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_7151514
_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_formula_moiety         ' C50 H66 N2 O4 '
_chemical_formula_sum            'C25 H33 N O2'
_chemical_formula_weight         379.54
_chemical_melting_point          ?
_chemical_name_systematic
;
tert-butyl(1RS,2SR,3RS)-3-methyl-2-(N,N-dibenzylamino)-
cyclopentane-1-carboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             02-11-05
_audit_creation_method           CRYSTALS
_cell_angle_alpha                96.03(1)
_cell_angle_beta                 95.87(1)
_cell_angle_gamma                112.820(7)
_cell_formula_units_Z            4
_cell_length_a                   11.289(1)
_cell_length_b                   11.4013(8)
_cell_length_c                   19.344(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      27
_cell_measurement_theta_min      13
_cell_volume                     2254.2(6)
_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 (Watkin, Prout & Pearce, 1996)
;
_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)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type  '  Enraf-Nonius CAD4 '
_diffrn_measurement_method       2\q/\w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            8364
_diffrn_reflns_theta_max         72.00
_diffrn_reflns_theta_min         0.00
_diffrn_standards_interval_time  3600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '\y scan'
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.12
_exptl_crystal_density_meas      ?
_exptl_crystal_description       ' plate '
_exptl_crystal_F_000             824.0
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.31
_refine_ls_extinction_coef       235.5(355)
_refine_ls_extinction_method     'Larson 1970 Crystallographic Computing eq 22'
_refine_ls_goodness_of_fit_ref   1.0356
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         4360
_refine_ls_R_factor_gt           0.0596
_refine_ls_shift/su_max          0.016594
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Chebychev polynomial with 3 parameters, Caruthers and Watkin, 1979
2.27, 1.51, 1.50
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0669
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                4360
_reflns_number_total             7981
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            b306935b.txt
_cod_data_source_block           CRYSTALS_cif_b
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic ' changed to 'triclinic'
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        2254.06
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        ' C50 H66 N2 O4 '
_cod_database_code               7151514