# Supplementary Information (SI) for Green Chemistry.
# 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_1a-abl(pcf3)_auto
_database_code_depnum_ccdc_archive 'CCDC 2468258'
loop_
_audit_author_name
_audit_author_address
'Vijay Kumar Das'
;Banaras Hindu University
India
;
_audit_update_record             
;
2025-06-30 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_audit_creation_date             2025-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H17 F4.717 N2 O, 0.428(F3)'
_chemical_formula_sum            'C28 H17 F6 N2 O'
_chemical_formula_weight         511.43
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N F'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.1816(3)
_cell_length_b                   9.6057(2)
_cell_length_c                   14.0760(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.815(2)
_cell_angle_gamma                90
_cell_volume                     1229.91(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8510
_cell_measurement_theta_min      3.1590
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.003
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             522
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11054
_diffrn_reflns_point_group_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.103
_diffrn_reflns_theta_min         3.169
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.997
_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    -59.00  27.00   0.50    0.38    --  -40.83  52.00 137.00  172
  2  ω   -107.00 -21.00   0.50    0.38    --  -40.83 -52.00  -7.00  172
  3  ω     21.00 109.00   0.50    0.38    --   40.83  52.00 137.00  176
  4  ω   -150.00 -63.00   0.50    1.50    --  -82.50 -52.00  -7.00  174
  5  ω    -59.00 -15.00   0.50    1.50    --  -82.50  52.00 137.00   88
  6  ω     76.00 163.00   0.50    1.50    --   96.04  52.00 137.00  174
  7  ω     28.00  59.00   0.50    1.50    --   96.04 -52.00  -7.00   62
  8  ω   -117.00  -4.00   0.50    0.38    --  -40.83 -11.00-180.00  226
  9  ω     18.00  78.00   0.50    0.38    --   40.83-104.00-180.00  120
 10  ω    -26.00  59.00   0.50    0.38    --   40.83 -52.00  -7.00  170
 11  ω    -25.00  48.00   0.50    0.38    --   40.83 -43.00-120.00  146
 12  ω    -35.00  24.00   0.50    0.38    --   40.83 -11.00-120.00  118
 13  ω    -84.00 -18.00   0.50    1.50    --  -82.50 117.00 -60.00  132
 14  ω    -57.00 -16.00   0.50    1.50    --  -82.50  50.00 -90.00   82
 15  ω     79.00 162.00   0.50    1.50    --   96.04  42.00  90.00  166
 16  ω     29.00  57.00   0.50    1.50    --   96.04 -50.00 120.00   56
 17  ω     28.00  68.00   0.50    1.50    --   96.04 -59.00 -30.00   80
 18  ω     82.00 164.00   0.50    1.50    --   96.04  33.00-120.00  164
 19  ω     28.00  83.00   0.50    1.50    --   96.04 -68.00-150.00  110
 20  ω     77.00 163.00   0.50    1.50    --   96.04  50.00-180.00  172
 21  ω     28.00  83.00   0.50    1.50    --   96.04 -68.00 -60.00  110
 22  ω     28.00  68.00   0.50    1.50    --   96.04 -59.00-150.00   80
 23  ω     28.00  68.00   0.50    1.50    --   96.04 -59.00 150.00   80
 24  ω     28.00  68.00   0.50    1.50    --   96.04 -59.00  30.00   80
 25  ω     44.00 127.00   0.50    1.50    --   96.04-145.00-120.00  166
 26  ω     28.00  68.00   0.50    1.50    --   96.04 -59.00  90.00   80
 27  ω     29.00  57.00   0.50    1.50    --   96.04 -50.00-120.00   56
 28  ω     99.00 160.00   0.50    1.50    --   96.04 117.00-180.00  122
 29  ω     71.00 169.00   0.50    1.50    --   96.04  17.00  60.00  196
 30  ω     82.00 164.00   0.50    1.50    --   96.04  33.00 -90.00  164
 31  ω     29.00  57.00   0.50    1.50    --   96.04 -50.00  60.00   56
 32  ω     28.00  83.00   0.50    1.50    --   96.04 -68.00-120.00  110
 33  ω   -109.00 -14.00   0.50    0.38    --  -40.83 -77.00 -30.00  190
 34  ω   -109.00 -14.00   0.50    0.38    --  -40.83 -77.00  60.00  190
 35  ω     14.00 110.00   0.50    0.38    --   40.83  77.00-120.00  192
 36  ω     18.00 109.00   0.50    0.38    --   40.83  65.00-150.00  182
 37  ω     14.00 110.00   0.50    0.38    --   40.83  77.00 -60.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1466804000
_diffrn_orient_matrix_UB_12      -0.0415359000
_diffrn_orient_matrix_UB_13      0.0338409000
_diffrn_orient_matrix_UB_21      0.0837001000
_diffrn_orient_matrix_UB_22      -0.0916552000
_diffrn_orient_matrix_UB_23      0.0791251000
_diffrn_orient_matrix_UB_31      0.0128608000
_diffrn_orient_matrix_UB_32      0.1249175000
_diffrn_orient_matrix_UB_33      0.0692380000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.791
_reflns_Friedel_fraction_max     0.785
_reflns_number_gt                3113
_reflns_number_total             4021
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     355
_refine_ls_number_reflns         4021
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.060
_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)+(0.0939P)²+0.2789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1862
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.4(4)
 0.6(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C2-F5 \\sim C2-F2
 with sigma of 0.04
 C2-F4 \\sim C2-F1
 with sigma of 0.04
 C2-F3 \\sim C2-F6
 with sigma of 0.04
 F5-F4 \\sim F2-F1
 with sigma of 0.04
 F5-F3 \\sim F2-F6
 with sigma of 0.04
 F4-F3 \\sim F1-F6
 with sigma of 0.04
 C28-F7 \\sim C28-F12
 with sigma of 0.02
 C28-F11 \\sim C28-F10
 with sigma of 0.02
 C28-F9 \\sim C28-F8
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C1) = Uanis(F3) = Uanis(F2) = Uanis(F1) = Uanis(F6) = Uanis(F4)
Uanis(F4) = Uanis(F5) = Uanis(F6) = Uanis(F1) = Uanis(F2) = Uanis(F3)
5. Rigid body (RIGU) restrains
 C1, F5, F4, F3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2, F1, F6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(F2)=Sof(F6)=Sof(F1)=1-FVAR(1)
 Sof(F5)=Sof(F4)=Sof(F3)=FVAR(1)
 Sof(F8)=Sof(F12)=Sof(F10)=1-FVAR(2)
 Sof(F7)=Sof(F11)=Sof(F9)=FVAR(2)
7.a Aromatic/amide H refined with riding coordinates:
 C18(H18), C27(H27), C23(H23), C4(H4), C17(H17), C21(H21), C3(H3), C24(H24),
 C26(H26), C6(H6), C20(H20), C19(H19), C11(H11), C12(H12), C15(H15), C13(H13),
 C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7688(4) 0.9302(4) 0.6796(3) 0.0760(11) Uani 1 1 d . . . . .
N2 N 0.7495(5) 0.7093(5) 0.7489(3) 0.0661(10) Uani 1 1 d . . . . .
N1 N 0.7789(5) 0.5907(5) 0.6907(3) 0.0624(10) Uani 1 1 d . . . . .
C9 C 0.7815(6) 0.8068(6) 0.6828(3) 0.0620(12) Uani 1 1 d . . . . .
C16 C 0.9905(5) 0.6966(6) 0.6075(3) 0.0607(11) Uani 1 1 d . . . . .
C22 C 0.6360(5) 0.7120(6) 0.8071(3) 0.0639(12) Uani 1 1 d . . . . .
C5 C 0.8802(6) 0.4916(6) 0.7370(3) 0.0619(12) Uani 1 1 d . . . . .
C25 C 0.4179(6) 0.7208(7) 0.9237(4) 0.0708(14) Uani 1 1 d . . . . .
C1 C 1.1436(14) 0.1686(12) 0.8680(8) 0.145(2) Uani 1 1 d . . . A 1
C18 C 1.1904(7) 0.6468(7) 0.5187(5) 0.0862(18) Uani 1 1 d . . . . .
H18 H 1.224601 0.607773 0.465428 0.103 Uiso 1 1 calc R U . . .
C27 C 0.5610(6) 0.5909(7) 0.8239(4) 0.0697(14) Uani 1 1 d . . . . .
H27 H 0.584475 0.507172 0.796456 0.084 Uiso 1 1 calc R U . . .
C2 C 1.0536(7) 0.2780(7) 0.8230(4) 0.0802(16) Uani 1 1 d D . . . .
C23 C 0.6031(6) 0.8366(7) 0.8489(4) 0.0725(14) Uani 1 1 d . . . . .
H23 H 0.655211 0.917094 0.839035 0.087 Uiso 1 1 calc R U . . .
C10 C 0.7271(6) 0.6849(6) 0.5230(3) 0.0652(13) Uani 1 1 d . . . . .
C4 C 0.9330(6) 0.4974(6) 0.8334(3) 0.0678(13) Uani 1 1 d . . . . .
H4 H 0.911276 0.573366 0.869941 0.081 Uiso 1 1 calc R U . . .
F5 F 1.2124(14) 0.0891(14) 0.8147(9) 0.145(2) Uani 0.572(7) 1 d D . P A 1
C17 C 1.0437(6) 0.6366(6) 0.5293(4) 0.0699(13) Uani 1 1 d . . . . .
H17 H 0.979634 0.589060 0.483626 0.084 Uiso 1 1 calc R U . . .
C8 C 0.8285(5) 0.6919(5) 0.6169(3) 0.0588(11) Uani 1 1 d . . . . .
C21 C 1.0888(6) 0.7618(7) 0.6746(4) 0.0816(17) Uani 1 1 d . . . . .
H21 H 1.055995 0.802656 0.727713 0.098 Uiso 1 1 calc R U . . .
C3 C 1.0182(7) 0.3900(6) 0.8751(4) 0.0791(16) Uani 1 1 d . . . . .
H3 H 1.052533 0.393814 0.940346 0.095 Uiso 1 1 calc R U . . .
C24 C 0.4918(7) 0.8392(7) 0.9054(4) 0.0759(15) Uani 1 1 d . . . . .
H24 H 0.466449 0.923217 0.931641 0.091 Uiso 1 1 calc R U . . .
F4 F 1.2957(12) 0.2042(12) 0.8791(7) 0.145(2) Uani 0.572(7) 1 d D . P A 1
C26 C 0.4508(7) 0.5962(7) 0.8819(4) 0.0772(15) Uani 1 1 d . . . . .
H26 H 0.398882 0.515975 0.892881 0.093 Uiso 1 1 calc R U . . .
C6 C 0.9185(8) 0.3808(6) 0.6845(4) 0.088(2) Uani 1 1 d . . . . .
H6 H 0.883843 0.377205 0.619309 0.106 Uiso 1 1 calc R U . . .
C28 C 0.2999(8) 0.7265(9) 0.9863(5) 0.0928(19) Uani 1 1 d D . . . .
F7 F 0.2492(18) 0.6024(13) 1.0080(13) 0.121(5) Uani 0.65(3) 1 d D . P B 1
F11 F 0.1822(18) 0.785(3) 0.9460(14) 0.161(10) Uani 0.65(3) 1 d D . P B 1
C20 C 1.2363(7) 0.7677(9) 0.6646(5) 0.094(2) Uani 1 1 d . . . . .
H20 H 1.302004 0.809170 0.712403 0.113 Uiso 1 1 calc R U . . .
C7 C 1.0065(10) 0.2747(8) 0.7250(4) 0.101(2) Uani 1 1 d . . . . .
C19 C 1.2861(7) 0.7148(9) 0.5872(5) 0.0908(18) Uani 1 1 d . . . . .
H19 H 1.384717 0.723920 0.579610 0.109 Uiso 1 1 calc R U . . .
C11 C 0.6307(6) 0.5778(9) 0.5005(5) 0.0856(17) Uani 1 1 d . . . . .
H11 H 0.626506 0.504611 0.543239 0.103 Uiso 1 1 calc R U . . .
C12 C 0.5390(8) 0.5788(12) 0.4136(6) 0.110(3) Uani 1 1 d . . . . .
H12 H 0.475898 0.504241 0.397198 0.131 Uiso 1 1 calc R U . . .
C15 C 0.7298(9) 0.7941(8) 0.4596(5) 0.101(2) Uani 1 1 d . . . . .
H15 H 0.795186 0.867230 0.474753 0.121 Uiso 1 1 calc R U . . .
F9 F 0.337(2) 0.786(4) 1.0672(14) 0.191(12) Uani 0.65(3) 1 d D . P B 1
C13 C 0.5408(9) 0.6879(14) 0.3523(6) 0.123(3) Uani 1 1 d . . . . .
H13 H 0.476325 0.688603 0.295274 0.147 Uiso 1 1 calc R U . . .
C14 C 0.6358(11) 0.7963(12) 0.3730(6) 0.127(3) Uani 1 1 d . . . . .
H14 H 0.637838 0.869979 0.330332 0.152 Uiso 1 1 calc R U . . .
F3 F 1.1952(14) 0.1760(12) 0.9589(8) 0.145(2) Uani 0.572(7) 1 d D . P A 1
F2 F 1.110(2) 0.1262(16) 0.9526(12) 0.145(2) Uani 0.428(7) 1 d D . P A 2
F6 F 1.1435(19) 0.0500(16) 0.8152(13) 0.145(2) Uani 0.428(7) 1 d D . P A 2
F1 F 1.0382(16) 0.0479(13) 0.8852(10) 0.145(2) Uani 0.428(7) 1 d D . P A 2
F8 F 0.334(6) 0.655(7) 1.062(3) 0.21(3) Uani 0.35(3) 1 d D . P B 2
F12 F 0.169(2) 0.719(5) 0.938(2) 0.17(2) Uani 0.35(3) 1 d D . P B 2
F10 F 0.285(3) 0.8528(19) 1.017(3) 0.111(8) Uani 0.35(3) 1 d D . P B 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
O1 C9 1.191(7) . ?
N2 N1 1.449(6) . ?
N2 C9 1.381(7) . ?
N2 C22 1.411(6) . ?
N1 C5 1.426(7) . ?
N1 C8 1.536(7) . ?
C9 C8 1.540(7) . ?
C16 C17 1.389(7) . ?
C16 C8 1.511(7) . ?
C16 C21 1.366(7) . ?
C22 C27 1.388(8) . ?
C22 C23 1.385(8) . ?
C5 C4 1.378(7) . ?
C5 C6 1.368(7) . ?
C25 C24 1.367(9) . ?
C25 C26 1.385(9) . ?
C25 C28 1.487(8) . ?
C1 C2 1.430(11) . ?
C1 F5 1.295(17) . ?
C1 F4 1.426(16) . ?
C1 F3 1.305(15) . ?
C18 H18 0.9300 . ?
C18 C17 1.379(9) . ?
C18 C19 1.378(10) . ?
C27 H27 0.9300 . ?
C27 C26 1.385(8) . ?
C2 C3 1.366(8) . ?
C2 C7 1.389(8) . ?
C23 H23 0.9300 . ?
C23 C24 1.378(8) . ?
C10 C8 1.512(7) . ?
C10 C11 1.366(9) . ?
C10 C15 1.380(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.377(8) . ?
F5 F4 1.563(17) . ?
C17 H17 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.382(9) . ?
C3 H3 0.9300 . ?
C24 H24 0.9300 . ?
F4 F3 1.571(17) . ?
C26 H26 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.376(9) . ?
C28 F7 1.331(13) . ?
C28 F11 1.281(14) . ?
C28 F9 1.280(12) . ?
C28 F8 1.265(19) . ?
C28 F12 1.298(19) . ?
C28 F10 1.303(17) . ?
C20 H20 0.9300 . ?
C20 C19 1.338(10) . ?
C19 H19 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.387(10) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(14) . ?
C15 H15 0.9300 . ?
C15 C14 1.394(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(15) . ?
C14 H14 0.9300 . ?
F2 F1 1.31(2) . ?
F6 F1 1.47(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
C9 N2 N1 94.5(3) . . ?
C9 N2 C22 128.4(4) . . ?
C22 N2 N1 123.5(4) . . ?
N2 N1 C8 88.9(4) . . ?
C5 N1 N2 115.2(4) . . ?
C5 N1 C8 119.8(4) . . ?
O1 C9 N2 132.2(5) . . ?
O1 C9 C8 136.4(5) . . ?
N2 C9 C8 91.3(4) . . ?
C17 C16 C8 120.9(4) . . ?
C21 C16 C17 117.9(5) . . ?
C21 C16 C8 121.2(4) . . ?
C27 C22 N2 120.4(5) . . ?
C23 C22 N2 119.0(5) . . ?
C23 C22 C27 120.7(4) . . ?
C4 C5 N1 122.9(5) . . ?
C6 C5 N1 118.1(4) . . ?
C6 C5 C4 118.8(5) . . ?
C24 C25 C26 119.8(5) . . ?
C24 C25 C28 120.1(6) . . ?
C26 C25 C28 120.1(6) . . ?
F5 C1 C2 118.3(10) . . ?
F5 C1 F4 69.9(9) . . ?
F5 C1 F3 117.4(10) . . ?
F4 C1 C2 111.8(10) . . ?
F3 C1 C2 120.4(10) . . ?
F3 C1 F4 70.1(9) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C19 C18 C17 119.8(6) . . ?
C22 C27 H27 120.4 . . ?
C26 C27 C22 119.2(5) . . ?
C26 C27 H27 120.4 . . ?
C3 C2 C1 120.4(7) . . ?
C3 C2 C7 119.1(6) . . ?
C7 C2 C1 120.4(7) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 C22 118.9(6) . . ?
C24 C23 H23 120.6 . . ?
C11 C10 C8 122.6(5) . . ?
C11 C10 C15 119.4(6) . . ?
C15 C10 C8 118.0(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.2 . . ?
C1 F5 F4 59.0(9) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.7(5) . . ?
C18 C17 H17 119.6 . . ?
N1 C8 C9 85.0(3) . . ?
C16 C8 N1 117.6(4) . . ?
C16 C8 C9 113.0(4) . . ?
C16 C8 C10 114.9(4) . . ?
C10 C8 N1 111.0(4) . . ?
C10 C8 C9 111.6(4) . . ?
C16 C21 H21 119.6 . . ?
C16 C21 C20 120.9(5) . . ?
C20 C21 H21 119.6 . . ?
C2 C3 C4 121.6(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C25 C24 C23 121.3(6) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C1 F4 F5 51.1(8) . . ?
C1 F4 F3 51.3(7) . . ?
F5 F4 F3 90.2(9) . . ?
C25 C26 C27 120.1(6) . . ?
C25 C26 H26 119.9 . . ?
C27 C26 H26 119.9 . . ?
C5 C6 H6 118.9 . . ?
C5 C6 C7 122.1(5) . . ?
C7 C6 H6 118.9 . . ?
F7 C28 C25 114.1(8) . . ?
F11 C28 C25 113.2(9) . . ?
F11 C28 F7 101.2(11) . . ?
F9 C28 C25 114.5(8) . . ?
F9 C28 F7 105.0(14) . . ?
F9 C28 F11 107.7(16) . . ?
F8 C28 C25 111.2(13) . . ?
F8 C28 F12 121(3) . . ?
F8 C28 F10 104(3) . . ?
F12 C28 C25 112.7(16) . . ?
F12 C28 F10 95.6(18) . . ?
F10 C28 C25 110.5(10) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 C21 121.0(6) . . ?
C19 C20 H20 119.5 . . ?
C6 C7 C2 118.7(6) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.6(6) . . ?
C20 C19 H19 120.2 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(8) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(8) . . ?
C13 C12 H12 119.8 . . ?
C10 C15 H15 119.5 . . ?
C10 C15 C14 120.9(8) . . ?
C14 C15 H15 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.0(6) . . ?
C14 C13 H13 119.5 . . ?
C15 C14 H14 120.8 . . ?
C13 C14 C15 118.5(9) . . ?
C13 C14 H14 120.8 . . ?
C1 F3 F4 58.6(8) . . ?
F2 F1 F6 99.5(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C8 N1 -172.6(7) . . . . ?
O1 C9 C8 C16 69.4(8) . . . . ?
O1 C9 C8 C10 -62.0(9) . . . . ?
N2 N1 C5 C4 7.8(7) . . . . ?
N2 N1 C5 C6 -176.7(5) . . . . ?
N2 N1 C8 C9 -3.9(3) . . . . ?
N2 N1 C8 C16 109.5(5) . . . . ?
N2 N1 C8 C10 -115.1(4) . . . . ?
N2 C9 C8 N1 4.1(3) . . . . ?
N2 C9 C8 C16 -113.9(4) . . . . ?
N2 C9 C8 C10 114.7(5) . . . . ?
N2 C22 C27 C26 179.5(5) . . . . ?
N2 C22 C23 C24 179.8(5) . . . . ?
N1 N2 C9 O1 172.6(6) . . . . ?
N1 N2 C9 C8 -4.3(4) . . . . ?
N1 N2 C22 C27 10.9(7) . . . . ?
N1 N2 C22 C23 -170.7(5) . . . . ?
N1 C5 C4 C3 173.1(5) . . . . ?
N1 C5 C6 C7 -174.9(7) . . . . ?
C9 N2 N1 C5 127.0(5) . . . . ?
C9 N2 N1 C8 4.3(4) . . . . ?
C9 N2 C22 C27 141.0(6) . . . . ?
C9 N2 C22 C23 -40.5(7) . . . . ?
C16 C21 C20 C19 2.7(12) . . . . ?
C22 N2 N1 C5 -90.0(6) . . . . ?
C22 N2 N1 C8 147.4(4) . . . . ?
C22 N2 C9 O1 32.4(10) . . . . ?
C22 N2 C9 C8 -144.6(5) . . . . ?
C22 C27 C26 C25 -1.0(9) . . . . ?
C22 C23 C24 C25 2.6(9) . . . . ?
C5 N1 C8 C9 -122.6(5) . . . . ?
C5 N1 C8 C16 -9.2(6) . . . . ?
C5 N1 C8 C10 126.2(5) . . . . ?
C5 C4 C3 C2 0.9(9) . . . . ?
C5 C6 C7 C2 2.3(12) . . . . ?
C1 C2 C3 C4 179.3(8) . . . . ?
C1 C2 C7 C6 179.2(9) . . . . ?
C1 F5 F4 F3 36.3(8) . . . . ?
C27 C22 C23 C24 -1.8(8) . . . . ?
C2 C1 F5 F4 104.6(12) . . . . ?
C2 C1 F4 F5 -113.5(11) . . . . ?
C2 C1 F4 F3 115.8(12) . . . . ?
C2 C1 F3 F4 -104.2(13) . . . . ?
C23 C22 C27 C26 1.0(8) . . . . ?
C10 C11 C12 C13 -2.4(11) . . . . ?
C10 C15 C14 C13 0.0(13) . . . . ?
C4 C5 C6 C7 0.7(11) . . . . ?
F5 C1 C2 C3 -158.5(11) . . . . ?
F5 C1 C2 C7 18.6(16) . . . . ?
F5 C1 F4 F3 -130.7(10) . . . . ?
F5 C1 F3 F4 53.3(13) . . . . ?
F5 F4 F3 C1 -36.1(8) . . . . ?
C17 C16 C8 N1 105.5(6) . . . . ?
C17 C16 C8 C9 -157.8(5) . . . . ?
C17 C16 C8 C10 -28.1(7) . . . . ?
C17 C16 C21 C20 0.1(10) . . . . ?
C17 C18 C19 C20 1.5(11) . . . . ?
C8 N1 C5 C4 112.0(6) . . . . ?
C8 N1 C5 C6 -72.6(7) . . . . ?
C8 C16 C17 C18 176.9(6) . . . . ?
C8 C16 C21 C20 -178.8(6) . . . . ?
C8 C10 C11 C12 179.0(6) . . . . ?
C8 C10 C15 C14 -178.0(7) . . . . ?
C21 C16 C17 C18 -2.0(9) . . . . ?
C21 C16 C8 N1 -75.5(7) . . . . ?
C21 C16 C8 C9 21.1(7) . . . . ?
C21 C16 C8 C10 150.8(5) . . . . ?
C21 C20 C19 C18 -3.5(12) . . . . ?
C3 C2 C7 C6 -3.7(11) . . . . ?
C24 C25 C26 C27 1.7(9) . . . . ?
C24 C25 C28 F7 -172.1(11) . . . . ?
C24 C25 C28 F11 72.8(16) . . . . ?
C24 C25 C28 F9 -51(2) . . . . ?
C24 C25 C28 F8 -116(5) . . . . ?
C24 C25 C28 F12 105(2) . . . . ?
C24 C25 C28 F10 -1(2) . . . . ?
F4 C1 C2 C3 -80.3(11) . . . . ?
F4 C1 C2 C7 96.8(11) . . . . ?
C26 C25 C24 C23 -2.5(9) . . . . ?
C26 C25 C28 F7 9.4(14) . . . . ?
C26 C25 C28 F11 -105.6(15) . . . . ?
C26 C25 C28 F9 130(2) . . . . ?
C26 C25 C28 F8 65(5) . . . . ?
C26 C25 C28 F12 -74(2) . . . . ?
C26 C25 C28 F10 -179(2) . . . . ?
C6 C5 C4 C3 -2.3(9) . . . . ?
C28 C25 C24 C23 179.0(6) . . . . ?
C28 C25 C26 C27 -179.8(6) . . . . ?
C7 C2 C3 C4 2.2(10) . . . . ?
C19 C18 C17 C16 1.2(9) . . . . ?
C11 C10 C8 N1 -16.0(7) . . . . ?
C11 C10 C8 C9 -109.0(6) . . . . ?
C11 C10 C8 C16 120.6(6) . . . . ?
C11 C10 C15 C14 -0.1(11) . . . . ?
C11 C12 C13 C14 2.3(13) . . . . ?
C12 C13 C14 C15 -1.1(14) . . . . ?
C15 C10 C8 N1 161.8(5) . . . . ?
C15 C10 C8 C9 68.8(7) . . . . ?
C15 C10 C8 C16 -61.6(7) . . . . ?
C15 C10 C11 C12 1.3(10) . . . . ?
F3 C1 C2 C3 -1.3(17) . . . . ?
F3 C1 C2 C7 175.8(12) . . . . ?
F3 C1 F5 F4 -53.3(13) . . . . ?
F3 C1 F4 F5 130.7(10) . . . . ?

_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.732
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.4(4)
2 0.6(4)

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

data_1a-abl-p-me_auto
_database_code_depnum_ccdc_archive 'CCDC 2468261'
loop_
_audit_author_name
_audit_author_address
'Vijay Kumar Das'
;Banaras Hindu University
India
;
_audit_update_record             
;
2025-06-30 deposited with the CCDC.	2025-09-11 downloaded from the CCDC.
;
_audit_creation_date             2025-06-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 N2 O'
_chemical_formula_sum            'C28 H24 N2 O'
_chemical_formula_weight         404.49
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   14.6236(2)
_cell_length_b                   10.04030(10)
_cell_length_c                   15.0628(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.4030(10)
_cell_angle_gamma                90
_cell_volume                     2209.66(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13364
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.9520
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.90a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             856
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18779
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.093
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -18.00   0.50    0.42    --  -40.83 -64.00 164.00  180
  2  ω    -64.00  27.00   0.50    0.42    --  -40.83  64.00 -59.00  182
  3  ω    -26.00  64.00   0.50    0.42    --   40.83 -64.00 164.00  180
  4  ω     18.00 108.00   0.50    0.42    --   40.83  64.00 -59.00  180
  5  ω    -76.00 -15.00   0.50    1.68    --  -82.50  64.00 -59.00  122
  6  ω     73.00 164.00   0.50    1.68    --   96.04  64.00 -59.00  182
  7  ω     29.00  76.00   0.50    1.68    --   96.04 -64.00 164.00   94
  8  ω    -24.00  35.00   0.50    0.42    --  -40.83  11.00  30.00  118
  9  ω   -109.00 -28.00   0.50    0.42    --  -40.83 -32.00  60.00  162
 10  ω    -28.00  31.00   0.50    0.42    --  -40.83  21.00 -90.00  118
 11  ω    -37.00  27.00   0.50    0.42    --  -40.83  32.00  60.00  128
 12  ω     18.00  78.00   0.50    0.42    --   40.83-104.00  30.00  120
 13  ω     18.00  78.00   0.50    0.42    --   40.83-104.00   0.00  120
 14  ω    -47.00 -15.00   0.50    1.68    --  -82.50  42.00 120.00   64
 15  ω    -47.00 -15.00   0.50    1.68    --  -82.50  42.00-180.00   64
 16  ω   -150.00 -59.00   0.50    1.68    --  -82.50 -64.00 164.00  182
 17  ω     99.00 160.00   0.50    1.68    --   96.04 117.00   0.00  122
 18  ω     28.00  68.00   0.50    1.68    --   96.04 -59.00  30.00   80
 19  ω    105.00 170.00   0.50    1.68    --   96.04  96.00-150.00  130
 20  ω     27.00 105.00   0.50    1.68    --   96.04 -77.00 -30.00  156
 21  ω     32.00 110.00   0.50    1.68    --   96.04-117.00 150.00  156
 22  ω     29.00  57.00   0.50    1.68    --   96.04 -50.00 120.00   56
 23  ω     79.00 162.00   0.50    1.68    --   96.04  42.00 -90.00  166
 24  ω     28.00  68.00   0.50    1.68    --   96.04 -59.00 120.00   80
 25  ω     72.00 164.00   0.50    1.68    --   96.04  68.00 -90.00  184
 26  ω     28.00  68.00   0.50    1.68    --   96.04 -59.00-180.00   80
 27  ω     29.00  57.00   0.50    1.68    --   96.04 -50.00   0.00   56
 28  ω     29.00  57.00   0.50    1.68    --   96.04 -50.00-120.00   56
 29  ω     29.00  57.00   0.50    1.68    --   96.04 -50.00  60.00   56
 30  ω     29.00  57.00   0.50    1.68    --   96.04 -50.00 150.00   56
 31  ω     23.00 106.00   0.50    1.68    --   96.04 -96.00 150.00  166
 32  ω     27.00 105.00   0.50    1.68    --   96.04 -77.00-120.00  156
 33  ω     81.00 166.00   0.50    1.68    --   96.04  25.00  60.00  170
 34  ω   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00  30.00  190
 35  ω   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00 -30.00  190
 36  ω   -109.00 -14.00   0.50    0.42    --  -40.83 -77.00  90.00  190
 37  ω   -109.00 -28.00   0.50    0.42    --  -40.83 -32.00-150.00  162
 38  ω     14.00  91.00   0.50    0.42    --   40.83  77.00-180.00  154
 39  ω     14.00 110.00   0.50    0.42    --   40.83  77.00-120.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0539290000
_diffrn_orient_matrix_UB_12      0.0686883000
_diffrn_orient_matrix_UB_13      0.0772247000
_diffrn_orient_matrix_UB_21      0.0454837000
_diffrn_orient_matrix_UB_22      0.0927185000
_diffrn_orient_matrix_UB_23      -0.0666473000
_diffrn_orient_matrix_UB_31      -0.0783566000
_diffrn_orient_matrix_UB_32      0.1011189000
_diffrn_orient_matrix_UB_33      0.0086965000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3402
_reflns_number_total             4005
_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 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.90a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4005
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0460
_refine_ls_restrained_S_all      1.172
_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)+(0.0467P)²+0.7001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1312
_refine_ls_wR_factor_ref         0.1355
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C10(H10), C27(H27), C17(H17), C19(H19), C23(H23),
 C26(H26), C24(H24), C14(H14), C8(H8), C11(H11), C4(H4), C12(H12), C7(H7),
 C13(H13), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75056(9) 0.31186(13) 0.50423(9) 0.0550(4) Uani 1 1 d . . . . .
N2 N 0.71756(10) 0.63504(14) 0.51328(9) 0.0428(3) Uani 1 1 d . . . . .
N1 N 0.69253(10) 0.51947(14) 0.45823(9) 0.0446(4) Uani 1 1 d . . . . .
C9 C 0.70663(11) 0.52555(18) 0.66840(11) 0.0434(4) Uani 1 1 d . . . . .
C15 C 0.64067(11) 0.71423(17) 0.53713(11) 0.0419(4) Uani 1 1 d . . . . .
C1 C 0.73445(12) 0.42885(18) 0.51325(11) 0.0432(4) Uani 1 1 d . . . . .
C2 C 0.75759(11) 0.53588(17) 0.58343(11) 0.0418(4) Uani 1 1 d . . . . .
C22 C 0.68047(11) 0.52221(18) 0.36440(11) 0.0424(4) Uani 1 1 d . . . . .
C16 C 0.55202(12) 0.69121(19) 0.50587(12) 0.0494(4) Uani 1 1 d . . . . .
H16 H 0.539004 0.619092 0.468714 0.059 Uiso 1 1 calc R U . . .
C20 C 0.65859(13) 0.82342(19) 0.59167(12) 0.0491(4) Uani 1 1 d . . . . .
H20 H 0.718332 0.841802 0.611548 0.059 Uiso 1 1 calc R U . . .
C3 C 0.86047(12) 0.54974(19) 0.59757(11) 0.0471(4) Uani 1 1 d . . . . .
C10 C 0.73339(13) 0.6000(2) 0.74246(12) 0.0528(5) Uani 1 1 d . . . . .
H10 H 0.784265 0.655375 0.740497 0.063 Uiso 1 1 calc R U . . .
C27 C 0.68913(14) 0.63844(19) 0.31690(12) 0.0541(5) Uani 1 1 d . . . . .
H27 H 0.701111 0.718470 0.346216 0.065 Uiso 1 1 calc R U . . .
C18 C 0.49837(13) 0.8828(2) 0.58637(12) 0.0512(5) Uani 1 1 d . . . . .
C17 C 0.48257(13) 0.7757(2) 0.52997(13) 0.0542(5) Uani 1 1 d . . . . .
H17 H 0.423330 0.760075 0.507527 0.065 Uiso 1 1 calc R U . . .
C25 C 0.66168(13) 0.5182(2) 0.17925(12) 0.0507(5) Uani 1 1 d . . . . .
C19 C 0.58807(14) 0.9047(2) 0.61644(12) 0.0540(5) Uani 1 1 d . . . . .
H19 H 0.600978 0.976024 0.654308 0.065 Uiso 1 1 calc R U . . .
C23 C 0.65991(14) 0.4047(2) 0.32019(12) 0.0549(5) Uani 1 1 d . . . . .
H23 H 0.652019 0.326427 0.351985 0.066 Uiso 1 1 calc R U . . .
C26 C 0.67982(15) 0.6349(2) 0.22497(13) 0.0598(5) Uani 1 1 d . . . . .
H26 H 0.685972 0.713586 0.193169 0.072 Uiso 1 1 calc R U . . .
C24 C 0.65115(14) 0.4040(2) 0.22875(12) 0.0559(5) Uani 1 1 d . . . . .
H24 H 0.637737 0.324341 0.199569 0.067 Uiso 1 1 calc R U . . .
C14 C 0.63100(13) 0.4440(2) 0.67356(13) 0.0605(5) Uani 1 1 d . . . . .
H14 H 0.612146 0.392921 0.624636 0.073 Uiso 1 1 calc R U . . .
C8 C 0.90680(14) 0.4498(2) 0.64372(14) 0.0640(6) Uani 1 1 d . . . . .
H8 H 0.874430 0.379062 0.666951 0.077 Uiso 1 1 calc R U . . .
C11 C 0.68496(16) 0.5927(2) 0.81941(13) 0.0659(6) Uani 1 1 d . . . . .
H11 H 0.703413 0.643120 0.868763 0.079 Uiso 1 1 calc R U . . .
C4 C 0.90936(15) 0.6533(2) 0.56396(16) 0.0688(6) Uani 1 1 d . . . . .
H4 H 0.879336 0.721483 0.532718 0.083 Uiso 1 1 calc R U . . .
C21 C 0.42117(15) 0.9717(2) 0.61293(15) 0.0696(6) Uani 1 1 d . . . . .
H21A H 0.383754 0.994414 0.561250 0.104 Uiso 1 1 calc R U . . .
H21B H 0.445812 1.051481 0.639680 0.104 Uiso 1 1 calc R U . . .
H21C H 0.384731 0.925856 0.654791 0.104 Uiso 1 1 calc R U . . .
C28 C 0.65297(17) 0.5135(3) 0.07899(13) 0.0714(6) Uani 1 1 d . . . . .
H28A H 0.590590 0.495081 0.060627 0.107 Uiso 1 1 calc R U . . .
H28B H 0.691850 0.444609 0.057496 0.107 Uiso 1 1 calc R U . . .
H28C H 0.670933 0.597735 0.055156 0.107 Uiso 1 1 calc R U . . .
C12 C 0.61022(17) 0.5117(3) 0.82300(15) 0.0754(7) Uani 1 1 d . . . . .
H12 H 0.577822 0.507126 0.874742 0.090 Uiso 1 1 calc R U . . .
C7 C 1.00081(16) 0.4544(3) 0.65552(18) 0.0820(8) Uani 1 1 d . . . . .
H7 H 1.031419 0.386542 0.686502 0.098 Uiso 1 1 calc R U . . .
C13 C 0.58294(16) 0.4373(3) 0.75059(16) 0.0784(7) Uani 1 1 d . . . . .
H13 H 0.532028 0.382108 0.753145 0.094 Uiso 1 1 calc R U . . .
C5 C 1.00412(18) 0.6561(3) 0.5768(2) 0.0916(9) Uani 1 1 d . . . . .
H5 H 1.037192 0.726429 0.554025 0.110 Uiso 1 1 calc R U . . .
C6 C 1.04895(16) 0.5572(4) 0.62226(19) 0.0891(9) Uani 1 1 d . . . . .
H6 H 1.112302 0.559901 0.630520 0.107 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.207(2) . ?
N2 N1 1.4638(19) . ?
N2 C15 1.435(2) . ?
N2 C2 1.549(2) . ?
N1 C1 1.359(2) . ?
N1 C22 1.417(2) . ?
C9 C2 1.511(2) . ?
C9 C10 1.386(3) . ?
C9 C14 1.381(3) . ?
C15 C16 1.380(2) . ?
C15 C20 1.388(2) . ?
C1 C2 1.535(2) . ?
C2 C3 1.517(2) . ?
C22 C27 1.377(3) . ?
C22 C23 1.382(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.384(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(3) . ?
C3 C8 1.382(3) . ?
C3 C4 1.371(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.386(3) . ?
C18 C17 1.384(3) . ?
C18 C19 1.387(3) . ?
C18 C21 1.506(3) . ?
C17 H17 0.9300 . ?
C25 C26 1.380(3) . ?
C25 C24 1.379(3) . ?
C25 C28 1.511(3) . ?
C19 H19 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.378(3) . ?
C26 H26 0.9300 . ?
C24 H24 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.383(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.380(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.365(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.391(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C13 1.368(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.357(4) . ?
C13 H13 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.359(4) . ?
C6 H6 0.9300 . ?

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
N1 N2 C2 87.44(11) . . ?
C15 N2 N1 113.64(13) . . ?
C15 N2 C2 117.59(13) . . ?
C1 N1 N2 95.14(12) . . ?
C1 N1 C22 130.92(15) . . ?
C22 N1 N2 124.56(14) . . ?
C10 C9 C2 120.80(16) . . ?
C14 C9 C2 120.86(16) . . ?
C14 C9 C10 118.33(17) . . ?
C16 C15 N2 123.81(16) . . ?
C16 C15 C20 119.04(17) . . ?
C20 C15 N2 117.08(15) . . ?
O1 C1 N1 131.92(16) . . ?
O1 C1 C2 136.08(16) . . ?
N1 C1 C2 91.84(14) . . ?
C9 C2 N2 115.86(14) . . ?
C9 C2 C1 115.64(14) . . ?
C9 C2 C3 114.13(14) . . ?
C1 C2 N2 85.07(12) . . ?
C3 C2 N2 112.40(14) . . ?
C3 C2 C1 110.46(14) . . ?
C27 C22 N1 121.61(16) . . ?
C27 C22 C23 119.73(16) . . ?
C23 C22 N1 118.66(16) . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.81(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C20 H20 119.9 . . ?
C19 C20 C15 120.18(17) . . ?
C19 C20 H20 119.9 . . ?
C8 C3 C2 117.80(17) . . ?
C4 C3 C2 123.18(18) . . ?
C4 C3 C8 118.97(19) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C22 C27 H27 120.3 . . ?
C22 C27 C26 119.34(18) . . ?
C26 C27 H27 120.3 . . ?
C17 C18 C19 117.04(17) . . ?
C17 C18 C21 121.04(19) . . ?
C19 C18 C21 121.92(19) . . ?
C16 C17 C18 122.15(18) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C26 C25 C28 122.13(19) . . ?
C24 C25 C26 117.36(17) . . ?
C24 C25 C28 120.51(18) . . ?
C20 C19 C18 121.73(18) . . ?
C20 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.67(18) . . ?
C24 C23 H23 120.2 . . ?
C27 C26 H26 119.0 . . ?
C25 C26 C27 121.94(18) . . ?
C25 C26 H26 119.0 . . ?
C25 C24 H24 119.0 . . ?
C23 C24 C25 121.91(18) . . ?
C23 C24 H24 119.0 . . ?
C9 C14 H14 119.6 . . ?
C9 C14 C13 120.8(2) . . ?
C13 C14 H14 119.6 . . ?
C3 C8 H8 119.8 . . ?
C7 C8 C3 120.4(2) . . ?
C7 C8 H8 119.8 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C25 C28 H28A 109.5 . . ?
C25 C28 H28B 109.5 . . ?
C25 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(2) . . ?
C13 C12 H12 120.0 . . ?
C8 C7 H7 119.7 . . ?
C6 C7 C8 120.5(3) . . ?
C6 C7 H7 119.7 . . ?
C14 C13 H13 120.0 . . ?
C12 C13 C14 120.1(2) . . ?
C12 C13 H13 120.0 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 119.7(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 170.1(2) . . . . ?
O1 C1 C2 C9 -73.5(3) . . . . ?
O1 C1 C2 C3 58.0(3) . . . . ?
N2 N1 C1 O1 -170.1(2) . . . . ?
N2 N1 C1 C2 5.71(13) . . . . ?
N2 N1 C22 C27 -2.0(3) . . . . ?
N2 N1 C22 C23 177.77(16) . . . . ?
N2 C15 C16 C17 -177.67(16) . . . . ?
N2 C15 C20 C19 179.31(16) . . . . ?
N2 C2 C3 C8 -166.61(16) . . . . ?
N2 C2 C3 C4 10.8(2) . . . . ?
N1 N2 C15 C16 -5.0(2) . . . . ?
N1 N2 C15 C20 178.05(14) . . . . ?
N1 N2 C2 C9 -111.15(15) . . . . ?
N1 N2 C2 C1 5.01(11) . . . . ?
N1 N2 C2 C3 115.13(14) . . . . ?
N1 C1 C2 N2 -5.40(12) . . . . ?
N1 C1 C2 C9 110.98(16) . . . . ?
N1 C1 C2 C3 -117.48(15) . . . . ?
N1 C22 C27 C26 177.76(18) . . . . ?
N1 C22 C23 C24 -177.67(18) . . . . ?
C9 C2 C3 C8 58.8(2) . . . . ?
C9 C2 C3 C4 -123.7(2) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C9 C14 C13 C12 -0.2(4) . . . . ?
C15 N2 N1 C1 -124.77(14) . . . . ?
C15 N2 N1 C22 85.84(19) . . . . ?
C15 N2 C2 C9 4.3(2) . . . . ?
C15 N2 C2 C1 120.45(15) . . . . ?
C15 N2 C2 C3 -129.43(15) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C15 C20 C19 C18 -1.7(3) . . . . ?
C1 N1 C22 C27 -139.8(2) . . . . ?
C1 N1 C22 C23 39.9(3) . . . . ?
C1 C2 C3 C8 -73.5(2) . . . . ?
C1 C2 C3 C4 103.9(2) . . . . ?
C2 N2 N1 C1 -5.66(13) . . . . ?
C2 N2 N1 C22 -155.05(16) . . . . ?
C2 N2 C15 C16 -104.97(19) . . . . ?
C2 N2 C15 C20 78.05(19) . . . . ?
C2 C9 C10 C11 178.32(18) . . . . ?
C2 C9 C14 C13 -178.3(2) . . . . ?
C2 C3 C8 C7 177.40(19) . . . . ?
C2 C3 C4 C5 -177.4(2) . . . . ?
C22 N1 C1 O1 -23.8(3) . . . . ?
C22 N1 C1 C2 151.99(18) . . . . ?
C22 C27 C26 C25 0.3(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C16 C15 C20 C19 2.2(3) . . . . ?
C20 C15 C16 C17 -0.7(3) . . . . ?
C3 C8 C7 C6 0.2(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C10 C9 C2 N2 -94.82(19) . . . . ?
C10 C9 C2 C1 167.90(16) . . . . ?
C10 C9 C2 C3 38.1(2) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C27 C22 C23 C24 2.1(3) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C19 C18 C17 C16 1.7(3) . . . . ?
C23 C22 C27 C26 -2.0(3) . . . . ?
C26 C25 C24 C23 -1.2(3) . . . . ?
C24 C25 C26 C27 1.3(3) . . . . ?
C14 C9 C2 N2 83.7(2) . . . . ?
C14 C9 C2 C1 -13.6(2) . . . . ?
C14 C9 C2 C3 -143.37(18) . . . . ?
C14 C9 C10 C11 -0.2(3) . . . . ?
C8 C3 C4 C5 0.0(3) . . . . ?
C8 C7 C6 C5 -0.2(4) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C4 C3 C8 C7 -0.1(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C21 C18 C17 C16 -178.79(18) . . . . ?
C21 C18 C19 C20 -179.73(19) . . . . ?
C28 C25 C26 C27 -179.0(2) . . . . ?
C28 C25 C24 C23 179.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.039
_oxdiff_exptl_absorpt_empirical_full_min 0.753
