# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_11e
_database_code_depnum_ccdc_archive 'CCDC 2220181'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2022-11-16 deposited with the CCDC.	2023-06-27 downloaded from the CCDC.
;
_audit_creation_date             2022-08-19
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Cl N2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O'
_chemical_formula_weight         260.71
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   6.7519(6)
_cell_length_b                   15.0413(13)
_cell_length_c                   24.732(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2511.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7965
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.26
_cell_measurement_theta_min      2.71
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            29777
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.708
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1741
_reflns_number_total             2194
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+1.5819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1169
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C13(H13)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.02583(11) 0.53275(5) 0.68575(3) 0.0822(4) Uani 1 1 d . . . . .
O1 O 0.7399(3) 0.39811(12) 0.53270(7) 0.0686(6) Uani 1 1 d . . . . .
N1 N 0.5975(3) 0.34287(12) 0.68913(7) 0.0468(5) Uani 1 1 d . . . . .
N2 N 0.7930(3) 0.32037(12) 0.61088(7) 0.0463(5) Uani 1 1 d . . . . .
C1 C 0.4768(3) 0.39942(13) 0.65953(8) 0.0405(5) Uani 1 1 d . . . . .
C2 C 0.3086(3) 0.43589(15) 0.68478(9) 0.0465(6) Uani 1 1 d . . . . .
H2 H 0.283518 0.425076 0.721163 0.056 Uiso 1 1 calc R U . . .
C3 C 0.1829(3) 0.48735(15) 0.65502(10) 0.0504(6) Uani 1 1 d . . . . .
C4 C 0.2145(4) 0.50536(16) 0.60047(10) 0.0554(6) Uani 1 1 d . . . . .
H4 H 0.124242 0.539262 0.580934 0.067 Uiso 1 1 calc R U . . .
C5 C 0.3809(4) 0.47220(14) 0.57619(9) 0.0526(6) Uani 1 1 d . . . . .
H5 H 0.405688 0.484850 0.540012 0.063 Uiso 1 1 calc R U . . .
C6 C 0.5138(3) 0.41946(14) 0.60530(8) 0.0431(5) Uani 1 1 d . . . . .
C7 C 0.6877(3) 0.38141(15) 0.57904(9) 0.0486(6) Uani 1 1 d . . . . .
C8 C 0.9501(3) 0.26967(16) 0.58195(10) 0.0555(6) Uani 1 1 d . . . . .
H8 H 1.017944 0.310776 0.557408 0.067 Uiso 1 1 calc R U . . .
C9 C 1.1030(4) 0.23261(18) 0.62099(12) 0.0708(8) Uani 1 1 d . . . . .
H9A H 1.193030 0.193721 0.601622 0.085 Uiso 1 1 calc R U . . .
H9B H 1.179759 0.281083 0.636167 0.085 Uiso 1 1 calc R U . . .
C10 C 1.0041(4) 0.18116(18) 0.66628(11) 0.0666(8) Uani 1 1 d . . . . .
H10A H 0.926423 0.132732 0.651415 0.080 Uiso 1 1 calc R U . . .
H10B H 1.103688 0.156204 0.690132 0.080 Uiso 1 1 calc R U . . .
C11 C 0.8717(4) 0.24374(18) 0.69744(10) 0.0639(7) Uani 1 1 d . . . . .
H11A H 0.785825 0.208522 0.720471 0.077 Uiso 1 1 calc R U . . .
H11B H 0.954250 0.279834 0.720853 0.077 Uiso 1 1 calc R U . . .
C12 C 0.7447(3) 0.30464(15) 0.66430(8) 0.0456(5) Uani 1 1 d . . . . .
C13 C 0.8613(4) 0.19628(18) 0.54839(10) 0.0629(7) Uani 1 1 d . . . . .
H13 H 0.946601 0.168464 0.524193 0.075 Uiso 1 1 calc R U . . .
C14 C 0.6820(5) 0.1673(2) 0.54904(11) 0.0757(9) Uani 1 1 d . . . . .
H14A H 0.589684 0.192409 0.572391 0.091 Uiso 1 1 calc R U . . .
H14B H 0.644691 0.121124 0.526165 0.091 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
Cl1 C3 1.741(2) . ?
O1 C7 1.225(3) . ?
N1 C1 1.387(3) . ?
N1 C12 1.302(3) . ?
N2 C7 1.403(3) . ?
N2 C8 1.489(3) . ?
N2 C12 1.381(3) . ?
C1 C2 1.407(3) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(3) . ?
C3 C4 1.392(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(3) . ?
C6 C7 1.459(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.520(4) . ?
C8 C13 1.506(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.516(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.510(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.499(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.287(4) . ?
C14 H14A 0.9300 . ?
C14 H14B 0.9300 . ?

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
C12 N1 C1 118.06(18) . . ?
C7 N2 C8 115.23(18) . . ?
C12 N2 C7 121.95(18) . . ?
C12 N2 C8 122.69(19) . . ?
N1 C1 C2 118.62(18) . . ?
N1 C1 C6 122.26(19) . . ?
C6 C1 C2 119.1(2) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 Cl1 119.38(18) . . ?
C2 C3 C4 122.5(2) . . ?
C4 C3 Cl1 118.08(18) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.7(2) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.5(2) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 120.1(2) . . ?
C1 C6 C7 119.1(2) . . ?
C5 C6 C7 120.69(19) . . ?
O1 C7 N2 120.9(2) . . ?
O1 C7 C6 124.6(2) . . ?
N2 C7 C6 114.51(18) . . ?
N2 C8 H8 107.9 . . ?
N2 C8 C9 111.5(2) . . ?
N2 C8 C13 110.90(19) . . ?
C9 C8 H8 107.9 . . ?
C13 C8 H8 107.9 . . ?
C13 C8 C9 110.6(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 110.9(2) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C9 C10 H10A 110.0 . . ?
C9 C10 H10B 110.0 . . ?
H10A C10 H10B 108.3 . . ?
C11 C10 C9 108.6(2) . . ?
C11 C10 H10A 110.0 . . ?
C11 C10 H10B 110.0 . . ?
C10 C11 H11A 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
C12 C11 C10 116.1(2) . . ?
C12 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
N1 C12 N2 123.8(2) . . ?
N1 C12 C11 116.6(2) . . ?
N2 C12 C11 119.5(2) . . ?
C8 C13 H13 116.0 . . ?
C14 C13 C8 128.1(2) . . ?
C14 C13 H13 116.0 . . ?
C13 C14 H14A 120.0 . . ?
C13 C14 H14B 120.0 . . ?
H14A C14 H14B 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
Cl1 C3 C4 C5 178.18(18) . . . . ?
N1 C1 C2 C3 -176.2(2) . . . . ?
N1 C1 C6 C5 175.83(19) . . . . ?
N1 C1 C6 C7 -1.5(3) . . . . ?
N2 C8 C9 C10 51.7(3) . . . . ?
N2 C8 C13 C14 -11.1(4) . . . . ?
C1 N1 C12 N2 3.1(3) . . . . ?
C1 N1 C12 C11 -179.8(2) . . . . ?
C1 C2 C3 Cl1 179.93(16) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 O1 -176.0(2) . . . . ?
C1 C6 C7 N2 5.6(3) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C1 C6 C7 -179.76(19) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
C3 C4 C5 C6 1.6(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 177.8(2) . . . . ?
C5 C6 C7 O1 6.7(3) . . . . ?
C5 C6 C7 N2 -171.69(19) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C7 N2 C8 C9 158.82(19) . . . . ?
C7 N2 C8 C13 -77.5(2) . . . . ?
C7 N2 C12 N1 1.5(3) . . . . ?
C7 N2 C12 C11 -175.5(2) . . . . ?
C8 N2 C7 O1 -8.3(3) . . . . ?
C8 N2 C7 C6 170.20(18) . . . . ?
C8 N2 C12 N1 -174.1(2) . . . . ?
C8 N2 C12 C11 8.9(3) . . . . ?
C8 C9 C10 C11 -61.6(3) . . . . ?
C9 C8 C13 C14 113.2(3) . . . . ?
C9 C10 C11 C12 44.7(3) . . . . ?
C10 C11 C12 N1 163.8(2) . . . . ?
C10 C11 C12 N2 -19.0(3) . . . . ?
C12 N1 C1 C2 175.26(19) . . . . ?
C12 N1 C1 C6 -3.1(3) . . . . ?
C12 N2 C7 O1 175.8(2) . . . . ?
C12 N2 C7 C6 -5.7(3) . . . . ?
C12 N2 C8 C9 -25.3(3) . . . . ?
C12 N2 C8 C13 98.4(2) . . . . ?
C13 C8 C9 C10 -72.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
