# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_4CC-o
_database_code_depnum_ccdc_archive 'CCDC 2001051'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        N-(4?-chlorosalicylidene)-4-chloroaniline
_chemical_name_common            
N-(2-Hydroxy-4-chlorobenzylidene)-4-chloroaniline
_chemical_melting_point          427
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   10.004(6)
_cell_length_b                   4.688(3)
_cell_length_c                   11.919(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.2393(10)
_cell_angle_gamma                90
_cell_volume                     558.1(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1817
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.560
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.862
_exptl_absorpt_correction_T_max  0.975
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            6122
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.039
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1275
_reflns_number_gt                1133
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_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)+1.5632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1275
_refine_ls_number_parameters     81
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_ref         0.1208
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.265
_refine_ls_restrained_S_all      1.265
_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
O1 O 0.4590(5) 0.2602(10) 0.3052(4) 0.0196(10) Uani 0.5 1 d . . P A -1
H1 H 0.496645 0.119548 0.337138 0.029 Uiso 0.5 1 calc R U P A -1
C1 C 0.3694(3) 0.3652(6) 0.3698(3) 0.0137(6) Uani 1 1 d . . . . .
H2 H 0.434210 0.289047 0.322906 0.016 Uiso 0.5 1 calc R U P A 2
C2 C 0.2784(3) 0.5684(7) 0.3273(3) 0.0146(6) Uani 1 1 d . . . . .
H3 H 0.281221 0.632022 0.251760 0.018 Uiso 1 1 calc R U . . .
C3 C 0.1840(3) 0.6765(7) 0.3963(3) 0.0141(6) Uani 1 1 d . . . . .
C4 C 0.1781(3) 0.5903(7) 0.5077(3) 0.0180(7) Uani 1 1 d . . . . .
H4 H 0.113159 0.668040 0.554225 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2695(3) 0.3877(7) 0.5491(3) 0.0178(7) Uani 1 1 d . . . . .
H5 H 0.266618 0.326302 0.624918 0.021 Uiso 1 1 calc R U . . .
C6 C 0.3659(3) 0.2722(6) 0.4814(3) 0.0126(6) Uani 1 1 d . . . . .
Cl1 Cl 0.07060(7) 0.92695(16) 0.34058(7) 0.0184(2) Uani 1 1 d . . . . .
C7 C 0.4601(17) 0.053(4) 0.5257(14) 0.0132(8) Uiso 0.5 1 d . . P B -1
H6 H 0.456776 -0.000669 0.602399 0.016 Uiso 0.5 1 calc R U P B -1
N1 N 0.5452(15) -0.068(3) 0.4671(11) 0.0132(8) Uiso 0.5 1 d . . P B -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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.022(2) 0.025(3) 0.013(2) 0.0024(19) 0.0041(17) 0.014(2)
C1 0.0135(13) 0.0123(15) 0.0155(15) 0.0011(12) 0.0021(11) 0.0010(11)
C2 0.0167(14) 0.0152(15) 0.0119(14) 0.0002(12) -0.0004(11) 0.0012(12)
C3 0.0122(13) 0.0104(14) 0.0192(16) -0.0012(12) -0.0042(12) 0.0006(11)
C4 0.0152(14) 0.0209(17) 0.0181(16) -0.0040(13) 0.0035(12) 0.0022(13)
C5 0.0176(15) 0.0213(18) 0.0144(15) 0.0028(13) 0.0002(12) -0.0017(13)
C6 0.0126(13) 0.0106(14) 0.0143(15) 0.0025(11) -0.0014(11) -0.0021(11)
Cl1 0.0163(4) 0.0155(4) 0.0229(4) -0.0035(3) -0.0053(3) 0.0062(3)

_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 1.310(5) . ?
O1 H1 0.8400 . ?
C1 C2 1.393(4) . ?
C1 C6 1.402(4) . ?
C1 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C2 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C3 Cl1 1.738(3) . ?
C4 C5 1.390(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.472(17) . ?
C7 N1 1.266(6) . ?
C7 H6 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
C1 O1 H1 109.5 . . ?
O1 C1 C2 119.8(3) . . ?
O1 C1 C6 119.7(3) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H2 119.7 . . ?
C6 C1 H2 119.7 . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H3 120.4 . . ?
C1 C2 H3 120.4 . . ?
C2 C3 C4 121.9(3) . . ?
C2 C3 Cl1 118.2(2) . . ?
C4 C3 Cl1 119.9(2) . . ?
C5 C4 C3 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 118.8(3) . . ?
C5 C6 C7 120.7(7) . . ?
C1 C6 C7 120.5(7) . . ?
N1 C7 C6 123.5(8) . . ?
N1 C7 H6 118.2 . . ?
C6 C7 H6 118.2 . . ?

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
O1 C1 C2 C3 179.7(4) . . . . ?
C6 C1 C2 C3 -0.4(5) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 Cl1 -179.3(2) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
Cl1 C3 C4 C5 179.4(2) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C1 0.2(5) . . . . ?
C4 C5 C6 C7 -178.5(8) . . . . ?
O1 C1 C6 C5 179.8(4) . . . . ?
C2 C1 C6 C5 -0.1(4) . . . . ?
O1 C1 C6 C7 -1.4(9) . . . . ?
C2 C1 C6 C7 178.6(8) . . . . ?
C5 C6 C7 N1 176.7(4) . . . . ?
C1 C6 C7 N1 -2.0(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1^a H1^a N1^a 0.84 1.82 2.579(15) 148.8 . yes

_refine_diff_density_max         0.406
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.085

_shelx_res_file                  
;
TITL N4CC_orange
    shelxl.res
    created by SHELXL-2018/1 at 13:20:20 on 04-Mar-2019
CELL 0.71075 10.0040 4.6880 11.9190 90.0000 93.2393 90.0000
ZERR 2.0 0.0060 0.0030 0.0070 0.0000 0.0010 0.0000
LATT 1
SYMM -X, 1/2+Y, 1/2-Z
REM  SPGR P21/c monoclinic
SFAC C H Cl N O
UNIT 26.000000 18.000000 4.000000 2.000000 2.000000
SIZE 0.19 0.18 0.08
TEMP -180.0
L.S. 30
FMAP 2
PLAN -20
ACTA
CONF
BOND$H

EADP C7 N1
HTAB O1 N1
LIST 4
WGHT    0.000000    1.563200
FVAR       2.76408
PART -1
O1    5    0.458951    0.260238    0.305234    10.50000    0.02161    0.02483 =
         0.01279    0.00237    0.00413    0.01413
AFIX 147
H1    2    0.496645    0.119548    0.337138    10.50000   -1.50000
PART 0
AFIX   0
C1    1    0.369355    0.365209    0.369848    11.00000    0.01348    0.01230 =
         0.01548    0.00112    0.00206    0.00100
PART 2
AFIX  43
H2    2    0.434210    0.289047    0.322906    10.50000   -1.20000
PART 0
AFIX   0
C2    1    0.278429    0.568418    0.327268    11.00000    0.01666    0.01522 =
         0.01185    0.00019   -0.00040    0.00119
AFIX  43
H3    2    0.281221    0.632022    0.251760    11.00000   -1.20000
AFIX   0
C3    1    0.184003    0.676459    0.396317    11.00000    0.01216    0.01039 =
         0.01924   -0.00125   -0.00419    0.00056
C4    1    0.178069    0.590319    0.507708    11.00000    0.01525    0.02094 =
         0.01807   -0.00399    0.00349    0.00221
AFIX  43
H4    2    0.113159    0.668040    0.554225    11.00000   -1.20000
AFIX   0
C5    1    0.269535    0.387696    0.549137    11.00000    0.01756    0.02131 =
         0.01444    0.00276    0.00017   -0.00166
AFIX  43
H5    2    0.266618    0.326302    0.624918    11.00000   -1.20000
AFIX   0
C6    1    0.365904    0.272211    0.481437    11.00000    0.01261    0.01056 =
         0.01433    0.00250   -0.00138   -0.00207
CL1   3    0.070602    0.926953    0.340580    11.00000    0.01626    0.01547 =
         0.02286   -0.00349   -0.00535    0.00617
PART -1
C7    1    0.460055    0.052806    0.525724    10.50000    0.01315
AFIX  43
H6    2    0.456776   -0.000669    0.602399    10.50000   -1.20000
AFIX   0
N1    4    0.545162   -0.068448    0.467116    10.50000    0.01315
PART 0

HKLF 4




REM  N4CC_orange
REM R1 =  0.0504 for    1133 Fo > 4sig(Fo)  and  0.0576 for all    1275 data
REM     81 parameters refined using      0 restraints

END

WGHT      0.0000      1.5632

REM Highest difference peak  0.406,  deepest hole -0.406,  1-sigma level  0.085
Q1    1   0.3751  0.3457  0.4331  11.00000  0.05    0.41
Q2    1   0.2125  0.5802  0.3595  11.00000  0.05    0.37
Q3    1   0.3044  0.4365  0.3429  11.00000  0.05    0.36
Q4    1   0.1278  0.2467  0.6476  11.00000  0.05    0.31
Q5    1   0.2069  0.9802  0.2210  11.00000  0.05    0.28
Q6    1   0.3326  0.3368  0.5149  11.00000  0.05    0.27
Q7    1   0.4033  0.1658  0.4930  11.00000  0.05    0.27
Q8    1   0.1279  0.6971  0.3754  11.00000  0.05    0.27
Q9    1   0.5566  0.1968  0.5839  11.00000  0.05    0.26
Q10   1   0.2040  0.4259  0.5183  11.00000  0.05    0.26
Q11   1   0.1648  0.7582  0.2354  11.00000  0.05    0.25
Q12   1   0.5985  0.2066  0.4029  11.00000  0.05    0.25
Q13   1   0.2470  0.5632  0.5240  11.00000  0.05    0.24
Q14   1   0.0925  0.5620  0.3039  11.00000  0.05    0.24
Q15   1   0.2704  0.6964  0.3788  11.00000  0.05    0.23
Q16   1   0.2835  0.6143  0.2982  11.00000  0.05    0.23
Q17   1   0.3894 -0.2629  0.4943  11.00000  0.05    0.22
Q18   1   0.5719  0.2541  0.1980  11.00000  0.05    0.22
Q19   1   0.1923  0.6788  0.4480  11.00000  0.05    0.22
Q20   1   0.1045  0.7703  0.5970  11.00000  0.05    0.22
;
_shelx_res_checksum              79099

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_4CC-y
_database_code_depnum_ccdc_archive 'CCDC 2001052'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        N-(4?-chlorosalicylidene)-4-chloroaniline
_chemical_name_common            
N-(2-Hydroxy-4-chlorobenzylidene)-4-chloroaniline
_chemical_melting_point          '417 (or phase transiiton to orange form)'
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11

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'
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           15
_space_group_name_H-M_alt        I2/c
_space_group_name_Hall           '-I 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+1/2'
'-x+1/2, y+1/2, -z+1'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   6.140(5)
_cell_length_b                   6.848(6)
_cell_length_c                   27.39(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.26(2)
_cell_angle_gamma                90
_cell_volume                     1146.8(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1729
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.545
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.718
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            6509
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.987
_diffrn_reflns_theta_max         27.450
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1298
_reflns_number_gt                1176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_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)+(0.0272P)²+2.8523P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1298
_refine_ls_number_parameters     81
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0967
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_restrained_S_all      1.113
_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
Cl1 Cl 0.30936(10) -0.05592(9) 0.03841(2) 0.02466(19) Uani 1 1 d . . . . .
C1 C 0.2019(4) -0.0232(3) 0.09436(7) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.3292(3) -0.0777(3) 0.13652(8) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.470391 -0.132277 0.134587 0.018 Uiso 1 1 calc R U . . .
C3 C 0.2474(3) -0.0514(3) 0.18155(8) 0.0156(4) Uani 1 1 d . . . . .
H2 H 0.333741 -0.086337 0.210814 0.023 Uiso 0.5 1 calc R U P A 2
O1 O 0.3856(5) -0.0804(4) 0.22299(11) 0.0169(6) Uani 0.5 1 d . . P B -1
H3 H 0.318053 -0.060319 0.247825 0.025 Uiso 0.5 1 calc R U P B -1
C4 C 0.0369(3) 0.0268(3) 0.18406(7) 0.0136(4) Uani 1 1 d . . . . .
C5 C -0.0875(3) 0.0788(3) 0.14070(8) 0.0136(4) Uani 1 1 d . . . . .
H4 H -0.230028 0.131071 0.142192 0.016 Uiso 1 1 calc R U . . .
C6 C -0.0060(4) 0.0551(3) 0.09570(8) 0.0163(4) Uani 1 1 d . . . . .
H5 H -0.090376 0.091614 0.066313 0.020 Uiso 1 1 calc R U . . .
C7 C -0.0504(14) 0.0534(12) 0.2310(3) 0.015(2) Uiso 0.5 1 d . . P C -1
H6 H -0.199129 0.090880 0.231605 0.018 Uiso 0.5 1 calc R U P C -1
N1 N 0.0656(11) 0.0282(9) 0.2716(2) 0.0121(18) Uiso 0.5 1 d . . P C -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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0280(3) 0.0337(3) 0.0134(3) -0.0023(2) 0.0080(2) -0.0008(3)
C1 0.0208(11) 0.0119(9) 0.0117(9) -0.0010(8) 0.0056(8) -0.0044(8)
C2 0.0147(10) 0.0112(9) 0.0182(10) -0.0021(8) 0.0022(8) 0.0001(8)
C3 0.0159(10) 0.0173(10) 0.0135(10) 0.0015(8) 0.0008(8) 0.0023(8)
O1 0.0144(15) 0.0234(16) 0.0126(14) 0.0021(12) -0.0001(11) 0.0049(12)
C4 0.0149(10) 0.0131(10) 0.0130(10) -0.0013(8) 0.0023(8) -0.0002(8)
C5 0.0140(10) 0.0104(9) 0.0159(10) 0.0012(8) -0.0006(8) -0.0006(8)
C6 0.0192(11) 0.0157(10) 0.0136(10) 0.0022(8) -0.0005(8) -0.0017(9)

_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 C1 1.738(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.388(3) . ?
C2 C3 1.385(3) . ?
C2 H1 0.9500 . ?
C3 O1 1.368(4) . ?
C3 C4 1.406(3) . ?
C3 H2 0.9500 . ?
O1 H3 0.8400 . ?
C4 C5 1.398(3) . ?
C4 C7 1.450(9) . ?
C5 C6 1.382(3) . ?
C5 H4 0.9500 . ?
C6 H5 0.9500 . ?
C7 N1 1.275(6) . ?
C7 H6 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 C6 122.1(2) . . ?
C2 C1 Cl1 118.01(17) . . ?
C6 C1 Cl1 119.84(17) . . ?
C1 C2 C3 119.0(2) . . ?
C1 C2 H1 120.5 . . ?
C3 C2 H1 120.5 . . ?
O1 C3 C2 118.2(2) . . ?
O1 C3 C4 121.2(2) . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H2 119.9 . . ?
C4 C3 H2 119.9 . . ?
C3 O1 H3 109.5 . . ?
C5 C4 C3 119.24(19) . . ?
C5 C4 C7 120.3(4) . . ?
C3 C4 C7 120.5(4) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H4 119.6 . . ?
C4 C5 H4 119.6 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 H5 120.7 . . ?
C1 C6 H5 120.7 . . ?
N1 C7 C4 122.2(5) . . ?
N1 C7 H6 118.9 . . ?
C4 C7 H6 118.9 . . ?

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
C6 C1 C2 C3 -0.7(3) . . . . ?
Cl1 C1 C2 C3 179.50(16) . . . . ?
C1 C2 C3 O1 -171.1(2) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
O1 C3 C4 C5 171.3(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
O1 C3 C4 C7 -8.6(5) . . . . ?
C2 C3 C4 C7 179.6(4) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C7 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C2 C1 C6 C5 -0.1(3) . . . . ?
Cl1 C1 C6 C5 179.75(16) . . . . ?
C5 C4 C7 N1 -172.2(7) . . . . ?
C3 C4 C7 N1 7.8(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1^a H3^a N1^a 0.84 1.84 2.582(7) 146.7 . yes

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.073

_shelx_res_file                  
;
TITL N4CC_yellow
    shelxl.res
    created by SHELXL-2018/1 at 18:33:52 on 05-Nov-2019
CELL 0.71075 6.1400 6.8480 27.3900 90.0000 95.2600 90.0000
ZERR 4.0 0.0050 0.0060 0.0200 0.0000 0.0200 0.0000
LATT 2
SYMM             - X ,              Y ,    0.50000 - Z
REM  SPGR I2/c monoclinic
SFAC C H Cl N O
UNIT 52.000000 36.000000 8.000000 4.000000 4.000000
SIZE 0.30 0.27 0.03
TEMP -180.0
L.S. 30
FMAP 2
PLAN -20
ACTA
CONF
BOND$H

HTAB O1 N1
LIST 4
WGHT    0.027200    2.852300
FVAR       1.08802
CL1   3    0.309364   -0.055918    0.038409    11.00000    0.02799    0.03374 =
         0.01338   -0.00231    0.00801   -0.00077
C1    1    0.201916   -0.023152    0.094361    11.00000    0.02081    0.01189 =
         0.01169   -0.00096    0.00560   -0.00444
C2    1    0.329195   -0.077697    0.136519    11.00000    0.01470    0.01125 =
         0.01818   -0.00206    0.00219    0.00013
AFIX  43
H1    2    0.470391   -0.132277    0.134587    11.00000   -1.20000
AFIX   0
C3    1    0.247415   -0.051430    0.181554    11.00000    0.01586    0.01732 =
         0.01352    0.00152    0.00084    0.00227
PART 2
AFIX  43
H2    2    0.333741   -0.086337    0.210814    10.50000   -1.50000
PART -1
AFIX   0
O1    5    0.385629   -0.080370    0.222987    10.50000    0.01443    0.02337 =
         0.01260    0.00208   -0.00005    0.00495
AFIX  83
H3    2    0.318053   -0.060319    0.247825    10.50000   -1.50000
PART 0
AFIX   0
C4    1    0.036941    0.026774    0.184065    11.00000    0.01486    0.01307 =
         0.01297   -0.00126    0.00229   -0.00022
C5    1   -0.087489    0.078766    0.140697    11.00000    0.01405    0.01041 =
         0.01590    0.00118   -0.00060   -0.00060
AFIX  43
H4    2   -0.230028    0.131071    0.142192    11.00000   -1.20000
AFIX   0
C6    1   -0.005967    0.055107    0.095700    11.00000    0.01921    0.01568 =
         0.01365    0.00224   -0.00050   -0.00173
AFIX  43
H5    2   -0.090376    0.091614    0.066313    11.00000   -1.20000
PART -1
AFIX   0
C7    1   -0.050419    0.053391    0.231032    10.50000    0.01534
AFIX  43
H6    2   -0.199129    0.090880    0.231605    10.50000   -1.20000
AFIX   0
N1    4    0.065566    0.028191    0.271600    10.50000    0.01207
PART 0

HKLF 4 1 0.0000 0.0000 1.0000 0.0000 1.0000 0.0000 -1.0000 0.0000 -1.0000




REM  N4CC_yellow
REM R1 =  0.0447 for    1176 Fo > 4sig(Fo)  and  0.0518 for all    1298 data
REM     81 parameters refined using      0 restraints

END

WGHT      0.0270      2.8560

REM Highest difference peak  0.352,  deepest hole -0.292,  1-sigma level  0.073
Q1    1  -0.0091  0.0794  0.1604  11.00000  0.05    0.35
Q2    1   0.2803 -0.0733  0.1588  11.00000  0.05    0.33
Q3    1   0.1371 -0.0355  0.1817  11.00000  0.05    0.30
Q4    1   0.0004  0.0306  0.2041  11.00000  0.05    0.26
Q5    1   0.2467 -0.0930 -0.0274  11.00000  0.05    0.25
Q6    1   0.0000 -0.0125  0.2500  10.50000  0.05    0.25
Q7    1   0.2085  0.0842 -0.0017  11.00000  0.05    0.24
Q8    1   0.2459 -0.0675  0.1161  11.00000  0.05    0.24
Q9    1  -0.0393  0.0540  0.1184  11.00000  0.05    0.22
Q10   1   0.1076  0.0411  0.0977  11.00000  0.05    0.21
Q11   1   0.4558 -0.3032  0.2299  11.00000  0.05    0.20
Q12   1   0.1699 -0.3224  0.1106  11.00000  0.05    0.20
Q13   1  -0.1657  0.0668  0.1401  11.00000  0.05    0.20
Q14   1   0.4949 -0.2213  0.0930  11.00000  0.05    0.20
Q15   1   0.2469  0.2210  0.0896  11.00000  0.05    0.20
Q16   1   0.2883 -0.0903  0.1984  11.00000  0.05    0.19
Q17   1   0.3508 -0.2905  0.0714  11.00000  0.05    0.18
Q18   1   0.1520 -0.0781  0.0257  11.00000  0.05    0.18
Q19   1   0.2754  0.2536  0.0403  11.00000  0.05    0.18
Q20   1  -0.0085 -0.1831  0.1828  11.00000  0.05    0.18
;
_shelx_res_checksum              49884

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
####################################################################### 
# 
# 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_5CC-o
_database_code_depnum_ccdc_archive 'CCDC 2001053'
loop_
_audit_author_name
_audit_author_address
'Isao Yoshikawa'
;Institute of Industrial Science, The University of Tokyo
Japan
;
_audit_update_record             
;
2020-05-05 deposited with the CCDC.	2020-07-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        N-(5?-chlorosalicylidene)-4-chloroaniline
_chemical_name_common            
N-(2-Hydroxy-5-chlorobenzylidene)-4-chloroaniline
_chemical_melting_point          422
_chemical_formula_moiety         'C13 H9 Cl2 N O'
_chemical_formula_sum            'C13 H9 Cl2 N O'
_chemical_formula_weight         266.11

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'
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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   20.427(6)
_cell_length_b                   4.5728(13)
_cell_length_c                   12.101(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.301(5)
_cell_angle_gamma                90
_cell_volume                     1129.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    3029
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.565
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.554
_shelx_estimated_absorpt_T_min   0.821
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.865
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'VariMax DW with Saturn'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            12645
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.996
_diffrn_reflns_theta_max         27.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2578
_reflns_number_gt                2244
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r3'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r3'
_computing_structure_solution    'SHELXS Version 2013/1 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'
_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)+(0.0372P)²+0.3395P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2578
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0830
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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
O1 O 0.26851(6) 0.7565(3) 0.34350(10) 0.0189(3) Uani 1 1 d . . . . .
H1 H 0.2479(11) 0.642(5) 0.376(2) 0.049(8) Uiso 1 1 d . . . . .
C1 C 0.31296(8) 0.8711(3) 0.41720(13) 0.0134(3) Uani 1 1 d . . . . .
C2 C 0.35790(8) 1.0741(4) 0.38092(13) 0.0168(3) Uani 1 1 d . . . . .
H2 H 0.356596 1.130576 0.305316 0.020 Uiso 1 1 calc R U . . .
C3 C 0.40445(8) 1.1951(4) 0.45319(14) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.435390 1.331805 0.427524 0.020 Uiso 1 1 calc R U . . .
C4 C 0.40541(7) 1.1140(3) 0.56423(13) 0.0130(3) Uani 1 1 d . . . . .
C5 C 0.36117(7) 0.9165(3) 0.60287(13) 0.0132(3) Uani 1 1 d . . . . .
H4 H 0.362285 0.866006 0.679076 0.016 Uiso 1 1 calc R U . . .
C6 C 0.31411(8) 0.7887(3) 0.52953(13) 0.0113(3) Uani 1 1 d . . . . .
Cl1 Cl 0.46382(2) 1.26797(9) 0.65593(3) 0.01812(12) Uani 1 1 d . . . . .
C7 C 0.26800(7) 0.5782(3) 0.57112(13) 0.0123(3) Uani 1 1 d . . . . .
H5 H 0.268828 0.536029 0.648032 0.015 Uiso 1 1 calc R U . . .
N1 N 0.22600(6) 0.4473(3) 0.50622(10) 0.0121(3) Uani 1 1 d . . . . .
C8 C 0.18149(7) 0.2395(3) 0.54799(13) 0.0116(3) Uani 1 1 d . . . . .
C9 C 0.18275(8) 0.1401(4) 0.65737(13) 0.0148(3) Uani 1 1 d . . . . .
H6 H 0.215003 0.212293 0.709158 0.018 Uiso 1 1 calc R U . . .
C10 C 0.13722(8) -0.0630(3) 0.69060(13) 0.0155(3) Uani 1 1 d . . . . .
H7 H 0.138342 -0.130816 0.764855 0.019 Uiso 1 1 calc R U . . .
C11 C 0.09014(7) -0.1665(3) 0.61521(14) 0.0134(3) Uani 1 1 d . . . . .
C12 C 0.08807(8) -0.0743(3) 0.50616(13) 0.0155(3) Uani 1 1 d . . . . .
H8 H 0.055780 -0.148057 0.454777 0.019 Uiso 1 1 calc R U . . .
C13 C 0.13414(8) 0.1281(3) 0.47331(13) 0.0139(3) Uani 1 1 d . . . . .
H9 H 0.133341 0.191674 0.398536 0.017 Uiso 1 1 calc R U . . .
Cl2 Cl 0.03293(2) -0.41667(8) 0.66025(3) 0.01801(12) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0222(6) 0.0235(7) 0.0107(6) 0.0013(5) -0.0019(5) -0.0095(5)
C1 0.0141(7) 0.0144(8) 0.0117(7) -0.0010(6) 0.0014(6) 0.0013(6)
C2 0.0205(8) 0.0186(8) 0.0114(7) 0.0019(6) 0.0032(6) -0.0020(7)
C3 0.0155(8) 0.0163(8) 0.0179(8) 0.0001(7) 0.0052(6) -0.0021(7)
C4 0.0109(7) 0.0134(8) 0.0146(8) -0.0020(6) 0.0000(6) 0.0000(6)
C5 0.0144(8) 0.0137(8) 0.0114(7) 0.0002(6) 0.0012(6) 0.0021(6)
C6 0.0121(7) 0.0108(7) 0.0112(7) -0.0003(6) 0.0024(6) 0.0014(6)
Cl1 0.0144(2) 0.0214(2) 0.0184(2) -0.00157(16) -0.00188(15) -0.00500(16)
C7 0.0153(8) 0.0112(7) 0.0105(7) 0.0010(6) 0.0022(6) 0.0012(6)
N1 0.0131(6) 0.0100(6) 0.0133(6) -0.0003(5) 0.0023(5) 0.0001(5)
C8 0.0111(7) 0.0095(7) 0.0146(8) 0.0001(6) 0.0025(6) 0.0007(6)
C9 0.0138(8) 0.0164(8) 0.0139(8) -0.0006(6) -0.0015(6) -0.0008(6)
C10 0.0179(8) 0.0143(8) 0.0144(8) 0.0021(6) 0.0021(6) -0.0005(6)
C11 0.0109(7) 0.0091(7) 0.0206(8) -0.0014(6) 0.0047(6) -0.0003(6)
C12 0.0145(8) 0.0146(8) 0.0171(8) -0.0028(6) -0.0017(6) -0.0012(6)
C13 0.0168(8) 0.0127(7) 0.0122(7) -0.0004(6) 0.0001(6) 0.0007(6)
Cl2 0.0163(2) 0.0142(2) 0.0239(2) -0.00116(16) 0.00647(15) -0.00448(16)

_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 1.3524(19) . ?
O1 H1 0.79(2) . ?
C1 C2 1.389(2) . ?
C1 C6 1.410(2) . ?
C2 C3 1.381(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.373(2) . ?
C4 Cl1 1.7447(16) . ?
C5 C6 1.409(2) . ?
C5 H4 0.9500 . ?
C6 C7 1.451(2) . ?
C7 N1 1.287(2) . ?
C7 H5 0.9500 . ?
N1 C8 1.422(2) . ?
C8 C13 1.394(2) . ?
C8 C9 1.399(2) . ?
C9 C10 1.385(2) . ?
C9 H6 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H7 0.9500 . ?
C11 C12 1.384(2) . ?
C11 Cl2 1.7387(16) . ?
C12 C13 1.389(2) . ?
C12 H8 0.9500 . ?
C13 H9 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
C1 O1 H1 106.5(18) . . ?
O1 C1 C2 119.02(14) . . ?
O1 C1 C6 121.14(14) . . ?
C2 C1 C6 119.85(14) . . ?
C3 C2 C1 120.96(15) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 119.12(15) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 121.30(14) . . ?
C5 C4 Cl1 119.44(12) . . ?
C3 C4 Cl1 119.26(12) . . ?
C4 C5 C6 120.01(14) . . ?
C4 C5 H4 120.0 . . ?
C6 C5 H4 120.0 . . ?
C5 C6 C1 118.75(14) . . ?
C5 C6 C7 119.52(14) . . ?
C1 C6 C7 121.73(14) . . ?
N1 C7 C6 121.53(14) . . ?
N1 C7 H5 119.2 . . ?
C6 C7 H5 119.2 . . ?
C7 N1 C8 120.92(13) . . ?
C13 C8 C9 118.73(14) . . ?
C13 C8 N1 116.81(14) . . ?
C9 C8 N1 124.46(14) . . ?
C10 C9 C8 120.36(15) . . ?
C10 C9 H6 119.8 . . ?
C8 C9 H6 119.8 . . ?
C11 C10 C9 119.69(15) . . ?
C11 C10 H7 120.2 . . ?
C9 C10 H7 120.2 . . ?
C10 C11 C12 121.26(15) . . ?
C10 C11 Cl2 118.48(13) . . ?
C12 C11 Cl2 120.26(12) . . ?
C11 C12 C13 118.71(14) . . ?
C11 C12 H8 120.6 . . ?
C13 C12 H8 120.6 . . ?
C12 C13 C8 121.24(15) . . ?
C12 C13 H9 119.4 . . ?
C8 C13 H9 119.4 . . ?

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
O1 C1 C2 C3 -179.53(14) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 -0.9(2) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 Cl1 -179.62(12) . . . . ?
C3 C4 C5 C6 0.8(2) . . . . ?
Cl1 C4 C5 C6 -179.46(11) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C4 C5 C6 C7 179.43(14) . . . . ?
O1 C1 C6 C5 -179.54(14) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
O1 C1 C6 C7 0.1(2) . . . . ?
C2 C1 C6 C7 179.80(15) . . . . ?
C5 C6 C7 N1 -177.10(14) . . . . ?
C1 C6 C7 N1 3.3(2) . . . . ?
C6 C7 N1 C8 179.42(13) . . . . ?
C7 N1 C8 C13 174.59(14) . . . . ?
C7 N1 C8 C9 -6.0(2) . . . . ?
C13 C8 C9 C10 -0.7(2) . . . . ?
N1 C8 C9 C10 179.94(14) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C9 C10 C11 C12 1.0(2) . . . . ?
C9 C10 C11 Cl2 -178.96(12) . . . . ?
C10 C11 C12 C13 -0.6(2) . . . . ?
Cl2 C11 C12 C13 179.34(12) . . . . ?
C11 C12 C13 C8 -0.5(2) . . . . ?
C9 C8 C13 C12 1.1(2) . . . . ?
N1 C8 C13 C12 -179.50(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7 H5 O1 0.95 2.55 3.381(2) 146.4 4_576 yes
O1 H1 N1 0.79(2) 1.88(3) 2.6016(19) 152(2) . yes

_refine_diff_density_max         0.293
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.067

_shelx_res_file                  
;
TITL 5CC
    shelxl.res
    created by SHELXL-2018/1 at 11:46:23 on 20-Jun-2018
CELL 0.71075 20.4270 4.5728 12.1010 90.0000 92.3010 90.0000
ZERR 4.0 0.0060 0.0013 0.0040 0.0000 0.0050 0.0000
LATT 1
SYMM    -X, .50+Y, .50-Z
REM  SPGR P21/c monoclinic
SFAC C H Cl N O
UNIT 52.000000 36.000000 8.000000 4.000000 4.000000
SIZE 0.37 0.07 0.04
TEMP -180.0
L.S. 30
FMAP 2
PLAN -20
ACTA
CONF
BOND$H

EQIV $1 x, -y+3/2, z+1/2
HTAB C7 O1_$1
HTAB O1 N1
LIST 4
WGHT    0.037200    0.339500
FVAR       1.67043
O1    5    0.268514    0.756540    0.343499    11.00000    0.02221    0.02355 =
         0.01073    0.00128   -0.00186   -0.00945
H1    2    0.247943    0.642236    0.376193    11.00000    0.04889
C1    1    0.312957    0.871076    0.417201    11.00000    0.01409    0.01442 =
         0.01167   -0.00104    0.00136    0.00127
C2    1    0.357896    1.074111    0.380923    11.00000    0.02049    0.01857 =
         0.01139    0.00190    0.00324   -0.00197
AFIX  43
H2    2    0.356596    1.130576    0.305316    11.00000   -1.20000
AFIX   0
C3    1    0.404448    1.195105    0.453193    11.00000    0.01552    0.01633 =
         0.01791    0.00014    0.00518   -0.00208
AFIX  43
H3    2    0.435390    1.331805    0.427524    11.00000   -1.20000
AFIX   0
C4    1    0.405414    1.113983    0.564230    11.00000    0.01089    0.01341 =
         0.01458   -0.00196    0.00000   -0.00004
C5    1    0.361167    0.916479    0.602870    11.00000    0.01439    0.01373 =
         0.01140    0.00025    0.00121    0.00206
AFIX  43
H4    2    0.362285    0.866006    0.679076    11.00000   -1.20000
AFIX   0
C6    1    0.314109    0.788661    0.529532    11.00000    0.01209    0.01077 =
         0.01121   -0.00032    0.00238    0.00143
CL1   3    0.463817    1.267970    0.655925    11.00000    0.01439    0.02142 =
         0.01835   -0.00157   -0.00188   -0.00500
C7    1    0.268004    0.578223    0.571119    11.00000    0.01527    0.01118 =
         0.01051    0.00096    0.00220    0.00115
AFIX  43
H5    2    0.268828    0.536029    0.648032    11.00000   -1.20000
AFIX   0
N1    4    0.225998    0.447326    0.506223    11.00000    0.01310    0.00998 =
         0.01334   -0.00030    0.00231    0.00011
C8    1    0.181488    0.239549    0.547995    11.00000    0.01106    0.00947 =
         0.01455    0.00006    0.00249    0.00072
C9    1    0.182749    0.140141    0.657372    11.00000    0.01380    0.01642 =
         0.01388   -0.00064   -0.00153   -0.00080
AFIX  43
H6    2    0.215003    0.212293    0.709158    11.00000   -1.20000
AFIX   0
C10   1    0.137216   -0.062980    0.690600    11.00000    0.01788    0.01428 =
         0.01436    0.00214    0.00214   -0.00046
AFIX  43
H7    2    0.138342   -0.130816    0.764855    11.00000   -1.20000
AFIX   0
C11   1    0.090144   -0.166453    0.615205    11.00000    0.01088    0.00911 =
         0.02064   -0.00136    0.00468   -0.00025
C12   1    0.088073   -0.074318    0.506158    11.00000    0.01454    0.01465 =
         0.01707   -0.00277   -0.00167   -0.00116
AFIX  43
H8    2    0.055780   -0.148057    0.454777    11.00000   -1.20000
AFIX   0
C13   1    0.134136    0.128070    0.473314    11.00000    0.01685    0.01270 =
         0.01218   -0.00042    0.00008    0.00065
AFIX  43
H9    2    0.133341    0.191674    0.398536    11.00000   -1.20000
AFIX   0
CL2   3    0.032934   -0.416671    0.660254    11.00000    0.01634    0.01421 =
         0.02394   -0.00116    0.00647   -0.00448

HKLF 4




REM  5CC
REM R1 =  0.0333 for    2244 Fo > 4sig(Fo)  and  0.0395 for all    2578 data
REM    158 parameters refined using      0 restraints

END

WGHT      0.0372      0.3395

REM Highest difference peak  0.293,  deepest hole -0.279,  1-sigma level  0.067
Q1    1   0.3986  1.1830  0.5164  11.00000  0.05    0.29
Q2    1   0.3874  1.0835  0.4167  11.00000  0.05    0.29
Q3    1   0.2884  0.6889  0.5475  11.00000  0.05    0.27
Q4    1   0.1799  0.2042  0.6005  11.00000  0.05    0.25
Q5    1   0.3573  1.2532  0.6173  11.00000  0.05    0.24
Q6    1   0.3369  0.9881  0.4006  11.00000  0.05    0.24
Q7    1   0.0926 -0.1304  0.5607  11.00000  0.05    0.23
Q8    1   0.3783  1.0632  0.5794  11.00000  0.05    0.23
Q9    1   0.3167  0.7970  0.4765  11.00000  0.05    0.23
Q10   1   0.3990  0.9855  0.5828  11.00000  0.05    0.23
Q11   1   0.2335  0.4582  0.4462  11.00000  0.05    0.22
Q12   1   0.1191 -0.0412  0.4875  11.00000  0.05    0.22
Q13   1   0.0500  0.1021  0.7064  11.00000  0.05    0.22
Q14   1   0.3326  0.8887  0.5666  11.00000  0.05    0.22
Q15   1   0.0380  0.1126  0.5539  11.00000  0.05    0.22
Q16   1   0.4462  1.4604  0.8020  11.00000  0.05    0.21
Q17   1   0.1042  0.0909  0.8404  11.00000  0.05    0.21
Q18   1   0.1220 -0.1477  0.6442  11.00000  0.05    0.20
Q19   1   0.3539  1.1223  0.3605  11.00000  0.05    0.19
Q20   1  -0.0008 -0.2399  0.5154  11.00000  0.05    0.19
;
_shelx_res_checksum              12577

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichroromethane, hexane'
