Ervaoffines E–G, three iboga-type alkaloids featuring ring C cleavage and rearrangement from Ervatamia officinalis
Liu, Zhi-Wen; Tang, Ben-Qin; Zhang, Qing-Hua; Wang, Wen-Jing; Huang, Xiao-Jun; Zhang, Jian; Shi, Lei; Zhang, Xiao-Qi; Ye, Wen-Cai; RSC Adv. 7 (2017) 21883–; doi:10.1039/C7RA03411C

data_7228095
_publ_section_title
;
 Ervaoffines E--G, three iboga-type alkaloids featuring ring C cleavage
 and rearrangement from Ervatamia officinalis
;
_journal_issue                   35
_journal_name_full               'RSC Adv.'
_journal_page_first              21883
_journal_paper_doi               10.1039/C7RA03411C
_journal_volume                  7
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H24 N2 O2'
_chemical_formula_sum            'C20 H24 N2 O2'
_chemical_formula_weight         324.41
_chemical_name_systematic        'Lirofolines A'
_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   geom
_audit_creation_date             2016-12-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-26 deposited with the CCDC.
2017-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.75070(10)
_cell_length_b                   14.3787(2)
_cell_length_c                   27.3576(4)
_cell_measurement_reflns_used    12788
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      62.8500
_cell_measurement_theta_min      3.4720
_cell_volume                     3442.23(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.9408
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details
;
  1 omega  -88.00  -58.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000    0.0000 30

  2 omega -106.00  -72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  -90.0000 34

  3 omega  -99.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184  -57.0000   60.0000 26

  4 omega  -11.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   19.0000 -120.0000 107

  5 omega   35.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184 -178.0000  -30.0000 28

  6 omega   20.00   51.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 31

  7 omega   42.00  122.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -180.0000 80

  8 omega   70.00  102.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 32

  9 omega   39.00   68.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000  150.0000 29

 10 omega   94.00  141.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000    0.0000 47

 11 omega   25.00   67.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  120.0000 42

 12 omega  127.00  154.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000 -180.0000 27

 13 omega   60.00   86.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000 -150.0000 26

 14 omega   24.00   76.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -60.0000 52

 15 omega   18.00   57.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -180.0000 39

 16 omega   74.00  109.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 35

 17 omega   31.00  114.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000  -60.0000 83

 18 omega  116.00  144.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 28

 19 omega  120.00  158.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -60.0000 38

 20 omega   46.00   80.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -180.0000 34

 21 omega   64.00  108.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000  -30.0000 44

 22 omega   27.00   53.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000  -90.0000 26

 23 omega  110.00  136.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -30.0000 26

 24 omega   52.00   82.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000 -150.0000 30

 25 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000  150.0000 52

 26 omega -109.00  -57.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.1184 -178.0000   30.0000 52

 27 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000  -60.0000 89

 28 omega   13.00  102.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   57.0000    0.0000 89

 29 omega    3.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       33.1184   77.0000   60.0000 100

 30 omega   69.00  159.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   60.0000 90

 31 omega   19.00   77.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000   30.0000 58

 32 omega   18.00   90.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -111.0000  150.0000 72

 33 omega   60.00  161.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   77.0000 -180.0000 101

 34 omega   69.00  161.00   1.0000    4.7000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   51.0000 -110.0000 92
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1093229000
_diffrn_orient_matrix_UB_12      0.0749686000
_diffrn_orient_matrix_UB_13      -0.0199110000
_diffrn_orient_matrix_UB_21      0.0072406000
_diffrn_orient_matrix_UB_22      -0.0451158000
_diffrn_orient_matrix_UB_23      -0.0510262000
_diffrn_orient_matrix_UB_31      -0.1377959000
_diffrn_orient_matrix_UB_32      -0.0618128000
_diffrn_orient_matrix_UB_33      0.0131126000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        62.681
_diffrn_reflns_theta_max         62.681
_diffrn_reflns_theta_min         3.472
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.252
_exptl_crystal_F_000             1392
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         5506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0291
_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^)+(0.0394P)^2^+0.3711P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0737
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5279
_reflns_number_total             5506
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra03411c2.cif
_cod_data_source_block           tangbenqin_oa-6b
_cod_database_code               7228095
_chemical_oxdiff_formula         CHNO
_reflns_odcompleteness_completeness 94.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C14(H14), C16(H16), C20(H20), C21(H21), C14'(H14'), C16'(H16'), C20'(H20'),
 C21'(H21')
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B),
 C3'(H3'A,H3'B), C5'(H5'A,H5'B), C15'(H15C,H15D), C17'(H17C,H17D), C19'(H19C,
 H19D)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C11(H11), C12(H12), C6'(H6'), C9'(H9'), C11'(H11'), C12'(H12')
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C18'(H18D,H18E,H18F), C22'(H22D,
 H22E,H22F)
;
_shelx_shelxl_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'