# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C
# This journal is © The Royal Society of Chemistry 2013


data_global
_journal_name_full               J.Mat.Chem.C
_journal_coden_cambridge         1695
#TrackingRef 'Comp-14cifdoc.cif'

#------------------ AUDIT DETAILS -------------------------------------------#

_audit_creation_date             2010-11-10
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_update_record             ?

#------------------ SUBMISSION DETAILS --------------------------------------#

# Name and address of author for correspondence

_publ_contact_author_name        'ALLAIN, Magali'
_publ_contact_author_address     
;
MOLTECH ANJOU UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France

;
_publ_contact_author_email       magali.allain@univ-angers.fr
_publ_contact_author_fax         33(0)241735405
_publ_contact_author_phone       33(0)241735368
_publ_requested_coeditor_name    ?
_publ_contact_letter             # Include date of submission
;
Date of submission ?

Please consider this CIF submission for publication as a
Regular Structural Paper in Acta Crystallographica C.
;
_publ_requested_category         ?

#------------------ PROCESSING SUMMARY (JOURNAL OFFICE ONLY) ----------------#

_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?
_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?
_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#------------------ TITLE AND AUTHOR LIST------------------------------------#

_publ_section_title              
;
?
;

_publ_section_title_footnote     
;
?
;

loop_
_publ_author_address
;
MOLTECH ANJOU UMR CNRS 6200
2, bd Lavoisier
49045 Angers cedex
France
;

#------------------ TEXT ----------------------------------------------------#

_publ_section_synopsis           
;
# Insert blank lines between paragraphs
?
;
_publ_section_abstract           
;
# Insert blank lines between paragraphs
?
;

_publ_section_comment            
;
# Insert blank lines between paragraphs
?
;

_publ_section_exptl_prep         
;
?
;

_publ_section_exptl_refinement   
;
?
;

# Insert blank lines between references

_publ_section_references         
;
Allen, F.H., Kennard, O. & Taylor, R. (1983).
Acc. Chem. Res. 16, 146-153.

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A.
(1993) J. Appl. Cryst. 26, 343-350.

Altomare, A. Burla, M. C., Camalli, M., Cascarano, G. L.,
Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G.
& Spagna, R. (1999) J. Appl. Cryst. 32, 115-119.

Blessing, R. H. (1995) Acta Cryst., A51, 33-38.

Blessing, R. H. (1987) Cryst. Rev. 1, 3-58.

Blessing, R. H. (1989) J. Appl. Cryst. 22, 396-397.

Beurskens, P.T., Beurskens, G., de Gelder, R.,
Garci\'ia-Granda, S., Gould, R.O., Israel, R. & Smits, J.M.M.
(1999) The DIRDIF-99 program system,
Technical Report of the Crystallography Laboratory,
University of Nijmegen, The Netherlands.

Cremer, D. & Pople, J.A. (1975). J. Am. Chem. Soc. 97, 1354-1358.

Enraf-Nonius (1994). CAD4Express Software. Enraf-Nonius, Delft,
The Netherlands.

Farrugia, L. J. (1997) ORTEP-3 for Windows, J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999) WinGX, J. Appl. Cryst. 32, 837-838.

Flack, H.D. (1983). Acta Cryst. A39, 876-881.

Harms, K. & Wocadlo, S. (1995) XCAD-4. Program for Processing CAD-4
Diffractometer Data. University of Marburg, Germany.

Johnson, C.K. (1965). ORTEP. Report ORNL-3794. Oak Ridge National
Laboratory, Tennessee, USA.

Lehman, M. S. and Larsen, F. K. (1974) Acta. Cryst. A30, 580

LePage, Y. (1987). J. Appl. Cryst. 20, 264-269.

North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968) Acta Cryst,
A24, 351-359

Orpen, A. G., Brammer, L., Allen, F. H., Kennard, O., Watson, D. G.,
& Taylor, R. (1992). International Tables for Crystallography,
Volume C.

Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of G\"ottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of G\"ottingen, Germany.

Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.

Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of G\"ottingen, Germany.

Spek, A.L. (1990). Acta Cryst. A46, C34

Streltsov, V. A. & Zavodnik, V. E. (1989) Sov. Phys. Crystallogr.
34, 824-828

Streltsov, V. A. & Zavodnik, V. E. (1990) Sov. Phys. Crystallogr.
35, 281.

Walker, N. & Stuart, D. (1983). Acta Cryst., A39, 158 - 166.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
?
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;
_publ_author_name                M.ALLAIN

#------------------ SECTION 2. COMPOUND(S) DETAILS -------------------------#

data_sad
_database_code_depnum_ccdc_archive 'CCDC 905793'
#TrackingRef 'Comp-14cifdoc.cif'

_audit_creation_date             2010-11-10T12:23:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C11 H7 N1'
_chemical_formula_sum            'C11 H7 N'
_chemical_formula_weight         153.18

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
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                   9.6242(8)
_cell_length_b                   5.364(2)
_cell_length_c                   14.677(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.87(1)
_cell_angle_gamma                90
_cell_volume                     728.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2056
_cell_measurement_theta_min      4.06
_cell_measurement_theta_max      30

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.768
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2000))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            9620
_diffrn_reflns_av_R_equivalents  0.0664
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         4.06
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_full        30
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_reflns_number_total             2114
_reflns_number_gt                1033
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2f (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0389P)^2^+0.2522P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2114
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.067
_refine_ls_wR_factor_ref         0.1347
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.175

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.52706(19) 0.0313(4) 0.46089(13) 0.0355(5) Uani 1 d . . .
C2 C 0.48259(19) -0.1158(4) 0.37691(13) 0.0356(5) Uani 1 d . . .
C3 C 0.51436(19) -0.1137(4) 0.28540(13) 0.0363(5) Uani 1 d . . .
C4 C 0.5966(2) 0.0366(5) 0.24180(15) 0.0442(6) Uani 1 d . . .
C5 C 0.6023(2) -0.0185(5) 0.15087(16) 0.0495(6) Uani 1 d . . .
C6 C 0.5281(2) -0.2220(5) 0.10188(16) 0.0504(6) Uani 1 d . . .
C7 C 0.4448(3) -0.3727(5) 0.14134(15) 0.0490(6) Uani 1 d . . .
C8 C 0.4386(2) -0.3155(4) 0.23286(14) 0.0409(5) Uani 1 d . . .
C9 C 0.3874(2) -0.3154(4) 0.37424(13) 0.0396(5) Uani 1 d . . .
C10 C 0.3322(2) -0.3764(4) 0.45055(15) 0.0436(6) Uani 1 d . . .
C11 C 0.3754(2) -0.2365(4) 0.53079(15) 0.0416(5) Uani 1 d . . .
N1 N 0.3598(2) -0.4325(4) 0.28652(12) 0.0477(5) Uani 1 d . . .
H1 H 0.314(2) -0.584(5) 0.2748(15) 0.060(7) Uiso 1 d . . .
H4 H 0.650(2) 0.176(4) 0.2773(14) 0.044(6) Uiso 1 d . . .
H5 H 0.662(2) 0.092(4) 0.1213(15) 0.057(7) Uiso 1 d . . .
H6 H 0.535(2) -0.259(4) 0.0382(15) 0.053(6) Uiso 1 d . . .
H7 H 0.391(2) -0.516(4) 0.1072(15) 0.057(7) Uiso 1 d . . .
H10 H 0.267(2) -0.523(5) 0.4472(14) 0.059(7) Uiso 1 d . . .
H11 H 0.3413(19) -0.276(4) 0.5848(13) 0.038(5) Uiso 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0313(9) 0.0392(12) 0.0356(10) 0.0027(9) 0.0084(7) 0.0035(9)
C2 0.0339(10) 0.0368(12) 0.0352(10) 0.0026(9) 0.0079(8) 0.0020(9)
C3 0.0338(10) 0.0369(12) 0.0369(11) 0.0016(9) 0.0075(8) 0.0062(9)
C4 0.0452(12) 0.0444(14) 0.0441(13) 0.0013(11) 0.0139(10) 0.0011(11)
C5 0.0527(13) 0.0542(16) 0.0455(13) 0.0051(12) 0.0200(11) 0.0075(12)
C6 0.0561(13) 0.0591(17) 0.0373(12) -0.0020(12) 0.0152(10) 0.0121(13)
C7 0.0515(12) 0.0521(15) 0.0409(12) -0.0084(12) 0.0084(10) 0.0050(12)
C8 0.0371(10) 0.0416(13) 0.0418(11) -0.0005(10) 0.0072(8) 0.0036(10)
C9 0.0368(10) 0.0410(13) 0.0384(11) -0.0028(10) 0.0060(8) -0.0004(10)
C10 0.0415(11) 0.0436(14) 0.0462(13) -0.0015(11) 0.0125(9) -0.0083(11)
C11 0.0389(11) 0.0464(14) 0.0405(12) 0.0038(10) 0.0128(9) -0.0040(10)
N1 0.0507(11) 0.0449(13) 0.0466(11) -0.0101(9) 0.0116(8) -0.0122(10)

#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 C1 1.424(4) 3_656 ?
C1 C2 1.427(3) . ?
C1 C11 1.430(3) 3_656 ?
C2 C9 1.403(3) . ?
C2 C3 1.457(3) . ?
C3 C4 1.402(3) . ?
C3 C8 1.411(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.97(2) . ?
C5 C6 1.392(3) . ?
C5 H5 1.00(2) . ?
C6 C7 1.373(3) . ?
C6 H6 0.98(2) . ?
C7 C8 1.395(3) . ?
C7 H7 0.98(2) . ?
C8 N1 1.384(3) . ?
C9 N1 1.391(3) . ?
C9 C10 1.404(3) . ?
C10 C11 1.362(3) . ?
C10 H10 1.00(2) . ?
C11 C1 1.430(3) 3_656 ?
C11 H11 0.960(19) . ?
N1 H1 0.92(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
C1 C1 C2 118.4(2) 3_656 . ?
C1 C1 C11 119.3(2) 3_656 3_656 ?
C2 C1 C11 122.29(18) . 3_656 ?
C9 C2 C1 119.05(17) . . ?
C9 C2 C3 106.27(17) . . ?
C1 C2 C3 134.68(19) . . ?
C4 C3 C8 117.65(19) . . ?
C4 C3 C2 135.44(19) . . ?
C8 C3 C2 106.90(17) . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 121.8(12) . . ?
C3 C4 H4 118.6(12) . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 118.0(13) . . ?
C6 C5 H5 120.9(13) . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.1(13) . . ?
C5 C6 H6 119.6(13) . . ?
C6 C7 C8 117.4(2) . . ?
C6 C7 H7 122.0(13) . . ?
C8 C7 H7 120.6(13) . . ?
N1 C8 C7 128.5(2) . . ?
N1 C8 C3 108.59(17) . . ?
C7 C8 C3 122.9(2) . . ?
N1 C9 C2 109.19(18) . . ?
N1 C9 C10 128.0(2) . . ?
C2 C9 C10 122.86(19) . . ?
C11 C10 C9 117.9(2) . . ?
C11 C10 H10 121.1(12) . . ?
C9 C10 H10 120.9(12) . . ?
C10 C11 C1 122.4(2) . 3_656 ?
C10 C11 H11 120.0(12) . . ?
C1 C11 H11 117.6(11) 3_656 . ?
C8 N1 C9 109.02(18) . . ?
C8 N1 H1 127.2(14) . . ?
C9 N1 H1 122.2(14) . . ?

# Attachment 'Comp-15cifdoc.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2011-01-05 at 11:50:00
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\cifdoc.dat
# CIF files read : new struct

#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

data_new
_database_code_depnum_ccdc_archive 'CCDC 905794'
#TrackingRef 'Comp-15cifdoc.cif'

_audit_creation_date             2011-01-05T11:50:00-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C38 H46 N2'
_chemical_formula_sum            'C38 H46 N2'
_chemical_formula_weight         530.77

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
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                   15.341(3)
_cell_length_b                   12.123(1)
_cell_length_c                   8.5232(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.53(1)
_cell_angle_gamma                90
_cell_volume                     1574.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4237
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      27.6

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2000))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            12476
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.6
_diffrn_reflns_theta_full        27.6
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_reflns_number_total             3573
_reflns_number_gt                1913
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2f (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0422P)^2^+1.2158P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3573
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0761
_refine_ls_wR_factor_ref         0.1873
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.204

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.33696(18) 0.5234(2) 0.3563(3) 0.0476(7) Uani 1 d . . .
C2 C 0.2690(2) 0.5508(2) 0.4443(4) 0.0577(8) Uani 1 d . . .
H2 H 0.2642 0.5174 0.5412 0.069 Uiso 1 calc R . .
C3 C 0.2093(2) 0.6284(3) 0.3841(4) 0.0641(9) Uani 1 d . . .
H3 H 0.1628 0.6467 0.4403 0.077 Uiso 1 calc R . .
C4 C 0.2169(2) 0.6804(3) 0.2401(4) 0.0668(9) Uani 1 d . . .
H4 H 0.176 0.7334 0.2024 0.08 Uiso 1 calc R . .
C5 C 0.28429(19) 0.6540(2) 0.1533(4) 0.0558(8) Uani 1 d . . .
H5 H 0.289 0.6897 0.058 0.067 Uiso 1 calc R . .
C6 C 0.34597(17) 0.5735(2) 0.2083(3) 0.0438(6) Uani 1 d . . .
C7 C 0.42172(17) 0.5230(2) 0.1504(3) 0.0416(6) Uani 1 d . . .
C8 C 0.45480(17) 0.4467(2) 0.2664(3) 0.0432(6) Uani 1 d . . .
C9 C 0.46244(16) 0.5335(2) 0.0082(3) 0.0412(6) Uani 1 d . . .
C10 C 0.43050(18) 0.6069(2) -0.1159(3) 0.0472(7) Uani 1 d . . .
H10 H 0.3809 0.649 -0.1048 0.057 Uiso 1 calc R . .
C11 C 0.47026(17) 0.6176(2) -0.2507(3) 0.0479(7) Uani 1 d . . .
H11 H 0.4483 0.6661 -0.3301 0.057 Uiso 1 calc R . .
C12 C 0.4112(2) 0.3684(2) 0.5197(3) 0.0532(7) Uani 1 d . . .
H12A H 0.3813 0.3979 0.6049 0.064 Uiso 1 calc R . .
H12B H 0.4726 0.3592 0.5593 0.064 Uiso 1 calc R . .
C13 C 0.3727(2) 0.2566(2) 0.4732(4) 0.0561(8) Uani 1 d . . .
H13A H 0.4047 0.2264 0.3913 0.067 Uiso 1 calc R . .
H13B H 0.3826 0.2081 0.5639 0.067 Uiso 1 calc R . .
C14 C 0.2760(2) 0.2542(2) 0.4143(4) 0.0595(8) Uani 1 d . . .
H14A H 0.2663 0.2938 0.3149 0.071 Uiso 1 calc R . .
H14B H 0.2436 0.2918 0.4897 0.071 Uiso 1 calc R . .
C15 C 0.2414(2) 0.1373(3) 0.3906(4) 0.0693(9) Uani 1 d . . .
H15A H 0.2754 0.0996 0.3176 0.083 Uiso 1 calc R . .
H15B H 0.2507 0.0986 0.4908 0.083 Uiso 1 calc R . .
C16 C 0.1468(2) 0.1301(3) 0.3293(5) 0.0797(11) Uani 1 d . . .
H16A H 0.1381 0.1659 0.2269 0.096 Uiso 1 calc R . .
H16B H 0.1132 0.1706 0.3998 0.096 Uiso 1 calc R . .
C17 C 0.1107(3) 0.0122(3) 0.3120(6) 0.0928(13) Uani 1 d . . .
H17A H 0.1436 -0.0283 0.2403 0.111 Uiso 1 calc R . .
H17B H 0.1196 -0.0241 0.414 0.111 Uiso 1 calc R . .
C18 C 0.0165(3) 0.0075(5) 0.2526(8) 0.1310(19) Uani 1 d . . .
H18A H 0.0075 0.0438 0.1506 0.157 Uiso 1 calc R . .
H18B H -0.0164 0.0481 0.3244 0.157 Uiso 1 calc R . .
C19 C -0.0195(4) -0.1089(5) 0.2355(9) 0.163(3) Uani 1 d . . .
H19A H 0.004 -0.1449 0.1491 0.245 Uiso 1 calc R . .
H19B H -0.0823 -0.1063 0.2153 0.245 Uiso 1 calc R . .
H19C H -0.0029 -0.1492 0.3311 0.245 Uiso 1 calc R . .
N1 N 0.40415(15) 0.44749(18) 0.3902(3) 0.0482(6) Uani 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0497(16) 0.0380(14) 0.0538(16) -0.0056(12) 0.0005(13) -0.0068(12)
C2 0.0629(19) 0.0489(17) 0.0621(18) -0.0052(14) 0.0100(15) -0.0054(15)
C3 0.0587(19) 0.062(2) 0.072(2) -0.0099(17) 0.0123(16) 0.0025(16)
C4 0.0590(19) 0.059(2) 0.082(2) -0.0008(17) 0.0078(17) 0.0150(16)
C5 0.0564(18) 0.0444(16) 0.0659(18) 0.0016(14) 0.0039(15) 0.0058(14)
C6 0.0433(15) 0.0319(13) 0.0543(16) -0.0042(12) -0.0026(12) -0.0042(11)
C7 0.0414(14) 0.0321(13) 0.0487(14) -0.0018(11) -0.0059(11) -0.0024(11)
C8 0.0441(14) 0.0358(13) 0.0478(14) -0.0004(11) -0.0028(12) -0.0042(12)
C9 0.0403(13) 0.0322(13) 0.0489(14) 0.0018(11) -0.0045(11) -0.0044(11)
C10 0.0423(14) 0.0400(14) 0.0573(17) 0.0052(12) -0.0028(12) 0.0025(12)
C11 0.0476(15) 0.0415(15) 0.0517(16) 0.0086(12) -0.0067(13) 0.0017(12)
C12 0.0588(18) 0.0527(17) 0.0457(15) 0.0088(13) -0.0043(13) -0.0015(14)
C13 0.0638(19) 0.0446(16) 0.0582(17) 0.0119(14) -0.0006(14) -0.0030(14)
C14 0.0636(19) 0.0470(17) 0.0669(19) 0.0052(14) 0.0030(15) -0.0051(15)
C15 0.065(2) 0.0540(19) 0.086(2) 0.0015(17) -0.0003(18) -0.0096(16)
C16 0.070(2) 0.070(2) 0.097(3) 0.006(2) -0.001(2) -0.0086(19)
C17 0.075(3) 0.077(3) 0.126(3) -0.008(2) 0.011(2) -0.017(2)
C18 0.090(3) 0.117(4) 0.181(5) -0.005(4) -0.005(3) -0.027(3)
C19 0.119(4) 0.119(5) 0.250(8) -0.036(5) 0.015(5) -0.062(4)
N1 0.0536(14) 0.0414(13) 0.0487(13) 0.0034(10) 0.0015(11) -0.0006(11)

#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 1.388(3) . ?
C1 C2 1.392(4) . ?
C1 C6 1.420(4) . ?
C2 C3 1.371(4) . ?
C2 H2 0.93 . ?
C3 C4 1.397(5) . ?
C3 H3 0.93 . ?
C4 C5 1.375(4) . ?
C4 H4 0.93 . ?
C5 C6 1.403(4) . ?
C5 H5 0.93 . ?
C6 C7 1.449(4) . ?
C7 C8 1.406(4) . ?
C7 C9 1.431(4) . ?
C8 N1 1.380(3) . ?
C8 C11 1.408(4) 3_665 ?
C9 C10 1.426(3) . ?
C9 C9 1.430(5) 3_665 ?
C10 C11 1.366(4) . ?
C10 H10 0.93 . ?
C11 C8 1.408(4) 3_665 ?
C11 H11 0.93 . ?
C12 N1 1.458(3) . ?
C12 C13 1.513(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.511(4) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 C15 1.519(4) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 C16 1.488(5) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 C17 1.534(5) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 C18 1.477(6) . ?
C17 H17A 0.97 . ?
C17 H17B 0.97 . ?
C18 C19 1.516(6) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?

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 129.1(3) . . ?
N1 C1 C6 108.9(2) . . ?
C2 C1 C6 122.1(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120 . . ?
C6 C5 H5 120 . . ?
C5 C6 C1 117.7(3) . . ?
C5 C6 C7 135.8(3) . . ?
C1 C6 C7 106.5(2) . . ?
C8 C7 C9 119.8(2) . . ?
C8 C7 C6 106.1(2) . . ?
C9 C7 C6 134.0(2) . . ?
N1 C8 C7 110.1(2) . . ?
N1 C8 C11 127.9(2) . 3_665 ?
C7 C8 C11 122.0(2) . 3_665 ?
C10 C9 C9 119.7(3) . 3_665 ?
C10 C9 C7 122.5(2) . . ?
C9 C9 C7 117.8(3) 3_665 . ?
C11 C10 C9 122.3(2) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C8 118.4(2) . 3_665 ?
C10 C11 H11 120.8 . . ?
C8 C11 H11 120.8 3_665 . ?
N1 C12 C13 113.4(2) . . ?
N1 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
N1 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
C14 C13 C12 116.3(3) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C15 112.1(3) . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 114.4(3) . . ?
C16 C15 H15A 108.7 . . ?
C14 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
C14 C15 H15B 108.7 . . ?
H15A C15 H15B 107.6 . . ?
C15 C16 C17 114.6(3) . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16B 108.6 . . ?
C17 C16 H16B 108.6 . . ?
H16A C16 H16B 107.6 . . ?
C18 C17 C16 113.5(4) . . ?
C18 C17 H17A 108.9 . . ?
C16 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 C19 113.6(5) . . ?
C17 C18 H18A 108.8 . . ?
C19 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C19 C18 H18B 108.8 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C1 108.4(2) . . ?
C8 N1 C12 125.1(2) . . ?
C1 N1 C12 125.7(2) . . ?

# Attachment 'Comp-16cifdoc.cif'

#\#CIF_1.1

# CIF produced by WinGX routine CIF_UPDATE
# Created on 2011-10-03 at 11:08:59
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.4
# Request file : c:\wingx\files\cifdoc.dat
# CIF files read : sad struct

#------------------ SECTION 1. GLOBAL INFORMATION ---------------------------#

data_sad1
_database_code_depnum_ccdc_archive 'CCDC 905795'
#TrackingRef 'Comp-16cifdoc.cif'

_audit_creation_date             2011-10-03T11:08:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C42 H38 N2'
_chemical_formula_sum            'C42 H38 N2'
_chemical_formula_weight         570.74

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6871(5)
_cell_length_b                   9.4028(6)
_cell_length_c                   11.9518(9)
_cell_angle_alpha                68.803(5)
_cell_angle_beta                 87.124(6)
_cell_angle_gamma                73.605(6)
_cell_volume                     771.38(9)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6338
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      30

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            27407
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.12
_diffrn_reflns_theta_max         30
_diffrn_reflns_theta_full        30
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_reflns_number_total             4465
_reflns_number_gt                2551
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2g (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+0.3363P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4465
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1446
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.214

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.0137(2) 0.99906(18) -0.05948(14) 0.0324(3) Uani 1 d . . .
C2 C 0.1128(2) 0.85500(19) -0.07500(16) 0.0371(4) Uani 1 d . . .
C3 C 0.1792(2) 0.7159(2) 0.02044(16) 0.0385(4) Uani 1 d . . .
C4 C 0.1503(2) 0.71715(18) 0.13692(15) 0.0346(4) Uani 1 d . . .
C5 C 0.0591(2) 0.85554(18) 0.15861(15) 0.0328(4) Uani 1 d . . .
C6 C 0.0630(2) 0.81224(19) 0.28825(15) 0.0338(4) Uani 1 d . . .
C7 C 0.1580(2) 0.64832(19) 0.33889(15) 0.0359(4) Uani 1 d . . .
C8 C -0.0059(3) 0.8918(2) 0.36669(16) 0.0414(4) Uani 1 d . . .
C9 C 0.0191(3) 0.8099(2) 0.48979(17) 0.0483(5) Uani 1 d . . .
C10 C 0.1153(3) 0.6496(2) 0.53669(17) 0.0473(5) Uani 1 d . . .
C11 C 0.1861(3) 0.5663(2) 0.46267(16) 0.0433(4) Uani 1 d . . .
C12 C 0.2848(2) 0.42729(18) 0.26101(15) 0.0366(4) Uani 1 d . . .
C13 C 0.1969(2) 0.3572(2) 0.20619(17) 0.0410(4) Uani 1 d . . .
C14 C 0.2665(3) 0.1976(2) 0.22350(17) 0.0417(4) Uani 1 d . . .
C15 C 0.4235(2) 0.10359(19) 0.29627(16) 0.0384(4) Uani 1 d . . .
C16 C 0.5089(2) 0.1755(2) 0.35069(17) 0.0424(4) Uani 1 d . . .
C17 C 0.4424(2) 0.3363(2) 0.33284(17) 0.0420(4) Uani 1 d . . .
C18 C 0.4971(3) -0.0716(2) 0.31473(18) 0.0452(4) Uani 1 d . . .
C19 C 0.5415(3) -0.1030(2) 0.19863(18) 0.0450(4) Uani 1 d . . .
C20 C 0.6309(3) -0.2776(2) 0.2209(2) 0.0508(5) Uani 1 d . . .
C21 C 0.6712(4) -0.3122(4) 0.1061(3) 0.0700(7) Uani 1 d . . .
N1 N 0.2095(2) 0.59088(16) 0.24626(12) 0.0388(3) Uani 1 d . . .
H2 H 0.135(2) 0.856(2) -0.1576(17) 0.041(5) Uiso 1 d . . .
H3 H 0.247(3) 0.620(2) 0.0052(17) 0.047(5) Uiso 1 d . . .
H8 H -0.077(3) 1.004(2) 0.3344(18) 0.051(5) Uiso 1 d . . .
H9 H -0.035(3) 0.865(3) 0.546(2) 0.063(6) Uiso 1 d . . .
H10 H 0.126(3) 0.595(3) 0.622(2) 0.067(7) Uiso 1 d . . .
H11 H 0.246(3) 0.456(2) 0.4933(17) 0.048(5) Uiso 1 d . . .
H13 H 0.085(3) 0.418(2) 0.1584(18) 0.048(5) Uiso 1 d . . .
H14 H 0.203(3) 0.151(2) 0.1831(18) 0.054(6) Uiso 1 d . . .
H16 H 0.620(3) 0.111(2) 0.4029(18) 0.055(6) Uiso 1 d . . .
H17 H 0.503(3) 0.386(2) 0.3721(19) 0.059(6) Uiso 1 d . . .
H18A H 0.609(3) -0.119(2) 0.3693(19) 0.055(6) Uiso 1 d . . .
H18B H 0.405(3) -0.130(2) 0.3575(19) 0.060(6) Uiso 1 d . . .
H19A H 0.624(3) -0.040(3) 0.152(2) 0.060(6) Uiso 1 d . . .
H19B H 0.432(3) -0.062(2) 0.1416(19) 0.054(6) Uiso 1 d . . .
H20A H 0.754(3) -0.317(3) 0.273(2) 0.077(7) Uiso 1 d . . .
H20B H 0.557(3) -0.340(3) 0.270(2) 0.063(6) Uiso 1 d . . .
H21A H 0.760(5) -0.254(4) 0.060(3) 0.114(11) Uiso 1 d . . .
H21B H 0.727(4) -0.426(4) 0.124(3) 0.105(10) Uiso 1 d . . .
H21C H 0.564(4) -0.276(3) 0.055(3) 0.091(9) Uiso 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0322(8) 0.0278(7) 0.0355(8) -0.0123(7) -0.0022(6) -0.0042(6)
C2 0.0420(9) 0.0331(9) 0.0337(9) -0.0141(7) -0.0004(7) -0.0038(7)
C3 0.0434(9) 0.0306(8) 0.0380(9) -0.0148(7) -0.0001(7) -0.0016(7)
C4 0.0376(9) 0.0278(8) 0.0351(9) -0.0116(7) -0.0034(7) -0.0030(7)
C5 0.0333(8) 0.0299(8) 0.0337(8) -0.0125(7) -0.0003(6) -0.0052(6)
C6 0.0354(8) 0.0316(8) 0.0341(9) -0.0125(7) -0.0016(6) -0.0077(7)
C7 0.0394(9) 0.0303(8) 0.0373(9) -0.0136(7) -0.0022(7) -0.0064(7)
C8 0.0501(10) 0.0337(9) 0.0379(10) -0.0146(8) 0.0004(8) -0.0056(8)
C9 0.0663(13) 0.0395(10) 0.0379(10) -0.0175(8) 0.0028(9) -0.0088(9)
C10 0.0643(12) 0.0398(10) 0.0335(10) -0.0102(8) -0.0031(9) -0.0115(9)
C11 0.0544(11) 0.0320(9) 0.0373(10) -0.0095(7) -0.0041(8) -0.0057(8)
C12 0.0420(9) 0.0262(8) 0.0365(9) -0.0104(7) -0.0009(7) -0.0027(7)
C13 0.0395(9) 0.0357(9) 0.0422(10) -0.0130(8) -0.0074(8) -0.0018(7)
C14 0.0448(10) 0.0345(9) 0.0456(10) -0.0164(8) -0.0064(8) -0.0069(8)
C15 0.0428(9) 0.0298(8) 0.0393(9) -0.0120(7) 0.0007(7) -0.0056(7)
C16 0.0418(10) 0.0322(9) 0.0453(10) -0.0124(8) -0.0091(8) 0.0011(7)
C17 0.0442(10) 0.0342(9) 0.0461(10) -0.0162(8) -0.0073(8) -0.0051(8)
C18 0.0521(11) 0.0296(9) 0.0485(11) -0.0122(8) -0.0017(9) -0.0055(8)
C19 0.0498(11) 0.0323(9) 0.0480(11) -0.0136(8) 0.0011(9) -0.0052(8)
C20 0.0587(13) 0.0347(10) 0.0579(13) -0.0187(9) 0.0044(10) -0.0091(9)
C21 0.0668(16) 0.0703(17) 0.0814(18) -0.0476(15) 0.0006(15) -0.0053(14)
N1 0.0489(8) 0.0273(7) 0.0330(8) -0.0102(6) -0.0043(6) -0.0001(6)

#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 1.426(2) . ?
C1 C5 1.431(2) 2_575 ?
C1 C1 1.433(3) 2_575 ?
C2 C3 1.370(2) . ?
C2 H2 0.989(19) . ?
C3 C4 1.403(2) . ?
C3 H3 0.98(2) . ?
C4 N1 1.399(2) . ?
C4 C5 1.401(2) . ?
C5 C1 1.431(2) 2_575 ?
C5 C6 1.452(2) . ?
C6 C8 1.397(2) . ?
C6 C7 1.418(2) . ?
C7 N1 1.394(2) . ?
C7 C11 1.394(2) . ?
C8 C9 1.386(3) . ?
C8 H8 0.98(2) . ?
C9 C10 1.391(3) . ?
C9 H9 1.00(2) . ?
C10 C11 1.380(3) . ?
C10 H10 0.96(2) . ?
C11 H11 0.95(2) . ?
C12 C17 1.388(2) . ?
C12 C13 1.389(2) . ?
C12 N1 1.430(2) . ?
C13 C14 1.383(2) . ?
C13 H13 0.96(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.98(2) . ?
C15 C16 1.387(3) . ?
C15 C18 1.519(2) . ?
C16 C17 1.391(2) . ?
C16 H16 0.98(2) . ?
C17 H17 0.98(2) . ?
C18 C19 1.523(3) . ?
C18 H18A 0.99(2) . ?
C18 H18B 1.02(2) . ?
C19 C20 1.518(3) . ?
C19 H19A 1.00(2) . ?
C19 H19B 1.00(2) . ?
C20 C21 1.519(3) . ?
C20 H20A 1.06(2) . ?
C20 H20B 0.96(2) . ?
C21 H21A 1.01(3) . ?
C21 H21B 0.98(3) . ?
C21 H21C 0.96(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 C5 122.66(15) . 2_575 ?
C2 C1 C1 119.46(18) . 2_575 ?
C5 C1 C1 117.88(17) 2_575 2_575 ?
C3 C2 C1 122.20(16) . . ?
C3 C2 H2 119.1(10) . . ?
C1 C2 H2 118.7(10) . . ?
C2 C3 C4 118.34(16) . . ?
C2 C3 H3 119.1(11) . . ?
C4 C3 H3 122.5(11) . . ?
N1 C4 C5 109.67(14) . . ?
N1 C4 C3 127.88(15) . . ?
C5 C4 C3 122.40(15) . . ?
C4 C5 C1 119.68(15) . 2_575 ?
C4 C5 C6 106.55(14) . . ?
C1 C5 C6 133.77(15) 2_575 . ?
C8 C6 C7 117.94(16) . . ?
C8 C6 C5 135.24(15) . . ?
C7 C6 C5 106.81(14) . . ?
N1 C7 C11 128.82(15) . . ?
N1 C7 C6 108.85(14) . . ?
C11 C7 C6 122.32(16) . . ?
C9 C8 C6 119.86(17) . . ?
C9 C8 H8 120.2(12) . . ?
C6 C8 H8 119.9(12) . . ?
C8 C9 C10 120.82(18) . . ?
C8 C9 H9 120.2(13) . . ?
C10 C9 H9 118.9(13) . . ?
C11 C10 C9 121.33(18) . . ?
C11 C10 H10 119.8(14) . . ?
C9 C10 H10 118.8(14) . . ?
C10 C11 C7 117.71(17) . . ?
C10 C11 H11 122.2(12) . . ?
C7 C11 H11 120.0(12) . . ?
C17 C12 C13 119.57(15) . . ?
C17 C12 N1 120.46(16) . . ?
C13 C12 N1 119.95(15) . . ?
C14 C13 C12 119.98(16) . . ?
C14 C13 H13 119.8(12) . . ?
C12 C13 H13 120.2(12) . . ?
C13 C14 C15 121.45(17) . . ?
C13 C14 H14 118.6(12) . . ?
C15 C14 H14 119.9(12) . . ?
C16 C15 C14 117.76(16) . . ?
C16 C15 C18 121.61(16) . . ?
C14 C15 C18 120.63(17) . . ?
C15 C16 C17 121.59(16) . . ?
C15 C16 H16 119.1(12) . . ?
C17 C16 H16 119.3(12) . . ?
C12 C17 C16 119.65(17) . . ?
C12 C17 H17 119.1(12) . . ?
C16 C17 H17 121.2(12) . . ?
C15 C18 C19 113.83(16) . . ?
C15 C18 H18A 109.2(12) . . ?
C19 C18 H18A 108.9(12) . . ?
C15 C18 H18B 109.2(12) . . ?
C19 C18 H18B 109.1(12) . . ?
H18A C18 H18B 106.4(17) . . ?
C20 C19 C18 112.53(16) . . ?
C20 C19 H19A 108.5(12) . . ?
C18 C19 H19A 110.5(12) . . ?
C20 C19 H19B 110.1(12) . . ?
C18 C19 H19B 112.2(12) . . ?
H19A C19 H19B 102.5(17) . . ?
C19 C20 C21 113.4(2) . . ?
C19 C20 H20A 109.6(13) . . ?
C21 C20 H20A 108.3(13) . . ?
C19 C20 H20B 109.5(13) . . ?
C21 C20 H20B 111.1(13) . . ?
H20A C20 H20B 104.6(18) . . ?
C20 C21 H21A 109.7(18) . . ?
C20 C21 H21B 111.0(18) . . ?
H21A C21 H21B 108(2) . . ?
C20 C21 H21C 111.5(17) . . ?
H21A C21 H21C 107(2) . . ?
H21B C21 H21C 110(2) . . ?
C7 N1 C4 108.13(13) . . ?
C7 N1 C12 125.52(14) . . ?
C4 N1 C12 125.73(14) . . ?