Enantiopure synthesis of 7-(1-pyrindanyl)propargyl ethers as rasagiline analogues via chemical or enzymatic resolution of 1-pyrindan-7-ol
Sousa, Carlos A. D.; Sampaio-Dias, Ivo E.; Rizzo-Aguiar, Fabio; Garcia-Mera, Xerardo; Rodríguez-Borges, José E.; RSC Adv. 5 (2015) 104509–; doi:10.1039/C5RA24868J

data_7223455
_publ_section_title
;
 Enantiopure synthesis of 7-(1-pyrindanyl)propargyl ethers as rasagiline
 analogues via chemical or enzymatic resolution of 1-pyrindan-7-ol
;
_journal_issue                   126
_journal_name_full               'RSC Adv.'
_journal_page_first              104509
_journal_paper_doi               10.1039/C5RA24868J
_journal_volume                  5
_journal_year                    2015
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C19 H28 N2 O4'
_chemical_formula_sum            'C19 H28 N2 O4'
_chemical_formula_weight         348.43
_chemical_name_systematic        XEBOCA
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/cc1j4flp
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2015-05-29T19:20:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-06 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.959(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.1067(5)
_cell_length_b                   8.7283(3)
_cell_length_c                   11.1168(5)
_cell_measurement_reflns_used    9865
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.03
_cell_measurement_theta_min      3.08
_cell_measurement_wavelength     0.71073
_cell_volume                     984.83(7)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_orient_matrix_UB_11      0.096071
_diffrn_orient_matrix_UB_12      0.024616
_diffrn_orient_matrix_UB_13      0.043927
_diffrn_orient_matrix_UB_21      -0.001476
_diffrn_orient_matrix_UB_22      -0.02105
_diffrn_orient_matrix_UB_23      0.087813
_diffrn_orient_matrix_UB_31      0.021802
_diffrn_orient_matrix_UB_32      -0.109897
_diffrn_orient_matrix_UB_33      -0.006981
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            46898
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_reduction_process
;
        Scaled and merged with Sortav
        R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
        R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.196
_diffrn_reflns_theta_min         2.005
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2806 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     234
_refine_ls_number_reflns         7403
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0543P)^2^+0.0652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.09
_refine_ls_wR_factor_ref         0.094
_reflns_Friedel_coverage         0.874
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                6677
_reflns_number_total             7403
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra24868j2.cif
_cod_data_source_block           shelx
_cod_database_code               7223455
_shelx_estimated_absorpt_t_min   0.937
_shelx_estimated_absorpt_t_max   0.986
_shelx_res_checksum              40258