# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# 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_shelxl
_audit_creation_date             2013-08-14
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H14 O2, C17 H11 O2'
_chemical_formula_sum            'C37 H26 O4'
_chemical_formula_weight         534.58
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, z'
3 'x+1/2, -y+1/2, -z'
4 '-x+1/2, y+1/2, -z'

_cell_length_a                   13.1215(7)
_cell_length_b                   11.0922(5)
_cell_length_c                   9.3453(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1360.17(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1228
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      28.7028
_cell_measurement_theta_min      3.0987
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9744
_exptl_absorpt_correction_T_min  0.9655
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            4423
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.10
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1685
_reflns_number_total             2565
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       0.034(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2565
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0426P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1177
_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. Others
 Fixed Sof: H9A(0.5) H3(0.5)
 Fixed U13: C9(0)
 Fixed U23: C9(0)
 Fixed Uiso: H2(0.12) H13(0.08) H19(0.09) H16(0.101) H2A(0.091) H15(0.109)
 H14(0.1) H18(0.094) H1(0.117) H5(0.131) H7(0.112) H9A(0.146) H3(0.146)
 H6(0.143)
 Fixed X: H2(-0.5735) H13(-0.4099) H19(-0.7569) H16(-0.6827) H2A(-0.8197) H15(-
 0.5523) H14(-0.4159) H18(-0.7609) H1(-0.68) H5(-0.779) H7(-0.9116) C9(-1) H9A(-
 1.0499) H3(-0.9501) H6(-0.6622)
 Fixed Y: H2(0.0963) H13(-0.1078) H19(-0.1041) H16(-0.3734) H2A(0.2243) H15(-
 0.3975) H14(-0.2659) H18(-0.2594) H1(0.1183) H5(-0.1748) H7(-0.1511) C9(0)
 H9A(-0.0393) H3(0.0393) H6(-0.0813)
 Fixed Z: H2(-0.7191) H13(-0.3222) H19(-0.6859) H16(-0.3241) H2A(-0.0667) H15(-
 0.1665) H14(-0.1653) H18(-0.5271) H1(0.0149) H5(-0.1884) H7(-0.3761) H9A(-
 0.4719) H3(-0.4719) H6(-0.0475)
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O -0.62761(14) 0.05938(19) -0.7174(2) 0.0802(6) Uani 1 1 d . . .
H2 H -0.5735 0.0963 -0.7191 0.120 Uiso 1 1 calc R . .
O1 O -1.01435(16) -0.26428(18) -0.1932(2) 0.0879(7) Uani 1 1 d . . .
C12 C -0.54375(19) -0.1433(2) -0.4258(3) 0.0567(6) Uani 1 1 d . . .
C17 C -0.6269(2) -0.2244(3) -0.4266(3) 0.0673(8) Uani 1 1 d . . .
C10 C -0.62166(19) -0.0320(2) -0.6196(3) 0.0615(7) Uani 1 1 d . . .
C11 C -0.54273(17) -0.0440(2) -0.5249(3) 0.0521(6) Uani 1 1 d . . .
C8 C -1.0259(2) -0.1583(3) -0.2272(3) 0.0716(8) Uani 1 1 d . . .
C13 C -0.4648(2) -0.1608(3) -0.3246(3) 0.0667(7) Uani 1 1 d . . .
H13 H -0.4099 -0.1078 -0.3222 0.080 Uiso 1 1 calc R . .
C19 C -0.7041(2) -0.1138(3) -0.6206(4) 0.0751(9) Uani 1 1 d . . .
H19 H -0.7569 -0.1041 -0.6859 0.090 Uiso 1 1 calc R . .
C3 C -0.8841(2) 0.0886(2) -0.1786(3) 0.0648(7) Uani 1 1 d . . .
C16 C -0.6282(3) -0.3200(3) -0.3256(4) 0.0842(10) Uani 1 1 d . . .
H16 H -0.6827 -0.3734 -0.3241 0.101 Uiso 1 1 calc R . .
C2 C -0.8117(3) 0.1438(3) -0.0918(3) 0.0762(9) Uani 1 1 d . . .
H2A H -0.8197 0.2243 -0.0667 0.091 Uiso 1 1 calc R . .
C15 C -0.5506(3) -0.3340(3) -0.2314(4) 0.0906(11) Uani 1 1 d . . .
H15 H -0.5523 -0.3975 -0.1665 0.109 Uiso 1 1 calc R . .
C14 C -0.4686(3) -0.2548(3) -0.2305(3) 0.0830(9) Uani 1 1 d . . .
H14 H -0.4159 -0.2659 -0.1653 0.100 Uiso 1 1 calc R . .
C18 C -0.7060(2) -0.2064(3) -0.5262(4) 0.0786(10) Uani 1 1 d . . .
H18 H -0.7609 -0.2594 -0.5271 0.094 Uiso 1 1 calc R . .
C4 C -0.8718(3) -0.0311(3) -0.2181(3) 0.0748(9) Uani 1 1 d . . .
C1 C -0.7284(3) 0.0810(4) -0.0428(4) 0.0973(11) Uani 1 1 d . . .
H1 H -0.6800 0.1183 0.0149 0.117 Uiso 1 1 calc R . .
C5 C -0.7875(3) -0.0939(3) -0.1653(5) 0.1092(15) Uani 1 1 d . . .
H5 H -0.7790 -0.1748 -0.1884 0.131 Uiso 1 1 calc R . .
C7 C -0.9477(3) -0.0928(3) -0.3158(3) 0.0931(11) Uani 1 1 d . . .
H7 H -0.9116 -0.1511 -0.3761 0.112 Uiso 1 1 calc R . .
C9 C -1.0000 0.0000 -0.4111(5) 0.122(2) Uani 1 2 d S . .
H9A H -1.0499 -0.0393 -0.4719 0.146 Uiso 0.50 1 calc PR . .
H9B H -0.9501 0.0393 -0.4719 0.146 Uiso 0.50 1 calc PR . .
C6 C -0.7181(3) -0.0380(4) -0.0807(6) 0.1194(16) Uani 1 1 d . . .
H6 H -0.6622 -0.0813 -0.0475 0.143 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
O2 H2 0.8200 . ?
O2 C10 1.368(3) . ?
O1 C8 1.227(3) . ?
C12 C17 1.414(3) . ?
C12 C11 1.439(3) . ?
C12 C13 1.416(3) . ?
C17 C16 1.419(4) . ?
C17 C18 1.408(4) . ?
C10 C11 1.369(3) . ?
C10 C19 1.412(4) . ?
C11 C11 1.487(5) 2_455 ?
C8 C3 1.483(4) 2_355 ?
C8 C7 1.505(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.355(4) . ?
C3 C8 1.483(4) 2_355 ?
C3 C2 1.391(4) . ?
C3 C4 1.388(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.355(4) . ?
C2 H2A 0.9300 . ?
C2 C1 1.375(4) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(4) . ?
C14 H14 0.9300 . ?
C18 H18 0.9300 . ?
C4 C5 1.396(5) . ?
C4 C7 1.514(4) . ?
C1 H1 0.9300 . ?
C1 C6 1.373(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.356(6) . ?
C7 H7 0.9800 . ?
C7 C9 1.525(4) . ?
C9 C7 1.525(4) 2_355 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 H2 109.5 . . ?
C17 C12 C11 119.4(3) . . ?
C17 C12 C13 118.8(3) . . ?
C13 C12 C11 121.8(2) . . ?
C12 C17 C16 118.7(3) . . ?
C18 C17 C12 118.8(3) . . ?
C18 C17 C16 122.5(3) . . ?
O2 C10 C11 123.2(2) . . ?
O2 C10 C19 115.3(3) . . ?
C11 C10 C19 121.5(3) . . ?
C12 C11 C11 120.6(2) . 2_455 ?
C10 C11 C12 118.9(2) . . ?
C10 C11 C11 120.5(2) . 2_455 ?
O1 C8 C3 121.2(3) . 2_355 ?
O1 C8 C7 121.4(3) . . ?
C3 C8 C7 117.4(3) 2_355 . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C10 C19 H19 120.1 . . ?
C18 C19 C10 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C2 C3 C8 119.6(3) . 2_355 ?
C4 C3 C8 120.7(3) . 2_355 ?
C4 C3 C2 119.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 C17 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C3 C2 H2A 119.5 . . ?
C1 C2 C3 121.0(3) . . ?
C1 C2 H2A 119.5 . . ?
C16 C15 H15 119.6 . . ?
C16 C15 C14 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
C13 C14 C15 120.6(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C17 C18 H18 119.2 . . ?
C19 C18 C17 121.6(3) . . ?
C19 C18 H18 119.2 . . ?
C3 C4 C5 118.4(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 120.6(3) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 C2 118.6(4) . . ?
C6 C1 H1 120.7 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.6(4) . . ?
C6 C5 H5 119.7 . . ?
C8 C7 C4 109.6(2) . . ?
C8 C7 H7 109.1 . . ?
C8 C7 C9 109.9(3) . . ?
C4 C7 H7 109.1 . . ?
C4 C7 C9 110.1(2) . . ?
C9 C7 H7 109.1 . . ?
C7 C9 C7 108.5(3) . 2_355 ?
C7 C9 H9A 110.0 2_355 . ?
C7 C9 H9A 110.0 . . ?
C7 C9 H9B 110.0 2_355 . ?
C7 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
C1 C6 H6 119.2 . . ?
C5 C6 C1 121.6(4) . . ?
C5 C6 H6 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 2.10 2.827(3) 148.5 4_354

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 C10 C11 C12 179.8(2) . . . . ?
O2 C10 C11 C11 -0.4(4) . . . 2_455 ?
O2 C10 C19 C18 -179.0(2) . . . . ?
O1 C8 C7 C4 -91.5(4) . . . . ?
O1 C8 C7 C9 147.4(3) . . . . ?
C12 C17 C16 C15 -0.8(4) . . . . ?
C12 C17 C18 C19 0.1(4) . . . . ?
C12 C13 C14 C15 -0.8(4) . . . . ?
C17 C12 C11 C10 -1.3(3) . . . . ?
C17 C12 C11 C11 178.9(2) . . . 2_455 ?
C17 C12 C13 C14 0.6(3) . . . . ?
C17 C16 C15 C14 0.6(4) . . . . ?
C10 C19 C18 C17 -0.5(4) . . . . ?
C11 C12 C17 C16 -178.3(2) . . . . ?
C11 C12 C17 C18 0.8(3) . . . . ?
C11 C12 C13 C14 179.0(2) . . . . ?
C11 C10 C19 C18 0.1(4) . . . . ?
C8 C3 C2 C1 178.7(3) 2_355 . . . ?
C8 C3 C4 C5 -177.7(3) 2_355 . . . ?
C8 C3 C4 C7 2.1(4) 2_355 . . . ?
C8 C7 C9 C7 62.61(18) . . . 2_355 ?
C13 C12 C17 C16 0.2(3) . . . . ?
C13 C12 C17 C18 179.3(2) . . . . ?
C13 C12 C11 C10 -179.7(2) . . . . ?
C13 C12 C11 C11 0.5(3) . . . 2_455 ?
C19 C10 C11 C12 0.8(3) . . . . ?
C19 C10 C11 C11 -179.4(2) . . . 2_455 ?
C3 C8 C7 C4 86.6(3) 2_355 . . . ?
C3 C8 C7 C9 -34.5(3) 2_355 . . . ?
C3 C2 C1 C6 -0.2(5) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C3 C4 C7 C8 -94.5(3) . . . . ?
C3 C4 C7 C9 26.5(3) . . . . ?
C16 C17 C18 C19 179.2(2) . . . . ?
C16 C15 C14 C13 0.2(4) . . . . ?
C2 C3 C4 C5 1.9(4) . . . . ?
C2 C3 C4 C7 -178.3(2) . . . . ?
C2 C1 C6 C5 0.3(6) . . . . ?
C18 C17 C16 C15 -179.9(3) . . . . ?
C4 C3 C2 C1 -0.9(4) . . . . ?
C4 C5 C6 C1 0.7(6) . . . . ?
C4 C7 C9 C7 -58.18(17) . . . 2_355 ?
C5 C4 C7 C8 85.3(4) . . . . ?
C5 C4 C7 C9 -153.7(3) . . . . ?
C7 C4 C5 C6 178.4(3) . . . . ?

_database_code_depnum_ccdc_archive 'CCDC 969970'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24.80 H24 N1.60'
_chemical_formula_weight         344.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   14.4556(17)
_cell_length_b                   10.0330(7)
_cell_length_c                   17.453(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.716(17)
_cell_angle_gamma                90.00
_cell_volume                     2351.6(5)
_cell_formula_units_Z            5
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1916
_cell_measurement_theta_min      3.2881
_cell_measurement_theta_max      69.5887

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8471
_exptl_absorpt_correction_T_max  0.8821
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9573
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         69.72
_reflns_number_total             4326
_reflns_number_gt                2810
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+3.9567P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4326
_refine_ls_number_parameters     299
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1400
_refine_ls_R_factor_gt           0.1056
_refine_ls_wR_factor_ref         0.2526
_refine_ls_wR_factor_gt          0.2296
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N2 N 0.7663(3) 0.3691(4) -0.0254(3) 0.0941(14) Uani 1 1 d U . .
H2 H 0.7540 0.2861 -0.0212 0.113 Uiso 1 1 calc R . .
C6 C 0.7947(7) 0.4016(7) 0.5675(4) 0.131(3) Uani 1 1 d . . .
H6 H 0.8486 0.3827 0.6156 0.157 Uiso 1 1 calc R . .
N1 N 0.7815(4) 0.4704(4) 0.3178(3) 0.0990(15) Uani 1 1 d . . .
H1 H 0.7820 0.3860 0.3267 0.119 Uiso 1 1 calc R . .
C19 C 0.8910(3) 0.4368(4) 0.1542(3) 0.0662(11) Uani 1 1 d . . .
C12 C 0.6633(3) 0.4309(4) 0.0586(3) 0.0639(10) Uani 1 1 d . . .
C26 C 0.8322(3) 0.3128(5) -0.1333(3) 0.0682(11) Uani 1 1 d . . .
C11 C 0.6590(3) 0.4774(4) 0.1314(3) 0.0699(11) Uani 1 1 d . . .
C17 C 0.7399(4) 0.4768(5) 0.0234(3) 0.0781(12) Uani 1 1 d U . .
H17 H 0.7083 0.5483 -0.0158 0.094 Uiso 1 1 calc R . .
C2 C 0.7274(4) 0.5007(4) 0.4324(3) 0.0771(13) Uani 1 1 d . . .
C24 C 0.8848(3) 0.4379(5) 0.2318(3) 0.0773(13) Uani 1 1 d . . .
C18 C 0.8277(4) 0.5361(5) 0.0871(3) 0.0828(13) Uani 1 1 d U . .
H18 H 0.8700 0.5758 0.0604 0.099 Uiso 1 1 calc R . .
C25 C 0.8128(4) 0.4162(5) -0.0787(3) 0.0841(14) Uani 1 1 d . . .
H25A H 0.8758 0.4568 -0.0454 0.101 Uiso 1 1 calc R . .
H25B H 0.7713 0.4855 -0.1135 0.101 Uiso 1 1 calc R . .
C1 C 0.7451(4) 0.5665(4) 0.3621(3) 0.0809(13) Uani 1 1 d . . .
H1A H 0.6835 0.6055 0.3248 0.097 Uiso 1 1 calc R . .
H1B H 0.7935 0.6375 0.3829 0.097 Uiso 1 1 calc R . .
C10 C 0.7847(4) 0.6502(4) 0.1253(3) 0.0808(12) Uani 1 1 d U . .
H10A H 0.8374 0.7106 0.1569 0.097 Uiso 1 1 calc R . .
H10B H 0.7349 0.7004 0.0821 0.097 Uiso 1 1 calc R . .
C31 C 0.9018(4) 0.3392(6) -0.1682(3) 0.0870(14) Uani 1 1 d . . .
H31 H 0.9359 0.4198 -0.1568 0.104 Uiso 1 1 calc R . .
C8 C 0.8179(4) 0.5284(5) 0.2560(3) 0.0860(14) Uani 1 1 d . . .
H8 H 0.8593 0.6046 0.2834 0.103 Uiso 1 1 calc R . .
C9 C 0.7378(4) 0.5843(4) 0.1817(3) 0.0854(14) Uani 1 1 d U . .
H9 H 0.7028 0.6534 0.2001 0.103 Uiso 1 1 calc R . .
C13 C 0.5915(3) 0.3407(5) 0.0122(3) 0.0775(13) Uani 1 1 d . . .
H13 H 0.5933 0.3091 -0.0373 0.093 Uiso 1 1 calc R . .
C27 C 0.7826(4) 0.1933(5) -0.1525(3) 0.0877(15) Uani 1 1 d . . .
H27 H 0.7346 0.1729 -0.1306 0.105 Uiso 1 1 calc R . .
C29 C 0.8723(4) 0.1307(6) -0.2371(3) 0.0932(16) Uani 1 1 d . . .
H29 H 0.8858 0.0696 -0.2717 0.112 Uiso 1 1 calc R . .
C14 C 0.5171(3) 0.2970(5) 0.0385(4) 0.0908(15) Uani 1 1 d . . .
H14 H 0.4698 0.2357 0.0075 0.109 Uiso 1 1 calc R . .
C16 C 0.5838(4) 0.4363(6) 0.1554(3) 0.0875(15) Uani 1 1 d . . .
H16 H 0.5799 0.4713 0.2035 0.105 Uiso 1 1 calc R . .
C3 C 0.6348(5) 0.4632(5) 0.4276(4) 0.0962(16) Uani 1 1 d . . .
H3 H 0.5798 0.4854 0.3810 0.115 Uiso 1 1 calc R . .
C23 C 0.9479(4) 0.3454(5) 0.2915(3) 0.0913(15) Uani 1 1 d . . .
H23 H 0.9464 0.3427 0.3444 0.110 Uiso 1 1 calc R . .
C7 C 0.8081(5) 0.4703(5) 0.5038(3) 0.0947(16) Uani 1 1 d . . .
H7 H 0.8718 0.4965 0.5088 0.114 Uiso 1 1 calc R . .
C21 C 1.0149(4) 0.2651(5) 0.1972(4) 0.0960(16) Uani 1 1 d . . .
H21 H 1.0585 0.2090 0.1846 0.115 Uiso 1 1 calc R . .
C30 C 0.9217(4) 0.2500(6) -0.2189(3) 0.0970(17) Uani 1 1 d . . .
H30 H 0.9692 0.2703 -0.2414 0.116 Uiso 1 1 calc R . .
C15 C 0.5149(4) 0.3464(6) 0.1115(4) 0.0949(16) Uani 1 1 d . . .
H15 H 0.4660 0.3180 0.1305 0.114 Uiso 1 1 calc R . .
C20 C 0.9565(3) 0.3501(5) 0.1399(3) 0.0824(13) Uani 1 1 d . . .
H20 H 0.9607 0.3501 0.0880 0.099 Uiso 1 1 calc R . .
C22 C 1.0102(4) 0.2612(6) 0.2711(4) 0.0966(16) Uani 1 1 d . . .
H22 H 1.0496 0.2008 0.3099 0.116 Uiso 1 1 calc R . .
C28 C 0.8031(5) 0.1035(6) -0.2036(3) 0.1016(17) Uani 1 1 d . . .
H28 H 0.7690 0.0229 -0.2154 0.122 Uiso 1 1 calc R . .
C5 C 0.6987(10) 0.3609(7) 0.5583(6) 0.148(4) Uani 1 1 d . . .
H5 H 0.6888 0.3111 0.5996 0.177 Uiso 1 1 calc R . .
C4 C 0.6210(7) 0.3933(7) 0.4904(6) 0.133(3) Uani 1 1 d . . .
H4 H 0.5571 0.3683 0.4855 0.160 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
N2 C25 1.416(5) . ?
N2 C17 1.509(6) . ?
N2 H2 0.8600 . ?
C6 C7 1.382(8) . ?
C6 C5 1.397(11) . ?
C6 H6 0.9300 . ?
N1 C1 1.451(5) . ?
N1 C8 1.481(6) . ?
N1 H1 0.8600 . ?
C19 C20 1.375(6) . ?
C19 C24 1.389(6) . ?
C19 C18 1.552(6) . ?
C12 C11 1.377(6) . ?
C12 C13 1.390(6) . ?
C12 C17 1.523(6) . ?
C26 C27 1.372(6) . ?
C26 C31 1.382(6) . ?
C26 C25 1.504(6) . ?
C11 C16 1.365(6) . ?
C11 C9 1.575(7) . ?
C17 C18 1.469(7) . ?
C17 H17 0.9800 . ?
C2 C3 1.364(7) . ?
C2 C7 1.389(7) . ?
C2 C1 1.497(6) . ?
C24 C23 1.441(7) . ?
C24 C8 1.497(6) . ?
C18 C10 1.565(6) . ?
C18 H18 0.9800 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C10 C9 1.536(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C31 C30 1.362(7) . ?
C31 H31 0.9300 . ?
C8 C9 1.492(7) . ?
C8 H8 0.9800 . ?
C9 H9 0.9800 . ?
C13 C14 1.386(6) . ?
C13 H13 0.9300 . ?
C27 C28 1.375(7) . ?
C27 H27 0.9300 . ?
C29 C28 1.361(7) . ?
C29 C30 1.369(7) . ?
C29 H29 0.9300 . ?
C14 C15 1.379(7) . ?
C14 H14 0.9300 . ?
C16 C15 1.352(7) . ?
C16 H16 0.9300 . ?
C3 C4 1.376(9) . ?
C3 H3 0.9300 . ?
C23 C22 1.375(7) . ?
C23 H23 0.9300 . ?
C7 H7 0.9300 . ?
C21 C22 1.316(7) . ?
C21 C20 1.348(7) . ?
C21 H21 0.9300 . ?
C30 H30 0.9300 . ?
C15 H15 0.9300 . ?
C20 H20 0.9300 . ?
C22 H22 0.9300 . ?
C28 H28 0.9300 . ?
C5 C4 1.337(11) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?

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
C25 N2 C17 114.3(4) . . ?
C25 N2 H2 122.8 . . ?
C17 N2 H2 122.8 . . ?
C7 C6 C5 118.9(8) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C1 N1 C8 115.0(4) . . ?
C1 N1 H1 122.5 . . ?
C8 N1 H1 122.5 . . ?
C20 C19 C24 118.7(4) . . ?
C20 C19 C18 121.5(4) . . ?
C24 C19 C18 119.8(4) . . ?
C11 C12 C13 118.6(4) . . ?
C11 C12 C17 123.9(4) . . ?
C13 C12 C17 117.4(4) . . ?
C27 C26 C31 117.4(4) . . ?
C27 C26 C25 123.7(4) . . ?
C31 C26 C25 118.9(4) . . ?
C16 C11 C12 119.6(4) . . ?
C16 C11 C9 121.9(4) . . ?
C12 C11 C9 118.4(4) . . ?
C18 C17 N2 112.9(4) . . ?
C18 C17 C12 111.7(4) . . ?
N2 C17 C12 112.6(4) . . ?
C18 C17 H17 106.3 . . ?
N2 C17 H17 106.3 . . ?
C12 C17 H17 106.3 . . ?
C3 C2 C7 118.3(5) . . ?
C3 C2 C1 122.2(5) . . ?
C7 C2 C1 119.4(5) . . ?
C19 C24 C23 116.6(4) . . ?
C19 C24 C8 124.2(5) . . ?
C23 C24 C8 119.2(5) . . ?
C17 C18 C19 114.5(4) . . ?
C17 C18 C10 104.5(4) . . ?
C19 C18 C10 111.3(4) . . ?
C17 C18 H18 108.8 . . ?
C19 C18 H18 108.8 . . ?
C10 C18 H18 108.8 . . ?
N2 C25 C26 115.5(4) . . ?
N2 C25 H25A 108.4 . . ?
C26 C25 H25A 108.4 . . ?
N2 C25 H25B 108.4 . . ?
C26 C25 H25B 108.4 . . ?
H25A C25 H25B 107.5 . . ?
N1 C1 C2 110.5(4) . . ?
N1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C9 C10 C18 107.3(3) . . ?
C9 C10 H10A 110.2 . . ?
C18 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
C18 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C30 C31 C26 121.6(5) . . ?
C30 C31 H31 119.2 . . ?
C26 C31 H31 119.2 . . ?
N1 C8 C9 114.2(4) . . ?
N1 C8 C24 114.1(4) . . ?
C9 C8 C24 110.9(4) . . ?
N1 C8 H8 105.6 . . ?
C9 C8 H8 105.6 . . ?
C24 C8 H8 105.6 . . ?
C8 C9 C10 109.5(4) . . ?
C8 C9 C11 113.4(4) . . ?
C10 C9 C11 109.6(4) . . ?
C8 C9 H9 108.1 . . ?
C10 C9 H9 108.1 . . ?
C11 C9 H9 108.1 . . ?
C14 C13 C12 121.1(4) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C26 C27 C28 120.8(4) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C28 C29 C30 118.6(5) . . ?
C28 C29 H29 120.7 . . ?
C30 C29 H29 120.7 . . ?
C15 C14 C13 118.6(5) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
C15 C16 C11 122.0(5) . . ?
C15 C16 H16 119.0 . . ?
C11 C16 H16 119.0 . . ?
C2 C3 C4 121.3(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C22 C23 C24 120.5(5) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C6 C7 C2 120.6(6) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
C22 C21 C20 120.1(5) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C31 C30 C29 120.5(5) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C16 C15 C14 120.0(5) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C21 C20 C19 123.3(5) . . ?
C21 C20 H20 118.4 . . ?
C19 C20 H20 118.4 . . ?
C21 C22 C23 120.8(5) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C29 C28 C27 121.1(5) . . ?
C29 C28 H28 119.4 . . ?
C27 C28 H28 119.4 . . ?
C4 C5 C6 120.2(8) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?

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
C13 C12 C11 C16 -1.4(6) . . . . ?
C17 C12 C11 C16 176.0(4) . . . . ?
C13 C12 C11 C9 -177.4(4) . . . . ?
C17 C12 C11 C9 0.0(6) . . . . ?
C25 N2 C17 C18 -70.1(6) . . . . ?
C25 N2 C17 C12 162.2(4) . . . . ?
C11 C12 C17 C18 20.5(6) . . . . ?
C13 C12 C17 C18 -162.1(4) . . . . ?
C11 C12 C17 N2 148.9(4) . . . . ?
C13 C12 C17 N2 -33.7(6) . . . . ?
C20 C19 C24 C23 -0.7(6) . . . . ?
C18 C19 C24 C23 -178.3(4) . . . . ?
C20 C19 C24 C8 179.1(4) . . . . ?
C18 C19 C24 C8 1.5(7) . . . . ?
N2 C17 C18 C19 -61.7(5) . . . . ?
C12 C17 C18 C19 66.4(5) . . . . ?
N2 C17 C18 C10 176.2(3) . . . . ?
C12 C17 C18 C10 -55.7(5) . . . . ?
C20 C19 C18 C17 78.8(5) . . . . ?
C24 C19 C18 C17 -103.6(5) . . . . ?
C20 C19 C18 C10 -162.9(4) . . . . ?
C24 C19 C18 C10 14.7(6) . . . . ?
C17 N2 C25 C26 -175.1(4) . . . . ?
C27 C26 C25 N2 20.7(7) . . . . ?
C31 C26 C25 N2 -160.9(5) . . . . ?
C8 N1 C1 C2 -170.0(5) . . . . ?
C3 C2 C1 N1 -100.1(6) . . . . ?
C7 C2 C1 N1 76.6(6) . . . . ?
C17 C18 C10 C9 75.8(5) . . . . ?
C19 C18 C10 C9 -48.3(5) . . . . ?
C27 C26 C31 C30 -0.7(8) . . . . ?
C25 C26 C31 C30 -179.2(5) . . . . ?
C1 N1 C8 C9 -70.4(6) . . . . ?
C1 N1 C8 C24 160.6(4) . . . . ?
C19 C24 C8 N1 148.6(5) . . . . ?
C23 C24 C8 N1 -31.7(6) . . . . ?
C19 C24 C8 C9 17.9(6) . . . . ?
C23 C24 C8 C9 -162.3(4) . . . . ?
N1 C8 C9 C10 176.0(4) . . . . ?
C24 C8 C9 C10 -53.4(5) . . . . ?
N1 C8 C9 C11 -61.2(5) . . . . ?
C24 C8 C9 C11 69.3(5) . . . . ?
C18 C10 C9 C8 70.1(5) . . . . ?
C18 C10 C9 C11 -54.9(5) . . . . ?
C16 C11 C9 C8 79.6(6) . . . . ?
C12 C11 C9 C8 -104.4(5) . . . . ?
C16 C11 C9 C10 -157.6(4) . . . . ?
C12 C11 C9 C10 18.3(6) . . . . ?
C11 C12 C13 C14 -0.5(7) . . . . ?
C17 C12 C13 C14 -178.0(4) . . . . ?
C31 C26 C27 C28 0.8(8) . . . . ?
C25 C26 C27 C28 179.2(5) . . . . ?
C12 C13 C14 C15 0.9(8) . . . . ?
C12 C11 C16 C15 2.8(8) . . . . ?
C9 C11 C16 C15 178.7(5) . . . . ?
C7 C2 C3 C4 -2.1(8) . . . . ?
C1 C2 C3 C4 174.7(5) . . . . ?
C19 C24 C23 C22 -0.1(7) . . . . ?
C8 C24 C23 C22 -179.9(5) . . . . ?
C5 C6 C7 C2 1.2(9) . . . . ?
C3 C2 C7 C6 1.3(7) . . . . ?
C1 C2 C7 C6 -175.6(5) . . . . ?
C26 C31 C30 C29 0.3(9) . . . . ?
C28 C29 C30 C31 0.1(9) . . . . ?
C11 C16 C15 C14 -2.4(8) . . . . ?
C13 C14 C15 C16 0.5(8) . . . . ?
C22 C21 C20 C19 0.7(8) . . . . ?
C24 C19 C20 C21 0.4(7) . . . . ?
C18 C19 C20 C21 178.0(5) . . . . ?
C20 C21 C22 C23 -1.5(9) . . . . ?
C24 C23 C22 C21 1.3(9) . . . . ?
C30 C29 C28 C27 0.0(9) . . . . ?
C26 C27 C28 C29 -0.5(9) . . . . ?
C7 C6 C5 C4 -2.9(11) . . . . ?
C6 C5 C4 C3 2.1(12) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        69.72
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.052
_database_code_depnum_ccdc_archive 'CCDC 969971'
#######################################################################
#
#                 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_shelxl

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H30 N2'
_chemical_formula_weight         430.57

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'

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

_cell_length_a                   26.280(2)
_cell_length_b                   9.4772(7)
_cell_length_c                   9.5917(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2388.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1407
_cell_measurement_theta_min      3.0943
_cell_measurement_theta_max      29.0227

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9754
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8404
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         26.37
_reflns_number_total             2432
_reflns_number_gt                1455
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0583P)²+0.3451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2432
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1090
_refine_ls_R_factor_gt           0.0589
_refine_ls_wR_factor_ref         0.1487
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C9 C 0.47918(8) 0.12308(19) 0.6351(2) 0.0469(5) Uani 1 1 d . . .
H9 H 0.4699 0.0638 0.5554 0.056 Uiso 1 1 calc R . .
N1 N 0.38880(8) 0.0940(2) 0.6979(2) 0.0620(6) Uani 1 1 d D . .
C11 C 0.43928(8) 0.26297(19) 0.8301(2) 0.0447(5) Uani 1 1 d . . .
C8 C 0.43119(7) 0.19674(19) 0.6874(2) 0.0471(5) Uani 1 1 d . . .
H8 H 0.4217 0.2709 0.6211 0.056 Uiso 1 1 calc R . .
C12 C 0.51910(8) 0.22882(18) 0.5870(2) 0.0427(5) Uani 1 1 d . . .
C13 C 0.51387(8) 0.2943(2) 0.4576(2) 0.0526(6) Uani 1 1 d . . .
H13 H 0.4858 0.2733 0.4023 0.063 Uiso 1 1 calc R . .
C16 C 0.59617(8) 0.3610(2) 0.6212(2) 0.0552(6) Uani 1 1 d . . .
H16 H 0.6238 0.3851 0.6768 0.066 Uiso 1 1 calc R . .
C10 C 0.5000 0.0277(3) 0.7500 0.0474(7) Uani 1 2 d S . .
H10A H 0.5268 -0.0321 0.7135 0.057 Uiso 0.50 1 calc PR . .
H10B H 0.4732 -0.0321 0.7865 0.057 Uiso 0.50 1 calc PR . .
C14 C 0.54962(9) 0.3902(2) 0.4101(2) 0.0598(6) Uani 1 1 d . . .
H14 H 0.5458 0.4323 0.3232 0.072 Uiso 1 1 calc R . .
C4 C 0.33398(8) 0.1858(2) 0.5017(3) 0.0574(6) Uani 1 1 d . . .
C15 C 0.59083(9) 0.4225(2) 0.4923(3) 0.0615(6) Uani 1 1 d . . .
H15 H 0.6152 0.4862 0.4606 0.074 Uiso 1 1 calc R . .
C7 C 0.36355(9) 0.0644(2) 0.5649(3) 0.0732(8) Uani 1 1 d . . .
H7A H 0.3404 -0.0141 0.5785 0.088 Uiso 1 1 calc R . .
H7B H 0.3892 0.0345 0.4984 0.088 Uiso 1 1 calc R . .
C5 C 0.34183(10) 0.2282(3) 0.3668(3) 0.0716(8) Uani 1 1 d . . .
H5 H 0.3660 0.1822 0.3124 0.086 Uiso 1 1 calc R . .
C6 C 0.31400(12) 0.3391(3) 0.3104(3) 0.0879(9) Uani 1 1 d . . .
H6 H 0.3195 0.3660 0.2184 0.106 Uiso 1 1 calc R . .
C3 C 0.29803(9) 0.2582(3) 0.5781(3) 0.0796(8) Uani 1 1 d . . .
H3 H 0.2918 0.2315 0.6699 0.096 Uiso 1 1 calc R . .
C2 C 0.27113(10) 0.3686(4) 0.5219(4) 0.0983(10) Uani 1 1 d . . .
H2 H 0.2474 0.4163 0.5762 0.118 Uiso 1 1 calc R . .
C1 C 0.27887(12) 0.4086(3) 0.3881(4) 0.0958(10) Uani 1 1 d . . .
H1A H 0.2604 0.4828 0.3499 0.115 Uiso 1 1 calc R . .
H1 H 0.3648(10) 0.117(3) 0.766(3) 0.128(13) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C9 C12 1.522(3) . ?
C9 C8 1.526(3) . ?
C9 C10 1.527(2) . ?
C9 H9 0.9800 . ?
N1 C7 1.465(3) . ?
N1 C8 1.483(2) . ?
N1 H1 0.931(17) . ?
C11 C12 1.390(3) 4_656 ?
C11 C16 1.397(3) 4_656 ?
C11 C8 1.520(3) . ?
C8 H8 0.9800 . ?
C12 C11 1.391(3) 4_656 ?
C12 C13 1.394(3) . ?
C13 C14 1.384(3) . ?
C13 H13 0.9300 . ?
C16 C15 1.374(3) . ?
C16 C11 1.396(3) 4_656 ?
C16 H16 0.9300 . ?
C10 C9 1.527(2) 4_656 ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C4 C5 1.371(3) . ?
C4 C3 1.378(3) . ?
C4 C7 1.515(3) . ?
C15 H15 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 C6 1.390(4) . ?
C5 H5 0.9300 . ?
C6 C1 1.357(4) . ?
C6 H6 0.9300 . ?
C3 C2 1.373(4) . ?
C3 H3 0.9300 . ?
C2 C1 1.354(4) . ?
C2 H2 0.9300 . ?
C1 H1A 0.9300 . ?

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
C12 C9 C8 111.59(15) . . ?
C12 C9 C10 111.18(15) . . ?
C8 C9 C10 109.23(15) . . ?
C12 C9 H9 108.2 . . ?
C8 C9 H9 108.2 . . ?
C10 C9 H9 108.2 . . ?
C7 N1 C8 114.04(19) . . ?
C7 N1 H1 110(2) . . ?
C8 N1 H1 114(2) . . ?
C12 C11 C16 119.23(19) 4_656 4_656 ?
C12 C11 C8 121.91(17) 4_656 . ?
C16 C11 C8 118.85(19) 4_656 . ?
N1 C8 C11 108.39(17) . . ?
N1 C8 C9 110.04(16) . . ?
C11 C8 C9 111.67(16) . . ?
N1 C8 H8 108.9 . . ?
C11 C8 H8 108.9 . . ?
C9 C8 H8 108.9 . . ?
C11 C12 C13 118.86(19) 4_656 . ?
C11 C12 C9 121.48(18) 4_656 . ?
C13 C12 C9 119.66(19) . . ?
C14 C13 C12 121.3(2) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C16 C11 121.0(2) . 4_656 ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 4_656 . ?
C9 C10 C9 107.4(2) . 4_656 ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10A 110.2 4_656 . ?
C9 C10 H10B 110.2 . . ?
C9 C10 H10B 110.2 4_656 . ?
H10A C10 H10B 108.5 . . ?
C15 C14 C13 119.5(2) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 121.5(2) . . ?
C3 C4 C7 121.1(2) . . ?
C16 C15 C14 120.1(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
N1 C7 C4 115.79(19) . . ?
N1 C7 H7A 108.3 . . ?
C4 C7 H7A 108.3 . . ?
N1 C7 H7B 108.3 . . ?
C4 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C4 C5 C6 120.6(3) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C2 C3 C4 121.6(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C2 C1 C6 119.1(3) . . ?
C2 C1 H1A 120.4 . . ?
C6 C1 H1A 120.4 . . ?

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
C7 N1 C8 C11 156.98(19) . . . . ?
C7 N1 C8 C9 -80.7(2) . . . . ?
C12 C11 C8 N1 106.8(2) 4_656 . . . ?
C16 C11 C8 N1 -73.3(2) 4_656 . . . ?
C12 C11 C8 C9 -14.6(2) 4_656 . . . ?
C16 C11 C8 C9 165.36(17) 4_656 . . . ?
C12 C9 C8 N1 165.13(17) . . . . ?
C10 C9 C8 N1 -71.5(2) . . . . ?
C12 C9 C8 C11 -74.5(2) . . . . ?
C10 C9 C8 C11 48.9(2) . . . . ?
C8 C9 C12 C11 101.9(2) . . . 4_656 ?
C10 C9 C12 C11 -20.3(2) . . . 4_656 ?
C8 C9 C12 C13 -77.5(2) . . . . ?
C10 C9 C12 C13 160.23(18) . . . . ?
C11 C12 C13 C14 1.1(3) 4_656 . . . ?
C9 C12 C13 C14 -179.48(18) . . . . ?
C12 C9 C10 C9 53.74(11) . . . 4_656 ?
C8 C9 C10 C9 -69.84(13) . . . 4_656 ?
C12 C13 C14 C15 -0.6(3) . . . . ?
C11 C16 C15 C14 1.3(3) 4_656 . . . ?
C13 C14 C15 C16 -0.6(3) . . . . ?
C8 N1 C7 C4 -67.3(3) . . . . ?
C5 C4 C7 N1 127.8(3) . . . . ?
C3 C4 C7 N1 -52.2(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C7 C4 C5 C6 179.5(2) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C7 C4 C3 C2 179.8(2) . . . . ?
C4 C3 C2 C1 0.8(5) . . . . ?
C3 C2 C1 C6 -0.7(5) . . . . ?
C5 C6 C1 C2 0.0(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 969972'
