Practical Synthesis of Chiral 2-Morpholine: (4-Benzylmorpholin-2-(S)-yl)-(tetrahydropyran-4-yl)methanone Mesylate, a Useful Pharmaceutical Intermediate
Kopach, Michael E.; Singh, Utpal K.; Kobierski, Michael E.; Trankle, William G.; Murray, Michael M.; Pietz, Mark A.; Forst, Mindy B.; Stephenson, Gregory A.; Mancuso, Vincent; Giard, Thierry; Vanmarsenille, Michel; DeFrance, Thierry; Organic Process Research & Development 13 (2009) 209–; doi:10.1021/op800247w

data_1504318
_publ_section_title
;
 Practical Synthesis of Chiral 2-Morpholine:
 (4-Benzylmorpholin-2-(S)-yl)-(tetrahydropyran-4-yl)methanone Mesylate, a
 Useful Pharmaceutical Intermediate
;
_journal_issue                   2
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              209
_journal_paper_doi               10.1021/op800247w
_journal_volume                  13
_journal_year                    2009
_chemical_formula_sum            'C21 H33 N O7 S'
_chemical_formula_weight         443.54
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.0017(2)
_cell_length_b                   12.0689(3)
_cell_length_c                   29.9339(8)
_cell_measurement_reflns_used    2905
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      64.20
_cell_measurement_theta_min      2.95
_cell_volume                     2168.23(11)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_sigmaI/netI    0.0694
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            8316
_diffrn_reflns_theta_full        64.54
_diffrn_reflns_theta_max         64.54
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.7282
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platy
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(4)
_refine_ls_extinction_coef       0.0000(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3144
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0608
_refine_ls_shift/su_max          4.391
_refine_ls_shift/su_mean         0.023
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0835P)^2^+2.3598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1650
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                2490
_reflns_number_total             3144
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op800247w_si_003.cif
_cod_data_source_block           08046xm
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-07-12

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1504318