# 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_ap_kd_421a
_audit_block_doi                 10.5517/cc1jylsv
_database_code_depnum_ccdc_archive 'CCDC 1428628'
_audit_update_record             
;
2015-09-30 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 N2 O2'
_chemical_formula_weight         385.47

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.5334(5)
_cell_length_b                   10.8799(7)
_cell_length_c                   12.6877(8)
_cell_angle_alpha                69.923(2)
_cell_angle_beta                 79.961(2)
_cell_angle_gamma                84.106(2)
_cell_volume                     1088.27(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             410
_exptl_absorpt_coefficient_mu    0.075
_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(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13448
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.73
_diffrn_reflns_theta_max         26.43
_reflns_number_total             4314
_reflns_number_gt                2595
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.2000P)²+0.0000P] 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         4314
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0986
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.2438
_refine_ls_wR_factor_gt          0.1887
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_restrained_S_all      0.836
_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
O1 O 0.6200(2) 0.43349(17) 1.12673(15) 0.0718(6) Uani 1 1 d . . .
O2 O 0.8789(2) -0.08038(16) 1.10191(19) 0.0873(7) Uani 1 1 d . . .
N1 N 0.8037(2) 0.13348(18) 1.08578(17) 0.0579(6) Uani 1 1 d . . .
N2 N 0.9613(2) 0.32536(17) 0.83428(16) 0.0555(5) Uani 1 1 d . . .
H2 H 0.9564 0.2447 0.8772 0.067 Uiso 1 1 calc R . .
C2 C 0.7544(4) 0.1010(4) 1.2916(3) 0.0924(10) Uani 1 1 d . . .
H2A H 0.7238 0.0117 1.3105 0.111 Uiso 1 1 calc R . .
H2B H 0.6588 0.1579 1.2821 0.111 Uiso 1 1 calc R . .
C3 C 0.8678(4) 0.1377(3) 1.1822(2) 0.0722(8) Uani 1 1 d . . .
H3 H 0.9713 0.1613 1.1771 0.087 Uiso 1 1 calc R . .
C4 C 0.6997(3) 0.2401(2) 1.02299(19) 0.0491(6) Uani 1 1 d . . .
H4 H 0.6026 0.2455 1.0756 0.059 Uiso 1 1 calc R . .
C5 C 0.7669(2) 0.37548(19) 0.97439(19) 0.0469(5) Uani 1 1 d . . .
C6 C 0.8780(2) 0.41366(19) 0.87858(19) 0.0465(5) Uani 1 1 d . . .
C7 C 1.0560(3) 0.3492(2) 0.7256(2) 0.0533(6) Uani 1 1 d . . .
C8 C 1.1914(3) 0.4196(3) 0.6933(2) 0.0778(8) Uani 1 1 d . . .
H8 H 1.2225 0.4572 0.7416 0.093 Uiso 1 1 calc R . .
C9 C 1.2805(4) 0.4338(4) 0.5885(3) 0.0961(11) Uani 1 1 d . . .
H9 H 1.3713 0.4823 0.5672 0.115 Uiso 1 1 calc R . .
C10 C 1.2411(4) 0.3794(4) 0.5143(3) 0.0864(10) Uani 1 1 d . . .
C11 C 1.3433(5) 0.3919(6) 0.4011(3) 0.144(2) Uani 1 1 d . . .
H11A H 1.3060 0.3355 0.3678 0.216 Uiso 1 1 calc R . .
H11B H 1.4520 0.3671 0.4124 0.216 Uiso 1 1 calc R . .
H11C H 1.3367 0.4809 0.3514 0.216 Uiso 1 1 calc R . .
C12 C 1.0143(4) 0.2948(3) 0.6528(3) 0.0814(9) Uani 1 1 d . . .
H12 H 0.9224 0.2477 0.6732 0.098 Uiso 1 1 calc R . .
C13 C 1.1070(4) 0.3090(4) 0.5493(3) 0.0989(11) Uani 1 1 d . . .
H13 H 1.0773 0.2695 0.5018 0.119 Uiso 1 1 calc R . .
C14 C 0.7051(3) 0.4671(2) 1.0338(2) 0.0527(6) Uani 1 1 d . . .
C15 C 0.7493(3) 0.6083(2) 0.9780(2) 0.0600(7) Uani 1 1 d . . .
H15A H 0.6630 0.6648 0.9989 0.072 Uiso 1 1 calc R . .
H15B H 0.8433 0.6218 1.0054 0.072 Uiso 1 1 calc R . .
C16 C 0.7820(3) 0.6452(2) 0.8505(2) 0.0555(6) Uani 1 1 d . . .
H16A H 0.8137 0.7352 0.8171 0.067 Uiso 1 1 calc R . .
H16B H 0.6861 0.6382 0.8221 0.067 Uiso 1 1 calc R . .
C17 C 0.9131(3) 0.5553(2) 0.8173(2) 0.0543(6) Uani 1 1 d . . .
H17A H 0.9250 0.5727 0.7361 0.065 Uiso 1 1 calc R . .
H17B H 1.0129 0.5730 0.8348 0.065 Uiso 1 1 calc R . .
C18 C 0.6557(3) 0.1849(2) 0.9383(2) 0.0507(6) Uani 1 1 d . . .
C19 C 0.5670(3) 0.2415(3) 0.8513(2) 0.0620(7) Uani 1 1 d . . .
H19 H 0.5256 0.3272 0.8358 0.074 Uiso 1 1 calc R . .
C20 C 0.5415(4) 0.1654(3) 0.7872(3) 0.0793(9) Uani 1 1 d . . .
H20 H 0.4822 0.2011 0.7279 0.095 Uiso 1 1 calc R . .
C21 C 0.6030(4) 0.0380(3) 0.8108(3) 0.0886(10) Uani 1 1 d . . .
H21 H 0.5843 -0.0109 0.7673 0.106 Uiso 1 1 calc R . .
C22 C 0.6918(4) -0.0179(3) 0.8978(3) 0.0764(9) Uani 1 1 d . . .
H22 H 0.7326 -0.1038 0.9136 0.092 Uiso 1 1 calc R . .
C23 C 0.7186(3) 0.0574(2) 0.9611(2) 0.0583(7) Uani 1 1 d . . .
C24 C 0.8089(3) 0.0237(2) 1.0560(2) 0.0623(7) Uani 1 1 d . . .
H70 H 0.953(4) 0.071(3) 1.192(2) 0.090(10) Uiso 1 1 d . . .
C70 C 0.8279(6) 0.1125(6) 1.3886(3) 0.1416(18) Uani 1 1 d . . .
H70A H 0.8603 0.2016 1.3680 0.170 Uiso 1 1 calc R . .
H70B H 0.9232 0.0553 1.3973 0.170 Uiso 1 1 calc R . .
C71 C 0.7242(8) 0.0799(8) 1.4975(4) 0.216(4) Uani 1 1 d . . .
H71A H 0.6401 0.1462 1.4945 0.324 Uiso 1 1 calc R . .
H71B H 0.7849 0.0753 1.5559 0.324 Uiso 1 1 calc R . .
H71C H 0.6794 -0.0033 1.5141 0.324 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 C14 1.229(3) . ?
O2 C24 1.228(3) . ?
N1 C24 1.365(3) . ?
N1 C3 1.441(4) . ?
N1 C4 1.472(3) . ?
N2 C6 1.355(3) . ?
N2 C7 1.425(3) . ?
N2 H2 0.8600 . ?
C2 C3 1.502(4) . ?
C2 C70 1.520(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3 0.9300 . ?
C3 H70 0.97(3) . ?
C4 C18 1.512(3) . ?
C4 C5 1.518(3) . ?
C4 H4 0.9800 . ?
C5 C6 1.372(3) . ?
C5 C14 1.452(3) . ?
C6 C17 1.503(3) . ?
C7 C12 1.365(4) . ?
C7 C8 1.374(4) . ?
C8 C9 1.378(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(5) . ?
C9 H9 0.9300 . ?
C10 C13 1.364(4) . ?
C10 C11 1.515(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.378(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.512(3) . ?
C15 C16 1.509(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.510(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C23 1.387(3) . ?
C18 C19 1.378(4) . ?
C19 C20 1.398(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.377(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.463(4) . ?
C70 C71 1.457(6) . ?
C70 H70A 0.9700 . ?
C70 H70B 0.9700 . ?
C71 H71A 0.9600 . ?
C71 H71B 0.9600 . ?
C71 H71C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 N1 C3 123.8(2) . . ?
C24 N1 C4 112.9(2) . . ?
C3 N1 C4 122.4(2) . . ?
C6 N2 C7 128.20(18) . . ?
C6 N2 H2 115.9 . . ?
C7 N2 H2 115.9 . . ?
C3 C2 C70 111.8(3) . . ?
C3 C2 H2A 109.3 . . ?
C70 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C70 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
N1 C3 C2 114.7(2) . . ?
N1 C3 H3 122.7 . . ?
C2 C3 H3 122.7 . . ?
N1 C3 H70 104.5(18) . . ?
C2 C3 H70 106.0(18) . . ?
H3 C3 H70 60.7 . . ?
N1 C4 C18 101.86(16) . . ?
N1 C4 C5 116.37(18) . . ?
C18 C4 C5 116.16(18) . . ?
N1 C4 H4 107.3 . . ?
C18 C4 H4 107.3 . . ?
C5 C4 H4 107.3 . . ?
C6 C5 C14 120.14(19) . . ?
C6 C5 C4 123.41(18) . . ?
C14 C5 C4 116.44(18) . . ?
N2 C6 C5 121.54(18) . . ?
N2 C6 C17 116.68(19) . . ?
C5 C6 C17 121.78(18) . . ?
C12 C7 C8 118.8(2) . . ?
C12 C7 N2 118.5(2) . . ?
C8 C7 N2 122.7(2) . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 122.8(3) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C9 C10 C13 116.5(3) . . ?
C9 C10 C11 122.2(3) . . ?
C13 C10 C11 121.2(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C7 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
C12 C13 C10 121.9(3) . . ?
C12 C13 H13 119.0 . . ?
C10 C13 H13 119.0 . . ?
O1 C14 C5 122.5(2) . . ?
O1 C14 C15 119.7(2) . . ?
C5 C14 C15 117.8(2) . . ?
C16 C15 C14 111.46(19) . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 109.7(2) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C6 C17 C16 111.55(19) . . ?
C6 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C6 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C23 C18 C19 121.3(2) . . ?
C23 C18 C4 108.7(2) . . ?
C19 C18 C4 130.0(2) . . ?
C20 C19 C18 117.7(3) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C22 C21 C20 121.1(3) . . ?
C22 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C21 C22 C23 118.3(3) . . ?
C21 C22 H22 120.9 . . ?
C23 C22 H22 120.9 . . ?
C18 C23 C22 120.7(3) . . ?
C18 C23 C24 109.7(2) . . ?
C22 C23 C24 129.6(2) . . ?
O2 C24 N1 124.7(3) . . ?
O2 C24 C23 128.8(3) . . ?
N1 C24 C23 106.5(2) . . ?
C2 C70 C71 115.1(4) . . ?
C2 C70 H70A 108.5 . . ?
C71 C70 H70A 108.5 . . ?
C2 C70 H70B 108.5 . . ?
C71 C70 H70B 108.5 . . ?
H70A C70 H70B 107.5 . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        26.43
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_aa
_audit_block_doi                 10.5517/cc1k4yk6
_database_code_depnum_ccdc_archive 'CCDC 1434728'
_audit_update_record             
;
2015-11-02 deposited with the CCDC.
2016-02-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 F N4 O4'
_chemical_formula_weight         410.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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                   11.293(2)
_cell_length_b                   12.118(2)
_cell_length_c                   14.030(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.621(8)
_cell_angle_gamma                90.00
_cell_volume                     1903.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.101
_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(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29305
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0313
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         33.63
_reflns_number_total             7374
_reflns_number_gt                5040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0060P)²+2.0000P] 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         7374
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0960
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.1490
_refine_ls_wR_factor_gt          0.1378
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.004
_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
F1 F 0.60890(15) 0.13727(16) -0.02712(15) 0.1000(6) Uani 1 1 d . . .
O1 O 0.45729(15) 0.07643(13) 0.20995(12) 0.0647(4) Uani 1 1 d . . .
O2 O 0.08404(12) 0.17981(11) 0.08897(12) 0.0542(4) Uani 1 1 d . . .
O3 O 0.19640(16) 0.60428(14) -0.09235(12) 0.0689(5) Uani 1 1 d . . .
N1 N 0.16545(13) 0.44357(13) -0.01185(11) 0.0417(3) Uani 1 1 d . . .
C22 C 0.13827(14) 0.40666(14) 0.08311(13) 0.0365(3) Uani 1 1 d . . .
H22 H 0.0581 0.3741 0.0745 0.044 Uiso 1 1 calc R . .
C23 C 0.22460(14) 0.32110(13) 0.12862(12) 0.0333(3) Uani 1 1 d . . .
N4 N 0.26768(14) 0.13003(12) 0.16150(12) 0.0423(3) Uani 1 1 d . . .
C1 C 0.5038(2) 0.1928(2) -0.04643(18) 0.0634(6) Uani 1 1 d . . .
C2 C 0.5066(2) 0.3052(2) -0.04496(17) 0.0592(5) Uani 1 1 d . . .
H2 H 0.5787 0.3431 -0.0329 0.071 Uiso 1 1 calc R . .
C3 C 0.39961(19) 0.36143(17) -0.06189(15) 0.0504(5) Uani 1 1 d . . .
H3 H 0.3996 0.4382 -0.0619 0.060 Uiso 1 1 calc R . .
C4 C 0.29226(18) 0.30490(16) -0.07881(13) 0.0446(4) Uani 1 1 d . . .
C5 C 0.17553(19) 0.36682(19) -0.09004(15) 0.0527(5) Uani 1 1 d . . .
H5A H 0.1673 0.4073 -0.1502 0.063 Uiso 1 1 calc R . .
H5B H 0.1104 0.3141 -0.0935 0.063 Uiso 1 1 calc R . .
C6 C 0.18468(15) 0.20967(14) 0.12361(13) 0.0375(3) Uani 1 1 d . . .
C7 C 0.38595(17) 0.15081(16) 0.18814(13) 0.0435(4) Uani 1 1 d . . .
C8 C 0.4013(2) 0.13331(19) -0.06641(18) 0.0652(6) Uani 1 1 d . . .
H8 H 0.4029 0.0567 -0.0693 0.078 Uiso 1 1 calc R . .
C9 C 0.2948(2) 0.19066(18) -0.08220(16) 0.0555(5) Uani 1 1 d . . .
H9 H 0.2234 0.1519 -0.0954 0.067 Uiso 1 1 calc R . .
C10 C 0.2293(2) 0.01454(16) 0.1634(2) 0.0642(6) Uani 1 1 d . . .
H10A H 0.2476 -0.0224 0.1066 0.096 Uiso 1 1 calc R . .
H10B H 0.1448 0.0116 0.1656 0.096 Uiso 1 1 calc R . .
H10C H 0.2705 -0.0212 0.2192 0.096 Uiso 1 1 calc R . .
N70 N 0.42102(13) 0.25964(13) 0.18886(11) 0.0402(3) Uani 1 1 d . . .
C12 C 0.54937(17) 0.2824(2) 0.21217(17) 0.0574(5) Uani 1 1 d . . .
H12A H 0.5923 0.2140 0.2206 0.086 Uiso 1 1 calc R . .
H12B H 0.5632 0.3247 0.2704 0.086 Uiso 1 1 calc R . .
H12C H 0.5765 0.3233 0.1606 0.086 Uiso 1 1 calc R . .
C13 C 0.34168(14) 0.34367(14) 0.16200(12) 0.0348(3) Uani 1 1 d . . .
N10 N 0.38704(14) 0.44639(13) 0.16551(12) 0.0470(4) Uani 1 1 d . . .
H10D H 0.4619 0.4567 0.1838 0.056 Uiso 1 1 calc R . .
H10E H 0.3411 0.5018 0.1494 0.056 Uiso 1 1 calc R . .
C15 C 0.13219(15) 0.51573(14) 0.13449(14) 0.0398(4) Uani 1 1 d . . .
C16 C 0.11345(19) 0.53703(18) 0.22805(16) 0.0521(5) Uani 1 1 d . . .
H16 H 0.0997 0.4800 0.2696 0.063 Uiso 1 1 calc R . .
C17 C 0.1158(2) 0.6468(2) 0.25826(18) 0.0619(6) Uani 1 1 d . . .
H17 H 0.1043 0.6631 0.3212 0.074 Uiso 1 1 calc R . .
C18 C 0.1348(2) 0.73150(19) 0.1964(2) 0.0642(6) Uani 1 1 d . . .
H18 H 0.1353 0.8040 0.2183 0.077 Uiso 1 1 calc R . .
C19 C 0.15289(19) 0.71088(17) 0.10303(19) 0.0568(5) Uani 1 1 d . . .
H19 H 0.1652 0.7682 0.0614 0.068 Uiso 1 1 calc R . .
C20 C 0.15213(15) 0.60133(15) 0.07298(15) 0.0426(4) Uani 1 1 d . . .
C21 C 0.17388(16) 0.55497(16) -0.02079(15) 0.0460(4) Uani 1 1 d . . .
O10 O 0.0557(6) 0.0185(6) 0.9458(4) 0.300(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.360(3) . ?
O1 C7 1.221(2) . ?
O2 C6 1.230(2) . ?
O3 C21 1.224(2) . ?
N1 C21 1.360(2) . ?
N1 C5 1.454(2) . ?
N1 C22 1.476(2) . ?
C22 C23 1.506(2) . ?
C22 C15 1.511(2) . ?
C22 H22 0.9800 . ?
C23 C13 1.370(2) . ?
C23 C6 1.422(2) . ?
N4 C7 1.362(2) . ?
N4 C6 1.400(2) . ?
N4 C10 1.466(2) . ?
C1 C8 1.360(4) . ?
C1 C2 1.363(3) . ?
C2 C3 1.380(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C9 1.386(3) . ?
C4 C5 1.507(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 N70 1.377(2) . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N70 C13 1.376(2) . ?
N70 C12 1.469(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N10 1.344(2) . ?
N10 H10D 0.8600 . ?
N10 H10E 0.8600 . ?
C15 C16 1.381(3) . ?
C15 C20 1.387(3) . ?
C16 C17 1.396(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.393(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.481(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
C21 N1 C5 123.49(18) . . ?
C21 N1 C22 114.17(15) . . ?
C5 N1 C22 122.25(16) . . ?
N1 C22 C23 113.02(14) . . ?
N1 C22 C15 101.16(14) . . ?
C23 C22 C15 117.88(14) . . ?
N1 C22 H22 108.1 . . ?
C23 C22 H22 108.1 . . ?
C15 C22 H22 108.1 . . ?
C13 C23 C6 119.43(15) . . ?
C13 C23 C22 123.26(14) . . ?
C6 C23 C22 116.72(14) . . ?
C7 N4 C6 124.03(15) . . ?
C7 N4 C10 116.92(17) . . ?
C6 N4 C10 118.71(17) . . ?
C8 C1 F1 118.4(2) . . ?
C8 C1 C2 123.4(2) . . ?
F1 C1 C2 118.3(2) . . ?
C1 C2 C3 118.2(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C9 118.6(2) . . ?
C3 C4 C5 120.35(19) . . ?
C9 C4 C5 121.0(2) . . ?
N1 C5 C4 113.24(15) . . ?
N1 C5 H5A 108.9 . . ?
C4 C5 H5A 108.9 . . ?
N1 C5 H5B 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O2 C6 N4 118.97(16) . . ?
O2 C6 C23 124.68(16) . . ?
N4 C6 C23 116.35(15) . . ?
O1 C7 N4 121.54(19) . . ?
O1 C7 N70 121.73(19) . . ?
N4 C7 N70 116.73(15) . . ?
C1 C8 C9 117.7(2) . . ?
C1 C8 H8 121.1 . . ?
C9 C8 H8 121.1 . . ?
C8 C9 C4 121.2(2) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 N70 C7 122.06(15) . . ?
C13 N70 C12 120.65(16) . . ?
C7 N70 C12 117.10(16) . . ?
N70 C12 H12A 109.5 . . ?
N70 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N70 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N10 C13 N70 116.37(15) . . ?
N10 C13 C23 122.88(15) . . ?
N70 C13 C23 120.65(15) . . ?
C13 N10 H10D 120.0 . . ?
C13 N10 H10E 120.0 . . ?
H10D N10 H10E 120.0 . . ?
C16 C15 C20 120.64(18) . . ?
C16 C15 C22 129.71(18) . . ?
C20 C15 C22 109.63(16) . . ?
C15 C16 C17 117.9(2) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C18 C17 C16 121.1(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 117.8(2) . . ?
C18 C19 H19 121.1 . . ?
C20 C19 H19 121.1 . . ?
C15 C20 C19 121.3(2) . . ?
C15 C20 C21 109.20(16) . . ?
C19 C20 C21 129.47(19) . . ?
O3 C21 N1 125.8(2) . . ?
O3 C21 C20 128.37(19) . . ?
N1 C21 C20 105.83(16) . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        33.63
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.075
