##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section C. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica 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.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_database_code_depnum_ccdc_archive 'CCDC 1411976'
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;
1-(1-Oxo-1-phenylpentan-2-yl)pyrrolidin-1-ium chloride 0.786-hydrate
;
_chemical_name_common     'Alpha-pyrrolidinopentiophenone chloride hydrate'
_chemical_formula_moiety     'C15 H22 N O +, Cl -, 0.786(H2 O)'
_chemical_formula_sum     'C15 H23.57 Cl N O1.79'
_chemical_formula_iupac     'C15 H22 N O + , Cl - , 0.786H2 O'
_chemical_formula_weight     281.95
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/c'
_space_group_name_Hall     '-P 2ybc'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     13.9428(3)
_cell_length_b     9.3285(2)
_cell_length_c     13.6865(3)
_cell_angle_alpha     90
_cell_angle_beta     119.2730(10)
_cell_angle_gamma     90
_cell_volume     1552.82(6)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     8883
_cell_measurement_theta_min     3.63
_cell_measurement_theta_max     68.35
_cell_measurement_temperature     100(2)
_exptl_crystal_description     paralellepiped
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.589
_exptl_crystal_size_mid     0.130
_exptl_crystal_size_min     0.068
_exptl_crystal_density_diffrn     1.206
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     607.4
_exptl_absorpt_coefficient_mu     2.143
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2009)
;
_shelx_estimated_absorpt_T_min     0.363
_shelx_estimated_absorpt_T_max     0.867
_exptl_absorpt_correction_T_min     0.363
_exptl_absorpt_correction_T_max     0.867
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_device_type     'Bruker APEXII CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     14334
_diffrn_reflns_av_R_equivalents     0.0320
_diffrn_reflns_theta_min     3.634
_diffrn_reflns_theta_max     68.630
_diffrn_reflns_theta_full     67.679
_diffrn_measured_fraction_theta_max     0.961
_diffrn_measured_fraction_theta_full     0.975
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -16
_diffrn_reflns_limit_l_max     16
_refine_special_details     ?
_reflns_number_total     2756
_reflns_number_gt     2455
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0529
_refine_ls_R_factor_gt     0.0475
_refine_ls_wR_factor_gt     0.1110
_refine_ls_wR_factor_ref     0.1150
_refine_ls_goodness_of_fit_ref     1.088
_refine_ls_restrained_S_all     1.088
_refine_ls_number_reflns     2756
_refine_ls_number_parameters     183
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
            'w = 1/[σ²(Fo²)+(0.0389P)²+1.8447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_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     1.345
_refine_diff_density_min     -0.844
_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' 0.0181 0.0091
                         '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' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Cl' 'Cl' 0.3639 0.7018
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
APEX2 (Bruker, 2009)
;
_computing_cell_refinement
;
SAINT (Bruker, 2009)
;
_computing_data_reduction
;
SAINT (Bruker, 2009)
;
_computing_structure_solution
;
SHELXT 2014/4 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
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
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.13431(5) 0.13435(7) 0.16898(4) 0.03800(19) Uani d 1 . .
    O O1 0.33489(13) 0.05219(16) 0.47174(12) 0.0293(4) Uani d 1 . .
    O O2 -0.10932(18) 0.1425(3) -0.00914(19) 0.0378(8) Uani d 0.786(7) . .
    H H2A -0.041(4) 0.139(4) 0.038(4) 0.057 Uiso d 0.786(7) . .
    H H2B -0.116(3) 0.075(5) -0.053(4) 0.057 Uiso d 0.786(7) . .
    N N1 0.14861(14) 0.1979(2) 0.39803(15) 0.0239(4) Uani d 1 . .
    H H1 0.1652(19) 0.175(3) 0.341(2) 0.029 Uiso d 1 . .
    C C1 0.34224(18) 0.1502(2) 0.53401(17) 0.0232(5) Uani d 1 . .
    C C2 0.44313(17) 0.1747(2) 0.64323(17) 0.0228(4) Uani d 1 . .
    C C3 0.54176(18) 0.1163(2) 0.65872(19) 0.0260(5) Uani d 1 . .
    H H3 0.5430 0.0636 0.6000 0.031 Uiso calc 1 . .
    C C4 0.63772(19) 0.1351(2) 0.7594(2) 0.0296(5) Uani d 1 . .
    H H4 0.7048 0.0952 0.7697 0.036 Uiso calc 1 . .
    C C5 0.63592(19) 0.2122(2) 0.84538(19) 0.0298(5) Uani d 1 . .
    H H5 0.7018 0.2251 0.9145 0.036 Uiso calc 1 . .
    C C6 0.53846(19) 0.2702(2) 0.83053(18) 0.0293(5) Uani d 1 . .
    H H6 0.5376 0.3223 0.8897 0.035 Uiso calc 1 . .
    C C7 0.44182(18) 0.2529(2) 0.72969(17) 0.0263(5) Uani d 1 . .
    H H7 0.3752 0.2940 0.7195 0.032 Uiso calc 1 . .
    C C8 0.24840(17) 0.2574(2) 0.49774(17) 0.0224(4) Uani d 1 . .
    H H8 0.2316 0.2699 0.5604 0.027 Uiso calc 1 . .
    C C9 0.28388(17) 0.4024(2) 0.47324(18) 0.0244(5) Uani d 1 . .
    H H9A 0.2209 0.4694 0.4460 0.029 Uiso calc 1 . .
    H H9B 0.3436 0.4417 0.5442 0.029 Uiso calc 1 . .
    C C10 0.32375(18) 0.3978(2) 0.38745(19) 0.0281(5) Uani d 1 . .
    H H10A 0.3871 0.3317 0.4140 0.034 Uiso calc 1 . .
    H H10B 0.2642 0.3604 0.3155 0.034 Uiso calc 1 . .
    C C11 0.3578(2) 0.5459(3) 0.3688(2) 0.0369(6) Uani d 1 . .
    H H11A 0.2942 0.6104 0.3392 0.055 Uiso calc 1 . .
    H H11B 0.3850 0.5391 0.3151 0.055 Uiso calc 1 . .
    H H11C 0.4161 0.5836 0.4401 0.055 Uiso calc 1 . .
    C C12 0.10420(19) 0.0616(3) 0.4229(2) 0.0315(5) Uani d 1 . .
    H H12A 0.1437 0.0405 0.5042 0.038 Uiso calc 1 . .
    H H12B 0.1125 -0.0211 0.3823 0.038 Uiso calc 1 . .
    C C13 -0.01692(19) 0.0917(3) 0.3826(2) 0.0337(6) Uani d 1 . .
    H H13A -0.0618 0.0044 0.3503 0.040 Uiso calc 1 . .
    H H13B -0.0277 0.1265 0.4449 0.040 Uiso calc 1 . .
    C C14 -0.04728(19) 0.2071(3) 0.29364(19) 0.0325(5) Uani d 1 . .
    H H14A -0.0592 0.1660 0.2219 0.039 Uiso calc 1 . .
    H H14B -0.1139 0.2602 0.2808 0.039 Uiso calc 1 . .
    C C15 0.05371(18) 0.3022(3) 0.34626(19) 0.0288(5) Uani d 1 . .
    H H15A 0.0580 0.3623 0.2889 0.035 Uiso calc 1 . .
    H H15B 0.0529 0.3654 0.4040 0.035 Uiso calc 1 . .
_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.
;
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
    O1 C1 . 1.219(3) ?
    O2 H2A . 0.84(5) ?
    O2 H2B . 0.85(5) ?
    N1 C8 . 1.500(3) ?
    N1 C15 . 1.511(3) ?
    N1 C12 . 1.524(3) ?
    N1 H1 . 0.94(3) ?
    C1 C2 . 1.486(3) ?
    C1 C8 . 1.525(3) ?
    C2 C3 . 1.396(3) ?
    C2 C7 . 1.398(3) ?
    C3 C4 . 1.384(3) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.391(3) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.382(3) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.388(3) ?
    C6 H6 . 0.9500 ?
    C7 H7 . 0.9500 ?
    C8 C9 . 1.533(3) ?
    C8 H8 . 1.0000 ?
    C9 C10 . 1.526(3) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.522(3) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9800 ?
    C11 H11B . 0.9800 ?
    C11 H11C . 0.9800 ?
    C12 C13 . 1.524(3) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.522(3) ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C15 . 1.515(3) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
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
    H2A O2 H2B . . 102(4) ?
    C8 N1 C15 . . 113.49(17) ?
    C8 N1 C12 . . 113.76(16) ?
    C15 N1 C12 . . 106.48(16) ?
    C8 N1 H1 . . 110.0(15) ?
    C15 N1 H1 . . 105.8(15) ?
    C12 N1 H1 . . 106.7(15) ?
    O1 C1 C2 . . 122.23(19) ?
    O1 C1 C8 . . 119.93(19) ?
    C2 C1 C8 . . 117.76(17) ?
    C3 C2 C7 . . 119.7(2) ?
    C3 C2 C1 . . 118.05(18) ?
    C7 C2 C1 . . 122.29(19) ?
    C4 C3 C2 . . 120.2(2) ?
    C4 C3 H3 . . 119.9 ?
    C2 C3 H3 . . 119.9 ?
    C3 C4 C5 . . 119.9(2) ?
    C3 C4 H4 . . 120.0 ?
    C5 C4 H4 . . 120.0 ?
    C6 C5 C4 . . 120.1(2) ?
    C6 C5 H5 . . 119.9 ?
    C4 C5 H5 . . 119.9 ?
    C5 C6 C7 . . 120.5(2) ?
    C5 C6 H6 . . 119.8 ?
    C7 C6 H6 . . 119.8 ?
    C6 C7 C2 . . 119.6(2) ?
    C6 C7 H7 . . 120.2 ?
    C2 C7 H7 . . 120.2 ?
    N1 C8 C1 . . 108.67(17) ?
    N1 C8 C9 . . 112.49(17) ?
    C1 C8 C9 . . 109.46(16) ?
    N1 C8 H8 . . 108.7 ?
    C1 C8 H8 . . 108.7 ?
    C9 C8 H8 . . 108.7 ?
    C10 C9 C8 . . 114.93(17) ?
    C10 C9 H9A . . 108.5 ?
    C8 C9 H9A . . 108.5 ?
    C10 C9 H9B . . 108.5 ?
    C8 C9 H9B . . 108.5 ?
    H9A C9 H9B . . 107.5 ?
    C11 C10 C9 . . 111.35(19) ?
    C11 C10 H10A . . 109.4 ?
    C9 C10 H10A . . 109.4 ?
    C11 C10 H10B . . 109.4 ?
    C9 C10 H10B . . 109.4 ?
    H10A C10 H10B . . 108.0 ?
    C10 C11 H11A . . 109.5 ?
    C10 C11 H11B . . 109.5 ?
    H11A C11 H11B . . 109.5 ?
    C10 C11 H11C . . 109.5 ?
    H11A C11 H11C . . 109.5 ?
    H11B C11 H11C . . 109.5 ?
    N1 C12 C13 . . 105.34(19) ?
    N1 C12 H12A . . 110.7 ?
    C13 C12 H12A . . 110.7 ?
    N1 C12 H12B . . 110.7 ?
    C13 C12 H12B . . 110.7 ?
    H12A C12 H12B . . 108.8 ?
    C14 C13 C12 . . 104.20(18) ?
    C14 C13 H13A . . 110.9 ?
    C12 C13 H13A . . 110.9 ?
    C14 C13 H13B . . 110.9 ?
    C12 C13 H13B . . 110.9 ?
    H13A C13 H13B . . 108.9 ?
    C15 C14 C13 . . 101.74(18) ?
    C15 C14 H14A . . 111.4 ?
    C13 C14 H14A . . 111.4 ?
    C15 C14 H14B . . 111.4 ?
    C13 C14 H14B . . 111.4 ?
    H14A C14 H14B . . 109.3 ?
    N1 C15 C14 . . 104.08(19) ?
    N1 C15 H15A . . 110.9 ?
    C14 C15 H15A . . 110.9 ?
    N1 C15 H15B . . 110.9 ?
    C14 C15 H15B . . 110.9 ?
    H15A C15 H15B . . 109.0 ?
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
    O1 C1 C2 C3 . . . . 20.9(3) ?
    C8 C1 C2 C3 . . . . -155.68(18) ?
    O1 C1 C2 C7 . . . . -158.8(2) ?
    C8 C1 C2 C7 . . . . 24.6(3) ?
    C7 C2 C3 C4 . . . . 0.3(3) ?
    C1 C2 C3 C4 . . . . -179.35(19) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C3 C4 C5 C6 . . . . 0.0(3) ?
    C4 C5 C6 C7 . . . . -0.4(3) ?
    C5 C6 C7 C2 . . . . 0.8(3) ?
    C3 C2 C7 C6 . . . . -0.7(3) ?
    C1 C2 C7 C6 . . . . 178.94(19) ?
    C15 N1 C8 C1 . . . . -173.42(16) ?
    C12 N1 C8 C1 . . . . 64.6(2) ?
    C15 N1 C8 C9 . . . . -52.1(2) ?
    C12 N1 C8 C9 . . . . -174.02(17) ?
    O1 C1 C8 N1 . . . . 14.0(3) ?
    C2 C1 C8 N1 . . . . -169.29(16) ?
    O1 C1 C8 C9 . . . . -109.2(2) ?
    C2 C1 C8 C9 . . . . 67.5(2) ?
    N1 C8 C9 C10 . . . . -65.5(2) ?
    C1 C8 C9 C10 . . . . 55.4(2) ?
    C8 C9 C10 C11 . . . . -179.70(19) ?
    C8 N1 C12 C13 . . . . 126.51(19) ?
    C15 N1 C12 C13 . . . . 0.7(2) ?
    N1 C12 C13 C14 . . . . 24.7(2) ?
    C12 C13 C14 C15 . . . . -40.5(2) ?
    C8 N1 C15 C14 . . . . -151.95(17) ?
    C12 N1 C15 C14 . . . . -26.0(2) ?
    C13 C14 C15 N1 . . . . 40.9(2) ?
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
    N1 H1 Cl1 1_555 0.94(3) 2.21(3) 3.0997(18) 157(2) yes
    O2 H2A Cl1 1_555 0.84(5) 2.22(5) 3.064(2) 176(4) yes
    O2 H2B Cl1 3_555 0.85(5) 2.45(5) 3.291(3) 175(4) yes
data_global
_journal_date_recd_electronic     2015-10-25
_journal_date_accepted     2015-12-09
_journal_name_full     'Acta Crystallographica, Section C'
_journal_year     2016
_journal_volume     72
_journal_issue      1
_journal_page_first     48
_journal_page_last     51
_journal_paper_category     FA
_journal_paper_doi     10.1107/S2053229615023621
_journal_coeditor_code     LG3180
_publ_contact_author_name     'Roger A. Lalancette'
_publ_contact_author_address
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark
NJ 07102
USA
;
_publ_contact_author_email     rogerlal@andromeda.rutgers.edu
_publ_contact_author_fax     973-353-1264
_publ_contact_author_phone     973-353-5646
_publ_section_title
;
The dangerous new synthetic drug α-PVP as the hydrated chloride salt
α-pyrrolidinopentiophenone hydrochloride 0.786-hydrate
;
loop_
    _publ_author_name
    _publ_author_address
    'Wood, Matthew R.'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark
NJ 07102
USA
;
    'Bernal, Ivan'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark
NJ 07102
USA
;
    'Lalancette, Roger A.'
;
Carl A. Olson Memorial Laboratories
Department of Chemistry
Rutgers University
Newark
NJ 07102
USA
;
_publ_section_synopsis
;
The dangerous new drug, α-PVP, crystallizes as the chloride salt with slightly
less than a full solvent water molecule, forming hydrogen bonds between each
of the water H atoms and the chloride ion, which is itself hydrogen-bonded to
the quaternary N atom of the drug cation. A comparison with the structure of a
number of other bath salts shows that, even though the bond between the phenyl
group and the ketone group has free rotation, the conformation is essentially
always the same.
;
