# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                'Jing-Yun Wu'
_publ_contact_author_name        'Wu, Jing-Yun'
_publ_contact_author_email       jyunwu@ncnu.edu.tw

data_cpd2
_database_code_depnum_ccdc_archive 'CCDC 839408'
#TrackingRef '- SI_cpd2.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 Cu N10 O5'
_chemical_formula_weight         574.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.262(3)
_cell_length_b                   13.046(3)
_cell_length_c                   13.058(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.54(3)
_cell_angle_gamma                90.00
_cell_volume                     2537.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3875
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.41

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1188
_exptl_absorpt_coefficient_mu    0.915
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19536
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0744
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         25.05
_reflns_number_total             8693
_reflns_number_gt                6108
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.

Solving the structure of of 2 was re-done in the centrosymmetric space group P21/c. A
disordered model for the H2Cam molecule is properly determined. In the model,
structure was refined in mixed isotropic/anisotropic approximation: isotropic for the
disordered carbon atoms and anisotropic for the rest non-hydrogen atoms. The
H2Cam ligand was disordered over two occupied sites with refined SOF of 0.775 and
0.225. Structure refinement showed that the disorder model for the H2Cam molecule
has had more than disorder of the a-methyl group at the C1 and C3 atoms.
Refinement of the occupancies of the a-methyl group at C1/C3 gave values of
0.449/0.326 and 0.122/0.103 in the major- and minor-occupied parts, respectively, of
the disordered model with reasonable equivalent isotropic displacement parameters.
As a result, the ratio of D-/L-configuration or L-/D-configuration of the H2Cam
ligand is 0.552:0.448 in the final refinement. However, refinement (goodness-of-fit on
F2 = 1.118, final R1 = 0.0479 and wR2 = 0.0958 [I > 2s(I)], and R1 = 0.0664 and
wR2 = 0.1052 (all data)) does not lead to a more reasonable result significantly over
than those (goodness-of-fit on F2 = 1.039, final R1 = 0.0456 and wR2 = 0.0932 [I >
2s(I)], and R1 = 0.0739 and wR2 = 0.1120 (all data)) in space group P21. Further,
refinement in the chiral space group P21 assigns a reasonable absolute structure
parameter (the Flack parameter = 0.02(3)) properly, suggesting a well-solved
D configured structure of the H2Cam ligand. Therefore, solving the structure of 2 in the
chiral space group P21 is preferred over than in the centrosymmetric space group
P21/c on the basis of the refinement results.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+1.5465P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         8693
_refine_ls_number_parameters     710
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.25159(6) 0.35937(5) 0.00713(7) 0.0150(3) Uani 1 1 d . . .
Cu2 Cu 0.25040(7) 0.73783(5) 0.50383(7) 0.0140(3) Uani 1 1 d . . .
O1 O 0.2766(5) 0.3543(6) 0.6584(4) 0.0395(18) Uani 1 1 d . . .
O2 O 0.1664(5) 0.2390(6) 0.6352(4) 0.0414(17) Uani 1 1 d . . .
H2 H 0.1670 0.2491 0.6973 0.062 Uiso 1 1 calc R . .
O3 O 0.2597(4) 0.2853(5) 0.1750(4) 0.0214(15) Uani 1 1 d . A .
O4 O 0.1344(7) 0.2022(8) 0.1872(8) 0.030(2) Uiso 0.57 1 d P A 1
H4 H 0.1212 0.2099 0.1233 0.045 Uiso 1 1 calc R . .
O4' O 0.1662(7) 0.1599(7) 0.1835(7) 0.026(2) Uiso 0.43 1 d P A 2
O5 O 0.2563(3) 0.4583(5) 0.8443(4) 0.0233(16) Uani 1 1 d . . .
H101 H 0.2761 0.4277 0.7934 0.035 Uiso 1 1 d R . .
H102 H 0.3062 0.4814 0.8825 0.035 Uiso 1 1 d R . .
O6 O 0.2572(4) 0.8171(5) 0.6692(4) 0.0240(16) Uani 1 1 d . . .
O7 O 0.1262(4) 0.8746(6) 0.6872(4) 0.0455(19) Uani 1 1 d . . .
H7 H 0.1131 0.8632 0.6239 0.068 Uiso 1 1 calc R . .
O8 O 0.2739(4) 0.7454(5) 1.1547(4) 0.0344(17) Uani 1 1 d . . .
O9 O 0.1715(5) 0.8682(8) 1.1405(5) 0.070(3) Uani 1 1 d . . .
H9 H 0.1605 0.8400 1.1924 0.105 Uiso 1 1 calc R . .
O10 O 0.2570(3) 0.6435(4) 0.3439(3) 0.0190(15) Uani 1 1 d . . .
H103 H 0.3052 0.6086 0.3638 0.029 Uiso 1 1 d R . .
H104 H 0.2675 0.6621 0.2846 0.029 Uiso 1 1 d R . .
N1 N 0.1027(5) 0.2124(5) -0.0188(5) 0.0182(18) Uani 1 1 d . . .
N2 N 0.1524(4) 0.2668(5) -0.0698(5) 0.0184(17) Uani 1 1 d . . .
N3 N 0.1208(5) 0.2547(6) -0.1722(4) 0.0218(18) Uani 1 1 d . . .
N4 N 0.0511(4) 0.1928(6) -0.1887(5) 0.0208(18) Uani 1 1 d . . .
N5 N -0.1566(4) -0.0429(5) -0.0322(4) 0.0124(16) Uani 1 1 d . . .
N6 N 0.3939(5) 0.5106(5) 0.0162(5) 0.0160(18) Uani 1 1 d . . .
N7 N 0.3504(4) 0.4533(5) 0.0752(5) 0.0168(17) Uani 1 1 d . . .
N8 N 0.3856(4) 0.4656(6) 0.1753(5) 0.0227(19) Uani 1 1 d . . .
N9 N 0.4533(5) 0.5319(6) 0.1857(5) 0.027(2) Uani 1 1 d . . .
N10 N 0.6541(4) 0.7595(6) 0.0174(5) 0.0171(17) Uani 1 1 d . . .
N11 N 0.0969(5) 0.8795(6) 0.4797(5) 0.0183(18) Uani 1 1 d . . .
N12 N 0.1481(4) 0.8274(5) 0.4257(4) 0.0145(16) Uani 1 1 d . . .
N13 N 0.1199(4) 0.8432(6) 0.3252(5) 0.0200(18) Uani 1 1 d . . .
N14 N 0.0494(4) 0.9082(5) 0.3101(5) 0.0194(18) Uani 1 1 d . . .
N15 N -0.1583(4) 1.1353(5) 0.4689(5) 0.0178(17) Uani 1 1 d . . .
N16 N 0.3936(5) 0.5886(6) 0.5163(5) 0.021(2) Uani 1 1 d . . .
N17 N 0.3498(4) 0.6451(5) 0.5729(5) 0.0157(17) Uani 1 1 d . . .
N18 N 0.3872(5) 0.6355(6) 0.6753(5) 0.0255(19) Uani 1 1 d . . .
N19 N 0.4568(5) 0.5718(6) 0.6848(5) 0.0231(19) Uani 1 1 d . . .
N20 N 0.6566(4) 0.3402(6) 0.5200(4) 0.0150(17) Uani 1 1 d . . .
C1 C 0.2662(6) 0.2245(8) 0.5216(6) 0.022(2) Uani 1 1 d . . .
C2 C 0.2037(7) 0.2472(9) 0.4137(6) 0.037(2) Uani 1 1 d . . .
C3 C 0.2577(6) 0.2034(7) 0.3404(5) 0.024(2) Uani 1 1 d . A .
H3 H 0.2576 0.1285 0.3465 0.029 Uiso 1 1 calc R . .
C4 C 0.3522(6) 0.2413(11) 0.3810(6) 0.050(3) Uani 1 1 d . . .
H4A H 0.3625 0.3046 0.3466 0.061 Uiso 1 1 calc R . .
H4B H 0.3956 0.1906 0.3696 0.061 Uiso 1 1 calc R . .
C5 C 0.3589(7) 0.2590(10) 0.5007(7) 0.063(4) Uani 1 1 d . . .
H5A H 0.3699 0.3307 0.5184 0.076 Uiso 1 1 calc R . .
H5B H 0.4072 0.2184 0.5420 0.076 Uiso 1 1 calc R . .
C6 C 0.2378(7) 0.2800(8) 0.6118(6) 0.029(3) Uani 1 1 d . . .
C7 C 0.2226(6) 0.2320(7) 0.2249(6) 0.025(2) Uani 1 1 d . . .
C8 C 0.2720(6) 0.1100(5) 0.5489(6) 0.062(3) Uani 1 1 d . . .
H8A H 0.2176 0.0887 0.5682 0.093 Uiso 1 1 calc R . .
H8B H 0.3220 0.0982 0.6065 0.093 Uiso 1 1 calc R . .
H8C H 0.2801 0.0713 0.4891 0.093 Uiso 1 1 calc R . .
C9 C 0.1128(6) 0.1910(10) 0.4014(7) 0.071(4) Uani 1 1 d . . .
H9A H 0.0736 0.2114 0.3368 0.107 Uiso 1 1 calc R . .
H9B H 0.0859 0.2085 0.4591 0.107 Uiso 1 1 calc R . .
H9C H 0.1224 0.1183 0.4009 0.107 Uiso 1 1 calc R . .
C10 C 0.1892(8) 0.3607(8) 0.3976(7) 0.075(4) Uani 1 1 d . . .
H10A H 0.2445 0.3926 0.3914 0.113 Uiso 1 1 calc R . .
H10B H 0.1695 0.3893 0.4565 0.113 Uiso 1 1 calc R . .
H10C H 0.1444 0.3725 0.3348 0.113 Uiso 1 1 calc R . .
C11 C 0.0407(5) 0.1669(6) -0.0921(6) 0.0111(18) Uani 1 1 d . . .
C12 C -0.1660(5) 0.0023(6) -0.1254(6) 0.019(2) Uani 1 1 d . . .
H12 H -0.2171 -0.0119 -0.1768 0.022 Uiso 1 1 calc R . .
C13 C -0.1030(5) 0.0698(6) -0.1495(6) 0.017(2) Uani 1 1 d . . .
H13 H -0.1106 0.0975 -0.2165 0.021 Uiso 1 1 calc R . .
C14 C -0.0273(5) 0.0956(6) -0.0710(6) 0.017(2) Uani 1 1 d . . .
C15 C -0.0202(6) 0.0493(7) 0.0276(6) 0.021(2) Uani 1 1 d . . .
H15 H 0.0282 0.0642 0.0824 0.025 Uiso 1 1 calc R . .
C16 C -0.0842(6) -0.0169(7) 0.0419(7) 0.023(2) Uani 1 1 d . . .
H16 H -0.0779 -0.0468 0.1078 0.027 Uiso 1 1 calc R . .
C17 C 0.4562(6) 0.5569(7) 0.0846(6) 0.020(2) Uani 1 1 d . . .
C18 C 0.6473(6) 0.7377(8) 0.1161(6) 0.028(2) Uani 1 1 d . . .
H18 H 0.6904 0.7644 0.1712 0.033 Uiso 1 1 calc R . .
C19 C 0.5810(6) 0.6791(7) 0.1394(6) 0.033(2) Uani 1 1 d . . .
H19 H 0.5744 0.6741 0.2084 0.039 Uiso 1 1 calc R . .
C20 C 0.5239(5) 0.6273(7) 0.0612(5) 0.016(2) Uani 1 1 d . . .
C21 C 0.5293(6) 0.6484(7) -0.0397(6) 0.026(2) Uani 1 1 d . . .
H21 H 0.4895 0.6180 -0.0955 0.032 Uiso 1 1 calc R . .
C22 C 0.5951(6) 0.7159(7) -0.0583(7) 0.028(3) Uani 1 1 d . . .
H22 H 0.5972 0.7308 -0.1274 0.034 Uiso 1 1 calc R . .
C23 C 0.2512(6) 0.8891(7) 0.8344(6) 0.027(2) Uani 1 1 d . . .
H25' H 0.3164 0.8912 0.8407 0.041 Uiso 0.40 1 calc PR B 2
C25 C 0.2657(7) 0.8703(9) 1.0193(6) 0.034(3) Uani 1 1 d . . .
H25 H 0.2646 0.9447 1.0296 0.051 Uiso 0.60 1 calc PR C 1
C28 C 0.2129(6) 0.8568(8) 0.7232(6) 0.026(2) Uani 1 1 d . D .
C29 C 0.2405(7) 0.8190(9) 1.1109(7) 0.038(3) Uani 1 1 d . D .
C24 C 0.1957(9) 0.8420(11) 0.9133(9) 0.018(3) Uani 0.65 1 d P D 1
C26 C 0.3537(9) 0.8417(11) 0.9980(9) 0.027(3) Uiso 0.65 1 d P D 1
H26A H 0.3679 0.7711 1.0182 0.032 Uiso 0.65 1 calc PR D 1
H26B H 0.4005 0.8854 1.0374 0.032 Uiso 0.65 1 calc PR D 1
C27 C 0.3466(8) 0.8557(12) 0.8775(8) 0.024(3) Uiso 0.65 1 d P D 1
H27A H 0.3886 0.9075 0.8644 0.029 Uiso 0.65 1 calc PR D 1
H27B H 0.3593 0.7918 0.8456 0.029 Uiso 0.65 1 calc PR D 1
C30 C 0.2386(9) 1.0061(8) 0.8293(8) 0.053(4) Uani 0.65 1 d P D 1
H30A H 0.2607 1.0349 0.8977 0.080 Uiso 0.65 1 calc PR D 1
H30B H 0.1760 1.0219 0.8062 0.080 Uiso 0.65 1 calc PR D 1
H30C H 0.2713 1.0345 0.7809 0.080 Uiso 0.65 1 calc PR D 1
C31 C 0.1006(9) 0.8865(15) 0.9096(11) 0.059(5) Uani 0.65 1 d P D 1
H31A H 0.0736 0.8509 0.9593 0.089 Uiso 0.65 1 calc PR D 1
H31B H 0.0640 0.8780 0.8404 0.089 Uiso 0.65 1 calc PR D 1
H31C H 0.1054 0.9581 0.9269 0.089 Uiso 0.65 1 calc PR D 1
C32 C 0.1819(7) 0.7271(8) 0.8994(8) 0.022(3) Uiso 0.65 1 d P D 1
H32A H 0.1466 0.7026 0.9469 0.033 Uiso 0.65 1 calc PR D 1
H32B H 0.2392 0.6933 0.9140 0.033 Uiso 0.65 1 calc PR D 1
H32C H 0.1513 0.7127 0.8286 0.033 Uiso 0.65 1 calc PR D 1
C24' C 0.2364(14) 0.8140(15) 0.9198(14) 0.025(5) Uiso 0.35 1 d P D 2
C26' C 0.2258(13) 0.9979(15) 0.8730(13) 0.023(5) Uiso 0.35 1 d P D 2
H26C H 0.2652 1.0504 0.8558 0.027 Uiso 0.35 1 calc PR D 2
H26D H 0.1643 1.0154 0.8403 0.027 Uiso 0.35 1 calc PR D 2
C27' C 0.2373(12) 0.9885(15) 0.9923(13) 0.031(5) Uani 0.35 1 d P D 2
H27C H 0.1815 1.0045 1.0131 0.037 Uiso 0.35 1 calc PR D 2
H27D H 0.2836 1.0347 1.0283 0.037 Uiso 0.35 1 calc PR D 2
C30' C 0.3768(16) 0.880(2) 1.0552(19) 0.076(8) Uani 0.35 1 d P D 2
H30D H 0.3995 0.9120 1.0003 0.113 Uiso 0.35 1 calc PR D 2
H30E H 0.4023 0.8122 1.0678 0.113 Uiso 0.35 1 calc PR D 2
H30F H 0.3927 0.9196 1.1182 0.113 Uiso 0.35 1 calc PR D 2
C31' C 0.2784(12) 0.7106(12) 0.9158(12) 0.030(4) Uiso 0.35 1 d P D 2
H31D H 0.2616 0.6665 0.9672 0.045 Uiso 0.35 1 calc PR D 2
H31E H 0.3425 0.7175 0.9304 0.045 Uiso 0.35 1 calc PR D 2
H31F H 0.2580 0.6815 0.8472 0.045 Uiso 0.35 1 calc PR D 2
C32' C 0.1325(13) 0.8050(14) 0.9041(13) 0.026(4) Uiso 0.35 1 d P D 2
H32D H 0.1069 0.8722 0.9038 0.040 Uiso 0.35 1 calc PR D 2
H32E H 0.1183 0.7655 0.9603 0.040 Uiso 0.35 1 calc PR D 2
H32F H 0.1084 0.7716 0.8385 0.040 Uiso 0.35 1 calc PR D 2
C33 C 0.0368(6) 0.9276(7) 0.4052(7) 0.020(2) Uani 1 1 d . . .
C34 C -0.0873(6) 1.1103(7) 0.5453(6) 0.013(2) Uani 1 1 d . . .
H34 H -0.0810 1.1401 0.6112 0.015 Uiso 1 1 calc R . .
C35 C -0.0229(6) 1.0407(6) 0.5277(6) 0.016(2) Uani 1 1 d . . .
H35 H 0.0249 1.0228 0.5821 0.019 Uiso 1 1 calc R . .
C36 C -0.0303(6) 0.9981(7) 0.4289(6) 0.017(2) Uani 1 1 d . . .
C37 C -0.1028(6) 1.0266(6) 0.3520(6) 0.020(2) Uani 1 1 d . . .
H37 H -0.1095 0.9997 0.2848 0.024 Uiso 1 1 calc R . .
C38 C -0.1652(6) 1.0940(6) 0.3731(6) 0.019(2) Uani 1 1 d . . .
H38 H -0.2138 1.1117 0.3197 0.022 Uiso 1 1 calc R . .
C39 C 0.4597(6) 0.5432(7) 0.5887(6) 0.016(2) Uani 1 1 d . . .
C40 C 0.5924(5) 0.3799(7) 0.4405(6) 0.016(2) Uani 1 1 d . . .
H40 H 0.5925 0.3613 0.3718 0.019 Uiso 1 1 calc R . .
C41 C 0.5280(5) 0.4459(7) 0.4586(6) 0.016(2) Uani 1 1 d . . .
H41 H 0.4859 0.4726 0.4025 0.019 Uiso 1 1 calc R . .
C42 C 0.5253(5) 0.4734(7) 0.5612(6) 0.020(2) Uani 1 1 d . . .
C43 C 0.5923(6) 0.4352(7) 0.6415(6) 0.026(2) Uani 1 1 d . . .
H43 H 0.5953 0.4547 0.7107 0.031 Uiso 1 1 calc R . .
C44 C 0.6549(6) 0.3673(8) 0.6167(6) 0.034(3) Uani 1 1 d . . .
H44 H 0.6977 0.3396 0.6713 0.041 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0124(6) 0.0143(6) 0.0182(6) -0.0019(5) 0.0030(5) -0.0002(5)
Cu2 0.0100(6) 0.0132(6) 0.0192(5) 0.0015(4) 0.0039(4) 0.0003(4)
O1 0.059(5) 0.041(4) 0.018(3) -0.007(4) 0.008(3) 0.005(4)
O2 0.057(5) 0.052(4) 0.021(3) -0.015(3) 0.022(3) -0.015(4)
O3 0.020(4) 0.024(4) 0.021(3) 0.004(3) 0.006(3) -0.004(3)
O5 0.021(4) 0.031(4) 0.017(3) -0.004(3) 0.004(3) 0.005(3)
O6 0.025(4) 0.029(4) 0.018(3) -0.005(3) 0.005(3) 0.004(3)
O7 0.032(3) 0.097(5) 0.008(2) 0.006(3) 0.0064(18) 0.035(3)
O8 0.045(4) 0.032(4) 0.025(3) 0.009(3) 0.006(3) 0.014(4)
O9 0.063(5) 0.118(7) 0.037(4) 0.015(5) 0.027(4) 0.043(6)
O10 0.018(4) 0.020(3) 0.017(3) 0.001(3) 0.001(3) 0.006(3)
N1 0.019(4) 0.019(4) 0.019(4) -0.006(3) 0.009(3) -0.005(3)
N2 0.015(4) 0.019(4) 0.019(3) 0.007(3) 0.001(3) 0.001(3)
N3 0.020(4) 0.030(5) 0.014(3) 0.001(4) 0.003(3) -0.005(4)
N4 0.017(4) 0.022(4) 0.021(4) 0.005(3) 0.000(3) -0.009(4)
N5 0.012(4) 0.015(4) 0.010(3) -0.001(3) 0.000(3) 0.005(3)
N6 0.015(4) 0.019(4) 0.016(4) 0.000(3) 0.007(3) -0.008(4)
N7 0.016(4) 0.019(4) 0.013(4) -0.002(3) -0.002(3) 0.003(4)
N8 0.022(4) 0.031(5) 0.015(3) 0.002(3) 0.005(3) -0.015(4)
N9 0.023(5) 0.033(5) 0.021(4) 0.006(3) -0.003(3) -0.009(4)
N10 0.013(4) 0.019(4) 0.019(4) 0.000(3) 0.001(3) 0.000(4)
N11 0.015(4) 0.023(4) 0.016(4) -0.006(3) 0.003(3) 0.002(3)
N12 0.020(4) 0.012(4) 0.013(3) 0.001(3) 0.007(3) -0.001(3)
N13 0.018(4) 0.021(4) 0.021(4) 0.002(4) 0.005(3) 0.006(4)
N14 0.019(4) 0.024(4) 0.015(4) 0.002(3) 0.003(3) 0.007(4)
N15 0.018(4) 0.018(4) 0.019(4) 0.001(3) 0.008(3) 0.000(4)
N16 0.019(5) 0.021(5) 0.021(4) 0.001(4) 0.000(4) -0.001(4)
N17 0.012(4) 0.016(4) 0.022(4) -0.002(3) 0.011(3) 0.007(4)
N18 0.027(5) 0.026(5) 0.020(4) -0.001(3) -0.001(3) 0.004(4)
N19 0.022(5) 0.028(4) 0.019(4) 0.004(3) 0.004(3) 0.016(4)
N20 0.014(4) 0.016(4) 0.015(3) -0.003(3) 0.004(3) -0.001(3)
C1 0.024(5) 0.024(6) 0.019(4) 0.000(4) 0.006(4) 0.006(5)
C2 0.047(6) 0.050(6) 0.016(4) 0.006(5) 0.009(4) 0.008(6)
C3 0.043(6) 0.018(5) 0.016(4) -0.001(3) 0.015(4) 0.000(4)
C4 0.036(5) 0.085(7) 0.028(4) 0.021(4) 0.002(3) 0.015(4)
C5 0.040(5) 0.107(9) 0.040(5) 0.002(5) 0.003(4) 0.005(5)
C6 0.040(7) 0.035(6) 0.010(4) -0.001(4) 0.004(4) 0.003(5)
C7 0.034(5) 0.025(5) 0.016(4) -0.001(4) 0.008(4) -0.012(4)
C8 0.108(8) 0.034(4) 0.050(5) 0.010(4) 0.031(5) 0.015(5)
C9 0.053(7) 0.136(10) 0.025(4) 0.009(6) 0.008(4) -0.051(7)
C10 0.132(10) 0.070(6) 0.027(4) 0.006(4) 0.023(4) 0.072(7)
C11 0.009(4) 0.011(4) 0.013(4) -0.002(3) 0.003(3) -0.003(4)
C12 0.006(5) 0.029(5) 0.019(5) -0.006(4) -0.002(4) 0.001(4)
C13 0.015(5) 0.021(5) 0.017(4) 0.009(4) 0.006(4) 0.002(4)
C14 0.018(5) 0.014(5) 0.018(4) 0.001(4) 0.004(4) 0.008(4)
C15 0.017(5) 0.022(5) 0.020(5) -0.005(4) -0.003(4) -0.001(4)
C16 0.027(6) 0.023(5) 0.018(5) -0.001(4) 0.005(4) -0.004(5)
C17 0.020(5) 0.020(5) 0.020(5) 0.006(4) 0.006(4) 0.008(4)
C18 0.024(5) 0.036(5) 0.020(4) 0.000(4) -0.002(4) -0.009(5)
C19 0.039(5) 0.041(5) 0.018(4) 0.002(4) 0.006(4) -0.017(4)
C20 0.013(5) 0.021(5) 0.011(4) 0.006(4) -0.002(4) 0.001(4)
C21 0.022(6) 0.028(6) 0.026(5) -0.006(4) 0.000(4) -0.013(5)
C22 0.026(6) 0.031(7) 0.028(5) 0.004(5) 0.009(5) -0.003(5)
C23 0.051(7) 0.017(5) 0.016(4) -0.002(4) 0.011(4) 0.003(4)
C25 0.054(7) 0.032(6) 0.017(4) 0.006(5) 0.011(4) 0.004(6)
C28 0.027(5) 0.027(5) 0.024(4) 0.009(4) 0.006(4) 0.006(4)
C29 0.029(7) 0.049(8) 0.036(6) -0.022(5) 0.004(5) -0.005(6)
C24 0.009(6) 0.028(7) 0.019(6) 0.003(6) 0.005(5) 0.009(6)
C30 0.111(11) 0.020(6) 0.031(7) -0.002(5) 0.020(7) -0.011(6)
C31 0.020(7) 0.117(14) 0.041(8) 0.007(9) 0.006(6) 0.017(9)
C27' 0.024(11) 0.038(11) 0.031(10) -0.008(9) 0.008(8) 0.007(9)
C30' 0.067(19) 0.10(2) 0.061(16) -0.005(16) 0.019(14) -0.034(17)
C33 0.014(5) 0.018(5) 0.026(5) 0.000(4) 0.000(4) -0.005(4)
C34 0.014(5) 0.014(5) 0.012(4) 0.002(4) 0.005(4) 0.002(4)
C35 0.018(5) 0.015(4) 0.014(4) 0.001(3) 0.003(4) 0.005(4)
C36 0.018(5) 0.021(5) 0.013(4) -0.001(4) 0.007(4) 0.000(4)
C37 0.024(6) 0.017(5) 0.018(4) 0.000(4) 0.002(4) -0.002(5)
C38 0.030(6) 0.013(5) 0.012(4) -0.004(4) 0.003(4) -0.002(4)
C39 0.013(5) 0.018(5) 0.014(4) 0.003(4) -0.003(4) 0.010(4)
C40 0.011(5) 0.022(6) 0.012(4) 0.005(4) -0.001(4) 0.000(4)
C41 0.010(5) 0.021(5) 0.014(4) 0.001(4) -0.001(3) -0.001(4)
C42 0.017(5) 0.015(5) 0.030(5) 0.004(4) 0.007(4) 0.006(4)
C43 0.024(4) 0.038(5) 0.013(4) -0.002(3) -0.004(3) 0.016(4)
C44 0.032(5) 0.054(7) 0.015(4) 0.002(5) -0.001(4) 0.027(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Cu1 N7 1.996(7) . ?
Cu1 N5 2.010(6) 2 ?
Cu1 N10 2.018(7) 2_645 ?
Cu1 N2 2.024(7) . ?
Cu1 O3 2.375(5) . ?
Cu2 N17 1.996(7) . ?
Cu2 N20 2.023(7) 2_656 ?
Cu2 N15 2.027(7) 2_546 ?
Cu2 N12 2.037(7) . ?
Cu2 O6 2.376(5) . ?
O1 C6 1.226(10) . ?
O2 C6 1.308(11) . ?
O3 C7 1.178(9) . ?
O4 C7 1.384(12) . ?
O4' C7 1.310(12) . ?
O6 C28 1.196(10) . ?
O7 C28 1.324(9) . ?
O8 C29 1.175(11) . ?
O9 C29 1.359(11) . ?
N1 N2 1.321(9) . ?
N1 C11 1.330(9) . ?
N2 N3 1.330(8) . ?
N3 N4 1.316(9) . ?
N4 C11 1.347(9) . ?
N5 C12 1.332(9) . ?
N5 C16 1.345(10) . ?
N5 Cu1 2.010(6) 2_545 ?
N6 C17 1.304(11) . ?
N6 N7 1.347(9) . ?
N7 N8 1.311(8) . ?
N8 N9 1.331(9) . ?
N9 C17 1.369(10) . ?
N10 C22 1.313(10) . ?
N10 C18 1.346(9) . ?
N10 Cu1 2.018(7) 2_655 ?
N11 C33 1.340(10) . ?
N11 N12 1.345(9) . ?
N12 N13 1.306(8) . ?
N13 N14 1.351(9) . ?
N14 C33 1.322(10) . ?
N15 C34 1.344(9) . ?
N15 C38 1.345(9) . ?
N15 Cu2 2.027(7) 2_556 ?
N16 N17 1.324(9) . ?
N16 C39 1.359(10) . ?
N17 N18 1.340(8) . ?
N18 N19 1.333(9) . ?
N19 C39 1.319(10) . ?
N20 C44 1.316(9) . ?
N20 C40 1.366(9) . ?
N20 Cu2 2.023(7) 2_646 ?
C1 C6 1.524(12) . ?
C1 C8 1.534(12) . ?
C1 C2 1.550(10) . ?
C1 C5 1.564(12) . ?
C2 C10 1.504(14) . ?
C2 C3 1.505(12) . ?
C2 C9 1.547(13) . ?
C3 C4 1.508(12) . ?
C3 C7 1.533(10) . ?
C4 C5 1.561(11) . ?
C11 C14 1.464(11) . ?
C12 C13 1.390(11) . ?
C13 C14 1.409(10) . ?
C14 C15 1.404(10) . ?
C15 C16 1.347(12) . ?
C17 C20 1.463(11) . ?
C18 C19 1.355(12) . ?
C19 C20 1.369(10) . ?
C20 C21 1.365(10) . ?
C21 C22 1.396(12) . ?
C23 C28 1.503(10) . ?
C23 C27 1.507(14) . ?
C23 C24' 1.54(2) . ?
C23 C30 1.538(13) . ?
C23 C26' 1.58(2) . ?
C23 C24 1.592(15) . ?
C25 C24' 1.47(2) . ?
C25 C26 1.477(15) . ?
C25 C29 1.492(13) . ?
C25 C24 1.597(14) . ?
C25 C27' 1.62(2) . ?
C25 C30' 1.66(2) . ?
C24 C32 1.520(16) . ?
C24 C31 1.554(18) . ?
C26 C27 1.564(14) . ?
C24' C31' 1.50(2) . ?
C24' C32' 1.56(3) . ?
C26' C27' 1.53(2) . ?
C33 C36 1.459(12) . ?
C34 C35 1.393(11) . ?
C35 C36 1.387(9) . ?
C36 C37 1.375(10) . ?
C37 C38 1.368(11) . ?
C39 C42 1.455(11) . ?
C40 C41 1.365(11) . ?
C41 C42 1.397(10) . ?
C42 C43 1.389(10) . ?
C43 C44 1.392(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N7 Cu1 N5 92.3(3) . 2 ?
N7 Cu1 N10 88.4(3) . 2_645 ?
N5 Cu1 N10 179.1(3) 2 2_645 ?
N7 Cu1 N2 176.8(3) . . ?
N5 Cu1 N2 88.3(3) 2 . ?
N10 Cu1 N2 91.0(3) 2_645 . ?
N7 Cu1 O3 87.5(2) . . ?
N5 Cu1 O3 90.1(2) 2 . ?
N10 Cu1 O3 89.3(2) 2_645 . ?
N2 Cu1 O3 95.6(2) . . ?
N17 Cu2 N20 88.8(3) . 2_656 ?
N17 Cu2 N15 90.5(3) . 2_546 ?
N20 Cu2 N15 178.8(3) 2_656 2_546 ?
N17 Cu2 N12 176.7(3) . . ?
N20 Cu2 N12 91.8(3) 2_656 . ?
N15 Cu2 N12 88.9(3) 2_546 . ?
N17 Cu2 O6 88.5(2) . . ?
N20 Cu2 O6 87.7(2) 2_656 . ?
N15 Cu2 O6 91.3(2) 2_546 . ?
N12 Cu2 O6 94.7(2) . . ?
C7 O3 Cu1 144.7(6) . . ?
C28 O6 Cu2 143.7(6) . . ?
N2 N1 C11 105.9(7) . . ?
N1 N2 N3 108.7(7) . . ?
N1 N2 Cu1 121.4(5) . . ?
N3 N2 Cu1 129.7(6) . . ?
N4 N3 N2 109.9(7) . . ?
N3 N4 C11 104.8(6) . . ?
C12 N5 C16 117.0(7) . . ?
C12 N5 Cu1 119.4(5) . 2_545 ?
C16 N5 Cu1 123.5(6) . 2_545 ?
C17 N6 N7 104.0(7) . . ?
N8 N7 N6 110.9(7) . . ?
N8 N7 Cu1 128.7(6) . . ?
N6 N7 Cu1 120.3(5) . . ?
N7 N8 N9 108.8(6) . . ?
N8 N9 C17 104.1(7) . . ?
C22 N10 C18 116.5(8) . . ?
C22 N10 Cu1 123.8(6) . 2_655 ?
C18 N10 Cu1 119.6(6) . 2_655 ?
C33 N11 N12 103.9(7) . . ?
N13 N12 N11 110.2(6) . . ?
N13 N12 Cu2 130.0(6) . . ?
N11 N12 Cu2 119.8(5) . . ?
N12 N13 N14 108.9(6) . . ?
C33 N14 N13 104.9(6) . . ?
C34 N15 C38 118.7(8) . . ?
C34 N15 Cu2 120.5(6) . 2_556 ?
C38 N15 Cu2 120.7(5) . 2_556 ?
N17 N16 C39 104.0(7) . . ?
N16 N17 N18 110.4(7) . . ?
N16 N17 Cu2 120.7(5) . . ?
N18 N17 Cu2 128.7(6) . . ?
N19 N18 N17 108.0(6) . . ?
C39 N19 N18 106.1(6) . . ?
C44 N20 C40 117.8(8) . . ?
C44 N20 Cu2 119.1(6) . 2_646 ?
C40 N20 Cu2 123.0(5) . 2_646 ?
C6 C1 C8 107.2(7) . . ?
C6 C1 C2 112.9(7) . . ?
C8 C1 C2 113.0(8) . . ?
C6 C1 C5 114.8(9) . . ?
C8 C1 C5 108.2(8) . . ?
C2 C1 C5 100.8(7) . . ?
C10 C2 C3 111.7(9) . . ?
C10 C2 C9 110.5(10) . . ?
C3 C2 C9 110.9(9) . . ?
C10 C2 C1 111.0(8) . . ?
C3 C2 C1 101.1(7) . . ?
C9 C2 C1 111.4(8) . . ?
C2 C3 C4 105.4(7) . . ?
C2 C3 C7 114.2(7) . . ?
C4 C3 C7 111.7(7) . . ?
C3 C4 C5 104.5(8) . . ?
C4 C5 C1 105.5(8) . . ?
O1 C6 O2 123.0(9) . . ?
O1 C6 C1 124.8(10) . . ?
O2 C6 C1 112.1(8) . . ?
O3 C7 O4' 123.1(7) . . ?
O3 C7 O4 121.0(8) . . ?
O4' C7 O4 31.8(6) . . ?
O3 C7 C3 125.5(8) . . ?
O4' C7 C3 106.8(8) . . ?
O4 C7 C3 112.8(8) . . ?
N1 C11 N4 110.7(7) . . ?
N1 C11 C14 124.7(7) . . ?
N4 C11 C14 124.6(7) . . ?
N5 C12 C13 123.0(7) . . ?
C12 C13 C14 119.0(7) . . ?
C15 C14 C13 116.9(8) . . ?
C15 C14 C11 122.0(7) . . ?
C13 C14 C11 121.1(7) . . ?
C16 C15 C14 119.3(8) . . ?
N5 C16 C15 124.7(8) . . ?
N6 C17 N9 112.3(8) . . ?
N6 C17 C20 126.2(8) . . ?
N9 C17 C20 121.6(8) . . ?
N10 C18 C19 123.5(8) . . ?
C18 C19 C20 119.8(8) . . ?
C21 C20 C19 117.3(9) . . ?
C21 C20 C17 121.5(8) . . ?
C19 C20 C17 121.2(7) . . ?
C20 C21 C22 119.4(8) . . ?
N10 C22 C21 123.0(8) . . ?
C28 C23 C27 114.9(8) . . ?
C28 C23 C24' 115.7(10) . . ?
C27 C23 C24' 80.1(10) . . ?
C28 C23 C30 102.6(7) . . ?
C27 C23 C30 113.9(10) . . ?
C24' C23 C30 128.8(10) . . ?
C28 C23 C26' 119.2(9) . . ?
C27 C23 C26' 115.1(11) . . ?
C24' C23 C26' 104.8(11) . . ?
C30 C23 C26' 24.0(7) . . ?
C28 C23 C24 111.5(8) . . ?
C27 C23 C24 104.7(8) . . ?
C24' C23 C24 26.1(8) . . ?
C30 C23 C24 109.4(9) . . ?
C26' C23 C24 86.4(10) . . ?
C24' C25 C26 79.8(11) . . ?
C24' C25 C29 113.7(12) . . ?
C26 C25 C29 116.1(10) . . ?
C24' C25 C24 26.3(8) . . ?
C26 C25 C24 104.0(9) . . ?
C29 C25 C24 110.5(9) . . ?
C24' C25 C27' 105.4(11) . . ?
C26 C25 C27' 114.3(12) . . ?
C29 C25 C27' 119.9(11) . . ?
C24 C25 C27' 86.2(9) . . ?
C24' C25 C30' 112.3(14) . . ?
C26 C25 C30' 32.7(9) . . ?
C29 C25 C30' 103.3(11) . . ?
C24 C25 C30' 135.3(12) . . ?
C27' C25 C30' 101.6(14) . . ?
O6 C28 O7 121.0(7) . . ?
O6 C28 C23 122.7(8) . . ?
O7 C28 C23 116.4(8) . . ?
O8 C29 O9 121.8(10) . . ?
O8 C29 C25 126.7(10) . . ?
O9 C29 C25 111.5(10) . . ?
C32 C24 C31 105.1(13) . . ?
C32 C24 C23 112.5(10) . . ?
C31 C24 C23 117.4(11) . . ?
C32 C24 C25 112.3(10) . . ?
C31 C24 C25 112.6(10) . . ?
C23 C24 C25 97.0(8) . . ?
C25 C26 C27 107.1(10) . . ?
C23 C27 C26 105.0(10) . . ?
C25 C24' C31' 115.4(15) . . ?
C25 C24' C23 104.9(13) . . ?
C31' C24' C23 114.6(15) . . ?
C25 C24' C32' 105.0(15) . . ?
C31' C24' C32' 110.9(16) . . ?
C23 C24' C32' 105.0(14) . . ?
C27' C26' C23 105.7(14) . . ?
C26' C27' C25 105.3(13) . . ?
N14 C33 N11 112.1(8) . . ?
N14 C33 C36 124.9(8) . . ?
N11 C33 C36 122.8(8) . . ?
N15 C34 C35 121.4(8) . . ?
C36 C35 C34 119.7(8) . . ?
C37 C36 C35 117.5(8) . . ?
C37 C36 C33 120.4(8) . . ?
C35 C36 C33 122.1(8) . . ?
C38 C37 C36 120.8(8) . . ?
N15 C38 C37 121.9(8) . . ?
N19 C39 N16 111.5(8) . . ?
N19 C39 C42 125.3(7) . . ?
N16 C39 C42 123.2(8) . . ?
C41 C40 N20 122.2(7) . . ?
C40 C41 C42 120.0(7) . . ?
C43 C42 C41 117.6(8) . . ?
C43 C42 C39 118.2(8) . . ?
C41 C42 C39 124.2(7) . . ?
C42 C43 C44 118.8(8) . . ?
N20 C44 C43 123.5(7) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.081