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_1550131
_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 ad
_chemical_formula_moiety         'C16 H20 O2'
_chemical_formula_sum            'C16 H20 O2'
_chemical_formula_weight         244.32
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-03
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2018-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.52630(10)
_cell_length_b                   7.5880(2)
_cell_length_c                   31.5641(6)
_cell_measurement_reflns_used    7361
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      78.7320
_cell_measurement_theta_min      5.5690
_cell_volume                     1323.60(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45f (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -73.00  23.00   0.50    0.50    --    0.00 -82.00-144.00  192
  2  \w    -75.00   8.00   0.50    0.50    --    0.00 -43.00  -6.00  166
  3  \w      9.00  34.00   0.50    0.50    --    0.00  43.00 145.00   50
  4  \w    -92.00 -67.00   0.50    0.50    -- -100.00 110.00-133.00   50
  5  \w   -149.00-123.00   0.50    0.50    -- -100.00 -82.00-144.00   52
  6  \w    -76.00 -51.00   0.50    0.50    -- -100.00  43.00 145.00   50
  7  \w   -158.00-133.00   0.50    0.50    -- -100.00 -43.00  -6.00   50
  8  \w   -135.00-109.00   0.50    0.50    -- -100.00-110.00 132.00   52
  9  \w    105.00 130.00   0.50    0.50    --  106.00 110.00-133.00   50
 10  \w    106.00 131.00   0.50    0.50    --  106.00  82.00 -22.00   50
 11  \w     57.00  82.00   0.50    0.50    --  106.00 -82.00-144.00   50
 12  \w    152.00 178.00   0.50    0.50    --  106.00  43.00 145.00   52
 13  \w     16.00  42.00   0.50    0.50    --    0.00  77.00  60.00   52
 14  \w      2.00  31.00   0.50    0.50    --    0.00 -99.00   0.00   58
 15  \w    -57.00   7.00   0.50    0.50    --    0.00 -38.00 150.00  128
 16  \w    -72.00 -26.00   0.50    0.50    -- -100.00  30.00  60.00   92
 17  \w    -80.00 -26.00   0.50    0.50    -- -100.00  45.00-120.00  108
 18  \w    -71.00 -28.00   0.50    0.50    -- -100.00  30.00 -30.00   86
 19  \w    -70.00 -23.00   0.50    0.50    -- -100.00  30.00-150.00   94
 20  \w    -77.00 -26.00   0.50    0.50    -- -100.00  45.00 -90.00  102
 21  \w     30.00  57.00   0.50    0.50    --  106.00 -94.00  60.00   54
 22  \w     31.00  69.00   0.50    0.50    --  106.00 -45.00  30.00   76
 23  \w     31.00  61.00   0.50    0.50    --  106.00 -30.00  30.00   60
 24  \w     71.00 109.00   0.50    0.50    --  106.00 -94.00  60.00   76
 25  \w     70.00 108.00   0.50    0.50    --  106.00 -94.00-150.00   76
 26  \w     31.00  65.00   0.50    0.50    --  106.00 -94.00-150.00   68
 27  \w     36.00  72.00   0.50    0.50    --  106.00 -45.00 -90.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, Pilatus 200K'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0278463000
_diffrn_orient_matrix_UB_12      0.0380591000
_diffrn_orient_matrix_UB_13      -0.0476948000
_diffrn_orient_matrix_UB_21      0.2418839000
_diffrn_orient_matrix_UB_22      0.1010171000
_diffrn_orient_matrix_UB_23      0.0003204000
_diffrn_orient_matrix_UB_31      0.1356902000
_diffrn_orient_matrix_UB_32      -0.1719560000
_diffrn_orient_matrix_UB_33      -0.0103772000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            8543
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.490
_diffrn_reflns_theta_min         5.607
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.45f (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.32(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2588
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0330
_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^)+(0.0482P)^2^+0.3399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                2552
_reflns_number_total             2588
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03835j2.cif
_cod_data_source_block           rr001
_cod_database_code               1550131
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C O H'
_reflns_odcompleteness_completeness 99.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C14(H14), C2(H2)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C5(H5A,H5B,H5C)
;
_shelx_res_checksum              13908
_shelx_hkl_checksum              45549
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.612
_oxdiff_exptl_absorpt_empirical_full_min 0.634