# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_lo3
_database_code_depnum_ccdc_archive 'CCDC 1049585'
_audit_update_record             
;
2015-02-14 deposited with the CCDC.
2015-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18 Br N2 O'
_chemical_formula_weight         430.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   18.750(2)
_cell_length_b                   6.8019(9)
_cell_length_c                   15.436(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.233(7)
_cell_angle_gamma                90.00
_cell_volume                     1963.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             876
_exptl_absorpt_coefficient_mu    2.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.5474
_exptl_absorpt_correction_T_max  0.6015
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7767
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0620
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.73
_diffrn_reflns_theta_max         63.90
_reflns_number_total             3069
_reflns_number_gt                2457
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1065P)²+6.2860P] 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         3069
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0845
_refine_ls_wR_factor_ref         0.2364
_refine_ls_wR_factor_gt          0.2246
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.001

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 -0.3868(5) -0.1338(10) 0.4115(5) 0.076(2) Uani 1 1 d . . .
H1 H -0.3558 -0.2409 0.4147 0.091 Uiso 1 1 calc R . .
C2 C -0.4479(7) -0.1437(15) 0.3582(6) 0.100(3) Uani 1 1 d . . .
H2 H -0.4586 -0.2576 0.3266 0.120 Uiso 1 1 calc R . .
C3 C -0.4934(5) 0.0129(18) 0.3510(5) 0.098(3) Uani 1 1 d . . .
H3 H -0.5347 0.0070 0.3137 0.118 Uiso 1 1 calc R . .
C4 C -0.4775(4) 0.1829(14) 0.4001(5) 0.081(2) Uani 1 1 d . . .
H4 H -0.5086 0.2896 0.3951 0.098 Uiso 1 1 calc R . .
C5 C -0.4166(3) 0.1945(9) 0.4559(4) 0.0572(15) Uani 1 1 d . . .
C6 C -0.4026(4) 0.3730(9) 0.5068(5) 0.0663(18) Uani 1 1 d . . .
H6 H -0.4194 0.4898 0.4815 0.080 Uiso 1 1 calc R . .
C7 C -0.3681(4) 0.3879(9) 0.5863(5) 0.0654(18) Uani 1 1 d . . .
H7 H -0.3626 0.5137 0.6095 0.078 Uiso 1 1 calc R . .
C8 C -0.3388(3) 0.2284(9) 0.6390(4) 0.0567(15) Uani 1 1 d . . .
C9 C -0.3392(4) 0.2432(12) 0.7292(5) 0.075(2) Uani 1 1 d . . .
H9 H -0.3576 0.3565 0.7529 0.090 Uiso 1 1 calc R . .
C10 C -0.3135(5) 0.0976(16) 0.7839(6) 0.089(2) Uani 1 1 d . . .
H10 H -0.3143 0.1126 0.8437 0.107 Uiso 1 1 calc R . .
C11 C -0.2868(4) -0.0703(15) 0.7501(6) 0.089(3) Uani 1 1 d . . .
H11 H -0.2694 -0.1704 0.7868 0.106 Uiso 1 1 calc R . .
C12 C -0.2857(4) -0.0909(10) 0.6607(5) 0.0705(19) Uani 1 1 d . . .
H12 H -0.2685 -0.2067 0.6379 0.085 Uiso 1 1 calc R . .
C13 C -0.3099(3) 0.0583(9) 0.6052(4) 0.0544(15) Uani 1 1 d . . .
N14 N -0.3036(3) 0.0448(7) 0.5131(4) 0.0573(13) Uani 1 1 d . . .
C15 C -0.3694(4) 0.0325(9) 0.4614(4) 0.0570(16) Uani 1 1 d . . .
C16 C -0.2437(5) -0.0792(10) 0.4888(7) 0.094(3) Uani 1 1 d . . .
H16 H -0.2339 -0.1978 0.5172 0.113 Uiso 1 1 calc R . .
C17 C -0.2054(6) -0.0221(13) 0.4285(13) 0.208(9) Uani 1 1 d . . .
H17 H -0.2399 -0.0140 0.3777 0.249 Uiso 1 1 calc R . .
O18 O -0.1568(4) -0.1799(8) 0.4048(6) 0.148(4) Uani 1 1 d . . .
N19 N -0.0902(4) -0.0977(8) 0.3881(6) 0.101(3) Uani 1 1 d . . .
C20 C -0.0932(4) 0.0889(9) 0.3971(5) 0.0655(18) Uani 1 1 d . . .
C21 C -0.1630(4) 0.1649(10) 0.4229(6) 0.084(2) Uani 1 1 d . . .
H21A H -0.1849 0.2534 0.3795 0.101 Uiso 1 1 calc R . .
H21B H -0.1578 0.2318 0.4785 0.101 Uiso 1 1 calc R . .
C22 C -0.0315(3) 0.2116(9) 0.3775(4) 0.0513(14) Uani 1 1 d . . .
C23 C 0.0277(3) 0.1286(9) 0.3407(4) 0.0587(16) Uani 1 1 d . . .
H23 H 0.0278 -0.0047 0.3273 0.070 Uiso 1 1 calc R . .
C24 C 0.0853(3) 0.2430(10) 0.3242(4) 0.0620(16) Uani 1 1 d . . .
H24 H 0.1240 0.1884 0.2984 0.074 Uiso 1 1 calc R . .
C25 C 0.0856(3) 0.4404(10) 0.3462(4) 0.0595(16) Uani 1 1 d . . .
C26 C 0.0279(4) 0.5248(10) 0.3797(5) 0.0666(17) Uani 1 1 d . . .
H26 H 0.0278 0.6587 0.3919 0.080 Uiso 1 1 calc R . .
C27 C -0.0303(4) 0.4111(9) 0.3951(4) 0.0606(16) Uani 1 1 d . . .
H27 H -0.0697 0.4693 0.4179 0.073 Uiso 1 1 calc R . .
Br28 Br 0.16770(4) 0.59482(13) 0.32819(7) 0.0905(4) 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 1.362(13) . ?
C1 C15 1.393(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(15) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(10) . ?
C4 H4 0.9300 . ?
C5 C15 1.411(9) . ?
C5 C6 1.459(10) . ?
C6 C7 1.349(11) . ?
C6 H6 0.9300 . ?
C7 C8 1.441(9) . ?
C7 H7 0.9300 . ?
C8 C13 1.395(9) . ?
C8 C9 1.396(10) . ?
C9 C10 1.366(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.366(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.383(9) . ?
C12 H12 0.9300 . ?
C13 N14 1.439(8) . ?
N14 C15 1.423(9) . ?
N14 C16 1.474(8) . ?
C16 C17 1.278(15) . ?
C16 H16 0.9300 . ?
C17 O18 1.471(10) . ?
C17 C21 1.505(11) . ?
C17 H17 0.9800 . ?
O18 N19 1.410(8) . ?
N19 C20 1.279(8) . ?
C20 C22 1.476(9) . ?
C20 C21 1.490(9) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C27 1.384(8) . ?
C22 C23 1.402(9) . ?
C23 C24 1.370(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(9) . ?
C24 H24 0.9300 . ?
C25 C26 1.361(9) . ?
C25 Br28 1.900(6) . ?
C26 C27 1.372(9) . ?
C26 H26 0.9300 . ?
C27 H27 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 C15 121.7(8) . . ?
C2 C1 H1 119.2 . . ?
C15 C1 H1 119.2 . . ?
C1 C2 C3 120.3(8) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 119.5(8) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 121.1(9) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C15 118.6(7) . . ?
C4 C5 C6 119.3(7) . . ?
C15 C5 C6 122.1(6) . . ?
C7 C6 C5 127.4(6) . . ?
C7 C6 H6 116.3 . . ?
C5 C6 H6 116.3 . . ?
C6 C7 C8 126.5(6) . . ?
C6 C7 H7 116.8 . . ?
C8 C7 H7 116.8 . . ?
C13 C8 C9 117.6(6) . . ?
C13 C8 C7 123.8(6) . . ?
C9 C8 C7 118.6(6) . . ?
C10 C9 C8 122.4(8) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C11 C10 C9 119.5(9) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.8(8) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.9(7) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 119.7(7) . . ?
C12 C13 N14 121.2(6) . . ?
C8 C13 N14 119.0(5) . . ?
C15 N14 C13 115.3(5) . . ?
C15 N14 C16 118.0(6) . . ?
C13 N14 C16 114.0(6) . . ?
C1 C15 C5 118.8(7) . . ?
C1 C15 N14 121.0(6) . . ?
C5 C15 N14 120.1(5) . . ?
C17 C16 N14 119.4(8) . . ?
C17 C16 H16 120.3 . . ?
N14 C16 H16 120.3 . . ?
C16 C17 O18 110.6(10) . . ?
C16 C17 C21 128.7(13) . . ?
O18 C17 C21 105.3(6) . . ?
C16 C17 H17 103.1 . . ?
O18 C17 H17 103.1 . . ?
C21 C17 H17 103.1 . . ?
N19 O18 C17 109.2(6) . . ?
C20 N19 O18 109.1(6) . . ?
N19 C20 C22 119.9(6) . . ?
N19 C20 C21 114.8(6) . . ?
C22 C20 C21 125.3(6) . . ?
C20 C21 C17 101.5(6) . . ?
C20 C21 H21A 111.5 . . ?
C17 C21 H21A 111.5 . . ?
C20 C21 H21B 111.5 . . ?
C17 C21 H21B 111.5 . . ?
H21A C21 H21B 109.3 . . ?
C27 C22 C23 118.2(6) . . ?
C27 C22 C20 121.0(6) . . ?
C23 C22 C20 120.8(6) . . ?
C24 C23 C22 120.3(6) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.6(6) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.9(6) . . ?
C26 C25 Br28 119.9(5) . . ?
C24 C25 Br28 119.2(5) . . ?
C25 C26 C27 119.5(6) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 H26 120.2 . . ?
C26 C27 C22 121.4(6) . . ?
C26 C27 H27 119.3 . . ?
C22 C27 H27 119.3 . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        63.90
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.821
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.091
