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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_592
_database_code_depnum_ccdc_archive 'CCDC 1025491'
_audit_update_record             
;
2014-09-22 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_audit_creation_date             2014-09-22
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_chemical_formula_moiety         'C21 H19 Br N2 O2'
_chemical_formula_sum            'C21 H19 Br N2 O2'
_chemical_formula_weight         411.30
_chemical_oxdiff_formula         'C H O N Br'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   9.1410(4)
_cell_length_b                   9.6496(7)
_cell_length_c                   11.1631(8)
_cell_angle_alpha                75.954(6)
_cell_angle_beta                 80.580(5)
_cell_angle_gamma                74.016(5)
_cell_volume                     913.33(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3847
_cell_measurement_temperature    293
_cell_measurement_theta_max      75.3290
_cell_measurement_theta_min      4.1010
_exptl_absorpt_coefficient_mu    3.209
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4955
_exptl_crystal_description       needle
_exptl_crystal_F_000             419.7381
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6973
_diffrn_reflns_theta_full        75.4347
_diffrn_reflns_theta_max         75.43
_diffrn_reflns_theta_min         4.10
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.9308
_diffrn_measured_fraction_theta_max 0.9915
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00    0.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000   90.0000 99

#__ type_ start__ end____ width___ exp.time_
  2 omega  -55.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -48.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214 -178.0000 -180.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega   11.00   52.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000 -120.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214   38.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  -99.00  -66.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -26.3214  -57.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega -152.00  -86.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000 -111.0000  120.0000 66

#__ type_ start__ end____ width___ exp.time_
  8 omega -129.00  -68.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  178.0000   90.0000 61

#__ type_ start__ end____ width___ exp.time_
  9 omega -152.00  -70.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  -38.0000  -30.0000 82

#__ type_ start__ end____ width___ exp.time_
 10 omega  -39.00    8.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   32.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
 11 omega  -56.00    6.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   21.0000 -120.0000 62

#__ type_ start__ end____ width___ exp.time_
 12 omega  -21.00    5.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  104.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  -51.00    5.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000   43.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 14 omega  -56.00  -25.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  -38.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 15 omega  -74.00  -34.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      -72.5000  104.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega   67.00  132.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607   64.0000 -150.0000 65

#__ type_ start__ end____ width___ exp.time_
 17 omega   57.00  150.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  178.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  106.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  -64.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
 19 omega   87.00  147.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  142.0000 -104.0000 60

#__ type_ start__ end____ width___ exp.time_
 20 omega   88.00  114.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -       75.1607  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   86.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   43.00  101.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 23 omega  119.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000 -180.0000 59

#__ type_ start__ end____ width___ exp.time_
 24 omega   68.00   94.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega  135.00  166.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 26 omega  108.00  134.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  104.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   41.00   97.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000    0.0000  -90.0000 56

#__ type_ start__ end____ width___ exp.time_
 28 omega  129.00  155.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000    0.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 29 omega   57.00  113.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 30 omega   44.00  111.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 31 omega   45.00   80.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -32.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 32 omega  112.00  174.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
 33 omega   91.00  177.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
 34 omega   44.00   94.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  -30.0000 50

#__ type_ start__ end____ width___ exp.time_
 35 omega  123.00  165.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  138.0000   30.0000 42

#__ type_ start__ end____ width___ exp.time_
 36 omega   69.00   95.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   50.00   90.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
 38 omega   49.00   74.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega   51.00   93.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -43.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
 40 omega  153.00  178.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 41 omega   80.00  109.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 42 omega   73.00  103.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000  -90.0000 30

#__ type_ start__ end____ width___ exp.time_
 43 omega   97.00  122.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -128.0000   10.0000 25

#__ type_ start__ end____ width___ exp.time_
 44 omega   83.00  110.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 45 omega   52.00   90.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   30.0000 38

#__ type_ start__ end____ width___ exp.time_
 46 omega   48.00   74.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -128.0000   10.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   49.00   98.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -21.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 48 omega   52.00  151.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -65.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
 49 omega   71.00   99.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -54.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
 50 omega   86.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   42.00  112.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000 -120.0000 70

#__ type_ start__ end____ width___ exp.time_
 52 omega   47.00   73.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 53 omega  124.00  149.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   65.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 54 omega  114.00  177.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  120.0000 63

#__ type_ start__ end____ width___ exp.time_
 55 omega   78.00  103.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000 -104.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 56 omega  110.00  135.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000  -89.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
 57 omega   88.00  125.00   1.0000    1.8000
omega____ theta____ kappa____ phi______ frames
    -      124.0000   77.0000  150.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0429915000
_diffrn_orient_matrix_UB_12      -0.0966698000
_diffrn_orient_matrix_UB_13      -0.0979719000
_diffrn_orient_matrix_UB_21      -0.0041369000
_diffrn_orient_matrix_UB_22      0.1387372000
_diffrn_orient_matrix_UB_23      -0.1039850000
_diffrn_orient_matrix_UB_31      0.1708902000
_diffrn_orient_matrix_UB_32      -0.0154456000
_diffrn_orient_matrix_UB_33      0.0068107000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              12
_reflns_limit_k_min              -11
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                3290
_reflns_number_total             3753
_reflns_odcompleteness_completeness 93.08
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.6467
_refine_diff_density_min         -0.5938
_refine_diff_density_rms         0.0729
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             10.7709
_refine_ls_goodness_of_fit_ref   1.0518
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0435
_refine_ls_restrained_S_all      1.0518
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²+0.1735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1277
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C8(H8a,H8b), C7(H7a,H7b), C3(H3a,H3b)
2.c Aromatic/amide H refined with riding coordinates:
 N18(H18), C15(H15), C24(H24), C9(H9), C25(H25), C14(H14), C21(H21), C22(H22),
 C12(H12), C11(H11)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br26 Br -0.23665(3) 0.21237(4) 0.85112(3) 0.06340(15) Uani 1.000000 .
O19 O 1.4135(2) 0.0758(3) 0.2837(2) 0.0631(6) Uani 1.000000 .
O17 O 0.3458(2) 0.4041(3) 0.4054(2) 0.0711(7) Uani 1.000000 .
N1 N 1.1127(2) 0.3092(2) 0.10140(17) 0.0373(4) Uani 1.000000 .
C23 C -0.0432(3) 0.2139(3) 0.7587(2) 0.0406(5) Uani 1.000000 .
N18 N 0.3905(2) 0.2125(2) 0.5705(2) 0.0463(5) Uani 1.000000 .
H18 H 0.4621(2) 0.1427(2) 0.6044(2) 0.0555(6) Uiso 1.000000 R
C15 C 0.8655(3) 0.1799(3) 0.4782(2) 0.0408(5) Uani 1.000000 .
H15 H 0.9349(3) 0.1302(3) 0.5360(2) 0.0490(6) Uiso 1.000000 R
C24 C 0.0728(3) 0.0862(3) 0.7722(2) 0.0443(5) Uani 1.000000 .
H24 H 0.0561(3) 0.0001(3) 0.8251(2) 0.0531(6) Uiso 1.000000 R
C9 C 1.0863(2) 0.1886(3) 0.3228(2) 0.0383(5) Uani 1.000000 .
H9 H 1.1424(2) 0.1337(3) 0.3884(2) 0.0460(6) Uiso 1.000000 R
C10 C 0.9206(2) 0.2282(3) 0.3557(2) 0.0361(4) Uani 1.000000 .
C25 C 0.2142(3) 0.0882(3) 0.7060(2) 0.0425(5) Uani 1.000000 .
H25 H 0.2924(3) 0.0023(3) 0.7134(2) 0.0510(6) Uiso 1.000000 R
C6 C 1.1702(2) 0.2178(2) 0.2148(2) 0.0362(4) Uani 1.000000 .
C20 C 0.2405(2) 0.2170(3) 0.6286(2) 0.0386(5) Uani 1.000000 .
C5 C 1.3404(3) 0.1619(3) 0.2029(2) 0.0423(5) Uani 1.000000 .
C2 C 1.1673(3) 0.2296(3) 0.0000(3) 0.0515(6) Uani 1.000000 .
H2a H 1.1262(3) 0.1433(3) 0.0182(3) 0.0618(7) Uiso 1.000000 R
H2b H 1.1291(3) 0.2925(3) -0.0760(3) 0.0618(7) Uiso 1.000000 R
C8 C 1.1753(3) 0.4395(3) 0.0719(3) 0.0484(6) Uani 1.000000 .
H8a H 1.1412(3) 0.5017(3) -0.0057(3) 0.0581(7) Uiso 1.000000 R
H8b H 1.1367(3) 0.4958(3) 0.1365(3) 0.0581(7) Uiso 1.000000 R
C14 C 0.7109(3) 0.2036(3) 0.5164(2) 0.0438(5) Uani 1.000000 .
H14 H 0.6777(3) 0.1694(3) 0.5989(2) 0.0525(6) Uiso 1.000000 R
C21 C 0.1223(3) 0.3449(3) 0.6148(2) 0.0438(5) Uani 1.000000 .
H21 H 0.1389(3) 0.4315(3) 0.5627(2) 0.0525(6) Uiso 1.000000 R
C16 C 0.4350(3) 0.3060(3) 0.4667(2) 0.0459(6) Uani 1.000000 .
C22 C -0.0205(3) 0.3420(3) 0.6797(2) 0.0451(5) Uani 1.000000 .
H22 H -0.1006(3) 0.4263(3) 0.6699(2) 0.0541(6) Uiso 1.000000 R
C7 C 1.3515(4) 0.3966(4) 0.0606(3) 0.0646(9) Uani 1.000000 .
H7a H 1.3917(4) 0.4434(4) -0.0203(3) 0.0775(10) Uiso 1.000000 R
H7b H 1.3873(4) 0.4297(4) 0.1234(3) 0.0775(10) Uiso 1.000000 R
C13 C 0.6044(3) 0.2784(3) 0.4322(2) 0.0407(5) Uani 1.000000 .
C3 C 1.3425(4) 0.1812(5) -0.0199(3) 0.0712(9) Uani 1.000000 .
H3a H 1.3757(4) 0.0751(5) -0.0113(3) 0.0855(11) Uiso 1.000000 R
H3b H 1.3789(4) 0.2268(5) -0.1027(3) 0.0855(11) Uiso 1.000000 R
C4 C 1.4075(3) 0.2290(3) 0.0779(3) 0.0516(6) Uani 1.000000 .
H4 H 1.5195(3) 0.1978(3) 0.0704(3) 0.0619(8) Uiso 1.000000 R
C12 C 0.6581(3) 0.3303(4) 0.3104(2) 0.0564(8) Uani 1.000000 .
H12 H 0.5883(3) 0.3835(4) 0.2537(2) 0.0677(9) Uiso 1.000000 R
C11 C 0.8127(3) 0.3048(4) 0.2714(2) 0.0541(7) Uani 1.000000 .
H11 H 0.8455(3) 0.3387(4) 0.1887(2) 0.0649(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br26 C23 1.897(2) .
O19 C5 1.216(3) .
O17 C16 1.214(3) .
N1 C6 1.441(3) .
N1 C2 1.465(3) .
N1 C8 1.467(3) .
C23 C24 1.381(4) .
C23 C22 1.379(4) .
N18 C20 1.412(3) .
N18 C16 1.365(3) .
C15 C10 1.391(3) .
C15 C14 1.379(3) .
C24 C25 1.382(3) .
C9 C10 1.464(3) .
C9 C6 1.332(3) .
C10 C11 1.404(3) .
C25 C20 1.387(3) .
C6 C5 1.494(3) .
C20 C21 1.394(3) .
C5 C4 1.497(3) .
C2 C3 1.535(4) .
C8 C7 1.540(4) .
C14 C13 1.391(3) .
C21 C22 1.389(3) .
C16 C13 1.498(3) .
C7 C4 1.530(5) .
C13 C12 1.388(3) .
C3 C4 1.539(5) .
C12 C11 1.381(3) .

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
C2 N1 C6 109.7(2) . .
C8 N1 C6 107.48(18) . .
C8 N1 C2 108.2(2) . .
C24 C23 Br26 119.26(19) . .
C22 C23 Br26 119.63(18) . .
C22 C23 C24 121.1(2) . .
C16 N18 C20 127.5(2) . .
C14 C15 C10 121.9(2) . .
C25 C24 C23 119.1(2) . .
C6 C9 C10 130.91(19) . .
C9 C10 C15 117.62(19) . .
C11 C10 C15 117.5(2) . .
C11 C10 C9 124.7(2) . .
C20 C25 C24 120.7(2) . .
C9 C6 N1 125.57(19) . .
C5 C6 N1 113.04(19) . .
C5 C6 C9 121.32(19) . .
C25 C20 N18 117.3(2) . .
C21 C20 N18 122.9(2) . .
C21 C20 C25 119.8(2) . .
C6 C5 O19 124.8(2) . .
C4 C5 O19 125.1(2) . .
C4 C5 C6 110.15(19) . .
C3 C2 N1 112.6(2) . .
C7 C8 N1 111.6(2) . .
C13 C14 C15 120.4(2) . .
C22 C21 C20 119.4(2) . .
N18 C16 O17 123.4(2) . .
C13 C16 O17 121.7(2) . .
C13 C16 N18 114.9(2) . .
C21 C22 C23 119.8(2) . .
C4 C7 C8 108.9(2) . .
C16 C13 C14 123.2(2) . .
C12 C13 C14 118.2(2) . .
C12 C13 C16 118.5(2) . .
C4 C3 C2 108.2(2) . .
C7 C4 C5 107.9(2) . .
C3 C4 C5 107.4(3) . .
C3 C4 C7 108.0(3) . .
C11 C12 C13 121.6(2) . .
C12 C11 C10 120.4(2) . .

####################################################################### 
# 
# 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_exp_617
_audit_block_doi                 10.5517/cc1494yj
_database_code_depnum_ccdc_archive 'CCDC 1051487'
_audit_update_record             
;
2015-02-27 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;
_audit_creation_date             2015-01-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.06 svn.r3119 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17.5 H15 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z'

_cell_length_a                   5.8724(3)
_cell_length_b                   8.1184(3)
_cell_length_c                   17.0501(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.221(5)
_cell_angle_gamma                90.00
_cell_volume                     810.64(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.9940
_cell_measurement_theta_min      5.2030
_exptl_absorpt_coefficient_mu    0.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53437
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3740
_diffrn_reflns_theta_full        73.10
_diffrn_reflns_theta_max         73.10
_diffrn_reflns_theta_min         5.20
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0851
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   11.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -27.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega -109.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -50.0000   30.0000 76

#__ type_ start__ end____ width___ exp.time_
  4 omega   86.00  118.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -11.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -38.0000   30.0000 93

#__ type_ start__ end____ width___ exp.time_
  6 omega   24.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -99.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   73.00   99.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   47.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  136.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   88.00  114.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
 13 omega   42.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 87

#__ type_ start__ end____ width___ exp.time_
 14 omega  149.00  176.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   85.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -92.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 16 omega  120.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   71.00  104.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega  108.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000 -180.0000 55

#__ type_ start__ end____ width___ exp.time_
 19 omega   44.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 20 omega   67.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   61.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  117.00  147.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -180.0000 30

#__ type_ start__ end____ width___ exp.time_
 23 omega   67.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2465333000
_diffrn_orient_matrix_UB_12      -0.0041504000
_diffrn_orient_matrix_UB_13      0.0251079000
_diffrn_orient_matrix_UB_21      -0.0912914000
_diffrn_orient_matrix_UB_22      0.0193009000
_diffrn_orient_matrix_UB_23      -0.0865775000
_diffrn_orient_matrix_UB_31      -0.0041303000
_diffrn_orient_matrix_UB_32      -0.1887548000
_diffrn_orient_matrix_UB_33      -0.0094066000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2009
_reflns_number_total             2183
_reflns_odcompleteness_completeness 89.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.861
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(7)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.310
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2183
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0850
_refine_ls_restrained_S_all      1.490
_refine_ls_shift/su_max          3.281
_refine_ls_shift/su_mean         0.271
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1573P)²+0.0026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2430
_refine_ls_wR_factor_ref         0.2507
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C18-C1AA \\sim C1AA-C2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C18: within 1.7A with sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C2) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
4. Others
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C18(H18)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B)
5.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C12(H12), C14(H14), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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
O20 O 0.8239(6) 0.1766(6) -0.01174(19) 0.0701(10) Uani 1 1 d . . .
O19 O 0.9855(12) 0.8276(9) 0.4430(3) 0.117(2) Uani 1 1 d . . .
O17 O 1.2286(8) 0.9418(6) 0.3667(2) 0.0816(12) Uani 1 1 d . . .
C9 C 0.8840(7) 0.3734(5) 0.1291(3) 0.0501(9) Uani 1 1 d . . .
H9 H 0.9487 0.4059 0.0834 0.060 Uiso 1 1 calc R . .
C0AA C 0.7612(6) 0.2350(5) 0.1232(2) 0.0483(9) Uani 1 1 d . . .
C10 C 0.9317(7) 0.4809(5) 0.1968(3) 0.0505(9) Uani 1 1 d . . .
C11 C 1.1205(7) 0.5843(6) 0.1960(3) 0.0541(9) Uani 1 1 d . . .
H11 H 1.2111 0.5809 0.1535 0.065 Uiso 1 1 calc R . .
C7 C 0.6942(9) -0.1147(7) 0.1231(4) 0.0722(14) Uani 1 1 d . . .
H7A H 0.5962 -0.2072 0.1332 0.087 Uiso 1 1 calc R . .
H7B H 0.8386 -0.1573 0.1076 0.087 Uiso 1 1 calc R . .
N1 N 0.6458(6) 0.1601(5) 0.1862(2) 0.0572(9) Uani 1 1 d . . .
C12 C 1.1757(7) 0.6924(6) 0.2576(3) 0.0588(10) Uani 1 1 d . . .
H12 H 1.3052 0.7582 0.2566 0.071 Uiso 1 1 calc R . .
C16 C 1.0814(10) 0.8277(7) 0.3838(3) 0.0657(12) Uani 1 1 d . . .
C3 C 0.7333(7) 0.1404(6) 0.0477(3) 0.0527(9) Uani 1 1 d . . .
C13 C 1.0407(8) 0.7034(6) 0.3201(3) 0.0567(10) Uani 1 1 d . . .
C5 C 0.3522(8) 0.0595(8) 0.0831(4) 0.0732(14) Uani 1 1 d . . .
H5A H 0.2833 0.1346 0.0439 0.088 Uiso 1 1 calc R . .
H5B H 0.2472 -0.0311 0.0891 0.088 Uiso 1 1 calc R . .
C8 C 0.7334(9) -0.0115(7) 0.1962(3) 0.0678(13) Uani 1 1 d . . .
H8A H 0.6592 -0.0638 0.2387 0.081 Uiso 1 1 calc R . .
H8B H 0.8959 -0.0076 0.2113 0.081 Uiso 1 1 calc R . .
C6 C 0.3979(7) 0.1491(8) 0.1615(4) 0.0742(15) Uani 1 1 d . . .
H6A H 0.3347 0.2594 0.1570 0.089 Uiso 1 1 calc R . .
H6B H 0.3206 0.0915 0.2018 0.089 Uiso 1 1 calc R . .
C14 C 0.8478(9) 0.6019(7) 0.3215(3) 0.0678(13) Uani 1 1 d . . .
H14 H 0.7544 0.6088 0.3631 0.081 Uiso 1 1 calc R . .
C15 C 0.7961(8) 0.4912(7) 0.2608(3) 0.0642(12) Uani 1 1 d . . .
H15 H 0.6696 0.4227 0.2627 0.077 Uiso 1 1 calc R . .
C4 C 0.5803(8) -0.0066(6) 0.0561(3) 0.0633(11) Uani 1 1 d . . .
H4 H 0.5576 -0.0682 0.0067 0.076 Uiso 1 1 calc R . .
C18 C 1.2685(13) 1.0766(9) 0.4215(3) 0.0865(18) Uani 1 1 d D . .
H18 H 1.1782 1.0713 0.4675 0.104 Uiso 1 1 calc R . .
C1AA C 1.241(3) 1.2350(14) 0.3753(6) 0.200(8) Uani 1 1 d D . .
H1AA H 1.3115 1.2235 0.3265 0.300 Uiso 1 1 calc R . .
H1AB H 1.3137 1.3233 0.4052 0.300 Uiso 1 1 calc R . .
H1AC H 1.0821 1.2591 0.3648 0.300 Uiso 1 1 calc R . .
C2 C 1.486(4) 1.107(2) 0.4379(17) 0.218(14) Uani 0.50 1 d PDU . .
H2A H 1.5517 1.0208 0.4712 0.327 Uiso 0.50 1 calc PR . .
H2B H 1.5039 1.2104 0.4646 0.327 Uiso 0.50 1 calc PR . .
H2C H 1.5627 1.1104 0.3901 0.327 Uiso 0.50 1 calc PR . .


_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
O20 C3 1.215(5) . ?
O19 C16 1.191(7) . ?
O17 C16 1.314(7) . ?
O17 C18 1.447(7) . ?
C9 H9 0.9300 . ?
C9 C0AA 1.335(6) . ?
C9 C10 1.457(6) . ?
C0AA N1 1.446(6) . ?
C0AA C3 1.496(6) . ?
C10 C11 1.391(6) . ?
C10 C15 1.400(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.389(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.506(8) . ?
C7 C4 1.552(8) . ?
N1 C8 1.490(7) . ?
N1 C6 1.488(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C16 C13 1.489(7) . ?
C3 C4 1.507(7) . ?
C13 C14 1.402(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.529(8) . ?
C5 C4 1.544(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9300 . ?
C4 H4 0.9800 . ?
C18 H18 0.9800 . ?
C18 C1AA 1.510(13) . ?
C18 C2 1.31(2) . ?
C1AA H1AA 0.9665 . ?
C1AA H1AB 0.9669 . ?
C1AA H1AC 0.9665 . ?
C2 H2A 0.9686 . ?
C2 H2B 0.9814 . ?
C2 H2C 0.9760 . ?

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 O17 C18 117.9(4) . . ?
C0AA C9 H9 115.2 . . ?
C0AA C9 C10 129.5(4) . . ?
C10 C9 H9 115.3 . . ?
C9 C0AA N1 125.2(4) . . ?
C9 C0AA C3 121.4(4) . . ?
N1 C0AA C3 113.3(4) . . ?
C11 C10 C9 117.4(4) . . ?
C11 C10 C15 118.1(4) . . ?
C15 C10 C9 124.4(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(4) . . ?
C12 C11 H11 119.4 . . ?
H7A C7 H7B 108.3 . . ?
C8 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C8 C7 C4 109.0(4) . . ?
C4 C7 H7A 109.8 . . ?
C4 C7 H7B 109.9 . . ?
C0AA N1 C8 107.5(4) . . ?
C0AA N1 C6 108.5(4) . . ?
C6 N1 C8 107.4(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.7(4) . . ?
C13 C12 H12 119.6 . . ?
O19 C16 O17 123.3(5) . . ?
O19 C16 C13 123.8(5) . . ?
O17 C16 C13 112.9(4) . . ?
O20 C3 C0AA 124.5(4) . . ?
O20 C3 C4 124.9(4) . . ?
C0AA C3 C4 110.7(4) . . ?
C12 C13 C16 122.5(4) . . ?
C12 C13 C14 119.1(4) . . ?
C14 C13 C16 118.2(4) . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
C6 C5 C4 109.0(4) . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.9 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
N1 C8 C7 113.2(4) . . ?
N1 C8 H8A 108.8 . . ?
N1 C8 H8B 109.0 . . ?
H8A C8 H8B 107.7 . . ?
N1 C6 C5 112.4(4) . . ?
N1 C6 H6A 109.1 . . ?
N1 C6 H6B 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(4) . . ?
C15 C14 H14 120.0 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 120.9(4) . . ?
C14 C15 H15 119.5 . . ?
C7 C4 C5 108.3(5) . . ?
C7 C4 H4 111.5 . . ?
C3 C4 C7 106.9(4) . . ?
C3 C4 C5 106.8(4) . . ?
C3 C4 H4 111.5 . . ?
C5 C4 H4 111.6 . . ?
O17 C18 H18 113.2 . . ?
C1AA C18 O17 107.6(5) . . ?
C1AA C18 H18 113.1 . . ?
C1AA C18 C2 91.0(12) . . ?
C2 C18 O17 112.8(11) . . ?
C2 C18 H18 116.9 . . ?
C18 C1AA H1AA 109.9 . . ?
C18 C1AA H1AB 110.5 . . ?
C18 C1AA H1AC 109.9 . . ?
H1AA C1AA H1AB 108.9 . . ?
H1AA C1AA H1AC 108.8 . . ?
H1AB C1AA H1AC 108.7 . . ?
C18 C2 H2A 106.4 . . ?
C18 C2 H2B 115.2 . . ?
C18 C2 H2C 112.0 . . ?
H2A C2 H2B 106.1 . . ?
H2A C2 H2C 109.0 . . ?
H2B C2 H2C 107.9 . . ?

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
O20 C3 C4 C7 120.1(5) . . . . ?
O20 C3 C4 C5 -124.2(5) . . . . ?
O19 C16 C13 C12 -170.7(7) . . . . ?
O19 C16 C13 C14 13.9(9) . . . . ?
O17 C16 C13 C12 11.7(7) . . . . ?
O17 C16 C13 C14 -163.7(5) . . . . ?
C9 C0AA N1 C8 -123.0(4) . . . . ?
C9 C0AA N1 C6 121.2(5) . . . . ?
C9 C0AA C3 O20 2.8(6) . . . . ?
C9 C0AA C3 C4 -177.9(4) . . . . ?
C9 C10 C11 C12 179.0(4) . . . . ?
C9 C10 C15 C14 -177.2(5) . . . . ?
C0AA C9 C10 C11 159.2(4) . . . . ?
C0AA C9 C10 C15 -23.1(7) . . . . ?
C0AA N1 C8 C7 -59.2(5) . . . . ?
C0AA N1 C6 C5 54.5(6) . . . . ?
C0AA C3 C4 C7 -59.2(5) . . . . ?
C0AA C3 C4 C5 56.5(5) . . . . ?
C10 C9 C0AA N1 -0.3(7) . . . . ?
C10 C9 C0AA C3 -179.6(4) . . . . ?
C10 C11 C12 C13 -1.9(7) . . . . ?
C11 C10 C15 C14 0.4(7) . . . . ?
C11 C12 C13 C16 -174.5(4) . . . . ?
C11 C12 C13 C14 0.9(7) . . . . ?
N1 C0AA C3 O20 -176.5(4) . . . . ?
N1 C0AA C3 C4 2.7(5) . . . . ?
C12 C13 C14 C15 0.6(8) . . . . ?
C16 O17 C18 C1AA -128.9(10) . . . . ?
C16 O17 C18 C2 132.3(16) . . . . ?
C16 C13 C14 C15 176.2(5) . . . . ?
C3 C0AA N1 C8 56.4(4) . . . . ?
C3 C0AA N1 C6 -59.5(5) . . . . ?
C13 C14 C15 C10 -1.3(8) . . . . ?
C8 C7 C4 C3 55.5(5) . . . . ?
C8 C7 C4 C5 -59.3(5) . . . . ?
C8 N1 C6 C5 -61.5(6) . . . . ?
C6 N1 C8 C7 57.4(5) . . . . ?
C6 C5 C4 C7 55.0(6) . . . . ?
C6 C5 C4 C3 -59.8(6) . . . . ?
C15 C10 C11 C12 1.2(6) . . . . ?
C4 C7 C8 N1 2.4(6) . . . . ?
C4 C5 C6 N1 4.8(7) . . . . ?
C18 O17 C16 O19 -2.4(10) . . . . ?
C18 O17 C16 C13 175.2(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.267 0.812 0.589 7.3 0.0 ?
2 0.733 0.313 0.411 7.3 0.0 ?

_olex2_submission_special_instructions 'No special instructions were received'
