# 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_20180425-1
_database_code_depnum_ccdc_archive 'CCDC 1992175'
loop_
_audit_author_name
_audit_author_address
'Liu Hui'
;Jiaxing University
China
;
_audit_update_record             
;
2020-10-29 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2020-03-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H10 Cl N O'
_chemical_formula_sum            'C15 H10 Cl N O'
_chemical_formula_weight         255.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.2298(4)
_cell_length_b                   20.4052(11)
_cell_length_c                   11.8040(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.895(8)
_cell_angle_gamma                90
_cell_volume                     1227.90(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.7710
_cell_measurement_theta_min      4.4490
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0152
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.899
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3130
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0802
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.899
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00   4.00   1.00    5.00    --  -15.89  57.00 150.00   30
  2  ω    -49.00  60.00   1.00    5.00    --   16.05   0.00-120.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0770184000
_diffrn_orient_matrix_UB_12      0.0006835000
_diffrn_orient_matrix_UB_13      0.0576504000
_diffrn_orient_matrix_UB_21      -0.0125644000
_diffrn_orient_matrix_UB_22      0.0345900000
_diffrn_orient_matrix_UB_23      0.0009956000
_diffrn_orient_matrix_UB_31      -0.1150000000
_diffrn_orient_matrix_UB_32      -0.0032799000
_diffrn_orient_matrix_UB_33      0.0219670000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1577
_reflns_number_total             1943
_reflns_odcompleteness_completeness 87.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1943
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0358P)²+0.4896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C11(H11), C7(H7), C15(H15), C5(H5), C6(H6), C12(H12),
 C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.98623(11) 0.31066(3) 0.59065(5) 0.0564(2) Uani 1 1 d . . . . .
O1 O 0.7192(3) 0.53797(7) 0.40057(15) 0.0532(4) Uani 1 1 d . . . . .
N1 N 0.7680(3) 0.42960(8) 0.45536(15) 0.0406(4) Uani 1 1 d . . . . .
H1 H 0.9102 0.4334 0.5081 0.049 Uiso 1 1 calc R . . . .
C2 C 0.6395(4) 0.36969(9) 0.42469(18) 0.0362(5) Uani 1 1 d . . . . .
C8 C 0.4057(4) 0.45330(10) 0.31603(19) 0.0399(5) Uani 1 1 d . . . . .
C1 C 0.6443(4) 0.48090(9) 0.39305(19) 0.0401(5) Uani 1 1 d . . . . .
C10 C 0.6040(4) 0.24726(9) 0.43362(19) 0.0368(5) Uani 1 1 d . . . . .
C3 C 0.4041(4) 0.38575(9) 0.33403(19) 0.0378(5) Uani 1 1 d . . . . .
C9 C 0.7177(4) 0.31194(9) 0.47289(18) 0.0379(5) Uani 1 1 d . . . . .
C4 C 0.1970(4) 0.34824(11) 0.27375(19) 0.0446(5) Uani 1 1 d . . . . .
H4 H 0.1920 0.3032 0.2855 0.054 Uiso 1 1 calc R . . . .
C11 C 0.6411(4) 0.22090(10) 0.3304(2) 0.0468(6) Uani 1 1 d . . . . .
H11 H 0.7402 0.2438 0.2872 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2064(4) 0.48455(11) 0.2384(2) 0.0507(6) Uani 1 1 d . . . . .
H7 H 0.2098 0.5296 0.2271 0.061 Uiso 1 1 calc R . . . .
C15 C 0.4594(4) 0.21181(11) 0.4971(2) 0.0512(6) Uani 1 1 d . . . . .
H15 H 0.4350 0.2281 0.5676 0.061 Uiso 1 1 calc R . . . .
C5 C -0.0018(4) 0.37953(11) 0.1958(2) 0.0518(6) Uani 1 1 d . . . . .
H5 H -0.1414 0.3549 0.1543 0.062 Uiso 1 1 calc R . . . .
C6 C 0.0014(4) 0.44659(11) 0.1778(2) 0.0539(6) Uani 1 1 d . . . . .
H6 H -0.1351 0.4663 0.1247 0.065 Uiso 1 1 calc R . . . .
C12 C 0.5331(5) 0.16109(11) 0.2903(2) 0.0512(6) Uani 1 1 d . . . . .
H12 H 0.5603 0.1439 0.2209 0.061 Uiso 1 1 calc R . . . .
C13 C 0.3868(5) 0.12743(11) 0.3528(2) 0.0584(7) Uani 1 1 d . . . . .
H13 H 0.3111 0.0876 0.3254 0.070 Uiso 1 1 calc R . . . .
C14 C 0.3511(5) 0.15232(12) 0.4562(2) 0.0630(7) Uani 1 1 d . . . . .
H14 H 0.2530 0.1289 0.4991 0.076 Uiso 1 1 calc R . . . .


_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 C9 1.742(2) . ?
O1 C1 1.226(2) . ?
N1 H1 0.8600 . ?
N1 C2 1.403(2) . ?
N1 C1 1.357(3) . ?
C2 C3 1.476(3) . ?
C2 C9 1.332(3) . ?
C8 C1 1.481(3) . ?
C8 C3 1.395(3) . ?
C8 C7 1.381(3) . ?
C10 C9 1.479(3) . ?
C10 C11 1.385(3) . ?
C10 C15 1.382(3) . ?
C3 C4 1.386(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.385(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.380(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.361(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 0.9300 . ?

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 N1 H1 123.6 . . ?
C1 N1 H1 123.6 . . ?
C1 N1 C2 112.90(16) . . ?
N1 C2 C3 105.51(16) . . ?
C9 C2 N1 125.21(18) . . ?
C9 C2 C3 129.24(18) . . ?
C3 C8 C1 108.35(18) . . ?
C7 C8 C1 129.76(19) . . ?
C7 C8 C3 121.9(2) . . ?
O1 C1 N1 126.0(2) . . ?
O1 C1 C8 128.1(2) . . ?
N1 C1 C8 105.89(16) . . ?
C11 C10 C9 119.81(19) . . ?
C15 C10 C9 121.83(19) . . ?
C15 C10 C11 118.4(2) . . ?
C8 C3 C2 107.31(17) . . ?
C4 C3 C2 132.77(19) . . ?
C4 C3 C8 119.86(19) . . ?
C2 C9 Cl1 118.03(15) . . ?
C2 C9 C10 126.28(19) . . ?
C10 C9 Cl1 115.65(15) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 H4 120.9 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.4 . . ?
C8 C7 H7 121.1 . . ?
C8 C7 C6 117.8(2) . . ?
C6 C7 H7 121.1 . . ?
C10 C15 H15 119.9 . . ?
C14 C15 C10 120.1(2) . . ?
C14 C15 H15 119.9 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 120.5(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.6(2) . . ?
C13 C14 H14 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.065
_oxdiff_exptl_absorpt_empirical_full_min 0.892
