#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:56:23 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180281 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/67/7116782.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_7116782
loop_
_publ_author_name
'M. Presset'
'B. Michelet'
'R. Guillot'
'C. Bour'
'S. Bezzenine-Lafollee'
'V. Gandon'
_publ_section_title
;
 Gallium(III)- and calcium(II)-catalyzed Meyer-Schuster rearrangements
 followed by intramolecular aldol condensation or endo-Michael addition
;
_journal_name_full               Chem.Commun.
_journal_page_first              5318
_journal_paper_doi               10.1039/C4cc09514F
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C17 H20 O4'
_chemical_formula_sum            'C17 H20 O4'
_chemical_formula_weight         288.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc12lvzh
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-05-05 deposited with the CCDC.
2014-12-07 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.7310(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3539(3)
_cell_length_b                   11.1450(3)
_cell_length_c                   16.1987(5)
_cell_measurement_temperature    100(1)
_cell_volume                     1476.67(8)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26630
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         2.23
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'kappa X8 APEX II Bruke rICMMO'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9954
_exptl_absorpt_correction_T_min  0.9784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0415
_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)+(0.0479P)²+0.4124P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1080
_reflns_number_gt                3431
_reflns_number_total             4434
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc09514f2.cif
_cod_data_source_block           1968GuillotICMMO
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7116782
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.65652(13) 0.33613(9) -0.11819(7) 0.0135(2) Uani 1 1 d .
C2 C 1.02357(13) 0.42273(9) -0.14544(7) 0.0129(2) Uani 1 1 d .
H2 H 1.1142 0.4565 -0.1039 0.016 Uiso 1 1 calc R
C3 C 1.09171(13) 0.40218(9) -0.22478(7) 0.0135(2) Uani 1 1 d .
C4 C 1.11157(13) 0.25853(10) -0.03769(7) 0.0140(2) Uani 1 1 d .
C5 C 0.89043(14) 0.52154(9) -0.16089(7) 0.0149(2) Uani 1 1 d .
H5A H 0.8653 0.5434 -0.1070 0.018 Uiso 1 1 calc R
H5B H 0.9359 0.5920 -0.1828 0.018 Uiso 1 1 calc R
C6 C 1.06408(15) 0.30014(10) -0.27513(8) 0.0188(2) Uani 1 1 d .
H6 H 1.0007 0.2381 -0.2607 0.023 Uiso 1 1 calc R
C7 C 0.97249(13) 0.30703(9) -0.10433(7) 0.0125(2) Uani 1 1 d .
H7 H 0.9407 0.2460 -0.1481 0.015 Uiso 1 1 calc R
C8 C 0.73300(14) 0.48975(10) -0.22025(7) 0.0153(2) Uani 1 1 d .
C9 C 0.66022(14) 0.36812(10) -0.21025(7) 0.0148(2) Uani 1 1 d .
H9A H 0.7230 0.3077 -0.2328 0.018 Uiso 1 1 calc R
H9B H 0.5495 0.3660 -0.2432 0.018 Uiso 1 1 calc R
C10 C 0.82747(13) 0.33125(9) -0.06197(7) 0.0131(2) Uani 1 1 d .
C11 C 1.18644(14) 0.49383(10) -0.24906(8) 0.0172(2) Uani 1 1 d .
H11 H 1.2053 0.5632 -0.2166 0.021 Uiso 1 1 calc R
C12 C 0.58324(14) 0.20962(10) -0.11625(8) 0.0189(2) Uani 1 1 d .
H12A H 0.5790 0.1888 -0.0592 0.028 Uiso 1 1 calc R
H12B H 0.6503 0.1527 -0.1381 0.028 Uiso 1 1 calc R
H12C H 0.4748 0.2085 -0.1502 0.028 Uiso 1 1 calc R
C13 C 1.25282(14) 0.48366(11) -0.32044(8) 0.0212(3) Uani 1 1 d .
H13 H 1.3157 0.5458 -0.3353 0.025 Uiso 1 1 calc R
C14 C 1.22578(15) 0.38121(12) -0.36966(8) 0.0222(3) Uani 1 1 d .
H14 H 1.2711 0.3738 -0.4173 0.027 Uiso 1 1 calc R
C15 C 0.55143(14) 0.42576(10) -0.08169(8) 0.0189(2) Uani 1 1 d .
H15A H 0.5488 0.4038 -0.0247 0.028 Uiso 1 1 calc R
H15B H 0.4423 0.4252 -0.1150 0.028 Uiso 1 1 calc R
H15C H 0.5971 0.5047 -0.0825 0.028 Uiso 1 1 calc R
C16 C 1.13068(16) 0.29008(11) -0.34719(8) 0.0230(3) Uani 1 1 d .
H16 H 1.1109 0.2215 -0.3804 0.028 Uiso 1 1 calc R
C17 C 1.19919(17) 0.09189(12) 0.04874(9) 0.0267(3) Uani 1 1 d .
H17A H 1.3030 0.0845 0.0324 0.040 Uiso 1 1 calc R
H17B H 1.1619 0.0140 0.0617 0.040 Uiso 1 1 calc R
H17C H 1.2106 0.1424 0.0976 0.040 Uiso 1 1 calc R
O1 O 0.84789(10) 0.34282(8) 0.01378(5) 0.01896(18) Uani 1 1 d .
O2 O 0.66513(11) 0.56091(8) -0.27285(6) 0.02172(19) Uani 1 1 d .
O3 O 1.23036(10) 0.31354(7) -0.00354(6) 0.02141(19) Uani 1 1 d .
O4 O 1.08182(10) 0.14431(7) -0.01973(5) 0.01869(18) 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
C15 C1 C10 109.47(9)
C15 C1 C12 109.21(9)
C10 C1 C12 106.38(9)
C15 C1 C9 110.49(9)
C10 C1 C9 112.61(9)
C12 C1 C9 108.55(9)
C3 C2 C5 110.45(9)
C3 C2 C7 114.81(9)
C5 C2 C7 114.16(8)
C6 C3 C11 117.95(10)
C6 C3 C2 124.82(10)
C11 C3 C2 117.22(10)
O3 C4 O4 123.85(10)
O3 C4 C7 125.99(10)
O4 C4 C7 110.13(9)
C8 C5 C2 116.19(9)
C3 C6 C16 120.60(11)
C4 C7 C10 107.76(9)
C4 C7 C2 111.37(9)
C10 C7 C2 110.95(8)
O2 C8 C5 121.08(10)
O2 C8 C9 121.37(11)
C5 C8 C9 117.52(9)
C8 C9 C1 113.58(9)
O1 C10 C1 121.42(10)
O1 C10 C7 120.74(10)
C1 C10 C7 117.81(9)
C13 C11 C3 121.41(11)
C14 C13 C11 120.14(11)
C16 C14 C13 119.30(11)
C14 C16 C6 120.59(12)
C4 O4 C17 115.06(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C15 1.5261(15)
C1 C10 1.5307(15)
C1 C12 1.5400(15)
C1 C9 1.5398(15)
C2 C3 1.5249(15)
C2 C5 1.5489(15)
C2 C7 1.5505(15)
C3 C6 1.3912(16)
C3 C11 1.3968(15)
C4 O3 1.2014(14)
C4 O4 1.3403(13)
C4 C7 1.5158(15)
C5 C8 1.5051(16)
C6 C16 1.3960(17)
C7 C10 1.5328(15)
C8 O2 1.2165(14)
C8 C9 1.5078(15)
C10 O1 1.2108(14)
C11 C13 1.3849(17)
C13 C14 1.3846(19)
C14 C16 1.3830(18)
C17 O4 1.4458(14)
