#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/78/2217848.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_2217848
loop_
_publ_author_name
'Dean, Pamela M.'
'Pringle, Jennifer M.'
'MacFarlane, Douglas R.'
_publ_section_title
;
 1-Methyl-1-propylpyrrolidinium chloride
;
_journal_coeditor_code           ZL2101
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o637
_journal_paper_doi               10.1107/S1600536808005229
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C8 H18 N +, Cl -'
_chemical_formula_moiety         'C8 H18 N +, Cl -'
_chemical_formula_sum            'C8 H18 Cl N'
_chemical_formula_weight         163.68
_chemical_melting_point          323.5
_chemical_name_common            '[C3mpyr][Cl]'
_chemical_name_systematic
;
1-Methyl-1-propylpyrrolidinium chloride
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   14.5863(5)
_cell_length_b                   13.2196(4)
_cell_length_c                   9.9779(3)
_cell_measurement_reflns_used    4825
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.79
_cell_volume                     1923.99(11)
_computing_cell_refinement       'APEX2 (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'APEX2 (Bruker, 2005)'
_computing_molecular_graphics    'POV-RAY (Persistence of Vision, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker X8 APEX KappaCCD'
_diffrn_measurement_method       '0.5° frames in φ and ω'
_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  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11550
_diffrn_reflns_theta_full        26.44
_diffrn_reflns_theta_max         26.44
_diffrn_reflns_theta_min         2.08
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.333
_exptl_absorpt_correction_T_max  0.9067
_exptl_absorpt_correction_T_min  0.9067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.130
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.197
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0361P)²+0.834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0794
_reflns_number_gt                1800
_reflns_number_total             1982
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2101.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 'Orthorhombic' changed to
'orthorhombic' 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 
;
_cod_database_code               2217848
_cod_database_fobs_code          2217848
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'
loop_
_atom_site_type_symbol
_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
Cl Cl1 0.36024(2) 0.82436(2) 0.05218(3) 0.02423(12) Uani d . 1
N N1 0.32912(7) 0.86923(8) 0.43497(10) 0.0179(2) Uani d . 1
C C1 0.35707(9) 0.75928(10) 0.41992(14) 0.0241(3) Uani d . 1
H H1A 0.3939 0.7496 0.3376 0.029 Uiso calc R 1
H H1B 0.3023 0.7152 0.4152 0.029 Uiso calc R 1
C C2 0.41390(11) 0.73488(12) 0.54424(15) 0.0323(3) Uani d . 1
H H2A 0.4793 0.7268 0.5202 0.039 Uiso calc R 1
H H2B 0.3922 0.6714 0.5863 0.039 Uiso calc R 1
C C3 0.40131(10) 0.82444(12) 0.64053(15) 0.0309(3) Uani d . 1
H H3A 0.3884 0.8004 0.7326 0.037 Uiso calc R 1
H H3B 0.4569 0.8674 0.6423 0.037 Uiso calc R 1
C C4 0.32014(9) 0.88251(11) 0.58455(13) 0.0242(3) Uani d . 1
H H4A 0.2616 0.8540 0.6174 0.029 Uiso calc R 1
H H4B 0.3234 0.9549 0.6097 0.029 Uiso calc R 1
C C5 0.40372(8) 0.93610(10) 0.38042(13) 0.0209(3) Uani d . 1
H H5A 0.4045 0.9315 0.2824 0.031 Uiso calc R 1
H H5B 0.4631 0.9141 0.4161 0.031 Uiso calc R 1
H H5C 0.3922 1.0063 0.4072 0.031 Uiso calc R 1
C C6 0.23958(8) 0.88722(10) 0.36358(13) 0.0198(3) Uani d . 1
H H6A 0.1941 0.8374 0.3962 0.024 Uiso calc R 1
H H6B 0.2487 0.8750 0.2666 0.024 Uiso calc R 1
C C7 0.20062(9) 0.99281(11) 0.38223(14) 0.0254(3) Uani d . 1
H H7A 0.1931 1.0073 0.4789 0.031 Uiso calc R 1
H H7B 0.2433 1.0434 0.3442 0.031 Uiso calc R 1
C C8 0.10858(10) 0.99984(12) 0.31221(18) 0.0372(4) Uani d . 1
H H8A 0.1173 0.9926 0.2153 0.056 Uiso calc R 1
H H8B 0.0806 1.0657 0.3313 0.056 Uiso calc R 1
H H8C 0.0683 0.9458 0.3447 0.056 Uiso calc R 1
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
Cl1 0.02343(18) 0.02619(19) 0.02308(18) -0.00399(13) -0.00151(13) -0.00178(12)
N1 0.0162(5) 0.0191(5) 0.0185(5) -0.0015(4) -0.0013(4) 0.0004(4)
C1 0.0246(7) 0.0178(6) 0.0299(7) 0.0005(5) -0.0008(6) 0.0012(5)
C2 0.0282(7) 0.0287(8) 0.0401(9) 0.0006(6) -0.0051(6) 0.0123(6)
C3 0.0273(7) 0.0406(9) 0.0247(7) -0.0068(6) -0.0067(6) 0.0100(6)
C4 0.0232(6) 0.0322(8) 0.0172(6) -0.0044(6) -0.0004(5) -0.0005(5)
C5 0.0163(6) 0.0223(7) 0.0241(6) -0.0031(5) 0.0008(5) 0.0023(5)
C6 0.0157(6) 0.0231(6) 0.0206(6) -0.0019(5) -0.0035(5) -0.0014(5)
C7 0.0208(6) 0.0257(7) 0.0298(7) 0.0018(5) -0.0037(6) -0.0049(6)
C8 0.0258(7) 0.0314(8) 0.0543(10) 0.0050(6) -0.0138(7) -0.0065(7)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 N1 C6 111.31(10)
C5 N1 C4 110.64(10)
C6 N1 C4 111.98(10)
C5 N1 C1 109.44(10)
C6 N1 C1 109.72(10)
C4 N1 C1 103.46(10)
N1 C1 C2 105.54(11)
N1 C1 H1A 110.6
C2 C1 H1A 110.6
N1 C1 H1B 110.6
C2 C1 H1B 110.6
H1A C1 H1B 108.8
C1 C2 C3 106.30(12)
C1 C2 H2A 110.5
C3 C2 H2A 110.5
C1 C2 H2B 110.5
C3 C2 H2B 110.5
H2A C2 H2B 108.7
C4 C3 C2 104.66(11)
C4 C3 H3A 110.8
C2 C3 H3A 110.8
C4 C3 H3B 110.8
C2 C3 H3B 110.8
H3A C3 H3B 108.9
N1 C4 C3 103.74(11)
N1 C4 H4A 111.0
C3 C4 H4A 111.0
N1 C4 H4B 111.0
C3 C4 H4B 111.0
H4A C4 H4B 109.0
N1 C5 H5A 109.5
N1 C5 H5B 109.5
H5A C5 H5B 109.5
N1 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N1 C6 C7 114.30(10)
N1 C6 H6A 108.7
C7 C6 H6A 108.7
N1 C6 H6B 108.7
C7 C6 H6B 108.7
H6A C6 H6B 107.6
C8 C7 C6 109.34(11)
C8 C7 H7A 109.8
C6 C7 H7A 109.8
C8 C7 H7B 109.8
C6 C7 H7B 109.8
H7A C7 H7B 108.3
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.5038(16)
N1 C6 1.5066(16)
N1 C4 1.5085(16)
N1 C1 1.5171(17)
C1 C2 1.526(2)
C1 H1A 0.9900
C1 H1B 0.9900
C2 C3 1.536(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.518(2)
C3 H3A 0.9900
C3 H3B 0.9900
C4 H4A 0.9900
C4 H4B 0.9900
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C7 1.5185(18)
C6 H6A 0.9900
C6 H6B 0.9900
C7 C8 1.5163(19)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
C1 H1B Cl1 2_565 0.99 2.79 3.6070(10) 141 y
C2 H2A Cl1 4_655 0.99 2.77 3.630(2) 146 y
C5 H5A Cl1 ? 0.98 2.77 3.6480(10) 149 y
C5 H5C Cl1 8_576 0.98 2.71 3.6560(10) 163 y
C6 H6A Cl1 2_565 0.99 2.76 3.6720(10) 153 y
C6 H6B Cl1 ? 0.99 2.77 3.6660(10) 151 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
C5 N1 C1 C2 85.97(12)
C6 N1 C1 C2 -151.63(11)
C4 N1 C1 C2 -31.99(13)
N1 C1 C2 C3 10.96(15)
C1 C2 C3 C4 14.09(15)
C5 N1 C4 C3 -76.14(13)
C6 N1 C4 C3 159.05(10)
C1 N1 C4 C3 40.98(12)
C2 C3 C4 N1 -33.99(14)
C5 N1 C6 C7 -63.82(14)
C4 N1 C6 C7 60.62(14)
C1 N1 C6 C7 174.90(11)
N1 C6 C7 C8 -177.02(12)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25934076
