#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:40:15 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179198 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/36/4313690.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_4313690
loop_
_publ_author_name
'David T. Puerta'
'Seth M. Cohen'
_publ_section_title
;
 Examination of Novel Zinc-Binding Groups for Use in Matrix
 Metalloproteinase Inhibitors
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              3423
_journal_page_last               3430
_journal_paper_doi               10.1021/ic026029g
_journal_volume                  42
_journal_year                    2003
_chemical_formula_sum            'C39 H36 B N6 O3 Zn'
_chemical_formula_weight         712.92
_chemical_name_common            TpZn(Maltol)
_chemical_name_systematic
;

  ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.6090(10)
_cell_angle_beta                 101.6060(10)
_cell_angle_gamma                93.2060(10)
_cell_formula_units_Z            2
_cell_length_a                   10.0442(8)
_cell_length_b                   10.3764(8)
_cell_length_c                   17.2365(14)
_cell_measurement_reflns_used    5990
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.61
_cell_volume                     1751.9(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  '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  0.0192
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14755
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.21
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             742
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .19
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7606
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0291
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0437P)²+0.6892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0804
_reflns_number_gt                7162
_reflns_number_total             7606
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic026029g_2.cif
_cod_data_source_block           Zn(hydrotrisblabla)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4313690
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C28 C 0.28654(16) 1.07360(15) 0.91950(9) 0.0278(3) Uani 1 1 d . . .
H28 H 0.2178 1.0774 0.9500 0.033 Uiso 1 1 calc R . .
C29 C 0.25714(15) 1.01277(14) 0.84330(9) 0.0257(3) Uani 1 1 d . . .
H29 H 0.1683 0.9740 0.8219 0.031 Uiso 1 1 calc R . .
C18 C 0.14431(16) 0.42770(15) 0.53467(10) 0.0304(3) Uani 1 1 d . . .
H18 H 0.0757 0.3616 0.5362 0.036 Uiso 1 1 calc R . .
C17 C 0.21108(16) 0.42693(15) 0.47167(10) 0.0295(3) Uani 1 1 d . . .
H17 H 0.1874 0.3605 0.4298 0.035 Uiso 1 1 calc R . .
Zn1 Zn 0.582909(15) 0.762990(14) 0.710095(9) 0.01741(6) Uani 1 1 d . . .
O1 O 0.47450(10) 0.74255(9) 0.79016(6) 0.0215(2) Uani 1 1 d . . .
O3 O 0.55135(10) 0.55202(9) 0.69930(6) 0.0209(2) Uani 1 1 d . . .
N2 N 0.79127(11) 0.76561(11) 0.72056(7) 0.0177(2) Uani 1 1 d . . .
N4 N 0.54012(11) 0.77863(11) 0.59095(7) 0.0182(2) Uani 1 1 d . . .
N6 N 0.60419(12) 0.97803(11) 0.72511(7) 0.0186(2) Uani 1 1 d . . .
N5 N 0.69767(12) 1.02663(11) 0.68426(7) 0.0185(2) Uani 1 1 d . . .
N1 N 0.84130(11) 0.84291(11) 0.66954(7) 0.0176(2) Uani 1 1 d . . .
C36 C 0.47412(14) 0.52078(13) 0.74497(8) 0.0196(3) Uani 1 1 d . . .
O2 O 0.31078(11) 0.46004(10) 0.85354(6) 0.0259(2) Uani 1 1 d . . .
N3 N 0.62796(12) 0.86420(11) 0.56450(7) 0.0187(2) Uani 1 1 d . . .
C31 C 0.43259(14) 0.62136(13) 0.79614(8) 0.0189(3) Uani 1 1 d . . .
C4 C 0.89492(14) 0.69963(13) 0.75574(8) 0.0182(3) Uani 1 1 d . . .
C14 C 0.45615(14) 0.72035(13) 0.52644(8) 0.0191(3) Uani 1 1 d . . .
C6 C 0.78225(14) 0.61898(14) 0.86268(8) 0.0219(3) Uani 1 1 d . . .
H6 H 0.7222 0.6868 0.8558 0.026 Uiso 1 1 calc R . .
B1 B 0.74851(16) 0.93889(15) 0.62263(9) 0.0188(3) Uani 1 1 d . . .
C32 C 0.35409(14) 0.58720(13) 0.84866(8) 0.0210(3) Uani 1 1 d . . .
C3 C 1.01264(14) 0.73513(13) 0.72777(8) 0.0205(3) Uani 1 1 d . . .
H3 H 1.1003 0.7034 0.7430 0.025 Uiso 1 1 calc R . .
C23 C 0.67656(14) 1.18263(13) 0.77292(8) 0.0213(3) Uani 1 1 d . . .
H23 H 0.6870 1.2626 0.8043 0.026 Uiso 1 1 calc R . .
C22 C 0.74302(14) 1.14930(13) 0.71270(8) 0.0202(3) Uani 1 1 d . . .
C2 C 0.97487(14) 0.82554(13) 0.67365(8) 0.0198(3) Uani 1 1 d . . .
C10 C 0.96822(14) 0.50797(13) 0.82739(8) 0.0216(3) Uani 1 1 d . . .
H10 H 1.0351 0.4994 0.7959 0.026 Uiso 1 1 calc R . .
C5 C 0.87981(14) 0.60725(13) 0.81552(8) 0.0190(3) Uani 1 1 d . . .
C9 C 0.95945(16) 0.42151(14) 0.88485(9) 0.0258(3) Uani 1 1 d . . .
H9 H 1.0204 0.3545 0.8927 0.031 Uiso 1 1 calc R . .
C15 C 0.34753(14) 0.62092(13) 0.53035(8) 0.0196(3) Uani 1 1 d . . .
C13 C 0.48887(14) 0.76853(14) 0.45790(8) 0.0225(3) Uani 1 1 d . . .
H13 H 0.4453 0.7441 0.4044 0.027 Uiso 1 1 calc R . .
C20 C 0.27873(14) 0.62191(14) 0.59327(8) 0.0224(3) Uani 1 1 d . . .
H20 H 0.3009 0.6890 0.6348 0.027 Uiso 1 1 calc R . .
C30 C 0.35735(15) 1.00852(13) 0.79821(9) 0.0225(3) Uani 1 1 d . . .
H30 H 0.3368 0.9661 0.7463 0.027 Uiso 1 1 calc R . .
C25 C 0.48774(14) 1.06610(13) 0.82864(8) 0.0202(3) Uani 1 1 d . . .
C8 C 0.86119(16) 0.43341(15) 0.93075(9) 0.0268(3) Uani 1 1 d . . .
H8 H 0.8546 0.3741 0.9698 0.032 Uiso 1 1 calc R . .
C24 C 0.59016(14) 1.07365(13) 0.77827(8) 0.0193(3) Uani 1 1 d . . .
C1 C 1.05829(15) 0.89653(15) 0.62499(9) 0.0264(3) Uani 1 1 d . . .
H1A H 1.0147 0.8820 0.5687 0.040 Uiso 1 1 calc R . .
H1B H 1.1498 0.8647 0.6334 0.040 Uiso 1 1 calc R . .
H1C H 1.0650 0.9893 0.6410 0.040 Uiso 1 1 calc R . .
C12 C 0.59734(14) 0.85868(14) 0.48416(8) 0.0214(3) Uani 1 1 d . . .
C33 C 0.30790(16) 0.67742(15) 0.90652(9) 0.0260(3) Uani 1 1 d . . .
H33A H 0.3392 0.7664 0.8998 0.039 Uiso 1 1 calc R . .
H33B H 0.3458 0.6555 0.9606 0.039 Uiso 1 1 calc R . .
H33C H 0.2082 0.6699 0.8973 0.039 Uiso 1 1 calc R . .
C26 C 0.51660(15) 1.12582(16) 0.90541(9) 0.0274(3) Uani 1 1 d . . .
H26 H 0.6052 1.1649 0.9269 0.033 Uiso 1 1 calc R . .
C7 C 0.77287(15) 0.53162(15) 0.91958(9) 0.0251(3) Uani 1 1 d . . .
H7 H 0.7056 0.5393 0.9509 0.030 Uiso 1 1 calc R . .
C16 C 0.31228(15) 0.52257(14) 0.46921(9) 0.0247(3) Uani 1 1 d . . .
H16 H 0.3576 0.5211 0.4259 0.030 Uiso 1 1 calc R . .
C21 C 0.84518(16) 1.22864(14) 0.67982(9) 0.0267(3) Uani 1 1 d . . .
H21A H 0.9356 1.1964 0.6964 0.040 Uiso 1 1 calc R . .
H21B H 0.8470 1.3194 0.6999 0.040 Uiso 1 1 calc R . .
H21C H 0.8196 1.2219 0.6217 0.040 Uiso 1 1 calc R . .
C34 C 0.34412(16) 0.36765(14) 0.80433(10) 0.0282(3) Uani 1 1 d . . .
H34 H 0.3114 0.2808 0.8074 0.034 Uiso 1 1 calc R . .
C19 C 0.17800(15) 0.52520(15) 0.59534(9) 0.0272(3) Uani 1 1 d . . .
H19 H 0.1322 0.5261 0.6385 0.033 Uiso 1 1 calc R . .
C11 C 0.67298(16) 0.94000(16) 0.43641(9) 0.0276(3) Uani 1 1 d . . .
H11A H 0.6726 1.0315 0.4544 0.041 Uiso 1 1 calc R . .
H11B H 0.6287 0.9265 0.3801 0.041 Uiso 1 1 calc R . .
H11C H 0.7672 0.9154 0.4434 0.041 Uiso 1 1 calc R . .
C35 C 0.42138(15) 0.39129(14) 0.75083(9) 0.0251(3) Uani 1 1 d . . .
H35 H 0.4410 0.3223 0.7169 0.030 Uiso 1 1 calc R . .
C27 C 0.41688(17) 1.12874(17) 0.95078(9) 0.0316(3) Uani 1 1 d . . .
H27 H 0.4380 1.1686 1.0033 0.038 Uiso 1 1 calc R . .
C39 C 0.07403(15) 0.91652(15) 1.04876(9) 0.0249(3) Uani 1 1 d . . .
H39 H 0.1247 0.8592 1.0821 0.030 Uiso 1 1 calc R . .
C38 C 0.00636(15) 0.87250(15) 0.97269(9) 0.0264(3) Uani 1 1 d . . .
H38 H 0.0108 0.7851 0.9540 0.032 Uiso 1 1 calc R . .
C37 C -0.06797(15) 0.95589(15) 0.92367(9) 0.0253(3) Uani 1 1 d . . .
H37 H -0.1144 0.9257 0.8715 0.030 Uiso 1 1 calc R . .
H40 H 0.8081(16) 0.9951(16) 0.5881(10) 0.018(4) Uiso 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'
B B 0.0013 0.0007 '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
_geom_angle_publ_flag
C27 C28 C29 119.65(14) . . ?
C28 C29 C30 120.19(14) . . ?
C19 C18 C17 119.73(14) . . ?
C18 C17 C16 120.54(14) . . ?
O1 Zn1 N4 134.73(5) . . ?
O1 Zn1 N2 129.69(4) . . ?
N4 Zn1 N2 95.51(4) . . ?
O1 Zn1 O3 81.15(4) . . ?
N4 Zn1 O3 94.07(4) . . ?
N2 Zn1 O3 94.90(4) . . ?
O1 Zn1 N6 95.38(4) . . ?
N4 Zn1 N6 87.63(4) . . ?
N2 Zn1 N6 88.12(4) . . ?
O3 Zn1 N6 176.38(4) . . ?
C31 O1 Zn1 113.89(8) . . ?
C36 O3 Zn1 107.71(8) . . ?
C4 N2 N1 106.78(11) . . ?
C4 N2 Zn1 138.20(9) . . ?
N1 N2 Zn1 114.25(8) . . ?
C14 N4 N3 106.92(11) . . ?
C14 N4 Zn1 138.26(9) . . ?
N3 N4 Zn1 114.47(8) . . ?
C24 N6 N5 105.85(11) . . ?
C24 N6 Zn1 139.01(9) . . ?
N5 N6 Zn1 110.95(8) . . ?
C22 N5 N6 110.68(11) . . ?
C22 N5 B1 128.60(11) . . ?
N6 N5 B1 120.34(11) . . ?
C2 N1 N2 109.77(11) . . ?
C2 N1 B1 130.09(11) . . ?
N2 N1 B1 119.98(11) . . ?
O3 C36 C35 124.77(13) . . ?
O3 C36 C31 119.02(12) . . ?
C35 C36 C31 116.21(12) . . ?
C34 O2 C32 119.25(11) . . ?
C12 N3 N4 109.43(11) . . ?
C12 N3 B1 129.09(12) . . ?
N4 N3 B1 121.18(11) . . ?
O1 C31 C32 122.72(13) . . ?
O1 C31 C36 118.04(12) . . ?
C32 C31 C36 119.24(13) . . ?
N2 C4 C3 109.63(12) . . ?
N2 C4 C5 122.30(12) . . ?
C3 C4 C5 128.05(13) . . ?
N4 C14 C13 109.66(12) . . ?
N4 C14 C15 123.21(12) . . ?
C13 C14 C15 127.13(13) . . ?
C7 C6 C5 120.19(14) . . ?
N5 B1 N3 110.91(11) . . ?
N5 B1 N1 106.91(11) . . ?
N3 B1 N1 110.31(11) . . ?
C31 C32 O2 121.73(13) . . ?
C31 C32 C33 125.63(13) . . ?
O2 C32 C33 112.63(12) . . ?
C2 C3 C4 105.82(12) . . ?
C22 C23 C24 105.68(12) . . ?
N5 C22 C23 107.47(12) . . ?
N5 C22 C21 123.25(13) . . ?
C23 C22 C21 129.27(13) . . ?
N1 C2 C3 108.00(11) . . ?
N1 C2 C1 122.49(13) . . ?
C3 C2 C1 129.51(13) . . ?
C9 C10 C5 120.71(13) . . ?
C10 C5 C6 118.97(13) . . ?
C10 C5 C4 119.20(12) . . ?
C6 C5 C4 121.80(12) . . ?
C8 C9 C10 119.75(14) . . ?
C16 C15 C20 119.00(13) . . ?
C16 C15 C14 118.89(13) . . ?
C20 C15 C14 122.11(12) . . ?
C12 C13 C14 105.84(12) . . ?
C19 C20 C15 120.36(13) . . ?
C29 C30 C25 120.46(13) . . ?
C26 C25 C30 118.92(13) . . ?
C26 C25 C24 120.22(13) . . ?
C30 C25 C24 120.65(13) . . ?
C7 C8 C9 120.09(13) . . ?
N6 C24 C23 110.31(12) . . ?
N6 C24 C25 123.22(12) . . ?
C23 C24 C25 126.22(13) . . ?
N3 C12 C13 108.14(12) . . ?
N3 C12 C11 123.14(13) . . ?
C13 C12 C11 128.72(13) . . ?
C27 C26 C25 120.59(14) . . ?
C8 C7 C6 120.28(14) . . ?
C17 C16 C15 120.15(14) . . ?
O2 C34 C35 123.53(13) . . ?
C18 C19 C20 120.21(14) . . ?
C34 C35 C36 119.93(14) . . ?
C28 C27 C26 120.17(14) . . ?
C38 C39 C37 120.16(14) . 2_577 ?
C39 C38 C37 120.19(14) . . ?
C39 C37 C38 119.64(14) 2_577 . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C28 C27 1.388(2) . ?
C28 C29 1.389(2) . ?
C29 C30 1.391(2) . ?
C18 C19 1.385(2) . ?
C18 C17 1.386(2) . ?
C17 C16 1.389(2) . ?
Zn1 O1 1.9367(10) . ?
Zn1 N4 2.0305(11) . ?
Zn1 N2 2.0626(12) . ?
Zn1 O3 2.1851(10) . ?
Zn1 N6 2.2233(12) . ?
O1 C31 1.3205(16) . ?
O3 C36 1.2554(17) . ?
N2 C4 1.3410(18) . ?
N2 N1 1.3750(15) . ?
N4 C14 1.3396(18) . ?
N4 N3 1.3784(15) . ?
N6 C24 1.3407(18) . ?
N6 N5 1.3746(15) . ?
N5 C22 1.3545(17) . ?
N5 B1 1.5383(18) . ?
N1 C2 1.3519(18) . ?
N1 B1 1.5545(19) . ?
C36 C35 1.4336(19) . ?
C36 C31 1.4566(19) . ?
O2 C34 1.3411(19) . ?
O2 C32 1.3791(17) . ?
N3 C12 1.3535(18) . ?
N3 B1 1.5426(19) . ?
C31 C32 1.3650(19) . ?
C4 C3 1.4033(19) . ?
C4 C5 1.4747(18) . ?
C14 C13 1.4020(19) . ?
C14 C15 1.4737(19) . ?
C6 C7 1.390(2) . ?
C6 C5 1.3991(19) . ?
C32 C33 1.485(2) . ?
C3 C2 1.379(2) . ?
C23 C22 1.3792(19) . ?
C23 C24 1.4056(19) . ?
C22 C21 1.5001(19) . ?
C2 C1 1.4966(18) . ?
C10 C9 1.390(2) . ?
C10 C5 1.395(2) . ?
C9 C8 1.389(2) . ?
C15 C16 1.397(2) . ?
C15 C20 1.3981(19) . ?
C13 C12 1.379(2) . ?
C20 C19 1.392(2) . ?
C30 C25 1.394(2) . ?
C25 C26 1.393(2) . ?
C25 C24 1.4756(19) . ?
C8 C7 1.385(2) . ?
C12 C11 1.4946(19) . ?
C26 C27 1.390(2) . ?
C34 C35 1.345(2) . ?
C39 C38 1.386(2) . ?
C39 C37 1.387(2) 2_577 ?
C38 C37 1.389(2) . ?
C37 C39 1.387(2) 2_577 ?
