#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512704.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_4512704
loop_
_publ_author_name
'Hill, Matthew D.'
'El-Hankari, Samir'
'Chiacchia, Mauro'
'Tizzard, Graham J.'
'Coles, Simon J.'
'Bradshaw, Darren'
'Kitchen, Jonathan A.'
'Keene, Tony D.'
_publ_section_title
;
 Additive Effects in the Formation of Fluorescent Zinc Metal--Organic
 Frameworks with 5-Hydroxyisophthalate
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1452
_journal_paper_doi               10.1021/cg501808y
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C18 H14 N O11 Zn2'
_chemical_formula_sum            'C18 H14 N O11 Zn2'
_chemical_formula_weight         551.04
_chemical_melting_point          ?
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 115.424(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.6519(17)
_cell_length_b                   13.0546(9)
_cell_length_c                   26.4620(19)
_cell_measurement_reflns_used    36901
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.8
_cell_volume                     7379.3(9)
_computing_cell_refinement
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_collection
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_data_reduction
;
CrystalClear-SM Expert 3.1 b27 (Rigaku, 20112)
;
_computing_molecular_graphics    'DIAMOND 3.2g'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1243
_diffrn_reflns_av_unetI/netI     0.1353
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            24836
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.765
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    1.335
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.727
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    0.992
_exptl_crystal_description       Block
_exptl_crystal_F_000             2216
_exptl_crystal_size_max          0.040
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.694
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         6453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1628
_refine_ls_R_factor_gt           0.0993
_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)+(0.1275P)²+100.9881P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2577
_refine_ls_wR_factor_ref         0.2899
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3671
_reflns_number_total             6453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501808y_si_001.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'N/A' was changed to '?' - the value
is undefined or not given.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4512701--4512704.cif.
;
_cod_database_code               4512704
#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   0.949
_shelx_estimated_absorpt_t_max   0.987
_shelxl_version_number           2013-4
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O21A O 0.0068(9) 0.594(2) 0.1863(11) 0.111(6) Uani 0.5 1 d . . P A 1
C21A C 0.0684(7) 0.6199(16) 0.2026(8) 0.073(6) Uani 0.5 1 d G . P A 1
C22A C 0.1116(9) 0.5714(14) 0.2503(8) 0.062(6) Uani 0.5 1 d G . P A 1
H22A H 0.0979 0.5217 0.2689 0.075 Uiso 0.5 1 calc R U P A 1
C24A C 0.1748(8) 0.596(2) 0.2709(11) 0.048(7) Uani 0.5 1 d G . P A 1
C26A C 0.1948(8) 0.668(3) 0.2437(16) 0.050(4) Uani 0.5 1 d G . P A 1
H26A H 0.2380 0.6848 0.2578 0.060 Uiso 0.5 1 calc R U P A 1
C25A C 0.1515(12) 0.717(2) 0.1960(14) 0.076(8) Uani 0.5 1 d G . P A 1
C23A C 0.0883(11) 0.6926(17) 0.1755(8) 0.075(8) Uani 0.5 1 d G . P A 1
H23A H 0.0588 0.7257 0.1429 0.091 Uiso 0.5 1 calc R U P A 1
O21B O 0.0201(9) 0.712(2) 0.2329(11) 0.111(6) Uani 0.5 1 d . . P A 2
C21B C 0.0761(8) 0.6948(16) 0.2373(8) 0.073(6) Uani 0.5 1 d G . P A 2
C22B C 0.1215(9) 0.6324(14) 0.2763(8) 0.062(6) Uani 0.5 1 d G . P A 2
H22B H 0.1121 0.5940 0.3022 0.075 Uiso 0.5 1 calc R U P A 2
C24B C 0.1808(8) 0.626(2) 0.2775(12) 0.048(7) Uani 0.5 1 d G . P A 2
C26B C 0.1946(9) 0.682(3) 0.2397(16) 0.050(4) Uani 0.5 1 d G . P A 2
H26B H 0.2351 0.6783 0.2405 0.060 Uiso 0.5 1 calc R U P A 2
C25B C 0.1492(12) 0.745(2) 0.2006(13) 0.076(8) Uani 0.5 1 d G . P A 2
C23B C 0.0900(10) 0.7510(17) 0.1994(8) 0.075(8) Uani 0.5 1 d G . P A 2
H23B H 0.0589 0.7936 0.1727 0.091 Uiso 0.5 1 calc R U P A 2
C27 C 0.2250(6) 0.5488(10) 0.3185(5) 0.054(3) Uani 1 1 d . . . . .
C28 C 0.1705(5) 0.8079(11) 0.1678(4) 0.054(3) Uani 1 1 d . . . . .
N31 N 0.1434(17) 0.316(3) 0.1581(15) 0.268(15) Uiso 1 1 d . . . . .
H31A H 0.1820 0.3508 0.1612 0.321 Uiso 1 1 calc R U . . .
H31B H 0.1433 0.2439 0.1470 0.321 Uiso 1 1 calc R U . . .
C33 C 0.0811(18) 0.376(3) 0.1176(16) 0.239(17) Uiso 1 1 d . . . . .
H33A H 0.0785 0.3783 0.0796 0.358 Uiso 1 1 calc R U . . .
H33B H 0.0825 0.4465 0.1313 0.358 Uiso 1 1 calc R U . . .
H33C H 0.0443 0.3409 0.1171 0.358 Uiso 1 1 calc R U . . .
Zn1 Zn 0.25241(5) 0.36531(11) 0.38626(5) 0.0406(4) Uani 1 1 d . . . . .
Zn2 Zn 0.35934(5) 0.51385(10) 0.39631(5) 0.0392(4) Uani 1 1 d . . . . .
O11 O 0.3276(3) 0.4339(6) 0.4430(3) 0.044(2) Uani 1 1 d . . . . .
O14 O 0.5493(3) 0.4819(6) 0.5777(3) 0.047(2) Uani 1 1 d . . . . .
O12 O 0.2867(3) 0.2221(6) 0.5804(3) 0.051(2) Uani 1 1 d . . . . .
O25 O 0.2205(4) 0.7883(6) 0.1630(3) 0.052(2) Uani 1 1 d . . . . .
C18 C 0.5297(5) 0.4202(9) 0.6039(5) 0.044(3) Uani 1 1 d . . . . .
O15 O 0.5667(4) 0.3787(7) 0.6500(3) 0.067(3) Uani 1 1 d . . . . .
O1W O 0.3667(5) 0.6559(7) 0.4383(4) 0.071(3) Uani 1 1 d . . . . .
C15 C 0.4623(5) 0.3958(8) 0.5777(4) 0.038(3) Uani 1 1 d . . . . .
O23 O 0.2810(4) 0.5641(7) 0.3322(3) 0.060(2) Uani 1 1 d . . . . .
C17 C 0.3415(5) 0.2495(10) 0.6059(4) 0.051(3) Uani 1 1 d . . . . .
C11 C 0.3624(5) 0.4015(8) 0.4964(4) 0.039(3) Uani 1 1 d . . . . .
O13 O 0.3722(5) 0.2224(11) 0.6576(4) 0.118(5) Uani 1 1 d . . . . .
O24 O 0.1370(4) 0.8858(7) 0.1487(4) 0.066(3) Uani 1 1 d . . . . .
C16 C 0.4347(5) 0.3380(10) 0.6059(4) 0.052(3) Uani 1 1 d . . . . .
H16 H 0.4595 0.3169 0.6433 0.062 Uiso 1 1 calc R U . . .
C13 C 0.4261(4) 0.4257(8) 0.5241(4) 0.035(2) Uani 1 1 d . . . . .
H13 H 0.4448 0.4644 0.5049 0.042 Uiso 1 1 calc R U . . .
O22 O 0.2051(4) 0.4819(7) 0.3436(3) 0.058(2) Uani 1 1 d . . . . .
C12 C 0.3351(5) 0.3438(8) 0.5258(4) 0.039(3) Uani 1 1 d . . . . .
H12 H 0.2918 0.3273 0.5083 0.047 Uiso 1 1 calc R U . . .
C14 C 0.3721(5) 0.3114(10) 0.5802(4) 0.048(3) Uani 1 1 d . . . . .
C32 C 0.1318(17) 0.329(3) 0.2194(15) 0.232(16) Uiso 1 1 d . . . . .
H32A H 0.1665 0.2964 0.2508 0.349 Uiso 1 1 calc R U . . .
H32B H 0.0923 0.2963 0.2138 0.349 Uiso 1 1 calc R U . . .
H32C H 0.1302 0.4021 0.2277 0.349 Uiso 1 1 calc R U . . .
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'
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
O21A C21A C22A 116.3(17) . .
O21A C21A C23A 123.6(17) . .
C22A C21A C23A 120.0 . .
C21A C22A C24A 120.0 . .
C21A C22A H22A 120.0 . .
C24A C22A H22A 120.0 . .
C26A C24A C22A 120.0 . .
C26A C24A C27 113.9(16) . .
C22A C24A C27 126.0(16) . .
C24A C26A C25A 120.0 . .
C24A C26A H26A 120.0 . .
C25A C26A H26A 120.0 . .
C23A C25A C26A 120.0 . .
C23A C25A C28 117.8(17) . .
C26A C25A C28 121.9(18) . .
C25A C23A C21A 120.0 . .
C25A C23A H23A 120.0 . .
C21A C23A H23A 120.0 . .
C21B O21B O21B 143(3) . 2
O21B C21B C22B 127.0(17) . .
O21B C21B C23B 112.9(17) . .
C22B C21B C23B 120.0 . .
C21B C22B C24B 120.0 . .
C21B C22B H22B 120.0 . .
C24B C22B H22B 120.0 . .
C26B C24B C22B 120.0 . .
C26B C24B C27 124.2(17) . .
C22B C24B C27 115.6(16) . .
C24B C26B C25B 120.0 . .
C24B C26B H26B 120.0 . .
C25B C26B H26B 120.0 . .
C23B C25B C26B 120.0 . .
C23B C25B C28 124.4(17) . .
C26B C25B C28 115.2(18) . .
C25B C23B C21B 120.0 . .
C25B C23B H23B 120.0 . .
C21B C23B H23B 120.0 . .
O23 C27 O22 122.6(11) . .
O23 C27 C24A 124.4(13) . .
O22 C27 C24A 112.8(13) . .
O23 C27 C24B 115.1(13) . .
O22 C27 C24B 121.4(13) . .
O24 C28 O25 125.4(12) . .
O24 C28 C25B 112.5(14) . .
O25 C28 C25B 121.9(14) . .
O24 C28 C25A 123.0(14) . .
O25 C28 C25A 111.3(13) . .
C33 N31 C32 96(3) . .
C33 N31 H31A 112.5 . .
C32 N31 H31A 112.5 . .
C33 N31 H31B 112.5 . .
C32 N31 H31B 112.5 . .
H31A N31 H31B 110.0 . .
N31 C33 H33A 109.5 . .
N31 C33 H33B 109.5 . .
H33A C33 H33B 109.5 . .
N31 C33 H33C 109.5 . .
H33A C33 H33C 109.5 . .
H33B C33 H33C 109.5 . .
O12 Zn1 O22 117.8(3) 7_556 .
O12 Zn1 O25 111.2(4) 7_556 4_545
O22 Zn1 O25 106.7(4) . 4_545
O12 Zn1 O11 112.1(3) 7_556 .
O22 Zn1 O11 101.1(3) . .
O25 Zn1 O11 107.0(3) 4_545 .
O12 Zn1 Zn2 150.8(2) 7_556 .
O22 Zn1 Zn2 78.7(2) . .
O25 Zn1 Zn2 83.7(2) 4_545 .
O11 Zn1 Zn2 38.73(18) . .
O14 Zn2 O11 116.6(3) 5_666 .
O14 Zn2 O23 139.6(3) 5_666 .
O11 Zn2 O23 103.7(3) . .
O14 Zn2 O24 85.0(3) 5_666 4_545
O11 Zn2 O24 93.1(3) . 4_545
O23 Zn2 O24 91.7(4) . 4_545
O14 Zn2 O1W 87.8(4) 5_666 .
O11 Zn2 O1W 95.8(3) . .
O23 Zn2 O1W 89.7(4) . .
O24 Zn2 O1W 170.4(4) 4_545 .
O14 Zn2 Zn1 141.2(2) 5_666 .
O11 Zn2 Zn1 38.45(18) . .
O23 Zn2 Zn1 73.1(2) . .
O24 Zn2 Zn1 71.4(2) 4_545 .
O1W Zn2 Zn1 118.0(3) . .
C11 O11 Zn1 126.3(6) . .
C11 O11 Zn2 125.8(6) . .
Zn1 O11 Zn2 102.8(3) . .
C18 O14 Zn2 115.4(7) . 5_666
C17 O12 Zn1 121.9(7) . 7_556
C28 O25 Zn1 123.2(8) . 4
O14 C18 O15 122.0(9) . .
O14 C18 C15 116.9(9) . .
O15 C18 C15 121.1(9) . .
C13 C15 C16 118.7(9) . .
C13 C15 C18 119.8(9) . .
C16 C15 C18 121.4(9) . .
C27 O23 Zn2 132.9(8) . .
O12 C17 O13 118.6(9) . .
O12 C17 C14 122.2(9) . .
O13 C17 C14 119.2(9) . .
O11 C11 C13 120.6(9) . .
O11 C11 C12 121.2(9) . .
C13 C11 C12 118.2(9) . .
C28 O24 Zn2 135.1(8) . 4
C14 C16 C15 121.2(10) . .
C14 C16 H16 119.4 . .
C15 C16 H16 119.4 . .
C15 C13 C11 122.3(9) . .
C15 C13 H13 118.8 . .
C11 C13 H13 118.8 . .
C27 O22 Zn1 125.5(8) . .
C14 C12 C11 119.7(9) . .
C14 C12 H12 120.1 . .
C11 C12 H12 120.1 . .
C16 C14 C12 119.9(10) . .
C16 C14 C17 124.0(10) . .
C12 C14 C17 116.1(9) . .
N31 C32 H32A 109.5 . .
N31 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
N31 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O21A C21A 1.37(3) .
C21A C22A 1.3900 .
C21A C23A 1.3900 .
C22A C24A 1.3900 .
C22A H22A 0.9500 .
C24A C26A 1.3900 .
C24A C27 1.44(2) .
C26A C25A 1.3900 .
C26A H26A 0.9500 .
C25A C23A 1.3900 .
C25A C28 1.57(2) .
C23A H23A 0.9500 .
O21B C21B 1.30(2) .
O21B O21B 1.57(5) 2
C21B C22B 1.3900 .
C21B C23B 1.3900 .
C22B C24B 1.3900 .
C22B H22B 0.9500 .
C24B C26B 1.3900 .
C24B C27 1.52(2) .
C26B C25B 1.3900 .
C26B H26B 0.9500 .
C25B C23B 1.3900 .
C25B C28 1.44(2) .
C23B H23B 0.9500 .
C27 O23 1.230(14) .
C27 O22 1.299(13) .
C28 O24 1.255(14) .
C28 O25 1.268(14) .
N31 C33 1.61(4) .
N31 C32 1.77(4) .
N31 H31A 0.9900 .
N31 H31B 0.9900 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
Zn1 O12 1.905(7) 7_556
Zn1 O22 1.939(8) .
Zn1 O25 1.959(8) 4_545
Zn1 O11 1.981(6) .
Zn1 Zn2 3.1064(16) .
Zn2 O14 1.968(7) 5_666
Zn2 O11 1.993(6) .
Zn2 O23 2.011(8) .
Zn2 O24 2.077(9) 4_545
Zn2 O1W 2.131(9) .
O11 C11 1.363(11) .
O14 C18 1.272(11) .
O14 Zn2 1.968(7) 5_666
O12 C17 1.232(12) .
O12 Zn1 1.905(7) 7_556
O25 Zn1 1.959(8) 4
C18 O15 1.276(13) .
C18 C15 1.475(14) .
C15 C13 1.361(13) .
C15 C16 1.403(14) .
C17 O13 1.294(13) .
C17 C14 1.436(15) .
C11 C13 1.400(13) .
C11 C12 1.420(14) .
O24 Zn2 2.076(9) 4
C16 C14 1.382(15) .
C16 H16 0.9500 .
C13 H13 0.9500 .
C12 C14 1.391(14) .
C12 H12 0.9500 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
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
N31 H31B O15 0.99 2.45 3.08(4) 121.5 8_455
N31 H31B O1W 0.99 2.45 3.23(4) 135.1 4_545
C13 H13 O14 0.95 2.36 3.225(12) 151.9 5_666
C12 H12 O12 0.95 2.37 3.159(12) 139.8 7_556
