# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_ni1cult
_database_code_depnum_ccdc_archive 'CCDC 1832353'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 B F2 N3 O'
_chemical_formula_sum            'C16 H16 B F2 N3 O'
_chemical_formula_weight         315.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   7.4604(4)
_cell_length_b                   9.2599(4)
_cell_length_c                   11.5405(6)
_cell_angle_alpha                86.303(4)
_cell_angle_beta                 81.372(4)
_cell_angle_gamma                72.383(4)
_cell_volume                     751.10(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3105
_cell_measurement_temperature    220.01(10)
_cell_measurement_theta_max      75.4520
_cell_measurement_theta_min      3.8620
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83090
_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            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0084
_diffrn_reflns_av_unetI/netI     0.0107
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3919
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.974
_diffrn_reflns_theta_min         3.875
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.963
_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    -24.00  71.00   1.00    2.00    --   40.45 -80.00 -75.00   95
  2  ω     72.00 117.00   1.00    3.00    --  110.57-125.00-150.00   45
  3  ω     85.00 121.00   1.00    3.00    --  110.57-125.00   0.00   36
  4  ω     61.00 141.00   1.00    3.00    --  110.57 -61.00 150.00   80
  5  ω     81.00 176.00   1.00    3.00    --  110.57  30.00 150.00   95
  6  ω    145.00 176.00   1.00    3.00    --  110.57 125.00  60.00   31
  7  ω    102.00 128.00   1.00    3.00    --  110.57 125.00  60.00   26
  8  ω     80.00 178.00   1.00    3.00    --  110.57  30.00-120.00   98
  9  ω    117.00 178.00   1.00    3.00    --  110.57 125.00-180.00   61
 10  ω     36.00 134.00   1.00    3.00    --  110.57 -45.00 -90.00   98
 11  ω     39.00 140.00   1.00    3.00    --  110.57 -61.00  60.00  101
 12  ω   -108.00 -11.00   1.00    2.00    --  -40.45 -57.00  30.00   97
 13  ω   -114.00 -11.00   1.00    2.00    --  -40.45 -57.00 150.00  103
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0674253000
_diffrn_orient_matrix_UB_12      -0.0338054000
_diffrn_orient_matrix_UB_13      -0.1122832000
_diffrn_orient_matrix_UB_21      0.0730559000
_diffrn_orient_matrix_UB_22      -0.1711909000
_diffrn_orient_matrix_UB_23      0.0272931000
_diffrn_orient_matrix_UB_31      -0.1948317000
_diffrn_orient_matrix_UB_32      0.0057102000
_diffrn_orient_matrix_UB_33      0.0698959000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2448
_reflns_number_total             2569
_reflns_odcompleteness_completeness 98.14
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.128
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2569
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.007
_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)+(0.0430P)²+0.1630P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0798
_refine_ls_wR_factor_ref         0.0807
_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:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 0.26979(13) 0.66033(9) 0.11511(6) 0.0590(2) Uani 1 1 d . . . . .
F2 F 0.51970(12) 0.70894(9) 0.17549(8) 0.0626(3) Uani 1 1 d . . . . .
O1 O 0.25078(12) 0.71639(9) 0.31398(7) 0.0397(2) Uani 1 1 d . . . . .
N1 N 0.44363(13) 0.48108(10) 0.25358(8) 0.0316(2) Uani 1 1 d . . . . .
N2 N 0.36841(13) 0.47049(10) 0.37031(8) 0.0308(2) Uani 1 1 d . . . . .
N3 N -0.17590(14) 0.77148(11) 0.83700(8) 0.0386(2) Uani 1 1 d . . . . .
C1 C 0.55701(15) 0.36784(12) 0.19422(9) 0.0329(2) Uani 1 1 d . . . . .
H1 H 0.5975 0.3918 0.1162 0.039 Uiso 1 1 calc R . . . .
C2 C 0.63216(15) 0.21000(12) 0.22793(9) 0.0306(2) Uani 1 1 d . . . . .
C3 C 0.75373(16) 0.11635(13) 0.14018(10) 0.0359(3) Uani 1 1 d . . . . .
H3 H 0.7813 0.1577 0.0655 0.043 Uiso 1 1 calc R . . . .
C4 C 0.83345(16) -0.03639(13) 0.16258(11) 0.0397(3) Uani 1 1 d . . . . .
H4 H 0.9160 -0.0983 0.1035 0.048 Uiso 1 1 calc R . . . .
C5 C 0.79174(17) -0.09775(13) 0.27158(11) 0.0415(3) Uani 1 1 d . . . . .
H5 H 0.8450 -0.2018 0.2868 0.050 Uiso 1 1 calc R . . . .
C6 C 0.67109(18) -0.00590(14) 0.35886(11) 0.0424(3) Uani 1 1 d . . . . .
H6 H 0.6429 -0.0484 0.4330 0.051 Uiso 1 1 calc R . . . .
C7 C 0.59198(16) 0.14704(13) 0.33821(10) 0.0356(3) Uani 1 1 d . . . . .
H7 H 0.5114 0.2085 0.3982 0.043 Uiso 1 1 calc R . . . .
C10 C 0.26112(15) 0.60814(12) 0.39657(9) 0.0303(2) Uani 1 1 d . . . . .
C11 C 0.15106(15) 0.64764(12) 0.51019(9) 0.0299(2) Uani 1 1 d . . . . .
C12 C 0.03065(16) 0.79469(12) 0.53000(10) 0.0328(2) Uani 1 1 d . . . . .
H12 H 0.0233 0.8673 0.4687 0.039 Uiso 1 1 calc R . . . .
C13 C -0.07716(16) 0.83596(12) 0.63661(10) 0.0331(2) Uani 1 1 d . . . . .
H13 H -0.1573 0.9358 0.6469 0.040 Uiso 1 1 calc R . . . .
C14 C -0.06931(15) 0.73071(12) 0.73082(9) 0.0307(2) Uani 1 1 d . . . . .
C15 C 0.05364(16) 0.58171(12) 0.71050(10) 0.0346(3) Uani 1 1 d . . . . .
H15 H 0.0627 0.5087 0.7716 0.042 Uiso 1 1 calc R . . . .
C16 C 0.15950(16) 0.54238(12) 0.60321(10) 0.0331(2) Uani 1 1 d . . . . .
H16 H 0.2393 0.4427 0.5920 0.040 Uiso 1 1 calc R . . . .
C17 C -0.28362(17) 0.92881(14) 0.85911(11) 0.0404(3) Uani 1 1 d . . . . .
H17A H -0.1974 0.9901 0.8517 0.061 Uiso 1 1 calc GR . . . .
H17B H -0.3529 0.9371 0.9377 0.061 Uiso 1 1 calc GR . . . .
H17C H -0.3724 0.9642 0.8027 0.061 Uiso 1 1 calc GR . . . .
C18 C -0.1514(2) 0.66785(15) 0.93650(11) 0.0476(3) Uani 1 1 d . . . . .
H18A H -0.1672 0.5727 0.9165 0.071 Uiso 1 1 calc GR . . . .
H18B H -0.2453 0.7114 1.0024 0.071 Uiso 1 1 calc GR . . . .
H18C H -0.0251 0.6499 0.9574 0.071 Uiso 1 1 calc GR . . . .
B1 B 0.3715(2) 0.65101(15) 0.20703(12) 0.0394(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
F1 B1 1.3781(17) . ?
F2 B1 1.3621(17) . ?
O1 C10 1.3308(13) . ?
O1 B1 1.4609(15) . ?
N1 N2 1.3888(13) . ?
N1 C1 1.2909(14) . ?
N1 B1 1.5872(16) . ?
N2 C10 1.3102(14) . ?
N3 C14 1.3646(14) . ?
N3 C17 1.4530(15) . ?
N3 C18 1.4448(16) . ?
C1 C2 1.4485(16) . ?
C2 C3 1.4006(15) . ?
C2 C7 1.3947(16) . ?
C3 C4 1.3823(17) . ?
C4 C5 1.3783(18) . ?
C5 C6 1.3868(17) . ?
C6 C7 1.3796(17) . ?
C10 C11 1.4437(15) . ?
C11 C12 1.3970(15) . ?
C11 C16 1.3980(16) . ?
C12 C13 1.3727(16) . ?
C13 C14 1.4083(16) . ?
C14 C15 1.4182(15) . ?
C15 C16 1.3711(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 B1 108.92(9) . . ?
N2 N1 B1 109.91(8) . . ?
C1 N1 N2 123.90(9) . . ?
C1 N1 B1 126.18(10) . . ?
C10 N2 N1 104.68(9) . . ?
C14 N3 C17 120.37(10) . . ?
C14 N3 C18 120.47(10) . . ?
C18 N3 C17 117.75(10) . . ?
N1 C1 C2 130.66(10) . . ?
C3 C2 C1 115.55(10) . . ?
C7 C2 C1 125.32(10) . . ?
C7 C2 C3 119.13(10) . . ?
C4 C3 C2 120.50(11) . . ?
C5 C4 C3 119.93(11) . . ?
C4 C5 C6 119.94(11) . . ?
C7 C6 C5 120.81(12) . . ?
C6 C7 C2 119.70(10) . . ?
O1 C10 C11 118.37(9) . . ?
N2 C10 O1 118.43(10) . . ?
N2 C10 C11 123.19(10) . . ?
C12 C11 C10 120.16(10) . . ?
C12 C11 C16 117.77(10) . . ?
C16 C11 C10 122.07(10) . . ?
C13 C12 C11 121.75(10) . . ?
C12 C13 C14 120.85(10) . . ?
N3 C14 C13 120.99(10) . . ?
N3 C14 C15 121.77(10) . . ?
C13 C14 C15 117.23(10) . . ?
C16 C15 C14 121.08(10) . . ?
C15 C16 C11 121.31(10) . . ?
F1 B1 O1 112.42(11) . . ?
F1 B1 N1 110.74(10) . . ?
F2 B1 F1 111.05(11) . . ?
F2 B1 O1 113.13(11) . . ?
F2 B1 N1 110.83(10) . . ?
O1 B1 N1 98.03(9) . . ?

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
O1 C10 C11 C12 2.88(16) . . . . ?
O1 C10 C11 C16 -177.40(10) . . . . ?
N1 N2 C10 O1 -0.50(13) . . . . ?
N1 N2 C10 C11 178.45(9) . . . . ?
N1 C1 C2 C3 -179.91(11) . . . . ?
N1 C1 C2 C7 0.44(19) . . . . ?
N2 N1 C1 C2 0.42(18) . . . . ?
N2 N1 B1 F1 -119.27(10) . . . . ?
N2 N1 B1 F2 117.02(11) . . . . ?
N2 N1 B1 O1 -1.55(12) . . . . ?
N2 C10 C11 C12 -176.07(10) . . . . ?
N2 C10 C11 C16 3.66(17) . . . . ?
N3 C14 C15 C16 179.84(10) . . . . ?
C1 N1 N2 C10 -179.47(10) . . . . ?
C1 N1 B1 F1 61.52(15) . . . . ?
C1 N1 B1 F2 -62.20(15) . . . . ?
C1 N1 B1 O1 179.24(10) . . . . ?
C1 C2 C3 C4 -179.89(10) . . . . ?
C1 C2 C7 C6 179.20(11) . . . . ?
C2 C3 C4 C5 0.70(18) . . . . ?
C3 C2 C7 C6 -0.44(17) . . . . ?
C3 C4 C5 C6 -0.52(18) . . . . ?
C4 C5 C6 C7 -0.15(19) . . . . ?
C5 C6 C7 C2 0.63(18) . . . . ?
C7 C2 C3 C4 -0.22(17) . . . . ?
C10 O1 B1 F1 117.64(11) . . . . ?
C10 O1 B1 F2 -115.58(11) . . . . ?
C10 O1 B1 N1 1.21(12) . . . . ?
C10 C11 C12 C13 179.49(10) . . . . ?
C10 C11 C16 C15 -179.84(10) . . . . ?
C11 C12 C13 C14 0.35(17) . . . . ?
C12 C11 C16 C15 -0.11(16) . . . . ?
C12 C13 C14 N3 179.82(10) . . . . ?
C12 C13 C14 C15 -0.09(16) . . . . ?
C13 C14 C15 C16 -0.25(16) . . . . ?
C14 C15 C16 C11 0.36(17) . . . . ?
C16 C11 C12 C13 -0.25(16) . . . . ?
C17 N3 C14 C13 -6.99(16) . . . . ?
C17 N3 C14 C15 172.92(10) . . . . ?
C18 N3 C14 C13 -173.15(11) . . . . ?
C18 N3 C14 C15 6.76(17) . . . . ?
B1 O1 C10 N2 -0.59(14) . . . . ?
B1 O1 C10 C11 -179.59(10) . . . . ?
B1 N1 N2 C10 1.30(11) . . . . ?
B1 N1 C1 C2 179.53(11) . . . . ?

_olex2_date_sample_data_collection 2017-04-10
_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 1.567
_oxdiff_exptl_absorpt_empirical_full_min 0.685
####################################################################### 
# 
# 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_exp_4122
_database_code_depnum_ccdc_archive 'CCDC 1832354'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-05-28 downloaded from the CCDC.
;
_audit_creation_date             2017-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 B F2 N3 O'
_chemical_formula_sum            'C16 H16 B F2 N3 O'
_chemical_formula_weight         315.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.4912(16)
_cell_length_b                   17.4789(16)
_cell_length_c                   10.2389(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.403(15)
_cell_angle_gamma                90
_cell_volume                     1592.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1066
_cell_measurement_temperature    297
_cell_measurement_theta_max      22.2020
_cell_measurement_theta_min      3.1430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.597
_exptl_crystal_size_mid          0.479
_exptl_crystal_size_min          0.304
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            6453
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         3.153
_diffrn_ambient_temperature      297
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_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    -12.00  65.00   1.00   10.00    --   16.81  19.00-120.00   77
  2  ω    -36.00  63.00   1.00   10.00    --   16.81   0.00-180.00   99
  3  ω    -13.00  17.00   1.00   10.00    --  -17.43 -99.00  60.00   30
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0767398000
_diffrn_orient_matrix_UB_12      0.0072953000
_diffrn_orient_matrix_UB_13      0.0386520000
_diffrn_orient_matrix_UB_21      0.0057894000
_diffrn_orient_matrix_UB_22      0.0219923000
_diffrn_orient_matrix_UB_23      -0.0561611000
_diffrn_orient_matrix_UB_31      -0.0205853000
_diffrn_orient_matrix_UB_32      0.0333240000
_diffrn_orient_matrix_UB_33      0.0286497000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1765
_reflns_number_total             3279
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.208
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1189
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.015
_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)+(0.0578P)²+0.1061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1177
_refine_ls_wR_factor_ref         0.1484
_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:
 C16(H16), C9(H9), C7(H7), C15(H15), C5(H5), C4(H4), C14(H14), C12(H12),
 C8(H8), C13(H13)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_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 0.8624(2) 0.53020(9) 1.11540(17) 0.1025(7) Uani 1 1 d . . . . .
F2 F 1.04850(19) 0.59755(9) 1.08524(18) 0.1006(6) Uani 1 1 d . . . . .
O1 O 0.8575(2) 0.66419(9) 1.13480(16) 0.0743(6) Uani 1 1 d . . . . .
N3 N 0.7979(2) 0.61393(10) 0.91417(19) 0.0526(5) Uani 1 1 d . . . . .
N2 N 0.7188(2) 0.68202(10) 0.90856(19) 0.0519(5) Uani 1 1 d . . . . .
C10 C 0.7587(3) 0.70530(12) 1.0362(2) 0.0498(6) Uani 1 1 d . . . . .
C11 C 0.6987(3) 0.77493(12) 1.0752(2) 0.0488(6) Uani 1 1 d . . . . .
C16 C 0.5978(3) 0.81892(12) 0.9733(2) 0.0539(6) Uani 1 1 d . . . . .
H16 H 0.570553 0.804674 0.880198 0.065 Uiso 1 1 calc R . . . .
C6 C 0.6955(3) 0.58813(13) 0.6605(2) 0.0550(6) Uani 1 1 d . . . . .
C9 C 0.7820(3) 0.57439(13) 0.8022(3) 0.0575(6) Uani 1 1 d . . . . .
H9 H 0.837175 0.529202 0.818051 0.069 Uiso 1 1 calc R . . . .
N1 N 0.4753(3) 0.62030(15) 0.2309(2) 0.0875(8) Uani 1 1 d . . . . .
C7 C 0.6068(3) 0.65275(14) 0.6068(3) 0.0656(7) Uani 1 1 d . . . . .
H7 H 0.597060 0.689993 0.667966 0.079 Uiso 1 1 calc R . . . .
C15 C 0.5373(3) 0.88357(13) 1.0085(3) 0.0651(7) Uani 1 1 d . . . . .
H15 H 0.468698 0.912788 0.939359 0.078 Uiso 1 1 calc R . . . .
C5 C 0.7040(3) 0.53389(14) 0.5620(3) 0.0649(7) Uani 1 1 d . . . . .
H5 H 0.760357 0.489744 0.593410 0.078 Uiso 1 1 calc R . . . .
C4 C 0.6329(3) 0.54361(16) 0.4224(3) 0.0702(8) Uani 1 1 d . . . . .
H4 H 0.641901 0.506201 0.361220 0.084 Uiso 1 1 calc R . . . .
C14 C 0.5778(3) 0.90530(14) 1.1455(3) 0.0704(8) Uani 1 1 d . . . . .
H14 H 0.536811 0.949196 1.169220 0.084 Uiso 1 1 calc R . . . .
C3 C 0.5466(3) 0.60871(16) 0.3695(3) 0.0670(7) Uani 1 1 d . . . . .
C12 C 0.7387(3) 0.79714(16) 1.2129(3) 0.0758(8) Uani 1 1 d . . . . .
H12 H 0.806479 0.767974 1.282809 0.091 Uiso 1 1 calc R . . . .
C8 C 0.5346(3) 0.66244(15) 0.4673(3) 0.0733(8) Uani 1 1 d . . . . .
H8 H 0.475726 0.705803 0.435857 0.088 Uiso 1 1 calc R . . . .
C13 C 0.6779(3) 0.86247(17) 1.2464(3) 0.0835(9) Uani 1 1 d . . . . .
H13 H 0.705721 0.877508 1.339063 0.100 Uiso 1 1 calc R . . . .
C2 C 0.3806(4) 0.6863(2) 0.1777(3) 0.0992(11) Uani 1 1 d . . . . .
H2A H 0.293638 0.683415 0.204833 0.149 Uiso 1 1 calc GR . . . .
H2B H 0.349612 0.687189 0.077883 0.149 Uiso 1 1 calc GR . . . .
H2C H 0.435852 0.732081 0.215095 0.149 Uiso 1 1 calc GR . . . .
B1 B 0.9000(4) 0.59732(17) 1.0689(3) 0.0660(9) Uani 1 1 d . . . . .
C1 C 0.4917(4) 0.5664(2) 0.1289(3) 0.1128(12) Uani 1 1 d . . . . .
H1A H 0.595785 0.553279 0.152295 0.169 Uiso 1 1 calc GR . . . .
H1B H 0.455205 0.589293 0.037983 0.169 Uiso 1 1 calc GR . . . .
H1C H 0.434731 0.521009 0.129028 0.169 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.359(3) . ?
F2 B1 1.361(4) . ?
O1 C10 1.324(2) . ?
O1 B1 1.474(3) . ?
N3 N2 1.398(2) . ?
N3 C9 1.301(3) . ?
N3 B1 1.570(3) . ?
N2 C10 1.293(3) . ?
C10 C11 1.457(3) . ?
C11 C16 1.379(3) . ?
C11 C12 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.371(3) . ?
C6 C9 1.417(3) . ?
C6 C7 1.401(3) . ?
C6 C5 1.407(3) . ?
C9 H9 0.9300 . ?
N1 C3 1.358(3) . ?
N1 C2 1.447(4) . ?
N1 C1 1.455(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.363(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.362(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.396(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.359(4) . ?
C3 C8 1.406(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C8 H8 0.9300 . ?
C13 H13 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 B1 108.39(19) . . ?
N2 N3 B1 109.43(17) . . ?
C9 N3 N2 121.36(19) . . ?
C9 N3 B1 129.2(2) . . ?
C10 N2 N3 105.22(17) . . ?
O1 C10 C11 119.0(2) . . ?
N2 C10 O1 118.7(2) . . ?
N2 C10 C11 122.3(2) . . ?
C16 C11 C10 119.5(2) . . ?
C16 C11 C12 119.1(2) . . ?
C12 C11 C10 121.3(2) . . ?
C11 C16 H16 119.9 . . ?
C15 C16 C11 120.3(2) . . ?
C15 C16 H16 119.9 . . ?
C7 C6 C9 126.4(2) . . ?
C7 C6 C5 116.0(2) . . ?
C5 C6 C9 117.5(2) . . ?
N3 C9 C6 131.3(2) . . ?
N3 C9 H9 114.4 . . ?
C6 C9 H9 114.4 . . ?
C3 N1 C2 122.0(2) . . ?
C3 N1 C1 121.0(3) . . ?
C2 N1 C1 117.0(3) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 H7 119.1 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.2(2) . . ?
C14 C15 H15 119.9 . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
N1 C3 C4 122.6(2) . . ?
N1 C3 C8 120.7(3) . . ?
C4 C3 C8 116.7(2) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12 120.1 . . ?
C7 C8 C3 121.8(3) . . ?
C7 C8 H8 119.1 . . ?
C3 C8 H8 119.1 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
F1 B1 F2 110.3(2) . . ?
F1 B1 O1 112.2(3) . . ?
F1 B1 N3 111.6(2) . . ?
F2 B1 O1 112.2(2) . . ?
F2 B1 N3 111.8(2) . . ?
O1 B1 N3 98.30(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

_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 1.082
_oxdiff_exptl_absorpt_empirical_full_min 0.935
