# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cs2829
_database_code_depnum_ccdc_archive 'CCDC 2193672'
loop_
_audit_author_name
_audit_author_address
'Carla Slebodnick'
;Virginia Tech
United States of America
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2022-05-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
swethajos16@vt.edu
slebod@vt.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 B F N O4'
_chemical_formula_sum            'C17 H21 B F N O4'
_chemical_formula_weight         333.16
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H21 B F N O4'
_chemical_oxdiff_usercomment     'Swetha Jos/Santos (SJ-10-002-D1)'
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'
B B 0.0090 0.0039 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   15.79900(10)
_cell_length_b                   10.96110(10)
_cell_length_c                   19.70330(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3412.11(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23355
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      77.1050
_cell_measurement_theta_min      3.9940
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1408
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0841
-1 0 0 0.1333
1 0 0 0.1273
0 0 -1 0.0756
0 0 1 0.0916
-2 5 2 0.0570
-4 5 1 0.0560
0 1 1 0.0706
5 4 1 0.1072

_exptl_crystal_recrystallization_method 'crystals grown from DCM/hexanes'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -1.0000 0.0000 -0.0029 0.0087 0.1402
-1.0000 -0.0000 -0.0000 -0.0948 -0.0229 -0.0006
1.0000 0.0000 0.0000 0.0948 0.0229 0.0006
0.0000 -0.0000 -1.0000 0.0183 -0.0759 0.0051
-0.0000 0.0000 1.0000 -0.0183 0.0759 -0.0051
-2.0000 5.0000 2.0000 -0.2117 0.0626 -0.7124
-4.0000 5.0000 1.0000 -0.3830 -0.0591 -0.7084
-0.0000 1.0000 1.0000 -0.0154 0.0672 -0.1453
5.0000 4.0000 1.0000 0.4673 0.1557 -0.5631

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            31838
_diffrn_reflns_point_group_measured_fraction_full 0.950
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.489
_diffrn_reflns_theta_min         4.033
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    118.00 178.00   0.50    0.25    --  110.00  45.00  90.00  120
  2  ω    101.00 127.00   0.50    0.25    --  110.00  61.00   0.00   52
  3  ω     92.00 174.00   0.50    0.25    --  110.00  45.00 -30.00  164
  4  ω    150.00 178.00   0.50    0.25    --  110.00  61.00   0.00   56
  5  ω    111.00 142.00   0.50    0.25    --  110.00  30.00  60.00   62
  6  ω     95.00 121.00   0.50    0.25    --  110.00   5.00  16.00   52
  7  ω     56.00  82.00   0.50    0.25    --  110.00   5.00  16.00   52
  8  ω     95.00 177.00   0.50    0.25    --  110.00  45.00-120.00  164
  9  ω    -59.00  27.00   0.50    0.05    --  -45.04  57.00   0.00  172
 10  ω    -92.00 -51.00   0.50    0.25    --  -88.50 134.00-132.00   82
 11  ω   -118.00 -89.00   0.50    0.05    --  -45.04 -77.00-120.00   58
 12  ω    -95.00 -69.00   0.50    0.05    --  -45.04-144.00-102.00   52
 13  ω    -13.00  33.00   0.50    0.05    --   45.04  -5.00-160.00   92
 14  ω    -22.00  33.00   0.50    0.05    --   45.04 -38.00 -60.00  110
 15  ω     96.00 170.00   0.50    0.25    --  110.00 126.00 141.00  148
 16  ω     43.00  69.00   0.50    0.25    --  110.00 -61.00 120.00   52
 17  ω     39.00  91.00   0.50    0.25    --  110.00 -77.00 120.00  104
 18  ω     54.00  92.00   0.50    0.25    --  110.00 -77.00   0.00   76
 19  ω     45.00  95.00   0.50    0.25    --  110.00 -77.00-150.00  100
 20  ω     40.00  91.00   0.50    0.25    --  110.00 -77.00-120.00  102
 21  ω     40.00  69.00   0.50    0.25    --  110.00 -61.00-150.00   58
 22  ω     38.00  91.00   0.50    0.25    --  110.00 -77.00 -60.00  106
 23  ω     40.00  68.00   0.50    0.25    --  110.00 -61.00   0.00   56
 24  ω     43.00  74.00   0.50    0.25    --  110.00 -77.00  90.00   62
 25  ω     58.00  84.00   0.50    0.25    --  110.00-134.00 160.00   52
 26  ω     85.00 118.00   0.50    0.25    --  110.00-134.00 160.00   66
 27  ω     82.00 112.00   0.50    0.25    --  110.00-125.00 120.00   60
 28  ω     60.00 112.00   0.50    0.25    --  110.00-125.00  90.00  104
 29  ω     41.00  68.00   0.50    0.25    --  110.00-125.00  30.00   54
 30  ω     69.00 106.00   0.50    0.25    --  110.00 -94.00 120.00   74
 31  ω     41.00  77.00   0.50    0.25    --  110.00-125.00 120.00   72
 32  ω     78.00 112.00   0.50    0.25    --  110.00-125.00  30.00   68
 33  ω     49.00  75.00   0.50    0.25    --  110.00-125.00-180.00   52
 34  ω     87.00 112.00   0.50    0.25    --  110.00-125.00-180.00   50
 35  ω     48.00 104.00   0.50    0.25    --  110.00 -94.00-180.00  112
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Rigaku Oxford Diffraction XtaLAB Synergy, Dualflex, HyPix 6000-HE'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0948073000
_diffrn_orient_matrix_UB_12      0.0028950000
_diffrn_orient_matrix_UB_13      -0.0182799000
_diffrn_orient_matrix_UB_21      0.0228968000
_diffrn_orient_matrix_UB_22      -0.0086652000
_diffrn_orient_matrix_UB_23      0.0758516000
_diffrn_orient_matrix_UB_31      0.0005637000
_diffrn_orient_matrix_UB_32      -0.1402166000
_diffrn_orient_matrix_UB_33      -0.0050703000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.897
_reflns_Friedel_fraction_max     0.877
_reflns_number_gt                6618
_reflns_number_total             6806
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         6806
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.039
_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)+(0.0594P)²+0.4911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.86(12)
 0.14(12)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B), C33(H33A,H33B), C34(H34A,H34B)
3.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C25(H25), C27(H27), C28(H28),
 C30(H30), C31(H31)
3.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C20(H20A,
 H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
B1 B 0.70884(15) 0.8700(2) 0.36084(12) 0.0210(4) Uani 1 1 d . . . . .
F1 F 0.42514(8) 0.81025(13) 0.59772(7) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.77653(10) 0.87857(14) 0.31766(8) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.63941(10) 0.93410(14) 0.33947(8) 0.0255(3) Uani 1 1 d . . . . .
O3 O 0.86717(10) 0.50241(13) 0.54693(10) 0.0244(3) Uani 1 1 d . . . . .
O4 O 0.91422(10) 0.55962(14) 0.44398(9) 0.0263(3) Uani 1 1 d . . . . .
N1 N 0.79152(11) 0.63992(15) 0.49000(9) 0.0195(3) Uani 1 1 d . . . . .
C1 C 0.74516(15) 0.9336(2) 0.25528(11) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.66470(17) 1.00386(19) 0.27966(12) 0.0278(5) Uani 1 1 d . . . . .
C3 C 0.72488(18) 0.8288(2) 0.20722(13) 0.0345(5) Uani 1 1 d . . . . .
H3A H 0.775619 0.778755 0.200561 0.052 Uiso 1 1 calc R U . . .
H3B H 0.706259 0.861631 0.163438 0.052 Uiso 1 1 calc R U . . .
H3C H 0.679729 0.778509 0.226732 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8148(2) 1.0117(3) 0.22553(16) 0.0431(7) Uani 1 1 d . . . . .
H4A H 0.831659 1.073856 0.258631 0.065 Uiso 1 1 calc R U . . .
H4B H 0.794202 1.051601 0.184190 0.065 Uiso 1 1 calc R U . . .
H4C H 0.863634 0.960302 0.214483 0.065 Uiso 1 1 calc R U . . .
C5 C 0.59223(19) 1.0037(3) 0.22931(16) 0.0423(7) Uani 1 1 d . . . . .
H5A H 0.572500 0.919816 0.222354 0.063 Uiso 1 1 calc R U . . .
H5B H 0.611626 1.037566 0.185998 0.063 Uiso 1 1 calc R U . . .
H5C H 0.545675 1.053446 0.247009 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6844(3) 1.1322(2) 0.30481(17) 0.0535(9) Uani 1 1 d . . . . .
H6A H 0.634275 1.166304 0.327121 0.080 Uiso 1 1 calc R U . . .
H6B H 0.700234 1.183815 0.266254 0.080 Uiso 1 1 calc R U . . .
H6C H 0.731371 1.128910 0.337252 0.080 Uiso 1 1 calc R U . . .
C7 C 0.70855(13) 0.79227(17) 0.42640(10) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.77527(13) 0.71804(18) 0.43618(11) 0.0193(4) Uani 1 1 d . . . . .
H8 H 0.816979 0.719313 0.401457 0.023 Uiso 1 1 calc R U . . .
C9 C 0.63343(12) 0.79933(17) 0.47226(10) 0.0176(4) Uani 1 1 d . . . . .
C10 C 0.62727(13) 0.88808(18) 0.52276(12) 0.0218(4) Uani 1 1 d . . . . .
H10 H 0.671563 0.945848 0.528289 0.026 Uiso 1 1 calc R U . . .
C11 C 0.55685(14) 0.89278(19) 0.56512(11) 0.0232(4) Uani 1 1 d . . . . .
H11 H 0.552669 0.952826 0.599725 0.028 Uiso 1 1 calc R U . . .
C12 C 0.49304(13) 0.80793(19) 0.55565(11) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.49583(13) 0.72065(18) 0.50570(12) 0.0228(4) Uani 1 1 d . . . . .
H13 H 0.450772 0.664199 0.499936 0.027 Uiso 1 1 calc R U . . .
C14 C 0.56670(13) 0.71741(17) 0.46378(11) 0.0209(4) Uani 1 1 d . . . . .
H14 H 0.569689 0.658188 0.428657 0.025 Uiso 1 1 calc R U . . .
C15 C 0.86262(13) 0.56718(17) 0.48913(11) 0.0208(4) Uani 1 1 d . . . . .
C16 C 0.79625(14) 0.5309(2) 0.59068(12) 0.0253(4) Uani 1 1 d . . . . .
H16A H 0.816362 0.563916 0.634581 0.030 Uiso 1 1 calc R U . . .
H16B H 0.762042 0.456942 0.599532 0.030 Uiso 1 1 calc R U . . .
C17 C 0.74373(13) 0.62647(18) 0.55276(11) 0.0218(4) Uani 1 1 d . . . . .
H17A H 0.685541 0.596949 0.543934 0.026 Uiso 1 1 calc R U . . .
H17B H 0.741014 0.704248 0.578210 0.026 Uiso 1 1 calc R U . . .
B2 B 0.46661(15) 0.6403(2) 0.14081(12) 0.0198(4) Uani 1 1 d . . . . .
F2 F 0.18082(9) 0.68337(14) -0.09484(8) 0.0340(3) Uani 1 1 d . . . . .
O5 O 0.53229(9) 0.64015(14) 0.18634(7) 0.0221(3) Uani 1 1 d . . . . .
O6 O 0.39910(10) 0.56973(14) 0.16075(8) 0.0231(3) Uani 1 1 d . . . . .
O7 O 0.62130(9) 1.00241(13) -0.05110(9) 0.0219(3) Uani 1 1 d . . . . .
O8 O 0.67041(9) 0.94824(13) 0.05136(8) 0.0238(3) Uani 1 1 d . . . . .
N2 N 0.54773(11) 0.86404(15) 0.00710(9) 0.0190(3) Uani 1 1 d . . . . .
C18 C 0.49964(14) 0.58502(19) 0.24857(10) 0.0224(4) Uani 1 1 d . . . . .
C19 C 0.42619(15) 0.50271(19) 0.22104(11) 0.0235(5) Uani 1 1 d . . . . .
C20 C 0.46866(15) 0.6883(2) 0.29359(12) 0.0278(4) Uani 1 1 d . . . . .
H20A H 0.515432 0.744759 0.302587 0.042 Uiso 1 1 calc R U . . .
H20B H 0.447847 0.654787 0.336569 0.042 Uiso 1 1 calc R U . . .
H20C H 0.422726 0.731988 0.270640 0.042 Uiso 1 1 calc R U . . .
C21 C 0.57071(16) 0.5162(2) 0.28344(14) 0.0328(5) Uani 1 1 d . . . . .
H21A H 0.596803 0.459475 0.251196 0.049 Uiso 1 1 calc R U . . .
H21B H 0.547861 0.470462 0.322044 0.049 Uiso 1 1 calc R U . . .
H21C H 0.613363 0.574264 0.299599 0.049 Uiso 1 1 calc R U . . .
C22 C 0.35082(17) 0.4910(2) 0.26859(14) 0.0318(5) Uani 1 1 d . . . . .
H22A H 0.326706 0.571995 0.277067 0.048 Uiso 1 1 calc R U . . .
H22B H 0.369334 0.455027 0.311629 0.048 Uiso 1 1 calc R U . . .
H22C H 0.307853 0.438590 0.247730 0.048 Uiso 1 1 calc R U . . .
C23 C 0.45607(19) 0.3784(2) 0.19671(14) 0.0360(5) Uani 1 1 d . . . . .
H23A H 0.410954 0.339228 0.170428 0.054 Uiso 1 1 calc R U . . .
H23B H 0.470244 0.327396 0.235952 0.054 Uiso 1 1 calc R U . . .
H23C H 0.506296 0.388348 0.168044 0.054 Uiso 1 1 calc R U . . .
C24 C 0.46590(13) 0.71507(17) 0.07392(10) 0.0192(4) Uani 1 1 d . . . . .
C25 C 0.53239(13) 0.78867(17) 0.06218(11) 0.0190(4) Uani 1 1 d . . . . .
H25 H 0.574729 0.789030 0.096409 0.023 Uiso 1 1 calc R U . . .
C26 C 0.39017(13) 0.70400(17) 0.02888(10) 0.0177(4) Uani 1 1 d . . . . .
C27 C 0.38668(13) 0.61879(18) -0.02365(12) 0.0219(4) Uani 1 1 d . . . . .
H27 H 0.433180 0.565444 -0.030984 0.026 Uiso 1 1 calc R U . . .
C28 C 0.31579(14) 0.61107(19) -0.06546(12) 0.0248(4) Uani 1 1 d . . . . .
H28 H 0.313533 0.553443 -0.101424 0.030 Uiso 1 1 calc R U . . .
C29 C 0.24899(13) 0.68902(19) -0.05340(12) 0.0232(4) Uani 1 1 d . . . . .
C30 C 0.24870(14) 0.77214(18) -0.00108(12) 0.0249(4) Uani 1 1 d . . . . .
H30 H 0.201308 0.823642 0.006627 0.030 Uiso 1 1 calc R U . . .
C31 C 0.32002(13) 0.77835(17) 0.04016(11) 0.0212(4) Uani 1 1 d . . . . .
H31 H 0.320923 0.834562 0.076853 0.025 Uiso 1 1 calc R U . . .
C32 C 0.61832(12) 0.93882(17) 0.00704(11) 0.0192(4) Uani 1 1 d . . . . .
C33 C 0.50091(13) 0.87290(17) -0.05648(11) 0.0205(4) Uani 1 1 d . . . . .
H33A H 0.440781 0.893857 -0.048479 0.025 Uiso 1 1 calc R U . . .
H33B H 0.504158 0.796014 -0.082708 0.025 Uiso 1 1 calc R U . . .
C34 C 0.54789(14) 0.9769(2) -0.09253(12) 0.0243(4) Uani 1 1 d . . . . .
H34A H 0.565192 0.951649 -0.138740 0.029 Uiso 1 1 calc R U . . .
H34B H 0.511333 1.049951 -0.096130 0.029 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
B1 O1 1.370(3) . ?
B1 O2 1.369(3) . ?
B1 C7 1.548(3) . ?
F1 C12 1.356(2) . ?
O1 C1 1.456(3) . ?
O2 C2 1.461(3) . ?
O3 C15 1.344(3) . ?
O3 C16 1.448(3) . ?
O4 C15 1.210(3) . ?
N1 C8 1.387(3) . ?
N1 C15 1.378(3) . ?
N1 C17 1.456(3) . ?
C1 C2 1.562(3) . ?
C1 C3 1.523(3) . ?
C1 C4 1.512(3) . ?
C2 C5 1.515(4) . ?
C2 C6 1.523(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.346(3) . ?
C7 C9 1.494(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.395(3) . ?
C9 C14 1.395(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.384(3) . ?
C12 C13 1.373(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.392(3) . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
B2 O5 1.372(3) . ?
B2 O6 1.375(3) . ?
B2 C24 1.552(3) . ?
F2 C29 1.353(2) . ?
O5 C18 1.461(2) . ?
O6 C19 1.461(3) . ?
O7 C32 1.342(3) . ?
O7 C34 1.446(3) . ?
O8 C32 1.204(3) . ?
N2 C25 1.385(3) . ?
N2 C32 1.384(2) . ?
N2 C33 1.458(3) . ?
C18 C19 1.567(3) . ?
C18 C20 1.519(3) . ?
C18 C21 1.517(3) . ?
C19 C22 1.521(3) . ?
C19 C23 1.520(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.344(3) . ?
C24 C26 1.495(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.395(3) . ?
C26 C31 1.394(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.379(3) . ?
C29 C30 1.376(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(3) . ?
C31 H31 0.9500 . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.534(3) . ?
C34 H34A 0.9900 . ?
C34 H34B 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
O1 B1 C7 123.96(19) . . ?
O2 B1 O1 113.55(19) . . ?
O2 B1 C7 122.47(19) . . ?
B1 O1 C1 106.67(17) . . ?
B1 O2 C2 107.31(17) . . ?
C15 O3 C16 110.43(16) . . ?
C8 N1 C17 128.01(17) . . ?
C15 N1 C8 119.91(17) . . ?
C15 N1 C17 112.01(17) . . ?
O1 C1 C2 102.81(17) . . ?
O1 C1 C3 106.50(18) . . ?
O1 C1 C4 108.3(2) . . ?
C3 C1 C2 113.1(2) . . ?
C4 C1 C2 115.6(2) . . ?
C4 C1 C3 109.8(2) . . ?
O2 C2 C1 102.28(16) . . ?
O2 C2 C5 108.7(2) . . ?
O2 C2 C6 106.1(2) . . ?
C5 C2 C1 114.4(2) . . ?
C5 C2 C6 111.6(2) . . ?
C6 C2 C1 112.9(2) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 B1 116.75(18) . . ?
C8 C7 C9 124.56(18) . . ?
C9 C7 B1 118.61(18) . . ?
N1 C8 H8 115.6 . . ?
C7 C8 N1 128.89(19) . . ?
C7 C8 H8 115.6 . . ?
C10 C9 C7 121.54(18) . . ?
C14 C9 C7 119.65(18) . . ?
C14 C9 C10 118.80(18) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.62(19) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.8 . . ?
C12 C11 C10 118.46(19) . . ?
C12 C11 H11 120.8 . . ?
F1 C12 C11 118.76(19) . . ?
F1 C12 C13 118.47(19) . . ?
C13 C12 C11 122.8(2) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 117.96(19) . . ?
C14 C13 H13 121.0 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 C9 121.37(19) . . ?
C13 C14 H14 119.3 . . ?
O3 C15 N1 109.80(18) . . ?
O4 C15 O3 123.45(19) . . ?
O4 C15 N1 126.7(2) . . ?
O3 C16 H16A 110.5 . . ?
O3 C16 H16B 110.5 . . ?
O3 C16 C17 106.06(17) . . ?
H16A C16 H16B 108.7 . . ?
C17 C16 H16A 110.5 . . ?
C17 C16 H16B 110.5 . . ?
N1 C17 C16 101.69(16) . . ?
N1 C17 H17A 111.4 . . ?
N1 C17 H17B 111.4 . . ?
C16 C17 H17A 111.4 . . ?
C16 C17 H17B 111.4 . . ?
H17A C17 H17B 109.3 . . ?
O5 B2 O6 113.54(18) . . ?
O5 B2 C24 124.15(19) . . ?
O6 B2 C24 122.29(19) . . ?
B2 O5 C18 106.39(16) . . ?
B2 O6 C19 106.74(17) . . ?
C32 O7 C34 110.70(15) . . ?
C25 N2 C33 128.61(16) . . ?
C32 N2 C25 119.67(17) . . ?
C32 N2 C33 111.62(17) . . ?
O5 C18 C19 102.07(16) . . ?
O5 C18 C20 107.19(17) . . ?
O5 C18 C21 108.92(18) . . ?
C20 C18 C19 113.12(18) . . ?
C21 C18 C19 114.75(18) . . ?
C21 C18 C20 110.15(19) . . ?
O6 C19 C18 102.06(15) . . ?
O6 C19 C22 108.30(19) . . ?
O6 C19 C23 106.58(18) . . ?
C22 C19 C18 114.52(19) . . ?
C23 C19 C18 113.3(2) . . ?
C23 C19 C22 111.2(2) . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 B2 117.22(18) . . ?
C25 C24 C26 124.89(18) . . ?
C26 C24 B2 117.84(17) . . ?
N2 C25 H25 115.5 . . ?
C24 C25 N2 129.01(19) . . ?
C24 C25 H25 115.5 . . ?
C27 C26 C24 121.77(18) . . ?
C31 C26 C24 119.64(18) . . ?
C31 C26 C27 118.57(18) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.75(19) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 120.8 . . ?
C29 C28 C27 118.43(19) . . ?
C29 C28 H28 120.8 . . ?
F2 C29 C28 118.5(2) . . ?
F2 C29 C30 118.68(19) . . ?
C30 C29 C28 122.8(2) . . ?
C29 C30 H30 121.1 . . ?
C29 C30 C31 117.88(19) . . ?
C31 C30 H30 121.1 . . ?
C26 C31 H31 119.2 . . ?
C30 C31 C26 121.50(19) . . ?
C30 C31 H31 119.2 . . ?
O7 C32 N2 109.67(17) . . ?
O8 C32 O7 123.42(18) . . ?
O8 C32 N2 126.9(2) . . ?
N2 C33 H33A 111.4 . . ?
N2 C33 H33B 111.4 . . ?
N2 C33 C34 101.65(16) . . ?
H33A C33 H33B 109.3 . . ?
C34 C33 H33A 111.4 . . ?
C34 C33 H33B 111.4 . . ?
O7 C34 C33 105.68(17) . . ?
O7 C34 H34A 110.6 . . ?
O7 C34 H34B 110.6 . . ?
C33 C34 H34A 110.6 . . ?
C33 C34 H34B 110.6 . . ?
H34A C34 H34B 108.7 . . ?

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
B1 O1 C1 C2 23.6(2) . . . . ?
B1 O1 C1 C3 -95.6(2) . . . . ?
B1 O1 C1 C4 146.4(2) . . . . ?
B1 O2 C2 C1 20.5(2) . . . . ?
B1 O2 C2 C5 141.8(2) . . . . ?
B1 O2 C2 C6 -98.0(3) . . . . ?
B1 C7 C8 N1 179.50(19) . . . . ?
B1 C7 C9 C10 -87.0(2) . . . . ?
B1 C7 C9 C14 91.5(2) . . . . ?
F1 C12 C13 C14 -178.60(18) . . . . ?
O1 B1 O2 C2 -6.6(2) . . . . ?
O1 B1 C7 C8 -8.4(3) . . . . ?
O1 B1 C7 C9 174.69(19) . . . . ?
O1 C1 C2 O2 -26.6(2) . . . . ?
O1 C1 C2 C5 -143.9(2) . . . . ?
O1 C1 C2 C6 86.9(2) . . . . ?
O2 B1 O1 C1 -11.8(2) . . . . ?
O2 B1 C7 C8 169.40(19) . . . . ?
O2 B1 C7 C9 -7.5(3) . . . . ?
O3 C16 C17 N1 0.8(2) . . . . ?
C3 C1 C2 O2 87.8(2) . . . . ?
C3 C1 C2 C5 -29.5(3) . . . . ?
C3 C1 C2 C6 -158.6(2) . . . . ?
C4 C1 C2 O2 -144.4(2) . . . . ?
C4 C1 C2 C5 98.3(3) . . . . ?
C4 C1 C2 C6 -30.8(3) . . . . ?
C7 B1 O1 C1 166.13(19) . . . . ?
C7 B1 O2 C2 175.42(19) . . . . ?
C7 C9 C10 C11 -179.77(19) . . . . ?
C7 C9 C14 C13 179.66(19) . . . . ?
C8 N1 C15 O3 177.94(17) . . . . ?
C8 N1 C15 O4 -2.6(3) . . . . ?
C8 N1 C17 C16 -177.86(19) . . . . ?
C8 C7 C9 C10 96.3(2) . . . . ?
C8 C7 C9 C14 -85.1(3) . . . . ?
C9 C7 C8 N1 -3.8(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C9 C14 C13 -1.8(3) . . . . ?
C10 C11 C12 F1 178.52(19) . . . . ?
C10 C11 C12 C13 -0.9(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 C9 0.5(3) . . . . ?
C14 C9 C10 C11 1.7(3) . . . . ?
C15 O3 C16 C17 -0.4(2) . . . . ?
C15 N1 C8 C7 177.4(2) . . . . ?
C15 N1 C17 C16 -1.0(2) . . . . ?
C16 O3 C15 O4 -179.7(2) . . . . ?
C16 O3 C15 N1 -0.2(2) . . . . ?
C17 N1 C8 C7 -6.0(3) . . . . ?
C17 N1 C15 O3 0.8(2) . . . . ?
C17 N1 C15 O4 -179.7(2) . . . . ?
B2 O5 C18 C19 25.7(2) . . . . ?
B2 O5 C18 C20 -93.38(19) . . . . ?
B2 O5 C18 C21 147.46(19) . . . . ?
B2 O6 C19 C18 23.4(2) . . . . ?
B2 O6 C19 C22 144.53(18) . . . . ?
B2 O6 C19 C23 -95.7(2) . . . . ?
B2 C24 C25 N2 179.71(19) . . . . ?
B2 C24 C26 C27 -92.3(2) . . . . ?
B2 C24 C26 C31 86.1(2) . . . . ?
F2 C29 C30 C31 -178.73(18) . . . . ?
O5 B2 O6 C19 -8.2(2) . . . . ?
O5 B2 C24 C25 -3.5(3) . . . . ?
O5 B2 C24 C26 178.97(19) . . . . ?
O5 C18 C19 O6 -29.70(19) . . . . ?
O5 C18 C19 C22 -146.46(18) . . . . ?
O5 C18 C19 C23 84.5(2) . . . . ?
O6 B2 O5 C18 -12.4(2) . . . . ?
O6 B2 C24 C25 174.66(19) . . . . ?
O6 B2 C24 C26 -2.9(3) . . . . ?
N2 C33 C34 O7 7.9(2) . . . . ?
C20 C18 C19 O6 85.1(2) . . . . ?
C20 C18 C19 C22 -31.6(3) . . . . ?
C20 C18 C19 C23 -160.68(19) . . . . ?
C21 C18 C19 O6 -147.33(19) . . . . ?
C21 C18 C19 C22 95.9(2) . . . . ?
C21 C18 C19 C23 -33.1(3) . . . . ?
C24 B2 O5 C18 165.92(19) . . . . ?
C24 B2 O6 C19 173.51(19) . . . . ?
C24 C26 C27 C28 -179.28(19) . . . . ?
C24 C26 C31 C30 179.14(18) . . . . ?
C25 N2 C32 O7 179.28(16) . . . . ?
C25 N2 C32 O8 -0.9(3) . . . . ?
C25 N2 C33 C34 177.10(19) . . . . ?
C25 C24 C26 C27 90.3(3) . . . . ?
C25 C24 C26 C31 -91.2(3) . . . . ?
C26 C24 C25 N2 -2.9(3) . . . . ?
C26 C27 C28 C29 -0.4(3) . . . . ?
C27 C26 C31 C30 -2.3(3) . . . . ?
C27 C28 C29 F2 178.64(19) . . . . ?
C27 C28 C29 C30 -1.4(3) . . . . ?
C28 C29 C30 C31 1.3(3) . . . . ?
C29 C30 C31 C26 0.6(3) . . . . ?
C31 C26 C27 C28 2.2(3) . . . . ?
C32 O7 C34 C33 -7.1(2) . . . . ?
C32 N2 C25 C24 175.9(2) . . . . ?
C32 N2 C33 C34 -6.6(2) . . . . ?
C33 N2 C25 C24 -8.0(3) . . . . ?
C33 N2 C32 O7 2.6(2) . . . . ?
C33 N2 C32 O8 -177.6(2) . . . . ?
C34 O7 C32 O8 -176.74(19) . . . . ?
C34 O7 C32 N2 3.1(2) . . . . ?

_olex2_date_sample_data_collection 2022-04-21
_olex2_date_sample_submission    2022-04-18
_olex2_exptl_crystal_mounting_method 
'mounted on a nylon loop with perflourether oil'
_olex2_submission_original_sample_id SJ-10-002
_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 1.831
_oxdiff_exptl_absorpt_empirical_full_min 0.636
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.86(12)
2 0.14(12)

####################################################################### 
# 
# 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_cs2733
_database_code_depnum_ccdc_archive 'CCDC 2193673'
loop_
_audit_author_name
_audit_author_address
'Carla Slebodnick'
;Virginia Tech
United States of America
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2021-09-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
swethajos16@vt.edu
slebod@vt.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H22 B N O4'
_chemical_formula_sum            'C17 H22 B N O4'
_chemical_formula_weight         315.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H22 B N O4'
_chemical_oxdiff_usercomment     'Swetha Jos / Santos (SJ-10-001)'
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'
B B 0.0090 0.0039 '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'

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

_cell_length_a                   11.64540(10)
_cell_length_b                   10.87300(10)
_cell_length_c                   13.34130(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.9620(10)
_cell_angle_gamma                90
_cell_volume                     1652.60(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18218
_cell_measurement_temperature    100.00(11)
_cell_measurement_theta_max      77.2770
_cell_measurement_theta_min      4.5430
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0229
-1 0 1 0.0229
0 1 -1 0.0503
0 -1 -1 0.0484
1 3 5 0.0421
4 -2 6 0.0652

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'crystallized from DCM / hexanes'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.0000 0.0000 -1.0000 -0.1561 -0.0098 0.0339
-1.0000 -0.0000 1.0000 0.1561 0.0098 -0.0339
-0.5000 1.0000 -1.0000 0.0065 0.1278 0.1597
0.0000 -1.0000 -1.0000 -0.0377 -0.1529 0.0959
1.0000 3.0000 5.0000 0.0880 0.4849 -0.5807
4.0000 -2.0000 6.0000 -0.1756 -0.2011 -0.9807

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29659
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.426
_diffrn_reflns_theta_min         4.593
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00 -74.00   0.50    0.30    --  -45.29-149.00  69.00   52
  2  ω    -84.00 -16.00   0.50    0.30    --  -45.29 123.00 -47.00  136
  3  ω    -89.00 -64.00   0.50    0.30    --  -45.29 149.00 115.00   50
  4  ω   -119.00 -73.00   0.50    0.30    --  -45.29-123.00-127.00   92
  5  ω     53.00  78.00   0.50    0.30    --   45.29-149.00  69.00   50
  6  ω     33.00  87.00   0.50    0.30    --   45.29-123.00-127.00  108
  7  ω   -116.00 -90.00   0.50    1.50    --  -88.50-123.00-127.00   52
  8  ω    -76.00 -51.00   0.50    1.50    --  -88.50 123.00 -47.00   50
  9  ω   -129.00-103.00   0.50    1.50    --  -88.50-149.00  69.00   52
 10  ω    100.00 125.00   0.50    1.50    --  110.00 149.00 115.00   50
 11  ω     46.00  77.00   0.50    1.50    --  110.00-123.00-127.00   62
 12  ω    146.00 171.00   0.50    1.50    --  110.00 123.00 -47.00   50
 13  ω     87.00 120.00   0.50    1.50    --  110.00-149.00  69.00   66
 14  ω   -119.00 -88.00   0.50    0.30    --  -45.29 -77.00 -60.00   62
 15  ω   -119.00 -88.00   0.50    0.30    --  -45.29 -77.00 -30.00   62
 16  ω   -119.00 -80.00   0.50    0.30    --  -45.29-125.00 120.00   78
 17  ω     88.00 119.00   0.50    0.30    --   45.29  77.00 -60.00   62
 18  ω     86.00 116.00   0.50    0.30    --   45.29  77.00  30.00   60
 19  ω     88.00 119.00   0.50    0.30    --   45.29  77.00 -90.00   62
 20  ω     92.00 118.00   0.50    0.30    --   45.29  77.00 -30.00   52
 21  ω     86.00 119.00   0.50    0.30    --   45.29  77.00   0.00   66
 22  ω    -53.00 -19.00   0.50    1.50    --  -88.50  45.00 120.00   68
 23  ω   -158.00-108.00   0.50    1.50    --  -88.50 -77.00 150.00  100
 24  ω    -53.00 -15.00   0.50    1.50    --  -88.50  45.00 150.00   76
 25  ω     39.00  71.00   0.50    1.50    --  110.00-125.00 -90.00   64
 26  ω     72.00  98.00   0.50    1.50    --  110.00-125.00 150.00   52
 27  ω     82.00 112.00   0.50    1.50    --  110.00-125.00 -90.00   60
 28  ω     38.00  92.00   0.50    1.50    --  110.00 -77.00 120.00  108
 29  ω     85.00 139.00   0.50    1.50    --  110.00  77.00  30.00  108
 30  ω     41.00  69.00   0.50    1.50    --  110.00 -61.00-180.00   56
 31  ω     58.00 102.00   0.50    1.50    --  110.00 -77.00  30.00   88
 32  ω     86.00 112.00   0.50    1.50    --  110.00-125.00-180.00   52
 33  ω     92.00 171.00   0.50    1.50    --  110.00  30.00 -30.00  158
 34  ω     48.00 102.00   0.50    1.50    --  110.00 -94.00  30.00  108
 35  ω    102.00 128.00   0.50    1.50    --  110.00  45.00  90.00   52
 36  ω     40.00  84.00   0.50    1.50    --  110.00 -94.00 -60.00   88
 37  ω     38.00  84.00   0.50    1.50    --  110.00-125.00  30.00   92
 38  ω     39.00  80.00   0.50    1.50    --  110.00 -94.00 120.00   82
 39  ω     81.00 106.00   0.50    1.50    --  110.00 -94.00 120.00   50
 40  ω     40.00  66.00   0.50    1.50    --  110.00-125.00 -60.00   52
 41  ω     86.00 112.00   0.50    1.50    --  110.00-125.00 -60.00   52
 42  ω     42.00 101.00   0.50    1.50    --  110.00 -77.00 -60.00  118
 43  ω     92.00 146.00   0.50    1.50    --  110.00  61.00 150.00  108
 44  ω     66.00  92.00   0.50    1.50    --  110.00 -77.00-150.00   52
 45  ω    104.00 175.00   0.50    1.50    --  110.00  30.00   0.00  142
 46  ω     76.00 112.00   0.50    1.50    --  110.00-125.00-150.00   72
 47  ω     47.00  72.00   0.50    1.50    --  110.00 -77.00 -30.00   50
 48  ω     38.00  78.00   0.50    1.50    --  110.00-125.00-150.00   80
 49  ω     70.00  96.00   0.50    1.50    --  110.00 -77.00-180.00   52
 50  ω     43.00  69.00   0.50    1.50    --  110.00 -77.00-180.00   52
 51  ω    109.00 173.00   0.50    1.50    --  110.00  61.00-150.00  128
 52  ω     57.00 106.00   0.50    1.50    --  110.00 -94.00  90.00   98
 53  ω     38.00  68.00   0.50    1.50    --  110.00 -61.00   0.00   60
 54  ω     74.00 112.00   0.50    1.50    --  110.00-125.00 -30.00   76
 55  ω     42.00  67.00   0.50    1.50    --  110.00-125.00-180.00   50
 56  ω     46.00  72.00   0.50    1.50    --  110.00-125.00 -30.00   52
 57  ω     83.00 112.00   0.50    1.50    --  110.00-125.00  90.00   58
 58  ω     57.00 112.00   0.50    1.50    --  110.00-125.00  60.00  110
 59  ω    149.00 178.00   0.50    1.50    --  110.00  45.00  90.00   58
 60  ω     92.00 143.00   0.50    1.50    --  110.00  15.00 -30.00  102
 61  ω     63.00 106.00   0.50    1.50    --  110.00 -94.00  60.00   86
 62  ω     41.00  67.00   0.50    1.50    --  110.00-125.00   0.00   52
 63  ω     85.00 112.00   0.50    1.50    --  110.00-125.00   0.00   54
 64  ω    106.00 151.00   0.50    1.50    --  110.00 125.00-120.00   90
 65  ω     95.00 126.00   0.50    1.50    --  110.00 125.00  30.00   62
 66  ω    131.00 157.00   0.50    1.50    --  110.00 125.00  30.00   52
 67  ω    140.00 168.00   0.50    1.50    --  110.00  45.00-120.00   56
 68  ω     96.00 126.00   0.50    1.50    --  110.00  45.00 -30.00   60
 69  ω    139.00 177.00   0.50    1.50    --  110.00  45.00 -30.00   76
 70  ω    104.00 139.00   0.50    1.50    --  110.00  45.00 120.00   70
 71  ω    145.00 172.00   0.50    1.50    --  110.00  45.00 120.00   54
 72  ω     92.00 151.00   0.50    1.50    --  110.00  30.00 120.00  118
 73  ω    109.00 154.00   0.50    1.50    --  110.00  30.00 150.00   90
 74  ω     39.00  89.00   0.50    1.50    --  110.00 -94.00 -90.00  100
 75  ω     43.00  68.00   0.50    1.50    --  110.00 -61.00 120.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'Rigaku Oxford Diffraction XtaLAB Synergy S with HyPix-6000HE detector'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1124336000
_diffrn_orient_matrix_UB_12      -0.0059984000
_diffrn_orient_matrix_UB_13      0.0436927000
_diffrn_orient_matrix_UB_21      0.0022060000
_diffrn_orient_matrix_UB_22      0.1409258000
_diffrn_orient_matrix_UB_23      0.0119834000
_diffrn_orient_matrix_UB_31      -0.0751153000
_diffrn_orient_matrix_UB_32      0.0131223000
_diffrn_orient_matrix_UB_33      -0.1089965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3272
_reflns_number_total             3497
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.049
_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)+(0.0391P)²+0.6811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0901
_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 Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_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
B1 B 0.50944(10) 0.60821(11) 0.22055(9) 0.0189(2) Uani 1 1 d . . . . .
O1 O 0.62931(6) 0.60660(7) 0.25262(6) 0.02060(18) Uani 1 1 d . . . . .
O2 O 0.47152(7) 0.67916(8) 0.13496(6) 0.02264(18) Uani 1 1 d . . . . .
O3 O 0.59758(7) 0.29743(7) 0.49850(6) 0.02225(18) Uani 1 1 d . . . . .
O4 O 0.42497(7) 0.25113(7) 0.53969(6) 0.02184(18) Uani 1 1 d . . . . .
N1 N 0.42428(7) 0.38897(8) 0.41594(7) 0.01768(19) Uani 1 1 d . . . . .
C1 C 0.67798(9) 0.66481(10) 0.17204(8) 0.0205(2) Uani 1 1 d . . . . .
C2 C 0.57386(10) 0.74729(11) 0.11729(9) 0.0230(2) Uani 1 1 d . . . . .
C3 C 0.78834(10) 0.73383(12) 0.22189(9) 0.0260(2) Uani 1 1 d . . . . .
H3A H 0.769262 0.794081 0.270588 0.039 Uiso 1 1 calc R U . . .
H3B H 0.820448 0.776445 0.169071 0.039 Uiso 1 1 calc R U . . .
H3C H 0.846582 0.675532 0.258219 0.039 Uiso 1 1 calc R U . . .
C4 C 0.70771(10) 0.56217(11) 0.10420(9) 0.0259(2) Uani 1 1 d . . . . .
H4A H 0.761268 0.503714 0.146048 0.039 Uiso 1 1 calc R U . . .
H4B H 0.745449 0.597158 0.051498 0.039 Uiso 1 1 calc R U . . .
H4C H 0.635553 0.519527 0.071358 0.039 Uiso 1 1 calc R U . . .
C5 C 0.57022(11) 0.87251(12) 0.16768(11) 0.0321(3) Uani 1 1 d . . . . .
H5A H 0.496048 0.913643 0.138131 0.048 Uiso 1 1 calc R U . . .
H5B H 0.635963 0.922794 0.155811 0.048 Uiso 1 1 calc R U . . .
H5C H 0.576309 0.861661 0.241515 0.048 Uiso 1 1 calc R U . . .
C6 C 0.56413(11) 0.76161(13) 0.00234(10) 0.0327(3) Uani 1 1 d . . . . .
H6A H 0.551332 0.680810 -0.030642 0.049 Uiso 1 1 calc R U . . .
H6B H 0.636829 0.797466 -0.010735 0.049 Uiso 1 1 calc R U . . .
H6C H 0.497963 0.815761 -0.025616 0.049 Uiso 1 1 calc R U . . .
C7 C 0.42548(9) 0.53555(10) 0.27481(8) 0.0175(2) Uani 1 1 d . . . . .
C8 C 0.47630(9) 0.46203(9) 0.35251(8) 0.0171(2) Uani 1 1 d . . . . .
H8 H 0.559638 0.459792 0.365874 0.021 Uiso 1 1 calc R U . . .
C9 C 0.49257(9) 0.31162(10) 0.48571(8) 0.0183(2) Uani 1 1 d . . . . .
C10 C 0.30240(10) 0.27978(11) 0.50051(9) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.264425 0.306441 0.556751 0.028 Uiso 1 1 calc R U . . .
H10B H 0.260191 0.206891 0.466824 0.028 Uiso 1 1 calc R U . . .
C11 C 0.30101(9) 0.38389(10) 0.42311(8) 0.0207(2) Uani 1 1 d . . . . .
H11A H 0.249806 0.363827 0.356160 0.025 Uiso 1 1 calc R U . . .
H11B H 0.274945 0.462377 0.448700 0.025 Uiso 1 1 calc R U . . .
C12 C 0.29595(9) 0.54956(9) 0.23752(8) 0.0165(2) Uani 1 1 d . . . . .
C13 C 0.23357(9) 0.64160(10) 0.27574(8) 0.0196(2) Uani 1 1 d . . . . .
H13 H 0.273449 0.696251 0.326850 0.024 Uiso 1 1 calc R U . . .
C14 C 0.11314(9) 0.65386(10) 0.23942(8) 0.0210(2) Uani 1 1 d . . . . .
H14 H 0.071077 0.716348 0.266271 0.025 Uiso 1 1 calc R U . . .
C15 C 0.05427(9) 0.57507(11) 0.16409(8) 0.0213(2) Uani 1 1 d . . . . .
H15 H -0.027958 0.583462 0.139544 0.026 Uiso 1 1 calc R U . . .
C16 C 0.11589(10) 0.48405(10) 0.12475(8) 0.0221(2) Uani 1 1 d . . . . .
H16 H 0.075979 0.430142 0.073039 0.026 Uiso 1 1 calc R U . . .
C17 C 0.23617(9) 0.47193(10) 0.16118(8) 0.0195(2) Uani 1 1 d . . . . .
H17 H 0.278111 0.409913 0.133659 0.023 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
B1 O1 1.3728(14) . ?
B1 O2 1.3729(14) . ?
B1 C7 1.5484(15) . ?
O1 C1 1.4594(12) . ?
O2 C2 1.4633(13) . ?
O3 C9 1.2091(13) . ?
O4 C9 1.3439(13) . ?
O4 C10 1.4486(13) . ?
N1 C8 1.3880(13) . ?
N1 C9 1.3781(13) . ?
N1 C11 1.4593(13) . ?
C1 C2 1.5623(15) . ?
C1 C3 1.5176(15) . ?
C1 C4 1.5213(16) . ?
C2 C5 1.5229(17) . ?
C2 C6 1.5221(16) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3453(15) . ?
C7 C12 1.4949(13) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5301(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3939(15) . ?
C12 C17 1.3930(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3920(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3887(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3878(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3905(15) . ?
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
O1 B1 O2 113.42(9) . . ?
O1 B1 C7 123.20(10) . . ?
O2 B1 C7 123.37(10) . . ?
B1 O1 C1 106.85(8) . . ?
B1 O2 C2 106.63(8) . . ?
C9 O4 C10 110.13(8) . . ?
C8 N1 C11 128.40(9) . . ?
C9 N1 C8 119.83(9) . . ?
C9 N1 C11 111.74(9) . . ?
O1 C1 C2 102.19(8) . . ?
O1 C1 C3 108.33(9) . . ?
O1 C1 C4 106.92(9) . . ?
C3 C1 C2 115.20(10) . . ?
C3 C1 C4 110.30(9) . . ?
C4 C1 C2 113.15(9) . . ?
O2 C2 C1 102.30(8) . . ?
O2 C2 C5 106.46(9) . . ?
O2 C2 C6 108.73(9) . . ?
C5 C2 C1 113.37(10) . . ?
C6 C2 C1 114.73(10) . . ?
C6 C2 C5 110.51(10) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 B1 116.35(9) . . ?
C8 C7 C12 124.71(9) . . ?
C12 C7 B1 118.93(9) . . ?
N1 C8 H8 115.4 . . ?
C7 C8 N1 129.20(9) . . ?
C7 C8 H8 115.4 . . ?
O3 C9 O4 123.34(10) . . ?
O3 C9 N1 126.75(10) . . ?
O4 C9 N1 109.91(9) . . ?
O4 C10 H10A 110.5 . . ?
O4 C10 H10B 110.5 . . ?
O4 C10 C11 105.93(8) . . ?
H10A C10 H10B 108.7 . . ?
C11 C10 H10A 110.5 . . ?
C11 C10 H10B 110.5 . . ?
N1 C11 C10 101.50(8) . . ?
N1 C11 H11A 111.5 . . ?
N1 C11 H11B 111.5 . . ?
C10 C11 H11A 111.5 . . ?
C10 C11 H11B 111.5 . . ?
H11A C11 H11B 109.3 . . ?
C13 C12 C7 121.19(9) . . ?
C17 C12 C7 119.90(9) . . ?
C17 C12 C13 118.88(9) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.36(10) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.23(10) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.82(10) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.85(10) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.85(10) . . ?
C16 C17 H17 119.6 . . ?

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
B1 O1 C1 C2 23.97(11) . . . . ?
B1 O1 C1 C3 146.01(9) . . . . ?
B1 O1 C1 C4 -95.12(10) . . . . ?
B1 O2 C2 C1 23.72(11) . . . . ?
B1 O2 C2 C5 -95.47(10) . . . . ?
B1 O2 C2 C6 145.46(10) . . . . ?
B1 C7 C8 N1 178.40(10) . . . . ?
B1 C7 C12 C13 -88.60(12) . . . . ?
B1 C7 C12 C17 89.58(12) . . . . ?
O1 B1 O2 C2 -9.74(12) . . . . ?
O1 B1 C7 C8 -4.55(16) . . . . ?
O1 B1 C7 C12 176.36(10) . . . . ?
O1 C1 C2 O2 -28.81(10) . . . . ?
O1 C1 C2 C5 85.41(11) . . . . ?
O1 C1 C2 C6 -146.34(10) . . . . ?
O2 B1 O1 C1 -10.16(12) . . . . ?
O2 B1 C7 C8 174.55(10) . . . . ?
O2 B1 C7 C12 -4.55(16) . . . . ?
O4 C10 C11 N1 8.50(11) . . . . ?
C3 C1 C2 O2 -146.02(9) . . . . ?
C3 C1 C2 C5 -31.80(13) . . . . ?
C3 C1 C2 C6 96.45(12) . . . . ?
C4 C1 C2 O2 85.79(10) . . . . ?
C4 C1 C2 C5 -159.99(10) . . . . ?
C4 C1 C2 C6 -31.74(14) . . . . ?
C7 B1 O1 C1 169.01(10) . . . . ?
C7 B1 O2 C2 171.09(10) . . . . ?
C7 C12 C13 C14 179.44(10) . . . . ?
C7 C12 C17 C16 -179.43(10) . . . . ?
C8 N1 C9 O3 -1.03(16) . . . . ?
C8 N1 C9 O4 179.19(9) . . . . ?
C8 N1 C11 C10 176.09(10) . . . . ?
C8 C7 C12 C13 92.39(13) . . . . ?
C8 C7 C12 C17 -89.43(13) . . . . ?
C9 O4 C10 C11 -8.55(12) . . . . ?
C9 N1 C8 C7 174.22(10) . . . . ?
C9 N1 C11 C10 -6.13(11) . . . . ?
C10 O4 C9 O3 -174.96(10) . . . . ?
C10 O4 C9 N1 4.83(12) . . . . ?
C11 N1 C8 C7 -8.15(18) . . . . ?
C11 N1 C9 O3 -179.03(10) . . . . ?
C11 N1 C9 O4 1.19(12) . . . . ?
C12 C7 C8 N1 -2.56(18) . . . . ?
C12 C13 C14 C15 -0.56(16) . . . . ?
C13 C12 C17 C16 -1.21(15) . . . . ?
C13 C14 C15 C16 -0.17(16) . . . . ?
C14 C15 C16 C17 0.21(16) . . . . ?
C15 C16 C17 C12 0.49(16) . . . . ?
C17 C12 C13 C14 1.24(15) . . . . ?

_olex2_date_sample_data_collection 2021-09-01
_olex2_date_sample_submission    2021-08-27
_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop with Paratone oil'
_olex2_submission_original_sample_id SJ-10-001
_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 1.799
_oxdiff_exptl_absorpt_empirical_full_min 0.628
####################################################################### 
# 
# 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_cs2803
_database_code_depnum_ccdc_archive 'CCDC 2193674'
loop_
_audit_author_name
_audit_author_address
'Carla Slebodnick'
;Virginia Tech
United States of America
;
_audit_update_record             
;
2022-07-29 deposited with the CCDC.	2022-11-10 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
swethajos16@vt.edu
slebod@vt.edu
santosw@vt.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cl F3 N O2'
_chemical_formula_sum            'C12 H9 Cl F3 N O2'
_chemical_formula_weight         291.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H9 Cl F3 N O2'
_chemical_oxdiff_usercomment     'Swetha Jos / Santos (SJ-10-CF3-1)'
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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.56080(10)
_cell_length_b                   11.5629(2)
_cell_length_c                   13.4651(2)
_cell_angle_alpha                94.3210(10)
_cell_angle_beta                 106.5730(10)
_cell_angle_gamma                103.1750(10)
_cell_volume                     1229.73(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    35952
_cell_measurement_temperature    99.99(11)
_cell_measurement_theta_max      38.0740
_cell_measurement_theta_min      2.5570
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.455
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0249
0 -1 -1 0.0249
0 2 -5 0.0996
0 -2 5 0.0996
5 -2 -2 0.1451
-5 2 2 0.1451
-1 2 -5 0.1047

_exptl_crystal_recrystallization_method 'crystallized from DCM / hexanes'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0006 1.0003 1.0000 -0.0158 0.0872 0.0190
0.0006 -1.0003 -1.0000 0.0158 -0.0872 -0.0190
0.0007 1.9995 -5.0000 -0.1966 -0.1661 0.1288
-0.0007 -1.9995 5.0000 0.1966 0.1661 -0.1288
5.0007 -2.0003 -2.0009 -0.2194 0.0227 -0.3521
-5.0007 2.0003 2.0009 0.2194 -0.0227 0.3521
-0.9991 1.9994 -4.9998 -0.1465 -0.2055 0.1916

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            87793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        36.000
_diffrn_reflns_theta_max         38.137
_diffrn_reflns_theta_min         2.571
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(11)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  74.00   0.50   13.00    --   29.43-108.00  16.00  148
  2  ω    -74.00 -21.00   0.50   13.00    --  -30.13 108.00 112.00  106
  3  ω      7.00 107.00   0.50   13.00    --   29.43  38.00 -30.00  200
  4  ω    -50.00   3.00   0.50   13.00    --   29.43 -19.00  30.00  106
  5  ω      8.00 104.00   0.50   13.00    --   29.43  57.00-180.00  192
  6  ω      1.00  41.00   0.50   13.00    --   29.43  77.00 -30.00   80
  7  ω     39.00 109.00   0.50   13.00    --   29.43-178.00   0.00  140
  8  ω      7.00 107.00   0.50   13.00    --   29.43  38.00 120.00  200
  9  ω      1.00  41.00   0.50   13.00    --   29.43  77.00 120.00   80
 10  ω      7.00 107.00   0.50   13.00    --   29.43  38.00  30.00  200
 11  ω    -18.00  69.00   0.50   13.00    --   29.43 -99.00-150.00  174
 12  ω      1.00  41.00   0.50   13.00    --   29.43  77.00-120.00   80
 13  ω    -41.00  58.00   0.50   13.00    --   29.43 -77.00  90.00  198
 14  ω    -18.00  69.00   0.50   13.00    --   29.43 -99.00 -90.00  174
 15  ω      1.00  41.00   0.50   13.00    --   29.43  77.00  30.00   80
 16  ω    -48.00  20.00   0.50   13.00    --   29.43 -38.00   0.00  136
 17  ω      1.00  41.00   0.50   13.00    --   29.43  77.00 -90.00   80
 18  ω    -50.00   3.00   0.50   13.00    --   29.43 -19.00 150.00  106
 19  ω      8.00 104.00   0.50   13.00    --   29.43  57.00 150.00  192
 20  ω   -108.00 -63.00   0.50   13.00    --  -30.13-178.00 -90.00   90
 21  ω    -50.00   3.00   0.50   13.00    --   29.43 -19.00  90.00  106
 22  ω    -18.00  69.00   0.50   13.00    --   29.43 -99.00   0.00  174
 23  ω    -50.00   3.00   0.50   13.00    --   29.43 -19.00  60.00  106
 24  ω    -44.00  42.00   0.50   13.00    --   29.43 -57.00-150.00  172
 25  ω    -18.00  69.00   0.50   13.00    --   29.43 -99.00  60.00  174
 26  ω      1.00  41.00   0.50   13.00    --   29.43  77.00-180.00   80
 27  ω    -41.00  -1.00   0.50   13.00    --  -30.13 -77.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0501867000
_diffrn_orient_matrix_UB_12      -0.0393823000
_diffrn_orient_matrix_UB_13      0.0235733000
_diffrn_orient_matrix_UB_21      0.0394275000
_diffrn_orient_matrix_UB_22      0.0385742000
_diffrn_orient_matrix_UB_23      0.0486432000
_diffrn_orient_matrix_UB_31      -0.0628149000
_diffrn_orient_matrix_UB_32      0.0319691000
_diffrn_orient_matrix_UB_33      -0.0129871000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9920
_reflns_number_total             13007
_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       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.385
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         13007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.037
_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)+(0.0698P)²+0.3505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1323
_refine_ls_wR_factor_ref         0.1413
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C11(H11), C12(H12), C16(H16), C20(H20), C21(H21),
 C23(H23), C24(H24)
;
_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
Cl1 Cl 0.26896(4) -0.11318(2) 0.57785(2) 0.03094(6) Uani 1 1 d . . . . .
F1 F 0.51195(17) 0.60489(8) 0.74799(8) 0.0630(3) Uani 1 1 d . . . . .
F2 F 0.45574(12) 0.44285(8) 0.81329(6) 0.04219(19) Uani 1 1 d . . . . .
F3 F 0.65868(12) 0.47712(11) 0.74709(8) 0.0550(3) Uani 1 1 d . . . . .
O1 O 0.11636(12) 0.62307(8) 0.44093(7) 0.03176(17) Uani 1 1 d . . . . .
O2 O -0.01529(11) 0.45562(7) 0.32352(7) 0.02854(15) Uani 1 1 d . . . . .
N1 N 0.18982(11) 0.44395(7) 0.46400(7) 0.02271(14) Uani 1 1 d . . . . .
C1 C 0.09962(13) 0.51800(9) 0.41250(8) 0.02446(17) Uani 1 1 d . . . . .
C2 C 0.01397(16) 0.33834(10) 0.30454(9) 0.0298(2) Uani 1 1 d . . . . .
H2A H 0.074620 0.336843 0.252089 0.036 Uiso 1 1 calc R U . . .
H2B H -0.094041 0.275122 0.279081 0.036 Uiso 1 1 calc R U . . .
C3 C 0.12140(14) 0.32001(9) 0.41081(8) 0.02590(18) Uani 1 1 d . . . . .
H3A H 0.052044 0.270217 0.447379 0.031 Uiso 1 1 calc R U . . .
H3B H 0.211996 0.282831 0.404159 0.031 Uiso 1 1 calc R U . . .
C4 C 0.30463(13) 0.48582(9) 0.56264(8) 0.02452(17) Uani 1 1 d . . . . .
H4 H 0.332163 0.569871 0.585170 0.029 Uiso 1 1 calc R U . . .
C5 C 0.38167(14) 0.42193(9) 0.63025(9) 0.02621(18) Uani 1 1 d . . . . .
C6 C 0.50501(19) 0.48864(11) 0.73510(10) 0.0359(2) Uani 1 1 d . . . . .
C7 C 0.35602(12) 0.28923(9) 0.61861(8) 0.02318(16) Uani 1 1 d . . . . .
C8 C 0.47808(12) 0.23674(10) 0.59926(8) 0.02449(17) Uani 1 1 d . . . . .
H8 H 0.578851 0.286074 0.592864 0.029 Uiso 1 1 calc R U . . .
C9 C 0.45334(13) 0.11323(10) 0.58932(8) 0.02479(17) Uani 1 1 d . . . . .
H9 H 0.536921 0.077721 0.576662 0.030 Uiso 1 1 calc R U . . .
C10 C 0.30510(13) 0.04192(9) 0.59806(8) 0.02322(16) Uani 1 1 d . . . . .
C11 C 0.18353(13) 0.09192(10) 0.61961(9) 0.02624(18) Uani 1 1 d . . . . .
H11 H 0.083767 0.042243 0.626978 0.031 Uiso 1 1 calc R U . . .
C12 C 0.21014(13) 0.21581(10) 0.63022(9) 0.02622(18) Uani 1 1 d . . . . .
H12 H 0.128182 0.251135 0.645571 0.031 Uiso 1 1 calc R U . . .
Cl2 Cl 1.22167(5) 0.50182(3) 0.98057(3) 0.04573(9) Uani 1 1 d . . . . .
F4 F 0.67347(12) -0.17871(7) 0.71719(9) 0.0499(2) Uani 1 1 d . . . . .
F5 F 0.79756(10) -0.03346(7) 0.65417(6) 0.03316(15) Uani 1 1 d . . . . .
F6 F 0.93408(12) -0.08783(9) 0.79337(7) 0.0440(2) Uani 1 1 d . . . . .
O3 O 0.29034(11) -0.11240(9) 0.87183(7) 0.03172(17) Uani 1 1 d . . . . .
O4 O 0.28977(10) 0.07735(9) 0.92265(7) 0.03218(17) Uani 1 1 d . . . . .
N2 N 0.50771(10) 0.04969(8) 0.87422(7) 0.02283(15) Uani 1 1 d . . . . .
C13 C 0.35563(12) -0.00589(11) 0.88749(8) 0.02509(18) Uani 1 1 d . . . . .
C14 C 0.39605(16) 0.19600(12) 0.93179(11) 0.0339(2) Uani 1 1 d . . . . .
H14A H 0.435586 0.236752 1.005207 0.041 Uiso 1 1 calc R U . . .
H14B H 0.333477 0.244854 0.886598 0.041 Uiso 1 1 calc R U . . .
C15 C 0.54569(13) 0.17998(10) 0.89670(9) 0.02621(18) Uani 1 1 d . . . . .
H15A H 0.549304 0.217596 0.833453 0.031 Uiso 1 1 calc R U . . .
H15B H 0.654156 0.213821 0.953156 0.031 Uiso 1 1 calc R U . . .
C16 C 0.58581(12) -0.01852(9) 0.82550(8) 0.02284(16) Uani 1 1 d . . . . .
H16 H 0.526861 -0.100521 0.800915 0.027 Uiso 1 1 calc R U . . .
C17 C 0.73566(12) 0.01820(9) 0.80905(8) 0.02215(16) Uani 1 1 d . . . . .
C18 C 0.78645(14) -0.07129(10) 0.74445(9) 0.02655(18) Uani 1 1 d . . . . .
C19 C 0.85981(11) 0.13651(9) 0.84983(7) 0.02066(15) Uani 1 1 d . . . . .
C20 C 0.94207(13) 0.16761(11) 0.95772(8) 0.02739(19) Uani 1 1 d . . . . .
H20 H 0.920898 0.111610 1.003503 0.033 Uiso 1 1 calc R U . . .
C21 C 1.05428(14) 0.27955(13) 0.99837(9) 0.0313(2) Uani 1 1 d . . . . .
H21 H 1.109459 0.300594 1.071699 0.038 Uiso 1 1 calc R U . . .
C22 C 1.08504(13) 0.36033(11) 0.93092(9) 0.02747(19) Uani 1 1 d . . . . .
C23 C 1.00951(13) 0.33046(10) 0.82351(8) 0.02598(18) Uani 1 1 d . . . . .
H23 H 1.034125 0.385892 0.777976 0.031 Uiso 1 1 calc R U . . .
C24 C 0.89713(13) 0.21811(9) 0.78334(8) 0.02311(16) Uani 1 1 d . . . . .
H24 H 0.845136 0.196652 0.709755 0.028 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
Cl1 C10 1.7354(11) . ?
F1 C6 1.3278(16) . ?
F2 C6 1.3425(15) . ?
F3 C6 1.3177(19) . ?
O1 C1 1.2092(13) . ?
O2 C1 1.3407(14) . ?
O2 C2 1.4513(14) . ?
N1 C1 1.3769(13) . ?
N1 C3 1.4605(13) . ?
N1 C4 1.3806(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5239(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3381(15) . ?
C5 C6 1.5223(17) . ?
C5 C7 1.4891(15) . ?
C7 C8 1.3960(15) . ?
C7 C12 1.3974(14) . ?
C8 H8 0.9500 . ?
C8 C9 1.3855(15) . ?
C9 H9 0.9500 . ?
C9 C10 1.3881(14) . ?
C10 C11 1.3867(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3879(15) . ?
C12 H12 0.9500 . ?
Cl2 C22 1.7345(12) . ?
F4 C18 1.3395(13) . ?
F5 C18 1.3435(13) . ?
F6 C18 1.3123(14) . ?
O3 C13 1.2056(15) . ?
O4 C13 1.3415(14) . ?
O4 C14 1.4377(16) . ?
N2 C13 1.3815(13) . ?
N2 C15 1.4555(14) . ?
N2 C16 1.3828(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5294(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C17 1.3427(13) . ?
C17 C18 1.5171(15) . ?
C17 C19 1.4812(14) . ?
C19 C20 1.3993(14) . ?
C19 C24 1.3953(13) . ?
C20 H20 0.9500 . ?
C20 C21 1.3872(18) . ?
C21 H21 0.9500 . ?
C21 C22 1.3853(18) . ?
C22 C23 1.3851(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.3904(15) . ?
C24 H24 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
C1 O2 C2 109.60(8) . . ?
C1 N1 C3 110.93(9) . . ?
C1 N1 C4 119.83(9) . . ?
C4 N1 C3 128.05(9) . . ?
O1 C1 O2 123.43(10) . . ?
O1 C1 N1 126.98(10) . . ?
O2 C1 N1 109.59(9) . . ?
O2 C2 H2A 110.8 . . ?
O2 C2 H2B 110.8 . . ?
O2 C2 C3 104.55(9) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
N1 C3 C2 100.81(8) . . ?
N1 C3 H3A 111.6 . . ?
N1 C3 H3B 111.6 . . ?
C2 C3 H3A 111.6 . . ?
C2 C3 H3B 111.6 . . ?
H3A C3 H3B 109.4 . . ?
N1 C4 H4 116.2 . . ?
C5 C4 N1 127.64(10) . . ?
C5 C4 H4 116.2 . . ?
C4 C5 C6 118.10(10) . . ?
C4 C5 C7 127.85(10) . . ?
C7 C5 C6 113.97(9) . . ?
F1 C6 F2 106.77(12) . . ?
F1 C6 C5 112.74(11) . . ?
F2 C6 C5 109.50(10) . . ?
F3 C6 F1 108.55(13) . . ?
F3 C6 F2 107.33(11) . . ?
F3 C6 C5 111.69(11) . . ?
C8 C7 C5 121.00(9) . . ?
C8 C7 C12 119.14(9) . . ?
C12 C7 C5 119.83(9) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.49(9) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.28(9) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 Cl1 119.15(8) . . ?
C11 C10 Cl1 119.43(8) . . ?
C11 C10 C9 121.40(10) . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.84(9) . . ?
C12 C11 H11 120.6 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.81(10) . . ?
C11 C12 H12 119.6 . . ?
C13 O4 C14 110.69(8) . . ?
C13 N2 C15 111.98(8) . . ?
C13 N2 C16 118.64(9) . . ?
C16 N2 C15 128.21(8) . . ?
O3 C13 O4 124.03(9) . . ?
O3 C13 N2 126.50(10) . . ?
O4 C13 N2 109.47(10) . . ?
O4 C14 H14A 110.5 . . ?
O4 C14 H14B 110.5 . . ?
O4 C14 C15 106.36(9) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.5 . . ?
C15 C14 H14B 110.5 . . ?
N2 C15 C14 101.42(9) . . ?
N2 C15 H15A 111.5 . . ?
N2 C15 H15B 111.5 . . ?
C14 C15 H15A 111.5 . . ?
C14 C15 H15B 111.5 . . ?
H15A C15 H15B 109.3 . . ?
N2 C16 H16 116.4 . . ?
C17 C16 N2 127.26(10) . . ?
C17 C16 H16 116.4 . . ?
C16 C17 C18 117.10(9) . . ?
C16 C17 C19 126.80(9) . . ?
C19 C17 C18 116.08(8) . . ?
F4 C18 F5 105.90(10) . . ?
F4 C18 C17 112.40(9) . . ?
F5 C18 C17 111.10(9) . . ?
F6 C18 F4 107.91(10) . . ?
F6 C18 F5 106.64(9) . . ?
F6 C18 C17 112.51(9) . . ?
C20 C19 C17 119.36(9) . . ?
C24 C19 C17 121.68(9) . . ?
C24 C19 C20 118.97(10) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.53(10) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.30(10) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 Cl2 119.95(9) . . ?
C23 C22 Cl2 118.70(9) . . ?
C23 C22 C21 121.36(11) . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.00(10) . . ?
C24 C23 H23 120.5 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.78(9) . . ?
C23 C24 H24 119.6 . . ?

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
Cl1 C10 C11 C12 -176.69(9) . . . . ?
O2 C2 C3 N1 -20.46(11) . . . . ?
N1 C4 C5 C6 179.70(11) . . . . ?
N1 C4 C5 C7 -3.69(19) . . . . ?
C1 O2 C2 C3 19.11(12) . . . . ?
C1 N1 C3 C2 16.29(11) . . . . ?
C1 N1 C4 C5 168.14(11) . . . . ?
C2 O2 C1 O1 171.49(10) . . . . ?
C2 O2 C1 N1 -9.15(12) . . . . ?
C3 N1 C1 O1 173.96(11) . . . . ?
C3 N1 C1 O2 -5.36(12) . . . . ?
C3 N1 C4 C5 1.81(18) . . . . ?
C4 N1 C1 O1 5.45(16) . . . . ?
C4 N1 C1 O2 -173.88(9) . . . . ?
C4 N1 C3 C2 -176.39(10) . . . . ?
C4 C5 C6 F1 3.86(17) . . . . ?
C4 C5 C6 F2 122.56(12) . . . . ?
C4 C5 C6 F3 -118.69(12) . . . . ?
C4 C5 C7 C8 107.59(14) . . . . ?
C4 C5 C7 C12 -74.34(15) . . . . ?
C5 C7 C8 C9 179.54(10) . . . . ?
C5 C7 C12 C11 179.93(10) . . . . ?
C6 C5 C7 C8 -75.68(13) . . . . ?
C6 C5 C7 C12 102.39(12) . . . . ?
C7 C5 C6 F1 -173.22(12) . . . . ?
C7 C5 C6 F2 -54.51(14) . . . . ?
C7 C5 C6 F3 64.24(13) . . . . ?
C7 C8 C9 C10 0.46(16) . . . . ?
C8 C7 C12 C11 -1.95(16) . . . . ?
C8 C9 C10 Cl1 176.20(8) . . . . ?
C8 C9 C10 C11 -1.94(16) . . . . ?
C9 C10 C11 C12 1.44(17) . . . . ?
C10 C11 C12 C7 0.53(17) . . . . ?
C12 C7 C8 C9 1.45(16) . . . . ?
Cl2 C22 C23 C24 -178.67(8) . . . . ?
O4 C14 C15 N2 -1.74(12) . . . . ?
N2 C16 C17 C18 -174.36(10) . . . . ?
N2 C16 C17 C19 7.39(17) . . . . ?
C13 O4 C14 C15 0.12(13) . . . . ?
C13 N2 C15 C14 2.84(12) . . . . ?
C13 N2 C16 C17 -177.43(10) . . . . ?
C14 O4 C13 O3 -179.16(11) . . . . ?
C14 O4 C13 N2 1.70(13) . . . . ?
C15 N2 C13 O3 177.90(11) . . . . ?
C15 N2 C13 O4 -2.99(12) . . . . ?
C15 N2 C16 C17 16.01(17) . . . . ?
C16 N2 C13 O3 9.26(16) . . . . ?
C16 N2 C13 O4 -171.63(9) . . . . ?
C16 N2 C15 C14 170.14(10) . . . . ?
C16 C17 C18 F4 -3.13(14) . . . . ?
C16 C17 C18 F5 115.33(10) . . . . ?
C16 C17 C18 F6 -125.19(11) . . . . ?
C16 C17 C19 C20 66.72(14) . . . . ?
C16 C17 C19 C24 -113.29(12) . . . . ?
C17 C19 C20 C21 -177.63(9) . . . . ?
C17 C19 C24 C23 177.66(9) . . . . ?
C18 C17 C19 C20 -111.54(10) . . . . ?
C18 C17 C19 C24 68.45(12) . . . . ?
C19 C17 C18 F4 175.31(10) . . . . ?
C19 C17 C18 F5 -66.23(12) . . . . ?
C19 C17 C18 F6 53.25(12) . . . . ?
C19 C20 C21 C22 -0.36(16) . . . . ?
C20 C19 C24 C23 -2.35(15) . . . . ?
C20 C21 C22 Cl2 178.70(8) . . . . ?
C20 C21 C22 C23 -1.74(17) . . . . ?
C21 C22 C23 C24 1.76(16) . . . . ?
C22 C23 C24 C19 0.32(16) . . . . ?
C24 C19 C20 C21 2.37(15) . . . . ?

_olex2_exptl_crystal_mounting_method 
'mounted on a nylon loop with perfluoroether oil'
_olex2_submission_original_sample_id SJ-10-CF3-1
_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 1.739
_oxdiff_exptl_absorpt_empirical_full_min 0.654
