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_1553393
_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         'C28 H36 O3'
_chemical_formula_sum            'C28 H36 O3'
_chemical_formula_weight         420.57
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-03
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.817(5)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   5.3774(3)
_cell_length_b                   14.7492(6)
_cell_length_c                   43.061(2)
_cell_measurement_reflns_used    8096
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.8240
_cell_measurement_theta_min      4.1050
_cell_volume                     3414.9(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43g (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43g (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      air
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9937
_diffrn_measured_fraction_theta_max 0.9357
_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   -104.00 -10.00   1.00   10.00    --  -36.45 -77.00 150.00   94
  2  \w   -106.00  33.00   1.00   10.00    --  -36.45   0.00  30.00  139
  3  \w     10.00 104.00   1.00   10.00    --   36.45  77.00 -30.00   94
  4  \w    -31.00  63.00   1.00   10.00    --   36.45 -77.00-120.00   94
  5  \w     39.00 130.00   1.00   50.00    --  108.65 -30.00  30.00   91
  6  \w     91.00 176.00   1.00   50.00    --  108.65  61.00 -60.00   85
  7  \w     42.00 127.00   1.00   50.00    --  108.65 -61.00 -30.00   85
  8  \w     70.00 178.00   1.00   50.00    --  108.65  15.00 -60.00  108
  9  \w     91.00 176.00   1.00   50.00    --  108.65  61.00 -30.00   85
 10  \w     91.00 177.00   1.00   50.00    --  108.65  45.00   0.00   86
 11  \w     41.00 137.00   1.00   50.00    --  108.65 -80.00 149.71   96
 12  \w     41.00 135.00   1.00   50.00    --  108.65 -77.00-120.00   94
 13  \w     41.00 137.00   1.00   50.00    --  108.65 -80.00-147.29   96
 14  \w    -55.00  33.00   1.00   10.00    --  -36.45  38.00 120.00   88
 15  \w   -104.00 -20.00   1.00   10.00    --  -36.45 -57.00-150.00   84
 16  \w   -104.00 -10.00   1.00   10.00    --  -36.45 -77.00  30.00   94
 17  \w    -31.00  63.00   1.00   10.00    --   36.45 -77.00 150.00   94
 18  \w     39.00 119.00   1.00   60.00    --  108.65   0.00-180.00   80
 19  \w    -91.00 -65.00   1.00   10.00    --  -36.70 -77.00 -30.00   26
 20  \w    -39.00 -14.00   1.00   10.00    --  -36.70 -77.00 -30.00   25
 21  \w     54.00  80.00   1.00   10.00    --   36.70-125.00  60.00   26
 22  \w     41.00 117.00   1.00   60.00    --  108.03 -45.00-150.00   76
 23  \w     80.00 106.00   1.00   60.00    --  108.03 -94.00   0.00   26
 24  \w    139.00 165.00   1.00   60.00    --  108.03 111.00   0.00   26
 25  \w     59.00  89.00   1.00   60.00    --  108.03 -94.00  90.00   30
 26  \w     65.00 113.00   1.00   60.00    --  108.03-111.00-180.00   48
 27  \w     80.00 107.00   1.00   60.00    --  108.03-111.00 -30.00   27
 28  \w     87.00 116.00   1.00   60.00    --  108.03 -15.00 120.00   29
 29  \w   -104.00 -10.00   1.00   10.00    --  -36.70 -77.00 -90.00   94
 30  \w   -104.00 -20.00   1.00   10.00    --  -36.70 -57.00  60.00   84
 31  \w     18.00 102.00   1.00   10.00    --   36.70  38.00-150.00   84
 32  \w     23.00  90.00   1.00   10.00    --   36.70-125.00-180.00   67
 33  \w    -31.00  53.00   1.00   10.00    --   36.70 -57.00   0.00   84
 34  \w     20.00 104.00   1.00   10.00    --   36.70  57.00 -90.00   84
 35  \w     23.00  90.00   1.00   10.00    --   36.70-125.00  30.00   67
;
_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      -0.1212026000
_diffrn_orient_matrix_UB_12      -0.0243058000
_diffrn_orient_matrix_UB_13      0.0310931000
_diffrn_orient_matrix_UB_21      -0.0195398000
_diffrn_orient_matrix_UB_22      -0.0998179000
_diffrn_orient_matrix_UB_23      -0.0102997000
_diffrn_orient_matrix_UB_31      0.2590241000
_diffrn_orient_matrix_UB_32      -0.0188213000
_diffrn_orient_matrix_UB_33      0.0143686000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0542
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_number            34221
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        66.581
_diffrn_reflns_theta_max         66.581
_diffrn_reflns_theta_min         3.167
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43g (Rigaku Oxford Diffraction, 2015)
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    1.227
_exptl_crystal_description       plate
_exptl_crystal_F_000             1554.000
_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.061
_exptl_crystal_size_min          0.009
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     838
_refine_ls_number_reflns         11658
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0767
_refine_ls_R_factor_gt           0.0646
_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^)+(0.0940P)^2^+1.2690P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.1800
_reflns_Friedel_coverage         0.858
_reflns_Friedel_fraction_full    0.929
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                9725
_reflns_number_total             11658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00458_si_002.cif
_cod_data_source_block           5-ladderane_ester
_cod_database_code               1553393
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C28H36O3
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C18(H18), C9C(H9C), C11C(H11C), C12C(H12C), C13C(H13C), C14C(H14C), C15C(H15C),
  C16C(H16C), C17C(H17C), C18C(H18C), C9B(H9B), C11B(H11B), C12B(H12B),
 C13B(H13B), C14B(H14B), C15B(H15B), C16B(H16B), C17B(H17B), C18B(H18B)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
 C8(H8A,H8B), C10(H10A,H10B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
 C2C(H2CA,H2CB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB), C6C(H6CA,H6CB),
  C7C(H7CA,H7CB), C8C(H8CA,H8CB), C10C(H10C,H10D), C19C(H19C,H19D), C20C(H20C,
 H20D), C21C(H21C,H21D), C2B(H2BA,H2BB), C3B(H3BA,H3BB), C4B(H4BA,H4BB),
 C5B(H5BA,H5BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB), C8B(H8BA,H8BB), C10B(H10E,
 H10F), C19B(H19E,H19F), C20B(H20E,H20F), C21B(H21E,H21F)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C24C(H24C), C25C(H25C),
 C26C(H26C), C27C(H27C), C28C(H28C), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C28B(H28B)
;
_shelx_hkl_checksum              67863
_olex2_date_sample_data_collection 2016-12-06
_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 2.769
_oxdiff_exptl_absorpt_empirical_full_min 0.704