##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# 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
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
1-(3-Phenylprop-2-ynyl)pyrrolidinium chloride
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H16 N +, Cl -'
_chemical_formula_sum     'C13 H16 Cl N'
_chemical_formula_iupac     'C13 H16 N +, Cl -'
_chemical_formula_weight     221.72
_chemical_melting_point     ?
_symmetry_cell_setting     Monoclinic
_symmetry_space_group_name_H-M     'P 21/c'
_symmetry_space_group_name_Hall     '-P 2ybc'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x, -y-1/2, z-1/2'
_cell_length_a     10.9504(2)
_cell_length_b     11.3553(3)
_cell_length_c     11.1951(2)
_cell_angle_alpha     90.00
_cell_angle_beta     117.0080(10)
_cell_angle_gamma     90.00
_cell_volume     1240.24(4)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     5548
_cell_measurement_theta_min     2.72
_cell_measurement_theta_max     28.08
_cell_measurement_temperature     298(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.10
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.187
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.276
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_exptl_special_details
;
 ?
;
_diffrn_ambient_temperature     298(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD area-detector'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     10560
_diffrn_reflns_av_R_equivalents     0.0541
_diffrn_reflns_av_sigmaI/netI     0.0306
_diffrn_reflns_theta_min     2.09
_diffrn_reflns_theta_max     25.99
_diffrn_reflns_theta_full     25.99
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -13
_diffrn_reflns_limit_h_max     13
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     2432
_reflns_number_gt     2353
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0693
_refine_ls_R_factor_gt     0.0672
_refine_ls_wR_factor_gt     0.1564
_refine_ls_wR_factor_ref     0.1578
_refine_ls_goodness_of_fit_ref     1.272
_refine_ls_restrained_S_all     1.272
_refine_ls_number_reflns     2432
_refine_ls_number_parameters     139
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0530P)²+0.6238P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_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     0.353
_refine_diff_density_min     -0.210
_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' 0.0033 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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2001)'
_computing_data_reduction     'SAINT (Bruker, 2001)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.6296(3) 0.8606(2) 0.7343(3) 0.0493(6) Uani d . 1 . .
    C C2 0.4916(3) 0.8723(3) 0.6473(3) 0.0620(7) Uani d . 1 . .
    H H2 0.4636 0.9243 0.5755 0.074 Uiso calc R 1 . .
    C C3 0.3957(3) 0.8078(3) 0.6660(4) 0.0735(9) Uani d . 1 . .
    H H3 0.3032 0.8162 0.6069 0.088 Uiso calc R 1 . .
    C C4 0.4359(4) 0.7315(3) 0.7707(4) 0.0774(10) Uani d . 1 . .
    H H4 0.3708 0.6878 0.7831 0.093 Uiso calc R 1 . .
    C C5 0.5724(4) 0.7188(3) 0.8581(4) 0.0734(9) Uani d . 1 . .
    H H5 0.5991 0.6663 0.9294 0.088 Uiso calc R 1 . .
    C C6 0.6697(3) 0.7830(2) 0.8413(3) 0.0590(7) Uani d . 1 . .
    H H6 0.7620 0.7746 0.9013 0.071 Uiso calc R 1 . .
    C C7 0.7303(3) 0.9288(2) 0.7156(3) 0.0551(7) Uani d . 1 . .
    C C8 0.8158(3) 0.9840(2) 0.7040(3) 0.0570(7) Uani d . 1 . .
    C C9 0.9214(3) 1.0575(2) 0.6955(3) 0.0581(7) Uani d . 1 . .
    H H9A 0.9276 1.1316 0.7410 0.070 Uiso calc R 1 . .
    H H9B 0.8952 1.0748 0.6021 0.070 Uiso calc R 1 . .
    C C10 1.1669(3) 1.0766(3) 0.7524(3) 0.0666(8) Uani d . 1 . .
    H H10A 1.1679 1.0699 0.6665 0.080 Uiso calc R 1 . .
    H H10B 1.1513 1.1584 0.7666 0.080 Uiso calc R 1 . .
    C C11 1.2991(3) 1.0342(3) 0.8625(3) 0.0759(9) Uani d . 1 . .
    H H11A 1.3503 1.0994 0.9190 0.091 Uiso calc R 1 . .
    H H11B 1.3545 0.9971 0.8258 0.091 Uiso calc R 1 . .
    C C12 1.2620(4) 0.9460(3) 0.9424(3) 0.0784(9) Uani d . 1 . .
    H H12A 1.2790 0.8662 0.9227 0.094 Uiso calc R 1 . .
    H H12B 1.3153 0.9601 1.0378 0.094 Uiso calc R 1 . .
    C C13 1.1110(3) 0.9647(3) 0.8992(3) 0.0640(8) Uani d . 1 . .
    H H13A 1.0679 0.8928 0.9081 0.077 Uiso calc R 1 . .
    H H13B 1.0967 1.0265 0.9513 0.077 Uiso calc R 1 . .
    Cl Cl1 0.03151(7) 0.70879(6) 0.07738(7) 0.0545(2) Uani d . 1 . .
    N N1 1.0572(2) 0.99964(19) 0.7561(2) 0.0491(5) Uani d D 1 . .
    H H1 1.051(3) 0.9386(17) 0.707(2) 0.059 Uiso d 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
    C1 0.0479(14) 0.0489(14) 0.0587(15) -0.0012(11) 0.0308(12) -0.0117(12)
    C2 0.0534(16) 0.0660(17) 0.0676(18) 0.0029(13) 0.0284(14) 0.0021(14)
    C3 0.0471(16) 0.082(2) 0.090(2) -0.0070(15) 0.0306(16) -0.0131(18)
    C4 0.079(2) 0.075(2) 0.103(3) -0.0238(18) 0.063(2) -0.019(2)
    C5 0.095(3) 0.0597(18) 0.078(2) -0.0041(16) 0.051(2) 0.0032(15)
    C6 0.0556(16) 0.0596(17) 0.0616(17) 0.0044(13) 0.0265(14) -0.0063(13)
    C7 0.0528(15) 0.0557(15) 0.0642(17) -0.0009(12) 0.0329(14) -0.0069(12)
    C8 0.0559(16) 0.0579(16) 0.0628(17) -0.0023(13) 0.0317(14) -0.0067(13)
    C9 0.0617(17) 0.0524(15) 0.0664(18) -0.0038(13) 0.0345(15) -0.0002(13)
    C10 0.0595(17) 0.0709(19) 0.0699(19) -0.0164(14) 0.0297(15) 0.0096(15)
    C11 0.0622(19) 0.095(2) 0.070(2) -0.0112(17) 0.0293(17) -0.0061(18)
    C12 0.080(2) 0.085(2) 0.0586(18) 0.0083(18) 0.0219(17) 0.0059(16)
    C13 0.081(2) 0.0623(17) 0.0562(17) -0.0052(15) 0.0383(16) 0.0044(13)
    Cl1 0.0537(4) 0.0555(4) 0.0528(4) 0.0018(3) 0.0228(3) 0.0045(3)
    N1 0.0566(13) 0.0470(12) 0.0498(12) -0.0099(10) 0.0296(11) -0.0019(9)
_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
    C1 C2 . 1.383(4) ?
    C1 C6 . 1.388(4) ?
    C1 C7 . 1.439(4) ?
    C2 C3 . 1.372(4) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.360(5) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.372(5) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.373(4) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.182(4) ?
    C8 C9 . 1.465(4) ?
    C9 N1 . 1.479(4) ?
    C9 H9A . 0.9700 ?
    C9 H9B . 0.9700 ?
    C10 C11 . 1.492(5) ?
    C10 N1 . 1.501(3) ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C11 C12 . 1.516(5) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C12 C13 . 1.512(5) ?
    C12 H12A . 0.9700 ?
    C12 H12B . 0.9700 ?
    C13 N1 . 1.488(3) ?
    C13 H13A . 0.9700 ?
    C13 H13B . 0.9700 ?
    N1 H1 . 0.868(10) ?
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
    C2 C1 C6 . . 119.1(3) ?
    C2 C1 C7 . . 120.7(3) ?
    C6 C1 C7 . . 120.3(3) ?
    C3 C2 C1 . . 120.6(3) ?
    C3 C2 H2 . . 119.7 ?
    C1 C2 H2 . . 119.7 ?
    C4 C3 C2 . . 120.1(3) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 120.2(3) ?
    C3 C4 H4 . . 119.9 ?
    C5 C4 H4 . . 119.9 ?
    C4 C5 C6 . . 120.6(3) ?
    C4 C5 H5 . . 119.7 ?
    C6 C5 H5 . . 119.7 ?
    C5 C6 C1 . . 119.6(3) ?
    C5 C6 H6 . . 120.2 ?
    C1 C6 H6 . . 120.2 ?
    C8 C7 C1 . . 178.0(3) ?
    C7 C8 C9 . . 176.5(3) ?
    C8 C9 N1 . . 112.1(2) ?
    C8 C9 H9A . . 109.2 ?
    N1 C9 H9A . . 109.2 ?
    C8 C9 H9B . . 109.2 ?
    N1 C9 H9B . . 109.2 ?
    H9A C9 H9B . . 107.9 ?
    C11 C10 N1 . . 106.1(2) ?
    C11 C10 H10A . . 110.5 ?
    N1 C10 H10A . . 110.5 ?
    C11 C10 H10B . . 110.5 ?
    N1 C10 H10B . . 110.5 ?
    H10A C10 H10B . . 108.7 ?
    C10 C11 C12 . . 106.3(3) ?
    C10 C11 H11A . . 110.5 ?
    C12 C11 H11A . . 110.5 ?
    C10 C11 H11B . . 110.5 ?
    C12 C11 H11B . . 110.5 ?
    H11A C11 H11B . . 108.7 ?
    C13 C12 C11 . . 105.4(3) ?
    C13 C12 H12A . . 110.7 ?
    C11 C12 H12A . . 110.7 ?
    C13 C12 H12B . . 110.7 ?
    C11 C12 H12B . . 110.7 ?
    H12A C12 H12B . . 108.8 ?
    N1 C13 C12 . . 102.8(2) ?
    N1 C13 H13A . . 111.2 ?
    C12 C13 H13A . . 111.2 ?
    N1 C13 H13B . . 111.2 ?
    C12 C13 H13B . . 111.2 ?
    H13A C13 H13B . . 109.1 ?
    C9 N1 C13 . . 115.9(2) ?
    C9 N1 C10 . . 112.3(2) ?
    C13 N1 C10 . . 104.7(2) ?
    C9 N1 H1 . . 107(2) ?
    C13 N1 H1 . . 110(2) ?
    C10 N1 H1 . . 106.3(19) ?
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
    C6 H6 Cl1 1_656 0.93 2.81 3.726(3) 170.4
    C9 H9A Cl1 3_676 0.97 2.61 3.547(3) 163.6
    N1 H1 Cl1 4_676 0.868(10) 2.161(10) 3.028(2) 178(3)
data_global
_journal_date_recd_electronic     2009-09-09
_journal_date_accepted     2009-10-15
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2806
_journal_page_last     o2806
_journal_paper_category     QO
_journal_coeditor_code     PB2009
_publ_contact_author_name     'Tao Pang'
_publ_contact_author_address
;
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education
College of Chemistry
Central China Normal University
Wuhan  430079
People's Republic of China
;
_publ_contact_author_email     leileitaotao6666@163.com
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
1-(3-Phenylprop-2-ynyl)pyrrolidinium chloride
;
loop_
    _publ_author_name
    _publ_author_address
    'Pang, Tao'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Lu, Hui'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
    'Pang, Tao'
;
Key Laboratory of Pesticides and Chemical Biology of the Ministry of Education
College of Chemistry
Central China Normal University
Wuhan 430079
People's Republic of China
;
