# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_gil9967
_database_code_depnum_ccdc_archive 'CCDC 2055892'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.11-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br F2 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         380.19

_chemical_melting_point          ?

_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                   4.7731(8)
_cell_length_b                   11.3543(17)
_cell_length_c                   14.650(2)
_cell_angle_alpha                67.712(5)
_cell_angle_beta                 85.665(5)
_cell_angle_gamma                88.114(6)
_cell_volume                     732.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6241
_cell_measurement_theta_min      2.8698
_cell_measurement_theta_max      26.8468
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.149
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.043
_exptl_crystal_density_diffrn    1.724
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380

_exptl_absorpt_coefficient_mu    2.837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption
correction. Reference: Krause, L., Herbst-Irmer, R., Sheldrick G.M.
& Stalke D., J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  0.89

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   MoK\a
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            14235
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17

_refine_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_number_total             2620
_reflns_number_gt                2325
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0779
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0384P)²+0.5703P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.485
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Br Br -0.2901 2.4595 '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'

_computing_data_collection       'Bruker APEX3 v2019.11-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 -0.27688(6) 0.16413(3) 0.96951(2) 0.02107(11) Uani d . . . 1 . .
N N1 0.4469(5) 0.3033(2) 0.34605(16) 0.0140(5) Uani d . . . 1 . .
O O1 0.5242(4) 0.5187(2) 0.31450(14) 0.0178(4) Uani d . . . 1 . .
O O2 0.4853(4) 0.1066(2) 0.32879(15) 0.0194(5) Uani d . . . 1 . .
C C1 0.2360(6) 0.2741(3) 0.4271(2) 0.0146(6) Uani d . . . 1 . .
C C2 0.2098(6) 0.1492(3) 0.4968(2) 0.0166(6) Uani d . . . 1 . .
H H2 0.329733 0.083735 0.490592 0.02 Uiso calc U . R 1 . .
C C3 0.0056(6) 0.1218(3) 0.5754(2) 0.0159(6) Uani d . . . 1 . .
H H3 -0.01569 0.036648 0.621565 0.019 Uiso calc U . R 1 . .
C C4 -0.1657(6) 0.2158(3) 0.5872(2) 0.0148(6) Uani d . . . 1 . .
C C5 -0.1370(6) 0.3396(3) 0.5173(2) 0.0153(6) Uani d . . . 1 . .
H H5 -0.25483 0.405115 0.524375 0.018 Uiso calc U . R 1 . .
C C6 0.0619(6) 0.3691(3) 0.4370(2) 0.0155(6) Uani d . . . 1 . .
H H6 0.077633 0.453745 0.389496 0.019 Uiso calc U . R 1 . .
C C7 -0.3774(6) 0.1878(3) 0.6756(2) 0.0155(6) Uani d . . . 1 . .
H H7A -0.522126 0.255745 0.659896 0.019 Uiso calc U . R 1 . .
H H7B -0.472483 0.106345 0.688149 0.019 Uiso calc U . R 1 . .
C C8 -0.2421(6) 0.1791(3) 0.7685(2) 0.0161(6) Uani d . . . 1 . .
F F1 -0.0729(3) 0.07242(16) 0.80056(12) 0.0211(4) Uani d . . . 1 . .
F F2 -0.0606(3) 0.27967(16) 0.74733(12) 0.0183(4) Uani d . . . 1 . .
C C9 -0.4552(6) 0.1774(3) 0.8504(2) 0.0186(6) Uani d . . . 1 . .
H H9A -0.583073 0.10431 0.866293 0.022 Uiso calc U . R 1 . .
H H9B -0.569404 0.256298 0.827539 0.022 Uiso calc U . R 1 . .
C C10 0.5768(6) 0.4243(3) 0.2982(2) 0.0150(6) Uani d . . . 1 . .
C C11 0.7952(6) 0.4079(3) 0.2248(2) 0.0147(6) Uani d . . . 1 . .
C C12 0.9854(6) 0.4954(3) 0.1610(2) 0.0174(6) Uani d . . . 1 . .
H H12 0.989826 0.580553 0.157526 0.021 Uiso calc U . R 1 . .
C C13 1.1705(6) 0.4522(3) 0.1021(2) 0.0200(7) Uani d . . . 1 . .
H H13 1.304975 0.509291 0.057416 0.024 Uiso calc U . R 1 . .
C C14 1.1628(6) 0.3277(3) 0.1072(2) 0.0196(6) Uani d . . . 1 . .
H H14 1.291713 0.301354 0.065901 0.024 Uiso calc U . R 1 . .
C C15 0.9686(6) 0.2405(3) 0.1719(2) 0.0176(6) Uani d . . . 1 . .
H H15 0.96223 0.155243 0.175623 0.021 Uiso calc U . R 1 . .
C C16 0.7867(6) 0.2838(3) 0.2302(2) 0.0155(6) Uani d . . . 1 . .
C C17 0.5605(6) 0.2153(3) 0.3061(2) 0.0151(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C9 . 1.952(3) ?
N1 C17 . 1.413(4) ?
N1 C10 . 1.422(4) ?
N1 C1 . 1.441(3) ?
O1 C10 . 1.199(4) ?
O2 C17 . 1.208(4) ?
C1 C6 . 1.384(4) ?
C1 C2 . 1.402(4) ?
C2 C3 . 1.397(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.379(4) ?
C3 H3 . 0.95 ?
C4 C5 . 1.394(4) ?
C4 C7 . 1.520(4) ?
C5 C6 . 1.397(4) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 C8 . 1.518(4) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 F1 . 1.379(3) ?
C8 F2 . 1.381(3) ?
C8 C9 . 1.508(4) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 C11 . 1.498(4) ?
C11 C16 . 1.382(4) ?
C11 C12 . 1.383(4) ?
C12 C13 . 1.394(4) ?
C12 H12 . 0.95 ?
C13 C14 . 1.389(5) ?
C13 H13 . 0.95 ?
C14 C15 . 1.398(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.380(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.492(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C17 N1 C10 . . 110.9(2) ?
C17 N1 C1 . . 124.9(2) ?
C10 N1 C1 . . 124.1(2) ?
C6 C1 C2 . . 120.0(3) ?
C6 C1 N1 . . 120.3(3) ?
C2 C1 N1 . . 119.7(3) ?
C3 C2 C1 . . 119.3(3) ?
C3 C2 H2 . . 120.3 ?
C1 C2 H2 . . 120.3 ?
C4 C3 C2 . . 121.3(3) ?
C4 C3 H3 . . 119.3 ?
C2 C3 H3 . . 119.3 ?
C3 C4 C5 . . 118.6(3) ?
C3 C4 C7 . . 121.5(3) ?
C5 C4 C7 . . 119.9(3) ?
C4 C5 C6 . . 121.2(3) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C1 C6 C5 . . 119.5(3) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
C8 C7 C4 . . 112.5(2) ?
C8 C7 H7A . . 109.1 ?
C4 C7 H7A . . 109.1 ?
C8 C7 H7B . . 109.1 ?
C4 C7 H7B . . 109.1 ?
H7A C7 H7B . . 107.8 ?
F1 C8 F2 . . 104.5(2) ?
F1 C8 C9 . . 110.0(2) ?
F2 C8 C9 . . 109.3(2) ?
F1 C8 C7 . . 110.0(2) ?
F2 C8 C7 . . 110.1(2) ?
C9 C8 C7 . . 112.6(2) ?
C8 C9 Br1 . . 111.88(19) ?
C8 C9 H9A . . 109.2 ?
Br1 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
Br1 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
O1 C10 N1 . . 126.9(3) ?
O1 C10 C11 . . 127.5(3) ?
N1 C10 C11 . . 105.6(2) ?
C16 C11 C12 . . 122.1(3) ?
C16 C11 C10 . . 108.7(2) ?
C12 C11 C10 . . 129.2(3) ?
C11 C12 C13 . . 116.6(3) ?
C11 C12 H12 . . 121.7 ?
C13 C12 H12 . . 121.7 ?
C14 C13 C12 . . 121.5(3) ?
C14 C13 H13 . . 119.2 ?
C12 C13 H13 . . 119.2 ?
C13 C14 C15 . . 121.2(3) ?
C13 C14 H14 . . 119.4 ?
C15 C14 H14 . . 119.4 ?
C16 C15 C14 . . 117.0(3) ?
C16 C15 H15 . . 121.5 ?
C14 C15 H15 . . 121.5 ?
C15 C16 C11 . . 121.6(3) ?
C15 C16 C17 . . 129.9(3) ?
C11 C16 C17 . . 108.4(3) ?
O2 C17 N1 . . 126.3(3) ?
O2 C17 C16 . . 127.4(3) ?
N1 C17 C16 . . 106.3(2) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C17 N1 C1 C6 . . . . -154.9(3) ?
C10 N1 C1 C6 . . . . 27.7(4) ?
C17 N1 C1 C2 . . . . 25.9(4) ?
C10 N1 C1 C2 . . . . -151.4(3) ?
C6 C1 C2 C3 . . . . 0.5(4) ?
N1 C1 C2 C3 . . . . 179.7(2) ?
C1 C2 C3 C4 . . . . -1.8(4) ?
C2 C3 C4 C5 . . . . 1.8(4) ?
C2 C3 C4 C7 . . . . -176.7(2) ?
C3 C4 C5 C6 . . . . -0.5(4) ?
C7 C4 C5 C6 . . . . 178.0(2) ?
C2 C1 C6 C5 . . . . 0.7(4) ?
N1 C1 C6 C5 . . . . -178.5(2) ?
C4 C5 C6 C1 . . . . -0.7(4) ?
C3 C4 C7 C8 . . . . 78.8(3) ?
C5 C4 C7 C8 . . . . -99.6(3) ?
C4 C7 C8 F1 . . . . -68.3(3) ?
C4 C7 C8 F2 . . . . 46.3(3) ?
C4 C7 C8 C9 . . . . 168.6(3) ?
F1 C8 C9 Br1 . . . . 56.3(3) ?
F2 C8 C9 Br1 . . . . -57.9(3) ?
C7 C8 C9 Br1 . . . . 179.31(19) ?
C17 N1 C10 O1 . . . . 179.0(3) ?
C1 N1 C10 O1 . . . . -3.3(4) ?
C17 N1 C10 C11 . . . . -1.9(3) ?
C1 N1 C10 C11 . . . . 175.7(2) ?
O1 C10 C11 C16 . . . . 179.7(3) ?
N1 C10 C11 C16 . . . . 0.7(3) ?
O1 C10 C11 C12 . . . . 0.9(5) ?
N1 C10 C11 C12 . . . . -178.1(3) ?
C16 C11 C12 C13 . . . . -0.2(4) ?
C10 C11 C12 C13 . . . . 178.5(3) ?
C11 C12 C13 C14 . . . . 0.2(4) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . -0.1(4) ?
C14 C15 C16 C11 . . . . 0.1(4) ?
C14 C15 C16 C17 . . . . -179.5(3) ?
C12 C11 C16 C15 . . . . 0.0(4) ?
C10 C11 C16 C15 . . . . -178.9(2) ?
C12 C11 C16 C17 . . . . 179.7(2) ?
C10 C11 C16 C17 . . . . 0.8(3) ?
C10 N1 C17 O2 . . . . -176.9(3) ?
C1 N1 C17 O2 . . . . 5.4(4) ?
C10 N1 C17 C16 . . . . 2.4(3) ?
C1 N1 C17 C16 . . . . -175.3(2) ?
C15 C16 C17 O2 . . . . -3.0(5) ?
C11 C16 C17 O2 . . . . 177.4(3) ?
C15 C16 C17 N1 . . . . 177.7(3) ?
C11 C16 C17 N1 . . . . -1.9(3) ?



#=============================================================================
#  end of cif data for "gil9967"  (compound 15)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

