# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2024

####################################################################### 
# 
# 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_k10911-chl-a(sq-dioxide)
_database_code_depnum_ccdc_archive 'CCDC 2272046'
loop_
_audit_author_name
_audit_author_address
'Yu-Lun Chang'
;Department of Medicinal and Applied Chemistry, Kaohsiung Medical University 
Taiwan
;
_audit_update_record             
;
2023-06-24 deposited with the CCDC.	2024-08-15 downloaded from the CCDC.
;
_audit_creation_date             2020-11-02
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H24 B F2 N3 O2)'
_chemical_formula_sum            'C34 H50 B2 F4 N6 O4'
_chemical_formula_weight         704.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H2 N3 O2 F2 B'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.00305(16)
_cell_length_b                   17.8739(4)
_cell_length_c                   21.0833(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.3815(15)
_cell_angle_gamma                90
_cell_volume                     3391.73(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15163
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      26.8830
_cell_measurement_theta_min      2.2920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.10962
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            32271
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.279
_diffrn_ambient_temperature      113(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  25.00   0.50   63.34    --   10.60  11.00-160.00   72
  2  ω    -16.00  10.00   0.50   63.34    --  -10.90  11.00-160.00   52
  3  ω     44.00 100.00   0.50   63.34    --   10.60  82.00  30.00  112
  4  ω     21.00  65.00   0.50   63.34    --   10.60  82.00 -30.00   88
  5  ω     35.00  61.00   0.50   63.34    --   10.60  82.00 -90.00   52
  6  ω     -2.00  24.00   0.50   63.34    --   10.60  82.00 -90.00   52
  7  ω    -58.00  36.00   0.50   63.34    --   10.60 -77.00  30.00  188
  8  ω     -4.00  37.00   0.50   63.34    --   10.60  77.00 -60.00   82
  9  ω     40.00  66.00   0.50   63.34    --   10.60  77.00 -60.00   52
 10  ω    -11.00  37.00   0.50   63.34    --   10.60  82.00   0.00   96
 11  ω    -29.00  20.00   0.50   63.34    --  -10.90 -57.00  30.00   98
 12  ω    -60.00 -34.00   0.50   63.34    --  -10.90 -57.00  30.00   52
 13  ω    -41.00  70.00   0.50   63.34    --  -10.90  38.00 150.00  222
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro II AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0780990000
_diffrn_orient_matrix_UB_12      -0.0024038000
_diffrn_orient_matrix_UB_13      0.0051610000
_diffrn_orient_matrix_UB_21      -0.0095522000
_diffrn_orient_matrix_UB_22      0.0054448000
_diffrn_orient_matrix_UB_23      0.0329559000
_diffrn_orient_matrix_UB_31      -0.0061048000
_diffrn_orient_matrix_UB_32      -0.0392110000
_diffrn_orient_matrix_UB_33      0.0042312000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4951
_reflns_number_total             5960
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.56a (Rigaku OD, 2020)'
_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  (Sheldrick, 2015)'
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         5960
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+1.8202P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1160
_refine_ls_wR_factor_ref         0.1212
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  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.a Ternary CH refined with riding coordinates:
 C15(H15), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C31(H31A,H31B), C33(H33A,
 H33B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C10(H10), N6(H6), C21(H21), C27(H27)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.29986(12) 0.83773(6) 0.08237(5) 0.0284(3) Uani 1 1 d . . . . .
F2 F 0.10530(12) 0.76629(6) 0.11297(5) 0.0258(3) Uani 1 1 d . . . . .
O1 O 0.18032(18) 0.79423(10) 0.47638(8) 0.0448(4) Uani 1 1 d . . . . .
H1 H 0.170(4) 0.793(2) 0.4305(18) 0.092(12) Uiso 1 1 d . . . . .
O2 O 0.50429(16) 0.63163(8) 0.44158(7) 0.0267(3) Uani 1 1 d . . . . .
H2 H 0.580(3) 0.6045(15) 0.4475(12) 0.051(8) Uiso 1 1 d . . . . .
N1 N 0.21096(16) 0.85395(8) 0.18830(7) 0.0185(3) Uani 1 1 d . . . . .
N2 N 0.34823(17) 0.73922(9) 0.15830(7) 0.0190(3) Uani 1 1 d . . . . .
N3 N 0.36087(16) 0.75524(9) 0.37667(7) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.277539 0.733511 0.368123 0.023 Uiso 1 1 calc R U . . .
C1 C 0.37662(19) 0.79188(10) 0.26424(8) 0.0174(4) Uani 1 1 d . . . . .
C2 C 0.27647(19) 0.84960(10) 0.24922(8) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.2220(2) 0.91145(10) 0.28495(9) 0.0206(4) Uani 1 1 d . . . . .
C4 C 0.1267(2) 0.95024(11) 0.24449(9) 0.0232(4) Uani 1 1 d . . . . .
H4 H 0.074082 0.993121 0.254874 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1222(2) 0.91468(11) 0.18541(9) 0.0217(4) Uani 1 1 d . . . . .
C6 C 0.2541(2) 0.93386(11) 0.35243(9) 0.0247(4) Uani 1 1 d . . . . .
H6A H 0.239120 0.891715 0.379766 0.037 Uiso 1 1 calc R U . . .
H6B H 0.188599 0.973700 0.363990 0.037 Uiso 1 1 calc R U . . .
H6C H 0.355249 0.950500 0.356724 0.037 Uiso 1 1 calc R U . . .
C7 C 0.0390(2) 0.93741(12) 0.12641(10) 0.0292(5) Uani 1 1 d . . . . .
H7A H 0.108145 0.951694 0.094628 0.044 Uiso 1 1 calc R U . . .
H7B H -0.024538 0.978973 0.135519 0.044 Uiso 1 1 calc R U . . .
H7C H -0.020053 0.896167 0.111132 0.044 Uiso 1 1 calc R U . . .
C8 C 0.41144(19) 0.73643(10) 0.22002(8) 0.0181(4) Uani 1 1 d . . . . .
C9 C 0.5063(2) 0.67217(11) 0.22297(9) 0.0212(4) Uani 1 1 d . . . . .
C10 C 0.4976(2) 0.63930(11) 0.16383(9) 0.0257(4) Uani 1 1 d . . . . .
H10 H 0.547725 0.596259 0.151840 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4012(2) 0.68115(11) 0.12480(9) 0.0238(4) Uani 1 1 d . . . . .
C12 C 0.6002(2) 0.64193(11) 0.27701(9) 0.0267(4) Uani 1 1 d . . . . .
H12A H 0.680969 0.675681 0.286008 0.040 Uiso 1 1 calc R U . . .
H12B H 0.639016 0.593877 0.265616 0.040 Uiso 1 1 calc R U . . .
H12C H 0.540681 0.636933 0.313941 0.040 Uiso 1 1 calc R U . . .
C13 C 0.3602(2) 0.66695(13) 0.05690(9) 0.0328(5) Uani 1 1 d . . . . .
H13A H 0.254009 0.665713 0.051849 0.049 Uiso 1 1 calc R U . . .
H13B H 0.400823 0.619819 0.044039 0.049 Uiso 1 1 calc R U . . .
H13C H 0.399487 0.706192 0.031114 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4525(2) 0.79126(11) 0.32887(8) 0.0191(4) Uani 1 1 d . . . . .
H14A H 0.546292 0.764851 0.326325 0.023 Uiso 1 1 calc R U . . .
H14B H 0.473704 0.842297 0.341839 0.023 Uiso 1 1 calc R U . . .
C15 C 0.4279(2) 0.76051(11) 0.44117(8) 0.0216(4) Uani 1 1 d . . . . .
H15 H 0.467250 0.811328 0.446244 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3073(2) 0.75038(11) 0.48993(9) 0.0264(4) Uani 1 1 d . . . . .
H16A H 0.278646 0.698087 0.491180 0.032 Uiso 1 1 calc R U . . .
H16B H 0.347127 0.763775 0.531552 0.032 Uiso 1 1 calc R U . . .
C17 C 0.5557(2) 0.70682(11) 0.45285(9) 0.0244(4) Uani 1 1 d . . . . .
H17A H 0.636129 0.718423 0.424666 0.029 Uiso 1 1 calc R U . . .
H17B H 0.592798 0.711614 0.496246 0.029 Uiso 1 1 calc R U . . .
B1 B 0.2390(2) 0.79933(13) 0.13322(9) 0.0202(5) Uani 1 1 d . . . . .
F3 F 0.78137(13) 0.37243(6) 0.08345(5) 0.0285(3) Uani 1 1 d . . . . .
F4 F 0.58005(13) 0.44186(7) 0.10863(5) 0.0346(3) Uani 1 1 d . . . . .
O3 O 1.23244(16) 0.56622(8) 0.45978(6) 0.0251(3) Uani 1 1 d . . . . .
H3A H 1.319(3) 0.5885(16) 0.4577(13) 0.058(8) Uiso 1 1 d . . . . .
O4 O 0.75629(14) 0.54946(8) 0.45670(6) 0.0234(3) Uani 1 1 d . . . . .
H4A H 0.764(3) 0.5138(14) 0.4839(12) 0.037(7) Uiso 1 1 d . . . . .
N4 N 0.82193(18) 0.48965(9) 0.13720(7) 0.0233(4) Uani 1 1 d . . . . .
N5 N 0.71735(16) 0.38065(9) 0.19362(7) 0.0201(3) Uani 1 1 d . . . . .
N6 N 0.92424(17) 0.53902(9) 0.34507(7) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.851106 0.567144 0.333330 0.023 Uiso 1 1 calc R U . . .
C18 C 0.89146(19) 0.46422(10) 0.24734(8) 0.0184(4) Uani 1 1 d . . . . .
C19 C 0.9006(2) 0.50937(11) 0.19296(8) 0.0204(4) Uani 1 1 d . . . . .
C20 C 0.9827(2) 0.57581(11) 0.18026(9) 0.0242(4) Uani 1 1 d . . . . .
C21 C 0.9512(2) 0.59360(12) 0.11776(10) 0.0301(5) Uani 1 1 d . . . . .
H21 H 0.988481 0.634669 0.096230 0.036 Uiso 1 1 calc R U . . .
C22 C 0.8543(2) 0.54013(12) 0.09195(9) 0.0290(5) Uani 1 1 d . . . . .
C23 C 1.0847(2) 0.61888(11) 0.22352(9) 0.0276(5) Uani 1 1 d . . . . .
H23A H 1.040200 0.624179 0.264204 0.041 Uiso 1 1 calc R U . . .
H23B H 1.102091 0.667492 0.205829 0.041 Uiso 1 1 calc R U . . .
H23C H 1.177326 0.592666 0.228355 0.041 Uiso 1 1 calc R U . . .
C24 C 0.7932(3) 0.53471(14) 0.02552(10) 0.0422(6) Uani 1 1 d . . . . .
H24A H 0.827405 0.489308 0.006415 0.063 Uiso 1 1 calc R U . . .
H24B H 0.826350 0.576815 0.001401 0.063 Uiso 1 1 calc R U . . .
H24C H 0.686601 0.534513 0.026108 0.063 Uiso 1 1 calc R U . . .
C25 C 0.7980(2) 0.40194(10) 0.24845(8) 0.0188(4) Uani 1 1 d . . . . .
C26 C 0.7652(2) 0.34911(11) 0.29703(9) 0.0214(4) Uani 1 1 d . . . . .
C27 C 0.6676(2) 0.29811(11) 0.26991(9) 0.0251(4) Uani 1 1 d . . . . .
H27 H 0.626401 0.257282 0.290425 0.030 Uiso 1 1 calc R U . . .
C28 C 0.6409(2) 0.31794(11) 0.20664(9) 0.0229(4) Uani 1 1 d . . . . .
C29 C 0.8183(2) 0.34575(12) 0.36495(9) 0.0275(5) Uani 1 1 d . . . . .
H29A H 0.921733 0.332588 0.366706 0.041 Uiso 1 1 calc R U . . .
H29B H 0.762261 0.308788 0.387135 0.041 Uiso 1 1 calc R U . . .
H29C H 0.805029 0.393732 0.384472 0.041 Uiso 1 1 calc R U . . .
C30 C 0.5469(2) 0.27767(12) 0.15839(10) 0.0299(5) Uani 1 1 d . . . . .
H30A H 0.443956 0.287636 0.165795 0.045 Uiso 1 1 calc R U . . .
H30B H 0.564937 0.224862 0.161627 0.045 Uiso 1 1 calc R U . . .
H30C H 0.571257 0.294621 0.116702 0.045 Uiso 1 1 calc R U . . .
C31 C 0.9890(2) 0.48176(11) 0.30447(8) 0.0201(4) Uani 1 1 d . . . . .
H31A H 1.004886 0.436425 0.329002 0.024 Uiso 1 1 calc R U . . .
H31B H 1.084990 0.498939 0.290407 0.024 Uiso 1 1 calc R U . . .
C32 C 0.9971(2) 0.54326(11) 0.40766(8) 0.0194(4) Uani 1 1 d . . . . .
H32 H 1.011177 0.492495 0.424297 0.023 Uiso 1 1 calc R U . . .
C33 C 1.1483(2) 0.58126(11) 0.40317(9) 0.0223(4) Uani 1 1 d . . . . .
H33A H 1.200179 0.562289 0.366734 0.027 Uiso 1 1 calc R U . . .
H33B H 1.135303 0.634804 0.397980 0.027 Uiso 1 1 calc R U . . .
C34 C 0.8966(2) 0.58633(11) 0.45136(8) 0.0209(4) Uani 1 1 d . . . . .
H34A H 0.943991 0.590496 0.493027 0.025 Uiso 1 1 calc R U . . .
H34B H 0.881138 0.636453 0.434862 0.025 Uiso 1 1 calc R U . . .
B2 B 0.7218(2) 0.42053(13) 0.12841(10) 0.0221(5) 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
F1 B1 1.396(2) . ?
F2 B1 1.398(2) . ?
O1 H1 0.97(4) . ?
O1 C16 1.409(3) . ?
O2 H2 0.84(3) . ?
O2 C17 1.439(2) . ?
N1 C2 1.403(2) . ?
N1 C5 1.348(2) . ?
N1 B1 1.543(3) . ?
N2 C8 1.408(2) . ?
N2 C11 1.349(2) . ?
N2 B1 1.541(3) . ?
N3 H3 0.8600 . ?
N3 C14 1.467(2) . ?
N3 C15 1.477(2) . ?
C1 C2 1.401(3) . ?
C1 C8 1.401(3) . ?
C1 C14 1.510(2) . ?
C2 C3 1.431(3) . ?
C3 C4 1.382(3) . ?
C3 C6 1.499(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C5 C7 1.493(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.432(3) . ?
C9 C10 1.379(3) . ?
C9 C12 1.503(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.398(3) . ?
C11 C13 1.491(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9800 . ?
C15 C16 1.524(3) . ?
C15 C17 1.514(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
F3 B2 1.396(2) . ?
F4 B2 1.386(2) . ?
O3 H3A 0.88(3) . ?
O3 C33 1.424(2) . ?
O4 H4A 0.86(3) . ?
O4 C34 1.432(2) . ?
N4 C19 1.403(2) . ?
N4 C22 1.350(3) . ?
N4 B2 1.538(3) . ?
N5 C25 1.403(2) . ?
N5 C28 1.347(2) . ?
N5 B2 1.550(3) . ?
N6 H6 0.8600 . ?
N6 C31 1.464(2) . ?
N6 C32 1.461(2) . ?
C18 C19 1.406(3) . ?
C18 C25 1.396(3) . ?
C18 C31 1.507(3) . ?
C19 C20 1.428(3) . ?
C20 C21 1.379(3) . ?
C20 C23 1.492(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.396(3) . ?
C22 C24 1.495(3) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.429(3) . ?
C26 C27 1.381(3) . ?
C26 C29 1.500(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.396(3) . ?
C28 C30 1.493(3) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32 0.9800 . ?
C32 C33 1.526(3) . ?
C32 C34 1.516(3) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C34 H34A 0.9700 . ?
C34 H34B 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
C16 O1 H1 105(2) . . ?
C17 O2 H2 105.1(19) . . ?
C2 N1 B1 125.55(15) . . ?
C5 N1 C2 108.77(15) . . ?
C5 N1 B1 125.67(15) . . ?
C8 N2 B1 125.58(15) . . ?
C11 N2 C8 108.44(15) . . ?
C11 N2 B1 125.97(15) . . ?
C14 N3 H3 123.8 . . ?
C14 N3 C15 112.37(14) . . ?
C15 N3 H3 123.8 . . ?
C2 C1 C8 121.56(16) . . ?
C2 C1 C14 118.95(16) . . ?
C8 C1 C14 119.45(16) . . ?
N1 C2 C3 107.29(15) . . ?
C1 C2 N1 120.13(16) . . ?
C1 C2 C3 132.58(17) . . ?
C2 C3 C6 130.16(17) . . ?
C4 C3 C2 106.16(16) . . ?
C4 C3 C6 123.68(17) . . ?
C3 C4 H4 125.5 . . ?
C3 C4 C5 109.04(17) . . ?
C5 C4 H4 125.5 . . ?
N1 C5 C4 108.74(16) . . ?
N1 C5 C7 122.79(17) . . ?
C4 C5 C7 128.45(18) . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C9 107.20(15) . . ?
C1 C8 N2 119.85(16) . . ?
C1 C8 C9 132.95(17) . . ?
C8 C9 C12 130.20(17) . . ?
C10 C9 C8 106.37(16) . . ?
C10 C9 C12 123.44(18) . . ?
C9 C10 H10 125.5 . . ?
C9 C10 C11 108.98(17) . . ?
C11 C10 H10 125.5 . . ?
N2 C11 C10 109.01(16) . . ?
N2 C11 C13 123.43(18) . . ?
C10 C11 C13 127.56(18) . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C1 111.95(14) . . ?
N3 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C1 C14 H14A 109.2 . . ?
C1 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N3 C15 H15 107.3 . . ?
N3 C15 C16 109.36(15) . . ?
N3 C15 C17 113.66(15) . . ?
C16 C15 H15 107.3 . . ?
C17 C15 H15 107.3 . . ?
C17 C15 C16 111.48(15) . . ?
O1 C16 C15 112.62(16) . . ?
O1 C16 H16A 109.1 . . ?
O1 C16 H16B 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C15 108.94(15) . . ?
O2 C17 H17A 109.9 . . ?
O2 C17 H17B 109.9 . . ?
C15 C17 H17A 109.9 . . ?
C15 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
F1 B1 F2 108.90(15) . . ?
F1 B1 N1 109.96(16) . . ?
F1 B1 N2 110.32(15) . . ?
F2 B1 N1 109.99(15) . . ?
F2 B1 N2 110.35(16) . . ?
N2 B1 N1 107.31(14) . . ?
C33 O3 H3A 109.2(18) . . ?
C34 O4 H4A 109.6(17) . . ?
C19 N4 B2 125.83(15) . . ?
C22 N4 C19 108.14(16) . . ?
C22 N4 B2 125.98(16) . . ?
C25 N5 B2 125.61(16) . . ?
C28 N5 C25 108.34(15) . . ?
C28 N5 B2 125.98(16) . . ?
C31 N6 H6 123.6 . . ?
C32 N6 H6 123.6 . . ?
C32 N6 C31 112.80(14) . . ?
C19 C18 C31 119.21(17) . . ?
C25 C18 C19 121.22(17) . . ?
C25 C18 C31 119.52(16) . . ?
N4 C19 C18 120.06(17) . . ?
N4 C19 C20 107.76(16) . . ?
C18 C19 C20 132.15(18) . . ?
C19 C20 C23 128.92(17) . . ?
C21 C20 C19 105.99(17) . . ?
C21 C20 C23 125.08(18) . . ?
C20 C21 H21 125.5 . . ?
C20 C21 C22 109.09(18) . . ?
C22 C21 H21 125.5 . . ?
N4 C22 C21 109.00(17) . . ?
N4 C22 C24 122.54(19) . . ?
C21 C22 C24 128.45(19) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C26 107.44(16) . . ?
C18 C25 N5 120.18(16) . . ?
C18 C25 C26 132.36(17) . . ?
C25 C26 C29 130.10(18) . . ?
C27 C26 C25 106.24(17) . . ?
C27 C26 C29 123.65(18) . . ?
C26 C27 H27 125.6 . . ?
C26 C27 C28 108.75(17) . . ?
C28 C27 H27 125.6 . . ?
N5 C28 C27 109.21(17) . . ?
N5 C28 C30 123.13(18) . . ?
C27 C28 C30 127.65(18) . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N6 C31 C18 112.33(15) . . ?
N6 C31 H31A 109.1 . . ?
N6 C31 H31B 109.1 . . ?
C18 C31 H31A 109.1 . . ?
C18 C31 H31B 109.1 . . ?
H31A C31 H31B 107.9 . . ?
N6 C32 H32 109.1 . . ?
N6 C32 C33 110.41(14) . . ?
N6 C32 C34 108.28(14) . . ?
C33 C32 H32 109.1 . . ?
C34 C32 H32 109.1 . . ?
C34 C32 C33 110.96(15) . . ?
O3 C33 C32 108.75(15) . . ?
O3 C33 H33A 109.9 . . ?
O3 C33 H33B 109.9 . . ?
C32 C33 H33A 109.9 . . ?
C32 C33 H33B 109.9 . . ?
H33A C33 H33B 108.3 . . ?
O4 C34 C32 110.76(15) . . ?
O4 C34 H34A 109.5 . . ?
O4 C34 H34B 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 108.1 . . ?
F3 B2 N4 110.03(16) . . ?
F3 B2 N5 109.72(16) . . ?
F4 B2 F3 109.33(16) . . ?
F4 B2 N4 110.37(17) . . ?
F4 B2 N5 110.50(16) . . ?
N4 B2 N5 106.86(15) . . ?

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
N1 C2 C3 C4 -0.02(19) . . . . ?
N1 C2 C3 C6 179.62(17) . . . . ?
N2 C8 C9 C10 0.3(2) . . . . ?
N2 C8 C9 C12 -179.57(18) . . . . ?
N3 C15 C16 O1 -47.4(2) . . . . ?
N3 C15 C17 O2 -57.58(19) . . . . ?
C1 C2 C3 C4 179.10(19) . . . . ?
C1 C2 C3 C6 -1.3(3) . . . . ?
C1 C8 C9 C10 -178.86(19) . . . . ?
C1 C8 C9 C12 1.3(3) . . . . ?
C2 N1 C5 C4 -0.8(2) . . . . ?
C2 N1 C5 C7 177.94(16) . . . . ?
C2 N1 B1 F1 -118.76(18) . . . . ?
C2 N1 B1 F2 121.31(17) . . . . ?
C2 N1 B1 N2 1.2(2) . . . . ?
C2 C1 C8 N2 1.8(3) . . . . ?
C2 C1 C8 C9 -179.16(18) . . . . ?
C2 C1 C14 N3 84.9(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 N1 0.8(2) . . . . ?
C3 C4 C5 C7 -177.85(18) . . . . ?
C5 N1 C2 C1 -178.73(16) . . . . ?
C5 N1 C2 C3 0.52(19) . . . . ?
C5 N1 B1 F1 59.6(2) . . . . ?
C5 N1 B1 F2 -60.3(2) . . . . ?
C5 N1 B1 N2 179.61(15) . . . . ?
C6 C3 C4 C5 179.86(16) . . . . ?
C8 N2 C11 C10 0.7(2) . . . . ?
C8 N2 C11 C13 -178.97(17) . . . . ?
C8 N2 B1 F1 118.81(18) . . . . ?
C8 N2 B1 F2 -120.80(18) . . . . ?
C8 N2 B1 N1 -1.0(2) . . . . ?
C8 C1 C2 N1 -1.5(3) . . . . ?
C8 C1 C2 C3 179.46(18) . . . . ?
C8 C1 C14 N3 -97.22(19) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C9 C10 C11 N2 -0.5(2) . . . . ?
C9 C10 C11 C13 179.14(19) . . . . ?
C11 N2 C8 C1 178.67(16) . . . . ?
C11 N2 C8 C9 -0.62(19) . . . . ?
C11 N2 B1 F1 -60.1(2) . . . . ?
C11 N2 B1 F2 60.3(2) . . . . ?
C11 N2 B1 N1 -179.90(16) . . . . ?
C12 C9 C10 C11 -179.99(17) . . . . ?
C14 N3 C15 C16 158.42(16) . . . . ?
C14 N3 C15 C17 -76.29(19) . . . . ?
C14 C1 C2 N1 176.32(15) . . . . ?
C14 C1 C2 C3 -2.7(3) . . . . ?
C14 C1 C8 N2 -176.05(15) . . . . ?
C14 C1 C8 C9 3.0(3) . . . . ?
C15 N3 C14 C1 -174.71(15) . . . . ?
C16 C15 C17 O2 66.57(19) . . . . ?
C17 C15 C16 O1 -173.90(16) . . . . ?
B1 N1 C2 C1 -0.1(3) . . . . ?
B1 N1 C2 C3 179.12(15) . . . . ?
B1 N1 C5 C4 -179.41(16) . . . . ?
B1 N1 C5 C7 -0.7(3) . . . . ?
B1 N2 C8 C1 -0.4(3) . . . . ?
B1 N2 C8 C9 -179.70(16) . . . . ?
B1 N2 C11 C10 179.79(16) . . . . ?
B1 N2 C11 C13 0.1(3) . . . . ?
N4 C19 C20 C21 -0.1(2) . . . . ?
N4 C19 C20 C23 -179.38(18) . . . . ?
N5 C25 C26 C27 0.3(2) . . . . ?
N5 C25 C26 C29 -178.78(18) . . . . ?
N6 C32 C33 O3 -164.03(15) . . . . ?
N6 C32 C34 O4 60.15(19) . . . . ?
C18 C19 C20 C21 178.0(2) . . . . ?
C18 C19 C20 C23 -1.3(3) . . . . ?
C18 C25 C26 C27 -178.13(19) . . . . ?
C18 C25 C26 C29 2.8(3) . . . . ?
C19 N4 C22 C21 -1.1(2) . . . . ?
C19 N4 C22 C24 177.94(19) . . . . ?
C19 N4 B2 F3 -115.55(19) . . . . ?
C19 N4 B2 F4 123.70(18) . . . . ?
C19 N4 B2 N5 3.5(2) . . . . ?
C19 C18 C25 N5 3.8(3) . . . . ?
C19 C18 C25 C26 -177.94(18) . . . . ?
C19 C18 C31 N6 84.5(2) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C20 C21 C22 N4 1.1(2) . . . . ?
C20 C21 C22 C24 -177.9(2) . . . . ?
C22 N4 C19 C18 -177.59(17) . . . . ?
C22 N4 C19 C20 0.8(2) . . . . ?
C22 N4 B2 F3 61.5(2) . . . . ?
C22 N4 B2 F4 -59.2(2) . . . . ?
C22 N4 B2 N5 -179.41(17) . . . . ?
C23 C20 C21 C22 178.75(19) . . . . ?
C25 N5 C28 C27 1.1(2) . . . . ?
C25 N5 C28 C30 -177.64(17) . . . . ?
C25 N5 B2 F3 115.57(19) . . . . ?
C25 N5 B2 F4 -123.81(18) . . . . ?
C25 N5 B2 N4 -3.7(2) . . . . ?
C25 C18 C19 N4 -3.9(3) . . . . ?
C25 C18 C19 C20 178.18(19) . . . . ?
C25 C18 C31 N6 -97.96(19) . . . . ?
C25 C26 C27 C28 0.4(2) . . . . ?
C26 C27 C28 N5 -0.9(2) . . . . ?
C26 C27 C28 C30 177.77(18) . . . . ?
C28 N5 C25 C18 177.78(16) . . . . ?
C28 N5 C25 C26 -0.90(19) . . . . ?
C28 N5 B2 F3 -61.3(2) . . . . ?
C28 N5 B2 F4 59.3(2) . . . . ?
C28 N5 B2 N4 179.42(16) . . . . ?
C29 C26 C27 C28 179.53(17) . . . . ?
C31 N6 C32 C33 74.64(19) . . . . ?
C31 N6 C32 C34 -163.70(15) . . . . ?
C31 C18 C19 N4 173.60(15) . . . . ?
C31 C18 C19 C20 -4.3(3) . . . . ?
C31 C18 C25 N5 -173.78(15) . . . . ?
C31 C18 C25 C26 4.5(3) . . . . ?
C32 N6 C31 C18 165.58(15) . . . . ?
C33 C32 C34 O4 -178.53(15) . . . . ?
C34 C32 C33 O3 75.91(19) . . . . ?
B2 N4 C19 C18 -0.1(3) . . . . ?
B2 N4 C19 C20 178.27(17) . . . . ?
B2 N4 C22 C21 -178.62(18) . . . . ?
B2 N4 C22 C24 0.4(3) . . . . ?
B2 N5 C25 C18 0.4(3) . . . . ?
B2 N5 C25 C26 -178.24(16) . . . . ?
B2 N5 C28 C27 178.46(16) . . . . ?
B2 N5 C28 C30 -0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.615
_oxdiff_exptl_absorpt_empirical_full_min 0.706
