#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:52:35 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179214 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/42/4314249.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_4314249
loop_
_publ_author_name
'Fernando S. Delgado'
'Joaquín Sanchiz'
'Catalina Ruiz-Pérez'
'Francesc Lloret'
'Miguel Julve'
_publ_section_title
;
 Design of High-Dimensional Copper(II) Malonate Complexes with
 Exo-Polydentate N-Donor Ligands
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              5938
_journal_page_last               5948
_journal_paper_doi               10.1021/ic034422w
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C24 H25 Cu2 N3 O11'
_chemical_formula_weight         658.55
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 105.21(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.462(3)
_cell_length_b                   10.275(2)
_cell_length_c                   19.579(4)
_cell_measurement_temperature    293(2)
_cell_volume                     2613.3(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius MACH3'
_diffrn_measurement_method       'ω scan'
_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  0.0707
_diffrn_reflns_av_sigmaI/netI    0.0333
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7899
_diffrn_reflns_theta_full        29.99
_diffrn_reflns_theta_max         29.99
_diffrn_reflns_theta_min         2.53
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rectangular prism'
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.7
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.492
_refine_diff_density_min         -2.412
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     437
_refine_ls_number_reflns         7606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1174P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                5860
_reflns_number_total             7606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic034422wsi20030421_020057.cif
_cod_data_source_block           COMPOUND2
_cod_original_cell_volume        2613.3(9)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4314249
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_assembly
_atom_site_disorder_group
Cu1 Cu 0.49966(2) 0.85329(3) 0.040598(16) 0.01885(10) Uani 1 1 d . . .
Cu2 Cu 0.62599(3) 0.43636(3) 0.166002(18) 0.02425(11) Uani 1 1 d . . .
C1 C 0.4800(2) 0.5238(3) 0.24073(15) 0.0290(6) Uani 1 1 d . . .
C2 C 0.5242(3) 0.6565(3) 0.23251(16) 0.0289(6) Uani 1 1 d . . .
C3 C 0.5333(2) 0.6840(3) 0.15854(14) 0.0218(5) Uani 1 1 d . . .
O1 O 0.52187(18) 0.4250(2) 0.22087(11) 0.0301(4) Uani 1 1 d . . .
O2 O 0.55689(17) 0.5966(2) 0.12115(11) 0.0282(4) Uani 1 1 d . . .
O3 O 0.4077(2) 0.5154(3) 0.26873(16) 0.0508(7) Uani 1 1 d . . .
O4 O 0.51557(15) 0.8004(2) 0.13801(10) 0.0255(4) Uani 1 1 d . . .
C30 C 0.54331(19) 1.1726(3) 0.10279(13) 0.0199(5) Uani 1 1 d . . .
C31 C 0.5741(2) 1.1323(3) 0.17949(15) 0.0253(5) Uani 1 1 d . . .
C32 C 0.6854(2) 1.1717(3) 0.21535(14) 0.0230(5) Uani 1 1 d . . .
O31 O 0.53998(16) 1.28895(19) 0.08492(10) 0.0261(4) Uani 1 1 d . . .
O32 O 0.70893(16) 1.2918(2) 0.21569(11) 0.0280(4) Uani 1 1 d . . .
O33 O 0.52340(14) 1.08089(19) 0.05672(10) 0.0214(4) Uani 1 1 d . . .
O34 O 0.7467(2) 1.0846(2) 0.24163(14) 0.0417(6) Uani 1 1 d . . .
N1 N 0.34271(17) 0.8604(2) 0.03290(13) 0.0252(5) Uani 1 1 d . . .
N2 N 0.65262(16) 0.8325(2) 0.05028(12) 0.0222(4) Uani 1 1 d . . .
N3 N 0.7298(2) 0.4594(2) 0.10875(13) 0.0279(5) Uani 1 1 d . . .
C10 C 0.2706(2) 0.8465(3) -0.02884(16) 0.0271(6) Uani 1 1 d . . .
C11 C 0.1665(2) 0.8427(3) -0.03352(17) 0.0283(6) Uani 1 1 d . . .
C12 C 0.1314(2) 0.8520(3) 0.02669(16) 0.0269(6) Uani 1 1 d . . .
C13 C 0.2059(2) 0.8716(4) 0.09010(17) 0.0377(8) Uani 1 1 d . . .
C14 C 0.3088(2) 0.8758(4) 0.09111(17) 0.0353(7) Uani 1 1 d . . .
C15 C 0.7201(2) 0.8458(3) 0.11399(15) 0.0271(6) Uani 1 1 d . . .
C16 C 0.8249(2) 0.8447(3) 0.12281(16) 0.0308(6) Uani 1 1 d . . .
C17 C 0.8658(2) 0.8333(3) 0.06455(15) 0.0263(6) Uani 1 1 d . . .
C18 C 0.7952(2) 0.8179(3) -0.00128(16) 0.0281(6) Uani 1 1 d . . .
C19 C 0.6912(2) 0.8176(3) -0.00614(15) 0.0259(5) Uani 1 1 d . . .
C20 C 0.0211(2) 0.8416(3) 0.02043(18) 0.0307(6) Uani 1 1 d . . .
C21 C 0.9769(2) 0.8411(3) 0.07373(18) 0.0313(6) Uani 1 1 d . . .
C40 C 0.7010(3) 0.4791(4) 0.03934(18) 0.0352(7) Uani 1 1 d . . .
C41 C 0.7699(3) 0.4925(4) -0.00154(19) 0.0390(7) Uani 1 1 d . . .
C42 C 0.8759(3) 0.4874(3) 0.03121(19) 0.0363(7) Uani 1 1 d . . .
C43 C 0.9051(3) 0.4676(4) 0.1036(2) 0.0380(7) Uani 1 1 d . . .
C44 C 0.8308(3) 0.4534(3) 0.14035(19) 0.0326(6) Uani 1 1 d . . .
C45 C 0.9502(3) 0.5013(4) -0.0117(2) 0.0431(8) Uani 1 1 d . . .
O1W O 0.3582(3) 0.7327(4) 0.34288(17) 0.0690(10) Uani 1 1 d . . .
O2W O 0.1807(4) 0.4831(5) 0.2166(3) 0.1102(17) Uani 1 1 d . . .
O3W O 0.3583(4) 0.2151(5) 0.2216(4) 0.147(3) Uani 1 1 d . . .
H2A H 0.604(3) 0.665(4) 0.2652(19) 0.032(9) Uiso 1 1 d . . .
H2B H 0.494(3) 0.716(4) 0.248(2) 0.043(11) Uiso 1 1 d . . .
H31A H 0.531(3) 1.168(4) 0.2043(19) 0.032(9) Uiso 1 1 d . . .
H31B H 0.566(3) 1.044(3) 0.1844(17) 0.024(8) Uiso 1 1 d . . .
H10 H 0.292(3) 0.841(4) -0.072(2) 0.032(10) Uiso 1 1 d . . .
H11 H 0.124(3) 0.824(4) -0.078(2) 0.041(11) Uiso 1 1 d . . .
H13 H 0.193(3) 0.892(4) 0.1341(18) 0.028(9) Uiso 1 1 d . . .
H14 H 0.357(3) 0.879(3) 0.1315(17) 0.020(8) Uiso 1 1 d . . .
H15 H 0.694(3) 0.856(3) 0.1548(16) 0.018(8) Uiso 1 1 d . . .
H16 H 0.874(3) 0.856(3) 0.1725(17) 0.021(8) Uiso 1 1 d . . .
H18 H 0.816(3) 0.807(4) -0.043(2) 0.041(11) Uiso 1 1 d . . .
H19 H 0.650(3) 0.803(4) -0.053(2) 0.036(10) Uiso 1 1 d . . .
H20 H -0.023(4) 0.826(5) -0.026(2) 0.056(13) Uiso 1 1 d . . .
H21 H 1.011(5) 0.872(5) 0.126(3) 0.082(18) Uiso 1 1 d . . .
H40 H 0.632(4) 0.472(4) 0.019(2) 0.041(11) Uiso 1 1 d . . .
H41 H 0.746(4) 0.518(5) -0.049(2) 0.051(12) Uiso 1 1 d . . .
H43 H 0.970(5) 0.452(5) 0.135(3) 0.070(16) Uiso 1 1 d . . .
H44 H 0.853(3) 0.443(4) 0.182(2) 0.033(10) Uiso 1 1 d . . .
H50 H 0.923(3) 0.513(4) -0.053(2) 0.036(11) 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
_geom_angle_publ_flag
O4 Cu1 O33 175.25(8) . 3_675 ?
O4 Cu1 N2 91.78(9) . . ?
O33 Cu1 N2 91.44(9) 3_675 . ?
O4 Cu1 N1 85.94(9) . . ?
O33 Cu1 N1 91.06(9) 3_675 . ?
N2 Cu1 N1 175.79(10) . . ?
O4 Cu1 O33 99.73(8) . . ?
O33 Cu1 O33 76.79(8) 3_675 . ?
N2 Cu1 O33 89.63(8) . . ?
N1 Cu1 O33 94.24(8) . . ?
O32 Cu2 O2 172.89(9) 1_545 . ?
O32 Cu2 O1 94.49(9) 1_545 . ?
O2 Cu2 O1 88.42(8) . . ?
O32 Cu2 N3 88.71(10) 1_545 . ?
O2 Cu2 N3 88.24(9) . . ?
O1 Cu2 N3 176.50(9) . . ?
O32 Cu2 O31 87.77(8) 1_545 1_545 ?
O2 Cu2 O31 98.63(9) . 1_545 ?
O1 Cu2 O31 92.08(9) . 1_545 ?
N3 Cu2 O31 89.45(9) . 1_545 ?
O3 C1 O1 122.9(3) . . ?
O3 C1 C2 119.1(3) . . ?
O1 C1 C2 117.9(3) . . ?
C3 C2 C1 113.8(3) . . ?
O2 C3 O4 123.3(2) . . ?
O2 C3 C2 121.5(3) . . ?
O4 C3 C2 115.2(2) . . ?
C1 O1 Cu2 123.59(19) . . ?
C3 O2 Cu2 119.96(18) . . ?
C3 O4 Cu1 122.71(19) . . ?
O31 C30 O33 121.5(2) . . ?
O31 C30 C31 121.7(2) . . ?
O33 C30 C31 116.8(2) . . ?
C30 C31 C32 111.3(2) . . ?
O34 C32 O32 124.1(3) . . ?
O34 C32 C31 117.8(3) . . ?
O32 C32 C31 118.1(2) . . ?
C30 O31 Cu2 117.97(17) . 1_565 ?
C32 O32 Cu2 128.60(18) . 1_565 ?
C30 O33 Cu1 112.26(17) . 3_675 ?
C30 O33 Cu1 144.52(17) . . ?
Cu1 O33 Cu1 103.21(8) 3_675 . ?
C14 N1 C10 116.7(2) . . ?
C14 N1 Cu1 120.48(19) . . ?
C10 N1 Cu1 122.79(19) . . ?
C15 N2 C19 117.4(2) . . ?
C15 N2 Cu1 119.90(18) . . ?
C19 N2 Cu1 122.40(18) . . ?
C40 N3 C44 117.9(3) . . ?
C40 N3 Cu2 121.8(2) . . ?
C44 N3 Cu2 120.3(2) . . ?
N1 C10 C11 122.9(3) . . ?
C10 C11 C12 120.6(3) . . ?
C11 C12 C13 116.3(3) . . ?
C11 C12 C20 119.3(3) . . ?
C13 C12 C20 124.3(3) . . ?
C14 C13 C12 120.2(3) . . ?
N1 C14 C13 123.1(3) . . ?
N2 C15 C16 122.5(3) . . ?
C15 C16 C17 120.6(3) . . ?
C18 C17 C16 116.5(2) . . ?
C18 C17 C21 123.1(3) . . ?
C16 C17 C21 120.3(3) . . ?
C19 C18 C17 119.8(3) . . ?
N2 C19 C18 123.1(3) . . ?
C21 C20 C12 126.0(3) 1_455 . ?
C20 C21 C17 123.9(3) 1_655 . ?
N3 C40 C41 123.2(3) . . ?
C40 C41 C42 119.2(3) . . ?
C43 C42 C41 117.1(3) . . ?
C43 C42 C45 123.1(3) . . ?
C41 C42 C45 119.8(3) . . ?
C42 C43 C44 119.9(3) . . ?
N3 C44 C43 122.6(3) . . ?
C45 C45 C42 126.3(5) 3_765 . ?
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 O4 1.940(2) . ?
Cu1 O33 1.9683(19) 3_675 ?
Cu1 N2 2.029(2) . ?
Cu1 N1 2.080(2) . ?
Cu1 O33 2.370(2) . ?
Cu2 O32 1.957(2) 1_545 ?
Cu2 O2 1.979(2) . ?
Cu2 O1 1.980(2) . ?
Cu2 N3 2.022(3) . ?
Cu2 O31 2.278(2) 1_545 ?
C1 O3 1.239(4) . ?
C1 O1 1.271(4) . ?
C1 C2 1.513(4) . ?
C2 C3 1.511(4) . ?
C3 O2 1.251(3) . ?
C3 O4 1.265(3) . ?
C30 O31 1.243(3) . ?
C30 O33 1.283(3) . ?
C30 C31 1.507(4) . ?
C31 C32 1.533(4) . ?
C32 O34 1.235(4) . ?
C32 O32 1.273(3) . ?
O31 Cu2 2.278(2) 1_565 ?
O32 Cu2 1.957(2) 1_565 ?
O33 Cu1 1.9683(19) 3_675 ?
N1 C14 1.343(4) . ?
N1 C10 1.345(4) . ?
N2 C15 1.344(4) . ?
N2 C19 1.347(3) . ?
N3 C40 1.327(4) . ?
N3 C44 1.339(4) . ?
C10 C11 1.381(4) . ?
C11 C12 1.383(4) . ?
C12 C13 1.391(4) . ?
C12 C20 1.463(4) . ?
C13 C14 1.381(4) . ?
C15 C16 1.376(4) . ?
C16 C17 1.395(4) . ?
C17 C18 1.395(4) . ?
C17 C21 1.462(4) . ?
C18 C19 1.378(4) . ?
C20 C21 1.329(4) 1_455 ?
C21 C20 1.329(4) 1_655 ?
C40 C41 1.382(5) . ?
C41 C42 1.403(5) . ?
C42 C43 1.384(5) . ?
C42 C45 1.471(5) . ?
C43 C44 1.384(4) . ?
C45 C45 1.299(8) 3_765 ?
