Flueggether A and Virosinine A, Anti-HIV Alkaloids from Flueggea virosa.
Zhang, Hua; Zhu, Kong-Kai; Han, Ying-Shan; Luo, Cheng; Wainberg, Mark A.; Yue, Jian-Min; Organic letters 17 (2015) 6274–6277; doi:10.1021/acs.orglett.5b03320

data_1555483
_publ_section_title
;
 Flueggether A and Virosinine A, Anti-HIV Alkaloids from Flueggea virosa.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6274
_journal_page_last               6277
_journal_paper_doi               10.1021/acs.orglett.5b03320
_journal_volume                  17
_journal_year                    2015
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C25 H30 N2 O5'
_chemical_formula_sum            'C25 H30 N2 O5'
_chemical_formula_weight         438.51
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-11-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.7500(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.73000(10)
_cell_length_b                   13.8357(2)
_cell_length_c                   9.11730(10)
_cell_measurement_reflns_used    5959
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      68.97
_cell_measurement_theta_min      4.86
_cell_volume                     1098.88(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      140.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8354
_diffrn_reflns_point_group_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         69.792
_diffrn_reflns_theta_min         4.861
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.5698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1338 before and 0.0493 after correction.
The Ratio of minimum to maximum transmission is 0.7564.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Flack x determined using 1555 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0666P)^2^+0.1239P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0985
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_full    0.829
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                3656
_reflns_number_total             3705
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b03320_si_002.cif
_cod_data_source_block           cu_dm13405_0m
_cod_database_code               1555483
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Fixed Sof: H3'A(0.7) H3'B(0.7) H3'C(0.3) H3'D(0.3) C4'(0.7) H4'A(0.7)
 H4'B(0.7) C4"(0.3) H4"A(0.3) H4"B(0.3) H5'A(0.7) H5'B(0.7) H5'C(0.3) H5'D(0.3)
3.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7), C8(H8), C2'(H2'), C7'(H7'), C15'(H15')
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C9(H9A,H9B), C15(H15A,
 H15B), C3'(H3'A,H3'B), C3'(H3'C,H3'D), C4'(H4'A,H4'B), C4"(H4"A,H4"B),
 C5'(H5'A,H5'B), C5'(H5'C,H5'D), C8'(H8'A,H8'B), C14'(H14A,H14B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12'(H12')
;
_shelx_res_checksum              54821
_shelx_hkl_checksum              79713
_olex2_submission_special_instructions 'No special instructions were received'