# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1052879'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O2'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43

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   P21/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                   15.4693(8)
_cell_length_b                   7.1860(3)
_cell_length_c                   17.5613(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.307(5)
_cell_angle_gamma                90.00
_cell_volume                     1818.72(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2831
_cell_measurement_theta_min      3.2120
_cell_measurement_theta_max      27.9550

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97860
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'w scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14288
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0516
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.33
_reflns_number_total             4340
_reflns_number_gt                2512
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   11.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   19.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -80.00  -47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955 -179.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   22.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   39.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -57.0000  120.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   -1.00   28.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673   57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  7 omega  -51.00   38.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -77.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
  8 omega  -39.00   36.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7673  -57.0000 -120.0000 75

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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 > 2σ(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)+(0.0511P)²+0.2511P] 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     SHELXL
_refine_ls_extinction_coef       0.0169(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4340
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0516
_refine_ls_wR_factor_ref         0.1368
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
C1 C 0.59520(12) 0.8587(2) 0.15148(10) 0.0433(4) Uani 1 1 d . . .
C2 C 0.52838(12) 0.8018(2) 0.07577(10) 0.0398(4) Uani 1 1 d . . .
C3 C 0.55748(12) 0.7409(2) 0.01213(11) 0.0423(4) Uani 1 1 d . . .
C4 C 0.49314(14) 0.6964(2) -0.06307(11) 0.0492(5) Uani 1 1 d . . .
H4 H 0.5127 0.6555 -0.1044 0.059 Uiso 1 1 calc R . .
C5 C 0.39895(14) 0.7122(2) -0.07775(11) 0.0516(5) Uani 1 1 d . . .
H5 H 0.3559 0.6834 -0.1292 0.062 Uiso 1 1 calc R . .
C6 C 0.36868(13) 0.7696(2) -0.01745(10) 0.0457(4) Uani 1 1 d . . .
H6 H 0.3053 0.7806 -0.0287 0.055 Uiso 1 1 calc R . .
C7 C 0.43223(12) 0.8126(2) 0.06184(10) 0.0399(4) Uani 1 1 d . . .
C8 C 0.40384(12) 0.8810(2) 0.12624(10) 0.0431(4) Uani 1 1 d . . .
C9 C 0.47179(13) 0.9386(3) 0.19834(11) 0.0506(5) Uani 1 1 d . . .
H9 H 0.4541 0.9868 0.2396 0.061 Uiso 1 1 calc R . .
C10 C 0.56540(13) 0.9268(3) 0.21092(11) 0.0507(5) Uani 1 1 d . . .
H10 H 0.6089 0.9657 0.2606 0.061 Uiso 1 1 calc R . .
C11 C 0.69408(13) 0.8579(2) 0.16483(12) 0.0506(5) Uani 1 1 d . . .
C12 C 0.65692(14) 0.7304(2) 0.02571(13) 0.0505(5) Uani 1 1 d . . .
C13 C 0.25414(14) 0.7264(3) 0.09958(12) 0.0569(5) Uani 1 1 d . . .
H13A H 0.2625 0.6698 0.1519 0.068 Uiso 1 1 calc R . .
H13B H 0.2750 0.6386 0.0680 0.068 Uiso 1 1 calc R . .
C14 C 0.15255(14) 0.7706(3) 0.05475(14) 0.0682(6) Uani 1 1 d . . .
H14A H 0.1162 0.6576 0.0480 0.082 Uiso 1 1 calc R . .
H14B H 0.1437 0.8188 0.0008 0.082 Uiso 1 1 calc R . .
C15 C 0.11914(15) 0.9131(4) 0.10169(13) 0.0711(6) Uani 1 1 d . . .
H15A H 0.0564 0.9511 0.0690 0.085 Uiso 1 1 calc R . .
H15B H 0.1181 0.8573 0.1516 0.085 Uiso 1 1 calc R . .
C16 C 0.18145(14) 1.0812(3) 0.12244(13) 0.0673(6) Uani 1 1 d . . .
H16A H 0.1730 1.1501 0.0728 0.081 Uiso 1 1 calc R . .
H16B H 0.1636 1.1617 0.1585 0.081 Uiso 1 1 calc R . .
C17 C 0.28261(13) 1.0304(3) 0.16317(12) 0.0610(6) Uani 1 1 d . . .
H17A H 0.3204 1.1416 0.1713 0.073 Uiso 1 1 calc R . .
H17B H 0.2931 0.9756 0.2163 0.073 Uiso 1 1 calc R . .
C18 C 0.81711(13) 0.7934(3) 0.11102(14) 0.0607(5) Uani 1 1 d . . .
H18A H 0.8496 0.8804 0.1542 0.073 Uiso 1 1 calc R . .
H18B H 0.8223 0.8390 0.0609 0.073 Uiso 1 1 calc R . .
C19 C 0.86515(12) 0.6073(3) 0.13121(11) 0.0476(5) Uani 1 1 d . . .
C20 C 0.94669(13) 0.5867(3) 0.11938(14) 0.0636(6) Uani 1 1 d . . .
H20 H 0.9692 0.6814 0.0956 0.076 Uiso 1 1 calc R . .
C21 C 0.99476(16) 0.4255(4) 0.14293(17) 0.0865(8) Uani 1 1 d . . .
H21 H 1.0514 0.4106 0.1365 0.104 Uiso 1 1 calc R . .
C22 C 0.96053(18) 0.2858(4) 0.17583(14) 0.0770(7) Uani 1 1 d . . .
H22 H 0.9928 0.1745 0.1916 0.092 Uiso 1 1 calc R . .
C23 C 0.87786(17) 0.3127(3) 0.18521(13) 0.0662(6) Uani 1 1 d . . .
H23 H 0.8541 0.2169 0.2074 0.079 Uiso 1 1 calc R . .
N1 N 0.82839(12) 0.4732(2) 0.16362(10) 0.0621(5) Uani 1 1 d . . .
N2 N 0.71932(10) 0.7924(2) 0.10104(10) 0.0509(4) Uani 1 1 d . . .
N3 N 0.30931(10) 0.8980(2) 0.11232(9) 0.0488(4) Uani 1 1 d . . .
O1 O 0.68586(10) 0.67318(19) -0.02607(9) 0.0658(4) Uani 1 1 d . . .
O2 O 0.75400(9) 0.9144(2) 0.22763(9) 0.0689(4) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C10 1.375(2) . ?
C1 C2 1.416(2) . ?
C1 C11 1.461(2) . ?
C2 C3 1.417(2) . ?
C2 C7 1.419(2) . ?
C3 C4 1.372(2) . ?
C3 C12 1.470(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.368(2) . ?
C6 C7 1.416(2) . ?
C7 C8 1.440(2) . ?
C8 C9 1.383(2) . ?
C8 N3 1.398(2) . ?
C9 C10 1.386(2) . ?
C11 O2 1.224(2) . ?
C11 N2 1.395(2) . ?
C12 O1 1.222(2) . ?
C12 N2 1.397(2) . ?
C13 N3 1.469(2) . ?
C13 C14 1.514(3) . ?
C14 C15 1.518(3) . ?
C15 C16 1.505(3) . ?
C16 C17 1.510(3) . ?
C17 N3 1.464(2) . ?
C18 N2 1.458(2) . ?
C18 C19 1.508(3) . ?
C19 N1 1.346(2) . ?
C19 C20 1.359(2) . ?
C20 C21 1.357(3) . ?
C21 C22 1.358(3) . ?
C22 C23 1.361(3) . ?
C23 N1 1.359(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
C10 C1 C2 118.95(16) . . ?
C10 C1 C11 119.99(17) . . ?
C2 C1 C11 120.93(16) . . ?
C1 C2 C3 119.81(16) . . ?
C1 C2 C7 120.51(15) . . ?
C3 C2 C7 119.62(16) . . ?
C4 C3 C2 120.26(16) . . ?
C4 C3 C12 119.64(16) . . ?
C2 C3 C12 120.08(17) . . ?
C3 C4 C5 120.33(16) . . ?
C6 C5 C4 120.79(17) . . ?
C5 C6 C7 121.08(17) . . ?
C6 C7 C2 117.85(15) . . ?
C6 C7 C8 123.06(16) . . ?
C2 C7 C8 118.88(15) . . ?
C9 C8 N3 122.20(16) . . ?
C9 C8 C7 118.29(16) . . ?
N3 C8 C7 119.39(15) . . ?
C10 C9 C8 122.02(17) . . ?
C1 C10 C9 121.32(17) . . ?
O2 C11 N2 119.62(17) . . ?
O2 C11 C1 123.32(18) . . ?
N2 C11 C1 117.04(17) . . ?
O1 C12 N2 119.87(18) . . ?
O1 C12 C3 122.77(19) . . ?
N2 C12 C3 117.35(16) . . ?
N3 C13 C14 109.81(17) . . ?
C13 C14 C15 110.66(17) . . ?
C16 C15 C14 111.00(17) . . ?
C17 C16 C15 112.53(19) . . ?
N3 C17 C16 109.97(16) . . ?
N2 C18 C19 115.16(15) . . ?
N1 C19 C20 123.00(18) . . ?
N1 C19 C18 119.11(16) . . ?
C20 C19 C18 117.80(17) . . ?
C21 C20 C19 118.9(2) . . ?
C20 C21 C22 120.3(2) . . ?
C21 C22 C23 118.4(2) . . ?
N1 C23 C22 123.0(2) . . ?
C19 N1 C23 116.35(18) . . ?
C11 N2 C12 124.68(16) . . ?
C11 N2 C18 118.86(17) . . ?
C12 N2 C18 116.42(16) . . ?
C8 N3 C17 117.35(15) . . ?
C8 N3 C13 117.78(14) . . ?
C17 N3 C13 111.19(15) . . ?

_diffrn_measured_fraction_theta_max 0.871
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_[(2)2(I2F4)]
_database_code_depnum_ccdc_archive 'CCDC 1052880'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            'XB co-crystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'c23 h21 n3 o2 * c3 f2 i1'
_chemical_formula_sum            'C26 H21 F2 I N3 O2'
_chemical_formula_weight         572.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   5.1722(4)
_cell_length_b                   11.5170(11)
_cell_length_c                   38.904(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.669(7)
_cell_angle_gamma                90.00
_cell_volume                     2312.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2053
_cell_measurement_theta_min      3.1630
_cell_measurement_theta_max      25.5430

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.002
_exptl_crystal_size_min          0.001
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    1.430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.45366
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            25307
_diffrn_reflns_av_R_equivalents  0.1732
_diffrn_reflns_av_sigmaI/netI    0.2175
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         30.07
_reflns_number_total             6047
_reflns_number_gt                2291
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   23.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -17.00   10.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -21.00    7.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142  -99.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega    9.00   45.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3142   38.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega  -45.00    3.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642  -57.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega    2.00   84.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   57.0000 -120.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   60.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642  -99.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   87.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   57.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
  9 omega   30.00   92.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   19.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
 10 omega  -24.00    7.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5642   19.0000   90.0000 31

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR-92 (altomare giacovazzo 92)'
_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 > 2σ(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)+(0.0131P)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         6047
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2418
_refine_ls_R_factor_gt           0.0836
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_restrained_S_all      0.970
_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
C1 C 0.6306(13) 0.0863(5) 0.76028(18) 0.0442(19) Uani 1 1 d . . .
H1 H 0.5121 0.0353 0.7690 0.053 Uiso 1 1 calc R . .
C2 C 0.7791(12) 0.1548(5) 0.78234(18) 0.0363(17) Uani 1 1 d . . .
C3 C 0.9692(13) 0.2280(5) 0.76931(18) 0.0386(18) Uani 1 1 d . . .
C4 C 1.1311(13) 0.2960(5) 0.79177(19) 0.0412(18) Uani 1 1 d . . .
C5 C 1.3239(13) 0.3635(6) 0.7791(2) 0.055(2) Uani 1 1 d . . .
H5 H 1.4271 0.4102 0.7939 0.066 Uiso 1 1 calc R . .
C6 C 1.3628(13) 0.3612(6) 0.7440(2) 0.055(2) Uani 1 1 d . . .
H6 H 1.4980 0.4038 0.7357 0.067 Uiso 1 1 calc R . .
C7 C 1.2052(12) 0.2974(6) 0.72175(19) 0.051(2) Uani 1 1 d . . .
H7 H 1.2338 0.2976 0.6984 0.061 Uiso 1 1 calc R . .
C8 C 1.0010(12) 0.2315(5) 0.73362(19) 0.0387(18) Uani 1 1 d . . .
C9 C 0.8306(13) 0.1649(6) 0.71079(19) 0.0435(18) Uani 1 1 d . . .
C10 C 0.6541(13) 0.0918(5) 0.72462(18) 0.0453(19) Uani 1 1 d . . .
H10 H 0.5487 0.0453 0.7101 0.054 Uiso 1 1 calc R . .
C11 C 0.7289(14) 0.1581(6) 0.8187(2) 0.047(2) Uani 1 1 d . . .
C12 C 1.0894(14) 0.3001(6) 0.8287(2) 0.048(2) Uani 1 1 d . . .
C13 C 0.8137(14) 0.2487(6) 0.87560(18) 0.058(2) Uani 1 1 d . . .
H13A H 0.6274 0.2587 0.8754 0.070 Uiso 1 1 calc R . .
H13B H 0.8929 0.3196 0.8847 0.070 Uiso 1 1 calc R . .
C14 C 0.8890(13) 0.1522(5) 0.89957(19) 0.0432(19) Uani 1 1 d . . .
C15 C 1.0908(13) 0.0757(6) 0.89495(19) 0.054(2) Uani 1 1 d . . .
H15 H 1.1849 0.0803 0.8754 0.064 Uiso 1 1 calc R . .
C16 C 1.1493(14) -0.0061(6) 0.9194(2) 0.060(2) Uani 1 1 d . . .
H16 H 1.2846 -0.0579 0.9167 0.073 Uiso 1 1 calc R . .
C17 C 1.0091(17) -0.0121(7) 0.9479(2) 0.074(3) Uani 1 1 d . . .
H17 H 1.0434 -0.0681 0.9648 0.089 Uiso 1 1 calc R . .
C18 C 0.8149(15) 0.0683(7) 0.9505(2) 0.069(3) Uani 1 1 d . . .
H18 H 0.7201 0.0654 0.9700 0.083 Uiso 1 1 calc R . .
C19 C 0.7838(13) 0.2936(6) 0.66102(18) 0.054(2) Uani 1 1 d . . .
H19A H 0.8524 0.3528 0.6768 0.065 Uiso 1 1 calc R . .
H19B H 0.5970 0.3028 0.6586 0.065 Uiso 1 1 calc R . .
C20 C 0.8941(14) 0.3105(7) 0.62656(19) 0.067(2) Uani 1 1 d . . .
H20A H 1.0817 0.3064 0.6291 0.080 Uiso 1 1 calc R . .
H20B H 0.8461 0.3865 0.6175 0.080 Uiso 1 1 calc R . .
C21 C 0.7916(17) 0.2172(8) 0.6016(2) 0.089(3) Uani 1 1 d . . .
H21A H 0.6071 0.2281 0.5966 0.107 Uiso 1 1 calc R . .
H21B H 0.8764 0.2238 0.5802 0.107 Uiso 1 1 calc R . .
C22 C 0.8408(16) 0.0977(7) 0.6169(2) 0.086(3) Uani 1 1 d . . .
H22A H 1.0256 0.0825 0.6188 0.104 Uiso 1 1 calc R . .
H22B H 0.7590 0.0396 0.6018 0.104 Uiso 1 1 calc R . .
C23 C 0.7336(16) 0.0884(6) 0.6527(2) 0.075(3) Uani 1 1 d . . .
H23A H 0.5466 0.0969 0.6507 0.090 Uiso 1 1 calc R . .
H23B H 0.7739 0.0125 0.6624 0.090 Uiso 1 1 calc R . .
C24 C 0.0239(15) 0.3872(6) 1.0084(2) 0.054(2) Uani 1 1 d . . .
C25 C 0.1629(13) 0.4260(7) 0.98200(19) 0.051(2) Uani 1 1 d . . .
C26 C 0.1323(13) 0.5413(7) 0.97454(18) 0.054(2) Uani 1 1 d . . .
N1 N 0.7530(11) 0.1493(5) 0.92737(17) 0.0591(18) Uani 1 1 d . . .
N2 N 0.8838(12) 0.2346(5) 0.84014(15) 0.0486(16) Uani 1 1 d . . .
N3 N 0.8467(11) 0.1784(5) 0.67538(15) 0.0559(16) Uani 1 1 d . . .
O1 O 0.5628(9) 0.1006(4) 0.83190(13) 0.0659(16) Uani 1 1 d . . .
O2 O 1.2184(10) 0.3599(4) 0.84894(14) 0.0705(16) Uani 1 1 d . . .
F1 F 0.0454(9) 0.2747(4) 1.01731(12) 0.0916(16) Uani 1 1 d . . .
F2 F 0.2662(9) 0.5882(4) 0.94865(12) 0.0922(16) Uani 1 1 d . . .
I001 I 0.40430(10) 0.31777(5) 0.955356(14) 0.0653(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.365(8) . ?
C1 C10 1.402(8) . ?
C2 C3 1.413(8) . ?
C2 C11 1.455(9) . ?
C3 C4 1.409(8) . ?
C3 C8 1.409(8) . ?
C4 C5 1.380(8) . ?
C4 C12 1.466(9) . ?
C5 C6 1.391(9) . ?
C6 C7 1.366(9) . ?
C7 C8 1.403(8) . ?
C8 C9 1.434(8) . ?
C9 C10 1.376(8) . ?
C9 N3 1.394(8) . ?
C11 O1 1.223(7) . ?
C11 N2 1.424(8) . ?
C12 O2 1.213(7) . ?
C12 N2 1.400(8) . ?
C13 N2 1.458(7) . ?
C13 C14 1.486(8) . ?
C14 N1 1.328(8) . ?
C14 C15 1.387(8) . ?
C15 C16 1.359(9) . ?
C16 C17 1.364(9) . ?
C17 C18 1.375(9) . ?
C18 N1 1.322(9) . ?
C19 N3 1.469(7) . ?
C19 C20 1.503(8) . ?
C20 C21 1.520(9) . ?
C21 C22 1.514(9) . ?
C22 C23 1.534(9) . ?
C23 N3 1.460(8) . ?
C24 F1 1.344(7) . ?
C24 C26 1.357(9) 3_567 ?
C24 C25 1.367(9) . ?
C25 C26 1.366(9) . ?
C25 I001 2.087(7) . ?
C26 C24 1.357(9) 3_567 ?
C26 F2 1.370(7) . ?

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
C2 C1 C10 121.0(6) . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 C11 119.9(7) . . ?
C3 C2 C11 120.3(7) . . ?
C4 C3 C8 119.5(6) . . ?
C4 C3 C2 120.6(7) . . ?
C8 C3 C2 119.9(7) . . ?
C5 C4 C3 120.4(7) . . ?
C5 C4 C12 119.1(7) . . ?
C3 C4 C12 120.4(7) . . ?
C4 C5 C6 119.5(7) . . ?
C7 C6 C5 121.0(7) . . ?
C6 C7 C8 120.9(7) . . ?
C7 C8 C3 118.6(7) . . ?
C7 C8 C9 122.1(7) . . ?
C3 C8 C9 119.3(6) . . ?
C10 C9 N3 122.5(7) . . ?
C10 C9 C8 118.8(7) . . ?
N3 C9 C8 118.6(6) . . ?
C9 C10 C1 121.1(7) . . ?
O1 C11 N2 118.2(7) . . ?
O1 C11 C2 124.6(7) . . ?
N2 C11 C2 117.2(7) . . ?
O2 C12 N2 119.8(7) . . ?
O2 C12 C4 123.0(7) . . ?
N2 C12 C4 117.2(7) . . ?
N2 C13 C14 116.1(6) . . ?
N1 C14 C15 122.1(7) . . ?
N1 C14 C13 113.5(6) . . ?
C15 C14 C13 124.3(7) . . ?
C16 C15 C14 119.1(7) . . ?
C15 C16 C17 119.8(7) . . ?
C16 C17 C18 117.1(8) . . ?
N1 C18 C17 124.8(8) . . ?
N3 C19 C20 111.6(6) . . ?
C19 C20 C21 109.9(6) . . ?
C22 C21 C20 110.4(7) . . ?
C21 C22 C23 111.0(6) . . ?
N3 C23 C22 110.2(6) . . ?
F1 C24 C26 120.1(8) . 3_567 ?
F1 C24 C25 118.1(8) . . ?
C26 C24 C25 121.8(7) 3_567 . ?
C26 C25 C24 114.7(7) . . ?
C26 C25 I001 122.7(6) . . ?
C24 C25 I001 122.6(6) . . ?
C24 C26 C25 123.4(7) 3_567 . ?
C24 C26 F2 117.7(8) 3_567 . ?
C25 C26 F2 118.9(7) . . ?
C18 N1 C14 117.1(6) . . ?
C12 N2 C11 123.9(6) . . ?
C12 N2 C13 118.8(6) . . ?
C11 N2 C13 117.3(6) . . ?
C9 N3 C23 118.1(6) . . ?
C9 N3 C19 116.8(6) . . ?
C23 N3 C19 109.9(6) . . ?

_diffrn_measured_fraction_theta_max 0.889
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.508
_refine_diff_density_rms         0.092
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1052881'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H42 N6 O4'
_chemical_formula_weight         742.86

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   Pc

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

_cell_length_a                   12.4319(13)
_cell_length_b                   4.7462(5)
_cell_length_c                   31.791(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.259(9)
_cell_angle_gamma                90.00
_cell_volume                     1845.8(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1022
_cell_measurement_theta_min      3.3300
_cell_measurement_theta_max      23.5730

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9064
_diffrn_reflns_av_R_equivalents  0.0850
_diffrn_reflns_av_sigmaI/netI    0.1568
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         29.23
_reflns_number_total             5435
_reflns_number_gt                2027
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   17.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   15.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  120.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   15.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.5955  -99.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega   12.00   83.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6892    0.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00    0.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6892    0.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   29.00   1.0000  400.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6892  -38.0000 -150.0000 28

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2005)'
_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 > 2σ(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)+(0.0520P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(3)
_refine_ls_number_reflns         5435
_refine_ls_number_parameters     506
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.2153
_refine_ls_R_factor_gt           0.0640
_refine_ls_wR_factor_ref         0.1782
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_restrained_S_all      0.969
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.003

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
C1 C -0.1721(7) 0.1462(18) -0.0627(2) 0.043(2) Uani 1 1 d . . .
C2 C -0.1133(7) 0.0161(17) -0.0912(2) 0.042(2) Uani 1 1 d . . .
C3 C -0.0337(7) -0.1904(19) -0.0774(3) 0.048(2) Uani 1 1 d . . .
C4 C 0.0240(7) -0.3048(18) -0.1059(3) 0.052(2) Uani 1 1 d . . .
H4 H 0.0788 -0.4347 -0.0962 0.062 Uiso 1 1 calc R . .
C5 C 0.0035(7) -0.2340(18) -0.1487(3) 0.056(2) Uani 1 1 d . . .
H5 H 0.0426 -0.3199 -0.1675 0.067 Uiso 1 1 calc R . .
C6 C -0.0757(7) -0.0339(17) -0.1635(2) 0.048(2) Uani 1 1 d . . .
C7 C -0.1363(7) 0.0980(18) -0.1353(2) 0.045(2) Uani 1 1 d . . .
C8 C -0.2139(7) 0.3073(18) -0.1479(3) 0.050(2) Uani 1 1 d . . .
H8 H -0.2278 0.3669 -0.1762 0.060 Uiso 1 1 calc R . .
C9 C -0.2697(7) 0.4255(18) -0.1193(3) 0.057(3) Uani 1 1 d . . .
H9 H -0.3228 0.5609 -0.1285 0.069 Uiso 1 1 calc R . .
C10 C -0.2488(7) 0.3474(17) -0.0766(3) 0.054(2) Uani 1 1 d . . .
H10 H -0.2870 0.4322 -0.0574 0.065 Uiso 1 1 calc R . .
C11 C -0.1516(7) 0.067(2) -0.0173(3) 0.053(2) Uani 1 1 d . . .
C12 C -0.0114(8) -0.281(2) -0.0321(3) 0.054(3) Uani 1 1 d . . .
C13 C -0.2032(7) -0.071(2) -0.2299(3) 0.066(3) Uani 1 1 d . . .
H13A H -0.2595 -0.0386 -0.2129 0.079 Uiso 1 1 calc R . .
H13B H -0.1957 -0.2733 -0.2331 0.079 Uiso 1 1 calc R . .
C14 C -0.0114(7) -0.0056(19) -0.2324(2) 0.064(3) Uani 1 1 d . . .
H14A H -0.0013 -0.2068 -0.2354 0.076 Uiso 1 1 calc R . .
H14B H 0.0564 0.0726 -0.2170 0.076 Uiso 1 1 calc R . .
C15 C -0.0387(8) 0.129(2) -0.2760(3) 0.079(3) Uani 1 1 d . . .
H15A H -0.0420 0.3316 -0.2727 0.095 Uiso 1 1 calc R . .
H15B H 0.0189 0.0869 -0.2920 0.095 Uiso 1 1 calc R . .
C16 C -0.1456(8) 0.026(2) -0.3005(3) 0.082(3) Uani 1 1 d . . .
H16A H -0.1394 -0.1717 -0.3076 0.099 Uiso 1 1 calc R . .
H16B H -0.1640 0.1306 -0.3270 0.099 Uiso 1 1 calc R . .
C17 C -0.2367(8) 0.064(2) -0.2737(3) 0.080(3) Uani 1 1 d . . .
H17A H -0.2505 0.2627 -0.2704 0.096 Uiso 1 1 calc R . .
H17B H -0.3036 -0.0228 -0.2885 0.096 Uiso 1 1 calc R . .
C18 C -0.0562(8) -0.2414(19) 0.0401(2) 0.070(3) Uani 1 1 d . . .
H18A H -0.0232 -0.4273 0.0421 0.084 Uiso 1 1 calc R . .
H18B H -0.1265 -0.2562 0.0491 0.084 Uiso 1 1 calc R . .
C19 C -0.0269(10) 0.103(2) 0.0997(3) 0.091(4) Uani 1 1 d . . .
H19 H -0.1009 0.0839 0.1006 0.110 Uiso 1 1 calc R . .
C20 C 0.0159(10) -0.044(2) 0.0696(3) 0.066(3) Uani 1 1 d . . .
C21 C 0.1207(11) -0.011(3) 0.0690(3) 0.115(5) Uani 1 1 d . . .
H21 H 0.1508 -0.1097 0.0486 0.138 Uiso 1 1 calc R . .
C22 C 0.1876(11) 0.162(4) 0.0964(4) 0.140(6) Uani 1 1 d . . .
H22 H 0.2608 0.1886 0.0947 0.167 Uiso 1 1 calc R . .
C23 C 0.142(2) 0.285(4) 0.1253(5) 0.169(11) Uani 1 1 d . . .
H23 H 0.1886 0.3892 0.1456 0.202 Uiso 1 1 calc R . .
N1 N 0.0373(17) 0.283(4) 0.1296(5) 0.177(8) Uani 1 1 d . . .
N2 N -0.0730(6) -0.1450(16) -0.0051(2) 0.057(2) Uani 1 1 d . . .
N3 N -0.1001(6) 0.0453(15) -0.2080(2) 0.056(2) Uani 1 1 d . . .
O1 O -0.1998(5) 0.1632(13) 0.00964(18) 0.0719(19) Uani 1 1 d . . .
O2 O 0.0575(5) -0.4534(15) -0.01814(19) 0.078(2) Uani 1 1 d . . .
C24 C 0.4620(8) 0.6987(17) -0.0818(3) 0.046(2) Uani 1 1 d . . .
C25 C 0.3963(7) 0.4903(18) -0.0665(2) 0.041(2) Uani 1 1 d . . .
C26 C 0.3104(7) 0.3629(19) -0.0936(2) 0.044(2) Uani 1 1 d . . .
C27 C 0.2499(7) 0.1584(19) -0.0785(3) 0.055(2) Uani 1 1 d . . .
H27 H 0.1940 0.0700 -0.0972 0.066 Uiso 1 1 calc R . .
C28 C 0.2704(6) 0.0810(18) -0.0360(3) 0.052(2) Uani 1 1 d . . .
H28 H 0.2279 -0.0574 -0.0263 0.062 Uiso 1 1 calc R . .
C29 C 0.3539(6) 0.2085(18) -0.0079(2) 0.047(2) Uani 1 1 d . . .
H29 H 0.3677 0.1535 0.0207 0.056 Uiso 1 1 calc R . .
C30 C 0.4193(6) 0.4242(16) -0.0222(2) 0.038(2) Uani 1 1 d . . .
C31 C 0.5074(7) 0.5619(18) 0.0051(3) 0.049(2) Uani 1 1 d . . .
C32 C 0.5694(7) 0.7525(19) -0.0117(2) 0.054(3) Uani 1 1 d . . .
H32 H 0.6280 0.8377 0.0060 0.064 Uiso 1 1 calc R . .
C33 C 0.5465(7) 0.8234(17) -0.0552(3) 0.052(2) Uani 1 1 d . . .
H33 H 0.5894 0.9565 -0.0660 0.062 Uiso 1 1 calc R . .
C34 C 0.4378(8) 0.7794(19) -0.1276(3) 0.054(2) Uani 1 1 d . . .
C35 C 0.2861(8) 0.449(2) -0.1392(3) 0.055(3) Uani 1 1 d . . .
C36 C 0.6388(7) 0.5399(19) 0.0723(3) 0.068(3) Uani 1 1 d . . .
H36A H 0.6504 0.7417 0.0750 0.081 Uiso 1 1 calc R . .
H36B H 0.6912 0.4636 0.0561 0.081 Uiso 1 1 calc R . .
C37 C 0.4472(7) 0.6055(19) 0.0734(2) 0.062(3) Uani 1 1 d . . .
H37A H 0.3735 0.5742 0.0581 0.074 Uiso 1 1 calc R . .
H37B H 0.4590 0.8071 0.0762 0.074 Uiso 1 1 calc R . .
C38 C 0.6566(8) 0.4082(19) 0.1162(3) 0.077(3) Uani 1 1 d . . .
H38A H 0.7302 0.4494 0.1309 0.093 Uiso 1 1 calc R . .
H38B H 0.6491 0.2053 0.1134 0.093 Uiso 1 1 calc R . .
C39 C 0.4600(8) 0.473(2) 0.1177(2) 0.071(3) Uani 1 1 d . . .
H39A H 0.4075 0.5554 0.1333 0.085 Uiso 1 1 calc R . .
H39B H 0.4454 0.2720 0.1150 0.085 Uiso 1 1 calc R . .
C40 C 0.5747(9) 0.520(2) 0.1421(3) 0.086(3) Uani 1 1 d . . .
H40A H 0.5840 0.4242 0.1694 0.103 Uiso 1 1 calc R . .
H40B H 0.5869 0.7200 0.1474 0.103 Uiso 1 1 calc R . .
C41 C 0.3219(8) 0.7345(19) -0.1984(3) 0.063(3) Uani 1 1 d . . .
H41A H 0.3582 0.9108 -0.2024 0.076 Uiso 1 1 calc R . .
H41B H 0.2438 0.7677 -0.2052 0.076 Uiso 1 1 calc R . .
C42 C 0.3512(10) 0.526(2) -0.2286(3) 0.067(3) Uani 1 1 d . . .
C43 C 0.2777(9) 0.412(2) -0.2613(3) 0.085(4) Uani 1 1 d . . .
H43 H 0.2048 0.4672 -0.2650 0.103 Uiso 1 1 calc R . .
C44 C 0.4567(11) 0.434(3) -0.2274(3) 0.089(4) Uani 1 1 d . . .
H44 H 0.5100 0.5056 -0.2058 0.107 Uiso 1 1 calc R . .
C45 C 0.4884(16) 0.256(4) -0.2538(5) 0.134(7) Uani 1 1 d . . .
H45 H 0.5619 0.2091 -0.2509 0.161 Uiso 1 1 calc R . .
C46 C 0.420(2) 0.149(4) -0.2832(6) 0.184(15) Uani 1 1 d . . .
H46 H 0.4446 0.0206 -0.3016 0.220 Uiso 1 1 calc R . .
N4 N 0.5258(5) 0.4833(13) 0.04921(19) 0.0489(19) Uani 1 1 d . . .
N5 N 0.3506(6) 0.6531(15) -0.1533(2) 0.0498(19) Uani 1 1 d . . .
N6 N 0.3101(16) 0.215(3) -0.2891(3) 0.149(6) Uani 1 1 d . . .
O3 O 0.2094(5) 0.3402(13) -0.16439(17) 0.0655(18) Uani 1 1 d . . .
O4 O 0.4941(6) 0.9494(15) -0.14299(18) 0.084(2) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C10 1.366(10) . ?
C1 C2 1.404(10) . ?
C1 C11 1.469(10) . ?
C2 C3 1.406(11) . ?
C2 C7 1.436(9) . ?
C3 C4 1.365(10) . ?
C3 C12 1.478(11) . ?
C4 C5 1.381(10) . ?
C5 C6 1.389(11) . ?
C6 C7 1.415(10) . ?
C6 N3 1.441(9) . ?
C7 C8 1.393(11) . ?
C8 C9 1.360(11) . ?
C9 C10 1.386(11) . ?
C11 O1 1.218(9) . ?
C11 N2 1.408(10) . ?
C12 O2 1.211(10) . ?
C12 N2 1.407(11) . ?
C13 N3 1.454(10) . ?
C13 C17 1.523(11) . ?
C14 N3 1.477(9) . ?
C14 C15 1.508(10) . ?
C15 C16 1.498(11) . ?
C16 C17 1.544(10) . ?
C18 N2 1.486(10) . ?
C18 C20 1.503(11) . ?
C19 C20 1.366(14) . ?
C19 N1 1.415(19) . ?
C20 C21 1.316(14) . ?
C21 C22 1.366(15) . ?
C22 C23 1.30(2) . ?
C23 N1 1.33(2) . ?
C24 C33 1.361(10) . ?
C24 C25 1.422(10) . ?
C24 C34 1.484(10) . ?
C25 C26 1.385(10) . ?
C25 C30 1.422(9) . ?
C26 C27 1.366(10) . ?
C26 C35 1.486(11) . ?
C27 C28 1.379(10) . ?
C28 C29 1.384(10) . ?
C29 C30 1.432(10) . ?
C30 C31 1.429(10) . ?
C31 C32 1.357(10) . ?
C31 N4 1.429(9) . ?
C32 C33 1.404(10) . ?
C34 O4 1.225(9) . ?
C34 N5 1.373(10) . ?
C35 O3 1.242(9) . ?
C35 N5 1.382(10) . ?
C36 N4 1.489(10) . ?
C36 C38 1.507(10) . ?
C37 N4 1.466(9) . ?
C37 C39 1.527(10) . ?
C38 C40 1.516(12) . ?
C39 C40 1.514(12) . ?
C41 N5 1.467(9) . ?
C41 C42 1.471(12) . ?
C42 C43 1.365(13) . ?
C42 C44 1.375(13) . ?
C43 N6 1.396(15) . ?
C44 C45 1.299(16) . ?
C45 C46 1.25(3) . ?
C46 N6 1.39(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
C10 C1 C2 120.9(8) . . ?
C10 C1 C11 119.0(8) . . ?
C2 C1 C11 120.1(8) . . ?
C1 C2 C3 121.6(8) . . ?
C1 C2 C7 118.4(7) . . ?
C3 C2 C7 120.0(8) . . ?
C4 C3 C2 119.6(9) . . ?
C4 C3 C12 120.0(8) . . ?
C2 C3 C12 120.4(8) . . ?
C3 C4 C5 122.1(8) . . ?
C4 C5 C6 119.8(8) . . ?
C5 C6 C7 120.8(8) . . ?
C5 C6 N3 121.6(8) . . ?
C7 C6 N3 117.6(8) . . ?
C8 C7 C6 123.6(7) . . ?
C8 C7 C2 118.7(7) . . ?
C6 C7 C2 117.7(8) . . ?
C9 C8 C7 120.8(8) . . ?
C8 C9 C10 121.0(8) . . ?
C1 C10 C9 120.1(8) . . ?
O1 C11 N2 118.5(8) . . ?
O1 C11 C1 125.0(9) . . ?
N2 C11 C1 116.4(8) . . ?
O2 C12 N2 120.8(9) . . ?
O2 C12 C3 123.5(9) . . ?
N2 C12 C3 115.7(8) . . ?
N3 C13 C17 110.6(8) . . ?
N3 C14 C15 110.2(7) . . ?
C16 C15 C14 112.0(8) . . ?
C15 C16 C17 110.1(8) . . ?
C13 C17 C16 110.4(8) . . ?
N2 C18 C20 112.1(7) . . ?
C20 C19 N1 122.4(14) . . ?
C21 C20 C19 117.3(10) . . ?
C21 C20 C18 123.1(11) . . ?
C19 C20 C18 119.5(11) . . ?
C20 C21 C22 123.7(13) . . ?
C23 C22 C21 115.3(15) . . ?
C22 C23 N1 129(2) . . ?
C23 N1 C19 112(2) . . ?
C12 N2 C11 125.8(7) . . ?
C12 N2 C18 116.9(8) . . ?
C11 N2 C18 117.3(8) . . ?
C6 N3 C13 112.6(7) . . ?
C6 N3 C14 115.2(7) . . ?
C13 N3 C14 111.3(7) . . ?
C33 C24 C25 121.1(8) . . ?
C33 C24 C34 119.8(8) . . ?
C25 C24 C34 119.1(8) . . ?
C26 C25 C24 121.2(7) . . ?
C26 C25 C30 121.0(7) . . ?
C24 C25 C30 117.7(7) . . ?
C27 C26 C25 120.3(8) . . ?
C27 C26 C35 120.5(8) . . ?
C25 C26 C35 119.1(8) . . ?
C26 C27 C28 121.0(8) . . ?
C27 C28 C29 120.3(8) . . ?
C28 C29 C30 120.6(7) . . ?
C25 C30 C31 119.9(7) . . ?
C25 C30 C29 116.6(7) . . ?
C31 C30 C29 123.4(7) . . ?
C32 C31 N4 123.8(8) . . ?
C32 C31 C30 119.5(7) . . ?
N4 C31 C30 116.7(8) . . ?
C31 C32 C33 121.2(8) . . ?
C24 C33 C32 120.4(8) . . ?
O4 C34 N5 119.8(8) . . ?
O4 C34 C24 122.1(9) . . ?
N5 C34 C24 118.1(9) . . ?
O3 C35 N5 120.4(8) . . ?
O3 C35 C26 121.0(9) . . ?
N5 C35 C26 118.6(8) . . ?
N4 C36 C38 110.6(8) . . ?
N4 C37 C39 110.6(7) . . ?
C36 C38 C40 110.8(8) . . ?
C40 C39 C37 110.1(8) . . ?
C39 C40 C38 109.4(8) . . ?
N5 C41 C42 114.6(7) . . ?
C43 C42 C44 113.8(10) . . ?
C43 C42 C41 123.5(11) . . ?
C44 C42 C41 122.7(10) . . ?
C42 C43 N6 121.1(12) . . ?
C45 C44 C42 125.8(13) . . ?
C46 C45 C44 120(2) . . ?
C45 C46 N6 122(2) . . ?
C31 N4 C37 114.0(6) . . ?
C31 N4 C36 114.2(7) . . ?
C37 N4 C36 109.1(7) . . ?
C34 N5 C35 123.9(7) . . ?
C34 N5 C41 119.6(7) . . ?
C35 N5 C41 116.5(7) . . ?
C46 N6 C43 117.2(16) . . ?

_diffrn_measured_fraction_theta_max 0.841
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_[(3)2(I2F4)]
_database_code_depnum_ccdc_archive 'CCDC 1052882'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H42 F4 I2 N6 O4'
_chemical_formula_weight         1144.72

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'
I I -0.4742 1.8119 '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                   39.688(4)
_cell_length_b                   7.4100(7)
_cell_length_c                   31.521(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.019(8)
_cell_angle_gamma                90.00
_cell_volume                     9257.0(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2881
_cell_measurement_theta_min      2.8480
_cell_measurement_theta_max      22.8500

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4560
_exptl_absorpt_coefficient_mu    1.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'w scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29886
_diffrn_reflns_av_R_equivalents  0.1651
_diffrn_reflns_av_sigmaI/netI    0.2490
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         28.04
_reflns_number_total             9450
_reflns_number_gt                3468
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -44.00   43.00   1.0000  280.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2849   77.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega    7.00   45.00   1.0000  280.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2849   77.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   78.00   1.0000  280.0000
omega____ theta____ kappa____ phi______ frames
    -       15.3787   77.0000  150.0000 93

#__ type_ start__ end____ width___ exp.time_
  4 omega   20.00   69.00   1.0000  280.0000
omega____ theta____ kappa____ phi______ frames
    -       15.3787   77.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  5 omega   10.00   84.00   1.0000  280.0000
omega____ theta____ kappa____ phi______ frames
    -       15.3787   77.0000 -120.0000 74

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXs-97 (Sheldrick, 2005)'
_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 > 2σ(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)+(0.0152P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9450
_refine_ls_number_parameters     613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2590
_refine_ls_R_factor_gt           0.0882
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_refine_ls_shift/su_max          0.002
_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
C1 C 0.1689(2) -0.0029(12) 0.3715(3) 0.031(3) Uani 1 1 d . . .
C2 C 0.1968(2) 0.0284(12) 0.3482(3) 0.029(3) Uani 1 1 d . . .
C3 C 0.1960(2) 0.0019(12) 0.3050(4) 0.037(3) Uani 1 1 d . . .
H3 H 0.2149 0.0264 0.2898 0.044 Uiso 1 1 calc R . .
C4 C 0.1669(2) -0.0610(13) 0.2845(3) 0.038(3) Uani 1 1 d . . .
H4 H 0.1665 -0.0815 0.2554 0.046 Uiso 1 1 calc R . .
C5 C 0.1386(2) -0.0941(12) 0.3064(3) 0.036(3) Uani 1 1 d . . .
H5 H 0.1193 -0.1382 0.2919 0.043 Uiso 1 1 calc R . .
C6 C 0.1384(2) -0.0619(12) 0.3506(3) 0.031(3) Uani 1 1 d . . .
C7 C 0.1091(2) -0.0969(12) 0.3747(3) 0.032(3) Uani 1 1 d . . .
C8 C 0.1127(3) -0.0695(14) 0.4184(4) 0.053(3) Uani 1 1 d . . .
H8 H 0.0942 -0.0898 0.4347 0.064 Uiso 1 1 calc R . .
C9 C 0.1424(3) -0.0138(14) 0.4384(3) 0.047(3) Uani 1 1 d . . .
H9 H 0.1435 0.0006 0.4677 0.056 Uiso 1 1 calc R . .
C10 C 0.1705(2) 0.0215(12) 0.4162(3) 0.034(3) Uani 1 1 d . . .
C11 C 0.2014(3) 0.0924(13) 0.4387(4) 0.044(3) Uani 1 1 d . . .
C12 C 0.2282(3) 0.1005(14) 0.3696(4) 0.043(3) Uani 1 1 d . . .
C13 C 0.2581(2) 0.2150(14) 0.4341(4) 0.052(3) Uani 1 1 d . . .
H13A H 0.2510 0.2871 0.4578 0.063 Uiso 1 1 calc R . .
H13B H 0.2682 0.2960 0.4142 0.063 Uiso 1 1 calc R . .
C14 C 0.2842(2) 0.0839(13) 0.4503(3) 0.032(3) Uani 1 1 d . . .
C15 C 0.2784(2) -0.0844(14) 0.4662(3) 0.043(3) Uani 1 1 d . . .
H15 H 0.2563 -0.1268 0.4665 0.051 Uiso 1 1 calc R . .
C16 C 0.3040(3) -0.1908(14) 0.4816(3) 0.052(3) Uani 1 1 d . . .
H16 H 0.2997 -0.3059 0.4919 0.063 Uiso 1 1 calc R . .
C17 C 0.3364(3) -0.1247(17) 0.4818(3) 0.054(3) Uani 1 1 d . . .
H17 H 0.3539 -0.1968 0.4929 0.065 Uiso 1 1 calc R . .
C18 C 0.3180(3) 0.1363(15) 0.4518(3) 0.049(3) Uani 1 1 d . . .
H18 H 0.3230 0.2500 0.4414 0.059 Uiso 1 1 calc R . .
C19 C 0.0628(2) -0.0090(13) 0.3268(3) 0.037(3) Uani 1 1 d . . .
H19A H 0.0793 0.0501 0.3101 0.045 Uiso 1 1 calc R . .
H19B H 0.0529 0.0807 0.3449 0.045 Uiso 1 1 calc R . .
C20 C 0.0549(2) -0.2396(14) 0.3805(3) 0.047(3) Uani 1 1 d . . .
H20A H 0.0453 -0.1507 0.3990 0.057 Uiso 1 1 calc R . .
H20B H 0.0665 -0.3302 0.3981 0.057 Uiso 1 1 calc R . .
C21 C 0.0353(2) -0.0947(14) 0.2977(4) 0.053(3) Uani 1 1 d . . .
H21A H 0.0238 -0.0011 0.2811 0.064 Uiso 1 1 calc R . .
H21B H 0.0457 -0.1764 0.2782 0.064 Uiso 1 1 calc R . .
C22 C 0.0101(3) -0.1971(16) 0.3225(4) 0.062(4) Uani 1 1 d . . .
H22A H -0.0032 -0.1125 0.3382 0.074 Uiso 1 1 calc R . .
H22B H -0.0052 -0.2624 0.3030 0.074 Uiso 1 1 calc R . .
C23 C 0.0273(2) -0.3268(15) 0.3527(3) 0.051(3) Uani 1 1 d . . .
H23A H 0.0369 -0.4240 0.3366 0.061 Uiso 1 1 calc R . .
H23B H 0.0107 -0.3789 0.3706 0.061 Uiso 1 1 calc R . .
C24 C 0.8172(2) 0.5059(11) 0.6792(3) 0.027(2) Uani 1 1 d . . .
C25 C 0.7927(2) 0.4812(13) 0.7106(4) 0.039(3) Uani 1 1 d . . .
C26 C 0.8015(2) 0.5180(14) 0.7525(3) 0.042(3) Uani 1 1 d . . .
H26 H 0.7857 0.4992 0.7728 0.051 Uiso 1 1 calc R . .
C27 C 0.8329(3) 0.5820(13) 0.7651(3) 0.043(3) Uani 1 1 d . . .
H27 H 0.8378 0.6116 0.7934 0.052 Uiso 1 1 calc R . .
C28 C 0.8575(3) 0.6026(13) 0.7356(3) 0.037(3) Uani 1 1 d . . .
C29 C 0.8498(2) 0.5673(12) 0.6923(3) 0.026(2) Uani 1 1 d . . .
C30 C 0.8720(2) 0.5976(12) 0.6603(3) 0.033(3) Uani 1 1 d . . .
H30 H 0.8934 0.6416 0.6676 0.039 Uiso 1 1 calc R . .
C31 C 0.8635(3) 0.5657(14) 0.6194(4) 0.046(3) Uani 1 1 d . . .
H31 H 0.8791 0.5901 0.5992 0.055 Uiso 1 1 calc R . .
C32 C 0.8320(3) 0.4969(12) 0.6060(3) 0.041(3) Uani 1 1 d . . .
H32 H 0.8269 0.4728 0.5774 0.049 Uiso 1 1 calc R . .
C33 C 0.8082(3) 0.4649(13) 0.6364(4) 0.040(3) Uani 1 1 d . . .
C34 C 0.7751(3) 0.4014(13) 0.6231(4) 0.038(3) Uani 1 1 d . . .
C35 C 0.7597(3) 0.4055(14) 0.6982(4) 0.046(3) Uani 1 1 d . . .
C36 C 0.7194(2) 0.2895(13) 0.6434(3) 0.045(3) Uani 1 1 d . . .
H36A H 0.7149 0.1998 0.6648 0.053 Uiso 1 1 calc R . .
H36B H 0.7208 0.2278 0.6164 0.053 Uiso 1 1 calc R . .
C37 C 0.6906(2) 0.4236(14) 0.6403(3) 0.032(3) Uani 1 1 d . . .
C38 C 0.6889(3) 0.5845(15) 0.6582(4) 0.056(3) Uani 1 1 d . . .
H38 H 0.7074 0.6254 0.6748 0.067 Uiso 1 1 calc R . .
C39 C 0.6608(3) 0.6951(16) 0.6533(4) 0.065(4) Uani 1 1 d . . .
H39 H 0.6606 0.8105 0.6649 0.078 Uiso 1 1 calc R . .
C40 C 0.6331(3) 0.6275(18) 0.6306(4) 0.064(4) Uani 1 1 d . . .
H40 H 0.6136 0.6974 0.6282 0.077 Uiso 1 1 calc R . .
C41 C 0.6617(3) 0.3669(16) 0.6176(3) 0.052(3) Uani 1 1 d . . .
H41 H 0.6618 0.2526 0.6054 0.063 Uiso 1 1 calc R . .
C42 C 0.9160(2) 0.5165(14) 0.7473(3) 0.047(3) Uani 1 1 d . . .
H42A H 0.9128 0.4512 0.7207 0.056 Uiso 1 1 calc R . .
H42B H 0.9136 0.4320 0.7704 0.056 Uiso 1 1 calc R . .
C43 C 0.9509(3) 0.6001(15) 0.7505(4) 0.057(3) Uani 1 1 d . . .
H43A H 0.9678 0.5058 0.7498 0.068 Uiso 1 1 calc R . .
H43B H 0.9536 0.6793 0.7264 0.068 Uiso 1 1 calc R . .
C44 C 0.9558(3) 0.7058(17) 0.7911(4) 0.075(4) Uani 1 1 d . . .
H44A H 0.9562 0.6238 0.8151 0.090 Uiso 1 1 calc R . .
H44B H 0.9774 0.7678 0.7915 0.090 Uiso 1 1 calc R . .
C45 C 0.9283(3) 0.8401(16) 0.7951(3) 0.061(3) Uani 1 1 d . . .
H45A H 0.9309 0.8980 0.8227 0.073 Uiso 1 1 calc R . .
H45B H 0.9301 0.9324 0.7736 0.073 Uiso 1 1 calc R . .
C46 C 0.8945(3) 0.7544(15) 0.7904(3) 0.054(3) Uani 1 1 d . . .
H46A H 0.8919 0.6691 0.8133 0.065 Uiso 1 1 calc R . .
H46B H 0.8772 0.8461 0.7921 0.065 Uiso 1 1 calc R . .
C47 C 0.4654(3) 0.2164(15) 0.5586(4) 0.046(3) Uani 1 1 d . . .
C48 C 0.4963(3) 0.2596(15) 0.5741(4) 0.051(3) Uani 1 1 d . . .
C49 C 0.5232(2) 0.2866(14) 0.5477(4) 0.045(3) Uani 1 1 d . . .
C50 C 0.5166(3) 0.2709(15) 0.5057(4) 0.052(3) Uani 1 1 d . . .
C51 C 0.4841(3) 0.2290(16) 0.4895(4) 0.060(4) Uani 1 1 d . . .
C52 C 0.4587(3) 0.2044(13) 0.5162(4) 0.045(3) Uani 1 1 d . . .
N1 N 0.3437(2) 0.0352(14) 0.4671(3) 0.056(3) Uani 1 1 d . . .
N2 N 0.2278(2) 0.1309(11) 0.4128(3) 0.045(2) Uani 1 1 d . . .
N3 N 0.07894(19) -0.1521(11) 0.3530(2) 0.039(2) Uani 1 1 d . . .
N4 N 0.6329(2) 0.4669(14) 0.6119(3) 0.064(3) Uani 1 1 d . . .
N5 N 0.75198(18) 0.3779(10) 0.6546(3) 0.035(2) Uani 1 1 d . . .
N6 N 0.89043(19) 0.6600(10) 0.7492(3) 0.038(2) Uani 1 1 d . . .
O1 O 0.20346(18) 0.1152(11) 0.4767(2) 0.063(2) Uani 1 1 d . . .
O2 O 0.25390(17) 0.1278(10) 0.3513(2) 0.061(2) Uani 1 1 d . . .
O3 O 0.73827(17) 0.3733(11) 0.7234(2) 0.065(2) Uani 1 1 d . . .
O4 O 0.76643(17) 0.3647(10) 0.5865(2) 0.053(2) Uani 1 1 d . . .
F1 F 0.44124(15) 0.1963(9) 0.5859(2) 0.074(2) Uani 1 1 d . . .
F2 F 0.50247(14) 0.2736(9) 0.6170(2) 0.072(2) Uani 1 1 d . . .
F3 F 0.47941(16) 0.2129(10) 0.4476(2) 0.084(2) Uani 1 1 d . . .
F4 F 0.54045(16) 0.2969(10) 0.4780(2) 0.089(3) Uani 1 1 d . . .
I1 I 0.409129(17) 0.14063(11) 0.49187(3) 0.0566(3) Uani 1 1 d . . .
I2 I 0.571600(17) 0.35551(11) 0.57315(3) 0.0576(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C2 1.380(11) . ?
C1 C6 1.414(12) . ?
C1 C10 1.418(13) . ?
C2 C3 1.374(13) . ?
C2 C12 1.485(14) . ?
C3 C4 1.372(13) . ?
C4 C5 1.372(11) . ?
C5 C6 1.416(12) . ?
C6 C7 1.445(11) . ?
C7 C8 1.392(14) . ?
C7 N3 1.410(11) . ?
C8 C9 1.368(13) . ?
C9 C10 1.373(11) . ?
C10 C11 1.480(14) . ?
C11 O1 1.207(12) . ?
C11 N2 1.395(11) . ?
C12 O2 1.215(10) . ?
C12 N2 1.382(12) . ?
C13 N2 1.483(12) . ?
C13 C14 1.490(13) . ?
C14 C15 1.369(12) . ?
C14 C18 1.395(12) . ?
C15 C16 1.357(13) . ?
C16 C17 1.377(13) . ?
C17 N1 1.310(12) . ?
C18 N1 1.335(12) . ?
C19 N3 1.470(11) . ?
C19 C21 1.525(12) . ?
C20 N3 1.473(10) . ?
C20 C23 1.514(13) . ?
C21 C22 1.509(12) . ?
C22 C23 1.492(14) . ?
C24 C29 1.411(12) . ?
C24 C33 1.411(13) . ?
C24 C25 1.435(11) . ?
C25 C26 1.374(13) . ?
C25 C35 1.461(14) . ?
C26 C27 1.373(12) . ?
C27 C28 1.390(11) . ?
C28 C29 1.407(13) . ?
C28 N6 1.421(12) . ?
C29 C30 1.393(11) . ?
C30 C31 1.336(13) . ?
C31 C32 1.395(13) . ?
C32 C33 1.401(11) . ?
C33 C34 1.434(14) . ?
C34 O4 1.219(11) . ?
C34 N5 1.398(11) . ?
C35 O3 1.219(10) . ?
C35 N5 1.407(12) . ?
C36 N5 1.475(11) . ?
C36 C37 1.514(13) . ?
C37 C38 1.323(12) . ?
C37 C41 1.386(13) . ?
C38 C39 1.388(14) . ?
C39 C40 1.373(15) . ?
C40 N4 1.328(13) . ?
C41 N4 1.364(12) . ?
C42 N6 1.473(11) . ?
C42 C43 1.514(12) . ?
C43 C44 1.504(14) . ?
C44 C45 1.487(14) . ?
C45 C46 1.485(13) . ?
C46 N6 1.475(12) . ?
C47 F1 1.332(10) . ?
C47 C48 1.334(14) . ?
C47 C52 1.351(14) . ?
C48 F2 1.366(12) . ?
C48 C49 1.404(13) . ?
C49 C50 1.340(15) . ?
C49 I2 2.105(10) . ?
C50 F4 1.337(10) . ?
C50 C51 1.398(16) . ?
C51 F3 1.331(13) . ?
C51 C52 1.358(13) . ?
C52 I1 2.126(11) . ?

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
C2 C1 C6 119.6(9) . . ?
C2 C1 C10 120.7(9) . . ?
C6 C1 C10 119.7(9) . . ?
C3 C2 C1 121.7(10) . . ?
C3 C2 C12 118.4(9) . . ?
C1 C2 C12 119.8(9) . . ?
C4 C3 C2 119.3(9) . . ?
C3 C4 C5 121.0(10) . . ?
C4 C5 C6 120.7(9) . . ?
C1 C6 C5 117.6(9) . . ?
C1 C6 C7 120.1(9) . . ?
C5 C6 C7 122.3(9) . . ?
C8 C7 N3 124.3(9) . . ?
C8 C7 C6 116.8(9) . . ?
N3 C7 C6 118.9(9) . . ?
C9 C8 C7 122.6(10) . . ?
C8 C9 C10 121.8(10) . . ?
C9 C10 C1 119.0(10) . . ?
C9 C10 C11 119.8(10) . . ?
C1 C10 C11 121.1(9) . . ?
O1 C11 N2 122.6(11) . . ?
O1 C11 C10 122.5(10) . . ?
N2 C11 C10 114.9(10) . . ?
O2 C12 N2 119.5(10) . . ?
O2 C12 C2 123.5(10) . . ?
N2 C12 C2 117.0(9) . . ?
N2 C13 C14 114.4(8) . . ?
C15 C14 C18 115.0(10) . . ?
C15 C14 C13 126.2(9) . . ?
C18 C14 C13 118.7(9) . . ?
C16 C15 C14 121.5(10) . . ?
C15 C16 C17 118.5(10) . . ?
N1 C17 C16 123.0(10) . . ?
N1 C18 C14 124.9(11) . . ?
N3 C19 C21 108.3(8) . . ?
N3 C20 C23 108.6(8) . . ?
C22 C21 C19 111.7(9) . . ?
C23 C22 C21 111.1(9) . . ?
C22 C23 C20 112.8(9) . . ?
C29 C24 C33 122.1(9) . . ?
C29 C24 C25 118.8(9) . . ?
C33 C24 C25 119.1(9) . . ?
C26 C25 C24 119.5(9) . . ?
C26 C25 C35 120.8(10) . . ?
C24 C25 C35 119.6(10) . . ?
C27 C26 C25 121.8(10) . . ?
C26 C27 C28 120.1(10) . . ?
C27 C28 C29 120.3(10) . . ?
C27 C28 N6 119.7(9) . . ?
C29 C28 N6 120.0(8) . . ?
C30 C29 C28 124.0(9) . . ?
C30 C29 C24 116.4(9) . . ?
C28 C29 C24 119.5(9) . . ?
C31 C30 C29 122.2(10) . . ?
C30 C31 C32 122.2(9) . . ?
C31 C32 C33 118.8(10) . . ?
C32 C33 C24 118.0(10) . . ?
C32 C33 C34 119.7(10) . . ?
C24 C33 C34 122.1(9) . . ?
O4 C34 N5 118.7(10) . . ?
O4 C34 C33 123.9(10) . . ?
N5 C34 C33 117.3(10) . . ?
O3 C35 N5 119.1(10) . . ?
O3 C35 C25 123.2(11) . . ?
N5 C35 C25 117.6(9) . . ?
N5 C36 C37 111.9(8) . . ?
C38 C37 C41 115.8(11) . . ?
C38 C37 C36 128.2(10) . . ?
C41 C37 C36 115.9(10) . . ?
C37 C38 C39 122.9(11) . . ?
C40 C39 C38 117.4(11) . . ?
N4 C40 C39 123.0(12) . . ?
N4 C41 C37 124.6(11) . . ?
N6 C42 C43 109.3(8) . . ?
C44 C43 C42 110.4(9) . . ?
C45 C44 C43 111.0(10) . . ?
C46 C45 C44 111.7(10) . . ?
N6 C46 C45 110.4(8) . . ?
F1 C47 C48 117.9(11) . . ?
F1 C47 C52 121.4(11) . . ?
C48 C47 C52 120.6(10) . . ?
C47 C48 F2 119.7(10) . . ?
C47 C48 C49 121.9(11) . . ?
F2 C48 C49 118.3(10) . . ?
C50 C49 C48 117.2(10) . . ?
C50 C49 I2 121.7(9) . . ?
C48 C49 I2 121.1(8) . . ?
F4 C50 C49 121.6(11) . . ?
F4 C50 C51 117.8(11) . . ?
C49 C50 C51 120.6(11) . . ?
F3 C51 C52 122.3(12) . . ?
F3 C51 C50 117.4(11) . . ?
C52 C51 C50 120.3(11) . . ?
C47 C52 C51 119.2(11) . . ?
C47 C52 I1 120.2(8) . . ?
C51 C52 I1 120.6(9) . . ?
C17 N1 C18 117.2(10) . . ?
C12 N2 C11 126.3(9) . . ?
C12 N2 C13 117.8(9) . . ?
C11 N2 C13 115.9(9) . . ?
C7 N3 C19 113.5(8) . . ?
C7 N3 C20 113.6(8) . . ?
C19 N3 C20 111.8(7) . . ?
C40 N4 C41 116.3(10) . . ?
C34 N5 C35 123.9(9) . . ?
C34 N5 C36 119.1(9) . . ?
C35 N5 C36 116.1(8) . . ?
C28 N6 C46 117.7(8) . . ?
C28 N6 C42 113.3(8) . . ?
C46 N6 C42 109.6(8) . . ?

_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_4_1
_database_code_depnum_ccdc_archive 'CCDC 1052883'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O2'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43

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           orthorhombic
_symmetry_space_group_name_H-M   Pna21

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                   30.652(5)
_cell_length_b                   5.3082(9)
_cell_length_c                   11.243(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1829.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    932
_cell_measurement_theta_min      2.6527
_cell_measurement_theta_max      29.1866

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.42578
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7735
_diffrn_reflns_av_R_equivalents  0.1230
_diffrn_reflns_av_sigmaI/netI    0.1990
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         29.25
_reflns_number_total             3143
_reflns_number_gt                1171
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -83.00  -38.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4392  179.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega   67.00   94.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9236  179.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega   53.00   85.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9236   57.0000 -150.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -48.00   65.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -       18.9236    0.0000   30.0000 113

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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 > 2σ(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)+(0.0089P)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    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   2(3)
_refine_ls_number_reflns         3143
_refine_ls_number_parameters     253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2245
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0764
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.921
_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
C1 C -0.0179(2) 0.3909(11) 0.3302(6) 0.0419(18) Uani 1 1 d . . .
H1 H -0.0359 0.2910 0.3774 0.050 Uiso 1 1 calc R . .
C2 C 0.0269(2) 0.3569(10) 0.3349(6) 0.0430(18) Uani 1 1 d . . .
H2 H 0.0382 0.2349 0.3855 0.052 Uiso 1 1 calc R . .
C3 C 0.0551(2) 0.4982(12) 0.2668(6) 0.0392(18) Uani 1 1 d . . .
C4 C 0.0378(2) 0.6910(11) 0.1955(6) 0.0329(17) Uani 1 1 d . . .
C5 C -0.0079(2) 0.7337(10) 0.1905(6) 0.0357(17) Uani 1 1 d . . .
C6 C -0.0364(2) 0.5698(12) 0.2570(6) 0.0373(18) Uani 1 1 d . . .
C7 C -0.0231(2) 0.9426(10) 0.1244(6) 0.0388(17) Uani 1 1 d . . .
H7 H -0.0528 0.9796 0.1235 0.047 Uiso 1 1 calc R . .
C8 C 0.0052(3) 1.0905(10) 0.0619(6) 0.047(2) Uani 1 1 d . . .
H8 H -0.0056 1.2261 0.0186 0.056 Uiso 1 1 calc R . .
C9 C 0.0499(2) 1.0426(11) 0.0616(6) 0.048(2) Uani 1 1 d . . .
H9 H 0.0687 1.1435 0.0173 0.057 Uiso 1 1 calc R . .
C10 C 0.0661(2) 0.8447(11) 0.1272(6) 0.0377(18) Uani 1 1 d . . .
C11 C 0.1013(2) 0.4416(13) 0.2663(6) 0.045(2) Uani 1 1 d . . .
C12 C 0.1142(2) 0.7974(12) 0.1275(7) 0.0465(19) Uani 1 1 d . . .
C13 C 0.1741(2) 0.5191(13) 0.1884(7) 0.060(2) Uani 1 1 d . . .
H13A H 0.1874 0.6033 0.1210 0.072 Uiso 1 1 calc R . .
H13B H 0.1759 0.3390 0.1744 0.072 Uiso 1 1 calc R . .
C14 C 0.1999(2) 0.5822(12) 0.2995(6) 0.044(2) Uani 1 1 d . . .
C15 C 0.1916(2) 0.7881(12) 0.3708(7) 0.058(2) Uani 1 1 d . . .
H15 H 0.1685 0.8951 0.3527 0.070 Uiso 1 1 calc R . .
C16 C 0.2351(2) 0.4356(12) 0.3321(7) 0.054(2) Uani 1 1 d . . .
H16 H 0.2425 0.2951 0.2870 0.065 Uiso 1 1 calc R . .
C17 C 0.2592(2) 0.4965(14) 0.4311(8) 0.069(3) Uani 1 1 d . . .
H17 H 0.2828 0.3940 0.4505 0.083 Uiso 1 1 calc R . .
C18 C 0.2172(3) 0.8360(14) 0.4685(7) 0.060(2) Uani 1 1 d . . .
H18 H 0.2107 0.9760 0.5149 0.073 Uiso 1 1 calc R . .
C19 C -0.1091(2) 0.4833(12) 0.3397(7) 0.057(2) Uani 1 1 d . . .
H19A H -0.0957 0.5068 0.4170 0.069 Uiso 1 1 calc R . .
H19B H -0.1117 0.3038 0.3251 0.069 Uiso 1 1 calc R . .
C20 C -0.1541(2) 0.6033(14) 0.3388(7) 0.066(2) Uani 1 1 d . . .
H20A H -0.1722 0.5252 0.3993 0.079 Uiso 1 1 calc R . .
H20B H -0.1516 0.7811 0.3573 0.079 Uiso 1 1 calc R . .
C21 C -0.1756(2) 0.5714(14) 0.2171(7) 0.068(3) Uani 1 1 d . . .
H21A H -0.2033 0.6597 0.2159 0.082 Uiso 1 1 calc R . .
H21B H -0.1812 0.3943 0.2024 0.082 Uiso 1 1 calc R . .
C22 C -0.1459(2) 0.6758(12) 0.1203(7) 0.059(2) Uani 1 1 d . . .
H22A H -0.1585 0.6408 0.0428 0.071 Uiso 1 1 calc R . .
H22B H -0.1434 0.8570 0.1290 0.071 Uiso 1 1 calc R . .
C23 C -0.1011(2) 0.5559(11) 0.1291(6) 0.0458(19) Uani 1 1 d . . .
H23A H -0.1035 0.3763 0.1146 0.055 Uiso 1 1 calc R . .
H23B H -0.0822 0.6269 0.0685 0.055 Uiso 1 1 calc R . .
N1 N 0.2510(2) 0.6922(12) 0.5004(6) 0.0665(19) Uani 1 1 d . . .
N2 N 0.12850(18) 0.5918(10) 0.1952(5) 0.0445(15) Uani 1 1 d . . .
N3 N -0.08164(18) 0.5986(9) 0.2473(5) 0.0427(16) Uani 1 1 d . . .
O1 O 0.11748(15) 0.2703(8) 0.3249(4) 0.0581(14) Uani 1 1 d . . .
O2 O 0.13914(16) 0.9222(8) 0.0701(4) 0.0666(17) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.378(8) . ?
C1 C2 1.386(8) . ?
C2 C3 1.377(8) . ?
C3 C4 1.405(8) . ?
C3 C11 1.446(8) . ?
C4 C5 1.418(8) . ?
C4 C10 1.417(8) . ?
C5 C7 1.414(8) . ?
C5 C6 1.443(8) . ?
C6 N3 1.399(7) . ?
C7 C8 1.365(8) . ?
C8 C9 1.395(9) . ?
C9 C10 1.376(8) . ?
C10 C12 1.497(8) . ?
C11 O1 1.227(7) . ?
C11 N2 1.404(8) . ?
C12 O2 1.200(7) . ?
C12 N2 1.401(8) . ?
C13 N2 1.453(8) . ?
C13 C14 1.516(8) . ?
C14 C16 1.379(8) . ?
C14 C15 1.380(8) . ?
C15 C18 1.375(9) . ?
C16 C17 1.375(9) . ?
C17 N1 1.323(8) . ?
C18 N1 1.335(8) . ?
C19 N3 1.471(8) . ?
C19 C20 1.519(8) . ?
C20 C21 1.528(9) . ?
C21 C22 1.522(9) . ?
C22 C23 1.519(8) . ?
C23 N3 1.474(8) . ?

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
C6 C1 C2 121.3(6) . . ?
C3 C2 C1 122.0(6) . . ?
C2 C3 C4 118.4(6) . . ?
C2 C3 C11 120.2(6) . . ?
C4 C3 C11 121.3(6) . . ?
C3 C4 C5 120.8(6) . . ?
C3 C4 C10 119.8(6) . . ?
C5 C4 C10 119.4(6) . . ?
C7 C5 C4 118.2(6) . . ?
C7 C5 C6 123.0(6) . . ?
C4 C5 C6 118.8(6) . . ?
C1 C6 N3 122.0(6) . . ?
C1 C6 C5 118.4(6) . . ?
N3 C6 C5 119.6(6) . . ?
C8 C7 C5 120.7(6) . . ?
C7 C8 C9 121.4(6) . . ?
C10 C9 C8 119.4(7) . . ?
C9 C10 C4 120.7(6) . . ?
C9 C10 C12 119.0(6) . . ?
C4 C10 C12 120.4(6) . . ?
O1 C11 N2 119.1(7) . . ?
O1 C11 C3 123.2(7) . . ?
N2 C11 C3 117.8(6) . . ?
O2 C12 N2 121.6(7) . . ?
O2 C12 C10 122.3(7) . . ?
N2 C12 C10 116.1(6) . . ?
N2 C13 C14 113.6(6) . . ?
C16 C14 C15 116.0(7) . . ?
C16 C14 C13 120.1(7) . . ?
C15 C14 C13 123.9(7) . . ?
C18 C15 C14 120.3(7) . . ?
C17 C16 C14 120.2(7) . . ?
N1 C17 C16 124.0(7) . . ?
N1 C18 C15 123.5(8) . . ?
N3 C19 C20 109.9(6) . . ?
C21 C20 C19 110.5(7) . . ?
C20 C21 C22 110.1(6) . . ?
C23 C22 C21 110.0(6) . . ?
N3 C23 C22 111.1(6) . . ?
C17 N1 C18 116.0(7) . . ?
C12 N2 C11 124.5(6) . . ?
C12 N2 C13 118.6(6) . . ?
C11 N2 C13 116.8(6) . . ?
C6 N3 C23 117.0(6) . . ?
C6 N3 C19 117.8(6) . . ?
C23 N3 C19 110.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.227
_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/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_4_2
_database_code_depnum_ccdc_archive 'CCDC 1052884'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O2'
_chemical_formula_sum            'C23 H21 N3 O2'
_chemical_formula_weight         371.43

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   P21/a

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

_cell_length_a                   7.4142(19)
_cell_length_b                   16.069(4)
_cell_length_c                   15.802(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.08(3)
_cell_angle_gamma                90.00
_cell_volume                     1879.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    513
_cell_measurement_theta_min      2.7457
_cell_measurement_theta_max      29.3978

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8601
_diffrn_reflns_av_R_equivalents  0.0911
_diffrn_reflns_av_sigmaI/netI    0.2298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         29.46
_reflns_number_total             4343
_reflns_number_gt                1546
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   38.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580  179.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
  2 omega  -26.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580    0.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   81.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       19.1580   38.0000    0.0000 77

;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'Sir-92    (altomare, giacovazzo, 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 > 2σ(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)+(0.0080P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0012(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4343
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2948
_refine_ls_R_factor_gt           0.1117
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
C1 C 0.0572(6) 0.0350(3) -0.1870(3) 0.0426(14) Uani 1 1 d . . .
H1 H 0.0083 -0.0106 -0.2163 0.051 Uiso 1 1 calc R . .
C2 C 0.1322(6) 0.0233(3) -0.1056(3) 0.0400(14) Uani 1 1 d . . .
H2 H 0.1308 -0.0292 -0.0810 0.048 Uiso 1 1 calc R . .
C3 C 0.2082(6) 0.0889(3) -0.0614(3) 0.0302(12) Uani 1 1 d . . .
C4 C 0.1971(5) 0.1695(3) -0.0956(3) 0.0267(12) Uani 1 1 d . . .
C5 C 0.1134(5) 0.1824(3) -0.1773(3) 0.0293(12) Uani 1 1 d . . .
C6 C 0.0525(6) 0.1118(3) -0.2263(3) 0.0350(13) Uani 1 1 d . . .
C7 C 0.0848(6) 0.2652(3) -0.2045(3) 0.0377(13) Uani 1 1 d . . .
H7 H 0.0254 0.2751 -0.2569 0.045 Uiso 1 1 calc R . .
C8 C 0.1426(6) 0.3314(3) -0.1555(3) 0.0366(13) Uani 1 1 d . . .
H8 H 0.1202 0.3854 -0.1742 0.044 Uiso 1 1 calc R . .
C9 C 0.2351(5) 0.3176(3) -0.0776(3) 0.0325(12) Uani 1 1 d . . .
H9 H 0.2796 0.3625 -0.0457 0.039 Uiso 1 1 calc R . .
C10 C 0.2607(6) 0.2382(3) -0.0478(3) 0.0279(12) Uani 1 1 d . . .
C11 C 0.3022(6) 0.0746(3) 0.0216(3) 0.0377(13) Uani 1 1 d . . .
C12 C 0.3611(6) 0.2265(3) 0.0351(3) 0.0319(12) Uani 1 1 d . . .
C13 C 0.5023(6) 0.1288(3) 0.1372(3) 0.0453(14) Uani 1 1 d . . .
H13A H 0.6009 0.1685 0.1375 0.054 Uiso 1 1 calc R . .
H13B H 0.5540 0.0736 0.1326 0.054 Uiso 1 1 calc R . .
C14 C 0.4142(7) 0.1349(3) 0.2200(3) 0.0373(13) Uani 1 1 d . . .
C15 C 0.2423(7) 0.1628(3) 0.2296(3) 0.0482(15) Uani 1 1 d . . .
H15 H 0.1694 0.1778 0.1823 0.058 Uiso 1 1 calc R . .
C16 C 0.5143(8) 0.1144(4) 0.2932(4) 0.076(2) Uani 1 1 d . . .
H16 H 0.6323 0.0955 0.2903 0.092 Uiso 1 1 calc R . .
C17 C 0.4396(10) 0.1221(5) 0.3696(4) 0.099(3) Uani 1 1 d . . .
H17 H 0.5095 0.1066 0.4177 0.119 Uiso 1 1 calc R . .
C18 C 0.1771(8) 0.1689(3) 0.3098(4) 0.0697(19) Uani 1 1 d . . .
H18 H 0.0591 0.1872 0.3145 0.084 Uiso 1 1 calc R . .
C19 C -0.1306(6) 0.0592(3) -0.3478(3) 0.0557(16) Uani 1 1 d . . .
H19A H -0.2142 0.0388 -0.3074 0.067 Uiso 1 1 calc R . .
H19B H -0.0543 0.0131 -0.3632 0.067 Uiso 1 1 calc R . .
C20 C -0.2359(7) 0.0915(3) -0.4267(3) 0.0655(18) Uani 1 1 d . . .
H20A H -0.3210 0.1336 -0.4104 0.079 Uiso 1 1 calc R . .
H20B H -0.3039 0.0462 -0.4535 0.079 Uiso 1 1 calc R . .
C21 C -0.1088(8) 0.1286(3) -0.4896(3) 0.0724(19) Uani 1 1 d . . .
H21A H -0.0367 0.0846 -0.5128 0.087 Uiso 1 1 calc R . .
H21B H -0.1791 0.1544 -0.5360 0.087 Uiso 1 1 calc R . .
C22 C 0.0148(7) 0.1929(3) -0.4468(3) 0.0588(16) Uani 1 1 d . . .
H22A H 0.1027 0.2114 -0.4859 0.071 Uiso 1 1 calc R . .
H22B H -0.0556 0.2407 -0.4309 0.071 Uiso 1 1 calc R . .
C23 C 0.1118(6) 0.1561(3) -0.3683(3) 0.0510(15) Uani 1 1 d . . .
H23A H 0.1890 0.1108 -0.3848 0.061 Uiso 1 1 calc R . .
H23B H 0.1876 0.1983 -0.3406 0.061 Uiso 1 1 calc R . .
N1 N 0.2734(8) 0.1501(4) 0.3804(3) 0.0855(19) Uani 1 1 d . . .
N2 N 0.3826(5) 0.1441(2) 0.0618(2) 0.0312(10) Uani 1 1 d . . .
N3 N -0.0192(5) 0.1250(2) -0.3088(2) 0.0415(11) Uani 1 1 d . . .
O1 O 0.3141(5) 0.00678(18) 0.0558(2) 0.0590(11) Uani 1 1 d . . .
O2 O 0.4238(4) 0.28242(18) 0.0780(2) 0.0436(10) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.381(5) . ?
C1 C2 1.386(5) . ?
C2 C3 1.369(5) . ?
C3 C4 1.405(5) . ?
C3 C11 1.470(6) . ?
C4 C10 1.404(5) . ?
C4 C5 1.417(5) . ?
C5 C7 1.411(5) . ?
C5 C6 1.434(5) . ?
C6 N3 1.397(5) . ?
C7 C8 1.371(5) . ?
C8 C9 1.394(5) . ?
C9 C10 1.370(5) . ?
C10 C12 1.484(5) . ?
C11 O1 1.218(5) . ?
C11 N2 1.401(5) . ?
C12 O2 1.204(5) . ?
C12 N2 1.396(5) . ?
C13 N2 1.468(5) . ?
C13 C14 1.497(6) . ?
C14 C15 1.368(6) . ?
C14 C16 1.380(6) . ?
C15 C18 1.384(6) . ?
C16 C17 1.360(7) . ?
C17 N1 1.332(7) . ?
C18 N1 1.326(6) . ?
C19 N3 1.458(5) . ?
C19 C20 1.526(5) . ?
C20 C21 1.527(6) . ?
C21 C22 1.516(6) . ?
C22 C23 1.518(5) . ?
C23 N3 1.475(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.5(4) . . ?
C3 C2 C1 120.2(4) . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 C11 119.9(4) . . ?
C4 C3 C11 120.1(4) . . ?
C10 C4 C3 120.5(4) . . ?
C10 C4 C5 119.5(4) . . ?
C3 C4 C5 119.9(4) . . ?
C7 C5 C4 117.8(4) . . ?
C7 C5 C6 122.9(4) . . ?
C4 C5 C6 119.1(4) . . ?
C1 C6 N3 123.7(4) . . ?
C1 C6 C5 117.7(4) . . ?
N3 C6 C5 118.5(4) . . ?
C8 C7 C5 121.4(4) . . ?
C7 C8 C9 120.0(4) . . ?
C10 C9 C8 120.2(4) . . ?
C9 C10 C4 120.8(4) . . ?
C9 C10 C12 118.3(4) . . ?
C4 C10 C12 120.9(4) . . ?
O1 C11 N2 119.5(4) . . ?
O1 C11 C3 123.7(5) . . ?
N2 C11 C3 116.8(4) . . ?
O2 C12 N2 120.3(5) . . ?
O2 C12 C10 124.3(4) . . ?
N2 C12 C10 115.5(4) . . ?
N2 C13 C14 115.2(4) . . ?
C15 C14 C16 116.6(5) . . ?
C15 C14 C13 124.9(4) . . ?
C16 C14 C13 118.5(5) . . ?
C14 C15 C18 119.9(5) . . ?
C17 C16 C14 119.8(6) . . ?
N1 C17 C16 124.5(6) . . ?
N1 C18 C15 123.7(6) . . ?
N3 C19 C20 110.6(4) . . ?
C19 C20 C21 111.0(4) . . ?
C22 C21 C20 110.8(4) . . ?
C23 C22 C21 110.3(4) . . ?
N3 C23 C22 110.6(4) . . ?
C18 N1 C17 115.5(6) . . ?
C12 N2 C11 125.4(4) . . ?
C12 N2 C13 117.3(4) . . ?
C11 N2 C13 117.3(4) . . ?
C6 N3 C19 117.5(4) . . ?
C6 N3 C23 114.6(4) . . ?
C19 N3 C23 110.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.831
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_[(4)2(I2F4)]
_database_code_depnum_ccdc_archive 'CCDC 1052885'
_audit_update_record             
;
2015-03-09 deposited with the CCDC.
2015-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N3 O2, 0.5(C6 F4 I2)'
_chemical_formula_sum            'C26 H21 F2 I N3 O2'
_chemical_formula_weight         572.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   12.989(5)
_cell_length_b                   13.783(5)
_cell_length_c                   12.664(5)
_cell_angle_alpha                90.000
_cell_angle_beta                 92.047(5)
_cell_angle_gamma                90.000
_cell_volume                     2265.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2775
_cell_measurement_theta_min      3.1290
_cell_measurement_theta_max      25.9220

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.678
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1140
_exptl_absorpt_coefficient_mu    1.460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10219
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         29.36
_reflns_number_total             5206
_reflns_number_gt                3656
_reflns_threshold_expression     >2σ(I)
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   24.00   49.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -      -17.8298   77.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   -9.00   70.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   79.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000   90.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega   -8.00   20.00   1.0000    1.2000
omega____ theta____ kappa____ phi______ frames
    -       19.0017   77.0000  -30.0000 28

;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SIR 92 (Altomare, Giacovazzo, 1994)'
_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 > 2σ(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)+(0.0193P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5206
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C -0.0831(3) 0.0480(3) 0.1995(3) 0.0608(11) Uani 1 1 d . . .
H1 H -0.1357 0.0752 0.1574 0.073 Uiso 1 1 calc R . .
C2 C -0.0271(3) -0.0259(3) 0.1572(3) 0.0509(9) Uani 1 1 d . . .
H2 H -0.0419 -0.0472 0.0887 0.061 Uiso 1 1 calc R . .
C3 C 0.0510(2) -0.0683(3) 0.2169(3) 0.0470(9) Uani 1 1 d . . .
C4 C 0.0698(3) -0.0319(3) 0.3171(3) 0.0613(11) Uani 1 1 d . . .
H4 H 0.1227 -0.0571 0.3603 0.074 Uiso 1 1 calc R . .
C5 C 0.0085(3) 0.0426(3) 0.3522(3) 0.0616(11) Uani 1 1 d . . .
H5 H 0.0219 0.0657 0.4203 0.074 Uiso 1 1 calc R . .
C6 C 0.1108(2) -0.1531(3) 0.1749(3) 0.0565(10) Uani 1 1 d . . .
H6A H 0.0798 -0.2129 0.1987 0.068 Uiso 1 1 calc R . .
H6B H 0.1055 -0.1523 0.0984 0.068 Uiso 1 1 calc R . .
C7 C 0.2858(3) -0.0947(3) 0.1510(3) 0.0489(9) Uani 1 1 d . . .
C8 C 0.3963(2) -0.0981(2) 0.1830(3) 0.0388(8) Uani 1 1 d . . .
C9 C 0.4635(3) -0.0377(3) 0.1334(3) 0.0493(9) Uani 1 1 d . . .
H9 H 0.4387 0.0046 0.0812 0.059 Uiso 1 1 calc R . .
C10 C 0.5687(3) -0.0392(3) 0.1605(3) 0.0500(9) Uani 1 1 d . . .
H10 H 0.6134 0.0030 0.1276 0.060 Uiso 1 1 calc R . .
C11 C 0.6060(2) -0.1030(2) 0.2358(2) 0.0403(8) Uani 1 1 d . . .
H11 H 0.6762 -0.1040 0.2528 0.048 Uiso 1 1 calc R . .
C12 C 0.5398(2) -0.1672(2) 0.2881(2) 0.0361(7) Uani 1 1 d . . .
C13 C 0.5756(2) -0.2319(2) 0.3701(3) 0.0387(8) Uani 1 1 d . . .
C14 C 0.5039(3) -0.2787(2) 0.4299(3) 0.0460(9) Uani 1 1 d . . .
H14 H 0.5260 -0.3161 0.4874 0.055 Uiso 1 1 calc R . .
C15 C 0.3981(3) -0.2705(2) 0.4049(3) 0.0457(9) Uani 1 1 d . . .
H15 H 0.3513 -0.3038 0.4453 0.055 Uiso 1 1 calc R . .
C16 C 0.3625(2) -0.2144(2) 0.3223(3) 0.0380(8) Uani 1 1 d . . .
C17 C 0.4326(2) -0.1611(2) 0.2630(2) 0.0351(7) Uani 1 1 d . . .
C18 C 0.7435(2) -0.2815(3) 0.3054(2) 0.0492(9) Uani 1 1 d . . .
H18A H 0.7173 -0.2578 0.2374 0.059 Uiso 1 1 calc R . .
H18B H 0.7382 -0.3517 0.3055 0.059 Uiso 1 1 calc R . .
C19 C 0.8551(3) -0.2514(3) 0.3229(3) 0.0667(12) Uani 1 1 d . . .
H19A H 0.8960 -0.2788 0.2676 0.080 Uiso 1 1 calc R . .
H19B H 0.8603 -0.1813 0.3190 0.080 Uiso 1 1 calc R . .
C20 C 0.8966(3) -0.2855(3) 0.4287(3) 0.0754(13) Uani 1 1 d . . .
H20A H 0.9660 -0.2610 0.4410 0.090 Uiso 1 1 calc R . .
H20B H 0.8995 -0.3558 0.4296 0.090 Uiso 1 1 calc R . .
C21 C 0.8284(3) -0.2502(3) 0.5153(3) 0.0656(12) Uani 1 1 d . . .
H21A H 0.8333 -0.1801 0.5205 0.079 Uiso 1 1 calc R . .
H21B H 0.8524 -0.2775 0.5824 0.079 Uiso 1 1 calc R . .
C22 C 0.7167(3) -0.2789(3) 0.4937(3) 0.0527(10) Uani 1 1 d . . .
H22A H 0.7104 -0.3491 0.4938 0.063 Uiso 1 1 calc R . .
H22B H 0.6742 -0.2532 0.5486 0.063 Uiso 1 1 calc R . .
C23 C 0.4091(2) 0.0249(2) 0.4512(3) 0.0398(8) Uani 1 1 d . . .
C24 C 0.4068(2) -0.0388(2) 0.5340(3) 0.0381(8) Uani 1 1 d . . .
C25 C 0.5003(3) -0.0636(2) 0.5825(3) 0.0401(8) Uani 1 1 d . . .
C26 C 0.2506(3) -0.2084(2) 0.2976(3) 0.0473(9) Uani 1 1 d . . .
N1 N 0.2206(2) -0.1523(2) 0.2088(2) 0.0475(7) Uani 1 1 d . . .
N2 N 0.6820(2) -0.2404(2) 0.3910(2) 0.0419(7) Uani 1 1 d . . .
N3 N -0.0677(2) 0.0837(2) 0.2961(3) 0.0587(9) Uani 1 1 d . . .
O1 O 0.25171(19) -0.0458(2) 0.0773(2) 0.0675(8) Uani 1 1 d . . .
O2 O 0.18606(19) -0.24831(18) 0.3495(2) 0.0660(7) Uani 1 1 d . . .
F1 F 0.32048(14) 0.05151(15) 0.39942(16) 0.0602(6) Uani 1 1 d . . .
F2 F 0.50375(15) -0.12665(15) 0.66339(16) 0.0614(6) Uani 1 1 d . . .
I1 I 0.267327(17) -0.086803(17) 0.592317(18) 0.05051(10) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 N3 1.327(5) . ?
C1 C2 1.372(5) . ?
C2 C3 1.374(4) . ?
C3 C4 1.378(5) . ?
C3 C6 1.510(4) . ?
C4 C5 1.383(5) . ?
C5 N3 1.324(5) . ?
C6 N1 1.475(4) . ?
C7 O1 1.222(4) . ?
C7 N1 1.389(4) . ?
C7 C8 1.478(5) . ?
C8 C9 1.374(4) . ?
C8 C17 1.403(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.372(4) . ?
C11 C12 1.416(4) . ?
C12 C17 1.419(4) . ?
C12 C13 1.433(4) . ?
C13 C14 1.380(4) . ?
C13 N2 1.403(4) . ?
C14 C15 1.404(4) . ?
C15 C16 1.368(4) . ?
C16 C17 1.408(4) . ?
C16 C26 1.478(4) . ?
C18 N2 1.481(4) . ?
C18 C19 1.516(4) . ?
C19 C20 1.502(5) . ?
C20 C21 1.515(5) . ?
C21 C22 1.520(5) . ?
C22 N2 1.462(4) . ?
C23 F1 1.355(3) . ?
C23 C24 1.368(4) . ?
C23 C25 1.374(4) 3_656 ?
C24 C25 1.384(4) . ?
C24 I1 2.089(3) . ?
C25 F2 1.342(3) . ?
C25 C23 1.374(4) 3_656 ?
C26 O2 1.215(4) . ?
C26 N1 1.407(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
N3 C1 C2 124.8(4) . . ?
C1 C2 C3 119.5(4) . . ?
C2 C3 C4 117.0(3) . . ?
C2 C3 C6 121.0(3) . . ?
C4 C3 C6 122.0(3) . . ?
C3 C4 C5 118.8(4) . . ?
N3 C5 C4 124.9(4) . . ?
N1 C6 C3 113.4(3) . . ?
O1 C7 N1 120.5(3) . . ?
O1 C7 C8 123.3(3) . . ?
N1 C7 C8 116.2(3) . . ?
C9 C8 C17 120.1(3) . . ?
C9 C8 C7 118.8(3) . . ?
C17 C8 C7 121.0(3) . . ?
C8 C9 C10 120.7(3) . . ?
C11 C10 C9 119.9(3) . . ?
C10 C11 C12 121.4(3) . . ?
C11 C12 C17 117.7(3) . . ?
C11 C12 C13 122.8(3) . . ?
C17 C12 C13 119.3(3) . . ?
C14 C13 N2 122.4(3) . . ?
C14 C13 C12 118.7(3) . . ?
N2 C13 C12 118.7(3) . . ?
C13 C14 C15 120.8(3) . . ?
C16 C15 C14 121.4(3) . . ?
C15 C16 C17 119.6(3) . . ?
C15 C16 C26 119.8(3) . . ?
C17 C16 C26 120.5(3) . . ?
C8 C17 C16 120.1(3) . . ?
C8 C17 C12 120.0(3) . . ?
C16 C17 C12 119.8(3) . . ?
N2 C18 C19 109.0(3) . . ?
C20 C19 C18 110.8(3) . . ?
C19 C20 C21 110.1(3) . . ?
C20 C21 C22 111.4(3) . . ?
N2 C22 C21 109.2(3) . . ?
F1 C23 C24 120.2(3) . . ?
F1 C23 C25 117.8(3) . 3_656 ?
C24 C23 C25 122.0(3) . 3_656 ?
C23 C24 C25 117.1(3) . . ?
C23 C24 I1 121.1(2) . . ?
C25 C24 I1 121.5(2) . . ?
F2 C25 C23 118.9(3) . 3_656 ?
F2 C25 C24 120.2(3) . . ?
C23 C25 C24 120.9(3) 3_656 . ?
O2 C26 N1 120.3(3) . . ?
O2 C26 C16 123.5(4) . . ?
N1 C26 C16 116.2(3) . . ?
C7 N1 C26 125.4(3) . . ?
C7 N1 C6 116.9(3) . . ?
C26 N1 C6 117.7(3) . . ?
C13 N2 C22 118.0(3) . . ?
C13 N2 C18 116.6(3) . . ?
C22 N2 C18 110.8(3) . . ?
C5 N3 C1 114.9(3) . . ?

_diffrn_measured_fraction_theta_max 0.836
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.074


