# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_mujdcb
#TrackingRef '18132_web_deposit_cif_file_0_JamesDowden_1362063190.MUJDCB.cif'


_nottingham_internal_coll_name   mujdcb
_nottingham_internal_coll_number 12058
_nottingham_internal_coll_client MU/JD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '5 and 20'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   ?
_nottingham_internal_process_user WL
_nottingham_internal_process_date 11/2/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date ?
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 26/2/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 26/2/2013
_nottingham_internal_archive_date 26/2/2013

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O3'
_chemical_formula_sum            'C19 H17 N3 O3'
_chemical_formula_weight         335.35

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8865(5)
_cell_length_b                   9.3125(3)
_cell_length_c                   10.9460(5)
_cell_angle_alpha                90.733(3)
_cell_angle_beta                 112.772(5)
_cell_angle_gamma                97.430(4)
_cell_volume                     826.26(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8488
_cell_measurement_theta_min      4.39
_cell_measurement_theta_max      77.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4299
_exptl_crystal_size_mid          0.0827
_exptl_crystal_size_min          0.0561
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_T_max  1.441
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15441
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.391
_diffrn_reflns_theta_max         77.242
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3480
_reflns_number_gt                3210
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_diffrn_orient_matrix_UB_11      0.0796608000
_diffrn_orient_matrix_UB_12      0.1504285000
_diffrn_orient_matrix_UB_13      0.0724824000
_diffrn_orient_matrix_UB_21      0.0676852000
_diffrn_orient_matrix_UB_22      -0.0712854000
_diffrn_orient_matrix_UB_23      0.1330491000
_diffrn_orient_matrix_UB_31      0.1587092000
_diffrn_orient_matrix_UB_32      -0.0159421000
_diffrn_orient_matrix_UB_33      -0.0212988000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
1 omega -98.00 -3.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -43.7877 125.0000 0.0000 95

#__ type_ start__ end____ width___ exp.time_
2 omega -18.00 64.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 43.7877 -38.0000 150.0000 82

#__ type_ start__ end____ width___ exp.time_
3 omega -13.00 14.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 43.7877 -38.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
4 omega 36.00 63.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- 43.7877 -38.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
5 omega -65.00 11.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 30.0000 -30.0000 76

#__ type_ start__ end____ width___ exp.time_
6 omega -131.00 -68.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 -77.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
7 omega -65.00 -35.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 -77.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
8 omega -131.00 -104.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 -111.0000 -30.0000 27

#__ type_ start__ end____ width___ exp.time_
9 omega 38.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -30.0000 60.0000 31

#__ type_ start__ end____ width___ exp.time_
10 omega 54.00 81.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 90.0000 27

#__ type_ start__ end____ width___ exp.time_
11 omega 116.00 147.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 77.0000 -120.0000 31

#__ type_ start__ end____ width___ exp.time_
12 omega 79.00 106.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -95.0000 150.0000 27

#__ type_ start__ end____ width___ exp.time_
13 omega 74.00 118.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -118.0000 75.0000 44

#__ type_ start__ end____ width___ exp.time_
14 omega 79.00 140.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 111.0000 -60.0000 61

#__ type_ start__ end____ width___ exp.time_
15 omega 54.00 141.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -77.0000 -90.0000 87

#__ type_ start__ end____ width___ exp.time_
16 omega 128.00 154.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 30.0000 30.0000 26

#__ type_ start__ end____ width___ exp.time_
17 omega 68.00 113.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
18 omega 38.00 99.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 120.0000 61

#__ type_ start__ end____ width___ exp.time_
19 omega 41.00 66.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -45.0000 -30.0000 25

#__ type_ start__ end____ width___ exp.time_
20 omega 85.00 148.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 -90.0000 63

#__ type_ start__ end____ width___ exp.time_
21 omega 53.00 109.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -95.0000 120.0000 56

#__ type_ start__ end____ width___ exp.time_
22 omega 88.00 113.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 0.0000 25

#__ type_ start__ end____ width___ exp.time_
23 omega 100.00 133.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 111.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
24 omega 90.00 138.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 77.0000 -60.0000 48

#__ type_ start__ end____ width___ exp.time_
25 omega 72.00 109.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -95.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
26 omega 86.00 153.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 30.0000 67

#__ type_ start__ end____ width___ exp.time_
27 omega 93.00 127.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -61.0000 60.0000 34

#__ type_ start__ end____ width___ exp.time_
28 omega 119.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 111.0000 -90.0000 39

#__ type_ start__ end____ width___ exp.time_
29 omega 50.00 77.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -45.0000 120.0000 27

#__ type_ start__ end____ width___ exp.time_
30 omega 51.00 94.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -61.0000 -180.0000 43

#__ type_ start__ end____ width___ exp.time_
31 omega 89.00 153.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 45.0000 0.0000 64

#__ type_ start__ end____ width___ exp.time_
32 omega 66.00 102.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 -60.0000 36

#__ type_ start__ end____ width___ exp.time_
33 omega 67.00 94.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -95.0000 60.0000 27

#__ type_ start__ end____ width___ exp.time_
34 omega 39.00 116.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -111.0000 -30.0000 77

#__ type_ start__ end____ width___ exp.time_
35 omega 33.00 60.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -95.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
36 omega 109.00 140.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 30.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
37 omega 122.00 157.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 30.0000 -60.0000 35

#__ type_ start__ end____ width___ exp.time_
38 omega 85.00 129.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 60.0000 44

#__ type_ start__ end____ width___ exp.time_
39 omega 92.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 45.0000 -120.0000 66

#__ type_ start__ end____ width___ exp.time_
40 omega -115.00 -14.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -43.7877 -77.0000 120.0000 101

#__ type_ start__ end____ width___ exp.time_
41 omega -115.00 -14.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -43.7877 -77.0000 60.0000 101

#__ type_ start__ end____ width___ exp.time_
42 omega -115.00 -14.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -43.7877 -77.0000 -60.0000 101

#__ type_ start__ end____ width___ exp.time_
43 omega -112.00 -19.00 1.0000 5.0000
omega____ theta____ kappa____ phi______ frames
- -43.7877 -57.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
44 omega -131.00 -51.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 -77.0000 -90.0000 80

#__ type_ start__ end____ width___ exp.time_
45 omega -131.00 -30.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- -60.0000 -77.0000 0.0000 101

#__ type_ start__ end____ width___ exp.time_
46 omega 85.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 90.0000 73

#__ type_ start__ end____ width___ exp.time_
47 omega 85.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
48 omega 38.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -30.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
49 omega 38.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -30.0000 150.0000 31

#__ type_ start__ end____ width___ exp.time_
50 omega 81.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 77.0000 120.0000 77

#__ type_ start__ end____ width___ exp.time_
51 omega 41.00 77.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -45.0000 -60.0000 36

#__ type_ start__ end____ width___ exp.time_
52 omega 38.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -30.0000 -180.0000 31

#__ type_ start__ end____ width___ exp.time_
53 omega 85.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 -60.0000 73

#__ type_ start__ end____ width___ exp.time_
54 omega 38.00 69.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 -30.0000 0.0000 31

#__ type_ start__ end____ width___ exp.time_
55 omega 85.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 0.0000 73

#__ type_ start__ end____ width___ exp.time_
56 omega 85.00 158.00 1.0000 20.0000
omega____ theta____ kappa____ phi______ frames
- 111.0000 61.0000 -180.0000 73

;
_diffrn_measurement_method       '\w scans'

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_structure_solution    
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_computing_publication_material  'enCIFer v1.4'

_refine_special_details          
;
?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
w=1/[\s^2^(Fo^2^)+(0.0424P)^2^+0.2940P]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary     iterative
_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         3480
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0883
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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_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
N1 N 0.33110(11) 0.55115(9) 0.29498(9) 0.02090(19) Uani 1 1 d . . . . .
C2 C 0.21544(13) 0.44827(11) 0.18708(10) 0.0213(2) Uani 1 1 d . . . . .
H2 H 0.1296 0.5012 0.1239 0.026 Uiso 1 1 calc R U . . .
C3 C 0.13361(13) 0.34341(11) 0.26065(10) 0.0203(2) Uani 1 1 d . . . . .
C4 C 0.12167(14) 0.44865(11) 0.36557(11) 0.0232(2) Uani 1 1 d . . . . .
H4A H 0.1233 0.3973 0.4446 0.028 Uiso 1 1 calc R U . . .
H4B H 0.0188 0.4924 0.3284 0.028 Uiso 1 1 calc R U . . .
C5 C 0.27467(13) 0.56656(11) 0.40248(11) 0.0207(2) Uani 1 1 d . . . . .
H5 H 0.3620 0.5447 0.4877 0.025 Uiso 1 1 calc R U . . .
C6 C 0.48113(13) 0.60739(11) 0.30310(11) 0.0213(2) Uani 1 1 d . . . . .
H6 H 0.5438 0.6831 0.3690 0.026 Uiso 1 1 calc R U . . .
C7 C 0.54641(14) 0.55856(11) 0.21881(11) 0.0231(2) Uani 1 1 d . . . . .
C8 C 0.45484(15) 0.43320(12) 0.12685(12) 0.0267(2) Uani 1 1 d . . . . .
H8 H 0.5046 0.3889 0.0763 0.032 Uiso 1 1 calc R U . . .
C9 C 0.30211(15) 0.38020(12) 0.11315(11) 0.0268(2) Uani 1 1 d . . . . .
H9 H 0.2464 0.2966 0.0547 0.032 Uiso 1 1 calc R U . . .
C10 C 0.70585(15) 0.62305(12) 0.23087(12) 0.0263(2) Uani 1 1 d . . . . .
N11 N 0.83518(13) 0.67499(12) 0.24030(12) 0.0359(3) Uani 1 1 d . . . . .
C12 C 0.24561(13) 0.22923(11) 0.32533(10) 0.0212(2) Uani 1 1 d . . . . .
O13 O 0.38496(10) 0.25357(9) 0.41165(8) 0.02757(19) Uani 1 1 d . . . . .
N14 N 0.16186(12) 0.09638(10) 0.26944(9) 0.0238(2) Uani 1 1 d . . . . .
H14 H 0.2026 0.0145 0.2892 0.029 Uiso 1 1 calc R U . . .
C15 C 0.00265(14) 0.10577(11) 0.17648(11) 0.0219(2) Uani 1 1 d . . . . .
C16 C -0.11777(15) -0.00556(12) 0.10156(12) 0.0284(3) Uani 1 1 d . . . . .
H16 H -0.0998 -0.1040 0.1092 0.034 Uiso 1 1 calc R U . . .
C17 C -0.26680(15) 0.03229(14) 0.01425(13) 0.0329(3) Uani 1 1 d . . . . .
H17 H -0.3520 -0.0418 -0.0392 0.039 Uiso 1 1 calc R U . . .
C18 C -0.29332(15) 0.17640(14) 0.00378(13) 0.0322(3) Uani 1 1 d . . . . .
H18 H -0.3957 0.1995 -0.0569 0.039 Uiso 1 1 calc R U . . .
C19 C -0.17072(14) 0.28735(13) 0.08168(12) 0.0271(2) Uani 1 1 d . . . . .
H19 H -0.1890 0.3858 0.0752 0.032 Uiso 1 1 calc R U . . .
C20 C -0.02203(13) 0.25110(11) 0.16858(11) 0.0214(2) Uani 1 1 d . . . . .
C21 C 0.23652(13) 0.71899(11) 0.41654(11) 0.0218(2) Uani 1 1 d . . . . .
O22 O 0.24910(10) 0.81506(8) 0.34707(8) 0.02645(18) Uani 1 1 d . . . . .
O23 O 0.19055(12) 0.72899(8) 0.51804(9) 0.0314(2) Uani 1 1 d . . . . .
C24 C 0.1554(2) 0.87068(13) 0.54876(16) 0.0421(4) Uani 1 1 d . . . . .
H24A H 0.0797 0.8581 0.5957 0.050 Uiso 1 1 calc R U . . .
H24B H 0.0999 0.9167 0.4651 0.050 Uiso 1 1 calc R U . . .
C25 C 0.3111(3) 0.96776(17) 0.63399(19) 0.0606(5) Uani 1 1 d . . . . .
H25A H 0.3717 0.9182 0.7127 0.091 Uiso 1 1 calc R U . . .
H25B H 0.2833 1.0578 0.6617 0.091 Uiso 1 1 calc R U . . .
H25C H 0.3799 0.9906 0.5832 0.091 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0244(5) 0.0153(4) 0.0244(4) -0.0020(3) 0.0113(4) 0.0022(3)
C2 0.0241(5) 0.0160(5) 0.0227(5) 0.0009(4) 0.0084(4) 0.0017(4)
C3 0.0226(5) 0.0152(5) 0.0241(5) 0.0014(4) 0.0099(4) 0.0037(4)
C4 0.0274(5) 0.0153(5) 0.0301(6) -0.0009(4) 0.0149(4) 0.0025(4)
C5 0.0258(5) 0.0148(5) 0.0237(5) 0.0015(4) 0.0118(4) 0.0042(4)
C6 0.0238(5) 0.0152(5) 0.0245(5) 0.0017(4) 0.0088(4) 0.0035(4)
C7 0.0246(5) 0.0193(5) 0.0270(5) 0.0025(4) 0.0113(4) 0.0043(4)
C8 0.0347(6) 0.0215(5) 0.0291(6) -0.0007(4) 0.0181(5) 0.0046(4)
C9 0.0352(6) 0.0210(5) 0.0259(5) -0.0037(4) 0.0153(5) -0.0003(4)
C10 0.0287(6) 0.0233(5) 0.0295(6) 0.0030(4) 0.0130(5) 0.0072(4)
N11 0.0289(6) 0.0334(6) 0.0477(6) 0.0057(5) 0.0175(5) 0.0049(4)
C12 0.0256(5) 0.0175(5) 0.0218(5) 0.0009(4) 0.0104(4) 0.0044(4)
O13 0.0272(4) 0.0233(4) 0.0268(4) -0.0008(3) 0.0041(3) 0.0057(3)
N14 0.0276(5) 0.0143(4) 0.0275(5) 0.0013(3) 0.0078(4) 0.0059(3)
C15 0.0251(5) 0.0187(5) 0.0239(5) 0.0014(4) 0.0115(4) 0.0040(4)
C16 0.0313(6) 0.0188(5) 0.0338(6) -0.0018(4) 0.0123(5) 0.0014(4)
C17 0.0273(6) 0.0289(6) 0.0366(6) -0.0057(5) 0.0087(5) -0.0031(5)
C18 0.0236(6) 0.0336(6) 0.0346(6) 0.0008(5) 0.0062(5) 0.0044(5)
C19 0.0265(6) 0.0231(5) 0.0320(6) 0.0037(4) 0.0110(5) 0.0062(4)
C20 0.0237(5) 0.0178(5) 0.0239(5) 0.0014(4) 0.0109(4) 0.0027(4)
C21 0.0244(5) 0.0161(5) 0.0259(5) -0.0009(4) 0.0112(4) 0.0028(4)
O22 0.0340(4) 0.0166(4) 0.0340(4) 0.0050(3) 0.0176(4) 0.0074(3)
O23 0.0503(5) 0.0171(4) 0.0377(5) -0.0011(3) 0.0294(4) 0.0044(3)
C24 0.0678(10) 0.0202(6) 0.0601(9) -0.0022(6) 0.0486(8) 0.0078(6)
C25 0.0938(14) 0.0319(8) 0.0623(10) -0.0182(7) 0.0421(10) -0.0036(8)

_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
N1 C6 1.3365(14) . ?
N1 C5 1.4587(13) . ?
N1 C2 1.4649(13) . ?
C2 C9 1.4985(15) . ?
C2 C3 1.5558(14) . ?
C2 H2 1.0000 . ?
C3 C20 1.5029(15) . ?
C3 C12 1.5394(14) . ?
C3 C4 1.5437(14) . ?
C4 C5 1.5475(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C21 1.5208(14) . ?
C5 H5 1.0000 . ?
C6 C7 1.3662(15) . ?
C6 H6 0.9500 . ?
C7 C10 1.4208(16) . ?
C7 C8 1.4589(15) . ?
C8 C9 1.3325(17) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 N11 1.1527(16) . ?
C12 O13 1.2222(14) . ?
C12 N14 1.3597(14) . ?
N14 C15 1.4016(14) . ?
N14 H14 0.8800 . ?
C15 C16 1.3800(16) . ?
C15 C20 1.3972(15) . ?
C16 C17 1.3932(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3909(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3959(17) . ?
C18 H18 0.9500 . ?
C19 C20 1.3840(16) . ?
C19 H19 0.9500 . ?
C21 O22 1.2036(13) . ?
C21 O23 1.3299(13) . ?
O23 C24 1.4587(14) . ?
C24 C25 1.503(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C6 N1 C5 123.56(9) . . ?
C6 N1 C2 123.78(9) . . ?
C5 N1 C2 111.97(8) . . ?
N1 C2 C9 111.18(9) . . ?
N1 C2 C3 102.55(8) . . ?
C9 C2 C3 116.12(9) . . ?
N1 C2 H2 108.9 . . ?
C9 C2 H2 108.9 . . ?
C3 C2 H2 108.9 . . ?
C20 C3 C12 102.34(8) . . ?
C20 C3 C4 118.05(9) . . ?
C12 C3 C4 111.78(9) . . ?
C20 C3 C2 113.22(9) . . ?
C12 C3 C2 110.00(9) . . ?
C4 C3 C2 101.63(8) . . ?
C3 C4 C5 105.28(8) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
N1 C5 C21 111.57(8) . . ?
N1 C5 C4 104.39(8) . . ?
C21 C5 C4 113.04(9) . . ?
N1 C5 H5 109.2 . . ?
C21 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
N1 C6 C7 121.55(10) . . ?
N1 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C10 119.29(10) . . ?
C6 C7 C8 118.24(10) . . ?
C10 C7 C8 122.26(10) . . ?
C9 C8 C7 120.62(10) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C2 122.06(10) . . ?
C8 C9 H9 119.0 . . ?
C2 C9 H9 119.0 . . ?
N11 C10 C7 179.74(14) . . ?
O13 C12 N14 126.05(10) . . ?
O13 C12 C3 126.12(9) . . ?
N14 C12 C3 107.83(9) . . ?
C12 N14 C15 111.74(9) . . ?
C12 N14 H14 124.1 . . ?
C15 N14 H14 124.1 . . ?
C16 C15 C20 122.36(10) . . ?
C16 C15 N14 128.24(10) . . ?
C20 C15 N14 109.41(9) . . ?
C15 C16 C17 117.29(11) . . ?
C15 C16 H16 121.4 . . ?
C17 C16 H16 121.4 . . ?
C18 C17 C16 121.28(11) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.57(11) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 118.67(11) . . ?
C20 C19 H19 120.7 . . ?
C18 C19 H19 120.7 . . ?
C19 C20 C15 119.82(10) . . ?
C19 C20 C3 131.52(10) . . ?
C15 C20 C3 108.62(9) . . ?
O22 C21 O23 126.03(10) . . ?
O22 C21 C5 124.60(10) . . ?
O23 C21 C5 109.36(9) . . ?
C21 O23 C24 116.50(9) . . ?
O23 C24 C25 111.07(13) . . ?
O23 C24 H24A 109.4 . . ?
C25 C24 H24A 109.4 . . ?
O23 C24 H24B 109.4 . . ?
C25 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

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
C6 N1 C2 C9 17.58(14) . . . . ?
C5 N1 C2 C9 -153.14(9) . . . . ?
C6 N1 C2 C3 142.33(10) . . . . ?
C5 N1 C2 C3 -28.39(10) . . . . ?
N1 C2 C3 C20 164.45(8) . . . . ?
C9 C2 C3 C20 -74.12(12) . . . . ?
N1 C2 C3 C12 -81.75(10) . . . . ?
C9 C2 C3 C12 39.68(12) . . . . ?
N1 C2 C3 C4 36.81(10) . . . . ?
C9 C2 C3 C4 158.24(9) . . . . ?
C20 C3 C4 C5 -157.59(9) . . . . ?
C12 C3 C4 C5 84.14(10) . . . . ?
C2 C3 C4 C5 -33.14(10) . . . . ?
C6 N1 C5 C21 74.30(12) . . . . ?
C2 N1 C5 C21 -114.96(10) . . . . ?
C6 N1 C5 C4 -163.29(9) . . . . ?
C2 N1 C5 C4 7.45(11) . . . . ?
C3 C4 C5 N1 16.96(10) . . . . ?
C3 C4 C5 C21 138.40(9) . . . . ?
C5 N1 C6 C7 161.30(10) . . . . ?
C2 N1 C6 C7 -8.36(16) . . . . ?
N1 C6 C7 C10 179.40(10) . . . . ?
N1 C6 C7 C8 -5.75(16) . . . . ?
C6 C7 C8 C9 8.83(17) . . . . ?
C10 C7 C8 C9 -176.48(11) . . . . ?
C7 C8 C9 C2 1.95(18) . . . . ?
N1 C2 C9 C8 -14.04(15) . . . . ?
C3 C2 C9 C8 -130.76(12) . . . . ?
C20 C3 C12 O13 -177.38(10) . . . . ?
C4 C3 C12 O13 -50.10(14) . . . . ?
C2 C3 C12 O13 62.02(14) . . . . ?
C20 C3 C12 N14 2.56(11) . . . . ?
C4 C3 C12 N14 129.84(9) . . . . ?
C2 C3 C12 N14 -118.04(9) . . . . ?
O13 C12 N14 C15 178.04(11) . . . . ?
C3 C12 N14 C15 -1.90(12) . . . . ?
C12 N14 C15 C16 -179.24(11) . . . . ?
C12 N14 C15 C20 0.36(13) . . . . ?
C20 C15 C16 C17 1.12(18) . . . . ?
N14 C15 C16 C17 -179.32(11) . . . . ?
C15 C16 C17 C18 -0.41(19) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C17 C18 C19 C20 0.53(19) . . . . ?
C18 C19 C20 C15 0.16(17) . . . . ?
C18 C19 C20 C3 177.57(11) . . . . ?
C16 C15 C20 C19 -1.02(17) . . . . ?
N14 C15 C20 C19 179.35(10) . . . . ?
C16 C15 C20 C3 -178.98(10) . . . . ?
N14 C15 C20 C3 1.40(12) . . . . ?
C12 C3 C20 C19 -179.99(12) . . . . ?
C4 C3 C20 C19 56.85(16) . . . . ?
C2 C3 C20 C19 -61.64(15) . . . . ?
C12 C3 C20 C15 -2.36(11) . . . . ?
C4 C3 C20 C15 -125.52(10) . . . . ?
C2 C3 C20 C15 115.99(10) . . . . ?
N1 C5 C21 O22 0.83(15) . . . . ?
C4 C5 C21 O22 -116.47(12) . . . . ?
N1 C5 C21 O23 -178.11(9) . . . . ?
C4 C5 C21 O23 64.59(12) . . . . ?
O22 C21 O23 C24 -1.24(18) . . . . ?
C5 C21 O23 C24 177.68(11) . . . . ?
C21 O23 C24 C25 -83.27(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N14 H14 O22 0.88 2.01 2.8738(12) 166.1 1_545
C6 H6 O13 0.95 2.28 3.0763(13) 140.8 2_666
C5 H5 O13 1.00 2.60 3.1516(14) 115.0 2_666
C4 H4B N11 0.99 2.45 3.4006(16) 159.7 1_455
C16 H16 N11 0.95 2.65 3.4083(16) 136.8 1_445

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.037

_shelxl_version_number           2012-9
_database_code_depnum_ccdc_archive 'CCDC 927102'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_MUJDCC
#TrackingRef '18133_web_deposit_cif_file_1_JamesDowden_1362063190.MUJDCC.cif'


_nottingham_internal_coll_name   MUJDCC
_nottingham_internal_coll_number 12059
_nottingham_internal_coll_client MU/JD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '300.0000 and 75.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   ?
_nottingham_internal_process_user WL
_nottingham_internal_process_date 12/12/2012
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 12/12/2012
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 12/12/2012
_nottingham_internal_validation_user wl
_nottingham_internal_validation_date 7/2/2012
_nottingham_internal_archive_date 8/2/2012

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

_audit_creation_method           'enCIFer editing of SHELXL-97 created file'
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H21 Br N2 O5, C2 H6 O'
_chemical_formula_sum            'C23 H27 Br N2 O6'
_chemical_formula_weight         507.38

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.5537(12)
_cell_length_b                   9.0560(14)
_cell_length_c                   16.2097(17)
_cell_angle_alpha                83.982(11)
_cell_angle_beta                 81.361(11)
_cell_angle_gamma                67.758(14)
_cell_volume                     1147.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1802
_cell_measurement_theta_min      5.28
_cell_measurement_theta_max      76.87

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.0977
_exptl_crystal_size_mid          0.0628
_exptl_crystal_size_min          0.0111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  1.001
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8522
_diffrn_reflns_av_R_equivalents  0.1171
_diffrn_reflns_av_sigmaI/netI    0.1712
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.28
_diffrn_reflns_theta_max         76.87
_reflns_number_total             4490
_reflns_number_gt                2432
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET)
(compiled Dec 3 2012,18:21:49)
;
_computing_structure_solution    
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;

_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
Olex2 1.2
(compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0480P)^2^+0.6587P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4490
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.0804
_refine_ls_wR_factor_ref         0.2241
_refine_ls_wR_factor_gt          0.1716
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 1.12039(12) 0.32906(12) 0.42756(6) 0.0500(3) Uani 1 1 d . . .
O1 O 0.7011(6) 0.3826(6) 0.3513(3) 0.0353(11) Uani 1 1 d . . .
O2 O 0.7247(7) 0.7152(7) 0.0780(4) 0.0499(15) Uani 1 1 d . . .
O3 O 0.5517(6) 0.6991(6) 0.1955(4) 0.0424(13) Uani 1 1 d . . .
O4 O 1.0664(6) 0.1388(6) 0.0930(3) 0.0371(12) Uani 1 1 d . . .
O5 O 0.8492(7) 0.3261(6) 0.0324(3) 0.0374(12) Uani 1 1 d . . .
N1 N 1.1192(7) 0.3760(7) 0.1704(4) 0.0319(13) Uani 1 1 d . . .
N2 N 0.6966(7) 0.6265(7) 0.3829(4) 0.0298(13) Uani 1 1 d . . .
H2 H 0.6256 0.6396 0.4293 0.036 Uiso 1 1 calc R . .
C1 C 0.8738(9) 0.5166(8) 0.2632(4) 0.0300(15) Uani 1 1 d . . .
C2 C 0.8169(9) 0.4956(8) 0.1800(4) 0.0286(15) Uani 1 1 d . . .
H2A H 0.7568 0.4185 0.1915 0.034 Uiso 1 1 calc R . .
C3 C 0.9814(9) 0.4185(8) 0.1197(5) 0.0306(15) Uani 1 1 d . . .
H3 H 0.9929 0.4992 0.0745 0.037 Uiso 1 1 calc R . .
C4 C 1.2626(9) 0.4097(9) 0.1424(5) 0.0367(17) Uani 1 1 d . . .
H4 H 1.2890 0.4294 0.0842 0.044 Uiso 1 1 calc R . .
C5 C 1.3666(10) 0.4154(10) 0.1960(5) 0.0428(19) Uani 1 1 d . . .
H5 H 1.4662 0.4373 0.1758 0.051 Uiso 1 1 calc R . .
C6 C 1.3249(10) 0.3880(10) 0.2837(5) 0.044(2) Uani 1 1 d . . .
H6 H 1.4023 0.3830 0.3212 0.053 Uiso 1 1 calc R . .
C7 C 1.1784(10) 0.3693(9) 0.3136(5) 0.0399(18) Uani 1 1 d . . .
C8 C 1.0517(8) 0.3719(9) 0.2591(4) 0.0306(15) Uani 1 1 d . . .
H8 H 1.0289 0.2709 0.2719 0.037 Uiso 1 1 calc R . .
C9 C 0.7495(8) 0.4984(8) 0.3371(4) 0.0296(15) Uani 1 1 d . . .
C10 C 0.7704(9) 0.7387(8) 0.3467(4) 0.0268(14) Uani 1 1 d . . .
C11 C 0.7403(10) 0.8874(9) 0.3723(5) 0.0371(17) Uani 1 1 d . . .
H11 H 0.6664 0.9268 0.4216 0.045 Uiso 1 1 calc R . .
C12 C 0.8227(10) 0.9795(9) 0.3230(4) 0.0355(16) Uani 1 1 d . . .
H12 H 0.8041 1.0836 0.3385 0.043 Uiso 1 1 calc R . .
C13 C 0.9308(10) 0.9194(8) 0.2519(5) 0.0339(16) Uani 1 1 d . . .
H13 H 0.9861 0.9830 0.2193 0.041 Uiso 1 1 calc R . .
C14 C 0.9606(9) 0.7676(9) 0.2270(4) 0.0335(16) Uani 1 1 d . . .
H14 H 1.0362 0.7272 0.1783 0.040 Uiso 1 1 calc R . .
C15 C 0.8776(8) 0.6765(8) 0.2745(4) 0.0259(14) Uani 1 1 d . . .
C16 C 0.6963(9) 0.6503(9) 0.1428(5) 0.0350(17) Uani 1 1 d . . .
C17 C 0.4212(11) 0.8513(10) 0.1726(6) 0.051(2) Uani 1 1 d . . .
H17A H 0.3078 0.8431 0.1846 0.061 Uiso 1 1 calc R . .
H17B H 0.4415 0.8767 0.1120 0.061 Uiso 1 1 calc R . .
C18 C 0.4249(12) 0.9803(11) 0.2203(6) 0.054(2) Uani 1 1 d . . .
H18A H 0.5336 0.9948 0.2044 0.081 Uiso 1 1 calc R . .
H18B H 0.4123 0.9517 0.2802 0.081 Uiso 1 1 calc R . .
H18C H 0.3314 1.0800 0.2077 0.081 Uiso 1 1 calc R . .
C19 C 0.9762(9) 0.2745(9) 0.0806(4) 0.0312(15) Uani 1 1 d . . .
C20 C 0.8173(10) 0.2021(9) -0.0072(5) 0.0375(17) Uani 1 1 d . . .
H20A H 0.7549 0.2509 -0.0560 0.045 Uiso 1 1 calc R . .
H20B H 0.9273 0.1194 -0.0275 0.045 Uiso 1 1 calc R . .
C21 C 0.7171(10) 0.1268(11) 0.0521(5) 0.045(2) Uani 1 1 d . . .
H21A H 0.7006 0.0433 0.0246 0.068 Uiso 1 1 calc R . .
H21B H 0.6062 0.2077 0.0704 0.068 Uiso 1 1 calc R . .
H21C H 0.7782 0.0793 0.1007 0.068 Uiso 1 1 calc R . .
O6 O 0.4234(7) 0.7501(7) 0.5063(3) 0.0424(13) Uani 1 1 d . . .
H6A H 0.4022 0.6947 0.5481 0.064 Uiso 1 1 calc R . .
C22 C 0.2744(12) 0.8277(12) 0.4661(6) 0.056(2) Uani 1 1 d . . .
H22A H 0.2858 0.9193 0.4302 0.067 Uiso 1 1 calc R . .
H22B H 0.1750 0.8697 0.5088 0.067 Uiso 1 1 calc R . .
C23 C 0.2442(12) 0.7148(12) 0.4134(6) 0.055(2) Uani 1 1 d . . .
H23A H 0.3399 0.6772 0.3693 0.083 Uiso 1 1 calc R . .
H23B H 0.1388 0.7709 0.3880 0.083 Uiso 1 1 calc R . .
H23C H 0.2345 0.6233 0.4487 0.083 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.0526(5) 0.0595(6) 0.0384(5) -0.0015(4) -0.0178(4) -0.0168(4)
O1 0.038(3) 0.035(3) 0.038(3) 0.000(2) -0.005(2) -0.019(2)
O2 0.056(4) 0.045(3) 0.041(3) 0.007(3) -0.013(3) -0.010(3)
O3 0.034(3) 0.033(3) 0.054(3) -0.006(2) -0.009(2) -0.002(2)
O4 0.032(3) 0.033(3) 0.046(3) -0.005(2) -0.009(2) -0.010(2)
O5 0.047(3) 0.029(3) 0.043(3) -0.011(2) -0.017(2) -0.015(2)
N1 0.031(3) 0.030(3) 0.037(3) -0.007(3) -0.001(2) -0.014(3)
N2 0.028(3) 0.030(3) 0.032(3) -0.005(2) 0.001(2) -0.013(2)
C1 0.032(4) 0.024(3) 0.034(4) 0.000(3) -0.003(3) -0.010(3)
C2 0.031(4) 0.019(3) 0.031(3) -0.006(3) -0.005(3) -0.003(3)
C3 0.029(4) 0.025(4) 0.037(4) -0.003(3) -0.005(3) -0.008(3)
C4 0.032(4) 0.032(4) 0.042(4) -0.001(3) -0.001(3) -0.009(3)
C5 0.033(4) 0.047(5) 0.050(5) -0.016(4) -0.003(3) -0.014(4)
C6 0.034(4) 0.045(5) 0.059(5) -0.019(4) -0.020(4) -0.010(3)
C7 0.039(4) 0.036(4) 0.038(4) -0.007(3) -0.012(3) -0.002(3)
C8 0.027(4) 0.032(4) 0.032(4) -0.006(3) -0.004(3) -0.009(3)
C9 0.026(3) 0.028(4) 0.038(4) -0.005(3) -0.004(3) -0.012(3)
C10 0.034(4) 0.021(3) 0.029(3) -0.002(3) -0.005(3) -0.013(3)
C11 0.040(4) 0.036(4) 0.032(4) -0.006(3) -0.006(3) -0.008(3)
C12 0.046(4) 0.027(4) 0.034(4) -0.004(3) -0.007(3) -0.013(3)
C13 0.047(4) 0.019(3) 0.042(4) 0.004(3) -0.012(3) -0.018(3)
C14 0.025(3) 0.042(4) 0.033(4) -0.002(3) -0.007(3) -0.010(3)
C15 0.025(3) 0.022(3) 0.032(3) -0.004(3) -0.001(3) -0.012(3)
C16 0.032(4) 0.035(4) 0.038(4) -0.008(3) -0.012(3) -0.008(3)
C17 0.044(5) 0.039(5) 0.063(5) -0.010(4) -0.022(4) 0.000(4)
C18 0.056(5) 0.044(5) 0.058(5) -0.003(4) -0.021(4) -0.008(4)
C19 0.038(4) 0.030(4) 0.027(3) -0.006(3) -0.003(3) -0.015(3)
C20 0.050(5) 0.034(4) 0.037(4) -0.011(3) -0.010(3) -0.020(3)
C21 0.046(5) 0.055(5) 0.042(4) -0.009(4) -0.006(4) -0.025(4)
O6 0.041(3) 0.047(3) 0.040(3) -0.005(3) -0.005(2) -0.016(3)
C22 0.058(6) 0.053(6) 0.045(5) -0.002(4) -0.003(4) -0.007(4)
C23 0.049(5) 0.063(6) 0.062(6) -0.006(5) -0.016(4) -0.025(4)

_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 C7 1.873(8) . ?
O1 C9 1.255(9) . ?
O2 C16 1.188(9) . ?
O3 C16 1.343(9) . ?
O3 C17 1.461(10) . ?
O4 C19 1.193(9) . ?
O5 C19 1.342(9) . ?
O5 C20 1.478(8) . ?
N1 C4 1.375(9) . ?
N1 C3 1.447(9) . ?
N1 C8 1.469(9) . ?
N2 C9 1.335(9) . ?
N2 C10 1.424(9) . ?
N2 H2 0.8800 . ?
C1 C15 1.492(10) . ?
C1 C9 1.517(10) . ?
C1 C2 1.553(10) . ?
C1 C8 1.586(9) . ?
C2 C16 1.519(10) . ?
C2 C3 1.552(10) . ?
C2 H2A 1.0000 . ?
C3 C19 1.527(10) . ?
C3 H3 1.0000 . ?
C4 C5 1.351(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.432(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.340(12) . ?
C6 H6 0.9500 . ?
C7 C8 1.490(10) . ?
C8 H8 1.0000 . ?
C10 C11 1.369(10) . ?
C10 C15 1.397(9) . ?
C11 C12 1.402(11) . ?
C11 H11 0.9500 . ?
C12 C13 1.381(10) . ?
C12 H12 0.9500 . ?
C13 C14 1.392(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.387(10) . ?
C14 H14 0.9500 . ?
C17 C18 1.479(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C20 C21 1.477(11) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O6 C22 1.420(11) . ?
O6 H6A 0.8400 . ?
C22 C23 1.514(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C16 O3 C17 116.4(7) . . ?
C19 O5 C20 116.5(6) . . ?
C4 N1 C3 121.1(6) . . ?
C4 N1 C8 123.2(6) . . ?
C3 N1 C8 109.4(5) . . ?
C9 N2 C10 110.9(6) . . ?
C9 N2 H2 124.6 . . ?
C10 N2 H2 124.6 . . ?
C15 C1 C9 102.3(5) . . ?
C15 C1 C2 116.6(6) . . ?
C9 C1 C2 110.7(6) . . ?
C15 C1 C8 116.0(6) . . ?
C9 C1 C8 112.7(6) . . ?
C2 C1 C8 99.0(5) . . ?
C16 C2 C3 112.4(6) . . ?
C16 C2 C1 113.2(6) . . ?
C3 C2 C1 106.8(5) . . ?
C16 C2 H2A 108.1 . . ?
C3 C2 H2A 108.1 . . ?
C1 C2 H2A 108.1 . . ?
N1 C3 C19 112.7(6) . . ?
N1 C3 C2 105.2(6) . . ?
C19 C3 C2 110.6(6) . . ?
N1 C3 H3 109.4 . . ?
C19 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
C5 C4 N1 121.2(7) . . ?
C5 C4 H4 119.4 . . ?
N1 C4 H4 119.4 . . ?
C4 C5 C6 119.2(7) . . ?
C4 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C7 C6 C5 121.0(7) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 123.0(7) . . ?
C6 C7 Br1 122.5(6) . . ?
C8 C7 Br1 114.4(6) . . ?
N1 C8 C7 111.0(6) . . ?
N1 C8 C1 103.0(5) . . ?
C7 C8 C1 118.8(6) . . ?
N1 C8 H8 107.8 . . ?
C7 C8 H8 107.8 . . ?
C1 C8 H8 107.8 . . ?
O1 C9 N2 125.6(6) . . ?
O1 C9 C1 124.9(6) . . ?
N2 C9 C1 109.5(6) . . ?
C11 C10 C15 123.1(6) . . ?
C11 C10 N2 128.4(6) . . ?
C15 C10 N2 108.4(6) . . ?
C10 C11 C12 117.5(7) . . ?
C10 C11 H11 121.3 . . ?
C12 C11 H11 121.3 . . ?
C13 C12 C11 120.3(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C12 C13 C14 121.5(7) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C15 C14 C13 118.7(7) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C10 118.9(6) . . ?
C14 C15 C1 132.2(6) . . ?
C10 C15 C1 108.9(6) . . ?
O2 C16 O3 126.2(7) . . ?
O2 C16 C2 125.8(7) . . ?
O3 C16 C2 108.0(6) . . ?
O3 C17 C18 110.2(7) . . ?
O3 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
O3 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O5 126.0(7) . . ?
O4 C19 C3 125.6(7) . . ?
O5 C19 C3 108.4(6) . . ?
C21 C20 O5 111.3(6) . . ?
C21 C20 H20A 109.4 . . ?
O5 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
O5 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 O6 H6A 109.5 . . ?
O6 C22 C23 111.5(8) . . ?
O6 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
O6 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C15 C1 C2 C16 -28.2(9) . . . . ?
C9 C1 C2 C16 88.2(7) . . . . ?
C8 C1 C2 C16 -153.3(6) . . . . ?
C15 C1 C2 C3 96.0(7) . . . . ?
C9 C1 C2 C3 -147.6(6) . . . . ?
C8 C1 C2 C3 -29.1(7) . . . . ?
C4 N1 C3 C19 105.0(8) . . . . ?
C8 N1 C3 C19 -102.2(7) . . . . ?
C4 N1 C3 C2 -134.4(7) . . . . ?
C8 N1 C3 C2 18.4(7) . . . . ?
C16 C2 C3 N1 133.2(6) . . . . ?
C1 C2 C3 N1 8.5(7) . . . . ?
C16 C2 C3 C19 -104.8(7) . . . . ?
C1 C2 C3 C19 130.5(6) . . . . ?
C3 N1 C4 C5 160.1(7) . . . . ?
C8 N1 C4 C5 11.1(11) . . . . ?
N1 C4 C5 C6 -0.9(12) . . . . ?
C4 C5 C6 C7 -5.2(12) . . . . ?
C5 C6 C7 C8 1.3(12) . . . . ?
C5 C6 C7 Br1 178.7(6) . . . . ?
C4 N1 C8 C7 -13.6(9) . . . . ?
C3 N1 C8 C7 -165.8(6) . . . . ?
C4 N1 C8 C1 114.6(7) . . . . ?
C3 N1 C8 C1 -37.5(7) . . . . ?
C6 C7 C8 N1 7.4(11) . . . . ?
Br1 C7 C8 N1 -170.1(5) . . . . ?
C6 C7 C8 C1 -111.7(8) . . . . ?
Br1 C7 C8 C1 70.8(8) . . . . ?
C15 C1 C8 N1 -86.0(7) . . . . ?
C9 C1 C8 N1 156.6(6) . . . . ?
C2 C1 C8 N1 39.6(6) . . . . ?
C15 C1 C8 C7 37.1(9) . . . . ?
C9 C1 C8 C7 -80.2(8) . . . . ?
C2 C1 C8 C7 162.7(7) . . . . ?
C10 N2 C9 O1 -176.9(7) . . . . ?
C10 N2 C9 C1 1.3(8) . . . . ?
C15 C1 C9 O1 177.0(7) . . . . ?
C2 C1 C9 O1 52.0(9) . . . . ?
C8 C1 C9 O1 -57.8(9) . . . . ?
C15 C1 C9 N2 -1.3(7) . . . . ?
C2 C1 C9 N2 -126.2(6) . . . . ?
C8 C1 C9 N2 123.9(6) . . . . ?
C9 N2 C10 C11 175.9(7) . . . . ?
C9 N2 C10 C15 -0.8(8) . . . . ?
C15 C10 C11 C12 -0.2(11) . . . . ?
N2 C10 C11 C12 -176.5(7) . . . . ?
C10 C11 C12 C13 -0.6(11) . . . . ?
C11 C12 C13 C14 0.3(11) . . . . ?
C12 C13 C14 C15 0.7(11) . . . . ?
C13 C14 C15 C10 -1.5(10) . . . . ?
C13 C14 C15 C1 176.3(7) . . . . ?
C11 C10 C15 C14 1.3(10) . . . . ?
N2 C10 C15 C14 178.2(6) . . . . ?
C11 C10 C15 C1 -176.9(7) . . . . ?
N2 C10 C15 C1 -0.1(7) . . . . ?
C9 C1 C15 C14 -177.1(7) . . . . ?
C2 C1 C15 C14 -56.2(10) . . . . ?
C8 C1 C15 C14 59.9(10) . . . . ?
C9 C1 C15 C10 0.8(7) . . . . ?
C2 C1 C15 C10 121.7(7) . . . . ?
C8 C1 C15 C10 -122.2(6) . . . . ?
C17 O3 C16 O2 -3.8(11) . . . . ?
C17 O3 C16 C2 177.3(6) . . . . ?
C3 C2 C16 O2 -5.1(11) . . . . ?
C1 C2 C16 O2 116.0(8) . . . . ?
C3 C2 C16 O3 173.9(6) . . . . ?
C1 C2 C16 O3 -65.0(8) . . . . ?
C16 O3 C17 C18 -100.0(9) . . . . ?
C20 O5 C19 O4 1.3(11) . . . . ?
C20 O5 C19 C3 -176.6(6) . . . . ?
N1 C3 C19 O4 4.4(10) . . . . ?
C2 C3 C19 O4 -113.0(8) . . . . ?
N1 C3 C19 O5 -177.6(6) . . . . ?
C2 C3 C19 O5 65.0(7) . . . . ?
C19 O5 C20 C21 80.1(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6A O1 0.84 1.93 2.749(7) 164.6 2_666
N2 H2 O6 0.88 1.96 2.793(8) 156.5 .

_diffrn_measured_fraction_theta_max 0.923
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.245
_refine_diff_density_min         -0.981
_refine_diff_density_rms         0.118


_database_code_depnum_ccdc_archive 'CCDC 927103'