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_1553292
_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         'C24 H28 O7'
_chemical_formula_sum            'C24 H28 O7'
_chemical_formula_weight         428.46
_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   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                   5.20049(4)
_cell_length_b                   18.36541(10)
_cell_length_c                   22.63281(12)
_cell_measurement_reflns_used    33625
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.7400
_cell_measurement_theta_min      3.8990
_cell_volume                     2161.64(2)
_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      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -25.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  -90.0000 54

  2 omega  -49.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000   60.0000 82

  3 omega  -48.00   33.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  150.0000 81

  4 omega  -48.00   14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 62

  5 omega  -45.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000 -120.0000 34

  6 omega  -93.00  -67.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000 -120.0000 26

  7 omega   14.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   57.0000 -120.0000 35

  8 omega   70.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   57.0000 -120.0000 40

  9 omega   76.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   37.0000    0.0000 39

 10 omega   57.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   37.0000   60.0000 27

 11 omega   21.00   49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   37.0000   60.0000 28

 12 omega   14.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   57.0000   90.0000 39

 13 omega   19.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000   90.0000 81

 14 omega  107.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  121.2380 27

 15 omega  153.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 25

 16 omega  142.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 28

 17 omega  132.00  175.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 43

 18 omega  128.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 36

 19 omega  125.00  151.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   75.0000   -8.8283 26

 20 omega  136.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 29

 21 omega  133.00  176.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 43

 22 omega  145.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 32

 23 omega  136.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 29

 24 omega  126.00  177.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 51

 25 omega  133.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 45

 26 omega  129.00  166.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000 -156.2142 37

 27 omega  122.00  148.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 26

 28 omega  122.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 43

 29 omega  121.00  147.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 26

 30 omega  121.00  178.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   74.0000   24.1017 57

 31 omega  110.00  136.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 26

 32 omega   84.00  136.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 52

 33 omega   86.00  119.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  150.0000 33

 34 omega   79.00  104.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  121.2380 25

 35 omega   83.00  164.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 81

 36 omega   87.00  133.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -60.0000 46

 37 omega   87.00  126.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 39

 38 omega   87.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 33

 39 omega   84.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 25

 40 omega   83.00  118.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 35

 41 omega   83.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 27

 42 omega   84.00  109.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 25

 43 omega   87.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -90.0000 25

 44 omega   79.00  110.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 31

 45 omega   83.00  146.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 63

 46 omega   79.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 86

 47 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 26

 48 omega   83.00  165.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 82

 49 omega   79.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 27

 50 omega   79.00  173.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -60.0000 94

 51 omega   83.00  147.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   59.0000 -173.7349 64

 52 omega   83.00  121.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 38

 53 omega   80.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   74.0000  -65.2235 26

 54 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 26

 55 omega   84.00  120.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 36

 56 omega   79.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 48

 57 omega   83.00  123.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 40

 58 omega   82.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   64.0000 -156.2142 26

 59 omega   79.00  131.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 52

 60 omega   80.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   75.0000   -8.8283 26

 61 omega   79.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 26

 62 omega   79.00  127.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 48

 63 omega   83.00  112.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 29

 64 omega   79.00  129.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 50

 65 omega   80.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   74.0000   24.1017 26

 66 omega   43.00   90.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 47

 67 omega   78.00  117.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 39

 68 omega  109.00  142.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 33

 69 omega   86.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 30

 70 omega   86.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000    0.0000 27

 71 omega   83.00  117.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -90.0000 34

 72 omega   78.00  130.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000 -150.0000 52

 73 omega   72.00   98.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 26

 74 omega   69.00  105.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 36

 75 omega   45.00   71.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -180.0000 26

 76 omega   37.00   62.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 25

 77 omega   37.00  114.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 77

 78 omega   64.00  145.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   30.0000 81

 79 omega   54.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000   60.0000 37

 80 omega   39.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 27

 81 omega   40.00   66.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -90.0000 26

 82 omega   48.00   88.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 40

 83 omega   43.00   68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000   30.0000 25

 84 omega   46.00   72.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 26

 85 omega   38.00   91.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   30.0000 53

 86 omega   39.00  116.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   60.0000 77

 87 omega   41.00   89.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 48

 88 omega   18.00   47.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   37.0000    0.0000 29

 89 omega   12.00   56.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   77.0000  -90.0000 44

 90 omega   22.00   53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   37.0000 -150.0000 31

 91 omega    2.00   80.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013  -99.0000 -150.0000 78

 92 omega    8.00   34.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013   86.0000  165.1951 26

 93 omega  -97.00   -9.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000  -30.0000 88
;
_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      -0.0400372000
_diffrn_orient_matrix_UB_12      0.0711955000
_diffrn_orient_matrix_UB_13      0.0348180000
_diffrn_orient_matrix_UB_21      0.0387068000
_diffrn_orient_matrix_UB_22      -0.0416322000
_diffrn_orient_matrix_UB_23      0.0584195000
_diffrn_orient_matrix_UB_31      0.2909072000
_diffrn_orient_matrix_UB_32      0.0153440000
_diffrn_orient_matrix_UB_33      -0.0029703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            51876
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.885
_diffrn_reflns_theta_min         3.099
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.938
_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    1.317
_exptl_crystal_description       plate
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.3946
_exptl_crystal_size_mid          0.1975
_exptl_crystal_size_min          0.0213
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1859 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4571
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0381
_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^)+(0.0703P)^2^+0.4701P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1009
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                4489
_reflns_number_total             4571
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00178_si_003.cif
_cod_data_source_block           3
_cod_database_code               1553292
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.91
_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:
 C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4)
;
_olex2_submission_special_instructions 'No special instructions were received'