#------------------------------------------------------------------------------
#$Date: 2022-01-22 01:07:58 +0200 (Sat, 22 Jan 2022) $
#$Revision: 272194 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566099.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_1566099
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 H34 B N9 O2 Zn'
_chemical_formula_sum            'C38 H34 B N9 O2 Zn'
_chemical_formula_weight         724.92
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc292q48
_audit_creation_date             2021-08-27
_audit_creation_method
;
Olex2 1.3-alpha
(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                 107.2460(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.7054(13)
_cell_length_b                   12.3535(7)
_cell_length_c                   25.1484(14)
_cell_measurement_reflns_used    9187
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.68
_cell_volume                     7330.2(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            45312
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.414
_diffrn_reflns_theta_min         1.696
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_current           50.0
_diffrn_source_power             2.5
_diffrn_source_type              'Bruker TXS'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_correction_T_min  0.4602
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0998 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.9377.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_description       block
_exptl_crystal_F_000             3008
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         7531
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0393
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0318P)²+19.5391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6487
_reflns_number_total             7531
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc06011b4.cif
_cod_data_source_block           monoc_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               1566099
_shelx_shelxl_version_number     2018/3
_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   0.932
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C01F, C01E, C018, C010, C016, C01D
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C01F \\sim C01E \\sim C018 \\sim C010 \\sim C016 \\sim C01D: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C016) = Uanis(C01F) = Uanis(C01D) = Uanis(C01E) = Uanis(C018) =
Uanis(C010)
4. Rigid body (RIGU) restrains
 C018, C010, C016, C01D, C01F, C01E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5.a Ternary CH refined with riding coordinates:
 B01A(H01A)
5.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00L(H00L), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00S(H00S), C00T(H00T), C00U(H00U), C00X(H00X), C00Y(H00Y), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C019(H019), C01B(H01B),
 C01D(H01D), C01E(H01E), C01F(H01F)
5.c Idealised Me refined as rotating group:
 C00V(H00A,H00B,H00C), C00W(H00D,H00E,H00G), C00Z(H00H,H00I,H00J), C01H(H01C,
 H01G,H01H)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.65488(2) 0.34841(2) 0.59540(2) 0.01892(8) Uani 1 1 d . . . . .
O1 O 0.62992(7) 0.38678(16) 0.68239(7) 0.0361(4) Uani 1 1 d . . . . .
O2 O 0.57506(8) 0.3678(2) 0.73868(8) 0.0581(7) Uani 1 1 d . . . . .
N1 N 0.63103(9) 0.02482(18) 0.60243(10) 0.0413(6) Uani 1 1 d . . . . .
N2 N 0.65034(8) 0.11508(17) 0.58713(9) 0.0315(5) Uani 1 1 d . . . . .
N3 N 0.63841(7) 0.20127(16) 0.61539(8) 0.0256(4) Uani 1 1 d . . . . .
N4 N 0.66495(7) 0.35133(14) 0.51526(7) 0.0187(4) Uani 1 1 d . . . . .
N5 N 0.69570(7) 0.44083(14) 0.50901(7) 0.0197(4) Uani 1 1 d . . . . .
N6 N 0.73259(7) 0.41406(15) 0.63149(7) 0.0207(4) Uani 1 1 d . . . . .
N7 N 0.74061(7) 0.50963(15) 0.60684(7) 0.0205(4) Uani 1 1 d . . . . .
N8 N 0.61017(7) 0.48970(14) 0.57172(7) 0.0183(4) Uani 1 1 d . . . . .
N9 N 0.64138(7) 0.56654(14) 0.55392(7) 0.0186(4) Uani 1 1 d . . . . .
C1 C 0.56334(11) 0.1471(3) 0.72065(12) 0.0491(3) Uani 1 1 d . U . . .
H01D H 0.548691 0.177791 0.748180 0.059 Uiso 1 1 calc R U . . .
C2 C 0.55644(10) 0.0358(3) 0.70920(12) 0.0491(3) Uani 1 1 d . U . . .
H01F H 0.536604 -0.006538 0.728865 0.059 Uiso 1 1 calc R U . . .
C3 C 0.57716(10) -0.0134(3) 0.67095(11) 0.0491(3) Uani 1 1 d . U . . .
H01E H 0.572649 -0.088945 0.663993 0.059 Uiso 1 1 calc R U . . .
C4 C 0.60546(10) 0.0521(3) 0.64224(12) 0.0491(3) Uani 1 1 d . U . . .
C5 C 0.61147(11) 0.1640(3) 0.65139(12) 0.0491(3) Uani 1 1 d . U . . .
C6 C 0.59141(10) 0.2137(3) 0.69223(12) 0.0491(3) Uani 1 1 d . U . . .
C7 C 0.60117(10) 0.3300(3) 0.70329(10) 0.0426(7) Uani 1 1 d . . . . .
C8 C 0.57829(14) 0.4838(4) 0.74722(13) 0.0683(12) Uani 1 1 d . . . . .
H01C H 0.564865 0.520631 0.711168 0.102 Uiso 1 1 calc R U . . .
H01G H 0.617669 0.504640 0.765706 0.102 Uiso 1 1 calc R U . . .
H01H H 0.554531 0.504748 0.770565 0.102 Uiso 1 1 calc R U . . .
C9 C 0.57511(9) 0.18869(18) 0.47489(9) 0.0225(4) Uani 1 1 d . . . . .
H00T H 0.565878 0.248540 0.494288 0.027 Uiso 1 1 calc R U . . .
C10 C 0.53863(9) 0.10101(18) 0.46170(10) 0.0273(5) Uani 1 1 d . . . . .
H011 H 0.504906 0.100497 0.472518 0.033 Uiso 1 1 calc R U . . .
C11 C 0.55135(10) 0.01395(19) 0.43270(11) 0.0328(6) Uani 1 1 d . . . . .
H012 H 0.526403 -0.046283 0.423548 0.039 Uiso 1 1 calc R U . . .
C12 C 0.60061(10) 0.0153(2) 0.41716(11) 0.0346(6) Uani 1 1 d . . . . .
H014 H 0.609213 -0.044003 0.397028 0.041 Uiso 1 1 calc R U . . .
C13 C 0.63747(10) 0.10234(19) 0.43070(9) 0.0273(5) Uani 1 1 d . . . . .
H00X H 0.671226 0.102172 0.419943 0.033 Uiso 1 1 calc R U . . .
C14 C 0.62531(9) 0.19027(17) 0.46004(8) 0.0204(4) Uani 1 1 d . . . . .
C15 C 0.66211(8) 0.28632(17) 0.47188(8) 0.0196(4) Uani 1 1 d . . . . .
C16 C 0.69280(9) 0.33200(18) 0.43864(9) 0.0236(5) Uani 1 1 d . . . . .
H00O H 0.698471 0.301714 0.405978 0.028 Uiso 1 1 calc R U . . .
C17 C 0.71303(9) 0.42952(19) 0.46290(9) 0.0227(4) Uani 1 1 d . . . . .
C18 C 0.74591(11) 0.5155(2) 0.44400(10) 0.0315(5) Uani 1 1 d . . . . .
H00D H 0.724494 0.583472 0.438343 0.047 Uiso 1 1 calc R U . . .
H00E H 0.752257 0.493252 0.408920 0.047 Uiso 1 1 calc R U . . .
H00G H 0.782494 0.526071 0.472360 0.047 Uiso 1 1 calc R U . . .
C19 C 0.76866(9) 0.2116(2) 0.69993(10) 0.0278(5) Uani 1 1 d . . . . .
H00R H 0.751440 0.198868 0.661343 0.033 Uiso 1 1 calc R U . . .
C20 C 0.78211(10) 0.1244(2) 0.73672(11) 0.0358(6) Uani 1 1 d . . . . .
H015 H 0.773575 0.052687 0.723263 0.043 Uiso 1 1 calc R U . . .
C21 C 0.80807(11) 0.1426(3) 0.79321(11) 0.0439(7) Uani 1 1 d . . . . .
H01B H 0.818670 0.083253 0.818164 0.053 Uiso 1 1 calc R U . . .
C22 C 0.81827(11) 0.2470(3) 0.81268(10) 0.0438(7) Uani 1 1 d . . . . .
H019 H 0.834919 0.259466 0.851375 0.053 Uiso 1 1 calc R U . . .
C23 C 0.80450(10) 0.3346(2) 0.77640(10) 0.0349(6) Uani 1 1 d . . . . .
H013 H 0.811549 0.406281 0.790379 0.042 Uiso 1 1 calc R U . . .
C24 C 0.78028(9) 0.3170(2) 0.71930(9) 0.0266(5) Uani 1 1 d . . . . .
C25 C 0.77262(9) 0.41026(19) 0.68131(9) 0.0236(5) Uani 1 1 d . . . . .
C26 C 0.80563(9) 0.5037(2) 0.68838(9) 0.0278(5) Uani 1 1 d . . . . .
H00Q H 0.836797 0.521617 0.719705 0.033 Uiso 1 1 calc R U . . .
C27 C 0.78421(9) 0.56493(19) 0.64110(9) 0.0246(5) Uani 1 1 d . . . . .
C28 C 0.80204(10) 0.6747(2) 0.62763(11) 0.0320(5) Uani 1 1 d . . . . .
H00H H 0.808217 0.673090 0.590902 0.048 Uiso 1 1 calc R U . . .
H00I H 0.837280 0.695614 0.655790 0.048 Uiso 1 1 calc R U . . .
H00J H 0.772313 0.727419 0.627376 0.048 Uiso 1 1 calc R U . . .
C29 C 0.51213(9) 0.36728(18) 0.58686(9) 0.0230(5) Uani 1 1 d . . . . .
H00L H 0.540475 0.325240 0.577986 0.028 Uiso 1 1 calc R U . . .
C30 C 0.46863(9) 0.31578(19) 0.60147(9) 0.0262(5) Uani 1 1 d . . . . .
H00S H 0.467994 0.239024 0.603496 0.031 Uiso 1 1 calc R U . . .
C31 C 0.42622(9) 0.3758(2) 0.61307(9) 0.0270(5) Uani 1 1 d . . . . .
H00U H 0.396707 0.340544 0.623464 0.032 Uiso 1 1 calc R U . . .
C32 C 0.42710(9) 0.4873(2) 0.60942(10) 0.0288(5) Uani 1 1 d . . . . .
H00Y H 0.397517 0.528794 0.616305 0.035 Uiso 1 1 calc R U . . .
C33 C 0.47100(9) 0.53878(18) 0.59575(9) 0.0245(5) Uani 1 1 d . . . . .
H00P H 0.471260 0.615546 0.593628 0.029 Uiso 1 1 calc R U . . .
C34 C 0.51472(8) 0.48000(17) 0.58507(8) 0.0188(4) Uani 1 1 d . . . . .
C35 C 0.56108(8) 0.53768(17) 0.57133(8) 0.0186(4) Uani 1 1 d . . . . .
C36 C 0.56175(9) 0.64548(18) 0.55468(9) 0.0217(4) Uani 1 1 d . . . . .
H00F H 0.532745 0.697760 0.551433 0.026 Uiso 1 1 calc R U . . .
C37 C 0.61263(9) 0.66105(17) 0.54394(8) 0.0211(4) Uani 1 1 d . . . . .
C38 C 0.63523(10) 0.76124(18) 0.52475(9) 0.0260(5) Uani 1 1 d . . . . .
H00A H 0.672099 0.779434 0.551049 0.039 Uiso 1 1 calc R U . . .
H00B H 0.608738 0.821179 0.522837 0.039 Uiso 1 1 calc R U . . .
H00C H 0.639669 0.748749 0.487784 0.039 Uiso 1 1 calc R U . . .
B1 B 0.70087(10) 0.5388(2) 0.54840(10) 0.0202(5) Uani 1 1 d . . . . .
H01A H 0.716355 0.602513 0.533179 0.024 Uiso 1 1 calc R U . . .
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
N3 Zn1 O1 80.03(8) . . ?
N3 Zn1 N4 110.75(8) . . ?
N3 Zn1 N6 119.71(7) . . ?
N3 Zn1 N8 136.60(7) . . ?
N4 Zn1 O1 165.92(7) . . ?
N6 Zn1 O1 88.79(6) . . ?
N6 Zn1 N4 93.24(7) . . ?
N6 Zn1 N8 98.38(7) . . ?
N8 Zn1 O1 80.86(6) . . ?
N8 Zn1 N4 85.06(7) . . ?
C7 O1 Zn1 126.57(19) . . ?
C7 O2 C8 115.5(3) . . ?
N2 N1 C4 106.8(2) . . ?
N1 N2 N3 110.9(2) . . ?
N2 N3 Zn1 119.88(14) . . ?
C5 N3 Zn1 131.9(2) . . ?
C5 N3 N2 108.0(2) . . ?
N5 N4 Zn1 110.45(12) . . ?
C15 N4 Zn1 141.04(15) . . ?
C15 N4 N5 106.61(17) . . ?
N4 N5 B1 119.94(16) . . ?
C17 N5 N4 109.84(17) . . ?
C17 N5 B1 129.91(18) . . ?
N7 N6 Zn1 112.62(12) . . ?
C25 N6 Zn1 137.47(15) . . ?
C25 N6 N7 106.55(17) . . ?
N6 N7 B1 119.46(17) . . ?
C27 N7 N6 109.98(17) . . ?
C27 N7 B1 130.55(19) . . ?
N9 N8 Zn1 111.98(12) . . ?
C35 N8 Zn1 141.29(14) . . ?
C35 N8 N9 106.47(16) . . ?
N8 N9 B1 120.76(17) . . ?
C37 N9 N8 109.97(17) . . ?
C37 N9 B1 129.26(18) . . ?
C2 C1 H01D 119.4 . . ?
C6 C1 H01D 119.4 . . ?
C6 C1 C2 121.2(3) . . ?
C1 C2 H01F 118.8 . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 H01F 118.8 . . ?
C2 C3 H01E 121.4 . . ?
C2 C3 C4 117.1(3) . . ?
C4 C3 H01E 121.4 . . ?
N1 C4 C3 129.8(3) . . ?
N1 C4 C5 108.2(2) . . ?
C5 C4 C3 122.0(3) . . ?
N3 C5 C4 105.9(3) . . ?
N3 C5 C6 133.6(3) . . ?
C4 C5 C6 120.5(3) . . ?
C1 C6 C5 116.8(3) . . ?
C1 C6 C7 123.8(3) . . ?
C5 C6 C7 119.4(2) . . ?
O1 C7 O2 123.0(3) . . ?
O1 C7 C6 124.3(3) . . ?
O2 C7 C6 112.7(3) . . ?
O2 C8 H01C 109.5 . . ?
O2 C8 H01G 109.5 . . ?
O2 C8 H01H 109.5 . . ?
H01C C8 H01G 109.5 . . ?
H01C C8 H01H 109.5 . . ?
H01G C8 H01H 109.5 . . ?
C10 C9 H00T 119.6 . . ?
C10 C9 C14 120.9(2) . . ?
C14 C9 H00T 119.6 . . ?
C9 C10 H011 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C11 C10 H011 120.0 . . ?
C10 C11 H012 120.2 . . ?
C12 C11 C10 119.6(2) . . ?
C12 C11 H012 120.2 . . ?
C11 C12 H014 119.7 . . ?
C11 C12 C13 120.6(2) . . ?
C13 C12 H014 119.7 . . ?
C12 C13 H00X 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H00X 119.8 . . ?
C9 C14 C15 120.11(19) . . ?
C13 C14 C9 118.5(2) . . ?
C13 C14 C15 121.2(2) . . ?
N4 C15 C14 121.90(19) . . ?
N4 C15 C16 109.70(19) . . ?
C16 C15 C14 127.95(19) . . ?
C15 C16 H00O 126.9 . . ?
C17 C16 C15 106.10(19) . . ?
C17 C16 H00O 126.9 . . ?
N5 C17 C16 107.70(19) . . ?
N5 C17 C18 122.4(2) . . ?
C16 C17 C18 129.8(2) . . ?
C17 C18 H00D 109.5 . . ?
C17 C18 H00E 109.5 . . ?
C17 C18 H00G 109.5 . . ?
H00D C18 H00E 109.5 . . ?
H00D C18 H00G 109.5 . . ?
H00E C18 H00G 109.5 . . ?
C20 C19 H00R 119.8 . . ?
C24 C19 H00R 119.8 . . ?
C24 C19 C20 120.5(2) . . ?
C19 C20 H015 120.0 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H015 120.0 . . ?
C20 C21 H01B 120.2 . . ?
C22 C21 C20 119.6(2) . . ?
C22 C21 H01B 120.2 . . ?
C21 C22 H019 119.6 . . ?
C21 C22 C23 120.8(2) . . ?
C23 C22 H019 119.6 . . ?
C22 C23 H013 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C24 C23 H013 120.0 . . ?
C19 C24 C23 119.1(2) . . ?
C19 C24 C25 122.1(2) . . ?
C23 C24 C25 118.6(2) . . ?
N6 C25 C24 123.2(2) . . ?
N6 C25 C26 109.3(2) . . ?
C26 C25 C24 127.4(2) . . ?
C25 C26 H00Q 126.7 . . ?
C27 C26 C25 106.52(19) . . ?
C27 C26 H00Q 126.7 . . ?
N7 C27 C26 107.7(2) . . ?
N7 C27 C28 123.2(2) . . ?
C26 C27 C28 129.1(2) . . ?
C27 C28 H00H 109.5 . . ?
C27 C28 H00I 109.5 . . ?
C27 C28 H00J 109.5 . . ?
H00H C28 H00I 109.5 . . ?
H00H C28 H00J 109.5 . . ?
H00I C28 H00J 109.5 . . ?
C30 C29 H00L 119.6 . . ?
C30 C29 C34 120.8(2) . . ?
C34 C29 H00L 119.6 . . ?
C29 C30 H00S 119.9 . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H00S 119.9 . . ?
C30 C31 H00U 120.2 . . ?
C32 C31 C30 119.5(2) . . ?
C32 C31 H00U 120.2 . . ?
C31 C32 H00Y 119.9 . . ?
C31 C32 C33 120.2(2) . . ?
C33 C32 H00Y 119.9 . . ?
C32 C33 H00P 119.4 . . ?
C32 C33 C34 121.2(2) . . ?
C34 C33 H00P 119.4 . . ?
C29 C34 C35 122.42(19) . . ?
C33 C34 C29 117.9(2) . . ?
C33 C34 C35 119.62(19) . . ?
N8 C35 C34 123.08(19) . . ?
N8 C35 C36 109.32(18) . . ?
C36 C35 C34 127.57(19) . . ?
C35 C36 H00F 126.7 . . ?
C37 C36 C35 106.54(19) . . ?
C37 C36 H00F 126.7 . . ?
N9 C37 C36 107.67(19) . . ?
N9 C37 C38 123.31(19) . . ?
C36 C37 C38 129.0(2) . . ?
C37 C38 H00A 109.5 . . ?
C37 C38 H00B 109.5 . . ?
C37 C38 H00C 109.5 . . ?
H00A C38 H00B 109.5 . . ?
H00A C38 H00C 109.5 . . ?
H00B C38 H00C 109.5 . . ?
N5 B1 N7 109.59(18) . . ?
N5 B1 N9 109.24(17) . . ?
N5 B1 H01A 109.8 . . ?
N7 B1 N9 108.46(17) . . ?
N7 B1 H01A 109.8 . . ?
N9 B1 H01A 109.8 . . ?
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 2.4880(17) . ?
Zn1 N3 1.9605(19) . ?
Zn1 N4 2.1029(17) . ?
Zn1 N6 2.0333(17) . ?
Zn1 N8 2.0570(17) . ?
O1 C7 1.223(3) . ?
O2 C7 1.329(3) . ?
O2 C8 1.448(5) . ?
N1 C4 1.375(4) . ?
N2 N1 1.314(3) . ?
N3 N2 1.360(3) . ?
N3 C5 1.353(3) . ?
N4 N5 1.377(2) . ?
N4 C15 1.340(3) . ?
N5 C17 1.357(3) . ?
N5 B1 1.545(3) . ?
N6 C25 1.347(3) . ?
N7 N6 1.375(2) . ?
N7 C27 1.349(3) . ?
N7 B1 1.549(3) . ?
N8 N9 1.379(2) . ?
N8 C35 1.347(3) . ?
N9 C37 1.351(3) . ?
N9 B1 1.555(3) . ?
C1 H01D 0.9500 . ?
C1 C2 1.404(5) . ?
C2 H01F 0.9500 . ?
C3 C2 1.360(5) . ?
C3 H01E 0.9500 . ?
C4 C3 1.402(4) . ?
C5 C4 1.402(5) . ?
C5 C6 1.407(5) . ?
C6 C1 1.401(4) . ?
C6 C7 1.470(5) . ?
C8 H01C 0.9800 . ?
C8 H01G 0.9800 . ?
C8 H01H 0.9800 . ?
C9 H00T 0.9500 . ?
C9 C10 1.385(3) . ?
C10 H011 0.9500 . ?
C10 C11 1.387(3) . ?
C11 H012 0.9500 . ?
C11 C12 1.384(4) . ?
C12 H014 0.9500 . ?
C13 C12 1.384(3) . ?
C13 H00X 0.9500 . ?
C14 C9 1.397(3) . ?
C14 C13 1.395(3) . ?
C14 C15 1.471(3) . ?
C15 C16 1.403(3) . ?
C16 H00O 0.9500 . ?
C17 C16 1.376(3) . ?
C17 C18 1.498(3) . ?
C18 H00D 0.9800 . ?
C18 H00E 0.9800 . ?
C18 H00G 0.9800 . ?
C19 H00R 0.9500 . ?
C19 C20 1.394(3) . ?
C20 H015 0.9500 . ?
C20 C21 1.393(4) . ?
C21 H01B 0.9500 . ?
C22 C21 1.376(4) . ?
C22 H019 0.9500 . ?
C23 C22 1.390(4) . ?
C23 H013 0.9500 . ?
C24 C19 1.390(4) . ?
C24 C23 1.399(3) . ?
C24 C25 1.473(3) . ?
C25 C26 1.394(3) . ?
C26 H00Q 0.9500 . ?
C27 C26 1.376(3) . ?
C27 C28 1.496(3) . ?
C28 H00H 0.9800 . ?
C28 H00I 0.9800 . ?
C28 H00J 0.9800 . ?
C29 H00L 0.9500 . ?
C29 C30 1.389(3) . ?
C30 H00S 0.9500 . ?
C30 C31 1.383(3) . ?
C31 H00U 0.9500 . ?
C31 C32 1.381(3) . ?
C32 H00Y 0.9500 . ?
C33 C32 1.386(3) . ?
C33 H00P 0.9500 . ?
C34 C29 1.395(3) . ?
C34 C33 1.392(3) . ?
C34 C35 1.474(3) . ?
C35 C36 1.398(3) . ?
C36 H00F 0.9500 . ?
C36 C37 1.375(3) . ?
C37 C38 1.495(3) . ?
C38 H00A 0.9800 . ?
C38 H00B 0.9800 . ?
C38 H00C 0.9800 . ?
B1 H01A 1.0000 . ?
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 O1 C7 O2 -158.58(17) . . . . ?
Zn1 O1 C7 C6 21.2(3) . . . . ?
Zn1 N3 N2 N1 -173.40(14) . . . . ?
Zn1 N3 C5 C4 171.78(16) . . . . ?
Zn1 N3 C5 C6 -9.0(4) . . . . ?
Zn1 N4 N5 C17 166.07(13) . . . . ?
Zn1 N4 N5 B1 -19.6(2) . . . . ?
Zn1 N4 C15 C14 27.7(3) . . . . ?
Zn1 N4 C15 C16 -159.47(17) . . . . ?
Zn1 N6 C25 C24 27.0(3) . . . . ?
Zn1 N6 C25 C26 -156.05(18) . . . . ?
Zn1 N8 N9 C37 -174.11(13) . . . . ?
Zn1 N8 N9 B1 5.3(2) . . . . ?
Zn1 N8 C35 C34 -9.9(3) . . . . ?
Zn1 N8 C35 C36 171.81(17) . . . . ?
N1 C4 C3 C2 179.1(2) . . . . ?
N2 N1 C4 C3 178.3(2) . . . . ?
N2 N1 C4 C5 -1.4(3) . . . . ?
N2 N3 C5 C4 -2.3(2) . . . . ?
N2 N3 C5 C6 176.9(3) . . . . ?
N3 N2 N1 C4 -0.1(2) . . . . ?
N3 C5 C4 N1 2.3(3) . . . . ?
N3 C5 C4 C3 -177.4(2) . . . . ?
N3 C5 C6 C1 177.9(3) . . . . ?
N3 C5 C6 C7 -2.7(4) . . . . ?
N4 N5 C17 C16 0.6(2) . . . . ?
N4 N5 C17 C18 178.02(19) . . . . ?
N4 N5 B1 N7 72.4(2) . . . . ?
N4 N5 B1 N9 -46.3(2) . . . . ?
N4 C15 C16 C17 -1.8(2) . . . . ?
N5 N4 C15 C14 -170.69(17) . . . . ?
N5 N4 C15 C16 2.1(2) . . . . ?
N5 C17 C16 C15 0.7(2) . . . . ?
N6 N7 C27 C26 1.1(2) . . . . ?
N6 N7 C27 C28 -177.0(2) . . . . ?
N6 N7 B1 N5 -48.5(2) . . . . ?
N6 N7 B1 N9 70.7(2) . . . . ?
N6 C25 C26 C27 0.1(3) . . . . ?
N7 N6 C25 C24 -176.45(19) . . . . ?
N7 N6 C25 C26 0.5(2) . . . . ?
N7 C27 C26 C25 -0.7(2) . . . . ?
N8 N9 C37 C36 -0.7(2) . . . . ?
N8 N9 C37 C38 179.20(18) . . . . ?
N8 N9 B1 N5 56.5(2) . . . . ?
N8 N9 B1 N7 -62.9(2) . . . . ?
N8 C35 C36 C37 1.1(2) . . . . ?
N9 N8 C35 C34 176.79(17) . . . . ?
N9 N8 C35 C36 -1.5(2) . . . . ?
C1 C6 C7 O1 173.2(2) . . . . ?
C1 C6 C7 O2 -7.1(3) . . . . ?
C4 C3 C2 C1 -0.9(4) . . . . ?
C4 C5 C6 C1 -2.9(4) . . . . ?
C4 C5 C6 C7 176.4(2) . . . . ?
C5 N3 N2 N1 1.6(2) . . . . ?
C5 C4 C3 C2 -1.2(4) . . . . ?
C5 C6 C1 C2 0.9(4) . . . . ?
C5 C6 C7 O1 -6.2(4) . . . . ?
C5 C6 C7 O2 173.6(2) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
C6 C5 C4 N1 -177.0(2) . . . . ?
C6 C5 C4 C3 3.2(4) . . . . ?
C7 C6 C1 C2 -178.4(2) . . . . ?
C8 O2 C7 O1 5.6(4) . . . . ?
C8 O2 C7 C6 -174.2(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C14 C13 C12 -0.5(3) . . . . ?
C9 C14 C15 N4 29.7(3) . . . . ?
C9 C14 C15 C16 -141.8(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C13 C14 C9 C10 1.1(3) . . . . ?
C13 C14 C15 N4 -154.7(2) . . . . ?
C13 C14 C15 C16 33.9(3) . . . . ?
C14 C9 C10 C11 -0.9(3) . . . . ?
C14 C13 C12 C11 -0.3(4) . . . . ?
C14 C15 C16 C17 170.5(2) . . . . ?
C15 N4 N5 C17 -1.7(2) . . . . ?
C15 N4 N5 B1 172.61(17) . . . . ?
C15 C14 C9 C10 176.91(19) . . . . ?
C15 C14 C13 C12 -176.3(2) . . . . ?
C17 N5 B1 N7 -114.5(2) . . . . ?
C17 N5 B1 N9 126.8(2) . . . . ?
C18 C17 C16 C15 -176.5(2) . . . . ?
C19 C20 C21 C22 2.5(4) . . . . ?
C19 C24 C23 C22 2.0(3) . . . . ?
C19 C24 C25 N6 31.6(3) . . . . ?
C19 C24 C25 C26 -144.8(2) . . . . ?
C23 C22 C21 C20 -1.9(4) . . . . ?
C23 C24 C19 C20 -1.4(3) . . . . ?
C23 C24 C25 N6 -153.9(2) . . . . ?
C23 C24 C25 C26 29.7(3) . . . . ?
C24 C19 C20 C21 -0.9(3) . . . . ?
C24 C23 C22 C21 -0.4(4) . . . . ?
C24 C25 C26 C27 176.9(2) . . . . ?
C25 C24 C19 C20 173.1(2) . . . . ?
C25 C24 C23 C22 -172.7(2) . . . . ?
C27 N7 N6 Zn1 162.07(14) . . . . ?
C27 N7 N6 C25 -1.0(2) . . . . ?
C27 N7 B1 N5 132.9(2) . . . . ?
C27 N7 B1 N9 -108.0(2) . . . . ?
C28 C27 C26 C25 177.2(2) . . . . ?
C29 C30 C31 C32 0.7(3) . . . . ?
C29 C34 C33 C32 1.9(3) . . . . ?
C29 C34 C35 N8 -15.3(3) . . . . ?
C29 C34 C35 C36 162.6(2) . . . . ?
C30 C31 C32 C33 -1.8(4) . . . . ?
C33 C34 C29 C30 -3.0(3) . . . . ?
C33 C34 C35 N8 165.92(19) . . . . ?
C33 C34 C35 C36 -16.1(3) . . . . ?
C34 C29 C30 C31 1.7(3) . . . . ?
C34 C33 C32 C31 0.4(3) . . . . ?
C34 C35 C36 C37 -177.10(19) . . . . ?
C35 N8 N9 C37 1.4(2) . . . . ?
C35 N8 N9 B1 -179.17(17) . . . . ?
C35 C34 C29 C30 178.22(19) . . . . ?
C35 C34 C33 C32 -179.3(2) . . . . ?
C35 C36 C37 N9 -0.2(2) . . . . ?
C35 C36 C37 C38 179.9(2) . . . . ?
C37 N9 B1 N5 -124.1(2) . . . . ?
C37 N9 B1 N7 116.5(2) . . . . ?
B1 N5 C17 C16 -172.99(19) . . . . ?
B1 N5 C17 C18 4.4(3) . . . . ?
B1 N7 N6 Zn1 -16.9(2) . . . . ?
B1 N7 N6 C25 -179.91(18) . . . . ?
B1 N7 C27 C26 179.8(2) . . . . ?
B1 N7 C27 C28 1.7(4) . . . . ?
B1 N9 C37 C36 179.89(19) . . . . ?
B1 N9 C37 C38 -0.2(3) . . . . ?
