# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_RAH30
_database_code_depnum_ccdc_archive 'CCDC 2346139'
loop_
_audit_author_name
_audit_author_address
'Marie Cordier'
;Univ Rennes, CNRS, ISCR UMR, Rennes, France
France
;
_audit_update_record             
;
2024-05-29 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 15 novembre 2023                                         #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C38 H52 B2 F8 N4 O6 S2, 4(C H Cl3)'
_chemical_formula_sum            'C42 H56 B2 Cl12 F8 N4 O6 S2'
_chemical_formula_weight         1376.04
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   14.1344(16)
_cell_length_b                   11.0335(12)
_cell_length_c                   20.579(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.181(4)
_cell_angle_gamma                90
_cell_volume                     3031.2(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9889
_cell_measurement_theta_min      2.3948
_cell_measurement_theta_max      27.4307
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0150214
_diffrn_orient_matrix_UB_21      0.0633291
_diffrn_orient_matrix_UB_31      -0.0370810
_diffrn_orient_matrix_UB_12      0.0699623
_diffrn_orient_matrix_UB_22      -0.0405569
_diffrn_orient_matrix_UB_32      -0.0409241
_diffrn_orient_matrix_UB_13      -0.0259250
_diffrn_orient_matrix_UB_23      0.0001225
_diffrn_orient_matrix_UB_33      -0.0444417


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1404
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_T_max  0.854

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0294
_diffrn_reflns_av_r_equivalents  0.0374
_diffrn_reflns_number            32161
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.096
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             6937
_reflns_number_gt                5581
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  
'CRYSCALC (T. Roisnel, local program, ver. 2023)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0305P)²+2.1366P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6937
_refine_ls_number_parameters     446
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0936
_refine_ls_wR_factor_gt          0.0848
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.342
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.048

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
S1 S 0.79064(3) -0.19009(4) 0.07361(2) 0.02635(11) Uani 1 1 d . . . . .
F1 F 0.69991(7) 0.09553(9) 0.02124(5) 0.0252(2) Uani 1 1 d . . . . .
F2 F 0.71680(11) -0.13014(14) -0.05664(6) 0.0566(4) Uani 1 1 d . . . . .
F3 F 0.81388(12) -0.28585(14) -0.03482(7) 0.0656(4) Uani 1 1 d . . . . .
F4 F 0.87582(12) -0.10740(15) -0.01219(8) 0.0642(4) Uani 1 1 d . . . . .
O1 O 0.78977(9) -0.05965(10) 0.09417(6) 0.0254(3) Uani 1 1 d . . . . .
O2 O 0.69839(10) -0.25090(11) 0.06468(8) 0.0370(3) Uani 1 1 d . . . . .
O3 O 0.88166(10) -0.24532(12) 0.11423(7) 0.0387(3) Uani 1 1 d . . . . .
N1 N 0.74501(9) 0.12497(12) 0.14368(7) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.60922(10) -0.01666(12) 0.08142(7) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.79958(12) 0.23413(14) 0.13816(8) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.74428(12) 0.33962(15) 0.11299(8) 0.0227(3) Uani 1 1 d . . . . .
C3 C 0.79684(14) 0.44385(16) 0.10739(9) 0.0271(4) Uani 1 1 d . . . . .
H3 H 0.761192 0.516351 0.090102 0.033 Uiso 1 1 calc R U . . .
C4 C 0.90031(14) 0.44295(17) 0.12670(10) 0.0315(4) Uani 1 1 d . . . . .
H4 H 0.935176 0.514874 0.123046 0.038 Uiso 1 1 calc R U . . .
C5 C 0.95316(13) 0.33781(17) 0.15129(10) 0.0304(4) Uani 1 1 d . . . . .
H5 H 1.024160 0.338560 0.164219 0.037 Uiso 1 1 calc R U . . .
C6 C 0.90442(12) 0.23047(15) 0.15755(9) 0.0236(3) Uani 1 1 d . . . . .
C7 C 0.63032(12) 0.34339(15) 0.09110(9) 0.0265(4) Uani 1 1 d . . . . .
H7 H 0.606560 0.262821 0.101783 0.032 Uiso 1 1 calc R U . . .
C8 C 0.59377(15) 0.44055(18) 0.13051(11) 0.0360(4) Uani 1 1 d . . . . .
H8A H 0.612882 0.520879 0.118726 0.054 Uiso 1 1 calc R U . . .
H8B H 0.624364 0.426908 0.180084 0.054 Uiso 1 1 calc R U . . .
H8C H 0.520710 0.435979 0.117932 0.054 Uiso 1 1 calc R U . . .
C9 C 0.58457(14) 0.36485(17) 0.01358(10) 0.0340(4) Uani 1 1 d . . . . .
H9A H 0.604653 0.444925 0.002148 0.051 Uiso 1 1 calc R U . . .
H9B H 0.511377 0.361011 0.000124 0.051 Uiso 1 1 calc R U . . .
H9C H 0.608362 0.302375 -0.011168 0.051 Uiso 1 1 calc R U . . .
C10 C 0.96460(12) 0.11534(16) 0.18285(9) 0.0278(4) Uani 1 1 d . . . . .
H10 H 0.917127 0.050204 0.186031 0.033 Uiso 1 1 calc R U . . .
C11 C 1.01517(16) 0.0745(2) 0.13103(12) 0.0429(5) Uani 1 1 d . . . . .
H11A H 0.964918 0.068919 0.085105 0.064 Uiso 1 1 calc R U . . .
H11B H 1.046306 -0.004988 0.144578 0.064 Uiso 1 1 calc R U . . .
H11C H 1.066615 0.133556 0.130286 0.064 Uiso 1 1 calc R U . . .
C12 C 1.04327(14) 0.13107(19) 0.25409(11) 0.0387(5) Uani 1 1 d . . . . .
H12A H 1.089154 0.196773 0.252576 0.058 Uiso 1 1 calc R U . . .
H12B H 1.081102 0.055539 0.267679 0.058 Uiso 1 1 calc R U . . .
H12C H 1.009897 0.150964 0.287614 0.058 Uiso 1 1 calc R U . . .
C13 C 0.72239(12) 0.10374(14) 0.20085(8) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.65464(12) 0.01291(15) 0.20146(9) 0.0235(3) Uani 1 1 d . . . . .
H14 H 0.6413(14) -0.0038(18) 0.2424(10) 0.028 Uiso 1 1 d . U . . .
C15 C 0.59193(12) -0.03742(14) 0.14043(9) 0.0223(3) Uani 1 1 d . . . . .
C16 C 0.76443(14) 0.18368(16) 0.26262(9) 0.0275(4) Uani 1 1 d . . . . .
H16A H 0.837686 0.184540 0.276124 0.041 Uiso 1 1 calc R U . . .
H16B H 0.744350 0.152480 0.300735 0.041 Uiso 1 1 calc R U . . .
H16C H 0.738711 0.266251 0.251366 0.041 Uiso 1 1 calc R U . . .
C17 C 0.50281(14) -0.11038(18) 0.14119(10) 0.0319(4) Uani 1 1 d . . . . .
H17A H 0.441456 -0.071560 0.111517 0.048 Uiso 1 1 calc R U . . .
H17B H 0.500979 -0.114928 0.188320 0.048 Uiso 1 1 calc R U . . .
H17C H 0.507745 -0.192337 0.124229 0.048 Uiso 1 1 calc R U . . .
C18 C 0.53672(12) -0.05175(14) 0.01455(8) 0.0221(3) Uani 1 1 d . . . . .
H18A H 0.499509 -0.124729 0.020324 0.026 Uiso 1 1 calc R U . . .
H18B H 0.572747 -0.071745 -0.017976 0.026 Uiso 1 1 calc R U . . .
C19 C 0.80019(17) -0.1767(2) -0.01291(11) 0.0419(5) Uani 1 1 d . . . . .
B1 B 0.70615(13) 0.04064(16) 0.08225(9) 0.0200(4) Uani 1 1 d . . . . .
Cl1A Cl 0.4712(4) 0.2089(7) 0.2072(4) 0.0746(13) Uani 0.51(3) 1 d D . P A 1
Cl2A Cl 0.3264(6) 0.0722(5) 0.2460(4) 0.0729(12) Uani 0.51(3) 1 d D . P A 1
Cl3A Cl 0.2928(4) 0.3231(4) 0.2126(3) 0.0510(11) Uani 0.51(3) 1 d D . P A 1
C20A C 0.3836(4) 0.2135(5) 0.2495(4) 0.0413(6) Uani 0.51(3) 1 d D . P A 1
H20A H 0.418481 0.235155 0.298746 0.050 Uiso 0.51(3) 1 calc R U P A 1
Cl1B Cl 0.4783(5) 0.2331(14) 0.2162(6) 0.0768(18) Uani 0.49(3) 1 d D . P A 2
Cl2B Cl 0.3448(11) 0.0673(5) 0.2471(3) 0.0765(15) Uani 0.49(3) 1 d D . P A 2
Cl3B Cl 0.2876(5) 0.3157(6) 0.2186(5) 0.0775(18) Uani 0.49(3) 1 d D . P A 2
C20B C 0.3874(5) 0.2169(5) 0.2551(4) 0.0413(6) Uani 0.49(3) 1 d D . P A 2
H20B H 0.417811 0.236555 0.305147 0.050 Uiso 0.49(3) 1 calc R U P A 2
Cl4A Cl 0.2035(6) 0.8196(5) 0.1003(4) 0.0659(17) Uani 0.260(3) 1 d D U P B 1
Cl5A Cl 0.0508(4) 0.6483(7) 0.0334(4) 0.066(2) Uani 0.260(3) 1 d D U P B 1
Cl6A Cl 0.2546(6) 0.5708(7) 0.0860(4) 0.0484(16) Uani 0.260(3) 1 d D U P B 1
C21A C 0.1751(5) 0.6907(6) 0.0481(4) 0.0409(7) Uani 0.260(3) 1 d D U P B 1
H21A H 0.183846 0.710323 0.002966 0.049 Uiso 0.260(3) 1 calc R U P B 1
Cl4B Cl 0.1407(5) 0.8287(3) 0.0727(3) 0.0790(14) Uani 0.226(3) 1 d D U P C 2
Cl5B Cl 0.0541(5) 0.5936(6) 0.0320(5) 0.0751(18) Uani 0.226(3) 1 d D U P C 2
Cl6B Cl 0.2654(4) 0.6176(6) 0.1003(4) 0.082(2) Uani 0.226(3) 1 d D U P C 2
C21B C 0.1588(5) 0.6852(5) 0.0429(4) 0.0409(7) Uani 0.226(3) 1 d D U P C 2
H21B H 0.169205 0.694621 -0.002600 0.049 Uiso 0.226(3) 1 calc R U P C 2
Cl4C Cl 0.2414(2) 0.8135(3) 0.11398(18) 0.0570(6) Uani 0.514(3) 1 d D U P D 3
Cl5C Cl 0.0546(2) 0.6977(3) 0.0438(2) 0.0769(9) Uani 0.514(3) 1 d D U P D 3
Cl6C Cl 0.2353(4) 0.5589(4) 0.0832(3) 0.0727(14) Uani 0.514(3) 1 d D U P D 3
C21C C 0.1825(3) 0.7007(4) 0.0550(3) 0.0409(7) Uani 0.514(3) 1 d D U P D 3
H21C H 0.191479 0.719311 0.009775 0.049 Uiso 0.514(3) 1 calc R U P D 3



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
S1 O3 1.4208(14) . ?
S1 O2 1.4236(14) . ?
S1 O1 1.5013(12) . ?
S1 C19 1.835(2) . ?
F1 B1 1.370(2) . ?
F2 C19 1.329(2) . ?
F3 C19 1.322(2) . ?
F4 C19 1.310(3) . ?
O1 B1 1.578(2) . ?
N1 C13 1.337(2) . ?
N1 C1 1.455(2) . ?
N1 B1 1.520(2) . ?
N2 C15 1.335(2) . ?
N2 C18 1.472(2) . ?
N2 B1 1.504(2) . ?
C1 C2 1.403(2) . ?
C1 C6 1.403(2) . ?
C2 C3 1.394(2) . ?
C2 C7 1.524(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.522(2) . ?
C7 C9 1.530(3) . ?
C7 C8 1.533(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.531(3) . ?
C10 C11 1.534(3) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.389(2) . ?
C13 C16 1.500(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.94(2) . ?
C15 C17 1.499(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C18 1.527(3) 3_655 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
Cl1A C20A 1.733(3) . ?
Cl2A C20A 1.746(3) . ?
Cl3A C20A 1.746(3) . ?
C20A H20A 1.0000 . ?
Cl1B C20B 1.733(3) . ?
Cl2B C20B 1.746(3) . ?
Cl3B C20B 1.746(3) . ?
C20B H20B 1.0000 . ?
Cl4A C21A 1.747(4) . ?
Cl5A C21A 1.745(4) . ?
Cl6A C21A 1.746(4) . ?
C21A H21A 1.0000 . ?
Cl4B C21B 1.747(4) . ?
Cl5B C21B 1.744(4) . ?
Cl6B C21B 1.746(4) . ?
C21B H21B 1.0000 . ?
Cl4C C21C 1.747(3) . ?
Cl5C C21C 1.747(3) . ?
Cl6C C21C 1.748(3) . ?
C21C H21C 1.0000 . ?

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
O3 S1 O2 119.19(9) . . ?
O3 S1 O1 109.58(8) . . ?
O2 S1 O1 113.34(8) . . ?
O3 S1 C19 105.33(9) . . ?
O2 S1 C19 105.60(10) . . ?
O1 S1 C19 101.90(9) . . ?
S1 O1 B1 134.70(10) . . ?
C13 N1 C1 119.99(13) . . ?
C13 N1 B1 119.94(13) . . ?
C1 N1 B1 119.87(13) . . ?
C15 N2 C18 121.73(14) . . ?
C15 N2 B1 120.01(13) . . ?
C18 N2 B1 118.23(13) . . ?
C2 C1 C6 122.49(15) . . ?
C2 C1 N1 118.06(14) . . ?
C6 C1 N1 119.44(14) . . ?
C3 C2 C1 117.87(15) . . ?
C3 C2 C7 119.55(15) . . ?
C1 C2 C7 122.57(15) . . ?
C4 C3 C2 120.79(16) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.27(16) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.44(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 117.14(16) . . ?
C5 C6 C10 120.12(15) . . ?
C1 C6 C10 122.73(15) . . ?
C2 C7 C9 110.86(15) . . ?
C2 C7 C8 111.71(15) . . ?
C9 C7 C8 110.06(15) . . ?
C2 C7 H7 108.0 . . ?
C9 C7 H7 108.0 . . ?
C8 C7 H7 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C12 112.42(15) . . ?
C6 C10 C11 110.06(16) . . ?
C12 C10 C11 109.96(16) . . ?
C6 C10 H10 108.1 . . ?
C12 C10 H10 108.1 . . ?
C11 C10 H10 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C14 119.94(15) . . ?
N1 C13 C16 119.99(15) . . ?
C14 C13 C16 119.93(15) . . ?
C13 C14 C15 121.06(15) . . ?
C13 C14 H14 119.4(12) . . ?
C15 C14 H14 118.3(12) . . ?
N2 C15 C14 119.96(15) . . ?
N2 C15 C17 120.48(15) . . ?
C14 C15 C17 119.51(15) . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C18 110.16(16) . 3_655 ?
N2 C18 H18A 109.6 . . ?
C18 C18 H18A 109.6 3_655 . ?
N2 C18 H18B 109.6 . . ?
C18 C18 H18B 109.6 3_655 . ?
H18A C18 H18B 108.1 . . ?
F4 C19 F3 108.97(18) . . ?
F4 C19 F2 108.7(2) . . ?
F3 C19 F2 108.53(18) . . ?
F4 C19 S1 110.84(15) . . ?
F3 C19 S1 108.85(16) . . ?
F2 C19 S1 110.89(14) . . ?
F1 B1 N2 113.03(14) . . ?
F1 B1 N1 112.86(14) . . ?
N2 B1 N1 110.23(13) . . ?
F1 B1 O1 105.77(13) . . ?
N2 B1 O1 109.87(13) . . ?
N1 B1 O1 104.63(12) . . ?
Cl1A C20A Cl3A 110.3(3) . . ?
Cl1A C20A Cl2A 110.6(3) . . ?
Cl3A C20A Cl2A 109.6(3) . . ?
Cl1A C20A H20A 108.8 . . ?
Cl3A C20A H20A 108.8 . . ?
Cl2A C20A H20A 108.8 . . ?
Cl1B C20B Cl3B 110.7(3) . . ?
Cl1B C20B Cl2B 109.8(3) . . ?
Cl3B C20B Cl2B 110.2(3) . . ?
Cl1B C20B H20B 108.7 . . ?
Cl3B C20B H20B 108.7 . . ?
Cl2B C20B H20B 108.7 . . ?
Cl5A C21A Cl6A 109.7(4) . . ?
Cl5A C21A Cl4A 109.9(4) . . ?
Cl6A C21A Cl4A 111.0(4) . . ?
Cl5A C21A H21A 108.7 . . ?
Cl6A C21A H21A 108.7 . . ?
Cl4A C21A H21A 108.7 . . ?
Cl5B C21B Cl6B 110.3(4) . . ?
Cl5B C21B Cl4B 110.7(4) . . ?
Cl6B C21B Cl4B 110.1(4) . . ?
Cl5B C21B H21B 108.6 . . ?
Cl6B C21B H21B 108.6 . . ?
Cl4B C21B H21B 108.6 . . ?
Cl5C C21C Cl4C 110.0(2) . . ?
Cl5C C21C Cl6C 109.7(3) . . ?
Cl4C C21C Cl6C 110.6(3) . . ?
Cl5C C21C H21C 108.8 . . ?
Cl4C C21C H21C 108.9 . . ?
Cl6C C21C H21C 108.8 . . ?

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
O3 S1 O1 B1 -163.93(15) . . . . ?
O2 S1 O1 B1 -28.11(18) . . . . ?
C19 S1 O1 B1 84.87(16) . . . . ?
C13 N1 C1 C2 -87.74(18) . . . . ?
B1 N1 C1 C2 87.10(18) . . . . ?
C13 N1 C1 C6 92.64(18) . . . . ?
B1 N1 C1 C6 -92.53(18) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
N1 C1 C2 C3 -179.61(14) . . . . ?
C6 C1 C2 C7 179.24(16) . . . . ?
N1 C1 C2 C7 -0.4(2) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C7 C2 C3 C4 -179.82(16) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C10 178.23(17) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
N1 C1 C6 C5 -179.95(15) . . . . ?
C2 C1 C6 C10 -178.10(16) . . . . ?
N1 C1 C6 C10 1.5(2) . . . . ?
C3 C2 C7 C9 65.6(2) . . . . ?
C1 C2 C7 C9 -113.58(18) . . . . ?
C3 C2 C7 C8 -57.5(2) . . . . ?
C1 C2 C7 C8 123.27(18) . . . . ?
C5 C6 C10 C12 58.0(2) . . . . ?
C1 C6 C10 C12 -123.54(18) . . . . ?
C5 C6 C10 C11 -65.0(2) . . . . ?
C1 C6 C10 C11 113.53(19) . . . . ?
C1 N1 C13 C14 167.74(14) . . . . ?
B1 N1 C13 C14 -7.1(2) . . . . ?
C1 N1 C13 C16 -7.9(2) . . . . ?
B1 N1 C13 C16 177.29(14) . . . . ?
N1 C13 C14 C15 -15.4(2) . . . . ?
C16 C13 C14 C15 160.23(16) . . . . ?
C18 N2 C15 C14 -170.36(15) . . . . ?
B1 N2 C15 C14 11.5(2) . . . . ?
C18 N2 C15 C17 7.1(2) . . . . ?
B1 N2 C15 C17 -171.10(15) . . . . ?
C13 C14 C15 N2 13.2(2) . . . . ?
C13 C14 C15 C17 -164.21(16) . . . . ?
C15 N2 C18 C18 90.0(2) . . . 3_655 ?
B1 N2 C18 C18 -91.8(2) . . . 3_655 ?
O3 S1 C19 F4 -61.64(17) . . . . ?
O2 S1 C19 F4 171.37(15) . . . . ?
O1 S1 C19 F4 52.74(17) . . . . ?
O3 S1 C19 F3 58.19(17) . . . . ?
O2 S1 C19 F3 -68.79(17) . . . . ?
O1 S1 C19 F3 172.57(15) . . . . ?
O3 S1 C19 F2 177.51(15) . . . . ?
O2 S1 C19 F2 50.52(18) . . . . ?
O1 S1 C19 F2 -68.11(17) . . . . ?
C15 N2 B1 F1 -157.77(14) . . . . ?
C18 N2 B1 F1 24.0(2) . . . . ?
C15 N2 B1 N1 -30.4(2) . . . . ?
C18 N2 B1 N1 151.34(13) . . . . ?
C15 N2 B1 O1 84.35(17) . . . . ?
C18 N2 B1 O1 -93.86(16) . . . . ?
C13 N1 B1 F1 155.65(14) . . . . ?
C1 N1 B1 F1 -19.2(2) . . . . ?
C13 N1 B1 N2 28.22(19) . . . . ?
C1 N1 B1 N2 -146.61(13) . . . . ?
C13 N1 B1 O1 -89.85(16) . . . . ?
C1 N1 B1 O1 95.32(15) . . . . ?
S1 O1 B1 F1 -88.19(17) . . . . ?
S1 O1 B1 N2 34.1(2) . . . . ?
S1 O1 B1 N1 152.42(12) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR RAH30                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_RAH18
_database_code_depnum_ccdc_archive 'CCDC 2346142'
loop_
_audit_author_name
_audit_author_address
'Marie Cordier'
;Univ Rennes, CNRS, ISCR UMR, Rennes
France
;
_audit_update_record             
;
2024-07-09 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 novembre 2023                                         #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C34 H40 B2 F4 N4'
_chemical_formula_sum            'C34 H40 B2 F4 N4'
_chemical_formula_weight         602.32
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9364(15)
_cell_length_b                   7.0652(6)
_cell_length_c                   13.0809(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.394(3)
_cell_angle_gamma                90
_cell_volume                     1605.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9911
_cell_measurement_theta_min      3.1126
_cell_measurement_theta_max      27.4587
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0567411
_diffrn_orient_matrix_UB_21      -0.0106751
_diffrn_orient_matrix_UB_31      -0.0538112
_diffrn_orient_matrix_UB_12      0.0959202
_diffrn_orient_matrix_UB_22      -0.0115609
_diffrn_orient_matrix_UB_32      0.1034362
_diffrn_orient_matrix_UB_13      0.0016714
_diffrn_orient_matrix_UB_23      -0.0569876
_diffrn_orient_matrix_UB_33      -0.0079193


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             636
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.981

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0239
_diffrn_reflns_av_r_equivalents  0.0378
_diffrn_reflns_number            19534
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.113
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3664
_reflns_number_gt                3326
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  
'CRYSCALC (T. Roisnel, local program, ver. 2023)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0543P)²+0.8488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3664
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1188
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.044

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.31077(5) -0.12885(12) 0.06215(8) 0.0357(2) Uani 1 1 d . . . . .
F2 F 0.38223(5) -0.08777(13) 0.22848(7) 0.0375(2) Uani 1 1 d . . . . .
N1 N 0.27095(6) 0.11465(14) 0.16691(8) 0.0179(2) Uani 1 1 d . . . . .
N2 N 0.38954(6) 0.15209(15) 0.09988(8) 0.0194(2) Uani 1 1 d . . . . .
C1 C 0.20510(7) 0.00547(17) 0.17787(10) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.20175(8) -0.06169(18) 0.27728(11) 0.0257(3) Uani 1 1 d . . . . .
C3 C 0.13725(9) -0.1670(2) 0.28388(13) 0.0335(3) Uani 1 1 d . . . . .
H3 H 0.133354 -0.210526 0.351060 0.040 Uiso 1 1 calc R U . . .
C4 C 0.07901(8) -0.2099(2) 0.19632(15) 0.0373(4) Uani 1 1 d . . . . .
C5 C 0.08365(8) -0.1383(2) 0.09906(14) 0.0353(3) Uani 1 1 d . . . . .
H5 H 0.043443 -0.165290 0.038330 0.042 Uiso 1 1 calc R U . . .
C6 C 0.14586(7) -0.02782(19) 0.08823(11) 0.0258(3) Uani 1 1 d . . . . .
C7 C 0.26480(10) -0.0233(2) 0.37497(11) 0.0384(4) Uani 1 1 d . . . . .
H7A H 0.250476 -0.076744 0.436558 0.058 Uiso 1 1 calc R U . . .
H7B H 0.272224 0.113598 0.384272 0.058 Uiso 1 1 calc R U . . .
H7C H 0.312735 -0.081876 0.367656 0.058 Uiso 1 1 calc R U . . .
C8 C 0.01272(10) -0.3361(3) 0.2057(2) 0.0576(6) Uani 1 1 d . . . . .
H8A H 0.027620 -0.469063 0.202698 0.086 Uiso 1 1 calc R U . . .
H8B H -0.032202 -0.309357 0.147466 0.086 Uiso 1 1 calc R U . . .
H8C H -0.000124 -0.311570 0.273077 0.086 Uiso 1 1 calc R U . . .
C9 C 0.14835(9) 0.0565(2) -0.01641(12) 0.0372(4) Uani 1 1 d . . . . .
H9A H 0.153823 0.194225 -0.009417 0.056 Uiso 1 1 calc R U . . .
H9B H 0.100581 0.026052 -0.068995 0.056 Uiso 1 1 calc R U . . .
H9C H 0.192259 0.004173 -0.039029 0.056 Uiso 1 1 calc R U . . .
C10 C 0.27065(7) 0.30247(17) 0.17969(9) 0.0194(2) Uani 1 1 d . . . . .
C11 C 0.32968(7) 0.41363(17) 0.16080(10) 0.0211(3) Uani 1 1 d . . . . .
H11 H 0.331423 0.544356 0.178232 0.025 Uiso 1 1 calc R U . . .
C12 C 0.38651(7) 0.33789(18) 0.11681(9) 0.0199(2) Uani 1 1 d . . . . .
C13 C 0.20464(8) 0.3967(2) 0.21101(12) 0.0300(3) Uani 1 1 d . . . . .
H13A H 0.156796 0.371167 0.157497 0.045 Uiso 1 1 calc R U . . .
H13B H 0.213563 0.533583 0.216691 0.045 Uiso 1 1 calc R U . . .
H13C H 0.200479 0.346890 0.279295 0.045 Uiso 1 1 calc R U . . .
C14 C 0.44180(8) 0.4697(2) 0.08395(12) 0.0286(3) Uani 1 1 d . . . . .
H14A H 0.494087 0.444727 0.126438 0.043 Uiso 1 1 calc R U . . .
H14B H 0.427712 0.600892 0.094779 0.043 Uiso 1 1 calc R U . . .
H14C H 0.439749 0.449767 0.009165 0.043 Uiso 1 1 calc R U . . .
C15 C 0.44621(7) 0.07607(18) 0.04894(10) 0.0207(3) Uani 1 1 d . . . . .
C16 C 0.52168(7) 0.0494(2) 0.10596(10) 0.0277(3) Uani 1 1 d . . . . .
H16 H 0.536658 0.082392 0.178604 0.033 Uiso 1 1 calc R U . . .
C17 C 0.42450(7) 0.0257(2) -0.05671(10) 0.0283(3) Uani 1 1 d . . . . .
H17 H 0.372666 0.042413 -0.095682 0.034 Uiso 1 1 calc R U . . .
B1 B 0.33861(8) 0.0065(2) 0.13957(12) 0.0222(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3923(17) . ?
F2 B1 1.3987(17) . ?
N1 C10 1.3377(16) . ?
N1 C1 1.4473(15) . ?
N1 B1 1.5491(16) . ?
N2 C12 1.3346(16) . ?
N2 C15 1.4499(14) . ?
N2 B1 1.5484(17) . ?
C1 C6 1.3929(18) . ?
C1 C2 1.3994(18) . ?
C2 C3 1.3959(19) . ?
C2 C7 1.506(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C8 1.515(2) . ?
C5 C6 1.3976(19) . ?
C5 H5 0.9500 . ?
C6 C9 1.504(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3890(17) . ?
C10 C13 1.5013(16) . ?
C11 C12 1.3957(16) . ?
C11 H11 0.9500 . ?
C12 C14 1.4993(17) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C17 1.3860(18) . ?
C15 C16 1.3866(17) . ?
C16 C17 1.3918(17) 3_655 ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C1 119.18(10) . . ?
C10 N1 B1 123.07(10) . . ?
C1 N1 B1 117.74(10) . . ?
C12 N2 C15 120.18(10) . . ?
C12 N2 B1 123.08(10) . . ?
C15 N2 B1 116.58(10) . . ?
C6 C1 C2 121.66(12) . . ?
C6 C1 N1 118.50(11) . . ?
C2 C1 N1 119.83(11) . . ?
C3 C2 C1 117.76(13) . . ?
C3 C2 C7 120.17(13) . . ?
C1 C2 C7 122.06(12) . . ?
C4 C3 C2 122.30(14) . . ?
C4 C3 H3 118.8 . . ?
C2 C3 H3 118.8 . . ?
C3 C4 C5 118.34(13) . . ?
C3 C4 C8 120.66(16) . . ?
C5 C4 C8 120.98(17) . . ?
C4 C5 C6 121.78(14) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 118.05(13) . . ?
C1 C6 C9 120.69(12) . . ?
C5 C6 C9 121.25(13) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 120.78(11) . . ?
N1 C10 C13 120.13(11) . . ?
C11 C10 C13 119.05(11) . . ?
C10 C11 C12 121.58(11) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N2 C12 C11 120.64(11) . . ?
N2 C12 C14 120.42(11) . . ?
C11 C12 C14 118.87(11) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C15 C16 119.75(11) . . ?
C17 C15 N2 119.88(11) . . ?
C16 C15 N2 120.35(11) . . ?
C15 C16 C17 119.97(12) . 3_655 ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 3_655 . ?
C15 C17 C16 120.28(12) . 3_655 ?
C15 C17 H17 119.9 . . ?
C16 C17 H17 119.9 3_655 . ?
F1 B1 F2 107.63(11) . . ?
F1 B1 N2 110.31(11) . . ?
F2 B1 N2 109.90(10) . . ?
F1 B1 N1 110.29(10) . . ?
F2 B1 N1 110.57(10) . . ?
N2 B1 N1 108.14(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
C10 N1 C1 C6 91.05(14) . . . . ?
B1 N1 C1 C6 -88.36(14) . . . . ?
C10 N1 C1 C2 -88.13(14) . . . . ?
B1 N1 C1 C2 92.46(14) . . . . ?
C6 C1 C2 C3 1.10(19) . . . . ?
N1 C1 C2 C3 -179.75(11) . . . . ?
C6 C1 C2 C7 -178.83(13) . . . . ?
N1 C1 C2 C7 0.33(19) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C7 C2 C3 C4 -178.29(13) . . . . ?
C2 C3 C4 C5 -2.8(2) . . . . ?
C2 C3 C4 C8 175.66(14) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C8 C4 C5 C6 -177.47(14) . . . . ?
C2 C1 C6 C5 -2.78(19) . . . . ?
N1 C1 C6 C5 178.05(11) . . . . ?
C2 C1 C6 C9 175.96(13) . . . . ?
N1 C1 C6 C9 -3.20(18) . . . . ?
C4 C5 C6 C1 1.7(2) . . . . ?
C4 C5 C6 C9 -177.02(14) . . . . ?
C1 N1 C10 C11 -174.35(11) . . . . ?
B1 N1 C10 C11 5.03(18) . . . . ?
C1 N1 C10 C13 3.41(17) . . . . ?
B1 N1 C10 C13 -177.20(12) . . . . ?
N1 C10 C11 C12 7.29(19) . . . . ?
C13 C10 C11 C12 -170.50(12) . . . . ?
C15 N2 C12 C11 176.67(11) . . . . ?
B1 N2 C12 C11 -7.97(18) . . . . ?
C15 N2 C12 C14 -0.33(18) . . . . ?
B1 N2 C12 C14 175.03(12) . . . . ?
C10 C11 C12 N2 -5.81(19) . . . . ?
C10 C11 C12 C14 171.23(12) . . . . ?
C12 N2 C15 C17 -101.92(15) . . . . ?
B1 N2 C15 C17 82.43(15) . . . . ?
C12 N2 C15 C16 79.56(16) . . . . ?
B1 N2 C15 C16 -96.09(15) . . . . ?
C17 C15 C16 C17 0.7(2) . . . 3_655 ?
N2 C15 C16 C17 179.27(13) . . . 3_655 ?
C16 C15 C17 C16 -0.7(2) . . . 3_655 ?
N2 C15 C17 C16 -179.28(13) . . . 3_655 ?
C12 N2 B1 F1 138.11(12) . . . . ?
C15 N2 B1 F1 -46.38(14) . . . . ?
C12 N2 B1 F2 -103.38(13) . . . . ?
C15 N2 B1 F2 72.14(14) . . . . ?
C12 N2 B1 N1 17.41(16) . . . . ?
C15 N2 B1 N1 -167.07(10) . . . . ?
C10 N1 B1 F1 -136.63(12) . . . . ?
C1 N1 B1 F1 42.76(15) . . . . ?
C10 N1 B1 F2 104.45(13) . . . . ?
C1 N1 B1 F2 -76.16(14) . . . . ?
C10 N1 B1 N2 -15.93(16) . . . . ?
C1 N1 B1 N2 163.47(10) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR RAH18                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_RAH13
_database_code_depnum_ccdc_archive 'CCDC 2346147'
loop_
_audit_author_name
_audit_author_address
'Marie Cordier'
;Univ Rennes, CNRS, ISCR UMR, Rennes
France
;
_audit_update_record             
;
2024-07-09 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 16 octobre 2023                                          #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C30 H40 B2 F4 N4'
_chemical_formula_sum            'C30 H40 B2 F4 N4'
_chemical_formula_weight         554.28
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   7.0540(10)
_cell_length_b                   16.785(2)
_cell_length_c                   12.4247(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.900(5)
_cell_angle_gamma                90
_cell_volume                     1460.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8981
_cell_measurement_theta_min      2.4267
_cell_measurement_theta_max      27.5089
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.1034291
_diffrn_orient_matrix_UB_21      -0.0584010
_diffrn_orient_matrix_UB_31      -0.0792660
_diffrn_orient_matrix_UB_12      -0.0383401
_diffrn_orient_matrix_UB_22      0.0411027
_diffrn_orient_matrix_UB_32      0.0197442
_diffrn_orient_matrix_UB_13      0.0128596
_diffrn_orient_matrix_UB_23      0.0440882
_diffrn_orient_matrix_UB_33      -0.0668098


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.460
_exptl_crystal_size_min          0.280
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             588
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.644
_exptl_absorpt_correction_T_max  0.975

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0402
_diffrn_reflns_av_r_equivalents  0.0519
_diffrn_reflns_number            15811
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.049
_diffrn_reflns_theta_max         27.533
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             3338
_reflns_number_gt                2915
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  
'CRYSCALC (T. Roisnel, local program, ver. 2023)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0628P)²+0.6195P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3338
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1287
_refine_ls_wR_factor_gt          0.1229
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.058

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.54503(12) 0.16453(5) -0.06527(7) 0.0290(2) Uani 1 1 d . . . . .
F2 F 0.81458(13) 0.12040(5) -0.12548(6) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.84719(15) 0.20258(6) 0.03538(9) 0.0195(2) Uani 1 1 d . . . . .
N2 N 0.72262(16) 0.06197(6) 0.03690(9) 0.0213(2) Uani 1 1 d . . . . .
C1 C 0.84797(18) 0.28184(7) -0.01044(10) 0.0189(3) Uani 1 1 d . . . . .
C2 C 0.98583(19) 0.30277(8) -0.07763(10) 0.0212(3) Uani 1 1 d . . . . .
C3 C 0.9808(2) 0.37948(8) -0.12108(11) 0.0250(3) Uani 1 1 d . . . . .
H3 H 1.073475 0.394146 -0.166941 0.030 Uiso 1 1 calc R U . . .
C4 C 0.8444(2) 0.43515(8) -0.09944(11) 0.0253(3) Uani 1 1 d . . . . .
C5 C 0.7106(2) 0.41236(8) -0.03204(11) 0.0254(3) Uani 1 1 d . . . . .
H5 H 0.616675 0.449793 -0.016355 0.030 Uiso 1 1 calc R U . . .
C6 C 0.70927(19) 0.33651(8) 0.01335(10) 0.0225(3) Uani 1 1 d . . . . .
C7 C 1.1383(2) 0.24530(9) -0.10253(13) 0.0300(3) Uani 1 1 d . . . . .
H7A H 1.084218 0.207378 -0.157880 0.045 Uiso 1 1 calc R U . . .
H7B H 1.186996 0.216332 -0.036467 0.045 Uiso 1 1 calc R U . . .
H7C H 1.242923 0.274732 -0.129463 0.045 Uiso 1 1 calc R U . . .
C8 C 0.8426(2) 0.51806(9) -0.14702(13) 0.0350(4) Uani 1 1 d . . . . .
H8A H 0.767023 0.518101 -0.218543 0.052 Uiso 1 1 calc R U . . .
H8B H 0.973733 0.534616 -0.154260 0.052 Uiso 1 1 calc R U . . .
H8C H 0.786010 0.555227 -0.099095 0.052 Uiso 1 1 calc R U . . .
C9 C 0.5648(2) 0.31558(9) 0.08835(13) 0.0326(3) Uani 1 1 d . . . . .
H9A H 0.625422 0.317412 0.163539 0.049 Uiso 1 1 calc R U . . .
H9B H 0.515663 0.261813 0.071664 0.049 Uiso 1 1 calc R U . . .
H9C H 0.459245 0.353849 0.078759 0.049 Uiso 1 1 calc R U . . .
C10 C 0.94192(19) 0.18881(8) 0.13361(10) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.9308(2) 0.11489(8) 0.18278(11) 0.0256(3) Uani 1 1 d . . . . .
H11 H 1.002248 0.106154 0.251556 0.031 Uiso 1 1 calc R U . . .
C12 C 0.81876(19) 0.05313(8) 0.13501(11) 0.0234(3) Uani 1 1 d . . . . .
C13 C 1.0594(2) 0.25360(9) 0.19230(12) 0.0300(3) Uani 1 1 d . . . . .
H13A H 1.149150 0.274955 0.145228 0.045 Uiso 1 1 calc R U . . .
H13B H 1.130600 0.231790 0.258333 0.045 Uiso 1 1 calc R U . . .
H13C H 0.975072 0.296338 0.211643 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8116(2) -0.02425(9) 0.19587(13) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.680629 -0.044801 0.186748 0.048 Uiso 1 1 calc R U . . .
H14B H 0.852956 -0.015193 0.273042 0.048 Uiso 1 1 calc R U . . .
H14C H 0.896606 -0.063080 0.167393 0.048 Uiso 1 1 calc R U . . .
C15 C 0.60225(19) -0.00231(8) -0.01507(11) 0.0240(3) Uani 1 1 d . . . . .
H15A H 0.658658 -0.054510 0.007915 0.029 Uiso 1 1 calc R U . . .
H15B H 0.599053 0.001696 -0.094759 0.029 Uiso 1 1 calc R U . . .
B1 B 0.7307(2) 0.13801(9) -0.03170(12) 0.0210(3) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.3986(17) . ?
F2 B1 1.4002(16) . ?
N1 C10 1.3392(17) . ?
N1 C1 1.4474(16) . ?
N1 B1 1.5427(17) . ?
N2 C12 1.3301(18) . ?
N2 C15 1.4732(17) . ?
N2 B1 1.5397(18) . ?
C1 C6 1.3987(18) . ?
C1 C2 1.4004(18) . ?
C2 C3 1.3949(19) . ?
C2 C7 1.5042(19) . ?
C3 C4 1.390(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 C8 1.5115(19) . ?
C5 C6 1.3928(19) . ?
C5 H5 0.9500 . ?
C6 C9 1.5026(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.3894(19) . ?
C10 C13 1.5020(19) . ?
C11 C12 1.392(2) . ?
C11 H11 0.9500 . ?
C12 C14 1.5068(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C15 1.535(3) 3_655 ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C1 119.47(11) . . ?
C10 N1 B1 123.11(11) . . ?
C1 N1 B1 117.40(10) . . ?
C12 N2 C15 121.57(11) . . ?
C12 N2 B1 123.44(11) . . ?
C15 N2 B1 114.97(10) . . ?
C6 C1 C2 120.99(12) . . ?
C6 C1 N1 118.96(11) . . ?
C2 C1 N1 120.05(11) . . ?
C3 C2 C1 118.35(12) . . ?
C3 C2 C7 119.87(12) . . ?
C1 C2 C7 121.77(12) . . ?
C4 C3 C2 122.12(12) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C5 C4 C3 117.89(12) . . ?
C5 C4 C8 121.00(13) . . ?
C3 C4 C8 121.11(13) . . ?
C4 C5 C6 122.27(13) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C5 C6 C1 118.38(12) . . ?
C5 C6 C9 120.19(12) . . ?
C1 C6 C9 121.41(12) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 120.42(12) . . ?
N1 C10 C13 120.22(12) . . ?
C11 C10 C13 119.36(12) . . ?
C10 C11 C12 122.46(12) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
N2 C12 C11 120.56(12) . . ?
N2 C12 C14 120.79(12) . . ?
C11 C12 C14 118.64(12) . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 C15 111.41(13) . 3_655 ?
N2 C15 H15A 109.3 . . ?
C15 C15 H15A 109.3 3_655 . ?
N2 C15 H15B 109.3 . . ?
C15 C15 H15B 109.3 3_655 . ?
H15A C15 H15B 108.0 . . ?
F1 B1 F2 107.05(11) . . ?
F1 B1 N2 109.47(11) . . ?
F2 B1 N2 109.46(11) . . ?
F1 B1 N1 110.88(11) . . ?
F2 B1 N1 110.31(11) . . ?
N2 B1 N1 109.63(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
C10 N1 C1 C6 -87.56(15) . . . . ?
B1 N1 C1 C6 90.85(14) . . . . ?
C10 N1 C1 C2 92.58(15) . . . . ?
B1 N1 C1 C2 -89.00(15) . . . . ?
C6 C1 C2 C3 -0.46(19) . . . . ?
N1 C1 C2 C3 179.39(11) . . . . ?
C6 C1 C2 C7 178.88(13) . . . . ?
N1 C1 C2 C7 -1.27(19) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C7 C2 C3 C4 -179.15(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C8 179.65(13) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C8 C4 C5 C6 -179.70(13) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
C4 C5 C6 C9 178.23(13) . . . . ?
C2 C1 C6 C5 0.41(19) . . . . ?
N1 C1 C6 C5 -179.44(11) . . . . ?
C2 C1 C6 C9 -177.90(13) . . . . ?
N1 C1 C6 C9 2.25(19) . . . . ?
C1 N1 C10 C11 174.91(12) . . . . ?
B1 N1 C10 C11 -3.42(19) . . . . ?
C1 N1 C10 C13 -4.32(18) . . . . ?
B1 N1 C10 C13 177.36(12) . . . . ?
N1 C10 C11 C12 -1.8(2) . . . . ?
C13 C10 C11 C12 177.44(13) . . . . ?
C15 N2 C12 C11 -179.63(12) . . . . ?
B1 N2 C12 C11 1.68(19) . . . . ?
C15 N2 C12 C14 1.47(19) . . . . ?
B1 N2 C12 C14 -177.22(12) . . . . ?
C10 C11 C12 N2 2.7(2) . . . . ?
C10 C11 C12 C14 -178.39(13) . . . . ?
C12 N2 C15 C15 88.67(18) . . . 3_655 ?
B1 N2 C15 C15 -92.54(16) . . . 3_655 ?
C12 N2 B1 F1 -127.71(13) . . . . ?
C15 N2 B1 F1 53.53(14) . . . . ?
C12 N2 B1 F2 115.24(13) . . . . ?
C15 N2 B1 F2 -63.52(14) . . . . ?
C12 N2 B1 N1 -5.87(17) . . . . ?
C15 N2 B1 N1 175.36(10) . . . . ?
C10 N1 B1 F1 127.72(13) . . . . ?
C1 N1 B1 F1 -50.63(15) . . . . ?
C10 N1 B1 F2 -113.86(13) . . . . ?
C1 N1 B1 F2 67.78(14) . . . . ?
C10 N1 B1 N2 6.74(17) . . . . ?
C1 N1 B1 N2 -171.62(10) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR RAH13                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_RED
_database_code_depnum_ccdc_archive 'CCDC 2353046'
loop_
_audit_author_name
_audit_author_address
'Dr. Dipak Kumar Roy'
;Indian Institute of Technology Indore
India
;
_audit_update_record             
;
2024-05-04 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_audit_creation_date             2024-05-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H54 B2 N4 O2, 2(C F3 O3 S)'
_chemical_formula_sum            'C38 H54 B2 F6 N4 O8 S2'
_chemical_formula_weight         894.59
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.627(3)
_cell_length_b                   15.411(5)
_cell_length_c                   16.562(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.019(11)
_cell_angle_gamma                90
_cell_volume                     2189.9(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8242
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8
_cell_measurement_theta_min      2.8
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9244
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             940
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1128
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28532
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.995
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         2.374
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Kappa Apex2 CCD'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2434
_reflns_number_total             3850
_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       'APEX2/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX2 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 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-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3850
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0984
_refine_ls_R_factor_gt           0.0496
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1116
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
1.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10)
1.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C5(H5A,H5B,H5C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
1.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
C1 C 1.1120(3) 0.11993(17) 0.57328(16) 0.0297(7) Uani 1 1 d . . . . .
H1A H 1.014978 0.099442 0.589708 0.045 Uiso 1 1 calc R U . . .
H1B H 1.192275 0.114248 0.617675 0.045 Uiso 1 1 calc R U . . .
H1C H 1.138992 0.086208 0.528067 0.045 Uiso 1 1 calc R U . . .
C2 C 1.0959(3) 0.21275(17) 0.54905(14) 0.0171(6) Uani 1 1 d . . . . .
C3 C 1.1975(3) 0.27443(17) 0.58337(14) 0.0191(6) Uani 1 1 d . . . . .
H3 H 1.275679 0.257018 0.622979 0.023 Uiso 1 1 calc R U . . .
C4 C 1.1889(3) 0.36092(17) 0.56190(15) 0.0187(6) Uani 1 1 d . . . . .
C5 C 1.3005(3) 0.42473(18) 0.60331(16) 0.0283(7) Uani 1 1 d . . . . .
H5A H 1.372352 0.443425 0.566339 0.042 Uiso 1 1 calc R U . . .
H5B H 1.356966 0.397900 0.649767 0.042 Uiso 1 1 calc R U . . .
H5C H 1.244050 0.473913 0.620463 0.042 Uiso 1 1 calc R U . . .
C6 C 0.8607(3) 0.17460(16) 0.46049(14) 0.0168(6) Uani 1 1 d . . . . .
C7 C 0.7347(3) 0.15905(16) 0.50508(15) 0.0187(6) Uani 1 1 d . . . . .
C8 C 0.6192(3) 0.10385(17) 0.47022(16) 0.0257(7) Uani 1 1 d . . . . .
H8 H 0.533823 0.091606 0.498216 0.031 Uiso 1 1 calc R U . . .
C9 C 0.6282(3) 0.06674(17) 0.39506(16) 0.0262(7) Uani 1 1 d . . . . .
H9 H 0.548265 0.030952 0.372484 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7547(3) 0.08254(17) 0.35359(16) 0.0238(7) Uani 1 1 d . . . . .
H10 H 0.760210 0.056096 0.303502 0.029 Uiso 1 1 calc R U . . .
C11 C 0.8751(3) 0.13715(16) 0.38452(15) 0.0188(6) Uani 1 1 d . . . . .
C12 C 0.9587(3) 0.1959(2) 0.25534(16) 0.0406(9) Uani 1 1 d . . . . .
H12A H 0.896178 0.155335 0.222166 0.061 Uiso 1 1 calc R U . . .
H12B H 1.048159 0.211774 0.228692 0.061 Uiso 1 1 calc R U . . .
H12C H 0.898245 0.246789 0.263712 0.061 Uiso 1 1 calc R U . . .
C13 C 1.0119(3) 0.15433(17) 0.33697(15) 0.0225(7) Uani 1 1 d . . . . .
H13 H 1.081043 0.195547 0.368116 0.027 Uiso 1 1 calc R U . . .
C14 C 1.1053(4) 0.07182(19) 0.32560(19) 0.0403(8) Uani 1 1 d . . . . .
H14A H 1.041726 0.031305 0.292916 0.060 Uiso 1 1 calc R U . . .
H14B H 1.137066 0.046413 0.377637 0.060 Uiso 1 1 calc R U . . .
H14C H 1.195862 0.085884 0.299102 0.060 Uiso 1 1 calc R U . . .
C15 C 0.6372(3) 0.29015(18) 0.57465(16) 0.0296(7) Uani 1 1 d . . . . .
H15A H 0.695458 0.327993 0.543060 0.044 Uiso 1 1 calc R U . . .
H15B H 0.628639 0.315880 0.626783 0.044 Uiso 1 1 calc R U . . .
H15C H 0.534924 0.281374 0.547022 0.044 Uiso 1 1 calc R U . . .
C16 C 0.7209(3) 0.20290(17) 0.58594(15) 0.0236(7) Uani 1 1 d . . . . .
H16 H 0.826897 0.214460 0.611024 0.028 Uiso 1 1 calc R U . . .
C17 C 0.6405(3) 0.14643(19) 0.64464(16) 0.0360(8) Uani 1 1 d . . . . .
H17A H 0.533092 0.138734 0.624258 0.054 Uiso 1 1 calc R U . . .
H17B H 0.646893 0.174120 0.696805 0.054 Uiso 1 1 calc R U . . .
H17C H 0.691004 0.090897 0.649813 0.054 Uiso 1 1 calc R U . . .
C18 C 1.0621(3) 0.47807(16) 0.47781(15) 0.0208(6) Uani 1 1 d . . . . .
H18A H 1.033194 0.481336 0.419691 0.025 Uiso 1 1 calc R U . . .
H18B H 1.160795 0.507832 0.490072 0.025 Uiso 1 1 calc R U . . .
C19 C 0.3526(4) 0.3942(2) 0.32820(19) 0.0416(9) Uani 1 1 d . . . . .
B1 B 0.9649(4) 0.3257(2) 0.46490(17) 0.0191(7) Uani 1 1 d . . . . .
F1 F 0.1977(2) 0.39951(15) 0.31042(11) 0.0710(7) Uani 1 1 d . . . . .
F2 F 0.4173(3) 0.43414(13) 0.26871(12) 0.0727(7) Uani 1 1 d . . . . .
F3 F 0.3878(2) 0.44157(12) 0.39539(12) 0.0591(6) Uani 1 1 d . . . . .
N1 N 0.9789(2) 0.23715(12) 0.49247(11) 0.0157(5) Uani 1 1 d . . . . .
N2 N 1.0788(2) 0.38637(13) 0.50287(12) 0.0168(5) Uani 1 1 d . . . . .
O1 O 0.5839(2) 0.29233(13) 0.35338(11) 0.0324(5) Uani 1 1 d . . . . .
O2 O 0.3446(2) 0.25658(13) 0.41139(11) 0.0386(6) Uani 1 1 d . . . . .
O3 O 0.3606(2) 0.24300(14) 0.26625(11) 0.0422(6) Uani 1 1 d . . . . .
O4 O 0.8563(2) 0.35747(11) 0.40882(10) 0.0248(5) Uani 1 1 d . . . . .
H4 H 0.786381 0.321687 0.399359 0.037 Uiso 1 1 calc R U . . .
S1 S 0.41716(8) 0.28307(5) 0.34144(4) 0.0268(2) 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.488(4) . ?
C2 C3 1.375(4) . ?
C2 N1 1.357(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 C5 1.492(3) . ?
C4 N2 1.348(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.397(3) . ?
C6 C11 1.402(3) . ?
C6 N1 1.462(3) . ?
C7 C8 1.389(3) . ?
C7 C16 1.516(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.371(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(3) . ?
C11 C13 1.509(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 C13 1.523(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.527(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C16 1.528(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.525(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C18 1.520(5) 3_766 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 N2 1.476(3) . ?
C19 F1 1.340(3) . ?
C19 F2 1.333(3) . ?
C19 F3 1.339(3) . ?
C19 S1 1.807(3) . ?
B1 N1 1.440(3) . ?
B1 N2 1.451(4) . ?
B1 O4 1.341(3) . ?
O1 S1 1.4384(19) . ?
O2 S1 1.4327(19) . ?
O3 S1 1.4293(19) . ?
O4 H4 0.8200 . ?

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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 121.1(2) . . ?
N1 C2 C1 119.6(2) . . ?
N1 C2 C3 119.3(2) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.2(2) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 120.2(2) . . ?
N2 C4 C3 118.9(2) . . ?
N2 C4 C5 120.9(2) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 123.4(2) . . ?
C7 C6 N1 118.3(2) . . ?
C11 C6 N1 118.2(2) . . ?
C6 C7 C16 121.8(2) . . ?
C8 C7 C6 116.7(2) . . ?
C8 C7 C16 121.4(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.1 . . ?
C9 C10 C11 121.7(3) . . ?
C11 C10 H10 119.1 . . ?
C6 C11 C13 123.0(2) . . ?
C10 C11 C6 116.5(2) . . ?
C10 C11 C13 120.6(2) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 H12C 109.5 . . ?
C11 C13 C12 111.0(2) . . ?
C11 C13 H13 107.7 . . ?
C11 C13 C14 111.7(2) . . ?
C12 C13 H13 107.7 . . ?
C12 C13 C14 110.8(2) . . ?
C14 C13 H13 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
C7 C16 C15 111.3(2) . . ?
C7 C16 H16 107.4 . . ?
C7 C16 C17 113.1(2) . . ?
C15 C16 H16 107.4 . . ?
C17 C16 C15 109.8(2) . . ?
C17 C16 H16 107.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C18 H18A 109.6 3_766 . ?
C18 C18 H18B 109.6 3_766 . ?
H18A C18 H18B 108.2 . . ?
N2 C18 C18 110.1(3) . 3_766 ?
N2 C18 H18A 109.6 . . ?
N2 C18 H18B 109.6 . . ?
F1 C19 S1 111.8(2) . . ?
F2 C19 F1 107.1(3) . . ?
F2 C19 F3 106.6(3) . . ?
F2 C19 S1 112.3(2) . . ?
F3 C19 F1 106.5(3) . . ?
F3 C19 S1 112.1(2) . . ?
N1 B1 N2 116.3(2) . . ?
O4 B1 N1 126.5(2) . . ?
O4 B1 N2 117.2(2) . . ?
C2 N1 C6 120.5(2) . . ?
C2 N1 B1 120.9(2) . . ?
B1 N1 C6 118.5(2) . . ?
C4 N2 C18 121.6(2) . . ?
C4 N2 B1 121.4(2) . . ?
B1 N2 C18 117.0(2) . . ?
B1 O4 H4 109.5 . . ?
O1 S1 C19 102.33(14) . . ?
O2 S1 C19 102.29(14) . . ?
O2 S1 O1 115.63(12) . . ?
O3 S1 C19 103.36(14) . . ?
O3 S1 O1 114.05(12) . . ?
O3 S1 O2 116.33(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3 O3 0.93 2.41 3.215(3) 144.9 4_666 yes
C3 H3 O3 0.93 2.41 3.215(3) 144.9 4_666 yes
O4 H4 O1 0.82 1.89 2.631(2) 150.4 . yes
O4 H4 O1 0.82 1.89 2.631(2) 150.4 . yes

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
C1 C2 C3 C4 178.9(2) . . . . ?
C1 C2 N1 C6 5.5(3) . . . . ?
C1 C2 N1 B1 -176.9(2) . . . . ?
C2 C3 C4 C5 178.4(2) . . . . ?
C2 C3 C4 N2 -1.9(4) . . . . ?
C3 C2 N1 C6 -174.3(2) . . . . ?
C3 C2 N1 B1 3.3(4) . . . . ?
C3 C4 N2 C18 179.2(2) . . . . ?
C3 C4 N2 B1 3.3(4) . . . . ?
C5 C4 N2 C18 -1.1(4) . . . . ?
C5 C4 N2 B1 -177.0(2) . . . . ?
C6 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C16 C15 88.3(3) . . . . ?
C6 C7 C16 C17 -147.5(2) . . . . ?
C6 C11 C13 C12 -119.2(3) . . . . ?
C6 C11 C13 C14 116.7(3) . . . . ?
C7 C6 C11 C10 0.5(4) . . . . ?
C7 C6 C11 C13 -179.9(2) . . . . ?
C7 C6 N1 C2 83.2(3) . . . . ?
C7 C6 N1 B1 -94.4(3) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
C8 C7 C16 C15 -89.2(3) . . . . ?
C8 C7 C16 C17 35.0(3) . . . . ?
C8 C9 C10 C11 -1.4(4) . . . . ?
C9 C10 C11 C6 0.4(4) . . . . ?
C9 C10 C11 C13 -179.1(2) . . . . ?
C10 C11 C13 C12 60.3(3) . . . . ?
C10 C11 C13 C14 -63.8(3) . . . . ?
C11 C6 C7 C8 -0.5(4) . . . . ?
C11 C6 C7 C16 -178.2(2) . . . . ?
C11 C6 N1 C2 -100.3(3) . . . . ?
C11 C6 N1 B1 82.0(3) . . . . ?
C16 C7 C8 C9 177.2(2) . . . . ?
C18 C18 N2 C4 -95.6(3) 3_766 . . . ?
C18 C18 N2 B1 80.5(3) 3_766 . . . ?
F1 C19 S1 O1 175.7(2) . . . . ?
F1 C19 S1 O2 -64.2(2) . . . . ?
F1 C19 S1 O3 57.0(2) . . . . ?
F2 C19 S1 O1 55.2(3) . . . . ?
F2 C19 S1 O2 175.3(2) . . . . ?
F2 C19 S1 O3 -63.5(3) . . . . ?
F3 C19 S1 O1 -64.8(2) . . . . ?
F3 C19 S1 O2 55.2(2) . . . . ?
F3 C19 S1 O3 176.5(2) . . . . ?
N1 C2 C3 C4 -1.4(4) . . . . ?
N1 C6 C7 C8 175.7(2) . . . . ?
N1 C6 C7 C16 -1.9(3) . . . . ?
N1 C6 C11 C10 -175.7(2) . . . . ?
N1 C6 C11 C13 3.9(4) . . . . ?
N1 B1 N2 C4 -1.4(4) . . . . ?
N1 B1 N2 C18 -177.5(2) . . . . ?
N2 B1 N1 C2 -2.0(4) . . . . ?
N2 B1 N1 C6 175.7(2) . . . . ?
O4 B1 N1 C2 179.1(3) . . . . ?
O4 B1 N1 C6 -3.3(4) . . . . ?
O4 B1 N2 C4 177.6(2) . . . . ?
O4 B1 N2 C18 1.5(4) . . . . ?

_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_red1
_database_code_depnum_ccdc_archive 'CCDC 2346141'
loop_
_audit_author_name
_audit_author_address
'Dr. Dipak Kumar Roy'
;Indian Institute of Technology Indore
India
;
_audit_update_record             
;
2024-04-06 deposited with the CCDC.	2024-08-09 downloaded from the CCDC.
;
_audit_creation_date             2023-03-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H52 B2 F4 N4'
_chemical_formula_sum            'C36 H52 B2 F4 N4'
_chemical_formula_weight         638.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H52 B2 F4 N4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6320(7)
_cell_length_b                   14.7782(7)
_cell_length_c                   10.9398(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.606(7)
_cell_angle_gamma                90
_cell_volume                     1771.52(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4815
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.0070
_cell_measurement_theta_min      3.5200
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19815
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.325
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  -6.00   1.00   18.00    --   17.86 -53.00  49.00   42
  2  ω     -3.00  87.00   1.00   18.00    --   17.86  53.00-166.00   90
  3  ω     14.00  39.00   1.00   18.00    --   17.86 -53.00  49.00   25
  4  ω    -19.00   6.00   1.00   18.00    --  -19.11  53.00-166.00   25
  5  ω     39.00  65.00   1.00   18.00    --   17.86 178.00  90.00   26
  6  ω    -19.00  60.00   1.00   18.00    --   17.86 -99.00  30.00   79
  7  ω    -10.00  88.00   1.00   18.00    --   17.86  77.00 -90.00   98
  8  ω      9.00  35.00   1.00   18.00    --   17.86  57.00  90.00   26
  9  ω    -18.00  57.00   1.00   18.00    --   17.86 -99.00-150.00   75
 10  ω     13.00  38.00   1.00   18.00    --   17.86 -99.00 -60.00   25
 11  ω    -23.00  11.00   1.00   18.00    --  -19.11 -77.00  30.00   34
 12  ω    -79.00 -31.00   1.00   18.00    --  -19.11 -57.00  30.00   48
 13  ω    -29.00  42.00   1.00   18.00    --  -19.11  77.00 120.00   71
 14  ω    -68.00 -43.00   1.00   18.00    --  -19.11 -53.00  49.00   25
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0182389000
_diffrn_orient_matrix_UB_12      -0.0128236000
_diffrn_orient_matrix_UB_13      -0.0532343000
_diffrn_orient_matrix_UB_21      0.0614068000
_diffrn_orient_matrix_UB_22      0.0106925000
_diffrn_orient_matrix_UB_23      0.0364343000
_diffrn_orient_matrix_UB_31      0.0093829000
_diffrn_orient_matrix_UB_32      -0.0450173000
_diffrn_orient_matrix_UB_33      0.0238252000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2097
_reflns_number_total             3116
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_collection       'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     214
_refine_ls_number_reflns         3116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      1.067
_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)+(0.0636P)²+0.4405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1629
_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:
 C14(H14), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C2(H2a,H2b,H2c), C6(H6a,H6b,H6c), C13(H13a,H13b,H13c), C15(H15a,H15b,H15c),
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.67883(17) 0.46068(10) 0.3401(2) 0.0908(7) Uani 1 1 d . . . . .
F2 F 0.74747(14) 0.55769(14) 0.50786(18) 0.0870(6) Uani 1 1 d . . . . .
N1 N 0.53934(17) 0.56746(13) 0.3728(2) 0.0459(5) Uani 1 1 d . . . . .
N2 N 0.70821(15) 0.61628(12) 0.29251(19) 0.0389(5) Uani 1 1 d . . . . .
C1 C 0.4818(2) 0.49606(18) 0.4269(2) 0.0541(7) Uani 1 1 d . . . . .
H1A H 0.5061 0.4372 0.4047 0.065 Uiso 1 1 calc R U . . .
H1B H 0.3938 0.5007 0.3885 0.065 Uiso 1 1 calc R U . . .
C2 C 0.3581(2) 0.6646(2) 0.3353(4) 0.0804(10) Uani 1 1 d . . . . .
H2A H 0.3018 0.6189 0.2886 0.121 Uiso 1 1 calc R U . . .
H2B H 0.3307 0.7228 0.2978 0.121 Uiso 1 1 calc R U . . .
H2C H 0.3624 0.6644 0.4245 0.121 Uiso 1 1 calc R U . . .
C3 C 0.4827(2) 0.64521(18) 0.3275(3) 0.0508(7) Uani 1 1 d . . . . .
C4 C 0.5365(2) 0.70784(16) 0.2703(3) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.4984 0.7635 0.2460 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6453(2) 0.69147(15) 0.2473(2) 0.0434(6) Uani 1 1 d . . . . .
C6 C 0.6889(3) 0.75713(17) 0.1682(3) 0.0615(7) Uani 1 1 d . . . . .
H6A H 0.7751 0.7496 0.1870 0.092 Uiso 1 1 calc R U . . .
H6B H 0.6725 0.8178 0.1892 0.092 Uiso 1 1 calc R U . . .
H6C H 0.6470 0.7461 0.0776 0.092 Uiso 1 1 calc R U . . .
C7 C 0.81899(19) 0.59563(14) 0.2639(2) 0.0367(5) Uani 1 1 d . . . . .
C8 C 0.9316(2) 0.62659(15) 0.3479(2) 0.0428(6) Uani 1 1 d . . . . .
C9 C 1.0359(2) 0.59972(17) 0.3217(3) 0.0530(7) Uani 1 1 d . . . . .
H9 H 1.1120 0.6191 0.3759 0.064 Uiso 1 1 calc R U . . .
C10 C 1.0286(2) 0.54548(18) 0.2183(3) 0.0566(7) Uani 1 1 d . . . . .
H10 H 1.0997 0.5272 0.2042 0.068 Uiso 1 1 calc R U . . .
C11 C 0.9169(2) 0.51765(17) 0.1346(3) 0.0500(6) Uani 1 1 d . . . . .
H11 H 0.9132 0.4823 0.0631 0.060 Uiso 1 1 calc R U . . .
C12 C 0.8097(2) 0.54175(14) 0.1557(2) 0.0399(6) Uani 1 1 d . . . . .
C13 C 0.6642(3) 0.5536(2) -0.0727(3) 0.0804(10) Uani 1 1 d . . . . .
H13A H 0.7276 0.5361 -0.1058 0.121 Uiso 1 1 calc R U . . .
H13B H 0.6631 0.6183 -0.0654 0.121 Uiso 1 1 calc R U . . .
H13C H 0.5868 0.5331 -0.1309 0.121 Uiso 1 1 calc R U . . .
C14 C 0.6880(2) 0.51127(17) 0.0601(3) 0.0520(7) Uani 1 1 d . . . . .
H14 H 0.6238 0.5321 0.0929 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6796(3) 0.4081(2) 0.0497(4) 0.0853(11) Uani 1 1 d . . . . .
H15A H 0.5994 0.3911 -0.0058 0.128 Uiso 1 1 calc R U . . .
H15B H 0.6950 0.3826 0.1343 0.128 Uiso 1 1 calc R U . . .
H15C H 0.7391 0.3860 0.0138 0.128 Uiso 1 1 calc R U . . .
C16 C 0.9961(3) 0.7809(2) 0.4417(4) 0.0941(11) Uani 1 1 d . . . . .
H16A H 0.9445 0.8068 0.3617 0.141 Uiso 1 1 calc R U . . .
H16B H 1.0770 0.7733 0.4384 0.141 Uiso 1 1 calc R U . . .
H16C H 0.9988 0.8204 0.5123 0.141 Uiso 1 1 calc R U . . .
C17 C 1.0241(3) 0.6468(3) 0.5887(3) 0.0895(11) Uani 1 1 d . . . . .
H17A H 0.9899 0.5899 0.6010 0.134 Uiso 1 1 calc R U . . .
H17B H 1.0278 0.6867 0.6591 0.134 Uiso 1 1 calc R U . . .
H17C H 1.1050 0.6374 0.5861 0.134 Uiso 1 1 calc R U . . .
C18 C 0.9451(2) 0.68865(17) 0.4621(3) 0.0540(7) Uani 1 1 d . . . . .
H18 H 0.8637 0.6985 0.4677 0.065 Uiso 1 1 calc R U . . .
B1 B 0.6707(3) 0.5486(2) 0.3802(3) 0.0501(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.385(3) . ?
F2 B1 1.389(4) . ?
N1 C1 1.475(3) . ?
N1 C3 1.334(3) . ?
N1 B1 1.528(3) . ?
N2 C5 1.331(3) . ?
N2 C7 1.457(3) . ?
N2 B1 1.547(3) . ?
C1 C1 1.516(5) 3_666 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.508(3) . ?
C3 C4 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C5 C6 1.497(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C8 1.400(3) . ?
C7 C12 1.401(3) . ?
C8 C9 1.394(3) . ?
C8 C18 1.515(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.378(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 C14 1.519(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C14 1.520(4) . ?
C14 H14 0.9800 . ?
C14 C15 1.529(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C16 C18 1.532(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C17 C18 1.513(4) . ?
C18 H18 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 N1 B1 115.3(2) . . ?
C3 N1 C1 122.1(2) . . ?
C3 N1 B1 122.5(2) . . ?
C5 N2 C7 120.72(18) . . ?
C5 N2 B1 122.40(19) . . ?
C7 N2 B1 116.86(18) . . ?
N1 C1 C1 111.4(2) . 3_666 ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
C1 C1 H1A 109.3 3_666 . ?
C1 C1 H1B 109.3 3_666 . ?
H1A C1 H1B 108.0 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
N1 C3 C2 120.5(2) . . ?
N1 C3 C4 120.2(2) . . ?
C4 C3 C2 119.3(3) . . ?
C3 C4 H4 118.5 . . ?
C3 C4 C5 123.0(2) . . ?
C5 C4 H4 118.5 . . ?
N2 C5 C4 119.9(2) . . ?
N2 C5 C6 120.3(2) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 N2 119.4(2) . . ?
C8 C7 C12 122.0(2) . . ?
C12 C7 N2 118.54(19) . . ?
C7 C8 C18 123.6(2) . . ?
C9 C8 C7 117.3(2) . . ?
C9 C8 C18 119.0(2) . . ?
C8 C9 H9 119.3 . . ?
C10 C9 C8 121.4(2) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.8(2) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 C14 122.7(2) . . ?
C11 C12 C7 117.9(2) . . ?
C11 C12 C14 119.4(2) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
C12 C14 C13 111.4(2) . . ?
C12 C14 H14 107.7 . . ?
C12 C14 C15 111.6(2) . . ?
C13 C14 H14 107.7 . . ?
C13 C14 C15 110.6(3) . . ?
C15 C14 H14 107.7 . . ?
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 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C16 H16A 109.5 . . ?
C18 C16 H16B 109.5 . . ?
C18 C16 H16C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
C8 C18 C16 110.9(2) . . ?
C8 C18 H18 107.9 . . ?
C16 C18 H18 107.9 . . ?
C17 C18 C8 111.7(2) . . ?
C17 C18 C16 110.5(2) . . ?
C17 C18 H18 107.9 . . ?
F1 B1 F2 108.7(2) . . ?
F1 B1 N1 109.2(2) . . ?
F1 B1 N2 110.3(2) . . ?
F2 B1 N1 109.3(2) . . ?
F2 B1 N2 109.9(2) . . ?
N1 B1 N2 109.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C3 C4 C5 5.2(4) . . . . ?
N2 C7 C8 C9 175.5(2) . . . . ?
N2 C7 C8 C18 -5.9(3) . . . . ?
N2 C7 C12 C11 -175.80(19) . . . . ?
N2 C7 C12 C14 5.8(3) . . . . ?
C1 N1 C3 C2 2.6(4) . . . . ?
C1 N1 C3 C4 -175.9(2) . . . . ?
C1 N1 B1 F1 45.7(3) . . . . ?
C1 N1 B1 F2 -73.0(3) . . . . ?
C1 N1 B1 N2 166.6(2) . . . . ?
C2 C3 C4 C5 -173.3(3) . . . . ?
C3 N1 C1 C1 -94.4(3) . . . 3_666 ?
C3 N1 B1 F1 -138.0(2) . . . . ?
C3 N1 B1 F2 103.3(3) . . . . ?
C3 N1 B1 N2 -17.1(3) . . . . ?
C3 C4 C5 N2 -6.7(4) . . . . ?
C3 C4 C5 C6 171.4(3) . . . . ?
C5 N2 C7 C8 89.8(3) . . . . ?
C5 N2 C7 C12 -93.0(3) . . . . ?
C5 N2 B1 F1 135.8(2) . . . . ?
C5 N2 B1 F2 -104.5(3) . . . . ?
C5 N2 B1 N1 15.6(3) . . . . ?
C7 N2 C5 C4 176.9(2) . . . . ?
C7 N2 C5 C6 -1.2(3) . . . . ?
C7 N2 B1 F1 -46.0(3) . . . . ?
C7 N2 B1 F2 73.7(3) . . . . ?
C7 N2 B1 N1 -166.20(19) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C18 C16 -114.3(3) . . . . ?
C7 C8 C18 C17 121.9(3) . . . . ?
C7 C12 C14 C13 113.7(3) . . . . ?
C7 C12 C14 C15 -122.1(3) . . . . ?
C8 C7 C12 C11 1.4(3) . . . . ?
C8 C7 C12 C14 -177.1(2) . . . . ?
C8 C9 C10 C11 1.7(4) . . . . ?
C9 C8 C18 C16 64.2(3) . . . . ?
C9 C8 C18 C17 -59.6(3) . . . . ?
C9 C10 C11 C12 -2.0(4) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C10 C11 C12 C14 178.9(2) . . . . ?
C11 C12 C14 C13 -64.7(3) . . . . ?
C11 C12 C14 C15 59.5(3) . . . . ?
C12 C7 C8 C9 -1.6(3) . . . . ?
C12 C7 C8 C18 176.9(2) . . . . ?
C18 C8 C9 C10 -178.5(2) . . . . ?
B1 N1 C1 C1 81.9(3) . . . 3_666 ?
B1 N1 C3 C2 -173.5(3) . . . . ?
B1 N1 C3 C4 8.1(4) . . . . ?
B1 N2 C5 C4 -5.0(4) . . . . ?
B1 N2 C5 C6 176.9(2) . . . . ?
B1 N2 C7 C8 -88.5(3) . . . . ?
B1 N2 C7 C12 88.8(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.839
_oxdiff_exptl_absorpt_empirical_full_min 0.422
