#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:31:49 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179635 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/99/4509947.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_4509947
loop_
_publ_author_name
'El Bakkali, H.'
'Castiñeiras, A.'
'García-Santos, I.'
'González-Pérez, J. M.'
'Niclós-Gutiérrez, J.'
_publ_section_title
;
 Metallo-Supramolecular Structures by Self-Assembly through Weak
 Interactions in Mixed Ligand Metal Complexes of Adenine and Malonate
;
_journal_issue                   1
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              249
_journal_paper_doi               10.1021/cg401455c
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C16 H18 N10 O10 Zn2, 2(H2 O)'
_chemical_formula_sum            'C16 H22 N10 O12 Zn2'
_chemical_formula_weight         677.17
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.121(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0521(3)
_cell_length_b                   10.5050(3)
_cell_length_c                   16.0669(6)
_cell_measurement_reflns_used    1866
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.89
_cell_volume                     1190.27(8)
_computing_cell_refinement       'APEX2 Software (Bruker, 2010)'
_computing_data_collection       'APEX2 Software (Bruker, 2010)'
_computing_data_reduction        'APEX2 Software (Bruker, 2010)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker X8 KappaAPEXII'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            38925
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.546
_diffrn_reflns_theta_min         2.316
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.889
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.067
_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     202
_refine_ls_number_reflns         3633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0224
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0200P)²+0.8595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0511
_refine_ls_wR_factor_ref         0.0525
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3185
_reflns_number_total             3633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg401455c_si_004.cif
_cod_data_source_block           07jnac401
_cod_database_code               4509947
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.527
_shelx_estimated_absorpt_t_max   0.772
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Zn1 Zn 0.01944(2) 0.05372(2) 0.41012(2) 0.00820(5) Uani 1 1 d . .
O1 O -0.15160(15) 0.16127(10) 0.33247(6) 0.01241(19) Uani 1 1 d . .
H1A H -0.181(2) 0.1368(17) 0.2869(12) 0.015 Uiso 1 1 d . U
H1B H -0.239(3) 0.1720(18) 0.3595(11) 0.015 Uiso 1 1 d . U
O11 O -0.19521(13) 0.03836(9) 0.50456(6) 0.00989(18) Uani 1 1 d . .
O12 O -0.39054(14) 0.19336(9) 0.46719(6) 0.01357(19) Uani 1 1 d . .
O21 O 0.22819(14) 0.04181(9) 0.32388(6) 0.01180(18) Uani 1 1 d . .
O22 O 0.44274(15) -0.06719(10) 0.25389(6) 0.0183(2) Uani 1 1 d . .
N1 N 0.21228(16) 0.43904(11) 0.47024(7) 0.0118(2) Uani 1 1 d . .
N3 N 0.10175(16) 0.22224(11) 0.47575(7) 0.0101(2) Uani 1 1 d . .
N7 N 0.18096(16) 0.31008(11) 0.68438(7) 0.0108(2) Uani 1 1 d . .
H7A H 0.205(2) 0.3602(16) 0.7278(11) 0.013 Uiso 1 1 d . U
N9 N -0.07976(15) -0.13623(10) 0.38275(7) 0.0097(2) Uani 1 1 d . .
N10 N 0.29799(18) 0.55412(11) 0.58740(8) 0.0137(2) Uani 1 1 d . .
H10A H 0.331(2) 0.6145(19) 0.5556(11) 0.016 Uiso 1 1 d . U
H10B H 0.327(3) 0.5574(17) 0.6380(12) 0.016 Uiso 1 1 d . U
C2 C 0.15008(19) 0.32959(13) 0.43752(8) 0.0121(2) Uani 1 1 d . .
H2 H 0.1389 0.3284 0.3786 0.015 Uiso 1 1 d R U
C4 C 0.11970(18) 0.23022(12) 0.55983(8) 0.0090(2) Uani 1 1 d . .
C5 C 0.18223(18) 0.33842(12) 0.60047(8) 0.0092(2) Uani 1 1 d . .
C6 C 0.23336(18) 0.44695(12) 0.55385(8) 0.0103(2) Uani 1 1 d . .
C8 C -0.11842(19) -0.18955(13) 0.30976(8) 0.0113(2) Uani 1 1 d . .
H8 H -0.1034 -0.1465 0.2582 0.014 Uiso 1 1 d R U
C11 C -0.32762(18) 0.11812(12) 0.52022(8) 0.0095(2) Uani 1 1 d . .
C12 C -0.4199(2) 0.12113(14) 0.60538(8) 0.0146(3) Uani 1 1 d . .
H12A H -0.5551 0.0997 0.5962 0.018 Uiso 1 1 d R U
H12B H -0.4170 0.2112 0.6235 0.018 Uiso 1 1 d R U
C21 C 0.35685(18) -0.04328(12) 0.31967(8) 0.0104(2) Uani 1 1 d . .
O2 O 0.72660(18) 0.07532(12) 0.18196(7) 0.0239(3) Uani 1 1 d . .
H2A H 0.636(3) 0.038(2) 0.1982(13) 0.029 Uiso 1 1 d . U
H2B H 0.746(3) 0.0501(19) 0.1359(14) 0.029 Uiso 1 1 d . U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Zn Zn 0.2839 1.4301 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
O21 Zn1 O1 92.57(4) . . y
O21 Zn1 O11 89.38(4) . 3_556 y
O1 Zn1 O11 174.32(4) . 3_556 y
O21 Zn1 N3 101.02(4) . . y
O1 Zn1 N3 90.15(4) . . y
O11 Zn1 N3 84.24(4) 3_556 . y
O21 Zn1 O11 171.96(4) . . y
O1 Zn1 O11 93.22(4) . . y
O11 Zn1 O11 85.39(4) 3_556 . y
N3 Zn1 O11 84.55(4) . . y
O21 Zn1 N9 92.25(4) . . y
O1 Zn1 N9 101.16(4) . . y
O11 Zn1 N9 84.09(4) 3_556 . y
N3 Zn1 N9 162.20(4) . . y
O11 Zn1 N9 81.15(4) . . y
O21 Zn1 Zn1 132.61(3) . 3_556 ?
O1 Zn1 Zn1 134.82(3) . 3_556 ?
O11 Zn1 Zn1 43.54(3) 3_556 3_556 ?
N3 Zn1 Zn1 82.37(3) . 3_556 ?
O11 Zn1 Zn1 41.86(2) . 3_556 ?
N9 Zn1 Zn1 79.91(3) . 3_556 ?
Zn1 O1 H1A 121.7(13) . . ?
Zn1 O1 H1B 102.0(14) . . ?
H1A O1 H1B 110.9(18) . . ?
C11 O11 Zn1 127.42(8) . 3_556 ?
C11 O11 Zn1 127.17(8) . . ?
Zn1 O11 Zn1 94.61(4) 3_556 . y
C11 O11 O11 153.29(9) . 3_556 ?
Zn1 O11 O11 48.29(3) 3_556 3_556 ?
Zn1 O11 O11 46.32(3) . 3_556 ?
C21 O21 Zn1 126.66(8) . . ?
C2 N1 C6 118.55(11) . . ?
C2 N3 C4 112.56(11) . . ?
C2 N3 Zn1 122.94(9) . . ?
C4 N3 Zn1 124.42(9) . . ?
C8 N7 C5 105.93(11) 3_556 . ?
C8 N7 H7A 124.4(11) 3_556 . ?
C5 N7 H7A 129.5(11) . . ?
C8 N9 C4 104.29(11) . 3_556 ?
C8 N9 Zn1 129.47(9) . . ?
C4 N9 Zn1 126.24(8) 3_556 . ?
C6 N10 H10A 119.0(12) . . ?
C6 N10 H10B 120.7(12) . . ?
H10A N10 H10B 119.2(17) . . ?
N3 C2 N1 129.19(12) . . ?
N3 C2 H2 115.4 . . ?
N1 C2 H2 115.4 . . ?
N3 C4 N9 126.96(12) . 3_556 ?
N3 C4 C5 123.29(12) . . ?
N9 C4 C5 109.74(11) 3_556 . ?
N7 C5 C4 106.32(11) . . ?
N7 C5 C6 133.99(12) . . ?
C4 C5 C6 119.68(12) . . ?
N10 C6 N1 119.44(12) . . ?
N10 C6 C5 123.85(12) . . ?
N1 C6 C5 116.71(12) . . ?
N9 C8 N7 113.73(12) . 3_556 ?
N9 C8 H8 123.1 . . ?
N7 C8 H8 123.1 3_556 . ?
O12 C11 O11 122.74(12) . . ?
O12 C11 C12 116.86(12) . . ?
O11 C11 C12 120.38(11) . . ?
C11 C12 C21 125.27(11) . 3_556 ?
C11 C12 H12A 106.0 . . ?
C21 C12 H12A 106.0 3_556 . ?
C11 C12 H12B 106.0 . . ?
C21 C12 H12B 106.0 3_556 . ?
H12A C12 H12B 106.3 . . ?
O22 C21 O21 122.27(12) . . ?
O22 C21 C12 114.93(12) . 3_556 ?
O21 C21 C12 122.78(12) . 3_556 ?
H2A O2 H2B 106(2) . . ?
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
Zn1 O21 2.0276(10) . y
Zn1 O1 2.0692(10) . y
Zn1 O11 2.0842(9) 3_556 y
Zn1 N3 2.1401(11) . y
Zn1 O11 2.1516(9) . y
Zn1 N9 2.1594(11) . y
Zn1 Zn1 3.1135(3) 3_556 y
O1 H1A 0.804(19) . ?
O1 H1B 0.761(19) . ?
O11 C11 1.2799(15) . ?
O11 Zn1 2.0842(9) 3_556 y
O11 O11 2.8729(18) 3_556 y
O12 C11 1.2434(16) . ?
O21 C21 1.2756(16) . ?
O22 C21 1.2448(16) . ?
N1 C2 1.3379(17) . ?
N1 C6 1.3537(17) . ?
N3 C2 1.3289(17) . ?
N3 C4 1.3592(16) . ?
N7 C8 1.3442(17) 3_556 ?
N7 C5 1.3807(16) . ?
N7 H7A 0.889(18) . ?
N9 C8 1.3275(17) . ?
N9 C4 1.3807(16) 3_556 ?
N10 C6 1.3285(17) . ?
N10 H10A 0.85(2) . ?
N10 H10B 0.838(19) . ?
C2 H2 0.9500 . ?
C4 N9 1.3806(16) 3_556 ?
C4 C5 1.3826(18) . ?
C5 C6 1.4114(18) . ?
C8 N7 1.3442(17) 3_556 ?
C8 H8 0.9500 . ?
C11 C12 1.5168(18) . ?
C12 C21 1.5214(18) 3_556 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C21 C12 1.5215(18) 3_556 ?
O2 H2A 0.79(2) . ?
O2 H2B 0.80(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O2 0.804(19) 1.917(19) 2.7188(15) 175.1(18) 1_455
O1 H1B O12 0.761(19) 2.049(19) 2.7665(14) 157.1(18) .
N7 H7A O21 0.889(18) 1.863(18) 2.7482(15) 173.2(16) 4_566
N10 H10A O12 0.85(2) 2.09(2) 2.8695(15) 152.0(17) 3_566
N10 H10B O22 0.838(19) 2.04(2) 2.8643(16) 170.3(18) 4_566
C12 H12A N9 0.99 2.63 3.5374(18) 153.1 3_456
C12 H12B O2 0.99 2.63 3.570(2) 157.9 4_466
O2 H2A O22 0.79(2) 1.97(2) 2.7558(17) 170(2) .
O2 H2B N1 0.80(2) 2.09(2) 2.8670(16) 165(2) 2_645
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C4 N3 C2 N1 0.4(2) . .
Zn1 N3 C2 N1 -176.56(11) . .
C6 N1 C2 N3 0.6(2) . .
C2 N3 C4 N9 179.45(12) . 3_556
Zn1 N3 C4 N9 -3.65(18) . 3_556
C2 N3 C4 C5 -0.24(18) . .
Zn1 N3 C4 C5 176.66(10) . .
C8 N7 C5 C4 -0.31(14) 3_556 .
C8 N7 C5 C6 -179.42(14) 3_556 .
N3 C4 C5 N7 179.87(12) . .
N9 C4 C5 N7 0.13(14) 3_556 .
N3 C4 C5 C6 -0.9(2) . .
N9 C4 C5 C6 179.39(11) 3_556 .
C2 N1 C6 N10 178.87(12) . .
C2 N1 C6 C5 -1.69(18) . .
N7 C5 C6 N10 0.3(2) . .
C4 C5 C6 N10 -178.76(13) . .
N7 C5 C6 N1 -179.15(14) . .
C4 C5 C6 N1 1.83(19) . .
C4 N9 C8 N7 0.32(15) 3_556 3_556
Zn1 N9 C8 N7 -178.93(9) . 3_556
Zn1 O11 C11 O12 160.06(9) 3_556 .
Zn1 O11 C11 O12 25.07(18) . .
O11 O11 C11 O12 90.1(2) 3_556 .
Zn1 O11 C11 C12 -22.05(17) 3_556 .
Zn1 O11 C11 C12 -157.04(9) . .
O11 O11 C11 C12 -92.0(2) 3_556 .
O12 C11 C12 C21 -176.00(13) . 3_556
O11 C11 C12 C21 6.0(2) . 3_556
Zn1 O21 C21 O22 158.04(10) . .
Zn1 O21 C21 C12 -23.28(18) . 3_556
