Photochemical reactions of a diamidocarbene: cyclopropanation of bromonaphthalene, addition to pyridine, and activation of sp<sup>3</sup> C-H bonds.
Perera, Tharushi A.; Taylor, William V.; Gildner, M. Brenton; Reinheimer, Eric W.; Ito, Sho; Nelson, Anna; Yost, Shane R.; Hudnall, Todd W.; Chemical science 14 (2023) 7867–7874; doi:10.1039/d2sc05122b

data_1569161
_publ_section_title
;
 Photochemical reactions of a diamidocarbene: cyclopropanation of
 bromonaphthalene, addition to pyridine, and activation of sp<sup>3</sup>
 C-H bonds.
;
_journal_issue                   29
_journal_name_full               'Chemical science'
_journal_page_first              7867
_journal_page_last               7874
_journal_paper_doi               10.1039/d2sc05122b
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C30 H40 N2 O2'
_chemical_formula_sum            'C30 H40 N2 O2'
_chemical_formula_weight         460.66
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-30
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-08-16 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.1(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.56(13)
_cell_length_b                   19.48(12)
_cell_length_c                   15.5(3)
_cell_measurement_reflns_used    1779
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.8710
_cell_measurement_theta_min      0.1170
_cell_volume                     2879(7)
_computing_cell_refinement       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.55a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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    -45.00  50.00   0.25    1.00    --    0.00   0.00   0.00  380
  2  \w    -35.00  75.00   0.25    0.50    --    0.00   0.00   0.00  440
  3  \w    -65.00  23.00   0.25    1.00    --    0.00   0.00   0.00  352
  4  \w    -15.00  60.00   0.25    1.00    --    0.00   0.00   0.00  300
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002066000
_diffrn_orient_matrix_UB_12      0.0001104000
_diffrn_orient_matrix_UB_13      0.0016044000
_diffrn_orient_matrix_UB_21      -0.0023058000
_diffrn_orient_matrix_UB_22      -0.0006113000
_diffrn_orient_matrix_UB_23      -0.0001489000
_diffrn_orient_matrix_UB_31      0.0012393000
_diffrn_orient_matrix_UB_32      -0.0011296000
_diffrn_orient_matrix_UB_33      0.0002211000
_diffrn_radiation_monochromator  'transmission electron microscope'
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.2406
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22427
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        0.749
_diffrn_reflns_theta_max         0.749
_diffrn_reflns_theta_min         0.099
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.06785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.55a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_description       plate
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.002
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.00015
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       85(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   2.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      2.063
_refine_ls_R_factor_all          0.2325
_refine_ls_R_factor_gt           0.1648
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3778
_refine_ls_wR_factor_ref         0.4084
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2054
_reflns_number_total             3387
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05122b2.cif
_cod_data_source_block           3231-3229-3227-3225
_cod_depositor_comments
'Adding full bibliography for 1569160--1569162.cif.'
_cod_original_cell_volume        2879(67)
_cod_database_code               1569161
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C13(H13), C23(H23), C25(H25)
2.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C20(H20A,H20B,H20C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C19(H19A,
 H19B,H19C)
;
_shelx_res_checksum              18462
_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
;