Total facial selectivity of a d-erythrosyl aromatic imine in [4π + 2π] cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines.
Ferreira, Juliana; Duarte, Vera C. M.; Noro, Jennifer; Gil Fortes, António; Alves, Maria J.; Organic & biomolecular chemistry 14 (2016) 2930–2937; doi:10.1039/c5ob02594j

data_7154957
_publ_section_title
;
 Total facial selectivity of a d-erythrosyl aromatic imine in [4\p + 2\p]
 cycloadditions; synthesis of 2-alkylpolyol 1,2,3,4-tetrahydroquinolines.
;
_journal_issue                   10
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2930
_journal_page_last               2937
_journal_paper_doi               10.1039/c5ob02594j
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C23 H25 N O4'
_chemical_formula_sum            'C23 H25 N O4'
_chemical_formula_weight         379.44
_chemical_name_systematic        JF95
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-04-13T16:37:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-04-16 deposited with the CCDC.
2016-02-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.97(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   31.53(3)
_cell_length_b                   4.779(5)
_cell_length_c                   12.837(11)
_cell_measurement_reflns_used    385
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.79
_cell_measurement_theta_min      3.23
_cell_measurement_wavelength     0.71073
_cell_volume                     1899(3)
_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 0.99
_diffrn_measured_fraction_theta_max 0.99
_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      0.012086
_diffrn_orient_matrix_UB_12      -0.179233
_diffrn_orient_matrix_UB_13      -0.022036
_diffrn_orient_matrix_UB_21      -0.027979
_diffrn_orient_matrix_UB_22      -0.038829
_diffrn_orient_matrix_UB_23      -0.049249
_diffrn_orient_matrix_UB_31      0.010719
_diffrn_orient_matrix_UB_32      0.100749
_diffrn_orient_matrix_UB_33      -0.058182
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2227
_diffrn_reflns_av_unetI/netI     0.1861
_diffrn_reflns_Laue_measured_fraction_full 0.99
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7774
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_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        18.984
_diffrn_reflns_theta_max         18.984
_diffrn_reflns_theta_min         1.316
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.493
_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    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details
;
 Flack x determined using 289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_extinction_coef       0.019(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     261
_refine_ls_number_reflns         1516
_refine_ls_number_restraints     403
_refine_ls_restrained_S_all      0.977
_refine_ls_R_factor_all          0.1306
_refine_ls_R_factor_gt           0.0801
_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^)+(0.0904P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1848
_refine_ls_wR_factor_ref         0.2182
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                995
_reflns_number_total             1516
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02594j1.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7154957.cif.'
_cod_database_code               7154957
_shelx_estimated_absorpt_t_min   0.931
_shelx_estimated_absorpt_t_max   0.998