Ervadivamines A and B, Two Unusual Trimeric Monoterpenoid Indole Alkaloids from Ervatamia divaricata.
Liu, Zhi-Wen; Zhang, Jian; Li, Song-Tao; Liu, Ming-Qun; Huang, Xiao-Jun; Ao, Yun-Lin; Fan, Chun-Lin; Zhang, Dong-Mei; Zhang, Qing-Wen; Ye, Wen-Cai; Zhang, Xiao-Qi; The Journal of organic chemistry 83 (2018) 10613–10618; doi:10.1021/acs.joc.8b01371

data_4035116
_publ_section_title
;
 Ervadivamines A and B, Two Unusual Trimeric Monoterpenoid Indole
 Alkaloids from Ervatamia divaricata.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10613
_journal_page_last               10618
_journal_paper_doi               10.1021/acs.joc.8b01371
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C62 H78 N6 O5'
_chemical_formula_sum            'C62 H78 N6 O5'
_chemical_formula_weight         987.30
_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
_audit_creation_date             2018-03-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6557(2)
_cell_length_b                   17.4453(3)
_cell_length_c                   29.2029(5)
_cell_measurement_reflns_used    27848
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4600
_cell_measurement_theta_min      4.6020
_cell_volume                     6447.49(19)
_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      100.00(10)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            60833
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.768
_diffrn_reflns_theta_min         3.807
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68705
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless?
_exptl_crystal_density_diffrn    1.017
_exptl_crystal_description       block
_exptl_crystal_F_000             2128
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 4787 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.95(9)
_refine_ls_extinction_coef       0.00024(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         12883
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0423
_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^)+(0.0579P)^2^+0.7029P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1084
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                11907
_reflns_number_total             12883
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01371_si_003.cif
_cod_data_source_block           e_l_2_sq
_cod_original_cell_volume        6447.47(18)
_cod_database_code               4035116
_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. Rigid bond restraints
 C3, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C3 \\sim C14: within 1.7A with sigma of 0.01 and sigma for terminal atoms of
0.08
4.a Ternary CH refined with riding coordinates:
 C3*(H3*), C21(H21), C3'(H3'), C5'(H5'), C5*(H5*), C16'(H16'), C16*(H16*), C15*
 (H15*), C15'(H15'), C16(H16), C20*(H20*), C20(H20), C20'(H20'), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C6'(H6'A,H6'B), C21*(H21A,H21B), C6*(H6*A,H6*B), C14*(H14A,H14B), C14'(H14C,
 H14D), C21'(H21C,H21D), C19*(H19A,H19B), C19'(H19C,H19D), C19(H19E,H19F),
 C6(H6A,H6B), C5(H5A,H5B), C15(H15A,H15B), C17(H17A,H17B), C3(H3A,H3B)
4.c Aromatic/amide H refined with riding coordinates:
 N1*(H1*), N1'(H1'), C12(H12), C9*(H9*), C12*(H12*), C9(H9), C10*(H10*),
 C12'(H12'), C9'(H9'), C11*(H11*), C11'(H11'), C10'(H10')
4.d Idealised Me refined as rotating group:
 C23*(H23A,H23B,H23C), C24*(H24A,H24B,H24C), C24'(H24D,H24E,H24F), C18(H18A,
 H18B,H18C), C23'(H23D,H23E,H23F), C18*(H18D,H18E,H18F), C22(H22A,H22B,H22C),
 C18'(H18G,H18H,H18I)
;
_platon_squeeze_void_probe_radius 1.20
_shelx_res_checksum              93800
_shelx_hkl_checksum              14259
_shelx_fab_checksum              40364
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'