# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_2021acc0021_d2_100k
_database_code_depnum_ccdc_archive 'CCDC 2143446'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 F N O'
_chemical_formula_sum            'C23 H16 F N O'
_chemical_formula_weight         341.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N1 O1 F1'
_chemical_oxdiff_usercomment     'RAK-408 MeOH'
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'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   12.4459(2)
_cell_length_b                   27.6090(4)
_cell_length_c                   4.77340(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1640.23(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.5980
_cell_measurement_theta_min      3.8700
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             712
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0142
0 0 -1 0.0142
-2 3 -1 0.1279
2 -3 1 0.1279
5 0 2 0.0203
-5 0 -2 0.0203

_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.05
_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
-0.0001 -0.0003 0.9999 -0.0316 0.0436 0.0147
0.0001 0.0003 -0.9999 0.0316 -0.0436 -0.0147
-2.0038 2.9974 -1.0002 -0.0962 0.1867 -0.9781
2.0038 -2.9974 1.0002 0.0962 -0.1867 0.9781
4.9963 0.0028 2.0071 0.4444 0.3993 0.1948
-4.9963 -0.0028 -2.0071 -0.4444 -0.3993 -0.1948

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15030
_diffrn_reflns_point_group_measured_fraction_full 0.893
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.759
_diffrn_reflns_theta_min         3.201
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00 120.00   0.50    0.26    --   45.19  38.00-120.00  162
  2  ω    104.00 133.00   0.50    1.04    --  109.75  15.00  60.00   58
  3  ω    104.00 162.00   0.50    1.04    --  109.75  29.00 158.00  116
  4  ω    104.00 133.00   0.50    1.04    --  109.75  15.00 150.00   58
  5  ω     40.00 123.00   0.50    0.26    --   45.19  29.00 158.00  166
  6  ω    104.00 133.00   0.50    1.04    --  109.75  15.00  30.00   58
  7  ω    104.00 133.00   0.50    1.04    --  109.75  15.00 -60.00   58
  8  ω    104.00 133.00   0.50    1.04    --  109.75  15.00-120.00   58
  9  ω     -7.00  32.00   0.50    0.26    --  -45.19  29.00 158.00   78
 10  ω    -22.00  30.00   0.50    0.26    --  -45.19  38.00  30.00  104
 11  ω    -78.00 -23.00   0.50    1.04    --  -97.00  77.00 -90.00  110
 12  ω    -54.00 -23.00   0.50    1.04    --  -97.00  61.00-150.00   62
 13  ω    -54.00 -23.00   0.50    1.04    --  -97.00  61.00 -90.00   62
 14  ω    -54.00 -23.00   0.50    1.04    --  -97.00  61.00   0.00   62
 15  ω    -94.00 -23.00   0.50    1.04    --  -97.00 105.00  -3.00  142
 16  ω   -170.00-106.00   0.50    1.04    --  -97.00-104.00 161.00  128
 17  ω   -120.00 -39.00   0.50    0.26    --  -45.19 -38.00  60.00  162
 18  ω   -120.00 -39.00   0.50    0.26    --  -45.19 -38.00   0.00  162
 19  ω   -169.00 -90.00   0.50    1.04    --  -97.00 -30.00 -60.00  158
 20  ω   -120.00 -39.00   0.50    0.26    --  -45.19 -38.00 -60.00  162
 21  ω    -30.00  16.00   0.50    0.26    --   45.19 -38.00-120.00   92
 22  ω    -30.00  16.00   0.50    0.26    --   45.19 -38.00-180.00   92
 23  ω    -31.00   1.00   0.50    0.26    --   45.19 -29.00  -2.00   64
 24  ω    -30.00  16.00   0.50    0.26    --   45.19 -38.00  60.00   92
 25  ω     37.00  72.00   0.50    1.04    --  109.75 -77.00  90.00   70
 26  ω     37.00  72.00   0.50    1.04    --  109.75 -77.00  60.00   70
 27  ω     -3.00  79.00   0.50    0.26    --   45.19-104.00 161.00  164
 28  ω     37.00  93.00   0.50    1.04    --  109.75 -95.00 -30.00  112
 29  ω     37.00  94.00   0.50    1.04    --  109.75-105.00-104.00  114
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1016146000
_diffrn_orient_matrix_UB_12      0.0253170000
_diffrn_orient_matrix_UB_13      -0.0315529000
_diffrn_orient_matrix_UB_21      0.0623359000
_diffrn_orient_matrix_UB_22      0.1185244000
_diffrn_orient_matrix_UB_23      0.0436285000
_diffrn_orient_matrix_UB_31      0.0332784000
_diffrn_orient_matrix_UB_32      -0.2991889000
_diffrn_orient_matrix_UB_33      0.0146234000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.550
_reflns_Friedel_fraction_full    0.753
_reflns_Friedel_fraction_max     0.689
_reflns_number_gt                2791
_reflns_number_total             2914
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 960 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0299
_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)+(0.0477P)²+0.2442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0786
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C22(H22), C23(H23)
;
_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
F1 F 0.31484(10) 0.51449(4) -0.5520(3) 0.0348(3) Uani 1 1 d . . . . .
O1 O 0.57382(9) 0.84578(4) 0.8792(3) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.25465(11) 0.87238(6) 1.0611(4) 0.0241(4) Uani 1 1 d . . . . .
C1 C 0.44480(14) 0.89279(6) 1.1571(4) 0.0189(4) Uani 1 1 d . . . . .
C2 C 0.51908(14) 0.92056(6) 1.3116(4) 0.0203(4) Uani 1 1 d . . . . .
H2 H 0.594000 0.916619 1.281142 0.024 Uiso 1 1 calc R U . . .
C3 C 0.48289(15) 0.95326(6) 1.5060(4) 0.0232(4) Uani 1 1 d . . . . .
H3 H 0.532915 0.971798 1.611302 0.028 Uiso 1 1 calc R U . . .
C4 C 0.37138(16) 0.95954(6) 1.5504(5) 0.0251(4) Uani 1 1 d . . . . .
H4 H 0.347107 0.982489 1.684446 0.030 Uiso 1 1 calc R U . . .
C5 C 0.29820(15) 0.93293(7) 1.4025(4) 0.0247(4) Uani 1 1 d . . . . .
H5 H 0.223614 0.937585 1.435166 0.030 Uiso 1 1 calc R U . . .
C6 C 0.33206(14) 0.89861(6) 1.2016(4) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.28598(14) 0.84093(7) 0.8710(5) 0.0225(4) Uani 1 1 d . . . . .
H7 H 0.232631 0.823346 0.771362 0.027 Uiso 1 1 calc R U . . .
C8 C 0.39493(14) 0.83203(6) 0.8077(4) 0.0185(4) Uani 1 1 d . . . . .
C9 C 0.47105(13) 0.85808(6) 0.9540(4) 0.0175(4) Uani 1 1 d . . . . .
C10 C 0.56227(14) 0.81008(6) 0.6767(4) 0.0187(4) Uani 1 1 d . . . . .
C11 C 0.45394(14) 0.80016(6) 0.6236(4) 0.0175(4) Uani 1 1 d . . . . .
C12 C 0.42832(14) 0.76520(6) 0.4239(4) 0.0188(4) Uani 1 1 d . . . . .
H12 H 0.355232 0.758370 0.382292 0.023 Uiso 1 1 calc R U . . .
C13 C 0.50936(14) 0.74040(6) 0.2858(4) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.61739(15) 0.75145(6) 0.3477(4) 0.0228(4) Uani 1 1 d . . . . .
H14 H 0.672702 0.734322 0.252820 0.027 Uiso 1 1 calc R U . . .
C15 C 0.64567(14) 0.78664(6) 0.5433(4) 0.0233(4) Uani 1 1 d . . . . .
H15 H 0.718630 0.794107 0.582818 0.028 Uiso 1 1 calc R U . . .
C16 C 0.48161(15) 0.70087(6) 0.0809(4) 0.0215(4) Uani 1 1 d . . . . .
H16A H 0.537944 0.699225 -0.065177 0.026 Uiso 1 1 calc R U . . .
H16B H 0.412770 0.708864 -0.012120 0.026 Uiso 1 1 calc R U . . .
C17 C 0.47167(14) 0.65114(6) 0.2237(4) 0.0212(4) Uani 1 1 d . . . . .
H17A H 0.542893 0.641074 0.295418 0.025 Uiso 1 1 calc R U . . .
H17B H 0.422079 0.653690 0.385221 0.025 Uiso 1 1 calc R U . . .
C18 C 0.43024(14) 0.61334(6) 0.0224(4) 0.0198(4) Uani 1 1 d . . . . .
C19 C 0.49989(14) 0.58180(6) -0.1152(5) 0.0213(4) Uani 1 1 d . . . . .
H19 H 0.574650 0.583155 -0.075826 0.026 Uiso 1 1 calc R U . . .
C20 C 0.46183(15) 0.54837(6) -0.3092(5) 0.0239(4) Uani 1 1 d . . . . .
H20 H 0.509636 0.527020 -0.403209 0.029 Uiso 1 1 calc R U . . .
C21 C 0.35304(16) 0.54700(7) -0.3617(5) 0.0248(4) Uani 1 1 d . . . . .
C22 C 0.28119(15) 0.57739(7) -0.2303(5) 0.0262(4) Uani 1 1 d . . . . .
H22 H 0.206539 0.575719 -0.270725 0.031 Uiso 1 1 calc R U . . .
C23 C 0.32068(15) 0.61052(6) -0.0372(5) 0.0233(4) Uani 1 1 d . . . . .
H23 H 0.272207 0.631662 0.056011 0.028 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
F1 C21 1.363(2) . ?
O1 C9 1.371(2) . ?
O1 C10 1.388(2) . ?
N1 C6 1.379(2) . ?
N1 C7 1.315(3) . ?
C1 C2 1.409(3) . ?
C1 C6 1.428(2) . ?
C1 C9 1.402(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.415(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.411(2) . ?
C8 C9 1.379(3) . ?
C8 C11 1.444(3) . ?
C10 C11 1.399(2) . ?
C10 C15 1.379(3) . ?
C11 C12 1.394(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.386(3) . ?
C13 C14 1.410(2) . ?
C13 C16 1.506(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.393(3) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.538(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.509(3) . ?
C18 C19 1.393(3) . ?
C18 C23 1.395(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.391(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(3) . ?
C21 C22 1.377(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(3) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 105.11(13) . . ?
C7 N1 C6 118.37(16) . . ?
C2 C1 C6 120.36(17) . . ?
C9 C1 C2 125.51(17) . . ?
C9 C1 C6 114.13(16) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.80(17) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.30(19) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.71(18) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.82(17) . . ?
C6 C5 H5 119.6 . . ?
N1 C6 C1 123.70(17) . . ?
N1 C6 C5 118.29(16) . . ?
C5 C6 C1 118.01(17) . . ?
N1 C7 H7 118.4 . . ?
N1 C7 C8 123.21(18) . . ?
C8 C7 H7 118.4 . . ?
C7 C8 C11 136.49(17) . . ?
C9 C8 C7 117.45(18) . . ?
C9 C8 C11 106.04(15) . . ?
O1 C9 C1 124.54(16) . . ?
O1 C9 C8 112.33(16) . . ?
C8 C9 C1 123.13(16) . . ?
O1 C10 C11 111.42(15) . . ?
C15 C10 O1 125.23(16) . . ?
C15 C10 C11 123.36(17) . . ?
C10 C11 C8 105.10(16) . . ?
C12 C11 C8 136.21(16) . . ?
C12 C11 C10 118.69(16) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.07(16) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 C14 119.17(17) . . ?
C12 C13 C16 120.01(16) . . ?
C14 C13 C16 120.77(16) . . ?
C13 C14 H14 118.9 . . ?
C15 C14 C13 122.17(17) . . ?
C15 C14 H14 118.9 . . ?
C10 C15 C14 116.53(17) . . ?
C10 C15 H15 121.7 . . ?
C14 C15 H15 121.7 . . ?
C13 C16 H16A 109.2 . . ?
C13 C16 H16B 109.2 . . ?
C13 C16 C17 112.20(16) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.26(16) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C19 C18 C17 121.31(16) . . ?
C19 C18 C23 118.49(18) . . ?
C23 C18 C17 120.16(17) . . ?
C18 C19 H19 119.4 . . ?
C20 C19 C18 121.13(17) . . ?
C20 C19 H19 119.4 . . ?
C19 C20 H20 120.9 . . ?
C21 C20 C19 118.29(18) . . ?
C21 C20 H20 120.9 . . ?
F1 C21 C20 118.82(18) . . ?
F1 C21 C22 118.58(17) . . ?
C22 C21 C20 122.60(18) . . ?
C21 C22 H22 120.9 . . ?
C21 C22 C23 118.28(17) . . ?
C23 C22 H22 120.9 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.21(18) . . ?
C22 C23 H23 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C21 C22 C23 -179.80(18) . . . . ?
O1 C10 C11 C8 -0.2(2) . . . . ?
O1 C10 C11 C12 179.69(15) . . . . ?
O1 C10 C15 C14 179.40(17) . . . . ?
N1 C7 C8 C9 -0.2(3) . . . . ?
N1 C7 C8 C11 177.9(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C2 C1 C6 N1 -179.20(17) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C9 O1 0.9(3) . . . . ?
C2 C1 C9 C8 -179.69(17) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 N1 179.22(17) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C6 N1 C7 C8 1.3(3) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C9 O1 -178.93(15) . . . . ?
C6 C1 C9 C8 0.5(3) . . . . ?
C7 N1 C6 C1 -1.5(3) . . . . ?
C7 N1 C6 C5 178.99(18) . . . . ?
C7 C8 C9 O1 178.80(16) . . . . ?
C7 C8 C9 C1 -0.7(3) . . . . ?
C7 C8 C11 C10 -178.2(2) . . . . ?
C7 C8 C11 C12 1.9(4) . . . . ?
C8 C11 C12 C13 -179.0(2) . . . . ?
C9 O1 C10 C11 0.27(19) . . . . ?
C9 O1 C10 C15 -179.34(18) . . . . ?
C9 C1 C2 C3 -179.67(18) . . . . ?
C9 C1 C6 N1 0.6(3) . . . . ?
C9 C1 C6 C5 -179.89(17) . . . . ?
C9 C8 C11 C10 0.0(2) . . . . ?
C9 C8 C11 C12 -179.8(2) . . . . ?
C10 O1 C9 C1 179.25(17) . . . . ?
C10 O1 C9 C8 -0.26(19) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C11 C8 C9 O1 0.2(2) . . . . ?
C11 C8 C9 C1 -179.36(16) . . . . ?
C11 C10 C15 C14 -0.2(3) . . . . ?
C11 C12 C13 C14 -0.8(3) . . . . ?
C11 C12 C13 C16 176.86(17) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C12 C13 C16 C17 -88.8(2) . . . . ?
C13 C14 C15 C10 0.6(3) . . . . ?
C13 C16 C17 C18 172.80(15) . . . . ?
C14 C13 C16 C17 88.8(2) . . . . ?
C15 C10 C11 C8 179.44(18) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C16 C13 C14 C15 -177.73(18) . . . . ?
C16 C17 C18 C19 98.0(2) . . . . ?
C16 C17 C18 C23 -79.7(2) . . . . ?
C17 C18 C19 C20 -177.31(18) . . . . ?
C17 C18 C23 C22 177.33(18) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
C19 C18 C23 C22 -0.4(3) . . . . ?
C19 C20 C21 F1 179.79(17) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C20 C21 C22 C23 -0.2(3) . . . . ?
C21 C22 C23 C18 0.3(3) . . . . ?
C23 C18 C19 C20 0.4(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id 'RAK-408 MeOH'
_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 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.861
####################################################################### 
# 
# 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_2021acc0020_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2143462'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-01-20 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-01-20
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.12.21 svn.raa29eb21 for OlexSys, GUI svn.r6440)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H17 N O'
_chemical_formula_sum            'C23 H17 N O'
_chemical_formula_weight         323.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N1 O1'
_chemical_oxdiff_usercomment     'RAK-398 MeOH'
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'
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                   4.80750(10)
_cell_length_b                   27.2149(4)
_cell_length_c                   12.4496(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.5230(10)
_cell_angle_gamma                90
_cell_volume                     1627.27(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8715
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1850
_cell_measurement_theta_min      3.8870
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.864
_exptl_absorpt_coefficient_mu    0.628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             680
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 5 0.0097
0 1 -5 0.0097
2 5 0 0.0992
-2 -5 0 0.0992
0 -1 0 0.0261
0 1 0 0.0261

_exptl_crystal_recrystallization_method 
'The material was recrystallised from methanol by slow evaporation'
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.05
_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
-0.0043 -0.9862 4.9968 0.1207 0.6096 -0.0079
0.0043 0.9862 -4.9968 -0.1207 -0.6096 0.0079
1.9985 5.0008 0.0078 0.0553 -0.0177 -0.6984
-1.9985 -5.0008 -0.0078 -0.0553 0.0177 0.6984
0.0000 -0.9995 0.0002 0.0496 -0.0043 0.0270
-0.0000 0.9995 -0.0002 -0.0496 0.0043 -0.0270

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15653
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.365
_diffrn_reflns_theta_min         3.248
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  11.00   0.50    0.76    --  -45.19  84.00-124.00  158
  2  ω    -17.00  68.00   0.50    0.76    --   45.19 -84.00 115.00  170
  3  ω    -91.00 -23.00   0.50    3.03    --  -97.00  84.00-124.00  136
  4  ω   -170.00-106.00   0.50    3.03    --  -97.00 -84.00 115.00  128
  5  ω     99.00 175.00   0.50    3.03    --  109.75  84.00-124.00  152
  6  ω     37.00  85.00   0.50    3.03    --  109.75 -84.00 115.00   96
  7  ω   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00  30.00  162
  8  ω    -27.00  42.00   0.50    0.76    --   45.19 -57.00 -30.00  138
  9  ω    -30.00  16.00   0.50    0.76    --   45.19 -38.00   0.00   92
 10  ω    -30.00  16.00   0.50    0.76    --   45.19 -38.00  30.00   92
 11  ω   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00 120.00   98
 12  ω   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00 -90.00   98
 13  ω   -139.00 -90.00   0.50    3.03    --  -97.00 -15.00  90.00   98
 14  ω    -54.00 -23.00   0.50    3.03    --  -97.00  61.00-120.00   62
 15  ω    -54.00 -23.00   0.50    3.03    --  -97.00  61.00 120.00   62
 16  ω    -54.00 -23.00   0.50    3.03    --  -97.00  61.00  60.00   62
 17  ω    -54.00 -23.00   0.50    3.03    --  -97.00  61.00-150.00   62
 18  ω     37.00  72.00   0.50    3.03    --  109.75 -77.00-180.00   70
 19  ω    104.00 133.00   0.50    3.03    --  109.75  15.00   0.00   58
 20  ω    104.00 133.00   0.50    3.03    --  109.75  15.00-120.00   58
 21  ω     37.00  72.00   0.50    3.03    --  109.75 -77.00 -90.00   70
 22  ω     37.00  72.00   0.50    3.03    --  109.75 -77.00  30.00   70
 23  ω    104.00 133.00   0.50    3.03    --  109.75  15.00  60.00   58
 24  ω    104.00 163.00   0.50    3.03    --  109.75  30.00-180.00  118
 25  ω     37.00  72.00   0.50    3.03    --  109.75 -77.00   0.00   70
 26  ω     37.00  72.00   0.50    3.03    --  109.75 -77.00 150.00   70
 27  ω    104.00 163.00   0.50    3.03    --  109.75  30.00   0.00  118
 28  ω   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00 120.00  162
 29  ω   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00-150.00  162
 30  ω   -120.00 -39.00   0.50    0.76    --  -45.19 -38.00 -60.00  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1516700000
_diffrn_orient_matrix_UB_12      -0.0495689000
_diffrn_orient_matrix_UB_13      0.0145108000
_diffrn_orient_matrix_UB_21      -0.0200761000
_diffrn_orient_matrix_UB_22      0.0042944000
_diffrn_orient_matrix_UB_23      0.1228206000
_diffrn_orient_matrix_UB_31      -0.2819344000
_diffrn_orient_matrix_UB_32      -0.0269775000
_diffrn_orient_matrix_UB_33      -0.0071445000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2923
_reflns_number_total             3254
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0402
_refine_ls_restrained_S_all      1.062
_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)+(0.0313P)²+0.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0957
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C12(H12), C14(H14), C15(H15),
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
;
_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
O1 O 0.54746(19) 0.34895(3) 0.17743(7) 0.0221(2) Uani 1 1 d . . . . .
N1 N 0.7621(2) 0.38025(4) 0.49486(9) 0.0270(3) Uani 1 1 d . . . . .
C1 C 0.8393(3) 0.39800(5) 0.30358(10) 0.0214(3) Uani 1 1 d . . . . .
C2 C 0.9868(3) 0.42495(5) 0.22745(11) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.950215 0.419718 0.152712 0.028 Uiso 1 1 calc R U . . .
C3 C 1.1827(3) 0.45867(5) 0.26192(12) 0.0258(3) Uani 1 1 d . . . . .
H3 H 1.281885 0.476842 0.210871 0.031 Uiso 1 1 calc R U . . .
C4 C 1.2380(3) 0.46652(5) 0.37282(12) 0.0280(3) Uani 1 1 d . . . . .
H4 H 1.373278 0.490163 0.395772 0.034 Uiso 1 1 calc R U . . .
C5 C 1.0987(3) 0.44045(5) 0.44789(12) 0.0275(3) Uani 1 1 d . . . . .
H5 H 1.139364 0.446078 0.522244 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8955(3) 0.40532(5) 0.41574(11) 0.0237(3) Uani 1 1 d . . . . .
C7 C 0.5687(3) 0.34829(5) 0.46580(11) 0.0255(3) Uani 1 1 d . . . . .
H7 H 0.474243 0.331501 0.520293 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4947(3) 0.33772(5) 0.35722(11) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.6335(3) 0.36262(5) 0.27927(10) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.3447(3) 0.31337(5) 0.19099(10) 0.0214(3) Uani 1 1 d . . . . .
C11 C 0.3026(3) 0.30503(5) 0.29983(10) 0.0207(3) Uani 1 1 d . . . . .
C12 C 0.1035(3) 0.27055(5) 0.32783(11) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.069695 0.264647 0.401333 0.027 Uiso 1 1 calc R U . . .
C13 C -0.0450(3) 0.24492(5) 0.24776(11) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.0059(3) 0.25445(5) 0.13939(11) 0.0267(3) Uani 1 1 d . . . . .
H14 H -0.096068 0.236656 0.085103 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2005(3) 0.28906(5) 0.10885(11) 0.0260(3) Uani 1 1 d . . . . .
H15 H 0.232158 0.295570 0.035426 0.031 Uiso 1 1 calc R U . . .
C16 C -0.2521(3) 0.20601(5) 0.27752(12) 0.0253(3) Uani 1 1 d . . . . .
H16A H -0.410254 0.206084 0.223850 0.030 Uiso 1 1 calc R U . . .
H16B H -0.325721 0.214112 0.348396 0.030 Uiso 1 1 calc R U . . .
C17 C -0.1220(3) 0.15437(5) 0.28253(11) 0.0230(3) Uani 1 1 d . . . . .
H17A H -0.061439 0.145133 0.210278 0.028 Uiso 1 1 calc R U . . .
H17B H 0.044607 0.154814 0.332181 0.028 Uiso 1 1 calc R U . . .
C18 C -0.3249(3) 0.11658(5) 0.32031(11) 0.0222(3) Uani 1 1 d . . . . .
C19 C -0.4773(3) 0.08727(5) 0.24759(11) 0.0243(3) Uani 1 1 d . . . . .
H19 H -0.449072 0.090377 0.172846 0.029 Uiso 1 1 calc R U . . .
C20 C -0.6703(3) 0.05349(5) 0.28272(11) 0.0262(3) Uani 1 1 d . . . . .
H20 H -0.774058 0.033938 0.232039 0.031 Uiso 1 1 calc R U . . .
C21 C -0.7114(3) 0.04831(5) 0.39191(12) 0.0271(3) Uani 1 1 d . . . . .
H21 H -0.841421 0.024958 0.416166 0.033 Uiso 1 1 calc R U . . .
C22 C -0.5619(3) 0.07738(5) 0.46516(12) 0.0291(3) Uani 1 1 d . . . . .
H22 H -0.590145 0.074161 0.539878 0.035 Uiso 1 1 calc R U . . .
C23 C -0.3705(3) 0.11125(5) 0.42948(11) 0.0268(3) Uani 1 1 d . . . . .
H23 H -0.268990 0.131093 0.480293 0.032 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
O1 C9 1.3679(15) . ?
O1 C10 1.3894(15) . ?
N1 C6 1.3793(18) . ?
N1 C7 1.3122(19) . ?
C1 C2 1.4137(19) . ?
C1 C6 1.4246(19) . ?
C1 C9 1.4037(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3703(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.411(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.371(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.412(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.4123(19) . ?
C8 C9 1.3797(18) . ?
C8 C11 1.4480(19) . ?
C10 C11 1.3974(18) . ?
C10 C15 1.3792(19) . ?
C11 C12 1.3957(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3882(19) . ?
C13 C14 1.406(2) . ?
C13 C16 1.5105(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.3920(19) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5384(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5071(18) . ?
C18 C19 1.3906(19) . ?
C18 C23 1.3937(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.3903(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.389(2) . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C10 105.20(10) . . ?
C7 N1 C6 118.49(12) . . ?
C2 C1 C6 120.36(12) . . ?
C9 C1 C2 125.51(12) . . ?
C9 C1 C6 114.13(12) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.72(13) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.34(13) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.81(13) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.63(13) . . ?
C6 C5 H5 119.7 . . ?
N1 C6 C1 123.82(12) . . ?
N1 C6 C5 118.04(12) . . ?
C5 C6 C1 118.14(13) . . ?
N1 C7 H7 118.5 . . ?
N1 C7 C8 123.00(13) . . ?
C8 C7 H7 118.5 . . ?
C7 C8 C11 136.55(13) . . ?
C9 C8 C7 117.63(12) . . ?
C9 C8 C11 105.81(11) . . ?
O1 C9 C1 124.60(12) . . ?
O1 C9 C8 112.48(11) . . ?
C8 C9 C1 122.92(12) . . ?
O1 C10 C11 111.31(11) . . ?
C15 C10 O1 125.23(12) . . ?
C15 C10 C11 123.46(12) . . ?
C10 C11 C8 105.20(11) . . ?
C12 C11 C8 136.00(12) . . ?
C12 C11 C10 118.80(12) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.67(12) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 119.39(12) . . ?
C12 C13 C16 119.97(12) . . ?
C14 C13 C16 120.61(12) . . ?
C13 C14 H14 118.8 . . ?
C15 C14 C13 122.31(13) . . ?
C15 C14 H14 118.8 . . ?
C10 C15 C14 116.37(13) . . ?
C10 C15 H15 121.8 . . ?
C14 C15 H15 121.8 . . ?
C13 C16 H16A 109.1 . . ?
C13 C16 H16B 109.1 . . ?
C13 C16 C17 112.29(11) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 C16 111.62(11) . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C19 C18 C17 121.19(12) . . ?
C19 C18 C23 118.32(12) . . ?
C23 C18 C17 120.46(12) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.94(13) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.03(13) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.63(13) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.04(13) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.03(13) . . ?
C22 C23 H23 119.5 . . ?

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
O1 C10 C11 C8 -0.31(14) . . . . ?
O1 C10 C11 C12 179.47(11) . . . . ?
O1 C10 C15 C14 179.75(12) . . . . ?
N1 C7 C8 C9 -0.2(2) . . . . ?
N1 C7 C8 C11 178.39(14) . . . . ?
C1 C2 C3 C4 0.08(19) . . . . ?
C2 C1 C6 N1 -179.55(12) . . . . ?
C2 C1 C6 C5 0.79(19) . . . . ?
C2 C1 C9 O1 0.4(2) . . . . ?
C2 C1 C9 C8 -179.45(12) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
C4 C5 C6 N1 -179.94(12) . . . . ?
C4 C5 C6 C1 -0.25(19) . . . . ?
C6 N1 C7 C8 1.2(2) . . . . ?
C6 C1 C2 C3 -0.71(19) . . . . ?
C6 C1 C9 O1 -179.09(11) . . . . ?
C6 C1 C9 C8 1.04(18) . . . . ?
C7 N1 C6 C1 -1.10(19) . . . . ?
C7 N1 C6 C5 178.56(12) . . . . ?
C7 C8 C9 O1 179.16(11) . . . . ?
C7 C8 C9 C1 -0.96(19) . . . . ?
C7 C8 C11 C10 -178.64(15) . . . . ?
C7 C8 C11 C12 1.6(3) . . . . ?
C8 C11 C12 C13 -179.43(14) . . . . ?
C9 O1 C10 C11 0.39(14) . . . . ?
C9 O1 C10 C15 -179.78(13) . . . . ?
C9 C1 C2 C3 179.81(13) . . . . ?
C9 C1 C6 N1 0.00(18) . . . . ?
C9 C1 C6 C5 -179.67(12) . . . . ?
C9 C8 C11 C10 0.10(14) . . . . ?
C9 C8 C11 C12 -179.62(14) . . . . ?
C10 O1 C9 C1 179.80(12) . . . . ?
C10 O1 C9 C8 -0.32(14) . . . . ?
C10 C11 C12 C13 0.87(18) . . . . ?
C11 C8 C9 O1 0.14(14) . . . . ?
C11 C8 C9 C1 -179.98(12) . . . . ?
C11 C10 C15 C14 -0.4(2) . . . . ?
C11 C12 C13 C14 -0.57(19) . . . . ?
C11 C12 C13 C16 177.40(12) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C12 C13 C16 C17 -93.23(15) . . . . ?
C13 C14 C15 C10 0.7(2) . . . . ?
C13 C16 C17 C18 175.75(11) . . . . ?
C14 C13 C16 C17 84.72(16) . . . . ?
C15 C10 C11 C8 179.86(13) . . . . ?
C15 C10 C11 C12 -0.4(2) . . . . ?
C16 C13 C14 C15 -178.22(13) . . . . ?
C16 C17 C18 C19 97.61(15) . . . . ?
C16 C17 C18 C23 -80.43(16) . . . . ?
C17 C18 C19 C20 -178.07(12) . . . . ?
C17 C18 C23 C22 178.44(13) . . . . ?
C18 C19 C20 C21 -0.6(2) . . . . ?
C19 C18 C23 C22 0.3(2) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C21 C22 C23 -0.5(2) . . . . ?
C21 C22 C23 C18 -0.1(2) . . . . ?
C23 C18 C19 C20 0.0(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id 'RAK-398 MeOH'
_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 1.528
_oxdiff_exptl_absorpt_empirical_full_min 0.803
####################################################################### 
# 
# 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_2022acc0021_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2204818'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-01
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 O'
_chemical_formula_sum            'C20 H16 O'
_chemical_formula_weight         272.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12O1
_chemical_oxdiff_usercomment     RAK-437
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3822(4)
_cell_length_b                   10.2110(8)
_cell_length_c                   11.3886(12)
_cell_angle_alpha                84.533(7)
_cell_angle_beta                 89.069(7)
_cell_angle_gamma                74.931(6)
_cell_volume                     713.37(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2600
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7330
_cell_measurement_theta_min      3.8850
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.592
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 5 1 0.0553
-2 -5 -1 0.0553
4 -2 -1 0.0724
-4 2 1 0.0724
-1 0 5 0.0080
1 0 -5 0.0080

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_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
2.0068 5.0117 0.9920 0.7245 -0.3241 -0.1865
-2.0068 -5.0117 -0.9920 -0.7245 0.3241 0.1865
3.9993 -2.0059 -1.0241 -0.1447 0.0512 -1.1168
-3.9993 2.0059 1.0241 0.1447 -0.0512 1.1168
-0.9880 -0.0032 5.0031 -0.2364 -0.6106 0.3026
0.9880 0.0032 -5.0031 0.2364 0.6106 -0.3026

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5814
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        66.473
_diffrn_reflns_theta_max         66.473
_diffrn_reflns_theta_min         3.899
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -73.00 -18.00   0.50    1.00    --  -44.84 124.00 111.00  110
  2  ω     10.00  46.00   0.50    1.00    --   44.84-124.00  32.00   72
  3  ω     50.00  77.00   0.50    1.00    --   44.84-124.00  32.00   54
  4  ω    -98.00 -72.00   0.50    5.00    --  -97.00 124.00 111.00   52
  5  ω    -63.00 -31.00   0.50    5.00    --  -97.00 124.00 111.00   64
  6  ω     89.00 142.00   0.50    5.00    --  109.75 124.00 111.00  106
  7  ω    -22.00  29.00   0.50    1.00    --  -44.84  38.00 -60.00  102
  8  ω    -28.00  12.00   0.50    1.00    --   44.84 -38.00  90.00   80
  9  ω     39.00  74.00   0.50    1.00    --   44.84  38.00 150.00   70
 10  ω     39.00  64.00   0.50    1.00    --   44.84 -77.00-150.00   50
 11  ω    -23.00  12.00   0.50    1.00    --   44.84 -77.00-150.00   70
 12  ω    -30.00  13.00   0.50    1.00    --   44.84 -38.00 120.00   86
 13  ω    -19.00  13.00   0.50    1.00    --   44.84 -38.00  30.00   64
 14  ω    -27.00   9.00   0.50    1.00    --   44.84 -38.00 -30.00   72
 15  ω    -49.00 -23.00   0.50    5.00    --  -97.00  61.00  90.00   52
 16  ω   -168.00-142.00   0.50    5.00    --  -97.00 -30.00  90.00   52
 17  ω    -92.00 -65.00   0.50    5.00    --  -97.00  99.00  69.90   54
 18  ω    -51.00 -25.00   0.50    5.00    --  -97.00  99.00  69.90   52
 19  ω   -138.00 -92.00   0.50    5.00    --  -97.00 -15.00-180.00   92
 20  ω    -93.00 -65.00   0.50    5.00    --  -97.00  93.00-142.12   56
 21  ω    -92.00 -37.00   0.50    5.00    --  -97.00  96.00 -50.71  110
 22  ω    -92.00 -23.00   0.50    5.00    --  -97.00  90.00 134.20  138
 23  ω   -138.00 -90.00   0.50    5.00    --  -97.00 -30.00  90.00   96
 24  ω   -155.00-130.00   0.50    5.00    --  -97.00-124.00  32.00   50
 25  ω    105.00 155.00   0.50    5.00    --  109.75  30.00  30.00  100
 26  ω     41.00  71.00   0.50    5.00    --  109.75 -77.00  90.00   60
 27  ω     37.00  65.00   0.50    5.00    --  109.75 -77.00-180.00   56
 28  ω    106.00 131.00   0.50    5.00    --  109.75  15.00 -60.00   50
 29  ω     39.00  67.00   0.50    5.00    --  109.75 -77.00-120.00   56
 30  ω    105.00 130.00   0.50    5.00    --  109.75  15.00   0.00   50
 31  ω     41.00  69.00   0.50    5.00    --  109.75 -77.00  30.00   56
 32  ω     37.00  71.00   0.50    5.00    --  109.75 -77.00 -60.00   68
 33  ω    104.00 129.00   0.50    5.00    --  109.75  15.00  90.00   50
 34  ω     39.00  68.00   0.50    5.00    --  109.75 -77.00 120.00   58
 35  ω     39.00  88.00   0.50    5.00    --  109.75 -95.00  30.00   98
 36  ω    104.00 129.00   0.50    5.00    --  109.75  15.00  30.00   50
 37  ω     63.00  93.00   0.50    5.00    --  109.75 -95.00   0.00   60
 38  ω     41.00  71.00   0.50    5.00    --  109.75 -77.00-150.00   60
 39  ω    104.00 129.00   0.50    5.00    --  109.75  15.00-180.00   50
 40  ω     69.00  95.00   0.50    5.00    --  109.75-125.00 -30.00   52
 41  ω     57.00  91.00   0.50    5.00    --  109.75 -95.00 -90.00   68
 42  ω     52.00  78.00   0.50    5.00    --  109.75 -95.00  90.00   52
 43  ω    109.00 151.00   0.50    5.00    --  109.75  30.00-120.00   84
 44  ω    104.00 129.00   0.50    5.00    --  109.75  15.00 -30.00   50
 45  ω    114.00 158.00   0.50    5.00    --  109.75  30.00 -60.00   88
 46  ω     68.00  94.00   0.50    5.00    --  109.75-124.00  32.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0247354000
_diffrn_orient_matrix_UB_12      0.1430337000
_diffrn_orient_matrix_UB_13      -0.0422820000
_diffrn_orient_matrix_UB_21      -0.0331476000
_diffrn_orient_matrix_UB_22      -0.0259462000
_diffrn_orient_matrix_UB_23      -0.1286079000
_diffrn_orient_matrix_UB_31      -0.2465464000
_diffrn_orient_matrix_UB_32      0.0591587000
_diffrn_orient_matrix_UB_33      0.0118277000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2067
_reflns_number_total             2417
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.566
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1453
_refine_ls_R_factor_gt           0.1351
_refine_ls_restrained_S_all      1.171
_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)+(0.0852P)²+9.0160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3868
_refine_ls_wR_factor_ref         0.3906
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20)
;
_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
C1 C 1.0484(12) 0.5733(8) 0.6898(7) 0.0282(18) Uani 1 1 d . . . . .
C2 C 1.2423(13) 0.4946(8) 0.6493(7) 0.0282(18) Uani 1 1 d . . . . .
H2 H 1.260033 0.473622 0.569646 0.034 Uiso 1 1 calc R U . . .
C3 C 1.4089(12) 0.4483(8) 0.7320(8) 0.0314(19) Uani 1 1 d . . . . .
H3 H 1.546522 0.396636 0.708096 0.038 Uiso 1 1 calc R U . . .
C4 C 1.3782(12) 0.4763(8) 0.8503(7) 0.0292(18) Uani 1 1 d . . . . .
H4 H 1.493433 0.440266 0.905577 0.035 Uiso 1 1 calc R U . . .
C5 C 1.1828(13) 0.5554(8) 0.8878(7) 0.0289(18) Uani 1 1 d . . . . .
H5 H 1.164079 0.575872 0.967563 0.035 Uiso 1 1 calc R U . . .
C6 C 1.0127(13) 0.6048(8) 0.8053(7) 0.0268(17) Uani 1 1 d . . . . .
C7 C 0.7925(13) 0.6894(8) 0.8078(7) 0.0272(17) Uani 1 1 d . . . . .
C8 C 0.6538(13) 0.7555(8) 0.8937(7) 0.0269(17) Uani 1 1 d . . . . .
H8 H 0.701084 0.749902 0.973067 0.032 Uiso 1 1 calc R U . . .
C9 C 0.4488(13) 0.8279(8) 0.8592(7) 0.0302(18) Uani 1 1 d . . . . .
H9 H 0.353123 0.872161 0.916526 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3745(13) 0.8393(8) 0.7427(7) 0.0287(17) Uani 1 1 d . . . . .
H10 H 0.232560 0.893770 0.722613 0.034 Uiso 1 1 calc R U . . .
C11 C 0.5036(12) 0.7729(7) 0.6560(7) 0.0256(17) Uani 1 1 d . . . . .
C12 C 0.7122(12) 0.7002(7) 0.6942(7) 0.0240(16) Uani 1 1 d . . . . .
C13 C 0.4381(12) 0.7752(8) 0.5288(7) 0.0275(17) Uani 1 1 d . . . . .
H13A H 0.442760 0.681127 0.512211 0.033 Uiso 1 1 calc R U . . .
H13B H 0.546396 0.805957 0.477668 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2138(13) 0.8665(8) 0.4957(7) 0.0289(18) Uani 1 1 d . . . . .
H14A H 0.104315 0.836976 0.546738 0.035 Uiso 1 1 calc R U . . .
H14B H 0.208680 0.961443 0.510079 0.035 Uiso 1 1 calc R U . . .
C15 C 0.1576(12) 0.8623(8) 0.3676(7) 0.0288(18) Uani 1 1 d . . . . .
C16 C 0.2447(13) 0.9326(8) 0.2780(7) 0.0320(19) Uani 1 1 d . . . . .
H16 H 0.337930 0.986489 0.297070 0.038 Uiso 1 1 calc R U . . .
C17 C 0.1979(14) 0.9255(9) 0.1609(8) 0.035(2) Uani 1 1 d . . . . .
H17 H 0.256858 0.975824 0.100661 0.042 Uiso 1 1 calc R U . . .
C18 C 0.0666(14) 0.8460(8) 0.1313(7) 0.0319(19) Uani 1 1 d . . . . .
H18 H 0.036707 0.840371 0.050771 0.038 Uiso 1 1 calc R U . . .
C19 C -0.0219(13) 0.7743(8) 0.2192(8) 0.0333(19) Uani 1 1 d . . . . .
H19 H -0.112180 0.718968 0.198873 0.040 Uiso 1 1 calc R U . . .
C20 C 0.0213(12) 0.7829(8) 0.3378(7) 0.0294(18) Uani 1 1 d . . . . .
H20 H -0.041876 0.734986 0.398076 0.035 Uiso 1 1 calc R U . . .
O1 O 0.8655(8) 0.6297(5) 0.6194(5) 0.0256(13) Uani 1 1 d . . . . .


_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
C1 C2 1.388(11) . ?
C1 C6 1.385(12) . ?
C1 O1 1.389(9) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(11) . ?
C5 H5 0.9500 . ?
C5 C6 1.405(11) . ?
C6 C7 1.447(11) . ?
C7 C8 1.408(11) . ?
C7 C12 1.383(11) . ?
C8 H8 0.9500 . ?
C8 C9 1.368(11) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(11) . ?
C11 C12 1.399(11) . ?
C11 C13 1.510(11) . ?
C12 O1 1.387(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.522(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(11) . ?
C15 C16 1.384(12) . ?
C15 C20 1.399(11) . ?
C16 H16 0.9500 . ?
C16 C17 1.383(12) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(12) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.399(12) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 O1 124.1(7) . . ?
C6 C1 C2 124.3(7) . . ?
C6 C1 O1 111.6(7) . . ?
C1 C2 H2 122.0 . . ?
C1 C2 C3 116.1(8) . . ?
C3 C2 H2 122.0 . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.3(7) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.1(7) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(8) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 118.7(7) . . ?
C1 C6 C7 105.8(7) . . ?
C5 C6 C7 135.5(8) . . ?
C8 C7 C6 136.2(7) . . ?
C12 C7 C6 105.8(7) . . ?
C12 C7 C8 118.0(7) . . ?
C7 C8 H8 121.0 . . ?
C9 C8 C7 118.0(7) . . ?
C9 C8 H8 121.0 . . ?
C8 C9 H9 118.7 . . ?
C8 C9 C10 122.5(7) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.4(7) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 C12 114.5(7) . . ?
C10 C11 C13 125.8(7) . . ?
C12 C11 C13 119.7(7) . . ?
C7 C12 C11 125.6(7) . . ?
C7 C12 O1 111.8(6) . . ?
O1 C12 C11 122.7(7) . . ?
C11 C13 H13A 108.6 . . ?
C11 C13 H13B 108.6 . . ?
C11 C13 C14 114.8(7) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C15 C14 C13 111.9(6) . . ?
C15 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C16 C15 C14 121.1(7) . . ?
C16 C15 C20 118.7(8) . . ?
C20 C15 C14 120.2(7) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 121.0(8) . . ?
C17 C16 H16 119.5 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(8) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.8(8) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(8) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 119.9(8) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C12 O1 C1 105.0(6) . . ?

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
C1 C2 C3 C4 2.2(11) . . . . ?
C1 C6 C7 C8 179.9(9) . . . . ?
C1 C6 C7 C12 0.9(8) . . . . ?
C2 C1 C6 C5 0.5(11) . . . . ?
C2 C1 C6 C7 179.2(7) . . . . ?
C2 C1 O1 C12 -179.5(7) . . . . ?
C2 C3 C4 C5 -2.4(12) . . . . ?
C3 C4 C5 C6 1.6(12) . . . . ?
C4 C5 C6 C1 -0.6(11) . . . . ?
C4 C5 C6 C7 -178.9(8) . . . . ?
C5 C6 C7 C8 -1.7(16) . . . . ?
C5 C6 C7 C12 179.4(8) . . . . ?
C6 C1 C2 C3 -1.2(11) . . . . ?
C6 C1 O1 C12 0.8(8) . . . . ?
C6 C7 C8 C9 -179.7(8) . . . . ?
C6 C7 C12 C11 179.8(7) . . . . ?
C6 C7 C12 O1 -0.5(8) . . . . ?
C7 C8 C9 C10 -0.6(12) . . . . ?
C7 C12 O1 C1 -0.2(8) . . . . ?
C8 C7 C12 C11 0.7(11) . . . . ?
C8 C7 C12 O1 -179.6(6) . . . . ?
C8 C9 C10 C11 2.4(13) . . . . ?
C9 C10 C11 C12 -2.5(11) . . . . ?
C9 C10 C11 C13 178.4(8) . . . . ?
C10 C11 C12 C7 1.0(11) . . . . ?
C10 C11 C12 O1 -178.7(7) . . . . ?
C10 C11 C13 C14 3.7(11) . . . . ?
C11 C12 O1 C1 179.5(7) . . . . ?
C11 C13 C14 C15 -179.1(7) . . . . ?
C12 C7 C8 C9 -0.8(11) . . . . ?
C12 C11 C13 C14 -175.4(7) . . . . ?
C13 C11 C12 C7 -179.8(7) . . . . ?
C13 C11 C12 O1 0.5(11) . . . . ?
C13 C14 C15 C16 -77.0(9) . . . . ?
C13 C14 C15 C20 100.9(8) . . . . ?
C14 C15 C16 C17 178.2(7) . . . . ?
C14 C15 C20 C19 -177.0(7) . . . . ?
C15 C16 C17 C18 -1.2(13) . . . . ?
C16 C15 C20 C19 1.0(11) . . . . ?
C16 C17 C18 C19 1.0(13) . . . . ?
C17 C18 C19 C20 0.3(12) . . . . ?
C18 C19 C20 C15 -1.2(12) . . . . ?
C20 C15 C16 C17 0.3(12) . . . . ?
O1 C1 C2 C3 179.1(7) . . . . ?
O1 C1 C6 C5 -179.9(6) . . . . ?
O1 C1 C6 C7 -1.1(8) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-437
_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 1.738
_oxdiff_exptl_absorpt_empirical_full_min 0.499
####################################################################### 
# 
# 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_2022acc0019_r1_100k
_database_code_depnum_ccdc_archive 'CCDC 2201481'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-08-15 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-08-15
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O3'
_chemical_formula_sum            'C23 H23 N O3'
_chemical_formula_weight         361.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N1 S1 O4'
_chemical_oxdiff_usercomment     EA-8-552
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.0444(9)
_cell_length_b                   5.6218(3)
_cell_length_c                   27.7622(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.864(7)
_cell_angle_gamma                90
_cell_volume                     1852.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2681
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.8540
_cell_measurement_theta_min      3.9550
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 2 0.0076
1 -5 -2 0.0076
1 0 5 0.0456
-1 0 -5 0.0456
-3 0 5 0.0060
3 0 -5 0.0060

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
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
-0.9886 4.9985 2.0220 0.0105 0.0054 0.6345
0.9886 -4.9985 -2.0220 -0.0105 -0.0054 -0.6345
0.9988 0.0001 4.9989 -0.1097 0.1047 0.0047
-0.9988 -0.0001 -4.9989 0.1097 -0.1047 -0.0047
-2.9978 -0.0007 4.9930 0.1223 0.1600 0.0194
2.9978 0.0007 -4.9930 -0.1223 -0.1600 -0.0194

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.1001
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            12007
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.328
_diffrn_reflns_theta_min         3.919
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  28.00   0.50  100.00    --   11.29 -77.00 -30.00   92
  2  ω      0.00  59.00   0.50  100.00    --   11.29  57.00 -30.00  118
  3  ω     22.00  62.00   0.50  100.00    --   11.29  57.00-180.00   80
  4  ω    -18.00   9.00   0.50  100.00    --   11.29 -77.00 -90.00   54
  5  ω     21.00  89.00   0.50  100.00    --   11.29  19.00 -90.00  136
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0580358000
_diffrn_orient_matrix_UB_12      -0.0051950000
_diffrn_orient_matrix_UB_13      -0.0103479000
_diffrn_orient_matrix_UB_21      -0.0138610000
_diffrn_orient_matrix_UB_22      -0.0112574000
_diffrn_orient_matrix_UB_23      0.0237219000
_diffrn_orient_matrix_UB_31      -0.0036953000
_diffrn_orient_matrix_UB_32      0.1255317000
_diffrn_orient_matrix_UB_33      0.0016749000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2595
_reflns_number_total             4623
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1270
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      0.992
_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)+(0.0511P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1166
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C16(H16), C18(H18), C19(H19), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.86669(10) 1.2678(2) 0.46303(4) 0.0229(3) Uani 1 1 d . . . . .
O2 O 0.69728(12) 1.4484(2) 0.44885(5) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.76307(10) 0.43450(19) 0.63751(4) 0.0209(3) Uani 1 1 d . . . . .
N1 N 0.48213(12) 0.7120(2) 0.68531(5) 0.0233(4) Uani 1 1 d . . . . .
C1 C 0.83932(17) 1.2893(3) 0.37387(6) 0.0296(5) Uani 1 1 d . . . . .
H1A H 0.836197 1.115211 0.374747 0.044 Uiso 1 1 calc R U . . .
H1B H 0.874489 1.339996 0.346239 0.044 Uiso 1 1 calc R U . . .
H1C H 0.762738 1.353909 0.370080 0.044 Uiso 1 1 calc R U . . .
C2 C 0.90836(16) 1.3806(3) 0.42123(6) 0.0234(4) Uani 1 1 d . . . . .
C3 C 1.02889(17) 1.2939(3) 0.42751(7) 0.0310(5) Uani 1 1 d . . . . .
H3A H 1.071478 1.356685 0.458118 0.047 Uiso 1 1 calc R U . . .
H3B H 1.063276 1.349143 0.399991 0.047 Uiso 1 1 calc R U . . .
H3C H 1.029984 1.119622 0.428504 0.047 Uiso 1 1 calc R U . . .
C4 C 0.90579(19) 1.6507(3) 0.42515(7) 0.0317(5) Uani 1 1 d . . . . .
H4A H 0.827401 1.705566 0.419656 0.048 Uiso 1 1 calc R U . . .
H4B H 0.945185 1.720921 0.400505 0.048 Uiso 1 1 calc R U . . .
H4C H 0.943133 1.699484 0.457827 0.048 Uiso 1 1 calc R U . . .
C5 C 0.76141(16) 1.3076(3) 0.47114(7) 0.0255(4) Uani 1 1 d . . . . .
C6 C 0.73485(16) 1.1512(3) 0.51172(7) 0.0252(4) Uani 1 1 d . . . . .
H6A H 0.795783 1.166492 0.540411 0.030 Uiso 1 1 calc R U . . .
H6B H 0.732442 0.983268 0.500862 0.030 Uiso 1 1 calc R U . . .
C7 C 0.62341(15) 1.2148(3) 0.52674(6) 0.0219(4) Uani 1 1 d . . . . .
H7A H 0.626585 1.383484 0.537132 0.026 Uiso 1 1 calc R U . . .
H7B H 0.563407 1.200960 0.497660 0.026 Uiso 1 1 calc R U . . .
C8 C 0.59005(15) 1.0658(3) 0.56741(6) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.64843(15) 0.8685(3) 0.58695(6) 0.0196(4) Uani 1 1 d . . . . .
H9 H 0.712406 0.816116 0.574075 0.024 Uiso 1 1 calc R U . . .
C10 C 0.61412(14) 0.7422(3) 0.62616(6) 0.0185(4) Uani 1 1 d . . . . .
C11 C 0.51829(15) 0.8178(3) 0.64573(6) 0.0202(4) Uani 1 1 d . . . . .
C12 C 0.45822(15) 1.0172(3) 0.62401(7) 0.0231(4) Uani 1 1 d . . . . .
H12 H 0.392491 1.068787 0.635630 0.028 Uiso 1 1 calc R U . . .
C13 C 0.49333(15) 1.1367(3) 0.58654(6) 0.0221(4) Uani 1 1 d . . . . .
H13 H 0.451744 1.271366 0.572879 0.027 Uiso 1 1 calc R U . . .
C14 C 0.66945(14) 0.5444(3) 0.65016(6) 0.0186(4) Uani 1 1 d . . . . .
C15 C 0.63570(15) 0.4382(3) 0.68993(6) 0.0188(4) Uani 1 1 d . . . . .
C16 C 0.54017(15) 0.5300(3) 0.70640(6) 0.0229(4) Uani 1 1 d . . . . .
H16 H 0.516478 0.457729 0.733870 0.027 Uiso 1 1 calc R U . . .
C17 C 0.78831(15) 0.2495(3) 0.67110(6) 0.0192(4) Uani 1 1 d . . . . .
C18 C 0.87431(15) 0.0884(3) 0.67208(7) 0.0236(4) Uani 1 1 d . . . . .
H18 H 0.924468 0.095032 0.649173 0.028 Uiso 1 1 calc R U . . .
C19 C 0.88433(16) -0.0849(3) 0.70823(6) 0.0235(4) Uani 1 1 d . . . . .
H19 H 0.942579 -0.199999 0.709755 0.028 Uiso 1 1 calc R U . . .
C20 C 0.81142(15) -0.0962(3) 0.74264(6) 0.0228(4) Uani 1 1 d . . . . .
C21 C 0.72584(15) 0.0699(3) 0.74059(6) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.676287 0.065765 0.763771 0.025 Uiso 1 1 calc R U . . .
C22 C 0.71314(14) 0.2438(3) 0.70402(6) 0.0189(4) Uani 1 1 d . . . . .
C23 C 0.82619(17) -0.2876(3) 0.78153(7) 0.0280(4) Uani 1 1 d . . . . .
H23A H 0.881816 -0.235312 0.809511 0.042 Uiso 1 1 calc R U . . .
H23B H 0.852381 -0.434372 0.768084 0.042 Uiso 1 1 calc R U . . .
H23C H 0.753925 -0.316961 0.792177 0.042 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
O1 C2 1.483(2) . ?
O1 C5 1.344(2) . ?
O2 C5 1.201(2) . ?
O3 C14 1.383(2) . ?
O3 C17 1.3951(19) . ?
N1 C11 1.384(2) . ?
N1 C16 1.319(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.519(3) . ?
C2 C3 1.513(3) . ?
C2 C4 1.523(2) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.506(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.515(2) . ?
C8 C9 1.374(2) . ?
C8 C13 1.418(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.419(2) . ?
C10 C11 1.422(2) . ?
C10 C14 1.404(2) . ?
C11 C12 1.412(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.365(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.377(2) . ?
C15 C16 1.407(2) . ?
C15 C22 1.446(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.373(2) . ?
C17 C22 1.393(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.405(3) . ?
C20 C21 1.385(3) . ?
C20 C23 1.513(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.399(2) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C5 O1 C2 121.00(14) . . ?
C14 O3 C17 104.90(13) . . ?
C16 N1 C11 118.10(15) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 108.93(14) . . ?
O1 C2 C3 102.63(14) . . ?
O1 C2 C4 110.89(14) . . ?
C1 C2 C4 112.56(16) . . ?
C3 C2 C1 111.29(16) . . ?
C3 C2 C4 110.11(17) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 110.81(15) . . ?
O2 C5 O1 124.44(17) . . ?
O2 C5 C6 124.75(17) . . ?
C5 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
C5 C6 C7 112.32(15) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
C6 C7 H7A 108.3 . . ?
C6 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C8 C7 C6 115.80(15) . . ?
C8 C7 H7A 108.3 . . ?
C8 C7 H7B 108.3 . . ?
C9 C8 C7 123.89(16) . . ?
C9 C8 C13 118.49(16) . . ?
C13 C8 C7 117.61(15) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.67(16) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.38(15) . . ?
C14 C10 C9 125.68(16) . . ?
C14 C10 C11 113.91(15) . . ?
N1 C11 C10 124.16(15) . . ?
N1 C11 C12 118.18(15) . . ?
C12 C11 C10 117.63(15) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.89(16) . . ?
C13 C12 H12 119.6 . . ?
C8 C13 H13 119.0 . . ?
C12 C13 C8 121.91(16) . . ?
C12 C13 H13 119.0 . . ?
O3 C14 C10 125.07(15) . . ?
C15 C14 O3 112.05(15) . . ?
C15 C14 C10 122.88(16) . . ?
C14 C15 C16 118.15(16) . . ?
C14 C15 C22 106.23(15) . . ?
C16 C15 C22 135.61(16) . . ?
N1 C16 C15 122.77(16) . . ?
N1 C16 H16 118.6 . . ?
C15 C16 H16 118.6 . . ?
C18 C17 O3 125.62(16) . . ?
C18 C17 C22 123.01(16) . . ?
C22 C17 O3 111.36(14) . . ?
C17 C18 H18 121.7 . . ?
C17 C18 C19 116.68(17) . . ?
C19 C18 H18 121.7 . . ?
C18 C19 H19 118.8 . . ?
C18 C19 C20 122.39(17) . . ?
C20 C19 H19 118.8 . . ?
C19 C20 C23 120.42(16) . . ?
C21 C20 C19 119.29(16) . . ?
C21 C20 C23 120.30(17) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.28(17) . . ?
C22 C21 H21 120.4 . . ?
C17 C22 C15 105.46(14) . . ?
C17 C22 C21 119.34(16) . . ?
C21 C22 C15 135.20(16) . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C5 C6 C7 171.99(15) . . . . ?
O2 C5 C6 C7 -8.3(3) . . . . ?
O3 C14 C15 C16 -179.10(15) . . . . ?
O3 C14 C15 C22 -0.23(19) . . . . ?
O3 C17 C18 C19 -179.12(15) . . . . ?
O3 C17 C22 C15 0.09(18) . . . . ?
O3 C17 C22 C21 -179.76(14) . . . . ?
N1 C11 C12 C13 176.51(16) . . . . ?
C2 O1 C5 O2 -6.6(3) . . . . ?
C2 O1 C5 C6 173.16(14) . . . . ?
C5 O1 C2 C1 -63.80(19) . . . . ?
C5 O1 C2 C3 178.15(15) . . . . ?
C5 O1 C2 C4 60.6(2) . . . . ?
C5 C6 C7 C8 179.95(14) . . . . ?
C6 C7 C8 C9 -6.7(2) . . . . ?
C6 C7 C8 C13 172.72(16) . . . . ?
C7 C8 C9 C10 177.90(15) . . . . ?
C7 C8 C13 C12 -178.39(16) . . . . ?
C8 C9 C10 C11 0.2(2) . . . . ?
C8 C9 C10 C14 -177.47(16) . . . . ?
C9 C8 C13 C12 1.0(2) . . . . ?
C9 C10 C11 N1 -176.88(16) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C9 C10 C14 O3 -3.5(3) . . . . ?
C9 C10 C14 C15 176.02(16) . . . . ?
C10 C11 C12 C13 -1.9(2) . . . . ?
C10 C14 C15 C16 1.3(2) . . . . ?
C10 C14 C15 C22 -179.84(15) . . . . ?
C11 N1 C16 C15 -0.8(2) . . . . ?
C11 C10 C14 O3 178.64(15) . . . . ?
C11 C10 C14 C15 -1.8(2) . . . . ?
C11 C12 C13 C8 0.7(3) . . . . ?
C13 C8 C9 C10 -1.5(2) . . . . ?
C14 O3 C17 C18 178.71(17) . . . . ?
C14 O3 C17 C22 -0.23(17) . . . . ?
C14 C10 C11 N1 1.1(2) . . . . ?
C14 C10 C11 C12 179.43(15) . . . . ?
C14 C15 C16 N1 0.1(3) . . . . ?
C14 C15 C22 C17 0.08(18) . . . . ?
C14 C15 C22 C21 179.90(18) . . . . ?
C16 N1 C11 C10 0.2(2) . . . . ?
C16 N1 C11 C12 -178.16(15) . . . . ?
C16 C15 C22 C17 178.65(19) . . . . ?
C16 C15 C22 C21 -1.5(3) . . . . ?
C17 O3 C14 C10 179.88(15) . . . . ?
C17 O3 C14 C15 0.28(17) . . . . ?
C17 C18 C19 C20 -0.5(3) . . . . ?
C18 C17 C22 C15 -178.88(16) . . . . ?
C18 C17 C22 C21 1.3(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C18 C19 C20 C23 -179.64(16) . . . . ?
C19 C20 C21 C22 0.6(3) . . . . ?
C20 C21 C22 C15 178.80(18) . . . . ?
C20 C21 C22 C17 -1.4(2) . . . . ?
C22 C15 C16 N1 -178.31(18) . . . . ?
C22 C17 C18 C19 -0.3(3) . . . . ?
C23 C20 C21 C22 -179.38(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id EA-8-552
_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 1.904
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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_2022acc0025_a1_100k
_database_code_depnum_ccdc_archive 'CCDC 2204956'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N O'
_chemical_formula_sum            'C19 H15 N O'
_chemical_formula_weight         273.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12H12 N1O1'
_chemical_oxdiff_usercomment     RAK-443
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'
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                   13.1980(2)
_cell_length_b                   5.61880(10)
_cell_length_c                   18.6771(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.2680(10)
_cell_angle_gamma                90
_cell_volume                     1373.91(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.8060
_cell_measurement_theta_min      3.3620
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             576
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0369
-1 3 -4 0.1623
1 -3 4 0.1623
1 0 -5 0.0222
-1 0 5 0.0222
5 0 -2 0.0097

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.06
_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
-0.9982 0.0005 0.0010 0.0575 -0.1004 0.0202
-0.9931 3.0045 -3.9887 0.1850 -0.2511 -0.8452
0.9931 -3.0045 3.9887 -0.1850 0.2511 0.8452
0.9955 0.0011 -4.9984 0.3173 0.2280 -0.1467
-0.9955 -0.0011 4.9984 -0.3173 -0.2280 0.1467
4.9897 -0.0019 -2.0037 -0.1375 0.5532 -0.1516

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1188
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19810
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.889
_diffrn_reflns_theta_min         3.376
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00   5.00   0.50    0.24    --   46.61 -29.00 155.00   50
  2  ω     47.00 103.00   0.50    0.96    --  101.75 -77.00  90.00  112
  3  ω     34.00  70.00   0.50    0.96    --  101.75 -61.00   0.00   72
  4  ω     31.00  64.00   0.50    0.96    --  101.75 -61.00 -90.00   66
  5  ω     29.00  72.00   0.50    0.96    --  101.75 -61.00-150.00   86
  6  ω     89.00 167.00   0.50    0.96    --  101.75  29.00 -43.00  156
  7  ω    125.00 152.00   0.50    0.96    --  101.75  61.00   0.00   54
  8  ω     81.00 107.00   0.50    0.96    --  101.75  77.00  30.00   52
  9  ω     86.00 115.00   0.50    0.96    --  101.75  61.00   0.00   58
 10  ω     90.00 121.00   0.50    0.96    --  101.75  45.00  30.00   62
 11  ω     79.00 104.00   0.50    0.96    --  101.75  77.00  90.00   50
 12  ω     31.00  78.00   0.50    0.24    --   46.61  77.00  30.00   94
 13  ω     24.00  75.00   0.50    0.24    --   46.61  77.00  60.00  102
 14  ω     39.00  80.00   0.50    0.24    --   46.61  57.00   0.00   82
 15  ω     39.00  66.00   0.50    0.24    --   46.61  37.00   0.00   54
 16  ω     56.00 118.00   0.50    0.24    --   46.61  29.00 -43.00  124
 17  ω     37.00 105.00   0.50    0.96    --  101.75-100.00 -89.40  136
 18  ω    -39.00  26.00   0.50    0.24    --  -46.61  37.00  90.00  130
 19  ω     -3.00  23.00   0.50    0.24    --  -46.61  19.00  90.00   52
 20  ω    -31.00  28.00   0.50    0.24    --  -46.61  29.00 -43.00  118
 21  ω   -101.00 -39.00   0.50    0.96    -- -103.00  77.00 -30.00  124
 22  ω    -63.00 -31.00   0.50    0.96    -- -103.00  61.00-120.00   64
 23  ω    -63.00 -37.00   0.50    0.96    -- -103.00  61.00  60.00   52
 24  ω    -58.00 -33.00   0.50    0.96    -- -103.00  61.00  90.00   50
 25  ω    -62.00 -31.00   0.50    0.96    -- -103.00  61.00 150.00   62
 26  ω   -114.00 -51.00   0.50    0.24    --  -46.61 -29.00 155.00  126
 27  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -78.00  46.55   50
 28  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -78.00  21.30   50
 29  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -77.00  30.00   52
 30  ω   -169.00-126.00   0.50    0.96    -- -103.00 -78.00  46.55   86
 31  ω   -172.00-146.00   0.50    0.96    -- -103.00 -78.00  21.30   52
 32  ω   -114.00 -80.00   0.50    0.96    -- -103.00 -77.00  90.00   68
 33  ω   -105.00 -80.00   0.50    0.96    -- -103.00 -77.00 120.00   50
 34  ω   -161.00-135.00   0.50    0.96    -- -103.00 -77.00 120.00   52
 35  ω   -174.00-135.00   0.50    0.96    -- -103.00 -76.00  36.03   78
 36  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -77.00  60.00   52
 37  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -76.00 113.49   52
 38  ω   -111.00 -85.00   0.50    0.96    -- -103.00 -65.00  92.30   52
 39  ω   -113.00 -88.00   0.50    0.96    -- -103.00 -58.00 120.36   50
 40  ω   -113.00 -87.00   0.50    0.96    -- -103.00 -61.00  60.00   52
 41  ω   -112.00 -86.00   0.50    0.96    -- -103.00 -61.00  55.16   52
 42  ω   -107.00 -81.00   0.50    0.96    -- -103.00 -76.00  36.03   52
 43  ω   -117.00 -91.00   0.50    0.96    -- -103.00 -54.00  -1.93   52
 44  ω   -113.00 -87.00   0.50    0.96    -- -103.00 -61.00  30.00   52
 45  ω   -115.00 -89.00   0.50    0.96    -- -103.00 -53.00  36.45   52
 46  ω   -134.00 -90.00   0.50    0.96    -- -103.00 -46.00  34.43   88
 47  ω   -165.00 -88.00   0.50    0.96    -- -103.00 -58.00  61.33  154
 48  ω   -116.00 -90.00   0.50    0.96    -- -103.00 -48.00  90.37   52
 49  ω   -115.00 -89.00   0.50    0.96    -- -103.00 -51.00 102.40   52
 50  ω   -166.00 -92.00   0.50    0.96    -- -103.00 -46.00  76.29  148
 51  ω   -156.00 -91.00   0.50    0.96    -- -103.00 -45.00  90.00  130
 52  ω   -118.00 -92.00   0.50    0.96    -- -103.00 -45.00 120.00   52
 53  ω   -156.00-131.00   0.50    0.96    -- -103.00 -29.00 155.00   50
 54  ω   -174.00-145.00   0.50    0.96    -- -103.00 -45.00 120.00   58
 55  ω   -106.00 -80.00   0.50    0.96    -- -103.00 -81.00  91.09   52
 56  ω   -104.00 -78.00   0.50    0.96    -- -103.00 -84.00 108.14   52
 57  ω   -137.00-107.00   0.50    0.96    -- -103.00-125.00 -90.00   60
 58  ω   -171.00-142.00   0.50    0.96    -- -103.00-125.00 -90.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0576883000
_diffrn_orient_matrix_UB_12      -0.0570386000
_diffrn_orient_matrix_UB_13      -0.0749742000
_diffrn_orient_matrix_UB_21      0.1005489000
_diffrn_orient_matrix_UB_22      -0.0843273000
_diffrn_orient_matrix_UB_23      -0.0255981000
_diffrn_orient_matrix_UB_31      -0.0203465000
_diffrn_orient_matrix_UB_32      -0.2545322000
_diffrn_orient_matrix_UB_33      0.0252459000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2494
_reflns_number_total             2774
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2774
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.025
_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)+(0.1035P)²+0.4243P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1564
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_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
C1 C 0.53007(10) 0.5012(3) 0.63373(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.46176(10) 0.4578(3) 0.68370(9) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.472263 0.323356 0.714607 0.027 Uiso 1 1 calc R U . . .
C3 C 0.36747(11) 0.7883(3) 0.64434(9) 0.0237(4) Uani 1 1 d . . . . .
H3 H 0.310448 0.888012 0.648720 0.028 Uiso 1 1 calc R U . . .
C4 C 0.42953(11) 0.8483(3) 0.59192(9) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.416724 0.982183 0.561041 0.029 Uiso 1 1 calc R U . . .
C5 C 0.51137(11) 0.6962(3) 0.58869(8) 0.0209(3) Uani 1 1 d . . . . .
C6 C 0.65217(10) 0.5349(3) 0.55997(8) 0.0195(3) Uani 1 1 d . . . . .
C7 C 0.62317(10) 0.3924(3) 0.61459(8) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.68359(11) 0.1973(3) 0.63900(9) 0.0213(3) Uani 1 1 d . . . . .
H8 H 0.665357 0.096157 0.676069 0.026 Uiso 1 1 calc R U . . .
C9 C 0.77131(11) 0.1573(3) 0.60687(9) 0.0233(4) Uani 1 1 d . . . . .
H9 H 0.813755 0.025602 0.622183 0.028 Uiso 1 1 calc R U . . .
C10 C 0.79879(11) 0.3070(3) 0.55223(9) 0.0222(3) Uani 1 1 d . . . . .
H10 H 0.859917 0.274067 0.532139 0.027 Uiso 1 1 calc R U . . .
C11 C 0.73998(10) 0.5018(3) 0.52637(8) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.76405(11) 0.6677(3) 0.46735(8) 0.0211(3) Uani 1 1 d . . . . .
H12A H 0.768546 0.831885 0.486725 0.025 Uiso 1 1 calc R U . . .
H12B H 0.706550 0.663274 0.427813 0.025 Uiso 1 1 calc R U . . .
C13 C 0.86281(12) 0.6120(3) 0.43574(10) 0.0277(4) Uani 1 1 d . . . . .
H13A H 0.921047 0.619435 0.474685 0.033 Uiso 1 1 calc R U . . .
H13B H 0.859141 0.447937 0.416248 0.033 Uiso 1 1 calc R U . . .
C14 C 0.88155(11) 0.7834(3) 0.37636(9) 0.0242(4) Uani 1 1 d . . . . .
C15 C 0.83105(11) 0.7550(3) 0.30644(9) 0.0252(4) Uani 1 1 d . . . . .
H15 H 0.786352 0.623746 0.295662 0.030 Uiso 1 1 calc R U . . .
C16 C 0.84570(11) 0.9169(3) 0.25280(9) 0.0253(4) Uani 1 1 d . . . . .
H16 H 0.810246 0.896900 0.205658 0.030 Uiso 1 1 calc R U . . .
C17 C 0.91184(11) 1.1084(3) 0.26731(9) 0.0253(4) Uani 1 1 d . . . . .
H17 H 0.922058 1.218560 0.230303 0.030 Uiso 1 1 calc R U . . .
C18 C 0.96269(11) 1.1369(3) 0.33641(9) 0.0261(4) Uani 1 1 d . . . . .
H18 H 1.008240 1.266732 0.346878 0.031 Uiso 1 1 calc R U . . .
C19 C 0.94715(11) 0.9760(3) 0.39025(9) 0.0253(4) Uani 1 1 d . . . . .
H19 H 0.981991 0.997818 0.437494 0.030 Uiso 1 1 calc R U . . .
N1 N 0.38184(9) 0.6010(2) 0.68909(7) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.58371(7) 0.72031(18) 0.54212(6) 0.0214(3) Uani 1 1 d . . . . .


_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
C1 C2 1.399(2) . ?
C1 C5 1.384(2) . ?
C1 C7 1.4568(19) . ?
C2 H2 0.9500 . ?
C2 N1 1.3407(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C3 N1 1.342(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(2) . ?
C5 O1 1.3772(18) . ?
C6 C7 1.388(2) . ?
C6 C11 1.398(2) . ?
C6 O1 1.3915(17) . ?
C7 C8 1.398(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.405(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 C12 1.508(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5297(19) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.513(2) . ?
C14 C15 1.398(2) . ?
C14 C19 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 136.50(14) . . ?
C5 C1 C2 117.59(13) . . ?
C5 C1 C7 105.91(13) . . ?
C1 C2 H2 119.2 . . ?
N1 C2 C1 121.67(14) . . ?
N1 C2 H2 119.2 . . ?
C4 C3 H3 117.4 . . ?
N1 C3 H3 117.4 . . ?
N1 C3 C4 125.25(14) . . ?
C3 C4 H4 122.8 . . ?
C5 C4 C3 114.32(15) . . ?
C5 C4 H4 122.8 . . ?
C1 C5 C4 122.84(14) . . ?
O1 C5 C1 112.16(12) . . ?
O1 C5 C4 125.00(14) . . ?
C7 C6 C11 125.04(14) . . ?
C7 C6 O1 112.14(12) . . ?
O1 C6 C11 122.82(13) . . ?
C6 C7 C1 104.94(13) . . ?
C6 C7 C8 119.55(13) . . ?
C8 C7 C1 135.50(14) . . ?
C7 C8 H8 121.3 . . ?
C9 C8 C7 117.31(14) . . ?
C9 C8 H8 121.3 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.53(14) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.60(14) . . ?
C11 C10 H10 118.7 . . ?
C6 C11 C12 120.60(13) . . ?
C10 C11 C6 113.97(14) . . ?
C10 C11 C12 125.43(13) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
C11 C12 C13 115.11(12) . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.28(12) . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C15 C14 C13 120.63(15) . . ?
C19 C14 C13 120.98(16) . . ?
C19 C14 C15 118.37(15) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.48(15) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.59(16) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.25(15) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.09(15) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.21(15) . . ?
C18 C19 H19 119.4 . . ?
C2 N1 C3 118.33(13) . . ?
C5 O1 C6 104.83(11) . . ?

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
C1 C2 N1 C3 0.9(2) . . . . ?
C1 C5 O1 C6 -1.37(16) . . . . ?
C1 C7 C8 C9 -177.73(16) . . . . ?
C2 C1 C5 C4 0.7(2) . . . . ?
C2 C1 C5 O1 179.92(13) . . . . ?
C2 C1 C7 C6 -178.67(17) . . . . ?
C2 C1 C7 C8 -0.3(3) . . . . ?
C3 C4 C5 C1 -0.1(2) . . . . ?
C3 C4 C5 O1 -179.15(14) . . . . ?
C4 C3 N1 C2 -0.1(2) . . . . ?
C4 C5 O1 C6 177.80(15) . . . . ?
C5 C1 C2 N1 -1.1(2) . . . . ?
C5 C1 C7 C6 0.56(16) . . . . ?
C5 C1 C7 C8 178.89(17) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
C6 C11 C12 C13 179.56(14) . . . . ?
C7 C1 C2 N1 178.02(16) . . . . ?
C7 C1 C5 C4 -178.67(14) . . . . ?
C7 C1 C5 O1 0.52(17) . . . . ?
C7 C6 C11 C10 0.3(2) . . . . ?
C7 C6 C11 C12 179.91(14) . . . . ?
C7 C6 O1 C5 1.76(16) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C9 C10 C11 C6 0.4(2) . . . . ?
C9 C10 C11 C12 -179.15(14) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C6 C7 C1 177.91(14) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C11 C6 O1 C5 -177.62(14) . . . . ?
C11 C12 C13 C14 179.35(13) . . . . ?
C12 C13 C14 C15 -80.01(18) . . . . ?
C12 C13 C14 C19 98.31(17) . . . . ?
C13 C14 C15 C16 177.77(13) . . . . ?
C13 C14 C19 C18 -178.42(13) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C14 C19 C18 -0.1(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C19 C14 C15 C16 -0.6(2) . . . . ?
N1 C3 C4 C5 -0.3(2) . . . . ?
O1 C6 C7 C1 -1.45(16) . . . . ?
O1 C6 C7 C8 179.89(13) . . . . ?
O1 C6 C11 C10 179.61(13) . . . . ?
O1 C6 C11 C12 -0.8(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-443
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.909
_oxdiff_exptl_absorpt_empirical_full_min 0.177
####################################################################### 
# 
# 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_2022acc0026_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2211708'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-10-07 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-10-07
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 F N O'
_chemical_formula_sum            'C24 H18 F N O'
_chemical_formula_weight         355.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H12 N1 O1 F1'
_chemical_oxdiff_usercomment     RAK-429
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'
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/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                   5.6809(2)
_cell_length_b                   13.8095(5)
_cell_length_c                   21.8999(9)
_cell_angle_alpha                90
_cell_angle_beta                 91.229(3)
_cell_angle_gamma                90
_cell_volume                     1717.66(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12241
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3040
_cell_measurement_theta_min      3.6930
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.873
_exptl_absorpt_coefficient_mu    0.732
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.755
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0195
0 0 -1 0.0078
-4 0 1 0.0779
4 0 -1 0.1012
0 1 0 0.1032
0 -1 0 0.0860
3 -5 0 0.0912

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_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
-0.0002 0.0012 0.9986 -0.0329 -0.0619 0.0045
0.0002 -0.0012 -0.9986 0.0329 0.0619 -0.0045
-3.9979 -0.0069 0.9433 0.0314 0.0105 1.0839
3.9979 0.0069 -0.9433 -0.0314 -0.0105 -1.0839
-0.0001 1.0000 -0.0033 0.0984 -0.0525 -0.0024
0.0001 -1.0000 0.0033 -0.0984 0.0525 0.0024
2.9987 -4.9940 0.0580 -0.5404 0.2081 -0.7977

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.633
_diffrn_reflns_theta_min         3.784
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -25.00   0.50    0.82    --  -45.20 138.00-177.00  146
  2  ω     20.00  98.00   0.50    0.82    --   45.20-138.00 120.00  156
  3  ω     15.00  93.00   0.50    0.82    --   45.20-132.00 -62.00  156
  4  ω   -107.00 -25.00   0.50    3.28    --  -97.00 138.00-177.00  164
  5  ω   -103.00 -25.00   0.50    3.28    --  -97.00 132.00   6.00  156
  6  ω   -164.00 -90.00   0.50    3.28    --  -97.00-132.00 -62.00  148
  7  ω   -160.00 -87.00   0.50    3.28    --  -97.00-138.00 120.00  146
  8  ω     82.00 161.00   0.50    3.28    --  109.75 138.00-177.00  158
  9  ω     85.00 165.00   0.50    3.28    --  109.75 132.00   6.00  160
 10  ω     37.00 107.00   0.50    3.28    --  109.75-138.00 120.00  140
 11  ω    -62.00 -34.00   0.50    0.82    --  -45.20 -55.00 125.87   56
 12  ω    -93.00 -21.00   0.50    0.82    --  -45.20 132.00   6.00  144
 13  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -60.00 -59.83   58
 14  ω   -119.00 -35.00   0.50    0.82    --  -45.20 -54.00-128.94  168
 15  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -60.00 -30.04   58
 16  ω    -23.00  30.00   0.50    0.82    --  -45.20  38.00  30.00  106
 17  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -59.00  96.92   58
 18  ω    -30.00  15.00   0.50    0.82    --   45.20 -38.00  90.00   90
 19  ω    -30.00  15.00   0.50    0.82    --   45.20 -38.00  30.00   90
 20  ω    -30.00  15.00   0.50    0.82    --   45.20 -38.00   0.00   90
 21  ω    -30.00  15.00   0.50    0.82    --   45.20 -38.00  60.00   90
 22  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00  30.00   64
 23  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00  90.00   64
 24  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00-150.00   64
 25  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00 150.00   64
 26  ω   -140.00 -90.00   0.50    3.28    --  -97.00 -15.00-180.00  100
 27  ω   -170.00-106.00   0.50    3.28    --  -97.00 -77.00  30.00  128
 28  ω   -140.00 -90.00   0.50    3.28    --  -97.00 -15.00   0.00  100
 29  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00 -30.00   64
 30  ω    -93.00 -23.00   0.50    3.28    --  -97.00  93.00  23.27  140
 31  ω    -55.00 -23.00   0.50    3.28    --  -97.00  61.00   0.00   64
 32  ω    -93.00 -23.00   0.50    3.28    --  -97.00  93.00-105.50  140
 33  ω   -140.00 -90.00   0.50    3.28    --  -97.00 -15.00 -60.00  100
 34  ω    -93.00 -25.00   0.50    3.28    --  -97.00  97.00-138.11  136
 35  ω   -170.00-106.00   0.50    3.28    --  -97.00 -77.00-150.00  128
 36  ω    104.00 132.00   0.50    3.28    --  109.75  15.00 150.00   56
 37  ω    104.00 132.00   0.50    3.28    --  109.75  15.00 -30.00   56
 38  ω    104.00 132.00   0.50    3.28    --  109.75  15.00 120.00   56
 39  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00-150.00  112
 40  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00 -60.00  112
 41  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00   0.00  112
 42  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00 150.00  112
 43  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00-180.00  112
 44  ω    104.00 132.00   0.50    3.28    --  109.75  15.00-180.00   56
 45  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00 -30.00  112
 46  ω     39.00 100.00   0.50    3.28    --  109.75-125.00 150.00  122
 47  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00 120.00  112
 48  ω     37.00  71.00   0.50    3.28    --  109.75 -77.00 -90.00   68
 49  ω    104.00 162.00   0.50    3.28    --  109.75  30.00-150.00  116
 50  ω     37.00  93.00   0.50    3.28    --  109.75 -95.00  30.00  112
 51  ω    104.00 132.00   0.50    3.28    --  109.75  15.00 -60.00   56
 52  ω     38.00 103.00   0.50    3.28    --  109.75-132.00 -62.00  130
 53  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -60.00  13.64   58
 54  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -58.00  65.23   58
 55  ω    -62.00 -34.00   0.50    0.82    --  -45.20 -57.00 168.54   56
 56  ω   -118.00 -48.00   0.50    0.82    --  -45.20 -49.00  58.26  140
 57  ω    -62.00 -33.00   0.50    0.82    --  -45.20 -59.00  38.51   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0158251000
_diffrn_orient_matrix_UB_12      0.0983332000
_diffrn_orient_matrix_UB_13      -0.0330821000
_diffrn_orient_matrix_UB_21      -0.0171650000
_diffrn_orient_matrix_UB_22      -0.0526960000
_diffrn_orient_matrix_UB_23      -0.0619740000
_diffrn_orient_matrix_UB_31      -0.2700562000
_diffrn_orient_matrix_UB_32      -0.0023661000
_diffrn_orient_matrix_UB_33      0.0044398000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3311
_reflns_number_total             3518
_reflns_special_details          
;
 _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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.670
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3518
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1488
_refine_ls_R_factor_gt           0.1448
_refine_ls_restrained_S_all      1.091
_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)+(0.1701P)²+12.0581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4312
_refine_ls_wR_factor_ref         0.4329
_refine_special_details          
'Refined against HKLF 5 data (generated in Platon using -1 0 0 0 -1 0 0.165 0 1),Twin'
_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:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C13(H13), C14(H14), C17(H17),
 C18(H18), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
C1 C -0.5858(13) 0.7010(5) 0.4727(3) 0.0310(16) Uani 1 1 d . . . . .
C2 C -0.3980(14) 0.6457(5) 0.4547(3) 0.0342(16) Uani 1 1 d . . . . .
H2 H -0.379773 0.627680 0.413165 0.041 Uiso 1 1 calc R U . . .
C3 C -0.2372(14) 0.6174(6) 0.4994(4) 0.0358(17) Uani 1 1 d . . . . .
H3 H -0.105664 0.579541 0.487997 0.043 Uiso 1 1 calc R U . . .
C4 C -0.2609(13) 0.6424(5) 0.5602(3) 0.0326(16) Uani 1 1 d . . . . .
C5 C -0.4554(14) 0.6995(5) 0.5757(3) 0.0345(17) Uani 1 1 d . . . . .
H5 H -0.475795 0.717786 0.617027 0.041 Uiso 1 1 calc R U . . .
C6 C -0.6185(14) 0.7298(5) 0.5314(3) 0.0331(16) Uani 1 1 d . . . . .
H6 H -0.748522 0.769366 0.541808 0.040 Uiso 1 1 calc R U . . .
C7 C -0.0910(15) 0.6054(6) 0.6087(4) 0.0400(19) Uani 1 1 d . . . . .
H7A H -0.091311 0.649792 0.644183 0.048 Uiso 1 1 calc R U . . .
H7B H 0.069983 0.604619 0.592300 0.048 Uiso 1 1 calc R U . . .
C8 C -0.1553(13) 0.5046(5) 0.6294(3) 0.0312(15) Uani 1 1 d . . . . .
H8A H -0.153441 0.461327 0.593413 0.037 Uiso 1 1 calc R U . . .
H8B H -0.318988 0.506294 0.644006 0.037 Uiso 1 1 calc R U . . .
C9 C -0.0007(13) 0.4596(5) 0.6793(3) 0.0291(15) Uani 1 1 d . . . . .
C10 C 0.1966(13) 0.5028(5) 0.7031(3) 0.0297(15) Uani 1 1 d . . . . .
H10 H 0.249767 0.561999 0.686148 0.036 Uiso 1 1 calc R U . . .
C11 C 0.3242(12) 0.4606(5) 0.7529(3) 0.0262(14) Uani 1 1 d . . . . .
C12 C 0.2438(13) 0.3713(5) 0.7786(3) 0.0286(15) Uani 1 1 d . . . . .
C13 C 0.0422(13) 0.3259(5) 0.7509(3) 0.0317(16) Uani 1 1 d . . . . .
H13 H -0.010979 0.265228 0.765792 0.038 Uiso 1 1 calc R U . . .
C14 C -0.0747(13) 0.3698(5) 0.7028(3) 0.0310(15) Uani 1 1 d . . . . .
H14 H -0.208795 0.338851 0.684964 0.037 Uiso 1 1 calc R U . . .
C15 C 0.5225(12) 0.4995(5) 0.7827(3) 0.0279(14) Uani 1 1 d . . . . .
C16 C 0.6231(12) 0.4568(5) 0.8336(3) 0.0268(14) Uani 1 1 d . . . . .
C17 C 0.5284(12) 0.3704(5) 0.8555(3) 0.0299(15) Uani 1 1 d . . . . .
H17 H 0.598142 0.341532 0.890832 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9933(13) 0.5182(5) 0.8976(3) 0.0304(15) Uani 1 1 d . . . . .
H18 H 0.995652 0.468185 0.927336 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8212(12) 0.5188(5) 0.8511(3) 0.0276(14) Uani 1 1 d . . . . .
C20 C 0.8227(13) 0.5927(5) 0.8077(3) 0.0292(15) Uani 1 1 d . . . . .
C21 C 0.9920(12) 0.6638(5) 0.8064(3) 0.0298(15) Uani 1 1 d . . . . .
H21 H 0.994040 0.711461 0.775116 0.036 Uiso 1 1 calc R U . . .
C22 C 1.1594(13) 0.6616(5) 0.8533(3) 0.0315(16) Uani 1 1 d . . . . .
H22 H 1.278827 0.709746 0.854151 0.038 Uiso 1 1 calc R U . . .
C23 C 1.1602(13) 0.5909(5) 0.8999(3) 0.0306(15) Uani 1 1 d . . . . .
C24 C 1.3404(14) 0.5963(6) 0.9509(4) 0.0382(18) Uani 1 1 d . . . . .
H24A H 1.296547 0.647349 0.979543 0.057 Uiso 1 1 calc R U . . .
H24B H 1.494943 0.610921 0.934118 0.057 Uiso 1 1 calc R U . . .
H24C H 1.347382 0.533989 0.972311 0.057 Uiso 1 1 calc R U . . .
F1 F -0.7476(8) 0.7283(3) 0.4291(2) 0.0400(12) Uani 1 1 d . . . . .
N1 N 0.3442(11) 0.3268(4) 0.8287(3) 0.0304(13) Uani 1 1 d . . . . .
O1 O 0.6380(8) 0.5815(3) 0.7652(2) 0.0278(11) Uani 1 1 d . . . . .


_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
C1 C2 1.377(11) . ?
C1 C6 1.363(10) . ?
C1 F1 1.364(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.386(11) . ?
C4 C5 1.405(11) . ?
C4 C7 1.508(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(11) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.511(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.520(10) . ?
C9 C10 1.363(10) . ?
C9 C14 1.411(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.421(10) . ?
C11 C12 1.434(9) . ?
C11 C15 1.397(10) . ?
C12 C13 1.429(10) . ?
C12 N1 1.371(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.376(10) . ?
C15 O1 1.367(8) . ?
C16 C17 1.398(10) . ?
C16 C19 1.459(10) . ?
C17 H17 0.9500 . ?
C17 N1 1.332(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.396(10) . ?
C18 C23 1.381(11) . ?
C19 C20 1.394(10) . ?
C20 C21 1.375(10) . ?
C20 O1 1.397(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(10) . ?
C22 H22 0.9500 . ?
C22 C23 1.412(10) . ?
C23 C24 1.501(10) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C6 C1 C2 123.7(7) . . ?
C6 C1 F1 118.4(7) . . ?
F1 C1 C2 117.9(7) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.3(7) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.4(7) . . ?
C4 C3 H3 118.8 . . ?
C3 C4 C5 117.6(7) . . ?
C3 C4 C7 121.2(7) . . ?
C5 C4 C7 121.1(7) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.2(7) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 117.9(7) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C4 C7 H7A 109.3 . . ?
C4 C7 H7B 109.3 . . ?
C4 C7 C8 111.6(6) . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C7 C8 C9 116.9(6) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.1 . . ?
C9 C8 H8B 108.1 . . ?
C10 C9 C8 123.6(6) . . ?
C10 C9 C14 119.6(7) . . ?
C14 C9 C8 116.7(6) . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.0(7) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 119.5(6) . . ?
C15 C11 C10 126.3(6) . . ?
C15 C11 C12 114.1(6) . . ?
C13 C12 C11 118.1(6) . . ?
N1 C12 C11 124.7(6) . . ?
N1 C12 C13 117.3(6) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.1(7) . . ?
C14 C13 H13 120.0 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.7(7) . . ?
C13 C14 H14 119.2 . . ?
C16 C15 C11 122.0(6) . . ?
O1 C15 C11 125.1(6) . . ?
O1 C15 C16 112.9(6) . . ?
C15 C16 C17 119.2(7) . . ?
C15 C16 C19 105.4(6) . . ?
C17 C16 C19 135.4(7) . . ?
C16 C17 H17 118.7 . . ?
N1 C17 C16 122.7(7) . . ?
N1 C17 H17 118.7 . . ?
C19 C18 H18 120.3 . . ?
C23 C18 H18 120.3 . . ?
C23 C18 C19 119.5(7) . . ?
C18 C19 C16 135.4(7) . . ?
C20 C19 C16 105.5(6) . . ?
C20 C19 C18 119.1(7) . . ?
C19 C20 O1 110.9(6) . . ?
C21 C20 C19 123.5(7) . . ?
C21 C20 O1 125.5(6) . . ?
C20 C21 H21 122.0 . . ?
C20 C21 C22 115.9(7) . . ?
C22 C21 H21 122.0 . . ?
C21 C22 H22 118.6 . . ?
C21 C22 C23 122.9(7) . . ?
C23 C22 H22 118.6 . . ?
C18 C23 C22 119.0(7) . . ?
C18 C23 C24 121.3(7) . . ?
C22 C23 C24 119.7(7) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 N1 C12 117.3(6) . . ?
C15 O1 C20 105.3(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
C1 C2 C3 C4 0.4(11) . . . . ?
C2 C1 C6 C5 -1.6(11) . . . . ?
C2 C3 C4 C5 -0.8(11) . . . . ?
C2 C3 C4 C7 176.1(7) . . . . ?
C3 C4 C5 C6 0.1(11) . . . . ?
C3 C4 C7 C8 -82.6(9) . . . . ?
C4 C5 C6 C1 1.0(11) . . . . ?
C4 C7 C8 C9 -178.7(6) . . . . ?
C5 C4 C7 C8 94.2(9) . . . . ?
C6 C1 C2 C3 0.9(11) . . . . ?
C7 C4 C5 C6 -176.9(7) . . . . ?
C7 C8 C9 C10 -3.9(11) . . . . ?
C7 C8 C9 C14 173.8(7) . . . . ?
C8 C9 C10 C11 175.2(6) . . . . ?
C8 C9 C14 C13 -175.3(7) . . . . ?
C9 C10 C11 C12 -0.1(10) . . . . ?
C9 C10 C11 C15 -177.3(7) . . . . ?
C10 C9 C14 C13 2.5(11) . . . . ?
C10 C11 C12 C13 2.7(10) . . . . ?
C10 C11 C12 N1 -176.1(7) . . . . ?
C10 C11 C15 C16 174.8(7) . . . . ?
C10 C11 C15 O1 -5.7(11) . . . . ?
C11 C12 C13 C14 -2.8(10) . . . . ?
C11 C12 N1 C17 0.6(10) . . . . ?
C11 C15 C16 C17 1.8(10) . . . . ?
C11 C15 C16 C19 -179.4(6) . . . . ?
C11 C15 O1 C20 179.9(6) . . . . ?
C12 C11 C15 C16 -2.5(10) . . . . ?
C12 C11 C15 O1 176.9(6) . . . . ?
C12 C13 C14 C9 0.2(11) . . . . ?
C13 C12 N1 C17 -178.3(6) . . . . ?
C14 C9 C10 C11 -2.5(10) . . . . ?
C15 C11 C12 C13 -179.7(6) . . . . ?
C15 C11 C12 N1 1.4(10) . . . . ?
C15 C16 C17 N1 0.4(11) . . . . ?
C15 C16 C19 C18 179.7(8) . . . . ?
C15 C16 C19 C20 -1.1(7) . . . . ?
C16 C15 O1 C20 -0.5(8) . . . . ?
C16 C17 N1 C12 -1.5(10) . . . . ?
C16 C19 C20 C21 -176.4(7) . . . . ?
C16 C19 C20 O1 0.8(7) . . . . ?
C17 C16 C19 C18 -1.8(14) . . . . ?
C17 C16 C19 C20 177.4(8) . . . . ?
C18 C19 C20 C21 2.9(11) . . . . ?
C18 C19 C20 O1 -179.8(6) . . . . ?
C19 C16 C17 N1 -177.9(7) . . . . ?
C19 C18 C23 C22 -3.1(10) . . . . ?
C19 C18 C23 C24 176.6(7) . . . . ?
C19 C20 C21 C22 -3.3(11) . . . . ?
C19 C20 O1 C15 -0.2(7) . . . . ?
C20 C21 C22 C23 0.4(11) . . . . ?
C21 C20 O1 C15 177.0(7) . . . . ?
C21 C22 C23 C18 2.7(11) . . . . ?
C21 C22 C23 C24 -177.0(7) . . . . ?
C23 C18 C19 C16 179.6(7) . . . . ?
C23 C18 C19 C20 0.4(10) . . . . ?
F1 C1 C2 C3 -179.1(6) . . . . ?
F1 C1 C6 C5 178.5(6) . . . . ?
N1 C12 C13 C14 176.2(7) . . . . ?
O1 C15 C16 C17 -177.8(6) . . . . ?
O1 C15 C16 C19 1.0(8) . . . . ?
O1 C20 C21 C22 179.9(6) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-429
_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 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.608
####################################################################### 
# 
# 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_2022acc0024_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2204946'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H21 N O3'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     RAK-441
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'
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                   19.3497(7)
_cell_length_b                   7.1784(2)
_cell_length_c                   12.8947(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.665(4)
_cell_angle_gamma                90
_cell_volume                     1740.37(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5813
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.0830
_cell_measurement_theta_min      4.6710
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.920
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_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
5 0 -1 0.0490
-5 0 1 0.0118
-1 -5 0 0.0283
0 0 1 0.0566
0 0 -1 0.0566
-2 5 1 0.0546
2 -5 0 0.0293

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_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
4.9897 0.0028 -0.9936 -0.0942 -0.3796 0.0732
-4.9897 -0.0028 0.9936 0.0942 0.3796 -0.0732
-0.8402 -4.9874 0.0033 0.0177 0.2658 1.0392
-0.0063 -0.0010 0.9998 0.1210 -0.0209 0.0017
0.0063 0.0010 -0.9998 -0.1210 0.0209 -0.0017
-2.1561 4.9853 0.9927 0.0872 -0.0464 -1.0825
2.1498 -4.9863 0.0070 0.0338 0.0255 1.0842

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10678
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.710
_diffrn_reflns_theta_min         4.704
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -28.00   0.50    2.00    --  -97.00  77.00-180.00   58
  2  ω    -51.00 -25.00   0.50    2.00    --  -97.00  61.00-180.00   52
  3  ω    -55.00 -29.00   0.50    2.00    --  -97.00  61.00 -90.00   52
  4  ω    -50.00 -23.00   0.50    2.00    --  -97.00  61.00 -60.00   54
  5  ω    -52.00 -23.00   0.50    2.00    --  -97.00  61.00 -30.00   58
  6  ω    -55.00 -29.00   0.50    2.00    --  -97.00  61.00  60.00   52
  7  ω    -55.00 -29.00   0.50    2.00    --  -97.00  61.00  90.00   52
  8  ω    -55.00 -25.00   0.50    2.00    --  -97.00  61.00 120.00   60
  9  ω    -23.00  30.00   0.50    0.81    --  -45.09  38.00 120.00  106
 10  ω   -118.00 -43.00   0.50    0.81    --  -45.09 -12.00 177.00  150
 11  ω   -120.00 -95.00   0.50    2.00    --  -97.00 -12.00 177.00   50
 12  ω   -132.00 -98.00   0.50    2.00    --  -97.00 -15.00-120.00   68
 13  ω    -88.00 -49.00   0.50    0.81    --  -45.09 125.00 -60.00   78
 14  ω     44.00 112.00   0.50    0.81    --   45.09  12.00 -10.00  136
 15  ω    110.00 159.00   0.50    2.00    --  109.75  30.00-150.00   98
 16  ω    104.00 130.00   0.50    2.00    --  109.75  15.00 -60.00   52
 17  ω    105.00 130.00   0.50    2.00    --  109.75  15.00-180.00   50
 18  ω    104.00 131.00   0.50    2.00    --  109.75  15.00 -90.00   54
 19  ω    116.00 162.00   0.50    2.00    --  109.75  30.00 -30.00   92
 20  ω    106.00 132.00   0.50    2.00    --  109.75  15.00  30.00   52
 21  ω    106.00 132.00   0.50    2.00    --  109.75  15.00 150.00   52
 22  ω     69.00  95.00   0.50    2.00    --  109.75-125.00 150.00   52
 23  ω     42.00  96.00   0.50    2.00    --  109.75-125.00  90.00  108
 24  ω     61.00  87.00   0.50    2.00    --  109.75 -95.00 120.00   52
 25  ω     51.00  89.00   0.50    2.00    --  109.75 -95.00 150.00   76
 26  ω     37.00  69.00   0.50    2.00    --  109.75 -77.00  90.00   64
 27  ω     60.00  93.00   0.50    2.00    --  109.75 -95.00  60.00   66
 28  ω    -27.00   3.00   0.50    0.81    --   45.09 -38.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0052240000
_diffrn_orient_matrix_UB_12      -0.0043502000
_diffrn_orient_matrix_UB_13      0.1210721000
_diffrn_orient_matrix_UB_21      -0.0803253000
_diffrn_orient_matrix_UB_22      -0.0397840000
_diffrn_orient_matrix_UB_23      -0.0214454000
_diffrn_orient_matrix_UB_31      0.0151069000
_diffrn_orient_matrix_UB_32      -0.2109172000
_diffrn_orient_matrix_UB_33      0.0016037000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2955
_reflns_number_total             3488
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.096
_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)+(0.0856P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1391
_refine_ls_wR_factor_ref         0.1443
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C13(H13), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_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
C1 C 0.91186(8) 0.6721(2) 0.61483(13) 0.0287(3) Uani 1 1 d . . . . .
C2 C 0.95888(9) 0.6472(2) 0.72614(14) 0.0333(4) Uani 1 1 d . . . . .
H2A H 0.961159 0.764624 0.765618 0.050 Uiso 1 1 calc R U . . .
H2B H 1.006839 0.611400 0.721064 0.050 Uiso 1 1 calc R U . . .
H2C H 0.939007 0.549627 0.763631 0.050 Uiso 1 1 calc R U . . .
C3 C 0.93617(9) 0.8300(2) 0.55296(14) 0.0341(4) Uani 1 1 d . . . . .
H3A H 0.904255 0.838571 0.481753 0.051 Uiso 1 1 calc R U . . .
H3B H 0.984729 0.805306 0.546212 0.051 Uiso 1 1 calc R U . . .
H3C H 0.935178 0.947673 0.591107 0.051 Uiso 1 1 calc R U . . .
C4 C 0.90664(9) 0.4912(2) 0.55217(15) 0.0374(4) Uani 1 1 d . . . . .
H4A H 0.887932 0.392755 0.590596 0.056 Uiso 1 1 calc R U . . .
H4B H 0.953960 0.455652 0.543949 0.056 Uiso 1 1 calc R U . . .
H4C H 0.874674 0.508465 0.481590 0.056 Uiso 1 1 calc R U . . .
C5 C 0.82023(8) 0.8484(2) 0.67621(12) 0.0273(3) Uani 1 1 d . . . . .
C6 C 0.74249(8) 0.8448(2) 0.67770(12) 0.0264(3) Uani 1 1 d . . . . .
H6A H 0.721043 0.725766 0.647208 0.032 Uiso 1 1 calc R U . . .
H6B H 0.717327 0.947700 0.633180 0.032 Uiso 1 1 calc R U . . .
C7 C 0.73378(8) 0.8655(2) 0.79181(12) 0.0264(3) Uani 1 1 d . . . . .
H7A H 0.758251 0.760010 0.834757 0.032 Uiso 1 1 calc R U . . .
H7B H 0.757928 0.981404 0.822498 0.032 Uiso 1 1 calc R U . . .
C8 C 0.65756(8) 0.87140(18) 0.80260(12) 0.0243(3) Uani 1 1 d . . . . .
C9 C 0.64720(8) 0.8780(2) 0.90747(12) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.687745 0.879577 0.965799 0.032 Uiso 1 1 calc R U . . .
C10 C 0.58050(8) 0.8822(2) 0.92838(12) 0.0272(3) Uani 1 1 d . . . . .
H10 H 0.574159 0.887215 0.999168 0.033 Uiso 1 1 calc R U . . .
C11 C 0.52349(8) 0.87856(19) 0.84073(12) 0.0239(3) Uani 1 1 d . . . . .
C12 C 0.53056(8) 0.87508(18) 0.73526(11) 0.0228(3) Uani 1 1 d . . . . .
C13 C 0.59906(8) 0.87166(18) 0.71636(11) 0.0236(3) Uani 1 1 d . . . . .
H13 H 0.605278 0.869554 0.645460 0.028 Uiso 1 1 calc R U . . .
C14 C 0.45818(8) 0.87276(18) 0.67035(12) 0.0237(3) Uani 1 1 d . . . . .
C15 C 0.41469(8) 0.87413(18) 0.74131(12) 0.0241(3) Uani 1 1 d . . . . .
C16 C 0.34010(8) 0.86835(18) 0.70899(12) 0.0238(3) Uani 1 1 d . . . . .
C17 C 0.31281(8) 0.86553(19) 0.59630(12) 0.0250(3) Uani 1 1 d . . . . .
C18 C 0.42453(8) 0.86874(19) 0.56019(12) 0.0256(3) Uani 1 1 d . . . . .
H18 H 0.453543 0.867904 0.510152 0.031 Uiso 1 1 calc R U . . .
C19 C 0.29387(8) 0.86150(19) 0.77892(13) 0.0273(3) Uani 1 1 d . . . . .
H19 H 0.312540 0.861942 0.854002 0.033 Uiso 1 1 calc R U . . .
C20 C 0.22175(9) 0.8542(2) 0.73741(13) 0.0291(3) Uani 1 1 d . . . . .
H20 H 0.190388 0.850104 0.784013 0.035 Uiso 1 1 calc R U . . .
C21 C 0.19400(9) 0.8528(2) 0.62627(13) 0.0294(3) Uani 1 1 d . . . . .
H21 H 0.143956 0.848369 0.598646 0.035 Uiso 1 1 calc R U . . .
C22 C 0.23819(8) 0.8576(2) 0.55695(13) 0.0283(3) Uani 1 1 d . . . . .
H22 H 0.218436 0.855694 0.482146 0.034 Uiso 1 1 calc R U . . .
N1 N 0.35516(7) 0.86611(16) 0.52387(10) 0.0264(3) Uani 1 1 d . . . . .
O1 O 0.83736(5) 0.70361(15) 0.62091(8) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.86133(6) 0.96715(16) 0.71930(10) 0.0369(3) Uani 1 1 d . . . . .
O3 O 0.45250(6) 0.87873(14) 0.84542(8) 0.0261(3) Uani 1 1 d . . . . .


_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
C1 C2 1.518(2) . ?
C1 C3 1.523(2) . ?
C1 C4 1.521(2) . ?
C1 O1 1.4793(17) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.509(2) . ?
C5 O1 1.3453(18) . ?
C5 O2 1.2081(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.514(2) . ?
C8 C9 1.414(2) . ?
C8 C13 1.387(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(2) . ?
C11 C12 1.3989(19) . ?
C11 O3 1.3893(18) . ?
C12 C13 1.403(2) . ?
C12 C14 1.452(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.382(2) . ?
C14 C18 1.416(2) . ?
C15 C16 1.405(2) . ?
C15 O3 1.3691(17) . ?
C16 C17 1.424(2) . ?
C16 C19 1.413(2) . ?
C17 C22 1.414(2) . ?
C17 N1 1.3804(19) . ?
C18 H18 0.9500 . ?
C18 N1 1.313(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.372(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.407(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.376(2) . ?
C22 H22 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C3 113.13(13) . . ?
C2 C1 C4 110.59(13) . . ?
C4 C1 C3 110.32(13) . . ?
O1 C1 C2 109.99(12) . . ?
O1 C1 C3 109.86(12) . . ?
O1 C1 C4 102.44(12) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 111.40(12) . . ?
O2 C5 C6 123.78(13) . . ?
O2 C5 O1 124.83(14) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C5 C6 C7 110.36(13) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C8 C7 C6 115.01(13) . . ?
C8 C7 H7A 108.5 . . ?
C8 C7 H7B 108.5 . . ?
C9 C8 C7 116.74(13) . . ?
C13 C8 C7 123.67(13) . . ?
C13 C8 C9 119.58(14) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 C8 122.56(14) . . ?
C10 C9 H9 118.7 . . ?
C9 C10 H10 121.9 . . ?
C9 C10 C11 116.29(14) . . ?
C11 C10 H10 121.9 . . ?
C10 C11 C12 123.61(14) . . ?
C10 C11 O3 124.85(13) . . ?
O3 C11 C12 111.55(13) . . ?
C11 C12 C13 118.85(14) . . ?
C11 C12 C14 104.95(12) . . ?
C13 C12 C14 136.20(13) . . ?
C8 C13 C12 119.09(13) . . ?
C8 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C15 C14 C12 105.88(13) . . ?
C15 C14 C18 117.19(14) . . ?
C18 C14 C12 136.93(14) . . ?
C14 C15 C16 123.15(14) . . ?
O3 C15 C14 112.44(13) . . ?
O3 C15 C16 124.40(13) . . ?
C15 C16 C17 114.23(13) . . ?
C15 C16 C19 124.92(14) . . ?
C19 C16 C17 120.83(14) . . ?
C22 C17 C16 117.89(14) . . ?
N1 C17 C16 123.64(14) . . ?
N1 C17 C22 118.45(14) . . ?
C14 C18 H18 118.4 . . ?
N1 C18 C14 123.15(14) . . ?
N1 C18 H18 118.4 . . ?
C16 C19 H19 120.3 . . ?
C20 C19 C16 119.41(15) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.39(15) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.5 . . ?
C22 C21 C20 121.03(15) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.44(15) . . ?
C21 C22 H22 119.8 . . ?
C18 N1 C17 118.62(13) . . ?
C5 O1 C1 120.74(11) . . ?
C15 O3 C11 105.19(11) . . ?

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
C2 C1 O1 C5 58.89(17) . . . . ?
C3 C1 O1 C5 -66.26(17) . . . . ?
C4 C1 O1 C5 176.50(13) . . . . ?
C5 C6 C7 C8 177.71(11) . . . . ?
C6 C5 O1 C1 -175.99(12) . . . . ?
C6 C7 C8 C9 175.93(12) . . . . ?
C6 C7 C8 C13 -4.42(19) . . . . ?
C7 C8 C9 C10 -179.42(13) . . . . ?
C7 C8 C13 C12 179.22(12) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C8 C13 C12 -1.14(19) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C9 C10 C11 O3 178.89(13) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C10 C11 C12 C14 -179.80(13) . . . . ?
C10 C11 O3 C15 -179.89(13) . . . . ?
C11 C12 C13 C8 0.15(19) . . . . ?
C11 C12 C14 C15 -0.27(14) . . . . ?
C11 C12 C14 C18 -179.88(16) . . . . ?
C12 C11 O3 C15 0.37(14) . . . . ?
C12 C14 C15 C16 -178.51(12) . . . . ?
C12 C14 C15 O3 0.52(15) . . . . ?
C12 C14 C18 N1 179.50(15) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
C13 C12 C14 C15 178.48(15) . . . . ?
C13 C12 C14 C18 -1.1(3) . . . . ?
C14 C12 C13 C8 -178.47(14) . . . . ?
C14 C15 C16 C17 -1.46(19) . . . . ?
C14 C15 C16 C19 177.15(13) . . . . ?
C14 C15 O3 C11 -0.56(15) . . . . ?
C14 C18 N1 C17 -0.6(2) . . . . ?
C15 C14 C18 N1 -0.1(2) . . . . ?
C15 C16 C17 C22 179.32(12) . . . . ?
C15 C16 C17 N1 0.74(19) . . . . ?
C15 C16 C19 C20 -179.29(13) . . . . ?
C16 C15 O3 C11 178.47(12) . . . . ?
C16 C17 C22 C21 0.0(2) . . . . ?
C16 C17 N1 C18 0.3(2) . . . . ?
C16 C19 C20 C21 0.3(2) . . . . ?
C17 C16 C19 C20 -0.8(2) . . . . ?
C18 C14 C15 C16 1.2(2) . . . . ?
C18 C14 C15 O3 -179.78(11) . . . . ?
C19 C16 C17 C22 0.64(19) . . . . ?
C19 C16 C17 N1 -177.94(13) . . . . ?
C19 C20 C21 C22 0.3(2) . . . . ?
C20 C21 C22 C17 -0.4(2) . . . . ?
C22 C17 N1 C18 -178.33(13) . . . . ?
N1 C17 C22 C21 178.61(13) . . . . ?
O1 C5 C6 C7 129.54(13) . . . . ?
O2 C5 C6 C7 -50.6(2) . . . . ?
O2 C5 O1 C1 4.2(2) . . . . ?
O3 C11 C12 C13 -179.07(11) . . . . ?
O3 C11 C12 C14 -0.06(15) . . . . ?
O3 C15 C16 C17 179.62(12) . . . . ?
O3 C15 C16 C19 -1.8(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-441
_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 2.598
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_2022acc0020_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2204795'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-09-01 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-01
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 O2'
_chemical_formula_sum            'C21 H18 O2'
_chemical_formula_weight         302.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12O2
_chemical_oxdiff_usercomment     'RAK-479 small vial'
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'
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                   7.6458(2)
_cell_length_b                   6.14330(10)
_cell_length_c                   66.279(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.529(2)
_cell_angle_gamma                90
_cell_volume                     3112.05(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10642
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4320
_cell_measurement_theta_min      3.9470
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1280
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0409
0 0 1 0.0175
0 -4 -3 0.1340
0 4 3 0.1340
-2 1 -5 0.0418
2 -1 5 0.0418
-2 0 -5 0.0411
3 1 5 0.1150

_exptl_crystal_recrystallization_method 
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.058
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
-0.0008 -0.0009 -1.0012 0.0011 -0.0232 0.0021
0.0008 0.0009 1.0012 -0.0011 0.0232 -0.0021
-0.0058 -4.0027 -3.0120 -0.0546 -0.1744 -0.9900
0.0058 4.0027 3.0120 0.0546 0.1744 0.9900
-2.0007 0.9957 -5.0075 0.4219 -0.0866 0.2356
2.0007 -0.9957 5.0075 -0.4219 0.0866 -0.2356
-2.0016 -0.0043 -5.0096 0.4074 -0.1129 -0.0135
3.0015 1.0041 5.0137 -0.5940 0.1376 0.2746

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1228
_diffrn_reflns_av_unetI/netI     0.0588
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       78
_diffrn_reflns_limit_l_min       -78
_diffrn_reflns_number            30515
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        66.497
_diffrn_reflns_theta_max         66.497
_diffrn_reflns_theta_min         3.335
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00 121.08   0.38    0.26    --   45.09  19.00  90.00  216
  2  ω    104.00 130.98   0.38    1.05    --  109.75  15.00 150.00   71
  3  ω    104.00 130.98   0.38    1.05    --  109.75  15.00 120.00   71
  4  ω    104.00 130.98   0.38    1.05    --  109.75  15.00  60.00   71
  5  ω    104.00 130.98   0.38    1.05    --  109.75  15.00  30.00   71
  6  ω    104.00 130.98   0.38    1.05    --  109.75  15.00   0.00   71
  7  ω     37.00  70.06   0.38    1.05    --  109.75 -77.00  90.00   87
  8  ω     37.00  91.72   0.38    1.05    --  109.75 -95.00  90.00  144
  9  ω    -30.00  14.08   0.38    0.26    --   45.09 -38.00 150.00  116
 10  ω    -30.00  14.08   0.38    0.26    --   45.09 -38.00 120.00  116
 11  ω    -30.00  14.08   0.38    0.26    --   45.09 -38.00  90.00  116
 12  ω     37.00  70.06   0.38    1.05    --  109.75 -77.00-120.00   87
 13  ω    -30.00  14.08   0.38    0.26    --   45.09 -38.00-120.00  116
 14  ω   -117.00 -36.82   0.38    0.26    --  -45.09 -50.00-179.15  211
 15  ω    -62.00 -33.88   0.38    0.26    --  -45.09 -59.00-140.84   74
 16  ω    -62.00 -33.88   0.38    0.26    --  -45.09 -58.00 -79.36   74
 17  ω    -62.00 -32.74   0.38    0.26    --  -45.09 -61.00  87.48   77
 18  ω    -62.00 -34.64   0.38    0.26    --  -45.09 -56.00 120.36   72
 19  ω    -93.00 -23.84   0.38    1.05    --  -97.00  93.00  64.16  182
 20  ω   -100.00 -26.66   0.38    1.05    --  -97.00 125.00   0.00  193
 21  ω    -93.00 -26.12   0.38    1.05    --  -97.00  97.00   4.80  176
 22  ω    -93.00 -26.12   0.38    1.05    --  -97.00 104.00  92.08  176
 23  ω    -49.00  27.00   0.38    0.26    --  -45.09  57.00 120.00  200
 24  ω    -55.00 -23.84   0.38    1.05    --  -97.00  61.00 150.00   82
 25  ω    -55.00 -23.84   0.38    1.05    --  -97.00  61.00   0.00   82
 26  ω    -79.00 -24.28   0.38    1.05    --  -97.00  77.00 -60.00  144
 27  ω    -55.00 -29.92   0.38    1.05    --  -97.00  61.00-120.00   66
 28  ω    -55.00 -23.84   0.38    1.05    --  -97.00  61.00-150.00   82
 29  ω   -140.00 -90.98   0.38    1.05    --  -97.00 -15.00-150.00  129
 30  ω   -140.00 -90.98   0.38    1.05    --  -97.00 -15.00-180.00  129
 31  ω   -170.00-106.92   0.38    1.05    --  -97.00 -77.00-150.00  166
 32  ω   -170.00 -90.20   0.38    1.05    --  -97.00 -46.00 -52.95  210
 33  ω   -140.00 -90.98   0.38    1.05    --  -97.00 -15.00  30.00  129
 34  ω   -140.00 -90.98   0.38    1.05    --  -97.00 -15.00  60.00  129
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2012125000
_diffrn_orient_matrix_UB_12      0.0146443000
_diffrn_orient_matrix_UB_13      -0.0009502000
_diffrn_orient_matrix_UB_21      -0.0015419000
_diffrn_orient_matrix_UB_22      0.0261802000
_diffrn_orient_matrix_UB_23      0.0231205000
_diffrn_orient_matrix_UB_31      0.0120870000
_diffrn_orient_matrix_UB_32      0.2490747000
_diffrn_orient_matrix_UB_33      -0.0023446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5280
_reflns_number_total             5621
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.585
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5621
_refine_ls_number_restraints     372
_refine_ls_R_factor_all          0.1323
_refine_ls_R_factor_gt           0.1298
_refine_ls_restrained_S_all      1.055
_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)+(0.1633P)²+21.0796P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3480
_refine_ls_wR_factor_ref         0.3493
_refine_special_details          
;Refined using TWIN LAW -1 0 0, 0 -1 0, 0.5 0 1
BASF 0.3,Twin
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.693(4)
 0.307(4)
2. 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
3. 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
4.a Secondary CH2 refined with riding coordinates:
 C108(H10D,H10E), C109(H10F,H10G), C208(H20D,H20E), C209(H20F,H20G)
4.b Aromatic/amide H refined with riding coordinates:
 C103(H103), C104(H104), C106(H106), C107(H107), C111(H111), C112(H112),
 C115(H115), C117(H117), C118(H118), C119(H119), C120(H120), C203(H203),
 C204(H204), C206(H206), C207(H207), C211(H211), C212(H212), C215(H215),
 C217(H217), C218(H218), C219(H219), C220(H220)
4.c Idealised Me refined as rotating group:
 C101(H10A,H10B,H10C), C201(H20A,H20B,H20C)
;
_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
C101 C 0.1414(12) -0.2793(14) 0.26868(12) 0.0405(19) Uani 1 1 d . . . . .
H10A H 0.101748 -0.392010 0.277967 0.061 Uiso 1 1 calc R U . . .
H10B H 0.267964 -0.259146 0.270482 0.061 Uiso 1 1 calc R U . . .
H10C H 0.114266 -0.323818 0.254747 0.061 Uiso 1 1 calc R U . . .
C102 C 0.0491(9) -0.0139(11) 0.29271(10) 0.0237(13) Uani 1 1 d . . . . .
C103 C -0.0379(9) 0.1814(11) 0.29583(10) 0.0258(14) Uani 1 1 d . . . . .
H103 H -0.086826 0.260195 0.284709 0.031 Uiso 1 1 calc R U . . .
C104 C -0.0526(9) 0.2598(12) 0.31518(10) 0.0253(14) Uani 1 1 d . . . . .
H104 H -0.109550 0.395157 0.317224 0.030 Uiso 1 1 calc R U . . .
C105 C 0.0145(9) 0.1447(11) 0.33195(10) 0.0229(13) Uani 1 1 d . . . . .
C106 C 0.1004(9) -0.0496(12) 0.32816(10) 0.0240(14) Uani 1 1 d . . . . .
H106 H 0.147288 -0.130020 0.339288 0.029 Uiso 1 1 calc R U . . .
C107 C 0.1211(8) -0.1323(11) 0.30874(10) 0.0216(13) Uani 1 1 d . . . . .
H107 H 0.182063 -0.264589 0.306578 0.026 Uiso 1 1 calc R U . . .
C108 C -0.0142(8) 0.2266(13) 0.35298(10) 0.0261(15) Uani 1 1 d . . . . .
H10D H -0.043906 0.101602 0.361665 0.031 Uiso 1 1 calc R U . . .
H10E H -0.115711 0.326691 0.352642 0.031 Uiso 1 1 calc R U . . .
C109 C 0.1444(8) 0.3464(11) 0.36258(10) 0.0221(14) Uani 1 1 d . . . . .
H10F H 0.245728 0.246219 0.363427 0.027 Uiso 1 1 calc R U . . .
H10G H 0.176140 0.470960 0.353936 0.027 Uiso 1 1 calc R U . . .
C110 C 0.1039(8) 0.4280(11) 0.38348(10) 0.0212(13) Uani 1 1 d . . . . .
C111 C 0.0264(8) 0.6327(12) 0.38594(11) 0.0246(14) Uani 1 1 d . . . . .
H111 H 0.005119 0.720204 0.374315 0.029 Uiso 1 1 calc R U . . .
C112 C -0.0201(9) 0.7128(12) 0.40438(11) 0.0280(14) Uani 1 1 d . . . . .
H112 H -0.069238 0.853803 0.405819 0.034 Uiso 1 1 calc R U . . .
C113 C 0.0086(8) 0.5761(12) 0.42078(11) 0.0253(13) Uani 1 1 d . . . . .
C114 C 0.0886(8) 0.3707(11) 0.41913(10) 0.0221(13) Uani 1 1 d . . . . .
C115 C 0.1370(8) 0.2993(11) 0.40011(10) 0.0220(13) Uani 1 1 d . . . . .
H115 H 0.192600 0.162147 0.398649 0.026 Uiso 1 1 calc R U . . .
C116 C 0.0180(9) 0.4424(12) 0.45145(11) 0.0274(14) Uani 1 1 d . . . . .
C117 C -0.0031(11) 0.4168(14) 0.47190(12) 0.0362(17) Uani 1 1 d . . . . .
H117 H -0.055313 0.527004 0.479787 0.043 Uiso 1 1 calc R U . . .
C118 C 0.0543(11) 0.2260(14) 0.48032(12) 0.0378(17) Uani 1 1 d . . . . .
H118 H 0.038534 0.201181 0.494304 0.045 Uiso 1 1 calc R U . . .
C119 C 0.1370(9) 0.0641(15) 0.46867(11) 0.0338(17) Uani 1 1 d . . . . .
H119 H 0.180070 -0.064345 0.475046 0.041 Uiso 1 1 calc R U . . .
C120 C 0.1555(9) 0.0914(12) 0.44805(11) 0.0274(14) Uani 1 1 d . . . . .
H120 H 0.208034 -0.018317 0.440129 0.033 Uiso 1 1 calc R U . . .
C121 C 0.0955(8) 0.2827(11) 0.43939(10) 0.0222(13) Uani 1 1 d . . . . .
C201 C 0.5644(11) 0.7847(13) 0.73057(11) 0.0346(17) Uani 1 1 d . . . . .
H20A H 0.561032 0.819817 0.744977 0.052 Uiso 1 1 calc R U . . .
H20B H 0.511049 0.903557 0.722697 0.052 Uiso 1 1 calc R U . . .
H20C H 0.686212 0.765723 0.726667 0.052 Uiso 1 1 calc R U . . .
C202 C 0.4549(9) 0.5177(11) 0.70719(10) 0.0227(13) Uani 1 1 d . . . . .
C203 C 0.3641(9) 0.3218(11) 0.70412(10) 0.0257(14) Uani 1 1 d . . . . .
H203 H 0.319405 0.244831 0.715297 0.031 Uiso 1 1 calc R U . . .
C204 C 0.3399(9) 0.2419(11) 0.68505(10) 0.0245(13) Uani 1 1 d . . . . .
H204 H 0.279976 0.107748 0.683136 0.029 Uiso 1 1 calc R U . . .
C205 C 0.4014(8) 0.3533(11) 0.66827(10) 0.0231(13) Uani 1 1 d . . . . .
C206 C 0.4923(8) 0.5465(12) 0.67141(10) 0.0223(13) Uani 1 1 d . . . . .
H206 H 0.535302 0.622462 0.660087 0.027 Uiso 1 1 calc R U . . .
C207 C 0.5229(9) 0.6332(11) 0.69080(9) 0.0226(13) Uani 1 1 d . . . . .
H207 H 0.586797 0.764411 0.692772 0.027 Uiso 1 1 calc R U . . .
C208 C 0.3643(8) 0.2685(12) 0.64723(10) 0.0249(14) Uani 1 1 d . . . . .
H20D H 0.330129 0.392194 0.638390 0.030 Uiso 1 1 calc R U . . .
H20E H 0.263660 0.167269 0.647582 0.030 Uiso 1 1 calc R U . . .
C209 C 0.5195(8) 0.1503(12) 0.63800(10) 0.0238(14) Uani 1 1 d . . . . .
H20F H 0.619929 0.251649 0.637378 0.029 Uiso 1 1 calc R U . . .
H20G H 0.554735 0.026954 0.646821 0.029 Uiso 1 1 calc R U . . .
C210 C 0.4766(7) 0.0661(11) 0.61716(10) 0.0207(13) Uani 1 1 d . . . . .
C211 C 0.3996(9) -0.1381(12) 0.61462(10) 0.0249(14) Uani 1 1 d . . . . .
H211 H 0.382864 -0.225721 0.626215 0.030 Uiso 1 1 calc R U . . .
C212 C 0.3459(9) -0.2198(11) 0.59568(10) 0.0259(14) Uani 1 1 d . . . . .
H212 H 0.291282 -0.358012 0.594216 0.031 Uiso 1 1 calc R U . . .
C213 C 0.3767(8) -0.0890(12) 0.57947(10) 0.0247(13) Uani 1 1 d . . . . .
C214 C 0.4535(8) 0.1195(11) 0.58122(10) 0.0228(13) Uani 1 1 d . . . . .
C215 C 0.5034(8) 0.1957(11) 0.60016(10) 0.0234(13) Uani 1 1 d . . . . .
H215 H 0.555547 0.335367 0.601614 0.028 Uiso 1 1 calc R U . . .
C216 C 0.3850(9) 0.0401(13) 0.54879(11) 0.0283(14) Uani 1 1 d . . . . .
C217 C 0.3672(10) 0.0536(16) 0.52815(11) 0.0386(18) Uani 1 1 d . . . . .
H217 H 0.316331 -0.059663 0.520194 0.046 Uiso 1 1 calc R U . . .
C218 C 0.4297(12) 0.2472(18) 0.51965(12) 0.047(2) Uani 1 1 d . . . . .
H218 H 0.419839 0.265685 0.505429 0.056 Uiso 1 1 calc R U . . .
C219 C 0.5058(12) 0.4141(18) 0.53129(13) 0.049(2) Uani 1 1 d . . . . .
H219 H 0.548076 0.541721 0.524949 0.058 Uiso 1 1 calc R U . . .
C220 C 0.5197(9) 0.3922(13) 0.55252(11) 0.0303(15) Uani 1 1 d . . . . .
H220 H 0.568561 0.504980 0.560705 0.036 Uiso 1 1 calc R U . . .
C221 C 0.4603(8) 0.2027(11) 0.56092(10) 0.0216(13) Uani 1 1 d . . . . .
O101 O 0.0540(7) -0.0791(9) 0.27283(7) 0.0295(11) Uani 1 1 d . . . . .
O102 O -0.0346(6) 0.6211(8) 0.44035(7) 0.0291(11) Uani 1 1 d . . . . .
O201 O 0.4709(7) 0.5906(9) 0.72678(7) 0.0294(11) Uani 1 1 d . . . . .
O202 O 0.3317(6) -0.1384(8) 0.55972(7) 0.0281(11) Uani 1 1 d . . . . .


_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
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C101 O101 1.429(9) . ?
C102 C103 1.390(10) . ?
C102 C107 1.390(9) . ?
C102 O101 1.379(8) . ?
C103 H103 0.9500 . ?
C103 C104 1.378(10) . ?
C104 H104 0.9500 . ?
C104 C105 1.403(10) . ?
C105 C106 1.389(10) . ?
C105 C108 1.503(9) . ?
C106 H106 0.9500 . ?
C106 C107 1.396(9) . ?
C107 H107 0.9500 . ?
C108 H10D 0.9900 . ?
C108 H10E 0.9900 . ?
C108 C109 1.541(9) . ?
C109 H10F 0.9900 . ?
C109 H10G 0.9900 . ?
C109 C110 1.513(9) . ?
C110 C111 1.402(10) . ?
C110 C115 1.375(9) . ?
C111 H111 0.9500 . ?
C111 C112 1.373(10) . ?
C112 H112 0.9500 . ?
C112 C113 1.386(10) . ?
C113 C114 1.408(10) . ?
C113 O102 1.375(8) . ?
C114 C115 1.394(9) . ?
C114 C121 1.448(9) . ?
C115 H115 0.9500 . ?
C116 C117 1.378(10) . ?
C116 C121 1.406(9) . ?
C116 O102 1.376(9) . ?
C117 H117 0.9500 . ?
C117 C118 1.366(12) . ?
C118 H118 0.9500 . ?
C118 C119 1.418(11) . ?
C119 H119 0.9500 . ?
C119 C120 1.388(10) . ?
C120 H120 0.9500 . ?
C120 C121 1.381(10) . ?
C201 H20A 0.9800 . ?
C201 H20B 0.9800 . ?
C201 H20C 0.9800 . ?
C201 O201 1.410(9) . ?
C202 C203 1.402(10) . ?
C202 C207 1.409(9) . ?
C202 O201 1.375(8) . ?
C203 H203 0.9500 . ?
C203 C204 1.364(10) . ?
C204 H204 0.9500 . ?
C204 C205 1.398(9) . ?
C205 C206 1.388(10) . ?
C205 C208 1.508(9) . ?
C206 H206 0.9500 . ?
C206 C207 1.405(9) . ?
C207 H207 0.9500 . ?
C208 H20D 0.9900 . ?
C208 H20E 0.9900 . ?
C208 C209 1.533(9) . ?
C209 H20F 0.9900 . ?
C209 H20G 0.9900 . ?
C209 C210 1.503(9) . ?
C210 C211 1.394(10) . ?
C210 C215 1.399(10) . ?
C211 H211 0.9500 . ?
C211 C212 1.403(9) . ?
C212 H212 0.9500 . ?
C212 C213 1.367(10) . ?
C213 C214 1.413(10) . ?
C213 O202 1.378(8) . ?
C214 C215 1.384(9) . ?
C214 C221 1.442(10) . ?
C215 H215 0.9500 . ?
C216 C217 1.374(10) . ?
C216 C221 1.397(10) . ?
C216 O202 1.381(9) . ?
C217 H217 0.9500 . ?
C217 C218 1.405(13) . ?
C218 H218 0.9500 . ?
C218 C219 1.401(14) . ?
C219 H219 0.9500 . ?
C219 C220 1.415(11) . ?
C220 H220 0.9500 . ?
C220 C221 1.373(10) . ?

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
H10A C101 H10B 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O101 C101 H10A 109.5 . . ?
O101 C101 H10B 109.5 . . ?
O101 C101 H10C 109.5 . . ?
C107 C102 C103 121.3(6) . . ?
O101 C102 C103 114.8(6) . . ?
O101 C102 C107 123.9(6) . . ?
C102 C103 H103 120.3 . . ?
C104 C103 C102 119.4(7) . . ?
C104 C103 H103 120.3 . . ?
C103 C104 H104 119.2 . . ?
C103 C104 C105 121.6(7) . . ?
C105 C104 H104 119.2 . . ?
C104 C105 C108 120.4(6) . . ?
C106 C105 C104 117.0(6) . . ?
C106 C105 C108 122.5(6) . . ?
C105 C106 H106 118.5 . . ?
C105 C106 C107 123.0(6) . . ?
C107 C106 H106 118.5 . . ?
C102 C107 C106 117.5(6) . . ?
C102 C107 H107 121.2 . . ?
C106 C107 H107 121.2 . . ?
C105 C108 H10D 108.7 . . ?
C105 C108 H10E 108.7 . . ?
C105 C108 C109 114.2(5) . . ?
H10D C108 H10E 107.6 . . ?
C109 C108 H10D 108.7 . . ?
C109 C108 H10E 108.7 . . ?
C108 C109 H10F 109.4 . . ?
C108 C109 H10G 109.4 . . ?
H10F C109 H10G 108.0 . . ?
C110 C109 C108 111.0(5) . . ?
C110 C109 H10F 109.4 . . ?
C110 C109 H10G 109.4 . . ?
C111 C110 C109 120.1(6) . . ?
C115 C110 C109 120.4(6) . . ?
C115 C110 C111 119.5(6) . . ?
C110 C111 H111 118.5 . . ?
C112 C111 C110 123.1(7) . . ?
C112 C111 H111 118.5 . . ?
C111 C112 H112 121.9 . . ?
C111 C112 C113 116.2(7) . . ?
C113 C112 H112 121.9 . . ?
C112 C113 C114 122.8(6) . . ?
O102 C113 C112 125.5(6) . . ?
O102 C113 C114 111.7(6) . . ?
C113 C114 C121 105.5(6) . . ?
C115 C114 C113 118.6(6) . . ?
C115 C114 C121 135.9(6) . . ?
C110 C115 C114 119.8(6) . . ?
C110 C115 H115 120.1 . . ?
C114 C115 H115 120.1 . . ?
C117 C116 C121 122.8(7) . . ?
O102 C116 C117 125.2(7) . . ?
O102 C116 C121 112.0(6) . . ?
C116 C117 H117 121.5 . . ?
C118 C117 C116 117.1(7) . . ?
C118 C117 H117 121.5 . . ?
C117 C118 H118 119.3 . . ?
C117 C118 C119 121.5(7) . . ?
C119 C118 H118 119.3 . . ?
C118 C119 H119 119.7 . . ?
C120 C119 C118 120.7(8) . . ?
C120 C119 H119 119.7 . . ?
C119 C120 H120 121.0 . . ?
C121 C120 C119 118.1(7) . . ?
C121 C120 H120 121.0 . . ?
C116 C121 C114 105.1(6) . . ?
C120 C121 C114 135.0(6) . . ?
C120 C121 C116 119.9(7) . . ?
H20A C201 H20B 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
O201 C201 H20A 109.5 . . ?
O201 C201 H20B 109.5 . . ?
O201 C201 H20C 109.5 . . ?
C203 C202 C207 120.8(6) . . ?
O201 C202 C203 116.6(6) . . ?
O201 C202 C207 122.6(6) . . ?
C202 C203 H203 120.1 . . ?
C204 C203 C202 119.9(6) . . ?
C204 C203 H203 120.1 . . ?
C203 C204 H204 119.3 . . ?
C203 C204 C205 121.4(7) . . ?
C205 C204 H204 119.3 . . ?
C204 C205 C208 120.5(6) . . ?
C206 C205 C204 118.5(6) . . ?
C206 C205 C208 121.0(6) . . ?
C205 C206 H206 118.9 . . ?
C205 C206 C207 122.1(6) . . ?
C207 C206 H206 118.9 . . ?
C202 C207 H207 121.3 . . ?
C206 C207 C202 117.3(6) . . ?
C206 C207 H207 121.3 . . ?
C205 C208 H20D 108.8 . . ?
C205 C208 H20E 108.8 . . ?
C205 C208 C209 113.8(5) . . ?
H20D C208 H20E 107.7 . . ?
C209 C208 H20D 108.8 . . ?
C209 C208 H20E 108.8 . . ?
C208 C209 H20F 109.2 . . ?
C208 C209 H20G 109.2 . . ?
H20F C209 H20G 107.9 . . ?
C210 C209 C208 112.2(5) . . ?
C210 C209 H20F 109.2 . . ?
C210 C209 H20G 109.2 . . ?
C211 C210 C209 120.1(6) . . ?
C211 C210 C215 119.0(6) . . ?
C215 C210 C209 120.7(6) . . ?
C210 C211 H211 118.6 . . ?
C210 C211 C212 122.9(7) . . ?
C212 C211 H211 118.6 . . ?
C211 C212 H212 121.9 . . ?
C213 C212 C211 116.1(7) . . ?
C213 C212 H212 121.9 . . ?
C212 C213 C214 123.2(6) . . ?
C212 C213 O202 125.0(7) . . ?
O202 C213 C214 111.7(6) . . ?
C213 C214 C221 105.6(6) . . ?
C215 C214 C213 119.0(6) . . ?
C215 C214 C221 135.3(7) . . ?
C210 C215 H215 120.2 . . ?
C214 C215 C210 119.7(6) . . ?
C214 C215 H215 120.2 . . ?
C217 C216 C221 123.9(8) . . ?
C217 C216 O202 123.2(7) . . ?
O202 C216 C221 112.9(6) . . ?
C216 C217 H217 122.4 . . ?
C216 C217 C218 115.2(8) . . ?
C218 C217 H217 122.4 . . ?
C217 C218 H218 118.7 . . ?
C219 C218 C217 122.6(8) . . ?
C219 C218 H218 118.7 . . ?
C218 C219 H219 120.1 . . ?
C218 C219 C220 119.8(9) . . ?
C220 C219 H219 120.1 . . ?
C219 C220 H220 121.1 . . ?
C221 C220 C219 117.8(8) . . ?
C221 C220 H220 121.1 . . ?
C216 C221 C214 105.0(6) . . ?
C220 C221 C214 134.4(7) . . ?
C220 C221 C216 120.6(7) . . ?
C102 O101 C101 117.3(6) . . ?
C113 O102 C116 105.6(5) . . ?
C202 O201 C201 118.4(5) . . ?
C213 O202 C216 104.7(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
C102 C103 C104 C105 -1.6(10) . . . . ?
C103 C102 C107 C106 1.0(10) . . . . ?
C103 C102 O101 C101 -179.8(6) . . . . ?
C103 C104 C105 C106 1.5(10) . . . . ?
C103 C104 C105 C108 -175.8(6) . . . . ?
C104 C105 C106 C107 -0.2(10) . . . . ?
C104 C105 C108 C109 -100.7(8) . . . . ?
C105 C106 C107 C102 -1.0(10) . . . . ?
C105 C108 C109 C110 178.7(6) . . . . ?
C106 C105 C108 C109 82.1(8) . . . . ?
C107 C102 C103 C104 0.3(10) . . . . ?
C107 C102 O101 C101 -1.1(10) . . . . ?
C108 C105 C106 C107 177.1(6) . . . . ?
C108 C109 C110 C111 -87.6(7) . . . . ?
C108 C109 C110 C115 90.1(7) . . . . ?
C109 C110 C111 C112 177.3(6) . . . . ?
C109 C110 C115 C114 -175.8(6) . . . . ?
C110 C111 C112 C113 -2.0(10) . . . . ?
C111 C110 C115 C114 1.9(9) . . . . ?
C111 C112 C113 C114 3.1(10) . . . . ?
C111 C112 C113 O102 -177.4(6) . . . . ?
C112 C113 C114 C115 -1.7(10) . . . . ?
C112 C113 C114 C121 179.4(6) . . . . ?
C112 C113 O102 C116 -179.7(7) . . . . ?
C113 C114 C115 C110 -0.8(9) . . . . ?
C113 C114 C121 C116 0.3(7) . . . . ?
C113 C114 C121 C120 179.5(7) . . . . ?
C114 C113 O102 C116 -0.1(7) . . . . ?
C115 C110 C111 C112 -0.4(9) . . . . ?
C115 C114 C121 C116 -178.2(7) . . . . ?
C115 C114 C121 C120 1.0(13) . . . . ?
C116 C117 C118 C119 1.9(12) . . . . ?
C117 C116 C121 C114 178.7(7) . . . . ?
C117 C116 C121 C120 -0.6(10) . . . . ?
C117 C116 O102 C113 -178.8(7) . . . . ?
C117 C118 C119 C120 -2.7(12) . . . . ?
C118 C119 C120 C121 1.7(11) . . . . ?
C119 C120 C121 C114 -179.2(7) . . . . ?
C119 C120 C121 C116 -0.1(10) . . . . ?
C121 C114 C115 C110 177.6(7) . . . . ?
C121 C116 C117 C118 -0.3(11) . . . . ?
C121 C116 O102 C113 0.3(7) . . . . ?
C202 C203 C204 C205 -1.1(10) . . . . ?
C203 C202 C207 C206 1.4(10) . . . . ?
C203 C202 O201 C201 178.7(6) . . . . ?
C203 C204 C205 C206 1.6(10) . . . . ?
C203 C204 C205 C208 -176.5(6) . . . . ?
C204 C205 C206 C207 -0.5(10) . . . . ?
C204 C205 C208 C209 -101.8(7) . . . . ?
C205 C206 C207 C202 -0.9(10) . . . . ?
C205 C208 C209 C210 179.3(6) . . . . ?
C206 C205 C208 C209 80.2(8) . . . . ?
C207 C202 C203 C204 -0.4(10) . . . . ?
C207 C202 O201 C201 -2.3(10) . . . . ?
C208 C205 C206 C207 177.6(6) . . . . ?
C208 C209 C210 C211 -86.9(8) . . . . ?
C208 C209 C210 C215 89.3(7) . . . . ?
C209 C210 C211 C212 175.7(6) . . . . ?
C209 C210 C215 C214 -176.3(6) . . . . ?
C210 C211 C212 C213 1.4(10) . . . . ?
C211 C210 C215 C214 0.0(9) . . . . ?
C211 C212 C213 C214 -1.7(10) . . . . ?
C211 C212 C213 O202 -179.1(6) . . . . ?
C212 C213 C214 C215 1.1(10) . . . . ?
C212 C213 C214 C221 -179.2(6) . . . . ?
C212 C213 O202 C216 179.1(7) . . . . ?
C213 C214 C215 C210 -0.2(9) . . . . ?
C213 C214 C221 C216 1.0(7) . . . . ?
C213 C214 C221 C220 -179.6(7) . . . . ?
C214 C213 O202 C216 1.4(7) . . . . ?
C215 C210 C211 C212 -0.6(9) . . . . ?
C215 C214 C221 C216 -179.5(7) . . . . ?
C215 C214 C221 C220 -0.1(13) . . . . ?
C216 C217 C218 C219 0.4(12) . . . . ?
C217 C216 C221 C214 -179.4(7) . . . . ?
C217 C216 C221 C220 1.1(10) . . . . ?
C217 C216 O202 C213 178.5(7) . . . . ?
C217 C218 C219 C220 -0.9(14) . . . . ?
C218 C219 C220 C221 1.4(12) . . . . ?
C219 C220 C221 C214 179.1(7) . . . . ?
C219 C220 C221 C216 -1.5(10) . . . . ?
C221 C214 C215 C210 -179.7(7) . . . . ?
C221 C216 C217 C218 -0.5(11) . . . . ?
C221 C216 O202 C213 -0.8(7) . . . . ?
O101 C102 C103 C104 179.1(6) . . . . ?
O101 C102 C107 C106 -177.7(6) . . . . ?
O102 C113 C114 C115 178.7(6) . . . . ?
O102 C113 C114 C121 -0.2(7) . . . . ?
O102 C116 C117 C118 178.7(7) . . . . ?
O102 C116 C121 C114 -0.4(7) . . . . ?
O102 C116 C121 C120 -179.7(6) . . . . ?
O201 C202 C203 C204 178.6(6) . . . . ?
O201 C202 C207 C206 -177.6(6) . . . . ?
O202 C213 C214 C215 178.8(6) . . . . ?
O202 C213 C214 C221 -1.5(7) . . . . ?
O202 C216 C217 C218 -179.7(7) . . . . ?
O202 C216 C221 C214 -0.1(7) . . . . ?
O202 C216 C221 C220 -179.6(6) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-479
_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 1.600
_oxdiff_exptl_absorpt_empirical_full_min 0.581
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.693(4)
2 0.307(4)

####################################################################### 
# 
# 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_2022acc0022_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 2204910'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2022-09-02 deposited with the CCDC.	2023-06-21 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535)
;
_shelx_SHELXL_version_number     2016/6
loop_
_audit_author_email
'g.mcglacken@ucc.ie '
light@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H23 N O4'
_chemical_formula_sum            'C23 H23 N O4'
_chemical_formula_weight         377.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H12N2O3
_chemical_oxdiff_usercomment     RAK-439
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'
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                   5.40640(10)
_cell_length_b                   9.64370(10)
_cell_length_c                   36.2282(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1888.86(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12143
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1450
_cell_measurement_theta_min      4.7230
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.917
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0437
0 0 -1 0.0097
1 -5 3 0.0418
-1 5 -3 0.0418
3 0 -2 0.0573
-3 0 2 0.0573
2 5 4 0.0416
-2 -5 -5 0.0551
0 1 5 0.0399
-1 0 5 0.0437
-1 -2 5 0.0461

_exptl_crystal_recrystallization_method 
'The material was recrystallised from --- by slow evaporation'
_exptl_crystal_size_max          0.12
_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
0.0000 -0.0000 0.9996 0.0055 -0.0396 0.0145
-0.0000 0.0000 -0.9996 -0.0055 0.0396 -0.0145
1.0039 -4.9966 3.0240 0.1557 -0.3910 -0.7473
-1.0039 4.9966 -3.0240 -0.1557 0.3910 0.7473
2.9964 0.0066 -1.9862 0.8224 0.1288 -0.2075
-2.9964 -0.0066 1.9862 -0.8224 -0.1288 0.2075
1.9928 5.0030 3.9860 0.7165 0.1636 0.6703
-1.9928 -5.0030 -4.9856 -0.7220 -0.1240 -0.6849
-0.0008 0.9996 4.9937 0.0554 -0.1401 0.2188
-0.9986 -0.0023 4.9936 -0.2502 -0.2145 0.1320
-0.9966 -2.0018 5.0020 -0.3057 -0.3300 -0.1605

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            18320
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.382
_diffrn_reflns_theta_min         4.745
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  80.00   0.50    1.00    --   45.09-111.00 -43.00  156
  2  ω   -171.00 -90.00   0.50    2.00    --  -97.00 -31.00 164.00  162
  3  ω    -92.00 -27.00   0.50    2.00    --  -97.00 111.00  50.00  130
  4  ω     40.00  92.00   0.50    2.00    --  109.75-111.00 -43.00  104
  5  ω    100.00 175.00   0.50    2.00    --  109.75  97.00 151.00  150
  6  ω    -23.00  30.00   0.50    1.00    --  -45.09  38.00   0.00  106
  7  ω    -23.00  30.00   0.50    1.00    --  -45.09  38.00  60.00  106
  8  ω    -31.00   4.00   0.50    1.00    --   45.09 -31.00 164.00   70
  9  ω    -30.00  15.00   0.50    1.00    --   45.09 -38.00  60.00   90
 10  ω    -79.00 -23.00   0.50    2.00    --  -97.00  77.00 150.00  112
 11  ω    -55.00 -23.00   0.50    2.00    --  -97.00  61.00  90.00   64
 12  ω   -170.00-106.00   0.50    2.00    --  -97.00 -95.00 -90.00  128
 13  ω    -55.00 -23.00   0.50    2.00    --  -97.00  61.00  60.00   64
 14  ω    -55.00 -23.00   0.50    2.00    --  -97.00  61.00 -30.00   64
 15  ω    -55.00 -23.00   0.50    2.00    --  -97.00  61.00 150.00   64
 16  ω    104.00 132.00   0.50    2.00    --  109.75  15.00 150.00   56
 17  ω    104.00 132.00   0.50    2.00    --  109.75  15.00 120.00   56
 18  ω     37.00  71.00   0.50    2.00    --  109.75 -77.00  30.00   68
 19  ω    104.00 132.00   0.50    2.00    --  109.75  15.00  90.00   56
 20  ω    104.00 132.00   0.50    2.00    --  109.75  15.00 -90.00   56
 21  ω     39.00 100.00   0.50    2.00    --  109.75-125.00 150.00  122
 22  ω    104.00 132.00   0.50    2.00    --  109.75  15.00 -60.00   56
 23  ω     37.00  71.00   0.50    2.00    --  109.75 -77.00-120.00   68
 24  ω     40.00 121.00   0.50    1.00    --   45.09  31.00 -35.00  162
 25  ω    -30.00  15.00   0.50    1.00    --   45.09 -38.00-150.00   90
 26  ω     39.00 120.00   0.50    1.00    --   45.09  38.00-120.00  162
 27  ω     39.00 120.00   0.50    1.00    --   45.09  38.00  30.00  162
 28  ω     39.00 120.00   0.50    1.00    --   45.09  38.00  90.00  162
 29  ω   -140.00-104.00   0.50    2.00    --  -97.00 -15.00 -30.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.2780730000
_diffrn_orient_matrix_UB_12      0.0280521000
_diffrn_orient_matrix_UB_13      0.0055186000
_diffrn_orient_matrix_UB_21      0.0166241000
_diffrn_orient_matrix_UB_22      0.0576240000
_diffrn_orient_matrix_UB_23      -0.0395939000
_diffrn_orient_matrix_UB_31      -0.0599502000
_diffrn_orient_matrix_UB_32      0.1463000000
_diffrn_orient_matrix_UB_33      0.0145194000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.666
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3609
_reflns_number_total             3778
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1393 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.16(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0293
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+0.3378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0751
_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 Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C13(H13), C14(H14), C19(H19), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C23(H23A,H23B,H23C)
;
_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
C1 C -0.2819(3) -0.17584(17) 0.72724(5) 0.0179(4) Uani 1 1 d . . . . .
C2 C -0.3719(4) -0.1051(2) 0.76226(5) 0.0249(4) Uani 1 1 d . . . . .
H2A H -0.230756 -0.064451 0.775329 0.037 Uiso 1 1 calc R U . . .
H2B H -0.453138 -0.173444 0.778196 0.037 Uiso 1 1 calc R U . . .
H2C H -0.489901 -0.031841 0.755826 0.037 Uiso 1 1 calc R U . . .
C3 C -0.1099(4) -0.29541(19) 0.73676(5) 0.0231(4) Uani 1 1 d . . . . .
H3A H -0.052353 -0.339682 0.713977 0.035 Uiso 1 1 calc R U . . .
H3B H -0.198998 -0.363448 0.751824 0.035 Uiso 1 1 calc R U . . .
H3C H 0.032509 -0.260137 0.750619 0.035 Uiso 1 1 calc R U . . .
C4 C -0.4919(4) -0.22484(19) 0.70262(5) 0.0225(4) Uani 1 1 d . . . . .
H4A H -0.602747 -0.146926 0.697329 0.034 Uiso 1 1 calc R U . . .
H4B H -0.584436 -0.298331 0.715204 0.034 Uiso 1 1 calc R U . . .
H4C H -0.424008 -0.260871 0.679445 0.034 Uiso 1 1 calc R U . . .
C5 C -0.2046(3) 0.03782(18) 0.69190(5) 0.0171(4) Uani 1 1 d . . . . .
C6 C -0.0165(3) 0.10022(18) 0.66596(5) 0.0189(4) Uani 1 1 d . . . . .
H6A H -0.011131 0.044140 0.643084 0.023 Uiso 1 1 calc R U . . .
H6B H 0.148818 0.095254 0.677622 0.023 Uiso 1 1 calc R U . . .
C7 C -0.0711(4) 0.25113(17) 0.65577(5) 0.0187(4) Uani 1 1 d . . . . .
H7A H -0.250200 0.261902 0.650810 0.022 Uiso 1 1 calc R U . . .
H7B H -0.027721 0.311977 0.676799 0.022 Uiso 1 1 calc R U . . .
C8 C 0.0741(4) 0.29502(17) 0.62208(5) 0.0167(3) Uani 1 1 d . . . . .
C9 C 0.2722(3) 0.38431(16) 0.62385(5) 0.0167(4) Uani 1 1 d . . . . .
H9 H 0.322923 0.420532 0.647029 0.020 Uiso 1 1 calc R U . . .
C10 C 0.4012(3) 0.42270(16) 0.59133(4) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.3261(3) 0.36838(17) 0.55636(5) 0.0168(4) Uani 1 1 d . . . . .
C12 C 0.1231(4) 0.27635(17) 0.55526(5) 0.0189(4) Uani 1 1 d . . . . .
H12 H 0.070152 0.238578 0.532366 0.023 Uiso 1 1 calc R U . . .
C13 C 0.0023(3) 0.24147(18) 0.58722(5) 0.0188(4) Uani 1 1 d . . . . .
H13 H -0.133880 0.179409 0.585979 0.023 Uiso 1 1 calc R U . . .
C14 C 0.6248(4) 0.48899(18) 0.52375(5) 0.0183(4) Uani 1 1 d . . . . .
H14 H 0.702644 0.512027 0.501047 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7149(3) 0.54946(17) 0.55655(5) 0.0165(4) Uani 1 1 d . . . . .
C16 C 0.6017(3) 0.51491(17) 0.58942(4) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.9007(3) 0.65916(17) 0.60430(4) 0.0159(3) Uani 1 1 d . . . . .
C18 C 0.9124(3) 0.64428(17) 0.56573(4) 0.0159(3) Uani 1 1 d . . . . .
C19 C 1.0935(3) 0.71519(17) 0.54604(5) 0.0172(3) Uani 1 1 d . . . . .
H19 H 1.104970 0.706641 0.519967 0.021 Uiso 1 1 calc R U . . .
C20 C 1.2574(3) 0.79886(17) 0.56550(5) 0.0164(3) Uani 1 1 d . . . . .
C21 C 1.2418(3) 0.81261(17) 0.60401(5) 0.0179(4) Uani 1 1 d . . . . .
H21 H 1.355912 0.870535 0.616650 0.021 Uiso 1 1 calc R U . . .
C22 C 1.0599(3) 0.74187(17) 0.62392(5) 0.0183(4) Uani 1 1 d . . . . .
H22 H 1.047075 0.750668 0.649964 0.022 Uiso 1 1 calc R U . . .
C23 C 1.5846(4) 0.96676(18) 0.56127(5) 0.0217(4) Uani 1 1 d . . . . .
H23A H 1.685737 1.012501 0.542414 0.033 Uiso 1 1 calc R U . . .
H23B H 1.692707 0.923030 0.579602 0.033 Uiso 1 1 calc R U . . .
H23C H 1.479190 1.035617 0.573452 0.033 Uiso 1 1 calc R U . . .
N1 N 0.4370(3) 0.40182(15) 0.52331(4) 0.0187(3) Uani 1 1 d . . . . .
O1 O -0.4054(3) 0.08663(13) 0.69834(4) 0.0233(3) Uani 1 1 d . . . . .
O2 O -0.1184(2) -0.08229(12) 0.70565(3) 0.0181(3) Uani 1 1 d . . . . .
O3 O 0.7093(2) 0.57976(12) 0.61921(3) 0.0166(3) Uani 1 1 d . . . . .
O4 O 1.4336(2) 0.86371(13) 0.54434(3) 0.0205(3) Uani 1 1 d . . . . .


_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
C1 C2 1.520(2) . ?
C1 C3 1.521(3) . ?
C1 C4 1.519(3) . ?
C1 O2 1.486(2) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.509(2) . ?
C5 O1 1.206(2) . ?
C5 O2 1.344(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.530(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(2) . ?
C8 C9 1.376(3) . ?
C8 C13 1.418(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.418(2) . ?
C10 C11 1.430(2) . ?
C10 C16 1.404(3) . ?
C11 C12 1.412(3) . ?
C11 N1 1.378(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.371(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C14 C15 1.411(2) . ?
C14 N1 1.318(2) . ?
C15 C16 1.380(2) . ?
C15 C18 1.444(3) . ?
C16 O3 1.376(2) . ?
C17 C18 1.406(2) . ?
C17 C22 1.372(2) . ?
C17 O3 1.396(2) . ?
C18 C19 1.391(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 C21 1.404(2) . ?
C20 O4 1.374(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.397(3) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 O4 1.425(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
C2 C1 C3 110.28(15) . . ?
C4 C1 C2 112.97(16) . . ?
C4 C1 C3 110.75(15) . . ?
O2 C1 C2 110.94(14) . . ?
O2 C1 C3 102.47(14) . . ?
O2 C1 C4 108.94(13) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O1 C5 C6 124.83(16) . . ?
O1 C5 O2 125.21(17) . . ?
O2 C5 C6 109.93(15) . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.54(15) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.15(15) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C9 C8 C7 122.82(15) . . ?
C9 C8 C13 118.84(16) . . ?
C13 C8 C7 118.33(16) . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.50(16) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C11 120.04(16) . . ?
C16 C10 C9 125.89(15) . . ?
C16 C10 C11 114.06(15) . . ?
C12 C11 C10 118.44(15) . . ?
N1 C11 C10 124.10(16) . . ?
N1 C11 C12 117.45(15) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 C11 120.02(15) . . ?
C13 C12 H12 120.0 . . ?
C8 C13 H13 118.9 . . ?
C12 C13 C8 122.16(17) . . ?
C12 C13 H13 118.9 . . ?
C15 C14 H14 118.7 . . ?
N1 C14 H14 118.7 . . ?
N1 C14 C15 122.66(16) . . ?
C14 C15 C18 135.31(16) . . ?
C16 C15 C14 118.30(16) . . ?
C16 C15 C18 106.38(14) . . ?
C15 C16 C10 122.56(15) . . ?
O3 C16 C10 125.12(14) . . ?
O3 C16 C15 112.32(15) . . ?
C22 C17 C18 123.09(16) . . ?
C22 C17 O3 125.69(15) . . ?
O3 C17 C18 111.22(15) . . ?
C17 C18 C15 105.09(15) . . ?
C19 C18 C15 135.50(15) . . ?
C19 C18 C17 119.41(16) . . ?
C18 C19 H19 120.9 . . ?
C20 C19 C18 118.27(15) . . ?
C20 C19 H19 120.9 . . ?
C19 C20 C21 121.37(16) . . ?
O4 C20 C19 115.03(14) . . ?
O4 C20 C21 123.59(16) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.60(16) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 117.25(15) . . ?
C17 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O4 C23 H23A 109.5 . . ?
O4 C23 H23B 109.5 . . ?
O4 C23 H23C 109.5 . . ?
C14 N1 C11 118.31(15) . . ?
C5 O2 C1 120.80(14) . . ?
C16 O3 C17 105.00(12) . . ?
C20 O4 C23 118.33(13) . . ?

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
C2 C1 O2 C5 -62.4(2) . . . . ?
C3 C1 O2 C5 179.87(14) . . . . ?
C4 C1 O2 C5 62.51(19) . . . . ?
C5 C6 C7 C8 -163.53(15) . . . . ?
C6 C5 O2 C1 -170.33(14) . . . . ?
C6 C7 C8 C9 -107.70(19) . . . . ?
C6 C7 C8 C13 72.3(2) . . . . ?
C7 C8 C9 C10 -179.64(16) . . . . ?
C7 C8 C13 C12 179.69(16) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C8 C9 C10 C16 178.50(16) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C9 C10 C11 C12 -0.2(2) . . . . ?
C9 C10 C11 N1 178.71(16) . . . . ?
C9 C10 C16 C15 -178.64(17) . . . . ?
C9 C10 C16 O3 1.9(3) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C10 C11 N1 C14 0.2(3) . . . . ?
C10 C16 O3 C17 179.35(16) . . . . ?
C11 C10 C16 C15 0.0(2) . . . . ?
C11 C10 C16 O3 -179.37(15) . . . . ?
C11 C12 C13 C8 0.0(3) . . . . ?
C12 C11 N1 C14 179.15(16) . . . . ?
C13 C8 C9 C10 0.4(2) . . . . ?
C14 C15 C16 C10 -0.2(3) . . . . ?
C14 C15 C16 O3 179.32(15) . . . . ?
C14 C15 C18 C17 -179.1(2) . . . . ?
C14 C15 C18 C19 0.3(4) . . . . ?
C15 C14 N1 C11 -0.3(3) . . . . ?
C15 C16 O3 C17 -0.12(18) . . . . ?
C15 C18 C19 C20 -179.37(18) . . . . ?
C16 C10 C11 C12 -178.98(15) . . . . ?
C16 C10 C11 N1 -0.1(2) . . . . ?
C16 C15 C18 C17 -0.05(18) . . . . ?
C16 C15 C18 C19 179.35(19) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C18 C15 C16 C10 -179.38(15) . . . . ?
C18 C15 C16 O3 0.11(19) . . . . ?
C18 C17 C22 C21 -0.5(3) . . . . ?
C18 C17 O3 C16 0.09(18) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 O4 178.93(15) . . . . ?
C19 C20 C21 C22 0.1(3) . . . . ?
C19 C20 O4 C23 170.84(15) . . . . ?
C20 C21 C22 C17 0.3(3) . . . . ?
C21 C20 O4 C23 -10.1(2) . . . . ?
C22 C17 C18 C15 179.94(16) . . . . ?
C22 C17 C18 C19 0.4(3) . . . . ?
C22 C17 O3 C16 -179.87(17) . . . . ?
N1 C11 C12 C13 -178.73(16) . . . . ?
N1 C14 C15 C16 0.3(3) . . . . ?
N1 C14 C15 C18 179.25(18) . . . . ?
O1 C5 C6 C7 15.2(3) . . . . ?
O1 C5 O2 C1 7.5(3) . . . . ?
O2 C5 C6 C7 -166.97(14) . . . . ?
O3 C17 C18 C15 -0.03(19) . . . . ?
O3 C17 C18 C19 -179.54(15) . . . . ?
O3 C17 C22 C21 179.42(15) . . . . ?
O4 C20 C21 C22 -178.98(15) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id RAK-439
_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 1.814
_oxdiff_exptl_absorpt_empirical_full_min 0.604
