# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_2AD24
_database_code_depnum_ccdc_archive 'CCDC 2252526'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CDIFX ISCR CNRS Univ Rennes
France
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 04 juin 2021                                             #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 Cl N O'
_chemical_formula_sum            'C10 H10 Cl N O'
_chemical_formula_weight         195.64
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   10.4075(13)
_cell_length_b                   6.8598(8)
_cell_length_c                   12.7321(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.950(6)
_cell_angle_gamma                90
_cell_volume                     889.29(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1745
_cell_measurement_theta_min      2.8334
_cell_measurement_theta_max      27.4352
_cell_measurement_wavelength     0.710730


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      0.0818586
_diffrn_orient_matrix_UB_21      0.0525803
_diffrn_orient_matrix_UB_31      0.0133342
_diffrn_orient_matrix_UB_12      -0.0669256
_diffrn_orient_matrix_UB_22      0.1178187
_diffrn_orient_matrix_UB_32      -0.0537339
_diffrn_orient_matrix_UB_13      -0.0102692
_diffrn_orient_matrix_UB_23      0.0281303
_diffrn_orient_matrix_UB_33      0.0744698


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.060
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             408
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_T_max  0.977

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

# Software                   : BIS 2014.5.0.0/23-May-2014 && APEX2_2014.11-0   #
# Number of scans            :        3                                        #
# Total number of frames     :      278                                        #
# Total length of scans      :   278.00 (deg.)                                 #
# Rotation speed             :    40.00 sec./deg.                              #
# Total exposition time      :      3 h   5.3 min.                             #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Omega   40.0  1.00    35.0   107  107.0   16.0   14.9  169.1  304.6 150.0 #
#  2 Omega   40.0  1.00    35.0    76   76.0   16.0  301.2  350.4   63.5 150.0 #
#  3 Omega   40.0  1.00    35.0    95   95.0  346.8  347.6   53.0  323.3 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'APEXII Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0404
_diffrn_reflns_av_r_equivalents  0.0273
_diffrn_reflns_number            5583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.271
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_reflns_number_total             2024
_reflns_number_gt                1555
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.

;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2020)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.0404P)²+0.0687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2024
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0930
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_restrained_S_all      1.121
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.057

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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 0.20350(17) 0.3008(2) 0.31215(14) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.25727(19) 0.2731(2) 0.41956(14) 0.0224(4) Uani 1 1 d . . . . .
H2 H 0.203091 0.262471 0.470866 0.027 Uiso 1 1 calc R U . . .
C3 C 0.39310(19) 0.2614(2) 0.45036(14) 0.0224(4) Uani 1 1 d . . . . .
H3 H 0.431700 0.243915 0.524170 0.027 Uiso 1 1 calc R U . . .
C4 C 0.47394(17) 0.2742(2) 0.37708(14) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.62048(18) 0.2550(3) 0.40815(14) 0.0238(4) Uani 1 1 d . . . . .
H5A H 0.645983 0.117537 0.400489 0.029 Uiso 1 1 calc R U . . .
H5B H 0.650880 0.293381 0.484199 0.029 Uiso 1 1 calc R U . . .
C6 C 0.68515(18) 0.3844(3) 0.33698(14) 0.0240(4) Uani 1 1 d . . . . .
H6A H 0.672877 0.522647 0.354892 0.029 Uiso 1 1 calc R U . . .
H6B H 0.780669 0.357490 0.351907 0.029 Uiso 1 1 calc R U . . .
C7 C 0.62970(18) 0.3524(2) 0.21967(14) 0.0212(4) Uani 1 1 d . . . . .
O8 O 0.69739(13) 0.36653(19) 0.15189(10) 0.0280(3) Uani 1 1 d . . . . .
N9 N 0.49846(14) 0.30947(19) 0.19206(11) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.43918(19) 0.2792(3) 0.07844(14) 0.0253(4) Uani 1 1 d . . . . .
H10A H 0.389347 0.395566 0.049867 0.038 Uiso 1 1 calc R U . . .
H10B H 0.380061 0.166568 0.071122 0.038 Uiso 1 1 calc R U . . .
H10C H 0.508472 0.255209 0.038335 0.038 Uiso 1 1 calc R U . . .
C11 C 0.41655(17) 0.3017(2) 0.26857(13) 0.0166(4) Uani 1 1 d . . . . .
C12 C 0.28083(17) 0.3170(2) 0.23605(13) 0.0174(4) Uani 1 1 d . . . . .
H12 H 0.241673 0.338169 0.162665 0.021 Uiso 1 1 calc R U . . .
Cl1 Cl 0.03318(4) 0.31479(6) 0.26990(4) 0.02514(15) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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 C2 1.379(2) . ?
C1 C12 1.386(2) . ?
C1 Cl1 1.7452(18) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.382(2) . ?
C3 H3 0.9500 . ?
C4 C11 1.400(2) . ?
C4 C5 1.500(2) . ?
C5 C6 1.521(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.502(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 O8 1.226(2) . ?
C7 N9 1.370(2) . ?
N9 C11 1.422(2) . ?
N9 C10 1.465(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.391(2) . ?
C12 H12 0.9500 . ?

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
C2 C1 C12 121.93(16) . . ?
C2 C1 Cl1 119.40(13) . . ?
C12 C1 Cl1 118.67(13) . . ?
C1 C2 C3 117.92(16) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C4 C3 C2 122.13(17) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C11 118.67(16) . . ?
C3 C4 C5 122.96(16) . . ?
C11 C4 C5 118.35(15) . . ?
C4 C5 C6 110.06(14) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.2 . . ?
C7 C6 C5 112.39(15) . . ?
C7 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
O8 C7 N9 121.62(16) . . ?
O8 C7 C6 122.02(17) . . ?
N9 C7 C6 116.36(15) . . ?
C7 N9 C11 122.65(14) . . ?
C7 N9 C10 118.52(14) . . ?
C11 N9 C10 118.77(14) . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C4 120.23(16) . . ?
C12 C11 N9 120.60(15) . . ?
C4 C11 N9 119.16(15) . . ?
C1 C12 C11 119.11(16) . . ?
C1 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?

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
C12 C1 C2 C3 -0.1(2) . . . . ?
Cl1 C1 C2 C3 179.58(13) . . . . ?
C1 C2 C3 C4 -0.8(3) . . . . ?
C2 C3 C4 C11 0.6(3) . . . . ?
C2 C3 C4 C5 -177.86(16) . . . . ?
C3 C4 C5 C6 -146.70(16) . . . . ?
C11 C4 C5 C6 34.8(2) . . . . ?
C4 C5 C6 C7 -51.5(2) . . . . ?
C5 C6 C7 O8 -146.43(17) . . . . ?
C5 C6 C7 N9 34.5(2) . . . . ?
O8 C7 N9 C11 -176.84(15) . . . . ?
C6 C7 N9 C11 2.2(2) . . . . ?
O8 C7 N9 C10 0.3(2) . . . . ?
C6 C7 N9 C10 179.30(15) . . . . ?
C3 C4 C11 C12 0.4(2) . . . . ?
C5 C4 C11 C12 178.94(15) . . . . ?
C3 C4 C11 N9 -178.20(15) . . . . ?
C5 C4 C11 N9 0.3(2) . . . . ?
C7 N9 C11 C12 160.32(15) . . . . ?
C10 N9 C11 C12 -16.8(2) . . . . ?
C7 N9 C11 C4 -21.1(2) . . . . ?
C10 N9 C11 C4 161.81(15) . . . . ?
C2 C1 C12 C11 1.1(2) . . . . ?
Cl1 C1 C12 C11 -178.60(12) . . . . ?
C4 C11 C12 C1 -1.2(2) . . . . ?
N9 C11 C12 C1 177.37(14) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


