# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'A K Powell'
_publ_contact_author_email       POWELL@AOC.UNI-KARLSRUHE.DE

_publ_section_title              
;
One-dimensional Cu(II) Coordination polymers: Tuning
the Structure by Modulating the "Carboxylate Arm" Lengths of
Polycarboxylate Ligands
;
_publ_author_name                'A K Powell'

# Attachment 'ramadan1.CIF'

data_ram65z
_database_code_depnum_ccdc_archive 'CCDC 710321'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H42 Cu3 N2 O23'
_chemical_formula_weight         917.22
_chemical_absolute_configuration ad

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_Hall  'P 2 2ab'

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

_cell_length_a                   22.6828(10)
_cell_length_b                   7.4054(6)
_cell_length_c                   10.1719(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1708.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'pale blue'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             942
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.721
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   
;
XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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  'Stoe Sapphire'
_diffrn_measurement_method       'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8971
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.53
_diffrn_reflns_theta_max         27.35
_reflns_number_total             3673
_reflns_number_gt                3481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CRYSALIS 1.168 (Stoe & Cie GmbH, 2001)'
_computing_cell_refinement       'CRYSALIS 1.168 (Stoe & Cie GmbH, 2001)'
_computing_data_reduction        'CRYSALIS 1.168 (Stoe & Cie GmbH, 2001)'
_computing_structure_solution    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_refinement  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_molecular_graphics    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_publication_material  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0548P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
"Flack H D (1983), Acta Cryst. A39, 876-881, 1435 Friedel pairs'"
_refine_ls_abs_structure_Flack   -0.024(11)
_refine_ls_number_reflns         3673
_refine_ls_number_parameters     270
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0778
_refine_ls_wR_factor_gt          0.0763
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.003
_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 0.034124(12) 0.20640(4) 0.74807(3) 0.01078(9) Uani 1 1 d . . .
Cu2 Cu 0.0000 0.0000 0.33576(4) 0.01363(11) Uani 1 2 d S . .
N1 N 0.12265(9) 0.2596(3) 0.7521(2) 0.0115(4) Uani 1 1 d . . .
C1 C 0.15251(11) 0.0866(4) 0.7922(3) 0.0151(5) Uani 1 1 d . . .
H1A H 0.1353 0.0457 0.8765 0.018 Uiso 1 1 calc R . .
H1B H 0.1948 0.1120 0.8079 0.018 Uiso 1 1 calc R . .
C2 C 0.14778(11) -0.0659(4) 0.6936(3) 0.0150(5) Uani 1 1 d . . .
H2A H 0.1782 -0.1570 0.7157 0.018 Uiso 1 1 calc R . .
H2B H 0.1577 -0.0170 0.6058 0.018 Uiso 1 1 calc R . .
C3 C 0.08864(11) -0.1629(3) 0.6828(3) 0.0133(5) Uani 1 1 d . . .
O1 O 0.04855(7) -0.1193(2) 0.76379(18) 0.0131(4) Uani 1 1 d . . .
O2 O 0.08456(8) -0.2833(3) 0.59778(18) 0.0167(4) Uani 1 1 d . . .
C4 C 0.12732(12) 0.3896(4) 0.8633(3) 0.0160(5) Uani 1 1 d . . .
H4A H 0.1220 0.5140 0.8297 0.019 Uiso 1 1 calc R . .
H4B H 0.1672 0.3812 0.9025 0.019 Uiso 1 1 calc R . .
C5 C 0.08133(12) 0.3523(4) 0.9690(3) 0.0143(5) Uani 1 1 d . . .
O3 O 0.03689(8) 0.2579(3) 0.93614(17) 0.0161(4) Uani 1 1 d . . .
O4 O 0.08993(9) 0.4209(3) 1.07803(19) 0.0219(4) Uani 1 1 d . . .
C6 C 0.15079(11) 0.3381(3) 0.6351(2) 0.0123(5) Uani 1 1 d . . .
C7 C 0.20290(11) 0.4358(4) 0.6515(3) 0.0156(5) Uani 1 1 d . . .
H7A H 0.2208 0.4411 0.7358 0.019 Uiso 1 1 calc R . .
C8 C 0.22897(12) 0.5252(4) 0.5470(3) 0.0196(6) Uani 1 1 d . . .
H8A H 0.2641 0.5923 0.5604 0.023 Uiso 1 1 calc R . .
C9 C 0.20397(12) 0.5169(4) 0.4233(3) 0.0195(5) Uani 1 1 d . . .
H9 H 0.2205 0.5831 0.3523 0.023 Uiso 1 1 calc R . .
C10 C 0.15453(12) 0.4109(4) 0.4043(3) 0.0152(5) Uani 1 1 d . . .
H10 H 0.1385 0.3997 0.3184 0.018 Uiso 1 1 calc R . .
C11 C 0.12755(11) 0.3201(3) 0.5083(3) 0.0121(5) Uani 1 1 d . . .
C12 C 0.07515(11) 0.2056(3) 0.4760(2) 0.0115(5) Uani 1 1 d . . .
O5 O 0.03858(8) 0.1547(2) 0.56137(17) 0.0122(4) Uani 1 1 d . . .
O6 O 0.06931(8) 0.1578(3) 0.35717(18) 0.0158(4) Uani 1 1 d . . .
O7 O 0.0000 0.5000 0.6919(3) 0.0173(5) Uani 1 2 d SD . .
H7 H 0.0215(14) 0.554(5) 0.641(3) 0.026 Uiso 1 1 d D . .
O8 O 0.0000 0.0000 0.1235(3) 0.0367(9) Uani 1 2 d SD . .
H8 H 0.013(2) 0.068(5) 0.078(4) 0.055 Uiso 1 1 d D . .
O9 O 0.05462(9) -0.2087(3) 0.3423(2) 0.0194(4) Uani 1 1 d D . .
H91 H 0.0669(17) -0.229(5) 0.414(3) 0.029 Uiso 1 1 d D . .
H92 H 0.0439(17) -0.284(5) 0.308(4) 0.029 Uiso 1 1 d D . .
O11 O 0.0000 -0.5000 0.2406(3) 0.0165(5) Uani 1 2 d SD . .
H11 H -0.0233(11) -0.449(4) 0.194(3) 0.025 Uiso 1 1 d D . .
O12 O 0.25446(11) -0.2314(4) 0.8967(3) 0.0347(6) Uani 1 1 d D . .
H121 H 0.2810(17) -0.290(6) 0.864(4) 0.052 Uiso 1 1 d D . .
H122 H 0.273(2) -0.129(5) 0.898(5) 0.052 Uiso 1 1 d D . .
O13 O 0.16386(13) 0.0199(4) 0.1831(4) 0.0551(8) Uani 1 1 d D . .
H131 H 0.1314(18) 0.045(8) 0.221(5) 0.083 Uiso 1 1 d D . .
H132 H 0.164(2) -0.094(4) 0.154(6) 0.083 Uiso 1 1 d D . .
O14 O 0.19231(11) 0.6412(4) 1.1120(2) 0.0328(5) Uani 1 1 d D . .
H141 H 0.2106(19) 0.672(7) 1.050(4) 0.049 Uiso 1 1 d D . .
H142 H 0.1596(16) 0.599(6) 1.094(4) 0.049 Uiso 1 1 d D . .


_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 O5 1.9399(18) . ?
Cu1 O3 1.9518(18) . ?
Cu1 O1 1.9897(17) 2 ?
Cu1 N1 2.047(2) . ?
Cu1 O7 2.3776(7) . ?
Cu1 O1 2.4392(17) . ?
Cu2 O6 1.9711(18) . ?
Cu2 O6 1.9711(18) 2 ?
Cu2 O9 1.982(2) . ?
Cu2 O9 1.982(2) 2 ?
Cu2 O8 2.159(3) . ?
N1 C6 1.470(3) . ?
N1 C4 1.490(3) . ?
N1 C1 1.506(3) . ?
C1 C2 1.514(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.525(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.246(3) . ?
C3 O1 1.269(3) . ?
O1 Cu1 1.9896(17) 2 ?
C4 C5 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 O4 1.235(3) . ?
C5 O3 1.272(3) . ?
C6 C7 1.396(4) . ?
C6 C11 1.400(4) . ?
C7 C8 1.385(4) . ?
C7 H7A 0.9500 . ?
C8 C9 1.382(4) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.395(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.496(3) . ?
C12 O5 1.259(3) . ?
C12 O6 1.266(3) . ?
O7 H7 0.82(3) 2_565 ?
O7 Cu1 2.3776(7) 2_565 ?
O7 H7 0.82(3) . ?
O8 H8 0.74(3) 2 ?
O8 H8 0.74(3) . ?
O9 H91 0.80(3) . ?
O9 H92 0.70(3) . ?
O11 H11 0.80(2) 2_545 ?
O11 H11 0.80(2) . ?
O12 H121 0.81(3) . ?
O12 H122 0.87(3) . ?
O13 H131 0.85(3) . ?
O13 H132 0.90(3) . ?
O14 H141 0.79(3) . ?
O14 H142 0.83(3) . ?

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
O5 Cu1 O3 175.17(8) . . ?
O5 Cu1 O1 93.66(8) . 2 ?
O3 Cu1 O1 90.85(8) . 2 ?
O5 Cu1 N1 90.36(8) . . ?
O3 Cu1 N1 84.92(9) . . ?
O1 Cu1 N1 170.25(8) 2 . ?
O5 Cu1 O7 87.83(9) . . ?
O3 Cu1 O7 93.86(9) . . ?
O1 Cu1 O7 90.52(5) 2 . ?
N1 Cu1 O7 98.51(6) . . ?
O5 Cu1 O1 82.07(7) . . ?
O3 Cu1 O1 97.16(7) . . ?
O1 Cu1 O1 78.49(7) 2 . ?
N1 Cu1 O1 93.30(7) . . ?
O7 Cu1 O1 164.50(6) . . ?
O6 Cu2 O6 167.31(11) . 2 ?
O6 Cu2 O9 87.71(8) . . ?
O6 Cu2 O9 91.86(8) 2 . ?
O6 Cu2 O9 91.86(8) . 2 ?
O6 Cu2 O9 87.71(8) 2 2 ?
O9 Cu2 O9 176.15(13) . 2 ?
O6 Cu2 O8 96.34(5) . . ?
O6 Cu2 O8 96.35(5) 2 . ?
O9 Cu2 O8 91.92(6) . . ?
O9 Cu2 O8 91.92(6) 2 . ?
C6 N1 C4 109.19(18) . . ?
C6 N1 C1 111.12(19) . . ?
C4 N1 C1 108.2(2) . . ?
C6 N1 Cu1 119.09(16) . . ?
C4 N1 Cu1 102.08(15) . . ?
C1 N1 Cu1 106.43(15) . . ?
N1 C1 C2 115.0(2) . . ?
N1 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
N1 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2A 107.9 . . ?
C3 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C3 C2 H2B 107.9 . . ?
H2A C2 H2B 107.2 . . ?
O2 C3 O1 125.4(2) . . ?
O2 C3 C2 116.9(2) . . ?
O1 C3 C2 117.6(2) . . ?
C3 O1 Cu1 122.75(17) . 2 ?
C3 O1 Cu1 107.78(15) . . ?
Cu1 O1 Cu1 100.89(7) 2 . ?
N1 C4 C5 111.7(2) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
O4 C5 O3 126.0(2) . . ?
O4 C5 C4 116.8(2) . . ?
O3 C5 C4 117.2(2) . . ?
C5 O3 Cu1 112.99(17) . . ?
C7 C6 C11 118.5(2) . . ?
C7 C6 N1 118.4(2) . . ?
C11 C6 N1 123.0(2) . . ?
C8 C7 C6 121.2(2) . . ?
C8 C7 H7A 119.4 . . ?
C6 C7 H7A 119.4 . . ?
C9 C8 C7 120.2(3) . . ?
C9 C8 H8A 119.9 . . ?
C7 C8 H8A 119.9 . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C9 C10 C11 121.6(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C10 C11 C6 119.2(2) . . ?
C10 C11 C12 117.1(2) . . ?
C6 C11 C12 123.7(2) . . ?
O5 C12 O6 120.4(2) . . ?
O5 C12 C11 122.8(2) . . ?
O6 C12 C11 116.8(2) . . ?
C12 O5 Cu1 130.59(17) . . ?
C12 O6 Cu2 110.77(16) . . ?
H7 O7 Cu1 114(3) 2_565 2_565 ?
H7 O7 Cu1 84(3) 2_565 . ?
Cu1 O7 Cu1 152.18(13) 2_565 . ?
H7 O7 H7 101(5) 2_565 . ?
Cu1 O7 H7 84(3) 2_565 . ?
Cu1 O7 H7 114(3) . . ?
H8 O8 Cu2 128(3) 2 . ?
H8 O8 H8 104(7) 2 . ?
Cu2 O8 H8 128(3) . . ?
Cu2 O9 H91 114(3) . . ?
Cu2 O9 H92 113(3) . . ?
H91 O9 H92 115(5) . . ?
H11 O11 H11 108(4) 2_545 . ?
H121 O12 H122 96(4) . . ?
H131 O13 H132 111(5) . . ?
H141 O14 H142 114(5) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O2 0.82(3) 1.92(3) 2.678(2) 154(3) 1_565
O8 H8 O3 0.74(3) 2.09(3) 2.825(3) 171(5) 1_554
O9 H91 O2 0.80(3) 1.95(3) 2.742(3) 171(4) .
O9 H92 O11 0.70(3) 2.00(3) 2.694(2) 167(4) .
O11 H11 O4 0.80(2) 1.93(2) 2.691(3) 158(3) 2_554
O12 H121 O13 0.81(3) 1.94(4) 2.735(4) 164(5) 3_546
O12 H122 O14 0.87(3) 2.15(3) 3.013(4) 171(5) 3_547
O13 H131 O6 0.85(3) 2.15(4) 2.963(3) 161(5) .
O13 H132 O14 0.90(3) 2.10(3) 2.968(4) 161(5) 1_544
O14 H141 O12 0.79(3) 1.98(3) 2.770(4) 176(5) 1_565
O14 H142 O4 0.83(3) 2.06(3) 2.859(3) 162(5) .

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.742
_refine_diff_density_min         -1.382
_refine_diff_density_rms         0.116

##################################################################

data_ram4
_database_code_depnum_ccdc_archive 'CCDC 710322'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H40 Cu N2 O18'
_chemical_formula_weight         732.14

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   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.3062(13)
_cell_length_b                   7.3389(7)
_cell_length_c                   14.9630(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.636(7)
_cell_angle_gamma                90.00
_cell_volume                     1532.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9482
_cell_measurement_theta_min      1.46
_cell_measurement_theta_max      27.27

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale blue'
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             766
_exptl_absorpt_coefficient_mu    0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.948
_exptl_absorpt_process_details   
;
XPREP in SHELXTL 6.14 (BrukerAXS Inc., 2003)
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Stoe IPDS II'
_diffrn_measurement_method       'area detector'
_diffrn_detector_area_resol_mean 6.667
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9101
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         26.77
_reflns_number_total             3234
_reflns_number_gt                2830
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'WinXpose 1.05 (Stoe & Cie GmbH, 2000)'
_computing_cell_refinement       'X-Area 1.09 (Stoe & Cie GmbH, 2000)'
_computing_data_reduction        'X-Area 1.09 (Stoe & Cie GmbH, 2000)'
_computing_structure_solution    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_structure_refinement  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_molecular_graphics    'SHELXTL 6.14 (BrukerAXS Inc., 2003)'
_computing_publication_material  'SHELXTL 6.14 (BrukerAXS Inc., 2003)'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0902P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3234
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.1103
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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 0.0000 0.0000 0.0000 0.01621(13) Uani 1 2 d S . .
N1 N 0.22030(11) 0.4414(2) -0.11000(10) 0.0167(3) Uani 1 1 d . . .
H1 H 0.1799(18) 0.436(3) -0.0719(17) 0.020 Uiso 1 1 d . . .
C1 C 0.24466(14) 0.2499(2) -0.13353(13) 0.0197(4) Uani 1 1 d . . .
H1A H 0.2953 0.2543 -0.1693 0.024 Uiso 1 1 calc R . .
H1B H 0.1873 0.1925 -0.1723 0.024 Uiso 1 1 calc R . .
C2 C 0.27909(13) 0.1346(3) -0.04851(13) 0.0210(4) Uani 1 1 d . . .
H2A H 0.3287 0.2044 -0.0055 0.025 Uiso 1 1 calc R . .
H2B H 0.3103 0.0243 -0.0665 0.025 Uiso 1 1 calc R . .
C3 C 0.20314(13) 0.0742(2) 0.00287(13) 0.0181(4) Uani 1 1 d . . .
O1 O 0.11645(9) 0.07315(18) -0.04208(9) 0.0190(3) Uani 1 1 d . . .
O2 O 0.23159(10) 0.0220(2) 0.08364(10) 0.0241(3) Uani 1 1 d . . .
O3 O -0.03517(10) 0.7085(2) -0.10227(10) 0.0243(3) Uani 1 1 d . . .
H3 H -0.079(2) 0.640(4) -0.0855(19) 0.037 Uiso 1 1 d . . .
C4 C 0.16840(13) 0.5453(3) -0.19373(12) 0.0184(4) Uani 1 1 d . . .
H4A H 0.1303 0.4596 -0.2384 0.022 Uiso 1 1 calc R . .
H4B H 0.2156 0.6056 -0.2234 0.022 Uiso 1 1 calc R . .
C5 C 0.10277(13) 0.6875(2) -0.16640(13) 0.0187(4) Uani 1 1 d . . .
H5A H 0.1392 0.7614 -0.1151 0.022 Uiso 1 1 calc R . .
H5B H 0.0789 0.7701 -0.2188 0.022 Uiso 1 1 calc R . .
C6 C 0.01916(13) 0.5980(2) -0.13774(12) 0.0166(3) Uani 1 1 d . . .
O4 O 0.00477(10) 0.43493(19) -0.14787(10) 0.0225(3) Uani 1 1 d . . .
O5 O 0.24607(10) 0.5808(2) 0.16788(10) 0.0264(3) Uani 1 1 d . . .
C7 C 0.30376(13) 0.5458(3) -0.05829(12) 0.0174(4) Uani 1 1 d . . .
C8 C 0.37566(13) 0.5945(3) -0.10297(13) 0.0207(4) Uani 1 1 d . . .
H8 H 0.3725 0.5561 -0.1642 0.025 Uiso 1 1 calc R . .
C9 C 0.45216(14) 0.6997(3) -0.05749(14) 0.0225(4) Uani 1 1 d . . .
H9 H 0.5013 0.7339 -0.0878 0.027 Uiso 1 1 calc R . .
C10 C 0.45708(14) 0.7552(3) 0.03222(14) 0.0226(4) Uani 1 1 d . . .
H10 H 0.5088 0.8290 0.0629 0.027 Uiso 1 1 calc R . .
C11 C 0.38593(13) 0.7023(3) 0.07666(13) 0.0201(4) Uani 1 1 d . . .
H11 H 0.3904 0.7383 0.1384 0.024 Uiso 1 1 calc R . .
C12 C 0.30790(13) 0.5972(2) 0.03274(13) 0.0180(4) Uani 1 1 d . . .
C13 C 0.23253(13) 0.5454(3) 0.08565(13) 0.0183(4) Uani 1 1 d . . .
O6 O 0.15771(10) 0.4655(2) 0.03866(10) 0.0225(3) Uani 1 1 d . . .
O7 O -0.07285(10) 0.1284(2) -0.10470(10) 0.0217(3) Uani 1 1 d . . .
H71 H -0.135(2) 0.107(4) -0.1082(19) 0.033 Uiso 1 1 d . . .
H72 H -0.059(2) 0.242(4) -0.1077(19) 0.033 Uiso 1 1 d . . .
O11 O 0.41262(12) 0.4387(2) 0.27847(11) 0.0300(3) Uani 1 1 d . . .
H111 H 0.461(3) 0.499(4) 0.278(2) 0.045 Uiso 1 1 d . . .
H112 H 0.371(3) 0.509(4) 0.245(3) 0.045 Uiso 1 1 d . . .
O12 O 0.40790(11) 0.0978(2) 0.20044(11) 0.0292(3) Uani 1 1 d . . .
H121 H 0.357(3) 0.078(5) 0.163(2) 0.044 Uiso 1 1 d . . .
H122 H 0.405(2) 0.204(5) 0.218(2) 0.044 Uiso 1 1 d . . .


_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 O7 1.9274(14) 3 ?
Cu1 O7 1.9274(14) . ?
Cu1 O1 1.9797(13) . ?
Cu1 O1 1.9797(13) 3 ?
Cu1 O3 2.6144(15) 1_545 ?
Cu1 O3 2.6144(15) 3_565 ?
N1 C7 1.485(2) . ?
N1 C1 1.508(2) . ?
N1 C4 1.515(2) . ?
N1 H1 0.90(3) . ?
C1 C2 1.518(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 O2 1.248(2) . ?
C3 O1 1.275(2) . ?
O3 C6 1.313(2) . ?
O3 Cu1 2.6144(15) 1_565 ?
O3 H3 0.88(3) . ?
C4 C5 1.518(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.507(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 O4 1.218(2) . ?
O5 C13 1.231(2) . ?
C7 C8 1.391(3) . ?
C7 C12 1.402(3) . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.397(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.519(2) . ?
C13 O6 1.286(2) . ?
O7 H71 0.89(3) . ?
O7 H72 0.86(3) . ?
O11 H111 0.82(4) . ?
O11 H112 0.86(4) . ?
O12 H121 0.83(4) . ?
O12 H122 0.83(4) . ?

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
O7 Cu1 O7 180.00(13) 3 . ?
O7 Cu1 O1 92.76(6) 3 . ?
O7 Cu1 O1 87.24(6) . . ?
O7 Cu1 O1 87.24(6) 3 3 ?
O7 Cu1 O1 92.76(6) . 3 ?
O1 Cu1 O1 180.00(7) . 3 ?
O7 Cu1 O3 94.37(6) 3 1_545 ?
O7 Cu1 O3 85.63(6) . 1_545 ?
O1 Cu1 O3 95.93(5) . 1_545 ?
O1 Cu1 O3 84.07(5) 3 1_545 ?
O7 Cu1 O3 85.63(6) 3 3_565 ?
O7 Cu1 O3 94.37(6) . 3_565 ?
O1 Cu1 O3 84.07(5) . 3_565 ?
O1 Cu1 O3 95.93(5) 3 3_565 ?
O3 Cu1 O3 180.00(7) 1_545 3_565 ?
C7 N1 C1 113.67(14) . . ?
C7 N1 C4 111.35(14) . . ?
C1 N1 C4 111.87(14) . . ?
C7 N1 H1 104.3(16) . . ?
C1 N1 H1 108.8(16) . . ?
C4 N1 H1 106.2(16) . . ?
N1 C1 C2 111.91(15) . . ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 . . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 C3 116.60(15) . . ?
C1 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2B 108.1 . . ?
C3 C2 H2B 108.1 . . ?
H2A C2 H2B 107.3 . . ?
O2 C3 O1 125.63(17) . . ?
O2 C3 C2 117.34(16) . . ?
O1 C3 C2 116.94(16) . . ?
C3 O1 Cu1 128.53(12) . . ?
C6 O3 Cu1 133.38(12) . 1_565 ?
C6 O3 H3 106.6(19) . . ?
Cu1 O3 H3 110.9(19) 1_565 . ?
N1 C4 C5 110.07(14) . . ?
N1 C4 H4A 109.6 . . ?
C5 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
C5 C4 H4B 109.6 . . ?
H4A C4 H4B 108.2 . . ?
C6 C5 C4 110.68(15) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
O4 C6 O3 123.92(17) . . ?
O4 C6 C5 121.07(16) . . ?
O3 C6 C5 115.00(16) . . ?
C8 C7 C12 121.29(17) . . ?
C8 C7 N1 118.49(16) . . ?
C12 C7 N1 120.21(16) . . ?
C9 C8 C7 119.57(18) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.26(18) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 119.55(18) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 121.58(17) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C7 117.72(17) . . ?
C11 C12 C13 118.57(16) . . ?
C7 C12 C13 123.71(17) . . ?
O5 C13 O6 124.96(18) . . ?
O5 C13 C12 119.59(17) . . ?
O6 C13 C12 115.46(16) . . ?
Cu1 O7 H71 108.3(18) . . ?
Cu1 O7 H72 115.3(19) . . ?
H71 O7 H72 114(3) . . ?
H111 O11 H112 99(3) . . ?
H121 O12 H122 106(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O6 0.90(3) 1.77(3) 2.579(2) 150(2) .
O3 H3 O6 0.88(3) 1.65(3) 2.518(2) 170(3) 3_565
O7 H71 O2 0.89(3) 1.78(3) 2.606(2) 153(3) 3
O7 H72 O4 0.86(3) 1.85(3) 2.650(2) 153(3) .
O11 H111 O12 0.82(4) 1.97(4) 2.775(2) 165(3) 2_655
O11 H112 O5 0.86(4) 1.98(4) 2.789(2) 157(3) .
O12 H121 O2 0.83(4) 1.96(4) 2.792(2) 174(3) .
O12 H122 O11 0.83(4) 1.94(4) 2.756(2) 169(3) .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.102


