Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins
Ismiyarto,; Kishi, Nobuki; Adachi, Yuki; Jiang, Rui; Doi, Takahiro; Zhou, Da-Yang; Asano, Kaori; Obora, Yasushi; Suzuki, Takayoshi; Sasai, Hiroaki; Suzuki, Takeyuki; RSC Advances 11 (2021) 11606–11609; doi:10.1039/D1RA00915J

data_7242499
_publ_section_title
;
 Catalytic enantioselective intramolecular Tishchenko reaction of
 meso-dialdehyde: synthesis of (S)-cedarmycins
;
_journal_issue                   19
_journal_name_full               'RSC Advances'
_journal_page_first              11606
_journal_page_last               11609
_journal_paper_doi               10.1039/D1RA00915J
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety
'(C72 H48 N24 Zn6 I12), 2(C19 H20 O4), 2.5(C1 H2 Cl2)'
_chemical_formula_sum            'C112.5 H93 Cl5 I12 N24 O8 Zn6'
_chemical_formula_weight         4001.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-07-28 deposited with the CCDC.	2021-03-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.5970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.9669(3)
_cell_length_b                   14.81360(10)
_cell_length_c                   30.7587(2)
_cell_measurement_reflns_used    97276
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      79.3690
_cell_measurement_theta_min      2.5680
_cell_volume                     15607.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.954
_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     78.00 143.00   0.50    1.23    --   53.80  77.00-150.00  130
  2  \w      7.00  47.00   0.50    1.23    --   53.80 -77.00 -90.00   80
  3  \w     35.00  71.00   0.50    1.23    --   53.80 -57.00 120.00   72
  4  \w    -24.00  38.00   0.50    1.23    --   53.80 -19.00 -30.00  124
  5  \w    -34.00  71.00   0.50    1.23    --   53.80 -38.00 -90.00  210
  6  \w     53.00  79.00   0.50    1.23    --   53.80 -77.00 -90.00   52
  7  \w     76.00 118.00   0.50    1.23    --   53.80  77.00-180.00   84
  8  \w     23.00 140.00   0.50    4.92    --  108.00 -82.00-120.00  234
  9  \w    150.00 193.00   0.50    4.92    --  108.00  57.00 150.00   86
 10  \w     70.00  95.00   0.50    4.92    --  108.00 -57.00-180.00   50
 11  \w     19.00 129.00   0.50    4.92    --  108.00 -19.00 -30.00  220
 12  \w    169.00 196.00   0.50    4.92    --  108.00  57.00 -60.00   54
 13  \w     85.00 113.00   0.50    4.92    --  108.00  57.00 -60.00   56
 14  \w     34.00  99.00   0.50    4.92    --  108.00 -57.00-120.00  130
 15  \w     26.00  64.00   0.50    4.92    --  108.00 -57.00-180.00   76
 16  \w    115.00 196.00   0.50    4.92    --  108.00  38.00 120.00  162
 17  \w    172.00 197.00   0.50    4.92    --  108.00  38.00  60.00   50
 18  \w     35.00 143.00   0.50    1.23    --   53.80  38.00 -30.00  216
 19  \w     30.00 143.00   0.50    1.23    --   53.80  57.00 120.00  226
 20  \w     30.00 143.00   0.50    1.23    --   53.80  57.00-150.00  226
 21  \w    -36.00  86.00   0.50    1.23    --   53.80 -82.00 120.00  244
 22  \w     81.00 143.00   0.50    1.23    --   53.80  82.00 -30.00  124
 23  \w     30.00  55.00   0.50    1.23    --   53.80  57.00 -90.00   50
 24  \w     30.00 143.00   0.50    1.23    --   53.80  57.00  30.00  226
 25  \w     30.00 143.00   0.50    1.23    --   53.80  57.00 -30.00  226
 26  \w     30.00 143.00   0.50    1.23    --   53.80  57.00 150.00  226
 27  \w    -36.00  84.00   0.50    1.23    --   53.80 -77.00  60.00  240
 28  \w     30.00 143.00   0.50    1.23    --   53.80  57.00 -60.00  226
 29  \w    -36.00  72.00   0.50    1.23    --   53.80 -38.00 120.00  216
 30  \w     30.00 143.00   0.50    1.23    --   53.80  57.00-120.00  226
 31  \w     81.00 143.00   0.50    1.23    --   53.80  82.00  30.00  124
 32  \w     30.00 143.00   0.50    1.23    --   53.80  57.00   0.00  226
 33  \w     35.00 143.00   0.50    1.23    --   53.80  38.00-120.00  216
 34  \w     30.00 143.00   0.50    1.23    --   53.80  57.00  60.00  226
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0169815000
_diffrn_orient_matrix_UB_12      0.0339898000
_diffrn_orient_matrix_UB_13      0.0472628000
_diffrn_orient_matrix_UB_21      -0.0059309000
_diffrn_orient_matrix_UB_22      -0.0943788000
_diffrn_orient_matrix_UB_23      0.0186684000
_diffrn_orient_matrix_UB_31      0.0412160000
_diffrn_orient_matrix_UB_32      -0.0275232000
_diffrn_orient_matrix_UB_33      -0.0055820000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            320208
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.472
_diffrn_reflns_theta_min         2.580
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    20.865
_exptl_absorpt_correction_T_max  0.156
_exptl_absorpt_correction_T_min  0.005
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.703
_exptl_crystal_description       rod
_exptl_crystal_F_000             7604
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.057
_refine_diff_density_max         1.993
_refine_diff_density_min         -1.209
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.225
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1690
_refine_ls_number_reflns         32630
_refine_ls_number_restraints     923
_refine_ls_restrained_S_all      1.216
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0884
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2857
_refine_ls_wR_factor_ref         0.3029
_reflns_Friedel_coverage         0.000
_reflns_number_gt                25738
_reflns_number_total             32630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra00915j2.cif
_cod_data_source_block           lot190304-5_6-hexane-190508-ts-x222-3
_cod_database_code               7242499
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Zn I'
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 O(H) groups
2. Restrained distances
 C113-C112 \\sim C107-C106
 with sigma of 0.02
 C112-C111 \\sim C106-C105
 with sigma of 0.02
 C111-C110 \\sim C105-C104
 with sigma of 0.02
 C110-C109 \\sim C104-C103
 with sigma of 0.02
 C113-C111 \\sim C107-C105
 with sigma of 0.04
 C113-C109 \\sim C107-C103
 with sigma of 0.04
 C112-C110 \\sim C106-C104
 with sigma of 0.04
 C111-C109 \\sim C105-C103
 with sigma of 0.04
 Zn6-I12 \\sim Zn6-I12A
 with sigma of 0.02
 Zn6-I11 \\sim Zn6-I11A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C73 \\sim Cl1 \\sim Cl2: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
C74 \\sim Cl4 \\sim Cl3: within 2A with sigma of 0.04 and sigma for terminal
atoms of 0.08
O5 \\sim C108 \\sim C114 \\sim O6 \\sim C96 \\sim C113 \\sim C117 \\sim C97
\\sim C116 \\sim C115 \\sim C98 \\sim C100 \\sim C119 \\sim O7 \\sim C99 \\sim
C110 \\sim O8: within 1.7A with sigma of 0.04 and sigma for terminal atoms of
0.08
C82 \\sim O2 \\sim C76 \\sim C92 \\sim O1 \\sim C77 \\sim C83 \\sim C91 \\sim
C89 \\sim C78 \\sim C88 \\sim C84 \\sim C90 \\sim C93 \\sim C79 \\sim C81 \\sim
C87 \\sim C85 \\sim C94 \\sim O3 \\sim C80 \\sim C86 \\sim O4: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C111 \\sim C108 \\sim C113 \\sim C109 \\sim C112 \\sim C110: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.01
Cl5 \\sim C75 \\sim Cl6: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.01
C108 \\sim C113 \\sim C112 \\sim C111 \\sim C110 \\sim C109 \\sim C103 \\sim
C102 \\sim C107 \\sim C106 \\sim C105 \\sim C104: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.01
C97 \\sim O5 \\sim C114 \\sim C95 \\sim C115 \\sim O6 \\sim C96 \\sim C102
\\sim C116 \\sim C118 \\sim C117 \\sim C101 \\sim C103 \\sim C107 \\sim C119
\\sim O7 \\sim C98 \\sim C100 \\sim C104 \\sim C106 \\sim O8 \\sim C99 \\sim
C105: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O2, C76, C92, O1, C77, C83, C91, C89, C78, C82, C88, C84, C90, C93, C79, C81,
 C87, C85, C94, O3, C80, C86, O4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 Cl6, C75, Cl5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O7, O5, C114, C95, C115, O6, C96, C102, C116, C118, C117, C97, C101, C103,
 C107, C119, C98, C100, C104, C106, O8, C99, C105, C113, C108, C109, C112, C110,
  C111
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(I3A)=Sof(Zn2A)=Sof(I4A)=1-FVAR(1)
 Sof(Zn2)=Sof(I3)=Sof(I4)=FVAR(1)
 Sof(I9A)=Sof(Zn5A)=Sof(I10A)=1-FVAR(2)
 Sof(Zn5)=Sof(I10)=Sof(I9)=FVAR(2)
 Sof(I2A)=Sof(I1A)=1-FVAR(3)
 Sof(I1)=Sof(I2)=FVAR(3)
 Sof(I5A)=Sof(Zn3A)=Sof(I6A)=1-FVAR(4)
 Sof(Zn3)=Sof(I6)=Sof(I5)=FVAR(4)
 Sof(I7A)=Sof(Zn4A)=Sof(I8A)=1-FVAR(5)
 Sof(Zn4)=Sof(I8)=Sof(I7)=FVAR(5)
 Sof(I12A)=Sof(I11A)=1-FVAR(6)
 Sof(I12)=Sof(I11)=FVAR(6)
 Fixed Sof: Cl4(0.5) Cl3(0.5) C74(0.5) H74A(0.5) H74B(0.5) C108(0.5) C113(0.5)
 H113(0.5) C112(0.5) H112(0.5) C111(0.5) H111(0.5) C110(0.5) H110(0.5)
 C109(0.5) H109(0.5) C102(0.5) C107(0.5) H107(0.5) C106(0.5) H106(0.5)
 C105(0.5) H105(0.5) C104(0.5) H104(0.5) C103(0.5) H103(0.5)
6.a Ternary CH refined with riding coordinates:
 C94(H94), C90(H90), C91(H91), C93(H93), C119(H119), C116(H116), C115(H115),
 C118(H118)
6.b Secondary CH2 refined with riding coordinates:
 C92(H92A,H92B), C89(H89A,H89B), C75(H75A,H75B), C73(H73A,H73B), C74(H74A,
 H74B), C117(H11A,H11B), C114(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C14(H14), C4(H4), C64(H64), C63(H63), C56(H56), C55(H55), C15(H15),
 C20(H20), C43(H43), C27(H27), C2(H2), C1(H1), C28(H28), C45(H45), C19(H19),
 C38(H38), C32(H32), C33(H33), C47(H47), C51(H51), C7(H7), C46(H46), C9(H9),
 C50(H50), C29(H29), C69(H69), C37(H37), C68(H68), C6(H6), C59(H59), C60(H60),
 C42(H42), C30(H30), C65(H65), C61(H61), C48(H48), C10(H10), C41(H41), C22(H22),
  C12(H12), C40(H40), C11(H11), C23(H23), C66(H66), C58(H58), C25(H25),
 C24(H24), C80(H80), C81(H81), C88(H88), C78(H78), C82(H82), C86(H86), C79(H79),
  C84(H84), C85(H85), C87(H87), C101(H101), C100(H100), C99(H99), C98(H98),
 C97(H97), C113(H113), C112(H112), C111(H111), C110(H110), C109(H109),
 C107(H107), C106(H106), C105(H105), C104(H104), C103(H103)
6.d Fitted hexagon refined as free rotating group:
 C96(C101,C100,C99,C98,C97), C108(C113,C112,C111,C110,C109), C102(C107,C106,
 C105,C104,C103)
6.e Tetrahedral OH refined with riding coordinates:
 O3(H3), O4(H4A), O8(H8), O7(H7A)
;
_olex2_date_sample_data_collection 2019-05-08
_olex2_exptl_crystal_mounting_method 'attaced to a capton film'
_olex2_submission_original_sample_id TS-X222
_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 1.835
_oxdiff_exptl_absorpt_empirical_full_min 0.573