# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_201512164
_database_code_depnum_ccdc_archive 'CCDC 1447043'
_audit_update_record             
;
2016-01-13 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
_audit_creation_date             2015-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H9 Br O2'
_chemical_formula_sum            'C15 H9 Br O2'
_chemical_formula_weight         301.13
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N3O2Br1
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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.1904(13)
_cell_length_b                   3.9703(3)
_cell_length_c                   25.5341(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1235.85(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1278
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      22.9620
_cell_measurement_theta_min      4.0980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.315
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.618
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0711
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            7951
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.369
_diffrn_reflns_theta_min         3.342
_diffrn_ambient_temperature      291.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -33.00   0.50    7.50    --  -14.59 127.00   5.00   50
  2  ω    -67.00 -42.00   0.50    7.50    --  -14.59 142.00 176.00   50
  3  ω     20.00  45.00   0.50    7.50    --   17.71-142.00 120.00   50
  4  ω     11.00  36.00   0.50    7.50    --   17.71-127.00 -69.00   50
  5  ω    -69.00 -42.00   0.50    7.50    --  -14.59-178.00  30.00   54
  6  ω      3.00  73.00   0.50    7.50    --   17.71  57.00-120.00  140
  7  ω      6.00  71.00   0.50    7.50    --   17.71  57.00 -60.00  130
  8  ω      5.00  85.00   0.50    7.50    --   17.71  57.00 150.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0300850000
_diffrn_orient_matrix_UB_12      -0.0197876000
_diffrn_orient_matrix_UB_13      -0.0235776000
_diffrn_orient_matrix_UB_21      0.0492317000
_diffrn_orient_matrix_UB_22      -0.0142137000
_diffrn_orient_matrix_UB_23      0.0146084000
_diffrn_orient_matrix_UB_31      -0.0073315000
_diffrn_orient_matrix_UB_32      -0.1770810000
_diffrn_orient_matrix_UB_33      0.0014631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.941
_reflns_Friedel_fraction_max     0.938
_reflns_number_gt                1694
_reflns_number_total             2420
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 574 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.023(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2420
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0392P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.1051
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C11(H11), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.54595(9) 1.27592(19) 0.24686(7) 0.0953(4) Uani 1 1 d . . . . .
C1 C 0.5640(7) 0.3698(19) 0.5872(3) 0.0556(19) Uani 1 1 d . . . . .
H1 H 0.4946 0.3040 0.5761 0.067 Uiso 1 1 calc R . . . .
C2 C 0.5981(8) 0.300(2) 0.6371(3) 0.067(2) Uani 1 1 d . . . . .
H2 H 0.5503 0.1929 0.6600 0.080 Uiso 1 1 calc R . . . .
C3 C 0.7023(9) 0.387(2) 0.6541(4) 0.073(3) Uani 1 1 d . . . . .
H3 H 0.7246 0.3313 0.6879 0.087 Uiso 1 1 calc R . . . .
C4 C 0.7729(7) 0.555(2) 0.6210(3) 0.061(2) Uani 1 1 d . . . . .
H4 H 0.8424 0.6172 0.6324 0.073 Uiso 1 1 calc R . . . .
C5 C 0.7388(6) 0.6284(17) 0.5707(3) 0.0452(17) Uani 1 1 d . . . . .
C6 C 0.6342(6) 0.5404(17) 0.5529(2) 0.0440(17) Uani 1 1 d . . . . .
C7 C 0.6073(5) 0.6329(16) 0.5003(3) 0.0427(16) Uani 1 1 d . . . . .
H7 H 0.5387 0.5720 0.4874 0.051 Uiso 1 1 calc R . . . .
C8 C 0.6754(5) 0.8029(15) 0.4683(3) 0.0392(16) Uani 1 1 d . . . . .
C9 C 0.7814(6) 0.9078(19) 0.4898(3) 0.0470(18) Uani 1 1 d . . . . .
C10 C 0.6457(5) 0.9067(15) 0.4144(3) 0.0415(15) Uani 1 1 d . . . . .
C11 C 0.7209(6) 0.906(2) 0.3738(3) 0.0524(19) Uani 1 1 d . . . . .
H11 H 0.7924 0.8365 0.3803 0.063 Uiso 1 1 calc R . . . .
C12 C 0.6922(7) 1.005(2) 0.3237(3) 0.065(2) Uani 1 1 d . . . . .
H12 H 0.7432 0.9972 0.2966 0.078 Uiso 1 1 calc R . . . .
C13 C 0.5872(7) 1.1144(19) 0.3147(3) 0.059(2) Uani 1 1 d . . . . .
C14 C 0.5106(6) 1.1186(18) 0.3539(3) 0.0561(19) Uani 1 1 d . . . . .
H14 H 0.4394 1.1905 0.3472 0.067 Uiso 1 1 calc R . . . .
C15 C 0.5403(5) 1.0144(17) 0.4037(3) 0.0478(17) Uani 1 1 d . . . . .
H15 H 0.4884 1.0171 0.4304 0.057 Uiso 1 1 calc R . . . .
O1 O 0.8102(3) 0.8044(11) 0.5390(2) 0.0506(13) Uani 1 1 d . . . . .
O2 O 0.8488(4) 1.0810(15) 0.4668(2) 0.0634(14) 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
Br1 C13 1.915(8) . ?
C1 H1 0.9300 . ?
C1 C2 1.369(11) . ?
C1 C6 1.398(10) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(13) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(10) . ?
C5 C6 1.399(10) . ?
C5 O1 1.377(9) . ?
C6 C7 1.431(9) . ?
C7 H7 0.9300 . ?
C7 C8 1.346(9) . ?
C8 C9 1.464(9) . ?
C8 C10 1.482(10) . ?
C9 O1 1.369(9) . ?
C9 O2 1.221(8) . ?
C10 C11 1.384(9) . ?
C10 C15 1.381(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.382(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(11) . ?
C13 C14 1.370(11) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(10) . ?
C15 H15 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
C2 C1 H1 120.2 . . ?
C2 C1 C6 119.7(8) . . ?
C6 C1 H1 120.2 . . ?
C1 C2 H2 119.3 . . ?
C1 C2 C3 121.4(9) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(9) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(8) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 C6 121.5(7) . . ?
O1 C5 C4 117.6(7) . . ?
O1 C5 C6 120.9(6) . . ?
C1 C6 C5 118.4(6) . . ?
C1 C6 C7 124.9(7) . . ?
C5 C6 C7 116.7(6) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 C6 123.8(7) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 C9 117.4(7) . . ?
C7 C8 C10 123.5(6) . . ?
C9 C8 C10 119.0(6) . . ?
O1 C9 C8 119.0(6) . . ?
O2 C9 C8 125.1(7) . . ?
O2 C9 O1 115.9(6) . . ?
C11 C10 C8 122.2(6) . . ?
C15 C10 C8 119.8(6) . . ?
C15 C10 C11 118.0(6) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.7(7) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.6 . . ?
C13 C12 C11 118.7(7) . . ?
C13 C12 H12 120.6 . . ?
C12 C13 Br1 120.2(7) . . ?
C14 C13 Br1 118.6(6) . . ?
C14 C13 C12 121.2(7) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.3(7) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 121.1(6) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C9 O1 C5 121.9(5) . . ?

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 C13 C14 C15 -177.6(5) . . . . ?
C1 C2 C3 C4 1.9(12) . . . . ?
C1 C6 C7 C8 178.7(7) . . . . ?
C2 C1 C6 C5 1.4(10) . . . . ?
C2 C1 C6 C7 -178.7(7) . . . . ?
C2 C3 C4 C5 -1.3(12) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?
C3 C4 C5 O1 178.3(7) . . . . ?
C4 C5 C6 C1 -0.9(10) . . . . ?
C4 C5 C6 C7 179.3(7) . . . . ?
C4 C5 O1 C9 -175.8(6) . . . . ?
C5 C6 C7 C8 -1.5(10) . . . . ?
C6 C1 C2 C3 -1.9(11) . . . . ?
C6 C5 O1 C9 1.7(9) . . . . ?
C6 C7 C8 C9 -2.2(9) . . . . ?
C6 C7 C8 C10 -178.1(6) . . . . ?
C7 C8 C9 O1 5.7(9) . . . . ?
C7 C8 C9 O2 -175.2(7) . . . . ?
C7 C8 C10 C11 -143.5(7) . . . . ?
C7 C8 C10 C15 37.6(9) . . . . ?
C8 C9 O1 C5 -5.5(9) . . . . ?
C8 C10 C11 C12 -179.7(7) . . . . ?
C8 C10 C15 C14 178.9(6) . . . . ?
C9 C8 C10 C11 40.7(9) . . . . ?
C9 C8 C10 C15 -138.2(6) . . . . ?
C10 C8 C9 O1 -178.3(5) . . . . ?
C10 C8 C9 O2 0.9(10) . . . . ?
C10 C11 C12 C13 1.6(12) . . . . ?
C11 C10 C15 C14 -0.1(10) . . . . ?
C11 C12 C13 Br1 176.8(6) . . . . ?
C11 C12 C13 C14 -1.7(12) . . . . ?
C12 C13 C14 C15 0.9(11) . . . . ?
C13 C14 C15 C10 0.0(11) . . . . ?
C15 C10 C11 C12 -0.8(11) . . . . ?
O1 C5 C6 C1 -178.3(6) . . . . ?
O1 C5 C6 C7 1.9(9) . . . . ?
O2 C9 O1 C5 175.3(6) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.813
