#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/08/2220861.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_2220861
loop_
_publ_author_name
'Kia, Reza'
'Fun, Hoong-Kun'
_publ_section_title
fac-[N,N'-Bis(3-chloro-2-fluorobenzylidene)ethylenediamine]bromidotricarbonylrhenium(I)
_journal_coeditor_code           LH2753
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m192
_journal_page_last               m193
_journal_paper_doi               10.1107/S1600536809001044
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Re Br (C16 H12 Cl2 F2 N2) (C O)3]'
_chemical_formula_moiety         'C19 H12 Br Cl2 F2 N2 O3 Re'
_chemical_formula_sum            'C19 H12 Br Cl2 F2 N2 O3 Re'
_chemical_formula_weight         691.32
_chemical_name_systematic
fac-[N,N'-Bis(3-chloro-2-fluorobenzylidene)ethylenediamine]bromidotricarbonylrhenium(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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                116.504(2)
_cell_angle_beta                 99.707(2)
_cell_angle_gamma                90.404(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3238(3)
_cell_length_b                   12.3077(4)
_cell_length_c                   13.1984(5)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      36.53
_cell_measurement_theta_min      3.08
_cell_volume                     1044.84(7)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.00(10)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type
;
Bruker SMART APEXII CCD area-detector
;
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            33300
_diffrn_reflns_theta_full        35.00
_diffrn_reflns_theta_max         35.00
_diffrn_reflns_theta_min         2.83
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    8.025
_exptl_absorpt_correction_T_max  0.5686
_exptl_absorpt_correction_T_min  0.1704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         4.357
_refine_diff_density_min         -2.863
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         9014
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0503
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.043P)²+25.3509P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1537
_reflns_number_gt                7668
_reflns_number_total             9014
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2753.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_database_code               2220861
_cod_database_fobs_code          2220861
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 0.41651(4) 0.44687(2) 0.17913(2) 0.01814(7) Uani d . 1 . .
Br Br1 0.59914(10) 0.30823(6) 0.26094(6) 0.02132(13) Uani d . 1 . .
Cl Cl1 -0.2702(4) -0.0324(3) -0.2767(2) 0.0453(6) Uani d . 1 . .
Cl Cl2 1.1905(3) 0.8265(2) 0.5091(2) 0.0379(5) Uani d . 1 . .
F F1 -0.2477(7) 0.1706(5) -0.0492(5) 0.0332(10) Uani d . 1 . .
F F2 0.8904(7) 0.6865(5) 0.5305(5) 0.0304(10) Uani d . 1 . .
O O1 0.1897(9) 0.6185(6) 0.1033(7) 0.0365(14) Uani d . 1 . .
O O2 0.4182(9) 0.2812(6) -0.0766(5) 0.0291(11) Uani d . 1 . .
O O3 0.7869(8) 0.5564(6) 0.1675(5) 0.0293(11) Uani d . 1 . .
N N1 0.1581(9) 0.3695(6) 0.1978(5) 0.0216(10) Uani d . 1 . .
N N2 0.4113(9) 0.5578(6) 0.3623(5) 0.0215(10) Uani d . 1 . .
C C1 0.2797(10) 0.5521(7) 0.1317(6) 0.0236(12) Uani d . 1 . .
C C2 0.4139(10) 0.3398(7) 0.0196(6) 0.0240(12) Uani d . 1 . .
C C3 0.6462(10) 0.5171(7) 0.1739(6) 0.0231(12) Uani d . 1 . .
C C4 -0.0837(11) 0.1231(7) -0.0633(7) 0.0260(13) Uani d . 1 . .
C C5 -0.0743(12) 0.0240(7) -0.1673(7) 0.0275(14) Uani d . 1 . .
C C6 0.0927(13) -0.0300(7) -0.1816(7) 0.0293(15) Uani d . 1 . .
H H6A 0.1011 -0.0974 -0.2506 0.035 Uiso calc R 1 . .
C C7 0.2454(12) 0.0175(8) -0.0925(7) 0.0304(15) Uani d . 1 . .
H H7A 0.3565 -0.0185 -0.1019 0.036 Uiso calc R 1 . .
C C8 0.2359(10) 0.1165(6) 0.0091(6) 0.0209(11) Uani d . 1 . .
H H8A 0.3399 0.1465 0.0683 0.025 Uiso calc R 1 . .
C C9 0.0687(10) 0.1738(7) 0.0249(6) 0.0230(12) Uani d . 1 . .
C C10 0.0427(10) 0.2764(7) 0.1340(6) 0.0237(12) Uani d . 1 . .
H H10A -0.0681 0.2728 0.1584 0.028 Uiso calc R 1 . .
C C11 0.1005(10) 0.4586(6) 0.3060(6) 0.0219(12) Uani d . 1 . .
H H11A 0.0068 0.4196 0.3259 0.026 Uiso calc R 1 . .
H H11B 0.0491 0.5263 0.2959 0.026 Uiso calc R 1 . .
C C12 0.2731(10) 0.5034(7) 0.4001(6) 0.0222(12) Uani d . 1 . .
H H12A 0.2437 0.5638 0.4720 0.027 Uiso calc R 1 . .
H H12B 0.3218 0.4361 0.4121 0.027 Uiso calc R 1 . .
C C13 0.5117(10) 0.6545(7) 0.4396(6) 0.0231(12) Uani d . 1 . .
H H13A 0.5006 0.6803 0.5159 0.028 Uiso calc R 1 . .
C C14 0.6436(10) 0.7276(6) 0.4158(6) 0.0215(11) Uani d . 1 . .
C C15 0.8330(10) 0.7421(7) 0.4645(6) 0.0237(12) Uani d . 1 . .
C C16 0.9615(11) 0.8108(7) 0.4457(7) 0.0270(14) Uani d . 1 . .
C C17 0.8965(15) 0.8671(9) 0.3764(7) 0.0369(13) Uani d . 1 . .
H H17A 0.9809 0.9116 0.3607 0.044 Uiso calc R 1 . .
C C18 0.7106(15) 0.8577(8) 0.3315(7) 0.0354(19) Uani d . 1 . .
H H18A 0.6697 0.9000 0.2898 0.042 Uiso calc R 1 . .
C C19 0.5845(16) 0.7865(9) 0.3474(7) 0.0369(13) Uani d . 1 . .
H H19A 0.4598 0.7770 0.3130 0.044 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 0.0000 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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Re Re -1.0185 7.2310 '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 C3 . . 91.3(3) ?
C1 Re1 C2 . . 88.3(3) ?
C3 Re1 C2 . . 84.4(3) ?
C1 Re1 N2 . . 94.3(3) ?
C3 Re1 N2 . . 98.8(3) ?
C2 Re1 N2 . . 175.8(3) ?
C1 Re1 N1 . . 90.7(3) ?
C3 Re1 N1 . . 176.1(3) ?
C2 Re1 N1 . . 99.0(3) ?
N2 Re1 N1 . . 77.7(2) y
C1 Re1 Br1 . . 175.6(2) ?
C3 Re1 Br1 . . 90.5(2) ?
C2 Re1 Br1 . . 95.9(2) ?
N2 Re1 Br1 . . 81.48(16) ?
N1 Re1 Br1 . . 87.24(16) ?
C10 N1 C11 . . 115.3(6) ?
C10 N1 Re1 . . 135.2(5) ?
C11 N1 Re1 . . 109.0(4) ?
C13 N2 C12 . . 117.3(6) ?
C13 N2 Re1 . . 131.3(5) ?
C12 N2 Re1 . . 111.3(4) ?
O1 C1 Re1 . . 178.3(7) ?
O2 C2 Re1 . . 175.8(7) ?
O3 C3 Re1 . . 177.7(7) ?
F1 C4 C9 . . 119.6(7) ?
F1 C4 C5 . . 118.3(7) ?
C9 C4 C5 . . 122.1(8) ?
C4 C5 C6 . . 119.1(8) ?
C4 C5 Cl1 . . 119.7(7) ?
C6 C5 Cl1 . . 121.2(6) ?
C7 C6 C5 . . 119.4(7) ?
C7 C6 H6A . . 120.3 ?
C5 C6 H6A . . 120.3 ?
C8 C7 C6 . . 121.2(8) ?
C8 C7 H7A . . 119.4 ?
C6 C7 H7A . . 119.4 ?
C7 C8 C9 . . 120.4(7) ?
C7 C8 H8A . . 119.8 ?
C9 C8 H8A . . 119.8 ?
C4 C9 C8 . . 117.8(7) ?
C4 C9 C10 . . 117.9(7) ?
C8 C9 C10 . . 124.0(7) ?
N1 C10 C9 . . 126.0(7) ?
N1 C10 H10A . . 117.0 ?
C9 C10 H10A . . 117.0 ?
N1 C11 C12 . . 107.0(6) ?
N1 C11 H11A . . 110.3 ?
C12 C11 H11A . . 110.3 ?
N1 C11 H11B . . 110.3 ?
C12 C11 H11B . . 110.3 ?
H11A C11 H11B . . 108.6 ?
N2 C12 C11 . . 107.3(6) ?
N2 C12 H12A . . 110.3 ?
C11 C12 H12A . . 110.3 ?
N2 C12 H12B . . 110.3 ?
C11 C12 H12B . . 110.3 ?
H12A C12 H12B . . 108.5 ?
N2 C13 C14 . . 124.7(7) ?
N2 C13 H13A . . 117.7 ?
C14 C13 H13A . . 117.7 ?
C15 C14 C19 . . 118.4(7) ?
C15 C14 C13 . . 119.6(6) ?
C19 C14 C13 . . 122.0(7) ?
F2 C15 C16 . . 119.6(7) ?
F2 C15 C14 . . 118.7(6) ?
C16 C15 C14 . . 121.7(7) ?
C15 C16 C17 . . 118.0(8) ?
C15 C16 Cl2 . . 119.4(7) ?
C17 C16 Cl2 . . 122.6(7) ?
C18 C17 C16 . . 121.2(9) ?
C18 C17 H17A . . 119.4 ?
C16 C17 H17A . . 119.4 ?
C17 C18 C19 . . 120.6(9) ?
C17 C18 H18A . . 119.7 ?
C19 C18 H18A . . 119.7 ?
C18 C19 C14 . . 120.1(10) ?
C18 C19 H19A . . 120.0 ?
C14 C19 H19A . . 120.0 ?
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 . 1.898(7) y
Re1 C3 . 1.911(8) y
Re1 C2 . 1.918(7) y
Re1 N2 . 2.190(6) y
Re1 N1 . 2.211(6) y
Re1 Br1 . 2.6564(7) y
Cl1 C5 . 1.737(9) ?
Cl2 C16 . 1.711(9) ?
F1 C4 . 1.344(9) ?
F2 C15 . 1.347(9) ?
O1 C1 . 1.201(9) ?
O2 C2 . 1.153(9) ?
O3 C3 . 1.167(9) ?
N1 C10 . 1.273(10) ?
N1 C11 . 1.494(9) ?
N2 C13 . 1.284(10) ?
N2 C12 . 1.476(9) ?
C4 C9 . 1.376(11) ?
C4 C5 . 1.384(11) ?
C5 C6 . 1.397(12) ?
C6 C7 . 1.382(13) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.364(11) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.417(10) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.476(10) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.514(10) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.478(10) ?
C13 H13A . 0.9300 ?
C14 C15 . 1.401(10) ?
C14 C19 . 1.408(12) ?
C15 C16 . 1.385(11) ?
C16 C17 . 1.402(13) ?
C17 C18 . 1.372(15) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.373(13) ?
C18 H18A . 0.9300 ?
C19 H19A . 0.9300 ?
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
C8 H8A Br1 . 0.9300 2.8000 3.691(7) 161.00 y
C10 H10A Br1 1_455 0.9300 2.9300 3.845(7) 170.00 y
C11 H11B O3 1_455 0.9700 2.4800 3.264(10) 137.00 y
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 N1 C10 . . . . 95.2(8) ?
C2 Re1 N1 C10 . . . . 6.9(8) ?
N2 Re1 N1 C10 . . . . -170.6(8) ?
Br1 Re1 N1 C10 . . . . -88.7(7) ?
C1 Re1 N1 C11 . . . . -76.0(5) ?
C2 Re1 N1 C11 . . . . -164.3(5) ?
N2 Re1 N1 C11 . . . . 18.2(4) ?
Br1 Re1 N1 C11 . . . . 100.1(4) ?
C1 Re1 N2 C13 . . . . -81.1(7) ?
C3 Re1 N2 C13 . . . . 10.9(7) ?
N1 Re1 N2 C13 . . . . -170.9(7) ?
Br1 Re1 N2 C13 . . . . 100.1(7) ?
C1 Re1 N2 C12 . . . . 102.9(5) ?
C3 Re1 N2 C12 . . . . -165.1(5) ?
N1 Re1 N2 C12 . . . . 13.2(4) ?
Br1 Re1 N2 C12 . . . . -75.9(4) ?
F1 C4 C5 C6 . . . . -177.1(7) ?
C9 C4 C5 C6 . . . . 3.0(12) ?
F1 C4 C5 Cl1 . . . . 2.0(10) ?
C9 C4 C5 Cl1 . . . . -177.9(6) ?
C4 C5 C6 C7 . . . . -0.9(12) ?
Cl1 C5 C6 C7 . . . . -180.0(7) ?
C5 C6 C7 C8 . . . . -0.2(13) ?
C6 C7 C8 C9 . . . . -0.8(12) ?
F1 C4 C9 C8 . . . . 176.3(7) ?
C5 C4 C9 C8 . . . . -3.9(11) ?
F1 C4 C9 C10 . . . . 2.4(11) ?
C5 C4 C9 C10 . . . . -177.8(7) ?
C7 C8 C9 C4 . . . . 2.7(11) ?
C7 C8 C9 C10 . . . . 176.2(7) ?
C11 N1 C10 C9 . . . . -178.1(7) ?
Re1 N1 C10 C9 . . . . 11.1(12) ?
C4 C9 C10 N1 . . . . -142.2(8) ?
C8 C9 C10 N1 . . . . 44.3(12) ?
C10 N1 C11 C12 . . . . 140.9(7) ?
Re1 N1 C11 C12 . . . . -46.0(6) ?
C13 N2 C12 C11 . . . . 141.5(7) ?
Re1 N2 C12 C11 . . . . -41.9(6) ?
N1 C11 C12 N2 . . . . 58.1(7) ?
C12 N2 C13 C14 . . . . -173.8(6) ?
Re1 N2 C13 C14 . . . . 10.4(11) ?
N2 C13 C14 C15 . . . . -119.2(8) ?
N2 C13 C14 C19 . . . . 62.3(11) ?
C19 C14 C15 F2 . . . . 179.7(7) ?
C13 C14 C15 F2 . . . . 1.2(10) ?
C19 C14 C15 C16 . . . . -0.9(11) ?
C13 C14 C15 C16 . . . . -179.4(7) ?
F2 C15 C16 C17 . . . . 179.9(7) ?
C14 C15 C16 C17 . . . . 0.5(11) ?
F2 C15 C16 Cl2 . . . . -1.4(10) ?
C14 C15 C16 Cl2 . . . . 179.2(6) ?
C15 C16 C17 C18 . . . . 2.0(12) ?
Cl2 C16 C17 C18 . . . . -176.7(7) ?
C16 C17 C18 C19 . . . . -4.0(14) ?
C17 C18 C19 C14 . . . . 3.6(13) ?
C15 C14 C19 C18 . . . . -1.2(12) ?
C13 C14 C19 C18 . . . . 177.3(8) ?
