#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/40/2014084.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_2014084
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         'C18 H21 N2 O + , Cl -'
_chemical_formula_sum            'C18 H21 Cl N2 O'
_chemical_formula_weight         316.82
_chemical_name_systematic
;
2-ammoniomethyl-1-benzyl-5-oxo-2-phenylpyrrolidine chloride
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                99.74(3)
_cell_angle_beta                 92.53(3)
_cell_angle_gamma                111.39(3)
_cell_formula_units_Z            2
_cell_length_a                   8.8302(18)
_cell_length_b                   10.077(2)
_cell_length_c                   10.094(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      17.8
_cell_measurement_theta_min      12.54
_cell_volume                     818.8(4)
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9597
_diffrn_reflns_theta_full        29.96
_diffrn_reflns_theta_max         29.96
_diffrn_reflns_theta_min         2.06
_diffrn_standards_decay_%        'no decay, variation < 1.0'
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sphere
_exptl_crystal_F_000             336
_exptl_crystal_size_rad          0.23
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.162
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0369
_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)+(0.056P)²+0.1106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1069
_reflns_number_gt                3895
_reflns_number_total             4767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tr1074.cif
_cod_data_source_block           II
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 'Triclinic' changed to 'triclinic'
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_cell_volume        818.7(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               2014084
_cod_database_fobs_code          2014084
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
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'
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
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 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_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_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
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 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
