Ervatamines A-I, Anti-inflammatory Monoterpenoid Indole Alkaloids with Diverse Skeletons from Ervatamia hainanensis.
Zhang, Dong-Bo; Yu, Dao-Geng; Sun, Meng; Zhu, Xu-Xin; Yao, Xiao-Jun; Zhou, Shuang-Yan; Chen, Jian-Jun; Gao, Kun; Journal of natural products 78 (2015) 1253–1261; doi:10.1021/acs.jnatprod.5b00051

data_1520112
_publ_section_title
;
 Ervatamines A-I, Anti-inflammatory Monoterpenoid Indole Alkaloids with
 Diverse Skeletons from Ervatamia hainanensis.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1253
_journal_page_last               1261
_journal_paper_doi               10.1021/acs.jnatprod.5b00051
_journal_volume                  78
_journal_year                    2015
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C20 H24 N2 O2, C2 H6 O, H2 O'
_chemical_formula_sum            'C22 H32 N2 O4'
_chemical_formula_weight         388.49
_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   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-05-12
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.33312(18)
_cell_length_b                   12.6666(3)
_cell_length_c                   25.6966(10)
_cell_measurement_reflns_used    4378
_cell_measurement_temperature    173
_cell_measurement_theta_max      69.3200
_cell_measurement_theta_min      4.8540
_cell_volume                     2061.36(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
  1 omega  -70.00  -13.60   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  147.0000   -6.0000 47

  2 omega  -21.00   69.00   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 75

  3 omega   33.00  124.20   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   50.0000  125.0000 76

  4 omega   33.00  123.00   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   90.0000 75

  5 omega   33.00  123.00   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 75

  6 omega   33.00  123.00   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -120.0000 75

  7 omega   37.00  178.60   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000   90.0000 118

  8 omega   36.00   94.80   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 49

  9 omega   35.00   95.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 50

 10 omega   36.00   94.80   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 49

 11 omega   36.00   94.80   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 49

 12 omega   38.00  104.00   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 55

 13 omega   37.00  178.60   1.2000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -12.0000  150.0000 118

 14 omega  -70.00   22.40   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -50.0000  -20.0000 77

 15 omega  -71.00   25.00   1.2000    2.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -38.0000   30.0000 80

 16 omega   23.00  111.80   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 74

 17 omega   33.00   79.80   1.2000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -30.0000 39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0888803000
_diffrn_orient_matrix_UB_12      -0.0456448000
_diffrn_orient_matrix_UB_13      -0.0510583000
_diffrn_orient_matrix_UB_21      0.1190807000
_diffrn_orient_matrix_UB_22      -0.0852474000
_diffrn_orient_matrix_UB_23      0.0311364000
_diffrn_orient_matrix_UB_31      -0.1926204000
_diffrn_orient_matrix_UB_32      -0.0737234000
_diffrn_orient_matrix_UB_33      -0.0043325000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            11382
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.711
_diffrn_reflns_theta_min         3.440
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_description
;
;
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 1347 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.096
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0542
_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^)+(0.0900P)^2^+0.6061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1503
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.977
_reflns_number_gt                3517
_reflns_number_total             3843
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            np5b00051_si_002.cif
_cod_data_source_block           zhangdb_0511
_cod_depositor_comments
'Adding full bibliography for 1520111--1520112.cif.'
_cod_database_code               1520112
_reflns_odcompleteness_completeness 99.95
_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, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Ternary CH refined with riding coordinates:
 C15(H15), C16(H16)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C14(H14A,H14B), C21(H21A,H21B),
 C25(H25A,H25B)
2.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9), C10(H10), C11(H11), C12(H12), C19(H19)
2.e Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2015-05-11
_olex2_submission_special_instructions 'No special instructions were received'