The Use of Co-crystals for the Determination of Absolute Stereochemistry: An Alternative to Salt Formation
Kevin S. Eccles; Rebecca E. Deasy; László Fábián; Anita R. Maguire; Simon E. Lawrence; Journal of Organic Chemistry 76 (2011) 1159–1162; doi:10.1021/jo102148p

data_4026049
_publ_contact_author_address
;Department of Chemistry 
Analytical and Biological Chemistry Research Facility
University College Cork
Cork
Ireland
;
_publ_contact_author_email       s.lawrence@ucc.ie
_publ_contact_author_fax         +353(21)4274097
_publ_contact_author_name        'Simon E. Lawrence'
_publ_contact_author_phone       +353(21)4903143
_publ_section_title
;
 The Use of Co-crystals for the Determination of Absolute Stereochemistry:
 An Alternative to Salt Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1159
_journal_page_last               1162
_journal_paper_doi               10.1021/jo102148p
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C11 H14 O2, C6 H6 N2 O'
_chemical_formula_sum            'C17 H20 N2 O3'
_chemical_formula_weight         300.35
_chemical_melting_point          336(1)
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.1-2'
_cell_angle_alpha                84.990(4)
_cell_angle_beta                 85.314(4)
_cell_angle_gamma                83.194(4)
_cell_formula_units_Z            2
_cell_length_a                   5.5847(9)
_cell_length_b                   7.8959(12)
_cell_length_c                   17.784(3)
_cell_measurement_reflns_used    3408
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      25.3068
_cell_measurement_theta_min      2.7656
_cell_volume                     773.7(2)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'Bruker Instrument Service v2009, 7, 0, 0'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX DUO'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16279
_diffrn_reflns_theta_full        26.04
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2987
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.127
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0924P)^2^+0.6708P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1810
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                2251
_reflns_number_total             2987
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102148p_si_007.cif
_cod_data_source_block           Compound_2c_Racemic
_cod_database_code               4026049