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_4033540
_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 O5'
_chemical_formula_sum            'C21 H32 O5'
_chemical_formula_weight         364.46
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-08
_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                   6.3525(3)
_cell_length_b                   14.6783(10)
_cell_length_c                   20.3136(14)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      69.8495
_cell_measurement_theta_min      3.0081
_cell_volume                     1894.1(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -50.00   -2.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   25.0000  -60.0000 48

  2 omega   -1.00   39.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   25.0000  -60.0000 40

  3 omega  -75.00  -35.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 40

  4 omega  -98.00  -60.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 38

  5 omega    1.00   68.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000    0.0000 67

  6 omega  -17.00   76.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -37.0000   60.0000 93

  7 omega   97.00  123.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 26

  8 omega   34.00  124.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000 -150.0000 90

  9 omega  109.00  167.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   37.0000   90.0000 58

 10 omega   38.00   64.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   30.0000 26

 11 omega   35.00   90.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 55

 12 omega   38.00   90.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 52

 13 omega   51.00   88.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000   90.0000 37

 14 omega   87.00  112.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000    0.0000 25

 15 omega   43.00   88.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   60.0000 45

 16 omega   87.00  166.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  150.0000 79

 17 omega   50.00   92.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -37.0000 -120.0000 42

 18 omega   86.00  173.00   1.0000    4.8900
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 87
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0767976000
_diffrn_orient_matrix_UB_12      -0.0629057000
_diffrn_orient_matrix_UB_13      -0.0557486000
_diffrn_orient_matrix_UB_21      -0.1478832000
_diffrn_orient_matrix_UB_22      0.0488174000
_diffrn_orient_matrix_UB_23      -0.0486347000
_diffrn_orient_matrix_UB_31      0.1765679000
_diffrn_orient_matrix_UB_32      0.0681906000
_diffrn_orient_matrix_UB_33      -0.0167090000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7834
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.979
_diffrn_reflns_theta_min         3.715
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21b (release 03-02-2012 CrysAlis171 .NET)
(compiled Feb  3 2012,10:37:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1131 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_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^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1424
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                3073
_reflns_number_total             3535
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02911_si_003.cif
_cod_data_source_block           ab099a_01
_cod_depositor_comments
'Adding full bibliography for 4033540--4033541.cif.'
_cod_database_code               4033540
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  {H14A,H14B} of C14, H3A of C3, {H9A,H9B} of C9, {H1A,H1B} of C1, {H4A,H4B}
  of C4, {H10A,H10B} of C10, {H13A,H13B} of C13, H7 of C7, H11 of C11, H15 of
  C15
 At 1.5 times of:
  {H19A,H19B,H19C} of C19, {H21A,H21B,H21C} of C21, {H16A,H16B,H16C} of C16,
  {H17A,H17B,H17C} of C17, {H18A,H18B,H18C} of C18
2.a Ternary CH refined with riding coordinates:
 C11(H11), C15(H15), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C10(H10A,H10B), C13(H13A,H13B), C14(H14A,H14B), C9(H9A,H9B),
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C)
;
_shelx_hkl_checksum              89256
_shelx_res_checksum              18288
_shelxl_version_number           2013-4