# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_bmabaome
_database_code_depnum_ccdc_archive 'CCDC 1057300'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H24 N2 O5'
_chemical_formula_sum            'C17 H24 N2 O5'
_chemical_formula_weight         336.38
_chemical_melting_point          ?
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'

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_cell_length_a                   12.8074(9)
_cell_length_b                   14.8520(6)
_cell_length_c                   10.0676(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.024(7)
_cell_angle_gamma                90.00
_cell_volume                     1787.53(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.184
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_sigmaI/netI    0.0536
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7017
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         1.70
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 28.28
_diffrn_measured_fraction_theta_max 28.28
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3236
_reflns_number_total             3935
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    ?
_computing_publication_material  ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.4
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3935
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0827
_refine_ls_R_factor_gt           0.0679
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0542P)²+2.2117P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1616
_refine_ls_wR_factor_ref         0.1688
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
O3 O 0.40002(14) 0.22822(11) 0.34181(17) 0.0204(4) Uani 1 1 d . . .
O1 O 0.10568(14) 0.58347(12) 0.46871(18) 0.0232(4) Uani 1 1 d . . .
O2 O 0.06245(15) 0.61644(12) 0.23358(18) 0.0259(4) Uani 1 1 d . . .
O5 O 0.48735(15) 0.01412(12) 0.31183(19) 0.0256(4) Uani 1 1 d . . .
O4 O 0.33240(16) 0.05181(13) 0.13038(19) 0.0298(4) Uani 1 1 d . . .
N1 N 0.17848(17) 0.50029(14) 0.3453(2) 0.0201(4) Uani 1 1 d . . .
H17 H 0.2104 0.4770 0.4283 0.024 Uiso 1 1 calc R . .
C10 C 0.30454(18) 0.33954(15) 0.1700(2) 0.0158(5) Uani 1 1 d . . .
N2 N 0.42672(17) 0.22315(13) 0.1344(2) 0.0201(4) Uani 1 1 d . . .
H8 H 0.4152 0.2457 0.0517 0.024 Uiso 1 1 calc R . .
C6 C 0.20316(18) 0.45964(16) 0.2341(2) 0.0174(5) Uani 1 1 d . . .
C8 C 0.1958(2) 0.44470(18) -0.0063(3) 0.0246(5) Uani 1 1 d . . .
H5 H 0.1691 0.4647 -0.1000 0.030 Uiso 1 1 calc R . .
C12 C 0.37945(19) 0.25955(15) 0.2213(2) 0.0169(5) Uani 1 1 d . . .
C11 C 0.27131(18) 0.38387(15) 0.2701(2) 0.0162(5) Uani 1 1 d . . .
H2 H 0.2952 0.3624 0.3630 0.019 Uiso 1 1 calc R . .
C5 C 0.11020(19) 0.57204(16) 0.3384(3) 0.0194(5) Uani 1 1 d . . .
C9 C 0.2660(2) 0.37028(16) 0.0293(3) 0.0215(5) Uani 1 1 d . . .
H6 H 0.2870 0.3414 -0.0392 0.026 Uiso 1 1 calc R . .
C4 C 0.0392(2) 0.65698(17) 0.4977(3) 0.0246(5) Uani 1 1 d . . .
C7 C 0.1643(2) 0.49013(17) 0.0938(3) 0.0219(5) Uani 1 1 d . . .
H4 H 0.1179 0.5403 0.0677 0.026 Uiso 1 1 calc R . .
C16 C 0.4276(2) 0.06638(16) 0.2039(2) 0.0203(5) Uani 1 1 d . . .
C13 C 0.4980(2) 0.14453(17) 0.1838(3) 0.0247(5) Uani 1 1 d . . .
H9 H 0.5544 0.1590 0.2769 0.030 Uiso 1 1 calc R . .
C14 C 0.5586(2) 0.11928(19) 0.0848(3) 0.0309(6) Uani 1 1 d . . .
H14a H 0.5042 0.1115 -0.0106 0.037 Uiso 1 1 calc R . .
H14b H 0.5963 0.0621 0.1149 0.037 Uiso 1 1 calc R . .
C17 C 0.4293(3) -0.06363(18) 0.3380(3) 0.0335(6) Uani 1 1 d . . .
H12a H 0.4058 -0.1016 0.2554 0.050 Uiso 1 1 calc R . .
H12b H 0.3650 -0.0442 0.3581 0.050 Uiso 1 1 calc R . .
H12c H 0.4786 -0.0966 0.4179 0.050 Uiso 1 1 calc R . .
C3 C -0.0823(2) 0.6508(2) 0.3986(3) 0.0365(7) Uani 1 1 d . . .
H21a H -0.0886 0.6692 0.3046 0.055 Uiso 1 1 calc R . .
H21b H -0.1273 0.6896 0.4326 0.055 Uiso 1 1 calc R . .
H21c H -0.1079 0.5899 0.3959 0.055 Uiso 1 1 calc R . .
C15 C 0.6441(2) 0.1893(2) 0.0812(4) 0.0382(7) Uani 1 1 d . . .
H15a H 0.6824 0.1687 0.0207 0.057 Uiso 1 1 calc R . .
H15b H 0.6971 0.1985 0.1757 0.057 Uiso 1 1 calc R . .
H15c H 0.6066 0.2450 0.0449 0.057 Uiso 1 1 calc R . .
C1 C 0.0498(2) 0.6374(2) 0.6497(3) 0.0321(6) Uani 1 1 d . . .
H22a H 0.0209 0.5784 0.6548 0.048 Uiso 1 1 calc R . .
H22b H 0.0080 0.6813 0.6800 0.048 Uiso 1 1 calc R . .
H22c H 0.1271 0.6402 0.7104 0.048 Uiso 1 1 calc R . .
C2 C 0.0933(3) 0.74662(19) 0.4888(3) 0.0378(7) Uani 1 1 d . . .
H23a H 0.1683 0.7478 0.5571 0.057 Uiso 1 1 calc R . .
H23b H 0.0508 0.7946 0.5087 0.057 Uiso 1 1 calc R . .
H23c H 0.0951 0.7542 0.3949 0.057 Uiso 1 1 calc R . .


_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
O3 C12 1.236(3) . ?
O1 C5 1.345(3) . ?
O1 C4 1.476(3) . ?
O2 C5 1.208(3) . ?
O5 C16 1.331(3) . ?
O5 C17 1.448(3) . ?
O4 C16 1.197(3) . ?
N1 C6 1.404(3) . ?
N1 C5 1.364(3) . ?
C10 C12 1.498(3) . ?
C10 C11 1.392(3) . ?
C10 C9 1.399(3) . ?
N2 C12 1.344(3) . ?
N2 C13 1.455(3) . ?
C6 C11 1.390(3) . ?
C6 C7 1.394(3) . ?
C8 C9 1.388(3) . ?
C8 C7 1.388(3) . ?
C4 C3 1.521(4) . ?
C4 C1 1.515(4) . ?
C4 C2 1.518(4) . ?
C16 C13 1.527(3) . ?
C13 C14 1.514(3) . ?
C14 C15 1.520(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
C5 O1 C4 121.07(19) . . ?
C16 O5 C17 115.6(2) . . ?
C5 N1 C6 128.2(2) . . ?
C11 C10 C12 116.7(2) . . ?
C11 C10 C9 119.3(2) . . ?
C9 C10 C12 123.9(2) . . ?
C12 N2 C13 118.3(2) . . ?
C11 C6 N1 116.1(2) . . ?
C11 C6 C7 119.3(2) . . ?
C7 C6 N1 124.6(2) . . ?
C7 C8 C9 122.0(2) . . ?
O3 C12 C10 121.5(2) . . ?
O3 C12 N2 120.0(2) . . ?
N2 C12 C10 118.5(2) . . ?
C6 C11 C10 121.4(2) . . ?
O1 C5 N1 107.4(2) . . ?
O2 C5 O1 126.7(2) . . ?
O2 C5 N1 125.8(2) . . ?
C8 C9 C10 118.8(2) . . ?
O1 C4 C3 110.7(2) . . ?
O1 C4 C1 102.1(2) . . ?
O1 C4 C2 109.2(2) . . ?
C1 C4 C3 110.5(2) . . ?
C1 C4 C2 110.5(2) . . ?
C2 C4 C3 113.3(2) . . ?
C8 C7 C6 119.1(2) . . ?
O5 C16 C13 111.0(2) . . ?
O4 C16 O5 124.0(2) . . ?
O4 C16 C13 125.0(2) . . ?
N2 C13 C16 109.12(19) . . ?
N2 C13 C14 112.4(2) . . ?
C14 C13 C16 111.5(2) . . ?
C13 C14 C15 112.9(2) . . ?

####################################################################### 
# 
# 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_dh_rs_02
_database_code_depnum_ccdc_archive 'CCDC 1057301'
_audit_update_record             
;
2015-04-01 deposited with the CCDC.
2015-07-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 N2 O5'
_chemical_formula_weight         266.25

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           Orthorhombic
_symmetry_space_group_name_H-M   Pca21

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

_cell_length_a                   13.8537(16)
_cell_length_b                   4.8506(4)
_cell_length_c                   18.6706(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1254.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      26.980

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.442
_exptl_crystal_size_mid          0.224
_exptl_crystal_size_min          0.126
_exptl_crystal_density_meas      1.410
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560.0
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3426
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.94
_diffrn_reflns_theta_max         26.98
_reflns_number_total             2007
_reflns_number_gt                1621
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0819P)²+1.1295P] 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   0.1(3)
_refine_ls_number_reflns         2007
_refine_ls_number_parameters     174
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1945
_refine_ls_wR_factor_gt          0.1747
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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
O5 O 0.2687(2) 0.2945(7) 0.3986(2) 0.0338(8) Uani 1 1 d . . .
O3 O 0.2190(3) -0.0254(7) 0.2597(2) 0.0385(9) Uani 1 1 d . . .
C1 C 0.3348(4) 0.1579(14) 0.4467(3) 0.0416(13) Uani 1 1 d . . .
H1A H 0.3140 0.1851 0.4953 0.062 Uiso 1 1 calc R . .
H1B H 0.3984 0.2336 0.4407 0.062 Uiso 1 1 calc R . .
H1C H 0.3362 -0.0358 0.4362 0.062 Uiso 1 1 calc R . .
C2 C 0.1810(4) 0.1870(10) 0.3968(3) 0.0293(10) Uani 1 1 d . . .
C3 C 0.1173(4) 0.3559(15) 0.3447(3) 0.0435(15) Uani 1 1 d . . .
H3 H 0.1058 0.5347 0.3675 0.052 Uiso 1 1 calc R . .
N2 N 0.1680(3) 0.4109(9) 0.2789(2) 0.0320(10) Uani 1 1 d . . .
H4 H 0.1675 0.5771 0.2629 0.038 Uiso 1 1 calc R . .
C4 C 0.2156(3) 0.2204(10) 0.2413(3) 0.0270(11) Uani 1 1 d . . .
C5 C 0.2683(3) 0.3169(10) 0.1756(2) 0.0247(10) Uani 1 1 d . . .
C6 C 0.3555(3) 0.1908(10) 0.1582(3) 0.0270(10) Uani 1 1 d . . .
H6 H 0.3794 0.0457 0.1855 0.032 Uiso 1 1 calc R . .
C7 C 0.4052(4) 0.2866(11) 0.0996(3) 0.0309(11) Uani 1 1 d . . .
N1 N 0.4978(3) 0.1637(12) 0.0829(3) 0.0452(13) Uani 1 1 d . . .
O2 O 0.5432(3) 0.2545(11) 0.0312(2) 0.0591(14) Uani 1 1 d . . .
C11 C 0.0217(4) 0.2246(14) 0.3354(3) 0.0467(14) Uani 1 1 d . . .
H11A H -0.0066 0.1895 0.3820 0.056 Uiso 1 1 calc R . .
H11B H 0.0295 0.0491 0.3111 0.056 Uiso 1 1 calc R . .
C12 C -0.0465(4) 0.4112(14) 0.2913(3) 0.0476(15) Uani 1 1 d . . .
H12A H -0.0584 0.5789 0.3171 0.071 Uiso 1 1 calc R . .
H12B H -0.1065 0.3169 0.2833 0.071 Uiso 1 1 calc R . .
H12C H -0.0171 0.4535 0.2460 0.071 Uiso 1 1 calc R . .
C10 C 0.2327(3) 0.5290(10) 0.1333(2) 0.0275(10) Uani 1 1 d . . .
H10 H 0.1744 0.6126 0.1450 0.033 Uiso 1 1 calc R . .
C9 C 0.2837(4) 0.6164(11) 0.0739(3) 0.0315(11) Uani 1 1 d . . .
H9 H 0.2585 0.7546 0.0448 0.038 Uiso 1 1 calc R . .
C8 C 0.3723(4) 0.4987(12) 0.0573(3) 0.0330(12) Uani 1 1 d . . .
H8 H 0.4085 0.5619 0.0187 0.040 Uiso 1 1 calc R . .
O1 O 0.5286(3) -0.0230(11) 0.1217(3) 0.0622(14) Uani 1 1 d . . .
O4 O 0.1530(3) 0.0026(7) 0.43432(18) 0.0328(8) Uani 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
O5 C2 1.322(6) . ?
O5 C1 1.445(6) . ?
O3 C4 1.242(6) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O4 1.200(6) . ?
C2 C3 1.549(7) . ?
C3 N2 1.439(6) . ?
C3 C11 1.479(8) . ?
C3 H3 0.9800 . ?
N2 C4 1.336(6) . ?
N2 H4 0.8600 . ?
C4 C5 1.501(6) . ?
C5 C10 1.388(6) . ?
C5 C6 1.392(6) . ?
C6 C7 1.374(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(8) . ?
C7 N1 1.449(7) . ?
N1 O2 1.233(7) . ?
N1 O1 1.235(7) . ?
C11 C12 1.546(8) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 C9 1.382(7) . ?
C10 H10 0.9300 . ?
C9 C8 1.389(8) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?

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 O5 C1 114.7(4) . . ?
O5 C1 H1A 109.5 . . ?
O5 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O5 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C2 O5 125.2(5) . . ?
O4 C2 C3 125.2(5) . . ?
O5 C2 C3 109.3(4) . . ?
N2 C3 C11 114.6(5) . . ?
N2 C3 C2 110.9(4) . . ?
C11 C3 C2 110.9(5) . . ?
N2 C3 H3 106.7 . . ?
C11 C3 H3 106.7 . . ?
C2 C3 H3 106.7 . . ?
C4 N2 C3 124.2(5) . . ?
C4 N2 H4 117.9 . . ?
C3 N2 H4 117.9 . . ?
O3 C4 N2 122.5(4) . . ?
O3 C4 C5 120.5(5) . . ?
N2 C4 C5 117.0(4) . . ?
C10 C5 C6 120.1(4) . . ?
C10 C5 C4 121.5(4) . . ?
C6 C5 C4 118.4(4) . . ?
C7 C6 C5 118.2(5) . . ?
C7 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C8 C7 C6 123.0(5) . . ?
C8 C7 N1 118.6(5) . . ?
C6 C7 N1 118.4(5) . . ?
O2 N1 O1 123.0(5) . . ?
O2 N1 C7 118.2(5) . . ?
O1 N1 C7 118.8(5) . . ?
C3 C11 C12 111.0(5) . . ?
C3 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C3 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C10 C5 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C5 C10 H10 119.9 . . ?
C10 C9 C8 120.3(5) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C7 C8 C9 118.3(5) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 H8 120.9 . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        26.98
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.069
