#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:49:32 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179675 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/27/4512703.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_4512703
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         'C20 H22 N2 O10 Zn2'
_chemical_formula_sum            'C20 H22 N2 O10 Zn2'
_chemical_formula_weight         581.13
_chemical_melting_point          ?
_chemical_name_common            'compound 4'
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 108.46(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.808(3)
_cell_length_b                   12.964(3)
_cell_length_c                   14.513(3)
_cell_measurement_reflns_used    8145
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0
_cell_measurement_theta_min      3.0
_cell_volume                     2999.6(12)
_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 3.0 (Crystal Impact)'
_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 0.995
_diffrn_measured_fraction_theta_max 0.879
_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  0.0280
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            20934
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.089
_diffrn_reflns_theta_min         2.828
_diffrn_source                   'Rotating anode'
_exptl_absorpt_coefficient_mu    1.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear 3.1 (Rigaku 2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.028
_exptl_crystal_size_mid          0.023
_exptl_crystal_size_min          0.014
_refine_diff_density_max         1.360
_refine_diff_density_min         -1.179
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         7752
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0577
_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)+(0.0862P)²+6.4195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.1689
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6980
_reflns_number_total             7752
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg501808y_si_004.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.

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               4512703
#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   0.955
_shelx_estimated_absorpt_t_max   0.977
_shelxl_version_number           2013-4
#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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O25 O 0.2266(3) 0.8788(4) 0.5340(4) 0.0935(19) Uani 1 1 d . . . . .
N41 N 0.3418(9) 0.7190(12) 0.5703(11) 0.102(4) Uiso 0.5 1 d D . P A 1
H41A H 0.3000 0.7739 0.5665 0.123 Uiso 0.5 1 calc R U P A 1
H41B H 0.3620 0.6967 0.6391 0.123 Uiso 0.5 1 calc R U P A 1
C42 C 0.2932(18) 0.6298(18) 0.515(2) 0.182(12) Uiso 0.5 1 d D . P A 1
H42A H 0.2473 0.6130 0.5408 0.274 Uiso 0.5 1 calc R U P A 1
H42B H 0.3302 0.5700 0.5225 0.274 Uiso 0.5 1 calc R U P A 1
H42C H 0.2700 0.6480 0.4464 0.274 Uiso 0.5 1 calc R U P A 1
C43 C 0.4126(15) 0.770(2) 0.553(2) 0.184(12) Uiso 0.5 1 d D . P A 1
H43A H 0.4293 0.8297 0.5964 0.276 Uiso 0.5 1 calc R U P A 1
H43B H 0.3967 0.7931 0.4854 0.276 Uiso 0.5 1 calc R U P A 1
H43C H 0.4597 0.7217 0.5659 0.276 Uiso 0.5 1 calc R U P A 1
N51 N 0.3893(13) 0.8507(17) 0.6694(14) 0.155(7) Uiso 0.5 1 d D . P B 2
H51A H 0.4011 0.7856 0.7069 0.186 Uiso 0.5 1 calc R U P B 2
H51B H 0.3289 0.8489 0.6316 0.186 Uiso 0.5 1 calc R U P B 2
C53 C 0.398(2) 0.933(2) 0.742(2) 0.185(12) Uiso 0.5 1 d D . P B 2
H53A H 0.3616 0.9187 0.7816 0.278 Uiso 0.5 1 calc R U P B 2
H53B H 0.3824 0.9998 0.7093 0.278 Uiso 0.5 1 calc R U P B 2
H53C H 0.4567 0.9367 0.7848 0.278 Uiso 0.5 1 calc R U P B 2
C52 C 0.4339(9) 0.8419(12) 0.5969(11) 0.079(4) Uiso 0.5 1 d D . P B 2
H52A H 0.4150 0.7797 0.5577 0.119 Uiso 0.5 1 calc R U P B 2
H52B H 0.4944 0.8374 0.6303 0.119 Uiso 0.5 1 calc R U P B 2
H52C H 0.4219 0.9027 0.5546 0.119 Uiso 0.5 1 calc R U P B 2
N31 N 0.0904(7) 0.2841(8) 0.6711(8) 0.158(4) Uiso 1 1 d D . . C 3
H31A H 0.1445 0.3154 0.6724 0.189 Uiso 1 1 calc R U . C 3
H31B H 0.0859 0.2900 0.7373 0.189 Uiso 1 1 calc R U . C 3
C33 C 0.0921(9) 0.1730(9) 0.6470(11) 0.165(5) Uiso 1 1 d D . . C 3
H33A H 0.1398 0.1396 0.6949 0.248 Uiso 1 1 calc R U . C 3
H33B H 0.0976 0.1657 0.5821 0.248 Uiso 1 1 calc R U . C 3
H33C H 0.0399 0.1401 0.6482 0.248 Uiso 1 1 calc R U . C 3
C32 C 0.0209(9) 0.3454(12) 0.6032(11) 0.190(6) Uiso 1 1 d D . . C 3
H32A H 0.0252 0.4174 0.6246 0.284 Uiso 1 1 calc R U . C 3
H32B H -0.0332 0.3170 0.6029 0.284 Uiso 1 1 calc R U . C 3
H32C H 0.0252 0.3418 0.5375 0.284 Uiso 1 1 calc R U . C 3
Zn1 Zn 0.31802(2) 0.48702(3) 0.81944(3) 0.02213(12) Uani 1 1 d . . . D 2
Zn2 Zn 0.15464(2) 0.44689(3) 0.90055(3) 0.02353(12) Uani 1 1 d . . . D 2
O11 O 0.27256(13) 0.08506(19) 0.41379(18) 0.0266(5) Uani 1 1 d . . . D 2
O12 O 0.57631(16) 0.0588(2) 0.6163(2) 0.0347(6) Uani 1 1 d . . . D 2
O21 O -0.08846(16) 0.8223(2) 0.6406(2) 0.0369(6) Uani 1 1 d . . . D 2
O24 O 0.12231(19) 0.9886(2) 0.5038(2) 0.0432(7) Uani 1 1 d . . . D 2
O22 O 0.11563(17) 0.5427(2) 0.7886(3) 0.0465(8) Uani 1 1 d . . . D 2
O23 O 0.23154(17) 0.5864(2) 0.7554(2) 0.0433(7) Uani 1 1 d . . . D 2
C12 C 0.4078(2) 0.1103(3) 0.5329(3) 0.0312(7) Uani 1 1 d . . . D 2
H12 H 0.4316 0.0609 0.5011 0.037 Uiso 1 1 calc R U . D 2
O15 O 0.35698(18) 0.3847(3) 0.7464(2) 0.0467(8) Uani 1 1 d . . . D 2
C11 C 0.32246(19) 0.1340(3) 0.4945(2) 0.0261(6) Uani 1 1 d . . . D 2
C13 C 0.2889(2) 0.2093(3) 0.5418(3) 0.0313(7) Uani 1 1 d . . . D 2
H13 H 0.2312 0.2269 0.5167 0.038 Uiso 1 1 calc R U . D 2
C27 C 0.1563(2) 0.5988(3) 0.7501(3) 0.0306(7) Uani 1 1 d . . . D 2
C28 C 0.1600(2) 0.9067(3) 0.5429(4) 0.0424(10) Uani 1 1 d . . . D 2
C25 C 0.1157(2) 0.8427(3) 0.5987(3) 0.0361(8) Uani 1 1 d . . . D 2
C23 C 0.0343(2) 0.8672(3) 0.5963(3) 0.0340(8) Uani 1 1 d . . . D 2
H23 H 0.0085 0.9284 0.5645 0.041 Uiso 1 1 calc R U . D 2
C26 C 0.1556(2) 0.7546(3) 0.6480(3) 0.0396(9) Uani 1 1 d . . . D 2
H26 H 0.2114 0.7386 0.6507 0.048 Uiso 1 1 calc R U . D 2
C16 C 0.4244(2) 0.2317(3) 0.6636(3) 0.0388(9) Uani 1 1 d . . . D 2
H16 H 0.4586 0.2639 0.7213 0.047 Uiso 1 1 calc R U . D 2
C18 C 0.3048(2) 0.3381(3) 0.6773(3) 0.0381(8) Uani 1 1 d . . . D 2
C17 C 0.5484(2) 0.1244(3) 0.6637(3) 0.0396(9) Uani 1 1 d . . . D 2
C21 C -0.0100(2) 0.8025(3) 0.6406(3) 0.0305(7) Uani 1 1 d . . . D 2
O14 O 0.2283(2) 0.3552(3) 0.6501(3) 0.0730(13) Uani 1 1 d . . . D 2
C14 C 0.4584(2) 0.1579(3) 0.6174(3) 0.0346(8) Uani 1 1 d . . . D 2
C15 C 0.3399(2) 0.2581(3) 0.6252(3) 0.0335(8) Uani 1 1 d . . . D 2
C22 C 0.0306(2) 0.7136(3) 0.6877(3) 0.0338(8) Uani 1 1 d . . . D 2
H22 H 0.0013 0.6678 0.7167 0.041 Uiso 1 1 calc R U . D 2
C24 C 0.1127(2) 0.6909(3) 0.6928(3) 0.0330(8) Uani 1 1 d . . . D 2
O13 O 0.5899(2) 0.1582(4) 0.7434(3) 0.0935(19) Uani 1 1 d . . . D 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'
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
C43 N41 C42 127(2) . .
C43 N41 H41A 105.6 . .
C42 N41 H41A 105.6 . .
C43 N41 H41B 105.6 . .
C42 N41 H41B 105.6 . .
H41A N41 H41B 106.1 . .
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 . .
C52 N51 C53 127(2) . .
C52 N51 H51A 105.5 . .
C53 N51 H51A 105.5 . .
C52 N51 H51B 105.5 . .
C53 N51 H51B 105.5 . .
H51A N51 H51B 106.1 . .
N51 C53 H53A 109.5 . .
N51 C53 H53B 109.5 . .
H53A C53 H53B 109.5 . .
N51 C53 H53C 109.5 . .
H53A C53 H53C 109.5 . .
H53B C53 H53C 109.5 . .
N51 C52 H52A 109.5 . .
N51 C52 H52B 109.5 . .
H52A C52 H52B 109.5 . .
N51 C52 H52C 109.5 . .
H52A C52 H52C 109.5 . .
H52B C52 H52C 109.5 . .
C33 N31 C32 115.4(12) . .
C33 N31 H31A 108.4 . .
C32 N31 H31A 108.4 . .
C33 N31 H31B 108.4 . .
C32 N31 H31B 108.4 . .
H31A N31 H31B 107.5 . .
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 . .
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 . .
O15 Zn1 O23 121.55(15) . .
O15 Zn1 O12 99.98(13) . 2_656
O23 Zn1 O12 109.90(13) . 2_656
O15 Zn1 O11 108.90(13) . 4_566
O23 Zn1 O11 104.29(11) . 4_566
O12 Zn1 O11 112.42(11) 2_656 4_566
O24 Zn2 O21 108.82(12) 4_576 2_546
O24 Zn2 O11 122.28(12) 4_576 4_566
O21 Zn2 O11 108.34(11) 2_546 4_566
O24 Zn2 O22 105.20(15) 4_576 .
O21 Zn2 O22 105.05(14) 2_546 .
O11 Zn2 O22 105.81(11) 4_566 .
C11 O11 Zn2 120.5(2) . 4_565
C11 O11 Zn1 122.81(19) . 4_565
Zn2 O11 Zn1 115.16(11) 4_565 4_565
C17 O12 Zn1 119.5(2) . 2_646
C21 O21 Zn2 128.7(2) . 2_556
C28 O24 Zn2 118.9(3) . 4_575
C27 O22 Zn2 130.3(2) . .
C27 O23 Zn1 134.6(3) . .
C14 C12 C11 121.1(3) . .
C14 C12 H12 119.5 . .
C11 C12 H12 119.5 . .
C18 O15 Zn1 119.6(2) . .
O11 C11 C12 121.0(3) . .
O11 C11 C13 120.6(3) . .
C12 C11 C13 118.4(3) . .
C15 C13 C11 120.4(3) . .
C15 C13 H13 119.8 . .
C11 C13 H13 119.8 . .
O22 C27 O23 125.7(3) . .
O22 C27 C24 118.0(3) . .
O23 C27 C24 116.3(3) . .
O25 C28 O24 122.9(4) . .
O25 C28 C25 121.1(4) . .
O24 C28 C25 116.0(3) . .
C23 C25 C26 120.3(3) . .
C23 C25 C28 120.5(3) . .
C26 C25 C28 119.0(3) . .
C25 C23 C21 120.7(3) . .
C25 C23 H23 119.6 . .
C21 C23 H23 119.6 . .
C24 C26 C25 119.3(3) . .
C24 C26 H26 120.3 . .
C25 C26 H26 120.3 . .
C14 C16 C15 119.9(3) . .
C14 C16 H16 120.1 . .
C15 C16 H16 120.1 . .
O14 C18 O15 123.9(4) . .
O14 C18 C15 119.6(4) . .
O15 C18 C15 116.4(3) . .
O13 C17 O12 123.5(4) . .
O13 C17 C14 120.4(4) . .
O12 C17 C14 116.1(3) . .
O21 C21 C22 118.9(3) . .
O21 C21 C23 123.3(3) . .
C22 C21 C23 117.8(3) . .
C16 C14 C12 119.9(3) . .
C16 C14 C17 119.3(3) . .
C12 C14 C17 120.6(3) . .
C13 C15 C16 120.3(3) . .
C13 C15 C18 121.1(3) . .
C16 C15 C18 118.6(3) . .
C24 C22 C21 121.5(3) . .
C24 C22 H22 119.3 . .
C21 C22 H22 119.3 . .
C26 C24 C22 120.2(3) . .
C26 C24 C27 119.7(3) . .
C22 C24 C27 120.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O25 C28 1.222(5) .
N41 C43 1.451(10) .
N41 C42 1.493(10) .
N41 H41A 0.9900 .
N41 H41B 0.9900 .
C42 H42A 0.9800 .
C42 H42B 0.9800 .
C42 H42C 0.9800 .
C43 H43A 0.9800 .
C43 H43B 0.9800 .
C43 H43C 0.9800 .
N51 C52 1.476(9) .
N51 C53 1.483(10) .
N51 H51A 0.9900 .
N51 H51B 0.9900 .
C53 H53A 0.9800 .
C53 H53B 0.9800 .
C53 H53C 0.9800 .
C52 H52A 0.9800 .
C52 H52B 0.9800 .
C52 H52C 0.9800 .
N31 C33 1.486(8) .
N31 C32 1.495(9) .
N31 H31A 0.9900 .
N31 H31B 0.9900 .
C33 H33A 0.9800 .
C33 H33B 0.9800 .
C33 H33C 0.9800 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
Zn1 O15 1.937(3) .
Zn1 O23 1.944(3) .
Zn1 O12 1.960(3) 2_656
Zn1 O11 1.999(2) 4_566
Zn2 O24 1.938(3) 4_576
Zn2 O21 1.945(2) 2_546
Zn2 O11 1.974(2) 4_566
Zn2 O22 1.984(3) .
O11 C11 1.362(4) .
O11 Zn2 1.974(2) 4_565
O11 Zn1 1.999(2) 4_565
O12 C17 1.273(4) .
O12 Zn1 1.960(3) 2_646
O21 C21 1.343(4) .
O21 Zn2 1.945(2) 2_556
O24 C28 1.274(5) .
O24 Zn2 1.938(3) 4_575
O22 C27 1.246(4) .
O23 C27 1.252(4) .
C12 C14 1.395(5) .
C12 C11 1.398(4) .
C12 H12 0.9500 .
O15 C18 1.259(5) .
C11 C13 1.410(5) .
C13 C15 1.393(5) .
C13 H13 0.9500 .
C27 C24 1.505(5) .
C28 C25 1.509(5) .
C25 C23 1.396(5) .
C25 C26 1.401(5) .
C23 C21 1.405(5) .
C23 H23 0.9500 .
C26 C24 1.387(5) .
C26 H26 0.9500 .
C16 C14 1.391(5) .
C16 C15 1.394(5) .
C16 H16 0.9500 .
C18 O14 1.239(5) .
C18 C15 1.509(5) .
C17 O13 1.227(5) .
C17 C14 1.512(5) .
C21 C22 1.402(5) .
C22 C24 1.389(5) .
C22 H22 0.9500 .
