#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/10/07/1100747.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1100747
loop_
_publ_author_name
'Natasha J. Lundin'
'Penny J. Walsh'
'Sarah L. Howell'
'John J. McGarvey'
'Allan G. Blackman'
'Keith C. Gordon'
_publ_contact_author_address
;Department of Chemistry

University of Otago

P.O. Box 56

Dunedin

New Zealand

;
_publ_contact_author_email       kgordon@alkali.otago.ac.nz
_publ_contact_author_fax         '+64 3 479 7906'
_publ_contact_author_name        'Keith Gordon'
_publ_contact_author_phone       '+64 3 479 7599'
_publ_section_title
;

Complexes of Functionalized Dipyrido[3,2-a:2',3'-c]-phenazine: A

Synthetic, Spectroscopic, Structural, and Density Functional Theory Study

;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3551
_journal_page_last               3560
_journal_paper_doi               10.1021/ic050179k
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C22 H12 Br Cl N4 O4 Re'
_chemical_formula_weight         697.92
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2004-08-30T13:27:07-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.000
_cell_angle_beta                 114.936(5)
_cell_angle_gamma                90.000
_cell_formula_units_Z            8
_cell_length_a                   19.506(5)
_cell_length_b                   18.043(5)
_cell_length_c                   13.320(5)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    164(2)
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.3
_cell_volume                     4251(2)
_computing_cell_refinement       'Bruker SMART (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'WinGX (Farrugia, 1999)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al, 1997)'
_diffrn_ambient_temperature      164(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            26269
_diffrn_reflns_theta_full        26.54
_diffrn_reflns_theta_max         26.54
_diffrn_reflns_theta_min         1.95
_exptl_absorpt_coefficient_mu    7.762
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.709676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.181
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       block
_exptl_crystal_F_000             2648
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         2.203
_refine_diff_density_min         -1.684
_refine_diff_density_rms         0.134
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         4381
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0411P)²+40.1104P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                3956
_reflns_number_total             4381
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic050179ksi20050202_061153.cif
_cod_data_source_block           njldm
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_database_code               1100747
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Re1 Re 0.656870(10) 0.154175(10) 0.580330(16) 0.02564(8) Uani 1 1 d . . .
Br1 Br 1.26297(6) -0.10104(8) 1.06764(9) 0.0443(4) Uani 0.501(2) 1 d P A 1
Br1A Br 1.17956(9) -0.23632(9) 1.02240(13) 0.0662(6) Uani 0.499(2) 1 d P A 2
Cl1 Cl 0.69696(9) 0.10626(7) 0.44017(11) 0.0382(3) Uani 1 1 d . . .
N2 N 0.7769(2) 0.1700(2) 0.6792(3) 0.0238(8) Uani 1 1 d . . .
C300 C 0.5538(3) 0.1330(3) 0.4888(6) 0.0441(15) Uani 1 1 d . . .
C3 C 0.7672(3) -0.0910(3) 0.7238(4) 0.0312(11) Uani 1 1 d . . .
H3 H 0.7898 -0.137 0.7467 0.037 Uiso 1 1 calc R . .
C6 C 0.8167(3) 0.1079(3) 0.7227(4) 0.0235(9) Uani 1 1 d . . .
C100 C 0.6356(3) 0.2527(3) 0.5228(4) 0.0301(11) Uani 1 1 d . . .
N1 N 0.6984(2) 0.0460(2) 0.6512(3) 0.0249(8) Uani 1 1 d . . .
N3 N 1.0084(2) 0.0420(3) 0.8774(3) 0.0285(9) Uani 1 1 d . A .
N4 N 0.9273(2) -0.0933(3) 0.8293(4) 0.0315(9) Uani 1 1 d . . .
C4 C 0.8111(3) -0.0272(3) 0.7429(4) 0.0250(10) Uani 1 1 d . . .
C7 C 0.8950(3) 0.1086(3) 0.7828(4) 0.0256(10) Uani 1 1 d . . .
C10 C 0.8131(3) 0.2340(3) 0.6954(4) 0.0311(11) Uani 1 1 d . . .
H10 H 0.7857 0.2769 0.6654 0.037 Uiso 1 1 calc R . .
C11 C 0.9342(3) 0.0393(3) 0.8228(4) 0.0266(10) Uani 1 1 d . . .
C9 C 0.8914(3) 0.2389(3) 0.7565(5) 0.0351(12) Uani 1 1 d . . .
H9 H 0.9156 0.2846 0.7665 0.042 Uiso 1 1 calc R . .
C13 C 1.0039(3) -0.0911(3) 0.8829(4) 0.0339(12) Uani 1 1 d . A .
C200 C 0.6287(4) 0.1859(3) 0.6939(6) 0.0436(14) Uani 1 1 d . . .
C2 C 0.6904(3) -0.0847(3) 0.6708(5) 0.0373(13) Uani 1 1 d . . .
H2 H 0.66 -0.1265 0.6582 0.045 Uiso 1 1 calc R . .
O3 O 0.4914(2) 0.1209(3) 0.4307(5) 0.0685(16) Uani 1 1 d . . .
C16 C 1.1601(3) -0.0903(4) 0.9951(5) 0.0476(17) Uani 1 1 d . . .
O1 O 0.6229(2) 0.3118(2) 0.4898(4) 0.0399(9) Uani 1 1 d . . .
C8 C 0.9319(3) 0.1770(3) 0.8008(4) 0.0314(11) Uani 1 1 d . . .
H8 H 0.9838 0.1799 0.8429 0.038 Uiso 1 1 calc R . .
C1 C 0.6579(3) -0.0155(3) 0.6359(4) 0.0314(11) Uani 1 1 d . . .
H1 H 0.6055 -0.0122 0.6002 0.038 Uiso 1 1 calc R . .
C15 C 1.1203(4) -0.1577(4) 0.9683(6) 0.0523(18) Uani 1 1 d . A .
C17 C 1.1237(3) -0.0243(4) 0.9661(4) 0.0384(13) Uani 1 1 d . A .
H17 H 1.1508 0.0199 0.9839 0.046 Uiso 1 1 calc R . .
O2 O 0.6084(4) 0.2074(3) 0.7563(5) 0.0702(16) Uani 1 1 d . . .
C12 C 0.8931(3) -0.0287(3) 0.8000(4) 0.0241(9) Uani 1 1 d . . .
C18 C 1.0440(3) -0.0237(3) 0.9084(4) 0.0319(11) Uani 1 1 d . . .
C5 C 0.7743(3) 0.0399(3) 0.7051(4) 0.0227(9) Uani 1 1 d . . .
C14 C 1.0440(4) -0.1583(4) 0.9132(5) 0.0450(15) Uani 1 1 d . . .
H14 H 1.0182 -0.2032 0.8954 0.054 Uiso 1 1 calc R A .
O4 O 0.53070(19) -0.0542(2) 0.3695(2) 0.0268(7) Uani 1 1 d . . .
H4 H 0.5488 -0.0955 0.3901 0.04 Uiso 1 1 calc R . .
C19 C 0.5659(7) -0.0218(6) 0.3155(9) 0.109(5) Uani 1 1 d . . .
H19A H 0.6011 0.0141 0.3628 0.164 Uiso 1 1 calc R . .
H19B H 0.5295 0.0025 0.2509 0.164 Uiso 1 1 calc R . .
H19C H 0.5926 -0.0585 0.2937 0.164 Uiso 1 1 calc R . .
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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C300 Re1 C200 89.4(3) . . ?
C300 Re1 C100 86.4(2) . . ?
C200 Re1 C100 87.3(2) . . ?
C300 Re1 N2 175.1(2) . . ?
C200 Re1 N2 94.4(2) . . ?
C100 Re1 N2 96.76(18) . . ?
C300 Re1 N1 101.4(2) . . ?
C200 Re1 N1 96.0(2) . . ?
C100 Re1 N1 171.51(17) . . ?
N2 Re1 N1 75.21(15) . . ?
C300 Re1 Cl1 91.8(2) . . ?
C200 Re1 Cl1 176.46(19) . . ?
C100 Re1 Cl1 96.14(16) . . ?
N2 Re1 Cl1 84.26(11) . . ?
N1 Re1 Cl1 80.51(11) . . ?
C10 N2 C6 119.0(4) . . ?
C10 N2 Re1 125.4(3) . . ?
C6 N2 Re1 115.5(3) . . ?
O3 C300 Re1 178.1(6) . . ?
C2 C3 C4 118.8(5) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
N2 C6 C7 122.2(4) . . ?
N2 C6 C5 116.8(4) . . ?
C7 C6 C5 121.0(5) . . ?
O1 C100 Re1 179.0(5) . . ?
C1 N1 C5 117.5(4) . . ?
C1 N1 Re1 126.6(3) . . ?
C5 N1 Re1 115.4(3) . . ?
C11 N3 C18 116.1(5) . . ?
C12 N4 C13 115.9(5) . . ?
C5 C4 C3 118.1(4) . . ?
C5 C4 C12 119.5(4) . . ?
C3 C4 C12 122.5(5) . . ?
C6 C7 C8 117.9(5) . . ?
C6 C7 C11 119.0(4) . . ?
C8 C7 C11 123.2(4) . . ?
N2 C10 C9 121.8(5) . . ?
N2 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N3 C11 C12 122.5(5) . . ?
N3 C11 C7 117.3(5) . . ?
C12 C11 C7 120.2(4) . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N4 C13 C18 121.9(5) . . ?
N4 C13 C14 118.8(6) . . ?
C18 C13 C14 119.3(5) . . ?
O2 C200 Re1 175.6(6) . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C17 C16 C15 121.4(6) . . ?
C17 C16 Br1 124.5(6) . . ?
C15 C16 Br1 114.0(5) . . ?
C9 C8 C7 119.4(5) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
N1 C1 C2 122.8(4) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C14 C15 C16 120.6(6) . . ?
C14 C15 Br1A 126.2(6) . . ?
C16 C15 Br1A 113.1(5) . . ?
C16 C17 C18 118.9(6) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
N4 C12 C11 121.9(4) . . ?
N4 C12 C4 118.6(4) . . ?
C11 C12 C4 119.4(4) . . ?
N3 C18 C13 121.6(4) . . ?
N3 C18 C17 118.6(5) . . ?
C13 C18 C17 119.8(5) . . ?
N1 C5 C4 123.1(4) . . ?
N1 C5 C6 116.2(4) . . ?
C4 C5 C6 120.6(4) . . ?
C15 C14 C13 120.0(7) . . ?
C15 C14 H14 120 . . ?
C13 C14 H14 120 . . ?
C19 O4 H4 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Re1 C300 1.900(6) . ?
Re1 C200 1.902(6) . ?
Re1 C100 1.911(5) . ?
Re1 N2 2.168(4) . ?
Re1 N1 2.171(4) . ?
Re1 Cl1 2.4648(15) . ?
Br1 C16 1.834(6) . ?
Br1A C15 1.779(6) . ?
N2 C10 1.323(6) . ?
N2 C6 1.346(6) . ?
C300 O3 1.154(7) . ?
C3 C2 1.365(7) . ?
C3 C4 1.393(7) . ?
C3 H3 0.93 . ?
C6 C7 1.394(6) . ?
C6 C5 1.442(6) . ?
C100 O1 1.141(7) . ?
N1 C1 1.327(6) . ?
N1 C5 1.352(6) . ?
N3 C11 1.319(6) . ?
N3 C18 1.347(7) . ?
N4 C12 1.318(7) . ?
N4 C13 1.357(7) . ?
C4 C5 1.389(7) . ?
C4 C12 1.454(6) . ?
C7 C8 1.397(7) . ?
C7 C11 1.446(7) . ?
C10 C9 1.399(7) . ?
C10 H10 0.93 . ?
C11 C12 1.425(7) . ?
C9 C8 1.351(8) . ?
C9 H9 0.93 . ?
C13 C18 1.406(8) . ?
C13 C14 1.408(8) . ?
C200 O2 1.131(8) . ?
C2 C1 1.388(8) . ?
C2 H2 0.93 . ?
C16 C17 1.356(9) . ?
C16 C15 1.404(11) . ?
C8 H8 0.93 . ?
C1 H1 0.93 . ?
C15 C14 1.353(9) . ?
C17 C18 1.416(7) . ?
C17 H17 0.93 . ?
C14 H14 0.93 . ?
O4 C19 1.321(9) . ?
O4 H4 0.82 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
