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###                                                                        ###
###        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/  #
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# This file may be used for bona fide research purposes within the           #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(3,4-dihydroxyphenyl)ethanaminium perchlorate
;
_chemical_name_common     'Dopaminium perchlorate'
_chemical_formula_moiety     'C8 H12 N O2 +, Cl O4 -'
_chemical_formula_sum     'C8 H12 Cl N O6'
_chemical_formula_iupac     'C8 H12 N O2 +, Cl O4 -'
_chemical_formula_weight     253.64
_chemical_melting_point     ?
_symmetry_cell_setting     Triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_hall     -P1
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     7.4925(3)
_cell_length_b     8.2254(3)
_cell_length_c     8.9524(4)
_cell_angle_alpha     106.9100(10)
_cell_angle_beta     94.1860(10)
_cell_angle_gamma     101.2060(10)
_cell_volume     512.85(4)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     3633
_cell_measurement_theta_min     2.40
_cell_measurement_theta_max     31.59
_cell_measurement_temperature     150(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.06
_exptl_crystal_density_diffrn     1.642
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     264
_exptl_absorpt_coefficient_mu     0.387
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.8928
_exptl_absorpt_correction_T_max     0.9772
_exptl_special_details
;
;
_diffrn_ambient_temperature     150(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 APEXII CCD'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6199
_diffrn_reflns_av_R_equivalents     0.0178
_diffrn_reflns_av_sigmaI/netI     0.0233
_diffrn_reflns_theta_min     2.40
_diffrn_reflns_theta_max     31.71
_diffrn_reflns_theta_full     26.00
_diffrn_measured_fraction_theta_max     0.908
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_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 > σ(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     3146
_reflns_number_gt     2858
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0397
_refine_ls_R_factor_gt     0.0360
_refine_ls_wR_factor_gt     0.1018
_refine_ls_wR_factor_ref     0.1048
_refine_ls_goodness_of_fit_ref     1.085
_refine_ls_restrained_S_all     1.085
_refine_ls_number_reflns     3146
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0559P)²+0.2163P] 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     0.490
_refine_diff_density_min     -0.454
_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'
    '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'
_computing_data_collection     'APEX2 (Bruker, 2005)'
_computing_cell_refinement     'SAINT (Bruker, 2005)'
_computing_data_reduction     'SAINT (Bruker, 2005)'
_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
    Cl Cl1 0.78299(4) 0.71277(4) 0.38696(3) 0.01882(9) Uani d . 1 . .
    O O11 0.78911(17) 0.88541(14) 0.49463(13) 0.0299(2) Uani d . 1 . .
    O O12 0.61768(16) 0.59722(16) 0.39753(16) 0.0370(3) Uani d . 1 . .
    O O13 0.7897(2) 0.7193(2) 0.23036(14) 0.0436(3) Uani d . 1 . .
    O O14 0.93581(16) 0.65238(18) 0.43983(14) 0.0373(3) Uani d . 1 . .
    C C1 0.28726(18) 0.78530(16) 1.02178(15) 0.0185(2) Uani d . 1 . .
    C C2 0.45074(18) 0.77363(16) 0.95805(14) 0.0185(2) Uani d . 1 . .
    H H2 0.5479 0.7464 1.0135 0.022 Uiso calc R 1 . .
    C C3 0.47193(17) 0.80155(16) 0.81453(14) 0.0177(2) Uani d . 1 . .
    O O1 0.63545(13) 0.79282(13) 0.75554(11) 0.02136(19) Uani d . 1 . .
    C C4 0.32907(18) 0.84083(16) 0.73205(14) 0.0188(2) Uani d . 1 . .
    O O2 0.36279(15) 0.86353(13) 0.58877(11) 0.0240(2) Uani d . 1 . .
    C C5 0.16751(18) 0.85522(17) 0.79484(16) 0.0212(2) Uani d . 1 . .
    H H5 0.0713 0.8842 0.7397 0.025 Uiso calc R 1 . .
    C C6 0.14636(18) 0.82696(17) 0.93990(16) 0.0208(2) Uani d . 1 . .
    H H6 0.0352 0.8362 0.9829 0.025 Uiso calc R 1 . .
    C C7 0.2661(2) 0.75345(17) 1.17802(15) 0.0215(2) Uani d . 1 . .
    H H7A 0.1522 0.7850 1.2147 0.026 Uiso calc R 1 . .
    H H7B 0.3713 0.8279 1.2575 0.026 Uiso calc R 1 . .
    C C8 0.2576(2) 0.56300(17) 1.16162(15) 0.0222(3) Uani d . 1 . .
    H H8A 0.1526 0.4892 1.0815 0.027 Uiso calc R 1 . .
    H H8B 0.3714 0.5320 1.1244 0.027 Uiso calc R 1 . .
    N N1 0.23650(15) 0.52615(15) 1.31419(13) 0.0200(2) Uani d . 1 . .
    H H1A 0.2317 0.4112 1.2999 0.030 Uiso calc R 1 . .
    H H1B 0.1310 0.5528 1.3479 0.030 Uiso calc R 1 . .
    H H1C 0.3340 0.5921 1.3875 0.030 Uiso calc R 1 . .
    H H2O 0.2968 0.9273 0.5626 0.040 Uiso d . 1 . .
    H H1O 0.6356 0.8281 0.6748 0.040 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
    Cl1 0.01669(14) 0.02486(16) 0.01828(15) 0.00806(11) 0.00411(10) 0.00922(11)
    O11 0.0394(6) 0.0222(5) 0.0305(5) 0.0104(4) 0.0048(4) 0.0096(4)
    O12 0.0253(5) 0.0348(6) 0.0453(7) -0.0014(5) 0.0097(5) 0.0083(5)
    O13 0.0561(8) 0.0597(8) 0.0200(5) 0.0123(7) 0.0065(5) 0.0201(5)
    O14 0.0303(6) 0.0537(7) 0.0342(6) 0.0287(5) 0.0029(4) 0.0113(5)
    C1 0.0249(6) 0.0149(5) 0.0170(5) 0.0059(4) 0.0049(4) 0.0058(4)
    C2 0.0241(6) 0.0173(5) 0.0166(5) 0.0079(4) 0.0028(4) 0.0070(4)
    C3 0.0224(5) 0.0153(5) 0.0168(5) 0.0066(4) 0.0046(4) 0.0052(4)
    O1 0.0248(5) 0.0250(5) 0.0206(4) 0.0118(4) 0.0087(3) 0.0114(4)
    C4 0.0256(6) 0.0168(5) 0.0150(5) 0.0061(4) 0.0016(4) 0.0059(4)
    O2 0.0327(5) 0.0276(5) 0.0174(4) 0.0132(4) 0.0047(4) 0.0116(4)
    C5 0.0229(6) 0.0209(5) 0.0213(6) 0.0070(5) 0.0005(4) 0.0079(5)
    C6 0.0215(6) 0.0199(5) 0.0229(6) 0.0063(4) 0.0052(5) 0.0079(5)
    C7 0.0301(6) 0.0193(5) 0.0194(6) 0.0091(5) 0.0094(5) 0.0085(4)
    C8 0.0331(7) 0.0189(5) 0.0168(5) 0.0077(5) 0.0048(5) 0.0077(4)
    N1 0.0215(5) 0.0229(5) 0.0208(5) 0.0085(4) 0.0064(4) 0.0118(4)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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
    Cl1 O13 . 1.4225(11) ?
    Cl1 O12 . 1.4347(11) ?
    Cl1 O14 . 1.4355(11) ?
    Cl1 O11 . 1.4559(11) ?
    C1 C6 . 1.3939(18) ?
    C1 C2 . 1.3968(18) ?
    C1 C7 . 1.5099(17) ?
    C2 C3 . 1.3842(16) ?
    C2 H2 . 0.9500 ?
    C3 O1 . 1.3753(15) ?
    C3 C4 . 1.3975(18) ?
    O1 H1O . 0.8537 ?
    C4 C5 . 1.3826(19) ?
    C4 O2 . 1.3828(15) ?
    O2 H2O . 0.8540 ?
    C5 C6 . 1.3989(18) ?
    C5 H5 . 0.9500 ?
    C6 H6 . 0.9500 ?
    C7 C8 . 1.5185(18) ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C8 N1 . 1.4954(16) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    N1 H1A . 0.9100 ?
    N1 H1B . 0.9100 ?
    N1 H1C . 0.9100 ?
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
    O13 Cl1 O12 . . 111.25(8) ?
    O13 Cl1 O14 . . 111.08(8) ?
    O12 Cl1 O14 . . 107.81(8) ?
    O13 Cl1 O11 . . 110.40(8) ?
    O12 Cl1 O11 . . 108.15(7) ?
    O14 Cl1 O11 . . 108.02(7) ?
    C6 C1 C2 . . 119.24(11) ?
    C6 C1 C7 . . 121.09(11) ?
    C2 C1 C7 . . 119.67(11) ?
    C3 C2 C1 . . 120.37(12) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    O1 C3 C2 . . 119.37(11) ?
    O1 C3 C4 . . 120.57(11) ?
    C2 C3 C4 . . 120.06(11) ?
    C3 O1 H1O . . 109.3 ?
    C5 C4 O2 . . 124.27(11) ?
    C5 C4 C3 . . 120.16(11) ?
    O2 C4 C3 . . 115.56(11) ?
    C4 O2 H2O . . 111.4 ?
    C4 C5 C6 . . 119.69(12) ?
    C4 C5 H5 . . 120.2 ?
    C6 C5 H5 . . 120.2 ?
    C1 C6 C5 . . 120.47(12) ?
    C1 C6 H6 . . 119.8 ?
    C5 C6 H6 . . 119.8 ?
    C1 C7 C8 . . 110.27(10) ?
    C1 C7 H7A . . 109.6 ?
    C8 C7 H7A . . 109.6 ?
    C1 C7 H7B . . 109.6 ?
    C8 C7 H7B . . 109.6 ?
    H7A C7 H7B . . 108.1 ?
    N1 C8 C7 . . 111.89(10) ?
    N1 C8 H8A . . 109.2 ?
    C7 C8 H8A . . 109.2 ?
    N1 C8 H8B . . 109.2 ?
    C7 C8 H8B . . 109.2 ?
    H8A C8 H8B . . 107.9 ?
    C8 N1 H1A . . 109.5 ?
    C8 N1 H1B . . 109.5 ?
    H1A N1 H1B . . 109.5 ?
    C8 N1 H1C . . 109.5 ?
    H1A N1 H1C . . 109.5 ?
    H1B N1 H1C . . 109.5 ?
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
    O1 H1O O11 . 0.85 2.16 2.9065(14) 146
    O2 H2O O11 2_676 0.85 1.96 2.7936(15) 164
    N1 H1A O1 2_667 0.91 2.07 2.8822(14) 148
    N1 H1B O14 1_456 0.91 1.93 2.8317(16) 169
    N1 H1C O12 1_556 0.91 2.11 2.8002(16) 132
    N1 H1C O2 1_556 0.91 2.39 3.0512(16) 130
data_global
_journal_date_recd_electronic     2008-10-20
_journal_date_accepted     2008-10-30
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue     12
_journal_page_first     o2268
_journal_page_last     o2268
_journal_paper_category     QO
_journal_coeditor_code     CV2470
_publ_contact_author_name     'Davar M. Boghaei'
_publ_contact_author_address
;
Department of Chemistry,
Sharif University of Technology,
P. O. Box 11155-8639,
Tehran, Iran
;
_publ_contact_author_email     dboghaei@sharif.edu
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
Dopaminium perchlorate
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Boghaei, Davar M.' .
;
Department of Chemistry, Sharif University of Technology, PO Box 11155-8639,
Tehran, Iran
;
    'Baniyaghoob, Sahar' .
;
Department of Chemistry, Sharif University of Technology, PO Box 11155-8639,
Tehran, Iran
;
    'Najafpour, Mohammad Mahdi' .
;
Department of Chemistry, Sharif University of Technology, PO Box 11155-8639,
Tehran, Iran
;
    'McKee, Vickie' .
;
Department of Chemistry,
Loughborough University,
Leicestershire LE11 3TU,
England
;
