# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

data_10098
_audit_creation_date             10-10-05
_audit_creation_method           CRYSTALS_ver_14.06

_oxford_structure_analysis_title 'mo_10098_0m in P4(2)/nnm'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_cell_length_a                   10.4576(10)
_cell_length_b                   10.4576(10)
_cell_length_c                   16.6823(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1824.4(3)

_symmetry_cell_setting           Tetragonal
_symmetry_space_group_name_H-M   'P 42/n n m '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-y+1/2,x,z+1/2
y+1/2,-x,-z+1/2
-x+1/2,-y+1/2,z
x+1/2,y+1/2,-z
y,-x+1/2,z+1/2
-y,x+1/2,-z+1/2
-x,y+1/2,z+1/2
x,-y+1/2,-z+1/2
y+1/2,x+1/2,z
-y+1/2,-x+1/2,-z
x+1/2,-y,z+1/2
-x+1/2,y,-z+1/2
-y,-x,z
y,x,-z

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'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 '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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Fe 0.3463 0.8444 11.7695 4.7611 7.3573 0.3072 3.5222 15.3535 2.3045 76.8805
1.0369 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C26 H24 B2 F8 Fe1 N20 
# Dc =      1.54 Fooo =    856.00 Mu =      5.07 M =    105.76
# Found Formula = C26 H24 B2 F8 Fe1 N20 
# Dc =      1.54 FOOO =    856.00 Mu =      5.07 M =    105.76

_chemical_formula_sum            'C26 H24 B2 F8 Fe1 N20'
_chemical_formula_moiety         'C26 H24 B2 F8 Fe1 N20'
_chemical_compound_source        ?
_chemical_formula_weight         846.06


_cell_measurement_reflns_used    1525
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_temperature    150

_exptl_crystal_description       cubic
_exptl_crystal_colour            bronze
_exptl_crystal_size_min          0.079
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_max          0.118

_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    0.507

# Sheldrick geometric approximatio 0.95 0.96 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.96
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            5885
_reflns_number_total             886
_diffrn_reflns_av_R_equivalents  0.040
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 886 
# Theoretical number of reflections is about 1616 


_diffrn_reflns_theta_min         2.299
_diffrn_reflns_theta_max         25.054
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        25.054
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              0
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              12
_reflns_limit_l_min              0
_reflns_limit_l_max              19

_oxford_diffrn_Wilson_B_factor   0.78
_oxford_diffrn_Wilson_scale      156.29

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

_refine_diff_density_min         -2.31
_refine_diff_density_max         3.00


# 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         886
_refine_ls_number_restraints     47
_refine_ls_number_parameters     73
_oxford_refine_ls_R_factor_ref   0.1253
_refine_ls_wR_factor_ref         0.4223
_refine_ls_goodness_of_fit_ref   0.9965
_refine_ls_shift/su_max          0.0005043
_refine_ls_shift/su_mean         0.0000367


# The values computed from all data 
_oxford_reflns_number_all        886
_refine_ls_R_factor_all          0.1253
_refine_ls_wR_factor_all         0.4223

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                726
_refine_ls_R_factor_gt           0.1142
_refine_ls_wR_factor_gt          0.3845

# 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    none # 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) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references         
; 
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., 
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. 
 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Bruker Analytical X-ray Systems, Inc., 2006. Apex2, 
Version 2 User Manual, M86-E01078, Madison, WI. 
 
De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
;

# 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
Fe1 Fe 0.2500 0.7500 0.7500 0.0125 1.0000 Uani S T . . . . .
F1 F 0.7355 0.6479 0.7066 0.1533 0.5000 Uiso . . . . . . .
F2 F 0.6475 0.7665 0.7990 0.1316 0.5000 Uiso . . . . . . .
N1 N 0.2500 0.7500 0.6361(7) 0.0179 1.0000 Uani S T . . . . .
N2 N 0.4919(5) 0.5081(5) 0.6306(5) 0.0296 1.0000 Uani S T . . . . .
N3 N 0.5520(5) 0.4480(5) 0.6851(5) 0.0284 1.0000 Uani S TU . . . . .
N4 N 0.3801(5) 0.6199(5) 0.7319(4) 0.0170 1.0000 Uani S T . . . . .
N5 N 0.4415(5) 0.5585(5) 0.7869(4) 0.0237 1.0000 Uani S TU . . . . .
C1 C 0.250000(7) 0.750000(7) 0.4749(8) 0.0212 1.0000 Uani S TU . . . . .
C2 C 0.3326(6) 0.6674(6) 0.5128(5) 0.0205 1.0000 Uani S TU . . . . .
C3 C 0.3300(6) 0.6700(6) 0.5983(5) 0.0184 1.0000 Uani S TU . . . . .
C4 C 0.4052(6) 0.5948(6) 0.6519(4) 0.0191 1.0000 Uani S TU . . . . .
C5 C 0.5258(7) 0.4742(7) 0.7632(6) 0.0262 1.0000 Uani S TU . . . . .
C6 C 0.5989(7) 0.4011(7) 0.8248(6) 0.0282 1.0000 Uani S TU . . . . .
C7 C 0.8046(6) 0.6954(6) 0.500000(10) 0.129(8) 1.0000 Uiso DS . . . . . .
B1 B 0.7500 0.7500 0.7500 0.0230 1.0000 Uiso . . . . . . .
H11 H 0.2500 0.7500 0.4179 0.0242 1.0000 Uiso RS . . . . . .
H21 H 0.3885 0.6115 0.4847 0.0211 1.0000 Uiso RS . . . . . .
H61 H 0.5693 0.4307 0.8753 0.0394 1.0000 Uiso RS . . . . . .
H62 H 0.5832 0.3119 0.8203 0.0394 1.0000 Uiso R . . . . . .
N6 N 0.8828 0.6172 0.5000 0.0500 0.5000 Uiso D . . 1 2 . .
H71 H 0.8280 0.6720 0.4469 0.0919 0.2500 Uiso R . . 1 1 . .
H72 H 0.7726 0.6225 0.5274 0.0919 0.2500 Uiso R . . 1 1 . .
H73 H 0.8775 0.7274 0.5274 0.0919 0.2500 Uiso R . . 1 1 . .
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
Fe1 0.0135(12) 0.0135(12) 0.0103(15) 0.0000 0.0000 0.0000
N1 0.020(4) 0.020(4) 0.014(5) 0.0000 0.0000 -0.005(4)
N2 0.024(3) 0.024(3) 0.041(5) -0.006(3) 0.006(3) 0.001(3)
N3 0.024(2) 0.024(2) 0.036(3) 0.001(2) -0.001(2) 0.003(3)
N4 0.017(2) 0.017(2) 0.017(4) -0.004(2) 0.004(2) -0.004(3)
N5 0.020(2) 0.020(2) 0.031(3) 0.0056(19) -0.0056(19) 0.000(2)
C1 0.026(3) 0.026(3) 0.012(4) 0.0000 0.0000 -0.008(3)
C2 0.025(2) 0.025(2) 0.011(3) -0.0023(14) 0.0023(14) -0.003(2)
C3 0.023(2) 0.023(2) 0.010(3) -0.0027(16) 0.0027(16) -0.002(2)
C4 0.022(2) 0.022(2) 0.013(3) -0.0030(18) 0.0030(18) 0.001(3)
C5 0.0215(19) 0.0215(19) 0.036(3) 0.0041(17) -0.0041(17) 0.002(2)
C6 0.022(2) 0.022(2) 0.040(4) 0.008(2) -0.008(2) 0.004(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.0991(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
Fe1 . N4 5_565 1.947(7) yes
Fe1 . N4 14_556 1.947(7) yes
Fe1 . N4 8_656 1.947(7) yes
Fe1 . N1 4_466 1.900(11) yes
Fe1 . N1 . 1.900(11) yes
Fe1 . N4 . 1.947(7) yes
F1 . F1 14_656 1.47881(14) yes
F1 . F2 10_566 1.28743(9) yes
F1 . F2 14_656 1.74453(12) yes
F1 . B1 . 1.29844(9) yes
F2 . F2 10_566 1.67064(16) yes
F2 . B1 . 1.35924(10) yes
N1 . C3 11_455 1.340(10) yes
N1 . C3 . 1.340(10) yes
N2 . N3 . 1.273(12) yes
N2 . C4 . 1.331(12) yes
N3 . C5 . 1.358(13) yes
N4 . N5 . 1.291(10) yes
N4 . C4 . 1.385(10) yes
N5 . C5 . 1.308(12) yes
C1 . C2 11_455 1.376(10) yes
C1 . C2 . 1.376(10) yes
C1 . H11 . 0.950 no
C2 . C3 . 1.428(11) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.427(12) yes
C5 . C6 . 1.492(13) yes
C6 . H62 15_665 0.950 no
C6 . H61 . 0.950 no
C6 . H62 . 0.950 no
C7 . C7 5_665 1.615(18) yes
C7 . H73 12_666 0.950 no
C7 . H71 12_666 0.950 no
C7 . H72 12_666 0.950 no
C7 . H71 . 0.950 no
C7 . H72 . 0.950 no
C7 . H73 . 0.950 no
C7 . N6 . 1.157(9) 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
N4 5_565 Fe1 . N4 14_556 91.38(6) yes
N4 5_565 Fe1 . N4 8_656 91.38(6) yes
N4 14_556 Fe1 . N4 8_656 162.2(4) yes
N4 5_565 Fe1 . N1 4_466 98.9(2) yes
N4 14_556 Fe1 . N1 4_466 81.1(2) yes
N4 8_656 Fe1 . N1 4_466 81.1(2) yes
N4 5_565 Fe1 . N1 . 81.1(2) yes
N4 14_556 Fe1 . N1 . 98.9(2) yes
N4 8_656 Fe1 . N1 . 98.9(2) yes
N1 4_466 Fe1 . N1 . 179.994 yes
N4 5_565 Fe1 . N4 . 162.2(4) yes
N4 14_556 Fe1 . N4 . 91.38(6) yes
N4 8_656 Fe1 . N4 . 91.38(6) yes
N1 4_466 Fe1 . N4 . 98.9(2) yes
N1 . Fe1 . N4 . 81.1(2) yes
F1 14_656 F1 . F2 10_566 102.551(6) yes
F1 14_656 F1 . F2 14_656 84.784(8) yes
F2 10_566 F1 . F2 14_656 90.225(8) yes
F1 14_656 F1 . B1 . 55.288 yes
F2 10_566 F1 . B1 . 63.421(6) yes
F2 14_656 F1 . B1 . 50.497(4) yes
F1 10_566 F2 . F2 10_566 94.169(5) yes
F1 10_566 F2 . F1 14_656 89.330(8) yes
F2 10_566 F2 . F1 14_656 78.495(6) yes
F1 10_566 F2 . B1 . 58.684(6) yes
F2 10_566 F2 . B1 . 52.081 yes
F1 14_656 F2 . B1 . 47.484(4) yes
C3 11_455 N1 . Fe1 . 118.0(6) yes
C3 11_455 N1 . C3 . 124.0(11) yes
Fe1 . N1 . C3 . 118.0(6) yes
N3 . N2 . C4 . 118.8(8) yes
N2 . N3 . C5 . 119.1(8) yes
Fe1 . N4 . N5 . 125.8(6) yes
Fe1 . N4 . C4 . 114.5(6) yes
N5 . N4 . C4 . 119.7(8) yes
N4 . N5 . C5 . 117.2(8) yes
C2 11_455 C1 . C2 . 125.2(12) yes
C2 11_455 C1 . H11 . 117.4 no
C2 . C1 . H11 . 117.4 no
C1 . C2 . C3 . 115.8(9) yes
C1 . C2 . H21 . 123.0 no
C3 . C2 . H21 . 121.1 no
C2 . C3 . N1 . 119.5(9) yes
C2 . C3 . C4 . 127.3(8) yes
N1 . C3 . C4 . 113.2(8) yes
C3 . C4 . N4 . 113.3(8) yes
C3 . C4 . N2 . 125.6(8) yes
N4 . C4 . N2 . 121.1(8) yes
N3 . C5 . N5 . 124.2(9) yes
N3 . C5 . C6 . 117.0(9) yes
N5 . C5 . C6 . 118.8(8) yes
C5 . C6 . H62 15_665 111.1 no
C5 . C6 . H61 . 106.2 no
H62 15_665 C6 . H61 . 109.5 no
C5 . C6 . H62 . 111.1 no
H62 15_665 C6 . H62 . 109.5 no
H61 . C6 . H62 . 109.5 no
C7 5_665 C7 . H73 12_666 108.5 no
C7 5_665 C7 . H71 12_666 111.3 no
H73 12_666 C7 . H71 12_666 109.5 no
C7 5_665 C7 . H72 12_666 108.5 no
H73 12_666 C7 . H72 12_666 109.5 no
H71 12_666 C7 . H72 12_666 109.5 no
C7 5_665 C7 . H71 . 111.3 no
H73 12_666 C7 . H71 . 55.6 no
H71 12_666 C7 . H71 . 137.4 no
H72 12_666 C7 . H71 . 55.6 no
C7 5_665 C7 . H72 . 108.5 no
H73 12_666 C7 . H72 . 57.6 no
H71 12_666 C7 . H72 . 55.6 no
H72 12_666 C7 . H72 . 142.9 no
H71 . C7 . H72 . 109.5 no
C7 5_665 C7 . H73 . 108.5 no
H73 12_666 C7 . H73 . 142.9 no
H71 12_666 C7 . H73 . 55.6 no
H72 12_666 C7 . H73 . 57.6 no
H71 . C7 . H73 . 109.5 no
H72 . C7 . H73 . 109.5 no
F2 . B1 . F2 14_656 165.394 yes
F2 . B1 . F2 10_566 75.838(8) yes
F2 14_656 B1 . F2 10_566 106.080(8) yes
F2 . B1 . F2 5_665 106.080(8) yes
F2 14_656 B1 . F2 5_665 75.838(8) yes
F2 10_566 B1 . F2 5_665 165.394 yes
F2 . B1 . F1 14_656 82.019(6) yes
F2 14_656 B1 . F1 14_656 110.354(6) yes
F2 10_566 B1 . F1 14_656 108.814(4) yes
F2 5_665 B1 . F1 14_656 57.895(4) yes
F2 . B1 . F1 10_566 57.895(4) yes
F2 14_656 B1 . F1 10_566 108.814(4) yes
F2 10_566 B1 . F1 10_566 110.354(6) yes
F2 5_665 B1 . F1 10_566 82.019(6) yes
F1 14_656 B1 . F1 10_566 112.243(7) yes
F2 . B1 . F1 5_665 108.814(4) yes
F2 14_656 B1 . F1 5_665 57.895(4) yes
F2 10_566 B1 . F1 5_665 82.019(6) yes
F2 5_665 B1 . F1 5_665 110.354(6) yes
F1 14_656 B1 . F1 5_665 166.631 yes
F2 . B1 . F1 . 110.354(6) yes
F2 14_656 B1 . F1 . 82.019(6) yes
F2 10_566 B1 . F1 . 57.895(4) yes
F2 5_665 B1 . F1 . 108.814(4) yes
F1 14_656 B1 . F1 . 69.424(7) yes
F1 10_566 B1 . F1 5_665 69.424(7) yes
F1 10_566 B1 . F1 . 166.631 yes
F1 5_665 B1 . F1 . 112.243(7) yes

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
N4 Fe1 N1 C3 0.0(3) . . . . no
N1 Fe1 N4 N5 -180.0(5) . . . . no
N1 Fe1 N4 C4 0.0(4) . . . . no
Fe1 N1 C3 C2 180.0(4) . . . . no
Fe1 N1 C3 C4 0.0(6) . . . . no
C4 N2 N3 C5 0.0(9) . . . . no
N3 N2 C4 N4 0.0(9) . . . . no
N3 N2 C4 C3 180.0(6) . . . . no
N2 N3 C5 N5 0.0(10) . . . . no
N2 N3 C5 C6 180.0(6) . . . . no
Fe1 N4 N5 C5 180.0(5) . . . . no
C4 N4 N5 C5 0.0(9) . . . . no
Fe1 N4 C4 N2 -180.0(4) . . . . no
Fe1 N4 C4 C3 0.0(7) . . . . no
N5 N4 C4 N2 0.0(9) . . . . no
N5 N4 C4 C3 180.0(5) . . . . no
N4 N5 C5 N3 0.0(10) . . . . no
N4 N5 C5 C6 180.0(6) . . . . no
C1 C2 C3 N1 0.0(8) . . . . no
C1 C2 C3 C4 180.0(5) . . . . no
N1 C3 C4 N2 180.0(5) . . . . no
N1 C3 C4 N4 0.0(7) . . . . no
C2 C3 C4 N2 0.0(11) . . . . no
C2 C3 C4 N4 -180.0(6) . . . . no
_database_code_depnum_ccdc_archive 'CCDC 955991'
data_10096
_audit_creation_date             10-09-30
_audit_creation_method           CRYSTALS_ver_14.06

_oxford_structure_analysis_title '10096 in P2(1)/m'
_chemical_name_systematic        ?
_chemical_melting_point          ?
_cell_length_a                   3.9077(4)
_cell_length_b                   26.893(2)
_cell_length_c                   5.4464(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.622(3)
_cell_angle_gamma                90
_cell_volume                     572.34(9)

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

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            2

# Given Formula = C11 H9 N9 
# Dc =      1.55 Fooo =    276.00 Mu =      1.08 M =    133.63
# Found Formula = C11 H9 N9 
# Dc =      1.55 FOOO =    276.00 Mu =      1.08 M =    133.63

_chemical_formula_sum            'C11 H9 N9'
_chemical_formula_moiety         'C11 H9 N9'
_chemical_compound_source        ?
_chemical_formula_weight         267.25


_cell_measurement_reflns_used    3751
_cell_measurement_theta_min      4
_cell_measurement_theta_max      34
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_min          0.070
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_max          0.329

_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.108

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            14413
_reflns_number_total             2472
_diffrn_reflns_av_R_equivalents  0.032
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2472 
# Theoretical number of reflections is about 5435 


_diffrn_reflns_theta_min         3.741
_diffrn_reflns_theta_max         36.027
_diffrn_measured_fraction_theta_max 0.894

_diffrn_reflns_theta_full        29.182
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              41
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.52
_refine_diff_density_max         0.53


# 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         2472
_refine_ls_number_restraints     0
_refine_ls_number_parameters     94
_oxford_refine_ls_R_factor_ref   0.0741
_refine_ls_wR_factor_ref         0.1814
_refine_ls_goodness_of_fit_ref   1.0848
_refine_ls_shift/su_max          0.0006562
_refine_ls_shift/su_mean         0.0000640


# The values computed from all data 
_oxford_reflns_number_all        2472
_refine_ls_R_factor_all          0.0741
_refine_ls_wR_factor_all         0.1814

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1851
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_gt          0.1534

# 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    none # 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) + ( 0.09P)² + 0.27P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references         
; 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Bruker Analytical X-ray Systems, Inc., 2006. Apex2, 
Version 2 User Manual, M86-E01078, Madison, WI. 
 
De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. 
 
Sheldrick, G. M. (2008). Acta Cryst A64, 112-122. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
;

# 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
N1 N 0.6837(4) 0.7500 0.1624(3) 0.0154 1.0000 Uani S T . . . . .
N2 N 0.5658(3) 0.61834(4) 0.2300(2) 0.0237 1.0000 Uani . . . . . . .
N3 N 0.6231(3) 0.57739(4) 0.1003(2) 0.0242 1.0000 Uani . . . . . . .
N4 N 0.9069(3) 0.66454(4) -0.0441(2) 0.0216 1.0000 Uani . . . . . . .
N5 N 0.9627(3) 0.62377(4) -0.1726(2) 0.0230 1.0000 Uani . . . . . . .
C1 C 0.3121(5) 0.7500 0.6006(3) 0.0184 1.0000 Uani S T . . . . .
C2 C 0.4060(3) 0.70575(5) 0.4898(2) 0.0175 1.0000 Uani . . . . . . .
C3 C 0.5904(3) 0.70777(4) 0.2722(2) 0.0153 1.0000 Uani . . . . . . .
C4 C 0.6892(3) 0.66129(4) 0.1447(2) 0.0163 1.0000 Uani . . . . . . .
C5 C 0.7990(3) 0.58194(5) -0.1068(2) 0.0194 1.0000 Uani . . . . . . .
C6 C 0.8374(4) 0.53805(5) -0.2691(3) 0.0283 1.0000 Uani . . . . . . .
H11 H 0.1856 0.7500 0.7490 0.0221 1.0000 Uiso . . . . . . .
H21 H 0.3456 0.6745 0.5611 0.0214 1.0000 Uiso . . . . . . .
H61 H 0.8550 0.5486 -0.4356 0.0347 1.0000 Uiso . . . . . . .
H62 H 0.6424 0.5169 -0.2546 0.0347 1.0000 Uiso . . . . . . .
H63 H 1.0371 0.5200 -0.2244 0.0347 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
N1 0.0169(6) 0.0132(6) 0.0162(6) 0.0000 0.0025(5) 0.0000
N2 0.0335(6) 0.0129(5) 0.0249(6) 0.0011(4) 0.0097(5) -0.0019(4)
N3 0.0326(6) 0.0134(5) 0.0269(6) 0.0003(4) 0.0096(5) -0.0015(4)
N4 0.0255(5) 0.0149(5) 0.0246(6) -0.0006(4) 0.0096(4) -0.0009(4)
N5 0.0287(6) 0.0154(5) 0.0251(5) -0.0014(4) 0.0085(4) -0.0006(4)
C1 0.0204(7) 0.0189(7) 0.0158(7) 0.0000 0.0017(6) 0.0000
C2 0.0193(5) 0.0166(5) 0.0167(5) 0.0013(4) 0.0031(4) -0.0007(4)
C3 0.0173(5) 0.0130(5) 0.0157(5) 0.0000(4) 0.0007(4) -0.0004(4)
C4 0.0187(5) 0.0138(5) 0.0166(5) 0.0013(4) 0.0022(4) -0.0007(4)
C5 0.0226(5) 0.0152(5) 0.0205(6) -0.0009(4) 0.0015(4) 0.0008(4)
C6 0.0359(7) 0.0187(6) 0.0303(7) -0.0070(5) 0.0065(6) -0.0012(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2963(7)
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
N1 . C3 4_565 1.3362(14) yes
N1 . C3 . 1.3362(14) yes
N2 . N3 . 1.3288(16) yes
N2 . C4 . 1.3369(15) yes
N3 . C5 . 1.3326(18) yes
N4 . N5 . 1.3202(15) yes
N4 . C4 . 1.3447(17) yes
N5 . C5 . 1.3446(17) yes
C1 . C2 4_565 1.3857(15) yes
C1 . C2 . 1.3857(15) yes
C1 . H11 . 0.952 no
C2 . C3 . 1.3947(17) yes
C2 . H21 . 0.956 no
C3 . C4 . 1.4830(17) yes
C5 . C6 . 1.4833(19) yes
C6 . H61 . 0.954 no
C6 . H62 . 0.954 no
C6 . H63 . 0.949 no
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
C3 4_565 N1 . C3 . 116.43(15) yes
N3 . N2 . C4 . 117.89(11) yes
N2 . N3 . C5 . 117.73(11) yes
N5 . N4 . C4 . 117.44(11) yes
N4 . N5 . C5 . 118.15(11) yes
C2 4_565 C1 . C2 . 118.39(16) yes
C2 4_565 C1 . H11 . 120.8 no
C2 . C1 . H11 . 120.8 no
C1 . C2 . C3 . 118.57(12) yes
C1 . C2 . H21 . 120.7 no
C3 . C2 . H21 . 120.8 no
C2 . C3 . N1 . 124.02(11) yes
C2 . C3 . C4 . 120.30(10) yes
N1 . C3 . C4 . 115.67(11) yes
C3 . C4 . N4 . 118.26(10) yes
C3 . C4 . N2 . 117.95(11) yes
N4 . C4 . N2 . 123.75(11) yes
N5 . C5 . N3 . 123.62(12) yes
N5 . C5 . C6 . 117.08(12) yes
N3 . C5 . C6 . 119.19(12) yes
C5 . C6 . H61 . 109.8 no
C5 . C6 . H62 . 109.8 no
H61 . C6 . H62 . 108.8 no
C5 . C6 . H63 . 110.1 no
H61 . C6 . H63 . 109.2 no
H62 . C6 . H63 . 109.2 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C3 C2 0.1(2) 4_565 . . . no
C3 N1 C3 C4 178.67(12) 4_565 . . . no
C4 N2 N3 C5 -0.1(2) . . . . no
N3 N2 C4 N4 -9.88(19) . . . . no
N3 N2 C4 C3 172.72(11) . . . . no
N2 N3 C5 N5 10.0(2) . . . . no
N2 N3 C5 C6 -173.88(12) . . . . no
C4 N4 N5 C5 0.06(17) . . . . no
N5 N4 C4 N2 9.88(18) . . . . no
N5 N4 C4 C3 -172.74(11) . . . . no
N4 N5 C5 N3 -10.02(19) . . . . no
N4 N5 C5 C6 173.79(12) . . . . no
C2 C1 C2 C3 -0.1(2) 4_565 . . . no
C1 C2 C3 N1 0.0(2) . . . . no
C1 C2 C3 C4 -178.52(13) . . . . no
N1 C3 C4 N2 -171.84(12) . . . . no
N1 C3 C4 N4 10.62(17) . . . . no
C2 C3 C4 N2 6.79(17) . . . . no
C2 C3 C4 N4 -170.75(11) . . . . no
_database_code_depnum_ccdc_archive 'CCDC 955992'
