# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_AGSM_1_a
_database_code_depnum_ccdc_archive 'CCDC 1018133'
_audit_update_record             
;
2014-08-05 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014

_chemical_name_systematic        
;
 ?

;
_chemical_name_common            ?

_chemical_melting_point          ?
_chemical_formula_moiety         ?

_chemical_formula_sum            'C18 H14 N2 O2'

_chemical_formula_weight         290.31



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'


_space_group_crystal_system      monoclinic

_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'

_space_group_name_Hall           '-P 2ybc'


_shelx_space_group_comment       
;

The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of

symmetry information in preference to the above space-group names.
They are only intended as comments.

;


loop_
_space_group_symop_operation_xyz


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


_cell_length_a                   5.9644(5)

_cell_length_b                   14.7386(12)
_cell_length_c                   16.5422(13)

_cell_angle_alpha                90
_cell_angle_beta                 92.149(6)

_cell_angle_gamma                90
_cell_volume                     1453.2(2)

_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)

_cell_measurement_reflns_used    2939
_cell_measurement_theta_min      2.83

_cell_measurement_theta_max      21.02


_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Orange

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?

_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             608

_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.10

_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.088

_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_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      296(2)

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'

_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            26550
_diffrn_reflns_av_unetI/netI     0.0353

_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_limit_h_min       -7

_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17

_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21

_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.851

_diffrn_reflns_theta_max         28.421
_diffrn_reflns_theta_full        25.242

_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998

_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998

_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998

_reflns_number_total             3611
_reflns_number_gt                1849

_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000

_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal

 class for the calculation of statistics and refinement.
 

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be

 possible theoretically, ignoring centric projections and
 systematic absences.

;


_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'

_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;

 ?
;
_refine_ls_structure_factor_coef Fsqd

_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc

_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .

_refine_ls_number_reflns         3611
_refine_ls_number_parameters     201

_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1137

_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1925

_refine_ls_wR_factor_gt          0.1493
_refine_ls_goodness_of_fit_ref   1.036

_refine_ls_restrained_S_all      1.036
_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_site_symmetry_order

_atom_site_calc_flag
_atom_site_refinement_flags_posn

_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy

_atom_site_disorder_assembly
_atom_site_disorder_group


















O001 O 1.5971(2) 0.58452(10) 0.66367(8) 0.0804(5) Uani 1 1 d . . . . .
H001 H 1.6301 0.6003 0.7101 0.121 Uiso 1 1 calc R U . . .
N002 N 0.7328(2) 0.33764(10) 0.59920(9) 0.0578(4) Uani 1 1 d . . . . .
N003 N 0.5599(2) 0.27647(10) 0.61026(9) 0.0586(4) Uani 1 1 d . . . . .
O004 O 0.3516(3) 0.15537(11) 0.68596(10) 0.0889(5) Uani 1 1 d . . . . .
H004 H 0.4559 0.1888 0.6748 0.133 Uiso 1 1 calc R U . . .
C005 C 1.0642(3) 0.40305(11) 0.66042(10) 0.0516(4) Uani 1 1 d . . . . .
C006 C 0.2255(3) 0.20749(12) 0.55548(11) 0.0570(5) Uani 1 1 d . . . . .
C007 C 0.4098(3) 0.26828(12) 0.55162(11) 0.0556(5) Uani 1 1 d . . . . .
H007 H 0.4236 0.3035 0.5054 0.067 Uiso 1 1 calc R U . . .
C008 C 1.4262(3) 0.52363(13) 0.66435(11) 0.0593(5) Uani 1 1 d . . . . .
C009 C 0.0544(3) 0.20342(12) 0.49132(11) 0.0589(5) Uani 1 1 d . . . . .
C00A C 0.8732(3) 0.34293(12) 0.65968(11) 0.0576(5) Uani 1 1 d . . . . .
H00A H 0.8510 0.3067 0.7047 0.069 Uiso 1 1 calc R U . . .
C00B C 1.3751(3) 0.47467(13) 0.73302(11) 0.0628(5) Uani 1 1 d . . . . .
H00B H 1.4611 0.4820 0.7806 0.075 Uiso 1 1 calc R U . . .
C00C C 1.1969(3) 0.41535(13) 0.73036(11) 0.0610(5) Uani 1 1 d . . . . .
H00C H 1.1645 0.3827 0.7766 0.073 Uiso 1 1 calc R U . . .
C00D C 1.1235(3) 0.45095(13) 0.59151(11) 0.0616(5) Uani 1 1 d . . . . .
H00D H 1.0410 0.4424 0.5433 0.074 Uiso 1 1 calc R U . . .
C00E C 0.2072(3) 0.15125(14) 0.62425(14) 0.0700(6) Uani 1 1 d . . . . .
C00F C 0.0481(4) 0.26322(14) 0.42414(12) 0.0689(6) Uani 1 1 d . . . . .
H00F H 0.1635 0.3049 0.4187 0.083 Uiso 1 1 calc R U . . .
C00G C -0.1235(3) 0.14072(14) 0.49641(13) 0.0696(6) Uani 1 1 d . . . . .
C00H C 1.2999(3) 0.50989(13) 0.59348(11) 0.0652(5) Uani 1 1 d . . . . .
H00H H 1.3356 0.5411 0.5468 0.078 Uiso 1 1 calc R U . . .
C00I C -0.1240(4) 0.26094(16) 0.36714(13) 0.0792(6) Uani 1 1 d . . . . .
H00I H -0.1251 0.3017 0.3242 0.095 Uiso 1 1 calc R U . . .
C00J C -0.2944(4) 0.13946(18) 0.43516(16) 0.0866(7) Uani 1 1 d . . . . .
H00J H -0.4088 0.0968 0.4379 0.104 Uiso 1 1 calc R U . . .
C00K C -0.1277(4) 0.08358(16) 0.56545(17) 0.0902(8) Uani 1 1 d . . . . .
H00K H -0.2420 0.0410 0.5685 0.108 Uiso 1 1 calc R U . . .
C00L C 0.0273(4) 0.08866(16) 0.62669(17) 0.0893(7) Uani 1 1 d . . . . .
H00L H 0.0160 0.0505 0.6712 0.107 Uiso 1 1 calc R U . . .
C00M C -0.2968(4) 0.1986(2) 0.37250(15) 0.0902(8) Uani 1 1 d . . . . .
H00M H -0.4131 0.1975 0.3335 0.108 Uiso 1 1 calc R U . . .




_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












O001 C008 1.358(2) . ?
N002 C00A 1.283(2) . ?
N002 N003 1.387(2) . ?
N003 C007 1.301(2) . ?
O004 C00E 1.312(2) . ?
C005 C00C 1.389(2) . ?
C005 C00D 1.398(2) . ?
C005 C00A 1.443(2) . ?
C006 C00E 1.415(3) . ?
C006 C007 1.421(2) . ?
C006 C009 1.446(2) . ?
C008 C00H 1.385(2) . ?
C008 C00B 1.389(3) . ?
C009 C00G 1.412(3) . ?
C009 C00F 1.418(3) . ?
C00B C00C 1.376(3) . ?
C00D C00H 1.364(3) . ?
C00E C00L 1.417(3) . ?
C00F C00I 1.368(3) . ?
C00G C00J 1.410(3) . ?
C00G C00K 1.420(3) . ?
C00I C00M 1.385(3) . ?
C00J C00M 1.354(3) . ?
C00K C00L 1.348(3) . ?


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
















C00A N002 N003 113.80(15) . . ?
C007 N003 N002 117.16(15) . . ?
C00C C005 C00D 117.37(17) . . ?
C00C C005 C00A 120.81(16) . . ?
C00D C005 C00A 121.81(16) . . ?
C00E C006 C007 119.24(18) . . ?
C00E C006 C009 119.48(18) . . ?
C007 C006 C009 121.27(17) . . ?
N003 C007 C006 122.47(17) . . ?
O001 C008 C00H 118.31(17) . . ?
O001 C008 C00B 122.52(17) . . ?
C00H C008 C00B 119.17(18) . . ?
C00G C009 C00F 117.11(19) . . ?
C00G C009 C006 119.66(18) . . ?
C00F C009 C006 123.15(17) . . ?
N002 C00A C005 122.41(16) . . ?
C00C C00B C008 119.79(17) . . ?
C00B C00C C005 121.67(17) . . ?
C00H C00D C005 121.39(17) . . ?
O004 C00E C006 122.02(18) . . ?
O004 C00E C00L 118.9(2) . . ?
C006 C00E C00L 119.1(2) . . ?
C00I C00F C009 121.5(2) . . ?
C00J C00G C009 119.4(2) . . ?
C00J C00G C00K 122.4(2) . . ?
C009 C00G C00K 118.2(2) . . ?
C00D C00H C008 120.54(17) . . ?
C00F C00I C00M 120.8(2) . . ?
C00M C00J C00G 121.9(2) . . ?
C00L C00K C00G 122.6(2) . . ?
C00K C00L C00E 120.9(2) . . ?
C00J C00M C00I 119.3(2) . . ?


_refine_diff_density_max         0.239
_refine_diff_density_min         -0.156

_refine_diff_density_rms         0.038







####################################################################### 
# 
# 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_HYHNNO2_1_a
_database_code_depnum_ccdc_archive 'CCDC 1415557'
_audit_update_record             
;
2015-07-28 deposited with the CCDC.
2015-11-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N3 O3'
_chemical_formula_weight         319.31

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2028(3)
_cell_length_b                   7.9197(3)
_cell_length_c                   14.7696(6)
_cell_angle_alpha                81.753(3)
_cell_angle_beta                 84.845(2)
_cell_angle_gamma                65.428(2)
_cell_volume                     757.87(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2048
_cell_measurement_theta_min      3.31
_cell_measurement_theta_max      25.57

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_F_000             332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11866
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0331
_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       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         26.292
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3048
_reflns_number_gt                1830
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0816P)²+0.0025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.027(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8613(2) 0.00836(17) 0.40921(8) 0.0681(4) Uani 1 1 d . . . . .
H1 H 0.8409 0.0992 0.4355 0.102 Uiso 1 1 calc R U . . .
N002 N 0.7861(2) 0.34934(18) 0.42395(9) 0.0519(4) Uani 1 1 d . . . . .
N003 N 0.7516(2) 0.50629(19) 0.46776(9) 0.0540(4) Uani 1 1 d . . . . .
O3 O 0.6185(3) 1.1837(2) 0.74725(11) 0.0950(5) Uani 1 1 d . . . . .
N1 N 0.6513(2) 1.0248(2) 0.78332(12) 0.0664(5) Uani 1 1 d . . . . .
O2 O 0.6621(3) 0.9798(2) 0.86551(11) 0.0985(6) Uani 1 1 d . . . . .
C007 C 0.7556(2) 0.4710(2) 0.55468(11) 0.0502(4) Uani 1 1 d . . . . .
H007 H 0.7782 0.3508 0.5816 0.060 Uiso 1 1 calc R U . . .
C008 C 0.8032(2) 0.2431(2) 0.27892(10) 0.0453(4) Uani 1 1 d . . . . .
C009 C 0.7761(2) 0.3849(2) 0.33635(11) 0.0480(4) Uani 1 1 d . . . . .
H009 H 0.7506 0.5056 0.3092 0.058 Uiso 1 1 calc R U . . .
C00A C 0.6767(2) 0.8823(2) 0.72370(11) 0.0493(4) Uani 1 1 d . . . . .
C00B C 0.7256(2) 0.6152(2) 0.61308(10) 0.0452(4) Uani 1 1 d . . . . .
C00C C 0.7896(2) 0.2856(2) 0.18092(11) 0.0498(4) Uani 1 1 d . . . . .
C00D C 0.8384(3) 0.0619(2) 0.31856(11) 0.0517(4) Uani 1 1 d . . . . .
C00E C 0.6692(3) 0.9304(2) 0.63058(12) 0.0562(5) Uani 1 1 d . . . . .
H00E H 0.6475 1.0514 0.6054 0.067 Uiso 1 1 calc R U . . .
C00F C 0.7074(3) 0.7053(2) 0.76375(11) 0.0540(5) Uani 1 1 d . . . . .
H00F H 0.7123 0.6760 0.8270 0.065 Uiso 1 1 calc R U . . .
C00G C 0.6944(3) 0.7960(2) 0.57528(11) 0.0529(5) Uani 1 1 d . . . . .
H00G H 0.6906 0.8263 0.5121 0.063 Uiso 1 1 calc R U . . .
C00H C 0.7306(3) 0.5718(2) 0.70733(11) 0.0525(5) Uani 1 1 d . . . . .
H00H H 0.7499 0.4516 0.7330 0.063 Uiso 1 1 calc R U . . .
C00I C 0.8006(3) 0.1456(3) 0.12764(12) 0.0573(5) Uani 1 1 d . . . . .
C00J C 0.8305(3) -0.0333(3) 0.17249(14) 0.0668(5) Uani 1 1 d . . . . .
H00J H 0.8370 -0.1250 0.1379 0.080 Uiso 1 1 calc R U . . .
C00K C 0.8500(3) -0.0757(3) 0.26448(13) 0.0627(5) Uani 1 1 d . . . . .
H00K H 0.8709 -0.1953 0.2919 0.075 Uiso 1 1 calc R U . . .
C00L C 0.7658(3) 0.4608(3) 0.13325(11) 0.0658(5) Uani 1 1 d . . . . .
H00L H 0.7589 0.5553 0.1660 0.079 Uiso 1 1 calc R U . . .
C00M C 0.7829(3) 0.1882(3) 0.03172(13) 0.0771(6) Uani 1 1 d . . . . .
H00M H 0.7865 0.0974 -0.0028 0.092 Uiso 1 1 calc R U . . .
C00N C 0.7529(4) 0.4948(3) 0.04085(13) 0.0868(7) Uani 1 1 d . . . . .
H00N H 0.7385 0.6114 0.0115 0.104 Uiso 1 1 calc R U . . .
C00O C 0.7610(4) 0.3572(4) -0.01089(14) 0.0932(8) Uani 1 1 d . . . . .
H00O H 0.7512 0.3821 -0.0742 0.112 Uiso 1 1 calc R U . . .


_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 C00D 1.3484(19) . ?
O1 H1 0.8200 . ?
N002 C009 1.2860(18) . ?
N002 N003 1.4037(18) . ?
N003 C007 1.2744(19) . ?
O3 N1 1.227(2) . ?
N1 O2 1.215(2) . ?
N1 C00A 1.472(2) . ?
C007 C00B 1.463(2) . ?
C007 H007 0.9300 . ?
C008 C00D 1.396(2) . ?
C008 C00C 1.441(2) . ?
C008 C009 1.443(2) . ?
C009 H009 0.9300 . ?
C00A C00E 1.373(2) . ?
C00A C00F 1.376(2) . ?
C00B C00H 1.385(2) . ?
C00B C00G 1.392(2) . ?
C00C C00L 1.412(2) . ?
C00C C00I 1.422(2) . ?
C00D C00K 1.413(2) . ?
C00E C00G 1.376(2) . ?
C00E H00E 0.9300 . ?
C00F C00H 1.386(2) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I C00J 1.413(3) . ?
C00I C00M 1.413(2) . ?
C00J C00K 1.357(2) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L C00N 1.357(2) . ?
C00L H00L 0.9300 . ?
C00M C00O 1.346(3) . ?
C00M H00M 0.9300 . ?
C00N C00O 1.398(3) . ?
C00N H00N 0.9300 . ?
C00O H00O 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
C00D O1 H1 109.5 . . ?
C009 N002 N003 113.34(13) . . ?
C007 N003 N002 112.90(14) . . ?
O2 N1 O3 123.40(16) . . ?
O2 N1 C00A 118.52(17) . . ?
O3 N1 C00A 118.07(17) . . ?
N003 C007 C00B 121.52(15) . . ?
N003 C007 H007 119.2 . . ?
C00B C007 H007 119.2 . . ?
C00D C008 C00C 118.96(14) . . ?
C00D C008 C009 119.80(14) . . ?
C00C C008 C009 121.22(15) . . ?
N002 C009 C008 121.90(15) . . ?
N002 C009 H009 119.0 . . ?
C008 C009 H009 119.0 . . ?
C00E C00A C00F 122.46(14) . . ?
C00E C00A N1 119.09(16) . . ?
C00F C00A N1 118.45(15) . . ?
C00H C00B C00G 119.21(14) . . ?
C00H C00B C007 119.87(15) . . ?
C00G C00B C007 120.91(14) . . ?
C00L C00C C00I 116.99(15) . . ?
C00L C00C C008 123.71(14) . . ?
C00I C00C C008 119.31(16) . . ?
O1 C00D C008 122.78(14) . . ?
O1 C00D C00K 116.35(16) . . ?
C008 C00D C00K 120.87(16) . . ?
C00A C00E C00G 118.71(15) . . ?
C00A C00E H00E 120.6 . . ?
C00G C00E H00E 120.6 . . ?
C00A C00F C00H 118.24(15) . . ?
C00A C00F H00F 120.9 . . ?
C00H C00F H00F 120.9 . . ?
C00E C00G C00B 120.63(15) . . ?
C00E C00G H00G 119.7 . . ?
C00B C00G H00G 119.7 . . ?
C00B C00H C00F 120.75(16) . . ?
C00B C00H H00H 119.6 . . ?
C00F C00H H00H 119.6 . . ?
C00J C00I C00M 121.86(16) . . ?
C00J C00I C00C 118.72(16) . . ?
C00M C00I C00C 119.42(18) . . ?
C00K C00J C00I 122.13(16) . . ?
C00K C00J H00J 118.9 . . ?
C00I C00J H00J 118.9 . . ?
C00J C00K C00D 119.92(18) . . ?
C00J C00K H00K 120.0 . . ?
C00D C00K H00K 120.0 . . ?
C00N C00L C00C 121.64(17) . . ?
C00N C00L H00L 119.2 . . ?
C00C C00L H00L 119.2 . . ?
C00O C00M C00I 121.54(18) . . ?
C00O C00M H00M 119.2 . . ?
C00I C00M H00M 119.2 . . ?
C00L C00N C00O 121.0(2) . . ?
C00L C00N H00N 119.5 . . ?
C00O C00N H00N 119.5 . . ?
C00M C00O C00N 119.39(19) . . ?
C00M C00O H00O 120.3 . . ?
C00N C00O H00O 120.3 . . ?

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.057
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methyl Alcohol'
