Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys kirkii Leaves.
Nyandoro, Stephen S.; Munissi, Joan J. E.; Gruhonjic, Amra; Duffy, Sandra; Pan, Fangfang; Puttreddy, Rakesh; Holleran, John P.; Fitzpatrick, Paul A.; Pelletier, Jerry; Avery, Vicky M.; Rissanen, Kari; Erdélyi, Máté; Journal of natural products 80 (2017) 114–125; doi:10.1021/acs.jnatprod.6b00759

data_1544922
_publ_section_title
;
 Polyoxygenated Cyclohexenes and Other Constituents of Cleistochlamys
 kirkii Leaves.
;
_journal_issue                   1
_journal_name_full               'Journal of natural products'
_journal_page_first              114
_journal_page_last               125
_journal_paper_doi               10.1021/acs.jnatprod.6b00759
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H14 O6'
_chemical_formula_sum            'C16 H14 O6'
_chemical_formula_weight         302.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-08-04
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.398(14)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.1535(9)
_cell_length_b                   11.5439(10)
_cell_length_c                   9.2553(12)
_cell_measurement_reflns_used    4705
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      76.7160
_cell_measurement_theta_min      5.0510
_cell_volume                     716.37(16)
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -17.00   31.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000   30.0000 16

  2 omega  -45.00  -18.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -37.0000  150.0000 9

  3 omega   36.00   72.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513   57.0000    0.0000 12

  4 omega   85.00  160.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 25

  5 omega  136.00  163.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000    0.0000 9

  6 omega  134.00  161.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 9

  7 omega  106.00  133.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   60.0000 9

  8 omega   92.00  128.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 12

  9 omega   89.00  116.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 9

 10 omega   83.00  176.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 31

 11 omega  151.00  178.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 9

 12 omega  102.00  153.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000  120.0000 17

 13 omega  102.00  129.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 9

 14 omega   60.00  111.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   15.0000    0.0000 17

 15 omega   85.00  118.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000    0.0000 11

 16 omega   84.00  111.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 9

 17 omega   79.00  124.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 15

 18 omega  107.00  146.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 13

 19 omega  103.00  130.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000 -180.0000 9

 20 omega   46.00   94.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 16

 21 omega   62.00   89.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 9

 22 omega   71.00   98.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   60.0000 9

 23 omega   93.00  120.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 9

 24 omega   59.00  107.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 16

 25 omega   56.00   83.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 9

 26 omega   44.00   80.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   90.0000 12

 27 omega   43.00   73.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -30.0000 10

 28 omega   32.00   59.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -15.0000    0.0000 9

 29 omega   36.00   84.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000   60.0000 16

 30 omega   30.00   69.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  120.0000 13

 31 omega    4.00   46.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -99.0000  -60.0000 14

 32 omega   81.00  111.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 10

 33 omega   51.00  108.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -90.0000 19

 34 omega   56.00   83.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 9

 35 omega   45.00   72.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -120.0000 9

 36 omega   33.00   87.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -120.0000 18

 37 omega   32.00   77.00   3.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 15

 38 omega  -49.00   32.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000 -150.0000 27

 39 omega -115.00  -61.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -37.0000  150.0000 18

 40 omega -121.00   -1.00   3.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -19.0000   30.0000 40
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6223
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.734
_diffrn_reflns_theta_max         66.734
_diffrn_reflns_theta_min         5.098
_exptl_absorpt_coefficient_mu    0.913
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.81601
_exptl_absorpt_correction_type   gaussian
_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)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.401
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1145 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2499
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_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^)+(0.0306P)^2^+0.1004P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0590
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.978
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2475
_reflns_number_total             2499
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00759_si_004.cif
_cod_data_source_block           Comp_19
_cod_depositor_comments          'Adding full bibliography for 1544922.cif.'
_cod_database_code               1544922
_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
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_shelx_res_checksum              78471
_shelx_hkl_checksum              35698
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'