Addition, Substitution, and Ring-Contraction Reactions of Quinones with N-Heterocyclic Carbenes.
Ping, Lucy; Bak, JungMin; Kim, Youngmee; Bouffard, Jean; The Journal of organic chemistry 83 (2018) 9240–9249; doi:10.1021/acs.joc.8b01236

data_4035326
_publ_section_title
;
 Addition, Substitution, and Ring-Contraction Reactions of Quinones with
 N-Heterocyclic Carbenes.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9240
_journal_page_last               9249
_journal_paper_doi               10.1021/acs.joc.8b01236
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C29 H24 Cl2 N4 O2'
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_atom_sites_solution_hydrogens   geom
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_cell_angle_beta                 94.4057(7)
_cell_angle_gamma                90
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_cell_length_b                   17.6729(2)
_cell_length_c                   16.5085(2)
_cell_measurement_reflns_used    9272
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.2453
_cell_measurement_theta_min      2.3048
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_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
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_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
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_diffrn_reflns_theta_max         28.619
_diffrn_reflns_theta_min         1.691
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'dark purple'
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       block
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
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_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         6739
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0541P)^2^+0.7102P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1251
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4645
_reflns_number_total             6739
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01236_si_005.cif
_cod_data_source_block           9b
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4035326
_shelx_estimated_absorpt_t_min   0.957
_shelx_estimated_absorpt_t_max   0.967
_shelxl_version_number           2013-4
_shelx_res_checksum              8751
_shelx_hkl_checksum              95838