#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:08:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179558 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/27/4502735.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4502735
loop_
_publ_author_name
'Delgado, Fernando S.'
'Jiménez, Claudio A.'
'Lorenzo-Luis, Pablo'
'Pasán, Jorge'
'Fabelo, Oscar'
'Cañadillas-Delgado, Laura'
'Lloret, Frances'
'Julve, Miguel'
'Ruiz-Pérez, Catalina'
_publ_section_title
;
 Novel Malonate-Containing Coordination Compounds with Ligands Having N-
 and NO-Donors: Synthesis, Structures, and Magnetic Properties
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              599
_journal_paper_doi               10.1021/cg200675u
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C18 H22 Cu2 N2 O12'
_chemical_formula_weight         585.46
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.346(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.3547(3)
_cell_length_b                   22.517(2)
_cell_length_c                   9.1684(11)
_cell_measurement_temperature    293(2)
_cell_volume                     1083.85(17)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7555
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         6.41
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    2.032
_exptl_absorpt_correction_T_max  0.614
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3037
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.1014
_reflns_number_gt                2021
_reflns_number_total             3037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200675u_si_004.cif
_cod_data_source_block           compound3
_cod_original_cell_volume        1083.86(18)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4502735
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_group
Cu1 Cu 0.62064(6) 0.214905(15) 0.39118(3) 0.02044(12) Uani 1 1 d . .
C1 C 0.3817(5) 0.32692(14) 0.4299(3) 0.0269(6) Uani 1 1 d . .
C2 C 0.6493(6) 0.34759(14) 0.4936(4) 0.0281(7) Uani 1 1 d . .
C3 C 0.7995(5) 0.30527(13) 0.6051(3) 0.0225(6) Uani 1 1 d . .
O1 O 0.3464(3) 0.27164(9) 0.3992(2) 0.0317(5) Uani 1 1 d . .
O2 O 0.8154(4) 0.25153(9) 0.5710(2) 0.0272(4) Uani 1 1 d . .
O3 O 0.2070(4) 0.36246(11) 0.4079(3) 0.0525(7) Uani 1 1 d . .
O4 O 0.9062(3) 0.32712(9) 0.7276(2) 0.0260(4) Uani 1 1 d . .
N1 N 0.8482(4) 0.14242(11) 0.4310(3) 0.0259(5) Uani 1 1 d . .
C10 C 1.0013(9) 0.13369(19) 0.5602(5) 0.0689(16) Uani 1 1 d . .
C11 C 1.1873(10) 0.0911(2) 0.5854(7) 0.096(2) Uani 1 1 d . .
C12 C 1.2231(7) 0.05411(17) 0.4720(7) 0.0682(15) Uani 1 1 d . .
C13 C 1.0586(11) 0.0617(2) 0.3401(7) 0.0681(15) Uani 1 1 d . .
C14 C 0.8776(7) 0.10592(16) 0.3224(4) 0.0449(9) Uani 1 1 d . .
C15A C 1.4453(17) 0.0150(4) 0.5487(12) 0.026(4) Uani 0.43(2) 1 d P 1
C15B C 1.4066(17) 0.0052(3) 0.4465(11) 0.037(3) Uani 0.57(2) 1 d P 2
O1W O 0.8530(4) 0.25743(12) 0.2445(2) 0.0407(6) Uani 1 1 d . .
O2W O 0.2364(6) 0.48217(13) 0.4593(4) 0.0779(9) Uani 1 1 d . .
H1 H 0.726(5) 0.3516(14) 0.410(3) 0.024(8) Uiso 1 1 d . .
H2 H 0.634(6) 0.3800(17) 0.545(4) 0.035(9) Uiso 1 1 d . .
H15 H 1.443(9) -0.014(2) 0.364(5) 0.058(12) Uiso 1 1 d . .
H14 H 0.790(7) 0.113(2) 0.230(5) 0.062(13) Uiso 1 1 d . .
H10 H 1.005(7) 0.1583(19) 0.620(4) 0.047(11) Uiso 1 1 d . .
H13 H 1.066(7) 0.041(2) 0.272(4) 0.054(13) Uiso 1 1 d . .
H11 H 1.327(9) 0.086(2) 0.684(5) 0.085(14) Uiso 1 1 d . .
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'
Cu Cu 0.3201 1.2651 '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'
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
O4 Cu1 O2 173.16(9) 4_565 .
O4 Cu1 O1 90.74(8) 4_565 .
O2 Cu1 O1 88.44(8) . .
O4 Cu1 N1 89.43(9) 4_565 .
O2 Cu1 N1 89.18(9) . .
O1 Cu1 N1 161.30(10) . .
O4 Cu1 O1W 93.36(8) 4_565 .
O2 Cu1 O1W 93.41(8) . .
O1 Cu1 O1W 104.77(10) . .
N1 Cu1 O1W 93.89(9) . .
O3 C1 O1 121.8(3) . .
O3 C1 C2 120.1(3) . .
O1 C1 C2 118.2(2) . .
C3 C2 C1 113.9(3) . .
O4 C3 O2 123.9(3) . .
O4 C3 C2 116.5(3) . .
O2 C3 C2 119.5(2) . .
C1 O1 Cu1 124.20(17) . .
C3 O2 Cu1 124.44(17) . .
C3 O4 Cu1 126.48(19) . 4_666
C10 N1 C14 116.0(3) . .
C10 N1 Cu1 121.9(2) . .
C14 N1 Cu1 121.4(2) . .
N1 C10 C11 124.1(4) . .
C10 C11 C12 120.1(4) . .
C13 C12 C11 115.8(3) . .
C13 C12 C15B 106.1(6) . .
C11 C12 C15B 138.1(6) . .
C13 C12 C15A 141.9(6) . .
C11 C12 C15A 102.3(6) . .
C15B C12 C15A 36.0(3) . .
C12 C13 C14 120.9(5) . .
N1 C14 C13 123.1(4) . .
C15A C15A C12 112.6(11) 3_856 .
C15B C15B C12 116.5(11) 3_856 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O4 1.9459(18) 4_565
Cu1 O2 1.952(2) .
Cu1 O1 1.9589(19) .
Cu1 N1 2.027(2) .
Cu1 O1W 2.221(2) .
C1 O3 1.217(3) .
C1 O1 1.282(4) .
C1 C2 1.511(4) .
C2 C3 1.509(4) .
C3 O4 1.256(3) .
C3 O2 1.257(4) .
O4 Cu1 1.9459(18) 4_666
N1 C10 1.316(4) .
N1 C14 1.324(4) .
C10 C11 1.370(5) .
C11 C12 1.374(7) .
C12 C13 1.360(8) .
C12 C15B 1.524(9) .
C12 C15A 1.535(10) .
C13 C14 1.377(5) .
C15A C15A 1.34(2) 3_856
C15B C15B 1.28(2) 3_856
