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#$Date: 2016-03-23 00:56:45 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179136 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/98/4309814.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_4309814
loop_
_publ_author_name
'Jorge Pasán'
'Joaquín Sanchiz'
'Catalina Ruiz-Pérez'
'Francesc Lloret'
'Miguel Julve'
_publ_contact_author_address
;Laboratorio de Rayos X y Materiales Moleculares
Dpto. Fisica Fundamental II
Facultad de Fisica. Universidad de La Laguna
Avda. Astrofisico Francisco Sanchez s/n
38204. La Laguna. Santa Cruz de Tenerife
Spain
;
_publ_contact_author_email       caruiz@ull.es
_publ_contact_author_fax         '+34 922 31 83 20'
_publ_contact_author_name        'Catalina Ruiz-Perez'
_publ_contact_author_phone       '+34 922 31 83 00'
_publ_section_title
;
Polymeric Networks of Copper(II) Phenylmalonate with Heteroaromatic N-donor
Ligands: Synthesis, Crystal Structure, and Magnetic Properties
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7794
_journal_page_last               7801
_journal_paper_doi               10.1021/ic0503986
_journal_volume                  44
_journal_year                    2005
_chemical_formula_sum            'C19 H18 Cu N2 O6'
_chemical_formula_weight         433.86
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.807(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.0837(6)
_cell_length_b                   9.3514(4)
_cell_length_c                   11.0831(8)
_cell_measurement_temperature    293(2)
_cell_volume                     896.35(10)
_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    CRYSTALMAKER
_computing_publication_material  'PARST97 (Nardelli, 1997)'
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8587
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         6.43
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    1.259
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       sheet
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.387(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4940
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.069
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0407P)²+0.3038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0907
_reflns_number_gt                4242
_reflns_number_total             4940
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0503986si20050317_052352_2.cif
_cod_data_source_block           compound1
_cod_database_code               4309814
loop_
_symmetry_equiv_pos_as_xyz
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.09650(3) 0.29629(3) -0.04779(2) 0.02042(8) Uani 1 1 d . . .
O1 O -0.1217(2) 0.7455(2) -0.02063(19) 0.0260(4) Uani 1 1 d . . .
O2 O -0.0506(2) 0.5255(2) -0.04882(19) 0.0284(4) Uani 1 1 d . . .
O3 O -0.5360(3) 0.4438(3) -0.1964(3) 0.0444(6) Uani 1 1 d . . .
O4 O -0.3149(2) 0.33496(19) -0.11493(19) 0.0274(5) Uani 1 1 d . . .
O1W O -0.3672(5) -0.0602(4) -0.0239(3) 0.0834(11) Uani 1 1 d . . .
O2W O 0.3908(6) 0.1234(6) -0.1805(6) 0.1196(19) Uani 1 1 d . . .
N1 N -0.0911(3) 0.2560(2) -0.2274(2) 0.0255(6) Uani 1 1 d . . .
N2 N -0.1113(2) 0.2947(4) -0.86942(17) 0.0254(4) Uani 1 1 d . . .
C1 C -0.1526(4) 0.6183(3) -0.0628(2) 0.0214(5) Uani 1 1 d . . .
C2 C -0.3204(3) 0.5966(3) -0.1394(3) 0.0247(6) Uani 1 1 d . . .
H2 H -0.3810 0.6571 -0.1000 0.030 Uiso 1 1 calc R . .
C3 C -0.3929(3) 0.4462(3) -0.1509(2) 0.0248(6) Uani 1 1 d . . .
C4 C -0.3411(3) 0.6602(3) -0.2711(3) 0.0282(6) Uani 1 1 d . . .
C5 C -0.4076(4) 0.7921(5) -0.3025(3) 0.0439(7) Uani 1 1 d . . .
H5 H -0.4424 0.8425 -0.2442 0.053 Uiso 1 1 calc R . .
C6 C -0.4235(5) 0.8516(5) -0.4224(5) 0.0596(13) Uani 1 1 d . . .
H6 H -0.4679 0.9414 -0.4429 0.071 Uiso 1 1 calc R . .
C7 C -0.3736(5) 0.7774(6) -0.5086(4) 0.0558(13) Uani 1 1 d . . .
H7 H -0.3864 0.8156 -0.5886 0.067 Uiso 1 1 calc R . .
C8 C -0.3050(5) 0.6473(5) -0.4772(4) 0.0511(10) Uani 1 1 d . . .
H8 H -0.2700 0.5973 -0.5357 0.061 Uiso 1 1 calc R . .
C9 C -0.2869(5) 0.5889(4) -0.3582(3) 0.0422(8) Uani 1 1 d . . .
H9 H -0.2379 0.5011 -0.3369 0.051 Uiso 1 1 calc R . .
C10 C -0.2118(4) 0.2044(3) -0.3184(3) 0.0263(6) Uani 1 1 d . . .
H10 H -0.2945 0.1666 -0.2960 0.032 Uiso 1 1 calc R . .
C11 C -0.2190(4) 0.2048(3) -0.4453(3) 0.0257(6) Uani 1 1 d . . .
H11 H -0.3037 0.1650 -0.5058 0.031 Uiso 1 1 calc R . .
C12 C -0.0994(3) 0.2649(3) -0.4814(2) 0.0247(7) Uani 1 1 d . . .
C13 C 0.0264(3) 0.3148(5) -0.3853(3) 0.0370(8) Uani 1 1 d . . .
H13 H 0.1107 0.3534 -0.4048 0.044 Uiso 1 1 calc R . .
C14 C 0.0277(3) 0.3076(5) -0.2610(2) 0.0359(7) Uani 1 1 d . . .
H14 H 0.1146 0.3399 -0.1981 0.043 Uiso 1 1 calc R . .
C15 C -0.1066(3) 0.2760(3) -0.6171(2) 0.0244(6) Uani 1 1 d . . .
C16 C -0.2034(4) 0.1916(3) -0.7095(3) 0.0326(7) Uani 1 1 d . . .
H16 H -0.2686 0.1262 -0.6883 0.039 Uiso 1 1 calc R . .
C17 C -0.2036(4) 0.2041(4) -0.8343(3) 0.0334(7) Uani 1 1 d . . .
H17 H -0.2707 0.1470 -0.8957 0.040 Uiso 1 1 calc R . .
C18 C -0.0180(4) 0.3772(3) -0.7811(3) 0.0315(7) Uani 1 1 d . . .
H18 H 0.0468 0.4409 -0.8047 0.038 Uiso 1 1 calc R . .
C19 C -0.0136(4) 0.3721(4) -0.6554(3) 0.0328(7) Uani 1 1 d . . .
H19 H 0.0517 0.4330 -0.5966 0.039 Uiso 1 1 calc R . .
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 O1 176.69(9) . 2_545 ?
O4 Cu1 N2 90.60(9) . 1_556 ?
O1 Cu1 N2 88.94(9) 2_545 1_556 ?
O4 Cu1 N1 89.26(9) . . ?
O1 Cu1 N1 90.55(9) 2_545 . ?
N2 Cu1 N1 168.70(12) 1_556 . ?
O4 Cu1 O2 89.40(8) . . ?
O1 Cu1 O2 93.90(8) 2_545 . ?
N2 Cu1 O2 94.72(11) 1_556 . ?
N1 Cu1 O2 96.58(8) . . ?
C1 O1 Cu1 116.91(19) . 2 ?
C1 O2 Cu1 123.3(2) . . ?
C3 O4 Cu1 133.89(19) . . ?
C10 N1 C14 117.9(2) . . ?
C10 N1 Cu1 123.1(2) . . ?
C14 N1 Cu1 117.9(2) . . ?
C18 N2 C17 118.1(2) . . ?
C18 N2 Cu1 119.9(2) . 1_554 ?
C17 N2 Cu1 121.8(2) . 1_554 ?
O2 C1 O1 122.1(3) . . ?
O2 C1 C2 124.1(2) . . ?
O1 C1 C2 113.6(2) . . ?
C1 C2 C4 106.9(2) . . ?
C1 C2 C3 120.0(2) . . ?
C4 C2 C3 110.5(2) . . ?
O3 C3 O4 122.3(3) . . ?
O3 C3 C2 114.7(3) . . ?
O4 C3 C2 123.1(3) . . ?
C5 C4 C9 118.7(3) . . ?
C5 C4 C2 120.4(3) . . ?
C9 C4 C2 120.8(3) . . ?
C4 C5 C6 120.3(4) . . ?
C7 C6 C5 120.0(4) . . ?
C6 C7 C8 119.9(4) . . ?
C7 C8 C9 120.3(4) . . ?
C4 C9 C8 120.7(4) . . ?
N1 C10 C11 122.6(3) . . ?
C12 C11 C10 119.7(3) . . ?
C13 C12 C11 116.7(3) . . ?
C13 C12 C15 121.7(3) . . ?
C11 C12 C15 121.6(3) . . ?
C14 C13 C12 120.5(3) . . ?
N1 C14 C13 122.5(3) . . ?
C16 C15 C19 117.0(3) . . ?
C16 C15 C12 122.2(3) . . ?
C19 C15 C12 120.8(2) . . ?
C15 C16 C17 120.0(3) . . ?
N2 C17 C16 122.4(3) . . ?
N2 C18 C19 122.6(3) . . ?
C18 C19 C15 119.9(3) . . ?
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 1.928(2) . ?
Cu1 O1 1.952(2) 2_545 ?
Cu1 N2 2.0220(19) 1_556 ?
Cu1 N1 2.041(2) . ?
Cu1 O2 2.185(2) . ?
O1 C1 1.277(3) . ?
O1 Cu1 1.952(2) 2 ?
O2 C1 1.244(4) . ?
O3 C3 1.243(4) . ?
O4 C3 1.253(4) . ?
N1 C10 1.333(4) . ?
N1 C14 1.335(4) . ?
N2 C18 1.328(4) . ?
N2 C17 1.332(4) . ?
N2 Cu1 2.0220(19) 1_554 ?
C1 C2 1.514(4) . ?
C2 C4 1.533(4) . ?
C2 C3 1.542(4) . ?
C4 C5 1.371(5) . ?
C4 C9 1.381(5) . ?
C5 C6 1.407(6) . ?
C6 C7 1.365(7) . ?
C7 C8 1.363(7) . ?
C8 C9 1.390(5) . ?
C10 C11 1.387(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.384(4) . ?
C12 C15 1.488(3) . ?
C13 C14 1.375(4) . ?
C15 C16 1.377(4) . ?
C15 C19 1.386(4) . ?
C16 C17 1.387(4) . ?
C18 C19 1.382(4) . ?
