#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/43/1554319.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_1554319
loop_
_publ_author_name
'Jiang, Bo'
'Wei, Yin'
'Shi, Min'
_publ_section_title
;
 Gold- and silver-catalyzed intramolecular annulation and rearrangement of
 aniline-linked 1,6-enynes containing methylenecyclopropanes
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2091
_journal_paper_doi               10.1039/C8QO00358K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C26 H23 N O2 S'
_chemical_formula_weight         413.51
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2017-09-20 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.440(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7526(16)
_cell_length_b                   13.4984(19)
_cell_length_c                   13.5265(19)
_cell_measurement_reflns_used    3914
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      52.037
_cell_measurement_theta_min      4.598
_cell_volume                     2143.9(5)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.999
_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  0.1055
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27670
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.132
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0015(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3758
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1633
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1064P)²+0.9552P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1824
_refine_ls_wR_factor_ref         0.2426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1875
_reflns_number_total             3758
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8qo00358k2.cif
_cod_data_source_block           mo_d8v17381_0m
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               1554319
_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. 
;
_shelx_estimated_absorpt_t_min   0.983
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
S1 S 0.18845(11) 0.76307(11) 0.33500(11) 0.0821(6) Uani 1 1 d . .
N1 N 0.2474(3) 0.8600(3) 0.3914(3) 0.0771(12) Uani 1 1 d . .
O1 O 0.1545(3) 0.7962(3) 0.2379(3) 0.1122(14) Uani 1 1 d . .
O2 O 0.1067(3) 0.7256(3) 0.3993(3) 0.1019(13) Uani 1 1 d . .
C1 C 0.2929(4) 0.8453(3) 0.4906(4) 0.0665(13) Uani 1 1 d . .
C2 C 0.2219(5) 0.8345(4) 0.5694(4) 0.0811(15) Uani 1 1 d . .
H2 H 0.1433 0.8338 0.5580 0.097 Uiso 1 1 calc R U
C3 C 0.2675(5) 0.8249(4) 0.6644(4) 0.0871(17) Uani 1 1 d . .
H3 H 0.2195 0.8187 0.7169 0.105 Uiso 1 1 calc R U
C4 C 0.3836(5) 0.8245(4) 0.6822(4) 0.0823(15) Uani 1 1 d . .
H4 H 0.4138 0.8182 0.7466 0.099 Uiso 1 1 calc R U
C5 C 0.4552(4) 0.8334(4) 0.6042(4) 0.0733(14) Uani 1 1 d . .
H5 H 0.5336 0.8321 0.6165 0.088 Uiso 1 1 calc R U
C6 C 0.4113(4) 0.8443(3) 0.5069(3) 0.0644(12) Uani 1 1 d . .
C7 C 0.4852(4) 0.8586(3) 0.4225(3) 0.0618(12) Uani 1 1 d . .
C8 C 0.4408(4) 0.8976(4) 0.3376(4) 0.0689(13) Uani 1 1 d . .
C9 C 0.3185(4) 0.9259(4) 0.3332(4) 0.0764(14) Uani 1 1 d . .
H9A H 0.3113 0.9932 0.3575 0.092 Uiso 1 1 calc R U
H9B H 0.2904 0.9250 0.2647 0.092 Uiso 1 1 calc R U
C10 C 0.4991(5) 0.9147(4) 0.2469(4) 0.0830(15) Uani 1 1 d . .
C11 C 0.6130(6) 0.9082(6) 0.2142(5) 0.129(3) Uani 1 1 d . .
H11A H 0.6428 0.8412 0.2138 0.154 Uiso 1 1 calc R U
H11B H 0.6659 0.9528 0.2487 0.154 Uiso 1 1 calc R U
C12 C 0.5698(5) 0.9470(5) 0.1078(5) 0.113(2) Uani 1 1 d . .
H12A H 0.6003 1.0108 0.0891 0.135 Uiso 1 1 calc R U
H12B H 0.5739 0.8988 0.0549 0.135 Uiso 1 1 calc R U
C13 C 0.4609(6) 0.9512(6) 0.1550(5) 0.118(2) Uani 1 1 d . .
H13 H 0.3891 0.9716 0.1315 0.142 Uiso 1 1 calc R U
C14 C 0.6060(4) 0.8271(4) 0.4372(3) 0.0660(13) Uani 1 1 d . .
C15 C 0.6942(5) 0.8937(5) 0.4422(4) 0.0874(16) Uani 1 1 d . .
H15 H 0.6785 0.9611 0.4373 0.105 Uiso 1 1 calc R U
C16 C 0.8053(6) 0.8628(7) 0.4543(4) 0.107(2) Uani 1 1 d . .
H16 H 0.8638 0.9092 0.4578 0.128 Uiso 1 1 calc R U
C17 C 0.8300(5) 0.7658(7) 0.4611(4) 0.109(2) Uani 1 1 d . .
H17 H 0.9054 0.7452 0.4673 0.131 Uiso 1 1 calc R U
C18 C 0.7437(6) 0.6969(6) 0.4589(5) 0.114(2) Uani 1 1 d . .
H18 H 0.7602 0.6298 0.4656 0.137 Uiso 1 1 calc R U
C19 C 0.6329(5) 0.7284(4) 0.4465(4) 0.0886(17) Uani 1 1 d . .
H19 H 0.5746 0.6817 0.4444 0.106 Uiso 1 1 calc R U
C20 C 0.2941(4) 0.6718(4) 0.3223(4) 0.0693(13) Uani 1 1 d . .
C21 C 0.3160(4) 0.6060(4) 0.3985(4) 0.0780(15) Uani 1 1 d . .
H21 H 0.2752 0.6093 0.4558 0.094 Uiso 1 1 calc R U
C22 C 0.3995(5) 0.5347(4) 0.3886(4) 0.0875(16) Uani 1 1 d . .
H22 H 0.4122 0.4889 0.4393 0.105 Uiso 1 1 calc R U
C23 C 0.4635(5) 0.5295(5) 0.3074(5) 0.0904(17) Uani 1 1 d . .
C24 C 0.4398(5) 0.5965(5) 0.2325(5) 0.0980(19) Uani 1 1 d . .
H24 H 0.4817 0.5937 0.1757 0.118 Uiso 1 1 calc R U
C25 C 0.3561(5) 0.6675(5) 0.2387(4) 0.0853(16) Uani 1 1 d . .
H25 H 0.3418 0.7118 0.1870 0.102 Uiso 1 1 calc R U
C26 C 0.5577(5) 0.4546(5) 0.2982(6) 0.131(3) Uani 1 1 d . .
H26A H 0.5694 0.4421 0.2296 0.197 Uiso 1 1 calc R U
H26B H 0.5370 0.3941 0.3301 0.197 Uiso 1 1 calc R U
H26C H 0.6266 0.4800 0.3293 0.197 Uiso 1 1 calc R U
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
O2 S1 O1 120.4(2)
O2 S1 N1 106.3(2)
O1 S1 N1 105.8(2)
O2 S1 C20 108.0(3)
O1 S1 C20 107.4(3)
N1 S1 C20 108.4(2)
C1 N1 C9 112.7(4)
C1 N1 S1 116.9(3)
C9 N1 S1 117.9(3)
C2 C1 C6 120.2(5)
C2 C1 N1 121.3(4)
C6 C1 N1 118.4(4)
C3 C2 C1 120.2(5)
C3 C2 H2 119.9
C1 C2 H2 119.9
C4 C3 C2 120.5(5)
C4 C3 H3 119.7
C2 C3 H3 119.7
C3 C4 C5 119.8(5)
C3 C4 H4 120.1
C5 C4 H4 120.1
C4 C5 C6 121.0(5)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 C1 118.2(4)
C5 C6 C7 122.4(4)
C1 C6 C7 119.4(4)
C8 C7 C6 119.4(4)
C8 C7 C14 123.9(4)
C6 C7 C14 116.7(4)
C7 C8 C10 127.1(5)
C7 C8 C9 118.3(4)
C10 C8 C9 114.6(5)
N1 C9 C8 113.1(4)
N1 C9 H9A 109.0
C8 C9 H9A 109.0
N1 C9 H9B 109.0
C8 C9 H9B 109.0
H9A C9 H9B 107.8
C13 C10 C11 91.0(5)
C13 C10 C8 131.7(6)
C11 C10 C8 137.3(6)
C10 C11 C12 89.6(5)
C10 C11 H11A 113.7
C12 C11 H11A 113.7
C10 C11 H11B 113.7
C12 C11 H11B 113.7
H11A C11 H11B 111.0
C13 C12 C11 82.4(5)
C13 C12 H12A 114.9
C11 C12 H12A 114.9
C13 C12 H12B 114.9
C11 C12 H12B 114.9
H12A C12 H12B 112.0
C10 C13 C12 97.0(6)
C10 C13 H13 131.5
C12 C13 H13 131.5
C15 C14 C19 117.4(5)
C15 C14 C7 122.3(5)
C19 C14 C7 120.3(4)
C14 C15 C16 121.3(6)
C14 C15 H15 119.3
C16 C15 H15 119.3
C17 C16 C15 120.3(6)
C17 C16 H16 119.8
C15 C16 H16 119.8
C16 C17 C18 120.1(6)
C16 C17 H17 120.0
C18 C17 H17 120.0
C19 C18 C17 119.2(7)
C19 C18 H18 120.4
C17 C18 H18 120.4
C18 C19 C14 121.7(6)
C18 C19 H19 119.2
C14 C19 H19 119.2
C25 C20 C21 120.1(5)
C25 C20 S1 120.7(4)
C21 C20 S1 119.2(4)
C20 C21 C22 119.1(5)
C20 C21 H21 120.4
C22 C21 H21 120.4
C23 C22 C21 122.2(6)
C23 C22 H22 118.9
C21 C22 H22 118.9
C22 C23 C24 117.3(6)
C22 C23 C26 122.3(7)
C24 C23 C26 120.4(7)
C23 C24 C25 122.2(5)
C23 C24 H24 118.9
C25 C24 H24 118.9
C20 C25 C24 119.0(6)
C20 C25 H25 120.5
C24 C25 H25 120.5
C23 C26 H26A 109.5
C23 C26 H26B 109.5
H26A C26 H26B 109.5
C23 C26 H26C 109.5
H26A C26 H26C 109.5
H26B C26 H26C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O2 1.417(4)
S1 O1 1.429(4)
S1 N1 1.652(5)
S1 C20 1.763(5)
N1 C1 1.438(6)
N1 C9 1.471(6)
C1 C2 1.389(6)
C1 C6 1.400(6)
C2 C3 1.377(7)
C2 H2 0.9300
C3 C4 1.375(7)
C3 H3 0.9300
C4 C5 1.383(6)
C4 H4 0.9300
C5 C6 1.400(6)
C5 H5 0.9300
C6 C7 1.476(6)
C7 C8 1.348(6)
C7 C14 1.486(6)
C8 C10 1.450(7)
C8 C9 1.486(6)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C13 1.394(8)
C10 C11 1.430(8)
C11 C12 1.595(8)
C11 H11A 0.9700
C11 H11B 0.9700
C12 C13 1.456(8)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13 0.9300
C14 C15 1.371(7)
C14 C19 1.375(7)
C15 C16 1.374(8)
C15 H15 0.9300
C16 C17 1.343(9)
C16 H16 0.9300
C17 C18 1.376(9)
C17 H17 0.9300
C18 C19 1.373(8)
C18 H18 0.9300
C19 H19 0.9300
C20 C25 1.372(7)
C20 C21 1.377(7)
C21 C22 1.384(7)
C21 H21 0.9300
C22 C23 1.360(7)
C22 H22 0.9300
C23 C24 1.378(8)
C23 C26 1.508(8)
C24 C25 1.379(8)
C24 H24 0.9300
C25 H25 0.9300
C26 H26A 0.9600
C26 H26B 0.9600
C26 H26C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9B O1 0.97 2.38 2.869(7) 110.8
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
O2 S1 N1 C1 52.9(4)
O1 S1 N1 C1 -177.9(3)
C20 S1 N1 C1 -63.0(4)
O2 S1 N1 C9 -167.6(3)
O1 S1 N1 C9 -38.5(4)
C20 S1 N1 C9 76.5(4)
C9 N1 C1 C2 145.1(5)
S1 N1 C1 C2 -73.4(5)
C9 N1 C1 C6 -33.4(6)
S1 N1 C1 C6 108.2(4)
C6 C1 C2 C3 1.3(8)
N1 C1 C2 C3 -177.1(5)
C1 C2 C3 C4 -0.9(8)
C2 C3 C4 C5 -0.2(8)
C3 C4 C5 C6 0.9(8)
C4 C5 C6 C1 -0.5(7)
C4 C5 C6 C7 177.2(4)
C2 C1 C6 C5 -0.6(7)
N1 C1 C6 C5 177.8(4)
C2 C1 C6 C7 -178.4(4)
N1 C1 C6 C7 0.1(7)
C5 C6 C7 C8 -160.2(5)
C1 C6 C7 C8 17.4(7)
C5 C6 C7 C14 20.4(7)
C1 C6 C7 C14 -162.0(4)
C6 C7 C8 C10 -178.4(5)
C14 C7 C8 C10 0.9(8)
C6 C7 C8 C9 0.8(7)
C14 C7 C8 C9 -179.9(4)
C1 N1 C9 C8 49.9(6)
S1 N1 C9 C8 -91.1(5)
C7 C8 C9 N1 -34.2(6)
C10 C8 C9 N1 145.1(4)
C7 C8 C10 C13 177.7(6)
C9 C8 C10 C13 -1.5(9)
C7 C8 C10 C11 -6.5(10)
C9 C8 C10 C11 174.3(7)
C13 C10 C11 C12 -1.5(5)
C8 C10 C11 C12 -178.4(6)
C10 C11 C12 C13 1.4(5)
C11 C10 C13 C12 1.6(6)
C8 C10 C13 C12 178.8(6)
C11 C12 C13 C10 -1.5(5)
C8 C7 C14 C15 69.3(7)
C6 C7 C14 C15 -111.4(5)
C8 C7 C14 C19 -110.9(6)
C6 C7 C14 C19 68.5(6)
C19 C14 C15 C16 1.1(8)
C7 C14 C15 C16 -179.0(5)
C14 C15 C16 C17 0.3(9)
C15 C16 C17 C18 -1.9(10)
C16 C17 C18 C19 2.0(10)
C17 C18 C19 C14 -0.6(9)
C15 C14 C19 C18 -1.0(8)
C7 C14 C19 C18 179.2(5)
O2 S1 C20 C25 153.3(4)
O1 S1 C20 C25 22.0(5)
N1 S1 C20 C25 -91.9(4)
O2 S1 C20 C21 -28.2(5)
O1 S1 C20 C21 -159.5(4)
N1 S1 C20 C21 86.6(4)
C25 C20 C21 C22 -1.2(7)
S1 C20 C21 C22 -179.6(4)
C20 C21 C22 C23 2.2(8)
C21 C22 C23 C24 -2.1(8)
C21 C22 C23 C26 177.5(5)
C22 C23 C24 C25 0.9(9)
C26 C23 C24 C25 -178.6(5)
C21 C20 C25 C24 0.1(8)
S1 C20 C25 C24 178.5(4)
C23 C24 C25 C20 0.1(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168304362
