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_7124234
_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         'C17 H15 N O Se'
_chemical_formula_sum            'C17 H15 N O Se'
_chemical_formula_weight         328.26
_chemical_name_common            Mesityl-Camary-Selenium
_chemical_name_systematic        2-mesityl-3-selenoxoisoindolin-1-one
_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
_atom_sites_solution_primary     dual
_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                 101.67(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.019(2)
_cell_length_b                   8.6626(17)
_cell_length_c                   17.467(5)
_cell_measurement_reflns_used    2035
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      23.2010
_cell_measurement_theta_min      2.0790
_cell_volume                     1484.6(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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      223(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_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   -120.00  60.00   1.00   20.00    --  -29.30  54.00   0.00  180
  2  \w   -120.00  60.00   1.00   20.00    --  -29.30  54.00 120.00  180
  3  \w   -120.00  60.00   1.00   20.00    --  -29.30  54.00 240.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0693454000
_diffrn_orient_matrix_UB_12      0.0048309000
_diffrn_orient_matrix_UB_13      0.0033352000
_diffrn_orient_matrix_UB_21      0.0183594000
_diffrn_orient_matrix_UB_22      -0.0223995000
_diffrn_orient_matrix_UB_23      0.0398193000
_diffrn_orient_matrix_UB_31      0.0095067000
_diffrn_orient_matrix_UB_32      0.0785285000
_diffrn_orient_matrix_UB_33      0.0110428000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0933
_diffrn_reflns_av_unetI/netI     0.0726
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10958
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.174
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            teal
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.587
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0541
_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^)+(0.0652P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1219
_refine_ls_wR_factor_ref         0.1487
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1652
_reflns_number_total             2526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc05280a2.cif
_cod_data_source_block           7a
_cod_original_cell_volume        1484.7(6)
_cod_database_code               7124234
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C17 H15 N1 O1 Se1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C00C(H00C), C00E(H00E), C00F(H00F), C00G(H00G), C00I(H00K), C00J(H00L)
2.b Idealised Me refined as rotating group:
 C00D(H00A,H00B,H00D), C00H(H00H,H00I,H00J), C00K(H00M,H00N,H00O)
;
_shelx_res_checksum              30490
_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 2.954
_oxdiff_exptl_absorpt_empirical_full_min 0.621