Practical, general, and systematic method for optical resolution of gem-dihalo- and monohalocyclopropanecarboxylic acids utilizing chiral 1,1′-binaphtholmonomethyl ethers: Application to the synthesis of three chiral pesticides
Yasukochi, Hiroaki; Atago, Takayuki; Tanaka, Akihiro; Nakatsuji, Hidefumi; Yoshida, Eri; Kakehi, Akikazu; Nishii, Yoshinori; Tanabe, Yoo; Organic & Biomolecular Chemistry 6 (2008) 540–547; doi:10.1039/b714614k

data_7150813
_publ_section_title
;
 Practical, general, and systematic method for optical resolution of
 gem-dihalo- and monohalocyclopropanecarboxylic acids utilizing chiral
 1,1&#x2032;-binaphtholmonomethyl ethers: Application to the synthesis
 of three chiral pesticides
;
_journal_issue                   3
_journal_name_full               'Organic &amp;  Biomolecular Chemistry'
_journal_page_first              540
_journal_page_last               547
_journal_paper_doi               10.1039/b714614k
_journal_volume                  6
_journal_year                    2008
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C14 H17 Cl2 N O '
_chemical_formula_sum            'C14 H17 Cl2 N O'
_chemical_formula_weight         286.20
_chemical_melting_point          381.5(5)
_chemical_name_common
;
'N-((1S, 3S)-2,2-dichloro-1,3-dimethylcyclopropanecarbonyl)-
(1S)-1-phenylethylam
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 101.08(16)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   9.82(3)
_cell_length_b                   9.82(3)
_cell_length_c                   16.09(3)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      12.0
_cell_measurement_theta_min      10.1
_cell_volume                     1523(7)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'CrystalStructure (Rigaku & RAC 2007)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976)'
_computing_publication_material  'CrystalStructure (Rigaku & RAC 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku AFC5S'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.062
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3825
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             600.00
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.24
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   -0.09(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     332
_refine_ls_number_reflns         3608
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0923P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2149
_reflns_number_gt                1277
_reflns_number_total             3608
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            b714614k.txt
_cod_data_source_block           '_nishii12'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '381-382K' was changed to '381.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1522(7)
_cod_original_formula_sum        'C14 H17 Cl2 N O '
_cod_database_code               7150813