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_1569160
_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         'C53 H61 N5 O4'
_chemical_formula_sum            'C53 H61 N5 O4'
_chemical_formula_weight         832.06
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2021-12-24
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2022-08-16 deposited with the CCDC.	2023-05-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.1817(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6441(2)
_cell_length_b                   13.8612(2)
_cell_length_c                   25.1810(5)
_cell_measurement_reflns_used    12942
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3800
_cell_measurement_theta_min      3.5680
_cell_volume                     4636.84(14)
_computing_cell_refinement       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -36.00  27.00   0.50   12.00    --   -5.92   0.00 150.00  126
  2  \w    -56.00  13.00   0.50   12.00    --    5.92 -37.00 150.00  138
  3  \w    -64.00 -13.00   0.50   50.00    --  -84.25  37.00 120.00  102
  4  \w    -52.00 -26.00   0.50   50.00    --  -84.25  19.00  90.00   52
  5  \w    -47.00   6.00   0.50   12.00    --    5.92 -77.00-120.00  106
  6  \w     35.00 115.00   0.50   50.00    --  105.75 -57.00  30.00  160
  7  \w    151.00 178.00   0.50   50.00    --  105.75  19.00 120.00   54
  8  \w    111.00 175.00   0.50   50.00    --  105.75  86.00 155.00  128
  9  \w    105.00 136.00   0.50   50.00    --  105.75  19.00 120.00   62
 10  \w     98.00 146.00   0.50   50.00    --  105.75  37.00 150.00   96
 11  \w     48.00 127.00   0.50   50.00    --  105.75 -77.00  30.00  158
 12  \w    114.00 140.00   0.50   50.00    --  105.75  19.00 -90.00   52
 13  \w    151.00 178.00   0.50   50.00    --  105.75  19.00 -90.00   54
 14  \w     36.00  62.00   0.50   50.00    --  105.75 -37.00 -60.00   52
 15  \w     35.00  65.00   0.50   50.00    --  105.75 -37.00-120.00   60
 16  \w     38.00  64.00   0.50   50.00    --  105.75 -37.00-150.00   52
 17  \w     33.00  65.00   0.50   50.00    --  105.75 -37.00-180.00   64
 18  \w     37.00  63.00   0.50   50.00    --  105.75 -99.00-180.00   52
 19  \w     33.00  61.00   0.50   50.00    --  105.75 -37.00  30.00   56
 20  \w     36.00  65.00   0.50   50.00    --  105.75 -37.00 120.00   58
 21  \w    -95.00 -15.00   0.50   50.00    --  -84.25 125.00-180.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27365
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         6.287
_diffrn_source                   'Cu PhotonJet-S microsource'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.594
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72811
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.7f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_description       plate
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.121
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.029
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     803
_refine_ls_number_reflns         8177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0683P)^2^+0.9416P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6821
_reflns_number_total             8177
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc05122b2.cif
_cod_data_source_block           tsu_1
_cod_depositor_comments
'Adding full bibliography for 1569160--1569162.cif.'
_cod_database_code               1569160
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
;
_shelx_res_checksum              95179
_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
;