Convergent Access to Polycyclic Cyclopentanoids from α,β-Unsaturated Acid Chlorides and Alkynes through a Reductive Coupling, Nazarov Cyclization Sequence.
Chaplin, Jason H; Jackson, Kristal; White, Jonathan M; Flynn, Bernard L; The Journal of organic chemistry 79 (2014) 3659–3664; doi:10.1021/jo500040b

data_4029277
_publ_section_title
;
 Convergent Access to Polycyclic Cyclopentanoids from \a,\b-Unsaturated
 Acid Chlorides and Alkynes through a Reductive Coupling, Nazarov
 Cyclization Sequence.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3659
_journal_page_last               3664
_journal_paper_doi               10.1021/jo500040b
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration syn
_chemical_formula_sum            'C30 H27 N O6'
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_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
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_cell_angle_alpha                90
_cell_angle_beta                 99.471(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1224(11)
_cell_length_b                   12.237(2)
_cell_length_c                   16.495(3)
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_cell_measurement_temperature    130.0(1)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      3.01
_cell_volume                     1219.0(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_diffrn_ambient_temperature      130.0(1)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6410
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.082
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         4026
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0385
_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/[\s^2^(Fo^2^)+(0.0547P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                3757
_reflns_number_total             4026
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo500040b_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;Adding full bibliography for
 ./tmp-cod-update-bibliographies-12971/cifs/4029277.cif.
;
_cod_database_code               4029277
_shelxl_version_number           2012-9