# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kjw-2024-220
_database_code_depnum_ccdc_archive 'CCDC 2374388'
loop_
_audit_author_name
_audit_author_address
'Nathan D. Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2024-06-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H2 Cl2, C24 H24 F N3 O3'
_chemical_formula_sum            'C25 H26 Cl2 F N3 O3'
_chemical_formula_weight         506.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23.5H26Cl2N4.5O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   9.8105(3)
_cell_length_b                   10.5343(4)
_cell_length_c                   13.5571(6)
_cell_angle_alpha                109.987(4)
_cell_angle_beta                 96.545(3)
_cell_angle_gamma                110.033(3)
_cell_volume                     1193.91(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9156
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.5620
_cell_measurement_theta_min      3.5740
_shelx_estimated_absorpt_T_max   0.896
_shelx_estimated_absorpt_T_min   0.679
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.722
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.116a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 3 6 0.0229
3 -3 -6 0.0129
-3 7 -2 0.0604
5 -2 5 0.0365
4 -7 2 0.0421
-2 -3 -3 0.0667
-5 -1 5 0.0601
6 -2 -5 0.0095

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_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
-2.9385 3.0981 5.9656 -0.6806 0.3231 -0.6576
2.9385 -3.0981 -5.9656 0.6806 -0.3231 0.6576
-3.4442 6.6612 -2.0613 -0.6910 -0.5902 -0.4173
4.7776 -2.3950 4.8192 0.5972 0.5118 -0.6176
3.7855 -6.5555 2.4848 0.7191 0.6144 0.3248
-2.2650 -2.8850 -3.4359 -0.0709 -0.0623 0.9955
-5.1730 -1.2460 5.0859 -0.7505 0.5756 0.3248
5.7310 -1.7306 -4.5605 0.9428 -0.3332 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4533
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.732
_diffrn_reflns_theta_min         3.594
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1506
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -35.84 -57.00-150.00   84
  2  ω    -55.00  33.00   1.00    1.00    --  -35.84  38.00   0.00   88
  3  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00 120.00   88
  4  ω    -55.00  33.00   1.00    1.00    --  -35.84  38.00   0.00   88
  5  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00  90.00   95
  6  ω      8.00  42.00   1.00    1.00    --   35.84  79.00 140.70   34
  7  ω      9.00  42.00   1.00    1.00    --   35.84  77.00 -10.84   33
  8  ω      9.00  42.00   1.00    1.00    --   35.84  77.00-178.25   33
  9  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  30.00   84
 10  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00 -90.00   84
 11  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00 -90.00   84
 12  ω      9.00  42.00   1.00    1.00    --   35.84  78.00 -55.99   33
 13  ω    -31.00  53.00   1.00    1.00    --   35.84 -57.00-120.00   84
 14  ω      9.00  42.00   1.00    1.00    --   35.84  78.00  43.89   33
 15  ω     19.00 103.00   1.00    1.00    --   35.84  57.00  30.00   84
 16  ω      9.00  42.00   1.00    1.00    --   35.84  78.00-131.57   33
 17  ω     41.00 135.00   1.00    8.00    --  108.40 -77.00 -30.00   94
 18  ω     40.00 126.00   1.00    8.00    --  108.40 -45.00 150.00   86
 19  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00  64.60   95
 20  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00 -30.00   92
 21  ω     87.00 178.00   1.00    8.00    --  108.40  30.00-120.00   91
 22  ω    103.00 176.00   1.00    8.00    --  108.40  77.00 150.00   73
 23  ω     91.00 177.00   1.00    8.00    --  108.40  45.00  60.00   86
 24  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00-120.00   92
 25  ω     41.00 137.00   1.00    8.00    --  108.40 -80.00-149.71   96
 26  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00   6.98   95
 27  ω     91.00 177.00   1.00    8.00    --  108.40  45.00 120.00   86
 28  ω     38.00 130.00   1.00    8.00    --  108.40 -30.00  60.00   92
 29  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00  35.94   95
 30  ω     41.00 136.00   1.00    8.00    --  108.40 -79.00 -86.44   95
 31  ω     41.00 137.00   1.00    8.00    --  108.40 -80.00 147.40   96
 32  ω   -103.00 -19.00   1.00    1.00    --  -35.84 -57.00 -90.00   84
 33  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00   0.00   95
 34  ω   -103.00 -19.00   1.00    1.00    --  -35.84 -57.00 -60.00   84
 35  ω    -63.00  32.00   1.00    1.00    --  -35.84  77.00-120.00   95
 36  ω    -53.00  31.00   1.00    1.00    --  -35.84  57.00-180.00   84
 37  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00-150.00   88
 38  ω    -53.00  31.00   1.00    1.00    --  -35.84  57.00  30.00   84
 39  ω   -105.00 -17.00   1.00    1.00    --  -35.84 -38.00  30.00   88
 40  ω     19.00 103.00   1.00    1.00    --   35.84  57.00 120.00   84
 41  ω     10.00  36.00   1.00    1.00    --   35.84  75.00 -90.78   26
 42  ω    -21.00  63.00   1.00    1.00    --   35.84 -77.00 120.00   84
 43  ω      9.00  42.00   1.00    1.00    --   35.84  78.00  99.48   33
 44  ω     87.00 178.00   1.00    8.00    --  108.40  30.00   0.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1295121000
_diffrn_orient_matrix_UB_12      -0.0450851000
_diffrn_orient_matrix_UB_13      -0.0268719000
_diffrn_orient_matrix_UB_21      -0.0121197000
_diffrn_orient_matrix_UB_22      -0.0688876000
_diffrn_orient_matrix_UB_23      0.0839742000
_diffrn_orient_matrix_UB_31      -0.1143307000
_diffrn_orient_matrix_UB_32      -0.1493063000
_diffrn_orient_matrix_UB_33      -0.0890084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4016
_reflns_number_total             4533
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.116a 64-bit (release 22-03-2024))'
_computing_data_reduction        'CrysAlisPro 1.171.43.116a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.582
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.202
_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)+5.1172P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1707
_refine_ls_wR_factor_ref         0.1731
_refine_special_details          
'Twinning was identified using the TWINROTMAT tool in Platon which was resolved by generating and refining against a detwinned HKLF5 reflection file.'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.738(4)
 0.262(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.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C4(H4A,H4B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16), C17(H17),
 C20(H20)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), 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
Cl1 Cl 0.45575(14) 0.68432(14) 1.00347(11) 0.0334(3) Uani 1 1 d . . . . .
Cl2 Cl 0.13927(16) 0.59188(17) 0.90170(11) 0.0440(4) Uani 1 1 d . . . . .
C25 C 0.2690(6) 0.5896(6) 1.0024(4) 0.0314(11) Uani 1 1 d . . . . .
H25A H 0.253440 0.636040 1.074689 0.038 Uiso 1 1 calc R U . . .
H25B H 0.250294 0.485745 0.988670 0.038 Uiso 1 1 calc R U . . .
F1 F 1.0353(3) 0.1836(3) 0.3059(2) 0.0231(6) Uani 1 1 d . . . . .
O1 O 0.7594(4) 0.1974(3) 0.7471(2) 0.0211(7) Uani 1 1 d . . . . .
O2 O 0.7059(3) 0.0505(3) 0.5701(2) 0.0164(6) Uani 1 1 d . . . . .
O3 O 0.5884(3) 0.7236(3) 0.6949(2) 0.0186(6) Uani 1 1 d . . . . .
N1 N 0.5128(4) 0.2674(4) 0.6815(3) 0.0157(7) Uani 1 1 d . . . . .
N2 N 0.7178(4) 0.7641(4) 0.8603(3) 0.0144(7) Uani 1 1 d . . . . .
N3 N 0.8081(4) 0.7216(4) 0.9167(3) 0.0151(7) Uani 1 1 d . . . . .
C1 C 0.6993(4) 0.1597(4) 0.6533(3) 0.0137(8) Uani 1 1 d . . . . .
C2 C 0.6067(4) 0.2303(4) 0.6107(3) 0.0122(8) Uani 1 1 d . . . . .
H2 H 0.539717 0.156973 0.537102 0.015 Uiso 1 1 calc R U . . .
C3 C 0.7111(4) 0.3692(4) 0.5991(3) 0.0123(8) Uani 1 1 d . . . . .
C4 C 0.6139(4) 0.4514(4) 0.5790(3) 0.0126(8) Uani 1 1 d . . . . .
H4A H 0.658086 0.522206 0.546779 0.015 Uiso 1 1 calc R U . . .
H4B H 0.507400 0.385748 0.539546 0.015 Uiso 1 1 calc R U . . .
C5 C 0.6427(4) 0.5229(4) 0.7041(3) 0.0121(8) Uani 1 1 d . . . . .
C6 C 0.7888(4) 0.4962(4) 0.7140(3) 0.0131(8) Uani 1 1 d . . . . .
H6A H 0.879185 0.578852 0.717410 0.016 Uiso 1 1 calc R U . . .
H6B H 0.808517 0.462968 0.772113 0.016 Uiso 1 1 calc R U . . .
C7 C 0.5291(4) 0.4201(4) 0.7415(3) 0.0123(8) Uani 1 1 d . . . . .
H7 H 0.570536 0.449621 0.820623 0.015 Uiso 1 1 calc R U . . .
C8 C 0.3753(5) 0.4215(5) 0.7254(3) 0.0174(9) Uani 1 1 d . . . . .
H8 H 0.360973 0.502632 0.717642 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2588(5) 0.3053(5) 0.7225(4) 0.0186(9) Uani 1 1 d . . . . .
H9 H 0.164362 0.310810 0.724107 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2750(5) 0.1721(5) 0.7168(4) 0.0193(9) Uani 1 1 d . . . . .
H10 H 0.202683 0.099476 0.732086 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3975(5) 0.1552(5) 0.6888(4) 0.0173(8) Uani 1 1 d . . . . .
H11 H 0.403881 0.062722 0.673686 0.021 Uiso 1 1 calc R U . . .
C12 C 0.8022(5) 0.3303(4) 0.5211(3) 0.0138(8) Uani 1 1 d . . . . .
C13 C 0.9484(5) 0.3475(4) 0.5586(4) 0.0163(8) Uani 1 1 d . . . . .
H13 H 0.994093 0.392657 0.634577 0.020 Uiso 1 1 calc R U . . .
C14 C 1.0285(5) 0.2999(5) 0.4869(4) 0.0176(9) Uani 1 1 d . . . . .
H14 H 1.127933 0.311095 0.512565 0.021 Uiso 1 1 calc R U . . .
C15 C 0.9592(5) 0.2360(5) 0.3776(4) 0.0173(9) Uani 1 1 d . . . . .
C16 C 0.8173(5) 0.2216(5) 0.3362(4) 0.0182(9) Uani 1 1 d . . . . .
H16 H 0.774496 0.180621 0.259996 0.022 Uiso 1 1 calc R U . . .
C17 C 0.7385(5) 0.2690(5) 0.4094(3) 0.0166(8) Uani 1 1 d . . . . .
H17 H 0.640029 0.259449 0.382929 0.020 Uiso 1 1 calc R U . . .
C18 C 0.6468(4) 0.6770(4) 0.7500(3) 0.0130(8) Uani 1 1 d . . . . .
C19 C 0.7176(5) 0.8989(4) 0.9244(3) 0.0164(8) Uani 1 1 d . . . . .
C20 C 0.8116(5) 0.9424(5) 1.0232(3) 0.0184(9) Uani 1 1 d . . . . .
H20 H 0.836543 1.030612 1.085839 0.022 Uiso 1 1 calc R U . . .
C21 C 0.8651(5) 0.8308(5) 1.0144(3) 0.0166(8) Uani 1 1 d . . . . .
C22 C 0.9721(5) 0.8265(5) 1.0995(3) 0.0202(9) Uani 1 1 d . . . . .
H22A H 0.916794 0.784693 1.144641 0.030 Uiso 1 1 calc R U . . .
H22B H 1.046896 0.927200 1.145142 0.030 Uiso 1 1 calc R U . . .
H22C H 1.023022 0.764948 1.064527 0.030 Uiso 1 1 calc R U . . .
C23 C 0.6247(6) 0.9696(5) 0.8891(4) 0.0235(10) Uani 1 1 d . . . . .
H23A H 0.658309 0.997564 0.831271 0.035 Uiso 1 1 calc R U . . .
H23B H 0.635905 1.058083 0.951044 0.035 Uiso 1 1 calc R U . . .
H23C H 0.518875 0.899509 0.861734 0.035 Uiso 1 1 calc R U . . .
C24 C 0.7991(5) -0.0206(5) 0.5963(4) 0.0225(10) Uani 1 1 d . . . . .
H24A H 0.797878 -0.096612 0.529312 0.034 Uiso 1 1 calc R U . . .
H24B H 0.759964 -0.066643 0.644711 0.034 Uiso 1 1 calc R U . . .
H24C H 0.902426 0.053398 0.632683 0.034 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C25 1.756(5) . ?
Cl2 C25 1.770(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
F1 C15 1.374(5) . ?
O1 C1 1.203(5) . ?
O2 C1 1.334(5) . ?
O2 C24 1.449(5) . ?
O3 C18 1.214(5) . ?
N1 C2 1.454(5) . ?
N1 C7 1.475(5) . ?
N1 C11 1.369(5) . ?
N2 N3 1.386(5) . ?
N2 C18 1.396(5) . ?
N2 C19 1.389(5) . ?
N3 C21 1.318(6) . ?
C1 C2 1.532(5) . ?
C2 H2 1.0000 . ?
C2 C3 1.544(5) . ?
C3 C4 1.549(5) . ?
C3 C6 1.551(5) . ?
C3 C12 1.502(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.547(5) . ?
C5 C6 1.553(5) . ?
C5 C7 1.533(5) . ?
C5 C18 1.511(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7 1.0000 . ?
C7 C8 1.505(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.343(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.442(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.351(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(6) . ?
C12 C17 1.392(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.373(6) . ?
C15 C16 1.378(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(6) . ?
C17 H17 0.9500 . ?
C19 C20 1.365(6) . ?
C19 C23 1.491(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.418(6) . ?
C21 C22 1.493(6) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
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
Cl1 C25 Cl2 111.8(3) . . ?
Cl1 C25 H25A 109.3 . . ?
Cl1 C25 H25B 109.3 . . ?
Cl2 C25 H25A 109.3 . . ?
Cl2 C25 H25B 109.3 . . ?
H25A C25 H25B 107.9 . . ?
C1 O2 C24 116.5(3) . . ?
C2 N1 C7 123.4(3) . . ?
C11 N1 C2 118.9(3) . . ?
C11 N1 C7 117.7(3) . . ?
N3 N2 C18 119.6(3) . . ?
N3 N2 C19 112.3(3) . . ?
C19 N2 C18 128.1(3) . . ?
C21 N3 N2 104.2(3) . . ?
O1 C1 O2 124.6(4) . . ?
O1 C1 C2 125.7(4) . . ?
O2 C1 C2 109.7(3) . . ?
N1 C2 C1 111.1(3) . . ?
N1 C2 H2 108.3 . . ?
N1 C2 C3 110.5(3) . . ?
C1 C2 H2 108.3 . . ?
C1 C2 C3 110.4(3) . . ?
C3 C2 H2 108.3 . . ?
C2 C3 C4 107.1(3) . . ?
C2 C3 C6 108.7(3) . . ?
C4 C3 C6 88.2(3) . . ?
C12 C3 C2 110.8(3) . . ?
C12 C3 C4 119.1(3) . . ?
C12 C3 C6 120.5(3) . . ?
C3 C4 H4A 114.3 . . ?
C3 C4 H4B 114.3 . . ?
H4A C4 H4B 111.4 . . ?
C5 C4 C3 86.3(3) . . ?
C5 C4 H4A 114.3 . . ?
C5 C4 H4B 114.3 . . ?
C4 C5 C6 88.3(3) . . ?
C7 C5 C4 110.1(3) . . ?
C7 C5 C6 108.8(3) . . ?
C18 C5 C4 115.2(3) . . ?
C18 C5 C6 121.5(3) . . ?
C18 C5 C7 110.9(3) . . ?
C3 C6 C5 86.0(3) . . ?
C3 C6 H6A 114.3 . . ?
C3 C6 H6B 114.3 . . ?
C5 C6 H6A 114.3 . . ?
C5 C6 H6B 114.3 . . ?
H6A C6 H6B 111.5 . . ?
N1 C7 C5 108.5(3) . . ?
N1 C7 H7 108.3 . . ?
N1 C7 C8 108.3(3) . . ?
C5 C7 H7 108.3 . . ?
C8 C7 C5 115.1(3) . . ?
C8 C7 H7 108.3 . . ?
C7 C8 H8 120.8 . . ?
C9 C8 C7 118.5(4) . . ?
C9 C8 H8 120.8 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 121.4 . . ?
C11 C10 C9 117.2(4) . . ?
C11 C10 H10 121.4 . . ?
N1 C11 H11 119.1 . . ?
C10 C11 N1 121.9(4) . . ?
C10 C11 H11 119.0 . . ?
C13 C12 C3 120.9(4) . . ?
C17 C12 C3 120.2(4) . . ?
C17 C12 C13 118.8(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(4) . . ?
C14 C13 H13 119.4 . . ?
C13 C14 H14 121.1 . . ?
C15 C14 C13 117.8(4) . . ?
C15 C14 H14 121.1 . . ?
F1 C15 C16 118.3(4) . . ?
C14 C15 F1 118.4(4) . . ?
C14 C15 C16 123.3(4) . . ?
C15 C16 H16 121.0 . . ?
C15 C16 C17 117.9(4) . . ?
C17 C16 H16 121.0 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(4) . . ?
C16 C17 H17 119.6 . . ?
O3 C18 N2 120.6(4) . . ?
O3 C18 C5 122.1(4) . . ?
N2 C18 C5 117.3(3) . . ?
N2 C19 C23 125.0(4) . . ?
C20 C19 N2 104.9(4) . . ?
C20 C19 C23 130.0(4) . . ?
C19 C20 H20 126.5 . . ?
C19 C20 C21 106.9(4) . . ?
C21 C20 H20 126.5 . . ?
N3 C21 C20 111.7(4) . . ?
N3 C21 C22 120.3(4) . . ?
C20 C21 C22 128.0(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
F1 C15 C16 C17 177.3(4) . . . . ?
O1 C1 C2 N1 -40.0(6) . . . . ?
O1 C1 C2 C3 82.9(5) . . . . ?
O2 C1 C2 N1 141.1(3) . . . . ?
O2 C1 C2 C3 -96.0(4) . . . . ?
N1 C2 C3 C4 -45.4(4) . . . . ?
N1 C2 C3 C6 48.7(4) . . . . ?
N1 C2 C3 C12 -176.8(3) . . . . ?
N1 C7 C8 C9 37.3(5) . . . . ?
N2 N3 C21 C20 1.0(5) . . . . ?
N2 N3 C21 C22 -179.0(4) . . . . ?
N2 C19 C20 C21 0.0(5) . . . . ?
N3 N2 C18 O3 -167.6(4) . . . . ?
N3 N2 C18 C5 14.0(5) . . . . ?
N3 N2 C19 C20 0.6(5) . . . . ?
N3 N2 C19 C23 -176.3(4) . . . . ?
C1 C2 C3 C4 -168.6(3) . . . . ?
C1 C2 C3 C6 -74.6(4) . . . . ?
C1 C2 C3 C12 60.0(4) . . . . ?
C2 N1 C7 C5 7.4(5) . . . . ?
C2 N1 C7 C8 133.0(4) . . . . ?
C2 N1 C11 C10 -154.6(4) . . . . ?
C2 C3 C4 C5 84.1(3) . . . . ?
C2 C3 C6 C5 -82.7(3) . . . . ?
C2 C3 C12 C13 -96.7(4) . . . . ?
C2 C3 C12 C17 80.0(4) . . . . ?
C3 C4 C5 C6 24.9(3) . . . . ?
C3 C4 C5 C7 -84.5(3) . . . . ?
C3 C4 C5 C18 149.2(3) . . . . ?
C3 C12 C13 C14 174.3(4) . . . . ?
C3 C12 C17 C16 -174.9(4) . . . . ?
C4 C3 C6 C5 24.8(3) . . . . ?
C4 C3 C12 C13 138.4(4) . . . . ?
C4 C3 C12 C17 -44.9(5) . . . . ?
C4 C5 C6 C3 -24.9(3) . . . . ?
C4 C5 C7 N1 42.8(4) . . . . ?
C4 C5 C7 C8 -78.6(4) . . . . ?
C4 C5 C18 O3 21.5(6) . . . . ?
C4 C5 C18 N2 -160.1(3) . . . . ?
C5 C7 C8 C9 159.0(4) . . . . ?
C6 C3 C4 C5 -24.9(3) . . . . ?
C6 C3 C12 C13 31.7(6) . . . . ?
C6 C3 C12 C17 -151.6(4) . . . . ?
C6 C5 C7 N1 -52.4(4) . . . . ?
C6 C5 C7 C8 -173.8(3) . . . . ?
C6 C5 C18 O3 125.9(4) . . . . ?
C6 C5 C18 N2 -55.8(5) . . . . ?
C7 N1 C2 C1 117.1(4) . . . . ?
C7 N1 C2 C3 -5.8(5) . . . . ?
C7 N1 C11 C10 21.8(6) . . . . ?
C7 C5 C6 C3 85.8(3) . . . . ?
C7 C5 C18 O3 -104.4(4) . . . . ?
C7 C5 C18 N2 73.9(4) . . . . ?
C7 C8 C9 C10 -10.0(6) . . . . ?
C8 C9 C10 C11 -15.4(7) . . . . ?
C9 C10 C11 N1 9.4(7) . . . . ?
C11 N1 C2 C1 -66.8(5) . . . . ?
C11 N1 C2 C3 170.4(4) . . . . ?
C11 N1 C7 C5 -168.8(4) . . . . ?
C11 N1 C7 C8 -43.2(5) . . . . ?
C12 C3 C4 C5 -149.3(4) . . . . ?
C12 C3 C6 C5 148.0(4) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C12 C17 C16 1.9(6) . . . . ?
C13 C14 C15 F1 -177.8(4) . . . . ?
C13 C14 C15 C16 2.2(6) . . . . ?
C14 C15 C16 C17 -2.7(6) . . . . ?
C15 C16 C17 C12 0.6(6) . . . . ?
C17 C12 C13 C14 -2.4(6) . . . . ?
C18 N2 N3 C21 175.7(4) . . . . ?
C18 N2 C19 C20 -175.7(4) . . . . ?
C18 N2 C19 C23 7.4(7) . . . . ?
C18 C5 C6 C3 -143.6(4) . . . . ?
C18 C5 C7 N1 171.5(3) . . . . ?
C18 C5 C7 C8 50.0(5) . . . . ?
C19 N2 N3 C21 -1.0(4) . . . . ?
C19 N2 C18 O3 8.5(6) . . . . ?
C19 N2 C18 C5 -169.8(4) . . . . ?
C19 C20 C21 N3 -0.6(5) . . . . ?
C19 C20 C21 C22 179.3(4) . . . . ?
C23 C19 C20 C21 176.6(4) . . . . ?
C24 O2 C1 O1 -3.3(6) . . . . ?
C24 O2 C1 C2 175.6(3) . . . . ?

_olex2_date_sample_data_collection 2024-06-03
_olex2_exptl_crystal_mounting_method 'mounted in a polyimide loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.320
_oxdiff_exptl_absorpt_empirical_full_min 0.864
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.738(4)
2 0.262(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_leitch001
_database_code_depnum_ccdc_archive 'CCDC 2374389'
loop_
_audit_author_name
_audit_author_address
'Nathan D. Schley'
;Vanderbilt University
United States of America
;
_audit_update_record             
;
2024-07-30 deposited with the CCDC.	2024-10-08 downloaded from the CCDC.
;
_audit_creation_date             2024-07-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 N O4'
_chemical_formula_sum            'C20 H23 N O4'
_chemical_formula_weight         341.39
_chemical_melting_point          ?
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      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                   5.8883(2)
_cell_length_b                   10.8918(3)
_cell_length_c                   14.0443(4)
_cell_angle_alpha                75.0940(10)
_cell_angle_beta                 88.4840(10)
_cell_angle_gamma                89.5780(10)
_cell_volume                     870.11(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9929
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      3.26
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.736
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6716
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0823 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8918.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18254
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.415
_diffrn_reflns_theta_min         3.257
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           0.59
_diffrn_source_power             0.026373
_diffrn_source_voltage           44.7
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2899
_reflns_number_total             3161
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.037
_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)+(0.0449P)²+0.4366P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          'Refined without additional restraints.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(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
O1 O 0.1656(2) 0.59992(10) 0.56046(7) 0.0337(3) Uani 1 1 d . . . . .
O2 O -0.02442(18) 0.78330(10) 0.51786(7) 0.0290(3) Uani 1 1 d . . . . .
O3 O 0.45905(16) 0.82547(9) 0.03259(7) 0.0236(2) Uani 1 1 d . . . . .
O4 O 0.10147(16) 0.83272(9) 0.08955(7) 0.0205(2) Uani 1 1 d . . . . .
N1 N 0.30169(19) 0.90110(10) 0.24682(8) 0.0169(2) Uani 1 1 d . . . . .
C1 C 0.1203(2) 0.69616(13) 0.49999(10) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.2137(2) 0.73086(12) 0.39555(9) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.4151(2) 0.65026(12) 0.37343(9) 0.0176(3) Uani 1 1 d . . . . .
H3A H 0.414628 0.563135 0.413337 0.021 Uiso 1 1 calc R U . . .
H3B H 0.562521 0.689622 0.372782 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3135(2) 0.66796(12) 0.27000(9) 0.0160(3) Uani 1 1 d . . . . .
C5 C 0.0773(2) 0.68346(12) 0.31820(9) 0.0169(3) Uani 1 1 d . . . . .
H5A H -0.003695 0.604357 0.344881 0.020 Uiso 1 1 calc R U . . .
H5B H -0.019446 0.747358 0.277651 0.020 Uiso 1 1 calc R U . . .
C6 C 0.2653(2) 0.87333(12) 0.35423(9) 0.0164(3) Uani 1 1 d . . . . .
H6 H 0.130088 0.920481 0.366627 0.020 Uiso 1 1 calc R U . . .
C7 C 0.4595(2) 0.91437(13) 0.40683(10) 0.0203(3) Uani 1 1 d . . . . .
H7 H 0.457014 0.890044 0.475358 0.024 Uiso 1 1 calc R U . . .
C8 C 0.6337(2) 0.98325(13) 0.36070(10) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.749277 1.003456 0.397902 0.026 Uiso 1 1 calc R U . . .
C9 C 0.6501(2) 1.02952(13) 0.25070(10) 0.0236(3) Uani 1 1 d . . . . .
H9A H 0.757169 0.977356 0.224826 0.028 Uiso 1 1 calc R U . . .
H9B H 0.704970 1.116408 0.232087 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4165(2) 1.02304(12) 0.20721(10) 0.0210(3) Uani 1 1 d . . . . .
H10A H 0.321573 1.090269 0.220401 0.025 Uiso 1 1 calc R U . . .
H10B H 0.433915 1.038099 0.136272 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3957(2) 0.79944(12) 0.20703(9) 0.0161(3) Uani 1 1 d . . . . .
H11 H 0.561819 0.802351 0.208793 0.019 Uiso 1 1 calc R U . . .
C12 C 0.3260(2) 0.82177(12) 0.10001(10) 0.0168(3) Uani 1 1 d . . . . .
C13 C 0.3501(2) 0.56455(12) 0.21764(9) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.5558(2) 0.49904(13) 0.22562(10) 0.0208(3) Uani 1 1 d . . . . .
H14 H 0.668394 0.517535 0.265008 0.025 Uiso 1 1 calc R U . . .
C15 C 0.5937(2) 0.40639(13) 0.17519(11) 0.0249(3) Uani 1 1 d . . . . .
H15 H 0.731511 0.363158 0.181192 0.030 Uiso 1 1 calc R U . . .
C16 C 0.4283(3) 0.37768(13) 0.11601(11) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.455022 0.316427 0.081541 0.030 Uiso 1 1 calc R U . . .
C17 C 0.2223(3) 0.44147(13) 0.10885(10) 0.0242(3) Uani 1 1 d . . . . .
H17 H 0.109581 0.422123 0.069891 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1829(2) 0.53400(13) 0.15934(10) 0.0205(3) Uani 1 1 d . . . . .
H18 H 0.043760 0.575882 0.154166 0.025 Uiso 1 1 calc R U . . .
C19 C -0.1323(3) 0.75240(16) 0.61475(11) 0.0365(4) Uani 1 1 d . . . . .
H19A H -0.226187 0.678634 0.622507 0.055 Uiso 1 1 calc R U . . .
H19B H -0.224206 0.822680 0.622123 0.055 Uiso 1 1 calc R U . . .
H19C H -0.017979 0.735359 0.663956 0.055 Uiso 1 1 calc R U . . .
C20 C 0.0247(3) 0.84231(15) -0.00944(10) 0.0271(3) Uani 1 1 d . . . . .
H20A H 0.074948 0.921460 -0.052411 0.041 Uiso 1 1 calc R U . . .
H20B H -0.138221 0.838608 -0.008706 0.041 Uiso 1 1 calc R U . . .
H20C H 0.086498 0.773220 -0.032695 0.041 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 C1 1.2004(17) . ?
O2 C1 1.3378(17) . ?
O2 C19 1.4456(17) . ?
O3 C12 1.2056(16) . ?
O4 C12 1.3352(16) . ?
O4 C20 1.4513(16) . ?
N1 C6 1.4704(16) . ?
N1 C10 1.4640(16) . ?
N1 C11 1.4621(16) . ?
C1 C2 1.5071(18) . ?
C2 C3 1.5425(17) . ?
C2 C5 1.5594(17) . ?
C2 C6 1.5399(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5507(17) . ?
C4 C5 1.5577(17) . ?
C4 C11 1.5502(17) . ?
C4 C13 1.5066(17) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6 0.9800 . ?
C6 C7 1.5084(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.327(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.4974(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.530(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11 0.9800 . ?
C11 C12 1.5263(17) . ?
C13 C14 1.3937(19) . ?
C13 C18 1.3921(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.3877(19) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.3885(19) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C19 115.63(11) . . ?
C12 O4 C20 114.94(10) . . ?
C10 N1 C6 111.83(10) . . ?
C11 N1 C6 117.33(10) . . ?
C11 N1 C10 113.00(10) . . ?
O1 C1 O2 123.15(12) . . ?
O1 C1 C2 124.28(12) . . ?
O2 C1 C2 112.55(11) . . ?
C1 C2 C3 116.18(11) . . ?
C1 C2 C5 116.73(11) . . ?
C1 C2 C6 114.16(10) . . ?
C3 C2 C5 87.65(9) . . ?
C6 C2 C3 110.29(10) . . ?
C6 C2 C5 108.90(10) . . ?
C2 C3 H3A 114.3 . . ?
C2 C3 H3B 114.3 . . ?
C2 C3 C4 86.42(9) . . ?
H3A C3 H3B 111.4 . . ?
C4 C3 H3A 114.3 . . ?
C4 C3 H3B 114.3 . . ?
C3 C4 C5 87.42(9) . . ?
C11 C4 C3 106.49(10) . . ?
C11 C4 C5 109.14(10) . . ?
C13 C4 C3 118.51(11) . . ?
C13 C4 C5 119.98(11) . . ?
C13 C4 C11 112.38(10) . . ?
C2 C5 H5A 114.4 . . ?
C2 C5 H5B 114.4 . . ?
C4 C5 C2 85.59(9) . . ?
C4 C5 H5A 114.4 . . ?
C4 C5 H5B 114.4 . . ?
H5A C5 H5B 111.5 . . ?
N1 C6 C2 109.35(10) . . ?
N1 C6 H6 107.4 . . ?
N1 C6 C7 113.60(11) . . ?
C2 C6 H6 107.4 . . ?
C7 C6 C2 111.28(10) . . ?
C7 C6 H6 107.4 . . ?
C6 C7 H7 118.2 . . ?
C8 C7 C6 123.61(12) . . ?
C8 C7 H7 118.2 . . ?
C7 C8 H8 118.9 . . ?
C7 C8 C9 122.14(13) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C8 C9 C10 109.72(11) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
N1 C10 C9 113.33(11) . . ?
N1 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C9 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 C4 110.55(10) . . ?
N1 C11 H11 108.7 . . ?
N1 C11 C12 108.96(10) . . ?
C4 C11 H11 108.7 . . ?
C12 C11 C4 111.23(10) . . ?
C12 C11 H11 108.7 . . ?
O3 C12 O4 123.65(12) . . ?
O3 C12 C11 123.55(12) . . ?
O4 C12 C11 112.76(11) . . ?
C14 C13 C4 120.01(12) . . ?
C18 C13 C4 121.23(12) . . ?
C18 C13 C14 118.75(12) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.43(13) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.64(13) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.12(13) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 H17 119.7 . . ?
C16 C17 C18 120.56(13) . . ?
C18 C17 H17 119.7 . . ?
C13 C18 H18 119.8 . . ?
C17 C18 C13 120.48(13) . . ?
C17 C18 H18 119.8 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C1 C2 C3 -12.9(2) . . . . ?
O1 C1 C2 C5 88.40(17) . . . . ?
O1 C1 C2 C6 -143.03(14) . . . . ?
O2 C1 C2 C3 168.66(11) . . . . ?
O2 C1 C2 C5 -90.01(14) . . . . ?
O2 C1 C2 C6 38.56(16) . . . . ?
N1 C6 C7 C8 8.17(18) . . . . ?
N1 C11 C12 O3 126.88(13) . . . . ?
N1 C11 C12 O4 -55.11(13) . . . . ?
C1 C2 C3 C4 145.57(11) . . . . ?
C1 C2 C5 C4 -144.97(11) . . . . ?
C1 C2 C6 N1 -166.49(10) . . . . ?
C1 C2 C6 C7 67.19(14) . . . . ?
C2 C3 C4 C5 -26.82(9) . . . . ?
C2 C3 C4 C11 82.39(11) . . . . ?
C2 C3 C4 C13 -149.83(11) . . . . ?
C2 C6 C7 C8 132.11(14) . . . . ?
C3 C2 C5 C4 -26.69(9) . . . . ?
C3 C2 C6 N1 60.55(13) . . . . ?
C3 C2 C6 C7 -65.76(13) . . . . ?
C3 C4 C5 C2 26.54(9) . . . . ?
C3 C4 C11 N1 -64.63(12) . . . . ?
C3 C4 C11 C12 174.19(10) . . . . ?
C3 C4 C13 C14 -37.07(17) . . . . ?
C3 C4 C13 C18 144.11(12) . . . . ?
C4 C11 C12 O3 -111.00(14) . . . . ?
C4 C11 C12 O4 67.01(13) . . . . ?
C4 C13 C14 C15 -177.97(12) . . . . ?
C4 C13 C18 C17 177.75(12) . . . . ?
C5 C2 C3 C4 26.79(9) . . . . ?
C5 C2 C6 N1 -34.06(13) . . . . ?
C5 C2 C6 C7 -160.37(10) . . . . ?
C5 C4 C11 N1 28.41(13) . . . . ?
C5 C4 C11 C12 -92.77(12) . . . . ?
C5 C4 C13 C14 -141.80(13) . . . . ?
C5 C4 C13 C18 39.39(18) . . . . ?
C6 N1 C10 C9 59.80(14) . . . . ?
C6 N1 C11 C4 32.85(15) . . . . ?
C6 N1 C11 C12 155.37(11) . . . . ?
C6 C2 C3 C4 -82.51(11) . . . . ?
C6 C2 C5 C4 83.97(11) . . . . ?
C6 C7 C8 C9 1.5(2) . . . . ?
C7 C8 C9 C10 17.81(18) . . . . ?
C8 C9 C10 N1 -48.25(15) . . . . ?
C10 N1 C6 C2 -162.86(10) . . . . ?
C10 N1 C6 C7 -37.89(14) . . . . ?
C10 N1 C11 C4 165.24(10) . . . . ?
C10 N1 C11 C12 -72.24(13) . . . . ?
C11 N1 C6 C2 -29.95(15) . . . . ?
C11 N1 C6 C7 95.03(13) . . . . ?
C11 N1 C10 C9 -75.23(13) . . . . ?
C11 C4 C5 C2 -80.02(11) . . . . ?
C11 C4 C13 C14 87.89(14) . . . . ?
C11 C4 C13 C18 -90.93(14) . . . . ?
C13 C4 C5 C2 148.25(12) . . . . ?
C13 C4 C11 N1 164.05(10) . . . . ?
C13 C4 C11 C12 42.86(14) . . . . ?
C13 C14 C15 C16 0.1(2) . . . . ?
C14 C13 C18 C17 -1.1(2) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C13 0.3(2) . . . . ?
C18 C13 C14 C15 0.9(2) . . . . ?
C19 O2 C1 O1 -2.3(2) . . . . ?
C19 O2 C1 C2 176.11(13) . . . . ?
C20 O4 C12 O3 3.44(18) . . . . ?
C20 O4 C12 C11 -174.57(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
