# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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. 
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data_eg080
_database_code_depnum_ccdc_archive 'CCDC 1995215'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H22 B N O2'
_chemical_formula_sum            'C14 H22 B N O2'
_chemical_formula_weight         247.13
_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'
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   17.0129(10)
_cell_length_b                   12.3612(7)
_cell_length_c                   27.5884(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5801.8(6)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9925
_cell_measurement_temperature    120
_cell_measurement_theta_max      30.505
_cell_measurement_theta_min      2.166
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6317
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1519 before and 0.0504 after correction. The Ratio of minimum to maximum transmission is 0.8467. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.132
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2144
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            70012
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.624
_diffrn_reflns_theta_min         1.476
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6565
_reflns_number_total             8906
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.465
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     337
_refine_ls_number_reflns         8906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.089
_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)+(0.0649P)²+3.7797P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1640
_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:
 C3A(H3A), C6A(H6A), C3(H3), C6(H6), C4A(H4A), C5A(H5A), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC), C11A(H11A,H11B,H11C), C12A(H12A,H12B,
 H12C), C7A(H7AA,H7AB,H7AC), C7(H7A,H7B,H7C), C12(H12D,H12E,H12F), C14A(H14A,
 H14B,H14C), C13A(H13A,H13B,H13C), C11(H11D,H11E,H11F), C14(H14D,H14E,H14F),
 C13(H13D,H13E,H13F)
;
_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
O1A O 0.31506(6) 0.43436(9) 0.51292(4) 0.0227(2) Uani 1 1 d . . . . .
O1 O 0.54362(6) 0.59170(9) 0.29839(4) 0.0231(2) Uani 1 1 d . . . . .
O2A O 0.33557(6) 0.46902(9) 0.43258(4) 0.0257(2) Uani 1 1 d . . . . .
O2 O 0.55199(6) 0.55673(10) 0.21727(4) 0.0259(2) Uani 1 1 d . . . . .
N1A N 0.44840(8) 0.29587(11) 0.55278(4) 0.0243(3) Uani 1 1 d . . . . .
N1 N 0.69775(8) 0.67681(11) 0.33667(4) 0.0241(3) Uani 1 1 d . . . . .
C2 C 0.66153(8) 0.67643(11) 0.25083(5) 0.0180(3) Uani 1 1 d . . . . .
C2A C 0.41839(8) 0.31515(12) 0.46654(5) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.70844(8) 0.71677(12) 0.28950(5) 0.0188(3) Uani 1 1 d . . . . .
C1A C 0.45682(8) 0.25960(12) 0.50487(5) 0.0192(3) Uani 1 1 d . . . . .
C3A C 0.42944(8) 0.27795(13) 0.41914(5) 0.0225(3) Uani 1 1 d . . . . .
H3A H 0.4058 0.3168 0.3932 0.027 Uiso 1 1 calc R . . . .
C6A C 0.50078(9) 0.16639(13) 0.49371(6) 0.0244(3) Uani 1 1 d . . . . .
H6A H 0.5257 0.1274 0.5191 0.029 Uiso 1 1 calc R . . . .
C3 C 0.67672(9) 0.71471(12) 0.20399(5) 0.0228(3) Uani 1 1 d . . . . .
H3 H 0.6476 0.6854 0.1777 0.027 Uiso 1 1 calc R . . . .
C6 C 0.76368(9) 0.79828(13) 0.27960(6) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.7940 0.8276 0.3054 0.030 Uiso 1 1 calc R . . . .
C9 C 0.48111(8) 0.51389(13) 0.28810(5) 0.0233(3) Uani 1 1 d . . . . .
C4A C 0.47373(9) 0.18620(14) 0.40836(6) 0.0284(3) Uani 1 1 d . . . . .
H4A H 0.4800 0.1624 0.3758 0.034 Uiso 1 1 calc R . . . .
C9A C 0.27190(8) 0.53408(13) 0.50240(5) 0.0228(3) Uani 1 1 d . . . . .
C10A C 0.26614(9) 0.53209(13) 0.44600(5) 0.0254(3) Uani 1 1 d . . . . .
C10 C 0.47416(9) 0.51943(13) 0.23211(5) 0.0239(3) Uani 1 1 d . . . . .
C8 C 0.70601(9) 0.56061(14) 0.34336(6) 0.0281(3) Uani 1 1 d . . . . .
H8A H 0.6863 0.5229 0.3146 0.042 Uiso 1 1 calc GR . . . .
H8B H 0.6757 0.5379 0.3718 0.042 Uiso 1 1 calc GR . . . .
H8C H 0.7616 0.5427 0.3482 0.042 Uiso 1 1 calc GR . . . .
C5A C 0.50843(9) 0.13061(14) 0.44639(6) 0.0284(3) Uani 1 1 d . . . . .
H5A H 0.5379 0.0670 0.4399 0.034 Uiso 1 1 calc R . . . .
C4 C 0.73267(9) 0.79383(14) 0.19446(6) 0.0284(3) Uani 1 1 d . . . . .
H4 H 0.7418 0.8179 0.1623 0.034 Uiso 1 1 calc R . . . .
C8A C 0.47274(9) 0.40701(14) 0.56303(6) 0.0284(3) Uani 1 1 d . . . . .
H8AA H 0.5295 0.4089 0.5689 0.043 Uiso 1 1 calc GR . . . .
H8AB H 0.4449 0.4335 0.5918 0.043 Uiso 1 1 calc GR . . . .
H8AC H 0.4601 0.4532 0.5352 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.77488(9) 0.83686(14) 0.23286(6) 0.0291(3) Uani 1 1 d . . . . .
H5 H 0.8117 0.8932 0.2271 0.035 Uiso 1 1 calc R . . . .
C11A C 0.19334(10) 0.52912(16) 0.52852(6) 0.0336(4) Uani 1 1 d . . . . .
H11A H 0.1651 0.4637 0.5187 0.050 Uiso 1 1 calc GR . . . .
H11B H 0.1621 0.5930 0.5201 0.050 Uiso 1 1 calc GR . . . .
H11C H 0.2022 0.5275 0.5636 0.050 Uiso 1 1 calc GR . . . .
C12A C 0.32161(11) 0.62680(15) 0.52205(7) 0.0359(4) Uani 1 1 d . . . . .
H12A H 0.3312 0.6156 0.5567 0.054 Uiso 1 1 calc GR . . . .
H12B H 0.2937 0.6953 0.5173 0.054 Uiso 1 1 calc GR . . . .
H12C H 0.3719 0.6291 0.5048 0.054 Uiso 1 1 calc GR . . . .
C7A C 0.47280(11) 0.22339(16) 0.59155(6) 0.0357(4) Uani 1 1 d . . . . .
H7AA H 0.4497 0.1517 0.5863 0.054 Uiso 1 1 calc GR . . . .
H7AB H 0.4549 0.2522 0.6228 0.054 Uiso 1 1 calc GR . . . .
H7AC H 0.5302 0.2175 0.5917 0.054 Uiso 1 1 calc GR . . . .
B1A B 0.35656(9) 0.40767(14) 0.47204(6) 0.0189(3) Uani 1 1 d . . . . .
C7 C 0.73362(11) 0.73631(17) 0.37650(6) 0.0373(4) Uani 1 1 d . . . . .
H7A H 0.7907 0.7253 0.3760 0.056 Uiso 1 1 calc GR . . . .
H7B H 0.7123 0.7101 0.4073 0.056 Uiso 1 1 calc GR . . . .
H7C H 0.7220 0.8136 0.3730 0.056 Uiso 1 1 calc GR . . . .
C12 C 0.40800(10) 0.54369(17) 0.31615(7) 0.0363(4) Uani 1 1 d . . . . .
H12D H 0.4176 0.5338 0.3509 0.054 Uiso 1 1 calc GR . . . .
H12E H 0.3644 0.4971 0.3060 0.054 Uiso 1 1 calc GR . . . .
H12F H 0.3946 0.6195 0.3098 0.054 Uiso 1 1 calc GR . . . .
C14A C 0.27184(12) 0.64205(16) 0.42160(7) 0.0407(5) Uani 1 1 d . . . . .
H14A H 0.3218 0.6763 0.4303 0.061 Uiso 1 1 calc GR . . . .
H14B H 0.2282 0.6878 0.4324 0.061 Uiso 1 1 calc GR . . . .
H14C H 0.2692 0.6329 0.3863 0.061 Uiso 1 1 calc GR . . . .
B1 B 0.58594(9) 0.60612(13) 0.25677(5) 0.0182(3) Uani 1 1 d . . . . .
C13A C 0.19468(11) 0.47029(17) 0.42728(7) 0.0388(4) Uani 1 1 d . . . . .
H13A H 0.1988 0.4617 0.3921 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.1468 0.5106 0.4351 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.1926 0.3988 0.4426 0.058 Uiso 1 1 calc GR . . . .
C11 C 0.51257(11) 0.40421(16) 0.30582(7) 0.0381(4) Uani 1 1 d . . . . .
H11D H 0.5595 0.3847 0.2872 0.057 Uiso 1 1 calc GR . . . .
H11E H 0.4721 0.3487 0.3013 0.057 Uiso 1 1 calc GR . . . .
H11F H 0.5261 0.4093 0.3403 0.057 Uiso 1 1 calc GR . . . .
C14 C 0.41646(11) 0.60780(18) 0.21626(7) 0.0416(5) Uani 1 1 d . . . . .
H14D H 0.4297 0.6758 0.2326 0.062 Uiso 1 1 calc GR . . . .
H14E H 0.3628 0.5863 0.2250 0.062 Uiso 1 1 calc GR . . . .
H14F H 0.4199 0.6177 0.1811 0.062 Uiso 1 1 calc GR . . . .
C13 C 0.45562(13) 0.41437(18) 0.20711(7) 0.0462(5) Uani 1 1 d . . . . .
H13D H 0.4507 0.4268 0.1722 0.069 Uiso 1 1 calc GR . . . .
H13E H 0.4060 0.3854 0.2197 0.069 Uiso 1 1 calc GR . . . .
H13F H 0.4980 0.3624 0.2132 0.069 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
O1A C9A 1.4638(18) . ?
O1A B1A 1.3709(18) . ?
O1 C9 1.4618(17) . ?
O1 B1 1.3670(18) . ?
O2A C10A 1.4630(17) . ?
O2A B1A 1.3740(19) . ?
O2 C10 1.4606(17) . ?
O2 B1 1.3762(18) . ?
N1A C1A 1.4029(18) . ?
N1A C8A 1.462(2) . ?
N1A C7A 1.456(2) . ?
N1 C1 1.4038(19) . ?
N1 C8 1.455(2) . ?
N1 C7 1.456(2) . ?
C2 C1 1.4227(19) . ?
C2 C3 1.400(2) . ?
C2 B1 1.561(2) . ?
C2A C1A 1.4204(19) . ?
C2A C3A 1.3990(19) . ?
C2A B1A 1.561(2) . ?
C1 C6 1.405(2) . ?
C1A C6A 1.408(2) . ?
C3A C4A 1.394(2) . ?
C6A C5A 1.385(2) . ?
C3 C4 1.390(2) . ?
C6 C5 1.388(2) . ?
C9 C10 1.551(2) . ?
C9 C12 1.510(2) . ?
C9 C11 1.537(2) . ?
C4A C5A 1.386(2) . ?
C9A C10A 1.559(2) . ?
C9A C11A 1.520(2) . ?
C9A C12A 1.524(2) . ?
C10A C14A 1.520(2) . ?
C10A C13A 1.526(3) . ?
C10 C14 1.532(3) . ?
C10 C13 1.504(2) . ?
C4 C5 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1A O1A C9A 107.34(11) . . ?
B1 O1 C9 107.81(11) . . ?
B1A O2A C10A 107.66(11) . . ?
B1 O2 C10 107.37(11) . . ?
C1A N1A C8A 116.97(12) . . ?
C1A N1A C7A 117.80(14) . . ?
C7A N1A C8A 110.81(13) . . ?
C1 N1 C8 116.91(12) . . ?
C1 N1 C7 117.88(13) . . ?
C8 N1 C7 111.24(14) . . ?
C1 C2 B1 125.36(12) . . ?
C3 C2 C1 118.04(13) . . ?
C3 C2 B1 115.93(12) . . ?
C1A C2A B1A 126.30(12) . . ?
C3A C2A C1A 118.37(13) . . ?
C3A C2A B1A 114.97(12) . . ?
N1 C1 C2 119.95(13) . . ?
N1 C1 C6 121.29(13) . . ?
C6 C1 C2 118.75(13) . . ?
N1A C1A C2A 119.99(13) . . ?
N1A C1A C6A 121.46(13) . . ?
C6A C1A C2A 118.52(13) . . ?
C4A C3A C2A 122.66(14) . . ?
C5A C6A C1A 121.18(14) . . ?
C4 C3 C2 122.60(14) . . ?
C5 C6 C1 121.27(14) . . ?
O1 C9 C10 102.70(11) . . ?
O1 C9 C12 109.82(13) . . ?
O1 C9 C11 105.38(12) . . ?
C12 C9 C10 115.91(13) . . ?
C12 C9 C11 109.80(14) . . ?
C11 C9 C10 112.47(14) . . ?
C5A C4A C3A 118.18(14) . . ?
O1A C9A C10A 102.47(11) . . ?
O1A C9A C11A 108.25(13) . . ?
O1A C9A C12A 106.53(12) . . ?
C11A C9A C10A 114.66(13) . . ?
C11A C9A C12A 110.47(14) . . ?
C12A C9A C10A 113.68(14) . . ?
O2A C10A C9A 102.14(11) . . ?
O2A C10A C14A 108.23(13) . . ?
O2A C10A C13A 106.90(13) . . ?
C14A C10A C9A 115.09(15) . . ?
C14A C10A C13A 110.40(15) . . ?
C13A C10A C9A 113.31(14) . . ?
O2 C10 C9 102.95(11) . . ?
O2 C10 C14 106.01(13) . . ?
O2 C10 C13 109.52(14) . . ?
C14 C10 C9 111.38(14) . . ?
C13 C10 C9 115.77(15) . . ?
C13 C10 C14 110.51(16) . . ?
C6A C5A C4A 121.01(15) . . ?
C5 C4 C3 118.71(15) . . ?
C4 C5 C6 120.48(14) . . ?
O1A B1A O2A 112.65(13) . . ?
O1A B1A C2A 127.10(13) . . ?
O2A B1A C2A 120.16(12) . . ?
O1 B1 O2 112.72(12) . . ?
O1 B1 C2 126.50(13) . . ?
O2 B1 C2 120.65(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_eg032
_database_code_depnum_ccdc_archive 'CCDC 1995217'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 B F2 N O3'
_chemical_formula_sum            'C17 H24 B F2 N O3'
_chemical_formula_weight         339.18
_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/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                   9.0809(5)
_cell_length_b                   11.7860(6)
_cell_length_c                   15.8425(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.2640(10)
_cell_angle_gamma                90
_cell_volume                     1688.43(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4247
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.151
_cell_measurement_theta_min      2.252
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0588 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.9198. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22877
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.545
_diffrn_reflns_theta_min         2.157
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3910
_reflns_number_total             5142
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         -0.210
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         5142
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      1.006
_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)+(0.0486P)²+0.4231P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1072
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.81502(8) 0.59102(6) 0.71418(5) 0.02163(17) Uani 1 1 d . . . . .
F2 F 0.61957(8) 0.63951(6) 0.77570(4) 0.02175(17) Uani 1 1 d . . . . .
O2 O 0.71275(9) 0.71827(7) 0.55862(5) 0.01685(18) Uani 1 1 d . . . . .
O3 O 0.68628(9) 0.83334(7) 0.67630(5) 0.01827(18) Uani 1 1 d . . . . .
O1 O 0.47180(9) 0.73486(7) 0.62072(6) 0.01966(19) Uani 1 1 d . . . . .
N1 N 0.59217(11) 0.50825(8) 0.66888(6) 0.01469(19) Uani 1 1 d . . . . .
C3 C 0.38536(13) 0.64315(10) 0.62151(7) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.43218(12) 0.53283(10) 0.64421(7) 0.0152(2) Uani 1 1 d . . . . .
C1 C 0.66951(12) 0.61917(10) 0.69788(7) 0.0159(2) Uani 1 1 d . . . . .
C4 C 0.23334(13) 0.65940(11) 0.59849(8) 0.0188(2) Uani 1 1 d . . . . .
C12 C 0.75602(13) 0.83201(10) 0.53740(8) 0.0174(2) Uani 1 1 d . . . . .
C7 C 0.33234(14) 0.44264(11) 0.63966(8) 0.0195(2) Uani 1 1 d . . . . .
C11 C 0.66482(14) 0.45933(10) 0.59153(8) 0.0177(2) Uani 1 1 d . . . . .
C8 C 0.61654(14) 0.41617(11) 0.73945(8) 0.0182(2) Uani 1 1 d . . . . .
C13 C 0.79118(13) 0.88711(10) 0.62677(8) 0.0181(2) Uani 1 1 d . . . . .
C5 C 0.13397(14) 0.57020(11) 0.59529(8) 0.0213(3) Uani 1 1 d . . . . .
C6 C 0.18373(14) 0.46095(11) 0.61481(8) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.67603(15) 0.31317(11) 0.69604(8) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.62520(16) 0.88806(12) 0.48586(9) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.76435(15) 0.36404(11) 0.62764(8) 0.0218(3) Uani 1 1 d . . . . .
C15 C 0.88668(16) 0.82663(12) 0.48388(9) 0.0239(3) Uani 1 1 d . . . . .
C17 C 0.94683(15) 0.85887(13) 0.66638(9) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.76655(17) 1.01525(11) 0.62976(10) 0.0261(3) Uani 1 1 d . . . . .
B1 B 0.63734(14) 0.72891(11) 0.63508(8) 0.0161(2) Uani 1 1 d . . . . .
H8A H 0.6915(16) 0.4480(12) 0.7813(9) 0.016(3) Uiso 1 1 d . . . . .
H11A H 0.5822(15) 0.4302(12) 0.5532(9) 0.014(3) Uiso 1 1 d . . . . .
H4 H 0.2016(17) 0.7361(13) 0.5844(10) 0.023(4) Uiso 1 1 d . . . . .
H5 H 0.0295(18) 0.5845(14) 0.5797(10) 0.027(4) Uiso 1 1 d . . . . .
H14A H 0.5934(17) 0.8394(14) 0.4360(10) 0.026(4) Uiso 1 1 d . . . . .
H8B H 0.5244(16) 0.4037(12) 0.7646(9) 0.018(4) Uiso 1 1 d . . . . .
H14B H 0.5408(17) 0.8966(13) 0.5202(10) 0.023(4) Uiso 1 1 d . . . . .
H11B H 0.7108(16) 0.5211(13) 0.5638(10) 0.022(4) Uiso 1 1 d . . . . .
H17A H 0.9668(17) 0.7785(14) 0.6650(10) 0.026(4) Uiso 1 1 d . . . . .
H17B H 0.9577(19) 0.8832(14) 0.7271(12) 0.036(5) Uiso 1 1 d . . . . .
H16A H 0.8306(18) 1.0566(14) 0.5928(11) 0.031(4) Uiso 1 1 d . . . . .
H17C H 1.0245(19) 0.9000(14) 0.6367(11) 0.033(4) Uiso 1 1 d . . . . .
H16B H 0.6671(19) 1.0357(14) 0.6133(10) 0.027(4) Uiso 1 1 d . . . . .
H9A H 0.5944(18) 0.2657(14) 0.6705(10) 0.028(4) Uiso 1 1 d . . . . .
H15A H 0.9648(19) 0.7776(14) 0.5086(11) 0.031(4) Uiso 1 1 d . . . . .
H6 H 0.1170(18) 0.3993(14) 0.6128(11) 0.030(4) Uiso 1 1 d . . . . .
H10A H 0.7812(17) 0.3088(14) 0.5838(11) 0.028(4) Uiso 1 1 d . . . . .
H7 H 0.3666(17) 0.3663(14) 0.6542(10) 0.027(4) Uiso 1 1 d . . . . .
H9B H 0.7396(18) 0.2680(14) 0.7368(11) 0.031(4) Uiso 1 1 d . . . . .
H15B H 0.9303(19) 0.9040(15) 0.4785(11) 0.035(5) Uiso 1 1 d . . . . .
H10B H 0.8591(18) 0.3959(13) 0.6534(10) 0.026(4) Uiso 1 1 d . . . . .
H14C H 0.6542(18) 0.9653(15) 0.4657(11) 0.034(5) Uiso 1 1 d . . . . .
H15C H 0.8531(19) 0.7987(15) 0.4254(12) 0.038(5) Uiso 1 1 d . . . . .
H16C H 0.7940(19) 1.0426(15) 0.6883(12) 0.038(5) Uiso 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 C1 1.3639(13) . ?
F2 C1 1.3732(13) . ?
O2 C12 1.4451(14) . ?
O2 B1 1.4506(15) . ?
O3 C13 1.4360(14) . ?
O3 B1 1.4442(15) . ?
O1 C3 1.3366(14) . ?
O1 B1 1.5013(15) . ?
N1 C2 1.4978(14) . ?
N1 C1 1.5343(15) . ?
N1 C11 1.5549(15) . ?
N1 C8 1.5592(15) . ?
C3 C2 1.4045(16) . ?
C3 C4 1.4082(16) . ?
C2 C7 1.3947(17) . ?
C1 B1 1.6415(18) . ?
C4 C5 1.3833(18) . ?
C12 C13 1.5637(17) . ?
C12 C14 1.5286(17) . ?
C12 C15 1.5216(18) . ?
C7 C6 1.3875(18) . ?
C11 C10 1.5201(17) . ?
C8 C9 1.5189(18) . ?
C13 C17 1.5296(18) . ?
C13 C16 1.5280(18) . ?
C5 C6 1.3900(19) . ?
C9 C10 1.5286(18) . ?

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 O2 B1 105.87(9) . . ?
C13 O3 B1 108.72(9) . . ?
C3 O1 B1 122.79(9) . . ?
C2 N1 C1 108.64(9) . . ?
C2 N1 C11 109.73(9) . . ?
C2 N1 C8 113.09(9) . . ?
C1 N1 C11 109.65(9) . . ?
C1 N1 C8 110.33(9) . . ?
C11 N1 C8 105.33(9) . . ?
O1 C3 C2 125.93(10) . . ?
O1 C3 C4 116.76(10) . . ?
C2 C3 C4 117.31(11) . . ?
C3 C2 N1 120.63(10) . . ?
C7 C2 N1 118.46(10) . . ?
C7 C2 C3 120.81(11) . . ?
F1 C1 F2 105.46(9) . . ?
F1 C1 N1 104.97(9) . . ?
F1 C1 B1 114.95(9) . . ?
F2 C1 N1 103.75(9) . . ?
F2 C1 B1 110.58(9) . . ?
N1 C1 B1 116.02(9) . . ?
C5 C4 C3 121.79(12) . . ?
O2 C12 C13 102.24(9) . . ?
O2 C12 C14 108.09(10) . . ?
O2 C12 C15 109.49(10) . . ?
C14 C12 C13 112.85(10) . . ?
C15 C12 C13 114.64(11) . . ?
C15 C12 C14 109.13(11) . . ?
C6 C7 C2 120.46(12) . . ?
C10 C11 N1 104.96(9) . . ?
C9 C8 N1 105.35(9) . . ?
O3 C13 C12 102.76(9) . . ?
O3 C13 C17 108.30(10) . . ?
O3 C13 C16 108.23(10) . . ?
C17 C13 C12 112.66(10) . . ?
C16 C13 C12 114.85(11) . . ?
C16 C13 C17 109.55(11) . . ?
C4 C5 C6 119.88(12) . . ?
C7 C6 C5 119.67(12) . . ?
C8 C9 C10 103.83(10) . . ?
C11 C10 C9 102.94(10) . . ?
O2 B1 O1 114.86(10) . . ?
O2 B1 C1 111.51(10) . . ?
O3 B1 O2 107.58(10) . . ?
O3 B1 O1 106.92(9) . . ?
O3 B1 C1 111.54(10) . . ?
O1 B1 C1 104.40(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_eg007
_database_code_depnum_ccdc_archive 'CCDC 1995216'
loop_
_audit_author_name
_audit_author_address
'Alexander Korlyukov'
;INEOS RAS
Russia
;
_audit_update_record             
;
2020-04-07 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;
_audit_creation_date             2019-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H22 B F2 N O2'
_chemical_formula_sum            'C15 H22 B F2 N O2'
_chemical_formula_weight         297.14
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.6561(16)
_cell_length_b                   15.0608(13)
_cell_length_c                   19.6214(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3149.0(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1755
_cell_measurement_temperature    120
_cell_measurement_theta_max      72.101
_cell_measurement_theta_min      4.511
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.788
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1242 before and 0.0524 after correction. The Ratio of minimum to maximum transmission is 0.8336. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            35164
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.253
_diffrn_reflns_theta_min         4.507
_diffrn_ambient_temperature      120
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2821
_reflns_number_total             3095
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.329
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.038
_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)+(0.0496P)²+0.8844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0877
_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:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_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 0.31918(6) 0.76094(4) 0.70566(3) 0.02408(16) Uani 1 1 d . . . . .
F2 F 0.46786(6) 0.77783(4) 0.63196(3) 0.02774(17) Uani 1 1 d . . . . .
O1 O 0.20693(6) 0.64157(5) 0.60981(3) 0.01880(17) Uani 1 1 d . . . . .
O2 O 0.40482(7) 0.60677(5) 0.56499(4) 0.02188(18) Uani 1 1 d . . . . .
N1 N 0.49773(8) 0.67643(6) 0.71952(4) 0.0195(2) Uani 1 1 d . . . . .
C1 C 0.43523(9) 0.59192(7) 0.74121(5) 0.0186(2) Uani 1 1 d . . . . .
C2 C 0.35267(10) 0.55999(7) 0.69253(5) 0.0187(2) Uani 1 1 d . . . . .
C3 C 0.28884(10) 0.48194(7) 0.70924(5) 0.0213(2) Uani 1 1 d . . . . .
H3 H 0.2312 0.4569 0.6777 0.026 Uiso 1 1 calc R . . . .
C4 C 0.30917(11) 0.44069(7) 0.77179(6) 0.0243(2) Uani 1 1 d . . . . .
H4 H 0.2638 0.3884 0.7830 0.029 Uiso 1 1 calc R . . . .
C5 C 0.39531(11) 0.47527(7) 0.81813(5) 0.0255(2) Uani 1 1 d . . . . .
H5 H 0.4090 0.4457 0.8603 0.031 Uiso 1 1 calc R . . . .
C6 C 0.46129(10) 0.55238(7) 0.80344(5) 0.0226(2) Uani 1 1 d . . . . .
H6 H 0.5209 0.5767 0.8343 0.027 Uiso 1 1 calc R . . . .
C7 C 0.52358(11) 0.73857(7) 0.77775(6) 0.0248(2) Uani 1 1 d . . . . .
H7A H 0.4471 0.7461 0.8049 0.037 Uiso 1 1 calc GR . . . .
H7B H 0.5503 0.7963 0.7598 0.037 Uiso 1 1 calc GR . . . .
H7C H 0.5902 0.7138 0.8065 0.037 Uiso 1 1 calc GR . . . .
C8 C 0.61790(10) 0.65401(8) 0.68271(6) 0.0263(2) Uani 1 1 d . . . . .
H8A H 0.6712 0.6176 0.7123 0.039 Uiso 1 1 calc GR . . . .
H8B H 0.6622 0.7089 0.6709 0.039 Uiso 1 1 calc GR . . . .
H8C H 0.5984 0.6209 0.6410 0.039 Uiso 1 1 calc GR . . . .
C9 C 0.40351(10) 0.71449(7) 0.66691(5) 0.0195(2) Uani 1 1 d . . . . .
C10 C 0.20117(10) 0.65324(7) 0.53696(5) 0.0195(2) Uani 1 1 d . . . . .
C11 C 0.31328(10) 0.59477(7) 0.51196(5) 0.0210(2) Uani 1 1 d . . . . .
C12 C 0.07194(10) 0.62283(8) 0.51384(6) 0.0251(2) Uani 1 1 d . . . . .
H12A H 0.0582 0.5613 0.5283 0.038 Uiso 1 1 calc GR . . . .
H12B H 0.0665 0.6265 0.4641 0.038 Uiso 1 1 calc GR . . . .
H12C H 0.0077 0.6611 0.5343 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.21866(12) 0.75173(8) 0.52083(6) 0.0278(2) Uani 1 1 d . . . . .
H13A H 0.1578 0.7867 0.5469 0.042 Uiso 1 1 calc GR . . . .
H13B H 0.2055 0.7617 0.4720 0.042 Uiso 1 1 calc GR . . . .
H13C H 0.3039 0.7699 0.5332 0.042 Uiso 1 1 calc GR . . . .
C14 C 0.28024(11) 0.49616(8) 0.50773(6) 0.0277(3) Uani 1 1 d . . . . .
H14A H 0.3568 0.4616 0.4999 0.042 Uiso 1 1 calc GR . . . .
H14B H 0.2216 0.4864 0.4700 0.042 Uiso 1 1 calc GR . . . .
H14C H 0.2412 0.4773 0.5506 0.042 Uiso 1 1 calc GR . . . .
C15 C 0.37085(12) 0.62442(9) 0.44440(6) 0.0300(3) Uani 1 1 d . . . . .
H15A H 0.4048 0.6846 0.4493 0.045 Uiso 1 1 calc GR . . . .
H15B H 0.3062 0.6241 0.4089 0.045 Uiso 1 1 calc GR . . . .
H15C H 0.4385 0.5836 0.4317 0.045 Uiso 1 1 calc GR . . . .
B1 B 0.33753(11) 0.62696(8) 0.62763(6) 0.0180(2) 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 C9 1.3693(12) . ?
F2 C9 1.3602(12) . ?
O1 C10 1.4417(12) . ?
O1 B1 1.4517(13) . ?
O2 C11 1.4376(12) . ?
O2 B1 1.4551(13) . ?
N1 C1 1.4982(13) . ?
N1 C7 1.5024(14) . ?
N1 C8 1.5084(13) . ?
N1 C9 1.5500(13) . ?
C1 C2 1.3847(15) . ?
C1 C6 1.3867(14) . ?
C2 C3 1.3970(15) . ?
C2 B1 1.6325(15) . ?
C3 C4 1.3925(15) . ?
C4 C5 1.3930(16) . ?
C5 C6 1.3878(16) . ?
C9 B1 1.6812(15) . ?
C10 C11 1.5631(14) . ?
C10 C12 1.5204(14) . ?
C10 C13 1.5281(15) . ?
C11 C14 1.5285(15) . ?
C11 C15 1.5275(14) . ?

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 107.34(7) . . ?
C11 O2 B1 107.65(8) . . ?
C1 N1 C7 113.25(8) . . ?
C1 N1 C8 108.86(8) . . ?
C1 N1 C9 102.44(7) . . ?
C7 N1 C8 110.36(8) . . ?
C7 N1 C9 113.26(8) . . ?
C8 N1 C9 108.29(8) . . ?
C2 C1 N1 112.43(9) . . ?
C2 C1 C6 125.84(10) . . ?
C6 C1 N1 121.73(9) . . ?
C1 C2 C3 116.08(9) . . ?
C1 C2 B1 112.72(9) . . ?
C3 C2 B1 130.90(9) . . ?
C4 C3 C2 120.43(10) . . ?
C3 C4 C5 120.73(10) . . ?
C6 C5 C4 120.74(10) . . ?
C1 C6 C5 116.15(10) . . ?
F1 C9 N1 104.14(8) . . ?
F1 C9 B1 112.37(8) . . ?
F2 C9 F1 104.63(8) . . ?
F2 C9 N1 105.58(8) . . ?
F2 C9 B1 121.98(8) . . ?
N1 C9 B1 106.63(8) . . ?
O1 C10 C11 102.11(8) . . ?
O1 C10 C12 107.32(8) . . ?
O1 C10 C13 108.57(8) . . ?
C12 C10 C11 115.40(9) . . ?
C12 C10 C13 109.94(9) . . ?
C13 C10 C11 112.87(9) . . ?
O2 C11 C10 102.75(8) . . ?
O2 C11 C14 108.53(8) . . ?
O2 C11 C15 108.60(9) . . ?
C14 C11 C10 112.85(9) . . ?
C15 C11 C10 114.49(9) . . ?
C15 C11 C14 109.23(9) . . ?
O1 B1 O2 107.50(8) . . ?
O1 B1 C2 112.10(8) . . ?
O1 B1 C9 113.11(8) . . ?
O2 B1 C2 118.75(9) . . ?
O2 B1 C9 110.18(8) . . ?
C2 B1 C9 94.91(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
