# 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 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_ar41
_database_code_depnum_ccdc_archive 'CCDC 925957'
_audit_update_record             
;
2013-02-21 deposited with the CCDC.
2015-03-09 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_B.Sridhar_1361443550.ar41f.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Cl N4 O4'
_chemical_formula_sum            'C20 H19 Cl N4 O4'
_chemical_formula_weight         414.84

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   11.2664(18)
_cell_length_b                   13.069(2)
_cell_length_c                   13.687(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.327(1)
_cell_angle_gamma                90.00
_cell_volume                     2015.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6443
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      24.85

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.224
_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      294(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  'CCD Area Detector'
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18997
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3547
_reflns_number_gt                2891
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL97

_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)+(0.0760P)²+0.8079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.38895(16) 0.23241(15) 1.15366(13) 0.0588(5) Uani 1 1 d . . .
C2 C 0.47095(19) 0.15626(16) 1.12729(15) 0.0528(5) Uani 1 1 d . . .
C3 C 0.4747(3) 0.05444(19) 1.15623(19) 0.0700(7) Uani 1 1 d . . .
H3 H 0.4158 0.0268 1.1956 0.084 Uiso 1 1 calc R . .
C4 C 0.5682(3) -0.00391(18) 1.1247(2) 0.0770(8) Uani 1 1 d . . .
H4 H 0.5729 -0.0722 1.1433 0.092 Uiso 1 1 calc R . .
C5 C 0.6554(2) 0.03680(18) 1.06603(19) 0.0683(7) Uani 1 1 d . . .
C6 C 0.6526(2) 0.13815(17) 1.03597(15) 0.0562(5) Uani 1 1 d . . .
H6 H 0.7114 0.1652 0.9962 0.067 Uiso 1 1 calc R . .
C7 C 0.55891(18) 0.19699(15) 1.06771(14) 0.0471(5) Uani 1 1 d . . .
C8 C 0.53393(19) 0.30956(15) 1.05384(14) 0.0478(5) Uani 1 1 d . . .
C9 C 0.4990(2) 0.33878(17) 0.94973(14) 0.0546(5) Uani 1 1 d . . .
H9A H 0.4258 0.3039 0.9325 0.066 Uiso 1 1 calc R . .
H9B H 0.4838 0.4118 0.9472 0.066 Uiso 1 1 calc R . .
C10 C 0.6906(2) 0.36155(16) 0.85632(15) 0.0562(6) Uani 1 1 d . . .
H10 H 0.7190 0.4218 0.8840 0.067 Uiso 1 1 calc R . .
C11 C 0.7437(2) 0.30460(17) 0.78540(15) 0.0549(5) Uani 1 1 d . . .
C12 C 0.8558(2) 0.3215(2) 0.73122(18) 0.0724(7) Uani 1 1 d . . .
H12A H 0.8431 0.3041 0.6631 0.087 Uiso 1 1 calc R . .
H12B H 0.8763 0.3935 0.7344 0.087 Uiso 1 1 calc R . .
C13 C 0.9995(2) 0.2950(2) 0.85606(18) 0.0656(6) Uani 1 1 d . . .
C14 C 0.9913(3) 0.2341(3) 0.9377(2) 0.1012(11) Uani 1 1 d . . .
H14 H 0.9495 0.1728 0.9346 0.121 Uiso 1 1 calc R . .
C15 C 1.0461(4) 0.2638(5) 1.0263(3) 0.1296(19) Uani 1 1 d . . .
H15 H 1.0419 0.2244 1.0827 0.156 Uiso 1 1 calc R . .
C16 C 1.1068(4) 0.3563(6) 1.0230(4) 0.145(2) Uani 1 1 d . . .
H16 H 1.1435 0.3778 1.0805 0.174 Uiso 1 1 calc R . .
C17 C 1.1173(3) 0.4167(4) 0.9458(4) 0.1233(15) Uani 1 1 d . . .
H17 H 1.1601 0.4774 0.9494 0.148 Uiso 1 1 calc R . .
C18 C 1.0632(2) 0.3871(2) 0.8602(2) 0.0805(8) Uani 1 1 d . . .
C19 C 1.1366(5) 0.5328(3) 0.7762(5) 0.178(3) Uani 1 1 d . . .
H19A H 1.1335 0.5628 0.8402 0.267 Uiso 1 1 calc R . .
H19B H 1.1034 0.5796 0.7293 0.267 Uiso 1 1 calc R . .
H19C H 1.2176 0.5186 0.7597 0.267 Uiso 1 1 calc R . .
O1 O 0.37387(18) 0.40614(15) 1.13356(13) 0.0803(5) Uani 1 1 d . . .
Cl1 Cl 0.77348(9) -0.04039(7) 1.02932(7) 0.1114(4) Uani 1 1 d . . .
C1 C 0.4228(2) 0.32551(18) 1.11842(15) 0.0558(5) Uani 1 1 d . . .
N2 N 0.58925(16) 0.31324(12) 0.87811(11) 0.0489(4) Uani 1 1 d . . .
N3 N 0.57727(17) 0.22816(13) 0.82345(12) 0.0528(4) Uani 1 1 d . . .
N4 N 0.67157(17) 0.22317(14) 0.76719(12) 0.0548(5) Uani 1 1 d . . .
C20 C 0.2895(2) 0.2177(3) 1.2201(2) 0.0835(8) Uani 1 1 d . . .
H20A H 0.2564 0.2830 1.2370 0.125 Uiso 1 1 calc R . .
H20B H 0.3168 0.1838 1.2782 0.125 Uiso 1 1 calc R . .
H20C H 0.2298 0.1766 1.1887 0.125 Uiso 1 1 calc R . .
O2 O 0.62772(15) 0.37450(11) 1.08164(12) 0.0584(4) Uani 1 1 d . . .
O3 O 0.95340(15) 0.26248(14) 0.76841(13) 0.0721(5) Uani 1 1 d . . .
O4 O 1.06963(19) 0.43934(17) 0.7753(2) 0.1041(7) Uani 1 1 d . . .
H1O H 0.651(2) 0.353(2) 1.134(2) 0.071(8) 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
N1 C1 1.364(3) . ?
N1 C2 1.406(3) . ?
N1 C20 1.460(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.393(3) . ?
C3 C4 1.372(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 Cl1 1.746(3) . ?
C6 C7 1.378(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.510(3) . ?
C8 O2 1.406(2) . ?
C8 C9 1.525(3) . ?
C8 C1 1.551(3) . ?
C9 N2 1.456(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.340(3) . ?
C10 C11 1.364(3) . ?
C10 H10 0.9300 . ?
C11 N4 1.361(3) . ?
C11 C12 1.485(3) . ?
C12 O3 1.434(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O3 1.372(3) . ?
C13 C14 1.376(4) . ?
C13 C18 1.403(4) . ?
C14 C15 1.411(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.325(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.372(5) . ?
C17 H17 0.9300 . ?
C18 O4 1.350(4) . ?
C19 O4 1.436(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
O1 C1 1.208(3) . ?
N2 N3 1.346(2) . ?
N3 N4 1.317(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 H1O 0.81(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
C1 N1 C2 110.79(18) . . ?
C1 N1 C20 123.7(2) . . ?
C2 N1 C20 125.0(2) . . ?
C3 C2 C7 120.8(2) . . ?
C3 C2 N1 128.6(2) . . ?
C7 C2 N1 110.52(18) . . ?
C4 C3 C2 117.7(2) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.3(2) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 Cl1 119.4(2) . . ?
C6 C5 Cl1 118.8(2) . . ?
C7 C6 C5 117.1(2) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C2 121.3(2) . . ?
C6 C7 C8 130.3(2) . . ?
C2 C7 C8 108.26(18) . . ?
O2 C8 C7 114.51(17) . . ?
O2 C8 C9 106.95(17) . . ?
C7 C8 C9 114.12(16) . . ?
O2 C8 C1 111.87(16) . . ?
C7 C8 C1 102.12(17) . . ?
C9 C8 C1 107.09(17) . . ?
N2 C9 C8 113.20(17) . . ?
N2 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
N2 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
N2 C10 C11 106.21(19) . . ?
N2 C10 H10 126.9 . . ?
C11 C10 H10 126.9 . . ?
N4 C11 C10 107.0(2) . . ?
N4 C11 C12 122.2(2) . . ?
C10 C11 C12 130.7(2) . . ?
O3 C12 C11 113.3(2) . . ?
O3 C12 H12A 108.9 . . ?
C11 C12 H12A 108.9 . . ?
O3 C12 H12B 108.9 . . ?
C11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O3 C13 C14 120.3(3) . . ?
O3 C13 C18 119.5(2) . . ?
C14 C13 C18 120.0(3) . . ?
C13 C14 C15 120.5(4) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 115.2(4) . . ?
C16 C15 H15 122.4 . . ?
C14 C15 H15 122.4 . . ?
C17 C16 C15 126.1(5) . . ?
C17 C16 H16 116.9 . . ?
C15 C16 H16 116.9 . . ?
C16 C17 C18 118.2(5) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
O4 C18 C17 124.5(4) . . ?
O4 C18 C13 115.4(2) . . ?
C17 C18 C13 120.1(4) . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 C1 N1 126.1(2) . . ?
O1 C1 C8 125.9(2) . . ?
N1 C1 C8 108.06(18) . . ?
C10 N2 N3 110.38(18) . . ?
C10 N2 C9 129.91(18) . . ?
N3 N2 C9 119.70(18) . . ?
N4 N3 N2 106.69(17) . . ?
N3 N4 C11 109.69(17) . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C8 O2 H1O 105.9(19) . . ?
C13 O3 C12 115.4(2) . . ?
C18 O4 C19 116.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 C3 173.4(2) . . . . ?
C20 N1 C2 C3 0.8(4) . . . . ?
C1 N1 C2 C7 -3.7(2) . . . . ?
C20 N1 C2 C7 -176.3(2) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
N1 C2 C3 C4 -176.3(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 Cl1 179.18(19) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
Cl1 C5 C6 C7 -179.05(15) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C5 C6 C7 C8 175.7(2) . . . . ?
C3 C2 C7 C6 -0.4(3) . . . . ?
N1 C2 C7 C6 176.98(18) . . . . ?
C3 C2 C7 C8 -176.9(2) . . . . ?
N1 C2 C7 C8 0.4(2) . . . . ?
C6 C7 C8 O2 -52.5(3) . . . . ?
C2 C7 C8 O2 123.62(18) . . . . ?
C6 C7 C8 C9 71.2(3) . . . . ?
C2 C7 C8 C9 -112.7(2) . . . . ?
C6 C7 C8 C1 -173.6(2) . . . . ?
C2 C7 C8 C1 2.52(19) . . . . ?
O2 C8 C9 N2 68.6(2) . . . . ?
C7 C8 C9 N2 -59.1(2) . . . . ?
C1 C8 C9 N2 -171.36(17) . . . . ?
N2 C10 C11 N4 -0.1(2) . . . . ?
N2 C10 C11 C12 178.2(2) . . . . ?
N4 C11 C12 O3 -81.8(3) . . . . ?
C10 C11 C12 O3 100.0(3) . . . . ?
O3 C13 C14 C15 175.4(3) . . . . ?
C18 C13 C14 C15 0.5(4) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C18 0.5(7) . . . . ?
C16 C17 C18 O4 -177.8(4) . . . . ?
C16 C17 C18 C13 -0.3(5) . . . . ?
O3 C13 C18 O4 2.6(3) . . . . ?
C14 C13 C18 O4 177.6(3) . . . . ?
O3 C13 C18 C17 -175.1(3) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
C2 N1 C1 O1 -175.8(2) . . . . ?
C20 N1 C1 O1 -3.1(4) . . . . ?
C2 N1 C1 C8 5.3(2) . . . . ?
C20 N1 C1 C8 177.95(19) . . . . ?
O2 C8 C1 O1 53.4(3) . . . . ?
C7 C8 C1 O1 176.3(2) . . . . ?
C9 C8 C1 O1 -63.4(3) . . . . ?
O2 C8 C1 N1 -127.62(18) . . . . ?
C7 C8 C1 N1 -4.7(2) . . . . ?
C9 C8 C1 N1 115.51(18) . . . . ?
C11 C10 N2 N3 0.1(2) . . . . ?
C11 C10 N2 C9 178.72(18) . . . . ?
C8 C9 N2 C10 -78.3(3) . . . . ?
C8 C9 N2 N3 100.2(2) . . . . ?
C10 N2 N3 N4 0.0(2) . . . . ?
C9 N2 N3 N4 -178.79(16) . . . . ?
N2 N3 N4 C11 -0.1(2) . . . . ?
C10 C11 N4 N3 0.1(2) . . . . ?
C12 C11 N4 N3 -178.38(19) . . . . ?
C14 C13 O3 C12 114.9(3) . . . . ?
C18 C13 O3 C12 -70.1(3) . . . . ?
C11 C12 O3 C13 -73.1(3) . . . . ?
C17 C18 O4 C19 -0.9(5) . . . . ?
C13 C18 O4 C19 -178.6(3) . . . . ?

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
O2 H1O N4 0.81(3) 2.09(3) 2.882(2) 165(3) 4_566

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.043


