Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas bussei.
Abdissa, Negera; Pan, Fangfang; Gruhonjic, Amra; Gräfenstein, Jürgen; Fitzpatrick, Paul A.; Landberg, Göran; Rissanen, Kari; Yenesew, Abiy; Erdélyi, Máté; Journal of natural products 79 (2016) 2181–2187; doi:10.1021/acs.jnatprod.6b00178

data_1553291
_publ_section_title
;
 Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas
 bussei.
;
_journal_issue                   9
_journal_name_full               'Journal of natural products'
_journal_page_first              2181
_journal_page_last               2187
_journal_paper_doi               10.1021/acs.jnatprod.6b00178
_journal_volume                  79
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H26 O7'
_chemical_formula_sum            'C23 H26 O7'
_chemical_formula_weight         414.44
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-25
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1399(2)
_cell_length_b                   11.2214(3)
_cell_length_c                   19.3280(5)
_cell_measurement_reflns_used    9277
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.3650
_cell_measurement_theta_min      4.5250
_cell_volume                     1982.33(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 20.7907
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega   83.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 27

  2 omega   83.00  154.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 71

  3 omega  125.00  152.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 27

  4 omega  125.00  151.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

  5 omega   85.00  112.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   63.0000   35.9788 27

  6 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 26

  7 omega   83.00  114.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 31

  8 omega   83.00  141.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 58

  9 omega   83.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 95

 10 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 26

 11 omega   79.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 98

 12 omega  112.00  175.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  -90.0000 63

 13 omega  118.00  147.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 29

 14 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 26

 15 omega   83.00  140.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 57

 16 omega   83.00  110.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 27

 17 omega   83.00  123.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 40

 18 omega   82.00  128.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   65.0000  -54.3145 46

 19 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 26

 20 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 26

 21 omega   79.00  176.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 97

 22 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   37.0000 -120.0000 26

 23 omega   79.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 27

 24 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 26

 25 omega   79.00  177.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 98

 26 omega   79.00  106.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 27

 27 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 26

 28 omega   80.00  153.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   75.0000   -3.9232 73

 29 omega   83.00  109.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 26

 30 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 26

 31 omega   79.00  105.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

 32 omega   79.00  178.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 99

 33 omega   76.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   77.0000  120.0000 26

 34 omega   70.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   37.0000   90.0000 42

 35 omega   69.00  111.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   57.0000   30.0000 42

 36 omega   21.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   37.0000   90.0000 44

 37 omega   14.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   57.0000   30.0000 46

 38 omega    9.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   77.0000  120.0000 63

 39 omega    9.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   77.0000  -90.0000 82

 40 omega   19.00   48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   37.0000 -120.0000 29

 41 omega    9.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   77.0000 -180.0000 80

 42 omega   30.00   92.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 62

 43 omega   36.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 80

 44 omega   47.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513 -125.0000 -180.0000 44

 45 omega   29.00  101.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 72

 46 omega   50.00  116.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 66

 47 omega   48.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513 -125.0000   90.0000 32

 48 omega   30.00   77.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000    0.0000 47

 49 omega   29.00  103.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   90.0000 74

 50 omega  -49.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000 -120.0000 72

 51 omega  -51.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -57.0000    0.0000 37

 52 omega  -54.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -77.0000  -30.0000 43

 53 omega  -93.00  -59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -77.0000  -30.0000 34

 54 omega  -46.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000   60.0000 79

 55 omega  -49.00   32.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000  150.0000 81

 56 omega  -66.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   77.0000  -60.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0263555000
_diffrn_orient_matrix_UB_12      0.0179354000
_diffrn_orient_matrix_UB_13      0.0780407000
_diffrn_orient_matrix_UB_21      0.1610090000
_diffrn_orient_matrix_UB_22      -0.0319499000
_diffrn_orient_matrix_UB_23      0.0146415000
_diffrn_orient_matrix_UB_31      0.0425438000
_diffrn_orient_matrix_UB_32      0.1322426000
_diffrn_orient_matrix_UB_33      -0.0070860000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            33097
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.446
_diffrn_reflns_theta_min         4.556
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           n/a
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.940
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.389
_exptl_crystal_description       plate
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.4183
_exptl_crystal_size_mid          0.291
_exptl_crystal_size_min          0.0361
_refine_diff_density_max         0.618
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Flack x determined using 1596 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0494
_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^)+(0.0918P)^2^+0.8491P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1420
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                3865
_reflns_number_total             4156
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00178_si_004.cif
_cod_data_source_block           4
_cod_original_cell_volume        1982.32(9)
_cod_database_code               1553291
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C30 H60 O5'
_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:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C14(H14), C13(H13), C17(H17), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C22(H22A,H22B,H22C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'