# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014


data_pr-87

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H14 Br N O'
_chemical_formula_weight         376.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3715(4)
_cell_length_b                   9.3781(7)
_cell_length_c                   12.8371(12)
_cell_angle_alpha                96.360(7)
_cell_angle_beta                 99.202(7)
_cell_angle_gamma                111.905(6)
_cell_volume                     798.57(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    183(2)
_cell_measurement_reflns_used    3303
_cell_measurement_theta_min      3.0269
_cell_measurement_theta_max      29.0973

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    2.580
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87895
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      183(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9853
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10852
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0571
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         26.01
_reflns_number_total             3147
_reflns_number_gt                2630
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis RED (Oxford, 2011)'
_computing_cell_refinement       'CrysAlis RED (Oxford, 2011)'
_computing_data_reduction        'CrysAlis RED (Oxford, 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1370P)²+1.2643P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3147
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0759
_refine_ls_wR_factor_ref         0.2198
_refine_ls_wR_factor_gt          0.2085
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.097
_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
C1 C 0.5721(8) 0.2521(6) 0.7785(5) 0.0235(12) Uani 1 1 d . . .
C2 C 0.5651(9) 0.3807(7) 0.7356(5) 0.0300(13) Uani 1 1 d . . .
H2 H 0.6145 0.4797 0.7817 0.036 Uiso 1 1 calc R . .
C3 C 0.4902(9) 0.3686(7) 0.6304(5) 0.0294(13) Uani 1 1 d . . .
H3 H 0.4894 0.4582 0.6027 0.035 Uiso 1 1 calc R . .
C4 C 0.4142(9) 0.2229(7) 0.5633(5) 0.0260(12) Uani 1 1 d . . .
C5 C 0.4163(9) 0.0915(7) 0.6012(5) 0.0285(13) Uani 1 1 d . . .
H5 H 0.3628 -0.0074 0.5547 0.034 Uiso 1 1 calc R . .
C6 C 0.4980(9) 0.1073(7) 0.7086(5) 0.0276(12) Uani 1 1 d . . .
H6 H 0.5043 0.0185 0.7355 0.033 Uiso 1 1 calc R . .
C7 C 0.7852(8) 0.3781(7) 1.0813(4) 0.0221(11) Uani 1 1 d . . .
C8 C 0.7051(8) 0.3872(7) 0.9727(5) 0.0242(12) Uani 1 1 d . . .
C9 C 0.6549(8) 0.2649(6) 0.8923(4) 0.0214(11) Uani 1 1 d . . .
C11 C 0.7483(8) 0.1146(7) 1.0125(4) 0.0238(12) Uani 1 1 d . . .
C12 C 0.8019(8) 0.2437(6) 1.1011(4) 0.0226(11) Uani 1 1 d . . .
C13 C 0.8535(8) 0.5128(7) 1.1699(4) 0.0237(12) Uani 1 1 d . . .
C14 C 0.8966(8) 0.6650(7) 1.1513(5) 0.0270(12) Uani 1 1 d . . .
H14 H 0.8752 0.6825 1.0797 0.032 Uiso 1 1 calc R . .
C15 C 0.9700(9) 0.7905(8) 1.2361(5) 0.0339(14) Uani 1 1 d . . .
H15 H 1.0017 0.8937 1.2228 0.041 Uiso 1 1 calc R . .
C16 C 0.9968(9) 0.7645(8) 1.3405(5) 0.0343(14) Uani 1 1 d . . .
H16 H 1.0440 0.8501 1.3989 0.041 Uiso 1 1 calc R . .
C17 C 0.9557(9) 0.6160(7) 1.3601(5) 0.0298(13) Uani 1 1 d . . .
H17 H 0.9775 0.6002 1.4321 0.036 Uiso 1 1 calc R . .
C18 C 0.8829(9) 0.4887(7) 1.2765(4) 0.0267(12) Uani 1 1 d . . .
C19 C 0.7633(9) -0.0246(7) 1.0189(5) 0.0281(13) Uani 1 1 d . . .
C20 C 0.7167(8) -0.1392(7) 0.9272(5) 0.0270(12) Uani 1 1 d . . .
C21 C 0.8821(9) 0.2273(7) 1.2123(5) 0.0291(13) Uani 1 1 d . . .
H21A H 1.0295 0.2626 1.2249 0.035 Uiso 1 1 calc R . .
H21B H 0.8248 0.1160 1.2192 0.035 Uiso 1 1 calc R . .
C22 C 0.8285(11) 0.3247(8) 1.2962(5) 0.0337(14) Uani 1 1 d . . .
H22A H 0.6830 0.2755 1.2935 0.040 Uiso 1 1 calc R . .
H22B H 0.9009 0.3270 1.3687 0.040 Uiso 1 1 calc R . .
N1 N 0.6805(8) -0.2353(6) 0.8531(5) 0.0362(13) Uani 1 1 d . . .
O1 O 0.6785(6) 0.1321(4) 0.9118(3) 0.0238(8) Uani 1 1 d . . .
Br1 Br 0.30917(10) 0.20588(7) 0.41434(5) 0.0400(3) Uani 1 1 d . . .
H8A H 0.677(8) 0.478(7) 0.954(5) 0.015(14) Uiso 1 1 d . . .
H19A H 0.826(11) -0.028(9) 1.077(6) 0.04(2) 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
C1 C2 1.395(8) . ?
C1 C6 1.403(8) . ?
C1 C9 1.464(8) . ?
C2 C3 1.349(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 Br1 1.910(6) . ?
C5 C6 1.381(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C12 1.359(8) . ?
C7 C8 1.449(8) . ?
C7 C13 1.472(7) . ?
C8 C9 1.347(8) . ?
C8 H8A 0.99(6) . ?
C9 O1 1.365(7) . ?
C11 C19 1.361(8) . ?
C11 O1 1.363(7) . ?
C11 C12 1.452(8) . ?
C12 C21 1.502(8) . ?
C13 C14 1.398(8) . ?
C13 C18 1.407(8) . ?
C14 C15 1.384(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.371(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(8) . ?
C17 H17 0.9500 . ?
C18 C22 1.500(9) . ?
C19 C20 1.405(8) . ?
C19 H19A 0.82(8) . ?
C20 N1 1.157(8) . ?
C21 C22 1.529(8) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?

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 C6 117.8(5) . . ?
C2 C1 C9 122.1(5) . . ?
C6 C1 C9 120.0(5) . . ?
C3 C2 C1 121.9(6) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C2 C3 C4 119.0(6) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C5 C4 C3 121.7(5) . . ?
C5 C4 Br1 119.3(4) . . ?
C3 C4 Br1 119.0(4) . . ?
C4 C5 C6 118.3(5) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 121.2(5) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C12 C7 C8 119.2(5) . . ?
C12 C7 C13 119.4(5) . . ?
C8 C7 C13 121.3(5) . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8A 117(3) . . ?
C7 C8 H8A 123(3) . . ?
C8 C9 O1 120.8(5) . . ?
C8 C9 C1 127.7(5) . . ?
O1 C9 C1 111.5(4) . . ?
C19 C11 O1 115.3(5) . . ?
C19 C11 C12 126.3(5) . . ?
O1 C11 C12 118.3(5) . . ?
C7 C12 C11 119.5(5) . . ?
C7 C12 C21 121.5(5) . . ?
C11 C12 C21 119.0(5) . . ?
C14 C13 C18 118.9(5) . . ?
C14 C13 C7 122.0(5) . . ?
C18 C13 C7 119.1(5) . . ?
C15 C14 C13 120.7(6) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 119.6(6) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.4(6) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 121.0(6) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C13 119.3(6) . . ?
C17 C18 C22 121.9(5) . . ?
C13 C18 C22 118.8(5) . . ?
C11 C19 C20 121.8(6) . . ?
C11 C19 H19A 115(5) . . ?
C20 C19 H19A 122(5) . . ?
N1 C20 C19 178.4(7) . . ?
C12 C21 C22 110.4(5) . . ?
C12 C21 H21A 109.6 . . ?
C22 C21 H21A 109.6 . . ?
C12 C21 H21B 109.6 . . ?
C22 C21 H21B 109.6 . . ?
H21A C21 H21B 108.1 . . ?
C18 C22 C21 111.0(5) . . ?
C18 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C18 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C11 O1 C9 122.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.747
_refine_diff_density_min         -0.575
_refine_diff_density_rms         0.172
_database_code_depnum_ccdc_archive 'CCDC 959771'
