Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006


data_global

_journal_coden_Cambridge         1350

# Attachment 'Desiraju_Submit_CIF_27_June.cif'

# SUBMISSION DETAILS
_publ_contact_author_name        'Professor Gautam R. Desiraju'
_publ_contact_author_address     
; School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;
_publ_contact_author_email       gautam_desiraju@yahoo.com
_publ_contact_author_phone       '91 40 23010500 extn. 4828'
_publ_contact_author_fax         '91 40 3010567'
_publ_requested_journal          CrystEngComm
# TITLE AND AUTHOR LIST
_publ_section_title              
;
Crystal Structure Prediction of Aminophenols with the
Supramolecular Synthon Approach: Experimental Verifications
;
loop_
_publ_author_name
_publ_author_address
'Archan Dey'
;School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;
'Narendra Nath Pati'
;School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;
'Gautam R. Desiraju'
;School of Chemistry
University of Hyderabad
Hyderabad 500 046,
India
;

data_1
_database_code_depnum_ccdc_archive 'CCDC 612505'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
2-amino-4-ethylphenol
;
_chemical_name_common            2-amino-4-ethylphenol
_chemical_melting_point          408
_chemical_formula_moiety         C8H11NO
_chemical_formula_sum            'C8 H11 N O'
_chemical_formula_weight         137.18

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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.806(13)
_cell_length_b                   7.155(6)
_cell_length_c                   7.820(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.861(14)
_cell_angle_gamma                90.00
_cell_volume                     825.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    585
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      25.62

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.104
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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            6353
_diffrn_reflns_av_R_equivalents  0.1867
_diffrn_reflns_av_sigmaI/netI    0.1683
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1460
_reflns_number_gt                663
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^ > 2sigma(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^)+(0.1099P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.017(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         1460
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1872
_refine_ls_R_factor_gt           0.0806
_refine_ls_wR_factor_ref         0.2201
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   0.927
_refine_ls_restrained_S_all      0.927
_refine_ls_shift/su_max          0.000
_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 0.0050(2) 0.0640(4) 0.2673(3) 0.0282(9) Uani 1 1 d . . .
C1 C 0.2393(3) -0.1015(6) 0.2820(5) 0.0256(12) Uani 1 1 d . . .
H1 H 0.2762 -0.1905 0.3450 0.031 Uiso 1 1 calc R . .
N1 N 0.1072(3) -0.1990(5) 0.4382(4) 0.0261(11) Uani 1 1 d . . .
C2 C 0.0930(3) 0.0520(6) 0.2280(5) 0.0224(11) Uani 1 1 d . . .
C3 C 0.2773(3) 0.0063(6) 0.1528(5) 0.0253(12) Uani 1 1 d . . .
C4 C 0.1497(3) -0.0800(6) 0.3184(4) 0.0221(11) Uani 1 1 d . . .
C5 C 0.2192(3) 0.1377(6) 0.0634(5) 0.0312(13) Uani 1 1 d . . .
H5 H 0.2423 0.2125 -0.0234 0.037 Uiso 1 1 calc R . .
C6 C 0.1293(3) 0.1601(6) 0.0994(5) 0.0301(13) Uani 1 1 d . . .
H6 H 0.0921 0.2490 0.0367 0.036 Uiso 1 1 calc R . .
C7 C 0.3754(3) -0.0129(6) 0.1198(5) 0.0335(13) Uani 1 1 d . . .
H7A H 0.3829 0.0265 0.0005 0.040 Uiso 1 1 calc R . .
H7B H 0.3928 -0.1463 0.1303 0.040 Uiso 1 1 calc R . .
C8 C 0.4396(4) 0.1020(9) 0.2421(8) 0.076(2) Uani 1 1 d . . .
H8A H 0.4236 0.2346 0.2312 0.113 Uiso 1 1 calc R . .
H8B H 0.5021 0.0840 0.2130 0.113 Uiso 1 1 calc R . .
H8C H 0.4342 0.0610 0.3604 0.113 Uiso 1 1 calc R . .
H2A H 0.154(2) -0.260(5) 0.494(5) 0.017(11) Uiso 1 1 d . . .
H1A H 0.058(3) -0.117(6) 0.514(5) 0.047(13) Uiso 1 1 d . . .
H3A H -0.028(3) 0.130(7) 0.191(6) 0.046(16) 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 0.056(2) 0.020(2) 0.0083(15) 0.0010(13) 0.0006(15) 0.0069(16)
C1 0.049(3) 0.016(3) 0.011(2) -0.0015(18) 0.001(2) 0.004(2)
N1 0.051(3) 0.017(2) 0.0107(18) 0.0052(17) 0.0031(18) 0.003(2)
C2 0.042(3) 0.017(3) 0.008(2) -0.0011(17) 0.0031(19) 0.003(2)
C3 0.047(3) 0.016(3) 0.013(2) 0.003(2) 0.004(2) 0.000(2)
C4 0.049(3) 0.012(3) 0.005(2) -0.0023(17) 0.000(2) -0.004(2)
C5 0.064(4) 0.019(3) 0.012(2) 0.0039(19) 0.010(2) -0.002(2)
C6 0.055(3) 0.022(3) 0.014(2) 0.0056(19) 0.007(2) 0.004(2)
C7 0.059(4) 0.023(3) 0.020(2) 0.002(2) 0.007(2) 0.000(2)
C8 0.069(4) 0.082(5) 0.078(4) -0.044(4) 0.021(3) -0.017(4)

_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 C2 1.368(5) . ?
O1 H3A 0.87(5) . ?
C1 C4 1.388(6) . ?
C1 C3 1.424(6) . ?
C1 H1 0.9500 . ?
N1 C4 1.449(5) . ?
N1 H2A 0.90(4) . ?
N1 H1A 1.15(4) . ?
C2 C6 1.411(6) . ?
C2 C4 1.413(5) . ?
C3 C5 1.418(6) . ?
C3 C7 1.503(6) . ?
C5 C6 1.393(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.530(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C2 O1 H3A 112(3) . . ?
C4 C1 C3 121.8(4) . . ?
C4 C1 H1 119.1 . . ?
C3 C1 H1 119.1 . . ?
C4 N1 H2A 104(2) . . ?
C4 N1 H1A 112(2) . . ?
H2A N1 H1A 120(3) . . ?
O1 C2 C6 123.6(4) . . ?
O1 C2 C4 117.8(4) . . ?
C6 C2 C4 118.5(4) . . ?
C5 C3 C1 116.7(4) . . ?
C5 C3 C7 122.0(4) . . ?
C1 C3 C7 121.2(4) . . ?
C1 C4 C2 120.6(4) . . ?
C1 C4 N1 122.9(4) . . ?
C2 C4 N1 116.4(4) . . ?
C6 C5 C3 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C3 C5 H5 119.1 . . ?
C5 C6 C2 120.6(4) . . ?
C5 C6 H6 119.7 . . ?
C2 C6 H6 119.7 . . ?
C3 C7 C8 113.7(4) . . ?
C3 C7 H7A 108.8 . . ?
C8 C7 H7A 108.8 . . ?
C3 C7 H7B 108.8 . . ?
C8 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.076

data_2
_database_code_depnum_ccdc_archive 'CCDC 612506'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
3 amino 2 naphthol
;
_chemical_name_common            '3 amino 2 naphthol'
_chemical_melting_point          483
_chemical_formula_moiety         'C10 H9 N O'
_chemical_formula_sum            'C10 H9 N O'
_chemical_formula_weight         159.18

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 0.0000 0.0000 '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 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/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, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1054(13)
_cell_length_b                   6.0153(5)
_cell_length_c                   8.4629(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.5820(10)
_cell_angle_gamma                90.00
_cell_volume                     758.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2785
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.98

_exptl_crystal_description       Block
_exptl_crystal_colour            'pale brown'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus 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            4619
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         26.01
_reflns_number_total             1493
_reflns_number_gt                1388
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^ > 2sigma(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^)+(0.0636P)^2^+0.3090P] where P=(Fo^2^+2Fc^2^)/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_number_reflns         1493
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_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 0.52585(6) 1.10247(16) 0.33309(10) 0.0191(3) Uani 1 1 d . . .
C1 C 0.66197(8) 1.1861(2) 0.23122(14) 0.0160(3) Uani 1 1 d . . .
H1 H 0.6387 1.3260 0.1920 0.019 Uiso 1 1 calc R . .
C2 C 0.72953(8) 0.7743(2) 0.35138(13) 0.0155(3) Uani 1 1 d . . .
H2 H 0.7521 0.6350 0.3930 0.019 Uiso 1 1 calc R . .
C3 C 0.87031(8) 0.8452(2) 0.24414(15) 0.0181(3) Uani 1 1 d . . .
H3 H 0.8940 0.7066 0.2853 0.022 Uiso 1 1 calc R . .
C4 C 0.74936(8) 1.1203(2) 0.20747(13) 0.0153(3) Uani 1 1 d . . .
C5 C 0.78336(8) 0.9111(2) 0.26850(13) 0.0152(3) Uani 1 1 d . . .
C6 C 0.64544(8) 0.8409(2) 0.37207(13) 0.0148(3) Uani 1 1 d . . .
C7 C 0.80303(8) 1.2550(2) 0.12356(14) 0.0177(3) Uani 1 1 d . . .
H7 H 0.7809 1.3951 0.0826 0.021 Uiso 1 1 calc R . .
N1 N 0.58585(7) 0.7032(2) 0.44015(12) 0.0172(3) Uani 1 1 d . . .
C8 C 0.61119(8) 1.0501(2) 0.31000(13) 0.0155(3) Uani 1 1 d . . .
C9 C 0.88655(8) 1.1857(2) 0.10079(15) 0.0201(3) Uani 1 1 d . . .
H9 H 0.9216 1.2772 0.0436 0.024 Uiso 1 1 calc R . .
C10 C 0.92060(8) 0.9787(2) 0.16211(15) 0.0204(3) Uani 1 1 d . . .
H10 H 0.9786 0.9318 0.1465 0.025 Uiso 1 1 calc R . .
H2A H 0.6146(11) 0.591(3) 0.4961(18) 0.026(4) Uiso 1 1 d . . .
H1A H 0.4929(13) 1.134(3) 0.238(3) 0.045(5) Uiso 1 1 d . . .
H3A H 0.5495(11) 0.781(3) 0.4973(19) 0.028(4) 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 0.0148(5) 0.0268(6) 0.0162(5) 0.0025(4) 0.0035(3) 0.0051(4)
C1 0.0180(6) 0.0149(6) 0.0141(6) -0.0004(5) -0.0004(5) 0.0018(5)
C2 0.0164(6) 0.0146(6) 0.0142(6) -0.0009(5) -0.0012(5) 0.0007(5)
C3 0.0158(6) 0.0176(7) 0.0198(6) -0.0008(5) 0.0001(5) 0.0016(5)
C4 0.0148(6) 0.0171(7) 0.0130(6) -0.0024(5) -0.0004(4) -0.0010(5)
C5 0.0147(6) 0.0165(6) 0.0132(6) -0.0026(5) -0.0006(4) -0.0009(5)
C6 0.0149(6) 0.0175(6) 0.0111(5) -0.0024(5) -0.0001(4) -0.0030(5)
C7 0.0186(6) 0.0166(6) 0.0170(6) 0.0000(5) 0.0002(5) -0.0019(5)
N1 0.0159(5) 0.0188(6) 0.0169(5) 0.0018(4) 0.0029(4) 0.0000(4)
C8 0.0133(6) 0.0200(7) 0.0122(6) -0.0033(5) -0.0004(4) 0.0019(5)
C9 0.0176(6) 0.0235(7) 0.0194(6) -0.0001(5) 0.0035(5) -0.0061(5)
C10 0.0128(6) 0.0264(7) 0.0220(6) -0.0021(5) 0.0028(5) -0.0001(5)

_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 C8 1.3722(14) . ?
O1 H1A 0.89(2) . ?
C1 C8 1.3685(18) . ?
C1 C4 1.4242(16) . ?
C1 H1 0.9500 . ?
C2 C6 1.3706(16) . ?
C2 C5 1.4214(17) . ?
C2 H2 0.9500 . ?
C3 C10 1.3710(18) . ?
C3 C5 1.4194(16) . ?
C3 H3 0.9500 . ?
C4 C7 1.4179(17) . ?
C4 C5 1.4231(18) . ?
C6 N1 1.4145(16) . ?
C6 C8 1.4272(18) . ?
C7 C9 1.3724(18) . ?
C7 H7 0.9500 . ?
N1 H2A 0.893(17) . ?
N1 H3A 0.917(17) . ?
C9 C10 1.413(2) . ?
C9 H9 0.9500 . ?
C10 H10 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
C8 O1 H1A 108.4(12) . . ?
C8 C1 C4 120.68(12) . . ?
C8 C1 H1 119.7 . . ?
C4 C1 H1 119.7 . . ?
C6 C2 C5 120.81(12) . . ?
C6 C2 H2 119.6 . . ?
C5 C2 H2 119.6 . . ?
C10 C3 C5 120.93(12) . . ?
C10 C3 H3 119.5 . . ?
C5 C3 H3 119.5 . . ?
C7 C4 C5 119.04(11) . . ?
C7 C4 C1 122.16(12) . . ?
C5 C4 C1 118.80(11) . . ?
C3 C5 C2 121.94(12) . . ?
C3 C5 C4 118.75(11) . . ?
C2 C5 C4 119.30(11) . . ?
C2 C6 N1 123.16(12) . . ?
C2 C6 C8 119.85(11) . . ?
N1 C6 C8 116.74(11) . . ?
C9 C7 C4 120.80(12) . . ?
C9 C7 H7 119.6 . . ?
C4 C7 H7 119.6 . . ?
C6 N1 H2A 111.8(10) . . ?
C6 N1 H3A 113.3(10) . . ?
H2A N1 H3A 112.6(14) . . ?
C1 C8 O1 123.24(11) . . ?
C1 C8 C6 120.55(11) . . ?
O1 C8 C6 116.21(11) . . ?
C7 C9 C10 120.23(12) . . ?
C7 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C3 C10 C9 120.25(11) . . ?
C3 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.060


