Absolute Configurations of Naturally Occurring [5]- and [3]-Ladderanoic Acids: Isolation, Chiroptical Spectroscopy, and Crystallography.
Raghavan, Vijay; Johnson, Jordan L.; Stec, Donald F.; Song, Bongkeun; Zajac, Grzegorz; Baranska, Malgorzata; Harris, Constance M.; Schley, Nathan D.; Polavarapu, Prasad L.; Harris, Thomas M.; Journal of natural products 81 (2018) 2654–2666; doi:10.1021/acs.jnatprod.8b00458

data_1553391
_publ_section_title
;
 Absolute Configurations of Naturally Occurring [5]- and [3]-Ladderanoic
 Acids: Isolation, Chiroptical Spectroscopy, and Crystallography.
;
_journal_issue                   12
_journal_name_full               'Journal of natural products'
_journal_page_first              2654
_journal_page_last               2666
_journal_paper_doi               10.1021/acs.jnatprod.8b00458
_journal_volume                  81
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H32 O2'
_chemical_formula_sum            'C20 H32 O2'
_chemical_formula_weight         304.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-06-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.385(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   36.457(2)
_cell_length_b                   4.8860(3)
_cell_length_c                   20.2686(9)
_cell_measurement_reflns_used    3388
_cell_measurement_temperature    100.0(3)
_cell_measurement_theta_max      65.8290
_cell_measurement_theta_min      4.4960
_cell_volume                     3481.0(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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_environment      N~2~
_diffrn_ambient_temperature      100.0(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.984
_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    -49.00 -21.00   1.00   20.00    --  -36.45 -77.00  90.00   28
  2  \w   -102.00 -69.00   1.00   20.00    --  -36.45 -77.00  90.00   33
  3  \w    -62.00  31.00   1.00   20.00    --  -36.45  77.00-150.00   93
  4  \w    -51.00 -16.00   1.00   20.00    --  -36.45  57.00 -31.00   35
  5  \w   -104.00 -10.00   1.00   20.00    --  -36.45 -77.00   0.00   94
  6  \w    -63.00  29.00   1.00   20.00    --  -36.45  77.00 120.00   92
  7  \w     10.00  37.00   1.00   20.00    --   36.45  77.00 -30.00   27
  8  \w     31.00 111.00   1.00   60.00    --  100.36   0.00 -30.00   80
  9  \w     85.00 154.00   1.00   60.00    --  100.36  45.00   0.00   69
 10  \w     32.00 128.00   1.00   60.00    --  100.36 -80.00 126.09   96
 11  \w     34.00 118.00   1.00   60.00    --  100.36 -45.00-150.00   84
 12  \w     37.00 114.00   1.00   60.00    --  100.36 -45.00   0.00   77
 13  \w     82.00 108.00   1.00   60.00    --  100.36  61.00  30.00   26
 14  \w     38.00 118.00   1.00   60.00    --  100.36 -45.00 120.00   80
 15  \w     33.00 100.00   1.00   60.00    --  100.36 -80.00   1.32   67
 16  \w     61.00 108.00   1.00   60.00    --  100.36 -80.00 -55.46   47
 17  \w     84.00 134.00   1.00   60.00    --  100.36  61.00 150.00   50
 18  \w    112.00 143.00   1.00   60.00    --  100.36   0.00 -30.00   31
 19  \w     62.00  98.00   1.00   60.00    --  100.36 -80.00  67.89   36
 20  \w     64.00 118.00   1.00   60.00    --  100.36 -79.00-145.31   54
 21  \w     73.00 125.00   1.00   60.00    --  100.36 -80.00 -90.44   52
 22  \w    -85.00 -15.00   1.00   20.00    --  -36.70 -77.00 150.00   70
 23  \w    -30.00  52.00   1.00   20.00    --   36.70 -44.00 -18.00   82
 24  \w   -104.00 -10.00   1.00   20.00    --  -36.70 -77.00 -90.00   94
 25  \w      1.00  76.00   1.00   20.00    --   36.70 -99.00 -30.00   75
 26  \w     57.00  95.00   1.00   60.00    --  100.36 178.00 -90.00   38
 27  \w     89.00 115.00   1.00   60.00    --  100.36-111.00 -30.00   26
 28  \w   -104.00 -10.00   1.00   20.00    --  -36.70 -77.00 120.00   94
 29  \w   -104.00 -20.00   1.00   20.00    --  -36.70 -57.00-120.00   84
 30  \w   -106.00 -18.00   1.00   20.00    --  -36.70 -38.00  90.00   88
 31  \w   -104.00 -10.00   1.00   20.00    --  -36.70 -77.00-150.00   94
 32  \w     10.00 104.00   1.00   20.00    --   36.70  77.00   0.00   94
 33  \w     18.00 106.00   1.00   20.00    --   36.70  38.00 150.00   88
 34  \w     79.00 118.00   1.00   60.00    --  100.36  30.00  90.00   39
 35  \w    111.00 142.00   1.00   60.00    --  100.36 111.00 150.00   31
 36  \w     90.00 109.00   1.00   60.00    --  100.36-111.00 150.00   19
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131556000
_diffrn_orient_matrix_UB_12      0.2921875000
_diffrn_orient_matrix_UB_13      -0.0110336000
_diffrn_orient_matrix_UB_21      0.0203570000
_diffrn_orient_matrix_UB_22      -0.1106190000
_diffrn_orient_matrix_UB_23      -0.0520737000
_diffrn_orient_matrix_UB_31      -0.0365037000
_diffrn_orient_matrix_UB_32      0.0435798000
_diffrn_orient_matrix_UB_33      -0.0581244000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17577
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.394
_diffrn_reflns_theta_min         3.803
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.162
_exptl_crystal_description       needle
_exptl_crystal_F_000             1344
_exptl_crystal_recrystallization_method
'By slow evaporation of a warm MeOH/DCM solution'
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     409
_refine_ls_number_reflns         6145
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0490P)^2^+0.6890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1324
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.939
_reflns_number_gt                4279
_reflns_number_total             6145
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00458_si_004.cif
_cod_data_source_block           3-ladderane_acid
_cod_database_code               1553391
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H32O2
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(H12A)=Sof(C13B)=Sof(H13A)=Sof(H13B)=Sof(H14C)=Sof(H14D)=1-FVAR(1)
 Sof(H12B)=Sof(H14A)=Sof(H14B)=Sof(C18)=Sof(H18A)=Sof(H18B)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C19(H19), C9B(H9B),
 C11B(H11B), C12B(H12B), C12B(H12A), C15B(H15B), C16B(H16B), C17B(H17B),
 C18B(H18C)
3.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,
 H6B), C7(H7A,H7B), C8(H8A,H8B), C10(H10C,H10D), C13(H13C,H13D), C14(H14E,H14F),
  C20(H20C,H20D), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,
 H5BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C10B(H10A,H10B),
 C13B(H13A,H13B), C14B(H14A,H14B), C14B(H14C,H14D), C18(H18A,H18B), C19B(H19A,
 H19B), C20B(H20A,H20B)
3.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1B(H1B)
;
_shelx_res_checksum              58595
_shelx_hkl_checksum              24638
_olex2_date_sample_data_collection 2017-06-05
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.742