##############################################################################
###                                                                        ###
###           CIF-Access Paper (Acta Crystallographica Section C)          ###
###                                                                        ###
##############################################################################
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# This paper is published electronically in CIF format. It meets the data-   #
# validation criteria for publication in Acta Crystallographica Section C.   #
# The submission has been checked by a Section C Co-editor though the text   #
# in _publ_section_comments is the responsibility of the authors.            #
#                                                                            #
# CIF-access papers are listed in the printed contents pages of an issue of  #
# Acta Crystallographica Section C within two months of acceptance and are   #
# available by email and via the online contents pages for that issue.       #
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# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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# This file may be used for bona fide research purposes within the           #
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data_default
_audit_creation_method     from_MolEN_master_file_using_cif_in
_journal_data_validation_number     IUC9800033
_journal_date_recd_electronic     98-05-20
_journal_date_accepted     98-06-17
_journal_name_full     ?
_journal_year     1998
_journal_volume     C54
_journal_issue     JUL98
_journal_paper_category     CO
_publ_contact_author_name     'Jan W. Bats'
_publ_contact_author_address
;
 Institut für Organische Chemie
 Universität Frankfurt
 Marie-Curie-Strasse 11
 D-60439 Frankfurt am Main
 Germany
;
_publ_contact_author_email     bats@indy2.org.chemie.uni-frankfurt.de
_publ_contact_author_fax     '+49 69 79829128'
_publ_contact_author_phone     '+49 69 79829124'
_publ_section_title
;
 (2S,3R,4R,5R)-2-Benzyl-N-(tert-butoxycarbonyl)-3-hydroxy-
  4,5-dimethylpyrrolidine at 133 K
;
loop_
    _publ_author_name
    _publ_author_address
    'Bats, Jan W.'
;
 Institut für Organische Chemie der Universität Frankfurt
 Marie-Curie-Strasse 11
 D-60439 Frankfurt am Main
 Germany
;
    'Heinrich, Timo'
;
 Institut für Organische Chemie der Universität Frankfurt
 Marie-Curie-Strasse 11
 D-60439 Frankfurt am Main
 Germany
;
    'Reggelin, Michael'
;
 Institut für Organische Chemie der Universität Frankfurt
 Marie-Curie-Strasse 11
 D-60439 Frankfurt am Main
 Germany
;
_publ_section_synopsis
;
 The pyrrolidine ring has a twist conformation with a pseudo-two-
 fold axis passing through the N atom. The crystal packing is
 stabilized by an intermolecular hydrogen bond.
;
_publ_section_abstract
;
 The structure determination of the title compound C₁₈H₂₇NO₃
 was undertaken to establish the relative configuration of the
 chiral centers. The pyrrolidine ring has a twist conformation. The
 crystal packing is stabilized by intermolecular hydrogen bonding.
;
_publ_section_comment
;
 The synthesis of the title compound and a number of isomers has been
 reported by Reggelin and Heinrich ( 1998). A structure determination was
 undertaken to confirm the expected configurations of the chiral centers.
 The pyrrolidine ring has a twist conformation with a pseudo-two-fold axis
 passing through N and the midpoint of the C2-C3 bond. The ring puckering
 parameters defined by Cremer and Pople (1975) are q = 0.393 Å and
 φ = 267 °  . A stereoisomer of the title compound with (2S,3S,4S,5S)-
 configuration reported by Bolte (1997) has an inverted ring conformation
 ( φ = 84°  ). The hydroxyl group is in a pseudo-axial position, methyl
 group C12 is in a pseudo-equatorial position with respect the the five-
 membered ring. The N atom shows a small deviation from planarity
 ( sum of bond angles about the N atom: 357.3° ).
 The hydroxyl group is involved in an intermolecular hydrogen bond to
 atom O2 of a symmetry-related molecule ( symmetry code: -x, y-0.5, 1.5-z ).
 The dimensions of the hydrogen bond are: O1 - H01: 0.83(2) Å, H01 ... O2:
 1.94(2) Å, O1 ... O2: 2.763(1) Å and angle O1 - H01 - O2: 169(1) ° .
 The hydrogen bonds connect the molecules to zig-zag chains in the
 crystallographic b - direction. There are no other significant inter-
 molecular contacts.
;
_publ_section_references
;
+qa0017+Bolte, M. (1997). Acta Cryst. C53, IUC9700028.
Cremer, D. & Pople, J.A. (1975) J. Am. Chem. Soc., 97, 1354-1358.
Fair, C.K. (1990).  MolEN, An Interactive Intelligent System for Crystal
Structure Analysis, User Manual, Enraf -  Nonius, Delft, The Netherlands.
Reggelin, M. & Heinrich, T. (1998) Angew. Chem., in preparation.
Sheldrick, G.M. (1996) SHELXTL. Structure Determination Software Programs.
Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Siemens (1995). SMART and SAINT. Area-Detector Control and Integration
Software. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Zachariasen, W.H. (1967).  Acta Cryst.  23, 558-564.
;
_publ_section_exptl_prep
;
 Crystals were grown from a solution of the title compound in ether/
 n-hexane.
;
data_hei347
_chemical_name_systematic
;
 (2S,3R,4R,5R)-2-benzyl-N-(tert-butyloxycarbonyl)-3-hydroxy-
 4,5-dimethyl-pyrrolidine
;
_chemical_formula_sum     'C18 H27 N O3'
_chemical_formula_structural     ?
_chemical_formula_weight     305.42
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_h-m     'P 21 21 21'
_cell_length_a     11.2771(10)
_cell_length_b     11.3895(11)
_cell_length_c     13.715(2)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1761.6(4)
_cell_formula_units_z     4
_cell_measurement_reflns_used     333
_cell_measurement_theta_min     3
_cell_measurement_theta_max     23
_cell_measurement_temperature     133
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.65
_exptl_crystal_size_mid     0.46
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.152
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     664
_exptl_absorpt_coefficient_mu     0.072
_exptl_absorpt_correction_type     none
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_radiation_type     Mo-K\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device     SIEMENS_SMART
_diffrn_measurement_method     ω
_diffrn_reflns_number     26770
_diffrn_reflns_av_R_equivalents     0.020
_diffrn_reflns_theta_max     29.94
_diffrn_reflns_limit_h_min     -14
_diffrn_reflns_limit_h_max     15
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     488
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     540
_diffrn_standards_decay_%     0.00
_reflns_number_total     2672
_reflns_number_observed     2663
_reflns_observed_criterion     I>0.0\s(I)
_refine_ls_structure_factor_coef     F
_refine_ls_R_factor_obs     0.033
_refine_ls_wR_factor_obs     0.037
_refine_ls_goodness_of_fit_obs     1.475
_refine_ls_number_reflns     2663
_refine_ls_number_parameters     308
_refine_ls_hydrogen_treatment     H_atoms_refined_isotropically
_refine_ls_weighting_scheme     '4Fo^2^/ (\s^2^(Fo^2^) + 0.0009 Fo^4^)'
_refine_ls_shift/esd_max     0.043
_refine_diff_density_max     0.2262
_refine_diff_density_min     -0.1180
_refine_ls_extinction_method     isotropic_(Zachariasen,_1967)
_refine_ls_extinction_coef     0.0000017(5)
_refine_ls_abs_structure_details
;
 The absolute configuration of the compound has been established by
 the known 2S-configuration.
;
_refine_ls_abs_structure_Flack     -0.1(6)
_atom_type_scat_source
                          International_Tables_for_Xray_Crystallography_(Vol.IV)
_computing_data_collection     SMART_(Siemens,_1995)
_computing_cell_refinement     SMART_(Siemens,_1995)
_computing_data_reduction     SAINT_(Siemens,_1995)
_computing_structure_solution     Direct_methods_(SHELXS,_Sheldrick,_1996)
_computing_structure_refinement     LSFM_MolEN_(Fair,_1990)
_computing_molecular_graphics     XP_in_SHELXTL_(Sheldrick,_1996)
_computing_publication_material     BTABLE_PTABLE_CIF_in_MolEN_(Fair,_1990)
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_thermal_displace_type
    _atom_site_calc_flag
    O1 -0.20087(8) 0.54522(7) 0.75808(7) 0.0250(4) Uani ?
    O2 0.08698(8) 0.83851(7) 0.79032(7) 0.0250(4) Uani ?
    O3 0.16754(7) 0.65792(8) 0.82047(7) 0.0236(4) Uani ?
    N -0.02055(8) 0.69245(8) 0.85899(8) 0.0186(4) Uani ?
    C1 -0.03940(10)
                  0.56532(9) 0.87478(9) 0.0174(5) Uani ?
    C2 -0.17360(10)
                  0.55310(10)
                            0.85918(9) 0.0191(5) Uani ?
    C3 -0.22250(10)
                  0.66980(10)
                            0.89675(9) 0.0199(5) Uani ?
    C4 -0.13230(10)
                  0.76020(10)
                            0.85962(9) 0.0185(5) Uani ?
    C5 0.00310(10)
                 0.52710(10)
                           0.97603(9) 0.0209(5) Uani ?
    C6 -0.00040(10)
                  0.39550(10)
                            0.99051(9) 0.0200(5) Uani ?
    C7 0.07020(10)
                 0.32240(10)
                           0.93349(9) 0.0253(6) Uani ?
    C8 0.07010(10)
                 0.20180(10)
                           0.94740(10)
                                     0.0322(6) Uani ?
    C9 0.00030(10)
                 0.15290(10)
                           1.01910(10)
                                     0.0327(6) Uani ?
    C10 -0.07090(10)
                   0.22390(10)
                             1.07590(10)
                                       0.0326(6) Uani ?
    C11 -0.07210(10)
                   0.34470(10)
                             1.06167(9) 0.0254(6) Uani ?
    C12 -0.34990(10)
                   0.69570(10)
                             0.86690(10)
                                       0.0274(6) Uani ?
    C13 -0.12530(10)
                   0.87040(10)
                             0.92240(10)
                                       0.0265(6) Uani ?
    C14 0.07890(10)
                  0.73770(10)
                            0.82004(9) 0.0199(5) Uani ?
    C15 0.27480(10)
                  0.67470(10)
                            0.76002(9) 0.0202(5) Uani ?
    C16 0.33770(10)
                  0.55740(10)
                            0.77300(10)
                                      0.0280(6) Uani ?
    C17 0.34980(10)
                  0.77460(10)
                            0.79940(10)
                                      0.0262(6) Uani ?
    C18 0.23990(10)
                  0.69330(10)
                            0.65420(10)
                                      0.0285(6) Uani ?
    H1 0.0020(10)
                0.5200(10)
                         0.8240(10)
                                  0.019(3) Uiso ?
    H01 -0.1670(10)
                  0.4860(10)
                           0.7360(10)
                                    0.042(4) Uiso ?
    H2 -0.2060(10)
                 0.4880(10)
                          0.8955(9) 0.021(3) Uiso ?
    H3 -0.2160(10)
                 0.6710(10)
                          0.9694(9) 0.015(3) Uiso ?
    H4 -0.1520(10)
                 0.7820(10)
                          0.7949(9) 0.022(3) Uiso ?
    H5B 0.0830(10)
                 0.5520(10)
                          0.9810(10)
                                   0.024(4) Uiso ?
    H5A -0.0460(10)
                  0.5620(10)
                           1.0260(10)
                                    0.029(4) Uiso ?
    H7 0.1180(10)
                0.3550(10)
                         0.8870(10)
                                  0.031(4) Uiso ?
    H8 0.1230(10)
                0.1550(10)
                         0.9080(10)
                                  0.049(5) Uiso ?
    H9 -0.001(2) 0.0670(10)
                          1.0280(10)
                                   0.053(5) Uiso ?
    H10 -0.1230(10)
                  0.1950(10)
                           1.1260(10)
                                    0.038(4) Uiso ?
    H11 -0.1200(10)
                  0.3950(10)
                           1.1020(10)
                                    0.033(4) Uiso ?
    H12A -0.3570(10)
                   0.6950(10)
                            0.7970(10)
                                     0.040(5) Uiso ?
    H12C -0.4050(10)
                   0.6380(10)
                            0.8950(10)
                                     0.054(5) Uiso ?
    H12B -0.3780(10)
                   0.7710(10)
                            0.8940(10)
                                     0.037(4) Uiso ?
    H13C -0.0700(10)
                   0.9350(10)
                            0.8930(10)
                                     0.039(4) Uiso ?
    H13B -0.0940(10)
                   0.8500(10)
                            0.9890(10)
                                     0.035(4) Uiso ?
    H13A -0.2060(10)
                   0.9070(10)
                            0.9270(10)
                                     0.047(5) Uiso ?
    H16B 0.2870(10)
                  0.4960(10)
                           0.7470(10)
                                    0.031(4) Uiso ?
    H16A 0.4100(10)
                  0.5550(10)
                           0.7350(10)
                                    0.044(5) Uiso ?
    H16C 0.3550(10)
                  0.5410(10)
                           0.8420(10)
                                    0.028(4) Uiso ?
    H17A 0.3670(10)
                  0.7570(10)
                           0.8710(10)
                                    0.051(5) Uiso ?
    H17B 0.3090(10)
                  0.8490(10)
                           0.7900(10)
                                    0.037(4) Uiso ?
    H17C 0.4290(10)
                  0.7740(10)
                           0.7630(10)
                                    0.033(4) Uiso ?
    H18B 0.1880(10)
                  0.6320(10)
                           0.6290(10)
                                    0.045(5) Uiso ?
    H18C 0.1960(10)
                  0.7660(10)
                           0.6470(10)
                                    0.029(4) Uiso ?
    H18A 0.3100(10)
                  0.6980(10)
                           0.6130(10)
                                    0.041(5) Uiso ?
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O1 0.0269(4) 0.0221(4) 0.0262(4) 0.0053(4) -0.0068(4) -0.0066(4)
    O2 0.0222(4) 0.0197(4) 0.0359(5) 0.0001(4) 0.0038(4) 0.0077(4)
    O3 0.0169(4) 0.0232(4) 0.0337(4) 0.0022(4) 0.0056(4) 0.0095(4)
    N 0.0171(4) 0.0143(4) 0.0262(5) 0.0008(4) 0.0016(4) 0.0027(4)
    C1 0.0171(5) 0.0137(4) 0.0223(5) -0.0005(4) 0.0006(4) 0.0013(4)
    C2 0.0178(5) 0.0176(5) 0.0224(5) -0.0010(5) -0.0001(5) 0.0006(5)
    C3 0.0169(5) 0.0205(5) 0.0227(5) 0.0004(5) 0.0015(4) -0.0007(5)
    C4 0.0182(5) 0.0166(5) 0.0209(5) 0.0026(4) 0.0008(4) 0.0006(4)
    C5 0.0220(5) 0.0182(5) 0.0227(5) -0.0006(5) -0.0015(5) 0.0001(5)
    C6 0.0220(5) 0.0186(5) 0.0195(5) -0.0005(5) -0.0061(5) 0.0016(5)
    C7 0.0283(6) 0.0259(6) 0.0220(5) 0.0030(6) -0.0028(5) 0.0008(5)
    C8 0.0422(7) 0.0246(6) 0.0322(6) 0.0095(6) -0.0124(6) -0.0060(5)
    C9 0.0499(8) 0.0184(5) 0.0379(7) -0.0046(6) -0.0195(6) 0.0038(6)
    C10 0.0395(7) 0.0293(6) 0.0301(6) -0.0122(6) -0.0077(6) 0.0088(6)
    C11 0.0250(5) 0.0269(6) 0.0244(6) -0.0033(5) -0.0025(5) 0.0023(5)
    C12 0.0174(5) 0.0282(6) 0.0420(7) 0.0025(5) 0.0006(6) -0.0053(6)
    C13 0.0296(6) 0.0189(5) 0.0334(6) 0.0010(5) 0.0035(6) -0.0044(5)
    C14 0.0180(5) 0.0195(5) 0.0225(5) -0.0004(5) 0.0006(5) 0.0023(5)
    C15 0.0147(4) 0.0233(5) 0.0242(5) 0.0008(5) 0.0019(4) 0.0034(5)
    C16 0.0238(5) 0.0275(6) 0.0336(6) 0.0063(5) 0.0015(6) 0.0016(6)
    C17 0.0197(5) 0.0269(6) 0.0340(6) -0.0010(5) -0.0018(5) 0.0011(6)
    C18 0.0271(6) 0.0329(7) 0.0258(6) 0.0022(6) -0.0015(5) 0.0020(6)
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C2 1.423(2) ?
    O2 C14 1.2210(10)
                    ?
    O3 C14 1.3520(10)
                    ?
    O3 C15 1.4790(10)
                    ?
    N C1 1.4790(10)
                  ?
    N C4 1.4780(10)
                  ?
    N C14 1.345(2) ?
    C1 C2 1.535(2) ?
    C1 C5 1.532(2) ?
    C2 C3 1.529(2) ?
    C3 C4 1.535(2) ?
    C3 C12 1.523(2) ?
    C4 C13 1.524(2) ?
    C5 C6 1.512(2) ?
    C6 C7 1.392(2) ?
    C6 C11 1.393(2) ?
    C7 C8 1.387(2) ?
    C8 C9 1.377(2) ?
    C9 C10 1.381(2) ?
    C10 C11 1.389(2) ?
    C15 C16 1.523(2) ?
    C15 C17 1.517(2) ?
    C15 C18 1.519(2) ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle
    _geom_angle_publ_flag
    C14 O3 C15 121.03(9) ?
    C1 N C4 112.84(9) ?
    C1 N C14 123.60(9) ?
    C4 N C14 120.83(9) ?
    N C1 C2 102.14(9) ?
    N C1 C5 111.47(9) ?
    C2 C1 C5 114.20(10)
                      ?
    O1 C2 C1 110.76(9) ?
    O1 C2 C3 107.76(9) ?
    C1 C2 C3 103.26(9) ?
    C2 C3 C4 103.46(9) ?
    C2 C3 C12 114.70(10)
                       ?
    C4 C3 C12 114.00(10)
                       ?
    N C4 C3 102.51(9) ?
    N C4 C13 112.90(10)
                      ?
    C3 C4 C13 113.50(10)
                       ?
    C1 C5 C6 113.10(10)
                      ?
    C5 C6 C7 120.30(10)
                      ?
    C5 C6 C11 121.30(10)
                       ?
    C7 C6 C11 118.50(10)
                       ?
    C6 C7 C8 121.00(10)
                      ?
    C7 C8 C9 119.90(10)
                      ?
    C8 C9 C10 119.90(10)
                       ?
    C9 C10 C11 120.40(10)
                        ?
    C6 C11 C10 120.30(10)
                        ?
    O2 C14 O3 125.30(10)
                       ?
    O2 C14 N 123.70(10)
                      ?
    O3 C14 N 110.90(10)
                      ?
    O3 C15 C16 101.66(9) ?
    O3 C15 C17 110.70(10)
                        ?
    O3 C15 C18 110.02(9) ?
    C16 C15 C17 110.80(10)
                         ?
    C16 C15 C18 110.70(10)
                         ?
    C17 C15 C18 112.40(10)
                         ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion
    _geom_torsion_publ_flag
    C15 O3 C14 O2 -17.1(2) ?
    C15 O3 C14 N 164.20(10)
                          ?
    C14 O3 C15 C16 -172.00(10)
                             ?
    C14 O3 C15 C17 70.10(10)
                           ?
    C14 O3 C15 C18 -54.70(10)
                            ?
    C4 N C1 C2 14.10(10)
                       ?
    C4 N C1 C5 -108.20(10)
                         ?
    C14 N C1 C2 -147.30(10)
                          ?
    C14 N C1 C5 90.40(10)
                        ?
    C1 N C4 C3 10.50(10)
                       ?
    C1 N C4 C13 133.00(10)
                         ?
    C14 N C4 C3 172.50(10)
                         ?
    C14 N C4 C13 -65.00(10)
                          ?
    C1 N C14 O2 166.00(10)
                         ?
    C1 N C14 O3 -15.3(2) ?
    C4 N C14 O2 6.0(12)
                       ?
    C4 N C14 O3 -175.30(10)
                          ?
    N C1 C2 O1 82.20(10)
                       ?
    N C1 C2 C3 -33.00(10)
                        ?
    C5 C1 C2 O1 -157.40(10)
                          ?
    C5 C1 C2 C3 87.50(10)
                        ?
    N C1 C5 C6 -172.80(10)
                         ?
    C2 C1 C5 C6 72.10(10)
                        ?
    O1 C2 C3 C4 -76.90(10)
                         ?
    O1 C2 C3 C12 47.80(10)
                         ?
    C1 C2 C3 C4 40.30(10)
                        ?
    C1 C2 C3 C12 165.10(10)
                          ?
    C2 C3 C4 N -30.90(10)
                        ?
    C2 C3 C4 C13 -153.10(10)
                           ?
    C12 C3 C4 N -156.20(10)
                          ?
    C12 C3 C4 C13 81.70(10)
                          ?
    C1 C5 C6 C7 63.20(10)
                        ?
    C1 C5 C6 C11 -117.90(10)
                           ?
    C5 C6 C7 C8 178.50(10)
                         ?
    C11 C6 C7 C8 -0.4(2) ?
    C5 C6 C11 C10 -177.80(10)
                            ?
    C7 C6 C11 C10 1.1(2) ?
    C6 C7 C8 C9 -0.7(2) ?
    C7 C8 C9 C10 1.1(2) ?
    C8 C9 C10 C11 -0.5(2) ?
    C9 C10 C11 C6 -0.6(2) ?
