#------------------------------------------------------------------------------
#$Date: 2016-03-23 21:59:38 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179461 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/58/4335887.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_4335887
loop_
_publ_author_name
'Olga G. Tsay'
'Sudesh T. Manjare'
'Hyungjun Kim'
'Kang Mun Lee'
'Yoon Sup Lee'
'David G. Churchill'
_publ_section_title
;
 Novel Reversible Zn2+-Assisted Biological Phosphate "Turn-On" Probing
 through Stable Aryl-hydrazone Salicylaldimine Conjugation That Attenuates
 Ligand Hydrolysis
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              10052
_journal_page_last               10061
_journal_paper_doi               10.1021/ic4013526
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         C26H26B1Cl2F2N5O1
_chemical_formula_sum            'C26 H26 B Cl2 F2 N5 O'
_chemical_formula_weight         544.23
_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                 96.75(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.814(2)
_cell_length_b                   14.744(3)
_cell_length_c                   16.812(3)
_cell_measurement_reflns_used    6674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.55
_cell_measurement_theta_min      2.35
_cell_volume                     2662.0(9)
_computing_cell_refinement       'Bruker APEX II'
_computing_data_collection       'Bruker APEX II'
_computing_data_reduction        'Bruker APEX II'
_computing_molecular_graphics    ORTEP3
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0266
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            40476
_diffrn_reflns_theta_full        28.55
_diffrn_reflns_theta_max         28.55
_diffrn_reflns_theta_min         2.35
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Darkred
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         6674
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0490
_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)+(0.0705P)²+0.8083P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1622
_reflns_number_gt                4024
_reflns_number_total             6674
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic4013526_si_002.cif
_cod_data_source_block           nchu001-1
_cod_database_code               4335887
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
B B 0.3464(3) 0.7098(2) 0.59255(13) 0.0712(7) Uani 1 1 d . . .
F1 F 0.27760(18) 0.63818(12) 0.61813(9) 0.1084(6) Uani 1 1 d . . .
F2 F 0.41038(18) 0.75236(12) 0.65851(8) 0.1045(6) Uani 1 1 d . . .
N1 N 0.25974(18) 0.77737(13) 0.54343(9) 0.0656(5) Uani 1 1 d . . .
N2 N 0.43922(18) 0.67409(12) 0.53683(9) 0.0611(5) Uani 1 1 d . . .
N3 N 0.20417(15) 0.64701(11) 0.06685(9) 0.0554(4) Uani 1 1 d . . .
N4 N 0.13402(19) 0.58425(13) 0.02214(10) 0.0655(5) Uani 1 1 d . . .
H101 H 0.073(2) 0.5556(15) 0.0447(14) 0.068(7) Uiso 1 1 d . . .
N5 N 0.08807(15) 0.50085(11) -0.09162(9) 0.0527(4) Uani 1 1 d . . .
O O 0.34807(15) 0.79273(11) 0.08435(7) 0.0667(4) Uani 1 1 d . . .
H1 H 0.3035 0.7550 0.0592 0.100 Uiso 1 1 calc R . .
C1 C 0.1677(2) 0.82612(19) 0.57020(15) 0.0773(7) Uani 1 1 d . . .
C2 C 0.1083(3) 0.8771(2) 0.50759(17) 0.0841(7) Uani 1 1 d . . .
H2 H 0.0419 0.9164 0.5111 0.101 Uiso 1 1 calc R . .
C3 C 0.1638(2) 0.86019(17) 0.43923(14) 0.0703(6) Uani 1 1 d . . .
C4 C 0.2598(2) 0.79627(15) 0.46151(11) 0.0582(5) Uani 1 1 d . . .
C5 C 0.34472(18) 0.75249(13) 0.41799(10) 0.0519(5) Uani 1 1 d . . .
C6 C 0.43507(19) 0.69383(14) 0.45481(10) 0.0549(5) Uani 1 1 d . . .
C7 C 0.5340(2) 0.64558(16) 0.42495(12) 0.0617(5) Uani 1 1 d . . .
C8 C 0.5940(2) 0.59875(18) 0.48887(14) 0.0747(6) Uani 1 1 d . . .
H8 H 0.6628 0.5613 0.4873 0.090 Uiso 1 1 calc R . .
C9 C 0.5347(2) 0.61667(17) 0.55621(13) 0.0711(6) Uani 1 1 d . . .
C10 C 0.33796(17) 0.76615(13) 0.32924(10) 0.0490(4) Uani 1 1 d . . .
C11 C 0.26910(17) 0.70763(13) 0.27716(10) 0.0490(4) Uani 1 1 d . . .
H11 H 0.2218 0.6626 0.2978 0.059 Uiso 1 1 calc R . .
C12 C 0.26882(16) 0.71439(12) 0.19411(10) 0.0458(4) Uani 1 1 d . . .
C13 C 0.34015(17) 0.78291(13) 0.16387(10) 0.0485(4) Uani 1 1 d . . .
C14 C 0.4065(2) 0.84285(14) 0.21573(11) 0.0596(5) Uani 1 1 d . . .
H14 H 0.4525 0.8890 0.1955 0.072 Uiso 1 1 calc R . .
C15 C 0.4049(2) 0.83463(14) 0.29736(11) 0.0594(5) Uani 1 1 d . . .
H15 H 0.4495 0.8757 0.3316 0.071 Uiso 1 1 calc R . .
C16 C 0.19643(18) 0.64988(14) 0.14209(11) 0.0545(5) Uani 1 1 d . . .
H16 H 0.1434 0.6099 0.1641 0.065 Uiso 1 1 calc R . .
C17 C 0.15507(18) 0.56848(13) -0.05572(10) 0.0511(4) Uani 1 1 d . . .
C18 C 0.2397(2) 0.61892(16) -0.09438(12) 0.0650(6) Uani 1 1 d . . .
H18 H 0.2863 0.6650 -0.0676 0.078 Uiso 1 1 calc R . .
C19 C 0.2526(2) 0.59909(17) -0.17258(13) 0.0674(6) Uani 1 1 d . . .
H19 H 0.3062 0.6331 -0.2002 0.081 Uiso 1 1 calc R . .
C20 C 0.1858(2) 0.52838(16) -0.21016(13) 0.0651(6) Uani 1 1 d . . .
H20 H 0.1943 0.5129 -0.2629 0.078 Uiso 1 1 calc R . .
C21 C 0.10677(19) 0.48197(14) -0.16746(12) 0.0589(5) Uani 1 1 d . . .
H21 H 0.0626 0.4338 -0.1926 0.071 Uiso 1 1 calc R . .
C22 C 0.1263(3) 0.9035(2) 0.35926(17) 0.0924(8) Uani 1 1 d . . .
H22A H 0.0576 0.9439 0.3631 0.139 Uiso 1 1 calc R . .
H22B H 0.1019 0.8573 0.3203 0.139 Uiso 1 1 calc R . .
H22C H 0.1953 0.9370 0.3432 0.139 Uiso 1 1 calc R . .
C23 C 0.1372(3) 0.8205(2) 0.65432(16) 0.1034(11) Uani 1 1 d . . .
H23A H 0.1122 0.7598 0.6653 0.155 Uiso 1 1 calc R . .
H23B H 0.0705 0.8616 0.6613 0.155 Uiso 1 1 calc R . .
H23C H 0.2093 0.8365 0.6905 0.155 Uiso 1 1 calc R . .
C24 C 0.5724(2) 0.64468(18) 0.34266(14) 0.0752(6) Uani 1 1 d . . .
H24A H 0.6412 0.6038 0.3410 0.113 Uiso 1 1 calc R . .
H24B H 0.5970 0.7046 0.3287 0.113 Uiso 1 1 calc R . .
H24C H 0.5038 0.6250 0.3052 0.113 Uiso 1 1 calc R . .
C25 C 0.5665(3) 0.5803(2) 0.63958(15) 0.0945(9) Uani 1 1 d . . .
H25A H 0.6036 0.6276 0.6737 0.142 Uiso 1 1 calc R . .
H25B H 0.6242 0.5310 0.6386 0.142 Uiso 1 1 calc R . .
H25C H 0.4921 0.5592 0.6596 0.142 Uiso 1 1 calc R . .
C26 C 0.4868(3) 0.13136(19) 0.05516(16) 0.0888(8) Uani 1 1 d D . .
H26A H 0.4404 0.1784 0.0243 0.107 Uiso 1 1 calc R A 1
H26B H 0.5499 0.1082 0.0239 0.107 Uiso 1 1 calc R A 1
Cl1 Cl 0.5616(3) 0.17873(19) 0.1513(2) 0.0837(12) Uani 0.57(2) 1 d P B 1
Cl2 Cl 0.38793(9) 0.04494(6) 0.07586(5) 0.1091(3) Uani 1 1 d . B .
Cl1A Cl 0.5811(11) 0.1685(7) 0.1259(10) 0.160(3) Uani 0.43(2) 1 d PD B 2
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
F2 B F1 109.36(19)
F2 B N1 110.6(2)
F1 B N1 110.1(2)
F2 B N2 109.9(2)
F1 B N2 109.8(2)
N1 B N2 107.07(16)
C1 N1 C4 107.9(2)
C1 N1 B 126.37(19)
C4 N1 B 125.71(19)
C9 N2 C6 107.66(19)
C9 N2 B 127.08(18)
C6 N2 B 125.2(2)
C16 N3 N4 118.08(16)
N3 N4 C17 119.71(17)
C17 N5 C21 116.73(17)
N1 C1 C2 109.2(2)
N1 C1 C23 122.8(3)
C2 C1 C23 128.0(3)
C3 C2 C1 109.0(2)
C2 C3 C4 106.1(2)
C2 C3 C22 124.8(3)
C4 C3 C22 129.2(2)
C5 C4 N1 119.8(2)
C5 C4 C3 132.36(19)
N1 C4 C3 107.81(19)
C6 C5 C4 121.57(17)
C6 C5 C10 118.36(17)
C4 C5 C10 120.05(19)
C5 C6 N2 120.28(19)
C5 C6 C7 132.04(17)
N2 C6 C7 107.68(18)
C8 C7 C6 106.29(19)
C8 C7 C24 124.3(2)
C6 C7 C24 129.4(2)
C7 C8 C9 108.7(2)
N2 C9 C8 109.67(19)
N2 C9 C25 122.4(2)
C8 C9 C25 127.9(3)
C11 C10 C15 118.46(16)
C11 C10 C5 120.40(16)
C15 C10 C5 121.07(16)
C10 C11 C12 121.68(16)
C11 C12 C13 118.44(15)
C11 C12 C16 119.37(16)
C13 C12 C16 122.18(15)
O C13 C14 117.71(16)
O C13 C12 122.34(16)
C14 C13 C12 119.95(16)
C15 C14 C13 120.33(17)
C14 C15 C10 121.10(17)
N3 C16 C12 121.51(17)
N5 C17 N4 114.54(17)
N5 C17 C18 122.53(17)
N4 C17 C18 122.93(17)
C19 C18 C17 118.62(19)
C18 C19 C20 119.6(2)
C21 C20 C19 117.75(19)
N5 C21 C20 124.72(19)
Cl1A C26 Cl2 117.8(4)
Cl1A C26 Cl1 14.6(7)
Cl2 C26 Cl1 108.60(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B F2 1.386(3)
B F1 1.389(3)
B N1 1.540(4)
B N2 1.544(3)
N1 C1 1.348(3)
N1 C4 1.405(2)
N2 C9 1.345(3)
N2 C6 1.405(2)
N3 C16 1.278(2)
N3 N4 1.365(2)
N4 C17 1.375(2)
N5 C17 1.335(2)
N5 C21 1.343(2)
O C13 1.357(2)
C1 C2 1.388(4)
C1 C23 1.492(3)
C2 C3 1.380(3)
C3 C4 1.419(3)
C3 C22 1.501(4)
C4 C5 1.398(3)
C5 C6 1.394(3)
C5 C10 1.499(2)
C6 C7 1.424(3)
C7 C8 1.374(3)
C7 C24 1.491(3)
C8 C9 1.391(4)
C9 C25 1.502(3)
C10 C11 1.383(2)
C10 C15 1.386(3)
C11 C12 1.399(2)
C12 C13 1.402(3)
C12 C16 1.456(2)
C13 C14 1.382(3)
C14 C15 1.380(3)
C17 C18 1.398(3)
C18 C19 1.370(3)
C19 C20 1.379(3)
C20 C21 1.363(3)
C26 Cl1A 1.571(10)
C26 Cl2 1.725(3)
C26 Cl1 1.857(5)
