# Electronic Supplementary Material (ESI) for ChemComm.
# 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_3t
_database_code_depnum_ccdc_archive 'CCDC 1495970'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_audit_creation_date             2016-04-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H21 Br N2 O4'
_chemical_formula_sum            'C29 H21 Br N2 O4'
_chemical_formula_weight         541.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
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'
O O 0.0492 0.0322 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.08473(14)
_cell_length_b                   16.7619(4)
_cell_length_c                   22.0850(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2622.68(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6583
_cell_measurement_temperature    292.4(3)
_cell_measurement_theta_max      72.1870
_cell_measurement_theta_min      5.2680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.438
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.7
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         5.278
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   53.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega    1.00   75.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -32.00   63.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
  5 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000  -60.0000 84

#__ type_ start__ end____ width___ exp.time_
  6 omega  -31.00   53.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega   39.00  109.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   98.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 58

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   98.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega   38.00   91.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   60.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega   39.00  109.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 15 omega   37.00  144.00   1.0000    6.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -16.0000  -84.0000 107

#__ type_ start__ end____ width___ exp.time_
 16 omega   19.00  103.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 17 omega   17.00  105.00   1.0000    1.1100
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000 -150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0488998000
_diffrn_orient_matrix_UB_12      0.0245742000
_diffrn_orient_matrix_UB_13      -0.0653274000
_diffrn_orient_matrix_UB_21      -0.0027556000
_diffrn_orient_matrix_UB_22      0.0882910000
_diffrn_orient_matrix_UB_23      0.0193673000
_diffrn_orient_matrix_UB_31      0.2119481000
_diffrn_orient_matrix_UB_32      0.0068428000
_diffrn_orient_matrix_UB_33      -0.0148316000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                4641
_reflns_number_total             5097
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.825
_refine_diff_density_min         -1.363
_refine_diff_density_rms         0.120
_refine_ls_abs_structure_details 
;
 Flack x determined using 1737 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.044(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         5097
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1444P)²+1.2789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2136
_refine_ls_wR_factor_ref         0.2211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C00D(H00D), C00O(H00O)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00C(H00C), C00L(H00L), C00M(H00M), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C010(H010)
2.c Idealised Me refined as rotating group:
 C00R(H00B,H00E,H00F), C00Z(H00G,H00H,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br01 Br 0.95197(14) 0.59054(6) 0.46685(7) 0.1122(5) Uani 1 1 d . . . . .
O002 O 0.6223(7) 0.4196(3) 0.33395(18) 0.0618(10) Uani 1 1 d . . . . .
O003 O 0.5008(6) 0.4228(2) 0.50947(16) 0.0546(9) Uani 1 1 d . . . . .
N004 N 0.5015(7) 0.2826(3) 0.5097(2) 0.0529(10) Uani 1 1 d . . . . .
O005 O 0.3131(12) 0.3605(4) 0.2899(3) 0.097(2) Uani 1 1 d . . . . .
O006 O 0.1333(9) 0.4179(4) 0.3606(3) 0.0871(16) Uani 1 1 d . . . . .
C007 C 0.5006(7) 0.2230(3) 0.4676(3) 0.0516(11) Uani 1 1 d . . . . .
C008 C 0.4979(8) 0.2574(4) 0.4089(3) 0.0528(12) Uani 1 1 d . . . . .
C009 C 0.2828(12) 0.3991(4) 0.3417(3) 0.0674(17) Uani 1 1 d . . . . .
C00A C 0.5034(9) 0.1403(4) 0.4755(3) 0.0637(14) Uani 1 1 d . . . . .
H00A H 0.5069 0.1179 0.5141 0.076 Uiso 1 1 calc R . . . .
C00B C 0.4992(8) 0.3529(3) 0.4793(2) 0.0507(11) Uani 1 1 d . . . . .
C00C C 0.4992(9) 0.2083(4) 0.3582(3) 0.0602(14) Uani 1 1 d . . . . .
H00C H 0.5002 0.2298 0.3194 0.072 Uiso 1 1 calc R . . . .
C00D C 0.5762(8) 0.4853(3) 0.4710(2) 0.0504(11) Uani 1 1 d . . . . .
H00D H 0.7078 0.4728 0.4612 0.061 Uiso 1 1 calc R . . . .
C00E C 0.4664(8) 0.4108(3) 0.3769(2) 0.0526(12) Uani 1 1 d . . . . .
C00F C 0.4951(8) 0.3418(3) 0.4177(2) 0.0509(12) Uani 1 1 d . . . . .
C00G C 0.7722(13) 0.5187(5) 0.2737(3) 0.076(2) Uani 1 1 d . . . . .
C00H C 0.6514(10) 0.4978(4) 0.3252(3) 0.0618(15) Uani 1 1 d . . . . .
C00I C 0.5704(10) 0.5617(3) 0.5070(3) 0.0579(14) Uani 1 1 d . . . . .
C00J C 0.7246(14) 0.6129(4) 0.5100(4) 0.079(2) Uani 1 1 d . . . . .
C00K C 0.5561(10) 0.5441(4) 0.3656(3) 0.0574(13) Uani 1 1 d . . . . .
C00L C 0.4991(11) 0.1268(4) 0.3669(4) 0.0739(18) Uani 1 1 d . . . . .
H00L H 0.4977 0.0933 0.3333 0.089 Uiso 1 1 calc R . . . .
C00M C 0.5009(11) 0.0931(4) 0.4248(4) 0.0724(17) Uani 1 1 d . . . . .
H00M H 0.5004 0.0379 0.4290 0.087 Uiso 1 1 calc R . . . .
N00N N 0.5410(19) 0.6961(4) 0.3659(4) 0.109(3) Uani 1 1 d . . . . .
C00O C 0.4618(9) 0.4900(3) 0.4120(2) 0.0512(11) Uani 1 1 d . . . . .
H00O H 0.3317 0.5070 0.4198 0.061 Uiso 1 1 calc R . . . .
C00P C 0.5516(14) 0.6287(4) 0.3661(3) 0.0718(18) Uani 1 1 d . . . . .
C00Q C 0.7545(15) 0.4726(6) 0.2209(3) 0.088(3) Uani 1 1 d . . . . .
H00Q H 0.6665 0.4315 0.2194 0.106 Uiso 1 1 calc R . . . .
C00R C 0.5017(10) 0.2738(4) 0.5757(3) 0.0644(15) Uani 1 1 d . . . . .
H00B H 0.3742 0.2688 0.5899 0.097 Uiso 1 1 calc GR . . . .
H00E H 0.5594 0.3198 0.5938 0.097 Uiso 1 1 calc GR . . . .
H00F H 0.5717 0.2269 0.5867 0.097 Uiso 1 1 calc GR . . . .
C00S C 0.4067(13) 0.5826(5) 0.5373(3) 0.077(2) Uani 1 1 d . . . . .
H00S H 0.3017 0.5495 0.5349 0.093 Uiso 1 1 calc R . . . .
C00T C 0.718(3) 0.6815(5) 0.5441(5) 0.122(5) Uani 1 1 d . . . . .
H00T H 0.8231 0.7145 0.5471 0.146 Uiso 1 1 calc R . . . .
C00U C 0.397(2) 0.6519(6) 0.5711(4) 0.114(5) Uani 1 1 d . . . . .
H00U H 0.2862 0.6650 0.5914 0.137 Uiso 1 1 calc R . . . .
C00V C 0.8966(19) 0.5794(6) 0.2770(5) 0.108(3) Uani 1 1 d . . . . .
H00V H 0.9052 0.6115 0.3113 0.129 Uiso 1 1 calc R . . . .
C00W C 0.866(2) 0.4877(8) 0.1719(4) 0.112(4) Uani 1 1 d . . . . .
H00W H 0.8534 0.4573 0.1369 0.134 Uiso 1 1 calc R . . . .
C00X C 0.997(2) 0.5484(7) 0.1747(5) 0.119(5) Uani 1 1 d . . . . .
H00X H 1.0723 0.5590 0.1413 0.143 Uiso 1 1 calc R . . . .
C00Y C 0.549(3) 0.7008(6) 0.5745(5) 0.138(7) Uani 1 1 d . . . . .
H00Y H 0.5415 0.7475 0.5972 0.165 Uiso 1 1 calc R . . . .
C00Z C 0.142(2) 0.3359(9) 0.2567(6) 0.144(6) Uani 1 1 d . . . . .
H00G H 0.1701 0.2906 0.2318 0.216 Uiso 1 1 calc GR . . . .
H00H H 0.0992 0.3792 0.2317 0.216 Uiso 1 1 calc GR . . . .
H00I H 0.0445 0.3221 0.2851 0.216 Uiso 1 1 calc GR . . . .
C010 C 1.016(2) 0.5924(7) 0.2248(7) 0.133(5) Uani 1 1 d . . . . .
H010 H 1.1080 0.6319 0.2262 0.159 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
Br01 C00J 1.908(11) . ?
O002 C00E 1.463(7) . ?
O002 C00H 1.341(8) . ?
O003 C00B 1.348(7) . ?
O003 C00D 1.452(6) . ?
N004 C007 1.365(8) . ?
N004 C00B 1.358(7) . ?
N004 C00R 1.465(8) . ?
O005 C009 1.333(9) . ?
O005 C00Z 1.476(14) . ?
O006 C009 1.181(10) . ?
C007 C008 1.420(8) . ?
C007 C00A 1.398(8) . ?
C008 C00C 1.389(9) . ?
C008 C00F 1.427(8) . ?
C009 C00E 1.527(9) . ?
C00A H00A 0.9300 . ?
C00A C00M 1.371(11) . ?
C00B C00F 1.372(8) . ?
C00C H00C 0.9300 . ?
C00C C00L 1.379(10) . ?
C00D H00D 0.9800 . ?
C00D C00I 1.507(8) . ?
C00D C00O 1.538(8) . ?
C00E C00F 1.481(7) . ?
C00E C00O 1.538(8) . ?
C00G C00H 1.466(10) . ?
C00G C00Q 1.405(13) . ?
C00G C00V 1.348(15) . ?
C00H C00K 1.362(9) . ?
C00I C00J 1.391(11) . ?
C00I C00S 1.384(11) . ?
C00J C00T 1.376(14) . ?
C00K C00O 1.521(8) . ?
C00K C00P 1.418(9) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.399(11) . ?
C00M H00M 0.9300 . ?
N00N C00P 1.133(10) . ?
C00O H00O 0.9800 . ?
C00Q H00Q 0.9300 . ?
C00Q C00W 1.363(13) . ?
C00R H00B 0.9600 . ?
C00R H00E 0.9600 . ?
C00R H00F 0.9600 . ?
C00S H00S 0.9300 . ?
C00S C00U 1.382(12) . ?
C00T H00T 0.9300 . ?
C00T C00Y 1.41(3) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.36(2) . ?
C00V H00V 0.9300 . ?
C00V C010 1.446(16) . ?
C00W H00W 0.9300 . ?
C00W C00X 1.38(2) . ?
C00X H00X 0.9300 . ?
C00X C010 1.337(18) . ?
C00Y H00Y 0.9300 . ?
C00Z H00G 0.9600 . ?
C00Z H00H 0.9600 . ?
C00Z H00I 0.9600 . ?
C010 H010 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
C00H O002 C00E 107.9(5) . . ?
C00B O003 C00D 110.0(4) . . ?
C007 N004 C00R 127.2(5) . . ?
C00B N004 C007 107.3(5) . . ?
C00B N004 C00R 125.5(5) . . ?
C009 O005 C00Z 115.4(9) . . ?
N004 C007 C008 109.0(5) . . ?
N004 C007 C00A 129.8(6) . . ?
C00A C007 C008 121.2(6) . . ?
C007 C008 C00F 106.1(5) . . ?
C00C C008 C007 119.6(5) . . ?
C00C C008 C00F 134.3(5) . . ?
O005 C009 C00E 111.2(7) . . ?
O006 C009 O005 125.2(7) . . ?
O006 C009 C00E 123.4(6) . . ?
C007 C00A H00A 121.0 . . ?
C00M C00A C007 118.0(6) . . ?
C00M C00A H00A 121.0 . . ?
O003 C00B N004 120.6(5) . . ?
O003 C00B C00F 127.5(5) . . ?
N004 C00B C00F 111.9(5) . . ?
C008 C00C H00C 120.8 . . ?
C00L C00C C008 118.5(6) . . ?
C00L C00C H00C 120.8 . . ?
O003 C00D H00D 108.9 . . ?
O003 C00D C00I 107.2(4) . . ?
O003 C00D C00O 109.8(4) . . ?
C00I C00D H00D 108.9 . . ?
C00I C00D C00O 112.9(4) . . ?
C00O C00D H00D 108.9 . . ?
O002 C00E C009 109.1(5) . . ?
O002 C00E C00F 111.7(5) . . ?
O002 C00E C00O 104.8(5) . . ?
C009 C00E C00O 110.4(5) . . ?
C00F C00E C009 109.0(5) . . ?
C00F C00E C00O 111.7(4) . . ?
C008 C00F C00E 133.8(5) . . ?
C00B C00F C008 105.7(5) . . ?
C00B C00F C00E 120.0(5) . . ?
C00Q C00G C00H 117.4(8) . . ?
C00V C00G C00H 121.3(8) . . ?
C00V C00G C00Q 121.2(8) . . ?
O002 C00H C00G 115.8(6) . . ?
O002 C00H C00K 112.7(6) . . ?
C00K C00H C00G 131.4(6) . . ?
C00J C00I C00D 121.8(7) . . ?
C00S C00I C00D 119.5(6) . . ?
C00S C00I C00J 118.6(7) . . ?
C00I C00J Br01 121.2(6) . . ?
C00T C00J Br01 117.8(10) . . ?
C00T C00J C00I 121.0(11) . . ?
C00H C00K C00O 108.6(5) . . ?
C00H C00K C00P 125.8(6) . . ?
C00P C00K C00O 125.5(6) . . ?
C00C C00L H00L 119.1 . . ?
C00C C00L C00M 121.7(6) . . ?
C00M C00L H00L 119.1 . . ?
C00A C00M C00L 121.0(6) . . ?
C00A C00M H00M 119.5 . . ?
C00L C00M H00M 119.5 . . ?
C00D C00O C00E 111.9(4) . . ?
C00D C00O H00O 111.1 . . ?
C00E C00O H00O 111.1 . . ?
C00K C00O C00D 111.7(5) . . ?
C00K C00O C00E 99.6(4) . . ?
C00K C00O H00O 111.1 . . ?
N00N C00P C00K 177.4(12) . . ?
C00G C00Q H00Q 119.8 . . ?
C00W C00Q C00G 120.4(12) . . ?
C00W C00Q H00Q 119.8 . . ?
N004 C00R H00B 109.5 . . ?
N004 C00R H00E 109.5 . . ?
N004 C00R H00F 109.5 . . ?
H00B C00R H00E 109.5 . . ?
H00B C00R H00F 109.5 . . ?
H00E C00R H00F 109.5 . . ?
C00I C00S H00S 119.5 . . ?
C00U C00S C00I 121.0(10) . . ?
C00U C00S H00S 119.5 . . ?
C00J C00T H00T 120.6 . . ?
C00J C00T C00Y 118.8(13) . . ?
C00Y C00T H00T 120.6 . . ?
C00S C00U H00U 120.0 . . ?
C00Y C00U C00S 120.0(13) . . ?
C00Y C00U H00U 120.0 . . ?
C00G C00V H00V 121.5 . . ?
C00G C00V C010 116.9(11) . . ?
C010 C00V H00V 121.5 . . ?
C00Q C00W H00W 120.3 . . ?
C00Q C00W C00X 119.3(11) . . ?
C00X C00W H00W 120.3 . . ?
C00W C00X H00X 119.5 . . ?
C010 C00X C00W 120.9(10) . . ?
C010 C00X H00X 119.5 . . ?
C00T C00Y H00Y 119.7 . . ?
C00U C00Y C00T 120.5(9) . . ?
C00U C00Y H00Y 119.7 . . ?
O005 C00Z H00G 109.5 . . ?
O005 C00Z H00H 109.5 . . ?
O005 C00Z H00I 109.5 . . ?
H00G C00Z H00H 109.5 . . ?
H00G C00Z H00I 109.5 . . ?
H00H C00Z H00I 109.5 . . ?
C00V C010 H010 119.4 . . ?
C00X C010 C00V 121.1(13) . . ?
C00X C010 H010 119.4 . . ?

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
Br01 C00J C00T C00Y 177.6(7) . . . . ?
O002 C00E C00F C008 -67.6(8) . . . . ?
O002 C00E C00F C00B 122.0(6) . . . . ?
O002 C00E C00O C00D -94.0(5) . . . . ?
O002 C00E C00O C00K 24.2(6) . . . . ?
O002 C00H C00K C00O 5.6(8) . . . . ?
O002 C00H C00K C00P -176.8(8) . . . . ?
O003 C00B C00F C008 179.2(5) . . . . ?
O003 C00B C00F C00E -8.0(9) . . . . ?
O003 C00D C00I C00J 132.8(6) . . . . ?
O003 C00D C00I C00S -48.2(7) . . . . ?
O003 C00D C00O C00E -59.1(6) . . . . ?
O003 C00D C00O C00K -169.8(4) . . . . ?
N004 C007 C008 C00C 179.1(5) . . . . ?
N004 C007 C008 C00F -0.6(6) . . . . ?
N004 C007 C00A C00M 179.8(6) . . . . ?
N004 C00B C00F C008 -0.9(7) . . . . ?
N004 C00B C00F C00E 171.8(5) . . . . ?
O005 C009 C00E O002 32.0(7) . . . . ?
O005 C009 C00E C00F -90.3(7) . . . . ?
O005 C009 C00E C00O 146.6(6) . . . . ?
O006 C009 C00E O002 -152.4(7) . . . . ?
O006 C009 C00E C00F 85.4(9) . . . . ?
O006 C009 C00E C00O -37.8(9) . . . . ?
C007 N004 C00B O003 -179.6(5) . . . . ?
C007 N004 C00B C00F 0.6(7) . . . . ?
C007 C008 C00C C00L 1.4(9) . . . . ?
C007 C008 C00F C00B 0.9(6) . . . . ?
C007 C008 C00F C00E -170.4(6) . . . . ?
C007 C00A C00M C00L 1.2(11) . . . . ?
C008 C007 C00A C00M -0.9(9) . . . . ?
C008 C00C C00L C00M -1.1(11) . . . . ?
C009 C00E C00F C008 53.0(9) . . . . ?
C009 C00E C00F C00B -117.3(6) . . . . ?
C009 C00E C00O C00D 148.7(5) . . . . ?
C009 C00E C00O C00K -93.1(6) . . . . ?
C00A C007 C008 C00C -0.4(8) . . . . ?
C00A C007 C008 C00F 179.9(5) . . . . ?
C00B O003 C00D C00I 178.9(5) . . . . ?
C00B O003 C00D C00O 55.9(6) . . . . ?
C00B N004 C007 C008 0.1(6) . . . . ?
C00B N004 C007 C00A 179.5(6) . . . . ?
C00C C008 C00F C00B -178.7(7) . . . . ?
C00C C008 C00F C00E 9.9(12) . . . . ?
C00C C00L C00M C00A -0.2(12) . . . . ?
C00D O003 C00B N004 156.1(5) . . . . ?
C00D O003 C00B C00F -24.1(8) . . . . ?
C00D C00I C00J Br01 1.5(8) . . . . ?
C00D C00I C00J C00T -178.6(7) . . . . ?
C00D C00I C00S C00U 179.5(6) . . . . ?
C00E O002 C00H C00G -166.7(6) . . . . ?
C00E O002 C00H C00K 11.3(8) . . . . ?
C00F C008 C00C C00L -179.0(7) . . . . ?
C00F C00E C00O C00D 27.2(7) . . . . ?
C00F C00E C00O C00K 145.3(5) . . . . ?
C00G C00H C00K C00O -176.9(8) . . . . ?
C00G C00H C00K C00P 0.7(14) . . . . ?
C00G C00Q C00W C00X 0.4(15) . . . . ?
C00G C00V C010 C00X 3(2) . . . . ?
C00H O002 C00E C009 95.3(6) . . . . ?
C00H O002 C00E C00F -144.1(5) . . . . ?
C00H O002 C00E C00O -22.9(6) . . . . ?
C00H C00G C00Q C00W -178.5(8) . . . . ?
C00H C00G C00V C010 176.7(10) . . . . ?
C00H C00K C00O C00D 99.7(6) . . . . ?
C00H C00K C00O C00E -18.6(7) . . . . ?
C00I C00D C00O C00E -178.7(5) . . . . ?
C00I C00D C00O C00K 70.7(6) . . . . ?
C00I C00J C00T C00Y -2.3(12) . . . . ?
C00I C00S C00U C00Y 0.4(12) . . . . ?
C00J C00I C00S C00U -1.4(10) . . . . ?
C00J C00T C00Y C00U 1.2(15) . . . . ?
C00O C00D C00I C00J -106.1(6) . . . . ?
C00O C00D C00I C00S 72.9(7) . . . . ?
C00O C00E C00F C008 175.3(6) . . . . ?
C00O C00E C00F C00B 5.0(8) . . . . ?
C00P C00K C00O C00D -77.9(9) . . . . ?
C00P C00K C00O C00E 163.8(8) . . . . ?
C00Q C00G C00H O002 37.6(10) . . . . ?
C00Q C00G C00H C00K -139.9(9) . . . . ?
C00Q C00G C00V C010 -2.6(16) . . . . ?
C00Q C00W C00X C010 0.2(18) . . . . ?
C00R N004 C007 C008 179.1(5) . . . . ?
C00R N004 C007 C00A -1.5(10) . . . . ?
C00R N004 C00B O003 1.4(9) . . . . ?
C00R N004 C00B C00F -178.5(6) . . . . ?
C00S C00I C00J Br01 -177.5(5) . . . . ?
C00S C00I C00J C00T 2.4(10) . . . . ?
C00S C00U C00Y C00T -0.3(15) . . . . ?
C00V C00G C00H O002 -141.8(9) . . . . ?
C00V C00G C00H C00K 40.7(14) . . . . ?
C00V C00G C00Q C00W 0.9(14) . . . . ?
C00W C00X C010 C00V -2(2) . . . . ?
C00Z O005 C009 O006 -4.0(13) . . . . ?
C00Z O005 C009 C00E 171.6(8) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-04-15
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1495971'
_audit_update_record             
;
2016-07-26 deposited with the CCDC.
2016-08-16 downloaded from the CCDC.
;
_audit_creation_date             2016-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.39
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
N N 0.0311 0.0180 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.06732(18)
_cell_length_b                   10.59058(14)
_cell_length_c                   22.9703(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2449.06(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5700
_cell_measurement_temperature    292.6(5)
_cell_measurement_theta_max      72.3190
_cell_measurement_theta_min      5.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.524
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.996
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.606
_diffrn_reflns_theta_min         4.598
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.6(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       ?
_diffrn_orient_matrix_UB_11      -0.0447668000
_diffrn_orient_matrix_UB_12      0.0144130000
_diffrn_orient_matrix_UB_13      -0.0637958000
_diffrn_orient_matrix_UB_21      0.1376635000
_diffrn_orient_matrix_UB_22      -0.0447363000
_diffrn_orient_matrix_UB_23      -0.0207116000
_diffrn_orient_matrix_UB_31      -0.0494311000
_diffrn_orient_matrix_UB_32      -0.1377093000
_diffrn_orient_matrix_UB_33      0.0000188000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.968
_reflns_number_gt                4423
_reflns_number_total             4769
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       ?
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1743 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         4769
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0874P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1225
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00O, C00P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C00R, C00P
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
3. Uiso/Uaniso restraints and constraints
C00O \\sim C00P: within 1.7A with sigma of 0.007 and sigma for terminal atoms
of 0.001
C00R \\sim C00P: within 1.7A with sigma of 0.007 and sigma for terminal atoms
of 0.001
4.a Ternary CH refined with riding coordinates:
 C00B(H00B)
4.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00D(H00D), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00M(H00M), C00O(H00O), C00P(H00P), C00R(H00R)
4.c Idealised Me refined as rotating group:
 C00Q(H00A,H00C,H00E), C00S(H00G,H00J,H00L)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O001 O 0.4938(2) 0.50931(16) 0.67881(7) 0.0711(5) Uani 1 1 d . . . . .
O002 O 0.86097(19) 0.34321(18) 0.52913(9) 0.0751(5) Uani 1 1 d . . . . .
N003 N 0.5699(2) 0.30884(17) 0.69513(8) 0.0568(4) Uani 1 1 d . . . . .
C004 C 0.67308(19) 0.45529(16) 0.56570(8) 0.0445(4) Uani 1 1 d . . . . .
C005 C 0.44361(19) 0.39813(19) 0.55818(9) 0.0506(4) Uani 1 1 d . . . . .
C006 C 0.59573(19) 0.23514(17) 0.60250(8) 0.0451(4) Uani 1 1 d . . . . .
C007 C 0.56217(18) 0.37350(17) 0.59732(8) 0.0437(4) Uani 1 1 d . . . . .
C008 C 0.4777(2) 0.4449(2) 0.50686(9) 0.0560(5) Uani 1 1 d . . . . .
H008 H 0.4169 0.4633 0.4776 0.067 Uiso 1 1 calc R . . . .
C009 C 0.6016(2) 0.20249(18) 0.66076(9) 0.0526(5) Uani 1 1 d . . . . .
C00A C 0.8115(2) 0.3918(2) 0.57083(10) 0.0552(5) Uani 1 1 d . . . . .
C00B C 0.6229(2) 0.46496(18) 0.50082(9) 0.0499(4) Uani 1 1 d . . . . .
H00B H 0.6591 0.3926 0.4795 0.060 Uiso 1 1 calc R . . . .
C00C C 0.6822(2) 0.5829(2) 0.59094(9) 0.0556(5) Uani 1 1 d . . . . .
C00D C 0.6563(3) -0.0073(2) 0.63634(13) 0.0729(7) Uani 1 1 d . . . . .
H00D H 0.6783 -0.0893 0.6472 0.087 Uiso 1 1 calc R . . . .
C00E C 0.5376(2) 0.40990(19) 0.66165(9) 0.0501(4) Uani 1 1 d . . . . .
C00F C 0.6170(2) 0.14369(18) 0.56045(9) 0.0525(4) Uani 1 1 d . . . . .
H00F H 0.6105 0.1634 0.5211 0.063 Uiso 1 1 calc R . . . .
N00G N 0.6986(4) 0.6804(2) 0.60900(13) 0.0918(8) Uani 1 1 d . . . . .
C00H C 0.6483(3) 0.0224(2) 0.57819(12) 0.0655(6) Uani 1 1 d . . . . .
H00H H 0.6640 -0.0398 0.5504 0.079 Uiso 1 1 calc R . . . .
C00I C 0.6324(3) 0.0824(2) 0.67933(11) 0.0692(7) Uani 1 1 d . . . . .
H00I H 0.6369 0.0623 0.7187 0.083 Uiso 1 1 calc R . . . .
C00J C 0.6660(3) 0.5838(2) 0.46905(9) 0.0580(5) Uani 1 1 d . . . . .
C00K C 0.7902(3) 0.5884(3) 0.44250(11) 0.0700(6) Uani 1 1 d . . . . .
H00K H 0.8459 0.5185 0.4445 0.084 Uiso 1 1 calc R . . . .
N00L N 0.2100(2) 0.3300(4) 0.59048(13) 0.0990(9) Uani 1 1 d . . . . .
C00M C 0.8321(4) 0.6956(3) 0.41316(13) 0.0864(9) Uani 1 1 d . . . . .
H00M H 0.9154 0.6970 0.3957 0.104 Uiso 1 1 calc R . . . .
C00N C 0.3132(2) 0.3612(3) 0.57539(10) 0.0627(5) Uani 1 1 d . . . . .
C00O C 0.7523(5) 0.7980(3) 0.40982(15) 0.0977(11) Uani 1 1 d . U . . .
H00O H 0.7800 0.8691 0.3894 0.117 Uiso 1 1 calc R . . . .
C00P C 0.6292(5) 0.7970(3) 0.43685(16) 0.1031(11) Uani 1 1 d . U . . .
H00P H 0.5754 0.8684 0.4355 0.124 Uiso 1 1 calc R . . . .
C00Q C 0.8779(3) 0.3950(3) 0.62858(13) 0.0806(8) Uani 1 1 d . . . . .
H00A H 0.9571 0.3446 0.6273 0.121 Uiso 1 1 calc GR . . . .
H00C H 0.8187 0.3619 0.6576 0.121 Uiso 1 1 calc GR . . . .
H00E H 0.9006 0.4805 0.6382 0.121 Uiso 1 1 calc GR . . . .
C00R C 0.5858(4) 0.6890(3) 0.46621(13) 0.0808(8) Uani 1 1 d . U . . .
H00R H 0.5027 0.6881 0.4838 0.097 Uiso 1 1 calc R . . . .
C00S C 0.5619(4) 0.3061(3) 0.75877(11) 0.0866(9) Uani 1 1 d . . . . .
H00G H 0.4942 0.2475 0.7705 0.130 Uiso 1 1 calc GR . . . .
H00J H 0.5403 0.3888 0.7730 0.130 Uiso 1 1 calc GR . . . .
H00L H 0.6458 0.2800 0.7745 0.130 Uiso 1 1 calc GR . . . .


_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
O001 C00E 1.207(3) . ?
O002 C00A 1.196(3) . ?
N003 C009 1.412(3) . ?
N003 C00E 1.358(3) . ?
N003 C00S 1.464(3) . ?
C004 C007 1.589(3) . ?
C004 C00A 1.552(3) . ?
C004 C00B 1.577(3) . ?
C004 C00C 1.473(3) . ?
C005 C007 1.517(3) . ?
C005 C008 1.324(3) . ?
C005 C00N 1.426(3) . ?
C006 C007 1.508(2) . ?
C006 C009 1.384(3) . ?
C006 C00F 1.385(3) . ?
C007 C00E 1.547(3) . ?
C008 H008 0.9300 . ?
C008 C00B 1.483(3) . ?
C009 C00I 1.376(3) . ?
C00A C00Q 1.485(4) . ?
C00B H00B 0.9800 . ?
C00B C00J 1.518(3) . ?
C00C N00G 1.125(3) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.375(4) . ?
C00D C00I 1.392(4) . ?
C00F H00F 0.9300 . ?
C00F C00H 1.384(3) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J C00K 1.391(4) . ?
C00J C00R 1.377(4) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.386(4) . ?
N00L C00N 1.144(4) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.352(5) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.386(6) . ?
C00P H00P 0.9300 . ?
C00P C00R 1.398(5) . ?
C00Q H00A 0.9600 . ?
C00Q H00C 0.9600 . ?
C00Q H00E 0.9600 . ?
C00R H00R 0.9300 . ?
C00S H00G 0.9600 . ?
C00S H00J 0.9600 . ?
C00S H00L 0.9600 . ?

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
C009 N003 C00S 123.7(2) . . ?
C00E N003 C009 111.49(16) . . ?
C00E N003 C00S 124.62(19) . . ?
C00A C004 C007 111.11(15) . . ?
C00A C004 C00B 112.82(16) . . ?
C00B C004 C007 104.01(15) . . ?
C00C C004 C007 111.33(16) . . ?
C00C C004 C00A 108.16(17) . . ?
C00C C004 C00B 109.41(16) . . ?
C008 C005 C007 112.83(18) . . ?
C008 C005 C00N 126.0(2) . . ?
C00N C005 C007 120.86(19) . . ?
C009 C006 C007 109.19(16) . . ?
C009 C006 C00F 119.56(18) . . ?
C00F C006 C007 131.24(19) . . ?
C005 C007 C004 100.85(15) . . ?
C005 C007 C00E 113.41(16) . . ?
C006 C007 C004 114.10(15) . . ?
C006 C007 C005 112.95(16) . . ?
C006 C007 C00E 101.69(15) . . ?
C00E C007 C004 114.41(15) . . ?
C005 C008 H008 123.4 . . ?
C005 C008 C00B 113.10(19) . . ?
C00B C008 H008 123.4 . . ?
C006 C009 N003 109.38(17) . . ?
C00I C009 N003 127.9(2) . . ?
C00I C009 C006 122.70(19) . . ?
O002 C00A C004 120.0(2) . . ?
O002 C00A C00Q 122.6(2) . . ?
C00Q C00A C004 117.5(2) . . ?
C004 C00B H00B 107.6 . . ?
C008 C00B C004 102.60(16) . . ?
C008 C00B H00B 107.6 . . ?
C008 C00B C00J 116.47(19) . . ?
C00J C00B C004 114.59(16) . . ?
C00J C00B H00B 107.6 . . ?
N00G C00C C004 174.9(3) . . ?
C00H C00D H00D 119.2 . . ?
C00H C00D C00I 121.5(2) . . ?
C00I C00D H00D 119.2 . . ?
O001 C00E N003 126.16(19) . . ?
O001 C00E C007 125.97(19) . . ?
N003 C00E C007 107.84(15) . . ?
C006 C00F H00F 120.7 . . ?
C00H C00F C006 118.6(2) . . ?
C00H C00F H00F 120.7 . . ?
C00D C00H C00F 120.8(2) . . ?
C00D C00H H00H 119.6 . . ?
C00F C00H H00H 119.6 . . ?
C009 C00I C00D 116.7(2) . . ?
C009 C00I H00I 121.6 . . ?
C00D C00I H00I 121.6 . . ?
C00K C00J C00B 119.8(2) . . ?
C00R C00J C00B 121.7(2) . . ?
C00R C00J C00K 118.5(2) . . ?
C00J C00K H00K 119.5 . . ?
C00M C00K C00J 121.0(3) . . ?
C00M C00K H00K 119.5 . . ?
C00K C00M H00M 119.9 . . ?
C00O C00M C00K 120.2(3) . . ?
C00O C00M H00M 119.9 . . ?
N00L C00N C005 178.2(3) . . ?
C00M C00O H00O 120.0 . . ?
C00M C00O C00P 120.0(3) . . ?
C00P C00O H00O 120.0 . . ?
C00O C00P H00P 120.0 . . ?
C00O C00P C00R 120.1(3) . . ?
C00R C00P H00P 120.0 . . ?
C00A C00Q H00A 109.5 . . ?
C00A C00Q H00C 109.5 . . ?
C00A C00Q H00E 109.5 . . ?
H00A C00Q H00C 109.5 . . ?
H00A C00Q H00E 109.5 . . ?
H00C C00Q H00E 109.5 . . ?
C00J C00R C00P 120.1(3) . . ?
C00J C00R H00R 120.0 . . ?
C00P C00R H00R 120.0 . . ?
N003 C00S H00G 109.5 . . ?
N003 C00S H00J 109.5 . . ?
N003 C00S H00L 109.5 . . ?
H00G C00S H00J 109.5 . . ?
H00G C00S H00L 109.5 . . ?
H00J C00S H00L 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
