Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global

_journal_coden_Cambridge         1350

_publ_requested_journal          CrystEngComm

loop_
_publ_author_name
S.Batten
'Joshua Strachan-Hatton'
'David Turner'

_publ_contact_author_name        'Dr Stuart Batten '
_publ_contact_author_address     
;
School of Chemistry
Monash University
Clayton
Vic
3800
AUSTRALIA
;

_publ_contact_author_email       STUART.BATTEN@SCI.MONASH.EDU.AU

_publ_section_title              
;
Steric Control of 4-Connected Network Topology in
Hydrogen Bonded Coordination Polymers
;

# Attachment 'DT132F.CIF'

data_dt132f
_database_code_depnum_ccdc_archive 'CCDC 656474'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[Cu(O2CCCCO2)(3,5-Me2Py)(MeOH)].MeOH
;
_chemical_name_common            '[Cu(O2CCCCO2)(3,5-Me2Py)(MeOH)].MeOH'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H26 Cu1 N2 O6'
_chemical_formula_sum            'C20 H26 Cu1 N2 O6'
_chemical_formula_weight         453.97

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   Cc

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

_cell_length_a                   10.5816(8)
_cell_length_b                   14.0388(10)
_cell_length_c                   14.5487(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.380(5)
_cell_angle_gamma                90.00
_cell_volume                     2154.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    5604
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             948
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.8499
_exptl_absorpt_correction_T_max  0.9207
_exptl_absorpt_process_details   SORTAV

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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  'Nonius KappaCCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5604
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_sigmaI/netI    0.0864
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3318
_reflns_number_gt                2575
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Hooft, 1999)'
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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.
Refined as a racemic TWIN.
;

_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^)+(0.2000P)^2^+0.0000P] 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_extinction_expression ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(0)
_refine_ls_number_reflns         3318
_refine_ls_number_parameters     268
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0747
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1130
_refine_ls_wR_factor_gt          0.1027
_refine_ls_goodness_of_fit_ref   1.017
_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 -0.05060(6) 0.23017(4) 0.61173(5) 0.01956(19) Uani 1 1 d . . .
O1 O 0.0611(4) 0.2152(3) 0.5115(3) 0.0220(12) Uani 1 1 d . . .
N1 N -0.1692(5) 0.1324(4) 0.5494(4) 0.0225(13) Uani 1 1 d . . .
C1 C 0.0256(5) 0.2593(4) 0.4377(4) 0.0221(13) Uani 1 1 d . . .
O2 O -0.0648(4) 0.3120(3) 0.4240(3) 0.0324(10) Uani 1 1 d . . .
N2 N 0.0420(5) 0.3494(3) 0.6553(3) 0.0197(10) Uani 1 1 d . . .
C2 C 0.1094(5) 0.2402(4) 0.3620(4) 0.0208(13) Uani 1 1 d . . .
O3 O 0.3501(5) 0.2690(3) 0.2215(3) 0.0235(12) Uani 1 1 d . . .
C3 C 0.1742(5) 0.2302(4) 0.2993(4) 0.0195(12) Uani 1 1 d . . .
O4 O 0.2012(4) 0.1772(3) 0.1513(3) 0.0316(10) Uani 1 1 d . . .
C4 C 0.2477(6) 0.2231(4) 0.2174(4) 0.0210(13) Uani 1 1 d . . .
O5 O 0.0920(5) 0.1335(3) 0.6881(3) 0.0272(11) Uani 1 1 d D . .
C5 C -0.1303(6) 0.0411(4) 0.5439(4) 0.0230(13) Uani 1 1 d . . .
H5 H -0.0494 0.0249 0.5724 0.028 Uiso 1 1 calc R . .
O6 O 0.1845(4) -0.0012(2) 0.5838(3) 0.0356(11) Uani 1 1 d D . .
C6 C -0.2007(6) -0.0299(4) 0.4997(4) 0.0254(14) Uani 1 1 d . . .
C7 C -0.3191(6) -0.0047(4) 0.4600(4) 0.0246(13) Uani 1 1 d . . .
H7 H -0.3720 -0.0522 0.4308 0.030 Uiso 1 1 calc R . .
C8 C -0.3619(6) 0.0890(4) 0.4621(4) 0.0246(14) Uani 1 1 d . . .
C9 C -0.2817(6) 0.1551(4) 0.5085(4) 0.0240(13) Uani 1 1 d . . .
H9 H -0.3090 0.2195 0.5109 0.029 Uiso 1 1 calc R . .
C10 C -0.1521(6) -0.1301(4) 0.4950(4) 0.0303(14) Uani 1 1 d . . .
H10A H -0.1415 -0.1469 0.4307 0.045 Uiso 1 1 calc R . .
H10B H -0.2128 -0.1739 0.5203 0.045 Uiso 1 1 calc R . .
H10C H -0.0702 -0.1350 0.5310 0.045 Uiso 1 1 calc R . .
C11 C -0.4902(6) 0.1182(5) 0.4183(4) 0.0379(16) Uani 1 1 d . . .
H11A H -0.5424 0.1425 0.4659 0.057 Uiso 1 1 calc R . .
H11B H -0.5319 0.0629 0.3881 0.057 Uiso 1 1 calc R . .
H11C H -0.4794 0.1681 0.3725 0.057 Uiso 1 1 calc R . .
C12 C 0.1639(6) 0.3459(4) 0.6908(4) 0.0250(14) Uani 1 1 d . . .
H12 H 0.2063 0.2863 0.6928 0.030 Uiso 1 1 calc R . .
C13 C 0.2293(6) 0.4254(4) 0.7243(4) 0.0247(14) Uani 1 1 d . . .
C14 C 0.1657(6) 0.5118(5) 0.7200(4) 0.0251(16) Uani 1 1 d . . .
H14 H 0.2083 0.5676 0.7425 0.030 Uiso 1 1 calc R . .
C15 C 0.0406(5) 0.5182(4) 0.6832(3) 0.0215(13) Uani 1 1 d . . .
C16 C -0.0160(5) 0.4340(4) 0.6519(4) 0.0207(13) Uani 1 1 d . . .
H16 H -0.1013 0.4365 0.6264 0.025 Uiso 1 1 calc R . .
C17 C 0.3653(6) 0.4169(5) 0.7653(4) 0.0365(16) Uani 1 1 d . . .
H17A H 0.4058 0.4797 0.7659 0.055 Uiso 1 1 calc R . .
H17B H 0.4120 0.3730 0.7279 0.055 Uiso 1 1 calc R . .
H17C H 0.3659 0.3926 0.8285 0.055 Uiso 1 1 calc R . .
C18 C -0.0315(6) 0.6105(4) 0.6777(4) 0.0304(14) Uani 1 1 d . . .
H18A H -0.1160 0.5998 0.6470 0.046 Uiso 1 1 calc R . .
H18B H 0.0142 0.6570 0.6425 0.046 Uiso 1 1 calc R . .
H18C H -0.0397 0.6350 0.7401 0.046 Uiso 1 1 calc R . .
C19 C 0.1225(6) 0.1118(4) 0.7814(4) 0.0346(15) Uani 1 1 d . . .
H19A H 0.2007 0.1450 0.8031 0.052 Uiso 1 1 calc R . .
H19B H 0.1348 0.0429 0.7885 0.052 Uiso 1 1 calc R . .
H19C H 0.0533 0.1323 0.8179 0.052 Uiso 1 1 calc R . .
C20 C 0.1901(7) -0.0038(6) 0.4863(5) 0.043(2) Uani 1 1 d . . .
H20A H 0.1866 0.0613 0.4619 0.065 Uiso 1 1 calc R . .
H20B H 0.1181 -0.0405 0.4586 0.065 Uiso 1 1 calc R . .
H20C H 0.2694 -0.0341 0.4714 0.065 Uiso 1 1 calc R . .
H6O H 0.1939 -0.0510 0.6130 0.044 Uiso 1 1 d D . .
H5O H 0.0927 0.0901 0.6505 0.122 Uiso 1 1 d D . .

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 0.0210(3) 0.0229(3) 0.0157(3) -0.0038(4) 0.0082(2) -0.0037(5)
O1 0.022(3) 0.031(3) 0.014(2) -0.002(2) 0.010(2) -0.0017(19)
N1 0.024(3) 0.029(3) 0.016(3) 0.005(2) 0.013(2) -0.002(2)
C1 0.020(3) 0.026(3) 0.022(3) -0.004(3) 0.004(3) -0.007(3)
O2 0.031(3) 0.036(2) 0.031(2) 0.006(2) 0.009(2) 0.012(2)
N2 0.023(3) 0.021(2) 0.016(2) -0.002(2) 0.008(2) -0.003(2)
C2 0.021(3) 0.027(3) 0.014(3) 0.004(2) 0.001(2) 0.004(3)
O3 0.021(3) 0.032(3) 0.019(3) 0.006(2) 0.013(2) 0.005(2)
C3 0.027(3) 0.017(3) 0.014(3) 0.001(2) 0.002(2) 0.000(3)
O4 0.046(3) 0.032(2) 0.018(2) -0.0014(18) 0.011(2) 0.005(2)
C4 0.030(4) 0.020(3) 0.014(3) 0.002(3) 0.006(3) 0.008(3)
O5 0.039(3) 0.026(2) 0.016(2) 0.005(2) 0.000(2) 0.001(2)
C5 0.021(3) 0.030(3) 0.019(3) 0.001(3) 0.007(3) -0.004(3)
O6 0.044(3) 0.035(2) 0.027(2) -0.0048(18) -0.003(2) 0.010(2)
C6 0.030(4) 0.028(3) 0.020(3) 0.000(3) 0.012(3) -0.003(3)
C7 0.025(3) 0.034(3) 0.017(3) -0.008(2) 0.011(3) -0.009(3)
C8 0.028(3) 0.033(3) 0.013(3) -0.003(3) 0.003(3) -0.007(3)
C9 0.026(4) 0.026(3) 0.022(3) 0.002(3) 0.013(3) 0.000(3)
C10 0.029(3) 0.027(3) 0.036(4) -0.004(3) 0.006(3) -0.006(3)
C11 0.035(4) 0.044(4) 0.034(4) -0.007(3) -0.001(3) -0.002(3)
C12 0.029(4) 0.020(3) 0.027(3) 0.005(3) 0.011(3) 0.004(3)
C13 0.023(3) 0.032(4) 0.019(3) 0.000(3) 0.002(3) -0.004(3)
C14 0.025(4) 0.033(4) 0.018(3) -0.007(3) 0.005(3) -0.014(3)
C15 0.023(3) 0.029(3) 0.012(3) -0.001(2) 0.005(3) -0.001(3)
C16 0.016(3) 0.029(3) 0.018(3) -0.004(2) 0.007(2) -0.006(3)
C17 0.021(3) 0.044(4) 0.044(4) -0.006(3) -0.003(3) -0.002(3)
C18 0.027(3) 0.026(3) 0.039(4) -0.003(3) 0.003(3) 0.004(3)
C19 0.039(4) 0.040(4) 0.023(3) 0.007(3) -0.005(3) -0.004(3)
C20 0.039(5) 0.059(5) 0.034(4) -0.005(4) 0.005(4) 0.017(4)

_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 O1 1.958(5) . ?
Cu1 O3 1.978(5) 4_455 ?
Cu1 N2 2.018(4) . ?
Cu1 N1 2.027(6) . ?
Cu1 O5 2.258(5) . ?
O1 C1 1.271(7) . ?
N1 C9 1.329(8) . ?
N1 C5 1.350(8) . ?
C1 O2 1.214(7) . ?
C1 C2 1.490(8) . ?
N2 C16 1.335(7) . ?
N2 C12 1.353(7) . ?
C2 C3 1.191(7) . ?
O3 C4 1.258(8) . ?
O3 Cu1 1.978(5) 4_554 ?
C3 C4 1.476(7) . ?
O4 C4 1.229(6) . ?
O5 C19 1.405(7) . ?
O5 H5O 0.8190 . ?
C5 C6 1.373(8) . ?
C5 H5 0.9500 . ?
O6 C20 1.425(8) . ?
O6 H6O 0.8201 . ?
C6 C7 1.384(8) . ?
C6 C10 1.502(8) . ?
C7 C8 1.392(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.397(8) . ?
C8 C11 1.511(8) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.382(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(9) . ?
C13 C17 1.521(8) . ?
C14 C15 1.393(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.387(8) . ?
C15 C18 1.502(8) . ?
C16 H16 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O1 Cu1 O3 172.2(2) . 4_455 ?
O1 Cu1 N2 90.94(19) . . ?
O3 Cu1 N2 90.95(19) 4_455 . ?
O1 Cu1 N1 89.0(2) . . ?
O3 Cu1 N1 91.0(2) 4_455 . ?
N2 Cu1 N1 166.4(2) . . ?
O1 Cu1 O5 83.30(17) . . ?
O3 Cu1 O5 89.00(19) 4_455 . ?
N2 Cu1 O5 93.10(17) . . ?
N1 Cu1 O5 100.40(16) . . ?
C1 O1 Cu1 114.9(4) . . ?
C9 N1 C5 117.9(6) . . ?
C9 N1 Cu1 122.7(5) . . ?
C5 N1 Cu1 119.2(4) . . ?
O2 C1 O1 127.9(6) . . ?
O2 C1 C2 119.6(5) . . ?
O1 C1 C2 112.5(5) . . ?
C16 N2 C12 117.9(5) . . ?
C16 N2 Cu1 121.0(4) . . ?
C12 N2 Cu1 121.0(4) . . ?
C3 C2 C1 176.1(6) . . ?
C4 O3 Cu1 118.2(4) . 4_554 ?
C2 C3 C4 175.4(6) . . ?
O4 C4 O3 126.8(6) . . ?
O4 C4 C3 117.6(5) . . ?
O3 C4 C3 115.6(5) . . ?
C19 O5 Cu1 134.5(4) . . ?
C19 O5 H5O 118.2 . . ?
Cu1 O5 H5O 99.0 . . ?
N1 C5 C6 124.0(6) . . ?
N1 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C20 O6 H6O 118.8 . . ?
C5 C6 C7 116.8(5) . . ?
C5 C6 C10 121.7(6) . . ?
C7 C6 C10 121.5(5) . . ?
C6 C7 C8 121.2(5) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C7 C8 C9 116.9(6) . . ?
C7 C8 C11 122.1(5) . . ?
C9 C8 C11 121.0(6) . . ?
N1 C9 C8 123.1(6) . . ?
N1 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C12 C13 122.8(5) . . ?
N2 C12 H12 118.6 . . ?
C13 C12 H12 118.6 . . ?
C12 C13 C14 117.5(6) . . ?
C12 C13 C17 120.6(6) . . ?
C14 C13 C17 121.9(6) . . ?
C13 C14 C15 121.2(6) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 116.4(5) . . ?
C16 C15 C18 120.9(5) . . ?
C14 C15 C18 122.7(5) . . ?
N2 C16 C15 124.1(5) . . ?
N2 C16 H16 118.0 . . ?
C15 C16 H16 118.0 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
O5 H5O O6 0.82 1.92 2.657(5) 150.0 .
O6 H6O O4 0.82 1.86 2.659(5) 165.7 2

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.957
_refine_diff_density_min         -0.715
_refine_diff_density_rms         0.105

# Attachment 'JS24B.CIF'

data_JS24B
_database_code_depnum_ccdc_archive 'CCDC 656475'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
[acetylenedicarboxylato-methanol-bis-pyridine-copper(II)]
;
_chemical_name_common            '[Cu(O2CCCCO2)(py)2(MeOH)'
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cu1 N2 O5'
_chemical_formula_sum            'C15 H14 Cu1 N2 O5'
_chemical_formula_weight         365.82

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   P21/c

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                   7.8631(2)
_cell_length_b                   14.2780(3)
_cell_length_c                   14.3028(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.829(1)
_cell_angle_gamma                90.00
_cell_volume                     1552.28(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(1)
_cell_measurement_reflns_used    17504
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      27.50

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_absorpt_coefficient_mu    1.433
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7176
_exptl_absorpt_correction_T_max  0.7549
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(1)
_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  'Bruker X8 Apex II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17504
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0297
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         27.50
_reflns_number_total             3438
_reflns_number_gt                2904
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART (Bruker)'
_computing_cell_refinement       'Bruker SMART (Bruker)'
_computing_data_reduction        'Bruker SAINT (Bruker)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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.
;

_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^)+(0.2000P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_extinction_expression ?
_refine_ls_number_reflns         3438
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0741
_refine_ls_wR_factor_gt          0.0707
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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 0.43442(3) 0.255188(16) 0.123478(17) 0.01532(8) Uani 1 1 d . . .
O1 O 0.62840(18) 0.27684(10) 0.23923(10) 0.0207(3) Uani 1 1 d . . .
N1 N 0.3334(2) 0.38342(12) 0.12503(12) 0.0173(4) Uani 1 1 d . . .
C1 C 0.7664(3) 0.30671(13) 0.22084(15) 0.0186(4) Uani 1 1 d . . .
H1O H 0.316(4) 0.1877(19) 0.270(2) 0.030(8) Uiso 1 1 d . . .
O2 O 0.78314(19) 0.34065(11) 0.14439(11) 0.0275(4) Uani 1 1 d . . .
N2 N 0.5740(2) 0.14957(11) 0.08690(12) 0.0178(4) Uani 1 1 d . . .
C2 C 0.9278(3) 0.29393(14) 0.30067(15) 0.0187(4) Uani 1 1 d . . .
O3 O 1.22717(18) 0.28122(10) 0.51924(10) 0.0185(3) Uani 1 1 d . . .
C3 C 1.0596(3) 0.27752(14) 0.36108(15) 0.0183(4) Uani 1 1 d . . .
O4 O 1.33154(19) 0.20320(11) 0.41115(11) 0.0254(3) Uani 1 1 d . . .
C4 C 1.2214(3) 0.25048(13) 0.43610(15) 0.0161(4) Uani 1 1 d . . .
O5 O 0.3040(2) 0.17378(11) 0.22095(12) 0.0243(4) Uani 1 1 d . . .
C5 C 0.1668(3) 0.39553(15) 0.13100(15) 0.0218(4) Uani 1 1 d . . .
H5 H 0.1008 0.3425 0.1410 0.026 Uiso 1 1 calc R . .
C6 C 0.0892(3) 0.48271(17) 0.12299(17) 0.0285(5) Uani 1 1 d . . .
H6 H -0.0278 0.4896 0.1288 0.034 Uiso 1 1 calc R . .
C7 C 0.1830(3) 0.56006(16) 0.10646(18) 0.0320(6) Uani 1 1 d . . .
H7 H 0.1311 0.6206 0.1003 0.038 Uiso 1 1 calc R . .
C8 C 0.3530(3) 0.54795(15) 0.09909(17) 0.0285(5) Uani 1 1 d . . .
H8 H 0.4201 0.5999 0.0871 0.034 Uiso 1 1 calc R . .
C9 C 0.4242(3) 0.45884(15) 0.10950(16) 0.0229(5) Uani 1 1 d . . .
H9 H 0.5420 0.4507 0.1055 0.027 Uiso 1 1 calc R . .
C10 C 0.5966(3) 0.06945(15) 0.13683(16) 0.0238(5) Uani 1 1 d . . .
H10 H 0.5429 0.0627 0.1889 0.029 Uiso 1 1 calc R . .
C11 C 0.6947(3) -0.00381(15) 0.11584(17) 0.0274(5) Uani 1 1 d . . .
H11 H 0.7076 -0.0600 0.1525 0.033 Uiso 1 1 calc R . .
C12 C 0.7738(3) 0.00572(15) 0.04095(16) 0.0244(5) Uani 1 1 d . . .
H12 H 0.8424 -0.0438 0.0252 0.029 Uiso 1 1 calc R . .
C13 C 0.7519(3) 0.08836(15) -0.01088(17) 0.0260(5) Uani 1 1 d . . .
H13 H 0.8055 0.0968 -0.0628 0.031 Uiso 1 1 calc R . .
C14 C 0.6512(3) 0.15833(15) 0.01383(16) 0.0225(5) Uani 1 1 d . . .
H14 H 0.6357 0.2150 -0.0222 0.027 Uiso 1 1 calc R . .
C15 C 0.1583(3) 0.11185(18) 0.19550(18) 0.0335(6) Uani 1 1 d . . .
H15A H 0.1207 0.1054 0.1250 0.050 Uiso 1 1 calc R . .
H15B H 0.0611 0.1370 0.2192 0.050 Uiso 1 1 calc R . .
H15C H 0.1925 0.0504 0.2248 0.050 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 0.01172(13) 0.01860(13) 0.01374(14) -0.00197(9) -0.00023(9) 0.00062(9)
O1 0.0157(7) 0.0286(8) 0.0153(7) -0.0018(6) -0.0005(6) 0.0009(6)
N1 0.0143(8) 0.0217(9) 0.0149(9) -0.0010(7) 0.0020(7) -0.0001(7)
C1 0.0191(11) 0.0166(10) 0.0170(11) -0.0026(8) -0.0006(8) -0.0020(8)
O2 0.0203(8) 0.0365(9) 0.0239(9) 0.0066(7) 0.0024(7) -0.0024(7)
N2 0.0137(8) 0.0205(9) 0.0168(9) -0.0022(7) -0.0003(7) -0.0005(6)
C2 0.0169(10) 0.0184(10) 0.0212(11) -0.0007(8) 0.0054(9) -0.0018(8)
O3 0.0164(7) 0.0226(7) 0.0150(7) 0.0003(6) 0.0013(6) 0.0009(6)
C3 0.0177(11) 0.0187(10) 0.0180(11) -0.0018(8) 0.0038(9) -0.0003(8)
O4 0.0200(8) 0.0351(9) 0.0192(8) -0.0017(6) 0.0014(6) 0.0067(7)
C4 0.0158(10) 0.0169(9) 0.0156(10) -0.0016(8) 0.0038(8) -0.0064(8)
O5 0.0256(9) 0.0329(9) 0.0148(8) -0.0039(7) 0.0058(7) -0.0100(7)
C5 0.0197(11) 0.0251(11) 0.0201(11) -0.0032(8) 0.0043(9) -0.0010(8)
C6 0.0201(11) 0.0349(13) 0.0303(13) -0.0053(10) 0.0058(10) 0.0065(9)
C7 0.0326(14) 0.0221(11) 0.0374(14) -0.0038(10) 0.0020(11) 0.0059(9)
C8 0.0295(13) 0.0212(11) 0.0332(13) -0.0022(9) 0.0050(11) -0.0054(9)
C9 0.0186(11) 0.0250(11) 0.0235(12) -0.0007(8) 0.0027(9) -0.0026(8)
C10 0.0250(12) 0.0273(11) 0.0189(11) 0.0034(8) 0.0053(9) 0.0035(9)
C11 0.0321(13) 0.0217(11) 0.0265(13) 0.0038(9) 0.0039(10) 0.0053(9)
C12 0.0185(11) 0.0225(11) 0.0307(13) -0.0063(9) 0.0036(10) 0.0027(8)
C13 0.0265(12) 0.0272(11) 0.0277(12) -0.0007(9) 0.0128(10) 0.0006(9)
C14 0.0216(11) 0.0213(10) 0.0252(12) 0.0021(8) 0.0072(9) 0.0005(8)
C15 0.0368(14) 0.0376(13) 0.0290(13) -0.0089(10) 0.0138(11) -0.0176(11)

_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 O1 1.9673(14) . ?
Cu1 O3 1.9761(14) 4_465 ?
Cu1 N1 1.9982(17) . ?
Cu1 N2 2.0117(17) . ?
Cu1 O5 2.2536(16) . ?
O1 C1 1.255(3) . ?
N1 C9 1.342(3) . ?
N1 C5 1.345(3) . ?
C1 O2 1.233(3) . ?
C1 C2 1.485(3) . ?
N2 C10 1.336(3) . ?
N2 C14 1.342(3) . ?
C2 C3 1.191(3) . ?
O3 C4 1.257(2) . ?
O3 Cu1 1.9761(14) 4_666 ?
C3 C4 1.490(3) . ?
O4 C4 1.221(2) . ?
O5 C15 1.419(3) . ?
O5 H1O 0.71(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.381(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.376(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O1 Cu1 O3 171.22(6) . 4_465 ?
O1 Cu1 N1 94.10(6) . . ?
O3 Cu1 N1 89.77(6) 4_465 . ?
O1 Cu1 N2 88.82(6) . . ?
O3 Cu1 N2 90.35(6) 4_465 . ?
N1 Cu1 N2 159.19(7) . . ?
O1 Cu1 O5 86.45(6) . . ?
O3 Cu1 O5 85.01(6) 4_465 . ?
N1 Cu1 O5 102.74(7) . . ?
N2 Cu1 O5 98.01(7) . . ?
C1 O1 Cu1 113.76(13) . . ?
C9 N1 C5 118.39(18) . . ?
C9 N1 Cu1 120.23(14) . . ?
C5 N1 Cu1 120.99(14) . . ?
O2 C1 O1 127.83(19) . . ?
O2 C1 C2 117.77(18) . . ?
O1 C1 C2 114.31(18) . . ?
C10 N2 C14 118.12(18) . . ?
C10 N2 Cu1 120.63(15) . . ?
C14 N2 Cu1 121.22(14) . . ?
C3 C2 C1 174.9(2) . . ?
C4 O3 Cu1 116.42(13) . 4_666 ?
C2 C3 C4 176.3(2) . . ?
O4 C4 O3 127.77(19) . . ?
O4 C4 C3 118.12(18) . . ?
O3 C4 C3 114.11(18) . . ?
C15 O5 Cu1 128.91(14) . . ?
C15 O5 H1O 109(2) . . ?
Cu1 O5 H1O 120(2) . . ?
N1 C5 C6 121.9(2) . . ?
N1 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C7 119.5(2) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C8 C7 C6 118.9(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
N1 C9 C8 122.6(2) . . ?
N1 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
N2 C10 C11 122.6(2) . . ?
N2 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 118.9(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 118.9(2) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N2 C14 C13 122.5(2) . . ?
N2 C14 H14 118.8 . . ?
C13 C14 H14 118.8 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
O5 H1O O4 0.71(3) 2.00(3) 2.706(2) 169(3) 1_455

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.065