The First Enantioselective Total Synthesis of (-)-trans-Dihydronarciclasine.
Varró, Gábor; Hegedűs, László; Simon, András; Balogh, Attila; Grün, Alajos; Leveles, Ibolya; Vértessy, Beáta G; Kádas, István; Journal of natural products 80 (2017) 1909–1917; doi:10.1021/acs.jnatprod.7b00208

data_1546459
_publ_section_title
;
 The First Enantioselective Total Synthesis of
 (-)-trans-Dihydronarciclasine.
;
_journal_issue                   6
_journal_name_full               'Journal of natural products'
_journal_page_first              1909
_journal_page_last               1917
_journal_paper_doi               10.1021/acs.jnatprod.7b00208
_journal_volume                  80
_journal_year                    2017
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C14 H15 N O7'
_chemical_formula_sum            'C14 H15 N O7'
_chemical_formula_weight         309.27
_chemical_name_systematic
;
(3S,4R,5R)-3-hydroxy-5-(7-methoxybenzo[d][1,3]dioxol-5-yl)-4-nitrocyclohexan-1-one

;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-03-08 deposited with the CCDC.
2017-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 92.5859(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.21152(11)
_cell_length_b                   5.70278(14)
_cell_length_c                   19.9440(3)
_cell_measurement_reflns_used    6553
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      70.8220
_cell_measurement_theta_min      4.4150
_cell_volume                     705.76(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9865
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0957244000
_diffrn_orient_matrix_UB_12      -0.0788273000
_diffrn_orient_matrix_UB_13      0.0689495000
_diffrn_orient_matrix_UB_21      -0.2286736000
_diffrn_orient_matrix_UB_22      -0.0481326000
_diffrn_orient_matrix_UB_23      0.0235403000
_diffrn_orient_matrix_UB_31      0.0138148000
_diffrn_orient_matrix_UB_32      -0.2538866000
_diffrn_orient_matrix_UB_33      -0.0258465000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            12353
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         71.01
_diffrn_reflns_theta_min         4.44
_exptl_absorpt_coefficient_mu    1.012
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;

CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.

;
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             324
_exptl_crystal_recrystallization_method recrystallization
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.917
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0381
_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                2329
_reflns_number_total             2577
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            np7b00208_si_003.cif
_cod_data_source_block           exp_634_0306
_cod_database_code               1546459
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_theta     66.97
_reflns_odcompleteness_iscentric 1