#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/76/4317618.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_4317618
loop_
_publ_author_name
'Christopher B. Smith'
'Ashley K. W. Stephens'
'Kia S. Wallwork'
'Stephen F. Lincoln'
'Max R. Taylor'
'Kevin P. Wainwright'
_publ_contact_author_address
;
School of Chemistry,
The Flinders University of South Australia,
GPO Box 2100,
Adelaide, SA 5001
Australia
;
_publ_contact_author_email       kevin.wainwright@flinders.edu.au
_publ_contact_author_fax         '+61 8 8201 2905'
_publ_contact_author_name        'Wainwright, K, P.'
_publ_contact_author_phone       '+61 8 8201 2268'
_publ_section_title
;
 Metal Ion-Dependent Molecular Inclusion Chemistry: Inclusion of Aromatic
 Anions by Coordinated
 1,4,7,10-Tetrakis((S)-2-hydroxy-3-phenoxypropyl)-1,4,7,10-tetraazacyclododecane
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1093
_journal_page_last               1100
_journal_paper_doi               10.1021/ic010694s
_journal_volume                  41
_journal_year                    2002
_chemical_formula_iupac          '[Cd (C44 H60 N4 O8)(C7 H6 N O2)]Cl O4'
_chemical_formula_moiety         'C44 H60 N4 O8 Cd, C7 H6 N O2, Cl O4'
_chemical_formula_sum            'C51 H66 Cd Cl N5 O14'
_chemical_formula_weight         1120.97
_chemical_name_systematic
;
[1,4,7,10-tetrakis((S)-2-hydroxy-3-phenoxypropyl)
-1,4,7,10-tetraazacyclododecanecadmium(II)
(p-aminobenzoate)] ClO4
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_cell_angle_alpha                111.50(4)
_cell_angle_beta                 91.10(3)
_cell_angle_gamma                115.76(3)
_cell_formula_units_Z            1
_cell_length_a                   10.561(3)
_cell_length_b                   11.823(4)
_cell_length_c                   12.284(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    150
_cell_measurement_theta_max      18
_cell_measurement_theta_min      15
_cell_volume                     1255.8(10)
_computing_data_reduction        'xtal DIFDAT ABSORB SORTRF ADDREF'
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      150
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_sigmaI/netI    .07
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8766
_diffrn_reflns_theta_max         25.13
_diffrn_reflns_theta_min         2.1
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.56
_exptl_absorpt_correction_T_max  0.914
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'ABSORB (Hall,  King & Stewart (1995)).'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       irregular
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.98
_refine_ls_abs_structure_details 'Flack xabs refined'
_refine_ls_abs_structure_Flack   -.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.46
_refine_ls_goodness_of_fit_ref   1.46
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     647
_refine_ls_number_reflns         4379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          .024
_refine_ls_R_factor_gt           .024
_refine_ls_shift/su_max          0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     'w = 1/σ²(Fsqd)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         .074
_refine_ls_wR_factor_ref         .074
_reflns_d_resolution_high        .837
_reflns_d_resolution_low         9.682
_reflns_Friedel_coverage         99
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              12
_reflns_limit_k_min              -14
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                4377
_reflns_number_total             4381
_reflns_threshold_expression     'Fsqd >  .00 sig(Fsqd)'
_cod_data_source_file            ic010694s_2.cif
_cod_data_source_block           kia8
_cod_original_cell_volume        1255.7(10)
_cod_original_sg_symbol_Hall     p_1
_cod_original_formula_sum        'C51 H66 Cd1 Cl1 N5 O14'
_cod_database_code               4317618
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cd .01161 .02467 .00366 .01616(10) Uani ? ? 1.00000 ? ?
C1 -.2788(5) -.2612(4) -.1619(4) .0231(15) Uani ? ? 1.00000 ? ?
C2 -.2682(5) -.1698(5) -.2250(4) .0243(15) Uani ? ? 1.00000 ? ?
C3 -.2921(5) .0136(5) -.0704(4) .0227(15) Uani ? ? 1.00000 ? ?
C4 -.2156(5) .1495(5) .0407(4) .0222(15) Uani ? ? 1.00000 ? ?
C5 -.1800(4) .0791(5) .1969(4) .0219(14) Uani ? ? 1.00000 ? ?
C6 -.0841(5) .0384(4) .2523(4) .0223(14) Uani ? ? 1.00000 ? ?
C7 -.1692(5) -.1972(5) .1036(4) .0227(15) Uani ? ? 1.00000 ? ?
C8 -.1515(5) -.2870(4) -.0126(4) .0221(15) Uani ? ? 1.00000 ? ?
C11 -.0666(5) -.2919(4) -.1931(4) .0235(17) Uani ? ? 1.00000 ? ?
C12 .0967(5) -.2089(5) -.1496(4) .0237(17) Uani ? ? 1.00000 ? ?
C13 .1746(6) -.2725(5) -.2317(5) .0332(18) Uani ? ? 1.00000 ? ?
C14 .3540(5) -.2653(5) -.1023(5) .0305(17) Uani ? ? 1.00000 ? ?
C15 .4023(5) -.1872(5) .0218(5) .0357(19) Uani ? ? 1.00000 ? ?
C16 .4435(6) -.2395(7) .0911(6) .044(2) Uani ? ? 1.00000 ? ?
C17 .4356(6) -.3682(7) .0405(6) .044(2) Uani ? ? 1.00000 ? ?
C18 .3841(6) -.4474(6) -.0829(5) .040(2) Uani ? ? 1.00000 ? ?
C19 .3440(5) -.3960(6) -.1545(5) .035(2) Uani ? ? 1.00000 ? ?
C21 -.1377(5) .0643(5) -.2078(4) .0217(16) Uani ? ? 1.00000 ? ?
C22 .0056(5) .0806(4) -.2336(4) .0219(15) Uani ? ? 1.00000 ? ?
C23 .0478(5) .1569(5) -.3132(4) .0248(15) Uani ? ? 1.00000 ? ?
C24 .2606(6) .2604(5) -.3807(4) .0300(17) Uani ? ? 1.00000 ? ?
C25 .1905(7) .3034(7) -.4433(5) .044(2) Uani ? ? 1.00000 ? ?
C26 .2750(10) .3931(10) -.4918(6) .071(3) Uani ? ? 1.00000 ? ?
C27 .4223(8) .4407(7) -.4776(6) .064(3) Uani ? ? 1.00000 ? ?
C28 .4866(7) .3944(6) -.4178(6) .054(2) Uani ? ? 1.00000 ? ?
C29 .4071(6) .3049(5) -.3667(5) .040(2) Uani ? ? 1.00000 ? ?
C31 -.0014(5) .3002(5) .2051(4) .0205(15) Uani ? ? 1.00000 ? ?
C32 .1309(5) .3528(5) .1559(4) .0205(15) Uani ? ? 1.00000 ? ?
C33 .2470(5) .4958(4) .2456(4) .0207(14) Uani ? ? 1.00000 ? ?
C34 .2484(5) .7053(4) .3747(4) .0231(14) Uani ? ? 1.00000 ? ?
C35 .1596(6) .7629(5) .4133(4) .0330(17) Uani ? ? 1.00000 ? ?
C36 .2096(6) .8799(6) .5232(5) .039(2) Uani ? ? 1.00000 ? ?
C37 .3449(6) .9370(5) .5929(4) .0368(19) Uani ? ? 1.00000 ? ?
C38 .4328(6) .8784(6) .5514(5) .035(2) Uani ? ? 1.00000 ? ?
C39 .3857(6) .7631(5) .4432(5) .0331(18) Uani ? ? 1.00000 ? ?
C41 .0791(6) -.0573(5) .2217(4) .0235(16) Uani ? ? 1.00000 ? ?
C42 .2233(5) .0608(5) .2312(4) .0224(16) Uani ? ? 1.00000 ? ?
C43 .3457(5) .0608(5) .3000(4) .0270(16) Uani ? ? 1.00000 ? ?
C44 .6005(5) .2192(5) .3768(4) .0284(16) Uani ? ? 1.00000 ? ?
C45 .7113(5) .3476(6) .3918(5) .0336(18) Uani ? ? 1.00000 ? ?
C46 .8410(6) .4080(6) .4732(6) .044(2) Uani ? ? 1.00000 ? ?
C47 .8618(6) .3414(7) .5384(5) .049(2) Uani ? ? 1.00000 ? ?
C48 .7518(7) .2129(7) .5217(5) .045(2) Uani ? ? 1.00000 ? ?
C49 .6209(6) .1510(6) .4398(5) .031(2) Uani ? ? 1.00000 ? ?
N1 -.1350(4) -.2305(4) -.1044(4) .0208(14) Uani ? ? 1.00000 ? ?
N2 -.1930(4) -.0213(4) -.1396(4) .0206(14) Uani ? ? 1.00000 ? ?
N3 -.1080(4) .1541(4) .1249(4) .0189(13) Uani ? ? 1.00000 ? ?
N4 -.0437(4) -.0553(4) .1618(3) .0187(14) Uani ? ? 1.00000 ? ?
O12 .1319(4) -.0750(4) -.1419(3) .0245(12) Uani ? ? 1.00000 ? ?
O13 .3237(4) -.2079(4) -.1733(3) .0351(13) Uani ? ? 1.00000 ? ?
O22 .1066(4) .1580(4) -.1202(3) .0218(12) Uani ? ? 1.00000 ? ?
O23 .1883(4) .1760(4) -.3272(3) .0304(12) Uani ? ? 1.00000 ? ?
O32 .1847(3) .2570(3) .1384(3) .0212(12) Uani ? ? 1.00000 ? ?
O33 .1901(4) .5894(3) .2651(3) .0274(11) Uani ? ? 1.00000 ? ?
O42 .2378(4) .0385(3) .1107(3) .0229(12) Uani ? ? 1.00000 ? ?
O43 .4763(4) .1699(4) .2964(3) .0360(14) Uani ? ? 1.00000 ? ?
Cl -.24093(15) -.25225(14) .42710(13) .0391(5) Uani ? ? 1.00000 ? ?
O1 -.1298(6) -.2122(8) .3687(6) .081(3) Uani ? ? 1.00000 ? ?
O2 -.2615(6) -.1395(6) .5006(5) .070(2) Uani ? ? 1.00000 ? ?
O3 -.1978(11) -.3028(9) .5057(7) .103(4) Uani ? ? 1.00000 ? ?
O4 -.3704(6) -.3576(8) .3438(8) .127(3) Uani ? ? 1.00000 ? ?
N5 1.0596(5) .5519(5) .0076(5) .0360(18) Uani ? ? 1.00000 ? ?
O5 .3714(4) .1597(4) -.1209(3) .0361(12) Uani ? ? 1.00000 ? ?
O6 .4196(4) .2783(4) .0777(3) .0368(13) Uani ? ? 1.00000 ? ?
C01 .9128(6) .4738(6) -.0015(5) .0253(17) Uani ? ? 1.00000 ? ?
C02 .8167(5) .3744(5) -.1120(4) .0236(15) Uani ? ? 1.00000 ? ?
C03 .6695(5) .3024(4) -.1187(4) .0229(15) Uani ? ? 1.00000 ? ?
C04 .6150(5) .3293(4) -.0165(4) .0207(15) Uani ? ? 1.00000 ? ?
C05 .7100(5) .4318(5) .0933(4) .0239(16) Uani ? ? 1.00000 ? ?
C06 .8569(5) .5020(5) .1009(4) .0247(15) Uani ? ? 1.00000 ? ?
C07 .4579(5) .2504(5) -.0206(4) .0233(15) Uani ? ? 1.00000 ? ?
H421' .30030 .11040 .11760 .04000 Uiso ? ? 1.00000 ? ?
H321' .26070 .28410 .10900 .04000 Uiso ? ? 1.00000 ? ?
H221' .19960 .16470 -.13330 .04000 Uiso ? ? 1.00000 ? ?
H121' .22230 -.02080 -.11730 .04000 Uiso ? ? 1.00000 ? ?
H11 -.33256 -.24966 -.10244 .04000 Uiso ? ? 1.00000 ? ?
H12 -.32896 -.35836 -.21932 .04000 Uiso ? ? 1.00000 ? ?
H21 -.36288 -.19562 -.26247 .04000 Uiso ? ? 1.00000 ? ?
H22 -.21704 -.18749 -.28955 .04000 Uiso ? ? 1.00000 ? ?
H31 -.34648 -.06050 -.04818 .04000 Uiso ? ? 1.00000 ? ?
H32 -.35671 .01770 -.12266 .04000 Uiso ? ? 1.00000 ? ?
H41 -.28578 .16227 .07974 .04000 Uiso ? ? 1.00000 ? ?
H42 -.16733 .21913 .01281 .04000 Uiso ? ? 1.00000 ? ?
H51 -.26498 -.00572 .14405 .04000 Uiso ? ? 1.00000 ? ?
H52 -.20705 .13295 .25654 .04000 Uiso ? ? 1.00000 ? ?
H61 -.13337 -.00711 .29944 .04000 Uiso ? ? 1.00000 ? ?
H62 .00183 .11865 .29929 .04000 Uiso ? ? 1.00000 ? ?
H71 -.25302 -.19119 .08693 .04000 Uiso ? ? 1.00000 ? ?
H72 -.18069 -.24150 .15636 .04000 Uiso ? ? 1.00000 ? ?
H81 -.23311 -.37816 -.04561 .04000 Uiso ? ? 1.00000 ? ?
H82 -.06755 -.29745 .00104 .04000 Uiso ? ? 1.00000 ? ?
H111 -.09062 -.29118 -.27009 .04000 Uiso ? ? 1.00000 ? ?
H112 -.09758 -.38758 -.20959 .04000 Uiso ? ? 1.00000 ? ?
H211 -.13131 .14962 -.16452 .04000 Uiso ? ? 1.00000 ? ?
H212 -.20718 .01808 -.28368 .04000 Uiso ? ? 1.00000 ? ?
H311 .02437 .30042 .27897 .04000 Uiso ? ? 1.00000 ? ?
H312 -.04669 .35341 .21154 .04000 Uiso ? ? 1.00000 ? ?
H411 .07904 -.14505 .17481 .04000 Uiso ? ? 1.00000 ? ?
H412 .06754 -.05267 .29793 .04000 Uiso ? ? 1.00000 ? ?
H131 .16894 -.26015 -.30479 .04000 Uiso ? ? 1.00000 ? ?
H132 .12991 -.37081 -.25414 .04000 Uiso ? ? 1.00000 ? ?
H231 .04887 .24109 -.28027 .04000 Uiso ? ? 1.00000 ? ?
H232 -.01752 .10116 -.39220 .04000 Uiso ? ? 1.00000 ? ?
H331 .33049 .52266 .21046 .04000 Uiso ? ? 1.00000 ? ?
H332 .27117 .49009 .31593 .04000 Uiso ? ? 1.00000 ? ?
H431 .34371 -.02891 .25981 .04000 Uiso ? ? 1.00000 ? ?
H432 .33465 .07442 .37761 .04000 Uiso ? ? 1.00000 ? ?
H121 .12456 -.21022 -.07682 .04000 Uiso ? ? 1.00000 ? ?
H221 .00331 -.00842 -.27695 .04000 Uiso ? ? 1.00000 ? ?
H321 .10884 .35733 .08197 .04000 Uiso ? ? 1.00000 ? ?
H421 .23005 .14659 .27131 .04000 Uiso ? ? 1.00000 ? ?
H02 .85295 .35329 -.18610 .04000 Uiso ? ? 1.00000 ? ?
H03 .60562 .23239 -.19569 .04000 Uiso ? ? 1.00000 ? ?
H05 .67231 .45006 .16137 .04000 Uiso ? ? 1.00000 ? ?
H06 .91873 .56652 .17469 .04000 Uiso ? ? 1.00000 ? ?
H15 .40695 -.10131 .05461 .06000 Uiso ? ? 1.00000 ? ?
H16 .47530 -.19108 .17438 .06000 Uiso ? ? 1.00000 ? ?
H17 .46399 -.40683 .08560 .06000 Uiso ? ? 1.00000 ? ?
H18 .37642 -.54094 -.12008 .06000 Uiso ? ? 1.00000 ? ?
H19 .31196 -.45067 -.24220 .06000 Uiso ? ? 1.00000 ? ?
H25 .08892 .26628 -.45527 .06000 Uiso ? ? 1.00000 ? ?
H26 .22976 .42065 -.53605 .06000 Uiso ? ? 1.00000 ? ?
H27 .47853 .50306 -.51041 .06000 Uiso ? ? 1.00000 ? ?
H28 .58830 .42210 -.41242 .06000 Uiso ? ? 1.00000 ? ?
H29 .45197 .27253 -.32403 .06000 Uiso ? ? 1.00000 ? ?
H35 .06456 .72043 .36205 .06000 Uiso ? ? 1.00000 ? ?
H36 .15107 .92040 .54930 .06000 Uiso ? ? 1.00000 ? ?
H37 .37691 1.01069 .66535 .06000 Uiso ? ? 1.00000 ? ?
H38 .52726 .91509 .59558 .06000 Uiso ? ? 1.00000 ? ?
H39 .44825 .72116 .41222 .06000 Uiso ? ? 1.00000 ? ?
H45 .69709 .38980 .34341 .06000 Uiso ? ? 1.00000 ? ?
H46 .91679 .49411 .48144 .06000 Uiso ? ? 1.00000 ? ?
H47 .95085 .38021 .59273 .06000 Uiso ? ? 1.00000 ? ?
H48 .76078 .16351 .56594 .06000 Uiso ? ? 1.00000 ? ?
H49 .54801 .05894 .42498 .06000 Uiso ? ? 1.00000 ? ?
H51' 1.11300 .57300 .08300 .07000 Uiso ? ? 1.00000 ? ?
H52' 1.09100 .49600 -.06000 .07000 Uiso ? ? 1.00000 ? ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_oxidation_number
_atom_type_number_in_cell
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O ? 0 14 .008 .006 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N ? 0 5 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1'
C ? 0 51 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 66 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Cd ? 0 1 -1.005 1.202 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Cl ? 0 1 .132 .159 'Int Tables Vol IV Tables 2.2B and 2.3.1'
loop_
_diffrn_attenuator_code
_diffrn_attenuator_scale
? ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O6 H421' O42 . . . 159.4 ?
O6 H321' O32 . . . 149.5 ?
O5 H221' O22 . . . 162.4 ?
O5 H121' O12 . . . 138.1 ?
O32 Cd N4 . . . 94.24(12) ?
O32 Cd O12 . . . 108.87(11) ?
O32 Cd N1 . . . 165.53(16) ?
O32 Cd N2 . . . 121.25(15) ?
O32 Cd N3 . . . 68.45(12) ?
O32 Cd O22 . . . 72.69(12) ?
O32 Cd O42 . . . 67.00(13) ?
N4 Cd O12 . . . 117.13(17) ?
N4 Cd N1 . . . 75.56(14) ?
N4 Cd N2 . . . 117.87(14) ?
N4 Cd N3 . . . 75.26(17) ?
N4 Cd O22 . . . 166.93(9) ?
N4 Cd O42 . . . 68.90(14) ?
O12 Cd N1 . . . 68.29(13) ?
O12 Cd N2 . . . 98.57(14) ?
O12 Cd N3 . . . 167.61(17) ?
O12 Cd O22 . . . 68.73(15) ?
O12 Cd O42 . . . 68.56(13) ?
N1 Cd N2 . . . 73.06(16) ?
N1 Cd N3 . . . 117.42(13) ?
N1 Cd O22 . . . 117.29(13) ?
N1 Cd O42 . . . 99.37(14) ?
N2 Cd N3 . . . 73.96(14) ?
N2 Cd O22 . . . 70.72(14) ?
N2 Cd O42 . . . 167.00(13) ?
N3 Cd O22 . . . 99.19(16) ?
N3 Cd O42 . . . 119.04(13) ?
O22 Cd O42 . . . 104.86(13) ?
H11 C1 H12 . . . 107.7 ?
H11 C1 N1 . . . 108.4 ?
H11 C1 C2 . . . 109.8 ?
H12 C1 N1 . . . 108.3 ?
H12 C1 C2 . . . 109.8 ?
N1 C1 C2 . . . 112.7(4) ?
H21 C2 H22 . . . 106.4 ?
H21 C2 N2 . . . 110.7 ?
H21 C2 C1 . . . 109.4 ?
H22 C2 N2 . . . 110.8 ?
H22 C2 C1 . . . 108.5 ?
N2 C2 C1 . . . 111.0(4) ?
H32 C3 H31 . . . 108.4 ?
H32 C3 N2 . . . 107.1 ?
H32 C3 C4 . . . 110.5 ?
H31 C3 N2 . . . 107.6 ?
H31 C3 C4 . . . 110.2 ?
N2 C3 C4 . . . 113.0(3) ?
H41 C4 H42 . . . 111.4 ?
H41 C4 N3 . . . 109.3 ?
H41 C4 C3 . . . 107.1 ?
H42 C4 N3 . . . 108.8 ?
H42 C4 C3 . . . 106.2 ?
N3 C4 C3 . . . 114.0(5) ?
H52 C5 H51 . . . 109.8 ?
H52 C5 N3 . . . 109.3 ?
H52 C5 C6 . . . 109.7 ?
H51 C5 N3 . . . 107.9 ?
H51 C5 C6 . . . 107.7 ?
N3 C5 C6 . . . 112.4(4) ?
H62 C6 H61 . . . 110.6 ?
H62 C6 N4 . . . 107.1 ?
H62 C6 C5 . . . 109.0 ?
H61 C6 N4 . . . 107.5 ?
H61 C6 C5 . . . 109.6 ?
N4 C6 C5 . . . 113.0(4) ?
H71 C7 H72 . . . 109.9 ?
H71 C7 N4 . . . 109.6 ?
H71 C7 C8 . . . 107.6 ?
H72 C7 N4 . . . 109.0 ?
H72 C7 C8 . . . 107.5 ?
N4 C7 C8 . . . 113.3(4) ?
H81 C8 H82 . . . 107.1 ?
H81 C8 N1 . . . 108.1 ?
H81 C8 C7 . . . 110.5 ?
H82 C8 N1 . . . 107.8 ?
H82 C8 C7 . . . 110.1 ?
N1 C8 C7 . . . 113.1(5) ?
H112 C11 H111 . . . 105.8 ?
H112 C11 N1 . . . 112.8 ?
H112 C11 C12 . . . 109.4 ?
H111 C11 N1 . . . 111.2 ?
H111 C11 C12 . . . 107.9 ?
N1 C11 C12 . . . 109.6(3) ?
H121 C12 O12 . . . 114.4 ?
H121 C12 C13 . . . 102.8 ?
H121 C12 C11 . . . 110.5 ?
O12 C12 C13 . . . 112.0(5) ?
O12 C12 C11 . . . 104.6(5) ?
C13 C12 C11 . . . 112.7(3) ?
H131 C13 H132 . . . 106.9 ?
H131 C13 O13 . . . 109.5 ?
H131 C13 C12 . . . 109.9 ?
H132 C13 O13 . . . 110.0 ?
H132 C13 C12 . . . 110.7 ?
O13 C13 C12 . . . 109.8(4) ?
O13 C14 C19 . . . 120.4(5) ?
O13 C14 C15 . . . 119.3(5) ?
C19 C14 C15 . . . 120.2(7) ?
H15 C15 C16 . . . 121.9 ?
H15 C15 C14 . . . 118.7 ?
C16 C15 C14 . . . 119.4(6) ?
H16 C16 C15 . . . 122.0 ?
H16 C16 C17 . . . 117.0 ?
C15 C16 C17 . . . 121.0(6) ?
H17 C17 C16 . . . 123.1 ?
H17 C17 C18 . . . 117.3 ?
C16 C17 C18 . . . 119.6(8) ?
H18 C18 C19 . . . 119.4 ?
H18 C18 C17 . . . 120.3 ?
C19 C18 C17 . . . 120.3(7) ?
H19 C19 C18 . . . 119.9 ?
H19 C19 C14 . . . 120.6 ?
C18 C19 C14 . . . 119.4(5) ?
H211 C21 H212 . . . 109.3 ?
H211 C21 N2 . . . 108.7 ?
H211 C21 C22 . . . 110.2 ?
H212 C21 N2 . . . 107.6 ?
H212 C21 C22 . . . 108.9 ?
N2 C21 C22 . . . 112.2(5) ?
H221 C22 O22 . . . 111.0 ?
H221 C22 C21 . . . 112.2 ?
H221 C22 C23 . . . 106.6 ?
O22 C22 C21 . . . 107.0(4) ?
O22 C22 C23 . . . 111.0(3) ?
C21 C22 C23 . . . 109.0(5) ?
H231 C23 H232 . . . 109.2 ?
H231 C23 O23 . . . 110.2 ?
H231 C23 C22 . . . 112.3 ?
H232 C23 O23 . . . 108.7 ?
H232 C23 C22 . . . 110.7 ?
O23 C23 C22 . . . 105.5(5) ?
O23 C24 C29 . . . 116.1(6) ?
O23 C24 C25 . . . 121.6(5) ?
C29 C24 C25 . . . 122.2(6) ?
H25 C25 C26 . . . 123.0 ?
H25 C25 C24 . . . 119.7 ?
C26 C25 C24 . . . 117.1(7) ?
H26 C26 C27 . . . 119.9 ?
H26 C26 C25 . . . 118.3 ?
C27 C26 C25 . . . 121.8(10) ?
H27 C27 C28 . . . 120.0 ?
H27 C27 C26 . . . 120.6 ?
C28 C27 C26 . . . 119.4(8) ?
H28 C28 C27 . . . 119.9 ?
H28 C28 C29 . . . 118.9 ?
C27 C28 C29 . . . 121.2(7) ?
H29 C29 C24 . . . 120.3 ?
H29 C29 C28 . . . 121.5 ?
C24 C29 C28 . . . 118.2(7) ?
H312 C31 H311 . . . 112.4 ?
H312 C31 N3 . . . 107.1 ?
H312 C31 C32 . . . 109.5 ?
H311 C31 N3 . . . 106.4 ?
H311 C31 C32 . . . 109.3 ?
N3 C31 C32 . . . 112.0(4) ?
H321 C32 O32 . . . 110.9 ?
H321 C32 C31 . . . 111.4 ?
H321 C32 C33 . . . 109.2 ?
O32 C32 C31 . . . 105.3(4) ?
O32 C32 C33 . . . 108.3(4) ?
C31 C32 C33 . . . 111.6(4) ?
H332 C33 H331 . . . 109.6 ?
H332 C33 O33 . . . 112.0 ?
H332 C33 C32 . . . 109.0 ?
H331 C33 O33 . . . 110.6 ?
H331 C33 C32 . . . 107.9 ?
O33 C33 C32 . . . 107.6(4) ?
C35 C34 C39 . . . 120.4(4) ?
C35 C34 O33 . . . 115.0(4) ?
C39 C34 O33 . . . 124.6(5) ?
H35 C35 C34 . . . 118.0 ?
H35 C35 C36 . . . 123.2 ?
C34 C35 C36 . . . 118.8(5) ?
H36 C36 C37 . . . 119.2 ?
H36 C36 C35 . . . 119.4 ?
C37 C36 C35 . . . 121.4(6) ?
H37 C37 C38 . . . 119.3 ?
H37 C37 C36 . . . 122.0 ?
C38 C37 C36 . . . 118.7(5) ?
H38 C38 C37 . . . 121.7 ?
H38 C38 C39 . . . 117.4 ?
C37 C38 C39 . . . 120.9(6) ?
H39 C39 C38 . . . 121.5 ?
H39 C39 C34 . . . 118.7 ?
C38 C39 C34 . . . 119.8(6) ?
H412 C41 H411 . . . 108.1 ?
H412 C41 N4 . . . 109.7 ?
H412 C41 C42 . . . 109.4 ?
H411 C41 N4 . . . 108.8 ?
H411 C41 C42 . . . 108.5 ?
N4 C41 C42 . . . 112.2(5) ?
H421 C42 O42 . . . 109.9 ?
H421 C42 C41 . . . 113.5 ?
H421 C42 C43 . . . 106.1 ?
O42 C42 C41 . . . 105.6(3) ?
O42 C42 C43 . . . 111.1(5) ?
C41 C42 C43 . . . 110.7(5) ?
H432 C43 H431 . . . 108.8 ?
H432 C43 O43 . . . 112.1 ?
H432 C43 C42 . . . 110.3 ?
H431 C43 O43 . . . 110.7 ?
H431 C43 C42 . . . 109.1 ?
O43 C43 C42 . . . 105.8(5) ?
C49 C44 O43 . . . 124.9(5) ?
C49 C44 C45 . . . 119.8(5) ?
O43 C44 C45 . . . 115.3(6) ?
H45 C45 C44 . . . 118.3 ?
H45 C45 C46 . . . 121.9 ?
C44 C45 C46 . . . 119.8(7) ?
H46 C46 C47 . . . 119.7 ?
H46 C46 C45 . . . 119.4 ?
C47 C46 C45 . . . 120.8(5) ?
H47 C47 C46 . . . 121.8 ?
H47 C47 C48 . . . 119.2 ?
C46 C47 C48 . . . 119.0(6) ?
H48 C48 C47 . . . 121.9 ?
H48 C48 C49 . . . 117.5 ?
C47 C48 C49 . . . 120.7(8) ?
H49 C49 C44 . . . 120.2 ?
H49 C49 C48 . . . 119.8 ?
C44 C49 C48 . . . 119.9(6) ?
C11 N1 C8 . . . 108.8(5) ?
C11 N1 C1 . . . 111.0(4) ?
C11 N1 Cd . . . 112.7(3) ?
C8 N1 C1 . . . 109.8(4) ?
C8 N1 Cd . . . 106.7(2) ?
C1 N1 Cd . . . 107.7(3) ?
C3 N2 C21 . . . 110.7(5) ?
C3 N2 C2 . . . 109.9(3) ?
C3 N2 Cd . . . 107.9(3) ?
C21 N2 C2 . . . 109.0(4) ?
C21 N2 Cd . . . 109.3(3) ?
C2 N2 Cd . . . 110.0(4) ?
C5 N3 C4 . . . 110.7(4) ?
C5 N3 C31 . . . 110.1(4) ?
C5 N3 Cd . . . 105.3(4) ?
C4 N3 C31 . . . 110.8(5) ?
C4 N3 Cd . . . 108.0(3) ?
C31 N3 Cd . . . 111.7(3) ?
C6 N4 C41 . . . 108.6(4) ?
C6 N4 C7 . . . 110.3(4) ?
C6 N4 Cd . . . 107.7(4) ?
C41 N4 C7 . . . 110.8(5) ?
C41 N4 Cd . . . 113.6(3) ?
C7 N4 Cd . . . 105.8(3) ?
H121' O12 C12 . . . 111.0 ?
H121' O12 Cd . . . 107.4 ?
C12 O12 Cd . . . 109.3(3) ?
C14 O13 C13 . . . 115.8(4) ?
H221' O22 C22 . . . 109.2 ?
H221' O22 Cd . . . 109.6 ?
C22 O22 Cd . . . 106.6(3) ?
C24 O23 C23 . . . 117.4(5) ?
H321' O32 C32 . . . 107.4 ?
H321' O32 Cd . . . 109.4 ?
C32 O32 Cd . . . 112.5(2) ?
C34 O33 C33 . . . 116.1(4) ?
H421' O42 C42 . . . 103.2 ?
H421' O42 Cd . . . 102.9 ?
C42 O42 Cd . . . 106.8(3) ?
C44 O43 C43 . . . 118.6(5) ?
O1 Cl O4 . . . 110.6(4) ?
O1 Cl O2 . . . 112.0(4) ?
O1 Cl O3 . . . 106.4(6) ?
O4 Cl O2 . . . 109.8(4) ?
O4 Cl O3 . . . 110.5(6) ?
O2 Cl O3 . . . 107.4(5) ?
H51' N5 H52' . . . 108.9 ?
H51' N5 C01 . . . 110.2 ?
H52' N5 C01 . . . 108.7 ?
C06 C01 N5 . . . 118.7(4) ?
C06 C01 C02 . . . 118.5(5) ?
N5 C01 C02 . . . 122.6(6) ?
H02 C02 C03 . . . 118.4 ?
H02 C02 C01 . . . 120.4 ?
C03 C02 C01 . . . 121.2(5) ?
H03 C03 C04 . . . 120.3 ?
H03 C03 C02 . . . 119.7 ?
C04 C03 C02 . . . 120.0(3) ?
C03 C04 C05 . . . 118.9(4) ?
C03 C04 C07 . . . 121.1(3) ?
C05 C04 C07 . . . 120.0(4) ?
H05 C05 C06 . . . 120.3 ?
H05 C05 C04 . . . 118.4 ?
C06 C05 C04 . . . 121.3(5) ?
H06 C06 C05 . . . 120.3 ?
H06 C06 C01 . . . 119.7 ?
C05 C06 C01 . . . 120.0(4) ?
O6 C07 O5 . . . 123.9(4) ?
O6 C07 C04 . . . 116.3(3) ?
O5 C07 C04 . . . 119.8(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cd O32 . . 2.411(3) ?
Cd N4 . . 2.433(5) ?
Cd O12 . . 2.459(4) ?
Cd N1 . . 2.488(4) ?
Cd N2 . . 2.489(5) ?
Cd N3 . . 2.498(5) ?
Cd O22 . . 2.500(4) ?
Cd O42 . . 2.616(4) ?
C1 H11 . . .941 ?
C1 H12 . . .980 ?
C1 N1 . . 1.493(7) ?
C1 C2 . . 1.514(8) ?
C2 H21 . . .958 ?
C2 H22 . . .978 ?
C2 N2 . . 1.490(5) ?
C3 H32 . . .956 ?
C3 H31 . . .957 ?
C3 N2 . . 1.464(7) ?
C3 C4 . . 1.523(5) ?
C4 H41 . . .928 ?
C4 H42 . . .950 ?
C4 N3 . . 1.491(8) ?
C5 H52 . . .921 ?
C5 H51 . . .975 ?
C5 N3 . . 1.469(7) ?
C5 C6 . . 1.534(9) ?
C6 H62 . . .942 ?
C6 H61 . . .945 ?
C6 N4 . . 1.474(7) ?
C7 H71 . . .943 ?
C7 H72 . . .952 ?
C7 N4 . . 1.494(5) ?
C7 C8 . . 1.508(6) ?
C8 H81 . . .963 ?
C8 H82 . . .966 ?
C8 N1 . . 1.485(8) ?
C11 H112 . . .967 ?
C11 H111 . . .979 ?
C11 N1 . . 1.464(7) ?
C11 C12 . . 1.527(7) ?
C12 H121 . . .943 ?
C12 O12 . . 1.425(7) ?
C12 C13 . . 1.508(9) ?
C13 H131 . . .965 ?
C13 H132 . . .966 ?
C13 O13 . . 1.445(6) ?
C14 O13 . . 1.390(9) ?
C14 C19 . . 1.392(9) ?
C14 C15 . . 1.403(7) ?
C15 H15 . . .923 ?
C15 C16 . . 1.379(12) ?
C16 H16 . . .936 ?
C16 C17 . . 1.379(11) ?
C17 H17 . . .951 ?
C17 C18 . . 1.398(8) ?
C18 H18 . . .994 ?
C18 C19 . . 1.388(11) ?
C19 H19 . . .989 ?
C21 H211 . . .923 ?
C21 H212 . . .979 ?
C21 N2 . . 1.480(8) ?
C21 C22 . . 1.496(8) ?
C22 H221 . . .979 ?
C22 O22 . . 1.441(5) ?
C22 C23 . . 1.510(8) ?
C23 H231 . . .922 ?
C23 H232 . . .981 ?
C23 O23 . . 1.424(7) ?
C24 O23 . . 1.359(7) ?
C24 C29 . . 1.385(8) ?
C24 C25 . . 1.411(11) ?
C25 H25 . . .950 ?
C25 C26 . . 1.392(12) ?
C26 H26 . . .941 ?
C26 C27 . . 1.386(13) ?
C27 H27 . . .951 ?
C27 C28 . . 1.379(14) ?
C28 H28 . . .970 ?
C28 C29 . . 1.397(10) ?
C29 H29 . . .970 ?
C31 H312 . . .926 ?
C31 H311 . . .941 ?
C31 N3 . . 1.497(5) ?
C31 C32 . . 1.502(7) ?
C32 H321 . . .960 ?
C32 O32 . . 1.427(8) ?
C32 C33 . . 1.535(5) ?
C33 H332 . . .930 ?
C33 H331 . . .968 ?
C33 O33 . . 1.426(7) ?
C34 C35 . . 1.380(9) ?
C34 C39 . . 1.396(7) ?
C34 O33 . . 1.397(5) ?
C35 H35 . . .980 ?
C35 C36 . . 1.408(7) ?
C36 H36 . . .931 ?
C36 C37 . . 1.387(9) ?
C37 H37 . . .911 ?
C37 C38 . . 1.385(11) ?
C38 H38 . . .953 ?
C38 C39 . . 1.390(7) ?
C39 H39 . . .991 ?
C41 H412 . . .931 ?
C41 H411 . . .985 ?
C41 N4 . . 1.492(8) ?
C41 C42 . . 1.519(6) ?
C42 H421 . . .919 ?
C42 O42 . . 1.430(6) ?
C42 C43 . . 1.531(9) ?
C43 H432 . . .925 ?
C43 H431 . . .982 ?
C43 O43 . . 1.438(6) ?
C44 C49 . . 1.377(11) ?
C44 O43 . . 1.378(6) ?
C44 C45 . . 1.397(7) ?
C45 H45 . . .951 ?
C45 C46 . . 1.400(8) ?
C46 H46 . . .949 ?
C46 C47 . . 1.384(12) ?
C47 H47 . . .958 ?
C47 C48 . . 1.388(9) ?
C48 H48 . . .961 ?
C48 C49 . . 1.409(9) ?
C49 H49 . . .965 ?
O12 H121' . . .853 ?
O22 H221' . . .972 ?
O32 H321' . . .866 ?
O42 H421' . . .789 ?
Cl O1 . . 1.384(7) ?
Cl O4 . . 1.414(6) ?
Cl O2 . . 1.420(7) ?
Cl O3 . . 1.462(13) ?
N5 H51' . . .962 ?
N5 H52' . . 1.018 ?
N5 C01 . . 1.394(7) ?
O5 C07 . . 1.280(5) ?
O6 C07 . . 1.255(6) ?
C01 C06 . . 1.391(8) ?
C01 C02 . . 1.412(6) ?
C02 H02 . . .984 ?
C02 C03 . . 1.393(6) ?
C03 H03 . . .975 ?
C03 C04 . . 1.380(7) ?
C04 C05 . . 1.410(5) ?
C04 C07 . . 1.497(6) ?
C05 H05 . . .927 ?
C05 C06 . . 1.386(6) ?
C06 H06 . . .931 ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
? ? ? ? ? ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O12 H121' O5 . . . 0.85 2.05 2.741(5) 138.1 .
O22 H221' O5 . . . 0.97 1.85 2.788(6) 162.4 .
O32 H321' O6 . . . 0.87 1.75 2.538(5) 149.5 .
O42 H421' O6 . . . 0.79 2.08 2.834(6) 159.4 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?
