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_1550132
_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_formula_moiety         'C11 H16 O'
_chemical_formula_sum            'C11 H16 O'
_chemical_formula_weight         164.24
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-30
_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            16
_cell_length_a                   22.7253(4)
_cell_length_b                   22.7253(4)
_cell_length_c                   7.5782(2)
_cell_measurement_reflns_used    5853
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.6360
_cell_measurement_theta_min      3.8740
_cell_volume                     3913.68(14)
_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 0.998
_diffrn_measured_fraction_theta_max 0.972
_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    -15.00  31.00   0.50    1.41    --    0.00 -99.00-120.00   92
  2  \w    -77.00   7.00   0.50    1.41    --    0.00 -38.00 -30.00  168
  3  \w    -79.00   6.00   0.50    1.41    --    0.00 -17.00 175.00  170
  4  \w    138.00 174.00   0.50    5.64    --  106.00  15.00   0.00   72
  5  \w    104.00 135.00   0.50    5.64    --  106.00  15.00   0.00   62
  6  \w     40.00  66.00   0.50    5.64    --  106.00 -30.00-150.00   52
  7  \w     33.00  68.00   0.50    5.64    --  106.00 -45.00   0.00   70
  8  \w     31.00  66.00   0.50    5.64    --  106.00 -30.00  30.00   70
  9  \w     31.00  74.00   0.50    5.64    --  106.00 -45.00  30.00   86
 10  \w     31.00  60.00   0.50    5.64    --  106.00 -30.00 120.00   58
 11  \w     33.00  72.00   0.50    5.64    --  106.00 -45.00 120.00   78
 12  \w     35.00 135.00   0.50    5.64    --  106.00-150.00 172.00  200
 13  \w    -78.00 -48.00   0.50    5.64    -- -100.00  45.00  60.00   60
 14  \w   -112.00 -24.00   0.50    5.64    -- -100.00 111.00 153.00  176
 15  \w   -108.00 -33.00   0.50    5.64    -- -100.00 111.00 150.00  150
 16  \w   -175.00 -80.00   0.50    5.64    -- -100.00-123.00 -25.00  190
;
_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      -0.0025809000
_diffrn_orient_matrix_UB_12      0.0650540000
_diffrn_orient_matrix_UB_13      0.0561698000
_diffrn_orient_matrix_UB_21      -0.0149869000
_diffrn_orient_matrix_UB_22      0.0177579000
_diffrn_orient_matrix_UB_23      -0.1909423000
_diffrn_orient_matrix_UB_31      -0.0660984000
_diffrn_orient_matrix_UB_32      -0.0066393000
_diffrn_orient_matrix_UB_33      0.0413164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10823
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.073
_diffrn_reflns_theta_min         3.890
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.533
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72366
_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    1.115
_exptl_crystal_description       needle
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0529
_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^)+(0.0628P)^2^+4.5410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1431
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1828
_reflns_number_total             2055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc03835j2.cif
_cod_data_source_block           mc003
_cod_original_cell_volume        3913.68(17)
_cod_database_code               1550132
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C11 H16 O1'
_shelx_estimated_absorpt_t_max   0.974
_shelx_estimated_absorpt_t_min   0.883
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_olex2_refinement_description
;
;
_shelx_res_checksum              41973
_shelx_hkl_checksum              37118
_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 1.447
_oxdiff_exptl_absorpt_empirical_full_min 0.691