#------------------------------------------------------------------------------
#$Date: 2015-01-27 21:58:39 +0200 (Tue, 27 Jan 2015) $
#$Revision: 130149 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021329.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_4021329
loop_
_publ_author_name
'Bula Dutta'
'Pradip Bag'
'Bibhutosh Adhikary'
'Ulrich Flörke'
'Kamalaksha Nag'
_publ_section_title
;
 Efficient Proton-Templated Synthesis of 18- to 38-Membered
 Tetraimino(amino)diphenol Macrocyclic Ligands:
 Structural Features and Spectroscopic Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5419
_journal_page_last               5427
_journal_paper_doi               10.1021/jo049787s
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         '(C26 H34 N4 O)(Cl O4)2'
_chemical_formula_sum            'C26 H34 Cl2 N4 O10'
_chemical_formula_weight         633.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                94.63(9)
_cell_angle_beta                 100.47(9)
_cell_angle_gamma                106.95(4)
_cell_formula_units_Z            1
_cell_length_a                   7.655(5)
_cell_length_b                   8.912(4)
_cell_length_c                   11.204(12)
_cell_measurement_temperature    203(2)
_cell_volume                     711.7(9)
_diffrn_ambient_temperature      203(2)
_exptl_crystal_density_diffrn    1.478
_cod_database_code               4021329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.2711(4) 0.2228(3) 0.9725(3) 0.0443(7) Uani 1 1 d . . .
N1 N 0.1933(5) 0.1926(4) 1.1862(3) 0.0434(8) Uani 1 1 d . . .
H1 H 0.2107 0.2484 1.1267 0.052 Uiso 1 1 calc R . .
N2 N 0.3563(5) 0.2342(4) 0.7590(3) 0.0455(9) Uani 1 1 d . . .
H2 H 0.3275 0.2775 0.8219 0.055 Uiso 1 1 calc R . .
C1 C 0.4149(6) 0.5250(5) 1.2708(4) 0.0435(9) Uani 1 1 d . . .
H1A H 0.4415 0.4715 1.1996 0.052 Uiso 1 1 calc R . .
H1B H 0.3110 0.5653 1.2414 0.052 Uiso 1 1 calc R . .
C2 C 0.3564(6) 0.4058(5) 1.3572(4) 0.0420(9) Uani 1 1 d . . .
H2A H 0.4565 0.3592 1.3812 0.050 Uiso 1 1 calc R . .
H2B H 0.3404 0.4613 1.4316 0.050 Uiso 1 1 calc R . .
C3 C 0.1766(6) 0.2743(5) 1.3006(4) 0.0474(10) Uani 1 1 d . . .
H3A H 0.1486 0.1983 1.3584 0.057 Uiso 1 1 calc R . .
H3B H 0.0732 0.3189 1.2838 0.057 Uiso 1 1 calc R . .
C4 C 0.1847(5) 0.0464(5) 1.1657(4) 0.0414(9) Uani 1 1 d . . .
H4A H 0.1570 -0.0185 1.2262 0.050 Uiso 1 1 calc R . .
C5 C 0.2157(5) -0.0219(4) 1.0536(4) 0.0395(9) Uani 1 1 d . . .
C6 C 0.2048(5) -0.1808(5) 1.0383(4) 0.0433(9) Uani 1 1 d . . .
H6A H 0.1737 -0.2414 1.1007 0.052 Uiso 1 1 calc R . .
C7 C 0.2383(6) -0.2538(5) 0.9337(4) 0.0447(10) Uani 1 1 d . . .
C8 C 0.2835(6) -0.1608(5) 0.8429(4) 0.0445(10) Uani 1 1 d . . .
H8A H 0.3067 -0.2079 0.7718 0.053 Uiso 1 1 calc R . .
C9 C 0.2959(5) -0.0009(5) 0.8528(4) 0.0404(9) Uani 1 1 d . . .
C10 C 0.2610(5) 0.0754(4) 0.9604(3) 0.0375(8) Uani 1 1 d . . .
C11 C 0.2282(7) -0.4249(5) 0.9202(5) 0.0559(12) Uani 1 1 d . . .
H11A H 0.1948 -0.4699 0.9920 0.084 Uiso 0.50 1 calc PR . .
H11B H 0.3489 -0.4338 0.9119 0.084 Uiso 0.50 1 calc PR . .
H11C H 0.1343 -0.4818 0.8478 0.084 Uiso 0.50 1 calc PR . .
H11D H 0.2572 -0.4538 0.8424 0.084 Uiso 0.50 1 calc PR . .
H11E H 0.1031 -0.4899 0.9225 0.084 Uiso 0.50 1 calc PR . .
H11F H 0.3177 -0.4419 0.9867 0.084 Uiso 0.50 1 calc PR . .
C12 C 0.3442(6) 0.0868(5) 0.7552(4) 0.0436(9) Uani 1 1 d . . .
H12A H 0.3677 0.0349 0.6863 0.052 Uiso 1 1 calc R . .
C13 C 0.4136(6) 0.3363(5) 0.6680(4) 0.0464(10) Uani 1 1 d . . .
H13A H 0.3114 0.3757 0.6328 0.056 Uiso 1 1 calc R . .
H13B H 0.4425 0.2757 0.6016 0.056 Uiso 1 1 calc R . .
Cl1 Cl 0.16542(19) 0.77910(17) 0.43641(12) 0.0651(5) Uani 1 1 d D . .
O11 O 0.2652(9) 0.7303(7) 0.5329(4) 0.131(2) Uani 1 1 d DU A .
O121 O 0.085(2) 0.8851(18) 0.4658(16) 0.134(8) Uani 0.50 1 d PDU A 1
O131 O 0.031(2) 0.6367(18) 0.3720(16) 0.207(12) Uani 0.50 1 d PDU A 1
O141 O 0.2832(19) 0.8285(19) 0.3559(12) 0.111(5) Uani 0.50 1 d PDU A 1
O122 O 0.033(2) 0.834(2) 0.4798(15) 0.148(9) Uani 0.50 1 d PDU A 2
O132 O 0.096(2) 0.688(2) 0.3293(9) 0.184(11) Uani 0.50 1 d PDU A 2
O142 O 0.302(2) 0.924(2) 0.4194(17) 0.212(12) Uani 0.50 1 d PDU A 2
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
O1 C10 1.288(5) . ?
N1 C4 1.285(5) . ?
N1 C3 1.468(5) . ?
N2 C12 1.287(5) . ?
N2 C13 1.462(5) . ?
C1 C13 1.520(6) 2_667 ?
C1 C2 1.520(6) . ?
C2 C3 1.514(6) . ?
C4 C5 1.440(6) . ?
C5 C6 1.389(6) . ?
C5 C10 1.437(6) . ?
C6 C7 1.395(6) . ?
C7 C8 1.393(6) . ?
C7 C11 1.498(6) . ?
C8 C9 1.395(6) . ?
C9 C12 1.435(6) . ?
C9 C10 1.441(6) . ?
C13 C1 1.520(6) 2_667 ?
Cl1 O132 1.321(9) . ?
Cl1 O121 1.321(8) . ?
Cl1 O11 1.382(5) . ?
Cl1 O122 1.389(11) . ?
Cl1 O141 1.396(9) . ?
Cl1 O131 1.418(11) . ?
Cl1 O142 1.455(11) . ?
