# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1881797'
_audit_update_record             
;
2018-11-28 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H9 Br F N O3'
_chemical_formula_weight         398.18

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0015 0.0009 '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'
N N 0.0030 0.0019 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0056 0.0036 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0096 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br 0.1811 1.6452 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   7.3505(4)
_cell_length_b                   15.9493(9)
_cell_length_c                   13.0154(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.358(3)
_cell_angle_gamma                90
_cell_volume                     1519.20(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.741
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    1.472
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.56086
_diffrn_radiation_type           AgK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43490
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.015
_diffrn_reflns_theta_max         21.989
_diffrn_reflns_theta_full        19.665
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3787
_reflns_number_gt                2951
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+1.7226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0810
_refine_ls_wR_factor_gt          0.0739
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
C1 C 0.2368(3) 0.58619(14) 0.29719(18) 0.0171(5) Uani 1 1 d . . . . .
C2 C 0.1907(3) 0.51270(15) 0.34370(19) 0.0178(5) Uani 1 1 d . . . . .
C3 C 0.2447(3) 0.51935(15) 0.45344(19) 0.0179(5) Uani 1 1 d . . . . .
C4 C 0.2349(4) 0.46881(16) 0.5397(2) 0.0211(5) Uani 1 1 d . . . . .
H4 H 0.181852 0.414497 0.534309 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3066(4) 0.50126(16) 0.63486(19) 0.0215(5) Uani 1 1 d . . . . .
C6 C 0.3873(3) 0.57948(16) 0.64776(19) 0.0212(5) Uani 1 1 d . . . . .
H6 H 0.434194 0.598218 0.714298 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3984(4) 0.63041(15) 0.56109(19) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.3236(3) 0.59836(15) 0.46810(18) 0.0172(5) Uani 1 1 d . . . . .
C9 C 0.4140(4) 0.71319(15) 0.36873(19) 0.0186(5) Uani 1 1 d . . . . .
H9 H 0.422635 0.739123 0.303653 0.022 Uiso 1 1 calc R U . . .
C10 C 0.4940(4) 0.74960(15) 0.45578(19) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.4867(4) 0.71335(16) 0.56018(19) 0.0212(5) Uani 1 1 d . . . . .
C12 C 0.1969(3) 0.61375(15) 0.19000(18) 0.0174(5) Uani 1 1 d . . . . .
C13 C 0.1074(4) 0.68954(15) 0.16757(19) 0.0201(5) Uani 1 1 d . . . . .
H13 H 0.079888 0.725557 0.222155 0.024 Uiso 1 1 calc R U . . .
C14 C 0.0583(4) 0.71264(16) 0.0661(2) 0.0249(6) Uani 1 1 d . . . . .
H14 H -0.003790 0.763942 0.050287 0.030 Uiso 1 1 calc R U . . .
C15 C 0.1015(4) 0.65955(17) -0.0107(2) 0.0259(6) Uani 1 1 d . . . . .
C16 C 0.1904(4) 0.58508(16) 0.0078(2) 0.0261(6) Uani 1 1 d . . . . .
H16 H 0.218318 0.550028 -0.047584 0.031 Uiso 1 1 calc R U . . .
C17 C 0.2386(4) 0.56190(15) 0.1089(2) 0.0225(5) Uani 1 1 d . . . . .
H17 H 0.300498 0.510354 0.123425 0.027 Uiso 1 1 calc R U . . .
C18 C 0.5960(4) 0.83264(15) 0.44627(19) 0.0197(5) Uani 1 1 d . . . . .
H18A H 0.661997 0.855270 0.506134 0.024 Uiso 0.890(6) 1 calc R U P A 1
H18B H 0.609656 0.858746 0.381838 0.024 Uiso 0.110(6) 1 calc R U P A 2
C19 C 0.0992(4) 0.44069(15) 0.2931(2) 0.0230(5) Uani 1 1 d . . . . .
H19 H 0.064618 0.443374 0.221024 0.028 Uiso 1 1 calc R U . . .
N1 N 0.3208(3) 0.63919(12) 0.37435(15) 0.0172(4) Uani 1 1 d . . . . .
O1 O 0.5497(3) 0.74975(12) 0.63897(14) 0.0313(5) Uani 1 1 d . . . . .
O2A O 0.5960(4) 0.86860(14) 0.37007(18) 0.0380(8) Uani 0.890(6) 1 d . . P A 1
O2B O 0.657(3) 0.8618(13) 0.5271(14) 0.040(6) Uani 0.110(6) 1 d . . P A 2
O3 O 0.0657(3) 0.37774(12) 0.33928(16) 0.0356(5) Uani 1 1 d . . . . .
F1 F 0.0556(3) 0.68327(11) -0.11003(12) 0.0402(5) Uani 1 1 d . . . . .
Br1 Br 0.29356(4) 0.43101(2) 0.75255(2) 0.02941(9) 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
C1 C2 1.376(3) . ?
C1 N1 1.410(3) . ?
C1 C12 1.466(3) . ?
C2 C3 1.450(3) . ?
C2 C19 1.457(3) . ?
C3 C4 1.389(3) . ?
C3 C8 1.393(3) . ?
C4 C5 1.399(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 Br1 1.908(2) . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C7 C11 1.474(4) . ?
C8 N1 1.382(3) . ?
C9 C10 1.357(3) . ?
C9 N1 1.370(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.482(3) . ?
C10 C18 1.532(3) . ?
C11 O1 1.231(3) . ?
C12 C13 1.394(3) . ?
C12 C17 1.397(3) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9500 . ?
C15 F1 1.358(3) . ?
C15 C16 1.366(4) . ?
C16 C17 1.381(4) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 O2A 1.146(3) . ?
C18 O2B 1.20(2) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C19 O3 1.207(3) . ?
C19 H19 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
C2 C1 N1 107.9(2) . . ?
C2 C1 C12 129.7(2) . . ?
N1 C1 C12 122.2(2) . . ?
C1 C2 C3 108.4(2) . . ?
C1 C2 C19 126.5(2) . . ?
C3 C2 C19 125.1(2) . . ?
C4 C3 C8 117.8(2) . . ?
C4 C3 C2 136.4(2) . . ?
C8 C3 C2 105.8(2) . . ?
C3 C4 C5 117.2(2) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 124.2(2) . . ?
C6 C5 Br1 119.00(19) . . ?
C4 C5 Br1 116.78(19) . . ?
C5 C6 C7 118.8(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C8 C7 C6 116.3(2) . . ?
C8 C7 C11 117.7(2) . . ?
C6 C7 C11 125.9(2) . . ?
C7 C8 N1 124.9(2) . . ?
C7 C8 C3 125.6(2) . . ?
N1 C8 C3 109.5(2) . . ?
C10 C9 N1 120.3(2) . . ?
C10 C9 H9 119.9 . . ?
N1 C9 H9 119.9 . . ?
C9 C10 C11 123.3(2) . . ?
C9 C10 C18 118.6(2) . . ?
C11 C10 C18 118.1(2) . . ?
O1 C11 C7 123.3(2) . . ?
O1 C11 C10 122.5(2) . . ?
C7 C11 C10 114.3(2) . . ?
C13 C12 C17 119.2(2) . . ?
C13 C12 C1 120.5(2) . . ?
C17 C12 C1 120.2(2) . . ?
C14 C13 C12 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 118.3(2) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
F1 C15 C16 118.9(2) . . ?
F1 C15 C14 117.9(2) . . ?
C16 C15 C14 123.2(2) . . ?
C15 C16 C17 118.5(2) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C12 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
O2A C18 C10 122.8(2) . . ?
O2B C18 C10 114.2(10) . . ?
O2A C18 H18A 118.6 . . ?
C10 C18 H18A 118.6 . . ?
O2B C18 H18B 122.9 . . ?
C10 C18 H18B 122.9 . . ?
O3 C19 C2 122.5(2) . . ?
O3 C19 H19 118.7 . . ?
C2 C19 H19 118.7 . . ?
C9 N1 C8 119.1(2) . . ?
C9 N1 C1 131.8(2) . . ?
C8 N1 C1 108.41(19) . . ?

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
N1 C1 C2 C3 0.7(3) . . . . ?
C12 C1 C2 C3 -173.9(2) . . . . ?
N1 C1 C2 C19 179.3(2) . . . . ?
C12 C1 C2 C19 4.7(4) . . . . ?
C1 C2 C3 C4 179.3(3) . . . . ?
C19 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C8 -0.3(3) . . . . ?
C19 C2 C3 C8 -178.9(2) . . . . ?
C8 C3 C4 C5 -0.4(4) . . . . ?
C2 C3 C4 C5 -180.0(3) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C3 C4 C5 Br1 -179.68(18) . . . . ?
C4 C5 C6 C7 0.3(4) . . . . ?
Br1 C5 C6 C7 179.28(19) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C5 C6 C7 C11 -177.1(2) . . . . ?
C6 C7 C8 N1 179.8(2) . . . . ?
C11 C7 C8 N1 -1.8(4) . . . . ?
C6 C7 C8 C3 -2.3(4) . . . . ?
C11 C7 C8 C3 176.1(2) . . . . ?
C4 C3 C8 C7 1.9(4) . . . . ?
C2 C3 C8 C7 -178.3(2) . . . . ?
C4 C3 C8 N1 -179.9(2) . . . . ?
C2 C3 C8 N1 -0.2(3) . . . . ?
N1 C9 C10 C11 -0.1(4) . . . . ?
N1 C9 C10 C18 -179.6(2) . . . . ?
C8 C7 C11 O1 176.3(3) . . . . ?
C6 C7 C11 O1 -5.6(4) . . . . ?
C8 C7 C11 C10 -3.9(3) . . . . ?
C6 C7 C11 C10 174.3(2) . . . . ?
C9 C10 C11 O1 -175.2(3) . . . . ?
C18 C10 C11 O1 4.3(4) . . . . ?
C9 C10 C11 C7 5.0(4) . . . . ?
C18 C10 C11 C7 -175.5(2) . . . . ?
C2 C1 C12 C13 124.5(3) . . . . ?
N1 C1 C12 C13 -49.4(4) . . . . ?
C2 C1 C12 C17 -51.6(4) . . . . ?
N1 C1 C12 C17 134.5(3) . . . . ?
C17 C12 C13 C14 0.8(4) . . . . ?
C1 C12 C13 C14 -175.4(2) . . . . ?
C12 C13 C14 C15 -0.6(4) . . . . ?
C13 C14 C15 F1 -178.9(2) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
F1 C15 C16 C17 179.2(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C12 0.0(4) . . . . ?
C13 C12 C17 C16 -0.5(4) . . . . ?
C1 C12 C17 C16 175.7(2) . . . . ?
C9 C10 C18 O2A 6.1(4) . . . . ?
C11 C10 C18 O2A -173.4(3) . . . . ?
C9 C10 C18 O2B 177.5(12) . . . . ?
C11 C10 C18 O2B -2.0(12) . . . . ?
C1 C2 C19 O3 178.9(3) . . . . ?
C3 C2 C19 O3 -2.7(4) . . . . ?
C10 C9 N1 C8 -5.9(4) . . . . ?
C10 C9 N1 C1 -175.4(2) . . . . ?
C7 C8 N1 C9 7.1(4) . . . . ?
C3 C8 N1 C9 -171.1(2) . . . . ?
C7 C8 N1 C1 178.8(2) . . . . ?
C3 C8 N1 C1 0.6(3) . . . . ?
C2 C1 N1 C9 169.5(3) . . . . ?
C12 C1 N1 C9 -15.4(4) . . . . ?
C2 C1 N1 C8 -0.8(3) . . . . ?
C12 C1 N1 C8 174.3(2) . . . . ?

_refine_diff_density_max         0.397
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.078

