# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_K0991
_database_code_depnum_ccdc_archive 'CCDC 2128270'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C19 H30 B2 F N O4'
_chemical_formula_moiety         'C19 H30 B2 F N O4'
_chemical_formula_weight         377.06
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

#------------------------------------------------
_cell_length_a                   6.5967(4)
_cell_length_b                   12.0859(6)
_cell_length_c                   14.3335(7)
_cell_angle_alpha                105.4260(10)
_cell_angle_beta                 97.8810(10)
_cell_angle_gamma                103.3220(10)
_cell_volume                     1047.70(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    8441
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.16

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.138
_exptl_crystal_size_mid          0.353
_exptl_crystal_size_max          0.439

_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6619
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            15994
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.508
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_full        25.021
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991


#==========================================================================
# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_reflns_number_total             3664
_reflns_number_gt                2901
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3664
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1080
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.2357P] where P=(Fo²+2Fc²)/3'

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
F F 0.0171 0.0103 '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'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
F1 F 1.0174(2) 0.32851(13) 0.35540(8) 0.0922(4) Uani 1 1 d . . . . .
O1 O 0.42353(17) 0.20237(9) 0.77492(9) 0.0493(3) Uani 1 1 d . . . . .
O2 O 0.68988(18) 0.12352(9) 0.72809(10) 0.0583(4) Uani 1 1 d . . . . .
O3 O 0.54587(15) 0.47107(8) 0.84003(7) 0.0338(2) Uani 1 1 d . . . . .
O4 O 0.89454(15) 0.55728(8) 0.84009(7) 0.0350(2) Uani 1 1 d . . . . .
N1 N 0.76774(18) 0.33980(10) 0.77399(8) 0.0328(3) Uani 1 1 d . . . . .
C2 C 0.3393(3) 0.07285(14) 0.74721(15) 0.0577(5) Uani 1 1 d . . . . .
C6 C 0.5336(4) -0.08768(16) 0.68423(18) 0.0780(6) Uani 1 1 d . . . . .
H6A H 0.598250 -0.118822 0.629800 0.117 Uiso 1 1 calc R U . A 1
H6B H 0.397019 -0.143436 0.678083 0.117 Uiso 1 1 calc R U . A 1
H6C H 0.626392 -0.077190 0.746486 0.117 Uiso 1 1 calc R U . A 1
C7 C 0.5745(2) 0.60018(12) 0.86456(10) 0.0341(3) Uani 1 1 d . . . . .
C8 C 0.8197(2) 0.65101(12) 0.90016(10) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.8968(3) 0.66070(14) 1.00771(11) 0.0442(4) Uani 1 1 d . . . . .
H9A H 0.834882 0.585541 1.018806 0.066 Uiso 1 1 calc R U . . .
H9B H 0.853716 0.724073 1.050435 0.066 Uiso 1 1 calc R U . . .
H9C H 1.050939 0.678663 1.022511 0.066 Uiso 1 1 calc R U . . .
C10 C 0.9160(3) 0.76737(13) 0.88096(13) 0.0464(4) Uani 1 1 d . . . . .
H10A H 0.882242 0.756476 0.810505 0.070 Uiso 1 1 calc R U . . .
H10B H 1.069520 0.790987 0.904059 0.070 Uiso 1 1 calc R U . . .
H10C H 0.857958 0.829086 0.916041 0.070 Uiso 1 1 calc R U . . .
C11 C 0.4888(3) 0.62294(15) 0.76940(12) 0.0510(4) Uani 1 1 d . . . . .
H11A H 0.573237 0.600696 0.720927 0.077 Uiso 1 1 calc R U . . .
H11B H 0.497015 0.707060 0.783002 0.077 Uiso 1 1 calc R U . . .
H11C H 0.341536 0.575565 0.743613 0.077 Uiso 1 1 calc R U . . .
C12 C 0.4489(3) 0.63746(14) 0.94248(13) 0.0477(4) Uani 1 1 d . . . . .
H12A H 0.478615 0.723827 0.964052 0.072 Uiso 1 1 calc R U . . .
H12B H 0.489817 0.610922 0.998620 0.072 Uiso 1 1 calc R U . . .
H12C H 0.297748 0.601503 0.914660 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9771(2) 0.34193(13) 0.74755(10) 0.0354(3) Uani 1 1 d . . . . .
H13A H 1.019602 0.273392 0.759197 0.042 Uiso 1 1 calc R U . . .
H13B H 1.082855 0.414654 0.791728 0.042 Uiso 1 1 calc R U . . .
C14 C 0.9818(2) 0.33819(12) 0.64170(10) 0.0346(3) Uani 1 1 d . . . . .
C15 C 0.8232(3) 0.36029(14) 0.58138(11) 0.0428(4) Uani 1 1 d . . . . .
H15 H 0.705209 0.377145 0.606135 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8353(3) 0.35800(16) 0.48504(12) 0.0542(5) Uani 1 1 d . . . . .
H16 H 0.727553 0.373551 0.444584 0.065 Uiso 1 1 calc R U . . .
C17 C 1.0061(3) 0.33283(16) 0.45062(12) 0.0580(5) Uani 1 1 d . . . . .
C18 C 1.1678(3) 0.31189(18) 0.50736(14) 0.0627(5) Uani 1 1 d . . . . .
H18 H 1.285309 0.295628 0.481793 0.075 Uiso 1 1 calc R U . . .
C19 C 1.1545(3) 0.31520(16) 0.60363(12) 0.0504(4) Uani 1 1 d . . . . .
H19 H 1.265142 0.301525 0.643857 0.061 Uiso 1 1 calc R U . . .
B1 B 0.6270(3) 0.22500(15) 0.75873(13) 0.0364(4) Uani 1 1 d . . . . .
B2 B 0.7333(2) 0.45311(14) 0.81719(11) 0.0299(3) Uani 1 1 d . . . . .
C1A C 0.5037(6) 0.0229(3) 0.6818(4) 0.0427(11) Uani 0.407(4) 1 d . . P B 1
C3A C 0.1288(9) 0.0235(5) 0.7163(8) 0.096(3) Uani 0.407(4) 1 d . . P B 1
H3A1 H 0.056418 0.060104 0.765268 0.144 Uiso 0.407(4) 1 calc R U P B 1
H3A2 H 0.096110 -0.061627 0.707393 0.144 Uiso 0.407(4) 1 calc R U P B 1
H3A3 H 0.081349 0.036128 0.653855 0.144 Uiso 0.407(4) 1 calc R U P B 1
C4A C 0.4159(13) 0.0499(5) 0.8537(4) 0.098(3) Uani 0.407(4) 1 d . . P B 1
H4AA H 0.376815 -0.035272 0.844784 0.146 Uiso 0.407(4) 1 calc R U P B 1
H4AB H 0.346455 0.089042 0.902831 0.146 Uiso 0.407(4) 1 calc R U P B 1
H4AC H 0.569222 0.082439 0.875842 0.146 Uiso 0.407(4) 1 calc R U P B 1
C5A C 0.4098(11) 0.0029(5) 0.5752(4) 0.091(2) Uani 0.407(4) 1 d . . P B 1
H5AA H 0.517139 -0.006920 0.536144 0.136 Uiso 0.407(4) 1 calc R U P B 1
H5AB H 0.361698 0.071216 0.569190 0.136 Uiso 0.407(4) 1 calc R U P B 1
H5AC H 0.289995 -0.068479 0.551392 0.136 Uiso 0.407(4) 1 calc R U P B 1
C1B C 0.5271(4) 0.0296(2) 0.7543(3) 0.0459(8) Uani 0.593(4) 1 d . . P B 2
C3B C 0.1999(6) 0.0410(3) 0.6396(3) 0.0712(12) Uani 0.593(4) 1 d . . P B 2
H3BA H 0.291298 0.061968 0.595777 0.107 Uiso 0.593(4) 1 calc R U P B 2
H3BB H 0.094759 0.085618 0.642086 0.107 Uiso 0.593(4) 1 calc R U P B 2
H3BC H 0.128061 -0.043933 0.615073 0.107 Uiso 0.593(4) 1 calc R U P B 2
C4B C 0.1757(6) 0.0436(3) 0.8122(4) 0.0675(11) Uani 0.593(4) 1 d . . P B 2
H4BA H 0.057075 0.075556 0.797824 0.101 Uiso 0.593(4) 1 calc R U P B 2
H4BB H 0.244526 0.079488 0.881615 0.101 Uiso 0.593(4) 1 calc R U P B 2
H4BC H 0.123758 -0.042337 0.797439 0.101 Uiso 0.593(4) 1 calc R U P B 2
C5B C 0.6055(5) 0.0267(3) 0.8582(2) 0.0577(9) Uani 0.593(4) 1 d . . P B 2
H5BA H 0.507958 -0.038088 0.871271 0.087 Uiso 0.593(4) 1 calc R U P B 2
H5BB H 0.612219 0.102017 0.906010 0.087 Uiso 0.593(4) 1 calc R U P B 2
H5BC H 0.746248 0.014361 0.863677 0.087 Uiso 0.593(4) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
F1 C17 1.3649(19) . ?
O1 B1 1.371(2) . ?
O1 C2 1.4576(18) . ?
O2 B1 1.366(2) . ?
O2 C1A 1.445(4) . ?
O2 C1B 1.536(3) . ?
O3 B2 1.3713(18) . ?
O3 C7 1.4656(16) . ?
O4 B2 1.3751(18) . ?
O4 C8 1.4574(16) . ?
N1 B1 1.423(2) . ?
N1 B2 1.4287(19) . ?
N1 C13 1.4778(18) . ?
C2 C3A 1.338(6) . ?
C2 C1B 1.453(3) . ?
C2 C4B 1.559(4) . ?
C2 C3B 1.583(4) . ?
C2 C1A 1.642(5) . ?
C2 C4A 1.655(7) . ?
C6 C1A 1.404(4) . ?
C6 C1B 1.517(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C7 C12 1.515(2) . ?
C7 C11 1.522(2) . ?
C7 C8 1.550(2) . ?
C8 C10 1.516(2) . ?
C8 C9 1.520(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
C13 C14 1.511(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C19 1.382(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.387(2) . ?
C15 H15 0.9400 . ?
C16 C17 1.354(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.364(3) . ?
C18 C19 1.385(2) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
C1A C5A 1.501(8) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C3A H3A3 0.9700 . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A H4AC 0.9700 . ?
C5A H5AA 0.9700 . ?
C5A H5AB 0.9700 . ?
C5A H5AC 0.9700 . ?
C1B C5B 1.520(5) . ?
C3B H3BA 0.9700 . ?
C3B H3BB 0.9700 . ?
C3B H3BC 0.9700 . ?
C4B H4BA 0.9700 . ?
C4B H4BB 0.9700 . ?
C4B H4BC 0.9700 . ?
C5B H5BA 0.9700 . ?
C5B H5BB 0.9700 . ?
C5B H5BC 0.9700 . ?

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
B1 O1 C2 106.70(12) . . ?
B1 O2 C1A 109.16(18) . . ?
B1 O2 C1B 103.54(15) . . ?
B2 O3 C7 105.88(10) . . ?
B2 O4 C8 106.19(10) . . ?
B1 N1 B2 127.04(13) . . ?
B1 N1 C13 116.34(12) . . ?
B2 N1 C13 116.52(11) . . ?
C3A C2 O1 119.1(3) . . ?
C1B C2 O1 104.56(16) . . ?
C1B C2 C4B 118.8(2) . . ?
O1 C2 C4B 108.21(18) . . ?
C1B C2 C3B 116.5(2) . . ?
O1 C2 C3B 102.36(18) . . ?
C4B C2 C3B 105.0(3) . . ?
C3A C2 C1A 120.2(4) . . ?
O1 C2 C1A 103.59(18) . . ?
C3A C2 C4A 108.4(5) . . ?
O1 C2 C4A 100.6(2) . . ?
C1A C2 C4A 101.9(4) . . ?
C1A C6 H6A 109.5 . . ?
C1A C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1A C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C12 108.99(11) . . ?
O3 C7 C11 106.60(11) . . ?
C12 C7 C11 110.46(13) . . ?
O3 C7 C8 102.08(10) . . ?
C12 C7 C8 114.60(12) . . ?
C11 C7 C8 113.39(12) . . ?
O4 C8 C10 108.57(11) . . ?
O4 C8 C9 106.86(11) . . ?
C10 C8 C9 110.35(12) . . ?
O4 C8 C7 101.91(10) . . ?
C10 C8 C7 115.40(12) . . ?
C9 C8 C7 112.99(12) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 114.48(11) . . ?
N1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N1 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C19 C14 C15 118.05(14) . . ?
C19 C14 C13 118.94(13) . . ?
C15 C14 C13 122.98(13) . . ?
C14 C15 C16 121.18(16) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 118.47(17) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?
C16 C17 C18 122.67(16) . . ?
C16 C17 F1 118.81(18) . . ?
C18 C17 F1 118.52(18) . . ?
C17 C18 C19 118.30(17) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C14 C19 C18 121.32(17) . . ?
C14 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
O2 B1 O1 112.82(13) . . ?
O2 B1 N1 121.18(14) . . ?
O1 B1 N1 125.98(14) . . ?
O3 B2 O4 113.42(12) . . ?
O3 B2 N1 125.67(13) . . ?
O4 B2 N1 120.91(13) . . ?
C6 C1A O2 114.3(3) . . ?
C6 C1A C5A 104.5(4) . . ?
O2 C1A C5A 116.7(4) . . ?
C6 C1A C2 116.9(3) . . ?
O2 C1A C2 97.6(2) . . ?
C5A C1A C2 107.1(4) . . ?
C2 C3A H3A1 109.5 . . ?
C2 C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2 C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C2 C4A H4AA 109.5 . . ?
C2 C4A H4AB 109.5 . . ?
H4AA C4A H4AB 109.5 . . ?
C2 C4A H4AC 109.5 . . ?
H4AA C4A H4AC 109.5 . . ?
H4AB C4A H4AC 109.5 . . ?
C1A C5A H5AA 109.5 . . ?
C1A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
C1A C5A H5AC 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
C2 C1B C6 122.1(3) . . ?
C2 C1B C5B 112.1(3) . . ?
C6 C1B C5B 106.1(2) . . ?
C2 C1B O2 102.14(19) . . ?
C6 C1B O2 103.2(2) . . ?
C5B C1B O2 110.5(2) . . ?
C2 C3B H3BA 109.5 . . ?
C2 C3B H3BB 109.5 . . ?
H3BA C3B H3BB 109.5 . . ?
C2 C3B H3BC 109.5 . . ?
H3BA C3B H3BC 109.5 . . ?
H3BB C3B H3BC 109.5 . . ?
C2 C4B H4BA 109.5 . . ?
C2 C4B H4BB 109.5 . . ?
H4BA C4B H4BB 109.5 . . ?
C2 C4B H4BC 109.5 . . ?
H4BA C4B H4BC 109.5 . . ?
H4BB C4B H4BC 109.5 . . ?
C1B C5B H5BA 109.5 . . ?
C1B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
C1B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?

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
B1 O1 C2 C3A -152.6(5) . . . . ?
B1 O1 C2 C1B 22.6(2) . . . . ?
B1 O1 C2 C4B 150.2(2) . . . . ?
B1 O1 C2 C3B -99.3(2) . . . . ?
B1 O1 C2 C1A -15.9(2) . . . . ?
B1 O1 C2 C4A 89.2(3) . . . . ?
B2 O3 C7 C12 -147.64(12) . . . . ?
B2 O3 C7 C11 93.13(13) . . . . ?
B2 O3 C7 C8 -26.05(13) . . . . ?
B2 O4 C8 C10 -148.75(12) . . . . ?
B2 O4 C8 C9 92.23(13) . . . . ?
B2 O4 C8 C7 -26.52(13) . . . . ?
O3 C7 C8 O4 31.88(12) . . . . ?
C12 C7 C8 O4 149.52(12) . . . . ?
C11 C7 C8 O4 -82.38(13) . . . . ?
O3 C7 C8 C10 149.29(12) . . . . ?
C12 C7 C8 C10 -93.07(15) . . . . ?
C11 C7 C8 C10 35.03(17) . . . . ?
O3 C7 C8 C9 -82.42(13) . . . . ?
C12 C7 C8 C9 35.22(17) . . . . ?
C11 C7 C8 C9 163.32(13) . . . . ?
B1 N1 C13 C14 89.79(15) . . . . ?
B2 N1 C13 C14 -93.61(15) . . . . ?
N1 C13 C14 C19 -166.87(13) . . . . ?
N1 C13 C14 C15 15.1(2) . . . . ?
C19 C14 C15 C16 0.8(2) . . . . ?
C13 C14 C15 C16 178.87(14) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C15 C16 C17 F1 178.95(15) . . . . ?
C16 C17 C18 C19 0.8(3) . . . . ?
F1 C17 C18 C19 -179.36(16) . . . . ?
C15 C14 C19 C18 -1.2(2) . . . . ?
C13 C14 C19 C18 -179.38(15) . . . . ?
C17 C18 C19 C14 0.5(3) . . . . ?
C1A O2 B1 O1 24.5(3) . . . . ?
C1B O2 B1 O1 -16.2(2) . . . . ?
C1A O2 B1 N1 -157.4(3) . . . . ?
C1B O2 B1 N1 161.85(19) . . . . ?
C2 O1 B1 O2 -3.31(19) . . . . ?
C2 O1 B1 N1 178.71(16) . . . . ?
B2 N1 B1 O2 -171.62(14) . . . . ?
C13 N1 B1 O2 4.6(2) . . . . ?
B2 N1 B1 O1 6.2(2) . . . . ?
C13 N1 B1 O1 -177.61(14) . . . . ?
C7 O3 B2 O4 10.48(15) . . . . ?
C7 O3 B2 N1 -169.61(13) . . . . ?
C8 O4 B2 O3 11.28(15) . . . . ?
C8 O4 B2 N1 -168.65(12) . . . . ?
B1 N1 B2 O3 -9.0(2) . . . . ?
C13 N1 B2 O3 174.82(12) . . . . ?
B1 N1 B2 O4 170.92(13) . . . . ?
C13 N1 B2 O4 -5.27(19) . . . . ?
B1 O2 C1A C6 -154.9(3) . . . . ?
B1 O2 C1A C5A 82.7(4) . . . . ?
B1 O2 C1A C2 -30.8(3) . . . . ?
C3A C2 C1A C6 -73.9(6) . . . . ?
O1 C2 C1A C6 150.1(3) . . . . ?
C4A C2 C1A C6 45.9(4) . . . . ?
C3A C2 C1A O2 163.9(5) . . . . ?
O1 C2 C1A O2 27.9(3) . . . . ?
C4A C2 C1A O2 -76.3(3) . . . . ?
C3A C2 C1A C5A 42.9(6) . . . . ?
O1 C2 C1A C5A -93.2(3) . . . . ?
C4A C2 C1A C5A 162.7(4) . . . . ?
O1 C2 C1B C6 -145.3(2) . . . . ?
C4B C2 C1B C6 94.0(4) . . . . ?
C3B C2 C1B C6 -33.1(4) . . . . ?
O1 C2 C1B C5B 87.3(2) . . . . ?
C4B C2 C1B C5B -33.4(3) . . . . ?
C3B C2 C1B C5B -160.6(2) . . . . ?
O1 C2 C1B O2 -31.0(3) . . . . ?
C4B C2 C1B O2 -151.7(2) . . . . ?
C3B C2 C1B O2 81.2(3) . . . . ?
B1 O2 C1B C2 29.1(3) . . . . ?
B1 O2 C1B C6 156.57(19) . . . . ?
B1 O2 C1B C5B -90.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10A F1 0.97 2.57 3.401(2) 144.0 2_766 yes
C12 H12C O4 0.97 2.60 3.5502(19) 166.1 1_455 yes

_refine_diff_density_max         0.281
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_S0769
_database_code_depnum_ccdc_archive 'CCDC 2129544'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C19 H18 N2 O S'
_chemical_formula_moiety         'C19 H18 N2 O S'
_chemical_formula_weight         322.41
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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'

#------------------------------------------------
_cell_length_a                   8.4071(19)
_cell_length_b                   17.688(4)
_cell_length_c                   11.345(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.767(7)
_cell_angle_gamma                90
_cell_volume                     1638.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    5047
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.24

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.074
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_max          0.258

_exptl_crystal_density_diffrn    1.307
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7040
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            12506
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.178
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999


#==========================================================================
# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_reflns_number_total             3740
_reflns_number_gt                2679
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         3740
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0697
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+0.6139P] where P=(Fo²+2Fc²)/3'

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.047

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
S1 S 0.83093(6) 0.71555(3) 0.77836(4) 0.02956(13) Uani 1 1 d . . . . .
O1 O 0.37538(15) 0.52993(7) 0.24145(12) 0.0371(3) Uani 1 1 d . . . . .
H1A H 0.325000 0.502321 0.185823 0.056 Uiso 1 1 calc R U . . .
N1 N 0.80596(18) 0.55409(8) 0.95212(13) 0.0295(4) Uani 1 1 d . . . . .
N2 N 0.65810(18) 0.64219(8) 0.54258(13) 0.0300(4) Uani 1 1 d . . . . .
H2A H 0.642394 0.634150 0.614618 0.036 Uiso 1 1 calc R U . . .
C1 C 0.7881(2) 0.53238(11) 1.06089(18) 0.0377(5) Uani 1 1 d . . . . .
H1 H 0.705380 0.497214 1.063943 0.045 Uiso 1 1 calc R U . . .
C2 C 0.8836(3) 0.55844(12) 1.16842(18) 0.0420(5) Uani 1 1 d . . . . .
H2 H 0.866427 0.541670 1.243029 0.050 Uiso 1 1 calc R U . . .
C3 C 1.0040(3) 0.60920(13) 1.16450(18) 0.0460(6) Uani 1 1 d . . . . .
H3 H 1.072507 0.627701 1.236597 0.055 Uiso 1 1 calc R U . . .
C4 C 1.0240(2) 0.63310(11) 1.05304(18) 0.0393(5) Uani 1 1 d . . . . .
H4 H 1.105535 0.668557 1.048442 0.047 Uiso 1 1 calc R U . . .
C5 C 0.9231(2) 0.60445(10) 0.94845(15) 0.0270(4) Uani 1 1 d . . . . .
C6 C 0.9406(3) 0.62720(12) 0.82495(17) 0.0406(5) Uani 1 1 d . . . . .
H6A H 0.896401 0.587319 0.766315 0.049 Uiso 1 1 calc R U . . .
H6AB H 1.056751 0.633753 0.826362 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8749(2) 0.72746(9) 0.63414(15) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.9989(2) 0.77576(11) 0.62121(17) 0.0360(5) Uani 1 1 d . . . . .
H8 H 1.056959 0.803016 0.689026 0.043 Uiso 1 1 calc R U . . .
C9 C 1.0395(2) 0.78493(12) 0.51159(18) 0.0393(5) Uani 1 1 d . . . . .
H9 H 1.124011 0.818087 0.504332 0.047 Uiso 1 1 calc R U . . .
C10 C 0.9542(2) 0.74469(10) 0.41247(17) 0.0312(4) Uani 1 1 d . . . . .
H10 H 0.981796 0.750124 0.337350 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8293(2) 0.69677(10) 0.42214(15) 0.0256(4) Uani 1 1 d . . . . .
H11 H 0.773327 0.669509 0.353667 0.031 Uiso 1 1 calc R U . . .
C12 C 0.78422(19) 0.68793(9) 0.53238(14) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.5487(2) 0.60621(10) 0.44021(15) 0.0262(4) Uani 1 1 d . . . . .
H13A H 0.527202 0.641482 0.371617 0.031 Uiso 1 1 calc R U . . .
H13B H 0.444212 0.596187 0.461274 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6121(2) 0.53315(9) 0.40041(15) 0.0233(4) Uani 1 1 d . . . . .
C15 C 0.7566(2) 0.49953(11) 0.46183(16) 0.0297(4) Uani 1 1 d . . . . .
H15 H 0.822630 0.524250 0.529335 0.036 Uiso 1 1 calc R U . . .
C16 C 0.8065(2) 0.43007(11) 0.42613(18) 0.0358(5) Uani 1 1 d . . . . .
H16 H 0.905071 0.408116 0.469132 0.043 Uiso 1 1 calc R U . . .
C17 C 0.7099(2) 0.39355(11) 0.32693(19) 0.0365(5) Uani 1 1 d . . . . .
H17 H 0.742110 0.346233 0.302859 0.044 Uiso 1 1 calc R U . . .
C18 C 0.5663(2) 0.42643(10) 0.26310(17) 0.0314(4) Uani 1 1 d . . . . .
H18 H 0.501688 0.401781 0.194897 0.038 Uiso 1 1 calc R U . . .
C19 C 0.5170(2) 0.49556(10) 0.29918(15) 0.0259(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles, correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
S1 C7 1.7738(18) . ?
S1 C6 1.827(2) . ?
O1 C19 1.359(2) . ?
O1 H1A 0.8300 . ?
N1 C1 1.334(2) . ?
N1 C5 1.336(2) . ?
N2 C12 1.360(2) . ?
N2 C13 1.446(2) . ?
N2 H2A 0.8700 . ?
C1 C2 1.371(3) . ?
C1 H1 0.9400 . ?
C2 C3 1.362(3) . ?
C2 H2 0.9400 . ?
C3 C4 1.381(3) . ?
C3 H3 0.9400 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9400 . ?
C5 C6 1.498(2) . ?
C6 H6A 0.9800 . ?
C6 H6AB 0.9800 . ?
C7 C8 1.382(2) . ?
C7 C12 1.409(2) . ?
C8 C9 1.375(3) . ?
C8 H8 0.9400 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9400 . ?
C10 C11 1.374(2) . ?
C10 H10 0.9400 . ?
C11 C12 1.399(2) . ?
C11 H11 0.9400 . ?
C13 C14 1.508(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 C15 1.382(2) . ?
C14 C19 1.401(2) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9400 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9400 . ?
C17 C18 1.380(3) . ?
C17 H17 0.9400 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9400 . ?

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
C7 S1 C6 99.60(8) . . ?
C19 O1 H1A 109.5 . . ?
C1 N1 C5 117.82(16) . . ?
C12 N2 C13 123.57(14) . . ?
C12 N2 H2A 118.2 . . ?
C13 N2 H2A 118.2 . . ?
N1 C1 C2 123.73(19) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.37(19) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.01(19) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 119.42(19) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
N1 C5 C4 121.65(17) . . ?
N1 C5 C6 116.45(17) . . ?
C4 C5 C6 121.90(18) . . ?
C5 C6 S1 110.19(13) . . ?
C5 C6 H6A 109.6 . . ?
S1 C6 H6A 109.6 . . ?
C5 C6 H6AB 109.6 . . ?
S1 C6 H6AB 109.6 . . ?
H6A C6 H6AB 108.1 . . ?
C8 C7 C12 119.65(16) . . ?
C8 C7 S1 119.96(13) . . ?
C12 C7 S1 120.39(13) . . ?
C9 C8 C7 121.62(17) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C8 C9 C10 118.94(17) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.82(17) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C10 C11 C12 121.00(16) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N2 C12 C11 121.67(15) . . ?
N2 C12 C7 120.42(15) . . ?
C11 C12 C7 117.91(15) . . ?
N2 C13 C14 114.53(14) . . ?
N2 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
N2 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C19 118.07(16) . . ?
C15 C14 C13 123.28(15) . . ?
C19 C14 C13 118.60(15) . . ?
C14 C15 C16 121.56(17) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C17 C16 C15 119.44(17) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C18 C17 C16 120.11(18) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.21(17) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
O1 C19 C18 122.86(16) . . ?
O1 C19 C14 116.52(15) . . ?
C18 C19 C14 120.61(16) . . ?

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
C5 N1 C1 C2 -0.4(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C1 N1 C5 C4 0.5(3) . . . . ?
C1 N1 C5 C6 179.59(16) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 -178.95(18) . . . . ?
N1 C5 C6 S1 96.90(18) . . . . ?
C4 C5 C6 S1 -84.0(2) . . . . ?
C7 S1 C6 C5 179.54(15) . . . . ?
C6 S1 C7 C8 -99.07(17) . . . . ?
C6 S1 C7 C12 80.90(16) . . . . ?
C12 C7 C8 C9 -1.7(3) . . . . ?
S1 C7 C8 C9 178.24(16) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
C13 N2 C12 C11 -7.5(3) . . . . ?
C13 N2 C12 C7 173.20(15) . . . . ?
C10 C11 C12 N2 178.27(17) . . . . ?
C10 C11 C12 C7 -2.4(2) . . . . ?
C8 C7 C12 N2 -177.72(17) . . . . ?
S1 C7 C12 N2 2.3(2) . . . . ?
C8 C7 C12 C11 2.9(2) . . . . ?
S1 C7 C12 C11 -177.04(13) . . . . ?
C12 N2 C13 C14 83.7(2) . . . . ?
N2 C13 C14 C15 5.0(2) . . . . ?
N2 C13 C14 C19 -177.81(15) . . . . ?
C19 C14 C15 C16 -0.8(3) . . . . ?
C13 C14 C15 C16 176.41(16) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C15 C16 C17 C18 0.8(3) . . . . ?
C16 C17 C18 C19 -1.0(3) . . . . ?
C17 C18 C19 O1 -178.65(17) . . . . ?
C17 C18 C19 C14 0.2(3) . . . . ?
C15 C14 C19 O1 179.58(15) . . . . ?
C13 C14 C19 O1 2.3(2) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
C13 C14 C19 C18 -176.67(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1A N1 0.83 1.96 2.7860(19) 174.4 3_666 yes
N2 H2A S1 0.87 2.58 3.0166(15) 112.4 . yes


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_K0572
_database_code_depnum_ccdc_archive 'CCDC 2129545'
loop_
_audit_author_name
_audit_author_address
'Jeffrey Ovens'
;University of Ottawa
Canada
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-06-27 downloaded from the CCDC.
;
#===============================================================================
# 5. CHEMICAL DATA

_chemical_name_systematic        
; 
;

_chemical_formula_sum            'C54 H64 N4 O6 S2 Zn2'
_chemical_formula_moiety         'C38 H32 N4 O2 S2 Zn2, 4(C4 H8 O)'
_chemical_formula_weight         1059.95
#=============================================================
# 6. CRYSTAL DATA

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

#------------------------------------------------
_cell_length_a                   9.9532(13)
_cell_length_b                   10.9777(14)
_cell_length_c                   12.1123(16)
_cell_angle_alpha                88.174(2)
_cell_angle_beta                 83.185(2)
_cell_angle_gamma                80.990(2)
_cell_volume                     1297.7(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    9885
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_min          0.19
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_max          0.241

_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             556
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS

#=============================================================================
# 7. EXPERIMENTAL DATA

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      203(2)
_diffrn_reflns_number            31432
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.693
_diffrn_reflns_theta_max         30.665
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000


#==========================================================================
# 8. REFINEMENT DATA

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_reflns_number_total             8030
_reflns_number_gt                5376
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_special_details          none

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details none
_refine_ls_abs_structure_Flack   .
_refine_ls_number_reflns         8030
_refine_ls_number_parameters     399
_refine_ls_number_restraints     612
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1520
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0852P)²+0.2735P] where P=(Fo²+2Fc²)/3'

#---------------------------------------------------------


#========================================================== 
# 9. General computing 

_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_cell_refinement       'Bruker SAINT'
_computing_structure_solution    
; 
 SHELXT 2014/5 (Sheldrick, 2014)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_shelx_SHELXL_version_number     2018/3

#===================================================================
# 10.  ATOMIC COORDINATES AND THERMAL PARAMETERS

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom

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'
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'
S S 0.1246 0.1234 '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'

#==============================================================================
# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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 0.09246(3) 0.52844(3) 0.58868(2) 0.03788(11) Uani 1 1 d . . . . .
C1 C 0.0992(2) 0.6713(2) 0.3797(2) 0.0406(5) Uani 1 1 d . . . . .
S1 S 0.16053(8) 0.48020(7) 0.78609(6) 0.04964(18) Uani 1 1 d . . . . .
N1 N 0.0799(2) 0.6974(2) 0.63602(17) 0.0442(5) Uani 1 1 d . . . . .
O1 O 0.04550(18) 0.57661(17) 0.43054(14) 0.0431(4) Uani 1 1 d . . . . .
C2 C 0.1533(3) 0.6631(3) 0.2673(2) 0.0505(6) Uani 1 1 d . . . . .
H2 H 0.148861 0.592287 0.227014 0.061 Uiso 1 1 calc R U . . .
N2 N 0.2846(2) 0.4306(2) 0.54689(19) 0.0440(5) Uani 1 1 d . . . . .
C6 C 0.1036(3) 0.7769(2) 0.4388(2) 0.0426(6) Uani 1 1 d . . . . .
C5 C 0.1664(3) 0.8707(3) 0.3840(3) 0.0560(7) Uani 1 1 d . . . . .
H5 H 0.171662 0.942217 0.422919 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2213(3) 0.8604(3) 0.2726(3) 0.0637(8) Uani 1 1 d . . . . .
H4 H 0.264035 0.924105 0.237270 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2128(3) 0.7583(3) 0.2158(3) 0.0622(8) Uani 1 1 d . . . . .
H3 H 0.247852 0.752305 0.140265 0.075 Uiso 1 1 calc R U . . .
C9 C -0.0052(4) 0.8405(3) 0.7890(3) 0.0641(8) Uani 1 1 d . . . . .
H9 H -0.034647 0.904141 0.739583 0.077 Uiso 1 1 calc R U . . .
C8 C 0.0559(3) 0.7246(3) 0.7460(2) 0.0485(6) Uani 1 1 d . . . . .
C7 C 0.0366(3) 0.7961(2) 0.5573(2) 0.0497(6) Uani 1 1 d . . . . .
H7A H 0.056715 0.874023 0.583669 0.060 Uiso 1 1 calc R U . . .
H7AB H -0.062851 0.804115 0.557251 0.060 Uiso 1 1 calc R U . . .
C10 C -0.0233(5) 0.8636(4) 0.9024(3) 0.0791(11) Uani 1 1 d . . . . .
H10 H -0.063450 0.942555 0.927559 0.095 Uiso 1 1 calc R U . . .
C11 C 0.0162(4) 0.7730(4) 0.9791(3) 0.0765(11) Uani 1 1 d . . . . .
H11 H 0.004549 0.789799 1.055552 0.092 Uiso 1 1 calc R U . . .
C12 C 0.0729(3) 0.6584(4) 0.9407(2) 0.0631(8) Uani 1 1 d . . . . .
H12 H 0.098811 0.595581 0.992023 0.076 Uiso 1 1 calc R U . . .
C13 C 0.0932(3) 0.6322(3) 0.8277(2) 0.0488(6) Uani 1 1 d . . . . .
C14 C 0.3354(3) 0.4959(3) 0.7240(3) 0.0598(8) Uani 1 1 d . . . . .
H14A H 0.340188 0.583244 0.707710 0.072 Uiso 1 1 calc R U . . .
H14B H 0.399779 0.467396 0.778037 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3775(3) 0.4240(3) 0.6195(2) 0.0493(6) Uani 1 1 d . . . . .
C16 C 0.5079(3) 0.3583(3) 0.5948(3) 0.0649(9) Uani 1 1 d . . . . .
H16 H 0.572382 0.354381 0.646030 0.078 Uiso 1 1 calc R U . . .
C17 C 0.5420(3) 0.2990(3) 0.4950(3) 0.0709(9) Uani 1 1 d . . . . .
H17 H 0.630328 0.254860 0.477183 0.085 Uiso 1 1 calc R U . . .
C18 C 0.4463(3) 0.3046(3) 0.4213(3) 0.0663(9) Uani 1 1 d . . . . .
H18 H 0.467173 0.262938 0.353369 0.080 Uiso 1 1 calc R U . . .
C19 C 0.3188(3) 0.3729(3) 0.4496(3) 0.0524(7) Uani 1 1 d . . . . .
H19 H 0.253712 0.379130 0.398678 0.063 Uiso 1 1 calc R U . . .
O1_1 O 0.4285(7) 0.3758(7) 0.1380(6) 0.181(3) Uani 0.704(6) 1 d D U P A 1
C1_1 C 0.3074(7) 0.3249(9) 0.1101(8) 0.170(3) Uani 0.704(6) 1 d D U P A 1
H1A_1 H 0.248144 0.309351 0.177971 0.204 Uiso 0.704(6) 1 calc R U P A 1
H1AB_1 H 0.254313 0.383116 0.062664 0.204 Uiso 0.704(6) 1 calc R U P A 1
C2_1 C 0.3566(8) 0.2157(8) 0.0545(8) 0.172(4) Uani 0.704(6) 1 d D U P A 1
H2A_1 H 0.355696 0.145560 0.106601 0.207 Uiso 0.704(6) 1 calc R U P A 1
H2B_1 H 0.298553 0.204801 -0.003306 0.207 Uiso 0.704(6) 1 calc R U P A 1
C3_1 C 0.4853(7) 0.2210(8) 0.0083(7) 0.157(3) Uani 0.704(6) 1 d D U P A 1
H3A_1 H 0.485469 0.242418 -0.070832 0.188 Uiso 0.704(6) 1 calc R U P A 1
H3B_1 H 0.542256 0.140396 0.015053 0.188 Uiso 0.704(6) 1 calc R U P A 1
C4_1 C 0.5387(7) 0.3105(9) 0.0629(8) 0.163(3) Uani 0.704(6) 1 d D U P A 1
H4A_1 H 0.575867 0.368157 0.008466 0.196 Uiso 0.704(6) 1 calc R U P A 1
H4AB_1 H 0.612708 0.270986 0.104618 0.196 Uiso 0.704(6) 1 calc R U P A 1
O1_2 O 0.4606(16) 0.2313(16) 0.1590(10) 0.200(6) Uani 0.296(6) 1 d D U P A 2
C1_2 C 0.3319(13) 0.3145(18) 0.1424(12) 0.173(5) Uani 0.296(6) 1 d D U P A 2
H1A_2 H 0.259412 0.266449 0.131817 0.207 Uiso 0.296(6) 1 calc R U P A 2
H1AB_2 H 0.301459 0.367208 0.207257 0.207 Uiso 0.296(6) 1 calc R U P A 2
C2_2 C 0.3604(17) 0.3856(15) 0.0485(13) 0.175(7) Uani 0.296(6) 1 d D U P A 2
H2A_2 H 0.280866 0.400868 0.006603 0.210 Uiso 0.296(6) 1 calc R U P A 2
H2B_2 H 0.381201 0.465324 0.070032 0.210 Uiso 0.296(6) 1 calc R U P A 2
C3_2 C 0.4686(18) 0.3245(17) -0.0147(10) 0.186(7) Uani 0.296(6) 1 d D U P A 2
H3A_2 H 0.531073 0.381744 -0.043442 0.223 Uiso 0.296(6) 1 calc R U P A 2
H3B_2 H 0.437568 0.288034 -0.078175 0.223 Uiso 0.296(6) 1 calc R U P A 2
C4_2 C 0.5371(15) 0.2312(16) 0.0493(12) 0.168(4) Uani 0.296(6) 1 d D U P A 2
H4A_2 H 0.630373 0.246781 0.054858 0.202 Uiso 0.296(6) 1 calc R U P A 2
H4AB_2 H 0.542782 0.150942 0.014410 0.202 Uiso 0.296(6) 1 calc R U P A 2
O1_3 O -0.2148(8) 0.8896(10) 0.3107(9) 0.173(3) Uani 0.497(6) 1 d D U P B 1
C1_3 C -0.3134(10) 0.9959(11) 0.3578(9) 0.154(4) Uani 0.497(6) 1 d D U P B 1
H1A_3 H -0.322700 0.991762 0.439262 0.185 Uiso 0.497(6) 1 calc R U P B 1
H1AB_3 H -0.281902 1.073655 0.333434 0.185 Uiso 0.497(6) 1 calc R U P B 1
C2_3 C -0.4375(8) 0.9886(11) 0.3194(9) 0.131(3) Uani 0.497(6) 1 d D U P B 1
H2A_3 H -0.496855 0.950994 0.376573 0.157 Uiso 0.497(6) 1 calc R U P B 1
H2B_3 H -0.483635 1.071463 0.302380 0.157 Uiso 0.497(6) 1 calc R U P B 1
C3_3 C -0.4142(9) 0.9199(11) 0.2273(8) 0.137(4) Uani 0.497(6) 1 d D U P B 1
H3A_3 H -0.431181 0.972678 0.162066 0.164 Uiso 0.497(6) 1 calc R U P B 1
H3B_3 H -0.476687 0.858685 0.232721 0.164 Uiso 0.497(6) 1 calc R U P B 1
C4_3 C -0.2782(11) 0.8598(12) 0.2151(9) 0.168(5) Uani 0.497(6) 1 d D U P B 1
H4A_3 H -0.228833 0.887674 0.146391 0.201 Uiso 0.497(6) 1 calc R U P B 1
H4AB_3 H -0.275705 0.770418 0.211299 0.201 Uiso 0.497(6) 1 calc R U P B 1
O1_4 O -0.2685(10) 0.9045(11) 0.3705(7) 0.187(4) Uani 0.503(6) 1 d D U P B 2
C1_4 C -0.4082(10) 0.9704(11) 0.3588(8) 0.161(4) Uani 0.503(6) 1 d D U P B 2
H1A_4 H -0.470200 0.911447 0.349187 0.193 Uiso 0.503(6) 1 calc R U P B 2
H1AB_4 H -0.444327 1.019375 0.424998 0.193 Uiso 0.503(6) 1 calc R U P B 2
C2_4 C -0.3962(9) 1.0464(9) 0.2657(8) 0.123(3) Uani 0.503(6) 1 d D U P B 2
H2A_4 H -0.476919 1.049982 0.225838 0.148 Uiso 0.503(6) 1 calc R U P B 2
H2B_4 H -0.390084 1.130176 0.288078 0.148 Uiso 0.503(6) 1 calc R U P B 2
C3_4 C -0.2828(11) 1.0007(12) 0.1993(7) 0.165(5) Uani 0.503(6) 1 d D U P B 2
H3A_4 H -0.231129 1.067360 0.173966 0.198 Uiso 0.503(6) 1 calc R U P B 2
H3B_4 H -0.308221 0.963573 0.133816 0.198 Uiso 0.503(6) 1 calc R U P B 2
C4_4 C -0.2010(11) 0.9113(12) 0.2579(9) 0.169(4) Uani 0.503(6) 1 d D U P B 2
H4A_4 H -0.109945 0.934240 0.258931 0.203 Uiso 0.503(6) 1 calc R U P B 2
H4AB_4 H -0.190534 0.830994 0.222067 0.203 Uiso 0.503(6) 1 calc R U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 N1 1.940(2) . ?
Zn1 O1 1.9643(17) 2_566 ?
Zn1 N2 2.056(2) . ?
Zn1 O1 2.0585(17) . ?
Zn1 S1 2.5784(8) . ?
Zn1 Zn1 3.1267(6) 2_566 ?
C1 O1 1.341(3) . ?
C1 C6 1.392(4) . ?
C1 C2 1.404(4) . ?
S1 C13 1.763(3) . ?
S1 C14 1.843(3) . ?
N1 C8 1.360(3) . ?
N1 C7 1.468(3) . ?
C2 C3 1.378(5) . ?
C2 H2 0.9400 . ?
N2 C19 1.338(4) . ?
N2 C15 1.342(3) . ?
C6 C5 1.396(4) . ?
C6 C7 1.515(4) . ?
C5 C4 1.396(5) . ?
C5 H5 0.9400 . ?
C4 C3 1.353(5) . ?
C4 H4 0.9400 . ?
C3 H3 0.9400 . ?
C9 C10 1.390(4) . ?
C9 C8 1.409(4) . ?
C9 H9 0.9400 . ?
C8 C13 1.432(4) . ?
C7 H7A 0.9800 . ?
C7 H7AB 0.9800 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9400 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.393(4) . ?
C12 H12 0.9400 . ?
C14 C15 1.496(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 C16 1.386(4) . ?
C16 C17 1.372(5) . ?
C16 H16 0.9400 . ?
C17 C18 1.373(5) . ?
C17 H17 0.9400 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9400 . ?
C19 H19 0.9400 . ?
O1_1 C4_1 1.451(6) . ?
O1_1 C1_1 1.483(6) . ?
C1_1 C2_1 1.386(6) . ?
C1_1 H1A_1 0.9800 . ?
C1_1 H1AB_1 0.9800 . ?
C2_1 C3_1 1.345(6) . ?
C2_1 H2A_1 0.9800 . ?
C2_1 H2B_1 0.9800 . ?
C3_1 C4_1 1.404(6) . ?
C3_1 H3A_1 0.9800 . ?
C3_1 H3B_1 0.9800 . ?
C4_1 H4A_1 0.9800 . ?
C4_1 H4AB_1 0.9800 . ?
O1_2 C4_2 1.451(6) . ?
O1_2 C1_2 1.483(6) . ?
C1_2 C2_2 1.386(6) . ?
C1_2 H1A_2 0.9800 . ?
C1_2 H1AB_2 0.9800 . ?
C2_2 C3_2 1.344(6) . ?
C2_2 H2A_2 0.9800 . ?
C2_2 H2B_2 0.9800 . ?
C3_2 C4_2 1.404(6) . ?
C3_2 H3A_2 0.9800 . ?
C3_2 H3B_2 0.9800 . ?
C4_2 H4A_2 0.9800 . ?
C4_2 H4AB_2 0.9800 . ?
O1_3 C4_3 1.452(6) . ?
O1_3 C1_3 1.484(7) . ?
C1_3 C2_3 1.385(6) . ?
C1_3 H1A_3 0.9800 . ?
C1_3 H1AB_3 0.9800 . ?
C2_3 C3_3 1.343(6) . ?
C2_3 H2A_3 0.9800 . ?
C2_3 H2B_3 0.9800 . ?
C3_3 C4_3 1.403(6) . ?
C3_3 H3A_3 0.9800 . ?
C3_3 H3B_3 0.9800 . ?
C4_3 H4A_3 0.9800 . ?
C4_3 H4AB_3 0.9800 . ?
O1_4 C4_4 1.452(6) . ?
O1_4 C1_4 1.484(7) . ?
C1_4 C2_4 1.386(6) . ?
C1_4 H1A_4 0.9800 . ?
C1_4 H1AB_4 0.9800 . ?
C2_4 C3_4 1.344(6) . ?
C2_4 H2A_4 0.9800 . ?
C2_4 H2B_4 0.9800 . ?
C3_4 C4_4 1.404(6) . ?
C3_4 H3A_4 0.9800 . ?
C3_4 H3B_4 0.9800 . ?
C4_4 H4A_4 0.9800 . ?
C4_4 H4AB_4 0.9800 . ?

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
N1 Zn1 O1 133.08(9) . 2_566 ?
N1 Zn1 N2 117.72(9) . . ?
O1 Zn1 N2 109.20(9) 2_566 . ?
N1 Zn1 O1 94.49(8) . . ?
O1 Zn1 O1 78.01(8) 2_566 . ?
N2 Zn1 O1 98.21(8) . . ?
N1 Zn1 S1 82.48(6) . . ?
O1 Zn1 S1 105.78(5) 2_566 . ?
N2 Zn1 S1 81.21(6) . . ?
O1 Zn1 S1 176.16(5) . . ?
N1 Zn1 Zn1 118.73(6) . 2_566 ?
O1 Zn1 Zn1 40.09(5) 2_566 2_566 ?
N2 Zn1 Zn1 107.50(6) . 2_566 ?
O1 Zn1 Zn1 37.92(5) . 2_566 ?
S1 Zn1 Zn1 145.87(2) . 2_566 ?
O1 C1 C6 120.1(2) . . ?
O1 C1 C2 120.0(2) . . ?
C6 C1 C2 119.8(3) . . ?
C13 S1 C14 102.32(15) . . ?
C13 S1 Zn1 90.85(9) . . ?
C14 S1 Zn1 85.46(9) . . ?
C8 N1 C7 117.1(2) . . ?
C8 N1 Zn1 120.06(18) . . ?
C7 N1 Zn1 117.58(16) . . ?
C1 O1 Zn1 139.66(14) . 2_566 ?
C1 O1 Zn1 117.75(14) . . ?
Zn1 O1 Zn1 101.99(8) 2_566 . ?
C3 C2 C1 120.3(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C19 N2 C15 119.3(2) . . ?
C19 N2 Zn1 121.64(18) . . ?
C15 N2 Zn1 119.04(19) . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 122.4(2) . . ?
C5 C6 C7 119.4(3) . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C3 C2 120.8(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C10 C9 C8 122.0(3) . . ?
C10 C9 H9 119.0 . . ?
C8 C9 H9 119.0 . . ?
N1 C8 C9 124.7(3) . . ?
N1 C8 C13 120.2(3) . . ?
C9 C8 C13 115.1(3) . . ?
N1 C7 C6 114.9(2) . . ?
N1 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
N1 C7 H7AB 108.6 . . ?
C6 C7 H7AB 108.6 . . ?
H7A C7 H7AB 107.5 . . ?
C11 C10 C9 121.5(4) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 118.2(3) . . ?
C12 C11 H11 120.9 . . ?
C10 C11 H11 120.9 . . ?
C11 C12 C13 121.8(3) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 121.3(3) . . ?
C12 C13 S1 118.7(2) . . ?
C8 C13 S1 119.9(2) . . ?
C15 C14 S1 112.5(2) . . ?
C15 C14 H14A 109.1 . . ?
S1 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
S1 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
N2 C15 C16 120.8(3) . . ?
N2 C15 C14 116.7(2) . . ?
C16 C15 C14 122.4(3) . . ?
C17 C16 C15 119.5(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 119.7(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 118.3(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
N2 C19 C18 122.4(3) . . ?
N2 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C4_1 O1_1 C1_1 102.5(5) . . ?
C2_1 C1_1 O1_1 106.8(5) . . ?
C2_1 C1_1 H1A_1 110.4 . . ?
O1_1 C1_1 H1A_1 110.4 . . ?
C2_1 C1_1 H1AB_1 110.4 . . ?
O1_1 C1_1 H1AB_1 110.4 . . ?
H1A_1 C1_1 H1AB_1 108.6 . . ?
C3_1 C2_1 C1_1 108.2(5) . . ?
C3_1 C2_1 H2A_1 110.1 . . ?
C1_1 C2_1 H2A_1 110.1 . . ?
C3_1 C2_1 H2B_1 110.1 . . ?
C1_1 C2_1 H2B_1 110.1 . . ?
H2A_1 C2_1 H2B_1 108.4 . . ?
C2_1 C3_1 C4_1 109.2(5) . . ?
C2_1 C3_1 H3A_1 109.8 . . ?
C4_1 C3_1 H3A_1 109.8 . . ?
C2_1 C3_1 H3B_1 109.8 . . ?
C4_1 C3_1 H3B_1 109.8 . . ?
H3A_1 C3_1 H3B_1 108.3 . . ?
C3_1 C4_1 O1_1 107.9(5) . . ?
C3_1 C4_1 H4A_1 110.1 . . ?
O1_1 C4_1 H4A_1 110.1 . . ?
C3_1 C4_1 H4AB_1 110.1 . . ?
O1_1 C4_1 H4AB_1 110.1 . . ?
H4A_1 C4_1 H4AB_1 108.4 . . ?
C4_2 O1_2 C1_2 102.2(5) . . ?
C2_2 C1_2 O1_2 106.7(5) . . ?
C2_2 C1_2 H1A_2 110.4 . . ?
O1_2 C1_2 H1A_2 110.4 . . ?
C2_2 C1_2 H1AB_2 110.4 . . ?
O1_2 C1_2 H1AB_2 110.4 . . ?
H1A_2 C1_2 H1AB_2 108.6 . . ?
C3_2 C2_2 C1_2 108.4(5) . . ?
C3_2 C2_2 H2A_2 110.0 . . ?
C1_2 C2_2 H2A_2 110.0 . . ?
C3_2 C2_2 H2B_2 110.0 . . ?
C1_2 C2_2 H2B_2 110.0 . . ?
H2A_2 C2_2 H2B_2 108.4 . . ?
C2_2 C3_2 C4_2 109.5(5) . . ?
C2_2 C3_2 H3A_2 109.8 . . ?
C4_2 C3_2 H3A_2 109.8 . . ?
C2_2 C3_2 H3B_2 109.8 . . ?
C4_2 C3_2 H3B_2 109.8 . . ?
H3A_2 C3_2 H3B_2 108.2 . . ?
C3_2 C4_2 O1_2 107.9(5) . . ?
C3_2 C4_2 H4A_2 110.1 . . ?
O1_2 C4_2 H4A_2 110.1 . . ?
C3_2 C4_2 H4AB_2 110.1 . . ?
O1_2 C4_2 H4AB_2 110.1 . . ?
H4A_2 C4_2 H4AB_2 108.4 . . ?
C4_3 O1_3 C1_3 101.9(5) . . ?
C2_3 C1_3 O1_3 106.7(5) . . ?
C2_3 C1_3 H1A_3 110.4 . . ?
O1_3 C1_3 H1A_3 110.4 . . ?
C2_3 C1_3 H1AB_3 110.4 . . ?
O1_3 C1_3 H1AB_3 110.4 . . ?
H1A_3 C1_3 H1AB_3 108.6 . . ?
C3_3 C2_3 C1_3 108.8(5) . . ?
C3_3 C2_3 H2A_3 109.9 . . ?
C1_3 C2_3 H2A_3 109.9 . . ?
C3_3 C2_3 H2B_3 109.9 . . ?
C1_3 C2_3 H2B_3 109.9 . . ?
H2A_3 C2_3 H2B_3 108.3 . . ?
C2_3 C3_3 C4_3 109.7(5) . . ?
C2_3 C3_3 H3A_3 109.7 . . ?
C4_3 C3_3 H3A_3 109.7 . . ?
C2_3 C3_3 H3B_3 109.7 . . ?
C4_3 C3_3 H3B_3 109.7 . . ?
H3A_3 C3_3 H3B_3 108.2 . . ?
C3_3 C4_3 O1_3 107.7(5) . . ?
C3_3 C4_3 H4A_3 110.2 . . ?
O1_3 C4_3 H4A_3 110.2 . . ?
C3_3 C4_3 H4AB_3 110.2 . . ?
O1_3 C4_3 H4AB_3 110.2 . . ?
H4A_3 C4_3 H4AB_3 108.5 . . ?
C4_4 O1_4 C1_4 101.9(5) . . ?
C2_4 C1_4 O1_4 106.5(5) . . ?
C2_4 C1_4 H1A_4 110.4 . . ?
O1_4 C1_4 H1A_4 110.4 . . ?
C2_4 C1_4 H1AB_4 110.4 . . ?
O1_4 C1_4 H1AB_4 110.4 . . ?
H1A_4 C1_4 H1AB_4 108.6 . . ?
C3_4 C2_4 C1_4 108.6(5) . . ?
C3_4 C2_4 H2A_4 110.0 . . ?
C1_4 C2_4 H2A_4 110.0 . . ?
C3_4 C2_4 H2B_4 110.0 . . ?
C1_4 C2_4 H2B_4 110.0 . . ?
H2A_4 C2_4 H2B_4 108.4 . . ?
C2_4 C3_4 C4_4 109.7(5) . . ?
C2_4 C3_4 H3A_4 109.7 . . ?
C4_4 C3_4 H3A_4 109.7 . . ?
C2_4 C3_4 H3B_4 109.7 . . ?
C4_4 C3_4 H3B_4 109.7 . . ?
H3A_4 C3_4 H3B_4 108.2 . . ?
C3_4 C4_4 O1_4 107.7(5) . . ?
C3_4 C4_4 H4A_4 110.2 . . ?
O1_4 C4_4 H4A_4 110.2 . . ?
C3_4 C4_4 H4AB_4 110.2 . . ?
O1_4 C4_4 H4AB_4 110.2 . . ?
H4A_4 C4_4 H4AB_4 108.5 . . ?

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
C6 C1 O1 Zn1 127.4(2) . . . 2_566 ?
C2 C1 O1 Zn1 -53.7(4) . . . 2_566 ?
C6 C1 O1 Zn1 -41.7(3) . . . . ?
C2 C1 O1 Zn1 137.1(2) . . . . ?
O1 C1 C2 C3 -177.8(2) . . . . ?
C6 C1 C2 C3 1.1(4) . . . . ?
O1 C1 C6 C5 177.0(2) . . . . ?
C2 C1 C6 C5 -1.9(4) . . . . ?
O1 C1 C6 C7 -6.4(4) . . . . ?
C2 C1 C6 C7 174.7(2) . . . . ?
C1 C6 C5 C4 1.0(4) . . . . ?
C7 C6 C5 C4 -175.7(3) . . . . ?
C6 C5 C4 C3 0.7(5) . . . . ?
C5 C4 C3 C2 -1.5(5) . . . . ?
C1 C2 C3 C4 0.6(5) . . . . ?
C7 N1 C8 C9 -1.0(4) . . . . ?
Zn1 N1 C8 C9 -154.7(3) . . . . ?
C7 N1 C8 C13 178.9(3) . . . . ?
Zn1 N1 C8 C13 25.1(4) . . . . ?
C10 C9 C8 N1 -178.1(3) . . . . ?
C10 C9 C8 C13 2.1(5) . . . . ?
C8 N1 C7 C6 161.3(2) . . . . ?
Zn1 N1 C7 C6 -44.3(3) . . . . ?
C1 C6 C7 N1 55.2(3) . . . . ?
C5 C6 C7 N1 -128.2(3) . . . . ?
C8 C9 C10 C11 -0.9(6) . . . . ?
C9 C10 C11 C12 -0.8(7) . . . . ?
C10 C11 C12 C13 1.1(6) . . . . ?
C11 C12 C13 C8 0.2(5) . . . . ?
C11 C12 C13 S1 -177.5(3) . . . . ?
N1 C8 C13 C12 178.4(3) . . . . ?
C9 C8 C13 C12 -1.7(4) . . . . ?
N1 C8 C13 S1 -3.9(4) . . . . ?
C9 C8 C13 S1 175.9(2) . . . . ?
C14 S1 C13 C12 -108.4(3) . . . . ?
Zn1 S1 C13 C12 166.1(2) . . . . ?
C14 S1 C13 C8 73.9(3) . . . . ?
Zn1 S1 C13 C8 -11.6(2) . . . . ?
C13 S1 C14 C15 -138.5(2) . . . . ?
Zn1 S1 C14 C15 -48.6(2) . . . . ?
C19 N2 C15 C16 0.0(4) . . . . ?
Zn1 N2 C15 C16 179.6(2) . . . . ?
C19 N2 C15 C14 176.9(3) . . . . ?
Zn1 N2 C15 C14 -3.6(4) . . . . ?
S1 C14 C15 N2 43.9(3) . . . . ?
S1 C14 C15 C16 -139.3(3) . . . . ?
N2 C15 C16 C17 -0.2(5) . . . . ?
C14 C15 C16 C17 -176.9(3) . . . . ?
C15 C16 C17 C18 -0.6(6) . . . . ?
C16 C17 C18 C19 1.5(6) . . . . ?
C15 N2 C19 C18 1.0(5) . . . . ?
Zn1 N2 C19 C18 -178.5(2) . . . . ?
C17 C18 C19 N2 -1.8(5) . . . . ?
C4_1 O1_1 C1_1 C2_1 18.3(10) . . . . ?
O1_1 C1_1 C2_1 C3_1 -24.3(10) . . . . ?
C1_1 C2_1 C3_1 C4_1 20.3(10) . . . . ?
C2_1 C3_1 C4_1 O1_1 -8.0(10) . . . . ?
C1_1 O1_1 C4_1 C3_1 -6.5(10) . . . . ?
C4_2 O1_2 C1_2 C2_2 -20.6(11) . . . . ?
O1_2 C1_2 C2_2 C3_2 23.7(11) . . . . ?
C1_2 C2_2 C3_2 C4_2 -17.0(13) . . . . ?
C2_2 C3_2 C4_2 O1_2 3.1(14) . . . . ?
C1_2 O1_2 C4_2 C3_2 10.7(13) . . . . ?
C4_3 O1_3 C1_3 C2_3 22.0(9) . . . . ?
O1_3 C1_3 C2_3 C3_3 -21.5(11) . . . . ?
C1_3 C2_3 C3_3 C4_3 11.8(13) . . . . ?
C2_3 C3_3 C4_3 O1_3 3.0(13) . . . . ?
C1_3 O1_3 C4_3 C3_3 -15.1(10) . . . . ?
C4_4 O1_4 C1_4 C2_4 -22.9(9) . . . . ?
O1_4 C1_4 C2_4 C3_4 23.2(11) . . . . ?
C1_4 C2_4 C3_4 C4_4 -13.6(13) . . . . ?
C2_4 C3_4 C4_4 O1_4 -1.8(13) . . . . ?
C1_4 O1_4 C4_4 C3_4 15.0(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C18 H18 O1_2^b 0.94 2.40 3.284(15) 156.4 . yes
C4_3^a H4AB_3^a S1 0.98 2.81 3.733(12) 157.0 2_566 yes
C2_4^b H2A_4^b O1_2^b 0.98 2.15 2.680(16) 112.2 1_465 yes

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.072


