#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:08:02 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179558 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/27/4502736.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_4502736
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            'C10 H29 Cu2 N3 O14'
_chemical_formula_weight         542.44
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      11
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.224(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2175(10)
_cell_length_b                   17.536(2)
_cell_length_c                   7.9630(10)
_cell_measurement_temperature    293(2)
_cell_volume                     1001.9(2)
_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_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 0.970
_diffrn_measured_fraction_theta_max 0.970
_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  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6152
_diffrn_reflns_theta_full        30.13
_diffrn_reflns_theta_max         30.13
_diffrn_reflns_theta_min         6.42
_exptl_absorpt_coefficient_mu    2.197
_exptl_absorpt_correction_T_max  0.541
_exptl_absorpt_correction_T_min  0.468
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2953
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0515
_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)+(0.0390P)²+2.5157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1250
_reflns_number_gt                2219
_reflns_number_total             2953
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg200675u_si_005.cif
_cod_data_source_block           compound4
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4502736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
Cu1 Cu 0.0000 0.5000 0.0000 0.02841(17) Uani 1 2 d S
Cu2 Cu 0.16557(8) 0.2500 0.10403(8) 0.02718(17) Uani 1 2 d S
N21 N -0.0279(6) 0.2500 0.2627(6) 0.0356(10) Uani 1 2 d S
H21 H -0.0143 0.2084 0.3292 0.043 Uiso 0.50 1 calc PR
H22 H -0.0143 0.2916 0.3292 0.043 Uiso 0.50 1 calc PR
N22 N -0.0467(7) 0.2500 -0.0750(7) 0.098(3) Uani 1 2 d S
H27 H -0.0467 0.1981 -0.0750 0.118 Uiso 0.50 1 calc PR
N23 N 0.3149(6) 0.2500 -0.0945(7) 0.0455(13) Uani 1 2 d S
H32 H 0.3886 0.2915 -0.0898 0.055 Uiso 0.50 1 calc PR
H33 H 0.3886 0.2085 -0.0898 0.055 Uiso 0.50 1 calc PR
O1 O 0.1234(3) 0.40778(14) 0.0865(3) 0.0316(6) Uani 1 1 d .
O2 O 0.2226(4) 0.56091(15) 0.0588(4) 0.0396(7) Uani 1 1 d .
O1W O 0.1318(4) 0.47219(18) -0.2750(4) 0.0427(7) Uani 1 1 d .
O3 O 0.3332(4) 0.33821(14) 0.2350(3) 0.0337(6) Uani 1 1 d .
O2W O 0.5778(5) 0.3316(2) 0.5312(4) 0.0534(8) Uani 1 1 d .
O4 O 0.5139(4) 0.58112(18) 0.1560(5) 0.0598(10) Uani 1 1 d .
O3W O 0.0842(4) 0.60475(19) -0.4690(4) 0.0495(8) Uani 1 1 d .
C1 C 0.2698(5) 0.4019(2) 0.1861(4) 0.0276(7) Uani 1 1 d .
C2 C 0.3726(6) 0.4719(2) 0.2566(5) 0.0413(10) Uani 1 1 d .
H3A H 0.3216 0.4858 0.3601 0.050 Uiso 1 1 calc R
H3B H 0.5017 0.4577 0.2872 0.050 Uiso 1 1 calc R
C3 C 0.3707(5) 0.54214(19) 0.1476(5) 0.0303(7) Uani 1 1 d .
C21 C -0.2098(11) 0.2500 0.1709(11) 0.136(6) Uani 1 2 d S
H23 H -0.2763 0.2946 0.2046 0.163 Uiso 0.50 1 calc PR
H24 H -0.2763 0.2054 0.2046 0.163 Uiso 0.50 1 calc PR
C22 C -0.2169(7) 0.2500 -0.0097(8) 0.0391(13) Uani 1 2 d S
H25 H -0.2863 0.2054 -0.0525 0.047 Uiso 0.50 1 calc PR
H26 H -0.2863 0.2946 -0.0525 0.047 Uiso 0.50 1 calc PR
C23 C -0.0008(9) 0.2500 -0.2293(8) 0.073(3) Uani 1 2 d S
H28 H -0.0575 0.2945 -0.2863 0.088 Uiso 0.50 1 calc PR
H29 H -0.0575 0.2055 -0.2863 0.088 Uiso 0.50 1 calc PR
C24 C 0.1925(8) 0.2500 -0.2548(7) 0.0447(14) Uani 1 2 d S
H30 H 0.2191 0.2947 -0.3198 0.054 Uiso 0.50 1 calc PR
H31 H 0.2191 0.2053 -0.3198 0.054 Uiso 0.50 1 calc PR
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
O1 Cu1 O1 180.0 3_565 .
O1 Cu1 O2 87.89(10) 3_565 .
O1 Cu1 O2 92.11(10) . .
O1 Cu1 O2 92.11(10) 3_565 3_565
O1 Cu1 O2 87.89(10) . 3_565
O2 Cu1 O2 180.0 . 3_565
N22 Cu2 N21 85.1(2) . .
N22 Cu2 N23 82.7(2) . .
N21 Cu2 N23 167.8(2) . .
N22 Cu2 O3 134.25(6) . .
N21 Cu2 O3 95.10(13) . .
N23 Cu2 O3 93.41(12) . .
N22 Cu2 O3 134.25(6) . 4_565
N21 Cu2 O3 95.10(13) . 4_565
N23 Cu2 O3 93.41(12) . 4_565
O3 Cu2 O3 91.41(13) . 4_565
C21 N21 Cu2 110.2(4) . .
C23 N22 C22 132.7(6) . .
C23 N22 Cu2 115.0(4) . .
C22 N22 Cu2 112.3(4) . .
C24 N23 Cu2 111.1(3) . .
C1 O1 Cu1 128.1(2) . .
C3 O2 Cu1 128.4(2) . .
C1 O3 Cu2 108.8(2) . .
O3 C1 O1 121.6(3) . .
O3 C1 C2 117.4(3) . .
O1 C1 C2 121.0(3) . .
C3 C2 C1 118.5(3) . .
O4 C3 O2 122.7(3) . .
O4 C3 C2 117.8(3) . .
O2 C3 C2 119.4(3) . .
N21 C21 C22 116.3(6) . .
N22 C22 C21 116.1(5) . .
N22 C23 C24 118.9(6) . .
C23 C24 N23 112.3(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O1 1.937(2) 3_565
Cu1 O1 1.937(2) .
Cu1 O2 1.944(2) .
Cu1 O2 1.944(2) 3_565
Cu2 N22 1.976(5) .
Cu2 N21 1.982(5) .
Cu2 N23 2.008(5) .
Cu2 O3 2.161(2) .
Cu2 O3 2.161(2) 4_565
N21 C21 1.432(9) .
N22 C23 1.307(9) .
N22 C22 1.385(8) .
N23 C24 1.471(8) .
O1 C1 1.254(4) .
O2 C3 1.260(4) .
O3 C1 1.253(4) .
O4 C3 1.235(4) .
C1 C2 1.510(5) .
C2 C3 1.506(5) .
C21 C22 1.434(11) .
C23 C24 1.431(9) .
