# Supplementary Information (SI) for Organic & Biomolecular 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. 
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data_240826_htj_0_54_1
_audit_block_doi                 10.5517/ccdc.csd.cc2mzhhm
_database_code_depnum_ccdc_archive 'CCDC 2442381'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.5c01515 2025
loop_
_audit_author_name
_audit_author_address
'Cheng Ma'
;Zhejiang University
China
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_audit_creation_date             2024-08-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 Br Cl2 N O4 S'
_chemical_formula_sum            'C30 H24 Br Cl2 N O4 S'
_chemical_formula_weight         645.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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'
Br Br -0.9338 1.0006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3281 0.5435 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2925 0.4295 '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                   11.2175(5)
_cell_length_b                   15.8846(8)
_cell_length_c                   16.0861(8)
_cell_angle_alpha                90
_cell_angle_beta                 105.3450(10)
_cell_angle_gamma                90
_cell_volume                     2764.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9947
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.633
_cell_measurement_theta_min      3.465
_shelx_estimated_absorpt_T_max   0.831
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    3.194
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0599 before and 0.0514 after correction.
The Ratio of minimum to maximum transmission is 0.8811.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 0.963
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33139
_diffrn_reflns_point_group_measured_fraction_full 0.963
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.645
_diffrn_reflns_theta_min         3.757
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON III M28'
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'ZJU Bruker D8 VENTURE Metaljet PHOTON III'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'liquid Metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_type              'Bruker Excillum Metaljet D2+'
_diffrn_source_voltage           69.9
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5900
_reflns_number_total             6152
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.217
_refine_diff_density_min         -1.973
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     354
_refine_ls_number_reflns         6152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.037
_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)+(0.1092P)²+6.1008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.1733
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Rigid bond restraints
 Br1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
3.a Ternary CH refined with riding coordinates:
 C3(H3)
3.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C17(H17A,H17B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C19(H19), C20(H20),
 C22(H22), C23(H23), C26(H26), C27(H27), C28(H28), C29(H29), C30(H30)
3.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Br1 Br 0.84703(3) 0.53892(2) 0.93737(2) 0.03010(14) Uani 1 1 d . U . . .
Cl1 Cl 0.99267(6) 0.33261(5) 0.88722(5) 0.03011(19) Uani 1 1 d . . . . .
Cl2 Cl 0.82174(9) 0.25294(5) 0.63884(6) 0.0376(2) Uani 1 1 d . . . . .
S1 S 0.30014(6) 0.46387(4) 0.51518(4) 0.01522(16) Uani 1 1 d . . . . .
O1 O 0.4733(2) 0.57962(12) 0.64528(14) 0.0242(4) Uani 1 1 d . . . . .
O2 O 0.51777(18) 0.32327(12) 0.54724(12) 0.0181(4) Uani 1 1 d . . . . .
H2 H 0.566198 0.357134 0.532774 0.027 Uiso 1 1 calc R U . . .
O3 O 0.3260(2) 0.53754(13) 0.47188(14) 0.0237(4) Uani 1 1 d . . . . .
O4 O 0.26828(19) 0.38734(13) 0.46803(13) 0.0233(4) Uani 1 1 d . . . . .
N1 N 0.4267(2) 0.44297(14) 0.59402(14) 0.0146(4) Uani 1 1 d . . . . .
C1 C 0.6747(2) 0.50704(15) 0.78102(16) 0.0144(5) Uani 1 1 d . . . . .
H1 H 0.688108 0.564688 0.770606 0.017 Uiso 1 1 calc R U . . .
C2 C 0.7347(2) 0.47355(16) 0.85636(17) 0.0161(5) Uani 1 1 d . U . . .
C3 C 0.7132(2) 0.38556(15) 0.88456(16) 0.0141(5) Uani 1 1 d . . . . .
H3 H 0.775093 0.376489 0.941279 0.017 Uiso 1 1 calc R U . . .
C4 C 0.7435(2) 0.32183(15) 0.82261(16) 0.0139(5) Uani 1 1 d . . . . .
C5 C 0.6764(2) 0.31302(15) 0.73942(16) 0.0131(4) Uani 1 1 d . . . . .
C6 C 0.5868(2) 0.37600(15) 0.69625(15) 0.0124(4) Uani 1 1 d . . . . .
C7 C 0.5902(2) 0.45932(14) 0.71465(16) 0.0130(5) Uani 1 1 d . . . . .
C8 C 0.4930(2) 0.50440(16) 0.64988(17) 0.0152(5) Uani 1 1 d . . . . .
C9 C 0.4798(2) 0.35668(15) 0.61636(16) 0.0133(4) Uani 1 1 d . . . . .
C10 C 0.5858(2) 0.37320(17) 0.90071(16) 0.0162(5) Uani 1 1 d . . . . .
C11 C 0.5036(3) 0.4386(2) 0.8990(2) 0.0280(6) Uani 1 1 d . . . . .
H11 H 0.523449 0.493618 0.883649 0.034 Uiso 1 1 calc R U . . .
C12 C 0.3919(3) 0.4246(2) 0.9197(3) 0.0362(8) Uani 1 1 d . . . . .
H12 H 0.335508 0.469793 0.916864 0.043 Uiso 1 1 calc R U . . .
C13 C 0.3628(3) 0.3452(2) 0.9444(2) 0.0294(7) Uani 1 1 d . . . . .
H13 H 0.287281 0.335667 0.959029 0.035 Uiso 1 1 calc R U . . .
C14 C 0.4460(3) 0.2800(2) 0.9473(2) 0.0278(6) Uani 1 1 d . . . . .
H14 H 0.427625 0.225417 0.964758 0.033 Uiso 1 1 calc R U . . .
C15 C 0.5556(3) 0.29353(18) 0.9251(2) 0.0238(6) Uani 1 1 d . . . . .
H15 H 0.610842 0.247920 0.926506 0.029 Uiso 1 1 calc R U . . .
C16 C 0.8547(2) 0.26732(17) 0.86131(18) 0.0191(5) Uani 1 1 d . . . . .
H16A H 0.862405 0.222983 0.819782 0.023 Uiso 1 1 calc R U . . .
H16B H 0.844705 0.239626 0.914188 0.023 Uiso 1 1 calc R U . . .
C17 C 0.6967(3) 0.23746(16) 0.68815(18) 0.0185(5) Uani 1 1 d . . . . .
H17A H 0.619811 0.225610 0.642673 0.022 Uiso 1 1 calc R U . . .
H17B H 0.714942 0.187836 0.726673 0.022 Uiso 1 1 calc R U . . .
C18 C 0.1878(2) 0.48738(17) 0.56871(16) 0.0162(5) Uani 1 1 d . . . . .
C19 C 0.1049(3) 0.42470(19) 0.5766(2) 0.0243(6) Uani 1 1 d . . . . .
H19 H 0.105886 0.371363 0.550053 0.029 Uiso 1 1 calc R U . . .
C20 C 0.0207(3) 0.4416(2) 0.6240(2) 0.0331(7) Uani 1 1 d . . . . .
H20 H -0.036585 0.399345 0.629511 0.040 Uiso 1 1 calc R U . . .
C21 C 0.0186(3) 0.5186(3) 0.6633(2) 0.0340(7) Uani 1 1 d . . . . .
C22 C 0.1009(3) 0.5813(2) 0.6520(2) 0.0323(7) Uani 1 1 d . . . . .
H22 H 0.098295 0.635140 0.677199 0.039 Uiso 1 1 calc R U . . .
C23 C 0.1854(3) 0.5666(2) 0.6052(2) 0.0254(6) Uani 1 1 d . . . . .
H23 H 0.240774 0.609580 0.597965 0.030 Uiso 1 1 calc R U . . .
C24 C -0.0719(4) 0.5339(4) 0.7167(3) 0.0562(14) Uani 1 1 d . . . . .
H24A H -0.028645 0.529860 0.778094 0.084 Uiso 1 1 calc R U . . .
H24B H -0.137753 0.491597 0.702407 0.084 Uiso 1 1 calc R U . . .
H24C H -0.107955 0.590211 0.704287 0.084 Uiso 1 1 calc R U . . .
C25 C 0.3868(2) 0.29671(17) 0.63932(17) 0.0184(5) Uani 1 1 d . . . . .
C26 C 0.3636(3) 0.2179(2) 0.6009(2) 0.0301(7) Uani 1 1 d . . . . .
H26 H 0.406827 0.200125 0.560552 0.036 Uiso 1 1 calc R U . . .
C27 C 0.2762(4) 0.1646(3) 0.6218(2) 0.0463(11) Uani 1 1 d . . . . .
H27 H 0.261120 0.110451 0.596201 0.056 Uiso 1 1 calc R U . . .
C28 C 0.2119(4) 0.1908(3) 0.6797(2) 0.0458(11) Uani 1 1 d . . . . .
H28 H 0.150046 0.155640 0.691772 0.055 Uiso 1 1 calc R U . . .
C29 C 0.2379(3) 0.2683(3) 0.7200(2) 0.0371(8) Uani 1 1 d . . . . .
H29 H 0.195454 0.285540 0.760997 0.045 Uiso 1 1 calc R U . . .
C30 C 0.3262(3) 0.3208(2) 0.7006(2) 0.0256(6) Uani 1 1 d . . . . .
H30 H 0.345130 0.373365 0.729322 0.031 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
Br1 C2 1.870(3) . ?
Cl1 C16 1.817(3) . ?
Cl2 C17 1.802(3) . ?
S1 O3 1.430(2) . ?
S1 O4 1.427(2) . ?
S1 N1 1.667(2) . ?
S1 C18 1.744(3) . ?
O1 C8 1.214(3) . ?
O2 H2 0.8400 . ?
O2 C9 1.397(3) . ?
N1 C8 1.400(3) . ?
N1 C9 1.500(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.331(4) . ?
C1 C7 1.441(3) . ?
C2 C3 1.508(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.521(3) . ?
C3 C10 1.532(3) . ?
C4 C5 1.358(3) . ?
C4 C16 1.511(3) . ?
C5 C6 1.458(3) . ?
C5 C17 1.507(3) . ?
C6 C7 1.355(3) . ?
C6 C9 1.540(3) . ?
C7 C8 1.478(3) . ?
C9 C25 1.528(3) . ?
C10 C11 1.384(4) . ?
C10 C15 1.393(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.391(4) . ?
C18 C23 1.392(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.380(6) . ?
C21 C22 1.402(6) . ?
C21 C24 1.513(5) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(4) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.390(4) . ?
C25 C30 1.392(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.401(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.384(7) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.393(4) . ?
C30 H30 0.9500 . ?

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
O3 S1 N1 106.98(12) . . ?
O3 S1 C18 109.33(13) . . ?
O4 S1 O3 119.52(14) . . ?
O4 S1 N1 106.12(12) . . ?
O4 S1 C18 109.43(13) . . ?
N1 S1 C18 104.34(12) . . ?
C9 O2 H2 109.5 . . ?
C8 N1 S1 123.40(18) . . ?
C8 N1 C9 111.9(2) . . ?
C9 N1 S1 124.63(17) . . ?
C2 C1 H1 118.7 . . ?
C2 C1 C7 122.6(2) . . ?
C7 C1 H1 118.7 . . ?
C1 C2 Br1 119.8(2) . . ?
C1 C2 C3 124.2(2) . . ?
C3 C2 Br1 115.90(18) . . ?
C2 C3 H3 106.3 . . ?
C2 C3 C4 109.8(2) . . ?
C2 C3 C10 113.6(2) . . ?
C4 C3 H3 106.3 . . ?
C4 C3 C10 114.0(2) . . ?
C10 C3 H3 106.3 . . ?
C5 C4 C3 123.6(2) . . ?
C5 C4 C16 121.9(2) . . ?
C16 C4 C3 114.5(2) . . ?
C4 C5 C6 122.1(2) . . ?
C4 C5 C17 119.8(2) . . ?
C6 C5 C17 118.1(2) . . ?
C5 C6 C9 123.2(2) . . ?
C7 C6 C5 126.2(2) . . ?
C7 C6 C9 110.4(2) . . ?
C1 C7 C8 119.0(2) . . ?
C6 C7 C1 130.6(2) . . ?
C6 C7 C8 110.3(2) . . ?
O1 C8 N1 126.1(2) . . ?
O1 C8 C7 127.5(2) . . ?
N1 C8 C7 106.4(2) . . ?
O2 C9 N1 110.0(2) . . ?
O2 C9 C6 113.9(2) . . ?
O2 C9 C25 109.1(2) . . ?
N1 C9 C6 100.97(18) . . ?
N1 C9 C25 112.0(2) . . ?
C25 C9 C6 110.7(2) . . ?
C11 C10 C3 123.1(2) . . ?
C11 C10 C15 118.5(3) . . ?
C15 C10 C3 118.1(2) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.6 . . ?
C14 C13 C12 118.8(3) . . ?
C14 C13 H13 120.6 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
Cl1 C16 H16A 109.9 . . ?
Cl1 C16 H16B 109.9 . . ?
C4 C16 Cl1 109.12(18) . . ?
C4 C16 H16A 109.9 . . ?
C4 C16 H16B 109.9 . . ?
H16A C16 H16B 108.3 . . ?
Cl2 C17 H17A 109.1 . . ?
Cl2 C17 H17B 109.1 . . ?
C5 C17 Cl2 112.33(18) . . ?
C5 C17 H17A 109.1 . . ?
C5 C17 H17B 109.1 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 S1 118.6(2) . . ?
C19 C18 C23 121.4(3) . . ?
C23 C18 S1 119.9(2) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.7(3) . . ?
C20 C19 H19 120.7 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 C22 118.5(3) . . ?
C20 C21 C24 119.9(4) . . ?
C22 C21 C24 121.5(4) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.2 . . ?
C18 C23 H23 120.8 . . ?
C22 C23 C18 118.4(3) . . ?
C22 C23 H23 120.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C9 120.9(3) . . ?
C26 C25 C30 119.6(3) . . ?
C30 C25 C9 119.5(2) . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(4) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.9 . . ?
C28 C27 C26 120.2(4) . . ?
C28 C27 H27 119.9 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 119.9(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(4) . . ?
C30 C29 H29 120.0 . . ?
C25 C30 C29 120.2(3) . . ?
C25 C30 H30 119.9 . . ?
C29 C30 H30 119.9 . . ?


_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_rb139m
_database_code_depnum_ccdc_archive 'CCDC 2442327'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        
'9-methoxy-1-methylbenzo[h]quinolin-1-ium tetrafluoroborate'
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 B F4 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         311.08

_chemical_melting_point          479-481

_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                   6.7520(8)
_cell_length_b                   18.543(2)
_cell_length_c                   11.0244(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.642(4)
_cell_angle_gamma                90
_cell_volume                     1379.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6359
_cell_measurement_theta_min      2.1966
_cell_measurement_theta_max      25.6887
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            16157
_diffrn_reflns_av_R_equivalents  0.1291
_diffrn_reflns_av_unetI/netI     0.0856
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         26.04
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             2724
_reflns_number_gt                1670
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1212
_refine_ls_R_factor_gt           0.0677
_refine_ls_wR_factor_gt          0.1675
_refine_ls_wR_factor_ref         0.2075
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_number_reflns         2724
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+2.4240P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.551
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_computing_data_collection       'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX4 (Ver 2021.4-0, Bruker AXS Inc., 2021)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F F1 0.6019(3) 0.50542(13) 0.7313(2) 0.0455(7) Uani d . . . 1 . .
F F2 0.8780(3) 0.50114(13) 0.6189(2) 0.0458(7) Uani d . . . 1 . .
F F3 0.8919(4) 0.46223(13) 0.8138(2) 0.0483(7) Uani d . . . 1 . .
F F4 0.7223(3) 0.39688(12) 0.6710(2) 0.0449(7) Uani d . . . 1 . .
O O1 0.8771(4) 0.16139(14) 0.5312(2) 0.0356(7) Uani d . . . 1 . .
N N1 0.8196(4) 0.16912(16) 0.0453(3) 0.0312(7) Uani d . . . 1 . .
C C1 0.8488(5) 0.23686(19) 0.0987(3) 0.0281(8) Uani d . . . 1 . .
C C2 0.8317(5) 0.1598(2) -0.0744(3) 0.0317(9) Uani d . . . 1 . .
H H2 0.817612 0.112390 -0.105979 0.038000 Uiso calc U . R 1 . .
C C3 0.8635(5) 0.2154(2) -0.1544(4) 0.0336(9) Uani d . . . 1 . .
H H3 0.877051 0.206593 -0.238653 0.040000 Uiso calc U . R 1 . .
C C4 0.8748(5) 0.2844(2) -0.1077(3) 0.0322(9) Uani d . . . 1 . .
H H4 0.886944 0.324388 -0.160828 0.039000 Uiso calc U . R 1 . .
C C5 0.8686(5) 0.2956(2) 0.0174(3) 0.0308(9) Uani d . . . 1 . .
C C6 0.8529(5) 0.24884(19) 0.2289(3) 0.0276(8) Uani d . . . 1 . .
C C7 0.8488(5) 0.3219(2) 0.2688(3) 0.0293(8) Uani d . . . 1 . .
C C8 0.8585(5) 0.3802(2) 0.1841(4) 0.0335(9) Uani d . . . 1 . .
H H8 0.852889 0.428477 0.212544 0.040000 Uiso calc U . R 1 . .
C C9 0.8753(5) 0.3674(2) 0.0649(4) 0.0351(9) Uani d . . . 1 . .
H H9 0.892035 0.406780 0.011083 0.042000 Uiso calc U . R 1 . .
C C10 0.8695(5) 0.1943(2) 0.3187(3) 0.0291(8) Uani d . . . 1 . .
H H10 0.884032 0.145466 0.294526 0.035000 Uiso calc U . R 1 . .
C C11 0.8650(5) 0.2109(2) 0.4402(3) 0.0321(9) Uani d . . . 1 . .
C C12 0.8475(5) 0.2830(2) 0.4787(3) 0.0313(9) Uani d . . . 1 . .
H H12 0.838810 0.294058 0.562532 0.038000 Uiso calc U . R 1 . .
C C13 0.8433(5) 0.3369(2) 0.3938(4) 0.0333(9) Uani d . . . 1 . .
H H13 0.836360 0.385625 0.419928 0.040000 Uiso calc U . R 1 . .
C C14 0.7420(6) 0.1047(2) 0.1122(4) 0.0415(10) Uani d . . . 1 . .
H H14A 0.667921 0.073520 0.055235 0.062000 Uiso calc U . R 1 . .
H H14B 0.654283 0.120956 0.175976 0.062000 Uiso calc U . R 1 . .
H H14C 0.853262 0.077717 0.148752 0.062000 Uiso calc U . R 1 . .
C C15 0.8830(6) 0.0867(2) 0.4966(4) 0.0403(10) Uani d . . . 1 . .
H H15A 0.885237 0.056495 0.569539 0.060000 Uiso calc U . R 1 . .
H H15B 1.002405 0.077629 0.450503 0.060000 Uiso calc U . R 1 . .
H H15C 0.765387 0.075183 0.446190 0.060000 Uiso calc U . R 1 . .
B B1 0.7739(7) 0.4671(2) 0.7087(4) 0.0343(10) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 B1 . 1.391(5) ?
F2 B1 . 1.383(5) ?
F3 B1 . 1.390(5) ?
F4 B1 . 1.407(5) ?
O1 C11 . 1.361(5) ?
O1 C15 . 1.437(5) ?
N1 C2 . 1.336(5) ?
N1 C1 . 1.399(5) ?
N1 C14 . 1.505(5) ?
C1 C5 . 1.420(5) ?
C1 C6 . 1.452(5) ?
C2 C3 . 1.378(5) ?
C3 C4 . 1.380(6) ?
C4 C5 . 1.397(5) ?
C5 C9 . 1.430(6) ?
C6 C10 . 1.417(5) ?
C6 C7 . 1.424(5) ?
C7 C13 . 1.407(5) ?
C7 C8 . 1.431(5) ?
C8 C9 . 1.344(5) ?
C10 C11 . 1.376(5) ?
C11 C12 . 1.408(5) ?
C12 C13 . 1.369(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C15 . . 117.1(3) ?
C2 N1 C1 . . 121.3(3) ?
C2 N1 C14 . . 114.4(3) ?
C1 N1 C14 . . 123.6(3) ?
N1 C1 C5 . . 116.0(3) ?
N1 C1 C6 . . 123.5(3) ?
C5 C1 C6 . . 120.5(3) ?
N1 C2 C3 . . 123.5(4) ?
C2 C3 C4 . . 117.5(4) ?
C3 C4 C5 . . 120.2(4) ?
C4 C5 C1 . . 121.0(4) ?
C4 C5 C9 . . 119.9(4) ?
C1 C5 C9 . . 119.1(3) ?
C10 C6 C7 . . 117.7(3) ?
C10 C6 C1 . . 125.5(3) ?
C7 C6 C1 . . 116.8(3) ?
C13 C7 C6 . . 119.4(3) ?
C13 C7 C8 . . 119.5(3) ?
C6 C7 C8 . . 121.0(3) ?
C9 C8 C7 . . 120.8(4) ?
C8 C9 C5 . . 121.3(4) ?
C11 C10 C6 . . 121.1(3) ?
O1 C11 C10 . . 124.4(4) ?
O1 C11 C12 . . 114.9(3) ?
C10 C11 C12 . . 120.7(4) ?
C13 C12 C11 . . 119.1(4) ?
C12 C13 C7 . . 121.6(4) ?
F2 B1 F3 . . 109.6(3) ?
F2 B1 F1 . . 109.8(3) ?
F3 B1 F1 . . 110.2(3) ?
F2 B1 F4 . . 109.8(3) ?
F3 B1 F4 . . 108.5(3) ?
F1 B1 F4 . . 108.9(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# 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_rb136s
_database_code_depnum_ccdc_archive 'CCDC 2442320'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        7-methoxybenzo[h]quinoline
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         209.24

_chemical_melting_point          394-396

_space_group_crystal_system      monoclinic
_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                   6.8333(4)
_cell_length_b                   10.9215(7)
_cell_length_c                   27.6222(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.331(3)
_cell_angle_gamma                90
_cell_volume                     2048.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5842
_cell_measurement_theta_min      5.1753
_cell_measurement_theta_max      67.6197
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880

_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            20992
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.0727
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         68.02
_diffrn_reflns_theta_full        68.02
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32

_refine_special_details          
;
;

_reflns_number_total             3662
_reflns_number_gt                2697
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_gt          0.2324
_refine_ls_wR_factor_ref         0.2521
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      0.955
_refine_ls_number_reflns         3662
_refine_ls_number_parameters     413
_refine_ls_number_restraints     1015
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1317P)²+1.7697P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.399
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1A -0.2583(6) 0.0309(3) 0.46089(14) 0.0293(9) Uani d U P D 0.804(3) A 1
H H1A -0.294803 0.028457 0.493082 0.035 Uiso calc U P R 0.804(3) A 1
C C2A -0.3793(5) -0.0287(3) 0.42444(13) 0.0298(7) Uani d U P D 0.804(3) A 1
H H2A -0.494006 -0.071014 0.431713 0.036 Uiso calc U P R 0.804(3) A 1
C C3A -0.3287(5) -0.0248(3) 0.37755(12) 0.0286(7) Uani d U P D 0.804(3) A 1
H H3A -0.41025 -0.063225 0.351874 0.034 Uiso calc U P R 0.804(3) A 1
C C13A -0.0408(4) 0.0938(3) 0.40704(11) 0.0218(7) Uani d U P D 0.804(3) A 1
C C4A -0.1559(4) 0.0362(3) 0.36773(11) 0.0240(7) Uani d U P D 0.804(3) A 1
C C5A -0.0918(5) 0.0401(3) 0.32020(11) 0.0255(8) Uani d U P D 0.804(3) A 1
H H5A -0.168884 0.002389 0.293588 0.031 Uiso calc U P R 0.804(3) A 1
C C6A 0.0796(5) 0.0978(3) 0.31289(11) 0.0248(7) Uani d U P D 0.804(3) A 1
H H6A 0.122206 0.097466 0.281296 0.03 Uiso calc U P R 0.804(3) A 1
C C7A 0.1950(5) 0.1581(3) 0.35131(10) 0.0218(7) Uani d U P D 0.804(3) A 1
C C12A 0.1366(4) 0.1570(3) 0.39910(11) 0.0215(7) Uani d U P D 0.804(3) A 1
C C11A 0.2510(5) 0.2194(3) 0.43682(11) 0.0240(7) Uani d U P D 0.804(3) A 1
H H11A 0.213979 0.21748 0.468964 0.029 Uiso calc U P R 0.804(3) A 1
C C10A 0.4167(5) 0.2832(3) 0.42728(11) 0.0270(7) Uani d U P D 0.804(3) A 1
H H10A 0.492041 0.325934 0.452878 0.032 Uiso calc U P R 0.804(3) A 1
C C9A 0.4750(5) 0.2857(3) 0.38018(11) 0.0267(7) Uani d U P D 0.804(3) A 1
H H9A 0.589023 0.330198 0.373907 0.032 Uiso calc U P R 0.804(3) A 1
C C8A 0.3664(4) 0.2233(3) 0.34298(11) 0.0238(7) Uani d U P D 0.804(3) A 1
C C14A 0.5746(5) 0.2921(3) 0.28379(13) 0.0311(8) Uani d U P D 0.804(3) A 1
H H14A 0.587797 0.284257 0.248953 0.047 Uiso calc U P R 0.804(3) A 1
H H14B 0.695632 0.263441 0.302746 0.047 Uiso calc U P R 0.804(3) A 1
H H14C 0.552059 0.378171 0.291573 0.047 Uiso calc U P R 0.804(3) A 1
N N1A -0.0941(5) 0.0913(3) 0.45356(10) 0.0255(7) Uani d U P D 0.804(3) A 1
O O1A 0.4121(4) 0.2200(2) 0.29558(8) 0.0280(6) Uani d U P D 0.804(3) A 1
C C1B 0.4989(18) 0.2353(13) 0.2844(4) 0.026(2) Uani d U P D 0.196(3) A 2
H H1B 0.536888 0.23557 0.252311 0.031 Uiso calc U P R 0.196(3) A 2
C C2B 0.6180(16) 0.2972(11) 0.3206(4) 0.030(2) Uani d U P D 0.196(3) A 2
H H2B 0.734356 0.337704 0.313419 0.036 Uiso calc U P R 0.196(3) A 2
C C3B 0.5625(16) 0.2981(11) 0.3670(4) 0.027(2) Uani d U P D 0.196(3) A 2
H H3B 0.638911 0.341379 0.392286 0.032 Uiso calc U P R 0.196(3) A 2
C C13B 0.2798(10) 0.1744(7) 0.3390(2) 0.0196(18) Uani d U P DG 0.196(3) A 2
C C4B 0.3916(10) 0.2344(7) 0.3769(3) 0.0240(17) Uani d U P DG 0.196(3) A 2
C C5B 0.3315(11) 0.2340(7) 0.4234(2) 0.025(2) Uani d U P DG 0.196(3) A 2
H H5B 0.407952 0.274929 0.449308 0.03 Uiso calc U P R 0.196(3) A 2
C C6B 0.1596(11) 0.1736(7) 0.43197(19) 0.0231(19) Uani d U P DG 0.196(3) A 2
H H6B 0.118542 0.173289 0.463727 0.028 Uiso calc U P R 0.196(3) A 2
C C7B 0.0478(9) 0.1136(6) 0.39407(18) 0.0220(18) Uani d U P DG 0.196(3) A 2
C C12B 0.1079(9) 0.1140(6) 0.34761(18) 0.0211(17) Uani d U P DG 0.196(3) A 2
C C11B -0.0039(11) 0.0541(7) 0.3097(2) 0.024(2) Uani d U P DG 0.196(3) A 2
H H11B 0.037139 0.054384 0.277952 0.029 Uiso calc U P R 0.196(3) A 2
C C10B -0.1758(11) -0.0063(7) 0.3183(3) 0.026(2) Uani d U P DG 0.196(3) A 2
H H10B -0.252272 -0.047257 0.292369 0.032 Uiso calc U P R 0.196(3) A 2
C C9B -0.2359(10) -0.0067(7) 0.3647(3) 0.027(2) Uani d U P DG 0.196(3) A 2
H H9B -0.353443 -0.047971 0.370588 0.032 Uiso calc U P R 0.196(3) A 2
C C8B -0.1241(10) 0.0532(7) 0.4026(2) 0.0253(18) Uani d U P DG 0.196(3) A 2
C C14B -0.349(2) -0.0164(14) 0.4587(6) 0.037(3) Uani d U P D 0.196(3) A 2
H H14D -0.35773 -0.018517 0.493837 0.055 Uiso calc U P R 0.196(3) A 2
H H14E -0.335777 -0.100124 0.44662 0.055 Uiso calc U P R 0.196(3) A 2
H H14F -0.467528 0.021336 0.442062 0.055 Uiso calc U P R 0.196(3) A 2
N N1B 0.3340(15) 0.1752(10) 0.2921(3) 0.0222(19) Uani d U P D 0.196(3) A 2
O O1B -0.1799(18) 0.0536(10) 0.4493(3) 0.026(2) Uani d U P D 0.196(3) A 2
C C15 0.7636(4) 0.2812(2) 0.53706(10) 0.0326(6) Uani d . . . 1.0 . .
H H15 0.802834 0.281665 0.505119 0.039 Uiso calc U . R 1.0 . .
C C16 0.8837(4) 0.2196(2) 0.57336(10) 0.0344(7) Uani d . . . 1.0 . .
H H16 0.999851 0.178848 0.566156 0.041 Uiso calc U . R 1.0 . .
C C17 0.8292(4) 0.2195(2) 0.61992(10) 0.0325(6) Uani d . . . 1.0 . .
H H17 0.908502 0.179336 0.645527 0.039 Uiso calc U . R 1.0 . .
C C18 0.6555(4) 0.2793(2) 0.62917(10) 0.0277(6) Uani d . . . 1.0 . .
C C19 0.5879(4) 0.2814(2) 0.67665(10) 0.0310(6) Uani d . . . 1.0 . .
H H19 0.663823 0.242366 0.703149 0.037 Uiso calc U . R 1.0 . .
C C20 0.4178(4) 0.3380(2) 0.68415(9) 0.0292(6) Uani d . . . 1.0 . .
H H20 0.375113 0.337066 0.715743 0.035 Uiso calc U . R 1.0 . .
C C21 0.3008(3) 0.3993(2) 0.64524(9) 0.0253(6) Uani d . . . 1.0 . .
C C22 0.1275(4) 0.4640(2) 0.65321(9) 0.0290(6) Uani d . . . 1.0 . .
C C23 0.0188(4) 0.5250(2) 0.61617(10) 0.0330(6) Uani d . . . 1.0 . .
H H23 -0.096875 0.568235 0.622083 0.04 Uiso calc U . R 1.0 . .
C C24 0.0806(4) 0.5228(2) 0.56920(10) 0.0314(6) Uani d . . . 1.0 . .
H H24 0.004702 0.564726 0.54347 0.038 Uiso calc U . R 1.0 . .
C C25 0.2472(4) 0.4619(2) 0.55962(9) 0.0287(6) Uani d . . . 1.0 . .
H H25 0.285221 0.461199 0.527552 0.034 Uiso calc U . R 1.0 . .
C C26 0.3623(3) 0.4000(2) 0.59760(9) 0.0253(6) Uani d . . . 1.0 . .
C C27 0.5422(4) 0.3377(2) 0.59002(9) 0.0258(6) Uani d . . . 1.0 . .
C C28 -0.0795(4) 0.5329(3) 0.71249(11) 0.0393(7) Uani d . . . 1.0 . .
H H28A -0.098844 0.520623 0.746787 0.059 Uiso calc U . R 1.0 . .
H H28B -0.199449 0.50931 0.691843 0.059 Uiso calc U . R 1.0 . .
H H28C -0.050328 0.619267 0.706963 0.059 Uiso calc U . R 1.0 . .
N N2 0.5992(3) 0.33883(19) 0.54407(8) 0.0292(5) Uani d . . . 1.0 . .
O O2 0.0813(3) 0.45895(17) 0.70065(7) 0.0348(5) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1A N1A . 1.336(5) ?
C1A C2A . 1.392(5) ?
C1A H1A . 0.95 ?
C2A C3A . 1.378(5) ?
C2A H2A . 0.95 ?
C3A C4A . 1.408(4) ?
C3A H3A . 0.95 ?
C13A N1A . 1.374(4) ?
C13A C4A . 1.416(4) ?
C13A C12A . 1.433(4) ?
C4A C5A . 1.430(4) ?
C5A C6A . 1.364(4) ?
C5A H5A . 0.95 ?
C6A C7A . 1.413(4) ?
C6A H6A . 0.95 ?
C7A C8A . 1.412(4) ?
C7A C12A . 1.421(4) ?
C12A C11A . 1.407(4) ?
C11A C10A . 1.380(4) ?
C11A H11A . 0.95 ?
C10A C9A . 1.402(4) ?
C10A H10A . 0.95 ?
C9A C8A . 1.379(4) ?
C9A H9A . 0.95 ?
C8A O1A . 1.380(4) ?
C14A O1A . 1.428(4) ?
C14A H14A . 0.98 ?
C14A H14B . 0.98 ?
C14A H14C . 0.98 ?
C1B N1B . 1.341(10) ?
C1B C2B . 1.392(10) ?
C1B H1B . 0.95 ?
C2B C3B . 1.378(10) ?
C2B H2B . 0.95 ?
C3B C4B . 1.412(8) ?
C3B H3B . 0.95 ?
C13B N1B . 1.388(7) ?
C13B C4B . 1.39 ?
C13B C12B . 1.39 ?
C4B C5B . 1.39 ?
C5B C6B . 1.39 ?
C5B H5B . 0.95 ?
C6B C7B . 1.39 ?
C6B H6B . 0.95 ?
C7B C12B . 1.39 ?
C7B C8B . 1.39 ?
C12B C11B . 1.39 ?
C11B C10B . 1.39 ?
C11B H11B . 0.95 ?
C10B C9B . 1.39 ?
C10B H10B . 0.95 ?
C9B C8B . 1.39 ?
C9B H9B . 0.95 ?
C8B O1B . 1.384(8) ?
C14B O1B . 1.430(10) ?
C14B H14D . 0.98 ?
C14B H14E . 0.98 ?
C14B H14F . 0.98 ?
C15 N2 . 1.320(3) ?
C15 C16 . 1.397(4) ?
C15 H15 . 0.95 ?
C16 C17 . 1.378(4) ?
C16 H16 . 0.95 ?
C17 C18 . 1.402(3) ?
C17 H17 . 0.95 ?
C18 C27 . 1.412(4) ?
C18 C19 . 1.438(3) ?
C19 C20 . 1.353(4) ?
C19 H19 . 0.95 ?
C20 C21 . 1.433(4) ?
C20 H20 . 0.95 ?
C21 C22 . 1.417(3) ?
C21 C26 . 1.425(3) ?
C22 C23 . 1.370(4) ?
C22 O2 . 1.382(3) ?
C23 C24 . 1.408(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.370(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.412(4) ?
C25 H25 . 0.95 ?
C26 C27 . 1.440(3) ?
C27 N2 . 1.368(3) ?
C28 O2 . 1.430(3) ?
C28 H28A . 0.98 ?
C28 H28B . 0.98 ?
C28 H28C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1A C1A C2A . . 124.3(4) ?
N1A C1A H1A . . 117.9 ?
C2A C1A H1A . . 117.9 ?
C3A C2A C1A . . 118.3(3) ?
C3A C2A H2A . . 120.8 ?
C1A C2A H2A . . 120.8 ?
C2A C3A C4A . . 119.9(3) ?
C2A C3A H3A . . 120.0 ?
C4A C3A H3A . . 120.0 ?
N1A C13A C4A . . 121.7(3) ?
N1A C13A C12A . . 118.0(3) ?
C4A C13A C12A . . 120.3(3) ?
C3A C4A C13A . . 118.0(3) ?
C3A C4A C5A . . 122.7(3) ?
C13A C4A C5A . . 119.3(3) ?
C6A C5A C4A . . 120.3(3) ?
C6A C5A H5A . . 119.8 ?
C4A C5A H5A . . 119.8 ?
C5A C6A C7A . . 121.4(3) ?
C5A C6A H6A . . 119.3 ?
C7A C6A H6A . . 119.3 ?
C8A C7A C6A . . 121.1(3) ?
C8A C7A C12A . . 118.6(3) ?
C6A C7A C12A . . 120.2(3) ?
C11A C12A C7A . . 119.6(3) ?
C11A C12A C13A . . 122.0(3) ?
C7A C12A C13A . . 118.4(3) ?
C10A C11A C12A . . 120.3(3) ?
C10A C11A H11A . . 119.9 ?
C12A C11A H11A . . 119.9 ?
C11A C10A C9A . . 120.7(3) ?
C11A C10A H10A . . 119.7 ?
C9A C10A H10A . . 119.7 ?
C8A C9A C10A . . 119.8(3) ?
C8A C9A H9A . . 120.1 ?
C10A C9A H9A . . 120.1 ?
C9A C8A O1A . . 124.1(3) ?
C9A C8A C7A . . 121.1(3) ?
O1A C8A C7A . . 114.9(3) ?
O1A C14A H14A . . 109.5 ?
O1A C14A H14B . . 109.5 ?
H14A C14A H14B . . 109.5 ?
O1A C14A H14C . . 109.5 ?
H14A C14A H14C . . 109.5 ?
H14B C14A H14C . . 109.5 ?
C1A N1A C13A . . 117.7(3) ?
C8A O1A C14A . . 117.7(3) ?
N1B C1B C2B . . 123.9(10) ?
N1B C1B H1B . . 118.0 ?
C2B C1B H1B . . 118.0 ?
C3B C2B C1B . . 118.3(9) ?
C3B C2B H2B . . 120.9 ?
C1B C2B H2B . . 120.9 ?
C2B C3B C4B . . 119.7(8) ?
C2B C3B H3B . . 120.2 ?
C4B C3B H3B . . 120.2 ?
N1B C13B C4B . . 121.3(5) ?
N1B C13B C12B . . 118.7(5) ?
C4B C13B C12B . . 120.0 ?
C5B C4B C13B . . 120.0 ?
C5B C4B C3B . . 121.0(5) ?
C13B C4B C3B . . 118.9(5) ?
C4B C5B C6B . . 120.0 ?
C4B C5B H5B . . 120.0 ?
C6B C5B H5B . . 120.0 ?
C7B C6B C5B . . 120.0 ?
C7B C6B H6B . . 120.0 ?
C5B C6B H6B . . 120.0 ?
C6B C7B C12B . . 120.0 ?
C6B C7B C8B . . 120.0 ?
C12B C7B C8B . . 120.0 ?
C11B C12B C7B . . 120.0 ?
C11B C12B C13B . . 120.0 ?
C7B C12B C13B . . 120.0 ?
C12B C11B C10B . . 120.0 ?
C12B C11B H11B . . 120.0 ?
C10B C11B H11B . . 120.0 ?
C9B C10B C11B . . 120.0 ?
C9B C10B H10B . . 120.0 ?
C11B C10B H10B . . 120.0 ?
C10B C9B C8B . . 120.0 ?
C10B C9B H9B . . 120.0 ?
C8B C9B H9B . . 120.0 ?
C9B C8B C7B . . 120.0 ?
O1B C14B H14D . . 109.5 ?
O1B C14B H14E . . 109.5 ?
H14D C14B H14E . . 109.5 ?
O1B C14B H14F . . 109.5 ?
H14D C14B H14F . . 109.5 ?
H14E C14B H14F . . 109.5 ?
C1B N1B C13B . . 117.8(8) ?
C8B O1B C14B . . 118.6(10) ?
N2 C15 C16 . . 124.5(2) ?
N2 C15 H15 . . 117.7 ?
C16 C15 H15 . . 117.7 ?
C17 C16 C15 . . 118.2(2) ?
C17 C16 H16 . . 120.9 ?
C15 C16 H16 . . 120.9 ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C17 C18 C27 . . 118.3(2) ?
C17 C18 C19 . . 122.5(2) ?
C27 C18 C19 . . 119.2(2) ?
C20 C19 C18 . . 121.0(2) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C21 . . 121.1(2) ?
C19 C20 H20 . . 119.5 ?
C21 C20 H20 . . 119.5 ?
C22 C21 C26 . . 118.5(2) ?
C22 C21 C20 . . 121.5(2) ?
C26 C21 C20 . . 119.9(2) ?
C23 C22 O2 . . 124.5(2) ?
C23 C22 C21 . . 121.4(2) ?
O2 C22 C21 . . 114.2(2) ?
C22 C23 C24 . . 119.1(2) ?
C22 C23 H23 . . 120.4 ?
C24 C23 H23 . . 120.4 ?
C25 C24 C23 . . 121.8(2) ?
C25 C24 H24 . . 119.1 ?
C23 C24 H24 . . 119.1 ?
C24 C25 C26 . . 119.7(2) ?
C24 C25 H25 . . 120.1 ?
C26 C25 H25 . . 120.1 ?
C25 C26 C21 . . 119.5(2) ?
C25 C26 C27 . . 122.2(2) ?
C21 C26 C27 . . 118.4(2) ?
N2 C27 C18 . . 121.8(2) ?
N2 C27 C26 . . 117.8(2) ?
C18 C27 C26 . . 120.5(2) ?
O2 C28 H28A . . 109.5 ?
O2 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
O2 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?
C15 N2 C27 . . 117.8(2) ?
C22 O2 C28 . . 117.1(2) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_rb137s
_database_code_depnum_ccdc_archive 'CCDC 2442321'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        8-methoxybenzo[h]quinoline
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         209.24

_chemical_melting_point          438-440

_space_group_crystal_system      monoclinic
_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                   7.9787(5)
_cell_length_b                   11.7412(6)
_cell_length_c                   11.6996(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.187(3)
_cell_angle_gamma                90
_cell_volume                     1041.26(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3907
_cell_measurement_theta_min      5.4805
_cell_measurement_theta_max      66.5877
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440

_exptl_absorpt_coefficient_mu    0.669
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5103
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_theta_min         5.48
_diffrn_reflns_theta_max         66.60
_diffrn_reflns_theta_full        66.60
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
;

_reflns_number_total             1795
_reflns_number_gt                1641
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0388
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1150
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_number_reflns         1795
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0606P)²+0.2533P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.210
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.09852(17) 0.40875(12) 0.82097(12) 0.0310(3) Uani d . . . 1 . .
H H1A 0.035593 0.480996 0.797701 0.047 Uiso calc U . R 1 . .
H H1B 0.06213 0.373164 0.885228 0.047 Uiso calc U . R 1 . .
H H1C 0.070494 0.357777 0.751205 0.047 Uiso calc U . R 1 . .
C C2 0.35641(16) 0.48553(10) 0.78707(11) 0.0218(3) Uani d . . . 1 . .
C C3 0.26388(16) 0.52473(10) 0.67374(11) 0.0220(3) Uani d . . . 1 . .
H H3 0.139976 0.513528 0.642592 0.026 Uiso calc U . R 1 . .
C C4 0.35465(16) 0.58170(9) 0.60418(10) 0.0206(3) Uani d . . . 1 . .
C C5 0.26091(16) 0.62251(10) 0.48539(11) 0.0230(3) Uani d . . . 1 . .
H H5 0.137255 0.610485 0.45365 0.028 Uiso calc U . R 1 . .
C C6 0.34582(16) 0.67769(10) 0.41812(11) 0.0232(3) Uani d . . . 1 . .
H H6 0.280608 0.70397 0.340105 0.028 Uiso calc U . R 1 . .
C C7 0.53203(16) 0.69720(10) 0.46234(11) 0.0212(3) Uani d . . . 1 . .
C C8 0.62397(17) 0.75464(10) 0.39503(11) 0.0241(3) Uani d . . . 1 . .
H H8 0.56279 0.78337 0.317268 0.029 Uiso calc U . R 1 . .
C C9 0.80338(17) 0.76885(10) 0.44283(11) 0.0255(3) Uani d . . . 1 . .
H H9 0.868537 0.806778 0.398713 0.031 Uiso calc U . R 1 . .
C C10 0.88758(16) 0.72601(11) 0.55812(11) 0.0244(3) Uani d . . . 1 . .
H H10 1.011436 0.736701 0.590732 0.029 Uiso calc U . R 1 . .
C C11 0.62914(16) 0.65703(10) 0.57807(10) 0.0204(3) Uani d . . . 1 . .
C C12 0.53796(16) 0.59911(10) 0.65054(10) 0.0202(3) Uani d . . . 1 . .
C C13 0.62800(16) 0.55848(10) 0.76760(10) 0.0218(3) Uani d . . . 1 . .
H H13 0.751721 0.569681 0.800373 0.026 Uiso calc U . R 1 . .
C C14 0.53928(17) 0.50337(10) 0.83406(11) 0.0226(3) Uani d . . . 1 . .
H H14 0.601695 0.476941 0.912571 0.027 Uiso calc U . R 1 . .
N N1 0.80632(13) 0.67155(9) 0.62493(9) 0.0228(3) Uani d . . . 1 . .
O O1 0.28399(11) 0.42960(8) 0.86286(7) 0.0267(3) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 O1 . 1.4273(15) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 O1 . 1.3679(14) ?
C2 C3 . 1.3798(18) ?
C2 C14 . 1.4051(18) ?
C3 C4 . 1.4150(17) ?
C3 H3 . 0.95 ?
C4 C12 . 1.4071(17) ?
C4 C5 . 1.4393(17) ?
C5 C6 . 1.3531(18) ?
C5 H5 . 0.95 ?
C6 C7 . 1.4310(18) ?
C6 H6 . 0.95 ?
C7 C8 . 1.4049(18) ?
C7 C11 . 1.4147(18) ?
C8 C9 . 1.3747(18) ?
C8 H8 . 0.95 ?
C9 C10 . 1.3993(19) ?
C9 H9 . 0.95 ?
C10 N1 . 1.3254(16) ?
C10 H10 . 0.95 ?
C11 N1 . 1.3581(16) ?
C11 C12 . 1.4476(17) ?
C12 C13 . 1.4160(17) ?
C13 C14 . 1.3667(18) ?
C13 H13 . 0.95 ?
C14 H14 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 H1A . . 109.5 ?
O1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
O1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
O1 C2 C3 . . 125.13(11) ?
O1 C2 C14 . . 114.52(11) ?
C3 C2 C14 . . 120.33(12) ?
C2 C3 C4 . . 119.60(11) ?
C2 C3 H3 . . 120.2 ?
C4 C3 H3 . . 120.2 ?
C12 C4 C3 . . 120.27(11) ?
C12 C4 C5 . . 119.22(11) ?
C3 C4 C5 . . 120.51(11) ?
C6 C5 C4 . . 121.16(11) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 121.21(11) ?
C5 C6 H6 . . 119.4 ?
C7 C6 H6 . . 119.4 ?
C8 C7 C11 . . 118.08(12) ?
C8 C7 C6 . . 122.62(11) ?
C11 C7 C6 . . 119.29(11) ?
C9 C8 C7 . . 119.33(11) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C10 . . 118.31(11) ?
C8 C9 H9 . . 120.8 ?
C10 C9 H9 . . 120.8 ?
N1 C10 C9 . . 124.46(12) ?
N1 C10 H10 . . 117.8 ?
C9 C10 H10 . . 117.8 ?
N1 C11 C7 . . 122.32(11) ?
N1 C11 C12 . . 118.20(11) ?
C7 C11 C12 . . 119.47(11) ?
C4 C12 C13 . . 118.45(11) ?
C4 C12 C11 . . 119.63(11) ?
C13 C12 C11 . . 121.92(11) ?
C14 C13 C12 . . 120.88(11) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C13 C14 C2 . . 120.46(11) ?
C13 C14 H14 . . 119.8 ?
C2 C14 H14 . . 119.8 ?
C10 N1 C11 . . 117.49(11) ?
C2 O1 C1 . . 117.52(10) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_rb134s
_database_code_depnum_ccdc_archive 'CCDC 2442325'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        5,7-dimethoxyphenanthrene-3-carbonitrile
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         263.28

_chemical_melting_point          399-401

_space_group_crystal_system      monoclinic
_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                   4.3852(11)
_cell_length_b                   14.944(4)
_cell_length_c                   19.737(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.417(19)
_cell_angle_gamma                90
_cell_volume                     1289.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1581
_cell_measurement_theta_min      3.7140
_cell_measurement_theta_max      66.1577
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.46
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            7484
_diffrn_reflns_av_R_equivalents  0.1145
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_theta_min         4.49
_diffrn_reflns_theta_max         66.80
_diffrn_reflns_theta_full        66.80
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23

_refine_special_details          
;
;

_reflns_number_total             2269
_reflns_number_gt                1338
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1297
_refine_ls_R_factor_gt           0.0863
_refine_ls_wR_factor_gt          0.2225
_refine_ls_wR_factor_ref         0.2722
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         2269
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1341P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.502
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.1039(9) 0.2883(3) 0.4886(2) 0.0354(10) Uani d . . . 1 . .
C C2 0.0471(9) 0.2444(3) 0.5457(2) 0.0333(10) Uani d . . . 1 . .
C C3 -0.0333(9) 0.1562(3) 0.5628(2) 0.0354(10) Uani d . . . 1 . .
H H3 -0.179749 0.123553 0.534747 0.043 Uiso calc U . R 1 . .
C C4 0.1032(10) 0.1190(3) 0.6202(2) 0.0359(10) Uani d . . . 1 . .
H H4 0.046716 0.060088 0.632388 0.043 Uiso calc U . R 1 . .
C C5 0.3276(9) 0.1652(2) 0.6626(2) 0.0319(9) Uani d . . . 1 . .
C C6 0.4519(9) 0.1247(3) 0.7233(2) 0.0353(10) Uani d . . . 1 . .
H H6 0.390689 0.065884 0.734414 0.042 Uiso calc U . R 1 . .
C C7 0.6584(9) 0.1691(2) 0.7659(2) 0.0336(10) Uani d . . . 1 . .
H H7 0.737121 0.140912 0.806651 0.04 Uiso calc U . R 1 . .
C C8 0.7601(9) 0.2577(3) 0.7506(2) 0.0314(9) Uani d . . . 1 . .
C C9 0.9772(9) 0.2980(3) 0.7976(2) 0.0337(10) Uani d . . . 1 . .
H H9 1.047509 0.267731 0.838148 0.04 Uiso calc U . R 1 . .
C C10 1.0846(9) 0.3816(3) 0.7838(2) 0.0320(9) Uani d . . . 1 . .
C C11 0.9823(9) 0.4262(2) 0.7228(2) 0.0331(10) Uani d . . . 1 . .
H H11 1.061138 0.483756 0.713506 0.04 Uiso calc U . R 1 . .
C C12 0.7710(8) 0.3873(2) 0.6772(2) 0.0296(9) Uani d . . . 1 . .
C C13 0.6442(9) 0.3006(2) 0.6898(2) 0.0303(9) Uani d . . . 1 . .
C C14 0.4140(8) 0.2541(2) 0.6448(2) 0.0301(9) Uani d . . . 1 . .
C C15 0.2714(9) 0.2915(3) 0.5856(2) 0.0328(9) Uani d . . . 1 . .
H H15 0.327757 0.34984 0.572118 0.039 Uiso calc U . R 1 . .
C C16 0.8179(10) 0.5103(3) 0.6005(2) 0.0392(11) Uani d . . . 1 . .
H H16A 0.781123 0.5562 0.634443 0.059 Uiso calc U . R 1 . .
H H16B 0.733795 0.530404 0.555639 0.059 Uiso calc U . R 1 . .
H H16C 1.038396 0.500349 0.599627 0.059 Uiso calc U . R 1 . .
C C17 1.3821(11) 0.3902(3) 0.8892(2) 0.0408(10) Uani d . . . 1 . .
H H17A 1.202603 0.378546 0.914492 0.061 Uiso calc U . R 1 . .
H H17B 1.520472 0.431271 0.915197 0.061 Uiso calc U . R 1 . .
H H17C 1.488669 0.333795 0.88183 0.061 Uiso calc U . R 1 . .
N N1 -0.2320(9) 0.3234(3) 0.4426(2) 0.0443(10) Uani d . . . 1 . .
O O1 0.6720(6) 0.42853(17) 0.61789(15) 0.0366(8) Uani d . . . 1 . .
O O2 1.2869(7) 0.42956(17) 0.82507(15) 0.0366(7) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.155(6) ?
C1 C2 . 1.423(6) ?
C2 C15 . 1.401(6) ?
C2 C3 . 1.412(6) ?
C3 C4 . 1.359(6) ?
C3 H3 . 0.95 ?
C4 C5 . 1.422(6) ?
C4 H4 . 0.95 ?
C5 C6 . 1.413(6) ?
C5 C14 . 1.432(5) ?
C6 C7 . 1.360(6) ?
C6 H6 . 0.95 ?
C7 C8 . 1.436(6) ?
C7 H7 . 0.95 ?
C8 C9 . 1.412(6) ?
C8 C13 . 1.420(6) ?
C9 C10 . 1.369(6) ?
C9 H9 . 0.95 ?
C10 O2 . 1.361(5) ?
C10 C11 . 1.418(6) ?
C11 C12 . 1.370(6) ?
C11 H11 . 0.95 ?
C12 O1 . 1.364(5) ?
C12 C13 . 1.440(5) ?
C13 C14 . 1.467(6) ?
C14 C15 . 1.400(6) ?
C15 H15 . 0.95 ?
C16 O1 . 1.434(4) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 O2 . 1.428(5) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 178.7(4) ?
C15 C2 C3 . . 120.8(4) ?
C15 C2 C1 . . 118.5(4) ?
C3 C2 C1 . . 120.7(4) ?
C4 C3 C2 . . 118.7(4) ?
C4 C3 H3 . . 120.7 ?
C2 C3 H3 . . 120.7 ?
C3 C4 C5 . . 122.2(4) ?
C3 C4 H4 . . 118.9 ?
C5 C4 H4 . . 118.9 ?
C6 C5 C4 . . 119.7(4) ?
C6 C5 C14 . . 120.9(4) ?
C4 C5 C14 . . 119.4(4) ?
C7 C6 C5 . . 120.6(4) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 121.5(4) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C13 . . 122.8(4) ?
C9 C8 C7 . . 117.4(4) ?
C13 C8 C7 . . 119.8(4) ?
C10 C9 C8 . . 118.9(4) ?
C10 C9 H9 . . 120.5 ?
C8 C9 H9 . . 120.5 ?
O2 C10 C9 . . 125.4(4) ?
O2 C10 C11 . . 114.1(3) ?
C9 C10 C11 . . 120.4(4) ?
C12 C11 C10 . . 120.7(3) ?
C12 C11 H11 . . 119.6 ?
C10 C11 H11 . . 119.6 ?
O1 C12 C11 . . 121.8(3) ?
O1 C12 C13 . . 116.9(3) ?
C11 C12 C13 . . 121.3(4) ?
C8 C13 C12 . . 115.7(4) ?
C8 C13 C14 . . 118.8(3) ?
C12 C13 C14 . . 125.4(4) ?
C15 C14 C5 . . 117.8(4) ?
C15 C14 C13 . . 124.0(3) ?
C5 C14 C13 . . 118.2(4) ?
C14 C15 C2 . . 121.2(4) ?
C14 C15 H15 . . 119.4 ?
C2 C15 H15 . . 119.4 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C12 O1 C16 . . 118.2(3) ?
C10 O2 C17 . . 116.5(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_rb131s
_database_code_depnum_ccdc_archive 'CCDC 2442323'
loop_
_audit_author_name
_audit_author_address
'Yongxinn Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        5,6-dimethoxyphenanthrene-3-carbonitrile
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         263.28

_chemical_melting_point          402-404

_space_group_crystal_system      monoclinic
_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                   17.1619(13)
_cell_length_b                   4.1957(3)
_cell_length_c                   17.1569(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.993(5)
_cell_angle_gamma                90
_cell_volume                     1235.22(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3928
_cell_measurement_theta_min      5.1552
_cell_measurement_theta_max      67.5768
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6935
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0943
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         67.57
_diffrn_reflns_theta_full        67.57
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
;

_reflns_number_total             2155
_reflns_number_gt                1809
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_gt          0.1944
_refine_ls_wR_factor_ref         0.2124
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_number_reflns         2155
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1541P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.528
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2018)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.08992(12) -0.2092(5) 0.50219(12) 0.0245(5) Uani d . . . 1 . .
C C2 0.11098(12) -0.0920(5) 0.57858(11) 0.0220(5) Uani d . . . 1 . .
C C3 0.06432(12) -0.1639(5) 0.64289(13) 0.0250(5) Uani d . . . 1 . .
H H3 0.018669 -0.29023 0.636859 0.03 Uiso calc U . R 1 . .
C C4 0.08644(12) -0.0471(5) 0.71418(12) 0.0247(5) Uani d . . . 1 . .
H H4 0.055191 -0.092969 0.757948 0.03 Uiso calc U . R 1 . .
C C5 0.15415(12) 0.1393(5) 0.72497(12) 0.0226(5) Uani d . . . 1 . .
C C6 0.17258(13) 0.2695(5) 0.80031(12) 0.0245(5) Uani d . . . 1 . .
H H6 0.139902 0.223904 0.843022 0.029 Uiso calc U . R 1 . .
C C7 0.23576(13) 0.4559(5) 0.81116(11) 0.0251(5) Uani d . . . 1 . .
H H7 0.24542 0.547204 0.861075 0.03 Uiso calc U . R 1 . .
C C8 0.28864(12) 0.5201(5) 0.74972(11) 0.0223(5) Uani d . . . 1 . .
C C9 0.35546(13) 0.7051(5) 0.76478(12) 0.0242(5) Uani d . . . 1 . .
H H9 0.36312 0.794346 0.815222 0.029 Uiso calc U . R 1 . .
C C10 0.41000(13) 0.7608(5) 0.70881(13) 0.0245(5) Uani d . . . 1 . .
H H10 0.454568 0.888144 0.720005 0.029 Uiso calc U . R 1 . .
C C11 0.39854(12) 0.6258(5) 0.63491(12) 0.0221(5) Uani d . . . 1 . .
C C12 0.33152(12) 0.4492(5) 0.61727(11) 0.0203(5) Uani d . . . 1 . .
C C13 0.27459(12) 0.3902(5) 0.67359(11) 0.0202(5) Uani d . . . 1 . .
C C14 0.20310(12) 0.2048(5) 0.66054(12) 0.0204(5) Uani d . . . 1 . .
C C15 0.17857(12) 0.0854(5) 0.58720(11) 0.0222(5) Uani d . . . 1 . .
H H15 0.209159 0.127744 0.542753 0.027 Uiso calc U . R 1 . .
C C16 0.30599(12) 0.5357(5) 0.48306(11) 0.0237(5) Uani d . . . 1 . .
H H16A 0.252592 0.611412 0.490393 0.036 Uiso calc U . R 1 . .
H H16B 0.309526 0.429913 0.432321 0.036 Uiso calc U . R 1 . .
H H16C 0.341929 0.717161 0.484995 0.036 Uiso calc U . R 1 . .
C C17 0.51907(12) 0.8360(6) 0.59033(12) 0.0263(6) Uani d . . . 1 . .
H H17A 0.504281 1.057649 0.600363 0.039 Uiso calc U . R 1 . .
H H17B 0.552672 0.827284 0.544771 0.039 Uiso calc U . R 1 . .
H H17C 0.547249 0.750428 0.635879 0.039 Uiso calc U . R 1 . .
N N1 0.07502(11) -0.3056(5) 0.44074(11) 0.0317(5) Uani d . . . 1 . .
O O1 0.32639(8) 0.3138(3) 0.54387(8) 0.0211(4) Uani d . . . 1 . .
O O2 0.45042(8) 0.6499(4) 0.57568(8) 0.0242(5) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.154(3) ?
C1 C2 . 1.440(3) ?
C2 C15 . 1.384(3) ?
C2 C3 . 1.407(3) ?
C3 C4 . 1.365(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.410(3) ?
C4 H4 . 0.95 ?
C5 C14 . 1.427(3) ?
C5 C6 . 1.434(3) ?
C6 C7 . 1.347(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.428(3) ?
C7 H7 . 0.95 ?
C8 C9 . 1.405(3) ?
C8 C13 . 1.432(3) ?
C9 C10 . 1.373(3) ?
C9 H9 . 0.95 ?
C10 C11 . 1.399(3) ?
C10 H10 . 0.95 ?
C11 O2 . 1.367(3) ?
C11 C12 . 1.397(3) ?
C12 O1 . 1.383(2) ?
C12 C13 . 1.408(3) ?
C13 C14 . 1.467(3) ?
C14 C15 . 1.412(3) ?
C15 H15 . 0.95 ?
C16 O1 . 1.437(2) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 O2 . 1.432(2) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 178.2(2) ?
C15 C2 C3 . . 121.25(19) ?
C15 C2 C1 . . 118.53(18) ?
C3 C2 C1 . . 120.21(19) ?
C4 C3 C2 . . 118.2(2) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 122.16(19) ?
C3 C4 H4 . . 118.9 ?
C5 C4 H4 . . 118.9 ?
C4 C5 C14 . . 120.01(19) ?
C4 C5 C6 . . 119.89(19) ?
C14 C5 C6 . . 120.1(2) ?
C7 C6 C5 . . 120.70(19) ?
C7 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C6 C7 C8 . . 121.83(19) ?
C6 C7 H7 . . 119.1 ?
C8 C7 H7 . . 119.1 ?
C9 C8 C7 . . 119.69(19) ?
C9 C8 C13 . . 120.14(19) ?
C7 C8 C13 . . 120.2(2) ?
C10 C9 C8 . . 121.98(19) ?
C10 C9 H9 . . 119.0 ?
C8 C9 H9 . . 119.0 ?
C9 C10 C11 . . 118.6(2) ?
C9 C10 H10 . . 120.7 ?
C11 C10 H10 . . 120.7 ?
O2 C11 C12 . . 115.01(18) ?
O2 C11 C10 . . 124.11(19) ?
C12 C11 C10 . . 120.88(19) ?
O1 C12 C11 . . 117.02(17) ?
O1 C12 C13 . . 121.25(18) ?
C11 C12 C13 . . 121.54(18) ?
C12 C13 C8 . . 116.82(19) ?
C12 C13 C14 . . 125.25(18) ?
C8 C13 C14 . . 117.92(18) ?
C15 C14 C5 . . 116.85(19) ?
C15 C14 C13 . . 124.05(18) ?
C5 C14 C13 . . 119.10(18) ?
C2 C15 C14 . . 121.50(18) ?
C2 C15 H15 . . 119.2 ?
C14 C15 H15 . . 119.2 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C12 O1 C16 . . 113.95(15) ?
C11 O2 C17 . . 117.04(16) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
####################################################################### 
# 
# 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_rb133s
_database_code_depnum_ccdc_archive 'CCDC 2442322'
loop_
_audit_author_name
_audit_author_address
'Yongxin Li'
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2025-04-09 deposited with the CCDC.	2025-10-02 downloaded from the CCDC.
;
_chemical_name_systematic        8,9-dimethoxybenzo[h]quinoline
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         263.28
_chemical_absolute_configuration ?

_chemical_melting_point          490-492

_space_group_crystal_system      monoclinic
_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                   6.8524(5)
_cell_length_b                   17.0457(14)
_cell_length_c                   11.0340(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.613(5)
_cell_angle_gamma                90
_cell_volume                     1277.45(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4669
_cell_measurement_theta_min      2.5922
_cell_measurement_theta_max      66.8124
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.52
_exptl_absorpt_correction_T_max  0.82

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6454
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_av_unetI/netI     0.0665
_diffrn_reflns_theta_min         4.80
_diffrn_reflns_theta_max         66.81
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
;

_reflns_number_total             4014
_reflns_number_gt                3575
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_gt          0.1355
_refine_ls_wR_factor_ref         0.1423
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_number_reflns         4014
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.226
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1339 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)

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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 -0.1258(5) 0.7108(2) 0.3251(3) 0.0299(8) Uani d . . . 1 . .
C C2 0.0584(5) 0.6760(2) 0.3751(3) 0.0289(8) Uani d . . . 1 . .
C C3 0.1914(5) 0.6531(2) 0.2937(3) 0.0305(8) Uani d . . . 1 . .
H H3 0.159938 0.660546 0.208048 0.037 Uiso calc U . R 1 . .
C C4 0.3664(5) 0.6198(2) 0.3419(3) 0.0316(8) Uani d . . . 1 . .
H H4 0.456139 0.603574 0.2882 0.038 Uiso calc U . R 1 . .
C C5 0.4172(5) 0.6090(2) 0.4684(3) 0.0279(8) Uani d . . . 1 . .
C C6 0.6010(5) 0.5732(2) 0.5161(3) 0.0296(8) Uani d . . . 1 . .
H H6 0.690377 0.557809 0.461628 0.036 Uiso calc U . R 1 . .
C C7 0.6484(5) 0.5613(2) 0.6369(4) 0.0290(8) Uani d . . . 1 . .
H H7 0.770986 0.537474 0.666241 0.035 Uiso calc U . R 1 . .
C C8 0.5186(5) 0.5836(2) 0.7222(3) 0.0269(8) Uani d . . . 1 . .
C C9 0.5676(5) 0.5683(2) 0.8485(3) 0.0271(8) Uani d . . . 1 . .
H H9 0.686803 0.541668 0.876508 0.033 Uiso calc U . R 1 . .
C C10 0.4467(5) 0.5911(2) 0.9311(3) 0.0264(8) Uani d . . . 1 . .
C C11 0.2660(5) 0.6306(2) 0.8892(3) 0.0259(8) Uani d . . . 1 . .
C C12 0.2147(5) 0.6445(2) 0.7664(3) 0.0256(8) Uani d . . . 1 . .
H H12 0.093796 0.670212 0.73911 0.031 Uiso calc U . R 1 . .
C C13 0.3387(5) 0.6214(2) 0.6800(3) 0.0260(8) Uani d . . . 1 . .
C C14 0.2855(5) 0.6331(2) 0.5499(3) 0.0253(7) Uani d . . . 1 . .
C C15 0.1031(5) 0.6668(2) 0.4996(3) 0.0262(8) Uani d . . . 1 . .
H H15 0.011535 0.682993 0.552136 0.031 Uiso calc U . R 1 . .
C C16 -0.0160(5) 0.6977(2) 0.9410(3) 0.0304(8) Uani d . . . 1 . .
H H16A 0.020486 0.744457 0.897369 0.046 Uiso calc U . R 1 . .
H H16B -0.07499 0.713752 1.013335 0.046 Uiso calc U . R 1 . .
H H16C -0.111266 0.666622 0.886917 0.046 Uiso calc U . R 1 . .
C C17 0.6604(5) 0.5384(2) 1.0989(4) 0.0355(9) Uani d . . . 1 . .
H H17A 0.656644 0.486392 1.060645 0.053 Uiso calc U . R 1 . .
H H17B 0.669931 0.532475 1.187835 0.053 Uiso calc U . R 1 . .
H H17C 0.77499 0.567408 1.078406 0.053 Uiso calc U . R 1 . .
C C18 0.3644(5) 0.2885(2) 0.3746(3) 0.0296(8) Uani d . . . 1 . .
C C19 0.5490(5) 0.3240(2) 0.4234(3) 0.0292(8) Uani d . . . 1 . .
C C20 0.6776(5) 0.3494(2) 0.3425(4) 0.0329(8) Uani d . . . 1 . .
H H20 0.644097 0.343315 0.256727 0.04 Uiso calc U . R 1 . .
C C21 0.8533(5) 0.3832(2) 0.3902(4) 0.0326(9) Uani d . . . 1 . .
H H21 0.941134 0.400908 0.336205 0.039 Uiso calc U . R 1 . .
C C22 0.9060(5) 0.3923(2) 0.5169(4) 0.0295(8) Uani d . . . 1 . .
C C23 1.0898(5) 0.4282(2) 0.5646(4) 0.0328(9) Uani d . . . 1 . .
H H23 1.177123 0.445326 0.50995 0.039 Uiso calc U . R 1 . .
C C24 1.1401(5) 0.4379(2) 0.6865(4) 0.0314(8) Uani d . . . 1 . .
H H24 1.261958 0.462155 0.716118 0.038 Uiso calc U . R 1 . .
C C25 1.0140(5) 0.4126(2) 0.7704(4) 0.0287(8) Uani d . . . 1 . .
C C26 1.0680(5) 0.4243(2) 0.8973(4) 0.0292(8) Uani d . . . 1 . .
H H26 1.187923 0.4506 0.924914 0.035 Uiso calc U . R 1 . .
C C27 0.9521(5) 0.3988(2) 0.9814(3) 0.0276(8) Uani d . . . 1 . .
C C28 0.7723(5) 0.3586(2) 0.9395(3) 0.0264(8) Uani d . . . 1 . .
C C29 0.7147(5) 0.3484(2) 0.8165(3) 0.0274(8) Uani d . . . 1 . .
H H29 0.593058 0.32316 0.789676 0.033 Uiso calc U . R 1 . .
C C30 0.8327(5) 0.3747(2) 0.7295(3) 0.0265(8) Uani d . . . 1 . .
C C31 0.7767(5) 0.3659(2) 0.5988(3) 0.0257(8) Uani d . . . 1 . .
C C32 0.5962(5) 0.3318(2) 0.5485(3) 0.0275(8) Uani d . . . 1 . .
H H32 0.506503 0.313919 0.601127 0.033 Uiso calc U . R 1 . .
C C33 0.4924(5) 0.2897(2) 0.9910(3) 0.0292(8) Uani d . . . 1 . .
H H33A 0.395741 0.32302 0.941816 0.044 Uiso calc U . R 1 . .
H H33B 0.436602 0.27061 1.062854 0.044 Uiso calc U . R 1 . .
H H33C 0.525571 0.244977 0.941844 0.044 Uiso calc U . R 1 . .
C C34 1.1738(5) 0.4484(3) 1.1469(4) 0.0370(9) Uani d . . . 1 . .
H H34A 1.28529 0.420749 1.119199 0.055 Uiso calc U . R 1 . .
H H34B 1.191697 0.450527 1.236402 0.055 Uiso calc U . R 1 . .
H H34C 1.166564 0.501795 1.11382 0.055 Uiso calc U . R 1 . .
N N1 -0.2717(4) 0.7387(2) 0.2820(3) 0.0384(8) Uani d . . . 1 . .
N N2 0.2190(4) 0.2602(2) 0.3325(3) 0.0368(8) Uani d . . . 1 . .
O O1 0.1573(3) 0.65120(15) 0.9784(2) 0.0287(6) Uani d . . . 1 . .
O O2 0.4834(3) 0.58063(16) 1.0545(2) 0.0302(6) Uani d . . . 1 . .
O O3 0.6685(3) 0.33480(15) 1.0303(2) 0.0288(6) Uani d . . . 1 . .
O O4 0.9942(3) 0.40722(14) 1.1045(2) 0.0309(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.151(5) ?
C1 C2 . 1.437(5) ?
C2 C15 . 1.377(5) ?
C2 C3 . 1.416(5) ?
C3 C4 . 1.368(5) ?
C3 H3 . 0.95 ?
C4 C5 . 1.406(5) ?
C4 H4 . 0.95 ?
C5 C14 . 1.416(5) ?
C5 C6 . 1.435(5) ?
C6 C7 . 1.345(5) ?
C6 H6 . 0.95 ?
C7 C8 . 1.429(5) ?
C7 H7 . 0.95 ?
C8 C9 . 1.414(5) ?
C8 C13 . 1.414(4) ?
C9 C10 . 1.367(5) ?
C9 H9 . 0.95 ?
C10 O2 . 1.363(4) ?
C10 C11 . 1.431(5) ?
C11 O1 . 1.357(4) ?
C11 C12 . 1.374(5) ?
C12 C13 . 1.415(5) ?
C12 H12 . 0.95 ?
C13 C14 . 1.448(5) ?
C14 C15 . 1.420(5) ?
C15 H15 . 0.95 ?
C16 O1 . 1.442(4) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 O2 . 1.440(4) ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 N2 . 1.148(5) ?
C18 C19 . 1.441(5) ?
C19 C32 . 1.381(5) ?
C19 C20 . 1.403(5) ?
C20 C21 . 1.375(5) ?
C20 H20 . 0.95 ?
C21 C22 . 1.405(5) ?
C21 H21 . 0.95 ?
C22 C31 . 1.421(5) ?
C22 C23 . 1.436(5) ?
C23 C24 . 1.353(5) ?
C23 H23 . 0.95 ?
C24 C25 . 1.415(5) ?
C24 H24 . 0.95 ?
C25 C26 . 1.414(5) ?
C25 C30 . 1.420(5) ?
C26 C27 . 1.370(5) ?
C26 H26 . 0.95 ?
C27 O4 . 1.359(4) ?
C27 C28 . 1.431(5) ?
C28 O3 . 1.365(4) ?
C28 C29 . 1.373(5) ?
C29 C30 . 1.408(5) ?
C29 H29 . 0.95 ?
C30 C31 . 1.450(5) ?
C31 C32 . 1.412(5) ?
C32 H32 . 0.95 ?
C33 O3 . 1.448(4) ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?
C34 O4 . 1.439(4) ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 178.1(4) ?
C15 C2 C3 . . 121.6(3) ?
C15 C2 C1 . . 119.9(3) ?
C3 C2 C1 . . 118.5(3) ?
C4 C3 C2 . . 118.2(3) ?
C4 C3 H3 . . 120.9 ?
C2 C3 H3 . . 120.9 ?
C3 C4 C5 . . 121.9(3) ?
C3 C4 H4 . . 119.0 ?
C5 C4 H4 . . 119.0 ?
C4 C5 C14 . . 119.8(3) ?
C4 C5 C6 . . 120.6(3) ?
C14 C5 C6 . . 119.5(3) ?
C7 C6 C5 . . 120.8(3) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 121.5(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C9 C8 C13 . . 119.4(3) ?
C9 C8 C7 . . 120.9(3) ?
C13 C8 C7 . . 119.7(3) ?
C10 C9 C8 . . 121.3(3) ?
C10 C9 H9 . . 119.3 ?
C8 C9 H9 . . 119.3 ?
O2 C10 C9 . . 125.5(3) ?
O2 C10 C11 . . 115.0(3) ?
C9 C10 C11 . . 119.5(3) ?
O1 C11 C12 . . 125.2(3) ?
O1 C11 C10 . . 114.9(3) ?
C12 C11 C10 . . 119.9(3) ?
C11 C12 C13 . . 121.2(3) ?
C11 C12 H12 . . 119.4 ?
C13 C12 H12 . . 119.4 ?
C12 C13 C8 . . 118.7(3) ?
C12 C13 C14 . . 122.4(3) ?
C8 C13 C14 . . 118.9(3) ?
C5 C14 C15 . . 118.1(3) ?
C5 C14 C13 . . 119.5(3) ?
C15 C14 C13 . . 122.4(3) ?
C2 C15 C14 . . 120.3(3) ?
C2 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
O1 C16 H16A . . 109.5 ?
O1 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
O1 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
O2 C17 H17A . . 109.5 ?
O2 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O2 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
N2 C18 C19 . . 178.1(4) ?
C32 C19 C20 . . 121.5(3) ?
C32 C19 C18 . . 119.4(3) ?
C20 C19 C18 . . 119.1(3) ?
C21 C20 C19 . . 118.6(3) ?
C21 C20 H20 . . 120.7 ?
C19 C20 H20 . . 120.7 ?
C20 C21 C22 . . 121.5(3) ?
C20 C21 H21 . . 119.2 ?
C22 C21 H21 . . 119.2 ?
C21 C22 C31 . . 119.9(3) ?
C21 C22 C23 . . 120.6(3) ?
C31 C22 C23 . . 119.5(3) ?
C24 C23 C22 . . 120.8(3) ?
C24 C23 H23 . . 119.6 ?
C22 C23 H23 . . 119.6 ?
C23 C24 C25 . . 121.0(3) ?
C23 C24 H24 . . 119.5 ?
C25 C24 H24 . . 119.5 ?
C24 C25 C26 . . 120.2(3) ?
C24 C25 C30 . . 121.0(3) ?
C26 C25 C30 . . 118.8(3) ?
C27 C26 C25 . . 121.8(3) ?
C27 C26 H26 . . 119.1 ?
C25 C26 H26 . . 119.1 ?
O4 C27 C26 . . 125.3(3) ?
O4 C27 C28 . . 115.7(3) ?
C26 C27 C28 . . 119.0(3) ?
O3 C28 C29 . . 125.3(3) ?
O3 C28 C27 . . 114.5(3) ?
C29 C28 C27 . . 120.1(3) ?
C28 C29 C30 . . 121.2(3) ?
C28 C29 H29 . . 119.4 ?
C30 C29 H29 . . 119.4 ?
C29 C30 C25 . . 119.0(3) ?
C29 C30 C31 . . 123.0(3) ?
C25 C30 C31 . . 117.9(3) ?
C32 C31 C22 . . 117.9(3) ?
C32 C31 C30 . . 122.4(3) ?
C22 C31 C30 . . 119.7(3) ?
C19 C32 C31 . . 120.6(3) ?
C19 C32 H32 . . 119.7 ?
C31 C32 H32 . . 119.7 ?
O3 C33 H33A . . 109.5 ?
O3 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
O3 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
O4 C34 H34A . . 109.5 ?
O4 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
O4 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C11 O1 C16 . . 116.5(3) ?
C10 O2 C17 . . 116.2(3) ?
C28 O3 C33 . . 115.7(3) ?
C27 O4 C34 . . 115.8(3) ?


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
