#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/17/2211717.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_2211717
loop_
_publ_author_name
'Li, Na'
'Wei, Qing'
_publ_section_title
;catena-Poly[[[aqua(2-amino-4,6-dimethylpyrimidine-κN¹)copper(II)]-μ-benzene-1,3-dicarboxylato-κ²O¹:O³]
 2-amino-4,6-dimethylpyrimidine solvate]
;
_journal_coeditor_code           BH2061
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m184
_journal_page_last               m186
_journal_paper_doi               10.1107/S1600536806052688
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C8 H4 O4) (C6 H9 N3) (H2 O)], C6 H9 N3'
_chemical_formula_moiety         'C14 H15 Cu1 N3 O5, C6 H9 N3'
_chemical_formula_sum            'C20 H24 Cu N6 O5'
_chemical_formula_weight         491.99
_chemical_name_systematic
;
catena-Poly[[[aqua(2-amino-4,6-dimethylpyrimidine-\kN¹)copper(II)]-
μ-benzene-1,3-dicarboxylato-κ²O¹:O³] 2-amino-4,6-dimethylpyrimidine
solvate]
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 97.195(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.8409(2)
_cell_length_b                   21.4009(7)
_cell_length_c                   13.1791(3)
_cell_measurement_reflns_used    3900
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.79
_cell_volume                     2194.07(10)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'SHELXTL(Bruker, 2005)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART APEX-II area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9167
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.79
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.040
_exptl_absorpt_correction_T_max  0.8766
_exptl_absorpt_correction_T_min  0.6933
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1020
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.543
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0452
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0981P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1488
_reflns_number_gt                2923
_reflns_number_total             3900
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2061.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C20 H24 Cu1 N6 O5'
_cod_database_code               2211717
_cod_database_fobs_code          2211717
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_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Cu Cu1 0.56712(5) 0.09899(2) 0.66860(3) 0.03712(19) Uani d . 1
C C1 0.2411(4) 0.21107(16) 0.7969(2) 0.0326(7) Uani d . 1
C C2 0.2750(4) 0.25289(16) 0.8778(2) 0.0332(8) Uani d . 1
H H2 0.3878 0.2595 0.9069 0.040 Uiso calc R 1
C C3 0.1438(4) 0.28457(16) 0.9151(2) 0.0326(8) Uani d . 1
C C4 -0.0248(5) 0.27449(19) 0.8724(3) 0.0429(9) Uani d . 1
H H4 -0.1142 0.2951 0.8987 0.052 Uiso calc R 1
C C5 -0.0605(5) 0.2336(2) 0.7903(3) 0.0491(10) Uani d . 1
H H5 -0.1733 0.2274 0.7608 0.059 Uiso calc R 1
C C6 0.0720(5) 0.20242(18) 0.7531(3) 0.0421(9) Uani d . 1
H H6 0.0483 0.1753 0.6981 0.051 Uiso calc R 1
C C7 0.3838(4) 0.17441(17) 0.7599(3) 0.0367(8) Uani d . 1
C C8 0.1854(5) 0.32871(17) 1.0033(3) 0.0390(8) Uani d . 1
C C12 0.4664(4) -0.02542(17) 0.7290(2) 0.0369(8) Uani d . 1
C C10 0.5874(5) -0.07974(18) 0.8781(3) 0.0427(9) Uani d . 1
N N2 0.6616(4) -0.02807(15) 0.9154(2) 0.0421(7) Uani d . 1
C C9 0.6375(4) 0.02455(17) 0.8607(2) 0.0368(8) Uani d . 1
C C13 0.6167(7) -0.1377(2) 0.9390(3) 0.0638(12) Uani d . 1
H H13A 0.7022 -0.1301 0.9965 0.096 Uiso calc R 1
H H13B 0.6557 -0.1701 0.8971 0.096 Uiso calc R 1
H H13C 0.5113 -0.1504 0.9629 0.096 Uiso calc R 1
N N3 0.7086(5) 0.07697(15) 0.8994(2) 0.0514(9) Uani d . 1
H H3A 0.7689 0.0767 0.9586 0.062 Uiso calc R 1
H H3B 0.6945 0.1112 0.8653 0.062 Uiso calc R 1
C C15 0.9360(5) 0.02829(18) 0.1679(3) 0.0409(9) Uani d . 1
C C16 1.0695(5) 0.08408(19) 0.3043(3) 0.0416(9) Uani d . 1
C C17 1.0308(5) 0.13806(19) 0.2519(3) 0.0463(9) Uani d . 1
H H17 1.0612 0.1766 0.2813 0.056 Uiso calc R 1
C C18 0.9445(5) 0.13412(18) 0.1533(3) 0.0425(9) Uani d . 1
C C19 0.8990(7) 0.1917(2) 0.0906(3) 0.0650(13) Uani d . 1
H H19A 0.9437 0.1881 0.0262 0.097 Uiso calc R 1
H H19B 0.9481 0.2277 0.1266 0.097 Uiso calc R 1
H H19C 0.7763 0.1960 0.0787 0.097 Uiso calc R 1
C C20 1.1605(6) 0.0833(2) 0.4116(3) 0.0602(12) Uani d . 1
H H20A 1.1147 0.0504 0.4495 0.090 Uiso calc R 1
H H20B 1.1439 0.1227 0.4439 0.090 Uiso calc R 1
H H20C 1.2811 0.0764 0.4099 0.090 Uiso calc R 1
N N1 0.5485(4) 0.02706(13) 0.76478(19) 0.0334(6) Uani d . 1
C C11 0.4813(5) -0.07939(19) 0.7839(3) 0.0465(10) Uani d . 1
H H11 0.4227 -0.1152 0.7597 0.056 Uiso calc R 1
C C14 0.3609(5) -0.0202(2) 0.6267(3) 0.0506(10) Uani d . 1
H H14A 0.2787 0.0129 0.6281 0.076 Uiso calc R 1
H H14B 0.3015 -0.0589 0.6106 0.076 Uiso calc R 1
H H14C 0.4347 -0.0114 0.5756 0.076 Uiso calc R 1
N N4 0.8973(4) 0.07929(15) 0.1114(2) 0.0401(7) Uani d . 1
N N5 1.0254(4) 0.02806(15) 0.2635(2) 0.0426(8) Uani d . 1
N N6 0.8844(5) -0.02695(17) 0.1279(3) 0.0617(10) Uani d . 1
H H6A 0.8282 -0.0288 0.0676 0.074 Uiso calc R 1
H H6B 0.9074 -0.0606 0.1624 0.074 Uiso calc R 1
O O1 0.3448(3) 0.13265(12) 0.69321(18) 0.0420(6) Uani d . 1
O O2 0.5372(3) 0.18595(12) 0.7953(2) 0.0457(6) Uani d . 1
O O3 0.3390(3) 0.34437(15) 1.0266(2) 0.0614(9) Uani d . 1
O O4 0.0599(3) 0.34829(13) 1.04698(19) 0.0452(6) Uani d . 1
O O5 0.8004(4) 0.07415(18) 0.6585(3) 0.0730(10) Uani d D 1
H H5E 0.880(6) 0.048(2) 0.662(5) 0.12(2) Uiso d D 1
H H5F 0.847(6) 0.091(2) 0.611(3) 0.070(16) Uiso d D 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 Cu1 O1 . . 171.91(15) yes
O5 Cu1 O4 . 4_665 91.88(12) yes
O1 Cu1 O4 . 4_665 89.34(11) yes
O5 Cu1 N1 . . 88.67(13) yes
O1 Cu1 N1 . . 92.35(11) yes
O4 Cu1 N1 4_665 . 164.05(11) yes
O5 Cu1 O2 . . 114.60(15) yes
O1 Cu1 O2 . . 57.32(9) yes
O4 Cu1 O2 4_665 . 96.94(10) yes
N1 Cu1 O2 . . 97.31(10) yes
C6 C1 C2 . . 118.9(3) ?
C6 C1 C7 . . 120.5(3) ?
C2 C1 C7 . . 120.5(3) ?
C3 C2 C1 . . 120.8(3) ?
C3 C2 H2 . . 119.6 ?
C1 C2 H2 . . 119.6 ?
C2 C3 C4 . . 119.7(3) ?
C2 C3 C8 . . 119.2(3) ?
C4 C3 C8 . . 121.0(3) ?
C3 C4 C5 . . 120.1(3) ?
C3 C4 H4 . . 119.9 ?
C5 C4 H4 . . 119.9 ?
C6 C5 C4 . . 119.6(3) ?
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 120.7(3) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
O2 C7 O1 . . 122.2(3) ?
O2 C7 C1 . . 119.7(3) ?
O1 C7 C1 . . 118.1(3) ?
O3 C8 O4 . . 125.2(3) ?
O3 C8 C3 . . 117.9(3) ?
O4 C8 C3 . . 116.9(3) ?
N1 C12 C11 . . 121.0(3) ?
N1 C12 C14 . . 116.0(3) ?
C11 C12 C14 . . 122.9(3) ?
N2 C10 C11 . . 120.7(3) ?
N2 C10 C13 . . 118.0(3) ?
C11 C10 C13 . . 121.2(4) ?
C10 N2 C9 . . 118.7(3) ?
N3 C9 N2 . . 118.7(3) ?
N3 C9 N1 . . 117.6(3) ?
N2 C9 N1 . . 123.6(3) ?
C10 C13 H13A . . 109.5 ?
C10 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C10 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C9 N3 H3A . . 120.0 ?
C9 N3 H3B . . 120.0 ?
H3A N3 H3B . . 120.0 ?
N4 C15 N6 . . 117.9(3) ?
N4 C15 N5 . . 125.0(3) ?
N6 C15 N5 . . 117.2(3) ?
N5 C16 C17 . . 121.7(3) ?
N5 C16 C20 . . 115.9(4) ?
C17 C16 C20 . . 122.4(4) ?
C16 C17 C18 . . 118.3(4) ?
C16 C17 H17 . . 120.8 ?
C18 C17 H17 . . 120.8 ?
N4 C18 C17 . . 121.3(4) ?
N4 C18 C19 . . 117.4(3) ?
C17 C18 C19 . . 121.3(4) ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C16 C20 H20A . . 109.5 ?
C16 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C16 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
C12 N1 C9 . . 117.1(3) ?
C12 N1 Cu1 . . 119.1(2) ?
C9 N1 Cu1 . . 123.0(2) ?
C12 C11 C10 . . 118.5(4) ?
C12 C11 H11 . . 120.8 ?
C10 C11 H11 . . 120.8 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C18 N4 C15 . . 117.3(3) ?
C16 N5 C15 . . 116.4(3) ?
C15 N6 H6A . . 120.0 ?
C15 N6 H6B . . 120.0 ?
H6A N6 H6B . . 120.0 ?
C7 O1 Cu1 . . 103.5(2) ?
C7 O2 Cu1 . . 77.0(2) ?
C8 O4 Cu1 . 4_566 128.1(2) ?
Cu1 O5 H5E . . 152(5) ?
Cu1 O5 H5F . . 115(4) ?
H5E O5 H5F . . 87(5) ?
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 O5 . 1.926(3) yes
Cu1 O1 . 1.950(2) yes
Cu1 O4 4_665 1.955(2) yes
Cu1 N1 . 2.011(3) yes
Cu1 O2 . 2.530(3) yes
C1 C6 . 1.391(5) ?
C1 C2 . 1.391(5) ?
C1 C7 . 1.497(5) ?
C2 C3 . 1.374(5) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.388(5) ?
C3 C8 . 1.501(5) ?
C4 C5 . 1.392(5) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.377(5) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 O2 . 1.258(4) ?
C7 O1 . 1.264(4) ?
C8 O3 . 1.251(5) ?
C8 O4 . 1.272(4) ?
C12 N1 . 1.350(4) ?
C12 C11 . 1.360(5) ?
C12 C14 . 1.496(5) ?
C10 N2 . 1.316(5) ?
C10 C11 . 1.405(5) ?
C10 C13 . 1.479(5) ?
N2 C9 . 1.338(5) ?
C9 N3 . 1.326(5) ?
C9 N1 . 1.366(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
N3 H3A . 0.8600 ?
N3 H3B . 0.8600 ?
C15 N4 . 1.334(5) ?
C15 N6 . 1.336(5) ?
C15 N5 . 1.363(4) ?
C16 N5 . 1.342(5) ?
C16 C17 . 1.361(5) ?
C16 C20 . 1.502(5) ?
C17 C18 . 1.390(5) ?
C17 H17 . 0.9300 ?
C18 N4 . 1.330(5) ?
C18 C19 . 1.501(6) ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 0.9600 ?
C11 H11 . 0.9300 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
N6 H6A . 0.8600 ?
N6 H6B . 0.8600 ?
O4 Cu1 4_566 1.955(2) ?
O5 H5E . 0.843(10) ?
O5 H5F . 0.846(10) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_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
N3 H3A N4 1_556 0.86 2.14 2.994(4) 174.5 yes
N6 H6A N2 1_554 0.86 2.25 3.109(4) 174.5 yes
N3 H3B O2 . 0.86 2.16 2.944(4) 152.4 yes
O5 H5E N5 3_756 0.843(10) 1.98(4) 2.712(4) 144(6) yes
O5 H5F O3 4_665 0.846(10) 1.76(3) 2.507(4) 145(5) yes
