L-Proline Nitrate: A Recyclable and Green Catalyst for the Synthesis of Highly Functionalized Piperidines
Agrawal, Nikita R.; Bahekar, Sandeep P.; Sarode, Prashant B.; Zade, Sanjio S.; Chandak, Hemant S.; RSC Adv.  (2015) –; doi:10.1039/C5RA08022C

data_7220494
_publ_section_title
;
 L-Proline Nitrate: A Recyclable and Green Catalyst for the Synthesis of
 Highly Functionalized Piperidines
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA08022C
_journal_year                    2015
_chemical_formula_moiety         'C38 H42 N2 O8, C38 H40.5 N2 O8'
_chemical_formula_sum            'C76 H84 N4 O16'
_chemical_formula_weight         1309.47
_chemical_name_systematic
;
 ? 
;
_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   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-11-12
_audit_creation_method
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_audit_update_record
;
2015-02-04 deposited with the CCDC.
2015-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                111.929(5)
_cell_angle_beta                 90.797(4)
_cell_angle_gamma                91.318(4)
_cell_formula_units_Z            2
_cell_length_a                   10.6510(5)
_cell_length_b                   17.5440(10)
_cell_length_c                   19.4237(7)
_cell_measurement_reflns_used    8040
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      24.9690
_cell_measurement_theta_min      1.9030
_cell_volume                     3365.0(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9160
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.832
_diffrn_measured_fraction_theta_max 0.8325
_diffrn_measurement_details
;
  1 omega   21.00   47.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -57.0000 -180.0000 26

  2 omega  -18.00   76.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -99.0000   30.0000 94

  3 omega   -6.00  108.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   77.0000 -180.0000 114

  4 omega  -14.00   12.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   77.0000  -60.0000 26

  5 omega   56.00  109.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074   77.0000  -60.0000 53

  6 omega  -17.00   53.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -99.0000  -60.0000 70

  7 omega  -52.00   29.00   1.0000   70.0000
omega____ theta____ kappa____ phi______ frames
    -       27.5074  -38.0000   60.0000 81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0085334000
_diffrn_orient_matrix_UB_12      -0.0415484000
_diffrn_orient_matrix_UB_13      -0.0234268000
_diffrn_orient_matrix_UB_21      0.0051073000
_diffrn_orient_matrix_UB_22      -0.0108527000
_diffrn_orient_matrix_UB_23      0.0316121000
_diffrn_orient_matrix_UB_31      -0.0658855000
_diffrn_orient_matrix_UB_32      -0.0075627000
_diffrn_orient_matrix_UB_33      -0.0015498000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16917
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.91
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75690
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33c (release 11-04-2014 CrysAlis171 .NET)
(compiled Apr 11 2014,15:12:41)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'whitish colourless'
_exptl_crystal_colour_modifier   whitish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     891
_refine_ls_number_reflns         9972
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1172P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.1855
_reflns_number_gt                6987
_reflns_number_total             9972
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ra08022c2.cif
_cod_data_source_block           ssz-aa-pf_twin1_hklf4
_cod_original_cell_volume        3365.1(3)
_cod_database_code               7220494
_chemical_oxdiff_formula         C38N2O8H39
_diffrn_oxdiff_twin_integration_method simultaneous