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_4035327
_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            'C32 H36 Cl4 N2'
_chemical_formula_weight         590.43
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           'APEX2 v2014.1-1'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   16.5113(4)
_cell_length_b                   18.4826(4)
_cell_length_c                   31.1034(7)
_cell_measurement_reflns_used    9200
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.84
_cell_measurement_theta_min      2.30
_cell_volume                     9491.9(4)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_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 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0772
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            279370
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.282
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       block
_exptl_crystal_F_000             3720
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
; 
 Flack x determined using 4955 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.017(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1051
_refine_ls_number_reflns         17636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0437
_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^)+(0.0322P)^2^+3.9991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0983
_reflns_Friedel_coverage         0.838
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                12819
_reflns_number_total             17636
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01236_si_003.cif
_cod_data_source_block           7a
_cod_depositor_comments
;

2020-07-21
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C96 H108 Cl12 N6'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1771.28
_cod_database_code               4035327
_shelx_estimated_absorpt_t_min   0.932
_shelx_estimated_absorpt_t_max   0.943
_shelxl_version_number           2013-4
_shelx_res_checksum              89292
_shelx_hkl_checksum              19846