#------------------------------------------------------------------------------
#$Date: 2016-03-23 02:40:15 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179198 $
#$URL: svn://www.crystallography.net/cod/cif/4/31/36/4313691.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_4313691
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            'C37 H36 B N7 O2 Zn'
_chemical_formula_weight         686.91
_chemical_name_common            TpZn(3-hydroxy-1,2-dimethyl-4(1H)-pyridinone)
_chemical_name_systematic
;

  ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.944(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2147(14)
_cell_length_b                   11.0738(13)
_cell_length_c                   24.646(3)
_cell_measurement_reflns_used    4087
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.48
_cell_measurement_theta_min      2.49
_cell_volume                     3273.1(7)
_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 0.994
_diffrn_measured_fraction_theta_max 0.994
_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  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            27739
_diffrn_reflns_theta_full        27.54
_diffrn_reflns_theta_max         27.54
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1432
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.426
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         7497
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.671
_refine_ls_shift/su_mean         0.050
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0384P)²+1.4355P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0920
_reflns_number_gt                5819
_reflns_number_total             7497
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic026029g_3.cif
_cod_data_source_block           '[Zn(hydrotris()]'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_original_cell_volume        3273.0(7)
_cod_database_code               4313691
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.75608(2) 0.30750(2) 0.598702(10) 0.01617(8) Uani 1 1 d . . .
O2 O 0.63488(12) 0.18645(13) 0.56524(6) 0.0209(3) Uani 1 1 d . . .
N6 N 0.79776(14) 0.36217(15) 0.52379(7) 0.0168(4) Uani 1 1 d . . .
O1 O 0.78869(12) 0.18590(13) 0.65761(6) 0.0206(3) Uani 1 1 d . . .
C6 C 0.53830(18) 0.29577(19) 0.66907(9) 0.0187(4) Uani 1 1 d . . .
H6 H 0.6165 0.2846 0.6731 0.022 Uiso 1 1 calc R . .
N4 N 0.90526(14) 0.40911(15) 0.63505(7) 0.0168(4) Uani 1 1 d . . .
N5 N 0.82745(14) 0.48176(15) 0.52199(7) 0.0157(4) Uani 1 1 d . . .
C24 C 0.80963(16) 0.31379(19) 0.47528(8) 0.0166(4) Uani 1 1 d . . .
N1 N 0.68975(14) 0.55369(15) 0.57760(7) 0.0165(4) Uani 1 1 d . . .
C20 C 1.03290(17) 0.18277(19) 0.66093(9) 0.0197(5) Uani 1 1 d . . .
H20 H 1.0013 0.1937 0.6229 0.024 Uiso 1 1 calc R . .
N3 N 0.89379(14) 0.52933(15) 0.62244(7) 0.0164(4) Uani 1 1 d . . .
N2 N 0.65915(14) 0.45954(15) 0.60795(7) 0.0165(4) Uani 1 1 d . . .
C19 C 1.07434(18) 0.0710(2) 0.67926(10) 0.0235(5) Uani 1 1 d . . .
H19 H 1.0715 0.0058 0.6540 0.028 Uiso 1 1 calc R . .
C25 C 0.78867(17) 0.18523(19) 0.46240(9) 0.0185(4) Uani 1 1 d . . .
C31 C 0.72320(17) 0.09097(18) 0.64677(9) 0.0186(4) Uani 1 1 d . . .
C7 C 0.47746(19) 0.2196(2) 0.69679(9) 0.0219(5) Uani 1 1 d . . .
H7 H 0.5139 0.1561 0.7191 0.026 Uiso 1 1 calc R . .
C5 C 0.48654(17) 0.38805(19) 0.63554(8) 0.0169(4) Uani 1 1 d . . .
C11 C 0.98348(19) 0.72825(19) 0.65180(9) 0.0230(5) Uani 1 1 d . . .
H11A H 0.9991 0.7493 0.6154 0.035 Uiso 1 1 calc R . .
H11B H 1.0446 0.7567 0.6806 0.035 Uiso 1 1 calc R . .
H11C H 0.9137 0.7666 0.6567 0.035 Uiso 1 1 calc R . .
C4 C 0.54886(17) 0.47072(18) 0.60553(8) 0.0164(4) Uani 1 1 d . . .
C15 C 1.03654(17) 0.27982(19) 0.69716(9) 0.0172(4) Uani 1 1 d . . .
C12 C 0.97290(17) 0.59413(19) 0.65600(9) 0.0178(4) Uani 1 1 d . . .
C14 C 0.99336(17) 0.39904(19) 0.67644(8) 0.0154(4) Uani 1 1 d . . .
C22 C 0.85739(17) 0.50678(19) 0.47324(9) 0.0173(4) Uani 1 1 d . . .
C23 C 0.84588(17) 0.40237(19) 0.44227(9) 0.0183(4) Uani 1 1 d . . .
H23 H 0.8597 0.3925 0.4059 0.022 Uiso 1 1 calc R . .
C2 C 0.59926(17) 0.61880(18) 0.55462(9) 0.0177(4) Uani 1 1 d . . .
C26 C 0.73741(19) 0.1521(2) 0.40921(9) 0.0238(5) Uani 1 1 d . . .
H26 H 0.7168 0.2126 0.3818 0.029 Uiso 1 1 calc R . .
C13 C 1.03729(18) 0.51381(19) 0.69112(9) 0.0188(5) Uani 1 1 d . . .
H13 H 1.0990 0.5326 0.7196 0.023 Uiso 1 1 calc R . .
C30 C 0.81969(19) 0.0955(2) 0.50155(9) 0.0236(5) Uani 1 1 d . . .
H30 H 0.8556 0.1165 0.5380 0.028 Uiso 1 1 calc R . .
C37 C 0.63935(18) 0.09373(19) 0.59695(9) 0.0194(5) Uani 1 1 d . . .
C9 C 0.31124(19) 0.3285(2) 0.65922(9) 0.0243(5) Uani 1 1 d . . .
H9 H 0.2333 0.3407 0.6561 0.029 Uiso 1 1 calc R . .
C1 C 0.60479(19) 0.71928(19) 0.51500(9) 0.0235(5) Uani 1 1 d . . .
H1A H 0.6531 0.7835 0.5336 0.035 Uiso 1 1 calc R . .
H1B H 0.5297 0.7515 0.5018 0.035 Uiso 1 1 calc R . .
H1C H 0.6352 0.6890 0.4836 0.035 Uiso 1 1 calc R . .
C8 C 0.36360(19) 0.2361(2) 0.69204(9) 0.0243(5) Uani 1 1 d . . .
H8 H 0.3218 0.1843 0.7111 0.029 Uiso 1 1 calc R . .
C3 C 0.50813(18) 0.56956(18) 0.57226(9) 0.0189(5) Uani 1 1 d . . .
H3 H 0.4332 0.5971 0.5636 0.023 Uiso 1 1 calc R . .
C21 C 0.89708(18) 0.62901(19) 0.45937(9) 0.0197(5) Uani 1 1 d . . .
H21A H 0.8349 0.6864 0.4550 0.029 Uiso 1 1 calc R . .
H21B H 0.9255 0.6243 0.4248 0.029 Uiso 1 1 calc R . .
H21C H 0.9567 0.6563 0.4892 0.029 Uiso 1 1 calc R . .
N7 N 0.65967(16) -0.10394(16) 0.66844(8) 0.0233(4) Uani 1 1 d . . .
C16 C 1.08503(18) 0.2623(2) 0.75250(9) 0.0226(5) Uani 1 1 d . . .
H16 H 1.0902 0.3279 0.7777 0.027 Uiso 1 1 calc R . .
C32 C 0.73243(18) -0.00765(19) 0.68165(9) 0.0203(5) Uani 1 1 d . . .
C10 C 0.37159(18) 0.4030(2) 0.63095(9) 0.0215(5) Uani 1 1 d . . .
H10 H 0.3345 0.4653 0.6081 0.026 Uiso 1 1 calc R . .
C35 C 0.5793(2) -0.1007(2) 0.62285(10) 0.0259(5) Uani 1 1 d . . .
H35 H 0.5296 -0.1673 0.6153 0.031 Uiso 1 1 calc R . .
C36 C 0.56640(19) -0.0056(2) 0.58716(10) 0.0243(5) Uani 1 1 d . . .
H36 H 0.5081 -0.0063 0.5556 0.029 Uiso 1 1 calc R . .
C18 C 1.12009(19) 0.0543(2) 0.73469(10) 0.0271(5) Uani 1 1 d . . .
H18 H 1.1475 -0.0228 0.7476 0.033 Uiso 1 1 calc R . .
C33 C 0.8172(2) -0.0122(2) 0.73383(9) 0.0266(5) Uani 1 1 d . . .
H33A H 0.8629 0.0611 0.7370 0.040 Uiso 1 1 calc R . .
H33B H 0.8650 -0.0831 0.7333 0.040 Uiso 1 1 calc R . .
H33C H 0.7794 -0.0176 0.7654 0.040 Uiso 1 1 calc R . .
C28 C 0.7463(2) -0.0567(2) 0.43513(10) 0.0293(6) Uani 1 1 d . . .
H28 H 0.7314 -0.1392 0.4261 0.035 Uiso 1 1 calc R . .
C29 C 0.7985(2) -0.0248(2) 0.48787(10) 0.0293(6) Uani 1 1 d . . .
H29 H 0.8201 -0.0857 0.5150 0.035 Uiso 1 1 calc R . .
C17 C 1.1257(2) 0.1497(2) 0.77100(10) 0.0283(5) Uani 1 1 d . . .
H17 H 1.1577 0.1384 0.8089 0.034 Uiso 1 1 calc R . .
C27 C 0.7159(2) 0.0315(2) 0.39565(10) 0.0282(5) Uani 1 1 d . . .
H27 H 0.6803 0.0098 0.3593 0.034 Uiso 1 1 calc R . .
C34 C 0.6730(2) -0.2132(2) 0.70310(11) 0.0335(6) Uani 1 1 d . . .
H34A H 0.6151 -0.2719 0.6881 0.050 Uiso 1 1 calc R . .
H34B H 0.6662 -0.1918 0.7409 0.050 Uiso 1 1 calc R . .
H34C H 0.7466 -0.2486 0.7034 0.050 Uiso 1 1 calc R . .
B1 B 0.8117(2) 0.5673(2) 0.56953(10) 0.0174(5) Uani 1 1 d . . .
H37 H 0.8263(16) 0.6638(17) 0.5575(8) 0.007(5) 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
O1 Zn1 O2 83.04(6) . . ?
O1 Zn1 N2 120.65(6) . . ?
O2 Zn1 N2 100.91(6) . . ?
O1 Zn1 N6 143.13(7) . . ?
O2 Zn1 N6 96.44(6) . . ?
N2 Zn1 N6 95.76(7) . . ?
O1 Zn1 N4 90.78(6) . . ?
O2 Zn1 N4 169.81(6) . . ?
N2 Zn1 N4 89.20(7) . . ?
N6 Zn1 N4 83.64(7) . . ?
C37 O2 Zn1 109.48(13) . . ?
C24 N6 N5 106.36(16) . . ?
C24 N6 Zn1 138.98(15) . . ?
N5 N6 Zn1 114.59(12) . . ?
C31 O1 Zn1 111.52(13) . . ?
C7 C6 C5 121.0(2) . . ?
C14 N4 N3 106.66(16) . . ?
C14 N4 Zn1 139.17(14) . . ?
N3 N4 Zn1 111.52(12) . . ?
C22 N5 N6 110.12(16) . . ?
C22 N5 B1 129.95(17) . . ?
N6 N5 B1 119.59(16) . . ?
N6 C24 C23 109.73(19) . . ?
N6 C24 C25 122.33(19) . . ?
C23 C24 C25 127.92(19) . . ?
C2 N1 N2 110.33(17) . . ?
C2 N1 B1 128.70(17) . . ?
N2 N1 B1 120.76(16) . . ?
C19 C20 C15 121.1(2) . . ?
C12 N3 N4 110.30(17) . . ?
C12 N3 B1 130.20(18) . . ?
N4 N3 B1 118.61(17) . . ?
C4 N2 N1 106.25(16) . . ?
C4 N2 Zn1 130.69(14) . . ?
N1 N2 Zn1 109.41(12) . . ?
C20 C19 C18 119.7(2) . . ?
C30 C25 C26 118.8(2) . . ?
C30 C25 C24 122.0(2) . . ?
C26 C25 C24 119.19(19) . . ?
O1 C31 C32 122.0(2) . . ?
O1 C31 C37 117.49(19) . . ?
C32 C31 C37 120.5(2) . . ?
C8 C7 C6 120.1(2) . . ?
C6 C5 C10 118.2(2) . . ?
C6 C5 C4 122.33(19) . . ?
C10 C5 C4 119.46(19) . . ?
N2 C4 C3 109.86(18) . . ?
N2 C4 C5 121.94(18) . . ?
C3 C4 C5 128.19(19) . . ?
C20 C15 C16 118.4(2) . . ?
C20 C15 C14 120.18(19) . . ?
C16 C15 C14 121.4(2) . . ?
N3 C12 C13 107.33(19) . . ?
N3 C12 C11 123.06(19) . . ?
C13 C12 C11 129.6(2) . . ?
N4 C14 C13 109.53(18) . . ?
N4 C14 C15 121.36(18) . . ?
C13 C14 C15 128.91(19) . . ?
N5 C22 C23 107.73(18) . . ?
N5 C22 C21 122.85(19) . . ?
C23 C22 C21 129.41(19) . . ?
C22 C23 C24 106.05(19) . . ?
N1 C2 C3 107.54(18) . . ?
N1 C2 C1 122.54(19) . . ?
C3 C2 C1 129.8(2) . . ?
C27 C26 C25 120.7(2) . . ?
C12 C13 C14 106.16(19) . . ?
C29 C30 C25 120.4(2) . . ?
O2 C37 C36 124.6(2) . . ?
O2 C37 C31 118.42(19) . . ?
C36 C37 C31 117.0(2) . . ?
C10 C9 C8 120.4(2) . . ?
C9 C8 C7 119.5(2) . . ?
C2 C3 C4 105.94(19) . . ?
C35 N7 C32 120.63(19) . . ?
C35 N7 C34 119.3(2) . . ?
C32 N7 C34 120.0(2) . . ?
C17 C16 C15 120.4(2) . . ?
C31 C32 N7 119.3(2) . . ?
C31 C32 C33 121.7(2) . . ?
N7 C32 C33 119.06(19) . . ?
C9 C10 C5 120.9(2) . . ?
N7 C35 C36 122.4(2) . . ?
C35 C36 C37 120.1(2) . . ?
C17 C18 C19 119.9(2) . . ?
C27 C28 C29 119.9(2) . . ?
C28 C29 C30 120.4(2) . . ?
C18 C17 C16 120.3(2) . . ?
C28 C27 C26 119.8(2) . . ?
N3 B1 N5 108.57(17) . . ?
N3 B1 N1 110.57(17) . . ?
N5 B1 N1 107.37(17) . . ?
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
Zn1 O1 1.9647(14) . ?
Zn1 O2 2.0506(15) . ?
Zn1 N2 2.0955(17) . ?
Zn1 N6 2.0955(17) . ?
Zn1 N4 2.1839(18) . ?
O2 C37 1.285(3) . ?
N6 C24 1.343(3) . ?
N6 N5 1.376(2) . ?
O1 C31 1.317(2) . ?
C6 C7 1.387(3) . ?
C6 C5 1.389(3) . ?
N4 C14 1.339(3) . ?
N4 N3 1.368(2) . ?
N5 C22 1.349(3) . ?
N5 B1 1.547(3) . ?
C24 C23 1.399(3) . ?
C24 C25 1.470(3) . ?
N1 C2 1.351(3) . ?
N1 N2 1.376(2) . ?
N1 B1 1.547(3) . ?
C20 C19 1.380(3) . ?
C20 C15 1.392(3) . ?
N3 C12 1.352(3) . ?
N3 B1 1.545(3) . ?
N2 C4 1.343(3) . ?
C19 C18 1.387(3) . ?
C25 C30 1.387(3) . ?
C25 C26 1.391(3) . ?
C31 C32 1.381(3) . ?
C31 C37 1.442(3) . ?
C7 C8 1.385(3) . ?
C5 C10 1.397(3) . ?
C5 C4 1.476(3) . ?
C11 C12 1.496(3) . ?
C4 C3 1.401(3) . ?
C15 C16 1.394(3) . ?
C15 C14 1.476(3) . ?
C12 C13 1.379(3) . ?
C14 C13 1.400(3) . ?
C22 C23 1.378(3) . ?
C22 C21 1.499(3) . ?
C2 C3 1.382(3) . ?
C2 C1 1.490(3) . ?
C26 C27 1.390(3) . ?
C30 C29 1.386(3) . ?
C37 C36 1.407(3) . ?
C9 C10 1.380(3) . ?
C9 C8 1.383(3) . ?
N7 C35 1.345(3) . ?
N7 C32 1.387(3) . ?
N7 C34 1.472(3) . ?
C16 C17 1.387(3) . ?
C32 C33 1.491(3) . ?
C35 C36 1.362(3) . ?
C18 C17 1.378(3) . ?
C28 C27 1.378(3) . ?
C28 C29 1.380(3) . ?
