# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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. 
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data_1-(4-nitrobenzyl)-1H-benzimidazole
_database_code_depnum_ccdc_archive 'CCDC 1552582'
_audit_update_record             
;
2017-05-26 deposited with the CCDC.
2017-07-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H24 N6 O5'
_chemical_formula_weight         524.53

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                   7.4948(18)
_cell_length_b                   10.427(2)
_cell_length_c                   32.549(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2543.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    302(2)
_cell_measurement_reflns_used    3689
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_F_000             1096
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.828
_exptl_absorpt_process_details   
;
R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      302(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22891
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.176
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5774
_reflns_number_gt                3467
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_max     0.976
_reflns_Friedel_fraction_full    0.996

_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       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0837P)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 1166 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.3(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5774
_refine_ls_number_parameters     360
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1605
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
O18 O 0.3548(11) 0.5390(8) 0.27379(18) 0.204(4) Uani 1 1 d . . . . .
O19 O 0.4049(9) 0.7272(7) 0.2505(2) 0.220(4) Uani 1 1 d . . . . .
N1 N 0.1781(4) 0.4503(3) 0.05750(9) 0.0598(8) Uani 1 1 d . . . . .
N8 N -0.0104(5) 0.5453(3) 0.01407(10) 0.0665(9) Uani 1 1 d . . . . .
N17 N 0.3729(8) 0.6204(9) 0.2452(2) 0.143(3) Uani 1 1 d . . . . .
C2 C 0.0317(5) 0.3710(3) 0.05548(10) 0.0508(9) Uani 1 1 d . . . . .
C3 C -0.0074(6) 0.2539(4) 0.07331(12) 0.0657(11) Uani 1 1 d . . . . .
H3 H 0.0709 0.2142 0.0915 0.079 Uiso 1 1 calc R U . . .
C4 C -0.1663(7) 0.1999(4) 0.06290(13) 0.0742(12) Uani 1 1 d . . . . .
H4 H -0.1968 0.1210 0.0742 0.089 Uiso 1 1 calc R U . . .
C5 C -0.2845(6) 0.2586(4) 0.03597(13) 0.0695(11) Uani 1 1 d . . . . .
H5 H -0.3918 0.2183 0.0297 0.083 Uiso 1 1 calc R U . . .
C6 C -0.2454(6) 0.3760(4) 0.01821(12) 0.0620(10) Uani 1 1 d . . . . .
H6 H -0.3248 0.4155 0.0003 0.074 Uiso 1 1 calc R U . . .
C7 C -0.0848(5) 0.4320(3) 0.02811(10) 0.0523(9) Uani 1 1 d . . . . .
C9 C 0.1445(6) 0.5497(4) 0.03243(12) 0.0702(11) Uani 1 1 d . . . . .
H9 H 0.2250 0.6163 0.0284 0.084 Uiso 1 1 calc R U . . .
C10 C 0.3402(6) 0.4297(4) 0.08144(13) 0.0710(11) Uani 1 1 d . . . . .
H10A H 0.4390 0.4710 0.0674 0.085 Uiso 1 1 calc R U . . .
H10B H 0.3650 0.3385 0.0823 0.085 Uiso 1 1 calc R U . . .
C11 C 0.3320(5) 0.4793(3) 0.12474(12) 0.0562(9) Uani 1 1 d . . . . .
C12 C 0.3070(6) 0.6071(4) 0.13305(14) 0.0722(12) Uani 1 1 d . . . . .
H12 H 0.2818 0.6631 0.1116 0.087 Uiso 1 1 calc R U . . .
C13 C 0.3183(7) 0.6538(4) 0.17224(19) 0.0844(14) Uani 1 1 d . . . . .
H13 H 0.3042 0.7408 0.1777 0.101 Uiso 1 1 calc R U . . .
C14 C 0.3514(6) 0.5672(5) 0.20357(15) 0.0816(14) Uani 1 1 d . . . . .
C15 C 0.3710(7) 0.4419(5) 0.19651(14) 0.0867(14) Uani 1 1 d . . . . .
H15 H 0.3910 0.3854 0.2181 0.104 Uiso 1 1 calc R U . . .
C16 C 0.3613(6) 0.3981(4) 0.15723(13) 0.0720(12) Uani 1 1 d . . . . .
H16 H 0.3750 0.3108 0.1523 0.086 Uiso 1 1 calc R U . . .
O37 O 0.9557(9) 0.3551(5) 0.2440(2) 0.192(3) Uani 1 1 d . . . . .
O38 O 0.9262(9) 0.2591(4) 0.18809(19) 0.183(3) Uani 1 1 d . . . . .
N20 N 0.8963(5) 0.8688(3) 0.10588(9) 0.0586(8) Uani 1 1 d . . . . .
N22 N 1.0775(6) 0.8791(3) 0.05163(10) 0.0677(9) Uani 1 1 d . . . . .
N36 N 0.9215(8) 0.3534(6) 0.2074(2) 0.1218(19) Uani 1 1 d . . . . .
C21 C 0.9237(7) 0.8425(4) 0.06564(12) 0.0682(12) Uani 1 1 d . . . . .
H21 H 0.8391 0.8015 0.0494 0.082 Uiso 1 1 calc R U . . .
C23 C 1.1630(5) 0.9349(3) 0.08532(10) 0.0547(9) Uani 1 1 d . . . . .
C24 C 1.3275(6) 0.9906(3) 0.08833(13) 0.0638(10) Uani 1 1 d . . . . .
H24 H 1.4028 0.9956 0.0657 0.077 Uiso 1 1 calc R U . . .
C25 C 1.3784(6) 1.0391(4) 0.12587(14) 0.0696(11) Uani 1 1 d . . . . .
H25 H 1.4904 1.0764 0.1288 0.083 Uiso 1 1 calc R U . . .
C26 C 1.2641(7) 1.0330(4) 0.15958(15) 0.0767(13) Uani 1 1 d . . . . .
H26 H 1.3016 1.0666 0.1846 0.092 Uiso 1 1 calc R U . . .
C27 C 1.0976(7) 0.9788(4) 0.15687(12) 0.0676(11) Uani 1 1 d . . . . .
H27 H 1.0204 0.9763 0.1792 0.081 Uiso 1 1 calc R U . . .
C28 C 1.0508(5) 0.9283(3) 0.11933(11) 0.0542(9) Uani 1 1 d . . . . .
C29 C 0.7457(6) 0.8248(4) 0.13066(13) 0.0671(11) Uani 1 1 d . . . . .
H29A H 0.6415 0.8154 0.1132 0.081 Uiso 1 1 calc R U . . .
H29B H 0.7187 0.8886 0.1514 0.081 Uiso 1 1 calc R U . . .
C30 C 0.7855(5) 0.6986(3) 0.15120(10) 0.0515(8) Uani 1 1 d . . . . .
C31 C 0.8240(6) 0.6955(4) 0.19232(12) 0.0682(11) Uani 1 1 d . . . . .
H31 H 0.8211 0.7712 0.2074 0.082 Uiso 1 1 calc R U . . .
C32 C 0.8659(7) 0.5852(5) 0.21132(14) 0.0813(13) Uani 1 1 d . . . . .
H32 H 0.8906 0.5842 0.2393 0.098 Uiso 1 1 calc R U . . .
C33 C 0.8716(6) 0.4757(4) 0.18910(15) 0.0751(13) Uani 1 1 d . . . . .
C34 C 0.8308(7) 0.4739(4) 0.14718(14) 0.0762(13) Uani 1 1 d . . . . .
H34 H 0.8323 0.3978 0.1323 0.091 Uiso 1 1 calc R U . . .
C35 C 0.7882(6) 0.5888(3) 0.12863(11) 0.0604(10) Uani 1 1 d . . . . .
H35 H 0.7613 0.5912 0.1007 0.073 Uiso 1 1 calc R U . . .
O90 O 0.5357(5) 0.7137(3) 0.03264(9) 0.0704(8) Uani 1 1 d . . . . .
H90A H 0.493(7) 0.801(5) 0.0193(16) 0.115(17) Uiso 1 1 d . . . . .
H90B H 0.574(7) 0.675(4) 0.0113(16) 0.088(17) 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
O18 N17 1.268(10) . ?
O19 N17 1.152(10) . ?
N1 C9 1.343(5) . ?
N1 C2 1.375(5) . ?
N1 C10 1.459(5) . ?
N8 C9 1.306(5) . ?
N8 C7 1.383(4) . ?
N17 C14 1.472(8) . ?
C2 C3 1.383(5) . ?
C2 C7 1.401(5) . ?
C3 C4 1.360(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(5) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.503(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.372(5) . ?
C11 C16 1.373(5) . ?
C12 C13 1.368(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.385(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.334(7) . ?
C15 C16 1.360(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
O37 N36 1.219(8) . ?
O38 N36 1.169(7) . ?
N20 C21 1.354(5) . ?
N20 C28 1.385(5) . ?
N20 C29 1.461(5) . ?
N22 C21 1.297(6) . ?
N22 C23 1.397(5) . ?
N36 C33 1.456(6) . ?
C21 H21 0.9300 . ?
C23 C24 1.366(6) . ?
C23 C28 1.392(5) . ?
C24 C25 1.376(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.393(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.373(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(5) . ?
C27 H27 0.9300 . ?
C29 C30 1.506(5) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C35 1.361(5) . ?
C30 C31 1.369(5) . ?
C31 C32 1.342(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.353(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.399(6) . ?
C34 C35 1.379(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
O90 H90A 1.06(6) . ?
O90 H90B 0.85(5) . ?

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
C9 N1 C2 106.6(3) . . ?
C9 N1 C10 126.5(4) . . ?
C2 N1 C10 127.0(3) . . ?
C9 N8 C7 103.7(3) . . ?
O19 N17 O18 124.0(8) . . ?
O19 N17 C14 121.7(9) . . ?
O18 N17 C14 114.3(8) . . ?
N1 C2 C3 132.8(4) . . ?
N1 C2 C7 104.8(3) . . ?
C3 C2 C7 122.4(4) . . ?
C4 C3 C2 116.5(4) . . ?
C4 C3 H3 121.7 . . ?
C2 C3 H3 121.7 . . ?
C3 C4 C5 122.2(4) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C7 C6 C5 117.5(4) . . ?
C7 C6 H6 121.2 . . ?
C5 C6 H6 121.2 . . ?
C6 C7 N8 129.6(4) . . ?
C6 C7 C2 120.1(3) . . ?
N8 C7 C2 110.3(3) . . ?
N8 C9 N1 114.7(4) . . ?
N8 C9 H9 122.6 . . ?
N1 C9 H9 122.6 . . ?
N1 C10 C11 114.6(3) . . ?
N1 C10 H10A 108.6 . . ?
C11 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C11 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C16 118.0(4) . . ?
C12 C11 C10 121.6(4) . . ?
C16 C11 C10 120.2(3) . . ?
C13 C12 C11 121.4(4) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C12 C13 C14 117.8(4) . . ?
C12 C13 H13 121.1 . . ?
C14 C13 H13 121.1 . . ?
C15 C14 C13 122.1(4) . . ?
C15 C14 N17 121.0(6) . . ?
C13 C14 N17 116.8(6) . . ?
C14 C15 C16 119.0(5) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C11 121.7(4) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
C21 N20 C28 105.6(3) . . ?
C21 N20 C29 126.0(4) . . ?
C28 N20 C29 127.8(3) . . ?
C21 N22 C23 104.7(3) . . ?
O38 N36 O37 122.2(6) . . ?
O38 N36 C33 121.6(7) . . ?
O37 N36 C33 116.2(7) . . ?
N22 C21 N20 114.5(4) . . ?
N22 C21 H21 122.7 . . ?
N20 C21 H21 122.7 . . ?
C24 C23 C28 120.6(3) . . ?
C24 C23 N22 130.3(4) . . ?
C28 C23 N22 109.1(3) . . ?
C23 C24 C25 118.0(4) . . ?
C23 C24 H24 121.0 . . ?
C25 C24 H24 121.0 . . ?
C24 C25 C26 120.8(4) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C27 C26 C25 121.8(4) . . ?
C27 C26 H26 119.1 . . ?
C25 C26 H26 119.1 . . ?
C26 C27 C28 116.5(4) . . ?
C26 C27 H27 121.8 . . ?
C28 C27 H27 121.8 . . ?
C27 C28 N20 131.7(4) . . ?
C27 C28 C23 122.3(4) . . ?
N20 C28 C23 106.0(3) . . ?
N20 C29 C30 111.5(3) . . ?
N20 C29 H29A 109.3 . . ?
C30 C29 H29A 109.3 . . ?
N20 C29 H29B 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C35 C30 C31 120.3(4) . . ?
C35 C30 C29 119.9(3) . . ?
C31 C30 C29 119.8(3) . . ?
C32 C31 C30 121.3(4) . . ?
C32 C31 H31 119.3 . . ?
C30 C31 H31 119.3 . . ?
C31 C32 C33 118.9(4) . . ?
C31 C32 H32 120.5 . . ?
C33 C32 H32 120.5 . . ?
C32 C33 C34 121.7(4) . . ?
C32 C33 N36 121.9(5) . . ?
C34 C33 N36 116.4(5) . . ?
C35 C34 C33 117.8(4) . . ?
C35 C34 H34 121.1 . . ?
C33 C34 H34 121.1 . . ?
C30 C35 C34 119.9(4) . . ?
C30 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
H90A O90 H90B 100(4) . . ?

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

