# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_LD023
_database_code_depnum_ccdc_archive 'CCDC 2279453'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin, Institut fuer Chemie und Biochemie, Anorganische Chemie
Germany
;
_audit_update_record             
;
2023-07-06 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C9 H10 B F3 N3 P'
_chemical_formula_sum            'C9 H10 B F3 N3 P'
_chemical_formula_weight         258.993
_chemical_absolute_configuration unk
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
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 '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 0.21560 '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 0.27760 '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 0.00304 '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 -11.52900 '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'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11490 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   5.80174(8)
_cell_length_b                   8.60271(12)
_cell_length_c                   11.79661(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.5596(5)
_cell_angle_gamma                90
_cell_volume                     580.601(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    168.00
_cell_measurement_theta_max      26.38
_cell_measurement_theta_min      2.94
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.8598
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1231 before and 0.0510 after correction.
The Ratio of minimum to maximum transmission is 0.9127.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_description       rod
_exptl_crystal_F_000             264.421
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 0.9947
_diffrn_reflns_Laue_measured_fraction_max 0.9953
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14658
_diffrn_reflns_point_group_measured_fraction_full 0.9943
_diffrn_reflns_point_group_measured_fraction_max 0.9950
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.94
_diffrn_ambient_temperature      168.00
_diffrn_measured_fraction_theta_full 0.9947
_diffrn_measured_fraction_theta_max 0.9953
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.995
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              14
_reflns_limit_l_min              -14
_reflns_number_gt                2354
_reflns_number_total             2376
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.5100
_refine_diff_density_min         -0.3190
_refine_diff_density_rms         0.1158
_refine_ls_abs_structure_details 
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   -0.00(2)
_refine_ls_d_res_high            0.7997
_refine_ls_d_res_low             6.9168
_refine_ls_goodness_of_fit_ref   1.1590
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0264
_refine_ls_R_factor_gt           0.0261
_refine_ls_restrained_S_all      1.1590
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0382P)²+0.0481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0590
_refine_ls_wR_factor_ref         0.0594
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
1.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
1.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
;
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
P1 P 0.40310(5) 0.51194(4) 0.74978(2) 0.01795(9) Uani 1.000000 .
F1 F 0.49064(16) 0.21973(9) 1.00838(7) 0.03022(19) Uani 1.000000 .
F2 F 0.27149(14) 0.18486(9) 0.83001(8) 0.0310(2) Uani 1.000000 .
F3 F 0.65456(14) 0.11164(9) 0.86395(7) 0.02826(18) Uani 1.000000 .
N1 N 0.63195(18) 0.63886(11) 0.77060(9) 0.0163(2) Uani 1.000000 .
N2 N 0.81526(18) 0.60069(12) 0.84581(9) 0.0179(2) Uani 1.000000 .
N3 N 0.77280(17) 0.46386(11) 0.88865(9) 0.0163(2) Uani 1.000000 .
C1 C 0.5653(2) 0.39448(14) 0.84968(10) 0.0161(2) Uani 1.000000 .
C2 C 0.6388(2) 0.79511(14) 0.71707(12) 0.0234(3) Uani 1.000000 .
H2a H 0.6078(2) 0.87629(14) 0.77210(12) 0.0281(3) Uiso 1.000000 R
H2b H 0.7957(2) 0.81398(14) 0.69728(12) 0.0281(3) Uiso 1.000000 R
C3 C 0.4572(2) 0.80330(13) 0.61029(11) 0.0185(2) Uani 1.000000 .
C4 C 0.2522(2) 0.88868(15) 0.60851(11) 0.0218(3) Uani 1.000000 .
H4 H 0.2281(2) 0.94602(15) 0.67438(11) 0.0262(3) Uiso 1.000000 R
C5 C 0.0823(2) 0.88958(15) 0.50960(13) 0.0256(3) Uani 1.000000 .
H5 H -0.0562(2) 0.94902(15) 0.50784(13) 0.0307(3) Uiso 1.000000 R
C6 C 0.1151(2) 0.80429(15) 0.41425(12) 0.0253(3) Uani 1.000000 .
H6 H -0.0027(2) 0.80339(15) 0.34790(12) 0.0303(3) Uiso 1.000000 R
C7 C 0.3201(2) 0.71964(15) 0.41486(10) 0.0225(3) Uani 1.000000 .
H7 H 0.3430(2) 0.66210(15) 0.34891(10) 0.0270(3) Uiso 1.000000 R
C8 C 0.4905(2) 0.71999(14) 0.51259(11) 0.0204(2) Uani 1.000000 .
H8 H 0.6310(2) 0.66309(14) 0.51303(11) 0.0245(3) Uiso 1.000000 R
C9 C 0.9551(2) 0.40122(17) 0.97907(12) 0.0274(3) Uani 1.000000 .
H9a H 1.0013(16) 0.2975(6) 0.9567(5) 0.0412(4) Uiso 1.000000 GR
H9b H 1.0914(9) 0.4703(8) 0.9891(8) 0.0412(4) Uiso 1.000000 GR
H9c H 0.8940(8) 0.3942(14) 1.0515(3) 0.0412(4) Uiso 1.000000 GR
B1 B 0.4938(2) 0.22128(17) 0.89056(12) 0.0202(3) Uani 1.000000 .


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
P1 N1 1.7050(10) . ?
P1 C1 1.7108(12) . ?
F1 B1 1.3931(16) . ?
F2 B1 1.4021(16) . ?
F3 B1 1.3982(17) . ?
N1 N2 1.3087(15) . ?
N1 C2 1.4884(15) . ?
N2 N3 1.3203(15) . ?
N3 C1 1.3539(15) . ?
N3 C9 1.4740(15) . ?
C1 B1 1.6405(19) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.5033(17) . ?
C3 C4 1.3954(17) . ?
C3 C8 1.3977(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3966(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.382(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.3932(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3887(18) . ?
C8 H8 0.9500 . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 N1 87.30(5) . . ?
N2 N1 P1 117.56(8) . . ?
C2 N1 P1 126.31(8) . . ?
C2 N1 N2 116.00(10) . . ?
N3 N2 N1 107.51(9) . . ?
C1 N3 N2 118.36(10) . . ?
C9 N3 N2 116.48(10) . . ?
C9 N3 C1 125.13(11) . . ?
N3 C1 P1 109.26(9) . . ?
B1 C1 P1 127.01(9) . . ?
B1 C1 N3 123.68(10) . . ?
H2a C2 N1 109.78(7) . . ?
H2b C2 N1 109.78(7) . . ?
H2b C2 H2a 108.2 . . ?
C3 C2 N1 109.48(10) . . ?
C3 C2 H2a 109.78(7) . . ?
C3 C2 H2b 109.78(7) . . ?
C4 C3 C2 120.94(12) . . ?
C8 C3 C2 119.56(11) . . ?
C8 C3 C4 119.46(12) . . ?
H4 C4 C3 120.10(8) . . ?
C5 C4 C3 119.80(12) . . ?
C5 C4 H4 120.10(8) . . ?
H5 C5 C4 119.88(8) . . ?
C6 C5 C4 120.23(12) . . ?
C6 C5 H5 119.88(7) . . ?
H6 C6 C5 119.80(7) . . ?
C7 C6 C5 120.39(12) . . ?
C7 C6 H6 119.80(8) . . ?
H7 C7 C6 120.24(8) . . ?
C8 C7 C6 119.52(12) . . ?
C8 C7 H7 120.24(8) . . ?
C7 C8 C3 120.58(12) . . ?
H8 C8 C3 119.71(7) . . ?
H8 C8 C7 119.71(8) . . ?
H9a C9 N3 109.5 . . ?
H9b C9 N3 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 N3 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
F2 B1 F1 110.04(11) . . ?
F3 B1 F1 109.71(11) . . ?
F3 B1 F2 109.05(11) . . ?
C1 B1 F1 110.35(11) . . ?
C1 B1 F2 108.02(10) . . ?
C1 B1 F3 109.64(10) . . ?

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
P1 N1 N2 N3 0.30(9) . . . . ?
P1 N1 C2 C3 -21.14(10) . . . . ?
P1 C1 N3 N2 -0.56(10) . . . . ?
P1 C1 N3 C9 177.22(8) . . . . ?
P1 C1 B1 F1 -121.10(11) . . . . ?
P1 C1 B1 F2 -0.77(10) . . . . ?
P1 C1 B1 F3 117.95(11) . . . . ?
F1 B1 C1 N3 61.77(13) . . . . ?
F2 B1 C1 N3 -177.90(9) . . . . ?
F3 B1 C1 N3 -59.19(12) . . . . ?
N1 N2 N3 C1 0.18(11) . . . . ?
N1 N2 N3 C9 -177.79(9) . . . . ?
N1 C2 C3 C4 106.35(11) . . . . ?
N1 C2 C3 C8 -71.46(12) . . . . ?
N2 N3 C1 B1 177.01(10) . . . . ?
C2 C3 C4 C5 -177.57(12) . . . . ?
C2 C3 C8 C7 176.82(11) . . . . ?
C3 C4 C5 C6 1.03(14) . . . . ?
C3 C8 C7 C6 0.54(14) . . . . ?
C4 C5 C6 C7 -1.53(16) . . . . ?
C5 C6 C7 C8 0.75(15) . . . . ?


_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_ld0172
_database_code_depnum_ccdc_archive 'CCDC 2279455'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin, Institut fuer Chemie und Biochemie, Anorganische Chemie
Germany
;
_audit_update_record             
;
2023-07-05 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2021-04-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H23 N3 P, F6 P'
_chemical_formula_sum            'C15 H23 F6 N3 P2'
_chemical_formula_weight         421.30
_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'
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'
P P 0.1023 0.0942 '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                   10.3822(4)
_cell_length_b                   8.4426(2)
_cell_length_c                   21.5901(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.4340(10)
_cell_angle_gamma                90
_cell_volume                     1883.93(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.39
_cell_measurement_theta_min      2.27
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0953 before and 0.0597 after correction.
The Ratio of minimum to maximum transmission is 0.9378.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             872
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 4.00 -5.00 0.0920
0.00 -4.00 5.00 0.1080
4.00 -3.00 -5.00 0.0380
3.00 -1.00 -5.00 0.0230
-3.00 1.00 5.00 0.0150
-1.00 -3.00 1.00 0.0920
3.00 1.00 8.00 0.0760
-1.00 0.00 -3.00 0.0680

_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            44368
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.527
_diffrn_reflns_theta_min         2.104
_diffrn_ambient_temperature      99.95
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                4827
_reflns_number_total             5744
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         5744
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0597
_refine_ls_restrained_S_all      1.049
_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)+(0.0850P)²+2.7682P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C4(H4), C1(H1)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C9(H9A,H9B,H9C)
;
_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
P1 P 0.72845(6) 0.65173(7) 0.47662(3) 0.02214(14) Uani 1 1 d . . . . .
P2 P 0.59984(6) 0.90784(7) 0.61967(3) 0.02271(14) Uani 1 1 d . . . . .
F5 F 0.70241(16) 0.8011(2) 0.58804(8) 0.0402(4) Uani 1 1 d . . . . .
F6 F 0.49484(16) 1.0132(2) 0.65074(9) 0.0442(4) Uani 1 1 d . . . . .
F3 F 0.48773(17) 0.7938(2) 0.59023(9) 0.0466(5) Uani 1 1 d . . . . .
F2 F 0.6188(2) 0.7994(3) 0.68057(8) 0.0500(5) Uani 1 1 d . . . . .
N1 N 0.72656(16) 0.5538(2) 0.40727(7) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.61629(16) 0.5397(2) 0.37224(8) 0.0173(3) Uani 1 1 d . . . . .
F4 F 0.71448(18) 1.0173(3) 0.65060(10) 0.0514(5) Uani 1 1 d . . . . .
N3 N 0.52721(17) 0.6096(2) 0.40195(8) 0.0197(3) Uani 1 1 d . . . . .
F1 F 0.5858(2) 1.0182(3) 0.56035(9) 0.0536(5) Uani 1 1 d . . . . .
C3 C 0.90098(19) 0.5762(2) 0.33935(9) 0.0164(4) Uani 1 1 d . . . . .
C2 C 0.84142(18) 0.4873(2) 0.38339(8) 0.0147(3) Uani 1 1 d . . . . .
C7 C 0.88633(19) 0.3405(2) 0.40728(9) 0.0166(3) Uani 1 1 d . . . . .
C8 C 0.8511(2) 0.7365(2) 0.31584(9) 0.0191(4) Uani 1 1 d . . . . .
H8 H 0.792378 0.778636 0.346083 0.023 Uiso 1 1 calc R U . . .
C6 C 0.9983(2) 0.2824(3) 0.38431(10) 0.0197(4) Uani 1 1 d . . . . .
H6 H 1.033686 0.184620 0.399615 0.024 Uiso 1 1 calc R U . . .
C5 C 1.0590(2) 0.3646(3) 0.33947(10) 0.0210(4) Uani 1 1 d . . . . .
H5 H 1.134349 0.321680 0.324140 0.025 Uiso 1 1 calc R U . . .
C4 C 1.0106(2) 0.5086(3) 0.31690(9) 0.0205(4) Uani 1 1 d . . . . .
H4 H 1.052467 0.562293 0.285723 0.025 Uiso 1 1 calc R U . . .
C11 C 0.81971(19) 0.2496(2) 0.45583(9) 0.0186(4) Uani 1 1 d . . . . .
H11 H 0.731492 0.295964 0.457554 0.022 Uiso 1 1 calc R U . . .
C1 C 0.5663(2) 0.6763(3) 0.45776(10) 0.0230(4) Uani 1 1 d . . . . .
H1 H 0.510477 0.729884 0.483167 0.028 Uiso 1 1 calc R U . . .
C10 C 0.9618(2) 0.8546(3) 0.31234(11) 0.0263(4) Uani 1 1 d . . . . .
H10A H 1.015364 0.856449 0.352237 0.039 Uiso 1 1 calc R U . . .
H10B H 0.926197 0.960489 0.303265 0.039 Uiso 1 1 calc R U . . .
H10C H 1.014889 0.822624 0.279282 0.039 Uiso 1 1 calc R U . . .
C14 C 0.3914(2) 0.6054(3) 0.37292(12) 0.0276(5) Uani 1 1 d . . . . .
H14A H 0.340732 0.688637 0.391959 0.033 Uiso 1 1 calc R U . . .
H14B H 0.352530 0.501667 0.381630 0.033 Uiso 1 1 calc R U . . .
C12 C 0.8034(2) 0.0745(3) 0.43924(12) 0.0280(5) Uani 1 1 d . . . . .
H12A H 0.757214 0.064315 0.397699 0.042 Uiso 1 1 calc R U . . .
H12B H 0.753857 0.022005 0.469781 0.042 Uiso 1 1 calc R U . . .
H12C H 0.888780 0.024734 0.439577 0.042 Uiso 1 1 calc R U . . .
C13 C 0.8938(2) 0.2690(3) 0.52040(10) 0.0273(5) Uani 1 1 d . . . . .
H13A H 0.981555 0.226628 0.519688 0.041 Uiso 1 1 calc R U . . .
H13B H 0.848738 0.211093 0.551253 0.041 Uiso 1 1 calc R U . . .
H13C H 0.898446 0.381530 0.531468 0.041 Uiso 1 1 calc R U . . .
C15 C 0.3828(2) 0.6309(4) 0.30347(12) 0.0321(5) Uani 1 1 d . . . . .
H15A H 0.428711 0.545335 0.284122 0.048 Uiso 1 1 calc R U . . .
H15B H 0.422448 0.732735 0.294571 0.048 Uiso 1 1 calc R U . . .
H15C H 0.291826 0.631080 0.286605 0.048 Uiso 1 1 calc R U . . .
C9 C 0.7726(3) 0.7201(3) 0.25273(12) 0.0314(5) Uani 1 1 d . . . . .
H9A H 0.828138 0.678369 0.222273 0.047 Uiso 1 1 calc R U . . .
H9B H 0.739066 0.824047 0.238976 0.047 Uiso 1 1 calc R U . . .
H9C H 0.700232 0.647244 0.256410 0.047 Uiso 1 1 calc R U . . .


_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
P1 N1 1.7090(17) . ?
P1 C1 1.706(2) . ?
P2 F5 1.5971(16) . ?
P2 F6 1.6026(17) . ?
P2 F3 1.5956(18) . ?
P2 F2 1.5992(19) . ?
P2 F4 1.6018(19) . ?
P2 F1 1.5791(19) . ?
N1 N2 1.316(2) . ?
N1 C2 1.456(2) . ?
N2 N3 1.314(2) . ?
N3 C1 1.357(3) . ?
N3 C14 1.488(3) . ?
C3 C2 1.401(3) . ?
C3 C8 1.519(3) . ?
C3 C4 1.400(3) . ?
C2 C7 1.405(3) . ?
C7 C6 1.395(3) . ?
C7 C11 1.518(3) . ?
C8 H8 1.0000 . ?
C8 C10 1.529(3) . ?
C8 C9 1.526(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.527(3) . ?
C11 C13 1.536(3) . ?
C1 H1 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.509(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 N1 85.44(9) . . ?
F5 P2 F6 178.97(11) . . ?
F5 P2 F2 89.61(10) . . ?
F5 P2 F4 90.26(10) . . ?
F3 P2 F5 88.84(10) . . ?
F3 P2 F6 90.14(10) . . ?
F3 P2 F2 90.58(12) . . ?
F3 P2 F4 178.02(12) . . ?
F2 P2 F6 90.54(11) . . ?
F2 P2 F4 87.64(12) . . ?
F4 P2 F6 90.76(10) . . ?
F1 P2 F5 90.02(10) . . ?
F1 P2 F6 89.87(11) . . ?
F1 P2 F3 91.43(12) . . ?
F1 P2 F2 177.95(13) . . ?
F1 P2 F4 90.34(13) . . ?
N2 N1 P1 118.96(13) . . ?
N2 N1 C2 117.31(16) . . ?
C2 N1 P1 123.71(13) . . ?
N3 N2 N1 107.04(16) . . ?
N2 N3 C1 117.02(18) . . ?
N2 N3 C14 117.79(18) . . ?
C1 N3 C14 125.16(18) . . ?
C2 C3 C8 123.10(18) . . ?
C4 C3 C2 116.25(18) . . ?
C4 C3 C8 120.65(18) . . ?
C3 C2 N1 117.57(17) . . ?
C3 C2 C7 124.72(18) . . ?
C7 C2 N1 117.69(16) . . ?
C2 C7 C11 122.86(18) . . ?
C6 C7 C2 116.01(18) . . ?
C6 C7 C11 121.12(18) . . ?
C3 C8 H8 107.9 . . ?
C3 C8 C10 111.31(18) . . ?
C3 C8 C9 110.70(18) . . ?
C10 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C9 C8 C10 110.83(18) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.31(19) . . ?
C5 C6 H6 119.3 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.66(19) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 120.99(19) . . ?
C5 C4 H4 119.5 . . ?
C7 C11 H11 107.8 . . ?
C7 C11 C12 112.03(18) . . ?
C7 C11 C13 110.56(17) . . ?
C12 C11 H11 107.8 . . ?
C12 C11 C13 110.55(19) . . ?
C13 C11 H11 107.8 . . ?
P1 C1 H1 124.2 . . ?
N3 C1 P1 111.54(15) . . ?
N3 C1 H1 124.2 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
N3 C14 C15 112.30(18) . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 N1 N2 N3 -0.4(2) . . . . ?
P1 N1 C2 C3 -98.52(19) . . . . ?
P1 N1 C2 C7 80.0(2) . . . . ?
N1 P1 C1 N3 -0.09(16) . . . . ?
N1 N2 N3 C1 0.3(2) . . . . ?
N1 N2 N3 C14 -177.90(18) . . . . ?
N1 C2 C7 C6 -178.60(17) . . . . ?
N1 C2 C7 C11 0.6(3) . . . . ?
N2 N1 C2 C3 79.9(2) . . . . ?
N2 N1 C2 C7 -101.6(2) . . . . ?
N2 N3 C1 P1 -0.1(2) . . . . ?
N2 N3 C14 C15 -40.7(3) . . . . ?
C3 C2 C7 C6 -0.2(3) . . . . ?
C3 C2 C7 C11 178.95(18) . . . . ?
C2 N1 N2 N3 -178.90(16) . . . . ?
C2 C3 C8 C10 136.6(2) . . . . ?
C2 C3 C8 C9 -99.7(2) . . . . ?
C2 C3 C4 C5 -2.5(3) . . . . ?
C2 C7 C6 C5 -1.3(3) . . . . ?
C2 C7 C11 C12 133.8(2) . . . . ?
C2 C7 C11 C13 -102.4(2) . . . . ?
C7 C6 C5 C4 0.9(3) . . . . ?
C8 C3 C2 N1 -0.1(3) . . . . ?
C8 C3 C2 C7 -178.46(18) . . . . ?
C8 C3 C4 C5 178.06(19) . . . . ?
C6 C7 C11 C12 -47.1(3) . . . . ?
C6 C7 C11 C13 76.7(2) . . . . ?
C6 C5 C4 C3 1.1(3) . . . . ?
C4 C3 C2 N1 -179.51(17) . . . . ?
C4 C3 C2 C7 2.1(3) . . . . ?
C4 C3 C8 C10 -44.0(3) . . . . ?
C4 C3 C8 C9 79.7(2) . . . . ?
C11 C7 C6 C5 179.46(19) . . . . ?
C1 P1 N1 N2 0.30(16) . . . . ?
C1 P1 N1 C2 178.69(17) . . . . ?
C1 N3 C14 C15 141.2(2) . . . . ?
C14 N3 C1 P1 177.96(17) . . . . ?

_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_0180ld
_database_code_depnum_ccdc_archive 'CCDC 2279454'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin, Institut fuer Chemie und Biochemie, Anorganische Chemie
Germany
;
_audit_update_record             
;
2023-07-06 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 B F3 N3 P'
_chemical_formula_sum            'C14 H20 B F3 N3 P'
_chemical_formula_weight         329.11
_chemical_absolute_configuration ?
_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'
P P 0.1023 0.0942 '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      orthorhombic
_space_group_IT_number           32
_space_group_name_H-M_alt        'P b a 2'
_space_group_name_Hall           'P 2 -2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z'

_cell_length_a                   11.2355(2)
_cell_length_b                   30.5407(5)
_cell_length_c                   9.5592(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3280.14(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9849
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.71
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_correction_T_min  0.9045
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1532 before and 0.0610 after correction.
The Ratio of minimum to maximum transmission is 0.9320.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            41596
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.713
_diffrn_reflns_theta_min         1.931
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_full    0.934
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                5840
_reflns_number_total             6034
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 2493 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       0.0017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     408
_refine_ls_number_reflns         6034
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.047
_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)+(0.0368P)²+0.8430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0688
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C8A(H8A), C11A(H11A), C8B(H8B), C11B(H11B)
1.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C6A(H6A), C4B(H4B), C5B(H5B), C6B(H6B)
1.c Idealised Me refined as rotating group:
 C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,H10C), C12A(H12A,H12B,H12C), C13A(H13A,
 H13B,H13C), C14A(H14A,H14B,H14C), C9B(H9BA,H9BB,H9BC), C10B(H10D,H10E,H10F),
 C12B(H12D,H12E,H12F), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F)
;
_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
P1A P 0.23930(5) 0.81052(2) 0.83039(7) 0.01877(14) Uani 1 1 d . . . . .
F1A F 0.45276(12) 0.71242(4) 0.86294(18) 0.0331(4) Uani 1 1 d . . . . .
F2A F 0.34093(15) 0.69906(4) 0.67015(17) 0.0350(4) Uani 1 1 d . . . . .
F3A F 0.25051(13) 0.71231(5) 0.87775(19) 0.0361(4) Uani 1 1 d . . . . .
N1A N 0.31268(15) 0.85141(5) 0.7453(2) 0.0147(4) Uani 1 1 d . . . . .
N2A N 0.40745(15) 0.84098(5) 0.6715(2) 0.0157(4) Uani 1 1 d . . . . .
N3A N 0.42136(15) 0.79805(5) 0.6834(2) 0.0162(4) Uani 1 1 d . . . . .
C1A C 0.34251(18) 0.77533(7) 0.7625(2) 0.0160(4) Uani 1 1 d . . . . .
C2A C 0.28187(18) 0.89777(6) 0.7552(2) 0.0156(4) Uani 1 1 d . . . . .
C3A C 0.19761(18) 0.91468(7) 0.6622(2) 0.0174(4) Uani 1 1 d . . . . .
C4A C 0.1661(2) 0.95823(7) 0.6804(3) 0.0222(5) Uani 1 1 d . . . . .
H4A H 0.110503 0.971220 0.618025 0.027 Uiso 1 1 calc R U . . .
C5A C 0.2140(2) 0.98320(7) 0.7877(3) 0.0251(5) Uani 1 1 d . . . . .
H5A H 0.189789 1.012775 0.799371 0.030 Uiso 1 1 calc R U . . .
C6A C 0.2969(2) 0.96519(7) 0.8777(3) 0.0224(5) Uani 1 1 d . . . . .
H6A H 0.328747 0.982557 0.951145 0.027 Uiso 1 1 calc R U . . .
C7A C 0.33435(18) 0.92200(6) 0.8625(2) 0.0174(5) Uani 1 1 d . . . . .
C8A C 0.14882(19) 0.88785(7) 0.5415(2) 0.0190(5) Uani 1 1 d . . . . .
H8A H 0.147618 0.856441 0.570938 0.023 Uiso 1 1 calc R U . . .
C9A C 0.2316(2) 0.89191(7) 0.4155(3) 0.0221(5) Uani 1 1 d . . . . .
H9AA H 0.199446 0.874828 0.337405 0.033 Uiso 1 1 calc R U . . .
H9AB H 0.310621 0.880761 0.440327 0.033 Uiso 1 1 calc R U . . .
H9AC H 0.237868 0.922732 0.388039 0.033 Uiso 1 1 calc R U . . .
C10A C 0.0224(2) 0.90079(9) 0.5005(3) 0.0326(6) Uani 1 1 d . . . . .
H10A H 0.022795 0.930439 0.461326 0.049 Uiso 1 1 calc R U . . .
H10B H -0.028800 0.900058 0.583505 0.049 Uiso 1 1 calc R U . . .
H10C H -0.007992 0.880194 0.430530 0.049 Uiso 1 1 calc R U . . .
C11A C 0.42782(19) 0.90335(7) 0.9614(2) 0.0186(5) Uani 1 1 d . . . . .
H11A H 0.450023 0.873480 0.927403 0.022 Uiso 1 1 calc R U . . .
C12A C 0.5400(2) 0.93176(8) 0.9614(3) 0.0286(6) Uani 1 1 d . . . . .
H12A H 0.565559 0.936956 0.864753 0.043 Uiso 1 1 calc R U . . .
H12B H 0.603474 0.916699 1.012580 0.043 Uiso 1 1 calc R U . . .
H12C H 0.522750 0.959833 1.006715 0.043 Uiso 1 1 calc R U . . .
C13A C 0.3784(2) 0.89899(8) 1.1086(3) 0.0279(5) Uani 1 1 d . . . . .
H13A H 0.307815 0.880136 1.106990 0.042 Uiso 1 1 calc R U . . .
H13B H 0.356505 0.927993 1.144067 0.042 Uiso 1 1 calc R U . . .
H13C H 0.438944 0.886015 1.169600 0.042 Uiso 1 1 calc R U . . .
C14A C 0.5235(2) 0.77900(7) 0.6082(3) 0.0235(5) Uani 1 1 d . . . . .
H14A H 0.514826 0.747093 0.604398 0.035 Uiso 1 1 calc R U . . .
H14B H 0.597317 0.786458 0.657398 0.035 Uiso 1 1 calc R U . . .
H14C H 0.526313 0.790776 0.512927 0.035 Uiso 1 1 calc R U . . .
B1A B 0.3481(2) 0.72216(8) 0.7936(3) 0.0201(5) Uani 1 1 d . . . . .
P1B P 0.31441(5) 0.68750(2) 0.34069(7) 0.01704(13) Uani 1 1 d . . . . .
F1B F 0.11589(13) 0.79190(4) 0.36492(18) 0.0332(4) Uani 1 1 d . . . . .
F2B F 0.24073(12) 0.80064(4) 0.18039(16) 0.0263(3) Uani 1 1 d . . . . .
F3B F 0.31681(14) 0.78565(4) 0.39542(18) 0.0362(4) Uani 1 1 d . . . . .
N1B N 0.23623(15) 0.64897(5) 0.25015(19) 0.0137(4) Uani 1 1 d . . . . .
N2B N 0.14496(15) 0.66224(5) 0.1743(2) 0.0163(4) Uani 1 1 d . . . . .
N3B N 0.13745(15) 0.70515(5) 0.1900(2) 0.0164(4) Uani 1 1 d . . . . .
C1B C 0.21773(19) 0.72536(7) 0.2736(2) 0.0166(4) Uani 1 1 d . . . . .
C2B C 0.26407(18) 0.60234(6) 0.2444(2) 0.0142(4) Uani 1 1 d . . . . .
C3B C 0.34478(18) 0.58848(7) 0.1422(2) 0.0149(4) Uani 1 1 d . . . . .
C4B C 0.3733(2) 0.54410(7) 0.1412(3) 0.0194(5) Uani 1 1 d . . . . .
H4B H 0.427260 0.533214 0.073059 0.023 Uiso 1 1 calc R U . . .
C5B C 0.3241(2) 0.51558(7) 0.2381(3) 0.0222(5) Uani 1 1 d . . . . .
H5B H 0.345942 0.485532 0.236726 0.027 Uiso 1 1 calc R U . . .
C6B C 0.24350(18) 0.53046(6) 0.3367(3) 0.0208(5) Uani 1 1 d . . . . .
H6B H 0.209739 0.510359 0.401308 0.025 Uiso 1 1 calc R U . . .
C7B C 0.21104(17) 0.57454(6) 0.3426(3) 0.0160(4) Uani 1 1 d . . . . .
C8B C 0.40273(19) 0.61979(7) 0.0392(2) 0.0169(4) Uani 1 1 d . . . . .
H8B H 0.357799 0.648036 0.042729 0.020 Uiso 1 1 calc R U . . .
C9B C 0.5300(2) 0.62907(9) 0.0839(3) 0.0339(6) Uani 1 1 d . . . . .
H9BA H 0.576695 0.602021 0.078792 0.051 Uiso 1 1 calc R U . . .
H9BB H 0.530453 0.640109 0.180110 0.051 Uiso 1 1 calc R U . . .
H9BC H 0.564840 0.651059 0.021460 0.051 Uiso 1 1 calc R U . . .
C10B C 0.3982(2) 0.60307(8) -0.1101(3) 0.0286(5) Uani 1 1 d . . . . .
H10D H 0.427529 0.625825 -0.173647 0.043 Uiso 1 1 calc R U . . .
H10E H 0.315905 0.595671 -0.134501 0.043 Uiso 1 1 calc R U . . .
H10F H 0.448226 0.576925 -0.118629 0.043 Uiso 1 1 calc R U . . .
C11B C 0.12548(19) 0.59136(7) 0.4540(2) 0.0175(5) Uani 1 1 d . . . . .
H11B H 0.086178 0.618370 0.417079 0.021 Uiso 1 1 calc R U . . .
C12B C 0.0282(2) 0.55802(7) 0.4888(3) 0.0232(5) Uani 1 1 d . . . . .
H12D H -0.011651 0.548837 0.402486 0.035 Uiso 1 1 calc R U . . .
H12E H -0.030038 0.571414 0.552010 0.035 Uiso 1 1 calc R U . . .
H12F H 0.064024 0.532457 0.534308 0.035 Uiso 1 1 calc R U . . .
C13B C 0.1930(2) 0.60364(8) 0.5872(3) 0.0228(5) Uani 1 1 d . . . . .
H13D H 0.252654 0.626044 0.565447 0.034 Uiso 1 1 calc R U . . .
H13E H 0.232702 0.577623 0.624984 0.034 Uiso 1 1 calc R U . . .
H13F H 0.136980 0.615135 0.656702 0.034 Uiso 1 1 calc R U . . .
C14B C 0.0410(2) 0.72705(7) 0.1114(3) 0.0247(5) Uani 1 1 d . . . . .
H14D H 0.059988 0.726848 0.011315 0.037 Uiso 1 1 calc R U . . .
H14E H 0.033118 0.757369 0.143684 0.037 Uiso 1 1 calc R U . . .
H14F H -0.034080 0.711462 0.127015 0.037 Uiso 1 1 calc R U . . .
B1B B 0.2222(2) 0.77842(8) 0.3045(3) 0.0207(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1A N1A 1.7031(18) . ?
P1A C1A 1.709(2) . ?
F1A B1A 1.382(3) . ?
F2A B1A 1.377(3) . ?
F3A B1A 1.393(3) . ?
N1A N2A 1.317(2) . ?
N1A C2A 1.461(3) . ?
N2A N3A 1.325(2) . ?
N3A C1A 1.356(3) . ?
N3A C14A 1.474(3) . ?
C1A B1A 1.652(3) . ?
C2A C3A 1.398(3) . ?
C2A C7A 1.396(3) . ?
C3A C4A 1.387(3) . ?
C3A C8A 1.518(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.387(3) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.382(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.392(3) . ?
C7A C11A 1.523(3) . ?
C8A H8A 1.0000 . ?
C8A C9A 1.526(3) . ?
C8A C10A 1.525(3) . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11A H11A 1.0000 . ?
C11A C12A 1.530(3) . ?
C11A C13A 1.519(3) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
P1B N1B 1.7044(18) . ?
P1B C1B 1.711(2) . ?
F1B B1B 1.389(3) . ?
F2B B1B 1.383(3) . ?
F3B B1B 1.391(3) . ?
N1B N2B 1.320(2) . ?
N1B C2B 1.459(2) . ?
N2B N3B 1.322(2) . ?
N3B C1B 1.354(3) . ?
N3B C14B 1.479(3) . ?
C1B B1B 1.648(3) . ?
C2B C3B 1.398(3) . ?
C2B C7B 1.399(3) . ?
C3B C4B 1.393(3) . ?
C3B C8B 1.519(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(3) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.384(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.396(3) . ?
C7B C11B 1.524(3) . ?
C8B H8B 1.0000 . ?
C8B C9B 1.518(3) . ?
C8B C10B 1.517(3) . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11B 1.0000 . ?
C11B C12B 1.530(3) . ?
C11B C13B 1.530(3) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A P1A C1A 87.20(10) . . ?
N2A N1A P1A 118.04(13) . . ?
N2A N1A C2A 117.46(16) . . ?
C2A N1A P1A 124.40(14) . . ?
N1A N2A N3A 106.77(16) . . ?
N2A N3A C1A 118.52(17) . . ?
N2A N3A C14A 116.13(17) . . ?
C1A N3A C14A 125.35(17) . . ?
N3A C1A P1A 109.47(15) . . ?
N3A C1A B1A 125.35(19) . . ?
B1A C1A P1A 125.14(16) . . ?
C3A C2A N1A 118.51(18) . . ?
C7A C2A N1A 117.49(19) . . ?
C7A C2A C3A 123.91(19) . . ?
C2A C3A C8A 121.94(19) . . ?
C4A C3A C2A 116.6(2) . . ?
C4A C3A C8A 121.4(2) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A C3A 121.4(2) . . ?
C5A C4A H4A 119.3 . . ?
C4A C5A H5A 119.9 . . ?
C6A C5A C4A 120.2(2) . . ?
C6A C5A H5A 119.9 . . ?
C5A C6A H6A 119.5 . . ?
C5A C6A C7A 121.1(2) . . ?
C7A C6A H6A 119.5 . . ?
C2A C7A C11A 123.30(18) . . ?
C6A C7A C2A 116.8(2) . . ?
C6A C7A C11A 119.9(2) . . ?
C3A C8A H8A 108.0 . . ?
C3A C8A C9A 109.63(18) . . ?
C3A C8A C10A 113.0(2) . . ?
C9A C8A H8A 108.0 . . ?
C10A C8A H8A 108.0 . . ?
C10A C8A C9A 110.14(19) . . ?
C8A C9A H9AA 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
C8A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C8A C10A H10A 109.5 . . ?
C8A C10A H10B 109.5 . . ?
C8A C10A H10C 109.5 . . ?
H10A C10A H10B 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C7A C11A H11A 108.2 . . ?
C7A C11A C12A 110.85(18) . . ?
C12A C11A H11A 108.2 . . ?
C13A C11A C7A 110.82(19) . . ?
C13A C11A H11A 108.2 . . ?
C13A C11A C12A 110.6(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
N3A C14A H14A 109.5 . . ?
N3A C14A H14B 109.5 . . ?
N3A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
F1A B1A F3A 110.2(2) . . ?
F1A B1A C1A 109.27(18) . . ?
F2A B1A F1A 110.5(2) . . ?
F2A B1A F3A 109.8(2) . . ?
F2A B1A C1A 110.32(19) . . ?
F3A B1A C1A 106.62(18) . . ?
N1B P1B C1B 87.09(10) . . ?
N2B N1B P1B 117.88(13) . . ?
N2B N1B C2B 116.45(16) . . ?
C2B N1B P1B 125.62(14) . . ?
N1B N2B N3B 106.94(17) . . ?
N2B N3B C1B 118.47(17) . . ?
N2B N3B C14B 115.95(18) . . ?
C1B N3B C14B 125.58(18) . . ?
N3B C1B P1B 109.62(15) . . ?
N3B C1B B1B 125.05(19) . . ?
B1B C1B P1B 125.32(17) . . ?
C3B C2B N1B 117.45(18) . . ?
C3B C2B C7B 124.13(18) . . ?
C7B C2B N1B 118.41(18) . . ?
C2B C3B C8B 122.68(18) . . ?
C4B C3B C2B 116.67(19) . . ?
C4B C3B C8B 120.63(19) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B C3B 121.0(2) . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B H5B 119.7 . . ?
C6B C5B C4B 120.6(2) . . ?
C6B C5B H5B 119.7 . . ?
C5B C6B H6B 119.5 . . ?
C5B C6B C7B 121.0(2) . . ?
C7B C6B H6B 119.5 . . ?
C2B C7B C11B 122.20(17) . . ?
C6B C7B C2B 116.5(2) . . ?
C6B C7B C11B 121.2(2) . . ?
C3B C8B H8B 107.8 . . ?
C9B C8B C3B 109.80(19) . . ?
C9B C8B H8B 107.8 . . ?
C10B C8B C3B 112.55(18) . . ?
C10B C8B H8B 107.8 . . ?
C10B C8B C9B 111.0(2) . . ?
C8B C9B H9BA 109.5 . . ?
C8B C9B H9BB 109.5 . . ?
C8B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C8B C10B H10D 109.5 . . ?
C8B C10B H10E 109.5 . . ?
C8B C10B H10F 109.5 . . ?
H10D C10B H10E 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C7B C11B H11B 108.1 . . ?
C7B C11B C12B 112.24(18) . . ?
C7B C11B C13B 110.58(18) . . ?
C12B C11B H11B 108.1 . . ?
C13B C11B H11B 108.1 . . ?
C13B C11B C12B 109.64(19) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
N3B C14B H14D 109.5 . . ?
N3B C14B H14E 109.5 . . ?
N3B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
F1B B1B F3B 110.5(2) . . ?
F1B B1B C1B 109.87(19) . . ?
F2B B1B F1B 109.92(19) . . ?
F2B B1B F3B 110.1(2) . . ?
F2B B1B C1B 109.49(19) . . ?
F3B B1B C1B 106.94(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
P1A N1A N2A N3A 0.3(2) . . . . ?
P1A N1A C2A C3A -88.2(2) . . . . ?
P1A N1A C2A C7A 88.6(2) . . . . ?
P1A C1A B1A F1A -116.1(2) . . . . ?
P1A C1A B1A F2A 122.1(2) . . . . ?
P1A C1A B1A F3A 3.0(3) . . . . ?
N1A P1A C1A N3A 0.18(16) . . . . ?
N1A P1A C1A B1A 178.00(19) . . . . ?
N1A N2A N3A C1A -0.1(3) . . . . ?
N1A N2A N3A C14A -179.96(19) . . . . ?
N1A C2A C3A C4A 176.49(19) . . . . ?
N1A C2A C3A C8A -7.4(3) . . . . ?
N1A C2A C7A C6A -174.94(19) . . . . ?
N1A C2A C7A C11A 4.7(3) . . . . ?
N2A N1A C2A C3A 95.6(2) . . . . ?
N2A N1A C2A C7A -87.7(2) . . . . ?
N2A N3A C1A P1A -0.1(2) . . . . ?
N2A N3A C1A B1A -177.89(19) . . . . ?
N3A C1A B1A F1A 61.3(3) . . . . ?
N3A C1A B1A F2A -60.4(3) . . . . ?
N3A C1A B1A F3A -179.5(2) . . . . ?
C1A P1A N1A N2A -0.28(17) . . . . ?
C1A P1A N1A C2A -176.47(18) . . . . ?
C2A N1A N2A N3A 176.74(17) . . . . ?
C2A C3A C4A C5A -1.5(3) . . . . ?
C2A C3A C8A C9A -85.8(2) . . . . ?
C2A C3A C8A C10A 150.9(2) . . . . ?
C2A C7A C11A C12A 125.5(2) . . . . ?
C2A C7A C11A C13A -111.4(2) . . . . ?
C3A C2A C7A C6A 1.6(3) . . . . ?
C3A C2A C7A C11A -178.8(2) . . . . ?
C3A C4A C5A C6A 1.4(4) . . . . ?
C4A C3A C8A C9A 90.1(2) . . . . ?
C4A C3A C8A C10A -33.2(3) . . . . ?
C4A C5A C6A C7A 0.3(4) . . . . ?
C5A C6A C7A C2A -1.7(3) . . . . ?
C5A C6A C7A C11A 178.6(2) . . . . ?
C6A C7A C11A C12A -54.9(3) . . . . ?
C6A C7A C11A C13A 68.2(3) . . . . ?
C7A C2A C3A C4A 0.0(3) . . . . ?
C7A C2A C3A C8A 176.1(2) . . . . ?
C8A C3A C4A C5A -177.6(2) . . . . ?
C14A N3A C1A P1A 179.75(18) . . . . ?
C14A N3A C1A B1A 1.9(3) . . . . ?
P1B N1B N2B N3B -0.2(2) . . . . ?
P1B N1B C2B C3B -86.9(2) . . . . ?
P1B N1B C2B C7B 91.7(2) . . . . ?
P1B C1B B1B F1B -120.9(2) . . . . ?
P1B C1B B1B F2B 118.3(2) . . . . ?
P1B C1B B1B F3B -0.9(3) . . . . ?
N1B P1B C1B N3B -0.29(16) . . . . ?
N1B P1B C1B B1B -179.68(19) . . . . ?
N1B N2B N3B C1B -0.1(2) . . . . ?
N1B N2B N3B C14B 179.18(19) . . . . ?
N1B C2B C3B C4B 177.96(18) . . . . ?
N1B C2B C3B C8B -0.2(3) . . . . ?
N1B C2B C7B C6B -177.70(18) . . . . ?
N1B C2B C7B C11B 0.3(3) . . . . ?
N2B N1B C2B C3B 90.5(2) . . . . ?
N2B N1B C2B C7B -90.9(2) . . . . ?
N2B N3B C1B P1B 0.3(2) . . . . ?
N2B N3B C1B B1B 179.7(2) . . . . ?
N3B C1B B1B F1B 59.8(3) . . . . ?
N3B C1B B1B F2B -61.0(3) . . . . ?
N3B C1B B1B F3B 179.8(2) . . . . ?
C1B P1B N1B N2B 0.29(17) . . . . ?
C1B P1B N1B C2B 177.71(18) . . . . ?
C2B N1B N2B N3B -177.84(17) . . . . ?
C2B C3B C4B C5B -0.5(3) . . . . ?
C2B C3B C8B C9B 102.8(2) . . . . ?
C2B C3B C8B C10B -133.0(2) . . . . ?
C2B C7B C11B C12B 146.4(2) . . . . ?
C2B C7B C11B C13B -90.8(2) . . . . ?
C3B C2B C7B C6B 0.7(3) . . . . ?
C3B C2B C7B C11B 178.7(2) . . . . ?
C3B C4B C5B C6B 1.3(4) . . . . ?
C4B C3B C8B C9B -75.3(3) . . . . ?
C4B C3B C8B C10B 48.9(3) . . . . ?
C4B C5B C6B C7B -1.0(4) . . . . ?
C5B C6B C7B C2B 0.0(3) . . . . ?
C5B C6B C7B C11B -178.0(2) . . . . ?
C6B C7B C11B C12B -35.7(3) . . . . ?
C6B C7B C11B C13B 87.0(2) . . . . ?
C7B C2B C3B C4B -0.5(3) . . . . ?
C7B C2B C3B C8B -178.6(2) . . . . ?
C8B C3B C4B C5B 177.6(2) . . . . ?
C14B N3B C1B P1B -178.89(18) . . . . ?
C14B N3B C1B B1B 0.5(3) . . . . ?

_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_LB1050
_database_code_depnum_ccdc_archive 'CCDC 2279457'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin, Institut fuer Chemie und Biochemie, Anorganische Chemie
Germany
;
_audit_update_record             
;
2023-07-06 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
loop_
_audit_author_email
?
?
?
?

_audit_contact_author            
;
      Prof. Dr.Christian Müller
      Freie Universität Berlin
      Institut für Chemie und Biochemie
      Anorganische Chemie      
      Fabeckstr. 34-36
      14195 Berlin
      Germany
;
_audit_contact_letter            
;

;
_chemical_formula_moiety         'C9 H11 N3 P, B F4'
_chemical_formula_sum            'C9 H11 B F4 N3 P'
_chemical_formula_weight         278.999
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
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 '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 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 '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 0.07536 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 '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 0.00304 '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 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 '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'
P 0.30359 0.43700 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11490 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.71411(7)
_cell_length_b                   8.96879(6)
_cell_length_c                   13.55016(9)
_cell_angle_alpha                90
_cell_angle_beta                 111.9100(2)
_cell_angle_gamma                90
_cell_volume                     1208.023(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9842
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.16
_cell_measurement_theta_min      3.52
_exptl_absorpt_coefficient_mu    2.400
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1569 before and 0.1064 after correction.
The Ratio of minimum to maximum transmission is 0.6156.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.534
_exptl_crystal_description       rod
_exptl_crystal_F_000             571.568
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.05
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.9835
_diffrn_reflns_Laue_measured_fraction_max 0.9824
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18430
_diffrn_reflns_point_group_measured_fraction_full 0.9835
_diffrn_reflns_point_group_measured_fraction_max 0.9824
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         68.28
_diffrn_reflns_theta_min         4.45
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9835
_diffrn_measured_fraction_theta_max 0.9824
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -12
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2081
_reflns_number_total             2174
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2943
_refine_diff_density_min         -0.3051
_refine_diff_density_rms         0.0535
_refine_ls_d_res_high            0.8298
_refine_ls_d_res_low             9.9402
_refine_ls_goodness_of_fit_ref   1.0617
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.0617
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0343P)²+0.7898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0779
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
1.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
1.c Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c)
;
_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
P1 P 0.56155(4) 0.67251(4) 0.30872(3) 0.02209(13) Uani 1.000000 .
F1 F 0.33656(12) 0.65820(13) -0.08792(8) 0.0428(3) Uani 1.000000 .
B1 B 0.33453(18) 0.68584(19) 0.01213(13) 0.0214(4) Uani 1.000000 .
N1 N 0.69214(12) 0.67720(13) 0.42894(9) 0.0178(3) Uani 1.000000 .
C1 C 0.65333(14) 0.54110(16) 0.27454(11) 0.0195(3) Uani 1.000000 .
H1 H 0.62492(14) 0.49302(16) 0.20727(11) 0.0234(4) Uiso 1.000000 R
F2 F 0.36683(12) 0.83265(11) 0.03998(9) 0.0408(3) Uani 1.000000 .
N2 N 0.79626(12) 0.59080(13) 0.44306(9) 0.0175(3) Uani 1.000000 .
C2 C 0.70301(16) 0.78300(17) 0.51616(11) 0.0220(3) Uani 1.000000 .
H2a H 0.75478(16) 0.87160(17) 0.51005(11) 0.0265(4) Uiso 1.000000 R
H2b H 0.61174(16) 0.81680(17) 0.50804(11) 0.0265(4) Uiso 1.000000 R
N3 N 0.77063(12) 0.51426(13) 0.35465(9) 0.0168(3) Uani 1.000000 .
F3 F 0.42739(10) 0.59410(11) 0.08630(8) 0.0352(3) Uani 1.000000 .
C3 C 0.77047(15) 0.71527(16) 0.62478(11) 0.0195(3) Uani 1.000000 .
F4 F 0.20732(10) 0.65244(12) 0.01124(8) 0.0382(3) Uani 1.000000 .
C4 C 0.71685(17) 0.59139(18) 0.65596(12) 0.0255(3) Uani 1.000000 .
H4 H 0.63851(17) 0.54473(18) 0.60717(12) 0.0306(4) Uiso 1.000000 R
C5 C 0.77760(18) 0.5355(2) 0.75844(13) 0.0312(4) Uani 1.000000 .
H5 H 0.74020(18) 0.4512(2) 0.77980(13) 0.0375(5) Uiso 1.000000 R
C6 C 0.89293(17) 0.6025(2) 0.82991(12) 0.0311(4) Uani 1.000000 .
H6 H 0.93408(17) 0.5643(2) 0.90005(12) 0.0373(5) Uiso 1.000000 R
C7 C 0.94753(16) 0.7247(2) 0.79871(13) 0.0302(4) Uani 1.000000 .
H7 H 1.02681(16) 0.7701(2) 0.84724(13) 0.0362(5) Uiso 1.000000 R
C8 C 0.88664(15) 0.78132(18) 0.69642(12) 0.0245(3) Uani 1.000000 .
H8 H 0.92439(15) 0.86548(18) 0.67522(12) 0.0294(4) Uiso 1.000000 R
C9 C 0.87209(16) 0.40580(17) 0.35205(12) 0.0233(3) Uani 1.000000 .
H9a H 0.9613(2) 0.4521(4) 0.3802(9) 0.0350(5) Uiso 1.000000 GR
H9b H 0.8707(8) 0.3191(6) 0.3957(7) 0.0350(5) Uiso 1.000000 GR
H9c H 0.8519(7) 0.3738(10) 0.27854(16) 0.0350(5) Uiso 1.000000 GR


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
P1 N1 1.7066(12) . ?
P1 C1 1.7060(15) . ?
F1 B1 1.3863(19) . ?
B1 F2 1.378(2) . ?
B1 F3 1.3895(19) . ?
B1 F4 1.391(2) . ?
N1 N2 1.3123(17) . ?
N1 C2 1.4858(18) . ?
C1 H1 0.9500 . ?
C1 N3 1.3407(18) . ?
N2 N3 1.3177(16) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.505(2) . ?
N3 C9 1.4689(19) . ?
C3 C4 1.387(2) . ?
C3 C8 1.393(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.389(2) . ?
C8 H8 0.9500 . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 N1 85.75(6) . . ?
F2 B1 F1 110.16(14) . . ?
F3 B1 F1 109.46(13) . . ?
F3 B1 F2 109.20(13) . . ?
F4 B1 F1 109.02(13) . . ?
F4 B1 F2 110.69(13) . . ?
F4 B1 F3 108.27(13) . . ?
N2 N1 P1 118.30(9) . . ?
C2 N1 P1 124.61(10) . . ?
C2 N1 N2 116.81(12) . . ?
H1 C1 P1 124.28(5) . . ?
N3 C1 P1 111.43(10) . . ?
N3 C1 H1 124.28(8) . . ?
N3 N2 N1 107.32(11) . . ?
H2a C2 N1 109.04(8) . . ?
H2b C2 N1 109.04(8) . . ?
H2b C2 H2a 107.8 . . ?
C3 C2 N1 112.75(12) . . ?
C3 C2 H2a 109.04(8) . . ?
C3 C2 H2b 109.04(8) . . ?
N2 N3 C1 117.19(12) . . ?
C9 N3 C1 125.31(12) . . ?
C9 N3 N2 117.50(12) . . ?
C4 C3 C2 121.26(14) . . ?
C8 C3 C2 119.21(14) . . ?
C8 C3 C4 119.49(14) . . ?
H4 C4 C3 119.98(9) . . ?
C5 C4 C3 120.04(15) . . ?
C5 C4 H4 119.98(10) . . ?
H5 C5 C4 119.87(10) . . ?
C6 C5 C4 120.25(16) . . ?
C6 C5 H5 119.87(10) . . ?
H6 C6 C5 120.07(10) . . ?
C7 C6 C5 119.85(15) . . ?
C7 C6 H6 120.07(9) . . ?
H7 C7 C6 119.98(9) . . ?
C8 C7 C6 120.05(15) . . ?
C8 C7 H7 119.98(10) . . ?
C7 C8 C3 120.31(16) . . ?
H8 C8 C3 119.85(9) . . ?
H8 C8 C7 119.85(10) . . ?
H9a C9 N3 109.5 . . ?
H9b C9 N3 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 N3 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 N1 N2 N3 -1.23(10) . . . . ?
P1 N1 C2 C3 145.79(12) . . . . ?
P1 C1 N3 N2 -0.49(12) . . . . ?
P1 C1 N3 C9 178.98(9) . . . . ?
N1 N2 N3 C1 1.06(13) . . . . ?
N1 N2 N3 C9 -178.45(11) . . . . ?
N1 C2 C3 C4 -60.48(15) . . . . ?
N1 C2 C3 C8 121.58(13) . . . . ?
C2 C3 C4 C5 -176.89(14) . . . . ?
C2 C3 C8 C7 177.25(13) . . . . ?
C3 C4 C5 C6 -0.58(18) . . . . ?
C3 C8 C7 C6 -0.08(17) . . . . ?
C4 C5 C6 C7 -0.24(19) . . . . ?
C5 C6 C7 C8 0.56(18) . . . . ?


_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_NL1078
_database_code_depnum_ccdc_archive 'CCDC 2279456'
loop_
_audit_author_name
_audit_author_address
'Manuela Weber'
;Freie Universitaet Berlin, Institut fuer Chemie und Biochemie, Anorganische Chemie
Germany
;
_audit_update_record             
;
2023-07-06 deposited with the CCDC.	2023-07-25 downloaded from the CCDC.
;
_audit_creation_date             2023-07-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_chemical_formula_moiety         'C21 H37 B N3 P'
_chemical_formula_sum            'C21 H37 B N3 P'
_chemical_formula_weight         373.346
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
B 0.00963 0.00408 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.19320 '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 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 '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 0.00304 '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 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 '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'
P 0.30359 0.43700 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11490 '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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   14.06027(9)
_cell_length_b                   23.24206(15)
_cell_length_c                   14.36186(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.7284(2)
_cell_angle_gamma                90
_cell_volume                     4577.97(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9948
_cell_measurement_temperature    102.60
_cell_measurement_theta_max      74.56
_cell_measurement_theta_min      3.22
_exptl_absorpt_coefficient_mu    1.110
_exptl_absorpt_correction_T_max  0.8406
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1199 before and 0.0560 after correction.
The Ratio of minimum to maximum transmission is 0.8440.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.083
_exptl_crystal_description       plate
_exptl_crystal_F_000             1638.560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.9993
_diffrn_reflns_Laue_measured_fraction_max 0.9975
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            78829
_diffrn_reflns_point_group_measured_fraction_full 0.9993
_diffrn_reflns_point_group_measured_fraction_max 0.9975
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         74.66
_diffrn_reflns_theta_min         3.22
_diffrn_ambient_temperature      102.60
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                8729
_reflns_number_total             9356
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.3528
_refine_diff_density_min         -0.2408
_refine_diff_density_rms         0.0381
_refine_ls_d_res_high            0.7994
_refine_ls_d_res_low             13.7147
_refine_ls_goodness_of_fit_ref   1.0328
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    108
_refine_ls_number_parameters     485
_refine_ls_number_reflns         9356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0327
_refine_ls_restrained_S_all      1.0328
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+1.4546P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0896
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C8(H8), C11(H11), C8B(H8B), C11B(H11B)
1.b Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C16(H16a,H16b), C18(H18a,H18b), C20(H20a,H20b), C14B(H14c,
 H14d), C16B(H16c,H16d), C18B(H18c,H18d), C20B(H20c,H20d)
1.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C4B(H4B), C5B(H5B), C6B(H6B)
1.d Idealised Me refined as rotating group:
 C9(H9a,H9b,H9c), C10(H10a,H10b,H10c), C12(H12a,H12b,H12c), C13(H13a,H13b,
 H13c), C15(H15a,H15b,H15c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c), C21(H21a,
 H21b,H21c), C9B(H9Ba,H9Bb,H9Bc), C10B(H10d,H10e,H10f), C12B(H12d,H12e,H12f),
 C13B(H13d,H13e,H13f), C15B(H15d,H15e,H15f), C17B(H17d,H17e,H17f), C19B(H19d,
 H19e,H19f), C21B(H21d,H21e,H21f)
;
_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
P1 P 0.360394(19) 0.609308(11) 0.759804(19) 0.02036(7) Uani 1.000000 .
N1 N 0.42764(6) 0.56190(4) 0.70965(6) 0.01767(17) Uani 1.000000 .
N2 N 0.51156(6) 0.58018(4) 0.69486(6) 0.01870(17) Uani 1.000000 .
N3 N 0.52249(6) 0.63434(4) 0.72543(6) 0.01807(17) Uani 1.000000 .
C1 C 0.45171(7) 0.65964(4) 0.76272(7) 0.01852(19) Uani 1.000000 .
C2 C 0.39796(7) 0.50443(4) 0.67485(7) 0.01832(19) Uani 1.000000 .
C3 C 0.41437(7) 0.45869(4) 0.73935(7) 0.0194(2) Uani 1.000000 .
C4 C 0.38043(8) 0.40466(5) 0.70433(8) 0.0236(2) Uani 1.000000 .
H4 H 0.38947(8) 0.37243(5) 0.74606(8) 0.0284(3) Uiso 1.000000 R
C5 C 0.33374(8) 0.39749(5) 0.60946(8) 0.0266(2) Uani 1.000000 .
H5 H 0.31063(8) 0.36053(5) 0.58687(8) 0.0319(3) Uiso 1.000000 R
C6 C 0.32054(8) 0.44381(5) 0.54743(8) 0.0252(2) Uani 1.000000 .
H6 H 0.28910(8) 0.43798(5) 0.48247(8) 0.0302(3) Uiso 1.000000 R
C7 C 0.35236(7) 0.49887(5) 0.57811(7) 0.0211(2) Uani 1.000000 .
C8 C 0.46545(8) 0.46611(4) 0.84361(7) 0.0211(2) Uani 1.000000 .
H8 H 0.49450(8) 0.50556(4) 0.85166(7) 0.0253(2) Uiso 1.000000 R
C9 C 0.54806(9) 0.42244(5) 0.87377(8) 0.0284(2) Uani 1.000000 .
H9a H 0.52071(10) 0.38352(6) 0.8706(6) 0.0426(4) Uiso 1.000000 GR
H9b H 0.5931(4) 0.4252(3) 0.8307(4) 0.0426(4) Uiso 1.000000 GR
H9c H 0.5832(4) 0.4306(3) 0.9393(2) 0.0426(4) Uiso 1.000000 GR
C10 C 0.39193(9) 0.46130(6) 0.90758(8) 0.0305(3) Uani 1.000000 .
H10a H 0.3428(4) 0.4917(3) 0.8909(5) 0.0457(4) Uiso 1.000000 GR
H10b H 0.3600(5) 0.42362(17) 0.8983(5) 0.0457(4) Uiso 1.000000 GR
H10c H 0.42596(14) 0.4655(4) 0.97453(9) 0.0457(4) Uiso 1.000000 GR
C11 C 0.33424(8) 0.54972(5) 0.50969(8) 0.0255(2) Uani 1.000000 .
H11 H 0.37228(8) 0.58325(5) 0.54206(8) 0.0306(3) Uiso 1.000000 R
C12 C 0.36756(13) 0.53794(7) 0.41731(10) 0.0503(4) Uani 1.000000 .
H12a H 0.3290(6) 0.5063(4) 0.3828(4) 0.0754(6) Uiso 1.000000 GR
H12b H 0.3583(9) 0.57261(18) 0.3775(4) 0.0754(6) Uiso 1.000000 GR
H12c H 0.4367(3) 0.5273(5) 0.43235(11) 0.0754(6) Uiso 1.000000 GR
C13 C 0.22627(10) 0.56577(6) 0.48843(10) 0.0409(3) Uani 1.000000 .
H13a H 0.21532(17) 0.5995(3) 0.4466(7) 0.0613(5) Uiso 1.000000 GR
H13b H 0.18742(11) 0.53344(19) 0.4568(7) 0.0613(5) Uiso 1.000000 GR
H13c H 0.2068(2) 0.5746(5) 0.54830(13) 0.0613(5) Uiso 1.000000 GR
C14 C 0.61067(8) 0.66255(5) 0.70603(8) 0.0239(2) Uani 1.000000 .
H14a H 0.62359(8) 0.69878(5) 0.74289(8) 0.0286(3) Uiso 1.000000 R
H14b H 0.66782(8) 0.63698(5) 0.72617(8) 0.0286(3) Uiso 1.000000 R
C15 C 0.59523(9) 0.67530(5) 0.60045(9) 0.0316(3) Uani 1.000000 .
H15a H 0.5838(7) 0.63924(7) 0.56435(10) 0.0474(4) Uiso 1.000000 GR
H15b H 0.5386(4) 0.7006(3) 0.58086(17) 0.0474(4) Uiso 1.000000 GR
H15c H 0.6533(3) 0.6943(4) 0.58775(13) 0.0474(4) Uiso 1.000000 GR
C16 C 0.54520(8) 0.73613(5) 0.89185(7) 0.0241(2) Uani 1.000000 .
H16a H 0.53818(8) 0.77417(5) 0.92062(7) 0.0289(3) Uiso 1.000000 R
H16b H 0.60389(8) 0.73784(5) 0.86447(7) 0.0289(3) Uiso 1.000000 R
C17 C 0.56283(9) 0.69119(5) 0.97148(8) 0.0314(3) Uani 1.000000 .
H17a H 0.5735(7) 0.65350(9) 0.94492(15) 0.0471(4) Uiso 1.000000 GR
H17b H 0.6205(4) 0.7019(2) 1.0203(3) 0.0471(4) Uiso 1.000000 GR
H17c H 0.5059(3) 0.6893(3) 1.0003(5) 0.0471(4) Uiso 1.000000 GR
C18 C 0.34755(8) 0.72912(5) 0.84237(8) 0.0237(2) Uani 1.000000 .
H18a H 0.35228(8) 0.70191(5) 0.89624(8) 0.0285(3) Uiso 1.000000 R
H18b H 0.29332(8) 0.71600(5) 0.79043(8) 0.0285(3) Uiso 1.000000 R
C19 C 0.32179(9) 0.78880(5) 0.87535(9) 0.0309(2) Uani 1.000000 .
H19a H 0.3107(7) 0.81545(11) 0.82115(17) 0.0463(4) Uiso 1.000000 GR
H19b H 0.2625(4) 0.78610(9) 0.9005(6) 0.0463(4) Uiso 1.000000 GR
H19c H 0.3757(3) 0.80295(18) 0.9255(5) 0.0463(4) Uiso 1.000000 GR
C20 C 0.44893(8) 0.77290(4) 0.71925(7) 0.0218(2) Uani 1.000000 .
H20a H 0.50933(8) 0.76794(4) 0.69539(7) 0.0262(2) Uiso 1.000000 R
H20b H 0.45094(8) 0.81185(4) 0.74749(7) 0.0262(2) Uiso 1.000000 R
C21 C 0.36173(9) 0.76998(5) 0.63386(8) 0.0289(2) Uani 1.000000 .
H21a H 0.3677(4) 0.8003(3) 0.5881(3) 0.0434(4) Uiso 1.000000 GR
H21b H 0.3605(4) 0.73234(16) 0.6029(4) 0.0434(4) Uiso 1.000000 GR
H21c H 0.30121(10) 0.7754(4) 0.65600(12) 0.0434(4) Uiso 1.000000 GR
B1 B 0.44964(9) 0.72561(5) 0.80404(8) 0.0198(2) Uani 1.000000 .
P1B P 0.88960(2) 0.610181(11) 0.658869(19) 0.02268(7) Uani 1.000000 .
N1B N 0.94804(6) 0.57139(4) 0.75591(6) 0.02021(18) Uani 1.000000 .
N2B N 1.01341(7) 0.59862(4) 0.82030(7) 0.02326(19) Uani 1.000000 .
N3B N 1.01763(6) 0.65246(4) 0.79037(6) 0.02294(19) Uani 1.000000 .
C1B C 0.95860(7) 0.66888(5) 0.70528(7) 0.0219(2) Uani 1.000000 .
C2B C 0.92638(7) 0.51234(4) 0.77642(7) 0.0203(2) Uani 1.000000 .
C3B C 0.86350(7) 0.50340(4) 0.83819(8) 0.0217(2) Uani 1.000000 .
C4B C 0.83756(8) 0.44649(5) 0.85183(8) 0.0271(2) Uani 1.000000 .
H4B H 0.79507(8) 0.43845(5) 0.89326(8) 0.0325(3) Uiso 1.000000 R
C5B C 0.87292(9) 0.40177(5) 0.80582(9) 0.0311(3) Uani 1.000000 .
H5B H 0.85343(9) 0.36341(5) 0.81490(9) 0.0373(3) Uiso 1.000000 R
C6B C 0.93648(9) 0.41230(5) 0.74660(8) 0.0297(2) Uani 1.000000 .
H6B H 0.96052(9) 0.38088(5) 0.71625(8) 0.0357(3) Uiso 1.000000 R
C7B C 0.96599(8) 0.46801(5) 0.73052(8) 0.0242(2) Uani 1.000000 .
C8B C 0.82732(8) 0.55208(5) 0.89188(8) 0.0246(2) Uani 1.000000 .
H8B H 0.84008(8) 0.58916(5) 0.86149(8) 0.0295(3) Uiso 1.000000 R
C9B C 0.88451(11) 0.55292(6) 0.99574(10) 0.0419(3) Uani 1.000000 .
H9Ba H 0.95387(16) 0.5590(5) 0.99752(10) 0.0629(5) Uiso 1.000000 GR
H9Bb H 0.8604(6) 0.5842(3) 1.0300(2) 0.0629(5) Uiso 1.000000 GR
H9Bc H 0.8759(7) 0.51612(19) 1.0262(3) 0.0629(5) Uiso 1.000000 GR
C10B C 0.71776(9) 0.54791(6) 0.88644(10) 0.0352(3) Uani 1.000000 .
H10d H 0.68320(11) 0.5437(4) 0.81966(12) 0.0528(4) Uiso 1.000000 GR
H10e H 0.70439(12) 0.5145(3) 0.9231(6) 0.0528(4) Uiso 1.000000 GR
H10f H 0.69543(16) 0.5829(2) 0.9131(7) 0.0528(4) Uiso 1.000000 GR
C11B C 1.04189(8) 0.47977(5) 0.67187(8) 0.0298(2) Uani 1.000000 .
H11B H 1.02515(8) 0.51716(5) 0.63775(8) 0.0357(3) Uiso 1.000000 R
C12B C 1.14281(9) 0.48605(7) 0.73878(10) 0.0406(3) Uani 1.000000 .
H12d H 1.19118(16) 0.4951(5) 0.70116(13) 0.0609(5) Uiso 1.000000 GR
H12e H 1.1411(2) 0.5172(3) 0.7844(5) 0.0609(5) Uiso 1.000000 GR
H12f H 1.1606(4) 0.44993(17) 0.7734(6) 0.0609(5) Uiso 1.000000 GR
C13B C 1.04642(10) 0.43350(7) 0.59721(10) 0.0430(3) Uani 1.000000 .
H13d H 0.98127(19) 0.4278(4) 0.5567(5) 0.0645(5) Uiso 1.000000 GR
H13e H 1.0914(7) 0.4457(2) 0.5577(5) 0.0645(5) Uiso 1.000000 GR
H13f H 1.0695(8) 0.39731(15) 0.62940(10) 0.0645(5) Uiso 1.000000 GR
C14B C 1.08614(9) 0.69107(5) 0.85626(9) 0.0334(3) Uani 1.000000 .
H14c H 1.04782(9) 0.72003(5) 0.88286(9) 0.0401(3) Uiso 1.000000 R
H14d H 1.12698(9) 0.71189(5) 0.81928(9) 0.0401(3) Uiso 1.000000 R
C15B C 1.15146(9) 0.65980(5) 0.93709(8) 0.0316(3) Uani 1.000000 .
H15d H 1.1895(5) 0.6309(3) 0.91144(8) 0.0474(4) Uiso 1.000000 GR
H15e H 1.1958(5) 0.68730(8) 0.9764(4) 0.0474(4) Uiso 1.000000 GR
H15f H 1.11178(10) 0.6408(4) 0.9762(4) 0.0474(4) Uiso 1.000000 GR
C16B C 1.06012(8) 0.74552(5) 0.62719(9) 0.0291(2) Uani 1.000000 .
H16c H 1.10607(8) 0.75541(5) 0.68780(9) 0.0349(3) Uiso 1.000000 R
H16d H 1.05336(8) 0.77997(5) 0.58572(9) 0.0349(3) Uiso 1.000000 R
C17B C 1.10532(10) 0.69742(6) 0.57888(12) 0.0442(3) Uani 1.000000 .
H17d H 1.0585(3) 0.6847(3) 0.5215(5) 0.0663(5) Uiso 1.000000 GR
H17e H 1.1645(5) 0.71167(16) 0.5611(8) 0.0663(5) Uiso 1.000000 GR
H17f H 1.1219(8) 0.6650(2) 0.6230(3) 0.0663(5) Uiso 1.000000 GR
C18B C 0.87044(8) 0.72370(5) 0.55011(8) 0.0273(2) Uani 1.000000 .
H18c H 0.81004(8) 0.70808(5) 0.56511(8) 0.0327(3) Uiso 1.000000 R
H18d H 0.89460(8) 0.69510(5) 0.50975(8) 0.0327(3) Uiso 1.000000 R
C19B C 0.84542(10) 0.77937(6) 0.49277(9) 0.0376(3) Uani 1.000000 .
H19d H 0.90435(19) 0.7947(3) 0.4759(7) 0.0564(4) Uiso 1.000000 GR
H19e H 0.7963(6) 0.77130(11) 0.4344(4) 0.0564(4) Uiso 1.000000 GR
H19f H 0.8196(7) 0.80770(17) 0.5313(3) 0.0564(4) Uiso 1.000000 GR
C20B C 0.91950(9) 0.78199(5) 0.71697(9) 0.0300(2) Uani 1.000000 .
H20c H 0.92233(9) 0.81948(5) 0.68494(9) 0.0360(3) Uiso 1.000000 R
H20d H 0.96753(9) 0.78334(5) 0.77874(9) 0.0360(3) Uiso 1.000000 R
C21B C 0.81739(10) 0.77515(6) 0.73731(10) 0.0397(3) Uani 1.000000 .
H21d H 0.76828(11) 0.7780(5) 0.67737(14) 0.0596(4) Uiso 1.000000 GR
H21e H 0.8123(3) 0.7375(2) 0.7665(7) 0.0596(4) Uiso 1.000000 GR
H21f H 0.8064(3) 0.8056(3) 0.7810(6) 0.0596(4) Uiso 1.000000 GR
B1B B 0.95302(9) 0.73147(5) 0.65086(9) 0.0240(2) Uani 1.000000 .


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
P1 N1 1.7110(8) . ?
P1 C1 1.7306(10) . ?
N1 N2 1.3146(12) . ?
N1 C2 1.4546(12) . ?
N2 N3 1.3310(12) . ?
N3 C1 1.3629(13) . ?
N3 C14 1.4822(13) . ?
C1 B1 1.6468(15) . ?
C2 C3 1.3955(14) . ?
C2 C7 1.4021(14) . ?
C3 C4 1.3971(14) . ?
C3 C8 1.5211(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3861(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3835(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3946(15) . ?
C7 C11 1.5221(15) . ?
C8 H8 1.0000 . ?
C8 C9 1.5315(15) . ?
C8 C10 1.5310(15) . ?
C9 H9a 0.9800 . ?
C9 H9b 0.9800 . ?
C9 H9c 0.9800 . ?
C10 H10a 0.9800 . ?
C10 H10b 0.9800 . ?
C10 H10c 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.5260(17) . ?
C11 C13 1.5274(16) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
C14 H14a 0.9900 . ?
C14 H14b 0.9900 . ?
C14 C15 1.5130(16) . ?
C15 H15a 0.9800 . ?
C15 H15b 0.9800 . ?
C15 H15c 0.9800 . ?
C16 H16a 0.9900 . ?
C16 H16b 0.9900 . ?
C16 C17 1.5280(15) . ?
C16 B1 1.6459(15) . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
C18 H18a 0.9900 . ?
C18 H18b 0.9900 . ?
C18 C19 1.5347(15) . ?
C18 B1 1.6487(15) . ?
C19 H19a 0.9800 . ?
C19 H19b 0.9800 . ?
C19 H19c 0.9800 . ?
C20 H20a 0.9900 . ?
C20 H20b 0.9900 . ?
C20 C21 1.5327(14) . ?
C20 B1 1.6387(15) . ?
C21 H21a 0.9800 . ?
C21 H21b 0.9800 . ?
C21 H21c 0.9800 . ?
P1B N1B 1.7105(9) . ?
P1B C1B 1.7210(10) . ?
N1B N2B 1.3137(12) . ?
N1B C2B 1.4501(13) . ?
N2B N3B 1.3289(13) . ?
N3B C1B 1.3716(14) . ?
N3B C14B 1.4923(13) . ?
C1B B1B 1.6450(16) . ?
C2B C3B 1.3990(15) . ?
C2B C7B 1.4029(15) . ?
C3B C4B 1.3972(15) . ?
C3B C8B 1.5188(15) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.3818(17) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.3845(18) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.3942(16) . ?
C7B C11B 1.5229(16) . ?
C8B H8B 1.0000 . ?
C8B C9B 1.5307(17) . ?
C8B C10B 1.5282(16) . ?
C9B H9Ba 0.9800 . ?
C9B H9Bb 0.9800 . ?
C9B H9Bc 0.9800 . ?
C10B H10d 0.9800 . ?
C10B H10e 0.9800 . ?
C10B H10f 0.9800 . ?
C11B H11B 1.0000 . ?
C11B C12B 1.5354(17) . ?
C11B C13B 1.5298(17) . ?
C12B H12d 0.9800 . ?
C12B H12e 0.9800 . ?
C12B H12f 0.9800 . ?
C13B H13d 0.9800 . ?
C13B H13e 0.9800 . ?
C13B H13f 0.9800 . ?
C14B H14c 0.9900 . ?
C14B H14d 0.9900 . ?
C14B C15B 1.4998(17) . ?
C15B H15d 0.9800 . ?
C15B H15e 0.9800 . ?
C15B H15f 0.9800 . ?
C16B H16c 0.9900 . ?
C16B H16d 0.9900 . ?
C16B C17B 1.5261(18) . ?
C16B B1B 1.6479(16) . ?
C17B H17d 0.9800 . ?
C17B H17e 0.9800 . ?
C17B H17f 0.9800 . ?
C18B H18c 0.9900 . ?
C18B H18d 0.9900 . ?
C18B C19B 1.5325(17) . ?
C18B B1B 1.6536(16) . ?
C19B H19d 0.9800 . ?
C19B H19e 0.9800 . ?
C19B H19f 0.9800 . ?
C20B H20c 0.9900 . ?
C20B H20d 0.9900 . ?
C20B C21B 1.5352(18) . ?
C20B B1B 1.6430(17) . ?
C21B H21d 0.9800 . ?
C21B H21e 0.9800 . ?
C21B H21f 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 N1 88.26(4) . . ?
N2 N1 P1 117.31(7) . . ?
C2 N1 P1 126.35(7) . . ?
C2 N1 N2 116.17(8) . . ?
N3 N2 N1 107.15(8) . . ?
C1 N3 N2 119.77(8) . . ?
C14 N3 N2 113.38(8) . . ?
C14 N3 C1 126.62(9) . . ?
N3 C1 P1 107.51(7) . . ?
B1 C1 P1 124.48(7) . . ?
B1 C1 N3 128.00(9) . . ?
C3 C2 N1 118.59(9) . . ?
C7 C2 N1 117.33(9) . . ?
C7 C2 C3 124.07(9) . . ?
C4 C3 C2 116.90(9) . . ?
C8 C3 C2 122.69(9) . . ?
C8 C3 C4 120.40(9) . . ?
H4 C4 C3 119.60(6) . . ?
C5 C4 C3 120.80(10) . . ?
C5 C4 H4 119.60(7) . . ?
H5 C5 C4 119.77(7) . . ?
C6 C5 C4 120.45(10) . . ?
C6 C5 H5 119.77(6) . . ?
H6 C6 C5 119.25(6) . . ?
C7 C6 C5 121.49(10) . . ?
C7 C6 H6 119.25(6) . . ?
C6 C7 C2 116.26(10) . . ?
C11 C7 C2 122.89(9) . . ?
C11 C7 C6 120.80(9) . . ?
H8 C8 C3 108.07(5) . . ?
C9 C8 C3 111.56(9) . . ?
C9 C8 H8 108.07(6) . . ?
C10 C8 C3 110.35(9) . . ?
C10 C8 H8 108.07(6) . . ?
C10 C8 C9 110.61(9) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H10a C10 C8 109.5 . . ?
H10b C10 C8 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C8 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
H11 C11 C7 107.98(6) . . ?
C12 C11 C7 112.47(10) . . ?
C12 C11 H11 107.98(9) . . ?
C13 C11 C7 109.66(10) . . ?
C13 C11 H11 107.98(7) . . ?
C13 C11 C12 110.61(11) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14a C14 N3 109.77(5) . . ?
H14b C14 N3 109.77(5) . . ?
H14b C14 H14a 108.2 . . ?
C15 C14 N3 109.50(9) . . ?
C15 C14 H14a 109.77(6) . . ?
C15 C14 H14b 109.77(6) . . ?
H15a C15 C14 109.5 . . ?
H15b C15 C14 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C14 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H16b C16 H16a 107.4 . . ?
C17 C16 H16a 108.22(6) . . ?
C17 C16 H16b 108.22(7) . . ?
B1 C16 H16a 108.22(6) . . ?
B1 C16 H16b 108.22(5) . . ?
B1 C16 C17 116.26(9) . . ?
H17a C17 C16 109.5 . . ?
H17b C17 C16 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 C16 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
H18b C18 H18a 107.5 . . ?
C19 C18 H18a 108.41(6) . . ?
C19 C18 H18b 108.41(6) . . ?
B1 C18 H18a 108.41(6) . . ?
B1 C18 H18b 108.41(5) . . ?
B1 C18 C19 115.45(9) . . ?
H19a C19 C18 109.5 . . ?
H19b C19 C18 109.5 . . ?
H19b C19 H19a 109.5 . . ?
H19c C19 C18 109.5 . . ?
H19c C19 H19a 109.5 . . ?
H19c C19 H19b 109.5 . . ?
H20b C20 H20a 107.4 . . ?
C21 C20 H20a 108.29(6) . . ?
C21 C20 H20b 108.29(6) . . ?
B1 C20 H20a 108.29(6) . . ?
B1 C20 H20b 108.29(5) . . ?
B1 C20 C21 115.96(9) . . ?
H21a C21 C20 109.5 . . ?
H21b C21 C20 109.5 . . ?
H21b C21 H21a 109.5 . . ?
H21c C21 C20 109.5 . . ?
H21c C21 H21a 109.5 . . ?
H21c C21 H21b 109.5 . . ?
C16 B1 C1 109.76(8) . . ?
C18 B1 C1 104.60(8) . . ?
C18 B1 C16 111.14(8) . . ?
C20 B1 C1 110.75(8) . . ?
C20 B1 C16 109.89(8) . . ?
C20 B1 C18 110.60(9) . . ?
C1B P1B N1B 88.49(5) . . ?
N2B N1B P1B 117.11(7) . . ?
C2B N1B P1B 125.43(7) . . ?
C2B N1B N2B 117.30(8) . . ?
N3B N2B N1B 107.47(8) . . ?
C1B N3B N2B 119.27(9) . . ?
C14B N3B N2B 115.46(9) . . ?
C14B N3B C1B 125.25(9) . . ?
N3B C1B P1B 107.66(8) . . ?
B1B C1B P1B 123.59(8) . . ?
B1B C1B N3B 128.72(9) . . ?
C3B C2B N1B 117.37(9) . . ?
C7B C2B N1B 118.48(9) . . ?
C7B C2B C3B 124.10(10) . . ?
C4B C3B C2B 116.77(10) . . ?
C8B C3B C2B 122.72(9) . . ?
C8B C3B C4B 120.46(10) . . ?
H4B C4B C3B 119.59(7) . . ?
C5B C4B C3B 120.83(11) . . ?
C5B C4B H4B 119.59(7) . . ?
H5B C5B C4B 119.68(7) . . ?
C6B C5B C4B 120.64(11) . . ?
C6B C5B H5B 119.68(7) . . ?
H6B C6B C5B 119.27(7) . . ?
C7B C6B C5B 121.46(11) . . ?
C7B C6B H6B 119.27(7) . . ?
C6B C7B C2B 116.15(10) . . ?
C11B C7B C2B 121.82(10) . . ?
C11B C7B C6B 121.92(10) . . ?
H8B C8B C3B 107.94(6) . . ?
C9B C8B C3B 109.97(9) . . ?
C9B C8B H8B 107.94(7) . . ?
C10B C8B C3B 111.93(10) . . ?
C10B C8B H8B 107.94(6) . . ?
C10B C8B C9B 110.97(10) . . ?
H9Ba C9B C8B 109.5 . . ?
H9Bb C9B C8B 109.5 . . ?
H9Bb C9B H9Ba 109.5 . . ?
H9Bc C9B C8B 109.5 . . ?
H9Bc C9B H9Ba 109.5 . . ?
H9Bc C9B H9Bb 109.5 . . ?
H10d C10B C8B 109.5 . . ?
H10e C10B C8B 109.5 . . ?
H10e C10B H10d 109.5 . . ?
H10f C10B C8B 109.5 . . ?
H10f C10B H10d 109.5 . . ?
H10f C10B H10e 109.5 . . ?
H11B C11B C7B 108.01(6) . . ?
C12B C11B C7B 109.54(10) . . ?
C12B C11B H11B 108.01(8) . . ?
C13B C11B C7B 113.83(11) . . ?
C13B C11B H11B 108.01(8) . . ?
C13B C11B C12B 109.27(10) . . ?
H12d C12B C11B 109.5 . . ?
H12e C12B C11B 109.5 . . ?
H12e C12B H12d 109.5 . . ?
H12f C12B C11B 109.5 . . ?
H12f C12B H12d 109.5 . . ?
H12f C12B H12e 109.5 . . ?
H13d C13B C11B 109.5 . . ?
H13e C13B C11B 109.5 . . ?
H13e C13B H13d 109.5 . . ?
H13f C13B C11B 109.5 . . ?
H13f C13B H13d 109.5 . . ?
H13f C13B H13e 109.5 . . ?
H14c C14B N3B 108.86(7) . . ?
H14d C14B N3B 108.86(6) . . ?
H14d C14B H14c 107.7 . . ?
C15B C14B N3B 113.52(10) . . ?
C15B C14B H14c 108.86(7) . . ?
C15B C14B H14d 108.86(7) . . ?
H15d C15B C14B 109.5 . . ?
H15e C15B C14B 109.5 . . ?
H15e C15B H15d 109.5 . . ?
H15f C15B C14B 109.5 . . ?
H15f C15B H15d 109.5 . . ?
H15f C15B H15e 109.5 . . ?
H16d C16B H16c 107.4 . . ?
C17B C16B H16c 108.27(8) . . ?
C17B C16B H16d 108.27(7) . . ?
B1B C16B H16c 108.27(6) . . ?
B1B C16B H16d 108.27(6) . . ?
B1B C16B C17B 116.08(10) . . ?
H17d C17B C16B 109.5 . . ?
H17e C17B C16B 109.5 . . ?
H17e C17B H17d 109.5 . . ?
H17f C17B C16B 109.5 . . ?
H17f C17B H17d 109.5 . . ?
H17f C17B H17e 109.5 . . ?
H18d C18B H18c 107.6 . . ?
C19B C18B H18c 108.68(7) . . ?
C19B C18B H18d 108.68(7) . . ?
B1B C18B H18c 108.68(6) . . ?
B1B C18B H18d 108.68(6) . . ?
B1B C18B C19B 114.32(10) . . ?
H19d C19B C18B 109.5 . . ?
H19e C19B C18B 109.5 . . ?
H19e C19B H19d 109.5 . . ?
H19f C19B C18B 109.5 . . ?
H19f C19B H19d 109.5 . . ?
H19f C19B H19e 109.5 . . ?
H20d C20B H20c 107.4 . . ?
C21B C20B H20c 108.33(7) . . ?
C21B C20B H20d 108.33(7) . . ?
B1B C20B H20c 108.33(6) . . ?
B1B C20B H20d 108.33(6) . . ?
B1B C20B C21B 115.80(10) . . ?
H21d C21B C20B 109.5 . . ?
H21e C21B C20B 109.5 . . ?
H21e C21B H21d 109.5 . . ?
H21f C21B C20B 109.5 . . ?
H21f C21B H21d 109.5 . . ?
H21f C21B H21e 109.5 . . ?
C16B B1B C1B 108.86(9) . . ?
C18B B1B C1B 105.66(9) . . ?
C18B B1B C16B 109.78(9) . . ?
C20B B1B C1B 110.32(9) . . ?
C20B B1B C16B 111.66(9) . . ?
C20B B1B C18B 110.37(9) . . ?

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
P1 N1 N2 N3 0.29(7) . . . . ?
P1 N1 C2 C3 -86.23(9) . . . . ?
P1 N1 C2 C7 92.40(9) . . . . ?
P1 C1 N3 N2 0.37(8) . . . . ?
P1 C1 N3 C14 174.42(6) . . . . ?
P1 C1 B1 C16 121.34(8) . . . . ?
P1 C1 B1 C18 2.03(8) . . . . ?
P1 C1 B1 C20 -117.15(8) . . . . ?
N1 N2 N3 C1 -0.42(9) . . . . ?
N1 N2 N3 C14 -175.23(8) . . . . ?
N1 C2 C3 C4 176.85(9) . . . . ?
N1 C2 C3 C8 -2.39(11) . . . . ?
N1 C2 C7 C6 -177.14(9) . . . . ?
N1 C2 C7 C11 0.62(11) . . . . ?
N2 N3 C1 B1 -179.70(8) . . . . ?
N2 N3 C14 C15 72.62(9) . . . . ?
N3 C1 B1 C16 -58.58(11) . . . . ?
N3 C1 B1 C18 -177.90(11) . . . . ?
N3 C1 B1 C20 62.93(11) . . . . ?
C1 B1 C16 C17 -51.18(10) . . . . ?
C1 B1 C18 C19 -173.75(8) . . . . ?
C1 B1 C20 C21 60.81(10) . . . . ?
C2 C3 C4 C5 0.69(11) . . . . ?
C2 C3 C8 C9 -129.56(10) . . . . ?
C2 C3 C8 C10 107.06(11) . . . . ?
C2 C7 C6 C5 -0.13(11) . . . . ?
C2 C7 C11 C12 131.05(12) . . . . ?
C2 C7 C11 C13 -105.42(11) . . . . ?
C3 C4 C5 C6 0.48(13) . . . . ?
C4 C5 C6 C7 -0.78(13) . . . . ?
C5 C6 C7 C11 -177.94(10) . . . . ?
C6 C7 C11 C12 -51.28(13) . . . . ?
C6 C7 C11 C13 72.24(12) . . . . ?
C16 B1 C18 C19 67.87(10) . . . . ?
C16 B1 C20 C21 -177.76(9) . . . . ?
C18 B1 C20 C21 -54.69(10) . . . . ?
P1B N1B N2B N3B -0.64(8) . . . . ?
P1B N1B C2B C3B -95.65(9) . . . . ?
P1B N1B C2B C7B 81.73(9) . . . . ?
P1B C1B N3B N2B 0.68(9) . . . . ?
P1B C1B N3B C14B -177.18(8) . . . . ?
P1B C1B B1B C16B -117.26(9) . . . . ?
P1B C1B B1B C18B 0.59(9) . . . . ?
P1B C1B B1B C20B 119.89(9) . . . . ?
N1B N2B N3B C1B -0.06(10) . . . . ?
N1B N2B N3B C14B 178.01(9) . . . . ?
N1B C2B C3B C4B 175.43(9) . . . . ?
N1B C2B C3B C8B -7.00(11) . . . . ?
N1B C2B C7B C6B -174.88(9) . . . . ?
N1B C2B C7B C11B 9.00(11) . . . . ?
N2B N3B C1B B1B -177.31(9) . . . . ?
N2B N3B C14B C15B 10.17(10) . . . . ?
N3B C1B B1B C16B 60.44(12) . . . . ?
N3B C1B B1B C18B 178.29(12) . . . . ?
N3B C1B B1B C20B -62.41(12) . . . . ?
C1B B1B C16B C17B 49.25(11) . . . . ?
C1B B1B C18B C19B 173.64(9) . . . . ?
C1B B1B C20B C21B -62.91(11) . . . . ?
C2B C3B C4B C5B -0.08(12) . . . . ?
C2B C3B C8B C9B -101.80(12) . . . . ?
C2B C3B C8B C10B 134.37(11) . . . . ?
C2B C7B C6B C5B -0.99(12) . . . . ?
C2B C7B C11B C12B 80.48(12) . . . . ?
C2B C7B C11B C13B -156.87(11) . . . . ?
C3B C4B C5B C6B 1.30(13) . . . . ?
C4B C5B C6B C7B -0.74(14) . . . . ?
C5B C6B C7B C11B 175.12(11) . . . . ?
C6B C7B C11B C12B -95.42(12) . . . . ?
C6B C7B C11B C13B 27.24(12) . . . . ?
C16B B1B C18B C19B -69.13(11) . . . . ?
C16B B1B C20B C21B 175.90(10) . . . . ?
C18B B1B C20B C21B 53.49(11) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
