##############################################################################
###                                                                        ###
###        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_global
_audit_creation_method     'WinGX routine CIF_UPDATE'
_audit_conform_dict_name     cif_core.dic
_audit_conform_dict_version     2.4
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-06-08
_journal_date_accepted     2010-06-23
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      7
_journal_page_first     m859
_journal_page_last     m860
_journal_paper_category     QM
_journal_coeditor_code     WM2362
_publ_contact_author_name     'Schutte, M'
_publ_contact_author_address
;
Department of Chemistry
University of the Free State
P.O. Box 339
Bloemfontein
9300
South Africa
;
_publ_contact_author_email     schuttem@ufs.ac.za
_publ_contact_author_fax     '+27 51 444 6384'
_publ_contact_author_phone     '+27 51 401 7035'
_publ_section_title
;
Tetraethylammonium bromidotricarbonyl(tropolonato)rhenate(I)
;
loop_
    _publ_author_name
    _publ_author_address
    'Schutte, Marietjie'
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein
9300
South Africa
;
    'Visser, Hendrik G'
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein
9300
South Africa
;
    'Roodt, Andreas'
;
Department of Chemistry
University of the Free State
PO Box 339
Bloemfontein
9300
South Africa
;
data_I
_audit_creation_method     'WinGX routine CIF_UPDATE'
_chemical_name_systematic
;
Tetraethylammonium bromidotricarbonyl(tropolonato)rhenate(I)
;
_chemical_formula_moiety     'C8 H20 N +, C10 H5 Br O5 Re -'
_chemical_formula_sum     'C18 H25 Br N O5 Re'
_chemical_formula_iupac     '(C8 H20 N) [Re Br (C7 H5 O2) (C O)3]'
_chemical_formula_weight     601.5
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x+1/2, y+1/2, -z+1/2'
    '-x, -y, -z'
    'x-1/2, -y-1/2, z-1/2'
_cell_length_a     12.334(5)
_cell_length_b     10.754(5)
_cell_length_c     16.053(5)
_cell_angle_alpha     90.00
_cell_angle_beta     101.983(5)
_cell_angle_gamma     90.00
_cell_volume     2082.9(14)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9467
_cell_measurement_theta_min     2.3
_cell_measurement_theta_max     28.26
_cell_measurement_temperature     100(2)
_exptl_crystal_description     cuboid
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.580
_exptl_crystal_size_mid     0.184
_exptl_crystal_size_min     0.167
_exptl_crystal_density_diffrn     1.918
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1160
_exptl_absorpt_coefficient_mu     7.779
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.196
_exptl_absorpt_correction_T_max     0.273
_exptl_special_details
;
;
_diffrn_ambient_temperature     100(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART CCD'
_diffrn_measurement_method     'phi and omega scans'
_diffrn_reflns_number     16808
_diffrn_reflns_av_R_equivalents     0.0465
_diffrn_reflns_theta_min     1.9
_diffrn_reflns_theta_max     28.31
_diffrn_reflns_theta_full     28.31
_diffrn_measured_fraction_theta_max     0.995
_diffrn_measured_fraction_theta_full     0.995
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     12
_diffrn_reflns_limit_l_min     -21
_diffrn_reflns_limit_l_max     21
_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 >
2σ(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     5160
_reflns_number_gt     4700
_reflns_threshold_expression     >2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0387
_refine_ls_R_factor_gt     0.0343
_refine_ls_wR_factor_ref     0.0862
_refine_ls_goodness_of_fit_ref     1.13
_refine_ls_restrained_S_all     1.13
_refine_ls_number_reflns     5160
_refine_ls_number_parameters     251
_refine_ls_number_restraints     3
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0337P)²+6.0941P] 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     0.002
_refine_ls_shift/su_mean     0
_refine_diff_density_max     3.159
_refine_diff_density_min     -1.413
_refine_ls_extinction_method     none
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    Re Re -1.0185 7.231 '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, 2005)'
_computing_cell_refinement     'SAINT-Plus (Bruker, 2004)'
_computing_data_reduction     'SAINT-Plus (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material     'WinGX (Farrugia, 1999)'
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 0.8439(4) 0.5302(5) 0.5663(3) 0.0181(9) Uani d . 1 A .
    C C2 0.9102(4) 0.7076(5) 0.4752(3) 0.0199(10) Uani d . 1 A .
    C C11 0.5498(4) 0.5523(4) 0.3763(3) 0.0148(9) Uani d . 1 . .
    C C12 0.5849(4) 0.6462(4) 0.3215(3) 0.0149(9) Uani d . 1 . .
    C C13 0.5209(4) 0.6930(5) 0.2455(3) 0.0197(10) Uani d . 1 . .
    H H13 0.5552 0.7546 0.2196 0.024 Uiso calc R 1 . .
    C C14 0.4145(4) 0.6621(6) 0.2027(3) 0.0274(12) Uani d . 1 . .
    H H14 0.3896 0.7047 0.152 0.033 Uiso calc R 1 . .
    C C15 0.3397(4) 0.5777(6) 0.2239(3) 0.0310(13) Uani d . 1 . .
    H H15 0.2724 0.5697 0.1854 0.037 Uiso calc R 1 . .
    C C16 0.3543(4) 0.5036(6) 0.2965(3) 0.0247(11) Uani d . 1 . .
    H H16 0.2949 0.4524 0.3006 0.03 Uiso calc R 1 . .
    C C17 0.4455(4) 0.4958(5) 0.3636(3) 0.0205(10) Uani d . 1 . .
    H H17 0.4355 0.444 0.4077 0.025 Uiso calc R 1 . .
    C C21 0.5919(4) 0.0054(5) 0.3394(3) 0.0208(10) Uani d . 1 . .
    H H21A 0.6032 -0.0001 0.2814 0.025 Uiso calc R 1 . .
    H H21B 0.6263 -0.0671 0.3698 0.025 Uiso calc R 1 . .
    C C22 0.4687(4) 0.0006(6) 0.3370(3) 0.0253(11) Uani d . 1 . .
    H H22A 0.4331 0.0706 0.3056 0.038 Uiso calc R 1 . .
    H H22B 0.4563 0.003 0.394 0.038 Uiso calc R 1 . .
    H H22C 0.4385 -0.075 0.3098 0.038 Uiso calc R 1 . .
    C C23 0.7703(4) 0.1180(5) 0.3677(3) 0.0212(10) Uani d . 1 . .
    H H23A 0.7689 0.1153 0.3071 0.025 Uiso calc R 1 . .
    H H23B 0.8066 0.1947 0.3898 0.025 Uiso calc R 1 . .
    C C24 0.8381(5) 0.0097(6) 0.4099(4) 0.0290(12) Uani d . 1 . .
    H H24A 0.8041 -0.0668 0.3872 0.044 Uiso calc R 1 . .
    H H24B 0.8416 0.0125 0.4702 0.044 Uiso calc R 1 . .
    H H24C 0.9117 0.0146 0.3991 0.044 Uiso calc R 1 . .
    C C25 0.6461(4) 0.1209(5) 0.4744(3) 0.0208(10) Uani d . 1 . .
    H H25A 0.673 0.0413 0.4987 0.025 Uiso calc R 1 . .
    H H25B 0.5693 0.1285 0.479 0.025 Uiso calc R 1 . .
    C C26 0.7123(5) 0.2234(6) 0.5273(3) 0.0303(12) Uani d . 1 . .
    H H26A 0.789 0.2158 0.5247 0.045 Uiso calc R 1 . .
    H H26B 0.7045 0.2161 0.5854 0.045 Uiso calc R 1 . .
    H H26C 0.685 0.303 0.5052 0.045 Uiso calc R 1 . .
    C C27 0.5946(4) 0.2388(5) 0.3406(3) 0.0218(10) Uani d . 1 . .
    H H27A 0.5218 0.2442 0.3544 0.026 Uiso calc R 1 . .
    H H27B 0.6373 0.3097 0.3664 0.026 Uiso calc R 1 . .
    C C28 0.5810(5) 0.2483(5) 0.2445(3) 0.0261(11) Uani d . 1 . .
    H H28A 0.5453 0.3254 0.2251 0.039 Uiso calc R 1 . .
    H H28B 0.5366 0.1802 0.2178 0.039 Uiso calc R 1 . .
    H H28C 0.6525 0.2452 0.2298 0.039 Uiso calc R 1 . .
    N N1 0.6509(3) 0.1205(4) 0.3806(3) 0.0175(8) Uani d . 1 . .
    O O1 0.8829(3) 0.4790(4) 0.6285(2) 0.0295(9) Uani d . 1 . .
    O O2 0.9905(3) 0.7658(4) 0.4826(2) 0.0278(8) Uani d . 1 . .
    O O11 0.6230(3) 0.5185(3) 0.44163(19) 0.0156(6) Uani d . 1 A .
    O O12 0.6850(3) 0.6885(3) 0.34718(19) 0.0158(6) Uani d . 1 A .
    Re Re1 0.778478(14) 0.611175(17) 0.462429(10) 0.01392(7) Uani d D 1 . .
    Br Br1A 0.66965(4) 0.77746(5) 0.53345(3) 0.01591(18) Uani d P 0.922(3) A 1
    C C3A 0.8454(5) 0.4916(7) 0.4061(4) 0.0190(12) Uani d P 0.922(3) A 1
    O O3A 0.8876(5) 0.4139(5) 0.3694(3) 0.0257(10) Uani d P 0.922(3) A 1
    Br Br1B 0.8340(11) 0.4525(12) 0.3685(8) 0.043(3) Uani d P 0.078(3) A 2
    C C3B 0.718(5) 0.741(4) 0.522(3) 0.0190(12) Uani d PD 0.078(3) A 2
    O O3B 0.679(5) 0.816(4) 0.554(4) 0.0257(10) Uani d PD 0.078(3) A 2
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    C1 O1 . 1.153(6) ?
    C1 Re1 . 1.906(5) y
    C2 O2 . 1.156(6) ?
    C2 Re1 . 1.903(5) y
    C11 O11 . 1.286(5) ?
    C11 C17 . 1.398(7) ?
    C11 C12 . 1.462(6) ?
    C12 O12 . 1.300(5) ?
    C12 C13 . 1.402(6) ?
    C13 C14 . 1.389(7) ?
    C13 H13 . 0.93 ?
    C14 C15 . 1.385(8) ?
    C14 H14 . 0.93 ?
    C15 C16 . 1.392(7) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.390(7) ?
    C16 H16 . 0.93 ?
    C17 H17 . 0.93 ?
    C21 C22 . 1.513(7) ?
    C21 N1 . 1.517(6) ?
    C21 H21A . 0.97 ?
    C21 H21B . 0.97 ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
    C23 C24 . 1.510(7) ?
    C23 N1 . 1.529(6) ?
    C23 H23A . 0.97 ?
    C23 H23B . 0.97 ?
    C24 H24A . 0.96 ?
    C24 H24B . 0.96 ?
    C24 H24C . 0.96 ?
    C25 N1 . 1.520(6) ?
    C25 C26 . 1.521(7) ?
    C25 H25A . 0.97 ?
    C25 H25B . 0.97 ?
    C26 H26A . 0.96 ?
    C26 H26B . 0.96 ?
    C26 H26C . 0.96 ?
    C27 C28 . 1.520(6) ?
    C27 N1 . 1.525(6) ?
    C27 H27A . 0.97 ?
    C27 H27B . 0.97 ?
    C28 H28A . 0.96 ?
    C28 H28B . 0.96 ?
    C28 H28C . 0.96 ?
    O11 Re1 . 2.126(3) y
    O12 Re1 . 2.135(3) y
    Re1 C3A . 1.861(7) y
    Re1 C3B . 1.923(18) y
    Re1 Br1B . 2.467(16) y
    Re1 Br1A . 2.6334(9) y
    C3A O3A . 1.201(9) ?
    C3B O3B . 1.123(18) ?
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
    O1 C1 Re1 . . 178.7(5) ?
    O2 C2 Re1 . . 179.5(5) ?
    O11 C11 C17 . . 117.7(4) ?
    O11 C11 C12 . . 116.1(4) ?
    C17 C11 C12 . . 126.2(4) ?
    O12 C12 C13 . . 118.4(4) ?
    O12 C12 C11 . . 115.6(4) ?
    C13 C12 C11 . . 126.0(4) ?
    C14 C13 C12 . . 130.4(5) ?
    C14 C13 H13 . . 114.8 ?
    C12 C13 H13 . . 114.8 ?
    C15 C14 C13 . . 130.1(5) ?
    C15 C14 H14 . . 114.9 ?
    C13 C14 H14 . . 114.9 ?
    C14 C15 C16 . . 127.1(5) ?
    C14 C15 H15 . . 116.5 ?
    C16 C15 H15 . . 116.5 ?
    C17 C16 C15 . . 128.8(5) ?
    C17 C16 H16 . . 115.6 ?
    C15 C16 H16 . . 115.6 ?
    C16 C17 C11 . . 131.3(5) ?
    C16 C17 H17 . . 114.4 ?
    C11 C17 H17 . . 114.4 ?
    C22 C21 N1 . . 115.3(4) ?
    C22 C21 H21A . . 108.4 ?
    N1 C21 H21A . . 108.4 ?
    C22 C21 H21B . . 108.4 ?
    N1 C21 H21B . . 108.4 ?
    H21A C21 H21B . . 107.5 ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C24 C23 N1 . . 114.4(4) ?
    C24 C23 H23A . . 108.7 ?
    N1 C23 H23A . . 108.7 ?
    C24 C23 H23B . . 108.7 ?
    N1 C23 H23B . . 108.7 ?
    H23A C23 H23B . . 107.6 ?
    C23 C24 H24A . . 109.5 ?
    C23 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C23 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    N1 C25 C26 . . 115.4(4) ?
    N1 C25 H25A . . 108.4 ?
    C26 C25 H25A . . 108.4 ?
    N1 C25 H25B . . 108.4 ?
    C26 C25 H25B . . 108.4 ?
    H25A C25 H25B . . 107.5 ?
    C25 C26 H26A . . 109.5 ?
    C25 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C25 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C28 C27 N1 . . 115.3(4) ?
    C28 C27 H27A . . 108.4 ?
    N1 C27 H27A . . 108.4 ?
    C28 C27 H27B . . 108.4 ?
    N1 C27 H27B . . 108.4 ?
    H27A C27 H27B . . 107.5 ?
    C27 C28 H28A . . 109.5 ?
    C27 C28 H28B . . 109.5 ?
    H28A C28 H28B . . 109.5 ?
    C27 C28 H28C . . 109.5 ?
    H28A C28 H28C . . 109.5 ?
    H28B C28 H28C . . 109.5 ?
    C21 N1 C25 . . 108.7(4) ?
    C21 N1 C27 . . 111.2(4) ?
    C25 N1 C27 . . 107.9(4) ?
    C21 N1 C23 . . 108.3(4) ?
    C25 N1 C23 . . 111.8(4) ?
    C27 N1 C23 . . 109.0(4) ?
    C11 O11 Re1 . . 116.9(3) ?
    C12 O12 Re1 . . 116.4(3) ?
    C3A Re1 C2 . . 88.5(2) ?
    C3A Re1 C1 . . 87.7(2) ?
    C2 Re1 C1 . . 87.6(2) ?
    C3A Re1 C3B . . 176(2) ?
    C2 Re1 C3B . . 88(2) ?
    C1 Re1 C3B . . 92.1(19) ?
    C3A Re1 O11 . . 94.4(2) ?
    C2 Re1 O11 . . 174.40(17) ?
    C1 Re1 O11 . . 97.33(17) ?
    C3B Re1 O11 . . 89(2) ?
    C3A Re1 O12 . . 93.6(2) ?
    C2 Re1 O12 . . 100.19(16) ?
    C1 Re1 O12 . . 172.18(16) ?
    C3B Re1 O12 . . 87.1(18) ?
    O11 Re1 O12 . . 74.88(12) ?
    C3A Re1 Br1B . . 10.7(4) ?
    C2 Re1 Br1B . . 96.0(3) ?
    C1 Re1 Br1B . . 95.6(3) ?
    C3B Re1 Br1B . . 171.5(19) ?
    O11 Re1 Br1B . . 86.3(3) ?
    O12 Re1 Br1B . . 84.8(3) ?
    C3A Re1 Br1A . . 175.61(19) ?
    C2 Re1 Br1A . . 94.80(15) ?
    C1 Re1 Br1A . . 95.34(14) ?
    C3B Re1 Br1A . . 7.5(19) ?
    O11 Re1 Br1A . . 82.07(9) ?
    O12 Re1 Br1A . . 83.01(9) ?
    Br1B Re1 Br1A . . 165.0(3) ?
    O3A C3A Re1 . . 179.3(6) ?
    O3B C3B Re1 . . 177(6) ?
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
    C13 H13 O3A 2_655 0.93 2.43 3.344(7) 169
    C25 H25A Br1A 1_545 0.97 2.89 3.809(5) 157.7
    C26 H26C O11 . 0.96 2.58 3.542(7) 176.2
    C27 H27B O11 . 0.97 2.57 3.401(6) 143.4
