#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:01:04 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178416 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/37/4023713.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_4023713
loop_
_publ_author_name
'Catelijne H. M. Amijs'
'Verónica López-Carrillo'
'Mihai Raducan'
'Patricia Pérez-Galán'
'Catalina Ferrer'
'Antonio M. Echavarren'
_publ_section_title
;
 Gold(I)-Catalyzed Intermolecular Addition of Carbon
 Nucleophiles to 1,5- and 1,6-Enynes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7721
_journal_page_last               7730
_journal_paper_doi               10.1021/jo8014769
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C26 H23 N O'
_chemical_formula_weight         365.45
_chemical_name_systematic
;
 ?
;
_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                   8.9050(6)
_cell_length_b                   19.1445(13)
_cell_length_c                   22.5916(15)
_cell_measurement_reflns_used    8050
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.28
_cell_measurement_theta_min      3.25
_cell_volume                     3851.5(4)
_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 0.987
_diffrn_measured_fraction_theta_max 0.987
_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  0.0450
_diffrn_reflns_av_sigmaI/netI    0.0377
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            38294
_diffrn_reflns_theta_full        35.41
_diffrn_reflns_theta_max         35.41
_diffrn_reflns_theta_min         2.79
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_current           70
_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    0.076
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9624
_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            white
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         8633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0660
_refine_ls_R_factor_gt           0.0490
_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)+(0.0745P)²+0.7453P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1396
_reflns_number_gt                6667
_reflns_number_total             8633
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8014769_si_001.cif
_cod_data_source_block           v0489_0m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023713
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 0.27907(7) 0.25136(4) 0.18971(3) 0.01795(12) Uani 1 1 d . . .
C1 C 0.15441(9) 0.16562(4) 0.13452(3) 0.01532(14) Uani 1 1 d . . .
H1 H 0.0531 0.1515 0.1196 0.018 Uiso 1 1 calc R . .
N1 N -0.09654(9) 0.29612(4) 0.20174(3) 0.01715(13) Uani 1 1 d . . .
H1N H -0.1185(19) 0.2817(9) 0.2396(7) 0.040(4) Uiso 1 1 d . . .
C2 C 0.22594(9) 0.21739(4) 0.08997(3) 0.01558(14) Uani 1 1 d . . .
H2 H 0.2843 0.1918 0.0590 0.019 Uiso 1 1 calc R . .
C3 C 0.10029(9) 0.26276(4) 0.06124(3) 0.01522(14) Uani 1 1 d . . .
H3 H 0.0358 0.2306 0.0374 0.018 Uiso 1 1 calc R . .
C4 C 0.00390(9) 0.29160(4) 0.11002(3) 0.01513(14) Uani 1 1 d . . .
C5 C -0.12568(9) 0.33594(4) 0.10792(4) 0.01588(14) Uani 1 1 d . . .
C6 C -0.19948(11) 0.37306(4) 0.06276(4) 0.01931(15) Uani 1 1 d . . .
H6 H -0.1569 0.3763 0.0243 0.023 Uiso 1 1 calc R . .
C7 C -0.33542(11) 0.40484(5) 0.07542(5) 0.02272(17) Uani 1 1 d . . .
H7 H -0.3882 0.4284 0.0448 0.027 Uiso 1 1 calc R . .
C8 C -0.39675(11) 0.40283(5) 0.13285(5) 0.02401(18) Uani 1 1 d . . .
H8 H -0.4902 0.4251 0.1402 0.029 Uiso 1 1 calc R . .
C9 C -0.32366(10) 0.36911(5) 0.17873(4) 0.02130(16) Uani 1 1 d . . .
H9 H -0.3642 0.3686 0.2176 0.026 Uiso 1 1 calc R . .
C10 C -0.18817(9) 0.33581(4) 0.16573(4) 0.01678(14) Uani 1 1 d . . .
C11 C 0.01673(9) 0.26838(4) 0.16726(3) 0.01513(13) Uani 1 1 d . . .
C12 C 0.13392(9) 0.21681(4) 0.18741(3) 0.01552(14) Uani 1 1 d . . .
C13 C 0.24343(10) 0.10039(4) 0.14923(4) 0.01673(14) Uani 1 1 d . . .
C14 C 0.39363(10) 0.09042(5) 0.13420(4) 0.02152(16) Uani 1 1 d . . .
H14 H 0.4455 0.1257 0.1129 0.026 Uiso 1 1 calc R . .
C15 C 0.46901(11) 0.02928(5) 0.15004(5) 0.02544(18) Uani 1 1 d . . .
H15 H 0.5710 0.0231 0.1389 0.031 Uiso 1 1 calc R . .
C16 C 0.39611(11) -0.02259(5) 0.18193(4) 0.02358(18) Uani 1 1 d . . .
H16 H 0.4483 -0.0637 0.1934 0.028 Uiso 1 1 calc R . .
C17 C 0.24609(11) -0.01374(5) 0.19681(5) 0.02433(18) Uani 1 1 d . . .
H17 H 0.1950 -0.0490 0.2185 0.029 Uiso 1 1 calc R . .
C18 C 0.17030(10) 0.04666(5) 0.18004(4) 0.02191(17) Uani 1 1 d . . .
H18 H 0.0670 0.0516 0.1897 0.026 Uiso 1 1 calc R . .
C19 C 0.10394(10) 0.18686(5) 0.24834(4) 0.01999(16) Uani 1 1 d . . .
H19A H 0.1846 0.1543 0.2589 0.030 Uiso 1 1 calc R . .
H19B H 0.0077 0.1620 0.2481 0.030 Uiso 1 1 calc R . .
H19C H 0.1001 0.2249 0.2774 0.030 Uiso 1 1 calc R . .
C20 C 0.16239(10) 0.31719(4) 0.01905(4) 0.01616(14) Uani 1 1 d . . .
C21 C 0.18914(10) 0.29877(4) -0.03981(4) 0.01675(14) Uani 1 1 d . . .
H21 H 0.1645 0.2531 -0.0531 0.020 Uiso 1 1 calc R . .
C22 C 0.25150(11) 0.34643(5) -0.07939(4) 0.02061(16) Uani 1 1 d . . .
H22 H 0.2699 0.3331 -0.1192 0.025 Uiso 1 1 calc R . .
C23 C 0.28669(11) 0.41352(5) -0.06054(4) 0.02361(18) Uani 1 1 d . . .
H23 H 0.3308 0.4459 -0.0872 0.028 Uiso 1 1 calc R . .
C24 C 0.25707(13) 0.43301(5) -0.00252(5) 0.0269(2) Uani 1 1 d . . .
H24 H 0.2793 0.4791 0.0103 0.032 Uiso 1 1 calc R . .
C25 C 0.19486(12) 0.38524(5) 0.03705(4) 0.02345(18) Uani 1 1 d . . .
H25 H 0.1744 0.3991 0.0766 0.028 Uiso 1 1 calc R . .
C26 C 0.33108(10) 0.26092(5) 0.12950(4) 0.01824(15) Uani 1 1 d . . .
H26A H 0.4361 0.2446 0.1254 0.022 Uiso 1 1 calc R . .
H26B H 0.3265 0.3109 0.1183 0.022 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'
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
C26 O1 C12 107.96(6) . . ?
C13 C1 C2 117.02(7) . . ?
C13 C1 C12 114.31(7) . . ?
C2 C1 C12 98.29(6) . . ?
C10 N1 C11 108.14(7) . . ?
C26 C2 C1 102.69(6) . . ?
C26 C2 C3 112.13(7) . . ?
C1 C2 C3 109.39(7) . . ?
C4 C3 C20 114.64(7) . . ?
C4 C3 C2 108.04(6) . . ?
C20 C3 C2 112.52(7) . . ?
C11 C4 C5 106.85(7) . . ?
C11 C4 C3 121.65(7) . . ?
C5 C4 C3 130.82(7) . . ?
C6 C5 C10 119.02(8) . . ?
C6 C5 C4 134.37(8) . . ?
C10 C5 C4 106.52(7) . . ?
C7 C6 C5 118.73(8) . . ?
C6 C7 C8 121.16(9) . . ?
C9 C8 C7 121.36(9) . . ?
C8 C9 C10 117.52(9) . . ?
N1 C10 C9 129.68(8) . . ?
N1 C10 C5 108.14(7) . . ?
C9 C10 C5 122.11(8) . . ?
C4 C11 N1 110.25(7) . . ?
C4 C11 C12 123.67(7) . . ?
N1 C11 C12 125.99(7) . . ?
O1 C12 C11 109.19(7) . . ?
O1 C12 C19 107.24(7) . . ?
C11 C12 C19 113.60(7) . . ?
O1 C12 C1 102.12(6) . . ?
C11 C12 C1 105.18(6) . . ?
C19 C12 C1 118.70(7) . . ?
C14 C13 C18 117.80(8) . . ?
C14 C13 C1 124.16(8) . . ?
C18 C13 C1 118.05(8) . . ?
C13 C14 C15 120.94(9) . . ?
C16 C15 C14 120.53(9) . . ?
C15 C16 C17 119.25(9) . . ?
C16 C17 C18 120.15(9) . . ?
C17 C18 C13 121.30(9) . . ?
C25 C20 C21 118.56(8) . . ?
C25 C20 C3 122.28(7) . . ?
C21 C20 C3 119.16(7) . . ?
C22 C21 C20 120.93(8) . . ?
C23 C22 C21 119.92(8) . . ?
C24 C23 C22 119.68(8) . . ?
C23 C24 C25 120.32(9) . . ?
C24 C25 C20 120.55(9) . . ?
O1 C26 C2 106.38(6) . . ?
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
O1 C26 1.4485(10) . ?
O1 C12 1.4529(10) . ?
C1 C13 1.5161(12) . ?
C1 C2 1.5494(11) . ?
C1 C12 1.5559(11) . ?
N1 C10 1.3801(11) . ?
N1 C11 1.3806(11) . ?
C2 C26 1.5390(12) . ?
C2 C3 1.5581(12) . ?
C3 C4 1.5019(11) . ?
C3 C20 1.5166(11) . ?
C4 C11 1.3724(11) . ?
C4 C5 1.4332(12) . ?
C5 C6 1.4066(12) . ?
C5 C10 1.4196(12) . ?
C6 C7 1.3847(13) . ?
C7 C8 1.4082(15) . ?
C8 C9 1.3838(14) . ?
C9 C10 1.3958(12) . ?
C11 C12 1.5070(12) . ?
C12 C19 1.5150(12) . ?
C13 C14 1.3931(13) . ?
C13 C18 1.4023(12) . ?
C14 C15 1.3960(13) . ?
C15 C16 1.3880(14) . ?
C16 C17 1.3880(14) . ?
C17 C18 1.3915(13) . ?
C20 C25 1.3950(12) . ?
C20 C21 1.3963(11) . ?
C21 C22 1.3930(12) . ?
C22 C23 1.3890(14) . ?
C23 C24 1.3881(14) . ?
C24 C25 1.3936(13) . ?
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 C26 -83.46(8) . . . . ?
C12 C1 C2 C26 39.31(7) . . . . ?
C13 C1 C2 C3 157.30(7) . . . . ?
C12 C1 C2 C3 -79.93(7) . . . . ?
C26 C2 C3 C4 -63.44(8) . . . . ?
C1 C2 C3 C4 49.78(8) . . . . ?
C26 C2 C3 C20 64.12(9) . . . . ?
C1 C2 C3 C20 177.35(6) . . . . ?
C20 C3 C4 C11 -136.99(8) . . . . ?
C2 C3 C4 C11 -10.65(10) . . . . ?
C20 C3 C4 C5 53.78(12) . . . . ?
C2 C3 C4 C5 -179.89(8) . . . . ?
C11 C4 C5 C6 -177.72(9) . . . . ?
C3 C4 C5 C6 -7.28(16) . . . . ?
C11 C4 C5 C10 -1.32(9) . . . . ?
C3 C4 C5 C10 169.11(8) . . . . ?
C10 C5 C6 C7 -3.78(12) . . . . ?
C4 C5 C6 C7 172.27(9) . . . . ?
C5 C6 C7 C8 2.59(13) . . . . ?
C6 C7 C8 C9 0.01(15) . . . . ?
C7 C8 C9 C10 -1.33(14) . . . . ?
C11 N1 C10 C9 173.82(9) . . . . ?
C11 N1 C10 C5 -3.25(9) . . . . ?
C8 C9 C10 N1 -176.67(9) . . . . ?
C8 C9 C10 C5 0.04(13) . . . . ?
C6 C5 C10 N1 179.87(7) . . . . ?
C4 C5 C10 N1 2.82(9) . . . . ?
C6 C5 C10 C9 2.53(12) . . . . ?
C4 C5 C10 C9 -174.52(8) . . . . ?
C5 C4 C11 N1 -0.66(9) . . . . ?
C3 C4 C11 N1 -172.17(7) . . . . ?
C5 C4 C11 C12 176.24(7) . . . . ?
C3 C4 C11 C12 4.73(12) . . . . ?
C10 N1 C11 C4 2.46(9) . . . . ?
C10 N1 C11 C12 -174.35(8) . . . . ?
C26 O1 C12 C11 -74.09(8) . . . . ?
C26 O1 C12 C19 162.42(7) . . . . ?
C26 O1 C12 C1 36.91(8) . . . . ?
C4 C11 C12 O1 73.60(10) . . . . ?
N1 C11 C12 O1 -110.00(9) . . . . ?
C4 C11 C12 C19 -166.76(8) . . . . ?
N1 C11 C12 C19 9.64(12) . . . . ?
C4 C11 C12 C1 -35.35(10) . . . . ?
N1 C11 C12 C1 141.05(8) . . . . ?
C13 C1 C12 O1 78.05(8) . . . . ?
C2 C1 C12 O1 -46.67(7) . . . . ?
C13 C1 C12 C11 -167.96(7) . . . . ?
C2 C1 C12 C11 67.32(7) . . . . ?
C13 C1 C12 C19 -39.54(10) . . . . ?
C2 C1 C12 C19 -164.26(7) . . . . ?
C2 C1 C13 C14 12.22(12) . . . . ?
C12 C1 C13 C14 -101.85(10) . . . . ?
C2 C1 C13 C18 -167.93(8) . . . . ?
C12 C1 C13 C18 78.00(10) . . . . ?
C18 C13 C14 C15 -0.82(14) . . . . ?
C1 C13 C14 C15 179.03(9) . . . . ?
C13 C14 C15 C16 -0.91(16) . . . . ?
C14 C15 C16 C17 1.43(16) . . . . ?
C15 C16 C17 C18 -0.23(15) . . . . ?
C16 C17 C18 C13 -1.54(15) . . . . ?
C14 C13 C18 C17 2.04(14) . . . . ?
C1 C13 C18 C17 -177.82(9) . . . . ?
C4 C3 C20 C25 30.62(12) . . . . ?
C2 C3 C20 C25 -93.36(10) . . . . ?
C4 C3 C20 C21 -149.79(8) . . . . ?
C2 C3 C20 C21 86.22(9) . . . . ?
C25 C20 C21 C22 2.09(13) . . . . ?
C3 C20 C21 C22 -177.51(8) . . . . ?
C20 C21 C22 C23 -0.57(14) . . . . ?
C21 C22 C23 C24 -1.08(15) . . . . ?
C22 C23 C24 C25 1.17(16) . . . . ?
C23 C24 C25 C20 0.39(17) . . . . ?
C21 C20 C25 C24 -2.00(15) . . . . ?
C3 C20 C25 C24 177.59(9) . . . . ?
C12 O1 C26 C2 -11.15(9) . . . . ?
C1 C2 C26 O1 -19.17(9) . . . . ?
C3 C2 C26 O1 98.14(8) . . . . ?
