Constructing Densely Functionalized Hajos–Parrish-type Ketones with Six Contiguous Stereogenic Centers and Two Quaternary Carbons in a Formal [2 + 2 + 2] Cycloaddition Cascade
Peng, Chieh-Hung; Hong, Bor-Cherng; Raja, Arun; Chang, Chun-Wei; Lee, Gene-Hsiang; RSC Adv.  (2016) –; doi:10.1039/C6RA22430J

data_7226657
_publ_section_title
;
 Constructing Densely Functionalized Hajos--Parrish-type Ketones with Six
 Contiguous Stereogenic Centers and Two Quaternary Carbons in a Formal [2
 + 2 + 2] Cycloaddition Cascade
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA22430J
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_sum            'C22 H22 N2 O6'
_chemical_formula_weight         410.41
_chemical_name_common            ic18058-1
_chemical_name_systematic        5a
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-09-23 deposited with the CCDC.
2016-09-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.60530(10)
_cell_length_b                   16.3208(3)
_cell_length_c                   18.4301(3)
_cell_measurement_reflns_used    9909
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      70.19
_cell_measurement_theta_min      3.62
_cell_volume                     1986.83(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9468
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.976
_diffrn_reflns_theta_min         3.617
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.506
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
; 
 Flack x determined using 1508 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.52(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3755
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0461P)^2^+0.3152P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0800
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3652
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_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra22430j2.cif
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_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.676
_shelx_estimated_absorpt_t_max   0.948
_shelx_res_checksum              37117