# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_txf
_audit_block_doi                 10.5517/ccdc.csd.cc1nlvy1
_database_code_depnum_ccdc_archive 'CCDC 1537474'
_audit_update_record             
;
2017-03-12 deposited with the CCDC.
2017-04-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H17 Br N2 O3'
_chemical_formula_weight         425.28

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'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.869(2)
_cell_length_b                   14.380(3)
_cell_length_c                   10.957(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.813(4)
_cell_angle_gamma                90.00
_cell_volume                     1919.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3378
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.29

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_T_max  0.6966
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10887
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_sigmaI/netI    0.0757
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3567
_reflns_number_gt                2486
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3567
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.26211(3) 0.12888(3) 0.61701(4) 0.0662(2) Uani 1 1 d . . .
N2 N 0.8298(3) 0.0213(3) 0.8009(4) 0.0717(10) Uani 1 1 d . . .
N1 N 0.9848(2) 0.2398(3) 0.5885(4) 0.0687(10) Uani 1 1 d . . .
O1 O 0.68009(19) 0.14472(17) 0.3714(2) 0.0465(6) Uani 1 1 d . . .
O3 O 0.5508(2) 0.11730(16) 0.1224(2) 0.0529(7) Uani 1 1 d . . .
O2 O 0.6370(3) 0.1482(2) -0.0216(3) 0.0736(9) Uani 1 1 d . . .
C19 C 0.3958(3) 0.1283(2) 0.5773(3) 0.0422(8) Uani 1 1 d . . .
C16 C 0.5928(3) 0.1250(2) 0.5268(3) 0.0349(7) Uani 1 1 d . . .
C9 C 0.6959(3) 0.1200(2) 0.4975(3) 0.0377(7) Uani 1 1 d . . .
C17 C 0.4941(3) 0.1135(2) 0.4274(3) 0.0402(8) Uani 1 1 d . . .
H17 H 0.4945 0.1047 0.3434 0.048 Uiso 1 1 calc R . .
C18 C 0.3948(3) 0.1150(2) 0.4526(3) 0.0437(8) Uani 1 1 d . . .
H18 H 0.3288 0.1071 0.3862 0.052 Uiso 1 1 calc R . .
C21 C 0.5907(3) 0.1415(2) 0.6514(3) 0.0428(8) Uani 1 1 d . . .
H21 H 0.6561 0.1514 0.7181 0.051 Uiso 1 1 calc R . .
C20 C 0.4926(3) 0.1431(2) 0.6763(3) 0.0466(8) Uani 1 1 d . . .
H20 H 0.4915 0.1542 0.7595 0.056 Uiso 1 1 calc R . .
C12 C 0.6400(4) 0.1342(2) 0.0888(4) 0.0518(9) Uani 1 1 d . . .
C2 C 1.0603(4) 0.1498(4) 0.7558(5) 0.0784(14) Uani 1 1 d . . .
H2 H 1.0785 0.0983 0.8100 0.094 Uiso 1 1 calc R . .
C6 C 0.8776(3) 0.1531(3) 0.4151(4) 0.0521(9) Uani 1 1 d . . .
H6 H 0.9305 0.1342 0.3725 0.063 Uiso 1 1 calc R . .
C11 C 0.7440(4) 0.1359(2) 0.1939(4) 0.0537(10) Uani 1 1 d . . .
H11 H 0.8060 0.1331 0.1680 0.064 Uiso 1 1 calc R . .
C8 C 0.7955(3) 0.0923(2) 0.5761(3) 0.0411(7) Uani 1 1 d . . .
C15 C 0.8099(3) 0.0541(3) 0.7014(4) 0.0481(8) Uani 1 1 d . . .
C10 C 0.7651(3) 0.1407(2) 0.3214(4) 0.0467(9) Uani 1 1 d . . .
C7 C 0.8998(3) 0.0953(3) 0.5386(3) 0.0501(9) Uani 1 1 d . . .
H7 H 0.9265 0.0328 0.5288 0.060 Uiso 1 1 calc R . .
C13 C 0.4467(4) 0.1199(3) 0.0169(4) 0.0562(10) Uani 1 1 d . . .
H13A H 0.4467 0.0737 -0.0477 0.067 Uiso 1 1 calc R . .
H13B H 0.4359 0.1807 -0.0236 0.067 Uiso 1 1 calc R . .
C5 C 0.9033(3) 0.2540(3) 0.4613(4) 0.0656(11) Uani 1 1 d . . .
H5A H 0.9335 0.2889 0.4049 0.079 Uiso 1 1 calc R . .
H5B H 0.8386 0.2856 0.4674 0.079 Uiso 1 1 calc R . .
C1 C 0.9864(3) 0.1528(4) 0.6340(4) 0.0616(11) Uani 1 1 d . . .
C14 C 0.3576(4) 0.0999(4) 0.0719(5) 0.0765(13) Uani 1 1 d . . .
H14A H 0.3723 0.0419 0.1178 0.115 Uiso 1 1 calc R . .
H14B H 0.2888 0.0959 0.0034 0.115 Uiso 1 1 calc R . .
H14C H 0.3541 0.1489 0.1299 0.115 Uiso 1 1 calc R . .
C3 C 1.1031(4) 0.2402(5) 0.7827(6) 0.101(2) Uani 1 1 d . . .
H3 H 1.1555 0.2592 0.8590 0.122 Uiso 1 1 calc R . .
C4 C 1.0556(4) 0.2950(4) 0.6795(6) 0.0934(18) Uani 1 1 d . . .
H4 H 1.0686 0.3580 0.6720 0.112 Uiso 1 1 calc R . .


_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 C19 1.906(3) . ?
N2 C15 1.138(5) . ?
N1 C1 1.344(6) . ?
N1 C4 1.366(6) . ?
N1 C5 1.464(5) . ?
O1 C10 1.373(4) . ?
O1 C9 1.377(4) . ?
O3 C12 1.337(5) . ?
O3 C13 1.460(5) . ?
O2 C12 1.214(5) . ?
C19 C18 1.376(5) . ?
C19 C20 1.379(5) . ?
C16 C17 1.391(4) . ?
C16 C21 1.394(5) . ?
C16 C9 1.464(5) . ?
C9 C8 1.353(5) . ?
C17 C18 1.393(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C21 C20 1.376(5) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C12 C11 1.457(6) . ?
C2 C1 1.367(6) . ?
C2 C3 1.405(8) . ?
C2 H2 0.9300 . ?
C6 C10 1.491(5) . ?
C6 C7 1.534(5) . ?
C6 C5 1.537(5) . ?
C6 H6 0.9800 . ?
C11 C10 1.336(5) . ?
C11 H11 0.9300 . ?
C8 C15 1.435(5) . ?
C8 C7 1.526(4) . ?
C7 C1 1.505(6) . ?
C7 H7 0.9800 . ?
C13 C14 1.485(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C3 C4 1.351(8) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?

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
C1 N1 C4 110.1(5) . . ?
C1 N1 C5 113.8(3) . . ?
C4 N1 C5 135.9(5) . . ?
C10 O1 C9 120.7(3) . . ?
C12 O3 C13 115.3(3) . . ?
C18 C19 C20 121.3(3) . . ?
C18 C19 Br1 120.4(3) . . ?
C20 C19 Br1 118.2(3) . . ?
C17 C16 C21 119.2(3) . . ?
C17 C16 C9 119.0(3) . . ?
C21 C16 C9 121.8(3) . . ?
C8 C9 O1 121.1(3) . . ?
C8 C9 C16 127.9(3) . . ?
O1 C9 C16 110.9(3) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 118.9(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C21 C16 120.3(3) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O2 C12 O3 123.4(4) . . ?
O2 C12 C11 120.7(4) . . ?
O3 C12 C11 115.9(3) . . ?
C1 C2 C3 106.1(5) . . ?
C1 C2 H2 126.9 . . ?
C3 C2 H2 126.9 . . ?
C10 C6 C7 113.9(3) . . ?
C10 C6 C5 113.4(3) . . ?
C7 C6 C5 105.1(3) . . ?
C10 C6 H6 108.0 . . ?
C7 C6 H6 108.0 . . ?
C5 C6 H6 108.0 . . ?
C10 C11 C12 130.7(4) . . ?
C10 C11 H11 114.6 . . ?
C12 C11 H11 114.6 . . ?
C9 C8 C15 121.6(3) . . ?
C9 C8 C7 123.8(3) . . ?
C15 C8 C7 114.6(3) . . ?
N2 C15 C8 174.2(4) . . ?
C11 C10 O1 120.0(4) . . ?
C11 C10 C6 123.4(3) . . ?
O1 C10 C6 116.2(3) . . ?
C1 C7 C8 110.3(3) . . ?
C1 C7 C6 101.6(3) . . ?
C8 C7 C6 108.8(3) . . ?
C1 C7 H7 111.9 . . ?
C8 C7 H7 111.9 . . ?
C6 C7 H7 111.9 . . ?
O3 C13 C14 107.8(3) . . ?
O3 C13 H13A 110.2 . . ?
C14 C13 H13A 110.2 . . ?
O3 C13 H13B 110.2 . . ?
C14 C13 H13B 110.2 . . ?
H13A C13 H13B 108.5 . . ?
N1 C5 C6 101.2(3) . . ?
N1 C5 H5A 111.5 . . ?
C6 C5 H5A 111.5 . . ?
N1 C5 H5B 111.5 . . ?
C6 C5 H5B 111.5 . . ?
H5A C5 H5B 109.3 . . ?
N1 C1 C2 108.3(4) . . ?
N1 C1 C7 109.5(4) . . ?
C2 C1 C7 141.9(5) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C3 C2 108.9(5) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
C3 C4 N1 106.7(5) . . ?
C3 C4 H4 126.7 . . ?
N1 C4 H4 126.7 . . ?

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
C10 O1 C9 C8 0.9(4) . . . . ?
C10 O1 C9 C16 -176.9(3) . . . . ?
C17 C16 C9 C8 -151.0(3) . . . . ?
C21 C16 C9 C8 29.3(5) . . . . ?
C17 C16 C9 O1 26.6(4) . . . . ?
C21 C16 C9 O1 -153.1(3) . . . . ?
C21 C16 C17 C18 -2.3(5) . . . . ?
C9 C16 C17 C18 178.0(3) . . . . ?
C20 C19 C18 C17 2.1(5) . . . . ?
Br1 C19 C18 C17 -179.0(2) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C16 C21 C20 2.2(5) . . . . ?
C9 C16 C21 C20 -178.1(3) . . . . ?
C16 C21 C20 C19 0.1(5) . . . . ?
C18 C19 C20 C21 -2.3(5) . . . . ?
Br1 C19 C20 C21 178.8(3) . . . . ?
C13 O3 C12 O2 -2.1(5) . . . . ?
C13 O3 C12 C11 177.4(3) . . . . ?
O2 C12 C11 C10 165.2(4) . . . . ?
O3 C12 C11 C10 -14.4(5) . . . . ?
O1 C9 C8 C15 -171.1(3) . . . . ?
C16 C9 C8 C15 6.3(5) . . . . ?
O1 C9 C8 C7 6.5(5) . . . . ?
C16 C9 C8 C7 -176.0(3) . . . . ?
C9 C8 C15 N2 166(4) . . . . ?
C7 C8 C15 N2 -12(4) . . . . ?
C12 C11 C10 O1 0.3(6) . . . . ?
C12 C11 C10 C6 -172.4(4) . . . . ?
C9 O1 C10 C11 158.9(3) . . . . ?
C9 O1 C10 C6 -27.9(4) . . . . ?
C7 C6 C10 C11 -140.4(3) . . . . ?
C5 C6 C10 C11 99.3(4) . . . . ?
C7 C6 C10 O1 46.7(4) . . . . ?
C5 C6 C10 O1 -73.6(4) . . . . ?
C9 C8 C7 C1 123.0(4) . . . . ?
C15 C8 C7 C1 -59.2(4) . . . . ?
C9 C8 C7 C6 12.3(5) . . . . ?
C15 C8 C7 C6 -169.9(3) . . . . ?
C10 C6 C7 C1 -153.2(3) . . . . ?
C5 C6 C7 C1 -28.4(4) . . . . ?
C10 C6 C7 C8 -36.8(4) . . . . ?
C5 C6 C7 C8 88.0(3) . . . . ?
C12 O3 C13 C14 -179.9(3) . . . . ?
C1 N1 C5 C6 -17.0(4) . . . . ?
C4 N1 C5 C6 169.4(4) . . . . ?
C10 C6 C5 N1 152.8(3) . . . . ?
C7 C6 C5 N1 27.6(4) . . . . ?
C4 N1 C1 C2 -1.0(5) . . . . ?
C5 N1 C1 C2 -176.2(3) . . . . ?
C4 N1 C1 C7 174.2(3) . . . . ?
C5 N1 C1 C7 -1.1(4) . . . . ?
C3 C2 C1 N1 0.5(5) . . . . ?
C3 C2 C1 C7 -172.0(5) . . . . ?
C8 C7 C1 N1 -96.6(4) . . . . ?
C6 C7 C1 N1 18.7(4) . . . . ?
C8 C7 C1 C2 75.9(6) . . . . ?
C6 C7 C1 C2 -168.8(5) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C2 C3 C4 N1 -0.6(5) . . . . ?
C1 N1 C4 C3 1.0(5) . . . . ?
C5 N1 C4 C3 174.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.778
_refine_diff_density_rms         0.106
