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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_creatine_form_I
_chemical_name_common            
;            
Creatine form I
;
_chemical_formula_moiety         'C4 H9 N3 O2'
_chemical_formula_sum            'C4 H9 N3 O2'
_chemical_formula_weight         131.14
_exptl_crystal_preparation       
;
Creatine Form I was prepared by slurrying an  excess ofcreatine anhydrous in
isoamyl alcohol for one week with cycle of temperature between room temperature
and 383K.The excess solid obtained was creatine form I.  
the powder produced was loaded in a 0.7 mm borosilicate glass capillary,
mounted on Bruker AXS D8 X-ray powder diffractometer equipped with 
primary monochromator (CuKa1, l = 1.54056A) and a 
Lynxeye position sensitive detector. Collection was made at room temperature.   
;

#===============================================================================
# 6. CRYSTAL DATA


_symmetry_space_group_name_H-M   Pn21a
_symmetry_cell_setting           orthorhombic

_exptl_crystal_colour            colourless
_chemical_melting_point          ?
_exptl_crystal_description       ?

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,-z
1/2-x,1/2+y,1/2+z
1/2+x,y,1/2-z


_cell_length_a                   11.9450(2)
_cell_length_b                   9.5273(1)
_cell_length_c                   5.3438(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     608.14(1)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     1.54056
_exptl_crystal_density_diffrn    1.432
_pd_proc_ls_prof_R_factor        0.034
_pd_proc_ls_prof_wR_factor       0.041
_pd_proc_ls_prof_wR_expected     0.020
_refine_ls_goodness_of_fit_all   2.099

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O17 O Uiso -0.09889(8) 0.42321(18) -0.0920(3) 1.000 0.0251 . .
O18 O Uiso -0.19383(13) 0.62120(10) -0.0112(2) 1.000 0.0251 . .
N1 N Uiso 0.07336(4) 0.49818(5) 0.21966(10) 1.000 0.0251 . .
N5 N Uiso 0.21915(5) 0.41155(4) -0.02165(11) 1.000 0.0251 . .
N6 N Uiso 0.15222(5) 0.63184(5) -0.10033(10) 1.000 0.0251 . .
C2 C Uiso 0.14729(5) 0.51441(5) 0.03441(10) 1.000 0.0251 . .
C3 C Uiso 0.08085(3) 0.37615(4) 0.38291(6) 1.000 0.0251 . .
C4 C Uiso -0.02884(3) 0.58025(5) 0.22342(8) 1.000 0.0251 . .
C10 C Uiso -0.11432(5) 0.53773(7) 0.02298(12) 1.000 0.0251 . .
H7 H Uiso 0.03301(17) 0.3898(2) 0.5139(4) 1.000 0.0301 . .
H8 H Uiso 0.06482(19) 0.2948(2) 0.3008(4) 1.000 0.0301 . .
H9 H Uiso 0.15024(16) 0.3699(3) 0.4524(4) 1.000 0.0301 . .
H11 H Uiso -0.06077(18) 0.5695(2) 0.3769(4) 1.000 0.0301 . .
H12 H Uiso -0.01430(18) 0.6729(2) 0.2076(4) 1.000 0.0301 . .
H13 H Uiso 0.21434(17) 0.3204(2) 0.0509(5) 1.000 0.0301 . .
H14 H Uiso 0.27501(17) 0.4286(3) -0.1452(5) 1.000 0.0301 . .
H15 H Uiso 0.1104(2) 0.7151(3) -0.0607(4) 1.000 0.0301 . .
H16 H Uiso 0.20773(18) 0.6384(2) -0.2269(5) 1.000 0.0301 . .

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O17 C10 1.2657(18)
O18 C10 1.2521(15)
N1 C2 1.3356(8)
N1 C3 1.4563(6)
N1 C4 1.4499(6)
N5 C2 1.3368(7)
N6 C2 1.3318(7)
N5 H13 0.953(2)
N5 H14 0.953(2)
N6 H15 0.961(3)
N6 H16 0.949(2)
C4 C10 1.5343(7)
C3 H7 0.913(2)
C3 H8 0.911(2)
C3 H9 0.910(2)
C4 H11 0.910(2)
C4 H12 0.904(2)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C3 119.73(4)
C2 N1 C4 120.30(5)
C3 N1 C4 118.29(4)
C2 N5 H13 122.57(15)
C2 N5 H14 118.69(17)
H13 N5 H14 118.7(2)
C2 N6 H15 123.45(15)
C2 N6 H16 118.13(13)
H15 N6 H16 117.76(19)
N5 C2 N6 117.80(5)
N1 C2 N5 120.39(5)
N1 C2 N6 121.82(5)
N1 C4 C10 114.10(4)
O18 C10 C4 116.04(7)
O17 C10 O18 125.96(9)
O17 C10 C4 118.01(7)
N1 C3 H7 107.89(13)
N1 C3 H8 112.20(14)
N1 C3 H9 110.65(17)
H7 C3 H8 111.04(19)
H7 C3 H9 105.46(19)
H8 C3 H9 109.4(2)
N1 C4 H11 107.73(14)
N1 C4 H12 111.33(14)
C10 C4 H11 108.69(14)
C10 C4 H12 108.70(14)
H11 C4 H12 105.95(19)

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
C3 N1 C2 N5 8.31(8)
C3 N1 C2 N6 -171.83(5)
C4 N1 C2 N5 -156.68(5)
C4 N1 C2 N6 23.19(8)
C2 N1 C4 C10 71.29(6)
C3 N1 C4 C10 -93.91(5)
N1 C4 C10 O17 12.78(10)
N1 C4 C10 O18 -167.24(8)

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
#
#D H A D - H H...A D...A D-H...A symm(A)
#
N5 H13 O18 0.953(2) 1.925(2) 2.7883(10) 149.5(2) 2_545
N5 H14 O17 0.953(2) 2.060(3) 2.9998(14) 168.6(3) 4_554
N6 H15 O17 0.961(3) 2.149(3) 3.0279(17) 151.5(2) 2_555
N6 H16 O18 0.949(2) 1.835(3) 2.7751(14) 170.08(19) 4_554
_refine_special_details          
;
A restrained Rietveld refinement was carried out using the best solution 
returned from the simulated annealing in TOPAS V4.1. The final refinement 
included a total of 97 parameters (29 profile, 3 cell, 1 scale, 1 isotropic 
temperature factor, 9 preferred orientation, 54 coordinates), yielding a final 
Rwp= 4.132.
The resulting structure was further scrutinised by allowing all fractional 
coordinates to refine freely (97 parameters, Rwp = 3.00). As expected, the 
improve Rwp came at the expense of some chemical sense, but otherwise, the 
geometry of the independent molecules was well preserved, confirming the 
correctness of the constrained refined crystal structure.
;
_database_code_depnum_ccdc_archive 'CCDC 990914'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_creatine_form_II
_chemical_name_common            
;            
Creatine form II
;
_chemical_formula_moiety         'C4 H9 N3 O2'
_chemical_formula_sum            'C4 H9 N3 O2'
_chemical_formula_weight         131.14
_exptl_crystal_colour            colourless
_chemical_melting_point          ?
_exptl_crystal_description       ?
_exptl_crystal_preparation       
;
Creatine Form II was prepared by slurrying an  excess of creatine anhydrous in
butylacetate for two week with cycles of temperature between room temperature
and 383K.The excess solid obtained was creatine form II.  
the powder produced was loaded in a 0.7 mm borosilicate glass capillary,
mounted on Bruker AXS D8 X-ray powder diffractometer equipped with 
primary monochromator (CuKa1, l = 1.54056A) and a 
Lynxeye position sensitive detector. Collection was made at room temperature.   
;

#===============================================================================
# 6. CRYSTAL DATA
_symmetry_space_group_name_H-M   P21/c
_symmetry_cell_setting           monoclinic

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z


_cell_length_a                   9.8450(3)
_cell_length_b                   5.8373(2)
_cell_length_c                   11.6698(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.723(2)
_cell_angle_gamma                90
_cell_volume                     645.55(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_diffrn_radiation_wavelength     1.54056
_diffrn_ambient_temperature      298(2)
_exptl_crystal_density_diffrn    1.349
_pd_proc_ls_prof_R_factor        0.037
_pd_proc_ls_prof_wR_factor       0.040
_pd_proc_ls_prof_wR_expected     0.011
_refine_ls_goodness_of_fit_all   3.538

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O17 O Uiso 0.16394(4) -0.0591(2) -0.13061(6) 1.000 0.0384 . .
O18 O Uiso 0.36872(7) 0.0273(2) -0.16701(5) 1.000 0.0384 . .
N1 N Uiso 0.23350(6) 0.16810(4) 0.08278(2) 1.000 0.0384 . .
N5 N Uiso 0.14038(5) -0.06285(5) 0.20427(6) 1.000 0.0384 . .
N6 N Uiso 0.35959(1) -0.14457(4) 0.18037(2) 1.000 0.0384 . .
C2 C Uiso 0.24433(6) -0.01233(6) 0.15451(3) 1.000 0.0384 . .
C3 C Uiso 0.11617(1) 0.32630(4) 0.06813(2) 1.000 0.0384 . .
C4 C Uiso 0.32463(3) 0.18916(3) 0.00483(3) 1.000 0.0384 . .
C10 C Uiso 0.28407(4) 0.03274(10) -0.10443(2) 1.000 0.0384 . .
H7 H Uiso 0.11992(2) 0.43109(3) 0.00660(1) 1.000 0.0461 . .
H8 H Uiso 0.02774(2) 0.24936(10) 0.05041(6) 1.000 0.0461 . .
H9 H Uiso 0.12697(7) 0.41669(7) 0.13787(2) 1.000 0.0461 . .
H11 H Uiso 0.32065(2) 0.34393(5) -0.02122(6) 1.000 0.0461 . .
H12 H Uiso 0.42067(4) 0.16102(4) 0.04627(5) 1.000 0.0461 . .
H13 H Uiso 0.05779(19) 0.0144(3) 0.18784(16) 1.000 0.0461 . .
H14 H Uiso 0.15056(5) -0.18428(17) 0.25333(15) 1.000 0.0461 . .
H15 H Uiso 0.43468(4) -0.12065(5) 0.15185(7) 1.000 0.0461 . .
H16 H Uiso 0.36383(17) -0.2615(2) 0.23124(15) 1.000 0.0461 . .

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O17 C10 1.2584(8)
O18 C10 1.2485(8)
N1 C2 1.3315(4)
N1 C3 1.4523(5)
N1 C4 1.4456(6)
N5 C2 1.3392(8)
N6 C2 1.3375(6)
N5 H13 0.904(2)
N5 H14 0.8995(14)
N6 H15 0.9001(5)
N6 H16 0.8981(14)
C4 C10 1.5307(5)
C3 H7 0.9516(3)
C3 H8 0.9512(4)
C3 H9 0.9514(4)
C4 H11 0.9506(4)
C4 H12 0.9524(6)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 N1 C3 120.17(5)
C2 N1 C4 120.35(4)
C3 N1 C4 118.77(2)
C2 N5 H13 123.19(13)
C2 N5 H14 118.89(7)
H13 N5 H14 117.83(14)
C2 N6 H15 123.96(4)
C2 N6 H16 118.19(11)
H15 N6 H16 117.81(12)
N5 C2 N6 118.45(3)
N1 C2 N5 120.42(5)
N1 C2 N6 121.12(5)
N1 C4 C10 114.03(3)
O18 C10 C4 115.95(5)
O17 C10 O18 125.42(6)
O17 C10 C4 118.18(4)
N1 C3 H7 107.78(2)
N1 C3 H8 112.16(4)
N1 C3 H9 110.55(4)
H7 C3 H8 111.09(5)
H7 C3 H9 105.71(3)
H8 C3 H9 109.35(6)
N1 C4 H11 107.65(4)
N1 C4 H12 111.46(4)
C10 C4 H11 108.77(5)
C10 C4 H12 108.61(4)
H11 C4 H12 105.99(4)

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
C3 N1 C2 N5 6.79(5)
C3 N1 C2 N6 -171.97(3)
C4 N1 C2 N5 -163.41(4)
C4 N1 C2 N6 17.83(5)
C2 N1 C4 C10 75.64(5)
C3 N1 C4 C10 -94.70(3)
N1 C4 C10 O17 14.80(7)
N1 C4 C10 O18 -172.48(6)

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
#
#D H A D - H H...A D...A D-H...A symm(A)
#
N5 H13 O17 0.904(2) 2.119(2) 2.9709(8) 156.81(16) 3_555
N5 H14 O17 0.8995(14) 1.9997(17) 2.8973(11) 175.47(11) 4_545
N6 H15 O18 0.9001(5) 1.9720(9) 2.8060(8) 153.41(7) 3_655
N6 H16 O18 0.8981(14) 1.9464(17) 2.8434(10) 176.45(14) 4_545
C3 H8 O17 0.9512(4) 2.5744(8) 3.4145(7) 147.41(6) 3_555
C4 H12 O18 0.9524(6) 2.4310(9) 3.3460(8) 161.05(4) 3_655
_refine_special_details          
;
A restrained Rietveld refinement was carried out using the best solution 
returned from the simulated annealing in TOPAS V4.1. The final refinement 
included a total of 112 parameters (44 profile, 4 cell, 1 scale, 1 isotropic 
temperature factor, 8 preferred orientation, 54 coordinates), yielding a final 
Rwp= 3.967.
The resulting structure was further scrutinised by allowing all fractional 
coordinates to refine freely (112 parameters, Rwp = 2.887). As expected, the 
improve Rwp came at the expense of some chemical sense, but otherwise, the 
geometry of the independent molecules was well preserved, confirming the 
correctness of the constrained refined crystal structure.
;
_database_code_depnum_ccdc_archive 'CCDC 990915'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_creatine_formicacid_solvate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            'Creatine formic acid solvate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N3 O2, C H2 O2'
_chemical_formula_sum            'C5 H11 N3 O4'
_chemical_formula_weight         177.17

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.4929(14)
_cell_length_b                   4.7791(4)
_cell_length_c                   10.1101(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     845.21(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    1864
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      32.17

_exptl_crystal_description       'Cut slab'
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_max          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791009
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   SADABS

_exptl_special_details           ?

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6976
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0447
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         34.25
_reflns_number_total             3138
_reflns_number_gt                2502
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² 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/[σ²(Fo²)+(0.0439P)²+0.0825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.5(10)
_refine_ls_number_reflns         3138
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1 O 0.18924(6) 0.4081(2) 0.31388(10) 0.0200(2) Uani 1 1 d . . .
O2 O 0.15049(6) 0.6539(2) 0.13964(9) 0.0227(2) Uani 1 1 d . . .
O3 O 0.07484(7) 0.0019(2) 1.00239(12) 0.0272(2) Uani 1 1 d . . .
O4 O 0.10067(7) 0.2782(3) 0.83326(11) 0.0305(3) Uani 1 1 d . . .
N1 N 0.21487(7) 0.9771(3) 0.50372(12) 0.0190(2) Uani 1 1 d . . .
N2 N 0.18546(8) 0.6671(3) 0.66881(11) 0.0194(3) Uani 1 1 d . . .
N3 N 0.10353(7) 0.7139(2) 0.48925(10) 0.0156(2) Uani 1 1 d . . .
C1 C 0.16748(8) 0.7847(3) 0.55374(13) 0.0154(2) Uani 1 1 d . . .
C2 C 0.05193(9) 0.5041(3) 0.54511(15) 0.0208(3) Uani 1 1 d . . .
H2A H 0.0082 0.4777 0.4858 0.031 Uiso 1 1 calc R . .
H2B H 0.0337 0.5676 0.6317 0.031 Uiso 1 1 calc R . .
H2C H 0.0793 0.3264 0.5553 0.031 Uiso 1 1 calc R . .
C3 C 0.09676(8) 0.7746(3) 0.34781(12) 0.0160(2) Uani 1 1 d . . .
H3A H 0.1084 0.9748 0.3328 0.019 Uiso 1 1 calc R . .
H3B H 0.0433 0.7417 0.3198 0.019 Uiso 1 1 calc R . .
C4 C 0.15005(8) 0.5966(3) 0.26185(12) 0.0156(2) Uani 1 1 d . . .
C5 C 0.12195(9) 0.1151(3) 0.91749(14) 0.0207(3) Uani 1 1 d . . .
H5 H 0.1746 0.0680 0.9219 0.025 Uiso 1 1 calc R . .
H1C H 0.0990(12) -0.126(4) 1.050(2) 0.032(5) Uiso 1 1 d . . .
H1N H 0.1957(12) 1.100(5) 0.446(2) 0.036(6) Uiso 1 1 d . . .
H2N H 0.2566(12) 1.012(4) 0.549(2) 0.022(4) Uiso 1 1 d . . .
H3N H 0.2257(11) 0.732(4) 0.7092(17) 0.017(4) Uiso 1 1 d . . .
H4N H 0.1615(12) 0.540(4) 0.694(2) 0.024(5) Uiso 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
O1 0.0236(5) 0.0196(5) 0.0167(4) 0.0058(4) 0.0023(4) 0.0051(4)
O2 0.0267(6) 0.0285(6) 0.0128(4) 0.0061(4) 0.0022(4) 0.0067(4)
O3 0.0214(5) 0.0323(6) 0.0279(5) 0.0174(5) 0.0026(4) 0.0034(5)
O4 0.0282(6) 0.0359(7) 0.0275(6) 0.0179(5) 0.0003(5) -0.0005(5)
N1 0.0203(6) 0.0196(6) 0.0171(5) 0.0063(5) -0.0045(5) -0.0033(5)
N2 0.0238(7) 0.0201(6) 0.0144(5) 0.0060(4) -0.0042(4) -0.0049(5)
N3 0.0158(6) 0.0185(5) 0.0124(4) 0.0026(4) 0.0009(4) -0.0006(4)
C1 0.0188(6) 0.0147(6) 0.0127(5) 0.0016(5) 0.0009(4) 0.0016(5)
C2 0.0187(7) 0.0232(7) 0.0204(5) 0.0047(5) 0.0008(5) -0.0037(5)
C3 0.0167(6) 0.0184(6) 0.0128(5) 0.0030(5) -0.0018(5) 0.0018(5)
C4 0.0170(6) 0.0163(6) 0.0135(5) 0.0031(5) -0.0001(4) -0.0019(5)
C5 0.0173(6) 0.0249(7) 0.0200(6) 0.0051(6) -0.0015(5) -0.0011(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2484(16) . ?
O2 C4 1.2655(15) . ?
O3 C5 1.3071(18) . ?
O3 H1C 0.89(2) . ?
O4 C5 1.2129(18) . ?
N1 C1 1.3374(18) . ?
N1 H1N 0.90(2) . ?
N1 H2N 0.88(2) . ?
N2 C1 1.3297(17) . ?
N2 H3N 0.870(19) . ?
N2 H4N 0.78(2) . ?
N3 C1 1.3383(18) . ?
N3 C2 1.4627(18) . ?
N3 C3 1.4639(16) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.5322(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 H5 0.9500 . ?

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
C5 O3 H1C 110.1(13) . . ?
C1 N1 H1N 117.8(14) . . ?
C1 N1 H2N 116.4(13) . . ?
H1N N1 H2N 122(2) . . ?
C1 N2 H3N 116.8(12) . . ?
C1 N2 H4N 119.0(15) . . ?
H3N N2 H4N 124.1(19) . . ?
C1 N3 C2 120.07(11) . . ?
C1 N3 C3 119.56(11) . . ?
C2 N3 C3 117.58(11) . . ?
N2 C1 N1 118.35(13) . . ?
N2 C1 N3 121.14(12) . . ?
N1 C1 N3 120.51(11) . . ?
N3 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N3 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N3 C3 C4 113.26(11) . . ?
N3 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N3 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 O2 124.33(13) . . ?
O1 C4 C3 119.72(11) . . ?
O2 C4 C3 115.95(12) . . ?
O4 C5 O3 122.25(15) . . ?
O4 C5 H5 118.9 . . ?
O3 C5 H5 118.9 . . ?

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
C2 N3 C1 N2 0.0(2) . . . . ?
C3 N3 C1 N2 -160.64(13) . . . . ?
C2 N3 C1 N1 -179.73(13) . . . . ?
C3 N3 C1 N1 19.60(19) . . . . ?
C1 N3 C3 C4 68.96(15) . . . . ?
C2 N3 C3 C4 -92.18(15) . . . . ?
N3 C3 C4 O1 5.08(18) . . . . ?
N3 C3 C4 O2 -175.25(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.941
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.051

#===END

_database_code_depnum_ccdc_archive 'CCDC 990916'
