#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/13/4021328.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_4021328
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         '(C22 H26 N4 O2)(Cl O4)2'
_chemical_formula_sum            'C22 H26 Cl2 N4 O10'
_chemical_formula_weight         577.37
_space_group_IT_number           9
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.49(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   17.421(3)
_cell_length_b                   14.720(2)
_cell_length_c                   20.772(4)
_cell_measurement_temperature    203(2)
_cell_volume                     5080.5(15)
_diffrn_ambient_temperature      203(2)
_exptl_crystal_density_diffrn    1.510
_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_original_sg_symbol_H-M      'C c'
_cod_database_code               4021328
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'
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 0.1204(5) 0.5282(6) 0.0222(4) 0.047(2) Uani 1 1 d U . .
N1 N 0.1803(6) 0.5068(6) 0.1495(5) 0.042(3) Uani 1 1 d U . .
H1A H 0.1765 0.5358 0.1122 0.050 Uiso 1 1 calc R . .
O2 O 0.1517(5) 0.7178(5) 0.0371(4) 0.0302(19) Uani 1 1 d U . .
N2 N 0.0498(6) 0.5508(6) -0.1030(5) 0.038(3) Uani 1 1 d U . .
H2A H 0.0866 0.5653 -0.0657 0.045 Uiso 1 1 calc R . .
N3 N 0.0910(6) 0.7391(6) -0.0909(5) 0.039(3) Uani 1 1 d U . .
H3A H 0.0932 0.7108 -0.0537 0.047 Uiso 1 1 calc R . .
N4 N 0.2273(6) 0.6948(7) 0.1615(5) 0.035(2) Uani 1 1 d U . .
H4A H 0.1897 0.6805 0.1247 0.042 Uiso 1 1 calc R . .
C101 C 0.2321(10) 0.6410(8) 0.2230(7) 0.044(4) Uani 1 1 d U . .
H10B H 0.1834 0.6508 0.2364 0.053 Uiso 1 1 calc R . .
H10C H 0.2785 0.6609 0.2601 0.053 Uiso 1 1 calc R . .
C102 C 0.2403(9) 0.5413(8) 0.2089(6) 0.045(4) Uani 1 1 d U . .
H10D H 0.2937 0.5311 0.2038 0.054 Uiso 1 1 calc R . .
H10G H 0.2372 0.5062 0.2482 0.054 Uiso 1 1 calc R . .
C103 C 0.1325(7) 0.4400(8) 0.1443(6) 0.037(3) Uani 1 1 d U . .
H10E H 0.1339 0.4071 0.1834 0.045 Uiso 1 1 calc R . .
C104 C 0.0777(7) 0.4133(8) 0.0824(6) 0.031(3) Uani 1 1 d U . .
C105 C 0.0289(9) 0.3366(8) 0.0779(7) 0.037(3) Uani 1 1 d U . .
H10A H 0.0356 0.3025 0.1175 0.044 Uiso 1 1 calc R . .
C106 C -0.0279(8) 0.3069(8) 0.0206(7) 0.036(3) Uani 1 1 d U . .
C107 C -0.0340(9) 0.3573(7) -0.0373(7) 0.036(3) Uani 1 1 d U . .
H10F H -0.0722 0.3390 -0.0777 0.043 Uiso 1 1 calc R . .
C108 C 0.0139(7) 0.4345(7) -0.0393(6) 0.030(3) Uani 1 1 d U . .
C109 C 0.0735(7) 0.4597(8) 0.0216(6) 0.033(3) Uani 1 1 d U . .
C110 C -0.0829(8) 0.2290(7) 0.0186(7) 0.041(3) Uani 1 1 d U . .
H11G H -0.0700 0.2014 0.0630 0.062 Uiso 1 1 calc R . .
H11H H -0.0765 0.1845 -0.0138 0.062 Uiso 1 1 calc R . .
H11I H -0.1381 0.2505 0.0054 0.062 Uiso 1 1 calc R . .
C111 C 0.0047(7) 0.4832(7) -0.1000(6) 0.027(2) Uani 1 1 d U . .
H11B H -0.0356 0.4654 -0.1393 0.033 Uiso 1 1 calc R . .
C112 C 0.0461(8) 0.6061(7) -0.1622(6) 0.032(3) Uani 1 1 d U . .
H11E H 0.0027 0.5832 -0.2007 0.038 Uiso 1 1 calc R . .
H11F H 0.0968 0.5993 -0.1731 0.038 Uiso 1 1 calc R . .
C113 C 0.0321(9) 0.7046(8) -0.1528(6) 0.043(3) Uani 1 1 d U . .
H11K H 0.0369 0.7389 -0.1918 0.052 Uiso 1 1 calc R . .
H11L H -0.0225 0.7132 -0.1498 0.052 Uiso 1 1 calc R . .
C114 C 0.1392(7) 0.8058(8) -0.0857(6) 0.033(3) Uani 1 1 d U . .
H11C H 0.1376 0.8385 -0.1250 0.039 Uiso 1 1 calc R . .
C115 C 0.1954(7) 0.8332(7) -0.0236(6) 0.029(3) Uani 1 1 d U . .
C116 C 0.2479(8) 0.9063(8) -0.0239(7) 0.032(3) Uani 1 1 d U . .
H11J H 0.2450 0.9362 -0.0645 0.039 Uiso 1 1 calc R . .
C117 C 0.3051(8) 0.9347(8) 0.0374(7) 0.032(3) Uani 1 1 d U . .
C118 C 0.3120(8) 0.8839(8) 0.0949(6) 0.029(3) Uani 1 1 d U . .
H11D H 0.3526 0.8989 0.1348 0.035 Uiso 1 1 calc R . .
C119 C 0.2621(8) 0.8128(8) 0.0959(6) 0.032(3) Uani 1 1 d U . .
C120 C 0.2006(7) 0.7844(7) 0.0375(6) 0.028(2) Uani 1 1 d U . .
C121 C 0.3583(8) 1.0154(9) 0.0365(7) 0.053(4) Uani 1 1 d U . .
H12C H 0.3940 1.0261 0.0817 0.079 Uiso 1 1 calc R . .
H12D H 0.3251 1.0687 0.0212 0.079 Uiso 1 1 calc R . .
H12E H 0.3899 1.0033 0.0062 0.079 Uiso 1 1 calc R . .
C122 C 0.2746(9) 0.7615(8) 0.1579(6) 0.040(3) Uani 1 1 d U . .
H12B H 0.3177 0.7768 0.1960 0.048 Uiso 1 1 calc R . .
Cl1 Cl 0.4788(2) 0.5892(2) 0.23264(15) 0.0418(9) Uani 1 1 d DU . .
O11 O 0.4959(7) 0.6545(6) 0.1892(5) 0.076(3) Uani 1 1 d DU . .
O12 O 0.4484(6) 0.5086(6) 0.1963(5) 0.075(3) Uani 1 1 d DU . .
O13 O 0.4207(5) 0.6226(6) 0.2625(4) 0.058(3) Uani 1 1 d DU . .
O14 O 0.5508(5) 0.5676(6) 0.2846(4) 0.050(3) Uani 1 1 d DU . .
Cl2 Cl 0.2927(2) 0.8716(2) 0.31971(16) 0.0458(9) Uani 1 1 d DU . .
O21 O 0.2798(7) 0.9369(7) 0.3652(5) 0.107(5) Uani 1 1 d DU . .
O22 O 0.3223(7) 0.7890(6) 0.3538(5) 0.084(4) Uani 1 1 d DU . .
O23 O 0.3495(6) 0.9044(7) 0.2880(5) 0.082(3) Uani 1 1 d DU . .
O24 O 0.2180(5) 0.8540(6) 0.2685(4) 0.060(3) Uani 1 1 d DU . .
O3 O 0.7068(5) 0.3332(5) 0.5180(4) 0.042(2) Uani 1 1 d U . .
O4 O 0.5636(6) 0.4246(5) 0.5287(4) 0.040(2) Uani 1 1 d U . .
N5 N 0.7692(7) 0.3438(6) 0.6466(5) 0.040(3) Uani 1 1 d U . .
H5A H 0.7429 0.3673 0.6078 0.048 Uiso 1 1 calc R . .
N6 N 0.6323(6) 0.3077(6) 0.3940(5) 0.042(3) Uani 1 1 d U . .
H6A H 0.6471 0.3427 0.4293 0.050 Uiso 1 1 calc R . .
N7 N 0.4997(7) 0.4137(6) 0.4020(5) 0.039(3) Uani 1 1 d U . .
H7A H 0.5225 0.3880 0.4408 0.046 Uiso 1 1 calc R . .
N8 N 0.6373(6) 0.4527(7) 0.6549(5) 0.037(3) Uani 1 1 d U . .
H8A H 0.6237 0.4176 0.6195 0.045 Uiso 1 1 calc R . .
C201 C 0.6919(8) 0.4137(9) 0.7144(7) 0.043(3) Uani 1 1 d U . .
H20F H 0.6713 0.3547 0.7233 0.051 Uiso 1 1 calc R . .
H20G H 0.6956 0.4533 0.7531 0.051 Uiso 1 1 calc R . .
C202 C 0.7770(8) 0.4012(9) 0.7062(6) 0.040(3) Uani 1 1 d U . .
H20D H 0.7997 0.4604 0.7003 0.048 Uiso 1 1 calc R . .
H20E H 0.8129 0.3723 0.7466 0.048 Uiso 1 1 calc R . .
C203 C 0.7972(7) 0.2614(9) 0.6451(6) 0.035(3) Uani 1 1 d U . .
H20C H 0.8291 0.2346 0.6854 0.042 Uiso 1 1 calc R . .
C204 C 0.7798(7) 0.2110(8) 0.5828(6) 0.032(3) Uani 1 1 d U . .
C205 C 0.8100(8) 0.1226(8) 0.5856(7) 0.039(3) Uani 1 1 d U . .
H20B H 0.8433 0.0998 0.6268 0.047 Uiso 1 1 calc R . .
C206 C 0.7914(9) 0.0677(8) 0.5283(7) 0.040(3) Uani 1 1 d U . .
C207 C 0.7440(8) 0.1054(8) 0.4672(7) 0.036(3) Uani 1 1 d U . .
H20A H 0.7321 0.0698 0.4278 0.043 Uiso 1 1 calc R . .
C208 C 0.7141(8) 0.1939(8) 0.4628(6) 0.034(3) Uani 1 1 d U . .
C209 C 0.7312(8) 0.2511(8) 0.5212(6) 0.036(3) Uani 1 1 d U . .
C210 C 0.8217(9) -0.0295(8) 0.5312(7) 0.052(4) Uani 1 1 d U . .
H21J H 0.8033 -0.0563 0.4865 0.077 Uiso 1 1 calc R . .
H21K H 0.8011 -0.0646 0.5620 0.077 Uiso 1 1 calc R . .
H21L H 0.8801 -0.0298 0.5470 0.077 Uiso 1 1 calc R . .
C211 C 0.6608(8) 0.2253(8) 0.3997(6) 0.040(3) Uani 1 1 d U . .
H21G H 0.6463 0.1861 0.3623 0.048 Uiso 1 1 calc R . .
C212 C 0.5764(8) 0.3455(8) 0.3315(6) 0.036(3) Uani 1 1 d U . .
H21C H 0.5715 0.3035 0.2938 0.043 Uiso 1 1 calc R . .
H21D H 0.5973 0.4035 0.3205 0.043 Uiso 1 1 calc R . .
C213 C 0.4954(9) 0.3599(9) 0.3417(6) 0.044(3) Uani 1 1 d U . .
H21H H 0.4600 0.3908 0.3020 0.053 Uiso 1 1 calc R . .
H21I H 0.4715 0.3006 0.3455 0.053 Uiso 1 1 calc R . .
C214 C 0.4738(8) 0.4932(8) 0.4035(6) 0.039(3) Uani 1 1 d U . .
H21F H 0.4444 0.5204 0.3626 0.047 Uiso 1 1 calc R . .
C215 C 0.4865(8) 0.5433(8) 0.4633(6) 0.036(3) Uani 1 1 d U . .
C216 C 0.4578(9) 0.6339(8) 0.4617(7) 0.037(3) Uani 1 1 d U . .
H21E H 0.4261 0.6579 0.4203 0.044 Uiso 1 1 calc R . .
C217 C 0.4746(8) 0.6882(8) 0.5187(7) 0.037(3) Uani 1 1 d U . .
C218 C 0.5230(8) 0.6519(8) 0.5762(7) 0.032(3) Uani 1 1 d U . .
H21B H 0.5360 0.6892 0.6147 0.039 Uiso 1 1 calc R . .
C219 C 0.5555(8) 0.5652(8) 0.5843(6) 0.034(3) Uani 1 1 d U . .
C220 C 0.5362(8) 0.5062(7) 0.5255(6) 0.033(3) Uani 1 1 d U . .
C221 C 0.4441(9) 0.7841(8) 0.5150(6) 0.050(4) Uani 1 1 d U . .
H22B H 0.4621 0.8115 0.5595 0.074 Uiso 1 1 calc R . .
H22C H 0.3858 0.7840 0.4989 0.074 Uiso 1 1 calc R . .
H22D H 0.4648 0.8188 0.4841 0.074 Uiso 1 1 calc R . .
C222 C 0.6054(7) 0.5333(8) 0.6465(6) 0.034(3) Uani 1 1 d U . .
H22E H 0.6163 0.5722 0.6841 0.040 Uiso 1 1 calc R . .
Cl3 Cl 0.2602(2) 0.3163(2) 0.31966(16) 0.0480(9) Uani 1 1 d DU . .
O31 O 0.3086(7) 0.3510(8) 0.2808(6) 0.124(5) Uani 1 1 d DU . .
O32 O 0.2941(6) 0.2330(6) 0.3508(5) 0.088(4) Uani 1 1 d DU . .
O33 O 0.1817(5) 0.2995(6) 0.2758(4) 0.064(3) Uani 1 1 d DU . .
O34 O 0.2560(8) 0.3811(8) 0.3685(5) 0.122(5) Uani 1 1 d DU . .
Cl4 Cl 0.0076(2) 0.6101(2) 0.22987(17) 0.0491(9) Uani 1 1 d DU . .
O41 O -0.0407(6) 0.5353(6) 0.2007(5) 0.079(4) Uani 1 1 d DU . .
O42 O 0.0263(7) 0.6643(8) 0.1826(5) 0.127(5) Uani 1 1 d DU . .
O43 O -0.0351(7) 0.6615(8) 0.2663(6) 0.126(5) Uani 1 1 d DU . .
O44 O 0.0802(5) 0.5809(6) 0.2789(4) 0.056(3) Uani 1 1 d DU . .
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 C109 1.295(12) . ?
N1 C103 1.272(13) . ?
N1 C102 1.448(14) . ?
O2 C120 1.298(12) . ?
N2 C111 1.279(13) . ?
N2 C112 1.460(13) . ?
N3 C114 1.275(13) . ?
N3 C113 1.473(14) . ?
N4 C122 1.298(15) . ?
N4 C101 1.484(15) . ?
C101 C102 1.512(16) . ?
C103 C104 1.407(16) . ?
C104 C105 1.399(16) . ?
C104 C109 1.420(16) . ?
C105 C106 1.371(18) . ?
C106 C107 1.390(18) . ?
C106 C110 1.487(16) . ?
C107 C108 1.417(16) . ?
C108 C111 1.419(15) . ?
C108 C109 1.422(16) . ?
C112 C113 1.493(15) . ?
C114 C115 1.424(15) . ?
C115 C116 1.413(17) . ?
C115 C120 1.437(15) . ?
C116 C117 1.423(18) . ?
C117 C118 1.383(17) . ?
C117 C121 1.511(16) . ?
C118 C119 1.364(17) . ?
C119 C120 1.420(16) . ?
C119 C122 1.451(16) . ?
Cl1 O11 1.410(8) . ?
Cl1 O12 1.420(8) . ?
Cl1 O13 1.423(8) . ?
Cl1 O14 1.424(8) . ?
Cl2 O21 1.413(8) . ?
Cl2 O22 1.424(8) . ?
Cl2 O23 1.428(9) . ?
Cl2 O24 1.436(8) . ?
O3 C209 1.276(12) . ?
O4 C220 1.287(12) . ?
N5 C203 1.312(14) . ?
N5 C202 1.472(15) . ?
N6 C211 1.302(14) . ?
N6 C212 1.479(14) . ?
N7 C214 1.258(14) . ?
N7 C213 1.465(14) . ?
N8 C222 1.299(14) . ?
N8 C201 1.434(15) . ?
C201 C202 1.552(19) . ?
C203 C204 1.443(16) . ?
C204 C205 1.398(16) . ?
C204 C209 1.432(16) . ?
C205 C206 1.394(18) . ?
C206 C207 1.404(18) . ?
C206 C210 1.521(15) . ?
C207 C208 1.396(16) . ?
C208 C209 1.433(16) . ?
C208 C211 1.435(16) . ?
C212 C213 1.505(18) . ?
C214 C215 1.404(17) . ?
C215 C216 1.421(16) . ?
C215 C220 1.429(16) . ?
C216 C217 1.384(18) . ?
C217 C218 1.349(17) . ?
C217 C221 1.503(16) . ?
C218 C219 1.385(16) . ?
C219 C222 1.404(16) . ?
C219 C220 1.454(16) . ?
Cl3 O34 1.411(8) . ?
Cl3 O33 1.419(8) . ?
Cl3 O31 1.426(9) . ?
Cl3 O32 1.428(8) . ?
Cl4 O42 1.379(8) . ?
Cl4 O41 1.407(8) . ?
Cl4 O43 1.427(9) . ?
Cl4 O44 1.431(8) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658511
