#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/40/2014083.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2014083
loop_
_publ_author_name
'Tamazyan, Rafael'
'Karapetyan, Harutyun'
'Martirisyan, Ashot'
'Martirosyan, Vahan'
'Harutyunyan, Gohar'
'Gasparyan, Sahak'
_publ_section_title
;
 1,2,5-Substituted derivatives of 2-phenylpyrrolidine
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o390
_journal_page_last               o392
_journal_paper_doi               10.1107/S0108270104007930
_journal_volume                  60
_journal_year                    2004
_chemical_formula_moiety         'C16 H21 N O4'
_chemical_formula_sum            'C16 H21 N O4'
_chemical_formula_weight         291.34
_chemical_name_systematic
;
1-tert-butoxycarbonyl-2-phenylpyrrolidine-2-carboxylic acid
;
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 113.20(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.309(4)
_cell_length_b                   6.4210(13)
_cell_length_c                   13.735(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.2
_cell_measurement_theta_min      9.97
_cell_volume                     1565.2(7)
_computing_cell_refinement       'CAD-4 Manual'
_computing_data_collection       'CAD-4 Manual (Enraf-Nonius, 1988)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'SHELXTL-NT (Bruker, 2000)'
_computing_publication_material  SHELXTL-NT
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8331
_diffrn_reflns_theta_full        29.98
_diffrn_reflns_theta_max         29.98
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        'no decay, variation < 1.0'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.118
_refine_ls_extinction_coef       0.0054(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2273
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0494P)²+0.13P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0976
_reflns_number_gt                1635
_reflns_number_total             2273
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tr1074.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_Hall     C-2yc
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2014083
_cod_database_fobs_code          2014083
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'
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
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'
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
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
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_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_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
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
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
