Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl (±)-3-methylcyclopentene-1-carboxylate
Bunnage, Mark E.; Chippindale, Ann M.; Davies, Stephen G.; Parkin, Richard M.; Smith, Andrew D.; Withey, Jonathan M.; Organic & Biomolecular Chemistry 1 (2003) 3698–3707; doi:10.1039/b306935b

data_7151515
_publ_section_title
;
 Asymmetric synthesis of (1R,2S,3R)-3-methylcispentacin and
 (1S,2S,3R)-3-methyltranspentacin by kinetic resolution of tert-butyl
 (+-)-3-methylcyclopentene-1-carboxylate
;
_journal_coden_ASTM              OBCRAK
_journal_issue                   21
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              3698
_journal_page_last               3707
_journal_paper_doi               10.1039/b306935b
_journal_volume                  1
_journal_year                    2003
_chemical_absolute_configuration ad
_chemical_compound_source
;
see paper
;
_chemical_formula_moiety         ' C26 H35 N1 O2  '
_chemical_formula_sum            'C26 H35 N O2'
_chemical_formula_weight         393.55
_chemical_melting_point          ?
_chemical_name_systematic
;
tert-butyl(1R,2S,3R,aS)-3-methyl-2-(N-benzylamino)-
cyclopentane-1-carboxylate
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ac'
_symmetry_space_group_name_H-M   'P 21 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
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_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4.00
_cell_length_a                   9.9698(8)
_cell_length_b                   10.8697(9)
_cell_length_c                   21.974(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      12
_cell_volume                     2381.3(5)
_computing_cell_refinement       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 software (Enraf-Nonius, 1989)'
_computing_data_reduction
;
RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994)
;
_computing_molecular_graphics
;
CAMERON
;
_computing_publication_material
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge,
1996)
;
_computing_structure_refinement
;
CRYSTALS Issue 10 (Watkin, Prout, Carruthers & Betteridge,
1996)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
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_diffrn_measured_fraction_theta_max 0.95
_diffrn_measurement_device_type  '  Enraf-Nonius CAD4 '
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_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
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_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
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_exptl_absorpt_correction_type   empirical
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_exptl_crystal_colour            ' colourless '
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_exptl_crystal_description       ' plate '
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_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
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_refine_ls_number_reflns         4273
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_refine_ls_shift/su_max          0.018190
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters (Carruthers and
Watkin, 1979)
2.27, 1.51, 1.50
;
_refine_ls_weighting_scheme      calc
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_reflns_limit_k_min              0
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_reflns_limit_l_min              0
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_reflns_number_total             4600
_reflns_threshold_expression     >3.00\s(I)
_cod_data_source_file            b306935b.txt
_cod_data_source_block           CRYSTALS_cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic ' changed to 'orthorhombic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'EMPIRICAL' changed to
'empirical' according to
'/home/adriana/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1569 2011-02-09 13:29:24Z adriana 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct_Methods' was changed to
'direct'.

'_atom_sites_solution_hydrogens' value 'Geometric' was changed to
'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_cell_volume        2381.28
_cod_original_sg_symbol_H-M      'P 21 2 21 '
_cod_original_formula_sum        ' C26 H35 N1 O2 '
_cod_database_code               7151515