# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_3ba
_database_code_depnum_ccdc_archive 'CCDC 1408532'
_audit_update_record             
;
2015-06-24 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-07-28
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H23 N3 O'
_chemical_formula_sum            'C19 H23 N3 O'
_chemical_formula_weight         309.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H23 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.1360(13)
_cell_length_b                   9.7606(13)
_cell_length_c                   13.6208(12)
_cell_angle_alpha                70.976(10)
_cell_angle_beta                 78.653(12)
_cell_angle_gamma                71.791(15)
_cell_volume                     847.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2129
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.8480
_cell_measurement_theta_min      3.8000
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0850
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6398
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9988
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -92.00  -48.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega  -24.00   23.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   24.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega   32.00   95.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714 -178.0000  -60.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   70.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   38.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
  6 omega  -51.00   61.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714  -19.0000 -120.0000 112
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0674991000
_diffrn_orient_matrix_UB_12      0.0697748000
_diffrn_orient_matrix_UB_13      -0.0217288000
_diffrn_orient_matrix_UB_21      -0.0794409000
_diffrn_orient_matrix_UB_22      -0.0342282000
_diffrn_orient_matrix_UB_23      0.0175829000
_diffrn_orient_matrix_UB_31      -0.0143408000
_diffrn_orient_matrix_UB_32      0.0180440000
_diffrn_orient_matrix_UB_33      0.0478239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2632
_reflns_number_total             3619
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0596
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0684P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1378
_refine_ls_wR_factor_ref         0.1594
_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. 
;
_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
O1 O -0.15018(18) 0.70000(14) 0.69797(8) 0.0230(3) Uani 1 1 d . . .
N1 N 0.1832(2) 0.63444(16) 0.65104(9) 0.0211(4) Uani 1 1 d . . .
N2 N -0.0627(2) 0.60501(17) 0.79550(10) 0.0211(4) Uani 1 1 d . . .
N3 N -0.0410(2) 0.74707(17) 0.52284(10) 0.0236(4) Uani 1 1 d . . .
C1 C 0.1483(3) 0.6138(2) 0.76466(11) 0.0193(4) Uani 1 1 d . . .
C2 C 0.0099(3) 0.69051(19) 0.62101(12) 0.0196(4) Uani 1 1 d . . .
C4 C -0.2468(3) 0.7899(2) 0.50069(13) 0.0264(4) Uani 1 1 d . . .
H4A H -0.2612 0.8629 0.4325 0.032 Uiso 1 1 calc R . .
H4B H -0.3320 0.8371 0.5521 0.032 Uiso 1 1 calc R . .
C5 C 0.1173(3) 0.7582(2) 0.43679(12) 0.0239(4) Uani 1 1 d . . .
H5A H 0.0739 0.7514 0.3758 0.029 Uiso 1 1 calc R . .
H5B H 0.2327 0.6742 0.4559 0.029 Uiso 1 1 calc R . .
C6 C 0.2897(3) 0.47357(19) 0.82590(12) 0.0203(4) Uani 1 1 d . . .
C7 C 0.1679(3) 0.75395(19) 0.78547(11) 0.0205(4) Uani 1 1 d . . .
C8 C 0.1747(4) 0.9033(2) 0.40977(15) 0.0384(5) Uani 1 1 d . . .
H8A H 0.2841 0.9034 0.3560 0.058 Uiso 1 1 calc R . .
H8B H 0.2127 0.9124 0.4707 0.058 Uiso 1 1 calc R . .
H8C H 0.0638 0.9865 0.3855 0.058 Uiso 1 1 calc R . .
C9 C -0.3124(3) 0.6551(3) 0.50253(17) 0.0423(6) Uani 1 1 d . . .
H9A H -0.2294 0.6088 0.4511 0.063 Uiso 1 1 calc R . .
H9B H -0.4477 0.6876 0.4872 0.063 Uiso 1 1 calc R . .
H9C H -0.3016 0.5837 0.5705 0.063 Uiso 1 1 calc R . .
C10 C -0.0915(3) 0.4576(2) 0.80904(13) 0.0277(4) Uani 1 1 d . . .
H10A H -0.2308 0.4661 0.8152 0.042 Uiso 1 1 calc R . .
H10B H -0.0367 0.3876 0.8711 0.042 Uiso 1 1 calc R . .
H10C H -0.0260 0.4224 0.7497 0.042 Uiso 1 1 calc R . .
C11 C 0.4156(3) 0.3675(2) 0.77817(12) 0.0244(4) Uani 1 1 d . . .
H11 H 0.4170 0.3827 0.7070 0.029 Uiso 1 1 calc R . .
C12 C 0.5389(3) 0.2394(2) 0.83650(14) 0.0302(5) Uani 1 1 d . . .
H12 H 0.6236 0.1691 0.8041 0.036 Uiso 1 1 calc R . .
C13 C 0.5377(3) 0.2146(2) 0.94269(13) 0.0299(5) Uani 1 1 d . . .
H13 H 0.6193 0.1271 0.9816 0.036 Uiso 1 1 calc R . .
C14 C 0.4146(3) 0.3205(2) 0.99050(13) 0.0298(5) Uani 1 1 d . . .
H14 H 0.4142 0.3049 1.0616 0.036 Uiso 1 1 calc R . .
C15 C 0.2920(3) 0.4495(2) 0.93244(13) 0.0280(4) Uani 1 1 d . . .
H15 H 0.2101 0.5209 0.9647 0.034 Uiso 1 1 calc R . .
C16 C 0.3441(3) 0.7954(2) 0.74758(12) 0.0254(4) Uani 1 1 d . . .
H16 H 0.4450 0.7385 0.7110 0.031 Uiso 1 1 calc R . .
C17 C 0.3706(3) 0.9209(2) 0.76387(13) 0.0314(5) Uani 1 1 d . . .
H17 H 0.4887 0.9478 0.7380 0.038 Uiso 1 1 calc R . .
C18 C 0.2219(3) 1.0061(2) 0.81838(14) 0.0331(5) Uani 1 1 d . . .
H18 H 0.2389 1.0910 0.8286 0.040 Uiso 1 1 calc R . .
C19 C 0.0487(3) 0.9643(2) 0.85743(15) 0.0356(5) Uani 1 1 d . . .
H19 H -0.0511 1.0212 0.8945 0.043 Uiso 1 1 calc R . .
C20 C 0.0208(3) 0.8376(2) 0.84213(14) 0.0292(5) Uani 1 1 d . . .
H20 H -0.0961 0.8094 0.8699 0.035 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.4752(17) . ?
O1 C2 1.392(2) . ?
N1 C1 1.4746(18) . ?
N1 C2 1.275(2) . ?
N2 C1 1.503(2) . ?
N2 C10 1.464(2) . ?
N3 C2 1.345(2) . ?
N3 C4 1.460(2) . ?
N3 C5 1.461(2) . ?
C1 C6 1.520(2) . ?
C1 C7 1.536(2) . ?
C4 C9 1.520(3) . ?
C5 C8 1.508(3) . ?
C6 C11 1.389(2) . ?
C6 C15 1.395(2) . ?
C7 C16 1.392(2) . ?
C7 C20 1.386(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.385(2) . ?
C13 C14 1.382(3) . ?
C14 C15 1.382(3) . ?
C16 C17 1.387(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.375(3) . ?
C19 C20 1.398(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
_geom_angle_publ_flag
C2 O1 N2 103.97(12) . . ?
C2 N1 C1 103.96(14) . . ?
O1 N2 C1 100.11(11) . . ?
C10 N2 O1 103.91(12) . . ?
C10 N2 C1 114.71(14) . . ?
C2 N3 C4 121.93(15) . . ?
C2 N3 C5 118.16(15) . . ?
C4 N3 C5 119.84(13) . . ?
N1 C1 N2 105.54(12) . . ?
N1 C1 C6 113.09(14) . . ?
N1 C1 C7 108.37(13) . . ?
N2 C1 C6 110.72(13) . . ?
N2 C1 C7 108.95(14) . . ?
C6 C1 C7 110.00(13) . . ?
N1 C2 O1 117.33(13) . . ?
N1 C2 N3 128.40(16) . . ?
N3 C2 O1 114.25(15) . . ?
N3 C4 C9 111.85(16) . . ?
N3 C5 C8 112.17(15) . . ?
C11 C6 C1 121.32(14) . . ?
C11 C6 C15 119.10(16) . . ?
C15 C6 C1 119.58(16) . . ?
C16 C7 C1 117.94(15) . . ?
C20 C7 C1 122.93(17) . . ?
C20 C7 C16 119.10(17) . . ?
C12 C11 C6 119.92(15) . . ?
C11 C12 C13 120.74(18) . . ?
C14 C13 C12 119.67(18) . . ?
C13 C14 C15 119.89(16) . . ?
C14 C15 C6 120.65(18) . . ?
C17 C16 C7 120.61(18) . . ?
C18 C17 C16 120.2(2) . . ?
C19 C18 C17 119.48(18) . . ?
C18 C19 C20 120.87(19) . . ?
C7 C20 C19 119.71(19) . . ?

####################################################################### 
# 
# 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_5e
_database_code_depnum_ccdc_archive 'CCDC 1408533'
_audit_update_record             
;
2015-06-24 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2015-03-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 N2 O'
_chemical_formula_sum            'C26 H20 N2 O'
_chemical_formula_weight         376.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H20 N2 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2724(4)
_cell_length_b                   10.5468(4)
_cell_length_c                   10.7163(4)
_cell_angle_alpha                68.395(4)
_cell_angle_beta                 71.217(4)
_cell_angle_gamma                69.263(4)
_cell_volume                     984.70(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9249
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      31.6960
_cell_measurement_theta_min      2.5744
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17304
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.580
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   59.00   88.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   -7.00   42.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -150.0000 49

#__ type_ start__ end____ width___ exp.time_
  3 omega   15.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   67.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   95.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   38.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   67.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -99.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega  -48.00   62.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -19.0000  -60.0000 110

#__ type_ start__ end____ width___ exp.time_
  8 omega  -36.00    6.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661  -77.0000 -120.0000 42

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   45.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -      -24.2661   57.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
 10 omega   -4.00   65.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   77.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
 11 omega   -5.00   74.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   77.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
 12 omega  -43.00   42.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598  -57.0000 -120.0000 85

#__ type_ start__ end____ width___ exp.time_
 13 omega    5.00   94.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -       25.3598   57.0000   30.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0278287000
_diffrn_orient_matrix_UB_12      -0.0694468000
_diffrn_orient_matrix_UB_13      0.0403220000
_diffrn_orient_matrix_UB_21      -0.0633737000
_diffrn_orient_matrix_UB_22      -0.0174171000
_diffrn_orient_matrix_UB_23      0.0077427000
_diffrn_orient_matrix_UB_31      0.0306394000
_diffrn_orient_matrix_UB_32      -0.0225729000
_diffrn_orient_matrix_UB_33      -0.0603399000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3935
_reflns_number_total             4524
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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         0.321
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0423P)²+0.3882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23), C24(H24), C25(H25), C26(H26)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75830(8) 1.02708(8) 0.27511(8) 0.01861(18) Uani 1 1 d . . . . .
N1 N 0.94388(10) 0.83661(10) 0.23933(9) 0.01545(19) Uani 1 1 d . . . . .
N2 N 0.75186(9) 0.90931(9) 0.13398(9) 0.01478(19) Uani 1 1 d . . . . .
C1 C 0.81358(11) 0.93004(11) 0.22295(10) 0.0146(2) Uani 1 1 d . . . . .
C2 C 0.67398(11) 0.82236(11) 0.18655(10) 0.0136(2) Uani 1 1 d . . . . .
C3 C 0.64418(11) 0.74636(11) 0.33709(10) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.60825(11) 0.79763(11) 0.09582(11) 0.0141(2) Uani 1 1 d . . . . .
C5 C 1.02061(11) 0.73550(12) 0.16247(11) 0.0152(2) Uani 1 1 d . . . . .
C6 C 1.01000(11) 0.83966(11) 0.33790(11) 0.0154(2) Uani 1 1 d . . . . .
C7 C 1.13588(12) 0.88063(12) 0.29073(12) 0.0182(2) Uani 1 1 d . . . . .
H7 H 1.1763 0.9084 0.1949 0.022 Uiso 1 1 calc R . . . .
C8 C 1.20212(12) 0.88053(13) 0.38519(13) 0.0216(2) Uani 1 1 d . . . . .
H8 H 1.2883 0.9085 0.3536 0.026 Uiso 1 1 calc R . . . .
C9 C 1.14360(13) 0.84002(12) 0.52531(13) 0.0226(2) Uani 1 1 d . . . . .
H9 H 1.1890 0.8410 0.5893 0.027 Uiso 1 1 calc R . . . .
C10 C 1.01839(13) 0.79808(13) 0.57128(12) 0.0226(2) Uani 1 1 d . . . . .
H10 H 0.9786 0.7696 0.6672 0.027 Uiso 1 1 calc R . . . .
C11 C 0.95072(12) 0.79750(12) 0.47797(12) 0.0198(2) Uani 1 1 d . . . . .
H11 H 0.8651 0.7687 0.5096 0.024 Uiso 1 1 calc R . . . .
C12 C 1.05331(12) 0.77900(12) 0.01949(11) 0.0188(2) Uani 1 1 d . . . . .
H12 H 1.0223 0.8760 -0.0289 0.023 Uiso 1 1 calc R . . . .
C13 C 1.13169(13) 0.67992(13) -0.05253(12) 0.0232(2) Uani 1 1 d . . . . .
H13 H 1.1528 0.7093 -0.1503 0.028 Uiso 1 1 calc R . . . .
C14 C 1.17915(13) 0.53841(13) 0.01749(13) 0.0247(3) Uani 1 1 d . . . . .
H14 H 1.2329 0.4710 -0.0320 0.030 Uiso 1 1 calc R . . . .
C15 C 1.14757(13) 0.49591(13) 0.16032(13) 0.0236(3) Uani 1 1 d . . . . .
H15 H 1.1805 0.3991 0.2085 0.028 Uiso 1 1 calc R . . . .
C16 C 1.06818(12) 0.59369(12) 0.23341(12) 0.0191(2) Uani 1 1 d . . . . .
H16 H 1.0465 0.5640 0.3312 0.023 Uiso 1 1 calc R . . . .
C17 C 0.55887(11) 0.82306(12) 0.43036(11) 0.0162(2) Uani 1 1 d . . . . .
H17 H 0.5207 0.9225 0.3978 0.019 Uiso 1 1 calc R . . . .
C18 C 0.52948(12) 0.75478(13) 0.57046(11) 0.0195(2) Uani 1 1 d . . . . .
H18 H 0.4690 0.8069 0.6333 0.023 Uiso 1 1 calc R . . . .
C19 C 0.58877(13) 0.61007(13) 0.61841(12) 0.0231(3) Uani 1 1 d . . . . .
H19 H 0.5704 0.5636 0.7144 0.028 Uiso 1 1 calc R . . . .
C20 C 0.67498(13) 0.53309(13) 0.52642(12) 0.0230(2) Uani 1 1 d . . . . .
H20 H 0.7160 0.4343 0.5596 0.028 Uiso 1 1 calc R . . . .
C21 C 0.70118(12) 0.60073(12) 0.38571(11) 0.0186(2) Uani 1 1 d . . . . .
H21 H 0.7579 0.5476 0.3228 0.022 Uiso 1 1 calc R . . . .
C22 C 0.49964(11) 0.72913(12) 0.15214(11) 0.0168(2) Uani 1 1 d . . . . .
H22 H 0.4704 0.6945 0.2492 0.020 Uiso 1 1 calc R . . . .
C23 C 0.43375(12) 0.71117(12) 0.06700(12) 0.0191(2) Uani 1 1 d . . . . .
H23 H 0.3591 0.6654 0.1060 0.023 Uiso 1 1 calc R . . . .
C24 C 0.47719(12) 0.76008(12) -0.07452(12) 0.0190(2) Uani 1 1 d . . . . .
H24 H 0.4319 0.7485 -0.1327 0.023 Uiso 1 1 calc R . . . .
C25 C 0.58749(12) 0.82638(12) -0.13166(11) 0.0187(2) Uani 1 1 d . . . . .
H25 H 0.6181 0.8587 -0.2288 0.022 Uiso 1 1 calc R . . . .
C26 C 0.65253(12) 0.84527(11) -0.04758(11) 0.0169(2) Uani 1 1 d . . . . .
H26 H 0.7274 0.8907 -0.0871 0.020 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2197(13) . ?
N1 C1 1.3724(14) . ?
N1 C5 1.4389(13) . ?
N1 C6 1.4425(13) . ?
N2 C1 1.4140(13) . ?
N2 C2 1.2834(14) . ?
C2 C3 1.4974(14) . ?
C2 C4 1.4844(14) . ?
C3 C17 1.3967(15) . ?
C3 C21 1.3942(15) . ?
C4 C22 1.3954(15) . ?
C4 C26 1.4014(15) . ?
C5 C12 1.3896(15) . ?
C5 C16 1.3921(16) . ?
C6 C7 1.3886(15) . ?
C6 C11 1.3904(15) . ?
C7 H7 0.9500 . ?
C7 C8 1.3892(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3881(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3881(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3923(16) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C12 C13 1.3907(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.3870(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3882(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3892(16) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C17 C18 1.3891(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3893(17) . ?
C19 H19 0.9500 . ?
C19 C20 1.3904(17) . ?
C20 H20 0.9500 . ?
C20 C21 1.3920(16) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.3936(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.3843(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.3953(16) . ?
C25 H25 0.9500 . ?
C25 C26 1.3827(15) . ?
C26 H26 0.9500 . ?

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
C1 N1 C5 123.86(9) . . ?
C1 N1 C6 118.80(9) . . ?
C5 N1 C6 117.33(8) . . ?
C2 N2 C1 117.77(9) . . ?
O1 C1 N1 123.14(10) . . ?
O1 C1 N2 122.50(10) . . ?
N1 C1 N2 114.28(9) . . ?
N2 C2 C3 122.52(9) . . ?
N2 C2 C4 119.11(9) . . ?
C4 C2 C3 118.36(9) . . ?
C17 C3 C2 119.35(9) . . ?
C21 C3 C2 121.14(9) . . ?
C21 C3 C17 119.51(10) . . ?
C22 C4 C2 120.44(9) . . ?
C22 C4 C26 119.13(10) . . ?
C26 C4 C2 120.42(9) . . ?
C12 C5 N1 120.78(10) . . ?
C12 C5 C16 120.16(10) . . ?
C16 C5 N1 118.98(9) . . ?
C7 C6 N1 118.90(10) . . ?
C7 C6 C11 120.83(10) . . ?
C11 C6 N1 120.23(10) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.27(10) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.61(11) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.59(10) . . ?
C10 C9 H9 120.2 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.52(11) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 119.18(11) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C5 C12 H12 120.1 . . ?
C5 C12 C13 119.74(11) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.40(11) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.57(11) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.55(11) . . ?
C16 C15 H15 119.7 . . ?
C5 C16 H16 120.2 . . ?
C15 C16 C5 119.56(10) . . ?
C15 C16 H16 120.2 . . ?
C3 C17 H17 119.8 . . ?
C18 C17 C3 120.37(10) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.80(10) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.21(11) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.03(11) . . ?
C21 C20 H20 120.0 . . ?
C3 C21 H21 120.0 . . ?
C20 C21 C3 120.05(10) . . ?
C20 C21 H21 120.0 . . ?
C4 C22 H22 119.8 . . ?
C23 C22 C4 120.47(10) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 119.92(10) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.0 . . ?
C23 C24 C25 119.95(10) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.32(10) . . ?
C26 C25 H25 119.8 . . ?
C4 C26 H26 119.9 . . ?
C25 C26 C4 120.19(10) . . ?
C25 C26 H26 119.9 . . ?

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
N1 C5 C12 C13 177.86(10) . . . . ?
N1 C5 C16 C15 -177.30(10) . . . . ?
N1 C6 C7 C8 -178.44(10) . . . . ?
N1 C6 C11 C10 178.44(10) . . . . ?
N2 C2 C3 C17 68.60(14) . . . . ?
N2 C2 C3 C21 -110.81(12) . . . . ?
N2 C2 C4 C22 -166.04(10) . . . . ?
N2 C2 C4 C26 12.70(15) . . . . ?
C1 N1 C5 C12 55.49(15) . . . . ?
C1 N1 C5 C16 -127.72(11) . . . . ?
C1 N1 C6 C7 -113.92(11) . . . . ?
C1 N1 C6 C11 68.25(14) . . . . ?
C1 N2 C2 C3 1.52(15) . . . . ?
C1 N2 C2 C4 -179.68(9) . . . . ?
C2 N2 C1 O1 -95.23(13) . . . . ?
C2 N2 C1 N1 88.08(12) . . . . ?
C2 C3 C17 C18 179.84(10) . . . . ?
C2 C3 C21 C20 178.31(10) . . . . ?
C2 C4 C22 C23 177.29(10) . . . . ?
C2 C4 C26 C25 -177.72(10) . . . . ?
C3 C2 C4 C22 12.81(15) . . . . ?
C3 C2 C4 C26 -168.45(9) . . . . ?
C3 C17 C18 C19 1.93(16) . . . . ?
C4 C2 C3 C17 -110.21(11) . . . . ?
C4 C2 C3 C21 70.38(13) . . . . ?
C4 C22 C23 C24 0.74(17) . . . . ?
C5 N1 C1 O1 -170.12(10) . . . . ?
C5 N1 C1 N2 6.55(14) . . . . ?
C5 N1 C6 C7 65.40(13) . . . . ?
C5 N1 C6 C11 -112.43(11) . . . . ?
C5 C12 C13 C14 -0.97(17) . . . . ?
C6 N1 C1 O1 9.16(15) . . . . ?
C6 N1 C1 N2 -174.18(9) . . . . ?
C6 N1 C5 C12 -123.79(11) . . . . ?
C6 N1 C5 C16 53.00(13) . . . . ?
C6 C7 C8 C9 0.01(17) . . . . ?
C7 C6 C11 C10 0.66(17) . . . . ?
C7 C8 C9 C10 0.56(18) . . . . ?
C8 C9 C10 C11 -0.53(18) . . . . ?
C9 C10 C11 C6 -0.08(18) . . . . ?
C11 C6 C7 C8 -0.62(17) . . . . ?
C12 C5 C16 C15 -0.49(16) . . . . ?
C12 C13 C14 C15 0.20(18) . . . . ?
C13 C14 C15 C16 0.43(18) . . . . ?
C14 C15 C16 C5 -0.28(18) . . . . ?
C16 C5 C12 C13 1.11(16) . . . . ?
C17 C3 C21 C20 -1.09(16) . . . . ?
C17 C18 C19 C20 -1.29(17) . . . . ?
C18 C19 C20 C21 -0.54(18) . . . . ?
C19 C20 C21 C3 1.73(18) . . . . ?
C21 C3 C17 C18 -0.74(16) . . . . ?
C22 C4 C26 C25 1.03(16) . . . . ?
C22 C23 C24 C25 0.44(17) . . . . ?
C23 C24 C25 C26 -0.87(17) . . . . ?
C24 C25 C26 C4 0.13(17) . . . . ?
C26 C4 C22 C23 -1.46(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_sas169
_database_code_depnum_ccdc_archive 'CCDC 1409104'
_audit_update_record             
;
2015-06-26 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-06-27
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C32 H24 Br N3 O'
_chemical_formula_sum            'C32 H24 Br N3 O'
_chemical_formula_weight         546.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H24 br1 n3 o1'
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'

_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                   8.8129(4)
_cell_length_b                   9.0613(5)
_cell_length_c                   16.1691(7)
_cell_angle_alpha                92.583(4)
_cell_angle_beta                 92.986(4)
_cell_angle_gamma                104.621(4)
_cell_volume                     1245.42(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4977
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0140
_cell_measurement_theta_min      5.0560
_exptl_absorpt_coefficient_mu    2.492
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tables
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11464
_diffrn_reflns_theta_full        72.50
_diffrn_reflns_theta_max         72.50
_diffrn_reflns_theta_min         5.05
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.9689
_diffrn_measured_fraction_theta_max 0.9689
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -104.00  -33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000   30.0000 71

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  150.0000 111

#__ type_ start__ end____ width___ exp.time_
  3 omega    7.00   36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega -112.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -60.0000 101

#__ type_ start__ end____ width___ exp.time_
  5 omega    4.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  -99.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  6 omega   64.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   87.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
  8 omega   77.00  103.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -113.6517 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 10 omega  133.00  159.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   86.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 13 omega  151.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   55.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 35

#__ type_ start__ end____ width___ exp.time_
 15 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   87.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega  116.00  149.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   87.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  140.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
 20 omega   65.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000 -180.0000 81

#__ type_ start__ end____ width___ exp.time_
 21 omega  105.00  130.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   84.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 85

#__ type_ start__ end____ width___ exp.time_
 24 omega  116.00  142.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   35.00   83.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -30.0000 48

#__ type_ start__ end____ width___ exp.time_
 26 omega   39.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -90.0000 59

#__ type_ start__ end____ width___ exp.time_
 27 omega   29.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 28 omega  118.00  143.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   35.00   68.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
 30 omega   73.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 31 omega   37.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
 32 omega   67.00   95.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -59.0000  -56.0000 28

#__ type_ start__ end____ width___ exp.time_
 33 omega  131.00  156.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -113.6517 25

#__ type_ start__ end____ width___ exp.time_
 34 omega   60.00   99.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
 35 omega   50.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -64.0000   61.9156 94

#__ type_ start__ end____ width___ exp.time_
 36 omega   88.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 23
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1073576000
_diffrn_orient_matrix_UB_12      -0.0417653000
_diffrn_orient_matrix_UB_13      -0.0644804000
_diffrn_orient_matrix_UB_21      0.0630790000
_diffrn_orient_matrix_UB_22      0.1704037000
_diffrn_orient_matrix_UB_23      -0.0156126000
_diffrn_orient_matrix_UB_31      0.1314315000
_diffrn_orient_matrix_UB_32      0.0142573000
_diffrn_orient_matrix_UB_33      0.0688067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4211
_reflns_number_total             4826
_reflns_odcompleteness_completeness 92.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.929
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0466P)²+0.5339P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0895
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.12607(3) 0.61622(3) 0.631925(14) 0.02792(9) Uani 1 1 d . . .
O1 O -0.01527(18) 0.22742(18) 0.14923(9) 0.0237(3) Uani 1 1 d . . .
N1 N 0.1573(2) 0.3707(2) 0.25102(11) 0.0211(4) Uani 1 1 d . . .
N3 N 0.1270(2) 0.1062(2) 0.23252(11) 0.0219(4) Uani 1 1 d . . .
N2 N 0.3633(2) 0.5808(2) 0.28680(11) 0.0225(4) Uani 1 1 d . . .
C16 C 0.2062(3) 0.6101(3) 0.52538(13) 0.0228(4) Uani 1 1 d . . .
C21 C 0.6538(3) 0.9754(3) 0.19497(17) 0.0330(5) Uani 1 1 d . . .
H21 H 0.7191 1.0614 0.1746 0.040 Uiso 1 1 calc R . .
C30 C -0.0166(3) -0.3123(3) 0.18179(16) 0.0287(5) Uani 1 1 d . . .
H30 H -0.0524 -0.4012 0.2092 0.034 Uiso 1 1 calc R . .
C1 C 0.2926(3) 0.4521(2) 0.23518(13) 0.0207(4) Uani 1 1 d . . .
C19 C 0.4180(3) 0.7690(3) 0.18079(14) 0.0250(4) Uani 1 1 d . . .
H19 H 0.3245 0.7192 0.1511 0.030 Uiso 1 1 calc R . .
C26 C 0.3796(3) 0.1174(3) 0.46246(14) 0.0257(5) Uani 1 1 d . . .
H26 H 0.4355 0.1202 0.5131 0.031 Uiso 1 1 calc R . .
C24 C 0.1379(3) 0.1131(2) 0.38457(14) 0.0231(4) Uani 1 1 d . . .
H24 H 0.0322 0.1129 0.3831 0.028 Uiso 1 1 calc R . .
C8 C 0.3897(3) 0.4139(2) 0.16835(14) 0.0219(4) Uani 1 1 d . . .
C17 C 0.2748(3) 0.4939(3) 0.50333(14) 0.0238(4) Uani 1 1 d . . .
H17 H 0.2856 0.4221 0.5410 0.029 Uiso 1 1 calc R . .
C12 C 0.4139(3) 0.3213(3) 0.02858(15) 0.0304(5) Uani 1 1 d . . .
H12 H 0.3715 0.2931 -0.0254 0.036 Uiso 1 1 calc R . .
C9 C 0.5438(3) 0.4095(3) 0.18945(15) 0.0253(4) Uani 1 1 d . . .
H9 H 0.5877 0.4407 0.2429 0.030 Uiso 1 1 calc R . .
C7 C 0.3100(2) 0.5932(3) 0.36859(13) 0.0214(4) Uani 1 1 d . . .
C10 C 0.6323(3) 0.3586(3) 0.13096(16) 0.0292(5) Uani 1 1 d . . .
H10 H 0.7346 0.3542 0.1454 0.035 Uiso 1 1 calc R . .
C23 C 0.5985(3) 0.7919(3) 0.30034(16) 0.0278(5) Uani 1 1 d . . .
H23 H 0.6267 0.7566 0.3505 0.033 Uiso 1 1 calc R . .
C11 C 0.5667(3) 0.3144(3) 0.05078(16) 0.0310(5) Uani 1 1 d . . .
H11 H 0.6254 0.2799 0.0116 0.037 Uiso 1 1 calc R . .
C13 C 0.3252(3) 0.3705(3) 0.08747(14) 0.0255(5) Uani 1 1 d . . .
H13 H 0.2228 0.3745 0.0730 0.031 Uiso 1 1 calc R . .
C6 C 0.4604(3) 0.7141(3) 0.25495(14) 0.0223(4) Uani 1 1 d . . .
C18 C 0.3272(3) 0.4860(3) 0.42424(14) 0.0238(4) Uani 1 1 d . . .
H18 H 0.3739 0.4087 0.4086 0.029 Uiso 1 1 calc R . .
C27 C 0.4540(3) 0.1157(2) 0.38895(15) 0.0245(4) Uani 1 1 d . . .
H27 H 0.5600 0.1170 0.3905 0.029 Uiso 1 1 calc R . .
C2 C 0.0855(2) 0.2338(3) 0.20534(13) 0.0212(4) Uani 1 1 d . . .
C25 C 0.2216(3) 0.1149(3) 0.45994(14) 0.0255(5) Uani 1 1 d . . .
H25 H 0.1712 0.1144 0.5091 0.031 Uiso 1 1 calc R . .
C20 C 0.5153(3) 0.8985(3) 0.15088(15) 0.0301(5) Uani 1 1 d . . .
H20 H 0.4872 0.9338 0.1007 0.036 Uiso 1 1 calc R . .
C15 C 0.1913(3) 0.7196(3) 0.47113(14) 0.0248(4) Uani 1 1 d . . .
H15 H 0.1459 0.7977 0.4872 0.030 Uiso 1 1 calc R . .
C22 C 0.6935(3) 0.9219(3) 0.27034(18) 0.0335(6) Uani 1 1 d . . .
H22 H 0.7851 0.9741 0.3010 0.040 Uiso 1 1 calc R . .
C29 C 0.0229(3) -0.1711(3) 0.22613(14) 0.0247(4) Uani 1 1 d . . .
H29 H 0.0113 -0.1657 0.2829 0.030 Uiso 1 1 calc R . .
C14 C 0.2451(3) 0.7117(3) 0.39219(14) 0.0228(4) Uani 1 1 d . . .
H14 H 0.2375 0.7857 0.3553 0.027 Uiso 1 1 calc R . .
C31 C -0.0027(3) -0.3205(3) 0.09691(16) 0.0307(5) Uani 1 1 d . . .
H31 H -0.0310 -0.4146 0.0672 0.037 Uiso 1 1 calc R . .
C33 C 0.0959(3) -0.0467(3) 0.10059(14) 0.0260(5) Uani 1 1 d . . .
H33 H 0.1351 0.0418 0.0733 0.031 Uiso 1 1 calc R . .
C32 C 0.0534(3) -0.1879(3) 0.05636(15) 0.0289(5) Uani 1 1 d . . .
H32 H 0.0627 -0.1934 -0.0007 0.035 Uiso 1 1 calc R . .
C5 C 0.0796(3) -0.0382(3) 0.18557(14) 0.0223(4) Uani 1 1 d . . .
C28 C 0.3714(3) 0.1121(2) 0.31310(14) 0.0229(4) Uani 1 1 d . . .
H28 H 0.4214 0.1100 0.2640 0.027 Uiso 1 1 calc R . .
C4 C 0.2141(3) 0.1116(2) 0.31105(13) 0.0214(4) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C16 1.899(2) . ?
O1 C2 1.225(3) . ?
N1 C1 1.280(3) . ?
N1 C2 1.399(3) . ?
N3 C2 1.381(3) . ?
N3 C5 1.436(3) . ?
N3 C4 1.441(3) . ?
N2 C1 1.391(3) . ?
N2 C7 1.435(3) . ?
N2 C6 1.427(3) . ?
C16 C17 1.382(3) . ?
C16 C15 1.380(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(4) . ?
C21 C22 1.392(4) . ?
C30 H30 0.9300 . ?
C30 C29 1.392(3) . ?
C30 C31 1.385(4) . ?
C1 C8 1.494(3) . ?
C19 H19 0.9300 . ?
C19 C6 1.388(3) . ?
C19 C20 1.390(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.388(3) . ?
C26 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.389(3) . ?
C24 C4 1.396(3) . ?
C8 C9 1.394(3) . ?
C8 C13 1.397(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.387(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.392(4) . ?
C12 C13 1.390(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C7 C18 1.383(3) . ?
C7 C14 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(4) . ?
C23 H23 0.9300 . ?
C23 C6 1.394(3) . ?
C23 C22 1.386(4) . ?
C11 H11 0.9300 . ?
C13 H13 0.9300 . ?
C18 H18 0.9300 . ?
C27 H27 0.9300 . ?
C27 C28 1.388(3) . ?
C25 H25 0.9300 . ?
C20 H20 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.389(3) . ?
C22 H22 0.9300 . ?
C29 H29 0.9300 . ?
C29 C5 1.390(3) . ?
C14 H14 0.9300 . ?
C31 H31 0.9300 . ?
C31 C32 1.386(4) . ?
C33 H33 0.9300 . ?
C33 C32 1.391(3) . ?
C33 C5 1.390(3) . ?
C32 H32 0.9300 . ?
C28 H28 0.9300 . ?
C28 C4 1.384(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
_geom_angle_publ_flag
C1 N1 C2 121.74(18) . . ?
C2 N3 C5 121.47(18) . . ?
C2 N3 C4 120.99(18) . . ?
C5 N3 C4 117.49(18) . . ?
C1 N2 C7 118.96(18) . . ?
C1 N2 C6 121.29(18) . . ?
C6 N2 C7 118.22(17) . . ?
C17 C16 Br1 119.19(17) . . ?
C15 C16 Br1 119.24(17) . . ?
C15 C16 C17 121.5(2) . . ?
C20 C21 H21 120.5 . . ?
C20 C21 C22 119.0(2) . . ?
C22 C21 H21 120.5 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 H30 119.9 . . ?
C31 C30 C29 120.1(2) . . ?
N1 C1 N2 119.06(19) . . ?
N1 C1 C8 125.01(19) . . ?
N2 C1 C8 115.75(19) . . ?
C6 C19 H19 120.0 . . ?
C6 C19 C20 120.0(2) . . ?
C20 C19 H19 120.0 . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C25 C26 C27 119.7(2) . . ?
C25 C24 H24 120.3 . . ?
C25 C24 C4 119.3(2) . . ?
C4 C24 H24 120.3 . . ?
C9 C8 C1 118.7(2) . . ?
C9 C8 C13 119.8(2) . . ?
C13 C8 C1 121.4(2) . . ?
C16 C17 H17 120.5 . . ?
C16 C17 C18 119.1(2) . . ?
C18 C17 H17 120.5 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.7(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C18 C7 N2 118.8(2) . . ?
C18 C7 C14 120.4(2) . . ?
C14 C7 N2 120.9(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C6 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C22 C23 C6 119.7(2) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C19 C6 N2 121.2(2) . . ?
C19 C6 C23 119.7(2) . . ?
C23 C6 N2 119.1(2) . . ?
C17 C18 H18 120.0 . . ?
C7 C18 C17 120.0(2) . . ?
C7 C18 H18 120.0 . . ?
C26 C27 H27 119.8 . . ?
C28 C27 C26 120.5(2) . . ?
C28 C27 H27 119.8 . . ?
O1 C2 N1 121.6(2) . . ?
O1 C2 N3 122.9(2) . . ?
N3 C2 N1 115.22(19) . . ?
C26 C25 C24 120.5(2) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C16 C15 H15 120.4 . . ?
C16 C15 C14 119.1(2) . . ?
C14 C15 H15 120.4 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.9(2) . . ?
C23 C22 H22 119.6 . . ?
C30 C29 H29 120.0 . . ?
C5 C29 C30 120.1(2) . . ?
C5 C29 H29 120.0 . . ?
C7 C14 C15 119.8(2) . . ?
C7 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.8(2) . . ?
C32 C31 H31 120.1 . . ?
C32 C33 H33 120.1 . . ?
C5 C33 H33 120.1 . . ?
C5 C33 C32 119.9(2) . . ?
C31 C32 C33 120.3(2) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C29 C5 N3 119.6(2) . . ?
C33 C5 N3 120.6(2) . . ?
C33 C5 C29 119.8(2) . . ?
C27 C28 H28 120.2 . . ?
C4 C28 C27 119.6(2) . . ?
C4 C28 H28 120.2 . . ?
C24 C4 N3 119.6(2) . . ?
C28 C4 N3 119.9(2) . . ?
C28 C4 C24 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C16 C17 C18 177.30(16) . . . . ?
Br1 C16 C15 C14 -177.76(17) . . . . ?
N1 C1 C8 C9 -126.2(2) . . . . ?
N1 C1 C8 C13 48.4(3) . . . . ?
N2 C1 C8 C9 48.9(3) . . . . ?
N2 C1 C8 C13 -136.6(2) . . . . ?
N2 C7 C18 C17 -179.10(19) . . . . ?
N2 C7 C14 C15 178.7(2) . . . . ?
C16 C17 C18 C7 -0.2(3) . . . . ?
C16 C15 C14 C7 1.1(3) . . . . ?
C30 C29 C5 N3 -177.1(2) . . . . ?
C30 C29 C5 C33 0.4(3) . . . . ?
C30 C31 C32 C33 0.0(4) . . . . ?
C1 N1 C2 O1 -99.1(3) . . . . ?
C1 N1 C2 N3 85.9(3) . . . . ?
C1 N2 C7 C18 62.9(3) . . . . ?
C1 N2 C7 C14 -118.3(2) . . . . ?
C1 N2 C6 C19 42.4(3) . . . . ?
C1 N2 C6 C23 -138.9(2) . . . . ?
C1 C8 C9 C10 173.1(2) . . . . ?
C1 C8 C13 C12 -173.7(2) . . . . ?
C26 C27 C28 C4 0.6(3) . . . . ?
C8 C9 C10 C11 1.0(4) . . . . ?
C17 C16 C15 C14 0.7(3) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C7 N2 C1 N1 19.4(3) . . . . ?
C7 N2 C1 C8 -156.0(2) . . . . ?
C7 N2 C6 C19 -123.3(2) . . . . ?
C7 N2 C6 C23 55.4(3) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C13 C8 C9 C10 -1.5(3) . . . . ?
C13 C12 C11 C10 -1.1(4) . . . . ?
C6 N2 C1 N1 -146.3(2) . . . . ?
C6 N2 C1 C8 38.4(3) . . . . ?
C6 N2 C7 C18 -131.1(2) . . . . ?
C6 N2 C7 C14 47.8(3) . . . . ?
C6 C19 C20 C21 -1.0(3) . . . . ?
C6 C23 C22 C21 -0.6(4) . . . . ?
C18 C7 C14 C15 -2.5(3) . . . . ?
C27 C26 C25 C24 -1.0(3) . . . . ?
C27 C28 C4 N3 -179.32(19) . . . . ?
C27 C28 C4 C24 -0.7(3) . . . . ?
C2 N1 C1 N2 -175.00(19) . . . . ?
C2 N1 C1 C8 -0.1(3) . . . . ?
C2 N3 C5 C29 -136.1(2) . . . . ?
C2 N3 C5 C33 46.5(3) . . . . ?
C2 N3 C4 C24 75.0(3) . . . . ?
C2 N3 C4 C28 -106.4(2) . . . . ?
C25 C26 C27 C28 0.3(3) . . . . ?
C25 C24 C4 N3 178.57(19) . . . . ?
C25 C24 C4 C28 -0.1(3) . . . . ?
C20 C21 C22 C23 1.4(4) . . . . ?
C20 C19 C6 N2 -179.5(2) . . . . ?
C20 C19 C6 C23 1.8(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C22 C21 C20 C19 -0.6(4) . . . . ?
C22 C23 C6 N2 -179.7(2) . . . . ?
C22 C23 C6 C19 -1.0(3) . . . . ?
C29 C30 C31 C32 1.2(4) . . . . ?
C14 C7 C18 C17 2.0(3) . . . . ?
C31 C30 C29 C5 -1.4(4) . . . . ?
C32 C33 C5 N3 178.3(2) . . . . ?
C32 C33 C5 C29 0.8(3) . . . . ?
C5 N3 C2 O1 13.6(3) . . . . ?
C5 N3 C2 N1 -171.57(18) . . . . ?
C5 N3 C4 C24 -102.4(2) . . . . ?
C5 N3 C4 C28 76.2(3) . . . . ?
C5 C33 C32 C31 -1.0(4) . . . . ?
C4 N3 C2 O1 -163.7(2) . . . . ?
C4 N3 C2 N1 11.1(3) . . . . ?
C4 N3 C5 C29 41.3(3) . . . . ?
C4 N3 C5 C33 -136.1(2) . . . . ?
C4 C24 C25 C26 0.9(3) . . . . ?

####################################################################### 
# 
# 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_sas210
_database_code_depnum_ccdc_archive 'CCDC 1409105'
_audit_update_record             
;
2015-06-26 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-09-02
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C23 H23 N3 O'
_chemical_formula_sum            'C23 H23 N3 O'
_chemical_formula_weight         357.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H23 N3 O1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.1591(5)
_cell_length_b                   12.0853(10)
_cell_length_c                   12.7889(9)
_cell_angle_alpha                101.637(6)
_cell_angle_beta                 93.380(6)
_cell_angle_gamma                92.887(7)
_cell_volume                     928.85(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2156
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.4250
_cell_measurement_theta_min      3.4340
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0558
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7545
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.60
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -55.00  -28.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  101.0000  105.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   24.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339 -101.0000    1.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714 -101.0000    1.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   51.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339   57.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -87.00    3.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -57.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  6 omega  -90.00    1.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -38.0000   90.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega   16.00   67.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9714   38.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
  8 omega  -13.00   12.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0339  -99.0000   90.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0904563000
_diffrn_orient_matrix_UB_12      0.0293494000
_diffrn_orient_matrix_UB_13      0.0326041000
_diffrn_orient_matrix_UB_21      -0.0320992000
_diffrn_orient_matrix_UB_22      -0.0242502000
_diffrn_orient_matrix_UB_23      0.0432334000
_diffrn_orient_matrix_UB_31      0.0644238000
_diffrn_orient_matrix_UB_32      -0.0464319000
_diffrn_orient_matrix_UB_33      -0.0170414000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3285
_reflns_number_total             4080
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4080
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0585
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1019P)²+0.0576P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1728
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1 O 0.26089(18) 0.70239(9) 0.12959(9) 0.0149(3) Uani 1 1 d . . .
N1 N -0.0387(2) 0.66365(11) 0.21546(10) 0.0137(3) Uani 1 1 d . . .
N2 N 0.3220(2) 0.74701(11) 0.24360(10) 0.0134(3) Uani 1 1 d . . .
C14 C 0.3996(3) 1.03554(14) 0.17857(13) 0.0177(4) Uani 1 1 d . . .
H14 H 0.2688 1.0655 0.1992 0.021 Uiso 1 1 calc R . .
C65 C -0.1014(3) 0.80101(14) 0.41762(13) 0.0163(4) Uani 1 1 d . . .
H65 H -0.2118 0.7857 0.3630 0.020 Uiso 1 1 calc R . .
C10 C 0.6424(3) 0.88441(14) 0.16332(13) 0.0168(4) Uani 1 1 d . . .
H10 H 0.6769 0.8136 0.1748 0.020 Uiso 1 1 calc R . .
C9 C 0.4479(3) 0.92900(13) 0.19721(12) 0.0144(4) Uani 1 1 d . . .
N3 N -0.0573(2) 0.64082(12) 0.02735(11) 0.0187(3) Uani 1 1 d . . .
C75 C 0.4330(3) 0.53373(14) 0.28090(13) 0.0168(4) Uani 1 1 d . . .
H75 H 0.5307 0.5800 0.2537 0.020 Uiso 1 1 calc R . .
C1 C 0.1507(3) 0.68537(13) 0.29442(12) 0.0128(3) Uani 1 1 d . . .
C12 C 0.7373(3) 1.05187(16) 0.09639(14) 0.0231(4) Uani 1 1 d . . .
H12 H 0.8344 1.0928 0.0634 0.028 Uiso 1 1 calc R . .
C8 C 0.2943(3) 0.86967(13) 0.25865(13) 0.0142(3) Uani 1 1 d . . .
H8A H 0.3178 0.9036 0.3342 0.017 Uiso 1 1 calc R . .
H8B H 0.1455 0.8812 0.2359 0.017 Uiso 1 1 calc R . .
C64 C -0.1370(3) 0.86919(14) 0.51561(13) 0.0187(4) Uani 1 1 d . . .
H64 H -0.2720 0.8992 0.5264 0.022 Uiso 1 1 calc R . .
C63 C 0.0268(3) 0.89282(14) 0.59715(13) 0.0189(4) Uani 1 1 d . . .
H63 H 0.0031 0.9399 0.6620 0.023 Uiso 1 1 calc R . .
C7 C 0.2307(3) 0.57109(13) 0.30955(12) 0.0136(4) Uani 1 1 d . . .
C13 C 0.5447(3) 1.09719(15) 0.12957(14) 0.0211(4) Uani 1 1 d . . .
H13 H 0.5125 1.1687 0.1191 0.025 Uiso 1 1 calc R . .
C11 C 0.7849(3) 0.94547(15) 0.11242(13) 0.0201(4) Uani 1 1 d . . .
H11 H 0.9132 0.9146 0.0890 0.024 Uiso 1 1 calc R . .
C6 C 0.1000(3) 0.75573(13) 0.40161(12) 0.0136(4) Uani 1 1 d . . .
C72 C 0.1459(3) 0.39570(14) 0.36616(14) 0.0206(4) Uani 1 1 d . . .
H72 H 0.0503 0.3503 0.3955 0.025 Uiso 1 1 calc R . .
C2 C 0.0422(3) 0.66824(13) 0.12610(12) 0.0132(3) Uani 1 1 d . . .
C74 C 0.4886(3) 0.42616(15) 0.29330(14) 0.0211(4) Uani 1 1 d . . .
H74 H 0.6229 0.4006 0.2731 0.025 Uiso 1 1 calc R . .
C61 C 0.2625(3) 0.77693(14) 0.48510(13) 0.0171(4) Uani 1 1 d . . .
H61 H 0.3955 0.7444 0.4756 0.020 Uiso 1 1 calc R . .
C62 C 0.2269(3) 0.84602(14) 0.58197(13) 0.0196(4) Uani 1 1 d . . .
H62 H 0.3368 0.8611 0.6369 0.024 Uiso 1 1 calc R . .
C5 C -0.2821(3) 0.59418(15) 0.01368(14) 0.0205(4) Uani 1 1 d . . .
H5A H -0.3207 0.5708 0.0780 0.031 Uiso 1 1 calc R . .
H5B H -0.2973 0.5301 -0.0450 0.031 Uiso 1 1 calc R . .
H5C H -0.3767 0.6508 -0.0009 0.031 Uiso 1 1 calc R . .
C71 C 0.0895(3) 0.50178(14) 0.35308(13) 0.0174(4) Uani 1 1 d . . .
H71 H -0.0447 0.5271 0.3737 0.021 Uiso 1 1 calc R . .
C73 C 0.3460(3) 0.35741(14) 0.33520(14) 0.0214(4) Uani 1 1 d . . .
H73 H 0.3839 0.2857 0.3427 0.026 Uiso 1 1 calc R . .
C4 C 0.0417(3) 0.65972(16) -0.06822(14) 0.0227(4) Uani 1 1 d . . .
H4A H -0.0420 0.7106 -0.1004 0.034 Uiso 1 1 calc R . .
H4B H 0.0448 0.5889 -0.1181 0.034 Uiso 1 1 calc R . .
H4C H 0.1877 0.6922 -0.0495 0.034 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.4684(17) . ?
O1 C2 1.384(2) . ?
N1 C1 1.474(2) . ?
N1 C2 1.284(2) . ?
N2 C1 1.512(2) . ?
N2 C8 1.4757(19) . ?
C14 H14 0.9300 . ?
C14 C9 1.399(2) . ?
C14 C13 1.391(2) . ?
C65 H65 0.9300 . ?
C65 C64 1.390(2) . ?
C65 C6 1.390(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.394(2) . ?
C10 C11 1.391(2) . ?
C9 C8 1.508(2) . ?
N3 C2 1.342(2) . ?
N3 C5 1.456(2) . ?
N3 C4 1.450(2) . ?
C75 H75 0.9300 . ?
C75 C7 1.391(2) . ?
C75 C74 1.398(2) . ?
C1 C7 1.534(2) . ?
C1 C6 1.519(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(3) . ?
C12 C11 1.385(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C64 H64 0.9300 . ?
C64 C63 1.384(3) . ?
C63 H63 0.9300 . ?
C63 C62 1.389(2) . ?
C7 C71 1.393(2) . ?
C13 H13 0.9300 . ?
C11 H11 0.9300 . ?
C6 C61 1.395(2) . ?
C72 H72 0.9300 . ?
C72 C71 1.384(2) . ?
C72 C73 1.390(3) . ?
C74 H74 0.9300 . ?
C74 C73 1.382(3) . ?
C61 H61 0.9300 . ?
C61 C62 1.383(2) . ?
C62 H62 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C71 H71 0.9300 . ?
C73 H73 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N2 104.44(11) . . ?
C2 N1 C1 104.36(13) . . ?
O1 N2 C1 100.81(11) . . ?
O1 N2 C8 104.59(11) . . ?
C8 N2 C1 113.06(12) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C9 120.78(16) . . ?
C64 C65 H65 120.1 . . ?
C64 C65 C6 119.77(16) . . ?
C6 C65 H65 120.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C11 C10 C9 120.26(15) . . ?
C14 C9 C8 118.80(14) . . ?
C10 C9 C14 118.70(15) . . ?
C10 C9 C8 122.41(14) . . ?
C2 N3 C5 119.15(14) . . ?
C2 N3 C4 124.04(15) . . ?
C4 N3 C5 116.74(14) . . ?
C7 C75 H75 120.2 . . ?
C7 C75 C74 119.54(16) . . ?
C74 C75 H75 120.2 . . ?
N1 C1 N2 105.00(12) . . ?
N1 C1 C7 108.32(12) . . ?
N1 C1 C6 113.02(13) . . ?
N2 C1 C7 109.75(12) . . ?
N2 C1 C6 110.70(13) . . ?
C6 C1 C7 109.91(12) . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.89(17) . . ?
C11 C12 H12 120.1 . . ?
N2 C8 C9 113.14(13) . . ?
N2 C8 H8A 109.0 . . ?
N2 C8 H8B 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C65 C64 H64 119.8 . . ?
C63 C64 C65 120.47(16) . . ?
C63 C64 H64 119.8 . . ?
C64 C63 H63 120.1 . . ?
C64 C63 C62 119.85(15) . . ?
C62 C63 H63 120.1 . . ?
C75 C7 C1 123.46(15) . . ?
C75 C7 C71 119.28(14) . . ?
C71 C7 C1 117.25(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 C14 119.86(16) . . ?
C12 C13 H13 120.1 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.48(16) . . ?
C12 C11 H11 119.8 . . ?
C65 C6 C1 121.80(15) . . ?
C65 C6 C61 119.56(15) . . ?
C61 C6 C1 118.63(14) . . ?
C71 C72 H72 120.2 . . ?
C71 C72 C73 119.65(16) . . ?
C73 C72 H72 120.2 . . ?
N1 C2 O1 117.25(14) . . ?
N1 C2 N3 128.11(16) . . ?
N3 C2 O1 114.62(14) . . ?
C75 C74 H74 119.6 . . ?
C73 C74 C75 120.70(16) . . ?
C73 C74 H74 119.6 . . ?
C6 C61 H61 119.8 . . ?
C62 C61 C6 120.35(16) . . ?
C62 C61 H61 119.8 . . ?
C63 C62 H62 120.0 . . ?
C61 C62 C63 119.95(16) . . ?
C61 C62 H62 120.0 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C71 H71 119.5 . . ?
C72 C71 C7 120.99(16) . . ?
C72 C71 H71 119.5 . . ?
C72 C73 H73 120.1 . . ?
C74 C73 C72 119.80(15) . . ?
C74 C73 H73 120.1 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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
O1 N2 C1 N1 -28.12(13) . . . . ?
O1 N2 C1 C7 88.11(13) . . . . ?
O1 N2 C1 C6 -150.40(11) . . . . ?
O1 N2 C8 C9 -64.41(15) . . . . ?
N1 C1 C7 C75 114.86(17) . . . . ?
N1 C1 C7 C71 -64.26(18) . . . . ?
N1 C1 C6 C65 -4.8(2) . . . . ?
N1 C1 C6 C61 176.52(13) . . . . ?
N2 O1 C2 N1 -11.84(16) . . . . ?
N2 O1 C2 N3 169.93(12) . . . . ?
N2 C1 C7 C75 0.8(2) . . . . ?
N2 C1 C7 C71 -178.37(13) . . . . ?
N2 C1 C6 C65 112.65(16) . . . . ?
N2 C1 C6 C61 -66.02(17) . . . . ?
C14 C9 C8 N2 161.55(14) . . . . ?
C65 C64 C63 C62 -1.5(2) . . . . ?
C65 C6 C61 C62 -2.4(2) . . . . ?
C10 C9 C8 N2 -22.0(2) . . . . ?
C9 C14 C13 C12 1.5(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C75 C7 C71 C72 -1.3(2) . . . . ?
C75 C74 C73 C72 -0.5(3) . . . . ?
C1 N1 C2 O1 -6.85(17) . . . . ?
C1 N1 C2 N3 171.09(15) . . . . ?
C1 N2 C8 C9 -173.17(12) . . . . ?
C1 C7 C71 C72 177.85(15) . . . . ?
C1 C6 C61 C62 176.26(15) . . . . ?
C8 N2 C1 N1 82.99(14) . . . . ?
C8 N2 C1 C7 -160.79(12) . . . . ?
C8 N2 C1 C6 -39.29(17) . . . . ?
C64 C65 C6 C1 -177.05(14) . . . . ?
C64 C65 C6 C61 1.6(2) . . . . ?
C64 C63 C62 C61 0.7(3) . . . . ?
C7 C75 C74 C73 -1.0(3) . . . . ?
C7 C1 C6 C65 -125.95(16) . . . . ?
C7 C1 C6 C61 55.38(19) . . . . ?
C13 C14 C9 C10 -1.6(2) . . . . ?
C13 C14 C9 C8 175.02(15) . . . . ?
C13 C12 C11 C10 -1.1(3) . . . . ?
C11 C10 C9 C14 0.3(2) . . . . ?
C11 C10 C9 C8 -176.18(15) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C6 C65 C64 C63 0.3(2) . . . . ?
C6 C1 C7 C75 -121.22(17) . . . . ?
C6 C1 C7 C71 59.66(19) . . . . ?
C6 C61 C62 C63 1.3(3) . . . . ?
C2 O1 N2 C1 23.87(13) . . . . ?
C2 O1 N2 C8 -93.64(13) . . . . ?
C2 N1 C1 N2 22.18(14) . . . . ?
C2 N1 C1 C7 -95.02(14) . . . . ?
C2 N1 C1 C6 142.94(13) . . . . ?
C74 C75 C7 C1 -177.22(15) . . . . ?
C74 C75 C7 C71 1.9(2) . . . . ?
C5 N3 C2 O1 174.57(13) . . . . ?
C5 N3 C2 N1 -3.4(2) . . . . ?
C71 C72 C73 C74 1.1(3) . . . . ?
C73 C72 C71 C7 -0.2(3) . . . . ?
C4 N3 C2 O1 -8.6(2) . . . . ?
C4 N3 C2 N1 173.44(15) . . . . ?

####################################################################### 
# 
# 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_sas168
_database_code_depnum_ccdc_archive 'CCDC 1409781'
_audit_update_record             
;
2015-06-30 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2015-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N3 O'
_chemical_formula_sum            'C27 H23 N3 O'
_chemical_formula_weight         405.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 N O4 H10'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   22.9818(13)
_cell_length_b                   8.6205(3)
_cell_length_c                   23.3388(10)
_cell_angle_alpha                90
_cell_angle_beta                 114.188(6)
_cell_angle_gamma                90
_cell_volume                     4217.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8032
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.5810
_cell_measurement_theta_min      2.9730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            8727
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.626
_diffrn_reflns_v_R_equivalents   ?
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -12.00   20.25   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -94.00  -37.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000  -90.0000 76

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   80.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000 -150.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega   65.00   95.75   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega    3.00   64.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  120.0000 82

#__ type_ start__ end____ width___ exp.time_
  6 omega  -87.00  -36.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777 -178.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega  -10.00   41.00   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   77.0000    0.0000 68

#__ type_ start__ end____ width___ exp.time_
  8 omega   55.00   81.25   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   77.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega  -35.00  -21.50   0.7500   60.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000   30.0000 18
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0229836000
_diffrn_orient_matrix_UB_12      0.0237168000
_diffrn_orient_matrix_UB_13      0.0112388000
_diffrn_orient_matrix_UB_21      -0.0152367000
_diffrn_orient_matrix_UB_22      -0.0731655000
_diffrn_orient_matrix_UB_23      -0.0084176000
_diffrn_orient_matrix_UB_31      0.0195466000
_diffrn_orient_matrix_UB_32      -0.0292396000
_diffrn_orient_matrix_UB_33      0.0302361000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6768
_reflns_number_total             8727
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     562
_refine_ls_number_reflns         8727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1129
_refine_ls_R_factor_gt           0.0912
_refine_ls_restrained_S_all      1.115
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²+13.8748P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2150
_refine_ls_wR_factor_ref         0.2260
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.846(3) 0.154(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C18'(H18'), C19'(H19'), C27'(H27'), C28'(H28'), C11'(H11'), C26'(H26'),
 C20'(H20'), C12'(H12'), C16'(H16'), C21'(H21'), C24'(H24'), C25'(H25'),
 C23'(H23'), C8'(H8'), C13'(H13'), C15'(H15'), C9'(H9'), C22'(H22'), C14'(H14'),
  C17'(H17'), C19(H19), C18(H18), C28(H28), C21(H21), C24(H24), C25(H25),
 C26(H26), C22(H22), C27(H27), C8(H8), C23(H23), C20(H20), C13(H13), C11(H11),
 C12(H12), C17(H17), C9(H9), C14(H14), C16(H16), C15(H15)
3.b Idealised Me refined as rotating group:
 C10'(H10A,H10B,H10C), C10(H10D,H10E,H10F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1' O 0.77680(12) 0.1691(3) 0.91021(12) 0.0160(6) Uani 1 1 d . . . . .
N3' N 0.82954(15) 0.2809(4) 0.85643(14) 0.0153(7) Uani 1 1 d . . . . .
N1' N 0.87196(15) 0.0617(4) 0.92443(14) 0.0155(7) Uani 1 1 d . . . . .
N2' N 0.77865(15) 0.0207(4) 0.94162(14) 0.0151(7) Uani 1 1 d . . . . .
C7' C 0.88143(18) 0.0694(4) 1.03256(17) 0.0140(7) Uani 1 1 d . . . . .
C2' C 0.83050(18) 0.1662(4) 0.89731(17) 0.0150(8) Uani 1 1 d . . . . .
C1' C 0.84900(17) -0.0117(4) 0.96857(17) 0.0132(7) Uani 1 1 d . . . . .
C18' C 0.94287(19) 0.2575(5) 0.87483(18) 0.0194(8) Uani 1 1 d . . . . .
H18' H 0.9495 0.1849 0.9064 0.023 Uiso 1 1 calc R . . . .
C19' C 0.90312(18) -0.2546(5) 0.95415(17) 0.0176(8) Uani 1 1 d . . . . .
H19' H 0.9197 -0.1972 0.9306 0.021 Uiso 1 1 calc R . . . .
C4' C 0.76853(17) 0.3545(4) 0.82124(17) 0.0146(7) Uani 1 1 d . . . . .
C5' C 0.88282(19) 0.3213(4) 0.84302(17) 0.0156(8) Uani 1 1 d . . . . .
C10' C 0.74025(19) -0.0843(5) 0.89037(18) 0.0200(8) Uani 1 1 d . . . . .
H10A H 0.6979 -0.0432 0.8694 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.7382 -0.1846 0.9073 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.7595 -0.0936 0.8610 0.030 Uiso 1 1 calc GR . . . .
C27' C 0.9785(2) 0.1432(5) 1.11989(19) 0.0229(9) Uani 1 1 d . . . . .
H27' H 1.0229 0.1471 1.1385 0.027 Uiso 1 1 calc R . . . .
C28' C 0.94747(19) 0.0743(5) 1.06121(18) 0.0190(8) Uani 1 1 d . . . . .
H28' H 0.9712 0.0314 1.0411 0.023 Uiso 1 1 calc R . . . .
C11' C 0.65146(19) 0.4902(5) 0.75154(19) 0.0210(9) Uani 1 1 d . . . . .
H11' H 0.6123 0.5362 0.7280 0.025 Uiso 1 1 calc R . . . .
C6' C 0.86297(18) -0.1847(4) 0.97741(17) 0.0166(8) Uani 1 1 d . . . . .
C26' C 0.9438(2) 0.2058(5) 1.15065(18) 0.0214(9) Uani 1 1 d . . . . .
H26' H 0.9646 0.2504 1.1902 0.026 Uiso 1 1 calc R . . . .
C20' C 0.9187(2) -0.4118(5) 0.96617(19) 0.0232(9) Uani 1 1 d . . . . .
H20' H 0.9463 -0.4581 0.9513 0.028 Uiso 1 1 calc R . . . .
C12' C 0.6916(2) 0.5543(5) 0.8086(2) 0.0233(9) Uani 1 1 d . . . . .
H12' H 0.6789 0.6421 0.8236 0.028 Uiso 1 1 calc R . . . .
C16' C 0.9850(2) 0.4115(5) 0.8138(2) 0.0244(9) Uani 1 1 d . . . . .
H16' H 1.0189 0.4411 0.8043 0.029 Uiso 1 1 calc R . . . .
C21' C 0.8931(2) -0.4984(5) 1.00008(19) 0.0266(10) Uani 1 1 d . . . . .
H21' H 0.9032 -0.6030 1.0076 0.032 Uiso 1 1 calc R . . . .
C24' C 0.84681(19) 0.1341(5) 1.06315(18) 0.0205(8) Uani 1 1 d . . . . .
H24' H 0.8025 0.1324 1.0441 0.025 Uiso 1 1 calc R . . . .
C25' C 0.8777(2) 0.2015(5) 1.12203(19) 0.0229(9) Uani 1 1 d . . . . .
H25' H 0.8540 0.2439 1.1423 0.027 Uiso 1 1 calc R . . . .
C23' C 0.8382(2) -0.2718(5) 1.01261(18) 0.0212(9) Uani 1 1 d . . . . .
H23' H 0.8120 -0.2251 1.0292 0.025 Uiso 1 1 calc R . . . .
C8' C 0.72837(19) 0.2900(5) 0.76446(19) 0.0227(9) Uani 1 1 d . . . . .
H8' H 0.7406 0.2013 0.7496 0.027 Uiso 1 1 calc R . . . .
C13' C 0.75086(19) 0.4882(5) 0.84355(18) 0.0198(8) Uani 1 1 d . . . . .
H13' H 0.7783 0.5327 0.8813 0.024 Uiso 1 1 calc R . . . .
C15' C 0.9253(2) 0.4757(5) 0.7826(2) 0.0294(10) Uani 1 1 d . . . . .
H15' H 0.9190 0.5493 0.7515 0.035 Uiso 1 1 calc R . . . .
C9' C 0.6695(2) 0.3587(5) 0.72972(18) 0.0251(9) Uani 1 1 d . . . . .
H9' H 0.6423 0.3154 0.6916 0.030 Uiso 1 1 calc R . . . .
C22' C 0.8528(2) -0.4294(5) 1.0227(2) 0.0265(10) Uani 1 1 d . . . . .
H22' H 0.8351 -0.4882 1.0450 0.032 Uiso 1 1 calc R . . . .
C14' C 0.8744(2) 0.4328(5) 0.79662(19) 0.0236(9) Uani 1 1 d . . . . .
H14' H 0.8346 0.4781 0.7752 0.028 Uiso 1 1 calc R . . . .
C17' C 0.9932(2) 0.3010(5) 0.8601(2) 0.0243(9) Uani 1 1 d . . . . .
H17' H 1.0330 0.2557 0.8813 0.029 Uiso 1 1 calc R . . . .
O1 O 0.91678(13) 0.1503(3) 0.27476(12) 0.0163(6) Uani 1 1 d . . . . .
N1 N 0.92908(15) 0.0495(4) 0.36898(14) 0.0145(6) Uani 1 1 d . . . . .
N3 N 0.85979(15) 0.2650(4) 0.32376(14) 0.0166(7) Uani 1 1 d . . . . .
N2 N 0.95063(15) 0.0021(4) 0.27965(14) 0.0151(7) Uani 1 1 d . . . . .
C2 C 0.90181(18) 0.1499(4) 0.32610(16) 0.0143(7) Uani 1 1 d . . . . .
C1 C 0.97582(18) -0.0244(4) 0.34926(17) 0.0145(8) Uani 1 1 d . . . . .
C7 C 0.98464(18) -0.1962(4) 0.36576(17) 0.0162(8) Uani 1 1 d . . . . .
C4 C 0.82565(18) 0.3408(4) 0.26331(17) 0.0167(8) Uani 1 1 d . . . . .
C6 C 1.03967(18) 0.0595(4) 0.38161(17) 0.0143(7) Uani 1 1 d . . . . .
C19 C 1.07286(19) 0.1211(5) 0.34880(19) 0.0196(8) Uani 1 1 d . . . . .
H19 H 1.0557 0.1142 0.3052 0.024 Uiso 1 1 calc R . . . .
C5 C 0.84626(18) 0.3125(4) 0.37574(17) 0.0159(8) Uani 1 1 d . . . . .
C18 C 0.87477(19) 0.2447(5) 0.43460(18) 0.0199(8) Uani 1 1 d . . . . .
H18 H 0.9033 0.1632 0.4412 0.024 Uiso 1 1 calc R . . . .
C28 C 1.02294(19) -0.2866(5) 0.34529(18) 0.0198(8) Uani 1 1 d . . . . .
H28 H 1.0420 -0.2423 0.3210 0.024 Uiso 1 1 calc R . . . .
C21 C 1.1573(2) 0.2053(5) 0.4452(2) 0.0246(9) Uani 1 1 d . . . . .
H21 H 1.1964 0.2540 0.4663 0.030 Uiso 1 1 calc R . . . .
C24 C 0.95735(18) -0.2633(5) 0.40316(17) 0.0170(8) Uani 1 1 d . . . . .
H24 H 0.9320 -0.2039 0.4171 0.020 Uiso 1 1 calc R . . . .
C25 C 0.9680(2) -0.4197(5) 0.41973(19) 0.0245(9) Uani 1 1 d . . . . .
H25 H 0.9499 -0.4641 0.4448 0.029 Uiso 1 1 calc R . . . .
C26 C 1.0056(2) -0.5090(5) 0.39895(19) 0.0265(10) Uani 1 1 d . . . . .
H26 H 1.0128 -0.6130 0.4102 0.032 Uiso 1 1 calc R . . . .
C22 C 1.1242(2) 0.1440(5) 0.47854(19) 0.0244(9) Uani 1 1 d . . . . .
H22 H 1.1414 0.1515 0.5221 0.029 Uiso 1 1 calc R . . . .
C27 C 1.0325(2) -0.4433(5) 0.36137(19) 0.0255(9) Uani 1 1 d . . . . .
H27 H 1.0570 -0.5039 0.3468 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8534(2) 0.4624(5) 0.24521(18) 0.0229(9) Uani 1 1 d . . . . .
H8 H 0.8942 0.4962 0.2710 0.027 Uiso 1 1 calc R . . . .
C23 C 1.06598(19) 0.0724(5) 0.44721(18) 0.0189(8) Uani 1 1 d . . . . .
H23 H 1.0441 0.0325 0.4698 0.023 Uiso 1 1 calc R . . . .
C10 C 0.90010(19) -0.1063(5) 0.24160(18) 0.0198(8) Uani 1 1 d . . . . .
H10D H 0.8703 -0.1193 0.2604 0.030 Uiso 1 1 calc GR . . . .
H10E H 0.9187 -0.2048 0.2397 0.030 Uiso 1 1 calc GR . . . .
H10F H 0.8784 -0.0655 0.1999 0.030 Uiso 1 1 calc GR . . . .
C20 C 1.1313(2) 0.1929(5) 0.38055(19) 0.0214(9) Uani 1 1 d . . . . .
H20 H 1.1533 0.2331 0.3581 0.026 Uiso 1 1 calc R . . . .
C13 C 0.7645(2) 0.2928(6) 0.2263(2) 0.0277(10) Uani 1 1 d . . . . .
H13 H 0.7460 0.2121 0.2393 0.033 Uiso 1 1 calc R . . . .
C11 C 0.7577(2) 0.4862(5) 0.14951(19) 0.0255(9) Uani 1 1 d . . . . .
H11 H 0.7351 0.5349 0.1112 0.031 Uiso 1 1 calc R . . . .
C12 C 0.7306(2) 0.3671(6) 0.1687(2) 0.0338(11) Uani 1 1 d . . . . .
H12 H 0.6893 0.3352 0.1434 0.041 Uiso 1 1 calc R . . . .
C17 C 0.8609(2) 0.2978(5) 0.48362(18) 0.0224(9) Uani 1 1 d . . . . .
H17 H 0.8806 0.2515 0.5229 0.027 Uiso 1 1 calc R . . . .
C9 C 0.8188(2) 0.5336(5) 0.18736(19) 0.0273(10) Uani 1 1 d . . . . .
H9 H 0.8373 0.6141 0.1742 0.033 Uiso 1 1 calc R . . . .
C14 C 0.8041(3) 0.4339(6) 0.3673(2) 0.0405(13) Uani 1 1 d . . . . .
H14 H 0.7843 0.4802 0.3280 0.049 Uiso 1 1 calc R . . . .
C16 C 0.8191(2) 0.4169(6) 0.4753(2) 0.0317(11) Uani 1 1 d . . . . .
H16 H 0.8094 0.4502 0.5083 0.038 Uiso 1 1 calc R . . . .
C15 C 0.7911(3) 0.4872(7) 0.4170(3) 0.0535(17) Uani 1 1 d . . . . .
H15 H 0.7636 0.5706 0.4110 0.064 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1' N2' 1.467(4) . ?
O1' C2' 1.385(4) . ?
N3' C2' 1.368(5) . ?
N3' C4' 1.449(5) . ?
N3' C5' 1.426(5) . ?
N1' C2' 1.275(5) . ?
N1' C1' 1.478(5) . ?
N2' C1' 1.501(5) . ?
N2' C10' 1.471(5) . ?
C7' C1' 1.537(5) . ?
C7' C28' 1.386(5) . ?
C7' C24' 1.385(5) . ?
C1' C6' 1.522(5) . ?
C18' H18' 0.9300 . ?
C18' C5' 1.385(6) . ?
C18' C17' 1.387(6) . ?
C19' H19' 0.9300 . ?
C19' C6' 1.385(5) . ?
C19' C20' 1.400(6) . ?
C4' C8' 1.384(5) . ?
C4' C13' 1.393(5) . ?
C5' C14' 1.401(5) . ?
C10' H10A 0.9600 . ?
C10' H10B 0.9600 . ?
C10' H10C 0.9600 . ?
C27' H27' 0.9300 . ?
C27' C28' 1.392(6) . ?
C27' C26' 1.382(6) . ?
C28' H28' 0.9300 . ?
C11' H11' 0.9300 . ?
C11' C12' 1.387(6) . ?
C11' C9' 1.375(6) . ?
C6' C23' 1.396(6) . ?
C26' H26' 0.9300 . ?
C26' C25' 1.388(6) . ?
C20' H20' 0.9300 . ?
C20' C21' 1.381(6) . ?
C12' H12' 0.9300 . ?
C12' C13' 1.390(6) . ?
C16' H16' 0.9300 . ?
C16' C15' 1.378(6) . ?
C16' C17' 1.393(6) . ?
C21' H21' 0.9300 . ?
C21' C22' 1.376(7) . ?
C24' H24' 0.9300 . ?
C24' C25' 1.390(6) . ?
C25' H25' 0.9300 . ?
C23' H23' 0.9300 . ?
C23' C22' 1.396(6) . ?
C8' H8' 0.9300 . ?
C8' C9' 1.392(6) . ?
C13' H13' 0.9300 . ?
C15' H15' 0.9300 . ?
C15' C14' 1.387(6) . ?
C9' H9' 0.9300 . ?
C22' H22' 0.9300 . ?
C14' H14' 0.9300 . ?
C17' H17' 0.9300 . ?
O1 N2 1.476(4) . ?
O1 C2 1.375(4) . ?
N1 C2 1.276(5) . ?
N1 C1 1.475(5) . ?
N3 C2 1.370(5) . ?
N3 C4 1.458(5) . ?
N3 C5 1.430(5) . ?
N2 C1 1.502(5) . ?
N2 C10 1.472(5) . ?
C1 C7 1.523(5) . ?
C1 C6 1.529(5) . ?
C7 C28 1.398(5) . ?
C7 C24 1.392(5) . ?
C4 C8 1.380(6) . ?
C4 C13 1.377(6) . ?
C6 C19 1.389(5) . ?
C6 C23 1.401(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.386(6) . ?
C5 C18 1.386(5) . ?
C5 C14 1.385(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.385(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.395(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.396(6) . ?
C21 C20 1.380(6) . ?
C24 H24 0.9300 . ?
C24 C25 1.396(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.384(6) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.379(6) . ?
C27 H27 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.397(6) . ?
C23 H23 0.9300 . ?
C10 H10D 0.9600 . ?
C10 H10E 0.9600 . ?
C10 H10F 0.9600 . ?
C20 H20 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.402(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(7) . ?
C11 C9 1.379(6) . ?
C12 H12 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.366(6) . ?
C9 H9 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.388(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(7) . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2' O1' N2' 104.3(3) . . ?
C2' N3' C4' 116.6(3) . . ?
C2' N3' C5' 124.0(3) . . ?
C5' N3' C4' 119.2(3) . . ?
C2' N1' C1' 103.9(3) . . ?
O1' N2' C1' 100.2(3) . . ?
O1' N2' C10' 104.2(3) . . ?
C10' N2' C1' 114.3(3) . . ?
C28' C7' C1' 118.8(3) . . ?
C24' C7' C1' 122.1(3) . . ?
C24' C7' C28' 119.1(4) . . ?
N3' C2' O1' 112.2(3) . . ?
N1' C2' O1' 117.1(3) . . ?
N1' C2' N3' 130.7(4) . . ?
N1' C1' N2' 105.0(3) . . ?
N1' C1' C7' 108.3(3) . . ?
N1' C1' C6' 113.5(3) . . ?
N2' C1' C7' 109.4(3) . . ?
N2' C1' C6' 111.7(3) . . ?
C6' C1' C7' 108.8(3) . . ?
C5' C18' H18' 119.7 . . ?
C5' C18' C17' 120.6(4) . . ?
C17' C18' H18' 119.7 . . ?
C6' C19' H19' 120.1 . . ?
C6' C19' C20' 119.9(4) . . ?
C20' C19' H19' 120.1 . . ?
C8' C4' N3' 118.6(3) . . ?
C8' C4' C13' 120.6(4) . . ?
C13' C4' N3' 120.9(3) . . ?
C18' C5' N3' 122.8(3) . . ?
C18' C5' C14' 118.6(4) . . ?
C14' C5' N3' 118.6(3) . . ?
N2' C10' H10A 109.5 . . ?
N2' C10' H10B 109.5 . . ?
N2' C10' H10C 109.5 . . ?
H10A C10' H10B 109.5 . . ?
H10A C10' H10C 109.5 . . ?
H10B C10' H10C 109.5 . . ?
C28' C27' H27' 119.8 . . ?
C26' C27' H27' 119.8 . . ?
C26' C27' C28' 120.4(4) . . ?
C7' C28' C27' 120.4(4) . . ?
C7' C28' H28' 119.8 . . ?
C27' C28' H28' 119.8 . . ?
C12' C11' H11' 120.0 . . ?
C9' C11' H11' 120.0 . . ?
C9' C11' C12' 120.1(4) . . ?
C19' C6' C1' 120.7(3) . . ?
C19' C6' C23' 119.7(4) . . ?
C23' C6' C1' 119.5(4) . . ?
C27' C26' H26' 120.3 . . ?
C27' C26' C25' 119.4(4) . . ?
C25' C26' H26' 120.3 . . ?
C19' C20' H20' 119.8 . . ?
C21' C20' C19' 120.3(4) . . ?
C21' C20' H20' 119.8 . . ?
C11' C12' H12' 119.8 . . ?
C11' C12' C13' 120.4(4) . . ?
C13' C12' H12' 119.8 . . ?
C15' C16' H16' 120.8 . . ?
C15' C16' C17' 118.3(4) . . ?
C17' C16' H16' 120.8 . . ?
C20' C21' H21' 120.1 . . ?
C22' C21' C20' 119.8(4) . . ?
C22' C21' H21' 120.1 . . ?
C7' C24' H24' 119.7 . . ?
C7' C24' C25' 120.6(4) . . ?
C25' C24' H24' 119.7 . . ?
C26' C25' C24' 120.2(4) . . ?
C26' C25' H25' 119.9 . . ?
C24' C25' H25' 119.9 . . ?
C6' C23' H23' 120.2 . . ?
C6' C23' C22' 119.6(4) . . ?
C22' C23' H23' 120.2 . . ?
C4' C8' H8' 120.2 . . ?
C4' C8' C9' 119.6(4) . . ?
C9' C8' H8' 120.2 . . ?
C4' C13' H13' 120.5 . . ?
C12' C13' C4' 119.0(4) . . ?
C12' C13' H13' 120.5 . . ?
C16' C15' H15' 119.3 . . ?
C16' C15' C14' 121.4(4) . . ?
C14' C15' H15' 119.3 . . ?
C11' C9' C8' 120.2(4) . . ?
C11' C9' H9' 119.9 . . ?
C8' C9' H9' 119.9 . . ?
C21' C22' C23' 120.6(4) . . ?
C21' C22' H22' 119.7 . . ?
C23' C22' H22' 119.7 . . ?
C5' C14' H14' 119.9 . . ?
C15' C14' C5' 120.2(4) . . ?
C15' C14' H14' 119.9 . . ?
C18' C17' C16' 121.0(4) . . ?
C18' C17' H17' 119.5 . . ?
C16' C17' H17' 119.5 . . ?
C2 O1 N2 104.0(3) . . ?
C2 N1 C1 103.6(3) . . ?
C2 N3 C4 117.0(3) . . ?
C2 N3 C5 124.6(3) . . ?
C5 N3 C4 118.3(3) . . ?
O1 N2 C1 99.9(2) . . ?
C10 N2 O1 104.0(3) . . ?
C10 N2 C1 114.5(3) . . ?
N1 C2 O1 117.9(3) . . ?
N1 C2 N3 129.3(3) . . ?
N3 C2 O1 112.8(3) . . ?
N1 C1 N2 105.3(3) . . ?
N1 C1 C7 112.3(3) . . ?
N1 C1 C6 108.4(3) . . ?
N2 C1 C7 111.9(3) . . ?
N2 C1 C6 109.2(3) . . ?
C7 C1 C6 109.5(3) . . ?
C28 C7 C1 119.5(3) . . ?
C24 C7 C1 121.0(3) . . ?
C24 C7 C28 119.4(4) . . ?
C8 C4 N3 120.3(3) . . ?
C13 C4 N3 118.6(4) . . ?
C13 C4 C8 121.1(4) . . ?
C19 C6 C1 122.8(3) . . ?
C19 C6 C23 118.9(4) . . ?
C23 C6 C1 118.3(3) . . ?
C6 C19 H19 119.8 . . ?
C20 C19 C6 120.5(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C5 N3 122.8(3) . . ?
C14 C5 N3 118.6(3) . . ?
C14 C5 C18 118.6(4) . . ?
C5 C18 H18 119.8 . . ?
C17 C18 C5 120.3(4) . . ?
C17 C18 H18 119.8 . . ?
C7 C28 H28 120.0 . . ?
C27 C28 C7 119.9(4) . . ?
C27 C28 H28 120.0 . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.3(4) . . ?
C7 C24 H24 120.0 . . ?
C7 C24 C25 120.1(4) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.3(4) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 119.9(4) . . ?
C27 C26 H26 120.0 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.4(4) . . ?
C23 C22 H22 119.8 . . ?
C28 C27 H27 119.8 . . ?
C26 C27 C28 120.3(4) . . ?
C26 C27 H27 119.8 . . ?
C4 C8 H8 120.7 . . ?
C4 C8 C9 118.6(4) . . ?
C9 C8 H8 120.7 . . ?
C6 C23 H23 119.8 . . ?
C22 C23 C6 120.3(4) . . ?
C22 C23 H23 119.8 . . ?
N2 C10 H10D 109.5 . . ?
N2 C10 H10E 109.5 . . ?
N2 C10 H10F 109.5 . . ?
H10D C10 H10E 109.5 . . ?
H10D C10 H10F 109.5 . . ?
H10E C10 H10F 109.5 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.6(4) . . ?
C21 C20 H20 119.7 . . ?
C4 C13 H13 120.4 . . ?
C4 C13 C12 119.3(4) . . ?
C12 C13 H13 120.4 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C9 119.6(4) . . ?
C9 C11 H11 120.2 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(4) . . ?
C11 C12 H12 119.8 . . ?
C18 C17 H17 119.4 . . ?
C16 C17 C18 121.2(4) . . ?
C16 C17 H17 119.4 . . ?
C8 C9 H9 119.5 . . ?
C11 C9 C8 121.0(4) . . ?
C11 C9 H9 119.5 . . ?
C5 C14 H14 119.7 . . ?
C5 C14 C15 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C17 C16 H16 120.5 . . ?
C17 C16 C15 119.0(4) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(4) . . ?
C16 C15 H15 119.8 . . ?

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
O1' N2' C1' N1' -30.1(3) . . . . ?
O1' N2' C1' C7' 85.9(3) . . . . ?
O1' N2' C1' C6' -153.5(3) . . . . ?
N3' C4' C8' C9' -179.9(4) . . . . ?
N3' C4' C13' C12' -179.4(4) . . . . ?
N3' C5' C14' C15' 179.6(4) . . . . ?
N1' C1' C6' C19' 10.6(5) . . . . ?
N1' C1' C6' C23' -173.3(3) . . . . ?
N2' O1' C2' N3' 167.2(3) . . . . ?
N2' O1' C2' N1' -13.2(4) . . . . ?
N2' C1' C6' C19' 129.1(4) . . . . ?
N2' C1' C6' C23' -54.9(4) . . . . ?
C7' C1' C6' C19' -110.0(4) . . . . ?
C7' C1' C6' C23' 66.1(4) . . . . ?
C7' C24' C25' C26' 0.5(6) . . . . ?
C2' O1' N2' C1' 25.8(3) . . . . ?
C2' O1' N2' C10' -92.6(3) . . . . ?
C2' N3' C4' C8' -88.4(4) . . . . ?
C2' N3' C4' C13' 92.4(4) . . . . ?
C2' N3' C5' C18' -6.3(6) . . . . ?
C2' N3' C5' C14' 175.1(4) . . . . ?
C2' N1' C1' N2' 23.6(4) . . . . ?
C2' N1' C1' C7' -93.2(3) . . . . ?
C2' N1' C1' C6' 145.9(3) . . . . ?
C1' N1' C2' O1' -6.8(4) . . . . ?
C1' N1' C2' N3' 172.8(4) . . . . ?
C1' C7' C28' C27' -178.3(3) . . . . ?
C1' C7' C24' C25' 177.6(4) . . . . ?
C1' C6' C23' C22' -177.7(4) . . . . ?
C18' C5' C14' C15' 0.9(6) . . . . ?
C19' C6' C23' C22' -1.6(6) . . . . ?
C19' C20' C21' C22' -0.7(6) . . . . ?
C4' N3' C2' O1' -16.4(4) . . . . ?
C4' N3' C2' N1' 164.0(4) . . . . ?
C4' N3' C5' C18' 179.4(3) . . . . ?
C4' N3' C5' C14' 0.8(5) . . . . ?
C4' C8' C9' C11' 0.2(6) . . . . ?
C5' N3' C2' O1' 169.2(3) . . . . ?
C5' N3' C2' N1' -10.4(6) . . . . ?
C5' N3' C4' C8' 86.3(4) . . . . ?
C5' N3' C4' C13' -92.9(4) . . . . ?
C5' C18' C17' C16' 1.1(6) . . . . ?
C10' N2' C1' N1' 80.6(4) . . . . ?
C10' N2' C1' C7' -163.4(3) . . . . ?
C10' N2' C1' C6' -42.8(4) . . . . ?
C27' C26' C25' C24' 0.3(6) . . . . ?
C28' C7' C1' N1' -56.4(4) . . . . ?
C28' C7' C1' N2' -170.3(3) . . . . ?
C28' C7' C1' C6' 67.4(4) . . . . ?
C28' C7' C24' C25' -0.7(6) . . . . ?
C28' C27' C26' C25' -1.0(6) . . . . ?
C11' C12' C13' C4' -1.7(6) . . . . ?
C6' C19' C20' C21' 1.3(6) . . . . ?
C6' C23' C22' C21' 2.2(6) . . . . ?
C26' C27' C28' C7' 0.8(6) . . . . ?
C20' C19' C6' C1' 175.9(3) . . . . ?
C20' C19' C6' C23' -0.1(6) . . . . ?
C20' C21' C22' C23' -1.0(6) . . . . ?
C12' C11' C9' C8' -0.5(6) . . . . ?
C16' C15' C14' C5' -0.4(7) . . . . ?
C24' C7' C1' N1' 125.3(4) . . . . ?
C24' C7' C1' N2' 11.4(5) . . . . ?
C24' C7' C1' C6' -111.0(4) . . . . ?
C24' C7' C28' C27' 0.1(6) . . . . ?
C8' C4' C13' C12' 1.4(6) . . . . ?
C13' C4' C8' C9' -0.7(6) . . . . ?
C15' C16' C17' C18' -0.6(7) . . . . ?
C9' C11' C12' C13' 1.3(6) . . . . ?
C17' C18' C5' N3' -179.9(4) . . . . ?
C17' C18' C5' C14' -1.3(6) . . . . ?
C17' C16' C15' C14' 0.3(7) . . . . ?
O1 N2 C1 N1 29.9(3) . . . . ?
O1 N2 C1 C7 152.2(3) . . . . ?
O1 N2 C1 C6 -86.4(3) . . . . ?
N1 C1 C7 C28 174.3(3) . . . . ?
N1 C1 C7 C24 -8.5(5) . . . . ?
N1 C1 C6 C19 -126.1(4) . . . . ?
N1 C1 C6 C23 54.8(4) . . . . ?
N3 C4 C8 C9 -179.1(4) . . . . ?
N3 C4 C13 C12 178.5(4) . . . . ?
N3 C5 C18 C17 178.5(4) . . . . ?
N3 C5 C14 C15 -177.9(5) . . . . ?
N2 O1 C2 N1 13.3(4) . . . . ?
N2 O1 C2 N3 -168.6(3) . . . . ?
N2 C1 C7 C28 56.0(4) . . . . ?
N2 C1 C7 C24 -126.8(4) . . . . ?
N2 C1 C6 C19 -11.8(5) . . . . ?
N2 C1 C6 C23 169.1(3) . . . . ?
C2 O1 N2 C1 -25.6(3) . . . . ?
C2 O1 N2 C10 92.9(3) . . . . ?
C2 N1 C1 N2 -23.3(4) . . . . ?
C2 N1 C1 C7 -145.4(3) . . . . ?
C2 N1 C1 C6 93.5(3) . . . . ?
C2 N3 C4 C8 -84.6(5) . . . . ?
C2 N3 C4 C13 98.2(5) . . . . ?
C2 N3 C5 C18 -0.3(6) . . . . ?
C2 N3 C5 C14 178.0(4) . . . . ?
C1 N1 C2 O1 6.4(4) . . . . ?
C1 N1 C2 N3 -171.2(4) . . . . ?
C1 C7 C28 C27 178.5(3) . . . . ?
C1 C7 C24 C25 -177.5(3) . . . . ?
C1 C6 C19 C20 -178.5(4) . . . . ?
C1 C6 C23 C22 178.6(4) . . . . ?
C7 C1 C6 C19 111.0(4) . . . . ?
C7 C1 C6 C23 -68.1(4) . . . . ?
C7 C28 C27 C26 -1.7(6) . . . . ?
C7 C24 C25 C26 -0.2(6) . . . . ?
C4 N3 C2 O1 15.2(5) . . . . ?
C4 N3 C2 N1 -167.0(4) . . . . ?
C4 N3 C5 C18 178.1(4) . . . . ?
C4 N3 C5 C14 -3.6(6) . . . . ?
C4 C8 C9 C11 1.4(6) . . . . ?
C4 C13 C12 C11 -0.2(7) . . . . ?
C6 C1 C7 C28 -65.2(4) . . . . ?
C6 C1 C7 C24 112.0(4) . . . . ?
C6 C19 C20 C21 -0.5(6) . . . . ?
C19 C6 C23 C22 -0.6(6) . . . . ?
C5 N3 C2 O1 -166.3(3) . . . . ?
C5 N3 C2 N1 11.5(6) . . . . ?
C5 N3 C4 C8 96.9(5) . . . . ?
C5 N3 C4 C13 -80.4(5) . . . . ?
C5 C18 C17 C16 0.3(7) . . . . ?
C5 C14 C15 C16 -1.6(10) . . . . ?
C18 C5 C14 C15 0.5(8) . . . . ?
C18 C17 C16 C15 -1.4(8) . . . . ?
C28 C7 C24 C25 -0.3(6) . . . . ?
C21 C22 C23 C6 0.4(6) . . . . ?
C24 C7 C28 C27 1.3(6) . . . . ?
C24 C25 C26 C27 -0.3(6) . . . . ?
C25 C26 C27 C28 1.2(6) . . . . ?
C22 C21 C20 C19 0.3(6) . . . . ?
C8 C4 C13 C12 1.3(7) . . . . ?
C23 C6 C19 C20 0.6(6) . . . . ?
C10 N2 C1 N1 -80.6(4) . . . . ?
C10 N2 C1 C7 41.7(4) . . . . ?
C10 N2 C1 C6 163.1(3) . . . . ?
C20 C21 C22 C23 -0.3(6) . . . . ?
C13 C4 C8 C9 -1.9(6) . . . . ?
C12 C11 C9 C8 -0.4(7) . . . . ?
C17 C16 C15 C14 2.0(9) . . . . ?
C9 C11 C12 C13 -0.3(7) . . . . ?
C14 C5 C18 C17 0.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.846(3)
2 0.154(3)

####################################################################### 
# 
# 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_sas98_2
_database_code_depnum_ccdc_archive 'CCDC 1409782'
_audit_update_record             
;
2015-07-02 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2015-07-01
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N3 O'
_chemical_formula_sum            'C22 H21 N3 O'
_chemical_formula_weight         343.42
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H21 N3 O1'
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_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.1527(8)
_cell_length_b                   10.0852(7)
_cell_length_c                   10.4387(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.242(10)
_cell_angle_gamma                90
_cell_volume                     904.06(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2441
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9610
_cell_measurement_theta_min      5.1360
_exptl_absorpt_coefficient_mu    0.623
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68670
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7495
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.482
_diffrn_reflns_theta_min         4.515
_diffrn_ambient_temperature      100.00(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.9857
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -46.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   30.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega  -73.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  -90.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega   60.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   66.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   32.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 11 omega   66.00   93.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   72.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  120.0000 37

#__ type_ start__ end____ width___ exp.time_
 13 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   71.00  101.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 15 omega  151.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
 17 omega   46.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega  118.00  145.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega  152.00  177.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 20 omega   36.00   89.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 21 omega   77.00  131.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -180.0000 54

#__ type_ start__ end____ width___ exp.time_
 22 omega   40.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -33.0000  156.0000 25

#__ type_ start__ end____ width___ exp.time_
 23 omega   40.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega  108.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   30.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 25 omega  149.00  176.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   15.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 26 omega  137.00  167.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 27 omega -109.00  -50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -38.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
 28 omega -118.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000   60.0000 106

#__ type_ start__ end____ width___ exp.time_
 29 omega   58.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 30 omega   11.00   39.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   57.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
 31 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   80.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 33 omega  117.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -14.0000 -120.9673 27

#__ type_ start__ end____ width___ exp.time_
 34 omega  144.00  169.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 35 omega  127.00  162.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 36 omega   80.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 37 omega  153.00  178.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 38 omega   83.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 39 omega   85.00  112.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1058910000
_diffrn_orient_matrix_UB_12      -0.0362917000
_diffrn_orient_matrix_UB_13      -0.0817394000
_diffrn_orient_matrix_UB_21      0.1238711000
_diffrn_orient_matrix_UB_22      -0.0529438000
_diffrn_orient_matrix_UB_23      0.1313131000
_diffrn_orient_matrix_UB_31      -0.0750040000
_diffrn_orient_matrix_UB_32      -0.1385858000
_diffrn_orient_matrix_UB_33      -0.0288264000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.724
_reflns_Friedel_fraction_full    0.842
_reflns_Friedel_fraction_max     0.815
_reflns_number_gt                2797
_reflns_number_total             3270
_reflns_odcompleteness_completeness 94.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.0714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.0994
_refine_special_details          ?
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2458(3) 0.2699(2) 0.5814(2) 0.0277(5) Uani 1 1 d . . . . .
N2 N 0.2494(3) 0.4998(3) 0.7917(2) 0.0209(5) Uani 1 1 d . . . . .
N1 N 0.0469(3) 0.3817(3) 0.6235(2) 0.0224(5) Uani 1 1 d . . . . .
C8 C 0.0045(3) 0.4400(3) 0.8266(3) 0.0209(6) Uani 1 1 d . . . . .
C1 C 0.1065(3) 0.4372(3) 0.7410(3) 0.0218(6) Uani 1 1 d . . . . .
C6 C 0.3178(3) 0.5595(3) 0.6993(3) 0.0213(6) Uani 1 1 d . . . . .
N3 N 0.0820(3) 0.4006(3) 0.4142(3) 0.0252(6) Uani 1 1 d . . . . .
C17 C 0.5210(4) 0.6043(4) 1.1337(3) 0.0280(7) Uani 1 1 d . . . . .
H17 H 0.5820 0.6772 1.1734 0.034 Uiso 1 1 calc R . . . .
C2 C 0.1380(3) 0.3488(3) 0.5420(3) 0.0213(6) Uani 1 1 d . . . . .
C15 C 0.4291(4) 0.3848(4) 1.1518(3) 0.0273(7) Uani 1 1 d . . . . .
H15 H 0.4274 0.3107 1.2043 0.033 Uiso 1 1 calc R . . . .
C21 C 0.4511(4) 0.6781(4) 0.5264(3) 0.0285(7) Uani 1 1 d . . . . .
H21 H 0.4955 0.7179 0.4684 0.034 Uiso 1 1 calc R . . . .
C9 C -0.0919(3) 0.3316(3) 0.8215(3) 0.0244(6) Uani 1 1 d . . . . .
H9 H -0.0884 0.2582 0.7687 0.029 Uiso 1 1 calc R . . . .
C4 C -0.0410(4) 0.4980(4) 0.3702(3) 0.0285(7) Uani 1 1 d . . . . .
H4A H -0.0950 0.5011 0.4343 0.043 Uiso 1 1 calc GR . . . .
H4B H -0.1126 0.4741 0.2818 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.0029 0.5835 0.3654 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.5252(4) 0.5722(3) 0.6082(3) 0.0286(7) Uani 1 1 d . . . . .
H22 H 0.6196 0.5415 0.6050 0.034 Uiso 1 1 calc R . . . .
C18 C 0.4323(3) 0.6061(3) 0.9952(3) 0.0237(6) Uani 1 1 d . . . . .
H18 H 0.4335 0.6807 0.9433 0.028 Uiso 1 1 calc R . . . .
C11 C -0.2005(4) 0.4407(4) 0.9721(3) 0.0310(7) Uani 1 1 d . . . . .
H11 H -0.2687 0.4411 1.0206 0.037 Uiso 1 1 calc R . . . .
C19 C 0.2442(4) 0.6655(3) 0.6193(3) 0.0238(6) Uani 1 1 d . . . . .
H19 H 0.1508 0.6977 0.6238 0.029 Uiso 1 1 calc R . . . .
C10 C -0.1929(4) 0.3322(4) 0.8942(3) 0.0271(7) Uani 1 1 d . . . . .
H10 H -0.2560 0.2590 0.8905 0.032 Uiso 1 1 calc R . . . .
C16 C 0.5189(4) 0.4946(4) 1.2124(3) 0.0293(7) Uani 1 1 d . . . . .
H16 H 0.5770 0.4940 1.3052 0.035 Uiso 1 1 calc R . . . .
C23 C 0.4588(4) 0.5117(3) 0.6950(3) 0.0250(6) Uani 1 1 d . . . . .
H23 H 0.5080 0.4404 0.7494 0.030 Uiso 1 1 calc R . . . .
C5 C 0.1669(4) 0.3746(4) 0.3216(3) 0.0332(8) Uani 1 1 d . . . . .
H5A H 0.2295 0.4504 0.3192 0.050 Uiso 1 1 calc GR . . . .
H5B H 0.0943 0.3577 0.2315 0.050 Uiso 1 1 calc GR . . . .
H5C H 0.2329 0.2987 0.3530 0.050 Uiso 1 1 calc GR . . . .
C14 C 0.3418(3) 0.3859(3) 1.0126(3) 0.0236(6) Uani 1 1 d . . . . .
H14 H 0.2834 0.3119 0.9722 0.028 Uiso 1 1 calc R . . . .
C13 C -0.0028(4) 0.5491(3) 0.9048(3) 0.0261(6) Uani 1 1 d . . . . .
H13 H 0.0606 0.6222 0.9091 0.031 Uiso 1 1 calc R . . . .
C20 C 0.3113(4) 0.7240(3) 0.5316(3) 0.0276(7) Uani 1 1 d . . . . .
H20 H 0.2612 0.7944 0.4763 0.033 Uiso 1 1 calc R . . . .
C7 C 0.3417(3) 0.4971(3) 0.9340(3) 0.0207(6) Uani 1 1 d . . . . .
C12 C -0.1057(4) 0.5489(4) 0.9772(3) 0.0320(7) Uani 1 1 d . . . . .
H12 H -0.1106 0.6224 1.0295 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.222(4) . ?
N2 C1 1.382(4) . ?
N2 C6 1.450(4) . ?
N2 C7 1.433(3) . ?
N1 C1 1.286(4) . ?
N1 C2 1.422(4) . ?
C8 C1 1.500(4) . ?
C8 C9 1.394(4) . ?
C8 C13 1.385(4) . ?
C6 C19 1.380(4) . ?
C6 C23 1.393(4) . ?
N3 C2 1.357(4) . ?
N3 C4 1.444(4) . ?
N3 C5 1.459(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.391(4) . ?
C17 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.393(5) . ?
C15 C14 1.396(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(5) . ?
C21 C20 1.379(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C22 H22 0.9300 . ?
C22 C23 1.395(4) . ?
C18 H18 0.9300 . ?
C18 C7 1.392(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.379(5) . ?
C11 C12 1.384(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.397(4) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C23 H23 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C7 1.390(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.397(4) . ?
C20 H20 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N2 C6 120.3(2) . . ?
C1 N2 C7 121.9(2) . . ?
C7 N2 C6 117.5(2) . . ?
C1 N1 C2 121.9(3) . . ?
C9 C8 C1 118.6(3) . . ?
C13 C8 C1 122.2(3) . . ?
C13 C8 C9 119.1(3) . . ?
N2 C1 C8 117.7(2) . . ?
N1 C1 N2 126.7(3) . . ?
N1 C1 C8 115.5(3) . . ?
C19 C6 N2 119.4(3) . . ?
C19 C6 C23 120.8(3) . . ?
C23 C6 N2 119.7(3) . . ?
C2 N3 C4 124.2(3) . . ?
C2 N3 C5 118.4(3) . . ?
C4 N3 C5 116.6(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.3(3) . . ?
O1 C2 N1 121.5(3) . . ?
O1 C2 N3 124.6(3) . . ?
N3 C2 N1 113.5(3) . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C22 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C7 120.5(3) . . ?
C7 C18 H18 119.8 . . ?
C10 C11 H11 120.3 . . ?
C10 C11 C12 119.3(3) . . ?
C12 C11 H11 120.3 . . ?
C6 C19 H19 120.3 . . ?
C6 C19 C20 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C6 C23 C22 119.1(3) . . ?
C6 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C15 C14 H14 119.9 . . ?
C7 C14 C15 120.3(3) . . ?
C7 C14 H14 119.9 . . ?
C8 C13 H13 120.1 . . ?
C8 C13 C12 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C18 C7 N2 120.4(3) . . ?
C14 C7 N2 120.5(3) . . ?
C14 C7 C18 119.2(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?

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
N2 C6 C19 C20 179.2(3) . . . . ?
N2 C6 C23 C22 -178.4(3) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C8 C13 C12 C11 0.2(5) . . . . ?
C1 N2 C6 C19 64.4(4) . . . . ?
C1 N2 C6 C23 -117.4(3) . . . . ?
C1 N2 C7 C18 -145.5(3) . . . . ?
C1 N2 C7 C14 34.4(4) . . . . ?
C1 N1 C2 O1 61.9(4) . . . . ?
C1 N1 C2 N3 -125.4(3) . . . . ?
C1 C8 C9 C10 -177.2(3) . . . . ?
C1 C8 C13 C12 176.8(3) . . . . ?
C6 N2 C1 N1 27.1(5) . . . . ?
C6 N2 C1 C8 -149.0(3) . . . . ?
C6 N2 C7 C18 40.6(4) . . . . ?
C6 N2 C7 C14 -139.5(3) . . . . ?
C6 C19 C20 C21 -1.1(5) . . . . ?
C17 C18 C7 N2 179.4(3) . . . . ?
C17 C18 C7 C14 -0.4(4) . . . . ?
C2 N1 C1 N2 16.0(5) . . . . ?
C2 N1 C1 C8 -167.9(3) . . . . ?
C15 C14 C7 N2 -178.6(3) . . . . ?
C15 C14 C7 C18 1.3(4) . . . . ?
C21 C22 C23 C6 -0.4(5) . . . . ?
C9 C8 C1 N2 -147.1(3) . . . . ?
C9 C8 C1 N1 36.4(4) . . . . ?
C9 C8 C13 C12 0.1(4) . . . . ?
C4 N3 C2 O1 -177.3(3) . . . . ?
C4 N3 C2 N1 10.3(4) . . . . ?
C22 C21 C20 C19 0.5(5) . . . . ?
C18 C17 C16 C15 1.0(5) . . . . ?
C19 C6 C23 C22 -0.2(5) . . . . ?
C10 C11 C12 C13 -0.1(5) . . . . ?
C16 C17 C18 C7 -0.7(5) . . . . ?
C16 C15 C14 C7 -1.1(5) . . . . ?
C23 C6 C19 C20 1.0(5) . . . . ?
C5 N3 C2 O1 -8.2(5) . . . . ?
C5 N3 C2 N1 179.4(3) . . . . ?
C14 C15 C16 C17 -0.1(5) . . . . ?
C13 C8 C1 N2 36.2(4) . . . . ?
C13 C8 C1 N1 -140.3(3) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C7 N2 C1 N1 -146.7(3) . . . . ?
C7 N2 C1 C8 37.2(4) . . . . ?
C7 N2 C6 C19 -121.5(3) . . . . ?
C7 N2 C6 C23 56.7(4) . . . . ?
C12 C11 C10 C9 -0.2(5) . . . . ?

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C17(H17), C15(H15), C21(H21), C9(H9), C22(H22), C18(H18), C11(H11), C19(H19),
 C10(H10), C16(H16), C23(H23), C14(H14), C13(H13), C20(H20), C12(H12)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2014/6
####################################################################### 
# 
# 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_3aa
_database_code_depnum_ccdc_archive 'CCDC 1410193'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H19 N3 O'
_chemical_formula_sum            'C17 H19 N3 O'
_chemical_formula_weight         281.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5535(3)
_cell_length_b                   6.1044(3)
_cell_length_c                   26.1423(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.150(3)
_cell_angle_gamma                90
_cell_volume                     1512.74(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5745
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.7450
_cell_measurement_theta_min      3.1290
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            23114
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.815
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00   19.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  2 omega  -89.00  -56.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  178.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   22.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -99.0000    0.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega   -3.00   43.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega  -48.00   -8.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   85.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  178.0000   60.0000 47

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   38.0000 -150.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega  -46.00   40.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -57.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
  9 omega  -92.00  -21.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  152.0000  102.0000 71

#__ type_ start__ end____ width___ exp.time_
 10 omega  -22.00    5.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega  -73.00  -30.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  121.0000  -57.0000 43

#__ type_ start__ end____ width___ exp.time_
 12 omega  -89.00  -58.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.8777  -38.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 13 omega   -3.00   83.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000  -60.0000 86

#__ type_ start__ end____ width___ exp.time_
 14 omega   -3.00   88.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152   57.0000   60.0000 91

#__ type_ start__ end____ width___ exp.time_
 15 omega  -52.00  -27.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8152  -38.0000  120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0258359000
_diffrn_orient_matrix_UB_12      0.1081473000
_diffrn_orient_matrix_UB_13      0.0044747000
_diffrn_orient_matrix_UB_21      -0.0022494000
_diffrn_orient_matrix_UB_22      -0.0137736000
_diffrn_orient_matrix_UB_23      0.0268166000
_diffrn_orient_matrix_UB_31      0.0702123000
_diffrn_orient_matrix_UB_32      -0.0402145000
_diffrn_orient_matrix_UB_33      0.0028467000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2657
_reflns_number_total             3439
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3439
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+0.4110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1158
_refine_ls_wR_factor_ref         0.1247
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.28470(12) 0.75350(19) 0.02688(4) 0.0485(3) Uani 1 1 d . . . . .
N1 N 0.27989(13) 0.4343(2) 0.07096(4) 0.0406(3) Uani 1 1 d . . . . .
N2 N 0.37969(13) 0.7893(2) 0.07480(5) 0.0430(3) Uani 1 1 d . . . . .
N3 N 0.17917(15) 0.4570(3) -0.01574(5) 0.0558(4) Uani 1 1 d . . . . .
C1 C 0.33395(14) 0.6062(2) 0.10741(5) 0.0366(3) Uani 1 1 d . . . . .
C2 C 0.24813(15) 0.5356(3) 0.02827(5) 0.0419(4) Uani 1 1 d . . . . .
C3 C 0.51549(17) 0.3237(3) 0.14205(7) 0.0544(4) Uani 1 1 d . . . . .
H3 H 0.4807 0.2296 0.1155 0.065 Uiso 1 1 calc R . . . .
C4 C 0.1552(2) 0.5848(4) -0.06261(7) 0.0734(6) Uani 1 1 d . . . . .
H4A H 0.1930 0.5085 -0.0899 0.110 Uiso 1 1 calc GR . . . .
H4B H 0.2010 0.7244 -0.0572 0.110 Uiso 1 1 calc GR . . . .
H4C H 0.0557 0.6065 -0.0718 0.110 Uiso 1 1 calc GR . . . .
C5 C 0.1280(2) 0.2341(3) -0.01679(8) 0.0664(5) Uani 1 1 d . . . . .
H5A H 0.1588 0.1646 0.0156 0.100 Uiso 1 1 calc GR . . . .
H5B H 0.1644 0.1552 -0.0440 0.100 Uiso 1 1 calc GR . . . .
H5C H 0.0268 0.2343 -0.0226 0.100 Uiso 1 1 calc GR . . . .
C6 C 0.45589(15) 0.5277(3) 0.14610(5) 0.0406(3) Uani 1 1 d . . . . .
C7 C 0.21141(14) 0.6866(2) 0.13514(5) 0.0374(3) Uani 1 1 d . . . . .
C8 C 0.62785(19) 0.2592(4) 0.17784(9) 0.0702(6) Uani 1 1 d . . . . .
H9 H 0.6682 0.1218 0.1750 0.084 Uiso 1 1 calc R . . . .
C9 C 0.67977(19) 0.3955(4) 0.21728(8) 0.0742(7) Uani 1 1 d . . . . .
H10 H 0.7554 0.3514 0.2409 0.089 Uiso 1 1 calc R . . . .
C10 C 0.52134(18) 0.7597(3) 0.05943(7) 0.0594(5) Uani 1 1 d . . . . .
H8A H 0.5909 0.7845 0.0886 0.089 Uiso 1 1 calc GR . . . .
H8B H 0.5351 0.8622 0.0327 0.089 Uiso 1 1 calc GR . . . .
H8C H 0.5305 0.6132 0.0470 0.089 Uiso 1 1 calc GR . . . .
C11 C 0.61982(19) 0.5972(4) 0.22177(7) 0.0700(6) Uani 1 1 d . . . . .
H11 H 0.6545 0.6897 0.2487 0.084 Uiso 1 1 calc R . . . .
C12 C 0.50781(17) 0.6642(3) 0.18646(6) 0.0542(4) Uani 1 1 d . . . . .
H12 H 0.4673 0.8012 0.1898 0.065 Uiso 1 1 calc R . . . .
C13 C 0.14857(16) 0.5361(3) 0.16503(6) 0.0465(4) Uani 1 1 d . . . . .
H13 H 0.1858 0.3956 0.1694 0.056 Uiso 1 1 calc R . . . .
C14 C 0.03139(17) 0.5925(3) 0.18832(6) 0.0556(5) Uani 1 1 d . . . . .
H14 H -0.0100 0.4900 0.2081 0.067 Uiso 1 1 calc R . . . .
C15 C -0.02401(18) 0.8007(3) 0.18226(7) 0.0571(5) Uani 1 1 d . . . . .
H15 H -0.1036 0.8387 0.1975 0.069 Uiso 1 1 calc R . . . .
C16 C 0.03892(18) 0.9515(3) 0.15363(7) 0.0557(4) Uani 1 1 d . . . . .
H16 H 0.0021 1.0924 0.1499 0.067 Uiso 1 1 calc R . . . .
C17 C 0.15686(16) 0.8968(3) 0.13019(6) 0.0452(4) Uani 1 1 d . . . . .
H17 H 0.1991 1.0011 0.1112 0.054 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.4688(16) . ?
O1 C2 1.3768(19) . ?
N1 C1 1.4677(18) . ?
N1 C2 1.2790(18) . ?
N2 C1 1.5030(19) . ?
N2 C10 1.470(2) . ?
N3 C2 1.3416(19) . ?
N3 C4 1.447(2) . ?
N3 C5 1.445(2) . ?
C1 C6 1.5220(19) . ?
C1 C7 1.532(2) . ?
C3 H3 0.9300 . ?
C3 C6 1.379(2) . ?
C3 C8 1.390(2) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C12 1.387(2) . ?
C7 C13 1.390(2) . ?
C7 C17 1.385(2) . ?
C8 H9 0.9300 . ?
C8 C9 1.369(3) . ?
C9 H10 0.9300 . ?
C9 C11 1.369(3) . ?
C10 H8A 0.9600 . ?
C10 H8B 0.9600 . ?
C10 H8C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.385(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.383(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 N2 104.65(10) . . ?
C2 N1 C1 104.29(12) . . ?
O1 N2 C1 100.42(10) . . ?
O1 N2 C10 103.93(12) . . ?
C10 N2 C1 113.98(12) . . ?
C2 N3 C4 122.84(17) . . ?
C2 N3 C5 118.82(15) . . ?
C5 N3 C4 118.33(15) . . ?
N1 C1 N2 105.48(11) . . ?
N1 C1 C6 112.62(12) . . ?
N1 C1 C7 107.96(11) . . ?
N2 C1 C6 111.01(11) . . ?
N2 C1 C7 108.87(12) . . ?
C6 C1 C7 110.68(11) . . ?
N1 C2 O1 117.18(13) . . ?
N1 C2 N3 127.82(16) . . ?
N3 C2 O1 114.97(13) . . ?
C6 C3 H3 120.1 . . ?
C6 C3 C8 119.71(18) . . ?
C8 C3 H3 120.1 . . ?
N3 C4 H4A 109.5 . . ?
N3 C4 H4B 109.5 . . ?
N3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N3 C5 H5A 109.5 . . ?
N3 C5 H5B 109.5 . . ?
N3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 C1 121.50(14) . . ?
C3 C6 C12 119.28(15) . . ?
C12 C6 C1 119.21(14) . . ?
C13 C7 C1 117.58(13) . . ?
C17 C7 C1 123.60(13) . . ?
C17 C7 C13 118.76(14) . . ?
C3 C8 H9 119.6 . . ?
C9 C8 C3 120.8(2) . . ?
C9 C8 H9 119.6 . . ?
C8 C9 H10 120.2 . . ?
C11 C9 C8 119.68(17) . . ?
C11 C9 H10 120.2 . . ?
N2 C10 H8A 109.5 . . ?
N2 C10 H8B 109.5 . . ?
N2 C10 H8C 109.5 . . ?
H8A C10 H8B 109.5 . . ?
H8A C10 H8C 109.5 . . ?
H8B C10 H8C 109.5 . . ?
C9 C11 H11 119.8 . . ?
C9 C11 C12 120.34(19) . . ?
C12 C11 H11 119.8 . . ?
C6 C12 H12 119.9 . . ?
C11 C12 C6 120.20(19) . . ?
C11 C12 H12 119.9 . . ?
C7 C13 H13 119.6 . . ?
C14 C13 C7 120.85(16) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.96(17) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.57(16) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 119.5 . . ?
C15 C16 C17 120.94(17) . . ?
C17 C16 H16 119.5 . . ?
C7 C17 C16 119.89(16) . . ?
C7 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?

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
O1 N2 C1 N1 27.79(13) . . . . ?
O1 N2 C1 C6 150.06(11) . . . . ?
O1 N2 C1 C7 -87.86(12) . . . . ?
N1 C1 C6 C3 6.79(19) . . . . ?
N1 C1 C6 C12 -172.96(13) . . . . ?
N1 C1 C7 C13 62.28(16) . . . . ?
N1 C1 C7 C17 -114.88(14) . . . . ?
N2 O1 C2 N1 11.90(16) . . . . ?
N2 O1 C2 N3 -169.81(12) . . . . ?
N2 C1 C6 C3 -111.24(16) . . . . ?
N2 C1 C6 C12 69.02(17) . . . . ?
N2 C1 C7 C13 176.32(12) . . . . ?
N2 C1 C7 C17 -0.84(18) . . . . ?
C1 N1 C2 O1 6.56(17) . . . . ?
C1 N1 C2 N3 -171.48(15) . . . . ?
C1 C6 C12 C11 -179.22(15) . . . . ?
C1 C7 C13 C14 -175.54(13) . . . . ?
C1 C7 C17 C16 175.22(14) . . . . ?
C2 O1 N2 C1 -23.66(13) . . . . ?
C2 O1 N2 C10 94.47(13) . . . . ?
C2 N1 C1 N2 -21.95(14) . . . . ?
C2 N1 C1 C6 -143.18(13) . . . . ?
C2 N1 C1 C7 94.32(13) . . . . ?
C3 C6 C12 C11 1.0(2) . . . . ?
C3 C8 C9 C11 0.4(3) . . . . ?
C4 N3 C2 O1 5.1(2) . . . . ?
C4 N3 C2 N1 -176.86(16) . . . . ?
C5 N3 C2 O1 -175.77(14) . . . . ?
C5 N3 C2 N1 2.3(2) . . . . ?
C6 C1 C7 C13 -61.40(16) . . . . ?
C6 C1 C7 C17 121.45(15) . . . . ?
C6 C3 C8 C9 0.3(3) . . . . ?
C7 C1 C6 C3 127.74(15) . . . . ?
C7 C1 C6 C12 -52.00(18) . . . . ?
C7 C13 C14 C15 -0.4(2) . . . . ?
C8 C3 C6 C1 179.23(15) . . . . ?
C8 C3 C6 C12 -1.0(2) . . . . ?
C8 C9 C11 C12 -0.4(3) . . . . ?
C9 C11 C12 C6 -0.3(3) . . . . ?
C10 N2 C1 N1 -82.68(15) . . . . ?
C10 N2 C1 C6 39.59(17) . . . . ?
C10 N2 C1 C7 161.67(13) . . . . ?
C13 C7 C17 C16 -1.9(2) . . . . ?
C13 C14 C15 C16 -0.8(2) . . . . ?
C14 C15 C16 C17 0.7(3) . . . . ?
C15 C16 C17 C7 0.7(2) . . . . ?
C17 C7 C13 C14 1.8(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_4ec
_database_code_depnum_ccdc_archive 'CCDC 1410194'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.28 svn.r2899 for OlexSys, GUI svn.r4781)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H25 N3 O'
_chemical_formula_sum            'C32 H25 N3 O'
_chemical_formula_weight         467.55
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H25 N3 O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   17.0999(2)
_cell_length_b                   8.90736(10)
_cell_length_c                   15.9119(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2423.63(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.9870
_cell_measurement_theta_min      5.5980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.613
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent white'
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17036
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.449
_diffrn_reflns_theta_min         5.173
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0146964000
_diffrn_orient_matrix_UB_12      0.0133625000
_diffrn_orient_matrix_UB_13      0.0952454000
_diffrn_orient_matrix_UB_21      0.0698604000
_diffrn_orient_matrix_UB_22      -0.1048865000
_diffrn_orient_matrix_UB_23      0.0170519000
_diffrn_orient_matrix_UB_31      0.0549171000
_diffrn_orient_matrix_UB_32      0.1368963000
_diffrn_orient_matrix_UB_33      0.0037164000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.927
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4649
_reflns_number_total             4736
_reflns_odcompleteness_completeness 94.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    ?
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0274
_refine_ls_R_factor_gt           0.0268
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.3771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31),
 C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.01029(9) 0.18059(18) 0.58047(10) 0.0160(3) Uani 1 1 d . . . . .
C2 C 0.10130(9) 0.05204(17) 0.53135(11) 0.0162(3) Uani 1 1 d . . . . .
C4 C 0.05079(9) 0.09016(19) 0.38616(10) 0.0180(3) Uani 1 1 d . . . . .
C5 C 0.19119(10) 0.06039(19) 0.41368(10) 0.0175(3) Uani 1 1 d . . . . .
C6 C -0.11717(9) 0.27204(18) 0.66949(11) 0.0169(3) Uani 1 1 d . . . . .
C7 C -0.12805(9) 0.03105(18) 0.59556(11) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.02517(10) 0.33430(18) 0.57785(11) 0.0175(3) Uani 1 1 d . . . . .
C9 C 0.10102(10) 0.3583(2) 0.60733(11) 0.0206(3) Uani 1 1 d . . . . .
H9 H 0.1295 0.2790 0.6299 0.025 Uiso 1 1 calc R . . . .
C10 C 0.13413(10) 0.5010(2) 0.60287(12) 0.0248(4) Uani 1 1 d . . . . .
H10 H 0.1849 0.5165 0.6220 0.030 Uiso 1 1 calc R . . . .
C11 C 0.09172(11) 0.6201(2) 0.57011(13) 0.0262(4) Uani 1 1 d . . . . .
H11 H 0.1141 0.7151 0.5669 0.031 Uiso 1 1 calc R . . . .
C12 C 0.01575(11) 0.5971(2) 0.54214(12) 0.0257(4) Uani 1 1 d . . . . .
H12 H -0.0130 0.6773 0.5211 0.031 Uiso 1 1 calc R . . . .
C13 C -0.01754(10) 0.4549(2) 0.54542(12) 0.0213(3) Uani 1 1 d . . . . .
H13 H -0.0683 0.4401 0.5260 0.026 Uiso 1 1 calc R . . . .
C14 C -0.14265(10) -0.05731(19) 0.66539(12) 0.0210(3) Uani 1 1 d . . . . .
H14 H -0.1278 -0.0244 0.7185 0.025 Uiso 1 1 calc R . . . .
C15 C -0.17961(11) -0.1956(2) 0.65578(13) 0.0261(4) Uani 1 1 d . . . . .
H15 H -0.1898 -0.2547 0.7027 0.031 Uiso 1 1 calc R . . . .
C16 C -0.20143(10) -0.24596(19) 0.57649(14) 0.0248(4) Uani 1 1 d . . . . .
H16 H -0.2254 -0.3389 0.5701 0.030 Uiso 1 1 calc R . . . .
C17 C -0.18695(11) -0.1557(2) 0.50690(13) 0.0258(4) Uani 1 1 d . . . . .
H17 H -0.2016 -0.1883 0.4537 0.031 Uiso 1 1 calc R . . . .
C18 C -0.15061(10) -0.0169(2) 0.51643(12) 0.0214(4) Uani 1 1 d . . . . .
H18 H -0.1415 0.0435 0.4698 0.026 Uiso 1 1 calc R . . . .
C19 C -0.07198(9) 0.30701(18) 0.73957(11) 0.0192(3) Uani 1 1 d . . . . .
H19 H -0.0215 0.2692 0.7444 0.023 Uiso 1 1 calc R . . . .
C20 C -0.10240(10) 0.39867(19) 0.80244(12) 0.0219(3) Uani 1 1 d . . . . .
H20 H -0.0721 0.4226 0.8491 0.026 Uiso 1 1 calc R . . . .
C21 C -0.17812(11) 0.45455(19) 0.79553(12) 0.0231(4) Uani 1 1 d . . . . .
H21 H -0.1989 0.5142 0.8380 0.028 Uiso 1 1 calc R . . . .
C22 C -0.22261(10) 0.42095(19) 0.72501(13) 0.0223(3) Uani 1 1 d . . . . .
H22 H -0.2729 0.4597 0.7199 0.027 Uiso 1 1 calc R . . . .
C23 C -0.19258(10) 0.33004(18) 0.66209(11) 0.0193(3) Uani 1 1 d . . . . .
H23 H -0.2227 0.3078 0.6150 0.023 Uiso 1 1 calc R . . . .
C24 C -0.00312(10) -0.0241(2) 0.37326(12) 0.0218(3) Uani 1 1 d . . . . .
H24 H -0.0025 -0.1096 0.4068 0.026 Uiso 1 1 calc R . . . .
C25 C -0.05818(10) -0.0089(2) 0.30925(13) 0.0254(4) Uani 1 1 d . . . . .
H25 H -0.0950 -0.0843 0.3008 0.030 Uiso 1 1 calc R . . . .
C26 C -0.05890(10) 0.1168(2) 0.25803(11) 0.0254(4) Uani 1 1 d . . . . .
H26 H -0.0952 0.1249 0.2147 0.031 Uiso 1 1 calc R . . . .
C27 C -0.00497(11) 0.2306(2) 0.27198(12) 0.0247(4) Uani 1 1 d . . . . .
H27 H -0.0052 0.3155 0.2380 0.030 Uiso 1 1 calc R . . . .
C28 C 0.04929(10) 0.2182(2) 0.33642(11) 0.0213(3) Uani 1 1 d . . . . .
H28 H 0.0846 0.2956 0.3463 0.026 Uiso 1 1 calc R . . . .
C29 C 0.21002(10) -0.0633(2) 0.36459(11) 0.0205(3) Uani 1 1 d . . . . .
H29 H 0.1730 -0.1378 0.3550 0.025 Uiso 1 1 calc R . . . .
C30 C 0.28431(11) -0.0754(2) 0.32980(12) 0.0232(4) Uani 1 1 d . . . . .
H30 H 0.2969 -0.1580 0.2967 0.028 Uiso 1 1 calc R . . . .
C31 C 0.33969(10) 0.0350(2) 0.34432(12) 0.0240(4) Uani 1 1 d . . . . .
H31 H 0.3893 0.0270 0.3208 0.029 Uiso 1 1 calc R . . . .
C32 C 0.32071(11) 0.1579(2) 0.39420(12) 0.0256(4) Uani 1 1 d . . . . .
H32 H 0.3580 0.2316 0.4046 0.031 Uiso 1 1 calc R . . . .
C33 C 0.24644(10) 0.1715(2) 0.42866(11) 0.0220(4) Uani 1 1 d . . . . .
H33 H 0.2338 0.2543 0.4615 0.026 Uiso 1 1 calc R . . . .
N1 N 0.02417(8) 0.05850(15) 0.55883(9) 0.0167(3) Uani 1 1 d . . . . .
N2 N -0.08818(8) 0.17331(15) 0.60523(9) 0.0169(3) Uani 1 1 d . . . . .
N3 N 0.11277(8) 0.07386(16) 0.44663(9) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.15516(7) 0.01786(13) 0.57801(8) 0.0197(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.498(2) . ?
C1 N1 1.284(2) . ?
C1 N2 1.390(2) . ?
C2 N1 1.391(2) . ?
C2 N3 1.376(2) . ?
C2 O1 1.222(2) . ?
C4 C24 1.389(2) . ?
C4 C28 1.388(3) . ?
C4 N3 1.439(2) . ?
C5 C29 1.388(2) . ?
C5 C33 1.389(2) . ?
C5 N3 1.445(2) . ?
C6 C19 1.392(2) . ?
C6 C23 1.394(2) . ?
C6 N2 1.437(2) . ?
C7 C14 1.384(2) . ?
C7 C18 1.384(2) . ?
C7 N2 1.447(2) . ?
C8 C9 1.396(2) . ?
C8 C13 1.398(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.393(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.392(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.391(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.393(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.385(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.388(3) . ?
C27 H27 0.9300 . ?
C27 C28 1.387(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.390(3) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.391(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C8 125.52(14) . . ?
N1 C1 N2 118.43(14) . . ?
N2 C1 C8 116.00(14) . . ?
N3 C2 N1 115.94(14) . . ?
O1 C2 N1 122.29(15) . . ?
O1 C2 N3 121.54(15) . . ?
C24 C4 N3 120.93(16) . . ?
C28 C4 C24 120.37(16) . . ?
C28 C4 N3 118.53(15) . . ?
C29 C5 C33 120.27(16) . . ?
C29 C5 N3 119.03(15) . . ?
C33 C5 N3 120.66(15) . . ?
C19 C6 C23 119.87(16) . . ?
C19 C6 N2 121.03(15) . . ?
C23 C6 N2 119.07(15) . . ?
C14 C7 N2 119.83(15) . . ?
C18 C7 C14 120.30(15) . . ?
C18 C7 N2 119.86(15) . . ?
C9 C8 C1 120.45(15) . . ?
C9 C8 C13 119.46(15) . . ?
C13 C8 C1 120.09(15) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.01(16) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.30(16) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.78(17) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.42(18) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 120.0 . . ?
C12 C13 C8 120.01(16) . . ?
C12 C13 H13 120.0 . . ?
C7 C14 H14 120.1 . . ?
C7 C14 C15 119.77(17) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.44(17) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.25(16) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C18 120.41(18) . . ?
C18 C17 H17 119.8 . . ?
C7 C18 C17 119.82(17) . . ?
C7 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C6 C19 H19 120.0 . . ?
C6 C19 C20 119.97(15) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.05(17) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.77(17) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.44(16) . . ?
C23 C22 H22 119.8 . . ?
C6 C23 H23 120.1 . . ?
C22 C23 C6 119.88(17) . . ?
C22 C23 H23 120.1 . . ?
C4 C24 H24 120.5 . . ?
C4 C24 C25 119.04(17) . . ?
C25 C24 H24 120.5 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 120.96(17) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.37(17) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.28(18) . . ?
C28 C27 H27 119.9 . . ?
C4 C28 H28 120.0 . . ?
C27 C28 C4 119.94(17) . . ?
C27 C28 H28 120.0 . . ?
C5 C29 H29 120.1 . . ?
C5 C29 C30 119.87(16) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.9 . . ?
C31 C30 C29 120.20(17) . . ?
C31 C30 H30 119.9 . . ?
C30 C31 H31 120.2 . . ?
C30 C31 C32 119.65(17) . . ?
C32 C31 H31 120.2 . . ?
C31 C32 H32 119.8 . . ?
C33 C32 C31 120.50(17) . . ?
C33 C32 H32 119.8 . . ?
C5 C33 H33 120.2 . . ?
C32 C33 C5 119.50(16) . . ?
C32 C33 H33 120.2 . . ?
C1 N1 C2 123.68(14) . . ?
C1 N2 C6 120.24(14) . . ?
C1 N2 C7 117.52(13) . . ?
C6 N2 C7 116.68(13) . . ?
C2 N3 C4 124.35(14) . . ?
C2 N3 C5 118.43(14) . . ?
C4 N3 C5 116.71(14) . . ?

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
C1 C8 C9 C10 178.55(16) . . . . ?
C1 C8 C13 C12 -179.26(17) . . . . ?
C4 C24 C25 C26 1.0(3) . . . . ?
C5 C29 C30 C31 0.3(3) . . . . ?
C6 C19 C20 C21 0.4(3) . . . . ?
C7 C14 C15 C16 0.5(3) . . . . ?
C8 C1 N1 C2 1.6(3) . . . . ?
C8 C1 N2 C6 -36.9(2) . . . . ?
C8 C1 N2 C7 170.22(14) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C8 C13 C12 0.5(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C13 -1.1(3) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C13 C8 C9 C10 -1.2(3) . . . . ?
C14 C7 C18 C17 -1.1(3) . . . . ?
C14 C7 N2 C1 104.83(18) . . . . ?
C14 C7 N2 C6 -49.0(2) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C7 0.6(3) . . . . ?
C18 C7 C14 C15 0.6(2) . . . . ?
C18 C7 N2 C1 -74.4(2) . . . . ?
C18 C7 N2 C6 131.76(16) . . . . ?
C19 C6 C23 C22 -0.7(2) . . . . ?
C19 C6 N2 C1 -39.1(2) . . . . ?
C19 C6 N2 C7 113.98(17) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C22 C23 C6 -0.1(2) . . . . ?
C23 C6 C19 C20 0.6(2) . . . . ?
C23 C6 N2 C1 142.63(15) . . . . ?
C23 C6 N2 C7 -64.3(2) . . . . ?
C24 C4 C28 C27 -1.7(3) . . . . ?
C24 C4 N3 C2 -61.0(2) . . . . ?
C24 C4 N3 C5 110.68(18) . . . . ?
C24 C25 C26 C27 -1.4(3) . . . . ?
C25 C26 C27 C28 0.2(3) . . . . ?
C26 C27 C28 C4 1.3(3) . . . . ?
C28 C4 C24 C25 0.6(3) . . . . ?
C28 C4 N3 C2 123.69(18) . . . . ?
C28 C4 N3 C5 -64.6(2) . . . . ?
C29 C5 C33 C32 0.0(3) . . . . ?
C29 C5 N3 C2 108.29(18) . . . . ?
C29 C5 N3 C4 -63.9(2) . . . . ?
C29 C30 C31 C32 0.3(3) . . . . ?
C30 C31 C32 C33 -0.8(3) . . . . ?
C31 C32 C33 C5 0.6(3) . . . . ?
C33 C5 C29 C30 -0.4(3) . . . . ?
C33 C5 N3 C2 -73.6(2) . . . . ?
C33 C5 N3 C4 114.18(18) . . . . ?
N1 C1 C8 C9 -44.4(3) . . . . ?
N1 C1 C8 C13 135.30(18) . . . . ?
N1 C1 N2 C6 145.73(15) . . . . ?
N1 C1 N2 C7 -7.1(2) . . . . ?
N1 C2 N3 C4 -5.2(2) . . . . ?
N1 C2 N3 C5 -176.72(14) . . . . ?
N2 C1 C8 C9 138.46(16) . . . . ?
N2 C1 C8 C13 -41.8(2) . . . . ?
N2 C1 N1 C2 178.65(15) . . . . ?
N2 C6 C19 C20 -177.72(15) . . . . ?
N2 C6 C23 C22 177.59(15) . . . . ?
N2 C7 C14 C15 -178.70(15) . . . . ?
N2 C7 C18 C17 178.15(15) . . . . ?
N3 C2 N1 C1 -87.4(2) . . . . ?
N3 C4 C24 C25 -174.66(16) . . . . ?
N3 C4 C28 C27 173.64(16) . . . . ?
N3 C5 C29 C30 177.66(16) . . . . ?
N3 C5 C33 C32 -178.11(16) . . . . ?
O1 C2 N1 C1 98.0(2) . . . . ?
O1 C2 N3 C4 169.49(15) . . . . ?
O1 C2 N3 C5 -2.1(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_6ed
_database_code_depnum_ccdc_archive 'CCDC 1410195'
_audit_update_record             
;
2015-07-01 deposited with the CCDC.
2015-09-09 downloaded from the CCDC.
;
_audit_creation_date             2014-09-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.08.28 svn.r2986 for OlexSys, GUI svn.r4874)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C32 H24 Br N3 O'
_chemical_formula_sum            'C32 H24 Br N3 O'
_chemical_formula_weight         546.45
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.5963(6)
_cell_length_b                   10.8613(5)
_cell_length_c                   13.9872(6)
_cell_angle_alpha                83.343(4)
_cell_angle_beta                 69.786(5)
_cell_angle_gamma                61.160(5)
_cell_volume                     1320.74(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    16732
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      4.6270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.350
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69498
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31953
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.494
_diffrn_reflns_theta_min         3.374
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 10.3829
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -87.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   19.0000   60.0000 127

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   22.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000   90.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -37.00   26.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  -60.0000 63

#__ type_ start__ end____ width___ exp.time_
  4 omega   72.00  129.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787 -178.0000  120.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  6 omega   64.00  124.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   97.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000 -141.5526 49

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00   76.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000 -141.5526 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   55.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000   -5.9403 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   90.00  128.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -177.0453 38

#__ type_ start__ end____ width___ exp.time_
 11 omega  109.00  141.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 12 omega   89.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000 -120.0000 59

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   92.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -20.0000 -177.0453 26

#__ type_ start__ end____ width___ exp.time_
 16 omega   70.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -66.0000   28.6581 30

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   90.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00   96.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000 -120.0000 57

#__ type_ start__ end____ width___ exp.time_
 19 omega   59.00   85.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   31.00  173.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000  -60.0000 142

#__ type_ start__ end____ width___ exp.time_
 21 omega   38.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
 23 omega  120.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   -8.0000   99.5787 40

#__ type_ start__ end____ width___ exp.time_
 24 omega   88.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega   83.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega   36.00   79.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  120.0000 43

#__ type_ start__ end____ width___ exp.time_
 27 omega   93.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega  142.00  175.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
 29 omega   95.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 30 omega   43.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000   60.0000 55

#__ type_ start__ end____ width___ exp.time_
 31 omega   88.00  115.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
 32 omega   43.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 33 omega  124.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  120.0000 36

#__ type_ start__ end____ width___ exp.time_
 34 omega   83.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 35 omega   36.00  108.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   -8.0000   99.5787 72

#__ type_ start__ end____ width___ exp.time_
 36 omega   72.00   97.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 37 omega  103.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -80.0000   -5.9403 26

#__ type_ start__ end____ width___ exp.time_
 38 omega  104.00  129.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 39 omega   99.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -72.0000  135.1193 47

#__ type_ start__ end____ width___ exp.time_
 40 omega   48.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 66

#__ type_ start__ end____ width___ exp.time_
 41 omega   95.00  120.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  178.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega  125.00  150.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 43 omega   40.00   66.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 44 omega   89.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -77.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 45 omega   58.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -121.0000  -65.7468 61

#__ type_ start__ end____ width___ exp.time_
 46 omega  -99.00  -73.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -73.0000  -91.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega  -40.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 29

#__ type_ start__ end____ width___ exp.time_
 48 omega -112.00  -55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
 49 omega  -58.00  -10.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -73.0000  -91.0000 48

#__ type_ start__ end____ width___ exp.time_
 50 omega   21.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787   38.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
 51 omega    6.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       44.0000   89.0000   80.2486 25

#__ type_ start__ end____ width___ exp.time_
 52 omega   17.00   42.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000 -123.4900 25

#__ type_ start__ end____ width___ exp.time_
 53 omega   18.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   79.0000  -15.0215 25

#__ type_ start__ end____ width___ exp.time_
 54 omega   18.00   44.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   80.0000   36.2881 26

#__ type_ start__ end____ width___ exp.time_
 55 omega   17.00   43.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       52.0000   81.0000  -71.9030 26

#__ type_ start__ end____ width___ exp.time_
 56 omega   22.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   78.0000  143.7452 25

#__ type_ start__ end____ width___ exp.time_
 57 omega   29.00   55.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       60.0000   77.0000  168.0786 26

#__ type_ start__ end____ width___ exp.time_
 58 omega   32.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000  -83.2688 75

#__ type_ start__ end____ width___ exp.time_
 59 omega   31.00   62.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       64.0000   77.0000   98.8919 31

#__ type_ start__ end____ width___ exp.time_
 60 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   69.0000  -25.0979 27

#__ type_ start__ end____ width___ exp.time_
 61 omega   35.00   61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000  -18.2266 26

#__ type_ start__ end____ width___ exp.time_
 62 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000 -168.7121 26

#__ type_ start__ end____ width___ exp.time_
 63 omega   34.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   77.0000   43.8619 26

#__ type_ start__ end____ width___ exp.time_
 64 omega   37.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       68.0000   75.0000 -117.9934 26

#__ type_ start__ end____ width___ exp.time_
 65 omega   49.00   75.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       80.0000   66.0000  128.4412 26

#__ type_ start__ end____ width___ exp.time_
 66 omega   51.00   77.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   77.0000   -6.0322 26

#__ type_ start__ end____ width___ exp.time_
 67 omega  106.00  132.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   77.0000   -6.0322 26

#__ type_ start__ end____ width___ exp.time_
 68 omega   53.00  122.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   67.0000  -46.0114 69

#__ type_ start__ end____ width___ exp.time_
 69 omega   55.00   82.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   58.0000 -110.1536 27

#__ type_ start__ end____ width___ exp.time_
 70 omega   55.00   81.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       84.0000   60.0000  159.5952 26

#__ type_ start__ end____ width___ exp.time_
 71 omega   59.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   61.0000   69.2614 25

#__ type_ start__ end____ width___ exp.time_
 72 omega   58.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       88.0000   65.0000   28.6086 26

#__ type_ start__ end____ width___ exp.time_
 73 omega   65.00   91.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       96.0000   73.0000 -176.4796 26

#__ type_ start__ end____ width___ exp.time_
 74 omega   68.00   94.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      100.0000   70.0000  158.1785 26

#__ type_ start__ end____ width___ exp.time_
 75 omega   79.00  107.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 76 omega   79.00  152.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000    0.0000 73

#__ type_ start__ end____ width___ exp.time_
 77 omega  111.00  137.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 78 omega  134.00  160.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 79 omega   79.00  110.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 80 omega   85.00  121.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
 81 omega   83.00  114.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   62.0000 -116.4085 31

#__ type_ start__ end____ width___ exp.time_
 82 omega   80.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 83 omega   79.00  126.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 84 omega  117.00  144.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 85 omega   84.00  146.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 86 omega   79.00  111.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 87 omega   79.00  135.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 88 omega   90.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 89 omega   79.00  117.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 90 omega   79.00  134.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 91 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 92 omega  118.00  154.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
 93 omega   79.00  140.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000  -30.0000 61

#__ type_ start__ end____ width___ exp.time_
 94 omega   81.00  133.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   30.0000 52

#__ type_ start__ end____ width___ exp.time_
 95 omega   86.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 96 omega  125.00  151.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 97 omega   84.00  109.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 98 omega  122.00  148.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 99 omega   79.00  105.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
100 omega  113.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
101 omega   83.00  119.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   61.0000  -30.0000 36
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0664521000
_diffrn_orient_matrix_UB_12      0.0669489000
_diffrn_orient_matrix_UB_13      -0.0863468000
_diffrn_orient_matrix_UB_21      -0.1148378000
_diffrn_orient_matrix_UB_22      -0.0577389000
_diffrn_orient_matrix_UB_23      0.0409388000
_diffrn_orient_matrix_UB_31      -0.1156540000
_diffrn_orient_matrix_UB_32      0.1360270000
_diffrn_orient_matrix_UB_33      0.0685321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4739
_reflns_number_total             5224
_reflns_odcompleteness_completeness 94.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    ?
_refine_diff_density_max         0.769
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5224
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²+0.5611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1386
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O1-H1
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25), C26(H26),
  C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.38084(4) 0.09106(3) 0.91552(3) 0.08171(16) Uani 1 1 d . . . . .
O1 O -0.0423(2) 0.5237(2) 0.74053(15) 0.0653(5) Uani 1 1 d D . . . .
N1 N 0.18490(16) 0.52740(17) 0.70062(11) 0.0359(3) Uani 1 1 d . . . . .
N2 N 0.0476(2) 0.71900(19) 0.86251(16) 0.0505(4) Uani 1 1 d . . . . .
N3 N 0.0306(2) 0.6622(2) 0.61159(14) 0.0470(4) Uani 1 1 d . . . . .
C1 C 0.1064(2) 0.8006(2) 0.85010(16) 0.0432(4) Uani 1 1 d . . . . .
C2 C 0.0473(2) 0.5699(2) 0.68812(15) 0.0401(4) Uani 1 1 d . . . . .
C4 C -0.1112(2) 0.7254(2) 0.59119(16) 0.0443(4) Uani 1 1 d . . . . .
C5 C 0.1437(2) 0.7042(2) 0.55450(15) 0.0421(4) Uani 1 1 d . . . . .
C6 C 0.1933(2) 0.4772(2) 0.79632(15) 0.0415(4) Uani 1 1 d . . . . .
C7 C 0.1335(2) 0.5741(2) 0.87689(17) 0.0442(4) Uani 1 1 d . . . . .
C8 C 0.1491(3) 0.5234(3) 0.97035(18) 0.0521(5) Uani 1 1 d . . . . .
H8 H 0.1100 0.5865 1.0255 0.063 Uiso 1 1 calc R . . . .
C9 C 0.2221(3) 0.3803(3) 0.98218(18) 0.0524(5) Uani 1 1 d . . . . .
H9 H 0.2308 0.3469 1.0451 0.063 Uiso 1 1 calc R . . . .
C10 C 0.2814(2) 0.2879(2) 0.89976(18) 0.0477(5) Uani 1 1 d . . . . .
C11 C 0.2687(2) 0.3345(2) 0.80567(16) 0.0454(4) Uani 1 1 d . . . . .
H11 H 0.3100 0.2711 0.7503 0.054 Uiso 1 1 calc R . . . .
C12 C 0.2653(2) 0.7485(2) 0.85035(16) 0.0434(4) Uani 1 1 d . . . . .
C13 C 0.2911(3) 0.7644(3) 0.9373(2) 0.0640(7) Uani 1 1 d . . . . .
H13 H 0.2090 0.8174 0.9941 0.077 Uiso 1 1 calc R . . . .
C14 C 0.4379(3) 0.7022(4) 0.9405(2) 0.0742(8) Uani 1 1 d . . . . .
H14 H 0.4543 0.7137 0.9993 0.089 Uiso 1 1 calc R . . . .
C15 C 0.5599(3) 0.6232(3) 0.8570(2) 0.0697(7) Uani 1 1 d . . . . .
H15 H 0.6585 0.5790 0.8598 0.084 Uiso 1 1 calc R . . . .
C16 C 0.5357(3) 0.6100(3) 0.7698(2) 0.0687(7) Uani 1 1 d . . . . .
H16 H 0.6185 0.5588 0.7126 0.082 Uiso 1 1 calc R . . . .
C17 C 0.3885(3) 0.6725(3) 0.76580(18) 0.0561(5) Uani 1 1 d . . . . .
H17 H 0.3729 0.6631 0.7062 0.067 Uiso 1 1 calc R . . . .
C18 C 0.0165(3) 0.9498(2) 0.82970(16) 0.0469(4) Uani 1 1 d . . . . .
C19 C 0.0789(3) 1.0408(3) 0.8090(2) 0.0673(7) Uani 1 1 d . . . . .
H19 H 0.1758 1.0099 0.8122 0.081 Uiso 1 1 calc R . . . .
C20 C -0.0020(4) 1.1770(3) 0.7837(3) 0.0893(10) Uani 1 1 d . . . . .
H20 H 0.0392 1.2382 0.7715 0.107 Uiso 1 1 calc R . . . .
C21 C -0.1438(4) 1.2215(3) 0.7766(3) 0.0874(10) Uani 1 1 d . . . . .
H21 H -0.1966 1.3118 0.7569 0.105 Uiso 1 1 calc R . . . .
C22 C -0.2082(4) 1.1335(3) 0.7985(2) 0.0742(8) Uani 1 1 d . . . . .
H22 H -0.3047 1.1648 0.7944 0.089 Uiso 1 1 calc R . . . .
C23 C -0.1296(3) 0.9985(3) 0.82645(19) 0.0566(5) Uani 1 1 d . . . . .
H23 H -0.1746 0.9401 0.8432 0.068 Uiso 1 1 calc R . . . .
C24 C -0.2461(3) 0.8128(3) 0.6637(2) 0.0568(5) Uani 1 1 d . . . . .
H24 H -0.2461 0.8338 0.7263 0.068 Uiso 1 1 calc R . . . .
C25 C -0.3825(3) 0.8700(3) 0.6436(3) 0.0707(7) Uani 1 1 d . . . . .
H25 H -0.4739 0.9287 0.6929 0.085 Uiso 1 1 calc R . . . .
C26 C -0.3823(4) 0.8397(3) 0.5509(3) 0.0781(9) Uani 1 1 d . . . . .
H26 H -0.4738 0.8774 0.5378 0.094 Uiso 1 1 calc R . . . .
C27 C -0.2482(4) 0.7545(4) 0.4780(3) 0.0786(9) Uani 1 1 d . . . . .
H27 H -0.2488 0.7350 0.4152 0.094 Uiso 1 1 calc R . . . .
C28 C -0.1108(3) 0.6967(3) 0.4969(2) 0.0636(6) Uani 1 1 d . . . . .
H28 H -0.0195 0.6393 0.4469 0.076 Uiso 1 1 calc R . . . .
C29 C 0.2836(3) 0.6087(3) 0.48922(19) 0.0569(5) Uani 1 1 d . . . . .
H29 H 0.3069 0.5151 0.4832 0.068 Uiso 1 1 calc R . . . .
C30 C 0.3890(3) 0.6525(3) 0.4328(2) 0.0670(7) Uani 1 1 d . . . . .
H30 H 0.4837 0.5878 0.3896 0.080 Uiso 1 1 calc R . . . .
C31 C 0.3548(3) 0.7910(3) 0.4402(2) 0.0636(6) Uani 1 1 d . . . . .
H31 H 0.4253 0.8203 0.4011 0.076 Uiso 1 1 calc R . . . .
C32 C 0.2159(3) 0.8861(3) 0.5057(2) 0.0644(6) Uani 1 1 d . . . . .
H32 H 0.1930 0.9796 0.5116 0.077 Uiso 1 1 calc R . . . .
C33 C 0.1103(3) 0.8429(3) 0.56276(19) 0.0540(5) Uani 1 1 d . . . . .
H33 H 0.0165 0.9075 0.6069 0.065 Uiso 1 1 calc R . . . .
H1 H -0.129(3) 0.561(3) 0.717(3) 0.077(9) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C10 1.899(2) . ?
O1 C2 1.257(3) . ?
O1 H1 0.975(18) . ?
N1 C2 1.371(2) . ?
N1 C6 1.401(2) . ?
N2 C1 1.276(3) . ?
N2 C7 1.420(3) . ?
N3 C2 1.376(3) . ?
N3 C4 1.437(3) . ?
N3 C5 1.437(3) . ?
C1 C12 1.496(3) . ?
C1 C18 1.485(3) . ?
C4 C24 1.373(3) . ?
C4 C28 1.388(3) . ?
C5 C29 1.382(3) . ?
C5 C33 1.380(3) . ?
C6 C7 1.385(3) . ?
C6 C11 1.375(3) . ?
C7 C8 1.391(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(4) . ?
C10 C11 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 C17 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.380(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.389(4) . ?
C18 C23 1.390(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.383(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.375(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.382(4) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C25 1.389(4) . ?
C25 H25 0.9300 . ?
C25 C26 1.372(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.366(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.388(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C29 C30 1.383(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.374(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.377(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.382(4) . ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109(2) . . ?
C2 N1 C6 114.92(15) . . ?
C1 N2 C7 119.95(18) . . ?
C2 N3 C4 118.02(17) . . ?
C2 N3 C5 123.71(16) . . ?
C5 N3 C4 118.19(16) . . ?
N2 C1 C12 121.87(19) . . ?
N2 C1 C18 118.56(19) . . ?
C18 C1 C12 119.50(18) . . ?
O1 C2 N1 121.59(18) . . ?
O1 C2 N3 128.70(19) . . ?
N1 C2 N3 109.69(16) . . ?
C24 C4 N3 120.85(19) . . ?
C24 C4 C28 119.9(2) . . ?
C28 C4 N3 119.2(2) . . ?
C29 C5 N3 120.9(2) . . ?
C33 C5 N3 119.5(2) . . ?
C33 C5 C29 119.6(2) . . ?
C7 C6 N1 118.43(18) . . ?
C11 C6 N1 119.19(19) . . ?
C11 C6 C7 122.24(19) . . ?
C6 C7 N2 118.35(19) . . ?
C6 C7 C8 118.1(2) . . ?
C8 C7 N2 123.3(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C9 C10 Br1 119.45(16) . . ?
C9 C10 C11 121.7(2) . . ?
C11 C10 Br1 118.88(18) . . ?
C6 C11 C10 118.1(2) . . ?
C6 C11 H11 121.0 . . ?
C10 C11 H11 121.0 . . ?
C13 C12 C1 120.88(19) . . ?
C17 C12 C1 119.78(19) . . ?
C17 C12 C13 119.1(2) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(2) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.5(2) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 C16 120.0(2) . . ?
C12 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C1 120.9(2) . . ?
C19 C18 C23 118.9(2) . . ?
C23 C18 C1 120.0(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.5(3) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.2 . . ?
C21 C20 C19 119.7(3) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C4 C24 H24 120.0 . . ?
C4 C24 C25 120.0(2) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 119.9 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C4 C28 C27 119.3(3) . . ?
C4 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
C5 C29 H29 120.1 . . ?
C5 C29 C30 119.9(2) . . ?
C30 C29 H29 120.1 . . ?
C29 C30 H30 119.8 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.8 . . ?
C30 C31 H31 120.1 . . ?
C30 C31 C32 119.7(2) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.1(2) . . ?
C33 C32 H32 119.9 . . ?
C5 C33 C32 120.2(2) . . ?
C5 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?

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
Br1 C10 C11 C6 178.51(15) . . . . ?
N1 C6 C7 N2 8.9(3) . . . . ?
N1 C6 C7 C8 -176.85(17) . . . . ?
N1 C6 C11 C10 177.09(17) . . . . ?
N2 C1 C12 C13 -97.7(3) . . . . ?
N2 C1 C12 C17 76.6(3) . . . . ?
N2 C1 C18 C19 -175.8(2) . . . . ?
N2 C1 C18 C23 1.3(3) . . . . ?
N2 C7 C8 C9 173.88(19) . . . . ?
N3 C4 C24 C25 -178.3(2) . . . . ?
N3 C4 C28 C27 178.2(2) . . . . ?
N3 C5 C29 C30 178.1(2) . . . . ?
N3 C5 C33 C32 -177.8(2) . . . . ?
C1 N2 C7 C6 -104.8(2) . . . . ?
C1 N2 C7 C8 81.2(3) . . . . ?
C1 C12 C13 C14 172.6(3) . . . . ?
C1 C12 C17 C16 -172.6(2) . . . . ?
C1 C18 C19 C20 175.9(3) . . . . ?
C1 C18 C23 C22 -174.2(2) . . . . ?
C2 N1 C6 C7 -81.6(2) . . . . ?
C2 N1 C6 C11 102.5(2) . . . . ?
C2 N3 C4 C24 63.4(3) . . . . ?
C2 N3 C4 C28 -116.4(2) . . . . ?
C2 N3 C5 C29 66.9(3) . . . . ?
C2 N3 C5 C33 -115.0(2) . . . . ?
C4 N3 C2 O1 5.3(3) . . . . ?
C4 N3 C2 N1 -176.29(18) . . . . ?
C4 N3 C5 C29 -116.3(2) . . . . ?
C4 N3 C5 C33 61.8(3) . . . . ?
C4 C24 C25 C26 -0.4(4) . . . . ?
C5 N3 C2 O1 -178.0(2) . . . . ?
C5 N3 C2 N1 0.5(3) . . . . ?
C5 N3 C4 C24 -113.5(2) . . . . ?
C5 N3 C4 C28 66.7(3) . . . . ?
C5 C29 C30 C31 -0.8(4) . . . . ?
C6 N1 C2 O1 -23.7(3) . . . . ?
C6 N1 C2 N3 157.73(18) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 N2 C1 C12 -0.1(3) . . . . ?
C7 N2 C1 C18 176.75(19) . . . . ?
C7 C6 C11 C10 1.4(3) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C9 C10 Br1 -179.65(16) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
C11 C6 C7 N2 -175.37(18) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C12 C1 C18 C19 1.2(3) . . . . ?
C12 C1 C18 C23 178.21(19) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?
C13 C12 C17 C16 1.7(4) . . . . ?
C13 C14 C15 C16 2.0(5) . . . . ?
C14 C15 C16 C17 -1.8(5) . . . . ?
C15 C16 C17 C12 0.0(5) . . . . ?
C17 C12 C13 C14 -1.6(4) . . . . ?
C18 C1 C12 C13 85.5(3) . . . . ?
C18 C1 C12 C17 -100.3(2) . . . . ?
C18 C19 C20 C21 -1.6(5) . . . . ?
C19 C18 C23 C22 2.9(4) . . . . ?
C19 C20 C21 C22 2.6(6) . . . . ?
C20 C21 C22 C23 -0.9(5) . . . . ?
C21 C22 C23 C18 -1.9(4) . . . . ?
C23 C18 C19 C20 -1.2(4) . . . . ?
C24 C4 C28 C27 -1.5(4) . . . . ?
C24 C25 C26 C27 -0.6(5) . . . . ?
C25 C26 C27 C28 0.5(5) . . . . ?
C26 C27 C28 C4 0.6(5) . . . . ?
C28 C4 C24 C25 1.5(4) . . . . ?
C29 C5 C33 C32 0.3(4) . . . . ?
C29 C30 C31 C32 1.3(5) . . . . ?
C30 C31 C32 C33 -0.9(4) . . . . ?
C31 C32 C33 C5 0.1(4) . . . . ?
C33 C5 C29 C30 0.0(4) . . . . ?

# start Validation Reply Form
_vrf_PLAT230_6ed                 
;
PROBLEM: Hirshfeld Test Diff for    O1     --  C2      ..        9.2 su    
RESPONSE: Diffraction data have been collected at room temerature
conditions due to the crystal's quality degradation at cooling sample.
Thus, slight increase of adp's, especially for several atoms, is observed.
;
_vrf_PLAT420_6ed                 
;
PROBLEM: D-H Without Acceptor        O1     -   H1     ..     Please Check 
RESPONSE: Hydrogen atom was located from the difference Fourier map
(residual density peak higher than others was well observed).  
;
# end Validation Reply Form
