#------------------------------------------------------------------------------
#$Date: 2023-12-12 11:56:26 +0200 (Tue, 12 Dec 2023) $
#$Revision: 288243 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/10/17/4101743.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_4101743
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            'C25 H26 O4'
_chemical_formula_weight         390.46
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 112.992(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.9697(14)
_cell_length_b                   6.1221(7)
_cell_length_c                   14.1396(15)
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      39.18
_cell_measurement_theta_min      2.92
_cell_volume                     1033.5(2)
_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 0.957
_diffrn_measured_fraction_theta_max 0.957
_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  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0457
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21285
_diffrn_reflns_theta_full        39.72
_diffrn_reflns_theta_max         39.72
_diffrn_reflns_theta_min         2.92
_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    0.084
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.978811
_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    1.255
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.506
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         9768
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0389
_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)+(0.0679P)²+0.0273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                9151
_reflns_number_total             9768
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja075794xsi20070809_093227.cif
_cod_data_source_block           cno-854_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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      P2(1)
_cod_database_code               4101743
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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 0.57315(5) 1.14188(13) 0.27911(5) 0.01500(11) Uani 1 1 d . . .
O1 O 0.69909(7) 1.40960(13) 0.39350(5) 0.02726(13) Uani 1 1 d . . .
C2 C 0.59178(6) 1.25591(13) 0.18917(5) 0.01599(11) Uani 1 1 d . . .
H2A H 0.5287(11) 1.205(3) 0.1264(9) 0.014(3) Uiso 1 1 d . . .
H2B H 0.5847(16) 1.409(4) 0.1914(14) 0.041(5) Uiso 1 1 d . . .
O2 O 0.59654(6) 1.19023(16) 0.45115(5) 0.02765(15) Uani 1 1 d . . .
C3 C 0.70431(5) 1.16834(11) 0.19338(5) 0.01254(10) Uani 1 1 d . . .
H3 H 0.7647 1.2663 0.2395 0.015 Uiso 1 1 calc R . .
O3 O 0.39179(6) 0.96804(17) 0.23861(6) 0.03027(16) Uani 1 1 d . . .
C4 C 0.71886(5) 1.14963(11) 0.09044(4) 0.01230(9) Uani 1 1 d . . .
O4 O 0.40895(6) 1.33517(15) 0.25222(6) 0.02934(15) Uani 1 1 d . . .
C5 C 0.83104(5) 1.03438(12) 0.11342(5) 0.01274(10) Uani 1 1 d . . .
C6 C 0.89287(6) 1.07732(13) 0.05390(5) 0.01632(11) Uani 1 1 d . . .
H6 H 0.8655(13) 1.169(3) 0.0009(11) 0.023(3) Uiso 1 1 d . . .
C7 C 0.99371(7) 0.97116(15) 0.07226(6) 0.01960(13) Uani 1 1 d . . .
H7 H 1.0363(12) 1.003(3) 0.0315(11) 0.020(3) Uiso 1 1 d . . .
C8 C 1.03399(6) 0.81874(15) 0.15135(6) 0.01840(12) Uani 1 1 d . . .
H8 H 1.1033 0.7475 0.1645 0.022 Uiso 1 1 calc R . .
C9 C 0.97341(5) 0.76924(12) 0.21176(5) 0.01419(10) Uani 1 1 d . . .
C10 C 0.87028(5) 0.87475(12) 0.19196(5) 0.01246(10) Uani 1 1 d . . .
C11 C 0.79917(5) 0.81278(12) 0.24730(5) 0.01286(10) Uani 1 1 d . . .
H11 H 0.8136(11) 0.678(3) 0.2830(10) 0.020(3) Uiso 1 1 d . . .
C12 C 0.71721(5) 0.94844(11) 0.24536(5) 0.01242(10) Uani 1 1 d . . .
C13 C 0.62720(6) 0.91349(13) 0.28632(6) 0.01580(11) Uani 1 1 d . . .
H13A H 0.6536(13) 0.862(3) 0.3512(12) 0.033(4) Uiso 1 1 d . . .
H13B H 0.5700(13) 0.820(3) 0.2434(11) 0.028(4) Uiso 1 1 d . . .
C14 C 0.71546(6) 1.37884(13) 0.04534(6) 0.01764(12) Uani 1 1 d . . .
H14A H 0.7818 1.4612 0.0890 0.026 Uiso 1 1 calc R . .
H14B H 0.6478 1.4551 0.0423 0.026 Uiso 1 1 calc R . .
H14C H 0.7146 1.3666 -0.0241 0.026 Uiso 1 1 calc R . .
C15 C 0.62651(6) 1.00926(14) 0.01156(5) 0.01730(12) Uani 1 1 d . . .
H15B H 0.6432(12) 0.982(3) -0.0473(12) 0.024(3) Uiso 1 1 d . . .
H15C H 0.6280(16) 0.856(4) 0.0381(14) 0.042(5) Uiso 1 1 d . . .
H15A H 0.5552(14) 1.075(3) -0.0098(13) 0.031(4) Uiso 1 1 d . . .
C16 C 1.02224(5) 0.61125(12) 0.29760(5) 0.01414(10) Uani 1 1 d . . .
C17 C 1.05354(6) 0.40199(13) 0.27945(6) 0.01754(12) Uani 1 1 d . . .
H17 H 1.0383(11) 0.358(3) 0.2103(10) 0.020(3) Uiso 1 1 d . . .
C18 C 1.10377(7) 0.25693(15) 0.36071(7) 0.02046(13) Uani 1 1 d . . .
H18 H 1.1188(18) 0.111(4) 0.3404(16) 0.051(6) Uiso 1 1 d . . .
C19 C 1.12422(7) 0.31985(16) 0.46117(6) 0.02101(13) Uani 1 1 d . . .
H19 H 1.1618(15) 0.220(4) 0.5165(13) 0.037(4) Uiso 1 1 d . . .
C20 C 1.09377(7) 0.52809(15) 0.48000(6) 0.01965(13) Uani 1 1 d . . .
H20 H 1.1034(13) 0.578(3) 0.5496(12) 0.024(3) Uiso 1 1 d . . .
C21 C 1.04261(6) 0.67285(13) 0.39876(5) 0.01656(11) Uani 1 1 d . . .
H21 H 1.0259(11) 0.821(3) 0.4113(10) 0.020(3) Uiso 1 1 d . . .
C22 C 0.63091(7) 1.26670(14) 0.37948(5) 0.01880(12) Uani 1 1 d . . .
C23 C 0.64521(11) 1.2966(3) 0.55066(8) 0.0397(3) Uani 1 1 d . . .
H23A H 0.6057(16) 1.257(4) 0.5902(14) 0.046(5) Uiso 1 1 d . . .
H23B H 0.7273(14) 1.265(3) 0.5869(13) 0.033(4) Uiso 1 1 d . . .
H23C H 0.6303(19) 1.439(5) 0.5455(17) 0.056(6) Uiso 1 1 d . . .
C24 C 0.44821(6) 1.13085(17) 0.25539(5) 0.02009(14) Uani 1 1 d . . .
C25 C 0.29105(10) 1.3542(3) 0.22914(12) 0.0461(4) Uani 1 1 d . . .
H25C H 0.2563(17) 1.292(4) 0.1647(16) 0.047(5) Uiso 1 1 d . . .
H25A H 0.2716(17) 1.277(4) 0.2748(16) 0.047(5) Uiso 1 1 d . . .
H25B H 0.279(2) 1.531(5) 0.2246(18) 0.063(7) 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'
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
C24 C1 C22 108.70(6) . . ?
C24 C1 C13 112.93(7) . . ?
C22 C1 C13 110.21(6) . . ?
C24 C1 C2 109.44(5) . . ?
C22 C1 C2 111.12(7) . . ?
C13 C1 C2 104.41(6) . . ?
C3 C2 C1 105.16(5) . . ?
C22 O2 C23 115.39(10) . . ?
C12 C3 C2 104.66(6) . . ?
C12 C3 C4 111.19(5) . . ?
C2 C3 C4 117.02(5) . . ?
C5 C4 C14 112.32(6) . . ?
C5 C4 C15 107.57(6) . . ?
C14 C4 C15 108.74(5) . . ?
C5 C4 C3 106.84(5) . . ?
C14 C4 C3 109.25(6) . . ?
C15 C4 C3 112.16(6) . . ?
C24 O4 C25 115.99(11) . . ?
C6 C5 C10 119.19(6) . . ?
C6 C5 C4 120.44(6) . . ?
C10 C5 C4 120.29(6) . . ?
C7 C6 C5 121.28(7) . . ?
C6 C7 C8 119.57(7) . . ?
C7 C8 C9 120.73(7) . . ?
C8 C9 C10 119.59(6) . . ?
C8 C9 C16 118.50(6) . . ?
C10 C9 C16 121.89(6) . . ?
C9 C10 C5 119.58(6) . . ?
C9 C10 C11 121.21(6) . . ?
C5 C10 C11 119.10(6) . . ?
C12 C11 C10 119.04(6) . . ?
C11 C12 C13 129.13(7) . . ?
C11 C12 C3 119.86(6) . . ?
C13 C12 C3 110.98(6) . . ?
C12 C13 C1 104.18(6) . . ?
C17 C16 C21 118.80(6) . . ?
C17 C16 C9 120.55(6) . . ?
C21 C16 C9 120.58(6) . . ?
C18 C17 C16 120.52(7) . . ?
C19 C18 C17 120.32(8) . . ?
C20 C19 C18 119.56(7) . . ?
C19 C20 C21 120.23(7) . . ?
C20 C21 C16 120.56(7) . . ?
O1 C22 O2 124.67(8) . . ?
O1 C22 C1 125.39(7) . . ?
O2 C22 C1 109.92(8) . . ?
O3 C24 O4 124.78(7) . . ?
O3 C24 C1 126.36(8) . . ?
O4 C24 C1 108.82(8) . . ?
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 C24 1.5226(10) . ?
C1 C22 1.5260(10) . ?
C1 C13 1.5496(11) . ?
C1 C2 1.5501(10) . ?
O1 C22 1.2040(12) . ?
C2 C3 1.5341(9) . ?
O2 C22 1.3408(11) . ?
O2 C23 1.4520(13) . ?
C3 C12 1.5115(10) . ?
C3 C4 1.5434(9) . ?
O3 C24 1.2040(13) . ?
C4 C5 1.5332(9) . ?
C4 C14 1.5348(10) . ?
C4 C15 1.5406(9) . ?
O4 C24 1.3447(12) . ?
O4 C25 1.4382(13) . ?
C5 C6 1.3956(10) . ?
C5 C10 1.4163(9) . ?
C6 C7 1.3911(11) . ?
C7 C8 1.3921(11) . ?
C8 C9 1.4010(10) . ?
C9 C10 1.4115(9) . ?
C9 C16 1.4864(10) . ?
C10 C11 1.4732(10) . ?
C11 C12 1.3408(10) . ?
C12 C13 1.5074(10) . ?
C16 C17 1.3975(11) . ?
C16 C21 1.4010(10) . ?
C17 C18 1.3958(11) . ?
C18 C19 1.3936(13) . ?
C19 C20 1.3908(14) . ?
C20 C21 1.3964(11) . ?
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
C24 C1 C2 C3 -154.36(7) . . . . ?
C22 C1 C2 C3 85.59(7) . . . . ?
C13 C1 C2 C3 -33.21(7) . . . . ?
C1 C2 C3 C12 25.45(7) . . . . ?
C1 C2 C3 C4 149.01(6) . . . . ?
C12 C3 C4 C5 -53.30(7) . . . . ?
C2 C3 C4 C5 -173.46(6) . . . . ?
C12 C3 C4 C14 -175.03(5) . . . . ?
C2 C3 C4 C14 64.81(8) . . . . ?
C12 C3 C4 C15 64.33(7) . . . . ?
C2 C3 C4 C15 -55.83(8) . . . . ?
C14 C4 C5 C6 -30.80(9) . . . . ?
C15 C4 C5 C6 88.81(8) . . . . ?
C3 C4 C5 C6 -150.57(6) . . . . ?
C14 C4 C5 C10 152.47(6) . . . . ?
C15 C4 C5 C10 -87.92(7) . . . . ?
C3 C4 C5 C10 32.69(8) . . . . ?
C10 C5 C6 C7 -1.92(11) . . . . ?
C4 C5 C6 C7 -178.70(7) . . . . ?
C5 C6 C7 C8 0.10(13) . . . . ?
C6 C7 C8 C9 0.80(13) . . . . ?
C7 C8 C9 C10 0.17(12) . . . . ?
C7 C8 C9 C16 -177.82(7) . . . . ?
C8 C9 C10 C5 -2.00(10) . . . . ?
C16 C9 C10 C5 175.92(6) . . . . ?
C8 C9 C10 C11 174.31(7) . . . . ?
C16 C9 C10 C11 -7.77(10) . . . . ?
C6 C5 C10 C9 2.86(10) . . . . ?
C4 C5 C10 C9 179.63(6) . . . . ?
C6 C5 C10 C11 -173.53(6) . . . . ?
C4 C5 C10 C11 3.24(9) . . . . ?
C9 C10 C11 C12 163.87(6) . . . . ?
C5 C10 C11 C12 -19.80(9) . . . . ?
C10 C11 C12 C13 173.39(6) . . . . ?
C10 C11 C12 C3 -4.37(9) . . . . ?
C2 C3 C12 C11 169.89(6) . . . . ?
C4 C3 C12 C11 42.65(8) . . . . ?
C2 C3 C12 C13 -8.25(7) . . . . ?
C4 C3 C12 C13 -135.48(6) . . . . ?
C11 C12 C13 C1 169.86(7) . . . . ?
C3 C12 C13 C1 -12.22(7) . . . . ?
C24 C1 C13 C12 146.38(6) . . . . ?
C22 C1 C13 C12 -91.83(7) . . . . ?
C2 C1 C13 C12 27.57(7) . . . . ?
C8 C9 C16 C17 -55.54(10) . . . . ?
C10 C9 C16 C17 126.53(7) . . . . ?
C8 C9 C16 C21 121.43(8) . . . . ?
C10 C9 C16 C21 -56.51(10) . . . . ?
C21 C16 C17 C18 0.24(11) . . . . ?
C9 C16 C17 C18 177.25(7) . . . . ?
C16 C17 C18 C19 -0.55(12) . . . . ?
C17 C18 C19 C20 0.29(12) . . . . ?
C18 C19 C20 C21 0.28(12) . . . . ?
C19 C20 C21 C16 -0.59(12) . . . . ?
C17 C16 C21 C20 0.32(11) . . . . ?
C9 C16 C21 C20 -176.69(7) . . . . ?
C23 O2 C22 O1 1.71(14) . . . . ?
C23 O2 C22 C1 -179.75(9) . . . . ?
C24 C1 C22 O1 -133.63(9) . . . . ?
C13 C1 C22 O1 102.10(10) . . . . ?
C2 C1 C22 O1 -13.14(11) . . . . ?
C24 C1 C22 O2 47.84(9) . . . . ?
C13 C1 C22 O2 -76.42(8) . . . . ?
C2 C1 C22 O2 168.33(6) . . . . ?
C25 O4 C24 O3 1.45(13) . . . . ?
C25 O4 C24 C1 179.20(8) . . . . ?
C22 C1 C24 O3 -125.91(9) . . . . ?
C13 C1 C24 O3 -3.28(11) . . . . ?
C2 C1 C24 O3 112.57(9) . . . . ?
C22 C1 C24 O4 56.38(8) . . . . ?
C13 C1 C24 O4 179.02(6) . . . . ?
C2 C1 C24 O4 -65.14(8) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660063
