##############################################################################
###                                                                        ###
###           Full Paper (Acta Crystallographica Section C)                ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section C. It conforms to the editorial and technical    #
# requirements of Notes for Authors for Section C, and has been peer         #
# reviewed under the auspices of the IUCr Commission on Journals.            #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# 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/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2003-11-13
_journal_date_accepted     2004-04-01
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2004
_journal_volume     60
_journal_issue      6
_journal_page_first     o390
_journal_page_last     o392
_journal_paper_category     FO
_publ_contact_author_name     'Dr Rafael Tamazyan'
_publ_contact_author_address
;
Molecule Structure Research Center
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
_publ_contact_author_email     rafael@msrc.am
_publ_contact_author_fax     '374 1 281 380'
_publ_contact_author_phone     '374 1 281 764'
_publ_section_title
;
1,2,5-Substituted derivatives of 2-phenylpyrrolidine
;
loop_
    _publ_author_name
    _publ_author_address
    'Tamazyan, Rafael'
;
Molecule Structure Research Center
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
    'Karapetyan, Harutyun'
;
Molecule Structure Research Center
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
    'Martirisyan, Ashot'
;
Institute of Fine Organic Chemistry
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
    'Martirosyan, Vahan'
;
Institute of Fine Organic Chemistry
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
    'Harutyunyan, Gohar'
;
Institute of Fine Organic Chemistry
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
    'Gasparyan, Sahak'
;
Institute of Fine Organic Chemistry
National Academy of Sciences RA
Azatutyan Avenue 26
375014 Yerevan
Republic of Armenia
;
data_I
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
1-tert-butoxycarbonyl-2-phenylpyrrolidine-2-carboxylic acid
;
_chemical_name_common     ?
_chemical_formula_moiety     'C16 H21 N O4'
_chemical_formula_sum     'C16 H21 N O4'
_chemical_formula_weight     291.34
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     Cc
_symmetry_space_group_name_Hall     'C-2yc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x, -y, z+1/2'
    'x+1/2, y+1/2, z'
    'x+1/2, -y+1/2, z+1/2'
_cell_length_a     19.309(4)
_cell_length_b     6.4210(13)
_cell_length_c     13.735(3)
_cell_angle_alpha     90.00
_cell_angle_beta     113.20(3)
_cell_angle_gamma     90.00
_cell_volume     1565.2(7)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     9.97
_cell_measurement_theta_max     17.2
_cell_measurement_temperature     293(2)
_exptl_crystal_description     prism
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.3
_exptl_crystal_size_mid     0.24
_exptl_crystal_size_min     0.18
_exptl_crystal_density_diffrn     1.236
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     624
_exptl_absorpt_coefficient_mu     0.089
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     'θ/2θ'
_diffrn_reflns_number     8331
_diffrn_reflns_av_R_equivalents     0.0356
_diffrn_reflns_av_sigmaI/netI     0.0302
_diffrn_reflns_theta_min     2.30
_diffrn_reflns_theta_max     29.98
_diffrn_reflns_theta_full     29.98
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -26
_diffrn_reflns_limit_h_max     26
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -19
_diffrn_reflns_limit_l_max     19
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     'no decay, variation < 1.0'
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    2 2 4
    -2 2 -4
    -2 -2 -4
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2273
_reflns_number_gt     1635
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0679
_refine_ls_R_factor_gt     0.0409
_refine_ls_wR_factor_gt     0.0873
_refine_ls_wR_factor_ref     0.0976
_refine_ls_goodness_of_fit_ref     1.037
_refine_ls_restrained_S_all     1.034
_refine_ls_number_reflns     2273
_refine_ls_number_parameters     220
_refine_ls_number_restraints     17
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w = 1/[σ²(Fo²)+(0.0494P)²+0.13P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.132
_refine_diff_density_min     -0.118
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_extinction_coef     0.0054(8)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Manual (Enraf-Nonius, 1988)'
_computing_cell_refinement     'CAD-4 Manual'
_computing_data_reduction     'HELENA (Spek, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL-NT (Bruker, 2000)'
_computing_publication_material     'SHELXTL-NT'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    C1 0.99477(11) 0.4888(3) 0.79329(15) 0.0397(4) Uani d . 1 . . C
    N2 0.94542(9) 0.3128(3) 0.78992(13) 0.0395(3) Uani d . 1 . . N
    C3 0.96748(13) 0.2043(3) 0.89149(16) 0.0492(5) Uani d . 1 . . C
    H3A 0.9792 0.0594 0.8848 0.059 Uiso calc R 1 . . H
    H3B 0.9276 0.2106 0.9176 0.059 Uiso calc R 1 . . H
    C4 1.03636(15) 0.3196(5) 0.96428(18) 0.0639(7) Uani d . 1 . . C
    H4A 1.0820 0.2493 0.9688 0.077 Uiso calc R 1 . . H
    H4B 1.0366 0.3308 1.0349 0.077 Uiso calc R 1 . . H
    C5 1.03030(14) 0.5324(4) 0.91435(17) 0.0543(5) Uani d . 1 . . C
    H5A 1.0796 0.5962 0.9350 0.065 Uiso calc R 1 . . H
    H5B 0.9983 0.6235 0.9349 0.065 Uiso calc R 1 . . H
    C6 0.88397(10) 0.2527(3) 0.70638(15) 0.0386(4) Uani d . 1 . . C
    O7 0.84372(7) 0.1085(2) 0.71039(12) 0.0500(4) Uani d . 1 . . O
    O8 0.87270(8) 0.3682(2) 0.62149(10) 0.0460(3) Uani d . 1 A . O
    C9 0.81211(12) 0.3243(4) 0.51839(18) 0.0525(6) Uani d D 1 . . C
    C10A 0.7327(3) 0.3062(17) 0.5103(6) 0.067(2) Uani d PD 0.432(8) A 1 C
    H10A 0.7187 0.4319 0.5359 0.101 Uiso calc PR 0.432(8) A 1 H
    H10B 0.7288 0.1904 0.5521 0.101 Uiso calc PR 0.432(8) A 1 H
    H10C 0.6995 0.2847 0.4376 0.101 Uiso calc PR 0.432(8) A 1 H
    C11A 0.8403(4) 0.1299(9) 0.4803(5) 0.0547(18) Uani d PDU 0.432(8) A 1 C
    H11A 0.8842 0.1648 0.4670 0.082 Uiso calc PR 0.432(8) A 1 H
    H11B 0.8015 0.0794 0.4162 0.082 Uiso calc PR 0.432(8) A 1 H
    H11C 0.8530 0.0239 0.5338 0.082 Uiso calc PR 0.432(8) A 1 H
    C12A 0.8124(7) 0.4982(13) 0.4444(8) 0.075(3) Uani d PDU 0.432(8) A 1 C
    H12A 0.7963 0.6252 0.4658 0.113 Uiso calc PR 0.432(8) A 1 H
    H12B 0.7787 0.4641 0.3734 0.113 Uiso calc PR 0.432(8) A 1 H
    H12C 0.8625 0.5158 0.4469 0.113 Uiso calc PR 0.432(8) A 1 H
    C10B 0.7426(3) 0.379(2) 0.5381(7) 0.143(5) Uani d PD 0.568(8) A 2 C
    H10D 0.7472 0.5178 0.5655 0.215 Uiso calc PR 0.568(8) A 2 H
    H10E 0.7374 0.2829 0.5885 0.215 Uiso calc PR 0.568(8) A 2 H
    H10F 0.6990 0.3697 0.4728 0.215 Uiso calc PR 0.568(8) A 2 H
    C11B 0.8134(7) 0.0988(11) 0.4852(8) 0.143(5) Uani d PDU 0.568(8) A 2 C
    H11D 0.7722 0.0246 0.4917 0.215 Uiso calc PR 0.568(8) A 2 H
    H11E 0.8601 0.0354 0.5301 0.215 Uiso calc PR 0.568(8) A 2 H
    H11F 0.8086 0.0940 0.4130 0.215 Uiso calc PR 0.568(8) A 2 H
    C12B 0.8271(5) 0.4893(13) 0.4505(5) 0.068(2) Uani d PDU 0.568(8) A 2 C
    H12D 0.8125 0.6230 0.4673 0.102 Uiso calc PR 0.568(8) A 2 H
    H12E 0.7985 0.4586 0.3771 0.102 Uiso calc PR 0.568(8) A 2 H
    H12F 0.8798 0.4909 0.4641 0.102 Uiso calc PR 0.568(8) A 2 H
    C13 0.94951(11) 0.6821(3) 0.73730(16) 0.0431(5) Uani d . 1 . . C
    O14 0.89222(9) 0.7196(2) 0.76473(13) 0.0559(4) Uani d . 1 . . O
    H14 0.8753 0.8361 0.7443 0.084 Uiso calc R 1 . . H
    O15 0.96694(9) 0.7932(3) 0.68045(14) 0.0581(4) Uani d . 1 . . O
    C16 1.05564(11) 0.4345(3) 0.75280(14) 0.0424(4) Uani d . 1 . . C
    C17 1.11241(12) 0.5778(4) 0.76433(17) 0.0540(6) Uani d . 1 . . C
    H17 1.1120 0.7071 0.7946 0.065 Uiso calc R 1 . . H
    C18 1.16967(13) 0.5291(5) 0.7310(2) 0.0654(7) Uani d . 1 . . C
    H18 1.2072 0.6260 0.7386 0.079 Uiso calc R 1 . . H
    C19 1.17091(14) 0.3391(6) 0.6871(2) 0.0710(8) Uani d . 1 . . C
    H19 1.2095 0.3066 0.6652 0.085 Uiso calc R 1 . . H
    C21 1.05759(13) 0.2436(4) 0.70779(17) 0.0511(5) Uani d . 1 . . C
    H21 1.0201 0.1459 0.6992 0.061 Uiso calc R 1 . . H
    C20 1.11565(15) 0.1967(5) 0.6751(2) 0.0660(7) Uani d . 1 . . C
    H20 1.1167 0.0676 0.6450 0.079 Uiso calc R 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
  16.4635 (0.0154) x - 3.1265 (0.0071) y - 7.0063 (0.0152) z = 9.1171
(0.0205)
 *    0.1741 (0.0014)  C1
 *   -0.0645 (0.0014)  N2
 *   -0.0737 (0.0015)  C3
 *    0.1897 (0.0017)  C4
 *   -0.2256 (0.0016)  C5
 Rms deviation of fitted atoms =   0.1592
  3.9275 (0.0177) x - 2.3844 (0.0059) y + 10.3363 (0.0099) z = 10.8903
(0.0168)
 Angle to previous plane (with approximate esd) = 79.48 ( 0.09 )
 *    0.0008 (0.0014)  C16
 *    0.0012 (0.0015)  C17
 *   -0.0024 (0.0017)  C18
 *    0.0015 (0.0018)  C19
 *    0.0005 (0.0018)  C20
 *   -0.0016 (0.0016)  C21
 Rms deviation of fitted atoms =   0.0015
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N2 . 1.467(2) n
    C1 C16 . 1.526(3) n
    C1 C13 . 1.538(3) n
    C1 C5 . 1.554(3) n
    N2 C6 . 1.342(2) n
    N2 C3 . 1.465(3) n
    C3 C4 . 1.507(3) n
    C3 H3A . 0.9700 n
    C3 H3B . 0.9700 n
    C4 C5 . 1.513(4) n
    C4 H4A . 0.9700 n
    C4 H4B . 0.9700 n
    C5 H5A . 0.9700 n
    C5 H5B . 0.9700 n
    C6 O7 . 1.224(2) n
    C6 O8 . 1.326(2) n
    O8 C9 . 1.466(3) n
    C9 C10A . 1.498(6) n
    C9 C10B . 1.511(7) n
    C9 C12A . 1.512(7) n
    C9 C12B . 1.512(6) n
    C9 C11B . 1.521(7) n
    C9 C11A . 1.534(6) n
    C10A H10A . 0.9600 n
    C10A H10B . 0.9600 n
    C10A H10C . 0.9600 n
    C11A H11A . 0.9600 n
    C11A H11B . 0.9600 n
    C11A H11C . 0.9600 n
    C12A H12A . 0.9600 n
    C12A H12B . 0.9600 n
    C12A H12C . 0.9600 n
    C10B H10D . 0.9600 n
    C10B H10E . 0.9600 n
    C10B H10F . 0.9600 n
    C11B H11D . 0.9600 n
    C11B H11E . 0.9600 n
    C11B H11F . 0.9600 n
    C12B H12D . 0.9600 n
    C12B H12E . 0.9600 n
    C12B H12F . 0.9600 n
    C13 O15 . 1.200(3) n
    C13 O14 . 1.324(3) n
    O14 H14 . 0.8200 n
    C16 C21 . 1.380(3) n
    C16 C17 . 1.392(3) n
    C17 C18 . 1.389(4) n
    C17 H17 . 0.9300 n
    C18 C19 . 1.365(5) n
    C18 H18 . 0.9300 n
    C19 C20 . 1.365(4) n
    C19 H19 . 0.9300 n
    C21 C20 . 1.395(4) n
    C21 H21 . 0.9300 n
    C20 H20 . 0.9300 n
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 C1 C16 . . 113.36(16) n
    N2 C1 C13 . . 111.82(16) n
    C16 C1 C13 . . 111.71(16) n
    N2 C1 C5 . . 100.37(16) n
    C16 C1 C5 . . 110.64(17) n
    C13 C1 C5 . . 108.29(17) n
    C6 N2 C3 . . 120.31(17) n
    C6 N2 C1 . . 126.38(16) n
    C3 N2 C1 . . 113.27(16) n
    N2 C3 C4 . . 104.32(18) n
    N2 C3 H3A . . 110.9 n
    C4 C3 H3A . . 110.9 n
    N2 C3 H3B . . 110.9 n
    C4 C3 H3B . . 110.9 n
    H3A C3 H3B . . 108.9 n
    C3 C4 C5 . . 104.66(18) n
    C3 C4 H4A . . 110.8 n
    C5 C4 H4A . . 110.8 n
    C3 C4 H4B . . 110.8 n
    C5 C4 H4B . . 110.8 n
    H4A C4 H4B . . 108.9 n
    C4 C5 C1 . . 104.18(18) n
    C4 C5 H5A . . 110.9 n
    C1 C5 H5A . . 110.9 n
    C4 C5 H5B . . 110.9 n
    C1 C5 H5B . . 110.9 n
    H5A C5 H5B . . 108.9 n
    O7 C6 O8 . . 125.15(17) n
    O7 C6 N2 . . 122.85(18) n
    O8 C6 N2 . . 111.99(16) n
    C6 O8 C9 . . 122.30(16) n
    O8 C9 C10A . . 119.4(4) n
    O8 C9 C10B . . 102.1(4) n
    O8 C9 C12A . . 107.1(4) n
    C10A C9 C12A . . 106.4(6) n
    O8 C9 C12B . . 100.8(3) n
    C10B C9 C12B . . 110.4(6) n
    O8 C9 C11B . . 111.8(4) n
    C10B C9 C11B . . 113.2(7) n
    C12B C9 C11B . . 116.9(6) n
    O8 C9 C11A . . 103.3(3) n
    C10A C9 C11A . . 113.7(5) n
    C12A C9 C11A . . 106.0(6) n
    C9 C10A H10A . . 109.5 n
    C9 C10A H10B . . 109.5 n
    H10A C10A H10B . . 109.5 n
    C9 C10A H10C . . 109.5 n
    H10A C10A H10C . . 109.5 n
    H10B C10A H10C . . 109.5 n
    C9 C11A H11A . . 109.5 n
    C9 C11A H11B . . 109.5 n
    H11A C11A H11B . . 109.5 n
    C9 C11A H11C . . 109.5 n
    H11A C11A H11C . . 109.5 n
    H11B C11A H11C . . 109.5 n
    C9 C12A H12A . . 109.5 n
    C9 C12A H12B . . 109.5 n
    H12A C12A H12B . . 109.5 n
    C9 C12A H12C . . 109.5 n
    H12A C12A H12C . . 109.5 n
    H12B C12A H12C . . 109.5 n
    C9 C10B H10D . . 109.5 n
    C9 C10B H10E . . 109.5 n
    H10D C10B H10E . . 109.5 n
    C9 C10B H10F . . 109.5 n
    H10D C10B H10F . . 109.5 n
    H10E C10B H10F . . 109.5 n
    C9 C11B H11D . . 109.5 n
    C9 C11B H11E . . 109.5 n
    H11D C11B H11E . . 109.5 n
    C9 C11B H11F . . 109.5 n
    H11D C11B H11F . . 109.5 n
    H11E C11B H11F . . 109.5 n
    C9 C12B H12D . . 109.5 n
    C9 C12B H12E . . 109.5 n
    H12D C12B H12E . . 109.5 n
    C9 C12B H12F . . 109.5 n
    H12D C12B H12F . . 109.5 n
    H12E C12B H12F . . 109.5 n
    O15 C13 O14 . . 123.86(19) n
    O15 C13 C1 . . 123.74(19) n
    O14 C13 C1 . . 112.24(17) n
    C13 O14 H14 . . 109.5 n
    C21 C16 C17 . . 118.6(2) n
    C21 C16 C1 . . 121.82(18) n
    C17 C16 C1 . . 119.53(19) n
    C18 C17 C16 . . 120.5(3) n
    C18 C17 H17 . . 119.8 n
    C16 C17 H17 . . 119.8 n
    C19 C18 C17 . . 120.1(2) n
    C19 C18 H18 . . 119.9 n
    C17 C18 H18 . . 119.9 n
    C18 C19 C20 . . 120.2(2) n
    C18 C19 H19 . . 119.9 n
    C20 C19 H19 . . 119.9 n
    C16 C21 C20 . . 120.2(2) n
    C16 C21 H21 . . 119.9 n
    C20 C21 H21 . . 119.9 n
    C19 C20 C21 . . 120.4(3) n
    C19 C20 H20 . . 119.8 n
    C21 C20 H20 . . 119.8 n
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C16 C1 N2 C6 . . . . -85.0(2) n
    C13 C1 N2 C6 . . . . 42.3(3) n
    C5 C1 N2 C6 . . . . 156.97(19) n
    C16 C1 N2 C3 . . . . 97.2(2) n
    C13 C1 N2 C3 . . . . -135.47(17) n
    C5 C1 N2 C3 . . . . -20.8(2) n
    C6 N2 C3 C4 . . . . -178.40(19) n
    C1 N2 C3 C4 . . . . -0.4(2) n
    N2 C3 C4 C5 . . . . 22.5(3) n
    C3 C4 C5 C1 . . . . -35.6(3) n
    N2 C1 C5 C4 . . . . 33.8(2) n
    C16 C1 C5 C4 . . . . -86.2(2) n
    C13 C1 C5 C4 . . . . 151.10(19) n
    C3 N2 C6 O7 . . . . 0.4(3) n
    C1 N2 C6 O7 . . . . -177.22(19) n
    C3 N2 C6 O8 . . . . 179.98(18) n
    C1 N2 C6 O8 . . . . 2.3(3) n
    O7 C6 O8 C9 . . . . -4.7(3) n
    N2 C6 O8 C9 . . . . 175.81(18) n
    C6 O8 C9 C10A . . . . 54.1(6) n
    C6 O8 C9 C10B . . . . 69.4(6) n
    C6 O8 C9 C12A . . . . 175.0(5) n
    C6 O8 C9 C12B . . . . -176.8(4) n
    C6 O8 C9 C11B . . . . -51.9(7) n
    C6 O8 C9 C11A . . . . -73.3(4) n
    N2 C1 C13 O15 . . . . -138.3(2) n
    C16 C1 C13 O15 . . . . -10.1(3) n
    C5 C1 C13 O15 . . . . 112.0(2) n
    N2 C1 C13 O14 . . . . 46.0(2) n
    C16 C1 C13 O14 . . . . 174.26(15) n
    C5 C1 C13 O14 . . . . -63.7(2) n
    N2 C1 C16 C21 . . . . 6.3(3) n
    C13 C1 C16 C21 . . . . -121.1(2) n
    C5 C1 C16 C21 . . . . 118.1(2) n
    N2 C1 C16 C17 . . . . -171.58(16) n
    C13 C1 C16 C17 . . . . 61.0(2) n
    C5 C1 C16 C17 . . . . -59.7(2) n
    C21 C16 C17 C18 . . . . 0.1(3) n
    C1 C16 C17 C18 . . . . 178.0(2) n
    C16 C17 C18 C19 . . . . -0.4(3) n
    C17 C18 C19 C20 . . . . 0.4(4) n
    C17 C16 C21 C20 . . . . 0.2(3) n
    C1 C16 C21 C20 . . . . -177.7(2) n
    C18 C19 C20 C21 . . . . -0.1(4) n
    C16 C21 C20 C19 . . . . -0.2(4) n
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O14 H14 O7 1_555 1_555 1_565 0.82 1.85 2.668(2) 175 y
data_II
_audit_creation_method     SHELXL97
_chemical_name_systematic
;
2-ammoniomethyl-1-benzyl-5-oxo-2-phenylpyrrolidine chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H21 N2 O + , Cl -'
_chemical_formula_sum     'C18 H21 Cl N2 O'
_chemical_formula_weight     316.82
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     P-1
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.8302(18)
_cell_length_b     10.077(2)
_cell_length_c     10.094(2)
_cell_angle_alpha     99.74(3)
_cell_angle_beta     92.53(3)
_cell_angle_gamma     111.39(3)
_cell_volume     818.7(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     12.54
_cell_measurement_theta_max     17.8
_cell_measurement_temperature     293(2)
_exptl_crystal_description     sphere
_exptl_crystal_colour     colourless
_exptl_crystal_size_rad     0.23
_exptl_crystal_density_diffrn     1.285
_exptl_crystal_density_meas     'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     336
_exptl_absorpt_coefficient_mu     0.237
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf-Nonius CAD-4'
_diffrn_measurement_method     'θ/2θ'
_diffrn_reflns_number     9597
_diffrn_reflns_av_R_equivalents     0.0166
_diffrn_reflns_av_sigmaI/netI     0.0207
_diffrn_reflns_theta_min     2.06
_diffrn_reflns_theta_max     29.96
_diffrn_reflns_theta_full     29.96
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -12
_diffrn_reflns_limit_h_max     12
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -14
_diffrn_reflns_limit_l_max     14
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     'no decay, variation < 1.0'
loop_
    _diffrn_standard_refln_index_h
    _diffrn_standard_refln_index_k
    _diffrn_standard_refln_index_l
    2 -5 0
    -3 5 6
    2 6 -1
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     4767
_reflns_number_gt     3895
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0471
_refine_ls_R_factor_gt     0.0369
_refine_ls_wR_factor_gt     0.1007
_refine_ls_wR_factor_ref     0.1069
_refine_ls_goodness_of_fit_ref     1.030
_refine_ls_restrained_S_all     1.030
_refine_ls_number_reflns     4767
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refall
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
        'calc w = 1/[σ²(Fo²)+(0.056P)²+0.1106P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.258
_refine_diff_density_min     -0.162
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0061 0.0033
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.1484 0.1585
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'CAD-4 Manual (Enraf-Nonius, 1988)'
_computing_cell_refinement     'CAD-4 Manual'
_computing_data_reduction     'HELENA (Spek, 1997)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'SHELXTL-NT (Bruker, 2000)'
_computing_publication_material     'SHELXTL-NT'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Cl1 0.14123(4) 0.85572(4) 0.03042(3) 0.04903(10) Uani d . 1 . . Cl
    C1 0.69819(13) 0.73955(11) 0.24450(10) 0.0330(2) Uani d . 1 . . C
    N2 0.73860(10) 0.81544(9) 0.38775(8) 0.03181(17) Uani d . 1 . . N
    C3 0.87058(13) 0.80799(12) 0.45323(11) 0.0362(2) Uani d . 1 . . C
    C4 0.93727(18) 0.71681(18) 0.35789(16) 0.0549(3) Uani d . 1 . . C
    H4B 1.048(3) 0.780(3) 0.347(2) 0.100(7) Uiso d . 1 . . H
    H4A 0.945(2) 0.645(2) 0.397(2) 0.084(6) Uiso d . 1 . . H
    C5 0.82233(15) 0.66214(13) 0.22876(12) 0.0414(2) Uani d . 1 . . C
    H5B 0.7636(18) 0.5563(18) 0.2169(16) 0.053(4) Uiso d . 1 . . H
    H5A 0.883(2) 0.6862(18) 0.1523(17) 0.059(4) Uiso d . 1 . . H
    C6 0.65558(15) 0.90841(12) 0.44887(12) 0.0382(2) Uani d . 1 . . C
    H6B 0.736(2) 0.9997(18) 0.4965(17) 0.056(4) Uiso d . 1 . . H
    H6A 0.6008(16) 0.9299(15) 0.3783(14) 0.040(3) Uiso d . 1 . . H
    C7 0.53920(14) 0.84941(12) 0.54986(11) 0.0374(2) Uani d . 1 . . C
    C8 0.37941(15) 0.75191(14) 0.50758(13) 0.0450(3) Uani d . 1 . . C
    H8 0.342(2) 0.7135(18) 0.4074(18) 0.061(4) Uiso d . 1 . . H
    C9 0.27242(18) 0.70622(16) 0.60215(16) 0.0539(3) Uani d . 1 . . C
    H9 0.170(2) 0.640(2) 0.5736(19) 0.070(5) Uiso d . 1 . . H
    C10 0.3219(2) 0.75825(18) 0.73827(16) 0.0577(4) Uani d . 1 . . C
    H10 0.249(2) 0.7268(19) 0.8051(19) 0.067(5) Uiso d . 1 . . H
    C11 0.4789(2) 0.85651(19) 0.78105(14) 0.0576(4) Uani d . 1 . . C
    H11 0.515(2) 0.895(2) 0.875(2) 0.076(5) Uiso d . 1 . . H
    C12 0.58783(17) 0.90176(16) 0.68722(12) 0.0479(3) Uani d . 1 . . C
    H12 0.698(2) 0.9713(17) 0.7182(17) 0.054(4) Uiso d . 1 . . H
    C13 0.72724(15) 0.85107(13) 0.15286(11) 0.0385(2) Uani d . 1 . . C
    H13B 0.7096(18) 0.8047(17) 0.0624(17) 0.051(4) Uiso d . 1 . . H
    H13A 0.6545(17) 0.8999(15) 0.1607(14) 0.042(3) Uiso d . 1 . . H
    N14 0.89545(13) 0.96403(11) 0.17746(10) 0.0411(2) Uani d . 1 . . N
    H14C 0.972(2) 0.9311(19) 0.1478(17) 0.060(5) Uiso d . 1 . . H
    H14B 0.895(2) 1.0285(19) 0.1280(18) 0.061(5) Uiso d . 1 . . H
    H14A 0.9261(18) 1.0069(16) 0.2624(16) 0.047(4) Uiso d . 1 . . H
    O15 0.92545(11) 0.86771(10) 0.57096(8) 0.0477(2) Uani d . 1 . . O
    C16 0.52005(14) 0.63198(12) 0.22045(11) 0.0380(2) Uani d . 1 . . C
    C17 0.39834(17) 0.64927(16) 0.14166(14) 0.0529(3) Uani d . 1 . . C
    H17 0.422(2) 0.7283(19) 0.0899(17) 0.060(4) Uiso d . 1 . . H
    C18 0.23676(19) 0.5517(2) 0.12922(18) 0.0691(4) Uani d . 1 . . C
    H18 0.158(2) 0.570(2) 0.076(2) 0.081(6) Uiso d . 1 . . H
    C19 0.1960(2) 0.43702(18) 0.1948(2) 0.0722(5) Uani d . 1 . . C
    H19 0.091(3) 0.371(2) 0.186(2) 0.091(6) Uiso d . 1 . . H
    C20 0.3150(2) 0.41861(16) 0.2737(2) 0.0674(4) Uani d . 1 . . C
    H20 0.290(3) 0.342(2) 0.320(2) 0.088(6) Uiso d . 1 . . H
    C21 0.47608(17) 0.51574(14) 0.28732(16) 0.0512(3) Uani d . 1 . . C
    H21 0.556(2) 0.5037(18) 0.3447(17) 0.057(4) Uiso d . 1 . . H
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)
 - 3.9131 (0.0057) x + 5.5447 (0.0066) y + 7.1991 (0.0063) z = 3.0604
(0.0034)
 *   -0.0042 (0.0009)  C16
 *    0.0006 (0.0011)  C17
 *    0.0025 (0.0012)  C18
 *   -0.0020 (0.0013)  C19
 *   -0.0016 (0.0012)  C20
 *    0.0047 (0.0011)  C21
 Rms deviation of fitted atoms =   0.0030
 - 5.5031 (0.0049) x + 9.6185 (0.0053) y - 1.6835 (0.0057) z = 4.2826
(0.0051)
 Angle to previous plane (with approximate esd) = 55.20 ( 0.06 )
 *   -0.0055 (0.0008)  C7
 *    0.0072 (0.0009)  C8
 *   -0.0027 (0.0010)  C9
 *   -0.0036 (0.0010)  C10
 *    0.0053 (0.0010)  C11
 *   -0.0008 (0.0009)  C12
 Rms deviation of fitted atoms =   0.0047
  3.0322 (0.0060) x + 7.0377 (0.0061) y - 5.0482 (0.0054) z = 6.0450
(0.0045)
 Angle to previous plane (with approximate esd) = 60.70 ( 0.05 )
 *    0.0424 (0.0007)  C1
 *   -0.0240 (0.0006)  N2
 *   -0.0069 (0.0008)  C3
 *    0.0349 (0.0009)  C4
 *   -0.0465 (0.0008)  C5
 Rms deviation of fitted atoms =   0.0341
 - 3.9131 (0.0057) x + 5.5447 (0.0066) y + 7.1991 (0.0063) z = 3.0604
(0.0034)
 Angle to previous plane (with approximate esd) = 88.09 ( 0.06 )
 *   -0.0042 (0.0009)  C16
 *    0.0006 (0.0011)  C17
 *    0.0025 (0.0012)  C18
 *   -0.0020 (0.0013)  C19
 *   -0.0016 (0.0012)  C20
 *    0.0047 (0.0011)  C21
 Rms deviation of fitted atoms =   0.0030
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 N2 . 1.4779(14) n
    C1 C16 . 1.5302(16) n
    C1 C13 . 1.5319(15) n
    C1 C5 . 1.5596(16) n
    N2 C3 . 1.3466(14) n
    N2 C6 . 1.4632(14) n
    C3 O15 . 1.2262(14) n
    C3 C4 . 1.5042(18) n
    C4 C5 . 1.505(2) n
    C4 H4B . 0.98(2) n
    C4 H4A . 0.90(2) n
    C5 H5B . 0.984(16) n
    C5 H5A . 0.973(17) n
    C6 C7 . 1.5168(16) n
    C6 H6B . 0.962(17) n
    C6 H6A . 0.941(14) n
    C7 C12 . 1.3855(17) n
    C7 C8 . 1.3899(18) n
    C8 C9 . 1.3881(19) n
    C8 H8 . 1.013(18) n
    C9 C10 . 1.375(2) n
    C9 H9 . 0.901(18) n
    C10 C11 . 1.375(2) n
    C10 H10 . 0.965(19) n
    C11 C12 . 1.392(2) n
    C11 H11 . 0.95(2) n
    C12 H12 . 0.969(16) n
    C13 N14 . 1.4839(16) n
    C13 H13B . 0.931(16) n
    C13 H13A . 0.939(15) n
    N14 H14C . 0.896(18) n
    N14 H14B . 0.885(18) n
    N14 H14A . 0.874(16) n
    C16 C17 . 1.3877(18) n
    C16 C21 . 1.3918(17) n
    C17 C18 . 1.392(2) n
    C17 H17 . 0.990(17) n
    C18 C19 . 1.371(3) n
    C18 H18 . 0.95(2) n
    C19 C20 . 1.376(3) n
    C19 H19 . 0.92(2) n
    C20 C21 . 1.386(2) n
    C20 H20 . 0.93(2) n
    C21 H21 . 0.950(16) n
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    N2 C1 C16 . . 109.65(9) n
    N2 C1 C13 . . 109.65(9) n
    C16 C1 C13 . . 110.89(9) n
    N2 C1 C5 . . 102.41(9) n
    C16 C1 C5 . . 112.54(9) n
    C13 C1 C5 . . 111.35(9) n
    C3 N2 C6 . . 121.94(10) n
    C3 N2 C1 . . 115.18(9) n
    C6 N2 C1 . . 122.37(9) n
    O15 C3 N2 . . 124.49(11) n
    O15 C3 C4 . . 126.83(11) n
    N2 C3 C4 . . 108.68(10) n
    C3 C4 C5 . . 106.41(10) n
    C3 C4 H4B . . 106.9(14) n
    C5 C4 H4B . . 113.5(14) n
    C3 C4 H4A . . 108.8(14) n
    C5 C4 H4A . . 113.3(14) n
    H4B C4 H4A . . 107.7(19) n
    C4 C5 C1 . . 106.72(10) n
    C4 C5 H5B . . 109.3(9) n
    C1 C5 H5B . . 109.8(9) n
    C4 C5 H5A . . 110.2(10) n
    C1 C5 H5A . . 110.0(10) n
    H5B C5 H5A . . 110.7(13) n
    N2 C6 C7 . . 116.17(9) n
    N2 C6 H6B . . 109.2(10) n
    C7 C6 H6B . . 106.3(10) n
    N2 C6 H6A . . 107.8(8) n
    C7 C6 H6A . . 110.5(8) n
    H6B C6 H6A . . 106.4(13) n
    C12 C7 C8 . . 118.79(12) n
    C12 C7 C6 . . 119.70(11) n
    C8 C7 C6 . . 121.31(11) n
    C9 C8 C7 . . 120.17(13) n
    C9 C8 H8 . . 120.1(10) n
    C7 C8 H8 . . 119.7(10) n
    C10 C9 C8 . . 120.65(14) n
    C10 C9 H9 . . 120.0(12) n
    C8 C9 H9 . . 119.3(12) n
    C9 C10 C11 . . 119.62(13) n
    C9 C10 H10 . . 121.5(11) n
    C11 C10 H10 . . 118.9(11) n
    C10 C11 C12 . . 120.23(14) n
    C10 C11 H11 . . 120.7(12) n
    C12 C11 H11 . . 119.0(12) n
    C7 C12 C11 . . 120.53(14) n
    C7 C12 H12 . . 119.8(10) n
    C11 C12 H12 . . 119.7(10) n
    N14 C13 C1 . . 113.43(10) n
    N14 C13 H13B . . 107.5(9) n
    C1 C13 H13B . . 110.2(10) n
    N14 C13 H13A . . 107.0(9) n
    C1 C13 H13A . . 113.2(9) n
    H13B C13 H13A . . 105.0(13) n
    C13 N14 H14C . . 113.7(11) n
    C13 N14 H14B . . 105.8(11) n
    H14C N14 H14B . . 105.5(15) n
    C13 N14 H14A . . 113.5(10) n
    H14C N14 H14A . . 108.1(14) n
    H14B N14 H14A . . 109.9(14) n
    C17 C16 C21 . . 118.35(12) n
    C17 C16 C1 . . 123.25(11) n
    C21 C16 C1 . . 118.29(11) n
    C16 C17 C18 . . 120.59(15) n
    C16 C17 H17 . . 122.2(10) n
    C18 C17 H17 . . 117.2(10) n
    C19 C18 C17 . . 120.24(16) n
    C19 C18 H18 . . 122.5(12) n
    C17 C18 H18 . . 117.2(12) n
    C18 C19 C20 . . 119.92(15) n
    C18 C19 H19 . . 121.2(14) n
    C20 C19 H19 . . 118.9(14) n
    C19 C20 C21 . . 120.21(16) n
    C19 C20 H20 . . 121.6(13) n
    C21 C20 H20 . . 118.2(13) n
    C20 C21 C16 . . 120.69(15) n
    C20 C21 H21 . . 119.3(10) n
    C16 C21 H21 . . 120.0(10) n
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C16 C1 N2 C3 . . . . 125.64(9) n
    C13 C1 N2 C3 . . . . -112.39(10) n
    C5 C1 N2 C3 . . . . 5.94(11) n
    C16 C1 N2 C6 . . . . -62.39(12) n
    C13 C1 N2 C6 . . . . 59.58(12) n
    C5 C1 N2 C6 . . . . 177.91(9) n
    C6 N2 C3 O15 . . . . 5.74(16) n
    C1 N2 C3 O15 . . . . 177.74(10) n
    C6 N2 C3 C4 . . . . -173.77(11) n
    C1 N2 C3 C4 . . . . -1.76(13) n
    O15 C3 C4 C5 . . . . 177.04(11) n
    N2 C3 C4 C5 . . . . -3.47(15) n
    C3 C4 C5 C1 . . . . 6.93(15) n
    N2 C1 C5 C4 . . . . -7.59(12) n
    C16 C1 C5 C4 . . . . -125.25(12) n
    C13 C1 C5 C4 . . . . 109.52(12) n
    C3 N2 C6 C7 . . . . -79.67(13) n
    C1 N2 C6 C7 . . . . 108.90(12) n
    N2 C6 C7 C12 . . . . 102.59(13) n
    N2 C6 C7 C8 . . . . -82.58(14) n
    C12 C7 C8 C9 . . . . -1.29(18) n
    C6 C7 C8 C9 . . . . -176.16(11) n
    C7 C8 C9 C10 . . . . 1.0(2) n
    C8 C9 C10 C11 . . . . 0.0(2) n
    C9 C10 C11 C12 . . . . -0.8(2) n
    C8 C7 C12 C11 . . . . 0.53(18) n
    C6 C7 C12 C11 . . . . 175.49(12) n
    C10 C11 C12 C7 . . . . 0.5(2) n
    N2 C1 C13 N14 . . . . 55.21(13) n
    C16 C1 C13 N14 . . . . 176.45(9) n
    C5 C1 C13 N14 . . . . -57.41(13) n
    N2 C1 C16 C17 . . . . 111.94(13) n
    C13 C1 C16 C17 . . . . -9.29(15) n
    C5 C1 C16 C17 . . . . -134.77(12) n
    N2 C1 C16 C21 . . . . -64.16(13) n
    C13 C1 C16 C21 . . . . 174.61(11) n
    C5 C1 C16 C21 . . . . 49.13(14) n
    C21 C16 C17 C18 . . . . -0.6(2) n
    C1 C16 C17 C18 . . . . -176.65(13) n
    C16 C17 C18 C19 . . . . -0.1(3) n
    C17 C18 C19 C20 . . . . 0.3(3) n
    C18 C19 C20 C21 . . . . 0.1(3) n
    C19 C20 C21 C16 . . . . -0.7(2) n
    C17 C16 C21 C20 . . . . 1.0(2) n
    C1 C16 C21 C20 . . . . 177.24(13) n
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    N14 H14A O15 1_555 1_555 2_776 0.87(2) 2.01(2) 2.839(2) 159.0(10)
                                                                   y
    N14 H14B Cl1 1_555 1_555 2_675 0.88(2) 2.21(2) 3.0770(10)
                                                            167.0(10)
                                                                   y
    N14 H14C Cl1 1_555 1_555 1_655 0.90(2) 2.21(2) 3.0930(10)
                                                            167.0(10)
                                                                   y
