Cyclic (Aryl)(Amido)carbenes: Pushing the π-Acidity of Amidocarbenes Through Benzannulation
Gildner, M. Brenton; Hudnall, Todd W.; Chemical Communications  (2019) –; doi:10.1039/C9CC05280A

data_7124232
_publ_section_title
;
 Cyclic (Aryl)(Amido)carbenes: Pushing the \p-Acidity of Amidocarbenes
 Through Benzannulation
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC05280A
_journal_year                    2019
_chemical_formula_moiety         'C34 H30 N2 O2'
_chemical_formula_sum            'C34 H30 N2 O2'
_chemical_formula_weight         498.60
_chemical_name_common            'Mes-camary dimer'
_chemical_name_systematic        N-mesityl-isoindolinon-2-yl-dimer
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-07-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-08 deposited with the CCDC.    2019-09-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.77(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.941(2)
_cell_length_b                   16.435(3)
_cell_length_c                   15.416(3)
_cell_measurement_reflns_used    4713
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      25.000
_cell_measurement_theta_min      3.001
_cell_volume                     2680.4(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.30d (Rigaku OD, 2017)'
_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    'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21657
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.001
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_description       prism
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         4713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1164
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+1.1541P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1402
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2752
_reflns_number_total             4713
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05280a2.cif
_cod_data_source_block           5a
_cod_original_cell_volume        2680.3(10)
_cod_database_code               7124232
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C16(H16), C19(H19), C20(H20), C24(H24), C25(H25),
 C26(H26), C30(H30), C32(H32), C33(H33), C34(H34)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C29(H29A,H29B,H29C), C31(H31A,H31B,H31C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              42961
_olex2_submission_special_instructions 'No special instructions were received'