# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
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# Crystallographic Data Centre (CCDC).
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_mx3405
_database_code_depnum_ccdc_archive 'CCDC 1455366'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H20 N4 O2'
_chemical_formula_sum            'C24 H20 N4 O2'
_chemical_formula_weight         396.44
_chemical_absolute_configuration ?
_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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   11.285(2)
_cell_length_b                   14.466(3)
_cell_length_c                   13.528(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.20(3)
_cell_angle_gamma                90
_cell_volume                     2044.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7622
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4813
_cell_measurement_theta_min      1.4076
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24275
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4884
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0646
_diffrn_orient_matrix_UB_12      -0.0687
_diffrn_orient_matrix_UB_13      -0.0167
_diffrn_orient_matrix_UB_21      0.0027
_diffrn_orient_matrix_UB_22      -0.0139
_diffrn_orient_matrix_UB_23      0.0677
_diffrn_orient_matrix_UB_31      -0.0341
_diffrn_orient_matrix_UB_32      -0.0710
_diffrn_orient_matrix_UB_33      -0.0132
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.931
_reflns_Friedel_fraction_max     0.913
_reflns_number_gt                8603
_reflns_number_total             8978
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3628 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.7(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     543
_refine_ls_number_reflns         8978
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.037
_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)+(0.0380P)²+0.5320P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1027
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C32(H32)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C18(H18A,H18B), C33(H33A,H33B), C40(H40A,H40B),
 C42(H42A,H42B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C26(H26), C27(H27), C28(H28), C29(H29), C31(H31), C44(H44),
  C45(H45), C46(H46), C47(H47), C48(H48)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 -0.3751(2) -0.21771(15) -0.25830(17) 0.0443(5) Uani 1 1 d . . . . .
O2 O -0.5679(2) -0.28665(15) -0.31833(17) 0.0433(5) Uani 1 1 d . . . . .
N1 N -0.2737(2) 0.11731(17) -0.28083(18) 0.0359(5) Uani 1 1 d . . . . .
N2 N -0.3865(2) 0.06824(15) -0.33767(16) 0.0289(5) Uani 1 1 d . . . . .
N3 N -0.3710(3) -0.04100(18) -0.11681(19) 0.0397(6) Uani 1 1 d . . . . .
N4 N -0.1719(3) -0.0978(2) -0.3337(2) 0.0479(7) Uani 1 1 d . . . . .
C1 C -0.5658(3) 0.2107(2) -0.5676(2) 0.0426(7) Uani 1 1 d . . . . .
H1 H -0.6245 0.1702 -0.6142 0.051 Uiso 1 1 calc R . . . .
C2 C -0.5790(3) 0.3051(2) -0.5857(3) 0.0470(8) Uani 1 1 d . . . . .
H2 H -0.6468 0.3277 -0.6444 0.056 Uiso 1 1 calc R . . . .
C3 C -0.4919(3) 0.3661(2) -0.5170(3) 0.0474(8) Uani 1 1 d . . . . .
H3 H -0.5014 0.4294 -0.5295 0.057 Uiso 1 1 calc R . . . .
C4 C -0.3903(3) 0.3324(2) -0.4294(2) 0.0437(7) Uani 1 1 d . . . . .
H4 H -0.3311 0.3732 -0.3835 0.052 Uiso 1 1 calc R . . . .
C5 C -0.3770(3) 0.2383(2) -0.4102(2) 0.0355(6) Uani 1 1 d . . . . .
C6 C -0.4653(3) 0.17681(19) -0.4802(2) 0.0327(6) Uani 1 1 d . . . . .
C7 C -0.4370(3) 0.07626(19) -0.4548(2) 0.0307(6) Uani 1 1 d . . . . .
H7 H -0.3723 0.0554 -0.4818 0.037 Uiso 1 1 calc R . . . .
C8 C -0.2727(3) 0.1988(2) -0.3178(2) 0.0383(7) Uani 1 1 d . . . . .
H8 H -0.2011 0.2355 -0.2838 0.046 Uiso 1 1 calc R . . . .
C9 C -0.5465(3) 0.00693(19) -0.4855(2) 0.0309(5) Uani 1 1 d . . . . .
H9A H -0.6235 0.0353 -0.4836 0.037 Uiso 1 1 calc R . . . .
H9B H -0.5646 -0.0176 -0.5564 0.037 Uiso 1 1 calc R . . . .
C10 C -0.4985(2) -0.06839(18) -0.40193(19) 0.0285(5) Uani 1 1 d . . . . .
C11 C -0.3774(2) -0.03011(17) -0.3118(2) 0.0287(5) Uani 1 1 d . . . . .
C12 C -0.3738(3) -0.04054(18) -0.2016(2) 0.0308(6) Uani 1 1 d . . . . .
C13 C -0.2604(3) -0.0718(2) -0.3208(2) 0.0347(6) Uani 1 1 d . . . . .
C14 C -0.5468(3) -0.15280(19) -0.4060(2) 0.0305(5) Uani 1 1 d . . . . .
C15 C -0.4853(3) -0.2217(2) -0.3186(2) 0.0346(6) Uani 1 1 d . . . . .
C16 C -0.5186(4) -0.3647(2) -0.2460(3) 0.0517(8) Uani 1 1 d . . . . .
H16A H -0.5857 -0.3898 -0.2256 0.062 Uiso 1 1 calc R . . . .
H16B H -0.4490 -0.3444 -0.1819 0.062 Uiso 1 1 calc R . . . .
C17 C -0.4724(5) -0.4363(3) -0.3000(4) 0.0737(13) Uani 1 1 d . . . . .
H17A H -0.5393 -0.4522 -0.3666 0.111 Uiso 1 1 calc GR . . . .
H17B H -0.4478 -0.4903 -0.2554 0.111 Uiso 1 1 calc GR . . . .
H17C H -0.3998 -0.4133 -0.3130 0.111 Uiso 1 1 calc GR . . . .
C18 C -0.6592(3) -0.18763(19) -0.5012(2) 0.0320(6) Uani 1 1 d . . . . .
H18A H -0.6941 -0.1373 -0.5512 0.038 Uiso 1 1 calc R . . . .
H18B H -0.7257 -0.2091 -0.4777 0.038 Uiso 1 1 calc R . . . .
C19 C -0.6200(2) -0.26590(18) -0.55696(19) 0.0283(5) Uani 1 1 d . . . . .
C20 C -0.5052(3) -0.2633(2) -0.5709(2) 0.0377(6) Uani 1 1 d . . . . .
H20 H -0.4494 -0.2142 -0.5428 0.045 Uiso 1 1 calc R . . . .
C21 C -0.4715(4) -0.3327(3) -0.6262(3) 0.0533(9) Uani 1 1 d . . . . .
H21 H -0.3939 -0.3299 -0.6354 0.064 Uiso 1 1 calc R . . . .
C22 C -0.5542(4) -0.4059(2) -0.6676(3) 0.0559(10) Uani 1 1 d . . . . .
H22 H -0.5329 -0.4522 -0.7056 0.067 Uiso 1 1 calc R . . . .
C23 C -0.6668(4) -0.4102(2) -0.6525(3) 0.0553(10) Uani 1 1 d . . . . .
H23 H -0.7212 -0.4602 -0.6792 0.066 Uiso 1 1 calc R . . . .
C24 C -0.7009(3) -0.3408(2) -0.5979(2) 0.0417(7) Uani 1 1 d . . . . .
H24 H -0.7783 -0.3443 -0.5886 0.050 Uiso 1 1 calc R . . . .
O3 O -0.1574(2) -0.38125(16) -0.61759(18) 0.0530(6) Uani 1 1 d . . . . .
O4 O -0.1052(3) -0.29381(17) -0.73015(18) 0.0733(9) Uani 1 1 d . . . . .
N5 N 0.1443(2) -0.43491(16) -0.23404(18) 0.0353(5) Uani 1 1 d . . . . .
N6 N 0.1288(2) -0.35810(15) -0.30053(18) 0.0319(5) Uani 1 1 d . . . . .
N7 N 0.1053(3) -0.4924(2) -0.5093(3) 0.0557(8) Uani 1 1 d . . . . .
N8 N -0.1840(3) -0.4200(2) -0.3829(3) 0.0568(8) Uani 1 1 d . . . . .
C25 C 0.2256(3) -0.2511(2) -0.1594(2) 0.0358(6) Uani 1 1 d . . . . .
C26 C 0.2788(3) -0.1648(2) -0.1261(2) 0.0449(8) Uani 1 1 d . . . . .
H26 H 0.2481 -0.1134 -0.1695 0.054 Uiso 1 1 calc R . . . .
C27 C 0.3784(4) -0.1556(3) -0.0272(3) 0.0541(9) Uani 1 1 d . . . . .
H27 H 0.4149 -0.0979 -0.0046 0.065 Uiso 1 1 calc R . . . .
C28 C 0.4234(4) -0.2321(3) 0.0378(3) 0.0518(8) Uani 1 1 d . . . . .
H28 H 0.4887 -0.2252 0.1045 0.062 Uiso 1 1 calc R . . . .
C29 C 0.3720(3) -0.3182(2) 0.0041(2) 0.0446(7) Uani 1 1 d . . . . .
H29 H 0.4032 -0.3694 0.0479 0.053 Uiso 1 1 calc R . . . .
C30 C 0.2729(3) -0.3292(2) -0.0959(2) 0.0355(6) Uani 1 1 d . . . . .
C31 C 0.2162(3) -0.4185(2) -0.1360(2) 0.0384(7) Uani 1 1 d . . . . .
H31 H 0.2329 -0.4671 -0.0877 0.046 Uiso 1 1 calc R . . . .
C32 C 0.1112(3) -0.26808(18) -0.2601(2) 0.0327(6) Uani 1 1 d . . . . .
H32 H 0.0335 -0.2686 -0.2441 0.039 Uiso 1 1 calc R . . . .
C33 C 0.0905(3) -0.20697(17) -0.3570(2) 0.0296(5) Uani 1 1 d . . . . .
H33A H 0.0395 -0.1531 -0.3567 0.036 Uiso 1 1 calc R . . . .
H33B H 0.1715 -0.1868 -0.3591 0.036 Uiso 1 1 calc R . . . .
C34 C 0.0199(3) -0.26989(17) -0.4506(2) 0.0300(5) Uani 1 1 d . . . . .
C35 C 0.0270(3) -0.36904(17) -0.4060(2) 0.0307(6) Uani 1 1 d . . . . .
C36 C 0.0683(3) -0.43935(19) -0.4653(2) 0.0378(7) Uani 1 1 d . . . . .
C37 C -0.0958(3) -0.39755(19) -0.3974(2) 0.0362(6) Uani 1 1 d . . . . .
C38 C -0.0330(3) -0.24527(18) -0.5532(2) 0.0328(6) Uani 1 1 d . . . . .
C39 C -0.1047(3) -0.3149(2) -0.6357(2) 0.0385(7) Uani 1 1 d . . . . .
C40 C -0.1873(8) -0.3503(3) -0.8205(3) 0.121(3) Uani 1 1 d . . . . .
H40A H -0.1348 -0.3948 -0.8391 0.145 Uiso 1 1 calc R . . . .
H40B H -0.2479 -0.3843 -0.7993 0.145 Uiso 1 1 calc R . . . .
C41 C -0.2518(6) -0.2982(4) -0.9068(5) 0.121(3) Uani 1 1 d . . . . .
H41A H -0.2824 -0.3368 -0.9691 0.181 Uiso 1 1 calc GR . . . .
H41B H -0.1959 -0.2518 -0.9156 0.181 Uiso 1 1 calc GR . . . .
H41C H -0.3231 -0.2691 -0.8971 0.181 Uiso 1 1 calc GR . . . .
C42 C -0.0270(3) -0.14812(19) -0.5919(2) 0.0367(6) Uani 1 1 d . . . . .
H42A H 0.0125 -0.1082 -0.5306 0.044 Uiso 1 1 calc R . . . .
H42B H 0.0270 -0.1479 -0.6332 0.044 Uiso 1 1 calc R . . . .
C43 C -0.1562(3) -0.10906(17) -0.6596(2) 0.0301(6) Uani 1 1 d . . . . .
C44 C -0.2555(3) -0.1074(2) -0.6225(2) 0.0408(7) Uani 1 1 d . . . . .
H44 H -0.2413 -0.1284 -0.5540 0.049 Uiso 1 1 calc R . . . .
C45 C -0.3758(3) -0.0745(2) -0.6870(3) 0.0462(7) Uani 1 1 d . . . . .
H45 H -0.4416 -0.0740 -0.6614 0.055 Uiso 1 1 calc R . . . .
C46 C -0.3981(3) -0.0430(2) -0.7880(2) 0.0410(7) Uani 1 1 d . . . . .
H46 H -0.4786 -0.0207 -0.8306 0.049 Uiso 1 1 calc R . . . .
C47 C -0.3010(3) -0.0442(2) -0.8260(2) 0.0391(7) Uani 1 1 d . . . . .
H47 H -0.3156 -0.0229 -0.8945 0.047 Uiso 1 1 calc R . . . .
C48 C -0.1815(3) -0.07734(19) -0.7624(2) 0.0356(6) Uani 1 1 d . . . . .
H48 H -0.1167 -0.0784 -0.7890 0.043 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 C15 1.205(4) . ?
O2 C15 1.325(4) . ?
O2 C16 1.460(4) . ?
N1 N2 1.406(3) . ?
N1 C8 1.283(4) . ?
N2 C7 1.472(3) . ?
N2 C11 1.459(3) . ?
N3 C12 1.135(4) . ?
N4 C13 1.140(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C1 C6 1.383(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(4) . ?
C5 C6 1.403(4) . ?
C5 C8 1.470(4) . ?
C6 C7 1.501(4) . ?
C7 H7 0.9800 . ?
C7 C9 1.523(4) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.515(4) . ?
C10 C11 1.550(3) . ?
C10 C14 1.330(4) . ?
C11 C12 1.484(4) . ?
C11 C13 1.498(4) . ?
C14 C15 1.500(4) . ?
C14 C18 1.512(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.471(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.517(4) . ?
C19 C20 1.378(4) . ?
C19 C24 1.390(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.388(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.362(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(5) . ?
C24 H24 0.9300 . ?
O3 C39 1.202(4) . ?
O4 C39 1.312(4) . ?
O4 C40 1.471(5) . ?
N5 N6 1.398(3) . ?
N5 C31 1.288(4) . ?
N6 C32 1.455(3) . ?
N6 C35 1.464(3) . ?
N7 C36 1.142(4) . ?
N8 C37 1.133(4) . ?
C25 C26 1.385(4) . ?
C25 C30 1.397(4) . ?
C25 C32 1.501(4) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(5) . ?
C27 H27 0.9300 . ?
C27 C28 1.384(5) . ?
C28 H28 0.9300 . ?
C28 C29 1.378(5) . ?
C29 H29 0.9300 . ?
C29 C30 1.401(4) . ?
C30 C31 1.454(4) . ?
C31 H31 0.9300 . ?
C32 H32 0.9800 . ?
C32 C33 1.525(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C34 1.518(4) . ?
C34 C35 1.546(3) . ?
C34 C38 1.335(4) . ?
C35 C36 1.476(4) . ?
C35 C37 1.493(4) . ?
C38 C39 1.494(4) . ?
C38 C42 1.510(4) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.349(7) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C42 C43 1.508(4) . ?
C43 C44 1.390(4) . ?
C43 C48 1.387(4) . ?
C44 H44 0.9300 . ?
C44 C45 1.391(5) . ?
C45 H45 0.9300 . ?
C45 C46 1.371(5) . ?
C46 H46 0.9300 . ?
C46 C47 1.376(5) . ?
C47 H47 0.9300 . ?
C47 C48 1.382(4) . ?
C48 H48 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
C15 O2 C16 117.4(3) . . ?
C8 N1 N2 113.0(2) . . ?
N1 N2 C7 116.8(2) . . ?
N1 N2 C11 113.2(2) . . ?
C11 N2 C7 107.37(19) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C6 C1 C2 120.0(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 C8 122.5(3) . . ?
C6 C5 C8 117.7(3) . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C7 125.1(3) . . ?
C5 C6 C7 115.1(2) . . ?
N2 C7 C6 106.6(2) . . ?
N2 C7 H7 109.7 . . ?
N2 C7 C9 100.7(2) . . ?
C6 C7 H7 109.7 . . ?
C6 C7 C9 119.7(2) . . ?
C9 C7 H7 109.7 . . ?
N1 C8 C5 124.5(3) . . ?
N1 C8 H8 117.8 . . ?
C5 C8 H8 117.8 . . ?
C7 C9 H9A 110.9 . . ?
C7 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C7 104.2(2) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 C11 106.9(2) . . ?
C14 C10 C9 127.2(2) . . ?
C14 C10 C11 125.9(2) . . ?
N2 C11 C10 101.4(2) . . ?
N2 C11 C12 108.2(2) . . ?
N2 C11 C13 111.0(2) . . ?
C12 C11 C10 115.8(2) . . ?
C12 C11 C13 110.5(2) . . ?
C13 C11 C10 109.5(2) . . ?
N3 C12 C11 174.5(3) . . ?
N4 C13 C11 174.2(3) . . ?
C10 C14 C15 121.1(2) . . ?
C10 C14 C18 122.7(2) . . ?
C15 C14 C18 116.0(2) . . ?
O1 C15 O2 125.4(3) . . ?
O1 C15 C14 123.6(3) . . ?
O2 C15 C14 111.0(2) . . ?
O2 C16 H16A 109.8 . . ?
O2 C16 H16B 109.8 . . ?
O2 C16 C17 109.3(3) . . ?
H16A C16 H16B 108.3 . . ?
C17 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.4 . . ?
C14 C18 H18B 109.4 . . ?
C14 C18 C19 111.3(2) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 C24 118.5(3) . . ?
C24 C19 C18 120.6(3) . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.1(3) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.3 . . ?
C22 C21 C20 119.5(3) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.6(3) . . ?
C24 C23 H23 119.7 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.3(3) . . ?
C23 C24 H24 119.8 . . ?
C39 O4 C40 116.7(3) . . ?
C31 N5 N6 113.1(2) . . ?
N5 N6 C32 118.1(2) . . ?
N5 N6 C35 113.8(2) . . ?
C32 N6 C35 107.2(2) . . ?
C26 C25 C30 120.7(3) . . ?
C26 C25 C32 124.1(3) . . ?
C30 C25 C32 115.1(2) . . ?
C25 C26 H26 120.3 . . ?
C25 C26 C27 119.5(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(3) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 119.9 . . ?
C28 C29 C30 120.3(3) . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 118.9(3) . . ?
C25 C30 C31 118.5(3) . . ?
C29 C30 C31 122.6(3) . . ?
N5 C31 C30 124.4(3) . . ?
N5 C31 H31 117.8 . . ?
C30 C31 H31 117.8 . . ?
N6 C32 C25 107.2(2) . . ?
N6 C32 H32 109.6 . . ?
N6 C32 C33 101.2(2) . . ?
C25 C32 H32 109.6 . . ?
C25 C32 C33 119.0(2) . . ?
C33 C32 H32 109.6 . . ?
C32 C33 H33A 111.1 . . ?
C32 C33 H33B 111.1 . . ?
H33A C33 H33B 109.1 . . ?
C34 C33 C32 103.4(2) . . ?
C34 C33 H33A 111.1 . . ?
C34 C33 H33B 111.1 . . ?
C33 C34 C35 107.3(2) . . ?
C38 C34 C33 126.5(2) . . ?
C38 C34 C35 126.1(2) . . ?
N6 C35 C34 100.7(2) . . ?
N6 C35 C36 108.2(2) . . ?
N6 C35 C37 111.3(2) . . ?
C36 C35 C34 114.1(2) . . ?
C36 C35 C37 110.2(2) . . ?
C37 C35 C34 112.0(2) . . ?
N7 C36 C35 177.2(4) . . ?
N8 C37 C35 174.9(3) . . ?
C34 C38 C39 120.0(2) . . ?
C34 C38 C42 123.2(3) . . ?
C39 C38 C42 116.8(2) . . ?
O3 C39 O4 124.3(3) . . ?
O3 C39 C38 123.8(3) . . ?
O4 C39 C38 111.9(3) . . ?
O4 C40 H40A 109.2 . . ?
O4 C40 H40B 109.2 . . ?
H40A C40 H40B 107.9 . . ?
C41 C40 O4 111.9(4) . . ?
C41 C40 H40A 109.2 . . ?
C41 C40 H40B 109.2 . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C38 C42 H42A 108.9 . . ?
C38 C42 H42B 108.9 . . ?
H42A C42 H42B 107.7 . . ?
C43 C42 C38 113.6(2) . . ?
C43 C42 H42A 108.9 . . ?
C43 C42 H42B 108.9 . . ?
C44 C43 C42 120.9(2) . . ?
C48 C43 C42 121.2(3) . . ?
C48 C43 C44 117.8(3) . . ?
C43 C44 H44 119.7 . . ?
C43 C44 C45 120.6(3) . . ?
C45 C44 H44 119.7 . . ?
C44 C45 H45 119.8 . . ?
C46 C45 C44 120.4(3) . . ?
C46 C45 H45 119.8 . . ?
C45 C46 H46 120.1 . . ?
C45 C46 C47 119.7(3) . . ?
C47 C46 H46 120.1 . . ?
C46 C47 H47 120.0 . . ?
C46 C47 C48 119.9(3) . . ?
C48 C47 H47 120.0 . . ?
C43 C48 H48 119.3 . . ?
C47 C48 C43 121.5(3) . . ?
C47 C48 H48 119.3 . . ?

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 N2 C7 C6 -60.4(3) . . . . ?
N1 N2 C7 C9 174.0(2) . . . . ?
N1 N2 C11 C10 -167.6(2) . . . . ?
N1 N2 C11 C12 70.1(3) . . . . ?
N1 N2 C11 C13 -51.3(3) . . . . ?
N2 N1 C8 C5 -0.4(4) . . . . ?
N2 C7 C9 C10 -34.0(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
C1 C6 C7 N2 -145.1(3) . . . . ?
C1 C6 C7 C9 -32.0(4) . . . . ?
C2 C1 C6 C5 -0.1(5) . . . . ?
C2 C1 C6 C7 -176.9(3) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 0.8(5) . . . . ?
C3 C4 C5 C8 -179.0(3) . . . . ?
C4 C5 C6 C1 -0.5(4) . . . . ?
C4 C5 C6 C7 176.7(3) . . . . ?
C4 C5 C8 N1 161.0(3) . . . . ?
C5 C6 C7 N2 37.9(3) . . . . ?
C5 C6 C7 C9 151.0(3) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C6 C5 C8 N1 -18.7(5) . . . . ?
C6 C7 C9 C10 -150.3(2) . . . . ?
C7 N2 C11 C10 -37.2(3) . . . . ?
C7 N2 C11 C12 -159.5(2) . . . . ?
C7 N2 C11 C13 79.1(3) . . . . ?
C7 C9 C10 C11 12.7(3) . . . . ?
C7 C9 C10 C14 -164.8(3) . . . . ?
C8 N1 N2 C7 41.9(3) . . . . ?
C8 N1 N2 C11 167.4(2) . . . . ?
C8 C5 C6 C1 179.3(3) . . . . ?
C8 C5 C6 C7 -3.5(4) . . . . ?
C9 C10 C11 N2 13.9(3) . . . . ?
C9 C10 C11 C12 130.8(2) . . . . ?
C9 C10 C11 C13 -103.5(2) . . . . ?
C9 C10 C14 C15 177.5(3) . . . . ?
C9 C10 C14 C18 2.1(4) . . . . ?
C10 C14 C15 O1 -22.1(4) . . . . ?
C10 C14 C15 O2 158.6(3) . . . . ?
C10 C14 C18 C19 113.9(3) . . . . ?
C11 N2 C7 C6 171.2(2) . . . . ?
C11 N2 C7 C9 45.6(3) . . . . ?
C11 C10 C14 C15 0.5(4) . . . . ?
C11 C10 C14 C18 -174.9(2) . . . . ?
C14 C10 C11 N2 -168.6(3) . . . . ?
C14 C10 C11 C12 -51.7(4) . . . . ?
C14 C10 C11 C13 74.0(3) . . . . ?
C14 C18 C19 C20 -40.4(4) . . . . ?
C14 C18 C19 C24 141.5(3) . . . . ?
C15 O2 C16 C17 -87.6(4) . . . . ?
C15 C14 C18 C19 -61.6(3) . . . . ?
C16 O2 C15 O1 -6.3(4) . . . . ?
C16 O2 C15 C14 172.9(2) . . . . ?
C18 C14 C15 O1 153.5(3) . . . . ?
C18 C14 C15 O2 -25.8(3) . . . . ?
C18 C19 C20 C21 -177.0(3) . . . . ?
C18 C19 C24 C23 177.4(3) . . . . ?
C19 C20 C21 C22 -0.3(5) . . . . ?
C20 C19 C24 C23 -0.8(4) . . . . ?
C20 C21 C22 C23 -1.0(5) . . . . ?
C21 C22 C23 C24 1.3(5) . . . . ?
C22 C23 C24 C19 -0.4(5) . . . . ?
C24 C19 C20 C21 1.2(4) . . . . ?
N5 N6 C32 C25 57.8(3) . . . . ?
N5 N6 C32 C33 -176.8(2) . . . . ?
N5 N6 C35 C34 171.1(2) . . . . ?
N5 N6 C35 C36 -68.9(3) . . . . ?
N5 N6 C35 C37 52.3(3) . . . . ?
N6 N5 C31 C30 2.0(4) . . . . ?
N6 C32 C33 C34 33.9(3) . . . . ?
C25 C26 C27 C28 -0.5(6) . . . . ?
C25 C30 C31 N5 15.2(5) . . . . ?
C25 C32 C33 C34 150.9(2) . . . . ?
C26 C25 C30 C29 2.5(5) . . . . ?
C26 C25 C30 C31 -178.2(3) . . . . ?
C26 C25 C32 N6 146.6(3) . . . . ?
C26 C25 C32 C33 32.8(4) . . . . ?
C26 C27 C28 C29 1.5(6) . . . . ?
C27 C28 C29 C30 -0.5(6) . . . . ?
C28 C29 C30 C25 -1.5(5) . . . . ?
C28 C29 C30 C31 179.2(3) . . . . ?
C29 C30 C31 N5 -165.5(3) . . . . ?
C30 C25 C26 C27 -1.5(5) . . . . ?
C30 C25 C32 N6 -36.9(3) . . . . ?
C30 C25 C32 C33 -150.7(3) . . . . ?
C31 N5 N6 C32 -40.7(4) . . . . ?
C31 N5 N6 C35 -167.7(3) . . . . ?
C32 N6 C35 C34 38.7(3) . . . . ?
C32 N6 C35 C36 158.6(2) . . . . ?
C32 N6 C35 C37 -80.2(3) . . . . ?
C32 C25 C26 C27 174.8(3) . . . . ?
C32 C25 C30 C29 -174.2(3) . . . . ?
C32 C25 C30 C31 5.1(4) . . . . ?
C32 C33 C34 C35 -11.4(3) . . . . ?
C32 C33 C34 C38 171.7(3) . . . . ?
C33 C34 C35 N6 -15.3(3) . . . . ?
C33 C34 C35 C36 -131.0(3) . . . . ?
C33 C34 C35 C37 103.0(3) . . . . ?
C33 C34 C38 C39 -177.2(3) . . . . ?
C33 C34 C38 C42 1.5(5) . . . . ?
C34 C38 C39 O3 27.0(5) . . . . ?
C34 C38 C39 O4 -154.2(3) . . . . ?
C34 C38 C42 C43 -127.1(3) . . . . ?
C35 N6 C32 C25 -172.1(2) . . . . ?
C35 N6 C32 C33 -46.7(3) . . . . ?
C35 C34 C38 C39 6.5(5) . . . . ?
C35 C34 C38 C42 -174.9(3) . . . . ?
C38 C34 C35 N6 161.6(3) . . . . ?
C38 C34 C35 C36 46.0(4) . . . . ?
C38 C34 C35 C37 -80.0(4) . . . . ?
C38 C42 C43 C44 54.0(4) . . . . ?
C38 C42 C43 C48 -123.2(3) . . . . ?
C39 O4 C40 C41 137.1(6) . . . . ?
C39 C38 C42 C43 51.6(4) . . . . ?
C40 O4 C39 O3 6.7(6) . . . . ?
C40 O4 C39 C38 -172.0(4) . . . . ?
C42 C38 C39 O3 -151.7(3) . . . . ?
C42 C38 C39 O4 27.0(4) . . . . ?
C42 C43 C44 C45 -177.5(3) . . . . ?
C42 C43 C48 C47 177.9(3) . . . . ?
C43 C44 C45 C46 -0.3(5) . . . . ?
C44 C43 C48 C47 0.6(4) . . . . ?
C44 C45 C46 C47 0.4(5) . . . . ?
C45 C46 C47 C48 0.0(5) . . . . ?
C46 C47 C48 C43 -0.5(4) . . . . ?
C48 C43 C44 C45 -0.2(4) . . . . ?

####################################################################### 
# 
# 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_mx3423
_database_code_depnum_ccdc_archive 'CCDC 1455369'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-12-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H20 N3 O2, C25 H21 N3 O2'
_chemical_formula_sum            'C50 H41 N6 O4'
_chemical_formula_weight         789.89
_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                   16.156(3)
_cell_length_b                   10.118(2)
_cell_length_c                   25.816(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.14(3)
_cell_angle_gamma                90
_cell_volume                     4073.8(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12022
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4843
_cell_measurement_theta_min      1.3057
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1660
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            28360
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.306
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             9808
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0136
_diffrn_orient_matrix_UB_12      0.0118
_diffrn_orient_matrix_UB_13      -0.0616
_diffrn_orient_matrix_UB_21      -0.0660
_diffrn_orient_matrix_UB_22      0.0736
_diffrn_orient_matrix_UB_23      -0.0005
_diffrn_orient_matrix_UB_31      0.0299
_diffrn_orient_matrix_UB_32      0.0268
_diffrn_orient_matrix_UB_33      0.0008
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0000
_diffrn_source_power             1.2000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7997
_reflns_number_total             9274
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2013)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2013)'
_computing_structure_solution    
;
 'XS (Sheldrick, 2013)'
;
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     565
_refine_ls_number_reflns         9274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.8113P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1499
_refine_ls_wR_factor_ref         0.1583
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C9)=Sof(H9)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C9(H9), C34(H34), C9A(H9A)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C19(H19A,H19B), C35(H35A,H35B), C42(H42A,H42B), C44(H44A,H44B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C7(H7), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28), C29(H29), C32(H32), C46(H46),
  C47(H47), C48(H48), C49(H49), C50(H50)
3.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C43(H43A,H43B,H43C)
;
_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
O1 O 0.17598(10) 0.26243(14) 0.15371(7) 0.0458(4) Uani 1 1 d . . . . .
O2 O 0.19506(9) 0.04925(13) 0.13721(6) 0.0376(3) Uani 1 1 d . . . . .
N1 N -0.05556(12) 0.40179(17) 0.17400(10) 0.0525(6) Uani 1 1 d . . . . .
N2 N 0.14289(14) 0.43479(19) 0.24873(8) 0.0509(5) Uani 1 1 d . . . . .
N3 N 0.03930(13) 0.4442(2) 0.07325(8) 0.0522(5) Uani 1 1 d . . . . .
C1 C -0.27474(14) 0.5148(2) 0.21725(9) 0.0432(5) Uani 1 1 d . . . . .
H1 H -0.2883 0.6039 0.2186 0.052 Uiso 1 1 calc R . . . .
C2 C -0.32797(15) 0.4201(3) 0.22980(9) 0.0476(6) Uani 1 1 d . . . . .
H2 H -0.3773 0.4457 0.2393 0.057 Uiso 1 1 calc R . . . .
C3 C -0.30834(14) 0.2879(2) 0.22838(9) 0.0424(5) Uani 1 1 d . . . . .
H3 H -0.3441 0.2247 0.2373 0.051 Uiso 1 1 calc R . . . .
C4 C -0.23550(13) 0.2490(2) 0.21372(8) 0.0372(5) Uani 1 1 d . . . . .
H4 H -0.2224 0.1597 0.2126 0.045 Uiso 1 1 calc R . . . .
C5 C -0.18205(13) 0.3434(2) 0.20064(9) 0.0364(5) Uani 1 1 d . . . . .
C6 C -0.20096(13) 0.4782(2) 0.20258(8) 0.0354(4) Uani 1 1 d . . . . .
C7 C -0.14284(14) 0.5743(2) 0.18928(9) 0.0403(5) Uani 1 1 d . . . . .
H7 H -0.1549 0.6640 0.1903 0.048 Uiso 1 1 calc R . . . .
C8 C -0.07310(14) 0.53609(19) 0.17574(9) 0.0380(5) Uani 1 1 d . . . . .
H8 H -0.0318(18) 0.597(3) 0.1683(11) 0.064(8) Uiso 1 1 d . . . . .
C10 C -0.07331(13) 0.1768(2) 0.17813(9) 0.0330(4) Uani 1 1 d . . . . .
H10 H -0.0723(19) 0.121(3) 0.1996(12) 0.073(10) Uiso 1 1 d . . . . .
C11 C 0.01182(12) 0.20084(18) 0.16610(8) 0.0330(4) Uani 1 1 d . . . . .
C12 C 0.02395(13) 0.35315(19) 0.16510(9) 0.0364(5) Uani 1 1 d . . . . .
C13 C 0.09617(14) 0.39701(19) 0.21065(9) 0.0368(5) Uani 1 1 d . . . . .
C14 C 0.03507(13) 0.4022(2) 0.11324(9) 0.0364(5) Uani 1 1 d . . . . .
C15 C 0.06726(12) 0.10843(18) 0.15920(8) 0.0319(4) Uani 1 1 d . . . . .
C16 C 0.15054(12) 0.14932(19) 0.14987(9) 0.0336(4) Uani 1 1 d . . . . .
C17 C 0.27923(13) 0.0862(2) 0.13036(10) 0.0416(5) Uani 1 1 d . . . . .
H17A H 0.3149 0.1218 0.1636 0.050 Uiso 1 1 calc R . . . .
H17B H 0.2729 0.1531 0.1027 0.050 Uiso 1 1 calc R . . . .
C18 C 0.31954(16) -0.0347(2) 0.11473(12) 0.0552(7) Uani 1 1 d . . . . .
H18A H 0.2851 -0.0669 0.0810 0.083 Uiso 1 1 calc GR . . . .
H18B H 0.3237 -0.1015 0.1417 0.083 Uiso 1 1 calc GR . . . .
H18C H 0.3759 -0.0137 0.1114 0.083 Uiso 1 1 calc GR . . . .
C19 C 0.04719(13) -0.03719(18) 0.16286(9) 0.0331(4) Uani 1 1 d . . . . .
H19A H 0.1000 -0.0871 0.1683 0.040 Uiso 1 1 calc R . . . .
H19B H 0.0254 -0.0509 0.1941 0.040 Uiso 1 1 calc R . . . .
C20 C -0.01735(13) -0.09128(17) 0.11395(8) 0.0324(4) Uani 1 1 d . . . . .
C21 C -0.09786(14) -0.13107(19) 0.11720(9) 0.0393(5) Uani 1 1 d . . . . .
H21 H -0.1121 -0.1235 0.1497 0.047 Uiso 1 1 calc R . . . .
C22 C -0.15755(15) -0.1818(2) 0.07322(11) 0.0489(6) Uani 1 1 d . . . . .
H22 H -0.2114 -0.2072 0.0763 0.059 Uiso 1 1 calc R . . . .
C23 C -0.13738(17) -0.1947(2) 0.02503(11) 0.0541(7) Uani 1 1 d . . . . .
H23 H -0.1772 -0.2294 -0.0046 0.065 Uiso 1 1 calc R . . . .
C24 C -0.05741(18) -0.1558(3) 0.02093(10) 0.0556(7) Uani 1 1 d . . . . .
H24 H -0.0435 -0.1645 -0.0117 0.067 Uiso 1 1 calc R . . . .
C25 C 0.00254(15) -0.1038(2) 0.06496(10) 0.0456(5) Uani 1 1 d . . . . .
H25 H 0.0560 -0.0773 0.0616 0.055 Uiso 1 1 calc R . . . .
C9 C -0.0897(3) 0.3063(4) 0.2010(2) 0.0257(11) Uani 0.514(9) 1 d . . P A 1
H9 H -0.0558 0.3078 0.2385 0.031 Uiso 0.514(9) 1 calc R . P A 1
O3 O 0.34651(10) 0.37995(14) 0.10285(8) 0.0502(4) Uani 1 1 d . . . . .
O4 O 0.31769(8) 0.59302(13) 0.11414(6) 0.0353(3) Uani 1 1 d . . . . .
N4 N 0.56836(10) 0.27039(15) 0.05837(7) 0.0330(4) Uani 1 1 d . . . . .
N5 N 0.36346(13) 0.21894(19) 0.00123(8) 0.0497(5) Uani 1 1 d . . . . .
N6 N 0.50048(13) 0.1820(2) 0.16725(8) 0.0493(5) Uani 1 1 d . . . . .
C26 C 0.79935(13) 0.1962(2) 0.02230(8) 0.0386(5) Uani 1 1 d . . . . .
H26 H 0.8148 0.1102 0.0162 0.046 Uiso 1 1 calc R . . . .
C27 C 0.84878(13) 0.3012(2) 0.01301(9) 0.0407(5) Uani 1 1 d . . . . .
H27 H 0.8973 0.2851 0.0010 0.049 Uiso 1 1 calc R . . . .
C28 C 0.82646(13) 0.4292(2) 0.02154(8) 0.0379(5) Uani 1 1 d . . . . .
H28 H 0.8591 0.4994 0.0145 0.045 Uiso 1 1 calc R . . . .
C29 C 0.75518(12) 0.4531(2) 0.04061(8) 0.0335(4) Uani 1 1 d . . . . .
H29 H 0.7403 0.5394 0.0466 0.040 Uiso 1 1 calc R . . . .
C30 C 0.70617(12) 0.34897(18) 0.05068(8) 0.0295(4) Uani 1 1 d . . . . .
C31 C 0.72693(13) 0.21842(19) 0.04068(8) 0.0324(4) Uani 1 1 d . . . . .
C32 C 0.67031(14) 0.1118(2) 0.04820(9) 0.0383(5) Uani 1 1 d . . . . .
H32 H 0.6878 0.0244 0.0475 0.046 Uiso 1 1 calc R . . . .
C33 C 0.59416(14) 0.13854(19) 0.05607(9) 0.0377(5) Uani 1 1 d . . . . .
H33 H 0.5481(15) 0.070(2) 0.0593(9) 0.048(7) Uiso 1 1 d . . . . .
C34 C 0.63580(12) 0.36721(18) 0.07840(8) 0.0324(4) Uani 1 1 d . . . . .
H34 H 0.6597 0.3523 0.1169 0.039 Uiso 1 1 calc R . . . .
C35 C 0.58630(12) 0.49515(18) 0.07093(8) 0.0305(4) Uani 1 1 d . . . . .
H35A H 0.6154 0.5611 0.0965 0.037 Uiso 1 1 calc R . . . .
H35B H 0.5788 0.5293 0.0349 0.037 Uiso 1 1 calc R . . . .
C36 C 0.50139(12) 0.45833(18) 0.08062(8) 0.0300(4) Uani 1 1 d . . . . .
C37 C 0.49399(12) 0.30560(18) 0.07678(8) 0.0310(4) Uani 1 1 d . . . . .
C38 C 0.49500(13) 0.24085(19) 0.12891(9) 0.0343(4) Uani 1 1 d . . . . .
C39 C 0.41682(13) 0.25898(19) 0.03558(9) 0.0353(4) Uani 1 1 d . . . . .
C40 C 0.44462(12) 0.54439(18) 0.08992(8) 0.0311(4) Uani 1 1 d . . . . .
C41 C 0.36523(12) 0.49537(19) 0.10254(9) 0.0352(4) Uani 1 1 d . . . . .
C42 C 0.23841(13) 0.5510(2) 0.12611(10) 0.0395(5) Uani 1 1 d . . . . .
H42A H 0.2509 0.4953 0.1578 0.047 Uiso 1 1 calc R . . . .
H42B H 0.2033 0.5012 0.0963 0.047 Uiso 1 1 calc R . . . .
C43 C 0.19223(14) 0.6736(2) 0.13554(9) 0.0404(5) Uani 1 1 d . . . . .
H43A H 0.1788 0.7267 0.1036 0.061 Uiso 1 1 calc GR . . . .
H43B H 0.2281 0.7231 0.1646 0.061 Uiso 1 1 calc GR . . . .
H43C H 0.1402 0.6495 0.1445 0.061 Uiso 1 1 calc GR . . . .
C44 C 0.45962(12) 0.69166(18) 0.08698(8) 0.0326(4) Uani 1 1 d . . . . .
H44A H 0.4795 0.7093 0.0553 0.039 Uiso 1 1 calc R . . . .
H44B H 0.4052 0.7366 0.0824 0.039 Uiso 1 1 calc R . . . .
C45 C 0.52332(13) 0.75071(18) 0.13516(8) 0.0321(4) Uani 1 1 d . . . . .
C46 C 0.59256(14) 0.8228(2) 0.12812(9) 0.0387(5) Uani 1 1 d . . . . .
H46 H 0.5998 0.8326 0.0938 0.046 Uiso 1 1 calc R . . . .
C47 C 0.65101(16) 0.8804(2) 0.17093(10) 0.0494(6) Uani 1 1 d . . . . .
H47 H 0.6971 0.9280 0.1653 0.059 Uiso 1 1 calc R . . . .
C48 C 0.64076(18) 0.8671(3) 0.22187(10) 0.0544(6) Uani 1 1 d . . . . .
H48 H 0.6796 0.9062 0.2508 0.065 Uiso 1 1 calc R . . . .
C49 C 0.57291(18) 0.7960(3) 0.22974(10) 0.0565(7) Uani 1 1 d . . . . .
H49 H 0.5661 0.7866 0.2642 0.068 Uiso 1 1 calc R . . . .
C50 C 0.51433(15) 0.7379(2) 0.18686(9) 0.0451(5) Uani 1 1 d . . . . .
H50 H 0.4686 0.6899 0.1928 0.054 Uiso 1 1 calc R . . . .
C9A C -0.1172(3) 0.3096(4) 0.1682(3) 0.0307(14) Uani 0.486(9) 1 d . . P A 2
H9A H -0.1492 0.3110 0.1303 0.037 Uiso 0.486(9) 1 calc R . P A 2


_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 C16 1.211(2) . ?
O2 C16 1.331(2) . ?
O2 C17 1.465(2) . ?
N1 C8 1.391(3) . ?
N1 C12 1.449(3) . ?
N1 C9 1.386(4) . ?
N1 C9A 1.344(4) . ?
N2 C13 1.138(3) . ?
N3 C14 1.135(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.378(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.402(3) . ?
C5 C9 1.537(4) . ?
C5 C9A 1.540(5) . ?
C6 C7 1.454(3) . ?
C7 C8 1.322(3) . ?
C10 C11 1.507(3) . ?
C10 C9 1.490(4) . ?
C10 C9A 1.510(4) . ?
C11 C12 1.555(3) . ?
C11 C15 1.339(3) . ?
C12 C13 1.491(3) . ?
C12 C14 1.482(3) . ?
C15 C16 1.486(3) . ?
C15 C19 1.517(3) . ?
C17 C18 1.490(3) . ?
C19 C20 1.514(3) . ?
C20 C21 1.385(3) . ?
C20 C25 1.390(3) . ?
C21 C22 1.382(3) . ?
C22 C23 1.372(4) . ?
C23 C24 1.381(4) . ?
C24 C25 1.390(3) . ?
O3 C41 1.207(2) . ?
O4 C41 1.333(2) . ?
O4 C42 1.457(2) . ?
N4 C33 1.404(2) . ?
N4 C34 1.456(2) . ?
N4 C37 1.447(3) . ?
N5 C39 1.138(3) . ?
N6 C38 1.139(3) . ?
C26 C27 1.387(3) . ?
C26 C31 1.391(3) . ?
C27 C28 1.377(3) . ?
C28 C29 1.387(3) . ?
C29 C30 1.382(3) . ?
C30 C31 1.403(3) . ?
C30 C34 1.505(3) . ?
C31 C32 1.460(3) . ?
C32 C33 1.326(3) . ?
C34 C35 1.507(3) . ?
C35 C36 1.504(3) . ?
C36 C37 1.551(3) . ?
C36 C40 1.331(3) . ?
C37 C38 1.493(3) . ?
C37 C39 1.488(3) . ?
C40 C41 1.489(3) . ?
C40 C44 1.515(3) . ?
C42 C43 1.500(3) . ?
C44 C45 1.515(3) . ?
C45 C46 1.387(3) . ?
C45 C50 1.386(3) . ?
C46 C47 1.381(3) . ?
C47 C48 1.374(4) . ?
C48 C49 1.370(4) . ?
C49 C50 1.385(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
C16 O2 C17 114.45(15) . . ?
C8 N1 C12 122.23(17) . . ?
C9 N1 C8 123.6(2) . . ?
C9 N1 C12 109.2(2) . . ?
C9A N1 C8 122.0(2) . . ?
C9A N1 C12 114.1(2) . . ?
C2 C1 C6 120.6(2) . . ?
C3 C2 C1 120.4(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 119.9(2) . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 C9 119.7(2) . . ?
C4 C5 C9A 122.3(2) . . ?
C6 C5 C9 117.2(2) . . ?
C6 C5 C9A 114.9(2) . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 122.57(19) . . ?
C5 C6 C7 118.83(19) . . ?
C8 C7 C6 120.96(19) . . ?
C7 C8 N1 119.3(2) . . ?
C11 C10 C9A 103.6(2) . . ?
C9 C10 C11 101.9(2) . . ?
C10 C11 C12 106.83(16) . . ?
C15 C11 C10 126.37(18) . . ?
C15 C11 C12 126.77(18) . . ?
N1 C12 C11 102.32(15) . . ?
N1 C12 C13 108.50(19) . . ?
N1 C12 C14 110.56(18) . . ?
C13 C12 C11 110.98(17) . . ?
C14 C12 C11 113.10(18) . . ?
C14 C12 C13 110.99(17) . . ?
N2 C13 C12 170.7(2) . . ?
N3 C14 C12 175.9(2) . . ?
C11 C15 C16 119.52(17) . . ?
C11 C15 C19 120.58(18) . . ?
C16 C15 C19 119.86(17) . . ?
O1 C16 O2 123.05(19) . . ?
O1 C16 C15 123.49(18) . . ?
O2 C16 C15 113.46(16) . . ?
O2 C17 C18 107.98(17) . . ?
C20 C19 C15 114.26(16) . . ?
C21 C20 C19 120.50(19) . . ?
C21 C20 C25 118.2(2) . . ?
C25 C20 C19 121.28(19) . . ?
C22 C21 C20 121.5(2) . . ?
C23 C22 C21 120.0(2) . . ?
C22 C23 C24 119.4(2) . . ?
C23 C24 C25 120.8(2) . . ?
C20 C25 C24 120.1(2) . . ?
N1 C9 C5 109.9(3) . . ?
N1 C9 C10 106.2(3) . . ?
C10 C9 C5 119.0(3) . . ?
C41 O4 C42 114.93(15) . . ?
C33 N4 C34 116.84(16) . . ?
C33 N4 C37 121.95(16) . . ?
C37 N4 C34 109.04(15) . . ?
C27 C26 C31 120.6(2) . . ?
C28 C27 C26 120.4(2) . . ?
C27 C28 C29 119.8(2) . . ?
C30 C29 C28 120.24(19) . . ?
C29 C30 C31 120.42(18) . . ?
C29 C30 C34 122.49(17) . . ?
C31 C30 C34 116.71(17) . . ?
C26 C31 C30 118.55(19) . . ?
C26 C31 C32 122.53(18) . . ?
C30 C31 C32 118.89(18) . . ?
C33 C32 C31 120.53(18) . . ?
C32 C33 N4 119.89(19) . . ?
N4 C34 C30 109.70(16) . . ?
N4 C34 C35 102.10(15) . . ?
C30 C34 C35 119.08(17) . . ?
C36 C35 C34 104.03(15) . . ?
C35 C36 C37 107.13(16) . . ?
C40 C36 C35 124.70(17) . . ?
C40 C36 C37 128.17(18) . . ?
N4 C37 C36 102.09(15) . . ?
N4 C37 C38 111.93(16) . . ?
N4 C37 C39 107.43(17) . . ?
C38 C37 C36 113.40(17) . . ?
C39 C37 C36 113.43(16) . . ?
C39 C37 C38 108.36(16) . . ?
N6 C38 C37 173.3(2) . . ?
N5 C39 C37 173.0(2) . . ?
C36 C40 C41 119.68(17) . . ?
C36 C40 C44 120.51(18) . . ?
C41 C40 C44 119.81(17) . . ?
O3 C41 O4 123.78(19) . . ?
O3 C41 C40 123.75(18) . . ?
O4 C41 C40 112.47(16) . . ?
O4 C42 C43 107.18(16) . . ?
C45 C44 C40 115.48(17) . . ?
C46 C45 C44 119.89(18) . . ?
C50 C45 C44 122.30(19) . . ?
C50 C45 C46 117.8(2) . . ?
C47 C46 C45 121.6(2) . . ?
C48 C47 C46 119.8(2) . . ?
C49 C48 C47 119.6(2) . . ?
C48 C49 C50 120.7(2) . . ?
C49 C50 C45 120.6(2) . . ?
N1 C9A C5 112.0(3) . . ?
N1 C9A C10 107.3(3) . . ?
C10 C9A C5 117.5(3) . . ?

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 C2 C3 C4 -0.8(3) . . . . ?
C1 C6 C7 C8 179.7(2) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -179.7(2) . . . . ?
C2 C3 C4 C5 0.3(3) . . . . ?
C3 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C9 161.6(3) . . . . ?
C3 C4 C5 C9A -161.0(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 C7 179.2(2) . . . . ?
C4 C5 C9 N1 164.7(3) . . . . ?
C4 C5 C9 C10 42.0(5) . . . . ?
C4 C5 C9A N1 -161.0(3) . . . . ?
C4 C5 C9A C10 -36.1(5) . . . . ?
C5 C6 C7 C8 -0.2(3) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C6 C5 C9 N1 -33.6(4) . . . . ?
C6 C5 C9 C10 -156.3(3) . . . . ?
C6 C5 C9A N1 36.6(5) . . . . ?
C6 C5 C9A C10 161.5(3) . . . . ?
C6 C7 C8 N1 0.3(4) . . . . ?
C8 N1 C12 C11 -179.4(2) . . . . ?
C8 N1 C12 C13 63.2(3) . . . . ?
C8 N1 C12 C14 -58.7(3) . . . . ?
C8 N1 C9 C5 36.2(5) . . . . ?
C8 N1 C9 C10 166.2(2) . . . . ?
C8 N1 C9A C5 -39.5(6) . . . . ?
C8 N1 C9A C10 -169.9(3) . . . . ?
C10 C11 C12 N1 -2.5(2) . . . . ?
C10 C11 C12 C13 113.07(19) . . . . ?
C10 C11 C12 C14 -121.44(19) . . . . ?
C10 C11 C15 C16 -177.4(2) . . . . ?
C10 C11 C15 C19 0.4(3) . . . . ?
C11 C10 C9 N1 34.2(4) . . . . ?
C11 C10 C9 C5 158.7(3) . . . . ?
C11 C10 C9A N1 -23.8(4) . . . . ?
C11 C10 C9A C5 -151.0(3) . . . . ?
C11 C15 C16 O1 8.2(3) . . . . ?
C11 C15 C16 O2 -172.32(19) . . . . ?
C11 C15 C19 C20 76.4(3) . . . . ?
C12 N1 C8 C7 -173.3(2) . . . . ?
C12 N1 C9 C5 -168.5(2) . . . . ?
C12 N1 C9 C10 -38.5(4) . . . . ?
C12 N1 C9A C5 154.7(3) . . . . ?
C12 N1 C9A C10 24.4(5) . . . . ?
C12 C11 C15 C16 0.5(3) . . . . ?
C12 C11 C15 C19 178.3(2) . . . . ?
C15 C11 C12 N1 179.3(2) . . . . ?
C15 C11 C12 C13 -65.1(3) . . . . ?
C15 C11 C12 C14 60.4(3) . . . . ?
C15 C19 C20 C21 -112.2(2) . . . . ?
C15 C19 C20 C25 68.5(2) . . . . ?
C16 O2 C17 C18 -178.2(2) . . . . ?
C16 C15 C19 C20 -105.9(2) . . . . ?
C17 O2 C16 O1 2.3(3) . . . . ?
C17 O2 C16 C15 -177.20(18) . . . . ?
C19 C15 C16 O1 -169.6(2) . . . . ?
C19 C15 C16 O2 9.9(3) . . . . ?
C19 C20 C21 C22 -179.44(19) . . . . ?
C19 C20 C25 C24 178.9(2) . . . . ?
C20 C21 C22 C23 0.5(3) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
C22 C23 C24 C25 -0.1(4) . . . . ?
C23 C24 C25 C20 0.5(4) . . . . ?
C25 C20 C21 C22 -0.1(3) . . . . ?
C9 N1 C8 C7 -21.1(4) . . . . ?
C9 N1 C12 C11 24.9(3) . . . . ?
C9 N1 C12 C13 -92.5(3) . . . . ?
C9 N1 C12 C14 145.6(3) . . . . ?
C9 N1 C9A C5 65.0(5) . . . . ?
C9 N1 C9A C10 -65.4(4) . . . . ?
C9 C5 C6 C1 -162.3(3) . . . . ?
C9 C5 C6 C7 17.6(4) . . . . ?
C9 C5 C9A N1 -65.5(5) . . . . ?
C9 C5 C9A C10 59.4(4) . . . . ?
C9 C10 C11 C12 -18.3(3) . . . . ?
C9 C10 C11 C15 159.9(3) . . . . ?
C9 C10 C9A N1 67.0(4) . . . . ?
C9 C10 C9A C5 -60.2(5) . . . . ?
N4 C34 C35 C36 33.7(2) . . . . ?
C26 C27 C28 C29 1.4(3) . . . . ?
C26 C31 C32 C33 -167.4(2) . . . . ?
C27 C26 C31 C30 -1.4(3) . . . . ?
C27 C26 C31 C32 176.5(2) . . . . ?
C27 C28 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C31 -1.3(3) . . . . ?
C28 C29 C30 C34 171.36(19) . . . . ?
C29 C30 C31 C26 2.2(3) . . . . ?
C29 C30 C31 C32 -175.73(19) . . . . ?
C29 C30 C34 N4 148.48(18) . . . . ?
C29 C30 C34 C35 31.5(3) . . . . ?
C30 C31 C32 C33 10.5(3) . . . . ?
C30 C34 C35 C36 154.65(17) . . . . ?
C31 C26 C27 C28 -0.4(3) . . . . ?
C31 C30 C34 N4 -38.6(2) . . . . ?
C31 C30 C34 C35 -155.56(18) . . . . ?
C31 C32 C33 N4 -1.4(3) . . . . ?
C33 N4 C34 C30 48.3(2) . . . . ?
C33 N4 C34 C35 175.52(18) . . . . ?
C33 N4 C37 C36 171.23(18) . . . . ?
C33 N4 C37 C38 49.6(3) . . . . ?
C33 N4 C37 C39 -69.2(2) . . . . ?
C34 N4 C33 C32 -29.8(3) . . . . ?
C34 N4 C37 C36 30.1(2) . . . . ?
C34 N4 C37 C38 -91.47(19) . . . . ?
C34 N4 C37 C39 149.70(16) . . . . ?
C34 C30 C31 C26 -170.86(18) . . . . ?
C34 C30 C31 C32 11.2(3) . . . . ?
C34 C35 C36 C37 -16.4(2) . . . . ?
C34 C35 C36 C40 164.4(2) . . . . ?
C35 C36 C37 N4 -7.4(2) . . . . ?
C35 C36 C37 C38 113.23(19) . . . . ?
C35 C36 C37 C39 -122.61(18) . . . . ?
C35 C36 C40 C41 -175.95(18) . . . . ?
C35 C36 C40 C44 4.9(3) . . . . ?
C36 C40 C41 O3 -3.2(3) . . . . ?
C36 C40 C41 O4 176.02(18) . . . . ?
C36 C40 C44 C45 -77.8(3) . . . . ?
C37 N4 C33 C32 -168.1(2) . . . . ?
C37 N4 C34 C30 -168.36(16) . . . . ?
C37 N4 C34 C35 -41.2(2) . . . . ?
C37 C36 C40 C41 5.0(3) . . . . ?
C37 C36 C40 C44 -174.13(19) . . . . ?
C40 C36 C37 N4 171.8(2) . . . . ?
C40 C36 C37 C38 -67.6(3) . . . . ?
C40 C36 C37 C39 56.6(3) . . . . ?
C40 C44 C45 C46 125.5(2) . . . . ?
C40 C44 C45 C50 -55.9(3) . . . . ?
C41 O4 C42 C43 -177.45(18) . . . . ?
C41 C40 C44 C45 103.1(2) . . . . ?
C42 O4 C41 O3 -1.6(3) . . . . ?
C42 O4 C41 C40 179.16(17) . . . . ?
C44 C40 C41 O3 176.0(2) . . . . ?
C44 C40 C41 O4 -4.8(3) . . . . ?
C44 C45 C46 C47 178.7(2) . . . . ?
C44 C45 C50 C49 -178.5(2) . . . . ?
C45 C46 C47 C48 -0.3(4) . . . . ?
C46 C45 C50 C49 0.1(3) . . . . ?
C46 C47 C48 C49 0.5(4) . . . . ?
C47 C48 C49 C50 -0.3(4) . . . . ?
C48 C49 C50 C45 0.0(4) . . . . ?
C50 C45 C46 C47 0.0(3) . . . . ?
C9A N1 C8 C7 22.1(5) . . . . ?
C9A N1 C12 C11 -13.7(4) . . . . ?
C9A N1 C12 C13 -131.1(4) . . . . ?
C9A N1 C12 C14 107.0(4) . . . . ?
C9A N1 C9 C5 -63.5(4) . . . . ?
C9A N1 C9 C10 66.5(4) . . . . ?
C9A C5 C6 C1 162.1(3) . . . . ?
C9A C5 C6 C7 -18.0(4) . . . . ?
C9A C5 C9 N1 60.4(4) . . . . ?
C9A C5 C9 C10 -62.3(4) . . . . ?
C9A C10 C11 C12 15.3(3) . . . . ?
C9A C10 C11 C15 -166.5(3) . . . . ?
C9A C10 C9 N1 -62.6(4) . . . . ?
C9A C10 C9 C5 61.9(5) . . . . ?

####################################################################### 
# 
# 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_sa4018a
_database_code_depnum_ccdc_archive 'CCDC 1455370'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H17 N3 O2'
_chemical_formula_sum            'C19 H17 N3 O2'
_chemical_formula_weight         319.35
_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      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                   8.427(5)
_cell_length_b                   8.87(5)
_cell_length_c                   11.531(7)
_cell_angle_alpha                83.90(3)
_cell_angle_beta                 89.32(3)
_cell_angle_gamma                71.399(19)
_cell_volume                     812(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2768
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4667
_cell_measurement_theta_min      1.7766
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4197
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6873
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.452
_diffrn_reflns_theta_min         2.858
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 40.1167
	          2theta: -20.2741
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 15.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.1167
	          2theta: -20.2741
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             3616
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0163
_diffrn_orient_matrix_UB_12      -0.1132
_diffrn_orient_matrix_UB_13      0.0510
_diffrn_orient_matrix_UB_21      -0.0207
_diffrn_orient_matrix_UB_22      -0.0077
_diffrn_orient_matrix_UB_23      -0.1177
_diffrn_orient_matrix_UB_31      0.0856
_diffrn_orient_matrix_UB_32      -0.0165
_diffrn_orient_matrix_UB_33      -0.0043
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3003
_reflns_number_total             3614
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3614
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1078
_refine_ls_R_factor_gt           0.0943
_refine_ls_restrained_S_all      1.112
_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)+(0.1504P)²+0.3504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2530
_refine_ls_wR_factor_ref         0.2690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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 0.5890(3) 0.6364(2) 0.6824(2) 0.0485(6) Uani 1 1 d . . . . .
O2 O 0.6000(3) 0.5314(2) 0.87006(18) 0.0413(5) Uani 1 1 d . . . . .
N1 N 1.0236(3) 0.1011(2) 0.62626(19) 0.0294(5) Uani 1 1 d . . . . .
N2 N 1.1539(3) -0.0380(3) 0.6337(2) 0.0346(5) Uani 1 1 d . . . . .
N3 N 0.8528(4) -0.0696(3) 0.8654(3) 0.0599(8) Uani 1 1 d . . . . .
C1 C 1.2694(3) -0.0404(3) 0.5565(3) 0.0374(6) Uani 1 1 d . . . . .
H1 H 1.3617 -0.1327 0.5589 0.045 Uiso 1 1 calc R . . . .
C2 C 1.2650(3) 0.0866(3) 0.4697(2) 0.0375(6) Uani 1 1 d . . . . .
H2 H 1.3516 0.0761 0.4173 0.045 Uiso 1 1 calc R . . . .
C3 C 1.1329(3) 0.2240(3) 0.4639(2) 0.0350(6) Uani 1 1 d . . . . .
H3 H 1.1268 0.3086 0.4072 0.042 Uiso 1 1 calc R . . . .
C4 C 1.0050(3) 0.2354(3) 0.5461(2) 0.0308(6) Uani 1 1 d . . . . .
C5 C 0.8559(3) 0.3506(3) 0.5710(2) 0.0313(6) Uani 1 1 d . . . . .
H5 H 0.8117 0.4524 0.5313 0.038 Uiso 1 1 calc R . . . .
C6 C 0.7835(3) 0.2868(3) 0.6662(2) 0.0296(5) Uani 1 1 d . . . . .
C7 C 0.8900(3) 0.1313(3) 0.6991(2) 0.0301(5) Uani 1 1 d . . . . .
C8 C 0.8737(4) 0.0173(3) 0.7904(3) 0.0387(6) Uani 1 1 d . . . . .
C9 C 0.6215(3) 0.3566(3) 0.7259(2) 0.0301(6) Uani 1 1 d . . . . .
H9 H 0.6237 0.2893 0.7994 0.036 Uiso 1 1 calc R . . . .
C10 C 0.4696(3) 0.3575(4) 0.6521(2) 0.0383(6) Uani 1 1 d . . . . .
H10A H 0.4448 0.4462 0.5909 0.046 Uiso 1 1 calc R . . . .
H10B H 0.4974 0.2591 0.6152 0.046 Uiso 1 1 calc R . . . .
C11 C 0.3159(3) 0.3726(3) 0.7253(2) 0.0330(6) Uani 1 1 d . . . . .
C12 C 0.2905(3) 0.2341(3) 0.7799(2) 0.0358(6) Uani 1 1 d . . . . .
H12 H 0.3649 0.1344 0.7678 0.043 Uiso 1 1 calc R . . . .
C13 C 0.1556(4) 0.2436(4) 0.8519(3) 0.0407(7) Uani 1 1 d . . . . .
H13 H 0.1402 0.1503 0.8875 0.049 Uiso 1 1 calc R . . . .
C14 C 0.0443(3) 0.3900(4) 0.8712(3) 0.0429(7) Uani 1 1 d . . . . .
H14 H -0.0462 0.3961 0.9195 0.051 Uiso 1 1 calc R . . . .
C15 C 0.0684(4) 0.5277(4) 0.8180(3) 0.0437(7) Uani 1 1 d . . . . .
H15 H -0.0059 0.6270 0.8311 0.052 Uiso 1 1 calc R . . . .
C16 C 0.2034(3) 0.5193(3) 0.7446(2) 0.0371(6) Uani 1 1 d . . . . .
H16 H 0.2176 0.6129 0.7085 0.045 Uiso 1 1 calc R . . . .
C17 C 0.6011(3) 0.5251(3) 0.7550(2) 0.0343(6) Uani 1 1 d . . . . .
C18 C 0.5829(4) 0.6833(4) 0.9130(3) 0.0541(9) Uani 1 1 d . . . . .
H18A H 0.6424 0.7408 0.8627 0.065 Uiso 1 1 calc R . . . .
H18B H 0.6330 0.6643 0.9907 0.065 Uiso 1 1 calc R . . . .
C19 C 0.4027(5) 0.7835(4) 0.9170(3) 0.0556(9) Uani 1 1 d . . . . .
H19A H 0.3547 0.8082 0.8395 0.083 Uiso 1 1 calc GR . . . .
H19B H 0.3950 0.8811 0.9492 0.083 Uiso 1 1 calc GR . . . .
H19C H 0.3429 0.7256 0.9650 0.083 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C17 1.203(5) . ?
O2 C17 1.333(4) . ?
O2 C18 1.448(8) . ?
N1 N2 1.360(5) . ?
N1 C4 1.396(6) . ?
N1 C7 1.370(3) . ?
N2 C1 1.308(4) . ?
N3 C8 1.147(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.417(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.359(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.413(4) . ?
C4 C5 1.392(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(4) . ?
C6 C7 1.399(7) . ?
C6 C9 1.500(4) . ?
C7 C8 1.417(5) . ?
C9 H9 0.9800 . ?
C9 C10 1.544(4) . ?
C9 C17 1.522(9) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.515(4) . ?
C11 C12 1.396(7) . ?
C11 C16 1.383(7) . ?
C12 H12 0.9300 . ?
C12 C13 1.386(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.380(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.397(4) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.498(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C17 O2 C18 118.4(3) . . ?
N2 N1 C4 126.2(3) . . ?
N2 N1 C7 124.5(2) . . ?
C7 N1 C4 109.2(2) . . ?
C1 N2 N1 114.4(3) . . ?
N2 C1 H1 117.5 . . ?
N2 C1 C2 125.1(3) . . ?
C2 C1 H1 117.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.5(3) . . ?
C4 C3 H3 120.8 . . ?
N1 C4 C3 116.5(2) . . ?
C5 C4 N1 107.0(3) . . ?
C5 C4 C3 136.5(3) . . ?
C4 C5 H5 125.8 . . ?
C4 C5 C6 108.4(3) . . ?
C6 C5 H5 125.8 . . ?
C5 C6 C9 130.7(3) . . ?
C7 C6 C5 107.2(3) . . ?
C7 C6 C9 122.1(2) . . ?
N1 C7 C6 108.2(2) . . ?
N1 C7 C8 122.5(3) . . ?
C6 C7 C8 129.3(3) . . ?
N3 C8 C7 176.5(3) . . ?
C6 C9 H9 107.9 . . ?
C6 C9 C10 111.8(2) . . ?
C6 C9 C17 111.3(2) . . ?
C10 C9 H9 107.9 . . ?
C17 C9 H9 107.9 . . ?
C17 C9 C10 110.0(2) . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 C9 111.9(2) . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C12 C11 C10 119.1(3) . . ?
C16 C11 C10 122.3(3) . . ?
C16 C11 C12 118.5(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.3(4) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 120.3(3) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
O1 C17 O2 125.3(3) . . ?
O1 C17 C9 123.5(4) . . ?
O2 C17 C9 111.2(2) . . ?
O2 C18 H18A 109.4 . . ?
O2 C18 H18B 109.4 . . ?
O2 C18 C19 111.4(3) . . ?
H18A C18 H18B 108.0 . . ?
C19 C18 H18A 109.4 . . ?
C19 C18 H18B 109.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N1 N2 C1 C2 -0.7(4) . . . . ?
N1 C4 C5 C6 0.0(3) . . . . ?
N2 N1 C4 C3 1.1(4) . . . . ?
N2 N1 C4 C5 -179.0(2) . . . . ?
N2 N1 C7 C6 179.0(2) . . . . ?
N2 N1 C7 C8 -0.7(4) . . . . ?
N2 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 N1 -1.3(4) . . . . ?
C2 C3 C4 C5 178.8(3) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C4 N1 N2 C1 -0.1(3) . . . . ?
C4 N1 C7 C6 -0.1(3) . . . . ?
C4 N1 C7 C8 -179.8(2) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C6 C9 -177.7(2) . . . . ?
C5 C6 C7 N1 0.1(3) . . . . ?
C5 C6 C7 C8 179.7(3) . . . . ?
C5 C6 C9 C10 74.3(4) . . . . ?
C5 C6 C9 C17 -49.1(4) . . . . ?
C6 C9 C10 C11 160.4(2) . . . . ?
C6 C9 C17 O1 64.3(3) . . . . ?
C6 C9 C17 O2 -115.2(2) . . . . ?
C7 N1 N2 C1 -179.0(2) . . . . ?
C7 N1 C4 C3 -179.9(2) . . . . ?
C7 N1 C4 C5 0.0(3) . . . . ?
C7 C6 C9 C10 -103.0(4) . . . . ?
C7 C6 C9 C17 133.6(3) . . . . ?
C9 C6 C7 N1 178.0(2) . . . . ?
C9 C6 C7 C8 -2.4(4) . . . . ?
C9 C10 C11 C12 -88.1(3) . . . . ?
C9 C10 C11 C16 88.8(3) . . . . ?
C10 C9 C17 O1 -60.2(3) . . . . ?
C10 C9 C17 O2 120.3(2) . . . . ?
C10 C11 C12 C13 177.0(2) . . . . ?
C10 C11 C16 C15 -176.4(2) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C12 C11 C16 C15 0.5(4) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C14 C15 C16 C11 -0.7(4) . . . . ?
C16 C11 C12 C13 -0.1(4) . . . . ?
C17 O2 C18 C19 84.8(3) . . . . ?
C17 C9 C10 C11 -75.4(3) . . . . ?
C18 O2 C17 O1 0.0(4) . . . . ?
C18 O2 C17 C9 179.5(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_sa4017
_database_code_depnum_ccdc_archive 'CCDC 1455373'
_audit_update_record             
;
2016-02-24 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2015-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H18 Br N3 O2'
_chemical_formula_sum            'C23 H18 Br N3 O2'
_chemical_formula_weight         448.31
_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'
Br Br -0.2901 2.4595 '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                   9.234(3)
_cell_length_b                   10.079(3)
_cell_length_c                   11.771(4)
_cell_angle_alpha                74.328(11)
_cell_angle_beta                 87.518(14)
_cell_angle_gamma                72.598(10)
_cell_volume                     1005.7(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      2.4367
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.068
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12571
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_min         1.798
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 270.0000
	             XTD: 40.0919
	          2theta: -19.8975
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 40.0919
	          2theta: -19.8975
scan:
	Number of images: 344
	           Slice: -110.0000 - 62.0000
	     Image width: 0.5000
	        Exp time: 8.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 40.0919
	          2theta: -19.8975
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             4584
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0121
_diffrn_orient_matrix_UB_12      -0.1129
_diffrn_orient_matrix_UB_13      -0.0036
_diffrn_orient_matrix_UB_21      -0.0231
_diffrn_orient_matrix_UB_22      0.0332
_diffrn_orient_matrix_UB_23      -0.1001
_diffrn_orient_matrix_UB_31      0.0878
_diffrn_orient_matrix_UB_32      0.0056
_diffrn_orient_matrix_UB_33      0.0073
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4230
_reflns_number_total             4584
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.701
_refine_diff_density_min         -0.738
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.8188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_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, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C19(H19), C20(H20), C22(H22),
 C23(H23)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
Br1 Br 0.32288(3) 0.88785(3) 1.02594(2) 0.04644(11) Uani 1 1 d . . . . .
O1 O 0.88625(19) 0.56273(18) 0.63074(15) 0.0352(4) Uani 1 1 d . . . . .
O2 O 0.92319(17) 0.39438(17) 0.80469(14) 0.0315(3) Uani 1 1 d . . . . .
N1 N 0.63544(19) 0.05917(19) 0.52057(16) 0.0250(4) Uani 1 1 d . . . . .
N2 N 0.69610(18) 0.16165(17) 0.53691(15) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.4009(2) 0.2249(2) 0.7285(2) 0.0388(5) Uani 1 1 d . . . . .
C1 C 0.6992(2) -0.0022(2) 0.4398(2) 0.0266(4) Uani 1 1 d . . . . .
H1 H 0.6612 -0.0720 0.4254 0.032 Uiso 1 1 calc R . . . .
C2 C 0.8234(2) 0.0285(2) 0.37059(18) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.8830(2) -0.0428(2) 0.2842(2) 0.0286(4) Uani 1 1 d . . . . .
H3 H 0.8414 -0.1105 0.2699 0.034 Uiso 1 1 calc R . . . .
C4 C 1.0031(3) -0.0126(2) 0.2207(2) 0.0319(5) Uani 1 1 d . . . . .
H4 H 1.0425 -0.0593 0.1629 0.038 Uiso 1 1 calc R . . . .
C5 C 1.0658(2) 0.0885(2) 0.2431(2) 0.0308(5) Uani 1 1 d . . . . .
H5 H 1.1479 0.1075 0.2004 0.037 Uiso 1 1 calc R . . . .
C6 C 1.0084(2) 0.1609(2) 0.32735(19) 0.0260(4) Uani 1 1 d . . . . .
H6 H 1.0512 0.2281 0.3410 0.031 Uiso 1 1 calc R . . . .
C7 C 0.8852(2) 0.1321(2) 0.39194(18) 0.0212(4) Uani 1 1 d . . . . .
C8 C 0.8155(2) 0.2035(2) 0.47971(18) 0.0219(4) Uani 1 1 d . . . . .
C9 C 0.8368(2) 0.3100(2) 0.52590(19) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.9091 0.3584 0.5033 0.028 Uiso 1 1 calc R . . . .
C10 C 0.7298(2) 0.3315(2) 0.61267(18) 0.0218(4) Uani 1 1 d . . . . .
C11 C 0.6429(2) 0.2391(2) 0.61804(18) 0.0222(4) Uani 1 1 d . . . . .
C12 C 0.5103(2) 0.2289(2) 0.67997(19) 0.0254(4) Uani 1 1 d . . . . .
C13 C 0.7030(2) 0.4328(2) 0.69085(18) 0.0227(4) Uani 1 1 d . . . . .
H13 H 0.6784 0.3822 0.7693 0.027 Uiso 1 1 calc R . . . .
C14 C 0.8465(2) 0.4721(2) 0.70373(19) 0.0242(4) Uani 1 1 d . . . . .
C15 C 1.0651(3) 0.4222(3) 0.8235(2) 0.0395(6) Uani 1 1 d . . . . .
H15A H 1.0459 0.5224 0.8229 0.047 Uiso 1 1 calc R . . . .
H15B H 1.1339 0.4025 0.7614 0.047 Uiso 1 1 calc R . . . .
C16 C 1.1328(4) 0.3257(3) 0.9400(3) 0.0560(8) Uani 1 1 d . . . . .
H16A H 1.1537 0.2268 0.9389 0.084 Uiso 1 1 calc GR . . . .
H16B H 1.0628 0.3447 1.0006 0.084 Uiso 1 1 calc GR . . . .
H16C H 1.2256 0.3432 0.9558 0.084 Uiso 1 1 calc GR . . . .
C17 C 0.5689(2) 0.5705(2) 0.6430(2) 0.0274(4) Uani 1 1 d . . . . .
H17A H 0.6013 0.6348 0.5767 0.033 Uiso 1 1 calc R . . . .
H17B H 0.4868 0.5445 0.6149 0.033 Uiso 1 1 calc R . . . .
C18 C 0.5119(2) 0.6482(2) 0.73698(19) 0.0258(4) Uani 1 1 d . . . . .
C19 C 0.4070(3) 0.6057(3) 0.8161(2) 0.0353(5) Uani 1 1 d . . . . .
H19 H 0.3733 0.5295 0.8103 0.042 Uiso 1 1 calc R . . . .
C20 C 0.3519(3) 0.6747(3) 0.9032(2) 0.0373(5) Uani 1 1 d . . . . .
H20 H 0.2819 0.6454 0.9554 0.045 Uiso 1 1 calc R . . . .
C21 C 0.4027(3) 0.7876(2) 0.9112(2) 0.0309(5) Uani 1 1 d . . . . .
C22 C 0.5078(3) 0.8313(2) 0.8351(2) 0.0314(5) Uani 1 1 d . . . . .
H22 H 0.5422 0.9068 0.8419 0.038 Uiso 1 1 calc R . . . .
C23 C 0.5614(2) 0.7612(2) 0.7483(2) 0.0298(5) Uani 1 1 d . . . . .
H23 H 0.6320 0.7906 0.6967 0.036 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
Br1 C21 1.896(2) . ?
O1 C14 1.207(3) . ?
O2 C14 1.329(3) . ?
O2 C15 1.457(3) . ?
N1 N2 1.371(2) . ?
N1 C1 1.298(3) . ?
N2 C8 1.381(2) . ?
N2 C11 1.377(2) . ?
N3 C12 1.145(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.439(3) . ?
C2 C3 1.401(3) . ?
C2 C7 1.412(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.374(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.399(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.400(3) . ?
C7 C8 1.437(3) . ?
C8 C9 1.392(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.404(3) . ?
C10 C11 1.388(3) . ?
C10 C13 1.512(3) . ?
C11 C12 1.414(3) . ?
C13 H13 0.9800 . ?
C13 C14 1.516(3) . ?
C13 C17 1.545(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.486(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.511(3) . ?
C18 C19 1.393(3) . ?
C18 C23 1.387(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(3) . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(3) . ?
C23 H23 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
C14 O2 C15 115.77(17) . . ?
C1 N1 N2 114.19(16) . . ?
N1 N2 C8 127.83(16) . . ?
N1 N2 C11 122.68(16) . . ?
C11 N2 C8 109.48(16) . . ?
N1 C1 H1 117.1 . . ?
N1 C1 C2 125.71(18) . . ?
C2 C1 H1 117.1 . . ?
C3 C2 C1 121.24(19) . . ?
C3 C2 C7 120.31(19) . . ?
C7 C2 C1 118.45(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.3 . . ?
C5 C6 C7 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C2 C7 C8 117.07(17) . . ?
C6 C7 C2 119.24(18) . . ?
C6 C7 C8 123.68(18) . . ?
N2 C8 C7 116.72(17) . . ?
N2 C8 C9 107.21(17) . . ?
C9 C8 C7 136.07(18) . . ?
C8 C9 H9 126.0 . . ?
C8 C9 C10 107.97(17) . . ?
C10 C9 H9 126.0 . . ?
C9 C10 C13 130.31(17) . . ?
C11 C10 C9 107.53(17) . . ?
C11 C10 C13 122.17(18) . . ?
N2 C11 C10 107.80(17) . . ?
N2 C11 C12 121.20(17) . . ?
C10 C11 C12 130.57(19) . . ?
N3 C12 C11 177.9(2) . . ?
C10 C13 H13 108.2 . . ?
C10 C13 C14 109.98(16) . . ?
C10 C13 C17 111.87(17) . . ?
C14 C13 H13 108.2 . . ?
C14 C13 C17 110.39(16) . . ?
C17 C13 H13 108.2 . . ?
O1 C14 O2 124.19(19) . . ?
O1 C14 C13 124.0(2) . . ?
O2 C14 C13 111.85(17) . . ?
O2 C15 H15A 110.2 . . ?
O2 C15 H15B 110.2 . . ?
O2 C15 C16 107.5(2) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.3 . . ?
C13 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C13 111.51(18) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C19 C18 C17 119.82(19) . . ?
C23 C18 C17 122.07(19) . . ?
C23 C18 C19 118.1(2) . . ?
C18 C19 H19 119.3 . . ?
C20 C19 C18 121.4(2) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 118.9(2) . . ?
C21 C20 H20 120.5 . . ?
C20 C21 Br1 119.51(18) . . ?
C20 C21 C22 121.1(2) . . ?
C22 C21 Br1 119.32(17) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.1(2) . . ?
C23 C22 H22 120.5 . . ?
C18 C23 H23 119.3 . . ?
C22 C23 C18 121.3(2) . . ?
C22 C23 H23 119.3 . . ?

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 C21 C22 C23 -177.50(17) . . . . ?
N1 N2 C8 C7 0.2(3) . . . . ?
N1 N2 C8 C9 -179.72(18) . . . . ?
N1 N2 C11 C10 179.38(17) . . . . ?
N1 N2 C11 C12 -7.4(3) . . . . ?
N1 C1 C2 C3 -179.2(2) . . . . ?
N1 C1 C2 C7 1.1(3) . . . . ?
N2 N1 C1 C2 0.4(3) . . . . ?
N2 C8 C9 C10 0.5(2) . . . . ?
C1 N1 N2 C8 -1.1(3) . . . . ?
C1 N1 N2 C11 179.52(19) . . . . ?
C1 C2 C3 C4 -179.1(2) . . . . ?
C1 C2 C7 C6 178.55(19) . . . . ?
C1 C2 C7 C8 -1.9(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C7 C8 N2 1.3(3) . . . . ?
C2 C7 C8 C9 -178.8(2) . . . . ?
C3 C2 C7 C6 -1.2(3) . . . . ?
C3 C2 C7 C8 178.38(18) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C2 0.8(3) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C6 C7 C8 N2 -179.18(18) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
C8 N2 C11 C10 -0.1(2) . . . . ?
C8 N2 C11 C12 173.10(19) . . . . ?
C8 C9 C10 C11 -0.6(2) . . . . ?
C8 C9 C10 C13 179.5(2) . . . . ?
C9 C10 C11 N2 0.4(2) . . . . ?
C9 C10 C11 C12 -171.9(2) . . . . ?
C9 C10 C13 C14 -23.5(3) . . . . ?
C9 C10 C13 C17 99.6(2) . . . . ?
C10 C13 C14 O1 80.3(2) . . . . ?
C10 C13 C14 O2 -99.4(2) . . . . ?
C10 C13 C17 C18 162.58(17) . . . . ?
C11 N2 C8 C7 179.68(17) . . . . ?
C11 N2 C8 C9 -0.3(2) . . . . ?
C11 C10 C13 C14 156.63(19) . . . . ?
C11 C10 C13 C17 -80.3(2) . . . . ?
C13 C10 C11 N2 -179.65(17) . . . . ?
C13 C10 C11 C12 8.0(3) . . . . ?
C13 C17 C18 C19 -84.4(2) . . . . ?
C13 C17 C18 C23 95.1(2) . . . . ?
C14 O2 C15 C16 180.0(2) . . . . ?
C14 C13 C17 C18 -74.6(2) . . . . ?
C15 O2 C14 O1 -1.2(3) . . . . ?
C15 O2 C14 C13 178.52(18) . . . . ?
C17 C13 C14 O1 -43.6(3) . . . . ?
C17 C13 C14 O2 136.70(18) . . . . ?
C17 C18 C19 C20 -179.8(2) . . . . ?
C17 C18 C23 C22 180.0(2) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C18 C23 C22 -0.5(3) . . . . ?
C19 C20 C21 Br1 177.64(19) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
C23 C18 C19 C20 0.7(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_sa3602
_database_code_depnum_ccdc_archive 'CCDC 1465124'
_audit_update_record             
;
2016-03-12 deposited with the CCDC.
2016-08-11 downloaded from the CCDC.
;
_audit_creation_date             2014-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H19 Br N4 O2'
_chemical_formula_sum            'C24 H19 Br N4 O2'
_chemical_formula_weight         475.34
_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'
Br Br -0.2901 2.4595 '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                   8.775(2)
_cell_length_b                   16.891(3)
_cell_length_c                   14.538(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.444(3)
_cell_angle_gamma                90
_cell_volume                     2150.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5740
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4822
_cell_measurement_theta_min      2.4116
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.940
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.159
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15229
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         2.412
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             5080
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0134
_diffrn_orient_matrix_UB_12      0.0051
_diffrn_orient_matrix_UB_13      -0.1133
_diffrn_orient_matrix_UB_21      -0.0479
_diffrn_orient_matrix_UB_22      -0.0346
_diffrn_orient_matrix_UB_23      0.0041
_diffrn_orient_matrix_UB_31      -0.0401
_diffrn_orient_matrix_UB_32      0.0560
_diffrn_orient_matrix_UB_33      0.0031
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4187
_reflns_number_total             4899
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2013)'
_computing_structure_solution    
;
'SHELXS (Sheldrick, 2013)'

;
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     366
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     306
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0380P)²+1.1091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1130
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C17A-C16 = C21A-C16 = C18A-C17A = C19A-C18A = C20A-C19A = C21A-C20A
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
O2 \\sim O2A \\sim C13A \\sim C14A \\sim C14 \\sim C13: within 1.7A with sigma
of 0.02 and sigma for terminal atoms of 0.04
Br1 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim Br1A \\sim C20A
\\sim C19A \\sim C18A \\sim C17A \\sim C21A: within 1.7A with sigma of 0.02 and
sigma for terminal atoms of 0.04
Uanis(Br1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O2) \\sim Ueq, Uanis(O2A) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C13A)
\\sim Ueq, Uanis(C14A) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(Br1) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19)
\\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(Br1A) \\sim Ueq,
Uanis(C20A) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C18A) \\sim Ueq,
Uanis(C17A) \\sim Ueq, Uanis(C21A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O2A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=Sof(H14D)=Sof(H14E)=
 Sof(H14F)=1-FVAR(1)
 Sof(O2)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=
 FVAR(1)
 Sof(Br1A)=Sof(C20A)=Sof(H20A)=Sof(C19A)=Sof(C18A)=Sof(H18A)=1-FVAR(2)
 Sof(Br1)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(C20)=Sof(H20)=FVAR(2)
 Sof(C17A)=Sof(H17A)=Sof(C21A)=Sof(H21A)=1-FVAR(3)
 Sof(C17)=Sof(H17)=Sof(C21)=Sof(H21)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C17(H17), C18(H18), C20(H20),
 C21(H21), C20A(H20A), C18A(H18A), C17A(H17A), C21A(H21A)
5.d X=CH2 refined with riding coordinates:
 C22(H22A,H22B)
5.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C14A(H14D,H14E,H14F)
;
_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
Br1 Br 0.5206(6) 0.65434(11) 1.01452(13) 0.0561(6) Uani 0.604(16) 1 d . U P A 1
O1 O 0.5260(2) 0.36975(10) 0.49296(11) 0.0385(4) Uani 1 1 d . . . . .
O2 O 0.4222(10) 0.2688(7) 0.5618(7) 0.0316(14) Uani 0.648(17) 1 d . U P B 1
N1 N 0.2357(2) 0.31562(10) 0.71362(12) 0.0262(4) Uani 1 1 d . . . . .
N2 N 0.1717(2) 0.27765(11) 0.78796(12) 0.0321(4) Uani 1 1 d . . . . .
N3 N 0.0777(3) 0.47861(16) 0.81482(18) 0.0602(7) Uani 1 1 d . . . . .
N4 N -0.1060(3) 0.34706(16) 0.58621(19) 0.0552(6) Uani 1 1 d . . . . .
C1 C 0.4194(2) 0.39149(12) 0.63981(13) 0.0236(4) Uani 1 1 d . . . . .
C2 C 0.2586(2) 0.42501(12) 0.61813(14) 0.0252(4) Uani 1 1 d . . . . .
C3 C 0.1474(2) 0.38344(13) 0.68013(15) 0.0290(5) Uani 1 1 d . . . . .
C4 C 0.3950(2) 0.34267(12) 0.72765(14) 0.0237(4) Uani 1 1 d . . . . .
H4 H 0.3995 0.3796 0.7798 0.028 Uiso 1 1 calc R . . . .
C5 C 0.4931(3) 0.27287(13) 0.75516(14) 0.0274(4) Uani 1 1 d . . . . .
C6 C 0.6440(3) 0.26224(15) 0.73474(16) 0.0366(5) Uani 1 1 d . . . . .
H6 H 0.6899 0.2977 0.6961 0.044 Uiso 1 1 calc R . . . .
C7 C 0.7264(3) 0.19881(17) 0.77191(18) 0.0469(7) Uani 1 1 d . . . . .
H7 H 0.8275 0.1918 0.7577 0.056 Uiso 1 1 calc R . . . .
C8 C 0.6601(4) 0.14594(16) 0.82986(19) 0.0502(7) Uani 1 1 d . . . . .
H8 H 0.7167 0.1038 0.8549 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5100(4) 0.15565(14) 0.85062(17) 0.0437(6) Uani 1 1 d . . . . .
H9 H 0.4656 0.1200 0.8897 0.052 Uiso 1 1 calc R . . . .
C10 C 0.4243(3) 0.21882(13) 0.81323(14) 0.0303(5) Uani 1 1 d . . . . .
C11 C 0.2653(3) 0.23139(13) 0.83343(15) 0.0333(5) Uani 1 1 d . . . . .
H11 H 0.2287 0.2039 0.8829 0.040 Uiso 1 1 calc R . . . .
C12 C 0.4583(2) 0.34250(12) 0.55511(14) 0.0265(4) Uani 1 1 d . . . . .
C13 C 0.4699(10) 0.2156(4) 0.4889(5) 0.0388(15) Uani 0.648(17) 1 d . U P B 1
H13A H 0.5794 0.2190 0.4838 0.047 Uiso 0.648(17) 1 calc R . P B 1
H13B H 0.4196 0.2302 0.4301 0.047 Uiso 0.648(17) 1 calc R . P B 1
C14 C 0.4261(13) 0.1336(4) 0.5143(6) 0.071(2) Uani 0.648(17) 1 d . U P B 1
H14A H 0.4664 0.1220 0.5757 0.106 Uiso 0.648(17) 1 calc GR . P B 1
H14B H 0.4668 0.0967 0.4720 0.106 Uiso 0.648(17) 1 calc GR . P B 1
H14C H 0.3168 0.1292 0.5116 0.106 Uiso 0.648(17) 1 calc GR . P B 1
C15 C 0.5420(3) 0.45765(13) 0.65326(15) 0.0290(5) Uani 1 1 d . . . . .
H15A H 0.6420 0.4337 0.6499 0.035 Uiso 1 1 calc R . . . .
H15B H 0.5285 0.4946 0.6024 0.035 Uiso 1 1 calc R . . . .
C16 C 0.5400(3) 0.50354(13) 0.74194(15) 0.0298(5) Uani 1 1 d D . . . .
C17 C 0.6348(17) 0.4903(9) 0.8218(11) 0.034(2) Uani 0.57(5) 1 d . U P A 1
H17 H 0.7052 0.4491 0.8216 0.041 Uiso 0.57(5) 1 calc R . P A 1
C18 C 0.6284(11) 0.5358(7) 0.9008(6) 0.0402(19) Uani 0.604(16) 1 d . U P A 1
H18 H 0.6973 0.5271 0.9509 0.048 Uiso 0.604(16) 1 calc R . P A 1
C19 C 0.5207(11) 0.5930(7) 0.9045(8) 0.0338(17) Uani 0.604(16) 1 d . U P A 1
C20 C 0.4208(12) 0.6103(7) 0.8341(7) 0.0309(16) Uani 0.604(16) 1 d . U P A 1
H20 H 0.3449 0.6484 0.8377 0.037 Uiso 0.604(16) 1 calc R . P A 1
C21 C 0.441(2) 0.5659(12) 0.7548(14) 0.034(3) Uani 0.57(5) 1 d . U P A 1
H21 H 0.3790 0.5801 0.7032 0.041 Uiso 0.57(5) 1 calc R . P A 1
C22 C 0.2175(3) 0.47984(14) 0.55703(15) 0.0319(5) Uani 1 1 d . . . . .
H22A H 0.2901 0.5027 0.5212 0.038 Uiso 1 1 calc R . . . .
H22B H 0.1160 0.4957 0.5497 0.038 Uiso 1 1 calc R . . . .
C23 C 0.1061(3) 0.43790(15) 0.75605(17) 0.0389(6) Uani 1 1 d . . . . .
C24 C 0.0046(3) 0.35982(15) 0.62830(18) 0.0374(5) Uani 1 1 d . . . . .
O2A O 0.3792(18) 0.2703(14) 0.5518(14) 0.033(3) Uani 0.352(17) 1 d . U P B 2
C13A C 0.4075(19) 0.2143(9) 0.4777(9) 0.041(3) Uani 0.352(17) 1 d . U P B 2
H13C H 0.4534 0.2416 0.4276 0.049 Uiso 0.352(17) 1 calc R . P B 2
H13D H 0.3120 0.1910 0.4540 0.049 Uiso 0.352(17) 1 calc R . P B 2
C14A C 0.511(3) 0.1516(10) 0.5150(9) 0.078(5) Uani 0.352(17) 1 d . U P B 2
H14D H 0.4690 0.1277 0.5676 0.118 Uiso 0.352(17) 1 calc GR . P B 2
H14E H 0.6090 0.1744 0.5331 0.118 Uiso 0.352(17) 1 calc GR . P B 2
H14F H 0.5240 0.1121 0.4686 0.118 Uiso 0.352(17) 1 calc GR . P B 2
Br1A Br 0.5792(15) 0.6431(5) 1.0125(2) 0.0795(16) Uani 0.396(16) 1 d . U P A 2
C20A C 0.4546(18) 0.5992(11) 0.8353(13) 0.040(3) Uani 0.396(16) 1 d D U P A 2
H20A H 0.3895 0.6411 0.8464 0.048 Uiso 0.396(16) 1 calc R . P A 2
C19A C 0.5671(15) 0.5838(10) 0.9039(11) 0.030(3) Uani 0.396(16) 1 d D U P A 2
C18A C 0.6739(15) 0.5257(9) 0.8875(10) 0.035(2) Uani 0.396(16) 1 d D U P A 2
H18A H 0.7521 0.5138 0.9314 0.042 Uiso 0.396(16) 1 calc R . P A 2
C17A C 0.6610(19) 0.4857(11) 0.8041(11) 0.035(3) Uani 0.43(5) 1 d D U P A 2
H17A H 0.7325 0.4476 0.7901 0.042 Uiso 0.43(5) 1 calc R . P A 2
C21A C 0.427(3) 0.5600(16) 0.7517(16) 0.033(3) Uani 0.43(5) 1 d D U P A 2
H21A H 0.3452 0.5699 0.7093 0.039 Uiso 0.43(5) 1 calc R . P A 2


_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 C19 1.906(12) . ?
O1 C12 1.202(3) . ?
O2 C12 1.290(12) . ?
O2 C13 1.470(13) . ?
N1 N2 1.403(2) . ?
N1 C3 1.451(3) . ?
N1 C4 1.473(3) . ?
N2 C11 1.287(3) . ?
N3 C23 1.136(3) . ?
N4 C24 1.136(3) . ?
C1 C2 1.535(3) . ?
C1 C4 1.546(3) . ?
C1 C12 1.539(3) . ?
C1 C15 1.556(3) . ?
C2 C3 1.537(3) . ?
C2 C22 1.318(3) . ?
C3 C23 1.498(3) . ?
C3 C24 1.478(3) . ?
C4 C5 1.500(3) . ?
C5 C6 1.386(3) . ?
C5 C10 1.404(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.380(4) . ?
C8 C9 1.379(4) . ?
C9 C10 1.396(3) . ?
C10 C11 1.459(3) . ?
C12 O2A 1.40(2) . ?
C13 C14 1.490(10) . ?
C15 C16 1.505(3) . ?
C16 C17 1.405(9) . ?
C16 C21 1.385(10) . ?
C16 C17A 1.386(9) . ?
C16 C21A 1.391(10) . ?
C17 C18 1.39(2) . ?
C18 C19 1.356(10) . ?
C19 C20 1.339(10) . ?
C20 C21 1.396(13) . ?
O2A C13A 1.47(2) . ?
C13A C14A 1.48(2) . ?
Br1A C19A 1.867(16) . ?
C20A C19A 1.386(9) . ?
C20A C21A 1.392(10) . ?
C19A C18A 1.387(9) . ?
C18A C17A 1.387(10) . ?

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
C12 O2 C13 117.0(8) . . ?
N2 N1 C3 112.91(16) . . ?
N2 N1 C4 117.11(17) . . ?
C3 N1 C4 106.54(16) . . ?
C11 N2 N1 113.62(18) . . ?
C2 C1 C4 101.27(15) . . ?
C2 C1 C12 106.23(16) . . ?
C2 C1 C15 112.40(17) . . ?
C4 C1 C15 114.10(17) . . ?
C12 C1 C4 115.00(16) . . ?
C12 C1 C15 107.56(16) . . ?
C1 C2 C3 108.59(17) . . ?
C22 C2 C1 127.43(19) . . ?
C22 C2 C3 124.0(2) . . ?
N1 C3 C2 102.29(16) . . ?
N1 C3 C23 112.68(19) . . ?
N1 C3 C24 112.17(19) . . ?
C23 C3 C2 109.99(18) . . ?
C24 C3 C2 111.90(18) . . ?
C24 C3 C23 107.81(19) . . ?
N1 C4 C1 103.19(16) . . ?
N1 C4 C5 108.53(17) . . ?
C5 C4 C1 122.28(17) . . ?
C6 C5 C4 125.8(2) . . ?
C6 C5 C10 119.7(2) . . ?
C10 C5 C4 114.25(19) . . ?
C7 C6 C5 120.0(2) . . ?
C8 C7 C6 120.6(3) . . ?
C9 C8 C7 120.0(2) . . ?
C8 C9 C10 120.3(2) . . ?
C5 C10 C11 118.5(2) . . ?
C9 C10 C5 119.3(2) . . ?
C9 C10 C11 122.1(2) . . ?
N2 C11 C10 124.99(19) . . ?
O1 C12 O2 124.1(5) . . ?
O1 C12 C1 122.62(19) . . ?
O1 C12 O2A 125.0(9) . . ?
O2 C12 C1 113.0(5) . . ?
O2A C12 C1 111.2(9) . . ?
O2 C13 C14 107.5(7) . . ?
C16 C15 C1 115.71(17) . . ?
C17 C16 C15 126.0(8) . . ?
C21 C16 C15 123.1(8) . . ?
C21 C16 C17 110.8(13) . . ?
C17A C16 C15 113.5(8) . . ?
C17A C16 C21A 127.3(11) . . ?
C21A C16 C15 119.1(8) . . ?
C18 C17 C16 123.0(12) . . ?
C19 C18 C17 119.4(9) . . ?
C18 C19 Br1 117.1(8) . . ?
C20 C19 Br1 119.3(7) . . ?
C20 C19 C18 123.5(10) . . ?
C19 C20 C21 113.9(10) . . ?
C16 C21 C20 129.2(13) . . ?
N3 C23 C3 178.4(3) . . ?
N4 C24 C3 175.1(3) . . ?
C12 O2A C13A 118.7(14) . . ?
O2A C13A C14A 108.7(12) . . ?
C19A C20A C21A 128.3(15) . . ?
C20A C19A Br1A 120.6(11) . . ?
C20A C19A C18A 117.9(13) . . ?
C18A C19A Br1A 121.4(10) . . ?
C17A C18A C19A 118.3(14) . . ?
C16 C17A C18A 118.9(13) . . ?
C16 C21A C20A 109.0(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
Br1 C19 C20 C21 174.7(14) . . . . ?
O1 C12 O2A C13A 15.2(16) . . . . ?
O2 C12 O2A C13A -78(4) . . . . ?
N1 N2 C11 C10 1.0(3) . . . . ?
N1 C4 C5 C6 148.4(2) . . . . ?
N1 C4 C5 C10 -37.3(2) . . . . ?
N2 N1 C3 C2 166.57(16) . . . . ?
N2 N1 C3 C23 48.5(2) . . . . ?
N2 N1 C3 C24 -73.4(2) . . . . ?
N2 N1 C4 C1 -171.92(16) . . . . ?
N2 N1 C4 C5 57.0(2) . . . . ?
C1 C2 C3 N1 -15.2(2) . . . . ?
C1 C2 C3 C23 104.7(2) . . . . ?
C1 C2 C3 C24 -135.48(19) . . . . ?
C1 C4 C5 C6 28.7(3) . . . . ?
C1 C4 C5 C10 -157.07(19) . . . . ?
C1 C12 O2A C13A -177.3(10) . . . . ?
C1 C15 C16 C17 98.3(9) . . . . ?
C1 C15 C16 C21 -81.7(14) . . . . ?
C1 C15 C16 C17A 107.7(10) . . . . ?
C1 C15 C16 C21A -75.4(18) . . . . ?
C2 C1 C4 N1 31.82(19) . . . . ?
C2 C1 C4 C5 154.11(19) . . . . ?
C2 C1 C12 O1 93.1(2) . . . . ?
C2 C1 C12 O2 -92.3(5) . . . . ?
C2 C1 C12 O2A -74.8(8) . . . . ?
C2 C1 C15 C16 73.4(2) . . . . ?
C3 N1 N2 C11 -163.04(19) . . . . ?
C3 N1 C4 C1 -44.47(19) . . . . ?
C3 N1 C4 C5 -175.54(16) . . . . ?
C4 N1 N2 C11 -38.7(3) . . . . ?
C4 N1 C3 C2 36.7(2) . . . . ?
C4 N1 C3 C23 -81.4(2) . . . . ?
C4 N1 C3 C24 156.73(18) . . . . ?
C4 C1 C2 C3 -10.3(2) . . . . ?
C4 C1 C2 C22 170.0(2) . . . . ?
C4 C1 C12 O1 -155.8(2) . . . . ?
C4 C1 C12 O2 18.8(5) . . . . ?
C4 C1 C12 O2A 36.3(8) . . . . ?
C4 C1 C15 C16 -41.1(2) . . . . ?
C4 C5 C6 C7 173.6(2) . . . . ?
C4 C5 C10 C9 -173.8(2) . . . . ?
C4 C5 C10 C11 5.4(3) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C5 C10 C11 N2 15.6(3) . . . . ?
C6 C5 C10 C9 0.9(3) . . . . ?
C6 C5 C10 C11 -179.9(2) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C5 -0.8(4) . . . . ?
C8 C9 C10 C11 -179.9(2) . . . . ?
C9 C10 C11 N2 -165.2(2) . . . . ?
C10 C5 C6 C7 -0.3(4) . . . . ?
C12 O2 C13 C14 176.1(10) . . . . ?
C12 C1 C2 C3 110.16(18) . . . . ?
C12 C1 C2 C22 -69.5(3) . . . . ?
C12 C1 C4 N1 -82.2(2) . . . . ?
C12 C1 C4 C5 40.1(3) . . . . ?
C12 C1 C15 C16 -169.99(18) . . . . ?
C12 O2A C13A C14A 101(2) . . . . ?
C13 O2 C12 O1 0.9(8) . . . . ?
C13 O2 C12 C1 -173.6(4) . . . . ?
C13 O2 C12 O2A 100(5) . . . . ?
C15 C1 C2 C3 -132.46(18) . . . . ?
C15 C1 C2 C22 47.8(3) . . . . ?
C15 C1 C4 N1 152.81(17) . . . . ?
C15 C1 C4 C5 -84.9(2) . . . . ?
C15 C1 C12 O1 -27.5(3) . . . . ?
C15 C1 C12 O2 147.1(5) . . . . ?
C15 C1 C12 O2A 164.6(8) . . . . ?
C15 C16 C17 C18 179.0(8) . . . . ?
C15 C16 C21 C20 176.0(18) . . . . ?
C15 C16 C17A C18A 178.4(13) . . . . ?
C15 C16 C21A C20A -175.1(16) . . . . ?
C16 C17 C18 C19 3.9(18) . . . . ?
C17 C16 C21 C20 -4(3) . . . . ?
C17 C16 C17A C18A -32(4) . . . . ?
C17 C16 C21A C20A 11(3) . . . . ?
C17 C18 C19 Br1 -179.0(9) . . . . ?
C17 C18 C19 C20 -2.0(16) . . . . ?
C18 C19 C20 C21 -2(2) . . . . ?
C19 C20 C21 C16 6(3) . . . . ?
C21 C16 C17 C18 -1.1(18) . . . . ?
C21 C16 C17A C18A 8(2) . . . . ?
C21 C16 C21A C20A -47(16) . . . . ?
C22 C2 C3 N1 164.5(2) . . . . ?
C22 C2 C3 C23 -75.6(3) . . . . ?
C22 C2 C3 C24 44.2(3) . . . . ?
Br1A C19A C18A C17A -177.8(13) . . . . ?
C20A C19A C18A C17A -1(2) . . . . ?
C19A C20A C21A C16 -5(4) . . . . ?
C19A C18A C17A C16 -2(2) . . . . ?
C17A C16 C17 C18 144(6) . . . . ?
C17A C16 C21 C20 -14(3) . . . . ?
C17A C16 C21A C20A 1(4) . . . . ?
C21A C16 C17 C18 -7(2) . . . . ?
C21A C16 C21 C20 121(20) . . . . ?
C21A C16 C17A C18A 2(3) . . . . ?
C21A C20A C19A Br1A -178(2) . . . . ?
C21A C20A C19A C18A 5(3) . . . . ?

