##############################################################################
###                                                                        ###
###        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 2.1.    #
#                                                                            #
# 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                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
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##############################################################################
                                             
data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2005-01-18
_journal_date_accepted     2005-01-31
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      3
_journal_page_first     o585
_journal_page_last     o586
_journal_paper_category     EO
_publ_contact_author_name     'Prof. Massimo Di Vaira'
_publ_contact_author_address
;
Dipartimento di Chimica
Universitá di Firenze
Via della Lastruccia 3
I-50019 Sesto Fiorentino
Firenze, Italy
;
_publ_contact_author_email     massimo.divaira@unifi.it
_publ_contact_author_phone     '+39 (0)55 4573278 '
_publ_section_title
;
(R)-(-)-Mepivacaine hydrochloride enantiomer, a low-temperature study
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Bambagiotti Alberti, Massimo' .
;
Dipartimento di Scienze Farmaceutiche
Universitá di Firenze
Via U. Schiff 6
I-50019 Sesto Fiorentino
Firenze, Italy
;
    'Bruni, Bruno' .
;
Dipartimento di Chimica
Universitá di Firenze
Via della Lastruccia 3
I-50019 Sesto Fiorentino
Firenze, Italy
;
    'Di Vaira, Massimo' .
;
Dipartimento di Chimica
Universitá di Firenze
Via della Lastruccia 3
I-50019 Sesto Fiorentino
Firenze, Italy
;
    'Giannellini, Valerio' .
;
Dipartimento di Scienze Farmaceutiche
Universitá di Firenze
Via U. Schiff 6
I-50019 Sesto Fiorentino
Firenze, Italy
;
data_I
_chemical_name_systematic
;
(2R)-2-(2,6-dimethylphenylaminocarbonyl)-1-methylpiperidinium chloride
;
_chemical_name_common     'mepivacaine hydrochloride'
_chemical_formula_moiety     'C15 H23 N2 O +, Cl -'
_chemical_formula_sum     'C15 H23 Cl N2 O'
_chemical_formula_iupac     'C15 H23 N2 O +, Cl -'
_chemical_formula_weight     282.80
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P 21 21 21'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, -y, z+1/2'
    '-x, y+1/2, -z+1/2'
    'x+1/2, -y+1/2, -z'
_cell_length_a     9.7378(10)
_cell_length_b     10.5790(9)
_cell_length_c     15.2761(15)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1573.7(3)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     952
_cell_measurement_theta_min     6
_cell_measurement_theta_max     58
_cell_measurement_temperature     180(2)
_exptl_crystal_description     'elongated prism'
_exptl_crystal_colour     colorless
_exptl_crystal_size_max     0.80
_exptl_crystal_size_mid     0.30
_exptl_crystal_size_min     0.30
_exptl_crystal_density_diffrn     1.194
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     608
_exptl_absorpt_coefficient_mu     2.098
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1986)'
_exptl_absorpt_correction_T_min     0.331
_exptl_absorpt_correction_T_max     0.533
_exptl_special_details
;
;
_diffrn_ambient_temperature     180(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Oxford Diffraction CCD'
_diffrn_measurement_method     ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6079
_diffrn_reflns_av_R_equivalents     0.0295
_diffrn_reflns_av_sigmaI/netI     0.0429
_diffrn_reflns_theta_min     5.09
_diffrn_reflns_theta_max     59.03
_diffrn_reflns_theta_full     59.03
_diffrn_measured_fraction_theta_max     0.981
_diffrn_measured_fraction_theta_full     0.981
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     9
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     16
_diffrn_standards_number     0
_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     2201
_reflns_number_gt     1989
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0243
_refine_ls_R_factor_gt     0.0224
_refine_ls_wR_factor_gt     0.0465
_refine_ls_wR_factor_ref     0.0468
_refine_ls_goodness_of_fit_ref     0.956
_refine_ls_restrained_S_all     0.956
_refine_ls_number_reflns     2201
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refxyz
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
             'calc w = 1/[σ²(Fo²)+(0.0218P)²] 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     0.137
_refine_diff_density_min     -0.109
_refine_ls_extinction_method     SHELXL97
_refine_ls_extinction_coef     0.0167(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 883 Friedel pairs'
_refine_ls_abs_structure_Flack     0.023(11)
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'
    'Cl' 'Cl' 0.3639 0.7018
                         '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'
_computing_data_collection     'CrysAlis CCD (Oxford Diffraction, 2001)'
_computing_cell_refinement     'CrysAlis CCD'
_computing_data_reduction     'CrysAlis RED (Oxford Diffraction, 2001)'
_computing_structure_solution     'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material     SHELXL97
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
    Cl 0.21641(4) 0.51729(4) 0.87349(3) 0.03400(15) Uani d . 1 . . Cl
    N1 -0.09933(14) 0.26043(15) 0.69728(9) 0.0246(4) Uani d . 1 . . N
    H1N -0.1038(18) 0.1807(17) 0.6759(11) 0.029 Uiso d . 1 . . H
    C1' -0.1655(2) 0.2570(3) 0.78545(13) 0.0377(5) Uani d . 1 . . C
    H71 -0.114(2) 0.199(2) 0.8240(13) 0.057 Uiso d . 1 . . H
    H72 -0.256(2) 0.216(2) 0.7769(13) 0.057 Uiso d . 1 . . H
    H73 -0.172(2) 0.340(2) 0.8081(14) 0.057 Uiso d . 1 . . H
    C2 0.04679(18) 0.30285(18) 0.70399(11) 0.0260(4) Uani d . 1 . . C
    H2 0.0474(17) 0.3791(18) 0.7346(12) 0.031 Uiso d . 1 . . H
    C3 0.1101(2) 0.3215(2) 0.61335(13) 0.0387(5) Uani d . 1 . . C
    H31 0.118(2) 0.237(2) 0.5860(12) 0.046 Uiso d . 1 . . H
    H32 0.199(2) 0.3595(17) 0.6236(12) 0.046 Uiso d . 1 . . H
    C4 0.0237(2) 0.4076(2) 0.55541(15) 0.0427(6) Uani d . 1 . . C
    H41 0.022(2) 0.490(2) 0.5813(13) 0.051 Uiso d . 1 . . H
    H42 0.066(2) 0.415(2) 0.4989(14) 0.051 Uiso d . 1 . . H
    C5 -0.1190(2) 0.3523(2) 0.54786(13) 0.0358(5) Uani d . 1 . . C
    H51 -0.182(2) 0.3992(19) 0.5131(12) 0.043 Uiso d . 1 . . H
    H52 -0.1182(19) 0.267(2) 0.5217(12) 0.043 Uiso d . 1 . . H
    C6 -0.18483(19) 0.3401(2) 0.63616(13) 0.0303(5) Uani d . 1 . . C
    H61 -0.2762(18) 0.2948(16) 0.6352(12) 0.036 Uiso d . 1 . . H
    H62 -0.1920(19) 0.4185(19) 0.6655(12) 0.036 Uiso d . 1 . . H
    C7 0.12812(18) 0.19953(19) 0.75059(11) 0.0265(4) Uani d . 1 . . C
    O7 0.10466(13) 0.08763(13) 0.73431(8) 0.0373(4) Uani d . 1 . . O
    N8 0.22762(16) 0.24068(15) 0.80354(10) 0.0279(4) Uani d . 1 . . N
    H8N 0.2255(19) 0.3171(18) 0.8185(12) 0.033 Uiso d . 1 . . H
    C9 0.32758(17) 0.15887(17) 0.84329(11) 0.0264(5) Uani d . 1 . . C
    C10 0.42577(18) 0.10045(19) 0.79009(12) 0.0303(5) Uani d . 1 . . C
    C11 0.52297(19) 0.0242(2) 0.83062(14) 0.0362(5) Uani d . 1 . . C
    H11 0.5883(19) -0.0202(18) 0.7963(12) 0.043 Uiso d . 1 . . H
    C12 0.52420(19) 0.0087(2) 0.92023(13) 0.0385(5) Uani d . 1 . . C
    H12 0.596(2) -0.0410(18) 0.9486(13) 0.046 Uiso d . 1 . . H
    C13 0.4263(2) 0.06752(19) 0.97126(14) 0.0361(5) Uani d . 1 . . C
    H13 0.4241(19) 0.0596(18) 1.0312(14) 0.043 Uiso d . 1 . . H
    C14 0.32559(17) 0.14369(18) 0.93404(12) 0.0287(5) Uani d . 1 . . C
    C15 0.2167(3) 0.2058(2) 0.98935(14) 0.0413(5) Uani d . 1 . . C
    H81 0.122(2) 0.193(2) 0.9667(14) 0.062 Uiso d . 1 . . H
    H82 0.234(2) 0.296(2) 0.9926(13) 0.062 Uiso d . 1 . . H
    H83 0.215(2) 0.171(2) 1.0457(15) 0.062 Uiso d . 1 . . H
    C16 0.4275(2) 0.1189(3) 0.69241(14) 0.0453(6) Uani d . 1 . . C
    H91 0.520(2) 0.089(2) 0.6653(14) 0.068 Uiso d . 1 . . H
    H92 0.420(2) 0.210(2) 0.6766(14) 0.068 Uiso d . 1 . . H
    H93 0.359(2) 0.075(2) 0.6671(14) 0.068 Uiso d . 1 . . H
_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
    N1 C1' . 1.494(2) y
    N1 C2 . 1.495(2) y
    N1 C6 . 1.508(2) y
    N1 H1N . 0.905(17) no
    C1' H71 . 0.99(2) no
    C1' H72 . 0.99(2) no
    C1' H73 . 0.95(2) no
    C2 C7 . 1.526(2) y
    C2 C3 . 1.528(3) y
    C2 H2 . 0.932(18) no
    C3 C4 . 1.523(3) y
    C3 H31 . 0.99(2) no
    C3 H32 . 0.97(2) no
    C4 C5 . 1.512(3) y
    C4 H41 . 0.96(2) no
    C4 H42 . 0.96(2) no
    C5 C6 . 1.499(3) y
    C5 H51 . 0.95(2) no
    C5 H52 . 0.98(2) no
    C6 H61 . 1.011(17) no
    C6 H62 . 0.946(19) no
    C7 O7 . 1.231(2) y
    C7 N8 . 1.335(2) y
    N8 C9 . 1.437(2) y
    N8 H8N . 0.841(18) no
    C9 C14 . 1.396(2) y
    C9 C10 . 1.399(2) y
    C10 C11 . 1.389(3) y
    C10 C16 . 1.505(3) y
    C11 C12 . 1.379(3) y
    C11 H11 . 0.949(19) no
    C12 C13 . 1.380(3) y
    C12 H12 . 0.979(19) no
    C13 C14 . 1.391(2) y
    C13 H13 . 0.92(2) no
    C14 C15 . 1.507(3) y
    C15 H81 . 0.99(2) no
    C15 H82 . 0.97(3) no
    C15 H83 . 0.94(2) no
    C16 H91 . 1.04(2) no
    C16 H92 . 1.00(2) no
    C16 H93 . 0.90(2) no
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
    C1' N1 C2 . . 110.85(14) no
    C1' N1 C6 . . 109.49(15) no
    C2 N1 C6 . . 113.57(14) no
    C1' N1 H1N . . 106.4(11) no
    C2 N1 H1N . . 110.5(12) no
    C6 N1 H1N . . 105.7(11) no
    N1 C1' H71 . . 109.6(12) no
    N1 C1' H72 . . 106.1(12) no
    H71 C1' H72 . . 105.1(17) no
    N1 C1' H73 . . 109.6(14) no
    H71 C1' H73 . . 113.1(18) no
    H72 C1' H73 . . 113.0(18) no
    N1 C2 C7 . . 108.11(15) no
    N1 C2 C3 . . 111.13(15) no
    C7 C2 C3 . . 107.80(15) no
    N1 C2 H2 . . 107.5(11) no
    C7 C2 H2 . . 112.5(11) no
    C3 C2 H2 . . 109.9(11) no
    C4 C3 C2 . . 112.37(17) no
    C4 C3 H31 . . 109.6(12) no
    C2 C3 H31 . . 107.4(11) no
    C4 C3 H32 . . 109.9(11) no
    C2 C3 H32 . . 105.6(12) no
    H31 C3 H32 . . 111.9(16) no
    C5 C4 C3 . . 108.69(18) no
    C5 C4 H41 . . 111.6(12) no
    C3 C4 H41 . . 108.4(13) no
    C5 C4 H42 . . 111.0(12) no
    C3 C4 H42 . . 109.6(12) no
    H41 C4 H42 . . 107.6(19) no
    C6 C5 C4 . . 110.95(18) no
    C6 C5 H51 . . 105.8(12) no
    C4 C5 H51 . . 115.6(12) no
    C6 C5 H52 . . 106.9(11) no
    C4 C5 H52 . . 112.1(11) no
    H51 C5 H52 . . 104.8(17) no
    C5 C6 N1 . . 111.67(15) no
    C5 C6 H61 . . 113.8(10) no
    N1 C6 H61 . . 103.3(10) no
    C5 C6 H62 . . 112.5(11) no
    N1 C6 H62 . . 103.8(11) no
    H61 C6 H62 . . 110.9(16) no
    O7 C7 N8 . . 124.79(17) no
    O7 C7 C2 . . 119.88(16) no
    N8 C7 C2 . . 115.19(17) no
    C7 N8 C9 . . 123.45(16) no
    C7 N8 H8N . . 117.4(13) no
    C9 N8 H8N . . 118.7(13) no
    C14 C9 C10 . . 122.40(17) no
    C14 C9 N8 . . 118.66(16) no
    C10 C9 N8 . . 118.92(16) no
    C11 C10 C9 . . 117.60(18) no
    C11 C10 C16 . . 120.63(18) no
    C9 C10 C16 . . 121.77(18) no
    C12 C11 C10 . . 121.2(2) no
    C12 C11 H11 . . 118.9(11) no
    C10 C11 H11 . . 119.8(11) no
    C11 C12 C13 . . 120.1(2) no
    C11 C12 H12 . . 120.7(12) no
    C13 C12 H12 . . 119.2(11) no
    C12 C13 C14 . . 121.2(2) no
    C12 C13 H13 . . 122.6(12) no
    C14 C13 H13 . . 116.3(12) no
    C13 C14 C9 . . 117.56(18) no
    C13 C14 C15 . . 121.32(17) no
    C9 C14 C15 . . 121.10(18) no
    C14 C15 H81 . . 113.4(13) no
    C14 C15 H82 . . 109.5(13) no
    H81 C15 H82 . . 108.5(19) no
    C14 C15 H83 . . 111.0(13) no
    H81 C15 H83 . . 104.2(18) no
    H82 C15 H83 . . 110.1(19) no
    C10 C16 H91 . . 111.5(12) no
    C10 C16 H92 . . 111.4(13) no
    H91 C16 H92 . . 105.2(17) no
    C10 C16 H93 . . 110.6(15) no
    H91 C16 H93 . . 108.6(19) no
    H92 C16 H93 . . 109(2) no
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
    C1' N1 C2 C7 . . . . 68.55(19) ?
    C6 N1 C2 C7 . . . . -167.68(15) ?
    C1' N1 C2 C3 . . . . -173.34(18) ?
    C6 N1 C2 C3 . . . . -49.6(2) ?
    N1 C2 C3 C4 . . . . 52.7(2) ?
    C7 C2 C3 C4 . . . . 170.97(17) ?
    C2 C3 C4 C5 . . . . -57.3(3) ?
    C3 C4 C5 C6 . . . . 59.2(2) ?
    C4 C5 C6 N1 . . . . -57.2(2) ?
    C1' N1 C6 C5 . . . . 176.99(17) ?
    C2 N1 C6 C5 . . . . 52.5(2) ?
    N1 C2 C7 O7 . . . . 39.7(2) ?
    C3 C2 C7 O7 . . . . -80.5(2) ?
    N1 C2 C7 N8 . . . . -144.20(15) ?
    C3 C2 C7 N8 . . . . 95.59(19) ?
    O7 C7 N8 C9 . . . . 5.0(3) ?
    C2 C7 N8 C9 . . . . -170.83(15) ?
    C7 N8 C9 C14 . . . . -113.3(2) ?
    C7 N8 C9 C10 . . . . 68.6(2) ?
    C14 C9 C10 C11 . . . . 0.5(3) ?
    N8 C9 C10 C11 . . . . 178.55(17) ?
    C14 C9 C10 C16 . . . . -179.3(2) ?
    N8 C9 C10 C16 . . . . -1.3(3) ?
    C9 C10 C11 C12 . . . . -1.2(3) ?
    C16 C10 C11 C12 . . . . 178.7(2) ?
    C10 C11 C12 C13 . . . . 1.1(3) ?
    C11 C12 C13 C14 . . . . -0.3(3) ?
    C12 C13 C14 C9 . . . . -0.3(3) ?
    C12 C13 C14 C15 . . . . 178.7(2) ?
    C10 C9 C14 C13 . . . . 0.2(3) ?
    N8 C9 C14 C13 . . . . -177.81(16) ?
    C10 C9 C14 C15 . . . . -178.77(18) ?
    N8 C9 C14 C15 . . . . 3.2(3) ?
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 H1N Cl 3_546 0.905(17) 2.182(18) 3.0140(16) 152.5(16) y
    N8 H8N Cl . 0.841(18) 2.280(19) 3.1172(17) 174.1(17) y
