New building blocks for iminosugars: a concise synthesis of polyhydroxylated N-alkoxypiperidines through an intramolecular azepine ring contraction
Barnes, Korry L.; Chen, Kelly; Catalano, Vincent J.; Jeffrey, Christopher S.; Organic Chemistry Frontiers 2 (2015) 497–; doi:10.1039/C4QO00330F

data_1553066
_publ_section_title
;
 New building blocks for iminosugars: a concise synthesis of
 polyhydroxylated N-alkoxypiperidines through an intramolecular azepine
 ring contraction
;
_journal_issue                   5
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              497
_journal_paper_doi               10.1039/C4QO00330F
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety         'C13 H17 N O3'
_chemical_formula_sum            'C13 H17 N O3'
_chemical_formula_weight         235.27
_chemical_name_systematic
;
(2RS, 3RS)-N-phenylmethoxy-2-hydroxymethyl-3-hydroxy-1,2,3,6-tetrahydropyridine  
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_audit_update_record
;
2014-10-08 deposited with the CCDC.
2015-03-13 downloaded from the CCDC.
;
_cell_angle_alpha                106.4607(7)
_cell_angle_beta                 101.6175(7)
_cell_angle_gamma                100.1738(7)
_cell_formula_units_Z            4
_cell_length_a                   9.9549(4)
_cell_length_b                   11.3328(5)
_cell_length_c                   11.8818(5)
_cell_measurement_reflns_used    4823
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.174
_cell_measurement_theta_min      2.192
_cell_volume                     1219.60(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.65
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23662
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         1.854
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0517 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.9654. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            Clear
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       Block
_exptl_crystal_F_000             504
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.072
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0367
_refine_ls_shift/su_max          0.175
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0273P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0727
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3483
_reflns_number_total             5015
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4qo00330f2.cif
_cod_data_source_block           klb009_0m
_cod_depositor_comments
;

2022-05-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C13 H17 N O3)'
_cod_original_formula_sum        'C26 H34 N2 O6'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     470.55
_cod_database_code               1553066
_shelxl_version_number           2013-4
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.986
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H14A(0.029) H14B(0.029) H15(0.031) H16(0.03) H17(0.024)
 H18(0.022) H19A(0.026) H19B(0.026) H20A(0.028) H20B(0.028) H22(0.035)
 H23(0.045) H24(0.046) H25(0.04) H26(0.03) H1A(0.03) H1B(0.03) H2(0.036)
 H3(0.038) H4A(0.031) H5A(0.026) H6A(0.033) H6B(0.033) H7A(0.036) H7B(0.036)
 H9(0.033) H10(0.034) H11(0.033) H12(0.033) H13(0.028) H1(0.045) H2A(0.065)
 Fixed X: H14A(0.3431) H14B(0.1777) H15(0.2632) H16(0.1516) H17(-0.0057)
 H18(0.0141) H19A(0.1147) H19B(0.048) H20A(0.4253) H20B(0.3175) H22(0.2067)
 H23(0.2006) H24(0.3232) H25(0.4554) H26(0.461) H1A(0.2342) H1B(0.0812)
 H2(0.1198) H3(0.2566) H4A(0.4566) H5A(0.4378) H6A(0.4832) H6B(0.4166)
 H7A(0.1741) H7B(0.0606) H9(0.3978) H10(0.4288) H11(0.2319) H12(0.0046) H13(-
 0.0266) H1(0.2377) H2A(0.612)
 Fixed Y: H14A(0.9979) H14B(0.9827) H15(1.0693) H16(0.9228) H17(0.7413)
 H18(0.7911) H19A(0.5659) H19B(0.6043) H20A(0.7941) H20B(0.6556) H22(0.559)
 H23(0.5568) H24(0.7325) H25(0.9108) H26(0.9139) H1A(0.0054) H1B(0.0351) H2(-
 0.0221) H3(0.1261) H4A(0.2609) H5A(0.1685) H6A(0.3447) H6B(0.425) H7A(0.3455)
 H7B(0.214) H9(0.3369) H10(0.3821) H11(0.3603) H12(0.2916) H13(0.2422)
 H1(0.3589) H2A(0.4703)
 Fixed Z: H14A(0.3874) H14B(0.3784) H15(0.2232) H16(0.0413) H17(0.0468)
 H18(0.2502) H19A(0.1807) H19B(0.2943) H20A(0.4613) H20B(0.4021) H22(0.5312)
 H23(0.7257) H24(0.8953) H25(0.8714) H26(0.6774) H1A(0.6559) H1B(0.6436)
 H2(0.8224) H3(0.9956) H4A(0.9772) H5A(0.7732) H6A(0.7053) H6B(0.8045)
 H7A(0.6153) H7B(0.5352) H9(0.4891) H10(0.3155) H11(0.159) H12(0.1768)
 H13(0.3487) H1(0.9199) H2A(0.9247)
;