# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1420248'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2015-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-Hydroxy-N-cyclohexylphthalimide
_chemical_name_common            3HNHPI
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless

_diffrn_ambient_temperature      173(2)
_diffrn_ambient_pressure         101.3
_chemical_formula_weight         245.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0000 '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 0.0311 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 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   'C m c 21'
_symmetry_space_group_name_Hall  'C 2c -2'
_symmetry_int_tables_number      36
_chemical_absolute_configuration ?

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

_cell_length_a                   6.6923(2)
_cell_length_b                   7.5956(2)
_cell_length_c                   22.7742(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1157.66(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6308
_cell_measurement_theta_min      3.88
_cell_measurement_theta_max      68.00
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_absorpt_coefficient_mu    0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6266
_exptl_absorpt_correction_T_max  0.9453
_exptl_absorpt_process_details   'abscor Higashi RIGAKU'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'fine-focus rotating anode x-ray'
_diffrn_source_type              RIGAKU
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-II'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6308
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0329
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.88
_diffrn_reflns_theta_max         68.00
_reflns_number_total             590
_reflns_number_gt                553
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_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 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 > 2σ(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)+(0.0658P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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   -10(10)
_refine_ls_number_reflns         590
_refine_ls_number_parameters     103
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0933
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.112
_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 0.0000 -0.0926(4) 0.17896(13) 0.0356(7) Uani 1 2 d S . .
H1 H 0.0000 -0.1153 0.2151 0.053 Uiso 1 2 calc SR . .
C2 C 0.0000 0.0829(5) 0.17112(18) 0.0288(9) Uani 1 2 d S . .
C3 C 0.0000 0.1497(6) 0.11371(18) 0.0371(10) Uani 1 2 d S . .
H3 H 0.0000 0.0703 0.0815 0.045 Uiso 1 2 calc SR . .
C4 C 0.0000 0.3299(6) 0.10310(18) 0.0388(11) Uani 1 2 d S . .
H4 H 0.0000 0.3705 0.0636 0.047 Uiso 1 2 calc SR . .
C5 C 0.0000 0.4538(5) 0.14878(18) 0.0311(9) Uani 1 2 d S . .
H5 H 0.0000 0.5769 0.1415 0.037 Uiso 1 2 calc SR . .
C6 C 0.0000 0.3853(5) 0.20490(16) 0.0258(8) Uani 1 2 d S . .
C7 C 0.0000 0.2058(5) 0.21586(16) 0.0253(8) Uani 1 2 d S . .
C8 C 0.0000 0.4763(5) 0.26324(15) 0.0245(8) Uani 1 2 d S . .
O9 O 0.0000 0.6332(4) 0.27355(12) 0.0325(7) Uani 1 2 d S . .
N10 N 0.0000 0.3438(4) 0.30578(14) 0.0241(7) Uani 1 2 d S . .
C11 C 0.0000 0.1772(4) 0.28000(17) 0.0249(8) Uani 1 2 d S . .
O12 O 0.0000 0.0357(3) 0.30537(13) 0.0318(6) Uani 1 2 d S . .
C13 C 0.0000 0.3778(5) 0.36959(15) 0.0236(8) Uani 1 2 d S . .
H13 H 0.0000 0.5083 0.3754 0.028 Uiso 1 2 calc SR . .
C14 C -0.1886(4) 0.3049(3) 0.39840(12) 0.0262(6) Uani 1 1 d . . .
H14A H -0.1959 0.1762 0.3918 0.039 Uiso 1 1 calc R . .
H14B H -0.3078 0.3595 0.3802 0.039 Uiso 1 1 calc R . .
C15 C -0.1877(4) 0.3430(4) 0.46447(11) 0.0298(7) Uani 1 1 d . . .
H15A H -0.1937 0.4718 0.4709 0.045 Uiso 1 1 calc R . .
H15B H -0.3075 0.2896 0.4827 0.045 Uiso 1 1 calc R . .
C16 C 0.0000 0.2690(5) 0.49371(18) 0.0288(8) Uani 1 2 d S . .
H16A H 0.0000 0.3004 0.5359 0.035 Uiso 1 2 calc SR . .
H16B H 0.0000 0.1390 0.4905 0.035 Uiso 1 2 calc SR . .


_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
O1 C2 1.345(5) . ?
O1 H1 0.8400 . ?
C2 C7 1.382(5) . ?
C2 C3 1.402(6) . ?
C3 C4 1.390(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.402(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(5) . ?
C6 C8 1.498(5) . ?
C7 C11 1.477(5) . ?
C8 O9 1.215(5) . ?
C8 N10 1.397(5) . ?
N10 C11 1.395(4) . ?
N10 C13 1.476(5) . ?
C11 O12 1.220(4) . ?
C13 C14 1.526(3) . ?
C13 C14 1.526(3) 3 ?
C13 H13 1.0000 . ?
C14 C15 1.532(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.529(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C15 1.529(4) 3 ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?

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 H1 109.5 . . ?
O1 C2 C7 124.9(4) . . ?
O1 C2 C3 118.8(4) . . ?
C7 C2 C3 116.3(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 122.1(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 115.7(4) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
C5 C6 C7 122.5(3) . . ?
C5 C6 C8 130.4(4) . . ?
C7 C6 C8 107.1(3) . . ?
C2 C7 C6 122.1(4) . . ?
C2 C7 C11 129.1(3) . . ?
C6 C7 C11 108.8(3) . . ?
O9 C8 N10 124.9(3) . . ?
O9 C8 C6 128.6(3) . . ?
N10 C8 C6 106.4(3) . . ?
C11 N10 C8 111.2(3) . . ?
C11 N10 C13 125.0(3) . . ?
C8 N10 C13 123.8(3) . . ?
O12 C11 N10 126.9(3) . . ?
O12 C11 C7 126.7(3) . . ?
N10 C11 C7 106.4(3) . . ?
N10 C13 C14 111.09(18) . . ?
N10 C13 C14 111.09(18) . 3 ?
C14 C13 C14 111.5(3) . 3 ?
N10 C13 H13 107.6 . . ?
C14 C13 H13 107.6 . . ?
C14 C13 H13 107.6 3 . ?
C13 C14 C15 110.5(2) . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C15 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C16 C15 C14 111.2(2) . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C15 110.5(3) 3 . ?
C15 C16 H16A 109.5 3 . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 3 . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?

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
O1 C2 C3 C4 180.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
C4 C5 C6 C8 180.0 . . . . ?
O1 C2 C7 C6 180.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
O1 C2 C7 C11 0.0 . . . . ?
C3 C2 C7 C11 180.0 . . . . ?
C5 C6 C7 C2 0.000(1) . . . . ?
C8 C6 C7 C2 180.0 . . . . ?
C5 C6 C7 C11 180.0 . . . . ?
C8 C6 C7 C11 0.0 . . . . ?
C5 C6 C8 O9 0.000(1) . . . . ?
C7 C6 C8 O9 180.0 . . . . ?
C5 C6 C8 N10 180.0 . . . . ?
C7 C6 C8 N10 0.0 . . . . ?
O9 C8 N10 C11 180.000(1) . . . . ?
C6 C8 N10 C11 0.0 . . . . ?
O9 C8 N10 C13 0.000(2) . . . . ?
C6 C8 N10 C13 180.000(1) . . . . ?
C8 N10 C11 O12 180.0 . . . . ?
C13 N10 C11 O12 0.000(1) . . . . ?
C8 N10 C11 C7 0.0 . . . . ?
C13 N10 C11 C7 180.0 . . . . ?
C2 C7 C11 O12 0.000(1) . . . . ?
C6 C7 C11 O12 180.0 . . . . ?
C2 C7 C11 N10 180.0 . . . . ?
C6 C7 C11 N10 0.0 . . . . ?
C11 N10 C13 C14 -62.4(2) . . . . ?
C8 N10 C13 C14 117.6(2) . . . . ?
C11 N10 C13 C14 62.4(2) . . . 3 ?
C8 N10 C13 C14 -117.6(2) . . . 3 ?
N10 C13 C14 C15 -179.3(2) . . . . ?
C14 C13 C14 C15 56.1(4) 3 . . . ?
C13 C14 C15 C16 -56.2(3) . . . . ?
C14 C15 C16 C15 56.5(4) . . . 3 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1420249'
_audit_update_record             
;
2015-08-24 deposited with the CCDC.
2015-10-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3,6-Dihydroxy-N-cyclohexylphthalimide
_chemical_name_common            DHNHPI
_chemical_formula_moiety         'C14 H15 N O4'
_chemical_formula_sum            'C14 H15 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       platelet
_exptl_crystal_colour            Yellow

_diffrn_ambient_temperature      173(2)
_diffrn_ambient_pressure         101.3
_chemical_formula_weight         261.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_int_tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_chemical_absolute_configuration .

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.09090(10)
_cell_length_b                   5.20710(10)
_cell_length_c                   23.0054(4)
_cell_angle_alpha                93.8260(10)
_cell_angle_beta                 94.8570(10)
_cell_angle_gamma                98.1020(10)
_cell_volume                     599.675(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7110
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      68.22
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   'abscore, T.Higashi, RIGAKU'

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'rotating anode x-ray'
_diffrn_source_type              RIGAKU
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'RIGAKU R-AXIS RAPID-2'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 10.0
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7110
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         68.22
_reflns_number_total             2142
_reflns_number_gt                1790
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       RAPID-AUTO
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        RAPID-AUTO
_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 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)+(0.0655P)²+0.1832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2142
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1339
_refine_ls_goodness_of_fit_ref   1.212
_refine_ls_restrained_S_all      1.212
_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
C1 C 1.4090(4) -0.5414(4) 0.21463(8) 0.0254(5) Uani 1 1 d . . .
C2 C 1.3109(4) -0.4430(4) 0.15899(8) 0.0253(5) Uani 1 1 d . . .
C3 C 1.3670(4) -0.4882(4) 0.10159(8) 0.0269(5) Uani 1 1 d . . .
C4 C 1.2374(5) -0.3529(4) 0.05920(9) 0.0321(5) Uani 1 1 d . . .
C5 C 1.0640(5) -0.1834(4) 0.07369(9) 0.0323(5) Uani 1 1 d . . .
C6 C 1.0084(4) -0.1387(4) 0.13184(8) 0.0263(5) Uani 1 1 d . . .
C7 C 1.1351(4) -0.2700(4) 0.17285(8) 0.0248(4) Uani 1 1 d . . .
C8 C 1.1163(4) -0.2566(4) 0.23615(8) 0.0247(5) Uani 1 1 d . . .
C9 C 1.3423(4) -0.4513(4) 0.32199(8) 0.0241(4) Uani 1 1 d . . .
C10 C 1.4730(4) -0.1927(4) 0.35425(9) 0.0267(5) Uani 1 1 d . . .
C11 C 1.5341(4) -0.2239(4) 0.41945(9) 0.0298(5) Uani 1 1 d . . .
C12 C 1.2841(4) -0.3341(4) 0.44684(9) 0.0288(5) Uani 1 1 d . . .
C13 C 1.1574(5) -0.5920(4) 0.41439(9) 0.0289(5) Uani 1 1 d . . .
C14 C 1.0918(4) -0.5634(4) 0.34925(9) 0.0268(5) Uani 1 1 d . . .
N1 N 1.2839(3) -0.4205(3) 0.25905(7) 0.0252(4) Uani 1 1 d . . .
O1 O 1.5641(3) -0.6953(3) 0.22273(6) 0.0333(4) Uani 1 1 d . . .
O2 O 1.5327(3) -0.6500(3) 0.08240(6) 0.0342(4) Uani 1 1 d . . .
O3 O 0.8381(3) 0.0316(3) 0.14563(7) 0.0337(4) Uani 1 1 d . . .
O4 O 0.9793(3) -0.1247(3) 0.26324(6) 0.0303(4) Uani 1 1 d . . .
H2 H 1.614(7) -0.731(7) 0.1093(15) 0.078(11) Uiso 1 1 d . . .
H3 H 0.821(7) 0.037(7) 0.1853(16) 0.086(11) Uiso 1 1 d . . .
H4 H 1.283(5) -0.381(5) 0.0182(12) 0.049(7) Uiso 1 1 d . . .
H5 H 0.968(5) -0.091(5) 0.0433(11) 0.043(7) Uiso 1 1 d . . .
H9 H 1.473(4) -0.577(4) 0.3223(8) 0.020(5) Uiso 1 1 d . . .
H10A H 1.633(5) -0.136(4) 0.3367(10) 0.036(6) Uiso 1 1 d . . .
H10B H 1.347(5) -0.064(4) 0.3492(10) 0.033(6) Uiso 1 1 d . . .
H11A H 1.671(5) -0.343(4) 0.4247(10) 0.031(6) Uiso 1 1 d . . .
H11B H 1.624(5) -0.048(5) 0.4406(10) 0.037(6) Uiso 1 1 d . . .
H12A H 1.335(4) -0.357(4) 0.4890(10) 0.029(6) Uiso 1 1 d . . .
H12B H 1.153(4) -0.204(4) 0.4459(9) 0.027(5) Uiso 1 1 d . . .
H13A H 1.285(5) -0.723(4) 0.4187(10) 0.034(6) Uiso 1 1 d . . .
H13B H 0.994(5) -0.659(4) 0.4313(10) 0.033(6) Uiso 1 1 d . . .
H14A H 1.012(4) -0.734(4) 0.3277(9) 0.032(6) Uiso 1 1 d . . .
H14B H 0.959(4) -0.445(4) 0.3443(9) 0.031(6) Uiso 1 1 d . . .


_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
C1 O1 1.214(2) . ?
C1 N1 1.408(2) . ?
C1 C2 1.484(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.397(3) . ?
C3 O2 1.353(2) . ?
C3 C4 1.413(3) . ?
C4 C5 1.378(3) . ?
C4 H4 1.00(3) . ?
C5 C6 1.402(3) . ?
C5 H5 1.01(3) . ?
C6 O3 1.365(2) . ?
C6 C7 1.372(3) . ?
C7 C8 1.465(3) . ?
C8 O4 1.224(2) . ?
C8 N1 1.387(2) . ?
C9 N1 1.477(2) . ?
C9 C14 1.528(3) . ?
C9 C10 1.529(3) . ?
C9 H9 1.00(2) . ?
C10 C11 1.530(3) . ?
C10 H10A 0.96(2) . ?
C10 H10B 1.00(2) . ?
C11 C12 1.525(3) . ?
C11 H11A 1.00(2) . ?
C11 H11B 1.04(2) . ?
C12 C13 1.522(3) . ?
C12 H12A 1.00(2) . ?
C12 H12B 1.02(2) . ?
C13 C14 1.529(3) . ?
C13 H13A 1.01(2) . ?
C13 H13B 0.98(2) . ?
C14 H14A 1.00(2) . ?
C14 H14B 0.98(2) . ?
O2 H2 0.88(4) . ?
O3 H3 0.92(4) . ?

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
O1 C1 N1 124.57(18) . . ?
O1 C1 C2 129.18(18) . . ?
N1 C1 C2 106.25(16) . . ?
C3 C2 C7 120.32(18) . . ?
C3 C2 C1 132.52(19) . . ?
C7 C2 C1 107.14(16) . . ?
O2 C3 C2 126.20(18) . . ?
O2 C3 C4 117.10(18) . . ?
C2 C3 C4 116.70(19) . . ?
C5 C4 C3 122.16(19) . . ?
C5 C4 H4 121.4(15) . . ?
C3 C4 H4 116.4(15) . . ?
C4 C5 C6 120.80(19) . . ?
C4 C5 H5 122.1(14) . . ?
C6 C5 H5 117.0(14) . . ?
O3 C6 C7 122.99(18) . . ?
O3 C6 C5 120.16(18) . . ?
C7 C6 C5 116.84(19) . . ?
C6 C7 C2 123.19(18) . . ?
C6 C7 C8 128.06(18) . . ?
C2 C7 C8 108.75(17) . . ?
O4 C8 N1 127.02(18) . . ?
O4 C8 C7 126.23(18) . . ?
N1 C8 C7 106.75(16) . . ?
N1 C9 C14 111.36(16) . . ?
N1 C9 C10 110.54(15) . . ?
C14 C9 C10 111.46(16) . . ?
N1 C9 H9 103.3(11) . . ?
C14 C9 H9 110.4(11) . . ?
C10 C9 H9 109.5(11) . . ?
C9 C10 C11 110.72(17) . . ?
C9 C10 H10A 108.0(14) . . ?
C11 C10 H10A 110.8(14) . . ?
C9 C10 H10B 108.1(13) . . ?
C11 C10 H10B 109.6(13) . . ?
H10A C10 H10B 109.6(19) . . ?
C12 C11 C10 111.31(17) . . ?
C12 C11 H11A 109.2(13) . . ?
C10 C11 H11A 109.6(13) . . ?
C12 C11 H11B 112.0(13) . . ?
C10 C11 H11B 109.8(13) . . ?
H11A C11 H11B 104.8(18) . . ?
C13 C12 C11 110.43(17) . . ?
C13 C12 H12A 110.9(12) . . ?
C11 C12 H12A 108.3(12) . . ?
C13 C12 H12B 110.4(12) . . ?
C11 C12 H12B 109.6(12) . . ?
H12A C12 H12B 107.1(16) . . ?
C12 C13 C14 111.51(17) . . ?
C12 C13 H13A 109.3(13) . . ?
C14 C13 H13A 108.7(13) . . ?
C12 C13 H13B 110.1(13) . . ?
C14 C13 H13B 109.2(13) . . ?
H13A C13 H13B 107.9(18) . . ?
C9 C14 C13 110.31(17) . . ?
C9 C14 H14A 109.7(13) . . ?
C13 C14 H14A 111.6(13) . . ?
C9 C14 H14B 108.6(13) . . ?
C13 C14 H14B 109.6(13) . . ?
H14A C14 H14B 106.9(17) . . ?
C8 N1 C1 111.12(16) . . ?
C8 N1 C9 125.13(15) . . ?
C1 N1 C9 123.60(15) . . ?
C3 O2 H2 116(2) . . ?
C6 O3 H3 109(2) . . ?

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
O1 C1 C2 C3 -1.7(4) . . . . ?
N1 C1 C2 C3 178.6(2) . . . . ?
O1 C1 C2 C7 179.9(2) . . . . ?
N1 C1 C2 C7 0.2(2) . . . . ?
C7 C2 C3 O2 179.98(18) . . . . ?
C1 C2 C3 O2 1.7(4) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C4 -178.6(2) . . . . ?
O2 C3 C4 C5 179.89(19) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 O3 179.39(18) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
O3 C6 C7 C2 -179.54(18) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
O3 C6 C7 C8 0.0(3) . . . . ?
C5 C6 C7 C8 179.06(19) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C1 C2 C7 C6 179.14(18) . . . . ?
C3 C2 C7 C8 -179.10(17) . . . . ?
C1 C2 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 O4 0.7(3) . . . . ?
C2 C7 C8 O4 -179.70(19) . . . . ?
C6 C7 C8 N1 -178.97(19) . . . . ?
C2 C7 C8 N1 0.6(2) . . . . ?
N1 C9 C10 C11 -179.94(15) . . . . ?
C14 C9 C10 C11 55.6(2) . . . . ?
C9 C10 C11 C12 -55.9(2) . . . . ?
C10 C11 C12 C13 56.4(2) . . . . ?
C11 C12 C13 C14 -56.9(2) . . . . ?
N1 C9 C14 C13 -179.72(15) . . . . ?
C10 C9 C14 C13 -55.8(2) . . . . ?
C12 C13 C14 C9 56.5(2) . . . . ?
O4 C8 N1 C1 179.80(19) . . . . ?
C7 C8 N1 C1 -0.5(2) . . . . ?
O4 C8 N1 C9 -4.6(3) . . . . ?
C7 C8 N1 C9 175.09(16) . . . . ?
O1 C1 N1 C8 -179.50(19) . . . . ?
C2 C1 N1 C8 0.2(2) . . . . ?
O1 C1 N1 C9 4.8(3) . . . . ?
C2 C1 N1 C9 -175.45(16) . . . . ?
C14 C9 N1 C8 63.5(2) . . . . ?
C10 C9 N1 C8 -61.0(2) . . . . ?
C14 C9 N1 C1 -121.42(19) . . . . ?
C10 C9 N1 C1 114.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        68.22
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.051

