# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_1

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'[Cu (H2 O) (C10 H8 N2) (C15 H10 O4)], 1.5(C2 H3 N)'
_chemical_formula_sum            'C28 H24.5 Cu N3.5 O5'
_chemical_formula_weight         553.55

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   13.7894(11)
_cell_length_b                   17.4839(14)
_cell_length_c                   10.8445(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.4290(10)
_cell_angle_gamma                90
_cell_volume                     2571.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3356
_cell_measurement_theta_min      2.4942
_cell_measurement_theta_max      26.4827

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_F_000             1144
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.894
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.712330
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_diffrn_ambient_temperature      298(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  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15587
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.502
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5863
_reflns_number_gt                3879
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0532P)²+0.3998P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5863
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1104
_refine_ls_wR_factor_gt          0.0964
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.74734(2) 0.24796(2) 0.96023(3) 0.03354(11) Uani 1 1 d . . . . .
O1 O 0.63478(11) 0.31388(9) 0.91460(18) 0.0449(4) Uani 1 1 d . . . . .
O2 O 0.59855(16) 0.32524(15) 1.1041(2) 0.0872(8) Uani 1 1 d . . . . .
O3 O -0.14230(11) 0.31817(8) 0.52030(16) 0.0376(4) Uani 1 1 d . . . . .
O4 O -0.07305(15) 0.32721(14) 0.35168(19) 0.0737(7) Uani 1 1 d . . . . .
O1w O 0.75566(11) 0.25788(9) 1.24861(18) 0.0433(4) Uani 1 1 d . . . . .
H1w1 H 0.7120 0.2851 1.2055 0.065 Uiso 1 1 d R U . . .
H1w2 H 0.8048 0.2855 1.2756 0.065 Uiso 1 1 d R U . . .
N1 N 0.65559(13) 0.15820(10) 0.97415(18) 0.0333(4) Uani 1 1 d . . . . .
N2 N 0.83988(13) 0.34027(10) 0.98126(17) 0.0308(4) Uani 1 1 d . . . . .
C1 C 0.58090(18) 0.33643(15) 0.9909(3) 0.0474(7) Uani 1 1 d . . . . .
C2 C 0.49074(17) 0.37905(14) 0.9327(2) 0.0424(6) Uani 1 1 d . . . . .
C3 C 0.4330(2) 0.4152(2) 1.0050(3) 0.0738(10) Uani 1 1 d . . . . .
H3 H 0.4486 0.4110 1.0918 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3520(2) 0.4579(2) 0.9511(3) 0.0730(10) Uani 1 1 d . . . . .
H4 H 0.3139 0.4817 1.0025 0.088 Uiso 1 1 calc R U . . .
C5 C 0.32663(17) 0.46569(14) 0.8240(3) 0.0453(6) Uani 1 1 d . . . . .
C6 C 0.3839(2) 0.42818(17) 0.7519(3) 0.0576(8) Uani 1 1 d . . . . .
H6 H 0.3674 0.4317 0.6651 0.069 Uiso 1 1 calc R U . . .
C7 C 0.46464(19) 0.38557(16) 0.8042(3) 0.0509(7) Uani 1 1 d . . . . .
H7 H 0.5019 0.3610 0.7527 0.061 Uiso 1 1 calc R U . . .
C8 C 0.24064(16) 0.51436(15) 0.7635(3) 0.0538(8) Uani 1 1 d . . . . .
H8A H 0.2639 0.5526 0.7109 0.065 Uiso 1 1 calc R U . . .
H8B H 0.2138 0.5409 0.8283 0.065 Uiso 1 1 calc R U . . .
C9 C 0.15981(17) 0.46793(14) 0.6849(3) 0.0437(6) Uani 1 1 d . . . . .
C10 C 0.09384(19) 0.42722(16) 0.7401(3) 0.0516(7) Uani 1 1 d . . . . .
H10 H 0.1000 0.4279 0.8269 0.062 Uiso 1 1 calc R U . . .
C11 C 0.01854(18) 0.38528(15) 0.6694(3) 0.0472(6) Uani 1 1 d . . . . .
H11 H -0.0256 0.3589 0.7092 0.057 Uiso 1 1 calc R U . . .
C12 C 0.00829(16) 0.38224(14) 0.5410(2) 0.0385(6) Uani 1 1 d . . . . .
C13 C 0.07508(19) 0.42223(16) 0.4850(3) 0.0542(7) Uani 1 1 d . . . . .
H13 H 0.0702 0.4205 0.3984 0.065 Uiso 1 1 calc R U . . .
C14 C 0.14912(19) 0.46480(17) 0.5563(3) 0.0589(8) Uani 1 1 d . . . . .
H14 H 0.1927 0.4919 0.5166 0.071 Uiso 1 1 calc R U . . .
C15 C -0.07450(17) 0.33955(14) 0.4625(3) 0.0413(6) Uani 1 1 d . . . . .
C16 C 0.57389(18) 0.14636(14) 0.8906(3) 0.0477(7) Uani 1 1 d . . . . .
H16 H 0.5579 0.1806 0.8244 0.057 Uiso 1 1 calc R U . . .
C17 C 0.51159(18) 0.08527(15) 0.8979(3) 0.0489(7) Uani 1 1 d . . . . .
H17 H 0.4554 0.0790 0.8368 0.059 Uiso 1 1 calc R U . . .
C18 C 0.53212(16) 0.03352(12) 0.9950(2) 0.0334(5) Uani 1 1 d . . . . .
C19 C 0.61753(18) 0.04688(14) 1.0816(2) 0.0428(6) Uani 1 1 d . . . . .
H19 H 0.6354 0.0138 1.1490 0.051 Uiso 1 1 calc R U . . .
C20 C 0.67580(17) 0.10883(13) 1.0677(2) 0.0416(6) Uani 1 1 d . . . . .
H20 H 0.7325 0.1165 1.1274 0.050 Uiso 1 1 calc R U . . .
C21 C 0.81831(16) 0.40031(13) 0.9061(2) 0.0378(6) Uani 1 1 d . . . . .
H21 H 0.7597 0.3997 0.8481 0.045 Uiso 1 1 calc R U . . .
C22 C 0.87849(17) 0.46329(13) 0.9099(2) 0.0398(6) Uani 1 1 d . . . . .
H22 H 0.8605 0.5037 0.8548 0.048 Uiso 1 1 calc R U . . .
C23 C 0.96631(15) 0.46651(12) 0.9960(2) 0.0306(5) Uani 1 1 d . . . . .
C24 C 0.98724(17) 0.40413(13) 1.0747(2) 0.0404(6) Uani 1 1 d . . . . .
H24 H 1.0448 0.4034 1.1346 0.048 Uiso 1 1 calc R U . . .
C25 C 0.92346(17) 0.34323(13) 1.0647(2) 0.0382(6) Uani 1 1 d . . . . .
H25 H 0.9394 0.3021 1.1189 0.046 Uiso 1 1 calc R U . . .


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 1.9247(16) . ?
Cu1 O3 1.9282(15) 4_666 ?
Cu1 N1 2.0386(17) . ?
Cu1 N2 2.0444(17) . ?
Cu1 O1w 2.3207(19) 4_565 ?
O1 C1 1.271(3) . ?
O2 C1 1.224(3) . ?
O3 C15 1.272(3) . ?
O3 Cu1 1.9281(15) 4_465 ?
O4 C15 1.225(3) . ?
O1w Cu1 2.3207(19) 4_566 ?
O1w H1w1 0.8401 . ?
O1w H1w2 0.8401 . ?
N1 C20 1.323(3) . ?
N1 C16 1.328(3) . ?
N2 C21 1.330(3) . ?
N2 C25 1.331(3) . ?
C1 C2 1.488(3) . ?
C2 C3 1.369(4) . ?
C2 C7 1.379(4) . ?
C3 C4 1.382(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(4) . ?
C5 C8 1.510(3) . ?
C6 C7 1.374(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.511(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.375(4) . ?
C9 C14 1.376(4) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(3) . ?
C12 C15 1.494(3) . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.386(3) . ?
C18 C18 1.485(4) 3_657 ?
C19 C20 1.373(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.383(3) . ?
C23 C23 1.488(4) 3_767 ?
C24 C25 1.373(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?

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 175.10(8) . 4_666 ?
O1 Cu1 N1 89.86(7) . . ?
O3 Cu1 N1 88.61(7) 4_666 . ?
O1 Cu1 N2 90.80(7) . . ?
O3 Cu1 N2 89.84(7) 4_666 . ?
N1 Cu1 N2 169.33(8) . . ?
O1 Cu1 O1w 87.37(7) . 4_565 ?
O3 Cu1 O1w 97.50(7) 4_666 4_565 ?
N1 Cu1 O1w 100.47(7) . 4_565 ?
N2 Cu1 O1w 90.20(7) . 4_565 ?
C1 O1 Cu1 123.91(17) . . ?
C15 O3 Cu1 127.96(16) . 4_465 ?
Cu1 O1w H1w1 114.6 4_566 . ?
Cu1 O1w H1w2 82.1 4_566 . ?
H1w1 O1w H1w2 108.7 . . ?
C20 N1 C16 117.2(2) . . ?
C20 N1 Cu1 120.78(15) . . ?
C16 N1 Cu1 122.04(16) . . ?
C21 N2 C25 117.15(18) . . ?
C21 N2 Cu1 119.28(14) . . ?
C25 N2 Cu1 123.54(15) . . ?
O2 C1 O1 124.8(2) . . ?
O2 C1 C2 120.3(3) . . ?
O1 C1 C2 114.9(2) . . ?
C3 C2 C7 117.9(2) . . ?
C3 C2 C1 121.0(3) . . ?
C7 C2 C1 121.0(2) . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 121.4(3) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.3(2) . . ?
C4 C5 C8 122.2(3) . . ?
C6 C5 C8 120.5(3) . . ?
C7 C6 C5 122.0(3) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
C5 C8 C9 112.6(2) . . ?
C5 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
C5 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C14 117.6(2) . . ?
C10 C9 C8 120.7(3) . . ?
C14 C9 C8 121.7(3) . . ?
C9 C10 C11 121.5(3) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 H10 119.3 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 118.1(2) . . ?
C11 C12 C15 121.6(2) . . ?
C13 C12 C15 120.3(2) . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
O4 C15 O3 125.1(2) . . ?
O4 C15 C12 120.0(2) . . ?
O3 C15 C12 114.8(2) . . ?
N1 C16 C17 122.7(2) . . ?
N1 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 116.0(2) . . ?
C17 C18 C18 122.1(3) . 3_657 ?
C19 C18 C18 121.9(3) . 3_657 ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
N1 C20 C19 123.5(2) . . ?
N1 C20 H20 118.2 . . ?
C19 C20 H20 118.2 . . ?
N2 C21 C22 123.2(2) . . ?
N2 C21 H21 118.4 . . ?
C22 C21 H21 118.4 . . ?
C21 C22 C23 120.0(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 116.21(19) . . ?
C24 C23 C23 121.8(2) . 3_767 ?
C22 C23 C23 122.0(2) . 3_767 ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
N2 C25 C24 123.2(2) . . ?
N2 C25 H25 118.4 . . ?
C24 C25 H25 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 7.1(4) . . . . ?
Cu1 O1 C1 C2 -172.75(15) . . . . ?
O2 C1 C2 C3 8.8(4) . . . . ?
O1 C1 C2 C3 -171.3(3) . . . . ?
O2 C1 C2 C7 -173.5(3) . . . . ?
O1 C1 C2 C7 6.4(4) . . . . ?
C7 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 176.8(3) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C3 C4 C5 C8 -177.7(3) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
C8 C5 C6 C7 177.7(3) . . . . ?
C5 C6 C7 C2 0.2(5) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C1 C2 C7 C6 -176.9(3) . . . . ?
C4 C5 C8 C9 -115.7(3) . . . . ?
C6 C5 C8 C9 65.4(3) . . . . ?
C5 C8 C9 C10 79.3(3) . . . . ?
C5 C8 C9 C14 -100.9(3) . . . . ?
C14 C9 C10 C11 -0.8(4) . . . . ?
C8 C9 C10 C11 179.1(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C10 C11 C12 C15 -177.8(2) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C15 C12 C13 C14 176.9(2) . . . . ?
C12 C13 C14 C9 1.0(4) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C8 C9 C14 C13 180.0(2) . . . . ?
Cu1 O3 C15 O4 7.5(4) 4_465 . . . ?
Cu1 O3 C15 C12 -171.93(14) 4_465 . . . ?
C11 C12 C15 O4 -168.0(3) . . . . ?
C13 C12 C15 O4 14.2(4) . . . . ?
C11 C12 C15 O3 11.5(3) . . . . ?
C13 C12 C15 O3 -166.3(2) . . . . ?
C20 N1 C16 C17 -0.5(4) . . . . ?
Cu1 N1 C16 C17 179.2(2) . . . . ?
N1 C16 C17 C18 0.5(4) . . . . ?
C16 C17 C18 C19 -0.3(4) . . . . ?
C16 C17 C18 C18 -179.0(3) . . . 3_657 ?
C17 C18 C19 C20 0.2(4) . . . . ?
C18 C18 C19 C20 178.9(3) 3_657 . . . ?
C16 N1 C20 C19 0.4(4) . . . . ?
Cu1 N1 C20 C19 -179.3(2) . . . . ?
C18 C19 C20 N1 -0.3(4) . . . . ?
C25 N2 C21 C22 1.1(4) . . . . ?
Cu1 N2 C21 C22 -177.01(19) . . . . ?
N2 C21 C22 C23 -0.5(4) . . . . ?
C21 C22 C23 C24 -0.3(4) . . . . ?
C21 C22 C23 C23 -179.8(3) . . . 3_767 ?
C22 C23 C24 C25 0.5(4) . . . . ?
C23 C23 C24 C25 -180.0(3) 3_767 . . . ?
C21 N2 C25 C24 -0.8(4) . . . . ?
Cu1 N2 C25 C24 177.17(19) . . . . ?
C23 C24 C25 N2 0.0(4) . . . . ?

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
O1w H1w1 O2 0.84 1.88 2.703(3) 167 .
O1w H1w2 O4 0.84 1.88 2.710(2) 168 1_656

_refine_diff_density_max         0.803
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.053

_shelxl_version_number           2013-2




# start Validation Reply Form
_vrf_CHEMW03_2                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: Four water molecules of the formula unit were SQUEEZEd.
;

#===============================================================================

# SQUEEZE RESULTS
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.500 -0.013 319 120 ' '
2 0.500 1.000 0.013 319 120 ' '
_platon_squeeze_details          
;
 Eight water molecules are presumed to reside in each 
of the two 319 Å³ voids.

 The formula unit was arrived at through a combination of CH&N elemental, 
 infrared and thermogravimetric analyses.  The presence of water was shown by a
 broad band in the 3500-3000 cm⁻¹ range.  In the thermogram, the weight loss 
of 16.1% corresponded to a loss of one coordinated and four lattice water 
molecules (calc. 16.0%).
;
_database_code_depnum_ccdc_archive 'CCDC 1001340'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '[Cu (H2 O) (C10 H8 N2) (C15 H10 O4)], 4H2 O'
_chemical_formula_sum            'C25 H28 Cu N2 O9'
_chemical_formula_weight         564.03

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

loop_
_space_group_symop_operation_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'
'-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                   13.7352(16)
_cell_length_b                   17.888(2)
_cell_length_c                   11.0251(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.460(2)
_cell_angle_gamma                90
_cell_volume                     2663.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1602
_cell_measurement_theta_min      2.4639
_cell_measurement_theta_max      24.7357

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             1172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.873
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5720004
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_diffrn_ambient_temperature      298(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  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7680
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.889
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3041
_reflns_number_gt                1460
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'APEX2 (Bruker, 2011)'
_computing_cell_refinement       'SAINT (Bruker, 2011)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'publCIF (Westrip, 2010)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1065P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3041
_refine_ls_number_parameters     147
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1099
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1942
_refine_ls_wR_factor_gt          0.1698
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49891(18) 0.49882(14) 0.47005(9) 0.0410(5) Uani 0.5 1 d . . P A -1
O1 O 0.61200(19) 0.43428(14) 0.5508(3) 0.0771(10) Uani 1 1 d . . . . .
O2 O 0.6681(3) 0.4248(2) 0.3727(4) 0.1204(15) Uani 1 1 d . . . . .
O1W O 0.5086(15) 0.4919(2) 0.2643(19) 0.046(3) Uani 0.5 1 d . U P A -1
H11 H 0.4518 0.4962 0.2213 0.069 Uiso 0.5 1 d R U P A -1
H12 H 0.5329 0.4505 0.2497 0.069 Uiso 0.5 1 d R U P A -1
C1 C 0.6735(3) 0.4122(2) 0.4842(5) 0.0675(13) Uani 1 1 d . . . . .
C2 C 0.76075(17) 0.36768(14) 0.5542(2) 0.0569(10) Uani 1 1 d G . . . .
C3 C 0.8226(2) 0.32950(18) 0.48877(19) 0.0855(16) Uani 1 1 d G . . . .
H3 H 0.8123 0.3329 0.4032 0.103 Uiso 1 1 calc R U . . .
C4 C 0.8998(2) 0.28622(17) 0.5512(3) 0.0904(17) Uani 1 1 d G . . . .
H4 H 0.9412 0.2607 0.5074 0.108 Uiso 1 1 calc R U . . .
C5 C 0.91517(17) 0.28113(14) 0.6790(3) 0.0669(12) Uani 1 1 d G . . . .
C6 C 0.8533(2) 0.31932(16) 0.7445(2) 0.0764(13) Uani 1 1 d G . . . .
H6 H 0.8636 0.3159 0.8300 0.092 Uiso 1 1 calc R U . . .
C7 C 0.77611(18) 0.36260(15) 0.6821(2) 0.0684(12) Uani 1 1 d G . . . .
H7 H 0.7347 0.3881 0.7259 0.082 Uiso 1 1 calc R U . . .
N1 N 0.4078(2) 0.40958(15) 0.4981(3) 0.0536(8) Uani 1 1 d . . . . .
C8 C 1.0000 0.2319(3) 0.7500 0.088(2) Uani 1 2 d S T P . .
H8A H 1.0259 0.2000 0.6921 0.105 Uiso 0.5 1 calc R U P . .
H8B H 0.9741 0.2000 0.8079 0.105 Uiso 0.5 1 calc R U P . .
C9 C 0.3230(3) 0.4024(2) 0.4173(4) 0.0696(13) Uani 1 1 d . . . . .
H9 H 0.3051 0.4403 0.3599 0.083 Uiso 1 1 calc R U . . .
C10 C 0.2599(3) 0.3411(2) 0.4146(4) 0.0611(12) Uani 1 1 d . . . . .
H10 H 0.2025 0.3387 0.3553 0.073 Uiso 1 1 calc R U . . .
C11 C 0.2822(2) 0.28323(17) 0.5003(3) 0.0425(8) Uani 1 1 d . . . . .
C12 C 0.3705(3) 0.2917(2) 0.5855(3) 0.0512(10) Uani 1 1 d . . . . .
H12A H 0.3895 0.2553 0.6455 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4300(3) 0.3543(2) 0.5807(4) 0.0567(11) Uani 1 1 d . . . . .
H13 H 0.4885 0.3580 0.6381 0.068 Uiso 1 1 calc R U . . .


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 1.918(4) 5_666 ?
Cu1 O1 2.009(3) . ?
Cu1 N1 2.070(4) 5_666 ?
Cu1 N1 2.086(4) . ?
Cu1 O1W 2.30(2) . ?
O1 C1 1.278(5) . ?
O2 C1 1.238(6) . ?
O1W H11 0.8400 . ?
O1W H12 0.8400 . ?
C1 C2 1.527(4) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 C8 1.554(4) . ?
C6 C7 1.3900 . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
N1 C9 1.338(4) . ?
N1 C13 1.341(4) . ?
C8 C5 1.554(4) 6_757 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.394(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.401(4) . ?
C11 C11 1.481(6) 7_556 ?
C12 C13 1.394(5) . ?
C12 H12A 0.9300 . ?
C13 H13 0.9300 . ?

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 O1 160.92(7) 5_666 . ?
O1 Cu1 N1 88.87(15) 5_666 5_666 ?
O1 Cu1 N1 88.56(14) . 5_666 ?
O1 Cu1 N1 90.60(15) 5_666 . ?
O1 Cu1 N1 86.03(14) . . ?
N1 Cu1 N1 161.81(6) 5_666 . ?
O1 Cu1 O1W 95.9(4) 5_666 . ?
O1 Cu1 O1W 103.2(4) . . ?
N1 Cu1 O1W 93.7(3) 5_666 . ?
N1 Cu1 O1W 104.4(3) . . ?
C1 O1 Cu1 117.5(3) . . ?
Cu1 O1W H11 109.7 . . ?
Cu1 O1W H12 109.4 . . ?
H11 O1W H12 109.5 . . ?
O2 C1 O1 125.9(4) . . ?
O2 C1 C2 119.9(4) . . ?
O1 C1 C2 114.2(4) . . ?
C3 C2 C7 120.0 . . ?
C3 C2 C1 119.4(3) . . ?
C7 C2 C1 120.5(3) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 C8 119.35(19) . . ?
C4 C5 C8 120.64(19) . . ?
C5 C6 C7 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C9 N1 C13 116.4(3) . . ?
C9 N1 Cu1 116.6(3) . . ?
C13 N1 Cu1 126.6(2) . . ?
C5 C8 C5 110.9(5) . 6_757 ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8A 109.5 6_757 . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8B 109.5 6_757 . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 123.5(3) . . ?
N1 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
C9 C10 C11 120.6(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C10 C11 C12 115.5(3) . . ?
C10 C11 C11 122.2(3) . 7_556 ?
C12 C11 C11 122.3(4) . 7_556 ?
C13 C12 C11 120.2(3) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
N1 C13 C12 123.8(3) . . ?
N1 C13 H13 118.1 . . ?
C12 C13 H13 118.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 O2 -2.6(6) . . . . ?
Cu1 O1 C1 C2 176.3(2) . . . . ?
O2 C1 C2 C3 -12.5(5) . . . . ?
O1 C1 C2 C3 168.6(3) . . . . ?
O2 C1 C2 C7 170.2(4) . . . . ?
O1 C1 C2 C7 -8.7(4) . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C1 C2 C3 C4 -177.3(3) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C3 C4 C5 C8 178.9(3) . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C8 C5 C6 C7 -178.9(3) . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C1 C2 C7 C6 177.3(3) . . . . ?
C6 C5 C8 C5 -72.7(3) . . . 6_757 ?
C4 C5 C8 C5 108.4(3) . . . 6_757 ?
C13 N1 C9 C10 -1.1(6) . . . . ?
Cu1 N1 C9 C10 172.2(4) . . . . ?
N1 C9 C10 C11 1.2(7) . . . . ?
C9 C10 C11 C12 -0.4(6) . . . . ?
C9 C10 C11 C11 -179.3(4) . . . 7_556 ?
C10 C11 C12 C13 -0.5(6) . . . . ?
C11 C11 C12 C13 178.4(4) 7_556 . . . ?
C9 N1 C13 C12 0.2(6) . . . . ?
Cu1 N1 C13 C12 -172.3(3) . . . . ?
C11 C12 C13 N1 0.6(6) . . . . ?

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
O1w H11 O2 0.84 2.19 2.88(2) 139 6_656
O1w H12 O2 0.84 2.14 2.59(2) 113 .

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-2








_database_code_depnum_ccdc_archive 'CCDC 1001341'
