#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/16/4321632.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_4321632
loop_
_publ_author_name
'Paul S. Donnelly'
'Jack M. Harrowfield'
'Brian W. Skelton'
'Allan H. White'
_publ_contact_author_address
;
   Department of Chemistry
   University of Western Australia
   Nedlands
   Western Australia 6907
   Australia
;
_publ_contact_author_email       bws@crystal.uwa.edu.au
_publ_contact_author_fax         (+61)_08_9380_1118
_publ_contact_author_name        'Skelton, B. W.'
_publ_contact_author_phone       (+61)_08-9380_3481
_publ_section_title
;
 Carboxymethylation of Cage Amines: Control of Alkylation by Metal Ion
 Coordination
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5817
_journal_page_last               5830
_journal_paper_doi               10.1021/ic000346a
_journal_volume                  39
_journal_year                    2000
_chemical_formula_sum            'C18 H44 Cu N12 O18'
_chemical_formula_weight         780.16
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_cell_angle_alpha                90.00000
_cell_angle_beta                 90.00000
_cell_angle_gamma                90.00000
_cell_formula_units_Z            8
_cell_length_a                   43.505(4)
_cell_length_b                   10.4410(10)
_cell_length_c                   13.7110(10)
_cell_measurement_reflns_used    3222
_cell_measurement_temperature    293
_cell_measurement_theta_max      28
_cell_measurement_theta_min      2
_cell_volume                     6228.0(9)
_computing_cell_refinement       'Siemens SAINT (Siemens, 1995)'
_computing_data_collection       'Siemens SMART (Siemens, 1995)'
_computing_data_reduction        xtal
_computing_molecular_graphics    xtal
_computing_publication_material  'xtal BONDLA CIFIO'
_computing_structure_refinement  'xtal CRYLSQ'
_computing_structure_solution    xtal
_diffrn_ambient_temperature      293
_diffrn_measurement_device_type
;
Bruker SMART CCD diffractometer
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_detector       'CCD area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .058
_diffrn_reflns_av_sigmaI/netI    .107
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            3941
_diffrn_reflns_theta_max         29.1
_diffrn_reflns_theta_min         1.87
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    .80
_exptl_absorpt_correction_T_max  .894
_exptl_absorpt_correction_T_min  .642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS; Sheldrick, 1996
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_description       plate
_exptl_crystal_F_000             3272
_exptl_crystal_size_max          .25
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .07
_refine_diff_density_max         .732
_refine_diff_density_min         -.657
_refine_ls_abs_structure_details 'Flack xabs refined'
_refine_ls_abs_structure_Flack   .05(3)
_refine_ls_goodness_of_fit_all   1.553
_refine_ls_goodness_of_fit_ref   1.702
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     302
_refine_ls_number_reflns         1374
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          .085
_refine_ls_R_factor_gt           .05
_refine_ls_shift/su_max          .036
_refine_ls_shift/su_mean         .003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         .055
_refine_ls_wR_factor_ref         .048
_reflns_d_resolution_high        .731
_reflns_d_resolution_low         10.853
_reflns_limit_h_max              57
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                1374
_reflns_number_total             2089
_reflns_threshold_expression     'F    > 4.00 sig(F   )'
_cod_data_source_file            ic000346a_12.cif
_cod_data_source_block           k6g
_cod_original_sg_symbol_Hall     f_2_-2d
_cod_original_formula_sum        'C18 H44 Cu1 N12 O18'
_cod_database_code               4321632
loop_
_symmetry_equiv_pos_as_xyz
+x,+y,+z
-x,-y,+z
1/4-x,1/4+y,1/4+z
3/4+x,3/4-y,1/4+z
+x,1/2+y,1/2+z
1/2+x,+y,1/2+z
1/2+x,1/2+y,+z
-x,1/2-y,1/2+z
1/2-x,-y,1/2+z
1/2-x,1/2-y,+z
1/4-x,3/4+y,3/4+z
3/4-x,1/4+y,3/4+z
3/4-x,3/4+y,1/4+z
3/4+x,1/4-y,3/4+z
1/4+x,3/4-y,3/4+z
1/4+x,1/4-y,1/4+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
Cu .25000 .25000 .75000 .0403(7) Uani ? ? 1.00000 ? ?
N0 .18236(13) .5987(6) .7499(7) .031(3) Uani ? ? 1.00000 ? ?
C1 .20275(14) .4804(5) .7438(6) .029(3) Uani ? ? 1.00000 ? ?
C2a .2090(2) .4515(9) .6375(7) .036(5) Uani ? ? 1.00000 ? ?
N3a .22223(16) .3228(6) .6219(5) .033(4) Uani ? ? 1.00000 ? ?
C4a .2421(2) .3130(8) .5357(6) .034(4) Uani ? ? 1.00000 ? ?
C2b .18584(18) .3703(7) .7935(7) .034(4) Uani ? ? 1.00000 ? ?
N3b .20659(14) .2704(6) .8275(6) .031(4) Uani ? ? 1.00000 ? ?
C4b .19166(17) .1413(7) .8251(7) .031(4) Uani ? ? 1.00000 ? ?
C2c .23204(16) .5214(7) .7988(6) .029(4) Uani ? ? 1.00000 ? ?
N3c .25912(15) .4426(6) .7725(5) .029(4) Uani ? ? 1.00000 ? ?
C4c .28387(18) .4563(7) .8457(7) .031(4) Uani ? ? 1.00000 ? ?
C04 .1498(2) .5856(8) .7173(7) .041(5) Uani ? ? 1.00000 ? ?
C05 .13197(18) .7099(7) .7286(6) .042(5) Uani ? ? 1.00000 ? ?
O51 .10431(13) .7089(6) .7264(6) .065(4) Uani ? ? 1.00000 ? ?
O52 .14898(12) .8091(5) .7415(7) .064(4) Uani ? ? 1.00000 ? ?
N1 .33568(16) .3715(6) .4987(7) .051(4) Uani ? ? 1.00000 ? ?
O11 .33689(18) .3429(7) .5863(5) .075(5) Uani ? ? 1.00000 ? ?
O12 .31364(15) .3352(7) .4478(5) .065(4) Uani ? ? 1.00000 ? ?
O13 .35719(15) .4320(7) .4584(5) .074(5) Uani ? ? 1.00000 ? ?
N2 .21151(16) .3168(6) 1.0880(6) .044(4) Uani ? ? 1.00000 ? ?
O21 .2233(2) .3964(9) 1.0332(7) .129(8) Uani ? ? 1.00000 ? ?
O22 .19376(18) .2364(7) 1.0526(5) .070(4) Uani ? ? 1.00000 ? ?
O23 .21710(15) .3161(7) 1.1738(5) .060(4) Uani ? ? 1.00000 ? ?
O01 .12867(17) .2771(6) .9719(7) .086(6) Uani ? ? 1.00000 ? ?
H0A .1771(19) .605(8) .810(6) .04(2) Uiso ? ? 1.00000 ? ?
H0B .1888(16) .652(7) .713(5) .015(19) Uiso ? ? 1.00000 ? ?
H2aA .1921(17) .457(6) .602(5) .03(2) Uiso ? ? 1.00000 ? ?
H2aB .218(2) .510(9) .619(7) .05(3) Uiso ? ? 1.00000 ? ?
H3a .2112(18) .277(8) .620(6) .02(2) Uiso ? ? 1.00000 ? ?
H4aA .2295(14) .321(6) .474(5) .012(16) Uiso ? ? 1.00000 ? ?
H4aB .2531(19) .365(7) .547(6) .03(2) Uiso ? ? 1.00000 ? ?
H2bA .1775(15) .399(6) .837(5) .012(18) Uiso ? ? 1.00000 ? ?
H2bB .1685(15) .326(6) .752(6) .030(17) Uiso ? ? 1.00000 ? ?
H3b .211(2) .286(9) .881(7) .03(3) Uiso ? ? 1.00000 ? ?
H4bA .1772(16) .143(6) .867(5) .012(16) Uiso ? ? 1.00000 ? ?
H4bB .1855(12) .126(5) .757(6) .003(13) Uiso ? ? 1.00000 ? ?
H2cA .2346(17) .617(7) .783(5) .04(2) Uiso ? ? 1.00000 ? ?
H2cB .2270(16) .518(7) .863(6) .027(19) Uiso ? ? 1.00000 ? ?
H3c .2633(16) .471(7) .725(6) .003(18) Uiso ? ? 1.00000 ? ?
H4cB .293(2) .531(9) .843(6) .04(3) Uiso ? ? 1.00000 ? ?
H4cA .2749(16) .446(6) .905(6) .022(18) Uiso ? ? 1.00000 ? ?
H04A .139(3) .511(13) .767(11) .13(5) Uiso ? ? 1.00000 ? ?
H04B .1509(18) .565(8) .656(6) .03(2) Uiso ? ? 1.00000 ? ?
H52 .1375(17) .885(4) .722(12) .17(7) Uiso ? ? 1.00000 ? ?
H01A .14707 .28115 .99061 .13600 Uiso ? ? 1.00000 ? ?
H01B .11885 .26447 1.02002 .13600 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
C ? 0 144 .002 .002 'Int Tables Vol IV Tables 2.2B and 2.3.1'
H ? 0 352 0 0 'Int Tables Vol IV Tables 2.2B and 2.3.1'
Cu ? 0 8 .263 1.266 'Int Tables Vol IV Tables 2.2B and 2.3.1'
N ? 0 96 .004 .003 'Int Tables Vol IV Tables 2.2B and 2.3.1'
O ? 0 144 .008 .006 '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
N3a Cu N3b . . . 83.3(3) ?
N3a Cu N3c . . . 83.8(3) ?
N3a Cu N3a . . 10 78.2(2) ?
N3a Cu N3b . . 10 151.0(2) ?
N3a Cu N3c . . 10 109.8(3) ?
N3b Cu N3c . . . 89.9(2) ?
N3b Cu N3a . . 10 151.0(3) ?
N3b Cu N3b . . 10 121.6(3) ?
N3b Cu N3c . . 10 81.7(2) ?
N3c Cu N3a . . 10 109.8(3) ?
N3c Cu N3b . . 10 81.7(2) ?
N3c Cu N3c . . 10 162.8(3) ?
N3a Cu N3b 10 . 10 83.3(3) ?
N3a Cu N3c 10 . 10 83.8(3) ?
N3b Cu N3c 10 . 10 89.9(2) ?
C1 N0 C04 . . . 117.5(6) ?
C1 N0 H0A . . . 106(5) ?
C1 N0 H0B . . . 109(5) ?
C04 N0 H0A . . . 92(5) ?
C04 N0 H0B . . . 102(5) ?
H0A N0 H0B . . . 130(7) ?
N0 C1 C2a . . . 108.6(7) ?
N0 C1 C2b . . . 107.8(6) ?
N0 C1 C2c . . . 103.3(5) ?
C2a C1 C2b . . . 111.5(6) ?
C2a C1 C2c . . . 112.2(6) ?
C2b C1 C2c . . . 113.0(6) ?
C1 C2a N3a . . . 113.0(7) ?
C1 C2a H2aA . . . 112(5) ?
C1 C2a H2aB . . . 105(7) ?
N3a C2a H2aA . . . 107(4) ?
N3a C2a H2aB . . . 118(7) ?
H2aA C2a H2aB . . . 101(9) ?
Cu N3a C2a . . . 113.7(5) ?
Cu N3a C4a . . . 106.7(5) ?
Cu N3a H3a . . . 99(7) ?
C2a N3a C4a . . . 114.1(6) ?
C2a N3a H3a . . . 112(7) ?
C4a N3a H3a . . . 110(7) ?
N3a C4a H4aA . . . 111(4) ?
N3a C4a H4aB . . . 99(6) ?
N3a C4a C4a . . 10 109.5(7) ?
H4aA C4a H4aB . . . 118(7) ?
H4aA C4a C4a . . 10 109(4) ?
H4aB C4a C4a . . 10 110(6) ?
C1 C2b N3b . . . 112.6(6) ?
C1 C2b H2bA . . . 106(5) ?
C1 C2b H2bB . . . 116(4) ?
N3b C2b H2bA . . . 109(5) ?
N3b C2b H2bB . . . 108(4) ?
H2bA C2b H2bB . . . 105(6) ?
Cu N3b C2b . . . 116.8(5) ?
Cu N3b C4b . . . 106.1(5) ?
Cu N3b H3b . . . 106(7) ?
C2b N3b C4b . . . 111.7(6) ?
C2b N3b H3b . . . 107(7) ?
C4b N3b H3b . . . 109(7) ?
N3b C4b H4bA . . . 107(4) ?
N3b C4b H4bB . . . 106(3) ?
N3b C4b C4c . . 10 107.4(6) ?
H4bA C4b H4bB . . . 116(6) ?
H4bA C4b C4c . . 10 114(4) ?
H4bB C4b C4c . . 10 105(3) ?
C1 C2c N3c . . . 112.6(6) ?
C1 C2c H2cA . . . 105(4) ?
C1 C2c H2cB . . . 105(4) ?
N3c C2c H2cA . . . 114(4) ?
N3c C2c H2cB . . . 114(4) ?
H2cA C2c H2cB . . . 106(6) ?
Cu N3c C2c . . . 115.0(5) ?
Cu N3c C4c . . . 109.6(5) ?
Cu N3c H3c . . . 108(6) ?
C2c N3c C4c . . . 111.1(6) ?
C2c N3c H3c . . . 100(5) ?
C4c N3c H3c . . . 112(6) ?
N3c C4c H4cB . . . 112(6) ?
N3c C4c H4cA . . . 107(5) ?
N3c C4c C4b . . 10 108.8(7) ?
H4cB C4c H4cA . . . 110(7) ?
H4cB C4c C4b . . 10 106(6) ?
H4cA C4c C4b . . 10 113(4) ?
N0 C04 C05 . . . 112.1(7) ?
N0 C04 H04A . . . 106(7) ?
N0 C04 H04B . . . 105(5) ?
C05 C04 H04A . . . 108(7) ?
C05 C04 H04B . . . 109(5) ?
H04A C04 H04B . . . 116(9) ?
C04 C05 O51 . . . 120.0(7) ?
C04 C05 O52 . . . 114.1(7) ?
O51 C05 O52 . . . 125.9(7) ?
C05 O52 H52 . . . 109(4) ?
O11 N1 O12 . . . 120.2(8) ?
O11 N1 O13 . . . 121.0(8) ?
O12 N1 O13 . . . 118.7(9) ?
O21 N2 O22 . . . 118.6(8) ?
O21 N2 O23 . . . 121.1(8) ?
O22 N2 O23 . . . 120.3(7) ?
H01A O01 H01B . . . 105.4(11) ?
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
Cu N3a . . 2.263(7) ?
Cu N3b . . 2.177(6) ?
Cu N3c . . 2.073(7) ?
Cu N3a . 10 2.263(7) ?
Cu N3b . 10 2.177(6) ?
Cu N3c . 10 2.073(7) ?
N0 C1 . . 1.522(8) ?
N0 C04 . . 1.490(11) ?
N0 H0A . . .86(8) ?
N0 H0B . . .81(7) ?
C1 C2a . . 1.514(13) ?
C1 C2b . . 1.526(10) ?
C1 C2c . . 1.541(10) ?
C2a N3a . . 1.478(11) ?
C2a H2aA . . .88(7) ?
C2a H2aB . . .77(10) ?
N3a C4a . . 1.467(11) ?
N3a H3a . . .68(8) ?
C4a H4aA . . 1.01(7) ?
C4a H4aB . . .74(8) ?
C4a C4a . 10 1.486(12) ?
C2b N3b . . 1.456(10) ?
C2b H2bA . . .76(7) ?
C2b H2bB . . 1.05(7) ?
N3b C4b . . 1.496(9) ?
N3b H3b . . .77(9) ?
C4b H4bA . . .85(7) ?
C4b H4bB . . .98(8) ?
C4b C4c . 10 1.501(11) ?
C2c N3c . . 1.482(10) ?
C2c H2cA . . 1.02(7) ?
C2c H2cB . . .91(8) ?
N3c C4c . . 1.479(11) ?
N3c H3c . . .74(8) ?
C4c H4cB . . .87(9) ?
C4c H4cA . . .91(8) ?
C04 C05 . . 1.521(11) ?
C04 H04A . . 1.13(14) ?
C04 H04B . . .87(8) ?
C05 O51 . . 1.204(10) ?
C05 O52 . . 1.285(10) ?
O52 H52 . . .98(7) ?
N1 O11 . . 1.238(12) ?
N1 O12 . . 1.245(10) ?
N1 O13 . . 1.257(10) ?
N2 O21 . . 1.232(12) ?
N2 O22 . . 1.240(10) ?
N2 O23 . . 1.202(11) ?
O01 H01A . . .842(8) ?
O01 H01B . . .797(9) ?
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
? ? ? ? ? ? ? ? ? ? ?
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
? ? ? ? ? ? ? ? ? ?
