# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_150607c_0m
_database_code_depnum_ccdc_archive 'CCDC 1541728'
_audit_update_record             
;
2017-04-08 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H22 B F2 N3 O'
_chemical_formula_weight         369.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.8894(18)
_cell_length_b                   9.0135(12)
_cell_length_c                   31.806(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.146(2)
_cell_angle_gamma                90.00
_cell_volume                     3689.6(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6874
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      27.60

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9782
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15525
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.76
_diffrn_reflns_theta_max         27.62
_reflns_number_total             4277
_reflns_number_gt                3303
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0774P)²+1.7518P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4277
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0458
_refine_ls_wR_factor_ref         0.1441
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.078
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B -0.14305(14) 0.9785(2) 0.44639(5) 0.0387(4) Uani 1 1 d . . .
C1 C -0.09538(16) 1.2598(2) 0.50004(6) 0.0560(5) Uani 1 1 d . . .
H1A H -0.1638 1.2185 0.5010 0.084 Uiso 1 1 calc R . .
H1B H -0.0979 1.3642 0.5058 0.084 Uiso 1 1 calc R . .
H1C H -0.0497 1.2121 0.5207 0.084 Uiso 1 1 calc R . .
C2 C -0.05610(13) 1.23598(19) 0.45741(5) 0.0413(4) Uani 1 1 d . . .
C3 C 0.00449(15) 1.33269(19) 0.43452(6) 0.0471(4) Uani 1 1 d . . .
H3 H 0.0282 1.4254 0.4436 0.057 Uiso 1 1 calc R . .
C4 C 0.02330(13) 1.26860(18) 0.39654(5) 0.0409(4) Uani 1 1 d . . .
C5 C -0.02717(12) 1.12777(17) 0.39635(5) 0.0343(3) Uani 1 1 d . . .
C6 C -0.03207(11) 1.01277(16) 0.36718(4) 0.0328(3) Uani 1 1 d . . .
C7 C -0.08023(12) 0.87800(17) 0.37495(5) 0.0356(3) Uani 1 1 d . . .
C8 C -0.08823(13) 0.74280(19) 0.35171(5) 0.0415(4) Uani 1 1 d . . .
C9 C -0.13521(15) 0.6431(2) 0.37733(6) 0.0501(4) Uani 1 1 d . . .
H9 H -0.1499 0.5445 0.3707 0.060 Uiso 1 1 calc R . .
C10 C -0.15725(14) 0.7136(2) 0.41481(6) 0.0469(4) Uani 1 1 d . . .
C11 C -0.21068(19) 0.6495(2) 0.45109(7) 0.0666(6) Uani 1 1 d . . .
H11A H -0.1667 0.6592 0.4763 0.100 Uiso 1 1 calc R . .
H11B H -0.2251 0.5465 0.4458 0.100 Uiso 1 1 calc R . .
H11C H -0.2747 0.7016 0.4545 0.100 Uiso 1 1 calc R . .
C12 C 0.01298(12) 1.03660(17) 0.32494(4) 0.0340(3) Uani 1 1 d . . .
C13 C 0.08658(16) 1.3360(2) 0.36327(6) 0.0543(5) Uani 1 1 d . . .
H13A H 0.1176 1.4266 0.3737 0.081 Uiso 1 1 calc R . .
H13B H 0.0425 1.3566 0.3387 0.081 Uiso 1 1 calc R . .
H13C H 0.1402 1.2679 0.3562 0.081 Uiso 1 1 calc R . .
C14 C -0.05387(15) 0.7065(2) 0.30870(6) 0.0527(5) Uani 1 1 d . . .
H14A H 0.0203 0.6948 0.3098 0.079 Uiso 1 1 calc R . .
H14B H -0.0736 0.7855 0.2897 0.079 Uiso 1 1 calc R . .
H14C H -0.0863 0.6159 0.2990 0.079 Uiso 1 1 calc R . .
C15 C 0.11086(12) 0.97374(17) 0.31638(5) 0.0355(3) Uani 1 1 d . . .
C16 C 0.18070(13) 0.87891(18) 0.33836(5) 0.0416(4) Uani 1 1 d . . .
C17 C 0.25778(13) 0.8453(2) 0.31050(6) 0.0498(4) Uani 1 1 d . . .
H17 H 0.3147 0.7838 0.3164 0.060 Uiso 1 1 calc R . .
C18 C 0.23604(13) 0.9176(2) 0.27305(6) 0.0480(4) Uani 1 1 d . . .
C19 C 0.29337(17) 0.9198(3) 0.23341(7) 0.0717(7) Uani 1 1 d . . .
H19A H 0.2586 0.8567 0.2128 0.108 Uiso 1 1 calc R . .
H19B H 0.3630 0.8847 0.2392 0.108 Uiso 1 1 calc R . .
H19C H 0.2953 1.0193 0.2228 0.108 Uiso 1 1 calc R . .
C20 C 0.17702(16) 0.8201(2) 0.38217(6) 0.0569(5) Uani 1 1 d . . .
H20A H 0.1517 0.8959 0.4002 0.085 Uiso 1 1 calc R . .
H20B H 0.2455 0.7909 0.3923 0.085 Uiso 1 1 calc R . .
H20C H 0.1315 0.7359 0.3822 0.085 Uiso 1 1 calc R . .
F1 F -0.24677(8) 1.01871(13) 0.44427(4) 0.0590(3) Uani 1 1 d . . .
F2 F -0.11460(9) 0.92941(13) 0.48637(3) 0.0566(3) Uani 1 1 d . . .
N1 N -0.07517(10) 1.11234(14) 0.43446(4) 0.0358(3) Uani 1 1 d . . .
N2 N -0.12473(10) 0.85538(15) 0.41362(4) 0.0379(3) Uani 1 1 d . . .
N3 N 0.14751(11) 0.99476(15) 0.27669(4) 0.0402(3) Uani 1 1 d . . .
H3' H 0.1181 1.0491 0.2573 0.048 Uiso 1 1 calc R . .
O1 O -0.03929(10) 1.10974(14) 0.29879(3) 0.0468(3) 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
B1 F2 1.377(2) . ?
B1 F1 1.383(2) . ?
B1 N1 1.549(2) . ?
B1 N2 1.550(2) . ?
C1 C2 1.489(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.347(2) . ?
C2 C3 1.401(2) . ?
C3 C4 1.372(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.426(2) . ?
C4 C13 1.500(2) . ?
C5 C6 1.390(2) . ?
C5 N1 1.3978(18) . ?
C6 C7 1.392(2) . ?
C6 C12 1.5082(19) . ?
C7 N2 1.4001(18) . ?
C7 C8 1.426(2) . ?
C8 C9 1.376(2) . ?
C8 C14 1.497(2) . ?
C9 C10 1.394(2) . ?
C9 H9 0.9300 . ?
C10 N2 1.346(2) . ?
C10 C11 1.492(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 O1 1.2323(19) . ?
C12 C15 1.423(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 N3 1.3848(19) . ?
C15 C16 1.400(2) . ?
C16 C17 1.400(2) . ?
C16 C20 1.494(3) . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 N3 1.347(2) . ?
C18 C19 1.496(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N3 H3' 0.8600 . ?

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
F2 B1 F1 109.71(13) . . ?
F2 B1 N1 110.56(14) . . ?
F1 B1 N1 109.97(14) . . ?
F2 B1 N2 110.37(14) . . ?
F1 B1 N2 109.70(14) . . ?
N1 B1 N2 106.49(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 108.88(13) . . ?
N1 C2 C1 123.48(16) . . ?
C3 C2 C1 127.64(16) . . ?
C4 C3 C2 109.02(15) . . ?
C4 C3 H3 125.5 . . ?
C2 C3 H3 125.5 . . ?
C3 C4 C5 106.01(14) . . ?
C3 C4 C13 125.43(16) . . ?
C5 C4 C13 128.55(15) . . ?
C6 C5 N1 119.89(13) . . ?
C6 C5 C4 132.11(13) . . ?
N1 C5 C4 107.96(13) . . ?
C5 C6 C7 122.45(13) . . ?
C5 C6 C12 118.86(13) . . ?
C7 C6 C12 118.65(13) . . ?
C6 C7 N2 119.41(13) . . ?
C6 C7 C8 132.36(14) . . ?
N2 C7 C8 108.03(13) . . ?
C9 C8 C7 105.83(14) . . ?
C9 C8 C14 124.08(16) . . ?
C7 C8 C14 130.09(15) . . ?
C8 C9 C10 109.01(16) . . ?
C8 C9 H9 125.5 . . ?
C10 C9 H9 125.5 . . ?
N2 C10 C9 109.29(15) . . ?
N2 C10 C11 123.16(16) . . ?
C9 C10 C11 127.53(17) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 C15 122.79(13) . . ?
O1 C12 C6 117.03(13) . . ?
C15 C12 C6 120.17(13) . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C8 C14 H14A 109.5 . . ?
C8 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C8 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 C16 107.25(13) . . ?
N3 C15 C12 118.06(14) . . ?
C16 C15 C12 134.43(14) . . ?
C15 C16 C17 105.97(15) . . ?
C15 C16 C20 129.03(15) . . ?
C17 C16 C20 124.99(17) . . ?
C18 C17 C16 109.16(15) . . ?
C18 C17 H17 125.4 . . ?
C16 C17 H17 125.4 . . ?
N3 C18 C17 107.70(14) . . ?
N3 C18 C19 121.70(18) . . ?
C17 C18 C19 130.60(18) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 N1 C5 108.13(13) . . ?
C2 N1 B1 126.86(13) . . ?
C5 N1 B1 124.93(12) . . ?
C10 N2 C7 107.83(13) . . ?
C10 N2 B1 127.00(13) . . ?
C7 N2 B1 124.85(13) . . ?
C18 N3 C15 109.92(14) . . ?
C18 N3 H3' 125.0 . . ?
C15 N3 H3' 125.0 . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.62
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_150607b_0m
_database_code_depnum_ccdc_archive 'CCDC 1541729'
_audit_update_record             
;
2017-04-08 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H34 B F2 N3 O'
_chemical_formula_weight         453.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.649(3)
_cell_length_b                   9.8463(10)
_cell_length_c                   19.4482(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.3930(10)
_cell_angle_gamma                90.00
_cell_volume                     5002.5(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6599
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      25.69

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9811
_exptl_absorpt_correction_T_max  0.9852
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21129
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         27.63
_reflns_number_total             5791
_reflns_number_gt                3220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1217P)²+1.6030P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5791
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0637
_refine_ls_wR_factor_ref         0.2386
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.099
_refine_ls_shift/su_mean         0.005

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.23731(11) 0.0585(2) 0.94926(15) 0.0660(7) Uani 1 1 d . . .
F2 F 0.20871(6) 0.12201(14) 0.99266(8) 0.0815(4) Uani 1 1 d . . .
F1 F 0.21453(6) -0.06569(14) 0.92841(8) 0.0881(5) Uani 1 1 d . . .
N2 N 0.29285(7) 0.03739(17) 0.98794(10) 0.0678(5) Uani 1 1 d . . .
N1 N 0.23872(8) 0.14749(18) 0.88482(10) 0.0686(5) Uani 1 1 d . . .
O1 O 0.39520(10) 0.1187(2) 0.83721(14) 0.1298(10) Uani 1 1 d . . .
N3 N 0.38142(8) 0.4075(2) 0.94372(10) 0.0753(6) Uani 1 1 d . . .
H3 H 0.3557 0.3886 0.9626 0.090 Uiso 1 1 calc R . .
C6 C 0.33630(10) 0.0780(2) 0.96348(13) 0.0712(6) Uani 1 1 d . . .
C5 C 0.33112(10) 0.1548(2) 0.90287(13) 0.0702(6) Uani 1 1 d . . .
C4 C 0.28371(11) 0.1925(2) 0.86442(12) 0.0711(7) Uani 1 1 d . . .
C1 C 0.19816(12) 0.1971(3) 0.83957(15) 0.0818(7) Uani 1 1 d . . .
C9 C 0.30901(11) -0.0308(2) 1.04911(14) 0.0784(7) Uani 1 1 d . . .
C17 C 0.37853(11) 0.1959(3) 0.87668(15) 0.0869(8) Uani 1 1 d . . .
C2 C 0.21628(14) 0.2784(3) 0.78865(15) 0.0899(8) Uani 1 1 d . . .
C3 C 0.26857(13) 0.2752(3) 0.80355(14) 0.0845(8) Uani 1 1 d . . .
C7 C 0.38029(11) 0.0294(3) 1.01218(17) 0.0856(8) Uani 1 1 d . . .
C8 C 0.36240(12) -0.0370(3) 1.06426(18) 0.0919(8) Uani 1 1 d . . .
C14 C 0.27275(13) -0.0909(3) 1.08898(17) 0.0991(9) Uani 1 1 d . . .
H14A H 0.2562 -0.0198 1.1099 0.149 Uiso 1 1 calc R . .
H14B H 0.2910 -0.1490 1.1251 0.149 Uiso 1 1 calc R . .
H14C H 0.2475 -0.1430 1.0579 0.149 Uiso 1 1 calc R . .
C13 C 0.30185(17) 0.3492(4) 0.76226(17) 0.1202(13) Uani 1 1 d . . .
H13A H 0.2808 0.3918 0.7223 0.180 Uiso 1 1 calc R . .
H13B H 0.3247 0.2860 0.7467 0.180 Uiso 1 1 calc R . .
H13C H 0.3214 0.4171 0.7913 0.180 Uiso 1 1 calc R . .
C10 C 0.14460(13) 0.1658(4) 0.8454(2) 0.1119(11) Uani 1 1 d . . .
H10A H 0.1408 0.0695 0.8501 0.168 Uiso 1 1 calc R . .
H10B H 0.1216 0.1970 0.8041 0.168 Uiso 1 1 calc R . .
H10C H 0.1368 0.2107 0.8858 0.168 Uiso 1 1 calc R . .
C16 C 0.43508(12) 0.0418(4) 1.0056(2) 0.1182(12) Uani 1 1 d . . .
H16A H 0.4454 0.1352 1.0109 0.177 Uiso 1 1 calc R . .
H16B H 0.4388 0.0099 0.9602 0.177 Uiso 1 1 calc R . .
H16C H 0.4561 -0.0118 1.0413 0.177 Uiso 1 1 calc R . .
C11 C 0.18249(18) 0.3528(4) 0.72970(19) 0.1210(12) Uani 1 1 d . . .
H11A H 0.1496 0.3685 0.7424 0.145 Uiso 1 1 calc R . .
H11B H 0.1976 0.4407 0.7243 0.145 Uiso 1 1 calc R . .
C12 C 0.17398(17) 0.2805(4) 0.6608(2) 0.1318(13) Uani 1 1 d . . .
H12A H 0.2063 0.2660 0.6471 0.198 Uiso 1 1 calc R . .
H12B H 0.1523 0.3346 0.6259 0.198 Uiso 1 1 calc R . .
H12C H 0.1579 0.1946 0.6650 0.198 Uiso 1 1 calc R . .
C15 C 0.39466(17) -0.1079(4) 1.1268(3) 0.1372(15) Uani 1 1 d . . .
H15A H 0.3725 -0.1657 1.1480 0.165 Uiso 1 1 calc R . .
H15B H 0.4190 -0.1662 1.1101 0.165 Uiso 1 1 calc R . .
C19 C 0.44199(11) 0.3920(3) 0.87982(15) 0.0891(8) Uani 1 1 d . . .
C18 C 0.40076(11) 0.3242(3) 0.89837(14) 0.0812(7) Uani 1 1 d . . .
C21 C 0.40907(11) 0.5238(3) 0.95406(14) 0.0811(7) Uani 1 1 d . . .
C20 C 0.44699(11) 0.5157(3) 0.91441(15) 0.0905(8) Uani 1 1 d . . .
C22 C 0.39784(15) 0.6290(3) 1.00277(19) 0.1104(11) Uani 1 1 d . . .
H22A H 0.4270 0.6877 1.0156 0.166 Uiso 1 1 calc R . .
H22B H 0.3905 0.5866 1.0441 0.166 Uiso 1 1 calc R . .
H22C H 0.3688 0.6813 0.9804 0.166 Uiso 1 1 calc R . .
C25 C 0.47414(16) 0.3395(5) 0.8298(2) 0.1342(14) Uani 1 1 d . . .
H25A H 0.4802 0.2441 0.8376 0.201 Uiso 1 1 calc R . .
H25B H 0.5063 0.3867 0.8377 0.201 Uiso 1 1 calc R . .
H25C H 0.4564 0.3542 0.7824 0.201 Uiso 1 1 calc R . .
C23 C 0.48630(14) 0.6263(4) 0.9104(2) 0.1207(12) Uani 1 1 d . . .
H23A H 0.4903 0.6818 0.9523 0.145 Uiso 1 1 calc R . .
H23B H 0.5190 0.5839 0.9098 0.145 Uiso 1 1 calc R . .
C24 C 0.4727(2) 0.7148(5) 0.8487(3) 0.170(2) Uani 1 1 d . . .
H24A H 0.4668 0.6603 0.8069 0.255 Uiso 1 1 calc R . .
H24B H 0.5002 0.7770 0.8474 0.255 Uiso 1 1 calc R . .
H24C H 0.4422 0.7647 0.8514 0.255 Uiso 1 1 calc R . .
C26 C 0.4233(2) -0.0175(5) 1.1818(2) 0.1603(19) Uani 1 1 d . . .
H26A H 0.4465 0.0379 1.1621 0.240 Uiso 1 1 calc R . .
H26B H 0.4422 -0.0715 1.2192 0.240 Uiso 1 1 calc R . .
H26C H 0.3996 0.0396 1.1998 0.240 Uiso 1 1 calc R . .


_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 1.389(3) . ?
B1 F2 1.392(3) . ?
B1 N1 1.536(3) . ?
B1 N2 1.536(4) . ?
N2 C9 1.360(3) . ?
N2 C6 1.395(3) . ?
N1 C1 1.344(3) . ?
N1 C4 1.407(3) . ?
O1 C17 1.224(3) . ?
N3 C21 1.355(3) . ?
N3 C18 1.377(3) . ?
N3 H3 0.8600 . ?
C6 C5 1.384(4) . ?
C6 C7 1.436(4) . ?
C5 C4 1.386(4) . ?
C5 C17 1.508(3) . ?
C4 C3 1.428(4) . ?
C1 C2 1.430(4) . ?
C1 C10 1.486(4) . ?
C9 C8 1.396(4) . ?
C9 C14 1.477(4) . ?
C17 C18 1.423(4) . ?
C2 C3 1.366(5) . ?
C2 C11 1.501(5) . ?
C3 C13 1.498(4) . ?
C7 C8 1.368(4) . ?
C7 C16 1.496(4) . ?
C8 C15 1.514(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11 C12 1.495(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C15 C26 1.482(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C19 C20 1.385(4) . ?
C19 C18 1.393(4) . ?
C19 C25 1.509(4) . ?
C21 C20 1.389(4) . ?
C21 C22 1.474(4) . ?
C20 C23 1.524(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C23 C24 1.469(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?

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 F2 108.19(19) . . ?
F1 B1 N1 110.1(2) . . ?
F2 B1 N1 110.04(19) . . ?
F1 B1 N2 110.33(19) . . ?
F2 B1 N2 110.7(2) . . ?
N1 B1 N2 107.47(19) . . ?
C9 N2 C6 107.4(2) . . ?
C9 N2 B1 127.1(2) . . ?
C6 N2 B1 125.4(2) . . ?
C1 N1 C4 108.7(2) . . ?
C1 N1 B1 126.6(2) . . ?
C4 N1 B1 124.7(2) . . ?
C21 N3 C18 109.7(2) . . ?
C21 N3 H3 125.1 . . ?
C18 N3 H3 125.1 . . ?
C5 C6 N2 119.8(2) . . ?
C5 C6 C7 132.5(2) . . ?
N2 C6 C7 107.7(2) . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 C17 119.0(3) . . ?
C4 C5 C17 118.8(2) . . ?
C5 C4 N1 120.0(2) . . ?
C5 C4 C3 132.7(2) . . ?
N1 C4 C3 107.3(3) . . ?
N1 C1 C2 108.6(3) . . ?
N1 C1 C10 122.4(3) . . ?
C2 C1 C10 129.0(3) . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 C14 122.0(3) . . ?
C8 C9 C14 128.1(3) . . ?
O1 C17 C18 123.8(2) . . ?
O1 C17 C5 118.5(2) . . ?
C18 C17 C5 117.8(2) . . ?
C3 C2 C1 108.1(3) . . ?
C3 C2 C11 127.3(3) . . ?
C1 C2 C11 124.6(3) . . ?
C2 C3 C4 107.4(2) . . ?
C2 C3 C13 124.2(3) . . ?
C4 C3 C13 128.4(3) . . ?
C8 C7 C6 106.8(3) . . ?
C8 C7 C16 126.3(3) . . ?
C6 C7 C16 126.8(3) . . ?
C7 C8 C9 108.2(3) . . ?
C7 C8 C15 126.1(3) . . ?
C9 C8 C15 125.6(3) . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C3 C13 H13A 109.5 . . ?
C3 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C3 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12 C11 C2 114.5(3) . . ?
C12 C11 H11A 108.6 . . ?
C2 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C2 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C26 C15 C8 115.7(3) . . ?
C26 C15 H15A 108.4 . . ?
C8 C15 H15A 108.4 . . ?
C26 C15 H15B 108.4 . . ?
C8 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
C20 C19 C18 107.5(2) . . ?
C20 C19 C25 127.0(3) . . ?
C18 C19 C25 125.4(3) . . ?
N3 C18 C19 107.1(2) . . ?
N3 C18 C17 122.2(2) . . ?
C19 C18 C17 130.7(2) . . ?
N3 C21 C20 107.6(2) . . ?
N3 C21 C22 121.1(3) . . ?
C20 C21 C22 131.2(3) . . ?
C19 C20 C21 108.0(2) . . ?
C19 C20 C23 127.2(3) . . ?
C21 C20 C23 124.8(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C25 H25A 109.5 . . ?
C19 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C19 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C23 C20 113.9(3) . . ?
C24 C23 H23A 108.8 . . ?
C20 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C20 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 C26 H26A 109.5 . . ?
C15 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C15 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.63
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_131125a
_database_code_depnum_ccdc_archive 'CCDC 1901461'
loop_
_audit_author_name
_audit_author_address
'Changjiang Yu'
;Anhui Normal University
China
;
_audit_update_record             
;
2019-03-06 deposited with the CCDC.	2019-06-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_131125a             
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        505 Ang**3
RESPONSE: solvents
;
_vrf_PLAT934_131125a             
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          7 Check
RESPONSE: solvents
;
# Added during the CSD deposition process: Wednesday 06 March 2019 10:52 AM
# end Validation Reply Form

_audit_creation_date             2019-03-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H30 B F2 N3 O'
_chemical_formula_sum            'C24 H30 B F2 N3 O'
_chemical_formula_weight         425.32
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.744(3)
_cell_length_b                   12.2488(12)
_cell_length_c                   19.0154(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.276(2)
_cell_angle_gamma                90
_cell_volume                     5423.7(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6861
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.18
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9927
_exptl_absorpt_correction_T_min  0.9906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.042
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            22981
_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         27.571
_diffrn_reflns_theta_min         1.749
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_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                3679
_reflns_number_total             6276
_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       'SAINT v7.34A (Bruker, 200?)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         6276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0598
_refine_ls_restrained_S_all      1.104
_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)+(0.1282P)²+0.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2113
_refine_ls_wR_factor_ref         0.2293
_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 Secondary CH2 refined with riding coordinates:
 C00N(H00G,H00H), C00O(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 N006(H006), C00K(H00K)
2.c Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C), C00M(H00D,H00E,H00F), C00P(H00L,H00M,H00N), C00Q(H00O,
 H00P,H00Q), C00S(H00R,H00S,H00T), C00T(H00U,H00V,H00W), C00U(H00X,H00Y,H),
 C00V(H00Z,HA,HB)
;
_atom_sites_solution_hydrogens   geom
_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
F001 F 0.19413(6) 0.64701(12) 0.30315(8) 0.0786(4) Uani 1 1 d . . . . .
F002 F 0.22837(7) 0.58813(13) 0.41554(7) 0.0869(5) Uani 1 1 d . . . . .
O003 O 0.42570(6) 0.73046(15) 0.25827(8) 0.0736(5) Uani 1 1 d . . . . .
N004 N 0.27633(7) 0.73870(14) 0.37115(9) 0.0544(4) Uani 1 1 d . . . . .
N005 N 0.28355(8) 0.55052(14) 0.32517(9) 0.0571(4) Uani 1 1 d . . . . .
N006 N 0.52298(8) 0.69727(17) 0.36318(10) 0.0643(5) Uani 1 1 d . . . . .
H006 H 0.5309 0.7121 0.3220 0.077 Uiso 1 1 calc R . . . .
C007 C 0.36158(9) 0.67779(16) 0.33139(10) 0.0518(5) Uani 1 1 d . . . . .
C008 C 0.33129(8) 0.75918(16) 0.35949(10) 0.0519(5) Uani 1 1 d . . . . .
C009 C 0.46872(9) 0.68428(17) 0.37620(11) 0.0547(5) Uani 1 1 d . . . . .
C00A C 0.42098(9) 0.70038(17) 0.31882(11) 0.0561(5) Uani 1 1 d . . . . .
C00B C 0.25750(9) 0.82897(18) 0.39880(11) 0.0590(5) Uani 1 1 d . . . . .
C00C C 0.33799(9) 0.57525(17) 0.31296(10) 0.0562(5) Uani 1 1 d . . . . .
C00D C 0.47450(10) 0.66081(17) 0.44949(11) 0.0577(5) Uani 1 1 d . . . . .
C00E C 0.34617(10) 0.86900(17) 0.38131(12) 0.0604(5) Uani 1 1 d . . . . .
C00F C 0.29987(10) 0.91065(18) 0.40608(12) 0.0621(6) Uani 1 1 d . . . . .
C00G C 0.53303(10) 0.66100(17) 0.47859(12) 0.0627(6) Uani 1 1 d . . . . .
C00H C 0.35915(11) 0.48127(19) 0.28282(12) 0.0662(6) Uani 1 1 d . . . . .
C00I C 0.56204(10) 0.6836(2) 0.42388(13) 0.0682(6) Uani 1 1 d . . . . .
C00J C 0.27176(11) 0.4458(2) 0.30500(12) 0.0705(7) Uani 1 1 d . . . . .
C00K C 0.31763(12) 0.4038(2) 0.27857(13) 0.0755(7) Uani 1 1 d . . . . .
H00K H 0.3197 0.3336 0.2607 0.091 Uiso 1 1 calc R . . . .
C00L C 0.42784(11) 0.6412(2) 0.49061(12) 0.0719(6) Uani 1 1 d . . . . .
H00A H 0.4159 0.7096 0.5076 0.108 Uiso 1 1 calc GR . . . .
H00B H 0.4419 0.5945 0.5307 0.108 Uiso 1 1 calc GR . . . .
H00C H 0.3958 0.6070 0.4600 0.108 Uiso 1 1 calc GR . . . .
C00M C 0.20004(11) 0.8353(2) 0.41868(14) 0.0767(7) Uani 1 1 d . . . . .
H00D H 0.1714 0.8082 0.3798 0.115 Uiso 1 1 calc GR . . . .
H00E H 0.1916 0.9099 0.4283 0.115 Uiso 1 1 calc GR . . . .
H00F H 0.2000 0.7919 0.4607 0.115 Uiso 1 1 calc GR . . . .
C00N C 0.56189(13) 0.6484(2) 0.55609(14) 0.0819(7) Uani 1 1 d . . . . .
H00G H 0.5393 0.5995 0.5796 0.098 Uiso 1 1 calc R . . . .
H00H H 0.5994 0.6155 0.5586 0.098 Uiso 1 1 calc R . . . .
C00O C 0.29353(12) 1.02469(19) 0.43288(14) 0.0746(7) Uani 1 1 d . . . . .
H00I H 0.2677 1.0233 0.4666 0.089 Uiso 1 1 calc R . . . .
H00J H 0.3306 1.0500 0.4584 0.089 Uiso 1 1 calc R . . . .
C00P C 0.41505(13) 0.4672(2) 0.25795(15) 0.0825(8) Uani 1 1 d . . . . .
H00L H 0.4142 0.5088 0.2150 0.124 Uiso 1 1 calc GR . . . .
H00M H 0.4206 0.3914 0.2484 0.124 Uiso 1 1 calc GR . . . .
H00N H 0.4460 0.4923 0.2946 0.124 Uiso 1 1 calc GR . . . .
C00Q C 0.39989(12) 0.9278(2) 0.37673(17) 0.0863(8) Uani 1 1 d . . . . .
H00O H 0.4305 0.9017 0.4135 0.129 Uiso 1 1 calc GR . . . .
H00P H 0.3946 1.0046 0.3832 0.129 Uiso 1 1 calc GR . . . .
H00Q H 0.4093 0.9153 0.3305 0.129 Uiso 1 1 calc GR . . . .
B00R B 0.24364(11) 0.6296(2) 0.35436(13) 0.0594(6) Uani 1 1 d . . . . .
C00S C 0.21661(13) 0.3916(2) 0.31113(17) 0.0899(9) Uani 1 1 d . . . . .
H00R H 0.2118 0.3940 0.3601 0.135 Uiso 1 1 calc GR . . . .
H00S H 0.2173 0.3169 0.2960 0.135 Uiso 1 1 calc GR . . . .
H00T H 0.1852 0.4289 0.2813 0.135 Uiso 1 1 calc GR . . . .
C00T C 0.27090(15) 1.1037(3) 0.37379(17) 0.0974(9) Uani 1 1 d . . . . .
H00U H 0.2952 1.1026 0.3389 0.146 Uiso 1 1 calc GR . . . .
H00V H 0.2704 1.1758 0.3933 0.146 Uiso 1 1 calc GR . . . .
H00W H 0.2326 1.0830 0.3513 0.146 Uiso 1 1 calc GR . . . .
C00U C 0.62488(12) 0.6898(3) 0.42531(17) 0.1011(10) Uani 1 1 d . . . . .
H00X H 0.6313 0.7224 0.3817 0.152 Uiso 1 1 calc GR . . . .
H00Y H 0.6409 0.6175 0.4298 0.152 Uiso 1 1 calc GR . . . .
H H 0.6429 0.7333 0.4654 0.152 Uiso 1 1 calc GR . . . .
C00V C 0.56885(18) 0.7556(3) 0.59531(18) 0.1214(13) Uani 1 1 d . . . . .
H00Z H 0.5845 0.8087 0.5673 0.182 Uiso 1 1 calc GR . . . .
HA H 0.5944 0.7465 0.6407 0.182 Uiso 1 1 calc GR . . . .
HB H 0.5321 0.7801 0.6029 0.182 Uiso 1 1 calc GR . . . .


_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
F001 B00R 1.389(3) . ?
F002 B00R 1.381(3) . ?
O003 C00A 1.235(2) . ?
N004 C008 1.389(2) . ?
N004 C00B 1.338(3) . ?
N004 B00R 1.547(3) . ?
N005 C00C 1.391(3) . ?
N005 C00J 1.352(3) . ?
N005 B00R 1.533(3) . ?
N006 H006 0.8600 . ?
N006 C009 1.368(3) . ?
N006 C00I 1.342(3) . ?
C007 C008 1.395(3) . ?
C007 C00A 1.502(3) . ?
C007 C00C 1.392(3) . ?
C008 C00E 1.432(3) . ?
C009 C00A 1.425(3) . ?
C009 C00D 1.403(3) . ?
C00B C00F 1.406(3) . ?
C00B C00M 1.487(3) . ?
C00C C00H 1.421(3) . ?
C00D C00G 1.392(3) . ?
C00D C00L 1.495(3) . ?
C00E C00F 1.376(3) . ?
C00E C00Q 1.483(3) . ?
C00F C00O 1.504(3) . ?
C00G C00I 1.383(3) . ?
C00G C00N 1.507(3) . ?
C00H C00K 1.359(4) . ?
C00H C00P 1.504(4) . ?
C00I C00U 1.489(4) . ?
C00J C00K 1.385(4) . ?
C00J C00S 1.493(4) . ?
C00K H00K 0.9300 . ?
C00L H00A 0.9600 . ?
C00L H00B 0.9600 . ?
C00L H00C 0.9600 . ?
C00M H00D 0.9600 . ?
C00M H00E 0.9600 . ?
C00M H00F 0.9600 . ?
C00N H00G 0.9700 . ?
C00N H00H 0.9700 . ?
C00N C00V 1.503(4) . ?
C00O H00I 0.9700 . ?
C00O H00J 0.9700 . ?
C00O C00T 1.500(4) . ?
C00P H00L 0.9600 . ?
C00P H00M 0.9600 . ?
C00P H00N 0.9600 . ?
C00Q H00O 0.9600 . ?
C00Q H00P 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00S H00R 0.9600 . ?
C00S H00S 0.9600 . ?
C00S H00T 0.9600 . ?
C00T H00U 0.9600 . ?
C00T H00V 0.9600 . ?
C00T H00W 0.9600 . ?
C00U H00X 0.9600 . ?
C00U H00Y 0.9600 . ?
C00U H 0.9600 . ?
C00V H00Z 0.9600 . ?
C00V HA 0.9600 . ?
C00V HB 0.9600 . ?

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
C008 N004 B00R 124.91(17) . . ?
C00B N004 C008 108.06(17) . . ?
C00B N004 B00R 127.03(18) . . ?
C00C N005 B00R 125.69(17) . . ?
C00J N005 C00C 107.88(19) . . ?
C00J N005 B00R 126.4(2) . . ?
C009 N006 H006 124.9 . . ?
C00I N006 H006 124.9 . . ?
C00I N006 C009 110.30(18) . . ?
C008 C007 C00A 119.99(18) . . ?
C00C C007 C008 121.93(19) . . ?
C00C C007 C00A 118.07(18) . . ?
N004 C008 C007 120.20(17) . . ?
N004 C008 C00E 108.04(17) . . ?
C007 C008 C00E 131.76(19) . . ?
N006 C009 C00A 118.80(18) . . ?
N006 C009 C00D 106.92(18) . . ?
C00D C009 C00A 134.21(19) . . ?
O003 C00A C007 117.56(19) . . ?
O003 C00A C009 123.48(19) . . ?
C009 C00A C007 118.95(17) . . ?
N004 C00B C00F 109.82(18) . . ?
N004 C00B C00M 122.4(2) . . ?
C00F C00B C00M 127.7(2) . . ?
N005 C00C C007 119.74(18) . . ?
N005 C00C C00H 107.72(19) . . ?
C007 C00C C00H 132.5(2) . . ?
C009 C00D C00L 127.9(2) . . ?
C00G C00D C009 106.89(19) . . ?
C00G C00D C00L 125.2(2) . . ?
C008 C00E C00Q 127.3(2) . . ?
C00F C00E C008 106.22(19) . . ?
C00F C00E C00Q 126.5(2) . . ?
C00B C00F C00O 125.2(2) . . ?
C00E C00F C00B 107.85(19) . . ?
C00E C00F C00O 126.9(2) . . ?
C00D C00G C00N 128.1(2) . . ?
C00I C00G C00D 107.9(2) . . ?
C00I C00G C00N 123.9(2) . . ?
C00C C00H C00P 128.6(2) . . ?
C00K C00H C00C 106.3(2) . . ?
C00K C00H C00P 125.1(2) . . ?
N006 C00I C00G 108.0(2) . . ?
N006 C00I C00U 122.1(2) . . ?
C00G C00I C00U 129.9(2) . . ?
N005 C00J C00K 108.8(2) . . ?
N005 C00J C00S 122.4(2) . . ?
C00K C00J C00S 128.8(2) . . ?
C00H C00K C00J 109.4(2) . . ?
C00H C00K H00K 125.3 . . ?
C00J C00K H00K 125.3 . . ?
C00D C00L H00A 109.5 . . ?
C00D C00L H00B 109.5 . . ?
C00D C00L H00C 109.5 . . ?
H00A C00L H00B 109.5 . . ?
H00A C00L H00C 109.5 . . ?
H00B C00L H00C 109.5 . . ?
C00B C00M H00D 109.5 . . ?
C00B C00M H00E 109.5 . . ?
C00B C00M H00F 109.5 . . ?
H00D C00M H00E 109.5 . . ?
H00D C00M H00F 109.5 . . ?
H00E C00M H00F 109.5 . . ?
C00G C00N H00G 109.1 . . ?
C00G C00N H00H 109.1 . . ?
H00G C00N H00H 107.9 . . ?
C00V C00N C00G 112.3(2) . . ?
C00V C00N H00G 109.1 . . ?
C00V C00N H00H 109.1 . . ?
C00F C00O H00I 109.0 . . ?
C00F C00O H00J 109.0 . . ?
H00I C00O H00J 107.8 . . ?
C00T C00O C00F 112.9(2) . . ?
C00T C00O H00I 109.0 . . ?
C00T C00O H00J 109.0 . . ?
C00H C00P H00L 109.5 . . ?
C00H C00P H00M 109.5 . . ?
C00H C00P H00N 109.5 . . ?
H00L C00P H00M 109.5 . . ?
H00L C00P H00N 109.5 . . ?
H00M C00P H00N 109.5 . . ?
C00E C00Q H00O 109.5 . . ?
C00E C00Q H00P 109.5 . . ?
C00E C00Q H00Q 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 109.5 . . ?
F001 B00R N004 109.50(19) . . ?
F001 B00R N005 109.98(18) . . ?
F002 B00R F001 108.75(19) . . ?
F002 B00R N004 110.33(18) . . ?
F002 B00R N005 110.8(2) . . ?
N005 B00R N004 107.44(17) . . ?
C00J C00S H00R 109.5 . . ?
C00J C00S H00S 109.5 . . ?
C00J C00S H00T 109.5 . . ?
H00R C00S H00S 109.5 . . ?
H00R C00S H00T 109.5 . . ?
H00S C00S H00T 109.5 . . ?
C00O C00T H00U 109.5 . . ?
C00O C00T H00V 109.5 . . ?
C00O C00T H00W 109.5 . . ?
H00U C00T H00V 109.5 . . ?
H00U C00T H00W 109.5 . . ?
H00V C00T H00W 109.5 . . ?
C00I C00U H00X 109.5 . . ?
C00I C00U H00Y 109.5 . . ?
C00I C00U H 109.5 . . ?
H00X C00U H00Y 109.5 . . ?
H00X C00U H 109.5 . . ?
H00Y C00U H 109.5 . . ?
C00N C00V H00Z 109.5 . . ?
C00N C00V HA 109.5 . . ?
C00N C00V HB 109.5 . . ?
H00Z C00V HA 109.5 . . ?
H00Z C00V HB 109.5 . . ?
HA C00V HB 109.5 . . ?

_platon_squeeze_details          
;

;
_olex2_submission_special_instructions 'No special instructions were received'
