#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/96/2239639.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_2239639
loop_
_publ_author_name
'Geiger, David K.'
'Parsons, Dylan E.'
_publ_section_title
;
 Poly[[tris(μ₂-acetato-κ²O:O')(4-chlorobenzene-1,2-diamine-κN)(μ₃-hydroxido)dizinc]
 ethanol monosolvate]
;
_journal_coeditor_code           GG2136
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m247
_journal_page_last               m248
_journal_paper_doi               10.1107/S1600536814012641
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac
'[Zn2 (C2 H3 O2)3 (O H) (C6 H7 Cl N2)], C2 H6 O'
_chemical_formula_moiety         'C12 H17 Cl N2 O7 Zn2, C2 H6 O'
_chemical_formula_sum            'C14 H23 Cl N2 O8 Zn2'
_chemical_formula_weight         513.53
_chemical_name_systematic
'Poly[[tris(μ₂-acetato-κ²O:O')(4-chlorobenzene-1,2-diamine-κN)(μ₃-hydroxido)dizinc] ethanol monosolvate]'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                101.511(6)
_cell_angle_beta                 96.399(6)
_cell_angle_gamma                109.817(5)
_cell_formula_units_Z            2
_cell_length_a                   8.0769(12)
_cell_length_b                   10.8723(19)
_cell_length_c                   12.909(3)
_cell_measurement_reflns_used    2325
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.8734
_cell_measurement_theta_min      2.2807
_cell_volume                     1025.1(3)
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'SAINT (Bruker, 2013)'
_computing_molecular_graphics
'PLATON (Spek, 2009) and Mercury (Macrae et al., 2008)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 8.3330
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'Bruker SMART X2S benchtop'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'doubly curved silicon crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0611
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6443
_diffrn_reflns_theta_full        25.11
_diffrn_reflns_theta_max         25.11
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    2.511
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2013)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.976
_refine_diff_density_min         -1.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     92
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0588
_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)+(0.0797P)²+5.5001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1813
_reflns_number_gt                2403
_reflns_number_total             3329
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2136sup1.cif
_cod_data_source_block           I
_cod_database_code               2239639
_cod_database_fobs_code          2239639
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn Zn1 0.51291(11) 0.64882(9) 0.49816(7) 0.0220(3) Uani d 1 . .
Zn Zn2 0.10138(11) 0.36887(9) 0.47758(7) 0.0235(3) Uani d 1 . .
O O1 0.3290(7) 0.4519(5) 0.4368(4) 0.0206(12) Uani d 1 . .
H H1 0.311(11) 0.419(8) 0.370(2) 0.031 Uiso d 1 . .
Cl Cl1 0.1090(8) 0.5949(6) 0.0220(4) 0.0601(15) Uani d 0.5 . .
Cl Cl2 0.4363(11) 0.9055(7) 0.0139(4) 0.087(2) Uani d 0.5 . .
N N1 0.6409(9) 0.9892(7) 0.4111(6) 0.0293(16) Uani d 1 . .
H H1A 0.744(6) 1.047(7) 0.399(6) 0.035 Uiso d 1 . .
H H1B 0.682(9) 0.964(8) 0.469(4) 0.035 Uiso d 1 . .
N N2 0.3623(9) 0.7554(7) 0.4280(5) 0.0247(15) Uani d 1 . .
H H2A 0.242(3) 0.719(7) 0.422(6) 0.03 Uiso d 1 . .
H H2B 0.396(9) 0.822(6) 0.490(4) 0.03 Uiso d 1 . .
C C1 0.5200(11) 0.8997(8) 0.3188(7) 0.0273(17) Uani d 1 . .
C C2 0.3789(11) 0.7860(8) 0.3266(6) 0.0232(16) Uani d 1 . .
C C3 0.2564(12) 0.6995(9) 0.2341(7) 0.0340(19) Uani d 1 . .
H H3 0.1629 0.6209 0.2395 0.041 Uiso calc 1 . .
C C4 0.2699(14) 0.7271(11) 0.1347(8) 0.050(2) Uani d 1 . .
H H4 0.1854 0.6683 0.0721 0.06 Uiso calc 0.5 . .
C C5 0.4063(15) 0.8402(12) 0.1269(8) 0.051(2) Uani d 1 . .
H H5 0.4145 0.8598 0.0588 0.062 Uiso calc 0.5 . .
C C6 0.5331(14) 0.9267(10) 0.2183(8) 0.045(2) Uani d 1 . .
H H6 0.628 1.0037 0.2117 0.054 Uiso calc 1 . .
O O71 0.0171(7) 0.1738(5) 0.3941(5) 0.0304(14) Uani d 1 . .
O O72 0.7122(7) 0.8392(5) 0.5729(5) 0.0334(14) Uani d 1 . .
C C7 0.1261(11) 0.1117(8) 0.3829(7) 0.030(2) Uani d 1 . .
C C71 0.0524(14) -0.0317(10) 0.3175(10) 0.062(4) Uani d 1 . .
H H71A 0.073 -0.0348 0.2438 0.093 Uiso calc 1 . .
H H71B -0.0767 -0.071 0.3161 0.093 Uiso calc 1 . .
H H71C 0.1127 -0.0834 0.3498 0.093 Uiso calc 1 . .
O O81 -0.1322(7) 0.3856(5) 0.4406(4) 0.0243(12) Uani d 1 . .
O O82 0.4119(7) 0.6770(6) 0.6442(4) 0.0260(13) Uani d 1 . .
C C8 -0.2514(11) 0.3399(7) 0.3538(6) 0.0213(17) Uani d 1 . .
C C81 -0.1933(12) 0.3104(9) 0.2482(6) 0.033(2) Uani d 1 . .
H H20A -0.2959 0.2829 0.189 0.05 Uiso calc 1 . .
H H20B -0.1474 0.2373 0.2451 0.05 Uiso calc 1 . .
H H20C -0.0986 0.3917 0.2416 0.05 Uiso calc 1 . .
O O91 0.1070(7) 0.3617(6) 0.6295(4) 0.0265(13) Uani d 1 . .
O O92 0.3883(8) 0.3702(6) 0.6454(5) 0.0360(15) Uani d 1 . .
C C9 0.2520(12) 0.3665(8) 0.6821(7) 0.0277(19) Uani d 1 . .
C C91 0.2600(14) 0.3703(10) 0.7993(7) 0.039(2) Uani d 1 . .
H H91A 0.355 0.3401 0.8245 0.059 Uiso calc 1 . .
H H91B 0.1445 0.3104 0.8094 0.059 Uiso calc 1 . .
H H91C 0.2858 0.4629 0.8406 0.059 Uiso calc 1 . .
O OE1 0.7175(15) 0.6924(13) 0.7773(8) 0.062(3) Uani d 0.7 A 1
H H1E1 0.6255 0.7008 0.7473 0.093 Uiso calc 0.7 A 1
C C1E1 0.711(4) 0.698(2) 0.8858(13) 0.103(9) Uani d 0.7 A 1
H HE1A 0.7271 0.6172 0.9035 0.124 Uiso calc 0.7 A 1
H HE1B 0.5934 0.6975 0.9 0.124 Uiso calc 0.7 A 1
C C2E1 0.855(4) 0.821(3) 0.954(2) 0.126(9) Uani d 0.7 A 1
H HE1C 0.9712 0.8238 0.9361 0.189 Uiso calc 0.7 A 1
H HE1D 0.8568 0.8222 1.0297 0.189 Uiso calc 0.7 A 1
H HE1E 0.8339 0.9008 0.94 0.189 Uiso calc 0.7 A 1
O OE2 0.719(4) 0.591(3) 0.7894(18) 0.062(3) Uani d 0.3 B 2
H H1E2 0.6074 0.5492 0.7742 0.093 Uiso calc 0.3 B 2
C C1E2 0.765(11) 0.688(4) 0.887(3) 0.103(9) Uani d 0.3 B 2
H HE2A 0.8724 0.6864 0.9316 0.124 Uiso calc 0.3 B 2
H HE2B 0.6656 0.6665 0.9267 0.124 Uiso calc 0.3 B 2
C C2E2 0.803(9) 0.821(4) 0.869(5) 0.126(9) Uani d 0.3 B 2
H HE2C 0.9333 0.8675 0.8779 0.189 Uiso calc 0.3 B 2
H HE2D 0.7577 0.8733 0.9218 0.189 Uiso calc 0.3 B 2
H HE2E 0.7449 0.813 0.7962 0.189 Uiso calc 0.3 B 2
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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'
Cl Cl 0.1484 0.1585 '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
O1 Zn1 O92 . 2_666 88.2(2)
O1 Zn1 O72 . . 173.5(2)
O92 Zn1 O72 2_666 . 94.2(3)
O1 Zn1 O82 . . 93.6(2)
O92 Zn1 O82 2_666 . 177.4(2)
O72 Zn1 O82 . . 84.2(2)
O1 Zn1 O1 . 2_666 82.3(2)
O92 Zn1 O1 2_666 2_666 91.3(2)
O72 Zn1 O1 . 2_666 91.6(2)
O82 Zn1 O1 . 2_666 90.8(2)
O1 Zn1 N2 . . 99.1(2)
O92 Zn1 N2 2_666 . 86.4(2)
O72 Zn1 N2 . . 87.1(2)
O82 Zn1 N2 . . 91.5(2)
O1 Zn1 N2 2_666 . 177.3(2)
O1 Zn2 O81 . . 130.8(2)
O1 Zn2 O91 . . 117.1(2)
O81 Zn2 O91 . . 101.1(2)
O1 Zn2 O71 . . 103.6(2)
O81 Zn2 O71 . . 94.7(2)
O91 Zn2 O71 . . 104.5(2)
Zn2 O1 Zn1 . . 127.8(2)
Zn2 O1 Zn1 . 2_666 101.7(2)
Zn1 O1 Zn1 . 2_666 97.7(2)
Zn2 O1 H1 . . 105.(6)
Zn1 O1 H1 . . 117.(6)
Zn1 O1 H1 2_666 . 103.(6)
C4 Cl1 Cl1 . 2_565 144.8(6)
C5 Cl2 Cl2 . 2_675 136.3(6)
C1 N1 H1A . . 115.(5)
C1 N1 H1B . . 125.(5)
H1A N1 H1B . . 102.(4)
C2 N2 Zn1 . . 122.9(5)
C2 N2 H2A . . 102.(5)
Zn1 N2 H2A . . 115.(6)
C2 N2 H2B . . 121.(6)
Zn1 N2 H2B . . 92.(5)
H2A N2 H2B . . 102.(4)
C6 C1 N1 . . 120.2(8)
C6 C1 C2 . . 119.1(8)
N1 C1 C2 . . 120.6(7)
C3 C2 C1 . . 120.0(8)
C3 C2 N2 . . 119.5(7)
C1 C2 N2 . . 120.5(7)
C4 C3 C2 . . 120.6(9)
C4 C3 H3 . . 119.7
C2 C3 H3 . . 119.7
C5 C4 C3 . . 119.7(9)
C5 C4 Cl1 . . 126.1(8)
C3 C4 Cl1 . . 114.0(8)
C5 C4 H4 . . 120.2
C3 C4 H4 . . 120.2
C4 C5 C6 . . 120.8(9)
C4 C5 Cl2 . . 127.8(9)
C6 C5 Cl2 . . 111.2(8)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C1 C6 C5 . . 119.9(9)
C1 C6 H6 . . 120.1
C5 C6 H6 . . 120.1
C7 O71 Zn2 . . 121.6(5)
C7 O72 Zn1 2_666 . 138.8(6)
O72 C7 O71 2_666 . 124.4(8)
O72 C7 C71 2_666 . 117.7(8)
O71 C7 C71 . . 117.8(7)
C7 C71 H71A . . 109.5
C7 C71 H71B . . 109.5
H71A C71 H71B . . 109.5
C7 C71 H71C . . 109.5
H71A C71 H71C . . 109.5
H71B C71 H71C . . 109.5
C8 O81 Zn2 . . 132.6(5)
C8 O82 Zn1 2_566 . 123.4(5)
O82 C8 O81 2_566 . 121.4(7)
O82 C8 C81 2_566 . 120.2(7)
O81 C8 C81 . . 118.4(7)
C8 C81 H20A . . 109.5
C8 C81 H20B . . 109.5
H20A C81 H20B . . 109.5
C8 C81 H20C . . 109.5
H20A C81 H20C . . 109.5
H20B C81 H20C . . 109.5
C9 O91 Zn2 . . 117.2(5)
C9 O92 Zn1 . 2_666 143.2(6)
O92 C9 O91 . . 125.6(8)
O92 C9 C91 . . 117.3(8)
O91 C9 C91 . . 117.1(8)
C9 C91 H91A . . 109.5
C9 C91 H91B . . 109.5
H91A C91 H91B . . 109.5
C9 C91 H91C . . 109.5
H91A C91 H91C . . 109.5
H91B C91 H91C . . 109.5
C1E1 OE1 H1E1 . . 109.5
OE1 C1E1 C2E1 . . 109.4(18)
OE1 C1E1 HE1A . . 109.8
C2E1 C1E1 HE1A . . 109.8
OE1 C1E1 HE1B . . 109.8
C2E1 C1E1 HE1B . . 109.8
HE1A C1E1 HE1B . . 108.2
C1E1 C2E1 HE1C . . 109.5
C1E1 C2E1 HE1D . . 109.5
HE1C C2E1 HE1D . . 109.5
C1E1 C2E1 HE1E . . 109.5
HE1C C2E1 HE1E . . 109.5
HE1D C2E1 HE1E . . 109.5
C1E2 OE2 H1E2 . . 109.5
OE2 C1E2 C2E2 . . 111.(3)
OE2 C1E2 HE2A . . 109.5
C2E2 C1E2 HE2A . . 109.5
OE2 C1E2 HE2B . . 109.5
C2E2 C1E2 HE2B . . 109.5
HE2A C1E2 HE2B . . 108.1
C1E2 C2E2 HE2C . . 109.5
C1E2 C2E2 HE2D . . 109.5
HE2C C2E2 HE2D . . 109.5
C1E2 C2E2 HE2E . . 109.5
HE2C C2E2 HE2E . . 109.5
HE2D C2E2 HE2E . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Zn1 O1 . 2.079(5)
Zn1 O92 2_666 2.098(6)
Zn1 O72 . 2.098(5)
Zn1 O82 . 2.143(5)
Zn1 O1 2_666 2.147(5)
Zn1 N2 . 2.185(7)
Zn2 O1 . 1.937(5)
Zn2 O81 . 1.971(5)
Zn2 O91 . 1.974(5)
Zn2 O71 . 2.017(5)
O1 Zn1 2_666 2.147(5)
O1 H1 . 0.84(2)
Cl1 C4 . 1.830(11)
Cl1 Cl1 2_565 2.128(12)
Cl2 C5 . 1.752(11)
Cl2 Cl2 2_675 2.086(14)
N1 C1 . 1.398(11)
N1 H1A . 0.91(2)
N1 H1B . 0.91(2)
N2 C2 . 1.423(10)
N2 H2A . 0.90(2)
N2 H2B . 0.90(2)
C1 C6 . 1.394(12)
C1 C2 . 1.400(11)
C2 C3 . 1.395(11)
C3 C4 . 1.383(13)
C3 H3 . 0.95
C4 C5 . 1.375(15)
C4 H4 . 0.95
C5 C6 . 1.399(14)
C5 H5 . 0.95
C6 H6 . 0.95
O71 C7 . 1.282(10)
O72 C7 2_666 1.248(10)
C7 O72 2_666 1.248(10)
C7 C71 . 1.494(12)
C71 H71A . 0.98
C71 H71B . 0.98
C71 H71C . 0.98
O81 C8 . 1.281(9)
O82 C8 2_566 1.251(9)
C8 O82 2_566 1.251(9)
C8 C81 . 1.500(11)
C81 H20A . 0.98
C81 H20B . 0.98
C81 H20C . 0.98
O91 C9 . 1.266(10)
O92 C9 . 1.237(10)
O92 Zn1 2_666 2.098(6)
C9 C91 . 1.499(12)
C91 H91A . 0.98
C91 H91B . 0.98
C91 H91C . 0.98
OE1 C1E1 . 1.398(15)
OE1 H1E1 . 0.84
C1E1 C2E1 . 1.474(17)
C1E1 HE1A . 0.99
C1E1 HE1B . 0.99
C2E1 HE1C . 0.98
C2E1 HE1D . 0.98
C2E1 HE1E . 0.98
OE2 C1E2 . 1.39(2)
OE2 H1E2 . 0.84
C1E2 C2E2 . 1.45(3)
C1E2 HE2A . 0.99
C1E2 HE2B . 0.99
C2E2 HE2C . 0.98
C2E2 HE2D . 0.98
C2E2 HE2E . 0.98
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
O1 H1 OE1 2_666 0.84(2) 1.99(3) 2.807(11) 166(8) y
O1 H1 OE2 2_666 0.84(2) 2.03(4) 2.83(2) 160(8) y
N2 H2A O81 2_566 0.90(2) 2.38(7) 2.914(9) 118(6) y
N2 H2B N1 2_676 0.91(6) 2.32(5) 3.128(10) 148(7) y
N1 H1A O71 1_665 0.91(7) 2.19(3) 3.082(9) 169(6) y
N1 H1B O72 . 0.91(6) 2.14(7) 3.013(9) 160(7) ?
OE1 H1E1 O82 . 0.84 1.97 2.780(11) 163 y
OE2 H1E2 O92 . 0.84 2.32 3.02(3) 140 y
