# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wdh1022
_audit_creation_date             2014-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C25 H26 N2 O2), 0.5(C2 H8 O2)'
_chemical_formula_sum            'C51 H56 N4 O5'
_chemical_formula_weight         805.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H10 N2 O3'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.4413(9)
_cell_length_b                   10.7973(6)
_cell_length_c                   18.1182(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.275(5)
_cell_angle_gamma                90.00
_cell_volume                     4289.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3426
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.6850
_cell_measurement_theta_min      3.3480
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1720
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8361
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.97
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00   25.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   38.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  2 omega  -80.00   34.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000  -60.0000 114

#__ type_ start__ end____ width___ exp.time_
  3 omega   63.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  178.0000  150.0000 31
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0125376000
_diffrn_orient_matrix_UB_12      0.0300207000
_diffrn_orient_matrix_UB_13      0.0280315000
_diffrn_orient_matrix_UB_21      -0.0133350000
_diffrn_orient_matrix_UB_22      0.0453398000
_diffrn_orient_matrix_UB_23      -0.0267471000
_diffrn_orient_matrix_UB_31      -0.0267027000
_diffrn_orient_matrix_UB_32      -0.0368165000
_diffrn_orient_matrix_UB_33      -0.0101123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_number_gt                3602
_reflns_number_total             4392
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0357P)²+4.5957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1125
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O3-C27
 1.414 with sigma of 0.002
3. Others
 Fixed Sof: O3(0.5) H3A(0.5) H27A(0.5) H27B(0.5) H27C(0.5)
 Fixed X: H3A(0.4885) H27A(0.4878) H27B(0.548301) H27C(0.48829)
 Fixed Y: H3A(0.3069) H27A(0.1808) H27B(0.1965) H27C(0.114429)
 Fixed Z: H3A(0.665501) H27A(0.7997) H27B(0.763) H27C(0.72086)
4.a Ternary CH refined with riding coordinates:
 C19(H19)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
4.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C21(H21), C22(H22),
 C24(H24), C25(H25)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C26(H26A,H26B,
 H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.57554(5) 0.98012(10) 0.42319(7) 0.0250(3) Uani 1 d . . 1 . . .
O2 O 0.47681(5) 0.66754(12) 0.42515(7) 0.0284(3) Uani 1 d . . 1 . . .
N1 N 0.58354(6) 0.79180(12) 0.48383(8) 0.0206(3) Uani 1 d . . 1 . . .
N2 N 0.42123(6) 0.80773(13) 0.47568(8) 0.0218(3) Uani 1 d . . 1 . . .
H2 H 0.4238 0.8685 0.5069 0.026 Uiso 1 calc . . 1 R . .
C1 C 0.69173(7) 0.88028(15) 0.36758(8) 0.0186(3) Uani 1 d . . 1 . . .
C2 C 0.68224(7) 1.00023(16) 0.33582(9) 0.0243(4) Uani 1 d . . 1 . . .
H2A H 0.6497 1.0479 0.3438 0.029 Uiso 1 calc . . 1 R . .
C3 C 0.72097(8) 1.04634(17) 0.29334(9) 0.0270(4) Uani 1 d . . 1 . . .
H3 H 0.7137 1.1243 0.2715 0.032 Uiso 1 calc . . 1 R . .
C4 C 0.77149(7) 0.97717(17) 0.28246(9) 0.0257(4) Uani 1 d . . 1 . . .
H4 H 0.7978 1.0103 0.2544 0.031 Uiso 1 calc . . 1 R . .
C5 C 0.78207(7) 0.86141(16) 0.31299(9) 0.0221(4) Uani 1 d . . 1 . . .
H5 H 0.8157 0.8165 0.3057 0.027 Uiso 1 calc . . 1 R . .
C6 C 0.74217(7) 0.80912(15) 0.35569(8) 0.0191(3) Uani 1 d . . 1 . . .
C7 C 0.75174(7) 0.68818(15) 0.38685(9) 0.0208(3) Uani 1 d . . 1 . . .
H7 H 0.7848 0.6422 0.3788 0.025 Uiso 1 calc . . 1 R . .
C8 C 0.71365(7) 0.63762(15) 0.42839(9) 0.0203(3) Uani 1 d . . 1 . . .
H8 H 0.7203 0.5581 0.4481 0.024 Uiso 1 calc . . 1 R . .
C9 C 0.66415(7) 0.70870(15) 0.44067(8) 0.0180(3) Uani 1 d . . 1 . . .
C10 C 0.65369(7) 0.82611(15) 0.41203(8) 0.0176(3) Uani 1 d . . 1 . . .
C11 C 0.61803(7) 0.67664(15) 0.48651(9) 0.0195(3) Uani 1 d . . 1 . . .
H11A H 0.5922 0.6087 0.4640 0.023 Uiso 1 calc . . 1 R . .
H11B H 0.6375 0.6550 0.5379 0.023 Uiso 1 calc . . 1 R . .
C12 C 0.60039(7) 0.87839(15) 0.43788(9) 0.0196(3) Uani 1 d . . 1 . . .
C14 C 0.47334(7) 0.75393(15) 0.46780(9) 0.0195(3) Uani 1 d . . 1 . . .
C15 C 0.35930(7) 0.77012(16) 0.43450(10) 0.0240(4) Uani 1 d . . 1 . . .
C16 C 0.35453(9) 0.7842(2) 0.34959(11) 0.0390(5) Uani 1 d . . 1 . . .
H16A H 0.3636 0.8682 0.3384 0.058 Uiso 1 calc . . 1 GR . .
H16B H 0.3139 0.7638 0.3233 0.058 Uiso 1 calc . . 1 GR . .
H16C H 0.3831 0.7295 0.3337 0.058 Uiso 1 calc . . 1 GR . .
C17 C 0.31452(8) 0.85703(19) 0.46031(14) 0.0426(5) Uani 1 d . . 1 . . .
H17A H 0.3178 0.8480 0.5137 0.064 Uiso 1 calc . . 1 GR . .
H17B H 0.2738 0.8371 0.4343 0.064 Uiso 1 calc . . 1 GR . .
H17C H 0.3237 0.9410 0.4492 0.064 Uiso 1 calc . . 1 GR . .
C18 C 0.34691(7) 0.63689(16) 0.45452(9) 0.0241(4) Uani 1 d . . 1 . . .
H18A H 0.3749 0.5826 0.4371 0.036 Uiso 1 calc . . 1 GR . .
H18B H 0.3059 0.6149 0.4308 0.036 Uiso 1 calc . . 1 GR . .
H18C H 0.3522 0.6293 0.5083 0.036 Uiso 1 calc . . 1 GR . .
C19 C 0.53105(7) 0.80858(15) 0.51886(9) 0.0203(3) Uani 1 d . . 1 . . .
H19 H 0.5245 0.8978 0.5233 0.024 Uiso 1 calc . . 1 R . .
C20 C 0.54333(7) 0.75404(16) 0.59774(9) 0.0215(4) Uani 1 d . . 1 . . .
C21 C 0.55652(7) 0.83228(19) 0.66034(10) 0.0321(4) Uani 1 d . . 1 . . .
H21 H 0.5554 0.9177 0.6536 0.039 Uiso 1 calc . . 1 R . .
C22 C 0.57123(8) 0.7833(2) 0.73240(10) 0.0402(6) Uani 1 d . . 1 . . .
H22 H 0.5792 0.8367 0.7736 0.048 Uiso 1 calc . . 1 R . .
C23 C 0.57440(7) 0.6567(2) 0.74469(10) 0.0362(5) Uani 1 d . . 1 . . .
C24 C 0.55910(7) 0.5789(2) 0.68248(9) 0.0295(4) Uani 1 d . . 1 . . .
H24 H 0.5595 0.4936 0.6895 0.035 Uiso 1 calc . . 1 R . .
C25 C 0.54320(7) 0.62720(16) 0.61000(9) 0.0220(4) Uani 1 d . . 1 . . .
H25 H 0.5323 0.5738 0.5691 0.026 Uiso 1 calc . . 1 R . .
C26 C 0.59477(9) 0.6043(3) 0.82330(10) 0.0577(8) Uani 1 d . . 1 . . .
H26A H 0.5792 0.5217 0.8247 0.087 Uiso 1 calc . . 1 GR . .
H26B H 0.5795 0.6553 0.8586 0.087 Uiso 1 calc . . 1 GR . .
H26C H 0.6385 0.6025 0.8367 0.087 Uiso 1 calc . . 1 GR . .
O3 O 0.47442(15) 0.3008(3) 0.71089(17) 0.0572(9) Uani 0.50 d . 1 1 D . .
H3A H 0.4885 0.3069 0.6655 0.086 Uiso 0.50 d A 1 1 R . .
C27 C 0.5000 0.1943(3) 0.7500 0.0599(10) Uani 1 d . 1 2 DS T P
H27A H 0.4878 0.1808 0.7997 0.090 Uiso 0.50 d B 1 1 R . .
H27B H 0.5483 0.1965 0.7630 0.090 Uiso 0.50 d C 1 1 R . .
H27C H 0.4883 0.1144 0.7209 0.090 Uiso 0.50 d D 1 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.2351(19) . ?
O2 C14 1.2243(19) . ?
N1 C11 1.460(2) . ?
N1 C12 1.358(2) . ?
N1 C19 1.4632(19) . ?
N2 H2 0.8600 . ?
N2 C14 1.340(2) . ?
N2 C15 1.487(2) . ?
C1 C2 1.415(2) . ?
C1 C6 1.422(2) . ?
C1 C10 1.418(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.371(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.406(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.419(2) . ?
C6 C7 1.421(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.367(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.406(2) . ?
C9 C10 1.371(2) . ?
C9 C11 1.499(2) . ?
C10 C12 1.485(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C14 C19 1.540(2) . ?
C15 C16 1.527(2) . ?
C15 C17 1.520(2) . ?
C15 C18 1.524(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9800 . ?
C19 C20 1.516(2) . ?
C20 C21 1.395(2) . ?
C20 C25 1.388(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.382(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(3) . ?
C23 C24 1.389(3) . ?
C23 C26 1.510(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(2) . ?
C25 H25 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
O3 O3 1.623(6) 2_656 ?
O3 H3A 0.944(3) . ?
O3 C27 1.4077(19) . ?
C27 O3 1.4077(19) 2_656 ?
C27 H27A 1.0059(5) . ?
C27 H27B 1.0594 . ?
C27 H27C 1.016(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C19 124.13(13) . . ?
C12 N1 C11 113.07(12) . . ?
C12 N1 C19 122.38(13) . . ?
C14 N2 H2 117.6 . . ?
C14 N2 C15 124.86(14) . . ?
C15 N2 H2 117.6 . . ?
C2 C1 C6 119.27(14) . . ?
C2 C1 C10 123.48(14) . . ?
C10 C1 C6 117.25(14) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 C1 120.14(16) . . ?
C3 C2 H2A 119.9 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.81(17) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.30(16) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.60(15) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.85(15) . . ?
C5 C6 C7 121.51(15) . . ?
C7 C6 C1 119.63(14) . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.76(15) . . ?
C8 C7 H7 119.1 . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.46(15) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 C11 128.57(15) . . ?
C10 C9 C8 121.48(14) . . ?
C10 C9 C11 109.90(13) . . ?
C1 C10 C12 130.13(14) . . ?
C9 C10 C1 121.39(14) . . ?
C9 C10 C12 108.46(13) . . ?
N1 C11 C9 102.04(12) . . ?
N1 C11 H11A 111.4 . . ?
N1 C11 H11B 111.4 . . ?
C9 C11 H11A 111.4 . . ?
C9 C11 H11B 111.4 . . ?
H11A C11 H11B 109.2 . . ?
O1 C12 N1 124.92(14) . . ?
O1 C12 C10 128.83(15) . . ?
N1 C12 C10 106.23(13) . . ?
O2 C14 N2 124.87(15) . . ?
O2 C14 C19 120.84(14) . . ?
N2 C14 C19 114.28(14) . . ?
N2 C15 C16 109.64(14) . . ?
N2 C15 C17 106.59(14) . . ?
N2 C15 C18 109.68(13) . . ?
C17 C15 C16 109.84(16) . . ?
C17 C15 C18 110.10(15) . . ?
C18 C15 C16 110.90(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 C14 110.11(13) . . ?
N1 C19 H19 107.8 . . ?
N1 C19 C20 111.05(12) . . ?
C14 C19 H19 107.8 . . ?
C20 C19 C14 112.24(13) . . ?
C20 C19 H19 107.8 . . ?
C21 C20 C19 119.74(16) . . ?
C25 C20 C19 121.88(14) . . ?
C25 C20 C21 118.36(16) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 C20 120.23(19) . . ?
C22 C21 H21 119.9 . . ?
C21 C22 H22 119.2 . . ?
C21 C22 C23 121.56(17) . . ?
C23 C22 H22 119.2 . . ?
C22 C23 C24 118.10(18) . . ?
C22 C23 C26 121.1(2) . . ?
C24 C23 C26 120.8(2) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.72(19) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.89(16) . . ?
C24 C25 H25 119.6 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 O3 H3A 117.1(4) 2_656 . ?
C27 O3 O3 54.80(16) . 2_656 ?
C27 O3 H3A 108.6(2) . . ?
O3 C27 O3 70.4(3) . 2_656 ?
O3 C27 H27A 80.06(18) 2_656 . ?
O3 C27 H27A 114.2(2) . . ?
O3 C27 H27B 112.5(3) . . ?
O3 C27 H27B 65.25(18) 2_656 . ?
O3 C27 H27C 171.01(15) 2_656 . ?
O3 C27 H27C 113.53(14) . . ?
H27A C27 H27B 105.34(3) . . ?
H27A C27 H27C 104.6(3) . . ?
H27B C27 H27C 105.9(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
O2 C14 C19 N1 28.3(2) . . . . ?
O2 C14 C19 C20 -95.91(17) . . . . ?
N1 C19 C20 C21 104.17(16) . . . . ?
N1 C19 C20 C25 -74.40(18) . . . . ?
N2 C14 C19 N1 -152.54(14) . . . . ?
N2 C14 C19 C20 83.20(17) . . . . ?
C1 C2 C3 C4 -1.8(2) . . . . ?
C1 C6 C7 C8 -0.1(2) . . . . ?
C1 C10 C12 O1 3.7(3) . . . . ?
C1 C10 C12 N1 -175.17(15) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C7 -179.48(14) . . . . ?
C2 C1 C10 C9 178.97(15) . . . . ?
C2 C1 C10 C12 -3.1(3) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C4 C5 C6 C1 -1.4(2) . . . . ?
C4 C5 C6 C7 178.94(15) . . . . ?
C5 C6 C7 C8 179.62(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C1 C10 C9 -1.7(2) . . . . ?
C6 C1 C10 C12 176.23(15) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C11 -177.14(15) . . . . ?
C8 C9 C10 C1 1.1(2) . . . . ?
C8 C9 C10 C12 -177.19(14) . . . . ?
C8 C9 C11 N1 174.02(15) . . . . ?
C9 C10 C12 O1 -178.19(16) . . . . ?
C9 C10 C12 N1 2.98(17) . . . . ?
C10 C1 C2 C3 -179.93(15) . . . . ?
C10 C1 C6 C5 -178.54(14) . . . . ?
C10 C1 C6 C7 1.2(2) . . . . ?
C10 C9 C11 N1 -3.39(17) . . . . ?
C11 N1 C12 O1 175.70(15) . . . . ?
C11 N1 C12 C10 -5.41(17) . . . . ?
C11 N1 C19 C14 -80.60(18) . . . . ?
C11 N1 C19 C20 44.4(2) . . . . ?
C11 C9 C10 C1 178.77(14) . . . . ?
C11 C9 C10 C12 0.44(17) . . . . ?
C12 N1 C11 C9 5.51(17) . . . . ?
C12 N1 C19 C14 91.42(18) . . . . ?
C12 N1 C19 C20 -143.63(15) . . . . ?
C14 N2 C15 C16 -60.5(2) . . . . ?
C14 N2 C15 C17 -179.35(16) . . . . ?
C14 N2 C15 C18 61.5(2) . . . . ?
C14 C19 C20 C21 -132.09(15) . . . . ?
C14 C19 C20 C25 49.33(19) . . . . ?
C15 N2 C14 O2 0.7(3) . . . . ?
C15 N2 C14 C19 -178.34(14) . . . . ?
C19 N1 C11 C9 178.18(13) . . . . ?
C19 N1 C12 O1 2.9(2) . . . . ?
C19 N1 C12 C10 -178.23(13) . . . . ?
C19 C20 C21 C22 -176.26(14) . . . . ?
C19 C20 C25 C24 175.04(13) . . . . ?
C20 C21 C22 C23 1.1(3) . . . . ?
C21 C20 C25 C24 -3.6(2) . . . . ?
C21 C22 C23 C24 -3.4(3) . . . . ?
C21 C22 C23 C26 175.71(15) . . . . ?
C22 C23 C24 C25 2.2(2) . . . . ?
C23 C24 C25 C20 1.3(2) . . . . ?
C25 C20 C21 C22 2.4(2) . . . . ?
C26 C23 C24 C25 -176.92(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009249'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wdh1023
_audit_creation_date             2014-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2942 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H24 N2 O2'
_chemical_formula_sum            'C24 H24 N2 O2'
_chemical_formula_weight         372.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H10 N2 O3'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7602(4)
_cell_length_b                   10.7729(7)
_cell_length_c                   12.2413(7)
_cell_angle_alpha                65.145(6)
_cell_angle_beta                 88.691(4)
_cell_angle_gamma                83.815(4)
_cell_volume                     1041.81(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3783
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.1780
_cell_measurement_theta_min      3.2990
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7439
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.937
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -6.00   84.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   70.0000 -146.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00   45.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -70.0000   82.0000 95

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   22.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  -30.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   33.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  -57.0000  -30.0000 46

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701   38.0000    0.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0573979000
_diffrn_orient_matrix_UB_12      -0.0267676000
_diffrn_orient_matrix_UB_13      0.0428447000
_diffrn_orient_matrix_UB_21      -0.0152995000
_diffrn_orient_matrix_UB_22      -0.0444874000
_diffrn_orient_matrix_UB_23      -0.0267850000
_diffrn_orient_matrix_UB_31      0.0557535000
_diffrn_orient_matrix_UB_32      -0.0513034000
_diffrn_orient_matrix_UB_33      0.0390808000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3535
_reflns_number_total             4256
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         4256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0325P)²+0.5514P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1050
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C19(H19), C8(H8), C16(H16), C15(H15), C18(H18), C17(H17), C4(H4),
 C7(H7), C2(H2A), C3(H3), C5(H5)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.16217(12) 1.05439(10) 0.83413(9) 0.0184(2) Uani 1 1 d . . . . .
O2 O 0.15337(12) 0.64189(11) 1.02185(9) 0.0200(2) Uani 1 1 d . . . . .
C C 0.06825(16) 0.72608(15) 1.04478(12) 0.0158(3) Uani 1 1 d . . . . .
C10 C 0.18593(17) 0.98304(15) 0.66766(12) 0.0164(3) Uani 1 1 d . . . . .
N2 N 0.05231(15) 0.72731(13) 1.15355(11) 0.0189(3) Uani 1 1 d . . . . .
H2 H -0.0099 0.7943 1.1587 0.023 Uiso 1 1 calc R . . . .
C1 C 0.27691(17) 1.07606(15) 0.57950(13) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.13222(16) 0.98053(14) 0.78425(12) 0.0150(3) Uani 1 1 d . . . . .
C14 C -0.19614(17) 0.80583(15) 0.94389(12) 0.0159(3) Uani 1 1 d . . . . .
C6 C 0.29784(18) 1.05939(16) 0.47011(13) 0.0208(3) Uani 1 1 d . . . . .
C13 C -0.03415(16) 0.84309(15) 0.94554(12) 0.0151(3) Uani 1 1 d . . . . .
H13 H -0.0410 0.9256 0.9638 0.018 Uiso 1 1 calc R . . . .
C19 C -0.22372(18) 0.67406(16) 0.95925(13) 0.0200(3) Uani 1 1 d . . . . .
H19 H -0.1400 0.6050 0.9731 0.024 Uiso 1 1 calc R . . . .
C12 C 0.03169(18) 0.80130(15) 0.75610(13) 0.0178(3) Uani 1 1 d . . . . .
H12A H -0.0750 0.8014 0.7310 0.021 Uiso 1 1 calc R . . . .
H12B H 0.0782 0.7051 0.8002 0.021 Uiso 1 1 calc R . . . .
C8 C 0.14836(18) 0.86214(16) 0.54327(13) 0.0211(3) Uani 1 1 d . . . . .
H8 H 0.1072 0.7898 0.5326 0.025 Uiso 1 1 calc R . . . .
C20 C 0.13152(19) 0.62427(16) 1.26557(13) 0.0211(3) Uani 1 1 d . . . . .
C16 C -0.47009(18) 0.87449(18) 0.92141(14) 0.0247(4) Uani 1 1 d . . . . .
H16 H -0.5543 0.9428 0.9088 0.030 Uiso 1 1 calc R . . . .
C15 C -0.32068(18) 0.90547(16) 0.92512(13) 0.0204(3) Uani 1 1 d . . . . .
H15 H -0.3033 0.9952 0.9148 0.025 Uiso 1 1 calc R . . . .
C18 C -0.37270(19) 0.64377(17) 0.95441(14) 0.0246(4) Uani 1 1 d . . . . .
H18 H -0.3905 0.5545 0.9637 0.029 Uiso 1 1 calc R . . . .
C17 C -0.49594(18) 0.74348(18) 0.93609(14) 0.0254(4) Uani 1 1 d . . . . .
H17 H -0.5979 0.7221 0.9336 0.030 Uiso 1 1 calc R . . . .
C4 C 0.45070(19) 1.25151(17) 0.39455(14) 0.0273(4) Uani 1 1 d . . . . .
H4 H 0.5083 1.3123 0.3320 0.033 Uiso 1 1 calc R . . . .
C23 C 0.08619(19) 0.48112(16) 1.29267(14) 0.0245(4) Uani 1 1 d . . . . .
H23A H 0.1238 0.4535 1.2293 0.037 Uiso 1 1 calc GR . . . .
H23B H -0.0259 0.4833 1.2956 0.037 Uiso 1 1 calc GR . . . .
H23C H 0.1317 0.4149 1.3705 0.037 Uiso 1 1 calc GR . . . .
C21 C 0.3052(2) 0.62731(18) 1.25347(15) 0.0292(4) Uani 1 1 d . . . . .
H21A H 0.3307 0.7206 1.2340 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.3397 0.6003 1.1891 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.3566 0.5630 1.3296 0.044 Uiso 1 1 calc GR . . . .
C22 C 0.0767(2) 0.66743(19) 1.36527(14) 0.0346(4) Uani 1 1 d . . . . .
H22A H -0.0348 0.6660 1.3723 0.052 Uiso 1 1 calc GR . . . .
H22B H 0.1026 0.7606 1.3456 0.052 Uiso 1 1 calc GR . . . .
H22C H 0.1272 0.6033 1.4419 0.052 Uiso 1 1 calc GR . . . .
N1 N 0.03714(14) 0.87949(12) 0.82873(10) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.12556(17) 0.88002(15) 0.65035(13) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.23165(18) 0.95210(17) 0.45504(13) 0.0223(3) Uani 1 1 d . . . . .
H7 H 0.2458 0.9428 0.3816 0.027 Uiso 1 1 calc R . . . .
C2 C 0.34764(18) 1.18039(16) 0.59482(14) 0.0217(3) Uani 1 1 d . . . . .
H2A H 0.3358 1.1915 0.6676 0.026 Uiso 1 1 calc R . . . .
C3 C 0.43342(19) 1.26549(17) 0.50394(14) 0.0254(4) Uani 1 1 d . . . . .
H3 H 0.4816 1.3345 0.5150 0.030 Uiso 1 1 calc R . . . .
C5 C 0.38503(18) 1.15106(17) 0.37822(14) 0.0241(4) Uani 1 1 d . . . . .
H5 H 0.3979 1.1424 0.3044 0.029 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2391(18) . ?
O2 C 1.2313(18) . ?
C N2 1.3411(19) . ?
C C13 1.5454(19) . ?
C10 C1 1.424(2) . ?
C10 C11 1.483(2) . ?
C10 C9 1.373(2) . ?
N2 H2 0.8800 . ?
N2 C20 1.4805(18) . ?
C1 C6 1.429(2) . ?
C1 C2 1.420(2) . ?
C11 N1 1.3607(19) . ?
C14 C13 1.519(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.395(2) . ?
C6 C7 1.426(2) . ?
C6 C5 1.419(2) . ?
C13 H13 1.0000 . ?
C13 N1 1.4591(18) . ?
C19 H19 0.9500 . ?
C19 C18 1.387(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 N1 1.4636(18) . ?
C12 C9 1.500(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.410(2) . ?
C8 C7 1.369(2) . ?
C20 C23 1.530(2) . ?
C20 C21 1.528(2) . ?
C20 C22 1.529(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.391(2) . ?
C16 C17 1.389(2) . ?
C15 H15 0.9500 . ?
C18 H18 0.9500 . ?
C18 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C4 H4 0.9500 . ?
C4 C3 1.412(2) . ?
C4 C5 1.365(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C7 H7 0.9500 . ?
C2 H2A 0.9500 . ?
C2 C3 1.377(2) . ?
C3 H3 0.9500 . ?
C5 H5 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
O2 C N2 125.58(13) . . ?
O2 C C13 121.10(13) . . ?
N2 C C13 113.32(12) . . ?
C1 C10 C11 129.55(14) . . ?
C9 C10 C1 121.92(13) . . ?
C9 C10 C11 108.44(13) . . ?
C N2 H2 117.6 . . ?
C N2 C20 124.87(13) . . ?
C20 N2 H2 117.6 . . ?
C10 C1 C6 116.38(14) . . ?
C2 C1 C10 124.28(14) . . ?
C2 C1 C6 119.34(14) . . ?
O1 C11 C10 129.06(14) . . ?
O1 C11 N1 124.70(13) . . ?
N1 C11 C10 106.23(12) . . ?
C19 C14 C13 121.53(13) . . ?
C15 C14 C13 119.48(13) . . ?
C15 C14 C19 118.99(14) . . ?
C7 C6 C1 119.96(14) . . ?
C5 C6 C1 118.72(15) . . ?
C5 C6 C7 121.32(14) . . ?
C C13 H13 107.7 . . ?
C14 C13 C 111.80(12) . . ?
C14 C13 H13 107.7 . . ?
N1 C13 C 110.03(11) . . ?
N1 C13 C14 111.65(11) . . ?
N1 C13 H13 107.7 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.33(15) . . ?
C18 C19 H19 119.8 . . ?
H12A C12 H12B 109.3 . . ?
N1 C12 H12A 111.4 . . ?
N1 C12 H12B 111.4 . . ?
N1 C12 C9 101.68(12) . . ?
C9 C12 H12A 111.4 . . ?
C9 C12 H12B 111.4 . . ?
C9 C8 H8 121.0 . . ?
C7 C8 H8 121.0 . . ?
C7 C8 C9 118.04(15) . . ?
N2 C20 C23 109.93(13) . . ?
N2 C20 C21 109.90(13) . . ?
N2 C20 C22 105.88(13) . . ?
C21 C20 C23 111.17(14) . . ?
C21 C20 C22 109.76(14) . . ?
C22 C20 C23 110.06(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C17 C16 C15 119.89(15) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.58(15) . . ?
C16 C15 H15 119.7 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C17 120.26(16) . . ?
C17 C18 H18 119.9 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.95(15) . . ?
C18 C17 H17 120.0 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.35(15) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 N1 C13 122.10(12) . . ?
C11 N1 C12 113.18(12) . . ?
C13 N1 C12 124.22(12) . . ?
C10 C9 C12 110.11(13) . . ?
C10 C9 C8 121.68(14) . . ?
C8 C9 C12 128.15(14) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.98(14) . . ?
C8 C7 H7 119.0 . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.88(15) . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 H3 119.6 . . ?
C2 C3 C4 120.81(16) . . ?
C2 C3 H3 119.6 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.86(15) . . ?
C4 C5 H5 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 C11 N1 C13 -3.3(2) . . . . ?
O1 C11 N1 C12 -175.53(13) . . . . ?
O2 C N2 C20 -2.0(2) . . . . ?
O2 C C13 C14 96.16(16) . . . . ?
O2 C C13 N1 -28.51(19) . . . . ?
C N2 C20 C23 -60.68(19) . . . . ?
C N2 C20 C21 61.99(19) . . . . ?
C N2 C20 C22 -179.53(15) . . . . ?
C C13 N1 C11 -91.90(15) . . . . ?
C C13 N1 C12 79.47(16) . . . . ?
C10 C1 C6 C7 -1.2(2) . . . . ?
C10 C1 C6 C5 178.79(13) . . . . ?
C10 C1 C2 C3 -179.92(14) . . . . ?
C10 C11 N1 C13 177.73(12) . . . . ?
C10 C11 N1 C12 5.49(16) . . . . ?
N2 C C13 C14 -83.33(15) . . . . ?
N2 C C13 N1 152.00(12) . . . . ?
C1 C10 C11 O1 -4.7(3) . . . . ?
C1 C10 C11 N1 174.24(14) . . . . ?
C1 C10 C9 C12 -178.38(13) . . . . ?
C1 C10 C9 C8 -1.1(2) . . . . ?
C1 C6 C7 C8 -0.5(2) . . . . ?
C1 C6 C5 C4 1.4(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C11 C10 C1 C6 -174.22(14) . . . . ?
C11 C10 C1 C2 6.6(2) . . . . ?
C11 C10 C9 C12 -1.42(16) . . . . ?
C11 C10 C9 C8 175.90(13) . . . . ?
C14 C13 N1 C11 143.35(13) . . . . ?
C14 C13 N1 C12 -45.28(18) . . . . ?
C14 C19 C18 C17 -1.0(2) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C13 C N2 C20 177.47(13) . . . . ?
C13 C14 C19 C18 -178.41(13) . . . . ?
C13 C14 C15 C16 179.03(13) . . . . ?
C19 C14 C13 C -41.09(18) . . . . ?
C19 C14 C13 N1 82.67(16) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C19 C18 C17 C16 0.6(2) . . . . ?
C15 C14 C13 C 139.73(13) . . . . ?
C15 C14 C13 N1 -96.51(15) . . . . ?
C15 C14 C19 C18 0.8(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C17 C16 C15 C14 -0.2(2) . . . . ?
N1 C12 C9 C10 4.36(16) . . . . ?
N1 C12 C9 C8 -172.74(14) . . . . ?
C9 C10 C1 C6 2.0(2) . . . . ?
C9 C10 C1 C2 -177.11(14) . . . . ?
C9 C10 C11 O1 178.68(14) . . . . ?
C9 C10 C11 N1 -2.40(16) . . . . ?
C9 C12 N1 C11 -6.12(16) . . . . ?
C9 C12 N1 C13 -178.17(12) . . . . ?
C9 C8 C7 C6 1.6(2) . . . . ?
C7 C6 C5 C4 -178.56(15) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C7 C8 C9 C12 176.01(15) . . . . ?
C2 C1 C6 C7 177.95(14) . . . . ?
C2 C1 C6 C5 -2.0(2) . . . . ?
C3 C4 C5 C6 0.3(2) . . . . ?
C5 C6 C7 C8 179.43(14) . . . . ?
C5 C4 C3 C2 -1.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009250'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wdh1024
_audit_creation_date             2014-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.18 svn.r2945 for OlexSys, GUI svn.r4846)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C25 H25 F N2 O2), 0.5(C2 H4 Cl4)'
_chemical_formula_sum            'C51 H52 Cl2 F2 N4 O4'
_chemical_formula_weight         893.87
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H10 N2 O3 F'
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'
Cl Cl 0.1484 0.1585 '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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.2842(10)
_cell_length_b                   11.1478(5)
_cell_length_c                   18.7003(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.746(5)
_cell_angle_gamma                90.00
_cell_volume                     4531.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3240
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.9870
_cell_measurement_theta_min      3.3100
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63950
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9553
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -10.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   56.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   19.0000   90.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega   57.00   92.00   1.0000   45.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8701  178.0000   30.0000 35
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0019096000
_diffrn_orient_matrix_UB_12      -0.0288464000
_diffrn_orient_matrix_UB_13      0.0342037000
_diffrn_orient_matrix_UB_21      0.0217735000
_diffrn_orient_matrix_UB_22      0.0432605000
_diffrn_orient_matrix_UB_23      0.0171967000
_diffrn_orient_matrix_UB_31      -0.0242760000
_diffrn_orient_matrix_UB_32      0.0366581000
_diffrn_orient_matrix_UB_33      0.0066097000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_number_gt                3619
_reflns_number_total             4641
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.960
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0523P)²+6.0441P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1392
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H12A,H12B} of C12, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H26A,H26B} of C26
2. Restrained distances
 C26-H26A = C26-H26B
 1.08 with sigma of 0.02
 H26A-H26B
 1.592 with sigma of 0.02
 Cl1-H26A = Cl1-H26B = Cl2-H26A = Cl2-H26B
 2.257 with sigma of 0.02
3. Rigid bond restraints
 Cl2, Cl1, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(Cl1) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(Cl2) \\sim Ueq: with sigma of
0.1 and sigma for terminal atoms of 0.2
5. Others
 Fixed Sof: C26(0.5) H26A(0.5) H26B(0.5) Cl1(0.5)
6.a Ternary CH refined with riding coordinates:
 C13(H13)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C8(H8), C2(H2A), C15(H15), C7(H7), C16(H16), C4(H4), C19(H19),
  C18(H18)
6.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C25(H25A,H25B,
 H25C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O1 O 0.57884(6) 0.02414(13) 0.43799(8) 0.0338(4) Uani 1 d . . 1 . . .
N2 N 0.41939(7) 0.19330(15) 0.47370(10) 0.0299(4) Uani 1 d . . 1 . . .
H2 H 0.4220 0.1286 0.5012 0.036 Uiso 1 calc . . 1 R . .
F1 F 0.71310(6) -0.15025(13) 0.28296(9) 0.0544(4) Uani 1 d . . 1 . . .
C1 C 0.69067(8) 0.12392(18) 0.37717(10) 0.0252(4) Uani 1 d . . 1 . . .
N1 N 0.58201(7) 0.21302(15) 0.48812(10) 0.0268(4) Uani 1 d . . 1 . . .
C5 C 0.77875(9) 0.1438(2) 0.31963(11) 0.0311(5) Uani 1 d . . 1 . . .
H5 H 0.8119 0.1897 0.3098 0.037 Uiso 1 calc . . 1 R . .
C10 C 0.65313(8) 0.17759(18) 0.42034(11) 0.0247(4) Uani 1 d . . 1 . . .
C9 C 0.66196(8) 0.29386(17) 0.44437(11) 0.0251(4) Uani 1 d . . 1 . . .
C11 C 0.60106(8) 0.12598(18) 0.44770(11) 0.0256(4) Uani 1 d . . 1 . . .
C6 C 0.73934(9) 0.19465(19) 0.36167(11) 0.0272(4) Uani 1 d . . 1 . . .
C13 C 0.52921(9) 0.19722(18) 0.52194(11) 0.0269(4) Uani 1 d . . 1 . . .
H13 H 0.5219 0.1091 0.5252 0.032 Uiso 1 calc . . 1 R . .
C8 C 0.70974(9) 0.36434(19) 0.42863(12) 0.0294(5) Uani 1 d . . 1 . . .
H8 H 0.7157 0.4446 0.4457 0.035 Uiso 1 calc . . 1 R . .
O2 O 0.47477(7) 0.34242(16) 0.43673(10) 0.0479(5) Uani 1 d . . 1 . . .
C14 C 0.54243(8) 0.24667(19) 0.59885(11) 0.0279(4) Uani 1 d . . 1 . . .
C2 C 0.68178(9) 0.0055(2) 0.34984(12) 0.0326(5) Uani 1 d . . 1 . . .
H2A H 0.6496 -0.0433 0.3597 0.039 Uiso 1 calc . . 1 R . .
C15 C 0.54407(9) 0.3693(2) 0.61294(12) 0.0298(5) Uani 1 d . . 1 . . .
H15 H 0.5333 0.4247 0.5736 0.036 Uiso 1 calc . . 1 R . .
C12 C 0.61554(9) 0.32580(17) 0.48832(12) 0.0266(4) Uani 1 d . . 1 . . .
H12A H 0.6357 0.3503 0.5388 0.032 Uiso 1 calc . . 1 R . .
H12B H 0.5880 0.3910 0.4647 0.032 Uiso 1 calc . . 1 R . .
C3 C 0.72075(9) -0.0361(2) 0.30903(13) 0.0366(5) Uani 1 d . . 1 . . .
C7 C 0.74740(9) 0.31449(19) 0.38815(12) 0.0308(5) Uani 1 d . . 1 . . .
H7 H 0.7799 0.3613 0.3774 0.037 Uiso 1 calc . . 1 R . .
C21 C 0.47148(9) 0.25219(19) 0.47272(11) 0.0280(4) Uani 1 d . . 1 . . .
C22 C 0.35767(9) 0.2293(2) 0.43176(13) 0.0339(5) Uani 1 d . . 1 . . .
C16 C 0.56150(9) 0.4105(2) 0.68445(13) 0.0402(6) Uani 1 d . . 1 . . .
H16 H 0.5632 0.4944 0.6936 0.048 Uiso 1 calc . . 1 R . .
C4 C 0.76950(9) 0.0298(2) 0.29324(12) 0.0349(5) Uani 1 d . . 1 . . .
H4 H 0.7956 -0.0040 0.2647 0.042 Uiso 1 calc . . 1 R . .
C19 C 0.55574(9) 0.1673(2) 0.65769(13) 0.0378(5) Uani 1 d . . 1 . . .
H19 H 0.5537 0.0834 0.6489 0.045 Uiso 1 calc . . 1 R . .
C18 C 0.57175(10) 0.2094(3) 0.72814(14) 0.0466(7) Uani 1 d . . 1 . . .
H18 H 0.5798 0.1539 0.7676 0.056 Uiso 1 calc . . 1 R . .
C17 C 0.57651(9) 0.3312(3) 0.74306(13) 0.0469(7) Uani 1 d . . 1 . . .
C24 C 0.34174(11) 0.3529(2) 0.45649(13) 0.0415(6) Uani 1 d . . 1 . . .
H24A H 0.3463 0.3532 0.5098 0.062 Uiso 1 calc . . 1 GR . .
H24B H 0.2992 0.3727 0.4327 0.062 Uiso 1 calc . . 1 GR . .
H24C H 0.3695 0.4126 0.4428 0.062 Uiso 1 calc . . 1 GR . .
C23 C 0.35680(12) 0.2285(3) 0.35025(14) 0.0520(7) Uani 1 d . . 1 . . .
H23A H 0.3858 0.2886 0.3398 0.078 Uiso 1 calc . . 1 GR . .
H23B H 0.3153 0.2475 0.3224 0.078 Uiso 1 calc . . 1 GR . .
H23C H 0.3688 0.1489 0.3360 0.078 Uiso 1 calc . . 1 GR . .
C20 C 0.59830(12) 0.3757(4) 0.82055(14) 0.0715(11) Uani 1 d . . 1 . . .
H20A H 0.5867 0.4601 0.8233 0.107 Uiso 1 calc . . 1 GR . .
H20B H 0.6431 0.3680 0.8353 0.107 Uiso 1 calc . . 1 GR . .
H20C H 0.5792 0.3279 0.8535 0.107 Uiso 1 calc . . 1 GR . .
C25 C 0.31260(11) 0.1369(3) 0.4491(2) 0.0756(11) Uani 1 d . . 1 . . .
H25A H 0.3244 0.0568 0.4356 0.113 Uiso 1 calc . . 1 GR . .
H25B H 0.2710 0.1556 0.4212 0.113 Uiso 1 calc . . 1 GR . .
H25C H 0.3133 0.1388 0.5017 0.113 Uiso 1 calc . . 1 GR . .
C26 C 0.5136(2) 0.7635(6) 0.7739(3) 0.0559(14) Uani 0.50 d . . 1 D U .
H26A H 0.5563(7) 0.745(2) 0.7671(19) 0.084 Uiso 0.50 d . . 1 DR . .
H26B H 0.5091(15) 0.747(2) 0.8241(8) 0.084 Uiso 0.50 d . . 1 DR . .
Cl1 Cl 0.45926(10) 0.68472(14) 0.71014(8) 0.0718(5) Uani 0.50 d . . 1 D U .
Cl2 Cl 0.5000 0.91571(12) 0.7500 0.1169(6) Uani 1 d . . 2 DS TU P


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.236(2) . ?
N2 H2 0.8800 . ?
N2 C21 1.337(3) . ?
N2 C22 1.480(3) . ?
F1 C3 1.360(3) . ?
C1 C10 1.417(3) . ?
C1 C6 1.421(3) . ?
C1 C2 1.413(3) . ?
N1 C11 1.354(3) . ?
N1 C13 1.464(2) . ?
N1 C12 1.462(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.420(3) . ?
C5 C4 1.362(3) . ?
C10 C9 1.372(3) . ?
C10 C11 1.484(3) . ?
C9 C8 1.406(3) . ?
C9 C12 1.499(3) . ?
C6 C7 1.422(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.507(3) . ?
C13 C21 1.535(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.366(3) . ?
O2 C21 1.221(3) . ?
C14 C15 1.391(3) . ?
C14 C19 1.391(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.358(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C3 C4 1.396(3) . ?
C7 H7 0.9500 . ?
C22 C24 1.521(3) . ?
C22 C23 1.520(3) . ?
C22 C25 1.522(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.390(4) . ?
C4 H4 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.370(4) . ?
C18 H18 0.9500 . ?
C18 C17 1.385(4) . ?
C17 C20 1.507(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C26 0.963(10) 2_656 ?
C26 H26A 1.009(16) . ?
C26 H26B 0.983(15) . ?
C26 Cl1 1.738(6) . ?
C26 Cl1 1.071(6) 2_656 ?
C26 Cl2 1.764(7) . ?
Cl1 C26 1.071(6) 2_656 ?
Cl1 Cl1 2.080(4) 2_656 ?
Cl2 C26 1.764(7) 2_656 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 N2 H2 117.7 . . ?
C21 N2 C22 124.58(18) . . ?
C22 N2 H2 117.7 . . ?
C10 C1 C6 117.06(18) . . ?
C2 C1 C10 123.16(18) . . ?
C2 C1 C6 119.78(18) . . ?
C11 N1 C13 122.38(16) . . ?
C11 N1 C12 113.24(15) . . ?
C12 N1 C13 124.14(16) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(2) . . ?
C1 C10 C11 129.63(18) . . ?
C9 C10 C1 121.71(18) . . ?
C9 C10 C11 108.66(17) . . ?
C10 C9 C8 121.34(18) . . ?
C10 C9 C12 109.73(16) . . ?
C8 C9 C12 128.92(18) . . ?
O1 C11 N1 125.12(18) . . ?
O1 C11 C10 128.61(18) . . ?
N1 C11 C10 106.26(16) . . ?
C1 C6 C7 119.57(18) . . ?
C5 C6 C1 118.98(19) . . ?
C5 C6 C7 121.45(18) . . ?
N1 C13 H13 107.6 . . ?
N1 C13 C14 111.20(16) . . ?
N1 C13 C21 109.89(16) . . ?
C14 C13 H13 107.6 . . ?
C14 C13 C21 112.81(16) . . ?
C21 C13 H13 107.6 . . ?
C9 C8 H8 120.8 . . ?
C7 C8 C9 118.36(19) . . ?
C7 C8 H8 120.8 . . ?
C15 C14 C13 122.10(18) . . ?
C19 C14 C13 119.0(2) . . ?
C19 C14 C15 118.9(2) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 C1 117.8(2) . . ?
C3 C2 H2A 121.1 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.1 . . ?
N1 C12 C9 102.03(15) . . ?
N1 C12 H12A 111.4 . . ?
N1 C12 H12B 111.4 . . ?
C9 C12 H12A 111.4 . . ?
C9 C12 H12B 111.4 . . ?
H12A C12 H12B 109.2 . . ?
F1 C3 C4 117.30(19) . . ?
C2 C3 F1 118.4(2) . . ?
C2 C3 C4 124.2(2) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 C6 121.95(18) . . ?
C8 C7 H7 119.0 . . ?
N2 C21 C13 114.27(18) . . ?
O2 C21 N2 124.7(2) . . ?
O2 C21 C13 120.99(17) . . ?
N2 C22 C24 109.65(18) . . ?
N2 C22 C23 109.54(18) . . ?
N2 C22 C25 106.47(19) . . ?
C24 C22 C25 109.8(2) . . ?
C23 C22 C24 111.0(2) . . ?
C23 C22 C25 110.3(2) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.2(2) . . ?
C17 C16 H16 119.4 . . ?
C5 C4 C3 118.5(2) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C14 C19 H19 119.7 . . ?
C18 C19 C14 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C19 C18 H18 119.3 . . ?
C19 C18 C17 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C16 C17 C20 121.3(3) . . ?
C18 C17 C16 118.0(2) . . ?
C18 C17 C20 120.7(3) . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 C26 H26A 107(2) 2_656 . ?
C26 C26 H26B 135(2) 2_656 . ?
C26 C26 Cl1 33.2(3) 2_656 . ?
C26 C26 Cl1 117.3(5) 2_656 2_656 ?
C26 C26 Cl2 74.16(18) 2_656 . ?
H26A C26 H26B 112.4(18) . . ?
Cl1 C26 H26A 51.5(16) 2_656 . ?
Cl1 C26 H26A 110.1(16) . . ?
Cl1 C26 H26B 110.9(16) . . ?
Cl1 C26 H26B 75.4(19) 2_656 . ?
Cl1 C26 Cl1 92.4(5) 2_656 . ?
Cl1 C26 Cl2 104.9(3) . . ?
Cl1 C26 Cl2 156.1(5) 2_656 . ?
Cl2 C26 H26A 106.1(16) . . ?
Cl2 C26 H26B 112.2(17) . . ?
C26 Cl1 C26 29.5(4) 2_656 . ?
C26 Cl1 Cl1 56.6(3) 2_656 2_656 ?
C26 Cl1 Cl1 31.0(2) . 2_656 ?
C26 Cl2 C26 31.7(4) 2_656 . ?

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
F1 C3 C4 C5 -179.03(19) . . . . ?
C1 C10 C9 C8 -1.5(3) . . . . ?
C1 C10 C9 C12 179.83(18) . . . . ?
C1 C10 C11 O1 -0.6(4) . . . . ?
C1 C10 C11 N1 178.20(19) . . . . ?
C1 C6 C7 C8 0.3(3) . . . . ?
C1 C2 C3 F1 179.38(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
N1 C13 C14 C15 73.9(2) . . . . ?
N1 C13 C14 C19 -103.6(2) . . . . ?
N1 C13 C21 N2 145.67(18) . . . . ?
N1 C13 C21 O2 -34.6(3) . . . . ?
C5 C6 C7 C8 180.0(2) . . . . ?
C10 C1 C6 C5 178.96(18) . . . . ?
C10 C1 C6 C7 -1.3(3) . . . . ?
C10 C1 C2 C3 179.98(19) . . . . ?
C10 C9 C8 C7 0.4(3) . . . . ?
C10 C9 C12 N1 2.1(2) . . . . ?
C9 C10 C11 O1 179.9(2) . . . . ?
C9 C10 C11 N1 -1.3(2) . . . . ?
C9 C8 C7 C6 0.2(3) . . . . ?
C11 N1 C13 C14 137.60(19) . . . . ?
C11 N1 C13 C21 -96.8(2) . . . . ?
C11 N1 C12 C9 -3.1(2) . . . . ?
C11 C10 C9 C8 177.99(18) . . . . ?
C11 C10 C9 C12 -0.7(2) . . . . ?
C6 C1 C10 C9 2.0(3) . . . . ?
C6 C1 C10 C11 -177.44(19) . . . . ?
C6 C1 C2 C3 -0.2(3) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C13 N1 C11 O1 -3.8(3) . . . . ?
C13 N1 C11 C10 177.35(17) . . . . ?
C13 N1 C12 C9 -177.54(17) . . . . ?
C13 C14 C15 C16 -174.57(17) . . . . ?
C13 C14 C19 C18 175.88(18) . . . . ?
C8 C9 C12 N1 -176.4(2) . . . . ?
C14 C13 C21 N2 -89.6(2) . . . . ?
C14 C13 C21 O2 90.1(2) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C14 C19 C18 C17 -1.4(3) . . . . ?
C2 C1 C10 C9 -178.21(19) . . . . ?
C2 C1 C10 C11 2.4(3) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
C2 C1 C6 C7 178.84(19) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C15 C14 C19 C18 -1.7(3) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C15 C16 C17 C20 177.14(19) . . . . ?
C12 N1 C11 O1 -178.35(19) . . . . ?
C12 N1 C11 C10 2.8(2) . . . . ?
C12 N1 C13 C14 -48.4(3) . . . . ?
C12 N1 C13 C21 77.2(2) . . . . ?
C12 C9 C8 C7 178.7(2) . . . . ?
C21 N2 C22 C24 -61.5(3) . . . . ?
C21 N2 C22 C23 60.5(3) . . . . ?
C21 N2 C22 C25 179.8(2) . . . . ?
C21 C13 C14 C15 -50.1(2) . . . . ?
C21 C13 C14 C19 132.45(18) . . . . ?
C22 N2 C21 C13 179.19(18) . . . . ?
C22 N2 C21 O2 -0.6(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 C7 -178.5(2) . . . . ?
C19 C14 C15 C16 2.9(3) . . . . ?
C19 C18 C17 C16 3.2(3) . . . . ?
C19 C18 C17 C20 -175.9(2) . . . . ?
C26 C26 Cl1 Cl1 140.8(13) 2_656 . . 2_656 ?
Cl1 C26 Cl1 C26 -140.8(13) 2_656 . . 2_656 ?
Cl1 C26 Cl2 C26 -12.6(4) . . . 2_656 ?
Cl1 C26 Cl2 C26 122.5(17) 2_656 . . 2_656 ?
Cl2 C26 Cl1 C26 22.5(7) . . . 2_656 ?
Cl2 C26 Cl1 Cl1 163.3(6) . . . 2_656 ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009251'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_wdh1025
_audit_creation_date             2014-06-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2942 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2012-9
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H26 N2 O2'
_chemical_formula_sum            'C25 H26 N2 O2'
_chemical_formula_weight         386.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H10 N2 O3 F'
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.9848(9)
_cell_length_b                   13.5350(10)
_cell_length_c                   13.8969(10)
_cell_angle_alpha                87.087(6)
_cell_angle_beta                 72.785(6)
_cell_angle_gamma                80.922(6)
_cell_volume                     2126.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6381
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.0040
_cell_measurement_theta_min      3.0560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85415
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0378
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16637
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.954
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 15.9631
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   13.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   58.0000  -91.0000 52

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000   30.0000 32

#__ type_ start__ end____ width___ exp.time_
  3 omega  -33.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513   57.0000   30.0000 80

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   24.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  -90.0000 37

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   22.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -99.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  -54.00   47.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513    0.0000 -180.0000 101

#__ type_ start__ end____ width___ exp.time_
  7 omega  -70.00    0.00   1.0000   18.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1513  -57.0000  120.0000 70
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0339019000
_diffrn_orient_matrix_UB_12      -0.0346384000
_diffrn_orient_matrix_UB_13      0.0242310000
_diffrn_orient_matrix_UB_21      -0.0526774000
_diffrn_orient_matrix_UB_22      -0.0116731000
_diffrn_orient_matrix_UB_23      0.0351341000
_diffrn_orient_matrix_UB_31      -0.0016060000
_diffrn_orient_matrix_UB_32      -0.0384756000
_diffrn_orient_matrix_UB_33      -0.0321514000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6908
_reflns_number_total             8666
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         8666
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0347P)²+1.0885P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1127
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C38(H38)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C36(H36A,H36B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4A), C2(H2A), C3(H3), C4(H4), C5(H5), C7(H7), C10(H10), C15(H15),
 C16(H16), C19(H19), C20(H20), C27(H27), C28(H28), C29(H29), C30(H30), C32(H32),
  C35(H35), C40(H40), C41(H41), C43(H43), C44(H44)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C45(H45A,H45B,H45C), C48(H48A,H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,
 H50B,H50C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.46154(9) 0.04137(9) 0.38863(9) 0.0295(3) Uani 1 1 d . . . . .
O2 O 0.12820(9) 0.01483(8) 0.65836(9) 0.0261(3) Uani 1 1 d . . . . .
O3 O 0.63605(10) 0.52216(8) 0.88067(9) 0.0295(3) Uani 1 1 d . . . . .
O4 O 0.33532(14) 0.77278(9) 0.91574(10) 0.0445(4) Uani 1 1 d . . . . .
N1 N 0.28115(11) -0.01068(10) 0.45842(10) 0.0216(3) Uani 1 1 d . . . . .
N2 N 0.29338(11) -0.00601(9) 0.71029(10) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.3687 -0.0316 0.6930 0.027 Uiso 1 1 calc R . . . .
N3 N 0.49236(11) 0.60813(10) 0.81655(10) 0.0222(3) Uani 1 1 d . . . . .
N4 N 0.32228(12) 0.68414(10) 1.06027(10) 0.0250(3) Uani 1 1 d . . . . .
H4A H 0.3329 0.6233 1.0848 0.030 Uiso 1 1 calc R . . . .
C1 C 0.27076(14) 0.16672(12) 0.16801(13) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.30686(17) 0.22980(13) 0.08401(13) 0.0314(4) Uani 1 1 d . . . . .
H2A H 0.3850 0.2456 0.0647 0.038 Uiso 1 1 calc R . . . .
C3 C 0.23171(18) 0.26835(14) 0.03031(14) 0.0364(4) Uani 1 1 d . . . . .
H3 H 0.2569 0.3115 -0.0254 0.044 Uiso 1 1 calc R . . . .
C4 C 0.11649(17) 0.24405(14) 0.05752(14) 0.0371(5) Uani 1 1 d . . . . .
H4 H 0.0645 0.2703 0.0193 0.045 Uiso 1 1 calc R . . . .
C5 C 0.07845(16) 0.18331(14) 0.13795(14) 0.0339(4) Uani 1 1 d . . . . .
H5 H 0.0005 0.1675 0.1548 0.041 Uiso 1 1 calc R . . . .
C6 C 0.15346(14) 0.14333(12) 0.19692(13) 0.0264(4) Uani 1 1 d . . . . .
C7 C 0.11347(14) 0.08372(12) 0.28313(13) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.0358 0.0671 0.3017 0.031 Uiso 1 1 calc R . . . .
C8 C 0.18813(13) 0.05050(11) 0.33908(12) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.30347(13) 0.07440(11) 0.31011(12) 0.0218(3) Uani 1 1 d . . . . .
C10 C 0.34619(14) 0.12989(12) 0.22654(12) 0.0244(4) Uani 1 1 d . . . . .
H10 H 0.4252 0.1434 0.2082 0.029 Uiso 1 1 calc R . . . .
C11 C 0.36071(13) 0.03463(12) 0.38689(12) 0.0228(3) Uani 1 1 d . . . . .
C12 C 0.16855(13) -0.00794(12) 0.43579(13) 0.0242(4) Uani 1 1 d . . . . .
H12A H 0.1017 0.0264 0.4896 0.029 Uiso 1 1 calc R . . . .
H12B H 0.1533 -0.0762 0.4268 0.029 Uiso 1 1 calc R . . . .
C13 C 0.31153(13) -0.06136(11) 0.54406(12) 0.0212(3) Uani 1 1 d . . . . .
H13 H 0.3949 -0.0528 0.5374 0.025 Uiso 1 1 calc R . . . .
C14 C 0.30875(13) -0.17294(12) 0.54270(12) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.38084(16) -0.22712(13) 0.45874(14) 0.0332(4) Uani 1 1 d . . . . .
H15 H 0.4290 -0.1938 0.4040 0.040 Uiso 1 1 calc R . . . .
C16 C 0.38269(19) -0.32897(14) 0.45461(15) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.4324 -0.3647 0.3967 0.048 Uiso 1 1 calc R . . . .
C17 C 0.31412(18) -0.38033(13) 0.53259(15) 0.0360(5) Uani 1 1 d . . . . .
C18 C 0.3140(2) -0.49077(14) 0.52482(18) 0.0560(7) Uani 1 1 d . . . . .
H18A H 0.2679 -0.5158 0.5894 0.084 Uiso 1 1 calc GR . . . .
H18B H 0.3954 -0.5258 0.5079 0.084 Uiso 1 1 calc GR . . . .
H18C H 0.2787 -0.5027 0.4720 0.084 Uiso 1 1 calc GR . . . .
C19 C 0.24430(16) -0.32653(12) 0.61648(14) 0.0309(4) Uani 1 1 d . . . . .
H19 H 0.1975 -0.3603 0.6717 0.037 Uiso 1 1 calc R . . . .
C20 C 0.24133(14) -0.22401(12) 0.62143(13) 0.0259(4) Uani 1 1 d . . . . .
H20 H 0.1922 -0.1885 0.6798 0.031 Uiso 1 1 calc R . . . .
C21 C 0.23473(13) -0.01276(11) 0.64354(12) 0.0211(3) Uani 1 1 d . . . . .
C22 C 0.24290(15) 0.04063(12) 0.81065(13) 0.0263(4) Uani 1 1 d . . . . .
C23 C 0.20109(19) 0.15105(13) 0.79639(14) 0.0392(5) Uani 1 1 d . . . . .
H23A H 0.2674 0.1824 0.7543 0.059 Uiso 1 1 calc GR . . . .
H23B H 0.1706 0.1840 0.8622 0.059 Uiso 1 1 calc GR . . . .
H23C H 0.1383 0.1579 0.7636 0.059 Uiso 1 1 calc GR . . . .
C24 C 0.34269(16) 0.02845(13) 0.85938(14) 0.0334(4) Uani 1 1 d . . . . .
H24A H 0.3685 -0.0429 0.8685 0.050 Uiso 1 1 calc GR . . . .
H24B H 0.3146 0.0617 0.9250 0.050 Uiso 1 1 calc GR . . . .
H24C H 0.4092 0.0587 0.8159 0.050 Uiso 1 1 calc GR . . . .
C25 C 0.14233(16) -0.01087(14) 0.87505(14) 0.0356(4) Uani 1 1 d . . . . .
H25A H 0.0771 -0.0008 0.8449 0.053 Uiso 1 1 calc GR . . . .
H25B H 0.1149 0.0176 0.9430 0.053 Uiso 1 1 calc GR . . . .
H25C H 0.1700 -0.0826 0.8789 0.053 Uiso 1 1 calc GR . . . .
C26 C 0.85364(15) 0.65397(12) 0.59873(13) 0.0268(4) Uani 1 1 d . . . . .
C27 C 0.97721(16) 0.65228(15) 0.56210(15) 0.0382(5) Uani 1 1 d . . . . .
H27 H 1.0269 0.6135 0.5964 0.046 Uiso 1 1 calc R . . . .
C28 C 1.02623(17) 0.70514(15) 0.47870(15) 0.0390(5) Uani 1 1 d . . . . .
H28 H 1.1095 0.7033 0.4557 0.047 Uiso 1 1 calc R . . . .
C29 C 0.95459(16) 0.76237(13) 0.42640(14) 0.0315(4) Uani 1 1 d . . . . .
H29 H 0.9893 0.7994 0.3683 0.038 Uiso 1 1 calc R . . . .
C30 C 0.83527(15) 0.76484(12) 0.45889(13) 0.0267(4) Uani 1 1 d . . . . .
H30 H 0.7877 0.8034 0.4225 0.032 Uiso 1 1 calc R . . . .
C31 C 0.78074(14) 0.71144(11) 0.54531(12) 0.0228(3) Uani 1 1 d . . . . .
C32 C 0.65623(14) 0.71710(11) 0.58165(12) 0.0218(3) Uani 1 1 d . . . . .
H32 H 0.6070 0.7542 0.5459 0.026 Uiso 1 1 calc R . . . .
C33 C 0.60858(14) 0.66841(11) 0.66856(12) 0.0205(3) Uani 1 1 d . . . . .
C34 C 0.68101(14) 0.61184(11) 0.72101(12) 0.0226(3) Uani 1 1 d . . . . .
C35 C 0.80077(15) 0.60329(12) 0.68762(13) 0.0276(4) Uani 1 1 d . . . . .
H35 H 0.8481 0.5638 0.7236 0.033 Uiso 1 1 calc R . . . .
C36 C 0.48185(14) 0.66660(12) 0.72706(12) 0.0232(3) Uani 1 1 d . . . . .
H36A H 0.4393 0.7350 0.7454 0.028 Uiso 1 1 calc R . . . .
H36B H 0.4406 0.6335 0.6886 0.028 Uiso 1 1 calc R . . . .
C37 C 0.60564(14) 0.57365(11) 0.81479(12) 0.0231(3) Uani 1 1 d . . . . .
C38 C 0.39276(14) 0.59421(11) 0.90331(12) 0.0226(3) Uani 1 1 d . . . . .
H38 H 0.4229 0.5447 0.9491 0.027 Uiso 1 1 calc R . . . .
C39 C 0.29888(14) 0.55051(11) 0.87319(12) 0.0237(3) Uani 1 1 d . . . . .
C40 C 0.33264(16) 0.46695(12) 0.81179(13) 0.0293(4) Uani 1 1 d . . . . .
H40 H 0.4140 0.4400 0.7875 0.035 Uiso 1 1 calc R . . . .
C41 C 0.25018(17) 0.42221(13) 0.78524(14) 0.0332(4) Uani 1 1 d . . . . .
H41 H 0.2758 0.3650 0.7430 0.040 Uiso 1 1 calc R . . . .
C42 C 0.13120(17) 0.45913(13) 0.81900(15) 0.0351(4) Uani 1 1 d . . . . .
C43 C 0.09831(17) 0.54215(14) 0.87973(18) 0.0450(5) Uani 1 1 d . . . . .
H43 H 0.0169 0.5689 0.9042 0.054 Uiso 1 1 calc R . . . .
C44 C 0.18063(16) 0.58796(14) 0.90623(16) 0.0382(5) Uani 1 1 d . . . . .
H44 H 0.1550 0.6458 0.9476 0.046 Uiso 1 1 calc R . . . .
C45 C 0.0406(2) 0.41094(15) 0.7896(2) 0.0518(6) Uani 1 1 d . . . . .
H45A H 0.0487 0.4231 0.7179 0.078 Uiso 1 1 calc GR . . . .
H45B H -0.0389 0.4397 0.8297 0.078 Uiso 1 1 calc GR . . . .
H45C H 0.0533 0.3387 0.8022 0.078 Uiso 1 1 calc GR . . . .
C46 C 0.34652(15) 0.69346(12) 0.96085(13) 0.0256(4) Uani 1 1 d . . . . .
C47 C 0.27889(15) 0.76746(13) 1.13329(13) 0.0290(4) Uani 1 1 d . . . . .
C48 C 0.36908(19) 0.83919(18) 1.11373(18) 0.0559(7) Uani 1 1 d . . . . .
H48A H 0.3804 0.8675 1.0458 0.084 Uiso 1 1 calc GR . . . .
H48B H 0.4444 0.8030 1.1195 0.084 Uiso 1 1 calc GR . . . .
H48C H 0.3405 0.8933 1.1633 0.084 Uiso 1 1 calc GR . . . .
C49 C 0.2634(2) 0.71914(16) 1.23638(15) 0.0486(6) Uani 1 1 d . . . . .
H49A H 0.2361 0.7711 1.2882 0.073 Uiso 1 1 calc GR . . . .
H49B H 0.3391 0.6817 1.2398 0.073 Uiso 1 1 calc GR . . . .
H49C H 0.2050 0.6734 1.2477 0.073 Uiso 1 1 calc GR . . . .
C50 C 0.16107(17) 0.82227(14) 1.12638(15) 0.0379(4) Uani 1 1 d . . . . .
H50A H 0.1046 0.7748 1.1370 0.057 Uiso 1 1 calc GR . . . .
H50B H 0.1713 0.8531 1.0596 0.057 Uiso 1 1 calc GR . . . .
H50C H 0.1312 0.8743 1.1781 0.057 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.2335(18) . ?
O2 C21 1.2303(18) . ?
O3 C37 1.2285(19) . ?
O4 C46 1.225(2) . ?
N1 C11 1.355(2) . ?
N1 C12 1.4683(19) . ?
N1 C13 1.454(2) . ?
N2 H2 0.8800 . ?
N2 C21 1.333(2) . ?
N2 C22 1.476(2) . ?
N3 C36 1.466(2) . ?
N3 C37 1.358(2) . ?
N3 C38 1.453(2) . ?
N4 H4A 0.8800 . ?
N4 C46 1.329(2) . ?
N4 C47 1.480(2) . ?
C1 C2 1.412(2) . ?
C1 C6 1.425(2) . ?
C1 C10 1.407(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.360(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.407(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.362(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.418(2) . ?
C6 C7 1.414(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.363(2) . ?
C8 C9 1.406(2) . ?
C8 C12 1.500(2) . ?
C9 C10 1.362(2) . ?
C9 C11 1.469(2) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C13 C14 1.517(2) . ?
C13 C21 1.529(2) . ?
C14 C15 1.391(2) . ?
C14 C20 1.380(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 C18 1.504(2) . ?
C17 C19 1.381(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C19 C20 1.387(2) . ?
C20 H20 0.9500 . ?
C22 C23 1.522(2) . ?
C22 C24 1.524(2) . ?
C22 C25 1.518(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.413(2) . ?
C26 C31 1.425(2) . ?
C26 C35 1.409(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.359(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.403(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.362(2) . ?
C30 H30 0.9500 . ?
C30 C31 1.410(2) . ?
C31 C32 1.418(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.360(2) . ?
C33 C34 1.407(2) . ?
C33 C36 1.499(2) . ?
C34 C35 1.359(2) . ?
C34 C37 1.471(2) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C38 H38 1.0000 . ?
C38 C39 1.518(2) . ?
C38 C46 1.537(2) . ?
C39 C40 1.386(2) . ?
C39 C44 1.374(2) . ?
C40 H40 0.9500 . ?
C40 C41 1.381(2) . ?
C41 H41 0.9500 . ?
C41 C42 1.381(3) . ?
C42 C43 1.375(3) . ?
C42 C45 1.511(3) . ?
C43 H43 0.9500 . ?
C43 C44 1.387(3) . ?
C44 H44 0.9500 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C47 C48 1.521(3) . ?
C47 C49 1.517(3) . ?
C47 C50 1.515(2) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 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
C11 N1 C12 113.08(13) . . ?
C11 N1 C13 121.33(13) . . ?
C13 N1 C12 125.48(13) . . ?
C21 N2 H2 117.2 . . ?
C21 N2 C22 125.67(13) . . ?
C22 N2 H2 117.2 . . ?
C37 N3 C36 113.74(13) . . ?
C37 N3 C38 122.17(13) . . ?
C38 N3 C36 123.92(12) . . ?
C46 N4 H4A 117.2 . . ?
C46 N4 C47 125.51(14) . . ?
C47 N4 H4A 117.2 . . ?
C2 C1 C6 119.31(16) . . ?
C10 C1 C2 121.54(16) . . ?
C10 C1 C6 119.10(16) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 C1 121.13(18) . . ?
C3 C2 H2A 119.4 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.75(19) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.85(17) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.02(18) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 117.92(17) . . ?
C7 C6 C1 120.48(15) . . ?
C7 C6 C5 121.59(16) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 118.97(15) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 C9 120.06(16) . . ?
C7 C8 C12 130.79(15) . . ?
C9 C8 C12 109.09(13) . . ?
C8 C9 C11 108.22(14) . . ?
C10 C9 C8 122.81(15) . . ?
C10 C9 C11 128.88(14) . . ?
C1 C10 H10 120.7 . . ?
C9 C10 C1 118.56(15) . . ?
C9 C10 H10 120.7 . . ?
O1 C11 N1 125.16(15) . . ?
O1 C11 C9 127.54(16) . . ?
N1 C11 C9 107.30(13) . . ?
N1 C12 C8 102.27(13) . . ?
N1 C12 H12A 111.3 . . ?
N1 C12 H12B 111.3 . . ?
C8 C12 H12A 111.3 . . ?
C8 C12 H12B 111.3 . . ?
H12A C12 H12B 109.2 . . ?
N1 C13 H13 107.0 . . ?
N1 C13 C14 111.64(12) . . ?
N1 C13 C21 111.43(12) . . ?
C14 C13 H13 107.0 . . ?
C14 C13 C21 112.51(13) . . ?
C21 C13 H13 107.0 . . ?
C15 C14 C13 118.15(16) . . ?
C20 C14 C13 123.54(14) . . ?
C20 C14 C15 118.28(15) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.30(19) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.70(17) . . ?
C17 C16 H16 119.2 . . ?
C16 C17 C18 120.80(18) . . ?
C19 C17 C16 117.78(16) . . ?
C19 C17 C18 121.4(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19 119.5 . . ?
C17 C19 C20 121.07(18) . . ?
C20 C19 H19 119.5 . . ?
C14 C20 C19 120.85(16) . . ?
C14 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
O2 C21 N2 124.89(14) . . ?
O2 C21 C13 121.16(14) . . ?
N2 C21 C13 113.94(13) . . ?
N2 C22 C23 108.31(14) . . ?
N2 C22 C24 106.38(13) . . ?
N2 C22 C25 111.07(13) . . ?
C23 C22 C24 110.24(14) . . ?
C25 C22 C23 111.09(15) . . ?
C25 C22 C24 109.63(15) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 C31 118.54(16) . . ?
C35 C26 C27 122.03(16) . . ?
C35 C26 C31 119.40(15) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.21(17) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.36(18) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.02(17) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.3 . . ?
C29 C30 C31 121.46(16) . . ?
C31 C30 H30 119.3 . . ?
C30 C31 C26 118.40(15) . . ?
C30 C31 C32 121.58(15) . . ?
C32 C31 C26 119.97(15) . . ?
C31 C32 H32 120.6 . . ?
C33 C32 C31 118.81(15) . . ?
C33 C32 H32 120.6 . . ?
C32 C33 C34 120.95(15) . . ?
C32 C33 C36 130.23(14) . . ?
C34 C33 C36 108.76(14) . . ?
C33 C34 C37 108.89(14) . . ?
C35 C34 C33 121.92(16) . . ?
C35 C34 C37 129.06(15) . . ?
C26 C35 H35 120.5 . . ?
C34 C35 C26 118.92(15) . . ?
C34 C35 H35 120.5 . . ?
N3 C36 C33 102.22(12) . . ?
N3 C36 H36A 111.3 . . ?
N3 C36 H36B 111.3 . . ?
C33 C36 H36A 111.3 . . ?
C33 C36 H36B 111.3 . . ?
H36A C36 H36B 109.2 . . ?
O3 C37 N3 125.39(16) . . ?
O3 C37 C34 128.28(15) . . ?
N3 C37 C34 106.33(14) . . ?
N3 C38 H38 107.4 . . ?
N3 C38 C39 111.51(13) . . ?
N3 C38 C46 109.09(13) . . ?
C39 C38 H38 107.4 . . ?
C39 C38 C46 113.83(13) . . ?
C46 C38 H38 107.4 . . ?
C40 C39 C38 118.93(14) . . ?
C44 C39 C38 123.21(14) . . ?
C44 C39 C40 117.83(15) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 C39 121.17(16) . . ?
C41 C40 H40 119.4 . . ?
C40 C41 H41 119.4 . . ?
C42 C41 C40 121.17(16) . . ?
C42 C41 H41 119.4 . . ?
C41 C42 C45 121.41(17) . . ?
C43 C42 C41 117.38(16) . . ?
C43 C42 C45 121.20(18) . . ?
C42 C43 H43 119.1 . . ?
C42 C43 C44 121.83(18) . . ?
C44 C43 H43 119.1 . . ?
C39 C44 C43 120.62(16) . . ?
C39 C44 H44 119.7 . . ?
C43 C44 H44 119.7 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
O4 C46 N4 124.89(15) . . ?
O4 C46 C38 120.84(15) . . ?
N4 C46 C38 114.27(14) . . ?
N4 C47 C48 110.01(15) . . ?
N4 C47 C49 105.66(14) . . ?
N4 C47 C50 110.48(14) . . ?
C49 C47 C48 110.60(17) . . ?
C50 C47 C48 110.35(17) . . ?
C50 C47 C49 109.65(16) . . ?
C47 C48 H48A 109.5 . . ?
C47 C48 H48B 109.5 . . ?
C47 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C47 C49 H49A 109.5 . . ?
C47 C49 H49B 109.5 . . ?
C47 C49 H49C 109.5 . . ?
H49A C49 H49B 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C47 C50 H50A 109.5 . . ?
C47 C50 H50B 109.5 . . ?
C47 C50 H50C 109.5 . . ?
H50A C50 H50B 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 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
N1 C13 C14 C15 57.79(18) . . . . ?
N1 C13 C14 C20 -124.23(16) . . . . ?
N1 C13 C21 O2 41.6(2) . . . . ?
N1 C13 C21 N2 -139.80(13) . . . . ?
N3 C38 C39 C40 49.2(2) . . . . ?
N3 C38 C39 C44 -132.74(18) . . . . ?
N3 C38 C46 O4 43.4(2) . . . . ?
N3 C38 C46 N4 -136.03(14) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
C1 C6 C7 C8 1.1(2) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C2 C1 C6 C7 -177.40(14) . . . . ?
C2 C1 C10 C9 176.06(14) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 -1.5(2) . . . . ?
C4 C5 C6 C7 177.24(15) . . . . ?
C5 C6 C7 C8 -177.53(15) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C10 C9 -1.1(2) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C6 C7 C8 C12 176.10(15) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C7 C8 C9 C11 176.46(13) . . . . ?
C7 C8 C12 N1 -175.37(15) . . . . ?
C8 C9 C10 C1 1.5(2) . . . . ?
C8 C9 C11 O1 -179.22(15) . . . . ?
C8 C9 C11 N1 -0.19(16) . . . . ?
C9 C8 C12 N1 1.84(15) . . . . ?
C10 C1 C2 C3 -177.30(15) . . . . ?
C10 C1 C6 C5 178.58(14) . . . . ?
C10 C1 C6 C7 -0.1(2) . . . . ?
C10 C9 C11 O1 -2.5(3) . . . . ?
C10 C9 C11 N1 176.50(15) . . . . ?
C11 N1 C12 C8 -2.05(16) . . . . ?
C11 N1 C13 C14 -115.23(15) . . . . ?
C11 N1 C13 C21 118.03(15) . . . . ?
C11 C9 C10 C1 -174.78(14) . . . . ?
C12 N1 C11 O1 -179.47(14) . . . . ?
C12 N1 C11 C9 1.47(17) . . . . ?
C12 N1 C13 C14 60.60(18) . . . . ?
C12 N1 C13 C21 -66.15(18) . . . . ?
C12 C8 C9 C10 -178.03(14) . . . . ?
C12 C8 C9 C11 -1.10(16) . . . . ?
C13 N1 C11 O1 -3.2(2) . . . . ?
C13 N1 C11 C9 177.77(12) . . . . ?
C13 N1 C12 C8 -178.17(13) . . . . ?
C13 C14 C15 C16 179.06(15) . . . . ?
C13 C14 C20 C19 -178.73(14) . . . . ?
C14 C13 C21 O2 -84.72(18) . . . . ?
C14 C13 C21 N2 93.93(15) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C14 C20 C19 -0.8(2) . . . . ?
C15 C16 C17 C18 177.65(18) . . . . ?
C15 C16 C17 C19 -1.0(3) . . . . ?
C16 C17 C19 C20 1.3(3) . . . . ?
C17 C19 C20 C14 -0.4(2) . . . . ?
C18 C17 C19 C20 -177.42(17) . . . . ?
C20 C14 C15 C16 1.0(2) . . . . ?
C21 N2 C22 C23 -62.5(2) . . . . ?
C21 N2 C22 C24 178.98(15) . . . . ?
C21 N2 C22 C25 59.7(2) . . . . ?
C21 C13 C14 C15 -176.05(14) . . . . ?
C21 C13 C14 C20 1.9(2) . . . . ?
C22 N2 C21 O2 -3.8(2) . . . . ?
C22 N2 C21 C13 177.64(14) . . . . ?
C26 C27 C28 C29 -0.5(3) . . . . ?
C26 C31 C32 C33 1.1(2) . . . . ?
C27 C26 C31 C30 -0.6(2) . . . . ?
C27 C26 C31 C32 -178.16(15) . . . . ?
C27 C26 C35 C34 177.02(17) . . . . ?
C27 C28 C29 C30 -0.3(3) . . . . ?
C28 C29 C30 C31 0.5(3) . . . . ?
C29 C30 C31 C26 -0.1(2) . . . . ?
C29 C30 C31 C32 177.40(15) . . . . ?
C30 C31 C32 C33 -176.30(14) . . . . ?
C31 C26 C27 C28 0.9(3) . . . . ?
C31 C26 C35 C34 -1.0(2) . . . . ?
C31 C32 C33 C34 -1.1(2) . . . . ?
C31 C32 C33 C36 175.75(14) . . . . ?
C32 C33 C34 C35 0.0(2) . . . . ?
C32 C33 C34 C37 176.29(13) . . . . ?
C32 C33 C36 N3 -174.99(15) . . . . ?
C33 C34 C35 C26 1.0(2) . . . . ?
C33 C34 C37 O3 -179.34(15) . . . . ?
C33 C34 C37 N3 -0.42(17) . . . . ?
C34 C33 C36 N3 2.16(16) . . . . ?
C35 C26 C27 C28 -177.09(18) . . . . ?
C35 C26 C31 C30 177.42(14) . . . . ?
C35 C26 C31 C32 -0.1(2) . . . . ?
C35 C34 C37 O3 -3.4(3) . . . . ?
C35 C34 C37 N3 175.52(16) . . . . ?
C36 N3 C37 O3 -179.10(14) . . . . ?
C36 N3 C37 C34 1.94(17) . . . . ?
C36 N3 C38 C39 55.59(18) . . . . ?
C36 N3 C38 C46 -71.00(18) . . . . ?
C36 C33 C34 C35 -177.45(14) . . . . ?
C36 C33 C34 C37 -1.17(17) . . . . ?
C37 N3 C36 C33 -2.56(16) . . . . ?
C37 N3 C38 C39 -129.48(15) . . . . ?
C37 N3 C38 C46 103.94(16) . . . . ?
C37 C34 C35 C26 -174.42(15) . . . . ?
C38 N3 C36 C33 172.75(13) . . . . ?
C38 N3 C37 O3 5.5(2) . . . . ?
C38 N3 C37 C34 -173.47(13) . . . . ?
C38 C39 C40 C41 177.63(16) . . . . ?
C38 C39 C44 C43 -177.12(19) . . . . ?
C39 C38 C46 O4 -81.9(2) . . . . ?
C39 C38 C46 N4 98.73(17) . . . . ?
C39 C40 C41 C42 0.0(3) . . . . ?
C40 C39 C44 C43 0.9(3) . . . . ?
C40 C41 C42 C43 0.2(3) . . . . ?
C40 C41 C42 C45 179.56(19) . . . . ?
C41 C42 C43 C44 0.3(3) . . . . ?
C42 C43 C44 C39 -0.8(3) . . . . ?
C44 C39 C40 C41 -0.5(3) . . . . ?
C45 C42 C43 C44 -179.1(2) . . . . ?
C46 N4 C47 C48 -61.2(2) . . . . ?
C46 N4 C47 C49 179.39(17) . . . . ?
C46 N4 C47 C50 60.9(2) . . . . ?
C46 C38 C39 C40 173.19(15) . . . . ?
C46 C38 C39 C44 -8.8(2) . . . . ?
C47 N4 C46 O4 -0.6(3) . . . . ?
C47 N4 C46 C38 178.77(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1009252'
