A two-step, stereoselective synthesis of nine- and ten-membered carbocycles from phthalates.
Prado, Gustavo; Veiga, Alberte X.; Fernández-Nieto, Fernando; Paleo, M. Rita; Sardina, F. Javier; Organic letters 17 (2015) 2054–2057; doi:10.1021/acs.orglett.5b00552

data_1554880
_publ_section_title
;
 A two-step, stereoselective synthesis of nine- and ten-membered
 carbocycles from phthalates.
;
_journal_issue                   9
_journal_name_full               'Organic letters'
_journal_page_first              2054
_journal_page_last               2057
_journal_paper_doi               10.1021/acs.orglett.5b00552
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C13 H22 O2'
_chemical_formula_sum            'C13 H22 O2'
_chemical_formula_weight         210.31
_chemical_name_common            JSGP1059
_chemical_name_systematic
;
 trans-(6Z,8Z)-1,5-Dimethylcyclonona-6,8-diene-1,5-diyl)dimethanol
;
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      9
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-25T12:51:55-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 114.771(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0887(5)
_cell_length_b                   10.5929(4)
_cell_length_c                   9.0247(3)
_cell_measurement_reflns_used    468
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.5
_cell_measurement_wavelength     0.71073
_cell_volume                     1222.92(8)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SIR-2011 (Burla et al., 2012)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      4
_diffrn_orient_matrix_UB_12      0.052191
_diffrn_orient_matrix_UB_13      0.068712
_diffrn_orient_matrix_UB_21      4
_diffrn_orient_matrix_UB_22      0.054611
_diffrn_orient_matrix_UB_23      -0.06468
_diffrn_orient_matrix_UB_31      4
_diffrn_orient_matrix_UB_32      -0.020112
_diffrn_orient_matrix_UB_33      0.002682
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.083
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16365
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.624
_diffrn_reflns_theta_min         2.496
_diffrn_source                   'sealed x-ray tube'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
TWINABS - Bruker AXS scaling for twinned crystals - Version 2012/1
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.142
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 1231 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     147
_refine_ls_number_reflns         16365
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0413P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.099
_reflns_number_gt                13409
_reflns_number_total             16365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b00552_si_003.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               1554880
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.99