#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/53/2215373.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_2215373
loop_
_publ_author_name
'Sebastian Herler'
'Peter Mayer'
'Axel Schulz'
'Alexander Villinger'
_publ_section_title
;
 N-Methyl-2-pyrrolidone hydrochloride
;
_journal_coeditor_code           BT2495
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3991
_journal_page_last               o3991
_journal_paper_doi               10.1107/S1600536807042997
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C5 H10 N O + , Cl -'
_chemical_formula_moiety         'C5 H10 N O + , Cl -'
_chemical_formula_sum            'C5 H10 Cl N O'
_chemical_formula_weight         135.59
_chemical_name_common            'N-Methyl-2-pyrrolidone hydrochloride'
_chemical_name_systematic
;
N-Methyl-2-pyrrolidone hydrochloride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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            4
_cell_length_a                   6.1391(2)
_cell_length_b                   8.9537(2)
_cell_length_c                   12.5976(4)
_cell_measurement_reflns_used    4313
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.713
_cell_measurement_theta_min      3.134
_cell_volume                     692.46(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 1999)'
_computing_data_reduction
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
Windows version (Farrugia, 1997) of
ORTEPIII (Burnett & Johnson, 1996)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution
;
SIR97 (Altomare et al.,  1999)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       phi/omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0938
_diffrn_reflns_av_sigmaI/netI    0.0411
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8273
_diffrn_reflns_theta_full        24.74
_diffrn_reflns_theta_max         24.74
_diffrn_reflns_theta_min         3.23
_exptl_absorpt_coefficient_mu    0.459
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.203
_refine_ls_abs_structure_details 'Flack (1983), 471 Friedel pairs'
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0297
_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)+(0.0310P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0702
_refine_ls_wR_factor_ref         0.0722
_reflns_number_gt                1124
_reflns_number_total             1192
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2495.cif
_cod_data_source_block           I
_cod_database_code               2215373
_cod_database_fobs_code          2215373
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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_occupancy
Cl Cl 0.98418(9) 1.03603(5) 0.63590(4) 0.04228(18) Uani d 1
O O 1.0110(3) 0.73233(15) 0.57419(11) 0.0400(3) Uani d 1
N N 0.8324(3) 0.51346(18) 0.59226(13) 0.0323(4) Uani d 1
C C1 0.8497(3) 0.6551(2) 0.61169(14) 0.0305(4) Uani d 1
C C2 0.6698(4) 0.7117(2) 0.67914(17) 0.0363(5) Uani d 1
C C3 0.5168(5) 0.5788(3) 0.6863(2) 0.0553(6) Uani d 1
C C4 0.6445(4) 0.4457(3) 0.64539(19) 0.0413(5) Uani d 1
C C5 0.9858(5) 0.4241(3) 0.5312(2) 0.0445(5) Uani d 1
H H41 0.568(4) 0.387(3) 0.5962(18) 0.043(7) Uiso d 1
H H21 0.612(4) 0.803(3) 0.647(2) 0.054(7) Uiso d 1
H H31 0.479(5) 0.559(3) 0.752(3) 0.080(9) Uiso d 1
H H22 0.724(4) 0.743(3) 0.745(2) 0.056(7) Uiso d 1
H H51 1.018(6) 0.342(4) 0.571(3) 0.092(11) Uiso d 1
H H42 0.701(4) 0.380(3) 0.702(2) 0.051(7) Uiso d 1
H H52 0.914(6) 0.383(4) 0.472(3) 0.092(11) Uiso d 1
H H32 0.389(6) 0.591(4) 0.641(3) 0.098(12) Uiso d 1
H H53 1.106(5) 0.480(3) 0.511(2) 0.059(8) Uiso d 1
H H 0.994(6) 0.843(4) 0.596(3) 0.094(10) Uiso d 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
Cl 0.0466(3) 0.0332(3) 0.0470(3) -0.0062(2) -0.0023(3) -0.0018(2)
O 0.0382(8) 0.0316(7) 0.0502(8) -0.0046(8) 0.0125(7) 0.0001(6)
N 0.0339(9) 0.0299(9) 0.0331(8) -0.0008(7) 0.0029(7) -0.0009(7)
C1 0.0298(10) 0.0314(10) 0.0302(10) -0.0018(8) -0.0012(8) 0.0026(7)
C2 0.0348(11) 0.0390(12) 0.0351(11) 0.0037(9) 0.0035(9) -0.0005(9)
C3 0.0445(15) 0.0556(14) 0.0657(16) -0.0099(14) 0.0194(14) -0.0082(12)
C4 0.0417(11) 0.0408(13) 0.0414(11) -0.0127(10) 0.0023(11) 0.0017(11)
C5 0.0469(13) 0.0338(11) 0.0526(13) 0.0048(12) 0.0086(13) -0.0041(10)
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.120000
-1 0 0 0.130000
0 1 0 0.100000
0 -1 0 0.100000
-2 -3 9 0.100000
2 3 -9 0.100000
2 3 4 0.150000
-2 -3 -4 0.150000
1 1 11 0.130000
-1 -1 -11 0.120000
-1 2 4 0.120000
1 -2 -4 0.120000
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
C1 O H 110(2) n
C1 N C5 125.78(19) n
C1 N C4 112.53(16) n
C5 N C4 121.57(18) n
N C1 O 121.02(18) n
N C1 C2 112.45(17) n
O C1 C2 126.52(18) n
C1 C2 C3 103.08(18) n
C1 C2 H21 108.9(15) ?
C3 C2 H21 117.0(15) ?
C1 C2 H22 110.2(16) ?
C3 C2 H22 113.6(16) ?
H21 C2 H22 104(2) ?
C4 C3 C2 106.0(2) n
C4 C3 H31 107(2) ?
C2 C3 H31 112(2) ?
C4 C3 H32 108(2) ?
C2 C3 H32 112(2) ?
H31 C3 H32 111(3) ?
N C4 C3 103.71(17) n
N C4 H41 108.8(14) ?
C3 C4 H41 114.0(15) ?
N C4 H42 107.5(15) ?
C3 C4 H42 113.9(14) ?
H41 C4 H42 108.6(19) ?
N C5 H51 107(2) ?
N C5 H52 109(2) ?
H51 C5 H52 103(3) ?
N C5 H53 111.6(18) ?
H51 C5 H53 114(3) ?
H52 C5 H53 111(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl H 1.80(4) n
O C1 1.297(3) n
O H 1.03(4) n
N C1 1.296(3) n
N C5 1.455(3) n
N C4 1.465(3) n
C1 C2 1.483(3) n
C2 C3 1.519(3) n
C2 H21 0.98(3) n
C2 H22 0.93(3) n
C3 C4 1.516(3) n
C3 H31 0.87(3) n
C3 H32 0.98(4) n
C4 H41 0.94(2) n
C4 H42 0.99(2) n
C5 H51 0.91(3) n
C5 H52 0.94(4) n
C5 H53 0.93(3) n
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O H Cl 1.03(4) 1.80(4) 2.8330(14) 176(3)
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
C5 N C1 O 1.6(3) n
C4 N C1 O 177.57(19) n
C5 N C1 C2 -178.2(2) n
C4 N C1 C2 -2.2(2) n
N C1 C2 C3 -7.4(3) n
O C1 C2 C3 172.9(2) n
C1 C2 C3 C4 13.4(3) n
C1 N C4 C3 10.8(3) n
C5 N C4 C3 -173.1(2) n
C2 C3 C4 N -14.6(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13323000
