#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/81/2008145.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008145
loop_
_publ_author_name
'Gasque, Laura'
'Moreno-Esparza, Rafael'
'Mollins, Elies'
'Briansó-Penalva, José Luis'
'Ruiz-Ramírez, Lena'
'Medina-Dickinson, Gerardo'
_publ_section_title
;Aqua(5,6-dimethyl-1,10-phenanthroline-N,N')(malonato-O,O')copper(II)
 hydrate
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              158
_journal_page_last               160
_journal_paper_doi               10.1107/S0108270198009937
_journal_volume                  55
_journal_year                    1999
_chemical_formula_iupac          '[Cu (C3 H2 O4) (C14 H12 N2) (H2 O)], H2 O'
_chemical_formula_moiety         '(C17 H16 Cu N2 O5), (H2 O)'
_chemical_formula_sum            'C34 H36 Cu2 N4 O12'
_chemical_formula_weight         409.85
_chemical_name_systematic
; (MALONATE)(AQUA)(5,6-DIMETHYL-1,10'PHENANTHROLINE)
  COPPER (II) HYDRATE
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 120.68(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.772(5)
_cell_length_b                   10.165(2)
_cell_length_c                   15.362(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.4
_cell_measurement_theta_min      11.5
_cell_volume                     3326.8(15)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1997)'
_computing_publication_material  'CIFTAB in SHELXS97'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.475
_diffrn_measured_fraction_theta_max 0.475
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            5208
_diffrn_reflns_theta_full        30.41
_diffrn_reflns_theta_max         30.41
_diffrn_reflns_theta_min         2.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.35
_exptl_absorpt_correction_T_max  0.640
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'ψ scan (North et al., 1968)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1688
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .37
_exptl_crystal_size_min          .33
_refine_diff_density_max         0.47
_refine_diff_density_min         -0.82
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         5033
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.056
_refine_ls_R_factor_gt           0.032
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0560P)²+1.6531P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.096
_reflns_number_gt                3946
_reflns_number_total             5033
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1113.cif
_cod_data_source_block           fr1113
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.6531P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0560P)^2^+1.6531P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        3326.8(11)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2008145
loop_
_symmetry_equiv_pos_as_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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
Cu1 0.117278(9) 0.11082(2) 0.397240(15) 0.02948(9) Uani d . 1 . . Cu
O1W 0.17228(7) 0.12441(14) 0.56912(11) 0.0415(3) Uani d D 1 . . O
H1W 0.1913(12) 0.1910(17) 0.592(2) 0.067(4) Uiso d D 1 . . H
H2W 0.1956(12) 0.065(2) 0.595(2) 0.067(4) Uiso d D 1 . . H
O1 0.18422(6) 0.16314(13) 0.37457(11) 0.0406(3) Uani d . 1 . . O
O2 0.12627(6) -0.07371(14) 0.38287(12) 0.0406(3) Uani d . 1 . . O
O3 0.27034(6) 0.12794(13) 0.36942(12) 0.0419(3) Uani d . 1 . . O
O4 0.17238(8) -0.23950(14) 0.35559(15) 0.0573(4) Uani d . 1 . . O
N1 0.08895(6) 0.29872(14) 0.38381(10) 0.0294(3) Uani d . 1 . . N
N2 0.03156(6) 0.08021(14) 0.38044(11) 0.0291(3) Uani d . 1 . . N
C1 0.11957(8) 0.40577(17) 0.38442(13) 0.0347(4) Uani d . 1 . . C
H1 0.1576 0.3970 0.3866 0.035(5) Uiso calc R 1 . . H
C2 0.09618(9) 0.53128(18) 0.38186(14) 0.0385(4) Uani d . 1 . . C
H2 0.1188 0.6051 0.3831 0.054(8) Uiso calc R 1 . . H
C3 0.04001(9) 0.54584(17) 0.37749(14) 0.0368(4) Uani d . 1 . . C
H3 0.0244 0.6297 0.3757 0.034(5) Uiso calc R 1 . . H
C4 0.00550(7) 0.43440(17) 0.37563(12) 0.0296(3) Uani d . 1 . . C
C5 -0.05426(8) 0.43945(18) 0.37116(12) 0.0323(3) Uani d . 1 . . C
C6 -0.08436(7) 0.32544(18) 0.36896(13) 0.0328(3) Uani d . 1 . . C
C7 -0.05662(7) 0.19918(17) 0.37140(12) 0.0296(3) Uani d . 1 . . C
C8 -0.08441(8) 0.07634(19) 0.36727(14) 0.0371(4) Uani d . 1 . . C
H8 -0.1230 0.0732 0.3639 0.051(7) Uiso calc R 1 . . H
C9 -0.05512(8) -0.03788(18) 0.36819(15) 0.0394(4) Uani d . 1 . . C
H9 -0.0739 -0.1186 0.3643 0.048(7) Uiso calc R 1 . . H
C10 0.00324(8) -0.03285(18) 0.37497(14) 0.0361(4) Uani d . 1 . . C
H10 0.0229 -0.1112 0.3757 0.046(7) Uiso calc R 1 . . H
C11 0.00202(7) 0.19338(16) 0.37761(11) 0.0268(3) Uani d . 1 . . C
C12 0.03293(7) 0.31281(15) 0.37936(11) 0.0266(3) Uani d . 1 . . C
C13 0.22871(8) 0.08996(16) 0.38577(13) 0.0312(3) Uani d . 1 . . C
C14 0.23343(9) -0.04808(19) 0.42696(19) 0.0461(5) Uani d . 1 . . C
H14A 0.2513 -0.0417 0.4996 0.104(12) Uiso calc R 1 . . H
H14B 0.2628 -0.0975 0.4157 0.065(8) Uiso calc R 1 . . H
C15 0.17297(8) -0.12674(17) 0.38348(15) 0.0343(3) Uani d . 1 . . C
C51 -0.08165(10) 0.5743(2) 0.36668(16) 0.0430(4) Uani d . 1 . . C
H51A -0.0501 0.6293 0.4185 0.067(8) Uiso calc R 1 . . H
H51B -0.1165 0.5660 0.3772 0.108(13) Uiso calc R 1 . . H
H51C -0.0957 0.6130 0.3016 0.063(8) Uiso calc R 1 . . H
C61 -0.14690(9) 0.3245(2) 0.36208(18) 0.0480(5) Uani d . 1 . . C
H61A -0.1574 0.4121 0.3717 0.121(14) Uiso calc R 1 . . H
H61B -0.1451 0.2678 0.4135 0.055(7) Uiso calc R 1 . . H
H61C -0.1783 0.2928 0.2966 0.081(9) Uiso calc R 1 . . H
O2W 0.24522(9) 0.57988(18) 0.32580(12) 0.0556(4) Uani d D 1 . . O
H3W 0.2268(12) 0.650(2) 0.340(2) 0.067(4) Uiso d D 1 . . H
H4W 0.2387(14) 0.595(3) 0.2614(11) 0.067(4) Uiso d D 1 . . H
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O1 95.03(6) y
O2 Cu1 N1 167.06(6) y
O1 Cu1 N1 90.38(6) y
O2 Cu1 N2 90.62(6) y
O1 Cu1 N2 163.17(6) y
N1 Cu1 N2 81.06(5) y
O2 Cu1 O1W 99.05(6) y
O1 Cu1 O1W 97.55(7) y
N1 Cu1 O1W 91.86(5) y
N2 Cu1 O1W 97.19(6) y
C13 O1 Cu1 125.48(12) ?
C15 O2 Cu1 124.97(12) ?
C1 N1 C12 118.65(15) ?
C1 N1 Cu1 127.74(12) ?
C12 N1 Cu1 113.51(10) ?
C10 N2 C11 118.36(15) ?
C10 N2 Cu1 128.79(12) ?
C11 N2 Cu1 112.82(11) ?
N1 C1 C2 121.61(16) ?
C3 C2 C1 119.91(16) ?
C2 C3 C4 120.36(16) ?
C12 C4 C3 115.63(15) ?
C12 C4 C5 119.83(15) ?
C3 C4 C5 124.54(16) ?
C6 C5 C4 120.14(16) ?
C6 C5 C51 122.61(16) ?
C4 C5 C51 117.24(16) ?
C5 C6 C7 120.31(15) ?
C5 C6 C61 122.53(17) ?
C7 C6 C61 117.15(16) ?
C11 C7 C8 115.39(15) ?
C11 C7 C6 119.93(15) ?
C8 C7 C6 124.68(15) ?
C9 C8 C7 120.49(16) ?
C8 C9 C10 119.61(16) ?
N2 C10 C9 122.03(17) ?
N2 C11 C7 124.10(15) ?
N2 C11 C12 116.51(14) ?
C7 C11 C12 119.37(15) ?
N1 C12 C4 123.84(14) ?
N1 C12 C11 115.75(14) ?
C4 C12 C11 120.41(14) ?
O3 C13 O1 123.04(16) ?
O3 C13 C14 118.45(16) ?
O1 C13 C14 118.42(15) ?
C13 C14 C15 117.00(16) ?
O4 C15 O2 123.17(17) ?
O4 C15 C14 118.75(17) ?
O2 C15 C14 117.97(16) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 . 1.9150(10) y
Cu1 O1 . 1.9350(10) y
Cu1 N1 . 2.009(2) y
Cu1 N2 . 2.0280(10) y
Cu1 O1W . 2.275(2) y
O1 C13 . 1.266(2) ?
O2 C15 . 1.272(2) ?
O3 C13 . 1.241(2) ?
O4 C15 . 1.221(2) ?
N1 C1 . 1.324(2) ?
N1 C12 . 1.362(2) ?
N2 C10 . 1.326(2) ?
N2 C11 . 1.352(2) ?
C1 C2 . 1.393(3) ?
C2 C3 . 1.367(3) ?
C3 C4 . 1.411(2) ?
C4 C12 . 1.397(2) ?
C4 C5 . 1.448(2) ?
C5 C6 . 1.369(3) ?
C5 C51 . 1.515(3) ?
C6 C7 . 1.447(2) ?
C6 C61 . 1.498(2) ?
C7 C11 . 1.408(2) ?
C7 C8 . 1.412(2) ?
C8 C9 . 1.365(3) ?
C9 C10 . 1.397(2) ?
C11 C12 . 1.428(2) ?
C13 C14 . 1.519(3) ?
C14 C15 . 1.519(3) ?
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_publ_flag
O2 Cu1 O1 C13 -21.46(16) ?
N1 Cu1 O1 C13 170.30(15) ?
N2 Cu1 O1 C13 -130.66(19) ?
O1W Cu1 O1 C13 78.38(16) ?
O1 Cu1 O2 C15 13.93(17) ?
N1 Cu1 O2 C15 128.4(2) ?
N2 Cu1 O2 C15 178.06(16) ?
O1W Cu1 O2 C15 -84.56(17) ?
O2 Cu1 N1 C1 -128.3(2) ?
O1 Cu1 N1 C1 -13.36(15) ?
N2 Cu1 N1 C1 -178.80(16) ?
O1W Cu1 N1 C1 84.21(15) ?
O2 Cu1 N1 C12 55.6(3) ?
O1 Cu1 N1 C12 170.52(11) ?
N2 Cu1 N1 C12 5.08(11) ?
O1W Cu1 N1 C12 -91.91(12) ?
O2 Cu1 N2 C10 6.83(16) ?
O1 Cu1 N2 C10 116.6(2) ?
N1 Cu1 N2 C10 176.88(16) ?
O1W Cu1 N2 C10 -92.37(16) ?
O2 Cu1 N2 C11 -175.13(12) ?
O1 Cu1 N2 C11 -65.3(2) ?
N1 Cu1 N2 C11 -5.09(11) ?
O1W Cu1 N2 C11 85.67(11) ?
C12 N1 C1 C2 0.8(3) ?
Cu1 N1 C1 C2 -175.17(13) ?
N1 C1 C2 C3 -0.7(3) ?
C1 C2 C3 C4 0.0(3) ?
C2 C3 C4 C12 0.5(2) ?
C2 C3 C4 C5 179.93(17) ?
C12 C4 C5 C6 -1.0(2) ?
C3 C4 C5 C6 179.55(16) ?
C12 C4 C5 C51 -179.68(15) ?
C3 C4 C5 C51 0.9(2) ?
C4 C5 C6 C7 0.2(2) ?
C51 C5 C6 C7 178.75(16) ?
C4 C5 C6 C61 -178.64(17) ?
C51 C5 C6 C61 -0.1(3) ?
C5 C6 C7 C11 1.0(2) ?
C61 C6 C7 C11 179.87(16) ?
C5 C6 C7 C8 -178.58(17) ?
C61 C6 C7 C8 0.3(3) ?
C11 C7 C8 C9 -0.8(2) ?
C6 C7 C8 C9 178.81(17) ?
C7 C8 C9 C10 1.1(3) ?
C11 N2 C10 C9 -1.1(3) ?
Cu1 N2 C10 C9 176.84(14) ?
C8 C9 C10 N2 -0.1(3) ?
C10 N2 C11 C7 1.4(2) ?
Cu1 N2 C11 C7 -176.82(12) ?
C10 N2 C11 C12 -177.42(15) ?
Cu1 N2 C11 C12 4.33(17) ?
C8 C7 C11 N2 -0.5(2) ?
C6 C7 C11 N2 179.90(15) ?
C8 C7 C11 C12 178.31(14) ?
C6 C7 C11 C12 -1.3(2) ?
C1 N1 C12 C4 -0.2(2) ?
Cu1 N1 C12 C4 176.32(12) ?
C1 N1 C12 C11 179.21(14) ?
Cu1 N1 C12 C11 -4.28(17) ?
C3 C4 C12 N1 -0.5(2) ?
C5 C4 C12 N1 -179.90(14) ?
C3 C4 C12 C11 -179.82(15) ?
C5 C4 C12 C11 0.7(2) ?
N2 C11 C12 N1 -0.1(2) y
C7 C11 C12 N1 -178.99(14) ?
N2 C11 C12 C4 179.34(14) ?
C7 C11 C12 C4 0.4(2) ?
Cu1 O1 C13 O3 179.38(13) ?
Cu1 O1 C13 C14 -4.3(2) ?
O3 C13 C14 C15 -139.21(18) ?
O1 C13 C14 C15 44.3(3) y
Cu1 O2 C15 O4 -165.82(16) ?
Cu1 O2 C15 C14 17.9(3) ?
C13 C14 C15 O4 131.5(2) ?
C13 C14 C15 O2 -52.1(3) y
