#------------------------------------------------------------------------------
#$Date: 2023-12-12 11:56:26 +0200 (Tue, 12 Dec 2023) $
#$Revision: 288243 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/17/4101742.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_4101742
loop_
_publ_author_name
'Nieto-Oberhuber, Cristina'
'Pérez-Galán, Patricia'
'Herrero-Gómez, Elena'
'Lauterbach, Thorsten'
'Rodríguez, Cristina'
'López, Salomé'
'Bour, Christophe'
'Rosellón, Antonio'
'Cárdenas, Diego J.'
'Echavarren, Antonio M.'
_publ_section_title
;
 Gold(I)-Catalyzed Intramolecular [4+2] Cycloadditions of Arylalkynes or
 1,3-Enynes with Alkenes:  Scope and Mechanism
;
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              269
_journal_page_last               279
_journal_paper_doi               10.1021/ja075794x
_journal_volume                  130
_journal_year                    2008
_chemical_formula_sum            'C19 H21 N O6'
_chemical_formula_weight         359.37
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                81.193(5)
_cell_angle_beta                 75.297(5)
_cell_angle_gamma                85.650(5)
_cell_formula_units_Z            2
_cell_length_a                   6.8152(11)
_cell_length_b                   10.669(2)
_cell_length_c                   12.389(2)
_cell_measurement_reflns_used    1505
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.66
_cell_measurement_theta_min      2.76
_cell_volume                     860.4(3)
_computing_cell_refinement       'Bruker-Nonius Apex v1.0-22 2002'
_computing_data_collection       'Bruker-Nonius Apex v1.0-22 2002'
_computing_data_reduction        'SAINT+ Version 7.06A Bruker-Nonius, 2004'
_computing_molecular_graphics    'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_publication_material  'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'Shelxtl Version 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'Shelxtl Version 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 0.580
_diffrn_measured_fraction_theta_max 0.580
_diffrn_measurement_device_type  'Kappa 4-axis goniometer bruker-nonius'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support
'magnetic support whith 10 micron nylon fiber cryoloop'
_diffrn_radiation_monochromator  'Multilayer Montel 200 mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            5572
_diffrn_reflns_theta_full        32.77
_diffrn_reflns_theta_max         32.77
_diffrn_reflns_theta_min         2.76
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           90
_diffrn_source_power             50
_diffrn_source_size              '3 mm x 0.3 mm fine focus'
_diffrn_source_type              'Bruker-Nonius FR 591'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.947811
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2.1 2003 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            translucent
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     315
_refine_ls_number_reflns         3694
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1077
_refine_ls_R_factor_gt           0.0744
_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)+(0.1712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2096
_refine_ls_wR_factor_ref         0.2390
_reflns_number_gt                2499
_reflns_number_total             3694
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja075794xsi20070809_093159.cif
_cod_data_source_block           cno853_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1673 2011-04-08 12:14:43Z adriana 

The following automatic conversions were performed:

data name '_diffrn_measurement_specimen_suppport' was replaced with
'_diffrn_measurement_specimen_support' as specified in the
replacement file 'data/replacement-values/replacement_tags.lst'.

Automatic conversion script
Id: cif_correct_tags 9268 2022-04-12 08:56:07Z antanas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4101742
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.3282(4) 0.3411(3) 0.86855(19) 0.0140(6) Uani 1 1 d . . .
N1 N 0.2447(4) 1.0859(3) 0.51179(19) 0.0209(7) Uani 1 1 d . . .
O1 O 0.2252(4) 1.0570(2) 0.42249(16) 0.0249(6) Uani 1 1 d . . .
C2 C 0.2409(5) 0.3912(3) 0.7654(2) 0.0160(6) Uani 1 1 d . . .
H2A H 0.293(7) 0.345(5) 0.706(3) 0.027(9) Uiso 1 1 d . . .
H2B H 0.105(6) 0.376(4) 0.789(3) 0.020(8) Uiso 1 1 d . . .
O2 O 0.2512(4) 1.1954(2) 0.52877(18) 0.0294(6) Uani 1 1 d . . .
C3 C 0.3001(4) 0.5313(3) 0.7400(2) 0.0162(6) Uani 1 1 d . . .
H3 H 0.4468 0.5335 0.6990 0.019 Uiso 1 1 calc R . .
O3 O 0.6828(3) 0.3754(2) 0.85310(16) 0.0220(6) Uani 1 1 d . . .
C4 C 0.1813(5) 0.6262(3) 0.6697(2) 0.0189(7) Uani 1 1 d . . .
O4 O 0.6032(3) 0.2231(2) 0.76595(15) 0.0185(5) Uani 1 1 d . . .
C5 C 0.2372(4) 0.7598(3) 0.6764(2) 0.0171(7) Uani 1 1 d . . .
O5 O 0.0906(4) 0.1696(2) 0.92227(17) 0.0263(6) Uani 1 1 d . . .
O6 O 0.3316(3) 0.1750(2) 1.01611(17) 0.0269(7) Uani 1 1 d . . .
C6 C 0.2318(4) 0.8596(3) 0.5895(2) 0.0166(7) Uani 1 1 d . . .
H6 H 0.188(7) 0.851(5) 0.521(3) 0.031(10) Uiso 1 1 d . . .
C7 C 0.2609(4) 0.9821(3) 0.6032(2) 0.0181(7) Uani 1 1 d . . .
C8 C 0.2960(5) 1.0134(3) 0.7011(2) 0.0202(7) Uani 1 1 d . . .
H8 H 0.310(7) 1.092(5) 0.711(3) 0.033(10) Uiso 1 1 d . . .
C9 C 0.3026(5) 0.9141(3) 0.7874(2) 0.0215(7) Uani 1 1 d . . .
H9 H 0.323(6) 0.941(4) 0.861(3) 0.027(9) Uiso 1 1 d . . .
C10 C 0.2724(4) 0.7900(3) 0.7777(2) 0.0164(7) Uani 1 1 d . . .
C11 C 0.2737(4) 0.6877(3) 0.8727(2) 0.0184(7) Uani 1 1 d . . .
H11 H 0.268(6) 0.716(4) 0.945(2) 0.015(7) Uiso 1 1 d . . .
C12 C 0.2826(4) 0.5677(3) 0.85589(19) 0.0161(6) Uani 1 1 d . . .
C13 C 0.2781(4) 0.4483(3) 0.9408(2) 0.0163(6) Uani 1 1 d . . .
H13 H 0.382(6) 0.447(4) 0.992(3) 0.020(8) Uiso 1 1 d . . .
H13B H 0.127(6) 0.435(4) 0.992(3) 0.032(9) Uiso 1 1 d . . .
C14 C -0.0500(5) 0.6190(3) 0.7172(3) 0.0260(9) Uani 1 1 d . . .
H14A H -0.100(6) 0.537(4) 0.708(2) 0.020(8) Uiso 1 1 d . . .
H14B H -0.108(6) 0.670(4) 0.668(3) 0.027(9) Uiso 1 1 d . . .
H14C H -0.079(6) 0.628(4) 0.797(3) 0.023(9) Uiso 1 1 d . . .
C15 C 0.2353(6) 0.5947(3) 0.5482(2) 0.0302(9) Uani 1 1 d . . .
H15B H 0.382(8) 0.618(5) 0.511(3) 0.045(11) Uiso 1 1 d . . .
H15A H 0.210(6) 0.504(4) 0.547(3) 0.023(8) Uiso 1 1 d . . .
H15C H 0.120(9) 0.650(6) 0.509(4) 0.065(15) Uiso 1 1 d . . .
C16 C 0.5582(4) 0.3167(3) 0.83023(19) 0.0131(6) Uani 1 1 d . . .
C17 C 0.8178(5) 0.1949(3) 0.7236(2) 0.0203(7) Uani 1 1 d . . .
H17A H 0.884(6) 0.179(4) 0.784(3) 0.021(8) Uiso 1 1 d . . .
H17B H 0.820(6) 0.121(5) 0.678(3) 0.031(9) Uiso 1 1 d . . .
H17C H 0.882(6) 0.264(4) 0.673(3) 0.020(8) Uiso 1 1 d . . .
C18 C 0.2332(4) 0.2182(3) 0.9357(2) 0.0158(7) Uani 1 1 d . . .
C19 C 0.2495(5) 0.0641(4) 1.0939(3) 0.0281(9) Uani 1 1 d . . .
H19A H 0.111(10) 0.084(7) 1.127(4) 0.070(17) Uiso 1 1 d . . .
H19B H 0.284(8) 0.070(5) 1.158(4) 0.050(13) Uiso 1 1 d . . .
H19C H 0.225(9) 0.011(6) 1.055(4) 0.061(16) 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'
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
C13 C1 C16 111.0(2) . . ?
C13 C1 C18 110.2(2) . . ?
C16 C1 C18 108.4(2) . . ?
C13 C1 C2 103.9(2) . . ?
C16 C1 C2 110.1(2) . . ?
C18 C1 C2 113.2(2) . . ?
O2 N1 O1 123.7(2) . . ?
O2 N1 C7 118.4(2) . . ?
O1 N1 C7 117.9(3) . . ?
C3 C2 C1 102.3(2) . . ?
C12 C3 C2 103.45(19) . . ?
C12 C3 C4 112.3(3) . . ?
C2 C3 C4 118.1(2) . . ?
C5 C4 C15 112.7(2) . . ?
C5 C4 C14 106.9(3) . . ?
C15 C4 C14 108.6(3) . . ?
C5 C4 C3 107.9(2) . . ?
C15 C4 C3 108.6(3) . . ?
C14 C4 C3 112.18(19) . . ?
C16 O4 C17 115.3(2) . . ?
C6 C5 C10 117.7(3) . . ?
C6 C5 C4 121.6(2) . . ?
C10 C5 C4 120.29(18) . . ?
C18 O6 C19 116.2(2) . . ?
C7 C6 C5 120.2(3) . . ?
C6 C7 C8 123.0(2) . . ?
C6 C7 N1 118.7(2) . . ?
C8 C7 N1 118.2(3) . . ?
C7 C8 C9 116.9(3) . . ?
C10 C9 C8 122.1(3) . . ?
C9 C10 C5 120.1(2) . . ?
C9 C10 C11 120.5(2) . . ?
C5 C10 C11 119.3(3) . . ?
C12 C11 C10 119.7(2) . . ?
C11 C12 C3 121.70(19) . . ?
C11 C12 C13 128.8(2) . . ?
C3 C12 C13 109.5(2) . . ?
C12 C13 C1 104.0(2) . . ?
O3 C16 O4 124.3(3) . . ?
O3 C16 C1 124.5(3) . . ?
O4 C16 C1 111.2(2) . . ?
O5 C18 O6 124.6(2) . . ?
O5 C18 C1 126.24(18) . . ?
O6 C18 C1 109.1(2) . . ?
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
C1 C13 1.525(5) . ?
C1 C16 1.532(4) . ?
C1 C18 1.533(3) . ?
C1 C2 1.549(3) . ?
N1 O2 1.224(4) . ?
N1 O1 1.234(3) . ?
N1 C7 1.477(3) . ?
C2 C3 1.543(4) . ?
C3 C12 1.517(4) . ?
C3 C4 1.550(3) . ?
O3 C16 1.205(3) . ?
C4 C5 1.523(4) . ?
C4 C15 1.539(4) . ?
C4 C14 1.540(4) . ?
O4 C16 1.341(4) . ?
O4 C17 1.448(4) . ?
C5 C6 1.399(3) . ?
C5 C10 1.423(4) . ?
O5 C18 1.194(3) . ?
O6 C18 1.344(2) . ?
O6 C19 1.455(3) . ?
C6 C7 1.379(4) . ?
C7 C8 1.387(4) . ?
C8 C9 1.392(3) . ?
C9 C10 1.383(4) . ?
C10 C11 1.479(3) . ?
C11 C12 1.323(4) . ?
C12 C13 1.519(3) . ?
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
C13 C1 C2 C3 41.3(3) . . . . ?
C16 C1 C2 C3 -77.6(3) . . . . ?
C18 C1 C2 C3 160.9(3) . . . . ?
C1 C2 C3 C12 -35.0(3) . . . . ?
C1 C2 C3 C4 -159.7(3) . . . . ?
C12 C3 C4 C5 48.5(3) . . . . ?
C2 C3 C4 C5 168.8(3) . . . . ?
C12 C3 C4 C15 170.9(2) . . . . ?
C2 C3 C4 C15 -68.8(3) . . . . ?
C12 C3 C4 C14 -69.0(3) . . . . ?
C2 C3 C4 C14 51.2(4) . . . . ?
C15 C4 C5 C6 31.9(4) . . . . ?
C14 C4 C5 C6 -87.4(3) . . . . ?
C3 C4 C5 C6 151.7(3) . . . . ?
C15 C4 C5 C10 -156.0(3) . . . . ?
C14 C4 C5 C10 84.8(3) . . . . ?
C3 C4 C5 C10 -36.1(4) . . . . ?
C10 C5 C6 C7 0.3(4) . . . . ?
C4 C5 C6 C7 172.7(3) . . . . ?
C5 C6 C7 C8 -0.1(5) . . . . ?
C5 C6 C7 N1 -177.2(3) . . . . ?
O2 N1 C7 C6 173.0(3) . . . . ?
O1 N1 C7 C6 -6.8(4) . . . . ?
O2 N1 C7 C8 -4.2(4) . . . . ?
O1 N1 C7 C8 175.9(3) . . . . ?
C6 C7 C8 C9 0.5(5) . . . . ?
N1 C7 C8 C9 177.6(3) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C8 C9 C10 C5 1.3(5) . . . . ?
C8 C9 C10 C11 -177.9(3) . . . . ?
C6 C5 C10 C9 -0.9(4) . . . . ?
C4 C5 C10 C9 -173.4(3) . . . . ?
C6 C5 C10 C11 178.3(3) . . . . ?
C4 C5 C10 C11 5.9(4) . . . . ?
C9 C10 C11 C12 -167.4(3) . . . . ?
C5 C10 C11 C12 13.3(4) . . . . ?
C10 C11 C12 C3 2.5(4) . . . . ?
C10 C11 C12 C13 -177.6(3) . . . . ?
C2 C3 C12 C11 -163.5(3) . . . . ?
C4 C3 C12 C11 -35.1(4) . . . . ?
C2 C3 C12 C13 16.6(3) . . . . ?
C4 C3 C12 C13 145.0(2) . . . . ?
C11 C12 C13 C1 -171.0(3) . . . . ?
C3 C12 C13 C1 9.0(3) . . . . ?
C16 C1 C13 C12 87.4(2) . . . . ?
C18 C1 C13 C12 -152.5(2) . . . . ?
C2 C1 C13 C12 -30.9(3) . . . . ?
C17 O4 C16 O3 0.0(3) . . . . ?
C17 O4 C16 C1 178.75(16) . . . . ?
C13 C1 C16 O3 -0.8(3) . . . . ?
C18 C1 C16 O3 -122.0(2) . . . . ?
C2 C1 C16 O3 113.7(3) . . . . ?
C13 C1 C16 O4 -179.54(15) . . . . ?
C18 C1 C16 O4 59.3(2) . . . . ?
C2 C1 C16 O4 -65.0(2) . . . . ?
C19 O6 C18 O5 -2.8(5) . . . . ?
C19 O6 C18 C1 175.1(3) . . . . ?
C13 C1 C18 O5 107.6(4) . . . . ?
C16 C1 C18 O5 -130.8(3) . . . . ?
C2 C1 C18 O5 -8.4(5) . . . . ?
C13 C1 C18 O6 -70.3(3) . . . . ?
C16 C1 C18 O6 51.4(3) . . . . ?
C2 C1 C18 O6 173.8(3) . . . . ?
