# Supplementary Information (SI) for RSC Advances.
# 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_mm4-034_1
_database_code_depnum_ccdc_archive 'CCDC 2491387'
loop_
_audit_author_name
_audit_author_address
'Akitaka Ito'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_audit_creation_date             2022-05-17
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1-methoxy-4-(4-nitrophenyl)naphthalene
_chemical_formula_moiety         'C17 H13 N O3'
_chemical_formula_sum            'C17 H13 N O3'
_chemical_formula_weight         279.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C68 H52 N4 O12 '
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/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                   10.0247(4)
_cell_length_b                   10.2858(3)
_cell_length_c                   13.4724(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.611(4)
_cell_angle_gamma                90
_cell_volume                     1300.25(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7148
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      29.5880
_cell_measurement_theta_min      2.2150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.123
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.2240
0 -1 -1 0.2181
1 2 -2 0.1721
1 -1 -1 0.2127
0 0 1 0.3226
1 -2 1 0.2702
-1 2 -1 0.2835
1 -1 -2 0.2282
-1 1 2 0.2349
2 -1 0 0.3208
-2 1 0 0.3454
1 0 -1 0.2133
2 1 -2 0.1849
-2 -1 2 0.1747
0 1 0 0.2221
0 -1 0 0.2596
1 2 1 0.2552
-1 -2 2 0.2217
1 1 -1 0.1483
-1 -1 1 0.1710
-1 -1 2 0.2144
1 0 1 0.3701
-1 0 -2 0.3400
0 -1 1 0.2521
0 -1 2 0.2818
-1 2 2 0.2174
-1 2 0 0.2660
0 0 -1 0.2715
-1 0 1 0.1936

_exptl_crystal_size_max          0.734
_exptl_crystal_size_mid          0.459
_exptl_crystal_size_min          0.319
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 1.0000 1.0000 -0.0183 -0.0805 0.0332
0.0000 -1.0000 -1.0000 0.0183 0.0805 -0.0332
1.0000 2.0000 -2.0000 -0.1056 -0.0822 -0.1162
1.0000 -1.0000 -1.0000 -0.0499 0.0903 -0.0018
0.0000 0.0000 1.0000 0.0002 -0.0172 0.0535
1.0000 -2.0000 1.0000 -0.0309 0.1191 0.1255
-1.0000 2.0000 -1.0000 0.0309 -0.1191 -0.1255
1.0000 -1.0000 -2.0000 -0.0501 0.1075 -0.0553
-1.0000 1.0000 2.0000 0.0501 -0.1075 0.0553
2.0000 -1.0000 -0.0000 -0.1178 0.0829 0.0831
-2.0000 1.0000 0.0000 0.1178 -0.0829 -0.0831
1.0000 -0.0000 -1.0000 -0.0684 0.0271 -0.0221
2.0000 1.0000 -2.0000 -0.1552 -0.0091 -0.0646
-2.0000 -1.0000 2.0000 0.1552 0.0091 0.0646
-0.0000 1.0000 0.0000 -0.0185 -0.0632 -0.0203
0.0000 -1.0000 -0.0000 0.0185 0.0632 0.0203
1.0000 2.0000 1.0000 -0.1049 -0.1339 0.0443
-1.0000 -2.0000 2.0000 0.1056 0.0822 0.1162
1.0000 1.0000 -1.0000 -0.0869 -0.0362 -0.0424
-1.0000 -1.0000 1.0000 0.0869 0.0362 0.0424
-1.0000 -1.0000 2.0000 0.0871 0.0189 0.0959
1.0000 0.0000 1.0000 -0.0679 -0.0074 0.0849
-1.0000 -0.0000 -2.0000 0.0677 0.0246 -0.1384
0.0000 -1.0000 1.0000 0.0187 0.0460 0.0738
0.0000 -1.0000 2.0000 0.0190 0.0288 0.1273
-1.0000 2.0000 2.0000 0.0316 -0.1707 0.0350
-1.0000 2.0000 0.0000 0.0311 -0.1363 -0.0720
-0.0000 -0.0000 -1.0000 -0.0002 0.0172 -0.0535
-1.0000 0.0000 1.0000 0.0684 -0.0271 0.0221

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.203
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  58.00   0.50    1.65    --   12.72-101.00-158.00  142
  2  ω    -21.00   5.00   0.50    1.65    --   12.72 101.00 -53.00   52
  3  ω    -14.00  88.00   0.50    1.65    --   12.72  57.00  30.00  204
  4  ω     42.00  94.00   0.50    1.65    --   12.72 178.00 150.00  104
  5  ω     44.00  69.00   0.50    1.65    --   12.72 178.00-150.00   50
  6  ω    -17.00   8.00   0.50    1.65    --  -13.42-101.00-158.00   50
  7  ω    -27.00  -2.00   0.50    1.65    --  -13.42 101.00 -53.00   50
  8  ω    -66.00 -41.00   0.50    1.65    --  -13.42-178.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0681235000
_diffrn_orient_matrix_UB_12      -0.0184939000
_diffrn_orient_matrix_UB_13      0.0002361000
_diffrn_orient_matrix_UB_21      0.0098205000
_diffrn_orient_matrix_UB_22      -0.0632320000
_diffrn_orient_matrix_UB_23      -0.0172312000
_diffrn_orient_matrix_UB_31      0.0313735000
_diffrn_orient_matrix_UB_32      -0.0203070000
_diffrn_orient_matrix_UB_33      0.0535046000
_diffrn_oxdiff_digest_frames     
;
01c22f3dd3224d024400f2a616d7b714ad00702ee83
;
_diffrn_oxdiff_digest_hkl        
;
0129a9ac78384245006b3550add580260baa8e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2398
_reflns_number_total             2654
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.229
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2654
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.3522P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0975
_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:
 C008(H008), C00B(H00B), C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K)
2.b Idealised Me refined as rotating group:
 C00L(H00A,H00E,H00L)
;
_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
O001 O 0.78307(8) 0.55016(8) 0.66530(6) 0.0183(2) Uani 1 1 d . . . . .
O002 O 0.42047(9) 0.69945(9) -0.16077(6) 0.0245(2) Uani 1 1 d . . . . .
O003 O 0.22980(8) 0.60282(8) -0.15742(6) 0.0222(2) Uani 1 1 d . . . . .
N004 N 0.34872(10) 0.65001(9) -0.11285(7) 0.0175(2) Uani 1 1 d . . . . .
C005 C 0.59901(11) 0.64109(10) 0.52120(9) 0.0147(2) Uani 1 1 d . . . . .
C006 C 0.40842(12) 0.64553(10) 0.00308(8) 0.0154(2) Uani 1 1 d . . . . .
C007 C 0.72759(11) 0.56681(11) 0.55797(8) 0.0155(2) Uani 1 1 d . . . . .
C008 C 0.40850(11) 0.74310(11) 0.37646(9) 0.0172(2) Uani 1 1 d . . . . .
H008 H 0.363130 0.760942 0.303032 0.021 Uiso 1 1 calc R . . . .
C009 C 0.53212(11) 0.66374(10) 0.41047(9) 0.0148(2) Uani 1 1 d . . . . .
C00A C 0.59397(11) 0.61009(10) 0.33829(9) 0.0154(2) Uani 1 1 d . . . . .
C00B C 0.53913(12) 0.69526(11) 0.59313(9) 0.0172(2) Uani 1 1 d . . . . .
H00B H 0.583081 0.679389 0.666996 0.021 Uiso 1 1 calc R . . . .
C00C C 0.60685(12) 0.67337(11) 0.16287(9) 0.0170(2) Uani 1 1 d . . . . .
H00C H 0.703032 0.698664 0.198653 0.020 Uiso 1 1 calc R . . . .
C00D C 0.38408(12) 0.59125(11) 0.16770(9) 0.0172(2) Uani 1 1 d . . . . .
H00D H 0.327791 0.560469 0.206655 0.021 Uiso 1 1 calc R . . . .
C00E C 0.52621(12) 0.62647(10) 0.22165(9) 0.0156(2) Uani 1 1 d . . . . .
C00F C 0.32434(12) 0.60070(10) 0.05816(9) 0.0168(2) Uani 1 1 d . . . . .
H00F H 0.227826 0.576911 0.021762 0.020 Uiso 1 1 calc R . . . .
C00G C 0.78728(12) 0.51967(11) 0.48809(9) 0.0172(2) Uani 1 1 d . . . . .
H00G H 0.874130 0.472327 0.513428 0.021 Uiso 1 1 calc R . . . .
C00H C 0.71934(11) 0.54166(11) 0.37827(9) 0.0172(2) Uani 1 1 d . . . . .
H00H H 0.761587 0.508124 0.330590 0.021 Uiso 1 1 calc R . . . .
C00I C 0.41887(12) 0.76998(12) 0.55697(9) 0.0198(3) Uani 1 1 d . . . . .
H00I H 0.379383 0.805451 0.605643 0.024 Uiso 1 1 calc R . . . .
C00J C 0.54870(12) 0.68343(11) 0.05357(9) 0.0169(2) Uani 1 1 d . . . . .
H00J H 0.603674 0.715581 0.014082 0.020 Uiso 1 1 calc R . . . .
C00K C 0.35341(12) 0.79446(11) 0.44760(9) 0.0192(3) Uani 1 1 d . . . . .
H00K H 0.270295 0.847068 0.422965 0.023 Uiso 1 1 calc R . . . .
C00L C 0.91670(12) 0.48368(13) 0.70722(9) 0.0240(3) Uani 1 1 d . . . . .
H00A H 0.906081 0.394906 0.679086 0.036 Uiso 1 1 calc GR . . . .
H00E H 0.947219 0.480668 0.784741 0.036 Uiso 1 1 calc GR . . . .
H00L H 0.988316 0.529957 0.686534 0.036 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
O001 C007 1.3650(13) . ?
O001 C00L 1.4312(14) . ?
O002 N004 1.2327(13) . ?
O003 N004 1.2302(12) . ?
N004 C006 1.4635(14) . ?
C005 C007 1.4287(15) . ?
C005 C009 1.4231(15) . ?
C005 C00B 1.4210(15) . ?
C006 C00F 1.3835(16) . ?
C006 C00J 1.3852(16) . ?
C007 C00G 1.3696(16) . ?
C008 C009 1.4186(15) . ?
C008 C00K 1.3693(16) . ?
C009 C00A 1.4349(15) . ?
C00A C00E 1.4858(15) . ?
C00A C00H 1.3742(16) . ?
C00B C00I 1.3668(16) . ?
C00C C00E 1.4015(15) . ?
C00C C00J 1.3837(15) . ?
C00D C00E 1.4002(16) . ?
C00D C00F 1.3870(15) . ?
C00G C00H 1.4124(15) . ?
C00I C00K 1.4087(16) . ?

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
C007 O001 C00L 116.98(9) . . ?
O002 N004 C006 118.50(9) . . ?
O003 N004 O002 123.44(10) . . ?
O003 N004 C006 118.06(9) . . ?
C009 C005 C007 119.05(10) . . ?
C00B C005 C007 121.29(10) . . ?
C00B C005 C009 119.63(10) . . ?
C00F C006 N004 119.05(10) . . ?
C00F C006 C00J 122.36(10) . . ?
C00J C006 N004 118.57(10) . . ?
O001 C007 C005 114.57(9) . . ?
O001 C007 C00G 124.75(10) . . ?
C00G C007 C005 120.67(10) . . ?
C00K C008 C009 121.18(10) . . ?
C005 C009 C00A 119.40(10) . . ?
C008 C009 C005 117.93(10) . . ?
C008 C009 C00A 122.63(10) . . ?
C009 C00A C00E 121.83(10) . . ?
C00H C00A C009 119.02(10) . . ?
C00H C00A C00E 119.15(10) . . ?
C00I C00B C005 120.59(10) . . ?
C00J C00C C00E 121.09(10) . . ?
C00F C00D C00E 120.90(10) . . ?
C00C C00E C00A 119.79(10) . . ?
C00D C00E C00A 121.50(10) . . ?
C00D C00E C00C 118.67(10) . . ?
C006 C00F C00D 118.54(10) . . ?
C007 C00G C00H 119.81(10) . . ?
C00A C00H C00G 121.99(10) . . ?
C00B C00I C00K 120.06(10) . . ?
C00C C00J C006 118.43(10) . . ?
C008 C00K C00I 120.60(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 1.256
_oxdiff_exptl_absorpt_empirical_full_min 0.887
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: ethanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_mm4-084_1
_database_code_depnum_ccdc_archive 'CCDC 2491388'
loop_
_audit_author_name
_audit_author_address
'Akitaka Ito'
;Kochi University of Technology
Japan
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-11 downloaded from the CCDC.
;
_audit_creation_date             2022-07-21
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1-methoxy-4-phenylnaphthalene
_chemical_formula_moiety         'C17 H14 O'
_chemical_formula_sum            'C17 H14 O'
_chemical_formula_weight         234.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C17 H14 O1'
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'
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                   11.5001(5)
_cell_length_b                   17.6022(8)
_cell_length_c                   5.9565(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.087(5)
_cell_angle_gamma                90
_cell_volume                     1202.69(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3960
_cell_measurement_temperature    103.15
_cell_measurement_theta_max      29.8320
_cell_measurement_theta_min      2.1230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 0 0.0053
1 0 0 0.0078
1 1 0 0.0298
0 1 0 0.0430
1 1 1 0.1590
-1 -2 -1 0.1102
0 -1 0 0.0489
0 -1 1 0.1890
0 1 -1 0.1555

_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.013
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 -0.0001 -0.0000 0.0604 -0.0027 0.0132
1.0000 0.0001 0.0000 -0.0604 0.0027 -0.0132
1.0000 1.0001 0.0000 -0.0678 0.0166 0.0239
-0.0000 1.0000 -0.0000 -0.0075 0.0140 0.0371
1.0000 1.0001 1.0000 -0.0625 0.1286 -0.0171
-1.0000 -2.0001 -1.0000 0.0700 -0.1425 -0.0199
0.0000 -1.0000 0.0000 0.0075 -0.0140 -0.0371
0.0000 -1.0000 1.0000 0.0128 0.0980 -0.0781
-0.0000 1.0000 -1.0000 -0.0128 -0.0980 0.0781

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            8417
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.119
_diffrn_ambient_temperature      103.15
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  52.00   0.50   36.61    --   12.72  30.00  18.00  116
  2  ω     70.00  95.00   0.50   36.61    --   12.72  30.00  18.00   50
  3  ω     36.00  87.00   0.50   36.61    --   12.72  57.00  60.00  102
  4  ω    -13.00  31.00   0.50   36.61    --   12.72  57.00  60.00   88
  5  ω    -68.00  14.00   0.50   36.61    --   12.72 -30.00-141.00  164
  6  ω    -21.00  31.00   0.50   36.61    --  -13.34 -99.00 120.00  104
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0603839000
_diffrn_orient_matrix_UB_12      -0.0074544000
_diffrn_orient_matrix_UB_13      0.0052987000
_diffrn_orient_matrix_UB_21      0.0026913000
_diffrn_orient_matrix_UB_22      0.0139515000
_diffrn_orient_matrix_UB_23      0.1119084000
_diffrn_orient_matrix_UB_31      -0.0131745000
_diffrn_orient_matrix_UB_32      0.0370649000
_diffrn_orient_matrix_UB_33      -0.0410408000
_diffrn_oxdiff_digest_frames     
;
0190ffffa30f8b0d1cc4f2f90b91c799c6006248e8b
;
_diffrn_oxdiff_digest_hkl        
;
01dd7a33daaf0df94b754e0166e13a1c1af597
;
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1940
_reflns_number_total             2463
_reflns_odcompleteness_completeness 99.96
_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       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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         0.319
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0586
_refine_ls_restrained_S_all      1.090
_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)+(0.0607P)²+1.4642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1593
_refine_ls_wR_factor_ref         0.1672
_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:
 C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H)
2.b Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K)
;
_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
O001 O 0.96100(13) 0.64378(9) 0.5910(3) 0.0262(4) Uani 1 1 d . . . . .
C002 C 0.84195(18) 0.64428(12) 0.5546(4) 0.0199(5) Uani 1 1 d . . . . .
C003 C 0.67584(18) 0.60170(11) 0.3036(4) 0.0180(5) Uani 1 1 d . . . . .
C004 C 0.59914(18) 0.64053(11) 0.4447(4) 0.0181(5) Uani 1 1 d . . . . .
C005 C 0.46983(18) 0.64034(11) 0.3955(4) 0.0176(5) Uani 1 1 d . . . . .
C006 C 0.79830(18) 0.60250(12) 0.3613(4) 0.0191(5) Uani 1 1 d . . . . .
C007 C 0.63441(19) 0.55987(12) 0.1102(4) 0.0198(5) Uani 1 1 d . . . . .
H007 H 0.553071 0.558594 0.069175 0.024 Uiso 1 1 calc R . . . .
C008 C 0.41720(19) 0.67377(11) 0.2000(4) 0.0198(5) Uani 1 1 d . . . . .
H008 H 0.464301 0.694400 0.090291 0.024 Uiso 1 1 calc R . . . .
C009 C 0.64646(19) 0.67769(12) 0.6313(4) 0.0200(5) Uani 1 1 d . . . . .
H009 H 0.595546 0.702329 0.726840 0.024 Uiso 1 1 calc R . . . .
C00A C 0.2969(2) 0.67684(12) 0.1661(4) 0.0223(5) Uani 1 1 d . . . . .
H00A H 0.262038 0.700567 0.034765 0.027 Uiso 1 1 calc R . . . .
C00B C 0.87327(19) 0.56123(13) 0.2259(4) 0.0231(5) Uani 1 1 d . . . . .
H00B H 0.954858 0.560958 0.264580 0.028 Uiso 1 1 calc R . . . .
C00C C 0.39839(19) 0.60897(12) 0.5505(4) 0.0213(5) Uani 1 1 d . . . . .
H00C H 0.432688 0.585785 0.683169 0.026 Uiso 1 1 calc R . . . .
C00D C 0.76742(19) 0.68099(12) 0.6877(4) 0.0210(5) Uani 1 1 d . . . . .
H00D H 0.797026 0.708383 0.816846 0.025 Uiso 1 1 calc R . . . .
C00E C 0.22691(19) 0.64560(12) 0.3221(4) 0.0238(5) Uani 1 1 d . . . . .
H00E H 0.144438 0.647828 0.297756 0.029 Uiso 1 1 calc R . . . .
C00F C 0.7089(2) 0.52135(12) -0.0186(4) 0.0234(5) Uani 1 1 d . . . . .
H00F H 0.679129 0.494245 -0.148145 0.028 Uiso 1 1 calc R . . . .
C00G C 0.2779(2) 0.61106(13) 0.5141(4) 0.0244(5) Uani 1 1 d . . . . .
H00G H 0.230346 0.588868 0.620444 0.029 Uiso 1 1 calc R . . . .
C00H C 0.8295(2) 0.52192(13) 0.0409(4) 0.0250(5) Uani 1 1 d . . . . .
H00H H 0.880803 0.494794 -0.048166 0.030 Uiso 1 1 calc R . . . .
C00I C 1.0087(2) 0.68602(15) 0.7800(4) 0.0308(6) Uani 1 1 d . . . . .
H00I H 0.981761 0.738767 0.767718 0.046 Uiso 1 1 calc GR . . . .
H00J H 1.094024 0.684789 0.783375 0.046 Uiso 1 1 calc GR . . . .
H00K H 0.983181 0.663521 0.918686 0.046 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
O001 C002 1.371(3) . ?
O001 C00I 1.426(3) . ?
C002 C006 1.427(3) . ?
C002 C00D 1.371(3) . ?
C003 C004 1.434(3) . ?
C003 C006 1.426(3) . ?
C003 C007 1.421(3) . ?
C004 C005 1.495(3) . ?
C004 C009 1.369(3) . ?
C005 C008 1.403(3) . ?
C005 C00C 1.393(3) . ?
C006 C00B 1.421(3) . ?
C007 C00F 1.370(3) . ?
C008 C00A 1.385(3) . ?
C009 C00D 1.409(3) . ?
C00A C00E 1.386(3) . ?
C00B C00H 1.367(3) . ?
C00C C00G 1.388(3) . ?
C00E C00G 1.387(3) . ?
C00F C00H 1.406(3) . ?

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
C002 O001 C00I 116.46(18) . . ?
O001 C002 C006 114.49(19) . . ?
C00D C002 O001 124.8(2) . . ?
C00D C002 C006 120.8(2) . . ?
C006 C003 C004 119.51(19) . . ?
C007 C003 C004 122.50(19) . . ?
C007 C003 C006 117.96(19) . . ?
C003 C004 C005 121.94(19) . . ?
C009 C004 C003 118.55(19) . . ?
C009 C004 C005 119.50(19) . . ?
C008 C005 C004 121.73(19) . . ?
C00C C005 C004 119.77(19) . . ?
C00C C005 C008 118.5(2) . . ?
C003 C006 C002 118.95(19) . . ?
C00B C006 C002 121.9(2) . . ?
C00B C006 C003 119.2(2) . . ?
C00F C007 C003 121.6(2) . . ?
C00A C008 C005 120.3(2) . . ?
C004 C009 C00D 122.8(2) . . ?
C008 C00A C00E 120.6(2) . . ?
C00H C00B C006 120.8(2) . . ?
C00G C00C C005 121.0(2) . . ?
C002 C00D C009 119.3(2) . . ?
C00A C00E C00G 119.7(2) . . ?
C007 C00F C00H 120.0(2) . . ?
C00E C00G C00C 119.9(2) . . ?
C00B C00H C00F 120.5(2) . . ?

_olex2_date_sample_data_collection 2022-07-20
_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 1.330
_oxdiff_exptl_absorpt_empirical_full_min 0.771
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane'
_exptl_crystal_preparation       Luminescent
