# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_wym-20200924
_database_code_depnum_ccdc_archive 'CCDC 2033909'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D0GC02777D 2020
loop_
_audit_author_name
_audit_author_address
'Wan Yameng'
;Henan Normal University
China
;
_audit_update_record             
;
2020-09-25 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_audit_creation_date             2020-09-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'B F4, C13 H11 N2 O'
_chemical_formula_sum            'C13 H11 B F4 N2 O'
_chemical_formula_weight         298.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1 B1'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.3539(5)
_cell_length_b                   10.9951(6)
_cell_length_c                   11.0590(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1258.98(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2014
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.1500
_cell_measurement_theta_min      3.9270
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4515
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.115
_diffrn_reflns_theta_max         25.115
_diffrn_reflns_theta_min         3.271
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_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     12.00  71.00   1.00    6.01    --   16.13-144.00-147.00   59
  2  ω    -42.00 -17.00   1.00    6.01    --  -16.83  88.00  25.00   25
  3  ω     11.00  82.00   1.00    6.01    --   16.13  57.00  90.00   71
  4  ω     39.00  89.00   1.00    6.01    --   16.13-178.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0349422000
_diffrn_orient_matrix_UB_12      0.0491456000
_diffrn_orient_matrix_UB_13      0.0256366000
_diffrn_orient_matrix_UB_21      -0.0587772000
_diffrn_orient_matrix_UB_22      -0.0311732000
_diffrn_orient_matrix_UB_23      -0.0110560000
_diffrn_orient_matrix_UB_31      0.0042309000
_diffrn_orient_matrix_UB_32      -0.0277764000
_diffrn_orient_matrix_UB_33      0.0577637000
_diffrn_oxdiff_digest_frames     
;
011e637b5571e001d81ace50f91e8b8f63000303fe2
;
_diffrn_oxdiff_digest_hkl        
;
014164ec5542d789307844a326e2cc208b9d64
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.761
_reflns_Friedel_fraction_max     0.761
_reflns_number_gt                1768
_reflns_number_total             1997
_reflns_odcompleteness_completeness 99.60
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 641 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         1997
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      0.870
_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)+(0.1032P)²+0.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1345
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C17(H17), C15(H15), C10(H10), C16(H16), C8(H8), C11(H11), C9(H9)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.2038(3) 0.5103(3) 0.2053(3) 0.0766(10) Uani 1 1 d . . . . .
O20 O 0.6112(3) 0.6166(3) 0.4663(3) 0.0564(9) Uani 1 1 d . . . . .
N7 N 0.5059(3) 0.4567(3) 0.5571(3) 0.0352(7) Uani 1 1 d . . . . .
N19 N 0.4317(3) 0.6602(3) 0.5755(3) 0.0389(8) Uani 1 1 d . . . . .
F3 F 0.3110(3) 0.6471(3) 0.3163(4) 0.0857(11) Uani 1 1 d . . . . .
C18 C 0.3324(4) 0.6210(4) 0.6517(4) 0.0368(9) Uani 1 1 d . . . . .
F4 F 0.3802(3) 0.4569(4) 0.3084(5) 0.1004(13) Uani 1 1 d . . . . .
F5 F 0.1994(6) 0.4985(5) 0.4072(5) 0.1230(18) Uani 1 1 d . . . . .
C13 C 0.3198(4) 0.4975(4) 0.6792(4) 0.0357(9) Uani 1 1 d . . . . .
C12 C 0.4102(3) 0.4111(4) 0.6276(4) 0.0348(8) Uani 1 1 d . . . . .
C14 C 0.2177(4) 0.4591(4) 0.7532(4) 0.0431(10) Uani 1 1 d . . . . .
H14 H 0.207974 0.377027 0.771287 0.052 Uiso 1 1 calc R . . . .
C17 C 0.2462(4) 0.7048(4) 0.7025(4) 0.0445(10) Uani 1 1 d . . . . .
H17 H 0.254978 0.787426 0.686688 0.053 Uiso 1 1 calc R . . . .
C6 C 0.5221(4) 0.5848(4) 0.5281(4) 0.0397(9) Uani 1 1 d . . . . .
C15 C 0.1320(4) 0.5425(4) 0.7990(5) 0.0498(11) Uani 1 1 d . . . . .
H15 H 0.062533 0.516982 0.845886 0.060 Uiso 1 1 calc R . . . .
C10 C 0.4914(4) 0.2099(4) 0.5898(5) 0.0509(12) Uani 1 1 d . . . . .
H10 H 0.485984 0.126168 0.600952 0.061 Uiso 1 1 calc R . . . .
C16 C 0.1498(4) 0.6642(5) 0.7750(4) 0.0514(12) Uani 1 1 d . . . . .
H16 H 0.093805 0.720406 0.809659 0.062 Uiso 1 1 calc R . . . .
C8 C 0.5937(4) 0.3808(4) 0.5021(5) 0.0465(11) Uani 1 1 d . . . . .
H8 H 0.658446 0.413735 0.453851 0.056 Uiso 1 1 calc R . . . .
C21 C 0.4367(4) 0.7880(4) 0.5353(5) 0.0513(12) Uani 1 1 d . . . . .
H21A H 0.354193 0.811129 0.502925 0.077 Uiso 1 1 calc GR . . . .
H21B H 0.501611 0.796763 0.473921 0.077 Uiso 1 1 calc GR . . . .
H21C H 0.457450 0.839345 0.602734 0.077 Uiso 1 1 calc GR . . . .
C11 C 0.4043(4) 0.2868(4) 0.6457(4) 0.0452(10) Uani 1 1 d . . . . .
H11 H 0.340919 0.254616 0.695916 0.054 Uiso 1 1 calc R . . . .
C9 C 0.5869(4) 0.2591(4) 0.5173(5) 0.0496(11) Uani 1 1 d . . . . .
H9 H 0.646222 0.208499 0.479067 0.060 Uiso 1 1 calc R . . . .
B2 B 0.2713(5) 0.5285(5) 0.3096(5) 0.0468(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B2 1.364(6) . ?
O20 C6 1.202(5) . ?
N7 C12 1.357(5) . ?
N7 C6 1.454(5) . ?
N7 C8 1.375(5) . ?
N19 C18 1.397(5) . ?
N19 C6 1.356(5) . ?
N19 C21 1.475(5) . ?
F3 B2 1.369(6) . ?
C18 C13 1.397(5) . ?
C18 C17 1.401(6) . ?
F4 B2 1.375(6) . ?
F5 B2 1.352(7) . ?
C13 C12 1.450(5) . ?
C13 C14 1.402(6) . ?
C12 C11 1.383(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.372(6) . ?
C17 H17 0.9300 . ?
C17 C16 1.356(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(7) . ?
C10 C9 1.383(7) . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.351(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C11 H11 0.9300 . ?
C9 H9 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
C12 N7 C6 124.6(3) . . ?
C12 N7 C8 120.9(3) . . ?
C8 N7 C6 114.4(3) . . ?
C18 N19 C21 120.1(3) . . ?
C6 N19 C18 123.5(3) . . ?
C6 N19 C21 116.2(3) . . ?
N19 C18 C17 120.5(4) . . ?
C13 C18 N19 120.0(3) . . ?
C13 C18 C17 119.5(4) . . ?
C18 C13 C12 119.4(4) . . ?
C18 C13 C14 119.3(4) . . ?
C14 C13 C12 121.3(4) . . ?
N7 C12 C13 117.1(3) . . ?
N7 C12 C11 118.7(4) . . ?
C11 C12 C13 124.2(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C18 C17 H17 120.3 . . ?
C16 C17 C18 119.3(4) . . ?
C16 C17 H17 120.3 . . ?
O20 C6 N7 119.8(4) . . ?
O20 C6 N19 124.9(4) . . ?
N19 C6 N7 115.3(3) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.5(4) . . ?
C16 C15 H15 120.3 . . ?
C11 C10 H10 120.5 . . ?
C11 C10 C9 119.1(4) . . ?
C9 C10 H10 120.5 . . ?
C17 C16 C15 122.2(4) . . ?
C17 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
N7 C8 H8 119.6 . . ?
C9 C8 N7 120.7(4) . . ?
C9 C8 H8 119.6 . . ?
N19 C21 H21A 109.5 . . ?
N19 C21 H21B 109.5 . . ?
N19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.8(4) . . ?
C8 C9 H9 120.1 . . ?
F1 B2 F3 109.8(4) . . ?
F1 B2 F4 109.1(5) . . ?
F3 B2 F4 107.5(4) . . ?
F5 B2 F1 110.9(4) . . ?
F5 B2 F3 110.8(5) . . ?
F5 B2 F4 108.6(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 C12 C11 C10 -2.1(6) . . . . ?
N7 C8 C9 C10 -0.6(7) . . . . ?
N19 C18 C13 C12 -0.2(6) . . . . ?
N19 C18 C13 C14 -178.3(4) . . . . ?
N19 C18 C17 C16 179.2(4) . . . . ?
C18 N19 C6 O20 -177.0(4) . . . . ?
C18 N19 C6 N7 2.9(6) . . . . ?
C18 C13 C12 N7 1.9(5) . . . . ?
C18 C13 C12 C11 -177.9(4) . . . . ?
C18 C13 C14 C15 -0.7(6) . . . . ?
C18 C17 C16 C15 -1.2(7) . . . . ?
C13 C18 C17 C16 -1.7(6) . . . . ?
C13 C12 C11 C10 177.7(4) . . . . ?
C13 C14 C15 C16 -2.2(7) . . . . ?
C12 N7 C6 O20 178.8(4) . . . . ?
C12 N7 C6 N19 -1.1(6) . . . . ?
C12 N7 C8 C9 -0.2(6) . . . . ?
C12 C13 C14 C15 -178.8(4) . . . . ?
C14 C13 C12 N7 180.0(4) . . . . ?
C14 C13 C12 C11 0.2(6) . . . . ?
C14 C15 C16 C17 3.1(7) . . . . ?
C17 C18 C13 C12 -179.2(4) . . . . ?
C17 C18 C13 C14 2.6(6) . . . . ?
C6 N7 C12 C13 -1.3(5) . . . . ?
C6 N7 C12 C11 178.5(4) . . . . ?
C6 N7 C8 C9 -177.5(4) . . . . ?
C6 N19 C18 C13 -2.3(6) . . . . ?
C6 N19 C18 C17 176.7(4) . . . . ?
C8 N7 C12 C13 -178.3(4) . . . . ?
C8 N7 C12 C11 1.5(6) . . . . ?
C8 N7 C6 O20 -4.0(6) . . . . ?
C8 N7 C6 N19 176.1(4) . . . . ?
C21 N19 C18 C13 173.1(4) . . . . ?
C21 N19 C18 C17 -7.9(6) . . . . ?
C21 N19 C6 O20 7.4(6) . . . . ?
C21 N19 C6 N7 -172.7(3) . . . . ?
C11 C10 C9 C8 0.0(7) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?

_olex2_date_sample_data_collection 2020-09-24
_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.551
