# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1518524'
_audit_update_record             
;
2017-12-17 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-12-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         'C22 H17 B F2 N4 O2'
_chemical_formula_sum            'C22 H17 B F2 N4 O2'
_chemical_formula_weight         418.23
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   7.2565(5)
_cell_length_b                   7.8314(5)
_cell_length_c                   17.8401(11)
_cell_angle_alpha                101.755(2)
_cell_angle_beta                 93.007(2)
_cell_angle_gamma                101.674(2)
_cell_volume                     967.38(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.87
_cell_measurement_theta_min      2.55
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.958
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.4356
_exptl_crystal_description       Needle
_exptl_crystal_F_000             432.2377
_exptl_crystal_recrystallization_method DCM/Hexane
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40025
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      293.0
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -10
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                3201
_reflns_number_total             4493
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         0.2807
_refine_diff_density_min         -0.2312
_refine_diff_density_rms         0.0581
_refine_ls_d_res_high            0.7673
_refine_ls_d_res_low             6.4074
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0797
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4493
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.0797
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0407P)²+0.2541P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1102
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Me refined with riding coordinates:
 C22(H22a,H22b,H22c)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C17(H17), C3(H3), C20(H20), C13(H13), C21(H21), C7(H7), C14(H14),
 C18(H18), C9(H9), C1(H1a), C2(H2), C8(H8)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
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_refinement_flags_posn
F1 F 0.86481(13) 0.85485(13) 0.09856(6) 0.0551(3) Uani 1.000000 .
O1 O 0.67985(14) 1.34840(16) 0.31006(6) 0.0498(3) Uani 1.000000 .
H1 H 0.7195(8) 1.424(2) 0.3497(7) 0.0747(5) Uiso 1.000000 GR
N3 N 0.47951(19) 1.58578(17) 0.40579(7) 0.0403(3) Uani 1.000000 .
N2 N 0.53029(17) 0.82693(16) 0.10082(7) 0.0367(3) Uani 1.000000 .
N1 N 0.73300(17) 1.10017(17) 0.07843(7) 0.0380(3) Uani 1.000000 .
N4 N 0.65168(19) 1.59282(17) 0.42485(7) 0.0404(3) Uani 1.000000 .
C11 C 0.49652(19) 1.34498(19) 0.29209(8) 0.0337(3) Uani 1.000000 .
C10 C 0.40147(19) 1.22684(19) 0.22563(8) 0.0319(3) Uani 1.000000 .
F2 F 0.69242(15) 0.82131(15) -0.01389(5) 0.0619(3) Uani 1.000000 .
C16 C 0.7375(2) 1.7258(2) 0.49015(8) 0.0390(4) Uani 1.000000 .
C4 C 0.64619(19) 1.20021(19) 0.13370(8) 0.0335(3) Uani 1.000000 .
C12 C 0.3981(2) 1.45660(19) 0.33935(8) 0.0353(3) Uani 1.000000 .
O2 O 1.0124(2) 2.11064(17) 0.67765(7) 0.0655(4) Uani 1.000000 .
C6 C 0.44435(19) 0.93163(19) 0.15460(8) 0.0341(3) Uani 1.000000 .
C15 C 0.2095(2) 1.2143(2) 0.20927(8) 0.0365(3) Uani 1.000000 .
H15 H 0.1450(2) 1.1325(2) 0.16597(8) 0.0439(4) Uiso 1.000000 R
C5 C 0.50318(19) 1.11691(19) 0.17160(8) 0.0316(3) Uani 1.000000 .
C19 C 0.9305(3) 1.9803(2) 0.61537(9) 0.0465(4) Uani 1.000000 .
C17 C 0.9256(2) 1.7362(2) 0.51067(9) 0.0452(4) Uani 1.000000 .
H17 H 0.9880(2) 1.6569(2) 0.48179(9) 0.0542(5) Uiso 1.000000 R
C3 C 0.7131(2) 1.3812(2) 0.13346(9) 0.0415(4) Uani 1.000000 .
H3 H 0.6799(2) 1.4778(2) 0.16520(9) 0.0498(4) Uiso 1.000000 R
C20 C 0.7416(3) 1.9720(2) 0.59472(10) 0.0534(4) Uani 1.000000 .
H20 H 0.6802(3) 2.0530(2) 0.62308(10) 0.0641(5) Uiso 1.000000 R
C13 C 0.2071(2) 1.4425(2) 0.31966(9) 0.0408(4) Uani 1.000000 .
H13 H 0.1424(2) 1.5169(2) 0.35018(9) 0.0490(4) Uiso 1.000000 R
C21 C 0.6444(3) 1.8463(2) 0.53327(9) 0.0471(4) Uani 1.000000 .
H21 H 0.5173(3) 1.8409(2) 0.52020(9) 0.0566(5) Uiso 1.000000 R
C7 C 0.3023(2) 0.8167(2) 0.18226(9) 0.0444(4) Uani 1.000000 .
H7 H 0.2225(2) 0.8503(2) 0.21896(9) 0.0533(5) Uiso 1.000000 R
C14 C 0.1122(2) 1.3212(2) 0.25620(9) 0.0413(4) Uani 1.000000 .
H14 H -0.0166(2) 1.3107(2) 0.24471(9) 0.0496(4) Uiso 1.000000 R
C18 C 1.0235(3) 1.8618(2) 0.57316(9) 0.0479(4) Uani 1.000000 .
H18 H 1.1503(3) 1.8666(2) 0.58665(9) 0.0575(5) Uiso 1.000000 R
C9 C 0.4439(2) 0.6567(2) 0.09586(10) 0.0473(4) Uani 1.000000 .
H9 H 0.4742(2) 0.5590(2) 0.06371(10) 0.0567(5) Uiso 1.000000 R
C1 C 0.8456(2) 1.2154(3) 0.04550(10) 0.0505(4) Uani 1.000000 .
H1a H 0.9197(2) 1.1831(3) 0.00631(10) 0.0606(5) Uiso 1.000000 R
C22 C 1.1993(3) 2.1138(3) 0.70711(11) 0.0731(6) Uani 1.000000 .
H22a H 1.2389(3) 2.2120(3) 0.75068(11) 0.1097(9) Uiso 1.000000 R
H22b H 1.2017(3) 2.0037(3) 0.72260(11) 0.1097(9) Uiso 1.000000 R
H22c H 1.2834(3) 2.1277(3) 0.66795(11) 0.1097(9) Uiso 1.000000 R
B1 B 0.7094(2) 0.8959(3) 0.06322(10) 0.0400(4) Uani 1.000000 .
C2 C 0.8359(2) 1.3896(2) 0.07806(10) 0.0513(4) Uani 1.000000 .
H2 H 0.9007(2) 1.4926(2) 0.06475(10) 0.0616(5) Uiso 1.000000 R
C8 C 0.3034(3) 0.6458(2) 0.14506(11) 0.0531(4) Uani 1.000000 .
H8 H 0.2242(3) 0.5418(2) 0.15169(11) 0.0637(5) Uiso 1.000000 R


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 1.3883(19) . ?
O1 H1 0.8200 . ?
O1 C11 1.3456(17) . ?
N3 N4 1.2647(17) . ?
N3 C12 1.4048(19) . ?
N2 C6 1.3896(18) . ?
N2 C9 1.337(2) . ?
N2 B1 1.545(2) . ?
N1 C4 1.3902(18) . ?
N1 C1 1.340(2) . ?
N1 B1 1.539(2) . ?
N4 C16 1.4132(19) . ?
C11 C10 1.395(2) . ?
C11 C12 1.4143(19) . ?
C10 C15 1.3878(19) . ?
C10 C5 1.4863(18) . ?
F2 B1 1.3691(19) . ?
C16 C17 1.376(2) . ?
C16 C21 1.399(2) . ?
C4 C5 1.393(2) . ?
C4 C3 1.403(2) . ?
C12 C13 1.388(2) . ?
O2 C19 1.3612(19) . ?
O2 C22 1.422(2) . ?
C6 C5 1.391(2) . ?
C6 C7 1.406(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.384(2) . ?
C19 C20 1.386(2) . ?
C19 C18 1.380(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.379(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.368(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(2) . ?
C21 H21 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.369(2) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C9 H9 0.9300 . ?
C9 C8 1.381(2) . ?
C1 H1a 0.9300 . ?
C1 C2 1.387(3) . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 0.9600 . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?

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
C11 O1 H1 109.5 . . ?
C12 N3 N4 115.42(12) . . ?
C9 N2 C6 107.14(13) . . ?
B1 N2 C6 125.28(12) . . ?
B1 N2 C9 127.08(13) . . ?
C1 N1 C4 107.18(13) . . ?
B1 N1 C4 124.93(12) . . ?
B1 N1 C1 127.79(13) . . ?
C16 N4 N3 116.20(12) . . ?
C10 C11 O1 118.94(12) . . ?
C12 C11 O1 121.56(12) . . ?
C12 C11 C10 119.49(12) . . ?
C15 C10 C11 119.30(12) . . ?
C5 C10 C11 121.06(12) . . ?
C5 C10 C15 119.63(12) . . ?
C17 C16 N4 116.63(14) . . ?
C21 C16 N4 124.18(14) . . ?
C21 C16 C17 119.19(14) . . ?
C5 C4 N1 120.74(13) . . ?
C3 C4 N1 107.76(13) . . ?
C3 C4 C5 131.04(13) . . ?
C11 C12 N3 124.91(13) . . ?
C13 C12 N3 115.96(13) . . ?
C13 C12 C11 119.12(13) . . ?
C22 O2 C19 118.44(15) . . ?
C5 C6 N2 120.48(13) . . ?
C7 C6 N2 107.80(13) . . ?
C7 C6 C5 131.72(13) . . ?
H15 C15 C10 119.39(8) . . ?
C14 C15 C10 121.21(14) . . ?
C14 C15 H15 119.39(9) . . ?
C4 C5 C10 119.77(13) . . ?
C6 C5 C10 119.58(12) . . ?
C6 C5 C4 120.44(13) . . ?
C20 C19 O2 115.67(15) . . ?
C18 C19 O2 124.34(16) . . ?
C18 C19 C20 119.99(15) . . ?
H17 C17 C16 119.29(9) . . ?
C18 C17 C16 121.41(15) . . ?
C18 C17 H17 119.29(10) . . ?
H3 C3 C4 126.21(9) . . ?
C2 C3 C4 107.57(15) . . ?
C2 C3 H3 126.21(10) . . ?
H20 C20 C19 119.56(9) . . ?
C21 C20 C19 120.89(16) . . ?
C21 C20 H20 119.56(10) . . ?
H13 C13 C12 119.35(8) . . ?
C14 C13 C12 121.29(13) . . ?
C14 C13 H13 119.35(8) . . ?
C20 C21 C16 119.49(16) . . ?
H21 C21 C16 120.25(9) . . ?
H21 C21 C20 120.25(10) . . ?
H7 C7 C6 126.41(9) . . ?
C8 C7 C6 107.18(14) . . ?
C8 C7 H7 126.41(10) . . ?
C13 C14 C15 119.49(13) . . ?
H14 C14 C15 120.26(9) . . ?
H14 C14 C13 120.26(8) . . ?
C17 C18 C19 119.02(16) . . ?
H18 C18 C19 120.49(10) . . ?
H18 C18 C17 120.49(10) . . ?
H9 C9 N2 124.69(9) . . ?
C8 C9 N2 110.63(15) . . ?
C8 C9 H9 124.69(10) . . ?
H1a C1 N1 124.77(9) . . ?
C2 C1 N1 110.45(14) . . ?
C2 C1 H1a 124.77(10) . . ?
H22a C22 O2 109.5 . . ?
H22b C22 O2 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 O2 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
N2 B1 F1 109.45(13) . . ?
N1 B1 F1 109.49(13) . . ?
N1 B1 N2 105.65(12) . . ?
F2 B1 F1 109.13(13) . . ?
F2 B1 N2 111.51(13) . . ?
F2 B1 N1 111.55(14) . . ?
C1 C2 C3 107.03(15) . . ?
H2 C2 C3 126.49(10) . . ?
H2 C2 C1 126.49(10) . . ?
C9 C8 C7 107.26(15) . . ?
H8 C8 C7 126.37(10) . . ?
H8 C8 C9 126.37(10) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1520438'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.10.03 svn.r3461 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 B F2 N4 O2, H2 O'
_chemical_formula_sum            'C22 H19 B F2 N4 O3'
_chemical_formula_weight         436.22
_chemical_melting_point          ?
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.3281(8)
_cell_length_b                   10.0875(13)
_cell_length_c                   31.947(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.08
_cell_angle_gamma                90
_cell_volume                     2039.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5212
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.56
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            19510
_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         26.999
_diffrn_reflns_theta_min         0.637
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4152
_reflns_number_total             4428
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.076
_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)+(0.0418P)²+0.3516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0925
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7251(9)
 0.2749(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
3.a Free rotating group:
 O3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18), C20(H20), C21(H21)
3.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
3.d Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
B1 B 0.6823(3) 0.13615(16) 0.55501(6) 0.0232(3) Uani 1 1 d . . . . .
F1 F 0.77192(18) 0.07858(10) 0.51944(3) 0.0398(3) Uani 1 1 d . . . . .
F2 F 0.57848(17) 0.03784(10) 0.57751(4) 0.0417(3) Uani 1 1 d . . . . .
C1 C 0.3595(3) 0.23587(16) 0.51639(5) 0.0264(3) Uani 1 1 d . . . . .
H1 H 0.323345 0.158381 0.501071 0.032 Uiso 1 1 calc R . . . .
C2 C 0.2481(3) 0.35543(17) 0.51496(5) 0.0282(3) Uani 1 1 d . . . . .
H2 H 0.125765 0.373601 0.498669 0.034 Uiso 1 1 calc R . . . .
C3 C 0.3495(2) 0.44214(15) 0.54173(5) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.309881 0.531271 0.547234 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5227(2) 0.37425(13) 0.55940(4) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.6769(2) 0.41539(13) 0.58792(4) 0.0170(3) Uani 1 1 d . . . . .
C6 C 0.8425(2) 0.32973(13) 0.59887(4) 0.0177(3) Uani 1 1 d . . . . .
C7 C 1.0175(2) 0.34817(14) 0.62549(5) 0.0204(3) Uani 1 1 d . . . . .
H7 H 1.048877 0.425529 0.641280 0.025 Uiso 1 1 calc R . . . .
C8 C 1.1350(2) 0.23298(15) 0.62440(5) 0.0242(3) Uani 1 1 d . . . . .
H8 H 1.262763 0.216262 0.639149 0.029 Uiso 1 1 calc R . . . .
C9 C 1.0303(2) 0.14553(15) 0.59745(5) 0.0238(3) Uani 1 1 d . . . . .
H9 H 1.076891 0.058415 0.590933 0.029 Uiso 1 1 calc R . . . .
C10 C 0.6539(2) 0.54835(13) 0.60763(4) 0.0169(3) Uani 1 1 d . . . . .
C11 C 0.4763(2) 0.57324(14) 0.63205(4) 0.0194(3) Uani 1 1 d . . . . .
H11 H 0.375448 0.504824 0.636324 0.023 Uiso 1 1 calc R . . . .
C12 C 0.4442(2) 0.69726(15) 0.65034(4) 0.0198(3) Uani 1 1 d . . . . .
C13 C 0.5908(2) 0.79746(14) 0.64317(5) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.568130 0.882818 0.654897 0.028 Uiso 1 1 calc R . . . .
C14 C 0.7688(2) 0.77476(14) 0.61927(5) 0.0225(3) Uani 1 1 d . . . . .
H14 H 0.867336 0.844287 0.614687 0.027 Uiso 1 1 calc R . . . .
C15 C 0.8042(2) 0.64994(14) 0.60183(4) 0.0181(3) Uani 1 1 d . . . . .
C16 C -0.0255(2) 0.67641(15) 0.71134(4) 0.0203(3) Uani 1 1 d . . . . .
C17 C -0.1744(2) 0.57924(14) 0.71989(5) 0.0218(3) Uani 1 1 d . . . . .
H17 H -0.161653 0.494768 0.706996 0.026 Uiso 1 1 calc R . . . .
C18 C -0.3421(2) 0.60309(15) 0.74698(5) 0.0234(3) Uani 1 1 d . . . . .
H18 H -0.442642 0.535551 0.752698 0.028 Uiso 1 1 calc R . . . .
C19 C -0.3605(2) 0.72734(15) 0.76561(4) 0.0224(3) Uani 1 1 d . . . . .
C20 C -0.2111(3) 0.82555(15) 0.75729(5) 0.0256(3) Uani 1 1 d . . . . .
H20 H -0.223509 0.909838 0.770326 0.031 Uiso 1 1 calc R . . . .
C21 C -0.0454(2) 0.80136(15) 0.73032(5) 0.0241(3) Uani 1 1 d . . . . .
H21 H 0.054909 0.869024 0.724594 0.029 Uiso 1 1 calc R . . . .
C22 C -0.6661(3) 0.66381(17) 0.80438(5) 0.0309(4) Uani 1 1 d . . . . .
H22A H -0.739532 0.631187 0.779395 0.046 Uiso 1 1 calc GR . . . .
H22B H -0.769197 0.701618 0.823887 0.046 Uiso 1 1 calc GR . . . .
H22C H -0.591663 0.590232 0.817962 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.5253(2) 0.24637(12) 0.54258(4) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.85443(19) 0.20240(11) 0.58210(4) 0.0191(2) Uani 1 1 d . . . . .
N3 N 0.2712(2) 0.73221(12) 0.67647(4) 0.0229(3) Uani 1 1 d . . . . .
N4 N 0.1439(2) 0.63957(12) 0.68424(4) 0.0211(3) Uani 1 1 d . . . . .
O1 O 0.97818(16) 0.62351(10) 0.57867(3) 0.0226(2) Uani 1 1 d . . . . .
H1A H 1.053369 0.691936 0.577031 0.034 Uiso 1 1 calc GR . . . .
O2 O -0.51768(19) 0.76326(11) 0.79261(4) 0.0287(3) Uani 1 1 d . . . . .
O3 O 1.2288(2) 0.83520(13) 0.56378(4) 0.0354(3) Uani 1 1 d . . . . .
H3A H 1.348068 0.863026 0.574133 0.053 Uiso 1 1 d G . . . .
H3B H 1.228094 0.864500 0.538202 0.053 Uiso 1 1 d G . . . .


_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
B1 F1 1.397(2) . ?
B1 F2 1.390(2) . ?
B1 N1 1.542(2) . ?
B1 N2 1.543(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.398(2) . ?
C1 N1 1.346(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.409(2) . ?
C4 C5 1.397(2) . ?
C4 N1 1.3975(18) . ?
C5 C6 1.402(2) . ?
C5 C10 1.4890(19) . ?
C6 C7 1.408(2) . ?
C6 N2 1.3937(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(2) . ?
C9 H9 0.9500 . ?
C9 N2 1.344(2) . ?
C10 C11 1.392(2) . ?
C10 C15 1.410(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.396(2) . ?
C12 C13 1.391(2) . ?
C12 N3 1.4220(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.381(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(2) . ?
C15 O1 1.3540(18) . ?
C16 C17 1.387(2) . ?
C16 C21 1.404(2) . ?
C16 N4 1.4283(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(2) . ?
C19 C20 1.395(2) . ?
C19 O2 1.3663(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C22 O2 1.425(2) . ?
N3 N4 1.2586(18) . ?
O1 H1A 0.8400 . ?
O3 H3A 0.8703 . ?
O3 H3B 0.8691 . ?

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
F1 B1 N1 110.62(13) . . ?
F1 B1 N2 110.43(14) . . ?
F2 B1 F1 108.47(13) . . ?
F2 B1 N1 110.05(14) . . ?
F2 B1 N2 110.65(13) . . ?
N2 B1 N1 106.62(11) . . ?
C2 C1 H1 124.9 . . ?
N1 C1 H1 124.9 . . ?
N1 C1 C2 110.20(13) . . ?
C1 C2 H2 126.5 . . ?
C3 C2 C1 106.99(14) . . ?
C3 C2 H2 126.5 . . ?
C2 C3 H3 126.2 . . ?
C2 C3 C4 107.51(14) . . ?
C4 C3 H3 126.2 . . ?
C5 C4 C3 131.20(13) . . ?
C5 C4 N1 121.08(13) . . ?
N1 C4 C3 107.71(12) . . ?
C4 C5 C6 120.04(13) . . ?
C4 C5 C10 118.36(12) . . ?
C6 C5 C10 121.53(12) . . ?
C5 C6 C7 131.02(13) . . ?
N2 C6 C5 120.85(13) . . ?
N2 C6 C7 108.13(12) . . ?
C6 C7 H7 126.4 . . ?
C8 C7 C6 107.28(13) . . ?
C8 C7 H7 126.4 . . ?
C7 C8 H8 126.5 . . ?
C7 C8 C9 106.96(13) . . ?
C9 C8 H8 126.5 . . ?
C8 C9 H9 124.9 . . ?
N2 C9 C8 110.29(13) . . ?
N2 C9 H9 124.9 . . ?
C11 C10 C5 118.62(12) . . ?
C11 C10 C15 119.19(13) . . ?
C15 C10 C5 122.18(13) . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 120.97(13) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 N3 125.50(13) . . ?
C13 C12 C11 118.98(13) . . ?
C13 C12 N3 115.52(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.02(14) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.14(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 119.64(13) . . ?
O1 C15 C10 118.54(12) . . ?
O1 C15 C14 121.81(13) . . ?
C17 C16 C21 119.21(14) . . ?
C17 C16 N4 116.50(13) . . ?
C21 C16 N4 124.26(14) . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.28(14) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.5 . . ?
C19 C18 C17 119.07(14) . . ?
C19 C18 H18 120.5 . . ?
C18 C19 C20 120.04(14) . . ?
O2 C19 C18 124.75(14) . . ?
O2 C19 C20 115.21(13) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.60(14) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 H21 120.1 . . ?
C20 C21 C16 119.79(15) . . ?
C20 C21 H21 120.1 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C22 H22A 109.5 . . ?
O2 C22 H22B 109.5 . . ?
O2 C22 H22C 109.5 . . ?
C1 N1 B1 127.21(13) . . ?
C1 N1 C4 107.58(12) . . ?
C4 N1 B1 125.06(12) . . ?
C6 N2 B1 125.20(12) . . ?
C9 N2 B1 127.13(12) . . ?
C9 N2 C6 107.35(12) . . ?
N4 N3 C12 115.15(12) . . ?
N3 N4 C16 114.04(12) . . ?
C15 O1 H1A 109.5 . . ?
C19 O2 C22 117.42(12) . . ?
H3A O3 H3B 104.5 . . ?

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 O3 0.84 1.87 2.7023(16) 170.1 . yes
O3 H3B F1 0.87 1.93 2.7972(17) 177.4 3_766 yes

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7251(9)
2 0.2749(9)

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1518525'
_audit_update_record             
;
2017-12-15 deposited with the CCDC.
2018-01-30 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2-dev
(compiled 2017.10.03 svn.r3461 for OlexSys, GUI svn.r5356)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 B F2 N4 O'
_chemical_formula_sum            'C22 H17 B F2 N4 O'
_chemical_formula_weight         402.20
_chemical_melting_point          ?
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'
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'

_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                   6.9013(6)
_cell_length_b                   18.4057(17)
_cell_length_c                   15.0143(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.438(3)
_cell_angle_gamma                90
_cell_volume                     1906.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5862
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            46985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2528
_reflns_number_total             4366
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4366
_refine_ls_number_restraints     183
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.4543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-C11 \\sim O1A-C11A
 with sigma of 0.02
 N3-N4 \\sim N3A-N4A
 with sigma of 0.02
 N3-C14 \\sim N3A-C14A
 with sigma of 0.02
 C22-C19 \\sim C22A-C19A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.02
 C19-C20 \\sim C19A-C20A
 with sigma of 0.02
 C18-C17 \\sim C18A-C17A
 with sigma of 0.02
 C17-C16 \\sim C17A-C16A
 with sigma of 0.02
 C16-N4 \\sim C16A-N4A
 with sigma of 0.02
 C16-C21 \\sim C16A-C21A
 with sigma of 0.02
 C14-C15 \\sim C14A-C15A
 with sigma of 0.02
 C14-C13 \\sim C14A-C13A
 with sigma of 0.02
 C15-C10 \\sim C15A-C10A
 with sigma of 0.02
 C10-C5 \\sim C10A-C5
 with sigma of 0.02
 C10-C11 \\sim C10A-C11A
 with sigma of 0.02
 C20-C21 \\sim C20A-C21A
 with sigma of 0.02
 C13-C12 \\sim C13A-C12A
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 O1-C10 \\sim O1A-C10A
 with sigma of 0.04
 O1-C12 \\sim O1A-C12A
 with sigma of 0.04
 N3-C16 \\sim N3A-C16A
 with sigma of 0.04
 N3-C15 \\sim N3A-C15A
 with sigma of 0.04
 N3-C13 \\sim N3A-C13A
 with sigma of 0.04
 C22-C18 \\sim C22A-C18A
 with sigma of 0.04
 C22-C20 \\sim C22A-C20A
 with sigma of 0.04
 C19-C17 \\sim C19A-C17A
 with sigma of 0.04
 C19-C21 \\sim C19A-C21A
 with sigma of 0.04
 C18-C16 \\sim C18A-C16A
 with sigma of 0.04
 C18-C20 \\sim C18A-C20A
 with sigma of 0.04
 C17-N4 \\sim C17A-N4A
 with sigma of 0.04
 C17-C21 \\sim C17A-C21A
 with sigma of 0.04
 C16-C20 \\sim C16A-C20A
 with sigma of 0.04
 N4-C14 \\sim N4A-C14A
 with sigma of 0.04
 N4-C21 \\sim N4A-C21A
 with sigma of 0.04
 C14-C10 \\sim C14A-C10A
 with sigma of 0.04
 C14-C12 \\sim C14A-C12A
 with sigma of 0.04
 C15-C5 \\sim C15A-C5
 with sigma of 0.04
 C15-C13 \\sim C15A-C13A
 with sigma of 0.04
 C15-C11 \\sim C15A-C11A
 with sigma of 0.04
 C10-C12 \\sim C10A-C12A
 with sigma of 0.04
 C5-C11 \\sim C5-C11A
 with sigma of 0.04
 C13-C11 \\sim C13A-C11A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C19 \\sim C19A: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C22A) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C10A) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
4. Rigid body (RIGU) restrains
 O1A, H1AA, N3A, C22A, H22D, H22E, H22F, C19A, C18A, H18A, C17A, H17A, C16A,
 N4A, C14A, C15A, H15A, C10A, C20A, H20A, C21A, H21A, C13A, H13A, C12A, H12A,
 C11A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O1A)=Sof(H1AA)=Sof(N3A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C19A)=
 Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(N4A)=Sof(C14A)=Sof(C15A)=
 Sof(H15A)=Sof(C10A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C13A)=
 Sof(H13A)=Sof(C12A)=Sof(H12A)=Sof(C11A)=1-FVAR(1)
 Sof(O1)=Sof(H1)=Sof(N3)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C19)=
 Sof(C18)=Sof(H18)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(N4)=Sof(C14)=Sof(C15)=
 Sof(H15)=Sof(C10)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C13)=Sof(H13)=
 Sof(C12)=Sof(H12)=Sof(C11)=FVAR(1)
6.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C17(H17), C15(H15), C7(H7), C8(H8), C9(H9), C20(H20), C21(H21),
 C13(H13), C12(H12), C1(H1A), C2(H2), C3(H3), C18A(H18A), C17A(H17A),
 C15A(H15A), C20A(H20A), C21A(H21A), C13A(H13A), C12A(H12A)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
6.c Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.58662(18) 0.36511(7) 0.39792(7) 0.0804(4) Uani 1 1 d . . . . .
F2 F 0.74221(18) 0.42493(6) 0.50918(9) 0.0809(4) Uani 1 1 d . . . . .
O1 O 0.8805(7) 0.1938(3) 0.7486(3) 0.0494(10) Uani 0.801(5) 1 d D . P A 1
H1 H 0.942455 0.180359 0.792912 0.074 Uiso 0.801(5) 1 calc GR . P A 1
N3 N 0.2224(3) 0.02071(13) 0.71753(15) 0.0456(7) Uani 0.801(5) 1 d D . P A 1
C6 C 0.7696(2) 0.23920(9) 0.55822(11) 0.0386(4) Uani 1 1 d . . . . .
N2 N 0.7882(2) 0.29599(8) 0.49781(9) 0.0439(4) Uani 1 1 d . . . . .
N1 N 0.4799(2) 0.34671(8) 0.54782(10) 0.0476(4) Uani 1 1 d . . . . .
C22 C -0.5711(9) -0.1490(4) 0.6368(5) 0.0657(17) Uani 0.801(5) 1 d D U P A 1
H22A H -0.542963 -0.199361 0.647401 0.098 Uiso 0.801(5) 1 calc GR . P A 1
H22B H -0.627409 -0.143302 0.578063 0.098 Uiso 0.801(5) 1 calc GR . P A 1
H22C H -0.660680 -0.131990 0.680031 0.098 Uiso 0.801(5) 1 calc GR . P A 1
C19 C -0.388(3) -0.1058(13) 0.6443(9) 0.0427(12) Uani 0.801(5) 1 d D U P A 1
C18 C -0.2534(9) -0.1120(4) 0.7141(4) 0.0496(12) Uani 0.801(5) 1 d D . P A 1
H18 H -0.273262 -0.146330 0.758469 0.060 Uiso 0.801(5) 1 calc R . P A 1
C17 C -0.0904(6) -0.0683(3) 0.7192(3) 0.0482(10) Uani 0.801(5) 1 d D . P A 1
H17 H -0.002877 -0.073049 0.766990 0.058 Uiso 0.801(5) 1 calc R . P A 1
C16 C -0.0578(5) -0.01789(19) 0.6537(2) 0.0404(8) Uani 0.801(5) 1 d D . P A 1
N4 N 0.1048(4) 0.03090(15) 0.65421(19) 0.0450(8) Uani 0.801(5) 1 d D . P A 1
C14 C 0.3849(5) 0.0685(2) 0.7211(3) 0.0396(9) Uani 0.801(5) 1 d D . P A 1
C15 C 0.4150(7) 0.1273(3) 0.6656(4) 0.0403(10) Uani 0.801(5) 1 d D . P A 1
H15 H 0.322718 0.137449 0.621135 0.048 Uiso 0.801(5) 1 calc R . P A 1
C10 C 0.5786(9) 0.1725(3) 0.6737(4) 0.0372(11) Uani 0.801(5) 1 d D . P A 1
C5 C 0.6074(2) 0.23491(9) 0.61181(10) 0.0387(4) Uani 1 1 d D . . . .
C7 C 0.9221(2) 0.19040(10) 0.54397(12) 0.0467(4) Uani 1 1 d . . . . .
H7 H 0.946783 0.147792 0.575565 0.056 Uiso 1 1 calc R . . . .
C8 C 1.0275(3) 0.21674(11) 0.47543(13) 0.0575(5) Uani 1 1 d . . . . .
H8 H 1.136173 0.195235 0.451213 0.069 Uiso 1 1 calc R . . . .
C9 C 0.9421(3) 0.28160(11) 0.44867(13) 0.0565(5) Uani 1 1 d . . . . .
H9 H 0.985908 0.310951 0.402943 0.068 Uiso 1 1 calc R . . . .
C20 C -0.3524(7) -0.0545(4) 0.5799(4) 0.0448(14) Uani 0.801(5) 1 d D . P A 1
H20 H -0.441665 -0.048465 0.533016 0.054 Uiso 0.801(5) 1 calc R . P A 1
C21 C -0.1884(6) -0.0120(3) 0.5831(3) 0.0460(9) Uani 0.801(5) 1 d D . P A 1
H21 H -0.165500 0.020809 0.537491 0.055 Uiso 0.801(5) 1 calc R . P A 1
C13 C 0.5237(5) 0.0520(2) 0.7862(3) 0.0433(8) Uani 0.801(5) 1 d D . P A 1
H13 H 0.504611 0.013265 0.824802 0.052 Uiso 0.801(5) 1 calc R . P A 1
C12 C 0.6899(8) 0.0931(4) 0.7938(4) 0.0435(10) Uani 0.801(5) 1 d D . P A 1
H12 H 0.783662 0.081326 0.836974 0.052 Uiso 0.801(5) 1 calc R . P A 1
C11 C 0.7196(15) 0.1520(7) 0.7379(8) 0.0388(12) Uani 0.801(5) 1 d D . P A 1
C4 C 0.4633(2) 0.28806(9) 0.60562(11) 0.0433(4) Uani 1 1 d . . . . .
C1 C 0.3223(3) 0.38883(11) 0.55806(14) 0.0599(6) Uani 1 1 d . . . . .
H1A H 0.297548 0.431796 0.527235 0.072 Uiso 1 1 calc R . . . .
C2 C 0.2027(3) 0.35911(11) 0.62086(15) 0.0640(6) Uani 1 1 d . . . . .
H2 H 0.085156 0.378015 0.639023 0.077 Uiso 1 1 calc R . . . .
C3 C 0.2893(3) 0.29675(10) 0.65136(13) 0.0558(5) Uani 1 1 d . . . . .
H3 H 0.241696 0.265688 0.694511 0.067 Uiso 1 1 calc R . . . .
B1 B 0.6505(3) 0.36094(12) 0.48665(15) 0.0504(6) Uani 1 1 d . . . . .
O1A O 0.863(3) 0.1891(15) 0.7518(17) 0.085(7) Uani 0.199(5) 1 d D U P A 2
H1AA H 0.945235 0.161848 0.773563 0.127 Uiso 0.199(5) 1 calc GR U P A 2
N3A N 0.1717(17) 0.0493(6) 0.6678(9) 0.051(3) Uani 0.199(5) 1 d D U P A 2
C22A C -0.556(3) -0.1620(14) 0.6238(19) 0.052(4) Uani 0.199(5) 1 d D U P A 2
H22D H -0.583327 -0.187127 0.678016 0.078 Uiso 0.199(5) 1 calc GR U P A 2
H22E H -0.519738 -0.196503 0.579171 0.078 Uiso 0.199(5) 1 calc GR U P A 2
H22F H -0.668454 -0.135723 0.603543 0.078 Uiso 0.199(5) 1 calc GR U P A 2
C19A C -0.391(11) -0.110(5) 0.641(4) 0.0427(13) Uani 0.199(5) 1 d D U P A 2
C18A C -0.307(3) -0.0629(14) 0.5785(16) 0.035(3) Uani 0.199(5) 1 d D U P A 2
H18A H -0.357722 -0.060104 0.520660 0.042 Uiso 0.199(5) 1 calc R U P A 2
C17A C -0.147(3) -0.0208(12) 0.6042(14) 0.045(3) Uani 0.199(5) 1 d D U P A 2
H17A H -0.105754 0.017163 0.568370 0.054 Uiso 0.199(5) 1 calc R U P A 2
C16A C -0.052(2) -0.0360(9) 0.6819(12) 0.043(3) Uani 0.199(5) 1 d D U P A 2
N4A N 0.1254(15) -0.0032(5) 0.7134(7) 0.053(3) Uani 0.199(5) 1 d D U P A 2
C14A C 0.351(3) 0.0810(12) 0.6940(15) 0.045(3) Uani 0.199(5) 1 d D U P A 2
C15A C 0.400(3) 0.1399(13) 0.6448(17) 0.039(3) Uani 0.199(5) 1 d D U P A 2
H15A H 0.315232 0.160239 0.602527 0.047 Uiso 0.199(5) 1 calc R U P A 2
C10A C 0.585(4) 0.1677(15) 0.662(2) 0.042(4) Uani 0.199(5) 1 d D U P A 2
C20A C -0.290(4) -0.1219(17) 0.7201(18) 0.045(3) Uani 0.199(5) 1 d D U P A 2
H20A H -0.338231 -0.155219 0.760555 0.054 Uiso 0.199(5) 1 calc R U P A 2
C21A C -0.121(3) -0.0860(13) 0.7403(15) 0.050(3) Uani 0.199(5) 1 d D U P A 2
H21A H -0.053505 -0.095667 0.793352 0.060 Uiso 0.199(5) 1 calc R U P A 2
C13A C 0.470(2) 0.0574(10) 0.7612(12) 0.046(4) Uani 0.199(5) 1 d D U P A 2
H13A H 0.432460 0.016242 0.792308 0.056 Uiso 0.199(5) 1 calc R U P A 2
C12A C 0.641(3) 0.0903(16) 0.787(2) 0.047(4) Uani 0.199(5) 1 d D U P A 2
H12A H 0.718471 0.071948 0.832896 0.057 Uiso 0.199(5) 1 calc R U P A 2
C11A C 0.694(6) 0.152(3) 0.740(3) 0.047(9) Uani 0.199(5) 1 d D U P A 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 B1 1.395(2) . ?
F2 B1 1.375(2) . ?
O1 H1 0.8200 . ?
O1 C11 1.358(4) . ?
N3 N4 1.248(4) . ?
N3 C14 1.425(4) . ?
C6 N2 1.392(2) . ?
C6 C5 1.397(2) . ?
C6 C7 1.404(2) . ?
N2 C9 1.335(2) . ?
N2 B1 1.534(3) . ?
N1 C4 1.392(2) . ?
N1 C1 1.348(2) . ?
N1 B1 1.533(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C22 C19 1.496(6) . ?
C19 C18 1.387(8) . ?
C19 C20 1.378(9) . ?
C18 H18 0.9300 . ?
C18 C17 1.383(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.376(4) . ?
C16 N4 1.437(4) . ?
C16 C21 1.377(4) . ?
C14 C15 1.385(4) . ?
C14 C13 1.385(4) . ?
C15 H15 0.9300 . ?
C15 C10 1.404(4) . ?
C10 C5 1.494(4) . ?
C10 C11 1.404(5) . ?
C5 C4 1.396(2) . ?
C5 C10A 1.459(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.364(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(3) . ?
C9 H9 0.9300 . ?
C20 H20 0.9300 . ?
C20 C21 1.376(5) . ?
C21 H21 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.376(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.389(4) . ?
C4 C3 1.408(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.368(3) . ?
C3 H3 0.9300 . ?
O1A H1AA 0.8200 . ?
O1A C11A 1.354(15) . ?
N3A N4A 1.231(13) . ?
N3A C14A 1.418(14) . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C22A C19A 1.509(17) . ?
C19A C18A 1.40(2) . ?
C19A C20A 1.39(2) . ?
C18A H18A 0.9300 . ?
C18A C17A 1.397(17) . ?
C17A H17A 0.9300 . ?
C17A C16A 1.351(15) . ?
C16A N4A 1.437(13) . ?
C16A C21A 1.365(13) . ?
C14A C15A 1.357(14) . ?
C14A C13A 1.353(13) . ?
C15A H15A 0.9300 . ?
C15A C10A 1.399(15) . ?
C10A C11A 1.398(16) . ?
C20A H20A 0.9300 . ?
C20A C21A 1.367(16) . ?
C21A H21A 0.9300 . ?
C13A H13A 0.9300 . ?
C13A C12A 1.374(15) . ?
C12A H12A 0.9300 . ?
C12A C11A 1.396(15) . ?

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
C11 O1 H1 109.5 . . ?
N4 N3 C14 115.6(3) . . ?
N2 C6 C5 120.40(14) . . ?
N2 C6 C7 107.42(14) . . ?
C5 C6 C7 131.77(16) . . ?
C6 N2 B1 126.12(15) . . ?
C9 N2 C6 107.38(14) . . ?
C9 N2 B1 126.43(16) . . ?
C4 N1 B1 125.61(14) . . ?
C1 N1 C4 107.20(16) . . ?
C1 N1 B1 127.16(17) . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
C18 C19 C22 124.1(6) . . ?
C20 C19 C22 118.4(7) . . ?
C20 C19 C18 117.4(4) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 C19 121.4(4) . . ?
C17 C18 H18 119.3 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 120.0(3) . . ?
C16 C17 H17 120.0 . . ?
C17 C16 N4 124.0(3) . . ?
C17 C16 C21 119.2(3) . . ?
C21 C16 N4 116.8(3) . . ?
N3 N4 C16 113.8(3) . . ?
C15 C14 N3 126.1(3) . . ?
C15 C14 C13 119.0(2) . . ?
C13 C14 N3 114.9(3) . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C10 122.9(3) . . ?
C10 C15 H15 118.5 . . ?
C15 C10 C5 121.4(3) . . ?
C11 C10 C15 116.2(3) . . ?
C11 C10 C5 122.2(3) . . ?
C6 C5 C10 121.5(4) . . ?
C6 C5 C10A 116.2(15) . . ?
C4 C5 C6 120.10(15) . . ?
C4 C5 C10 118.3(3) . . ?
C4 C5 C10A 123.0(14) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 C6 107.68(16) . . ?
C8 C7 H7 126.2 . . ?
C7 C8 H8 126.5 . . ?
C7 C8 C9 107.09(17) . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C8 110.43(17) . . ?
N2 C9 H9 124.8 . . ?
C8 C9 H9 124.8 . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.6(5) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.9 . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
O1 C11 C10 118.7(4) . . ?
O1 C11 C12 120.2(4) . . ?
C12 C11 C10 120.9(4) . . ?
N1 C4 C5 121.03(15) . . ?
N1 C4 C3 107.50(15) . . ?
C5 C4 C3 131.45(17) . . ?
N1 C1 H1A 124.8 . . ?
N1 C1 C2 110.36(18) . . ?
C2 C1 H1A 124.8 . . ?
C1 C2 H2 126.3 . . ?
C3 C2 C1 107.31(18) . . ?
C3 C2 H2 126.3 . . ?
C4 C3 H3 126.2 . . ?
C2 C3 C4 107.62(18) . . ?
C2 C3 H3 126.2 . . ?
F1 B1 N2 109.10(16) . . ?
F1 B1 N1 110.65(16) . . ?
F2 B1 F1 108.67(17) . . ?
F2 B1 N2 111.13(16) . . ?
F2 B1 N1 110.76(17) . . ?
N1 B1 N2 106.52(15) . . ?
C11A O1A H1AA 109.5 . . ?
N4A N3A C14A 113.9(13) . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C19A C22A H22D 109.5 . . ?
C19A C22A H22E 109.5 . . ?
C19A C22A H22F 109.5 . . ?
C18A C19A C22A 127(3) . . ?
C20A C19A C22A 113(3) . . ?
C20A C19A C18A 117.9(19) . . ?
C19A C18A H18A 120.2 . . ?
C17A C18A C19A 119.5(17) . . ?
C17A C18A H18A 120.2 . . ?
C18A C17A H17A 120.5 . . ?
C16A C17A C18A 119.0(15) . . ?
C16A C17A H17A 120.5 . . ?
C17A C16A N4A 125.9(13) . . ?
C17A C16A C21A 121.8(13) . . ?
C21A C16A N4A 112.3(13) . . ?
N3A N4A C16A 112.2(12) . . ?
C15A C14A N3A 113.7(12) . . ?
C13A C14A N3A 125.6(13) . . ?
C13A C14A C15A 120.7(13) . . ?
C14A C15A H15A 122.4 . . ?
C14A C15A C10A 115.3(13) . . ?
C10A C15A H15A 122.4 . . ?
C15A C10A C5 108.7(14) . . ?
C11A C10A C5 122.8(17) . . ?
C11A C10A C15A 123.5(18) . . ?
C19A C20A H20A 119.4 . . ?
C21A C20A C19A 121.1(17) . . ?
C21A C20A H20A 119.4 . . ?
C16A C21A C20A 119.5(16) . . ?
C16A C21A H21A 120.3 . . ?
C20A C21A H21A 120.3 . . ?
C14A C13A H13A 117.8 . . ?
C14A C13A C12A 124.3(14) . . ?
C12A C13A H13A 117.8 . . ?
C13A C12A H12A 121.4 . . ?
C13A C12A C11A 117.1(15) . . ?
C11A C12A H12A 121.4 . . ?
O1A C11A C10A 117.0(19) . . ?
O1A C11A C12A 125.2(19) . . ?
C12A C11A C10A 116.3(18) . . ?

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
N3 C14 C15 C10 179.4(7) . . . . ?
N3 C14 C13 C12 177.9(5) . . . . ?
C6 N2 C9 C8 -0.5(2) . . . . ?
C6 N2 B1 F1 -125.10(18) . . . . ?
C6 N2 B1 F2 115.10(19) . . . . ?
C6 N2 B1 N1 -5.6(2) . . . . ?
C6 C5 C4 N1 -1.3(2) . . . . ?
C6 C5 C4 C3 -179.57(17) . . . . ?
C6 C5 C10A C15A -127(2) . . . . ?
C6 C5 C10A C11A 77(5) . . . . ?
C6 C7 C8 C9 0.8(2) . . . . ?
N2 C6 C5 C10 176.7(3) . . . . ?
N2 C6 C5 C4 -0.6(2) . . . . ?
N2 C6 C5 C10A 170.4(11) . . . . ?
N2 C6 C7 C8 -1.08(19) . . . . ?
N1 C4 C3 C2 0.5(2) . . . . ?
N1 C1 C2 C3 0.5(2) . . . . ?
C22 C19 C18 C17 -177.2(17) . . . . ?
C22 C19 C20 C21 179.0(14) . . . . ?
C19 C18 C17 C16 -0.7(18) . . . . ?
C19 C20 C21 C16 -2.6(18) . . . . ?
C18 C19 C20 C21 1(3) . . . . ?
C18 C17 C16 N4 178.6(5) . . . . ?
C18 C17 C16 C21 -0.4(7) . . . . ?
C17 C16 N4 N3 4.1(5) . . . . ?
C17 C16 C21 C20 2.1(7) . . . . ?
N4 N3 C14 C15 5.3(5) . . . . ?
N4 N3 C14 C13 -173.9(3) . . . . ?
N4 C16 C21 C20 -177.0(5) . . . . ?
C14 N3 N4 C16 -179.4(3) . . . . ?
C14 C15 C10 C5 179.1(6) . . . . ?
C14 C15 C10 C11 4.2(14) . . . . ?
C14 C13 C12 C11 1.1(13) . . . . ?
C15 C14 C13 C12 -1.3(7) . . . . ?
C15 C10 C5 C6 -120.2(7) . . . . ?
C15 C10 C5 C4 57.1(9) . . . . ?
C15 C10 C11 O1 -179.8(11) . . . . ?
C15 C10 C11 C12 -4(2) . . . . ?
C10 C5 C4 N1 -178.6(3) . . . . ?
C10 C5 C4 C3 3.1(4) . . . . ?
C5 C6 N2 C9 -172.49(15) . . . . ?
C5 C6 N2 B1 4.5(2) . . . . ?
C5 C6 C7 C8 171.31(17) . . . . ?
C5 C10 C11 O1 5(2) . . . . ?
C5 C10 C11 C12 -179.2(11) . . . . ?
C5 C4 C3 C2 178.92(18) . . . . ?
C5 C10A C11A O1A -21(9) . . . . ?
C5 C10A C11A C12A 172(4) . . . . ?
C7 C6 N2 C9 0.94(18) . . . . ?
C7 C6 N2 B1 177.97(16) . . . . ?
C7 C6 C5 C10 5.1(4) . . . . ?
C7 C6 C5 C4 -172.13(17) . . . . ?
C7 C6 C5 C10A -1.2(12) . . . . ?
C7 C8 C9 N2 -0.2(2) . . . . ?
C9 N2 B1 F1 51.4(2) . . . . ?
C9 N2 B1 F2 -68.4(2) . . . . ?
C9 N2 B1 N1 170.86(16) . . . . ?
C20 C19 C18 C17 0(3) . . . . ?
C21 C16 N4 N3 -176.9(3) . . . . ?
C13 C14 C15 C10 -1.4(9) . . . . ?
C13 C12 C11 O1 177.2(11) . . . . ?
C13 C12 C11 C10 2(2) . . . . ?
C11 C10 C5 C6 54.5(12) . . . . ?
C11 C10 C5 C4 -128.2(11) . . . . ?
C4 N1 C1 C2 -0.2(2) . . . . ?
C4 N1 B1 F1 122.09(18) . . . . ?
C4 N1 B1 F2 -117.34(18) . . . . ?
C4 N1 B1 N2 3.6(2) . . . . ?
C4 C5 C10A C15A 43(3) . . . . ?
C4 C5 C10A C11A -112(5) . . . . ?
C1 N1 C4 C5 -178.80(15) . . . . ?
C1 N1 C4 C3 -0.18(19) . . . . ?
C1 N1 B1 F1 -60.1(2) . . . . ?
C1 N1 B1 F2 60.5(2) . . . . ?
C1 N1 B1 N2 -178.52(16) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
B1 N2 C9 C8 -177.47(17) . . . . ?
B1 N1 C4 C5 -0.6(2) . . . . ?
B1 N1 C4 C3 178.03(16) . . . . ?
B1 N1 C1 C2 -178.38(17) . . . . ?
N3A C14A C15A C10A -173(3) . . . . ?
N3A C14A C13A C12A -178(2) . . . . ?
C22A C19A C18A C17A -176(8) . . . . ?
C22A C19A C20A C21A 171(5) . . . . ?
C19A C18A C17A C16A 13(7) . . . . ?
C19A C20A C21A C16A 1(8) . . . . ?
C18A C19A C20A C21A 4(13) . . . . ?
C18A C17A C16A N4A 173(2) . . . . ?
C18A C17A C16A C21A -7(4) . . . . ?
C17A C16A N4A N3A 10(3) . . . . ?
C17A C16A C21A C20A 0(4) . . . . ?
N4A N3A C14A C15A -178.5(18) . . . . ?
N4A N3A C14A C13A 1(4) . . . . ?
N4A C16A C21A C20A 180(2) . . . . ?
C14A N3A N4A C16A -177.0(18) . . . . ?
C14A C15A C10A C5 -174(2) . . . . ?
C14A C15A C10A C11A -18(6) . . . . ?
C14A C13A C12A C11A 0(6) . . . . ?
C15A C14A C13A C12A 1(5) . . . . ?
C15A C10A C11A O1A -173(5) . . . . ?
C15A C10A C11A C12A 20(9) . . . . ?
C10A C5 C4 N1 -171.6(14) . . . . ?
C10A C5 C4 C3 10.2(14) . . . . ?
C20A C19A C18A C17A -12(13) . . . . ?
C21A C16A N4A N3A -169.8(18) . . . . ?
C13A C14A C15A C10A 7(4) . . . . ?
C13A C12A C11A O1A -176(6) . . . . ?
C13A C12A C11A C10A -11(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
