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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1457745'
_audit_update_record             
;
2016-03-04 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H21 N O2 '
_chemical_formula_sum            'C25 H21 N O2 '
_chemical_formula_weight         367.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'C2/c  '

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

_cell_length_a                   21.5950(12)
_cell_length_b                   11.9233(6)
_cell_length_c                   18.1759(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.106(2)
_cell_angle_gamma                90.00
_cell_volume                     3828.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296
_cell_measurement_reflns_used    4454
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9243
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4389
_reflns_number_gt                3105
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0564P)²+1.5832P] 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         4234
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.11513(7) 0.82188(9) 0.41036(8) 0.0363(3) Uani 1 1 d . . .
O1 O 0.07649(7) 0.72468(8) 0.50293(8) 0.0488(3) Uani 1 1 d . . .
H1 H 0.0791 0.7763 0.4734 0.073 Uiso 1 1 calc R . .
O2 O 0.08094(6) 0.55418(8) 0.59407(7) 0.0476(3) Uani 1 1 d . . .
C2 C 0.17814(8) 0.72444(12) 0.35658(9) 0.0386(3) Uani 1 1 d . . .
H2 H 0.2018 0.6580 0.3554 0.046 Uiso 1 1 calc R . .
C6 C 0.15139(8) 0.63115(11) 0.46059(9) 0.0356(3) Uani 1 1 d . . .
C4 C 0.13853(8) 0.91343(12) 0.31210(9) 0.0397(3) Uani 1 1 d . . .
H4 H 0.1340 0.9786 0.2793 0.048 Uiso 1 1 calc R . .
C7 C 0.11533(8) 0.63430(11) 0.50507(9) 0.0361(3) Uani 1 1 d . . .
C1 C 0.14835(8) 0.72768(11) 0.40765(9) 0.0351(3) Uani 1 1 d . . .
C8 C 0.11818(8) 0.54104(12) 0.55412(9) 0.0388(3) Uani 1 1 d . . .
C18 C 0.07599(8) 1.01473(12) 0.37487(9) 0.0361(3) Uani 1 1 d . . .
C3 C 0.17329(8) 0.81729(12) 0.30792(9) 0.0371(3) Uani 1 1 d . . .
C5 C 0.11054(8) 0.91346(11) 0.36439(9) 0.0359(3) Uani 1 1 d . . .
C9 C 0.15656(9) 0.44595(13) 0.55945(11) 0.0457(4) Uani 1 1 d . . .
H9 H 0.1583 0.3827 0.5924 0.055 Uiso 1 1 calc R . .
C13 C 0.27064(9) 0.75724(14) 0.28282(10) 0.0450(4) Uani 1 1 d . . .
H13 H 0.2945 0.7146 0.3367 0.054 Uiso 1 1 calc R . .
C11 C 0.19057(9) 0.53292(12) 0.46817(10) 0.0440(4) Uani 1 1 d . . .
H11 H 0.2159 0.5290 0.4394 0.053 Uiso 1 1 calc R . .
C10 C 0.19294(10) 0.44297(13) 0.51618(11) 0.0487(4) Uani 1 1 d . . .
H10 H 0.2197 0.3774 0.5202 0.058 Uiso 1 1 calc R . .
C23 C 0.02656(8) 1.00512(13) 0.40056(10) 0.0430(4) Uani 1 1 d . . .
H23 H 0.0132 0.9328 0.4091 0.052 Uiso 1 1 calc R . .
C12 C 0.20500(8) 0.81606(12) 0.25370(9) 0.0379(3) Uani 1 1 d . . .
C19 C 0.09359(9) 1.12190(12) 0.36220(11) 0.0474(4) Uani 1 1 d . . .
H19 H 0.1269 1.1308 0.3444 0.057 Uiso 1 1 calc R . .
C22 C -0.00325(9) 1.09916(13) 0.41376(11) 0.0480(4) Uani 1 1 d . . .
H22 H -0.0368 1.0908 0.4313 0.058 Uiso 1 1 calc R . .
C20 C 0.06349(10) 1.21543(13) 0.37506(12) 0.0534(4) Uani 1 1 d . . .
H20 H 0.0760 1.2879 0.3655 0.064 Uiso 1 1 calc R . .
C21 C 0.01529(10) 1.20517(13) 0.40176(11) 0.0493(4) Uani 1 1 d . . .
H21 H -0.0047 1.2699 0.4116 0.059 Uiso 1 1 calc R . .
C15 C 0.26756(10) 0.81915(14) 0.15571(11) 0.0515(4) Uani 1 1 d . . .
H15 H 0.2892 0.8207 0.1227 0.062 Uiso 1 1 calc R . .
C14 C 0.30183(10) 0.75988(15) 0.23427(11) 0.0516(4) Uani 1 1 d . . .
H14 H 0.3474 0.7202 0.2557 0.062 Uiso 1 1 calc R . .
C17 C 0.17081(10) 0.87538(15) 0.17389(11) 0.0521(4) Uani 1 1 d . . .
H17 H 0.1255 0.9159 0.1524 0.063 Uiso 1 1 calc R . .
C26 C 0.04562(11) 0.49977(17) 0.69061(13) 0.0606(5) Uani 1 1 d . . .
H26A H 0.0706 0.5659 0.7286 0.091 Uiso 1 1 calc R . .
H26B H 0.0470 0.4383 0.7273 0.091 Uiso 1 1 calc R . .
H26C H -0.0071 0.5180 0.6429 0.091 Uiso 1 1 calc R . .
C25 C 0.08605(11) 0.46470(15) 0.64931(12) 0.0552(4) Uani 1 1 d . . .
H25A H 0.1398 0.4482 0.6970 0.066 Uiso 1 1 calc R . .
H25B H 0.0624 0.3962 0.6127 0.066 Uiso 1 1 calc R . .
C16 C 0.20173(10) 0.87647(16) 0.12480(12) 0.0570(5) Uani 1 1 d . . .
H16 H 0.1773 0.9169 0.0698 0.068 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 C5 1.3436(17) . ?
N1 C1 1.3487(17) . ?
O1 C7 1.3522(16) . ?
O2 C8 1.3674(16) . ?
O2 C25 1.4251(18) . ?
C2 C3 1.383(2) . ?
C2 C1 1.4016(18) . ?
C6 C11 1.4044(19) . ?
C6 C7 1.4092(18) . ?
C6 C1 1.4772(19) . ?
C4 C5 1.3890(18) . ?
C4 C3 1.396(2) . ?
C7 C8 1.4043(19) . ?
C8 C9 1.375(2) . ?
C18 C19 1.390(2) . ?
C18 C23 1.3943(19) . ?
C18 C5 1.4881(18) . ?
C3 C12 1.4887(17) . ?
C9 C10 1.396(2) . ?
C13 C14 1.385(2) . ?
C13 C12 1.385(2) . ?
C11 C10 1.365(2) . ?
C23 C22 1.381(2) . ?
C12 C17 1.385(2) . ?
C19 C20 1.377(2) . ?
C22 C21 1.381(2) . ?
C20 C21 1.384(2) . ?
C15 C14 1.368(2) . ?
C15 C16 1.373(2) . ?
C17 C16 1.388(2) . ?
C26 C25 1.501(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
C5 N1 C1 120.31(11) . . ?
C8 O2 C25 117.22(11) . . ?
C3 C2 C1 120.45(13) . . ?
C11 C6 C7 117.80(12) . . ?
C11 C6 C1 120.82(12) . . ?
C7 C6 C1 121.38(12) . . ?
C5 C4 C3 119.78(13) . . ?
O1 C7 C8 116.70(11) . . ?
O1 C7 C6 122.88(12) . . ?
C8 C7 C6 120.42(12) . . ?
N1 C1 C2 120.24(12) . . ?
N1 C1 C6 116.77(11) . . ?
C2 C1 C6 122.99(12) . . ?
O2 C8 C9 124.89(13) . . ?
O2 C8 C7 114.96(12) . . ?
C9 C8 C7 120.16(13) . . ?
C19 C18 C23 117.78(13) . . ?
C19 C18 C5 121.32(12) . . ?
C23 C18 C5 120.87(12) . . ?
C2 C3 C4 117.90(12) . . ?
C2 C3 C12 121.40(12) . . ?
C4 C3 C12 120.70(13) . . ?
N1 C5 C4 121.32(12) . . ?
N1 C5 C18 116.29(11) . . ?
C4 C5 C18 122.37(12) . . ?
C8 C9 C10 119.56(14) . . ?
C14 C13 C12 120.73(15) . . ?
C10 C11 C6 121.13(13) . . ?
C11 C10 C9 120.92(14) . . ?
C22 C23 C18 120.97(14) . . ?
C17 C12 C13 118.09(13) . . ?
C17 C12 C3 121.15(13) . . ?
C13 C12 C3 120.75(13) . . ?
C20 C19 C18 121.06(14) . . ?
C21 C22 C23 120.63(14) . . ?
C19 C20 C21 120.78(14) . . ?
C22 C21 C20 118.77(14) . . ?
C14 C15 C16 119.72(14) . . ?
C15 C14 C13 120.50(15) . . ?
C12 C17 C16 120.94(15) . . ?
O2 C25 C26 108.18(13) . . ?
C15 C16 C17 120.00(16) . . ?

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
C11 C6 C7 O1 179.52(13) . . . . ?
C1 C6 C7 O1 -0.4(2) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C1 C6 C7 C8 179.22(13) . . . . ?
C5 N1 C1 C2 -0.2(2) . . . . ?
C5 N1 C1 C6 179.63(12) . . . . ?
C3 C2 C1 N1 -0.5(2) . . . . ?
C3 C2 C1 C6 179.65(13) . . . . ?
C11 C6 C1 N1 -174.44(13) . . . . ?
C7 C6 C1 N1 5.5(2) . . . . ?
C11 C6 C1 C2 5.4(2) . . . . ?
C7 C6 C1 C2 -174.63(14) . . . . ?
C25 O2 C8 C9 3.6(2) . . . . ?
C25 O2 C8 C7 -176.17(14) . . . . ?
O1 C7 C8 O2 -0.2(2) . . . . ?
C6 C7 C8 O2 -179.87(13) . . . . ?
O1 C7 C8 C9 179.99(14) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C1 C2 C3 C12 179.57(13) . . . . ?
C5 C4 C3 C2 0.3(2) . . . . ?
C5 C4 C3 C12 -178.83(13) . . . . ?
C1 N1 C5 C4 1.0(2) . . . . ?
C1 N1 C5 C18 -177.37(12) . . . . ?
C3 C4 C5 N1 -1.0(2) . . . . ?
C3 C4 C5 C18 177.23(13) . . . . ?
C19 C18 C5 N1 154.41(14) . . . . ?
C23 C18 C5 N1 -23.55(19) . . . . ?
C19 C18 C5 C4 -23.9(2) . . . . ?
C23 C18 C5 C4 158.10(14) . . . . ?
O2 C8 C9 C10 -179.51(14) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C7 C6 C11 C10 0.7(2) . . . . ?
C1 C6 C11 C10 -179.30(15) . . . . ?
C6 C11 C10 C9 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
C5 C18 C23 C22 177.43(14) . . . . ?
C14 C13 C12 C17 1.3(2) . . . . ?
C14 C13 C12 C3 -177.32(14) . . . . ?
C2 C3 C12 C17 146.34(15) . . . . ?
C4 C3 C12 C17 -34.6(2) . . . . ?
C2 C3 C12 C13 -35.1(2) . . . . ?
C4 C3 C12 C13 144.04(15) . . . . ?
C23 C18 C19 C20 0.3(2) . . . . ?
C5 C18 C19 C20 -177.70(15) . . . . ?
C18 C23 C22 C21 0.0(2) . . . . ?
C18 C19 C20 C21 0.6(3) . . . . ?
C23 C22 C21 C20 0.9(3) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C16 C15 C14 C13 0.0(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C13 C12 C17 C16 -0.4(2) . . . . ?
C3 C12 C17 C16 178.22(16) . . . . ?
C8 O2 C25 C26 176.43(14) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C12 C17 C16 C15 -0.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.80 2.5465(14) 147.3 .

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_001
_database_code_depnum_ccdc_archive 'CCDC 1502300'
_audit_update_record             
;
2016-09-02 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H17 N O'
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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                   8.7224(7)
_cell_length_b                   20.6209(19)
_cell_length_c                   9.7045(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.261(3)
_cell_angle_gamma                90.00
_cell_volume                     1657.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296
_cell_measurement_reflns_used    6455
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.37

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17754
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0423
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         27.52
_reflns_number_total             3818
_reflns_number_gt                2552
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.1249P)²+0.5036P] 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         3765
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0649
_refine_ls_wR_factor_ref         0.2235
_refine_ls_wR_factor_gt          0.1946
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.4703(2) 0.70303(8) 0.98149(19) 0.0402(5) Uani 1 1 d . . .
C2 C 0.4792(2) 0.81825(10) 0.9889(2) 0.0410(5) Uani 1 1 d . . .
H2 H 0.4398 0.8579 1.0147 0.049 Uiso 1 1 calc R . .
C4 C 0.6571(3) 0.75973(10) 0.8930(2) 0.0405(5) Uani 1 1 d . . .
H4 H 0.7406 0.7585 0.8494 0.049 Uiso 1 1 calc R . .
C5 C 0.5909(2) 0.70264(10) 0.9220(2) 0.0379(5) Uani 1 1 d . . .
C1 C 0.4129(2) 0.75976(10) 1.0133(2) 0.0380(5) Uani 1 1 d . . .
C3 C 0.6025(2) 0.81899(10) 0.9270(2) 0.0375(5) Uani 1 1 d . . .
C6 C 0.2811(3) 0.75642(10) 1.0787(2) 0.0402(5) Uani 1 1 d . . .
O1 O 0.3010(3) 0.64022(9) 1.1086(3) 0.0803(7) Uani 1 1 d . . .
H1 H 0.3661 0.6459 1.0617 0.120 Uiso 1 1 calc R . .
C18 C 0.6517(2) 0.63807(10) 0.8955(2) 0.0394(5) Uani 1 1 d . . .
C7 C 0.2342(3) 0.69749(11) 1.1253(3) 0.0457(6) Uani 1 1 d . . .
C12 C 0.6755(2) 0.88105(10) 0.9006(2) 0.0381(5) Uani 1 1 d . . .
C19 C 0.8112(3) 0.63008(11) 0.8978(2) 0.0446(5) Uani 1 1 d . . .
H19 H 0.8804 0.6667 0.9118 0.054 Uiso 1 1 calc R . .
C17 C 0.7395(3) 0.88727(11) 0.7868(3) 0.0456(6) Uani 1 1 d . . .
H17 H 0.7350 0.8516 0.7237 0.055 Uiso 1 1 calc R . .
C9 C 0.0356(3) 0.75134(13) 1.2059(3) 0.0656(8) Uani 1 1 d . . .
H9 H -0.0468 0.7496 1.2508 0.079 Uiso 1 1 calc R . .
C23 C 0.5527(3) 0.58330(11) 0.8735(3) 0.0489(6) Uani 1 1 d . . .
H23 H 0.4436 0.5875 0.8716 0.059 Uiso 1 1 calc R . .
C20 C 0.8696(3) 0.56937(11) 0.8798(3) 0.0517(6) Uani 1 1 d . . .
H20 H 0.9786 0.5646 0.8818 0.062 Uiso 1 1 calc R . .
C8 C 0.1132(3) 0.69643(13) 1.1905(3) 0.0577(7) Uani 1 1 d . . .
H8 H 0.0846 0.6565 1.2247 0.069 Uiso 1 1 calc R . .
C10 C 0.0752(3) 0.80999(14) 1.1570(4) 0.0693(8) Uani 1 1 d . . .
H10 H 0.0192 0.8485 1.1660 0.083 Uiso 1 1 calc R . .
C22 C 0.6124(3) 0.52286(11) 0.8544(3) 0.0557(6) Uani 1 1 d . . .
H22 H 0.5436 0.4860 0.8380 0.067 Uiso 1 1 calc R . .
C13 C 0.6830(3) 0.93419(11) 0.9898(3) 0.0501(6) Uani 1 1 d . . .
H13 H 0.6381 0.9314 1.0671 0.060 Uiso 1 1 calc R . .
C14 C 0.7546(3) 0.99094(11) 0.9675(3) 0.0594(7) Uani 1 1 d . . .
H14 H 0.7604 1.0267 1.0306 0.071 Uiso 1 1 calc R . .
C21 C 0.7709(3) 0.51589(12) 0.8590(3) 0.0550(6) Uani 1 1 d . . .
H21 H 0.8120 0.4742 0.8479 0.066 Uiso 1 1 calc R . .
C11 C 0.1972(3) 0.81171(12) 1.0951(3) 0.0592(7) Uani 1 1 d . . .
H11 H 0.2251 0.8521 1.0624 0.071 Uiso 1 1 calc R . .
C15 C 0.8181(3) 0.99650(12) 0.8548(3) 0.0590(7) Uani 1 1 d . . .
H15 H 0.8674 1.0358 0.8400 0.071 Uiso 1 1 calc R . .
C16 C 0.8094(3) 0.94481(12) 0.7645(3) 0.0538(6) Uani 1 1 d . . .
H16 H 0.8518 0.9485 0.6858 0.065 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 1.346(3) . ?
N1 C5 1.349(2) . ?
C2 C3 1.387(3) . ?
C2 C1 1.389(3) . ?
C4 C5 1.379(3) . ?
C4 C3 1.388(3) . ?
C5 C18 1.485(3) . ?
C1 C6 1.478(3) . ?
C3 C12 1.487(3) . ?
C6 C11 1.391(3) . ?
C6 C7 1.402(3) . ?
O1 C7 1.349(3) . ?
C18 C19 1.394(3) . ?
C18 C23 1.397(3) . ?
C7 C8 1.390(3) . ?
C12 C13 1.386(3) . ?
C12 C17 1.390(3) . ?
C19 C20 1.383(3) . ?
C17 C16 1.382(3) . ?
C9 C8 1.352(4) . ?
C9 C10 1.382(4) . ?
C23 C22 1.385(3) . ?
C20 C21 1.374(3) . ?
C10 C11 1.377(3) . ?
C22 C21 1.376(4) . ?
C13 C14 1.376(3) . ?
C14 C15 1.377(4) . ?
C15 C16 1.367(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 119.94(17) . . ?
C3 C2 C1 120.25(18) . . ?
C5 C4 C3 120.39(18) . . ?
N1 C5 C4 121.02(18) . . ?
N1 C5 C18 116.63(17) . . ?
C4 C5 C18 122.31(17) . . ?
N1 C1 C2 120.74(18) . . ?
N1 C1 C6 116.94(17) . . ?
C2 C1 C6 122.30(18) . . ?
C2 C3 C4 117.63(18) . . ?
C2 C3 C12 121.09(18) . . ?
C4 C3 C12 121.26(17) . . ?
C11 C6 C7 117.15(19) . . ?
C11 C6 C1 121.25(19) . . ?
C7 C6 C1 121.60(18) . . ?
C19 C18 C23 118.21(19) . . ?
C19 C18 C5 120.80(18) . . ?
C23 C18 C5 120.93(18) . . ?
O1 C7 C8 117.3(2) . . ?
O1 C7 C6 122.63(18) . . ?
C8 C7 C6 120.0(2) . . ?
C13 C12 C17 118.15(19) . . ?
C13 C12 C3 120.74(18) . . ?
C17 C12 C3 121.11(18) . . ?
C20 C19 C18 120.7(2) . . ?
C16 C17 C12 120.7(2) . . ?
C8 C9 C10 120.5(2) . . ?
C22 C23 C18 120.5(2) . . ?
C21 C20 C19 120.4(2) . . ?
C9 C8 C7 121.0(2) . . ?
C11 C10 C9 118.9(2) . . ?
C21 C22 C23 120.4(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 120.8(2) . . ?
C20 C21 C22 119.8(2) . . ?
C10 C11 C6 122.4(2) . . ?
C16 C15 C14 119.3(2) . . ?
C15 C16 C17 120.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 0.0(3) . . . . ?
C1 N1 C5 C18 177.67(18) . . . . ?
C3 C4 C5 N1 1.2(3) . . . . ?
C3 C4 C5 C18 -176.36(19) . . . . ?
C5 N1 C1 C2 -1.6(3) . . . . ?
C5 N1 C1 C6 -179.84(18) . . . . ?
C3 C2 C1 N1 2.0(3) . . . . ?
C3 C2 C1 C6 -179.86(19) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C12 -179.72(19) . . . . ?
C5 C4 C3 C2 -0.7(3) . . . . ?
C5 C4 C3 C12 178.2(2) . . . . ?
N1 C1 C6 C11 -170.1(2) . . . . ?
C2 C1 C6 C11 11.7(4) . . . . ?
N1 C1 C6 C7 9.2(3) . . . . ?
C2 C1 C6 C7 -169.0(2) . . . . ?
N1 C5 C18 C19 -151.1(2) . . . . ?
C4 C5 C18 C19 26.5(3) . . . . ?
N1 C5 C18 C23 26.3(3) . . . . ?
C4 C5 C18 C23 -156.1(2) . . . . ?
C11 C6 C7 O1 176.7(2) . . . . ?
C1 C6 C7 O1 -2.7(4) . . . . ?
C11 C6 C7 C8 -2.7(4) . . . . ?
C1 C6 C7 C8 178.0(2) . . . . ?
C2 C3 C12 C13 30.3(3) . . . . ?
C4 C3 C12 C13 -148.6(2) . . . . ?
C2 C3 C12 C17 -150.3(2) . . . . ?
C4 C3 C12 C17 30.8(3) . . . . ?
C23 C18 C19 C20 -0.5(3) . . . . ?
C5 C18 C19 C20 176.9(2) . . . . ?
C13 C12 C17 C16 0.5(3) . . . . ?
C3 C12 C17 C16 -178.9(2) . . . . ?
C19 C18 C23 C22 -0.1(3) . . . . ?
C5 C18 C23 C22 -177.5(2) . . . . ?
C18 C19 C20 C21 0.2(4) . . . . ?
C10 C9 C8 C7 0.0(4) . . . . ?
O1 C7 C8 C9 -177.3(3) . . . . ?
C6 C7 C8 C9 2.1(4) . . . . ?
C8 C9 C10 C11 -1.3(5) . . . . ?
C18 C23 C22 C21 1.0(4) . . . . ?
C17 C12 C13 C14 -1.3(4) . . . . ?
C3 C12 C13 C14 178.2(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C19 C20 C21 C22 0.8(4) . . . . ?
C23 C22 C21 C20 -1.3(4) . . . . ?
C9 C10 C11 C6 0.6(5) . . . . ?
C7 C6 C11 C10 1.4(4) . . . . ?
C1 C6 C11 C10 -179.3(3) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C12 C17 C16 C15 0.5(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 1.81 2.554(2) 147.3 .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.52
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.708
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.083
