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_1544954
_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         'C62 H74 O20, C1 H2 Cl2, H2 O1, 2(C H4 O)'
_chemical_formula_sum            'C65 H86 Cl2 O23'
_chemical_formula_weight         1306.24
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-24
_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                 93.3670(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.39400(10)
_cell_length_b                   19.6042(2)
_cell_length_c                   14.84510(10)
_cell_measurement_reflns_used    1476
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      3.74
_cell_volume                     3310.23(5)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_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_temperature      150.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            64286
_diffrn_reflns_theta_full        71.66
_diffrn_reflns_theta_max         71.66
_diffrn_reflns_theta_min         2.98
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.533
_exptl_absorpt_correction_T_max  0.6913
_exptl_absorpt_correction_T_min  0.5653
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       0.00020(5)
_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   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     860
_refine_ls_number_reflns         12875
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.122
_refine_ls_R_factor_all          0.1033
_refine_ls_R_factor_gt           0.0989
_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^)+(0.0177P)^2^+12.9174P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2003
_refine_ls_wR_factor_ref         0.2024
_reflns_number_gt                11909
_reflns_number_total             12875
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03479_si_003.cif
_cod_data_source_block           krishnadimerA
_cod_database_code               1544954
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.04) H5(0.047) H6A(0.083) H6B(0.083) H9(0.041) H11A(0.047)
 H11B(0.047) H12A(0.048) H12B(0.048) H17(0.057) H18A(0.065) H18B(0.065)
 H18C(0.065) H19A(0.069) H19B(0.069) H19C(0.069) H21(0.115) H22(0.126)
 H23(0.145) H28A(0.085) H28B(0.085) H28C(0.085) H29A(0.048) H29B(0.048)
 H31A(0.269) H31B(0.269) H31C(0.269) H33(0.08) H34A(0.174) H34B(0.174)
 H34C(0.174) H35A(0.224) H35B(0.224) H35C(0.224) H1(0.06) H2(0.056) H7(0.057)
 H3'(0.051) H5'(0.056) H6'A(0.073) H6'B(0.073) H9'(0.053) H11C(0.074)
 H11D(0.074) H12C(0.075) H12D(0.075) H17'(0.074) H18D(0.065) H18E(0.065)
 H18F(0.065) H19D(0.077) H19E(0.077) H19F(0.077) H21'(0.155) H22'(0.106)
 H23'(0.112) H28D(0.091) H28E(0.091) H28F(0.091) H29C(0.058) H29D(0.058)
 H31D(0.207) H31E(0.207) H31F(0.207) H33'(0.127) H34D(0.219) H34E(0.219)
 H34F(0.219) H35D(0.238) H35E(0.238) H35F(0.238) H1'(0.063) H2'(0.06)
 H7'(0.065) 
 Fixed X: H3(-0.4343) H5(-0.2043) H6A(-0.1045) H6B(-0.2094) H9(0.0428)
 H11A(0.1122) H11B(-0.0082) H12A(-0.0827) H12B(0.0392) H17(-0.0652)
 H18A(0.2204) H18B(0.2242) H18C(0.2068) H19A(0.0188) H19B(0.0055) H19C(-0.0888)
 H21(-0.0924) H22(0.2426) H23(0.2315) H28A(-0.5024) H28B(-0.4139) H28C(-0.4469)
 H29A(-0.3603) H29B(-0.2678) H31A(-0.3022) H31B(-0.3772) H31C(-0.2428) H33(-
 0.3721) H34A(-0.5212) H34B(-0.5629) H34C(-0.604) H35A(-0.4354) H35B(-0.3439)
 H35C(-0.3133) H1(-0.1423) H2(-0.351) H7(-0.2842) H3'(0.4989) H5'(0.2811)
 H6'A(0.2264) H6'B(0.3591) H9'(0.0445) H11C(-0.0292) H11D(0.0993) H12C(0.111)
 H12D(-0.0064) H17'(0.0399) H18D(-0.2086) H18E(-0.202) H18F(-0.158)
 H19D(0.1141) H19E(0.1271) H19F(0.235) H21'(0.0344) H22'(-0.2781) H23'(-0.3109)
 H28D(0.5341) H28E(0.6041) H28F(0.5398) H29C(0.4046) H29D(0.4763) H31D(0.4435)
 H31E(0.3605) H31F(0.492) H33'(0.4792) H34D(0.4873) H34E(0.3479) H34F(0.4012)
 H35D(0.3479) H35E(0.3155) H35F(0.2466) H1'(0.27) H2'(0.3522) H7'(0.1973)
 Fixed Y: H3(0.0424) H5(0.0494) H6A(-0.0434) H6B(-0.0915) H9(0.0284)
 H11A(0.0637) H11B(0.0434) H12A(0.1551) H12B(0.1592) H17(0.2709) H18A(0.2092)
 H18B(0.195) H18C(0.133) H19A(-0.0815) H19B(-0.0722) H19C(-0.1164) H21(0.304)
 H22(0.3217) H23(0.3677) H28A(-0.0393) H28B(-0.0722) H28C(0.0071) H29A(-0.0736)
 H29B(-0.11) H31A(0.075) H31B(0.0086) H31C(0.0011) H33(0.233) H34A(0.2946)
 H34B(0.2642) H34C(0.2287) H35A(0.1937) H35B(0.1448) H35C(0.2237) H1(-0.0878)
 H2(0.0757) H7(0.1748) H3'(0.0925) H5'(0.0235) H6'A(-0.1017) H6'B(-0.1149)
 H9'(0.0094) H11C(-0.0038) H11D(-0.0115) H12C(0.1048) H12D(0.0762) H17'(0.2229)
 H18D(0.1407) H18E(0.0996) H18F(0.0646) H19D(-0.0879) H19E(-0.108) H19F(-
 0.1193) H21'(0.1969) H22'(0.2152) H23'(0.2193) H28D(0.0039) H28E(-0.0013)
 H28F(-0.0672) H29C(-0.0797) H29D(-0.0154) H31D(-0.1638) H31E(-0.0988) H31F(-
 0.0891) H33'(0.2394) H34D(0.1451) H34E(0.1352) H34F(0.1989) H35D(0.2839)
 H35E(0.2944) H35F(0.2388) H1'(-0.0355) H2'(0.0909) H7'(0.2191) 
 Fixed Z: H3(0.8787) H5(0.7349) H6A(0.6604) H6B(0.6875) H9(0.8907)
 H11A(0.7671) H11B(0.713) H12A(0.7334) H12B(0.6846) H17(0.8051) H18A(0.8807)
 H18B(0.7748) H18C(0.8429) H19A(0.8764) H19B(0.7692) H19C(0.8196) H21(0.6399)
 H22(0.7454) H23(0.5887) H28A(0.7624) H28B(0.6947) H28C(0.687) H29A(0.9116)
 H29B(0.8475) H31A(0.4319) H31B(0.4537) H31C(0.4296) H33(0.7688) H34A(0.6911)
 H34B(0.784) H34C(0.6903) H35A(0.5944) H35B(0.6488) H35C(0.6358) H1(0.9991)
 H2(1.0259) H7(0.9516) H3'(1.1227) H5'(1.2456) H6'A(1.2616) H6'B(1.2362)
 H9'(1.0797) H11C(1.2103) H11D(1.2586) H12C(1.2841) H12D(1.3246) H17'(1.2686)
 H18D(1.1528) H18E(1.2461) H18F(1.1567) H19D(1.0432) H19E(1.1478) H19F(1.0851)
 H21'(1.4427) H22'(1.3124) H23'(1.4732) H28D(1.2821) H28E(1.192) H28F(1.2295)
 H29C(1.0718) H29D(1.0334) H31D(1.5232) H31E(1.533) H31F(1.5029) H33'(1.3372)
 H34D(1.4137) H34E(1.4009) H34F(1.4569) H35D(1.239) H35E(1.3416) H35F(1.2797)
 H1'(0.9347) H2'(0.9394) H7'(1.0829) 
;
_olex2_submission_special_instructions 'No special instructions were received'