# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_she1013
_database_code_depnum_ccdc_archive 'CCDC 2005761'
loop_
_audit_author_name
_audit_author_address
'Anthony C. Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             10-05-05
_audit_creation_method           CRYSTALS_ver_12.87

_oxford_structure_analysis_title '5051451 she1013, scalepacked, 25 deg'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.0517(3)
_cell_length_b                   11.6821(6)
_cell_length_c                   12.7352(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1495.43(12)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C9 H8 N2 
# Dc =      1.28 Fooo =    608.00 Mu =      0.79 M =    144.18
# Found Formula = C9 H8 N2 
# Dc =      1.28 FOOO =    608.00 Mu =      0.79 M =    144.18

_chemical_formula_sum            'C9 H8 N2'
_chemical_formula_moiety         'C9 H8 N2'
_chemical_compound_source        local
_chemical_formula_weight         144.18


_cell_measurement_reflns_used    11875
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5
_cell_measurement_temperature    200

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_max          0.260

_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.079

# Sheldrick geometric approximatio 0.99 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.874 # .998*8.89/10.15    0.99 
_exptl_absorpt_correction_T_max  0.998 # 1.00 
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ' φ and ω scans with CCD '
_diffrn_special_details          
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 360 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 90 percent of data collected with 4-fold  
redundancy or more.
;

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      200
_diffrn_reflns_number            16877
_reflns_number_total             1312
_diffrn_reflns_av_R_equivalents  0.077
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1312 
# Theoretical number of reflections is about 2635 


_diffrn_reflns_theta_min         3.116
_diffrn_reflns_theta_max         25.005
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        25.005
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              0
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.26
_oxford_diffrn_Wilson_scale      4.93

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.31


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     0
_refine_ls_number_parameters     124
_oxford_refine_ls_R_factor_ref   0.0599
_refine_ls_wR_factor_ref         0.1028
_refine_ls_goodness_of_fit_ref   1.0478
_refine_ls_shift/su_max          0.0007935
_refine_ls_shift/su_mean         0.00003 # 2.5070903 


# The values computed from all data 
_oxford_reflns_number_all        1312
_refine_ls_R_factor_all          0.0599
_refine_ls_wR_factor_all         0.1028

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1045
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_gt          0.0961

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.59P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

_refine_special_details          
;
The crystals supplied were all very thin plates.
Intensity data were scaled by multi-scan inter-frame methods 
(DENZO/SCALEPACK, Otwinowski & Minor, 1997) to correct 
for absorption arising from the fibre and oil used to mount the sample. 


The H atoms were all observed in a difference map, 
but were introduced at geometrically determined positions. 
They were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined without restraints
and the displacement parameters were held fixed. 


The largest peaks in the final difference electron density map 
are located between molecules.


;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.72054(18) 0.45408(16) 0.45043(15) 0.0365 1.0000 Uani . . . . . . .
C2 C 0.63584(18) 0.52559(15) 0.37845(16) 0.0376 1.0000 Uani . . . . . . .
C3 C 0.68878(18) 0.52181(16) 0.28350(15) 0.0359 1.0000 Uani . . . . . . .
C4 C 0.81217(17) 0.44755(15) 0.28972(15) 0.0333 1.0000 Uani . . . . . . .
C5 C 0.85873(18) 0.47276(18) 0.40151(16) 0.0385 1.0000 Uani . . . . . . .
N6 N 0.44682(15) 0.26832(16) 0.41564(13) 0.0461 1.0000 Uani . . . . . . .
C7 C 0.55654(17) 0.29374(16) 0.41769(13) 0.0329 1.0000 Uani . . . . . . .
C8 C 0.69732(15) 0.32612(15) 0.41789(14) 0.0296 1.0000 Uani . . . . . . .
C9 C 0.76372(16) 0.32104(15) 0.30609(13) 0.0292 1.0000 Uani . . . . . . .
C10 C 0.67549(16) 0.27877(16) 0.22332(14) 0.0333 1.0000 Uani . . . . . . .
N11 N 0.60454(16) 0.24578(16) 0.16037(13) 0.0480 1.0000 Uani . . . . . . .
H11 H 0.7147(18) 0.4637(16) 0.5278(16) 0.0419 1.0000 Uiso . . . . . . .
H21 H 0.5543(19) 0.5613(17) 0.3961(15) 0.0422 1.0000 Uiso . . . . . . .
H31 H 0.6558(18) 0.5499(17) 0.2181(16) 0.0413 1.0000 Uiso . . . . . . .
H41 H 0.8755(18) 0.4543(16) 0.2329(15) 0.0369 1.0000 Uiso . . . . . . .
H52 H 0.8904(18) 0.5529(19) 0.4083(16) 0.0433 1.0000 Uiso . . . . . . .
H51 H 0.9257(19) 0.4197(17) 0.4288(15) 0.0425 1.0000 Uiso . . . . . . .
H81 H 0.7440(17) 0.2729(15) 0.4662(14) 0.0335 1.0000 Uiso . . . . . . .
H91 H 0.8413(18) 0.2699(16) 0.3087(13) 0.0333 1.0000 Uiso . . . . . . .

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 0.0381(10) 0.0400(11) 0.0314(10) -0.0077(8) -0.0036(8) -0.0026(8)
C2 0.0327(10) 0.0272(9) 0.0530(13) -0.0058(8) 0.0001(8) 0.0037(8)
C3 0.0367(10) 0.0285(9) 0.0424(11) 0.0053(8) -0.0040(8) -0.0026(7)
C4 0.0269(9) 0.0336(10) 0.0393(10) 0.0007(8) 0.0058(8) -0.0044(7)
C5 0.0297(9) 0.0325(10) 0.0533(12) -0.0050(9) -0.0094(8) -0.0055(8)
N6 0.0309(8) 0.0670(12) 0.0405(9) 0.0091(8) 0.0018(7) -0.0077(8)
C7 0.0338(10) 0.0398(11) 0.0250(9) 0.0040(7) 0.0003(8) 0.0001(8)
C8 0.0254(8) 0.0338(10) 0.0295(9) 0.0036(8) -0.0047(7) -0.0006(7)
C9 0.0225(8) 0.0292(9) 0.0358(10) -0.0026(8) -0.0008(7) 0.0013(7)
C10 0.0262(8) 0.0395(10) 0.0344(10) -0.0050(8) 0.0046(8) 0.0004(7)
N11 0.0371(8) 0.0670(12) 0.0398(10) -0.0160(9) -0.0010(8) -0.0051(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5070(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.504(3) yes
C1 . C5 . 1.538(3) yes
C1 . C8 . 1.569(2) yes
C1 . H11 . 0.99(2) no
C2 . C3 . 1.322(3) yes
C2 . H21 . 0.947(19) no
C3 . C4 . 1.516(3) yes
C3 . H31 . 0.95(2) no
C4 . C5 . 1.527(3) yes
C4 . C9 . 1.570(2) yes
C4 . H41 . 0.967(19) no
C5 . H52 . 0.99(2) no
C5 . H51 . 0.98(2) no
N6 . C7 . 1.142(2) yes
C7 . C8 . 1.465(2) yes
C8 . C9 . 1.574(2) yes
C8 . H81 . 0.992(18) no
C9 . C10 . 1.463(2) yes
C9 . H91 . 0.983(18) no
C10 . N11 . 1.140(2) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C5 . 100.69(16) yes
C2 . C1 . C8 . 106.50(14) yes
C5 . C1 . C8 . 99.36(14) yes
C2 . C1 . H11 . 120.5(11) no
C5 . C1 . H11 . 116.1(11) no
C8 . C1 . H11 . 111.2(11) no
C1 . C2 . C3 . 108.12(16) yes
C1 . C2 . H21 . 126.2(12) no
C3 . C2 . H21 . 125.4(12) no
C2 . C3 . C4 . 107.50(17) yes
C2 . C3 . H31 . 130.3(11) no
C4 . C3 . H31 . 121.8(12) no
C3 . C4 . C5 . 100.90(15) yes
C3 . C4 . C9 . 106.97(13) yes
C5 . C4 . C9 . 98.79(14) yes
C3 . C4 . H41 . 117.0(11) no
C5 . C4 . H41 . 118.7(11) no
C9 . C4 . H41 . 112.3(11) no
C1 . C5 . C4 . 94.22(13) yes
C1 . C5 . H52 . 112.8(11) no
C4 . C5 . H52 . 111.2(12) no
C1 . C5 . H51 . 112.8(11) no
C4 . C5 . H51 . 114.8(11) no
H52 . C5 . H51 . 110.3(15) no
N6 . C7 . C8 . 178.79(19) yes
C1 . C8 . C7 . 112.97(14) yes
C1 . C8 . C9 . 102.23(13) yes
C7 . C8 . C9 . 113.48(14) yes
C1 . C8 . H81 . 111.3(10) no
C7 . C8 . H81 . 107.2(10) no
C9 . C8 . H81 . 109.7(10) no
C4 . C9 . C8 . 102.49(13) yes
C4 . C9 . C10 . 114.21(15) yes
C8 . C9 . C10 . 114.04(13) yes
C4 . C9 . H91 . 109.3(10) no
C8 . C9 . H91 . 109.2(10) no
C10 . C9 . H91 . 107.4(10) no
C9 . C10 . N11 . 178.52(17) yes




#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N6 C10 3.253(2) . 8_455 no
N6 C9 3.426(2) . 8_455 no
N6 C8 3.464(2) . 4_456 no
N6 N11 3.501(2) . 5 no
N6 N11 3.584(2) . 8_455 no
N11 C7 3.162(2) . 5_554 no
N11 C8 3.333(2) . 5_554 no
N11 C9 3.562(2) . 8_455 no
N11 C2 3.564(2) . 6_645 no
C3 C10 3.385(3) . 3_655 no
C3 C9 3.540(3) . 3_655 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . -0.4(2) no
C1 C5 C4 C3 . . . . 48.4(2) no
C1 C5 C4 C9 . . . . -60.9(1) no
C1 C8 C9 C4 . . . . -1.3(2) no
C1 C8 C9 C10 . . . . -125.3(2) no
C2 C1 C5 C4 . . . . -48.6(2) no
C2 C1 C8 C7 . . . . -54.3(2) no
C2 C1 C8 C9 . . . . 68.0(2) no
C2 C3 C4 C5 . . . . -32.2(2) no
C2 C3 C4 C9 . . . . 70.6(2) no
C3 C2 C1 C5 . . . . 32.6(2) no
C3 C2 C1 C8 . . . . -70.7(2) no
C3 C4 C9 C8 . . . . -65.7(2) no
C3 C4 C9 C10 . . . . 58.2(2) no
C4 C5 C1 C8 . . . . 60.3(2) no
C4 C9 C8 C7 . . . . 120.6(2) no
C5 C1 C8 C7 . . . . -158.5(2) no
C5 C1 C8 C9 . . . . -36.1(2) no
C5 C4 C9 C8 . . . . 38.6(1) no
C5 C4 C9 C10 . . . . 162.5(1) no
C7 C8 C9 C10 . . . . -3.3(2) no
####################################################################### 
# 
# 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_she1014
_database_code_depnum_ccdc_archive 'CCDC 2005762'
loop_
_audit_author_name
_audit_author_address
'Anthony C. Willis'
;Australian National University
Australia
;
_audit_update_record             
;
2020-05-25 deposited with the CCDC.	2020-10-02 downloaded from the CCDC.
;
_audit_creation_date             10-05-05
_audit_creation_method           CRYSTALS_ver_12.87

_oxford_structure_analysis_title '5051510 she1014'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.7110(2)
_cell_length_b                   8.0661(2)
_cell_length_c                   12.5023(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     777.61(3)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C9 H8 N2 
# Dc =      1.23 Fooo =    304.00 Mu =      0.76 M =    144.18
# Found Formula = C9 H8 N2 
# Dc =      1.23 FOOO =    304.00 Mu =      0.76 M =    144.18

_chemical_formula_sum            'C9 H8 N2'
_chemical_formula_moiety         'C9 H8 N2'
_chemical_compound_source        local
_chemical_formula_weight         144.18


_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    200

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.110
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_max          0.520

_exptl_crystal_density_diffrn    1.231
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.076

# Sheldrick geometric approximatio 0.99 0.99 
# Absorption correction 

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.050
0 0 -1 0.080
-1 0 1 0.010
1 0 -1 0.100
0 1 0 0.260
0 -1 0 0.260
4 0 4 0.105
-4 0 -4 0.060


_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
#_diffrn_reflns_av_R_equivalents   0.033

# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device       'Nonius KappaCCD'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ' φ and ω scans with CCD '
_diffrn_special_details          
;
CCD data collecting conditions-
phi and omega scans of width 2.0 deg at rate 240 sec/frame,
crystal-detector distance 28mm,
multiple scan sets so over 90 percent of data collected with 4-fold  
redundancy or more.
;

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      200
_diffrn_reflns_number            16445
_reflns_number_total             1323
_diffrn_reflns_av_R_equivalents  0.039
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1323 
# Theoretical number of reflections is about 2274 


_diffrn_reflns_theta_min         3.005
_diffrn_reflns_theta_max         30.028
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.028
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              0
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.95
_oxford_diffrn_Wilson_scale      0.30

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.19
_refine_diff_density_max         0.16


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns         1323
_refine_ls_number_restraints     0
_refine_ls_number_parameters     124
_oxford_refine_ls_R_factor_ref   0.0443
_refine_ls_wR_factor_ref         0.1023
_refine_ls_goodness_of_fit_ref   1.0447
_refine_ls_shift/su_max          0.0049559
_refine_ls_shift/su_mean         0.0004 # 0.4384871 


# The values computed from all data 
_oxford_reflns_number_all        1323
_refine_ls_R_factor_all          0.0443
_refine_ls_wR_factor_all         0.1023

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1191
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_gt          0.0996

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration unk


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    refxyz # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

_refine_special_details          
;
The space group is noncentrosymmetric but  
the anomolous dispersion terms are very small
for all elements in the structure, so the
absolute structure of the crystal can not be determined in this experiment.
Consequently Friedel-pair reflections have been averaged and
the Flack parameter has not been refined.


The H atoms were all observed in a difference map, 
but were introduced at geometrically determined positions. 
They were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined without restraints
and the displacement parameters were held fixed. 


The largest peaks in the final difference electron density map 
are located midway along C---C bonds.


;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.41818(19) 0.57171(18) 0.46967(13) 0.0379 1.0000 Uani . . . . . . .
C2 C 0.3603(2) 0.74981(18) 0.45576(16) 0.0475 1.0000 Uani . . . . . . .
C3 C 0.3018(2) 0.7665(2) 0.35693(17) 0.0528 1.0000 Uani . . . . . . .
C4 C 0.3171(2) 0.6002(2) 0.30305(13) 0.0475 1.0000 Uani . . . . . . .
C5 C 0.4815(2) 0.5310(2) 0.35663(15) 0.0448 1.0000 Uani . . . . . . .
N6 N 0.3224(2) 0.16419(17) 0.52673(17) 0.0622 1.0000 Uani . . . . . . .
C7 C 0.2849(2) 0.29612(17) 0.50276(14) 0.0412 1.0000 Uani . . . . . . .
C8 C 0.24676(17) 0.46843(14) 0.47346(10) 0.0300 1.0000 Uani . . . . . . .
C9 C 0.17394(18) 0.48908(19) 0.35688(11) 0.0359 1.0000 Uani . . . . . . .
C10 C 0.1514(2) 0.3309(3) 0.30082(15) 0.0524 1.0000 Uani . . . . . . .
N11 N 0.1345(3) 0.2097(3) 0.25531(19) 0.0858 1.0000 Uani . . . . . . .
H11 H 0.500(2) 0.554(2) 0.5312(16) 0.0463 1.0000 Uiso . . . . . . .
H21 H 0.352(3) 0.836(2) 0.5148(17) 0.0575 1.0000 Uiso . . . . . . .
H31 H 0.244(3) 0.856(3) 0.3268(19) 0.0633 1.0000 Uiso . . . . . . .
H41 H 0.309(3) 0.596(3) 0.2279(18) 0.0583 1.0000 Uiso . . . . . . .
H52 H 0.592(3) 0.596(3) 0.3332(17) 0.0548 1.0000 Uiso . . . . . . .
H51 H 0.503(3) 0.409(3) 0.3424(16) 0.0516 1.0000 Uiso . . . . . . .
H81 H 0.165(2) 0.5077(19) 0.5265(14) 0.0375 1.0000 Uiso . . . . . . .
H91 H 0.061(3) 0.542(2) 0.3570(15) 0.0437 1.0000 Uiso . . . . . . .

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 0.0331(6) 0.0338(6) 0.0467(7) -0.0036(6) -0.0057(6) -0.0031(5)
C2 0.0437(8) 0.0300(6) 0.0688(10) -0.0042(7) 0.0036(8) -0.0047(6)
C3 0.0513(9) 0.0377(7) 0.0693(11) 0.0186(8) 0.0113(9) 0.0036(7)
C4 0.0505(9) 0.0562(9) 0.0358(7) 0.0099(7) 0.0077(7) 0.0059(8)
C5 0.0343(7) 0.0452(8) 0.0551(9) -0.0006(7) 0.0124(7) -0.0002(7)
N6 0.0556(9) 0.0390(7) 0.0921(12) 0.0165(8) -0.0027(9) 0.0021(7)
C7 0.0372(7) 0.0327(6) 0.0536(8) 0.0048(6) -0.0019(6) 0.0000(6)
C8 0.0305(5) 0.0273(6) 0.0324(6) -0.0014(5) -0.0013(5) 0.0015(5)
C9 0.0310(6) 0.0425(7) 0.0341(6) -0.0051(6) -0.0049(5) 0.0049(6)
C10 0.0360(8) 0.0676(11) 0.0535(9) -0.0252(9) -0.0104(7) 0.0043(8)
N11 0.0521(10) 0.1020(15) 0.1032(15) -0.0678(13) -0.0156(10) 0.0030(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.08(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.514(2) yes
C1 . C5 . 1.531(2) yes
C1 . C8 . 1.5631(19) yes
C1 . H11 . 1.01(2) no
C2 . C3 . 1.322(3) yes
C2 . H21 . 1.02(2) no
C3 . C4 . 1.506(3) yes
C3 . H31 . 0.93(2) no
C4 . C5 . 1.538(2) yes
C4 . C9 . 1.573(2) yes
C4 . H41 . 0.94(2) no
C5 . H52 . 1.04(2) no
C5 . H51 . 1.02(2) no
N6 . C7 . 1.143(2) yes
C7 . C8 . 1.4671(18) yes
C8 . C9 . 1.5708(19) yes
C8 . H81 . 0.966(18) no
C9 . C10 . 1.466(2) yes
C9 . H91 . 0.97(2) no
C10 . N11 . 1.138(3) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C5 . 101.05(14) yes
C2 . C1 . C8 . 105.04(12) yes
C5 . C1 . C8 . 100.55(12) yes
C2 . C1 . H11 . 113.9(11) no
C5 . C1 . H11 . 118.4(11) no
C8 . C1 . H11 . 115.8(11) no
C1 . C2 . C3 . 107.74(15) yes
C1 . C2 . H21 . 125.9(11) no
C3 . C2 . H21 . 125.8(12) no
C2 . C3 . C4 . 107.48(14) yes
C2 . C3 . H31 . 128.4(14) no
C4 . C3 . H31 . 123.3(14) no
C3 . C4 . C5 . 101.14(15) yes
C3 . C4 . C9 . 105.13(13) yes
C5 . C4 . C9 . 100.67(12) yes
C3 . C4 . H41 . 118.3(13) no
C5 . C4 . H41 . 118.5(14) no
C9 . C4 . H41 . 110.9(14) no
C4 . C5 . C1 . 93.53(12) yes
C4 . C5 . H52 . 111.7(12) no
C1 . C5 . H52 . 114.4(12) no
C4 . C5 . H51 . 114.1(11) no
C1 . C5 . H51 . 114.9(12) no
H52 . C5 . H51 . 107.8(17) no
N6 . C7 . C8 . 176.75(17) yes
C1 . C8 . C7 . 110.06(11) yes
C1 . C8 . C9 . 102.57(11) yes
C7 . C8 . C9 . 113.81(12) yes
C1 . C8 . H81 . 113.2(10) no
C7 . C8 . H81 . 105.6(10) no
C9 . C8 . H81 . 111.7(11) no
C8 . C9 . C4 . 101.92(11) yes
C8 . C9 . C10 . 113.19(13) yes
C4 . C9 . C10 . 112.00(14) yes
C8 . C9 . H91 . 111.5(12) no
C4 . C9 . H91 . 112.6(12) no
C10 . C9 . H91 . 105.8(12) no
C9 . C10 . N11 . 178.6(2) yes


#------------------------------------------------------------------------------
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
N6 C9 3.316(2) . 2_556 no
N6 C10 3.330(2) . 2_556 no
N6 C5 3.393(2) . 2_456 no
N6 C8 3.443(2) . 2_556 no
N6 C2 3.470(2) . 1_545 no
N6 C7 3.600(2) . 2_556 no
N11 C9 3.285(3) . 3_545 no
N11 C5 3.578(3) . 3_645 no
#------------------------------------------------------------------------------
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 C2 C3 C4 . . . . 0.7(2) no
C1 C5 C4 C3 . . . . 49.1(1) no
C1 C5 C4 C9 . . . . -58.8(1) no
C1 C8 C9 C4 . . . . 0.7(1) no
C1 C8 C9 C10 . . . . 121.1(1) no
C2 C1 C5 C4 . . . . -48.5(1) no
C2 C1 C8 C7 . . . . -171.6(1) no
C2 C1 C8 C9 . . . . 66.9(1) no
C2 C3 C4 C5 . . . . -33.2(2) no
C2 C3 C4 C9 . . . . 71.2(2) no
C3 C2 C1 C5 . . . . 32.3(2) no
C3 C2 C1 C8 . . . . -71.9(2) no
C3 C4 C9 C8 . . . . -68.5(1) no
C3 C4 C9 C10 . . . . 170.3(1) no
C4 C5 C1 C8 . . . . 59.3(1) no
C4 C9 C8 C7 . . . . -118.2(1) no
C5 C1 C8 C7 . . . . 83.8(1) no
C5 C1 C8 C9 . . . . -37.6(1) no
C5 C4 C9 C8 . . . . 36.3(1) no
C5 C4 C9 C10 . . . . -85.0(2) no
C7 C8 C9 C10 . . . . 2.3(2) no
