#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/39/2013993.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_2013993
loop_
_publ_author_name
'A. van der Lee'
'M. Barboiu'
_publ_section_title
;A two-dimensional network of R_2^2(16) and
 R_4^2(8) rings in
 trans-bis(4-aminopyridine-κN¹)bis(benzoato-κ²O,O')copper(II)
 benzene 0.75-solvate
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m156
_journal_page_last               m158
_journal_paper_doi               10.1107/S0108270104003749
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          '[Cu (C7 H5 O2)2 (C5 H6 N2)2], 0.75C6 H6'
_chemical_formula_moiety         'C24 H22 Cu1 N4 O4, 0.75C6 H5'
_chemical_formula_sum            'C28.5 H26.5 Cu N4 O4'
_chemical_formula_weight         552.59
_chemical_name_systematic        ?
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 98.773(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0100(10)
_cell_length_b                   9.0360(8)
_cell_length_c                   20.450(2)
_cell_measurement_reflns_used    2367
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.56
_cell_measurement_theta_min      4.31
_cell_volume                     2741.2(4)
_computing_cell_refinement       'CrysAlisRED (Oxford Diffraction, 2002)'
_computing_data_collection       'CrysAlisCCD (Oxford Diffraction, 2002)'
_computing_data_reduction        CrysAlisRED
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'CRYSTALS (Watkin et al, 2001)'
_computing_structure_solution    'SIR92 (Altomare et al, 1994)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 17
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Xcalibur CCD'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.08
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            50463
_diffrn_reflns_theta_full        30.336
_diffrn_reflns_theta_max         32.272
_diffrn_reflns_theta_min         2.899
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  30
_diffrn_standards_number         '4 frames'
_exptl_absorpt_coefficient_mu    0.837
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
Schwarzenbach & Flack (1991)
;
_exptl_crystal_colour            ' translucent pale blue'
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ' prism '
_exptl_crystal_F_000             1146
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.51
_refine_diff_density_min         -0.61
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9487
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1725
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 %Tp=P(6)*max(F$_o^2$,0) + (1-P(6))F$_c^2$.
 \hfill\break
 Method = SHELXL 97 (Sheldrick, 1997).
 \hfill\hbreak
 W = 1.0 / [$σ ^2(F^*)+(P(1)p)^2+P(2)p+P(4)+P(5)\sin(θ)$].
 \hfill\break
 The P(1)-P(5) are
 0.0859, 0.00, 0.00, 0.00, 0.00, and 0.333 respectively.
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1679
_refine_ls_wR_factor_gt          0.1390
_refine_ls_wR_factor_ref         0.1390
_reflns_number_gt                1725
_reflns_number_total             4535
_reflns_threshold_expression     I>2u(I)
_cod_data_source_file            gd1293.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Gaussian' changed to
'gaussian' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C28.5 H26.5 Cu1 N4 O4'
_cod_database_code               2013993
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y,1/2-z
-x,-y,-z
x,-y,1/2+z
1/2+x,1/2+y,z
1/2-x,1/2+y,1/2-z
1/2-x,1/2-y,-z
1/2+x,1/2-y,1/2+z
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_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cu1 0.0000 0.0000 0.5000 0.0329 Uani S 1.0000 Cu
N2 -0.0622(3) -0.1926(5) 0.4992(2) 0.0327 Uani . 1.0000 N
C3 -0.1170(4) -0.2247(6) 0.5437(3) 0.0451 Uani . 1.0000 C
C4 -0.1617(4) -0.3556(6) 0.5451(3) 0.0500 Uani . 1.0000 C
C5 -0.1509(4) -0.4654(6) 0.4993(3) 0.0404 Uani . 1.0000 C
N6 -0.1920(4) -0.5982(5) 0.4998(3) 0.0674 Uani . 1.0000 N
C7 -0.0931(4) -0.4328(6) 0.4538(3) 0.0371 Uani . 1.0000 C
C8 -0.0531(4) -0.2978(6) 0.4547(3) 0.0339 Uani . 1.0000 C
O9 0.0323(2) -0.0093(4) 0.59658(15) 0.0328 Uani . 1.0000 O
C10 0.1081(4) -0.0739(6) 0.6100(3) 0.0345 Uani . 1.0000 C
O11 0.1492(3) -0.1286(4) 0.56737(19) 0.0459 Uani . 1.0000 O
C12 0.1479(4) -0.0795(7) 0.6811(3) 0.0382 Uani . 1.0000 C
C13 0.2260(6) -0.1492(12) 0.7029(4) 0.1050 Uani . 1.0000 C
C14 0.2638(7) -0.1490(14) 0.7705(4) 0.1318 Uani . 1.0000 C
C15 0.2209(5) -0.0858(11) 0.8146(3) 0.0791 Uani . 1.0000 C
C16 0.1458(5) -0.0094(12) 0.7949(3) 0.0839 Uani . 1.0000 C
C17 0.1085(4) -0.0035(9) 0.7279(3) 0.0627 Uani . 1.0000 C
H26 -0.1112 -0.1552 0.5859 0.0500 Uiso R 1.0000 H
H27 -0.2034 -0.3770 0.5789 0.0500 Uiso R 1.0000 H
H30 -0.2310 -0.6185 0.5321 0.0500 Uiso R 1.0000 H
H29 -0.0140 -0.2678 0.4157 0.0500 Uiso R 1.0000 H
H28 -0.0866 -0.5072 0.4158 0.0500 Uiso R 1.0000 H
C18 0.4804(3) 0.1525(13) 0.21740(19) 0.130(3) Uiso D 0.7500 C
C19 0.4601(4) 0.0226(12) 0.1854(2) 0.130(3) Uiso D 0.7500 C
C20 0.4802(4) -0.1104(13) 0.2183(2) 0.130(3) Uiso D 0.7500 C
H32 0.4660 0.2498 0.19346 0.0500 Uiso R 0.7500 H
H34 0.4644 -0.2066 0.1946 0.0500 Uiso R 0.7500 H
H33 0.4293 0.0228 0.1379 0.0500 Uiso R 0.7500 H
H25 0.2572 -0.2036 0.6702 0.0500 Uiso R 1.0000 H
H24 0.3235 -0.1972 0.7848 0.0500 Uiso R 1.0000 H
H23 0.2446 -0.0964 0.8628 0.0500 Uiso R 1.0000 H
H22 0.1163 0.0451 0.8284 0.0500 Uiso R 1.0000 H
H21 0.0531 0.0567 0.7136 0.0500 Uiso R 1.0000 H
H31 -0.1815 -0.6737 0.4681 0.0500 Uiso R 1.0000 H
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_IV_Table_2.2B
'N   ' 0.0061 0.0033 International_Tables_Vol_IV_Table_2.2B
'H   ' 0.0000 0.0000 International_Tables_Vol_IV_Table_2.2B
'Cu  ' 0.2630 1.2660 International_Tables_Vol_IV_Table_2.2B
'Cl  ' 0.1484 0.1585 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 International_Tables_Vol_IV_Table_2.2B
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
O9 Cu1 O11 . . 53.91(13) no
O9 Cu1 N2 . . 90.83(16) no
O9 Cu1 O9 . 3_556 180.00 no
O9 Cu1 O11 . 3_556 126.09(13) no
O9 Cu1 N2 . 3_556 89.17(16) no
O11 Cu1 N2 . . 88.81(15) no
O9 Cu1 O11 3_556 . 126.09(13) no
O11 Cu1 O11 . 3_556 180.00 no
O11 Cu1 N2 . 3_556 91.19(15) no
O9 Cu1 N2 3_556 . 89.17(16) no
O11 Cu1 N2 3_556 . 91.19(15) no
N2 Cu1 N2 . 3_556 180.00 no
O9 Cu1 O11 3_556 3_556 53.91(13) no
O9 Cu1 N2 3_556 3_556 90.83(16) no
O11 Cu1 N2 3_556 3_556 88.81(15) no
Cu1 O9 C10 . . 108.2(3) no
Cu1 O11 C10 . . 74.1(3) no
Cu1 N2 C3 . . 121.4(4) no
Cu1 N2 C8 . . 122.4(4) no
C3 N2 C8 . . 116.3(5) no
C5 N6 H30 . . 119.99 no
C5 N6 H31 . . 119.93 no
H30 N6 H31 . . 120.07 no
N2 C3 C4 . . 123.7(5) no
C3 C4 C5 . . 119.8(6) no
N6 C5 C4 . . 121.9(6) no
C4 C5 C7 . . 116.5(5) no
N6 C5 C7 . . 121.6(5) no
C5 C7 C8 . . 119.9(5) no
N2 C8 C7 . . 123.8(6) no
O9 C10 O11 . . 123.7(5) no
O9 C10 C12 . . 116.1(5) no
O11 C10 C12 . . 120.2(5) no
C10 C12 C13 . . 122.7(6) no
C10 C12 C17 . . 120.7(5) no
C13 C12 C17 . . 116.5(6) no
C12 C13 C14 . . 121.6(8) no
C13 C14 C15 . . 120.4(9) no
C14 C15 C16 . . 119.9(7) no
C15 C16 C17 . . 120.7(7) no
C12 C17 C16 . . 120.6(7) no
N2 C3 H26 . . 116.06 no
C4 C3 H26 . . 118.48 no
C3 C4 H27 . . 122.30 no
C5 C4 H27 . . 117.91 no
C5 C7 H28 . . 119.89 no
C8 C7 H28 . . 119.83 no
N2 C8 H29 . . 116.22 no
C7 C8 H29 . . 119.85 no
C12 C13 H25 . . 118.74 no
C14 C13 H25 . . 119.68 no
C13 C14 H24 . . 119.64 no
C15 C14 H24 . . 119.96 no
C14 C15 H23 . . 119.75 no
C16 C15 H23 . . 120.37 no
C15 C16 H22 . . 119.41 no
C17 C16 H22 . . 119.93 no
C12 C17 H21 . . 119.52 no
C16 C17 H21 . . 119.86 no
C18 C18 C19 2_655 . 120.0(9) no
C18 C19 C20 . . 120.0(5) no
C19 C20 C20 . 2_655 120.0(10) no
C19 C18 H32 . . 120.15 no
C18 C18 H32 2_655 . 119.83 no
C18 C19 H33 . . 119.92 no
C20 C19 H33 . . 120.10 no
C19 C20 H34 . . 119.80 no
C20 C20 H34 2_655 . 120.19 no
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 O9 . . 1.962(3) yes
Cu1 O11 . . 2.706(4) yes
Cu1 N2 . . 1.974(5) yes
Cu1 O9 . 3_556 1.962(3) yes
Cu1 O11 . 3_556 2.706(4) yes
Cu1 N2 . 3_556 1.974(5) yes
O9 C10 . . 1.271(7) yes
O11 C10 . . 1.245(7) yes
N2 C3 . . 1.348(7) no
N2 C8 . . 1.337(7) no
N6 C5 . . 1.350(7) no
N6 H30 . . 0.96 no
N6 H31 . . 0.97 no
C3 C4 . . 1.362(8) no
C4 C5 . . 1.391(8) no
C5 C7 . . 1.397(9) no
C7 C8 . . 1.359(8) no
C10 C12 . . 1.486(9) no
C12 C17 . . 1.382(9) no
C12 C13 . . 1.345(11) no
C13 C14 . . 1.412(12) no
C14 C15 . . 1.316(12) no
C15 C16 . . 1.331(12) no
C16 C17 . . 1.400(9) no
C3 H26 . . 1.06 no
C4 H27 . . 1.02 no
C7 H28 . . 1.04 no
C8 H29 . . 1.09 no
C13 H25 . . 1.00 no
C14 H24 . . 1.00 no
C15 H23 . . 1.00 no
C16 H22 . . 1.00 no
C17 H21 . . 1.00 no
C18 C19 . . 1.356(14) no
C18 C18 . 2_655 1.373(6) no
C19 C20 . . 1.388(14) no
C20 C20 . 2_655 1.341(6) no
C18 H32 . . 1.01 no
C19 H33 . . 1.01 no
C20 H34 . . 1.01 no
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
N6 H30 O11 5_445 0.96 2.04 2.945(7) 156 yes
N6 H31 O11 3_546 0.97 2.01 2.943(6) 159 yes
C3 H26 O9 . 1.06 2.51 3.040(7) 110 yes
C8 H29 O9 3_556 1.09 2.53 3.000(7) 105 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O11 Cu1 O9 C10 . . . 2.0(3) no
N2 Cu1 O9 C10 . . . 89.9(4) no
O11 Cu1 O9 C10 3_556 . . -178.0(3) no
N2 Cu1 O9 C10 3_556 . . -90.1(4) no
O9 Cu1 O11 C10 . . . -2.0(3) no
N2 Cu1 O11 C10 . . . -93.9(3) no
O9 Cu1 O11 C10 3_556 . . 178.0(3) no
N2 Cu1 O11 C10 3_556 . . 86.1(3) no
O9 Cu1 N2 C3 . . . 44.0(4) no
O9 Cu1 N2 C8 . . . -136.4(4) no
O11 Cu1 N2 C3 . . . 97.9(4) no
O11 Cu1 N2 C8 . . . -82.5(4) no
O9 Cu1 N2 C3 3_556 . . -136.0(4) no
O9 Cu1 N2 C8 3_556 . . 43.6(4) no
O11 Cu1 N2 C3 3_556 . . -82.1(4) no
O11 Cu1 N2 C8 3_556 . . 97.5(4) no
Cu1 O9 C10 O11 . . . -4.3(7) no
Cu1 O9 C10 C12 . . . 174.7(4) no
Cu1 O11 C10 O9 . . . 3.1(5) no
Cu1 O11 C10 C12 . . . -175.9(6) no
C8 N2 C3 C4 . . . 0.1(8) no
Cu1 N2 C8 C7 . . . 178.3(5) no
Cu1 N2 C3 C4 . . . 179.7(5) no
C3 N2 C8 C7 . . . -2.1(8) no
N2 C3 C4 C5 . . . 0.8(9) no
C3 C4 C5 N6 . . . 178.3(6) no
C3 C4 C5 C7 . . . 0.1(9) no
C4 C5 C7 C8 . . . -2.0(9) no
N6 C5 C7 C8 . . . 179.9(6) no
C5 C7 C8 N2 . . . 3.1(9) no
O9 C10 C12 C13 . . . 177.4(7) no
O9 C10 C12 C17 . . . -7.1(9) no
O11 C10 C12 C13 . . . -3.7(10) no
O11 C10 C12 C17 . . . 171.9(6) no
C17 C12 C13 C14 . . . 2.3(13) no
C10 C12 C17 C16 . . . 179.7(7) no
C13 C12 C17 C16 . . . -4.5(11) no
C10 C12 C13 C14 . . . 178.0(8) no
C12 C13 C14 C15 . . . 3.2(17) no
C13 C14 C15 C16 . . . -6.5(17) no
C14 C15 C16 C17 . . . 4.2(15) no
C15 C16 C17 C12 . . . 1.4(13) no
C18 C18 C19 C20 2_655 . . -1.0(8) no
C19 C18 C18 C19 . 2_655 2_655 1.5(7) no
C18 C19 C20 C20 . . 2_655 -0.1(9) no
C19 C20 C20 C19 . 2_655 2_655 0.6(9) no
