Regioselective Synthesis of Bicyclic and Polycyclic Systems by Cycloaddition Reactions of Alkenyl p-Benzoquinones
Bisht, Shweta; Rani, Rashmi; Peddinti, Rama Krishna; The Journal of Organic Chemistry  (2017) –; doi:10.1021/acs.joc.7b02377

data_4033261
_publ_section_title
;
 Regioselective Synthesis of Bicyclic and Polycyclic Systems by
 Cycloaddition Reactions of Alkenyl p-Benzoquinones
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02377
_journal_year                    2017
_chemical_formula_moiety         'C17 H16 O7'
_chemical_formula_sum            'C17 H16 O7'
_chemical_formula_weight         332.30
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.071(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7348(17)
_cell_length_b                   11.031(2)
_cell_length_c                   18.970(4)
_cell_measurement_reflns_used    4024
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.418
_cell_measurement_theta_min      0.970
_cell_volume                     1598.3(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 'phi and omega scans'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector''
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0838
_diffrn_reflns_av_unetI/netI     0.0857
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20107
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.418
_diffrn_reflns_theta_min         2.667
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       0.072(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.316
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.316
_refine_ls_R_factor_all          0.2126
_refine_ls_R_factor_gt           0.1334
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3750
_refine_ls_wR_factor_ref         0.4194
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1842
_reflns_number_total             3933
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02377_si_003.cif
_cod_data_source_block           ups3130_rkb_ssb_1_0ma
_cod_database_code               4033261
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.970
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C6(H6), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C2(H2), C3(H3), C9(H9)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C15(H15A,H15B,H15C), C11(H11A,H11B,H11C)
;
_shelx_res_checksum              88027
_shelx_hkl_checksum              22782
_olex2_submission_special_instructions 'No special instructions were received'