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_1545202
_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         'C18 H20 O8'
_chemical_formula_sum            'C18 H20 O8'
_chemical_formula_weight         364.34
_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   mixed
_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                 109.8246(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.46453(7)
_cell_length_b                   14.64416(12)
_cell_length_c                   8.31421(9)
_cell_measurement_reflns_used    10695
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.2990
_cell_measurement_theta_min      5.6390
_cell_volume                     854.979(15)
_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_environment      N~2~
_diffrn_ambient_temperature      120.01(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 -118.00  -86.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000   30.0000 32

  2 omega  -78.00  -12.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000  -60.0000 66

  3 omega  -70.00   27.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676   57.0000  -90.0000 97

  4 omega -117.00  -12.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000  150.0000 105

  5 omega  -76.00  -10.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000   30.0000 66

  6 omega  -57.00  -12.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000 -150.0000 45

  7 omega -114.00  -86.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -77.0000 -150.0000 28

  8 omega  -38.00  -13.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.3676  -57.0000   30.0000 25

  9 omega   18.00   54.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   37.0000  -90.0000 36

 10 omega    5.00   77.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000    0.0000 72

 11 omega   12.00   48.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676 -110.0000   79.0000 36

 12 omega   60.00  116.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   37.0000  -90.0000 56

 13 omega    4.00   65.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676  -99.0000  150.0000 61

 14 omega   18.00   62.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   57.0000   60.0000 44

 15 omega   15.00   47.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   57.0000  -60.0000 32

 16 omega   76.00  112.00   1.0000    4.5000
omega____ theta____ kappa____ phi______ frames
    -       41.3676   57.0000  -60.0000 36

 17 omega   56.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 57

 18 omega   80.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000    0.0000 97

 19 omega   59.00  116.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 57

 20 omega   80.00  107.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 27

 21 omega   83.00  129.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -150.0000 46

 22 omega   37.00  145.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -30.0000 108

 23 omega  119.00  173.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -90.0000 54

 24 omega   83.00  114.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 31

 25 omega  120.00  146.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -60.0000 26

 26 omega   84.00  114.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000    0.0000 30

 27 omega   84.00  163.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  120.0000 79

 28 omega   84.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   30.0000 25

 29 omega   83.00  112.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   60.0000 29

 30 omega   84.00  109.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -90.0000 25

 31 omega   84.00  129.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  -30.0000 45

 32 omega   81.00  107.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 26

 33 omega  117.00  175.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 58

 34 omega   39.00   95.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  120.0000 56

 35 omega   65.00   94.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000 -150.0000 29

 36 omega   80.00  159.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -150.0000 79

 37 omega   80.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  150.0000 25

 38 omega   79.00  152.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  -30.0000 73

 39 omega  139.00  176.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 37

 40 omega  116.00  176.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   30.0000 60

 41 omega   79.00  117.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 38

 42 omega  124.00  178.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   60.0000 54

 43 omega   79.00  138.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000   90.0000 59

 44 omega   83.00  110.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -120.0000 27

 45 omega   80.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 33

 46 omega   83.00  121.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000  150.0000 38

 47 omega  152.00  177.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 25

 48 omega   84.00  115.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 31

 49 omega   79.00  105.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000  120.0000 26

 50 omega   79.00  171.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -120.0000 92

 51 omega   87.00  112.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 25

 52 omega   83.00  113.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000 -180.0000 30
;
_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      -0.1447429000
_diffrn_orient_matrix_UB_12      0.0611272000
_diffrn_orient_matrix_UB_13      -0.1321637000
_diffrn_orient_matrix_UB_21      -0.1325277000
_diffrn_orient_matrix_UB_22      -0.0828622000
_diffrn_orient_matrix_UB_23      -0.0635778000
_diffrn_orient_matrix_UB_31      -0.0981801000
_diffrn_orient_matrix_UB_32      0.0214399000
_diffrn_orient_matrix_UB_33      0.1314495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11445
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.749
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         5.657
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.951
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81707
_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    1.415
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.1305
_exptl_crystal_size_mid          0.1204
_exptl_crystal_size_min          0.0913
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1435 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3027
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0272
_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^)+(0.0512P)^2^+0.0897P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0701
_reflns_Friedel_coverage         0.918
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3015
_reflns_number_total             3027
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np6b00759_si_003.cif
_cod_data_source_block           Comp_17
_cod_original_cell_volume        854.978(15)
_cod_database_code               1545202
_chemical_oxdiff_formula         'C20 H20 N4 O2'
_reflns_odcompleteness_completeness 100.00
_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
2.a Ternary CH refined with riding coordinates:
 C10(H10), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5A), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C18(H18A,H18B,H18C)
;
_shelx_res_checksum              22370
_shelx_hkl_checksum              74261
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'