# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2421901'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2023-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H28 N, C6 H6, I'
_chemical_formula_sum            'C25 H34 I N'
_chemical_formula_weight         475.43
_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'
I I -0.3257 6.8362 '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'

_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        P21/c
_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                   17.4227(6)
_cell_length_b                   9.8519(3)
_cell_length_c                   13.1335(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.198(3)
_cell_angle_gamma                90
_cell_volume                     2236.54(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7982
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      76.4330
_cell_measurement_theta_min      2.6510
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.286
_exptl_absorpt_coefficient_mu    11.293
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.464
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             976
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -8 0.0212
0 0 8 0.0212
-1 -6 0 0.0768
1 6 1 0.0675
-11 0 0 0.0010
11 0 0 0.0050

_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.006
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
-0.1722 0.1083 -8.4389 -0.4869 0.0096 0.8734
0.1722 -0.1083 8.4389 0.4869 -0.0096 -0.8734
-0.9371 -6.3687 -0.2056 0.8640 -0.0232 0.5030
0.9466 6.3298 0.8845 -0.8207 0.0223 -0.5710
-11.2539 0.1373 0.2328 0.0244 0.9909 0.1325
11.2539 -0.1373 -0.2328 -0.0244 -0.9909 -0.1325

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18421
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.429
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -11.00  14.00   0.50    0.20    --   51.64 -85.00 113.00   50
  2  ω   -105.00 -80.00   0.50    0.80    --  -87.58 -85.00 113.00   50
  3  ω   -152.00-125.00   0.50    0.80    --  -87.58 -85.00 113.00   54
  4  ω    -69.00 -44.00   0.50    0.80    --  -87.58  85.00-126.00   50
  5  ω     37.00 127.00   0.50    0.80    --  102.12 -85.00 113.00  180
  6  ω     86.00 127.00   0.50    0.80    --  102.12  85.00-126.00   82
  7  ω    -80.00 -37.00   0.50    0.20    --  -51.51  85.00-126.00   86
  8  ω   -122.00 -75.00   0.50    0.20    --  -51.51-125.00 -90.00   94
  9  ω     -2.00  25.00   0.50    0.20    --  -51.51  19.00-180.00   54
 10  ω    -27.00  15.00   0.50    0.20    --  -51.51  85.00-126.00   84
 11  ω    -21.00  29.00   0.50    0.20    --   51.64 -19.00-180.00  100
 12  ω     22.00  76.00   0.50    0.20    --   51.64 -85.00 113.00  108
 13  ω    -53.00 -23.00   0.50    0.80    --  -87.58  57.00-180.00   60
 14  ω    -47.00 -16.00   0.50    0.80    --  -87.58  57.00-150.00   62
 15  ω   -106.00 -21.00   0.50    0.80    --  -87.58  77.00  60.00  170
 16  ω     25.00  50.00   0.50    0.80    --  102.12 -38.00 150.00   50
 17  ω     31.00  67.00   0.50    0.80    --  102.12 -57.00 -60.00   72
 18  ω     37.00  63.00   0.50    0.80    --  102.12 -57.00 150.00   52
 19  ω     25.00  52.00   0.50    0.80    --  102.12 -38.00  30.00   54
 20  ω     36.00  64.00   0.50    0.80    --  102.12 -77.00 -90.00   56
 21  ω     25.00  50.00   0.50    0.80    --  102.12 -38.00 120.00   50
 22  ω     58.00  93.00   0.50    0.80    --  102.12-125.00 -90.00   70
 23  ω     71.00 169.00   0.50    0.80    --  102.12  19.00 150.00  196
 24  ω     26.00  51.00   0.50    0.80    --  102.12 -38.00-180.00   50
 25  ω     47.00  74.00   0.50    0.80    --  102.12 -57.00   0.00   54
 26  ω     29.00  62.00   0.50    0.80    --  102.12 -57.00 120.00   66
 27  ω     31.00  73.00   0.50    0.80    --  102.12 -57.00-180.00   84
 28  ω     74.00 114.00   0.50    0.80    --  102.12 -77.00 -90.00   80
 29  ω     26.00  51.00   0.50    0.80    --  102.12 -38.00 -30.00   50
 30  ω     36.00  80.00   0.50    0.80    --  102.12 -99.00-180.00   88
 31  ω     29.00  61.00   0.50    0.80    --  102.12 -57.00 -90.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0026841000
_diffrn_orient_matrix_UB_12      -0.1370738000
_diffrn_orient_matrix_UB_13      0.0559904000
_diffrn_orient_matrix_UB_21      -0.0878288000
_diffrn_orient_matrix_UB_22      0.0165328000
_diffrn_orient_matrix_UB_23      0.0008663000
_diffrn_orient_matrix_UB_31      -0.0148192000
_diffrn_orient_matrix_UB_32      -0.0734336000
_diffrn_orient_matrix_UB_33      -0.1041390000
_diffrn_oxdiff_digest_frames     
;
017b048c49c7c6198a0398e9a4895a7fec024202c6d
;
_diffrn_oxdiff_digest_hkl        
;
01cf682ee28a7068b93845f84eb6973df1fa12
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3608
_reflns_number_total             4543
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         2.097
_refine_diff_density_min         -1.897
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         4543
_refine_ls_number_restraints     126
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0522
_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)+(0.0843P)²+3.4224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1468
_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. Rigid body (RIGU) restrains
 C12, C12A, C13, C13A, C14, C14A, C15, C15A, C16, C16A, C17, C17A, C18, C18A,
 C19, C19A, C20, C20A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=
 Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=
 Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18C)=Sof(H18D)=Sof(C19A)=Sof(H19A)=
 Sof(C20A)=Sof(H20C)=Sof(H20D)=1-FVAR(1)
 Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14A)=
 Sof(H14B)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17)=
 Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C15(H15), C15A(H15A), C17(H17), C17A(H17A), C19(H19), C19A(H19A)
4.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12C,H12D), C13(H13A,H13B), C13A(H13C,H13D), C14(H14A,
 H14B), C14A(H14C,H14D), C16(H16A,H16B), C16A(H16C,H16D), C18(H18A,H18B),
 C18A(H18C,H18D), C20(H20A,H20B), C20A(H20C,H20D)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C101(H101), C102(H102), C103(H103),
 C104(H104), C105(H105), C106(H106)
4.d 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
I1 I 0.40893(2) 0.16546(3) 0.38758(2) 0.03375(15) Uani 1 1 d . . . . .
N1 N 0.5692(3) 0.3415(4) 0.6650(3) 0.0292(9) Uani 1 1 d . . . . .
C2 C 0.6003(4) 0.4173(6) 0.7607(4) 0.0346(12) Uani 1 1 d . . . . .
H2A H 0.6503 0.3788 0.7888 0.052 Uiso 1 1 calc GR . . . .
H2B H 0.5639 0.4091 0.8115 0.052 Uiso 1 1 calc GR . . . .
H2C H 0.6068 0.5132 0.7442 0.052 Uiso 1 1 calc GR . . . .
C3 C 0.4959(3) 0.4089(6) 0.6194(4) 0.0327(11) Uani 1 1 d . . . . .
H3A H 0.5060 0.5050 0.6069 0.049 Uiso 1 1 calc GR . . . .
H3B H 0.4571 0.4013 0.6670 0.049 Uiso 1 1 calc GR . . . .
H3C H 0.4766 0.3646 0.5544 0.049 Uiso 1 1 calc GR . . . .
C4 C 0.5499(4) 0.2005(6) 0.6944(5) 0.0439(16) Uani 1 1 d . . . . .
H4A H 0.5267 0.1512 0.6333 0.066 Uiso 1 1 calc GR . . . .
H4B H 0.5130 0.2037 0.7450 0.066 Uiso 1 1 calc GR . . . .
H4C H 0.5971 0.1539 0.7241 0.066 Uiso 1 1 calc GR . . . .
C5 C 0.6291(3) 0.3426(5) 0.5894(4) 0.0282(11) Uani 1 1 d . . . . .
C6 C 0.6549(4) 0.4674(5) 0.5596(4) 0.0325(12) Uani 1 1 d . . . . .
H6 H 0.6343 0.5490 0.5835 0.039 Uiso 1 1 calc R . . . .
C7 C 0.7112(3) 0.4710(5) 0.4945(4) 0.0326(12) Uani 1 1 d . . . . .
H7 H 0.7286 0.5568 0.4733 0.039 Uiso 1 1 calc R . . . .
C8 C 0.7435(3) 0.3542(5) 0.4586(4) 0.0264(10) Uani 1 1 d . . . . .
C9 C 0.7142(3) 0.2314(5) 0.4887(3) 0.0261(10) Uani 1 1 d . . . . .
H9 H 0.7340 0.1493 0.4644 0.031 Uiso 1 1 calc R . . . .
C10 C 0.6568(3) 0.2246(5) 0.5535(4) 0.0296(11) Uani 1 1 d . . . . .
H10 H 0.6372 0.1394 0.5722 0.035 Uiso 1 1 calc R . . . .
C11 C 0.8102(3) 0.3618(5) 0.3913(4) 0.0274(11) Uani 1 1 d . . . . .
C12 C 0.8877(4) 0.3544(7) 0.4604(5) 0.0302(16) Uani 0.748(9) 1 d . U P A 1
H12A H 0.8902 0.2687 0.5001 0.036 Uiso 0.748(9) 1 calc R . P A 1
H12B H 0.8912 0.4307 0.5098 0.036 Uiso 0.748(9) 1 calc R . P A 1
C12A C 0.8675(12) 0.466(2) 0.4324(15) 0.027(4) Uani 0.252(9) 1 d . U P A 2
H12C H 0.8892 0.4419 0.5034 0.032 Uiso 0.252(9) 1 calc R . P A 2
H12D H 0.8415 0.5553 0.4345 0.032 Uiso 0.252(9) 1 calc R . P A 2
C13 C 0.8098(4) 0.4997(8) 0.3298(5) 0.0307(15) Uani 0.748(9) 1 d . U P A 1
H13A H 0.7608 0.5082 0.2832 0.037 Uiso 0.748(9) 1 calc R . P A 1
H13B H 0.8133 0.5770 0.3783 0.037 Uiso 0.748(9) 1 calc R . P A 1
C13A C 0.7771(12) 0.3798(19) 0.2871(14) 0.023(4) Uani 0.252(9) 1 d . U P A 2
H13C H 0.7480 0.4663 0.2803 0.027 Uiso 0.252(9) 1 calc R . P A 2
H13D H 0.7404 0.3049 0.2669 0.027 Uiso 0.252(9) 1 calc R . P A 2
C14 C 0.8057(5) 0.2464(8) 0.3127(6) 0.0358(17) Uani 0.748(9) 1 d . U P A 1
H14A H 0.7566 0.2538 0.2661 0.043 Uiso 0.748(9) 1 calc R . P A 1
H14B H 0.8056 0.1582 0.3489 0.043 Uiso 0.748(9) 1 calc R . P A 1
C14A C 0.8544(13) 0.219(2) 0.4035(16) 0.030(4) Uani 0.252(9) 1 d . U P A 2
H14C H 0.8773 0.2048 0.4756 0.036 Uiso 0.252(9) 1 calc R . P A 2
H14D H 0.8178 0.1434 0.3837 0.036 Uiso 0.252(9) 1 calc R . P A 2
C15 C 0.9570(6) 0.3607(9) 0.3981(6) 0.0326(16) Uani 0.748(9) 1 d . U P A 1
H15 H 1.0067 0.3545 0.4450 0.039 Uiso 0.748(9) 1 calc R . P A 1
C15A C 0.9325(15) 0.476(3) 0.3655(19) 0.032(4) Uani 0.252(9) 1 d . U P A 2
H15A H 0.9697 0.5500 0.3898 0.038 Uiso 0.252(9) 1 calc R . P A 2
C16 C 0.9539(5) 0.4937(9) 0.3369(6) 0.0345(16) Uani 0.748(9) 1 d . U P A 1
H16A H 0.9586 0.5717 0.3847 0.041 Uiso 0.748(9) 1 calc R . P A 1
H16B H 0.9978 0.4971 0.2958 0.041 Uiso 0.748(9) 1 calc R . P A 1
C16A C 0.8974(17) 0.499(3) 0.250(2) 0.030(4) Uani 0.252(9) 1 d . U P A 2
H16C H 0.8698 0.5866 0.2432 0.036 Uiso 0.252(9) 1 calc R . P A 2
H16D H 0.9395 0.5009 0.2062 0.036 Uiso 0.252(9) 1 calc R . P A 2
C17 C 0.8789(6) 0.5033(11) 0.2668(6) 0.0312(17) Uani 0.748(9) 1 d . U P A 1
H17 H 0.8777 0.5909 0.2282 0.037 Uiso 0.748(9) 1 calc R . P A 1
C17A C 0.8404(15) 0.382(2) 0.2156(18) 0.029(3) Uani 0.252(9) 1 d . U P A 2
H17A H 0.8171 0.3952 0.1428 0.035 Uiso 0.252(9) 1 calc R . P A 2
C18 C 0.8723(6) 0.3859(9) 0.1906(6) 0.0372(16) Uani 0.748(9) 1 d . U P A 1
H18A H 0.9154 0.3901 0.1482 0.045 Uiso 0.748(9) 1 calc R . P A 1
H18B H 0.8230 0.3932 0.1443 0.045 Uiso 0.748(9) 1 calc R . P A 1
C18A C 0.886(2) 0.250(4) 0.226(2) 0.033(4) Uani 0.252(9) 1 d . U P A 2
H18C H 0.8518 0.1737 0.2001 0.040 Uiso 0.252(9) 1 calc R . P A 2
H18D H 0.9291 0.2546 0.1839 0.040 Uiso 0.252(9) 1 calc R . P A 2
C19 C 0.8749(7) 0.2506(12) 0.2486(7) 0.0351(19) Uani 0.748(9) 1 d . U P A 1
H19 H 0.8715 0.1730 0.1991 0.042 Uiso 0.748(9) 1 calc R . P A 1
C19A C 0.9174(17) 0.222(3) 0.3333(19) 0.035(4) Uani 0.252(9) 1 d . U P A 2
H19A H 0.9453 0.1332 0.3373 0.043 Uiso 0.252(9) 1 calc R . P A 2
C20 C 0.9501(6) 0.2421(8) 0.3224(6) 0.0344(16) Uani 0.748(9) 1 d . U P A 1
H20A H 0.9513 0.1555 0.3609 0.041 Uiso 0.748(9) 1 calc R . P A 1
H20B H 0.9948 0.2431 0.2827 0.041 Uiso 0.748(9) 1 calc R . P A 1
C20A C 0.9731(17) 0.334(3) 0.373(2) 0.034(4) Uani 0.252(9) 1 d . U P A 2
H20C H 1.0171 0.3348 0.3316 0.041 Uiso 0.252(9) 1 calc R . P A 2
H20D H 0.9939 0.3148 0.4448 0.041 Uiso 0.252(9) 1 calc R . P A 2
C101 C 0.7911(4) 0.8561(6) 0.4846(5) 0.0426(14) Uani 1 1 d . . . . .
H101 H 0.7715 0.8553 0.5490 0.051 Uiso 1 1 calc R . . . .
C102 C 0.7408(4) 0.8448(6) 0.3945(6) 0.0441(15) Uani 1 1 d . . . . .
H102 H 0.6868 0.8354 0.3964 0.053 Uiso 1 1 calc R . . . .
C103 C 0.7711(4) 0.8476(6) 0.3004(5) 0.0448(15) Uani 1 1 d . . . . .
H103 H 0.7374 0.8389 0.2380 0.054 Uiso 1 1 calc R . . . .
C104 C 0.8494(5) 0.8627(6) 0.2981(5) 0.0461(16) Uani 1 1 d . . . . .
H104 H 0.8697 0.8665 0.2342 0.055 Uiso 1 1 calc R . . . .
C105 C 0.8981(4) 0.8723(7) 0.3884(6) 0.0492(17) Uani 1 1 d . . . . .
H105 H 0.9522 0.8816 0.3869 0.059 Uiso 1 1 calc R . . . .
C106 C 0.8690(4) 0.8685(7) 0.4809(5) 0.0475(16) Uani 1 1 d . . . . .
H106 H 0.9033 0.8744 0.5430 0.057 Uiso 1 1 calc R . . . .


_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
N1 C2 1.503(7) . ?
N1 C3 1.496(7) . ?
N1 C4 1.492(7) . ?
N1 C5 1.527(7) . ?
C5 C6 1.382(7) . ?
C5 C10 1.365(7) . ?
C6 C7 1.381(8) . ?
C7 C8 1.389(7) . ?
C8 C9 1.390(7) . ?
C8 C11 1.548(7) . ?
C9 C10 1.393(7) . ?
C11 C12 1.531(9) . ?
C11 C12A 1.487(19) . ?
C11 C13 1.581(9) . ?
C11 C13A 1.43(2) . ?
C11 C14 1.531(9) . ?
C11 C14A 1.60(2) . ?
C12 C15 1.542(12) . ?
C12A C15A 1.52(3) . ?
C13 C17 1.543(11) . ?
C13A C17A 1.54(3) . ?
C14 C19 1.556(12) . ?
C14A C19A 1.52(3) . ?
C15 C16 1.535(12) . ?
C15 C20 1.529(11) . ?
C15A C16A 1.58(4) . ?
C15A C20A 1.57(4) . ?
C16 C17 1.504(14) . ?
C16A C17A 1.55(4) . ?
C17 C18 1.525(13) . ?
C17A C18A 1.52(4) . ?
C18 C19 1.534(15) . ?
C18A C19A 1.47(4) . ?
C19 C20 1.532(15) . ?
C19A C20A 1.51(4) . ?
C101 C102 1.386(10) . ?
C101 C106 1.370(10) . ?
C102 C103 1.404(10) . ?
C103 C104 1.378(11) . ?
C104 C105 1.372(10) . ?
C105 C106 1.375(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
C2 N1 C5 109.7(4) . . ?
C3 N1 C2 108.3(4) . . ?
C3 N1 C5 110.8(4) . . ?
C4 N1 C2 108.4(4) . . ?
C4 N1 C3 107.9(5) . . ?
C4 N1 C5 111.7(4) . . ?
C6 C5 N1 117.6(4) . . ?
C10 C5 N1 121.2(4) . . ?
C10 C5 C6 121.2(5) . . ?
C7 C6 C5 118.7(5) . . ?
C6 C7 C8 122.5(5) . . ?
C7 C8 C9 116.5(5) . . ?
C7 C8 C11 121.2(5) . . ?
C9 C8 C11 122.2(4) . . ?
C8 C9 C10 122.2(5) . . ?
C5 C10 C9 118.9(5) . . ?
C8 C11 C13 112.2(5) . . ?
C8 C11 C14A 106.6(8) . . ?
C12 C11 C8 109.2(4) . . ?
C12 C11 C13 106.9(5) . . ?
C12A C11 C8 110.1(8) . . ?
C12A C11 C14A 106.3(13) . . ?
C13A C11 C8 108.1(9) . . ?
C13A C11 C12A 115.7(11) . . ?
C13A C11 C14A 109.6(11) . . ?
C14 C11 C8 111.7(5) . . ?
C14 C11 C12 109.4(5) . . ?
C14 C11 C13 107.3(5) . . ?
C11 C12 C15 112.0(5) . . ?
C11 C12A C15A 110.5(15) . . ?
C17 C13 C11 109.9(6) . . ?
C11 C13A C17A 110.6(16) . . ?
C11 C14 C19 111.5(7) . . ?
C19A C14A C11 107.1(15) . . ?
C16 C15 C12 109.5(8) . . ?
C20 C15 C12 108.1(7) . . ?
C20 C15 C16 108.5(7) . . ?
C12A C15A C16A 110(2) . . ?
C12A C15A C20A 106(2) . . ?
C20A C15A C16A 107(2) . . ?
C17 C16 C15 110.2(8) . . ?
C17A C16A C15A 110(2) . . ?
C16 C17 C13 110.3(7) . . ?
C16 C17 C18 110.0(8) . . ?
C18 C17 C13 109.6(8) . . ?
C13A C17A C16A 108.1(19) . . ?
C18A C17A C13A 110(2) . . ?
C18A C17A C16A 108(2) . . ?
C17 C18 C19 109.7(7) . . ?
C19A C18A C17A 112(2) . . ?
C18 C19 C14 108.4(9) . . ?
C20 C19 C14 108.4(7) . . ?
C20 C19 C18 109.4(9) . . ?
C18A C19A C14A 112(2) . . ?
C18A C19A C20A 110(2) . . ?
C20A C19A C14A 107(2) . . ?
C15 C20 C19 111.2(8) . . ?
C19A C20A C15A 111(2) . . ?
C106 C101 C102 120.0(6) . . ?
C101 C102 C103 118.9(6) . . ?
C104 C103 C102 120.2(6) . . ?
C105 C104 C103 119.7(6) . . ?
C104 C105 C106 120.4(6) . . ?
C101 C106 C105 120.7(6) . . ?

_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 1.716
_oxdiff_exptl_absorpt_empirical_full_min 0.754
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: pyridine/benzene'
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2421902'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2023-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 N, Cl, H2 O'
_chemical_formula_sum            'C21 H26 Cl N O'
_chemical_formula_weight         343.88
_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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        Pccn
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   42.2883(16)
_cell_length_b                   9.4126(2)
_cell_length_c                   9.1436(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3639.54(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4476
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      70.1130
_cell_measurement_theta_min      2.0930
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    1.895
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.912
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
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    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
4 -6 0 0.0035
-4 6 0 0.0115
-2 0 6 0.0380
-27 0 0 0.0043
27 0 0 0.0013
-4 4 4 0.0299
3 -1 -6 0.0348

_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.006
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
4.1195 -6.0320 0.3451 0.5808 -0.0170 -0.8139
-4.1195 6.0320 -0.3451 -0.5808 0.0170 0.8139
-2.3815 0.3709 5.9025 0.8051 -0.0184 0.5929
-27.4324 0.0076 0.1357 -0.0241 -0.9820 0.1872
27.4324 -0.0076 -0.1357 0.0241 0.9820 -0.1872
-3.9606 3.9947 4.0030 0.2165 0.0077 0.9250
2.9654 -0.9972 -6.0013 -0.7637 0.0210 -0.6904

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1118
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -52
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            33635
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.485
_diffrn_reflns_theta_min         4.182
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -27.00   0.50    3.00    --  -51.51 -77.00 150.00  184
  2  ω    -25.00  29.00   0.50    3.00    --   51.89 -19.00-180.00  108
  3  ω    -25.00  52.00   0.50    3.00    --   51.89 -38.00 120.00  154
  4  ω     19.00 104.00   0.50    3.00    --   51.89-125.00 120.00  170
  5  ω    -25.00  29.00   0.50    3.00    --   51.89 -19.00  60.00  108
  6  ω     38.00 130.00   0.50    3.00    --   62.00  76.00-142.76  184
  7  ω   -148.00 -58.00   0.50    3.00    --  -78.00 -69.00 -12.53  180
  8  ω   -112.00 -17.00   0.50   12.00    --  -87.58 125.00-120.00  190
  9  ω   -112.00 -20.00   0.50   12.00    --  -87.58  77.00 120.00  184
 10  ω   -171.00 -79.00   0.50   12.00    --  -95.50 -51.00-130.58  184
 11  ω     35.00 127.00   0.50   12.00    --  102.12 -77.00 150.00  184
 12  ω     88.00 176.00   0.50   12.00    --  102.12  38.00 150.00  176
 13  ω     25.00  52.00   0.50   12.00    --  102.12 -38.00 -30.00   54
 14  ω     63.00 176.00   0.50   12.00    --  102.12  19.00  30.00  226
 15  ω     32.00 111.00   0.50   12.00    --  102.12-125.00-120.00  158
 16  ω     35.00 106.00   0.50   12.00    --  102.12 -99.00 -60.00  142
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015594000
_diffrn_orient_matrix_UB_12      -0.0870603000
_diffrn_orient_matrix_UB_13      0.1424957000
_diffrn_orient_matrix_UB_21      0.0358531000
_diffrn_orient_matrix_UB_22      0.0278497000
_diffrn_orient_matrix_UB_23      0.0095939000
_diffrn_orient_matrix_UB_31      -0.0063453000
_diffrn_orient_matrix_UB_32      0.1357110000
_diffrn_orient_matrix_UB_33      0.0893604000
_diffrn_oxdiff_digest_frames     
;
01425afd63b0c0aba4868b9c88a6b7b25705272030d
;
_diffrn_oxdiff_digest_hkl        
;
010abdc9aaec3a8757b954b9521b4887422ad7
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2431
_reflns_number_total             3688
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         3688
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.010
_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)+(0.0583P)²+2.5377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1343
_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 O(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C17(H17), C19(H19), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C18(H18A,H18B), C20(H20A,
 H20B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.45205(2) 0.61740(7) 0.62921(8) 0.0388(2) Uani 1 1 d . . . . .
N1 N 0.43758(5) 0.3028(2) 0.9609(2) 0.0222(5) Uani 1 1 d . . . . .
C2 C 0.46316(6) 0.2234(3) 0.9968(3) 0.0274(6) Uani 1 1 d . . . . .
H2 H 0.4653 0.1299 0.9588 0.033 Uiso 1 1 calc R . . . .
C3 C 0.48596(7) 0.2772(3) 1.0876(3) 0.0315(6) Uani 1 1 d . . . . .
H3 H 0.5037 0.2208 1.1136 0.038 Uiso 1 1 calc R . . . .
C4 C 0.48304(7) 0.4141(3) 1.1412(3) 0.0311(6) Uani 1 1 d . . . . .
H4 H 0.4988 0.4522 1.2042 0.037 Uiso 1 1 calc R . . . .
C5 C 0.45710(7) 0.4949(3) 1.1026(3) 0.0290(6) Uani 1 1 d . . . . .
H5 H 0.4549 0.5892 1.1382 0.035 Uiso 1 1 calc R . . . .
C6 C 0.43454(7) 0.4372(3) 1.0118(3) 0.0257(6) Uani 1 1 d . . . . .
H6 H 0.4166 0.4922 0.9845 0.031 Uiso 1 1 calc R . . . .
C7 C 0.41251(6) 0.2429(3) 0.8708(3) 0.0220(5) Uani 1 1 d . . . . .
C8 C 0.40380(6) 0.1018(3) 0.8908(3) 0.0240(5) Uani 1 1 d . . . . .
H8 H 0.4150 0.0431 0.9574 0.029 Uiso 1 1 calc R . . . .
C9 C 0.37858(6) 0.0482(3) 0.8124(3) 0.0246(6) Uani 1 1 d . . . . .
H9 H 0.3728 -0.0485 0.8253 0.030 Uiso 1 1 calc R . . . .
C10 C 0.36125(6) 0.1323(3) 0.7141(3) 0.0216(5) Uani 1 1 d . . . . .
C11 C 0.37126(6) 0.2724(3) 0.6944(3) 0.0223(5) Uani 1 1 d . . . . .
H11 H 0.3603 0.3314 0.6271 0.027 Uiso 1 1 calc R . . . .
C12 C 0.39696(6) 0.3280(3) 0.7710(3) 0.0229(5) Uani 1 1 d . . . . .
H12 H 0.4037 0.4230 0.7547 0.027 Uiso 1 1 calc R . . . .
C13 C 0.33325(6) 0.0680(2) 0.6319(3) 0.0211(5) Uani 1 1 d . . . . .
C14 C 0.30965(6) -0.0020(3) 0.7390(3) 0.0260(6) Uani 1 1 d . . . . .
H14A H 0.3209 -0.0731 0.7997 0.031 Uiso 1 1 calc R . . . .
H14B H 0.3008 0.0713 0.8050 0.031 Uiso 1 1 calc R . . . .
C15 C 0.34603(6) -0.0480(3) 0.5278(3) 0.0253(6) Uani 1 1 d . . . . .
H15A H 0.3610 -0.0047 0.4575 0.030 Uiso 1 1 calc R . . . .
H15B H 0.3577 -0.1203 0.5852 0.030 Uiso 1 1 calc R . . . .
C16 C 0.31511(6) 0.1780(3) 0.5397(3) 0.0246(6) Uani 1 1 d . . . . .
H16A H 0.3065 0.2530 0.6044 0.030 Uiso 1 1 calc R . . . .
H16B H 0.3297 0.2234 0.4693 0.030 Uiso 1 1 calc R . . . .
C17 C 0.28277(7) -0.0746(3) 0.6551(3) 0.0288(6) Uani 1 1 d . . . . .
H17 H 0.2679 -0.1198 0.7260 0.035 Uiso 1 1 calc R . . . .
C18 C 0.29631(7) -0.1883(3) 0.5533(3) 0.0312(6) Uani 1 1 d . . . . .
H18A H 0.2789 -0.2357 0.4998 0.037 Uiso 1 1 calc R . . . .
H18B H 0.3076 -0.2611 0.6114 0.037 Uiso 1 1 calc R . . . .
C19 C 0.31912(6) -0.1196(3) 0.4443(3) 0.0271(6) Uani 1 1 d . . . . .
H19 H 0.3279 -0.1939 0.3777 0.033 Uiso 1 1 calc R . . . .
C20 C 0.30140(7) -0.0074(3) 0.3540(3) 0.0300(6) Uani 1 1 d . . . . .
H20A H 0.3160 0.0371 0.2830 0.036 Uiso 1 1 calc R . . . .
H20B H 0.2840 -0.0530 0.2987 0.036 Uiso 1 1 calc R . . . .
C21 C 0.28789(6) 0.1063(3) 0.4562(3) 0.0282(6) Uani 1 1 d . . . . .
H21 H 0.2764 0.1791 0.3971 0.034 Uiso 1 1 calc R . . . .
C22 C 0.26496(7) 0.0372(3) 0.5643(3) 0.0322(7) Uani 1 1 d . . . . .
H22A H 0.2474 -0.0085 0.5104 0.039 Uiso 1 1 calc R . . . .
H22B H 0.2559 0.1105 0.6298 0.039 Uiso 1 1 calc R . . . .
O101 O 0.40724(6) 0.7274(2) 0.8885(3) 0.0454(6) Uani 1 1 d . . . . .
H10A H 0.4221(10) 0.711(4) 0.808(5) 0.068 Uiso 1 1 d R . . . .
H10B H 0.4213(10) 0.770(4) 0.955(5) 0.068 Uiso 1 1 d R . . . .


_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
N1 C2 1.356(3) . ?
N1 C6 1.354(3) . ?
N1 C7 1.456(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.384(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.390(3) . ?
C7 C12 1.381(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.404(4) . ?
C10 C11 1.397(3) . ?
C10 C13 1.528(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.395(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.545(3) . ?
C13 C15 1.546(3) . ?
C13 C16 1.540(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C17 1.532(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C19 1.527(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C21 1.538(4) . ?
C17 H17 1.0000 . ?
C17 C18 1.530(4) . ?
C17 C22 1.537(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.530(4) . ?
C19 H19 1.0000 . ?
C19 C20 1.536(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.531(4) . ?
C21 H21 1.0000 . ?
C21 C22 1.530(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O101 H10A 0.98(4) . ?
O101 H10B 0.94(4) . ?

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 N1 C7 120.3(2) . . ?
C6 N1 C2 120.5(2) . . ?
C6 N1 C7 119.1(2) . . ?
N1 C2 H2 119.8 . . ?
N1 C2 C3 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 120.4 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
N1 C6 C5 120.7(3) . . ?
N1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 N1 119.3(2) . . ?
C12 C7 N1 119.7(2) . . ?
C12 C7 C8 121.0(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 121.9(2) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C13 119.7(2) . . ?
C11 C10 C9 117.2(2) . . ?
C11 C10 C13 123.1(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C11 119.1(2) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C10 C13 C14 110.9(2) . . ?
C10 C13 C15 108.2(2) . . ?
C10 C13 C16 112.9(2) . . ?
C14 C13 C15 108.4(2) . . ?
C16 C13 C14 108.2(2) . . ?
C16 C13 C15 108.2(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C17 C14 C13 110.6(2) . . ?
C17 C14 H14A 109.5 . . ?
C17 C14 H14B 109.5 . . ?
C13 C15 H15A 109.4 . . ?
C13 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C19 C15 C13 111.0(2) . . ?
C19 C15 H15A 109.4 . . ?
C19 C15 H15B 109.4 . . ?
C13 C16 H16A 109.6 . . ?
C13 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
C21 C16 C13 110.4(2) . . ?
C21 C16 H16A 109.6 . . ?
C21 C16 H16B 109.6 . . ?
C14 C17 H17 109.4 . . ?
C14 C17 C22 109.2(2) . . ?
C18 C17 C14 109.8(2) . . ?
C18 C17 H17 109.4 . . ?
C18 C17 C22 109.5(2) . . ?
C22 C17 H17 109.4 . . ?
C17 C18 H18A 109.7 . . ?
C17 C18 H18B 109.7 . . ?
C17 C18 C19 109.6(2) . . ?
H18A C18 H18B 108.2 . . ?
C19 C18 H18A 109.7 . . ?
C19 C18 H18B 109.7 . . ?
C15 C19 C18 109.3(2) . . ?
C15 C19 H19 109.6 . . ?
C15 C19 C20 109.2(2) . . ?
C18 C19 H19 109.6 . . ?
C18 C19 C20 109.5(2) . . ?
C20 C19 H19 109.6 . . ?
C19 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.2 . . ?
C21 C20 C19 109.5(2) . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C16 C21 H21 109.4 . . ?
C20 C21 C16 109.3(2) . . ?
C20 C21 H21 109.4 . . ?
C22 C21 C16 109.9(2) . . ?
C22 C21 C20 109.5(2) . . ?
C22 C21 H21 109.4 . . ?
C17 C22 H22A 109.8 . . ?
C17 C22 H22B 109.8 . . ?
C21 C22 C17 109.2(2) . . ?
C21 C22 H22A 109.8 . . ?
C21 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
H10A O101 H10B 99(3) . . ?

_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 1.198
_oxdiff_exptl_absorpt_empirical_full_min 0.820
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol/benzene'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2421903'
loop_
_audit_author_name
_audit_author_address
'Jas Ward'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2025-02-06 deposited with the CCDC.	2025-04-10 downloaded from the CCDC.
;
_audit_creation_date             2023-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 N, C2 H6 O, I'
_chemical_formula_sum            'C24 H32 I N O'
_chemical_formula_weight         477.40
_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'
I I -0.3257 6.8362 '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           61
_space_group_name_H-M_alt        Pbca
_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'
'-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                   12.4980(3)
_cell_length_b                   11.2458(2)
_cell_length_c                   31.4625(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4422.06(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12481
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.4180
_cell_measurement_theta_min      2.8080
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    11.462
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.114
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -5 0 0.0500
6 5 0 0.0440
-6 5 -1 0.1061
6 -5 1 0.1031
0 0 -20 0.0010
0 0 20 0.0097

_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.011
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
-5.6901 -5.1971 -0.4519 0.4976 0.0371 0.8666
5.6901 5.1971 0.4519 -0.4976 -0.0371 -0.8666
-5.5639 5.2933 -1.3146 0.8461 0.0691 -0.5285
5.5639 -5.2933 1.3146 -0.8461 -0.0691 0.5285
-0.3040 0.0585 -20.4141 0.0251 0.9996 -0.0091
0.3040 -0.0585 20.4141 -0.0251 -0.9996 0.0091

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            32744
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.499
_diffrn_reflns_theta_min         2.809
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -119.00 -78.00   0.50    0.05    --  -51.51-145.00-115.00   82
  2  ω     -2.00  24.00   0.50    0.05    --  -51.51  19.00  69.00   52
  3  ω   -154.00-101.00   0.50    0.15    --  -87.61-107.00 132.00  106
  4  ω     66.00 153.00   0.50    0.15    --  102.08  19.00  69.00  174
  5  ω     33.00 106.00   0.50    0.15    --  102.08-107.00 132.00  146
  6  ω     47.00  72.00   0.50    0.15    --  102.08-126.00  52.00   50
  7  ω   -118.00 -41.00   0.50    0.05    --  -51.51 -77.00-180.00  154
  8  ω     -4.00  21.00   0.50    0.05    --  -51.51  19.00 150.00   50
  9  ω    -76.00  14.00   0.50    0.05    --  -51.51  77.00 120.00  180
 10  ω    -47.00 -21.00   0.50    0.15    --  -87.61  57.00   0.00   52
 11  ω    -44.00 -14.00   0.50    0.15    --  -87.61  57.00-120.00   60
 12  ω     38.00  64.00   0.50    0.15    --  102.08 -57.00 -30.00   52
 13  ω     36.00  73.00   0.50    0.15    --  102.08 -57.00 120.00   74
 14  ω     71.00 127.00   0.50    0.15    --  102.08 -77.00 120.00  112
 15  ω     38.00  68.00   0.50    0.15    --  102.08 -57.00  30.00   60
 16  ω     41.00  67.00   0.50    0.15    --  102.08 -77.00 120.00   52
 17  ω     28.00  74.00   0.50    0.15    --  102.08 -57.00-180.00   92
 18  ω     25.00  52.00   0.50    0.15    --  102.08 -38.00 -90.00   54
 19  ω     39.00  78.00   0.50    0.15    --  102.08 -57.00 -60.00   78
 20  ω     43.00  71.00   0.50    0.15    --  102.08 -57.00   0.00   56
 21  ω     26.00  52.00   0.50    0.15    --  102.08 -38.00 120.00   52
 22  ω     39.00  75.00   0.50    0.15    --  102.08 -57.00 150.00   72
 23  ω     93.00 162.00   0.50    0.15    --  102.08 125.00-150.00  138
 24  ω     26.00  51.00   0.50    0.15    --  102.08 -38.00  30.00   50
 25  ω     25.00  52.00   0.50    0.15    --  102.08 -38.00  90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix-Arc 100'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1192055000
_diffrn_orient_matrix_UB_12      0.0347045000
_diffrn_orient_matrix_UB_13      0.0006453000
_diffrn_orient_matrix_UB_21      -0.0017668000
_diffrn_orient_matrix_UB_22      -0.0009572000
_diffrn_orient_matrix_UB_23      -0.0489448000
_diffrn_orient_matrix_UB_31      -0.0312566000
_diffrn_orient_matrix_UB_32      -0.1325707000
_diffrn_orient_matrix_UB_33      0.0005292000
_diffrn_oxdiff_digest_frames     
;
018531e0cd0e6e5a000dda1c913afd550c02102f503
;
_diffrn_oxdiff_digest_hkl        
;
01484905900d26b7b0f3b41019b1c92e20318f
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3921
_reflns_number_total             4505
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.199
_refine_diff_density_min         -1.592
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.209
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4505
_refine_ls_number_restraints     258
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0731
_refine_ls_restrained_S_all      1.176
_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)+66.0290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1536
_refine_ls_wR_factor_ref         0.1569
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C14 \\sim C15 \\sim C15A \\sim C16 \\sim C16A \\sim C17 \\sim C17A \\sim C18
\\sim C18A \\sim C19 \\sim C19A \\sim C20 \\sim C20A \\sim C21 \\sim C21A \\sim
C22 \\sim C22A \\sim C23 \\sim C23A: within 1.7A with sigma of 0.02 and sigma
for terminal atoms of 0.04
3. Others
 Sof(C20A)=Sof(H20A)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=Sof(H16C)=
 Sof(H16D)=Sof(C17A)=Sof(H17C)=Sof(H17D)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19C)=Sof(H19D)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=
 Sof(C23A)=Sof(H23A)=Sof(H23B)=1-FVAR(1)
 Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(H17A)=
 Sof(H17B)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21C)=Sof(H21D)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23C)=Sof(H23D)=
 FVAR(1)
4.a Free rotating group:
 C20A(C15A,C16A,C17A,C18A,C19A,C21A,C22A,C23A)
4.b Ternary CH refined with riding coordinates:
 C18(H18), C20(H20), C20A(H20A), C18A(H18A), C22A(H22A), C22(H22)
4.c Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C19(H19A,H19B), C15A(H15C,
 H15D), C16A(H16C,H16D), C17A(H17C,H17D), C19A(H19C,H19D), C21A(H21A,H21B),
 C23A(H23A,H23B), C21(H21C,H21D), C23(H23C,H23D), C102(H10A,H10B)
4.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13)
4.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C103(H10C,H10D,H10E)
4.f Idealised tetrahedral OH refined as rotating group:
 O101(H101)
;
_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
N1 N 0.7120(6) 0.5132(6) 0.5451(2) 0.0267(15) Uani 1 1 d . . . . .
C2 C 0.7796(7) 0.5859(7) 0.5248(3) 0.0266(17) Uani 1 1 d . . . . .
H2 H 0.8311 0.6295 0.5406 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7757(7) 0.5986(7) 0.4812(3) 0.0283(18) Uani 1 1 d . . . . .
H3 H 0.8242 0.6507 0.4673 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7008(6) 0.5354(6) 0.4576(2) 0.0212(15) Uani 1 1 d . . . . .
C5 C 0.6344(7) 0.4576(7) 0.4794(2) 0.0248(16) Uani 1 1 d . . . . .
H5 H 0.5840 0.4105 0.4643 0.030 Uiso 1 1 calc R . . . .
C6 C 0.6414(7) 0.4485(7) 0.5225(3) 0.0283(18) Uani 1 1 d . . . . .
H6 H 0.5952 0.3951 0.5371 0.034 Uiso 1 1 calc R . . . .
C7 C 0.7144(7) 0.5050(8) 0.5916(2) 0.0302(19) Uani 1 1 d . . . . .
H7A H 0.6885 0.5797 0.6039 0.045 Uiso 1 1 calc GR . . . .
H7B H 0.7880 0.4904 0.6011 0.045 Uiso 1 1 calc GR . . . .
H7C H 0.6684 0.4394 0.6009 0.045 Uiso 1 1 calc GR . . . .
C8 C 0.6907(7) 0.5541(6) 0.4108(2) 0.0242(16) Uani 1 1 d . . . . .
C9 C 0.7607(6) 0.6288(8) 0.3884(3) 0.0283(17) Uani 1 1 d . . . . .
H9 H 0.8186 0.6658 0.4029 0.034 Uiso 1 1 calc R . . . .
C10 C 0.7457(6) 0.6490(7) 0.3454(3) 0.0279(18) Uani 1 1 d . . . . .
H10 H 0.7947 0.6992 0.3308 0.034 Uiso 1 1 calc R . . . .
C11 C 0.6611(6) 0.5983(6) 0.3224(2) 0.0227(16) Uani 1 1 d . . . . .
C12 C 0.5946(8) 0.5214(7) 0.3448(3) 0.033(2) Uani 1 1 d . . . . .
H12 H 0.5381 0.4823 0.3302 0.039 Uiso 1 1 calc R . . . .
C13 C 0.6084(8) 0.5002(7) 0.3879(3) 0.0319(19) Uani 1 1 d . . . . .
H13 H 0.5608 0.4478 0.4021 0.038 Uiso 1 1 calc R . . . .
C14 C 0.6437(6) 0.6253(6) 0.2755(2) 0.0184(14) Uani 1 1 d . U . . .
C15 C 0.6426(11) 0.7588(10) 0.2667(4) 0.018(2) Uani 0.562(8) 1 d . U P A 1
H15A H 0.7099 0.7945 0.2773 0.022 Uiso 0.562(8) 1 calc R . P A 1
H15B H 0.5824 0.7958 0.2822 0.022 Uiso 0.562(8) 1 calc R . P A 1
C16 C 0.5313(10) 0.5754(12) 0.2574(4) 0.022(3) Uani 0.562(8) 1 d . U P A 1
H16A H 0.5275 0.4882 0.2616 0.027 Uiso 0.562(8) 1 calc R . P A 1
H16B H 0.4712 0.6123 0.2731 0.027 Uiso 0.562(8) 1 calc R . P A 1
C17 C 0.7307(11) 0.5647(11) 0.2488(4) 0.020(3) Uani 0.562(8) 1 d . U P A 1
H17A H 0.7275 0.4777 0.2535 0.024 Uiso 0.562(8) 1 calc R . P A 1
H17B H 0.8018 0.5929 0.2583 0.024 Uiso 0.562(8) 1 calc R . P A 1
C18 C 0.6309(12) 0.7859(13) 0.2180(5) 0.021(3) Uani 0.562(8) 1 d . U P A 1
H18 H 0.6343 0.8738 0.2133 0.025 Uiso 0.562(8) 1 calc R . P A 1
C19 C 0.5247(11) 0.7395(12) 0.2026(5) 0.022(3) Uani 0.562(8) 1 d . U P A 1
H19A H 0.5155 0.7578 0.1721 0.026 Uiso 0.562(8) 1 calc R . P A 1
H19B H 0.4658 0.7780 0.2186 0.026 Uiso 0.562(8) 1 calc R . P A 1
C20 C 0.5215(13) 0.6044(14) 0.2096(6) 0.019(3) Uani 0.562(8) 1 d . U P A 1
H20 H 0.4516 0.5731 0.1989 0.023 Uiso 0.562(8) 1 calc R . P A 1
C20A C 0.6367(7) 0.5404(7) 0.2026(3) 0.020(3) Uani 0.438(8) 1 d . U P A 2
H20A H 0.6433 0.4656 0.1857 0.024 Uiso 0.438(8) 1 calc R . P A 2
C15A C 0.5338(7) 0.6803(9) 0.2714(3) 0.018(3) Uani 0.438(8) 1 d G U P A 2
H15C H 0.5303 0.7547 0.2882 0.021 Uiso 0.438(8) 1 calc R . P A 2
H15D H 0.4790 0.6249 0.2825 0.021 Uiso 0.438(8) 1 calc R . P A 2
C16A C 0.6587(8) 0.5136(6) 0.2501(3) 0.016(3) Uani 0.438(8) 1 d G U P A 2
H16C H 0.6089 0.4514 0.2604 0.019 Uiso 0.438(8) 1 calc R . P A 2
H16D H 0.7328 0.4840 0.2537 0.019 Uiso 0.438(8) 1 calc R . P A 2
C17A C 0.7306(6) 0.7221(8) 0.2601(3) 0.014(3) Uani 0.438(8) 1 d G U P A 2
H17C H 0.7241 0.7956 0.2772 0.017 Uiso 0.438(8) 1 calc R . P A 2
H17D H 0.8039 0.6902 0.2637 0.017 Uiso 0.438(8) 1 calc R . P A 2
C18A C 0.5115(5) 0.7075(8) 0.2239(3) 0.018(3) Uani 0.438(8) 1 d G U P A 2
H18A H 0.4375 0.7402 0.2208 0.022 Uiso 0.438(8) 1 calc R . P A 2
C19A C 0.5220(7) 0.5914(9) 0.1977(3) 0.020(4) Uani 0.438(8) 1 d G U P A 2
H19C H 0.5072 0.6081 0.1674 0.024 Uiso 0.438(8) 1 calc R . P A 2
H19D H 0.4691 0.5323 0.2079 0.024 Uiso 0.438(8) 1 calc R . P A 2
C21A C 0.7189(7) 0.6331(9) 0.1863(3) 0.021(3) Uani 0.438(8) 1 d G U P A 2
H21A H 0.7922 0.6008 0.1891 0.025 Uiso 0.438(8) 1 calc R . P A 2
H21B H 0.7055 0.6501 0.1559 0.025 Uiso 0.438(8) 1 calc R . P A 2
C22A C 0.7087(7) 0.7493(7) 0.2125(3) 0.018(3) Uani 0.438(8) 1 d G U P A 2
H22A H 0.7618 0.8090 0.2020 0.022 Uiso 0.438(8) 1 calc R . P A 2
C23A C 0.5939(8) 0.7998(7) 0.2076(3) 0.021(4) Uani 0.438(8) 1 d G U P A 2
H23A H 0.5872 0.8744 0.2241 0.025 Uiso 0.438(8) 1 calc R . P A 2
H23B H 0.5797 0.8181 0.1774 0.025 Uiso 0.438(8) 1 calc R . P A 2
C21 C 0.6097(12) 0.5461(13) 0.1856(5) 0.024(3) Uani 0.562(8) 1 d . U P A 1
H21C H 0.6017 0.5632 0.1549 0.029 Uiso 0.562(8) 1 calc R . P A 1
H21D H 0.6056 0.4589 0.1896 0.029 Uiso 0.562(8) 1 calc R . P A 1
C22 C 0.7176(12) 0.5908(13) 0.2009(5) 0.021(3) Uani 0.562(8) 1 d . U P A 1
H22 H 0.7764 0.5517 0.1845 0.025 Uiso 0.562(8) 1 calc R . P A 1
C23 C 0.7214(12) 0.7267(13) 0.1944(5) 0.025(3) Uani 0.562(8) 1 d . U P A 1
H23C H 0.7906 0.7580 0.2048 0.030 Uiso 0.562(8) 1 calc R . P A 1
H23D H 0.7157 0.7451 0.1637 0.030 Uiso 0.562(8) 1 calc R . P A 1
O101 O 0.4964(5) 0.2303(5) 0.54329(19) 0.0328(13) Uani 1 1 d . . . . .
H101 H 0.4860 0.2189 0.5172 0.049 Uiso 1 1 calc GR . . . .
C102 C 0.4343(8) 0.1487(7) 0.5672(3) 0.037(2) Uani 1 1 d . . . . .
H10A H 0.4443 0.0670 0.5561 0.044 Uiso 1 1 calc R . . . .
H10B H 0.3575 0.1693 0.5651 0.044 Uiso 1 1 calc R . . . .
C103 C 0.4710(9) 0.1558(9) 0.6125(3) 0.045(3) Uani 1 1 d . . . . .
H10C H 0.5473 0.1361 0.6141 0.067 Uiso 1 1 calc GR . . . .
H10D H 0.4301 0.0993 0.6298 0.067 Uiso 1 1 calc GR . . . .
H10E H 0.4596 0.2366 0.6233 0.067 Uiso 1 1 calc GR . . . .
I1 I 0.43847(4) 0.20812(4) 0.43468(2) 0.02585(16) 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
N1 C2 1.339(10) . ?
N1 C6 1.345(10) . ?
N1 C7 1.467(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.379(12) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(11) . ?
C4 C5 1.388(11) . ?
C4 C8 1.494(10) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(11) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.401(11) . ?
C8 C13 1.394(12) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.402(11) . ?
C11 C12 1.392(11) . ?
C11 C14 1.521(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.388(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.527(14) . ?
C14 C16 1.617(14) . ?
C14 C17 1.534(14) . ?
C14 C15A 1.512(11) . ?
C14 C16A 1.500(11) . ?
C14 C17A 1.613(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C18 1.568(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C20 1.54(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C22 1.544(19) . ?
C18 H18 1.0000 . ?
C18 C19 1.507(18) . ?
C18 C23 1.51(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.54(2) . ?
C20 H20 1.0000 . ?
C20 C21 1.49(2) . ?
C20A H20A 1.0000 . ?
C20A C16A 1.5500 . ?
C20A C19A 1.5508 . ?
C20A C21A 1.5507 . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C18A 1.5496 . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C17A C22A 1.5516 . ?
C18A H18A 1.0000 . ?
C18A C19A 1.5496 . ?
C18A C23A 1.5501 . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C21A H21A 0.9900 . ?
C21A H21B 0.9900 . ?
C21A C22A 1.5504 . ?
C22A H22A 1.0000 . ?
C22A C23A 1.5501 . ?
C23A H23A 0.9900 . ?
C23A H23B 0.9900 . ?
C21 H21C 0.9900 . ?
C21 H21D 0.9900 . ?
C21 C22 1.52(2) . ?
C22 H22 1.0000 . ?
C22 C23 1.543(19) . ?
C23 H23C 0.9900 . ?
C23 H23D 0.9900 . ?
O101 H101 0.8400 . ?
O101 C102 1.417(10) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C102 C103 1.501(13) . ?
C103 H10C 0.9800 . ?
C103 H10D 0.9800 . ?
C103 H10E 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
C2 N1 C6 119.5(7) . . ?
C2 N1 C7 120.1(7) . . ?
C6 N1 C7 120.4(7) . . ?
N1 C2 H2 119.5 . . ?
N1 C2 C3 121.0(8) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(8) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C8 120.7(7) . . ?
C5 C4 C3 117.5(7) . . ?
C5 C4 C8 121.8(7) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
N1 C6 C5 121.8(8) . . ?
N1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C4 121.8(7) . . ?
C13 C8 C4 120.6(7) . . ?
C13 C8 C9 117.6(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(8) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 118.7 . . ?
C9 C10 C11 122.6(7) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C14 121.8(7) . . ?
C12 C11 C10 116.2(7) . . ?
C12 C11 C14 122.0(7) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(8) . . ?
C13 C12 H12 119.1 . . ?
C8 C13 H13 119.3 . . ?
C12 C13 C8 121.4(8) . . ?
C12 C13 H13 119.3 . . ?
C11 C14 C15 111.9(7) . . ?
C11 C14 C16 113.4(7) . . ?
C11 C14 C17 109.9(7) . . ?
C11 C14 C17A 109.2(6) . . ?
C15 C14 C16 105.6(8) . . ?
C15 C14 C17 110.1(8) . . ?
C17 C14 C16 105.6(8) . . ?
C15A C14 C11 107.1(6) . . ?
C15A C14 C17A 108.1(6) . . ?
C16A C14 C11 109.3(6) . . ?
C16A C14 C15A 114.3(7) . . ?
C16A C14 C17A 108.7(6) . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C14 C15 C18 111.7(10) . . ?
H15A C15 H15B 107.9 . . ?
C18 C15 H15A 109.3 . . ?
C18 C15 H15B 109.3 . . ?
C14 C16 H16A 109.7 . . ?
C14 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C20 C16 C14 109.8(10) . . ?
C20 C16 H16A 109.7 . . ?
C20 C16 H16B 109.7 . . ?
C14 C17 H17A 109.2 . . ?
C14 C17 H17B 109.2 . . ?
C14 C17 C22 112.1(10) . . ?
H17A C17 H17B 107.9 . . ?
C22 C17 H17A 109.2 . . ?
C22 C17 H17B 109.2 . . ?
C15 C18 H18 109.4 . . ?
C19 C18 C15 109.2(12) . . ?
C19 C18 H18 109.4 . . ?
C19 C18 C23 110.5(13) . . ?
C23 C18 C15 109.0(12) . . ?
C23 C18 H18 109.4 . . ?
C18 C19 H19A 110.0 . . ?
C18 C19 H19B 110.0 . . ?
C18 C19 C20 108.7(12) . . ?
H19A C19 H19B 108.3 . . ?
C20 C19 H19A 110.0 . . ?
C20 C19 H19B 110.0 . . ?
C16 C20 H20 108.8 . . ?
C19 C20 C16 110.2(13) . . ?
C19 C20 H20 108.8 . . ?
C21 C20 C16 110.0(13) . . ?
C21 C20 C19 110.1(13) . . ?
C21 C20 H20 108.8 . . ?
C16A C20A H20A 109.6 . . ?
C16A C20A C19A 109.4 . . ?
C16A C20A C21A 109.4 . . ?
C19A C20A H20A 109.6 . . ?
C21A C20A H20A 109.6 . . ?
C21A C20A C19A 109.3 . . ?
C14 C15A H15C 109.9 . . ?
C14 C15A H15D 109.9 . . ?
C14 C15A C18A 109.0(4) . . ?
H15C C15A H15D 108.3 . . ?
C18A C15A H15C 109.9 . . ?
C18A C15A H15D 109.9 . . ?
C14 C16A C20A 109.1(4) . . ?
C14 C16A H16C 109.9 . . ?
C14 C16A H16D 109.9 . . ?
C20A C16A H16C 109.9 . . ?
C20A C16A H16D 109.9 . . ?
H16C C16A H16D 108.3 . . ?
C14 C17A H17C 110.2 . . ?
C14 C17A H17D 110.2 . . ?
H17C C17A H17D 108.5 . . ?
C22A C17A C14 107.7(4) . . ?
C22A C17A H17C 110.2 . . ?
C22A C17A H17D 110.2 . . ?
C15A C18A H18A 109.6 . . ?
C15A C18A C19A 109.4 . . ?
C15A C18A C23A 109.4 . . ?
C19A C18A H18A 109.6 . . ?
C19A C18A C23A 109.4 . . ?
C23A C18A H18A 109.6 . . ?
C20A C19A H19C 109.7 . . ?
C20A C19A H19D 109.7 . . ?
C18A C19A C20A 109.7 . . ?
C18A C19A H19C 109.7 . . ?
C18A C19A H19D 109.7 . . ?
H19C C19A H19D 108.2 . . ?
C20A C21A H21A 109.7 . . ?
C20A C21A H21B 109.7 . . ?
H21A C21A H21B 108.2 . . ?
C22A C21A C20A 109.6 . . ?
C22A C21A H21A 109.7 . . ?
C22A C21A H21B 109.7 . . ?
C17A C22A H22A 109.6 . . ?
C21A C22A C17A 109.4 . . ?
C21A C22A H22A 109.6 . . ?
C23A C22A C17A 109.4 . . ?
C23A C22A C21A 109.4 . . ?
C23A C22A H22A 109.6 . . ?
C18A C23A C22A 109.7 . . ?
C18A C23A H23A 109.7 . . ?
C18A C23A H23B 109.7 . . ?
C22A C23A H23A 109.7 . . ?
C22A C23A H23B 109.7 . . ?
H23A C23A H23B 108.2 . . ?
C20 C21 H21C 109.5 . . ?
C20 C21 H21D 109.5 . . ?
C20 C21 C22 110.7(13) . . ?
H21C C21 H21D 108.1 . . ?
C22 C21 H21C 109.5 . . ?
C22 C21 H21D 109.5 . . ?
C17 C22 H22 110.1 . . ?
C21 C22 C17 109.9(12) . . ?
C21 C22 H22 110.1 . . ?
C21 C22 C23 108.2(12) . . ?
C23 C22 C17 108.4(12) . . ?
C23 C22 H22 110.1 . . ?
C18 C23 C22 110.4(12) . . ?
C18 C23 H23C 109.6 . . ?
C18 C23 H23D 109.6 . . ?
C22 C23 H23C 109.6 . . ?
C22 C23 H23D 109.6 . . ?
H23C C23 H23D 108.1 . . ?
C102 O101 H101 109.5 . . ?
O101 C102 H10A 110.2 . . ?
O101 C102 H10B 110.2 . . ?
O101 C102 C103 107.6(8) . . ?
H10A C102 H10B 108.5 . . ?
C103 C102 H10A 110.2 . . ?
C103 C102 H10B 110.2 . . ?
C102 C103 H10C 109.5 . . ?
C102 C103 H10D 109.5 . . ?
C102 C103 H10E 109.5 . . ?
H10C C103 H10D 109.5 . . ?
H10C C103 H10E 109.5 . . ?
H10D C103 H10E 109.5 . . ?

_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.860

#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol/pentane'
