Quantitative chirality sensing of amines and amino alcohols via Schiff base formation with a stereodynamic UV/CD probe.
De Los Santos, Zeus A.; Ding, Ransheng; Wolf, Christian; Organic & biomolecular chemistry 14 (2016) 1934–1939; doi:10.1039/c5ob02529j

data_7154903
_publ_section_title
;
 Quantitative chirality sensing of amines and amino alcohols via Schiff
 base formation with a stereodynamic UV/CD probe.
;
_journal_issue                   6
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1934
_journal_page_last               1939
_journal_paper_doi               10.1039/c5ob02529j
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29
_chemical_name_systematic        N-(2-formylphenyl)-2-naphthamide
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-12-04 deposited with the CCDC.
2016-01-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.4271(14)
_cell_length_b                   3.7892(3)
_cell_length_c                   14.3031(7)
_cell_measurement_reflns_used    3662
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.337
_cell_measurement_theta_min      2.853
_cell_volume                     1323.88(14)
_computing_cell_refinement       'SAINT v. 8.34A, Bruker-AXS'
_computing_data_collection       'APEX 2, Bruker-AXS'
_computing_data_reduction        'SAINT v. 8.34A, Bruker-AXS'
_computing_molecular_graphics    'X-SEED, L.Barbour (1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-Version 2013/1, G.Sheldrick'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0489
_diffrn_reflns_av_unetI/netI     0.0409
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10296
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.296
_diffrn_reflns_theta_min         1.667
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1,G. Sheldrick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile'
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0549P)^2^+0.1559P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0934
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                2148
_reflns_number_total             2423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02529j2.cif
_cod_data_source_block           added_by_encifer
_cod_depositor_comments
'Adding full bibliography for 7154901--7154903.cif.'
_cod_database_code               7154903
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              98635
_shelx_hkl_checksum              75522