#------------------------------------------------------------------------------
#$Date: 2022-01-22 01:07:58 +0200 (Sat, 22 Jan 2022) $
#$Revision: 272194 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566094.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_1566094
loop_
_publ_author_name
'Jackl, Moritz K.'
'Seo, Hyeonglim'
'Karges, Johannes'
'Kalaj, Mark'
'Cohen, Seth M.'
_publ_section_title
;
 Salicylate Metal-Binding Isosteres as Fragments for Metalloenzyme
 Inhibition
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06011B
_journal_year                    2022
_chemical_formula_moiety
'C38 H32 B N7 O4 Zn, 0.375(C5 H12), 0.249(C3 H3)'
_chemical_formula_sum            'C40.62 H37.25 B N7 O4 Zn'
_chemical_formula_weight         763.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-06
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-10-22 deposited with the CCDC.	2022-01-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.912(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.6546(9)
_cell_length_b                   14.6697(11)
_cell_length_c                   21.3858(17)
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.459
_cell_measurement_theta_min      3.665
_cell_volume                     3621.5(5)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22461
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.578
_diffrn_reflns_theta_min         3.665
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.373
_exptl_absorpt_correction_T_max  0.5220
_exptl_absorpt_correction_T_min  0.3756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1101 before and 0.0621 after correction.
The Ratio of minimum to maximum transmission is 0.7195.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear pink'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    pink
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             1588
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     526
_refine_ls_number_reflns         6808
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0635P)²+0.6944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1168
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5929
_reflns_number_total             6808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06011b4.cif
_cod_data_source_block           cohen_mkj214_0m_a
_cod_database_code               1566094
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.780
_shelx_estimated_absorpt_t_min   0.734
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6S-C8S_$1 \\sim C7S_$1-C8S_$1 \\sim C6S_$1-C7S_$1 \\sim C6S_$1-C8S \\sim
C7S-C8S \\sim C6S-C7S
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2S) = Uanis(C5S)
Uanis(C3S) = Uanis(C4S)
4. Rigid body (RIGU) restrains
 C1S, C2S, C3S
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C8S, C7S, C6S, C8S, C7S, C6S
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C1S)=Sof(H1SA)=
 Sof(H1SB)=Sof(H1SC)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=Sof(H5SC)=Sof(C4S)=Sof(H4SA)=
 Sof(H4SB)=0.5*(1-FVAR(2))
 Sof(C8S)=Sof(H8S)=Sof(C7S)=Sof(H7S)=Sof(C6S)=Sof(H6S)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 B1(H1B)
6.b Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C2S(H2SA,H2SB), C4S(H4SA,H4SB)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C36(H36), C23(H23), C9(H9), C1(H1A), C16(H16), C29(H29), C30(H30),
 C13(H13), C26(H26), C19(H19), C12(H12), C22(H22), C33(H33), C11(H11), C20(H20),
  C10(H10), C31(H31), C3(H3), C21(H21), C32(H32), C2(H2), C8S(H8S), C7S(H7S),
 C6S(H6S)
6.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C38(H38A,H38B,H38C), C28(H28A,H28B,H28C), C1S(H1SA,H1SB,
 H1SC), C5S(H5SA,H5SB,H5SC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.25854(2) 0.81053(2) 0.41051(2) 0.02934(10) Uani 1 1 d . . . . .
O3 O 0.27534(12) 0.67935(9) 0.40628(7) 0.0328(3) Uani 1 1 d . . . . .
O1 O 0.36044(13) 0.35329(9) 0.39876(7) 0.0369(3) Uani 1 1 d . . . . .
O2 O 0.46867(13) 0.38562(10) 0.49249(8) 0.0388(3) Uani 1 1 d . . . . .
O4 O 0.26255(13) 0.72399(10) 0.30645(8) 0.0389(3) Uani 1 1 d . . . . .
N6 N 0.22519(14) 0.86007(11) 0.49775(8) 0.0314(3) Uani 1 1 d . . . . .
N5 N 0.14937(14) 0.97977(11) 0.37640(8) 0.0318(3) Uani 1 1 d . . . . .
N4 N 0.12760(13) 0.88875(11) 0.36510(8) 0.0307(3) Uani 1 1 d . . . . .
N2 N 0.38828(13) 0.90206(11) 0.40681(8) 0.0304(3) Uani 1 1 d . . . . .
N7 N 0.20361(13) 0.95238(11) 0.49325(8) 0.0308(3) Uani 1 1 d . . . . .
N3 N 0.35894(14) 0.98786(11) 0.42503(8) 0.0309(3) Uani 1 1 d . . . . .
N1 N 0.37839(14) 0.49846(11) 0.42710(8) 0.0331(3) Uani 1 1 d . . . . .
H1 H 0.398402 0.547840 0.449323 0.040 Uiso 1 1 calc R U . . .
C35 C 0.19380(16) 0.83210(14) 0.55242(10) 0.0313(4) Uani 1 1 d . . . . .
C24 C 0.00339(16) 0.79448(15) 0.28907(10) 0.0336(4) Uani 1 1 d . . . . .
C36 C 0.15240(16) 0.90667(14) 0.58361(10) 0.0332(4) Uani 1 1 d . . . . .
H36 H 0.124992 0.906043 0.623433 0.040 Uiso 1 1 calc R U . . .
C15 C 0.49695(16) 0.90736(14) 0.39261(9) 0.0313(4) Uani 1 1 d . . . . .
C14 C 0.55466(16) 0.82834(14) 0.36777(10) 0.0322(4) Uani 1 1 d . . . . .
C34 C 0.20613(17) 0.73738(14) 0.57532(10) 0.0331(4) Uani 1 1 d . . . . .
C25 C 0.05065(16) 0.88285(14) 0.31259(10) 0.0323(4) Uani 1 1 d . . . . .
C6 C 0.31076(16) 0.49734(14) 0.36832(10) 0.0320(4) Uani 1 1 d . . . . .
C23 C -0.03404(17) 0.78158(15) 0.22496(11) 0.0362(4) Uani 1 1 d . . . . .
H23 H -0.028837 0.830306 0.196219 0.043 Uiso 1 1 calc R U . . .
C4 C 0.30023(17) 0.40608(14) 0.35121(10) 0.0345(4) Uani 1 1 d . . . . .
C17 C 0.44880(17) 1.04546(14) 0.42291(10) 0.0331(4) Uani 1 1 d . . . . .
C7 C 0.26107(16) 0.56513(14) 0.32832(10) 0.0326(4) Uani 1 1 d . . . . .
C37 C 0.15936(16) 0.98119(14) 0.54495(10) 0.0324(4) Uani 1 1 d . . . . .
C9 C 0.53990(17) 0.74059(15) 0.38980(11) 0.0373(4) Uani 1 1 d . . . . .
H9 H 0.495317 0.730961 0.423210 0.045 Uiso 1 1 calc R U . . .
C1 C 0.20076(18) 0.53602(16) 0.27077(10) 0.0370(4) Uani 1 1 d . . . . .
H1A H 0.166234 0.580266 0.241636 0.044 Uiso 1 1 calc R U . . .
C16 C 0.53778(17) 0.99642(14) 0.40236(10) 0.0329(4) Uani 1 1 d . . . . .
H16 H 0.611835 1.018824 0.396122 0.040 Uiso 1 1 calc R U . . .
C29 C 0.28980(17) 0.67842(14) 0.55681(10) 0.0343(4) Uani 1 1 d . . . . .
H29 H 0.339205 0.698803 0.527852 0.041 Uiso 1 1 calc R U . . .
C30 C 0.30085(18) 0.59022(15) 0.58061(10) 0.0363(4) Uani 1 1 d . . . . .
H30 H 0.357777 0.550631 0.567818 0.044 Uiso 1 1 calc R U . . .
C13 C 0.62404(18) 0.84161(15) 0.32058(11) 0.0379(5) Uani 1 1 d . . . . .
H13 H 0.636537 0.901538 0.306100 0.045 Uiso 1 1 calc R U . . .
C26 C 0.02395(17) 0.97071(15) 0.28940(10) 0.0352(4) Uani 1 1 d . . . . .
H26 H -0.028088 0.986440 0.252815 0.042 Uiso 1 1 calc R U . . .
C19 C -0.00554(17) 0.72222(15) 0.33074(11) 0.0353(4) Uani 1 1 d . . . . .
H19 H 0.018170 0.730483 0.374675 0.042 Uiso 1 1 calc R U . . .
C12 C 0.67527(19) 0.76772(16) 0.29445(12) 0.0413(5) Uani 1 1 d . . . . .
H12 H 0.723015 0.777277 0.262447 0.050 Uiso 1 1 calc R U . . .
C5 C 0.40905(17) 0.41217(14) 0.44521(10) 0.0342(4) Uani 1 1 d . . . . .
C27 C 0.08851(17) 1.02991(14) 0.33044(10) 0.0341(4) Uani 1 1 d . . . . .
C18 C 0.44447(18) 1.14376(14) 0.44053(11) 0.0382(4) Uani 1 1 d . . . . .
H18A H 0.398534 1.177520 0.406279 0.057 Uiso 1 1 calc R U . . .
H18B H 0.523294 1.168497 0.447674 0.057 Uiso 1 1 calc R U . . .
H18C H 0.408720 1.149793 0.479208 0.057 Uiso 1 1 calc R U . . .
C8 C 0.26762(16) 0.66331(14) 0.34666(10) 0.0337(4) Uani 1 1 d . . . . .
C22 C -0.07887(18) 0.69822(16) 0.20268(11) 0.0395(5) Uani 1 1 d . . . . .
H22 H -0.105117 0.690382 0.158951 0.047 Uiso 1 1 calc R U . . .
C33 C 0.13538(19) 0.70551(15) 0.61789(11) 0.0384(5) Uani 1 1 d . . . . .
H33 H 0.078184 0.744681 0.630861 0.046 Uiso 1 1 calc R U . . .
C11 C 0.65658(19) 0.68035(15) 0.31511(12) 0.0403(5) Uani 1 1 d . . . . .
H11 H 0.689301 0.629592 0.296368 0.048 Uiso 1 1 calc R U . . .
C20 C -0.04874(18) 0.63859(15) 0.30837(11) 0.0390(5) Uani 1 1 d . . . . .
H20 H -0.053354 0.589529 0.336916 0.047 Uiso 1 1 calc R U . . .
C38 C 0.12684(18) 1.07866(14) 0.55484(11) 0.0379(4) Uani 1 1 d . . . . .
H38A H 0.195633 1.117353 0.555936 0.057 Uiso 1 1 calc R U . . .
H38B H 0.095505 1.084176 0.594909 0.057 Uiso 1 1 calc R U . . .
H38C H 0.068147 1.098066 0.520118 0.057 Uiso 1 1 calc R U . . .
C10 C 0.59005(19) 0.66709(16) 0.36317(12) 0.0415(5) Uani 1 1 d . . . . .
H10 H 0.578684 0.607172 0.378010 0.050 Uiso 1 1 calc R U . . .
C28 C 0.09904(19) 1.13149(15) 0.32721(11) 0.0392(5) Uani 1 1 d . . . . .
H28A H 0.089787 1.157973 0.368294 0.059 Uiso 1 1 calc R U . . .
H28B H 0.038743 1.155405 0.294912 0.059 Uiso 1 1 calc R U . . .
H28C H 0.175465 1.147573 0.316325 0.059 Uiso 1 1 calc R U . . .
C31 C 0.22916(19) 0.55959(15) 0.62301(11) 0.0408(5) Uani 1 1 d . . . . .
H31 H 0.236637 0.499167 0.639048 0.049 Uiso 1 1 calc R U . . .
C3 C 0.24064(19) 0.37626(15) 0.29531(11) 0.0394(5) Uani 1 1 d . . . . .
H3 H 0.234273 0.313414 0.284686 0.047 Uiso 1 1 calc R U . . .
C21 C -0.08538(18) 0.62631(16) 0.24422(12) 0.0409(5) Uani 1 1 d . . . . .
H21 H -0.114750 0.568919 0.228903 0.049 Uiso 1 1 calc R U . . .
C32 C 0.1468(2) 0.61775(16) 0.64171(11) 0.0420(5) Uani 1 1 d . . . . .
H32 H 0.097935 0.597399 0.670957 0.050 Uiso 1 1 calc R U . . .
C2 C 0.18979(19) 0.44427(16) 0.25490(11) 0.0391(5) Uani 1 1 d . . . . .
H2 H 0.146684 0.427388 0.215642 0.047 Uiso 1 1 calc R U . . .
B1 B 0.23277(18) 1.00864(15) 0.43635(11) 0.0313(4) Uani 1 1 d . . . . .
H1B H 0.223868 1.075191 0.444608 0.038 Uiso 1 1 calc R U . . .
C3S C 0.011(5) 0.460(3) 0.510(4) 0.049(4) Uani 0.375(4) 1 d . . P A -1
H3SA H -0.061370 0.423896 0.498758 0.059 Uiso 0.375(4) 1 calc R U P A -1
H3SB H 0.031146 0.457854 0.556479 0.059 Uiso 0.375(4) 1 calc R U P A -1
C2S C 0.112(4) 0.4152(19) 0.478(2) 0.054(3) Uani 0.375(4) 1 d . . P A -1
H2SA H 0.090755 0.414313 0.431320 0.065 Uiso 0.375(4) 1 calc R U P A -1
H2SB H 0.183917 0.451283 0.487990 0.065 Uiso 0.375(4) 1 calc R U P A -1
C1S C 0.1313(7) 0.3163(6) 0.5033(5) 0.061(2) Uani 0.375(4) 1 d . . P A -1
H1SA H 0.061799 0.279820 0.489935 0.091 Uiso 0.375(4) 1 calc R U P A -1
H1SB H 0.146642 0.317606 0.549503 0.091 Uiso 0.375(4) 1 calc R U P A -1
H1SC H 0.197598 0.289204 0.486515 0.091 Uiso 0.375(4) 1 calc R U P A -1
C8S C -0.0724(11) 0.4520(8) 0.5354(6) 0.064(4) Uani 0.249(8) 1 d D . P A 2
H8S H -0.121876 0.421078 0.560135 0.076 Uiso 0.249(8) 1 calc R U P A 2
C7S C 0.0156(16) 0.4059(14) 0.5111(9) 0.078(5) Uani 0.249(8) 1 d D . P A 2
H7S H 0.026804 0.342258 0.517606 0.093 Uiso 0.249(8) 1 calc R U P A 2
C6S C 0.0863(14) 0.4557(11) 0.4773(8) 0.071(4) Uani 0.249(8) 1 d D . P A 2
H6S H 0.148286 0.424935 0.461824 0.085 Uiso 0.249(8) 1 calc R U P A 2
C5S C -0.114(4) 0.6008(18) 0.512(2) 0.054(3) Uani 0.375(4) 1 d . . P A -1
H5SA H -0.124370 0.662959 0.495329 0.081 Uiso 0.375(4) 1 calc R U P A -1
H5SB H -0.101806 0.602718 0.558209 0.081 Uiso 0.375(4) 1 calc R U P A -1
H5SC H -0.183431 0.564734 0.497500 0.081 Uiso 0.375(4) 1 calc R U P A -1
C4S C -0.010(5) 0.558(3) 0.489(4) 0.049(4) Uani 0.375(4) 1 d . . P A -1
H4SA H 0.059558 0.594159 0.503863 0.059 Uiso 0.375(4) 1 calc R U P A -1
H4SB H -0.021183 0.559535 0.441891 0.059 Uiso 0.375(4) 1 calc R U P A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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
O3 Zn1 N6 114.83(7) . . ?
O3 Zn1 N4 127.50(6) . . ?
O3 Zn1 N2 125.03(6) . . ?
N4 Zn1 N6 90.60(7) . . ?
N2 Zn1 N6 92.05(7) . . ?
N2 Zn1 N4 96.97(7) . . ?
C8 O3 Zn1 103.54(12) . . ?
C5 O1 C4 107.12(16) . . ?
N7 N6 Zn1 109.53(12) . . ?
C35 N6 Zn1 141.41(14) . . ?
C35 N6 N7 107.06(16) . . ?
N4 N5 B1 119.22(16) . . ?
C27 N5 N4 109.63(17) . . ?
C27 N5 B1 131.14(18) . . ?
N5 N4 Zn1 110.74(12) . . ?
C25 N4 Zn1 137.01(14) . . ?
C25 N4 N5 107.23(16) . . ?
N3 N2 Zn1 112.25(12) . . ?
C15 N2 Zn1 140.90(14) . . ?
C15 N2 N3 106.85(16) . . ?
N6 N7 B1 121.43(16) . . ?
C37 N7 N6 109.69(17) . . ?
C37 N7 B1 128.85(17) . . ?
N2 N3 B1 120.11(16) . . ?
C17 N3 N2 109.81(16) . . ?
C17 N3 B1 129.60(17) . . ?
C6 N1 H1 125.0 . . ?
C5 N1 H1 125.0 . . ?
C5 N1 C6 109.97(17) . . ?
N6 C35 C36 109.29(18) . . ?
N6 C35 C34 123.65(19) . . ?
C36 C35 C34 127.03(19) . . ?
C23 C24 C25 120.6(2) . . ?
C23 C24 C19 118.9(2) . . ?
C19 C24 C25 120.5(2) . . ?
C35 C36 H36 126.8 . . ?
C37 C36 C35 106.32(18) . . ?
C37 C36 H36 126.8 . . ?
N2 C15 C14 121.75(18) . . ?
N2 C15 C16 109.42(18) . . ?
C16 C15 C14 128.76(18) . . ?
C9 C14 C15 121.45(19) . . ?
C9 C14 C13 119.1(2) . . ?
C13 C14 C15 119.39(19) . . ?
C29 C34 C35 121.88(19) . . ?
C33 C34 C35 119.68(19) . . ?
C33 C34 C29 118.4(2) . . ?
N4 C25 C24 121.32(18) . . ?
N4 C25 C26 109.13(18) . . ?
C26 C25 C24 129.49(19) . . ?
C4 C6 N1 105.58(18) . . ?
C7 C6 N1 133.40(19) . . ?
C7 C6 C4 120.99(19) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.6(2) . . ?
C22 C23 H23 119.7 . . ?
C6 C4 O1 109.09(18) . . ?
C3 C4 O1 127.27(19) . . ?
C3 C4 C6 123.6(2) . . ?
N3 C17 C16 107.70(18) . . ?
N3 C17 C18 122.82(18) . . ?
C16 C17 C18 129.48(19) . . ?
C6 C7 C1 116.18(19) . . ?
C6 C7 C8 121.92(19) . . ?
C1 C7 C8 121.86(19) . . ?
N7 C37 C36 107.65(18) . . ?
N7 C37 C38 123.05(19) . . ?
C36 C37 C38 129.3(2) . . ?
C14 C9 H9 119.9 . . ?
C10 C9 C14 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C7 C1 H1A 119.0 . . ?
C2 C1 C7 122.0(2) . . ?
C2 C1 H1A 119.0 . . ?
C15 C16 H16 126.9 . . ?
C17 C16 C15 106.22(17) . . ?
C17 C16 H16 126.9 . . ?
C34 C29 H29 119.9 . . ?
C30 C29 C34 120.3(2) . . ?
C30 C29 H29 119.9 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.4(2) . . ?
C31 C30 H30 119.8 . . ?
C14 C13 H13 119.8 . . ?
C14 C13 C12 120.5(2) . . ?
C12 C13 H13 119.8 . . ?
C25 C26 H26 126.9 . . ?
C27 C26 C25 106.17(19) . . ?
C27 C26 H26 126.9 . . ?
C24 C19 H19 119.8 . . ?
C20 C19 C24 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.9(2) . . ?
C11 C12 H12 120.0 . . ?
O2 C5 O1 122.18(19) . . ?
O2 C5 N1 129.6(2) . . ?
N1 C5 O1 108.24(17) . . ?
N5 C27 C26 107.82(18) . . ?
N5 C27 C28 122.6(2) . . ?
C26 C27 C28 129.6(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C8 C7 115.52(18) . . ?
O4 C8 O3 123.3(2) . . ?
O4 C8 C7 121.2(2) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 C23 120.1(2) . . ?
C21 C22 H22 120.0 . . ?
C34 C33 H33 119.4 . . ?
C32 C33 C34 121.2(2) . . ?
C32 C33 H33 119.4 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.8 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C31 H31 120.3 . . ?
C32 C31 C30 119.5(2) . . ?
C32 C31 H31 120.3 . . ?
C4 C3 H3 122.2 . . ?
C4 C3 C2 115.7(2) . . ?
C2 C3 H3 122.2 . . ?
C22 C21 C20 119.8(2) . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C33 C32 H32 119.9 . . ?
C31 C32 C33 120.2(2) . . ?
C31 C32 H32 119.9 . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
N5 B1 H1B 110.0 . . ?
N7 B1 N5 108.84(16) . . ?
N7 B1 N3 109.47(16) . . ?
N7 B1 H1B 110.0 . . ?
N3 B1 N5 108.38(16) . . ?
N3 B1 H1B 110.0 . . ?
H3SA C3S H3SB 108.1 . . ?
C2S C3S H3SA 109.5 . . ?
C2S C3S H3SB 109.5 . . ?
C4S C3S H3SA 109.5 . . ?
C4S C3S H3SB 109.5 . . ?
C4S C3S C2S 111(2) . . ?
C3S C2S H2SA 110.1 . . ?
C3S C2S H2SB 110.1 . . ?
H2SA C2S H2SB 108.4 . . ?
C1S C2S C3S 108(3) . . ?
C1S C2S H2SA 110.1 . . ?
C1S C2S H2SB 110.1 . . ?
C2S C1S H1SA 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
C2S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C7S C8S H8S 120.8 . . ?
C6S C8S H8S 120.8 3_566 . ?
C6S C8S C7S 118.4(12) 3_566 . ?
C8S C7S H7S 121.2 . . ?
C6S C7S C8S 117.6(16) . . ?
C6S C7S H7S 121.2 . . ?
C8S C6S H6S 118.0 3_566 . ?
C7S C6S H6S 118.0 . . ?
H5SA C5S H5SB 109.5 . . ?
H5SA C5S H5SC 109.5 . . ?
H5SB C5S H5SC 109.5 . . ?
C4S C5S H5SA 109.5 . . ?
C4S C5S H5SB 109.5 . . ?
C4S C5S H5SC 109.5 . . ?
C3S C4S H4SA 108.9 . . ?
C3S C4S H4SB 108.9 . . ?
C5S C4S C3S 113(2) . . ?
C5S C4S H4SA 108.9 . . ?
C5S C4S H4SB 108.9 . . ?
H4SA C4S H4SB 107.7 . . ?
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 O3 1.9376(14) . ?
Zn1 N6 2.0879(17) . ?
Zn1 N4 2.0446(16) . ?
Zn1 N2 2.0318(16) . ?
O3 C8 1.287(3) . ?
O1 C4 1.389(3) . ?
O1 C5 1.378(3) . ?
O2 C5 1.210(3) . ?
O4 C8 1.233(3) . ?
N6 N7 1.378(2) . ?
N6 C35 1.337(3) . ?
N5 N4 1.374(2) . ?
N5 C27 1.348(3) . ?
N5 B1 1.557(3) . ?
N4 C25 1.340(3) . ?
N2 N3 1.375(2) . ?
N2 C15 1.345(3) . ?
N7 C37 1.351(3) . ?
N7 B1 1.546(3) . ?
N3 C17 1.351(3) . ?
N3 B1 1.553(3) . ?
N1 H1 0.8800 . ?
N1 C6 1.389(3) . ?
N1 C5 1.357(3) . ?
C35 C36 1.401(3) . ?
C35 C34 1.474(3) . ?
C24 C25 1.470(3) . ?
C24 C23 1.393(3) . ?
C24 C19 1.398(3) . ?
C36 H36 0.9500 . ?
C36 C37 1.380(3) . ?
C15 C14 1.475(3) . ?
C15 C16 1.396(3) . ?
C14 C9 1.390(3) . ?
C14 C13 1.391(3) . ?
C34 C29 1.401(3) . ?
C34 C33 1.391(3) . ?
C25 C26 1.401(3) . ?
C6 C4 1.389(3) . ?
C6 C7 1.386(3) . ?
C23 H23 0.9500 . ?
C23 C22 1.388(3) . ?
C4 C3 1.369(3) . ?
C17 C16 1.383(3) . ?
C17 C18 1.493(3) . ?
C7 C1 1.398(3) . ?
C7 C8 1.492(3) . ?
C37 C38 1.502(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C1 H1A 0.9500 . ?
C1 C2 1.390(3) . ?
C16 H16 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.390(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.390(3) . ?
C13 H13 0.9500 . ?
C13 C12 1.391(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.382(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.383(3) . ?
C27 C28 1.498(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C22 H22 0.9500 . ?
C22 C21 1.388(4) . ?
C33 H33 0.9500 . ?
C33 C32 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.384(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(3) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C10 H10 0.9500 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C31 H31 0.9500 . ?
C31 C32 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.397(3) . ?
C21 H21 0.9500 . ?
C32 H32 0.9500 . ?
C2 H2 0.9500 . ?
B1 H1B 1.0000 . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C3S C2S 1.59(5) . ?
C3S C4S 1.519(11) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C2S C1S 1.56(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
C8S H8S 0.9500 . ?
C8S C7S 1.388(13) . ?
C8S C6S 1.386(12) 3_566 ?
C7S H7S 0.9500 . ?
C7S C6S 1.378(13) . ?
C6S H6S 0.9500 . ?
C5S H5SA 0.9800 . ?
C5S H5SB 0.9800 . ?
C5S H5SC 0.9800 . ?
C5S C4S 1.51(4) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn1 O3 C8 O4 6.2(2) . . . . ?
Zn1 O3 C8 C7 -171.78(13) . . . . ?
Zn1 N6 N7 C37 167.65(12) . . . . ?
Zn1 N6 N7 B1 -14.1(2) . . . . ?
Zn1 N6 C35 C36 -161.29(16) . . . . ?
Zn1 N6 C35 C34 20.6(3) . . . . ?
Zn1 N4 C25 C24 32.3(3) . . . . ?
Zn1 N4 C25 C26 -150.35(16) . . . . ?
Zn1 N2 N3 C17 178.80(13) . . . . ?
Zn1 N2 N3 B1 -8.4(2) . . . . ?
Zn1 N2 C15 C14 4.1(3) . . . . ?
Zn1 N2 C15 C16 -178.70(17) . . . . ?
O1 C4 C3 C2 -178.5(2) . . . . ?
N6 N7 C37 C36 0.2(2) . . . . ?
N6 N7 C37 C38 179.72(18) . . . . ?
N6 N7 B1 N5 68.9(2) . . . . ?
N6 N7 B1 N3 -49.4(2) . . . . ?
N6 C35 C36 C37 0.4(2) . . . . ?
N6 C35 C34 C29 26.0(3) . . . . ?
N6 C35 C34 C33 -155.8(2) . . . . ?
N5 N4 C25 C24 -176.54(17) . . . . ?
N5 N4 C25 C26 0.8(2) . . . . ?
N4 N5 C27 C26 1.4(2) . . . . ?
N4 N5 C27 C28 -176.27(17) . . . . ?
N4 N5 B1 N7 -44.1(2) . . . . ?
N4 N5 B1 N3 74.9(2) . . . . ?
N4 C25 C26 C27 0.0(2) . . . . ?
N2 N3 C17 C16 0.6(2) . . . . ?
N2 N3 C17 C18 -179.48(18) . . . . ?
N2 N3 B1 N5 -53.4(2) . . . . ?
N2 N3 B1 N7 65.2(2) . . . . ?
N2 C15 C14 C9 -38.3(3) . . . . ?
N2 C15 C14 C13 140.7(2) . . . . ?
N2 C15 C16 C17 -0.3(2) . . . . ?
N7 N6 C35 C36 -0.4(2) . . . . ?
N7 N6 C35 C34 -178.49(17) . . . . ?
N3 N2 C15 C14 -176.62(17) . . . . ?
N3 N2 C15 C16 0.6(2) . . . . ?
N3 C17 C16 C15 -0.2(2) . . . . ?
N1 C6 C4 O1 0.0(2) . . . . ?
N1 C6 C4 C3 -179.0(2) . . . . ?
N1 C6 C7 C1 177.9(2) . . . . ?
N1 C6 C7 C8 -4.4(3) . . . . ?
C35 N6 N7 C37 0.1(2) . . . . ?
C35 N6 N7 B1 178.34(16) . . . . ?
C35 C36 C37 N7 -0.4(2) . . . . ?
C35 C36 C37 C38 -179.9(2) . . . . ?
C35 C34 C29 C30 178.37(19) . . . . ?
C35 C34 C33 C32 -178.2(2) . . . . ?
C24 C25 C26 C27 177.1(2) . . . . ?
C24 C23 C22 C21 -0.8(3) . . . . ?
C24 C19 C20 C21 -1.0(3) . . . . ?
C36 C35 C34 C29 -151.8(2) . . . . ?
C36 C35 C34 C33 26.4(3) . . . . ?
C15 N2 N3 C17 -0.7(2) . . . . ?
C15 N2 N3 B1 172.03(17) . . . . ?
C15 C14 C9 C10 176.5(2) . . . . ?
C15 C14 C13 C12 -177.2(2) . . . . ?
C14 C15 C16 C17 176.7(2) . . . . ?
C14 C9 C10 C11 0.9(4) . . . . ?
C14 C13 C12 C11 0.5(4) . . . . ?
C34 C35 C36 C37 178.50(19) . . . . ?
C34 C29 C30 C31 0.0(3) . . . . ?
C34 C33 C32 C31 -0.4(4) . . . . ?
C25 C24 C23 C22 -179.89(18) . . . . ?
C25 C24 C19 C20 -179.17(19) . . . . ?
C25 C26 C27 N5 -0.9(2) . . . . ?
C25 C26 C27 C28 176.6(2) . . . . ?
C6 N1 C5 O1 -0.8(2) . . . . ?
C6 N1 C5 O2 178.7(2) . . . . ?
C6 C4 C3 C2 0.3(3) . . . . ?
C6 C7 C1 C2 0.9(3) . . . . ?
C6 C7 C8 O3 -28.3(3) . . . . ?
C6 C7 C8 O4 153.62(19) . . . . ?
C23 C24 C25 N4 -152.41(19) . . . . ?
C23 C24 C25 C26 30.8(3) . . . . ?
C23 C24 C19 C20 1.3(3) . . . . ?
C23 C22 C21 C20 1.1(3) . . . . ?
C4 O1 C5 O2 -178.75(19) . . . . ?
C4 O1 C5 N1 0.7(2) . . . . ?
C4 C6 C7 C1 0.1(3) . . . . ?
C4 C6 C7 C8 177.75(18) . . . . ?
C4 C3 C2 C1 0.7(3) . . . . ?
C17 N3 B1 N5 117.7(2) . . . . ?
C17 N3 B1 N7 -123.7(2) . . . . ?
C7 C6 C4 O1 178.33(17) . . . . ?
C7 C6 C4 C3 -0.7(3) . . . . ?
C7 C1 C2 C3 -1.3(3) . . . . ?
C37 N7 B1 N5 -113.3(2) . . . . ?
C37 N7 B1 N3 128.4(2) . . . . ?
C9 C14 C13 C12 1.9(3) . . . . ?
C1 C7 C8 O3 149.24(19) . . . . ?
C1 C7 C8 O4 -28.8(3) . . . . ?
C16 C15 C14 C9 145.0(2) . . . . ?
C16 C15 C14 C13 -35.9(3) . . . . ?
C29 C34 C33 C32 0.1(3) . . . . ?
C29 C30 C31 C32 -0.3(3) . . . . ?
C30 C31 C32 C33 0.5(4) . . . . ?
C13 C14 C9 C10 -2.6(3) . . . . ?
C13 C12 C11 C10 -2.1(4) . . . . ?
C19 C24 C25 N4 28.1(3) . . . . ?
C19 C24 C25 C26 -148.7(2) . . . . ?
C19 C24 C23 C22 -0.4(3) . . . . ?
C19 C20 C21 C22 -0.2(3) . . . . ?
C12 C11 C10 C9 1.4(4) . . . . ?
C5 O1 C4 C6 -0.4(2) . . . . ?
C5 O1 C4 C3 178.5(2) . . . . ?
C5 N1 C6 C4 0.5(2) . . . . ?
C5 N1 C6 C7 -177.6(2) . . . . ?
C27 N5 N4 Zn1 158.00(13) . . . . ?
C27 N5 N4 C25 -1.4(2) . . . . ?
C27 N5 B1 N7 134.7(2) . . . . ?
C27 N5 B1 N3 -106.3(2) . . . . ?
C18 C17 C16 C15 179.9(2) . . . . ?
C8 C7 C1 C2 -176.81(19) . . . . ?
C33 C34 C29 C30 0.2(3) . . . . ?
B1 N5 N4 Zn1 -22.9(2) . . . . ?
B1 N5 N4 C25 177.65(16) . . . . ?
B1 N5 C27 C26 -177.49(19) . . . . ?
B1 N5 C27 C28 4.8(3) . . . . ?
B1 N7 C37 C36 -177.89(18) . . . . ?
B1 N7 C37 C38 1.7(3) . . . . ?
B1 N3 C17 C16 -171.29(19) . . . . ?
B1 N3 C17 C18 8.7(3) . . . . ?
C2S C3S C4S C5S 174(8) . . . . ?
C8S C7S C6S C8S -2(3) . . . 3_566 ?
C6S C8S C7S C6S 2(3) 3_566 . . . ?
C4S C3S C2S C1S 178.2(19) . . . . ?
