#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:26:11 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301853 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/89/7108952.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_7108952
loop_
_publ_author_name
'Stephen J. Heffernan'
'James M. Beddoes'
'Mary F. Mahon'
'Alan J. Hennessy'
'David R. Carbery'
_publ_section_title
;
 Gold-catalysed cascade rearrangements of ynamide propargyl esters
;
_journal_name_full               Chem.Commun.
_journal_page_first              2314
_journal_paper_doi               10.1039/c3cc00273j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_sum            'C23 H21 I N2 O4'
_chemical_formula_weight         516.32
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.4740(1)
_cell_length_b                   21.0690(2)
_cell_length_c                   22.6350(2)
_cell_measurement_reflns_used    41307
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.910
_cell_volume                     4518.12(8)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Bruker AXS BV 1997-2004)'
_computing_data_reduction        'Denzo & Scalepack (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'ORTEX (P.McArdle 1995)'
_computing_publication_material  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97/2 (Sheldrick 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0493
_diffrn_reflns_av_sigmaI/netI    0.0173
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            65108
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.58
_exptl_absorpt_coefficient_mu    1.448
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tabloid
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.229
_refine_diff_density_min         -2.162
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0768
_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)+(0.0835P)²+14.8885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2137
_reflns_number_gt                3224
_reflns_number_total             3968
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc00273j.txt
_cod_data_source_block           k11dc3a
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7108952
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
I1 I -0.02282(8) 0.29613(3) 0.02846(3) 0.1187(4) Uani 1 1 d .
O1 O 0.4507(4) 0.34882(19) 0.14997(16) 0.0600(10) Uani 1 1 d .
O2 O 0.6714(5) 0.3857(3) 0.1538(2) 0.0972(17) Uani 1 1 d .
O3 O 0.4381(7) 0.4690(2) 0.2924(2) 0.0923(15) Uani 1 1 d .
O4 O 0.3637(8) 0.4594(2) 0.2004(3) 0.120(2) Uani 1 1 d .
N1 N 0.2296(8) 0.0889(2) 0.1892(3) 0.0897(19) Uani 1 1 d .
H1 H 0.1983 0.0524 0.2027 0.108 Uiso 1 1 calc R
N2 N 0.4586(5) 0.3744(2) 0.2507(2) 0.0540(10) Uani 1 1 d .
C1 C 0.0561(7) 0.2262(3) 0.0862(3) 0.0715(17) Uani 1 1 d .
C2 C -0.0311(8) 0.1764(5) 0.1006(4) 0.093(2) Uani 1 1 d .
H2 H -0.1245 0.1752 0.0854 0.111 Uiso 1 1 calc R
C3 C 0.0145(9) 0.1286(4) 0.1365(4) 0.095(3) Uani 1 1 d .
H3 H -0.0465 0.0948 0.1473 0.113 Uiso 1 1 calc R
C4 C 0.1528(8) 0.1309(3) 0.1568(3) 0.0716(17) Uani 1 1 d .
C5 C 0.2418(6) 0.1830(2) 0.1444(2) 0.0539(12) Uani 1 1 d .
C6 C 0.1911(6) 0.2317(3) 0.1085(2) 0.0577(13) Uani 1 1 d .
H6 H 0.2478 0.2676 0.0997 0.069 Uiso 1 1 calc R
C7 C 0.3758(6) 0.1708(2) 0.1716(2) 0.0564(13) Uani 1 1 d .
C8 C 0.3629(9) 0.1121(3) 0.1975(3) 0.0763(19) Uani 1 1 d .
H8 H 0.4361 0.0908 0.2182 0.092 Uiso 1 1 calc R
C9 C 0.4994(6) 0.2156(3) 0.1718(3) 0.0591(14) Uani 1 1 d .
H9 H 0.5036 0.2372 0.1325 0.071 Uiso 1 1 calc R
C10 C 0.6400(8) 0.1823(4) 0.1823(4) 0.095(2) Uani 1 1 d .
H10A H 0.7171 0.2130 0.1785 0.143 Uiso 1 1 calc R
H10B H 0.6523 0.1485 0.1530 0.143 Uiso 1 1 calc R
H10C H 0.6411 0.1639 0.2220 0.143 Uiso 1 1 calc R
C11 C 0.4779(6) 0.2654(3) 0.2184(2) 0.0536(12) Uani 1 1 d .
H11 H 0.4745 0.2518 0.2583 0.064 Uiso 1 1 calc R
C12 C 0.4634(5) 0.3270(2) 0.2079(2) 0.0495(11) Uani 1 1 d .
C13 C 0.5649(8) 0.3798(3) 0.1273(3) 0.0712(16) Uani 1 1 d .
C14 C 0.5303(9) 0.4022(4) 0.0658(3) 0.096(3) Uani 1 1 d .
H14A H 0.5138 0.3647 0.0405 0.116 Uiso 1 1 calc R
H14B H 0.4412 0.4268 0.0673 0.116 Uiso 1 1 calc R
C15 C 0.6418(8) 0.4424(3) 0.0380(3) 0.0712(16) Uani 1 1 d .
C16 C 0.7094(8) 0.4243(4) -0.0124(3) 0.0819(19) Uani 1 1 d .
H16 H 0.6893 0.3841 -0.0293 0.098 Uiso 1 1 calc R
C17 C 0.8060(10) 0.4635(5) -0.0389(3) 0.102(3) Uani 1 1 d .
H17 H 0.8535 0.4499 -0.0737 0.122 Uiso 1 1 calc R
C18 C 0.8342(10) 0.5217(5) -0.0158(4) 0.099(2) Uani 1 1 d .
H18 H 0.8982 0.5493 -0.0353 0.119 Uiso 1 1 calc R
C19 C 0.7728(13) 0.5400(4) 0.0341(5) 0.126(4) Uani 1 1 d .
H19 H 0.7937 0.5804 0.0506 0.151 Uiso 1 1 calc R
C20 C 0.6782(12) 0.4999(4) 0.0619(4) 0.126(4) Uani 1 1 d .
H20 H 0.6375 0.5125 0.0984 0.151 Uiso 1 1 calc R
C21 C 0.4152(9) 0.4354(3) 0.2433(3) 0.0767(18) Uani 1 1 d .
C22 C 0.5095(8) 0.3630(3) 0.3101(3) 0.0789(19) Uani 1 1 d .
H22A H 0.6080 0.3473 0.3100 0.095 Uiso 1 1 calc R
H22B H 0.4488 0.3323 0.3314 0.095 Uiso 1 1 calc R
C23 C 0.4993(9) 0.4291(4) 0.3370(3) 0.086(2) Uani 1 1 d .
H23A H 0.4391 0.4285 0.3727 0.103 Uiso 1 1 calc R
H23B H 0.5942 0.4449 0.3481 0.103 Uiso 1 1 calc R
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'
I I -0.4742 1.8119 '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
C13 O1 C12 116.2(4)
C21 O3 C23 110.0(5)
C4 N1 C8 109.6(5)
C4 N1 H1 125.2
C8 N1 H1 125.2
C21 N2 C12 127.0(5)
C21 N2 C22 111.8(5)
C12 N2 C22 121.1(5)
C2 C1 C6 122.3(7)
C2 C1 I1 117.9(6)
C6 C1 I1 119.8(5)
C3 C2 C1 120.9(7)
C3 C2 H2 119.5
C1 C2 H2 119.5
C2 C3 C4 118.1(7)
C2 C3 H3 121.0
C4 C3 H3 121.0
N1 C4 C3 131.3(7)
N1 C4 C5 107.1(6)
C3 C4 C5 121.6(7)
C6 C5 C4 118.8(6)
C6 C5 C7 133.5(5)
C4 C5 C7 107.6(5)
C1 C6 C5 118.1(6)
C1 C6 H6 121.0
C5 C6 H6 121.0
C8 C7 C5 105.5(6)
C8 C7 C9 129.2(6)
C5 C7 C9 125.3(5)
N1 C8 C7 110.2(6)
N1 C8 H8 124.9
C7 C8 H8 124.9
C11 C9 C7 109.6(5)
C11 C9 C10 109.4(5)
C7 C9 C10 113.0(6)
C11 C9 H9 108.2
C7 C9 H9 108.2
C10 C9 H9 108.2
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C9 124.9(5)
C12 C11 H11 117.5
C9 C11 H11 117.5
C11 C12 N2 125.5(5)
C11 C12 O1 120.0(5)
N2 C12 O1 114.5(4)
O2 C13 O1 122.5(5)
O2 C13 C14 128.5(6)
O1 C13 C14 108.9(6)
C15 C14 C13 114.5(6)
C15 C14 H14A 108.6
C13 C14 H14A 108.6
C15 C14 H14B 108.6
C13 C14 H14B 108.6
H14A C14 H14B 107.6
C16 C15 C20 117.4(7)
C16 C15 C14 121.8(7)
C20 C15 C14 120.8(7)
C15 C16 C17 120.8(7)
C15 C16 H16 119.6
C17 C16 H16 119.6
C18 C17 C16 120.3(8)
C18 C17 H17 119.8
C16 C17 H17 119.8
C19 C18 C17 120.3(8)
C19 C18 H18 119.9
C17 C18 H18 119.9
C18 C19 C20 119.6(8)
C18 C19 H19 120.2
C20 C19 H19 120.2
C15 C20 C19 121.5(8)
C15 C20 H20 119.2
C19 C20 H20 119.2
O4 C21 O3 121.2(6)
O4 C21 N2 128.4(6)
O3 C21 N2 110.4(6)
N2 C22 C23 101.4(5)
N2 C22 H22A 111.5
C23 C22 H22A 111.5
N2 C22 H22B 111.5
C23 C22 H22B 111.5
H22A C22 H22B 109.3
O3 C23 C22 106.2(5)
O3 C23 H23A 110.5
C22 C23 H23A 110.5
O3 C23 H23B 110.5
C22 C23 H23B 110.5
H23A C23 H23B 108.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
I1 C1 2.108(7)
O1 C13 1.364(7)
O1 C12 1.394(6)
O2 C13 1.180(8)
O3 C21 1.335(8)
O3 C23 1.435(9)
O4 C21 1.197(8)
N1 C4 1.360(9)
N1 C8 1.367(10)
N1 H1 0.8800
N2 C21 1.360(7)
N2 C12 1.394(7)
N2 C22 1.448(8)
C1 C2 1.375(11)
C1 C6 1.380(9)
C2 C3 1.363(13)
C2 H2 0.9500
C3 C4 1.390(11)
C3 H3 0.9500
C4 C5 1.412(8)
C5 C6 1.393(8)
C5 C7 1.434(8)
C6 H6 0.9500
C7 C8 1.372(8)
C7 C9 1.505(8)
C8 H8 0.9500
C9 C11 1.500(8)
C9 C10 1.525(9)
C9 H9 1.0000
C10 H10A 0.9800
C10 H10B 0.9800
C10 H10C 0.9800
C11 C12 1.326(8)
C11 H11 0.9500
C13 C14 1.506(9)
C14 C15 1.494(10)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.361(9)
C15 C20 1.371(11)
C16 C17 1.372(11)
C16 H16 0.9500
C17 C18 1.360(12)
C17 H17 0.9500
C18 C19 1.326(12)
C18 H18 0.9500
C19 C20 1.383(12)
C19 H19 0.9500
C20 H20 0.9500
C22 C23 1.523(10)
C22 H22A 0.9900
C22 H22B 0.9900
C23 H23A 0.9900
C23 H23B 0.9900
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
C6 C1 C2 C3 -2.2(11)
I1 C1 C2 C3 178.2(6)
C1 C2 C3 C4 -1.7(12)
C8 N1 C4 C3 179.2(7)
C8 N1 C4 C5 -0.2(7)
C2 C3 C4 N1 -175.0(7)
C2 C3 C4 C5 4.3(11)
N1 C4 C5 C6 176.4(5)
C3 C4 C5 C6 -3.1(9)
N1 C4 C5 C7 -0.8(6)
C3 C4 C5 C7 179.8(6)
C2 C1 C6 C5 3.4(9)
I1 C1 C6 C5 -177.0(4)
C4 C5 C6 C1 -0.8(8)
C7 C5 C6 C1 175.5(6)
C6 C5 C7 C8 -175.1(6)
C4 C5 C7 C8 1.5(6)
C6 C5 C7 C9 6.5(9)
C4 C5 C7 C9 -176.9(5)
C4 N1 C8 C7 1.2(7)
C5 C7 C8 N1 -1.6(7)
C9 C7 C8 N1 176.6(6)
C8 C7 C9 C11 -98.2(7)
C5 C7 C9 C11 79.7(7)
C8 C7 C9 C10 24.1(9)
C5 C7 C9 C10 -158.0(6)
C7 C9 C11 C12 -116.2(6)
C10 C9 C11 C12 119.4(7)
C9 C11 C12 N2 -172.7(5)
C9 C11 C12 O1 7.7(8)
C21 N2 C12 C11 -165.2(6)
C22 N2 C12 C11 18.1(9)
C21 N2 C12 O1 14.5(8)
C22 N2 C12 O1 -162.2(5)
C13 O1 C12 C11 -107.4(6)
C13 O1 C12 N2 73.0(6)
C12 O1 C13 O2 3.2(10)
C12 O1 C13 C14 -177.6(6)
O2 C13 C14 C15 -6.5(13)
O1 C13 C14 C15 174.4(7)
C13 C14 C15 C16 118.1(8)
C13 C14 C15 C20 -63.0(11)
C20 C15 C16 C17 -2.4(12)
C14 C15 C16 C17 176.5(8)
C15 C16 C17 C18 -1.0(13)
C16 C17 C18 C19 2.8(15)
C17 C18 C19 C20 -1.0(17)
C16 C15 C20 C19 4.2(15)
C14 C15 C20 C19 -174.7(10)
C18 C19 C20 C15 -2.6(18)
C23 O3 C21 O4 179.6(8)
C23 O3 C21 N2 -0.8(9)
C12 N2 C21 O4 5.7(13)
C22 N2 C21 O4 -177.4(9)
C12 N2 C21 O3 -173.9(5)
C22 N2 C21 O3 3.1(9)
C21 N2 C22 C23 -3.8(8)
C12 N2 C22 C23 173.4(5)
C21 O3 C23 C22 -1.6(9)
N2 C22 C23 O3 3.1(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139183038
