In Depth Analysis of Chiroptical Properties of Enones Derived from Abietic Acid.
Masnyk, Marek; Butkiewicz, Aleksandra; Górecki, Marcin; Luboradzki, Roman; Paluch, Piotr; Potrzebowski, Marek J.; Frelek, Jadwiga; The Journal of organic chemistry 83 (2018) 3547–3561; doi:10.1021/acs.joc.7b02911

data_4035489
_publ_section_title
;
 In Depth Analysis of Chiroptical Properties of Enones Derived from
 Abietic Acid.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3547
_journal_page_last               3561
_journal_paper_doi               10.1021/acs.joc.7b02911
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C21 H32 O4'
_chemical_formula_sum            'C21 H32 O4'
_chemical_formula_weight         348.46
_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'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-11
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled Nov  7 2012 10:32:32, GUI svn.r4372)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.22740(18)
_cell_length_b                   14.7184(5)
_cell_length_c                   20.1210(6)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.0427
_cell_measurement_theta_min      2.9999
_cell_volume                     1844.24(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean 16.2974
_diffrn_measured_fraction_theta_full 0.9990
_diffrn_measured_fraction_theta_max 0.9949
_diffrn_measurement_details
;
  1 omega   -4.00   23.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 27

  2 omega  -13.00   14.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 27

  3 omega   44.00   69.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 25

  4 omega  -47.00   29.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000    0.0000 76

  5 omega   -2.00   29.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   37.0000  120.0000 31

  6 omega  -35.00   11.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000 -120.0000 46

  7 omega   54.00   85.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -77.0000   30.0000 31

  8 omega   40.00   87.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -180.0000 47

  9 omega  137.00  169.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 32

 10 omega   98.00  146.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000  120.0000 48

 11 omega   78.00  177.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   25.0000   30.0000 99

 12 omega   72.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000   30.0000 30

 13 omega  101.00  143.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000   30.0000 42

 14 omega   75.00  102.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -30.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0868906000
_diffrn_orient_matrix_UB_12      0.0044064000
_diffrn_orient_matrix_UB_13      0.0715892000
_diffrn_orient_matrix_UB_21      -0.0225378000
_diffrn_orient_matrix_UB_22      0.1042251000
_diffrn_orient_matrix_UB_23      -0.0008834000
_diffrn_orient_matrix_UB_31      -0.2305932000
_diffrn_orient_matrix_UB_32      -0.0086942000
_diffrn_orient_matrix_UB_33      0.0270570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4398
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.190
_diffrn_reflns_theta_min         3.721
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.678
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91738
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.885
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0399
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^-1.0000sin\q] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0.426
_reflns_Friedel_fraction_full    0.612
_reflns_Friedel_fraction_max     0.576
_reflns_number_gt                2729
_reflns_number_total             2952
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02911_si_004.cif
_cod_data_source_block           ab79c_01
_cod_database_code               4035489
_chemical_oxdiff_formula         'C20 H20 O3'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H10A,H10B} of C10, {H13A,H13B} of C13, H15 of C15, {H9A,H9B} of C9, {H4A,
  H4B} of C4, H11 of C11, H7 of C7, {H14A,H14B} of C14, {H1A,H1B} of C1, H3 of
  C3
 At 1.5 times of:
  {H16A,H16B,H16C} of C16, {H19A,H19B,H19C} of C19, {H17A,H17B,H17C} of C17,
  {H21A,H21B,H21C} of C21, H2 of O2, {H18A,H18B,H18C} of C18
;
_shelx_hkl_checksum              81294
_shelx_res_checksum              76426
_shelxl_version_number           2013-4