#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:40:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178437 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/58/4025872.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_4025872
loop_
_publ_author_name
'Hui-Jing Li'
'Régis Guillot'
'Vincent Gandon'
_publ_contact_author_address
;Université Paris-sud 11
Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO)
Bâtiment 420
91405 Orsay cedex - France 
;
_publ_contact_author_email       'vincent.gandon@u-psud.fr '
_publ_contact_author_name        'Vincent Gandon'
_publ_contact_author_phone       '01.69.15.39.31 '
_publ_section_title
;
 A Gallium-Catalyzed Cycloisomerization/Friedel-Crafts Tandem
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8435
_journal_page_last               8449
_journal_paper_doi               10.1021/jo101709n
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C25 H30 O6'
_chemical_formula_sum            'C25 H30 O6'
_chemical_formula_weight         426.49
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                109.3720(10)
_cell_angle_beta                 94.3440(10)
_cell_angle_gamma                99.4750(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2634(4)
_cell_length_b                   11.5796(6)
_cell_length_c                   13.9766(7)
_cell_measurement_reflns_used    5781
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      31.83
_cell_measurement_theta_min      2.85
_cell_volume                     1083.07(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16938
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         32.34
_diffrn_reflns_theta_min         1.56
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8APEX II Bruker ICMMO'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         6207
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0382
_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)+(0.0614P)²+0.3382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                5458
_reflns_number_total             6207
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101709n_si_001.cif
_cod_data_source_block           960GuillotICMMO
_cod_database_code               4025872
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 0.88550(12) 0.68498(8) 0.22755(6) 0.01076(15) Uani 1 1 d . . .
C2 C 0.81699(12) 0.57118(8) 0.12885(6) 0.01150(16) Uani 1 1 d . . .
H2A H 0.8959 0.5105 0.1259 0.014 Uiso 1 1 calc R . .
H2B H 0.6892 0.5325 0.1311 0.014 Uiso 1 1 calc R . .
C3 C 0.82069(12) 0.60355(8) 0.03299(6) 0.01094(15) Uani 1 1 d . . .
C4 C 0.92986(12) 0.71381(8) 0.03020(6) 0.01105(15) Uani 1 1 d . . .
C5 C 1.06974(12) 0.76107(8) 0.21410(6) 0.01134(15) Uani 1 1 d . . .
H5A H 1.1625 0.7083 0.2009 0.014 Uiso 1 1 calc R . .
H5B H 1.1173 0.8302 0.2777 0.014 Uiso 1 1 calc R . .
C6 C 1.04833(12) 0.81353(8) 0.12622(6) 0.01076(15) Uani 1 1 d . . .
C7 C 1.24987(12) 0.85052(9) 0.10232(7) 0.01444(17) Uani 1 1 d . . .
H7A H 1.2989 0.7765 0.0723 0.022 Uiso 1 1 calc R . .
H7B H 1.3299 0.9032 0.1646 0.022 Uiso 1 1 calc R . .
H7C H 1.2457 0.8948 0.0553 0.022 Uiso 1 1 calc R . .
C8 C 0.92835(12) 0.73282(8) -0.06377(7) 0.01413(17) Uani 1 1 d . . .
H8 H 0.9996 0.8059 -0.0664 0.017 Uiso 1 1 calc R . .
C9 C 0.82322(13) 0.64541(9) -0.15308(7) 0.01501(17) Uani 1 1 d . . .
H9 H 0.8259 0.6595 -0.2148 0.018 Uiso 1 1 calc R . .
C10 C 0.71360(13) 0.53633(8) -0.14965(7) 0.01423(17) Uani 1 1 d . . .
H10 H 0.6417 0.4775 -0.2088 0.017 Uiso 1 1 calc R . .
C11 C 0.71296(12) 0.51660(8) -0.05747(7) 0.01249(16) Uani 1 1 d . . .
H11 H 0.6394 0.4440 -0.0553 0.015 Uiso 1 1 calc R . .
C12 C 0.96288(12) 0.93173(8) 0.16008(7) 0.01160(16) Uani 1 1 d . . .
C13 C 1.06178(12) 1.03617(8) 0.24346(7) 0.01324(16) Uani 1 1 d . . .
H13 H 1.1760 1.0317 0.2755 0.016 Uiso 1 1 calc R . .
C14 C 0.99323(13) 1.14487(8) 0.27874(7) 0.01353(16) Uani 1 1 d . . .
C15 C 0.82183(13) 1.15434(8) 0.23006(7) 0.01404(17) Uani 1 1 d . . .
C16 C 0.72380(12) 1.05250(8) 0.14797(7) 0.01416(17) Uani 1 1 d . . .
H16 H 0.6107 1.0575 0.1151 0.017 Uiso 1 1 calc R . .
C17 C 0.79343(12) 0.94177(8) 0.11387(7) 0.01319(16) Uani 1 1 d . . .
H17 H 0.7246 0.8739 0.0593 0.016 Uiso 1 1 calc R . .
C18 C 1.25172(14) 1.24283(9) 0.41283(8) 0.01986(19) Uani 1 1 d . . .
H18A H 1.2308 1.1741 0.4373 0.030 Uiso 1 1 calc R . .
H18B H 1.2961 1.3194 0.4698 0.030 Uiso 1 1 calc R . .
H18C H 1.3443 1.2310 0.3668 0.030 Uiso 1 1 calc R . .
C19 C 0.60951(15) 1.28456(10) 0.21348(9) 0.0221(2) Uani 1 1 d . . .
H19A H 0.6347 1.2746 0.1451 0.033 Uiso 1 1 calc R . .
H19B H 0.5879 1.3673 0.2464 0.033 Uiso 1 1 calc R . .
H19C H 0.4998 1.2242 0.2111 0.033 Uiso 1 1 calc R . .
C20 C 0.73267(12) 0.76250(8) 0.25375(7) 0.01219(16) Uani 1 1 d . . .
C21 C 0.66160(14) 0.94238(9) 0.37276(8) 0.01978(19) Uani 1 1 d . . .
H21A H 0.5487 0.8975 0.3875 0.024 Uiso 1 1 calc R . .
H21B H 0.6260 0.9729 0.3187 0.024 Uiso 1 1 calc R . .
C22 C 0.75796(17) 1.05011(10) 0.46758(8) 0.0253(2) Uani 1 1 d . . .
H22A H 0.7950 1.0187 0.5200 0.038 Uiso 1 1 calc R . .
H22B H 0.6726 1.1051 0.4914 0.038 Uiso 1 1 calc R . .
H22C H 0.8675 1.0951 0.4516 0.038 Uiso 1 1 calc R . .
C23 C 0.90522(12) 0.63272(8) 0.31412(7) 0.01221(16) Uani 1 1 d . . .
C24 C 1.10348(14) 0.57461(9) 0.42316(7) 0.01702(18) Uani 1 1 d . . .
H24A H 1.0412 0.4872 0.3954 0.020 Uiso 1 1 calc R . .
H24B H 1.0474 0.6161 0.4828 0.020 Uiso 1 1 calc R . .
C25 C 1.31106(15) 0.58646(11) 0.45221(9) 0.0246(2) Uani 1 1 d . . .
H25A H 1.3627 0.5388 0.3941 0.037 Uiso 1 1 calc R . .
H25B H 1.3303 0.5555 0.5072 0.037 Uiso 1 1 calc R . .
H25C H 1.3727 0.6727 0.4739 0.037 Uiso 1 1 calc R . .
O1 O 1.07978(10) 1.24882(6) 0.36035(5) 0.01710(14) Uani 1 1 d . . .
O2 O 0.76724(10) 1.26614(6) 0.26984(6) 0.01927(15) Uani 1 1 d . . .
O3 O 0.79384(9) 0.86067(6) 0.34128(5) 0.01506(14) Uani 1 1 d . . .
O4 O 0.57858(9) 0.73899(6) 0.20571(5) 0.01731(14) Uani 1 1 d . . .
O5 O 0.76926(9) 0.59105(7) 0.34635(5) 0.01723(14) Uani 1 1 d . . .
O6 O 1.08249(9) 0.63328(6) 0.34622(5) 0.01475(14) Uani 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
C23 C1 C20 104.34(7) . . ?
C23 C1 C2 106.03(7) . . ?
C20 C1 C2 110.77(7) . . ?
C23 C1 C5 114.34(7) . . ?
C20 C1 C5 112.59(7) . . ?
C2 C1 C5 108.55(7) . . ?
C3 C2 C1 113.29(7) . . ?
C4 C3 C11 119.36(8) . . ?
C4 C3 C2 122.99(8) . . ?
C11 C3 C2 117.63(7) . . ?
C8 C4 C3 118.42(8) . . ?
C8 C4 C6 119.46(8) . . ?
C3 C4 C6 122.12(7) . . ?
C1 C5 C6 113.94(7) . . ?
C4 C6 C12 111.03(7) . . ?
C4 C6 C5 110.78(7) . . ?
C12 C6 C5 110.95(7) . . ?
C4 C6 C7 109.12(7) . . ?
C12 C6 C7 108.31(7) . . ?
C5 C6 C7 106.50(7) . . ?
C9 C8 C4 121.75(8) . . ?
C8 C9 C10 119.56(8) . . ?
C11 C10 C9 119.34(8) . . ?
C10 C11 C3 121.57(8) . . ?
C17 C12 C13 117.64(8) . . ?
C17 C12 C6 124.00(8) . . ?
C13 C12 C6 118.35(7) . . ?
C14 C13 C12 121.66(8) . . ?
O1 C14 C13 124.79(8) . . ?
O1 C14 C15 115.14(8) . . ?
C13 C14 C15 120.07(8) . . ?
O2 C15 C16 125.62(8) . . ?
O2 C15 C14 115.62(8) . . ?
C16 C15 C14 118.76(8) . . ?
C15 C16 C17 120.63(8) . . ?
C12 C17 C16 121.23(8) . . ?
O4 C20 O3 124.17(8) . . ?
O4 C20 C1 125.80(8) . . ?
O3 C20 C1 110.00(7) . . ?
O3 C21 C22 107.42(8) . . ?
O5 C23 O6 124.38(8) . . ?
O5 C23 C1 121.90(8) . . ?
O6 C23 C1 113.67(7) . . ?
O6 C24 C25 107.31(8) . . ?
C14 O1 C18 117.11(7) . . ?
C15 O2 C19 116.65(8) . . ?
C20 O3 C21 114.91(7) . . ?
C23 O6 C24 114.55(7) . . ?
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 C23 1.5293(12) . ?
C1 C20 1.5309(12) . ?
C1 C2 1.5367(11) . ?
C1 C5 1.5370(12) . ?
C2 C3 1.5071(12) . ?
C3 C4 1.4018(12) . ?
C3 C11 1.4038(12) . ?
C4 C8 1.4014(12) . ?
C4 C6 1.5313(11) . ?
C5 C6 1.5488(12) . ?
C6 C12 1.5418(12) . ?
C6 C7 1.5494(12) . ?
C8 C9 1.3888(12) . ?
C9 C10 1.3951(13) . ?
C10 C11 1.3814(13) . ?
C12 C17 1.3863(12) . ?
C12 C13 1.4103(12) . ?
C13 C14 1.3811(12) . ?
C14 O1 1.3699(11) . ?
C14 C15 1.4110(13) . ?
C15 O2 1.3665(11) . ?
C15 C16 1.3843(12) . ?
C16 C17 1.4042(12) . ?
C18 O1 1.4234(12) . ?
C19 O2 1.4261(12) . ?
C20 O4 1.2009(11) . ?
C20 O3 1.3472(11) . ?
C21 O3 1.4485(11) . ?
C21 C22 1.5092(15) . ?
C23 O5 1.2106(11) . ?
C23 O6 1.3293(11) . ?
C24 O6 1.4612(11) . ?
C24 C25 1.5030(14) . ?
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
C23 C1 C2 C3 -170.33(7) . . . . ?
C20 C1 C2 C3 77.05(9) . . . . ?
C5 C1 C2 C3 -47.05(9) . . . . ?
C1 C2 C3 C4 19.74(11) . . . . ?
C1 C2 C3 C11 -162.02(7) . . . . ?
C11 C3 C4 C8 -0.45(12) . . . . ?
C2 C3 C4 C8 177.75(8) . . . . ?
C11 C3 C4 C6 179.07(8) . . . . ?
C2 C3 C4 C6 -2.73(13) . . . . ?
C23 C1 C5 C6 179.97(7) . . . . ?
C20 C1 C5 C6 -61.17(9) . . . . ?
C2 C1 C5 C6 61.84(9) . . . . ?
C8 C4 C6 C12 70.26(10) . . . . ?
C3 C4 C6 C12 -109.25(9) . . . . ?
C8 C4 C6 C5 -165.99(8) . . . . ?
C3 C4 C6 C5 14.50(11) . . . . ?
C8 C4 C6 C7 -49.04(10) . . . . ?
C3 C4 C6 C7 131.44(8) . . . . ?
C1 C5 C6 C4 -44.59(9) . . . . ?
C1 C5 C6 C12 79.21(9) . . . . ?
C1 C5 C6 C7 -163.13(7) . . . . ?
C3 C4 C8 C9 -0.41(13) . . . . ?
C6 C4 C8 C9 -179.94(8) . . . . ?
C4 C8 C9 C10 0.96(14) . . . . ?
C8 C9 C10 C11 -0.62(13) . . . . ?
C9 C10 C11 C3 -0.25(13) . . . . ?
C4 C3 C11 C10 0.79(13) . . . . ?
C2 C3 C11 C10 -177.51(8) . . . . ?
C4 C6 C12 C17 4.60(11) . . . . ?
C5 C6 C12 C17 -119.05(9) . . . . ?
C7 C6 C12 C17 124.39(9) . . . . ?
C4 C6 C12 C13 -175.77(7) . . . . ?
C5 C6 C12 C13 60.58(10) . . . . ?
C7 C6 C12 C13 -55.98(10) . . . . ?
C17 C12 C13 C14 0.26(13) . . . . ?
C6 C12 C13 C14 -179.39(8) . . . . ?
C12 C13 C14 O1 178.70(8) . . . . ?
C12 C13 C14 C15 -1.13(14) . . . . ?
O1 C14 C15 O2 0.95(12) . . . . ?
C13 C14 C15 O2 -179.20(8) . . . . ?
O1 C14 C15 C16 -178.91(8) . . . . ?
C13 C14 C15 C16 0.94(13) . . . . ?
O2 C15 C16 C17 -179.74(9) . . . . ?
C14 C15 C16 C17 0.10(13) . . . . ?
C13 C12 C17 C16 0.80(13) . . . . ?
C6 C12 C17 C16 -179.57(8) . . . . ?
C15 C16 C17 C12 -0.99(14) . . . . ?
C23 C1 C20 O4 -112.94(10) . . . . ?
C2 C1 C20 O4 0.75(12) . . . . ?
C5 C1 C20 O4 122.51(9) . . . . ?
C23 C1 C20 O3 65.32(8) . . . . ?
C2 C1 C20 O3 179.01(7) . . . . ?
C5 C1 C20 O3 -59.23(9) . . . . ?
C20 C1 C23 O5 42.82(10) . . . . ?
C2 C1 C23 O5 -74.20(10) . . . . ?
C5 C1 C23 O5 166.24(8) . . . . ?
C20 C1 C23 O6 -139.75(7) . . . . ?
C2 C1 C23 O6 103.23(8) . . . . ?
C5 C1 C23 O6 -16.32(10) . . . . ?
C13 C14 O1 C18 -0.79(13) . . . . ?
C15 C14 O1 C18 179.05(8) . . . . ?
C16 C15 O2 C19 -8.80(14) . . . . ?
C14 C15 O2 C19 171.35(8) . . . . ?
O4 C20 O3 C21 -2.80(13) . . . . ?
C1 C20 O3 C21 178.90(7) . . . . ?
C22 C21 O3 C20 -176.57(8) . . . . ?
O5 C23 O6 C24 2.02(12) . . . . ?
C1 C23 O6 C24 -175.34(7) . . . . ?
C25 C24 O6 C23 -178.63(8) . . . . ?
