# Electronic Supplementary Material (ESI) for ChemComm.
# 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_trans-4bo
_database_code_depnum_ccdc_archive 'CCDC 2129406'
loop_
_audit_author_name
_audit_author_address
'Andrew White'
;Imperial College London
United Kingdom
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-02-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cl N O4'
_chemical_formula_sum            'C12 H12 Cl N O4'
_chemical_formula_weight         269.68

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

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

_cell_length_a                   9.0510(5)
_cell_length_b                   13.7353(8)
_cell_length_c                   10.1333(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.133(5)
_cell_angle_gamma                90
_cell_volume                     1247.08(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1018
_cell_measurement_theta_min      2.9610
_cell_measurement_theta_max      28.1280

_exptl_crystal_description       blocks
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.469
_exptl_crystal_size_mid          0.368
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    0.312
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            2093
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.714
_diffrn_reflns_theta_max         28.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.534
_diffrn_reflns_point_group_measured_fraction_full 0.659
_reflns_number_total             1620
_reflns_number_gt                1548
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.290
_reflns_Friedel_fraction_max     0.241
_reflns_Friedel_fraction_full    0.324

_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0344P)²+0.4324P] 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_abs_structure_details 
; 
 Flack x determined using 350 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.05(6)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1620
_refine_ls_number_parameters     165
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.080
_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
N1 N 0.2435(3) 0.34578(17) 0.2023(2) 0.0216(5) Uani 1 1 d . . . . .
C2 C 0.2505(3) 0.4520(2) 0.1875(3) 0.0214(6) Uani 1 1 d . . . . .
H2A H 0.176923 0.481879 0.116016 0.026 Uiso 1 1 calc R U . . .
C3 C 0.1876(3) 0.4065(2) 0.3034(3) 0.0232(6) Uani 1 1 d . . . . .
H3A H 0.251377 0.410174 0.392323 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3714(3) 0.2876(2) 0.2449(3) 0.0223(6) Uani 1 1 d . . . . .
C5 C 0.4892(3) 0.2793(2) 0.1708(3) 0.0258(7) Uani 1 1 d . . . . .
Cl5 Cl 0.49108(8) 0.34775(6) 0.02635(8) 0.0372(2) Uani 1 1 d . . . . .
C6 C 0.6094(3) 0.2182(2) 0.2120(3) 0.0322(7) Uani 1 1 d . . . . .
H6A H 0.689800 0.214162 0.161282 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6119(4) 0.1637(2) 0.3262(4) 0.0356(8) Uani 1 1 d . . . . .
H7A H 0.694377 0.122343 0.354930 0.043 Uiso 1 1 calc R U . . .
C8 C 0.4939(4) 0.1693(2) 0.3990(3) 0.0335(8) Uani 1 1 d . . . . .
H8A H 0.494532 0.130975 0.477079 0.040 Uiso 1 1 calc R U . . .
C9 C 0.3751(3) 0.2305(2) 0.3583(3) 0.0282(7) Uani 1 1 d . . . . .
H9A H 0.294487 0.233610 0.408880 0.034 Uiso 1 1 calc R U . . .
C10 C 0.3956(3) 0.5044(2) 0.2226(3) 0.0228(6) Uani 1 1 d . . . . .
O10 O 0.4887(2) 0.48398(15) 0.31462(19) 0.0284(5) Uani 1 1 d . . . . .
O11 O 0.4054(2) 0.57678(16) 0.1354(2) 0.0295(5) Uani 1 1 d . . . . .
C12 C 0.5444(4) 0.6309(3) 0.1549(4) 0.0459(10) Uani 1 1 d . . . . .
H12A H 0.558113 0.663879 0.071708 0.069 Uiso 1 1 calc R U . . .
H12B H 0.627634 0.586014 0.180609 0.069 Uiso 1 1 calc R U . . .
H12C H 0.541270 0.679354 0.225399 0.069 Uiso 1 1 calc R U . . .
C13 C 0.0217(3) 0.4064(2) 0.3039(3) 0.0257(7) Uani 1 1 d . . . . .
O13 O -0.0696(3) 0.3953(2) 0.2077(2) 0.0492(7) Uani 1 1 d . . . . .
O14 O -0.0066(2) 0.42134(17) 0.4265(2) 0.0303(5) Uani 1 1 d . . . . .
C15 C -0.1635(4) 0.4243(3) 0.4444(4) 0.0430(9) Uani 1 1 d . . . . .
H15A H -0.214128 0.476065 0.388804 0.064 Uiso 1 1 calc R U . . .
H15B H -0.171489 0.437248 0.538246 0.064 Uiso 1 1 calc R U . . .
H15C H -0.210268 0.361560 0.418279 0.064 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
N1 C4 1.423(4) . ?
N1 C3 1.465(4) . ?
N1 C2 1.469(4) . ?
C2 C10 1.495(4) . ?
C2 C3 1.511(4) . ?
C3 C13 1.502(4) . ?
C4 C9 1.388(4) . ?
C4 C5 1.393(4) . ?
C5 C6 1.390(4) . ?
C5 Cl5 1.742(3) . ?
C6 C7 1.376(5) . ?
C7 C8 1.384(5) . ?
C8 C9 1.381(5) . ?
C10 O10 1.199(3) . ?
C10 O11 1.341(4) . ?
O11 C12 1.450(4) . ?
C13 O13 1.195(4) . ?
C13 O14 1.320(4) . ?
O14 C15 1.458(4) . ?

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
C4 N1 C3 117.0(2) . . ?
C4 N1 C2 122.9(2) . . ?
C3 N1 C2 61.99(18) . . ?
N1 C2 C10 120.2(2) . . ?
N1 C2 C3 58.88(18) . . ?
C10 C2 C3 115.4(2) . . ?
N1 C3 C13 116.4(3) . . ?
N1 C3 C2 59.13(18) . . ?
C13 C3 C2 119.3(3) . . ?
C9 C4 C5 118.0(3) . . ?
C9 C4 N1 119.5(3) . . ?
C5 C4 N1 122.3(3) . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 Cl5 118.5(2) . . ?
C4 C5 Cl5 120.5(2) . . ?
C7 C6 C5 120.0(3) . . ?
C6 C7 C8 119.7(3) . . ?
C9 C8 C7 120.2(3) . . ?
C8 C9 C4 121.2(3) . . ?
O10 C10 O11 125.5(3) . . ?
O10 C10 C2 124.7(3) . . ?
O11 C10 C2 109.8(3) . . ?
C10 O11 C12 115.3(3) . . ?
O13 C13 O14 125.7(3) . . ?
O13 C13 C3 125.0(3) . . ?
O14 C13 C3 109.3(3) . . ?
C13 O14 C15 116.4(3) . . ?

_refine_diff_density_max         0.167
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042



#===END


