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_7228094
_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         'C19 H24 N2 O2'
_chemical_formula_sum            'C19 H24 N2 O2'
_chemical_formula_weight         312.40
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2017-01-21 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            4
_cell_length_a                   7.00418(8)
_cell_length_b                   15.07922(14)
_cell_length_c                   15.68796(17)
_cell_measurement_reflns_used    11390
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.5140
_cell_measurement_theta_min      4.0510
_cell_volume                     1656.92(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -129.00  47.00   1.00    1.00    --  -40.98   0.00-180.00  176
  2  \w     23.00  97.00   1.00    1.00    --   40.98-125.00-180.00   74
  3  \w     78.00 178.00   1.00    1.00    --  106.95  61.00-150.00  100
  4  \w     96.00 178.00   1.00    1.00    --  106.95 122.00 170.00   82
  5  \w     81.00 178.00   1.00    1.00    --  106.95  45.00 -30.00   97
  6  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00 120.00   85
  7  \w     94.00 178.00   1.00    1.00    --  106.95 125.00  90.00   84
  8  \w     74.00 178.00   1.00    1.00    --  106.95  77.00 150.00  104
  9  \w   -115.00 -17.00   1.00    1.00    --  -40.98 -37.00  60.00   98
 10  \w      8.00 117.00   1.00    1.00    --   40.98  77.00   0.00  109
 11  \w     74.00 178.00   1.00    1.00    --  106.95  77.00  30.00  104
 12  \w     78.00 178.00   1.00    1.00    --  106.95  61.00 -90.00  100
 13  \w     24.00 109.00   1.00    1.00    --  106.95 -94.00-150.00   85
 14  \w     78.00 178.00   1.00    1.00    --  106.95  61.00  90.00  100
 15  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00-180.00  109
 16  \w      1.00  82.00   1.00    1.00    --   40.98 -99.00 -60.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0832654000
_diffrn_orient_matrix_UB_12      -0.0644255000
_diffrn_orient_matrix_UB_13      0.0666104000
_diffrn_orient_matrix_UB_21      -0.0912750000
_diffrn_orient_matrix_UB_22      0.0786755000
_diffrn_orient_matrix_UB_23      0.0475499000
_diffrn_orient_matrix_UB_31      -0.1819178000
_diffrn_orient_matrix_UB_32      -0.0099982000
_diffrn_orient_matrix_UB_33      -0.0542821000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15731
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.682
_diffrn_reflns_theta_min         4.066
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1343 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3321
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0302
_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^)+(0.0440P)^2^+0.2910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0760
_refine_ls_wR_factor_ref         0.0769
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                3249
_reflns_number_total             3321
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra03411c2.cif
_cod_data_source_block           e0_6
_cod_original_cell_volume        1656.93(3)
_cod_database_code               7228094
_shelx_shelxl_version_number     2016/4
_reflns_odcompleteness_completeness 99.89
_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, All N(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)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C15(H15A,H15B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C7(H7), C9(H9), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.453
_oxdiff_exptl_absorpt_empirical_full_min 0.607