#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226717.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2226717
loop_
_publ_author_name
'Schutte, Marietjie'
'Visser, Hendrik G.'
'Roodt, Andreas'
_publ_section_title
;
 Tetraethylammonium bromidotricarbonyl(tropolonato)rhenate(I)
;
_journal_coeditor_code           WM2362
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m859
_journal_page_last               m860
_journal_paper_doi               10.1107/S1600536810024505
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C8 H20 N) [Re Br (C7 H5 O2) (C O)3]'
_chemical_formula_moiety         'C8 H20 N +, C10 H5 Br O5 Re -'
_chemical_formula_sum            'C18 H25 Br N O5 Re'
_chemical_formula_weight         601.5
_chemical_name_systematic
;
Tetraethylammonium bromidotricarbonyl(tropolonato)rhenate(I)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00
_cell_angle_beta                 101.983(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.334(5)
_cell_length_b                   10.754(5)
_cell_length_c                   16.053(5)
_cell_measurement_reflns_used    9467
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.3
_cell_volume                     2082.9(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16808
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.9
_exptl_absorpt_coefficient_mu    7.779
_exptl_absorpt_correction_T_max  0.273
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.167
_refine_diff_density_max         3.159
_refine_diff_density_min         -1.413
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.13
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         5160
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.13
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0337P)²+6.0941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0862
_reflns_number_gt                4700
_reflns_number_total             5160
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            wm2362.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226717
_cod_database_fobs_code          2226717
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'
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
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'
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_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_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
