# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_SR_1
_database_code_depnum_ccdc_archive 'CCDC 1966436'
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 Cl N3 O4'
_chemical_formula_sum            'C15 H16 Cl N3 O4'
_chemical_formula_weight         337.76

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'
Cl Cl 0.1484 0.1585 '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                   8.8020(9)
_cell_length_b                   9.0045(8)
_cell_length_c                   10.8415(11)
_cell_angle_alpha                83.765(4)
_cell_angle_beta                 86.631(4)
_cell_angle_gamma                72.048(4)
_cell_volume                     812.31(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9829
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.34

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.258
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   SADABS
_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            46949
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.845
_diffrn_reflns_theta_max         27.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3732
_reflns_number_gt                3154
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0472P)²+0.2073P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.114(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3732
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0999
_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
Cl1 Cl 0.08561(7) 0.50292(7) 0.12954(4) 0.0909(2) Uani 1 1 d . . . . .
O3 O 0.54544(13) 0.26569(12) 1.02725(8) 0.0514(3) Uani 1 1 d . . . . .
O2 O 0.71468(13) 0.08971(13) 0.73977(9) 0.0565(3) Uani 1 1 d . . . . .
O4 O 0.36094(14) 0.21724(14) 0.91768(10) 0.0622(3) Uani 1 1 d . . . . .
N3 N 0.33160(15) 0.49519(13) 0.65066(10) 0.0452(3) Uani 1 1 d . . . . .
N2 N 0.31503(13) 0.45051(13) 0.53688(9) 0.0413(3) Uani 1 1 d . . . . .
O1 O 0.68259(17) 0.02486(16) 0.55229(12) 0.0832(4) Uani 1 1 d . . . . .
N1 N 0.19513(14) 0.49136(14) 0.34795(10) 0.0467(3) Uani 1 1 d . . . . .
C11 C 0.45996(16) 0.28104(14) 0.92642(11) 0.0412(3) Uani 1 1 d . . . . .
C7 C 0.51178(16) 0.26047(16) 0.61983(11) 0.0430(3) Uani 1 1 d . . . . .
C8 C 0.45100(17) 0.38044(15) 0.70096(11) 0.0426(3) Uani 1 1 d . . . . .
C1 C 0.19267(15) 0.54424(15) 0.45768(11) 0.0407(3) Uani 1 1 d . . . . .
C6 C 0.42046(16) 0.31084(16) 0.51659(12) 0.0439(3) Uani 1 1 d . . . . .
H6 H 0.429623 0.258410 0.445878 0.053 Uiso 1 1 calc R U . . .
C10 C 0.64281(17) 0.11401(18) 0.63139(13) 0.0500(3) Uani 1 1 d . . . . .
C9 C 0.5044(2) 0.39106(17) 0.82743(12) 0.0514(4) Uani 1 1 d . . . . .
H9A H 0.457553 0.497604 0.849335 0.062 Uiso 1 1 calc R U . . .
H9B H 0.619568 0.368717 0.824766 0.062 Uiso 1 1 calc R U . . .
C4 C -0.04257(18) 0.70458(18) 0.30060(15) 0.0565(4) Uani 1 1 d . . . . .
H4 H -0.122849 0.755801 0.244946 0.068 Uiso 1 1 calc R U . . .
C5 C 0.07867(18) 0.57244(18) 0.27302(13) 0.0512(3) Uani 1 1 d . . . . .
C2 C 0.08046(18) 0.67701(17) 0.49561(14) 0.0529(4) Uani 1 1 d . . . . .
H2 H 0.085062 0.711326 0.572782 0.063 Uiso 1 1 calc R U . . .
C3 C -0.03871(19) 0.75657(18) 0.41424(16) 0.0600(4) Uani 1 1 d . . . . .
H3 H -0.117043 0.846151 0.436613 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5083(2) 0.17148(19) 1.13554(13) 0.0570(4) Uani 1 1 d . . . . .
H14A H 0.490344 0.078225 1.110459 0.068 Uiso 1 1 calc R U . . .
H14B H 0.412196 0.231158 1.177653 0.068 Uiso 1 1 calc R U . . .
C15 C 0.6449(2) 0.1268(2) 1.21984(15) 0.0686(5) Uani 1 1 d . . . . .
H15A H 0.622390 0.064441 1.291988 0.103 Uiso 1 1 calc R U . . .
H15B H 0.739337 0.067349 1.177606 0.103 Uiso 1 1 calc R U . . .
H15C H 0.661469 0.219734 1.244560 0.103 Uiso 1 1 calc R U . . .
C12 C 0.8510(2) -0.0506(2) 0.75655(17) 0.0648(4) Uani 1 1 d . . . . .
H12A H 0.936908 -0.043148 0.698307 0.078 Uiso 1 1 calc R U . . .
H12B H 0.821136 -0.142451 0.742857 0.078 Uiso 1 1 calc R U . . .
C13 C 0.9029(2) -0.0621(3) 0.88614(19) 0.0841(6) Uani 1 1 d . . . . .
H13A H 0.993208 -0.153820 0.900987 0.126 Uiso 1 1 calc R U . . .
H13B H 0.932054 0.029434 0.898413 0.126 Uiso 1 1 calc R U . . .
H13C H 0.816836 -0.069394 0.942750 0.126 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
Cl1 C5 1.7298(15) . ?
O3 C11 1.3341(15) . ?
O3 C14 1.4539(17) . ?
O2 C10 1.3322(17) . ?
O2 C12 1.4525(19) . ?
O4 C11 1.1954(16) . ?
N3 C8 1.3210(18) . ?
N3 N2 1.3674(14) . ?
N2 C6 1.3446(17) . ?
N2 C1 1.4143(17) . ?
O1 C10 1.2015(18) . ?
N1 C5 1.3234(18) . ?
N1 C1 1.3252(17) . ?
C11 C9 1.4983(18) . ?
C7 C6 1.3695(18) . ?
C7 C8 1.4218(18) . ?
C7 C10 1.459(2) . ?
C8 C9 1.4974(17) . ?
C1 C2 1.3802(19) . ?
C4 C3 1.370(2) . ?
C4 C5 1.379(2) . ?
C2 C3 1.378(2) . ?
C14 C15 1.481(2) . ?
C12 C13 1.486(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
C11 O3 C14 117.14(11) . . ?
C10 O2 C12 115.93(12) . . ?
C8 N3 N2 104.76(10) . . ?
C6 N2 N3 112.25(11) . . ?
C6 N2 C1 127.17(11) . . ?
N3 N2 C1 120.52(11) . . ?
C5 N1 C1 116.05(12) . . ?
O4 C11 O3 124.49(12) . . ?
O4 C11 C9 125.27(12) . . ?
O3 C11 C9 110.23(11) . . ?
C6 C7 C8 104.92(12) . . ?
C6 C7 C10 123.16(12) . . ?
C8 C7 C10 131.91(12) . . ?
N3 C8 C7 111.10(11) . . ?
N3 C8 C9 119.56(12) . . ?
C7 C8 C9 129.34(13) . . ?
N1 C1 C2 124.39(13) . . ?
N1 C1 N2 114.24(11) . . ?
C2 C1 N2 121.36(12) . . ?
N2 C6 C7 106.97(11) . . ?
O1 C10 O2 123.37(14) . . ?
O1 C10 C7 124.14(13) . . ?
O2 C10 C7 112.49(12) . . ?
C8 C9 C11 113.64(11) . . ?
C3 C4 C5 116.58(14) . . ?
N1 C5 C4 125.33(14) . . ?
N1 C5 Cl1 115.30(11) . . ?
C4 C5 Cl1 119.37(11) . . ?
C3 C2 C1 117.16(14) . . ?
C4 C3 C2 120.46(14) . . ?
O3 C14 C15 108.35(14) . . ?
O2 C12 C13 106.91(15) . . ?

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_SR
_database_code_depnum_ccdc_archive 'CCDC 1966437'
_audit_update_record             
;
2019-11-18 deposited with the CCDC.	2020-04-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24

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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   5.6602(5)
_cell_length_b                   19.0351(18)
_cell_length_c                   10.7528(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.9260(10)
_cell_angle_gamma                90
_cell_volume                     1129.18(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    7529
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.02

_exptl_crystal_description       Block
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10663
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         25.059
_diffrn_reflns_theta_full        25.059
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2002
_reflns_number_gt                1783
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0666P)²+0.1080P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.142(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2002
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001

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
C1 C 0.2012(3) 0.32799(8) 0.33787(14) 0.0719(4) Uani 1 1 d . . . . .
H1 H 0.322558 0.363375 0.350014 0.086 Uiso 1 1 calc R U . . .
C2 C 0.1933(3) 0.27697(9) 0.24602(16) 0.0822(5) Uani 1 1 d . . . . .
H2 H 0.312225 0.276964 0.196155 0.099 Uiso 1 1 calc R U . . .
C3 C 0.0178(3) 0.22654(9) 0.22543(16) 0.0803(5) Uani 1 1 d . . . . .
H3 H 0.012517 0.192115 0.160892 0.096 Uiso 1 1 calc R U . . .
C4 C -0.1505(3) 0.22622(8) 0.29910(17) 0.0835(5) Uani 1 1 d . . . . .
H4 H -0.273416 0.191252 0.285273 0.100 Uiso 1 1 calc R U . . .
C5 C -0.1444(3) 0.27600(7) 0.39326(14) 0.0702(4) Uani 1 1 d . . . . .
H5 H -0.260678 0.274908 0.444718 0.084 Uiso 1 1 calc R U . . .
C6 C 0.0317(2) 0.32718(6) 0.41180(11) 0.0539(3) Uani 1 1 d . . . . .
C7 C 0.2202(2) 0.42342(6) 0.55784(12) 0.0546(3) Uani 1 1 d . . . . .
H7 H 0.369409 0.428312 0.532111 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1495(2) 0.46032(6) 0.65250(11) 0.0546(3) Uani 1 1 d . . . . .
C9 C -0.0820(2) 0.43472(7) 0.65256(12) 0.0632(4) Uani 1 1 d . . . . .
H9 H -0.178268 0.450937 0.708605 0.076 Uiso 1 1 calc R U . . .
C10 C 0.2903(2) 0.51386(7) 0.73421(13) 0.0617(4) Uani 1 1 d . . . . .
C11 C 0.2936(3) 0.58972(9) 0.91027(17) 0.0911(5) Uani 1 1 d . . . . .
H11A H 0.301399 0.634051 0.863211 0.109 Uiso 1 1 calc R U . . .
H11B H 0.460645 0.575603 0.952496 0.109 Uiso 1 1 calc R U . . .
C12 C 0.1447(5) 0.59932(12) 1.0061(2) 0.1313(9) Uani 1 1 d . . . . .
H12A H 0.217058 0.635959 1.066833 0.197 Uiso 1 1 calc R U . . .
H12B H -0.019907 0.613261 0.963069 0.197 Uiso 1 1 calc R U . . .
H12C H 0.138605 0.555083 1.051943 0.197 Uiso 1 1 calc R U . . .
N1 N 0.03943(17) 0.37901(5) 0.50808(9) 0.0525(3) Uani 1 1 d . . . . .
N2 N -0.15088(19) 0.38566(6) 0.56614(10) 0.0640(3) Uani 1 1 d . . . . .
O1 O 0.4838(2) 0.53608(6) 0.72378(13) 0.0923(4) Uani 1 1 d . . . . .
O2 O 0.17804(19) 0.53517(5) 0.82371(9) 0.0764(3) 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
C1 C6 1.3760(18) . ?
C1 C2 1.379(2) . ?
C2 C3 1.363(2) . ?
C3 C4 1.369(2) . ?
C4 C5 1.381(2) . ?
C5 C6 1.3763(18) . ?
C6 N1 1.4236(15) . ?
C7 N1 1.3430(15) . ?
C7 C8 1.3681(17) . ?
C8 C9 1.3981(18) . ?
C8 C10 1.4601(18) . ?
C9 N2 1.3138(17) . ?
C10 O1 1.2025(17) . ?
C10 O2 1.3296(16) . ?
C11 O2 1.4490(17) . ?
C11 C12 1.482(3) . ?
N1 N2 1.3664(14) . ?

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
C6 C1 C2 119.39(13) . . ?
C3 C2 C1 121.22(14) . . ?
C2 C3 C4 119.03(14) . . ?
C3 C4 C5 120.97(14) . . ?
C6 C5 C4 119.36(13) . . ?
C5 C6 C1 120.02(12) . . ?
C5 C6 N1 119.95(11) . . ?
C1 C6 N1 120.03(11) . . ?
N1 C7 C8 107.21(10) . . ?
C7 C8 C9 104.57(11) . . ?
C7 C8 C10 126.51(11) . . ?
C9 C8 C10 128.91(12) . . ?
N2 C9 C8 112.18(11) . . ?
O1 C10 O2 123.55(13) . . ?
O1 C10 C8 125.10(13) . . ?
O2 C10 C8 111.34(11) . . ?
O2 C11 C12 106.86(15) . . ?
C7 N1 N2 111.60(10) . . ?
C7 N1 C6 128.51(10) . . ?
N2 N1 C6 119.83(10) . . ?
C9 N2 N1 104.44(10) . . ?
C10 O2 C11 117.61(12) . . ?

_refine_diff_density_max         0.142
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.040



