#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/46/4314626.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_4314626
loop_
_publ_author_name
'Ryosuke Ohshima'
'Masanori Kitamura'
'Akinori Morita'
'Motoo Shiro'
'Yasuyuki Yamada'
'Masahiko Ikekita'
'Eiichi Kimura'
'Shin Aoki'
_publ_section_title
;
 Design and Synthesis of a Fluorescent Probe for Zn2+,
 5,7-Bis(N,N-dimethylaminosulfonyl)-8-hydroxyquinoline-Pendant
 1,4,7,10-Tetraazacyclododecane and Zn2+-Dependent Hydrolytic and
 Zn2+-Independent Photochemical Reactivation of Its Benzenesulfonyl-Caged
 Derivative
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              888
_journal_page_last               899
_journal_paper_doi               10.1021/ic901279t
_journal_volume                  49
_journal_year                    2010
_chemical_formula_moiety         'C22 H34 N7 O5 S2 Zn, H2 O, N O3 '
_chemical_formula_sum            'C22 H36 N8 O9 S2 Zn'
_chemical_formula_weight         686.07
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90.0000
_cell_angle_beta                 93.923(3)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   11.602(5)
_cell_length_b                   13.792(6)
_cell_length_c                   17.941(8)
_cell_measurement_reflns_used    6408
_cell_measurement_temperature    133.1
_cell_measurement_theta_max      25.3
_cell_measurement_theta_min      3.1
_cell_volume                     2864(2)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  SHELXL
_computing_structure_solution    SIR2004
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.091
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22048
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_exptl_absorpt_coefficient_mu    1.068
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.676
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1432.00
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.04
_refine_diff_density_min         -0.83
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     380
_refine_ls_number_reflns         7339
_refine_ls_R_factor_gt           0.0646
_refine_ls_shift/su_max          0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0922P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1901
_reflns_number_gt                4307
_reflns_number_total             7339
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ic901279t_si_002_1.cif
_cod_data_source_block           11
_cod_original_formula_sum        'C22 H36 N8 O9 S2 Zn '
_cod_database_code               4314626
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn(1) Zn 0.77423(4) 0.27214(3) 0.41458(3) 0.01998(15) Uani 1.00 1 d . . .
S(1) S 0.29186(9) -0.03525(8) 0.38047(6) 0.0210(2) Uani 1.00 1 d . . .
S(2) S 0.33960(9) 0.34364(7) 0.44934(6) 0.0203(2) Uani 1.00 1 d . . .
O(1) O 0.5971(2) 0.3058(2) 0.42357(18) 0.0237(6) Uani 1.00 1 d . . .
O(2) O 0.3345(2) -0.1191(2) 0.42276(18) 0.0269(7) Uani 1.00 1 d . . .
O(3) O 0.1762(2) -0.0037(2) 0.39377(18) 0.0287(7) Uani 1.00 1 d . . .
O(4) O 0.2162(2) 0.3306(2) 0.4335(2) 0.0322(8) Uani 1.00 1 d . . .
O(5) O 0.3914(2) 0.4256(2) 0.41635(18) 0.0298(7) Uani 1.00 1 d . . .
O(6) O 0.4944(3) 0.2211(3) 0.2264(2) 0.0514(11) Uani 1.00 1 d . . .
O(7) O 0.6642(3) 0.1579(2) 0.2278(2) 0.0452(9) Uani 1.00 1 d . . .
O(8) O 0.6429(2) 0.3132(2) 0.2126(2) 0.0341(8) Uani 1.00 1 d . . .
O(9) O 0.5454(2) 0.4661(2) 0.29464(19) 0.0368(8) Uani 1.00 1 d . . .
N(1) N 0.8478(3) 0.2557(2) 0.5259(2) 0.0198(7) Uani 1.00 1 d . . .
N(2) N 0.7888(2) 0.4278(2) 0.4473(2) 0.0240(8) Uani 1.00 1 d . . .
N(3) N 0.8551(3) 0.3273(2) 0.3205(2) 0.0249(8) Uani 1.00 1 d . . .
N(4) N 0.9241(2) 0.1526(2) 0.3987(2) 0.0215(7) Uani 1.00 1 d . . .
N(5) N 0.6919(2) 0.1382(2) 0.39286(19) 0.0174(7) Uani 1.00 1 d . . .
N(6) N 0.3061(3) -0.0622(2) 0.2921(2) 0.0236(8) Uani 1.00 1 d . . .
N(7) N 0.3593(3) 0.3552(2) 0.5403(2) 0.0295(9) Uani 1.00 1 d . . .
N(8) N 0.5996(3) 0.2300(2) 0.2222(2) 0.0266(8) Uani 1.00 1 d . . .
C(1) C 0.9733(3) 0.1329(3) 0.4754(2) 0.0246(9) Uani 1.00 1 d . . .
C(2) C 0.9682(3) 0.2217(3) 0.5259(2) 0.0233(9) Uani 1.00 1 d . . .
C(3) C 0.8360(3) 0.3483(3) 0.5671(2) 0.0252(9) Uani 1.00 1 d . . .
C(4) C 0.8643(3) 0.4327(3) 0.5167(2) 0.0266(10) Uani 1.00 1 d . . .
C(5) C 0.8296(3) 0.4839(3) 0.3844(2) 0.0307(11) Uani 1.00 1 d . . .
C(6) C 0.9119(4) 0.4219(3) 0.3420(2) 0.0316(11) Uani 1.00 1 d . . .
C(7) C 0.9348(4) 0.2561(3) 0.2893(2) 0.0301(10) Uani 1.00 1 d . . .
C(8) C 1.0044(3) 0.2013(3) 0.3509(2) 0.0258(9) Uani 1.00 1 d . . .
C(9) C 0.8723(3) 0.0646(3) 0.3639(2) 0.0258(10) Uani 1.00 1 d . . .
C(10) C 0.7446(3) 0.0575(3) 0.3759(2) 0.0216(9) Uani 1.00 1 d . . .
C(11) C 0.6844(3) -0.0301(3) 0.3656(2) 0.0241(9) Uani 1.00 1 d . . .
C(12) C 0.5683(3) -0.0326(3) 0.3725(2) 0.0228(9) Uani 1.00 1 d . . .
C(13) C 0.5074(3) 0.0541(3) 0.3887(2) 0.0176(8) Uani 1.00 1 d . . .
C(14) C 0.3849(3) 0.0629(3) 0.3950(2) 0.0195(8) Uani 1.00 1 d . . .
C(15) C 0.3387(3) 0.1521(3) 0.4124(2) 0.0210(9) Uani 1.00 1 d . . .
C(16) C 0.4065(3) 0.2359(3) 0.4235(2) 0.0197(8) Uani 1.00 1 d . . .
C(17) C 0.5283(3) 0.2333(2) 0.4165(2) 0.0180(8) Uani 1.00 1 d . . .
C(18) C 0.5755(3) 0.1381(3) 0.3991(2) 0.0183(8) Uani 1.00 1 d . . .
C(19) C 0.2692(4) 0.0165(3) 0.2391(2) 0.0368(12) Uani 1.00 1 d . . .
C(20) C 0.2561(4) -0.1575(3) 0.2695(2) 0.0331(11) Uani 1.00 1 d . . .
C(21) C 0.2984(4) 0.2810(3) 0.5823(3) 0.0382(12) Uani 1.00 1 d . . .
C(22) C 0.4781(4) 0.3658(3) 0.5699(3) 0.0363(11) Uani 1.00 1 d . . .
H(1) H 1.0547 0.1122 0.4734 0.030 Uiso 1.00 1 c R . .
H(2) H 0.9301 0.0790 0.4970 0.030 Uiso 1.00 1 c R . .
H(3) H 0.9974 0.2046 0.5774 0.028 Uiso 1.00 1 c R . .
H(4) H 1.0177 0.2738 0.5075 0.028 Uiso 1.00 1 c R . .
H(5) H 0.8055 0.2087 0.5492 0.024 Uiso 1.00 1 c R . .
H(6) H 0.8894 0.3485 0.6125 0.030 Uiso 1.00 1 c R . .
H(7) H 0.7562 0.3550 0.5825 0.030 Uiso 1.00 1 c R . .
H(8) H 0.8520 0.4949 0.5426 0.032 Uiso 1.00 1 c R . .
H(9) H 0.9463 0.4293 0.5048 0.032 Uiso 1.00 1 c R . .
H(10) H 0.7159 0.4502 0.4573 0.029 Uiso 1.00 1 c R . .
H(11) H 0.8698 0.5432 0.4034 0.037 Uiso 1.00 1 c R . .
H(12) H 0.7629 0.5039 0.3504 0.037 Uiso 1.00 1 c R . .
H(13) H 0.9329 0.4565 0.2966 0.038 Uiso 1.00 1 c R . .
H(14) H 0.9835 0.4097 0.3738 0.038 Uiso 1.00 1 c R . .
H(15) H 0.7970 0.3403 0.2836 0.030 Uiso 1.00 1 c R . .
H(16) H 0.9883 0.2904 0.2577 0.036 Uiso 1.00 1 c R . .
H(17) H 0.8896 0.2093 0.2573 0.036 Uiso 1.00 1 c R . .
H(18) H 1.0547 0.1528 0.3287 0.031 Uiso 1.00 1 c R . .
H(19) H 1.0540 0.2470 0.3811 0.031 Uiso 1.00 1 c R . .
H(20) H 0.9124 0.0067 0.3856 0.031 Uiso 1.00 1 c R . .
H(21) H 0.8830 0.0655 0.3096 0.031 Uiso 1.00 1 c R . .
H(22) H 0.7245 -0.0876 0.3539 0.029 Uiso 1.00 1 c R . .
H(23) H 0.5276 -0.0922 0.3664 0.027 Uiso 1.00 1 c R . .
H(24) H 0.2578 0.1568 0.4171 0.025 Uiso 1.00 1 c R . .
H(25) H 0.2817 0.0795 0.2636 0.044 Uiso 1.00 1 c R . .
H(26) H 0.1870 0.0088 0.2238 0.044 Uiso 1.00 1 c R . .
H(27) H 0.3145 0.0131 0.1950 0.044 Uiso 1.00 1 c R . .
H(28) H 0.2297 -0.1557 0.2165 0.040 Uiso 1.00 1 c R . .
H(29) H 0.1906 -0.1718 0.2994 0.040 Uiso 1.00 1 c R . .
H(30) H 0.3150 -0.2080 0.2778 0.040 Uiso 1.00 1 c R . .
H(31) H 0.2921 0.2209 0.5531 0.046 Uiso 1.00 1 c R . .
H(32) H 0.2209 0.3044 0.5916 0.046 Uiso 1.00 1 c R . .
H(33) H 0.3418 0.2684 0.6301 0.046 Uiso 1.00 1 c R . .
H(34) H 0.5110 0.3017 0.5816 0.044 Uiso 1.00 1 c R . .
H(35) H 0.4805 0.4052 0.6154 0.044 Uiso 1.00 1 c R . .
H(36) H 0.5231 0.3977 0.5326 0.044 Uiso 1.00 1 c R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.125 0.123
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Zn Zn 0.284 1.430
;
International Tables for Crystallography
(1992, 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_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
O(1) Zn(1) N(1) 106.24(13) yes . . .
O(1) Zn(1) N(2) 79.98(11) yes . . .
O(1) Zn(1) N(3) 117.63(12) yes . . .
O(1) Zn(1) N(5) 77.10(11) yes . . .
N(1) Zn(1) N(2) 80.63(13) yes . . .
N(1) Zn(1) N(3) 127.73(13) yes . . .
N(1) Zn(1) N(5) 103.19(13) yes . . .
N(2) Zn(1) N(3) 80.48(14) yes . . .
N(2) Zn(1) N(5) 156.92(12) yes . . .
N(3) Zn(1) N(5) 112.73(13) yes . . .
O(2) S(1) O(3) 116.17(19) yes . . .
O(2) S(1) N(6) 105.68(18) yes . . .
O(2) S(1) C(14) 110.84(18) yes . . .
O(3) S(1) N(6) 112.48(18) yes . . .
O(3) S(1) C(14) 108.29(19) yes . . .
N(6) S(1) C(14) 102.55(19) yes . . .
O(4) S(2) O(5) 117.03(18) yes . . .
O(4) S(2) N(7) 106.0(2) yes . . .
O(4) S(2) C(16) 106.98(19) yes . . .
O(5) S(2) N(7) 107.55(19) yes . . .
O(5) S(2) C(16) 110.77(19) yes . . .
N(7) S(2) C(16) 108.2(2) yes . . .
Zn(1) O(1) C(17) 115.0(2) yes . . .
Zn(1) N(1) C(2) 110.7(2) yes . . .
Zn(1) N(1) C(3) 109.3(2) yes . . .
C(2) N(1) C(3) 113.1(3) yes . . .
Zn(1) N(2) C(4) 107.3(2) yes . . .
Zn(1) N(2) C(5) 109.1(2) yes . . .
C(4) N(2) C(5) 114.8(3) yes . . .
Zn(1) N(3) C(6) 108.5(2) yes . . .
Zn(1) N(3) C(7) 112.5(2) yes . . .
C(6) N(3) C(7) 113.4(3) yes . . .
C(1) N(4) C(8) 114.0(3) yes . . .
C(1) N(4) C(9) 111.3(3) yes . . .
C(8) N(4) C(9) 112.7(3) yes . . .
Zn(1) N(5) C(10) 125.0(2) yes . . .
Zn(1) N(5) C(18) 115.2(2) yes . . .
C(10) N(5) C(18) 119.8(3) yes . . .
S(1) N(6) C(19) 114.0(2) yes . . .
S(1) N(6) C(20) 113.6(3) yes . . .
C(19) N(6) C(20) 112.5(3) yes . . .
S(2) N(7) C(21) 113.6(3) yes . . .
S(2) N(7) C(22) 116.0(3) yes . . .
C(21) N(7) C(22) 111.0(3) yes . . .
O(6) N(8) O(7) 120.5(4) yes . . .
O(6) N(8) O(8) 120.0(3) yes . . .
O(7) N(8) O(8) 119.4(3) yes . . .
N(4) C(1) C(2) 112.1(3) yes . . .
N(1) C(2) C(1) 109.3(3) yes . . .
N(1) C(3) C(4) 109.3(3) yes . . .
N(2) C(4) C(3) 109.0(3) yes . . .
N(2) C(5) C(6) 109.4(3) yes . . .
N(3) C(6) C(5) 109.7(3) yes . . .
N(3) C(7) C(8) 111.6(3) yes . . .
N(4) C(8) C(7) 108.9(3) yes . . .
N(4) C(9) C(10) 111.5(3) yes . . .
N(5) C(10) C(9) 116.9(3) yes . . .
N(5) C(10) C(11) 121.6(3) yes . . .
C(9) C(10) C(11) 121.4(3) yes . . .
C(10) C(11) C(12) 119.8(3) yes . . .
C(11) C(12) C(13) 120.2(3) yes . . .
C(12) C(13) C(14) 126.2(3) yes . . .
C(12) C(13) C(18) 115.8(3) yes . . .
C(14) C(13) C(18) 117.9(3) yes . . .
S(1) C(14) C(13) 121.9(3) yes . . .
S(1) C(14) C(15) 118.6(3) yes . . .
C(13) C(14) C(15) 119.4(3) yes . . .
C(14) C(15) C(16) 122.7(3) yes . . .
S(2) C(16) C(15) 118.7(3) yes . . .
S(2) C(16) C(17) 120.2(3) yes . . .
C(15) C(16) C(17) 121.0(3) yes . . .
O(1) C(17) C(16) 125.9(3) yes . . .
O(1) C(17) C(18) 118.8(3) yes . . .
C(16) C(17) C(18) 115.3(3) yes . . .
N(5) C(18) C(13) 122.7(3) yes . . .
N(5) C(18) C(17) 113.7(3) yes . . .
C(13) C(18) C(17) 123.5(3) yes . . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
Zn(1) O(1) 2.123(2) yes . .
Zn(1) N(1) 2.129(3) yes . .
Zn(1) N(2) 2.229(3) yes . .
Zn(1) N(3) 2.126(3) yes . .
Zn(1) N(5) 2.103(3) yes . .
S(1) O(2) 1.451(3) yes . .
S(1) O(3) 1.446(2) yes . .
S(1) N(6) 1.648(3) yes . .
S(1) C(14) 1.740(4) yes . .
S(2) O(4) 1.452(3) yes . .
S(2) O(5) 1.428(3) yes . .
S(2) N(7) 1.641(4) yes . .
S(2) C(16) 1.753(4) yes . .
O(1) C(17) 1.280(4) yes . .
O(6) N(8) 1.234(5) yes . .
O(7) N(8) 1.245(5) yes . .
O(8) N(8) 1.269(5) yes . .
N(1) C(2) 1.475(5) yes . .
N(1) C(3) 1.486(5) yes . .
N(2) C(4) 1.474(5) yes . .
N(2) C(5) 1.473(6) yes . .
N(3) C(6) 1.500(6) yes . .
N(3) C(7) 1.485(6) yes . .
N(4) C(1) 1.479(5) yes . .
N(4) C(8) 1.471(5) yes . .
N(4) C(9) 1.473(5) yes . .
N(5) C(10) 1.315(5) yes . .
N(5) C(18) 1.364(4) yes . .
N(6) C(19) 1.487(6) yes . .
N(6) C(20) 1.482(5) yes . .
N(7) C(21) 1.479(6) yes . .
N(7) C(22) 1.450(5) yes . .
C(1) C(2) 1.526(6) yes . .
C(3) C(4) 1.523(6) yes . .
C(5) C(6) 1.524(6) yes . .
C(7) C(8) 1.523(6) yes . .
C(9) C(10) 1.514(5) yes . .
C(10) C(11) 1.402(6) yes . .
C(11) C(12) 1.362(5) yes . .
C(12) C(13) 1.429(5) yes . .
C(13) C(14) 1.439(5) yes . .
C(13) C(18) 1.406(5) yes . .
C(14) C(15) 1.386(5) yes . .
C(15) C(16) 1.405(5) yes . .
C(16) C(17) 1.428(5) yes . .
C(17) C(18) 1.465(5) yes . .
