#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512702.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_4512702
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         'C16 H6 O10 Zn2, 2(C2 H8 N)'
_chemical_formula_sum            'C20 H22 N2 O10 Zn2'
_chemical_formula_weight         581.13
_chemical_melting_point          ?
_chemical_name_common            pyridine
_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   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 91.296(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.3288(9)
_cell_length_b                   13.2643(8)
_cell_length_c                   14.3563(10)
_cell_measurement_reflns_used    23057
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2727.9(3)
_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 (Brandenberg, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            24711
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_min         3.072
_diffrn_source                   'Rotating anode'
_exptl_absorpt_coefficient_mu    1.808
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       Block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.088
_refine_diff_density_max         2.909
_refine_diff_density_min         -1.005
_refine_diff_density_rms         0.185
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         6358
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0631
_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)+(0.1095P)²+16.3705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1706
_refine_ls_wR_factor_ref         0.1715
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6236
_reflns_number_total             6358
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501808y_si_002.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_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4512702
#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   0.727
_shelx_estimated_absorpt_t_max   0.857
_shelxl_version_number           2014-3
#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
O11 O 0.5853(3) -0.3341(3) 0.3109(3) 0.0177(8) Uani 1 1 d . .
O13 O 0.2305(3) -0.1012(3) 0.3230(3) 0.0205(9) Uani 1 1 d . .
O21 O 0.2089(3) 0.0943(3) 0.1988(3) 0.0125(7) Uani 1 1 d . .
O14 O 0.3666(3) -0.4881(3) 0.5480(3) 0.0214(9) Uani 1 1 d . .
O12 O 0.3661(3) -0.0493(3) 0.2646(3) 0.0217(9) Uani 1 1 d . .
O23 O 0.1325(3) 0.4202(3) -0.0795(3) 0.0184(8) Uani 1 1 d . .
O25 O -0.0240(3) 0.4701(3) 0.2148(3) 0.0178(8) Uani 1 1 d . .
C17 C 0.3152(4) -0.1118(4) 0.3079(4) 0.0156(11) Uani 1 1 d . .
C13 C 0.4579(4) -0.3709(4) 0.4162(4) 0.0150(10) Uani 1 1 d . .
H13 H 0.4885 -0.4297 0.4394 0.018 Uiso 1 1 calc R U
C21 C 0.1726(4) 0.1825(4) 0.1669(4) 0.0135(10) Uani 1 1 d . .
C22 C 0.1995(4) 0.2224(4) 0.0822(4) 0.0134(10) Uani 1 1 d . .
H22 H 0.2455 0.1889 0.0469 0.016 Uiso 1 1 calc R U
C11 C 0.5004(4) -0.3138(4) 0.3474(4) 0.0176(11) Uani 1 1 d . .
O24 O -0.0355(4) 0.3405(4) 0.3126(4) 0.0395(14) Uani 1 1 d . .
O15 O 0.2664(4) -0.3637(4) 0.5778(4) 0.0392(15) Uani 1 1 d . .
C23 C 0.1076(4) 0.2356(4) 0.2201(4) 0.0122(10) Uani 1 1 d . .
H23 H 0.0893 0.2095 0.2786 0.015 Uiso 1 1 calc R U
O22 O 0.2513(3) 0.3120(4) -0.0878(3) 0.0253(10) Uani 1 1 d . .
C14 C 0.3634(4) -0.2040(4) 0.3468(4) 0.0155(11) Uani 1 1 d . .
C26 C 0.0949(4) 0.3635(4) 0.1003(4) 0.0157(11) Uani 1 1 d . .
H26 H 0.0678 0.4241 0.0769 0.019 Uiso 1 1 calc R U
C12 C 0.4508(4) -0.2285(5) 0.3140(5) 0.0217(13) Uani 1 1 d . .
H12 H 0.4780 -0.1871 0.2679 0.026 Uiso 1 1 calc R U
C16 C 0.3230(4) -0.2599(5) 0.4165(4) 0.0191(11) Uani 1 1 d . .
H16 H 0.2638 -0.2419 0.4398 0.023 Uiso 1 1 calc R U
C24 C 0.1591(4) 0.3121(4) 0.0484(4) 0.0146(10) Uani 1 1 d . .
C25 C 0.0694(4) 0.3268(4) 0.1875(4) 0.0126(10) Uani 1 1 d . .
C27 C 0.1845(4) 0.3494(4) -0.0477(4) 0.0162(11) Uani 1 1 d . .
C28 C -0.0023(4) 0.3801(5) 0.2438(4) 0.0183(11) Uani 1 1 d . .
C18 C 0.3302(5) -0.4004(5) 0.5307(5) 0.0230(13) Uani 1 1 d . .
C15 C 0.3719(4) -0.3439(5) 0.4518(4) 0.0183(11) Uani 1 1 d . .
N31 N 0.3470(4) 0.3179(5) 0.3035(4) 0.0312(14) Uani 1 1 d . .
H31A H 0.2904 0.2975 0.3240 0.037 Uiso 1 1 calc R U
H31B H 0.3722 0.2660 0.2711 0.037 Uiso 1 1 calc R U
N41 N 0.1582(6) 0.7008(6) 0.1305(6) 0.0450(18) Uani 1 1 d . .
H41A H 0.2137 0.7253 0.1109 0.054 Uiso 1 1 calc R U
H41B H 0.1235 0.7540 0.1499 0.054 Uiso 1 1 calc R U
C32 C 0.4085(7) 0.3417(8) 0.3847(6) 0.047(2) Uani 1 1 d . .
H32A H 0.4153 0.2819 0.4244 0.070 Uiso 1 1 calc R U
H32B H 0.4700 0.3624 0.3631 0.070 Uiso 1 1 calc R U
H32C H 0.3811 0.3967 0.4206 0.070 Uiso 1 1 calc R U
C42 C 0.1087(6) 0.6511(6) 0.0507(6) 0.0386(18) Uani 1 1 d . .
H42A H 0.0990 0.7000 0.0002 0.058 Uiso 1 1 calc R U
H42B H 0.1463 0.5947 0.0284 0.058 Uiso 1 1 calc R U
H42C H 0.0481 0.6259 0.0709 0.058 Uiso 1 1 calc R U
C43 C 0.1745(13) 0.6356(11) 0.2055(12) 0.110(7) Uani 1 1 d . .
H43A H 0.2071 0.6720 0.2559 0.165 Uiso 1 1 calc R U
H43B H 0.1148 0.6101 0.2278 0.165 Uiso 1 1 calc R U
H43C H 0.2130 0.5789 0.1853 0.165 Uiso 1 1 calc R U
C33 C 0.3338(8) 0.4070(7) 0.2397(8) 0.066(4) Uani 1 1 d . .
H33A H 0.2928 0.3880 0.1870 0.099 Uiso 1 1 calc R U
H33B H 0.3056 0.4626 0.2740 0.099 Uiso 1 1 calc R U
H33C H 0.3945 0.4283 0.2165 0.099 Uiso 1 1 calc R U
Zn1 Zn 0.33592(4) 0.04960(5) 0.16657(4) 0.01143(16) Uani 1 1 d . .
Zn2 Zn 0.15203(4) 0.01798(4) 0.29943(4) 0.00816(15) Uani 1 1 d . .
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'
Zn Zn 0.2839 1.4301 '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
C11 O11 Zn1 128.1(4) . 2_645
C17 O13 Zn2 128.2(4) . .
C21 O21 Zn2 122.1(3) . .
C21 O21 Zn1 121.9(3) . .
Zn2 O21 Zn1 114.74(18) . .
C18 O14 Zn1 116.5(4) . 4_556
C17 O12 Zn1 131.6(4) . .
C27 O23 Zn2 122.3(4) . 4_565
C28 O25 Zn2 123.5(4) . 2
O13 C17 O12 125.5(5) . .
O13 C17 C14 118.0(5) . .
O12 C17 C14 116.5(5) . .
C15 C13 C11 121.6(5) . .
C15 C13 H13 119.2 . .
C11 C13 H13 119.2 . .
O21 C21 C22 120.8(5) . .
O21 C21 C23 120.2(5) . .
C22 C21 C23 119.0(5) . .
C21 C22 C24 120.3(5) . .
C21 C22 H22 119.8 . .
C24 C22 H22 119.8 . .
O11 C11 C13 124.9(5) . .
O11 C11 C12 118.3(5) . .
C13 C11 C12 116.8(5) . .
C25 C23 C21 120.5(5) . .
C25 C23 H23 119.7 . .
C21 C23 H23 119.7 . .
C16 C14 C12 121.1(5) . .
C16 C14 C17 120.5(5) . .
C12 C14 C17 118.4(5) . .
C24 C26 C25 120.1(5) . .
C24 C26 H26 119.9 . .
C25 C26 H26 119.9 . .
C14 C12 C11 121.6(6) . .
C14 C12 H12 119.2 . .
C11 C12 H12 119.2 . .
C14 C16 C15 118.3(5) . .
C14 C16 H16 120.9 . .
C15 C16 H16 120.9 . .
C26 C24 C22 120.6(5) . .
C26 C24 C27 120.4(5) . .
C22 C24 C27 119.0(5) . .
C26 C25 C23 119.4(5) . .
C26 C25 C28 120.9(5) . .
C23 C25 C28 119.5(5) . .
O22 C27 O23 125.6(5) . .
O22 C27 C24 119.9(5) . .
O23 C27 C24 114.5(5) . .
O24 C28 O25 123.9(6) . .
O24 C28 C25 121.0(5) . .
O25 C28 C25 115.1(5) . .
O15 C18 O14 122.8(6) . .
O15 C18 C15 121.7(6) . .
O14 C18 C15 115.4(5) . .
C13 C15 C16 120.6(6) . .
C13 C15 C18 121.5(5) . .
C16 C15 C18 117.8(5) . .
C32 N31 C33 112.1(7) . .
C32 N31 H31A 109.2 . .
C33 N31 H31A 109.2 . .
C32 N31 H31B 109.2 . .
C33 N31 H31B 109.2 . .
H31A N31 H31B 107.9 . .
C43 N41 C42 112.8(8) . .
C43 N41 H41A 109.0 . .
C42 N41 H41A 109.0 . .
C43 N41 H41B 109.0 . .
C42 N41 H41B 109.0 . .
H41A N41 H41B 107.8 . .
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 . .
N41 C42 H42A 109.5 . .
N41 C42 H42B 109.5 . .
H42A C42 H42B 109.5 . .
N41 C42 H42C 109.5 . .
H42A C42 H42C 109.5 . .
H42B C42 H42C 109.5 . .
N41 C43 H43A 109.5 . .
N41 C43 H43B 109.5 . .
H43A C43 H43B 109.5 . .
N41 C43 H43C 109.5 . .
H43A C43 H43C 109.5 . .
H43B C43 H43C 109.5 . .
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 . .
O11 Zn1 O14 109.75(17) 2_655 4
O11 Zn1 O12 107.1(2) 2_655 .
O14 Zn1 O12 107.2(2) 4 .
O11 Zn1 O21 104.97(17) 2_655 .
O14 Zn1 O21 123.86(18) 4 .
O12 Zn1 O21 102.77(17) . .
O25 Zn2 O23 94.44(19) 2_545 4_566
O25 Zn2 O21 119.88(18) 2_545 .
O23 Zn2 O21 120.79(18) 4_566 .
O25 Zn2 O13 106.85(19) 2_545 .
O23 Zn2 O13 106.2(2) 4_566 .
O21 Zn2 O13 107.24(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O11 C11 1.363(7) .
O11 Zn1 1.934(4) 2_645
O13 C17 1.244(7) .
O13 Zn2 1.965(4) .
O21 C21 1.356(6) .
O21 Zn2 1.957(4) .
O21 Zn1 1.978(4) .
O14 C18 1.297(7) .
O14 Zn1 1.947(4) 4_556
O12 C17 1.276(7) .
O12 Zn1 1.964(4) .
O23 C27 1.277(7) .
O23 Zn2 1.948(4) 4_565
O25 C28 1.299(7) .
O25 Zn2 1.947(4) 2
C17 C14 1.505(7) .
C13 C15 1.391(8) .
C13 C11 1.397(8) .
C13 H13 0.9500 .
C21 C22 1.390(7) .
C21 C23 1.407(7) .
C22 C24 1.404(7) .
C22 H22 0.9500 .
C11 C12 1.413(8) .
O24 C28 1.225(8) .
O15 C18 1.248(8) .
C23 C25 1.404(7) .
C23 H23 0.9500 .
O22 C27 1.231(8) .
C14 C16 1.382(8) .
C14 C12 1.387(9) .
C26 C24 1.378(8) .
C26 C25 1.399(8) .
C26 H26 0.9500 .
C12 H12 0.9500 .
C16 C15 1.406(8) .
C16 H16 0.9500 .
C24 C27 1.518(8) .
C25 C28 1.499(8) .
C18 C15 1.493(8) .
N31 C32 1.480(9) .
N31 C33 1.505(13) .
N31 H31A 0.9100 .
N31 H31B 0.9100 .
N41 C43 1.397(15) .
N41 C42 1.487(11) .
N41 H41A 0.9100 .
N41 H41B 0.9100 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
Zn1 O11 1.934(4) 2_655
Zn1 O14 1.947(4) 4
Zn2 O25 1.947(4) 2_545
Zn2 O23 1.947(4) 4_566
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
C13 H13 O14 0.95 2.49 2.796(7) 98.6 .
N31 H31A O22 0.91 2.02 2.718(8) 132.8 4_566
N41 H41B O24 0.91 1.80 2.693(10) 168.1 2
