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_7125707
_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         '2(C11 H11 N O2)'
_chemical_formula_sum            'C22 H22 N2 O4'
_chemical_formula_weight         378.41
_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   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                 99.915(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5996(10)
_cell_length_b                   8.1161(5)
_cell_length_c                   16.4481(14)
_cell_measurement_reflns_used    2229
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      25.1780
_cell_measurement_theta_min      3.7760
_cell_volume                     1919.9(2)
_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 0.997
_diffrn_measured_fraction_theta_max 0.855
_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    -51.00 -20.00   1.00    7.50    --  -16.12 -57.00 -30.00   31
  2  \w    -84.00  52.00   1.00    7.50    --  -16.12   0.00   0.00  136
  3  \w    -10.00  36.00   1.00    7.50    --   15.49 -77.00 150.00   46
  4  \w     11.00  51.00   1.00    7.50    --  -16.12  57.00-180.00   40
;
_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      0.0064892000
_diffrn_orient_matrix_UB_12      0.0143595000
_diffrn_orient_matrix_UB_13      0.0431566000
_diffrn_orient_matrix_UB_21      -0.0413373000
_diffrn_orient_matrix_UB_22      -0.0444118000
_diffrn_orient_matrix_UB_23      0.0022615000
_diffrn_orient_matrix_UB_31      0.0261086000
_diffrn_orient_matrix_UB_32      -0.0738517000
_diffrn_orient_matrix_UB_33      0.0070485000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0686
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10170
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.332
_diffrn_reflns_theta_min         3.449
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43188
_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    1.309
_exptl_crystal_description       prism
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0564
_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^)+(0.0508P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1421
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2192
_reflns_number_total             4506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07372h2.cif
_cod_data_source_block           anti-3a
_cod_depositor_comments
'Adding full bibliography for 7125703--7125707.cif.'
_cod_database_code               7125707
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.60
_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
2. Restrained distances
 C21B-C20B \\sim C21-C20
 with sigma of 0.01
 C20-C19 \\sim C20B-C19
 with sigma of 0.01
3. Others
 Sof(H19A)=Sof(C20B)=Sof(H20B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=1-FVAR(1)
 Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21A)=Sof(H21B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C19(H19), C19(H19A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C20B(H20B)
4.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C21(H21A,H21B), C21B(H21C,H21D)
;
_shelx_res_checksum              96324
_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 2.216
_oxdiff_exptl_absorpt_empirical_full_min 0.562