Total Synthesis of (±)-Grandilodine B.
Wang, Chunyu; Wang, Zhonglei; Xie, Xiaoni; Yao, Xiaotong; Li, Guang; Zu, Liansuo; Organic letters 19 (2017) 1828–1830; doi:10.1021/acs.orglett.7b00591

data_1545573
_publ_section_title
;
 Total Synthesis of (+-)-Grandilodine B.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1828
_journal_page_last               1830
_journal_paper_doi               10.1021/acs.orglett.7b00591
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H25 N3 O5, H2 O'
_chemical_formula_sum            'C24 H27 N3 O6'
_chemical_formula_weight         453.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-11-22
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 96.517(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4886(7)
_cell_length_b                   20.6885(18)
_cell_length_c                   10.5508(7)
_cell_measurement_reflns_used    2794
_cell_measurement_temperature    107.1
_cell_measurement_theta_max      29.1648
_cell_measurement_theta_min      2.9480
_cell_volume                     2274.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_diffrn_ambient_temperature      107.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega   41.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827   77.0000  -30.0000 46

  2 omega   -3.00   69.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827   77.0000  -90.0000 72

  3 omega  -40.00  -13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -15.9046   77.0000   30.0000 27

  4 omega    2.00   36.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827  -37.0000   90.0000 34

  5 omega  -18.00   62.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       20.9827 -101.0000 -174.0000 80
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0224600000
_diffrn_orient_matrix_UB_12      -0.0179242000
_diffrn_orient_matrix_UB_13      -0.0554441000
_diffrn_orient_matrix_UB_21      -0.0088200000
_diffrn_orient_matrix_UB_22      -0.0274177000
_diffrn_orient_matrix_UB_23      0.0384465000
_diffrn_orient_matrix_UB_31      -0.0637247000
_diffrn_orient_matrix_UB_32      0.0101410000
_diffrn_orient_matrix_UB_33      0.0060126000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10461
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.07
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4462
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+0.6670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                3388
_reflns_number_total             4462
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b00591_si_002.cif
_cod_data_source_block           exp_4663
_cod_depositor_comments          'Adding full bibliography for 1545573.cif.'
_cod_database_code               1545573
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32