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_1553392
_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 H30 O2'
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.44
_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             2017-04-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.556(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   64.164(2)
_cell_length_b                   4.8171(2)
_cell_length_c                   10.9786(4)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      70.8670
_cell_measurement_theta_min      4.1280
_cell_volume                     3393.2(2)
_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    'ShelXD (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.3012
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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    -53.00  31.00   0.75    6.21    --  -36.45  57.00  30.00  112
  2  \w   -104.00 -20.00   0.75    6.21    --  -36.45 -57.00  60.00  112
  3  \w     91.00 175.00   0.75   24.86    --  108.65  61.00  60.00  112
  4  \w   -104.00 -11.00   0.75    6.21    --  -36.45 -77.00 -30.00  124
  5  \w     41.00 137.00   0.75   24.86    --  108.65 -80.00 -13.44  128
  6  \w     20.00 104.00   0.75    6.21    --   36.45  57.00 -30.00  112
  7  \w    -31.00  53.00   0.75    6.21    --   36.45 -57.00 -90.00  112
  8  \w      7.00 107.50   0.75    6.21    --   36.45  19.00  30.00  134
  9  \w      7.00 107.50   0.75    6.21    --   36.45  19.00-120.00  134
 10  \w     18.00 105.00   0.75    6.21    --   36.45  38.00 150.00  116
 11  \w    -31.00  53.00   0.75    6.21    --   36.45 -57.00 -60.00  112
 12  \w     10.00 103.00   0.75    6.21    --   36.45  77.00-120.00  124
 13  \w     82.00 175.00   0.75   24.86    --  108.65  77.00 -30.00  124
 14  \w     87.00 177.00   0.75   24.86    --  108.65  30.00   0.00  120
 15  \w     82.00 175.00   0.75   24.86    --  108.65  77.00  30.00  124
 16  \w     39.00 129.00   0.75   24.86    --  108.65 -30.00  60.00  120
 17  \w     87.00 158.25   0.75   24.86    --  108.65  30.00  60.00   95
 18  \w     82.00 107.50   0.75   24.86    --  108.65  77.00 -60.00   34
 19  \w     92.00 118.25   0.75   24.86    --  108.65  61.00 -60.00   35
 20  \w     92.00 118.25   0.75   24.86    --  108.65  45.00 -90.00   35
 21  \w    131.00 157.25   0.75   24.86    --  108.65  77.00 -90.00   35
 22  \w     44.00 132.50   0.75   24.86    --  108.65 -77.00 150.00  118
 23  \w    126.00 171.00   0.75   24.86    --  108.65  77.00   0.00   60
 24  \w     82.00 108.25   0.75   24.86    --  108.65  77.00   0.00   35
 25  \w     87.00 113.25   0.75   24.86    --  108.65  30.00 -30.00   35
 26  \w     91.00 120.25   0.75   24.86    --  108.65  61.00  30.00   39
 27  \w     91.00 117.25   0.75   24.86    --  108.65  61.00   0.00   35
 28  \w     82.00 108.25   0.75   24.86    --  108.65  77.00 -90.00   35
 29  \w     91.00 117.25   0.75   24.86    --  108.65  61.00 -30.00   35
 30  \w     95.00 127.25   0.75   24.86    --  108.65  30.00 -60.00   43
 31  \w     91.00 128.50   0.75   24.86    --  108.65  45.00  60.00   50
 32  \w     94.00 120.25   0.75   24.86    --  108.65  45.00   0.00   35
 33  \w     91.00 116.50   0.75   24.86    --  108.65  45.00  30.00   34
 34  \w     72.00  98.25   0.75   24.86    --  108.65  15.00  30.00   35
 35  \w     97.00 129.25   0.75   24.86    --  108.65 -80.00  19.02   43
 36  \w     97.00 123.25   0.75   24.86    --  108.65  61.00 -90.00   35
 37  \w     94.00 120.25   0.75   24.86    --  108.65  45.00 -60.00   35
 38  \w     87.00 113.25   0.75   24.86    --  108.65  30.00  30.00   35
 39  \w     89.00 115.25   0.75   24.86    --  108.65  15.00   0.00   35
 40  \w     44.00  47.00   0.75   24.86    --  108.65 -61.00 -90.00    4
;
_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      -0.0146452000
_diffrn_orient_matrix_UB_12      0.1077670000
_diffrn_orient_matrix_UB_13      -0.1016723000
_diffrn_orient_matrix_UB_21      -0.0184531000
_diffrn_orient_matrix_UB_22      -0.0094509000
_diffrn_orient_matrix_UB_23      0.0885371000
_diffrn_orient_matrix_UB_31      0.0046351000
_diffrn_orient_matrix_UB_32      0.3009056000
_diffrn_orient_matrix_UB_33      0.0391372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       76
_diffrn_reflns_limit_h_min       -76
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            16132
_diffrn_reflns_point_group_measured_fraction_full 0.920
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         4.027
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.572
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (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    1.184
_exptl_crystal_description       plate
_exptl_crystal_F_000             1328
_exptl_crystal_recrystallization_method
'By slow evaporation of a saturated methanol solution.'
_exptl_crystal_size_max          0.259
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 1539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5530
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0484
_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^)+(0.0800P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1383
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.826
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                4643
_reflns_number_total             5530
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np8b00458_si_003.cif
_cod_data_source_block           5-ladderane_acid
_cod_database_code               1553392
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C20H30O2
_reflns_odcompleteness_completeness 99.26
_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
 At 1.5 times of:
  All O(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), 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), C2B(H2BB,H2BC),
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C6B(H6BA,H6BB), C7B(H7BA,H7BB),
  C8B(H8BA,H8BB), C10B(H10C,H10D), C19B(H19C,H19D), C20B(H20C,H20D)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2B(H2BA)
;
_shelx_res_checksum              30486
_shelx_hkl_checksum              24767
_olex2_date_sample_data_collection 2017-04-10
_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 3.129
_oxdiff_exptl_absorpt_empirical_full_min 0.594