Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic Transamination and Crystallization-Induced Dynamic Resolution
Chung, John Y. L.; Marcune, Benjamin; Strotman, Hallena R.; Petrova, Rositza I.; Moore, Jeffrey C.; Dormer, Peter G.; Organic Process Research & Development 19 (2015) 1418–; doi:10.1021/acs.oprd.5b00259

data_1532833
_publ_section_title
;
 Synthesis of ((3R,6R)-6-Methylpiperidin-3-yl)methanol via Biocatalytic
 Transamination and Crystallization-Induced Dynamic Resolution
;
_journal_issue                   10
_journal_name_full               'Organic Process Research &amp; Development'
_journal_page_first              1418
_journal_paper_doi               10.1021/acs.oprd.5b00259
_journal_volume                  19
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C14 H16 N, C7 H10 N O3, H2 O'
_chemical_formula_sum            'C21 H28 N2 O4'
_chemical_formula_weight         372.458
_chemical_name_systematic
;
dibenzylammonium (3R,6R)-6-methyl-2-oxopiperidine
-3-carboxylate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_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_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.1
_audit_creation_date             2010-05-19
_audit_creation_method           'merge of exptl & shelxl CIFs via mrlcif'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   8.7278(3)
_cell_length_b                   9.6635(4)
_cell_length_c                   46.6791(18)
_cell_measurement_radiation      'Cu K\a'
_cell_measurement_reflns_used    5855
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.4567
_cell_measurement_theta_min      3.7846
_cell_volume                     3937.0(3)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_molecular_graphics
;
ORTEP3 (Johnson,2000), PLATON (Spek,1990),
PSPLUTO (local version of Motherwell's program)
;
_computing_publication_material  'locally developed programs'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_environment      'N2 gas'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 10.4752
_diffrn_detector_type            'Oxford Diffraction Ruby CCD'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
datacollection start_time: 2010-May-17 15:59:50
1 omega   18.00  117.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1267   38.0000  -30.0000 99
  2 omega   56.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       41.1267 -125.0000   60.0000 37
  3 omega  114.00  174.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   60.0000 60
  4 omega   33.00   99.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000   60.0000 66
  5 omega   20.00   62.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -30.0000 42
  6 omega   22.00   70.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000    0.0000 48
  7 omega   20.00   48.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000  -60.0000 28
  8 omega   32.00   59.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -55.0000 -167.0000 27
  9 omega  102.00  156.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 54
 10 omega   16.00  100.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000  -90.0000 84
 11 omega   19.00   93.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -77.0000   90.0000 74
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction Gemini R Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_measurement_specimen_support 'micromount / oil'
_diffrn_orient_matrix_UB_11      -0.0029545000
_diffrn_orient_matrix_UB_12      0.0112850000
_diffrn_orient_matrix_UB_13      0.0328725000
_diffrn_orient_matrix_UB_21      -0.1331178000
_diffrn_orient_matrix_UB_22      0.1043741000
_diffrn_orient_matrix_UB_23      -0.0020284000
_diffrn_orient_matrix_UB_31      -0.1160527000
_diffrn_orient_matrix_UB_32      -0.1200620000
_diffrn_orient_matrix_UB_33      0.0014754000
_diffrn_radiation_collimation    '300 micron, focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       54
_diffrn_reflns_limit_l_min       -55
_diffrn_reflns_number            15078
_diffrn_reflns_theta_full        66.57
_diffrn_reflns_theta_max         66.4567
_diffrn_reflns_theta_min         3.7846
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_power             40
_diffrn_source_size              '0.4 x 12 mm fine focus'
_diffrn_source_target            Cu
_diffrn_source_type              'Oxford Diffraction Enhance Ultra'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.7047
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    none
_exptl_crystal_description       'thin lathe'
_exptl_crystal_F_000             1600
_exptl_crystal_recrystallization_method
;
Recrystallized by solvent evaporation from acetonitrile 
and water
;
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.016
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881; Hooft, Straver, and Spek J. Appl. Cryst. (2008) 41, 96-103'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.00137(16)
_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   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         6503
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0507
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0755P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                5486
_reflns_number_total             6503
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op5b00259_si_002.cif
_cod_data_source_block           MDF037
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1532833.cif.
;
_cod_database_code               1532833
_chemical_formula_unitcell_mrl   'C168 H224 N16 O32'
_cell_formula_units_zprime_mrl   2
_cell_oxdiff_angle_alpha         89.805(3)
_cell_oxdiff_angle_beta          90.016(3)
_cell_oxdiff_angle_gamma         90.013(4)
_cell_oxdiff_length_a            8.7221(4)
_cell_oxdiff_length_b            9.6595(4)
_cell_oxdiff_length_c            46.7292(19)
_cell_oxdiff_measurement_reflns_used 5855
_cell_oxdiff_volume              3937.0(3)
_symmetry_space_group_name_mrl   P2_12_12_1
_diffrn_reflns_numb_unique_mrl   6503
_refine_atoms_aniso_mrl          54
_refine_atoms_nonh_mrl           54
_refine_atoms_total_mrl          110
_refine_diff_density_near_model_atom '1.53 A from H1G'
_refine_ls_abs_structure_hooft   0.49(11)
_reflns_odcompleteness_completeness 93.16
_reflns_odcompleteness_iscentric 0
_reflns_odcompleteness_theta     66.49