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_4519302
_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         'C28 H37 N O3'
_chemical_formula_sum            'C28 H37 N O3'
_chemical_formula_weight         435.58
_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             2021-05-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.2805(5)
_cell_length_b                   9.5063(2)
_cell_length_c                   18.9097(3)
_cell_measurement_reflns_used    13453
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.5320
_cell_measurement_theta_min      3.2340
_cell_volume                     4898.04(16)
_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      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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     31.00 119.00   0.50    1.57    --   46.75  53.00 -20.00  176
  2  \w     91.00 178.00   0.50    6.27    --  106.69  53.00 -20.00  174
  3  \w     92.00 169.00   0.50    6.27    --  106.69  61.00  30.00  154
  4  \w     92.00 176.00   0.50    6.27    --  106.69  61.00  55.48  168
  5  \w     94.00 129.00   0.50    6.27    --  106.69  61.00  90.00   70
  6  \w     34.00  71.00   0.50    6.27    --  106.69 -61.00  30.00   74
  7  \w     39.00  65.00   0.50    6.27    --  106.69 -61.00 -30.00   52
  8  \w     56.00  93.00   0.50    6.27    --  106.69 -77.00 -60.00   74
  9  \w     39.00  70.00   0.50    6.27    --  106.69 -61.00 -90.00   62
 10  \w     34.00  60.00   0.50    6.27    --  106.69 -53.00-165.00   52
 11  \w     34.00 105.00   0.50    6.27    --  106.69 -94.00-120.00  142
 12  \w     76.00 108.00   0.50    6.27    --  106.69-125.00-150.00   64
 13  \w     35.00  74.00   0.50    6.27    --  106.69-125.00-150.00   78
 14  \w     34.00  71.00   0.50    6.27    --  106.69 -61.00-120.00   74
 15  \w     92.00 176.00   0.50    6.27    --  106.69  30.00 -90.00  168
 16  \w     33.00 120.00   0.50    1.57    --   46.75  43.00 104.81  174
 17  \w     38.00  65.00   0.50    6.27    --  106.69 -61.00  60.00   54
 18  \w     35.00 101.00   0.50    6.27    --  106.69 -77.00 120.00  132
 19  \w    -25.00  60.00   0.50    1.57    --   46.75 -53.00-165.00  170
 20  \w    -60.00  26.00   0.50    1.57    --  -46.75  53.00 -20.00  172
 21  \w    -51.00 -16.00   0.50    6.27    --  -88.50  45.00 120.00   70
 22  \w    -51.00 -16.00   0.50    6.27    --  -88.50  45.00  90.00   70
 23  \w    -51.00 -16.00   0.50    6.27    --  -88.50  45.00 150.00   70
 24  \w    -60.00 -15.00   0.50    6.27    --  -88.50  53.00 -20.00   90
 25  \w    -71.00 -15.00   0.50    6.27    --  -88.50  61.00-120.00  112
 26  \w    -51.00 -16.00   0.50    6.27    --  -88.50  45.00-180.00   70
 27  \w    -71.00 -15.00   0.50    6.27    --  -88.50  61.00 -60.00  112
 28  \w   -119.00 -31.00   0.50    1.57    --  -46.75 -53.00-165.00  176
 29  \w   -119.00 -88.00   0.50    1.57    --  -46.75-125.00 -30.00   62
 30  \w   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00-165.00  174
 31  \w   -160.00-100.00   0.50    6.27    --  -88.50 -94.00 -60.00  120
 32  \w   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00  74.71  174
 33  \w   -160.00 -73.00   0.50    6.27    --  -88.50 -55.00  58.36  174
 34  \w   -160.00 -91.00   0.50    6.27    --  -88.50 -61.00 150.00  138
 35  \w   -161.00 -74.00   0.50    6.27    --  -88.50 -45.00  60.00  174
 36  \w   -163.00 -73.00   0.50    6.27    --  -88.50 -30.00  90.00  180
 37  \w   -160.00 -78.00   0.50    6.27    --  -88.50 -56.00 118.89  164
 38  \w   -160.00 -72.00   0.50    6.27    --  -88.50 -51.00  37.38  176
 39  \w   -160.00 -72.00   0.50    6.27    --  -88.50 -54.00  93.30  176
 40  \w   -160.00 -73.00   0.50    6.27    --  -88.50 -53.00 138.71  174
;
_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      -0.0529935000
_diffrn_orient_matrix_UB_12      -0.0060218000
_diffrn_orient_matrix_UB_13      -0.0319697000
_diffrn_orient_matrix_UB_21      0.0162807000
_diffrn_orient_matrix_UB_22      -0.1043169000
_diffrn_orient_matrix_UB_23      -0.0567102000
_diffrn_orient_matrix_UB_31      -0.0110703000
_diffrn_orient_matrix_UB_32      -0.1239304000
_diffrn_orient_matrix_UB_33      0.0491254000
_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  0.0663
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            43511
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.876
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.797
_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    1.181
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.167
_exptl_crystal_size_mid          0.052
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5004
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0663
_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^)+(0.0300P)^2^+9.5000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1482
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4337
_reflns_number_total             5004
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs1c05611_si_002.cif
_cod_data_source_block           hpd335a
_cod_database_code               4519302
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     7-25-7-1
_reflns_odcompleteness_completeness 99.94
_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.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C15(H15A,H15B), C20(H20A,H20B), C22(H22A,H22B), C16(H16A,
 H16B), C23(H23A,H23B), C24(H24A,H24B), C27(H27A,H27B), C25(H25A,H25B),
 C28(H28A,H28B), C26(H26A,H26B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3A), C6(H6), C4(H4), C9(H9), C5(H5), C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              94451
_shelx_hkl_checksum              6358
_olex2_exptl_crystal_mounting_method 'nylon 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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.125
_oxdiff_exptl_absorpt_empirical_full_min 0.583