#------------------------------------------------------------------------------
#$Date: 2019-11-17 08:28:20 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/89/1548945.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_1548945
loop_
_publ_author_name
'Giri, Sovan Sundar'
'Liu, Rai-Shung'
_publ_section_title
;
 Gold-catalyzed [4+3]- and [4+2]-annulations of 3-en-1-ynamides with
 isoxazoles via novel 6π-electrocyclizations of 3-azahepta trienyl
 cations.
;
_journal_issue                   11
_journal_name_full               'Chemical science'
_journal_page_first              2991
_journal_page_last               2995
_journal_paper_doi               10.1039/c8sc00232k
_journal_volume                  9
_journal_year                    2018
_chemical_formula_moiety         'C18 H22 N2 O3 S'
_chemical_formula_sum            'C18 H22 N2 O3 S'
_chemical_formula_weight         346.44
_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_Hall  '-P 2ybc'
_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
;
2017-12-06 deposited with the CCDC.
2018-02-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.241(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.3308(12)
_cell_length_b                   16.1714(13)
_cell_length_c                   8.8646(8)
_cell_measurement_reflns_used    3678
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.61
_cell_measurement_theta_min      2.628
_cell_volume                     1762.8(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'D8 Venture'
_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  0.1020
_diffrn_reflns_av_sigmaI/netI    0.0842
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            14290
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.8885
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0527P)²+1.4791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1300
_refine_ls_wR_factor_ref         0.1630
_reflns_number_gt                1955
_reflns_number_total             3096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8sc00232k2.cif
_cod_data_source_block           d19315
_cod_depositor_comments
'Adding full bibliography for 1548943--1548948.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1548945
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1885(3) 0.4274(2) 0.6765(4) 0.0380(8) Uani 1 1 d . . .
C2 C 0.0816(3) 0.4008(3) 0.6610(5) 0.0613(12) Uani 1 1 d . . .
H2 H 0.0464 0.3923 0.5633 0.074 Uiso 1 1 calc R . .
C3 C 0.0269(3) 0.3866(3) 0.7879(5) 0.0659(13) Uani 1 1 d . . .
H3 H -0.0463 0.3679 0.7759 0.079 Uiso 1 1 calc R . .
C4 C 0.0740(3) 0.3985(2) 0.9314(5) 0.0472(10) Uani 1 1 d . . .
C5 C 0.0146(4) 0.3819(3) 1.0706(5) 0.0646(12) Uani 1 1 d . . .
H5A H -0.0634 0.3912 1.0478 0.097 Uiso 1 1 calc R . .
H5B H 0.0418 0.4192 1.1520 0.097 Uiso 1 1 calc R . .
H5C H 0.0268 0.3244 1.1026 0.097 Uiso 1 1 calc R . .
C6 C 0.1813(3) 0.4262(2) 0.9454(5) 0.0481(10) Uani 1 1 d . . .
H6 H 0.2160 0.4354 1.0433 0.058 Uiso 1 1 calc R . .
C7 C 0.2378(3) 0.4406(2) 0.8197(4) 0.0445(9) Uani 1 1 d . . .
H7 H 0.3108 0.4595 0.8314 0.053 Uiso 1 1 calc R . .
C8 C 0.2453(3) 0.2912(2) 0.3996(5) 0.0527(11) Uani 1 1 d . . .
H8A H 0.2003 0.3186 0.3187 0.079 Uiso 1 1 calc R . .
H8B H 0.1984 0.2662 0.4716 0.079 Uiso 1 1 calc R . .
H8C H 0.2894 0.2481 0.3561 0.079 Uiso 1 1 calc R . .
C9 C 0.4053(3) 0.3202(2) 0.5781(4) 0.0341(8) Uani 1 1 d . . .
C10 C 0.4864(3) 0.3697(2) 0.6487(4) 0.0361(8) Uani 1 1 d . . .
H10 H 0.4864 0.4278 0.6327 0.043 Uiso 1 1 calc R . .
C11 C 0.5671(3) 0.3327(2) 0.7427(4) 0.0353(8) Uani 1 1 d . . .
C12 C 0.6562(3) 0.3858(2) 0.8180(4) 0.0483(10) Uani 1 1 d . . .
H12A H 0.7254 0.3725 0.7761 0.072 Uiso 1 1 calc R . .
H12B H 0.6620 0.3751 0.9271 0.072 Uiso 1 1 calc R . .
H12C H 0.6389 0.4442 0.7997 0.072 Uiso 1 1 calc R . .
C13 C 0.5663(3) 0.2466(2) 0.7599(4) 0.0338(8) Uani 1 1 d . . .
C14 C 0.4857(3) 0.2017(2) 0.6770(4) 0.0363(8) Uani 1 1 d . . .
C15 C 0.4817(3) 0.1088(2) 0.6783(5) 0.0488(10) Uani 1 1 d . . .
H15A H 0.4329 0.0894 0.5934 0.073 Uiso 1 1 calc R . .
H15B H 0.4548 0.0898 0.7736 0.073 Uiso 1 1 calc R . .
H15C H 0.5548 0.0867 0.6686 0.073 Uiso 1 1 calc R . .
C16 C 0.6521(3) 0.2042(2) 0.8640(4) 0.0380(8) Uani 1 1 d . A .
H16A H 0.6641 0.2378 0.9572 0.046 Uiso 1 1 calc R . .
H16B H 0.6233 0.1499 0.8937 0.046 Uiso 1 1 calc R . .
C17 C 0.7599(3) 0.1905(2) 0.7999(4) 0.0445(9) Uani 1 1 d . . .
C18 C 0.8508(3) 0.1630(3) 0.9069(4) 0.0532(11) Uani 1 1 d . A .
H18A H 0.9064 0.1358 0.8507 0.080 Uiso 1 1 calc R . .
H18B H 0.8235 0.1239 0.9797 0.080 Uiso 1 1 calc R . .
H18C H 0.8828 0.2109 0.9611 0.080 Uiso 1 1 calc R . .
N1 N 0.3178(2) 0.35282(16) 0.4790(3) 0.0387(7) Uani 1 1 d . . .
N2 N 0.4050(2) 0.23843(16) 0.5904(3) 0.0362(7) Uani 1 1 d . . .
O1 O 0.34383(19) 0.50184(14) 0.5500(3) 0.0474(7) Uani 1 1 d . . .
O2 O 0.1829(2) 0.45732(15) 0.3883(3) 0.0531(7) Uani 1 1 d . . .
O3 O 0.7826(4) 0.2193(4) 0.6752(6) 0.0458(14) Uiso 0.50 1 d P A 1
O3' O 0.7613(4) 0.1832(3) 0.6601(6) 0.0417(13) Uiso 0.50 1 d P A 2
S1 S 0.25969(7) 0.44219(5) 0.51379(11) 0.0413(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 119.3(4)
C7 C1 S1 121.3(3)
C2 C1 S1 119.4(3)
C3 C2 C1 119.5(4)
C3 C2 H2 120.2
C1 C2 H2 120.2
C4 C3 C2 122.4(4)
C4 C3 H3 118.8
C2 C3 H3 118.8
C3 C4 C6 117.5(4)
C3 C4 C5 122.5(4)
C6 C4 C5 120.0(4)
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(4)
C7 C6 H6 119.5
C4 C6 H6 119.5
C6 C7 C1 120.2(3)
C6 C7 H7 119.9
C1 C7 H7 119.9
N1 C8 H8A 109.5
N1 C8 H8B 109.5
H8A C8 H8B 109.5
N1 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C9 C10 122.8(3)
N2 C9 N1 114.1(3)
C10 C9 N1 123.0(3)
C11 C10 C9 118.8(3)
C11 C10 H10 120.6
C9 C10 H10 120.6
C10 C11 C13 119.0(3)
C10 C11 C12 119.1(3)
C13 C11 C12 121.8(3)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C14 C13 C11 118.0(3)
C14 C13 C16 121.6(3)
C11 C13 C16 120.4(3)
N2 C14 C13 122.5(3)
N2 C14 C15 114.9(3)
C13 C14 C15 122.6(3)
C14 C15 H15A 109.5
C14 C15 H15B 109.5
H15A C15 H15B 109.5
C14 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C17 C16 C13 115.7(3)
C17 C16 H16A 108.3
C13 C16 H16A 108.3
C17 C16 H16B 108.3
C13 C16 H16B 108.3
H16A C16 H16B 107.4
O3' C17 O3 30.2(3)
O3' C17 C18 122.8(4)
O3 C17 C18 118.0(4)
O3' C17 C16 117.9(4)
O3 C17 C16 122.9(4)
C18 C17 C16 116.8(3)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C9 N1 C8 116.3(3)
C9 N1 S1 121.4(2)
C8 N1 S1 115.0(2)
C9 N2 C14 118.6(3)
O2 S1 O1 119.06(15)
O2 S1 N1 106.02(15)
O1 S1 N1 108.27(15)
O2 S1 C1 108.63(17)
O1 S1 C1 107.72(16)
N1 S1 C1 106.50(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C7 1.383(5)
C1 C2 1.384(5)
C1 S1 1.759(4)
C2 C3 1.373(6)
C2 H2 0.9500
C3 C4 1.372(5)
C3 H3 0.9500
C4 C6 1.394(5)
C4 C5 1.505(6)
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.377(5)
C6 H6 0.9500
C7 H7 0.9500
C8 N1 1.480(4)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 N2 1.327(4)
C9 C10 1.392(4)
C9 N1 1.441(4)
C10 C11 1.386(4)
C10 H10 0.9500
C11 C13 1.400(5)
C11 C12 1.510(5)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.395(4)
C13 C16 1.515(4)
C14 N2 1.349(4)
C14 C15 1.503(5)
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
C16 C17 1.500(5)
C16 H16A 0.9900
C16 H16B 0.9900
C17 O3' 1.246(6)
C17 O3 1.250(6)
C17 C18 1.483(5)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
N1 S1 1.652(3)
O1 S1 1.435(2)
O2 S1 1.427(2)
