# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2082859'
loop_
_audit_author_name
_audit_author_address
'Yasunori Toda'
;Shinshu University
Japan
;
_audit_update_record             
;
2021-05-11 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 Cl N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         241.67
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.0808(12)
_cell_length_b                   10.5099(14)
_cell_length_c                   11.7960(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1125.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    69
_cell_measurement_theta_min      3.4208
_cell_measurement_theta_max      17.1842
_cell_measurement_temperature    93.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504

_exptl_absorpt_coefficient_mu    0.330
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      93.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13280
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0939
_diffrn_reflns_theta_min         2.60
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_full        27.99
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_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.
;

_reflns_number_total             2688
_reflns_number_gt                1219
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1527
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.1002
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_number_reflns         2688
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0308P)²+0.0000P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.181
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.017(2)
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(11)

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service v2010.11.0.0'
_computing_cell_refinement       'APEX2 v2010.11-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.94299(13) 0.28050(9) 0.34222(9) 0.0827(4) Uani d . 1 . .
O O1 0.6998(3) 0.8987(2) 0.2350(2) 0.0752(9) Uani d . 1 . .
H H1 0.7378 0.9501 0.1891 0.113 Uiso calc R 1 . .
O O2 0.6701(3) 1.0329(2) 0.4519(2) 0.0622(8) Uani d . 1 . .
O O3 0.7245(3) 0.9019(2) 0.5904(2) 0.0635(8) Uani d . 1 . .
N N1 0.5749(3) 0.8292(2) 0.4524(2) 0.0438(7) Uani d . 1 . .
C C1 0.8307(4) 0.4041(4) 0.3887(3) 0.0530(10) Uani d . 1 . .
C C2 0.7253(4) 0.3816(3) 0.4697(3) 0.0606(11) Uani d . 1 . .
H H2 0.7126 0.2987 0.5002 0.073 Uiso calc R 1 . .
C C3 0.6383(4) 0.4807(3) 0.5060(3) 0.0569(11) Uani d . 1 . .
H H3 0.565 0.4654 0.5618 0.068 Uiso calc R 1 . .
C C4 0.6554(4) 0.6030(3) 0.4626(3) 0.0457(9) Uani d . 1 . .
C C5 0.5565(4) 0.7072(3) 0.5085(3) 0.0535(9) Uani d . 1 . .
H H5A 0.4526 0.6799 0.5005 0.064 Uiso calc R 1 . .
H H5B 0.5767 0.718 0.5904 0.064 Uiso calc R 1 . .
C C6 0.4945(4) 0.8475(3) 0.3470(3) 0.0590(10) Uani d . 1 . .
H H6A 0.3914 0.8716 0.3639 0.071 Uiso calc R 1 . .
H H6B 0.4932 0.767 0.3035 0.071 Uiso calc R 1 . .
C C7 0.5666(4) 0.9503(3) 0.2775(3) 0.0580(10) Uani d . 1 . .
H H7 0.5008 0.9736 0.2127 0.07 Uiso calc R 1 . .
C C8 0.5907(4) 1.0639(3) 0.3500(3) 0.0653(11) Uani d . 1 . .
H H8A 0.6467 1.1284 0.3067 0.078 Uiso calc R 1 . .
H H8B 0.4943 1.1013 0.3705 0.078 Uiso calc R 1 . .
C C9 0.6573(4) 0.9186(3) 0.5014(3) 0.0485(9) Uani d . 1 . .
C C10 0.7614(4) 0.6221(3) 0.3812(3) 0.0472(9) Uani d . 1 . .
H H10 0.7746 0.7047 0.3502 0.057 Uiso calc R 1 . .
C C11 0.8495(4) 0.5228(3) 0.3433(3) 0.0524(9) Uani d . 1 . .
H H11 0.9219 0.5371 0.2865 0.063 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0988(8) 0.0647(6) 0.0845(7) 0.0221(6) -0.0005(7) -0.0039(6)
O1 0.085(2) 0.0749(19) 0.0659(19) 0.0180(17) 0.0322(15) 0.0188(15)
O2 0.0809(19) 0.0424(14) 0.0632(17) -0.0087(14) -0.0134(15) 0.0004(13)
O3 0.0644(18) 0.0686(18) 0.0576(16) -0.0019(14) -0.0194(15) -0.0017(15)
N1 0.0493(18) 0.0437(17) 0.0384(16) -0.0055(15) -0.0036(14) 0.0020(14)
C1 0.057(3) 0.050(2) 0.052(2) 0.003(2) -0.004(2) -0.0012(19)
C2 0.086(3) 0.045(2) 0.051(2) -0.004(2) 0.001(2) 0.0049(19)
C3 0.073(3) 0.052(2) 0.045(2) -0.013(2) 0.005(2) 0.006(2)
C4 0.050(2) 0.043(2) 0.044(2) -0.013(2) -0.0092(19) 0.0047(18)
C5 0.064(2) 0.049(2) 0.047(2) -0.010(2) 0.009(2) 0.0009(19)
C6 0.058(2) 0.073(2) 0.046(2) -0.006(2) -0.011(2) -0.0004(19)
C7 0.058(3) 0.070(3) 0.045(2) 0.009(3) -0.002(2) 0.008(2)
C8 0.079(3) 0.057(2) 0.060(2) 0.012(2) -0.004(2) 0.010(2)
C9 0.049(2) 0.049(2) 0.048(2) 0.003(2) 0.003(2) -0.002(2)
C10 0.050(2) 0.045(2) 0.046(2) -0.0057(19) -0.0001(18) 0.0037(17)
C11 0.052(2) 0.054(2) 0.051(2) -0.001(2) 0.001(2) 0.002(2)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C1 . 1.740(4) ?
O1 C7 . 1.417(4) ?
O1 H1 . 0.84 ?
O2 C9 . 1.341(4) ?
O2 C8 . 1.439(4) ?
O3 C9 . 1.227(4) ?
N1 C9 . 1.332(4) ?
N1 C5 . 1.453(3) ?
N1 C6 . 1.454(4) ?
C1 C11 . 1.369(4) ?
C1 C2 . 1.373(4) ?
C2 C3 . 1.376(4) ?
C2 H2 . 0.95 ?
C3 C4 . 1.392(4) ?
C3 H3 . 0.95 ?
C4 C10 . 1.375(4) ?
C4 C5 . 1.516(4) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.506(4) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.484(5) ?
C7 H7 . 1.0 ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C10 C11 . 1.389(4) ?
C10 H10 . 0.95 ?
C11 H11 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C7 O1 H1 . . 109.5 ?
C9 O2 C8 . . 121.5(3) ?
C9 N1 C5 . . 119.3(3) ?
C9 N1 C6 . . 124.0(3) ?
C5 N1 C6 . . 116.6(3) ?
C11 C1 C2 . . 121.1(4) ?
C11 C1 Cl1 . . 119.0(3) ?
C2 C1 Cl1 . . 119.9(3) ?
C1 C2 C3 . . 119.1(3) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C2 C3 C4 . . 121.4(4) ?
C2 C3 H3 . . 119.3 ?
C4 C3 H3 . . 119.3 ?
C10 C4 C3 . . 118.0(4) ?
C10 C4 C5 . . 124.0(3) ?
C3 C4 C5 . . 118.0(3) ?
N1 C5 C4 . . 114.0(3) ?
N1 C5 H5A . . 108.8 ?
C4 C5 H5A . . 108.8 ?
N1 C5 H5B . . 108.8 ?
C4 C5 H5B . . 108.8 ?
H5A C5 H5B . . 107.6 ?
N1 C6 C7 . . 110.0(3) ?
N1 C6 H6A . . 109.7 ?
C7 C6 H6A . . 109.7 ?
N1 C6 H6B . . 109.7 ?
C7 C6 H6B . . 109.7 ?
H6A C6 H6B . . 108.2 ?
O1 C7 C8 . . 112.7(3) ?
O1 C7 C6 . . 106.8(3) ?
C8 C7 C6 . . 109.1(3) ?
O1 C7 H7 . . 109.4 ?
C8 C7 H7 . . 109.4 ?
C6 C7 H7 . . 109.4 ?
O2 C8 C7 . . 111.9(3) ?
O2 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
O2 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
O3 C9 N1 . . 123.3(3) ?
O3 C9 O2 . . 117.2(4) ?
N1 C9 O2 . . 119.5(3) ?
C4 C10 C11 . . 121.3(3) ?
C4 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C1 C11 C10 . . 119.1(3) ?
C1 C11 H11 . . 120.4 ?
C10 C11 H11 . . 120.4 ?

