#------------------------------------------------------------------------------
#$Date: 2019-11-23 19:39:39 +0200 (Sat, 23 Nov 2019) $
#$Revision: 234689 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/53/7125302.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_7125302
loop_
_publ_author_name
'Liao, Zhen-Yuan'
'Liao, Pen-Yuan'
'Chien, Tun-Cheng'
_publ_section_title
;
 CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in
 N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates.
;
_journal_issue                   100
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14404
_journal_page_last               14407
_journal_paper_doi               10.1039/c6cc08601b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C16 H12 N2 O2 S'
_chemical_formula_sum            'C16 H12 N2 O2 S'
_chemical_formula_weight         296.34
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-10-26 deposited with the CCDC.
2016-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.384(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0829(15)
_cell_length_b                   10.2351(14)
_cell_length_c                   15.664(2)
_cell_measurement_reflns_used    808
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      22.63
_cell_measurement_theta_min      3.01
_cell_volume                     1444.1(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_sigmaI/netI    0.0839
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9899
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.9932
_exptl_absorpt_correction_T_min  0.9492
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0491P)²+0.2463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1274
_reflns_number_gt                1556
_reflns_number_total             2547
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc08601b3.cif
_cod_data_source_block           a15781
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7125302
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.3412(3) 0.1652(3) 0.1185(2) 0.0309(8) Uani 1 1 d .
C2 C 0.4047(4) 0.0408(3) 0.1177(2) 0.0409(9) Uani 1 1 d .
H2 H 0.4831 0.0162 0.1608 0.049 Uiso 1 1 calc R
C3 C 0.3516(4) -0.0459(3) 0.0534(2) 0.0488(10) Uani 1 1 d .
H3 H 0.3942 -0.1306 0.0530 0.059 Uiso 1 1 calc R
C4 C 0.2373(4) -0.0122(3) -0.0108(2) 0.0403(9) Uani 1 1 d .
C5 C 0.1822(4) -0.1052(4) -0.0832(3) 0.0600(12) Uani 1 1 d .
H5A H 0.1019 -0.0636 -0.1215 0.090 Uiso 1 1 calc R
H5B H 0.1451 -0.1852 -0.0590 0.090 Uiso 1 1 calc R
H5C H 0.2640 -0.1269 -0.1158 0.090 Uiso 1 1 calc R
C6 C 0.1744(4) 0.1120(3) -0.0082(2) 0.0416(9) Uani 1 1 d .
H6 H 0.0950 0.1361 -0.0509 0.050 Uiso 1 1 calc R
C7 C 0.2260(4) 0.2008(3) 0.0557(2) 0.0385(9) Uani 1 1 d .
H7 H 0.1829 0.2853 0.0564 0.046 Uiso 1 1 calc R
C8 C 0.1717(3) 0.2233(3) 0.2932(2) 0.0293(8) Uani 1 1 d .
C9 C 0.0604(4) 0.3057(3) 0.2540(2) 0.0348(9) Uani 1 1 d .
H9 H 0.0804 0.3702 0.2135 0.042 Uiso 1 1 calc R
C10 C -0.0799(4) 0.2891(4) 0.2770(2) 0.0430(10) Uani 1 1 d .
H10 H -0.1583 0.3431 0.2512 0.052 Uiso 1 1 calc R
C11 C -0.1103(4) 0.1951(3) 0.3373(2) 0.0439(10) Uani 1 1 d .
H11 H -0.2086 0.1862 0.3511 0.053 Uiso 1 1 calc R
C12 C 0.0006(4) 0.1152(3) 0.3768(2) 0.0376(9) Uani 1 1 d .
H12 H -0.0198 0.0523 0.4183 0.045 Uiso 1 1 calc R
C13 C 0.1437(3) 0.1292(3) 0.3541(2) 0.0294(8) Uani 1 1 d .
C14 C 0.2853(4) 0.0676(3) 0.3832(2) 0.0307(8) Uani 1 1 d .
C15 C 0.3899(4) 0.1223(3) 0.3401(2) 0.0341(8) Uani 1 1 d .
H15 H 0.4916 0.0978 0.3461 0.041 Uiso 1 1 calc R
C16 C 0.3119(4) -0.0298(3) 0.4498(2) 0.0378(9) Uani 1 1 d .
N1 N 0.3255(3) 0.2196(2) 0.28589(16) 0.0312(7) Uani 1 1 d .
N2 N 0.3305(3) -0.1058(3) 0.5036(2) 0.0569(10) Uani 1 1 d .
O1 O 0.3419(2) 0.40154(19) 0.18142(15) 0.0415(6) Uani 1 1 d .
O2 O 0.5603(2) 0.2584(2) 0.22601(15) 0.0453(7) Uani 1 1 d .
S1 S 0.40429(9) 0.27468(8) 0.20094(6) 0.0341(3) 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 0.0033 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
C7 C1 C2 120.5(3)
C7 C1 S1 120.0(3)
C2 C1 S1 119.5(3)
C3 C2 C1 119.0(3)
C3 C2 H2 120.5
C1 C2 H2 120.5
C2 C3 C4 121.7(3)
C2 C3 H3 119.2
C4 C3 H3 119.2
C3 C4 C6 118.4(3)
C3 C4 C5 121.9(3)
C6 C4 C5 119.8(3)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C7 C6 C4 121.0(3)
C7 C6 H6 119.5
C4 C6 H6 119.5
C6 C7 C1 119.5(3)
C6 C7 H7 120.2
C1 C7 H7 120.2
C9 C8 C13 122.0(3)
C9 C8 N1 130.3(3)
C13 C8 N1 107.6(3)
C10 C9 C8 116.9(3)
C10 C9 H9 121.6
C8 C9 H9 121.6
C9 C10 C11 122.0(3)
C9 C10 H10 119.0
C11 C10 H10 119.0
C12 C11 C10 120.9(3)
C12 C11 H11 119.5
C10 C11 H11 119.5
C11 C12 C13 118.3(3)
C11 C12 H12 120.9
C13 C12 H12 120.9
C12 C13 C8 120.0(3)
C12 C13 C14 133.7(3)
C8 C13 C14 106.3(3)
C15 C14 C16 125.7(3)
C15 C14 C13 108.3(3)
C16 C14 C13 126.0(3)
C14 C15 N1 109.5(3)
C14 C15 H15 125.3
N1 C15 H15 125.3
N2 C16 C14 178.4(4)
C15 N1 C8 108.2(3)
C15 N1 S1 122.3(2)
C8 N1 S1 125.3(2)
O2 S1 O1 120.96(13)
O2 S1 N1 104.49(13)
O1 S1 N1 105.95(14)
O2 S1 C1 110.28(15)
O1 S1 C1 109.86(15)
N1 S1 C1 103.67(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.390(4)
C1 C2 1.398(4)
C1 S1 1.751(3)
C2 C3 1.381(4)
C2 H2 0.9500
C3 C4 1.393(5)
C3 H3 0.9500
C4 C6 1.396(4)
C4 C5 1.516(4)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.388(4)
C6 H6 0.9500
C7 H7 0.9500
C8 C9 1.397(4)
C8 C13 1.402(4)
C8 N1 1.417(4)
C9 C10 1.378(5)
C9 H9 0.9500
C10 C11 1.400(5)
C10 H10 0.9500
C11 C12 1.381(4)
C11 H11 0.9500
C12 C13 1.398(4)
C12 H12 0.9500
C13 C14 1.452(4)
C14 C15 1.355(4)
C14 C16 1.441(4)
C15 N1 1.389(4)
C15 H15 0.9500
C16 N2 1.143(4)
N1 S1 1.687(3)
O1 S1 1.434(2)
O2 S1 1.431(2)
