# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_TvS
_database_code_depnum_ccdc_archive 'CCDC 2152788'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
5-Fluoro-3-thiomorpholin-4-yl-2,1-benzoxaborol-1(3H)-ol
_chemical_formula_moiety         'C11 H13 B F N O2 S'
_chemical_formula_sum            'C11 H13 B F N O2 S'
_chemical_formula_weight         253.09
_chemical_melting_point          '343-358 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0320(3)
_cell_length_b                   6.2712(3)
_cell_length_c                   21.3774(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.420(4)
_cell_angle_gamma                90
_cell_volume                     1194.52(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4087
_cell_measurement_temperature    293.15
_cell_measurement_theta_max      29.1280
_cell_measurement_theta_min      4.1570
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.42
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.883
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            11317
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         3.389
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.883
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  51.00   1.00   30.00    --   11.71 -99.00   0.00   50
  2  ω    -11.00  85.00   1.00   30.00    --   11.71  38.00-120.00   96
  3  ω     61.00 101.00   1.00   30.00    --   11.71-179.00 150.00   40
  4  ω    -63.00 -37.00   1.00   30.00    --   11.71 -38.00 -90.00   26
  5  ω    -27.00  20.00   1.00   30.00    --   11.71 -38.00 -90.00   47
  6  ω    -69.00  49.00   1.00   30.00    --   11.71 -19.00  60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522562000
_diffrn_orient_matrix_UB_12      -0.0636888000
_diffrn_orient_matrix_UB_13      -0.0130400000
_diffrn_orient_matrix_UB_21      -0.0154284000
_diffrn_orient_matrix_UB_22      0.0584944000
_diffrn_orient_matrix_UB_23      -0.0287236000
_diffrn_orient_matrix_UB_31      0.0580137000
_diffrn_orient_matrix_UB_32      0.0729918000
_diffrn_orient_matrix_UB_33      0.0116287000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2329
_reflns_number_total             2966
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.029
_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)+(0.0409P)²+0.5010P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1048
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.8648(2) 0.4992(3) 0.27987(9) 0.0400(4) Uani 1 1 d . . . . .
C1 C 0.97078(17) 0.5138(3) 0.34451(8) 0.0379(4) Uani 1 1 d . . . . .
C2 C 1.0816(2) 0.3856(3) 0.37847(9) 0.0493(5) Uani 1 1 d . . . . .
H2 H 1.105294 0.254704 0.362178 0.059 Uiso 1 1 calc R U . . .
C3 C 1.1559(2) 0.4542(4) 0.43647(9) 0.0547(5) Uani 1 1 d . . . . .
H3 H 1.229995 0.370171 0.459823 0.066 Uiso 1 1 calc R U . . .
C4 C 1.1191(2) 0.6479(4) 0.45917(8) 0.0508(5) Uani 1 1 d . . . . .
C5 C 1.01031(19) 0.7805(3) 0.42766(8) 0.0436(4) Uani 1 1 d . . . . .
H5 H 0.987173 0.910796 0.444450 0.052 Uiso 1 1 calc R U . . .
C6 C 0.93760(16) 0.7087(3) 0.36969(7) 0.0354(4) Uani 1 1 d . . . . .
C7 C 0.81725(17) 0.8248(3) 0.32535(7) 0.0351(3) Uani 1 1 d . . . . .
H7 H 0.8574(18) 0.953(3) 0.3079(7) 0.031(4) Uiso 1 1 d . . . . .
C8 C 0.61409(18) 0.7111(3) 0.37870(8) 0.0376(4) Uani 1 1 d . . . . .
H8A H 0.686554 0.606564 0.398056 0.045 Uiso 1 1 calc R U . . .
H8B H 0.549304 0.642619 0.343793 0.045 Uiso 1 1 calc R U . . .
C9 C 0.5209(2) 0.7863(3) 0.42710(8) 0.0468(4) Uani 1 1 d . . . . .
H9A H 0.586066 0.854015 0.462050 0.056 Uiso 1 1 calc R U . . .
H9B H 0.474489 0.663991 0.443817 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4944(2) 1.1514(3) 0.35816(10) 0.0486(5) Uani 1 1 d . . . . .
H10A H 0.431667 1.255117 0.332590 0.058 Uiso 1 1 calc R U . . .
H10B H 0.559317 1.228115 0.391284 0.058 Uiso 1 1 calc R U . . .
C11 C 0.58968(18) 1.0364(3) 0.31700(8) 0.0422(4) Uani 1 1 d . . . . .
H11A H 0.525235 0.959037 0.283862 0.051 Uiso 1 1 calc R U . . .
H11B H 0.646712 1.139655 0.296943 0.051 Uiso 1 1 calc R U . . .
F1 F 1.19459(14) 0.7133(3) 0.51632(6) 0.0787(4) Uani 1 1 d . . . . .
N1 N 0.69267(14) 0.8874(2) 0.35450(6) 0.0341(3) Uani 1 1 d . . . . .
O1 O 0.85561(16) 0.3376(2) 0.23776(6) 0.0546(4) Uani 1 1 d . . . . .
H1 H 0.796(3) 0.352(4) 0.2067(13) 0.082 Uiso 1 1 d . U . . .
O2 O 0.77614(12) 0.6779(2) 0.27182(5) 0.0410(3) Uani 1 1 d . . . . .
S1 S 0.37671(5) 0.97211(8) 0.39399(2) 0.04820(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 C1 1.549(3) . ?
B1 O1 1.349(2) . ?
B1 O2 1.372(2) . ?
C1 C2 1.392(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(3) . ?
C4 C5 1.376(3) . ?
C4 F1 1.361(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(2) . ?
C6 C7 1.507(2) . ?
C7 H7 0.980(17) . ?
C7 N1 1.428(2) . ?
C7 O2 1.469(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.512(2) . ?
C8 N1 1.454(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 S1 1.8035(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.511(3) . ?
C10 S1 1.802(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 N1 1.462(2) . ?
O1 H1 0.79(3) . ?

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 C1 126.94(17) . . ?
O1 B1 O2 123.98(16) . . ?
O2 B1 C1 109.06(15) . . ?
C2 C1 B1 135.84(17) . . ?
C6 C1 B1 104.88(14) . . ?
C6 C1 C2 119.27(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.43(19) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.00(17) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 123.91(17) . . ?
F1 C4 C3 118.03(17) . . ?
F1 C4 C5 118.05(19) . . ?
C4 C5 H5 122.0 . . ?
C4 C5 C6 116.06(18) . . ?
C6 C5 H5 122.0 . . ?
C1 C6 C7 111.14(14) . . ?
C5 C6 C1 122.31(16) . . ?
C5 C6 C7 126.54(16) . . ?
C6 C7 H7 111.2(9) . . ?
N1 C7 C6 113.40(13) . . ?
N1 C7 H7 107.9(9) . . ?
N1 C7 O2 113.32(12) . . ?
O2 C7 C6 104.56(13) . . ?
O2 C7 H7 106.2(9) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8B 109.3 . . ?
N1 C8 C9 111.42(14) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
C8 C9 S1 112.33(12) . . ?
H9A C9 H9B 107.9 . . ?
S1 C9 H9A 109.1 . . ?
S1 C9 H9B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C11 C10 S1 112.42(13) . . ?
S1 C10 H10A 109.1 . . ?
S1 C10 H10B 109.1 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C11 C10 110.96(14) . . ?
N1 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C7 N1 C8 114.30(13) . . ?
C7 N1 C11 114.37(13) . . ?
C8 N1 C11 112.17(12) . . ?
B1 O1 H1 116(2) . . ?
B1 O2 C7 110.27(13) . . ?
C10 S1 C9 97.58(8) . . ?

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
O1 H1 S1 0.79(3) 2.56(3) 3.3335(15) 169(3) 2_645 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
B1 C1 C2 C3 179.39(18) . . . . ?
B1 C1 C6 C5 -179.72(15) . . . . ?
B1 C1 C6 C7 -0.55(17) . . . . ?
C1 B1 O2 C7 2.81(18) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 N1 126.07(15) . . . . ?
C1 C6 C7 O2 2.15(17) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 C6 C7 178.89(15) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C4 F1 -179.55(18) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 0.4(2) . . . . ?
C4 C5 C6 C7 -178.59(16) . . . . ?
C5 C6 C7 N1 -54.8(2) . . . . ?
C5 C6 C7 O2 -178.72(15) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C7 N1 C8 -60.60(18) . . . . ?
C6 C7 N1 C11 168.17(14) . . . . ?
C6 C7 O2 B1 -3.04(17) . . . . ?
C8 C9 S1 C10 -50.81(16) . . . . ?
C9 C8 N1 C7 160.74(13) . . . . ?
C9 C8 N1 C11 -66.97(18) . . . . ?
C10 C11 N1 C7 -160.67(14) . . . . ?
C10 C11 N1 C8 67.07(18) . . . . ?
C11 C10 S1 C9 51.24(14) . . . . ?
F1 C4 C5 C6 179.46(16) . . . . ?
N1 C7 O2 B1 -127.02(14) . . . . ?
N1 C8 C9 S1 61.84(17) . . . . ?
O1 B1 C1 C2 0.7(3) . . . . ?
O1 B1 C1 C6 -179.98(17) . . . . ?
O1 B1 O2 C7 -178.55(16) . . . . ?
O2 B1 C1 C2 179.31(18) . . . . ?
O2 B1 C1 C6 -1.39(18) . . . . ?
O2 C7 N1 C8 58.41(17) . . . . ?
O2 C7 N1 C11 -72.82(17) . . . . ?
S1 C10 C11 N1 -62.26(17) . . . . ?

_olex2_submission_original_sample_id MLe-5
_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 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.554
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 molar mixture of dichloromethane and 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_TvO
_database_code_depnum_ccdc_archive 'CCDC 2152789'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_audit_creation_date             2021-07-19
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
5-Fluoro-3-morpholin-4-yl-2,1-benzoxaborol-1(3H)-ol
_chemical_formula_moiety         'C11 H13 B F N O3'
_chemical_formula_sum            'C11 H13 B F N O3'
_chemical_formula_weight         237.03
_chemical_melting_point          '338-378 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.1181(3)
_cell_length_b                   9.4155(4)
_cell_length_c                   10.1914(4)
_cell_angle_alpha                99.383(3)
_cell_angle_beta                 100.605(4)
_cell_angle_gamma                91.220(4)
_cell_volume                     568.53(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.0630
_cell_measurement_theta_min      4.1200
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83316
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            26391
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.259
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -67.00   5.00   1.00  140.00    --  -12.80 123.00-104.31   72
  2  ω    -89.00 -17.00   1.00  140.00    --  -12.80 157.00 112.09   72
  3  ω    -99.00  74.00   1.00  140.00    --  -12.80   0.00 150.00  173
  4  ω    -83.00  14.00   1.00  140.00    --  -12.80 -57.00 -60.00   97
  5  ω    -85.00  10.00   1.00  140.00    --  -12.80 -38.00  90.00   95
  6  ω    -72.00  -1.00   1.00  140.00    --  -12.80 131.00  -3.11   71
  7  ω    -85.00  10.00   1.00  140.00    --  -12.80 -38.00   0.00   95
  8  ω    -62.00 -16.00   1.00  140.00    --   13.11 155.00  80.83   46
  9  ω    -71.00  -1.00   1.00  140.00    --  -12.80 130.00 -50.66   70
 10  ω    -83.00 -12.00   1.00  140.00    --  -12.80 149.00  58.90   71
 11  ω     53.00  99.00   1.00  140.00    --   13.11-179.00-180.00   46
 12  ω     -9.00  86.00   1.00  140.00    --   13.11  38.00-120.00   95
 13  ω     -4.00  53.00   1.00  140.00    --   13.11 -99.00-120.00   57
 14  ω     -4.00  53.00   1.00  140.00    --   13.11 -99.00-180.00   57
 15  ω   -100.00 -34.00   1.00  140.00    --  -12.80-179.00  60.00   66
 16  ω    -71.00  -1.00   1.00  140.00    --  -12.80 130.00-162.09   70
 17  ω    -74.00 100.00   1.00  140.00    --   13.11   0.00-180.00  174
 18  ω    -74.00  28.00   1.00  140.00    --   13.11   0.00-120.00  102
 19  ω    -74.00 100.00   1.00  140.00    --   13.11   0.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0267929000
_diffrn_orient_matrix_UB_12      0.0578730000
_diffrn_orient_matrix_UB_13      -0.0357523000
_diffrn_orient_matrix_UB_21      -0.0974038000
_diffrn_orient_matrix_UB_22      -0.0398049000
_diffrn_orient_matrix_UB_23      -0.0378432000
_diffrn_orient_matrix_UB_31      -0.0612012000
_diffrn_orient_matrix_UB_32      0.0302108000
_diffrn_orient_matrix_UB_33      0.0495210000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2607
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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 (Sheldrick, 2015)'
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.075(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2607
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.065
_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)+(0.0407P)²+0.0895P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0922
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C3(H3)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O2 O 0.43870(14) 0.75362(8) 0.47854(7) 0.0412(2) Uani 1 1 d . . . . .
O3 O 0.11480(14) 1.07888(9) 0.20234(9) 0.0471(2) Uani 1 1 d . . . . .
O1 O 0.80450(15) 0.69699(10) 0.58054(9) 0.0491(2) Uani 1 1 d . . . . .
H1 H 0.794(3) 0.7592(19) 0.6469(18) 0.074 Uiso 1 1 d . U . . .
N1 N 0.19120(15) 0.80563(10) 0.28018(9) 0.0362(2) Uani 1 1 d . . . . .
F1 F 0.32723(19) 0.30198(10) -0.01153(9) 0.0838(3) Uani 1 1 d . . . . .
C6 C 0.37881(19) 0.57797(11) 0.28089(11) 0.0379(3) Uani 1 1 d . . . . .
C7 C 0.27043(19) 0.69789(12) 0.35836(11) 0.0377(3) Uani 1 1 d . . . . .
H7 H 0.143569 0.655907 0.387839 0.045 Uiso 1 1 calc R U . . .
C1 C 0.59002(19) 0.55770(12) 0.35025(11) 0.0392(3) Uani 1 1 d . . . . .
C8 C 0.36484(19) 0.88611(13) 0.23782(12) 0.0416(3) Uani 1 1 d . . . . .
H8A H 0.458445 0.819756 0.193487 0.050 Uiso 1 1 calc R U . . .
H8B H 0.457510 0.944551 0.316355 0.050 Uiso 1 1 calc R U . . .
C11 C 0.0495(2) 0.90640(13) 0.34444(13) 0.0439(3) Uani 1 1 d . . . . .
H11A H 0.137081 0.965594 0.424430 0.053 Uiso 1 1 calc R U . . .
H11B H -0.066925 0.853562 0.372330 0.053 Uiso 1 1 calc R U . . .
C10 C -0.0531(2) 1.00078(14) 0.24641(14) 0.0490(3) Uani 1 1 d . . . . .
H10B H -0.146300 0.941567 0.168587 0.059 Uiso 1 1 calc R U . . .
H10A H -0.146560 1.068112 0.289701 0.059 Uiso 1 1 calc R U . . .
C9 C 0.2579(2) 0.98140(14) 0.14152(13) 0.0498(3) Uani 1 1 d . . . . .
H9B H 0.372967 1.035864 0.114086 0.060 Uiso 1 1 calc R U . . .
H9A H 0.172326 0.921836 0.061015 0.060 Uiso 1 1 calc R U . . .
C2 C 0.7140(2) 0.44900(13) 0.29486(14) 0.0504(3) Uani 1 1 d . . . . .
H2 H 0.855963 0.433931 0.339942 0.060 Uiso 1 1 calc R U . . .
C5 C 0.2850(2) 0.49367(13) 0.15831(12) 0.0483(3) Uani 1 1 d . . . . .
H5 H 0.143103 0.507723 0.112490 0.058 Uiso 1 1 calc R U . . .
C4 C 0.4134(3) 0.38828(14) 0.10838(13) 0.0552(4) Uani 1 1 d . . . . .
C3 C 0.6236(3) 0.36382(14) 0.17210(15) 0.0583(4) Uani 1 1 d . . . . .
H3 H 0.704024 0.291082 0.133352 0.070 Uiso 1 1 calc R U . . .
B1 B 0.6242(2) 0.67359(14) 0.48095(13) 0.0388(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
O2 C7 1.4624(13) . ?
O2 B1 1.3741(16) . ?
O3 C10 1.4293(15) . ?
O3 C9 1.4287(15) . ?
O1 H1 0.832(18) . ?
O1 B1 1.3418(16) . ?
N1 C7 1.4287(14) . ?
N1 C8 1.4595(14) . ?
N1 C11 1.4569(14) . ?
F1 C4 1.3610(15) . ?
C6 C7 1.5072(16) . ?
C6 C1 1.3871(16) . ?
C6 C5 1.3833(16) . ?
C7 H7 0.9800 . ?
C1 C2 1.3943(17) . ?
C1 B1 1.5564(17) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.5074(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.5046(17) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.3835(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.3697(19) . ?
C4 C3 1.372(2) . ?
C3 H3 0.9300 . ?

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
B1 O2 C7 110.22(9) . . ?
C9 O3 C10 110.21(9) . . ?
B1 O1 H1 115.8(12) . . ?
C7 N1 C8 114.65(9) . . ?
C7 N1 C11 113.67(9) . . ?
C11 N1 C8 109.32(9) . . ?
C1 C6 C7 111.17(10) . . ?
C5 C6 C7 126.36(11) . . ?
C5 C6 C1 122.45(11) . . ?
O2 C7 C6 104.89(9) . . ?
O2 C7 H7 108.3 . . ?
N1 C7 O2 113.51(9) . . ?
N1 C7 C6 113.33(9) . . ?
N1 C7 H7 108.3 . . ?
C6 C7 H7 108.3 . . ?
C6 C1 C2 119.21(11) . . ?
C6 C1 B1 104.65(10) . . ?
C2 C1 B1 136.14(11) . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C9 109.18(10) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
N1 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
N1 C11 C10 109.67(10) . . ?
H11A C11 H11B 108.2 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
O3 C10 C11 110.98(10) . . ?
O3 C10 H10A 109.4 . . ?
O3 C10 H10B 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O3 C9 C8 111.53(9) . . ?
O3 C9 H9A 109.3 . . ?
O3 C9 H9B 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.26(12) . . ?
C3 C2 H2 120.4 . . ?
C6 C5 H5 122.0 . . ?
C4 C5 C6 116.06(12) . . ?
C4 C5 H5 122.0 . . ?
F1 C4 C5 118.12(13) . . ?
F1 C4 C3 117.84(13) . . ?
C5 C4 C3 124.03(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.99(12) . . ?
C4 C3 H3 120.5 . . ?
O2 B1 C1 108.97(10) . . ?
O1 B1 O2 123.96(11) . . ?
O1 B1 C1 127.05(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C8 C9 O3 58.31(13) . . . . ?
N1 C11 C10 O3 -58.75(13) . . . . ?
F1 C4 C3 C2 -179.29(12) . . . . ?
C6 C1 C2 C3 -0.05(18) . . . . ?
C6 C1 B1 O2 -1.18(12) . . . . ?
C6 C1 B1 O1 -179.83(12) . . . . ?
C6 C5 C4 F1 179.54(11) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C7 O2 B1 O1 -178.45(11) . . . . ?
C7 O2 B1 C1 2.84(12) . . . . ?
C7 N1 C8 C9 172.52(9) . . . . ?
C7 N1 C11 C10 -171.46(9) . . . . ?
C7 C6 C1 C2 178.78(10) . . . . ?
C7 C6 C1 B1 -0.91(12) . . . . ?
C7 C6 C5 C4 -178.43(11) . . . . ?
C1 C6 C7 O2 2.54(12) . . . . ?
C1 C6 C7 N1 126.89(10) . . . . ?
C1 C6 C5 C4 -0.18(17) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C8 N1 C7 O2 55.12(12) . . . . ?
C8 N1 C7 C6 -64.41(12) . . . . ?
C8 N1 C11 C10 59.03(12) . . . . ?
C11 N1 C7 O2 -71.65(12) . . . . ?
C11 N1 C7 C6 168.82(9) . . . . ?
C11 N1 C8 C9 -58.50(12) . . . . ?
C10 O3 C9 C8 -57.63(13) . . . . ?
C9 O3 C10 C11 57.55(13) . . . . ?
C2 C1 B1 O2 179.21(13) . . . . ?
C2 C1 B1 O1 0.6(2) . . . . ?
C5 C6 C7 O2 -179.04(10) . . . . ?
C5 C6 C7 N1 -54.69(15) . . . . ?
C5 C6 C1 C2 0.30(17) . . . . ?
C5 C6 C1 B1 -179.40(11) . . . . ?
C5 C4 C3 C2 0.4(2) . . . . ?
B1 O2 C7 N1 -127.52(10) . . . . ?
B1 O2 C7 C6 -3.28(11) . . . . ?
B1 C1 C2 C3 179.53(13) . . . . ?

_olex2_date_sample_data_collection 2017-04-14
_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.776
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 molar mixture of dichloromethane and hexane'
