#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:03:23 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180329 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/43/7154340.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_7154340
loop_
_publ_author_name
'Handa, Sachin'
'Subramanium, Sri S.'
'Ruch, Aaron A.'
'Tanski, Joseph M.'
'Slaughter, LeGrande M'
_publ_section_title
;
 Ligand- and Brønsted acid/base-switchable reaction pathways in
 gold(i)-catalyzed cycloisomerizations of allenoic acids.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3936
_journal_page_last               3949
_journal_paper_doi               10.1039/c4ob02640c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_moiety         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42
_chemical_melting_point          368.5(15)
_chemical_name_systematic
5-(cyclohexylidenemethyl)-3,3-diphenyldihydrofuran-2(3H)-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2014-04-14 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.1728(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.28820(10)
_cell_length_b                   10.08340(10)
_cell_length_c                   17.6278(2)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      68.75
_cell_measurement_theta_min      5.07
_cell_volume                     1799.96(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (XP)'
_computing_publication_material  'Bruker SHELXTL (XCIF)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_detector_area_resol_mean 0.75
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            26227
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         4.366
_diffrn_standards_decay_%        N/A
_diffrn_standards_interval_count N/A
_diffrn_standards_interval_time  N/A
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.865
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method
'slow diff of pentane into ether/dichloromethane soln'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0029(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0345
_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)+(0.0348P)²+0.7764P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0841
_refine_ls_wR_factor_ref         0.0844
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3122
_reflns_number_total             3169
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob02640c2.cif
_cod_data_source_block           cmpd2a_sh009
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '367-370' was changed to '368.5(15)'
- the average value was taken and precision was estimated.

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 7154340--7154342.cif.
;
_cod_database_code               7154340
#BEGIN Tags that were not found in dictionaries:
_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   0.796
_shelx_estimated_absorpt_t_max   0.865
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.96731(8) 0.41437(8) 0.33833(5) 0.0250(2) Uani 1 1 d . .
C2 C 0.87425(11) 0.42403(11) 0.27439(6) 0.0203(2) Uani 1 1 d . .
O2 O 0.86556(8) 0.52105(8) 0.23419(5) 0.0271(2) Uani 1 1 d . .
C3 C 0.78677(10) 0.29920(11) 0.26454(6) 0.0185(2) Uani 1 1 d . .
C4 C 0.87716(11) 0.20106(11) 0.31577(6) 0.0209(3) Uani 1 1 d . .
H4A H 0.8247 0.1334 0.3377 0.025 Uiso 1 1 calc R U
H4B H 0.9376 0.1559 0.2862 0.025 Uiso 1 1 calc R U
C5 C 0.95365(11) 0.28798(12) 0.37891(7) 0.0227(3) Uani 1 1 d . .
H5 H 0.9013 0.3019 0.4210 0.027 Uiso 1 1 calc R U
C6 C 1.08790(11) 0.23616(12) 0.41152(7) 0.0239(3) Uani 1 1 d . .
H6 H 1.1337 0.1917 0.3767 0.029 Uiso 1 1 calc R U
C7 C 1.15013(11) 0.24578(12) 0.48431(7) 0.0231(3) Uani 1 1 d . .
C8 C 1.09945(13) 0.31396(13) 0.54927(7) 0.0294(3) Uani 1 1 d . .
H8A H 1.0078 0.3444 0.5309 0.035 Uiso 1 1 calc R U
H8B H 1.1545 0.3929 0.5656 0.035 Uiso 1 1 calc R U
C9 C 1.10211(13) 0.22116(14) 0.61848(7) 0.0333(3) Uani 1 1 d . .
H9A H 1.0775 0.2717 0.6620 0.040 Uiso 1 1 calc R U
H9B H 1.0362 0.1497 0.6045 0.040 Uiso 1 1 calc R U
C10 C 1.23837(14) 0.15988(13) 0.64361(7) 0.0312(3) Uani 1 1 d . .
H10A H 1.3023 0.2304 0.6635 0.037 Uiso 1 1 calc R U
H10B H 1.2352 0.0960 0.6859 0.037 Uiso 1 1 calc R U
C11 C 1.28474(13) 0.08895(13) 0.57691(7) 0.0293(3) Uani 1 1 d . .
H11A H 1.2259 0.0128 0.5603 0.035 Uiso 1 1 calc R U
H11B H 1.3752 0.0543 0.5942 0.035 Uiso 1 1 calc R U
C12 C 1.28419(12) 0.18331(13) 0.50884(7) 0.0272(3) Uani 1 1 d . .
H12A H 1.3509 0.2537 0.5237 0.033 Uiso 1 1 calc R U
H12B H 1.3086 0.1337 0.4650 0.033 Uiso 1 1 calc R U
C13 C 0.65988(10) 0.32606(11) 0.29716(6) 0.0181(2) Uani 1 1 d . .
C14 C 0.57368(11) 0.22006(12) 0.30091(6) 0.0217(2) Uani 1 1 d . .
H14 H 0.5958 0.1343 0.2848 0.026 Uiso 1 1 calc R U
C15 C 0.45637(11) 0.23872(12) 0.32782(7) 0.0248(3) Uani 1 1 d . .
H15 H 0.3982 0.1660 0.3295 0.030 Uiso 1 1 calc R U
C16 C 0.42346(11) 0.36319(13) 0.35232(7) 0.0251(3) Uani 1 1 d . .
H16 H 0.3433 0.3757 0.3711 0.030 Uiso 1 1 calc R U
C17 C 0.50797(12) 0.46866(12) 0.34919(7) 0.0242(3) Uani 1 1 d . .
H17 H 0.4860 0.5539 0.3661 0.029 Uiso 1 1 calc R U
C18 C 0.62540(11) 0.45053(11) 0.32125(6) 0.0210(2) Uani 1 1 d . .
H18 H 0.6824 0.5239 0.3187 0.025 Uiso 1 1 calc R U
C19 C 0.75049(10) 0.26201(11) 0.17919(6) 0.0188(2) Uani 1 1 d . .
C20 C 0.79419(11) 0.14608(12) 0.14937(7) 0.0223(3) Uani 1 1 d . .
H20 H 0.8479 0.0858 0.1826 0.027 Uiso 1 1 calc R U
C21 C 0.75974(12) 0.11756(13) 0.07100(7) 0.0265(3) Uani 1 1 d . .
H21 H 0.7898 0.0377 0.0513 0.032 Uiso 1 1 calc R U
C22 C 0.68233(12) 0.20432(13) 0.02184(7) 0.0281(3) Uani 1 1 d . .
H22 H 0.6600 0.1850 -0.0316 0.034 Uiso 1 1 calc R U
C23 C 0.63746(12) 0.31971(13) 0.05117(7) 0.0277(3) Uani 1 1 d . .
H23 H 0.5839 0.3797 0.0177 0.033 Uiso 1 1 calc R U
C24 C 0.67037(11) 0.34798(12) 0.12918(7) 0.0243(3) Uani 1 1 d . .
H24 H 0.6381 0.4267 0.1489 0.029 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 0.0181 0.0091 '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 0.0492 0.0322 '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
C2 O1 C5 110.63(8)
O2 C2 O1 121.32(10)
O2 C2 C3 128.16(10)
O1 C2 C3 110.50(9)
C19 C3 C4 115.89(9)
C19 C3 C2 110.32(9)
C4 C3 C2 100.32(8)
C19 C3 C13 109.53(8)
C4 C3 C13 111.01(9)
C2 C3 C13 109.35(9)
C5 C4 C3 103.88(9)
C5 C4 H4A 111.0
C3 C4 H4A 111.0
C5 C4 H4B 111.0
C3 C4 H4B 111.0
H4A C4 H4B 109.0
O1 C5 C6 109.08(9)
O1 C5 C4 102.91(8)
C6 C5 C4 113.80(10)
O1 C5 H5 110.3
C6 C5 H5 110.3
C4 C5 H5 110.3
C7 C6 C5 126.84(11)
C7 C6 H6 116.6
C5 C6 H6 116.6
C6 C7 C8 126.41(11)
C6 C7 C12 120.34(11)
C8 C7 C12 113.24(10)
C7 C8 C9 111.50(10)
C7 C8 H8A 109.3
C9 C8 H8A 109.3
C7 C8 H8B 109.3
C9 C8 H8B 109.3
H8A C8 H8B 108.0
C10 C9 C8 111.40(11)
C10 C9 H9A 109.3
C8 C9 H9A 109.3
C10 C9 H9B 109.3
C8 C9 H9B 109.3
H9A C9 H9B 108.0
C11 C10 C9 111.31(10)
C11 C10 H10A 109.4
C9 C10 H10A 109.4
C11 C10 H10B 109.4
C9 C10 H10B 109.4
H10A C10 H10B 108.0
C10 C11 C12 110.79(10)
C10 C11 H11A 109.5
C12 C11 H11A 109.5
C10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.1
C7 C12 C11 111.16(10)
C7 C12 H12A 109.4
C11 C12 H12A 109.4
C7 C12 H12B 109.4
C11 C12 H12B 109.4
H12A C12 H12B 108.0
C18 C13 C14 118.52(10)
C18 C13 C3 123.45(10)
C14 C13 C3 118.01(10)
C15 C14 C13 120.70(11)
C15 C14 H14 119.6
C13 C14 H14 119.6
C14 C15 C16 120.29(11)
C14 C15 H15 119.9
C16 C15 H15 119.9
C17 C16 C15 119.59(10)
C17 C16 H16 120.2
C15 C16 H16 120.2
C16 C17 C18 120.25(11)
C16 C17 H17 119.9
C18 C17 H17 119.9
C13 C18 C17 120.63(11)
C13 C18 H18 119.7
C17 C18 H18 119.7
C20 C19 C24 118.55(10)
C20 C19 C3 122.61(10)
C24 C19 C3 118.83(10)
C19 C20 C21 120.40(11)
C19 C20 H20 119.8
C21 C20 H20 119.8
C22 C21 C20 120.58(11)
C22 C21 H21 119.7
C20 C21 H21 119.7
C21 C22 C23 119.42(11)
C21 C22 H22 120.3
C23 C22 H22 120.3
C22 C23 C24 120.25(12)
C22 C23 H23 119.9
C24 C23 H23 119.9
C23 C24 C19 120.78(11)
C23 C24 H24 119.6
C19 C24 H24 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.3474(14)
O1 C5 1.4802(14)
C2 O2 1.2020(14)
C2 C3 1.5393(15)
C3 C19 1.5315(15)
C3 C4 1.5372(15)
C3 C13 1.5406(15)
C4 C5 1.5222(16)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.4935(16)
C5 H5 1.0000
C6 C7 1.3325(17)
C6 H6 0.9500
C7 C8 1.5056(17)
C7 C12 1.5084(16)
C8 C9 1.5338(18)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C10 1.5244(19)
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.5231(18)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.5307(17)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
C13 C18 1.3908(16)
C13 C14 1.3978(16)
C14 C15 1.3854(16)
C14 H14 0.9500
C15 C16 1.3885(18)
C15 H15 0.9500
C16 C17 1.3810(18)
C16 H16 0.9500
C17 C18 1.3950(17)
C17 H17 0.9500
C18 H18 0.9500
C19 C20 1.3886(16)
C19 C24 1.3969(16)
C20 C21 1.3942(17)
C20 H20 0.9500
C21 C22 1.3808(19)
C21 H21 0.9500
C22 C23 1.3851(19)
C22 H22 0.9500
C23 C24 1.3865(17)
C23 H23 0.9500
C24 H24 0.9500
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
C5 O1 C2 O2 177.86(10)
C5 O1 C2 C3 -0.95(12)
O2 C2 C3 C19 38.84(15)
O1 C2 C3 C19 -142.45(9)
O2 C2 C3 C4 161.57(11)
O1 C2 C3 C4 -19.72(11)
O2 C2 C3 C13 -81.68(14)
O1 C2 C3 C13 97.03(10)
C19 C3 C4 C5 150.41(9)
C2 C3 C4 C5 31.68(10)
C13 C3 C4 C5 -83.83(10)
C2 O1 C5 C6 142.78(9)
C2 O1 C5 C4 21.62(11)
C3 C4 C5 O1 -33.12(10)
C3 C4 C5 C6 -151.01(9)
O1 C5 C6 C7 100.37(14)
C4 C5 C6 C7 -145.37(12)
C5 C6 C7 C8 -1.5(2)
C5 C6 C7 C12 177.68(11)
C6 C7 C8 C9 126.18(13)
C12 C7 C8 C9 -53.01(14)
C7 C8 C9 C10 52.95(14)
C8 C9 C10 C11 -55.12(15)
C9 C10 C11 C12 56.18(14)
C6 C7 C12 C11 -125.03(12)
C8 C7 C12 C11 54.22(14)
C10 C11 C12 C7 -55.15(14)
C19 C3 C13 C18 -112.87(11)
C4 C3 C13 C18 117.89(11)
C2 C3 C13 C18 8.13(14)
C19 C3 C13 C14 65.55(12)
C4 C3 C13 C14 -63.68(12)
C2 C3 C13 C14 -173.45(9)
C18 C13 C14 C15 0.18(16)
C3 C13 C14 C15 -178.32(10)
C13 C14 C15 C16 -0.72(17)
C14 C15 C16 C17 0.47(17)
C15 C16 C17 C18 0.31(17)
C14 C13 C18 C17 0.60(16)
C3 C13 C18 C17 179.02(10)
C16 C17 C18 C13 -0.85(17)
C4 C3 C19 C20 0.97(15)
C2 C3 C19 C20 114.05(11)
C13 C3 C19 C20 -125.54(11)
C4 C3 C19 C24 -178.97(10)
C2 C3 C19 C24 -65.89(12)
C13 C3 C19 C24 54.52(13)
C24 C19 C20 C21 0.75(16)
C3 C19 C20 C21 -179.19(10)
C19 C20 C21 C22 0.34(17)
C20 C21 C22 C23 -0.82(17)
C21 C22 C23 C24 0.20(18)
C22 C23 C24 C19 0.91(18)
C20 C19 C24 C23 -1.37(17)
C3 C19 C24 C23 178.57(10)
