# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jcm004
_database_code_depnum_ccdc_archive 'CCDC 1893725'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 Cl O2'
_chemical_formula_sum            'C12 H13 Cl O2'
_chemical_formula_weight         224.67
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H13 Cl O2'
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'
Cl Cl 0.3639 0.7018 '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'

_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      orthorhombic
_space_group_IT_number           19
_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, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.1261(4)
_cell_length_b                   8.1012(6)
_cell_length_c                   18.5115(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1068.67(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2661
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      74.8130
_cell_measurement_theta_min      4.7460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.839
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -5 0 0.0624
0 5 0 0.0624
-1 0 -12 0.0283
1 0 12 0.0331
-2 4 5 0.0858
1 -4 -6 0.0502
4 2 -1 0.0459
5 1 -1 0.0435
-4 0 -6 0.1074
-4 0 3 0.1342
-4 -2 4 0.1331

_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.061
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0145 -4.9932 -0.0074 0.0895 0.4126 -0.8512
-0.0145 4.9932 0.0074 -0.0895 -0.4126 0.8512
-1.0022 0.0023 -12.0015 0.9915 0.1653 0.1843
1.0022 -0.0023 12.0015 -0.9915 -0.1653 -0.1843
-2.0140 3.9926 5.0085 -0.4915 0.0716 0.8321
1.0125 -3.9928 -6.0078 0.5716 0.1207 -0.7303
3.9996 1.9991 -1.0005 0.0582 -0.9463 -0.0291
5.0039 1.0009 -1.0028 0.0789 -1.0585 -0.2937
-4.0059 -0.0003 -5.9979 0.4860 0.7641 0.4221
-4.0053 -0.0023 3.0038 -0.2597 0.7861 0.3546
-3.9994 -1.9998 4.0011 -0.3068 0.9536 0.0066

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            4864
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.176
_diffrn_reflns_theta_min         4.778
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  32.00   1.00    1.00    --  -41.80  38.00  90.00   98
  2  ω    -70.00  31.00   1.00    1.00    --  -41.80  57.00 -30.00  101
  3  ω     81.00 178.00   1.00    2.00    --  109.13  30.00 120.00   97
  4  ω     36.00 117.00   1.00    2.00    --  109.13-125.00-120.00   81
  5  ω     56.00 178.00   1.00    2.00    --  109.13  15.00-120.00  122
  6  ω     36.00 117.00   1.00    2.00    --  109.13-125.00  60.00   81
  7  ω   -114.00 -21.00   1.00    1.00    --  -41.80 -57.00  90.00   93
  8  ω   -116.00 -17.00   1.00    1.00    --  -41.80 -38.00 -30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0027269000
_diffrn_orient_matrix_UB_12      -0.0177938000
_diffrn_orient_matrix_UB_13      -0.0828490000
_diffrn_orient_matrix_UB_21      -0.1943958000
_diffrn_orient_matrix_UB_22      -0.0832004000
_diffrn_orient_matrix_UB_23      0.0024445000
_diffrn_orient_matrix_UB_31      -0.0942280000
_diffrn_orient_matrix_UB_32      0.1702138000
_diffrn_orient_matrix_UB_33      -0.0074516000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.870
_reflns_number_gt                1804
_reflns_number_total             2045
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 640 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.057(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         2045
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.084
_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)+(0.0295P)²+0.4944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0753
_refine_ls_wR_factor_ref         0.0882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H4 of C4, H5 of C5, H3 of C3, H2A of C2
 At 1.5 times of:
  H2 of C12
2. Restrained distances
 O2-H2
 0.84 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.20330(11) 0.64780(11) 0.34891(4) 0.0217(2) Uani 1 1 d . . . . .
O1 O 0.1943(3) 0.3667(3) 0.47202(11) 0.0192(5) Uani 1 1 d . . . . .
O2 O 0.5135(3) 0.1620(3) 0.39497(12) 0.0174(5) Uani 1 1 d D . . . .
C1 C 0.5079(5) 0.4648(5) 0.39199(17) 0.0132(7) Uani 1 1 d . . . . .
C2 C 0.6914(5) 0.4601(4) 0.41911(16) 0.0169(7) Uani 1 1 d . . . . .
H2A H 0.751894 0.356189 0.423975 0.020 Uiso 1 1 calc R . . . .
C3 C 0.7875(5) 0.6012(4) 0.43904(16) 0.0192(7) Uani 1 1 d . . . . .
H3 H 0.910362 0.592926 0.458589 0.023 Uiso 1 1 calc R . . . .
C4 C 0.7042(6) 0.7552(5) 0.43047(18) 0.0209(7) Uani 1 1 d . . . . .
H4 H 0.769446 0.852599 0.444166 0.025 Uiso 1 1 calc R . . . .
C5 C 0.5249(5) 0.7651(5) 0.40170(19) 0.0198(8) Uani 1 1 d . . . . .
H5 H 0.467585 0.869622 0.394361 0.024 Uiso 1 1 calc R . . . .
C6 C 0.4303(4) 0.6222(5) 0.38378(17) 0.0170(8) Uani 1 1 d . . . . .
C7 C 0.4060(5) 0.3043(4) 0.37413(17) 0.0137(7) Uani 1 1 d . . . . .
C8 C 0.3744(5) 0.2842(5) 0.29218(17) 0.0183(8) Uani 1 1 d . . . . .
H8A H 0.315046 0.385651 0.273058 0.022 Uiso 1 1 calc R . . . .
H8B H 0.497428 0.271038 0.268007 0.022 Uiso 1 1 calc R . . . .
C9 C 0.2504(4) 0.1357(5) 0.27384(17) 0.0225(8) Uani 1 1 d . . . . .
H9A H 0.227263 0.132983 0.221125 0.027 Uiso 1 1 calc R . . . .
H9B H 0.316349 0.032686 0.287362 0.027 Uiso 1 1 calc R . . . .
C10 C 0.0641(5) 0.1446(6) 0.31356(19) 0.0234(8) Uani 1 1 d . . . . .
H10A H -0.014802 0.049048 0.299844 0.028 Uiso 1 1 calc R . . . .
H10B H -0.003084 0.246653 0.299505 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0961(5) 0.1439(5) 0.39561(18) 0.0187(7) Uani 1 1 d . . . . .
H11A H -0.025991 0.154536 0.420668 0.022 Uiso 1 1 calc R . . . .
H11B H 0.153111 0.037468 0.410102 0.022 Uiso 1 1 calc R . . . .
C12 C 0.2230(5) 0.2834(4) 0.41813(17) 0.0155(7) Uani 1 1 d . . . . .
H2 H 0.546(5) 0.168(5) 0.4385(9) 0.023 Uiso 1 1 d DR . . . .


_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 C6 1.754(3) . ?
O1 C12 1.221(4) . ?
O2 C7 1.437(4) . ?
C1 C2 1.401(5) . ?
C1 C6 1.398(5) . ?
C1 C7 1.526(5) . ?
C2 C3 1.383(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.380(5) . ?
C7 C8 1.542(4) . ?
C7 C12 1.547(4) . ?
C8 C9 1.530(5) . ?
C9 C10 1.519(5) . ?
C10 C11 1.536(4) . ?
C11 C12 1.506(5) . ?

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 C7 119.9(3) . . ?
C6 C1 C2 115.7(3) . . ?
C6 C1 C7 124.4(3) . . ?
C3 C2 C1 122.3(3) . . ?
C2 C3 C4 120.0(3) . . ?
C5 C4 C3 119.2(4) . . ?
C6 C5 C4 119.6(4) . . ?
C1 C6 Cl1 120.9(3) . . ?
C5 C6 Cl1 116.1(3) . . ?
C5 C6 C1 123.0(3) . . ?
O2 C7 C1 111.9(3) . . ?
O2 C7 C8 104.9(3) . . ?
O2 C7 C12 102.7(3) . . ?
C1 C7 C8 111.9(3) . . ?
C1 C7 C12 112.3(3) . . ?
C8 C7 C12 112.5(3) . . ?
C9 C8 C7 112.7(3) . . ?
C10 C9 C8 111.1(3) . . ?
C9 C10 C11 110.4(3) . . ?
C12 C11 C10 111.1(3) . . ?
O1 C12 C7 120.7(3) . . ?
O1 C12 C11 122.7(3) . . ?
C11 C12 C7 116.2(3) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 1.592
_oxdiff_exptl_absorpt_empirical_full_min 0.622

####################################################################### 
# 
# 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_jcm005
_database_code_depnum_ccdc_archive 'CCDC 1893726'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 Cl N O'
_chemical_formula_sum            'C13 H16 Cl N O'
_chemical_formula_weight         237.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H16 Cl N O'
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'
Cl Cl 0.3639 0.7018 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7087(3)
_cell_length_b                   8.9522(3)
_cell_length_c                   10.8050(4)
_cell_angle_alpha                76.216(3)
_cell_angle_beta                 82.767(3)
_cell_angle_gamma                72.956(3)
_cell_volume                     601.46(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6304
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.1330
_cell_measurement_theta_min      4.0340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.749
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             252
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 1 3 0.0598
4 -1 -2 0.0508
0 -2 -7 0.0848
1 2 7 0.0396
3 2 6 0.0395
1 4 -4 0.1016
2 -4 0 0.0118
-2 -2 5 0.0278
-1 -6 -2 0.0068
0 6 2 0.0734
2 5 0 0.0865
-4 -3 -4 0.1231

_exptl_crystal_size_max          0.194
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.088
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.9989 1.0026 2.9925 -0.0531 0.1346 -0.8968
3.9973 -1.0046 -1.9894 0.1021 -0.3852 0.9972
0.0035 -1.9959 -7.0018 0.0383 0.7047 0.7329
0.9957 1.9945 7.0046 -0.0346 -0.8494 -0.5408
2.9951 1.9922 6.0097 -0.0723 -1.0328 -0.0650
1.0082 4.0016 -3.9999 -0.8869 0.3520 0.3760
1.9930 -4.0034 0.0067 0.7173 -0.3624 0.5668
-2.0056 -2.0005 4.9969 0.5735 -0.2766 -0.7510
-1.0057 -5.9981 -2.0016 0.9705 0.2469 0.2652
0.0064 5.9996 1.9988 -0.9742 -0.1022 -0.4573
2.0053 4.9978 0.0040 -0.8797 -0.1980 0.1558
-3.9974 -2.9922 -4.0115 0.3364 0.9475 -0.2647

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14432
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.783
_diffrn_reflns_theta_min         4.221
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -130.00  47.00   1.00    3.00    --  -41.43   0.00  90.00  177
  2  ω    -66.00  33.00   1.00    3.00    --  -41.43  38.00 120.00   99
  3  ω     23.00  97.00   1.00    3.00    --   41.43-125.00-150.00   74
  4  ω     23.00  97.00   1.00    3.00    --   41.43-125.00  30.00   74
  5  ω     23.00  97.00   1.00    3.00    --   41.43-125.00 -90.00   74
  6  ω     37.00  92.00   1.00   15.00    --  110.38-125.00 -30.00   55
  7  ω     38.00 139.00   1.00   15.00    --  110.38 -61.00  30.00  101
  8  ω     29.00 163.00   1.00   15.00    --  110.38 -15.00 -30.00  134
  9  ω     28.00 109.00   1.00   15.00    --  110.38 -94.00  60.00   81
 10  ω     78.00 178.00   1.00   15.00    --  110.38  77.00 150.00  100
 11  ω     37.00 136.00   1.00   15.00    --  110.38 -45.00-180.00   99
 12  ω     37.00 117.00   1.00   15.00    --  110.38-125.00-120.00   80
 13  ω     82.00 178.00   1.00   15.00    --  110.38  30.00   0.00   96
 14  ω     28.00 109.00   1.00   15.00    --  110.38 -94.00   0.00   81
 15  ω   -114.00 -13.00   1.00    3.00    --  -41.43 -57.00  60.00  101
 16  ω   -114.00 -13.00   1.00    3.00    --  -41.43 -57.00 120.00  101
 17  ω   -118.00  -9.00   1.00    3.00    --  -41.43 -77.00   0.00  109
 18  ω   -118.00  -9.00   1.00    3.00    --  -41.43 -77.00-120.00  109
 19  ω     85.00 178.00   1.00   15.00    --  110.38  45.00 -90.00   93
 20  ω     85.00 178.00   1.00   15.00    --  110.38  45.00 -60.00   93
 21  ω     58.00 178.00   1.00   15.00    --  110.38  15.00 -90.00  120
 22  ω     78.00 178.00   1.00   15.00    --  110.38  77.00  30.00  100
 23  ω     58.00 178.00   1.00   15.00    --  110.38  15.00 120.00  120
 24  ω     81.00 178.00   1.00   15.00    --  110.38  61.00  90.00   97
 25  ω     81.00 178.00   1.00   15.00    --  110.38  61.00 120.00   97
 26  ω    107.00 178.00   1.00   15.00    --  110.38  77.00   0.00   71
 27  ω   -114.00 -13.00   1.00    3.00    --  -41.43 -57.00 -90.00  101
 28  ω    -31.00  70.00   1.00    3.00    --   41.43 -57.00 150.00  101
 29  ω     17.00 116.00   1.00    3.00    --   41.43  38.00  90.00   99
 30  ω      9.00 118.00   1.00    3.00    --   41.43  77.00 120.00  109
 31  ω     81.00 178.00   1.00   15.00    --  110.38  61.00  60.00   97
 32  ω     78.00 178.00   1.00   15.00    --  110.38  77.00-180.00  100
 33  ω     81.00 178.00   1.00   15.00    --  110.38  61.00   0.00   97
 34  ω     81.00 178.00   1.00   15.00    --  110.38  61.00-180.00   97
 35  ω     85.00 178.00   1.00   15.00    --  110.38  45.00-120.00   93
 36  ω     81.00 178.00   1.00   15.00    --  110.38  61.00 -30.00   97
 37  ω     81.00 178.00   1.00   15.00    --  110.38  61.00 -60.00   97
 38  ω     81.00 178.00   1.00   15.00    --  110.38  61.00 150.00   97
 39  ω     13.00 114.00   1.00    3.00    --   41.43  57.00-120.00  101
 40  ω     13.00 114.00   1.00    3.00    --   41.43  57.00  90.00  101
 41  ω      9.00 118.00   1.00    3.00    --   41.43  77.00-150.00  109
 42  ω     17.00 116.00   1.00    3.00    --   41.43  38.00-180.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0033873000
_diffrn_orient_matrix_UB_12      -0.1774154000
_diffrn_orient_matrix_UB_13      0.0450982000
_diffrn_orient_matrix_UB_21      -0.1444694000
_diffrn_orient_matrix_UB_22      0.0184297000
_diffrn_orient_matrix_UB_23      -0.1059707000
_diffrn_orient_matrix_UB_31      0.1923977000
_diffrn_orient_matrix_UB_32      -0.0459460000
_diffrn_orient_matrix_UB_33      -0.0914736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2166
_reflns_number_total             2437
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.932
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.075
_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)+(0.0698P)²+0.2641P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1236
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H3 of C3, H2 of C2, H4 of C4, H5 of C5
 At 1.5 times of:
  All C(H,H,H) groups, H1 of C11
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.34546(7) 0.35980(5) 0.52591(4) 0.03160(17) Uani 1 1 d . . . . .
O1 O 0.4167(2) 0.72174(17) 0.13052(15) 0.0341(3) Uani 1 1 d . . . . .
N1 N 0.6466(3) 0.45715(19) 0.24888(15) 0.0278(4) Uani 1 1 d . . . . .
C1 C 0.3919(3) 0.2997(2) 0.28820(18) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.3953(3) 0.2015(2) 0.2039(2) 0.0305(4) Uani 1 1 d . . . . .
H2 H 0.439857 0.230995 0.116714 0.037 Uiso 1 1 calc R . . . .
C3 C 0.3342(3) 0.0616(2) 0.2467(2) 0.0351(5) Uani 1 1 d . . . . .
H3 H 0.337870 -0.004594 0.189097 0.042 Uiso 1 1 calc R . . . .
C4 C 0.2678(3) 0.0186(2) 0.3735(2) 0.0366(5) Uani 1 1 d . . . . .
H4 H 0.222887 -0.075847 0.401983 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2664(3) 0.1123(2) 0.4595(2) 0.0324(4) Uani 1 1 d . . . . .
H5 H 0.221912 0.082219 0.546566 0.039 Uiso 1 1 calc R . . . .
C6 C 0.3311(3) 0.2508(2) 0.41581(19) 0.0279(4) Uani 1 1 d . . . . .
C7 C 0.4626(3) 0.4485(2) 0.24168(16) 0.0247(4) Uani 1 1 d . . . . .
C8 C 0.3073(3) 0.6033(2) 0.18029(18) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.1263(3) 0.6664(2) 0.27283(18) 0.0296(4) Uani 1 1 d . . . . .
H9A H 0.173753 0.713232 0.334176 0.036 Uiso 1 1 calc R . . . .
H9B H 0.064760 0.579991 0.320830 0.036 Uiso 1 1 calc R . . . .
C10 C -0.0320(3) 0.7951(2) 0.1851(2) 0.0337(4) Uani 1 1 d . . . . .
H10A H -0.012425 0.902209 0.178346 0.040 Uiso 1 1 calc R . . . .
H10B H -0.176848 0.796751 0.218530 0.040 Uiso 1 1 calc R . . . .
C11 C 0.0124(3) 0.7476(3) 0.0537(2) 0.0370(5) Uani 1 1 d . . . . .
H11A H -0.114052 0.731756 0.026402 0.044 Uiso 1 1 calc R . . . .
H11B H 0.056696 0.831748 -0.011734 0.044 Uiso 1 1 calc R . . . .
H1 H 0.536(5) 0.681(4) 0.157(3) 0.056 Uiso 1 1 d R . . . .
C12 C 0.1887(3) 0.5905(2) 0.07234(18) 0.0300(4) Uani 1 1 d . . . . .
H12A H 0.131610 0.496673 0.097458 0.036 Uiso 1 1 calc R . . . .
H12B H 0.280233 0.582428 -0.006518 0.036 Uiso 1 1 calc R . . . .
C13 C 0.8076(3) 0.3172(2) 0.3065(2) 0.0332(4) Uani 1 1 d . . . . .
H13A H 0.932102 0.301929 0.247779 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.755220 0.222443 0.323879 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.843562 0.333225 0.386647 0.050 Uiso 1 1 calc GR . . . .


_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 C6 1.7358(19) . ?
O1 C8 1.427(2) . ?
N1 C7 1.272(2) . ?
N1 C13 1.459(2) . ?
C1 C2 1.403(3) . ?
C1 C6 1.391(3) . ?
C1 C7 1.498(3) . ?
C2 C3 1.389(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.389(3) . ?
C5 C6 1.391(3) . ?
C7 C8 1.529(2) . ?
C8 C9 1.534(3) . ?
C8 C12 1.535(2) . ?
C9 C10 1.539(2) . ?
C10 C11 1.547(3) . ?
C11 C12 1.539(3) . ?

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
C7 N1 C13 120.84(17) . . ?
C2 C1 C7 120.13(17) . . ?
C6 C1 C2 118.20(18) . . ?
C6 C1 C7 121.60(16) . . ?
C3 C2 C1 120.6(2) . . ?
C4 C3 C2 119.95(19) . . ?
C3 C4 C5 120.64(19) . . ?
C4 C5 C6 118.8(2) . . ?
C1 C6 Cl1 119.73(14) . . ?
C1 C6 C5 121.75(18) . . ?
C5 C6 Cl1 118.47(16) . . ?
N1 C7 C1 124.69(17) . . ?
N1 C7 C8 116.00(16) . . ?
C1 C7 C8 119.31(15) . . ?
O1 C8 C7 108.71(15) . . ?
O1 C8 C9 109.51(16) . . ?
O1 C8 C12 108.19(15) . . ?
C7 C8 C9 113.37(15) . . ?
C7 C8 C12 115.44(15) . . ?
C9 C8 C12 101.31(15) . . ?
C8 C9 C10 103.84(15) . . ?
C9 C10 C11 105.42(16) . . ?
C12 C11 C10 105.74(15) . . ?
C8 C12 C11 103.09(16) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 2.390
_oxdiff_exptl_absorpt_empirical_full_min 0.370

####################################################################### 
# 
# 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_jcm007
_database_code_depnum_ccdc_archive 'CCDC 1893727'
loop_
_audit_author_name
_audit_author_address
'Kristof Van Hecke'
;Ghent University
Belgium
;
_audit_update_record             
;
2019-01-26 deposited with the CCDC.	2019-03-19 downloaded from the CCDC.
;
_audit_creation_date             2019-01-23
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 Cl N O'
_chemical_formula_sum            'C13 H16 Cl N O'
_chemical_formula_weight         237.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H16 Cl N O'
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'
Cl Cl 0.3639 0.7018 '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'

_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                   10.0679(3)
_cell_length_b                   8.2104(3)
_cell_length_c                   28.6875(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.842(3)
_cell_angle_gamma                90
_cell_volume                     2343.17(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9000
_cell_measurement_temperature    100.0(1)
_cell_measurement_theta_max      75.2100
_cell_measurement_theta_min      3.0850
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.696
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.738
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -18 0.0496
0 -1 18 0.0148
-6 2 2 0.1543
5 -2 6 0.1180
1 -5 -6 0.0440
6 0 -5 0.1316
4 4 2 0.1109
-5 -3 0 0.1088
0 5 5 0.0658

_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.064
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0073 1.0087 -17.9888 -0.3102 0.9400 0.1129
0.0073 -1.0087 17.9888 0.3102 -0.9400 -0.1129
-6.0026 1.9988 2.0009 -0.1107 0.1913 -0.9677
5.0051 -2.0027 5.9948 0.2078 -0.5612 0.7532
1.0027 -4.9976 -6.0127 0.8109 0.3370 0.4722
5.9996 0.0028 -4.9931 -0.2686 -0.0615 0.8852
3.9979 3.9998 2.0151 -0.8548 -0.3824 0.3192
-4.9984 -3.0007 -0.0135 0.7294 0.3162 -0.5329
-0.0029 4.9982 5.0139 -0.8568 -0.3384 -0.3231

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21941
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.393
_diffrn_reflns_theta_min         3.118
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.0(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -125.00 -41.00   1.00    6.00    --  -41.68-170.00  90.00   84
  2  ω   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00 -90.00   99
  3  ω   -116.00 -17.00   1.00    6.00    --  -41.68 -38.00  30.00   99
  4  ω     23.00  98.00   1.00    6.00    --   41.68-125.00-180.00   75
  5  ω     77.00 178.00   1.00   15.00    --  109.13  77.00  30.00  101
  6  ω     94.00 178.00   1.00   15.00    --  109.13 125.00-150.00   84
  7  ω     81.00 178.00   1.00   15.00    --  109.13  30.00-120.00   97
  8  ω     94.00 178.00   1.00   15.00    --  109.13 125.00 -30.00   84
  9  ω     33.00 142.00   1.00   15.00    --  109.13 -77.00 120.00  109
 10  ω     77.00 178.00   1.00   15.00    --  109.13  77.00 150.00  101
 11  ω   -118.00  -9.00   1.00    6.00    --  -41.68 -77.00-120.00  109
 12  ω   -115.00 -14.00   1.00    6.00    --  -41.68 -57.00 150.00  101
 13  ω     64.00 124.00   1.00    6.00    --   41.68 170.00 106.00   60
 14  ω     26.00 110.00   1.00   15.00    --  109.13 -94.00 -60.00   84
 15  ω     81.00 178.00   1.00   15.00    --  109.13  30.00 -30.00   97
 16  ω     83.00 178.00   1.00   15.00    --  109.13  45.00 -90.00   95
 17  ω     83.00 152.00   1.00   15.00    --  109.13  45.00   0.00   69
 18  ω     77.00 178.00   1.00   15.00    --  109.13  77.00  90.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0386645000
_diffrn_orient_matrix_UB_12      -0.1787139000
_diffrn_orient_matrix_UB_13      0.0072383000
_diffrn_orient_matrix_UB_21      -0.0543941000
_diffrn_orient_matrix_UB_22      -0.0145145000
_diffrn_orient_matrix_UB_23      -0.0530475000
_diffrn_orient_matrix_UB_31      0.1397278000
_diffrn_orient_matrix_UB_32      -0.0551028000
_diffrn_orient_matrix_UB_33      -0.0094247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4100
_reflns_number_total             4776
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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         0.432
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4776
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0423
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.3768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1183
_refine_ls_wR_factor_ref         0.1261
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H4,H1,H2A} of C4, All C(H,H) groups
 At 1.5 times of:
  {H26A,H26B,H26C} of C26, {H13A,H13B,H13C} of C13
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C22(H22A,H22B),
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C17(H17), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.11123(4) 0.32634(5) 0.32104(2) 0.02685(13) Uani 1 1 d . . . . .
O1 O -0.08479(11) 0.44411(13) 0.42481(4) 0.0224(2) Uani 1 1 d . . . . .
N1 N 0.19706(13) 0.59472(16) 0.42923(4) 0.0197(3) Uani 1 1 d . . . . .
C1 C 0.03608(15) 0.59748(19) 0.35221(5) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.07261(16) 0.75896(19) 0.34499(5) 0.0220(3) Uani 1 1 d . . . . .
H2 H 0.142534 0.807272 0.366584 0.026 Uiso 1 1 calc R . . . .
C3 C 0.00978(17) 0.8508(2) 0.30723(6) 0.0273(3) Uani 1 1 d . . . . .
H3 H 0.036935 0.960127 0.303248 0.033 Uiso 1 1 calc R . . . .
C4 C -0.09260(17) 0.7825(2) 0.27540(5) 0.0291(4) Uani 1 1 d . . . . .
H4 H -0.136564 0.845453 0.249791 0.035 Uiso 1 1 calc R . . . .
H1 H 0.266(2) 0.640(3) 0.4200(7) 0.035 Uiso 1 1 d R . . . .
H2A H 0.757(2) 0.630(3) 0.4285(7) 0.035 Uiso 1 1 d R . . . .
C5 C -0.13079(16) 0.6224(2) 0.28096(5) 0.0283(4) Uani 1 1 d . . . . .
H5 H -0.200839 0.574874 0.259242 0.034 Uiso 1 1 calc R . . . .
C6 C -0.06542(15) 0.5317(2) 0.31872(5) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.11747(14) 0.49826(18) 0.39231(5) 0.0172(3) Uani 1 1 d . . . . .
C8 C 0.02727(14) 0.39845(17) 0.42073(5) 0.0177(3) Uani 1 1 d . . . . .
C9 C 0.09115(15) 0.25373(18) 0.44820(5) 0.0211(3) Uani 1 1 d . . . . .
H9A H 0.019139 0.182033 0.456411 0.025 Uiso 1 1 calc R . . . .
H9B H 0.143938 0.293100 0.478044 0.025 Uiso 1 1 calc R . . . .
C10 C 0.18331(16) 0.15366(19) 0.42145(6) 0.0244(3) Uani 1 1 d . . . . .
H10A H 0.229603 0.069050 0.442564 0.029 Uiso 1 1 calc R . . . .
H10B H 0.128830 0.098365 0.394350 0.029 Uiso 1 1 calc R . . . .
C11 C 0.28713(16) 0.26286(19) 0.40376(5) 0.0233(3) Uani 1 1 d . . . . .
H11A H 0.347415 0.196126 0.387287 0.028 Uiso 1 1 calc R . . . .
H11B H 0.342487 0.317123 0.430858 0.028 Uiso 1 1 calc R . . . .
C12 C 0.21718(15) 0.39126(19) 0.37001(5) 0.0215(3) Uani 1 1 d . . . . .
H12A H 0.168100 0.335950 0.341857 0.026 Uiso 1 1 calc R . . . .
H12B H 0.286179 0.462226 0.359392 0.026 Uiso 1 1 calc R . . . .
C13 C 0.12631(16) 0.70576(19) 0.45666(5) 0.0236(3) Uani 1 1 d . . . . .
H13A H 0.057376 0.765138 0.435427 0.035 Uiso 1 1 calc GR . . . .
H13B H 0.190406 0.783335 0.473534 0.035 Uiso 1 1 calc GR . . . .
H13C H 0.083627 0.643366 0.479440 0.035 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.39789(4) 0.94611(5) 0.32128(2) 0.02600(13) Uani 1 1 d . . . . .
O2 O 0.41287(10) 0.84290(13) 0.42520(4) 0.0222(2) Uani 1 1 d . . . . .
N2 N 0.68783(13) 0.67680(15) 0.43546(4) 0.0201(3) Uani 1 1 d . . . . .
C14 C 0.44209(15) 0.73987(19) 0.32038(5) 0.0218(3) Uani 1 1 d . . . . .
C15 C 0.53883(14) 0.67365(18) 0.35553(5) 0.0188(3) Uani 1 1 d . . . . .
C16 C 0.57534(15) 0.51180(19) 0.34914(5) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.642266 0.463016 0.371807 0.026 Uiso 1 1 calc R . . . .
C17 C 0.51678(16) 0.4199(2) 0.31064(6) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.543940 0.310283 0.307275 0.031 Uiso 1 1 calc R . . . .
C18 C 0.41869(16) 0.4887(2) 0.27720(5) 0.0265(3) Uani 1 1 d . . . . .
H18 H 0.377616 0.425955 0.251085 0.032 Uiso 1 1 calc R . . . .
C19 C 0.38082(16) 0.6494(2) 0.28205(5) 0.0267(3) Uani 1 1 d . . . . .
H19 H 0.313513 0.697379 0.259355 0.032 Uiso 1 1 calc R . . . .
C20 C 0.61761(14) 0.77302(17) 0.39613(5) 0.0170(3) Uani 1 1 d . . . . .
C21 C 0.52693(14) 0.88251(17) 0.42181(5) 0.0177(3) Uani 1 1 d . . . . .
C22 C 0.59258(15) 1.02891(18) 0.44800(5) 0.0210(3) Uani 1 1 d . . . . .
H22A H 0.642230 0.992358 0.478693 0.025 Uiso 1 1 calc R . . . .
H22B H 0.521526 1.105161 0.454532 0.025 Uiso 1 1 calc R . . . .
C23 C 0.68945(16) 1.11974(19) 0.42111(5) 0.0238(3) Uani 1 1 d . . . . .
H23A H 0.638815 1.169844 0.392357 0.029 Uiso 1 1 calc R . . . .
H23B H 0.734733 1.207821 0.441122 0.029 Uiso 1 1 calc R . . . .
C24 C 0.79410(16) 1.00226(19) 0.40744(5) 0.0239(3) Uani 1 1 d . . . . .
H24A H 0.844337 0.951642 0.436183 0.029 Uiso 1 1 calc R . . . .
H24B H 0.858906 1.062490 0.391224 0.029 Uiso 1 1 calc R . . . .
C25 C 0.72546(15) 0.87007(19) 0.37487(5) 0.0220(3) Uani 1 1 d . . . . .
H25A H 0.794688 0.793317 0.367120 0.026 Uiso 1 1 calc R . . . .
H25B H 0.682791 0.921329 0.345063 0.026 Uiso 1 1 calc R . . . .
C26 C 0.60806(16) 0.56795(19) 0.46052(5) 0.0237(3) Uani 1 1 d . . . . .
H26A H 0.551662 0.498513 0.437742 0.036 Uiso 1 1 calc GR . . . .
H26B H 0.550803 0.632704 0.478154 0.036 Uiso 1 1 calc GR . . . .
H26C H 0.668241 0.499685 0.482469 0.036 Uiso 1 1 calc GR . . . .


_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 C6 1.7518(17) . ?
O1 C8 1.2114(19) . ?
N1 C7 1.4596(18) . ?
N1 C13 1.459(2) . ?
C1 C2 1.400(2) . ?
C1 C6 1.399(2) . ?
C1 C7 1.5391(19) . ?
C2 C3 1.390(2) . ?
C3 C4 1.386(2) . ?
C4 C5 1.386(3) . ?
C5 C6 1.393(2) . ?
C7 C8 1.5456(19) . ?
C7 C12 1.545(2) . ?
C8 C9 1.513(2) . ?
C9 C10 1.531(2) . ?
C10 C11 1.522(2) . ?
C11 C12 1.528(2) . ?
Cl2 C14 1.7521(16) . ?
O2 C21 1.2117(19) . ?
N2 C20 1.4670(17) . ?
N2 C26 1.462(2) . ?
C14 C15 1.400(2) . ?
C14 C19 1.390(2) . ?
C15 C16 1.398(2) . ?
C15 C20 1.5384(19) . ?
C16 C17 1.392(2) . ?
C17 C18 1.387(2) . ?
C18 C19 1.387(3) . ?
C20 C21 1.5463(19) . ?
C20 C25 1.546(2) . ?
C21 C22 1.5144(19) . ?
C22 C23 1.528(2) . ?
C23 C24 1.523(2) . ?
C24 C25 1.526(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
C13 N1 C7 118.11(12) . . ?
C2 C1 C7 119.35(13) . . ?
C6 C1 C2 116.43(13) . . ?
C6 C1 C7 123.89(14) . . ?
C3 C2 C1 122.06(15) . . ?
C4 C3 C2 119.81(16) . . ?
C3 C4 C5 119.95(15) . . ?
C4 C5 C6 119.35(15) . . ?
C1 C6 Cl1 120.96(12) . . ?
C5 C6 Cl1 116.62(12) . . ?
C5 C6 C1 122.36(15) . . ?
N1 C7 C1 115.15(12) . . ?
N1 C7 C8 101.91(11) . . ?
N1 C7 C12 106.85(11) . . ?
C1 C7 C8 112.74(11) . . ?
C1 C7 C12 107.26(11) . . ?
C12 C7 C8 112.88(12) . . ?
O1 C8 C7 121.22(13) . . ?
O1 C8 C9 121.35(13) . . ?
C9 C8 C7 116.99(12) . . ?
C8 C9 C10 113.71(12) . . ?
C11 C10 C9 110.56(12) . . ?
C10 C11 C12 110.13(12) . . ?
C11 C12 C7 113.30(12) . . ?
C26 N2 C20 118.11(12) . . ?
C15 C14 Cl2 120.99(12) . . ?
C19 C14 Cl2 116.44(12) . . ?
C19 C14 C15 122.51(15) . . ?
C14 C15 C20 124.06(13) . . ?
C16 C15 C14 116.26(13) . . ?
C16 C15 C20 119.20(13) . . ?
C17 C16 C15 122.10(14) . . ?
C18 C17 C16 119.87(15) . . ?
C19 C18 C17 119.72(14) . . ?
C18 C19 C14 119.49(15) . . ?
N2 C20 C15 115.34(12) . . ?
N2 C20 C21 101.34(11) . . ?
N2 C20 C25 107.23(11) . . ?
C15 C20 C21 113.30(11) . . ?
C15 C20 C25 106.65(11) . . ?
C25 C20 C21 112.97(12) . . ?
O2 C21 C20 121.23(13) . . ?
O2 C21 C22 121.33(13) . . ?
C22 C21 C20 116.94(12) . . ?
C21 C22 C23 113.63(12) . . ?
C24 C23 C22 109.96(13) . . ?
C23 C24 C25 109.98(12) . . ?
C24 C25 C20 113.86(12) . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a nylon loop'
_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 4.256
_oxdiff_exptl_absorpt_empirical_full_min 0.501

