#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/71/2017168.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_2017168
loop_
_publ_author_name
'Chippindale, Ann M.'
'Hibble, Simon J.'
'Bilbé, Edward J.'
_publ_section_title
;
 Dicopper(II) trihydroxide cyanoureate dihydrate
;
_journal_coeditor_code           EM3026
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              i39
_journal_page_last               i41
_journal_paper_doi               10.1107/S0108270109020885
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          '[Cu2 (C2 H2 N3 O) (O H)3] , 2H2 O'
_chemical_formula_moiety         'C2 H5 Cu2 N3 O4 , 2H2 O'
_chemical_formula_sum            'C2 H9 Cu2 N3 O6'
_chemical_formula_weight         298.22
_chemical_name_common
'Dicopper(II) trihydroxide cyanoureate dihydrate'
_chemical_name_systematic
;
Poly[[μ-cyanoureato-tri-μ-hydroxido-dicopper(II)] dihydrate]
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 103.269(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4648(5)
_cell_length_b                   6.3096(2)
_cell_length_c                   10.6032(5)
_cell_measurement_reflns_used    6870
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      32
_cell_measurement_theta_min      5
_cell_volume                     811.66(6)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_data_collection       'Xcalibur (Oxford Diffraction, 2006)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al.,  1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al.,  2003)'
_computing_structure_solution    'SIR92 (Altomare et al.,  1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device       'Oxford Diffraction Xcalibur'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur area-detector'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.028
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6870
_diffrn_reflns_theta_full        29.314
_diffrn_reflns_theta_max         32.572
_diffrn_reflns_theta_min         3.358
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.245
_exptl_absorpt_correction_T_max  0.73
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            blue-green
_exptl_crystal_density_diffrn    2.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.81
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.1139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.000527
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial (Watkin, 1994; Prince, 1982),
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)],
where Ai are the Chebychev coefficients listed below and x = Fcalc/Fmax
Method = robust weighting (Prince, 1982),
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are: 35.5 -37.7 28.1
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0267
_refine_ls_wR_factor_gt          0.0249
_refine_ls_wR_factor_ref         0.0249
_reflns_number_gt                1731
_reflns_number_total             2688
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            em3026.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017168
_cod_database_fobs_code          2017168
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2
loop_
_atom_site_type_symbol
_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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.007607(19) 0.23275(4) 0.25437(2) 0.0061 Uani 1.0000 . .
Cu Cu2 0.0000 0.5000 0.5000 0.0056 Uani 1.0000 . .
Cu Cu3 0.0000 0.0000 0.5000 0.0053 Uani 1.0000 . .
O O1 0.08154(11) 0.2938(2) 0.61558(15) 0.0058 Uani 1.0000 . .
O O2 0.06983(14) -0.0258(2) 0.34803(17) 0.0066 Uani 1.0000 . .
O O3 -0.06870(12) 0.2500(2) 0.39781(15) 0.0056 Uani 1.0000 . .
O O4 0.30960(11) 0.2882(3) 0.66427(16) 0.0155 Uani 1.0000 . .
O O5 0.29541(14) 0.8486(3) 0.64881(18) 0.0185 Uani 1.0000 . .
O O6 0.29652(13) 0.9384(3) 0.37316(18) 0.0199 Uani 1.0000 . .
N N1 0.48208(16) 0.3833(4) 0.6566(2) 0.0253 Uani 1.0000 . .
N N2 0.34458(14) 0.4518(4) 0.4811(2) 0.0154 Uani 1.0000 . .
N N3 0.14777(17) 0.4720(3) 0.3721(2) 0.0126 Uani 1.0000 . .
C C1 0.37405(16) 0.3694(3) 0.6025(2) 0.0133 Uani 1.0000 . .
C C2 0.23926(17) 0.4572(4) 0.4272(2) 0.0107 Uani 1.0000 . .
H H1 0.1498(9) 0.317(5) 0.637(3) 0.011(6) Uiso 1.0000 . .
H H2 0.1390(9) -0.039(5) 0.361(3) 0.014(7) Uiso 1.0000 . .
H H3 -0.1375(9) 0.235(5) 0.375(3) 0.021(8) Uiso 1.0000 . .
H H4 0.504(2) 0.311(5) 0.725(2) 0.0300 Uiso 1.0000 . .
H H5 0.526(2) 0.433(6) 0.614(3) 0.0300 Uiso 1.0000 . .
H H6 0.307(2) 0.829(5) 0.5742(15) 0.0240 Uiso 1.0000 . .
H H7 0.296(3) 0.9814(17) 0.659(4) 0.0240 Uiso 1.0000 . .
H H8 0.315(3) 1.053(3) 0.342(3) 0.0240 Uiso 1.0000 . .
H H9 0.310(3) 0.845(4) 0.321(3) 0.0240 Uiso 1.0000 . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu 0.3201 1.2651 'International Tables Vol C 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_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N3 Cu1 O2 3_545 . 3_555 89.58(6) yes
N3 Cu1 O1 3_545 . 4_554 88.94(6) yes
O2 Cu1 O1 3_555 . 4_554 84.62(7) yes
N3 Cu1 O2 3_545 . . 84.20(6) yes
O2 Cu1 O2 3_555 . . 173.67(5) yes
O1 Cu1 O2 4_554 . . 96.40(7) yes
N3 Cu1 O3 3_545 . . 89.92(6) yes
O2 Cu1 O3 3_555 . . 96.85(7) yes
O1 Cu1 O3 4_554 . . 178.14(6) yes
O2 Cu1 O3 . . . 82.01(7) yes
N3 Cu1 N3 3_545 . . 179.15(2) yes
O2 Cu1 N3 3_555 . . 90.36(7) yes
O1 Cu1 N3 4_554 . . 91.90(7) yes
O2 Cu1 N3 . . . 95.84(7) yes
O3 Cu1 N3 . . . 89.24(7) yes
N3 Cu2 O3 2_566 . 2_566 85.88(7) no
N3 Cu2 O1 2_566 . 2_566 87.18(7) no
O3 Cu2 O1 2_566 . 2_566 84.76(6) no
N3 Cu2 O1 2_566 . . 92.82(7) yes
O3 Cu2 O1 2_566 . . 95.24(6) yes
O1 Cu2 O1 2_566 . . 180 yes
N3 Cu2 O3 2_566 . . 94.12(7) yes
O3 Cu2 O3 2_566 . . 180 yes
O1 Cu2 O3 2_566 . . 95.24(6) no
O1 Cu2 O3 . . . 84.76(6) yes
N3 Cu2 N3 2_566 . . 180 yes
O3 Cu2 N3 2_566 . . 94.12(7) no
O1 Cu2 N3 2_566 . . 92.82(7) no
O1 Cu2 N3 . . . 87.18(7) yes
O3 Cu2 N3 . . . 85.88(7) yes
O1 Cu3 O2 2_556 . 2_556 105.69(6) no
O1 Cu3 O3 2_556 . 2_556 74.73(6) no
O2 Cu3 O3 2_556 . 2_556 80.73(6) no
O1 Cu3 O1 2_556 . . 180 yes
O2 Cu3 O1 2_556 . . 74.31(6) yes
O3 Cu3 O1 2_556 . . 105.27(6) yes
O1 Cu3 O2 2_556 . . 74.31(6) no
O2 Cu3 O2 2_556 . . 180 yes
O3 Cu3 O2 2_556 . . 99.27(6) yes
O1 Cu3 O2 . . . 105.69(6) yes
O1 Cu3 O3 2_556 . . 105.27(6) no
O2 Cu3 O3 2_556 . . 99.27(6) no
O3 Cu3 O3 2_556 . . 180 yes
O1 Cu3 O3 . . . 74.73(6) yes
O2 Cu3 O3 . . . 80.73(6) yes
Cu3 O1 Cu1 . . 4_555 96.09(6) yes
Cu3 O1 Cu2 . . . 95.80(6) yes
Cu1 O1 Cu2 4_555 . . 105.87(7) yes
Cu3 O1 H1 . . . 125(2) no
Cu1 O1 H1 4_555 . . 116.(2) no
Cu2 O1 H1 . . . 114.(2) no
Cu3 O2 Cu1 . . 3_545 104.78(8) yes
Cu3 O2 Cu1 . . . 98.30(7) yes
Cu1 O2 Cu1 3_545 . . 105.85(8) yes
Cu3 O2 H2 . . . 120(2) no
Cu1 O2 H2 3_545 . . 111(2) no
Cu1 O2 H2 . . . 116(2) no
Cu2 O3 Cu3 . . . 104.69(6) yes
Cu2 O3 Cu1 . . . 103.87(7) yes
Cu3 O3 Cu1 . . . 98.77(7) yes
Cu2 O3 H3 . . . 122(2) no
Cu3 O3 H3 . . . 111(2) no
Cu1 O3 H3 . . . 114(2) no
H6 O5 H7 . . . 106(3) no
H8 O6 H9 . . . 103(3) no
C1 N1 H4 . . . 115(2) no
C1 N1 H5 . . . 120(2) no
H4 N1 H5 . . . 122(3) no
C1 N2 C2 . . . 116.8(2) yes
Cu1 N3 Cu2 . . . 78.03(6) no
Cu1 N3 Cu1 . . 3_555 76.72(6) no
Cu2 N3 Cu1 . . 3_555 72.03(6) no
Cu1 N3 C2 . . . 135.90(18) yes
Cu2 N3 C2 . . . 119.21(19) yes
Cu1 N3 C2 3_555 . . 145.31(18) yes
N2 C1 N1 . . . 114.0(2) yes
N2 C1 O4 . . . 125.73(18) yes
N1 C1 O4 . . . 120.3(2) yes
N2 C2 N3 . . . 174.7(3) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 4_554 1.9145(17) yes
Cu1 O2 . . 1.9736(16) yes
Cu1 O2 . 3_555 1.9877(16) yes
Cu1 O3 . . 1.9733(17) yes
Cu1 N3 . . 2.426(2) yes
Cu1 N3 . 3_545 2.658(2) yes
Cu2 O1 . . 1.9119(14) yes
Cu2 O1 . 2_566 1.9119(14) no
Cu2 O3 . . 1.9925(14) yes
Cu2 O3 . 2_566 1.9925(14) no
Cu2 N3 . . 2.532(2) yes
Cu2 N3 . 2_566 2.532(2) no
Cu3 O1 . . 2.3238(15) yes
Cu3 O1 . 2_556 2.3238(15) no
Cu3 O2 . . 2.0061(18) yes
Cu3 O2 . 2_556 2.0061(18) no
Cu3 O3 . . 1.9923(15) yes
Cu3 O3 . 2_556 1.9923(15) no
O1 H1 . . 0.841(9) no
O2 H2 . . 0.846(9) no
O3 H3 . . 0.841(9) no
O4 C1 . . 1.256(3) yes
O5 H6 . . 0.845(10) no
O5 H7 . . 0.844(9) no
O6 H8 . . 0.850(10) no
O6 H9 . . 0.85(3) no
N1 C1 . . 1.340(3) yes
N1 H4 . . 0.846(10) no
N1 H5 . . 0.85(3) no
N2 C1 . . 1.359(3) yes
N2 C2 . . 1.307(3) yes
N3 C2 . . 1.159(3) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 O4 . . . 0.841(9) 1.954(14) 2.770(2) 163(3) yes
O2 H2 O6 . . 1_545 0.846(9) 1.943(14) 2.786(2) 175 yes
O3 H3 O5 . . 2_566 0.841(9) 1.997(16) 2.824(2) 167 yes
N1 H5 N2 . . 2_666 0.85(3) 2.21(3) 3.055(3) 174 yes
O5 H6 O6 . . . 0.845(10) 2.216(18) 2.980(3) 150(3) yes
O5 H7 O4 . . 1_565 0.844(9) 1.943(11) 2.782(3) 172 yes
O6 H8 O4 . . 4_564 0.849(10) 2.12(3) 2.842(3) 142 yes
O6 H9 O5 . . 4_564 0.85(3) 2.17(3) 2.987(3) 161 yes
