# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'David Millar'
_publ_contact_author_email       D.I.A.MILLAR@SMS.ED.AC.UK

_publ_section_title              
;
Putting the squeeze on energetic materials - structural
characterisation of a high-pressure phase of CL-20
;
loop_
_publ_author_name
'David Millar'
'Adam Cumming'
'Annette K. Kleppe'
'William G Marshall'
'Helen E Maynard-Casely'
;
C.R.Pulham
;

# Attachment '11.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 765864'
#TrackingRef '11.cif'

_exptl_special_details           
;
The crystal was
placed in the cold stream of an Oxford
Cryosystems open-flow nitrogen cryostat (Cosier &
Glazer, 1986) with a nominal stability of 0.1K.

Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107.
;
_refine_special_details          Restraints
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a                   12.579(2)
_cell_length_b                   7.7219(19)
_cell_length_c                   14.1260(15)
_cell_angle_alpha                90
_cell_angle_beta                 111.218(10)
_cell_angle_gamma                90
_cell_volume                     1279.1(4)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C6 H6 N12 O12
# Dc = 2.28 Fooo = 888.00 Mu = 2.18 M = 438.19
# Found Formula = C6 H6 N12 O12
# Dc = 2.28 FOOO = 888.00 Mu = 2.18 M = 438.19

_chemical_formula_sum            'C6 H6 N12 O12'
_chemical_formula_moiety         'C6 H6 N12 O12'
_chemical_compound_source        ?
_chemical_formula_weight         438.19

_cell_measurement_reflns_used    676
_cell_measurement_theta_min      3.094
_cell_measurement_theta_max      22.250
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.100

_exptl_crystal_density_diffrn    2.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000             888
_exptl_absorpt_coefficient_mu    0.218

# Sheldrick geometric approximatio 0.99 0.99
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device       'Bruker Kappa Apex2'
_diffrn_measurement_device_type  Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w/2\q

# 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      293
_diffrn_reflns_number            5107
_reflns_number_total             935
_diffrn_reflns_av_R_equivalents  0.128
# Number of reflections without Friedels Law is 0
# Number of reflections with Friedels Law is 935
# Theoretical number of reflections is about 3607

_diffrn_reflns_theta_min         3.094
_diffrn_reflns_theta_max         23.345
_diffrn_measured_fraction_theta_max 0.503

_diffrn_reflns_theta_full        17.508
_diffrn_measured_fraction_theta_full 0.636

_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -13
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   1.07
_oxford_diffrn_Wilson_scale      53.98

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

_refine_diff_density_min         -0.54
_refine_diff_density_max         0.48

# 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>2.0\s(I)
_refine_ls_number_reflns         515
_refine_ls_number_restraints     18
_refine_ls_number_parameters     121
_oxford_refine_ls_R_factor_ref   0.0877
_refine_ls_wR_factor_ref         0.0885
_refine_ls_goodness_of_fit_ref   1.1244
_refine_ls_shift/su_max          0.0000906
_refine_ls_shift/su_mean         2.5068915

# The values computed from all data
_oxford_reflns_number_all        929
_refine_ls_R_factor_all          0.1673
_refine_ls_wR_factor_all         0.1665

# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression     I>2.0\s(I)
_reflns_number_gt                515
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_gt          0.0885

# 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 F
_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.17 0.787 0.789
;
# 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. <i>Apex2</i>,
Version 2 User Manual, M86-E01078, Madison, WI.

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994).
Acta Cryst, A50, 411-437.

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
C1 C 0.6366(12) 0.111(3) 0.3579(10) 0.022(3) 1.0000 Uiso . . . . . . .
H1 H 0.7094 0.0776 0.4095 0.0261 1.0000 Uiso R . . . . . .
N1 N 0.5436(9) 0.0006(18) 0.3578(7) 0.016(3) 1.0000 Uiso D . . . . . .
N2 N 0.5623(8) -0.101(2) 0.4451(7) 0.027(3) 1.0000 Uiso D . . . . . .
O1 O 0.4769(8) -0.1568(18) 0.4542(6) 0.031(3) 1.0000 Uiso D . . . . . .
O2 O 0.6598(8) -0.119(2) 0.5015(7) 0.038(3) 1.0000 Uiso D . . . . . .
C2 C 0.4374(11) 0.102(3) 0.3153(9) 0.014(3) 1.0000 Uiso . . . . . . .
H2 H 0.3879 0.0769 0.3553 0.0151 1.0000 Uiso R . . . . . .
N3 N 0.3811(9) 0.0597(17) 0.2105(7) 0.020(3) 1.0000 Uiso D . . . . . .
N4 N 0.3126(9) -0.0885(17) 0.1907(7) 0.027(3) 1.0000 Uiso D . . . . . .
O3 O 0.3084(9) -0.1672(19) 0.1161(7) 0.040(3) 1.0000 Uiso D . . . . . .
O4 O 0.2664(8) -0.121(2) 0.2496(7) 0.039(3) 1.0000 Uiso D . . . . . .
C3 C 0.4472(11) 0.096(3) 0.1491(10) 0.018(3) 1.0000 Uiso . . . . . . .
H3 H 0.4010 0.0645 0.0786 0.0202 1.0000 Uiso R . . . . . .
N5 N 0.5517(9) -0.014(2) 0.1830(8) 0.022(3) 1.0000 Uiso D . . . . . .
N6 N 0.5767(8) -0.113(2) 0.1103(7) 0.029(3) 1.0000 Uiso D . . . . . .
O5 O 0.4973(7) -0.1568(18) 0.0356(6) 0.023(2) 1.0000 Uiso D . . . . . .
O6 O 0.6757(8) -0.1533(19) 0.1334(7) 0.039(3) 1.0000 Uiso D . . . . . .
C4 C 0.6441(12) 0.103(3) 0.2451(9) 0.023(4) 1.0000 Uiso . . . . . . .
H4 H 0.7192 0.0627 0.2492 0.0342 1.0000 Uiso R . . . . . .
N7 N 0.6132(8) 0.268(2) 0.1957(7) 0.018(3) 1.0000 Uiso D . . . . . .
N8 N 0.6673(9) 0.3124(17) 0.1281(8) 0.027(3) 1.0000 Uiso D . . . . . .
O7 O 0.7587(8) 0.2438(18) 0.1447(7) 0.032(3) 1.0000 Uiso D . . . . . .
O8 O 0.6268(8) 0.4298(17) 0.0705(7) 0.035(3) 1.0000 Uiso D . . . . . .
C5 C 0.4879(11) 0.277(3) 0.1576(10) 0.020(3) 1.0000 Uiso . . . . . . .
H5 H 0.4601 0.3350 0.0914 0.0264 1.0000 Uiso R . . . . . .
N9 N 0.4474(9) 0.370(2) 0.2282(7) 0.018(3) 1.0000 Uiso D . . . . . .
N10 N 0.4676(10) 0.550(2) 0.2329(9) 0.040(4) 1.0000 Uiso D . . . . . .
O9 O 0.4492(10) 0.630(2) 0.2986(8) 0.052(4) 1.0000 Uiso D . . . . . .
O10 O 0.5018(11) 0.608(2) 0.1694(10) 0.070(4) 1.0000 Uiso D . . . . . .
C6 C 0.4779(10) 0.294(3) 0.3283(9) 0.016(3) 1.0000 Uiso . . . . . . .
H6 H 0.4452 0.3631 0.3700 0.0202 1.0000 Uiso R . . . . . .
N11 N 0.6032(9) 0.287(2) 0.3748(7) 0.020(3) 1.0000 Uiso D . . . . . .
N12 N 0.6520(10) 0.3461(17) 0.4763(7) 0.033(4) 1.0000 Uiso D . . . . . .
O11 O 0.6085(9) 0.4750(18) 0.4938(8) 0.043(3) 1.0000 Uiso D . . . . . .
O12 O 0.7347(8) 0.270(2) 0.5306(7) 0.038(3) 1.0000 Uiso D . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1689(17)
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
O8 . N8 . 1.202(9) yes
N8 . O7 . 1.209(8) yes
N8 . N7 . 1.402(8) yes
N7 . C4 . 1.43(3) yes
N7 . C5 . 1.470(14) yes
C4 . N5 . 1.48(2) yes
C4 . C1 . 1.631(16) yes
C4 . H4 . 0.976 no
N5 . N6 . 1.404(9) yes
N5 . C3 . 1.49(2) yes
N6 . O5 . 1.209(8) yes
N6 . O6 . 1.208(8) yes
C3 . C5 . 1.48(3) yes
C3 . N3 . 1.429(15) yes
C3 . H3 . 0.984 no
C5 . N9 . 1.463(18) yes
C5 . H5 . 0.982 no
N9 . N10 . 1.414(9) yes
N9 . C6 . 1.447(17) yes
N10 . O9 . 1.204(9) yes
N10 . O10 . 1.213(9) yes
C6 . N11 . 1.473(16) yes
C6 . C2 . 1.56(2) yes
C6 . H6 . 0.989 no
N11 . C1 . 1.47(2) yes
N11 . N12 . 1.415(9) yes
C1 . N1 . 1.45(2) yes
C1 . H1 . 0.975 no
N1 . C2 . 1.476(18) yes
N1 . N2 . 1.408(9) yes
C2 . N3 . 1.429(16) yes
C2 . H2 . 0.999 no
N3 . N4 . 1.398(9) yes
N4 . O3 . 1.201(8) yes
N4 . O4 . 1.202(8) yes
N2 . O1 . 1.206(8) yes
N2 . O2 . 1.205(8) yes
N12 . O12 . 1.199(8) yes
N12 . O11 . 1.204(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
O8 . N8 . O7 . 127.0(10) yes
O8 . N8 . N7 . 117.1(9) yes
O7 . N8 . N7 . 115.0(10) yes
N8 . N7 . C4 . 115.9(11) yes
N8 . N7 . C5 . 117.3(9) yes
C4 . N7 . C5 . 106.6(12) yes
N7 . C4 . N5 . 103.7(11) yes
N7 . C4 . C1 . 110.0(15) yes
N5 . C4 . C1 . 106.8(12) yes
N7 . C4 . H4 . 113.4 no
N5 . C4 . H4 . 112.0 no
C1 . C4 . H4 . 110.6 no
C4 . N5 . N6 . 115.5(10) yes
C4 . N5 . C3 . 104.7(15) yes
N6 . N5 . C3 . 118.7(10) yes
N5 . N6 . O5 . 117.2(10) yes
N5 . N6 . O6 . 115.1(10) yes
O5 . N6 . O6 . 127.6(11) yes
N5 . C3 . C5 . 105.8(12) yes
N5 . C3 . N3 . 109.5(12) yes
C5 . C3 . N3 . 113.3(13) yes
N5 . C3 . H3 . 108.4 no
C5 . C3 . H3 . 111.9 no
N3 . C3 . H3 . 107.8 no
C3 . C5 . N7 . 106.2(15) yes
C3 . C5 . N9 . 108.9(12) yes
N7 . C5 . N9 . 111.4(11) yes
C3 . C5 . H5 . 111.3 no
N7 . C5 . H5 . 109.6 no
N9 . C5 . H5 . 109.4 no
C5 . N9 . N10 . 114.5(12) yes
C5 . N9 . C6 . 115.7(14) yes
N10 . N9 . C6 . 111.9(12) yes
N9 . N10 . O9 . 117.3(12) yes
N9 . N10 . O10 . 115.9(14) yes
O9 . N10 . O10 . 126.8(16) yes
N9 . C6 . N11 . 108.2(9) yes
N9 . C6 . C2 . 108.0(12) yes
N11 . C6 . C2 . 105.7(13) yes
N9 . C6 . H6 . 110.1 no
N11 . C6 . H6 . 111.2 no
C2 . C6 . H6 . 113.2 no
C6 . N11 . C1 . 106.4(12) yes
C6 . N11 . N12 . 116.3(10) yes
C1 . N11 . N12 . 114.7(11) yes
N11 . C1 . C4 . 108.2(14) yes
N11 . C1 . N1 . 105.5(10) yes
C4 . C1 . N1 . 108.1(12) yes
N11 . C1 . H1 . 111.5 no
C4 . C1 . H1 . 110.5 no
N1 . C1 . H1 . 112.8 no
C1 . N1 . C2 . 107.5(13) yes
C1 . N1 . N2 . 116.6(11) yes
C2 . N1 . N2 . 119.5(8) yes
C6 . C2 . N1 . 104.4(11) yes
C6 . C2 . N3 . 111.0(12) yes
N1 . C2 . N3 . 109.6(12) yes
C6 . C2 . H2 . 111.3 no
N1 . C2 . H2 . 108.9 no
N3 . C2 . H2 . 111.4 no
C3 . N3 . C2 . 113.9(10) yes
C3 . N3 . N4 . 119.3(11) yes
C2 . N3 . N4 . 115.6(11) yes
N3 . N4 . O3 . 114.6(10) yes
N3 . N4 . O4 . 116.9(10) yes
O3 . N4 . O4 . 128.5(12) yes
N1 . N2 . O1 . 114.8(10) yes
N1 . N2 . O2 . 116.8(9) yes
O1 . N2 . O2 . 128.4(10) yes
N11 . N12 . O12 . 116.6(11) yes
N11 . N12 . O11 . 114.3(11) yes
O12 . N12 . O11 . 128.9(12) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H6 . O11 2_666 170 0.99 2.58 3.56(2) yes
C1 . H1 . O8 3_645 142 0.98 2.28 3.11(2) yes
C2 . H2 . O2 2_656 151 1.00 2.33 3.24(2) yes

_chemical_name_common            'Zeta CL-20 at 3.3 GPa'