# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_b
_database_code_depnum_ccdc_archive 'CCDC 1013665'
_audit_update_record             
;
2014-07-14 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Br2 N2'
_chemical_formula_sum            'C22 H24 Br2 N2'
_chemical_formula_weight         476.25

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'
Br Br -0.6763 1.2805 '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                   9.1241(2)
_cell_length_b                   10.2171(2)
_cell_length_c                   11.3635(8)
_cell_angle_alpha                78.194(6)
_cell_angle_beta                 82.379(6)
_cell_angle_gamma                72.418(5)
_cell_volume                     985.63(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    12173
_cell_measurement_theta_min      6.6
_cell_measurement_theta_max      68.2

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    5.264
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.639
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12869
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0398
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.61
_diffrn_reflns_theta_max         68.24
_reflns_number_total             3484
_reflns_number_gt                3023
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'CrystalClear-SM Auto 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_molecular_graphics    'CrystalStructure 4.0'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0612P)²+1.0667P] 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         3484
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1361
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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
Br1 Br 0.28391(7) 0.48347(7) 1.04692(5) 0.0793(2) Uani 1 1 d . . .
Br2 Br 0.43811(5) 0.22456(5) 0.36831(4) 0.05883(19) Uani 1 1 d . . .
N1 N 0.1753(4) 0.0413(3) 0.8106(3) 0.0513(8) Uani 1 1 d . . .
C16 C -0.2788(7) 0.0741(5) 0.6516(5) 0.0740(14) Uani 1 1 d . . .
H16A H -0.3705 0.1200 0.6099 0.111 Uiso 1 1 calc R . .
H16B H -0.2959 -0.0020 0.7115 0.111 Uiso 1 1 calc R . .
H16C H -0.1951 0.0393 0.5951 0.111 Uiso 1 1 calc R . .
C1 C -0.4659(6) 0.3746(6) 0.6767(5) 0.0725(14) Uani 1 1 d . . .
H1A H -0.5438 0.3461 0.6462 0.087 Uiso 1 1 calc R . .
H1B H -0.5148 0.4612 0.7064 0.087 Uiso 1 1 calc R . .
C2 C -0.3851(5) 0.2611(6) 0.7771(4) 0.0632(12) Uani 1 1 d . . .
H2A H -0.3597 0.3022 0.8386 0.076 Uiso 1 1 calc R . .
H2B H -0.4500 0.2019 0.8143 0.076 Uiso 1 1 calc R . .
C3 C -0.2388(5) 0.1781(4) 0.7128(3) 0.0463(9) Uani 1 1 d . . .
C4 C -0.1060(5) 0.1110(4) 0.7933(3) 0.0483(9) Uani 1 1 d . . .
H4A H -0.1267 0.0307 0.8470 0.058 Uiso 1 1 calc R . .
H4B H -0.1030 0.1770 0.8427 0.058 Uiso 1 1 calc R . .
C5 C 0.0533(5) 0.0639(4) 0.7270(3) 0.0448(8) Uani 1 1 d . . .
C6 C 0.1969(4) 0.1430(4) 0.8628(3) 0.0426(8) Uani 1 1 d . . .
C7 C 0.1285(5) 0.2867(4) 0.8246(4) 0.0482(9) Uani 1 1 d . . .
H7 H 0.0650 0.3151 0.7611 0.058 Uiso 1 1 calc R . .
C8 C 0.1534(5) 0.3857(5) 0.8789(4) 0.0545(10) Uani 1 1 d . . .
H8 H 0.1070 0.4798 0.8518 0.065 Uiso 1 1 calc R . .
C9 C 0.2472(5) 0.3459(5) 0.9735(4) 0.0517(9) Uani 1 1 d . . .
C10 C 0.0722(4) 0.1662(4) 0.6119(3) 0.0397(8) Uani 1 1 d . . .
C11 C 0.2166(5) 0.1573(4) 0.5536(3) 0.0445(8) Uani 1 1 d . . .
H11 H 0.3020 0.0910 0.5870 0.053 Uiso 1 1 calc R . .
C12 C 0.2365(4) 0.2449(4) 0.4468(3) 0.0431(8) Uani 1 1 d . . .
C13 C 0.1114(5) 0.3449(4) 0.3963(3) 0.0476(9) Uani 1 1 d . . .
H13 H 0.1253 0.4033 0.3240 0.057 Uiso 1 1 calc R . .
C14 C -0.0327(5) 0.3577(4) 0.4527(4) 0.0473(9) Uani 1 1 d . . .
H14 H -0.1164 0.4255 0.4182 0.057 Uiso 1 1 calc R . .
C15 C -0.0569(5) 0.2705(4) 0.5619(3) 0.0428(8) Uani 1 1 d . . .
N2 N -0.2000(4) 0.2889(4) 0.6232(3) 0.0556(9) Uani 1 1 d . . .
C17 C -0.3376(5) 0.3924(5) 0.5771(5) 0.0598(11) Uani 1 1 d . . .
H17A H -0.3595 0.3747 0.5016 0.072 Uiso 1 1 calc R . .
H17B H -0.3260 0.4857 0.5647 0.072 Uiso 1 1 calc R . .
C18 C 0.0913(7) -0.0858(4) 0.6973(4) 0.0661(13) Uani 1 1 d . . .
H18A H -0.0005 -0.1031 0.6772 0.079 Uiso 1 1 calc R . .
H18B H 0.1687 -0.0981 0.6301 0.079 Uiso 1 1 calc R . .
C19 C 0.1512(8) -0.1822(5) 0.8108(5) 0.0796(16) Uani 1 1 d . . .
H19A H 0.0668 -0.2010 0.8665 0.096 Uiso 1 1 calc R . .
H19B H 0.2198 -0.2698 0.7923 0.096 Uiso 1 1 calc R . .
C20 C 0.2350(6) -0.1072(4) 0.8625(4) 0.0646(13) Uani 1 1 d . . .
H20A H 0.3449 -0.1403 0.8418 0.078 Uiso 1 1 calc R . .
H20B H 0.2169 -0.1213 0.9496 0.078 Uiso 1 1 calc R . .
C21 C 0.2928(5) 0.1070(5) 0.9586(3) 0.0515(10) Uani 1 1 d . . .
H21 H 0.3416 0.0135 0.9859 0.062 Uiso 1 1 calc R . .
C22 C 0.3159(5) 0.2081(5) 1.0130(4) 0.0568(11) Uani 1 1 d . . .
H22 H 0.3787 0.1818 1.0769 0.068 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.903(4) . ?
Br2 C12 1.906(4) . ?
N1 C6 1.370(5) . ?
N1 C20 1.472(5) . ?
N1 C5 1.493(5) . ?
C16 C3 1.533(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C1 C17 1.542(7) . ?
C1 C2 1.534(7) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.532(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 N2 1.455(5) . ?
C3 C4 1.520(6) . ?
C4 C5 1.532(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C10 1.524(5) . ?
C5 C18 1.560(5) . ?
C6 C21 1.407(5) . ?
C6 C7 1.411(5) . ?
C7 C8 1.374(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(6) . ?
C8 H8 0.9300 . ?
C9 C22 1.364(7) . ?
C10 C11 1.379(6) . ?
C10 C15 1.420(5) . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.381(6) . ?
C13 C14 1.365(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.407(5) . ?
C14 H14 0.9300 . ?
C15 N2 1.374(5) . ?
N2 C17 1.454(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.508(7) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.474(8) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.386(7) . ?
C21 H21 0.9300 . ?
C22 H22 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
C6 N1 C20 121.0(3) . . ?
C6 N1 C5 124.7(3) . . ?
C20 N1 C5 111.4(4) . . ?
C3 C16 H16A 109.5 . . ?
C3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C17 C1 C2 105.5(4) . . ?
C17 C1 H1A 110.6 . . ?
C2 C1 H1A 110.6 . . ?
C17 C1 H1B 110.6 . . ?
C2 C1 H1B 110.6 . . ?
H1A C1 H1B 108.8 . . ?
C3 C2 C1 104.4(4) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N2 C3 C4 108.5(3) . . ?
N2 C3 C16 110.6(4) . . ?
C4 C3 C16 113.3(4) . . ?
N2 C3 C2 100.7(3) . . ?
C4 C3 C2 113.6(3) . . ?
C16 C3 C2 109.4(4) . . ?
C3 C4 C5 115.3(3) . . ?
C3 C4 H4A 108.4 . . ?
C5 C4 H4A 108.4 . . ?
C3 C4 H4B 108.4 . . ?
C5 C4 H4B 108.4 . . ?
H4A C4 H4B 107.5 . . ?
N1 C5 C10 112.2(3) . . ?
N1 C5 C4 109.5(3) . . ?
C10 C5 C4 111.8(3) . . ?
N1 C5 C18 100.1(3) . . ?
C10 C5 C18 109.6(3) . . ?
C4 C5 C18 113.2(4) . . ?
N1 C6 C21 120.3(3) . . ?
N1 C6 C7 123.3(3) . . ?
C21 C6 C7 116.4(4) . . ?
C8 C7 C6 121.7(4) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 120.1(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C22 C9 C8 120.1(4) . . ?
C22 C9 Br1 119.9(3) . . ?
C8 C9 Br1 120.1(3) . . ?
C11 C10 C15 118.9(3) . . ?
C11 C10 C5 119.9(3) . . ?
C15 C10 C5 121.2(3) . . ?
C12 C11 C10 121.2(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 Br2 119.4(3) . . ?
C13 C12 Br2 120.3(3) . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C15 121.2(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
N2 C15 C14 121.5(3) . . ?
N2 C15 C10 120.0(3) . . ?
C14 C15 C10 118.4(4) . . ?
C15 N2 C17 123.0(3) . . ?
C15 N2 C3 121.8(3) . . ?
C17 N2 C3 111.4(3) . . ?
N2 C17 C1 103.9(4) . . ?
N2 C17 H17A 111.0 . . ?
C1 C17 H17A 111.0 . . ?
N2 C17 H17B 111.0 . . ?
C1 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C19 C18 C5 104.9(4) . . ?
C19 C18 H18A 110.8 . . ?
C5 C18 H18A 110.8 . . ?
C19 C18 H18B 110.8 . . ?
C5 C18 H18B 110.8 . . ?
H18A C18 H18B 108.8 . . ?
C20 C19 C18 105.0(4) . . ?
C20 C19 H19A 110.7 . . ?
C18 C19 H19A 110.7 . . ?
C20 C19 H19B 110.7 . . ?
C18 C19 H19B 110.7 . . ?
H19A C19 H19B 108.8 . . ?
C19 C20 N1 106.4(4) . . ?
C19 C20 H20A 110.5 . . ?
N1 C20 H20A 110.5 . . ?
C19 C20 H20B 110.5 . . ?
N1 C20 H20B 110.5 . . ?
H20A C20 H20B 108.6 . . ?
C22 C21 C6 121.3(4) . . ?
C22 C21 H21 119.4 . . ?
C6 C21 H21 119.4 . . ?
C9 C22 C21 120.4(4) . . ?
C9 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        68.24
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.463
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.159
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1013666'
_audit_update_record             
;
2014-07-14 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N2'
_chemical_formula_sum            'C20 H22 N2'
_chemical_formula_weight         290.39

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.49870(10)
_cell_length_b                   7.90730(10)
_cell_length_c                   14.5997(10)
_cell_angle_alpha                77.721(6)
_cell_angle_beta                 79.566(6)
_cell_angle_gamma                69.529(5)
_cell_volume                     787.06(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9997
_cell_measurement_theta_min      6.70
_cell_measurement_theta_max      68.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.548
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.829
_exptl_absorpt_correction_T_max  0.951
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11432
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.738
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             2784
_reflns_number_gt                2268
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0851P)²+0.1193P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2784
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1397
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_restrained_S_all      1.217
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2603(2) -0.0512(2) 0.16128(10) 0.0501(4) Uani 1 1 d . . . . .
N2 N -0.0511(2) 0.1812(2) 0.39161(10) 0.0518(4) Uani 1 1 d . . . . .
C1 C -0.3427(3) 0.1753(4) 0.48221(16) 0.0793(7) Uani 1 1 d . . . . .
H1A H -0.3341 0.0923 0.5418 0.095 Uiso 1 1 calc R U . . .
H1B H -0.4695 0.2660 0.4834 0.095 Uiso 1 1 calc R U . . .
C2 C -0.3047(3) 0.0710(3) 0.40057(15) 0.0669(6) Uani 1 1 d . . . . .
H2A H -0.4219 0.0956 0.3735 0.080 Uiso 1 1 calc R U . . .
H2B H -0.2516 -0.0596 0.4214 0.080 Uiso 1 1 calc R U . . .
C3 C -0.1614(2) 0.1409(3) 0.32925(13) 0.0515(4) Uani 1 1 d . . . . .
H3 H -0.2320 0.2567 0.2926 0.062 Uiso 1 1 calc R U . . .
C4 C -0.0327(2) 0.0161(2) 0.26061(12) 0.0487(4) Uani 1 1 d . . . . .
H4 H -0.0427 -0.1066 0.2827 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1787(2) 0.0022(2) 0.25336(11) 0.0423(4) Uani 1 1 d . . . . .
H5 H 0.2393 -0.0975 0.3020 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4462(2) -0.1654(2) 0.14422(12) 0.0481(4) Uani 1 1 d . . . . .
C7 C 0.5796(3) -0.2099(3) 0.20853(14) 0.0558(5) Uani 1 1 d . . . . .
H7 H 0.5439 -0.1606 0.2641 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7637(3) -0.3262(3) 0.19028(17) 0.0660(6) Uani 1 1 d . . . . .
H8 H 0.8502 -0.3550 0.2340 0.079 Uiso 1 1 calc R U . . .
C9 C 0.8210(3) -0.4003(3) 0.10821(18) 0.0747(7) Uani 1 1 d . . . . .
H9 H 0.9452 -0.4787 0.0964 0.090 Uiso 1 1 calc R U . . .
C10 C 0.1112(3) -0.0316(3) 0.10400(13) 0.0558(5) Uani 1 1 d . . . . .
H10A H 0.1078 -0.1503 0.0980 0.067 Uiso 1 1 calc R U . . .
H10B H 0.1322 0.0356 0.0415 0.067 Uiso 1 1 calc R U . . .
C11 C -0.0717(3) 0.0734(3) 0.15776(13) 0.0567(5) Uani 1 1 d . . . . .
H11A H -0.1793 0.0409 0.1480 0.068 Uiso 1 1 calc R U . . .
H11B H -0.0986 0.2042 0.1383 0.068 Uiso 1 1 calc R U . . .
C12 C 0.2040(2) 0.1759(2) 0.26767(11) 0.0419(4) Uani 1 1 d . . . . .
C13 C 0.0898(2) 0.2568(2) 0.34431(11) 0.0458(4) Uani 1 1 d . . . . .
C14 C -0.1892(3) 0.2674(3) 0.46540(14) 0.0675(6) Uani 1 1 d . . . . .
H14A H -0.2432 0.3981 0.4450 0.081 Uiso 1 1 calc R U . . .
H14B H -0.1298 0.2468 0.5223 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1234(3) 0.4035(3) 0.36866(14) 0.0592(5) Uani 1 1 d . . . . .
H15 H 0.0531 0.4545 0.4212 0.071 Uiso 1 1 calc R U . . .
C16 C 0.2610(3) 0.4730(3) 0.31481(16) 0.0632(5) Uani 1 1 d . . . . .
H16 H 0.2831 0.5702 0.3318 0.076 Uiso 1 1 calc R U . . .
C17 C 0.3656(3) 0.4010(3) 0.23669(15) 0.0601(5) Uani 1 1 d . . . . .
H17 H 0.4542 0.4521 0.1994 0.072 Uiso 1 1 calc R U . . .
C18 C 0.3378(2) 0.2507(2) 0.21378(12) 0.0492(4) Uani 1 1 d . . . . .
H18 H 0.4101 0.2001 0.1615 0.059 Uiso 1 1 calc R U . . .
C19 C 0.5078(3) -0.2407(3) 0.06085(13) 0.0614(5) Uani 1 1 d . . . . .
H19 H 0.4234 -0.2122 0.0161 0.074 Uiso 1 1 calc R U . . .
C20 C 0.6924(3) -0.3567(3) 0.04447(16) 0.0751(6) Uani 1 1 d . . . . .
H20 H 0.7303 -0.4062 -0.0110 0.090 Uiso 1 1 calc R U . . .


_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 C6 1.382(2) . ?
N1 C5 1.457(2) . ?
N1 C10 1.461(2) . ?
N2 C13 1.397(2) . ?
N2 C14 1.453(2) . ?
N2 C3 1.482(2) . ?
C1 C2 1.521(3) . ?
C1 C14 1.525(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.520(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.521(2) . ?
C3 H3 0.9800 . ?
C4 C11 1.524(2) . ?
C4 C5 1.535(2) . ?
C4 H4 0.9800 . ?
C5 C12 1.512(2) . ?
C5 H5 0.9800 . ?
C6 C7 1.400(3) . ?
C6 C19 1.401(2) . ?
C7 C8 1.380(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C20 1.368(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C18 1.381(2) . ?
C12 C13 1.403(2) . ?
C13 C15 1.396(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 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
C6 N1 C5 122.55(14) . . ?
C6 N1 C10 122.00(14) . . ?
C5 N1 C10 111.58(13) . . ?
C13 N2 C14 120.25(15) . . ?
C13 N2 C3 114.72(13) . . ?
C14 N2 C3 106.71(15) . . ?
C2 C1 C14 106.08(16) . . ?
C2 C1 H1A 110.5 . . ?
C14 C1 H1A 110.5 . . ?
C2 C1 H1B 110.5 . . ?
C14 C1 H1B 110.5 . . ?
H1A C1 H1B 108.7 . . ?
C1 C2 C3 104.89(17) . . ?
C1 C2 H2A 110.8 . . ?
C3 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C3 C2 H2B 110.8 . . ?
H2A C2 H2B 108.8 . . ?
N2 C3 C2 101.63(15) . . ?
N2 C3 C4 112.32(14) . . ?
C2 C3 C4 117.70(16) . . ?
N2 C3 H3 108.2 . . ?
C2 C3 H3 108.2 . . ?
C4 C3 H3 108.2 . . ?
C3 C4 C11 116.60(16) . . ?
C3 C4 C5 112.66(14) . . ?
C11 C4 C5 102.14(13) . . ?
C3 C4 H4 108.4 . . ?
C11 C4 H4 108.4 . . ?
C5 C4 H4 108.4 . . ?
N1 C5 C12 114.49(13) . . ?
N1 C5 C4 104.09(13) . . ?
C12 C5 C4 112.88(13) . . ?
N1 C5 H5 108.4 . . ?
C12 C5 H5 108.4 . . ?
C4 C5 H5 108.4 . . ?
N1 C6 C7 121.88(16) . . ?
N1 C6 C19 120.60(17) . . ?
C7 C6 C19 117.52(17) . . ?
C8 C7 C6 120.67(19) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C20 C9 C8 118.94(19) . . ?
C20 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
N1 C10 C11 104.00(14) . . ?
N1 C10 H10A 111.0 . . ?
C11 C10 H10A 111.0 . . ?
N1 C10 H10B 111.0 . . ?
C11 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
C10 C11 C4 104.14(15) . . ?
C10 C11 H11A 110.9 . . ?
C4 C11 H11A 110.9 . . ?
C10 C11 H11B 110.9 . . ?
C4 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
C18 C12 C13 119.52(15) . . ?
C18 C12 C5 124.02(15) . . ?
C13 C12 C5 116.36(14) . . ?
C15 C13 N2 124.57(16) . . ?
C15 C13 C12 119.12(16) . . ?
N2 C13 C12 116.32(14) . . ?
N2 C14 C1 104.29(17) . . ?
N2 C14 H14A 110.9 . . ?
C1 C14 H14A 110.9 . . ?
N2 C14 H14B 110.9 . . ?
C1 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C16 C15 C13 120.00(18) . . ?
C16 C15 H15 120.0 . . ?
C13 C15 H15 120.0 . . ?
C17 C16 C15 121.06(17) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 119.32(17) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C12 C18 C17 120.81(17) . . ?
C12 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C20 C19 C6 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C6 C19 H19 119.7 . . ?
C9 C20 C19 121.3(2) . . ?
C9 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.132

_shelxl_version_number           2013-2



