#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/02/7150282.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_7150282
loop_
_publ_author_name
'Wong, Wallace W. H.'
'Vickers, Matthew S.'
'Cowley, Andrew R.'
'Paul, Rowena L.'
'Beer, Paul D.'
_publ_section_title
;
 Tetrakis(imidazolium) macrocyclic receptors for anion binding.
;
_journal_issue                   23
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4201
_journal_page_last               4208
_journal_paper_doi               10.1039/b510068b
_journal_volume                  3
_journal_year                    2005
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C17 H16 N4 '
_chemical_formula_sum            'C17 H16 N4'
_chemical_formula_weight         276.34
_chemical_name_systematic
;
?
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.1991(4)
_cell_length_b                   8.6736(2)
_cell_length_c                   12.6158(2)
_cell_measurement_reflns_used    3483
_cell_measurement_temperature    150
_cell_measurement_theta_max      27
_cell_measurement_theta_min      5
_cell_volume                     2757.40(9)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18754
_diffrn_reflns_theta_full        27.487
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         5.143
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' colourless '
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1219
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0337
_refine_ls_shift/su_max          0.000347
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
0.528 0.262 0.252
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0596
_refine_ls_wR_factor_gt          0.0381
_refine_ls_wR_factor_ref         0.0381
_reflns_limit_h_max              32
_reflns_limit_h_min              0
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2021
_reflns_number_total             3142
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b510068b.txt
_cod_data_source_block           Compound_X
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_original_sg_symbol_H-M      'P b c n '
_cod_original_formula_sum        ' C17 H16 N4 '
_cod_database_code               7150282
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
-x+1/2,-y+1/2,z+1/2
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_occupancy
_atom_site_adp_type
N1 N 0.39260(4) 0.45428(12) 0.50743(9) 0.0242 1.0000 Uani
C1 C 0.38108(5) 0.46956(17) 0.61232(11) 0.0295 1.0000 Uani
N2 N 0.40646(5) 0.58189(15) 0.66008(9) 0.0315 1.0000 Uani
C2 C 0.43814(5) 0.64496(16) 0.58071(11) 0.0257 1.0000 Uani
C3 C 0.43013(5) 0.56620(15) 0.48478(10) 0.0227 1.0000 Uani
C4 C 0.45850(5) 0.59933(16) 0.39287(11) 0.0261 1.0000 Uani
C5 C 0.49582(6) 0.71602(16) 0.40039(12) 0.0300 1.0000 Uani
C6 C 0.50405(6) 0.79692(16) 0.49515(13) 0.0315 1.0000 Uani
C7 C 0.47556(6) 0.76314(16) 0.58591(12) 0.0304 1.0000 Uani
C8 C 0.37029(5) 0.34111(16) 0.43448(11) 0.0262 1.0000 Uani
N3 N 0.25854(4) 0.32058(14) 0.23427(9) 0.0282 1.0000 Uani
C9 C 0.32181(5) 0.40021(15) 0.37512(11) 0.0250 1.0000 Uani
N4 N 0.22057(5) 0.39813(16) 0.08179(10) 0.0380 1.0000 Uani
C10 C 0.30005(6) 0.26992(16) 0.30687(11) 0.0295 1.0000 Uani
C11 C 0.26351(6) 0.3449(2) 0.12792(12) 0.0361 1.0000 Uani
C12 C 0.18398(6) 0.40989(16) 0.16403(11) 0.0284 1.0000 Uani
C13 C 0.20699(5) 0.36106(15) 0.25967(11) 0.0247 1.0000 Uani
C14 C 0.17934(6) 0.35737(16) 0.35494(11) 0.0288 1.0000 Uani
C15 C 0.12681(6) 0.40336(18) 0.35157(12) 0.0325 1.0000 Uani
C16 C 0.10326(6) 0.45302(16) 0.25693(13) 0.0336 1.0000 Uani
C17 C 0.13103(6) 0.45800(17) 0.16291(12) 0.0330 1.0000 Uani
H11 H 0.3554 0.4008 0.6499 0.0354 1.0000 Uiso
H41 H 0.4523 0.5421 0.3252 0.0313 1.0000 Uiso
H51 H 0.5174 0.7432 0.3366 0.0360 1.0000 Uiso
H61 H 0.5312 0.8811 0.4972 0.0379 1.0000 Uiso
H71 H 0.4816 0.8216 0.6531 0.0365 1.0000 Uiso
H81 H 0.3981 0.3125 0.3815 0.0314 1.0000 Uiso
H82 H 0.3598 0.2476 0.4759 0.0314 1.0000 Uiso
H91 H 0.3321 0.4891 0.3291 0.0300 1.0000 Uiso
H92 H 0.2941 0.4342 0.4269 0.0300 1.0000 Uiso
H101 H 0.3299 0.2254 0.2644 0.0354 1.0000 Uiso
H102 H 0.2851 0.1887 0.3545 0.0354 1.0000 Uiso
H111 H 0.2971 0.3240 0.0883 0.0433 1.0000 Uiso
H141 H 0.1965 0.3232 0.4224 0.0346 1.0000 Uiso
H151 H 0.1052 0.4011 0.4180 0.0390 1.0000 Uiso
H161 H 0.0652 0.4858 0.2576 0.0404 1.0000 Uiso
H171 H 0.1139 0.4948 0.0961 0.0396 1.0000 Uiso
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997
0.0030 International_Tables_Vol_IV_Table_2.2B
'N ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 . N1 . C3 . 106.14(11) yes
C1 . N1 . C8 . 126.64(12) yes
C3 . N1 . C8 . 127.22(11) yes
N1 . C1 . N2 . 114.50(12) yes
N1 . C1 . H11 . 122.749 no
N2 . C1 . H11 . 122.749 no
C1 . N2 . C2 . 103.95(11) yes
N2 . C2 . C3 . 110.26(12) yes
N2 . C2 . C7 . 129.99(13) yes
C3 . C2 . C7 . 119.69(13) yes
N1 . C3 . C2 . 105.15(11) yes
N1 . C3 . C4 . 131.84(12) yes
C2 . C3 . C4 . 122.93(12) yes
C3 . C4 . C5 . 116.26(13) yes
C3 . C4 . H41 . 121.869 no
C5 . C4 . H41 . 121.869 no
C4 . C5 . C6 . 121.65(13) yes
C4 . C5 . H51 . 119.172 no
C6 . C5 . H51 . 119.173 no
C5 . C6 . C7 . 121.55(13) yes
C5 . C6 . H61 . 119.223 no
C7 . C6 . H61 . 119.223 no
C2 . C7 . C6 . 117.90(13) yes
C2 . C7 . H71 . 121.048 no
C6 . C7 . H71 . 121.048 no
N1 . C8 . C9 . 113.15(11) yes
N1 . C8 . H81 . 108.544 no
C9 . C8 . H81 . 108.544 no
N1 . C8 . H82 . 108.544 no
C9 . C8 . H82 . 108.544 no
H81 . C8 . H82 . 109.467 no
C10 . N3 . C11 . 126.78(12) yes
C10 . N3 . C13 . 127.21(12) yes
C11 . N3 . C13 . 105.94(12) yes
C8 . C9 . C10 . 108.50(11) yes
C8 . C9 . H91 . 109.715 no
C10 . C9 . H91 . 109.715 no
C8 . C9 . H92 . 109.715 no
C10 . C9 . H92 . 109.715 no
H91 . C9 . H92 . 109.467 no
C11 . N4 . C12 . 103.97(12) yes
N3 . C10 . C9 . 112.95(11) yes
N3 . C10 . H101 . 108.597 no
C9 . C10 . H101 . 108.596 no
N3 . C10 . H102 . 108.597 no
C9 . C10 . H102 . 108.596 no
H101 . C10 . H102 . 109.467 no
N3 . C11 . N4 . 114.52(13) yes
N3 . C11 . H111 . 122.740 no
N4 . C11 . H111 . 122.740 no
N4 . C12 . C13 . 110.18(12) yes
N4 . C12 . C17 . 130.29(13) yes
C13 . C12 . C17 . 119.52(13) yes
N3 . C13 . C12 . 105.39(12) yes
N3 . C13 . C14 . 131.71(12) yes
C12 . C13 . C14 . 122.90(12) yes
C13 . C14 . C15 . 116.53(13) yes
C13 . C14 . H141 . 121.737 no
C15 . C14 . H141 . 121.737 no
C14 . C15 . C16 . 121.35(14) yes
C14 . C15 . H151 . 119.325 no
C16 . C15 . H151 . 119.325 no
C15 . C16 . C17 . 121.87(13) yes
C15 . C16 . H161 . 119.065 no
C17 . C16 . H161 . 119.065 no
C12 . C17 . C16 . 117.82(13) yes
C12 . C17 . H171 . 121.090 no
C16 . C17 . H171 . 121.090 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.3613(18) yes
N1 . C3 . 1.3851(16) yes
N1 . C8 . 1.4583(17) yes
C1 . N2 . 1.3121(18) yes
C1 . H11 . 1.000 no
N2 . C2 . 1.3925(18) yes
C2 . C3 . 1.4043(18) yes
C2 . C7 . 1.394(2) yes
C3 . C4 . 1.3921(19) yes
C4 . C5 . 1.385(2) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.402(2) yes
C5 . H51 . 1.000 no
C6 . C7 . 1.383(2) yes
C6 . H61 . 1.000 no
C7 . H71 . 1.000 no
C8 . C9 . 1.5219(18) yes
C8 . H81 . 1.000 no
C8 . H82 . 1.000 no
N3 . C10 . 1.4581(18) yes
N3 . C11 . 1.3640(19) yes
N3 . C13 . 1.3833(17) yes
C9 . C10 . 1.5228(19) yes
C9 . H91 . 1.000 no
C9 . H92 . 1.000 no
N4 . C11 . 1.312(2) yes
N4 . C12 . 1.3917(19) yes
C10 . H101 . 1.000 no
C10 . H102 . 1.000 no
C11 . H111 . 1.000 no
C12 . C13 . 1.4040(19) yes
C12 . C17 . 1.398(2) yes
C13 . C14 . 1.3896(19) yes
C14 . C15 . 1.383(2) yes
C14 . H141 . 1.000 no
C15 . C16 . 1.401(2) yes
C15 . H151 . 1.000 no
C16 . C17 . 1.378(2) yes
C16 . H161 . 1.000 no
C17 . H171 . 1.000 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2990234
