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_7125705
_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         'C22 H20 F2 N2 O4'
_chemical_formula_sum            'C22 H20 F2 N2 O4'
_chemical_formula_weight         414.40
_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   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                 105.347(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.6617(14)
_cell_length_b                   9.8335(5)
_cell_length_c                   12.6100(9)
_cell_measurement_reflns_used    1967
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      24.9560
_cell_measurement_theta_min      4.1910
_cell_volume                     1992.4(3)
_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 0.848
_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      1.00  83.00   1.00    7.50    --   15.49  57.00  30.00   82
  2  \w     35.00  60.00   1.00    7.50    --   15.49 178.00-180.00   25
  3  \w    -49.00  42.00   1.00    7.50    --   15.49 -77.00-120.00   91
  4  \w    -19.00   8.00   1.00    7.50    --  -16.12 -99.00  30.00   27
;
_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      -0.0406586000
_diffrn_orient_matrix_UB_12      -0.0037742000
_diffrn_orient_matrix_UB_13      -0.0360731000
_diffrn_orient_matrix_UB_21      0.0068030000
_diffrn_orient_matrix_UB_22      -0.0692290000
_diffrn_orient_matrix_UB_23      -0.0108836000
_diffrn_orient_matrix_UB_31      -0.0158879000
_diffrn_orient_matrix_UB_32      -0.0199847000
_diffrn_orient_matrix_UB_33      0.0444779000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9755
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.262
_diffrn_reflns_theta_min         3.628
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54690
_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    1.382
_exptl_crystal_description       plate
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4601
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1145
_refine_ls_R_factor_gt           0.0609
_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^)+(0.0670P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1262
_refine_ls_wR_factor_ref         0.1623
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2577
_reflns_number_total             4601
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07372h2.cif
_cod_data_source_block           syn-3l
_cod_depositor_comments
'Adding full bibliography for 7125703--7125707.cif.'
_cod_database_code               7125705
_shelx_shelxl_version_number     2018/1
_reflns_odcompleteness_completeness 99.58
_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
 C9-C8 \\sim C9B-C8
 with sigma of 0.01
 C9B-C10B \\sim C9-C10
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C9) \\sim Ueq, Uanis(C9B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C10) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Sof(H8B)=Sof(C10B)=Sof(H10C)=Sof(H10D)=Sof(C9B)=Sof(H9B)=1-FVAR(1)
 Sof(H8A)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8A), C8(H8B), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C9(H9), C16(H16), C14(H14), C13(H13), C19(H19),
 C9B(H9B)
5.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C20(H20A,H20B), C10B(H10C,H10D)
;
_shelx_res_checksum              65036
_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 3.038
_oxdiff_exptl_absorpt_empirical_full_min 0.652