# Electronic Supplementary Material (ESI) for Nanoscale.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ic19064
_database_code_depnum_ccdc_archive 'CCDC 1894255'
loop_
_audit_author_name
_audit_author_address
'Sin-Yu Chen'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-01-29 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H24 N2 O2'
_chemical_formula_weight         432.50

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.8798(4)
_cell_length_b                   11.8215(4)
_cell_length_c                   35.5224(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.737(4)
_cell_angle_gamma                90.00
_cell_volume                     4568.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4403
_cell_measurement_theta_min      3.9300
_cell_measurement_theta_max      76.6790

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1824
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94975
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20248
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0483
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.94
_diffrn_reflns_theta_max         67.98
_reflns_number_total             8316
_reflns_number_gt                5407
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0707P)²+0.0738P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8316
_refine_ls_number_parameters     595
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1542
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6008(2) 0.65496(16) 0.47973(6) 0.0768(6) Uani 1 1 d . . .
O2 O 0.39115(18) -0.09673(15) 0.42927(5) 0.0635(5) Uani 1 1 d . . .
N1 N 1.0974(2) 0.56139(17) 0.28438(6) 0.0592(6) Uani 1 1 d . . .
N2 N 0.69020(19) 0.27015(16) 0.39331(6) 0.0498(5) Uani 1 1 d . . .
C1 C 1.3585(2) 0.3022(2) 0.17047(8) 0.0601(7) Uani 1 1 d . . .
H1A H 1.4172 0.2899 0.1513 0.072 Uiso 1 1 calc R . .
C2 C 1.3607(2) 0.4002(2) 0.19139(7) 0.0576(6) Uani 1 1 d . . .
H2A H 1.4214 0.4560 0.1867 0.069 Uiso 1 1 calc R . .
C3 C 1.2750(2) 0.4182(2) 0.21925(7) 0.0516(6) Uani 1 1 d . . .
H3A H 1.2780 0.4862 0.2335 0.062 Uiso 1 1 calc R . .
C4 C 1.1844(2) 0.33839(19) 0.22674(6) 0.0444(5) Uani 1 1 d . . .
C5 C 1.1824(3) 0.2391(2) 0.20538(8) 0.0588(7) Uani 1 1 d . . .
H5A H 1.1214 0.1833 0.2097 0.071 Uiso 1 1 calc R . .
C6 C 1.2696(3) 0.2223(2) 0.17779(8) 0.0638(7) Uani 1 1 d . . .
H6A H 1.2681 0.1542 0.1636 0.077 Uiso 1 1 calc R . .
C7 C 1.0944(2) 0.35874(18) 0.25699(6) 0.0446(5) Uani 1 1 d . . .
C8 C 1.0166(2) 0.28006(19) 0.27048(6) 0.0472(5) Uani 1 1 d . . .
H8A H 1.0222 0.2086 0.2584 0.057 Uiso 1 1 calc R . .
C9 C 0.9258(2) 0.28466(19) 0.30014(6) 0.0451(5) Uani 1 1 d . . .
C10 C 0.8784(2) 0.38299(19) 0.31637(7) 0.0472(5) Uani 1 1 d . . .
H10A H 0.9019 0.4546 0.3067 0.057 Uiso 1 1 calc R . .
C11 C 0.7987(2) 0.37808(19) 0.34605(7) 0.0477(5) Uani 1 1 d . . .
H11A H 0.7673 0.4463 0.3563 0.057 Uiso 1 1 calc R . .
C12 C 0.7628(2) 0.27441(19) 0.36150(6) 0.0448(5) Uani 1 1 d . . .
C13 C 0.8041(2) 0.17536(19) 0.34419(6) 0.0460(5) Uani 1 1 d . . .
H13A H 0.7775 0.1037 0.3531 0.055 Uiso 1 1 calc R . .
C14 C 0.8833(2) 0.18155(19) 0.31425(7) 0.0475(5) Uani 1 1 d . . .
H14A H 0.9099 0.1134 0.3028 0.057 Uiso 1 1 calc R . .
C15 C 0.6665(2) 0.36944(19) 0.41511(6) 0.0471(5) Uani 1 1 d . . .
C16 C 0.7605(2) 0.4246(2) 0.43433(7) 0.0571(6) Uani 1 1 d . . .
H16A H 0.8422 0.3967 0.4332 0.069 Uiso 1 1 calc R . .
C17 C 0.7350(3) 0.5206(2) 0.45526(7) 0.0613(7) Uani 1 1 d . . .
H17A H 0.7999 0.5591 0.4680 0.074 Uiso 1 1 calc R . .
C18 C 0.6161(3) 0.5608(2) 0.45782(7) 0.0554(6) Uani 1 1 d . . .
C19 C 0.5219(2) 0.5061(2) 0.43869(7) 0.0548(6) Uani 1 1 d . . .
H19A H 0.4399 0.5331 0.4402 0.066 Uiso 1 1 calc R . .
C20 C 0.5488(2) 0.4110(2) 0.41716(7) 0.0511(6) Uani 1 1 d . . .
H20A H 0.4845 0.3740 0.4036 0.061 Uiso 1 1 calc R . .
C21 C 0.6155(2) 0.17297(19) 0.40097(6) 0.0455(5) Uani 1 1 d . . .
C22 C 0.6225(2) 0.1219(2) 0.43605(7) 0.0497(6) Uani 1 1 d . . .
H22A H 0.6795 0.1489 0.4544 0.060 Uiso 1 1 calc R . .
C23 C 0.5465(2) 0.0315(2) 0.44438(7) 0.0525(6) Uani 1 1 d . . .
H23A H 0.5522 -0.0037 0.4684 0.063 Uiso 1 1 calc R . .
C24 C 0.4624(2) -0.00794(19) 0.41803(7) 0.0484(5) Uani 1 1 d . . .
C25 C 0.4563(2) 0.0413(2) 0.38271(7) 0.0510(6) Uani 1 1 d . . .
H25A H 0.4004 0.0134 0.3642 0.061 Uiso 1 1 calc R . .
C26 C 0.5329(2) 0.1318(2) 0.37468(7) 0.0506(6) Uani 1 1 d . . .
H26A H 0.5281 0.1661 0.3505 0.061 Uiso 1 1 calc R . .
C27 C 1.0953(2) 0.4714(2) 0.27260(7) 0.0472(5) Uani 1 1 d . . .
C28 C 0.4800(4) 0.6970(2) 0.48398(9) 0.0856(10) Uani 1 1 d . . .
H28A H 0.4821 0.7644 0.5000 0.128 Uiso 1 1 calc R . .
H28B H 0.4288 0.6388 0.4956 0.128 Uiso 1 1 calc R . .
H28C H 0.4455 0.7168 0.4592 0.128 Uiso 1 1 calc R . .
C29 C 0.2992(3) -0.1361(2) 0.40370(9) 0.0736(8) Uani 1 1 d . . .
H29A H 0.2548 -0.1994 0.4151 0.110 Uiso 1 1 calc R . .
H29B H 0.3379 -0.1615 0.3804 0.110 Uiso 1 1 calc R . .
H29C H 0.2415 -0.0746 0.3980 0.110 Uiso 1 1 calc R . .
O3 O 0.91976(18) 0.98581(14) 0.54560(6) 0.0633(5) Uani 1 1 d . . .
O4 O 1.0992(2) 0.20753(17) 0.55136(6) 0.0762(6) Uani 1 1 d . . .
N3 N 0.4275(2) 0.82418(17) 0.72865(7) 0.0641(6) Uani 1 1 d . . .
N4 N 0.80108(19) 0.55907(16) 0.60140(6) 0.0501(5) Uani 1 1 d . . .
C30 C 0.1271(3) 0.5379(2) 0.82386(8) 0.0631(7) Uani 1 1 d . . .
H30A H 0.0668 0.5221 0.8422 0.076 Uiso 1 1 calc R . .
C31 C 0.1494(3) 0.6476(2) 0.81308(8) 0.0627(7) Uani 1 1 d . . .
H31A H 0.1040 0.7079 0.8239 0.075 Uiso 1 1 calc R . .
C32 C 0.2381(2) 0.6700(2) 0.78645(7) 0.0539(6) Uani 1 1 d . . .
H32A H 0.2533 0.7462 0.7793 0.065 Uiso 1 1 calc R . .
C33 C 0.3054(2) 0.58389(19) 0.76988(6) 0.0450(5) Uani 1 1 d . . .
C34 C 0.2816(2) 0.4728(2) 0.78135(7) 0.0550(6) Uani 1 1 d . . .
H34A H 0.3268 0.4120 0.7709 0.066 Uiso 1 1 calc R . .
C35 C 0.1927(3) 0.4512(2) 0.80792(8) 0.0609(7) Uani 1 1 d . . .
H35A H 0.1767 0.3754 0.8152 0.073 Uiso 1 1 calc R . .
C36 C 0.3976(2) 0.60985(18) 0.74079(6) 0.0446(5) Uani 1 1 d . . .
C37 C 0.4612(2) 0.53228(19) 0.72108(7) 0.0465(5) Uani 1 1 d . . .
H37A H 0.4418 0.4561 0.7271 0.056 Uiso 1 1 calc R . .
C38 C 0.5542(2) 0.54422(18) 0.69220(7) 0.0454(5) Uani 1 1 d . . .
C39 C 0.6116(2) 0.64530(19) 0.68196(7) 0.0485(5) Uani 1 1 d . . .
H39A H 0.5933 0.7127 0.6953 0.058 Uiso 1 1 calc R . .
C40 C 0.6940(2) 0.64944(19) 0.65301(7) 0.0468(5) Uani 1 1 d . . .
H40A H 0.7306 0.7197 0.6467 0.056 Uiso 1 1 calc R . .
C41 C 0.7252(2) 0.55239(18) 0.63265(6) 0.0433(5) Uani 1 1 d . . .
C42 C 0.6733(2) 0.45005(19) 0.64406(7) 0.0493(5) Uani 1 1 d . . .
H42A H 0.6958 0.3819 0.6318 0.059 Uiso 1 1 calc R . .
C43 C 0.5901(2) 0.44675(19) 0.67288(7) 0.0493(5) Uani 1 1 d . . .
H43A H 0.5560 0.3760 0.6799 0.059 Uiso 1 1 calc R . .
C44 C 0.8314(2) 0.66784(19) 0.58600(7) 0.0482(5) Uani 1 1 d . . .
C45 C 0.9325(2) 0.7270(2) 0.59909(7) 0.0566(6) Uani 1 1 d . . .
H45A H 0.9838 0.6949 0.6181 0.068 Uiso 1 1 calc R . .
C46 C 0.9599(2) 0.8327(2) 0.58474(8) 0.0578(6) Uani 1 1 d . . .
H46A H 1.0297 0.8728 0.5939 0.069 Uiso 1 1 calc R . .
C47 C 0.8855(2) 0.8801(2) 0.55697(7) 0.0510(6) Uani 1 1 d . . .
C48 C 0.7853(2) 0.8204(2) 0.54332(8) 0.0576(6) Uani 1 1 d . . .
H48A H 0.7348 0.8515 0.5239 0.069 Uiso 1 1 calc R . .
C49 C 0.7589(2) 0.7150(2) 0.55815(7) 0.0564(6) Uani 1 1 d . . .
H49A H 0.6894 0.6744 0.5489 0.068 Uiso 1 1 calc R . .
C50 C 0.8743(2) 0.46530(19) 0.58985(7) 0.0473(5) Uani 1 1 d . . .
C51 C 0.8816(3) 0.4378(2) 0.55185(7) 0.0566(6) Uani 1 1 d . . .
H51A H 0.8345 0.4792 0.5339 0.068 Uiso 1 1 calc R . .
C52 C 0.9566(3) 0.3509(2) 0.54010(8) 0.0612(7) Uani 1 1 d . . .
H52A H 0.9609 0.3332 0.5141 0.073 Uiso 1 1 calc R . .
C53 C 1.0251(2) 0.2897(2) 0.56573(8) 0.0556(6) Uani 1 1 d . . .
C54 C 1.0167(2) 0.3143(2) 0.60377(7) 0.0538(6) Uani 1 1 d . . .
H54A H 1.0614 0.2708 0.6218 0.065 Uiso 1 1 calc R . .
C55 C 0.9425(2) 0.4028(2) 0.61541(7) 0.0504(6) Uani 1 1 d . . .
H55A H 0.9385 0.4206 0.6414 0.061 Uiso 1 1 calc R . .
C56 C 0.4157(2) 0.7290(2) 0.73388(7) 0.0486(5) Uani 1 1 d . . .
C57 C 0.8536(3) 1.0350(2) 0.51463(8) 0.0675(8) Uani 1 1 d . . .
H57A H 0.8869 1.1102 0.5093 0.101 Uiso 1 1 calc R . .
H57B H 0.7665 1.0415 0.5210 0.101 Uiso 1 1 calc R . .
H57C H 0.8621 0.9868 0.4924 0.101 Uiso 1 1 calc R . .
C58 C 1.1801(4) 0.1524(3) 0.57682(12) 0.1127(15) Uani 1 1 d . . .
H58A H 1.2274 0.0950 0.5633 0.169 Uiso 1 1 calc R . .
H58B H 1.1326 0.1160 0.5967 0.169 Uiso 1 1 calc R . .
H58C H 1.2365 0.2079 0.5881 0.169 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 C18 1.370(3) . ?
O1 C28 1.415(4) . ?
O2 C24 1.367(3) . ?
O2 C29 1.421(4) . ?
N1 C27 1.143(3) . ?
N2 C12 1.388(3) . ?
N2 C15 1.431(3) . ?
N2 C21 1.435(3) . ?
C1 C2 1.377(4) . ?
C1 C6 1.379(4) . ?
C2 C3 1.385(3) . ?
C3 C4 1.392(3) . ?
C4 C5 1.397(3) . ?
C4 C7 1.482(3) . ?
C5 C6 1.387(4) . ?
C7 C8 1.350(3) . ?
C7 C27 1.443(3) . ?
C8 C9 1.455(3) . ?
C9 C10 1.399(3) . ?
C9 C14 1.399(3) . ?
C10 C11 1.375(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.379(3) . ?
C15 C20 1.375(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.386(4) . ?
C17 C18 1.382(4) . ?
C18 C19 1.383(4) . ?
C19 C20 1.394(3) . ?
C21 C26 1.377(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.381(4) . ?
C24 C25 1.384(3) . ?
C25 C26 1.388(3) . ?
O3 C47 1.366(3) . ?
O3 C57 1.430(3) . ?
O4 C53 1.365(3) . ?
O4 C58 1.414(4) . ?
N3 C56 1.148(3) . ?
N4 C41 1.394(3) . ?
N4 C50 1.429(3) . ?
N4 C44 1.437(3) . ?
C30 C35 1.375(4) . ?
C30 C31 1.375(4) . ?
C31 C32 1.386(4) . ?
C32 C33 1.389(3) . ?
C33 C34 1.400(3) . ?
C33 C36 1.481(3) . ?
C34 C35 1.384(4) . ?
C36 C37 1.350(3) . ?
C36 C56 1.444(3) . ?
C37 C38 1.457(3) . ?
C38 C39 1.399(3) . ?
C38 C43 1.400(3) . ?
C39 C40 1.373(3) . ?
C40 C41 1.400(3) . ?
C41 C42 1.397(3) . ?
C42 C43 1.376(3) . ?
C44 C49 1.375(3) . ?
C44 C45 1.380(4) . ?
C45 C46 1.383(3) . ?
C46 C47 1.386(4) . ?
C47 C48 1.382(4) . ?
C48 C49 1.384(3) . ?
C50 C55 1.379(3) . ?
C50 C51 1.392(3) . ?
C51 C52 1.380(4) . ?
C52 C53 1.375(4) . ?
C53 C54 1.387(4) . ?
C54 C55 1.388(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
C18 O1 C28 117.8(2) . . ?
C24 O2 C29 117.5(2) . . ?
C12 N2 C15 121.26(19) . . ?
C12 N2 C21 120.87(19) . . ?
C15 N2 C21 116.59(18) . . ?
C2 C1 C6 118.8(2) . . ?
C1 C2 C3 120.5(2) . . ?
C2 C3 C4 121.2(2) . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 120.3(2) . . ?
C5 C4 C7 121.6(2) . . ?
C6 C5 C4 119.9(2) . . ?
C1 C6 C5 121.5(3) . . ?
C8 C7 C27 120.1(2) . . ?
C8 C7 C4 124.6(2) . . ?
C27 C7 C4 115.3(2) . . ?
C7 C8 C9 131.8(2) . . ?
C10 C9 C14 116.8(2) . . ?
C10 C9 C8 125.9(2) . . ?
C14 C9 C8 117.2(2) . . ?
C11 C10 C9 121.3(2) . . ?
C10 C11 C12 121.3(2) . . ?
N2 C12 C13 121.1(2) . . ?
N2 C12 C11 121.0(2) . . ?
C13 C12 C11 117.9(2) . . ?
C14 C13 C12 120.1(2) . . ?
C13 C14 C9 122.4(2) . . ?
C20 C15 C16 119.2(2) . . ?
C20 C15 N2 119.7(2) . . ?
C16 C15 N2 121.1(2) . . ?
C15 C16 C17 119.9(2) . . ?
C18 C17 C16 120.7(2) . . ?
O1 C18 C17 116.0(2) . . ?
O1 C18 C19 124.3(3) . . ?
C17 C18 C19 119.7(2) . . ?
C18 C19 C20 119.1(2) . . ?
C15 C20 C19 121.3(2) . . ?
C26 C21 C22 118.9(2) . . ?
C26 C21 N2 121.4(2) . . ?
C22 C21 N2 119.6(2) . . ?
C23 C22 C21 120.1(2) . . ?
C24 C23 C22 120.5(2) . . ?
O2 C24 C23 115.7(2) . . ?
O2 C24 C25 124.5(2) . . ?
C23 C24 C25 119.7(2) . . ?
C24 C25 C26 119.3(2) . . ?
C21 C26 C25 121.4(2) . . ?
N1 C27 C7 178.6(3) . . ?
C47 O3 C57 117.5(2) . . ?
C53 O4 C58 117.1(2) . . ?
C41 N4 C50 121.54(19) . . ?
C41 N4 C44 119.64(19) . . ?
C50 N4 C44 116.97(18) . . ?
C35 C30 C31 119.6(2) . . ?
C30 C31 C32 119.8(3) . . ?
C31 C32 C33 121.7(2) . . ?
C32 C33 C34 117.6(2) . . ?
C32 C33 C36 120.6(2) . . ?
C34 C33 C36 121.8(2) . . ?
C35 C34 C33 120.3(2) . . ?
C30 C35 C34 121.0(2) . . ?
C37 C36 C56 120.2(2) . . ?
C37 C36 C33 125.2(2) . . ?
C56 C36 C33 114.6(2) . . ?
C36 C37 C38 131.6(2) . . ?
C39 C38 C43 116.5(2) . . ?
C39 C38 C37 125.6(2) . . ?
C43 C38 C37 117.8(2) . . ?
C40 C39 C38 121.6(2) . . ?
C39 C40 C41 121.5(2) . . ?
N4 C41 C42 121.7(2) . . ?
N4 C41 C40 121.0(2) . . ?
C42 C41 C40 117.3(2) . . ?
C43 C42 C41 120.8(2) . . ?
C42 C43 C38 122.2(2) . . ?
C49 C44 C45 119.0(2) . . ?
C49 C44 N4 120.3(2) . . ?
C45 C44 N4 120.8(2) . . ?
C44 C45 C46 120.5(2) . . ?
C45 C46 C47 120.1(2) . . ?
O3 C47 C48 125.5(2) . . ?
O3 C47 C46 114.9(2) . . ?
C48 C47 C46 119.6(2) . . ?
C47 C48 C49 119.5(2) . . ?
C44 C49 C48 121.3(2) . . ?
C55 C50 C51 118.5(2) . . ?
C55 C50 N4 121.6(2) . . ?
C51 C50 N4 119.9(2) . . ?
C52 C51 C50 120.6(3) . . ?
C53 C52 C51 120.6(2) . . ?
O4 C53 C52 116.4(2) . . ?
O4 C53 C54 124.1(3) . . ?
C52 C53 C54 119.5(2) . . ?
C53 C54 C55 119.7(3) . . ?
C50 C55 C54 121.2(2) . . ?
N3 C56 C36 178.5(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.98
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
####################################################################### 
# 
# 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_ic19154
_database_code_depnum_ccdc_archive 'CCDC 1894256'
loop_
_audit_author_name
_audit_author_address
'Sin-Yu Chen'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-01-29 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H20 N2'
_chemical_formula_weight         372.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'

loop_
_symmetry_equiv_pos_as_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                   16.9323(5)
_cell_length_b                   6.68910(10)
_cell_length_c                   19.8297(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.138(4)
_cell_angle_gamma                90.00
_cell_volume                     2094.83(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5172
_cell_measurement_theta_min      4.2840
_cell_measurement_theta_max      77.3900

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8885
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_sigmaI/netI    0.0236
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         68.00
_reflns_number_total             3800
_reflns_number_gt                3194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0759P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3800
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.1200
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.44928(8) 0.2550(2) 0.81643(6) 0.0416(3) Uani 1 1 d . . .
N2 N 0.37163(12) 0.7147(2) 0.49242(8) 0.0621(4) Uani 1 1 d . . .
C1 C 0.43520(9) 0.2452(2) 0.74245(7) 0.0345(3) Uani 1 1 d . . .
C2 C 0.39336(10) 0.0815(2) 0.70074(8) 0.0385(3) Uani 1 1 d . . .
H2A H 0.3723 -0.0225 0.7223 0.046 Uiso 1 1 calc R . .
C3 C 0.38264(9) 0.0708(2) 0.62848(7) 0.0361(3) Uani 1 1 d . . .
H3A H 0.3557 -0.0433 0.6014 0.043 Uiso 1 1 calc R . .
C4 C 0.41026(8) 0.2233(2) 0.59408(7) 0.0313(3) Uani 1 1 d . . .
C5 C 0.45198(8) 0.3868(2) 0.63626(7) 0.0324(3) Uani 1 1 d . . .
H5A H 0.4720 0.4921 0.6145 0.039 Uiso 1 1 calc R . .
C6 C 0.46438(9) 0.3969(2) 0.70897(7) 0.0340(3) Uani 1 1 d . . .
H6A H 0.4932 0.5085 0.7366 0.041 Uiso 1 1 calc R . .
C7 C 0.39661(8) 0.2008(2) 0.51764(7) 0.0312(3) Uani 1 1 d . . .
H7A H 0.3944 0.0667 0.5012 0.037 Uiso 1 1 calc R . .
C8 C 0.38672(8) 0.3416(2) 0.46673(7) 0.0293(3) Uani 1 1 d . . .
C9 C 0.37986(10) 0.5493(2) 0.48278(8) 0.0383(3) Uani 1 1 d . . .
C10 C 0.37608(8) 0.2979(2) 0.39055(7) 0.0309(3) Uani 1 1 d . . .
C11 C 0.40845(9) 0.1224(2) 0.37273(8) 0.0400(3) Uani 1 1 d . . .
H11A H 0.4371 0.0291 0.4096 0.048 Uiso 1 1 calc R . .
C12 C 0.39906(10) 0.0831(3) 0.30158(9) 0.0490(4) Uani 1 1 d . . .
H12A H 0.4214 -0.0370 0.2900 0.059 Uiso 1 1 calc R . .
C13 C 0.35746(10) 0.2173(3) 0.24723(8) 0.0473(4) Uani 1 1 d . . .
H13A H 0.3517 0.1904 0.1986 0.057 Uiso 1 1 calc R . .
C14 C 0.32454(10) 0.3904(3) 0.26424(8) 0.0457(4) Uani 1 1 d . . .
H14A H 0.2952 0.4822 0.2271 0.055 Uiso 1 1 calc R . .
C15 C 0.33411(9) 0.4309(2) 0.33523(8) 0.0389(3) Uani 1 1 d . . .
H15A H 0.3117 0.5514 0.3464 0.047 Uiso 1 1 calc R . .
C16 C 0.52286(9) 0.3530(2) 0.86480(7) 0.0342(3) Uani 1 1 d . . .
C17 C 0.60245(10) 0.3078(3) 0.86438(8) 0.0451(4) Uani 1 1 d . . .
H17A H 0.6088 0.2085 0.8324 0.054 Uiso 1 1 calc R . .
C18 C 0.67289(10) 0.4078(3) 0.91075(9) 0.0542(5) Uani 1 1 d . . .
H18A H 0.7273 0.3778 0.9099 0.065 Uiso 1 1 calc R . .
C19 C 0.66488(11) 0.5491(3) 0.95770(8) 0.0514(4) Uani 1 1 d . . .
H19A H 0.7134 0.6173 0.9892 0.062 Uiso 1 1 calc R . .
C20 C 0.58610(12) 0.5915(3) 0.95888(9) 0.0514(4) Uani 1 1 d . . .
H20A H 0.5803 0.6874 0.9921 0.062 Uiso 1 1 calc R . .
C21 C 0.51485(10) 0.4957(2) 0.91206(9) 0.0441(4) Uani 1 1 d . . .
H21A H 0.4605 0.5285 0.9125 0.053 Uiso 1 1 calc R . .
C22 C 0.39384(9) 0.1568(2) 0.84556(7) 0.0366(3) Uani 1 1 d . . .
C23 C 0.42579(10) 0.0210(2) 0.90141(8) 0.0427(4) Uani 1 1 d . . .
H23A H 0.4846 -0.0083 0.9200 0.051 Uiso 1 1 calc R . .
C24 C 0.37207(12) -0.0726(3) 0.93027(9) 0.0498(4) Uani 1 1 d . . .
H24A H 0.3943 -0.1656 0.9687 0.060 Uiso 1 1 calc R . .
C25 C 0.28646(12) -0.0311(3) 0.90347(10) 0.0517(4) Uani 1 1 d . . .
H25A H 0.2497 -0.0948 0.9234 0.062 Uiso 1 1 calc R . .
C26 C 0.25468(11) 0.1037(3) 0.84747(10) 0.0540(4) Uani 1 1 d . . .
H26A H 0.1957 0.1321 0.8287 0.065 Uiso 1 1 calc R . .
C27 C 0.30786(10) 0.1980(3) 0.81827(9) 0.0478(4) Uani 1 1 d . . .
H27B H 0.2855 0.2906 0.7797 0.057 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
N1 C1 1.4004(18) . ?
N1 C22 1.4274(19) . ?
N1 C16 1.4283(18) . ?
N2 C9 1.140(2) . ?
C1 C6 1.397(2) . ?
C1 C2 1.401(2) . ?
C2 C3 1.380(2) . ?
C3 C4 1.398(2) . ?
C4 C5 1.4032(19) . ?
C4 C7 1.4563(18) . ?
C5 C6 1.3817(19) . ?
C7 C8 1.3464(19) . ?
C8 C9 1.4393(19) . ?
C8 C10 1.4844(18) . ?
C10 C15 1.392(2) . ?
C10 C11 1.394(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.379(2) . ?
C14 C15 1.385(2) . ?
C16 C21 1.378(2) . ?
C16 C17 1.384(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.367(3) . ?
C19 C20 1.372(3) . ?
C20 C21 1.386(2) . ?
C22 C23 1.383(2) . ?
C22 C27 1.386(2) . ?
C23 C24 1.386(2) . ?
C24 C25 1.380(3) . ?
C25 C26 1.380(3) . ?
C26 C27 1.386(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C22 120.93(12) . . ?
C1 N1 C16 120.18(11) . . ?
C22 N1 C16 118.76(11) . . ?
C6 C1 N1 120.55(13) . . ?
C6 C1 C2 118.52(12) . . ?
N1 C1 C2 120.92(13) . . ?
C3 C2 C1 120.18(13) . . ?
C2 C3 C4 121.82(13) . . ?
C3 C4 C5 117.57(12) . . ?
C3 C4 C7 118.50(12) . . ?
C5 C4 C7 123.91(12) . . ?
C6 C5 C4 120.96(13) . . ?
C5 C6 C1 120.93(12) . . ?
C8 C7 C4 129.66(13) . . ?
C7 C8 C9 120.51(12) . . ?
C7 C8 C10 124.18(12) . . ?
C9 C8 C10 115.17(12) . . ?
N2 C9 C8 176.85(18) . . ?
C15 C10 C11 118.31(13) . . ?
C15 C10 C8 121.08(13) . . ?
C11 C10 C8 120.61(12) . . ?
C12 C11 C10 120.41(14) . . ?
C13 C12 C11 120.57(15) . . ?
C14 C13 C12 119.42(14) . . ?
C13 C14 C15 120.26(15) . . ?
C14 C15 C10 121.02(14) . . ?
C21 C16 C17 119.36(14) . . ?
C21 C16 N1 119.91(13) . . ?
C17 C16 N1 120.73(13) . . ?
C16 C17 C18 119.78(15) . . ?
C19 C18 C17 120.80(15) . . ?
C18 C19 C20 119.35(15) . . ?
C19 C20 C21 120.65(16) . . ?
C16 C21 C20 120.03(15) . . ?
C23 C22 C27 119.74(14) . . ?
C23 C22 N1 120.13(14) . . ?
C27 C22 N1 120.13(14) . . ?
C22 C23 C24 120.11(16) . . ?
C25 C24 C23 120.30(16) . . ?
C26 C25 C24 119.46(15) . . ?
C25 C26 C27 120.67(17) . . ?
C26 C27 C22 119.71(16) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_ic19011
_database_code_depnum_ccdc_archive 'CCDC 1894257'
loop_
_audit_author_name
_audit_author_address
'Sin-Yu Chen'
;National Taiwan University
Taiwan
;
_audit_update_record             
;
2019-01-29 deposited with the CCDC.	2019-04-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H23 Br N2 O2'
_chemical_formula_weight         511.40

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   11.2848(5)
_cell_length_b                   12.4618(5)
_cell_length_c                   17.9846(8)
_cell_angle_alpha                76.742(4)
_cell_angle_beta                 78.065(4)
_cell_angle_gamma                83.320(4)
_cell_volume                     2402.22(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    6565
_cell_measurement_theta_min      3.6350
_cell_measurement_theta_max      75.7590

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent light yellow'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1048
_exptl_absorpt_coefficient_mu    2.560
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.60427
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19911
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0498
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.65
_diffrn_reflns_theta_max         68.00
_reflns_number_total             8741
_reflns_number_gt                6241
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8741
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.28665(4) 0.60007(4) 0.70143(3) 0.06027(14) Uani 1 1 d . . .
O1 O 1.0129(2) 0.39963(19) 0.12001(14) 0.0493(6) Uani 1 1 d . . .
O2 O 0.8323(3) 1.1569(2) 0.04326(17) 0.0640(7) Uani 1 1 d . . .
N1 N 0.2117(3) 0.9643(3) 0.4557(2) 0.0669(10) Uani 1 1 d . . .
N2 N 0.6918(2) 0.7421(2) 0.21103(16) 0.0434(6) Uani 1 1 d . . .
C1 C -0.1423(3) 0.6497(3) 0.63347(19) 0.0442(8) Uani 1 1 d . . .
C2 C -0.0615(3) 0.5740(3) 0.6014(2) 0.0544(9) Uani 1 1 d . . .
H2A H -0.0788 0.4986 0.6127 0.065 Uiso 1 1 calc R . .
C3 C 0.0446(3) 0.6082(3) 0.5529(2) 0.0540(9) Uani 1 1 d . . .
H3A H 0.1006 0.5552 0.5315 0.065 Uiso 1 1 calc R . .
C4 C 0.0721(3) 0.7189(2) 0.53430(18) 0.0388(7) Uani 1 1 d . . .
C5 C -0.0115(3) 0.7919(3) 0.5676(2) 0.0488(8) Uani 1 1 d . . .
H5A H 0.0049 0.8676 0.5563 0.059 Uiso 1 1 calc R . .
C6 C -0.1190(3) 0.7592(3) 0.6171(2) 0.0520(9) Uani 1 1 d . . .
H6A H -0.1751 0.8115 0.6392 0.062 Uiso 1 1 calc R . .
C7 C 0.1850(3) 0.7555(2) 0.48011(18) 0.0375(7) Uani 1 1 d . . .
C8 C 0.2672(3) 0.6887(3) 0.4434(2) 0.0426(7) Uani 1 1 d . . .
H8A H 0.2471 0.6139 0.4561 0.051 Uiso 1 1 calc R . .
C9 C 0.3800(3) 0.7075(3) 0.38827(19) 0.0395(7) Uani 1 1 d . . .
C10 C 0.4363(3) 0.6185(2) 0.3549(2) 0.0429(8) Uani 1 1 d . . .
H10A H 0.4016 0.5491 0.3723 0.052 Uiso 1 1 calc R . .
C11 C 0.5387(3) 0.6275(2) 0.2986(2) 0.0417(7) Uani 1 1 d . . .
H11A H 0.5734 0.5652 0.2775 0.050 Uiso 1 1 calc R . .
C12 C 0.5927(3) 0.7290(2) 0.27188(19) 0.0374(7) Uani 1 1 d . . .
C13 C 0.5415(3) 0.8167(2) 0.30686(19) 0.0401(7) Uani 1 1 d . . .
H13A H 0.5787 0.8849 0.2913 0.048 Uiso 1 1 calc R . .
C14 C 0.4385(3) 0.8068(2) 0.36326(18) 0.0386(7) Uani 1 1 d . . .
H14A H 0.4061 0.8682 0.3859 0.046 Uiso 1 1 calc R . .
C15 C 0.7712(3) 0.6514(2) 0.19022(19) 0.0392(7) Uani 1 1 d . . .
C16 C 0.8219(3) 0.5738(3) 0.24530(19) 0.0426(7) Uani 1 1 d . . .
H16A H 0.8010 0.5794 0.2983 0.051 Uiso 1 1 calc R . .
C17 C 0.9026(3) 0.4880(3) 0.2248(2) 0.0422(7) Uani 1 1 d . . .
H17A H 0.9363 0.4352 0.2634 0.051 Uiso 1 1 calc R . .
C18 C 0.9337(3) 0.4798(2) 0.1472(2) 0.0403(7) Uani 1 1 d . . .
C19 C 0.8841(3) 0.5583(3) 0.09171(19) 0.0426(7) Uani 1 1 d . . .
H19A H 0.9058 0.5539 0.0385 0.051 Uiso 1 1 calc R . .
C20 C 0.8037(3) 0.6424(3) 0.1132(2) 0.0446(8) Uani 1 1 d . . .
H20A H 0.7698 0.6951 0.0746 0.054 Uiso 1 1 calc R . .
C21 C 0.7259(3) 0.8511(2) 0.16983(19) 0.0388(7) Uani 1 1 d . . .
C22 C 0.8395(3) 0.8808(3) 0.1707(2) 0.0427(7) Uani 1 1 d . . .
H22A H 0.8908 0.8312 0.2007 0.051 Uiso 1 1 calc R . .
C23 C 0.8800(3) 0.9820(3) 0.1283(2) 0.0458(8) Uani 1 1 d . . .
H23A H 0.9595 1.0007 0.1279 0.055 Uiso 1 1 calc R . .
C24 C 0.8026(3) 1.0555(3) 0.08655(19) 0.0442(8) Uani 1 1 d . . .
C25 C 0.6870(3) 1.0272(3) 0.0878(2) 0.0468(8) Uani 1 1 d . . .
H25A H 0.6334 1.0783 0.0604 0.056 Uiso 1 1 calc R . .
C26 C 0.6490(3) 0.9245(3) 0.12888(19) 0.0438(7) Uani 1 1 d . . .
H26A H 0.5702 0.9049 0.1288 0.053 Uiso 1 1 calc R . .
C27 C 0.2012(3) 0.8721(3) 0.4663(2) 0.0463(8) Uani 1 1 d . . .
C28 C 1.0765(3) 0.3258(3) 0.1730(2) 0.0556(9) Uani 1 1 d . . .
H28A H 1.1297 0.2729 0.1462 0.083 Uiso 1 1 calc R . .
H28B H 1.0184 0.2857 0.2157 0.083 Uiso 1 1 calc R . .
H28C H 1.1256 0.3674 0.1940 0.083 Uiso 1 1 calc R . .
C29 C 0.9520(4) 1.1873(3) 0.0382(3) 0.0750(13) Uani 1 1 d . . .
H29A H 0.9615 1.2618 0.0060 0.113 Uiso 1 1 calc R . .
H29B H 1.0111 1.1347 0.0148 0.113 Uiso 1 1 calc R . .
H29C H 0.9657 1.1862 0.0905 0.113 Uiso 1 1 calc R . .
Br2 Br 0.76897(4) 0.20795(4) 0.24767(3) 0.07422(17) Uani 1 1 d . . .
O3 O -0.4372(3) -0.2338(2) 0.91262(17) 0.0691(8) Uani 1 1 d . . .
O4 O -0.3876(2) 0.4650(2) 0.93805(17) 0.0594(7) Uani 1 1 d . . .
N3 N 0.3048(3) 0.4345(2) 0.55035(19) 0.0553(8) Uani 1 1 d . . .
N4 N -0.1704(3) 0.1352(2) 0.78003(17) 0.0457(7) Uani 1 1 d . . .
C30 C 0.6406(3) 0.2149(3) 0.3338(2) 0.0514(9) Uani 1 1 d . . .
C31 C 0.5585(4) 0.1341(3) 0.3567(2) 0.0616(11) Uani 1 1 d . . .
H31A H 0.5694 0.0736 0.3315 0.074 Uiso 1 1 calc R . .
C32 C 0.4615(4) 0.1415(3) 0.4158(2) 0.0571(10) Uani 1 1 d . . .
H32A H 0.4052 0.0859 0.4309 0.069 Uiso 1 1 calc R . .
C33 C 0.4440(3) 0.2292(3) 0.45407(19) 0.0426(7) Uani 1 1 d . . .
C34 C 0.5303(3) 0.3084(3) 0.4304(2) 0.0447(8) Uani 1 1 d . . .
H34A H 0.5216 0.3681 0.4563 0.054 Uiso 1 1 calc R . .
C35 C 0.6279(3) 0.3017(3) 0.3703(2) 0.0499(8) Uani 1 1 d . . .
H35A H 0.6851 0.3566 0.3546 0.060 Uiso 1 1 calc R . .
C36 C 0.3356(3) 0.2425(3) 0.51503(19) 0.0414(7) Uani 1 1 d . . .
C37 C 0.2582(3) 0.1625(3) 0.5492(2) 0.0460(8) Uani 1 1 d . . .
H37A H 0.2817 0.0942 0.5335 0.055 Uiso 1 1 calc R . .
C38 C 0.1458(3) 0.1624(3) 0.60564(19) 0.0440(8) Uani 1 1 d . . .
C39 C 0.0995(3) 0.0597(3) 0.6422(2) 0.0484(8) Uani 1 1 d . . .
H39A H 0.1411 -0.0053 0.6277 0.058 Uiso 1 1 calc R . .
C40 C -0.0043(3) 0.0498(3) 0.6985(2) 0.0452(8) Uani 1 1 d . . .
H40A H -0.0318 -0.0214 0.7225 0.054 Uiso 1 1 calc R . .
C41 C -0.0694(3) 0.1426(3) 0.72072(19) 0.0420(7) Uani 1 1 d . . .
C42 C -0.0280(3) 0.2472(3) 0.6807(2) 0.0444(8) Uani 1 1 d . . .
H42A H -0.0733 0.3124 0.6923 0.053 Uiso 1 1 calc R . .
C43 C 0.0763(3) 0.2557(3) 0.6256(2) 0.0461(8) Uani 1 1 d . . .
H43A H 0.1022 0.3270 0.6002 0.055 Uiso 1 1 calc R . .
C44 C -0.2311(3) 0.0344(3) 0.8104(2) 0.0431(7) Uani 1 1 d . . .
C45 C -0.2762(3) -0.0171(3) 0.7637(2) 0.0452(8) Uani 1 1 d . . .
H45A H -0.2605 0.0102 0.7091 0.054 Uiso 1 1 calc R . .
C46 C -0.3448(3) -0.1087(3) 0.7947(2) 0.0492(8) Uani 1 1 d . . .
H46A H -0.3750 -0.1440 0.7616 0.059 Uiso 1 1 calc R . .
C47 C -0.3681(3) -0.1473(3) 0.8746(2) 0.0505(9) Uani 1 1 d . . .
C48 C -0.3210(4) -0.0966(3) 0.9217(2) 0.0554(9) Uani 1 1 d . . .
H48A H -0.3359 -0.1240 0.9763 0.066 Uiso 1 1 calc R . .
C49 C -0.2524(3) -0.0068(3) 0.8902(2) 0.0510(8) Uani 1 1 d . . .
H49A H -0.2198 0.0269 0.9231 0.061 Uiso 1 1 calc R . .
C50 C -0.2207(3) 0.2259(3) 0.81685(19) 0.0423(7) Uani 1 1 d . . .
C51 C -0.3433(3) 0.2546(3) 0.8246(2) 0.0493(8) Uani 1 1 d . . .
H51A H -0.3918 0.2193 0.8013 0.059 Uiso 1 1 calc R . .
C52 C -0.3964(3) 0.3337(3) 0.8654(2) 0.0548(9) Uani 1 1 d . . .
H52A H -0.4817 0.3510 0.8715 0.066 Uiso 1 1 calc R . .
C53 C -0.3269(3) 0.3885(3) 0.8978(2) 0.0451(8) Uani 1 1 d . . .
C54 C -0.2031(3) 0.3633(3) 0.8877(2) 0.0498(8) Uani 1 1 d . . .
H54A H -0.1538 0.4025 0.9076 0.060 Uiso 1 1 calc R . .
C55 C -0.1506(3) 0.2811(3) 0.8486(2) 0.0508(9) Uani 1 1 d . . .
H55A H -0.0657 0.2623 0.8434 0.061 Uiso 1 1 calc R . .
C56 C 0.3158(3) 0.3490(3) 0.5355(2) 0.0451(8) Uani 1 1 d . . .
C57 C -0.5044(4) -0.2764(4) 0.8687(3) 0.0807(15) Uani 1 1 d . . .
H57A H -0.5493 -0.3379 0.9024 0.121 Uiso 1 1 calc R . .
H57B H -0.4487 -0.3028 0.8260 0.121 Uiso 1 1 calc R . .
H57C H -0.5618 -0.2180 0.8473 0.121 Uiso 1 1 calc R . .
C58 C -0.3215(3) 0.5110(3) 0.9813(3) 0.0626(11) Uani 1 1 d . . .
H58A H -0.3753 0.5638 1.0077 0.094 Uiso 1 1 calc R . .
H58B H -0.2536 0.5490 0.9459 0.094 Uiso 1 1 calc R . .
H58C H -0.2900 0.4517 1.0199 0.094 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 C1 1.896(3) . ?
O1 C18 1.368(4) . ?
O1 C28 1.414(4) . ?
O2 C24 1.362(4) . ?
O2 C29 1.425(5) . ?
N1 C27 1.136(4) . ?
N2 C12 1.389(4) . ?
N2 C15 1.428(4) . ?
N2 C21 1.444(4) . ?
C1 C6 1.373(5) . ?
C1 C2 1.373(5) . ?
C2 C3 1.375(5) . ?
C3 C4 1.399(4) . ?
C4 C5 1.376(5) . ?
C4 C7 1.483(4) . ?
C5 C6 1.390(5) . ?
C7 C8 1.345(4) . ?
C7 C27 1.444(4) . ?
C8 C9 1.449(4) . ?
C9 C14 1.407(4) . ?
C9 C10 1.407(4) . ?
C10 C11 1.367(4) . ?
C11 C12 1.408(4) . ?
C12 C13 1.393(4) . ?
C13 C14 1.372(4) . ?
C15 C16 1.382(5) . ?
C15 C20 1.385(5) . ?
C16 C17 1.388(5) . ?
C17 C18 1.391(5) . ?
C18 C19 1.386(5) . ?
C19 C20 1.375(5) . ?
C21 C22 1.378(4) . ?
C21 C26 1.380(5) . ?
C22 C23 1.389(4) . ?
C23 C24 1.392(5) . ?
C24 C25 1.385(5) . ?
C25 C26 1.389(5) . ?
Br2 C30 1.899(3) . ?
O3 C47 1.368(4) . ?
O3 C57 1.421(6) . ?
O4 C53 1.364(4) . ?
O4 C58 1.426(5) . ?
N3 C56 1.144(4) . ?
N4 C41 1.386(4) . ?
N4 C50 1.441(4) . ?
N4 C44 1.442(4) . ?
C30 C35 1.369(5) . ?
C30 C31 1.382(5) . ?
C31 C32 1.370(5) . ?
C32 C33 1.395(5) . ?
C33 C34 1.401(4) . ?
C33 C36 1.486(4) . ?
C34 C35 1.385(5) . ?
C36 C37 1.355(5) . ?
C36 C56 1.438(5) . ?
C37 C38 1.450(4) . ?
C38 C43 1.400(5) . ?
C38 C39 1.404(5) . ?
C39 C40 1.378(5) . ?
C40 C41 1.389(5) . ?
C41 C42 1.416(4) . ?
C42 C43 1.370(5) . ?
C44 C45 1.369(5) . ?
C44 C49 1.389(5) . ?
C45 C46 1.396(5) . ?
C46 C47 1.386(5) . ?
C47 C48 1.381(6) . ?
C48 C49 1.379(5) . ?
C50 C51 1.374(5) . ?
C50 C55 1.385(5) . ?
C51 C52 1.372(5) . ?
C52 C53 1.385(5) . ?
C53 C54 1.379(5) . ?
C54 C55 1.383(5) . ?

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
C18 O1 C28 117.9(3) . . ?
C24 O2 C29 117.5(3) . . ?
C12 N2 C15 122.9(3) . . ?
C12 N2 C21 120.5(2) . . ?
C15 N2 C21 116.3(2) . . ?
C6 C1 C2 120.8(3) . . ?
C6 C1 Br1 120.5(3) . . ?
C2 C1 Br1 118.7(2) . . ?
C1 C2 C3 119.6(3) . . ?
C2 C3 C4 121.7(3) . . ?
C5 C4 C3 116.8(3) . . ?
C5 C4 C7 121.9(3) . . ?
C3 C4 C7 121.3(3) . . ?
C4 C5 C6 122.6(3) . . ?
C1 C6 C5 118.6(3) . . ?
C8 C7 C27 120.4(3) . . ?
C8 C7 C4 124.4(3) . . ?
C27 C7 C4 115.2(3) . . ?
C7 C8 C9 133.1(3) . . ?
C14 C9 C10 116.2(3) . . ?
C14 C9 C8 126.8(3) . . ?
C10 C9 C8 117.0(3) . . ?
C11 C10 C9 122.8(3) . . ?
C10 C11 C12 120.0(3) . . ?
N2 C12 C13 121.1(3) . . ?
N2 C12 C11 120.9(3) . . ?
C13 C12 C11 117.9(3) . . ?
C14 C13 C12 121.5(3) . . ?
C13 C14 C9 121.4(3) . . ?
C16 C15 C20 118.4(3) . . ?
C16 C15 N2 121.3(3) . . ?
C20 C15 N2 120.3(3) . . ?
C15 C16 C17 121.4(3) . . ?
C16 C17 C18 119.5(3) . . ?
O1 C18 C19 116.0(3) . . ?
O1 C18 C17 124.7(3) . . ?
C19 C18 C17 119.3(3) . . ?
C20 C19 C18 120.4(3) . . ?
C19 C20 C15 121.1(3) . . ?
C22 C21 C26 119.7(3) . . ?
C22 C21 N2 118.5(3) . . ?
C26 C21 N2 121.7(3) . . ?
C21 C22 C23 121.1(3) . . ?
C22 C23 C24 119.0(3) . . ?
O2 C24 C25 115.9(3) . . ?
O2 C24 C23 124.2(3) . . ?
C25 C24 C23 119.9(3) . . ?
C24 C25 C26 120.3(3) . . ?
C21 C26 C25 119.9(3) . . ?
N1 C27 C7 178.7(4) . . ?
C47 O3 C57 117.5(3) . . ?
C53 O4 C58 117.6(3) . . ?
C41 N4 C50 123.0(3) . . ?
C41 N4 C44 121.8(3) . . ?
C50 N4 C44 115.2(3) . . ?
C35 C30 C31 120.9(3) . . ?
C35 C30 Br2 119.7(3) . . ?
C31 C30 Br2 119.3(3) . . ?
C32 C31 C30 120.0(3) . . ?
C31 C32 C33 121.1(3) . . ?
C32 C33 C34 117.4(3) . . ?
C32 C33 C36 122.1(3) . . ?
C34 C33 C36 120.4(3) . . ?
C35 C34 C33 121.6(3) . . ?
C30 C35 C34 118.9(3) . . ?
C37 C36 C56 121.0(3) . . ?
C37 C36 C33 123.9(3) . . ?
C56 C36 C33 115.1(3) . . ?
C36 C37 C38 131.6(3) . . ?
C43 C38 C39 116.3(3) . . ?
C43 C38 C37 126.1(3) . . ?
C39 C38 C37 117.5(3) . . ?
C40 C39 C38 122.3(3) . . ?
C39 C40 C41 120.9(3) . . ?
N4 C41 C40 122.3(3) . . ?
N4 C41 C42 120.3(3) . . ?
C40 C41 C42 117.4(3) . . ?
C43 C42 C41 121.1(3) . . ?
C42 C43 C38 121.9(3) . . ?
C45 C44 C49 119.2(3) . . ?
C45 C44 N4 122.0(3) . . ?
C49 C44 N4 118.7(3) . . ?
C44 C45 C46 121.5(3) . . ?
C47 C46 C45 118.8(4) . . ?
O3 C47 C48 115.4(3) . . ?
O3 C47 C46 124.8(4) . . ?
C48 C47 C46 119.8(3) . . ?
C49 C48 C47 120.7(3) . . ?
C48 C49 C44 120.0(4) . . ?
C51 C50 C55 118.9(3) . . ?
C51 C50 N4 119.0(3) . . ?
C55 C50 N4 122.0(3) . . ?
C52 C51 C50 120.8(3) . . ?
C51 C52 C53 120.6(3) . . ?
O4 C53 C54 124.5(3) . . ?
O4 C53 C52 116.5(3) . . ?
C54 C53 C52 119.0(3) . . ?
C53 C54 C55 120.1(3) . . ?
C54 C55 C50 120.6(3) . . ?
N3 C56 C36 177.3(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.602
_refine_diff_density_rms         0.056
