# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bp78
_database_code_depnum_ccdc_archive 'CCDC 1027764'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C26 H17 N O3), C H2 Cl2'
_chemical_formula_sum            'C53 H36 Cl2 N2 O6'
_chemical_formula_weight         867.74

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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   '	P na21'
_symmetry_space_group_name_Hall  '	P 2c -2n'

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

_cell_length_a                   26.5772(4)
_cell_length_b                   11.8718(2)
_cell_length_c                   12.8742(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4062.06(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22319
_cell_measurement_theta_min      3.3230
_cell_measurement_theta_max      76.2355

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1996
_exptl_crystal_size_mid          0.1398
_exptl_crystal_size_min          0.0937
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1800
_exptl_absorpt_coefficient_mu    1.914
_exptl_absorpt_correction_T_min  0.784
_exptl_absorpt_correction_T_max  0.869
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            40982
_diffrn_reflns_av_R_equivalents  0.0151
_diffrn_reflns_av_sigmaI/netI    0.0645
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         72.90
_reflns_number_total             7997
_reflns_number_gt                7850
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_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)+(0.0593P)²+1.4146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.244(10)
_refine_ls_number_reflns         7997
_refine_ls_number_parameters     571
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0961
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.735642(18) 0.13473(4) 0.18103(4) 0.03727(12) Uani 1 1 d . . .
Cl2 Cl 0.75126(2) 0.37774(4) 0.19115(7) 0.05003(15) Uani 1 1 d . . .
O52 O 0.48520(5) 0.30205(10) 0.26970(10) 0.0223(3) Uani 1 1 d . . .
O22 O 0.47846(5) 0.81057(10) 0.59406(10) 0.0236(3) Uani 1 1 d . . .
O14 O 0.58724(5) 0.76583(11) 0.61651(10) 0.0239(3) Uani 1 1 d . . .
H14 H 0.5585 0.7528 0.6410 0.036 Uiso 1 1 calc R . .
N1 N 0.51091(6) 0.91457(13) 0.45688(12) 0.0227(3) Uani 1 1 d . . .
O44 O 0.59349(5) 0.26787(11) 0.26760(10) 0.0232(3) Uani 1 1 d . . .
H44 H 0.5660 0.2572 0.2371 0.035 Uiso 1 1 calc R . .
O30 O 0.66349(6) 1.24110(13) 0.83335(14) 0.0396(4) Uani 1 1 d . . .
O60 O 0.66995(6) 0.75107(13) 0.06668(13) 0.0375(4) Uani 1 1 d . . .
C34 C 0.56196(7) 0.50167(16) 0.57510(15) 0.0256(4) Uani 1 1 d . . .
H34 H 0.5788 0.5245 0.6366 0.031 Uiso 1 1 calc R . .
C50 C 0.42413(7) 0.41257(14) 0.37016(14) 0.0224(4) Uani 1 1 d . . .
C51 C 0.47388(7) 0.36503(14) 0.34191(14) 0.0205(3) Uani 1 1 d . . .
C53 C 0.57857(7) 0.49951(14) 0.32010(14) 0.0209(4) Uani 1 1 d . . .
C36 C 0.56207(7) 0.40962(14) 0.39948(14) 0.0207(3) Uani 1 1 d . . .
C49 C 0.37696(7) 0.39094(16) 0.32822(15) 0.0253(4) Uani 1 1 d . . .
H49 H 0.3726 0.3389 0.2729 0.030 Uiso 1 1 calc R . .
C38 C 0.67431(8) 0.38825(16) 0.57647(16) 0.0283(4) Uani 1 1 d . . .
H38 H 0.6741 0.4442 0.6292 0.034 Uiso 1 1 calc R . .
C7 C 0.63886(7) 0.86226(15) 0.37995(15) 0.0253(4) Uani 1 1 d . . .
N31 N 0.50747(6) 0.40932(12) 0.41214(12) 0.0207(3) Uani 1 1 d . . .
C41 C 0.67410(7) 0.21960(17) 0.42292(16) 0.0275(4) Uani 1 1 d . . .
H41 H 0.6739 0.1616 0.3721 0.033 Uiso 1 1 calc R . .
C56 C 0.61057(7) 0.66162(15) 0.17694(15) 0.0241(4) Uani 1 1 d . . .
C48 C 0.33639(7) 0.44887(17) 0.37070(16) 0.0288(4) Uani 1 1 d . . .
H48 H 0.3036 0.4366 0.3438 0.035 Uiso 1 1 calc R . .
C12 C 0.63436(7) 0.78044(15) 0.45751(14) 0.0226(4) Uani 1 1 d . . .
C6 C 0.56464(7) 0.90837(15) 0.47865(14) 0.0218(4) Uani 1 1 d . . .
C59 C 0.62736(8) 0.74343(16) 0.09807(17) 0.0292(4) Uani 1 1 d . . .
H59 H 0.6030 0.7935 0.0701 0.035 Uiso 1 1 calc R . .
C33 C 0.51081(8) 0.53711(16) 0.55655(15) 0.0253(4) Uani 1 1 d . . .
H33 H 0.4960 0.5945 0.5979 0.030 Uiso 1 1 calc R . .
C15 C 0.44006(7) 1.00974(15) 0.40647(15) 0.0249(4) Uani 1 1 d . . .
C21 C 0.47304(7) 0.87724(15) 0.52165(14) 0.0227(4) Uani 1 1 d . . .
C35 C 0.58574(7) 0.43626(15) 0.50525(14) 0.0230(4) Uani 1 1 d . . .
C28 C 0.62998(7) 1.00546(16) 0.59323(15) 0.0250(4) Uani 1 1 d . . .
H28 H 0.6544 0.9554 0.5655 0.030 Uiso 1 1 calc R . .
C57 C 0.64534(7) 0.58859(15) 0.22194(15) 0.0243(4) Uani 1 1 d . . .
H57 H 0.6799 0.5937 0.2038 0.029 Uiso 1 1 calc R . .
C24 C 0.54499(8) 1.07382(16) 0.59978(16) 0.0273(4) Uani 1 1 d . . .
H24 H 0.5110 1.0713 0.5769 0.033 Uiso 1 1 calc R . .
C54 C 0.54426(7) 0.57332(16) 0.27529(16) 0.0254(4) Uani 1 1 d . . .
H54 H 0.5097 0.5689 0.2934 0.030 Uiso 1 1 calc R . .
C11 C 0.67321(7) 0.70587(16) 0.47757(16) 0.0262(4) Uani 1 1 d . . .
H11 H 0.6700 0.6500 0.5300 0.031 Uiso 1 1 calc R . .
C43 C 0.58450(7) 0.29041(15) 0.37361(14) 0.0221(4) Uani 1 1 d . . .
H43 H 0.5616 0.2312 0.4021 0.027 Uiso 1 1 calc R . .
C32 C 0.48441(7) 0.48778(15) 0.47997(14) 0.0224(4) Uani 1 1 d . . .
C4 C 0.57399(8) 0.99579(16) 0.30180(15) 0.0275(4) Uani 1 1 d . . .
H4 H 0.5937 1.0144 0.2427 0.033 Uiso 1 1 calc R . .
C23 C 0.57983(7) 0.99804(15) 0.55961(14) 0.0221(4) Uani 1 1 d . . .
C26 C 0.60875(7) 1.15899(15) 0.70703(15) 0.0255(4) Uani 1 1 d . . .
C20 C 0.42716(7) 0.93690(15) 0.48765(15) 0.0244(4) Uani 1 1 d . . .
C45 C 0.43142(7) 0.48894(15) 0.45184(15) 0.0234(4) Uani 1 1 d . . .
C46 C 0.39029(8) 0.54624(16) 0.49440(16) 0.0279(4) Uani 1 1 d . . .
H46 H 0.3945 0.5979 0.5501 0.033 Uiso 1 1 calc R . .
C19 C 0.37844(7) 0.92939(16) 0.52504(16) 0.0270(4) Uani 1 1 d . . .
H19 H 0.3700 0.8791 0.5797 0.032 Uiso 1 1 calc R . .
C18 C 0.34217(8) 0.99825(17) 0.47962(17) 0.0310(4) Uani 1 1 d . . .
H18 H 0.3085 0.9959 0.5041 0.037 Uiso 1 1 calc R . .
C58 C 0.62953(7) 0.50866(16) 0.29302(16) 0.0245(4) Uani 1 1 d . . .
H58 H 0.6534 0.4594 0.3238 0.029 Uiso 1 1 calc R . .
C55 C 0.56035(7) 0.65360(16) 0.20407(16) 0.0278(4) Uani 1 1 d . . .
H55 H 0.5366 0.7035 0.1737 0.033 Uiso 1 1 calc R . .
C10 C 0.71716(8) 0.71458(18) 0.41928(17) 0.0323(4) Uani 1 1 d . . .
H10 H 0.7443 0.6646 0.4325 0.039 Uiso 1 1 calc R . .
C16 C 0.40326(8) 1.07766(16) 0.36012(15) 0.0293(4) Uani 1 1 d . . .
H16 H 0.4114 1.1267 0.3043 0.035 Uiso 1 1 calc R . .
C47 C 0.34326(8) 0.52491(17) 0.45230(17) 0.0311(4) Uani 1 1 d . . .
H47 H 0.3148 0.5632 0.4798 0.037 Uiso 1 1 calc R . .
C8 C 0.68253(8) 0.86978(17) 0.32061(16) 0.0309(4) Uani 1 1 d . . .
H8 H 0.6854 0.9243 0.2669 0.037 Uiso 1 1 calc R . .
C27 C 0.64412(7) 1.08449(15) 0.66588(16) 0.0262(4) Uani 1 1 d . . .
H27 H 0.6782 1.0883 0.6881 0.031 Uiso 1 1 calc R . .
C13 C 0.58333(7) 0.78740(15) 0.50961(14) 0.0220(4) Uani 1 1 d . . .
H13 H 0.5605 0.7302 0.4776 0.026 Uiso 1 1 calc R . .
C3 C 0.52352(8) 1.03852(16) 0.31114(15) 0.0266(4) Uani 1 1 d . . .
H3 H 0.5118 1.0957 0.2656 0.032 Uiso 1 1 calc R . .
C42 C 0.63300(7) 0.28977(15) 0.43511(15) 0.0233(4) Uani 1 1 d . . .
C37 C 0.63277(7) 0.37395(15) 0.51131(15) 0.0242(4) Uani 1 1 d . . .
C2 C 0.49318(8) 0.99622(16) 0.38545(15) 0.0249(4) Uani 1 1 d . . .
C5 C 0.59318(7) 0.92958(15) 0.37662(15) 0.0241(4) Uani 1 1 d . . .
C61 C 0.71019(8) 0.26933(17) 0.15316(18) 0.0338(5) Uani 1 1 d . . .
H61A H 0.7036 0.2753 0.0777 0.041 Uiso 1 1 calc R . .
H61B H 0.6777 0.2781 0.1900 0.041 Uiso 1 1 calc R . .
C25 C 0.55963(8) 1.15370(16) 0.67351(18) 0.0309(4) Uani 1 1 d . . .
H25 H 0.5355 1.2048 0.7007 0.037 Uiso 1 1 calc R . .
C9 C 0.72167(8) 0.79599(19) 0.34162(17) 0.0327(4) Uani 1 1 d . . .
H9 H 0.7519 0.8009 0.3027 0.039 Uiso 1 1 calc R . .
C17 C 0.35505(8) 1.07095(16) 0.39800(16) 0.0311(4) Uani 1 1 d . . .
H17 H 0.3297 1.1169 0.3680 0.037 Uiso 1 1 calc R . .
C29 C 0.62276(8) 1.23900(17) 0.79044(18) 0.0326(5) Uani 1 1 d . . .
H29 H 0.5982 1.2924 0.8119 0.039 Uiso 1 1 calc R . .
C39 C 0.71549(8) 0.31999(18) 0.56295(17) 0.0321(4) Uani 1 1 d . . .
H39 H 0.7442 0.3301 0.6059 0.039 Uiso 1 1 calc R . .
C40 C 0.71587(8) 0.23585(18) 0.48688(17) 0.0319(4) Uani 1 1 d . . .
H40 H 0.7447 0.1895 0.4787 0.038 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C61 1.772(2) . ?
Cl2 C61 1.757(2) . ?
O52 C51 1.230(2) . ?
O22 C21 1.231(2) . ?
O14 C13 1.404(2) . ?
O14 H14 0.8400 . ?
N1 C21 1.380(2) . ?
N1 C2 1.417(2) . ?
N1 C6 1.457(2) . ?
O44 C43 1.411(2) . ?
O44 H44 0.8400 . ?
O30 C29 1.216(3) . ?
O60 C59 1.205(3) . ?
C34 C35 1.346(3) . ?
C34 C33 1.443(3) . ?
C34 H34 0.9500 . ?
C50 C49 1.389(3) . ?
C50 C45 1.402(3) . ?
C50 C51 1.483(3) . ?
C51 N31 1.375(2) . ?
C53 C54 1.390(3) . ?
C53 C58 1.403(3) . ?
C53 C36 1.541(2) . ?
C36 N31 1.460(2) . ?
C36 C35 1.533(2) . ?
C36 C43 1.571(2) . ?
C49 C48 1.391(3) . ?
C49 H49 0.9500 . ?
C38 C39 1.373(3) . ?
C38 C37 1.397(3) . ?
C38 H38 0.9500 . ?
C7 C8 1.392(3) . ?
C7 C12 1.398(3) . ?
C7 C5 1.454(3) . ?
N31 C32 1.416(2) . ?
C41 C42 1.383(3) . ?
C41 C40 1.396(3) . ?
C41 H41 0.9500 . ?
C56 C55 1.383(3) . ?
C56 C57 1.393(3) . ?
C56 C59 1.474(3) . ?
C48 C47 1.397(3) . ?
C48 H48 0.9500 . ?
C12 C11 1.385(3) . ?
C12 C13 1.515(3) . ?
C6 C5 1.538(3) . ?
C6 C23 1.543(3) . ?
C6 C13 1.571(2) . ?
C59 H59 0.9500 . ?
C33 C32 1.344(3) . ?
C33 H33 0.9500 . ?
C15 C20 1.399(3) . ?
C15 C16 1.401(3) . ?
C15 C2 1.446(3) . ?
C21 C20 1.476(3) . ?
C35 C37 1.455(3) . ?
C28 C27 1.377(3) . ?
C28 C23 1.404(3) . ?
C28 H28 0.9500 . ?
C57 C58 1.384(3) . ?
C57 H57 0.9500 . ?
C24 C23 1.391(3) . ?
C24 C25 1.397(3) . ?
C24 H24 0.9500 . ?
C54 C55 1.390(3) . ?
C54 H54 0.9500 . ?
C11 C10 1.392(3) . ?
C11 H11 0.9500 . ?
C43 C42 1.513(3) . ?
C43 H43 1.0000 . ?
C32 C45 1.454(3) . ?
C4 C5 1.344(3) . ?
C4 C3 1.439(3) . ?
C4 H4 0.9500 . ?
C26 C25 1.376(3) . ?
C26 C27 1.395(3) . ?
C26 C29 1.481(3) . ?
C20 C19 1.384(3) . ?
C45 C46 1.399(3) . ?
C46 C47 1.386(3) . ?
C46 H46 0.9500 . ?
C19 C18 1.393(3) . ?
C19 H19 0.9500 . ?
C18 C17 1.402(3) . ?
C18 H18 0.9500 . ?
C58 H58 0.9500 . ?
C55 H55 0.9500 . ?
C10 C9 1.396(3) . ?
C10 H10 0.9500 . ?
C16 C17 1.373(3) . ?
C16 H16 0.9500 . ?
C47 H47 0.9500 . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C27 H27 0.9500 . ?
C13 H13 1.0000 . ?
C3 C2 1.348(3) . ?
C3 H3 0.9500 . ?
C42 C37 1.400(3) . ?
C61 H61A 0.9900 . ?
C61 H61B 0.9900 . ?
C25 H25 0.9500 . ?
C9 H9 0.9500 . ?
C17 H17 0.9500 . ?
C29 H29 0.9500 . ?
C39 C40 1.399(3) . ?
C39 H39 0.9500 . ?
C40 H40 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O14 H14 109.5 . . ?
C21 N1 C2 111.67(16) . . ?
C21 N1 C6 125.61(16) . . ?
C2 N1 C6 119.04(15) . . ?
C43 O44 H44 109.5 . . ?
C35 C34 C33 120.01(18) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C49 C50 C45 122.42(17) . . ?
C49 C50 C51 129.72(17) . . ?
C45 C50 C51 107.87(16) . . ?
O52 C51 N31 124.78(17) . . ?
O52 C51 C50 129.40(17) . . ?
N31 C51 C50 105.78(15) . . ?
C54 C53 C58 118.78(17) . . ?
C54 C53 C36 121.68(16) . . ?
C58 C53 C36 119.54(16) . . ?
N31 C36 C35 108.00(15) . . ?
N31 C36 C53 111.00(14) . . ?
C35 C36 C53 109.24(14) . . ?
N31 C36 C43 113.48(14) . . ?
C35 C36 C43 102.61(14) . . ?
C53 C36 C43 112.03(14) . . ?
C50 C49 C48 117.09(18) . . ?
C50 C49 H49 121.5 . . ?
C48 C49 H49 121.5 . . ?
C39 C38 C37 118.82(19) . . ?
C39 C38 H38 120.6 . . ?
C37 C38 H38 120.6 . . ?
C8 C7 C12 120.52(18) . . ?
C8 C7 C5 130.13(18) . . ?
C12 C7 C5 109.35(17) . . ?
C51 N31 C32 112.08(15) . . ?
C51 N31 C36 124.94(15) . . ?
C32 N31 C36 119.82(15) . . ?
C42 C41 C40 118.6(2) . . ?
C42 C41 H41 120.7 . . ?
C40 C41 H41 120.7 . . ?
C55 C56 C57 119.49(17) . . ?
C55 C56 C59 120.76(17) . . ?
C57 C56 C59 119.70(17) . . ?
C49 C48 C47 120.93(19) . . ?
C49 C48 H48 119.5 . . ?
C47 C48 H48 119.5 . . ?
C11 C12 C7 120.90(18) . . ?
C11 C12 C13 128.31(17) . . ?
C7 C12 C13 110.79(16) . . ?
N1 C6 C5 108.11(15) . . ?
N1 C6 C23 110.57(15) . . ?
C5 C6 C23 109.57(14) . . ?
N1 C6 C13 113.88(14) . . ?
C5 C6 C13 102.15(15) . . ?
C23 C6 C13 112.11(15) . . ?
O60 C59 C56 124.40(19) . . ?
O60 C59 H59 117.8 . . ?
C56 C59 H59 117.8 . . ?
C32 C33 C34 119.08(18) . . ?
C32 C33 H33 120.5 . . ?
C34 C33 H33 120.5 . . ?
C20 C15 C16 120.18(19) . . ?
C20 C15 C2 108.08(16) . . ?
C16 C15 C2 131.73(19) . . ?
O22 C21 N1 125.35(17) . . ?
O22 C21 C20 129.00(18) . . ?
N1 C21 C20 105.61(16) . . ?
C34 C35 C37 131.39(18) . . ?
C34 C35 C36 121.33(17) . . ?
C37 C35 C36 107.18(15) . . ?
C27 C28 C23 120.74(18) . . ?
C27 C28 H28 119.6 . . ?
C23 C28 H28 119.6 . . ?
C58 C57 C56 120.01(17) . . ?
C58 C57 H57 120.0 . . ?
C56 C57 H57 120.0 . . ?
C23 C24 C25 120.43(18) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C53 C54 C55 120.29(17) . . ?
C53 C54 H54 119.9 . . ?
C55 C54 H54 119.9 . . ?
C12 C11 C10 118.54(18) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
O44 C43 C42 111.16(15) . . ?
O44 C43 C36 116.10(15) . . ?
C42 C43 C36 102.52(14) . . ?
O44 C43 H43 108.9 . . ?
C42 C43 H43 108.9 . . ?
C36 C43 H43 108.9 . . ?
C33 C32 N31 120.86(18) . . ?
C33 C32 C45 133.15(18) . . ?
N31 C32 C45 105.77(15) . . ?
C5 C4 C3 120.01(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C24 C23 C28 118.47(17) . . ?
C24 C23 C6 121.55(17) . . ?
C28 C23 C6 119.98(17) . . ?
C25 C26 C27 119.42(18) . . ?
C25 C26 C29 119.66(18) . . ?
C27 C26 C29 120.82(18) . . ?
C19 C20 C15 121.92(18) . . ?
C19 C20 C21 129.68(18) . . ?
C15 C20 C21 108.40(17) . . ?
C46 C45 C50 120.00(18) . . ?
C46 C45 C32 131.58(18) . . ?
C50 C45 C32 108.34(16) . . ?
C47 C46 C45 117.56(19) . . ?
C47 C46 H46 121.2 . . ?
C45 C46 H46 121.2 . . ?
C20 C19 C18 117.63(19) . . ?
C20 C19 H19 121.2 . . ?
C18 C19 H19 121.2 . . ?
C19 C18 C17 120.46(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C57 C58 C53 120.72(17) . . ?
C57 C58 H58 119.6 . . ?
C53 C58 H58 119.6 . . ?
C56 C55 C54 120.71(17) . . ?
C56 C55 H55 119.6 . . ?
C54 C55 H55 119.6 . . ?
C11 C10 C9 120.63(19) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C17 C16 C15 117.82(19) . . ?
C17 C16 H16 121.1 . . ?
C15 C16 H16 121.1 . . ?
C46 C47 C48 122.00(18) . . ?
C46 C47 H47 119.0 . . ?
C48 C47 H47 119.0 . . ?
C9 C8 C7 118.54(19) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C28 C27 C26 120.39(18) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
O14 C13 C12 110.96(15) . . ?
O14 C13 C6 116.04(15) . . ?
C12 C13 C6 102.74(14) . . ?
O14 C13 H13 108.9 . . ?
C12 C13 H13 108.9 . . ?
C6 C13 H13 108.9 . . ?
C2 C3 C4 119.05(18) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C41 C42 C37 120.85(18) . . ?
C41 C42 C43 128.08(18) . . ?
C37 C42 C43 111.07(16) . . ?
C38 C37 C42 120.27(18) . . ?
C38 C37 C35 130.51(18) . . ?
C42 C37 C35 109.20(16) . . ?
C3 C2 N1 121.09(18) . . ?
C3 C2 C15 132.47(18) . . ?
N1 C2 C15 106.21(16) . . ?
C4 C5 C7 131.27(18) . . ?
C4 C5 C6 121.39(18) . . ?
C7 C5 C6 107.26(16) . . ?
Cl2 C61 Cl1 111.53(11) . . ?
Cl2 C61 H61A 109.3 . . ?
Cl1 C61 H61A 109.3 . . ?
Cl2 C61 H61B 109.3 . . ?
Cl1 C61 H61B 109.3 . . ?
H61A C61 H61B 108.0 . . ?
C26 C25 C24 120.53(18) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C8 C9 C10 120.9(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C16 C17 C18 121.98(18) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
O30 C29 C26 124.50(19) . . ?
O30 C29 H29 117.7 . . ?
C26 C29 H29 117.7 . . ?
C38 C39 C40 121.06(19) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C41 C40 C39 120.40(19) . . ?
C41 C40 H40 119.8 . . ?
C39 C40 H40 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C49 C50 C51 O52 6.2(3) . . . . ?
C45 C50 C51 O52 -173.80(18) . . . . ?
C49 C50 C51 N31 -176.09(18) . . . . ?
C45 C50 C51 N31 3.93(19) . . . . ?
C54 C53 C36 N31 4.4(2) . . . . ?
C58 C53 C36 N31 -176.53(16) . . . . ?
C54 C53 C36 C35 -114.62(19) . . . . ?
C58 C53 C36 C35 64.5(2) . . . . ?
C54 C53 C36 C43 132.38(18) . . . . ?
C58 C53 C36 C43 -48.5(2) . . . . ?
C45 C50 C49 C48 0.1(3) . . . . ?
C51 C50 C49 C48 -179.88(18) . . . . ?
O52 C51 N31 C32 174.00(16) . . . . ?
C50 C51 N31 C32 -3.87(19) . . . . ?
O52 C51 N31 C36 14.3(3) . . . . ?
C50 C51 N31 C36 -163.58(15) . . . . ?
C35 C36 N31 C51 -164.79(16) . . . . ?
C53 C36 N31 C51 75.5(2) . . . . ?
C43 C36 N31 C51 -51.7(2) . . . . ?
C35 C36 N31 C32 36.9(2) . . . . ?
C53 C36 N31 C32 -82.79(19) . . . . ?
C43 C36 N31 C32 149.99(16) . . . . ?
C50 C49 C48 C47 -0.3(3) . . . . ?
C8 C7 C12 C11 0.5(3) . . . . ?
C5 C7 C12 C11 -179.18(17) . . . . ?
C8 C7 C12 C13 -178.83(17) . . . . ?
C5 C7 C12 C13 1.5(2) . . . . ?
C21 N1 C6 C5 165.32(16) . . . . ?
C2 N1 C6 C5 -38.2(2) . . . . ?
C21 N1 C6 C23 -74.7(2) . . . . ?
C2 N1 C6 C23 81.8(2) . . . . ?
C21 N1 C6 C13 52.6(2) . . . . ?
C2 N1 C6 C13 -150.93(16) . . . . ?
C55 C56 C59 O60 -175.9(2) . . . . ?
C57 C56 C59 O60 1.6(3) . . . . ?
C35 C34 C33 C32 12.3(3) . . . . ?
C2 N1 C21 O22 -176.29(17) . . . . ?
C6 N1 C21 O22 -18.3(3) . . . . ?
C2 N1 C21 C20 1.6(2) . . . . ?
C6 N1 C21 C20 159.60(16) . . . . ?
C33 C34 C35 C37 -168.29(18) . . . . ?
C33 C34 C35 C36 7.5(3) . . . . ?
N31 C36 C35 C34 -30.4(2) . . . . ?
C53 C36 C35 C34 90.4(2) . . . . ?
C43 C36 C35 C34 -150.56(17) . . . . ?
N31 C36 C35 C37 146.25(14) . . . . ?
C53 C36 C35 C37 -92.91(17) . . . . ?
C43 C36 C35 C37 26.12(17) . . . . ?
C55 C56 C57 C58 0.1(3) . . . . ?
C59 C56 C57 C58 -177.48(18) . . . . ?
C58 C53 C54 C55 0.8(3) . . . . ?
C36 C53 C54 C55 179.89(17) . . . . ?
C7 C12 C11 C10 0.5(3) . . . . ?
C13 C12 C11 C10 179.70(18) . . . . ?
N31 C36 C43 O44 97.01(18) . . . . ?
C35 C36 C43 O44 -146.73(15) . . . . ?
C53 C36 C43 O44 -29.7(2) . . . . ?
N31 C36 C43 C42 -141.62(15) . . . . ?
C35 C36 C43 C42 -25.36(17) . . . . ?
C53 C36 C43 C42 91.70(17) . . . . ?
C34 C33 C32 N31 -5.6(3) . . . . ?
C34 C33 C32 C45 168.14(19) . . . . ?
C51 N31 C32 C33 177.59(16) . . . . ?
C36 N31 C32 C33 -21.5(2) . . . . ?
C51 N31 C32 C45 2.3(2) . . . . ?
C36 N31 C32 C45 163.22(15) . . . . ?
C25 C24 C23 C28 -1.3(3) . . . . ?
C25 C24 C23 C6 179.57(18) . . . . ?
C27 C28 C23 C24 1.3(3) . . . . ?
C27 C28 C23 C6 -179.59(17) . . . . ?
N1 C6 C23 C24 -2.0(2) . . . . ?
C5 C6 C23 C24 117.02(19) . . . . ?
C13 C6 C23 C24 -130.29(19) . . . . ?
N1 C6 C23 C28 178.89(16) . . . . ?
C5 C6 C23 C28 -62.0(2) . . . . ?
C13 C6 C23 C28 50.6(2) . . . . ?
C16 C15 C20 C19 -0.2(3) . . . . ?
C2 C15 C20 C19 -179.26(17) . . . . ?
C16 C15 C20 C21 -179.50(17) . . . . ?
C2 C15 C20 C21 1.5(2) . . . . ?
O22 C21 C20 C19 -3.3(3) . . . . ?
N1 C21 C20 C19 178.90(19) . . . . ?
O22 C21 C20 C15 175.90(18) . . . . ?
N1 C21 C20 C15 -1.9(2) . . . . ?
C49 C50 C45 C46 0.3(3) . . . . ?
C51 C50 C45 C46 -179.73(16) . . . . ?
C49 C50 C45 C32 177.44(17) . . . . ?
C51 C50 C45 C32 -2.57(19) . . . . ?
C33 C32 C45 C46 2.6(4) . . . . ?
N31 C32 C45 C46 177.00(19) . . . . ?
C33 C32 C45 C50 -174.11(19) . . . . ?
N31 C32 C45 C50 0.29(19) . . . . ?
C50 C45 C46 C47 -0.5(3) . . . . ?
C32 C45 C46 C47 -176.87(19) . . . . ?
C15 C20 C19 C18 -0.6(3) . . . . ?
C21 C20 C19 C18 178.46(18) . . . . ?
C20 C19 C18 C17 0.9(3) . . . . ?
C56 C57 C58 C53 0.4(3) . . . . ?
C54 C53 C58 C57 -0.9(3) . . . . ?
C36 C53 C58 C57 179.98(17) . . . . ?
C57 C56 C55 C54 -0.2(3) . . . . ?
C59 C56 C55 C54 177.34(19) . . . . ?
C53 C54 C55 C56 -0.2(3) . . . . ?
C12 C11 C10 C9 -0.7(3) . . . . ?
C20 C15 C16 C17 0.9(3) . . . . ?
C2 C15 C16 C17 179.62(19) . . . . ?
C45 C46 C47 C48 0.3(3) . . . . ?
C49 C48 C47 C46 0.1(3) . . . . ?
C12 C7 C8 C9 -1.3(3) . . . . ?
C5 C7 C8 C9 178.3(2) . . . . ?
C23 C28 C27 C26 -0.3(3) . . . . ?
C25 C26 C27 C28 -0.7(3) . . . . ?
C29 C26 C27 C28 175.74(18) . . . . ?
C11 C12 C13 O14 38.1(3) . . . . ?
C7 C12 C13 O14 -142.61(15) . . . . ?
C11 C12 C13 C6 162.76(19) . . . . ?
C7 C12 C13 C6 -17.96(19) . . . . ?
N1 C6 C13 O14 -96.49(19) . . . . ?
C5 C6 C13 O14 147.22(15) . . . . ?
C23 C6 C13 O14 30.0(2) . . . . ?
N1 C6 C13 C12 142.28(16) . . . . ?
C5 C6 C13 C12 25.98(17) . . . . ?
C23 C6 C13 C12 -91.24(17) . . . . ?
C5 C4 C3 C2 -11.4(3) . . . . ?
C40 C41 C42 C37 -1.3(3) . . . . ?
C40 C41 C42 C43 178.24(18) . . . . ?
O44 C43 C42 C41 -37.8(3) . . . . ?
C36 C43 C42 C41 -162.45(19) . . . . ?
O44 C43 C42 C37 141.79(15) . . . . ?
C36 C43 C42 C37 17.09(19) . . . . ?
C39 C38 C37 C42 1.3(3) . . . . ?
C39 C38 C37 C35 -177.14(19) . . . . ?
C41 C42 C37 C38 0.0(3) . . . . ?
C43 C42 C37 C38 -179.60(16) . . . . ?
C41 C42 C37 C35 178.72(17) . . . . ?
C43 C42 C37 C35 -0.9(2) . . . . ?
C34 C35 C37 C38 -21.8(3) . . . . ?
C36 C35 C37 C38 162.03(19) . . . . ?
C34 C35 C37 C42 159.68(19) . . . . ?
C36 C35 C37 C42 -16.54(19) . . . . ?
C4 C3 C2 N1 2.9(3) . . . . ?
C4 C3 C2 C15 -170.88(19) . . . . ?
C21 N1 C2 C3 -175.96(18) . . . . ?
C6 N1 C2 C3 24.5(3) . . . . ?
C21 N1 C2 C15 -0.8(2) . . . . ?
C6 N1 C2 C15 -160.35(16) . . . . ?
C20 C15 C2 C3 173.9(2) . . . . ?
C16 C15 C2 C3 -4.9(4) . . . . ?
C20 C15 C2 N1 -0.5(2) . . . . ?
C16 C15 C2 N1 -179.36(19) . . . . ?
C3 C4 C5 C7 169.31(19) . . . . ?
C3 C4 C5 C6 -6.8(3) . . . . ?
C8 C7 C5 C4 20.2(3) . . . . ?
C12 C7 C5 C4 -160.2(2) . . . . ?
C8 C7 C5 C6 -163.27(19) . . . . ?
C12 C7 C5 C6 16.4(2) . . . . ?
N1 C6 C5 C4 30.2(2) . . . . ?
C23 C6 C5 C4 -90.4(2) . . . . ?
C13 C6 C5 C4 150.59(17) . . . . ?
N1 C6 C5 C7 -146.79(15) . . . . ?
C23 C6 C5 C7 92.64(17) . . . . ?
C13 C6 C5 C7 -26.39(18) . . . . ?
C27 C26 C25 C24 0.7(3) . . . . ?
C29 C26 C25 C24 -175.82(19) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C11 C10 C9 C8 -0.1(3) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C19 C18 C17 C16 -0.2(3) . . . . ?
C25 C26 C29 O30 171.2(2) . . . . ?
C27 C26 C29 O30 -5.2(3) . . . . ?
C37 C38 C39 C40 -1.3(3) . . . . ?
C42 C41 C40 C39 1.3(3) . . . . ?
C38 C39 C40 C41 0.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        72.90
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_bpxx
_database_code_depnum_ccdc_archive 'CCDC 1027765'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H17 N O2'
_chemical_formula_sum            'C25 H17 N O2'
_chemical_formula_weight         363.40

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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                   10.6552(3)
_cell_length_b                   8.1691(2)
_cell_length_c                   20.6721(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.472(3)
_cell_angle_gamma                90.00
_cell_volume                     1742.28(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    6072
_cell_measurement_theta_min      4.2817
_cell_measurement_theta_max      76.1788

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2276
_exptl_crystal_size_mid          0.1760
_exptl_crystal_size_min          0.0948
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.702
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      109.95(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_measurement_method       'omega scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9695
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         70.13
_reflns_number_total             3235
_reflns_number_gt                3092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_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)+(0.0411P)²+0.9513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3235
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0910
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
O14 O 0.19305(8) 0.40206(11) 0.09486(4) 0.0214(2) Uani 1 1 d . . .
H14 H 0.1262 0.4305 0.0659 0.032 Uiso 1 1 calc R . .
O22 O 0.07552(8) 0.47120(11) -0.04593(4) 0.0205(2) Uani 1 1 d . . .
N1 N 0.26491(10) 0.34542(13) -0.05489(5) 0.0192(2) Uani 1 1 d . . .
C15 C 0.22271(13) 0.31966(15) -0.16876(6) 0.0214(3) Uani 1 1 d . . .
C3 C 0.43648(13) 0.21427(16) -0.09169(7) 0.0234(3) Uani 1 1 d . . .
H3 H 0.4692 0.1658 -0.1259 0.028 Uiso 1 1 calc R . .
C20 C 0.11829(13) 0.40037(15) -0.15329(6) 0.0206(3) Uani 1 1 d . . .
C21 C 0.14424(12) 0.41416(14) -0.07996(6) 0.0183(3) Uani 1 1 d . . .
C6 C 0.31152(12) 0.28397(15) 0.01316(6) 0.0184(3) Uani 1 1 d . . .
C2 C 0.31779(12) 0.28387(15) -0.10636(6) 0.0213(3) Uani 1 1 d . . .
C23 C 0.24589(11) 0.12019(15) 0.02132(6) 0.0183(3) Uani 1 1 d . . .
C5 C 0.45806(12) 0.25670(15) 0.02617(6) 0.0202(3) Uani 1 1 d . . .
C16 C 0.22197(13) 0.29057(16) -0.23533(7) 0.0250(3) Uani 1 1 d . . .
H16 H 0.2921 0.2359 -0.2468 0.030 Uiso 1 1 calc R . .
C27 C 0.21091(13) -0.10423(16) 0.09127(7) 0.0232(3) Uani 1 1 d . . .
H27 H 0.2244 -0.1522 0.1343 0.028 Uiso 1 1 calc R . .
C12 C 0.42495(13) 0.38404(15) 0.12118(6) 0.0213(3) Uani 1 1 d . . .
C17 C 0.11588(14) 0.34378(17) -0.28427(7) 0.0277(3) Uani 1 1 d . . .
H17 H 0.1136 0.3248 -0.3299 0.033 Uiso 1 1 calc R . .
C24 C 0.17008(12) 0.03728(16) -0.03372(6) 0.0213(3) Uani 1 1 d . . .
H24 H 0.1547 0.0854 -0.0768 0.026 Uiso 1 1 calc R . .
C28 C 0.26591(12) 0.04719(16) 0.08416(6) 0.0213(3) Uani 1 1 d . . .
H28 H 0.3174 0.1012 0.1223 0.026 Uiso 1 1 calc R . .
C11 C 0.45491(13) 0.43651(17) 0.18715(7) 0.0250(3) Uani 1 1 d . . .
H11 H 0.3948 0.4997 0.2037 0.030 Uiso 1 1 calc R . .
C9 C 0.66419(14) 0.30491(19) 0.20401(7) 0.0311(3) Uani 1 1 d . . .
H9 H 0.7457 0.2780 0.2330 0.037 Uiso 1 1 calc R . .
C7 C 0.51458(12) 0.29404(16) 0.09644(7) 0.0220(3) Uani 1 1 d . . .
C8 C 0.63547(13) 0.25450(17) 0.13780(7) 0.0273(3) Uani 1 1 d . . .
H8 H 0.6969 0.1944 0.1210 0.033 Uiso 1 1 calc R . .
C4 C 0.51299(13) 0.21447(16) -0.02339(7) 0.0228(3) Uani 1 1 d . . .
H4 H 0.6020 0.1848 -0.0134 0.027 Uiso 1 1 calc R . .
C26 C 0.13663(12) -0.18546(16) 0.03604(7) 0.0232(3) Uani 1 1 d . . .
H26 H 0.0996 -0.2890 0.0411 0.028 Uiso 1 1 calc R . .
C25 C 0.11678(12) -0.11473(16) -0.02632(7) 0.0238(3) Uani 1 1 d . . .
H25 H 0.0664 -0.1703 -0.0644 0.029 Uiso 1 1 calc R . .
C18 C 0.01227(14) 0.42445(18) -0.26826(7) 0.0280(3) Uani 1 1 d . . .
H18 H -0.0589 0.4601 -0.3030 0.034 Uiso 1 1 calc R . .
C19 C 0.01200(13) 0.45335(16) -0.20194(7) 0.0248(3) Uani 1 1 d . . .
H19 H -0.0585 0.5074 -0.1905 0.030 Uiso 1 1 calc R . .
C13 C 0.30184(12) 0.41340(15) 0.06775(6) 0.0197(3) Uani 1 1 d . . .
H13 H 0.3049 0.5257 0.0489 0.024 Uiso 1 1 calc R . .
C10 C 0.57429(14) 0.39489(18) 0.22838(7) 0.0300(3) Uani 1 1 d . . .
H10 H 0.5954 0.4280 0.2739 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
O14 C13 1.4109(15) . ?
O14 H14 0.8400 . ?
O22 C21 1.2272(15) . ?
N1 C21 1.3799(16) . ?
N1 C2 1.4147(16) . ?
N1 C6 1.4589(16) . ?
C15 C16 1.3945(18) . ?
C15 C20 1.3974(18) . ?
C15 C2 1.4570(19) . ?
C3 C2 1.3502(19) . ?
C3 C4 1.4432(19) . ?
C3 H3 0.9500 . ?
C20 C19 1.3828(19) . ?
C20 C21 1.4756(17) . ?
C6 C5 1.5330(17) . ?
C6 C23 1.5383(17) . ?
C6 C13 1.5685(17) . ?
C23 C24 1.3951(18) . ?
C23 C28 1.3964(18) . ?
C5 C4 1.3456(18) . ?
C5 C7 1.4590(18) . ?
C16 C17 1.385(2) . ?
C16 H16 0.9500 . ?
C27 C26 1.3851(19) . ?
C27 C28 1.3922(18) . ?
C27 H27 0.9500 . ?
C12 C11 1.3884(18) . ?
C12 C7 1.3995(18) . ?
C12 C13 1.5080(18) . ?
C17 C18 1.395(2) . ?
C17 H17 0.9500 . ?
C24 C25 1.3898(18) . ?
C24 H24 0.9500 . ?
C28 H28 0.9500 . ?
C11 C10 1.385(2) . ?
C11 H11 0.9500 . ?
C9 C8 1.388(2) . ?
C9 C10 1.397(2) . ?
C9 H9 0.9500 . ?
C7 C8 1.3943(19) . ?
C8 H8 0.9500 . ?
C4 H4 0.9500 . ?
C26 C25 1.3799(19) . ?
C26 H26 0.9500 . ?
C25 H25 0.9500 . ?
C18 C19 1.3919(19) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C13 H13 1.0000 . ?
C10 H10 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O14 H14 109.5 . . ?
C21 N1 C2 111.78(10) . . ?
C21 N1 C6 124.25(10) . . ?
C2 N1 C6 119.95(10) . . ?
C16 C15 C20 119.85(12) . . ?
C16 C15 C2 132.13(12) . . ?
C20 C15 C2 108.02(11) . . ?
C2 C3 C4 119.18(12) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C19 C20 C15 122.38(12) . . ?
C19 C20 C21 129.22(12) . . ?
C15 C20 C21 108.40(11) . . ?
O22 C21 N1 124.94(11) . . ?
O22 C21 C20 129.24(12) . . ?
N1 C21 C20 105.81(10) . . ?
N1 C6 C5 107.78(10) . . ?
N1 C6 C23 110.52(10) . . ?
C5 C6 C23 108.99(10) . . ?
N1 C6 C13 113.21(10) . . ?
C5 C6 C13 102.65(10) . . ?
C23 C6 C13 113.20(10) . . ?
C3 C2 N1 120.50(12) . . ?
C3 C2 C15 133.50(12) . . ?
N1 C2 C15 105.97(11) . . ?
C24 C23 C28 118.29(11) . . ?
C24 C23 C6 121.28(11) . . ?
C28 C23 C6 120.37(11) . . ?
C4 C5 C7 131.43(12) . . ?
C4 C5 C6 121.43(12) . . ?
C7 C5 C6 107.05(10) . . ?
C17 C16 C15 118.01(12) . . ?
C17 C16 H16 121.0 . . ?
C15 C16 H16 121.0 . . ?
C26 C27 C28 120.50(12) . . ?
C26 C27 H27 119.8 . . ?
C28 C27 H27 119.8 . . ?
C11 C12 C7 120.72(12) . . ?
C11 C12 C13 127.93(12) . . ?
C7 C12 C13 111.35(11) . . ?
C16 C17 C18 121.65(12) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C25 C24 C23 120.88(12) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C27 C28 C23 120.48(12) . . ?
C27 C28 H28 119.8 . . ?
C23 C28 H28 119.8 . . ?
C10 C11 C12 118.62(13) . . ?
C10 C11 H11 120.7 . . ?
C12 C11 H11 120.7 . . ?
C8 C9 C10 120.62(13) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C8 C7 C12 120.52(12) . . ?
C8 C7 C5 130.57(12) . . ?
C12 C7 C5 108.91(11) . . ?
C9 C8 C7 118.56(13) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C5 C4 C3 119.88(12) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C25 C26 C27 119.48(12) . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C26 C25 C24 120.36(12) . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C19 C18 C17 120.70(13) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C18 117.41(12) . . ?
C20 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?
O14 C13 C12 110.44(10) . . ?
O14 C13 C6 116.73(10) . . ?
C12 C13 C6 102.61(10) . . ?
O14 C13 H13 108.9 . . ?
C12 C13 H13 108.9 . . ?
C6 C13 H13 108.9 . . ?
C11 C10 C9 120.94(13) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?

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
C16 C15 C20 C19 0.2(2) . . . . ?
C2 C15 C20 C19 179.10(12) . . . . ?
C16 C15 C20 C21 179.86(11) . . . . ?
C2 C15 C20 C21 -1.23(14) . . . . ?
C2 N1 C21 O22 177.35(12) . . . . ?
C6 N1 C21 O22 20.06(19) . . . . ?
C2 N1 C21 C20 -1.64(13) . . . . ?
C6 N1 C21 C20 -158.94(11) . . . . ?
C19 C20 C21 O22 2.5(2) . . . . ?
C15 C20 C21 O22 -177.17(12) . . . . ?
C19 C20 C21 N1 -178.60(13) . . . . ?
C15 C20 C21 N1 1.77(13) . . . . ?
C21 N1 C6 C5 -166.63(11) . . . . ?
C2 N1 C6 C5 37.82(14) . . . . ?
C21 N1 C6 C23 74.37(14) . . . . ?
C2 N1 C6 C23 -81.19(13) . . . . ?
C21 N1 C6 C13 -53.81(15) . . . . ?
C2 N1 C6 C13 150.63(11) . . . . ?
C4 C3 C2 N1 -4.67(19) . . . . ?
C4 C3 C2 C15 172.68(13) . . . . ?
C21 N1 C2 C3 178.92(12) . . . . ?
C6 N1 C2 C3 -22.69(18) . . . . ?
C21 N1 C2 C15 0.92(14) . . . . ?
C6 N1 C2 C15 159.31(10) . . . . ?
C16 C15 C2 C3 1.4(3) . . . . ?
C20 C15 C2 C3 -177.37(14) . . . . ?
C16 C15 C2 N1 178.98(13) . . . . ?
C20 C15 C2 N1 0.25(14) . . . . ?
N1 C6 C23 C24 9.48(15) . . . . ?
C5 C6 C23 C24 -108.79(13) . . . . ?
C13 C6 C23 C24 137.67(12) . . . . ?
N1 C6 C23 C28 -173.44(11) . . . . ?
C5 C6 C23 C28 68.28(14) . . . . ?
C13 C6 C23 C28 -45.26(15) . . . . ?
N1 C6 C5 C4 -30.90(16) . . . . ?
C23 C6 C5 C4 89.08(14) . . . . ?
C13 C6 C5 C4 -150.65(12) . . . . ?
N1 C6 C5 C7 146.02(10) . . . . ?
C23 C6 C5 C7 -94.00(12) . . . . ?
C13 C6 C5 C7 26.28(12) . . . . ?
C20 C15 C16 C17 -0.01(19) . . . . ?
C2 C15 C16 C17 -178.61(13) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C28 C23 C24 C25 -0.56(18) . . . . ?
C6 C23 C24 C25 176.58(11) . . . . ?
C26 C27 C28 C23 0.67(19) . . . . ?
C24 C23 C28 C27 -0.21(18) . . . . ?
C6 C23 C28 C27 -177.37(11) . . . . ?
C7 C12 C11 C10 -1.39(19) . . . . ?
C13 C12 C11 C10 179.59(12) . . . . ?
C11 C12 C7 C8 0.41(19) . . . . ?
C13 C12 C7 C8 179.58(12) . . . . ?
C11 C12 C7 C5 -179.60(11) . . . . ?
C13 C12 C7 C5 -0.43(14) . . . . ?
C4 C5 C7 C8 -20.4(2) . . . . ?
C6 C5 C7 C8 163.11(13) . . . . ?
C4 C5 C7 C12 159.62(14) . . . . ?
C6 C5 C7 C12 -16.88(14) . . . . ?
C10 C9 C8 C7 -0.7(2) . . . . ?
C12 C7 C8 C9 0.6(2) . . . . ?
C5 C7 C8 C9 -179.35(13) . . . . ?
C7 C5 C4 C3 -168.20(13) . . . . ?
C6 C5 C4 C3 7.88(19) . . . . ?
C2 C3 C4 C5 11.72(19) . . . . ?
C28 C27 C26 C25 -0.35(19) . . . . ?
C27 C26 C25 C24 -0.42(19) . . . . ?
C23 C24 C25 C26 0.88(19) . . . . ?
C16 C17 C18 C19 -0.4(2) . . . . ?
C15 C20 C19 C18 -0.5(2) . . . . ?
C21 C20 C19 C18 179.96(12) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C11 C12 C13 O14 -38.99(17) . . . . ?
C7 C12 C13 O14 141.91(11) . . . . ?
C11 C12 C13 C6 -164.10(12) . . . . ?
C7 C12 C13 C6 16.80(13) . . . . ?
N1 C6 C13 O14 97.91(12) . . . . ?
C5 C6 C13 O14 -146.19(10) . . . . ?
C23 C6 C13 O14 -28.87(15) . . . . ?
N1 C6 C13 C12 -141.21(10) . . . . ?
C5 C6 C13 C12 -25.31(12) . . . . ?
C23 C6 C13 C12 92.01(11) . . . . ?
C12 C11 C10 C9 1.3(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        70.13
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_vm952
_database_code_depnum_ccdc_archive 'CCDC 1027766'
_audit_update_record             
;
2014-10-06 deposited with the CCDC.
2014-12-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H17 N O2'
_chemical_formula_sum            'C21 H17 N O2'
_chemical_formula_weight         315.36

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           triclinic
_symmetry_space_group_name_H-M   'P -1'

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

_cell_length_a                   8.3902(4)
_cell_length_b                   9.4235(5)
_cell_length_c                   10.5655(5)
_cell_angle_alpha                68.634(5)
_cell_angle_beta                 86.055(4)
_cell_angle_gamma                83.059(4)
_cell_volume                     771.97(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    4931
_cell_measurement_theta_min      4.4916
_cell_measurement_theta_max      76.1755

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1943
_exptl_crystal_size_mid          0.1465
_exptl_crystal_size_min          0.0893
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             332
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.916
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4508
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8377
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0862
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.50
_diffrn_reflns_theta_max         76.17
_reflns_number_total             3099
_reflns_number_gt                2686
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SIR_92 (Altomare et al., 1994)'
_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)+(0.1036P)²+0.2821P] 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         3099
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0636
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
O14 O 0.80639(15) 0.45303(17) 0.19077(14) 0.0408(4) Uani 1 1 d . . .
O22 O 0.61055(16) 0.25601(15) 0.38499(14) 0.0404(4) Uani 1 1 d . . .
N1 N 0.42087(17) 0.45866(18) 0.27928(15) 0.0330(4) Uani 1 1 d . . .
C12 C 0.6881(2) 0.6643(2) 0.00126(18) 0.0335(4) Uani 1 1 d . . .
C5 C 0.4330(2) 0.7055(2) 0.09200(17) 0.0314(4) Uani 1 1 d . . .
C4 C 0.2715(2) 0.7358(2) 0.09978(18) 0.0343(4) Uani 1 1 d . . .
C15 C 0.1946(2) 0.3671(2) 0.39958(18) 0.0349(4) Uani 1 1 d . . .
C20 C 0.3237(2) 0.2542(2) 0.44397(18) 0.0351(4) Uani 1 1 d . . .
C6 C 0.5255(2) 0.5762(2) 0.20393(18) 0.0327(4) Uani 1 1 d . . .
C8 C 0.5455(2) 0.9098(2) -0.12613(19) 0.0377(4) Uani 1 1 d . . .
H8 H 0.4535 0.9825 -0.1394 0.045 Uiso 1 1 calc R . .
C21 C 0.4709(2) 0.3150(2) 0.36959(18) 0.0340(4) Uani 1 1 d . . .
C24 C 0.5911(2) 0.6380(2) 0.30399(19) 0.0378(4) Uani 1 1 d . . .
H24B H 0.5019 0.6862 0.3440 0.057 Uiso 1 1 calc R . .
H24A H 0.6656 0.7138 0.2555 0.057 Uiso 1 1 calc R . .
H24C H 0.6478 0.5532 0.3763 0.057 Uiso 1 1 calc R . .
C7 C 0.5505(2) 0.7703(2) -0.01643(18) 0.0337(4) Uani 1 1 d . . .
C10 C 0.8118(2) 0.8343(3) -0.1969(2) 0.0412(5) Uani 1 1 d . . .
H10 H 0.9003 0.8573 -0.2594 0.049 Uiso 1 1 calc R . .
C9 C 0.6770(3) 0.9401(2) -0.2152(2) 0.0419(5) Uani 1 1 d . . .
H9 H 0.6749 1.0347 -0.2898 0.050 Uiso 1 1 calc R . .
C11 C 0.8191(2) 0.6951(2) -0.08828(19) 0.0383(4) Uani 1 1 d . . .
H11 H 0.9115 0.6230 -0.0758 0.046 Uiso 1 1 calc R . .
C3 C 0.1829(2) 0.6334(2) 0.21110(19) 0.0351(4) Uani 1 1 d . . .
H3 H 0.0724 0.6610 0.2259 0.042 Uiso 1 1 calc R . .
C2 C 0.2552(2) 0.4992(2) 0.29410(18) 0.0331(4) Uani 1 1 d . . .
C13 C 0.6632(2) 0.5203(2) 0.12147(18) 0.0334(4) Uani 1 1 d . . .
H13 H 0.6227 0.4451 0.0881 0.040 Uiso 1 1 calc R . .
C16 C 0.0396(2) 0.3374(3) 0.4523(2) 0.0414(5) Uani 1 1 d . . .
H16 H -0.0491 0.4132 0.4227 0.050 Uiso 1 1 calc R . .
C18 C 0.1492(3) 0.0820(3) 0.5923(2) 0.0449(5) Uani 1 1 d . . .
H18 H 0.1316 -0.0155 0.6581 0.054 Uiso 1 1 calc R . .
C19 C 0.3031(2) 0.1113(2) 0.54082(18) 0.0390(4) Uani 1 1 d . . .
H19 H 0.3917 0.0356 0.5710 0.047 Uiso 1 1 calc R . .
C23 C 0.1774(2) 0.8636(2) -0.0075(2) 0.0430(5) Uani 1 1 d . . .
H23A H 0.1915 0.9615 0.0010 0.065 Uiso 1 1 calc R . .
H23B H 0.0633 0.8474 0.0044 0.065 Uiso 1 1 calc R . .
H23C H 0.2160 0.8654 -0.0976 0.065 Uiso 1 1 calc R . .
C17 C 0.0190(3) 0.1949(3) 0.5483(2) 0.0471(5) Uani 1 1 d . . .
H17 H -0.0854 0.1727 0.5854 0.057 Uiso 1 1 calc R . .
H14 H 0.777(3) 0.376(3) 0.263(3) 0.055(7) Uiso 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O14 C13 1.407(2) . ?
O14 H14 0.89(3) . ?
O22 C21 1.229(2) . ?
N1 C21 1.377(2) . ?
N1 C2 1.410(2) . ?
N1 C6 1.459(2) . ?
C12 C11 1.386(3) . ?
C12 C7 1.407(3) . ?
C12 C13 1.508(3) . ?
C5 C4 1.354(2) . ?
C5 C7 1.462(3) . ?
C5 C6 1.527(2) . ?
C4 C3 1.447(3) . ?
C4 C23 1.502(2) . ?
C15 C20 1.397(3) . ?
C15 C16 1.398(3) . ?
C15 C2 1.455(3) . ?
C20 C19 1.386(3) . ?
C20 C21 1.477(3) . ?
C6 C24 1.538(2) . ?
C6 C13 1.556(2) . ?
C8 C9 1.386(3) . ?
C8 C7 1.398(3) . ?
C8 H8 0.9500 . ?
C24 H24B 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24C 0.9800 . ?
C10 C9 1.388(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C11 H11 0.9500 . ?
C3 C2 1.347(3) . ?
C3 H3 0.9500 . ?
C13 H13 1.0000 . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C18 C19 1.385(3) . ?
C18 C17 1.403(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O14 H14 104.8(17) . . ?
C21 N1 C2 112.28(15) . . ?
C21 N1 C6 125.47(15) . . ?
C2 N1 C6 120.03(15) . . ?
C11 C12 C7 121.28(18) . . ?
C11 C12 C13 128.47(17) . . ?
C7 C12 C13 110.18(15) . . ?
C4 C5 C7 131.44(17) . . ?
C4 C5 C6 122.00(16) . . ?
C7 C5 C6 106.40(15) . . ?
C5 C4 C3 118.67(16) . . ?
C5 C4 C23 123.26(17) . . ?
C3 C4 C23 117.88(16) . . ?
C20 C15 C16 120.23(18) . . ?
C20 C15 C2 107.75(16) . . ?
C16 C15 C2 131.92(18) . . ?
C19 C20 C15 121.62(18) . . ?
C19 C20 C21 129.68(18) . . ?
C15 C20 C21 108.69(16) . . ?
N1 C6 C5 110.36(14) . . ?
N1 C6 C24 108.54(15) . . ?
C5 C6 C24 110.56(15) . . ?
N1 C6 C13 113.60(15) . . ?
C5 C6 C13 102.05(14) . . ?
C24 C6 C13 111.63(14) . . ?
C9 C8 C7 118.89(18) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O22 C21 N1 125.70(17) . . ?
O22 C21 C20 129.04(17) . . ?
N1 C21 C20 105.22(15) . . ?
C6 C24 H24B 109.5 . . ?
C6 C24 H24A 109.5 . . ?
H24B C24 H24A 109.5 . . ?
C6 C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
C8 C7 C12 119.57(17) . . ?
C8 C7 C5 131.72(17) . . ?
C12 C7 C5 108.71(16) . . ?
C9 C10 C11 120.93(18) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C8 C9 C10 120.98(19) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C12 C11 C10 118.34(19) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C2 C3 C4 120.78(17) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C2 N1 120.93(17) . . ?
C3 C2 C15 132.88(17) . . ?
N1 C2 C15 105.96(15) . . ?
O14 C13 C12 112.08(15) . . ?
O14 C13 C6 116.18(15) . . ?
C12 C13 C6 102.51(14) . . ?
O14 C13 H13 108.6 . . ?
C12 C13 H13 108.6 . . ?
C6 C13 H13 108.6 . . ?
C17 C16 C15 118.14(19) . . ?
C17 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C19 C18 C17 120.70(19) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C20 117.98(19) . . ?
C18 C19 H19 121.0 . . ?
C20 C19 H19 121.0 . . ?
C4 C23 H23A 109.5 . . ?
C4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C17 C18 121.33(19) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 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
C7 C5 C4 C3 168.83(19) . . . . ?
C6 C5 C4 C3 -6.0(3) . . . . ?
C7 C5 C4 C23 -6.1(3) . . . . ?
C6 C5 C4 C23 178.99(18) . . . . ?
C16 C15 C20 C19 -0.3(3) . . . . ?
C2 C15 C20 C19 -177.26(16) . . . . ?
C16 C15 C20 C21 178.61(17) . . . . ?
C2 C15 C20 C21 1.7(2) . . . . ?
C21 N1 C6 C5 167.60(16) . . . . ?
C2 N1 C6 C5 -30.7(2) . . . . ?
C21 N1 C6 C24 -71.1(2) . . . . ?
C2 N1 C6 C24 90.61(18) . . . . ?
C21 N1 C6 C13 53.7(2) . . . . ?
C2 N1 C6 C13 -144.58(15) . . . . ?
C4 C5 C6 N1 24.9(2) . . . . ?
C7 C5 C6 N1 -151.09(15) . . . . ?
C4 C5 C6 C24 -95.2(2) . . . . ?
C7 C5 C6 C24 88.82(17) . . . . ?
C4 C5 C6 C13 145.96(17) . . . . ?
C7 C5 C6 C13 -30.03(18) . . . . ?
C2 N1 C21 O22 -174.60(18) . . . . ?
C6 N1 C21 O22 -11.7(3) . . . . ?
C2 N1 C21 C20 3.2(2) . . . . ?
C6 N1 C21 C20 166.17(16) . . . . ?
C19 C20 C21 O22 -6.4(3) . . . . ?
C15 C20 C21 O22 174.76(19) . . . . ?
C19 C20 C21 N1 175.82(18) . . . . ?
C15 C20 C21 N1 -3.0(2) . . . . ?
C9 C8 C7 C12 0.0(3) . . . . ?
C9 C8 C7 C5 -179.33(19) . . . . ?
C11 C12 C7 C8 -0.1(3) . . . . ?
C13 C12 C7 C8 -177.31(16) . . . . ?
C11 C12 C7 C5 179.32(17) . . . . ?
C13 C12 C7 C5 2.2(2) . . . . ?
C4 C5 C7 C8 22.1(3) . . . . ?
C6 C5 C7 C8 -162.45(19) . . . . ?
C4 C5 C7 C12 -157.3(2) . . . . ?
C6 C5 C7 C12 18.2(2) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C11 C10 C9 C8 -0.3(3) . . . . ?
C7 C12 C11 C10 0.1(3) . . . . ?
C13 C12 C11 C10 176.66(17) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C5 C4 C3 C2 -9.4(3) . . . . ?
C23 C4 C3 C2 165.83(18) . . . . ?
C4 C3 C2 N1 3.4(3) . . . . ?
C4 C3 C2 C15 -170.27(18) . . . . ?
C21 N1 C2 C3 -177.45(17) . . . . ?
C6 N1 C2 C3 18.6(3) . . . . ?
C21 N1 C2 C15 -2.3(2) . . . . ?
C6 N1 C2 C15 -166.26(15) . . . . ?
C20 C15 C2 C3 174.6(2) . . . . ?
C16 C15 C2 C3 -1.9(4) . . . . ?
C20 C15 C2 N1 0.3(2) . . . . ?
C16 C15 C2 N1 -176.2(2) . . . . ?
C11 C12 C13 O14 36.9(3) . . . . ?
C7 C12 C13 O14 -146.16(16) . . . . ?
C11 C12 C13 C6 162.22(18) . . . . ?
C7 C12 C13 C6 -20.87(18) . . . . ?
N1 C6 C13 O14 -88.59(19) . . . . ?
C5 C6 C13 O14 152.63(16) . . . . ?
C24 C6 C13 O14 34.5(2) . . . . ?
N1 C6 C13 C12 148.85(14) . . . . ?
C5 C6 C13 C12 30.08(17) . . . . ?
C24 C6 C13 C12 -88.01(16) . . . . ?
C20 C15 C16 C17 0.1(3) . . . . ?
C2 C15 C16 C17 176.17(19) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C15 C20 C19 C18 0.6(3) . . . . ?
C21 C20 C19 C18 -178.07(19) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C19 C18 C17 C16 0.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.958
_diffrn_reflns_theta_full        76.17
_diffrn_measured_fraction_theta_full 0.958
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.055

# start Validation Reply Form
_vrf_PLAT029_vm952               
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.958 Note  
RESPONSE: Crystal was seen to be shifted at the end of experiment.
Data collection runs collected after the problem occurs were then excluded
from data reduction, leading to an uncomplete coverage.
;
# end Validation Reply Form
