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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1019798'
_audit_update_record             
;
2014-08-18 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H12 Br N'
_chemical_formula_weight         310.19

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'
Br Br -0.2901 2.4595 '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'

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

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

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

_cell_length_a                   28.494(6)
_cell_length_b                   7.2296(14)
_cell_length_c                   6.2594(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.33(3)
_cell_angle_gamma                90
_cell_volume                     1288.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    13560
_cell_measurement_theta_min      6.5
_cell_measurement_theta_max      58.7

_exptl_crystal_description       platelet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.482
_exptl_crystal_size_mid          0.465
_exptl_crystal_size_min          0.241
_exptl_absorpt_coefficient_mu    3.174
_shelx_estimated_absorpt_T_min   0.310
_shelx_estimated_absorpt_T_max   0.515
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0907
_exptl_absorpt_correction_T_max  0.7225
_exptl_absorpt_process_details   'face indexed'

_exptl_special_details           
;
programs X-Red32 and X-Shape by STOE & Cie GmbH 2010
;

_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12856
_diffrn_reflns_av_unetI/netI     0.0568
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.543
_diffrn_reflns_theta_max         29.362
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.947
_reflns_number_total             3336
_reflns_number_gt                2663
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0355P)²+0.7298P] 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         3336
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0995
_refine_ls_wR_factor_gt          0.0913
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_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_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
C1 C 0.09672(8) 0.4881(3) 0.6489(4) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.08688(9) 0.5238(4) 0.4352(4) 0.0325(5) Uani 1 1 d . . . . .
H2 H 0.0556 0.5268 0.3766 0.039 Uiso 1 1 calc R U . . .
C3 C 0.12524(10) 0.5552(4) 0.3113(4) 0.0322(5) Uani 1 1 d . . . . .
H3 H 0.1209 0.5793 0.1626 0.039 Uiso 1 1 calc R U . . .
C4 C 0.16990(9) 0.5509(3) 0.4059(4) 0.0275(5) Uani 1 1 d . . . . .
H4 H 0.1965 0.5733 0.3230 0.033 Uiso 1 1 calc R U . . .
C5 C 0.17553(8) 0.5137(3) 0.6231(3) 0.0207(4) Uani 1 1 d . . . . .
C6 C 0.22264(8) 0.5083(3) 0.7322(3) 0.0194(4) Uani 1 1 d . . . . .
C7 C 0.26163(8) 0.5875(3) 0.6407(3) 0.0236(4) Uani 1 1 d . . . . .
H7 H 0.2580 0.6459 0.5050 0.028 Uiso 1 1 calc R U . . .
C8 C 0.30552(8) 0.5827(3) 0.7435(4) 0.0237(4) Uani 1 1 d . . . . .
H8 H 0.3314 0.6371 0.6760 0.028 Uiso 1 1 calc R U . . .
C9 C 0.31290(8) 0.4998(3) 0.9445(3) 0.0189(4) Uani 1 1 d . . . . .
C10 C 0.27364(8) 0.4192(3) 1.0341(3) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.2772 0.3601 1.1693 0.027 Uiso 1 1 calc R U . . .
C11 C 0.22950(8) 0.4231(3) 0.9306(3) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.2036 0.3669 0.9964 0.026 Uiso 1 1 calc R U . . .
C12 C 0.35999(8) 0.4994(3) 1.0545(3) 0.0193(4) Uani 1 1 d . . . . .
C13 C 0.39853(8) 0.5831(3) 0.9624(4) 0.0260(5) Uani 1 1 d . . . . .
H13 H 0.3943 0.6435 0.8282 0.031 Uiso 1 1 calc R U . . .
C14 C 0.44282(9) 0.5797(3) 1.0627(4) 0.0287(5) Uani 1 1 d . . . . .
H14 H 0.4684 0.6378 0.9969 0.034 Uiso 1 1 calc R U . . .
C15 C 0.45000(9) 0.4922(3) 1.2582(4) 0.0286(5) Uani 1 1 d . . . . .
H15 H 0.4805 0.4873 1.3253 0.034 Uiso 1 1 calc R U . . .
C16 C 0.41234(10) 0.4123(3) 1.3539(4) 0.0292(5) Uani 1 1 d . . . . .
H16 H 0.4168 0.3538 1.4892 0.035 Uiso 1 1 calc R U . . .
C17 C 0.36778(9) 0.4165(3) 1.2544(4) 0.0261(5) Uani 1 1 d . . . . .
H17 H 0.3422 0.3619 1.3237 0.031 Uiso 1 1 calc R U . . .
Br1 Br 0.04511(2) 0.44356(4) 0.82642(4) 0.03840(10) Uani 1 1 d . . . . .
N1 N 0.13858(7) 0.4815(3) 0.7446(3) 0.0238(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
C1 N1 1.314(3) . ?
C1 C2 1.380(4) . ?
C1 Br1 1.906(2) . ?
C2 C3 1.385(4) . ?
C3 C4 1.382(3) . ?
C4 C5 1.389(3) . ?
C5 N1 1.344(3) . ?
C5 C6 1.482(3) . ?
C6 C11 1.393(3) . ?
C6 C7 1.393(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.398(3) . ?
C9 C12 1.483(3) . ?
C10 C11 1.391(3) . ?
C12 C17 1.397(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.387(3) . ?
C14 C15 1.385(4) . ?
C15 C16 1.377(4) . ?
C16 C17 1.392(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
N1 C1 C2 126.4(2) . . ?
N1 C1 Br1 115.82(17) . . ?
C2 C1 Br1 117.74(19) . . ?
C1 C2 C3 116.1(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 119.4(2) . . ?
N1 C5 C4 121.7(2) . . ?
N1 C5 C6 116.79(19) . . ?
C4 C5 C6 121.5(2) . . ?
C11 C6 C7 117.6(2) . . ?
C11 C6 C5 120.94(19) . . ?
C7 C6 C5 121.49(19) . . ?
C8 C7 C6 121.28(19) . . ?
C7 C8 C9 121.9(2) . . ?
C10 C9 C8 116.4(2) . . ?
C10 C9 C12 122.44(19) . . ?
C8 C9 C12 121.16(19) . . ?
C11 C10 C9 121.84(19) . . ?
C10 C11 C6 121.0(2) . . ?
C17 C12 C13 117.1(2) . . ?
C17 C12 C9 121.6(2) . . ?
C13 C12 C9 121.23(19) . . ?
C14 C13 C12 121.4(2) . . ?
C15 C14 C13 120.5(2) . . ?
C16 C15 C14 119.1(2) . . ?
C15 C16 C17 120.6(2) . . ?
C16 C17 C12 121.3(2) . . ?
C1 N1 C5 116.96(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 0.2(4) . . . . ?
Br1 C1 C2 C3 -179.9(2) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?
C3 C4 C5 N1 0.0(3) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
N1 C5 C6 C11 18.0(3) . . . . ?
C4 C5 C6 C11 -162.2(2) . . . . ?
N1 C5 C6 C7 -162.1(2) . . . . ?
C4 C5 C6 C7 17.7(3) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 179.7(2) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C7 C8 C9 C12 -178.7(2) . . . . ?
C8 C9 C10 C11 -0.8(3) . . . . ?
C12 C9 C10 C11 178.9(2) . . . . ?
C9 C10 C11 C6 0.0(3) . . . . ?
C7 C6 C11 C10 0.6(3) . . . . ?
C5 C6 C11 C10 -179.5(2) . . . . ?
C10 C9 C12 C17 0.5(3) . . . . ?
C8 C9 C12 C17 -179.7(2) . . . . ?
C10 C9 C12 C13 -179.2(2) . . . . ?
C8 C9 C12 C13 0.6(3) . . . . ?
C17 C12 C13 C14 1.6(3) . . . . ?
C9 C12 C13 C14 -178.7(2) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 -1.5(4) . . . . ?
C14 C15 C16 C17 1.1(4) . . . . ?
C15 C16 C17 C12 0.7(4) . . . . ?
C13 C12 C17 C16 -2.0(3) . . . . ?
C9 C12 C17 C16 178.2(2) . . . . ?
C2 C1 N1 C5 0.4(4) . . . . ?
Br1 C1 N1 C5 -179.55(16) . . . . ?
C4 C5 N1 C1 -0.5(3) . . . . ?
C6 C5 N1 C1 179.32(19) . . . . ?

_refine_diff_density_max         0.424
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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 1019799'
_audit_update_record             
;
2014-08-18 deposited with the CCDC.
2015-06-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N'
_chemical_formula_weight         331.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.4697(13)
_cell_length_b                   11.008(2)
_cell_length_c                   25.007(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1781.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    14512
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      53.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.447
_exptl_crystal_size_mid          0.419
_exptl_crystal_size_min          0.389
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.973
_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      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'STOE IPDS2T'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14188
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.252
_diffrn_reflns_theta_max         26.756
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3767
_reflns_number_gt                2826
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_max     0.993
_reflns_Friedel_fraction_full    1.000

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0417P)²] 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_abs_structure_details 
;
 Flack x determined using 1043 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3767
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0861
_refine_ls_wR_factor_gt          0.0800
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_restrained_S_all      0.924
_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_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
C1 C 0.2985(3) 0.82433(19) 0.28967(10) 0.0319(5) Uani 1 1 d . . . . .
C2 C 0.2359(4) 0.8783(2) 0.33855(10) 0.0375(6) Uani 1 1 d . . . . .
H2 H 0.3012 0.8551 0.3710 0.045 Uiso 1 1 calc R U . . .
C3 C 0.0817(4) 0.9637(2) 0.33929(13) 0.0494(7) Uani 1 1 d . . . . .
H3 H 0.0430 1.0003 0.3722 0.059 Uiso 1 1 calc R U . . .
C4 C -0.0193(4) 0.9978(2) 0.29220(15) 0.0575(8) Uani 1 1 d . . . . .
H4 H -0.1299 1.0545 0.2936 0.069 Uiso 1 1 calc R U . . .
C5 C 0.0394(4) 0.9504(3) 0.24477(14) 0.0518(8) Uani 1 1 d . . . . .
H5 H -0.0297 0.9751 0.2130 0.062 Uiso 1 1 calc R U . . .
C6 C 0.2029(4) 0.8642(2) 0.24142(11) 0.0401(6) Uani 1 1 d . . . . .
C7 C 0.2715(4) 0.8187(3) 0.19224(11) 0.0460(7) Uani 1 1 d . . . . .
H7 H 0.2097 0.8468 0.1601 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4266(4) 0.7341(3) 0.18991(11) 0.0459(7) Uani 1 1 d . . . . .
H8 H 0.4723 0.7041 0.1563 0.055 Uiso 1 1 calc R U . . .
C9 C 0.5175(4) 0.6919(2) 0.23721(10) 0.0381(6) Uani 1 1 d . . . . .
H9 H 0.6234 0.6323 0.2352 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4580(3) 0.73438(19) 0.28628(9) 0.0301(5) Uani 1 1 d . . . . .
C11 C 0.5608(3) 0.6857(2) 0.33501(9) 0.0298(5) Uani 1 1 d . . . . .
C12 C 0.7751(4) 0.6827(2) 0.33906(10) 0.0327(5) Uani 1 1 d . . . . .
H12 H 0.8588 0.7123 0.3107 0.039 Uiso 1 1 calc R U . . .
C13 C 0.8648(4) 0.6360(2) 0.38479(10) 0.0368(6) Uani 1 1 d . . . . .
H13 H 1.0109 0.6322 0.3882 0.044 Uiso 1 1 calc R U . . .
C14 C 0.7385(4) 0.5949(2) 0.42556(10) 0.0365(6) Uani 1 1 d . . . . .
H14 H 0.7966 0.5633 0.4576 0.044 Uiso 1 1 calc R U . . .
C15 C 0.5264(4) 0.60052(19) 0.41907(9) 0.0303(5) Uani 1 1 d . . . . .
C16 C 0.3809(4) 0.55815(19) 0.46156(9) 0.0318(5) Uani 1 1 d . . . . .
C17 C 0.3671(4) 0.6182(2) 0.50915(9) 0.0374(6) Uani 1 1 d . . . . .
H17 H 0.4559 0.6853 0.5157 0.045 Uiso 1 1 calc R U . . .
C18 C 0.2248(4) 0.5832(2) 0.54882(10) 0.0414(6) Uani 1 1 d . . . . .
H18 H 0.2170 0.6275 0.5814 0.050 Uiso 1 1 calc R U . . .
C19 C 0.0972(4) 0.4855(2) 0.54071(10) 0.0372(6) Uani 1 1 d . . . . .
H19 H 0.0002 0.4629 0.5674 0.045 Uiso 1 1 calc R U . . .
C20 C 0.1097(4) 0.4184(2) 0.49257(9) 0.0302(5) Uani 1 1 d . . . . .
C21 C -0.0156(4) 0.3154(2) 0.48321(11) 0.0375(6) Uani 1 1 d . . . . .
H21 H -0.1117 0.2907 0.5098 0.045 Uiso 1 1 calc R U . . .
C22 C -0.0018(4) 0.2510(2) 0.43702(10) 0.0409(6) Uani 1 1 d . . . . .
H22 H -0.0874 0.1820 0.4316 0.049 Uiso 1 1 calc R U . . .
C23 C 0.1383(4) 0.2863(2) 0.39745(10) 0.0378(6) Uani 1 1 d . . . . .
H23 H 0.1476 0.2408 0.3653 0.045 Uiso 1 1 calc R U . . .
C24 C 0.2618(4) 0.3852(2) 0.40440(9) 0.0327(5) Uani 1 1 d . . . . .
H24 H 0.3554 0.4082 0.3769 0.039 Uiso 1 1 calc R U . . .
C25 C 0.2521(4) 0.45465(19) 0.45234(9) 0.0296(5) Uani 1 1 d . . . . .
N1 N 0.4370(3) 0.64470(17) 0.37443(8) 0.0312(5) 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
C1 C2 1.418(3) . ?
C1 C6 1.425(3) . ?
C1 C10 1.433(3) . ?
C2 C3 1.371(4) . ?
C3 C4 1.398(4) . ?
C4 C5 1.350(4) . ?
C5 C6 1.424(4) . ?
C6 C7 1.400(4) . ?
C7 C8 1.370(4) . ?
C8 C9 1.400(4) . ?
C9 C10 1.368(3) . ?
C10 C11 1.488(3) . ?
C11 N1 1.348(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.383(4) . ?
C14 C15 1.383(3) . ?
C15 N1 1.348(3) . ?
C15 C16 1.494(3) . ?
C16 C17 1.364(3) . ?
C16 C25 1.430(3) . ?
C17 C18 1.407(4) . ?
C18 C19 1.371(4) . ?
C19 C20 1.415(3) . ?
C20 C21 1.413(3) . ?
C20 C25 1.421(3) . ?
C21 C22 1.358(3) . ?
C22 C23 1.397(4) . ?
C23 C24 1.361(3) . ?
C24 C25 1.423(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 118.5(2) . . ?
C2 C1 C10 123.1(2) . . ?
C6 C1 C10 118.4(2) . . ?
C3 C2 C1 120.5(2) . . ?
C2 C3 C4 120.8(3) . . ?
C5 C4 C3 120.3(3) . . ?
C4 C5 C6 121.2(3) . . ?
C7 C6 C5 121.7(2) . . ?
C7 C6 C1 119.7(2) . . ?
C5 C6 C1 118.6(3) . . ?
C8 C7 C6 120.9(2) . . ?
C7 C8 C9 119.8(3) . . ?
C10 C9 C8 121.7(2) . . ?
C9 C10 C1 119.5(2) . . ?
C9 C10 C11 119.0(2) . . ?
C1 C10 C11 121.5(2) . . ?
N1 C11 C12 122.1(2) . . ?
N1 C11 C10 116.97(19) . . ?
C12 C11 C10 121.0(2) . . ?
C13 C12 C11 119.2(2) . . ?
C12 C13 C14 118.9(2) . . ?
C13 C14 C15 119.0(2) . . ?
N1 C15 C14 122.6(2) . . ?
N1 C15 C16 115.6(2) . . ?
C14 C15 C16 121.8(2) . . ?
C17 C16 C25 119.3(2) . . ?
C17 C16 C15 120.7(2) . . ?
C25 C16 C15 120.1(2) . . ?
C16 C17 C18 121.7(2) . . ?
C19 C18 C17 120.3(2) . . ?
C18 C19 C20 120.1(2) . . ?
C21 C20 C19 121.8(2) . . ?
C21 C20 C25 118.7(2) . . ?
C19 C20 C25 119.5(2) . . ?
C22 C21 C20 121.4(2) . . ?
C21 C22 C23 120.0(2) . . ?
C24 C23 C22 120.8(2) . . ?
C23 C24 C25 120.7(2) . . ?
C20 C25 C24 118.3(2) . . ?
C20 C25 C16 119.2(2) . . ?
C24 C25 C16 122.5(2) . . ?
C15 N1 C11 118.1(2) . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-3

