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_7125704
_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 H20 F6 N2 O4'
_chemical_formula_sum            'C24 H20 F6 N2 O4'
_chemical_formula_weight         514.42
_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             2019-11-04
_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                 91.940(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.1630(3)
_cell_length_b                   10.7505(3)
_cell_length_c                   10.3964(3)
_cell_measurement_reflns_used    1608
_cell_measurement_temperature    293.1(2)
_cell_measurement_theta_max      70.7180
_cell_measurement_theta_min      4.3360
_cell_volume                     1135.23(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      293.1(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega -108.00  -38.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 140

  2 omega  -48.00   29.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000  150.0000 154

  3 omega   66.00  106.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  -30.0000 80

  4 omega   58.00   95.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000  150.0000 74

  5 omega   44.00   75.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -99.0000  120.0000 62

  6 omega  -32.00   31.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000  -30.0000 126

  7 omega   35.00   96.00   0.5000    0.5000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -60.0000 122

  8 omega   38.00   72.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 68

  9 omega   65.00   91.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 52

 10 omega   38.00   63.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 50

 11 omega  102.00  161.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 118

 12 omega   91.00  160.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 138

 13 omega   70.00  107.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 74

 14 omega   56.00  126.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -61.0000 -150.0000 140

 15 omega   99.00  173.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000 -180.0000 148

 16 omega   39.00  101.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 124

 17 omega   38.00   85.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   30.0000 94

 18 omega   39.00   80.00   0.5000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -150.0000 82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1420934000
_diffrn_orient_matrix_UB_12      -0.0030533000
_diffrn_orient_matrix_UB_13      0.0566327000
_diffrn_orient_matrix_UB_21      -0.0352486000
_diffrn_orient_matrix_UB_22      -0.1128473000
_diffrn_orient_matrix_UB_23      0.0833889000
_diffrn_orient_matrix_UB_31      0.0399403000
_diffrn_orient_matrix_UB_32      -0.0882739000
_diffrn_orient_matrix_UB_33      -0.1086255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4348
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         4.353
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.505
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2029
_refine_ls_number_restraints     38
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0481
_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^)+(0.0792P)^2^+0.2074P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1455
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1663
_reflns_number_total             2029
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc07372h2.cif
_cod_data_source_block           anti-3m
_cod_depositor_comments
'Adding full bibliography for 7125703--7125707.cif.'
_cod_original_cell_volume        1135.22(6)
_cod_database_code               7125704
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         C21H22N3O3
_shelx_estimated_absorpt_t_max   0.891
_shelx_estimated_absorpt_t_min   0.833
_reflns_odcompleteness_completeness 99.95
_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
2. Restrained distances
 F3A-C11
 1.37 with sigma of 0.02
 C11-F2A
 1.37 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F2A)
\\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F3A) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
4. Others
 Sof(F1A)=Sof(F2A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C8(H8)
5.b Secondary CH2 refined with riding coordinates:
 C0AA(H0AA,H0AB)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C3(H3), C9(H9)
5.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
;
_shelx_res_checksum              43900
_olex2_submission_special_instructions 'No special instructions were received'