# 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_anb050
_database_code_depnum_ccdc_archive 'CCDC 2193379'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Gontard'
;Sorbonne Universite, Paris
France
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2023-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_moiety         'C14 H11 N2 O, Cl, H2 O'
_chemical_formula_sum            'C14 H13 Cl N2 O2'
_chemical_formula_weight         276.71

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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, 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                   7.6114(4)
_cell_length_b                   15.1521(7)
_cell_length_c                   21.9238(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2528.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    6230
_cell_measurement_theta_min      4.04
_cell_measurement_theta_max      67.82

_exptl_crystal_description       needle
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    orange
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             1152
_exptl_absorpt_coefficient_mu    2.677
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.497
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_process_details   
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         micro-source
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            16493
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.033
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_full        66.500
_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 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2218
_reflns_number_gt                1981
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 2012)'
_computing_publication_material  'WinGX (Farrugia, 2012)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0484P)²+1.0132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0881
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.042

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 0.52929(6) 0.60616(3) 0.16546(2) 0.03890(15) Uani 1 1 d . . . . .
O1 O 0.04924(14) 0.89979(6) 0.53164(5) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.65235(19) 0.53278(9) 0.28974(6) 0.0471(3) Uani 1 1 d G . . . .
H2A H 0.624925 0.555327 0.249952 0.057 Uiso 1 1 d G U . . .
H2B H 0.765756 0.557010 0.299096 0.057 Uiso 1 1 d G U . . .
N1 N 0.11291(16) 0.94576(8) 0.43552(5) 0.0237(3) Uani 1 1 d . . . . .
H1 H 0.066197 0.997050 0.445090 0.028 Uiso 1 1 calc R U . . .
N2 N 0.37447(15) 0.71951(7) 0.39234(5) 0.0201(3) Uani 1 1 d . . . . .
H2C H 0.399818 0.680737 0.420898 0.024 Uiso 1 1 calc R U . . .
C1 C 0.12027(18) 0.88184(9) 0.48110(6) 0.0201(3) Uani 1 1 d . . . . .
C2 C 0.20660(18) 0.80166(9) 0.46643(6) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.27595(18) 0.79264(9) 0.40815(6) 0.0193(3) Uani 1 1 d . . . . .
C4 C 0.25454(19) 0.85791(9) 0.36205(6) 0.0224(3) Uani 1 1 d . . . . .
C5 C 0.1705(2) 0.93564(10) 0.37894(7) 0.0258(3) Uani 1 1 d . . . . .
H5 H 0.154363 0.981477 0.349905 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3184(2) 0.84256(11) 0.30236(7) 0.0277(3) Uani 1 1 d . . . . .
H6 H 0.302532 0.885841 0.271490 0.033 Uiso 1 1 calc R U . . .
C7 C 0.4029(2) 0.76529(11) 0.28926(7) 0.0293(4) Uani 1 1 d . . . . .
H7 H 0.440858 0.752761 0.248900 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4324(2) 0.70503(10) 0.33648(7) 0.0260(3) Uani 1 1 d . . . . .
H8 H 0.495668 0.652350 0.328145 0.031 Uiso 1 1 calc R U . . .
C9 C 0.21332(17) 0.73045(9) 0.51316(6) 0.0194(3) Uani 1 1 d . . . . .
C10 C 0.28006(19) 0.74798(10) 0.57110(6) 0.0247(3) Uani 1 1 d . . . . .
H10 H 0.327423 0.804493 0.580146 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2773(2) 0.68294(12) 0.61548(7) 0.0331(4) Uani 1 1 d . . . . .
H11 H 0.323728 0.694998 0.654831 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2076(2) 0.60068(12) 0.60305(8) 0.0371(4) Uani 1 1 d . . . . .
H12 H 0.202821 0.556990 0.634089 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1450(2) 0.58222(10) 0.54536(8) 0.0323(4) Uani 1 1 d . . . . .
H13 H 0.099941 0.525176 0.536500 0.039 Uiso 1 1 calc R U . . .
C14 C 0.14735(19) 0.64649(10) 0.50015(7) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.104235 0.633368 0.460508 0.028 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
O1 C1 1.2624(18) . ?
N1 C5 1.3245(19) . ?
N1 C1 1.3928(18) . ?
N2 C8 1.3200(19) . ?
N2 C3 1.3820(18) . ?
C1 C2 1.418(2) . ?
C2 C3 1.389(2) . ?
C2 C9 1.4887(19) . ?
C3 C4 1.4236(19) . ?
C4 C5 1.391(2) . ?
C4 C6 1.415(2) . ?
C6 C7 1.366(2) . ?
C7 C8 1.399(2) . ?
C9 C10 1.394(2) . ?
C9 C14 1.397(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.382(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.390(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
C5 N1 C1 125.33(12) . . ?
C8 N2 C3 123.18(12) . . ?
O1 C1 N1 117.56(12) . . ?
O1 C1 C2 125.59(13) . . ?
N1 C1 C2 116.84(12) . . ?
C3 C2 C1 117.97(12) . . ?
C3 C2 C9 123.26(12) . . ?
C1 C2 C9 118.73(12) . . ?
N2 C3 C2 121.05(12) . . ?
N2 C3 C4 116.17(12) . . ?
C2 C3 C4 122.76(13) . . ?
C5 C4 C6 122.92(13) . . ?
C5 C4 C3 116.87(13) . . ?
C6 C4 C3 120.21(13) . . ?
N1 C5 C4 119.98(13) . . ?
C7 C6 C4 119.79(14) . . ?
C6 C7 C8 118.65(14) . . ?
N2 C8 C7 121.64(14) . . ?
C10 C9 C14 119.38(13) . . ?
C10 C9 C2 120.11(13) . . ?
C14 C9 C2 120.48(12) . . ?
C11 C10 C9 119.95(15) . . ?
C12 C11 C10 120.60(15) . . ?
C13 C12 C11 119.74(14) . . ?
C12 C13 C14 120.48(15) . . ?
C13 C14 C9 119.81(14) . . ?

