0.0875(9) Uani 1 1 d . . . . .
C14 C 0.74984(8) 0.8523(3) 0.2982(3) 0.0570(8) Uani 1 1 d . . . . .
H14A H 0.7492 0.9482 0.3253 0.085 Uiso 1 1 calc R U . . .
H14B H 0.7612 0.8499 0.2197 0.085 Uiso 1 1 calc R U . . .
H14C H 0.7695 0.7975 0.3476 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0000 0.0000 0.4662(14) 0.188(7) Uani 1 2 d S T P . .
C9 C 0.60948(8) 0.7573(3) 0.1662(3) 0.0492(5) Uani 1 1 d . . . . .
H9A H 0.6074 0.8149 0.2349 0.074 Uiso 1 1 calc R U . . .
H9B H 0.5807 0.7116 0.1527 0.074 Uiso 1 1 calc R U . . .
H9C H 0.6170 0.8154 0.1003 0.074 Uiso 1 1 calc R U . . .
C8 C 0.64645(7) 0.6461(2) 0.18313(18) 0.0350(4) Uani 1 1 d . . . . .
N4 N 0.69076(6) 0.7150(2) 0.20946(17) 0.0382(4) Uani 1 1 d . . . . .
C4 C 0.63815(6) 0.8732(2) 0.58840(16) 0.0306(4) Uani 1 1 d . . . . .
C5 C 0.64536(7) 0.8705(2) 0.70817(18) 0.0347(4) Uani 1 1 d . . . . .
H5 H 0.6748 0.8765 0.7378 0.042 Uiso 1 1 calc R U . . .
C6 C 0.60855(7) 0.8587(2) 0.78351(19) 0.0386(4) Uani 1 1 d . . . . .
H6 H 0.6129 0.8557 0.8638 0.046 Uiso 1 1 calc R U . . .
C1 C 0.56536(7) 0.8517(2) 0.7361(2) 0.0391(4) Uani 1 1 d . . . . .
N1 N 0.52609(8) 0.8424(3) 0.8165(2) 0.0533(5) Uani 1 1 d . . . . .
C10 C 0.63334(11) 0.5437(3) 0.2796(3) 0.0530(6) Uani 1 1 d . . . . .
H10A H 0.6588 0.4833 0.2968 0.079 Uiso 1 1 calc R U . . .
H10B H 0.6079 0.4874 0.2545 0.079 Uiso 1 1 calc R U . . .
H10C H 0.6250 0.5956 0.3483 0.079 Uiso 1 1 calc R U . . .
C11 C 0.65376(12) 0.5671(4) 0.0694(3) 0.0657(8) Uani 1 1 d . . . . .
H11A H 0.6611 0.6330 0.0086 0.098 Uiso 1 1 calc R U . . .
H11B H 0.6264 0.5170 0.0491 0.098 Uiso 1 1 calc R U . . .
H11C H 0.6784 0.5012 0.0785 0.098 Uiso 1 1 calc R U . . .
C3 C 0.59428(8) 0.8663(3) 0.5422(2) 0.0417(5) Uani 1 1 d . . . . .
H3 H 0.5899 0.8684 0.4619 0.050 Uiso 1 1 calc R U . . .
C2 C 0.55695(8) 0.8561(3) 0.6170(2) 0.0464(5) Uani 1 1 d . . . . .
H2 H 0.5273 0.8524 0.5881 0.056 Uiso 1 1 calc R U . . .
C12 C 1.0000 0.0000 0.5889(10) 0.106(3) Uani 1 2 d S T P . .
N5 N 1.0000 0.0000 0.6832(12) 0.168(5) Uani 1 2 d S T P . .
H4A H 0.7123(11) 0.704(3) 0.161(3) 0.047(8) Uiso 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 0.0033 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'
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
O3 S1 O4 115.56(13) . . ?
O3 S1 N2 113.66(12) . . ?
O4 S1 N2 111.96(11) . . ?
O3 S1 C4 106.75(10) . . ?
O4 S1 C4 106.94(10) . . ?
N2 S1 C4 100.43(9) . . ?
C7 N2 S1 120.56(15) . . ?
N2 C7 N4 120.01(18) . . ?
N2 C7 C14 124.80(19) . . ?
N4 C7 C14 115.20(19) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N4 C8 C11 105.54(19) . . ?
N4 C8 C10 110.73(19) . . ?
C11 C8 C10 110.2(2) . . ?
N4 C8 C9 110.12(17) . . ?
C11 C8 C9 109.4(2) . . ?
C10 C8 C9 110.8(2) . . ?
C7 N4 C8 128.82(18) . . ?
C7 N4 H4A 113(2) . . ?
C8 N4 H4A 118(2) . . ?
C5 C4 C3 121.05(19) . . ?
C5 C4 S1 116.99(15) . . ?
C3 C4 S1 121.71(16) . . ?
C6 C5 C4 119.91(19) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C1 C6 C5 118.22(19) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6 C1 C2 123.3(2) . . ?
C6 C1 N1 118.2(2) . . ?
C2 C1 N1 118.5(2) . . ?
O2 N1 O1 123.6(3) . . ?
O2 N1 C1 118.9(3) . . ?
O1 N1 C1 117.5(2) . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C1 C2 C3 117.9(2) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
N5 C12 C13 180.0 . . ?
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 O3 1.4445(17) . ?
S1 O4 1.447(2) . ?
S1 N2 1.5995(17) . ?
S1 C4 1.774(2) . ?
N2 C7 1.314(3) . ?
O2 N1 1.206(3) . ?
C7 N4 1.325(3) . ?
C7 C14 1.507(3) . ?
O1 N1 1.223(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 C12 1.41(2) . ?
C9 C8 1.523(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 N4 1.484(3) . ?
C8 C11 1.519(3) . ?
C8 C10 1.521(3) . ?
N4 H4A 0.85(3) . ?
C4 C5 1.389(3) . ?
C4 C3 1.392(3) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.379(3) . ?
C6 H6 0.9300 . ?
C1 C2 1.388(3) . ?
C1 N1 1.477(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C3 C2 1.393(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C12 N5 1.081(15) . ?
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
O3 S1 N2 C7 -59.9(2) . . . . ?
O4 S1 N2 C7 73.3(2) . . . . ?
C4 S1 N2 C7 -173.49(18) . . . . ?
S1 N2 C7 N4 179.78(17) . . . . ?
S1 N2 C7 C14 -0.2(3) . . . . ?
N2 C7 N4 C8 2.8(4) . . . . ?
C14 C7 N4 C8 -177.3(2) . . . . ?
C11 C8 N4 C7 -177.3(3) . . . . ?
C10 C8 N4 C7 -58.1(3) . . . . ?
C9 C8 N4 C7 64.7(3) . . . . ?
O3 S1 C4 C5 28.4(2) . . . . ?
O4 S1 C4 C5 -95.81(18) . . . . ?
N2 S1 C4 C5 147.22(17) . . . . ?
O3 S1 C4 C3 -157.3(2) . . . . ?
O4 S1 C4 C3 78.5(2) . . . . ?
N2 S1 C4 C3 -38.5(2) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
S1 C4 C5 C6 175.19(16) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C5 C6 C1 C2 -0.2(4) . . . . ?
C5 C6 C1 N1 -178.7(2) . . . . ?
C6 C1 N1 O2 176.3(3) . . . . ?
C2 C1 N1 O2 -2.2(4) . . . . ?
C6 C1 N1 O1 -2.4(4) . . . . ?
C2 C1 N1 O1 179.1(3) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
S1 C4 C3 C2 -174.2(2) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
N1 C1 C2 C3 179.4(2) . . . . ?
C4 C3 C2 C1 -0.7(4) . . . . ?
