#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:32:51 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179667 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/20/4512010.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_4512010
loop_
_publ_author_name
'Ordonez, Carlos'
'Fonari, Marina'
'Lindline, Jennifer'
'Wei, Qiang'
'Timofeeva, Tatiana'
_publ_section_title
;
 How Structure-Directing Cations Tune the Fluorescence of Metal--Organic
 Frameworks
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5452
_journal_paper_doi               10.1021/cg5006133
_journal_volume                  14
_journal_year                    2014
_chemical_formula_moiety         'C9 H3 O6 Zn, C8 H20 N'
_chemical_formula_sum            'C17 H23 N O6 Zn'
_chemical_formula_weight         402.73
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.099(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.488(6)
_cell_length_b                   12.562(9)
_cell_length_c                   15.477(10)
_cell_measurement_reflns_used    1335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.97
_cell_measurement_theta_min      4.37
_cell_volume                     1772(2)
_computing_cell_refinement       'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_data_collection       'APEX2  (Bruker, 2005)'
_computing_data_reduction        'SAINT+ ver. 6.2 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_publication_material  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_refinement  'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_computing_structure_solution    'SHELXTL ver. 6.12 (Sheldrick, 2001)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0878
_diffrn_reflns_av_sigmaI/netI    0.0661
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11541
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         4.25
_exptl_absorpt_coefficient_mu    1.418
_exptl_absorpt_correction_T_max  0.9695
_exptl_absorpt_correction_T_min  0.8999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_crystal_colour            clear
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0510P)²+5.5873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1265
_reflns_number_gt                1861
_reflns_number_total             2539
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            Zn-BTC-Bu2NH2-M1.cif
_cod_data_source_block           zn-btc-bu2nh2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4512007--4512019.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4512010
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Zn1 Zn 0.68389(6) 0.05301(5) 0.08518(4) 0.0125(2) Uani 1 1 d .
O1 O 0.6700(4) -0.0518(3) -0.0114(3) 0.0232(10) Uani 1 1 d .
O5 O 0.7411(4) -0.0313(3) 0.1936(3) 0.0205(10) Uani 1 1 d .
O6 O 0.5188(4) -0.0572(3) 0.2140(3) 0.0271(10) Uani 1 1 d .
O2 O 0.5260(4) 0.1553(3) 0.0702(2) 0.0163(9) Uani 1 1 d .
O3 O 0.8664(4) 0.1146(3) 0.0723(2) 0.0145(9) Uani 1 1 d .
C7 C 0.6082(6) -0.1305(4) -0.0541(4) 0.0122(12) Uani 1 1 d .
O4 O 0.8455(4) 0.2397(3) 0.1692(3) 0.0319(11) Uani 1 1 d .
C6 C 0.6388(6) -0.2832(4) -0.1533(3) 0.0147(13) Uani 1 1 d .
H6A H 0.5407 -0.3005 -0.1612 0.018 Uiso 1 1 calc R
C1 C 0.7015(6) -0.2018(4) -0.0953(3) 0.0123(12) Uani 1 1 d .
C2 C 0.8486(6) -0.1767(4) -0.0815(4) 0.0165(13) Uani 1 1 d .
H2A H 0.8915 -0.1236 -0.0409 0.020 Uiso 1 1 calc R
C5 C 0.7205(6) -0.3394(4) -0.1998(4) 0.0146(13) Uani 1 1 d .
C8 C 0.6516(6) -0.0764(5) 0.2310(4) 0.0194(14) Uani 1 1 d .
C4 C 0.8667(6) -0.3119(4) -0.1866(4) 0.0179(13) Uani 1 1 d .
H4A H 0.9223 -0.3487 -0.2177 0.021 Uiso 1 1 calc R
C3 C 0.9318(6) -0.2309(4) -0.1284(4) 0.0150(13) Uani 1 1 d .
C9 C 0.9141(6) 0.1943(5) 0.1228(4) 0.0173(13) Uani 1 1 d .
N1 N 0.2493(5) -0.1342(4) 0.2186(3) 0.0293(13) Uani 1 1 d .
H1A H 0.2463 -0.1700 0.2684 0.035 Uiso 1 1 calc R
H1B H 0.3401 -0.1073 0.2276 0.035 Uiso 1 1 calc R
C10 C 0.1428(8) -0.0479(6) 0.2023(5) 0.0440(19) Uani 1 1 d .
H10A H 0.0444 -0.0768 0.1815 0.053 Uiso 1 1 calc R
H10B H 0.1584 -0.0013 0.1558 0.053 Uiso 1 1 calc R
C13 C 0.2934(10) 0.1471(6) 0.3995(5) 0.058(2) Uani 1 1 d .
H13A H 0.3873 0.1809 0.4215 0.087 Uiso 1 1 calc R
H13B H 0.2698 0.1098 0.4479 0.087 Uiso 1 1 calc R
H13C H 0.2199 0.2001 0.3759 0.087 Uiso 1 1 calc R
C11 C 0.1579(8) 0.0143(6) 0.2867(5) 0.048(2) Uani 1 1 d .
H11A H 0.0802 0.0671 0.2746 0.057 Uiso 1 1 calc R
H11B H 0.1406 -0.0339 0.3316 0.057 Uiso 1 1 calc R
C15 C 0.3238(9) -0.3014(6) 0.1505(6) 0.052(2) Uani 1 1 d .
H15A H 0.3238 -0.3389 0.2053 0.063 Uiso 1 1 calc R
H15B H 0.4210 -0.2717 0.1585 0.063 Uiso 1 1 calc R
C16 C 0.2920(9) -0.3815(7) 0.0722(5) 0.056(2) Uani 1 1 d .
H16A H 0.3024 -0.3460 0.0186 0.067 Uiso 1 1 calc R
H16B H 0.3638 -0.4385 0.0867 0.067 Uiso 1 1 calc R
C12 C 0.2983(8) 0.0701(7) 0.3269(5) 0.056(2) Uani 1 1 d .
H12A H 0.3266 0.1080 0.2798 0.067 Uiso 1 1 calc R
H12B H 0.3735 0.0174 0.3515 0.067 Uiso 1 1 calc R
C14 C 0.2147(9) -0.2122(6) 0.1362(5) 0.052(2) Uani 1 1 d .
H14A H 0.1171 -0.2414 0.1270 0.062 Uiso 1 1 calc R
H14B H 0.2164 -0.1730 0.0825 0.062 Uiso 1 1 calc R
C17 C 0.1442(11) -0.4274(7) 0.0533(7) 0.079(3) Uani 1 1 d .
H17A H 0.1283 -0.4752 0.0031 0.118 Uiso 1 1 calc R
H17B H 0.0727 -0.3713 0.0393 0.118 Uiso 1 1 calc R
H17C H 0.1350 -0.4656 0.1051 0.118 Uiso 1 1 calc R
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
O5 Zn1 O2 119.32(16) . .
O5 Zn1 O3 105.19(15) . .
O2 Zn1 O3 113.72(16) . .
O5 Zn1 O1 103.68(18) . .
O2 Zn1 O1 117.75(16) . .
O3 Zn1 O1 93.54(15) . .
C7 O1 Zn1 149.2(4) . .
C8 O5 Zn1 124.9(4) . .
C7 O2 Zn1 124.1(3) 3_655 .
C9 O3 Zn1 115.0(3) . .
O1 C7 O2 126.9(5) . 3_655
O1 C7 C1 116.7(5) . .
O2 C7 C1 116.3(5) 3_655 .
C1 C6 C5 120.7(5) . .
C1 C6 H6A 119.6 . .
C5 C6 H6A 119.6 . .
C6 C1 C2 120.1(5) . .
C6 C1 C7 120.8(5) . .
C2 C1 C7 118.7(5) . .
C3 C2 C1 120.0(5) . .
C3 C2 H2A 120.0 . .
C1 C2 H2A 120.0 . .
C4 C5 C6 118.4(5) . .
C4 C5 C8 119.7(5) . 4
C6 C5 C8 121.8(5) . 4
O6 C8 O5 125.4(5) . .
O6 C8 C5 120.0(5) . 4_556
O5 C8 C5 114.6(5) . 4_556
C5 C4 C3 121.7(5) . .
C5 C4 H4A 119.1 . .
C3 C4 H4A 119.1 . .
C4 C3 C2 119.0(5) . .
C4 C3 C9 120.7(5) . 3_755
C2 C3 C9 120.1(5) . 3_755
O4 C9 O3 124.4(5) . .
O4 C9 C3 118.9(5) . 3_755
O3 C9 C3 116.6(5) . 3_755
C10 N1 C14 110.2(5) . .
C10 N1 H1A 109.6 . .
C14 N1 H1A 109.6 . .
C10 N1 H1B 109.6 . .
C14 N1 H1B 109.6 . .
H1A N1 H1B 108.1 . .
N1 C10 C11 110.1(6) . .
N1 C10 H10A 109.6 . .
C11 C10 H10A 109.6 . .
N1 C10 H10B 109.6 . .
C11 C10 H10B 109.6 . .
H10A C10 H10B 108.1 . .
C12 C13 H13A 109.5 . .
C12 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C12 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C12 C11 C10 118.2(7) . .
C12 C11 H11A 107.8 . .
C10 C11 H11A 107.8 . .
C12 C11 H11B 107.8 . .
C10 C11 H11B 107.8 . .
H11A C11 H11B 107.1 . .
C14 C15 C16 113.3(7) . .
C14 C15 H15A 108.9 . .
C16 C15 H15A 108.9 . .
C14 C15 H15B 108.9 . .
C16 C15 H15B 108.9 . .
H15A C15 H15B 107.7 . .
C17 C16 C15 112.4(7) . .
C17 C16 H16A 109.1 . .
C15 C16 H16A 109.1 . .
C17 C16 H16B 109.1 . .
C15 C16 H16B 109.1 . .
H16A C16 H16B 107.9 . .
C11 C12 C13 114.3(7) . .
C11 C12 H12A 108.7 . .
C13 C12 H12A 108.7 . .
C11 C12 H12B 108.7 . .
C13 C12 H12B 108.7 . .
H12A C12 H12B 107.6 . .
C15 C14 N1 111.5(6) . .
C15 C14 H14A 109.3 . .
N1 C14 H14A 109.3 . .
C15 C14 H14B 109.3 . .
N1 C14 H14B 109.3 . .
H14A C14 H14B 108.0 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O5 1.931(4) .
Zn1 O2 1.938(4) .
Zn1 O3 1.957(4) .
Zn1 O1 1.969(4) .
O1 C7 1.242(6) .
O5 C8 1.285(7) .
O6 C8 1.237(7) .
O2 C7 1.267(6) 3_655
O3 C9 1.274(7) .
C7 O2 1.267(6) 3_655
C7 C1 1.519(7) .
O4 C9 1.236(7) .
C6 C1 1.381(8) .
C6 C5 1.389(8) .
C6 H6A 0.9300 .
C1 C2 1.389(8) .
C2 C3 1.389(8) .
C2 H2A 0.9300 .
C5 C4 1.388(8) .
C5 C8 1.517(8) 4
C8 C5 1.517(8) 4_556
C4 C3 1.386(8) .
C4 H4A 0.9300 .
C3 C9 1.512(8) 3_755
C9 C3 1.512(8) 3_755
N1 C10 1.456(8) .
N1 C14 1.569(9) .
N1 H1A 0.9000 .
N1 H1B 0.9000 .
C10 C11 1.494(10) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C13 C12 1.493(10) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C11 C12 1.481(10) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C15 C14 1.500(10) .
C15 C16 1.540(10) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C17 1.469(12) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
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
N1 H1A O4 0.90 1.86 2.683(6) 151.9 2_645
N1 H1B O6 0.90 1.87 2.753(6) 165.0 .
