# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_rja230012_fa
_database_code_depnum_ccdc_archive 'CCDC 2307639'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-03-01
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Cl N O2'
_chemical_formula_sum            'C18 H20 Cl N O2'
_chemical_formula_weight         317.80
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H20 Cl1 N1 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'
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                   8.35130(10)
_cell_length_b                   13.4596(2)
_cell_length_c                   15.5830(2)
_cell_angle_alpha                77.9650(10)
_cell_angle_beta                 76.1000(10)
_cell_angle_gamma                77.2070(10)
_cell_volume                     1635.64(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    24066
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      78.2000
_cell_measurement_theta_min      3.0010
_shelx_estimated_absorpt_T_max   0.902
_shelx_estimated_absorpt_T_min   0.599
_exptl_absorpt_coefficient_mu    2.116
_exptl_absorpt_correction_T_max  0.901
_exptl_absorpt_correction_T_min  0.701
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'rect. Prism'
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0150
0 0 1 0.0360
1 0 0 0.1232
-1 0 0 0.1192
0 -1 0 0.0420
0 1 0 0.0420
1 1 0 0.1144
-1 -1 0 0.1104

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
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
0.0004 -0.0010 -0.9993 0.0121 0.1023 0.0059
-0.0004 0.0010 0.9993 -0.0121 -0.1023 -0.0059
1.0002 -0.0007 -0.0019 0.0492 0.0234 0.1855
-1.0002 0.0007 0.0019 -0.0492 -0.0234 -0.1855
0.0008 -0.9977 -0.0000 0.1141 -0.0328 -0.0036
-0.0008 0.9977 0.0000 -0.1141 0.0328 0.0036
0.9993 0.9970 -0.0019 -0.0649 0.0562 0.1891
-0.9993 -0.9970 0.0019 0.0649 -0.0562 -0.1891

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.914
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            43178
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.583
_diffrn_reflns_theta_min         2.961
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  70.00   0.50    0.26    --   48.76-143.00  55.00   62
  2  ω     50.00  75.00   0.50    0.26    --   96.11-143.00  55.00   50
  3  ω     49.00 125.00   0.50    0.26    --  108.00-143.00  55.00  152
  4  ω     36.00  61.00   0.50    0.26    --   48.76-128.00-133.00   50
  5  ω     50.00  75.00   0.50    0.26    --  108.00-128.00-133.00   50
  6  ω     62.00 110.00   0.50    0.26    --  108.00-125.00-180.00   96
  7  ω     61.00  98.00   0.50    0.26    --  108.00 -77.00-180.00   74
  8  ω     25.00  65.00   0.50    0.26    --   96.11 -61.00-150.00   80
  9  ω     42.00  69.00   0.50    0.26    --  108.00 -61.00-120.00   54
 10  ω     48.00  96.00   0.50    0.26    --  108.00 -77.00  30.00   96
 11  ω     35.00  61.00   0.50    0.26    --  108.00 -61.00   0.00   52
 12  ω     34.00  59.00   0.50    0.26    --  108.00 -61.00  60.00   50
 13  ω     91.00 116.00   0.50    0.26    --   96.11 143.00 111.00   50
 14  ω     92.00 117.00   0.50    0.26    --  108.00 143.00 111.00   50
 15  ω    101.00 126.00   0.50    0.26    --  108.00 128.00 -59.00   50
 16  ω    111.00 136.00   0.50    0.26    --   96.11 128.00 -59.00   50
 17  ω     40.00  66.00   0.50    0.26    --   62.00  71.00 -32.16   52
 18  ω     31.00  56.00   0.50    0.26    --   58.00  77.00 -88.43   50
 19  ω     32.00  58.00   0.50    0.26    --   58.00  77.00-119.04   52
 20  ω     31.00  56.00   0.50    0.26    --   58.00  77.00-170.46   50
 21  ω     70.00 154.00   0.50    0.26    --   96.11  77.00-180.00  168
 22  ω     85.00 111.00   0.50    0.26    --   58.00  77.00-119.04   52
 23  ω     33.00  62.00   0.50    0.26    --   58.00  76.00  21.19   58
 24  ω     36.00  62.00   0.50    0.26    --   62.00  76.00 156.91   52
 25  ω     31.00  57.00   0.50    0.26    --   58.00  77.00  85.57   52
 26  ω     69.00 126.00   0.50    0.26    --   58.00  77.00  85.57  114
 27  ω     96.00 122.00   0.50    0.26    --   62.00  75.00-156.55   52
 28  ω     38.00  64.00   0.50    0.26    --   62.00  75.00-156.55   52
 29  ω     38.00  64.00   0.50    0.26    --   58.00  75.00 -13.56   52
 30  ω     17.00  42.00   0.50    0.26    --   50.00  88.00  11.25   50
 31  ω     62.00 105.00   0.50    0.26    --   48.76 143.00 111.00   86
 32  ω    -43.00 -13.00   0.50    0.26    --   10.00 124.00 123.79   60
 33  ω    -25.00   1.00   0.50    0.26    --   18.00 104.00  45.42   52
 34  ω     15.00  41.00   0.50    0.26    --   50.00  92.00  43.29   52
 35  ω     16.00  42.00   0.50    0.26    --   50.00  91.00 111.83   52
 36  ω     -6.00  22.00   0.50    0.26    --   34.00 100.00 145.25   56
 37  ω    -60.00 -31.00   0.50    0.26    --   18.00 160.00 -46.45   58
 38  ω    -60.00 -33.00   0.50    0.26    --   18.00 162.00-116.83   54
 39  ω     16.00  41.00   0.50    0.26    --   50.00  89.00-129.59   50
 40  ω     17.00  42.00   0.50    0.26    --   50.00  88.00 -52.42   50
 41  ω   -110.00 -59.00   0.50    0.26    --  -49.76 143.00 111.00  102
 42  ω   -117.00 -73.00   0.50    0.26    --  -92.01 143.00 111.00   88
 43  ω    -85.00 -60.00   0.50    0.26    --  -49.76 128.00 -59.00   50
 44  ω    -90.00 -65.00   0.50    0.26    --  -92.01 128.00 -59.00   50
 45  ω   -104.00 -29.00   0.50    0.26    --  -92.01  77.00 -30.00  150
 46  ω    -48.00 -21.00   0.50    0.26    --  -92.01  45.00 -30.00   54
 47  ω   -105.00 -23.00   0.50    0.26    --  -92.01  77.00 120.00  164
 48  ω    -90.00 -64.00   0.50    0.26    --  -90.00 -77.00  97.03   52
 49  ω   -145.00 -67.00   0.50    0.26    --  -92.01 -77.00  90.00  156
 50  ω   -130.00 -92.00   0.50    0.26    --  -62.00 -77.00  71.40   76
 51  ω    -74.00 -35.00   0.50    0.26    --  -62.00 -77.00  71.40   78
 52  ω    -91.00 -66.00   0.50    0.26    --  -92.01 -77.00  30.00   50
 53  ω   -156.00 -65.00   0.50    0.26    --  -92.01 -77.00 -30.00  182
 54  ω   -141.00-116.00   0.50    0.26    --  -92.01 -77.00  30.00   50
 55  ω   -160.00 -65.00   0.50    0.26    --  -92.01 -77.00 -60.00  190
 56  ω   -160.00 -99.00   0.50    0.26    --  -92.01 -77.00 -90.00  122
 57  ω    -92.00 -66.00   0.50    0.26    --  -92.01 -77.00 -90.00   52
 58  ω   -126.00 -66.00   0.50    0.26    --  -92.01 -77.00-120.00  120
 59  ω   -146.00-103.00   0.50    0.26    --  -78.00 -76.00  46.39   86
 60  ω   -159.00 -67.00   0.50    0.26    --  -92.01 -77.00  60.00  184
 61  ω    -75.00 -48.00   0.50    0.26    --  -74.00 -75.00  52.28   54
 62  ω    -98.00 -53.00   0.50    0.26    --  -78.00 -76.00  46.39   90
 63  ω    -92.00 -67.00   0.50    0.26    --  -92.01 -77.00 120.00   50
 64  ω   -160.00 -97.00   0.50    0.26    --  -92.01 -77.00 120.00  126
 65  ω   -148.00-122.00   0.50    0.26    --  -82.00 -74.00 -13.32   52
 66  ω    -85.00 -57.00   0.50    0.26    --  -82.00 -73.00 108.80   56
 67  ω    -94.00 -62.00   0.50    0.26    --  -86.00 -71.00  24.43   64
 68  ω    -76.00 -51.00   0.50    0.26    --  -74.00 -68.00 134.33   50
 69  ω    -95.00 -43.00   0.50    0.26    --  -66.00 -70.00 -22.03  104
 70  ω    -91.00 -57.00   0.50    0.26    --  -82.00 -74.00 -13.32   68
 71  ω   -103.00 -68.00   0.50    0.26    --  -90.00 -70.00-166.42   70
 72  ω   -165.00 -79.00   0.50    0.26    --  -99.00 -69.00  13.30  172
 73  ω    -82.00 -56.00   0.50    0.26    --  -78.00 -67.00 119.62   52
 74  ω    -87.00 -61.00   0.50    0.26    --  -82.00 -67.00 113.95   52
 75  ω    -84.00 -57.00   0.50    0.26    --  -78.00 -67.00 155.09   54
 76  ω   -159.00 -68.00   0.50    0.26    --  -90.00 -67.00 148.18  182
 77  ω    -88.00 -58.00   0.50    0.26    --  -78.00 -66.00  -9.30   60
 78  ω    -88.00 -57.00   0.50    0.26    --  -78.00 -64.00 -54.56   62
 79  ω    -88.00 -53.00   0.50    0.26    --  -74.00 -64.00 -91.18   70
 80  ω    -77.00 -51.00   0.50    0.26    --  -70.00 -65.00-122.51   52
 81  ω    -77.00 -52.00   0.50    0.26    --  -74.00 -66.00-175.07   50
 82  ω    -83.00 -57.00   0.50    0.26    --  -78.00 -64.00-147.16   52
 83  ω    -82.00 -57.00   0.50    0.26    --  -78.00 -64.00-105.81   50
 84  ω    -91.00 -65.00   0.50    0.26    --  -86.00 -64.00-165.72   52
 85  ω   -137.00-111.00   0.50    0.26    --  -74.00 -66.00-175.07   52
 86  ω   -130.00-105.00   0.50    0.26    --  -74.00 -64.00 -91.18   50
 87  ω   -151.00 -92.00   0.50    0.26    --  -78.00 -64.00 -54.56  118
 88  ω   -153.00 -66.00   0.50    0.26    --  -86.00 -64.00 169.97  174
 89  ω   -116.00 -91.00   0.50    0.26    --  -49.76-143.00  55.00   50
 90  ω   -149.00 -69.00   0.50    0.26    --  -92.01-143.00  55.00  160
 91  ω   -158.00 -88.00   0.50    0.26    --  -92.01-128.00-133.00  140
 92  ω   -122.00 -97.00   0.50    0.26    --  -49.76-128.00-133.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0490667000
_diffrn_orient_matrix_UB_12      -0.1142968000
_diffrn_orient_matrix_UB_13      -0.0119878000
_diffrn_orient_matrix_UB_21      0.0232364000
_diffrn_orient_matrix_UB_22      0.0328562000
_diffrn_orient_matrix_UB_23      -0.1023762000
_diffrn_orient_matrix_UB_31      0.1854236000
_diffrn_orient_matrix_UB_32      0.0037529000
_diffrn_orient_matrix_UB_33      -0.0058882000
_diffrn_oxdiff_digest_frames     
;
01c2c86d7b77daaf35a4fa164a9d555191071369aa8
;
_diffrn_oxdiff_digest_hkl        
;
011763e7b29138f8e8fcfb12b4ceda38baa0ca
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5831
_reflns_number_total             6442
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.458
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         6442
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.065
_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)+(0.0547P)²+0.7011P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14),
 C21(H21), C22(H22), C24(H24), C25(H25), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,
 H18C), C26(H26A,H26B,H26C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C36(H36A,
 H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.48164(5) 0.77095(3) 0.92612(3) 0.03349(12) Uani 1 1 d . . . . .
Cl2 Cl 0.57535(5) 0.42719(3) 0.68538(3) 0.03712(12) Uani 1 1 d . . . . .
O1 O 0.39370(16) 0.60901(9) 0.77927(9) 0.0391(3) Uani 1 1 d . . . . .
O2 O 1.04447(15) 0.37994(9) 0.92633(9) 0.0374(3) Uani 1 1 d . . . . .
O3 O 0.85631(15) 0.17335(9) 0.73618(9) 0.0401(3) Uani 1 1 d . . . . .
O4 O 0.14474(15) 0.10131(10) 0.95074(8) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.43413(17) 0.74403(10) 0.83148(9) 0.0299(3) Uani 1 1 d . . . . .
N2 N 0.72399(17) 0.31822(10) 0.66248(9) 0.0307(3) Uani 1 1 d . . . . .
C00Y C 0.8590(2) 0.27974(14) 0.47330(12) 0.0370(4) Uani 1 1 d . . . . .
C1 C 0.4754(2) 0.64088(12) 0.81887(11) 0.0311(3) Uani 1 1 d . . . . .
C2 C 0.6288(2) 0.57759(12) 0.84833(11) 0.0304(3) Uani 1 1 d . . . . .
C3 C 0.7792(2) 0.61337(13) 0.83095(11) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.783763 0.682728 0.802761 0.039 Uiso 1 1 calc R U . . .
C4 C 0.9234(2) 0.54941(13) 0.85412(11) 0.0318(4) Uani 1 1 d . . . . .
H4 H 1.026345 0.574025 0.840235 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9143(2) 0.44921(12) 0.89779(11) 0.0301(3) Uani 1 1 d . . . . .
C6 C 0.7640(2) 0.41275(13) 0.91561(11) 0.0322(4) Uani 1 1 d . . . . .
H6 H 0.758593 0.344075 0.945541 0.039 Uiso 1 1 calc R U . . .
C7 C 0.6233(2) 0.47544(13) 0.89019(11) 0.0319(4) Uani 1 1 d . . . . .
H7 H 0.522231 0.449291 0.901093 0.038 Uiso 1 1 calc R U . . .
C8 C 1.2037(2) 0.41192(14) 0.90676(13) 0.0383(4) Uani 1 1 d . . . . .
H8A H 1.239865 0.430436 0.841761 0.057 Uiso 1 1 calc R U . . .
H8B H 1.286482 0.355258 0.929805 0.057 Uiso 1 1 calc R U . . .
H8C H 1.193660 0.471971 0.935320 0.057 Uiso 1 1 calc R U . . .
C9 C 0.2770(2) 0.80553(12) 0.81235(11) 0.0294(3) Uani 1 1 d . . . . .
C10 C 0.2761(2) 0.89223(12) 0.74396(11) 0.0305(3) Uani 1 1 d . . . . .
C11 C 0.1167(2) 0.94815(13) 0.73524(13) 0.0372(4) Uani 1 1 d . . . . .
H11 H 0.108663 1.008145 0.690730 0.045 Uiso 1 1 calc R U . . .
C12 C -0.0295(2) 0.92004(14) 0.78848(14) 0.0412(4) Uani 1 1 d . . . . .
H12 H -0.134724 0.960815 0.780092 0.049 Uiso 1 1 calc R U . . .
C13 C -0.0239(2) 0.83324(15) 0.85372(13) 0.0396(4) Uani 1 1 d . . . . .
H13 H -0.124269 0.813070 0.889751 0.048 Uiso 1 1 calc R U . . .
C14 C 0.1307(2) 0.77640(14) 0.86543(12) 0.0349(4) Uani 1 1 d . . . . .
H14 H 0.137002 0.716698 0.910329 0.042 Uiso 1 1 calc R U . . .
C15 C 0.4355(2) 0.92506(13) 0.68120(11) 0.0324(4) Uani 1 1 d . . . . .
C16 C 0.3928(3) 1.02471(14) 0.61595(13) 0.0414(4) Uani 1 1 d . . . . .
H16A H 0.318228 1.014193 0.580033 0.062 Uiso 1 1 calc R U . . .
H16B H 0.496148 1.042763 0.576286 0.062 Uiso 1 1 calc R U . . .
H16C H 0.336623 1.080840 0.649869 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5558(2) 0.94518(14) 0.73354(12) 0.0380(4) Uani 1 1 d . . . . .
H17A H 0.494491 0.992709 0.775158 0.057 Uiso 1 1 calc R U . . .
H17B H 0.646535 0.975862 0.691580 0.057 Uiso 1 1 calc R U . . .
H17C H 0.603169 0.879813 0.767317 0.057 Uiso 1 1 calc R U . . .
C18 C 0.5269(2) 0.84023(14) 0.62459(12) 0.0388(4) Uani 1 1 d . . . . .
H18A H 0.555955 0.775248 0.664373 0.058 Uiso 1 1 calc R U . . .
H18B H 0.629402 0.860665 0.585819 0.058 Uiso 1 1 calc R U . . .
H18C H 0.453346 0.830835 0.587590 0.058 Uiso 1 1 calc R U . . .
C19 C 0.7238(2) 0.23137(13) 0.72983(11) 0.0319(4) Uani 1 1 d . . . . .
C20 C 0.5616(2) 0.20736(12) 0.78547(11) 0.0309(3) Uani 1 1 d . . . . .
C21 C 0.4139(2) 0.22567(12) 0.75401(11) 0.0322(4) Uani 1 1 d . . . . .
H21 H 0.410734 0.262801 0.695300 0.039 Uiso 1 1 calc R U . . .
C22 C 0.2712(2) 0.19126(13) 0.80590(11) 0.0321(4) Uani 1 1 d . . . . .
H22 H 0.172144 0.203083 0.782663 0.039 Uiso 1 1 calc R U . . .
C23 C 0.2749(2) 0.13908(13) 0.89264(11) 0.0317(4) Uani 1 1 d . . . . .
C24 C 0.4222(2) 0.12092(13) 0.92592(11) 0.0321(4) Uani 1 1 d . . . . .
H24 H 0.424006 0.086334 0.985506 0.039 Uiso 1 1 calc R U . . .
C25 C 0.5640(2) 0.15308(13) 0.87244(11) 0.0322(4) Uani 1 1 d . . . . .
H25 H 0.664630 0.138400 0.894605 0.039 Uiso 1 1 calc R U . . .
C26 C -0.0109(2) 0.11968(15) 0.92219(14) 0.0412(4) Uani 1 1 d . . . . .
H26A H 0.002557 0.083308 0.871865 0.062 Uiso 1 1 calc R U . . .
H26B H -0.045528 0.193952 0.903174 0.062 Uiso 1 1 calc R U . . .
H26C H -0.096648 0.094375 0.971919 0.062 Uiso 1 1 calc R U . . .
C27 C 0.8845(2) 0.34356(12) 0.61470(11) 0.0304(3) Uani 1 1 d . . . . .
C29 C 1.1078(2) 0.35291(14) 0.48793(14) 0.0409(4) Uani 1 1 d . . . . .
H29 H 1.157610 0.342920 0.428064 0.049 Uiso 1 1 calc R U . . .
C30 C 1.1938(2) 0.39357(15) 0.53439(15) 0.0441(5) Uani 1 1 d . . . . .
H30 H 1.300803 0.410319 0.506070 0.053 Uiso 1 1 calc R U . . .
C31 C 1.1253(2) 0.40993(14) 0.62148(14) 0.0425(4) Uani 1 1 d . . . . .
H31 H 1.183933 0.437960 0.653190 0.051 Uiso 1 1 calc R U . . .
C32 C 0.9705(2) 0.38482(14) 0.66120(12) 0.0376(4) Uani 1 1 d . . . . .
H32 H 0.921659 0.395686 0.720945 0.045 Uiso 1 1 calc R U . . .
C33 C 0.9495(2) 0.32599(13) 0.52642(12) 0.0331(4) Uani 1 1 d . . . . .
C34 C 0.9507(3) 0.28232(18) 0.37499(14) 0.0515(5) Uani 1 1 d . . . . .
H34A H 0.960677 0.353651 0.347288 0.077 Uiso 1 1 calc R U . . .
H34B H 0.887145 0.255166 0.342660 0.077 Uiso 1 1 calc R U . . .
H34C H 1.062857 0.239771 0.372316 0.077 Uiso 1 1 calc R U . . .
C35 C 0.6800(2) 0.34139(15) 0.47229(13) 0.0408(4) Uani 1 1 d . . . . .
H35A H 0.609252 0.328643 0.532080 0.061 Uiso 1 1 calc R U . . .
H35B H 0.633214 0.319413 0.428845 0.061 Uiso 1 1 calc R U . . .
H35C H 0.683872 0.415272 0.455305 0.061 Uiso 1 1 calc R U . . .
C36 C 0.8526(3) 0.16624(15) 0.51476(15) 0.0489(5) Uani 1 1 d . . . . .
H36A H 0.966514 0.128480 0.517330 0.073 Uiso 1 1 calc R U . . .
H36B H 0.803567 0.135239 0.477906 0.073 Uiso 1 1 calc R U . . .
H36C H 0.783725 0.162624 0.575485 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7410(14) . ?
Cl2 N2 1.7373(14) . ?
O1 C1 1.214(2) . ?
O2 C5 1.363(2) . ?
O2 C8 1.432(2) . ?
O3 C19 1.217(2) . ?
O4 C23 1.357(2) . ?
O4 C26 1.428(2) . ?
N1 C1 1.398(2) . ?
N1 C9 1.449(2) . ?
N2 C19 1.399(2) . ?
N2 C27 1.444(2) . ?
C00Y C33 1.539(2) . ?
C00Y C34 1.537(3) . ?
C00Y C35 1.542(3) . ?
C00Y C36 1.537(3) . ?
C1 C2 1.487(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.399(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.394(2) . ?
C6 C7 1.377(2) . ?
C9 C10 1.407(2) . ?
C9 C14 1.386(2) . ?
C10 C11 1.399(2) . ?
C10 C15 1.542(2) . ?
C11 C12 1.382(3) . ?
C12 C13 1.380(3) . ?
C13 C14 1.380(3) . ?
C15 C16 1.534(2) . ?
C15 C17 1.534(2) . ?
C15 C18 1.541(2) . ?
C19 C20 1.485(2) . ?
C20 C21 1.389(2) . ?
C20 C25 1.402(2) . ?
C21 C22 1.383(2) . ?
C22 C23 1.391(2) . ?
C23 C24 1.400(2) . ?
C24 C25 1.373(2) . ?
C27 C32 1.394(2) . ?
C27 C33 1.401(2) . ?
C29 C30 1.389(3) . ?
C29 C33 1.407(3) . ?
C30 C31 1.383(3) . ?
C31 C32 1.375(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
C5 O2 C8 117.42(13) . . ?
C23 O4 C26 117.65(14) . . ?
C1 N1 Cl1 116.57(11) . . ?
C1 N1 C9 119.15(13) . . ?
C9 N1 Cl1 112.22(10) . . ?
C19 N2 Cl2 116.81(11) . . ?
C19 N2 C27 117.57(13) . . ?
C27 N2 Cl2 112.34(10) . . ?
C33 C00Y C35 111.05(14) . . ?
C34 C00Y C33 111.70(16) . . ?
C34 C00Y C35 106.70(16) . . ?
C34 C00Y C36 107.54(16) . . ?
C36 C00Y C33 109.57(15) . . ?
C36 C00Y C35 110.18(16) . . ?
O1 C1 N1 119.51(15) . . ?
O1 C1 C2 122.93(15) . . ?
N1 C1 C2 117.34(14) . . ?
C3 C2 C1 122.90(15) . . ?
C3 C2 C7 118.92(15) . . ?
C7 C2 C1 118.05(15) . . ?
C2 C3 C4 121.24(15) . . ?
C5 C4 C3 118.98(15) . . ?
O2 C5 C4 124.84(15) . . ?
O2 C5 C6 115.01(14) . . ?
C4 C5 C6 120.15(15) . . ?
C7 C6 C5 120.54(15) . . ?
C6 C7 C2 120.13(15) . . ?
C10 C9 N1 120.43(15) . . ?
C14 C9 N1 117.12(15) . . ?
C14 C9 C10 122.43(15) . . ?
C9 C10 C15 124.11(15) . . ?
C11 C10 C9 114.88(16) . . ?
C11 C10 C15 121.01(15) . . ?
C12 C11 C10 122.95(17) . . ?
C13 C12 C11 120.56(17) . . ?
C14 C13 C12 118.49(17) . . ?
C13 C14 C9 120.67(17) . . ?
C16 C15 C10 111.42(15) . . ?
C16 C15 C17 107.10(14) . . ?
C16 C15 C18 107.36(14) . . ?
C17 C15 C10 111.89(14) . . ?
C17 C15 C18 109.21(15) . . ?
C18 C15 C10 109.73(14) . . ?
O3 C19 N2 118.50(15) . . ?
O3 C19 C20 121.92(15) . . ?
N2 C19 C20 119.32(14) . . ?
C21 C20 C19 124.27(15) . . ?
C21 C20 C25 118.49(16) . . ?
C25 C20 C19 116.90(15) . . ?
C22 C21 C20 121.73(16) . . ?
C21 C22 C23 119.01(16) . . ?
O4 C23 C22 125.29(16) . . ?
O4 C23 C24 114.63(15) . . ?
C22 C23 C24 120.07(16) . . ?
C25 C24 C23 120.02(15) . . ?
C24 C25 C20 120.63(16) . . ?
C32 C27 N2 116.62(15) . . ?
C32 C27 C33 122.42(16) . . ?
C33 C27 N2 120.96(15) . . ?
C30 C29 C33 122.30(18) . . ?
C31 C30 C29 120.69(18) . . ?
C32 C31 C30 118.64(18) . . ?
C31 C32 C27 120.67(18) . . ?
C27 C33 C00Y 123.86(15) . . ?
C27 C33 C29 115.28(17) . . ?
C29 C33 C00Y 120.85(16) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_rja230010_fa
_database_code_depnum_ccdc_archive 'CCDC 2307640'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.5-ac5-023
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 Cl F2.998 N O'
_chemical_formula_sum            'C18 H17 Cl F3 N O'
_chemical_formula_weight         355.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 Cl1 F3 N1 O1'
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'
F F 0.0727 0.0534 '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                   6.21560(10)
_cell_length_b                   11.1571(3)
_cell_length_c                   24.7517(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.551(2)
_cell_angle_gamma                90
_cell_volume                     1714.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.9080
_cell_measurement_theta_min      3.5570
_shelx_estimated_absorpt_T_max   0.914
_shelx_estimated_absorpt_T_min   0.620
_exptl_absorpt_coefficient_mu    2.295
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.0230
0 1 0 0.0210
0 0 -1 0.0225
0 0 1 0.0225
-1 0 1 0.0993
1 0 -1 0.1163

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
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
-0.0007 -1.0000 0.0001 -0.0806 0.1073 0.0325
0.0007 1.0000 -0.0001 0.0806 -0.1073 -0.0325
0.0002 -0.0000 -1.0004 0.0484 0.0386 -0.0073
-0.0002 0.0000 1.0004 -0.0484 -0.0386 0.0073
-0.9998 -0.0004 0.9988 0.0186 -0.0599 0.2452
0.9998 0.0004 -0.9988 -0.0186 0.0599 -0.2452

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18811
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.919
_diffrn_reflns_theta_min         3.575
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  28.00   0.50    0.37    --  -49.76  19.00 120.00  108
  2  ω    -22.00  29.00   0.50    0.37    --  -49.76  19.00   0.00  102
  3  ω   -105.00 -45.00   0.50    0.37    --  -92.01  77.00 -30.00  120
  4  ω    -71.00 -17.00   0.50    0.37    --  -92.01  61.00-150.00  108
  5  ω    -51.00 -26.00   0.50    0.37    --  -92.01  45.00-180.00   50
  6  ω    -26.00  23.00   0.50    0.37    --  -49.76  19.00-150.00   98
  7  ω    -24.00  28.00   0.50    0.37    --  -49.76  19.00 -60.00  104
  8  ω   -108.00 -66.00   0.50    0.37    --  -92.01 109.00  -4.00   84
  9  ω   -110.00 -20.00   0.50    0.37    --  -92.01 125.00  30.00  180
 10  ω    -31.00  -1.00   0.50    0.37    --  -49.76 109.00  -4.00   60
 11  ω   -118.00 -37.00   0.50    0.37    --  -99.00 133.00 151.67  162
 12  ω   -171.00 -79.00   0.50    0.37    --  -92.01 -30.00  90.00  184
 13  ω   -103.00 -65.00   0.50    0.37    --  -92.01 -77.00 -60.00   76
 14  ω    -93.00 -68.00   0.50    0.37    --  -94.00 -75.00 -52.10   50
 15  ω   -104.00 -65.00   0.50    0.37    --  -92.01 -77.00-180.00   78
 16  ω   -160.00-122.00   0.50    0.37    --  -92.01 -77.00-180.00   76
 17  ω   -149.00 -82.00   0.50    0.37    --  -92.01-109.00-100.00  134
 18  ω   -122.00 -81.00   0.50    0.37    --  -49.76-125.00 -30.00   82
 19  ω     44.00  69.00   0.50    0.37    --  108.00 -77.00 -90.00   50
 20  ω     71.00  97.00   0.50    0.37    --  108.00 -77.00 -90.00   52
 21  ω     47.00 100.00   0.50    0.37    --  108.00 -77.00   0.00  106
 22  ω     41.00  91.00   0.50    0.37    --  108.00 -77.00  90.00  100
 23  ω     22.00  48.00   0.50    0.37    --   96.11 -45.00 120.00   52
 24  ω     20.00  51.00   0.50    0.37    --   96.11 -45.00  90.00   62
 25  ω     19.00  44.00   0.50    0.37    --   96.11 -45.00  30.00   50
 26  ω     19.00  50.00   0.50    0.37    --   96.11 -45.00 -30.00   62
 27  ω     19.00  51.00   0.50    0.37    --   96.11 -45.00 -90.00   64
 28  ω     25.00  50.00   0.50    0.37    --   96.11 -45.00-120.00   50
 29  ω     -8.00  25.00   0.50    0.37    --   48.76 -19.00 -90.00   66
 30  ω      1.00  69.00   0.50    0.37    --   48.76-109.00-100.00  136
 31  ω     79.00 106.00   0.50    0.37    --   96.11-109.00-100.00   54
 32  ω     49.00  74.00   0.50    0.37    --  108.00-109.00-100.00   50
 33  ω     37.00  71.00   0.50    0.37    --   96.11-109.00-100.00   68
 34  ω    136.00 177.00   0.50    0.37    --  108.00  45.00 150.00   82
 35  ω    101.00 126.00   0.50    0.37    --   96.11 109.00  -4.00   50
 36  ω     88.00 113.00   0.50    0.37    --  108.00 109.00  -4.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0669536000
_diffrn_orient_matrix_UB_12      0.0806550000
_diffrn_orient_matrix_UB_13      -0.0483839000
_diffrn_orient_matrix_UB_21      0.0214130000
_diffrn_orient_matrix_UB_22      -0.1073038000
_diffrn_orient_matrix_UB_23      -0.0385430000
_diffrn_orient_matrix_UB_31      -0.2380109000
_diffrn_orient_matrix_UB_32      -0.0323477000
_diffrn_orient_matrix_UB_33      0.0072576000
_diffrn_oxdiff_digest_frames     
;
01d3d39685bfae4f1fb6df4b80f1963ad10306085ac
;
_diffrn_oxdiff_digest_hkl        
;
01cfcc104836c0b903f9c8f773220fe9051da0
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3099
_reflns_number_total             3491
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-023 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     420
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.112
_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)+(0.0471P)²+0.6771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          
;
The fluorine atoms in the trifluoromethyl group in this 
structure have been modelled as disordered over three 
positions. The occupancies of the three sites were refined 
independently of the atomic displacement parameters. The 
carbon-fluorine bonds were restrained to be similar using 
the SADI card and the atomic displacement parameters for 
the partially-occupied fluorine atoms were restrained to be 
similar using the SIMU card.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F1C-C8 \\sim F1B-C8 \\sim F1A-C8 \\sim F3C-C8 \\sim F3A-C8 \\sim F3B-C8 \\sim
F2C-C8 \\sim F2B-C8 \\sim F2A-C8
 with sigma of 0.02
 F1A-F2A \\sim F1A-F3A \\sim F2A-F3A \\sim F1B-F2B \\sim F1B-F3B \\sim F2B-F3B
\\sim F1C-F2C \\sim F1C-F3C
 \\sim F2C-F3C
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F1A \\sim F2A \\sim F3A \\sim F1B \\sim F2B \\sim F3B \\sim F1C \\sim F2C \\sim
F3C: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: F1A(0.37372) F2A(0.37372) F3A(0.37372) F1B(0.49655) F2B(0.49655)
 F3B(0.49655) F1C(0.12892) F2C(0.12892) F3C(0.12892)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14)
6.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.53532(7) 0.48025(4) 0.77490(2) 0.04260(15) Uani 1 1 d . . . . .
O1 O 1.03431(17) 0.63697(11) 0.73055(4) 0.0347(3) Uani 1 1 d . . . . .
N1 N 0.75641(19) 0.57406(11) 0.77881(5) 0.0265(3) Uani 1 1 d . . . . .
C1 C 0.8464(2) 0.60806(13) 0.73089(6) 0.0263(3) Uani 1 1 d . . . . .
C2 C 0.6990(2) 0.62098(13) 0.68173(6) 0.0256(3) Uani 1 1 d . . . . .
C3 C 0.7804(2) 0.59135(14) 0.63164(6) 0.0288(3) Uani 1 1 d . . . . .
H3 H 0.919268 0.556252 0.630023 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6590(2) 0.61311(14) 0.58453(6) 0.0296(3) Uani 1 1 d . . . . .
H4 H 0.712705 0.591388 0.550546 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4582(2) 0.66688(14) 0.58709(6) 0.0288(3) Uani 1 1 d . . . . .
C6 C 0.3769(2) 0.69743(14) 0.63662(6) 0.0295(3) Uani 1 1 d . . . . .
H6 H 0.239897 0.734713 0.638087 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4970(2) 0.67319(14) 0.68391(6) 0.0281(3) Uani 1 1 d . . . . .
H7 H 0.440752 0.692391 0.717909 0.034 Uiso 1 1 calc R U . . .
C8 C 0.3319(3) 0.69768(17) 0.53622(7) 0.0385(4) Uani 1 1 d D . . . .
C9 C 0.8912(2) 0.55574(14) 0.82732(6) 0.0261(3) Uani 1 1 d . . . . .
C10 C 0.8955(2) 0.64008(14) 0.86932(6) 0.0278(3) Uani 1 1 d . . . . .
C11 C 1.0229(3) 0.60812(15) 0.91532(7) 0.0348(4) Uani 1 1 d . . . . .
H11 H 1.029935 0.661490 0.945247 0.042 Uiso 1 1 calc R U . . .
C12 C 1.1390(3) 0.50220(16) 0.91900(7) 0.0392(4) Uani 1 1 d . . . . .
H12 H 1.222700 0.484281 0.951022 0.047 Uiso 1 1 calc R U . . .
C13 C 1.1332(3) 0.42262(15) 0.87626(7) 0.0377(4) Uani 1 1 d . . . . .
H13 H 1.214327 0.350476 0.878323 0.045 Uiso 1 1 calc R U . . .
C14 C 1.0074(3) 0.44962(15) 0.83043(7) 0.0324(3) Uani 1 1 d . . . . .
H14 H 1.000560 0.395208 0.800877 0.039 Uiso 1 1 calc R U . . .
C15 C 0.7745(3) 0.76046(14) 0.86692(6) 0.0316(3) Uani 1 1 d . . . . .
C16 C 0.8480(3) 0.83618(15) 0.81911(7) 0.0365(4) Uani 1 1 d . . . . .
H16A H 1.005691 0.839871 0.820159 0.055 Uiso 1 1 calc R U . . .
H16B H 0.789461 0.917426 0.821693 0.055 Uiso 1 1 calc R U . . .
H16C H 0.795752 0.799425 0.785039 0.055 Uiso 1 1 calc R U . . .
C17 C 0.5296(3) 0.74081(18) 0.86172(8) 0.0451(4) Uani 1 1 d . . . . .
H17A H 0.492542 0.699476 0.827633 0.068 Uiso 1 1 calc R U . . .
H17B H 0.456114 0.818488 0.862139 0.068 Uiso 1 1 calc R U . . .
H17C H 0.484161 0.691947 0.892072 0.068 Uiso 1 1 calc R U . . .
C18 C 0.8226(3) 0.83466(17) 0.91836(7) 0.0444(4) Uani 1 1 d . . . . .
H18A H 0.777146 0.789822 0.949933 0.067 Uiso 1 1 calc R U . . .
H18B H 0.743818 0.910670 0.915752 0.067 Uiso 1 1 calc R U . . .
H18C H 0.977508 0.850785 0.922195 0.067 Uiso 1 1 calc R U . . .
F1A F 0.334(2) 0.6088(9) 0.5009(5) 0.059(3) Uani 0.3737 1 d D U P A 1
F2A F 0.4241(18) 0.7926(7) 0.5112(5) 0.0512(19) Uani 0.3737 1 d D U P A 1
F3A F 0.1300(14) 0.7317(9) 0.5429(6) 0.051(2) Uani 0.3737 1 d D U P A 1
F1B F 0.3771(15) 0.6279(7) 0.4941(4) 0.0448(13) Uani 0.4965 1 d D U P A 2
F2B F 0.3729(13) 0.8102(5) 0.5202(4) 0.0552(16) Uani 0.4965 1 d D U P A 2
F3B F 0.1220(10) 0.6907(7) 0.5418(5) 0.0540(19) Uani 0.4965 1 d D U P A 2
F1C F 0.421(2) 0.6824(14) 0.4910(5) 0.062(4) Uani 0.1289 1 d D U P A 3
F2C F 0.228(3) 0.7994(11) 0.5367(5) 0.080(4) Uani 0.1289 1 d D U P A 3
F3C F 0.1573(19) 0.6128(13) 0.5326(5) 0.068(3) Uani 0.1289 1 d D U P A 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
Cl1 N1 1.7267(13) . ?
O1 C1 1.2123(18) . ?
N1 C1 1.3865(19) . ?
N1 C9 1.4478(18) . ?
C1 C2 1.497(2) . ?
C2 C3 1.400(2) . ?
C2 C7 1.387(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.389(2) . ?
C5 C6 1.389(2) . ?
C5 C8 1.494(2) . ?
C6 C7 1.386(2) . ?
C8 F1A 1.322(8) . ?
C8 F2A 1.365(8) . ?
C8 F3A 1.328(8) . ?
C8 F1B 1.342(6) . ?
C8 F2B 1.345(6) . ?
C8 F3B 1.320(6) . ?
C8 F1C 1.281(9) . ?
C8 F2C 1.306(9) . ?
C8 F3C 1.440(9) . ?
C9 C10 1.402(2) . ?
C9 C14 1.387(2) . ?
C10 C11 1.404(2) . ?
C10 C15 1.539(2) . ?
C11 C12 1.385(2) . ?
C12 C13 1.380(3) . ?
C13 C14 1.382(2) . ?
C15 C16 1.540(2) . ?
C15 C17 1.537(2) . ?
C15 C18 1.537(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
C1 N1 Cl1 117.92(10) . . ?
C1 N1 C9 120.50(12) . . ?
C9 N1 Cl1 112.99(9) . . ?
O1 C1 N1 120.28(13) . . ?
O1 C1 C2 121.58(13) . . ?
N1 C1 C2 117.78(12) . . ?
C3 C2 C1 117.70(13) . . ?
C7 C2 C1 122.07(13) . . ?
C7 C2 C3 119.83(14) . . ?
C4 C3 C2 120.03(14) . . ?
C3 C4 C5 119.71(13) . . ?
C4 C5 C6 120.61(14) . . ?
C4 C5 C8 120.05(14) . . ?
C6 C5 C8 119.28(14) . . ?
C7 C6 C5 119.60(14) . . ?
C6 C7 C2 120.21(14) . . ?
F1A C8 C5 111.3(7) . . ?
F1A C8 F2A 105.4(6) . . ?
F1A C8 F3A 109.5(8) . . ?
F2A C8 C5 110.2(7) . . ?
F3A C8 C5 115.2(7) . . ?
F3A C8 F2A 104.6(6) . . ?
F1B C8 C5 113.7(5) . . ?
F1B C8 F2B 105.3(5) . . ?
F2B C8 C5 111.4(5) . . ?
F3B C8 C5 112.6(5) . . ?
F3B C8 F1B 106.8(6) . . ?
F3B C8 F2B 106.7(5) . . ?
F1C C8 C5 118.3(7) . . ?
F1C C8 F2C 110.9(8) . . ?
F1C C8 F3C 102.2(7) . . ?
F2C C8 C5 115.7(6) . . ?
F2C C8 F3C 101.5(8) . . ?
F3C C8 C5 105.5(5) . . ?
C10 C9 N1 120.77(13) . . ?
C14 C9 N1 116.56(14) . . ?
C14 C9 C10 122.63(14) . . ?
C9 C10 C11 114.99(14) . . ?
C9 C10 C15 124.33(13) . . ?
C11 C10 C15 120.67(14) . . ?
C12 C11 C10 122.91(16) . . ?
C13 C12 C11 120.18(15) . . ?
C12 C13 C14 118.91(15) . . ?
C13 C14 C9 120.37(15) . . ?
C10 C15 C16 110.30(13) . . ?
C17 C15 C10 111.04(14) . . ?
C17 C15 C16 109.91(14) . . ?
C18 C15 C10 111.18(13) . . ?
C18 C15 C16 106.72(14) . . ?
C18 C15 C17 107.56(14) . . ?

_shelx_SHELXL_version_number     2019/1
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.624
####################################################################### 
# 
# 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_rja230007_fa
_database_code_depnum_ccdc_archive 'CCDC 2307642'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H24 Cl N O'
_chemical_formula_sum            'C17 H24 Cl N O'
_chemical_formula_weight         293.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H24 Cl1 N1 O1'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.22350(10)
_cell_length_b                   7.00790(10)
_cell_length_c                   25.1221(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.528(2)
_cell_angle_gamma                90
_cell_volume                     1618.76(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9289
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.5450
_cell_measurement_theta_min      3.5210
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.822
_exptl_absorpt_coefficient_mu    2.041
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.0134
-1 0 1 0.0134
0 1 0 0.0417
0 -1 0 0.0417
0 0 1 0.0382
0 0 -1 0.0532

_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
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
1.0000 0.0000 -1.0000 -0.1693 0.0203 -0.0338
-1.0000 -0.0000 1.0000 0.1693 -0.0203 0.0338
0.0000 1.0000 -0.0000 0.0459 0.1752 -0.1246
-0.0000 -1.0000 0.0000 -0.0459 -0.1752 0.1246
0.0000 -0.0000 1.0000 0.0219 -0.0370 -0.0440
-0.0000 0.0000 -1.0000 -0.0219 0.0370 0.0440

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            15611
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.336
_diffrn_reflns_theta_min         3.530
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -161.00 -66.00   0.50    0.57    --  -92.01 -75.00  11.00  190
  2  ω    -71.00 -17.00   0.50    0.57    --  -92.01  61.00 -30.00  108
  3  ω    -51.00 -14.00   0.50    0.57    --  -92.01  45.00 120.00   74
  4  ω    -98.00 -23.00   0.50    0.57    --  -92.01  75.00 139.00  150
  5  ω    -75.00  20.00   0.50    0.57    --  -49.76  75.00 139.00  190
  6  ω     22.00  96.00   0.50    0.57    --   48.76  77.00  30.00  148
  7  ω     29.00 124.00   0.50    0.57    --   48.76  57.00 -90.00  190
  8  ω     23.00 118.00   0.50    0.57    --   48.76  75.00 139.00  190
  9  ω     75.00 176.00   0.50    0.57    --   96.11  30.00  90.00  202
 10  ω     82.00 177.00   0.50    0.57    --  108.00  75.00 139.00  190
 11  ω     71.00 165.00   0.50    0.57    --   96.11  75.00 139.00  188
 12  ω     74.00 121.00   0.50    0.57    --   48.76 125.00  60.00   94
 13  ω     34.00  71.00   0.50    0.57    --  108.00 -61.00  60.00   74
 14  ω     39.00  98.00   0.50    0.57    --  108.00 -75.00  11.00  118
 15  ω     27.00  98.00   0.50    0.57    --   96.11 -75.00  11.00  142
 16  ω     40.00 105.00   0.50    0.57    --  108.00 -77.00-150.00  130
 17  ω     18.00  51.00   0.50    0.57    --   96.11 -45.00-180.00   66
 18  ω     18.00  51.00   0.50    0.57    --   96.11 -45.00-150.00   66
 19  ω     18.00  51.00   0.50    0.57    --   96.11 -45.00   0.00   66
 20  ω    -20.00  75.00   0.50    0.57    --   48.76 -75.00  11.00  190
 21  ω     34.00  71.00   0.50    0.57    --  108.00 -61.00 150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1474226000
_diffrn_orient_matrix_UB_12      0.0459158000
_diffrn_orient_matrix_UB_13      0.0218874000
_diffrn_orient_matrix_UB_21      -0.0166958000
_diffrn_orient_matrix_UB_22      0.1751677000
_diffrn_orient_matrix_UB_23      -0.0370281000
_diffrn_orient_matrix_UB_31      -0.0777858000
_diffrn_orient_matrix_UB_32      -0.1246062000
_diffrn_orient_matrix_UB_33      -0.0439977000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2836
_reflns_number_total             3262
_reflns_odcompleteness_completeness 99.97
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.517
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.044
_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)+(0.0518P)²+0.5182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1014
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.37978(4) 1.08840(6) 0.27942(2) 0.03562(13) Uani 1 1 d . . . . .
O1 O 0.15912(11) 0.88698(17) 0.32519(5) 0.0394(3) Uani 1 1 d . . . . .
N1 N 0.40644(13) 0.91080(18) 0.32752(4) 0.0277(3) Uani 1 1 d . . . . .
C1 C 0.27778(15) 0.8262(2) 0.34131(6) 0.0291(3) Uani 1 1 d . . . . .
C2 C 0.29564(15) 0.6636(2) 0.38128(6) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.401603 0.639052 0.390145 0.036 Uiso 1 1 calc R U . . .
C3 C 0.22524(17) 0.7206(3) 0.43228(6) 0.0366(4) Uani 1 1 d . . . . .
H3A H 0.276616 0.832890 0.448563 0.044 Uiso 1 1 calc R U . . .
H3B H 0.122634 0.757129 0.423059 0.044 Uiso 1 1 calc R U . . .
C4 C 0.2310(2) 0.5576(3) 0.47245(7) 0.0481(4) Uani 1 1 d . . . . .
H4A H 0.333693 0.529288 0.484275 0.058 Uiso 1 1 calc R U . . .
H4B H 0.181008 0.596617 0.504156 0.058 Uiso 1 1 calc R U . . .
C5 C 0.1591(2) 0.3794(3) 0.44827(7) 0.0505(5) Uani 1 1 d . . . . .
H5A H 0.054202 0.403915 0.439593 0.061 Uiso 1 1 calc R U . . .
H5B H 0.168630 0.274031 0.474571 0.061 Uiso 1 1 calc R U . . .
C6 C 0.2290(2) 0.3208(3) 0.39778(7) 0.0476(4) Uani 1 1 d . . . . .
H6A H 0.331446 0.283902 0.407115 0.057 Uiso 1 1 calc R U . . .
H6B H 0.177256 0.208496 0.381705 0.057 Uiso 1 1 calc R U . . .
C7 C 0.22389(18) 0.4827(2) 0.35731(6) 0.0367(4) Uani 1 1 d . . . . .
H7A H 0.121353 0.510455 0.345140 0.044 Uiso 1 1 calc R U . . .
H7B H 0.274570 0.442759 0.325842 0.044 Uiso 1 1 calc R U . . .
C8 C 0.53391(15) 0.7960(2) 0.31901(5) 0.0275(3) Uani 1 1 d . . . . .
C9 C 0.66795(15) 0.8236(2) 0.34872(5) 0.0282(3) Uani 1 1 d . . . . .
C10 C 0.78042(16) 0.7039(2) 0.33448(6) 0.0354(3) Uani 1 1 d . . . . .
H10 H 0.873342 0.715899 0.353362 0.042 Uiso 1 1 calc R U . . .
C11 C 0.76263(19) 0.5694(2) 0.29435(7) 0.0414(4) Uani 1 1 d . . . . .
H11 H 0.842692 0.492563 0.286076 0.050 Uiso 1 1 calc R U . . .
C12 C 0.62910(19) 0.5458(2) 0.26615(7) 0.0411(4) Uani 1 1 d . . . . .
H12 H 0.616070 0.452469 0.238769 0.049 Uiso 1 1 calc R U . . .
C13 C 0.51512(17) 0.6606(2) 0.27855(6) 0.0338(3) Uani 1 1 d . . . . .
H13 H 0.422843 0.647069 0.259286 0.041 Uiso 1 1 calc R U . . .
C14 C 0.69546(15) 0.9744(2) 0.39298(6) 0.0313(3) Uani 1 1 d . . . . .
C15 C 0.85193(17) 0.9611(3) 0.41905(7) 0.0454(4) Uani 1 1 d . . . . .
H15A H 0.869064 0.832712 0.433707 0.068 Uiso 1 1 calc R U . . .
H15B H 0.865418 1.055233 0.447855 0.068 Uiso 1 1 calc R U . . .
H15C H 0.920879 0.986771 0.392181 0.068 Uiso 1 1 calc R U . . .
C16 C 0.59324(18) 0.9452(3) 0.43763(6) 0.0415(4) Uani 1 1 d . . . . .
H16A H 0.492427 0.965269 0.423357 0.062 Uiso 1 1 calc R U . . .
H16B H 0.617772 1.036652 0.466446 0.062 Uiso 1 1 calc R U . . .
H16C H 0.604262 0.814963 0.451590 0.062 Uiso 1 1 calc R U . . .
C17 C 0.6757(2) 1.1750(2) 0.36980(7) 0.0444(4) Uani 1 1 d . . . . .
H17A H 0.738090 1.190828 0.340289 0.067 Uiso 1 1 calc R U . . .
H17B H 0.702507 1.269363 0.397639 0.067 Uiso 1 1 calc R U . . .
H17C H 0.573844 1.193502 0.356592 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7386(12) . ?
O1 C1 1.2138(17) . ?
N1 C1 1.3946(19) . ?
N1 C8 1.4540(18) . ?
C1 C2 1.519(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.5343(19) . ?
C2 C7 1.531(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.518(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.524(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.406(2) . ?
C8 C13 1.392(2) . ?
C9 C10 1.402(2) . ?
C9 C14 1.540(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.381(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.540(2) . ?
C14 C16 1.535(2) . ?
C14 C17 1.527(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 N1 Cl1 113.61(9) . . ?
C1 N1 C8 121.01(12) . . ?
C8 N1 Cl1 111.44(9) . . ?
O1 C1 N1 122.04(14) . . ?
O1 C1 C2 122.12(13) . . ?
N1 C1 C2 115.67(12) . . ?
C1 C2 H2 109.2 . . ?
C1 C2 C3 109.01(12) . . ?
C1 C2 C7 109.88(12) . . ?
C3 C2 H2 109.2 . . ?
C7 C2 H2 109.2 . . ?
C7 C2 C3 110.22(12) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.29(14) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.15(14) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.75(15) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.27(15) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C2 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 C2 111.40(13) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 N1 122.23(13) . . ?
C13 C8 N1 115.40(12) . . ?
C13 C8 C9 122.35(13) . . ?
C8 C9 C14 124.42(13) . . ?
C10 C9 C8 114.80(14) . . ?
C10 C9 C14 120.77(13) . . ?
C9 C10 H10 118.4 . . ?
C11 C10 C9 123.18(15) . . ?
C11 C10 H10 118.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.39(15) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.7 . . ?
C13 C12 C11 118.64(15) . . ?
C13 C12 H12 120.7 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.65(15) . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C9 111.15(13) . . ?
C16 C14 C9 111.13(12) . . ?
C16 C14 C15 106.88(12) . . ?
C17 C14 C9 110.38(12) . . ?
C17 C14 C15 107.31(14) . . ?
C17 C14 C16 109.86(14) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
Cl1 N1 C1 O1 -7.56(18) . . . . ?
Cl1 N1 C1 C2 177.22(9) . . . . ?
Cl1 N1 C8 C9 100.67(13) . . . . ?
Cl1 N1 C8 C13 -77.72(14) . . . . ?
O1 C1 C2 C3 -58.71(18) . . . . ?
O1 C1 C2 C7 62.18(18) . . . . ?
N1 C1 C2 C3 116.50(14) . . . . ?
N1 C1 C2 C7 -122.61(13) . . . . ?
N1 C8 C9 C10 -178.47(12) . . . . ?
N1 C8 C9 C14 0.3(2) . . . . ?
N1 C8 C13 C12 178.78(13) . . . . ?
C1 N1 C8 C9 -121.75(15) . . . . ?
C1 N1 C8 C13 59.85(17) . . . . ?
C1 C2 C3 C4 176.22(13) . . . . ?
C1 C2 C7 C6 -175.47(13) . . . . ?
C2 C3 C4 C5 -56.55(19) . . . . ?
C3 C2 C7 C6 -55.31(17) . . . . ?
C3 C4 C5 C6 56.4(2) . . . . ?
C4 C5 C6 C7 -56.2(2) . . . . ?
C5 C6 C7 C2 56.0(2) . . . . ?
C7 C2 C3 C4 55.54(17) . . . . ?
C8 N1 C1 O1 -144.30(14) . . . . ?
C8 N1 C1 C2 40.48(17) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C8 C9 C14 C15 177.64(14) . . . . ?
C8 C9 C14 C16 58.74(19) . . . . ?
C8 C9 C14 C17 -63.41(18) . . . . ?
C9 C8 C13 C12 0.4(2) . . . . ?
C9 C10 C11 C12 -0.6(2) . . . . ?
C10 C9 C14 C15 -3.69(19) . . . . ?
C10 C9 C14 C16 -122.59(15) . . . . ?
C10 C9 C14 C17 115.26(15) . . . . ?
C10 C11 C12 C13 0.7(2) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
C13 C8 C9 C14 178.55(13) . . . . ?
C14 C9 C10 C11 -178.52(14) . . . . ?

_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 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.598
####################################################################### 
# 
# 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_rja230003_fa
_database_code_depnum_ccdc_archive 'CCDC 2307644'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H18 Cl N O'
_chemical_formula_sum            'C14 H18 Cl N O'
_chemical_formula_weight         251.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H18 Cl1 N1 O1'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.5653(4)
_cell_length_b                   6.36990(10)
_cell_length_c                   23.6434(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.817(2)
_cell_angle_gamma                90
_cell_volume                     2646.61(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6863
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.1680
_cell_measurement_theta_min      3.9400
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.562
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  0.931
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0339
0 0 1 0.0529
0 1 1 0.1354
0 -1 -1 0.1014
-1 0 0 0.0206
1 0 0 0.0106

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
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
-0.0000 0.0000 -1.0000 0.0431 0.0428 -0.0324
0.0000 -0.0000 1.0000 -0.0431 -0.0428 0.0324
-0.0000 1.0000 1.0000 0.0395 0.0355 0.2458
0.0000 -1.0000 -1.0000 -0.0395 -0.0355 -0.2458
-1.0000 0.0000 0.0000 -0.0405 0.0767 -0.0125
1.0000 -0.0000 -0.0000 0.0405 -0.0767 0.0125

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            14323
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.563
_diffrn_reflns_theta_min         3.950
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00 -15.00   0.50    0.15    --  -92.01  45.00 120.00   50
  2  ω    -45.00 -19.00   0.50    0.15    --  -92.01  45.00  90.00   52
  3  ω    -65.00 -17.00   0.50    0.15    --  -92.01  61.00  30.00   96
  4  ω    -41.00 -14.00   0.50    0.15    --  -92.01  37.00 -58.00   54
  5  ω    -70.00 -17.00   0.50    0.15    --  -92.01  61.00-120.00  106
  6  ω    -31.00  -6.00   0.50    0.15    --  -49.76  37.00 -58.00   50
  7  ω    -25.00  13.00   0.50    0.15    --  -49.76  19.00 -90.00   76
  8  ω    -24.00  28.00   0.50    0.15    --  -49.76  19.00 -60.00  104
  9  ω    -23.00   5.00   0.50    0.15    --   48.76 -37.00 146.00   56
 10  ω     17.00  42.00   0.50    0.15    --   50.00  89.00 141.14   50
 11  ω     75.00 121.00   0.50    0.15    --   48.76 125.00-180.00   92
 12  ω    110.00 135.00   0.50    0.15    --  108.00  37.00 -58.00   50
 13  ω     72.00 150.00   0.50    0.15    --   96.11  77.00   0.00  156
 14  ω     79.00 155.00   0.50    0.15    --   96.11  77.00  30.00  152
 15  ω     87.00 165.00   0.50    0.15    --   96.11  77.00  90.00  156
 16  ω     71.00 110.00   0.50    0.15    --   96.11  77.00  60.00   78
 17  ω     50.00  85.00   0.50    0.15    --   48.76  37.00 -58.00   70
 18  ω     88.00 119.00   0.50    0.15    --   48.76  37.00 -58.00   62
 19  ω    120.00 145.00   0.50    0.15    --   96.11  37.00 -58.00   50
 20  ω     47.00  73.00   0.50    0.15    --  108.00 -77.00-180.00   52
 21  ω     34.00  70.00   0.50    0.15    --  108.00 -61.00 -90.00   72
 22  ω     46.00  71.00   0.50    0.15    --  108.00 -61.00   0.00   50
 23  ω     47.00  80.00   0.50    0.15    --  108.00 -77.00  60.00   66
 24  ω     40.00  89.00   0.50    0.15    --  108.00 -77.00 120.00   98
 25  ω    -81.00 -52.00   0.50    0.15    --  -49.76 -37.00 146.00   58
 26  ω    -90.00 -23.00   0.50    0.15    --  -49.76 -77.00  60.00  134
 27  ω    -45.00 -19.00   0.50    0.15    --  -92.01 125.00-150.00   52
 28  ω   -108.00 -54.00   0.50    0.15    --  -92.01 125.00-150.00  108
 29  ω    -91.00 -66.00   0.50    0.15    --  -92.01 -77.00  90.00   50
 30  ω    -89.00 -64.00   0.50    0.15    --  -86.00 -66.00  45.02   50
 31  ω    -99.00 -73.00   0.50    0.15    --  -92.01 -77.00  30.00   52
 32  ω    -86.00 -60.00   0.50    0.15    --  -82.00 -66.00  27.60   52
 33  ω   -156.00 -68.00   0.50    0.15    --  -92.01 -77.00   0.00  176
 34  ω   -148.00-123.00   0.50    0.15    --  -92.01 -77.00  30.00   50
 35  ω   -151.00 -60.00   0.50    0.15    --  -78.00 -61.00   0.81  182
 36  ω   -146.00 -75.00   0.50    0.15    --  -92.01 -45.00  60.00  142
 37  ω   -114.00 -75.00   0.50    0.15    --  -92.01 -37.00 146.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0404899000
_diffrn_orient_matrix_UB_12      0.0826326000
_diffrn_orient_matrix_UB_13      -0.0430851000
_diffrn_orient_matrix_UB_21      -0.0767443000
_diffrn_orient_matrix_UB_22      0.0783422000
_diffrn_orient_matrix_UB_23      -0.0427992000
_diffrn_orient_matrix_UB_31      0.0125212000
_diffrn_orient_matrix_UB_32      0.2134054000
_diffrn_orient_matrix_UB_33      0.0323809000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2344
_reflns_number_total             2651
_reflns_odcompleteness_completeness 100.00
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.651
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0607
_refine_ls_restrained_S_all      1.051
_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)+(0.0702P)²+7.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1619
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45200(4) 0.28841(11) 0.32537(4) 0.0526(3) Uani 1 1 d . . . . .
O1 O 0.59911(12) 0.4488(3) 0.37760(12) 0.0556(6) Uani 1 1 d . . . . .
N1 N 0.47459(12) 0.5346(3) 0.35726(11) 0.0380(5) Uani 1 1 d . . . . .
C1 C 0.55173(15) 0.5826(4) 0.37450(13) 0.0389(6) Uani 1 1 d . . . . .
C2 C 0.57040(15) 0.8058(4) 0.38956(12) 0.0360(6) Uani 1 1 d . . . . .
H2 H 0.529542 0.897046 0.395413 0.043 Uiso 1 1 calc R U . . .
C3 C 0.65152(16) 0.8541(5) 0.42637(13) 0.0433(7) Uani 1 1 d . . . . .
H3A H 0.660352 0.972133 0.455058 0.052 Uiso 1 1 calc R U . . .
H3B H 0.686939 0.734418 0.439799 0.052 Uiso 1 1 calc R U . . .
C4 C 0.62547(15) 0.9055(5) 0.36211(13) 0.0409(6) Uani 1 1 d . . . . .
H4A H 0.644528 0.817584 0.335443 0.049 Uiso 1 1 calc R U . . .
H4B H 0.617931 1.055382 0.350707 0.049 Uiso 1 1 calc R U . . .
C5 C 0.41471(15) 0.6850(4) 0.33158(11) 0.0334(6) Uani 1 1 d . . . . .
C6 C 0.36264(14) 0.7423(4) 0.36046(11) 0.0305(5) Uani 1 1 d . . . . .
C7 C 0.30617(16) 0.8848(4) 0.32940(13) 0.0411(6) Uani 1 1 d . . . . .
H7 H 0.269843 0.928754 0.347503 0.049 Uiso 1 1 calc R U . . .
C8 C 0.3006(2) 0.9647(5) 0.27386(14) 0.0541(8) Uani 1 1 d . . . . .
H8 H 0.260802 1.059536 0.254537 0.065 Uiso 1 1 calc R U . . .
C9 C 0.3523(2) 0.9075(5) 0.24670(14) 0.0589(10) Uani 1 1 d . . . . .
H9 H 0.348849 0.962645 0.208596 0.071 Uiso 1 1 calc R U . . .
C10 C 0.4096(2) 0.7683(5) 0.27528(13) 0.0502(8) Uani 1 1 d . . . . .
H10 H 0.445951 0.728473 0.256730 0.060 Uiso 1 1 calc R U . . .
C11 C 0.36500(13) 0.6621(4) 0.42235(11) 0.0308(5) Uani 1 1 d . . . . .
C12 C 0.29688(16) 0.7430(6) 0.43942(14) 0.0486(7) Uani 1 1 d . . . . .
H12A H 0.296823 0.896884 0.439166 0.073 Uiso 1 1 calc R U . . .
H12B H 0.300781 0.692601 0.479459 0.073 Uiso 1 1 calc R U . . .
H12C H 0.249542 0.691265 0.410527 0.073 Uiso 1 1 calc R U . . .
C13 C 0.36184(18) 0.4217(5) 0.42425(13) 0.0432(7) Uani 1 1 d . . . . .
H13A H 0.317147 0.371641 0.392136 0.065 Uiso 1 1 calc R U . . .
H13B H 0.358339 0.376844 0.462919 0.065 Uiso 1 1 calc R U . . .
H13C H 0.408023 0.363130 0.418898 0.065 Uiso 1 1 calc R U . . .
C14 C 0.43698(15) 0.7441(5) 0.47004(12) 0.0387(6) Uani 1 1 d . . . . .
H14A H 0.482024 0.681750 0.463692 0.058 Uiso 1 1 calc R U . . .
H14B H 0.435589 0.705557 0.509803 0.058 Uiso 1 1 calc R U . . .
H14C H 0.439274 0.897230 0.467065 0.058 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.732(2) . ?
O1 C1 1.210(3) . ?
N1 C1 1.391(3) . ?
N1 C5 1.445(4) . ?
C1 C2 1.480(4) . ?
C2 H2 1.0000 . ?
C2 C3 1.508(4) . ?
C2 C4 1.516(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.475(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.400(4) . ?
C5 C10 1.408(4) . ?
C6 C7 1.402(4) . ?
C6 C11 1.537(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.364(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.535(3) . ?
C11 C13 1.534(4) . ?
C11 C14 1.535(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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 N1 Cl1 114.12(17) . . ?
C1 N1 C5 123.9(2) . . ?
C5 N1 Cl1 111.84(17) . . ?
O1 C1 N1 121.5(2) . . ?
O1 C1 C2 123.6(2) . . ?
N1 C1 C2 114.9(2) . . ?
C1 C2 H2 117.5 . . ?
C1 C2 C3 116.6(3) . . ?
C1 C2 C4 115.9(2) . . ?
C3 C2 H2 117.5 . . ?
C3 C2 C4 58.39(18) . . ?
C4 C2 H2 117.5 . . ?
C2 C3 H3A 117.7 . . ?
C2 C3 H3B 117.7 . . ?
H3A C3 H3B 114.8 . . ?
C4 C3 C2 61.06(18) . . ?
C4 C3 H3A 117.7 . . ?
C4 C3 H3B 117.7 . . ?
C2 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
C3 C4 C2 60.55(18) . . ?
C3 C4 H4A 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C6 C5 N1 121.8(2) . . ?
C6 C5 C10 121.1(3) . . ?
C10 C5 N1 117.1(2) . . ?
C5 C6 C7 115.5(2) . . ?
C5 C6 C11 124.4(2) . . ?
C7 C6 C11 120.0(2) . . ?
C6 C7 H7 118.3 . . ?
C8 C7 C6 123.4(3) . . ?
C8 C7 H7 118.3 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.4 . . ?
C8 C9 C10 119.2(3) . . ?
C10 C9 H9 120.4 . . ?
C5 C10 H10 119.7 . . ?
C9 C10 C5 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C12 C11 C6 111.5(2) . . ?
C12 C11 C14 106.8(2) . . ?
C13 C11 C6 111.7(2) . . ?
C13 C11 C12 106.6(2) . . ?
C13 C11 C14 110.5(2) . . ?
C14 C11 C6 109.7(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
Cl1 N1 C1 O1 -13.8(4) . . . . ?
Cl1 N1 C1 C2 167.4(2) . . . . ?
Cl1 N1 C5 C6 100.5(2) . . . . ?
Cl1 N1 C5 C10 -77.9(2) . . . . ?
O1 C1 C2 C3 -17.6(4) . . . . ?
O1 C1 C2 C4 48.3(4) . . . . ?
N1 C1 C2 C3 161.2(2) . . . . ?
N1 C1 C2 C4 -132.9(3) . . . . ?
N1 C5 C6 C7 -178.1(2) . . . . ?
N1 C5 C6 C11 2.8(4) . . . . ?
N1 C5 C10 C9 177.7(2) . . . . ?
C1 N1 C5 C6 -116.4(3) . . . . ?
C1 N1 C5 C10 65.1(3) . . . . ?
C1 C2 C3 C4 105.4(3) . . . . ?
C1 C2 C4 C3 -106.6(3) . . . . ?
C5 N1 C1 O1 -156.1(3) . . . . ?
C5 N1 C1 C2 25.1(4) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C11 C12 -176.2(2) . . . . ?
C5 C6 C11 C13 -57.1(3) . . . . ?
C5 C6 C11 C14 65.8(3) . . . . ?
C6 C5 C10 C9 -0.8(4) . . . . ?
C6 C7 C8 C9 -0.8(4) . . . . ?
C7 C6 C11 C12 4.7(3) . . . . ?
C7 C6 C11 C13 123.8(3) . . . . ?
C7 C6 C11 C14 -113.3(3) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C5 0.4(4) . . . . ?
C10 C5 C6 C7 0.3(3) . . . . ?
C10 C5 C6 C11 -178.8(2) . . . . ?
C11 C6 C7 C8 179.6(2) . . . . ?

_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 1.459
_oxdiff_exptl_absorpt_empirical_full_min 0.519
####################################################################### 
# 
# 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_rja220003_fa
_database_code_depnum_ccdc_archive 'CCDC 2307647'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H22 Cl N O'
_chemical_formula_sum            'C19 H22 Cl N O'
_chemical_formula_weight         315.82
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H22 Cl1 N1 O1'
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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.7373(9)
_cell_length_b                   6.1891(2)
_cell_length_c                   18.0916(11)
_cell_angle_alpha                90
_cell_angle_beta                 110.509(6)
_cell_angle_gamma                90
_cell_volume                     1755.30(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12633
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      77.1450
_cell_measurement_theta_min      4.4180
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.635
_exptl_absorpt_coefficient_mu    1.923
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.60a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0227
0 0 -1 0.0227
-1 0 1 0.0245
1 0 -1 0.0245
0 2 1 0.1228
0 -2 -1 0.1228
1 0 0 0.0295
-1 0 0 0.0295
1 1 0 0.1090
-1 0 -1 0.0231
1 0 1 0.0231

_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
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
0.0060 -0.0004 0.9954 -0.0443 0.0779 0.0139
-0.0060 0.0004 -0.9954 0.0443 -0.0779 -0.0139
-1.0022 -0.0008 1.0039 0.0480 0.0956 -0.0170
1.0022 0.0008 -1.0039 -0.0480 -0.0956 0.0170
-0.0175 1.7788 0.9270 0.1003 0.0765 0.4325
0.0175 -1.7788 -0.9270 -0.1003 -0.0765 -0.4325
1.0082 0.0004 -0.0085 -0.0922 -0.0176 0.0309
-1.0082 -0.0004 0.0085 0.0922 0.0176 -0.0309
0.9965 0.8900 -0.0427 -0.0200 -0.0183 0.2402
-1.0142 -0.0001 -0.9868 0.1365 -0.0603 -0.0448
1.0142 0.0001 0.9868 -0.1365 0.0603 0.0448

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.948
_diffrn_reflns_theta_min         4.463
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -1.00   0.50    2.00    --  -48.75 -24.00  99.00  162
  2  ω   -117.00 -91.00   0.50    2.00    --  -48.75 -24.00  99.00   52
  3  ω    -21.00   5.00   0.50    2.00    --  -48.75  24.00 -95.00   52
  4  ω      6.00  34.00   0.50    2.00    --  -48.75  24.00 -95.00   56
  5  ω    -71.00 -45.00   0.50    2.00    --  -92.21 -24.00  99.00   52
  6  ω     98.00 152.00   0.50    2.00    --   96.68  24.00 -95.00  108
  7  ω     47.00  96.00   0.50    2.00    --   48.00  38.00 -60.00   98
  8  ω     43.00  68.00   0.50    2.00    --   48.00  24.00 -95.00   50
  9  ω    -25.00  34.00   0.50    2.00    --  -48.75  19.00   0.00  118
 10  ω   -126.00 -28.00   0.50    2.00    --  -48.75 -57.00  30.00  196
 11  ω     17.00  42.00   0.50    2.00    --   54.00  87.00  -7.61   50
 12  ω     17.00  42.00   0.50    2.00    --   54.00  88.00   6.56   50
 13  ω     17.00  42.00   0.50    2.00    --   54.00  88.00  50.90   50
 14  ω    -83.00 -55.00   0.50    2.00    --  -78.00 -67.00  27.38   56
 15  ω    -80.00 -51.00   0.50    2.00    --  -82.00 -77.00 -17.10   58
 16  ω    -76.00 -51.00   0.50    2.00    --  -82.00 -76.00 -45.79   50
 17  ω    -82.00 -56.00   0.50    2.00    --  -86.00 -76.00   6.40   52
 18  ω   -152.00 -94.00   0.50    2.00    --  -86.00 -77.00  -1.03  116
 19  ω    -90.00 -55.00   0.50    2.00    --  -86.00 -77.00  -1.03   70
 20  ω   -161.00 -60.00   0.50    2.00    --  -90.00 -77.00 -16.27  202
 21  ω    -88.00 -60.00   0.50    2.00    --  -90.00 -74.00  13.50   56
 22  ω   -122.00 -97.00   0.50    2.00    --  -90.00 -74.00  13.50   50
 23  ω   -103.00 -62.00   0.50    2.00    --  -90.00 -75.00 -46.06   82
 24  ω    -62.00 -21.00   0.50    2.00    --  -92.21 125.00 120.00   82
 25  ω    -92.00 -66.00   0.50    2.00    --  -92.21 125.00 120.00   52
 26  ω    -51.00 -16.00   0.50    2.00    --  -92.21  45.00 -30.00   70
 27  ω    -68.00 -23.00   0.50    2.00    --  -92.21  61.00  60.00   90
 28  ω    -93.00 -67.00   0.50    2.00    --  -92.21 -77.00  60.00   52
 29  ω    -35.00 -10.00   0.50    2.00    --  -92.21  30.00 -60.00   50
 30  ω   -168.00 -70.00   0.50    2.00    --  -92.21 -61.00  60.00  196
 31  ω    -35.00 -10.00   0.50    2.00    --  -92.21  30.00  90.00   50
 32  ω    -87.00 -62.00   0.50    2.00    --  -92.21 -77.00 -30.00   50
 33  ω    -89.00 -61.00   0.50    2.00    --  -92.21 -77.00  30.00   56
 34  ω    -70.00 -15.00   0.50    2.00    --  -92.21  61.00   0.00  110
 35  ω     19.00  50.00   0.50    2.00    --   96.68 -45.00 -30.00   62
 36  ω   -154.00 -69.00   0.50    2.00    --  -99.00 -75.00 -41.16  170
 37  ω     34.00  59.00   0.50    2.00    --  108.19 -61.00-180.00   50
 38  ω     35.00  60.00   0.50    2.00    --  108.19 -61.00  30.00   50
 39  ω     34.00  60.00   0.50    2.00    --  108.19 -61.00 120.00   52
 40  ω     61.00  87.00   0.50    2.00    --  108.19-125.00  60.00   52
 41  ω     39.00 105.00   0.50    2.00    --  108.19 -95.00 -60.00  132
 42  ω     31.00  57.00   0.50    2.00    --  108.19-125.00  60.00   52
 43  ω    148.00 174.00   0.50    2.00    --  108.19  77.00   0.00   52
 44  ω     81.00 123.00   0.50    2.00    --  108.19  77.00   0.00   84
 45  ω    119.00 144.00   0.50    2.00    --  108.19  24.00 -95.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0918998000
_diffrn_orient_matrix_UB_12      0.0783270000
_diffrn_orient_matrix_UB_13      -0.0438903000
_diffrn_orient_matrix_UB_21      -0.0168383000
_diffrn_orient_matrix_UB_22      0.0019995000
_diffrn_orient_matrix_UB_23      0.0784042000
_diffrn_orient_matrix_UB_31      0.0306426000
_diffrn_orient_matrix_UB_32      0.2362214000
_diffrn_orient_matrix_UB_33      0.0138874000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3016
_reflns_number_total             3493
_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 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.60a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0020(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3493
_refine_ls_number_restraints     234
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.180
_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)+(0.0611P)²+0.8242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1354
_refine_special_details          
;
The t-butyl group in this structure has been 
modelled as disordered over two positions. 
The occupancies of the two sites were 
refined independently of the atomic 
displacement parameters. The C-C bonds 
involving partially-occupied atoms were 
restrained using the SADI card and the 
displacement parameters of all partially-
occupied non-hydrogen atoms were 
restrained using the SIMU card.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C19B-C16 \\sim C19A-C16 \\sim C18B-C16 \\sim C18A-C16 \\sim C17B-C16 \\sim
C17A-C16
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C17A \\sim C18A \\sim C19A \\sim C17B \\sim C18B \\sim C19B: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: C17A(0.71929) H17A(0.71929) H17B(0.71929) H17C(0.71929)
 C18A(0.71929) H18A(0.71929) H18B(0.71929) H18C(0.71929) C19A(0.71929)
 H19A(0.71929) H19B(0.71929) H19C(0.71929) C17B(0.28071) H17D(0.28071)
 H17E(0.28071) H17F(0.28071) C18B(0.28071) H18D(0.28071) H18E(0.28071)
 H18F(0.28071) C19B(0.28071) H19D(0.28071) H19E(0.28071) H19F(0.28071)
6.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15)
6.c Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C19A(H19A,H19B,H19C), C17B(H17D,
 H17E,H17F), C18B(H18D,H18E,H18F), C19B(H19D,H19E,H19F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.33896(3) 0.23215(7) 0.43949(3) 0.04593(19) Uani 1 1 d . . . . .
O1 O 0.46985(9) 0.3970(2) 0.57352(8) 0.0429(3) Uani 1 1 d . . . . .
N1 N 0.34751(10) 0.4904(2) 0.47613(9) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.42000(11) 0.5379(3) 0.53860(10) 0.0350(4) Uani 1 1 d . . . . .
C2 C 0.43259(12) 0.7743(3) 0.55984(11) 0.0366(4) Uani 1 1 d . . . . .
H2A H 0.376189 0.842684 0.549282 0.044 Uiso 1 1 calc R U . . .
H2B H 0.459840 0.845514 0.525732 0.044 Uiso 1 1 calc R U . . .
C3 C 0.48779(13) 0.8112(3) 0.64640(11) 0.0415(4) Uani 1 1 d . . . . .
H3A H 0.540124 0.722483 0.659297 0.050 Uiso 1 1 calc R U . . .
H3B H 0.505284 0.964815 0.653809 0.050 Uiso 1 1 calc R U . . .
C4 C 0.44236(13) 0.7547(3) 0.70286(11) 0.0398(4) Uani 1 1 d . . . . .
C5 C 0.44904(13) 0.5508(3) 0.73670(11) 0.0446(5) Uani 1 1 d . . . . .
H5 H 0.482840 0.443757 0.724018 0.053 Uiso 1 1 calc R U . . .
C6 C 0.40736(16) 0.5004(4) 0.78863(13) 0.0568(6) Uani 1 1 d . . . . .
H6 H 0.413452 0.360903 0.811875 0.068 Uiso 1 1 calc R U . . .
C7 C 0.35699(19) 0.6540(5) 0.80634(16) 0.0688(7) Uani 1 1 d . . . . .
H7 H 0.328158 0.620205 0.841714 0.083 Uiso 1 1 calc R U . . .
C8 C 0.3486(2) 0.8560(5) 0.77267(16) 0.0713(7) Uani 1 1 d . . . . .
H8 H 0.313576 0.961326 0.784548 0.086 Uiso 1 1 calc R U . . .
C9 C 0.39123(16) 0.9065(4) 0.72133(13) 0.0573(6) Uani 1 1 d . . . . .
H9 H 0.385294 1.046671 0.698606 0.069 Uiso 1 1 calc R U . . .
C10 C 0.29166(11) 0.6411(3) 0.42104(10) 0.0334(4) Uani 1 1 d . . . . .
C11 C 0.20838(12) 0.6800(3) 0.41887(11) 0.0358(4) Uani 1 1 d . . . . .
C12 C 0.15992(12) 0.8163(3) 0.35755(11) 0.0414(4) Uani 1 1 d . . . . .
H12 H 0.102528 0.845629 0.352504 0.050 Uiso 1 1 calc R U . . .
C13 C 0.19160(12) 0.9097(3) 0.30418(11) 0.0423(5) Uani 1 1 d . . . . .
H13 H 0.156009 1.000804 0.263745 0.051 Uiso 1 1 calc R U . . .
C14 C 0.27480(12) 0.8717(3) 0.30916(10) 0.0382(4) Uani 1 1 d . . . . .
H14 H 0.297106 0.937327 0.273030 0.046 Uiso 1 1 calc R U . . .
C15 C 0.32461(12) 0.7363(3) 0.36779(11) 0.0342(4) Uani 1 1 d . . . . .
H15 H 0.381793 0.707509 0.371985 0.041 Uiso 1 1 calc R U . . .
C16 C 0.16507(13) 0.5852(4) 0.47383(13) 0.0490(5) Uani 1 1 d D . . . .
C17A C 0.1034(3) 0.4049(7) 0.4239(3) 0.0702(11) Uani 0.7193 1 d D U P A 1
H17A H 0.062492 0.469366 0.376125 0.105 Uiso 0.7193 1 calc R U P A 1
H17B H 0.072662 0.339224 0.455348 0.105 Uiso 0.7193 1 calc R U P A 1
H17C H 0.136771 0.293891 0.409059 0.105 Uiso 0.7193 1 calc R U P A 1
C18A C 0.2257(2) 0.4710(7) 0.5482(2) 0.0641(10) Uani 0.7193 1 d D U P A 1
H18A H 0.252009 0.346101 0.532454 0.096 Uiso 0.7193 1 calc R U P A 1
H18B H 0.193332 0.422478 0.580941 0.096 Uiso 0.7193 1 calc R U P A 1
H18C H 0.270304 0.572057 0.578362 0.096 Uiso 0.7193 1 calc R U P A 1
C19A C 0.1173(5) 0.7558(10) 0.4986(4) 0.0896(19) Uani 0.7193 1 d D U P A 1
H19A H 0.155309 0.878213 0.520836 0.134 Uiso 0.7193 1 calc R U P A 1
H19B H 0.096101 0.697377 0.538598 0.134 Uiso 0.7193 1 calc R U P A 1
H19C H 0.069117 0.804368 0.452791 0.134 Uiso 0.7193 1 calc R U P A 1
C17B C 0.1511(9) 0.3578(15) 0.4753(9) 0.082(3) Uani 0.2807 1 d D U P A 2
H17D H 0.123093 0.305188 0.421248 0.123 Uiso 0.2807 1 calc R U P A 2
H17E H 0.114634 0.328287 0.506304 0.123 Uiso 0.2807 1 calc R U P A 2
H17F H 0.205916 0.284019 0.499297 0.123 Uiso 0.2807 1 calc R U P A 2
C18B C 0.2151(7) 0.682(2) 0.5622(5) 0.075(3) Uani 0.2807 1 d D U P A 2
H18D H 0.273632 0.626188 0.582000 0.113 Uiso 0.2807 1 calc R U P A 2
H18E H 0.185356 0.636998 0.597660 0.113 Uiso 0.2807 1 calc R U P A 2
H18F H 0.216285 0.839849 0.559823 0.113 Uiso 0.2807 1 calc R U P A 2
C19B C 0.0774(8) 0.707(2) 0.4623(10) 0.076(4) Uani 0.2807 1 d D U P A 2
H19D H 0.087204 0.862919 0.466456 0.113 Uiso 0.2807 1 calc R U P A 2
H19E H 0.055436 0.659458 0.503301 0.113 Uiso 0.2807 1 calc R U P A 2
H19F H 0.035794 0.671788 0.410233 0.113 Uiso 0.2807 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7171(16) . ?
O1 C1 1.219(2) . ?
N1 C1 1.369(2) . ?
N1 C10 1.444(2) . ?
C1 C2 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.513(3) . ?
C4 C5 1.390(3) . ?
C4 C9 1.388(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.381(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.377(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(3) . ?
C10 C15 1.397(3) . ?
C11 C12 1.403(3) . ?
C11 C16 1.537(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17A 1.572(4) . ?
C16 C18A 1.544(4) . ?
C16 C19A 1.485(6) . ?
C16 C17B 1.429(9) . ?
C16 C18B 1.636(9) . ?
C16 C19B 1.595(11) . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?

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 N1 Cl1 116.63(13) . . ?
C1 N1 C10 127.11(15) . . ?
C10 N1 Cl1 112.88(12) . . ?
O1 C1 N1 121.46(18) . . ?
O1 C1 C2 123.55(17) . . ?
N1 C1 C2 114.99(15) . . ?
C1 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C1 C2 C3 112.66(16) . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 H2A 109.1 . . ?
C3 C2 H2B 109.1 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 112.97(16) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 C4 C3 121.69(19) . . ?
C9 C4 C3 120.3(2) . . ?
C9 C4 C5 118.0(2) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 120.2 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 119.9(2) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 C8 120.8(2) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 N1 121.83(16) . . ?
C15 C10 N1 115.59(16) . . ?
C15 C10 C11 122.50(16) . . ?
C10 C11 C12 114.78(17) . . ?
C10 C11 C16 127.30(17) . . ?
C12 C11 C16 117.88(17) . . ?
C11 C12 H12 118.4 . . ?
C13 C12 C11 123.18(18) . . ?
C13 C12 H12 118.4 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.50(18) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.47(18) . . ?
C15 C14 H14 120.8 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.54(18) . . ?
C14 C15 H15 119.7 . . ?
C11 C16 C17A 105.2(2) . . ?
C11 C16 C18A 115.04(19) . . ?
C11 C16 C18B 107.3(4) . . ?
C11 C16 C19B 110.9(6) . . ?
C18A C16 C17A 105.9(3) . . ?
C19A C16 C11 110.5(3) . . ?
C19A C16 C17A 111.3(4) . . ?
C19A C16 C18A 108.7(3) . . ?
C17B C16 C11 120.4(5) . . ?
C17B C16 C18B 111.9(8) . . ?
C17B C16 C19B 108.5(8) . . ?
C19B C16 C18B 95.0(8) . . ?
C16 C17A H17A 109.5 . . ?
C16 C17A H17B 109.5 . . ?
C16 C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C16 C18A H18A 109.5 . . ?
C16 C18A H18B 109.5 . . ?
C16 C18A H18C 109.5 . . ?
H18A C18A H18B 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C16 C19A H19A 109.5 . . ?
C16 C19A H19B 109.5 . . ?
C16 C19A H19C 109.5 . . ?
H19A C19A H19B 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C16 C17B H17D 109.5 . . ?
C16 C17B H17E 109.5 . . ?
C16 C17B H17F 109.5 . . ?
H17D C17B H17E 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C16 C18B H18D 109.5 . . ?
C16 C18B H18E 109.5 . . ?
C16 C18B H18F 109.5 . . ?
H18D C18B H18E 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C16 C19B H19D 109.5 . . ?
C16 C19B H19E 109.5 . . ?
C16 C19B H19F 109.5 . . ?
H19D C19B H19E 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

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
Cl1 N1 C1 O1 -10.2(2) . . . . ?
Cl1 N1 C1 C2 169.66(13) . . . . ?
Cl1 N1 C10 C11 89.75(19) . . . . ?
Cl1 N1 C10 C15 -87.10(17) . . . . ?
O1 C1 C2 C3 -25.4(3) . . . . ?
N1 C1 C2 C3 154.69(17) . . . . ?
N1 C10 C11 C12 -174.66(16) . . . . ?
N1 C10 C11 C16 3.3(3) . . . . ?
N1 C10 C15 C14 175.67(16) . . . . ?
C1 N1 C10 C11 -111.9(2) . . . . ?
C1 N1 C10 C15 71.2(2) . . . . ?
C1 C2 C3 C4 -72.1(2) . . . . ?
C2 C3 C4 C5 92.7(2) . . . . ?
C2 C3 C4 C9 -86.3(2) . . . . ?
C3 C4 C5 C6 179.81(19) . . . . ?
C3 C4 C9 C8 179.5(2) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C4 C9 C8 0.5(3) . . . . ?
C5 C6 C7 C8 -0.2(4) . . . . ?
C6 C7 C8 C9 -0.5(4) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C10 N1 C1 O1 -167.83(18) . . . . ?
C10 N1 C1 C2 12.0(3) . . . . ?
C10 C11 C12 C13 -1.4(3) . . . . ?
C10 C11 C16 C17A -103.6(3) . . . . ?
C10 C11 C16 C18A 12.5(3) . . . . ?
C10 C11 C16 C19A 136.1(4) . . . . ?
C10 C11 C16 C17B -63.3(8) . . . . ?
C10 C11 C16 C18B 66.1(6) . . . . ?
C10 C11 C16 C19B 168.6(7) . . . . ?
C11 C10 C15 C14 -1.2(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C11 C16 C17A 74.2(3) . . . . ?
C12 C11 C16 C18A -169.6(3) . . . . ?
C12 C11 C16 C19A -46.0(4) . . . . ?
C12 C11 C16 C17B 114.6(8) . . . . ?
C12 C11 C16 C18B -116.1(5) . . . . ?
C12 C11 C16 C19B -13.5(7) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C10 -0.4(3) . . . . ?
C15 C10 C11 C12 2.0(3) . . . . ?
C15 C10 C11 C16 179.89(18) . . . . ?
C16 C11 C12 C13 -179.54(19) . . . . ?

_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 1.995
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_rja230002_fa
_database_code_depnum_ccdc_archive 'CCDC 2307645'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 Cl N O'
_chemical_formula_sum            'C15 H20 Cl N O'
_chemical_formula_weight         265.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H30 Cl1 N1 O1'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.0047(5)
_cell_length_b                   6.6560(2)
_cell_length_c                   24.7570(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.075(3)
_cell_angle_gamma                90
_cell_volume                     2800.24(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5924
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      76.5020
_cell_measurement_theta_min      3.5680
_shelx_estimated_absorpt_T_max   0.802
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    2.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.744
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0500
0 0 1 0.0480
-1 0 0 0.0782
1 0 0 0.0782
0 1 -1 0.0802
0 -1 1 0.0742
-1 -1 1 0.0670
1 -1 -1 0.0958
1 1 1 0.0961

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
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
-0.0000 -0.0000 -1.0000 -0.0418 0.0461 0.0033
0.0000 0.0000 1.0000 0.0418 -0.0461 -0.0033
-1.0000 0.0000 -0.0000 -0.0252 -0.0244 0.0835
1.0000 -0.0000 0.0000 0.0252 0.0244 -0.0835
-0.0000 1.0000 -1.0000 0.1194 0.1860 0.0929
0.0000 -1.0000 1.0000 -0.1194 -0.1860 -0.0929
-1.0000 -1.0000 1.0000 -0.1446 -0.2104 -0.0093
1.0000 -1.0000 -1.0000 -0.1778 -0.0694 -0.1699
1.0000 1.0000 1.0000 0.2282 0.1183 0.0028

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.220
_diffrn_reflns_theta_min         3.573
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00  15.00   0.50    0.05    --  -49.76  93.00 -82.00  174
  2  ω   -105.00 -24.00   0.50    0.05    --  -92.01  93.00 -82.00  162
  3  ω     -5.00  24.00   0.50    0.05    --  -49.76  19.00 -90.00   58
  4  ω     74.00 119.00   0.50    0.05    --   48.76 125.00-180.00   90
  5  ω     75.00 119.00   0.50    0.05    --   48.76 125.00 -60.00   88
  6  ω     83.00 140.00   0.50    0.05    --   96.11  93.00 -82.00  114
  7  ω     98.00 130.00   0.50    0.05    --  108.00  45.00 -90.00   64
  8  ω    143.00 169.00   0.50    0.05    --   96.11  61.00   0.00   52
  9  ω    109.00 144.00   0.50    0.05    --  108.00  77.00  30.00   70
 10  ω     92.00 131.00   0.50    0.05    --   96.11  61.00   0.00   78
 11  ω     19.00  51.00   0.50    0.05    --   96.11 -45.00 -60.00   64
 12  ω     21.00  51.00   0.50    0.05    --   96.11 -45.00-150.00   60
 13  ω     44.00  69.00   0.50    0.05    --  108.00 -61.00-180.00   50
 14  ω     34.00  60.00   0.50    0.05    --  108.00 -61.00-120.00   52
 15  ω     39.00  64.00   0.50    0.05    --  108.00 -61.00 -60.00   50
 16  ω     38.00  70.00   0.50    0.05    --  108.00 -61.00  60.00   64
 17  ω     27.00 108.00   0.50    0.05    --   96.11-125.00 150.00  162
 18  ω     28.00  63.00   0.50    0.05    --   96.11 -95.00  30.00   70
 19  ω     62.00  87.00   0.50    0.05    --  108.00 -93.00 165.00   50
 20  ω     29.00  98.00   0.50    0.05    --   96.11 -93.00 165.00  138
 21  ω     -9.00  66.00   0.50    0.05    --   48.76 -93.00 165.00  150
 22  ω   -120.00 -32.00   0.50    0.05    --  -49.76 -57.00   0.00  176
 23  ω   -160.00 -65.00   0.50    0.05    --  -92.01 -77.00-120.00  190
 24  ω   -160.00 -83.00   0.50    0.05    --  -92.01 -95.00  60.00  154
 25  ω   -153.00 -66.00   0.50    0.05    --  -92.01 -77.00 120.00  174
 26  ω   -133.00 -83.00   0.50    0.05    --  -92.01 -93.00 165.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0251893000
_diffrn_orient_matrix_UB_12      0.1612047000
_diffrn_orient_matrix_UB_13      0.0417860000
_diffrn_orient_matrix_UB_21      0.0244216000
_diffrn_orient_matrix_UB_22      0.1399175000
_diffrn_orient_matrix_UB_23      -0.0460762000
_diffrn_orient_matrix_UB_31      -0.0835409000
_diffrn_orient_matrix_UB_32      0.0895847000
_diffrn_orient_matrix_UB_33      -0.0032721000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2466
_reflns_number_total             2785
_reflns_odcompleteness_completeness 99.78
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.066
_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)+(0.0480P)²+1.3382P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0928
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77236(2) -0.04092(5) 0.36723(2) 0.03418(13) Uani 1 1 d . . . . .
O1 O 0.61882(6) 0.10794(17) 0.38092(5) 0.0424(3) Uani 1 1 d . . . . .
N1 N 0.74464(6) 0.20823(16) 0.36933(5) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.66458(8) 0.2423(2) 0.37137(6) 0.0292(3) Uani 1 1 d . . . . .
C2 C 0.63845(8) 0.4565(2) 0.36178(6) 0.0292(3) Uani 1 1 d . . . . .
H2 H 0.684118 0.551100 0.361580 0.035 Uiso 1 1 calc R U . . .
C3 C 0.57194(9) 0.5358(2) 0.39707(6) 0.0363(4) Uani 1 1 d . . . . .
H3A H 0.540180 0.428505 0.413334 0.044 Uiso 1 1 calc R U . . .
H3B H 0.589884 0.634970 0.424667 0.044 Uiso 1 1 calc R U . . .
C4 C 0.53289(9) 0.6309(3) 0.34620(7) 0.0402(4) Uani 1 1 d . . . . .
H4A H 0.545756 0.774677 0.341371 0.048 Uiso 1 1 calc R U . . .
H4B H 0.475431 0.607803 0.342580 0.048 Uiso 1 1 calc R U . . .
C5 C 0.58196(9) 0.4874(2) 0.31190(6) 0.0358(3) Uani 1 1 d . . . . .
H5A H 0.606804 0.553400 0.281005 0.043 Uiso 1 1 calc R U . . .
H5B H 0.553492 0.364188 0.300233 0.043 Uiso 1 1 calc R U . . .
C6 C 0.80063(7) 0.34365(19) 0.34594(5) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.85207(7) 0.46147(18) 0.37846(5) 0.0217(3) Uani 1 1 d . . . . .
C8 C 0.90309(8) 0.5839(2) 0.34991(6) 0.0293(3) Uani 1 1 d . . . . .
H8 H 0.938710 0.668339 0.369759 0.035 Uiso 1 1 calc R U . . .
C9 C 0.90387(8) 0.5873(2) 0.29408(6) 0.0348(3) Uani 1 1 d . . . . .
H9 H 0.939752 0.672993 0.276663 0.042 Uiso 1 1 calc R U . . .
C10 C 0.85335(9) 0.4681(2) 0.26335(6) 0.0327(3) Uani 1 1 d . . . . .
H10 H 0.854326 0.469444 0.225008 0.039 Uiso 1 1 calc R U . . .
C11 C 0.80123(8) 0.3467(2) 0.28979(5) 0.0287(3) Uani 1 1 d . . . . .
H11 H 0.765452 0.264417 0.269408 0.034 Uiso 1 1 calc R U . . .
C12 C 0.85684(8) 0.45847(19) 0.44080(5) 0.0250(3) Uani 1 1 d . . . . .
C13 C 0.88753(8) 0.2528(2) 0.46044(5) 0.0295(3) Uani 1 1 d . . . . .
H13A H 0.849933 0.147981 0.449176 0.044 Uiso 1 1 calc R U . . .
H13B H 0.893715 0.253659 0.499946 0.044 Uiso 1 1 calc R U . . .
H13C H 0.938520 0.225687 0.444703 0.044 Uiso 1 1 calc R U . . .
C14 C 0.77685(9) 0.5013(2) 0.46553(6) 0.0318(3) Uani 1 1 d . . . . .
H14A H 0.755894 0.628740 0.451357 0.048 Uiso 1 1 calc R U . . .
H14B H 0.783636 0.510019 0.504935 0.048 Uiso 1 1 calc R U . . .
H14C H 0.740078 0.392474 0.456041 0.048 Uiso 1 1 calc R U . . .
C15 C 0.91424(9) 0.6183(2) 0.46325(6) 0.0367(3) Uani 1 1 d . . . . .
H15A H 0.966782 0.593037 0.449725 0.055 Uiso 1 1 calc R U . . .
H15B H 0.916364 0.612136 0.502826 0.055 Uiso 1 1 calc R U . . .
H15C H 0.896226 0.751726 0.451541 0.055 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7253(11) . ?
O1 C1 1.2145(17) . ?
N1 C1 1.3828(17) . ?
N1 C6 1.4470(16) . ?
C1 C2 1.5091(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.5470(19) . ?
C2 C5 1.550(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.538(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.543(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4061(18) . ?
C6 C11 1.3906(18) . ?
C7 C8 1.4003(18) . ?
C7 C12 1.5427(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.5377(18) . ?
C12 C14 1.5383(19) . ?
C12 C15 1.5342(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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 N1 Cl1 115.43(9) . . ?
C1 N1 C6 125.11(11) . . ?
C6 N1 Cl1 113.72(8) . . ?
O1 C1 N1 121.65(13) . . ?
O1 C1 C2 122.63(13) . . ?
N1 C1 C2 115.72(11) . . ?
C1 C2 H2 111.8 . . ?
C1 C2 C3 116.80(12) . . ?
C1 C2 C5 114.90(12) . . ?
C3 C2 H2 111.8 . . ?
C3 C2 C5 87.70(11) . . ?
C5 C2 H2 111.8 . . ?
C2 C3 H3A 113.8 . . ?
C2 C3 H3B 113.8 . . ?
H3A C3 H3B 111.1 . . ?
C4 C3 C2 88.90(11) . . ?
C4 C3 H3A 113.8 . . ?
C4 C3 H3B 113.8 . . ?
C3 C4 H4A 113.9 . . ?
C3 C4 H4B 113.9 . . ?
C3 C4 C5 88.28(11) . . ?
H4A C4 H4B 111.1 . . ?
C5 C4 H4A 113.9 . . ?
C5 C4 H4B 113.9 . . ?
C2 C5 H5A 113.9 . . ?
C2 C5 H5B 113.9 . . ?
C4 C5 C2 88.61(11) . . ?
C4 C5 H5A 113.9 . . ?
C4 C5 H5B 113.9 . . ?
H5A C5 H5B 111.1 . . ?
C7 C6 N1 121.54(11) . . ?
C11 C6 N1 115.96(11) . . ?
C11 C6 C7 122.49(12) . . ?
C6 C7 C12 125.07(11) . . ?
C8 C7 C6 114.82(12) . . ?
C8 C7 C12 120.09(12) . . ?
C7 C8 H8 118.6 . . ?
C9 C8 C7 122.85(13) . . ?
C9 C8 H8 118.6 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.94(13) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.22(13) . . ?
C11 C10 H10 120.9 . . ?
C6 C11 H11 119.7 . . ?
C10 C11 C6 120.67(13) . . ?
C10 C11 H11 119.7 . . ?
C13 C12 C7 109.44(10) . . ?
C13 C12 C14 109.52(11) . . ?
C14 C12 C7 112.37(11) . . ?
C15 C12 C7 111.30(11) . . ?
C15 C12 C13 107.36(11) . . ?
C15 C12 C14 106.70(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
Cl1 N1 C1 O1 12.82(18) . . . . ?
Cl1 N1 C1 C2 -168.00(10) . . . . ?
Cl1 N1 C6 C7 -103.18(12) . . . . ?
Cl1 N1 C6 C11 75.64(13) . . . . ?
O1 C1 C2 C3 38.5(2) . . . . ?
O1 C1 C2 C5 -62.14(19) . . . . ?
N1 C1 C2 C3 -140.65(13) . . . . ?
N1 C1 C2 C5 118.70(13) . . . . ?
N1 C6 C7 C8 179.60(11) . . . . ?
N1 C6 C7 C12 1.48(19) . . . . ?
N1 C6 C11 C10 -178.89(12) . . . . ?
C1 N1 C6 C7 104.92(15) . . . . ?
C1 N1 C6 C11 -76.26(16) . . . . ?
C1 C2 C3 C4 -135.97(13) . . . . ?
C1 C2 C5 C4 137.66(12) . . . . ?
C2 C3 C4 C5 19.20(12) . . . . ?
C3 C2 C5 C4 19.06(12) . . . . ?
C3 C4 C5 C2 -19.16(12) . . . . ?
C5 C2 C3 C4 -19.11(12) . . . . ?
C6 N1 C1 O1 164.30(13) . . . . ?
C6 N1 C1 C2 -16.53(19) . . . . ?
C6 C7 C8 C9 -0.9(2) . . . . ?
C6 C7 C12 C13 66.34(16) . . . . ?
C6 C7 C12 C14 -55.56(16) . . . . ?
C6 C7 C12 C15 -175.15(12) . . . . ?
C7 C6 C11 C10 -0.1(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C8 C7 C12 C13 -111.68(14) . . . . ?
C8 C7 C12 C14 126.42(13) . . . . ?
C8 C7 C12 C15 6.83(17) . . . . ?
C8 C9 C10 C11 0.7(2) . . . . ?
C9 C10 C11 C6 -0.7(2) . . . . ?
C11 C6 C7 C8 0.85(18) . . . . ?
C11 C6 C7 C12 -177.26(12) . . . . ?
C12 C7 C8 C9 177.35(13) . . . . ?

_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 1.224
_oxdiff_exptl_absorpt_empirical_full_min 0.865
####################################################################### 
# 
# 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_rja230006_2_fa
_database_code_depnum_ccdc_archive 'CCDC 2307643'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-17
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 Cl N O'
_chemical_formula_sum            'C16 H22 Cl N O'
_chemical_formula_weight         279.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H21 Cl1 N1 O1'
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                   12.6132(6)
_cell_length_b                   6.8258(4)
_cell_length_c                   17.3255(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.319(4)
_cell_angle_gamma                90
_cell_volume                     1489.13(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8454
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.9530
_cell_measurement_theta_min      3.5010
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.656
_exptl_absorpt_coefficient_mu    2.195
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             600
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0112
0 0 1 0.0112
-1 1 1 0.0432
1 -1 -1 0.0432
-1 -1 0 0.0713
1 1 0 0.1183
1 0 0 0.1041
-1 0 0 0.0771

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
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
-0.0000 -0.0000 -1.0001 0.0005 0.0886 0.0091
0.0000 0.0000 1.0001 -0.0005 -0.0886 -0.0091
-1.0000 1.0000 1.0004 -0.2502 -0.0741 -0.0675
1.0000 -1.0000 -1.0004 0.2502 0.0741 0.0675
-1.0000 -1.0000 0.0001 0.1869 0.0242 -0.1747
1.0000 1.0000 -0.0001 -0.1869 -0.0242 0.1747
1.0000 -0.0000 -0.0002 0.0314 -0.0193 0.1166
-1.0000 0.0000 0.0002 -0.0314 0.0193 -0.1166

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.934
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.217
_diffrn_reflns_theta_min         3.510
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     83.00 178.00   0.50    1.14    --  108.00 106.00  50.00  190
  2  ω     83.00 167.00   0.50    1.14    --   96.11 106.00  50.00  168
  3  ω     74.00 121.00   0.50    1.14    --   48.51 125.00-120.00   94
  4  ω     74.00 121.00   0.50    1.14    --   48.51 125.00-180.00   94
  5  ω     -2.00  92.00   0.50    1.14    --   48.51-106.00 -48.00  188
  6  ω     36.00 111.00   0.50    1.14    --  108.00-125.00 -90.00  150
  7  ω     25.00 107.00   0.50    1.14    --   96.11-106.00 -48.00  164
  8  ω     37.00 107.00   0.50    1.14    --  108.00-106.00 -48.00  140
  9  ω     40.00 105.00   0.50    1.14    --  108.00 -77.00   0.00  130
 10  ω     34.00  71.00   0.50    1.14    --  108.00 -61.00  90.00   74
 11  ω     18.00  51.00   0.50    1.14    --   96.11 -45.00  90.00   66
 12  ω     18.00  51.00   0.50    1.14    --   96.11 -45.00 120.00   66
 13  ω   -118.00 -23.00   0.50    1.14    --  -49.38 -77.00  30.00  190
 14  ω   -163.00 -83.00   0.50    1.14    --  -92.01-106.00 -48.00  160
 15  ω   -118.00 -44.00   0.50    1.14    --  -49.38 -77.00 -90.00  148
 16  ω   -118.00 -23.00   0.50    1.14    --  -49.38 -77.00 150.00  190
 17  ω    -92.00   2.00   0.50    1.14    --  -49.38 106.00  50.00  188
 18  ω   -107.00 -21.00   0.50    1.14    --  -92.01 106.00  50.00  172
 19  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00  30.00   74
 20  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00  60.00   74
 21  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00   0.00   74
 22  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00 -30.00   74
 23  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00 -90.00   74
 24  ω    -51.00 -14.00   0.50    1.14    --  -92.01  45.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0314038000
_diffrn_orient_matrix_UB_12      -0.2183094000
_diffrn_orient_matrix_UB_13      -0.0004598000
_diffrn_orient_matrix_UB_21      -0.0193117000
_diffrn_orient_matrix_UB_22      -0.0048487000
_diffrn_orient_matrix_UB_23      -0.0885527000
_diffrn_orient_matrix_UB_31      0.1165503000
_diffrn_orient_matrix_UB_32      0.0581875000
_diffrn_orient_matrix_UB_33      -0.0090890000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2426
_reflns_number_total             2982
_reflns_odcompleteness_completeness 99.90
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.046
_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)+(0.0633P)²+0.8209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1337
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.73708(5) 0.62407(7) 0.78162(3) 0.05060(19) Uani 1 1 d . . . . .
O1 O 0.73744(15) 0.5152(2) 0.62681(9) 0.0579(4) Uani 1 1 d . . . . .
N1 N 0.74495(14) 0.3860(2) 0.74727(10) 0.0398(4) Uani 1 1 d . . . . .
C1 C 0.73459(16) 0.3707(3) 0.66707(11) 0.0399(5) Uani 1 1 d . . . . .
C2 C 0.72471(16) 0.1660(3) 0.63494(11) 0.0388(4) Uani 1 1 d . . . . .
H2 H 0.735095 0.069524 0.676596 0.047 Uiso 1 1 calc R U . . .
C3 C 0.61769(17) 0.1316(4) 0.59004(14) 0.0508(6) Uani 1 1 d . . . . .
H3A H 0.564236 0.090369 0.624684 0.061 Uiso 1 1 calc R U . . .
H3B H 0.593529 0.250342 0.563781 0.061 Uiso 1 1 calc R U . . .
C4 C 0.63838(19) -0.0293(4) 0.53177(15) 0.0600(6) Uani 1 1 d . . . . .
H4A H 0.607060 -0.151798 0.547415 0.072 Uiso 1 1 calc R U . . .
H4B H 0.607702 0.005786 0.481018 0.072 Uiso 1 1 calc R U . . .
C5 C 0.75785(18) -0.0499(3) 0.52983(13) 0.0485(5) Uani 1 1 d . . . . .
H5A H 0.779213 -0.052298 0.476951 0.058 Uiso 1 1 calc R U . . .
H5B H 0.781945 -0.169485 0.555512 0.058 Uiso 1 1 calc R U . . .
C6 C 0.80350(16) 0.1294(3) 0.57248(11) 0.0404(5) Uani 1 1 d . . . . .
H6A H 0.806808 0.240880 0.538006 0.049 Uiso 1 1 calc R U . . .
H6B H 0.874072 0.102840 0.595321 0.049 Uiso 1 1 calc R U . . .
C7 C 0.70214(15) 0.2442(3) 0.79972(11) 0.0374(4) Uani 1 1 d . . . . .
C8 C 0.76833(15) 0.1256(3) 0.84852(10) 0.0355(4) Uani 1 1 d . . . . .
C9 C 0.71525(17) 0.0057(3) 0.89889(12) 0.0429(5) Uani 1 1 d . . . . .
H9 H 0.755097 -0.075335 0.932543 0.051 Uiso 1 1 calc R U . . .
C10 C 0.60520(18) 0.0026(3) 0.90083(13) 0.0487(5) Uani 1 1 d . . . . .
H10 H 0.573335 -0.078316 0.935944 0.058 Uiso 1 1 calc R U . . .
C11 C 0.54312(17) 0.1176(3) 0.85146(13) 0.0482(5) Uani 1 1 d . . . . .
H11 H 0.469467 0.113286 0.851949 0.058 Uiso 1 1 calc R U . . .
C12 C 0.59215(16) 0.2393(3) 0.80124(12) 0.0442(5) Uani 1 1 d . . . . .
H12 H 0.551169 0.319313 0.767888 0.053 Uiso 1 1 calc R U . . .
C13 C 0.89081(15) 0.1227(3) 0.85007(11) 0.0374(4) Uani 1 1 d . . . . .
C14 C 0.93652(18) -0.0410(4) 0.90205(13) 0.0501(5) Uani 1 1 d . . . . .
H14A H 0.916058 -0.020570 0.953950 0.075 Uiso 1 1 calc R U . . .
H14B H 1.012576 -0.040370 0.901400 0.075 Uiso 1 1 calc R U . . .
H14C H 0.909676 -0.164958 0.883468 0.075 Uiso 1 1 calc R U . . .
C15 C 0.93617(17) 0.3173(3) 0.88129(12) 0.0443(5) Uani 1 1 d . . . . .
H15A H 0.908512 0.422953 0.849569 0.067 Uiso 1 1 calc R U . . .
H15B H 1.012195 0.315035 0.880417 0.067 Uiso 1 1 calc R U . . .
H15C H 0.916224 0.335820 0.933425 0.067 Uiso 1 1 calc R U . . .
C16 C 0.93120(17) 0.0864(3) 0.76936(12) 0.0445(5) Uani 1 1 d . . . . .
H16A H 0.900005 -0.031546 0.748157 0.067 Uiso 1 1 calc R U . . .
H16B H 1.007097 0.073300 0.773237 0.067 Uiso 1 1 calc R U . . .
H16C H 0.911735 0.194920 0.736236 0.067 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7352(17) . ?
O1 C1 1.209(2) . ?
N1 C1 1.392(3) . ?
N1 C7 1.453(3) . ?
C1 C2 1.507(3) . ?
C2 H2 0.9800 . ?
C2 C3 1.537(3) . ?
C2 C6 1.531(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.524(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.516(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.525(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.409(3) . ?
C7 C12 1.389(3) . ?
C8 C9 1.395(3) . ?
C8 C13 1.544(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.372(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.527(3) . ?
C13 C15 1.533(3) . ?
C13 C16 1.536(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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 N1 Cl1 114.12(14) . . ?
C1 N1 C7 123.88(16) . . ?
C7 N1 Cl1 112.26(13) . . ?
O1 C1 N1 120.69(19) . . ?
O1 C1 C2 123.20(18) . . ?
N1 C1 C2 116.06(17) . . ?
C1 C2 H2 110.3 . . ?
C1 C2 C3 112.34(17) . . ?
C1 C2 C6 111.66(17) . . ?
C3 C2 H2 110.3 . . ?
C6 C2 H2 110.3 . . ?
C6 C2 C3 101.79(16) . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.44(18) . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C3 C4 H4A 110.4 . . ?
C3 C4 H4B 110.4 . . ?
H4A C4 H4B 108.6 . . ?
C5 C4 C3 106.86(19) . . ?
C5 C4 H4A 110.4 . . ?
C5 C4 H4B 110.4 . . ?
C4 C5 H5A 110.7 . . ?
C4 C5 H5B 110.7 . . ?
C4 C5 C6 105.24(18) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
C2 C6 H6A 111.1 . . ?
C2 C6 H6B 111.1 . . ?
C5 C6 C2 103.36(16) . . ?
C5 C6 H6A 111.1 . . ?
C5 C6 H6B 111.1 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 N1 121.95(17) . . ?
C12 C7 N1 115.82(18) . . ?
C12 C7 C8 122.16(18) . . ?
C7 C8 C13 125.14(17) . . ?
C9 C8 C7 115.03(18) . . ?
C9 C8 C13 119.83(18) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.7(2) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C8 111.30(17) . . ?
C14 C13 C15 107.80(17) . . ?
C14 C13 C16 106.58(17) . . ?
C15 C13 C8 110.34(16) . . ?
C15 C13 C16 108.91(17) . . ?
C16 C13 C8 111.75(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
Cl1 N1 C1 O1 11.2(3) . . . . ?
Cl1 N1 C1 C2 -171.32(14) . . . . ?
Cl1 N1 C7 C8 -102.90(18) . . . . ?
Cl1 N1 C7 C12 74.26(19) . . . . ?
O1 C1 C2 C3 -65.5(3) . . . . ?
O1 C1 C2 C6 48.2(3) . . . . ?
N1 C1 C2 C3 117.1(2) . . . . ?
N1 C1 C2 C6 -129.24(19) . . . . ?
N1 C7 C8 C9 176.13(17) . . . . ?
N1 C7 C8 C13 -3.1(3) . . . . ?
N1 C7 C12 C11 -176.79(18) . . . . ?
C1 N1 C7 C8 113.3(2) . . . . ?
C1 N1 C7 C12 -69.5(3) . . . . ?
C1 C2 C3 C4 153.51(19) . . . . ?
C1 C2 C6 C5 -161.75(17) . . . . ?
C2 C3 C4 C5 -13.4(3) . . . . ?
C3 C2 C6 C5 -41.7(2) . . . . ?
C3 C4 C5 C6 -12.7(3) . . . . ?
C4 C5 C6 C2 34.0(2) . . . . ?
C6 C2 C3 C4 33.9(2) . . . . ?
C7 N1 C1 O1 154.4(2) . . . . ?
C7 N1 C1 C2 -28.1(3) . . . . ?
C7 C8 C9 C10 0.2(3) . . . . ?
C7 C8 C13 C14 -172.60(18) . . . . ?
C7 C8 C13 C15 67.8(2) . . . . ?
C7 C8 C13 C16 -53.6(3) . . . . ?
C8 C7 C12 C11 0.4(3) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
C9 C8 C13 C14 8.2(2) . . . . ?
C9 C8 C13 C15 -111.5(2) . . . . ?
C9 C8 C13 C16 127.2(2) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C12 C7 C8 C9 -0.8(3) . . . . ?
C12 C7 C8 C13 179.90(18) . . . . ?
C13 C8 C9 C10 179.49(19) . . . . ?

_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 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.752
####################################################################### 
# 
# 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_rja220004_fa
_database_code_depnum_ccdc_archive 'CCDC 2307646'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2022-11-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 Cl N O'
_chemical_formula_sum            'C17 H18 Cl N O'
_chemical_formula_weight         287.77
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H18 Cl1 N1 O1'
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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.63450(10)
_cell_length_b                   9.62950(10)
_cell_length_c                   20.4737(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1505.15(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12444
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      78.2760
_cell_measurement_theta_min      2.1840
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    2.194
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.0751
0 -1 0 0.0811
-1 0 0 0.0983
1 0 0 0.0623
-1 -1 0 0.0825
1 1 0 0.0695
0 0 1 0.0411
0 0 -1 0.0411
0 1 -1 0.0710
0 -1 1 0.0710
-1 0 1 0.0904
1 0 -1 0.0514
-1 -1 2 0.0789
1 1 -2 0.0509
0 -1 -2 0.0647

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
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
0.0011 0.9998 -0.0004 0.1139 0.0290 0.1085
-0.0011 -0.9998 0.0004 -0.1139 -0.0290 -0.1085
-0.9999 0.0003 0.0000 -0.1295 -0.0457 0.1478
0.9999 -0.0003 -0.0000 0.1295 0.0457 -0.1478
-1.0010 -0.9995 0.0005 -0.2434 -0.0747 0.0393
1.0010 0.9995 -0.0005 0.2434 0.0747 -0.0393
-0.0000 0.0001 1.0004 0.0216 -0.0720 -0.0034
0.0000 -0.0001 -1.0004 -0.0216 0.0720 0.0034
0.0011 0.9997 -1.0008 0.0923 0.1011 0.1119
-0.0011 -0.9997 1.0008 -0.0923 -0.1011 -0.1119
-1.0000 0.0004 1.0004 -0.1079 -0.1177 0.1444
1.0000 -0.0004 -1.0004 0.1079 0.1177 -0.1444
-1.0011 -0.9993 2.0012 -0.2002 -0.2188 0.0325
1.0011 0.9993 -2.0012 0.2002 0.2188 -0.0325
-0.0011 -1.0000 -2.0003 -0.1571 0.1150 -0.1018

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0202
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19192
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.455
_diffrn_reflns_theta_min         4.319
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00  22.00   0.50    0.10    --  -49.76  57.00-180.00  116
  2  ω    -42.00  -5.00   0.50    0.10    --  -49.76  38.00 -30.00   74
  3  ω     -2.00  29.00   0.50    0.10    --  -49.76  38.00 -30.00   62
  4  ω    -27.00  19.00   0.50    0.10    --  -49.76  19.00  60.00   92
  5  ω     74.00 100.00   0.50    0.10    --   48.76 125.00 -60.00   52
  6  ω     71.00  96.00   0.50    0.10    --   48.76 129.00 -36.00   50
  7  ω     96.00 121.00   0.50    0.10    --   96.11 129.00 -36.00   50
  8  ω     73.00  98.00   0.50    0.10    --   48.76 141.00 135.00   50
  9  ω    116.00 141.00   0.50    0.10    --   96.11 141.00 135.00   50
 10  ω     94.00 119.00   0.50    0.10    --  108.00 141.00 135.00   50
 11  ω    -30.00  19.00   0.50    0.10    --   48.76 -19.00 120.00   98
 12  ω     19.00  44.00   0.50    0.10    --   96.11 -45.00  30.00   50
 13  ω     43.00  88.00   0.50    0.10    --  108.00 -77.00  60.00   90
 14  ω     51.00  95.00   0.50    0.10    --   96.11 -77.00 -60.00   88
 15  ω     79.00 104.00   0.50    0.10    --  108.00 -77.00-120.00   50
 16  ω     20.00  48.00   0.50    0.10    --   96.11 -45.00-150.00   56
 17  ω     22.00  49.00   0.50    0.10    --   96.11 -45.00 -90.00   54
 18  ω    -27.00  23.00   0.50    0.10    --   48.76 -19.00  60.00  100
 19  ω     66.00 106.00   0.50    0.10    --  108.00 -95.00 120.00   80
 20  ω     43.00  75.00   0.50    0.10    --   96.11-141.00  78.00   64
 21  ω     59.00 124.00   0.50    0.10    --  108.00-141.00  78.00  130
 22  ω     57.00  84.00   0.50    0.10    --   48.76-141.00  78.00   54
 23  ω     36.00 109.00   0.50    0.10    --  108.00-125.00 -60.00  146
 24  ω     51.00  76.00   0.50    0.10    --  108.00-129.00-109.00   50
 25  ω     45.00  70.00   0.50    0.10    --   96.11-129.00-109.00   50
 26  ω     37.00  62.00   0.50    0.10    --   48.76-129.00-109.00   50
 27  ω   -111.00 -77.00   0.50    0.10    --  -92.01 125.00  90.00   68
 28  ω   -123.00 -21.00   0.50    0.10    --  -92.01 141.00 135.00  204
 29  ω    -76.00 -51.00   0.50    0.10    --  -49.76 141.00 135.00   50
 30  ω    -85.00 -60.00   0.50    0.10    --  -49.76 129.00 -36.00   50
 31  ω    -91.00 -66.00   0.50    0.10    --  -92.01 129.00 -36.00   50
 32  ω    -71.00 -24.00   0.50    0.10    --  -92.01  61.00 -60.00   94
 33  ω    -51.00 -14.00   0.50    0.10    --  -92.01  45.00-180.00   74
 34  ω    -49.00 -14.00   0.50    0.10    --  -92.01  45.00   0.00   70
 35  ω    -48.00 -17.00   0.50    0.10    --  -92.01  45.00  90.00   62
 36  ω    -67.00 -17.00   0.50    0.10    --  -92.01  61.00 120.00  100
 37  ω    -50.00 -16.00   0.50    0.10    --  -92.01  45.00 120.00   68
 38  ω   -167.00 -73.00   0.50    0.10    --  -92.01 -30.00  60.00  188
 39  ω   -138.00-113.00   0.50    0.10    --  -92.01-141.00  78.00   50
 40  ω   -116.00 -77.00   0.50    0.10    --  -49.76-125.00 120.00   78
 41  ω   -132.00-107.00   0.50    0.10    --  -92.01 -95.00 120.00   50
 42  ω   -161.00 -75.00   0.50    0.10    --  -92.01-125.00  30.00  172
 43  ω   -129.00 -84.00   0.50    0.10    --  -92.01 -95.00 -60.00   90
 44  ω   -129.00 -86.00   0.50    0.10    --  -92.01-129.00-109.00   86
 45  ω   -121.00 -96.00   0.50    0.10    --  -49.76-129.00-109.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1295545000
_diffrn_orient_matrix_UB_12      0.1137524000
_diffrn_orient_matrix_UB_13      0.0215856000
_diffrn_orient_matrix_UB_21      0.0457156000
_diffrn_orient_matrix_UB_22      0.0289651000
_diffrn_orient_matrix_UB_23      -0.0720173000
_diffrn_orient_matrix_UB_31      -0.1477550000
_diffrn_orient_matrix_UB_32      0.1087015000
_diffrn_orient_matrix_UB_33      -0.0033833000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.701
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.926
_reflns_number_gt                2971
_reflns_number_total             3057
_reflns_odcompleteness_completeness 100.00
_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 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1201 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(5)
_refine_ls_extinction_coef       0.0025(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0252
_refine_ls_restrained_S_all      1.046
_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)+(0.0362P)²+0.1814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0649
_refine_ls_wR_factor_ref         0.0654
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.75556(6) 0.43065(5) 0.55219(2) 0.03631(14) Uani 1 1 d . . . . .
O1 O 0.57558(18) 0.50781(13) 0.71896(6) 0.0323(3) Uani 1 1 d . . . . .
N1 N 0.69028(19) 0.53090(15) 0.61787(7) 0.0262(3) Uani 1 1 d . . . . .
C1 C 0.5731(2) 0.47097(17) 0.66228(9) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.4377(2) 0.37316(17) 0.63691(9) 0.0244(3) Uani 1 1 d . . . . .
C3 C 0.3853(2) 0.26524(19) 0.67815(9) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.441828 0.252059 0.719018 0.034 Uiso 1 1 calc R U . . .
C4 C 0.2506(3) 0.17748(18) 0.65925(9) 0.0323(4) Uani 1 1 d . . . . .
H4 H 0.216600 0.102646 0.686697 0.039 Uiso 1 1 calc R U . . .
C5 C 0.1659(2) 0.1989(2) 0.60049(10) 0.0330(4) Uani 1 1 d . . . . .
H5 H 0.073316 0.138806 0.587711 0.040 Uiso 1 1 calc R U . . .
C6 C 0.2153(2) 0.30769(19) 0.56002(9) 0.0306(4) Uani 1 1 d . . . . .
H6 H 0.155284 0.322946 0.519997 0.037 Uiso 1 1 calc R U . . .
C7 C 0.3518(2) 0.39382(18) 0.57801(9) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.386847 0.467351 0.549977 0.033 Uiso 1 1 calc R U . . .
C8 C 0.8259(2) 0.62078(18) 0.64330(9) 0.0257(4) Uani 1 1 d . . . . .
C9 C 0.8097(2) 0.76635(18) 0.63839(9) 0.0263(4) Uani 1 1 d . . . . .
C10 C 0.9430(2) 0.84170(19) 0.66933(10) 0.0305(4) Uani 1 1 d . . . . .
H10 H 0.936712 0.940230 0.668938 0.037 Uiso 1 1 calc R U . . .
C11 C 1.0836(2) 0.7792(2) 0.70050(9) 0.0336(4) Uani 1 1 d . . . . .
H11 H 1.170361 0.835134 0.720868 0.040 Uiso 1 1 calc R U . . .
C12 C 1.0988(2) 0.6359(2) 0.70219(9) 0.0326(4) Uani 1 1 d . . . . .
H12 H 1.196608 0.592710 0.722433 0.039 Uiso 1 1 calc R U . . .
C13 C 0.9681(2) 0.5574(2) 0.67369(9) 0.0305(4) Uani 1 1 d . . . . .
H13 H 0.975291 0.458955 0.674845 0.037 Uiso 1 1 calc R U . . .
C14 C 0.6626(2) 0.83986(18) 0.60048(9) 0.0277(4) Uani 1 1 d . . . . .
C15 C 0.6678(3) 0.7961(2) 0.52835(9) 0.0363(4) Uani 1 1 d . . . . .
H15A H 0.786207 0.810153 0.511054 0.054 Uiso 1 1 calc R U . . .
H15B H 0.584551 0.852472 0.503363 0.054 Uiso 1 1 calc R U . . .
H15C H 0.636042 0.697842 0.524617 0.054 Uiso 1 1 calc R U . . .
C16 C 0.4805(2) 0.8094(2) 0.62934(10) 0.0319(4) Uani 1 1 d . . . . .
H16A H 0.456308 0.709647 0.626397 0.048 Uiso 1 1 calc R U . . .
H16B H 0.391454 0.860845 0.604769 0.048 Uiso 1 1 calc R U . . .
H16C H 0.477705 0.838320 0.675219 0.048 Uiso 1 1 calc R U . . .
C17 C 0.6839(3) 0.9986(2) 0.60262(11) 0.0403(5) Uani 1 1 d . . . . .
H17A H 0.678818 1.030390 0.648055 0.061 Uiso 1 1 calc R U . . .
H17B H 0.589244 1.042209 0.577604 0.061 Uiso 1 1 calc R U . . .
H17C H 0.797040 1.024393 0.583569 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 N1 1.7288(15) . ?
O1 C1 1.214(2) . ?
N1 C1 1.400(2) . ?
N1 C8 1.446(2) . ?
C1 C2 1.492(2) . ?
C2 C3 1.398(2) . ?
C2 C7 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.411(2) . ?
C8 C13 1.392(3) . ?
C9 C10 1.401(2) . ?
C9 C14 1.537(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.386(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.536(3) . ?
C14 C16 1.539(2) . ?
C14 C17 1.538(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

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 N1 Cl1 117.33(12) . . ?
C1 N1 C8 118.06(15) . . ?
C8 N1 Cl1 114.06(12) . . ?
O1 C1 N1 119.38(15) . . ?
O1 C1 C2 121.89(16) . . ?
N1 C1 C2 118.48(15) . . ?
C3 C2 C1 117.23(16) . . ?
C7 C2 C1 122.68(16) . . ?
C7 C2 C3 119.75(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.82(17) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.97(16) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.35(17) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 119.91(16) . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 119.9 . . ?
C6 C7 C2 120.17(16) . . ?
C6 C7 H7 119.9 . . ?
C9 C8 N1 120.40(16) . . ?
C13 C8 N1 117.18(16) . . ?
C13 C8 C9 122.39(17) . . ?
C8 C9 C14 123.88(15) . . ?
C10 C9 C8 114.75(17) . . ?
C10 C9 C14 121.34(15) . . ?
C9 C10 H10 118.5 . . ?
C11 C10 C9 123.07(17) . . ?
C11 C10 H10 118.5 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.58(18) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 120.8 . . ?
C13 C12 C11 118.31(18) . . ?
C13 C12 H12 120.8 . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.82(17) . . ?
C12 C13 H13 119.6 . . ?
C9 C14 C16 112.23(15) . . ?
C9 C14 C17 111.49(15) . . ?
C15 C14 C9 109.89(15) . . ?
C15 C14 C16 109.88(15) . . ?
C15 C14 C17 107.29(16) . . ?
C17 C14 C16 105.88(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
Cl1 N1 C1 O1 151.03(15) . . . . ?
Cl1 N1 C1 C2 -34.6(2) . . . . ?
Cl1 N1 C8 C9 113.84(16) . . . . ?
Cl1 N1 C8 C13 -67.71(19) . . . . ?
O1 C1 C2 C3 -37.7(3) . . . . ?
O1 C1 C2 C7 135.69(19) . . . . ?
N1 C1 C2 C3 148.13(16) . . . . ?
N1 C1 C2 C7 -38.5(3) . . . . ?
N1 C8 C9 C10 175.26(16) . . . . ?
N1 C8 C9 C14 -6.8(3) . . . . ?
N1 C8 C13 C12 -176.70(16) . . . . ?
C1 N1 C8 C9 -102.3(2) . . . . ?
C1 N1 C8 C13 76.2(2) . . . . ?
C1 C2 C3 C4 175.11(17) . . . . ?
C1 C2 C7 C6 -173.45(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C2 -1.0(3) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C8 N1 C1 O1 8.3(2) . . . . ?
C8 N1 C1 C2 -177.31(15) . . . . ?
C8 C9 C10 C11 2.2(3) . . . . ?
C8 C9 C14 C15 -59.5(2) . . . . ?
C8 C9 C14 C16 63.0(2) . . . . ?
C8 C9 C14 C17 -178.36(17) . . . . ?
C9 C8 C13 C12 1.7(3) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C9 C14 C15 118.31(19) . . . . ?
C10 C9 C14 C16 -119.10(19) . . . . ?
C10 C9 C14 C17 -0.5(2) . . . . ?
C10 C11 C12 C13 -1.8(3) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
C13 C8 C9 C10 -3.1(3) . . . . ?
C13 C8 C9 C14 174.87(16) . . . . ?
C14 C9 C10 C11 -175.87(17) . . . . ?

_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 1.306
_oxdiff_exptl_absorpt_empirical_full_min 0.780
####################################################################### 
# 
# 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_rja230008_fa
_database_code_depnum_ccdc_archive 'CCDC 2307641'
loop_
_audit_author_name
_audit_author_address
'Paul G. Waddell'
;Newcastle University
United Kingdom
;
_audit_update_record             
;
2023-11-13 deposited with the CCDC.	2024-03-08 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_chemical_formula_moiety         'C13 H18 Cl N O'
_chemical_formula_sum            'C13 H18 Cl N O'
_chemical_formula_weight         239.746
_chemical_oxdiff_formula         'C13 H18 Cl1 N1 O1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   6.66649(19)
_cell_length_b                   9.4285(3)
_cell_length_c                   10.2117(3)
_cell_angle_alpha                93.580(2)
_cell_angle_beta                 96.362(2)
_cell_angle_gamma                93.083(2)
_cell_volume                     635.47(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7636
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      75.8840
_cell_measurement_theta_min      4.3590
_exptl_absorpt_coefficient_mu    2.486
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             257.434
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0112
0 0 -1 0.0462
0 -1 0 0.0760
1 0 0 0.0865
-1 0 0 0.0835
0 1 0 0.1070
1 1 0 0.0851
1 -1 0 0.1049
0 -1 1 0.0495
0 1 -1 0.0905
1 2 0 0.0867

_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
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
-0.0000 0.0000 1.0000 0.1171 -0.0954 0.0182
0.0000 -0.0000 -1.0000 -0.1171 0.0954 -0.0182
-0.0000 -1.0000 0.0000 0.0497 0.0509 -0.1478
1.0000 0.0000 -0.0000 0.1384 0.1490 0.1136
-1.0000 -0.0000 0.0000 -0.1384 -0.1490 -0.1136
0.0000 1.0000 -0.0000 -0.0497 -0.0509 0.1478
1.0000 1.0000 -0.0000 0.0887 0.0982 0.2614
1.0000 -1.0000 0.0000 0.1881 0.1999 -0.0342
-0.0000 -1.0000 1.0000 0.1668 -0.0445 -0.1296
0.0000 1.0000 -1.0000 -0.1668 0.0445 0.1296
1.0000 2.0000 -0.0000 0.0390 0.0473 0.4092

_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0219
_diffrn_reflns_Laue_measured_fraction_full 0.9987
_diffrn_reflns_Laue_measured_fraction_max 0.9295
_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       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13900
_diffrn_reflns_point_group_measured_fraction_full 0.9987
_diffrn_reflns_point_group_measured_fraction_max 0.9295
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.60
_diffrn_reflns_theta_min         4.37
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.9295
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00  90.00   0.50    0.05    --   48.76 156.00 -20.00   64
  2  ω      0.00  25.00   0.50    0.05    --   38.00  97.00  91.24   50
  3  ω    -44.00 -14.00   0.50    0.05    --   10.00 128.00  93.35   60
  4  ω    -33.00  -8.00   0.50    0.05    --   14.00 116.00  24.95   50
  5  ω     15.00  40.00   0.50    0.05    --   50.00  91.00 118.39   50
  6  ω     15.00  40.00   0.50    0.05    --   50.00  92.00  57.26   50
  7  ω    -26.00  -1.00   0.50    0.05    --   18.00 108.00-135.02   50
  8  ω      8.00  37.00   0.50    0.05    --   42.00  90.00-100.38   58
  9  ω     16.00  41.00   0.50    0.05    --   50.00  90.00-114.30   50
 10  ω     24.00  90.00   0.50    0.05    --   48.76  77.00   0.00  132
 11  ω     44.00  69.00   0.50    0.05    --   70.00  76.00-108.70   50
 12  ω     70.00 113.00   0.50    0.05    --   96.11  77.00  30.00   86
 13  ω     33.00  60.00   0.50    0.05    --   58.00  76.00  91.53   54
 14  ω     33.00  59.00   0.50    0.05    --   58.00  75.00 147.44   52
 15  ω     32.00  70.00   0.50    0.05    --   54.00  77.00 174.11   76
 16  ω     87.00 112.00   0.50    0.05    --   54.00  77.00 174.11   50
 17  ω     82.00 107.00   0.50    0.05    --   96.11 156.00 -20.00   50
 18  ω    103.00 128.00   0.50    0.05    --  108.00 120.00-176.00   50
 19  ω     21.00  49.00   0.50    0.05    --   96.11 -45.00-180.00   56
 20  ω     35.00  67.00   0.50    0.05    --  108.00 -61.00-120.00   64
 21  ω     19.00  51.00   0.50    0.05    --   96.11 -45.00 -30.00   64
 22  ω     34.00  69.00   0.50    0.05    --  108.00 -61.00 120.00   70
 23  ω     39.00 106.00   0.50    0.05    --  108.00 -95.00 120.00  134
 24  ω     70.00 109.00   0.50    0.05    --  108.00-120.00  99.00   78
 25  ω     28.00 105.00   0.50    0.05    --   96.11 -95.00 -30.00  154
 26  ω     43.00  95.00   0.50    0.05    --  108.00 -95.00 -90.00  104
 27  ω     62.00  87.00   0.50    0.05    --  108.00-156.00 -57.00   50
 28  ω     57.00  82.00   0.50    0.05    --   96.11-156.00 -57.00   50
 29  ω     53.00  78.00   0.50    0.05    --   48.76-156.00 -57.00   50
 30  ω     50.00  96.00   0.50    0.05    --   48.76-120.00  99.00   92
 31  ω     17.00  47.00   0.50    0.05    --   48.76-120.00  99.00   60
 32  ω   -130.00-105.00   0.50    0.05    --  -92.01-156.00 -57.00   50
 33  ω    -83.00 -53.00   0.50    0.05    --  -49.76-156.00 -57.00   60
 34  ω   -121.00 -96.00   0.50    0.05    --  -92.01-120.00  99.00   50
 35  ω   -152.00-126.00   0.50    0.05    --  -92.01 -61.00   0.00   52
 36  ω    -93.00 -65.00   0.50    0.05    --  -92.01 -77.00-150.00   56
 37  ω    -53.00 -26.00   0.50    0.05    --  -49.76 -77.00-120.00   54
 38  ω    -49.00 -23.00   0.50    0.05    --  -49.76 -77.00 -60.00   52
 39  ω   -146.00-103.00   0.50    0.05    --  -92.01 -77.00-150.00   86
 40  ω   -109.00 -68.00   0.50    0.05    --  -92.01 -77.00 -90.00   82
 41  ω   -141.00 -70.00   0.50    0.05    --  -92.01 -77.00  90.00  142
 42  ω   -156.00 -65.00   0.50    0.05    --  -92.01 -77.00 120.00  182
 43  ω    -60.00 -35.00   0.50    0.05    --  -62.00 -77.00 154.17   50
 44  ω    -73.00 -48.00   0.50    0.05    --  -74.00 -76.00 118.28   50
 45  ω   -114.00 -88.00   0.50    0.05    --  -62.00 -77.00 154.17   52
 46  ω    -69.00 -44.00   0.50    0.05    --  -70.00 -76.00  33.99   50
 47  ω    -89.00 -53.00   0.50    0.05    --  -78.00 -76.00 -44.95   72
 48  ω    -74.00 -48.00   0.50    0.05    --  -74.00 -76.00 -87.50   52
 49  ω   -145.00 -99.00   0.50    0.05    --  -78.00 -76.00 -44.95   92
 50  ω   -148.00-112.00   0.50    0.05    --  -92.01 -77.00 -90.00   72
 51  ω    -70.00 -45.00   0.50    0.05    --  -70.00 -74.00-176.61   50
 52  ω    -63.00 -37.00   0.50    0.05    --  -62.00 -73.00 -92.56   52
 53  ω    -79.00 -52.00   0.50    0.05    --  -78.00 -75.00  13.71   54
 54  ω   -100.00 -65.00   0.50    0.05    --  -90.00 -73.00 -45.61   70
 55  ω   -145.00-106.00   0.50    0.05    --  -78.00 -75.00  13.71   78
 56  ω   -158.00-118.00   0.50    0.05    --  -90.00 -73.00 -45.61   80
 57  ω   -163.00-137.00   0.50    0.05    --  -99.00 -73.00-155.54   52
 58  ω   -102.00 -74.00   0.50    0.05    --  -99.00 -73.00-155.54   56
 59  ω    -73.00 -47.00   0.50    0.05    --  -70.00 -72.00 -31.01   52
 60  ω   -113.00 -75.00   0.50    0.05    --  -99.00 -71.00 -72.31   76
 61  ω   -154.00-116.00   0.50    0.05    --  -90.00 -71.00 -25.17   76
 62  ω   -166.00-126.00   0.50    0.05    --  -99.00 -71.00 -72.31   80
 63  ω   -103.00 -66.00   0.50    0.05    --  -90.00 -71.00 -25.17   74
 64  ω   -145.00 -76.00   0.50    0.05    --  -99.00 -70.00-131.59  138
 65  ω    -96.00 -54.00   0.50    0.05    --  -78.00 -71.00  59.40   84
 66  ω    -88.00 -55.00   0.50    0.05    --  -78.00 -69.00  71.80   66
 67  ω    -93.00 -57.00   0.50    0.05    --  -78.00 -70.00  99.66   72
 68  ω    -95.00 -66.00   0.50    0.05    --  -90.00 -71.00 132.93   58
 69  ω    -77.00 -51.00   0.50    0.05    --  -74.00 -69.00 167.34   52
 70  ω   -161.00 -69.00   0.50    0.05    --  -90.00 -67.00 168.96  184
 71  ω   -158.00 -64.00   0.50    0.05    --  -86.00 -69.00  31.60  188
 72  ω    -94.00 -65.00   0.50    0.05    --  -86.00 -63.00 139.73   58
 73  ω   -156.00-112.00   0.50    0.05    --  -86.00 -63.00 139.73   88
 74  ω    -92.00 -67.00   0.50    0.05    --  -90.00 -69.00  48.86   50
 75  ω    -94.00 -69.00   0.50    0.05    --  -90.00 -66.00 -11.62   50
 76  ω    -98.00 -73.00   0.50    0.05    --  -92.01 -61.00   0.00   50
 77  ω    -88.00 -62.00   0.50    0.05    --  -82.00 -66.00-128.43   52
 78  ω   -100.00 -67.00   0.50    0.05    --  -92.01  77.00-180.00   66
 79  ω    -63.00 -36.00   0.50    0.05    --  -92.01  77.00-180.00   54
 80  ω   -100.00 -50.00   0.50    0.05    --  -92.01 120.00-176.00  100
 81  ω    -68.00 -42.00   0.50    0.05    --  -49.76 120.00-176.00   52
 82  ω    -89.00 -64.00   0.50    0.05    --  -92.01 156.00 -20.00   50
 83  ω    -62.00 -24.00   0.50    0.05    --  -92.01  77.00  30.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1383649000
_diffrn_orient_matrix_UB_12      -0.0496893000
_diffrn_orient_matrix_UB_13      0.1171478000
_diffrn_orient_matrix_UB_21      0.1490456000
_diffrn_orient_matrix_UB_22      -0.0508641000
_diffrn_orient_matrix_UB_23      -0.0953809000
_diffrn_orient_matrix_UB_31      0.1136246000
_diffrn_orient_matrix_UB_32      0.1478062000
_diffrn_orient_matrix_UB_33      0.0181983000
_diffrn_oxdiff_digest_frames     
;
0100b4ee7ff8f213440eb12b4ed1310cce05902c7be
;
_diffrn_oxdiff_digest_hkl        
;
01de8c1636134dc45f8b1aeeae182e5593917a
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184

_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              11
_reflns_limit_k_min              -11
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                2334
_reflns_number_total             2505
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.2271
_refine_diff_density_min         -0.2115
_refine_diff_density_rms         0.0370
_refine_ls_d_res_high            0.7893
_refine_ls_d_res_low             10.1247
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0393
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    27
_refine_ls_number_parameters     150
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.0393
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0397P)²+0.1645P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0812
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C3(H3a,H3b,H3c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl1 Cl -0.26171(4) 0.76762(4) 0.81072(3) 0.03805(13) Uani 1.000000 .
O1 O -0.05049(14) 0.84249(10) 1.06388(9) 0.0339(2) Uani 1.000000 .
N1 N -0.00357(15) 0.77150(12) 0.85334(11) 0.0290(2) Uani 1.000000 .
C1 C 0.06419(18) 0.82666(13) 0.98024(12) 0.0270(3) Uani 1.000000 .
C9 C 0.1269(2) 0.91309(15) 0.68977(13) 0.0338(3) Uani 1.000000 .
H9 H 0.0616(2) 0.99058(15) 0.72685(13) 0.0405(4) Uiso 1.000000 R
C6 C 0.3160(2) 0.68724(15) 0.58574(13) 0.0329(3) Uani 1.000000 .
H6 H 0.3850(2) 0.61130(15) 0.54937(13) 0.0395(4) Uiso 1.000000 R
C2 C 0.28985(19) 0.86436(14) 1.00611(13) 0.0299(3) Uani 1.000000 .
H2a H 0.36067(19) 0.80310(14) 0.94619(13) 0.0359(3) Uiso 1.000000 R
H2b H 0.31706(19) 0.96448(14) 0.98600(13) 0.0359(3) Uiso 1.000000 R
C5 C 0.20200(18) 0.66113(13) 0.68992(12) 0.0264(3) Uani 1.000000 .
C12 C 0.2840(2) 0.50618(15) 0.88167(13) 0.0364(3) Uani 1.000000 .
H12a H 0.4254(5) 0.5423(10) 0.8862(3) 0.0546(5) Uiso 1.000000 GR
H12b H 0.2135(10) 0.5657(9) 0.94168(19) 0.0546(5) Uiso 1.000000 GR
H12c H 0.2785(14) 0.4079(2) 0.9077(4) 0.0546(5) Uiso 1.000000 GR
C4 C 0.11181(18) 0.78057(14) 0.74174(12) 0.0271(3) Uani 1.000000 .
C7 C 0.3327(2) 0.81908(16) 0.53323(13) 0.0376(3) Uani 1.000000 .
H7 H 0.4107(2) 0.83124(16) 0.46186(13) 0.0452(4) Uiso 1.000000 R
C3 C 0.3736(2) 0.84575(16) 1.14814(14) 0.0385(3) Uani 1.000000 .
H3a H 0.5168(5) 0.8787(11) 1.1621(3) 0.0577(5) Uiso 1.000000 GR
H3b H 0.2983(11) 0.9016(9) 1.20809(14) 0.0577(5) Uiso 1.000000 GR
H3c H 0.3597(15) 0.7449(2) 1.1658(3) 0.0577(5) Uiso 1.000000 GR
C10 C 0.18154(19) 0.51045(14) 0.74007(12) 0.0295(3) Uani 1.000000 .
C11 C 0.2821(3) 0.40145(17) 0.65410(16) 0.0490(4) Uani 1.000000 .
H11a H 0.2220(13) 0.4017(10) 0.5621(3) 0.0736(6) Uiso 1.000000 GR
H11b H 0.4274(4) 0.4269(8) 0.6599(10) 0.0736(6) Uiso 1.000000 GR
H11c H 0.2608(17) 0.3063(3) 0.6856(8) 0.0736(6) Uiso 1.000000 GR
C8 C 0.2367(2) 0.93246(16) 0.58409(14) 0.0380(3) Uani 1.000000 .
H8 H 0.2457(2) 1.02236(16) 0.54731(14) 0.0456(4) Uiso 1.000000 R
C13 C -0.0415(2) 0.45855(15) 0.73510(16) 0.0409(3) Uani 1.000000 .
H13a H -0.1049(5) 0.5139(8) 0.8020(7) 0.0613(5) Uiso 1.000000 GR
H13b H -0.1115(4) 0.4711(11) 0.6474(4) 0.0613(5) Uiso 1.000000 GR
H13c H -0.0506(2) 0.3576(3) 0.7527(11) 0.0613(5) Uiso 1.000000 GR


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 N1 1.7255(10) . ?
O1 C1 1.2154(15) . ?
N1 C1 1.3838(17) . ?
N1 C4 1.4481(15) . ?
C1 C2 1.5172(17) . ?
C9 H9 0.9500 . ?
C9 C4 1.3907(18) . ?
C9 C8 1.3854(19) . ?
C6 H6 0.9500 . ?
C6 C5 1.4007(17) . ?
C6 C7 1.388(2) . ?
C2 H2a 0.9900 . ?
C2 H2b 0.9900 . ?
C2 C3 1.5196(18) . ?
C5 C4 1.4066(17) . ?
C5 C10 1.5443(17) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C12 C10 1.5330(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.378(2) . ?
C3 H3a 0.9800 . ?
C3 H3b 0.9800 . ?
C3 H3c 0.9800 . ?
C10 C11 1.5389(19) . ?
C10 C13 1.5346(19) . ?
C11 H11a 0.9800 . ?
C11 H11b 0.9800 . ?
C11 H11c 0.9800 . ?
C8 H8 0.9500 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?

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 N1 Cl1 115.43(8) . . ?
C4 N1 Cl1 113.64(8) . . ?
C4 N1 C1 124.39(10) . . ?
N1 C1 O1 121.71(11) . . ?
C2 C1 O1 123.22(11) . . ?
C2 C1 N1 115.06(10) . . ?
C4 C9 H9 119.90(8) . . ?
C8 C9 H9 119.90(8) . . ?
C8 C9 C4 120.21(13) . . ?
C5 C6 H6 118.52(8) . . ?
C7 C6 H6 118.52(8) . . ?
C7 C6 C5 122.96(13) . . ?
H2a C2 C1 109.13(7) . . ?
H2b C2 C1 109.13(7) . . ?
H2b C2 H2a 107.9 . . ?
C3 C2 C1 112.35(11) . . ?
C3 C2 H2a 109.13(8) . . ?
C3 C2 H2b 109.13(7) . . ?
C4 C5 C6 114.90(12) . . ?
C10 C5 C6 120.57(11) . . ?
C10 C5 C4 124.53(11) . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
C10 C12 H12a 109.5 . . ?
C10 C12 H12b 109.5 . . ?
C10 C12 H12c 109.5 . . ?
C9 C4 N1 116.11(11) . . ?
C5 C4 N1 121.25(11) . . ?
C5 C4 C9 122.64(12) . . ?
H7 C7 C6 119.83(8) . . ?
C8 C7 C6 120.34(13) . . ?
C8 C7 H7 119.83(8) . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
C12 C10 C5 111.54(10) . . ?
C11 C10 C5 111.38(11) . . ?
C11 C10 C12 106.79(11) . . ?
C13 C10 C5 111.01(10) . . ?
C13 C10 C12 109.06(11) . . ?
C13 C10 C11 106.86(12) . . ?
H11a C11 C10 109.5 . . ?
H11b C11 C10 109.5 . . ?
H11b C11 H11a 109.5 . . ?
H11c C11 C10 109.5 . . ?
H11c C11 H11a 109.5 . . ?
H11c C11 H11b 109.5 . . ?
C7 C8 C9 118.88(13) . . ?
H8 C8 C9 120.56(8) . . ?
H8 C8 C7 120.56(8) . . ?
H13a C13 C10 109.5 . . ?
H13b C13 C10 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C10 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?

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
Cl1 N1 C1 O1 15.03(10) . . . . ?
Cl1 N1 C1 C2 -165.29(9) . . . . ?
Cl1 N1 C4 C9 75.68(10) . . . . ?
Cl1 N1 C4 C5 -104.16(9) . . . . ?
O1 C1 N1 C4 164.73(11) . . . . ?
O1 C1 C2 C3 31.01(14) . . . . ?
N1 C1 C2 C3 -148.67(11) . . . . ?
N1 C4 C9 C8 179.08(11) . . . . ?
N1 C4 C5 C6 -177.38(11) . . . . ?
N1 C4 C5 C10 2.73(14) . . . . ?
C9 C4 C5 C6 2.79(14) . . . . ?
C9 C4 C5 C10 -177.10(11) . . . . ?
C9 C8 C7 C6 1.19(16) . . . . ?
C6 C5 C10 C12 114.09(12) . . . . ?
C6 C5 C10 C11 -5.12(14) . . . . ?
C6 C5 C10 C13 -124.06(13) . . . . ?

_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.671
