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

#######################################################################
#
#                 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_bo1446

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 N2 S'
_chemical_formula_weight         280.38

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.241(2)
_cell_length_b                   9.610(3)
_cell_length_c                   9.790(3)
_cell_angle_alpha                87.334(9)
_cell_angle_beta                 71.536(8)
_cell_angle_gamma                84.334(9)
_cell_volume                     731.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    2544
_cell_measurement_theta_min      2.616
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.212
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8985
_exptl_absorpt_correction_T_max  0.9348
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7920
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0350
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         29.13
_reflns_number_total             3798
_reflns_number_gt                3235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0265P)²+0.3850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3798
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.83816(4) 0.25912(4) 0.79894(4) 0.02299(10) Uani 1 1 d . . .
N1 N 0.72606(18) 0.82214(15) 0.27479(14) 0.0347(3) Uani 1 1 d . . .
N2 N 0.2313(2) 1.06673(15) 0.37928(17) 0.0407(4) Uani 1 1 d . . .
C1 C 0.87063(19) 0.11265(14) 0.89607(15) 0.0242(3) Uani 1 1 d . . .
H1 H 0.9794 0.0617 0.8817 0.029 Uiso 1 1 calc R . .
C2 C 0.72388(18) 0.07736(14) 0.99592(15) 0.0239(3) Uani 1 1 d . . .
H2 H 0.7183 -0.0016 1.0587 0.029 Uiso 1 1 calc R . .
C3 C 0.57911(18) 0.17115(14) 0.99666(15) 0.0212(3) Uani 1 1 d . . .
H3 H 0.4665 0.1626 1.0607 0.025 Uiso 1 1 calc R . .
C4 C 0.62082(17) 0.27650(13) 0.89332(14) 0.0184(3) Uani 1 1 d . . .
C5 C 0.50222(17) 0.38400(13) 0.86219(14) 0.0194(3) Uani 1 1 d . . .
H5 H 0.3853 0.3844 0.9198 0.023 Uiso 1 1 calc R . .
C6 C 0.54182(17) 0.48421(13) 0.75873(14) 0.0193(3) Uani 1 1 d . . .
H6 H 0.6596 0.4886 0.7051 0.023 Uiso 1 1 calc R . .
C7 C 0.41880(17) 0.58531(13) 0.72333(14) 0.0179(3) Uani 1 1 d . . .
C8 C 0.23126(16) 0.58731(13) 0.80872(14) 0.0190(3) Uani 1 1 d . . .
H8A H 0.2129 0.6299 0.9032 0.023 Uiso 1 1 calc R . .
H8B H 0.2004 0.4897 0.8271 0.023 Uiso 1 1 calc R . .
C9 C 0.11000(16) 0.66739(13) 0.73577(14) 0.0182(3) Uani 1 1 d . . .
C10 C 0.18234(17) 0.80682(13) 0.67425(14) 0.0201(3) Uani 1 1 d . . .
H10A H 0.1080 0.8567 0.6223 0.024 Uiso 1 1 calc R . .
H10B H 0.1816 0.8664 0.7543 0.024 Uiso 1 1 calc R . .
C11 C 0.36180(17) 0.78343(13) 0.57352(14) 0.0181(3) Uani 1 1 d . . .
C12 C 0.47527(17) 0.67722(13) 0.61182(14) 0.0197(3) Uani 1 1 d . . .
H12 H 0.5938 0.6707 0.5577 0.024 Uiso 1 1 calc R . .
C13 C -0.06731(18) 0.69536(16) 0.84752(15) 0.0269(3) Uani 1 1 d . . .
H13A H -0.1126 0.6062 0.8862 0.032 Uiso 1 1 calc R . .
H13B H -0.1453 0.7475 0.8019 0.032 Uiso 1 1 calc R . .
H13C H -0.0576 0.7503 0.9260 0.032 Uiso 1 1 calc R . .
C14 C 0.0931(2) 0.58226(15) 0.61362(15) 0.0267(3) Uani 1 1 d . . .
H14A H 0.2067 0.5620 0.5428 0.032 Uiso 1 1 calc R . .
H14B H 0.0173 0.6359 0.5670 0.032 Uiso 1 1 calc R . .
H14C H 0.0446 0.4943 0.6528 0.032 Uiso 1 1 calc R . .
C15 C 0.41809(18) 0.86269(14) 0.44992(14) 0.0202(3) Uani 1 1 d . . .
C16 C 0.58948(19) 0.84005(14) 0.35318(15) 0.0238(3) Uani 1 1 d . . .
C17 C 0.3120(2) 0.97454(15) 0.41097(16) 0.0258(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.7087(14) . ?
S1 C4 1.7313(14) . ?
N1 C16 1.146(2) . ?
N2 C17 1.1457(19) . ?
C1 C2 1.354(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.4208(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3856(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.4406(18) . ?
C5 C6 1.3498(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4452(17) . ?
C6 H6 0.9500 . ?
C7 C12 1.3632(17) . ?
C7 C8 1.5051(19) . ?
C8 C9 1.5330(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.5289(19) . ?
C9 C13 1.5303(19) . ?
C9 C10 1.5391(18) . ?
C10 C11 1.4972(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.3741(17) . ?
C11 C12 1.4335(18) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.432(2) . ?
C15 C17 1.4325(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C4 91.87(7) . . ?
C2 C1 S1 112.41(11) . . ?
C2 C1 H1 123.8 . . ?
S1 C1 H1 123.8 . . ?
C1 C2 C3 112.79(12) . . ?
C1 C2 H2 123.6 . . ?
C3 C2 H2 123.6 . . ?
C4 C3 C2 112.31(12) . . ?
C4 C3 H3 123.8 . . ?
C2 C3 H3 123.8 . . ?
C3 C4 C5 125.98(12) . . ?
C3 C4 S1 110.62(10) . . ?
C5 C4 S1 123.37(10) . . ?
C6 C5 C4 126.06(13) . . ?
C6 C5 H5 117.0 . . ?
C4 C5 H5 117.0 . . ?
C5 C6 C7 125.00(13) . . ?
C5 C6 H6 117.5 . . ?
C7 C6 H6 117.5 . . ?
C12 C7 C6 119.05(12) . . ?
C12 C7 C8 121.04(12) . . ?
C6 C7 C8 119.91(11) . . ?
C7 C8 C9 114.51(10) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C14 C9 C13 109.01(12) . . ?
C14 C9 C8 110.69(11) . . ?
C13 C9 C8 108.97(11) . . ?
C14 C9 C10 109.26(11) . . ?
C13 C9 C10 109.89(11) . . ?
C8 C9 C10 109.01(11) . . ?
C11 C10 C9 111.20(11) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C15 C11 C12 120.72(13) . . ?
C15 C11 C10 121.51(12) . . ?
C12 C11 C10 117.76(11) . . ?
C7 C12 C11 122.22(13) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 121.57(12) . . ?
C11 C15 C17 122.69(13) . . ?
C16 C15 C17 115.73(12) . . ?
N1 C16 C15 179.40(15) . . ?
N2 C17 C15 177.82(16) . . ?

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
C4 S1 C1 C2 0.09(12) . . . . ?
S1 C1 C2 C3 -0.55(17) . . . . ?
C1 C2 C3 C4 0.87(18) . . . . ?
C2 C3 C4 C5 177.03(13) . . . . ?
C2 C3 C4 S1 -0.78(15) . . . . ?
C1 S1 C4 C3 0.41(11) . . . . ?
C1 S1 C4 C5 -177.47(12) . . . . ?
C3 C4 C5 C6 -177.90(14) . . . . ?
S1 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 C7 175.70(13) . . . . ?
C5 C6 C7 C12 -177.09(13) . . . . ?
C5 C6 C7 C8 2.5(2) . . . . ?
C12 C7 C8 C9 16.57(18) . . . . ?
C6 C7 C8 C9 -163.05(12) . . . . ?
C7 C8 C9 C14 75.29(14) . . . . ?
C7 C8 C9 C13 -164.85(11) . . . . ?
C7 C8 C9 C10 -44.91(15) . . . . ?
C14 C9 C10 C11 -65.12(14) . . . . ?
C13 C9 C10 C11 175.32(11) . . . . ?
C8 C9 C10 C11 55.95(14) . . . . ?
C9 C10 C11 C15 141.67(12) . . . . ?
C9 C10 C11 C12 -39.75(16) . . . . ?
C6 C7 C12 C11 -177.84(12) . . . . ?
C8 C7 C12 C11 2.5(2) . . . . ?
C15 C11 C12 C7 -171.65(13) . . . . ?
C10 C11 C12 C7 9.76(19) . . . . ?
C12 C11 C15 C16 1.7(2) . . . . ?
C10 C11 C15 C16 -179.74(12) . . . . ?
C12 C11 C15 C17 -176.79(13) . . . . ?
C10 C11 C15 C17 1.8(2) . . . . ?
C11 C15 C16 N1 141(15) . . . . ?
C17 C15 C16 N1 -40(15) . . . . ?
C11 C15 C17 N2 128(4) . . . . ?
C16 C15 C17 N2 -51(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.373
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.050
_database_code_depnum_ccdc_archive 'CCDC 994852'
#######################################################################
#
#                 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_bo2840

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H18 N2 S'
_chemical_formula_weight         294.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   9.1048(19)
_cell_length_b                   7.4536(15)
_cell_length_c                   23.795(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.952(4)
_cell_angle_gamma                90.00
_cell_volume                     1606.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5624
_cell_measurement_theta_min      2.490
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.59
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_type   Multi-scans
_exptl_absorpt_correction_T_min  0.8928
_exptl_absorpt_correction_T_max  0.9835
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            13835
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         29.13
_reflns_number_total             4250
_reflns_number_gt                3761
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0563P)²+0.6800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4250
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0590
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.27415(4) 0.22364(5) 0.586516(17) 0.02924(12) Uani 1 1 d . . .
N1 N 0.38078(19) 0.8860(2) 0.21901(6) 0.0449(4) Uani 1 1 d . . .
N2 N 0.5238(2) 0.3850(2) 0.30190(7) 0.0502(4) Uani 1 1 d . . .
C1 C 0.22100(18) 0.1656(2) 0.65183(7) 0.0307(3) Uani 1 1 d . . .
C2 C 0.14089(19) 0.3001(2) 0.67233(7) 0.0316(3) Uani 1 1 d . . .
H2 H 0.1015 0.2938 0.7077 0.038 Uiso 1 1 calc R . .
C3 C 0.12179(19) 0.4502(2) 0.63597(7) 0.0310(3) Uani 1 1 d . . .
H3 H 0.0677 0.5540 0.6444 0.037 Uiso 1 1 calc R . .
C4 C 0.18886(17) 0.4313(2) 0.58740(6) 0.0266(3) Uani 1 1 d . . .
C5 C 0.19331(17) 0.5606(2) 0.54257(7) 0.0280(3) Uani 1 1 d . . .
H5 H 0.1394 0.6686 0.5458 0.034 Uiso 1 1 calc R . .
C6 C 0.26655(17) 0.5432(2) 0.49650(6) 0.0275(3) Uani 1 1 d . . .
H6 H 0.3258 0.4391 0.4943 0.033 Uiso 1 1 calc R . .
C7 C 0.26281(17) 0.6690(2) 0.45023(6) 0.0259(3) Uani 1 1 d . . .
C8 C 0.18195(18) 0.8444(2) 0.45304(7) 0.0281(3) Uani 1 1 d . . .
H8A H 0.1977 0.8908 0.4922 0.034 Uiso 1 1 calc R . .
H8B H 0.0749 0.8223 0.4441 0.034 Uiso 1 1 calc R . .
C9 C 0.23008(16) 0.98843(19) 0.41273(6) 0.0238(3) Uani 1 1 d . . .
C10 C 0.23174(17) 0.9058(2) 0.35393(6) 0.0263(3) Uani 1 1 d . . .
H10A H 0.1290 0.8792 0.3383 0.032 Uiso 1 1 calc R . .
H10B H 0.2725 0.9944 0.3287 0.032 Uiso 1 1 calc R . .
C11 C 0.32122(16) 0.73696(19) 0.35427(6) 0.0241(3) Uani 1 1 d . . .
C12 C 0.32834(17) 0.6249(2) 0.40344(6) 0.0268(3) Uani 1 1 d . . .
H12 H 0.3812 0.5150 0.4033 0.032 Uiso 1 1 calc R . .
C13 C 0.11946(18) 1.1431(2) 0.41036(7) 0.0308(3) Uani 1 1 d . . .
H13A H 0.1501 1.2370 0.3852 0.037 Uiso 1 1 calc R . .
H13B H 0.1160 1.1924 0.4484 0.037 Uiso 1 1 calc R . .
H13C H 0.0213 1.0989 0.3960 0.037 Uiso 1 1 calc R . .
C14 C 0.38414(17) 1.0605(2) 0.43299(7) 0.0293(3) Uani 1 1 d . . .
H14A H 0.4555 0.9616 0.4352 0.035 Uiso 1 1 calc R . .
H14B H 0.3828 1.1149 0.4704 0.035 Uiso 1 1 calc R . .
H14C H 0.4127 1.1510 0.4063 0.035 Uiso 1 1 calc R . .
C15 C 0.38933(17) 0.6874(2) 0.30795(6) 0.0261(3) Uani 1 1 d . . .
C16 C 0.38391(18) 0.7969(2) 0.25859(7) 0.0308(3) Uani 1 1 d . . .
C17 C 0.46508(19) 0.5197(2) 0.30508(7) 0.0326(4) Uani 1 1 d . . .
C18 C 0.2653(2) -0.0109(3) 0.67818(8) 0.0429(4) Uani 1 1 d . . .
H18A H 0.3228 -0.0787 0.6528 0.051 Uiso 0.50 1 calc PR . .
H18B H 0.1767 -0.0791 0.6848 0.051 Uiso 0.50 1 calc PR . .
H18C H 0.3254 0.0093 0.7142 0.051 Uiso 0.50 1 calc PR . .
H18D H 0.2271 -0.0203 0.7151 0.051 Uiso 0.50 1 calc PR . .
H18E H 0.3732 -0.0199 0.6831 0.051 Uiso 0.50 1 calc PR . .
H18F H 0.2245 -0.1083 0.6537 0.051 Uiso 0.50 1 calc PR . .


_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
S1 C1 1.7298(17) . ?
S1 C4 1.7330(16) . ?
N1 C16 1.150(2) . ?
N2 C17 1.143(2) . ?
C1 C2 1.359(2) . ?
C1 C18 1.495(2) . ?
C2 C3 1.414(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.369(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.441(2) . ?
C5 C6 1.347(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(2) . ?
C6 H6 0.9500 . ?
C7 C12 1.357(2) . ?
C7 C8 1.505(2) . ?
C8 C9 1.534(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.528(2) . ?
C9 C10 1.530(2) . ?
C9 C14 1.532(2) . ?
C10 C11 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C15 1.370(2) . ?
C11 C12 1.434(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.427(2) . ?
C15 C17 1.433(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18D 0.9800 . ?
C18 H18E 0.9800 . ?
C18 H18F 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
C1 S1 C4 92.57(8) . . ?
C2 C1 C18 129.03(16) . . ?
C2 C1 S1 110.41(12) . . ?
C18 C1 S1 120.55(14) . . ?
C1 C2 C3 113.59(15) . . ?
C1 C2 H2 123.2 . . ?
C3 C2 H2 123.2 . . ?
C4 C3 C2 113.44(15) . . ?
C4 C3 H3 123.3 . . ?
C2 C3 H3 123.3 . . ?
C3 C4 C5 127.25(14) . . ?
C3 C4 S1 109.98(12) . . ?
C5 C4 S1 122.77(12) . . ?
C6 C5 C4 126.31(14) . . ?
C6 C5 H5 116.8 . . ?
C4 C5 H5 116.8 . . ?
C5 C6 C7 125.69(14) . . ?
C5 C6 H6 117.2 . . ?
C7 C6 H6 117.2 . . ?
C12 C7 C6 119.37(14) . . ?
C12 C7 C8 120.38(14) . . ?
C6 C7 C8 120.21(13) . . ?
C7 C8 C9 114.04(12) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C13 C9 C10 109.80(12) . . ?
C13 C9 C14 109.01(13) . . ?
C10 C9 C14 109.46(12) . . ?
C13 C9 C8 108.73(12) . . ?
C10 C9 C8 108.71(12) . . ?
C14 C9 C8 111.12(12) . . ?
C11 C10 C9 112.93(12) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C15 C11 C12 120.90(14) . . ?
C15 C11 C10 120.86(14) . . ?
C12 C11 C10 118.19(13) . . ?
C7 C12 C11 122.80(14) . . ?
C7 C12 H12 118.6 . . ?
C11 C12 H12 118.6 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 C16 121.88(14) . . ?
C11 C15 C17 122.25(14) . . ?
C16 C15 C17 115.82(14) . . ?
N1 C16 C15 179.3(2) . . ?
N2 C17 C15 178.7(2) . . ?
C1 C18 H18A 109.5 . . ?
C1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 C18 H18D 109.5 . . ?
H18A C18 H18D 141.1 . . ?
H18B C18 H18D 56.3 . . ?
H18C C18 H18D 56.3 . . ?
C1 C18 H18E 109.5 . . ?
H18A C18 H18E 56.3 . . ?
H18B C18 H18E 141.1 . . ?
H18C C18 H18E 56.3 . . ?
H18D C18 H18E 109.5 . . ?
C1 C18 H18F 109.5 . . ?
H18A C18 H18F 56.3 . . ?
H18B C18 H18F 56.3 . . ?
H18C C18 H18F 141.1 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 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
C4 S1 C1 C2 0.50(13) . . . . ?
C4 S1 C1 C18 -178.83(14) . . . . ?
C18 C1 C2 C3 179.16(16) . . . . ?
S1 C1 C2 C3 -0.09(19) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C2 C3 C4 C5 -178.40(16) . . . . ?
C2 C3 C4 S1 0.87(19) . . . . ?
C1 S1 C4 C3 -0.78(13) . . . . ?
C1 S1 C4 C5 178.53(14) . . . . ?
C3 C4 C5 C6 176.22(17) . . . . ?
S1 C4 C5 C6 -3.0(3) . . . . ?
C4 C5 C6 C7 176.01(15) . . . . ?
C5 C6 C7 C12 -172.45(16) . . . . ?
C5 C6 C7 C8 5.2(3) . . . . ?
C12 C7 C8 C9 -22.5(2) . . . . ?
C6 C7 C8 C9 159.85(14) . . . . ?
C7 C8 C9 C13 168.11(13) . . . . ?
C7 C8 C9 C10 48.61(17) . . . . ?
C7 C8 C9 C14 -71.92(17) . . . . ?
C13 C9 C10 C11 -171.75(13) . . . . ?
C14 C9 C10 C11 68.62(16) . . . . ?
C8 C9 C10 C11 -52.92(16) . . . . ?
C9 C10 C11 C15 -151.12(14) . . . . ?
C9 C10 C11 C12 31.52(19) . . . . ?
C6 C7 C12 C11 175.78(14) . . . . ?
C8 C7 C12 C11 -1.9(2) . . . . ?
C15 C11 C12 C7 179.84(15) . . . . ?
C10 C11 C12 C7 -2.8(2) . . . . ?
C12 C11 C15 C16 -179.91(15) . . . . ?
C10 C11 C15 C16 2.8(2) . . . . ?
C12 C11 C15 C17 2.7(2) . . . . ?
C10 C11 C15 C17 -174.58(14) . . . . ?
C11 C15 C16 N1 90(18) . . . . ?
C17 C15 C16 N1 -92(18) . . . . ?
C11 C15 C17 N2 121(10) . . . . ?
C16 C15 C17 N2 -57(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.046
_database_code_depnum_ccdc_archive 'CCDC 994853'
#######################################################################
#
#                 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_bo2806

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.45

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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   5.9539(12)
_cell_length_b                   7.3758(15)
_cell_length_c                   22.019(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.787(3)
_cell_angle_gamma                90.00
_cell_volume                     966.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    3375
_cell_measurement_theta_min      2.762
_cell_measurement_theta_max      29.123

_exptl_crystal_description       Platelet
_exptl_crystal_colour            Orange
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             372
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9982
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8636
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         29.11
_reflns_number_total             2744
_reflns_number_gt                2339
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.0560P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_number_reflns         2744
_refine_ls_number_parameters     246
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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
N1 N 1.0541(4) 0.7032(3) 0.78110(9) 0.0508(5) Uani 1 1 d . . .
N2 N 1.1016(3) 0.5257(4) 0.96871(8) 0.0506(5) Uani 1 1 d . . .
C1 C -0.5260(3) 0.1294(3) 0.45674(8) 0.0249(4) Uani 1 1 d . . .
H1 H -0.6050 0.0785 0.4895 0.030 Uiso 1 1 calc R . .
C2 C -0.6242(3) 0.1266(3) 0.39869(8) 0.0271(4) Uani 1 1 d . . .
H2 H -0.7687 0.0742 0.3922 0.033 Uiso 1 1 calc R . .
C3 C -0.5116(3) 0.2001(3) 0.35013(8) 0.0276(4) Uani 1 1 d . . .
H3 H -0.5786 0.1985 0.3104 0.033 Uiso 1 1 calc R . .
C4 C -0.3010(3) 0.2757(3) 0.36016(8) 0.0294(4) Uani 1 1 d . . .
H4 H -0.2226 0.3254 0.3271 0.035 Uiso 1 1 calc R . .
C5 C -0.2042(3) 0.2792(3) 0.41824(8) 0.0253(4) Uani 1 1 d . . .
H5 H -0.0602 0.3329 0.4245 0.030 Uiso 1 1 calc R . .
C6 C -0.3137(3) 0.2053(2) 0.46809(7) 0.0201(3) Uani 1 1 d . . .
C7 C -0.2056(3) 0.2058(2) 0.53013(7) 0.0199(3) Uani 1 1 d . . .
C8 C 0.0024(3) 0.2911(2) 0.54136(8) 0.0231(4) Uani 1 1 d . . .
H8 H 0.0737 0.3505 0.5089 0.028 Uiso 1 1 calc R . .
C9 C 0.1063(3) 0.2910(3) 0.59829(8) 0.0236(4) Uani 1 1 d . . .
H9 H 0.2466 0.3507 0.6042 0.028 Uiso 1 1 calc R . .
C10 C 0.0081(3) 0.2041(2) 0.64768(7) 0.0214(3) Uani 1 1 d . . .
C11 C -0.2002(3) 0.1206(3) 0.63677(8) 0.0245(4) Uani 1 1 d . . .
H11 H -0.2718 0.0621 0.6694 0.029 Uiso 1 1 calc R . .
C12 C -0.3050(3) 0.1209(3) 0.57970(8) 0.0234(3) Uani 1 1 d . . .
H12 H -0.4465 0.0626 0.5740 0.028 Uiso 1 1 calc R . .
C13 C 0.1167(3) 0.1946(3) 0.70806(8) 0.0248(4) Uani 1 1 d . . .
H13 H 0.0456 0.1235 0.7379 0.030 Uiso 1 1 calc R . .
C14 C 0.3094(3) 0.2786(3) 0.72464(8) 0.0268(4) Uani 1 1 d . . .
H14 H 0.3799 0.3498 0.6947 0.032 Uiso 1 1 calc R . .
C15 C 0.4183(3) 0.2698(2) 0.78434(8) 0.0245(4) Uani 1 1 d . . .
C16 C 0.6023(3) 0.3759(3) 0.79575(8) 0.0274(4) Uani 1 1 d . . .
H16 H 0.6600 0.4456 0.7635 0.033 Uiso 1 1 calc R . .
C17 C 0.7122(3) 0.3866(3) 0.85456(8) 0.0253(4) Uani 1 1 d . . .
C18 C 0.6159(3) 0.2794(3) 0.90528(8) 0.0291(4) Uani 1 1 d . . .
H18A H 0.5051 0.3553 0.9262 0.035 Uiso 1 1 calc R . .
H18B H 0.7379 0.2490 0.9351 0.035 Uiso 1 1 calc R . .
C19 C 0.5009(3) 0.1036(3) 0.88379(8) 0.0281(4) Uani 1 1 d . . .
C20 C 0.3287(3) 0.1485(3) 0.83269(8) 0.0266(4) Uani 1 1 d . . .
H20A H 0.2761 0.0340 0.8136 0.032 Uiso 1 1 calc R . .
H20B H 0.1972 0.2080 0.8506 0.032 Uiso 1 1 calc R . .
C21 C 0.6755(4) -0.0306(3) 0.86088(10) 0.0397(5) Uani 1 1 d . . .
H21A H 0.6008 -0.1442 0.8490 0.048 Uiso 1 1 calc R . .
H21B H 0.7881 -0.0548 0.8933 0.048 Uiso 1 1 calc R . .
H21C H 0.7492 0.0212 0.8257 0.048 Uiso 1 1 calc R . .
C22 C 0.3787(4) 0.0190(4) 0.93682(9) 0.0458(6) Uani 1 1 d . . .
H22A H 0.4882 -0.0131 0.9692 0.055 Uiso 1 1 calc R . .
H22B H 0.2992 -0.0903 0.9229 0.055 Uiso 1 1 calc R . .
H22C H 0.2705 0.1062 0.9524 0.055 Uiso 1 1 calc R . .
C23 C 0.8940(3) 0.4981(3) 0.86431(8) 0.0275(4) Uani 1 1 d . . .
C24 C 0.9827(3) 0.6106(3) 0.81766(9) 0.0335(4) Uani 1 1 d . . .
C25 C 1.0071(3) 0.5129(3) 0.92275(9) 0.0329(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C24 1.147(3) . ?
N2 C25 1.146(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.398(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.492(2) . ?
C7 C8 1.404(2) . ?
C7 C12 1.405(2) . ?
C8 C9 1.380(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.405(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(2) . ?
C10 C13 1.462(2) . ?
C11 C12 1.386(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.345(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.449(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.363(3) . ?
C15 C20 1.501(2) . ?
C16 C17 1.435(2) . ?
C16 H16 0.9500 . ?
C17 C23 1.370(2) . ?
C17 C18 1.497(3) . ?
C18 C19 1.534(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C22 1.528(3) . ?
C19 C21 1.532(3) . ?
C19 C20 1.535(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.434(3) . ?
C23 C25 1.438(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.52(17) . . ?
C2 C1 H1 119.2 . . ?
C6 C1 H1 119.2 . . ?
C1 C2 C3 120.18(17) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.41(17) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.23(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.59(17) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.07(15) . . ?
C1 C6 C7 121.77(15) . . ?
C5 C6 C7 121.16(15) . . ?
C8 C7 C12 116.97(15) . . ?
C8 C7 C6 121.02(14) . . ?
C12 C7 C6 122.02(14) . . ?
C9 C8 C7 121.84(16) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 121.17(16) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 117.12(15) . . ?
C11 C10 C13 119.98(16) . . ?
C9 C10 C13 122.88(15) . . ?
C12 C11 C10 121.82(16) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C7 121.08(16) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C14 C13 C10 125.04(16) . . ?
C14 C13 H13 117.5 . . ?
C10 C13 H13 117.5 . . ?
C13 C14 C15 125.42(17) . . ?
C13 C14 H14 117.3 . . ?
C15 C14 H14 117.3 . . ?
C16 C15 C14 118.40(17) . . ?
C16 C15 C20 120.85(16) . . ?
C14 C15 C20 120.75(16) . . ?
C15 C16 C17 122.63(17) . . ?
C15 C16 H16 118.7 . . ?
C17 C16 H16 118.7 . . ?
C23 C17 C16 120.68(16) . . ?
C23 C17 C18 121.27(15) . . ?
C16 C17 C18 117.99(16) . . ?
C17 C18 C19 113.22(15) . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C22 C19 C21 109.39(18) . . ?
C22 C19 C18 109.14(17) . . ?
C21 C19 C18 110.32(16) . . ?
C22 C19 C20 108.98(15) . . ?
C21 C19 C20 110.05(16) . . ?
C18 C19 C20 108.95(15) . . ?
C15 C20 C19 113.86(15) . . ?
C15 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C15 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 C24 122.79(16) . . ?
C17 C23 C25 122.10(17) . . ?
C24 C23 C25 115.10(17) . . ?
N1 C24 C23 178.7(2) . . ?
N2 C25 C23 178.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.0(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
C2 C1 C6 C7 -178.90(16) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.52(16) . . . . ?
C1 C6 C7 C8 -176.60(18) . . . . ?
C5 C6 C7 C8 4.3(2) . . . . ?
C1 C6 C7 C12 3.8(2) . . . . ?
C5 C6 C7 C12 -175.24(19) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C6 C7 C8 C9 -179.17(16) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C11 -1.0(3) . . . . ?
C8 C9 C10 C13 177.48(17) . . . . ?
C9 C10 C11 C12 0.8(3) . . . . ?
C13 C10 C11 C12 -177.66(17) . . . . ?
C10 C11 C12 C7 -0.1(3) . . . . ?
C8 C7 C12 C11 -0.6(3) . . . . ?
C6 C7 C12 C11 179.03(16) . . . . ?
C11 C10 C13 C14 -175.73(18) . . . . ?
C9 C10 C13 C14 5.9(3) . . . . ?
C10 C13 C14 C15 -179.90(17) . . . . ?
C13 C14 C15 C16 -174.09(19) . . . . ?
C13 C14 C15 C20 5.1(3) . . . . ?
C14 C15 C16 C17 175.44(17) . . . . ?
C20 C15 C16 C17 -3.7(3) . . . . ?
C15 C16 C17 C23 -178.64(18) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C23 C17 C18 C19 -151.91(17) . . . . ?
C16 C17 C18 C19 30.9(2) . . . . ?
C17 C18 C19 C22 -171.64(16) . . . . ?
C17 C18 C19 C21 68.2(2) . . . . ?
C17 C18 C19 C20 -52.8(2) . . . . ?
C16 C15 C20 C19 -21.0(3) . . . . ?
C14 C15 C20 C19 159.86(17) . . . . ?
C22 C19 C20 C15 166.78(18) . . . . ?
C21 C19 C20 C15 -73.3(2) . . . . ?
C18 C19 C20 C15 47.8(2) . . . . ?
C16 C17 C23 C24 0.8(3) . . . . ?
C18 C17 C23 C24 -176.30(19) . . . . ?
C16 C17 C23 C25 179.57(18) . . . . ?
C18 C17 C23 C25 2.4(3) . . . . ?
C17 C23 C24 N1 137(11) . . . . ?
C25 C23 C24 N1 -42(11) . . . . ?
C17 C23 C25 N2 152(9) . . . . ?
C24 C23 C25 N2 -29(10) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.038
_database_code_depnum_ccdc_archive 'CCDC 994854'
#######################################################################
#
#                 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_bo2839

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H26 N2'
_chemical_formula_weight         330.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.7434(13)
_cell_length_b                   13.538(2)
_cell_length_c                   17.321(3)
_cell_angle_alpha                88.079(5)
_cell_angle_beta                 84.857(5)
_cell_angle_gamma                77.108(5)
_cell_volume                     1990.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    5733
_cell_measurement_theta_min      1.956
_cell_measurement_theta_max      29.127

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            21815
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0493
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         28.00
_reflns_number_total             9463
_reflns_number_gt                7284
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+0.6900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9463
_refine_ls_number_parameters     461
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1395
_refine_ls_wR_factor_gt          0.1246
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.15562(18) 0.38008(13) 1.02421(11) 0.0516(5) Uani 1 1 d . . .
N2 N 1.1217(2) 0.06449(12) 1.07028(11) 0.0508(4) Uani 1 1 d . . .
N3 N -0.1515(2) 0.75986(17) 0.73429(11) 0.0645(6) Uani 1 1 d . . .
N4 N -0.33441(19) 0.85368(14) 0.50707(11) 0.0564(5) Uani 1 1 d . . .
C1 C 0.31379(19) 0.83601(12) 0.78415(9) 0.0293(3) Uani 1 1 d . . .
C2 C 0.47028(19) 0.79491(12) 0.80004(10) 0.0319(4) Uani 1 1 d . . .
H2 H 0.5463 0.8352 0.7904 0.038 Uiso 1 1 calc R . .
C3 C 0.51645(18) 0.69800(12) 0.82914(9) 0.0293(3) Uani 1 1 d . . .
H3 H 0.6236 0.6725 0.8386 0.035 Uiso 1 1 calc R . .
C4 C 0.40799(17) 0.63612(11) 0.84513(9) 0.0254(3) Uani 1 1 d . . .
C5 C 0.25289(18) 0.67616(12) 0.82842(9) 0.0270(3) Uani 1 1 d . . .
H5 H 0.1771 0.6357 0.8374 0.032 Uiso 1 1 calc R . .
C6 C 0.20708(18) 0.77397(12) 0.79894(9) 0.0287(3) Uani 1 1 d . . .
H6 H 0.1003 0.7991 0.7886 0.034 Uiso 1 1 calc R . .
C7 C 0.45207(17) 0.53351(12) 0.87780(9) 0.0256(3) Uani 1 1 d . . .
H7 H 0.3745 0.4939 0.8822 0.031 Uiso 1 1 calc R . .
C8 C 0.59414(17) 0.49119(11) 0.90203(9) 0.0258(3) Uani 1 1 d . . .
H8 H 0.6697 0.5322 0.8982 0.031 Uiso 1 1 calc R . .
C9 C 0.64393(17) 0.39008(11) 0.93322(9) 0.0238(3) Uani 1 1 d . . .
C10 C 0.79100(17) 0.36214(11) 0.95790(9) 0.0250(3) Uani 1 1 d . . .
H10 H 0.8548 0.4107 0.9553 0.030 Uiso 1 1 calc R . .
C11 C 0.85386(17) 0.26322(11) 0.98750(9) 0.0247(3) Uani 1 1 d . . .
C12 C 0.75353(18) 0.18645(12) 0.99253(9) 0.0262(3) Uani 1 1 d . . .
H12A H 0.7020 0.1862 1.0458 0.031 Uiso 1 1 calc R . .
H12B H 0.8222 0.1185 0.9832 0.031 Uiso 1 1 calc R . .
C13 C 0.62602(18) 0.20542(12) 0.93489(9) 0.0273(3) Uani 1 1 d . . .
C14 C 0.53749(18) 0.31674(12) 0.93965(10) 0.0278(3) Uani 1 1 d . . .
H14A H 0.4658 0.3315 0.8976 0.033 Uiso 1 1 calc R . .
H14B H 0.4720 0.3272 0.9896 0.033 Uiso 1 1 calc R . .
C15 C 0.7006(2) 0.18117(13) 0.85234(10) 0.0383(4) Uani 1 1 d . . .
H15A H 0.7574 0.1101 0.8501 0.046 Uiso 1 1 calc R . .
H15B H 0.7742 0.2250 0.8378 0.046 Uiso 1 1 calc R . .
H15C H 0.6179 0.1929 0.8163 0.046 Uiso 1 1 calc R . .
C16 C 0.5108(2) 0.13740(13) 0.95770(11) 0.0381(4) Uani 1 1 d . . .
H16A H 0.4664 0.1512 1.0112 0.046 Uiso 1 1 calc R . .
H16B H 0.5664 0.0662 0.9535 0.046 Uiso 1 1 calc R . .
H16C H 0.4258 0.1512 0.9230 0.046 Uiso 1 1 calc R . .
C17 C 1.00053(18) 0.24068(12) 1.01437(9) 0.0284(3) Uani 1 1 d . . .
C18 C 1.08892(18) 0.31680(13) 1.01964(10) 0.0338(4) Uani 1 1 d . . .
C19 C 1.06814(19) 0.14261(13) 1.04500(10) 0.0347(4) Uani 1 1 d . . .
C20 C 0.2671(2) 0.94541(13) 0.75455(10) 0.0366(4) Uani 1 1 d . . .
C21 C 0.1039(2) 0.96941(15) 0.72466(13) 0.0527(5) Uani 1 1 d . . .
H21A H 0.1007 0.9221 0.6835 0.063 Uiso 1 1 calc R . .
H21B H 0.0810 1.0389 0.7040 0.063 Uiso 1 1 calc R . .
H21C H 0.0251 0.9626 0.7673 0.063 Uiso 1 1 calc R . .
C22 C 0.3840(3) 0.96422(17) 0.68766(13) 0.0571(6) Uani 1 1 d . . .
H22A H 0.4871 0.9604 0.7071 0.069 Uiso 1 1 calc R . .
H22B H 0.3464 1.0316 0.6650 0.069 Uiso 1 1 calc R . .
H22C H 0.3936 0.9127 0.6480 0.069 Uiso 1 1 calc R . .
C23 C 0.2669(3) 1.01536(15) 0.82180(13) 0.0641(7) Uani 1 1 d . . .
H23A H 0.1911 1.0027 0.8641 0.077 Uiso 1 1 calc R . .
H23B H 0.2372 1.0861 0.8043 0.077 Uiso 1 1 calc R . .
H23C H 0.3724 1.0023 0.8403 0.077 Uiso 1 1 calc R . .
C24 C 1.00967(18) 0.43828(12) 0.69224(9) 0.0285(3) Uani 1 1 d . . .
C25 C 0.85750(19) 0.44768(13) 0.72727(10) 0.0333(4) Uani 1 1 d . . .
H25 H 0.8432 0.4166 0.7766 0.040 Uiso 1 1 calc R . .
C26 C 0.72636(19) 0.50068(13) 0.69275(10) 0.0333(4) Uani 1 1 d . . .
H26 H 0.6246 0.5051 0.7186 0.040 Uiso 1 1 calc R . .
C27 C 0.74153(18) 0.54774(12) 0.62038(9) 0.0291(3) Uani 1 1 d . . .
C28 C 0.89351(19) 0.53883(13) 0.58533(10) 0.0337(4) Uani 1 1 d . . .
H28 H 0.9080 0.5697 0.5360 0.040 Uiso 1 1 calc R . .
C29 C 1.02382(19) 0.48620(14) 0.62044(10) 0.0347(4) Uani 1 1 d . . .
H29 H 1.1257 0.4826 0.5949 0.042 Uiso 1 1 calc R . .
C30 C 0.60947(19) 0.60435(13) 0.57942(10) 0.0318(4) Uani 1 1 d . . .
H30 H 0.6331 0.6196 0.5264 0.038 Uiso 1 1 calc R . .
C31 C 0.45931(19) 0.63745(13) 0.60729(10) 0.0318(4) Uani 1 1 d . . .
H31 H 0.4330 0.6259 0.6607 0.038 Uiso 1 1 calc R . .
C32 C 0.33418(18) 0.68977(12) 0.56135(9) 0.0294(3) Uani 1 1 d . . .
C33 C 0.18415(19) 0.71343(13) 0.59453(10) 0.0330(4) Uani 1 1 d . . .
H33 H 0.1656 0.6999 0.6483 0.040 Uiso 1 1 calc R . .
C34 C 0.05242(19) 0.75814(13) 0.55137(10) 0.0329(4) Uani 1 1 d . . .
C35 C 0.08269(19) 0.76937(14) 0.46532(10) 0.0350(4) Uani 1 1 d . . .
H35A H -0.0020 0.8232 0.4459 0.042 Uiso 1 1 calc R . .
H35B H 0.0800 0.7051 0.4404 0.042 Uiso 1 1 calc R . .
C36 C 0.24220(19) 0.79624(13) 0.44267(10) 0.0320(4) Uani 1 1 d . . .
C37 C 0.37059(19) 0.71522(13) 0.47741(9) 0.0323(4) Uani 1 1 d . . .
H37A H 0.3875 0.6526 0.4469 0.039 Uiso 1 1 calc R . .
H37B H 0.4702 0.7390 0.4722 0.039 Uiso 1 1 calc R . .
C38 C 0.2736(2) 0.79640(16) 0.35443(10) 0.0433(5) Uani 1 1 d . . .
H38A H 0.3779 0.8102 0.3402 0.052 Uiso 1 1 calc R . .
H38B H 0.1932 0.8490 0.3319 0.052 Uiso 1 1 calc R . .
H38C H 0.2697 0.7301 0.3347 0.052 Uiso 1 1 calc R . .
C39 C 0.2413(2) 0.90144(14) 0.47277(11) 0.0406(4) Uani 1 1 d . . .
H39A H 0.2181 0.9023 0.5292 0.049 Uiso 1 1 calc R . .
H39B H 0.1606 0.9522 0.4487 0.049 Uiso 1 1 calc R . .
H39C H 0.3448 0.9172 0.4597 0.049 Uiso 1 1 calc R . .
C40 C -0.09674(19) 0.78511(14) 0.58714(11) 0.0374(4) Uani 1 1 d . . .
C41 C -0.1287(2) 0.77111(17) 0.66860(13) 0.0466(5) Uani 1 1 d . . .
C42 C -0.2297(2) 0.82411(15) 0.54313(12) 0.0424(4) Uani 1 1 d . . .
C43 C 1.15517(19) 0.37461(13) 0.72698(10) 0.0319(4) Uani 1 1 d . . .
C44 C 1.2961(2) 0.42476(15) 0.71317(11) 0.0409(4) Uani 1 1 d . . .
H44A H 1.3246 0.4293 0.6574 0.049 Uiso 1 1 calc R . .
H44B H 1.3857 0.3841 0.7384 0.049 Uiso 1 1 calc R . .
H44C H 1.2682 0.4930 0.7349 0.049 Uiso 1 1 calc R . .
C45 C 1.1260(2) 0.3576(2) 0.81398(12) 0.0575(6) Uani 1 1 d . . .
H45A H 1.0915 0.4232 0.8397 0.069 Uiso 1 1 calc R . .
H45B H 1.2236 0.3201 0.8345 0.069 Uiso 1 1 calc R . .
H45C H 1.0443 0.3185 0.8238 0.069 Uiso 1 1 calc R . .
C46 C 1.1995(2) 0.27168(14) 0.68642(14) 0.0539(6) Uani 1 1 d . . .
H46A H 1.1129 0.2366 0.6961 0.065 Uiso 1 1 calc R . .
H46B H 1.2947 0.2305 0.7068 0.065 Uiso 1 1 calc R . .
H46C H 1.2193 0.2824 0.6305 0.065 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
N1 C18 1.147(2) . ?
N2 C19 1.146(2) . ?
N3 C41 1.148(3) . ?
N4 C42 1.145(2) . ?
C1 C6 1.391(2) . ?
C1 C2 1.405(2) . ?
C1 C20 1.530(2) . ?
C2 C3 1.376(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(2) . ?
C4 C7 1.465(2) . ?
C5 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.344(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.443(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.360(2) . ?
C9 C14 1.500(2) . ?
C10 C11 1.426(2) . ?
C10 H10 0.9500 . ?
C11 C17 1.370(2) . ?
C11 C12 1.498(2) . ?
C12 C13 1.536(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C16 1.529(2) . ?
C13 C15 1.532(2) . ?
C13 C14 1.534(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.429(2) . ?
C17 C19 1.433(2) . ?
C20 C21 1.524(3) . ?
C20 C23 1.525(3) . ?
C20 C22 1.529(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C29 1.392(2) . ?
C24 C25 1.393(2) . ?
C24 C43 1.529(2) . ?
C25 C26 1.383(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.396(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.392(2) . ?
C27 C30 1.463(2) . ?
C28 C29 1.382(2) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 C31 1.340(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.451(2) . ?
C31 H31 0.9500 . ?
C32 C33 1.358(2) . ?
C32 C37 1.505(2) . ?
C33 C34 1.437(2) . ?
C33 H33 0.9500 . ?
C34 C40 1.370(2) . ?
C34 C35 1.499(2) . ?
C35 C36 1.533(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C38 1.528(2) . ?
C36 C39 1.531(2) . ?
C36 C37 1.534(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.428(3) . ?
C40 C42 1.438(2) . ?
C43 C45 1.524(2) . ?
C43 C44 1.532(2) . ?
C43 C46 1.537(3) . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 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
C6 C1 C2 116.87(15) . . ?
C6 C1 C20 123.21(14) . . ?
C2 C1 C20 119.89(15) . . ?
C3 C2 C1 121.85(16) . . ?
C3 C2 H2 119.1 . . ?
C1 C2 H2 119.1 . . ?
C2 C3 C4 121.14(14) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.17(14) . . ?
C5 C4 C7 120.17(14) . . ?
C3 C4 C7 122.66(13) . . ?
C6 C5 C4 121.39(15) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C1 121.55(14) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
C8 C7 C4 124.83(14) . . ?
C8 C7 H7 117.6 . . ?
C4 C7 H7 117.6 . . ?
C7 C8 C9 126.86(14) . . ?
C7 C8 H8 116.6 . . ?
C9 C8 H8 116.6 . . ?
C10 C9 C8 118.34(14) . . ?
C10 C9 C14 119.94(14) . . ?
C8 C9 C14 121.72(13) . . ?
C9 C10 C11 122.99(14) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 H10 118.5 . . ?
C17 C11 C10 120.34(14) . . ?
C17 C11 C12 120.72(14) . . ?
C10 C11 C12 118.86(13) . . ?
C11 C12 C13 114.04(13) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C16 C13 C15 109.65(14) . . ?
C16 C13 C14 109.23(13) . . ?
C15 C13 C14 110.18(13) . . ?
C16 C13 C12 108.58(13) . . ?
C15 C13 C12 110.36(13) . . ?
C14 C13 C12 108.81(12) . . ?
C9 C14 C13 113.56(12) . . ?
C9 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C9 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 C18 121.37(14) . . ?
C11 C17 C19 122.32(15) . . ?
C18 C17 C19 116.08(14) . . ?
N1 C18 C17 177.90(18) . . ?
N2 C19 C17 179.3(2) . . ?
C21 C20 C23 108.76(17) . . ?
C21 C20 C22 107.48(16) . . ?
C23 C20 C22 110.42(19) . . ?
C21 C20 C1 112.22(15) . . ?
C23 C20 C1 107.91(14) . . ?
C22 C20 C1 110.05(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 116.43(15) . . ?
C29 C24 C43 120.38(15) . . ?
C25 C24 C43 123.11(15) . . ?
C26 C25 C24 122.30(16) . . ?
C26 C25 H25 118.8 . . ?
C24 C25 H25 118.8 . . ?
C25 C26 C27 120.89(15) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 116.97(15) . . ?
C28 C27 C30 118.52(15) . . ?
C26 C27 C30 124.51(15) . . ?
C29 C28 C27 121.72(16) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C24 121.68(16) . . ?
C28 C29 H29 119.2 . . ?
C24 C29 H29 119.2 . . ?
C31 C30 C27 128.20(16) . . ?
C31 C30 H30 115.9 . . ?
C27 C30 H30 115.9 . . ?
C30 C31 C32 124.41(16) . . ?
C30 C31 H31 117.8 . . ?
C32 C31 H31 117.8 . . ?
C33 C32 C31 119.22(15) . . ?
C33 C32 C37 120.67(14) . . ?
C31 C32 C37 120.10(14) . . ?
C32 C33 C34 122.48(16) . . ?
C32 C33 H33 118.8 . . ?
C34 C33 H33 118.8 . . ?
C40 C34 C33 121.11(16) . . ?
C40 C34 C35 121.15(15) . . ?
C33 C34 C35 117.67(15) . . ?
C34 C35 C36 112.04(13) . . ?
C34 C35 H35A 109.2 . . ?
C36 C35 H35A 109.2 . . ?
C34 C35 H35B 109.2 . . ?
C36 C35 H35B 109.2 . . ?
H35A C35 H35B 107.9 . . ?
C38 C36 C39 109.15(15) . . ?
C38 C36 C35 109.62(14) . . ?
C39 C36 C35 109.89(14) . . ?
C38 C36 C37 109.00(14) . . ?
C39 C36 C37 110.87(14) . . ?
C35 C36 C37 108.29(14) . . ?
C32 C37 C36 114.45(13) . . ?
C32 C37 H37A 108.6 . . ?
C36 C37 H37A 108.6 . . ?
C32 C37 H37B 108.6 . . ?
C36 C37 H37B 108.6 . . ?
H37A C37 H37B 107.6 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C34 C40 C41 121.92(16) . . ?
C34 C40 C42 120.99(17) . . ?
C41 C40 C42 117.01(16) . . ?
N3 C41 C40 178.76(19) . . ?
N4 C42 C40 178.7(2) . . ?
C45 C43 C24 112.06(14) . . ?
C45 C43 C44 108.09(15) . . ?
C24 C43 C44 111.40(14) . . ?
C45 C43 C46 109.27(17) . . ?
C24 C43 C46 108.23(13) . . ?
C44 C43 C46 107.69(15) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 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
C6 C1 C2 C3 -0.2(2) . . . . ?
C20 C1 C2 C3 177.85(15) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C5 1.6(2) . . . . ?
C2 C3 C4 C7 -178.53(15) . . . . ?
C3 C4 C5 C6 -1.5(2) . . . . ?
C7 C4 C5 C6 178.63(14) . . . . ?
C4 C5 C6 C1 0.6(2) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
C20 C1 C6 C5 -177.67(15) . . . . ?
C5 C4 C7 C8 -174.04(15) . . . . ?
C3 C4 C7 C8 6.1(2) . . . . ?
C4 C7 C8 C9 -178.79(15) . . . . ?
C7 C8 C9 C10 -177.16(15) . . . . ?
C7 C8 C9 C14 2.2(2) . . . . ?
C8 C9 C10 C11 -178.05(14) . . . . ?
C14 C9 C10 C11 2.6(2) . . . . ?
C9 C10 C11 C17 -177.40(15) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C17 C11 C12 C13 -158.01(14) . . . . ?
C10 C11 C12 C13 25.2(2) . . . . ?
C11 C12 C13 C16 -167.60(14) . . . . ?
C11 C12 C13 C15 72.19(17) . . . . ?
C11 C12 C13 C14 -48.82(18) . . . . ?
C10 C9 C14 C13 -29.1(2) . . . . ?
C8 C9 C14 C13 151.59(14) . . . . ?
C16 C13 C14 C9 169.01(13) . . . . ?
C15 C13 C14 C9 -70.48(17) . . . . ?
C12 C13 C14 C9 50.64(18) . . . . ?
C10 C11 C17 C18 5.3(2) . . . . ?
C12 C11 C17 C18 -171.48(15) . . . . ?
C10 C11 C17 C19 179.65(15) . . . . ?
C12 C11 C17 C19 2.9(2) . . . . ?
C11 C17 C18 N1 29(6) . . . . ?
C19 C17 C18 N1 -146(5) . . . . ?
C11 C17 C19 N2 -97(16) . . . . ?
C18 C17 C19 N2 78(16) . . . . ?
C6 C1 C20 C21 -14.1(2) . . . . ?
C2 C1 C20 C21 167.96(17) . . . . ?
C6 C1 C20 C23 105.7(2) . . . . ?
C2 C1 C20 C23 -72.2(2) . . . . ?
C6 C1 C20 C22 -133.74(18) . . . . ?
C2 C1 C20 C22 48.3(2) . . . . ?
C29 C24 C25 C26 0.7(3) . . . . ?
C43 C24 C25 C26 -176.05(16) . . . . ?
C24 C25 C26 C27 -0.1(3) . . . . ?
C25 C26 C27 C28 -0.1(3) . . . . ?
C25 C26 C27 C30 179.37(16) . . . . ?
C26 C27 C28 C29 -0.2(3) . . . . ?
C30 C27 C28 C29 -179.76(16) . . . . ?
C27 C28 C29 C24 0.8(3) . . . . ?
C25 C24 C29 C28 -1.0(3) . . . . ?
C43 C24 C29 C28 175.79(16) . . . . ?
C28 C27 C30 C31 -166.96(18) . . . . ?
C26 C27 C30 C31 13.5(3) . . . . ?
C27 C30 C31 C32 -177.38(16) . . . . ?
C30 C31 C32 C33 175.32(17) . . . . ?
C30 C31 C32 C37 -3.3(3) . . . . ?
C31 C32 C33 C34 -175.12(15) . . . . ?
C37 C32 C33 C34 3.5(3) . . . . ?
C32 C33 C34 C40 -177.20(17) . . . . ?
C32 C33 C34 C35 5.8(3) . . . . ?
C40 C34 C35 C36 146.43(17) . . . . ?
C33 C34 C35 C36 -36.6(2) . . . . ?
C34 C35 C36 C38 174.46(14) . . . . ?
C34 C35 C36 C39 -65.60(18) . . . . ?
C34 C35 C36 C37 55.65(18) . . . . ?
C33 C32 C37 C36 18.8(2) . . . . ?
C31 C32 C37 C36 -162.62(15) . . . . ?
C38 C36 C37 C32 -166.32(15) . . . . ?
C39 C36 C37 C32 73.51(19) . . . . ?
C35 C36 C37 C32 -47.12(19) . . . . ?
C33 C34 C40 C41 0.5(3) . . . . ?
C35 C34 C40 C41 177.41(17) . . . . ?
C33 C34 C40 C42 -176.17(17) . . . . ?
C35 C34 C40 C42 0.7(3) . . . . ?
C34 C40 C41 N3 23(12) . . . . ?
C42 C40 C41 N3 -160(12) . . . . ?
C34 C40 C42 N4 45(10) . . . . ?
C41 C40 C42 N4 -132(10) . . . . ?
C29 C24 C43 C45 161.48(17) . . . . ?
C25 C24 C43 C45 -21.9(2) . . . . ?
C29 C24 C43 C44 40.2(2) . . . . ?
C25 C24 C43 C44 -143.16(17) . . . . ?
C29 C24 C43 C46 -78.0(2) . . . . ?
C25 C24 C43 C46 98.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 994855'
#######################################################################
#
#                 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_bo3044

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 N2'
_chemical_formula_weight         350.45

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   5.9789(15)
_cell_length_b                   7.3765(18)
_cell_length_c                   43.952(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.422(4)
_cell_angle_gamma                90.00
_cell_volume                     1937.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    6343
_cell_measurement_theta_min      2.761
_cell_measurement_theta_max      29.110

_exptl_crystal_description       Chip
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  AFC10/Saturn724+
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22095
_diffrn_reflns_av_R_equivalents  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         2.78
_diffrn_reflns_theta_max         28.00
_reflns_number_total             4667
_reflns_number_gt                4117
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0651P)²+3.8600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4667
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2094
_refine_ls_wR_factor_gt          0.2023
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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
N1 N -0.5392(5) 0.0999(4) 0.11084(6) 0.0491(7) Uani 1 1 d . . .
N2 N -0.6022(4) 0.2756(4) 0.01715(6) 0.0452(7) Uani 1 1 d . . .
C1 C 1.0236(4) 0.6847(3) 0.27115(5) 0.0256(5) Uani 1 1 d . . .
H1 H 1.1025 0.7357 0.2547 0.031 Uiso 1 1 calc R . .
C2 C 1.1214(4) 0.6869(3) 0.30024(6) 0.0291(5) Uani 1 1 d . . .
H2 H 1.2649 0.7396 0.3035 0.035 Uiso 1 1 calc R . .
C3 C 1.0092(4) 0.6120(3) 0.32454(6) 0.0293(5) Uani 1 1 d . . .
H3 H 1.0758 0.6128 0.3444 0.035 Uiso 1 1 calc R . .
C4 C 0.7989(5) 0.5359(4) 0.31960(6) 0.0305(5) Uani 1 1 d . . .
H4 H 0.7209 0.4853 0.3362 0.037 Uiso 1 1 calc R . .
C5 C 0.7022(4) 0.5336(3) 0.29058(5) 0.0271(5) Uani 1 1 d . . .
H5 H 0.5590 0.4799 0.2875 0.033 Uiso 1 1 calc R . .
C6 C 0.8119(4) 0.6090(3) 0.26557(5) 0.0211(5) Uani 1 1 d . . .
C7 C 0.7062(4) 0.6085(3) 0.23446(5) 0.0215(5) Uani 1 1 d . . .
C8 C 0.4978(4) 0.5236(3) 0.22892(5) 0.0255(5) Uani 1 1 d . . .
H8 H 0.4261 0.4646 0.2452 0.031 Uiso 1 1 calc R . .
C9 C 0.3950(4) 0.5240(3) 0.20043(6) 0.0262(5) Uani 1 1 d . . .
H9 H 0.2545 0.4654 0.1976 0.031 Uiso 1 1 calc R . .
C10 C 0.4948(4) 0.6096(3) 0.17558(5) 0.0237(5) Uani 1 1 d . . .
C11 C 0.7029(4) 0.6931(3) 0.18099(5) 0.0268(5) Uani 1 1 d . . .
H11 H 0.7751 0.7514 0.1647 0.032 Uiso 1 1 calc R . .
C12 C 0.8052(4) 0.6922(3) 0.20962(5) 0.0259(5) Uani 1 1 d . . .
H12 H 0.9462 0.7501 0.2125 0.031 Uiso 1 1 calc R . .
C13 C 0.3885(4) 0.6182(3) 0.14534(5) 0.0262(5) Uani 1 1 d . . .
H13 H 0.4588 0.6902 0.1304 0.031 Uiso 1 1 calc R . .
C14 C 0.1981(4) 0.5316(4) 0.13706(6) 0.0295(5) Uani 1 1 d . . .
H14 H 0.1289 0.4600 0.1521 0.035 Uiso 1 1 calc R . .
C15 C 0.0890(4) 0.5379(3) 0.10720(5) 0.0271(5) Uani 1 1 d . . .
C16 C -0.0925(4) 0.4306(4) 0.10184(6) 0.0302(5) Uani 1 1 d . . .
H16 H -0.1476 0.3605 0.1182 0.036 Uiso 1 1 calc R . .
C17 C -0.2041(4) 0.4186(3) 0.07279(6) 0.0267(5) Uani 1 1 d . . .
C18 C -0.1103(4) 0.5250(4) 0.04691(5) 0.0289(5) Uani 1 1 d . . .
H18A H -0.2327 0.5536 0.0321 0.035 Uiso 1 1 calc R . .
H18B H 0.0004 0.4492 0.0364 0.035 Uiso 1 1 calc R . .
C19 C 0.0028(4) 0.7026(4) 0.05726(6) 0.0290(5) Uani 1 1 d . . .
C20 C 0.1762(4) 0.6602(4) 0.08262(5) 0.0279(5) Uani 1 1 d . . .
H20A H 0.3077 0.6019 0.0735 0.034 Uiso 1 1 calc R . .
H20B H 0.2271 0.7755 0.0920 0.034 Uiso 1 1 calc R . .
C21 C -0.1725(5) 0.8350(4) 0.06878(7) 0.0407(7) Uani 1 1 d . . .
H21A H -0.2833 0.8596 0.0525 0.049 Uiso 1 1 calc R . .
H21B H -0.0994 0.9485 0.0750 0.049 Uiso 1 1 calc R . .
H21C H -0.2472 0.7818 0.0863 0.049 Uiso 1 1 calc R . .
C22 C 0.1225(5) 0.7848(5) 0.03032(6) 0.0420(7) Uani 1 1 d . . .
H22A H 0.0125 0.8158 0.0143 0.050 Uiso 1 1 calc R . .
H22B H 0.2295 0.6968 0.0225 0.050 Uiso 1 1 calc R . .
H22C H 0.2023 0.8945 0.0369 0.050 Uiso 1 1 calc R . .
C23 C -0.3867(4) 0.3059(4) 0.06849(6) 0.0280(5) Uani 1 1 d . . .
C24 C -0.4712(4) 0.1949(4) 0.09225(6) 0.0328(6) Uani 1 1 d . . .
C25 C -0.5032(4) 0.2904(4) 0.03967(6) 0.0326(6) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C24 1.158(4) . ?
N2 C25 1.146(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.400(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.492(3) . ?
C7 C12 1.399(3) . ?
C7 C8 1.410(3) . ?
C8 C9 1.381(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(3) . ?
C10 C13 1.460(3) . ?
C11 C12 1.386(3) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.348(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.452(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.359(3) . ?
C15 C20 1.510(3) . ?
C16 C17 1.429(3) . ?
C16 H16 0.9500 . ?
C17 C23 1.381(3) . ?
C17 C18 1.502(3) . ?
C18 C19 1.538(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C22 1.524(4) . ?
C19 C21 1.528(4) . ?
C19 C20 1.536(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.429(4) . ?
C23 C25 1.435(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
C2 C1 C6 121.5(2) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.4(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 117.2(2) . . ?
C1 C6 C7 121.5(2) . . ?
C5 C6 C7 121.3(2) . . ?
C12 C7 C8 116.8(2) . . ?
C12 C7 C6 122.4(2) . . ?
C8 C7 C6 120.8(2) . . ?
C9 C8 C7 121.8(2) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 C13 119.9(2) . . ?
C9 C10 C13 122.9(2) . . ?
C12 C11 C10 121.5(2) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C7 121.7(2) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C14 C13 C10 124.8(2) . . ?
C14 C13 H13 117.6 . . ?
C10 C13 H13 117.6 . . ?
C13 C14 C15 125.9(2) . . ?
C13 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C16 C15 C14 118.5(2) . . ?
C16 C15 C20 120.8(2) . . ?
C14 C15 C20 120.7(2) . . ?
C15 C16 C17 123.0(2) . . ?
C15 C16 H16 118.5 . . ?
C17 C16 H16 118.5 . . ?
C23 C17 C16 120.7(2) . . ?
C23 C17 C18 121.3(2) . . ?
C16 C17 C18 118.0(2) . . ?
C17 C18 C19 113.0(2) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C22 C19 C21 110.0(2) . . ?
C22 C19 C20 108.9(2) . . ?
C21 C19 C20 110.2(2) . . ?
C22 C19 C18 108.7(2) . . ?
C21 C19 C18 110.0(2) . . ?
C20 C19 C18 109.0(2) . . ?
C15 C20 C19 113.7(2) . . ?
C15 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C15 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 C24 122.5(2) . . ?
C17 C23 C25 122.3(2) . . ?
C24 C23 C25 115.3(2) . . ?
N1 C24 C23 177.7(3) . . ?
N2 C25 C23 177.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C2 C1 C6 C5 -0.5(3) . . . . ?
C2 C1 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -179.2(2) . . . . ?
C1 C6 C7 C12 -3.9(3) . . . . ?
C5 C6 C7 C12 175.9(2) . . . . ?
C1 C6 C7 C8 176.8(2) . . . . ?
C5 C6 C7 C8 -3.4(3) . . . . ?
C12 C7 C8 C9 -0.4(4) . . . . ?
C6 C7 C8 C9 178.9(2) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C13 -177.9(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C13 C10 C11 C12 178.0(2) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C8 C7 C12 C11 0.4(4) . . . . ?
C6 C7 C12 C11 -178.9(2) . . . . ?
C11 C10 C13 C14 174.7(2) . . . . ?
C9 C10 C13 C14 -7.0(4) . . . . ?
C10 C13 C14 C15 -180.0(2) . . . . ?
C13 C14 C15 C16 174.6(3) . . . . ?
C13 C14 C15 C20 -5.1(4) . . . . ?
C14 C15 C16 C17 -176.3(2) . . . . ?
C20 C15 C16 C17 3.4(4) . . . . ?
C15 C16 C17 C23 179.3(2) . . . . ?
C15 C16 C17 C18 2.2(4) . . . . ?
C23 C17 C18 C19 151.3(2) . . . . ?
C16 C17 C18 C19 -31.5(3) . . . . ?
C17 C18 C19 C22 171.4(2) . . . . ?
C17 C18 C19 C21 -68.1(3) . . . . ?
C17 C18 C19 C20 52.9(3) . . . . ?
C16 C15 C20 C19 20.8(3) . . . . ?
C14 C15 C20 C19 -159.5(2) . . . . ?
C22 C19 C20 C15 -165.9(2) . . . . ?
C21 C19 C20 C15 73.3(3) . . . . ?
C18 C19 C20 C15 -47.5(3) . . . . ?
C16 C17 C23 C24 -0.9(4) . . . . ?
C18 C17 C23 C24 176.2(2) . . . . ?
C16 C17 C23 C25 179.9(2) . . . . ?
C18 C17 C23 C25 -3.0(4) . . . . ?
C17 C23 C24 N1 -127(8) . . . . ?
C25 C23 C24 N1 52(8) . . . . ?
C17 C23 C25 N2 -161(8) . . . . ?
C24 C23 C25 N2 20(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.068
_database_code_depnum_ccdc_archive 'CCDC 1003775'
