# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelx
_audit_block_doi                 10.5517/ccdc.csd.cc240qqm
_database_code_depnum_ccdc_archive 'CCDC 1966910'
loop_
_audit_author_name
_audit_author_address
'MD. Waseem Hussain'
;Indian Institute of Science Education and Research Bhopal
India
;
_audit_update_record             
;
2019-11-20 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H26 Cl N7 O'
_chemical_formula_weight         463.97

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      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                   8.6917(2)
_cell_length_b                   15.6895(5)
_cell_length_c                   17.8706(6)
_cell_angle_alpha                90
_cell_angle_beta                 101.494(2)
_cell_angle_gamma                90
_cell_volume                     2388.11(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4446
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      24.23

_exptl_crystal_description       rectangular
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    0.191
_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            27187
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.743
_diffrn_reflns_theta_max         30.741
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7340
_reflns_number_gt                4506
_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)+(0.0850P)²+1.0431P] 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_number_reflns         7340
_refine_ls_number_parameters     305
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1177
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_ref         0.1939
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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 0.57968(7) 0.45615(4) 0.63321(3) 0.03447(17) Uani 1 1 d . . . . .
N4 N -0.0310(2) 0.79808(12) 1.08457(10) 0.0283(4) Uani 1 1 d . . . . .
O3 O 0.7098(2) 0.94462(13) 0.00382(11) 0.0417(5) Uani 1 1 d . . . . .
H3B H 0.689(4) 0.964(2) 0.041(2) 0.072(12) Uiso 1 1 d . . . . .
H3C H 0.613001 0.946099 -0.038(2) 0.098(14) Uiso 1 1 d . . . . .
C3 C 0.8188(3) 0.57440(19) 1.02039(14) 0.0408(6) Uani 1 1 d . . . . .
H3 H 0.899319 0.535536 1.036612 0.049 Uiso 1 1 calc R U . . .
C26 C 0.6787(4) 0.5648(2) 1.04418(17) 0.0524(8) Uani 1 1 d . . . . .
H26 H 0.663974 0.518912 1.074968 0.063 Uiso 1 1 calc R U . . .
C5 C 0.5608(3) 0.62308(18) 1.02232(16) 0.0478(7) Uani 1 1 d . . . . .
H5 H 0.466050 0.616204 1.038256 0.057 Uiso 1 1 calc R U . . .
C6 C 0.5806(3) 0.69134(15) 0.97736(12) 0.0289(5) Uani 1 1 d . . . . .
N3 N 0.1061(2) 0.79095(13) 1.05661(10) 0.0315(4) Uani 1 1 d . . . . .
H3A H 0.182474 0.759006 1.078299 0.038 Uiso 1 1 calc R U . . .
C8 C -0.0337(3) 0.75098(15) 1.14391(13) 0.0317(5) Uani 1 1 d . . . . .
H8 H 0.055325 0.720330 1.166065 0.038 Uiso 1 1 calc R U . . .
C9 C -0.1745(3) 0.74544(15) 1.17632(13) 0.0316(5) Uani 1 1 d . . . . .
C10 C -0.1766(3) 0.68556(16) 1.23478(14) 0.0372(6) Uani 1 1 d . . . . .
H10 H -0.087245 0.653865 1.254333 0.045 Uiso 1 1 calc R U . . .
C11 C -0.3121(3) 0.67407(16) 1.26300(15) 0.0401(6) Uani 1 1 d . . . . .
H11 H -0.313659 0.634539 1.301611 0.048 Uiso 1 1 calc R U . . .
C12 C -0.4452(3) 0.72109(17) 1.23410(15) 0.0417(6) Uani 1 1 d . . . . .
H12 H -0.536562 0.712543 1.252766 0.050 Uiso 1 1 calc R U . . .
C18 C -0.2515(3) 1.12720(18) 0.70866(15) 0.0397(6) Uani 1 1 d . . . . .
H18 H -0.343532 1.156606 0.688909 0.048 Uiso 1 1 calc R U . . .
C19 C -0.1257(3) 1.13114(17) 0.67252(15) 0.0409(6) Uani 1 1 d . . . . .
H19 H -0.131828 1.163416 0.628369 0.049 Uiso 1 1 calc R U . . .
C20 C 0.0107(3) 1.08633(18) 0.70275(16) 0.0441(6) Uani 1 1 d . . . . .
H20 H 0.095409 1.088874 0.678173 0.053 Uiso 1 1 calc R U . . .
C2 C 0.8421(3) 0.63955(17) 0.97363(14) 0.0375(6) Uani 1 1 d . . . . .
H2 H 0.936470 0.644581 0.956994 0.045 Uiso 1 1 calc R U . . .
C1 C 0.7209(3) 0.69917(17) 0.95090(14) 0.0359(6) Uani 1 1 d . . . . .
H1 H 0.734001 0.743666 0.918357 0.043 Uiso 1 1 calc R U . . .
C14 C -0.3085(3) 0.79284(16) 1.14894(14) 0.0360(6) Uani 1 1 d . . . . .
H14 H -0.307593 0.833183 1.110904 0.043 Uiso 1 1 calc R U . . .
C13 C -0.4426(3) 0.78099(18) 1.17726(15) 0.0432(6) Uani 1 1 d . . . . .
H13 H -0.531801 0.813136 1.158342 0.052 Uiso 1 1 calc R U . . .
N7 N 0.2161(3) 0.61455(15) 0.10984(14) 0.0465(6) Uani 1 1 d . . . . .
C7 C 0.4603(3) 0.75724(15) 0.95484(13) 0.0319(5) Uani 1 1 d . . . . .
H7 H 0.471940 0.796360 0.917260 0.038 Uiso 1 1 calc R U . . .
N2 N 0.3405(2) 0.76201(12) 0.98566(10) 0.0282(4) Uani 1 1 d . . . . .
N1 N 0.2343(2) 0.82539(13) 0.95917(11) 0.0318(4) Uani 1 1 d . . . . .
H1A H 0.245739 0.856887 0.921278 0.038 Uiso 1 1 calc R U . . .
C27 C 0.1134(3) 0.83687(14) 0.99347(12) 0.0272(5) Uani 1 1 d . . . . .
N5 N 0.0012(2) 0.89247(12) 0.96783(10) 0.0303(4) Uani 1 1 d . . . . .
H5A H -0.074996 0.901761 0.990974 0.036 Uiso 1 1 calc R U . . .
N6 N 0.0140(2) 0.93570(12) 0.90007(10) 0.0272(4) Uani 1 1 d . . . . .
C15 C -0.0991(3) 0.98603(15) 0.87497(12) 0.0295(5) Uani 1 1 d . . . . .
H15 H -0.180199 0.992050 0.901540 0.035 Uiso 1 1 calc R U . . .
C16 C -0.1031(3) 1.03486(14) 0.80433(12) 0.0289(5) Uani 1 1 d . . . . .
C17 C -0.2400(3) 1.07873(16) 0.77519(14) 0.0337(5) Uani 1 1 d . . . . .
H17 H -0.324434 1.075971 0.799885 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0233(3) 1.03840(16) 0.76807(14) 0.0365(6) Uani 1 1 d . . . . .
H21 H 0.115275 1.008829 0.787565 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2963(3) 0.56165(16) 0.13871(14) 0.0341(5) Uani 1 1 d . . . . .
C24 C 0.4033(3) 0.49603(17) 0.17395(13) 0.0353(5) Uani 1 1 d . . . . .
H24A H 0.395566 0.447646 0.140532 0.053 Uiso 1 1 calc R U . . .
H24B H 0.376580 0.479222 0.221427 0.053 Uiso 1 1 calc R U . . .
H24C H 0.508705 0.517632 0.183314 0.053 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
N4 C8 1.297(3) . ?
N4 N3 1.385(2) . ?
O3 H3B 0.79(4) . ?
O3 H3C 1.00(2) . ?
C3 C2 1.361(4) . ?
C3 C26 1.376(4) . ?
C3 H3 0.9300 . ?
C26 C5 1.371(4) . ?
C26 H26 0.9300 . ?
C5 C6 1.370(3) . ?
C5 H5 0.9300 . ?
C6 C1 1.398(3) . ?
C6 C7 1.468(3) . ?
N3 C27 1.351(3) . ?
N3 H3A 0.8600 . ?
C8 C9 1.457(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.387(3) . ?
C9 C10 1.408(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C18 C19 1.378(4) . ?
C18 C17 1.398(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.392(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(3) . ?
C20 H20 0.9300 . ?
C2 C1 1.407(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C14 C13 1.373(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
N7 C25 1.139(3) . ?
C7 N2 1.274(3) . ?
C7 H7 0.9300 . ?
N2 N1 1.375(3) . ?
N1 C27 1.330(3) . ?
N1 H1A 0.8600 . ?
C27 N5 1.321(3) . ?
N5 N6 1.412(3) . ?
N5 H5A 0.8600 . ?
N6 C15 1.271(3) . ?
C15 C16 1.471(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C25 C24 1.445(4) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
C8 N4 N3 113.96(19) . . ?
H3B O3 H3C 109(3) . . ?
C2 C3 C26 121.4(3) . . ?
C2 C3 H3 119.3 . . ?
C26 C3 H3 119.3 . . ?
C5 C26 C3 119.7(3) . . ?
C5 C26 H26 120.1 . . ?
C3 C26 H26 120.1 . . ?
C26 C5 C6 121.0(3) . . ?
C26 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.1(2) . . ?
C5 C6 C7 123.1(2) . . ?
C1 C6 C7 117.8(2) . . ?
C27 N3 N4 116.44(19) . . ?
C27 N3 H3A 121.8 . . ?
N4 N3 H3A 121.8 . . ?
N4 C8 C9 120.8(2) . . ?
N4 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C14 C9 C10 119.0(2) . . ?
C14 C9 C8 122.7(2) . . ?
C10 C9 C8 118.1(2) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 120.0(2) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 119.3(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 121.6(2) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C3 C2 C1 118.8(2) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C14 C13 C12 120.0(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C7 C6 121.4(2) . . ?
N2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 N2 N1 116.38(19) . . ?
C27 N1 N2 118.49(19) . . ?
C27 N1 H1A 120.8 . . ?
N2 N1 H1A 120.8 . . ?
N5 C27 N1 121.8(2) . . ?
N5 C27 N3 119.18(19) . . ?
N1 C27 N3 119.1(2) . . ?
C27 N5 N6 115.82(17) . . ?
C27 N5 H5A 122.1 . . ?
N6 N5 H5A 122.1 . . ?
C15 N6 N5 114.41(18) . . ?
N6 C15 C16 120.7(2) . . ?
N6 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C21 120.5(2) . . ?
C17 C16 C15 117.0(2) . . ?
C21 C16 C15 122.5(2) . . ?
C16 C17 C18 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C20 C21 C16 118.9(2) . . ?
C20 C21 H21 120.5 . . ?
C16 C21 H21 120.5 . . ?
N7 C25 C24 177.6(3) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C25 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_refine_diff_density_max         0.748
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.068

