# 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_testm1_tw
_database_code_depnum_ccdc_archive 'CCDC 2061359'
loop_
_audit_author_name
_audit_author_address
'Hazel Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-06-22 downloaded from the CCDC.
;
_audit_creation_date             2021-02-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H8 Br F2 N O'
_chemical_formula_sum            'C11 H8 Br F2 N O'
_chemical_formula_weight         288.09
_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'
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'

_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                   7.3373(5)
_cell_length_b                   14.2535(9)
_cell_length_c                   9.9567(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.050(4)
_cell_angle_gamma                90
_cell_volume                     1041.29(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7253
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.693
_shelx_estimated_absorpt_T_min   0.288
_exptl_absorpt_coefficient_mu    3.951
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0682 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.6915.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2506
_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         28.053
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2388
_reflns_number_total             2506
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.884
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2506
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.184
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0257P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0640
_refine_ls_wR_factor_ref         0.0647
_refine_special_details          'Refined as a two component twin.'
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H8(0.015) H10(0.02) H11A(0.032) H11B(0.032) H11C(0.032) H4(0.022)
 H2(0.026) H3(0.027)
 Fixed X: H8(0.165539) H10(0.261852) H11A(0.239843) H11B(0.041484)
 H11C(0.079925) H4(0.220704) H2(0.365588) H3(0.305563)
 Fixed Y: H8(0.64567) H10(0.764662) H11A(0.448021) H11B(0.421484)
 H11C(0.524344) H4(0.312355) H2(0.324522) H3(0.238095)
 Fixed Z: H8(0.184564) H10(0.090833) H11A(0.353081) H11B(0.297967)
 H11C(0.355862) H4(0.146965) H2(-0.245749) H3(-0.051711)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.37412(6) 0.51475(2) -0.32876(5) 0.01927(8) Uani 1 1 d . . . . .
F1 F 0.3560(3) 0.82961(12) -0.06868(18) 0.0247(4) Uani 1 1 d . . . . .
F2 F 0.0682(3) 0.82180(15) -0.0184(2) 0.0322(5) Uani 1 1 d . . . . .
O1 O 0.1856(4) 0.68917(17) -0.2032(2) 0.0238(6) Uani 1 1 d . . . . .
N1 N 0.1850(3) 0.50352(16) 0.1707(3) 0.0144(5) Uani 1 1 d . . . . .
C8 C 0.1885(4) 0.5927(2) 0.1291(3) 0.0124(6) Uani 1 1 d . . . . .
H8 H 0.165539 0.645670 0.184564 0.015 Uiso 1 1 calc R U . . .
C9 C 0.2153(4) 0.6828(2) -0.0830(3) 0.0148(6) Uani 1 1 d . . . . .
C10 C 0.2296(4) 0.7753(2) -0.0056(3) 0.0170(6) Uani 1 1 d . . . . .
H10 H 0.261852 0.764662 0.090833 0.020 Uiso 1 1 calc R U . . .
C11 C 0.1322(6) 0.4717(2) 0.3057(3) 0.0215(8) Uani 1 1 d . . . . .
H11A H 0.239843 0.448021 0.353081 0.032 Uiso 1 1 calc R U . . .
H11B H 0.041484 0.421484 0.297967 0.032 Uiso 1 1 calc R U . . .
H11C H 0.079925 0.524344 0.355862 0.032 Uiso 1 1 calc R U . . .
C1 C 0.3131(4) 0.4525(2) -0.1663(3) 0.0158(5) Uani 1 1 d . . . . .
C6 C 0.2595(4) 0.5007(2) -0.0511(3) 0.0126(6) Uani 1 1 d . . . . .
C4 C 0.2443(4) 0.3474(2) 0.0677(3) 0.0186(6) Uani 1 1 d . . . . .
H4 H 0.220704 0.312355 0.146965 0.022 Uiso 1 1 calc R U . . .
C2 C 0.3298(4) 0.3561(2) -0.1660(4) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.365588 0.324522 -0.245749 0.026 Uiso 1 1 calc R U . . .
C5 C 0.2295(4) 0.4449(2) 0.0655(3) 0.0124(5) Uani 1 1 d . . . . .
C7 C 0.2307(4) 0.5969(2) -0.0075(3) 0.0129(5) Uani 1 1 d . . . . .
C3 C 0.2945(5) 0.3045(2) -0.0495(4) 0.0225(7) Uani 1 1 d . . . . .
H3 H 0.305563 0.238095 -0.051711 0.027 Uiso 1 1 calc R U . . .


_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
Br1 C1 1.899(3) . ?
F1 C10 1.362(3) . ?
F2 C10 1.363(4) . ?
O1 C9 1.220(4) . ?
N1 C8 1.338(4) . ?
N1 C11 1.471(4) . ?
N1 C5 1.378(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.396(4) . ?
C9 C10 1.531(4) . ?
C9 C7 1.441(4) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C1 C6 1.394(4) . ?
C1 C2 1.379(4) . ?
C6 C5 1.424(4) . ?
C6 C7 1.455(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.395(4) . ?
C4 C3 1.368(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.399(5) . ?
C3 H3 0.9500 . ?

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
C8 N1 C11 125.5(3) . . ?
C8 N1 C5 109.7(3) . . ?
C5 N1 C11 124.7(2) . . ?
N1 C8 H8 124.9 . . ?
N1 C8 C7 110.3(3) . . ?
C7 C8 H8 124.9 . . ?
O1 C9 C10 116.2(3) . . ?
O1 C9 C7 126.1(3) . . ?
C7 C9 C10 117.6(3) . . ?
F1 C10 F2 105.8(2) . . ?
F1 C10 C9 107.7(2) . . ?
F1 C10 H10 111.6 . . ?
F2 C10 C9 108.2(3) . . ?
F2 C10 H10 111.6 . . ?
C9 C10 H10 111.6 . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C1 Br1 122.5(2) . . ?
C2 C1 Br1 116.5(3) . . ?
C2 C1 C6 120.9(3) . . ?
C1 C6 C5 116.1(3) . . ?
C1 C6 C7 138.7(3) . . ?
C5 C6 C7 105.1(2) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C3 C4 C5 117.0(3) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
N1 C5 C6 108.6(2) . . ?
N1 C5 C4 127.6(3) . . ?
C4 C5 C6 123.8(3) . . ?
C8 C7 C9 121.8(3) . . ?
C8 C7 C6 106.4(2) . . ?
C9 C7 C6 131.1(3) . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?

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
Br1 C1 C6 C5 -176.1(2) . . . . ?
Br1 C1 C6 C7 -0.1(5) . . . . ?
Br1 C1 C2 C3 177.6(2) . . . . ?
O1 C9 C10 F1 -53.5(4) . . . . ?
O1 C9 C10 F2 60.4(4) . . . . ?
O1 C9 C7 C8 -152.4(3) . . . . ?
O1 C9 C7 C6 16.6(5) . . . . ?
N1 C8 C7 C9 170.0(3) . . . . ?
N1 C8 C7 C6 -1.4(3) . . . . ?
C8 N1 C5 C6 -1.3(3) . . . . ?
C8 N1 C5 C4 178.7(3) . . . . ?
C10 C9 C7 C8 24.9(4) . . . . ?
C10 C9 C7 C6 -166.0(3) . . . . ?
C11 N1 C8 C7 -175.2(3) . . . . ?
C11 N1 C5 C6 175.7(3) . . . . ?
C11 N1 C5 C4 -4.3(5) . . . . ?
C1 C6 C5 N1 177.6(2) . . . . ?
C1 C6 C5 C4 -2.4(5) . . . . ?
C1 C6 C7 C8 -175.6(4) . . . . ?
C1 C6 C7 C9 14.1(6) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C6 C1 C2 C3 -0.5(5) . . . . ?
C2 C1 C6 C5 1.9(4) . . . . ?
C2 C1 C6 C7 177.9(3) . . . . ?
C5 N1 C8 C7 1.7(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C9 -169.7(3) . . . . ?
C5 C4 C3 C2 0.2(5) . . . . ?
C7 C9 C10 F1 128.9(3) . . . . ?
C7 C9 C10 F2 -117.2(3) . . . . ?
C7 C6 C5 N1 0.3(3) . . . . ?
C7 C6 C5 C4 -179.7(3) . . . . ?
C3 C4 C5 N1 -178.6(3) . . . . ?
C3 C4 C5 C6 1.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.271(18)
2 0.241(8)
3 0.488(16)

