# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_D43ZB66_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2096537'
loop_
_audit_author_name
_audit_author_address
'Merce Font Bardia '
;Barcelona University
Spain
;
_audit_update_record             
;
2021-07-14 deposited with the CCDC.	2022-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 Cl N O'
_chemical_formula_sum            'C12 H20 Cl N O'
_chemical_formula_weight         229.74

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.4389(15)
_cell_length_b                   16.182(3)
_cell_length_c                   8.8628(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.763(7)
_cell_angle_gamma                90
_cell_volume                     1209.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1998
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      24.10

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4710
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18662
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_av_R_equivalents  0.1559
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.517
_diffrn_reflns_theta_max         26.420
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2480
_reflns_number_gt                1693
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0122P)²+1.7681P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0052(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2480
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1043
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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 0.24300(10) 0.60506(5) 0.45996(9) 0.0283(2) Uani 1 1 d . . . . .
O1 O 0.1406(2) 0.43481(13) 0.3309(2) 0.0227(5) Uani 1 1 d . . . . .
N1 N 0.2823(3) 0.37360(14) 0.5291(3) 0.0159(6) Uani 1 1 d . . . . .
C1 C 0.2065(3) 0.43645(19) 0.4569(3) 0.0182(7) Uani 1 1 d . . . . .
C2 C 0.2124(4) 0.51116(18) 0.5618(3) 0.0178(7) Uani 1 1 d . . . . .
H2 H 0.110414 0.514989 0.615983 0.021 Uiso 1 1 calc R U . . .
C3 C 0.3460(3) 0.49086(17) 0.6748(3) 0.0159(6) Uani 1 1 d . . . . .
H3 H 0.448629 0.502417 0.625428 0.019 Uiso 1 1 calc R U . . .
C4 C 0.3478(4) 0.53640(18) 0.8252(3) 0.0210(7) Uani 1 1 d . . . . .
H4A H 0.332216 0.596144 0.805741 0.025 Uiso 1 1 calc R U . . .
H4B H 0.453303 0.529334 0.875421 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2213(4) 0.50688(19) 0.9318(3) 0.0233(7) Uani 1 1 d . . . . .
H5A H 0.237448 0.533949 1.031222 0.028 Uiso 1 1 calc R U . . .
H5B H 0.115219 0.522772 0.890727 0.028 Uiso 1 1 calc R U . . .
C6 C 0.2288(4) 0.41381(18) 0.9513(3) 0.0207(7) Uani 1 1 d . . . . .
H6A H 0.147475 0.395900 1.022471 0.025 Uiso 1 1 calc R U . . .
H6B H 0.334160 0.397872 0.994067 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2002(4) 0.37101(18) 0.7991(3) 0.0192(7) Uani 1 1 d . . . . .
H7A H 0.094092 0.386364 0.757256 0.023 Uiso 1 1 calc R U . . .
H7B H 0.202324 0.310352 0.813532 0.023 Uiso 1 1 calc R U . . .
C8 C 0.3275(3) 0.39603(18) 0.6871(3) 0.0156(6) Uani 1 1 d . . . . .
H8 H 0.431505 0.370181 0.716811 0.019 Uiso 1 1 calc R U . . .
C9 C 0.2868(4) 0.28750(18) 0.4691(3) 0.0181(7) Uani 1 1 d . . . . .
C10 C 0.3955(4) 0.23402(18) 0.5693(3) 0.0223(7) Uani 1 1 d . . . . .
H10A H 0.399986 0.178048 0.527421 0.033 Uiso 1 1 calc R U . . .
H10B H 0.354034 0.231710 0.671307 0.033 Uiso 1 1 calc R U . . .
H10C H 0.502202 0.257945 0.573545 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1203(4) 0.2512(2) 0.4608(3) 0.0232(7) Uani 1 1 d . . . . .
H11A H 0.051037 0.286964 0.398548 0.035 Uiso 1 1 calc R U . . .
H11B H 0.079028 0.247383 0.562684 0.035 Uiso 1 1 calc R U . . .
H11C H 0.123652 0.195970 0.415704 0.035 Uiso 1 1 calc R U . . .
C12 C 0.3569(4) 0.2899(2) 0.3112(3) 0.0248(7) Uani 1 1 d . . . . .
H12A H 0.363617 0.233547 0.271362 0.037 Uiso 1 1 calc R U . . .
H12B H 0.463179 0.314284 0.317816 0.037 Uiso 1 1 calc R U . . .
H12C H 0.288644 0.323330 0.243858 0.037 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 C2 1.790(3) . ?
O1 C1 1.233(3) . ?
N1 C1 1.352(4) . ?
N1 C8 1.485(3) . ?
N1 C9 1.492(4) . ?
C1 C2 1.525(4) . ?
C2 C3 1.520(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.523(4) . ?
C3 C8 1.547(4) . ?
C3 H3 1.0000 . ?
C4 C5 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.517(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.528(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.540(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8 1.0000 . ?
C9 C11 1.523(4) . ?
C9 C10 1.526(4) . ?
C9 C12 1.536(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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 C8 111.5(2) . . ?
C1 N1 C9 123.4(2) . . ?
C8 N1 C9 123.8(2) . . ?
O1 C1 N1 127.3(3) . . ?
O1 C1 C2 125.1(3) . . ?
N1 C1 C2 107.6(2) . . ?
C3 C2 C1 103.9(2) . . ?
C3 C2 Cl1 113.6(2) . . ?
C1 C2 Cl1 111.6(2) . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
Cl1 C2 H2 109.2 . . ?
C2 C3 C4 117.3(2) . . ?
C2 C3 C8 100.8(2) . . ?
C4 C3 C8 114.6(2) . . ?
C2 C3 H3 107.9 . . ?
C4 C3 H3 107.9 . . ?
C8 C3 H3 107.9 . . ?
C3 C4 C5 113.7(2) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 110.8(3) . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 110.1(2) . . ?
C5 C6 H6A 109.6 . . ?
C7 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C7 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C6 C7 C8 110.8(2) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 C7 112.3(2) . . ?
N1 C8 C3 101.5(2) . . ?
C7 C8 C3 112.3(2) . . ?
N1 C8 H8 110.1 . . ?
C7 C8 H8 110.1 . . ?
C3 C8 H8 110.1 . . ?
N1 C9 C11 110.1(2) . . ?
N1 C9 C10 110.1(2) . . ?
C11 C9 C10 110.3(3) . . ?
N1 C9 C12 108.4(2) . . ?
C11 C9 C12 110.3(2) . . ?
C10 C9 C12 107.6(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.081

