Organocatalytic enantioselective total synthesis of (-)-arboricine.
Wanner, Martin J.; Boots, Rowan N. A.; Eradus, Bram; de Gelder, René; van Maarseveen, Jan H.; Hiemstra, Henk; Organic letters 11 (2009) 2579–2581; doi:10.1021/ol900888e

data_1503967
_publ_contact_author
;
        Prof.dr. H. Hiemstra
        Van 't Hoff Institute for Molecular Sciences
        Faculty of Science
        University of Amsterdam
        Nieuwe Achtergracht 129
        1018 WS Amsterdam
        The Netherlands
;
_publ_section_title
;
 Organocatalytic enantioselective total synthesis of (-)-arboricine.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2579
_journal_page_last               2581
_journal_paper_doi               10.1021/ol900888e
_journal_volume                  11
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_sum            'C24 H30 N2 O3'
_chemical_formula_weight         394.50
_chemical_name_systematic
;
 (-)-Arboricine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
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_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-07-27
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_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5509(2)
_cell_length_b                   11.1823(3)
_cell_length_c                   20.0306(3)
_cell_measurement_reflns_used    89
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      69.560
_cell_measurement_theta_min      4.410
_cell_volume                     2139.29(8)
_computing_data_collection
;
Nonius "Collect" program suite (Nonius, 1999)
;
_computing_data_reduction
;
Nonius "EvalCCD" program suite (Duisenberg, 1998)
;
_computing_molecular_graphics
;
PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
CRUNCH (de Gelder et al., 1993),
;
_diffrn_ambient_temperature      208(2)
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_diffrn_measurement_device       'Nonius KappaCCD'
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_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
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_diffrn_reflns_theta_max         69.56
_diffrn_reflns_theta_min         4.41
_diffrn_standards_decay_%        0.000
_diffrn_standards_interval_time  0
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_exptl_absorpt_coefficient_mu    0.642
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_exptl_absorpt_correction_type   multi-scan
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_exptl_crystal_colour            'translucent yellow-brown'
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rough lump'
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_refine_ls_abs_structure_details
;
The absolute configuration assignment was based on 1673 Friedel
pairs used to calculate the Flack parameter
;
_refine_ls_abs_structure_Flack   0.03(15)
_refine_ls_extinction_method     none
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_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         3960
_refine_ls_number_restraints     0
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_refine_ls_R_factor_all          0.0286
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_refine_ls_R_factor_obs          0.0277
_refine_ls_shift/esd_max         0.000
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_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^)+(0.0419P)^2^+0.2741P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0711
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_obs         0.0703
_refine_ls_wR_factor_ref         0.0711
_reflns_number_gt                3855
_reflns_number_observed          3855
_reflns_number_total             3960
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol900888e_si_002.cif
_cod_data_source_block           ARBORI
_cod_depositor_comments
;
The following automatic conversions were performed:
'_publ_contact_autor' tag replaced with '_publ_contact_author'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26 (32
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (49 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               1503967