# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_is_sm407
_audit_block_doi                 10.5517/ccy4yzz
_database_code_depnum_ccdc_archive 'CCDC 868712'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1055/s-0032-1316826 2013
_audit_update_record             
;
2012-02-22 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H10 O4'
_chemical_formula_sum            'C16 H10 O4'
_chemical_formula_weight         266.24

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60

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

_cell_length_a                   10.7720(6)
_cell_length_b                   12.0538(7)
_cell_length_c                   18.4416(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2394.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4759
_cell_measurement_theta_min      5.532
_cell_measurement_theta_max      60.427

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9605
_exptl_absorpt_correction_T_max  0.9936
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20244
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_sigmaI/netI    0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3178
_reflns_number_gt                2547
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA

_refine_special_details          
;
All H atoms (except H3) were positioned geometrically and refined using a
riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups),
1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) =
1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times
Ueq(C) (methylene groups, aryl CH, methine groups). Torsion angles
of all methyl groups were allowed to refine.

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)+(0.0438P)²+1.1519P] 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         3178
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0446
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80074(9) 0.13989(8) 0.40690(5) 0.0223(2) Uani 1 1 d . . .
O2 O 0.97131(10) 0.43855(8) 0.36909(5) 0.0277(2) Uani 1 1 d . . .
O3 O 0.92944(10) 0.39577(9) 0.54947(6) 0.0283(2) Uani 1 1 d . . .
O4 O 1.06456(10) 0.24510(9) 0.55254(6) 0.0270(2) Uani 1 1 d . . .
C1 C 0.87859(13) 0.18578(11) 0.45585(7) 0.0201(3) Uani 1 1 d . . .
C2 C 0.93760(13) 0.28381(11) 0.44613(7) 0.0199(3) Uani 1 1 d . . .
C3 C 0.92362(13) 0.34597(11) 0.37975(7) 0.0215(3) Uani 1 1 d . . .
C4 C 0.84621(13) 0.29172(11) 0.32466(7) 0.0210(3) Uani 1 1 d . . .
C5 C 0.82810(14) 0.33733(12) 0.25514(7) 0.0247(3) Uani 1 1 d . . .
H5 H 0.8711 0.4029 0.2416 0.030 Uiso 1 1 calc R . .
C6 C 0.74857(15) 0.28745(13) 0.20690(8) 0.0283(3) Uani 1 1 d . . .
H6 H 0.7375 0.3182 0.1599 0.034 Uiso 1 1 calc R . .
C7 C 0.68363(15) 0.19137(13) 0.22675(8) 0.0291(3) Uani 1 1 d . . .
H7 H 0.6268 0.1589 0.1936 0.035 Uiso 1 1 calc R . .
C8 C 0.70129(14) 0.14350(13) 0.29382(8) 0.0262(3) Uani 1 1 d . . .
H8 H 0.6579 0.0780 0.3072 0.031 Uiso 1 1 calc R . .
C9 C 0.78449(13) 0.19354(11) 0.34166(7) 0.0211(3) Uani 1 1 d . . .
C10 C 1.01038(13) 0.33084(12) 0.50848(8) 0.0227(3) Uani 1 1 d . . .
H10 H 1.0781 0.3791 0.4890 0.027 Uiso 1 1 calc R . .
C12 C 0.99235(13) 0.15436(12) 0.56756(8) 0.0229(3) Uani 1 1 d . . .
C13 C 1.02100(15) 0.09251(13) 0.62917(8) 0.0282(3) Uani 1 1 d . . .
H13 H 1.0853 0.1157 0.6610 0.034 Uiso 1 1 calc R . .
C14 C 0.95448(15) -0.00317(13) 0.64321(8) 0.0308(3) Uani 1 1 d . . .
H14 H 0.9737 -0.0457 0.6851 0.037 Uiso 1 1 calc R . .
C15 C 0.85976(15) -0.03859(13) 0.59714(8) 0.0282(3) Uani 1 1 d . . .
H15 H 0.8148 -0.1045 0.6077 0.034 Uiso 1 1 calc R . .
C16 C 0.83175(14) 0.02270(12) 0.53612(8) 0.0251(3) Uani 1 1 d . . .
H16 H 0.7678 -0.0014 0.5043 0.030 Uiso 1 1 calc R . .
C17 C 0.89703(13) 0.12013(12) 0.52088(7) 0.0212(3) Uani 1 1 d . . .
H3 H 0.973(2) 0.454(2) 0.5734(14) 0.076(8) Uiso 1 1 d . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
O1 C1 1.3505(16) . ?
O1 C9 1.3772(16) . ?
O2 C3 1.2441(17) . ?
O3 C10 1.3942(18) . ?
O3 H3 0.95(3) . ?
O4 C12 1.3704(17) . ?
O4 C10 1.4384(17) . ?
C1 C2 1.3537(19) . ?
C1 C17 1.4506(19) . ?
C2 C3 1.4431(19) . ?
C2 C10 1.5027(19) . ?
C3 C4 1.4681(19) . ?
C4 C9 1.393(2) . ?
C4 C5 1.4085(19) . ?
C5 C6 1.374(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.402(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C10 H10 1.0000 . ?
C12 C13 1.3937(19) . ?
C12 C17 1.402(2) . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.395(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.397(2) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 118.07(11) . . ?
C10 O3 H3 111.1(16) . . ?
C12 O4 C10 117.21(11) . . ?
O1 C1 C2 124.10(12) . . ?
O1 C1 C17 114.47(12) . . ?
C2 C1 C17 121.42(13) . . ?
C1 C2 C3 121.10(12) . . ?
C1 C2 C10 118.23(12) . . ?
C3 C2 C10 120.51(12) . . ?
O2 C3 C2 123.83(13) . . ?
O2 C3 C4 121.64(13) . . ?
C2 C3 C4 114.52(12) . . ?
C9 C4 C5 118.05(13) . . ?
C9 C4 C3 119.59(12) . . ?
C5 C4 C3 122.33(13) . . ?
C6 C5 C4 120.33(14) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.25(14) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.76(14) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 118.39(14) . . ?
C7 C8 H8 120.8 . . ?
C9 C8 H8 120.8 . . ?
O1 C9 C4 122.34(12) . . ?
O1 C9 C8 115.54(13) . . ?
C4 C9 C8 122.12(13) . . ?
O3 C10 O4 110.54(12) . . ?
O3 C10 C2 107.48(12) . . ?
O4 C10 C2 111.89(11) . . ?
O3 C10 H10 109.0 . . ?
O4 C10 H10 109.0 . . ?
C2 C10 H10 109.0 . . ?
O4 C12 C13 117.78(13) . . ?
O4 C12 C17 121.78(12) . . ?
C13 C12 C17 120.35(14) . . ?
C14 C13 C12 118.96(14) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 121.38(14) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 H14 119.3 . . ?
C16 C15 C14 119.54(14) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.26(14) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 119.50(13) . . ?
C16 C17 C1 123.77(13) . . ?
C12 C17 C1 116.57(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 C2 3.02(19) . . . . ?
C9 O1 C1 C17 -175.90(11) . . . . ?
O1 C1 C2 C3 -2.0(2) . . . . ?
C17 C1 C2 C3 176.87(12) . . . . ?
O1 C1 C2 C10 173.36(12) . . . . ?
C17 C1 C2 C10 -7.8(2) . . . . ?
C1 C2 C3 O2 176.83(14) . . . . ?
C10 C2 C3 O2 1.6(2) . . . . ?
C1 C2 C3 C4 -2.49(19) . . . . ?
C10 C2 C3 C4 -177.72(12) . . . . ?
O2 C3 C4 C9 -173.48(13) . . . . ?
C2 C3 C4 C9 5.85(19) . . . . ?
O2 C3 C4 C5 4.3(2) . . . . ?
C2 C3 C4 C5 -176.36(13) . . . . ?
C9 C4 C5 C6 2.0(2) . . . . ?
C3 C4 C5 C6 -175.80(13) . . . . ?
C4 C5 C6 C7 0.7(2) . . . . ?
C5 C6 C7 C8 -2.1(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C1 O1 C9 C4 0.70(19) . . . . ?
C1 O1 C9 C8 -178.82(12) . . . . ?
C5 C4 C9 O1 176.91(12) . . . . ?
C3 C4 C9 O1 -5.2(2) . . . . ?
C5 C4 C9 C8 -3.6(2) . . . . ?
C3 C4 C9 C8 174.29(13) . . . . ?
C7 C8 C9 O1 -178.15(13) . . . . ?
C7 C8 C9 C4 2.3(2) . . . . ?
C12 O4 C10 O3 77.74(14) . . . . ?
C12 O4 C10 C2 -42.02(17) . . . . ?
C1 C2 C10 O3 -88.80(15) . . . . ?
C3 C2 C10 O3 86.56(15) . . . . ?
C1 C2 C10 O4 32.73(18) . . . . ?
C3 C2 C10 O4 -151.91(12) . . . . ?
C10 O4 C12 C13 -156.53(13) . . . . ?
C10 O4 C12 C17 27.06(19) . . . . ?
O4 C12 C13 C14 -176.13(13) . . . . ?
C17 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C17 -0.6(2) . . . . ?
C15 C16 C17 C12 0.9(2) . . . . ?
C15 C16 C17 C1 176.19(13) . . . . ?
O4 C12 C17 C16 175.59(13) . . . . ?
C13 C12 C17 C16 -0.7(2) . . . . ?
O4 C12 C17 C1 -0.1(2) . . . . ?
C13 C12 C17 C1 -176.40(13) . . . . ?
O1 C1 C17 C16 -6.0(2) . . . . ?
C2 C1 C17 C16 175.08(14) . . . . ?
O1 C1 C17 C12 169.49(12) . . . . ?
C2 C1 C17 C12 -9.5(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_ah_sm805
_database_code_depnum_ccdc_archive 'CCDC 1016268'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H26 Br F N2 O2'
_chemical_formula_sum            'C32 H26 Br F N2 O2'
_chemical_formula_weight         569.46

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

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                   12.1385(4)
_cell_length_b                   10.7741(3)
_cell_length_c                   20.8967(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.598(2)
_cell_angle_gamma                90.00
_cell_volume                     2724.10(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      29.98

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1168
_exptl_absorpt_coefficient_mu    1.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5000
_exptl_absorpt_correction_T_max  0.6983
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            76363
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.13
_diffrn_reflns_theta_max         31.13
_reflns_number_total             8727
_reflns_number_gt                6496
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine. The geometry of the disordered 
 parts was constrained to be equal (SAME 0.01) and the Uij of C25A/C25B, 
 C26A/C26B, C27A/C27B, C28A/C28B, C29A/C29B, C30A/C30B, C31A/C31B, and 
 C32A/C32B were set to be identical (EADP).
 
 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)+(0.0358P)²+0.9371P] 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         8727
_refine_ls_number_parameters     372
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0798
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.251132(15) 0.126800(19) 0.018217(7) 0.04479(6) Uani 1 1 d . . .
F1 F 0.69894(7) -0.26588(9) -0.17165(5) 0.0456(2) Uani 1 1 d . A .
O1 O -0.06460(8) 0.06653(11) -0.21714(6) 0.0354(2) Uani 1 1 d . . .
H1 H -0.024(2) 0.061(3) -0.2501(13) 0.083(8) Uiso 1 1 d . . .
O2 O 0.29948(8) -0.14857(9) -0.18380(5) 0.0299(2) Uani 1 1 d . . .
N1 N 0.09892(9) 0.05103(10) -0.28384(6) 0.0248(2) Uani 1 1 d . . .
N2 N 0.45844(9) 0.13424(10) -0.26973(6) 0.0228(2) Uani 1 1 d . . .
C1 C 0.15318(12) 0.10755(13) -0.05691(7) 0.0302(3) Uani 1 1 d . . .
C2 C 0.03970(13) 0.11455(15) -0.05172(8) 0.0373(3) Uani 1 1 d . . .
H2 H 0.0117 0.1289 -0.0112 0.045 Uiso 1 1 calc R . .
C3 C -0.03143(12) 0.10046(15) -0.10586(8) 0.0368(3) Uani 1 1 d . . .
H3 H -0.1089 0.1047 -0.1024 0.044 Uiso 1 1 calc R . .
C4 C 0.00844(11) 0.07997(13) -0.16580(7) 0.0276(3) Uani 1 1 d . . .
C5 C 0.12393(10) 0.07398(12) -0.17103(7) 0.0222(2) Uani 1 1 d . . .
C6 C 0.19510(11) 0.08865(12) -0.11535(7) 0.0252(3) Uani 1 1 d . . .
H6 H 0.2728 0.0855 -0.1180 0.030 Uiso 1 1 calc R . .
C7 C 0.16855(10) 0.05603(11) -0.23410(6) 0.0207(2) Uani 1 1 d . A .
C8 C 0.29096(9) 0.04511(11) -0.23691(6) 0.0198(2) Uani 1 1 d . . .
C9 C 0.34802(10) 0.13665(11) -0.26477(6) 0.0219(2) Uani 1 1 d . A .
H9 H 0.3078 0.2065 -0.2818 0.026 Uiso 1 1 calc R . .
C10 C 0.51989(10) 0.03275(12) -0.24655(6) 0.0220(2) Uani 1 1 d . A .
C11 C 0.63530(10) 0.02665(13) -0.25058(7) 0.0289(3) Uani 1 1 d . . .
H11 H 0.6723 0.0918 -0.2708 0.035 Uiso 1 1 calc R A .
C12 C 0.69431(11) -0.07325(14) -0.22532(8) 0.0325(3) Uani 1 1 d . A .
H12 H 0.7720 -0.0774 -0.2277 0.039 Uiso 1 1 calc R . .
C13 C 0.63908(11) -0.16775(14) -0.19637(8) 0.0317(3) Uani 1 1 d . . .
C14 C 0.52775(11) -0.16533(13) -0.19117(7) 0.0275(3) Uani 1 1 d . A .
H14 H 0.4924 -0.2312 -0.1706 0.033 Uiso 1 1 calc R . .
C15 C 0.46651(10) -0.06437(11) -0.21668(6) 0.0214(2) Uani 1 1 d . . .
C16 C 0.34675(9) -0.06271(11) -0.21045(6) 0.0205(2) Uani 1 1 d . A .
C17 C 0.13531(11) 0.03980(15) -0.34879(7) 0.0313(3) Uani 1 1 d . . .
H17A H 0.1864 -0.0315 -0.3506 0.038 Uiso 1 1 calc R . .
H17B H 0.1757 0.1158 -0.3596 0.038 Uiso 1 1 calc R . .
C18 C 0.03574(12) 0.02102(14) -0.39768(7) 0.0319(3) Uani 1 1 d . . .
H18A H -0.0192 0.0869 -0.3914 0.038 Uiso 1 1 calc R . .
H18B H 0.0604 0.0307 -0.4414 0.038 Uiso 1 1 calc R . .
C19 C -0.01961(12) -0.10342(14) -0.39316(7) 0.0294(3) Uani 1 1 d . . .
C20 C -0.11679(13) -0.11698(15) -0.36338(7) 0.0346(3) Uani 1 1 d . . .
H20 H -0.1489 -0.0469 -0.3445 0.042 Uiso 1 1 calc R . .
C21 C -0.16789(15) -0.23239(18) -0.36078(8) 0.0448(4) Uani 1 1 d . . .
H21 H -0.2341 -0.2408 -0.3398 0.054 Uiso 1 1 calc R . .
C22 C -0.12265(17) -0.33422(17) -0.38847(9) 0.0489(5) Uani 1 1 d . . .
H22 H -0.1581 -0.4127 -0.3873 0.059 Uiso 1 1 calc R . .
C23 C -0.02564(17) -0.32208(16) -0.41796(10) 0.0490(4) Uani 1 1 d . . .
H23 H 0.0061 -0.3924 -0.4368 0.059 Uiso 1 1 calc R . .
C24 C 0.02554(14) -0.20771(16) -0.42018(9) 0.0411(4) Uani 1 1 d . . .
H24 H 0.0925 -0.2003 -0.4405 0.049 Uiso 1 1 calc R . .
C25A C 0.5075(5) 0.2377(7) -0.3029(2) 0.0307(6) Uani 0.867(7) 1 d PD A 1
H25A H 0.5750 0.2651 -0.2771 0.037 Uiso 0.867(7) 1 calc PR A 1
H25B H 0.4548 0.3080 -0.3052 0.037 Uiso 0.867(7) 1 calc PR A 1
C26A C 0.5379(3) 0.2081(4) -0.3711(2) 0.0380(6) Uani 0.867(7) 1 d PD A 1
H26A H 0.5582 0.2861 -0.3922 0.046 Uiso 0.867(7) 1 calc PR A 1
H26B H 0.6036 0.1533 -0.3684 0.046 Uiso 0.867(7) 1 calc PR A 1
C27A C 0.4458(4) 0.1460(3) -0.4118(3) 0.0331(5) Uani 0.867(7) 1 d PD A 1
C28A C 0.4476(3) 0.0180(3) -0.42134(19) 0.0421(6) Uani 0.867(7) 1 d PD A 1
H28A H 0.5062 -0.0298 -0.4011 0.051 Uiso 0.867(7) 1 calc PR A 1
C29A C 0.3649(2) -0.0405(3) -0.45991(14) 0.0501(6) Uani 0.867(7) 1 d PD A 1
H29A H 0.3670 -0.1278 -0.4661 0.060 Uiso 0.867(7) 1 calc PR A 1
C30A C 0.27958(19) 0.0289(4) -0.48922(11) 0.0482(8) Uani 0.867(7) 1 d PD A 1
H30A H 0.2238 -0.0107 -0.5165 0.058 Uiso 0.867(7) 1 calc PR A 1
C31A C 0.27468(18) 0.1548(4) -0.47930(12) 0.0450(8) Uani 0.867(7) 1 d PD A 1
H31A H 0.2150 0.2019 -0.4990 0.054 Uiso 0.867(7) 1 calc PR A 1
C32A C 0.35751(19) 0.2130(3) -0.44031(13) 0.0393(6) Uani 0.867(7) 1 d PD A 1
H32A H 0.3535 0.2999 -0.4331 0.047 Uiso 0.867(7) 1 calc PR A 1
C25B C 0.520(4) 0.247(5) -0.2965(17) 0.0307(6) Uani 0.133(7) 1 d PD A 2
H25D H 0.4708 0.3210 -0.3007 0.037 Uiso 0.133(7) 1 calc PR A 2
H25E H 0.5866 0.2685 -0.2685 0.037 Uiso 0.133(7) 1 calc PR A 2
C26B C 0.550(2) 0.202(3) -0.3624(16) 0.0380(6) Uani 0.133(7) 1 d PD A 2
H26D H 0.5907 0.2684 -0.3830 0.046 Uiso 0.133(7) 1 calc PR A 2
H26E H 0.5998 0.1294 -0.3562 0.046 Uiso 0.133(7) 1 calc PR A 2
C27B C 0.451(2) 0.165(2) -0.4066(19) 0.0331(5) Uani 0.133(7) 1 d PD A 2
C28B C 0.4403(19) 0.0447(18) -0.4294(15) 0.0421(6) Uani 0.133(7) 1 d PD A 2
H28B H 0.4979 -0.0132 -0.4186 0.051 Uiso 0.133(7) 1 calc PR A 2
C29B C 0.3474(17) 0.0058(18) -0.4676(10) 0.0501(6) Uani 0.133(7) 1 d PD A 2
H29B H 0.3350 -0.0793 -0.4778 0.060 Uiso 0.133(7) 1 calc PR A 2
C30B C 0.2745(14) 0.096(2) -0.4900(9) 0.0482(8) Uani 0.133(7) 1 d PD A 2
H30B H 0.2176 0.0755 -0.5221 0.058 Uiso 0.133(7) 1 calc PR A 2
C31B C 0.2813(12) 0.215(2) -0.4677(8) 0.0450(8) Uani 0.133(7) 1 d PD A 2
H31B H 0.2243 0.2728 -0.4800 0.054 Uiso 0.133(7) 1 calc PR A 2
C32B C 0.3712(14) 0.2521(16) -0.4272(9) 0.0393(6) Uani 0.133(7) 1 d PD A 2
H32B H 0.3782 0.3360 -0.4136 0.047 Uiso 0.133(7) 1 calc PR A 2


#==============================================================================

# MOLECULAR GEOMETRY

_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
Br1 C1 1.9031(15) . ?
F1 C13 1.3610(16) . ?
O1 C4 1.3437(18) . ?
O1 H1 0.88(3) . ?
O2 C16 1.2435(15) . ?
N1 C7 1.2871(17) . ?
N1 C17 1.4655(19) . ?
N2 C9 1.3528(16) . ?
N2 C10 1.3887(17) . ?
N2 C25A 1.465(7) . ?
N2 C25B 1.55(5) . ?
C1 C6 1.375(2) . ?
C1 C2 1.392(2) . ?
C2 C3 1.375(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.4164(17) . ?
C5 C6 1.4014(19) . ?
C5 C7 1.4772(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4963(16) . ?
C8 C9 1.3624(17) . ?
C8 C16 1.4331(17) . ?
C9 H9 0.9500 . ?
C10 C15 1.4032(18) . ?
C10 C11 1.4117(17) . ?
C11 C12 1.375(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3646(19) . ?
C14 C15 1.3987(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.4700(16) . ?
C17 C18 1.5322(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.506(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.385(2) . ?
C19 C24 1.390(2) . ?
C20 C21 1.393(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.375(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25A C26A 1.533(3) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C26A C27A 1.507(3) . ?
C26A H26A 0.9900 . ?
C26A H26B 0.9900 . ?
C27A C32A 1.387(3) . ?
C27A C28A 1.393(3) . ?
C28A C29A 1.387(3) . ?
C28A H28A 0.9500 . ?
C29A C30A 1.380(4) . ?
C29A H29A 0.9500 . ?
C30A C31A 1.375(4) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.392(3) . ?
C31A H31A 0.9500 . ?
C32A H32A 0.9500 . ?
C25B C26B 1.534(9) . ?
C25B H25D 0.9900 . ?
C25B H25E 0.9900 . ?
C26B C27B 1.503(8) . ?
C26B H26D 0.9900 . ?
C26B H26E 0.9900 . ?
C27B C28B 1.387(9) . ?
C27B C32B 1.392(8) . ?
C28B C29B 1.394(9) . ?
C28B H28B 0.9500 . ?
C29B C30B 1.373(10) . ?
C29B H29B 0.9500 . ?
C30B C31B 1.363(10) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.385(9) . ?
C31B H31B 0.9500 . ?
C32B H32B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 H1 105.1(17) . . ?
C7 N1 C17 121.61(11) . . ?
C9 N2 C10 119.74(10) . . ?
C9 N2 C25A 117.7(3) . . ?
C10 N2 C25A 122.5(3) . . ?
C9 N2 C25B 121(2) . . ?
C10 N2 C25B 119(2) . . ?
C25A N2 C25B 7.5(14) . . ?
C6 C1 C2 121.05(14) . . ?
C6 C1 Br1 119.83(11) . . ?
C2 C1 Br1 119.11(12) . . ?
C3 C2 C1 119.32(14) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.03(13) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
O1 C4 C3 118.65(12) . . ?
O1 C4 C5 121.82(13) . . ?
C3 C4 C5 119.53(13) . . ?
C6 C5 C4 118.61(12) . . ?
C6 C5 C7 120.65(11) . . ?
C4 C5 C7 120.72(12) . . ?
C1 C6 C5 120.44(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C5 117.52(11) . . ?
N1 C7 C8 123.70(12) . . ?
C5 C7 C8 118.78(11) . . ?
C9 C8 C16 120.73(11) . . ?
C9 C8 C7 120.02(11) . . ?
C16 C8 C7 119.25(11) . . ?
N2 C9 C8 124.03(11) . . ?
N2 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
N2 C10 C15 119.21(11) . . ?
N2 C10 C11 121.58(12) . . ?
C15 C10 C11 119.18(12) . . ?
C12 C11 C10 120.18(13) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 119.20(12) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
F1 C13 C14 119.12(14) . . ?
F1 C13 C12 118.33(12) . . ?
C14 C13 C12 122.54(13) . . ?
C13 C14 C15 118.95(13) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C14 C15 C10 119.94(11) . . ?
C14 C15 C16 118.35(11) . . ?
C10 C15 C16 121.70(11) . . ?
O2 C16 C8 123.71(11) . . ?
O2 C16 C15 121.72(11) . . ?
C8 C16 C15 114.57(11) . . ?
N1 C17 C18 110.37(11) . . ?
N1 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C19 C18 C17 114.07(12) . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C24 118.37(14) . . ?
C20 C19 C18 121.50(14) . . ?
C24 C19 C18 120.12(14) . . ?
C19 C20 C21 120.65(16) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 120.12(17) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C23 119.78(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.13(17) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.94(17) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
N2 C25A C26A 114.8(4) . . ?
N2 C25A H25A 108.6 . . ?
C26A C25A H25A 108.6 . . ?
N2 C25A H25B 108.6 . . ?
C26A C25A H25B 108.6 . . ?
H25A C25A H25B 107.6 . . ?
C27A C26A C25A 113.2(2) . . ?
C27A C26A H26A 108.9 . . ?
C25A C26A H26A 108.9 . . ?
C27A C26A H26B 108.9 . . ?
C25A C26A H26B 108.9 . . ?
H26A C26A H26B 107.7 . . ?
C32A C27A C28A 118.32(19) . . ?
C32A C27A C26A 121.6(2) . . ?
C28A C27A C26A 120.1(2) . . ?
C29A C28A C27A 120.9(2) . . ?
C29A C28A H28A 119.5 . . ?
C27A C28A H28A 119.5 . . ?
C30A C29A C28A 119.6(2) . . ?
C30A C29A H29A 120.2 . . ?
C28A C29A H29A 120.2 . . ?
C31A C30A C29A 120.5(2) . . ?
C31A C30A H30A 119.8 . . ?
C29A C30A H30A 119.8 . . ?
C30A C31A C32A 119.7(2) . . ?
C30A C31A H31A 120.2 . . ?
C32A C31A H31A 120.2 . . ?
C27A C32A C31A 120.9(2) . . ?
C27A C32A H32A 119.5 . . ?
C31A C32A H32A 119.5 . . ?
C26B C25B N2 103(3) . . ?
C26B C25B H25D 111.1 . . ?
N2 C25B H25D 111.1 . . ?
C26B C25B H25E 111.1 . . ?
N2 C25B H25E 111.1 . . ?
H25D C25B H25E 109.1 . . ?
C27B C26B C25B 113.6(13) . . ?
C27B C26B H26D 108.8 . . ?
C25B C26B H26D 108.8 . . ?
C27B C26B H26E 108.8 . . ?
C25B C26B H26E 108.9 . . ?
H26D C26B H26E 107.7 . . ?
C28B C27B C32B 118.5(9) . . ?
C28B C27B C26B 120.4(11) . . ?
C32B C27B C26B 121.0(12) . . ?
C27B C28B C29B 122.0(11) . . ?
C27B C28B H28B 119.0 . . ?
C29B C28B H28B 119.0 . . ?
C30B C29B C28B 116.8(10) . . ?
C30B C29B H29B 121.6 . . ?
C28B C29B H29B 121.6 . . ?
C31B C30B C29B 122.1(11) . . ?
C31B C30B H30B 118.9 . . ?
C29B C30B H30B 118.9 . . ?
C30B C31B C32B 120.1(10) . . ?
C30B C31B H31B 119.9 . . ?
C32B C31B H31B 119.9 . . ?
C31B C32B C27B 119.5(10) . . ?
C31B C32B H32B 120.2 . . ?
C27B C32B H32B 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(2) . . . . ?
Br1 C1 C2 C3 -179.88(12) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 O1 179.84(14) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
O1 C4 C5 C6 -179.90(13) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
O1 C4 C5 C7 1.7(2) . . . . ?
C3 C4 C5 C7 -178.22(13) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
Br1 C1 C6 C5 179.82(10) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C7 C5 C6 C1 178.84(12) . . . . ?
C17 N1 C7 C5 176.85(12) . . . . ?
C17 N1 C7 C8 -2.9(2) . . . . ?
C6 C5 C7 N1 -175.69(12) . . . . ?
C4 C5 C7 N1 2.66(18) . . . . ?
C6 C5 C7 C8 4.12(18) . . . . ?
C4 C5 C7 C8 -177.54(11) . . . . ?
N1 C7 C8 C9 68.07(17) . . . . ?
C5 C7 C8 C9 -111.72(14) . . . . ?
N1 C7 C8 C16 -111.49(15) . . . . ?
C5 C7 C8 C16 68.71(15) . . . . ?
C10 N2 C9 C8 1.2(2) . . . . ?
C25A N2 C9 C8 178.0(2) . . . . ?
C25B N2 C9 C8 -174.3(12) . . . . ?
C16 C8 C9 N2 -0.1(2) . . . . ?
C7 C8 C9 N2 -179.64(12) . . . . ?
C9 N2 C10 C15 -1.74(19) . . . . ?
C25A N2 C10 C15 -178.4(2) . . . . ?
C25B N2 C10 C15 173.9(12) . . . . ?
C9 N2 C10 C11 -179.80(12) . . . . ?
C25A N2 C10 C11 3.6(3) . . . . ?
C25B N2 C10 C11 -4.2(13) . . . . ?
N2 C10 C11 C12 177.89(13) . . . . ?
C15 C10 C11 C12 -0.2(2) . . . . ?
C10 C11 C12 C13 0.4(2) . . . . ?
C11 C12 C13 F1 180.00(13) . . . . ?
C11 C12 C13 C14 -0.7(2) . . . . ?
F1 C13 C14 C15 -179.95(13) . . . . ?
C12 C13 C14 C15 0.8(2) . . . . ?
C13 C14 C15 C10 -0.5(2) . . . . ?
C13 C14 C15 C16 -179.71(13) . . . . ?
N2 C10 C15 C14 -177.88(12) . . . . ?
C11 C10 C15 C14 0.2(2) . . . . ?
N2 C10 C15 C16 1.28(19) . . . . ?
C11 C10 C15 C16 179.38(12) . . . . ?
C9 C8 C16 O2 179.14(13) . . . . ?
C7 C8 C16 O2 -1.3(2) . . . . ?
C9 C8 C16 C15 -0.39(18) . . . . ?
C7 C8 C16 C15 179.18(11) . . . . ?
C14 C15 C16 O2 -0.6(2) . . . . ?
C10 C15 C16 O2 -179.76(13) . . . . ?
C14 C15 C16 C8 178.95(12) . . . . ?
C10 C15 C16 C8 -0.22(18) . . . . ?
C7 N1 C17 C18 173.55(12) . . . . ?
N1 C17 C18 C19 -69.79(17) . . . . ?
C17 C18 C19 C20 101.56(16) . . . . ?
C17 C18 C19 C24 -79.59(18) . . . . ?
C24 C19 C20 C21 -0.1(2) . . . . ?
C18 C19 C20 C21 178.74(14) . . . . ?
C19 C20 C21 C22 -0.6(2) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
C20 C19 C24 C23 0.6(2) . . . . ?
C18 C19 C24 C23 -178.31(15) . . . . ?
C9 N2 C25A C26A -104.0(4) . . . . ?
C10 N2 C25A C26A 72.7(4) . . . . ?
C25B N2 C25A C26A 137(18) . . . . ?
N2 C25A C26A C27A 49.1(6) . . . . ?
C25A C26A C27A C32A 78.8(7) . . . . ?
C25A C26A C27A C28A -100.8(6) . . . . ?
C32A C27A C28A C29A 2.0(8) . . . . ?
C26A C27A C28A C29A -178.5(4) . . . . ?
C27A C28A C29A C30A -0.1(6) . . . . ?
C28A C29A C30A C31A -1.5(4) . . . . ?
C29A C30A C31A C32A 1.2(3) . . . . ?
C28A C27A C32A C31A -2.3(8) . . . . ?
C26A C27A C32A C31A 178.2(3) . . . . ?
C30A C31A C32A C27A 0.8(5) . . . . ?
C9 N2 C25B C26B -109(3) . . . . ?
C10 N2 C25B C26B 76(3) . . . . ?
C25A N2 C25B C26B -44(15) . . . . ?
N2 C25B C26B C27B 59(4) . . . . ?
C25B C26B C27B C28B -119(5) . . . . ?
C25B C26B C27B C32B 63(5) . . . . ?
C32B C27B C28B C29B -6(6) . . . . ?
C26B C27B C28B C29B 176(3) . . . . ?
C27B C28B C29B C30B 10(5) . . . . ?
C28B C29B C30B C31B -11(4) . . . . ?
C29B C30B C31B C32B 8(4) . . . . ?
C30B C31B C32B C27B -4(4) . . . . ?
C28B C27B C32B C31B 2(6) . . . . ?
C26B C27B C32B C31B -180(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        31.13
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.050
####################################################################### 
# 
# 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_ah_sm817_2
_database_code_depnum_ccdc_archive 'CCDC 1016269'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H27 F N2 O2'
_chemical_formula_sum            'C32 H27 F N2 O2'
_chemical_formula_weight         490.55

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5336(3)
_cell_length_b                   9.2212(4)
_cell_length_c                   16.6852(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.580(2)
_cell_angle_gamma                90
_cell_volume                     1281.44(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5455
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      30.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             516
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6871
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18967
_diffrn_reflns_av_unetI/netI     0.0447
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.209
_diffrn_reflns_theta_max         30.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.809
_diffrn_reflns_point_group_measured_fraction_full 0.914
_reflns_number_total             6620
_reflns_number_gt                5144
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.629
_reflns_Friedel_fraction_max     0.626
_reflns_Friedel_fraction_full    0.828

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms (except H1) were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups).
 
 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     
'w=1/[σ²(Fo²)+(0.0367P)²+0.1098P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1816 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6620
_refine_ls_number_parameters     338
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.64327(16) 0.10190(16) 1.21197(8) 0.0463(4) Uani 1 1 d . . . . .
O1 O 0.90483(16) 0.38836(19) 0.92486(10) 0.0407(4) Uani 1 1 d . . . . .
O2 O 0.72896(18) 0.7320(2) 0.68834(9) 0.0376(4) Uani 1 1 d . . . . .
H1 H 0.703(4) 0.630(4) 0.691(2) 0.083(11) Uiso 1 1 d . . . . .
N2 N 0.65943(18) 0.49068(19) 0.74333(10) 0.0274(4) Uani 1 1 d . . . . .
N1 N 0.45127(18) 0.37394(19) 0.96827(10) 0.0259(4) Uani 1 1 d . . . . .
C1 C 0.5740(2) 0.3033(2) 1.02281(12) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.5449(2) 0.2320(2) 1.09236(13) 0.0283(5) Uani 1 1 d . . . . .
H2B H 0.4404 0.2297 1.1035 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6716(3) 0.1661(2) 1.14373(14) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.8271(3) 0.1626(3) 1.13074(14) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.9111 0.1139 1.1676 0.042 Uiso 1 1 calc R U . . .
C5 C 0.8542(2) 0.2327(2) 1.06240(14) 0.0313(5) Uani 1 1 d . . . . .
H5 H 0.9592 0.2320 1.0518 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7306(2) 0.3054(2) 1.00779(12) 0.0255(4) Uani 1 1 d . . . . .
C7 C 0.7675(2) 0.3844(2) 0.93806(12) 0.0274(5) Uani 1 1 d . . . . .
C8 C 0.6327(2) 0.4568(2) 0.88638(12) 0.0251(4) Uani 1 1 d . . . . .
C9 C 0.4837(2) 0.4475(2) 0.90383(12) 0.0269(4) Uani 1 1 d . . . . .
H9 H 0.3974 0.4959 0.8683 0.032 Uiso 1 1 calc R U . . .
C10 C 0.6602(2) 0.5447(2) 0.81490(13) 0.0264(4) Uani 1 1 d . . . . .
C11 C 0.6965(2) 0.7003(3) 0.82730(13) 0.0300(5) Uani 1 1 d . . . . .
C12 C 0.7032(3) 0.7667(3) 0.90379(15) 0.0444(6) Uani 1 1 d . . . . .
H12 H 0.6797 0.7110 0.9477 0.053 Uiso 1 1 calc R U . . .
C13 C 0.7433(4) 0.9114(3) 0.91641(18) 0.0551(7) Uani 1 1 d . . . . .
H13 H 0.7477 0.9541 0.9687 0.066 Uiso 1 1 calc R U . . .
C14 C 0.7766(3) 0.9934(3) 0.85347(18) 0.0507(7) Uani 1 1 d . . . . .
H14 H 0.8041 1.0928 0.8626 0.061 Uiso 1 1 calc R U . . .
C15 C 0.7706(3) 0.9332(3) 0.77729(17) 0.0415(6) Uani 1 1 d . . . . .
H15 H 0.7931 0.9912 0.7341 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7316(2) 0.7874(3) 0.76344(14) 0.0316(5) Uani 1 1 d . . . . .
C17 C 0.6347(2) 0.3378(2) 0.72444(14) 0.0303(5) Uani 1 1 d . . . . .
H17A H 0.6322 0.2839 0.7754 0.036 Uiso 1 1 calc R U . . .
H17B H 0.7258 0.3003 0.7025 0.036 Uiso 1 1 calc R U . . .
C18 C 0.4777(2) 0.3114(3) 0.66138(14) 0.0341(5) Uani 1 1 d . . . . .
H18A H 0.4712 0.3794 0.6149 0.041 Uiso 1 1 calc R U . . .
H18B H 0.4777 0.2115 0.6397 0.041 Uiso 1 1 calc R U . . .
C19 C 0.3326(2) 0.3315(2) 0.69789(12) 0.0290(5) Uani 1 1 d . . . . .
C20 C 0.2754(3) 0.2174(3) 0.73748(14) 0.0362(5) Uani 1 1 d . . . . .
H20 H 0.3256 0.1252 0.7393 0.043 Uiso 1 1 calc R U . . .
C21 C 0.1465(3) 0.2357(3) 0.77444(15) 0.0414(6) Uani 1 1 d . . . . .
H21 H 0.1083 0.1561 0.8009 0.050 Uiso 1 1 calc R U . . .
C22 C 0.0735(2) 0.3692(3) 0.77289(14) 0.0396(6) Uani 1 1 d . . . . .
H22 H -0.0147 0.3819 0.7984 0.047 Uiso 1 1 calc R U . . .
C23 C 0.1290(3) 0.4843(3) 0.73414(14) 0.0387(5) Uani 1 1 d . . . . .
H23 H 0.0791 0.5766 0.7332 0.046 Uiso 1 1 calc R U . . .
C24 C 0.2576(2) 0.4654(3) 0.69654(13) 0.0337(5) Uani 1 1 d . . . . .
H24 H 0.2947 0.5449 0.6696 0.040 Uiso 1 1 calc R U . . .
C25 C 0.2854(2) 0.3757(3) 0.98210(13) 0.0284(5) Uani 1 1 d . . . . .
H25A H 0.2610 0.2798 1.0030 0.034 Uiso 1 1 calc R U . . .
H25B H 0.2091 0.3923 0.9290 0.034 Uiso 1 1 calc R U . . .
C26 C 0.2604(2) 0.4925(2) 1.04289(13) 0.0309(5) Uani 1 1 d . . . . .
H26A H 0.1520 0.4810 1.0543 0.037 Uiso 1 1 calc R U . . .
H26B H 0.3398 0.4781 1.0952 0.037 Uiso 1 1 calc R U . . .
C27 C 0.2769(2) 0.6443(3) 1.01263(13) 0.0319(5) Uani 1 1 d . . . . .
C28 C 0.1656(3) 0.6992(3) 0.94590(16) 0.0458(6) Uani 1 1 d . . . . .
H28 H 0.0769 0.6413 0.9200 0.055 Uiso 1 1 calc R U . . .
C29 C 0.1833(4) 0.8372(3) 0.91717(19) 0.0603(8) Uani 1 1 d . . . . .
H29 H 0.1076 0.8730 0.8710 0.072 Uiso 1 1 calc R U . . .
C30 C 0.3099(4) 0.9234(3) 0.9548(2) 0.0634(8) Uani 1 1 d . . . . .
H30 H 0.3213 1.0185 0.9350 0.076 Uiso 1 1 calc R U . . .
C31 C 0.4201(4) 0.8704(3) 1.02167(19) 0.0580(8) Uani 1 1 d . . . . .
H31 H 0.5074 0.9294 1.0481 0.070 Uiso 1 1 calc R U . . .
C32 C 0.4035(3) 0.7319(3) 1.05019(15) 0.0442(6) Uani 1 1 d . . . . .
H32 H 0.4799 0.6962 1.0961 0.053 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C3 1.351(3) . ?
O1 C7 1.240(2) . ?
O2 C16 1.349(3) . ?
O2 H1 0.97(4) . ?
N2 C10 1.293(3) . ?
N2 C17 1.450(3) . ?
N1 C9 1.350(3) . ?
N1 C1 1.391(2) . ?
N1 C25 1.483(2) . ?
C1 C2 1.402(3) . ?
C1 C6 1.413(2) . ?
C2 C3 1.367(3) . ?
C2 H2B 0.9500 . ?
C3 C4 1.391(3) . ?
C4 C5 1.373(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.464(3) . ?
C7 C8 1.443(3) . ?
C8 C9 1.367(3) . ?
C8 C10 1.502(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.473(3) . ?
C11 C12 1.405(3) . ?
C11 C16 1.418(3) . ?
C12 C13 1.382(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.373(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(3) . ?
C15 H15 0.9500 . ?
C17 C18 1.532(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.505(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.386(3) . ?
C19 C24 1.389(3) . ?
C20 C21 1.384(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(3) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.525(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.505(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.385(3) . ?
C27 C28 1.392(3) . ?
C28 C29 1.379(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 O2 H1 106(2) . . ?
C10 N2 C17 123.14(18) . . ?
C9 N1 C1 120.06(16) . . ?
C9 N1 C25 119.11(16) . . ?
C1 N1 C25 120.76(16) . . ?
N1 C1 C2 121.17(17) . . ?
N1 C1 C6 118.95(18) . . ?
C2 C1 C6 119.88(17) . . ?
C3 C2 C1 117.98(18) . . ?
C3 C2 H2B 121.0 . . ?
C1 C2 H2B 121.0 . . ?
F1 C3 C2 117.47(19) . . ?
F1 C3 C4 118.23(19) . . ?
C2 C3 C4 124.3(2) . . ?
C5 C4 C3 117.24(19) . . ?
C5 C4 H4 121.4 . . ?
C3 C4 H4 121.4 . . ?
C4 C5 C6 121.62(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.97(19) . . ?
C5 C6 C7 119.45(17) . . ?
C1 C6 C7 121.56(17) . . ?
O1 C7 C8 122.81(19) . . ?
O1 C7 C6 122.10(18) . . ?
C8 C7 C6 115.09(16) . . ?
C9 C8 C7 120.06(18) . . ?
C9 C8 C10 121.10(17) . . ?
C7 C8 C10 118.83(16) . . ?
N1 C9 C8 124.23(18) . . ?
N1 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
N2 C10 C11 117.63(19) . . ?
N2 C10 C8 123.76(19) . . ?
C11 C10 C8 118.56(18) . . ?
C12 C11 C16 117.5(2) . . ?
C12 C11 C10 121.2(2) . . ?
C16 C11 C10 121.26(19) . . ?
C13 C12 C11 121.2(2) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
O2 C16 C15 118.4(2) . . ?
O2 C16 C11 121.3(2) . . ?
C15 C16 C11 120.3(2) . . ?
N2 C17 C18 111.56(18) . . ?
N2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 112.08(18) . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C17 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C24 118.2(2) . . ?
C20 C19 C18 120.4(2) . . ?
C24 C19 C18 121.3(2) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 119.8(2) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C24 120.1(2) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.8(2) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
N1 C25 C26 112.80(17) . . ?
N1 C25 H25A 109.0 . . ?
C26 C25 H25A 109.0 . . ?
N1 C25 H25B 109.0 . . ?
C26 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C27 C26 C25 113.36(18) . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C32 C27 C28 118.6(2) . . ?
C32 C27 C26 120.8(2) . . ?
C28 C27 C26 120.6(2) . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C27 C28 H28 119.8 . . ?
C30 C29 C28 120.5(3) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 119.5(3) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C32 C31 C30 120.2(3) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 120.8(2) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C2 176.91(19) . . . . ?
C25 N1 C1 C2 -0.1(3) . . . . ?
C9 N1 C1 C6 -2.4(3) . . . . ?
C25 N1 C1 C6 -179.39(18) . . . . ?
N1 C1 C2 C3 -179.4(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C1 C2 C3 F1 177.85(19) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
F1 C3 C4 C5 -177.9(2) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 177.0(2) . . . . ?
N1 C1 C6 C5 -179.32(19) . . . . ?
C2 C1 C6 C5 1.4(3) . . . . ?
N1 C1 C6 C7 2.3(3) . . . . ?
C2 C1 C6 C7 -177.0(2) . . . . ?
C5 C6 C7 O1 0.7(3) . . . . ?
C1 C6 C7 O1 179.1(2) . . . . ?
C5 C6 C7 C8 -179.20(19) . . . . ?
C1 C6 C7 C8 -0.8(3) . . . . ?
O1 C7 C8 C9 179.5(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
O1 C7 C8 C10 -1.9(3) . . . . ?
C6 C7 C8 C10 178.03(18) . . . . ?
C1 N1 C9 C8 1.1(3) . . . . ?
C25 N1 C9 C8 178.12(19) . . . . ?
C7 C8 C9 N1 0.5(3) . . . . ?
C10 C8 C9 N1 -178.11(19) . . . . ?
C17 N2 C10 C11 176.33(16) . . . . ?
C17 N2 C10 C8 -1.2(3) . . . . ?
C9 C8 C10 N2 -95.4(2) . . . . ?
C7 C8 C10 N2 86.0(2) . . . . ?
C9 C8 C10 C11 87.0(2) . . . . ?
C7 C8 C10 C11 -91.6(2) . . . . ?
N2 C10 C11 C12 -178.6(2) . . . . ?
C8 C10 C11 C12 -0.9(3) . . . . ?
N2 C10 C11 C16 -0.9(3) . . . . ?
C8 C10 C11 C16 176.78(17) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
C10 C11 C12 C13 177.5(2) . . . . ?
C11 C12 C13 C14 0.4(4) . . . . ?
C12 C13 C14 C15 0.0(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 O2 -179.2(2) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 O2 179.5(2) . . . . ?
C10 C11 C16 O2 1.8(3) . . . . ?
C12 C11 C16 C15 -0.2(3) . . . . ?
C10 C11 C16 C15 -177.9(2) . . . . ?
C10 N2 C17 C18 114.4(2) . . . . ?
N2 C17 C18 C19 -73.0(2) . . . . ?
C17 C18 C19 C20 -86.4(2) . . . . ?
C17 C18 C19 C24 90.4(2) . . . . ?
C24 C19 C20 C21 0.3(3) . . . . ?
C18 C19 C20 C21 177.2(2) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C21 C22 C23 0.3(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C20 C19 C24 C23 0.2(3) . . . . ?
C18 C19 C24 C23 -176.7(2) . . . . ?
C22 C23 C24 C19 -0.5(3) . . . . ?
C9 N1 C25 C26 -94.9(2) . . . . ?
C1 N1 C25 C26 82.1(2) . . . . ?
N1 C25 C26 C27 65.0(2) . . . . ?
C25 C26 C27 C32 -112.5(2) . . . . ?
C25 C26 C27 C28 67.1(3) . . . . ?
C32 C27 C28 C29 1.1(4) . . . . ?
C26 C27 C28 C29 -178.5(2) . . . . ?
C27 C28 C29 C30 -1.0(4) . . . . ?
C28 C29 C30 C31 0.3(5) . . . . ?
C29 C30 C31 C32 0.2(5) . . . . ?
C30 C31 C32 C27 -0.1(4) . . . . ?
C28 C27 C32 C31 -0.6(4) . . . . ?
C26 C27 C32 C31 179.0(2) . . . . ?

_refine_diff_density_max         0.175
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_av_sm395
_database_code_depnum_ccdc_archive 'CCDC 1016270'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H28 N2 O2'
_chemical_formula_sum            'C32 H28 N2 O2'
_chemical_formula_weight         472.56

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

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                   31.6167(10)
_cell_length_b                   10.4048(3)
_cell_length_c                   16.4565(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.191(2)
_cell_angle_gamma                90.00
_cell_volume                     4938.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5457
_cell_measurement_theta_min      4.987
_cell_measurement_theta_max      50.038

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2000
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9599
_exptl_absorpt_correction_T_max  0.9866
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36127
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0419
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         30.83
_reflns_number_total             7608
_reflns_number_gt                4973
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups and OH groups were allowed to refine. The Uij of the atom 
 pairs C11a/C11b, C12a/C12b, C15a/C15b and C16a/C16b of the disordered 
 o-hydroxyphenyl group were restrained to be equal.
 
 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)+(0.0463P)²+2.4767P] 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         7608
_refine_ls_number_parameters     367
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0835
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1076
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.12882(4) 0.43902(9) 0.20603(6) 0.0257(2) Uani 1 1 d . . .
N2 N 0.19795(4) 0.67839(11) 0.05951(8) 0.0380(3) Uani 1 1 d . A .
O1 O 0.14321(4) 0.40319(10) -0.02895(7) 0.0488(3) Uani 1 1 d . . .
C1 C 0.13843(5) 0.41461(12) 0.04160(8) 0.0291(3) Uani 1 1 d . . .
C2 C 0.14411(4) 0.53493(11) 0.08814(8) 0.0243(2) Uani 1 1 d . A .
C3 C 0.13955(4) 0.54120(11) 0.16675(8) 0.0250(2) Uani 1 1 d . . .
H3 H 0.1441 0.6221 0.1959 0.030 Uiso 1 1 calc R . .
C4 C 0.12083(4) 0.32006(11) 0.16431(8) 0.0249(2) Uani 1 1 d . . .
C5 C 0.10779(5) 0.21338(12) 0.20149(9) 0.0320(3) Uani 1 1 d . . .
H5 H 0.1038 0.2224 0.2554 0.038 Uiso 1 1 calc R . .
C6 C 0.10080(5) 0.09658(13) 0.15962(10) 0.0373(3) Uani 1 1 d . . .
H6 H 0.0917 0.0252 0.1848 0.045 Uiso 1 1 calc R . .
C7 C 0.10668(5) 0.08011(13) 0.08117(10) 0.0409(3) Uani 1 1 d . . .
H7 H 0.1020 -0.0018 0.0534 0.049 Uiso 1 1 calc R . .
C8 C 0.11925(5) 0.18349(13) 0.04430(9) 0.0372(3) Uani 1 1 d . . .
H8 H 0.1233 0.1725 -0.0094 0.045 Uiso 1 1 calc R . .
C9 C 0.12624(4) 0.30508(11) 0.08437(8) 0.0267(2) Uani 1 1 d . . .
C10 C 0.15620(4) 0.65064(12) 0.04775(8) 0.0278(3) Uani 1 1 d . . .
O2A O 0.1756(3) 0.8613(9) -0.0435(7) 0.0507(13) Uani 0.69(3) 1 d PD A 1
H2A H 0.1937 0.8125 -0.0039 0.076 Uiso 0.69(3) 1 calc PR A 1
C11A C 0.1209(3) 0.7341(14) -0.0113(12) 0.0273(8) Uani 0.69(3) 1 d PD A 1
C12A C 0.1321(3) 0.8366(9) -0.0557(7) 0.0346(9) Uani 0.69(3) 1 d PD A 1
C13A C 0.0973(4) 0.9164(10) -0.1119(7) 0.0417(13) Uani 0.69(3) 1 d PD A 1
H13A H 0.1049 0.9856 -0.1411 0.050 Uiso 0.69(3) 1 calc PR A 1
C14A C 0.0518(4) 0.8965(12) -0.1259(9) 0.0436(15) Uani 0.69(3) 1 d PD A 1
H14A H 0.0282 0.9503 -0.1661 0.052 Uiso 0.69(3) 1 calc PR A 1
C15A C 0.0401(3) 0.7986(10) -0.0818(8) 0.0420(10) Uani 0.69(3) 1 d PD A 1
H15A H 0.0087 0.7854 -0.0911 0.050 Uiso 0.69(3) 1 calc PR A 1
C16A C 0.0747(3) 0.7205(11) -0.0239(9) 0.0339(9) Uani 0.69(3) 1 d PD A 1
H16A H 0.0668 0.6558 0.0082 0.041 Uiso 0.69(3) 1 calc PR A 1
O2B O 0.1638(7) 0.8643(19) -0.0596(15) 0.054(3) Uani 0.31(3) 1 d PD A 2
H2B H 0.1835 0.8155 -0.0226 0.081 Uiso 0.31(3) 1 calc PR A 2
C11B C 0.1145(7) 0.735(3) -0.013(3) 0.0273(8) Uani 0.31(3) 1 d PD A 2
C12B C 0.1220(6) 0.838(2) -0.0620(17) 0.0346(9) Uani 0.31(3) 1 d PD A 2
C13B C 0.0845(7) 0.908(2) -0.1201(17) 0.041(4) Uani 0.31(3) 1 d PD A 2
H13B H 0.0892 0.9741 -0.1557 0.050 Uiso 0.31(3) 1 calc PR A 2
C14B C 0.0407(7) 0.883(3) -0.126(2) 0.049(4) Uani 0.31(3) 1 d PD A 2
H14B H 0.0155 0.9347 -0.1642 0.058 Uiso 0.31(3) 1 calc PR A 2
C15B C 0.0323(6) 0.784(3) -0.0791(19) 0.0420(10) Uani 0.31(3) 1 d PD A 2
H15B H 0.0020 0.7684 -0.0830 0.050 Uiso 0.31(3) 1 calc PR A 2
C16B C 0.0692(7) 0.707(3) -0.026(2) 0.0339(9) Uani 0.31(3) 1 d PD A 2
H16B H 0.0633 0.6339 0.0023 0.041 Uiso 0.31(3) 1 calc PR A 2
C17 C 0.12410(5) 0.45781(13) 0.29091(8) 0.0329(3) Uani 1 1 d . . .
H17A H 0.1408 0.5371 0.3198 0.039 Uiso 1 1 calc R . .
H17B H 0.1390 0.3848 0.3310 0.039 Uiso 1 1 calc R . .
C18 C 0.07373(5) 0.46811(14) 0.27927(10) 0.0388(3) Uani 1 1 d . . .
H18A H 0.0574 0.3869 0.2536 0.047 Uiso 1 1 calc R . .
H18B H 0.0730 0.4799 0.3384 0.047 Uiso 1 1 calc R . .
C19 C 0.04873(5) 0.57778(13) 0.21988(9) 0.0336(3) Uani 1 1 d . . .
C20 C 0.05839(5) 0.70375(14) 0.25011(10) 0.0386(3) Uani 1 1 d . . .
H20 H 0.0806 0.7200 0.3089 0.046 Uiso 1 1 calc R . .
C21 C 0.03606(5) 0.80511(15) 0.19570(12) 0.0457(4) Uani 1 1 d . . .
H21 H 0.0429 0.8906 0.2175 0.055 Uiso 1 1 calc R . .
C22 C 0.00397(6) 0.78398(18) 0.11026(12) 0.0520(4) Uani 1 1 d . . .
H22 H -0.0111 0.8543 0.0728 0.062 Uiso 1 1 calc R . .
C23 C -0.00614(6) 0.65959(19) 0.07931(11) 0.0534(4) Uani 1 1 d . . .
H23 H -0.0285 0.6441 0.0204 0.064 Uiso 1 1 calc R . .
C24 C 0.01614(5) 0.55727(16) 0.13376(11) 0.0436(4) Uani 1 1 d . . .
H24 H 0.0090 0.4720 0.1118 0.052 Uiso 1 1 calc R . .
C25 C 0.23797(5) 0.60631(16) 0.11999(11) 0.0444(4) Uani 1 1 d . . .
H25A H 0.2571 0.5785 0.0884 0.053 Uiso 1 1 calc R A .
H25B H 0.2275 0.5287 0.1413 0.053 Uiso 1 1 calc R . .
C26 C 0.26688(5) 0.69175(18) 0.19954(13) 0.0572(5) Uani 1 1 d . A .
H26A H 0.2967 0.6481 0.2346 0.069 Uiso 1 1 calc R . .
H26B H 0.2740 0.7734 0.1769 0.069 Uiso 1 1 calc R . .
C27 C 0.24315(5) 0.72166(15) 0.25969(11) 0.0459(4) Uani 1 1 d . . .
C28 C 0.25123(6) 0.64750(18) 0.33533(12) 0.0587(5) Uani 1 1 d . A .
H28 H 0.2730 0.5790 0.3499 0.070 Uiso 1 1 calc R . .
C29 C 0.22838(7) 0.67135(19) 0.38948(12) 0.0641(5) Uani 1 1 d . . .
H29 H 0.2345 0.6193 0.4405 0.077 Uiso 1 1 calc R A .
C30 C 0.19699(7) 0.76946(18) 0.37015(12) 0.0577(4) Uani 1 1 d . A .
H30 H 0.1812 0.7858 0.4074 0.069 Uiso 1 1 calc R . .
C31 C 0.18849(6) 0.84399(16) 0.29647(12) 0.0532(4) Uani 1 1 d . . .
H31 H 0.1668 0.9126 0.2830 0.064 Uiso 1 1 calc R A .
C32 C 0.21101(5) 0.82078(15) 0.24127(12) 0.0483(4) Uani 1 1 d . A .
H32 H 0.2044 0.8732 0.1902 0.058 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
N1 C3 1.3574(15) . ?
N1 C4 1.3875(15) . ?
N1 C17 1.4774(14) . ?
N2 C10 1.2860(16) . ?
N2 C25 1.4567(19) . ?
O1 C1 1.2364(15) . ?
C1 C2 1.4400(17) . ?
C1 C9 1.4714(17) . ?
C2 C3 1.3607(16) . ?
C2 C10 1.4987(16) . ?
C3 H3 0.9500 . ?
C4 C9 1.4030(16) . ?
C4 C5 1.4082(17) . ?
C5 C6 1.3696(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3714(19) . ?
C7 H7 0.9500 . ?
C8 C9 1.4017(17) . ?
C8 H8 0.9500 . ?
C10 C11A 1.435(8) . ?
C10 C11B 1.561(16) . ?
O2A C12A 1.330(4) . ?
O2A H2A 0.8400 . ?
C11A C16A 1.396(4) . ?
C11A C12A 1.417(3) . ?
C12A C13A 1.387(4) . ?
C13A C14A 1.377(5) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.386(4) . ?
C14A H14A 0.9500 . ?
C15A C16A 1.382(4) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
O2B C12B 1.332(7) . ?
O2B H2B 0.8400 . ?
C11B C16B 1.390(7) . ?
C11B C12B 1.419(7) . ?
C12B C13B 1.386(7) . ?
C13B C14B 1.374(8) . ?
C13B H13B 0.9500 . ?
C14B C15B 1.381(8) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.387(7) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C17 C18 1.5278(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.500(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.385(2) . ?
C19 C20 1.3908(19) . ?
C20 C21 1.376(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.380(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.384(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.536(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.499(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.391(2) . ?
C27 C28 1.396(3) . ?
C28 C29 1.380(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.367(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.370(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C4 119.57(10) . . ?
C3 N1 C17 119.23(10) . . ?
C4 N1 C17 121.16(10) . . ?
C10 N2 C25 122.54(12) . . ?
O1 C1 C2 123.12(11) . . ?
O1 C1 C9 122.11(11) . . ?
C2 C1 C9 114.76(10) . . ?
C3 C2 C1 120.58(11) . . ?
C3 C2 C10 121.93(11) . . ?
C1 C2 C10 117.47(10) . . ?
N1 C3 C2 124.03(11) . . ?
N1 C3 H3 118.0 . . ?
C2 C3 H3 118.0 . . ?
N1 C4 C9 119.71(10) . . ?
N1 C4 C5 120.97(11) . . ?
C9 C4 C5 119.32(11) . . ?
C6 C5 C4 119.76(12) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 121.46(12) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C6 119.22(13) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.20(13) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 119.02(11) . . ?
C8 C9 C1 119.71(11) . . ?
C4 C9 C1 121.27(11) . . ?
N2 C10 C11A 115.6(3) . . ?
N2 C10 C2 123.11(12) . . ?
C11A C10 C2 121.2(4) . . ?
N2 C10 C11B 121.1(6) . . ?
C11A C10 C11B 5.6(9) . . ?
C2 C10 C11B 115.8(6) . . ?
C16A C11A C12A 117.9(4) . . ?
C16A C11A C10 121.1(5) . . ?
C12A C11A C10 120.9(5) . . ?
O2A C12A C13A 118.3(4) . . ?
O2A C12A C11A 122.0(4) . . ?
C13A C12A C11A 119.7(4) . . ?
C14A C13A C12A 120.8(5) . . ?
C14A C13A H13A 119.6 . . ?
C12A C13A H13A 119.6 . . ?
C13A C14A C15A 120.5(4) . . ?
C13A C14A H14A 119.8 . . ?
C15A C14A H14A 119.8 . . ?
C16A C15A C14A 119.2(4) . . ?
C16A C15A H15A 120.4 . . ?
C14A C15A H15A 120.4 . . ?
C15A C16A C11A 121.8(4) . . ?
C15A C16A H16A 119.1 . . ?
C11A C16A H16A 119.1 . . ?
C12B O2B H2B 109.5 . . ?
C16B C11B C12B 118.4(9) . . ?
C16B C11B C10 121.8(11) . . ?
C12B C11B C10 119.7(11) . . ?
O2B C12B C13B 118.1(10) . . ?
O2B C12B C11B 122.1(9) . . ?
C13B C12B C11B 119.6(8) . . ?
C14B C13B C12B 120.1(8) . . ?
C14B C13B H13B 119.9 . . ?
C12B C13B H13B 119.9 . . ?
C13B C14B C15B 121.4(9) . . ?
C13B C14B H14B 119.3 . . ?
C15B C14B H14B 119.3 . . ?
C14B C15B C16B 118.7(9) . . ?
C14B C15B H15B 120.6 . . ?
C16B C15B H15B 120.6 . . ?
C15B C16B C11B 121.4(9) . . ?
C15B C16B H16B 119.3 . . ?
C11B C16B H16B 119.3 . . ?
N1 C17 C18 113.25(11) . . ?
N1 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N1 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 112.28(11) . . ?
C19 C18 H18A 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C24 C19 C20 118.25(14) . . ?
C24 C19 C18 121.46(13) . . ?
C20 C19 C18 120.28(13) . . ?
C21 C20 C19 120.70(14) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C22 C21 C20 120.69(15) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C21 C22 C23 119.36(16) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C22 C23 C24 120.22(16) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C23 C24 C19 120.78(15) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?
N2 C25 C26 109.35(13) . . ?
N2 C25 H25A 109.8 . . ?
C26 C25 H25A 109.8 . . ?
N2 C25 H25B 109.8 . . ?
C26 C25 H25B 109.8 . . ?
H25A C25 H25B 108.3 . . ?
C27 C26 C25 113.51(12) . . ?
C27 C26 H26A 108.9 . . ?
C25 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C25 C26 H26B 108.9 . . ?
H26A C26 H26B 107.7 . . ?
C32 C27 C28 117.03(16) . . ?
C32 C27 C26 121.90(16) . . ?
C28 C27 C26 121.03(16) . . ?
C29 C28 C27 121.55(17) . . ?
C29 C28 H28 119.2 . . ?
C27 C28 H28 119.2 . . ?
C30 C29 C28 120.41(19) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 119.26(18) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C30 C31 C32 120.96(17) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C27 120.80(17) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.36(13) . . . . ?
C9 C1 C2 C3 1.84(17) . . . . ?
O1 C1 C2 C10 0.25(19) . . . . ?
C9 C1 C2 C10 -179.55(11) . . . . ?
C4 N1 C3 C2 -1.45(18) . . . . ?
C17 N1 C3 C2 -179.10(11) . . . . ?
C1 C2 C3 N1 -1.20(19) . . . . ?
C10 C2 C3 N1 -179.75(11) . . . . ?
C3 N1 C4 C9 3.26(17) . . . . ?
C17 N1 C4 C9 -179.14(11) . . . . ?
C3 N1 C4 C5 -177.38(11) . . . . ?
C17 N1 C4 C5 0.23(17) . . . . ?
N1 C4 C5 C6 -179.00(12) . . . . ?
C9 C4 C5 C6 0.36(19) . . . . ?
C4 C5 C6 C7 0.6(2) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C4 0.9(2) . . . . ?
C7 C8 C9 C1 -178.30(13) . . . . ?
N1 C4 C9 C8 178.30(12) . . . . ?
C5 C4 C9 C8 -1.07(18) . . . . ?
N1 C4 C9 C1 -2.51(18) . . . . ?
C5 C4 C9 C1 178.11(12) . . . . ?
O1 C1 C9 C8 -0.6(2) . . . . ?
C2 C1 C9 C8 179.16(12) . . . . ?
O1 C1 C9 C4 -179.82(13) . . . . ?
C2 C1 C9 C4 -0.02(17) . . . . ?
C25 N2 C10 C11A 177.6(10) . . . . ?
C25 N2 C10 C2 -5.8(2) . . . . ?
C25 N2 C10 C11B 176(2) . . . . ?
C3 C2 C10 N2 94.79(15) . . . . ?
C1 C2 C10 N2 -83.80(16) . . . . ?
C3 C2 C10 C11A -88.8(10) . . . . ?
C1 C2 C10 C11A 92.6(10) . . . . ?
C3 C2 C10 C11B -87(2) . . . . ?
C1 C2 C10 C11B 94(2) . . . . ?
N2 C10 C11A C16A -174.7(15) . . . . ?
C2 C10 C11A C16A 9(2) . . . . ?
C11B C10 C11A C16A -8(27) . . . . ?
N2 C10 C11A C12A 2(2) . . . . ?
C2 C10 C11A C12A -174.2(12) . . . . ?
C11B C10 C11A C12A 169(30) . . . . ?
C16A C11A C12A O2A 176.0(16) . . . . ?
C10 C11A C12A O2A -1(3) . . . . ?
C16A C11A C12A C13A -2(3) . . . . ?
C10 C11A C12A C13A -179.5(14) . . . . ?
O2A C12A C13A C14A -178.9(13) . . . . ?
C11A C12A C13A C14A -1(2) . . . . ?
C12A C13A C14A C15A 2(2) . . . . ?
C13A C14A C15A C16A 0(2) . . . . ?
C14A C15A C16A C11A -3(2) . . . . ?
C12A C11A C16A C15A 4(3) . . . . ?
C10 C11A C16A C15A -178.8(15) . . . . ?
N2 C10 C11B C16B -180(3) . . . . ?
C11A C10 C11B C16B 167(33) . . . . ?
C2 C10 C11B C16B 2(5) . . . . ?
N2 C10 C11B C12B 5(5) . . . . ?
C11A C10 C11B C12B -9(25) . . . . ?
C2 C10 C11B C12B -173(3) . . . . ?
C16B C11B C12B O2B -174(4) . . . . ?
C10 C11B C12B O2B 2(6) . . . . ?
C16B C11B C12B C13B 1(6) . . . . ?
C10 C11B C12B C13B 176(3) . . . . ?
O2B C12B C13B C14B 178(3) . . . . ?
C11B C12B C13B C14B 4(5) . . . . ?
C12B C13B C14B C15B -3(5) . . . . ?
C13B C14B C15B C16B -1(6) . . . . ?
C14B C15B C16B C11B 6(6) . . . . ?
C12B C11B C16B C15B -5(7) . . . . ?
C10 C11B C16B C15B 179(3) . . . . ?
C3 N1 C17 C18 100.31(13) . . . . ?
C4 N1 C17 C18 -77.31(14) . . . . ?
N1 C17 C18 C19 -59.26(15) . . . . ?
C17 C18 C19 C24 106.17(15) . . . . ?
C17 C18 C19 C20 -72.91(15) . . . . ?
C24 C19 C20 C21 0.0(2) . . . . ?
C18 C19 C20 C21 179.16(12) . . . . ?
C19 C20 C21 C22 -0.4(2) . . . . ?
C20 C21 C22 C23 0.6(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C19 0.1(2) . . . . ?
C20 C19 C24 C23 0.1(2) . . . . ?
C18 C19 C24 C23 -179.02(13) . . . . ?
C10 N2 C25 C26 -111.82(15) . . . . ?
N2 C25 C26 C27 68.48(18) . . . . ?
C25 C26 C27 C32 -83.1(2) . . . . ?
C25 C26 C27 C28 94.52(19) . . . . ?
C32 C27 C28 C29 0.0(2) . . . . ?
C26 C27 C28 C29 -177.71(16) . . . . ?
C27 C28 C29 C30 -0.1(3) . . . . ?
C28 C29 C30 C31 -0.1(3) . . . . ?
C29 C30 C31 C32 0.4(3) . . . . ?
C30 C31 C32 C27 -0.5(2) . . . . ?
C28 C27 C32 C31 0.3(2) . . . . ?
C26 C27 C32 C31 178.00(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.83
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_av_sm827
_database_code_depnum_ccdc_archive 'CCDC 1016271'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 F N3 O2'
_chemical_formula_sum            'C21 H14 F N3 O2'
_chemical_formula_weight         359.35

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.2321(11)
_cell_length_b                   6.7111(5)
_cell_length_c                   33.287(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3402.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2960
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      26.08

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6437
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex Kappa II-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23600
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_av_R_equivalents  0.0618
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         1.812
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4304
_reflns_number_gt                2820
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups).
 
 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     
'w=1/[σ²(Fo²)+(0.0461P)²+0.5757P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4304
_refine_ls_number_parameters     266
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.71256(9) 0.15557(19) 0.50862(4) 0.0342(3) Uani 1 1 d . . . . .
N2 N 0.80180(8) 0.15312(19) 0.50398(4) 0.0316(3) Uani 1 1 d . . . . .
N3 N 0.90601(8) 0.16017(18) 0.45007(4) 0.0290(3) Uani 1 1 d . . . . .
O2 O 0.81629(9) 0.38268(19) 0.32829(4) 0.0527(4) Uani 1 1 d . . . . .
C3A C 1.0002(3) 0.1545(9) 0.39309(19) 0.0311(4) Uani 0.869(17) 1 d D . P A 1
C4A C 1.0667(4) 0.2830(7) 0.40543(16) 0.0375(8) Uani 0.869(17) 1 d D . P A 1
H4A H 1.0547 0.3807 0.4253 0.045 Uiso 0.869(17) 1 calc R U P A 1
C5A C 1.1498(4) 0.2702(8) 0.3891(2) 0.0449(9) Uani 0.869(17) 1 d D . P A 1
H5A H 1.1943 0.3604 0.3974 0.054 Uiso 0.869(17) 1 calc R U P A 1
C6A C 1.1682(3) 0.1261(11) 0.3606(2) 0.0476(8) Uani 0.869(17) 1 d D . P A 1
H6A H 1.2251 0.1198 0.3490 0.057 Uiso 0.869(17) 1 calc R U P A 1
C7A C 1.1046(3) -0.0086(9) 0.34902(15) 0.0414(8) Uani 0.869(17) 1 d D . P A 1
H7A H 1.1178 -0.1114 0.3304 0.050 Uiso 0.869(17) 1 calc R U P A 1
C8A C 1.0210(3) 0.0092(8) 0.36510(16) 0.0328(7) Uani 0.869(17) 1 d D . P A 1
O1A O 0.9559(3) -0.1307(7) 0.35509(12) 0.0359(5) Uani 0.869(17) 1 d D . P A 1
C9A C 0.9205(4) -0.0965(7) 0.31720(12) 0.0346(5) Uani 0.869(17) 1 d D . P A 1
C10A C 0.9369(4) -0.2366(7) 0.28761(13) 0.0466(6) Uani 0.869(17) 1 d D . P A 1
H10A H 0.9690 -0.3540 0.2938 0.056 Uiso 0.869(17) 1 calc R U P A 1
C11A C 0.9064(3) -0.2047(7) 0.24906(13) 0.0553(9) Uani 0.869(17) 1 d D . P A 1
H11A H 0.9166 -0.2996 0.2284 0.066 Uiso 0.869(17) 1 calc R U P A 1
C12A C 0.8609(3) -0.0330(7) 0.24145(10) 0.0509(9) Uani 0.869(17) 1 d D . P A 1
C13A C 0.8421(3) 0.1049(7) 0.27035(11) 0.0417(7) Uani 0.869(17) 1 d D . P A 1
H13A H 0.8095 0.2210 0.2638 0.050 Uiso 0.869(17) 1 calc R U P A 1
C14A C 0.8711(4) 0.0739(6) 0.30950(10) 0.0324(6) Uani 0.869(17) 1 d D . P A 1
F1A F 0.8319(3) 0.0005(9) 0.20350(10) 0.0764(11) Uani 0.869(17) 1 d D . P A 1
C3B C 1.001(2) 0.162(6) 0.3926(12) 0.0311(4) Uani 0.131(17) 1 d DG . P A 2
C4B C 1.061(3) 0.312(5) 0.4015(12) 0.0375(8) Uani 0.131(17) 1 d DG . P A 2
H4B H 1.0433 0.4234 0.4172 0.045 Uiso 0.131(17) 1 calc R U P A 2
C5B C 1.147(3) 0.300(6) 0.3872(15) 0.0449(9) Uani 0.131(17) 1 d DG . P A 2
H5B H 1.1874 0.4025 0.3933 0.054 Uiso 0.131(17) 1 calc R U P A 2
C6B C 1.172(2) 0.138(7) 0.3641(15) 0.0476(8) Uani 0.131(17) 1 d DG . P A 2
H6B H 1.2308 0.1291 0.3544 0.057 Uiso 0.131(17) 1 calc R U P A 2
C7B C 1.112(2) -0.012(6) 0.3553(11) 0.0414(8) Uani 0.131(17) 1 d DG . P A 2
H7B H 1.1299 -0.1234 0.3395 0.050 Uiso 0.131(17) 1 calc R U P A 2
C8B C 1.0267(19) 0.000(6) 0.3695(11) 0.0328(7) Uani 0.131(17) 1 d DG . P A 2
O1B O 0.964(2) -0.144(5) 0.3596(7) 0.0359(5) Uani 0.131(17) 1 d D . P A 2
C9B C 0.928(2) -0.115(5) 0.3217(7) 0.0346(5) Uani 0.131(17) 1 d DG . P A 2
C10B C 0.942(2) -0.261(5) 0.2929(8) 0.0466(6) Uani 0.131(17) 1 d DG . P A 2
H10B H 0.9779 -0.3733 0.2989 0.056 Uiso 0.131(17) 1 calc R U P A 2
C11B C 0.903(2) -0.244(4) 0.2552(7) 0.0553(9) Uani 0.131(17) 1 d DG . P A 2
H11B H 0.9128 -0.3442 0.2355 0.066 Uiso 0.131(17) 1 calc R U P A 2
C12B C 0.8510(17) -0.080(4) 0.2464(5) 0.0509(9) Uani 0.131(17) 1 d DG . P A 2
C13B C 0.8372(19) 0.066(4) 0.2752(6) 0.0417(7) Uani 0.131(17) 1 d DG . P A 2
H13B H 0.8014 0.1782 0.2692 0.050 Uiso 0.131(17) 1 calc R U P A 2
C14B C 0.876(2) 0.049(4) 0.3129(6) 0.0324(6) Uani 0.131(17) 1 d DG . P A 2
F1B F 0.8097(16) -0.070(4) 0.2108(6) 0.0764(11) Uani 0.131(17) 1 d D . P A 2
C1 C 0.82397(9) 0.1622(2) 0.46471(4) 0.0271(3) Uani 1 1 d . . . . .
C2 C 0.91023(9) 0.1648(2) 0.40995(5) 0.0284(3) Uani 1 1 d . . . . .
C15 C 0.84303(10) 0.2232(3) 0.34042(5) 0.0342(4) Uani 1 1 d . . . . .
C16 C 0.83612(9) 0.1807(2) 0.38456(5) 0.0285(3) Uani 1 1 d . . . . .
C17 C 0.75247(10) 0.1857(2) 0.40110(5) 0.0291(3) Uani 1 1 d . . . . .
H17 H 0.7018 0.1984 0.3846 0.035 Uiso 1 1 calc R U . . .
C18 C 0.74564(10) 0.1713(2) 0.44265(4) 0.0277(3) Uani 1 1 d . . . . .
C19 C 0.67813(10) 0.1659(2) 0.47216(5) 0.0308(3) Uani 1 1 d . . . . .
C20 C 0.85903(12) 0.1468(3) 0.53847(5) 0.0457(5) Uani 1 1 d . . . . .
H20A H 0.9177 0.1040 0.5301 0.069 Uiso 1 1 calc R U . . .
H20B H 0.8356 0.0525 0.5582 0.069 Uiso 1 1 calc R U . . .
H20C H 0.8626 0.2798 0.5505 0.069 Uiso 1 1 calc R U . . .
C21 C 0.58118(10) 0.1691(3) 0.46655(6) 0.0393(4) Uani 1 1 d . . . . .
H21A H 0.5582 0.0331 0.4684 0.059 Uiso 1 1 calc R U . . .
H21B H 0.5672 0.2245 0.4401 0.059 Uiso 1 1 calc R U . . .
H21C H 0.5543 0.2519 0.4875 0.059 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C19 1.324(2) . ?
N1 N2 1.3682(18) . ?
N2 C1 1.3513(18) . ?
N2 C20 1.442(2) . ?
N3 C2 1.3373(19) . ?
N3 C1 1.3415(18) . ?
O2 C15 1.2143(19) . ?
C3A C8A 1.386(3) . ?
C3A C4A 1.392(3) . ?
C3A C2 1.483(6) . ?
C4A C5A 1.380(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.383(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.381(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.385(2) . ?
C7A H7A 0.9500 . ?
C8A O1A 1.405(2) . ?
O1A C9A 1.391(2) . ?
C9A C10A 1.384(3) . ?
C9A C14A 1.393(3) . ?
C10A C11A 1.382(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.368(3) . ?
C11A H11A 0.9500 . ?
C12A F1A 1.357(2) . ?
C12A C13A 1.365(3) . ?
C13A C14A 1.392(3) . ?
C13A H13A 0.9500 . ?
C14A C15 1.498(4) . ?
C3B C4B 1.3900 . ?
C3B C8B 1.3900 . ?
C3B C2 1.50(3) . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B C7B 1.3900 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.3900 . ?
C7B H7B 0.9500 . ?
C8B O1B 1.400(8) . ?
O1B C9B 1.386(8) . ?
C9B C10B 1.3900 . ?
C9B C14B 1.3900 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
C12B F1B 1.344(8) . ?
C12B C13B 1.3900 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15 1.57(2) . ?
C1 C18 1.402(2) . ?
C2 C16 1.414(2) . ?
C15 C16 1.501(2) . ?
C16 C17 1.388(2) . ?
C17 C18 1.390(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.423(2) . ?
C19 C21 1.489(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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
C19 N1 N2 106.89(12) . . ?
C1 N2 N1 110.91(13) . . ?
C1 N2 C20 128.33(13) . . ?
N1 N2 C20 120.73(13) . . ?
C2 N3 C1 114.04(12) . . ?
C8A C3A C4A 117.89(17) . . ?
C8A C3A C2 119.9(3) . . ?
C4A C3A C2 122.1(3) . . ?
C5A C4A C3A 120.8(2) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C4A C5A C6A 120.0(2) . . ?
C4A C5A H5A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C7A C6A C5A 120.47(19) . . ?
C7A C6A H6A 119.8 . . ?
C5A C6A H6A 119.8 . . ?
C6A C7A C8A 118.7(2) . . ?
C6A C7A H7A 120.6 . . ?
C8A C7A H7A 120.6 . . ?
C7A C8A C3A 122.05(18) . . ?
C7A C8A O1A 119.9(2) . . ?
C3A C8A O1A 117.9(2) . . ?
C9A O1A C8A 112.3(2) . . ?
C10A C9A O1A 117.6(2) . . ?
C10A C9A C14A 121.62(18) . . ?
O1A C9A C14A 120.8(2) . . ?
C11A C10A C9A 119.7(2) . . ?
C11A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C12A C11A C10A 118.2(2) . . ?
C12A C11A H11A 120.9 . . ?
C10A C11A H11A 120.9 . . ?
F1A C12A C13A 118.4(2) . . ?
F1A C12A C11A 118.5(2) . . ?
C13A C12A C11A 123.2(2) . . ?
C12A C13A C14A 119.5(2) . . ?
C12A C13A H13A 120.3 . . ?
C14A C13A H13A 120.3 . . ?
C13A C14A C9A 117.81(18) . . ?
C13A C14A C15 116.9(2) . . ?
C9A C14A C15 125.2(2) . . ?
C4B C3B C8B 120.0 . . ?
C4B C3B C2 121.1(18) . . ?
C8B C3B C2 118.8(18) . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C7B C6B C5B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C8B C7B C6B 120.0 . . ?
C8B C7B H7B 120.0 . . ?
C6B C7B H7B 120.0 . . ?
C7B C8B C3B 120.0 . . ?
C7B C8B O1B 121.2(10) . . ?
C3B C8B O1B 118.8(10) . . ?
C9B O1B C8B 112.5(14) . . ?
O1B C9B C10B 117.8(10) . . ?
O1B C9B C14B 122.1(10) . . ?
C10B C9B C14B 120.0 . . ?
C11B C10B C9B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
F1B C12B C11B 119.8(10) . . ?
F1B C12B C13B 120.1(10) . . ?
C11B C12B C13B 120.0 . . ?
C12B C13B C14B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C13B C14B C9B 120.0 . . ?
C13B C14B C15 109.2(12) . . ?
C9B C14B C15 130.5(12) . . ?
N3 C1 N2 125.72(14) . . ?
N3 C1 C18 127.06(14) . . ?
N2 C1 C18 107.21(13) . . ?
N3 C2 C16 124.07(13) . . ?
N3 C2 C3A 114.9(3) . . ?
C16 C2 C3A 121.0(3) . . ?
N3 C2 C3B 115.4(15) . . ?
C16 C2 C3B 120.4(16) . . ?
O2 C15 C14A 117.2(2) . . ?
O2 C15 C16 117.99(14) . . ?
C14A C15 C16 124.5(2) . . ?
O2 C15 C14B 124.8(9) . . ?
C16 C15 C14B 116.9(10) . . ?
C17 C16 C2 119.83(14) . . ?
C17 C16 C15 116.62(13) . . ?
C2 C16 C15 122.93(13) . . ?
C16 C17 C18 117.48(14) . . ?
C16 C17 H17 121.3 . . ?
C18 C17 H17 121.3 . . ?
C17 C18 C1 117.41(13) . . ?
C17 C18 C19 137.97(14) . . ?
C1 C18 C19 104.61(13) . . ?
N1 C19 C18 110.37(14) . . ?
N1 C19 C21 120.57(14) . . ?
C18 C19 C21 129.06(15) . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C19 N1 N2 C1 0.09(16) . . . . ?
C19 N1 N2 C20 178.60(14) . . . . ?
C8A C3A C4A C5A 2.4(3) . . . . ?
C2 C3A C4A C5A -179.8(5) . . . . ?
C3A C4A C5A C6A -1.2(3) . . . . ?
C4A C5A C6A C7A -1.5(3) . . . . ?
C5A C6A C7A C8A 2.8(3) . . . . ?
C6A C7A C8A C3A -1.6(3) . . . . ?
C6A C7A C8A O1A -177.4(5) . . . . ?
C4A C3A C8A C7A -1.0(3) . . . . ?
C2 C3A C8A C7A -178.9(5) . . . . ?
C4A C3A C8A O1A 174.9(5) . . . . ?
C2 C3A C8A O1A -3.0(5) . . . . ?
C7A C8A O1A C9A -77.8(5) . . . . ?
C3A C8A O1A C9A 106.1(3) . . . . ?
C8A O1A C9A C10A 112.9(4) . . . . ?
C8A O1A C9A C14A -66.5(5) . . . . ?
O1A C9A C10A C11A -177.2(5) . . . . ?
C14A C9A C10A C11A 2.2(3) . . . . ?
C9A C10A C11A C12A 0.4(3) . . . . ?
C10A C11A C12A F1A 179.0(3) . . . . ?
C10A C11A C12A C13A -2.1(4) . . . . ?
F1A C12A C13A C14A 180.0(3) . . . . ?
C11A C12A C13A C14A 1.1(4) . . . . ?
C12A C13A C14A C9A 1.5(3) . . . . ?
C12A C13A C14A C15 -175.8(4) . . . . ?
C10A C9A C14A C13A -3.2(3) . . . . ?
O1A C9A C14A C13A 176.2(5) . . . . ?
C10A C9A C14A C15 173.9(5) . . . . ?
O1A C9A C14A C15 -6.7(5) . . . . ?
C8B C3B C4B C5B 0.0 . . . . ?
C2 C3B C4B C5B 176(4) . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C7B 0.0 . . . . ?
C5B C6B C7B C8B 0.0 . . . . ?
C6B C7B C8B C3B 0.0 . . . . ?
C6B C7B C8B O1B 177(4) . . . . ?
C4B C3B C8B C7B 0.0 . . . . ?
C2 C3B C8B C7B -176(4) . . . . ?
C4B C3B C8B O1B -177(3) . . . . ?
C2 C3B C8B O1B 7(3) . . . . ?
C7B C8B O1B C9B -81(4) . . . . ?
C3B C8B O1B C9B 97(2) . . . . ?
C8B O1B C9B C10B 117(2) . . . . ?
C8B O1B C9B C14B -67(3) . . . . ?
O1B C9B C10B C11B 176(3) . . . . ?
C14B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B F1B -176(3) . . . . ?
C10B C11B C12B C13B 0.0 . . . . ?
F1B C12B C13B C14B 176(3) . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C9B 0.0 . . . . ?
C12B C13B C14B C15 -175(3) . . . . ?
O1B C9B C14B C13B -176(3) . . . . ?
C10B C9B C14B C13B 0.0 . . . . ?
O1B C9B C14B C15 -2(3) . . . . ?
C10B C9B C14B C15 174(3) . . . . ?
C2 N3 C1 N2 178.12(14) . . . . ?
C2 N3 C1 C18 -1.0(2) . . . . ?
N1 N2 C1 N3 -179.15(13) . . . . ?
C20 N2 C1 N3 2.5(2) . . . . ?
N1 N2 C1 C18 0.08(16) . . . . ?
C20 N2 C1 C18 -178.28(15) . . . . ?
C1 N3 C2 C16 3.1(2) . . . . ?
C1 N3 C2 C3A -177.7(3) . . . . ?
C1 N3 C2 C3B -179.9(16) . . . . ?
C8A C3A C2 N3 125.4(3) . . . . ?
C4A C3A C2 N3 -52.3(6) . . . . ?
C8A C3A C2 C16 -55.3(5) . . . . ?
C4A C3A C2 C16 126.9(4) . . . . ?
C8A C3A C2 C3B -130(45) . . . . ?
C4A C3A C2 C3B 52(44) . . . . ?
C4B C3B C2 N3 -60(3) . . . . ?
C8B C3B C2 N3 115.5(18) . . . . ?
C4B C3B C2 C16 117(2) . . . . ?
C8B C3B C2 C16 -67(2) . . . . ?
C4B C3B C2 C3A -137(46) . . . . ?
C8B C3B C2 C3A 39(43) . . . . ?
C13A C14A C15 O2 -17.6(5) . . . . ?
C9A C14A C15 O2 165.3(3) . . . . ?
C13A C14A C15 C16 155.1(2) . . . . ?
C9A C14A C15 C16 -22.0(5) . . . . ?
C13A C14A C15 C14B 165(12) . . . . ?
C9A C14A C15 C14B -12(12) . . . . ?
C13B C14B C15 O2 -25(2) . . . . ?
C9B C14B C15 O2 160.7(17) . . . . ?
C13B C14B C15 C14A -22(11) . . . . ?
C9B C14B C15 C14A 164(14) . . . . ?
C13B C14B C15 C16 148.8(12) . . . . ?
C9B C14B C15 C16 -26(3) . . . . ?
N3 C2 C16 C17 -2.2(2) . . . . ?
C3A C2 C16 C17 178.6(3) . . . . ?
C3B C2 C16 C17 -179.1(17) . . . . ?
N3 C2 C16 C15 168.44(14) . . . . ?
C3A C2 C16 C15 -10.8(3) . . . . ?
C3B C2 C16 C15 -8.4(17) . . . . ?
O2 C15 C16 C17 58.9(2) . . . . ?
C14A C15 C16 C17 -113.7(3) . . . . ?
C14B C15 C16 C17 -115.2(15) . . . . ?
O2 C15 C16 C2 -112.02(18) . . . . ?
C14A C15 C16 C2 75.3(3) . . . . ?
C14B C15 C16 C2 73.8(15) . . . . ?
C2 C16 C17 C18 -1.0(2) . . . . ?
C15 C16 C17 C18 -172.24(13) . . . . ?
C16 C17 C18 C1 2.9(2) . . . . ?
C16 C17 C18 C19 -178.64(16) . . . . ?
N3 C1 C18 C17 -2.0(2) . . . . ?
N2 C1 C18 C17 178.74(12) . . . . ?
N3 C1 C18 C19 179.01(14) . . . . ?
N2 C1 C18 C19 -0.21(16) . . . . ?
N2 N1 C19 C18 -0.23(16) . . . . ?
N2 N1 C19 C21 179.38(13) . . . . ?
C17 C18 C19 N1 -178.33(16) . . . . ?
C1 C18 C19 N1 0.28(16) . . . . ?
C17 C18 C19 C21 2.1(3) . . . . ?
C1 C18 C19 C21 -179.29(15) . . . . ?

_refine_diff_density_max         0.254
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_is_sm406
_database_code_depnum_ccdc_archive 'CCDC 1016272'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H32 N2 O2'
_chemical_formula_sum            'C28 H32 N2 O2'
_chemical_formula_weight         428.56

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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

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                   23.8305(13)
_cell_length_b                   9.8495(5)
_cell_length_c                   19.7081(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.587(3)
_cell_angle_gamma                90.00
_cell_volume                     4514.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1416
_cell_measurement_theta_min      4.873
_cell_measurement_theta_max      43.343

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1840
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9519
_exptl_absorpt_correction_T_max  0.9968
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24312
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_av_sigmaI/netI    0.1321
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.00
_reflns_number_total             4929
_reflns_number_gt                2388
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms (except H1) were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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)+(0.0444P)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         4929
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0600
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.0979
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_restrained_S_all      0.980
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.14365(8) 0.37164(19) 0.21783(10) 0.0186(5) Uani 1 1 d . . .
O1 O 0.28127(7) 0.57102(17) 0.33862(9) 0.0269(5) Uani 1 1 d . . .
O2 O 0.41996(8) 0.36756(19) 0.21308(10) 0.0293(5) Uani 1 1 d . . .
N2 N 0.31622(9) 0.4448(2) 0.17363(10) 0.0210(5) Uani 1 1 d . . .
C1 C 0.13548(11) 0.4451(2) 0.27564(13) 0.0181(6) Uani 1 1 d . . .
C2 C 0.08127(11) 0.4519(3) 0.29342(14) 0.0256(6) Uani 1 1 d . . .
H2 H 0.0490 0.4085 0.2648 0.031 Uiso 1 1 calc R . .
C3 C 0.07482(12) 0.5205(3) 0.35166(14) 0.0284(7) Uani 1 1 d . . .
H3 H 0.0383 0.5224 0.3635 0.034 Uiso 1 1 calc R . .
C4 C 0.12085(12) 0.5874(3) 0.39370(14) 0.0287(7) Uani 1 1 d . . .
H4 H 0.1159 0.6353 0.4338 0.034 Uiso 1 1 calc R . .
C5 C 0.17345(11) 0.5832(2) 0.37649(13) 0.0245(6) Uani 1 1 d . . .
H5 H 0.2049 0.6299 0.4049 0.029 Uiso 1 1 calc R . .
C6 C 0.18217(10) 0.5121(2) 0.31832(12) 0.0171(6) Uani 1 1 d . . .
C7 C 0.24002(11) 0.5061(2) 0.30365(13) 0.0193(6) Uani 1 1 d . . .
C8 C 0.24506(11) 0.4189(2) 0.24676(13) 0.0176(6) Uani 1 1 d . . .
C9 C 0.19757(11) 0.3585(2) 0.20698(13) 0.0201(6) Uani 1 1 d . . .
H9 H 0.2027 0.3036 0.1692 0.024 Uiso 1 1 calc R . .
C10 C 0.09420(11) 0.3044(2) 0.17134(12) 0.0197(6) Uani 1 1 d . . .
H10 H 0.0606 0.3669 0.1673 0.024 Uiso 1 1 calc R . .
C11 C 0.07791(11) 0.1717(2) 0.20236(13) 0.0242(6) Uani 1 1 d . . .
H11A H 0.1087 0.1037 0.2036 0.029 Uiso 1 1 calc R . .
H11B H 0.0737 0.1875 0.2506 0.029 Uiso 1 1 calc R . .
C12 C 0.02146(11) 0.1177(3) 0.15858(14) 0.0291(7) Uani 1 1 d . . .
H12A H 0.0119 0.0303 0.1781 0.035 Uiso 1 1 calc R . .
H12B H -0.0099 0.1828 0.1603 0.035 Uiso 1 1 calc R . .
C13 C 0.02593(12) 0.0972(3) 0.08364(15) 0.0369(8) Uani 1 1 d . . .
H13A H -0.0121 0.0697 0.0556 0.044 Uiso 1 1 calc R . .
H13B H 0.0535 0.0230 0.0814 0.044 Uiso 1 1 calc R . .
C14 C 0.04574(12) 0.2259(3) 0.05280(14) 0.0359(8) Uani 1 1 d . . .
H14A H 0.0156 0.2965 0.0491 0.043 Uiso 1 1 calc R . .
H14B H 0.0512 0.2065 0.0054 0.043 Uiso 1 1 calc R . .
C15 C 0.10237(11) 0.2798(3) 0.09769(13) 0.0275(7) Uani 1 1 d . . .
H15A H 0.1335 0.2128 0.0985 0.033 Uiso 1 1 calc R . .
H15B H 0.1133 0.3656 0.0778 0.033 Uiso 1 1 calc R . .
C16 C 0.30257(11) 0.3980(2) 0.22924(13) 0.0181(6) Uani 1 1 d . . .
C17 C 0.34744(11) 0.3230(2) 0.27882(13) 0.0197(6) Uani 1 1 d . . .
C18 C 0.33470(11) 0.2602(2) 0.33755(13) 0.0240(6) Uani 1 1 d . . .
H18 H 0.2965 0.2646 0.3446 0.029 Uiso 1 1 calc R . .
C19 C 0.37590(11) 0.1922(3) 0.38528(14) 0.0277(7) Uani 1 1 d . . .
H19 H 0.3661 0.1493 0.4243 0.033 Uiso 1 1 calc R . .
C20 C 0.43209(12) 0.1869(3) 0.37581(14) 0.0294(7) Uani 1 1 d . . .
H20 H 0.4609 0.1419 0.4091 0.035 Uiso 1 1 calc R . .
C21 C 0.44614(11) 0.2465(3) 0.31866(14) 0.0278(7) Uani 1 1 d . . .
H21 H 0.4847 0.2426 0.3129 0.033 Uiso 1 1 calc R . .
C22 C 0.40442(11) 0.3125(2) 0.26908(13) 0.0215(6) Uani 1 1 d . . .
C23 C 0.27649(11) 0.5253(3) 0.12175(13) 0.0243(6) Uani 1 1 d . . .
H23 H 0.2405 0.5432 0.1385 0.029 Uiso 1 1 calc R . .
C24 C 0.30545(12) 0.6606(3) 0.11129(15) 0.0319(7) Uani 1 1 d . . .
H24A H 0.2768 0.7204 0.0817 0.038 Uiso 1 1 calc R . .
H24B H 0.3182 0.7056 0.1570 0.038 Uiso 1 1 calc R . .
C25 C 0.35687(12) 0.6447(3) 0.07795(15) 0.0389(8) Uani 1 1 d . . .
H25A H 0.3881 0.5966 0.1104 0.047 Uiso 1 1 calc R . .
H25B H 0.3713 0.7355 0.0685 0.047 Uiso 1 1 calc R . .
C26 C 0.34041(13) 0.5647(3) 0.00982(15) 0.0411(8) Uani 1 1 d . . .
H26A H 0.3124 0.6179 -0.0245 0.049 Uiso 1 1 calc R . .
H26B H 0.3751 0.5504 -0.0093 0.049 Uiso 1 1 calc R . .
C27 C 0.31459(12) 0.4296(3) 0.02096(14) 0.0373(8) Uani 1 1 d . . .
H27A H 0.3436 0.3734 0.0523 0.045 Uiso 1 1 calc R . .
H27B H 0.3032 0.3815 -0.0241 0.045 Uiso 1 1 calc R . .
C28 C 0.26183(12) 0.4481(3) 0.05284(13) 0.0320(7) Uani 1 1 d . . .
H28A H 0.2318 0.4984 0.0197 0.038 Uiso 1 1 calc R . .
H28B H 0.2461 0.3579 0.0606 0.038 Uiso 1 1 calc R . .
H1 H 0.3818(15) 0.409(3) 0.1827(17) 0.082(12) Uiso 1 1 d . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
N1 C9 1.354(3) . ?
N1 C1 1.399(3) . ?
N1 C10 1.482(3) . ?
O1 C7 1.247(3) . ?
O2 C22 1.352(3) . ?
O2 H1 1.05(3) . ?
N2 C16 1.294(3) . ?
N2 C23 1.466(3) . ?
C1 C6 1.405(3) . ?
C1 C2 1.412(3) . ?
C2 C3 1.369(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.369(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.470(3) . ?
C7 C8 1.438(3) . ?
C8 C9 1.365(3) . ?
C8 C16 1.499(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.525(3) . ?
C10 C11 1.529(3) . ?
C10 H10 1.0000 . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.517(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.525(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.538(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.479(3) . ?
C17 C18 1.403(3) . ?
C17 C22 1.416(3) . ?
C18 C19 1.377(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.394(3) . ?
C21 H21 0.9500 . ?
C23 C28 1.529(3) . ?
C23 C24 1.535(3) . ?
C23 H23 1.0000 . ?
C24 C25 1.520(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.532(4) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.502(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.534(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

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
C9 N1 C1 118.9(2) . . ?
C9 N1 C10 120.9(2) . . ?
C1 N1 C10 120.1(2) . . ?
C22 O2 H1 105.1(18) . . ?
C16 N2 C23 122.7(2) . . ?
N1 C1 C6 119.9(2) . . ?
N1 C1 C2 121.6(2) . . ?
C6 C1 C2 118.5(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 121.1(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 119.7(2) . . ?
C1 C6 C7 121.2(2) . . ?
O1 C7 C8 123.2(2) . . ?
O1 C7 C6 122.1(2) . . ?
C8 C7 C6 114.7(2) . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 C16 119.6(2) . . ?
C7 C8 C16 119.8(2) . . ?
N1 C9 C8 124.4(2) . . ?
N1 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
N1 C10 C15 114.2(2) . . ?
N1 C10 C11 111.8(2) . . ?
C15 C10 C11 109.9(2) . . ?
N1 C10 H10 106.8 . . ?
C15 C10 H10 106.8 . . ?
C11 C10 H10 106.8 . . ?
C12 C11 C10 109.9(2) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 110.9(2) . . ?
C13 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 C14 111.8(2) . . ?
C12 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C15 111.5(2) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C10 C15 C14 108.9(2) . . ?
C10 C15 H15A 109.9 . . ?
C14 C15 H15A 109.9 . . ?
C10 C15 H15B 109.9 . . ?
C14 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
N2 C16 C17 117.3(2) . . ?
N2 C16 C8 123.9(2) . . ?
C17 C16 C8 118.8(2) . . ?
C18 C17 C22 117.8(2) . . ?
C18 C17 C16 120.7(2) . . ?
C22 C17 C16 121.6(2) . . ?
C19 C18 C17 121.9(2) . . ?
C19 C18 H18 119.1 . . ?
C17 C18 H18 119.1 . . ?
C18 C19 C20 119.3(3) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
O2 C22 C21 118.6(2) . . ?
O2 C22 C17 121.5(2) . . ?
C21 C22 C17 119.9(2) . . ?
N2 C23 C28 109.8(2) . . ?
N2 C23 C24 108.8(2) . . ?
C28 C23 C24 109.5(2) . . ?
N2 C23 H23 109.6 . . ?
C28 C23 H23 109.6 . . ?
C24 C23 H23 109.6 . . ?
C25 C24 C23 113.4(2) . . ?
C25 C24 H24A 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C24 C25 C26 110.8(2) . . ?
C24 C25 H25A 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C27 C26 C25 111.2(2) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 C28 110.7(2) . . ?
C26 C27 H27A 109.5 . . ?
C28 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C28 C27 H27B 109.5 . . ?
H27A C27 H27B 108.1 . . ?
C23 C28 C27 112.0(2) . . ?
C23 C28 H28A 109.2 . . ?
C27 C28 H28A 109.2 . . ?
C23 C28 H28B 109.2 . . ?
C27 C28 H28B 109.2 . . ?
H28A C28 H28B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C1 C6 4.7(3) . . . . ?
C10 N1 C1 C6 -178.1(2) . . . . ?
C9 N1 C1 C2 -174.0(2) . . . . ?
C10 N1 C1 C2 3.2(3) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
C6 C1 C2 C3 -1.1(4) . . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C4 C5 C6 C7 -177.5(2) . . . . ?
N1 C1 C6 C5 -179.0(2) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C2 C1 C6 C7 178.5(2) . . . . ?
C5 C6 C7 O1 -5.4(4) . . . . ?
C1 C6 C7 O1 175.9(2) . . . . ?
C5 C6 C7 C8 173.9(2) . . . . ?
C1 C6 C7 C8 -4.8(3) . . . . ?
O1 C7 C8 C9 -175.0(2) . . . . ?
C6 C7 C8 C9 5.7(3) . . . . ?
O1 C7 C8 C16 2.8(4) . . . . ?
C6 C7 C8 C16 -176.5(2) . . . . ?
C1 N1 C9 C8 -3.9(3) . . . . ?
C10 N1 C9 C8 178.9(2) . . . . ?
C7 C8 C9 N1 -1.6(4) . . . . ?
C16 C8 C9 N1 -179.4(2) . . . . ?
C9 N1 C10 C15 -26.8(3) . . . . ?
C1 N1 C10 C15 156.0(2) . . . . ?
C9 N1 C10 C11 98.9(3) . . . . ?
C1 N1 C10 C11 -78.3(3) . . . . ?
N1 C10 C11 C12 171.1(2) . . . . ?
C15 C10 C11 C12 -60.9(3) . . . . ?
C10 C11 C12 C13 57.3(3) . . . . ?
C11 C12 C13 C14 -54.2(3) . . . . ?
C12 C13 C14 C15 54.4(3) . . . . ?
N1 C10 C15 C14 -173.2(2) . . . . ?
C11 C10 C15 C14 60.1(3) . . . . ?
C13 C14 C15 C10 -56.9(3) . . . . ?
C23 N2 C16 C17 -177.6(2) . . . . ?
C23 N2 C16 C8 0.6(4) . . . . ?
C9 C8 C16 N2 67.6(3) . . . . ?
C7 C8 C16 N2 -110.2(3) . . . . ?
C9 C8 C16 C17 -114.3(3) . . . . ?
C7 C8 C16 C17 67.9(3) . . . . ?
N2 C16 C17 C18 -175.0(2) . . . . ?
C8 C16 C17 C18 6.7(3) . . . . ?
N2 C16 C17 C22 5.2(3) . . . . ?
C8 C16 C17 C22 -173.1(2) . . . . ?
C22 C17 C18 C19 1.1(4) . . . . ?
C16 C17 C18 C19 -178.6(2) . . . . ?
C17 C18 C19 C20 0.9(4) . . . . ?
C18 C19 C20 C21 -1.4(4) . . . . ?
C19 C20 C21 C22 -0.3(4) . . . . ?
C20 C21 C22 O2 -178.9(2) . . . . ?
C20 C21 C22 C17 2.4(4) . . . . ?
C18 C17 C22 O2 178.5(2) . . . . ?
C16 C17 C22 O2 -1.7(4) . . . . ?
C18 C17 C22 C21 -2.8(3) . . . . ?
C16 C17 C22 C21 177.0(2) . . . . ?
C16 N2 C23 C28 -115.5(2) . . . . ?
C16 N2 C23 C24 124.6(2) . . . . ?
N2 C23 C24 C25 66.9(3) . . . . ?
C28 C23 C24 C25 -53.2(3) . . . . ?
C23 C24 C25 C26 53.8(3) . . . . ?
C24 C25 C26 C27 -55.4(3) . . . . ?
C25 C26 C27 C28 57.3(3) . . . . ?
N2 C23 C28 C27 -65.1(3) . . . . ?
C24 C23 C28 C27 54.4(3) . . . . ?
C26 C27 C28 C23 -57.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_is_sm458
_database_code_depnum_ccdc_archive 'CCDC 1016273'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 F O4'
_chemical_formula_sum            'C17 H11 F O4'
_chemical_formula_weight         298.26

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'
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'

#==============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

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                   7.7191(2)
_cell_length_b                   13.9145(3)
_cell_length_c                   12.5580(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.8630(10)
_cell_angle_gamma                90.00
_cell_volume                     1328.89(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8678
_cell_measurement_theta_min      6.105
_cell_measurement_theta_max      62.040

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9640
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15570
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3878
_reflns_number_gt                3405
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-97

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a riding model, 
 with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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)+(0.0600P)²+0.3070P] 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         3878
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.95911(9) 0.35569(5) 0.67588(7) 0.03778(18) Uani 1 1 d . . .
O1 O 0.44753(11) 0.39197(6) 0.68886(7) 0.03233(19) Uani 1 1 d . . .
O2 O 0.70547(11) 0.30302(5) 0.45919(6) 0.02717(17) Uani 1 1 d . . .
O3 O 0.62477(10) 0.11048(5) 0.69330(6) 0.02449(16) Uani 1 1 d . . .
O4 O 0.76722(11) -0.15478(5) 0.49788(7) 0.03047(18) Uani 1 1 d . . .
C1 C 0.62540(12) 0.27264(7) 0.63048(7) 0.02055(18) Uani 1 1 d . . .
C2 C 0.59914(13) 0.20532(7) 0.70324(8) 0.02312(19) Uani 1 1 d . . .
H2 H 0.5593 0.2267 0.7667 0.028 Uiso 1 1 calc R . .
C3 C 0.67992(12) 0.07765(7) 0.60087(7) 0.01948(18) Uani 1 1 d . . .
C4 C 0.70016(13) -0.02077(7) 0.59373(8) 0.02269(19) Uani 1 1 d . . .
H4 H 0.6774 -0.0621 0.6500 0.027 Uiso 1 1 calc R . .
C5 C 0.75483(13) -0.05766(7) 0.50188(8) 0.02163(19) Uani 1 1 d . . .
C6 C 0.79240(13) 0.00391(7) 0.41995(8) 0.02277(19) Uani 1 1 d . . .
H6 H 0.8328 -0.0216 0.3584 0.027 Uiso 1 1 calc R . .
C7 C 0.77002(13) 0.10155(7) 0.42970(7) 0.02163(18) Uani 1 1 d . . .
H7 H 0.7947 0.1429 0.3740 0.026 Uiso 1 1 calc R . .
C8 C 0.71167(12) 0.14130(6) 0.51996(7) 0.01864(17) Uani 1 1 d . . .
C9 C 0.68430(12) 0.24490(7) 0.53009(7) 0.01957(18) Uani 1 1 d . . .
C10 C 0.58274(13) 0.37453(7) 0.65453(8) 0.02214(19) Uani 1 1 d . . .
C11 C 0.70569(13) 0.45388(7) 0.63857(8) 0.02218(19) Uani 1 1 d . . .
C12 C 0.63692(15) 0.54665(7) 0.61758(8) 0.0269(2) Uani 1 1 d . . .
H12 H 0.5138 0.5569 0.6104 0.032 Uiso 1 1 calc R . .
C13 C 0.74725(18) 0.62359(8) 0.60724(10) 0.0345(3) Uani 1 1 d . . .
H13 H 0.6992 0.6860 0.5924 0.041 Uiso 1 1 calc R . .
C14 C 0.92759(18) 0.60967(9) 0.61855(10) 0.0380(3) Uani 1 1 d . . .
H14 H 1.0023 0.6626 0.6111 0.046 Uiso 1 1 calc R . .
C15 C 0.99962(16) 0.51885(9) 0.64063(10) 0.0338(2) Uani 1 1 d . . .
H15 H 1.1230 0.5089 0.6491 0.041 Uiso 1 1 calc R . .
C16 C 0.88679(14) 0.44321(8) 0.64993(8) 0.0265(2) Uani 1 1 d . . .
C17 C 0.82610(15) -0.19679(8) 0.40609(9) 0.0294(2) Uani 1 1 d . . .
H17A H 0.7507 -0.1749 0.3397 0.044 Uiso 1 1 calc R . .
H17B H 0.8201 -0.2670 0.4108 0.044 Uiso 1 1 calc R . .
H17C H 0.9477 -0.1772 0.4051 0.044 Uiso 1 1 calc R . .


#==============================================================================

# MOLECULAR GEOMETRY

_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
F1 C16 1.3560(13) . ?
O1 C10 1.2199(13) . ?
O2 C9 1.2342(12) . ?
O3 C2 1.3433(12) . ?
O3 C3 1.3808(11) . ?
O4 C5 1.3562(11) . ?
O4 C17 1.4340(13) . ?
C1 C2 1.3480(13) . ?
C1 C9 1.4633(12) . ?
C1 C10 1.4979(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3830(13) . ?
C3 C8 1.4007(12) . ?
C4 C5 1.3924(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.4068(13) . ?
C6 C7 1.3777(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.4030(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.4656(13) . ?
C10 C11 1.4917(14) . ?
C11 C16 1.3887(15) . ?
C11 C12 1.4034(14) . ?
C12 C13 1.3879(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3885(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.3893(19) . ?
C14 H14 0.9500 . ?
C15 C16 1.3837(15) . ?
C15 H15 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 O3 C3 118.34(7) . . ?
C5 O4 C17 118.04(8) . . ?
C2 C1 C9 120.37(9) . . ?
C2 C1 C10 117.21(8) . . ?
C9 C1 C10 122.34(8) . . ?
O3 C2 C1 125.31(9) . . ?
O3 C2 H2 117.3 . . ?
C1 C2 H2 117.3 . . ?
O3 C3 C4 115.89(8) . . ?
O3 C3 C8 121.20(8) . . ?
C4 C3 C8 122.91(8) . . ?
C3 C4 C5 118.19(9) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
O4 C5 C4 115.56(9) . . ?
O4 C5 C6 123.71(9) . . ?
C4 C5 C6 120.73(9) . . ?
C7 C6 C5 119.40(9) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 121.54(9) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C3 C8 C7 117.20(8) . . ?
C3 C8 C9 120.88(8) . . ?
C7 C8 C9 121.93(8) . . ?
O2 C9 C1 123.21(9) . . ?
O2 C9 C8 122.89(8) . . ?
C1 C9 C8 113.89(8) . . ?
O1 C10 C11 120.18(9) . . ?
O1 C10 C1 119.37(9) . . ?
C11 C10 C1 120.43(8) . . ?
C16 C11 C12 117.35(10) . . ?
C16 C11 C10 124.02(9) . . ?
C12 C11 C10 118.50(9) . . ?
C13 C12 C11 120.58(11) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.22(11) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 120.48(11) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 118.20(11) . . ?
C16 C15 H15 120.9 . . ?
C14 C15 H15 120.9 . . ?
F1 C16 C15 117.66(10) . . ?
F1 C16 C11 119.11(9) . . ?
C15 C16 C11 123.17(10) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O3 C2 C1 -1.05(15) . . . . ?
C9 C1 C2 O3 0.89(15) . . . . ?
C10 C1 C2 O3 177.75(9) . . . . ?
C2 O3 C3 C4 -178.51(9) . . . . ?
C2 O3 C3 C8 1.12(13) . . . . ?
O3 C3 C4 C5 179.73(8) . . . . ?
C8 C3 C4 C5 0.10(14) . . . . ?
C17 O4 C5 C4 -178.85(9) . . . . ?
C17 O4 C5 C6 1.58(15) . . . . ?
C3 C4 C5 O4 -178.08(9) . . . . ?
C3 C4 C5 C6 1.50(14) . . . . ?
O4 C5 C6 C7 177.76(9) . . . . ?
C4 C5 C6 C7 -1.78(15) . . . . ?
C5 C6 C7 C8 0.45(15) . . . . ?
O3 C3 C8 C7 179.02(8) . . . . ?
C4 C3 C8 C7 -1.37(14) . . . . ?
O3 C3 C8 C9 -1.08(14) . . . . ?
C4 C3 C8 C9 178.53(9) . . . . ?
C6 C7 C8 C3 1.08(14) . . . . ?
C6 C7 C8 C9 -178.82(9) . . . . ?
C2 C1 C9 O2 177.78(9) . . . . ?
C10 C1 C9 O2 1.09(15) . . . . ?
C2 C1 C9 C8 -0.73(13) . . . . ?
C10 C1 C9 C8 -177.42(8) . . . . ?
C3 C8 C9 O2 -177.68(9) . . . . ?
C7 C8 C9 O2 2.22(15) . . . . ?
C3 C8 C9 C1 0.84(13) . . . . ?
C7 C8 C9 C1 -179.26(9) . . . . ?
C2 C1 C10 O1 -43.44(13) . . . . ?
C9 C1 C10 O1 133.35(10) . . . . ?
C2 C1 C10 C11 135.49(10) . . . . ?
C9 C1 C10 C11 -47.72(13) . . . . ?
O1 C10 C11 C16 148.49(10) . . . . ?
C1 C10 C11 C16 -30.44(14) . . . . ?
O1 C10 C11 C12 -27.23(14) . . . . ?
C1 C10 C11 C12 153.84(9) . . . . ?
C16 C11 C12 C13 0.93(15) . . . . ?
C10 C11 C12 C13 176.94(9) . . . . ?
C11 C12 C13 C14 -0.57(17) . . . . ?
C12 C13 C14 C15 -0.21(18) . . . . ?
C13 C14 C15 C16 0.58(18) . . . . ?
C14 C15 C16 F1 -177.35(10) . . . . ?
C14 C15 C16 C11 -0.18(17) . . . . ?
C12 C11 C16 F1 176.56(9) . . . . ?
C10 C11 C16 F1 0.80(15) . . . . ?
C12 C11 C16 C15 -0.57(15) . . . . ?
C10 C11 C16 C15 -176.33(9) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.200
_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_is_sm4971
_database_code_depnum_ccdc_archive 'CCDC 1016274'
_audit_update_record             
;
2014-07-26 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H17 N3 O2'
_chemical_formula_sum            'C26 H17 N3 O2'
_chemical_formula_weight         403.42

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.5696(2)
_cell_length_b                   19.5048(5)
_cell_length_c                   11.9609(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.200(2)
_cell_angle_gamma                90
_cell_volume                     1919.86(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3150
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      25.97

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7060
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30523
_diffrn_reflns_av_unetI/netI     0.0926
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         30.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6102
_reflns_number_gt                3247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). Torsion angles 
 of all methyl groups were allowed to refine.
 
 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     
'w=1/[σ²(Fo²)+(0.0434P)²+0.2855P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6102
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1384
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1281
_refine_ls_wR_factor_gt          0.0983
_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

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.21660(18) 0.52967(7) 0.35599(12) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.29743(18) 0.54045(7) 0.47208(12) 0.0247(3) Uani 1 1 d . . . . .
N3 N 0.31802(17) 0.48190(7) 0.65458(12) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.16119(16) 0.25724(6) 0.62717(11) 0.0351(3) Uani 1 1 d . . . . .
O2 O 0.07703(15) 0.40523(6) 0.85381(11) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.1294(2) 0.47368(8) 0.35034(15) 0.0261(4) Uani 1 1 d . . . . .
C2 C 0.1509(2) 0.44539(8) 0.46338(14) 0.0232(4) Uani 1 1 d . . . . .
C3 C 0.1015(2) 0.38689(8) 0.51072(15) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.0310 0.3545 0.4625 0.029 Uiso 1 1 calc R U . . .
C4 C 0.1577(2) 0.37708(8) 0.62988(14) 0.0222(4) Uani 1 1 d . . . . .
C5 C 0.2655(2) 0.42589(8) 0.69847(14) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.2598(2) 0.48957(8) 0.53944(14) 0.0218(4) Uani 1 1 d . . . . .
C7 C 0.0300(3) 0.44592(9) 0.23712(15) 0.0355(5) Uani 1 1 d . . . . .
H7A H 0.0448 0.4746 0.1736 0.053 Uiso 1 1 calc R U . . .
H7B H -0.0849 0.4459 0.2357 0.053 Uiso 1 1 calc R U . . .
H7C H 0.0646 0.3989 0.2274 0.053 Uiso 1 1 calc R U . . .
C8 C 0.1186(2) 0.30767(8) 0.67136(15) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.0123(2) 0.29764(8) 0.74998(15) 0.0253(4) Uani 1 1 d . . . . .
C10 C -0.0815(2) 0.23790(9) 0.73351(16) 0.0317(4) Uani 1 1 d . . . . .
H10 H -0.0714 0.2057 0.6764 0.038 Uiso 1 1 calc R U . . .
C11 C -0.1882(2) 0.22467(10) 0.79809(18) 0.0386(5) Uani 1 1 d . . . . .
H11 H -0.2512 0.1839 0.7849 0.046 Uiso 1 1 calc R U . . .
C12 C -0.2037(2) 0.27059(11) 0.88192(18) 0.0427(5) Uani 1 1 d . . . . .
H12 H -0.2774 0.2616 0.9265 0.051 Uiso 1 1 calc R U . . .
C13 C -0.1114(2) 0.32990(11) 0.90085(17) 0.0369(5) Uani 1 1 d . . . . .
H13 H -0.1205 0.3614 0.9593 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0060(2) 0.34325(9) 0.83466(16) 0.0275(4) Uani 1 1 d . . . . .
C15 C 0.3399(2) 0.41612(8) 0.82524(14) 0.0232(4) Uani 1 1 d . . . . .
C16 C 0.2457(2) 0.40215(8) 0.89940(15) 0.0254(4) Uani 1 1 d . . . . .
C17 C 0.3119(2) 0.39222(9) 1.01729(16) 0.0322(4) Uani 1 1 d . . . . .
H17 H 0.2446 0.3815 1.0659 0.039 Uiso 1 1 calc R U . . .
C18 C 0.4777(3) 0.39821(10) 1.06315(17) 0.0371(5) Uani 1 1 d . . . . .
H18 H 0.5255 0.3911 1.1441 0.045 Uiso 1 1 calc R U . . .
C19 C 0.5749(2) 0.41445(10) 0.99194(16) 0.0354(5) Uani 1 1 d . . . . .
H19 H 0.6887 0.4198 1.0245 0.042 Uiso 1 1 calc R U . . .
C20 C 0.5070(2) 0.42298(9) 0.87364(15) 0.0285(4) Uani 1 1 d . . . . .
H20 H 0.5746 0.4336 0.8251 0.034 Uiso 1 1 calc R U . . .
C21 C 0.4002(2) 0.59856(8) 0.50311(15) 0.0230(4) Uani 1 1 d . . . . .
C22 C 0.4957(2) 0.60760(9) 0.61643(15) 0.0282(4) Uani 1 1 d . . . . .
H22 H 0.4948 0.5744 0.6744 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5928(2) 0.66566(9) 0.64451(17) 0.0319(4) Uani 1 1 d . . . . .
H23 H 0.6567 0.6726 0.7225 0.038 Uiso 1 1 calc R U . . .
C24 C 0.5976(2) 0.71343(9) 0.56032(16) 0.0315(4) Uani 1 1 d . . . . .
H24 H 0.6651 0.7528 0.5800 0.038 Uiso 1 1 calc R U . . .
C25 C 0.5034(2) 0.70358(9) 0.44737(16) 0.0313(4) Uani 1 1 d . . . . .
H25 H 0.5072 0.7362 0.3892 0.038 Uiso 1 1 calc R U . . .
C26 C 0.4036(2) 0.64682(9) 0.41794(16) 0.0272(4) Uani 1 1 d . . . . .
H26 H 0.3379 0.6408 0.3403 0.033 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.314(2) . ?
N1 N2 1.3840(19) . ?
N2 C6 1.372(2) . ?
N2 C21 1.420(2) . ?
N3 C6 1.336(2) . ?
N3 C5 1.343(2) . ?
O1 C8 1.2197(19) . ?
O2 C14 1.389(2) . ?
O2 C16 1.396(2) . ?
C1 C2 1.424(2) . ?
C1 C7 1.486(2) . ?
C2 C3 1.391(2) . ?
C2 C6 1.403(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.418(2) . ?
C4 C8 1.511(2) . ?
C5 C15 1.484(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.493(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C15 C16 1.383(2) . ?
C15 C20 1.393(2) . ?
C16 C17 1.379(2) . ?
C17 C18 1.378(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.385(2) . ?
C21 C26 1.393(2) . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.380(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 107.22(13) . . ?
C6 N2 N1 110.21(13) . . ?
C6 N2 C21 130.85(14) . . ?
N1 N2 C21 118.94(13) . . ?
C6 N3 C5 115.13(14) . . ?
C14 O2 C16 116.99(13) . . ?
N1 C1 C2 110.61(15) . . ?
N1 C1 C7 121.51(15) . . ?
C2 C1 C7 127.84(16) . . ?
C3 C2 C6 117.57(15) . . ?
C3 C2 C1 136.96(16) . . ?
C6 C2 C1 105.31(15) . . ?
C4 C3 C2 118.32(15) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C3 C4 C5 119.10(15) . . ?
C3 C4 C8 114.60(14) . . ?
C5 C4 C8 125.45(15) . . ?
N3 C5 C4 123.73(15) . . ?
N3 C5 C15 114.12(14) . . ?
C4 C5 C15 122.00(14) . . ?
N3 C6 N2 127.23(15) . . ?
N3 C6 C2 126.11(15) . . ?
N2 C6 C2 106.64(14) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 C9 118.43(15) . . ?
O1 C8 C4 117.35(15) . . ?
C9 C8 C4 123.67(15) . . ?
C14 C9 C10 117.30(16) . . ?
C14 C9 C8 126.01(15) . . ?
C10 C9 C8 116.64(16) . . ?
C11 C10 C9 121.55(18) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.03(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.72(19) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C14 C13 C12 119.91(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 O2 117.14(16) . . ?
C13 C14 C9 121.47(17) . . ?
O2 C14 C9 121.36(15) . . ?
C16 C15 C20 117.95(16) . . ?
C16 C15 C5 121.30(16) . . ?
C20 C15 C5 120.71(16) . . ?
C17 C16 C15 122.42(17) . . ?
C17 C16 O2 119.43(16) . . ?
C15 C16 O2 117.83(15) . . ?
C18 C17 C16 118.68(18) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C17 C18 C19 120.35(18) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.27(19) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C15 120.28(18) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C22 C21 C26 120.16(16) . . ?
C22 C21 N2 120.75(15) . . ?
C26 C21 N2 119.09(15) . . ?
C21 C22 C23 119.38(16) . . ?
C21 C22 H22 120.3 . . ?
C23 C22 H22 120.3 . . ?
C24 C23 C22 120.73(17) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.46(17) . . ?
C25 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C24 C25 C26 120.78(16) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 119.48(17) . . ?
C25 C26 H26 120.3 . . ?
C21 C26 H26 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C6 0.41(19) . . . . ?
C1 N1 N2 C21 -179.42(15) . . . . ?
N2 N1 C1 C2 -0.32(19) . . . . ?
N2 N1 C1 C7 -178.28(16) . . . . ?
N1 C1 C2 C3 -175.0(2) . . . . ?
C7 C1 C2 C3 2.8(3) . . . . ?
N1 C1 C2 C6 0.13(19) . . . . ?
C7 C1 C2 C6 177.92(18) . . . . ?
C6 C2 C3 C4 2.3(2) . . . . ?
C1 C2 C3 C4 177.02(19) . . . . ?
C2 C3 C4 C5 -1.4(2) . . . . ?
C2 C3 C4 C8 -171.39(15) . . . . ?
C6 N3 C5 C4 0.7(2) . . . . ?
C6 N3 C5 C15 176.29(14) . . . . ?
C3 C4 C5 N3 -0.2(3) . . . . ?
C8 C4 C5 N3 168.66(16) . . . . ?
C3 C4 C5 C15 -175.49(15) . . . . ?
C8 C4 C5 C15 -6.6(3) . . . . ?
C5 N3 C6 N2 -177.57(16) . . . . ?
C5 N3 C6 C2 0.5(2) . . . . ?
N1 N2 C6 N3 178.01(15) . . . . ?
C21 N2 C6 N3 -2.2(3) . . . . ?
N1 N2 C6 C2 -0.33(19) . . . . ?
C21 N2 C6 C2 179.48(17) . . . . ?
C3 C2 C6 N3 -2.0(3) . . . . ?
C1 C2 C6 N3 -178.23(16) . . . . ?
C3 C2 C6 N2 176.38(15) . . . . ?
C1 C2 C6 N2 0.13(18) . . . . ?
C3 C4 C8 O1 54.8(2) . . . . ?
C5 C4 C8 O1 -114.5(2) . . . . ?
C3 C4 C8 C9 -116.48(18) . . . . ?
C5 C4 C8 C9 74.2(2) . . . . ?
O1 C8 C9 C14 158.23(17) . . . . ?
C4 C8 C9 C14 -30.6(3) . . . . ?
O1 C8 C9 C10 -24.3(2) . . . . ?
C4 C8 C9 C10 146.92(16) . . . . ?
C14 C9 C10 C11 0.2(3) . . . . ?
C8 C9 C10 C11 -177.55(16) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 -0.1(3) . . . . ?
C11 C12 C13 C14 0.9(3) . . . . ?
C12 C13 C14 O2 176.84(17) . . . . ?
C12 C13 C14 C9 -1.2(3) . . . . ?
C16 O2 C14 C13 114.73(18) . . . . ?
C16 O2 C14 C9 -67.2(2) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C8 C9 C14 C13 178.14(17) . . . . ?
C10 C9 C14 O2 -177.29(15) . . . . ?
C8 C9 C14 O2 0.2(3) . . . . ?
N3 C5 C15 C16 131.61(16) . . . . ?
C4 C5 C15 C16 -52.7(2) . . . . ?
N3 C5 C15 C20 -46.3(2) . . . . ?
C4 C5 C15 C20 129.37(18) . . . . ?
C20 C15 C16 C17 -2.6(2) . . . . ?
C5 C15 C16 C17 179.36(15) . . . . ?
C20 C15 C16 O2 170.80(14) . . . . ?
C5 C15 C16 O2 -7.2(2) . . . . ?
C14 O2 C16 C17 -80.30(19) . . . . ?
C14 O2 C16 C15 106.05(17) . . . . ?
C15 C16 C17 C18 1.7(3) . . . . ?
O2 C16 C17 C18 -171.63(15) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -1.8(3) . . . . ?
C18 C19 C20 C15 0.8(3) . . . . ?
C16 C15 C20 C19 1.4(2) . . . . ?
C5 C15 C20 C19 179.36(15) . . . . ?
C6 N2 C21 C22 6.7(3) . . . . ?
N1 N2 C21 C22 -173.52(15) . . . . ?
C6 N2 C21 C26 -173.08(17) . . . . ?
N1 N2 C21 C26 6.7(2) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
N2 C21 C22 C23 -178.85(16) . . . . ?
C21 C22 C23 C24 -1.4(3) . . . . ?
C22 C23 C24 C25 0.6(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C25 C26 C21 -1.0(3) . . . . ?
C22 C21 C26 C25 0.3(3) . . . . ?
N2 C21 C26 C25 -179.97(16) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_av_sm8291
_database_code_depnum_ccdc_archive 'CCDC 1019513'
_audit_update_record             
;
2014-08-15 deposited with the CCDC.
2015-03-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 N2 O2'
_chemical_formula_sum            'C17 H12 N2 O2'
_chemical_formula_weight         276.29

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.1684(3)
_cell_length_b                   6.59440(10)
_cell_length_c                   17.0941(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.8650(10)
_cell_angle_gamma                90
_cell_volume                     1319.44(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8981
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      30.00

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7062
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'

#==============================================================================

# EXPERIMENTAL DATA

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker-Nonius Apex X8-CCD-diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17369
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.477
_diffrn_reflns_theta_max         30.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3798
_reflns_number_gt                3355
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex V7.51A'
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  SHELXL-2013

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms were positioned geometrically and refined using a 
 riding model, with C---H = 0.98 (methyl groups), 0.99Å (methylene groups), 
 1.00Å (methine groups) or 0.95 Å (aryl CH) and with Uiso(H) = 
 1.5 times Ueq(C) (methyl groups) or with Uiso(H) = 1.2 times 
 Ueq(C) (methylene  groups, aryl CH, methine groups). 
 
 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     
'w=1/[σ²(Fo²)+(0.0500P)²+0.5377P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3798
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1096
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.29742(9) 0.19179(17) 0.10491(6) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.19890(9) 0.06120(19) 0.10256(6) 0.0213(2) Uani 1 1 d . . . . .
C3 C 0.44722(10) 0.35997(18) 0.08818(7) 0.0222(2) Uani 1 1 d . . . . .
H3 H 0.5083 0.4093 0.0688 0.027 Uiso 1 1 calc R U . . .
C1 C 0.37446(10) 0.12424(18) -0.02612(7) 0.0216(2) Uani 1 1 d . . . . .
C10 C 0.19524(10) -0.13902(19) 0.07663(6) 0.0227(2) Uani 1 1 d . . . . .
C16 C 0.30728(9) -0.05423(18) -0.06792(7) 0.0208(2) Uani 1 1 d . . . . .
C11 C 0.27345(10) -0.21813(18) -0.02901(7) 0.0222(2) Uani 1 1 d . . . . .
C2 C 0.37134(9) 0.20603(17) 0.05310(6) 0.0196(2) Uani 1 1 d . . . . .
C15 C 0.28778(10) -0.0654(2) -0.15274(7) 0.0269(3) Uani 1 1 d . . . . .
H15 H 0.3088 0.0455 -0.1810 0.032 Uiso 1 1 calc R U . . .
C9 C 0.10420(12) -0.2654(2) 0.07670(8) 0.0346(3) Uani 1 1 d . . . . .
H9 H 0.1033 -0.4019 0.0587 0.042 Uiso 1 1 calc R U . . .
C14 C 0.23857(12) -0.2349(2) -0.19560(8) 0.0360(3) Uani 1 1 d . . . . .
H14 H 0.2236 -0.2381 -0.2531 0.043 Uiso 1 1 calc R U . . .
C17 C 0.47317(12) 0.5866(2) 0.20845(8) 0.0307(3) Uani 1 1 d . . . . .
H17A H 0.5446 0.6261 0.1966 0.046 Uiso 1 1 calc R U . . .
H17B H 0.4897 0.5386 0.2647 0.046 Uiso 1 1 calc R U . . .
H17C H 0.4219 0.7038 0.2011 0.046 Uiso 1 1 calc R U . . .
C6 C 0.10795(10) 0.1331(2) 0.13055(8) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.1091 0.2686 0.1497 0.036 Uiso 1 1 calc R U . . .
C13 C 0.21098(13) -0.4005(2) -0.15480(9) 0.0381(3) Uani 1 1 d . . . . .
H13 H 0.1803 -0.5196 -0.1840 0.046 Uiso 1 1 calc R U . . .
C12 C 0.22820(12) -0.3920(2) -0.07152(8) 0.0320(3) Uani 1 1 d . . . . .
H12 H 0.2091 -0.5050 -0.0434 0.038 Uiso 1 1 calc R U . . .
C7 C 0.01645(11) 0.0080(3) 0.13054(8) 0.0387(3) Uani 1 1 d . . . . .
H7 H -0.0450 0.0583 0.1493 0.046 Uiso 1 1 calc R U . . .
C8 C 0.01435(12) -0.1894(3) 0.10341(9) 0.0431(4) Uani 1 1 d . . . . .
H8 H -0.0490 -0.2740 0.1030 0.052 Uiso 1 1 calc R U . . .
O2 O 0.28962(7) -0.21492(13) 0.05463(5) 0.02319(18) Uani 1 1 d . . . . .
O1 O 0.43614(9) 0.20936(15) -0.06207(6) 0.0349(2) Uani 1 1 d . . . . .
N1 N 0.41890(8) 0.42545(15) 0.15354(6) 0.0225(2) Uani 1 1 d . . . . .
N2 N 0.32661(8) 0.32759(15) 0.16530(6) 0.0220(2) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C4 N2 1.3391(15) . ?
C4 C2 1.4276(15) . ?
C4 C5 1.4676(15) . ?
C5 C10 1.3896(17) . ?
C5 C6 1.4029(16) . ?
C3 N1 1.3281(15) . ?
C3 C2 1.3927(16) . ?
C3 H3 0.9500 . ?
C1 O1 1.2280(14) . ?
C1 C2 1.4678(15) . ?
C1 C16 1.4982(16) . ?
C10 C9 1.3865(17) . ?
C10 O2 1.3953(15) . ?
C16 C11 1.3892(16) . ?
C16 C15 1.4057(15) . ?
C11 C12 1.3881(17) . ?
C11 O2 1.3890(13) . ?
C15 C14 1.3802(19) . ?
C15 H15 0.9500 . ?
C9 C8 1.388(2) . ?
C9 H9 0.9500 . ?
C14 C13 1.385(2) . ?
C14 H14 0.9500 . ?
C17 N1 1.4517(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C6 C7 1.3855(19) . ?
C6 H6 0.9500 . ?
C13 C12 1.3823(19) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
C7 C8 1.380(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N1 N2 1.3571(13) . ?

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
N2 C4 C2 110.79(10) . . ?
N2 C4 C5 117.13(10) . . ?
C2 C4 C5 132.08(10) . . ?
C10 C5 C6 118.06(11) . . ?
C10 C5 C4 121.40(10) . . ?
C6 C5 C4 120.47(11) . . ?
N1 C3 C2 107.77(10) . . ?
N1 C3 H3 126.1 . . ?
C2 C3 H3 126.1 . . ?
O1 C1 C2 117.85(10) . . ?
O1 C1 C16 116.67(10) . . ?
C2 C1 C16 125.47(10) . . ?
C9 C10 C5 121.78(12) . . ?
C9 C10 O2 120.09(12) . . ?
C5 C10 O2 118.02(10) . . ?
C11 C16 C15 117.68(11) . . ?
C11 C16 C1 125.26(10) . . ?
C15 C16 C1 116.70(10) . . ?
C12 C11 O2 118.41(11) . . ?
C12 C11 C16 121.26(11) . . ?
O2 C11 C16 120.25(10) . . ?
C3 C2 C4 103.70(10) . . ?
C3 C2 C1 118.93(10) . . ?
C4 C2 C1 136.70(10) . . ?
C14 C15 C16 121.09(12) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C10 C9 C8 118.99(14) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C15 C14 C13 120.06(12) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C6 C5 120.50(14) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C12 C13 C14 119.80(13) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C12 C11 119.97(13) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C8 C7 C6 120.18(13) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 120.47(12) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C11 O2 C10 112.80(8) . . ?
C3 N1 N2 112.68(9) . . ?
C3 N1 C17 127.24(10) . . ?
N2 N1 C17 120.06(10) . . ?
C4 N2 N1 105.05(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 C4 C5 C10 -145.01(11) . . . . ?
C2 C4 C5 C10 35.82(18) . . . . ?
N2 C4 C5 C6 31.73(15) . . . . ?
C2 C4 C5 C6 -147.45(12) . . . . ?
C6 C5 C10 C9 1.06(16) . . . . ?
C4 C5 C10 C9 177.88(11) . . . . ?
C6 C5 C10 O2 -175.24(9) . . . . ?
C4 C5 C10 O2 1.57(15) . . . . ?
O1 C1 C16 C11 150.92(12) . . . . ?
C2 C1 C16 C11 -29.86(18) . . . . ?
O1 C1 C16 C15 -22.05(16) . . . . ?
C2 C1 C16 C15 157.17(11) . . . . ?
C15 C16 C11 C12 3.75(18) . . . . ?
C1 C16 C11 C12 -169.16(11) . . . . ?
C15 C16 C11 O2 -179.43(10) . . . . ?
C1 C16 C11 O2 7.66(18) . . . . ?
N1 C3 C2 C4 0.18(12) . . . . ?
N1 C3 C2 C1 172.36(10) . . . . ?
N2 C4 C2 C3 0.52(12) . . . . ?
C5 C4 C2 C3 179.74(11) . . . . ?
N2 C4 C2 C1 -169.48(12) . . . . ?
C5 C4 C2 C1 9.7(2) . . . . ?
O1 C1 C2 C3 -7.25(17) . . . . ?
C16 C1 C2 C3 173.54(11) . . . . ?
O1 C1 C2 C4 161.63(13) . . . . ?
C16 C1 C2 C4 -17.6(2) . . . . ?
C11 C16 C15 C14 -1.12(18) . . . . ?
C1 C16 C15 C14 172.40(12) . . . . ?
C5 C10 C9 C8 0.01(18) . . . . ?
O2 C10 C9 C8 176.24(11) . . . . ?
C16 C15 C14 C13 -2.2(2) . . . . ?
C10 C5 C6 C7 -1.28(17) . . . . ?
C4 C5 C6 C7 -178.13(11) . . . . ?
C15 C14 C13 C12 2.9(2) . . . . ?
C14 C13 C12 C11 -0.3(2) . . . . ?
O2 C11 C12 C13 -179.99(12) . . . . ?
C16 C11 C12 C13 -3.1(2) . . . . ?
C5 C6 C7 C8 0.4(2) . . . . ?
C6 C7 C8 C9 0.7(2) . . . . ?
C10 C9 C8 C7 -0.9(2) . . . . ?
C12 C11 O2 C10 -91.07(13) . . . . ?
C16 C11 O2 C10 92.03(12) . . . . ?
C9 C10 O2 C11 83.45(13) . . . . ?
C5 C10 O2 C11 -100.18(11) . . . . ?
C2 C3 N1 N2 -0.84(13) . . . . ?
C2 C3 N1 C17 -179.05(11) . . . . ?
C2 C4 N2 N1 -0.99(12) . . . . ?
C5 C4 N2 N1 179.66(9) . . . . ?
C3 N1 N2 C4 1.14(13) . . . . ?
C17 N1 N2 C4 179.50(10) . . . . ?

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.067

_shelxl_version_number           2013-4



