# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_exp_4444
_audit_block_doi                 10.5517/ccdc.csd.cc1ywxwm
_database_code_depnum_ccdc_archive 'CCDC 1814302'
_audit_update_record             
;
2018-01-02 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2018-01-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C23 H19 B N2'
_chemical_formula_sum            'C23 H19 B N2'
_chemical_formula_weight         334.24
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
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'
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'
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                   9.5765(11)
_cell_length_b                   10.1909(12)
_cell_length_c                   10.8774(16)
_cell_angle_alpha                115.915(13)
_cell_angle_beta                 106.476(11)
_cell_angle_gamma                90.377(10)
_cell_volume                     905.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1410
_cell_measurement_temperature    294.29(18)
_cell_measurement_theta_max      27.0320
_cell_measurement_theta_min      3.4200
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2264
_exptl_crystal_description       block
_exptl_crystal_F_000             352.1254
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7397
_diffrn_reflns_theta_full        24.9967
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.93
_diffrn_ambient_temperature      294.29(18)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.9984
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0729373000
_diffrn_orient_matrix_UB_12      0.0161726000
_diffrn_orient_matrix_UB_13      -0.0070460000
_diffrn_orient_matrix_UB_21      0.0253277000
_diffrn_orient_matrix_UB_22      0.0743022000
_diffrn_orient_matrix_UB_23      0.0200210000
_diffrn_orient_matrix_UB_31      -0.0120113000
_diffrn_orient_matrix_UB_32      -0.0186017000
_diffrn_orient_matrix_UB_33      -0.0734787000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              10
_reflns_limit_k_min              -12
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1860
_reflns_number_total             3178
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.5462
_refine_diff_density_min         -0.4756
_refine_diff_density_rms         0.0651
_refine_ls_d_res_high            0.8410
_refine_ls_d_res_low             6.9611
_refine_ls_goodness_of_fit_ref   1.0571
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3178
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1046
_refine_ls_R_factor_gt           0.0612
_refine_ls_restrained_S_all      1.0559
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0808P)²+0.0198P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.1903
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid bond restraints
 C3, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3. Uiso/Uaniso restraints and constraints
C3 \\sim C16: within 1.7A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C6(H6), C7(H7), C9(H9), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23),
  C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_primary     iterative
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
_atom_site_refinement_flags_adp
N1 N 0.2348(2) 0.2219(3) 0.2851(2) 0.0544(7) Uani 1.000000 . .
C2 C 0.2493(2) 0.1982(3) 0.5195(2) 0.0421(7) Uani 1.000000 . .
C3 C 0.1566(2) -0.0314(3) 0.2598(3) 0.0448(6) Uani 1.000000 . U
N4 N 0.1786(2) 0.0061(3) 0.0660(2) 0.0625(8) Uani 1.000000 . .
H4 H 0.1554(2) -0.0304(3) -0.0262(2) 0.0750(9) Uiso 1.000000 R .
C5 C 0.1591(2) -0.0892(3) 0.1211(3) 0.0523(8) Uani 1.000000 . .
C6 C -0.1263(3) 0.0720(3) 0.3085(3) 0.0570(8) Uani 1.000000 . .
H6 H -0.1042(3) -0.0186(3) 0.3035(3) 0.0684(10) Uiso 1.000000 R .
C7 C 0.3941(3) 0.1723(3) 0.5583(3) 0.0558(8) Uani 1.000000 . .
H7 H 0.4350(3) 0.1216(3) 0.4857(3) 0.0670(10) Uiso 1.000000 R .
C8 C -0.0143(3) 0.1734(3) 0.3287(2) 0.0431(7) Uani 1.000000 . .
C9 C 0.2979(3) 0.3686(3) 0.3632(3) 0.0570(8) Uani 1.000000 . .
H9 H 0.3047(3) 0.4175(3) 0.4601(3) 0.0685(10) Uiso 1.000000 R .
C10 C 0.2313(3) 0.1521(3) 0.1447(3) 0.0500(8) Uani 1.000000 . .
C11 C 0.2809(3) 0.3230(3) 0.7751(3) 0.0644(9) Uani 1.000000 . .
H11 H 0.2416(3) 0.3749(3) 0.8487(3) 0.0773(11) Uiso 1.000000 R .
C12 C 0.1955(3) 0.2745(3) 0.6319(3) 0.0518(8) Uani 1.000000 . .
H12 H 0.0993(3) 0.2942(3) 0.6115(3) 0.0621(9) Uiso 1.000000 R .
C13 C 0.4219(3) 0.2943(3) 0.8075(3) 0.0628(9) Uani 1.000000 . .
H13 H 0.4790(3) 0.3263(3) 0.9031(3) 0.0753(10) Uiso 1.000000 R .
C14 C 0.4789(3) 0.2184(3) 0.6988(3) 0.0622(9) Uani 1.000000 . .
H14 H 0.5749(3) 0.1981(3) 0.7200(3) 0.0746(11) Uiso 1.000000 R .
C15 C -0.0569(3) 0.3049(3) 0.3352(3) 0.0612(8) Uani 1.000000 . .
H15 H 0.0140(3) 0.3774(3) 0.3492(3) 0.0734(10) Uiso 1.000000 R .
C16 C 0.1423(2) -0.1293(3) 0.3113(3) 0.0510(6) Uani 1.000000 . U
H16 H 0.1419(2) -0.0922(3) 0.4060(3) 0.0611(7) Uiso 1.000000 R .
C17 C -0.2699(3) 0.1000(4) 0.2956(3) 0.0737(10) Uani 1.000000 . .
H17 H -0.3416(3) 0.0287(4) 0.2821(3) 0.0885(12) Uiso 1.000000 R .
C18 C -0.3066(3) 0.2314(4) 0.3025(3) 0.0699(10) Uani 1.000000 . .
H18 H -0.4027(3) 0.2506(4) 0.2942(3) 0.0839(12) Uiso 1.000000 R .
C19 C 0.1465(3) -0.2415(4) 0.0380(3) 0.0712(11) Uani 1.000000 . .
H19 H 0.1497(3) -0.2788(4) -0.0558(3) 0.0854(13) Uiso 1.000000 R .
B20 B 0.1557(3) 0.1415(3) 0.3515(3) 0.0431(8) Uani 1.000000 . .
C21 C -0.2001(3) 0.3343(4) 0.3217(3) 0.0726(10) Uani 1.000000 . .
H21 H -0.2235(3) 0.4242(4) 0.3259(3) 0.0872(12) Uiso 1.000000 R .
C22 C 0.2825(3) 0.2290(4) 0.0832(3) 0.0706(10) Uani 1.000000 . .
H22 H 0.2769(3) 0.1802(4) -0.0134(3) 0.0847(12) Uiso 1.000000 R .
C23 C 0.3502(3) 0.4449(4) 0.3062(4) 0.0702(9) Uani 1.000000 . .
H23 H 0.3922(3) 0.5435(4) 0.3632(4) 0.0842(11) Uiso 1.000000 R .
C24 C 0.1283(3) -0.2801(4) 0.2313(4) 0.0746(10) Uani 1.000000 . .
H24 H 0.1180(3) -0.3429(4) 0.2706(4) 0.0895(12) Uiso 1.000000 R .
C25 C 0.1300(3) -0.3351(4) 0.0915(4) 0.0817(12) Uani 1.000000 . .
H25 H 0.1197(3) -0.4364(4) 0.0344(4) 0.0980(15) Uiso 1.000000 R .
C26 C 0.3405(3) 0.3744(4) 0.1626(4) 0.0769(10) Uani 1.000000 . .
H26 H 0.3731(3) 0.4256(4) 0.1206(4) 0.0923(12) 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
N1 C9 1.381(4) . ?
N1 C10 1.364(3) . ?
N1 B20 1.608(4) . ?
C2 C7 1.393(3) . ?
C2 C12 1.377(3) . ?
C2 B20 1.618(3) . ?
C3 C5 1.367(4) . ?
C3 C16 1.364(4) . ?
C3 B20 1.603(4) . ?
N4 C5 1.381(4) . ?
N4 C10 1.354(4) . ?
C5 C19 1.396(4) . ?
C6 C8 1.386(4) . ?
C6 C17 1.387(4) . ?
C7 C14 1.370(3) . ?
C8 C15 1.381(4) . ?
C8 B20 1.633(3) . ?
C9 C23 1.353(4) . ?
C10 C22 1.393(4) . ?
C11 C12 1.393(3) . ?
C11 C13 1.363(4) . ?
C13 C14 1.367(4) . ?
C15 C21 1.386(4) . ?
C16 C24 1.378(4) . ?
C17 C18 1.362(5) . ?
C18 C21 1.362(5) . ?
C19 C25 1.346(5) . ?
C22 C26 1.360(5) . ?
C23 C26 1.379(4) . ?
C24 C25 1.376(5) . ?

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
C10 N1 C9 116.7(3) . . ?
B20 N1 C9 121.7(2) . . ?
B20 N1 C10 121.4(2) . . ?
C12 C2 C7 115.7(2) . . ?
B20 C2 C7 120.3(2) . . ?
B20 C2 C12 124.0(2) . . ?
C16 C3 C5 116.7(3) . . ?
B20 C3 C5 121.2(3) . . ?
B20 C3 C16 121.8(2) . . ?
C10 N4 C5 125.6(2) . . ?
N4 C5 C3 118.7(3) . . ?
C19 C5 C3 120.7(4) . . ?
C19 C5 N4 120.6(3) . . ?
C17 C6 C8 122.7(3) . . ?
C14 C7 C2 122.9(2) . . ?
C15 C8 C6 114.7(2) . . ?
B20 C8 C6 121.9(3) . . ?
B20 C8 C15 123.3(3) . . ?
C23 C9 N1 123.5(3) . . ?
N4 C10 N1 119.0(3) . . ?
C22 C10 N1 120.7(3) . . ?
C22 C10 N4 120.3(3) . . ?
C13 C11 C12 120.0(2) . . ?
C11 C12 C2 122.0(2) . . ?
C14 C13 C11 119.6(2) . . ?
C13 C14 C7 119.8(2) . . ?
C21 C15 C8 123.3(3) . . ?
C24 C16 C3 123.8(3) . . ?
C18 C17 C6 120.4(3) . . ?
C21 C18 C17 118.9(3) . . ?
C25 C19 C5 121.0(3) . . ?
C2 B20 N1 109.2(2) . . ?
C3 B20 N1 105.6(2) . . ?
C3 B20 C2 110.7(2) . . ?
C8 B20 N1 109.3(2) . . ?
C8 B20 C2 112.51(19) . . ?
C8 B20 C3 109.35(19) . . ?
C18 C21 C15 120.0(3) . . ?
C26 C22 C10 120.9(3) . . ?
C26 C23 C9 119.1(3) . . ?
C25 C24 C16 118.2(4) . . ?
C24 C25 C19 119.6(3) . . ?
C23 C26 C22 119.0(3) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.670
_oxdiff_exptl_absorpt_empirical_full_min 0.365
loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C3 C16 0.0010 0.0598 -0.0020

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C3 C16 0.0010

####################################################################### 
# 
# 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_exp_4916
_audit_block_doi                 10.5517/ccdc.csd.cc1z087h
_database_code_depnum_ccdc_archive 'CCDC 1817506'
_audit_update_record             
;
2018-01-17 deposited with the CCDC.
2018-08-13 downloaded from the CCDC.
;
_audit_creation_date             2018-01-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C17 H14 B F N2'
_chemical_formula_sum            'C17 H14 B F N2'
_chemical_formula_weight         276.14
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
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'
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'
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      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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.1839(14)
_cell_length_b                   11.2820(14)
_cell_length_c                   14.148(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.510(17)
_cell_angle_gamma                90
_cell_volume                     1436.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1695
_cell_measurement_temperature    296.2(2)
_cell_measurement_theta_max      27.3250
_cell_measurement_theta_min      4.2300
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_description       block
_exptl_crystal_density_diffrn    1.2767
_exptl_crystal_F_000             576.2568
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6538
_diffrn_reflns_theta_full        24.9992
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.2(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9972
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0692810000
_diffrn_orient_matrix_UB_12      -0.0018336000
_diffrn_orient_matrix_UB_13      -0.0328202000
_diffrn_orient_matrix_UB_21      0.0144706000
_diffrn_orient_matrix_UB_22      0.0566198000
_diffrn_orient_matrix_UB_23      -0.0179050000
_diffrn_orient_matrix_UB_31      0.0345816000
_diffrn_orient_matrix_UB_32      -0.0274043000
_diffrn_orient_matrix_UB_33      -0.0349114000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                1605
_reflns_number_total             2524
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.2612
_refine_diff_density_min         -0.2862
_refine_diff_density_rms         0.0724
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.9125
_refine_ls_goodness_of_fit_ref   1.0223
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_refine_ls_number_parameters     189
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.0223
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1224
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_primary     iterative
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 0.35585(14) 0.14558(11) 0.66632(9) 0.0557(4) Uani 1.000000 .
N2 N 0.20031(19) 0.31415(15) 0.60442(13) 0.0405(5) Uani 1.000000 .
N3 N 0.2349(2) 0.45136(16) 0.73055(13) 0.0453(5) Uani 1.000000 .
H3 H 0.1950(2) 0.50251(16) 0.76259(13) 0.0544(6) Uiso 1.000000 R
C4 C 0.4576(2) 0.34652(18) 0.71468(14) 0.0365(5) Uani 1.000000 .
C5 C 0.4384(2) 0.26081(19) 0.53596(14) 0.0360(5) Uani 1.000000 .
C6 C 0.3884(2) 0.43228(19) 0.76072(14) 0.0382(5) Uani 1.000000 .
C7 C 0.4826(3) 0.3534(2) 0.38905(18) 0.0607(7) Uani 1.000000 .
H7 H 0.4672(3) 0.4168(2) 0.34619(18) 0.0728(9) Uiso 1.000000 R
C8 C 0.6108(3) 0.3364(2) 0.74661(16) 0.0537(7) Uani 1.000000 .
H8 H 0.6614(3) 0.2799(2) 0.71775(16) 0.0644(8) Uiso 1.000000 R
C9 C 0.1441(2) 0.3975(2) 0.65641(16) 0.0410(6) Uani 1.000000 .
C10 C 0.5251(2) 0.1666(2) 0.51610(16) 0.0439(6) Uani 1.000000 .
H10 H 0.5408(2) 0.1025(2) 0.55824(16) 0.0527(7) Uiso 1.000000 R
C11 C -0.0982(3) 0.3732(3) 0.5587(2) 0.0665(8) Uani 1.000000 .
H11 H -0.1990(3) 0.3911(3) 0.5446(2) 0.0798(10) Uiso 1.000000 R
C12 C 0.5675(3) 0.2587(3) 0.37199(17) 0.0550(7) Uani 1.000000 .
H12 H 0.6104(3) 0.2579(3) 0.31775(17) 0.0661(8) Uiso 1.000000 R
C13 C -0.0080(3) 0.4274(2) 0.63327(19) 0.0565(7) Uani 1.000000 .
H13 H -0.0461(3) 0.4843(2) 0.66928(19) 0.0678(8) Uiso 1.000000 R
B14 B 0.3682(3) 0.2655(2) 0.63120(18) 0.0375(6) Uani 1.000000 .
C15 C 0.5888(2) 0.1657(2) 0.43500(17) 0.0521(7) Uani 1.000000 .
H15 H 0.6462(2) 0.1014(2) 0.42352(17) 0.0626(8) Uiso 1.000000 R
C16 C 0.4664(3) 0.5028(2) 0.83474(16) 0.0530(7) Uani 1.000000 .
H16 H 0.4164(3) 0.5586(2) 0.86473(16) 0.0636(8) Uiso 1.000000 R
C17 C 0.4196(3) 0.3542(2) 0.47076(17) 0.0516(7) Uani 1.000000 .
H17 H 0.3632(3) 0.4192(2) 0.48199(17) 0.0620(8) Uiso 1.000000 R
C18 C 0.6907(3) 0.4056(3) 0.81862(17) 0.0643(8) Uani 1.000000 .
H18 H 0.7930(3) 0.3964(3) 0.83731(17) 0.0771(9) Uiso 1.000000 R
C19 C 0.1059(3) 0.2638(2) 0.52770(17) 0.0508(6) Uani 1.000000 .
H19 H 0.1444(3) 0.2083(2) 0.49066(17) 0.0609(7) Uiso 1.000000 R
C20 C -0.0403(3) 0.2905(2) 0.50305(19) 0.0625(7) Uani 1.000000 .
H20 H -0.1007(3) 0.2546(2) 0.45024(19) 0.0750(9) Uiso 1.000000 R
C21 C 0.6166(3) 0.4894(2) 0.86297(17) 0.0640(7) Uani 1.000000 .
H21 H 0.6692(3) 0.5365(2) 0.91205(17) 0.0768(9) 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 B14 1.453(3) . ?
N2 C9 1.357(3) . ?
N2 B14 1.609(3) . ?
N2 C19 1.370(3) . ?
N3 C6 1.405(3) . ?
N3 C9 1.348(3) . ?
C4 C6 1.389(3) . ?
C4 C8 1.394(3) . ?
C4 B14 1.587(3) . ?
C5 C10 1.389(3) . ?
C5 B14 1.607(3) . ?
C5 C17 1.388(3) . ?
C6 C16 1.394(3) . ?
C7 C12 1.372(3) . ?
C7 C17 1.393(3) . ?
C8 C18 1.374(3) . ?
C9 C13 1.411(3) . ?
C10 C15 1.388(3) . ?
C11 C13 1.350(3) . ?
C11 C20 1.393(4) . ?
C12 C15 1.366(3) . ?
C16 C21 1.366(3) . ?
C18 C21 1.386(3) . ?
C19 C20 1.352(3) . ?

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
B14 N2 C9 123.98(18) . . ?
C19 N2 C9 117.88(19) . . ?
C19 N2 B14 118.04(18) . . ?
C9 N3 C6 126.49(18) . . ?
C8 C4 C6 115.6(2) . . ?
B14 C4 C6 122.21(19) . . ?
B14 C4 C8 122.19(19) . . ?
B14 C5 C10 122.45(19) . . ?
C17 C5 C10 116.53(18) . . ?
C17 C5 B14 120.98(18) . . ?
C4 C6 N3 119.3(2) . . ?
C16 C6 N3 118.4(2) . . ?
C16 C6 C4 122.3(2) . . ?
C17 C7 C12 119.8(2) . . ?
C18 C8 C4 123.3(2) . . ?
N3 C9 N2 119.41(19) . . ?
C13 C9 N2 120.4(2) . . ?
C13 C9 N3 120.2(2) . . ?
C15 C10 C5 121.7(2) . . ?
C20 C11 C13 120.1(2) . . ?
C15 C12 C7 119.7(2) . . ?
C11 C13 C9 119.8(2) . . ?
N2 B14 F1 105.16(16) . . ?
C4 B14 F1 110.24(18) . . ?
C4 B14 N2 107.92(17) . . ?
C5 B14 F1 109.16(17) . . ?
C5 B14 N2 109.87(17) . . ?
C5 B14 C4 114.11(17) . . ?
C12 C15 C10 120.3(2) . . ?
C21 C16 C6 119.6(2) . . ?
C7 C17 C5 122.0(2) . . ?
C21 C18 C8 119.0(2) . . ?
C20 C19 N2 123.4(2) . . ?
C19 C20 C11 118.4(2) . . ?
C18 C21 C16 120.1(2) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.735
_oxdiff_exptl_absorpt_empirical_full_min 0.600
