#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227047.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_2227047
loop_
_publ_author_name
'Suthiram, Janine'
'Zeevaart, Jan Rijn'
'Visser, Hendrik G.'
'Roodt, Andreas'
_publ_section_title
;
 Tetraethylammonium
 tricarbonylchlorido(quinoxaline-2-carboxylato-κ²N¹,O)rhenate(I)
;
_journal_coeditor_code           PV2307
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1042
_journal_page_last               m1043
_journal_paper_doi               10.1107/S160053681002893X
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '(C8 H20 N) [Re (C9 H5 N2 O2) Cl (C O)3]'
_chemical_formula_moiety         'C8 H20 N +, C12 H5 Cl N2 O5 Re -'
_chemical_formula_sum            'C20 H25 Cl N3 O5 Re'
_chemical_formula_weight         609.0808
_chemical_name_systematic
;
Tetraethylammonium tricarbonylchlorido(quinoxaline-2-
carboxylato-κ²N¹,O)rhenate(I)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                97.433(5)
_cell_angle_beta                 103.141(5)
_cell_angle_gamma                90.686(5)
_cell_formula_units_Z            2
_cell_length_a                   8.402(5)
_cell_length_b                   10.077(5)
_cell_length_c                   13.495(5)
_cell_measurement_reflns_used    9175
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.3
_cell_measurement_theta_min      2.73
_cell_volume                     1102.3(9)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2004)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type
;
Bruker X8 APEXII 4K Kappa CCD
;
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22501
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    5.669
_exptl_absorpt_correction_T_max  0.324
_exptl_absorpt_correction_T_min  0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.835
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Cuboid
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.286
_exptl_crystal_size_min          0.198
_refine_diff_density_max         1.744
_refine_diff_density_min         -1.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5458
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0211P)²+1.8438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0654
_reflns_number_gt                4988
_reflns_number_total             5458
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2307.cif
_cod_data_source_block           I
_cod_database_code               2227047
_cod_database_fobs_code          2227047
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Re Re1 0.528310(18) 0.255408(14) 0.783120(11) 0.01364(5) Uani d . 1 . .
Cl Cl1 0.81842(12) 0.20551(10) 0.85067(7) 0.0205(2) Uani d . 1 . .
O O3 0.1770(4) 0.3314(3) 0.6974(2) 0.0304(7) Uani d U 1 . .
C C3 0.3080(5) 0.3001(4) 0.7268(3) 0.0208(8) Uani d U 1 . .
N N3 0.0788(4) 0.7963(3) 0.8126(2) 0.0139(6) Uani d . 1 . .
O O1 0.4040(4) 0.1531(3) 0.9570(2) 0.0279(7) Uani d . 1 . .
O O4 0.5167(3) 0.0596(3) 0.6987(2) 0.0182(6) Uani d . 1 . .
N N1 0.6229(4) 0.2820(3) 0.6466(2) 0.0124(6) Uani d . 1 . .
O O2 0.5953(4) 0.5310(3) 0.9133(2) 0.0290(7) Uani d U 1 . .
C C2 0.5683(5) 0.4271(4) 0.8632(3) 0.0191(8) Uani d U 1 . .
C C13 -0.0041(5) 0.8729(4) 0.8902(3) 0.0162(8) Uani d . 1 . .
H H13A 0.0418 0.8469 0.9572 0.019 Uiso calc R 1 . .
H H13B 0.0218 0.9677 0.894 0.019 Uiso calc R 1 . .
C C15 0.0262(5) 0.6478(4) 0.7929(3) 0.0198(8) Uani d . 1 . .
H H15A -0.091 0.6396 0.7647 0.024 Uiso calc R 1 . .
H H15B 0.0784 0.6037 0.7411 0.024 Uiso calc R 1 . .
C C1 0.4532(5) 0.1938(4) 0.8923(3) 0.0195(8) Uani d . 1 . .
C C20 0.0905(5) 0.9922(4) 0.7091(3) 0.0236(9) Uani d . 1 . .
H H20A 0.0551 1.0511 0.7609 0.035 Uiso calc R 1 . .
H H20B 0.0466 1.0193 0.643 0.035 Uiso calc R 1 . .
H H20C 0.2078 0.9963 0.7229 0.035 Uiso calc R 1 . .
C C14 -0.1876(5) 0.8518(4) 0.8673(3) 0.0214(8) Uani d . 1 . .
H H14A -0.2342 0.8703 0.799 0.032 Uiso calc R 1 . .
H H14B -0.2305 0.911 0.9156 0.032 Uiso calc R 1 . .
H H14C -0.2148 0.7607 0.8729 0.032 Uiso calc R 1 . .
C C18 0.3657(5) 0.7536(5) 0.7873(4) 0.0311(10) Uani d . 1 . .
H H18A 0.3362 0.66 0.7679 0.047 Uiso calc R 1 . .
H H18B 0.4789 0.7645 0.8227 0.047 Uiso calc R 1 . .
H H18C 0.3486 0.7974 0.7269 0.047 Uiso calc R 1 . .
C C19 0.0298(5) 0.8491(4) 0.7098(3) 0.0160(8) Uani d . 1 . .
H H19A -0.0886 0.8444 0.6882 0.019 Uiso calc R 1 . .
H H19B 0.071 0.7903 0.6594 0.019 Uiso calc R 1 . .
C C16 0.0657(6) 0.5747(4) 0.8857(4) 0.0296(10) Uani d . 1 . .
H H16A 0.1822 0.5716 0.909 0.044 Uiso calc R 1 . .
H H16B 0.0185 0.4852 0.8677 0.044 Uiso calc R 1 . .
H H16C 0.0215 0.621 0.9395 0.044 Uiso calc R 1 . .
C C17 0.2609(5) 0.8150(4) 0.8572(3) 0.0207(8) Uani d . 1 . .
H H17A 0.2872 0.7761 0.9207 0.025 Uiso calc R 1 . .
H H17B 0.2889 0.9102 0.874 0.025 Uiso calc R 1 . .
O O5 0.6377(4) -0.0666(3) 0.5901(2) 0.0236(6) Uani d . 1 . .
N N2 0.7964(4) 0.2711(3) 0.4892(3) 0.0185(7) Uani d . 1 . .
C C12 0.6622(4) 0.3988(3) 0.6110(3) 0.0116(7) Uani d . 1 . .
C C10 0.6387(5) 0.6348(4) 0.6071(3) 0.0155(7) Uani d . 1 . .
H H10 0.5979 0.716 0.629 0.019 Uiso calc R 1 . .
C C11 0.6071(4) 0.5229(4) 0.6470(3) 0.0141(7) Uani d . 1 . .
H H11 0.5489 0.5285 0.6983 0.017 Uiso calc R 1 . .
C C5 0.6598(5) 0.1677(4) 0.5993(3) 0.0143(7) Uani d . 1 . .
C C6 0.7465(5) 0.1632(4) 0.5210(3) 0.0184(8) Uani d . 1 . .
H H6 0.7696 0.0799 0.4902 0.022 Uiso calc R 1 . .
C C7 0.7515(4) 0.3910(4) 0.5336(3) 0.0139(7) Uani d . 1 . .
C C4 0.6025(5) 0.0410(4) 0.6313(3) 0.0167(8) Uani d . 1 . .
C C8 0.7889(5) 0.5102(4) 0.4965(3) 0.0159(7) Uani d . 1 . .
H H8 0.8515 0.5073 0.4477 0.019 Uiso calc R 1 . .
C C9 0.7334(4) 0.6286(4) 0.5322(3) 0.0163(8) Uani d . 1 . .
H H9 0.7577 0.7064 0.5073 0.02 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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'
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 Re1 C2 . . 88.06(17) ?
C1 Re1 C3 . . 88.08(17) ?
C2 Re1 C3 . . 90.12(17) ?
C1 Re1 O4 . . 93.58(14) ?
C2 Re1 O4 . . 172.60(14) ?
C3 Re1 O4 . . 97.15(15) ?
C1 Re1 N1 . . 167.94(14) ?
C2 Re1 N1 . . 103.18(14) ?
C3 Re1 N1 . . 96.14(14) ?
O4 Re1 N1 . . 74.71(11) ?
C1 Re1 Cl1 . . 94.68(13) ?
C2 Re1 Cl1 . . 88.98(13) ?
C3 Re1 Cl1 . . 177.06(11) ?
O4 Re1 Cl1 . . 83.70(8) ?
N1 Re1 Cl1 . . 81.35(8) ?
O3 C3 Re1 . . 176.6(4) ?
C17 N3 C19 . . 111.5(3) ?
C17 N3 C13 . . 106.6(3) ?
C19 N3 C13 . . 110.3(3) ?
C17 N3 C15 . . 110.7(3) ?
C19 N3 C15 . . 106.6(3) ?
C13 N3 C15 . . 111.2(3) ?
C4 O4 Re1 . . 117.4(2) ?
C5 N1 C12 . . 117.2(3) ?
C5 N1 Re1 . . 112.5(2) ?
C12 N1 Re1 . . 129.9(2) ?
O2 C2 Re1 . . 178.7(4) ?
C14 C13 N3 . . 115.2(3) ?
C14 C13 H13A . . 108.5 ?
N3 C13 H13A . . 108.5 ?
C14 C13 H13B . . 108.5 ?
N3 C13 H13B . . 108.5 ?
H13A C13 H13B . . 107.5 ?
C16 C15 N3 . . 115.3(3) ?
C16 C15 H15A . . 108.4 ?
N3 C15 H15A . . 108.4 ?
C16 C15 H15B . . 108.4 ?
N3 C15 H15B . . 108.4 ?
H15A C15 H15B . . 107.5 ?
O1 C1 Re1 . . 177.9(4) ?
C19 C20 H20A . . 109.5 ?
C19 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C19 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
N3 C19 C20 . . 115.4(3) ?
N3 C19 H19A . . 108.4 ?
C20 C19 H19A . . 108.4 ?
N3 C19 H19B . . 108.4 ?
C20 C19 H19B . . 108.4 ?
H19A C19 H19B . . 107.5 ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
N3 C17 C18 . . 114.5(3) ?
N3 C17 H17A . . 108.6 ?
C18 C17 H17A . . 108.6 ?
N3 C17 H17B . . 108.6 ?
C18 C17 H17B . . 108.6 ?
H17A C17 H17B . . 107.6 ?
C6 N2 C7 . . 115.9(3) ?
N1 C12 C11 . . 120.9(3) ?
N1 C12 C7 . . 119.3(3) ?
C11 C12 C7 . . 119.7(3) ?
C11 C10 C9 . . 120.4(3) ?
C11 C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.1(4) ?
C10 C11 H11 . . 120 ?
C12 C11 H11 . . 120 ?
N1 C5 C6 . . 121.8(3) ?
N1 C5 C4 . . 117.0(3) ?
C6 C5 C4 . . 121.1(3) ?
N2 C6 C5 . . 123.3(3) ?
N2 C6 H6 . . 118.4 ?
C5 C6 H6 . . 118.4 ?
N2 C7 C12 . . 122.2(3) ?
N2 C7 C8 . . 118.7(3) ?
C12 C7 C8 . . 119.0(3) ?
O5 C4 O4 . . 127.0(4) ?
O5 C4 C5 . . 118.5(4) ?
O4 C4 C5 . . 114.5(3) ?
C9 C8 C7 . . 120.1(4) ?
C9 C8 H8 . . 120 ?
C7 C8 H8 . . 120 ?
C8 C9 C10 . . 120.6(3) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
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
Re1 C1 . 1.899(4) ?
Re1 C2 . 1.900(4) ?
Re1 C3 . 1.917(5) ?
Re1 O4 . 2.136(3) ?
Re1 N1 . 2.211(3) ?
Re1 Cl1 . 2.4825(16) ?
O3 C3 . 1.145(5) ?
N3 C17 . 1.511(5) ?
N3 C19 . 1.521(5) ?
N3 C13 . 1.521(5) ?
N3 C15 . 1.527(5) ?
O1 C1 . 1.164(5) ?
O4 C4 . 1.281(5) ?
N1 C5 . 1.319(5) ?
N1 C12 . 1.390(4) ?
O2 C2 . 1.160(5) ?
C13 C14 . 1.508(5) ?
C13 H13A . 0.97 ?
C13 H13B . 0.97 ?
C15 C16 . 1.510(6) ?
C15 H15A . 0.97 ?
C15 H15B . 0.97 ?
C20 C19 . 1.526(5) ?
C20 H20A . 0.96 ?
C20 H20B . 0.96 ?
C20 H20C . 0.96 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C18 C17 . 1.513(6) ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.97 ?
C19 H19B . 0.97 ?
C16 H16A . 0.96 ?
C16 H16B . 0.96 ?
C16 H16C . 0.96 ?
C17 H17A . 0.97 ?
C17 H17B . 0.97 ?
O5 C4 . 1.225(4) ?
N2 C6 . 1.315(5) ?
N2 C7 . 1.374(5) ?
C12 C11 . 1.405(5) ?
C12 C7 . 1.413(5) ?
C10 C11 . 1.360(5) ?
C10 C9 . 1.417(5) ?
C10 H10 . 0.93 ?
C11 H11 . 0.93 ?
C5 C6 . 1.410(5) ?
C5 C4 . 1.506(5) ?
C6 H6 . 0.93 ?
C7 C8 . 1.417(5) ?
C8 C9 . 1.356(5) ?
C8 H8 . 0.93 ?
C9 H9 . 0.93 ?
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
C10 H10 O5 1_565 0.93 2.35 3.046(5) 131
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 Re1 O4 C4 . . . . -159.2(3) ?
C3 Re1 O4 C4 . . . . 112.3(3) ?
Cl1 Re1 O4 C4 . . . . -64.9(3) ?
C2 Re1 N1 C5 . . . . 157.7(3) ?
C3 Re1 N1 C5 . . . . -110.7(3) ?
Cl1 Re1 N1 C5 . . . . 70.8(2) ?
C1 Re1 N1 C12 . . . . -174.0(6) ?
C3 Re1 N1 C12 . . . . 76.0(3) ?
O4 Re1 N1 C12 . . . . 171.8(3) ?
Cl1 Re1 N1 C12 . . . . -102.4(3) ?
C17 N3 C13 C14 . . . . -172.0(3) ?
C19 N3 C13 C14 . . . . 66.8(4) ?
C15 N3 C13 C14 . . . . -51.2(4) ?
C17 N3 C15 C16 . . . . 57.8(5) ?
C19 N3 C15 C16 . . . . 179.3(3) ?
C13 N3 C15 C16 . . . . -60.5(4) ?
C17 N3 C19 C20 . . . . -51.7(4) ?
C13 N3 C19 C20 . . . . 66.6(4) ?
C15 N3 C19 C20 . . . . -172.6(3) ?
C19 N3 C17 C18 . . . . -55.5(4) ?
C13 N3 C17 C18 . . . . -176.0(3) ?
C15 N3 C17 C18 . . . . 63.0(4) ?
C5 N1 C12 C11 . . . . 171.0(3) ?
Re1 N1 C12 C7 . . . . 167.3(2) ?
N1 C12 C11 C10 . . . . -176.3(3) ?
Re1 N1 C5 C6 . . . . -169.4(3) ?
C12 N1 C5 C4 . . . . -174.2(3) ?
Re1 N1 C5 C4 . . . . 11.5(4) ?
C4 C5 C6 N2 . . . . 178.8(4) ?
C6 N2 C7 C8 . . . . -174.6(3) ?
C11 C12 C7 N2 . . . . -174.3(3) ?
N1 C12 C7 C8 . . . . 179.0(3) ?
Re1 O4 C4 O5 . . . . 164.6(3) ?
N1 C5 C4 O5 . . . . -178.6(3) ?
C6 C5 C4 O4 . . . . -175.9(3) ?
N2 C7 C8 C9 . . . . 174.1(3) ?
