#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:40:15 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179198 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/36/4313689.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_4313689
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            'C35 H32 B N7 O2 Zn'
_chemical_formula_weight         658.86
_chemical_name_common            TpZn(2,3-dihydroxypyridine)
_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                111.3000(10)
_cell_angle_beta                 96.615(2)
_cell_angle_gamma                102.364(2)
_cell_formula_units_Z            2
_cell_length_a                   11.0865(10)
_cell_length_b                   12.2292(11)
_cell_length_c                   15.4690(14)
_cell_measurement_reflns_used    5765
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.51
_cell_volume                     1865.3(3)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.891
_diffrn_measured_fraction_theta_max 0.891
_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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10782
_diffrn_reflns_theta_full        27.51
_diffrn_reflns_theta_max         27.51
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.696
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.448
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         7642
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0603
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1201P)²+2.1198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1833
_refine_ls_wR_factor_ref         0.1933
_reflns_number_gt                6599
_reflns_number_total             7642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic026029g_1.cif
_cod_data_source_block
'[Zn(hydrotris(...)borate)(2,3-dihydroxypyridine)]'
_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               4313689
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
H36 H 0.590(4) 1.049(3) 1.060(3) 0.028(9) Uiso 1 1 d . . .
H35 H 0.318(4) 0.691(4) 0.500(3) 0.031(10) Uiso 1 1 d . . .
C17 C 0.5359(13) 1.4103(6) 0.8283(6) 0.129(5) Uani 1 1 d . . .
H17 H 0.4987 1.4737 0.8368 0.155 Uiso 1 1 calc R . .
C18 C 0.6406(14) 1.4311(6) 0.8816(6) 0.146(6) Uani 1 1 d . . .
H18 H 0.6759 1.5074 0.9311 0.175 Uiso 1 1 calc R . .
Zn1 Zn 0.59317(3) 0.91580(3) 0.74314(2) 0.02510(15) Uani 1 1 d . . .
O2 O 0.5512(2) 0.98793(19) 0.88781(15) 0.0230(4) Uani 1 1 d . . .
O1 O 0.7617(2) 0.9984(2) 0.81700(17) 0.0385(6) Uani 1 1 d . . .
N6 N 0.6374(3) 0.8138(3) 0.60120(19) 0.0332(7) Uani 1 1 d . . .
N2 N 0.4706(3) 0.7536(2) 0.72130(17) 0.0249(5) Uani 1 1 d . . .
N4 N 0.4774(3) 0.9744(3) 0.6686(2) 0.0349(7) Uani 1 1 d . . .
N1 N 0.3740(3) 0.7109(2) 0.6436(2) 0.0320(6) Uani 1 1 d . . .
N7 N 0.6673(3) 1.0620(2) 1.03976(18) 0.0254(6) Uani 1 1 d . . .
C5 C 0.5227(3) 0.7222(3) 0.8656(2) 0.0272(7) Uani 1 1 d . . .
N3 N 0.4025(3) 0.8837(3) 0.5860(2) 0.0364(7) Uani 1 1 d . . .
N5 N 0.5282(3) 0.7315(3) 0.54046(19) 0.0357(7) Uani 1 1 d . . .
C35 C 0.6580(3) 1.0286(3) 0.9449(2) 0.0239(6) Uani 1 1 d . . .
C24 C 0.7333(4) 0.7818(3) 0.5614(3) 0.0382(9) Uani 1 1 d . . .
C4 C 0.4336(3) 0.6989(3) 0.7780(2) 0.0258(6) Uani 1 1 d . . .
C6 C 0.6510(3) 0.7419(3) 0.8664(2) 0.0303(7) Uani 1 1 d . . .
H6 H 0.6794 0.7368 0.8112 0.036 Uiso 1 1 calc R . .
C3 C 0.3120(4) 0.6217(3) 0.7384(3) 0.0402(9) Uani 1 1 d . . .
H3 H 0.2640 0.5738 0.7639 0.048 Uiso 1 1 calc R . .
C31 C 0.7738(3) 1.0380(3) 0.9099(2) 0.0333(8) Uani 1 1 d . . .
C10 C 0.4811(4) 0.7272(3) 0.9478(3) 0.0389(9) Uani 1 1 d . . .
H10 H 0.3953 0.7119 0.9480 0.047 Uiso 1 1 calc R . .
C23 C 0.6847(5) 0.6786(3) 0.4758(3) 0.0460(10) Uani 1 1 d . . .
H23 H 0.7307 0.6384 0.4345 0.055 Uiso 1 1 calc R . .
C12 C 0.3487(4) 0.9333(4) 0.5319(3) 0.0450(10) Uani 1 1 d . . .
C34 C 0.7809(3) 1.1056(3) 1.1036(2) 0.0343(8) Uani 1 1 d . . .
H34 H 0.7828 1.1265 1.1680 0.041 Uiso 1 1 calc R . .
C7 C 0.7377(4) 0.7692(3) 0.9491(3) 0.0419(9) Uani 1 1 d . . .
H7 H 0.8235 0.7824 0.9491 0.050 Uiso 1 1 calc R . .
C22 C 0.5555(5) 0.6486(3) 0.4651(2) 0.0416(10) Uani 1 1 d . . .
C2 C 0.2772(4) 0.6309(3) 0.6530(3) 0.0442(10) Uani 1 1 d . . .
C14 C 0.4665(4) 1.0804(4) 0.6647(3) 0.0417(9) Uani 1 1 d . . .
C32 C 0.8865(4) 1.0844(4) 0.9747(3) 0.0456(10) Uani 1 1 d . . .
H32 H 0.9620 1.0939 0.9539 0.055 Uiso 1 1 calc R . .
C25 C 0.8652(5) 0.8532(4) 0.6034(3) 0.0480(11) Uani 1 1 d . . .
C33 C 0.8894(4) 1.1179(4) 1.0723(3) 0.0452(10) Uani 1 1 d . . .
H33 H 0.9665 1.1487 1.1154 0.054 Uiso 1 1 calc R . .
C21 C 0.4557(5) 0.5447(4) 0.3892(3) 0.0476(11) Uani 1 1 d . . .
H21A H 0.4060 0.4979 0.4173 0.071 Uiso 1 1 calc R . .
H21B H 0.4948 0.4935 0.3449 0.071 Uiso 1 1 calc R . .
H21C H 0.4022 0.5759 0.3565 0.071 Uiso 1 1 calc R . .
C13 C 0.3877(5) 1.0572(4) 0.5801(3) 0.0487(11) Uani 1 1 d . . .
H13 H 0.3657 1.1147 0.5600 0.058 Uiso 1 1 calc R . .
C15 C 0.5336(6) 1.2006(4) 0.7420(3) 0.0572(14) Uani 1 1 d . . .
C11 C 0.2641(5) 0.8595(5) 0.4380(3) 0.0606(14) Uani 1 1 d . . .
H11A H 0.3047 0.8043 0.3989 0.091 Uiso 1 1 calc R . .
H11B H 0.2455 0.9125 0.4084 0.091 Uiso 1 1 calc R . .
H11C H 0.1870 0.8138 0.4455 0.091 Uiso 1 1 calc R . .
B1 B 0.3987(5) 0.7478(4) 0.5601(3) 0.0384(10) Uani 1 1 d . . .
C8 C 0.6956(5) 0.7765(4) 1.0313(3) 0.0538(13) Uani 1 1 d . . .
H8 H 0.7532 0.7958 1.0869 0.065 Uiso 1 1 calc R . .
C9 C 0.5697(6) 0.7555(4) 1.0307(3) 0.0522(12) Uani 1 1 d . . .
H9 H 0.5421 0.7600 1.0861 0.063 Uiso 1 1 calc R . .
C20 C 0.6504(6) 1.2243(4) 0.7981(4) 0.0660(15) Uani 1 1 d . . .
H20 H 0.6918 1.1637 0.7898 0.079 Uiso 1 1 calc R . .
C1 C 0.1576(5) 0.5661(5) 0.5771(5) 0.089(2) Uani 1 1 d . . .
H1A H 0.1221 0.6253 0.5647 0.133 Uiso 1 1 calc R . .
H1B H 0.0980 0.5177 0.5984 0.133 Uiso 1 1 calc R . .
H1C H 0.1768 0.5142 0.5200 0.133 Uiso 1 1 calc R . .
C16 C 0.4737(8) 1.2951(5) 0.7566(4) 0.089(2) Uani 1 1 d . . .
H16 H 0.3952 1.2811 0.7196 0.107 Uiso 1 1 calc R . .
C28 C 1.1222(6) 0.9899(5) 0.6812(5) 0.094(3) Uani 1 1 d . . .
C30 C 0.9145(6) 0.9774(6) 0.6736(4) 0.0314(13) Uani 0.55 1 d P . .
C26 C 0.9761(7) 0.7970(7) 0.5929(6) 0.0435(16) Uani 0.55 1 d P . .
C29 C 1.0412(7) 1.0403(7) 0.7125(5) 0.0374(15) Uani 0.55 1 d P . .
C27 C 1.1036(7) 0.8617(7) 0.6324(6) 0.0462(17) Uani 0.55 1 d P . .
C19 C 0.7037(10) 1.3411(5) 0.8672(5) 0.109(3) Uani 1 1 d . . .
H19 H 0.7832 1.3599 0.9047 0.131 Uiso 1 1 calc R . .
C30B C 0.9087(7) 0.8786(8) 0.6845(5) 0.0315(16) Uani 0.45 1 d P . .
C26B C 0.9127(8) 0.8954(8) 0.5340(6) 0.0374(18) Uani 0.45 1 d P . .
C29B C 1.0350(7) 0.9548(9) 0.7192(6) 0.0389(19) Uani 0.45 1 d P . .
C27B C 1.0374(8) 0.9672(10) 0.5684(7) 0.045(2) Uani 0.45 1 d P . .
C39 C 0.1289(13) 0.3671(11) 0.8059(9) 0.073(3) Uani 0.50 1 d P . .
C37 C -0.0379(10) 0.4298(12) 0.7375(13) 0.088(4) Uani 0.50 1 d P . .
C38 C 0.0296(12) 0.3444(12) 0.7275(10) 0.080(4) Uani 0.50 1 d P . .
C40 C 0.1400(18) 0.4553(16) 0.8818(8) 0.103(5) Uani 0.50 1 d P . .
C36 C -0.0166(11) 0.5173(13) 0.8068(11) 0.069(3) Uani 0.50 1 d P . .
C41 C 0.044(3) 0.5401(13) 0.8719(16) 0.149(11) Uani 0.50 1 d P . .
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
C18 C17 C16 122.5(8) . . ?
C17 C18 C19 120.7(8) . . ?
O1 Zn1 N4 129.03(13) . . ?
O1 Zn1 N2 132.56(12) . . ?
N4 Zn1 N2 98.29(12) . . ?
O1 Zn1 O2 80.33(9) . . ?
N4 Zn1 O2 102.47(10) . . ?
N2 Zn1 O2 87.00(9) . . ?
O1 Zn1 N6 99.64(11) . . ?
N4 Zn1 N6 85.28(11) . . ?
N2 Zn1 N6 85.83(11) . . ?
O2 Zn1 N6 170.13(9) . . ?
C35 O2 Zn1 105.23(19) . . ?
C31 O1 Zn1 115.9(2) . . ?
C24 N6 N5 106.2(3) . . ?
C24 N6 Zn1 141.7(3) . . ?
N5 N6 Zn1 109.2(2) . . ?
C4 N2 N1 107.2(3) . . ?
C4 N2 Zn1 134.1(2) . . ?
N1 N2 Zn1 113.9(2) . . ?
C14 N4 N3 105.8(3) . . ?
C14 N4 Zn1 138.7(3) . . ?
N3 N4 Zn1 114.0(2) . . ?
C2 N1 N2 109.3(3) . . ?
C2 N1 B1 132.4(3) . . ?
N2 N1 B1 117.8(3) . . ?
C35 N7 C34 123.2(3) . . ?
C10 C5 C6 119.2(3) . . ?
C10 C5 C4 121.3(3) . . ?
C6 C5 C4 119.5(3) . . ?
C12 N3 N4 110.0(3) . . ?
C12 N3 B1 128.3(3) . . ?
N4 N3 B1 121.4(3) . . ?
C22 N5 N6 110.4(3) . . ?
C22 N5 B1 129.4(3) . . ?
N6 N5 B1 120.1(3) . . ?
O2 C35 N7 121.5(3) . . ?
O2 C35 C31 120.6(3) . . ?
N7 C35 C31 118.0(3) . . ?
N6 C24 C23 109.5(4) . . ?
N6 C24 C25 122.1(3) . . ?
C23 C24 C25 128.3(4) . . ?
N2 C4 C3 109.9(3) . . ?
N2 C4 C5 119.3(3) . . ?
C3 C4 C5 130.7(3) . . ?
C5 C6 C7 120.7(4) . . ?
C2 C3 C4 105.6(3) . . ?
O1 C31 C32 125.1(3) . . ?
O1 C31 C35 116.6(3) . . ?
C32 C31 C35 118.2(3) . . ?
C5 C10 C9 119.4(4) . . ?
C22 C23 C24 106.4(3) . . ?
N3 C12 C13 107.8(4) . . ?
N3 C12 C11 123.1(4) . . ?
C13 C12 C11 129.1(4) . . ?
C33 C34 N7 119.5(3) . . ?
C8 C7 C6 119.7(4) . . ?
N5 C22 C23 107.5(4) . . ?
N5 C22 C21 122.5(4) . . ?
C23 C22 C21 130.0(4) . . ?
N1 C2 C3 107.9(3) . . ?
N1 C2 C1 121.7(4) . . ?
C3 C2 C1 130.3(4) . . ?
N4 C14 C13 110.0(4) . . ?
N4 C14 C15 122.2(4) . . ?
C13 C14 C15 127.9(4) . . ?
C31 C32 C33 120.8(4) . . ?
C30B C25 C30 56.5(5) . . ?
C30B C25 C26B 131.7(7) . . ?
C30 C25 C26B 88.3(5) . . ?
C30B C25 C24 120.5(5) . . ?
C30 C25 C24 128.8(4) . . ?
C26B C25 C24 107.1(5) . . ?
C30B C25 C26 79.6(5) . . ?
C30 C25 C26 107.1(5) . . ?
C26B C25 C26 81.3(5) . . ?
C24 C25 C26 123.2(4) . . ?
C34 C33 C32 120.3(3) . . ?
C12 C13 C14 106.5(3) . . ?
C20 C15 C16 119.5(5) . . ?
C20 C15 C14 123.5(4) . . ?
C16 C15 C14 116.9(6) . . ?
N5 B1 N1 108.3(3) . . ?
N5 B1 N3 108.4(4) . . ?
N1 B1 N3 110.7(3) . . ?
C9 C8 C7 119.9(4) . . ?
C8 C9 C10 121.1(4) . . ?
C15 C20 C19 117.8(7) . . ?
C17 C16 C15 118.2(8) . . ?
C29 C28 C29B 50.8(6) . . ?
C29 C28 C27 126.1(6) . . ?
C29B C28 C27 82.6(6) . . ?
C29 C28 C27B 84.5(7) . . ?
C29B C28 C27B 102.5(7) . . ?
C27 C28 C27B 80.3(6) . . ?
C29 C30 C25 126.4(6) . . ?
C27 C26 C25 125.1(6) . . ?
C28 C29 C30 118.4(7) . . ?
C26 C27 C28 113.0(7) . . ?
C20 C19 C18 121.3(10) . . ?
C25 C30B C29B 115.6(7) . . ?
C27B C26B C25 111.4(7) . . ?
C28 C29B C30B 134.7(8) . . ?
C26B C27B C28 120.9(7) . . ?
C40 C39 C38 117.9(13) . . ?
C36 C37 C38 121.8(15) . . ?
C37 C38 C39 118.0(13) . . ?
C39 C40 C41 112.4(13) . . ?
C41 C36 C37 128(2) . . ?
C36 C41 C40 120.8(14) . . ?
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
C17 C18 1.262(16) . ?
C17 C16 1.401(11) . ?
C18 C19 1.392(14) . ?
Zn1 O1 1.918(2) . ?
Zn1 N4 2.035(3) . ?
Zn1 N2 2.037(3) . ?
Zn1 O2 2.232(2) . ?
Zn1 N6 2.267(3) . ?
O2 C35 1.271(4) . ?
O1 C31 1.319(4) . ?
N6 C24 1.348(5) . ?
N6 N5 1.375(4) . ?
N2 C4 1.333(4) . ?
N2 N1 1.369(3) . ?
N4 C14 1.350(4) . ?
N4 N3 1.373(4) . ?
N1 C2 1.348(5) . ?
N1 B1 1.549(6) . ?
N7 C35 1.357(4) . ?
N7 C34 1.374(4) . ?
C5 C10 1.387(5) . ?
C5 C6 1.389(5) . ?
C5 C4 1.478(4) . ?
N3 C12 1.355(5) . ?
N3 B1 1.551(5) . ?
N5 C22 1.354(4) . ?
N5 B1 1.540(6) . ?
C35 C31 1.448(5) . ?
C24 C23 1.402(5) . ?
C24 C25 1.464(6) . ?
C4 C3 1.389(5) . ?
C6 C7 1.393(5) . ?
C3 C2 1.385(6) . ?
C31 C32 1.373(5) . ?
C10 C9 1.404(6) . ?
C23 C22 1.374(7) . ?
C12 C13 1.365(7) . ?
C12 C11 1.475(6) . ?
C34 C33 1.347(6) . ?
C7 C8 1.384(7) . ?
C22 C21 1.494(6) . ?
C2 C1 1.509(5) . ?
C14 C13 1.384(6) . ?
C14 C15 1.481(6) . ?
C32 C33 1.408(6) . ?
C25 C30B 1.190(9) . ?
C25 C30 1.447(7) . ?
C25 C26B 1.453(9) . ?
C25 C26 1.530(8) . ?
C15 C20 1.382(8) . ?
C15 C16 1.414(6) . ?
C8 C9 1.362(7) . ?
C20 C19 1.384(7) . ?
C28 C29 1.242(10) . ?
C28 C29B 1.266(10) . ?
C28 C27 1.426(10) . ?
C28 C27B 1.778(13) . ?
C30 C29 1.390(9) . ?
C26 C27 1.403(10) . ?
C30B C29B 1.422(12) . ?
C26B C27B 1.391(13) . ?
C39 C40 1.243(18) . ?
C39 C38 1.441(16) . ?
C37 C36 1.162(19) . ?
C37 C38 1.385(16) . ?
C40 C41 1.66(3) . ?
C36 C41 1.05(3) . ?
