# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_BSDprelim
_database_code_depnum_ccdc_archive 'CCDC 1430636'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Benzimidazole nucleosides'
_chemical_name_common            NA
_chemical_melting_point          '189-191 oC'
_chemical_formula_moiety         NA
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.7178(3)
_cell_length_b                   10.4187(5)
_cell_length_c                   24.9522(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1486.45(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       NA
_exptl_crystal_colour            NA
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9079
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.118
_diffrn_reflns_theta_max         25.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measured_fraction_theta_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2656
_reflns_number_gt                2257
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.965
_reflns_Friedel_fraction_full    0.965

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1401P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 851 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2656
_refine_ls_number_parameters     200
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0580
_refine_ls_wR_factor_ref         0.2029
_refine_ls_wR_factor_gt          0.1795
_refine_ls_goodness_of_fit_ref   1.220
_refine_ls_restrained_S_all      1.237
_refine_ls_shift/su_max          0.004
_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
N2 N 0.2481(6) 0.4086(3) 0.75715(14) 0.0402(8) Uani 1 1 d . . . . .
N1 N -0.0660(6) 0.3018(3) 0.72938(17) 0.0526(10) Uani 1 1 d . . . . .
C1 C 0.0844(7) 0.3180(4) 0.76840(18) 0.0469(10) Uani 1 1 d . . . . .
H1 H 0.0796 0.2723 0.8004 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2021(7) 0.4545(4) 0.70675(18) 0.0457(10) Uani 1 1 d . . . . .
C2 C 0.0011(8) 0.3885(4) 0.68944(19) 0.0518(11) Uani 1 1 d . . . . .
C4 C 0.3138(10) 0.5459(4) 0.6744(2) 0.0615(13) Uani 1 1 d . . . . .
H4 H 0.4453 0.5906 0.6859 0.074 Uiso 1 1 calc R U . . .
C7 C -0.0929(10) 0.4152(5) 0.6385(2) 0.0693(15) Uani 1 1 d . . . . .
H7 H -0.2284 0.3746 0.6268 0.083 Uiso 1 1 calc R U . . .
C6 C 0.0190(15) 0.5017(5) 0.6069(2) 0.086(2) Uani 1 1 d . . . . .
H6 H -0.0391 0.5182 0.5727 0.103 Uiso 1 1 calc R U . . .
C5 C 0.2159(14) 0.5656(5) 0.6239(2) 0.0806(18) Uani 1 1 d . . . . .
H5 H 0.2863 0.6242 0.6009 0.097 Uiso 1 1 calc R U . . .
O1 O 0.4857(6) 0.3491(2) 0.82829(13) 0.0531(8) Uani 1 1 d . . . . .
C9 C 0.4379(6) 0.5706(3) 0.81872(17) 0.0403(9) Uani 1 1 d . . . . .
H9 H 0.2850 0.5792 0.8361 0.048 Uiso 1 1 calc R U . . .
C8 C 0.4538(6) 0.4426(3) 0.78831(17) 0.0414(9) Uani 1 1 d . . . . .
C10 C 0.6297(7) 0.5494(3) 0.86056(17) 0.0427(9) Uani 1 1 d . . . . .
C11 C 0.5908(9) 0.4066(4) 0.87494(18) 0.0533(11) Uani 1 1 d . . . . .
H11 H 0.7451 0.3673 0.8798 0.064 Uiso 1 1 calc R U . . .
O2 O 0.4849(5) 0.6775(2) 0.78691(13) 0.0469(8) Uani 1 1 d D . . . .
H22 H 0.378(8) 0.688(5) 0.7641(18) 0.070 Uiso 1 1 d D U . . .
O3 O 0.8510(5) 0.5544(3) 0.83340(13) 0.0472(7) Uani 1 1 d D . . . .
H33 H 0.860(13) 0.533(6) 0.8021(12) 0.071 Uiso 1 1 d D U . . .
C12 C 0.6302(9) 0.6463(4) 0.90635(19) 0.0580(12) Uani 1 1 d . . . . .
H12A H 0.6279 0.7324 0.8915 0.070 Uiso 1 1 calc R U . . .
H12B H 0.4893 0.6352 0.9275 0.070 Uiso 1 1 calc R U . . .
C13 C 0.8397(12) 0.6325(6) 0.9422(2) 0.0790(17) Uani 1 1 d D . . . .
H13 H 0.9857 0.6279 0.9259 0.095 Uiso 1 1 calc R U . . .
C14 C 0.8335(17) 0.6263(7) 0.9951(3) 0.108(3) Uani 1 1 d D . . . .
H14A H 0.6910 0.6305 1.0130 0.129 Uiso 1 1 calc R U . . .
H14B H 0.9717 0.6177 1.0145 0.129 Uiso 1 1 calc R U . . .
C15 C 0.4595(16) 0.3836(6) 0.9227(3) 0.117(3) Uani 1 1 d D . . . .
H15 H 0.5196 0.4200 0.9538 0.140 Uiso 1 1 calc R U . . .
C16 C 0.2645(18) 0.3177(10) 0.9284(5) 0.168(5) Uani 1 1 d D . . . .
H16A H 0.1954 0.2789 0.8988 0.201 Uiso 1 1 calc R U . . .
H16B H 0.1959 0.3100 0.9621 0.201 Uiso 1 1 calc R U . . .
H8 H 0.598(8) 0.455(4) 0.7598(17) 0.042(10) 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
N2 C1 1.358(5) . ?
N2 C3 1.371(6) . ?
N2 C8 1.454(5) . ?
N1 C1 1.310(5) . ?
N1 C2 1.399(6) . ?
C3 C4 1.403(7) . ?
C3 C2 1.407(6) . ?
C2 C7 1.408(7) . ?
C4 C5 1.392(8) . ?
C7 C6 1.358(9) . ?
C6 C5 1.376(10) . ?
O1 C8 1.406(5) . ?
O1 C11 1.440(5) . ?
C9 O2 1.394(5) . ?
C9 C10 1.530(5) . ?
C9 C8 1.537(5) . ?
C10 O3 1.437(5) . ?
C10 C12 1.525(6) . ?
C10 C11 1.547(5) . ?
C11 C15 1.428(8) . ?
C12 C13 1.503(8) . ?
C13 C14 1.321(6) . ?
C15 C16 1.317(6) . ?

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
C1 N2 C3 107.4(4) . . ?
C1 N2 C8 128.0(4) . . ?
C3 N2 C8 124.1(3) . . ?
C1 N1 C2 105.4(3) . . ?
N1 C1 N2 112.8(4) . . ?
N2 C3 C4 132.7(4) . . ?
N2 C3 C2 105.6(4) . . ?
C4 C3 C2 121.8(4) . . ?
N1 C2 C3 108.7(4) . . ?
N1 C2 C7 131.8(4) . . ?
C3 C2 C7 119.5(5) . . ?
C5 C4 C3 115.9(5) . . ?
C6 C7 C2 118.4(5) . . ?
C7 C6 C5 121.8(6) . . ?
C6 C5 C4 122.5(6) . . ?
C8 O1 C11 109.9(3) . . ?
O2 C9 C10 111.4(3) . . ?
O2 C9 C8 113.6(4) . . ?
C10 C9 C8 99.8(3) . . ?
O1 C8 N2 108.4(3) . . ?
O1 C8 C9 105.0(3) . . ?
N2 C8 C9 115.3(3) . . ?
O3 C10 C12 109.1(3) . . ?
O3 C10 C9 107.7(3) . . ?
C12 C10 C9 114.7(3) . . ?
O3 C10 C11 105.7(3) . . ?
C12 C10 C11 117.6(4) . . ?
C9 C10 C11 101.2(3) . . ?
C15 C11 O1 112.7(5) . . ?
C15 C11 C10 115.5(4) . . ?
O1 C11 C10 105.8(3) . . ?
C13 C12 C10 112.6(4) . . ?
C14 C13 C12 125.3(7) . . ?
C16 C15 C11 128.5(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H9 O3 0.98 2.50 3.380(4) 149.9 1_455
C9 H9 O3 0.98 2.50 3.380(4) 149.9 1_455
O2 H22 N1 0.84(3) 2.15(5) 2.753(4) 129(5) 3_556
C8 H8 N1 1.10(4) 2.61(4) 3.443(5) 132(3) 1_655
C9 H9 O3 0.98 2.50 3.380(4) 149.9 1_455
O2 H22 N1 0.84(3) 2.15(5) 2.753(4) 129(5) 3_556
C8 H8 N1 1.10(4) 2.61(4) 3.443(5) 132(3) 1_655

_refine_diff_density_max         0.511
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.123

_shelxl_version_number           2014/6


_chemical_compound_source        NA
####################################################################### 
# 
# 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_BNU2P21212
_database_code_depnum_ccdc_archive 'CCDC 1430637'
_audit_update_record             
;
2016-03-08 deposited with the CCDC.
2016-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Bicyclic benzimidazole nucleoside'
_chemical_name_common            NA
_chemical_melting_point          '112-114 oC'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 Cl N2 O3'
_chemical_formula_weight         292.71

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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'

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

_cell_length_a                   13.7554(4)
_cell_length_b                   18.6455(5)
_cell_length_c                   5.38910(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1382.18(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.285
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12954
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.840
_diffrn_reflns_theta_max         31.978
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             4311
_reflns_number_gt                3811
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_max     0.832
_reflns_Friedel_fraction_full    0.892

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0968P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(18)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4311
_refine_ls_number_parameters     206
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.848
_refine_ls_shift/su_mean         0.039

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 0.72915(5) 0.26333(3) 1.07825(14) 0.0496(2) Uani 1 1 d . . . . .
C3 C 0.59758(13) 0.36097(9) 0.5483(4) 0.0289(4) Uani 1 1 d . . . . .
C1 C 0.65793(14) 0.29096(10) 0.8374(5) 0.0334(5) Uani 1 1 d . . . . .
C4 C 0.57224(14) 0.41376(11) 0.3782(5) 0.0334(4) Uani 1 1 d . . . . .
H4 H 0.6009 0.4589 0.3815 0.040 Uiso 1 1 calc R U . . .
C2 C 0.55409(14) 0.29265(10) 0.5447(5) 0.0342(5) Uani 1 1 d . . . . .
C6 C 0.45903(18) 0.32773(13) 0.1993(6) 0.0431(6) Uani 1 1 d . . . . .
H6 H 0.4129 0.3174 0.0784 0.052 Uiso 1 1 calc R U . . .
C5 C 0.50231(15) 0.39607(13) 0.2036(5) 0.0382(5) Uani 1 1 d . . . . .
H5 H 0.4836 0.4301 0.0867 0.046 Uiso 1 1 calc R U . . .
C7 C 0.48319(16) 0.27595(12) 0.3689(5) 0.0418(5) Uani 1 1 d . . . . .
H7 H 0.4533 0.2312 0.3669 0.050 Uiso 1 1 calc R U . . .
N2 N 0.66574(11) 0.35877(8) 0.7397(4) 0.0310(4) Uani 1 1 d . . . . .
N1 N 0.59419(14) 0.24991(9) 0.7299(4) 0.0386(4) Uani 1 1 d . . . . .
O1 O 0.66172(10) 0.47658(7) 0.8740(3) 0.0369(4) Uani 1 1 d . . . . .
C10 C 0.82334(13) 0.51994(10) 0.7805(4) 0.0286(4) Uani 1 1 d . . . . .
C11 C 0.72031(13) 0.54136(10) 0.8630(4) 0.0291(4) Uani 1 1 d . . . . .
H11 H 0.7220 0.5652 1.0250 0.035 Uiso 1 1 calc R U . . .
C8 C 0.72436(14) 0.41731(9) 0.8344(4) 0.0293(4) Uani 1 1 d . . . . .
H8 H 0.7537 0.4030 0.9925 0.035 Uiso 1 1 calc R U . . .
O2 O 0.88483(11) 0.40086(9) 0.6400(4) 0.0434(5) Uani 1 1 d D . . . .
O3 O 0.88695(12) 0.50789(9) 0.9812(4) 0.0425(4) Uani 1 1 d D . . . .
C12 C 0.85452(16) 0.57790(12) 0.5953(5) 0.0377(5) Uani 1 1 d . . . . .
H12B H 0.8978 0.6124 0.6723 0.045 Uiso 1 1 calc R U . . .
H12A H 0.8867 0.5570 0.4524 0.045 Uiso 1 1 calc R U . . .
C13 C 0.75997(18) 0.61213(12) 0.5231(5) 0.0407(5) Uani 1 1 d . . . . .
H13 H 0.7533 0.6441 0.3918 0.049 Uiso 1 1 calc R U . . .
C14 C 0.68718(16) 0.59185(11) 0.6666(5) 0.0367(5) Uani 1 1 d . . . . .
H14 H 0.6233 0.6072 0.6474 0.044 Uiso 1 1 calc R U . . .
C9 C 0.80345(12) 0.44577(10) 0.6614(4) 0.0286(4) Uani 1 1 d . . . . .
H9 H 0.7754 0.4531 0.4961 0.034 Uiso 1 1 calc R U . . .
O4 O 0.01215(16) 0.62628(11) 0.1090(5) 0.0544(5) Uani 1 1 d D . . . .
H22 H 0.924(4) 0.387(3) 0.754(10) 0.17(3) Uiso 1 1 d D . . . .
H41 H 0.058(3) 0.640(3) 0.198(10) 0.106(19) Uiso 1 1 d D . . . .
H42 H -0.015(2) 0.6660(13) 0.133(7) 0.060(10) Uiso 1 1 d D . . . .
H33 H 0.919(3) 0.541(2) 1.032(12) 0.119(18) Uiso 1 1 d 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
Cl1 C1 1.706(2) . ?
C3 C4 1.389(3) . ?
C3 N2 1.394(3) . ?
C3 C2 1.408(2) . ?
C1 N1 1.300(3) . ?
C1 N2 1.374(2) . ?
C4 C5 1.386(3) . ?
C2 N1 1.391(3) . ?
C2 C7 1.395(3) . ?
C6 C7 1.371(4) . ?
C6 C5 1.407(3) . ?
N2 C8 1.450(2) . ?
O1 C8 1.418(2) . ?
O1 C11 1.453(2) . ?
C10 O3 1.410(3) . ?
C10 C12 1.532(3) . ?
C10 C11 1.538(3) . ?
C10 C9 1.549(3) . ?
C11 C14 1.488(3) . ?
C8 C9 1.528(3) . ?
O2 C9 1.403(2) . ?
C12 C13 1.500(3) . ?
C13 C14 1.320(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
C4 C3 N2 132.66(17) . . ?
C4 C3 C2 121.7(2) . . ?
N2 C3 C2 105.61(18) . . ?
N1 C1 N2 115.1(2) . . ?
N1 C1 Cl1 123.28(16) . . ?
N2 C1 Cl1 121.66(17) . . ?
C5 C4 C3 116.98(19) . . ?
N1 C2 C7 129.53(18) . . ?
N1 C2 C3 109.9(2) . . ?
C7 C2 C3 120.6(2) . . ?
C7 C6 C5 121.6(2) . . ?
C4 C5 C6 121.4(2) . . ?
C6 C7 C2 117.7(2) . . ?
C1 N2 C3 104.97(16) . . ?
C1 N2 C8 127.0(2) . . ?
C3 N2 C8 127.73(16) . . ?
C1 N1 C2 104.47(17) . . ?
C8 O1 C11 107.74(14) . . ?
O3 C10 C12 116.02(17) . . ?
O3 C10 C11 113.04(19) . . ?
C12 C10 C11 105.25(16) . . ?
O3 C10 C9 106.58(15) . . ?
C12 C10 C9 114.16(19) . . ?
C11 C10 C9 100.88(14) . . ?
O1 C11 C14 112.66(18) . . ?
O1 C11 C10 107.88(14) . . ?
C14 C11 C10 103.94(18) . . ?
O1 C8 N2 107.58(15) . . ?
O1 C8 C9 104.72(14) . . ?
N2 C8 C9 116.28(18) . . ?
C13 C12 C10 103.08(17) . . ?
C14 C13 C12 112.6(2) . . ?
C13 C14 C11 111.4(2) . . ?
O2 C9 C8 114.27(17) . . ?
O2 C9 C10 115.22(16) . . ?
C8 C9 C10 100.55(16) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 Cl1 0.98 2.67 3.158(2) 111.3 .
C7 H7 O2 0.93 2.64 3.564(3) 174.7 4_456

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.102

_shelxl_version_number           2014/6


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
