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_1544956
_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         'C35 H44 O11'
_chemical_formula_sum            'C35 H44 O11'
_chemical_formula_weight         640.70
_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             2016-05-25
_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                   9.22870(10)
_cell_length_b                   12.5822(2)
_cell_length_c                   28.2476(3)
_cell_measurement_reflns_used    22941
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      66.8760
_cell_measurement_theta_min      3.7940
_cell_volume                     3280.04(7)
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details
;
  1 omega   -2.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938 -126.0000  -90.0000 99

  2 omega   11.00  115.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.7938   57.0000 -150.0000 104

  3 omega   19.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   60.0000 58

  4 omega   16.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -180.0000 53

  5 omega   16.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 53

  6 omega   19.00  124.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   60.0000 105

  7 omega   15.00  127.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000 -120.0000 112

  8 omega   22.00  119.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -164.0000 -103.0000 97

  9 omega   16.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 53

 10 omega   68.00  126.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000  -90.0000 58

 11 omega   53.00   78.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -126.0000   60.0000 25

 12 omega   53.00   93.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   60.0000 40

 13 omega   81.00  158.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  126.0000  150.0000 77

 14 omega   56.00   81.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000   60.0000 25

 15 omega   20.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 57

 16 omega   68.00  102.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 34

 17 omega  131.00  168.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -120.0000 37

 18 omega   16.00   41.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -150.0000 25

 19 omega   10.00  132.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000   75.3608 122

 20 omega   17.00   97.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000  135.5394 80

 21 omega   55.00   98.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000   48.2680 43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1660174000
_diffrn_orient_matrix_UB_12      0.0033034000
_diffrn_orient_matrix_UB_13      -0.0057371000
_diffrn_orient_matrix_UB_21      -0.0018375000
_diffrn_orient_matrix_UB_22      0.1210988000
_diffrn_orient_matrix_UB_23      0.0079880000
_diffrn_orient_matrix_UB_31      0.0180666000
_diffrn_orient_matrix_UB_32      -0.0177717000
_diffrn_orient_matrix_UB_33      0.0536183000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            29401
_diffrn_reflns_theta_full        67.11
_diffrn_reflns_theta_max         67.11
_diffrn_reflns_theta_min         3.85
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77528
_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    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.00141(13)
_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   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0284
_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^)+(0.0383P)^2^+0.6549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0724
_reflns_number_gt                5731
_reflns_number_total             5817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b03479_si_005.cif
_cod_data_source_block           exp_moluccensinA
_cod_database_code               1544956
_reflns_odcompleteness_completeness 97.40
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C5(H5), C9(H9), C17(H17), C33(H33), C37(H37)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C29(H29A,H29B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C28(H28A,H28B,H28C), C31(H31A,H31B,
 H31C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C38(H38A,H38B,H38C), C39(H39A,
 H39B,H39C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'