# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_knm323a-gpc2-fr1_etoac_pentane_x-ray_auto
_database_code_depnum_ccdc_archive 'CCDC 2506075'
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        5?-Me
_chemical_formula_moiety         'C26 H23 N3 O2'
_chemical_formula_sum            'C26 H23 N3 O2'
_chemical_formula_weight         409.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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                   15.0386(5)
_cell_length_b                   14.8556(6)
_cell_length_c                   18.6742(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4172.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8528
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.9170
_cell_measurement_theta_min      2.2230
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53326
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
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    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.815
_diffrn_reflns_theta_min         2.181
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00 -38.00   0.50   10.00    --    3.32 -42.00 130.00   62
  2  ω      1.00  33.00   0.50   10.00    --    3.32 -99.00  30.00   64
  3  ω    -73.00 -41.00   0.50   10.00    --    3.32 -37.00  30.00   64
  4  ω    -31.00   4.00   0.50   10.00    --    3.32 -37.00  30.00   70
  5  ω    -29.00  18.00   0.50   10.00    --    3.32 -42.00 130.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0339445000
_diffrn_orient_matrix_UB_12      0.0243001000
_diffrn_orient_matrix_UB_13      -0.0179898000
_diffrn_orient_matrix_UB_21      0.0211697000
_diffrn_orient_matrix_UB_22      -0.0410661000
_diffrn_orient_matrix_UB_23      -0.0091946000
_diffrn_orient_matrix_UB_31      -0.0249864000
_diffrn_orient_matrix_UB_32      -0.0017951000
_diffrn_orient_matrix_UB_33      -0.0321587000
_diffrn_oxdiff_digest_frames     
;
0186bf8ded6acc556ed0e7cf9a551bf4830002538d4
;
_diffrn_oxdiff_digest_hkl        
;
0188151e5c02857470486bbb57c2190e8237cf
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4111
_reflns_number_total             4984
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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         0.311
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²+1.8445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H009), C1(H00D)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H00F), C8(H00G), C31(H00H), C27(H00I), C4(H00J), C28(H00K), C3(H00L),
 C6(H00M), C7(H00N), C24(H00O), C21(H00P), C29(H00Q), C30(H00R), C22(H00T),
 C23(H00U)
2.c Idealised Me refined as rotating group:
 C16(H00A,H00B,H00C), C18(H00E,H00S,H00V)
;
_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
O19 O 0.68504(6) 0.47575(7) 0.27394(5) 0.0256(2) Uani 1 1 d . . . . .
O17 O 0.49234(7) 0.44077(7) 0.08623(5) 0.0279(2) Uani 1 1 d . . . . .
N11 N 0.53224(7) 0.49550(7) 0.26293(5) 0.0153(2) Uani 1 1 d . . . . .
N12 N 0.47518(7) 0.49559(8) 0.20198(5) 0.0166(2) Uani 1 1 d . . . . .
N14 N 0.60884(8) 0.45243(8) 0.16754(6) 0.0218(3) Uani 1 1 d . . . . .
C10 C 0.46415(8) 0.55661(9) 0.37515(6) 0.0159(3) Uani 1 1 d . . . . .
C26 C 0.43321(8) 0.70219(9) 0.12496(6) 0.0162(3) Uani 1 1 d . . . . .
C5 C 0.44131(8) 0.63201(9) 0.41704(6) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.50175(8) 0.66126(9) 0.27238(6) 0.0152(2) Uani 1 1 d . . . . .
H009 H 0.440201 0.654425 0.252858 0.018 Uiso 1 1 calc R . . . .
C13 C 0.52165(9) 0.46091(9) 0.14456(7) 0.0194(3) Uani 1 1 d . . . . .
C25 C 0.53035(8) 0.69434(9) 0.13998(6) 0.0168(3) Uani 1 1 d . . . . .
C20 C 0.56364(8) 0.68036(8) 0.20963(6) 0.0157(2) Uani 1 1 d . . . . .
C1 C 0.52567(8) 0.57329(9) 0.31186(6) 0.0152(2) Uani 1 1 d . . . . .
H00D H 0.586462 0.582399 0.332327 0.018 Uiso 1 1 calc R . . . .
C15 C 0.61755(8) 0.47495(9) 0.23851(7) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.43919(8) 0.47114(9) 0.39739(7) 0.0190(3) Uani 1 1 d . . . . .
H00F H 0.454982 0.420106 0.369497 0.023 Uiso 1 1 calc R . . . .
C8 C 0.39103(9) 0.45992(10) 0.46056(7) 0.0222(3) Uani 1 1 d . . . . .
H00G H 0.373590 0.401283 0.475213 0.027 Uiso 1 1 calc R . . . .
C31 C 0.39130(9) 0.64417(9) 0.07680(7) 0.0203(3) Uani 1 1 d . . . . .
H00H H 0.424588 0.598559 0.053298 0.024 Uiso 1 1 calc R . . . .
C27 C 0.38303(9) 0.76989(9) 0.15742(7) 0.0195(3) Uani 1 1 d . . . . .
H00I H 0.410913 0.810035 0.190031 0.023 Uiso 1 1 calc R . . . .
C4 C 0.47051(9) 0.72157(9) 0.39390(7) 0.0201(3) Uani 1 1 d . . . . .
H00J H 0.468560 0.770233 0.426866 0.024 Uiso 1 1 calc R . . . .
C28 C 0.29291(9) 0.77950(10) 0.14278(7) 0.0233(3) Uani 1 1 d . . . . .
H00K H 0.259786 0.826349 0.164858 0.028 Uiso 1 1 calc R . . . .
C3 C 0.49979(9) 0.73606(9) 0.32743(7) 0.0197(3) Uani 1 1 d . . . . .
H00L H 0.519789 0.794461 0.314389 0.024 Uiso 1 1 calc R . . . .
C6 C 0.39365(9) 0.61950(10) 0.48047(7) 0.0217(3) Uani 1 1 d . . . . .
H00M H 0.378370 0.670100 0.509042 0.026 Uiso 1 1 calc R . . . .
C7 C 0.36840(9) 0.53384(11) 0.50215(7) 0.0235(3) Uani 1 1 d . . . . .
H00N H 0.335794 0.525881 0.545256 0.028 Uiso 1 1 calc R . . . .
C24 C 0.59037(9) 0.70209(10) 0.08311(7) 0.0244(3) Uani 1 1 d . . . . .
H00O H 0.568325 0.709247 0.035774 0.029 Uiso 1 1 calc R . . . .
C21 C 0.65553(9) 0.68007(9) 0.22018(7) 0.0208(3) Uani 1 1 d . . . . .
H00P H 0.678418 0.673093 0.267273 0.025 Uiso 1 1 calc R . . . .
C29 C 0.25144(9) 0.72049(11) 0.09585(7) 0.0252(3) Uani 1 1 d . . . . .
H00Q H 0.189693 0.726175 0.086121 0.030 Uiso 1 1 calc R . . . .
C30 C 0.30085(9) 0.65316(10) 0.06326(7) 0.0250(3) Uani 1 1 d . . . . .
H00R H 0.272484 0.612614 0.031228 0.030 Uiso 1 1 calc R . . . .
C16 C 0.38176(9) 0.47338(10) 0.21282(8) 0.0227(3) Uani 1 1 d . . . . .
H00A H 0.377132 0.416333 0.238906 0.034 Uiso 1 1 calc GR . . . .
H00B H 0.352234 0.467625 0.166262 0.034 Uiso 1 1 calc GR . . . .
H00C H 0.353096 0.521254 0.240582 0.034 Uiso 1 1 calc GR . . . .
C22 C 0.71414(9) 0.68976(10) 0.16329(8) 0.0266(3) Uani 1 1 d . . . . .
H00T H 0.776462 0.689698 0.171601 0.032 Uiso 1 1 calc R . . . .
C23 C 0.68158(10) 0.69950(11) 0.09451(8) 0.0293(3) Uani 1 1 d . . . . .
H00U H 0.721419 0.704406 0.055223 0.035 Uiso 1 1 calc R . . . .
C18 C 0.68295(11) 0.42784(12) 0.12159(9) 0.0365(4) Uani 1 1 d . . . . .
H00E H 0.667551 0.373800 0.094164 0.055 Uiso 1 1 calc GR . . . .
H00S H 0.735520 0.415711 0.151054 0.055 Uiso 1 1 calc GR . . . .
H00V H 0.695741 0.477438 0.088551 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O19 C15 1.2116(16) . ?
O17 C13 1.2126(16) . ?
N11 N12 1.4255(14) . ?
N11 C1 1.4766(16) . ?
N11 C15 1.3954(16) . ?
N12 C13 1.3796(16) . ?
N12 C16 1.4572(16) . ?
N14 C13 1.3855(18) . ?
N14 C15 1.3732(17) . ?
N14 C18 1.4532(17) . ?
C10 C5 1.4088(18) . ?
C10 C1 1.5213(16) . ?
C10 C9 1.3877(19) . ?
C26 C25 1.4920(17) . ?
C26 C31 1.3961(18) . ?
C26 C27 1.3958(18) . ?
C5 C4 1.4662(19) . ?
C5 C6 1.3968(18) . ?
C2 C20 1.5232(16) . ?
C2 C1 1.5430(17) . ?
C2 C3 1.5140(17) . ?
C25 C20 1.4091(17) . ?
C25 C24 1.3986(18) . ?
C20 C21 1.3959(18) . ?
C9 C8 1.3941(18) . ?
C8 C7 1.387(2) . ?
C31 C30 1.3900(19) . ?
C27 C28 1.3899(19) . ?
C4 C3 1.3346(18) . ?
C28 C29 1.388(2) . ?
C6 C7 1.388(2) . ?
C24 C23 1.389(2) . ?
C21 C22 1.3879(19) . ?
C29 C30 1.387(2) . ?
C22 C23 1.382(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N12 N11 C1 116.95(9) . . ?
C15 N11 N12 107.02(10) . . ?
C15 N11 C1 115.78(10) . . ?
N11 N12 C16 117.98(10) . . ?
C13 N12 N11 108.38(10) . . ?
C13 N12 C16 120.78(11) . . ?
C13 N14 C18 124.46(12) . . ?
C15 N14 C13 111.53(11) . . ?
C15 N14 C18 123.92(12) . . ?
C5 C10 C1 116.75(11) . . ?
C9 C10 C5 119.69(11) . . ?
C9 C10 C1 123.10(11) . . ?
C31 C26 C25 120.99(12) . . ?
C27 C26 C25 120.27(11) . . ?
C27 C26 C31 118.71(12) . . ?
C10 C5 C4 119.00(11) . . ?
C6 C5 C10 119.36(13) . . ?
C6 C5 C4 121.62(12) . . ?
C20 C2 C1 112.51(10) . . ?
C3 C2 C20 113.43(11) . . ?
C3 C2 C1 107.56(9) . . ?
O17 C13 N12 127.32(13) . . ?
O17 C13 N14 126.85(12) . . ?
N12 C13 N14 105.83(11) . . ?
C20 C25 C26 122.20(11) . . ?
C24 C25 C26 118.86(11) . . ?
C24 C25 C20 118.93(12) . . ?
C25 C20 C2 121.37(11) . . ?
C21 C20 C2 119.72(11) . . ?
C21 C20 C25 118.85(11) . . ?
N11 C1 C10 113.20(10) . . ?
N11 C1 C2 112.50(9) . . ?
C10 C1 C2 111.55(10) . . ?
O19 C15 N11 126.13(12) . . ?
O19 C15 N14 127.53(12) . . ?
N14 C15 N11 106.32(11) . . ?
C10 C9 C8 120.21(13) . . ?
C7 C8 C9 120.43(13) . . ?
C30 C31 C26 119.99(13) . . ?
C28 C27 C26 121.06(12) . . ?
C3 C4 C5 121.29(12) . . ?
C29 C28 C27 119.84(13) . . ?
C4 C3 C2 121.31(12) . . ?
C7 C6 C5 120.63(13) . . ?
C8 C7 C6 119.68(12) . . ?
C23 C24 C25 121.25(12) . . ?
C22 C21 C20 121.35(12) . . ?
C30 C29 C28 119.48(13) . . ?
C29 C30 C31 120.91(13) . . ?
C23 C22 C21 119.82(12) . . ?
C22 C23 C24 119.69(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.436
_oxdiff_exptl_absorpt_empirical_full_min 0.514
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/pentane'
####################################################################### 
# 
# 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_knm-039a-gpcfr1-acoet_pentane
_database_code_depnum_ccdc_archive 'CCDC 2506078'
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2021-10-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'compound 5'
_chemical_formula_moiety         'C25 H21 N3 O2'
_chemical_formula_sum            'C25 H21 N3 O2'
_chemical_formula_weight         395.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.9010(14)
_cell_length_b                   10.1314(7)
_cell_length_c                   13.5202(11)
_cell_angle_alpha                90
_cell_angle_beta                 104.524(9)
_cell_angle_gamma                90
_cell_volume                     1975.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4080
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.8580
_cell_measurement_theta_min      2.4420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47398
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.39a (Rigaku Oxford Diffraction, 2019)
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    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1360
_diffrn_reflns_av_unetI/netI     0.1109
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14826
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.153
_diffrn_reflns_theta_min         2.457
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00  92.00   0.50  140.00    --    8.30   9.00 -75.00  326
  2  ω     13.00  39.00   0.50  140.00    --   -7.75  37.00-180.00   52
  3  ω    -23.00   8.00   0.50  140.00    --   -7.75  37.00-180.00   62
  4  ω    -13.00  39.00   0.50  140.00    --   -7.75 -99.00  30.00  104
  5  ω    -15.00  22.00   0.50  140.00    --    8.30 -99.00  90.00   74
  6  ω     67.00  92.00   0.50  140.00    --    8.30 179.00  60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0116729000
_diffrn_orient_matrix_UB_12      -0.0079311000
_diffrn_orient_matrix_UB_13      -0.0473961000
_diffrn_orient_matrix_UB_21      0.0476666000
_diffrn_orient_matrix_UB_22      -0.0021685000
_diffrn_orient_matrix_UB_23      0.0258873000
_diffrn_orient_matrix_UB_31      -0.0027712000
_diffrn_orient_matrix_UB_32      -0.0695254000
_diffrn_orient_matrix_UB_33      0.0047320000
_diffrn_oxdiff_digest_frames     
;
01df15bb22b38074db78e7bca69f6d3907000258f82
;
_diffrn_oxdiff_digest_hkl        
;
01f2c1fffa98b4e29ef75316ac33b81491e8df
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2285
_reflns_number_total             4031
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.01
_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 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.39a (Rigaku OD, 2019)'
_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         0.420
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1325
_refine_ls_R_factor_gt           0.0729
_refine_ls_restrained_S_all      0.987
_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)+(0.1219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1769
_refine_ls_wR_factor_ref         0.2126
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C1(H1)
2.b Aromatic/amide H refined with riding coordinates:
 N24(H27), C9(H9), C12(H15), C3(H3), C15(H12), C13(H14), C22(H18), C6(H6),
 C18(H22), C10(H10), C4(H4), C14(H13), C5(H5), C21(H19), C19(H21), C20(H20)
2.c Idealised Me refined as rotating group:
 C28(H30A,H30B,H30C)
;
_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
O28 O 0.51631(16) 0.1656(2) 0.36613(16) 0.0390(6) Uani 1 1 d . . . . .
O29 O 0.41695(15) 0.5915(2) 0.38091(16) 0.0404(6) Uani 1 1 d . . . . .
N23 N 0.54605(18) 0.3616(2) 0.29027(18) 0.0319(6) Uani 1 1 d . . . . .
N27 N 0.52388(18) 0.4950(2) 0.30582(19) 0.0320(6) Uani 1 1 d . . . . .
H27 H 0.547400 0.563246 0.284089 0.038 Uiso 1 1 calc R . . . .
N25 N 0.45107(17) 0.3681(2) 0.39125(17) 0.0322(6) Uani 1 1 d . . . . .
C26 C 0.4592(2) 0.4963(3) 0.3609(2) 0.0314(7) Uani 1 1 d . . . . .
C24 C 0.5059(2) 0.2855(3) 0.3509(2) 0.0327(7) Uani 1 1 d . . . . .
C11 C 0.8292(2) 0.7855(3) 0.2528(2) 0.0310(7) Uani 1 1 d . . . . .
C16 C 0.7690(2) 0.6927(3) 0.2794(2) 0.0297(7) Uani 1 1 d . . . . .
C8 C 0.6389(2) 0.3352(3) 0.2765(2) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.643675 0.239675 0.267740 0.037 Uiso 1 1 calc R . . . .
C17 C 0.9030(2) 0.7499(3) 0.2006(2) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.6471(2) 0.3987(3) 0.1794(2) 0.0328(7) Uani 1 1 d . . . . .
H9 H 0.606900 0.371075 0.118669 0.039 Uiso 1 1 calc R . . . .
C2 C 0.7809(2) 0.4704(3) 0.3621(2) 0.0306(7) Uani 1 1 d . . . . .
C15 C 0.7014(2) 0.7373(3) 0.3254(2) 0.0337(7) Uani 1 1 d . . . . .
H15 H 0.661007 0.676128 0.342106 0.040 Uiso 1 1 calc R . . . .
C30 C 0.3911(2) 0.3251(3) 0.4549(2) 0.0403(8) Uani 1 1 d . . . . .
H30A H 0.361115 0.400427 0.475542 0.060 Uiso 1 1 calc GR . . . .
H30B H 0.427426 0.280932 0.514392 0.060 Uiso 1 1 calc GR . . . .
H30C H 0.345033 0.265575 0.416887 0.060 Uiso 1 1 calc GR . . . .
C3 C 0.8515(2) 0.5005(3) 0.4489(2) 0.0353(7) Uani 1 1 d . . . . .
H3 H 0.895394 0.564243 0.444874 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8196(2) 0.9185(3) 0.2776(2) 0.0370(8) Uani 1 1 d . . . . .
H12 H 0.860145 0.980540 0.262341 0.044 Uiso 1 1 calc R . . . .
C1 C 0.7796(2) 0.5449(3) 0.2641(2) 0.0320(7) Uani 1 1 d . . . . .
H1 H 0.840188 0.531511 0.249617 0.038 Uiso 1 1 calc R . . . .
C14 C 0.6916(2) 0.8686(3) 0.3474(2) 0.0376(8) Uani 1 1 d . . . . .
H14 H 0.645013 0.895808 0.377601 0.045 Uiso 1 1 calc R . . . .
C18 C 0.8810(2) 0.6907(3) 0.1041(2) 0.0365(8) Uani 1 1 d . . . . .
H18 H 0.819579 0.669980 0.073303 0.044 Uiso 1 1 calc R . . . .
C7 C 0.7163(2) 0.3748(3) 0.3689(2) 0.0318(7) Uani 1 1 d . . . . .
C6 C 0.7226(2) 0.3112(3) 0.4620(2) 0.0377(8) Uani 1 1 d . . . . .
H6 H 0.679427 0.246717 0.466753 0.045 Uiso 1 1 calc R . . . .
C22 C 0.9942(2) 0.7801(3) 0.2436(2) 0.0393(8) Uani 1 1 d . . . . .
H22 H 1.010544 0.819405 0.307739 0.047 Uiso 1 1 calc R . . . .
C10 C 0.7078(2) 0.4912(3) 0.1746(2) 0.0347(8) Uani 1 1 d . . . . .
H10 H 0.706048 0.526258 0.110597 0.042 Uiso 1 1 calc R . . . .
C4 C 0.8569(2) 0.4367(3) 0.5408(2) 0.0409(8) Uani 1 1 d . . . . .
H4 H 0.904319 0.457212 0.597844 0.049 Uiso 1 1 calc R . . . .
C13 C 0.7527(2) 0.9593(3) 0.3235(2) 0.0382(8) Uani 1 1 d . . . . .
H13 H 0.748096 1.048135 0.338869 0.046 Uiso 1 1 calc R . . . .
C5 C 0.7924(2) 0.3433(3) 0.5475(2) 0.0421(8) Uani 1 1 d . . . . .
H5 H 0.795374 0.301393 0.609444 0.050 Uiso 1 1 calc R . . . .
C19 C 0.9478(3) 0.6625(3) 0.0542(2) 0.0426(8) Uani 1 1 d . . . . .
H19 H 0.931332 0.622399 -0.009712 0.051 Uiso 1 1 calc R . . . .
C21 C 1.0623(2) 0.7532(3) 0.1934(3) 0.0430(8) Uani 1 1 d . . . . .
H21 H 1.123595 0.775202 0.223690 0.052 Uiso 1 1 calc R . . . .
C20 C 1.0393(3) 0.6932(3) 0.0976(3) 0.0437(9) Uani 1 1 d . . . . .
H20 H 1.084889 0.674165 0.063675 0.052 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
O28 C24 1.235(4) . ?
O29 C26 1.218(4) . ?
N23 N27 1.419(3) . ?
N23 C24 1.368(4) . ?
N23 C8 1.466(4) . ?
N27 C26 1.358(4) . ?
N25 C26 1.377(4) . ?
N25 C24 1.375(4) . ?
N25 C30 1.455(4) . ?
C11 C16 1.406(4) . ?
C11 C17 1.493(4) . ?
C11 C12 1.404(4) . ?
C16 C15 1.386(4) . ?
C16 C1 1.525(4) . ?
C8 C9 1.494(4) . ?
C8 C7 1.527(4) . ?
C17 C18 1.398(4) . ?
C17 C22 1.372(4) . ?
C9 C10 1.315(4) . ?
C2 C3 1.400(4) . ?
C2 C1 1.521(4) . ?
C2 C7 1.384(4) . ?
C15 C14 1.380(4) . ?
C3 C4 1.385(4) . ?
C12 C13 1.364(5) . ?
C1 C10 1.502(4) . ?
C14 C13 1.388(5) . ?
C18 C19 1.365(5) . ?
C7 C6 1.397(4) . ?
C6 C5 1.386(4) . ?
C22 C21 1.381(5) . ?
C4 C5 1.367(5) . ?
C19 C20 1.379(5) . ?
C21 C20 1.394(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N27 N23 C8 117.1(2) . . ?
C24 N23 N27 107.2(2) . . ?
C24 N23 C8 122.8(2) . . ?
C26 N27 N23 108.3(2) . . ?
C26 N25 C30 124.8(3) . . ?
C24 N25 C26 110.5(2) . . ?
C24 N25 C30 124.6(3) . . ?
O29 C26 N27 127.4(3) . . ?
O29 C26 N25 126.3(3) . . ?
N27 C26 N25 106.3(2) . . ?
O28 C24 N23 126.8(3) . . ?
O28 C24 N25 126.5(3) . . ?
N23 C24 N25 106.7(3) . . ?
C16 C11 C17 123.5(3) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 C17 118.4(3) . . ?
C11 C16 C1 121.9(3) . . ?
C15 C16 C11 118.6(3) . . ?
C15 C16 C1 119.4(3) . . ?
N23 C8 C9 108.7(2) . . ?
N23 C8 C7 113.1(2) . . ?
C9 C8 C7 113.2(3) . . ?
C18 C17 C11 121.1(3) . . ?
C22 C17 C11 121.0(3) . . ?
C22 C17 C18 117.8(3) . . ?
C10 C9 C8 124.0(3) . . ?
C3 C2 C1 117.7(3) . . ?
C7 C2 C3 119.1(3) . . ?
C7 C2 C1 123.3(3) . . ?
C14 C15 C16 122.6(3) . . ?
C4 C3 C2 120.8(3) . . ?
C13 C12 C11 121.9(3) . . ?
C2 C1 C16 110.4(2) . . ?
C10 C1 C16 112.8(2) . . ?
C10 C1 C2 111.9(2) . . ?
C15 C14 C13 118.5(3) . . ?
C19 C18 C17 121.5(3) . . ?
C2 C7 C8 121.7(2) . . ?
C2 C7 C6 119.5(3) . . ?
C6 C7 C8 118.8(3) . . ?
C5 C6 C7 120.7(3) . . ?
C17 C22 C21 121.3(3) . . ?
C9 C10 C1 125.3(3) . . ?
C5 C4 C3 120.0(3) . . ?
C12 C13 C14 120.2(3) . . ?
C4 C5 C6 120.0(3) . . ?
C18 C19 C20 120.5(3) . . ?
C22 C21 C20 120.2(3) . . ?
C19 C20 C21 118.7(3) . . ?

_olex2_exptl_crystal_mounting_method 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 3.274
_oxdiff_exptl_absorpt_empirical_full_min 0.447
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/pentane'
####################################################################### 
# 
# 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_knm309d_etoac_hexane_x-ray_auto
_database_code_depnum_ccdc_archive 'CCDC 2506076'
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2023-08-25
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'compound 8'
_chemical_formula_moiety         'C25.04 H20.04 I N3 O2'
_chemical_formula_sum            'C25.04 H20.04 I N3 O2'
_chemical_formula_weight         521.86
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N O I H'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.3604(10)
_cell_length_b                   9.5211(7)
_cell_length_c                   15.3873(10)
_cell_angle_alpha                90
_cell_angle_beta                 107.325(7)
_cell_angle_gamma                90
_cell_volume                     2148.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6713
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.7690
_cell_measurement_theta_min      2.5520
_shelx_estimated_absorpt_T_max   0.804
_shelx_estimated_absorpt_T_min   0.751
_exptl_absorpt_coefficient_mu    1.518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1041
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.773
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11670
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.832
_diffrn_reflns_theta_min         2.549
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.773
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  21.00   0.50    1.91    --    3.32 -62.00 164.00   74
  2  ω    -42.00  20.00   0.50    1.91    --   -2.70 -90.00  61.00  124
  3  ω    -20.00  13.00   0.50    1.91    --   -2.70 -57.00-120.00   66
  4  ω    -68.00 -33.00   0.50    1.91    --   -2.70 -57.00-120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0183347000
_diffrn_orient_matrix_UB_12      -0.0329024000
_diffrn_orient_matrix_UB_13      -0.0430451000
_diffrn_orient_matrix_UB_21      0.0118239000
_diffrn_orient_matrix_UB_22      0.0596553000
_diffrn_orient_matrix_UB_23      -0.0216261000
_diffrn_orient_matrix_UB_31      0.0431161000
_diffrn_orient_matrix_UB_32      -0.0302259000
_diffrn_orient_matrix_UB_33      0.0037589000
_diffrn_oxdiff_digest_frames     
;
016292a47c11436f2809e437f24419183800026855d
;
_diffrn_oxdiff_digest_hkl        
;
01e4750afd15e599cc9bee88f71dfbc660b347
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3803
_reflns_number_total             4771
_reflns_odcompleteness_completeness 97.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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         0.744
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4771
_refine_ls_number_restraints     96
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.167
_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)+9.5741P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1270
_refine_ls_wR_factor_ref         0.1307
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C25-C26 = C29-C28 = C28-C27 = C27-C26
 1.4 with sigma of 0.01
 C26-C28
 2.4 with sigma of 0.01
 C27-C29
 2.4 with sigma of 0.01
 C29-C25
 2.4 with sigma of 0.01
 C25-C27
 2.4 with sigma of 0.01
 C37-C32 = C37-C36 = C35-C36 = C34-C35 = C33-C34 = C33-C32
 1.4 with sigma of 0.01
 C32-C36
 2.4 with sigma of 0.01
 C37-C35
 2.4 with sigma of 0.01
 C36-C34
 2.4 with sigma of 0.01
 C35-C33
 2.4 with sigma of 0.01
 C34-C32
 2.4 with sigma of 0.01
 C33-C37
 2.4 with sigma of 0.01
3. Restrained planarity
 C34, C33, I38, C32, C37, C36, C35
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C32 \\sim C33 \\sim C34 \\sim C35 \\sim C36 \\sim C37: within 1.7A with sigma
of 0.01 and sigma for terminal atoms of 0.01
Uanis(C32) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
5. Others
 Sof(C32)=Sof(C36)=Sof(H00W)=Sof(C35)=Sof(H1AA)=Sof(C34)=Sof(H2AA)=Sof(C33)=
 Sof(I38)=1-FVAR(1)
 Sof(I31)=Sof(C26)=Sof(C27)=Sof(H00S)=Sof(C25)=Sof(C28)=Sof(H00U)=Sof(C29)=
 Sof(H00V)=Sof(C30)=Sof(H1)=FVAR(1)
 Sof(C37)=Sof(H1A)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C1(H00C), C4(H00O)
6.b Aromatic/amide H refined with riding coordinates:
 N12(H007), C3(H00D), C6(H00E), C2(H00F), C7(H00G), C9(H00I), C22(H00J),
 C24(H00K), C23(H00N), C8(H00P), C21(H00Q), C27(H00S), C28(H00U), C29(H00V),
 C30(H1), C37(H1A), C36(H00W), C35(H1AA), C34(H2AA)
6.c Idealised Me refined as rotating group:
 C17(H00A,H00B,H00H)
;
_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
I31 I 0.96271(3) 0.16586(6) 0.71296(3) 0.04182(17) Uani 0.8896(18) 1 d . . P A
1
O16 O 0.4746(2) 0.5026(4) 0.3727(2) 0.0286(8) Uani 1 1 d . . . . .
O18 O 0.6088(2) 0.9331(4) 0.3797(2) 0.0272(8) Uani 1 1 d . . . . .
N14 N 0.5322(3) 0.7212(4) 0.3490(3) 0.0225(9) Uani 1 1 d . . . . .
N11 N 0.6109(3) 0.7682(4) 0.4924(3) 0.0196(8) Uani 1 1 d . . . . .
N12 N 0.5761(3) 0.6301(4) 0.4860(3) 0.0207(8) Uani 1 1 d . . . . .
H007 H 0.587664 0.569192 0.530954 0.025 Uiso 1 1 calc R . . . .
C13 C 0.5222(3) 0.6056(5) 0.4001(3) 0.0204(9) Uani 1 1 d . . . . .
C19 C 0.7419(3) 0.3663(5) 0.6221(3) 0.0201(9) Uani 1 1 d . . . . .
C5 C 0.8078(3) 0.5632(5) 0.5483(3) 0.0206(10) Uani 1 1 d . . . . .
C15 C 0.5862(3) 0.8212(5) 0.4035(3) 0.0209(9) Uani 1 1 d . . . . .
C1 C 0.7093(3) 0.7771(5) 0.5484(3) 0.0190(9) Uani 1 1 d . . . . .
H00C H 0.729264 0.877321 0.549984 0.023 Uiso 1 1 calc R . . . .
C3 C 0.7469(3) 0.6124(5) 0.6802(3) 0.0226(10) Uani 1 1 d . . . . .
H00D H 0.742247 0.590678 0.738903 0.027 Uiso 1 1 calc R . . . .
C6 C 0.8653(3) 0.4893(5) 0.5090(3) 0.0257(10) Uani 1 1 d . . . . .
H00E H 0.892691 0.404339 0.536388 0.031 Uiso 1 1 calc R . . . .
C2 C 0.7128(3) 0.7338(5) 0.6429(3) 0.0228(10) Uani 1 1 d . . . . .
H00F H 0.689336 0.796841 0.678201 0.027 Uiso 1 1 calc R . . . .
C7 C 0.8830(3) 0.5372(6) 0.4315(3) 0.0272(11) Uani 1 1 d . . . . .
H00G H 0.921639 0.484807 0.405527 0.033 Uiso 1 1 calc R . . . .
C10 C 0.7699(3) 0.6893(5) 0.5082(3) 0.0208(10) Uani 1 1 d . . . . .
C9 C 0.7895(3) 0.7388(6) 0.4302(3) 0.0256(10) Uani 1 1 d . . . . .
H00I H 0.764819 0.825778 0.403877 0.031 Uiso 1 1 calc R . . . .
C22 C 0.6423(3) 0.1149(6) 0.6004(4) 0.0276(11) Uani 1 1 d . . . . .
H00J H 0.607886 0.030501 0.593018 0.033 Uiso 1 1 calc R . . . .
C24 C 0.6791(3) 0.3298(5) 0.5385(3) 0.0252(10) Uani 1 1 d . . . . .
H00K H 0.669904 0.391594 0.488095 0.030 Uiso 1 1 calc R . . . .
C20 C 0.7547(3) 0.2731(5) 0.6948(3) 0.0261(11) Uani 1 1 d . . . . .
C17 C 0.4900(4) 0.7343(6) 0.2513(3) 0.0288(11) Uani 1 1 d . . . . .
H00A H 0.482926 0.640896 0.223281 0.043 Uiso 1 1 calc GR . . . .
H00B H 0.528744 0.792281 0.225237 0.043 Uiso 1 1 calc GR . . . .
H00H H 0.430027 0.778597 0.239425 0.043 Uiso 1 1 calc GR . . . .
C23 C 0.6307(3) 0.2070(6) 0.5282(3) 0.0280(11) Uani 1 1 d . . . . .
H00N H 0.588748 0.184649 0.470764 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7927(3) 0.5065(5) 0.6350(3) 0.0211(10) Uani 1 1 d . . . . .
H00O H 0.854501 0.488716 0.678445 0.025 Uiso 1 1 calc R . . . .
C8 C 0.8445(3) 0.6615(6) 0.3913(3) 0.0296(11) Uani 1 1 d . . . . .
H00P H 0.855884 0.693704 0.337265 0.036 Uiso 1 1 calc R . . . .
C21 C 0.7046(4) 0.1472(6) 0.6834(4) 0.0304(11) Uani 1 1 d . . . . .
H00Q H 0.713584 0.084027 0.733117 0.036 Uiso 1 1 calc R . . . .
C26 C 0.9124(3) 0.2694(6) 0.8079(3) 0.0238(11) Uani 0.8896(18) 1 d D . P A 1
C27 C 0.9727(3) 0.2967(7) 0.8935(3) 0.0295(14) Uani 0.8896(18) 1 d D . P A 1
H00S H 1.035714 0.275676 0.905666 0.035 Uiso 0.8896(18) 1 calc R . P A 1
C25 C 0.8201(3) 0.3016(5) 0.7879(3) 0.0200(11) Uani 0.8896(18) 1 d D . P A 1
C28 C 0.9410(4) 0.3546(6) 0.9612(3) 0.0321(14) Uani 0.8896(18) 1 d D . P A 1
H00U H 0.981958 0.374493 1.019589 0.039 Uiso 0.8896(18) 1 calc R . P A 1
C29 C 0.8484(4) 0.3829(6) 0.9424(3) 0.0320(14) Uani 0.8896(18) 1 d D . P A 1
H00V H 0.825394 0.418482 0.988974 0.038 Uiso 0.8896(18) 1 calc R . P A 1
C30 C 0.7901(6) 0.3597(7) 0.8568(5) 0.0271(14) Uani 0.8896(18) 1 d . . P A 1
H1 H 0.727588 0.383948 0.844214 0.033 Uiso 0.8896(18) 1 calc R . P A 1
C32 C 0.8664(13) 0.277(3) 0.7564(17) 0.017(5) Uani 0.1104(18) 1 d D U P A 2
C37 C 0.9462(15) 0.246(3) 0.7358(13) 0.020(6) Uani 0.149(16) 1 d D U P A 2
H1A H 0.943402 0.211968 0.676904 0.024 Uiso 0.149(16) 1 calc R . P A 2
C36 C 1.0304(13) 0.263(4) 0.8012(17) 0.025(6) Uani 0.1104(18) 1 d D U P A 2
H00W H 1.085171 0.252387 0.785208 0.030 Uiso 0.1104(18) 1 calc R . P A 2
C35 C 1.0338(16) 0.297(4) 0.8903(15) 0.025(6) Uani 0.1104(18) 1 d D U P A 2
H1AA H 1.090594 0.297553 0.936884 0.030 Uiso 0.1104(18) 1 calc R . P A 2
C34 C 0.954(2) 0.329(4) 0.9108(15) 0.020(6) Uani 0.1104(18) 1 d D U P A 2
H2AA H 0.956569 0.358809 0.970469 0.024 Uiso 0.1104(18) 1 calc R . P A 2
C33 C 0.8703(16) 0.3175(16) 0.8443(18) 0.019(5) Uani 0.1104(18) 1 d D U P A 2
I38 I 0.7543(3) 0.3617(4) 0.8802(2) 0.0302(12) Uani 0.1104(18) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I31 C26 2.092(5) . ?
O16 C13 1.221(6) . ?
O18 C15 1.211(6) . ?
N14 C13 1.388(6) . ?
N14 C15 1.373(6) . ?
N14 C17 1.454(6) . ?
N11 N12 1.411(6) . ?
N11 C15 1.400(6) . ?
N11 C1 1.503(6) . ?
N12 C13 1.354(6) . ?
C19 C24 1.403(7) . ?
C19 C20 1.395(7) . ?
C19 C4 1.529(7) . ?
C5 C6 1.399(7) . ?
C5 C10 1.396(7) . ?
C5 C4 1.519(6) . ?
C1 C2 1.498(6) . ?
C1 C10 1.513(6) . ?
C3 C2 1.326(7) . ?
C3 C4 1.512(7) . ?
C6 C7 1.378(7) . ?
C7 C8 1.383(8) . ?
C10 C9 1.403(6) . ?
C9 C8 1.384(7) . ?
C22 C23 1.385(7) . ?
C22 C21 1.384(7) . ?
C24 C23 1.369(8) . ?
C20 C21 1.406(7) . ?
C20 C25 1.509(7) . ?
C20 C32 1.695(19) . ?
C26 C27 1.391(6) . ?
C26 C25 1.392(6) . ?
C27 C28 1.390(6) . ?
C25 C30 1.390(10) . ?
C28 C29 1.391(6) . ?
C29 C30 1.373(8) . ?
C32 C37 1.388(9) . ?
C32 C33 1.390(9) . ?
C37 C36 1.392(9) . ?
C36 C35 1.393(9) . ?
C35 C34 1.389(9) . ?
C34 C33 1.388(9) . ?
C33 I38 2.06(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N14 C17 124.3(4) . . ?
C15 N14 C13 110.6(4) . . ?
C15 N14 C17 125.1(4) . . ?
N12 N11 C1 112.9(4) . . ?
C15 N11 N12 106.2(4) . . ?
C15 N11 C1 118.2(4) . . ?
C13 N12 N11 109.8(4) . . ?
O16 C13 N14 126.6(4) . . ?
O16 C13 N12 127.2(4) . . ?
N12 C13 N14 106.1(4) . . ?
C24 C19 C4 121.3(4) . . ?
C20 C19 C24 118.2(4) . . ?
C20 C19 C4 120.5(4) . . ?
C6 C5 C4 118.8(4) . . ?
C10 C5 C6 118.4(4) . . ?
C10 C5 C4 122.8(4) . . ?
O18 C15 N14 126.9(4) . . ?
O18 C15 N11 126.5(4) . . ?
N14 C15 N11 106.6(4) . . ?
N11 C1 C10 111.8(4) . . ?
C2 C1 N11 106.2(4) . . ?
C2 C1 C10 113.3(4) . . ?
C2 C3 C4 124.0(4) . . ?
C7 C6 C5 121.3(5) . . ?
C3 C2 C1 123.8(4) . . ?
C6 C7 C8 120.2(5) . . ?
C5 C10 C1 121.4(4) . . ?
C5 C10 C9 120.0(4) . . ?
C9 C10 C1 118.6(4) . . ?
C8 C9 C10 120.4(5) . . ?
C21 C22 C23 119.2(5) . . ?
C23 C24 C19 121.3(5) . . ?
C19 C20 C21 120.1(5) . . ?
C19 C20 C25 122.8(4) . . ?
C19 C20 C32 108.1(11) . . ?
C21 C20 C25 117.1(4) . . ?
C21 C20 C32 121.0(12) . . ?
C24 C23 C22 120.8(5) . . ?
C5 C4 C19 113.7(4) . . ?
C3 C4 C19 110.6(4) . . ?
C3 C4 C5 112.4(4) . . ?
C7 C8 C9 119.7(5) . . ?
C22 C21 C20 120.4(5) . . ?
C27 C26 I31 117.9(4) . . ?
C27 C26 C25 121.1(4) . . ?
C25 C26 I31 120.9(3) . . ?
C28 C27 C26 120.0(5) . . ?
C26 C25 C20 121.1(4) . . ?
C30 C25 C20 121.1(5) . . ?
C30 C25 C26 117.8(5) . . ?
C27 C28 C29 119.2(4) . . ?
C30 C29 C28 120.1(6) . . ?
C29 C30 C25 121.8(7) . . ?
C37 C32 C20 133.1(16) . . ?
C37 C32 C33 119.8(7) . . ?
C33 C32 C20 107.1(16) . . ?
C32 C37 C36 120.2(8) . . ?
C37 C36 C35 119.6(8) . . ?
C34 C35 C36 119.8(8) . . ?
C33 C34 C35 120.1(8) . . ?
C32 C33 I38 121.8(16) . . ?
C34 C33 C32 120.1(7) . . ?
C34 C33 I38 118.1(15) . . ?

_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 1.301
_oxdiff_exptl_absorpt_empirical_full_min 0.805
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/hexane'
####################################################################### 
# 
# 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_knm441a_gpc2-fr2_cs2-pentane_x-ray_auto
_database_code_depnum_ccdc_archive 'CCDC 2506077'
loop_
_audit_author_name
_audit_author_address
'Hideto Ito'
;Nagoya University
Japan
;
_audit_update_record             
;
2025-11-27 deposited with the CCDC.	2026-01-28 downloaded from the CCDC.
;
_audit_creation_date             2024-02-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.05 svn.r3537 for Rigaku Oxford Diffraction, GUI svn.r5625)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'tribenzo[a,c,j]picene (compound 11)'
_chemical_formula_moiety         'C17 H10'
_chemical_formula_sum            'C17 H10'
_chemical_formula_weight         214.25
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.780(3)
_cell_length_b                   3.8860(4)
_cell_length_c                   19.6341(18)
_cell_angle_alpha                90
_cell_angle_beta                 102.831(10)
_cell_angle_gamma                90
_cell_volume                     1992.2(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2508
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      29.2690
_cell_measurement_theta_min      2.3430
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26286
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CS2/pentane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0479
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.823
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6881
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.823
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.577
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.823
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  32.00   0.50   25.00    --   -2.54  57.00-180.00   94
  2  ω    -20.00   6.00   0.50   25.00    --   -2.54 -19.00 120.00   52
  3  ω    -51.00   8.00   0.50   25.00    --   -2.54 -57.00 -60.00  118
  4  ω    -11.00  35.00   0.50   25.00    --    3.16 -99.00 -60.00   92
  5  ω    -11.00  38.00   0.50   25.00    --    3.16 -99.00-180.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0145604000
_diffrn_orient_matrix_UB_12      0.1540411000
_diffrn_orient_matrix_UB_13      -0.0046194000
_diffrn_orient_matrix_UB_21      0.0228715000
_diffrn_orient_matrix_UB_22      0.0975977000
_diffrn_orient_matrix_UB_23      0.0097437000
_diffrn_orient_matrix_UB_31      0.0018847000
_diffrn_orient_matrix_UB_32      0.0067767000
_diffrn_orient_matrix_UB_33      -0.0354425000
_diffrn_oxdiff_digest_frames     
;
01a52dc06e079a15d2989cafe9ff799b6f00025a2ee
;
_diffrn_oxdiff_digest_hkl        01c6962592cc8a956093c4f6494a226581a990
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1797
_reflns_number_total             2311
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)'
_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         0.362
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.056
_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)+(0.0772P)²+0.8857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H002), C2(H008), C5(H00A), C13(H00B), C6(H00C), C14(H00D), C12(H00E),
 C11(H00F), C8(H00G), C7(H00H)
;
_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
C3 C 0.54826(5) 0.5580(4) 0.37712(7) 0.0141(3) Uani 1 1 d . . . . .
C1 C 0.45926(6) 0.5359(4) 0.31439(7) 0.0156(3) Uani 1 1 d . . . . .
H002 H 0.424056 0.534428 0.315929 0.019 Uiso 1 1 calc R . . . .
C16 C 0.56403(5) 0.4646(4) 0.31621(7) 0.0133(3) Uani 1 1 d . . . . .
C4 C 0.58617(5) 0.6300(4) 0.44144(7) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.63865(5) 0.5783(4) 0.44408(7) 0.0148(3) Uani 1 1 d . . . . .
C10 C 0.65428(5) 0.4244(4) 0.38411(7) 0.0149(3) Uani 1 1 d . . . . .
C15 C 0.61728(5) 0.3625(4) 0.32178(7) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.49505(6) 0.5942(4) 0.37386(7) 0.0160(3) Uani 1 1 d . . . . .
H008 H 0.484145 0.661700 0.414748 0.019 Uiso 1 1 calc R . . . .
C17 C 0.47345(5) 0.4765(4) 0.24949(7) 0.0138(3) Uani 1 1 d . . . . .
C5 C 0.57180(6) 0.7677(4) 0.50054(7) 0.0184(3) Uani 1 1 d . . . . .
H00A H 0.536493 0.800571 0.499530 0.022 Uiso 1 1 calc R . . . .
C13 C 0.68289(6) 0.0792(4) 0.27320(7) 0.0189(3) Uani 1 1 d . . . . .
H00B H 0.692308 -0.042103 0.235954 0.023 Uiso 1 1 calc R . . . .
C6 C 0.60756(6) 0.8560(4) 0.55972(7) 0.0196(4) Uani 1 1 d . . . . .
H00C H 0.596902 0.950100 0.598848 0.023 Uiso 1 1 calc R . . . .
C14 C 0.63275(6) 0.1749(4) 0.26837(7) 0.0168(3) Uani 1 1 d . . . . .
H00D H 0.607753 0.112823 0.227853 0.020 Uiso 1 1 calc R . . . .
C12 C 0.71976(6) 0.1611(4) 0.33299(8) 0.0196(4) Uani 1 1 d . . . . .
H00E H 0.754689 0.104376 0.335983 0.024 Uiso 1 1 calc R . . . .
C11 C 0.70535(5) 0.3244(4) 0.38757(7) 0.0181(3) Uani 1 1 d . . . . .
H00F H 0.730526 0.371344 0.428862 0.022 Uiso 1 1 calc R . . . .
C8 C 0.67451(6) 0.6690(4) 0.50552(7) 0.0188(3) Uani 1 1 d . . . . .
H00G H 0.709947 0.633737 0.507818 0.023 Uiso 1 1 calc R . . . .
C7 C 0.65943(6) 0.8072(4) 0.56214(7) 0.0203(4) Uani 1 1 d . . . . .
H00H H 0.684292 0.869265 0.602789 0.024 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
C3 C16 1.4018(19) . ?
C3 C4 1.4609(19) . ?
C3 C2 1.4192(19) . ?
C1 C2 1.355(2) . ?
C1 C17 1.4269(19) . ?
C16 C15 1.4607(19) . ?
C16 C17 1.4485(19) 2_655 ?
C4 C9 1.409(2) . ?
C4 C5 1.407(2) . ?
C9 C10 1.462(2) . ?
C9 C8 1.410(2) . ?
C10 C15 1.4137(19) . ?
C10 C11 1.409(2) . ?
C15 C14 1.413(2) . ?
C17 C17 1.418(3) 2_655 ?
C5 C6 1.375(2) . ?
C13 C14 1.376(2) . ?
C13 C12 1.393(2) . ?
C6 C7 1.392(2) . ?
C12 C11 1.372(2) . ?
C8 C7 1.374(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16 C3 C4 120.26(13) . . ?
C16 C3 C2 118.48(12) . . ?
C2 C3 C4 121.20(12) . . ?
C2 C1 C17 121.27(13) . . ?
C3 C16 C15 118.71(12) . . ?
C3 C16 C17 118.11(13) . 2_655 ?
C17 C16 C15 123.18(12) 2_655 . ?
C9 C4 C3 120.02(12) . . ?
C5 C4 C3 121.40(13) . . ?
C5 C4 C9 118.50(13) . . ?
C4 C9 C10 119.35(12) . . ?
C4 C9 C8 118.68(13) . . ?
C8 C9 C10 121.94(13) . . ?
C15 C10 C9 119.71(13) . . ?
C11 C10 C9 121.49(13) . . ?
C11 C10 C15 118.76(13) . . ?
C10 C15 C16 120.24(12) . . ?
C14 C15 C16 121.79(12) . . ?
C14 C15 C10 117.75(13) . . ?
C1 C2 C3 122.22(13) . . ?
C1 C17 C16 122.08(13) . 2_655 ?
C17 C17 C1 116.90(15) 2_655 . ?
C17 C17 C16 120.47(15) 2_655 2_655 ?
C6 C5 C4 121.69(14) . . ?
C14 C13 C12 119.64(14) . . ?
C5 C6 C7 119.80(13) . . ?
C13 C14 C15 122.05(13) . . ?
C11 C12 C13 119.61(13) . . ?
C12 C11 C10 121.89(13) . . ?
C7 C8 C9 121.57(14) . . ?
C8 C7 C6 119.74(13) . . ?

_olex2_exptl_crystal_mounting_method 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 2.613
_oxdiff_exptl_absorpt_empirical_full_min 0.622
_exptl_crystal_preparation       Luminescent
