# 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 2024

####################################################################### 
# 
# 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_compound3a
_database_code_depnum_ccdc_archive 'CCDC 2308996'
loop_
_audit_author_name
_audit_author_address
'MALLI M.BHANUCHANDRA'
;Central University of Rajasthan 
India
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        3a
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 N2 O'
_chemical_formula_weight         236.27

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/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                   10.8378(11)
_cell_length_b                   7.4709(7)
_cell_length_c                   15.5056(15)
_cell_angle_alpha                90
_cell_angle_beta                 103.094(3)
_cell_angle_gamma                90
_cell_volume                     1222.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    7065
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      25.48

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.586
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.953
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_process_details   'SADABS, Bruker 2016'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  
'Bruker axs kappa apex3 PHOTON II Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36266
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0836
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.042
_diffrn_reflns_theta_max         25.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2315
_reflns_number_gt                1862
_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       'APEX3(Bruker, 2016)'
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1013P)²+0.4108P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2315
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1826
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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
C1 C 0.1580(2) 0.5808(3) 0.30416(15) 0.0294(6) Uani 1 1 d . . . . .
C2 C 0.2339(2) 0.5318(3) 0.38926(15) 0.0320(6) Uani 1 1 d . . . . .
C3 C 0.3416(2) 0.6259(4) 0.42229(16) 0.0374(6) Uani 1 1 d . . . . .
H3 H 0.390474 0.596257 0.477860 0.045 Uiso 1 1 calc R U . . .
C4 C 0.3814(2) 0.7670(3) 0.37468(17) 0.0363(6) Uani 1 1 d . . . . .
C5 C 0.4938(3) 0.8656(4) 0.4054(2) 0.0517(8) Uani 1 1 d . . . . .
H5 H 0.546385 0.836893 0.459840 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5265(3) 1.0014(5) 0.3571(2) 0.0608(9) Uani 1 1 d . . . . .
H6 H 0.600568 1.065599 0.378705 0.073 Uiso 1 1 calc R U . . .
C7 C 0.4488(3) 1.0451(4) 0.2748(2) 0.0550(8) Uani 1 1 d . . . . .
H7 H 0.471401 1.139099 0.242168 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3400(3) 0.9510(4) 0.24167(18) 0.0412(7) Uani 1 1 d . . . . .
H8 H 0.289453 0.979618 0.186520 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3058(2) 0.8123(3) 0.29131(16) 0.0316(6) Uani 1 1 d . . . . .
C10 C 0.1942(2) 0.3791(3) 0.43877(15) 0.0321(6) Uani 1 1 d . . . . .
C11 C 0.2015(3) 0.2044(4) 0.40981(18) 0.0397(6) Uani 1 1 d . . . . .
H11 H 0.225320 0.182618 0.356798 0.048 Uiso 1 1 calc R U . . .
C12 C 0.1736(3) 0.0631(4) 0.4593(2) 0.0456(7) Uani 1 1 d . . . . .
H12 H 0.177965 -0.053392 0.439095 0.055 Uiso 1 1 calc R U . . .
C13 C 0.1394(3) 0.0928(4) 0.53851(19) 0.0479(7) Uani 1 1 d . . . . .
H13 H 0.122841 -0.003023 0.572454 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1300(3) 0.2651(4) 0.5666(2) 0.0542(8) Uani 1 1 d . . . . .
H14 H 0.105214 0.285953 0.619380 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1571(3) 0.4085(4) 0.51743(17) 0.0435(7) Uani 1 1 d . . . . .
H15 H 0.150433 0.524829 0.537232 0.052 Uiso 1 1 calc R U . . .
N1 N 0.19467(18) 0.7169(3) 0.25892(12) 0.0284(5) Uani 1 1 d . . . . .
N2 N 0.0493(2) 0.5016(3) 0.26575(14) 0.0416(6) Uani 1 1 d . . . . .
H2A H 0.007235 0.538302 0.215011 0.050 Uiso 1 1 calc R U . . .
H2B H 0.021301 0.413855 0.291681 0.050 Uiso 1 1 calc R U . . .
O1 O 0.12090(17) 0.7607(2) 0.18068(11) 0.0391(5) 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 N2 1.331(3) . ?
C1 N1 1.346(3) . ?
C1 C2 1.436(3) . ?
C2 C3 1.359(3) . ?
C2 C10 1.492(3) . ?
C3 C4 1.409(4) . ?
C3 H3 0.9300 . ?
C4 C9 1.406(3) . ?
C4 C5 1.411(4) . ?
C5 C6 1.355(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.399(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.369(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.392(3) . ?
C10 C15 1.385(4) . ?
C10 C11 1.388(4) . ?
C11 C12 1.378(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N1 O1 1.334(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?

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
N2 C1 N1 116.0(2) . . ?
N2 C1 C2 124.2(2) . . ?
N1 C1 C2 119.7(2) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C10 121.7(2) . . ?
C1 C2 C10 119.7(2) . . ?
C2 C3 C4 121.9(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C3 118.6(2) . . ?
C9 C4 C5 117.6(3) . . ?
C3 C4 C5 123.8(2) . . ?
C6 C5 C4 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
C8 C9 N1 120.0(2) . . ?
C8 C9 C4 121.1(2) . . ?
N1 C9 C4 119.0(2) . . ?
C15 C10 C11 118.9(2) . . ?
C15 C10 C2 120.4(2) . . ?
C11 C10 C2 120.5(2) . . ?
C12 C11 C10 120.3(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C10 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O1 N1 C1 118.18(19) . . ?
O1 N1 C9 119.62(19) . . ?
C1 N1 C9 122.20(19) . . ?
C1 N2 H2A 120.0 . . ?
C1 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?

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
N2 C1 C2 C3 -178.5(2) . . . . ?
N1 C1 C2 C3 0.3(3) . . . . ?
N2 C1 C2 C10 2.1(4) . . . . ?
N1 C1 C2 C10 -179.1(2) . . . . ?
C1 C2 C3 C4 -1.2(4) . . . . ?
C10 C2 C3 C4 178.2(2) . . . . ?
C2 C3 C4 C9 0.9(4) . . . . ?
C2 C3 C4 C5 -178.6(3) . . . . ?
C9 C4 C5 C6 1.2(4) . . . . ?
C3 C4 C5 C6 -179.3(3) . . . . ?
C4 C5 C6 C7 -0.6(5) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 N1 179.2(2) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
C3 C4 C9 C8 179.6(2) . . . . ?
C5 C4 C9 C8 -0.9(4) . . . . ?
C3 C4 C9 N1 0.2(4) . . . . ?
C5 C4 C9 N1 179.7(2) . . . . ?
C3 C2 C10 C15 67.2(3) . . . . ?
C1 C2 C10 C15 -113.4(3) . . . . ?
C3 C2 C10 C11 -108.6(3) . . . . ?
C1 C2 C10 C11 70.8(3) . . . . ?
C15 C10 C11 C12 -0.7(4) . . . . ?
C2 C10 C11 C12 175.2(2) . . . . ?
C10 C11 C12 C13 -0.7(4) . . . . ?
C11 C12 C13 C14 1.7(4) . . . . ?
C12 C13 C14 C15 -1.4(5) . . . . ?
C13 C14 C15 C10 0.0(4) . . . . ?
C11 C10 C15 C14 1.0(4) . . . . ?
C2 C10 C15 C14 -174.9(2) . . . . ?
N2 C1 N1 O1 -0.1(3) . . . . ?
C2 C1 N1 O1 -179.0(2) . . . . ?
N2 C1 N1 C9 179.7(2) . . . . ?
C2 C1 N1 C9 0.8(3) . . . . ?
C8 C9 N1 O1 -0.7(3) . . . . ?
C4 C9 N1 O1 178.8(2) . . . . ?
C8 C9 N1 C1 179.5(2) . . . . ?
C4 C9 N1 C1 -1.0(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
_geom_hbond_publ_flag
N2 H2B O1 0.86 2.04 2.834(3) 152.8 2_545 yes

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.065



####################################################################### 
# 
# 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_compound3ia
_database_code_depnum_ccdc_archive 'CCDC 2308997'
loop_
_audit_author_name
_audit_author_address
'MALLI M.BHANUCHANDRA'
;Central University of Rajasthan 
India
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2024-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        3ia
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 Cl N2 O'
_chemical_formula_weight         346.80

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

_cell_length_a                   7.2658(2)
_cell_length_b                   7.9217(2)
_cell_length_c                   29.7691(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1713.43(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    299(2)
_cell_measurement_reflns_used    9941
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.06

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.053
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7113
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      299(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            52147
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.661
_diffrn_reflns_theta_max         27.112
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3787
_reflns_number_gt                3707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.716
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_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)+(0.0373P)²+0.4997P] 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 1473 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(12)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3787
_refine_ls_number_parameters     232
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0894
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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
C1 C 0.9352(4) 0.2620(3) 0.56049(8) 0.0371(5) Uani 1 1 d . . . . .
C2 C 1.0781(4) 0.2086(3) 0.58858(9) 0.0411(6) Uani 1 1 d . . . . .
H2 H 1.151537 0.117470 0.580402 0.049 Uiso 1 1 calc R U . . .
C3 C 1.1089(4) 0.2916(3) 0.62828(9) 0.0385(5) Uani 1 1 d . . . . .
H3 H 1.203180 0.256924 0.647285 0.046 Uiso 1 1 calc R U . . .
C4 C 0.9971(3) 0.4294(3) 0.64007(8) 0.0305(5) Uani 1 1 d . . . . .
C5 C 0.9308(3) 0.6483(3) 0.69288(7) 0.0299(4) Uani 1 1 d . . . . .
C6 C 0.7825(3) 0.7066(3) 0.66495(8) 0.0294(5) Uani 1 1 d . . . . .
C7 C 0.7434(3) 0.6260(3) 0.62552(7) 0.0295(5) Uani 1 1 d . . . . .
C8 C 0.8522(3) 0.4825(3) 0.61218(8) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.8237(4) 0.3946(3) 0.57149(8) 0.0349(5) Uani 1 1 d . . . . .
H9 H 0.729295 0.426964 0.552223 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6757(3) 0.8579(3) 0.68000(7) 0.0303(5) Uani 1 1 d . . . . .
C11 C 0.4934(4) 0.8410(4) 0.69382(8) 0.0398(5) Uani 1 1 d . . . . .
H11 H 0.438635 0.734911 0.694757 0.048 Uiso 1 1 calc R U . . .
C12 C 0.3942(4) 0.9825(4) 0.70611(10) 0.0512(7) Uani 1 1 d . . . . .
H12 H 0.272762 0.970770 0.715448 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4729(4) 1.1407(4) 0.70473(9) 0.0475(7) Uani 1 1 d . . . . .
H13 H 0.404981 1.235088 0.713059 0.057 Uiso 1 1 calc R U . . .
C14 C 0.6533(4) 1.1580(4) 0.69091(9) 0.0463(6) Uani 1 1 d . . . . .
H14 H 0.706598 1.264642 0.689634 0.056 Uiso 1 1 calc R U . . .
C15 C 0.7550(4) 1.0172(3) 0.67895(9) 0.0389(5) Uani 1 1 d . . . . .
H15 H 0.877118 1.029488 0.670162 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5931(3) 0.6887(3) 0.59545(7) 0.0310(5) Uani 1 1 d . . . . .
C17 C 0.4284(4) 0.6037(4) 0.59220(10) 0.0489(7) Uani 1 1 d . . . . .
H17 H 0.410216 0.505383 0.608697 0.059 Uiso 1 1 calc R U . . .
C18 C 0.2891(4) 0.6636(5) 0.56445(10) 0.0561(8) Uani 1 1 d . . . . .
H18 H 0.178482 0.605059 0.562354 0.067 Uiso 1 1 calc R U . . .
C19 C 0.3143(4) 0.8084(4) 0.54023(10) 0.0507(7) Uani 1 1 d . . . . .
H19 H 0.220596 0.849331 0.521953 0.061 Uiso 1 1 calc R U . . .
C20 C 0.4782(5) 0.8929(4) 0.54302(11) 0.0574(8) Uani 1 1 d . . . . .
H20 H 0.496128 0.990347 0.526180 0.069 Uiso 1 1 calc R U . . .
C21 C 0.6175(4) 0.8345(4) 0.57071(9) 0.0474(6) Uani 1 1 d . . . . .
H21 H 0.727847 0.893572 0.572645 0.057 Uiso 1 1 calc R U . . .
N1 N 1.0314(3) 0.5141(2) 0.67999(7) 0.0313(4) Uani 1 1 d . . . . .
N2 N 0.9789(3) 0.7180(3) 0.73202(7) 0.0395(5) Uani 1 1 d D . . . .
H2A H 0.914(4) 0.800(3) 0.7446(10) 0.047 Uiso 1 1 d D U . . .
H2B H 1.068(4) 0.668(4) 0.7450(10) 0.047 Uiso 1 1 d D U . . .
O1 O 1.1682(2) 0.4637(2) 0.70676(6) 0.0404(4) Uani 1 1 d . . . . .
Cl1 Cl 0.89960(11) 0.15457(9) 0.51006(2) 0.05032(19) 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 C9 1.367(4) . ?
C1 C2 1.398(4) . ?
C1 Cl1 1.745(2) . ?
C2 C3 1.371(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.405(3) . ?
C3 H3 0.9300 . ?
C4 N1 1.387(3) . ?
C4 C8 1.405(3) . ?
C5 N2 1.336(3) . ?
C5 N1 1.346(3) . ?
C5 C6 1.437(3) . ?
C6 C7 1.366(3) . ?
C6 C10 1.497(3) . ?
C7 C8 1.441(3) . ?
C7 C16 1.497(3) . ?
C8 C9 1.412(3) . ?
C9 H9 0.9300 . ?
C10 C15 1.388(4) . ?
C10 C11 1.394(3) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.376(4) . ?
C16 C21 1.381(3) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.367(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 O1 1.335(2) . ?
N2 H2A 0.89(2) . ?
N2 H2B 0.85(2) . ?

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 C1 C2 122.0(2) . . ?
C9 C1 Cl1 119.5(2) . . ?
C2 C1 Cl1 118.49(19) . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
N1 C4 C8 119.7(2) . . ?
N1 C4 C3 119.1(2) . . ?
C8 C4 C3 121.2(2) . . ?
N2 C5 N1 115.7(2) . . ?
N2 C5 C6 124.6(2) . . ?
N1 C5 C6 119.7(2) . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 C10 121.6(2) . . ?
C5 C6 C10 118.2(2) . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 C16 120.7(2) . . ?
C8 C7 C16 119.8(2) . . ?
C4 C8 C9 118.0(2) . . ?
C4 C8 C7 119.0(2) . . ?
C9 C8 C7 123.0(2) . . ?
C1 C9 C8 119.8(2) . . ?
C1 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C15 C10 C11 119.2(2) . . ?
C15 C10 C6 120.4(2) . . ?
C11 C10 C6 120.3(2) . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
C17 C16 C21 118.9(2) . . ?
C17 C16 C7 120.9(2) . . ?
C21 C16 C7 120.2(2) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.7(3) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C19 C20 C21 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 120.2(3) . . ?
C16 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
O1 N1 C5 118.03(19) . . ?
O1 N1 C4 120.05(19) . . ?
C5 N1 C4 121.92(19) . . ?
C5 N2 H2A 122(2) . . ?
C5 N2 H2B 114(2) . . ?
H2A N2 H2B 124(3) . . ?

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
C9 C1 C2 C3 -0.4(4) . . . . ?
Cl1 C1 C2 C3 179.8(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 N1 -179.0(2) . . . . ?
C2 C3 C4 C8 0.9(4) . . . . ?
N2 C5 C6 C7 -179.6(2) . . . . ?
N1 C5 C6 C7 0.2(3) . . . . ?
N2 C5 C6 C10 1.2(3) . . . . ?
N1 C5 C6 C10 -179.0(2) . . . . ?
C5 C6 C7 C8 -0.1(3) . . . . ?
C10 C6 C7 C8 179.0(2) . . . . ?
C5 C6 C7 C16 -178.1(2) . . . . ?
C10 C6 C7 C16 1.1(3) . . . . ?
N1 C4 C8 C9 179.0(2) . . . . ?
C3 C4 C8 C9 -0.9(3) . . . . ?
N1 C4 C8 C7 0.8(3) . . . . ?
C3 C4 C8 C7 -179.1(2) . . . . ?
C6 C7 C8 C4 -0.3(3) . . . . ?
C16 C7 C8 C4 177.6(2) . . . . ?
C6 C7 C8 C9 -178.4(2) . . . . ?
C16 C7 C8 C9 -0.5(3) . . . . ?
C2 C1 C9 C8 0.4(4) . . . . ?
Cl1 C1 C9 C8 -179.78(19) . . . . ?
C4 C8 C9 C1 0.3(3) . . . . ?
C7 C8 C9 C1 178.4(2) . . . . ?
C7 C6 C10 C15 -108.0(3) . . . . ?
C5 C6 C10 C15 71.1(3) . . . . ?
C7 C6 C10 C11 69.8(3) . . . . ?
C5 C6 C10 C11 -111.0(2) . . . . ?
C15 C10 C11 C12 0.2(4) . . . . ?
C6 C10 C11 C12 -177.7(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 -0.7(4) . . . . ?
C13 C14 C15 C10 1.1(4) . . . . ?
C11 C10 C15 C14 -0.9(4) . . . . ?
C6 C10 C15 C14 177.0(2) . . . . ?
C6 C7 C16 C17 -106.4(3) . . . . ?
C8 C7 C16 C17 75.7(3) . . . . ?
C6 C7 C16 C21 73.1(3) . . . . ?
C8 C7 C16 C21 -104.9(3) . . . . ?
C21 C16 C17 C18 0.0(4) . . . . ?
C7 C16 C17 C18 179.5(3) . . . . ?
C16 C17 C18 C19 -0.3(5) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C18 C19 C20 C21 -1.1(5) . . . . ?
C17 C16 C21 C20 -0.3(4) . . . . ?
C7 C16 C21 C20 -179.7(3) . . . . ?
C19 C20 C21 C16 0.8(5) . . . . ?
N2 C5 N1 O1 -0.3(3) . . . . ?
C6 C5 N1 O1 179.91(19) . . . . ?
N2 C5 N1 C4 -179.9(2) . . . . ?
C6 C5 N1 C4 0.3(3) . . . . ?
C8 C4 N1 O1 179.62(19) . . . . ?
C3 C4 N1 O1 -0.5(3) . . . . ?
C8 C4 N1 C5 -0.8(3) . . . . ?
C3 C4 N1 C5 179.1(2) . . . . ?

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
_geom_hbond_publ_flag
N2 H2A O1 0.89(2) 2.03(2) 2.873(3) 158(3) 3_756 yes
N2 H2B O1 0.85(2) 2.11(3) 2.552(3) 112(2) . yes

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.035



