Concise Syntheses of Bridged Morpholines
Golding, Bernard Thomas; Pickles, James; Zaytsev, Andrey; Harnor, Suzannah; Henderson, Alistair; Alyasiri, Mohammed; Waddell, Paul G.; Cano, Celine; Griffin, Roger; RSC Adv.  (2016) –; doi:10.1039/C6RA08737J

data_7225351
_publ_section_title
;
 Concise Syntheses of Bridged Morpholines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C6RA08737J
_journal_year                    2016
_chemical_formula_moiety         '0.5(C7 H9.36 O5), 0.5(C7 H8.64 O5), H4 N'
_chemical_formula_sum            'C7 H13 N O5'
_chemical_formula_weight         191.18
_chemical_name_systematic
'Diammonium (2R,6S)-tetrahydro-2H-pyran-2,6-dicarboxylate.(2R,6S)-tetrahydro-2H-pyran-2,6-dicarboxylic acid'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2016-04-01 deposited with the CCDC.
2016-05-26 downloaded from the CCDC.
;
_cell_angle_alpha                101.468(3)
_cell_angle_beta                 96.993(3)
_cell_angle_gamma                98.349(3)
_cell_formula_units_Z            4
_cell_length_a                   6.9141(2)
_cell_length_b                   9.3897(3)
_cell_length_c                   14.4781(5)
_cell_measurement_reflns_used    7648
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      66.7850
_cell_measurement_theta_min      3.1400
_cell_volume                     900.35(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector_area_resol_mean 10.3968
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
  1 omega   13.00  104.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905   57.0000 -120.0000 91

  2 omega  -24.00   72.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -77.0000   90.0000 96

  3 omega  -24.00   48.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -57.0000  -60.0000 72

  4 omega   96.00  122.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  123.8262 26

  5 omega   75.00  132.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -156.0984 57

  6 omega  116.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 56

  7 omega   10.00   51.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -93.0000 -156.0984 41

  8 omega   97.00  123.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 26

  9 omega  127.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 45

 10 omega   62.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 33

 11 omega   18.00   43.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 25

 12 omega   64.00   93.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   30.0000 29

 13 omega   41.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  -90.0000 26

 14 omega   40.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000   60.0000 26

 15 omega   34.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -45.0000   90.0000 32

 16 omega   62.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000   30.0000 28

 17 omega   52.00  105.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000 -150.0000 53

 18 omega   32.00   95.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000  120.0000 63

 19 omega   25.00   52.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000 -120.0000 27

 20 omega   23.00   49.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000 -125.0000 -150.0000 26

 21 omega   35.00   79.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   15.0000  -60.0000 44

 22 omega   64.00  133.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000    0.0000 69

 23 omega   20.00   46.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

 24 omega   78.00  104.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000    0.0000 26

 25 omega   22.00   58.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -94.0000  -30.0000 36

 26 omega   78.00  121.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -61.0000  120.0000 43

 27 omega   83.00  109.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -89.0000   75.5260 26

 28 omega   22.00   66.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000    0.0000 44

 29 omega   10.00   77.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000  123.8262 67

 30 omega   81.00  120.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -91.0000  -48.8970 39

 31 omega -120.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -77.0000 -120.0000 112

 32 omega -116.00  -12.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -57.0000   90.0000 104

 33 omega -120.00   -8.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5905  -77.0000    0.0000 112

 34 omega  -34.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -38.0000  -30.0000 102

 35 omega  -34.00   68.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5905  -38.0000 -150.0000 102

 36 omega   63.00  168.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000 -150.0000 105

 37 omega   63.00  171.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   30.0000  150.0000 108

 38 omega   60.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000  -90.0000 112

 39 omega   60.00  172.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   77.0000   60.0000 112
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.2011152000
_diffrn_orient_matrix_UB_12      0.0520423000
_diffrn_orient_matrix_UB_13      -0.0114890000
_diffrn_orient_matrix_UB_21      0.1071215000
_diffrn_orient_matrix_UB_22      0.1614471000
_diffrn_orient_matrix_UB_23      0.0216614000
_diffrn_orient_matrix_UB_31      0.0068984000
_diffrn_orient_matrix_UB_32      -0.0113880000
_diffrn_orient_matrix_UB_33      -0.1071383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12629
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.873
_diffrn_reflns_theta_min         3.153
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.036
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+0.3475P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0843
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2906
_reflns_number_total             3184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra08737j2.cif
_cod_data_source_block           rjg150005_fa
_cod_original_cell_volume        900.34(5)
_cod_database_code               7225351
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C7 H16 N2 O5'
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H,H) groups
2. Restrained distances
 O10-H10 \\sim O2-H2
 with sigma of 0.02
 O8-H8 \\sim O5-H5
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uiso(H2) = Uiso(H10)
Uiso(H5) = Uiso(H8)
4. Others
 Sof(H10)=1-FVAR(1)
 Sof(H2)=FVAR(1)
 Sof(H8)=1-FVAR(2)
 Sof(H5)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C1(H1), C5(H5A), C8(H8A), C12(H12)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B)
;
_shelx_res_checksum              21888
_olex2_submission_special_instructions 'No special instructions were received'
_solvent_exptl_crystal_recrystallization_method Water