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

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'MacGillivray, Len'
_publ_contact_author_email       len-macgillivray@uiowa.edu

_publ_section_title              
;
A solid-state trimerisation of a diene diacid affords a bicyclobutyl:
reactant structure from X-ray powder data and product separation and
structure determination via co-crystallisation
;
loop_
_publ_author_name
L.MacGillivray
M.Atkinson
I.Halasz
D.-K.Bucar
R.Dinnebier
;
S.V.S.Mariappan
;
A.Sokolov

# Attachment '1.cif'

data_1
_database_code_depnum_ccdc_archive 'CCDC 780278'

_chemical_formula_sum            'C8 H10 O4'
_chemical_formula_weight         170.166
_chemical_formula_moiety         'C8 H10 O4'
_symmetry_cell_setting           monoclinic
_cell_formula_units_Z            2
_diffrn_measurement_device_type  
;
Bruker D8 Advance in Debye-Scherrer geometry
;
_diffrn_ambient_temperature      293
_diffrn_radiation_type           'Cu K\a_1'
_diffrn_radiation_wavelength     1.54059
_exptl_crystal_density_diffrn    1.369
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          <0.01
_refine_ls_number_parameters     74
_pd_proc_ls_prof_R_factor        0.0282
_pd_proc_ls_prof_wR_factor       0.0376
_refine_ls_R_Fsqd_factor         0.0140
_refine_ls_goodness_of_fit_all   1.72
_cell_measurement_temperature    293
_exptl_crystal_description       'microcrystaline flake-like powder'
_exptl_crystal_colour            white
_refine_ls_structure_factor_coef Fsqd
_exptl_special_details           
;

;
_pd_proc_ls_profile_function     
;
Calculated from fundamental parameters
;

_cell_length_a                   3.898360(63)
_cell_length_b                   7.87939(11)
_cell_length_c                   13.51483(35)
_cell_angle_alpha                90
_cell_angle_beta                 95.9652(16)
_cell_angle_gamma                90
_cell_volume                     412.883(14)
_symmetry_space_group_name_H-M   P21/c
_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+1/2, z+1/2'
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
O1 O 4 0.44142(54) 0.90080(27) 0.39264(17) 1 7.80
C1 C 4 0.30365(39) 0.78823(36) 0.43855(18) 1 2.67
O2 O 4 0.28793(38) 0.81190(13) 0.53346(13) 1 6.13
C2 C 4 0.16025(60) 0.63123(30) 0.39784(15) 1 1.20
C3 C 4 0.01802(42) 0.50242(17) 0.44694(10) 1 3.34
C4 C 4 0.19820(60) 0.61876(27) 0.28346(23) 1 4.60
H1 H 4 0.2091(22) 0.4915(10) 0.26394(78) 1 6.91
H2 H 4 -0.0042(19) 0.6824(11) 0.24174(55) 1 6.91
H3 H 4 0.4154(20) 0.6795(11) 0.27027(58) 1 6.91
H4 H 4 -0.0696(22) 0.40036(94) 0.40366(49) 1 1.44
H1o H 4 0.3782(21) 0.90771(96) 0.55765(53) 1 7.36

_vrf_ATOM006_Muco                
;
PROBLEM: _atom_site_U_iso_or_equiv is missing
RESPONSE: Displacement parameters are reported as B_iso.
;
_vrf_GEOM001_Muco                
;
PROBLEM: _geom_bond_atom_site_label_1 is missing
RESPONSE: Bonds and angles not calculated.
;
_vrf_GEOM003_Muco                
;
PROBLEM: _geom_bond_distance is missing
RESPONSE: Bonds and angles not calculated.
;
_vrf_GEOM006_Muco                
;
PROBLEM: _geom_angle_atom_site_label_2 is missing
RESPONSE: Bonds and angles not calculated.
;
_vrf_GEOM007_Muco                
;
PROBLEM: _geom_angle_atom_site_label_3 is missing
RESPONSE: Bonds and angles not calculated.
;

_vrf_PLAT762_Muco                
;
PROBLEM: CIF Contains no X-Y-H or H-Y-H Angles
RESPONSE: Bonds and angles not calculated.
;

# Attachment '- 2-revised.cif'

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 780279'
#TrackingRef '- 2-revised.cif'

_audit_creation_date             2010-08-03T12:19:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
?
;
_chemical_formula_sum            'C50 H60 N6 O14'
_chemical_formula_moiety         'C24 H30 O12, 2(C10 H8 N2), 2(C3 H7 N O)'
_chemical_formula_weight         969.04

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

_cell_length_a                   8.1654(9)
_cell_length_b                   11.7147(13)
_cell_length_c                   13.1518(14)
_cell_angle_alpha                86.292(5)
_cell_angle_beta                 77.546(5)
_cell_angle_gamma                78.982(5)
_cell_volume                     1205.4(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.88
_cell_measurement_reflns_used    5687

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             514

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'HKL Scalepack (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_T_max  0.9922

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

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.019
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_number            8097
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.87
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_detector_area_resol_mean 9
_reflns_number_total             4184
_reflns_number_gt                3463
_reflns_threshold_expression     >2\s(I)

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

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo, Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'Rastop (Valadon, 2004)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_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^)+(0.0713P)^2^+0.4585P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     324
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.046
_refine_ls_wR_factor_ref         0.1273
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.5
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
# 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'
O O 0.0106 0.006 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2277(2) 1.05236(15) 0.82153(13) 0.0268(4) Uani 1 1 d . . .
C2 C 0.1166(2) 1.12583(14) 0.91028(13) 0.0232(4) Uani 1 1 d . . .
C3 C 0.00016(19) 1.06485(13) 1.00137(12) 0.0203(4) Uani 1 1 d . . .
C4 C -0.1625(2) 1.15173(14) 0.98036(12) 0.0218(4) Uani 1 1 d . . .
C5 C -0.0498(2) 1.19996(14) 0.88028(12) 0.0237(4) Uani 1 1 d . . .
C6 C -0.0548(2) 1.32759(15) 0.86404(13) 0.0283(4) Uani 1 1 d . . .
C7 C -0.0047(2) 1.38727(15) 0.77590(14) 0.0299(4) Uani 1 1 d . . .
C8 C 0.0611(3) 1.32752(17) 0.67495(14) 0.0342(4) Uani 1 1 d . . .
C9 C -0.2295(2) 1.24410(14) 1.06276(13) 0.0240(4) Uani 1 1 d . . .
C10 C 0.2224(2) 1.19837(16) 0.95228(14) 0.0302(4) Uani 1 1 d . . .
C11 C -0.3069(2) 1.10080(15) 0.95451(14) 0.0278(4) Uani 1 1 d . . .
C12 C -0.0084(3) 1.51602(17) 0.77452(16) 0.0420(5) Uani 1 1 d . . .
C13 C 0.2153(2) 0.75568(17) 0.62478(14) 0.0339(4) Uani 1 1 d . . .
C14 C 0.2492(2) 0.68315(16) 0.54112(14) 0.0318(4) Uani 1 1 d . . .
C15 C 0.3790(2) 0.69835(15) 0.45613(13) 0.0271(4) Uani 1 1 d . . .
C16 C 0.4705(2) 0.78608(16) 0.46085(14) 0.0319(4) Uani 1 1 d . . .
C17 C 0.4264(2) 0.85460(16) 0.54799(15) 0.0343(4) Uani 1 1 d . . .
C18 C 0.4200(2) 0.62065(15) 0.36545(13) 0.0270(4) Uani 1 1 d . . .
C19 C 0.4004(2) 0.50543(16) 0.37854(15) 0.0336(4) Uani 1 1 d . . .
C20 C 0.4451(3) 0.43464(16) 0.29358(15) 0.0349(4) Uani 1 1 d . . .
C21 C 0.5165(3) 0.58383(17) 0.18338(15) 0.0395(5) Uani 1 1 d . . .
C22 C 0.4794(3) 0.66023(17) 0.26442(15) 0.0364(5) Uani 1 1 d . . .
C23 C 0.8296(2) 0.82251(17) 0.57580(15) 0.0345(4) Uani 1 1 d . . .
C24 C 0.7540(3) 0.84181(19) 0.76313(16) 0.0446(5) Uani 1 1 d . . .
C25 C 0.8157(3) 1.01091(19) 0.64852(19) 0.0499(6) Uani 1 1 d . . .
H10A H 0.3144 1.1467 0.9785 0.045 Uiso 1 1 calc R . .
H10B H 0.1494 1.2462 1.009 0.045 Uiso 1 1 calc R . .
H10C H 0.2715 1.2489 0.8963 0.045 Uiso 1 1 calc R . .
H11A H -0.3712 1.0692 1.0183 0.042 Uiso 1 1 calc R . .
H11B H -0.2591 1.0385 0.9045 0.042 Uiso 1 1 calc R . .
H11C H -0.3832 1.162 0.9242 0.042 Uiso 1 1 calc R . .
H12A H -0.0628 1.5465 0.8437 0.063 Uiso 1 1 calc R . .
H12B H -0.0734 1.5544 0.7233 0.063 Uiso 1 1 calc R . .
H12C H 0.1084 1.5312 0.7556 0.063 Uiso 1 1 calc R . .
H13 H 0.1268 0.7442 0.6824 0.041 Uiso 1 1 calc R . .
H14 H 0.1847 0.6236 0.5416 0.038 Uiso 1 1 calc R . .
H16 H 0.5616 0.7987 0.4053 0.038 Uiso 1 1 calc R . .
H17 H 0.4892 0.9144 0.5503 0.041 Uiso 1 1 calc R . .
H19 H 0.3564 0.4754 0.4456 0.04 Uiso 1 1 calc R . .
H1O H 0.2104 0.9473 0.7339 0.049 Uiso 1 1 calc R . .
H20 H 0.4342 0.3552 0.3046 0.042 Uiso 1 1 calc R . .
H21 H 0.5536 0.6125 0.1147 0.047 Uiso 1 1 calc R . .
H22 H 0.4941 0.7387 0.2515 0.044 Uiso 1 1 calc R . .
H23 H 0.8589 0.858 0.509 0.041 Uiso 1 1 calc R . .
H24A H 0.7505 0.7589 0.7603 0.067 Uiso 1 1 calc R . .
H24B H 0.6416 0.8834 0.7973 0.067 Uiso 1 1 calc R . .
H24C H 0.8391 0.8514 0.8027 0.067 Uiso 1 1 calc R . .
H25A H 0.8405 1.0342 0.5747 0.075 Uiso 1 1 calc R . .
H25B H 0.9088 1.0221 0.6809 0.075 Uiso 1 1 calc R . .
H25C H 0.7088 1.0585 0.6836 0.075 Uiso 1 1 calc R . .
H3 H 0.0235 1.0828 1.0696 0.024 Uiso 1 1 calc R . .
H4O H -0.4136 1.3555 1.1004 0.054 Uiso 1 1 calc R . .
H5 H -0.071 1.1673 0.8169 0.028 Uiso 1 1 calc R . .
H6 H -0.0996 1.3729 0.9245 0.034 Uiso 1 1 calc R . .
H6O H 0.1159 1.36 0.5388 0.072 Uiso 1 1 calc R . .
N1 N 0.3011(2) 0.84138(14) 0.62856(12) 0.0334(4) Uani 1 1 d . . .
N2 N 0.5028(2) 0.47146(13) 0.19670(12) 0.0339(4) Uani 1 1 d . . .
N3 N 0.7996(2) 0.88882(14) 0.65804(12) 0.0352(4) Uani 1 1 d . . .
O1 O 0.14380(16) 0.98614(11) 0.78255(10) 0.0329(3) Uani 1 1 d . . .
O2 O 0.37799(16) 1.05449(13) 0.78900(11) 0.0421(4) Uani 1 1 d . . .
O3 O -0.14947(17) 1.26727(11) 1.12337(10) 0.0344(3) Uani 1 1 d . . .
O4 O -0.38420(16) 1.30211(12) 1.05690(10) 0.0360(3) Uani 1 1 d . . .
O5 O 0.0977(2) 1.22246(13) 0.66619(12) 0.0601(5) Uani 1 1 d . . .
O6 O 0.0840(2) 1.39874(12) 0.59343(11) 0.0478(4) Uani 1 1 d . . .
O7 O 0.82214(18) 0.71752(12) 0.57972(10) 0.0419(4) Uani 1 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 0.0285(10) 0.0242(9) 0.0234(9) 0.0024(7) 0.0016(7) -0.0034(7)
C2 0.0246(8) 0.0206(8) 0.0233(8) -0.0019(7) 0.0010(7) -0.0076(7)
C3 0.0212(8) 0.0212(9) 0.0176(8) -0.0029(6) 0.0000(6) -0.0057(6)
C4 0.0230(8) 0.0219(8) 0.0190(8) -0.0032(6) 0.0000(6) -0.0043(7)
C5 0.0274(9) 0.0230(8) 0.0189(8) -0.0033(6) -0.0003(7) -0.0042(7)
C6 0.0322(10) 0.0256(9) 0.0254(9) -0.0054(7) -0.0024(7) -0.0036(7)
C7 0.0335(10) 0.0269(9) 0.0290(10) 0.0002(7) -0.0060(8) -0.0057(8)
C8 0.0431(11) 0.0299(11) 0.0268(10) 0.0033(8) -0.0008(8) -0.0084(8)
C9 0.0273(9) 0.0221(9) 0.0195(8) -0.0014(7) 0.0027(7) -0.0051(7)
C10 0.0296(9) 0.0296(10) 0.0328(10) -0.0019(8) -0.0024(8) -0.0129(8)
C11 0.0261(9) 0.0273(9) 0.0304(9) -0.0063(7) -0.0055(7) -0.0041(7)
C12 0.0595(13) 0.0299(10) 0.0371(11) 0.0008(8) -0.0093(10) -0.0110(9)
C13 0.0325(10) 0.0378(11) 0.0276(10) -0.0063(8) 0.0019(8) -0.0044(8)
C14 0.0313(10) 0.0340(10) 0.0284(10) -0.0043(8) 0.0004(8) -0.0085(8)
C15 0.0289(9) 0.0245(9) 0.0254(9) -0.0036(7) -0.0018(7) -0.0021(7)
C16 0.0329(10) 0.0313(10) 0.0283(9) -0.0041(8) 0.0019(8) -0.0063(8)
C17 0.0363(10) 0.0298(10) 0.0372(10) -0.0067(8) -0.0062(8) -0.0070(8)
C18 0.0243(9) 0.0261(9) 0.0278(9) -0.0051(7) 0.0006(7) -0.0029(7)
C19 0.0398(11) 0.0304(10) 0.0292(10) 0.0003(8) -0.0019(8) -0.0097(8)
C20 0.0416(11) 0.0249(10) 0.0367(11) -0.0040(8) -0.0033(8) -0.0065(8)
C21 0.0492(12) 0.0363(11) 0.0289(10) -0.0063(8) 0.0079(9) -0.0140(9)
C22 0.0474(12) 0.0273(10) 0.0305(10) -0.0055(8) 0.0057(8) -0.0108(9)
C23 0.0349(10) 0.0378(11) 0.0313(10) -0.0010(8) -0.0067(8) -0.0080(8)
C24 0.0546(13) 0.0451(12) 0.0327(11) -0.0098(9) -0.0069(9) -0.0056(10)
C25 0.0613(14) 0.0365(12) 0.0538(14) -0.0041(10) -0.0202(11) -0.0037(10)
N1 0.0368(9) 0.0339(9) 0.0265(8) -0.0064(7) -0.0022(7) -0.0017(7)
N2 0.0323(8) 0.0305(9) 0.0357(9) -0.0106(7) 0.0019(7) -0.0052(7)
N3 0.0381(9) 0.0335(9) 0.0347(9) -0.0059(7) -0.0113(7) -0.0025(7)
O1 0.0364(7) 0.0302(7) 0.0274(7) -0.0116(5) 0.0091(5) -0.0089(6)
O2 0.0255(7) 0.0578(9) 0.0373(8) -0.0103(7) 0.0069(6) -0.0057(6)
O3 0.0418(8) 0.0312(7) 0.0305(7) -0.0112(5) -0.0099(6) -0.0014(6)
O4 0.0308(7) 0.0354(8) 0.0383(8) -0.0174(6) -0.0035(6) 0.0040(6)
O5 0.0973(13) 0.0340(9) 0.0341(8) 0.0000(6) 0.0121(8) -0.0048(8)
O6 0.0766(11) 0.0360(8) 0.0286(7) 0.0017(6) -0.0031(7) -0.0146(8)
O7 0.0517(9) 0.0407(9) 0.0334(8) -0.0054(6) -0.0041(6) -0.0123(7)

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

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 1.517(2) . ?
C2 C10 1.523(2) . ?
C3 C2 1.583(2) . ?
C3 C3 1.523(3) 2_577 ?
C3 C4 1.575(2) . ?
C3 H3 1 . ?
C4 C11 1.527(2) . ?
C5 C2 1.579(2) . ?
C5 C4 1.574(2) . ?
C5 C6 1.491(2) . ?
C5 H5 1 . ?
C6 H6 0.95 . ?
C7 C12 1.502(3) . ?
C7 C6 1.342(3) . ?
C7 C8 1.487(3) . ?
C9 C4 1.521(2) . ?
C10 H10A 0.98 . ?
C10 H10B 0.98 . ?
C10 H10C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13 0.95 . ?
C14 C13 1.382(3) . ?
C14 H14 0.95 . ?
C15 C14 1.393(2) . ?
C15 C16 1.393(2) . ?
C16 C17 1.385(3) . ?
C16 H16 0.95 . ?
C17 H17 0.95 . ?
C18 C15 1.488(2) . ?
C18 C19 1.385(3) . ?
C18 C22 1.394(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 H21 0.95 . ?
C22 C21 1.382(3) . ?
C22 H22 0.95 . ?
C23 H23 0.95 . ?
C23 N3 1.325(2) . ?
C24 H24A 0.98 . ?
C24 H24B 0.98 . ?
C24 H24C 0.98 . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
N1 C13 1.339(2) . ?
N1 C17 1.328(2) . ?
N2 C20 1.334(3) . ?
N2 C21 1.339(3) . ?
N3 C24 1.453(3) . ?
N3 C25 1.456(3) . ?
O1 C1 1.319(2) . ?
O1 H1O 0.84 . ?
O2 C1 1.214(2) . ?
O3 C9 1.207(2) . ?
O4 C9 1.331(2) . ?
O4 H4O 0.84 . ?
O5 C8 1.217(2) . ?
O6 C8 1.318(2) . ?
O6 H6O 0.84 . ?
O7 C23 1.240(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 C2 C10 110.04(14) . . ?
C1 C2 C3 118.67(13) . . ?
C1 C2 C5 112.70(14) . . ?
C1 O1 H1O 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
C2 C3 H3 109.1 . . ?
C2 C5 H5 109.4 . . ?
C3 C3 C2 120.17(16) 2_577 . ?
C3 C3 C4 117.64(16) 2_577 . ?
C3 C3 H3 109.1 2_577 . ?
C4 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
C4 C11 H11C 109.5 . . ?
C4 C3 C2 90.13(12) . . ?
C4 C3 H3 109.1 . . ?
C4 C5 C2 90.34(12) . . ?
C4 C5 H5 109.4 . . ?
C5 C2 C3 89.03(12) . . ?
C5 C4 C3 89.51(12) . . ?
C5 C6 H6 115.5 . . ?
C6 C5 C2 116.73(14) . . ?
C6 C5 C4 120.22(14) . . ?
C6 C5 H5 109.4 . . ?
C6 C7 C12 122.05(17) . . ?
C6 C7 C8 121.01(16) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
C7 C6 C5 128.96(16) . . ?
C7 C6 H6 115.5 . . ?
C8 C7 C12 116.93(16) . . ?
C8 O6 H6O 109.5 . . ?
C9 C4 C11 111.49(13) . . ?
C9 C4 C3 112.63(13) . . ?
C9 C4 C5 111.30(13) . . ?
C9 O4 H4O 109.5 . . ?
C10 C2 C3 111.62(13) . . ?
C10 C2 C5 113.46(14) . . ?
C11 C4 C3 118.05(13) . . ?
C11 C4 C5 112.01(13) . . ?
C13 C14 C15 119.22(17) . . ?
C13 C14 H14 120.4 . . ?
C14 C13 H13 118.4 . . ?
C14 C15 C16 117.64(16) . . ?
C14 C15 C18 120.49(16) . . ?
C15 C14 H14 120.4 . . ?
C15 C16 H16 120.6 . . ?
C16 C15 C18 121.85(16) . . ?
C16 C17 H17 118.1 . . ?
C17 C16 C15 118.81(17) . . ?
C17 C16 H16 120.6 . . ?
C17 N1 C13 117.43(15) . . ?
C18 C19 H19 120.2 . . ?
C18 C22 H22 120.4 . . ?
C19 C18 C15 120.92(16) . . ?
C19 C18 C22 117.33(16) . . ?
C19 C20 H20 118.2 . . ?
C20 C19 C18 119.53(17) . . ?
C20 C19 H19 120.2 . . ?
C20 N2 C21 116.94(16) . . ?
C21 C22 C18 119.16(17) . . ?
C21 C22 H22 120.4 . . ?
C22 C18 C15 121.76(16) . . ?
C22 C21 H21 118.3 . . ?
C23 N3 C24 121.30(17) . . ?
C23 N3 C25 122.17(18) . . ?
C24 N3 C25 116.50(16) . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C13 C14 123.18(17) . . ?
N1 C13 H13 118.4 . . ?
N1 C17 C16 123.71(17) . . ?
N1 C17 H17 118.1 . . ?
N2 C20 C19 123.59(17) . . ?
N2 C20 H20 118.2 . . ?
N2 C21 C22 123.38(18) . . ?
N2 C21 H21 118.3 . . ?
N3 C23 H23 117.6 . . ?
N3 C24 H24A 109.5 . . ?
N3 C24 H24B 109.5 . . ?
N3 C24 H24C 109.5 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
O1 C1 C2 113.01(14) . . ?
O2 C1 C2 123.75(16) . . ?
O2 C1 O1 123.24(16) . . ?
O3 C9 C4 124.50(15) . . ?
O3 C9 O4 123.12(15) . . ?
O4 C9 C4 112.27(14) . . ?
O5 C8 C7 124.35(17) . . ?
O5 C8 O6 121.51(17) . . ?
O6 C8 C7 114.08(16) . . ?
O7 C23 H23 117.6 . . ?
O7 C23 N3 124.76(18) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O N1 0.84 1.85 2.6679(19) 162.9 .
O4 H4O N2 0.84 1.85 2.6848(19) 175.1 1_466
O6 H6O O7 0.84 1.78 2.6225(19) 177.6 2_676