Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery and Biomimetic Synthesis.
Li, Wan Shan; Wu, Jun; Li, Jun; Satyanandamurty, Tirumani; Shen, Li; Bringmann, Gerhard; Organic letters  (2016) –; doi:10.1021/acs.orglett.6b03479

data_1544955
_publ_section_title
;
 Krishnadimer A, an Axially Chiral Non-biaryl Natural Product: Discovery
 and Biomimetic Synthesis.
;
_journal_name_full               'Organic letters'
_journal_paper_doi               10.1021/acs.orglett.6b03479
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C70 H86 O22, 2(C H Cl3)'
_chemical_formula_sum            'C72 H88 Cl6 O22'
_chemical_formula_weight         1518.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-06-13
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.38343(14)
_cell_length_b                   17.46463(15)
_cell_length_c                   23.5998(2)
_cell_measurement_reflns_used    39563
_cell_measurement_temperature    294.10(10)
_cell_measurement_theta_max      66.9400
_cell_measurement_theta_min      3.1220
_cell_volume                     7164.79(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.10(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -18.00   61.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000   30.0000 79

  2 omega   13.00   67.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938  -38.0000 -150.0000 54

  3 omega   15.00  107.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   38.0000   60.0000 92

  4 omega   20.00   95.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000  -30.0000 75

  5 omega   74.00  105.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000   60.0000 31

  6 omega  118.00  160.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000   60.0000 42

  7 omega   27.00   53.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -30.0000 26

  8 omega  124.00  154.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 30

  9 omega   62.00  101.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 39

 10 omega  115.00  141.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000 -180.0000 26

 11 omega   38.00   75.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -23.0000  144.2713 37

 12 omega    9.00   34.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000 -149.4871 25

 13 omega   97.00  130.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000 -149.4871 33

 14 omega   16.00   58.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000    0.0000 42

 15 omega   35.00   63.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 28

 16 omega   57.00   83.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

 17 omega   71.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -120.0000 25

 18 omega  106.00  134.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -120.0000 28

 19 omega  142.00  167.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -120.0000 25

 20 omega   84.00  112.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   74.0000   57.2773 28

 21 omega  134.00  160.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   74.0000   57.2773 26

 22 omega   35.00   96.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000 -120.0000 61

 23 omega   28.00   60.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 32

 24 omega   99.00  124.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 25

 25 omega   66.00  153.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000    0.0000 87

 26 omega   73.00  102.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   59.0000   17.7644 29

 27 omega  109.00  167.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   59.0000   17.7644 58

 28 omega   65.00   91.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -65.0000  -87.6098 26

 29 omega   41.00   67.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -60.0000 26

 30 omega   92.00  151.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -15.0000  -60.0000 59

 31 omega   20.00   51.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 31

 32 omega   67.00  110.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 43

 33 omega   12.00   38.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -150.0000 26

 34 omega   38.00   82.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000 -120.0000 44

 35 omega   21.00   47.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 26

 36 omega   92.00  121.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -59.0000  134.0087 29

 37 omega  117.00  143.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000    0.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0571668000
_diffrn_orient_matrix_UB_12      0.0543930000
_diffrn_orient_matrix_UB_13      -0.0294552000
_diffrn_orient_matrix_UB_21      -0.0305718000
_diffrn_orient_matrix_UB_22      0.0258631000
_diffrn_orient_matrix_UB_23      0.0581952000
_diffrn_orient_matrix_UB_31      0.0604418000
_diffrn_orient_matrix_UB_32      0.0645019000
_diffrn_orient_matrix_UB_33      0.0014774000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            66888
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         3.15
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.828
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3192
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.384
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.001(10)
_refine_ls_extinction_coef       0.00008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     943
_refine_ls_number_reflns         12540
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+2.7221P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                11993
_reflns_number_total             12540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03479_si_004.cif
_cod_data_source_block           exp_compound2b
_cod_original_cell_volume        7164.80(11)
_cod_database_code               1544955
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.027) H5(0.025) H6A(0.032) H6B(0.032) H9(0.024) H11A(0.028)
 H11B(0.028) H12A(0.029) H12B(0.029) H17(0.03) H18A(0.036) H18B(0.036)
 H18C(0.036) H19A(0.04) H19B(0.04) H19C(0.04) H21(0.06) H22(0.047) H23(0.05)
 H28A(0.046) H28B(0.046) H28C(0.046) H29A(0.03) H29B(0.03) H31A(0.076)
 H31B(0.076) H31C(0.076) H33(0.034) H34A(0.05) H34B(0.05) H34C(0.05) H35A(0.07)
 H35B(0.07) H35C(0.07) H37(0.037) H38A(0.084) H38B(0.084) H38C(0.084)
 H39A(0.071) H39B(0.071) H39C(0.071) H3'(0.03) H5'(0.03) H6'A(0.037)
 H6'B(0.037) H9'(0.03) H11C(0.036) H11D(0.036) H12C(0.029) H12D(0.029)
 H17'(0.03) H18D(0.039) H18E(0.039) H18F(0.039) H19D(0.052) H19E(0.052)
 H19F(0.052) H21'(0.048) H22'(0.052) H23'(0.052) H28D(0.053) H28E(0.053)
 H28F(0.053) H29C(0.035) H29D(0.035) H31D(0.103) H31E(0.103) H31F(0.103)
 H33'(0.044) H34D(0.071) H34E(0.071) H34F(0.071) H35D(0.075) H35E(0.075)
 H35F(0.075) H37'(0.077) H38D(0.151) H38E(0.151) H38F(0.151) H39D(0.128)
 H39E(0.128) H39F(0.128) H40(0.092) H40'(0.043) H41(0.052) H2(0.044) H7(0.041)
 H2'(0.051) H7'(0.04)
 Fixed X: H3(-0.0438) H5(-0.1122) H6A(-0.2423) H6B(-0.2683) H9(-0.0624) H11A(-
 0.0961) H11B(-0.1455) H12A(-0.0614) H12B(-0.0383) H17(0.1027) H18A(0.0011)
 H18B(0.0896) H18C(0.0233) H19A(-0.1726) H19B(-0.2177) H19C(-0.229) H21(0.1447)
 H22(-0.002) H23(-0.0036) H28A(-0.1718) H28B(-0.2382) H28C(-0.1678) H29A(-
 0.1358) H29B(-0.2043) H31A(-0.1484) H31B(-0.2135) H31C(-0.2361) H33(0.0436)
 H34A(0.1714) H34B(0.1573) H34C(0.1613) H35A(-0.0424) H35B(0.0277) H35C(0.0233)
 H37(-0.0761) H38A(0.0386) H38B(0.0242) H38C(0.0406) H39A(-0.1643) H39B(-
 0.1028) H39C(-0.0869) H3'(0.3555) H5'(0.4345) H6'A(0.569) H6'B(0.5898)
 H9'(0.3963) H11C(0.442) H11D(0.4763) H12C(0.3628) H12D(0.3943) H17'(0.2258)
 H18D(0.3475) H18E(0.2604) H18F(0.327) H19D(0.5047) H19E(0.5498) H19F(0.5557)
 H21'(0.2032) H22'(0.3317) H23'(0.3438) H28D(0.4877) H28E(0.5574) H28F(0.4913)
 H29C(0.4471) H29D(0.5203) H31D(0.6939) H31E(0.6138) H31F(0.6156) H33'(0.2295)
 H34D(0.2488) H34E(0.2392) H34F(0.3228) H35D(0.3242) H35E(0.3695) H35F(0.2859)
 H37'(0.3301) H38D(0.3131) H38E(0.3351) H38F(0.3986) H39D(0.4207) H39E(0.4493)
 H39F(0.4851) H40(0.2167) H40'(0.1942) H41(0.3997) H2(0.0343) H7(0.1068)
 H2'(0.2799) H7'(0.1924)
 Fixed Y: H3(1.1357) H5(1.0146) H6A(0.9511) H6B(1.0184) H9(0.8349)
 H11A(0.8093) H11B(0.8865) H12A(0.8851) H12B(0.9544) H17(0.9608) H18A(0.7534)
 H18B(0.7564) H18C(0.7698) H19A(0.8381) H19B(0.8636) H19C(0.9105) H21(0.8179)
 H22(0.9932) H23(0.9585) H28A(1.1868) H28B(1.1371) H28C(1.1685) H29A(1.071)
 H29B(1.0189) H31A(1.1103) H31B(1.1593) H31C(1.0827) H33(1.2414) H34A(1.2088)
 H34B(1.2076) H34C(1.1289) H35A(1.1498) H35B(1.092) H35C(1.1705) H37(0.7998)
 H38A(0.8217) H38B(0.912) H38C(0.8642) H39A(0.8311) H39B(0.8877) H39C(0.7974)
 H3'(1.1394) H5'(1.036) H6'A(0.9819) H6'B(1.0477) H9'(0.846) H11C(0.8317)
 H11D(0.9167) H12C(0.9657) H12D(0.8986) H17'(0.9518) H18D(0.7634) H18E(0.7532)
 H18F(0.7693) H19D(0.8501) H19E(0.8863) H19F(0.9255) H21'(0.7903) H22'(0.9812)
 H23'(0.9252) H28D(1.1943) H28E(1.1499) H28F(1.1881) H29C(1.0689) H29D(1.0245)
 H31D(1.1643) H31E(1.1362) H31F(1.2067) H33'(1.2152) H34D(1.0841) H34E(1.1303)
 H34F(1.1035) H35D(1.3059) H35E(1.2415) H35F(1.2683) H37'(0.8157) H38D(0.8761)
 H38E(0.7881) H38F(0.8533) H39D(0.7226) H39E(0.7677) H39F(0.7877) H40(0.5514)
 H40'(0.5519) H41(1.3189) H2(1.0017) H7(1.0478) H2'(0.9906) H7'(0.9965)
 Fixed Z: H3(0.3047) H5(0.1998) H6A(0.1956) H6B(0.2372) H9(0.2555)
 H11A(0.1695) H11B(0.1686) H12A(0.0901) H12B(0.1313) H17(0.1073) H18A(0.1466)
 H18B(0.1279) H18C(0.0819) H19A(0.3046) H19B(0.2486) H19C(0.3062) H21(-0.0009)
 H22(0.0209) H23(-0.0793) H28A(0.2908) H28B(0.2615) H28C(0.2244) H29A(0.3645)
 H29B(0.3376) H31A(0.0513) H31B(0.0827) H31C(0.0494) H33(0.1616) H34A(0.1842)
 H34B(0.1172) H34C(0.1518) H35A(0.1252) H35B(0.1151) H35C(0.0802) H37(0.4286)
 H38A(0.4793) H38B(0.4758) H38C(0.4193) H39A(0.5001) H39B(0.5282) H39C(0.5269)
 H3'(0.139) H5'(0.2476) H6'A(0.2561) H6'B(0.2114) H9'(0.2055) H11C(0.2899)
 H11D(0.2889) H12C(0.328) H12D(0.3681) H17'(0.3582) H18D(0.3026) H18E(0.3233)
 H18F(0.3685) H19D(0.1561) H19E(0.2088) H19F(0.1476) H21'(0.4532) H22'(0.4462)
 H23'(0.5407) H28D(0.1391) H28E(0.1689) H28F(0.2067) H29C(0.0797) H29D(0.1071)
 H31D(0.3575) H31E(0.3838) H31F(0.3405) H33'(0.2822) H34D(0.2985) H34E(0.3566)
 H34F(0.3362) H35D(0.3067) H35E(0.3415) H35F(0.3618) H37'(0.0418) H38D(-0.045)
 H38E(-0.0546) H38F(-0.0636) H39D(0.014) H39E(0.0692) H39F(0.0084) H40(0.0281)
 H40'(0.028) H41(0.1404) H2(0.375) H7(0.2867) H2'(0.0832) H7'(0.2174)
;
_olex2_submission_special_instructions 'No special instructions were received'