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

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

data_LP54FMI
_audit_block_doi                 10.5517/ccdc.csd.cc2g01wf
_database_code_depnum_ccdc_archive 'CCDC 2264174'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H37 Cl2 Ga N5, C24 H20 B'
_chemical_formula_sum            'C49 H57 B Cl2 Ga N5'
_chemical_formula_weight         867.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ga Ga 0.2307 1.6083 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

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

_cell_length_a                   9.3560(8)
_cell_length_b                   15.4776(13)
_cell_length_c                   16.0042(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.6450(14)
_cell_angle_gamma                90
_cell_volume                     2220.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    5398
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      27.40

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.406
_exptl_crystal_size_mid          0.278
_exptl_crystal_size_min          0.192
_exptl_absorpt_coefficient_mu    0.780
_shelx_estimated_absorpt_T_min   0.742
_shelx_estimated_absorpt_T_max   0.865
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7694
_exptl_absorpt_correction_T_max  0.8447
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14392
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.280
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             10122
_reflns_number_gt                7833
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.916
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.993

_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. 
;

_computing_data_collection       'Apex3 (2019.1) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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_abs_structure_details 
; 
 Flack x determined using 2894 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10122
_refine_ls_number_parameters     547
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0941
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Ga1 Ga 0.71013(5) 0.64670(3) 0.85161(3) 0.02891(14) Uani 1 1 d . . . . .
Cl1 Cl 0.87390(15) 0.58402(10) 0.95858(8) 0.0457(4) Uani 1 1 d . . . . .
Cl2 Cl 0.56734(14) 0.74850(7) 0.87618(8) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.9558(5) 0.8015(4) 0.8399(3) 0.0529(14) Uani 1 1 d D . . . .
N2 N 0.8656(4) 0.7320(3) 0.8136(3) 0.0382(11) Uani 1 1 d . . . . .
N3 N 0.6881(4) 0.6095(2) 0.7298(2) 0.0236(8) Uani 1 1 d . . . . .
N4 N 0.5510(4) 0.5460(2) 0.8326(2) 0.0262(9) Uani 1 1 d . . . . .
N5 N 0.4775(4) 0.5007(2) 0.8803(2) 0.0253(9) Uani 1 1 d . . . . .
C1 C 1.1971(7) 1.0304(4) 0.7015(5) 0.076(2) Uani 1 1 d . . . . .
H1A H 1.132646 1.071590 0.719987 0.113 Uiso 1 1 calc R U . . .
H1B H 1.207275 1.047726 0.644626 0.113 Uiso 1 1 calc R U . . .
H1C H 1.295717 1.029602 0.744511 0.113 Uiso 1 1 calc R U . . .
C2 C 1.2298(8) 0.8773(4) 0.6669(6) 0.075(2) Uani 1 1 d . . . . .
H2A H 1.327119 0.876549 0.711139 0.112 Uiso 1 1 calc R U . . .
H2B H 1.242434 0.895899 0.610942 0.112 Uiso 1 1 calc R U . . .
H2C H 1.186464 0.819191 0.660838 0.112 Uiso 1 1 calc R U . . .
C3 C 1.1274(7) 0.9392(4) 0.6944(5) 0.0545(17) Uani 1 1 d . . . . .
H3 H 1.030344 0.940588 0.647447 0.065 Uiso 1 1 calc R U . . .
C4 C 1.0961(7) 0.9148(4) 0.7784(5) 0.062(2) Uani 1 1 d . . . . .
H4A H 1.046092 0.964029 0.797980 0.075 Uiso 1 1 calc R U . . .
H4B H 1.192242 0.904937 0.823440 0.075 Uiso 1 1 calc R U . . .
C5 C 0.9998(6) 0.8351(4) 0.7724(4) 0.0497(17) Uani 1 1 d . . . . .
C6 C 0.9353(5) 0.7853(3) 0.6997(4) 0.0372(13) Uani 1 1 d . . . . .
H6 H 0.944221 0.792478 0.642450 0.045 Uiso 1 1 calc R U . . .
C7 C 0.8549(5) 0.7229(3) 0.7284(3) 0.0316(12) Uani 1 1 d . . . . .
C8 C 1.1623(6) 0.7867(4) 0.9746(4) 0.0524(16) Uani 1 1 d D . . . .
H8A H 1.208583 0.812125 1.032066 0.079 Uiso 0.59 1 calc R U P A 1
H8B H 1.131302 0.727300 0.981766 0.079 Uiso 0.59 1 calc R U P A 1
H8C H 1.234292 0.786346 0.940611 0.079 Uiso 0.59 1 calc R U P A 1
H8D H 1.190653 0.731254 0.954377 0.079 Uiso 0.41 1 calc R U P B 2
H8E H 1.211920 0.833783 0.952928 0.079 Uiso 0.41 1 calc R U P B 2
H8F H 1.192556 0.787636 1.038508 0.079 Uiso 0.41 1 calc R U P B 2
C9 C 1.0265(9) 0.8398(6) 0.9271(5) 0.032(2) Uani 0.59 1 d D U P C 1
H9 H 1.057897 0.900510 0.919984 0.039 Uiso 0.59 1 calc R U P C 1
C10 C 0.9138(11) 0.8399(7) 0.9778(7) 0.033(2) Uani 0.59 1 d D U P C 1
H10A H 0.958558 0.864988 1.035619 0.049 Uiso 0.59 1 calc R U P C 1
H10B H 0.826866 0.874259 0.946650 0.049 Uiso 0.59 1 calc R U P C 1
H10C H 0.882389 0.780440 0.984223 0.049 Uiso 0.59 1 calc R U P C 1
C9B C 0.9957(11) 0.7979(8) 0.9408(7) 0.032(2) Uani 0.41 1 d D U P C 2
H9B H 0.943791 0.748225 0.959417 0.039 Uiso 0.41 1 calc R U P C 2
C10B C 0.9426(18) 0.8823(8) 0.9693(11) 0.040(3) Uani 0.41 1 d D U P C 2
H10D H 0.833972 0.886351 0.945619 0.060 Uiso 0.41 1 calc R U P C 2
H10E H 0.970082 0.884475 1.033094 0.060 Uiso 0.41 1 calc R U P C 2
H10F H 0.989446 0.930622 0.947513 0.060 Uiso 0.41 1 calc R U P C 2
C11 C 0.7628(4) 0.6517(4) 0.6818(3) 0.0258(9) Uani 1 1 d . . . . .
C12 C 0.7547(5) 0.6253(3) 0.5984(3) 0.0265(11) Uani 1 1 d . . . . .
H12 H 0.805378 0.656163 0.564151 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6708(5) 0.5527(3) 0.5658(3) 0.0252(10) Uani 1 1 d . . . . .
H13 H 0.667248 0.531990 0.509428 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5925(5) 0.5104(3) 0.6141(3) 0.0240(10) Uani 1 1 d . . . . .
H14 H 0.532821 0.461539 0.590912 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6023(5) 0.5401(3) 0.6969(3) 0.0247(10) Uani 1 1 d . . . . .
C16 C 0.5285(5) 0.5034(3) 0.7572(3) 0.0239(10) Uani 1 1 d . . . . .
C17 C 0.4394(5) 0.4316(3) 0.7554(3) 0.0250(10) Uani 1 1 d . . . . .
H17 H 0.407035 0.391211 0.709100 0.030 Uiso 1 1 calc R U . . .
C18 C 0.4068(5) 0.4305(3) 0.8346(3) 0.0245(10) Uani 1 1 d . . . . .
C19 C 0.3137(5) 0.3686(3) 0.8680(3) 0.0275(11) Uani 1 1 d . . . . .
H19A H 0.210492 0.391219 0.853753 0.033 Uiso 1 1 calc R U . . .
H19B H 0.352990 0.365477 0.932261 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3096(5) 0.2774(3) 0.8304(3) 0.0328(12) Uani 1 1 d . . . . .
H20 H 0.282928 0.281768 0.765445 0.039 Uiso 1 1 calc R U . . .
C21 C 0.4599(6) 0.2333(3) 0.8628(4) 0.0419(14) Uani 1 1 d . . . . .
H21A H 0.535525 0.267944 0.846594 0.063 Uiso 1 1 calc R U . . .
H21B H 0.454521 0.175864 0.836282 0.063 Uiso 1 1 calc R U . . .
H21C H 0.486860 0.227572 0.926374 0.063 Uiso 1 1 calc R U . . .
C22 C 0.1893(7) 0.2248(4) 0.8544(4) 0.0525(16) Uani 1 1 d . . . . .
H22A H 0.187606 0.166051 0.831262 0.079 Uiso 1 1 calc R U . . .
H22B H 0.091914 0.252105 0.829390 0.079 Uiso 1 1 calc R U . . .
H22C H 0.211058 0.222350 0.918026 0.079 Uiso 1 1 calc R U . . .
C23 C 0.5501(7) 0.4822(4) 1.0414(3) 0.0455(14) Uani 1 1 d . . . . .
H23A H 0.501753 0.425506 1.036297 0.068 Uiso 1 1 calc R U . . .
H23B H 0.545824 0.510133 1.095555 0.068 Uiso 1 1 calc R U . . .
H23C H 0.654539 0.474936 1.042118 0.068 Uiso 1 1 calc R U . . .
C24 C 0.4702(6) 0.5378(3) 0.9644(3) 0.0339(12) Uani 1 1 d . . . . .
H24 H 0.525592 0.593888 0.971500 0.041 Uiso 1 1 calc R U . . .
C25 C 0.3100(6) 0.5599(3) 0.9603(4) 0.0450(14) Uani 1 1 d . . . . .
H25A H 0.263892 0.592072 0.906597 0.067 Uiso 1 1 calc R U . . .
H25B H 0.308900 0.595293 1.010848 0.067 Uiso 1 1 calc R U . . .
H25C H 0.253992 0.506467 0.960744 0.067 Uiso 1 1 calc R U . . .
B31 B 0.6804(5) 0.2047(3) 0.6086(3) 0.0197(10) Uani 1 1 d . . . . .
C31 C 0.5080(5) 0.2408(3) 0.5812(3) 0.0197(9) Uani 1 1 d . . . . .
C32 C 0.3949(5) 0.2089(3) 0.6142(3) 0.0221(10) Uani 1 1 d . . . . .
H32 H 0.416658 0.161154 0.653133 0.026 Uiso 1 1 calc R U . . .
C33 C 0.2523(5) 0.2439(3) 0.5926(3) 0.0242(10) Uani 1 1 d . . . . .
H33 H 0.179694 0.219899 0.616831 0.029 Uiso 1 1 calc R U . . .
C34 C 0.2147(5) 0.3135(3) 0.5359(3) 0.0250(10) Uani 1 1 d . . . . .
H34 H 0.117274 0.337680 0.521233 0.030 Uiso 1 1 calc R U . . .
C35 C 0.3227(5) 0.3469(3) 0.5014(3) 0.0262(10) Uani 1 1 d . . . . .
H35 H 0.299125 0.394337 0.462100 0.031 Uiso 1 1 calc R U . . .
C36 C 0.4644(5) 0.3119(3) 0.5234(3) 0.0234(10) Uani 1 1 d . . . . .
H36 H 0.536150 0.336595 0.498764 0.028 Uiso 1 1 calc R U . . .
C37 C 0.7836(4) 0.2880(3) 0.6559(3) 0.0197(9) Uani 1 1 d . . . . .
C38 C 0.7620(5) 0.3258(3) 0.7309(3) 0.0249(10) Uani 1 1 d . . . . .
H38 H 0.688168 0.302041 0.754444 0.030 Uiso 1 1 calc R U . . .
C39 C 0.8436(5) 0.3965(3) 0.7725(3) 0.0262(10) Uani 1 1 d . . . . .
H39 H 0.826749 0.419027 0.824070 0.031 Uiso 1 1 calc R U . . .
C40 C 0.9499(5) 0.4341(3) 0.7386(3) 0.0302(12) Uani 1 1 d . . . . .
H40 H 1.004596 0.483314 0.765753 0.036 Uiso 1 1 calc R U . . .
C41 C 0.9746(5) 0.3987(3) 0.6646(3) 0.0295(11) Uani 1 1 d . . . . .
H41 H 1.047652 0.423302 0.640963 0.035 Uiso 1 1 calc R U . . .
C42 C 0.8931(5) 0.3274(3) 0.6246(3) 0.0242(10) Uani 1 1 d . . . . .
H42 H 0.912283 0.304350 0.573825 0.029 Uiso 1 1 calc R U . . .
C43 C 0.6957(5) 0.1225(3) 0.6746(3) 0.0218(10) Uani 1 1 d . . . . .
C44 C 0.6279(5) 0.0436(3) 0.6402(3) 0.0277(11) Uani 1 1 d . . . . .
H44 H 0.581081 0.040045 0.579248 0.033 Uiso 1 1 calc R U . . .
C45 C 0.6261(5) -0.0290(3) 0.6908(4) 0.0327(12) Uani 1 1 d . . . . .
H45 H 0.577030 -0.080103 0.664626 0.039 Uiso 1 1 calc R U . . .
C46 C 0.6962(6) -0.0266(3) 0.7795(4) 0.0372(13) Uani 1 1 d . . . . .
H46 H 0.693239 -0.075189 0.815206 0.045 Uiso 1 1 calc R U . . .
C47 C 0.7704(6) 0.0476(3) 0.8151(3) 0.0351(12) Uani 1 1 d . . . . .
H47 H 0.822534 0.049101 0.875522 0.042 Uiso 1 1 calc R U . . .
C48 C 0.7701(5) 0.1204(3) 0.7639(3) 0.0274(11) Uani 1 1 d . . . . .
H48 H 0.822375 0.170475 0.790539 0.033 Uiso 1 1 calc R U . . .
C49 C 0.7316(5) 0.1720(3) 0.5237(3) 0.0222(10) Uani 1 1 d . . . . .
C50 C 0.6580(5) 0.1868(3) 0.4360(3) 0.0249(10) Uani 1 1 d . . . . .
H50 H 0.568277 0.219472 0.421904 0.030 Uiso 1 1 calc R U . . .
C51 C 0.7097(5) 0.1559(3) 0.3677(3) 0.0290(10) Uani 1 1 d . . . . .
H51 H 0.655898 0.167969 0.308910 0.035 Uiso 1 1 calc R U . . .
C52 C 0.8388(5) 0.1081(3) 0.3864(3) 0.0321(12) Uani 1 1 d . . . . .
H52 H 0.875563 0.087388 0.340586 0.039 Uiso 1 1 calc R U . . .
C53 C 0.9142(5) 0.0905(3) 0.4720(3) 0.0345(12) Uani 1 1 d . . . . .
H53 H 1.002579 0.056574 0.485364 0.041 Uiso 1 1 calc R U . . .
C54 C 0.8620(5) 0.1218(3) 0.5383(3) 0.0313(12) Uani 1 1 d . . . . .
H54 H 0.916573 0.108899 0.596812 0.038 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ga1 N3 1.986(4) . ?
Ga1 N4 2.116(4) . ?
Ga1 Cl1 2.1719(14) . ?
Ga1 Cl2 2.1733(13) . ?
Ga1 N2 2.176(4) . ?
N1 N2 1.358(6) . ?
N1 C5 1.364(8) . ?
N1 C9 1.486(8) . ?
N1 C9B 1.551(10) . ?
N2 C7 1.346(6) . ?
N3 C11 1.346(6) . ?
N3 C15 1.353(6) . ?
N4 C16 1.337(6) . ?
N4 N5 1.360(5) . ?
N5 C18 1.370(6) . ?
N5 C24 1.482(6) . ?
C1 C3 1.544(8) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.507(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.504(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.514(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.382(7) . ?
C6 C7 1.382(7) . ?
C6 H6 0.9500 . ?
C7 C11 1.464(7) . ?
C8 C9B 1.506(10) . ?
C8 C9 1.521(9) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8 H8D 0.9800 . ?
C8 H8E 0.9800 . ?
C8 H8F 0.9800 . ?
C9 C10 1.505(9) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C9B C10B 1.512(12) . ?
C9B H9B 1.0000 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11 C12 1.376(6) . ?
C12 C13 1.384(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(6) . ?
C13 H13 0.9500 . ?
C14 C15 1.381(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.455(6) . ?
C16 C17 1.385(6) . ?
C17 C18 1.387(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.492(6) . ?
C19 C20 1.531(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.515(7) . ?
C20 C22 1.524(7) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.513(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.520(7) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
B31 C43 1.633(6) . ?
B31 C31 1.644(6) . ?
B31 C49 1.645(6) . ?
B31 C37 1.658(6) . ?
C31 C32 1.400(6) . ?
C31 C36 1.422(6) . ?
C32 C33 1.388(6) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.383(6) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(6) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 C38 1.401(6) . ?
C37 C42 1.403(6) . ?
C38 C39 1.389(6) . ?
C38 H38 0.9500 . ?
C39 C40 1.390(7) . ?
C39 H39 0.9500 . ?
C40 C41 1.384(7) . ?
C40 H40 0.9500 . ?
C41 C42 1.389(6) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C48 1.399(6) . ?
C43 C44 1.413(6) . ?
C44 C45 1.387(6) . ?
C44 H44 0.9500 . ?
C45 C46 1.383(7) . ?
C45 H45 0.9500 . ?
C46 C47 1.377(7) . ?
C46 H46 0.9500 . ?
C47 C48 1.394(6) . ?
C47 H47 0.9500 . ?
C48 H48 0.9500 . ?
C49 C50 1.394(6) . ?
C49 C54 1.408(6) . ?
C50 C51 1.400(6) . ?
C50 H50 0.9500 . ?
C51 C52 1.375(7) . ?
C51 H51 0.9500 . ?
C52 C53 1.377(7) . ?
C52 H52 0.9500 . ?
C53 C54 1.378(6) . ?
C53 H53 0.9500 . ?
C54 H54 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
N3 Ga1 N4 76.96(15) . . ?
N3 Ga1 Cl1 119.72(11) . . ?
N4 Ga1 Cl1 95.33(11) . . ?
N3 Ga1 Cl2 119.43(11) . . ?
N4 Ga1 Cl2 96.69(10) . . ?
Cl1 Ga1 Cl2 120.84(5) . . ?
N3 Ga1 N2 77.96(15) . . ?
N4 Ga1 N2 154.91(15) . . ?
Cl1 Ga1 N2 96.55(13) . . ?
Cl2 Ga1 N2 96.05(12) . . ?
N2 N1 C5 111.0(4) . . ?
N2 N1 C9 132.6(6) . . ?
C5 N1 C9 115.9(6) . . ?
N2 N1 C9B 103.7(6) . . ?
C5 N1 C9B 143.2(6) . . ?
C7 N2 N1 104.8(4) . . ?
C7 N2 Ga1 111.0(3) . . ?
N1 N2 Ga1 143.2(3) . . ?
C11 N3 C15 120.6(4) . . ?
C11 N3 Ga1 119.6(3) . . ?
C15 N3 Ga1 119.7(3) . . ?
C16 N4 N5 106.2(4) . . ?
C16 N4 Ga1 114.5(3) . . ?
N5 N4 Ga1 138.3(3) . . ?
N4 N5 C18 110.7(4) . . ?
N4 N5 C24 118.2(4) . . ?
C18 N5 C24 130.6(4) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C2 113.8(6) . . ?
C4 C3 C1 110.5(5) . . ?
C2 C3 C1 108.2(5) . . ?
C4 C3 H3 108.1 . . ?
C2 C3 H3 108.1 . . ?
C1 C3 H3 108.1 . . ?
C3 C4 C5 114.3(5) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
N1 C5 C6 107.2(5) . . ?
N1 C5 C4 124.7(5) . . ?
C6 C5 C4 128.1(6) . . ?
C5 C6 C7 105.0(5) . . ?
C5 C6 H6 127.5 . . ?
C7 C6 H6 127.5 . . ?
N2 C7 C6 112.0(4) . . ?
N2 C7 C11 117.2(4) . . ?
C6 C7 C11 130.8(5) . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C9B C8 H8D 109.5 . . ?
C9B C8 H8E 109.5 . . ?
H8D C8 H8E 109.5 . . ?
C9B C8 H8F 109.5 . . ?
H8D C8 H8F 109.5 . . ?
H8E C8 H8F 109.5 . . ?
N1 C9 C10 108.3(7) . . ?
N1 C9 C8 109.7(6) . . ?
C10 C9 C8 110.1(7) . . ?
N1 C9 H9 109.5 . . ?
C10 C9 H9 109.5 . . ?
C8 C9 H9 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C9B C10B 112.8(9) . . ?
C8 C9B N1 107.1(7) . . ?
C10B C9B N1 106.3(10) . . ?
C8 C9B H9B 110.2 . . ?
C10B C9B H9B 110.2 . . ?
N1 C9B H9B 110.2 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
N3 C11 C12 121.1(4) . . ?
N3 C11 C7 113.6(4) . . ?
C12 C11 C7 125.3(4) . . ?
C11 C12 C13 118.3(4) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 118.7(4) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 120.5(4) . . ?
N3 C15 C16 113.1(4) . . ?
C14 C15 C16 126.4(4) . . ?
N4 C16 C17 110.7(4) . . ?
N4 C16 C15 115.1(4) . . ?
C17 C16 C15 134.2(4) . . ?
C16 C17 C18 106.2(4) . . ?
C16 C17 H17 126.9 . . ?
C18 C17 H17 126.9 . . ?
N5 C18 C17 106.2(4) . . ?
N5 C18 C19 124.1(4) . . ?
C17 C18 C19 129.7(4) . . ?
C18 C19 C20 113.8(4) . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C21 C20 C22 110.7(4) . . ?
C21 C20 C19 111.4(4) . . ?
C22 C20 C19 109.4(4) . . ?
C21 C20 H20 108.4 . . ?
C22 C20 H20 108.4 . . ?
C19 C20 H20 108.4 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N5 C24 C23 112.2(4) . . ?
N5 C24 C25 110.4(4) . . ?
C23 C24 C25 114.5(4) . . ?
N5 C24 H24 106.4 . . ?
C23 C24 H24 106.4 . . ?
C25 C24 H24 106.4 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C43 B31 C31 109.5(3) . . ?
C43 B31 C49 107.6(3) . . ?
C31 B31 C49 112.4(4) . . ?
C43 B31 C37 112.2(4) . . ?
C31 B31 C37 104.8(3) . . ?
C49 B31 C37 110.3(3) . . ?
C32 C31 C36 114.3(4) . . ?
C32 C31 B31 124.7(4) . . ?
C36 C31 B31 120.9(4) . . ?
C33 C32 C31 122.9(4) . . ?
C33 C32 H32 118.5 . . ?
C31 C32 H32 118.5 . . ?
C34 C33 C32 120.8(4) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 118.3(4) . . ?
C35 C34 H34 120.9 . . ?
C33 C34 H34 120.9 . . ?
C36 C35 C34 120.6(4) . . ?
C36 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C35 C36 C31 123.0(4) . . ?
C35 C36 H36 118.5 . . ?
C31 C36 H36 118.5 . . ?
C38 C37 C42 115.1(4) . . ?
C38 C37 B31 120.5(4) . . ?
C42 C37 B31 124.3(4) . . ?
C39 C38 C37 123.0(4) . . ?
C39 C38 H38 118.5 . . ?
C37 C38 H38 118.5 . . ?
C38 C39 C40 120.0(4) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C41 C40 C39 118.8(4) . . ?
C41 C40 H40 120.6 . . ?
C39 C40 H40 120.6 . . ?
C40 C41 C42 120.3(4) . . ?
C40 C41 H41 119.8 . . ?
C42 C41 H41 119.8 . . ?
C41 C42 C37 122.8(4) . . ?
C41 C42 H42 118.6 . . ?
C37 C42 H42 118.6 . . ?
C48 C43 C44 114.5(4) . . ?
C48 C43 B31 127.2(4) . . ?
C44 C43 B31 118.3(4) . . ?
C45 C44 C43 123.5(5) . . ?
C45 C44 H44 118.3 . . ?
C43 C44 H44 118.3 . . ?
C46 C45 C44 119.7(5) . . ?
C46 C45 H45 120.1 . . ?
C44 C45 H45 120.1 . . ?
C47 C46 C45 118.8(5) . . ?
C47 C46 H46 120.6 . . ?
C45 C46 H46 120.6 . . ?
C46 C47 C48 121.0(5) . . ?
C46 C47 H47 119.5 . . ?
C48 C47 H47 119.5 . . ?
C47 C48 C43 122.5(4) . . ?
C47 C48 H48 118.8 . . ?
C43 C48 H48 118.8 . . ?
C50 C49 C54 114.4(4) . . ?
C50 C49 B31 127.2(4) . . ?
C54 C49 B31 118.4(4) . . ?
C49 C50 C51 123.3(4) . . ?
C49 C50 H50 118.4 . . ?
C51 C50 H50 118.4 . . ?
C52 C51 C50 119.5(4) . . ?
C52 C51 H51 120.2 . . ?
C50 C51 H51 120.2 . . ?
C51 C52 C53 119.4(4) . . ?
C51 C52 H52 120.3 . . ?
C53 C52 H52 120.3 . . ?
C52 C53 C54 120.2(5) . . ?
C52 C53 H53 119.9 . . ?
C54 C53 H53 119.9 . . ?
C53 C54 C49 123.2(5) . . ?
C53 C54 H54 118.4 . . ?
C49 C54 H54 118.4 . . ?

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
C5 N1 N2 C7 0.2(6) . . . . ?
C9 N1 N2 C7 -171.7(6) . . . . ?
C9B N1 N2 C7 -167.4(5) . . . . ?
C5 N1 N2 Ga1 -165.9(5) . . . . ?
C9 N1 N2 Ga1 22.2(10) . . . . ?
C9B N1 N2 Ga1 26.5(8) . . . . ?
C16 N4 N5 C18 -1.0(5) . . . . ?
Ga1 N4 N5 C18 -168.4(3) . . . . ?
C16 N4 N5 C24 -174.0(4) . . . . ?
Ga1 N4 N5 C24 18.6(6) . . . . ?
C2 C3 C4 C5 -69.8(7) . . . . ?
C1 C3 C4 C5 168.2(5) . . . . ?
N2 N1 C5 C6 0.0(7) . . . . ?
C9 N1 C5 C6 173.5(5) . . . . ?
C9B N1 C5 C6 159.8(9) . . . . ?
N2 N1 C5 C4 177.6(5) . . . . ?
C9 N1 C5 C4 -8.9(9) . . . . ?
C9B N1 C5 C4 -22.7(13) . . . . ?
C3 C4 C5 N1 -179.3(6) . . . . ?
C3 C4 C5 C6 -2.3(9) . . . . ?
N1 C5 C6 C7 -0.3(6) . . . . ?
C4 C5 C6 C7 -177.8(6) . . . . ?
N1 N2 C7 C6 -0.4(6) . . . . ?
Ga1 N2 C7 C6 170.7(3) . . . . ?
N1 N2 C7 C11 -180.0(4) . . . . ?
Ga1 N2 C7 C11 -8.8(5) . . . . ?
C5 C6 C7 N2 0.5(6) . . . . ?
C5 C6 C7 C11 179.9(5) . . . . ?
N2 N1 C9 C10 -42.4(10) . . . . ?
C5 N1 C9 C10 145.9(7) . . . . ?
N2 N1 C9 C8 77.8(8) . . . . ?
C5 N1 C9 C8 -93.9(7) . . . . ?
N2 N1 C9B C8 118.1(7) . . . . ?
C5 N1 C9B C8 -42.5(14) . . . . ?
N2 N1 C9B C10B -121.1(9) . . . . ?
C5 N1 C9B C10B 78.3(13) . . . . ?
C15 N3 C11 C12 -0.4(6) . . . . ?
Ga1 N3 C11 C12 177.3(3) . . . . ?
C15 N3 C11 C7 -177.6(4) . . . . ?
Ga1 N3 C11 C7 0.1(5) . . . . ?
N2 C7 C11 N3 6.3(6) . . . . ?
C6 C7 C11 N3 -173.1(5) . . . . ?
N2 C7 C11 C12 -170.8(4) . . . . ?
C6 C7 C11 C12 9.8(8) . . . . ?
N3 C11 C12 C13 -1.7(6) . . . . ?
C7 C11 C12 C13 175.2(5) . . . . ?
C11 C12 C13 C14 2.7(6) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
C11 N3 C15 C14 1.4(6) . . . . ?
Ga1 N3 C15 C14 -176.3(3) . . . . ?
C11 N3 C15 C16 -179.2(4) . . . . ?
Ga1 N3 C15 C16 3.1(5) . . . . ?
C13 C14 C15 N3 -0.3(6) . . . . ?
C13 C14 C15 C16 -179.6(4) . . . . ?
N5 N4 C16 C17 0.8(5) . . . . ?
Ga1 N4 C16 C17 171.7(3) . . . . ?
N5 N4 C16 C15 -178.2(4) . . . . ?
Ga1 N4 C16 C15 -7.4(5) . . . . ?
N3 C15 C16 N4 3.1(6) . . . . ?
C14 C15 C16 N4 -177.5(4) . . . . ?
N3 C15 C16 C17 -175.6(5) . . . . ?
C14 C15 C16 C17 3.7(8) . . . . ?
N4 C16 C17 C18 -0.3(5) . . . . ?
C15 C16 C17 C18 178.5(5) . . . . ?
N4 N5 C18 C17 0.8(5) . . . . ?
C24 N5 C18 C17 172.7(4) . . . . ?
N4 N5 C18 C19 -178.7(4) . . . . ?
C24 N5 C18 C19 -6.8(7) . . . . ?
C16 C17 C18 N5 -0.3(5) . . . . ?
C16 C17 C18 C19 179.1(4) . . . . ?
N5 C18 C19 C20 -152.0(4) . . . . ?
C17 C18 C19 C20 28.7(7) . . . . ?
C18 C19 C20 C21 68.2(5) . . . . ?
C18 C19 C20 C22 -169.1(4) . . . . ?
N4 N5 C24 C23 -116.2(5) . . . . ?
C18 N5 C24 C23 72.4(6) . . . . ?
N4 N5 C24 C25 114.8(5) . . . . ?
C18 N5 C24 C25 -56.6(6) . . . . ?
C43 B31 C31 C32 3.7(6) . . . . ?
C49 B31 C31 C32 123.3(4) . . . . ?
C37 B31 C31 C32 -116.9(4) . . . . ?
C43 B31 C31 C36 -179.5(4) . . . . ?
C49 B31 C31 C36 -59.9(5) . . . . ?
C37 B31 C31 C36 59.9(5) . . . . ?
C36 C31 C32 C33 -0.2(6) . . . . ?
B31 C31 C32 C33 176.8(4) . . . . ?
C31 C32 C33 C34 0.1(7) . . . . ?
C32 C33 C34 C35 0.2(6) . . . . ?
C33 C34 C35 C36 -0.4(7) . . . . ?
C34 C35 C36 C31 0.4(7) . . . . ?
C32 C31 C36 C35 0.0(6) . . . . ?
B31 C31 C36 C35 -177.2(4) . . . . ?
C43 B31 C37 C38 -58.7(5) . . . . ?
C31 B31 C37 C38 60.1(5) . . . . ?
C49 B31 C37 C38 -178.7(4) . . . . ?
C43 B31 C37 C42 123.2(4) . . . . ?
C31 B31 C37 C42 -118.0(4) . . . . ?
C49 B31 C37 C42 3.2(6) . . . . ?
C42 C37 C38 C39 -0.8(6) . . . . ?
B31 C37 C38 C39 -179.0(4) . . . . ?
C37 C38 C39 C40 1.6(7) . . . . ?
C38 C39 C40 C41 -1.5(7) . . . . ?
C39 C40 C41 C42 0.7(7) . . . . ?
C40 C41 C42 C37 0.0(7) . . . . ?
C38 C37 C42 C41 0.0(6) . . . . ?
B31 C37 C42 C41 178.1(4) . . . . ?
C31 B31 C43 C48 -108.7(5) . . . . ?
C49 B31 C43 C48 128.8(4) . . . . ?
C37 B31 C43 C48 7.2(6) . . . . ?
C31 B31 C43 C44 71.3(5) . . . . ?
C49 B31 C43 C44 -51.1(5) . . . . ?
C37 B31 C43 C44 -172.7(4) . . . . ?
C48 C43 C44 C45 3.9(6) . . . . ?
B31 C43 C44 C45 -176.2(4) . . . . ?
C43 C44 C45 C46 -1.4(7) . . . . ?
C44 C45 C46 C47 -2.0(7) . . . . ?
C45 C46 C47 C48 2.7(8) . . . . ?
C46 C47 C48 C43 0.0(7) . . . . ?
C44 C43 C48 C47 -3.1(6) . . . . ?
B31 C43 C48 C47 177.0(4) . . . . ?
C43 B31 C49 C50 133.5(4) . . . . ?
C31 B31 C49 C50 12.8(6) . . . . ?
C37 B31 C49 C50 -103.7(5) . . . . ?
C43 B31 C49 C54 -45.0(5) . . . . ?
C31 B31 C49 C54 -165.7(4) . . . . ?
C37 B31 C49 C54 77.8(5) . . . . ?
C54 C49 C50 C51 -1.1(6) . . . . ?
B31 C49 C50 C51 -179.6(4) . . . . ?
C49 C50 C51 C52 0.4(7) . . . . ?
C50 C51 C52 C53 0.8(7) . . . . ?
C51 C52 C53 C54 -1.1(8) . . . . ?
C52 C53 C54 C49 0.3(8) . . . . ?
C50 C49 C54 C53 0.7(7) . . . . ?
B31 C49 C54 C53 179.4(4) . . . . ?

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
C9B^b H9B^b Cl1 1.00 2.62 3.540(12) 152.3 . yes
C10B^b H10F^b Cl1 0.98 2.90 3.591(15) 128.0 2_757 yes
C24 H24 Cl2 1.00 2.92 3.766(5) 142.5 . yes

_refine_diff_density_max         0.665
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.060

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF, Hexane'
####################################################################### 
# 
# 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_LP78FMI_SQ
_audit_block_doi                 10.5517/ccdc.csd.cc2g01xg
_database_code_depnum_ccdc_archive 'CCDC 2264175'
loop_
_audit_author_name
_audit_author_address
'James C. Fettinger'
;University of California, Davis
United States of America
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-07-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H40 N5, C F3 O3 S [+ solvent]'
_chemical_formula_sum            'C27 H40 F3 N5 O3 S'
_chemical_formula_weight         571.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5277(3)
_cell_length_b                   12.2580(3)
_cell_length_c                   14.2389(4)
_cell_angle_alpha                110.4846(8)
_cell_angle_beta                 91.5578(8)
_cell_angle_gamma                104.6039(9)
_cell_volume                     1652.15(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9782
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      77.42

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.149
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.552
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.143
_exptl_absorpt_coefficient_mu    1.295
_shelx_estimated_absorpt_T_min   0.535
_shelx_estimated_absorpt_T_max   0.837
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7672
_exptl_absorpt_process_details   'SADABS 2016/2 (Sheldrick, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Photon2 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11526
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0115
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.340
_diffrn_reflns_theta_max         68.590
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6081
_reflns_number_gt                5944
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 Structure factors included contributions from the .fab file. 
  
 _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. 
;

_computing_data_collection       'Apex3 (2019.11-0) (Bruker, 2019)'
_computing_cell_refinement       'SAINT (8.38a) (Bruker, 2017)'
_computing_data_reduction        'SAINT (8.38a) (Bruker, 2017)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;C1->C4 group disordered in a 0.88:12 fashion. Restraints used
to model minor portion same as major.

Squeeze used to remove heavily disordered solvent region.,SQUEEZE
;
_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+0.8887P] 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         6081
_refine_ls_number_parameters     398
_refine_ls_number_restraints     31
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1146
_refine_ls_wR_factor_gt          0.1142
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
N1 N 0.24181(13) 0.26915(14) 0.43489(11) 0.0391(3) Uani 1 1 d . . . . .
N2 N 0.32831(13) 0.30864(14) 0.51885(10) 0.0388(3) Uani 1 1 d . . . . .
N3 N 0.58156(13) 0.41817(13) 0.65799(9) 0.0331(3) Uani 1 1 d . . . . .
N4 N 0.63404(12) 0.39068(12) 0.85609(9) 0.0289(3) Uani 1 1 d . . . . .
N5 N 0.68560(12) 0.42419(11) 0.95301(9) 0.0263(3) Uani 1 1 d . . . . .
C1 C 0.1539(3) 0.0695(3) 0.0785(2) 0.0729(9) Uani 0.88 1 d D U P A 1
H1A H 0.202091 0.118877 0.042641 0.109 Uiso 0.88 1 calc R U P A 1
H1B H 0.066650 0.083432 0.087493 0.109 Uiso 0.88 1 calc R U P A 1
H1C H 0.143158 -0.016493 0.039070 0.109 Uiso 0.88 1 calc R U P A 1
C2 C 0.2315(3) 0.1045(2) 0.18155(17) 0.0582(7) Uani 0.88 1 d D U P A 1
H2 H 0.187064 0.048229 0.214947 0.070 Uiso 0.88 1 calc R U P A 1
C3 C 0.3734(3) 0.0934(2) 0.1667(2) 0.0620(7) Uani 0.88 1 d D U P A 1
H3A H 0.368913 0.012593 0.117692 0.093 Uiso 0.88 1 calc R U P A 1
H3B H 0.420306 0.105240 0.231447 0.093 Uiso 0.88 1 calc R U P A 1
H3C H 0.420766 0.155163 0.141527 0.093 Uiso 0.88 1 calc R U P A 1
C4 C 0.2341(2) 0.2347(2) 0.24703(15) 0.0407(6) Uani 0.88 1 d D U P A 1
H4A H 0.279973 0.290068 0.214314 0.049 Uiso 0.88 1 calc R U P A 1
H4B H 0.141967 0.240169 0.250144 0.049 Uiso 0.88 1 calc R U P A 1
C1B C 0.182(2) 0.115(2) 0.0690(12) 0.076(4) Uani 0.12 1 d D U P A 2
H1B1 H 0.231132 0.081586 0.013679 0.114 Uiso 0.12 1 calc R U P A 2
H1B2 H 0.103862 0.050781 0.068718 0.114 Uiso 0.12 1 calc R U P A 2
H1B3 H 0.153306 0.181016 0.059851 0.114 Uiso 0.12 1 calc R U P A 2
C2B C 0.2696(16) 0.1624(13) 0.1688(10) 0.060(2) Uani 0.12 1 d D U P A 2
H2B H 0.350220 0.225859 0.168010 0.071 Uiso 0.12 1 calc R U P A 2
C3B C 0.3126(19) 0.0632(14) 0.1962(12) 0.043(3) Uani 0.12 1 d D U P A 2
H3B1 H 0.368875 0.100984 0.261449 0.064 Uiso 0.12 1 calc R U P A 2
H3B2 H 0.233843 0.002961 0.200367 0.064 Uiso 0.12 1 calc R U P A 2
H3B3 H 0.362008 0.023222 0.143802 0.064 Uiso 0.12 1 calc R U P A 2
C4B C 0.1995(13) 0.2161(19) 0.2596(8) 0.043(2) Uani 0.12 1 d D U P A 2
H4B1 H 0.159300 0.276293 0.248908 0.051 Uiso 0.12 1 calc R U P A 2
H4B2 H 0.128434 0.151156 0.268097 0.051 Uiso 0.12 1 calc R U P A 2
C5 C 0.30156(16) 0.27639(17) 0.35272(12) 0.0390(4) Uani 1 1 d D . . . .
C6 C 0.43418(16) 0.32472(17) 0.38586(12) 0.0381(4) Uani 1 1 d . . . . .
H6 H 0.503181 0.341966 0.347125 0.046 Uiso 1 1 calc R U . . .
C7 C 0.44676(15) 0.34350(16) 0.48955(12) 0.0347(4) Uani 1 1 d . . . . .
C8 C 0.57300(16) 0.39056(16) 0.55558(11) 0.0354(4) Uani 1 1 d . . . . .
C9 C 0.68905(17) 0.4079(2) 0.51167(12) 0.0444(4) Uani 1 1 d . . . . .
H9 H 0.684342 0.388709 0.440756 0.053 Uiso 1 1 calc R U . . .
C10 C 0.81009(17) 0.4524(2) 0.56940(13) 0.0475(5) Uani 1 1 d . . . . .
H10 H 0.888769 0.468177 0.539384 0.057 Uiso 1 1 calc R U . . .
C11 C 0.81688(16) 0.47404(18) 0.67191(12) 0.0404(4) Uani 1 1 d . . . . .
H11 H 0.900510 0.502636 0.712141 0.048 Uiso 1 1 calc R U . . .
C12 C 0.70230(15) 0.45412(15) 0.71546(11) 0.0324(3) Uani 1 1 d . . . . .
C13 C 0.71367(14) 0.46937(14) 0.82282(11) 0.0282(3) Uani 1 1 d . . . . .
C14 C 0.81585(14) 0.55250(14) 0.89806(11) 0.0281(3) Uani 1 1 d . . . . .
H14 H 0.884338 0.616591 0.892672 0.034 Uiso 1 1 calc R U . . .
C15 C 0.79542(14) 0.52107(13) 0.98176(10) 0.0263(3) Uani 1 1 d . . . . .
C16 C 0.87426(15) 0.57310(14) 1.08442(11) 0.0306(3) Uani 1 1 d . . . . .
H16A H 0.929249 0.519604 1.087889 0.037 Uiso 1 1 calc R U . . .
H16B H 0.812561 0.573847 1.135740 0.037 Uiso 1 1 calc R U . . .
C17 C 0.96428(16) 0.70166(15) 1.11070(12) 0.0349(3) Uani 1 1 d . . . . .
H17 H 1.013077 0.703361 1.051718 0.042 Uiso 1 1 calc R U . . .
C18 C 1.06599(17) 0.73587(16) 1.20195(13) 0.0400(4) Uani 1 1 d . . . . .
H18A H 1.123189 0.818185 1.217363 0.060 Uiso 1 1 calc R U . . .
H18B H 1.119893 0.678731 1.186741 0.060 Uiso 1 1 calc R U . . .
H18C H 1.020224 0.732653 1.260350 0.060 Uiso 1 1 calc R U . . .
C19 C 0.8855(2) 0.79360(17) 1.13007(18) 0.0576(6) Uani 1 1 d . . . . .
H19A H 0.821869 0.771415 1.070383 0.086 Uiso 1 1 calc R U . . .
H19B H 0.945809 0.874298 1.143921 0.086 Uiso 1 1 calc R U . . .
H19C H 0.837917 0.794504 1.188422 0.086 Uiso 1 1 calc R U . . .
C20 C 0.0630(3) 0.0876(3) 0.4165(3) 0.0997(11) Uani 1 1 d . . . . .
H20A H 0.087743 0.046782 0.350120 0.150 Uiso 1 1 calc R U . . .
H20B H -0.032520 0.056908 0.416014 0.150 Uiso 1 1 calc R U . . .
H20C H 0.110505 0.071582 0.468217 0.150 Uiso 1 1 calc R U . . .
C21 C 0.09914(17) 0.2228(2) 0.44014(15) 0.0496(5) Uani 1 1 d . . . . .
H21 H 0.048163 0.236952 0.387316 0.059 Uiso 1 1 calc R U . . .
C22 C 0.0639(2) 0.2913(3) 0.54154(17) 0.0784(8) Uani 1 1 d . . . . .
H22A H 0.107171 0.273609 0.594111 0.118 Uiso 1 1 calc R U . . .
H22B H -0.032265 0.266462 0.541091 0.118 Uiso 1 1 calc R U . . .
H22C H 0.093820 0.378574 0.555449 0.118 Uiso 1 1 calc R U . . .
C23 C 0.45996(17) 0.4210(2) 0.71050(13) 0.0454(4) Uani 1 1 d . . . . .
H23A H 0.413570 0.338867 0.705772 0.068 Uiso 1 1 calc R U . . .
H23B H 0.401355 0.452000 0.678241 0.068 Uiso 1 1 calc R U . . .
H23C H 0.485616 0.474140 0.781768 0.068 Uiso 1 1 calc R U . . .
C24 C 0.64842(19) 0.22532(15) 0.96606(13) 0.0412(4) Uani 1 1 d . . . . .
H24A H 0.607811 0.185806 0.895416 0.062 Uiso 1 1 calc R U . . .
H24B H 0.608543 0.175852 1.004524 0.062 Uiso 1 1 calc R U . . .
H24C H 0.743723 0.233968 0.969343 0.062 Uiso 1 1 calc R U . . .
C25 C 0.62561(15) 0.34896(14) 1.01054(11) 0.0301(3) Uani 1 1 d . . . . .
H25 H 0.669139 0.388969 1.082094 0.036 Uiso 1 1 calc R U . . .
C26 C 0.47853(17) 0.33971(17) 1.00967(15) 0.0429(4) Uani 1 1 d . . . . .
H26A H 0.466764 0.421273 1.037963 0.064 Uiso 1 1 calc R U . . .
H26B H 0.439852 0.292929 1.050466 0.064 Uiso 1 1 calc R U . . .
H26C H 0.434348 0.298996 0.940022 0.064 Uiso 1 1 calc R U . . .
S31 S 0.82052(4) 0.31954(4) 0.24996(3) 0.03744(13) Uani 1 1 d . . . . .
C31 C 0.76657(19) 0.1575(2) 0.22560(17) 0.0542(5) Uani 1 1 d . . . . .
F31 F 0.68899(12) 0.09458(11) 0.13804(11) 0.0650(3) Uani 1 1 d . . . . .
F32 F 0.69893(14) 0.13716(16) 0.29872(13) 0.0875(5) Uani 1 1 d . . . . .
F33 F 0.86979(13) 0.11201(13) 0.22255(12) 0.0740(4) Uani 1 1 d . . . . .
O31 O 0.69795(12) 0.35175(13) 0.25044(9) 0.0481(3) Uani 1 1 d . . . . .
O32 O 0.90013(13) 0.36791(14) 0.34712(9) 0.0511(3) Uani 1 1 d . . . . .
O33 O 0.89260(11) 0.32663(12) 0.16709(8) 0.0416(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.3439(19) . ?
N1 C5 1.363(2) . ?
N1 C21 1.480(2) . ?
N2 C7 1.340(2) . ?
N3 C8 1.3716(19) . ?
N3 C12 1.374(2) . ?
N3 C23 1.5018(19) . ?
N4 C13 1.338(2) . ?
N4 N5 1.3483(16) . ?
N5 C15 1.3624(19) . ?
N5 C25 1.4777(18) . ?
C1 C2 1.523(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C4 1.533(4) . ?
C2 C3 1.548(4) . ?
C2 H2 1.0000 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 C5 1.500(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1B C2B 1.515(9) . ?
C1B H1B1 0.9800 . ?
C1B H1B2 0.9800 . ?
C1B H1B3 0.9800 . ?
C2B C4B 1.532(10) . ?
C2B C3B 1.561(10) . ?
C2B H2B 1.0000 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C4B C5 1.515(9) . ?
C4B H4B1 0.9900 . ?
C4B H4B2 0.9900 . ?
C5 C6 1.369(2) . ?
C6 C7 1.410(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.466(2) . ?
C8 C9 1.390(2) . ?
C9 C10 1.370(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.377(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.471(2) . ?
C13 C14 1.401(2) . ?
C14 C15 1.382(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.4990(19) . ?
C16 C17 1.529(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C19 1.517(2) . ?
C17 C18 1.525(2) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.513(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.505(3) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.509(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.523(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
S31 O33 1.4363(11) . ?
S31 O31 1.4411(12) . ?
S31 O32 1.4423(13) . ?
S31 C31 1.824(2) . ?
C31 F31 1.330(2) . ?
C31 F33 1.336(2) . ?
C31 F32 1.336(2) . ?

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
N2 N1 C5 112.83(13) . . ?
N2 N1 C21 119.12(13) . . ?
C5 N1 C21 128.05(14) . . ?
C7 N2 N1 104.64(12) . . ?
C8 N3 C12 120.77(13) . . ?
C8 N3 C23 120.25(13) . . ?
C12 N3 C23 118.72(12) . . ?
C13 N4 N5 104.23(12) . . ?
N4 N5 C15 112.95(12) . . ?
N4 N5 C25 118.14(12) . . ?
C15 N5 C25 128.71(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C1 C2 C4 109.1(2) . . ?
C1 C2 C3 108.9(2) . . ?
C4 C2 C3 110.98(17) . . ?
C1 C2 H2 109.3 . . ?
C4 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C5 C4 C2 113.67(19) . . ?
C5 C4 H4A 108.8 . . ?
C2 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C2 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C2B C1B H1B1 109.5 . . ?
C2B C1B H1B2 109.5 . . ?
H1B1 C1B H1B2 109.5 . . ?
C2B C1B H1B3 109.5 . . ?
H1B1 C1B H1B3 109.5 . . ?
H1B2 C1B H1B3 109.5 . . ?
C1B C2B C4B 112.8(12) . . ?
C1B C2B C3B 114.4(12) . . ?
C4B C2B C3B 101.6(11) . . ?
C1B C2B H2B 109.2 . . ?
C4B C2B H2B 109.2 . . ?
C3B C2B H2B 109.2 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
C5 C4B C2B 108.0(9) . . ?
C5 C4B H4B1 110.1 . . ?
C2B C4B H4B1 110.1 . . ?
C5 C4B H4B2 110.1 . . ?
C2B C4B H4B2 110.1 . . ?
H4B1 C4B H4B2 108.4 . . ?
N1 C5 C6 106.11(14) . . ?
N1 C5 C4 126.15(16) . . ?
C6 C5 C4 127.70(16) . . ?
N1 C5 C4B 109.2(7) . . ?
C6 C5 C4B 144.2(6) . . ?
C5 C6 C7 105.49(14) . . ?
C5 C6 H6 127.3 . . ?
C7 C6 H6 127.3 . . ?
N2 C7 C6 110.93(14) . . ?
N2 C7 C8 124.54(14) . . ?
C6 C7 C8 124.49(14) . . ?
N3 C8 C9 118.86(14) . . ?
N3 C8 C7 123.12(14) . . ?
C9 C8 C7 118.02(14) . . ?
C10 C9 C8 120.81(15) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.47(16) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C12 C11 C10 119.96(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
N3 C12 C11 119.83(14) . . ?
N3 C12 C13 121.87(13) . . ?
C11 C12 C13 118.29(14) . . ?
N4 C13 C14 111.81(13) . . ?
N4 C13 C12 121.56(14) . . ?
C14 C13 C12 126.00(14) . . ?
C15 C14 C13 105.07(13) . . ?
C15 C14 H14 127.5 . . ?
C13 C14 H14 127.5 . . ?
N5 C15 C14 105.93(12) . . ?
N5 C15 C16 123.50(13) . . ?
C14 C15 C16 130.53(14) . . ?
C15 C16 C17 113.69(12) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C19 C17 C18 110.37(14) . . ?
C19 C17 C16 111.65(14) . . ?
C18 C17 C16 110.59(13) . . ?
C19 C17 H17 108.0 . . ?
C18 C17 H17 108.0 . . ?
C16 C17 H17 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 C22 110.44(17) . . ?
N1 C21 C20 110.08(18) . . ?
C22 C21 C20 112.3(2) . . ?
N1 C21 H21 108.0 . . ?
C22 C21 H21 108.0 . . ?
C20 C21 H21 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 H23A 109.5 . . ?
N3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N5 C25 C24 109.81(12) . . ?
N5 C25 C26 109.65(12) . . ?
C24 C25 C26 111.32(14) . . ?
N5 C25 H25 108.7 . . ?
C24 C25 H25 108.7 . . ?
C26 C25 H25 108.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O33 S31 O31 115.12(7) . . ?
O33 S31 O32 115.00(7) . . ?
O31 S31 O32 114.83(8) . . ?
O33 S31 C31 103.75(9) . . ?
O31 S31 C31 103.26(9) . . ?
O32 S31 C31 102.43(9) . . ?
F31 C31 F33 107.23(19) . . ?
F31 C31 F32 107.79(16) . . ?
F33 C31 F32 107.77(16) . . ?
F31 C31 S31 112.30(13) . . ?
F33 C31 S31 111.20(14) . . ?
F32 C31 S31 110.37(17) . . ?

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
C5 N1 N2 C7 0.7(2) . . . . ?
C21 N1 N2 C7 179.82(16) . . . . ?
C13 N4 N5 C15 -0.27(15) . . . . ?
C13 N4 N5 C25 -175.62(12) . . . . ?
C1 C2 C4 C5 176.7(2) . . . . ?
C3 C2 C4 C5 -63.3(2) . . . . ?
C1B C2B C4B C5 -172.0(15) . . . . ?
C3B C2B C4B C5 65.0(16) . . . . ?
N2 N1 C5 C6 -0.7(2) . . . . ?
C21 N1 C5 C6 -179.73(18) . . . . ?
N2 N1 C5 C4 177.09(19) . . . . ?
C21 N1 C5 C4 -1.9(3) . . . . ?
N2 N1 C5 C4B 173.1(8) . . . . ?
C21 N1 C5 C4B -5.9(9) . . . . ?
C2 C4 C5 N1 -93.0(2) . . . . ?
C2 C4 C5 C6 84.3(3) . . . . ?
C2B C4B C5 N1 -149.1(11) . . . . ?
C2B C4B C5 C6 21(2) . . . . ?
N1 C5 C6 C7 0.4(2) . . . . ?
C4 C5 C6 C7 -177.4(2) . . . . ?
C4B C5 C6 C7 -169.5(14) . . . . ?
N1 N2 C7 C6 -0.44(19) . . . . ?
N1 N2 C7 C8 -178.29(16) . . . . ?
C5 C6 C7 N2 0.0(2) . . . . ?
C5 C6 C7 C8 177.86(17) . . . . ?
C12 N3 C8 C9 -4.6(3) . . . . ?
C23 N3 C8 C9 169.53(17) . . . . ?
C12 N3 C8 C7 175.49(15) . . . . ?
C23 N3 C8 C7 -10.4(3) . . . . ?
N2 C7 C8 N3 -8.5(3) . . . . ?
C6 C7 C8 N3 173.93(17) . . . . ?
N2 C7 C8 C9 171.59(18) . . . . ?
C6 C7 C8 C9 -6.0(3) . . . . ?
N3 C8 C9 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 179.59(18) . . . . ?
C8 C9 C10 C11 3.5(3) . . . . ?
C9 C10 C11 C12 -1.8(3) . . . . ?
C8 N3 C12 C11 6.3(2) . . . . ?
C23 N3 C12 C11 -167.93(17) . . . . ?
C8 N3 C12 C13 -172.14(15) . . . . ?
C23 N3 C12 C13 13.6(2) . . . . ?
C10 C11 C12 N3 -3.0(3) . . . . ?
C10 C11 C12 C13 175.46(17) . . . . ?
N5 N4 C13 C14 0.19(15) . . . . ?
N5 N4 C13 C12 171.61(12) . . . . ?
N3 C12 C13 N4 41.1(2) . . . . ?
C11 C12 C13 N4 -137.37(17) . . . . ?
N3 C12 C13 C14 -148.78(16) . . . . ?
C11 C12 C13 C14 32.8(2) . . . . ?
N4 C13 C14 C15 -0.05(16) . . . . ?
C12 C13 C14 C15 -171.01(14) . . . . ?
N4 N5 C15 C14 0.24(16) . . . . ?
C25 N5 C15 C14 174.99(13) . . . . ?
N4 N5 C15 C16 -177.64(12) . . . . ?
C25 N5 C15 C16 -2.9(2) . . . . ?
C13 C14 C15 N5 -0.11(15) . . . . ?
C13 C14 C15 C16 177.57(14) . . . . ?
N5 C15 C16 C17 -161.92(13) . . . . ?
C14 C15 C16 C17 20.8(2) . . . . ?
C15 C16 C17 C19 71.40(18) . . . . ?
C15 C16 C17 C18 -165.29(13) . . . . ?
N2 N1 C21 C22 34.1(3) . . . . ?
C5 N1 C21 C22 -147.0(2) . . . . ?
N2 N1 C21 C20 -90.4(2) . . . . ?
C5 N1 C21 C20 88.5(3) . . . . ?
N4 N5 C25 C24 66.03(17) . . . . ?
C15 N5 C25 C24 -108.49(17) . . . . ?
N4 N5 C25 C26 -56.58(17) . . . . ?
C15 N5 C25 C26 128.90(16) . . . . ?
O33 S31 C31 F31 -60.67(16) . . . . ?
O31 S31 C31 F31 59.78(16) . . . . ?
O32 S31 C31 F31 179.36(14) . . . . ?
O33 S31 C31 F33 59.49(16) . . . . ?
O31 S31 C31 F33 179.94(14) . . . . ?
O32 S31 C31 F33 -60.48(17) . . . . ?
O33 S31 C31 F32 179.04(13) . . . . ?
O31 S31 C31 F32 -60.51(15) . . . . ?
O32 S31 C31 F32 59.07(14) . . . . ?

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
C6 H6 O31 0.95 2.50 3.437(2) 168.1 . yes
C9 H9 O31 0.95 2.60 3.547(2) 173.7 . yes
C11 H11 O32 0.95 2.64 3.194(2) 117.4 2_766 yes
C11 H11 O33 0.95 2.66 3.537(2) 154.3 2_766 yes
C14 H14 O33 0.95 2.53 3.3616(19) 145.7 2_766 yes
C25 H25 O31 1.00 2.62 3.4659(19) 142.9 1_556 yes

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.040



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF, Hexane'
