#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:22:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178384 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/06/4020651.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_4020651
loop_
_publ_author_name
'Jun Yin'
'Ronald L. Elsenbaumer'
_publ_section_title
;
 Efficient Synthesis and Characterization of
 Novel Bibenzimidazole Oligomers and Polymers as
 Potential Conjugated Chelating Ligands
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9436
_journal_page_last               9446
_journal_paper_doi               10.1021/jo051515h
_journal_volume                  70
_journal_year                    2005
_chemical_formula_sum            'C26 H15 F18 N4 O12'
_chemical_formula_weight         917.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 100.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.067(4)
_cell_length_b                   19.299(4)
_cell_length_c                   8.537(2)
_cell_measurement_temperature    293(2)
_cell_volume                     3579.0(12)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.703
_refine_ls_R_factor_obs          0.0755
_refine_ls_wR_factor_obs         0.1797
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4020651
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.1761(2) 0.4495(2) 0.5223(4) 0.0331(9) Uani 1 d . .
H1A H 0.1851(2) 0.4041(2) 0.5176(4) 0.040 Uiso 1 d R .
C2 C 0.1210(2) 0.4804(2) 0.4541(5) 0.0338(11) Uani 1 d . .
C3 C 0.0678(2) 0.4532(3) 0.3644(6) 0.0458(13) Uani 1 d . .
H3A H 0.0637(2) 0.4047(3) 0.3401(6) 0.055 Uiso 1 d R .
C4 C 0.0222(2) 0.4998(3) 0.3126(7) 0.0530(15) Uani 1 d . .
H4A H -0.0152(2) 0.4836(3) 0.2479(7) 0.064 Uiso 1 d R .
C5 C 0.0274(2) 0.5701(3) 0.3502(7) 0.054(2) Uani 1 d . .
H5A H -0.0064(2) 0.6006(3) 0.3123(7) 0.065 Uiso 1 d R .
C6 C 0.0794(2) 0.5972(3) 0.4396(7) 0.0463(13) Uani 1 d . .
H6A H 0.0831(2) 0.6455(3) 0.4656(7) 0.056 Uiso 1 d R .
C7 C 0.1269(2) 0.5505(2) 0.4926(6) 0.0344(11) Uani 1 d . .
N8 N 0.1851(2) 0.5593(2) 0.5797(5) 0.0355(10) Uani 1 d . .
H8A H 0.2012(2) 0.5996(2) 0.6201(5) 0.043 Uiso 1 d R .
C9 C 0.2137(2) 0.4982(2) 0.5947(5) 0.0316(11) Uani 1 d . .
C10 C 0.2758(2) 0.4866(2) 0.6779(5) 0.0301(10) Uani 1 d . .
N11 N 0.3044(2) 0.4254(2) 0.6939(4) 0.0320(9) Uani 1 d . .
H11A H 0.2880(2) 0.3848(2) 0.6559(4) 0.038 Uiso 1 d R .
C12 C 0.3632(2) 0.4347(2) 0.7770(5) 0.0312(11) Uani 1 d . .
C13 C 0.4106(2) 0.3893(2) 0.8250(7) 0.0476(14) Uani 1 d . .
H13A H 0.4066(2) 0.3409(2) 0.7986(7) 0.057 Uiso 1 d R .
C14 C 0.4637(2) 0.4163(2) 0.9111(7) 0.0439(13) Uani 1 d . .
H14A H 0.4974(2) 0.3854(2) 0.9463(7) 0.053 Uiso 1 d R .
C15 C 0.4711(2) 0.4874(2) 0.9516(5) 0.0295(10) Uani 1 d . .
C16 C 0.4227(2) 0.5322(2) 0.8990(5) 0.0323(11) Uani 1 d . .
H16A H 0.4258(2) 0.5809(2) 0.9220(5) 0.039 Uiso 1 d R .
C17 C 0.3694(2) 0.5043(2) 0.8127(5) 0.0303(10) Uani 1 d . .
N18 N 0.3138(2) 0.5354(2) 0.7489(5) 0.0353(10) Uani 1 d . .
H18A H 0.3048(2) 0.5807(2) 0.7544(5) 0.042 Uiso 1 d R .
O101 O 0.2317(2) 0.3226(2) 0.5499(4) 0.0475(9) Uani 1 d . .
O102 O 0.1948(2) 0.2260(2) 0.4255(5) 0.0533(10) Uani 1 d . .
C101 C 0.2344(2) 0.2611(2) 0.5119(6) 0.0392(12) Uani 1 d . .
C102 C 0.2949(3) 0.2240(3) 0.5804(7) 0.0491(14) Uani 1 d . .
F101 F 0.3041(2) 0.1687(2) 0.4996(5) 0.0834(12) Uani 1 d . .
F102 F 0.3427(2) 0.2650(2) 0.5831(6) 0.0897(13) Uani 1 d . .
F103 F 0.2949(2) 0.2039(2) 0.7274(5) 0.0947(14) Uani 1 d . .
O201 O 0.2587(2) 0.6618(2) 0.7264(5) 0.0489(10) Uani 1 d . .
O202 O 0.3104(2) 0.7597(2) 0.7186(7) 0.081(2) Uani 1 d . .
C201 C 0.2634(3) 0.7254(2) 0.7195(7) 0.0461(13) Uani 1 d . .
C202 C 0.2035(3) 0.7669(3) 0.7103(8) 0.058(2) Uani 1 d . .
F201 F 0.1543(2) 0.7278(2) 0.6832(6) 0.0974(15) Uani 1 d . .
F202 F 0.2029(2) 0.8010(2) 0.8458(5) 0.0856(12) Uani 1 d . .
F203 F 0.1982(2) 0.8140(2) 0.5977(6) 0.102(2) Uani 1 d . .
O301 O 0.1024(2) 0.2907(2) 0.2540(5) 0.0649(12) Uani 1 d . .
H301 H 0.1409(2) 0.2713(2) 0.3210(5) 0.078 Uiso 1 d R .
O302 O 0.0820(2) 0.1933(2) 0.1164(6) 0.0824(15) Uani 1 d . .
C301 C 0.0725(3) 0.2520(3) 0.1442(7) 0.0528(15) Uani 1 d . .
C302 C 0.0200(4) 0.2923(4) 0.0464(9) 0.074(2) Uani 1 d . .
F301 F -0.0158(2) 0.3201(4) 0.1311(6) 0.137(2) Uani 1 d . .
F302 F 0.0414(3) 0.3443(3) -0.0265(7) 0.154(3) Uani 1 d . .
F303 F -0.0121(2) 0.2560(3) -0.0644(6) 0.136(2) Uani 1 d . .
O401 O 0.1819(2) 0.4099(2) 0.9030(5) 0.0623(11) Uani 1 d . .
H401 H 0.1738(2) 0.3619(2) 0.8970(5) 0.075 Uiso 1 d R .
O402 O 0.1883(2) 0.4073(2) 1.1666(6) 0.0832(15) Uani 1 d . .
C401 C 0.1806(3) 0.4363(3) 1.0423(8) 0.0511(14) Uani 1 d . .
C402 C 0.1686(3) 0.5142(3) 1.0296(8) 0.058(2) Uani 1 d . .
F401 F 0.1758(3) 0.5421(2) 1.1698(5) 0.115(2) Uani 1 d . .
F402 F 0.2089(3) 0.5457(2) 0.9584(6) 0.110(2) Uani 1 d . .
F403 F 0.1163(3) 0.5286(3) 0.9588(11) 0.207(4) Uani 1 d . .
O501 O 0.3409(2) 0.6082(2) 0.1869(6) 0.083(2) Uani 1 d . .
H501 H 0.3294(2) 0.6602(2) 0.2035(6) 0.099 Uiso 1 d R .
O502 O 0.3050(3) 0.5818(3) 0.4083(6) 0.094(2) Uani 1 d . .
C501 C 0.3313(3) 0.5681(3) 0.3025(8) 0.060(2) Uani 1 d . .
C502 C 0.3570(5) 0.4970(4) 0.2868(10) 0.084(2) Uani 1 d . .
F501 F 0.3346(3) 0.4692(2) 0.1438(6) 0.120(2) Uani 1 d . .
F502 F 0.3443(4) 0.4552(2) 0.3920(7) 0.175(3) Uani 1 d . .
F503 F 0.4169(3) 0.4987(3) 0.2843(7) 0.129(2) Uani 1 d . .
O601 O 0.4050(2) 0.6853(2) 0.6724(7) 0.086(2) Uani 1 d . .
H601 H 0.3760(2) 0.7107(2) 0.7441(7) 0.103 Uiso 1 d R .
O602 O 0.4369(3) 0.7783(3) 0.5646(9) 0.128(3) Uani 1 d . .
C601 C 0.4420(3) 0.7202(4) 0.6057(9) 0.071(2) Uani 1 d . .
C602 C 0.4956(4) 0.6774(5) 0.5762(15) 0.101(3) Uani 1 d . .
F601 F 0.4839(3) 0.6238(5) 0.5063(15) 0.258(6) Uani 1 d . .
F602 F 0.5336(4) 0.7093(4) 0.5113(14) 0.234(5) Uani 1 d . .
F603 F 0.5286(4) 0.6571(6) 0.7067(11) 0.234(5) Uani 1 d . .
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
N1 C9 1.333(6) . ?
N1 C2 1.387(6) . ?
C2 C3 1.386(7) . ?
C2 C7 1.394(6) . ?
C3 C4 1.366(7) . ?
C4 C5 1.394(8) . ?
C5 C6 1.365(8) . ?
C6 C7 1.395(7) . ?
C7 N8 1.376(6) . ?
N8 C9 1.333(6) . ?
C9 C10 1.444(6) . ?
C10 N18 1.334(6) . ?
C10 N11 1.336(5) . ?
N11 C12 1.377(6) . ?
C12 C13 1.371(6) . ?
C12 C17 1.379(6) . ?
C13 C14 1.371(7) . ?
C14 C15 1.418(6) . ?
C15 C16 1.386(6) . ?
C15 C15 1.476(9) 3_667 ?
C16 C17 1.381(6) . ?
C17 N18 1.389(6) . ?
O101 C101 1.234(5) . ?
O102 C101 1.241(6) . ?
C101 C102 1.537(7) . ?
C102 F101 1.307(6) . ?
C102 F103 1.313(7) . ?
C102 F102 1.316(6) . ?
O201 C201 1.233(6) . ?
O202 C201 1.232(6) . ?
C201 C202 1.537(8) . ?
C202 F203 1.314(7) . ?
C202 F201 1.309(7) . ?
C202 F202 1.333(7) . ?
O301 C301 1.288(6) . ?
O302 C301 1.184(7) . ?
C301 C302 1.518(9) . ?
C302 F301 1.279(8) . ?
C302 F303 1.286(8) . ?
C302 F302 1.311(8) . ?
O401 C401 1.299(7) . ?
O402 C401 1.185(7) . ?
C401 C402 1.526(8) . ?
C402 F403 1.237(8) . ?
C402 F401 1.296(7) . ?
C402 F402 1.311(7) . ?
O501 C501 1.300(7) . ?
O502 C501 1.186(7) . ?
C501 C502 1.500(9) . ?
C502 F502 1.274(7) . ?
C502 F503 1.325(10) . ?
C502 F501 1.345(9) . ?
O601 C601 1.269(7) . ?
O602 C601 1.174(8) . ?
C601 C602 1.499(11) . ?
C602 F601 1.200(11) . ?
C602 F602 1.245(10) . ?
C602 F603 1.280(12) . ?
