Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds
Su, Yong-Liang; Liu, Geng-Xin; De Angelis, Luca; He, Ru; Al-Sayyed, Ammar; Schanze, Kirk S.; Hu, Wen-Hao; Qiu, Huang; Doyle, Michael P.; ACS Catalysis 12 (2022) 1357–1363; doi:10.1021/acscatal.1c05611

data_4519303
_publ_section_title
;
 Radical Cascade Multicomponent Minisci Reactions with Diazo Compounds
;
_journal_issue                   2
_journal_name_full               'ACS Catalysis'
_journal_page_first              1357
_journal_page_last               1363
_journal_paper_doi               10.1021/acscatal.1c05611
_journal_volume                  12
_journal_year                    2022
_chemical_formula_moiety         'C25 H36 N O3'
_chemical_formula_sum            'C25 H36 N O3'
_chemical_formula_weight         398.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-05-17
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.703(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2586(15)
_cell_length_b                   10.3745(7)
_cell_length_c                   18.8315(8)
_cell_measurement_reflns_used    5629
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.7080
_cell_measurement_theta_min      3.6230
_cell_volume                     4729.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -28.00  29.00   0.50    0.88    --   46.62 -13.00 100.00  114
  2  \w     32.00 121.00   0.50    0.88    --   46.62  37.00 120.00  178
  3  \w     34.00  71.00   0.50    3.51    --  106.69 -61.00   0.00   74
  4  \w     34.00 105.00   0.50    3.51    --  106.69 -94.00 -60.00  142
  5  \w     28.00 123.00   0.50    0.88    --   46.62  13.00 -87.00  190
  6  \w     88.00 178.00   0.50    3.51    --  106.69  13.00 -87.00  180
  7  \w     92.00 178.00   0.50    3.51    --  106.69  45.00-180.00  172
  8  \w     34.00  71.00   0.50    3.51    --  106.69 -61.00 -90.00   74
  9  \w     34.00  71.00   0.50    3.51    --  106.69 -61.00-120.00   74
 10  \w     34.00  71.00   0.50    3.51    --  106.69 -61.00-180.00   74
 11  \w     34.00 101.00   0.50    3.51    --  106.69 -77.00-120.00  134
 12  \w     34.00 105.00   0.50    3.51    --  106.69 -94.00   0.00  142
 13  \w     34.00 111.00   0.50    3.51    --  106.69-125.00   0.00  154
 14  \w     34.00 105.00   0.50    3.51    --  106.69 -94.00-180.00  142
 15  \w     34.00  95.00   0.50    0.88    --   46.62-125.00-180.00  122
 16  \w     32.00 121.00   0.50    0.88    --   46.62  37.00-180.00  178
 17  \w     32.00 121.00   0.50    0.88    --   46.62  37.00 -60.00  178
 18  \w     32.00 121.00   0.50    0.88    --   46.62  37.00  30.00  178
 19  \w    -29.00  30.00   0.50    0.88    --  -46.62  13.00 -87.00  118
 20  \w    -30.00  14.00   0.50    0.88    --  -46.62  19.00-150.00   88
 21  \w    -51.00 -16.00   0.50    3.51    --  -88.50  45.00-150.00   70
 22  \w    -51.00 -16.00   0.50    3.51    --  -88.50  45.00 -30.00   70
 23  \w   -123.00 -28.00   0.50    0.88    --  -46.62 -13.00 100.00  190
 24  \w    -27.00  43.00   0.50    0.88    --   46.62 -37.00 -30.00  140
 25  \w   -119.00 -83.00   0.50    0.88    --  -46.62 -57.00 -60.00   72
 26  \w   -119.00 -83.00   0.50    0.88    --  -46.62 -57.00-150.00   72
 27  \w   -160.00 -88.00   0.50    3.51    --  -88.50-125.00-150.00  144
 28  \w   -164.00 -70.00   0.50    3.51    --  -88.50 -13.00 100.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325581000
_diffrn_orient_matrix_UB_12      -0.0263459000
_diffrn_orient_matrix_UB_13      -0.0660485000
_diffrn_orient_matrix_UB_21      0.0542354000
_diffrn_orient_matrix_UB_22      -0.0025386000
_diffrn_orient_matrix_UB_23      0.0472973000
_diffrn_orient_matrix_UB_31      -0.0068190000
_diffrn_orient_matrix_UB_32      -0.1461080000
_diffrn_orient_matrix_UB_33      0.0111910000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25659
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.498
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_min         3.652
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_description       needle
_exptl_crystal_F_000             1736
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.079
_exptl_crystal_size_min          0.064
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4250
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0947
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0050P)^2^+12.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3217
_reflns_number_total             4250
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05611_si_003.cif
_cod_data_source_block           hpd336b
_cod_database_code               4519303
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     7-16-8-2
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2. Others
 Fixed Sof: C23A(0.65) H23A(0.65) H23B(0.65) C24A(0.65) H24A(0.65) H24B(0.65)
 H24C(0.65) C24B(0.35) H24D(0.35) H24E(0.35) H24F(0.35) C23B(0.35) H23C(0.35)
 H23D(0.35)
3.a Ternary CH refined with riding coordinates:
 C10(H10)
3.b Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C14(H14A,H14B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,
 H13B), C21(H21A,H21B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B),
 C17(H17A,H17B), C23A(H23A,H23B), C23B(H23C,H23D)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C6(H6), C19(H19), C7(H7)
3.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C24A(H24A,H24B,H24C), C24B(H24D,H24E,H24F)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              83789
_shelx_hkl_checksum              83214
_olex2_exptl_crystal_mounting_method 'MiTeGen loop'
_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 1.996
_oxdiff_exptl_absorpt_empirical_full_min 0.603