Facile access to versatile aza-macrolides through iridium-catalysed cascade allyl-amination/macrolactonization.
Fu, Wei; Wang, Lianhui; Yang, Zi; Shen, Jiang-Shan; Tang, Fei; Zhang, Jiayi; Cui, Xiuling; Chemical communications (Cambridge, England) 56 (2020) 960–963; doi:10.1039/c9cc07372h

data_7125706
_publ_section_title
;
 Facile access to versatile aza-macrolides through iridium-catalysed
 cascade allyl-amination/macrolactonization.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              960
_journal_page_last               963
_journal_paper_doi               10.1039/c9cc07372h
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C24 H26 N2 O6'
_chemical_formula_sum            'C24 H26 N2 O6'
_chemical_formula_weight         438.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2019-11-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-11-04 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.5668(5)
_cell_length_b                   17.1785(9)
_cell_length_c                   23.0513(10)
_cell_measurement_reflns_used    4025
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      24.7610
_cell_measurement_theta_min      3.7180
_cell_volume                     4580.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.875
_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      3.00  83.00   0.80    5.00    --   15.49  57.00 -60.00  100
  2  \w     37.00  72.20   0.80    5.00    --   15.49 178.00   0.00   44
  3  \w    -21.00  22.20   0.80    5.00    --  -16.28 -99.00 120.00   54
  4  \w     56.00  80.80   0.80    5.00    --   15.49-147.00  71.00   31
  5  \w     -2.00  50.00   0.80    5.00    --   15.49-124.00-123.00   65
  6  \w    -21.00   9.40   0.80    5.00    --  -16.28 -99.00-120.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0224015000
_diffrn_orient_matrix_UB_12      -0.0382268000
_diffrn_orient_matrix_UB_13      0.0032334000
_diffrn_orient_matrix_UB_21      -0.0024509000
_diffrn_orient_matrix_UB_22      -0.0052846000
_diffrn_orient_matrix_UB_23      -0.0304831000
_diffrn_orient_matrix_UB_31      0.0569943000
_diffrn_orient_matrix_UB_32      0.0147763000
_diffrn_orient_matrix_UB_33      -0.0025919000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25391
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.492
_diffrn_reflns_theta_min         3.443
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_description       prism
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0608
_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^)+(0.0680P)^2^+0.9273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1341
_refine_ls_wR_factor_ref         0.1672
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3156
_reflns_number_total             5572
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07372h2.cif
_cod_data_source_block           syn-3g
_cod_depositor_comments
'Adding full bibliography for 7125703--7125707.cif.'
_cod_database_code               7125706
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Uiso/Uaniso restraints and constraints
Uanis(C23) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C18(H18)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C9(H9), C13(H13), C15(H15), C16(H16), C19(H19)
3.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B)
3.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              82436
_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 2.169
_oxdiff_exptl_absorpt_empirical_full_min 0.646