A Copper-Catalyzed Double Coupling Enables a 3-Step Synthesis of the Quassinoid Core Architecture
Condakes, Matthew; Rosen, Rachel; Harwood, Stephen; Maimone, Thomas; Chemical Science  (2019) –; doi:10.1039/C8SC03835J

data_1550136
_publ_section_title
;
 A Copper-Catalyzed Double Coupling Enables a 3-Step Synthesis of the
 Quassinoid Core Architecture
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C8SC03835J
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C18 H24 O5'
_chemical_formula_sum            'C18 H24 O5'
_chemical_formula_weight         320.39
_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_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2018-07-09
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7797(15)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0320(3)
_cell_length_b                   6.3518(2)
_cell_length_c                   16.1371(6)
_cell_measurement_reflns_used    16547
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.5250
_cell_measurement_theta_min      5.8380
_cell_volume                     821.49(5)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      99.97
_diffrn_measured_fraction_theta_full 0.9884
_diffrn_measured_fraction_theta_max 0.9884
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20223
_diffrn_reflns_theta_full        68.2754
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.768
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2951
_exptl_crystal_description       block
_exptl_crystal_F_000             345.1788
_refine_diff_density_max         0.1328
_refine_diff_density_min         -0.1242
_refine_diff_density_rms         0.0283
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(11)
_refine_ls_d_res_high            0.8298
_refine_ls_d_res_low             16.1020
_refine_ls_goodness_of_fit_ref   1.0956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    4
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0956
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0243
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0310P)^2^+0.1140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0620
_reflns_Friedel_coverage         0.977
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              7
_reflns_limit_k_min              -7
_reflns_limit_l_max              19
_reflns_limit_l_min              -19
_reflns_number_gt                2920
_reflns_number_total             2984
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c8sc03835j2.cif
_cod_data_source_block           MLC_LIT_dioxenecoupling
_cod_database_code               1550136
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_date_sample_completion    2015-05-27
_olex2_date_sample_data_collection 2015-05-26
_olex2_date_sample_submission    2015-05-26
_olex2_submission_original_sample_id MLC-II-225
_olex2_submission_special_instructions 'No special instructions were received'