# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_ch1
_database_code_depnum_ccdc_archive 'CCDC 2041954'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H22 N2 O2'
_chemical_formula_weight         430.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1585(3)
_cell_length_b                   10.7347(4)
_cell_length_c                   11.6344(5)
_cell_angle_alpha                93.7241(17)
_cell_angle_beta                 98.7149(18)
_cell_angle_gamma                99.1029(17)
_cell_volume                     1111.73(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2081
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      20.59

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.980
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15039
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.778
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3903
_reflns_number_gt                2286
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0965P)²+0.4904P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3903
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0654
_refine_ls_wR_factor_ref         0.2109
_refine_ls_wR_factor_gt          0.1776
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.4944(3) 0.2616(3) 0.7574(2) 0.0415(7) Uani 1 1 d . . . . .
C2 C 0.6092(3) 0.2715(3) 0.8477(2) 0.0394(7) Uani 1 1 d . . . . .
C3 C 0.6448(3) 0.1575(3) 0.8949(2) 0.0397(7) Uani 1 1 d . . . . .
C4 C 0.7564(3) 0.1606(3) 0.9937(3) 0.0508(8) Uani 1 1 d . . . . .
H4 H 0.8115 0.2378 1.0280 0.061 Uiso 1 1 calc R U . . .
C5 C 0.7839(4) 0.0505(3) 1.0393(3) 0.0608(9) Uani 1 1 d . . . . .
H5 H 0.8576 0.0538 1.1045 0.073 Uiso 1 1 calc R U . . .
C6 C 0.7041(4) -0.0647(3) 0.9900(3) 0.0611(9) Uani 1 1 d . . . . .
H6 H 0.7230 -0.1383 1.0231 0.073 Uiso 1 1 calc R U . . .
C7 C 0.5969(4) -0.0725(3) 0.8927(3) 0.0523(8) Uani 1 1 d . . . . .
H7 H 0.5449 -0.1511 0.8590 0.063 Uiso 1 1 calc R U . . .
C8 C 0.5660(3) 0.0389(3) 0.8440(2) 0.0416(7) Uani 1 1 d . . . . .
C9 C 0.4498(3) 0.0295(3) 0.7419(3) 0.0474(8) Uani 1 1 d . . . . .
C10 C 0.3077(3) 0.1420(3) 0.6005(3) 0.0488(8) Uani 1 1 d . . . . .
C11 C 0.1612(3) 0.1485(3) 0.6177(3) 0.0480(8) Uani 1 1 d . . . . .
C12 C -0.0142(4) 0.1540(4) 0.7367(4) 0.0710(11) Uani 1 1 d . . . . .
H12 H -0.0395 0.1542 0.8112 0.085 Uiso 1 1 calc R U . . .
C13 C -0.1263(4) 0.1602(4) 0.6452(4) 0.0722(11) Uani 1 1 d . . . . .
H13 H -0.2233 0.1638 0.6584 0.087 Uiso 1 1 calc R U . . .
C14 C -0.0934(4) 0.1611(3) 0.5363(3) 0.0592(10) Uani 1 1 d . . . . .
H14 H -0.1686 0.1643 0.4737 0.071 Uiso 1 1 calc R U . . .
C15 C 0.0531(4) 0.1572(3) 0.5163(3) 0.0499(8) Uani 1 1 d . . . . .
C16 C 0.0958(4) 0.1606(3) 0.4065(3) 0.0658(10) Uani 1 1 d . . . . .
H16 H 0.0256 0.1668 0.3413 0.079 Uiso 1 1 calc R U . . .
C17 C 0.2428(5) 0.1548(4) 0.3941(3) 0.0748(11) Uani 1 1 d . . . . .
H17 H 0.2726 0.1578 0.3212 0.090 Uiso 1 1 calc R U . . .
C18 C 0.3459(4) 0.1444(3) 0.4939(3) 0.0546(9) Uani 1 1 d . . . . .
H18 H 0.4443 0.1390 0.4857 0.066 Uiso 1 1 calc R U . . .
C19 C 0.4389(3) 0.3697(3) 0.7135(3) 0.0443(8) Uani 1 1 d . . . . .
C20 C 0.3863(3) 0.4594(3) 0.6835(3) 0.0472(8) Uani 1 1 d . . . . .
C21 C 0.3149(4) 0.5651(3) 0.6412(3) 0.0535(9) Uani 1 1 d . . . . .
C22 C 0.1568(5) 0.5436(6) 0.6578(6) 0.144(3) Uani 1 1 d . . . . .
H22A H 0.1516 0.5320 0.7383 0.217 Uiso 1 1 calc R U . . .
H22B H 0.1039 0.4692 0.6098 0.217 Uiso 1 1 calc R U . . .
H22C H 0.1121 0.6155 0.6361 0.217 Uiso 1 1 calc R U . . .
C23 C 0.3327(7) 0.5793(6) 0.5201(4) 0.153(3) Uani 1 1 d . . . . .
H23A H 0.2890 0.6501 0.4938 0.229 Uiso 1 1 calc R U . . .
H23B H 0.2834 0.5036 0.4723 0.229 Uiso 1 1 calc R U . . .
H23C H 0.4374 0.5934 0.5144 0.229 Uiso 1 1 calc R U . . .
C24 C 0.6950(3) 0.3988(3) 0.8928(3) 0.0406(7) Uani 1 1 d . . . . .
C25 C 0.7931(4) 0.4617(3) 0.8275(3) 0.0590(9) Uani 1 1 d . . . . .
H25 H 0.8049 0.4232 0.7563 0.071 Uiso 1 1 calc R U . . .
C26 C 0.8733(4) 0.5801(3) 0.8663(4) 0.0722(11) Uani 1 1 d . . . . .
H26 H 0.9390 0.6208 0.8216 0.087 Uiso 1 1 calc R U . . .
C27 C 0.8569(4) 0.6379(3) 0.9698(3) 0.0645(10) Uani 1 1 d . . . . .
H27 H 0.9113 0.7181 0.9958 0.077 Uiso 1 1 calc R U . . .
C28 C 0.7613(4) 0.5786(3) 1.0353(3) 0.0670(10) Uani 1 1 d . . . . .
H28 H 0.7500 0.6185 1.1060 0.080 Uiso 1 1 calc R U . . .
C29 C 0.6805(4) 0.4591(3) 0.9976(3) 0.0556(9) Uani 1 1 d . . . . .
H29 H 0.6158 0.4191 1.0435 0.067 Uiso 1 1 calc R U . . .
N1 N 0.4203(3) 0.1428(2) 0.7034(2) 0.0472(7) Uani 1 1 d . . . . .
N2 N 0.1238(3) 0.1479(3) 0.7276(2) 0.0540(7) Uani 1 1 d . . . . .
O1 O 0.3796(3) -0.0708(2) 0.6902(2) 0.0681(7) Uani 1 1 d . . . . .
O2 O 0.3874(7) 0.6728(3) 0.7132(4) 0.198(3) Uani 1 1 d . . . . .
H2 H 0.4006 0.7328 0.6736 0.296 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
C1 C2 1.355(4) . ?
C1 N1 1.405(4) . ?
C1 C19 1.432(4) . ?
C2 C3 1.437(4) . ?
C2 C24 1.484(4) . ?
C3 C8 1.405(4) . ?
C3 C4 1.413(4) . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.370(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.406(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.457(4) . ?
C9 O1 1.231(3) . ?
C9 N1 1.375(4) . ?
C10 C18 1.339(4) . ?
C10 C11 1.399(4) . ?
C10 N1 1.455(4) . ?
C11 N2 1.372(4) . ?
C11 C15 1.439(4) . ?
C12 N2 1.296(4) . ?
C12 C13 1.376(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.403(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.394(5) . ?
C16 C17 1.386(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.404(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.192(4) . ?
C20 C21 1.472(4) . ?
C21 O2 1.393(4) . ?
C21 C23 1.458(5) . ?
C21 C22 1.473(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.378(4) . ?
C24 C25 1.387(4) . ?
C25 C26 1.375(5) . ?
C25 H25 0.9300 . ?
C26 C27 1.357(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.358(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.383(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
O2 H2 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 121.2(3) . . ?
C2 C1 C19 122.6(3) . . ?
N1 C1 C19 116.2(2) . . ?
C1 C2 C3 118.5(3) . . ?
C1 C2 C24 119.0(3) . . ?
C3 C2 C24 122.5(2) . . ?
C8 C3 C4 118.2(3) . . ?
C8 C3 C2 120.1(2) . . ?
C4 C3 C2 121.7(3) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C3 C8 C7 120.1(3) . . ?
C3 C8 C9 120.7(3) . . ?
C7 C8 C9 119.1(3) . . ?
O1 C9 N1 119.8(3) . . ?
O1 C9 C8 124.5(3) . . ?
N1 C9 C8 115.7(3) . . ?
C18 C10 C11 121.3(3) . . ?
C18 C10 N1 120.8(3) . . ?
C11 C10 N1 117.7(3) . . ?
N2 C11 C10 120.8(3) . . ?
N2 C11 C15 121.9(3) . . ?
C10 C11 C15 117.3(3) . . ?
N2 C12 C13 125.3(4) . . ?
N2 C12 H12 117.4 . . ?
C13 C12 H12 117.4 . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 123.8(3) . . ?
C16 C15 C11 120.3(3) . . ?
C14 C15 C11 115.9(3) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 118.6(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C10 C18 C17 122.3(3) . . ?
C10 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
C20 C19 C1 175.1(3) . . ?
C19 C20 C21 176.6(3) . . ?
O2 C21 C23 110.8(4) . . ?
O2 C21 C20 106.2(3) . . ?
C23 C21 C20 109.8(3) . . ?
O2 C21 C22 107.5(5) . . ?
C23 C21 C22 113.0(4) . . ?
C20 C21 C22 109.3(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 117.7(3) . . ?
C29 C24 C2 122.7(3) . . ?
C25 C24 C2 119.6(3) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C27 C26 C25 120.2(3) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C26 C27 C28 120.0(3) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C27 C28 C29 120.4(3) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 120.6(3) . . ?
C24 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C9 N1 C1 123.6(2) . . ?
C9 N1 C10 119.2(2) . . ?
C1 N1 C10 117.2(2) . . ?
C12 N2 C11 117.3(3) . . ?
C21 O2 H2 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -5.9(4) . . . . ?
C19 C1 C2 C3 172.4(3) . . . . ?
N1 C1 C2 C24 173.0(2) . . . . ?
C19 C1 C2 C24 -8.7(4) . . . . ?
C1 C2 C3 C8 2.9(4) . . . . ?
C24 C2 C3 C8 -175.9(3) . . . . ?
C1 C2 C3 C4 -175.8(3) . . . . ?
C24 C2 C3 C4 5.3(4) . . . . ?
C8 C3 C4 C5 -1.3(4) . . . . ?
C2 C3 C4 C5 177.5(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C8 -1.3(5) . . . . ?
C4 C3 C8 C7 1.2(4) . . . . ?
C2 C3 C8 C7 -177.7(3) . . . . ?
C4 C3 C8 C9 -179.9(3) . . . . ?
C2 C3 C8 C9 1.3(4) . . . . ?
C6 C7 C8 C3 0.1(5) . . . . ?
C6 C7 C8 C9 -178.8(3) . . . . ?
C3 C8 C9 O1 177.4(3) . . . . ?
C7 C8 C9 O1 -3.6(5) . . . . ?
C3 C8 C9 N1 -2.5(4) . . . . ?
C7 C8 C9 N1 176.5(3) . . . . ?
C18 C10 C11 N2 -179.0(3) . . . . ?
N1 C10 C11 N2 -3.9(4) . . . . ?
C18 C10 C11 C15 0.4(4) . . . . ?
N1 C10 C11 C15 175.5(2) . . . . ?
N2 C12 C13 C14 -0.5(6) . . . . ?
C12 C13 C14 C15 -0.7(5) . . . . ?
C13 C14 C15 C16 -178.6(3) . . . . ?
C13 C14 C15 C11 1.8(5) . . . . ?
N2 C11 C15 C16 178.5(3) . . . . ?
C10 C11 C15 C16 -0.9(4) . . . . ?
N2 C11 C15 C14 -1.9(4) . . . . ?
C10 C11 C15 C14 178.8(3) . . . . ?
C14 C15 C16 C17 -179.2(3) . . . . ?
C11 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 0.6(5) . . . . ?
C11 C10 C18 C17 0.6(5) . . . . ?
N1 C10 C18 C17 -174.3(3) . . . . ?
C16 C17 C18 C10 -1.1(5) . . . . ?
C1 C2 C24 C29 106.5(4) . . . . ?
C3 C2 C24 C29 -74.6(4) . . . . ?
C1 C2 C24 C25 -72.8(4) . . . . ?
C3 C2 C24 C25 106.1(3) . . . . ?
C29 C24 C25 C26 0.1(5) . . . . ?
C2 C24 C25 C26 179.5(3) . . . . ?
C24 C25 C26 C27 -0.3(6) . . . . ?
C25 C26 C27 C28 0.1(6) . . . . ?
C26 C27 C28 C29 0.3(6) . . . . ?
C25 C24 C29 C28 0.3(5) . . . . ?
C2 C24 C29 C28 -179.1(3) . . . . ?
C27 C28 C29 C24 -0.4(5) . . . . ?
O1 C9 N1 C1 179.6(3) . . . . ?
C8 C9 N1 C1 -0.4(4) . . . . ?
O1 C9 N1 C10 -1.0(4) . . . . ?
C8 C9 N1 C10 178.9(3) . . . . ?
C2 C1 N1 C9 4.8(4) . . . . ?
C19 C1 N1 C9 -173.6(3) . . . . ?
C2 C1 N1 C10 -174.5(3) . . . . ?
C19 C1 N1 C10 7.0(4) . . . . ?
C18 C10 N1 C9 -91.5(4) . . . . ?
C11 C10 N1 C9 93.4(3) . . . . ?
C18 C10 N1 C1 87.8(4) . . . . ?
C11 C10 N1 C1 -87.3(3) . . . . ?
C13 C12 N2 C11 0.4(5) . . . . ?
C10 C11 N2 C12 -179.9(3) . . . . ?
C15 C11 N2 C12 0.8(4) . . . . ?

_refine_diff_density_max         0.518
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_ch5
_database_code_depnum_ccdc_archive 'CCDC 2041960'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H22 N2 O3'
_chemical_formula_weight         446.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.7888(12)
_cell_length_b                   10.0222(4)
_cell_length_c                   12.1293(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2284.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2190
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      22.17

_exptl_crystal_description       Square
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8565
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_point_group_measured_fraction_full 0.819
_reflns_number_total             3300
_reflns_number_gt                2636
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.558
_reflns_Friedel_fraction_max     0.619
_reflns_Friedel_fraction_full    0.619

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0803P)²+0.6130P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3300
_refine_ls_number_parameters     309
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1438
_refine_ls_wR_factor_gt          0.1317
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000

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
C1 C 0.7819(2) -0.1187(4) 0.2105(4) 0.0417(11) Uani 1 1 d . . . . .
C2 C 0.8099(3) -0.2478(4) 0.1784(4) 0.0423(11) Uani 1 1 d . . . . .
C3 C 0.7655(3) -0.3523(5) 0.1414(4) 0.0472(12) Uani 1 1 d . . . . .
H3 H 0.7166 -0.3389 0.1381 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7929(3) -0.4713(5) 0.1109(4) 0.0495(13) Uani 1 1 d . . . . .
C5 C 0.8668(3) -0.4924(5) 0.1147(5) 0.0632(16) Uani 1 1 d . . . . .
H5 H 0.8855 -0.5746 0.0941 0.076 Uiso 1 1 calc R U . . .
C6 C 0.9106(3) -0.3936(4) 0.1484(5) 0.0591(15) Uani 1 1 d . . . . .
H6 H 0.9595 -0.4081 0.1494 0.071 Uiso 1 1 calc R U . . .
C7 C 0.8836(2) -0.2694(4) 0.1819(4) 0.0440(11) Uani 1 1 d . . . . .
C8 C 0.9327(3) -0.1652(4) 0.2155(5) 0.0462(12) Uani 1 1 d . . . . .
C9 C 0.8284(2) -0.0241(4) 0.2455(4) 0.0427(12) Uani 1 1 d . . . . .
C10 C 0.9633(3) 0.0952(5) 0.3829(5) 0.0554(14) Uani 1 1 d . . . . .
H10 H 0.9458 0.0413 0.4392 0.066 Uiso 1 1 calc R U . . .
C11 C 0.9485(2) 0.0657(4) 0.2767(5) 0.0480(13) Uani 1 1 d . . . . .
C12 C 0.9717(2) 0.1465(5) 0.1890(5) 0.0477(13) Uani 1 1 d . . . . .
C13 C 0.9748(3) 0.1968(6) 0.0057(6) 0.0662(16) Uani 1 1 d . . . . .
H13 H 0.9611 0.1766 -0.0660 0.079 Uiso 1 1 calc R U . . .
C14 C 1.0164(3) 0.3115(6) 0.0225(6) 0.0687(17) Uani 1 1 d . . . . .
H14 H 1.0307 0.3646 -0.0363 0.082 Uiso 1 1 calc R U . . .
C15 C 1.0350(3) 0.3422(5) 0.1285(6) 0.0631(17) Uani 1 1 d . . . . .
H15 H 1.0628 0.4172 0.1420 0.076 Uiso 1 1 calc R U . . .
C16 C 1.0131(2) 0.2631(4) 0.2162(5) 0.0499(13) Uani 1 1 d . . . . .
C17 C 1.0266(3) 0.2904(6) 0.3281(6) 0.0658(16) Uani 1 1 d . . . . .
H17 H 1.0512 0.3678 0.3465 0.079 Uiso 1 1 calc R U . . .
C18 C 1.0054(3) 0.2088(6) 0.4086(6) 0.0733(18) Uani 1 1 d . . . . .
H18 H 1.0182 0.2262 0.4813 0.088 Uiso 1 1 calc R U . . .
C19 C 0.8061(2) 0.1060(4) 0.2810(5) 0.0472(12) Uani 1 1 d . . . . .
C20 C 0.7900(3) 0.2127(5) 0.3174(5) 0.0491(12) Uani 1 1 d . . . . .
C21 C 0.7707(3) 0.3380(4) 0.3650(5) 0.0493(13) Uani 1 1 d . . . . .
C22 C 0.8210(3) 0.4353(5) 0.3836(5) 0.0635(16) Uani 1 1 d . . . . .
H22 H 0.8684 0.4217 0.3646 0.076 Uiso 1 1 calc R U . . .
C23 C 0.7995(4) 0.5530(5) 0.4309(5) 0.0757(19) Uani 1 1 d . . . . .
H23 H 0.8332 0.6194 0.4428 0.091 Uiso 1 1 calc R U . . .
C24 C 0.7318(5) 0.5759(6) 0.4605(5) 0.077(2) Uani 1 1 d . . . . .
H24 H 0.7192 0.6561 0.4939 0.092 Uiso 1 1 calc R U . . .
C25 C 0.6818(4) 0.4804(7) 0.4411(6) 0.085(2) Uani 1 1 d . . . . .
H25 H 0.6345 0.4959 0.4597 0.102 Uiso 1 1 calc R U . . .
C26 C 0.7012(3) 0.3618(6) 0.3942(6) 0.0749(19) Uani 1 1 d . . . . .
H26 H 0.6669 0.2966 0.3818 0.090 Uiso 1 1 calc R U . . .
C27 C 0.7030(2) -0.0899(4) 0.2034(4) 0.0460(12) Uani 1 1 d . . . . .
H27A H 0.6964 0.0060 0.2001 0.055 Uiso 1 1 calc R U . . .
H27B H 0.6850 -0.1272 0.1352 0.055 Uiso 1 1 calc R U . . .
C28 C 0.6598(2) -0.1434(5) 0.2966(5) 0.0556(14) Uani 1 1 d . . . . .
H28A H 0.6654 -0.2395 0.3001 0.067 Uiso 1 1 calc R U . . .
H28B H 0.6770 -0.1061 0.3654 0.067 Uiso 1 1 calc R U . . .
C29 C 0.6785(3) -0.5650(6) 0.0772(7) 0.094(2) Uani 1 1 d . . . . .
H29A H 0.6629 -0.5397 0.1496 0.141 Uiso 1 1 calc R U . . .
H29B H 0.6567 -0.6482 0.0570 0.141 Uiso 1 1 calc R U . . .
H29C H 0.6650 -0.4974 0.0253 0.141 Uiso 1 1 calc R U . . .
N1 N 0.90207(19) -0.0460(3) 0.2485(4) 0.0466(11) Uani 1 1 d . . . . .
N2 N 0.9540(2) 0.1164(4) 0.0847(4) 0.0518(11) Uani 1 1 d . . . . .
O1 O 0.7550(2) -0.5798(4) 0.0769(4) 0.0730(13) Uani 1 1 d . . . . .
O2 O 0.99865(17) -0.1768(3) 0.2169(4) 0.0635(10) Uani 1 1 d . . . . .
O3 O 0.58657(17) -0.1119(3) 0.2837(4) 0.0655(11) Uani 1 1 d . . . . .
H3A H 0.5665 -0.1725 0.2506 0.098 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
C1 C9 1.357(6) . ?
C1 C2 1.450(6) . ?
C1 C27 1.512(6) . ?
C2 C7 1.402(6) . ?
C2 C3 1.411(7) . ?
C3 C4 1.352(7) . ?
C3 H3 0.9300 . ?
C4 O1 1.363(6) . ?
C4 C5 1.404(7) . ?
C5 C6 1.352(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.453(6) . ?
C8 O2 1.244(5) . ?
C8 N1 1.385(6) . ?
C9 N1 1.402(6) . ?
C9 C19 1.436(6) . ?
C10 C11 1.351(8) . ?
C10 C18 1.421(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.406(7) . ?
C11 N1 1.460(6) . ?
C12 N2 1.343(7) . ?
C12 C16 1.442(6) . ?
C13 N2 1.311(7) . ?
C13 C14 1.405(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.367(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.389(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.407(9) . ?
C17 C18 1.335(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.195(6) . ?
C20 C21 1.429(7) . ?
C21 C22 1.377(7) . ?
C21 C26 1.375(8) . ?
C22 C23 1.372(8) . ?
C22 H22 0.9300 . ?
C23 C24 1.341(9) . ?
C23 H23 0.9300 . ?
C24 C25 1.362(10) . ?
C24 H24 0.9300 . ?
C25 C26 1.367(8) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.491(7) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O3 1.420(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 O1 1.446(7) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
O3 H3A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 118.3(4) . . ?
C9 C1 C27 121.0(4) . . ?
C2 C1 C27 120.7(4) . . ?
C7 C2 C3 118.5(4) . . ?
C7 C2 C1 119.2(4) . . ?
C3 C2 C1 122.2(4) . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 O1 126.0(4) . . ?
C3 C4 C5 120.0(4) . . ?
O1 C4 C5 114.0(4) . . ?
C6 C5 C4 120.2(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.0(5) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 119.1(4) . . ?
C2 C7 C8 121.7(4) . . ?
C6 C7 C8 119.2(4) . . ?
O2 C8 N1 119.4(4) . . ?
O2 C8 C7 124.7(4) . . ?
N1 C8 C7 115.9(4) . . ?
C1 C9 N1 122.3(4) . . ?
C1 C9 C19 122.7(4) . . ?
N1 C9 C19 115.0(4) . . ?
C11 C10 C18 119.9(6) . . ?
C11 C10 H10 120.0 . . ?
C18 C10 H10 120.0 . . ?
C10 C11 C12 122.1(5) . . ?
C10 C11 N1 120.9(5) . . ?
C12 C11 N1 116.8(5) . . ?
N2 C12 C11 120.4(4) . . ?
N2 C12 C16 122.1(5) . . ?
C11 C12 C16 117.5(5) . . ?
N2 C13 C14 124.3(6) . . ?
N2 C13 H13 117.9 . . ?
C14 C13 H13 117.9 . . ?
C15 C14 C13 117.6(6) . . ?
C15 C14 H14 121.2 . . ?
C13 C14 H14 121.2 . . ?
C14 C15 C16 121.0(5) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C17 125.0(5) . . ?
C15 C16 C12 116.6(5) . . ?
C17 C16 C12 118.4(5) . . ?
C18 C17 C16 122.2(5) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C17 C18 C10 119.8(6) . . ?
C17 C18 H18 120.1 . . ?
C10 C18 H18 120.1 . . ?
C20 C19 C9 175.3(6) . . ?
C19 C20 C21 177.8(6) . . ?
C22 C21 C26 119.2(5) . . ?
C22 C21 C20 121.0(5) . . ?
C26 C21 C20 119.9(5) . . ?
C23 C22 C21 118.4(6) . . ?
C23 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
C24 C23 C22 122.6(6) . . ?
C24 C23 H23 118.7 . . ?
C22 C23 H23 118.7 . . ?
C23 C24 C25 119.2(6) . . ?
C23 C24 H24 120.4 . . ?
C25 C24 H24 120.4 . . ?
C24 C25 C26 119.9(6) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 120.8(6) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
C28 C27 C1 115.0(4) . . ?
C28 C27 H27A 108.5 . . ?
C1 C27 H27A 108.5 . . ?
C28 C27 H27B 108.5 . . ?
C1 C27 H27B 108.5 . . ?
H27A C27 H27B 107.5 . . ?
O3 C28 C27 111.4(5) . . ?
O3 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
O3 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
O1 C29 H29A 109.5 . . ?
O1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C8 N1 C9 122.6(4) . . ?
C8 N1 C11 118.7(4) . . ?
C9 N1 C11 118.5(3) . . ?
C13 N2 C12 118.4(5) . . ?
C4 O1 C29 115.9(4) . . ?
C28 O3 H3A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C7 -1.7(7) . . . . ?
C27 C1 C2 C7 177.5(5) . . . . ?
C9 C1 C2 C3 179.7(5) . . . . ?
C27 C1 C2 C3 -1.1(7) . . . . ?
C7 C2 C3 C4 0.6(8) . . . . ?
C1 C2 C3 C4 179.3(5) . . . . ?
C2 C3 C4 O1 178.1(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 -0.4(9) . . . . ?
O1 C4 C5 C6 -179.1(5) . . . . ?
C4 C5 C6 C7 1.1(9) . . . . ?
C3 C2 C7 C6 0.1(7) . . . . ?
C1 C2 C7 C6 -178.6(5) . . . . ?
C3 C2 C7 C8 177.9(5) . . . . ?
C1 C2 C7 C8 -0.8(7) . . . . ?
C5 C6 C7 C2 -1.0(8) . . . . ?
C5 C6 C7 C8 -178.9(5) . . . . ?
C2 C7 C8 O2 -177.6(5) . . . . ?
C6 C7 C8 O2 0.2(8) . . . . ?
C2 C7 C8 N1 2.9(7) . . . . ?
C6 C7 C8 N1 -179.3(5) . . . . ?
C2 C1 C9 N1 2.0(7) . . . . ?
C27 C1 C9 N1 -177.2(4) . . . . ?
C2 C1 C9 C19 -178.8(5) . . . . ?
C27 C1 C9 C19 2.0(8) . . . . ?
C18 C10 C11 C12 -2.1(7) . . . . ?
C18 C10 C11 N1 -176.5(4) . . . . ?
C10 C11 C12 N2 -177.8(5) . . . . ?
N1 C11 C12 N2 -3.1(6) . . . . ?
C10 C11 C12 C16 0.7(6) . . . . ?
N1 C11 C12 C16 175.4(4) . . . . ?
N2 C13 C14 C15 -1.3(9) . . . . ?
C13 C14 C15 C16 -0.5(8) . . . . ?
C14 C15 C16 C17 -176.7(5) . . . . ?
C14 C15 C16 C12 1.6(7) . . . . ?
N2 C12 C16 C15 -1.1(7) . . . . ?
C11 C12 C16 C15 -179.5(4) . . . . ?
N2 C12 C16 C17 177.3(5) . . . . ?
C11 C12 C16 C17 -1.2(6) . . . . ?
C15 C16 C17 C18 -178.5(5) . . . . ?
C12 C16 C17 C18 3.3(8) . . . . ?
C16 C17 C18 C10 -4.7(9) . . . . ?
C11 C10 C18 C17 4.1(8) . . . . ?
C26 C21 C22 C23 0.0(8) . . . . ?
C20 C21 C22 C23 -179.2(5) . . . . ?
C21 C22 C23 C24 0.7(9) . . . . ?
C22 C23 C24 C25 -1.5(10) . . . . ?
C23 C24 C25 C26 1.4(11) . . . . ?
C24 C25 C26 C21 -0.7(11) . . . . ?
C22 C21 C26 C25 -0.1(9) . . . . ?
C20 C21 C26 C25 179.2(6) . . . . ?
C9 C1 C27 C28 -100.9(6) . . . . ?
C2 C1 C27 C28 79.9(6) . . . . ?
C1 C27 C28 O3 179.9(4) . . . . ?
O2 C8 N1 C9 177.8(5) . . . . ?
C7 C8 N1 C9 -2.7(7) . . . . ?
O2 C8 N1 C11 4.3(7) . . . . ?
C7 C8 N1 C11 -176.2(4) . . . . ?
C1 C9 N1 C8 0.3(8) . . . . ?
C19 C9 N1 C8 -179.0(5) . . . . ?
C1 C9 N1 C11 173.8(5) . . . . ?
C19 C9 N1 C11 -5.4(7) . . . . ?
C10 C11 N1 C8 -100.2(6) . . . . ?
C12 C11 N1 C8 85.1(5) . . . . ?
C10 C11 N1 C9 86.1(6) . . . . ?
C12 C11 N1 C9 -88.7(5) . . . . ?
C14 C13 N2 C12 1.8(8) . . . . ?
C11 C12 N2 C13 177.9(5) . . . . ?
C16 C12 N2 C13 -0.5(7) . . . . ?
C3 C4 O1 C29 -1.8(9) . . . . ?
C5 C4 O1 C29 176.9(6) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_ch3
_database_code_depnum_ccdc_archive 'CCDC 2041961'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H19 Br N2 O2'
_chemical_formula_weight         495.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3549(3)
_cell_length_b                   10.5712(4)
_cell_length_c                   18.7259(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.0039(14)
_cell_angle_gamma                90
_cell_volume                     2244.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9060
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.30

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.860
_shelx_estimated_absorpt_T_min   0.605
_shelx_estimated_absorpt_T_max   0.755
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27377
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.796
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3966
_reflns_number_gt                3207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+1.8119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3966
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0879
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.64279(3) 1.48638(3) 0.16204(2) 0.05775(13) Uani 1 1 d . . . . .
C1 C 0.3965(2) 1.2122(2) 0.10443(12) 0.0348(5) Uani 1 1 d . . . . .
C2 C 0.4617(2) 1.3054(2) 0.14127(13) 0.0403(6) Uani 1 1 d . . . . .
H2 H 0.4442 1.3268 0.1877 0.048 Uiso 1 1 calc R U . . .
C3 C 0.5512(2) 1.3649(2) 0.10904(14) 0.0426(6) Uani 1 1 d . . . . .
C4 C 0.5785(2) 1.3348(3) 0.03949(15) 0.0486(7) Uani 1 1 d . . . . .
H4 H 0.6399 1.3759 0.0181 0.058 Uiso 1 1 calc R U . . .
C5 C 0.5140(2) 1.2442(3) 0.00283(13) 0.0443(6) Uani 1 1 d . . . . .
H5 H 0.5322 1.2246 -0.0437 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4210(2) 1.1801(2) 0.03392(12) 0.0345(5) Uani 1 1 d . . . . .
C7 C 0.3521(2) 1.0836(2) -0.00323(12) 0.0340(5) Uani 1 1 d . . . . .
C8 C 0.2707(2) 1.0201(2) 0.03296(12) 0.0331(5) Uani 1 1 d . . . . .
C9 C 0.3063(2) 1.1445(2) 0.14246(12) 0.0354(6) Uani 1 1 d . . . . .
C10 C 0.3645(2) 1.0598(2) -0.08205(12) 0.0364(6) Uani 1 1 d . . . . .
H10A H 0.3314 0.9778 -0.0948 0.044 Uiso 1 1 calc R U . . .
H10B H 0.4474 1.0591 -0.0923 0.044 Uiso 1 1 calc R U . . .
C11 C 0.3013(2) 1.1616(2) -0.12612(12) 0.0377(6) Uani 1 1 d . . . . .
H11A H 0.2196 1.1668 -0.1137 0.045 Uiso 1 1 calc R U . . .
H11B H 0.3383 1.2430 -0.1164 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1968(2) 0.9225(2) 0.00285(12) 0.0373(6) Uani 1 1 d . . . . .
C13 C 0.1320(2) 0.8397(2) -0.01783(13) 0.0410(6) Uani 1 1 d . . . . .
C14 C 0.0489(2) 0.7426(2) -0.03827(13) 0.0406(6) Uani 1 1 d . . . . .
C15 C 0.0661(3) 0.6635(3) -0.09513(15) 0.0620(9) Uani 1 1 d . . . . .
H15 H 0.1329 0.6721 -0.1214 0.074 Uiso 1 1 calc R U . . .
C16 C -0.0165(4) 0.5710(4) -0.11303(18) 0.0840(12) Uani 1 1 d . . . . .
H16 H -0.0046 0.5171 -0.1513 0.101 Uiso 1 1 calc R U . . .
C17 C -0.1154(4) 0.5580(4) -0.0751(2) 0.0777(11) Uani 1 1 d . . . . .
H17 H -0.1709 0.4962 -0.0878 0.093 Uiso 1 1 calc R U . . .
C18 C -0.1327(3) 0.6357(4) -0.0186(2) 0.0764(10) Uani 1 1 d . . . . .
H18 H -0.1996 0.6266 0.0075 0.092 Uiso 1 1 calc R U . . .
C19 C -0.0511(3) 0.7275(3) -0.00031(18) 0.0624(8) Uani 1 1 d . . . . .
H19 H -0.0634 0.7803 0.0383 0.075 Uiso 1 1 calc R U . . .
C20 C 0.1791(2) 0.9623(2) 0.14425(12) 0.0327(5) Uani 1 1 d . . . . .
C21 C 0.2341(2) 0.8515(2) 0.17151(12) 0.0326(5) Uani 1 1 d . . . . .
C22 C 0.3995(3) 0.7309(3) 0.18933(15) 0.0531(7) Uani 1 1 d . . . . .
H22 H 0.4793 0.7181 0.1829 0.064 Uiso 1 1 calc R U . . .
C23 C 0.3416(3) 0.6408(3) 0.22840(16) 0.0587(8) Uani 1 1 d . . . . .
H23 H 0.3816 0.5707 0.2473 0.070 Uiso 1 1 calc R U . . .
C24 C 0.2255(3) 0.6574(3) 0.23823(15) 0.0549(8) Uani 1 1 d . . . . .
H24 H 0.1845 0.5978 0.2638 0.066 Uiso 1 1 calc R U . . .
C25 C 0.1663(2) 0.7650(2) 0.20983(13) 0.0398(6) Uani 1 1 d . . . . .
C26 C 0.0465(2) 0.7912(3) 0.21818(14) 0.0486(7) Uani 1 1 d . . . . .
H26 H 0.0006 0.7338 0.2421 0.058 Uiso 1 1 calc R U . . .
C27 C -0.0029(2) 0.8989(3) 0.19189(15) 0.0509(7) Uani 1 1 d . . . . .
H27 H -0.0820 0.9155 0.1987 0.061 Uiso 1 1 calc R U . . .
C28 C 0.0640(2) 0.9864(3) 0.15429(14) 0.0436(6) Uani 1 1 d . . . . .
H28 H 0.0292 1.0604 0.1364 0.052 Uiso 1 1 calc R U . . .
N1 N 0.25032(18) 1.04847(18) 0.10498(9) 0.0330(5) Uani 1 1 d . . . . .
N2 N 0.35090(18) 0.8324(2) 0.16075(11) 0.0414(5) Uani 1 1 d . . . . .
O1 O 0.28208(18) 1.16649(17) 0.20467(9) 0.0494(5) Uani 1 1 d . . . . .
O2 O 0.30722(18) 1.13139(19) -0.19944(9) 0.0457(5) Uani 1 1 d . . . . .
H1O H 0.291(3) 1.191(3) -0.2225(17) 0.065(11) Uiso 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.899(3) . ?
C1 C2 1.393(3) . ?
C1 C6 1.405(3) . ?
C1 C9 1.464(3) . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.407(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.442(3) . ?
C7 C8 1.353(3) . ?
C7 C10 1.511(3) . ?
C8 N1 1.413(3) . ?
C8 C12 1.427(4) . ?
C9 O1 1.233(3) . ?
C9 N1 1.371(3) . ?
C10 C11 1.514(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O2 1.415(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.194(4) . ?
C13 C14 1.433(4) . ?
C14 C15 1.376(4) . ?
C14 C19 1.380(4) . ?
C15 C16 1.384(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(5) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C28 1.355(4) . ?
C20 C21 1.411(3) . ?
C20 N1 1.444(3) . ?
C21 N2 1.367(3) . ?
C21 C25 1.415(3) . ?
C22 N2 1.308(3) . ?
C22 C23 1.388(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.352(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.411(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.406(4) . ?
C26 C27 1.350(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.409(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O2 H1O 0.78(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.6(2) . . ?
C2 C1 C9 118.2(2) . . ?
C6 C1 C9 121.1(2) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.1(2) . . ?
C2 C3 Br1 118.78(19) . . ?
C4 C3 Br1 120.1(2) . . ?
C5 C4 C3 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 117.6(2) . . ?
C1 C6 C7 119.7(2) . . ?
C5 C6 C7 122.8(2) . . ?
C8 C7 C6 118.5(2) . . ?
C8 C7 C10 120.5(2) . . ?
C6 C7 C10 120.9(2) . . ?
C7 C8 N1 121.6(2) . . ?
C7 C8 C12 124.3(2) . . ?
N1 C8 C12 114.1(2) . . ?
O1 C9 N1 120.2(2) . . ?
O1 C9 C1 124.3(2) . . ?
N1 C9 C1 115.48(19) . . ?
C7 C10 C11 110.4(2) . . ?
C7 C10 H10A 109.6 . . ?
C11 C10 H10A 109.6 . . ?
C7 C10 H10B 109.6 . . ?
C11 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
O2 C11 C10 108.9(2) . . ?
O2 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
O2 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C13 C12 C8 175.5(3) . . ?
C12 C13 C14 175.7(3) . . ?
C15 C14 C19 118.8(3) . . ?
C15 C14 C13 121.6(3) . . ?
C19 C14 C13 119.6(2) . . ?
C14 C15 C16 119.7(3) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.9(3) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 121.1(3) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C28 C20 C21 121.2(2) . . ?
C28 C20 N1 121.5(2) . . ?
C21 C20 N1 117.3(2) . . ?
N2 C21 C20 118.9(2) . . ?
N2 C21 C25 122.5(2) . . ?
C20 C21 C25 118.6(2) . . ?
N2 C22 C23 125.3(3) . . ?
N2 C22 H22 117.3 . . ?
C23 C22 H22 117.3 . . ?
C24 C23 C22 118.3(3) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 124.2(2) . . ?
C26 C25 C21 119.0(2) . . ?
C24 C25 C21 116.8(2) . . ?
C27 C26 C25 120.8(3) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C28 120.8(2) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C20 C28 C27 119.7(3) . . ?
C20 C28 H28 120.2 . . ?
C27 C28 H28 120.2 . . ?
C9 N1 C8 123.4(2) . . ?
C9 N1 C20 117.59(18) . . ?
C8 N1 C20 118.45(19) . . ?
C22 N2 C21 116.9(2) . . ?
C11 O2 H1O 109(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(4) . . . . ?
C9 C1 C2 C3 176.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 Br1 -177.38(18) . . . . ?
C2 C3 C4 C5 0.2(4) . . . . ?
Br1 C3 C4 C5 177.9(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 0.7(4) . . . . ?
C9 C1 C6 C5 -176.0(2) . . . . ?
C2 C1 C6 C7 -179.8(2) . . . . ?
C9 C1 C6 C7 3.4(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C5 C6 C7 -179.6(2) . . . . ?
C1 C6 C7 C8 -4.6(3) . . . . ?
C5 C6 C7 C8 174.8(2) . . . . ?
C1 C6 C7 C10 171.3(2) . . . . ?
C5 C6 C7 C10 -9.3(4) . . . . ?
C6 C7 C8 N1 1.6(3) . . . . ?
C10 C7 C8 N1 -174.3(2) . . . . ?
C6 C7 C8 C12 -179.9(2) . . . . ?
C10 C7 C8 C12 4.2(4) . . . . ?
C2 C1 C9 O1 1.9(4) . . . . ?
C6 C1 C9 O1 178.7(2) . . . . ?
C2 C1 C9 N1 -176.0(2) . . . . ?
C6 C1 C9 N1 0.8(3) . . . . ?
C8 C7 C10 C11 99.4(3) . . . . ?
C6 C7 C10 C11 -76.4(3) . . . . ?
C7 C10 C11 O2 -175.7(2) . . . . ?
C19 C14 C15 C16 0.0(5) . . . . ?
C13 C14 C15 C16 -179.9(3) . . . . ?
C14 C15 C16 C17 0.5(6) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C16 C17 C18 C19 0.5(6) . . . . ?
C17 C18 C19 C14 -0.1(6) . . . . ?
C15 C14 C19 C18 -0.2(5) . . . . ?
C13 C14 C19 C18 179.8(3) . . . . ?
C28 C20 C21 N2 -179.1(2) . . . . ?
N1 C20 C21 N2 1.2(3) . . . . ?
C28 C20 C21 C25 0.1(3) . . . . ?
N1 C20 C21 C25 -179.6(2) . . . . ?
N2 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -0.7(5) . . . . ?
C23 C24 C25 C26 -179.0(3) . . . . ?
C23 C24 C25 C21 0.1(4) . . . . ?
N2 C21 C25 C26 -179.6(2) . . . . ?
C20 C21 C25 C26 1.2(3) . . . . ?
N2 C21 C25 C24 1.2(4) . . . . ?
C20 C21 C25 C24 -178.0(2) . . . . ?
C24 C25 C26 C27 177.3(3) . . . . ?
C21 C25 C26 C27 -1.8(4) . . . . ?
C25 C26 C27 C28 1.2(4) . . . . ?
C21 C20 C28 C27 -0.7(4) . . . . ?
N1 C20 C28 C27 178.9(2) . . . . ?
C26 C27 C28 C20 0.1(4) . . . . ?
O1 C9 N1 C8 178.0(2) . . . . ?
C1 C9 N1 C8 -4.1(3) . . . . ?
O1 C9 N1 C20 -10.5(3) . . . . ?
C1 C9 N1 C20 167.4(2) . . . . ?
C7 C8 N1 C9 2.9(4) . . . . ?
C12 C8 N1 C9 -175.7(2) . . . . ?
C7 C8 N1 C20 -168.5(2) . . . . ?
C12 C8 N1 C20 12.9(3) . . . . ?
C28 C20 N1 C9 88.0(3) . . . . ?
C21 C20 N1 C9 -92.4(3) . . . . ?
C28 C20 N1 C8 -100.1(3) . . . . ?
C21 C20 N1 C8 79.6(3) . . . . ?
C23 C22 N2 C21 1.1(4) . . . . ?
C20 C21 N2 C22 177.4(2) . . . . ?
C25 C21 N2 C22 -1.8(4) . . . . ?

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.701
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_ch3_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2041962'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H22 F N O2'
_chemical_formula_weight         447.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   8.783(4)
_cell_length_b                   12.932(5)
_cell_length_c                   20.255(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2300.5(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    828
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      18.50

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8307
_diffrn_reflns_av_unetI/netI     0.1855
_diffrn_reflns_av_R_equivalents  0.1023
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         22.371
_diffrn_reflns_theta_full        22.371
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             2722
_reflns_number_gt                1074
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0730P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2722
_refine_ls_number_parameters     313
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1638
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1909
_refine_ls_wR_factor_gt          0.1538
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 1.2226(7) 0.4940(4) 0.8134(3) 0.0410(15) Uani 1 1 d . . . . .
C2 C 1.3052(7) 0.5110(4) 0.8713(3) 0.0493(16) Uani 1 1 d . . . . .
H2 H 1.2696 0.4862 0.9115 0.059 Uiso 1 1 calc R U . . .
C3 C 1.4391(8) 0.5649(5) 0.8679(3) 0.0559(18) Uani 1 1 d . . . . .
C4 C 1.4980(8) 0.6061(5) 0.8109(3) 0.066(2) Uani 1 1 d . . . . .
H4 H 1.5895 0.6422 0.8108 0.079 Uiso 1 1 calc R U . . .
C5 C 1.4160(8) 0.5917(5) 0.7543(3) 0.064(2) Uani 1 1 d . . . . .
H5 H 1.4514 0.6196 0.7148 0.077 Uiso 1 1 calc R U . . .
C6 C 1.2787(7) 0.5352(4) 0.7548(3) 0.0481(16) Uani 1 1 d . . . . .
C7 C 1.2033(8) 0.5189(5) 0.6921(3) 0.0549(18) Uani 1 1 d . . . . .
C8 C 1.0160(7) 0.4160(4) 0.7544(3) 0.0460(16) Uani 1 1 d . . . . .
C9 C 1.0835(7) 0.4347(4) 0.8130(3) 0.0424(15) Uani 1 1 d . . . . .
C10 C 1.0130(7) 0.4232(5) 0.6318(3) 0.0509(17) Uani 1 1 d . . . . .
C11 C 0.8886(7) 0.4793(5) 0.6064(3) 0.0496(17) Uani 1 1 d . . . . .
C12 C 0.8294(7) 0.5578(4) 0.6399(2) 0.0330(14) Uani 1 1 d . . . . .
H12 H 0.8698 0.5782 0.6803 0.040 Uiso 1 1 calc R U . . .
C13 C 0.7143(9) 0.6049(5) 0.6146(4) 0.075(2) Uani 1 1 d . . . . .
H13 H 0.6719 0.6591 0.6386 0.090 Uiso 1 1 calc R U . . .
C14 C 0.6483(9) 0.5807(6) 0.5537(4) 0.078(2) Uani 1 1 d . . . . .
H14 H 0.5651 0.6175 0.5377 0.094 Uiso 1 1 calc R U . . .
C15 C 0.7103(9) 0.5016(6) 0.5189(3) 0.070(2) Uani 1 1 d . . . . .
H15 H 0.6698 0.4843 0.4779 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8332(8) 0.4459(5) 0.5434(3) 0.0540(17) Uani 1 1 d . . . . .
C17 C 0.9045(9) 0.3629(5) 0.5097(3) 0.065(2) Uani 1 1 d . . . . .
H17 H 0.8681 0.3432 0.4684 0.078 Uiso 1 1 calc R U . . .
C18 C 1.0240(9) 0.3116(5) 0.5360(3) 0.070(2) Uani 1 1 d . . . . .
H18 H 1.0689 0.2568 0.5136 0.084 Uiso 1 1 calc R U . . .
C19 C 1.0796(8) 0.3433(5) 0.5987(3) 0.0610(19) Uani 1 1 d . . . . .
H19 H 1.1623 0.3092 0.6173 0.073 Uiso 1 1 calc R U . . .
C20 C 0.8757(9) 0.3586(5) 0.7489(3) 0.0492(17) Uani 1 1 d . . . . .
C21 C 0.7576(9) 0.3129(5) 0.7438(3) 0.0513(17) Uani 1 1 d . . . . .
C22 C 0.6090(8) 0.2616(5) 0.7355(3) 0.0535(18) Uani 1 1 d . . . . .
C23 C 0.5439(9) 0.2938(6) 0.6697(4) 0.096(3) Uani 1 1 d . . . . .
H23A H 0.6086 0.2691 0.6349 0.144 Uiso 1 1 calc R U . . .
H23B H 0.5380 0.3679 0.6677 0.144 Uiso 1 1 calc R U . . .
H23C H 0.4439 0.2650 0.6646 0.144 Uiso 1 1 calc R U . . .
C24 C 0.5060(8) 0.2879(5) 0.7930(4) 0.081(2) Uani 1 1 d . . . . .
H24A H 0.4086 0.2556 0.7868 0.121 Uiso 1 1 calc R U . . .
H24B H 0.4931 0.3615 0.7955 0.121 Uiso 1 1 calc R U . . .
H24C H 0.5509 0.2632 0.8332 0.121 Uiso 1 1 calc R U . . .
C25 C 1.0151(7) 0.3989(4) 0.8762(3) 0.0435(16) Uani 1 1 d . . . . .
C26 C 0.8774(8) 0.4394(5) 0.8982(3) 0.0573(18) Uani 1 1 d . . . . .
H26 H 0.8219 0.4833 0.8709 0.069 Uiso 1 1 calc R U . . .
C27 C 0.8223(8) 0.4148(5) 0.9603(3) 0.070(2) Uani 1 1 d . . . . .
H27 H 0.7306 0.4432 0.9745 0.084 Uiso 1 1 calc R U . . .
C28 C 0.8999(10) 0.3498(5) 1.0009(3) 0.074(2) Uani 1 1 d . . . . .
H28 H 0.8620 0.3338 1.0425 0.088 Uiso 1 1 calc R U . . .
C29 C 1.0362(9) 0.3079(5) 0.9795(3) 0.065(2) Uani 1 1 d . . . . .
H29 H 1.0912 0.2644 1.0072 0.079 Uiso 1 1 calc R U . . .
C30 C 1.0903(8) 0.3303(5) 0.9176(3) 0.0569(18) Uani 1 1 d . . . . .
H30 H 1.1794 0.2988 0.9030 0.068 Uiso 1 1 calc R U . . .
F1 F 1.5208(4) 0.5762(3) 0.92510(17) 0.0782(12) Uani 1 1 d . . . . .
N1 N 1.0779(6) 0.4532(4) 0.6950(2) 0.0498(13) Uani 1 1 d . . . . .
O1 O 1.2462(6) 0.5561(3) 0.6389(2) 0.0781(15) Uani 1 1 d . . . . .
O2 O 0.6297(5) 0.1515(3) 0.7312(2) 0.0650(13) Uani 1 1 d D . . . .
H1O H 0.622(8) 0.150(5) 0.7765(11) 0.08(2) Uiso 1 1 d D . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.390(7) . ?
C1 C2 1.397(7) . ?
C1 C9 1.443(8) . ?
C2 C3 1.369(8) . ?
C2 H2 0.9300 . ?
C3 F1 1.370(6) . ?
C3 C4 1.372(8) . ?
C4 C5 1.367(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.447(7) . ?
C7 O1 1.239(7) . ?
C7 N1 1.393(7) . ?
C8 C9 1.348(7) . ?
C8 N1 1.406(7) . ?
C8 C20 1.443(9) . ?
C9 C25 1.488(8) . ?
C10 C19 1.364(8) . ?
C10 C11 1.409(8) . ?
C10 N1 1.453(7) . ?
C11 C12 1.328(7) . ?
C11 C16 1.431(7) . ?
C12 C13 1.286(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(9) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(9) . ?
C15 H15 0.9300 . ?
C16 C17 1.418(9) . ?
C17 C18 1.351(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.420(8) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.198(8) . ?
C21 C22 1.473(9) . ?
C22 O2 1.438(7) . ?
C22 C23 1.509(8) . ?
C22 C24 1.514(9) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C30 1.388(7) . ?
C25 C26 1.390(8) . ?
C26 C27 1.385(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.359(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.383(9) . ?
C28 H28 0.9300 . ?
C29 C30 1.373(8) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
O2 H1O 0.92(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.2(6) . . ?
C6 C1 C9 120.0(5) . . ?
C2 C1 C9 121.8(5) . . ?
C3 C2 C1 119.0(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 F1 117.5(6) . . ?
C2 C3 C4 124.3(6) . . ?
F1 C3 C4 118.2(6) . . ?
C5 C4 C3 117.1(7) . . ?
C5 C4 H4 121.5 . . ?
C3 C4 H4 121.5 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 120.5(5) . . ?
C1 C6 C7 122.0(6) . . ?
C5 C6 C7 117.4(6) . . ?
O1 C7 N1 120.9(5) . . ?
O1 C7 C6 124.6(6) . . ?
N1 C7 C6 114.5(6) . . ?
C9 C8 N1 121.5(6) . . ?
C9 C8 C20 122.4(6) . . ?
N1 C8 C20 116.0(5) . . ?
C8 C9 C1 118.2(5) . . ?
C8 C9 C25 121.6(6) . . ?
C1 C9 C25 120.2(5) . . ?
C19 C10 C11 122.9(6) . . ?
C19 C10 N1 117.8(6) . . ?
C11 C10 N1 119.3(6) . . ?
C12 C11 C10 120.7(6) . . ?
C12 C11 C16 123.6(6) . . ?
C10 C11 C16 115.7(6) . . ?
C13 C12 C11 117.8(6) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 C14 124.8(7) . . ?
C12 C13 H13 117.6 . . ?
C14 C13 H13 117.6 . . ?
C15 C14 C13 117.4(7) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C16 121.1(7) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 124.2(6) . . ?
C15 C16 C11 115.2(6) . . ?
C17 C16 C11 120.5(6) . . ?
C18 C17 C16 121.6(6) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 118.6(7) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C10 C19 C18 120.7(6) . . ?
C10 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C8 178.6(7) . . ?
C20 C21 C22 176.8(7) . . ?
O2 C22 C21 109.9(5) . . ?
O2 C22 C23 105.6(5) . . ?
C21 C22 C23 108.2(6) . . ?
O2 C22 C24 110.1(5) . . ?
C21 C22 C24 109.9(5) . . ?
C23 C22 C24 113.1(6) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 117.5(6) . . ?
C30 C25 C9 121.7(6) . . ?
C26 C25 C9 120.6(5) . . ?
C27 C26 C25 120.5(6) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 121.1(7) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 119.1(7) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
C30 C29 C28 120.2(6) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C25 121.4(6) . . ?
C29 C30 H30 119.3 . . ?
C25 C30 H30 119.3 . . ?
C7 N1 C8 123.3(5) . . ?
C7 N1 C10 115.9(5) . . ?
C8 N1 C10 120.8(5) . . ?
C22 O2 H1O 87(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.7(8) . . . . ?
C9 C1 C2 C3 177.7(5) . . . . ?
C1 C2 C3 F1 -177.1(5) . . . . ?
C1 C2 C3 C4 1.5(10) . . . . ?
C2 C3 C4 C5 0.0(10) . . . . ?
F1 C3 C4 C5 178.5(5) . . . . ?
C3 C4 C5 C6 -1.1(10) . . . . ?
C2 C1 C6 C5 0.6(9) . . . . ?
C9 C1 C6 C5 -178.9(5) . . . . ?
C2 C1 C6 C7 178.1(5) . . . . ?
C9 C1 C6 C7 -1.3(8) . . . . ?
C4 C5 C6 C1 0.9(10) . . . . ?
C4 C5 C6 C7 -176.8(6) . . . . ?
C1 C6 C7 O1 178.0(6) . . . . ?
C5 C6 C7 O1 -4.4(9) . . . . ?
C1 C6 C7 N1 -4.4(8) . . . . ?
C5 C6 C7 N1 173.2(6) . . . . ?
N1 C8 C9 C1 -0.3(8) . . . . ?
C20 C8 C9 C1 -179.2(5) . . . . ?
N1 C8 C9 C25 177.6(5) . . . . ?
C20 C8 C9 C25 -1.3(8) . . . . ?
C6 C1 C9 C8 3.8(8) . . . . ?
C2 C1 C9 C8 -175.7(5) . . . . ?
C6 C1 C9 C25 -174.2(5) . . . . ?
C2 C1 C9 C25 6.4(8) . . . . ?
C19 C10 C11 C12 -178.7(6) . . . . ?
N1 C10 C11 C12 -0.9(8) . . . . ?
C19 C10 C11 C16 1.2(9) . . . . ?
N1 C10 C11 C16 179.0(5) . . . . ?
C10 C11 C12 C13 -178.8(6) . . . . ?
C16 C11 C12 C13 1.3(9) . . . . ?
C11 C12 C13 C14 -1.2(10) . . . . ?
C12 C13 C14 C15 0.1(11) . . . . ?
C13 C14 C15 C16 0.9(11) . . . . ?
C14 C15 C16 C17 -179.5(7) . . . . ?
C14 C15 C16 C11 -0.8(9) . . . . ?
C12 C11 C16 C15 -0.3(9) . . . . ?
C10 C11 C16 C15 179.8(5) . . . . ?
C12 C11 C16 C17 178.5(6) . . . . ?
C10 C11 C16 C17 -1.4(8) . . . . ?
C15 C16 C17 C18 179.9(6) . . . . ?
C11 C16 C17 C18 1.3(10) . . . . ?
C16 C17 C18 C19 -0.8(10) . . . . ?
C11 C10 C19 C18 -0.8(10) . . . . ?
N1 C10 C19 C18 -178.6(6) . . . . ?
C17 C18 C19 C10 0.5(10) . . . . ?
C8 C9 C25 C30 118.9(6) . . . . ?
C1 C9 C25 C30 -63.2(7) . . . . ?
C8 C9 C25 C26 -65.9(7) . . . . ?
C1 C9 C25 C26 112.0(6) . . . . ?
C30 C25 C26 C27 2.7(9) . . . . ?
C9 C25 C26 C27 -172.7(5) . . . . ?
C25 C26 C27 C28 -0.8(10) . . . . ?
C26 C27 C28 C29 0.0(11) . . . . ?
C27 C28 C29 C30 -1.2(10) . . . . ?
C28 C29 C30 C25 3.2(10) . . . . ?
C26 C25 C30 C29 -3.9(9) . . . . ?
C9 C25 C30 C29 171.5(6) . . . . ?
O1 C7 N1 C8 -174.3(6) . . . . ?
C6 C7 N1 C8 8.0(8) . . . . ?
O1 C7 N1 C10 6.3(8) . . . . ?
C6 C7 N1 C10 -171.4(5) . . . . ?
C9 C8 N1 C7 -6.0(8) . . . . ?
C20 C8 N1 C7 173.0(5) . . . . ?
C9 C8 N1 C10 173.5(5) . . . . ?
C20 C8 N1 C10 -7.6(8) . . . . ?
C19 C10 N1 C7 82.7(7) . . . . ?
C11 C10 N1 C7 -95.1(7) . . . . ?
C19 C10 N1 C8 -96.8(7) . . . . ?
C11 C10 N1 C8 85.4(7) . . . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_S2
_database_code_depnum_ccdc_archive 'CCDC 2041992'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-02 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H20 N2 O2'
_chemical_formula_sum            'C28 H20 N2 O2'
_chemical_formula_weight         416.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.0317(4)
_cell_length_b                   18.8318(12)
_cell_length_c                   8.3435(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.423(2)
_cell_angle_gamma                90
_cell_volume                     1089.93(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4230
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      24.14

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7041
_exptl_absorpt_correction_T_max  07455
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16022
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.163
_diffrn_reflns_theta_max         27.071
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4777
_reflns_number_gt                2644
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.938
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.038(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 977 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.4(8)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4777
_refine_ls_number_parameters     290
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1154
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1502
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.5116(6) 0.6521(3) 0.7574(6) 0.0636(13) Uani 1 1 d . . . . .
H1 H 0.4945 0.6367 0.8601 0.076 Uiso 1 1 calc R U . . .
C2 C 0.3681(7) 0.6943(3) 0.6635(8) 0.0740(15) Uani 1 1 d . . . . .
H2 H 0.2572 0.7065 0.7045 0.089 Uiso 1 1 calc R U . . .
C3 C 0.3920(6) 0.7170(3) 0.5144(7) 0.0626(14) Uani 1 1 d . . . . .
H3 H 0.2966 0.7443 0.4530 0.075 Uiso 1 1 calc R U . . .
C4 C 0.5593(6) 0.6998(2) 0.4515(5) 0.0474(11) Uani 1 1 d . . . . .
C5 C 0.5928(7) 0.7231(3) 0.2985(6) 0.0595(13) Uani 1 1 d . . . . .
H5 H 0.5017 0.7508 0.2333 0.071 Uiso 1 1 calc R U . . .
C6 C 0.7593(8) 0.7047(3) 0.2470(6) 0.0680(14) Uani 1 1 d . . . . .
H6 H 0.7843 0.7201 0.1466 0.082 Uiso 1 1 calc R U . . .
C7 C 0.8918(7) 0.6627(3) 0.3460(6) 0.0654(14) Uani 1 1 d . . . . .
H7 H 1.0045 0.6504 0.3078 0.079 Uiso 1 1 calc R U . . .
C8 C 0.7028(5) 0.6575(2) 0.5443(5) 0.0430(10) Uani 1 1 d . . . . .
C9 C 0.6724(6) 0.6339(2) 0.6993(5) 0.0460(11) Uani 1 1 d . . . . .
C10 C 0.9699(6) 0.6170(2) 0.8876(5) 0.0477(11) Uani 1 1 d . . . . .
C11 C 1.1152(5) 0.5681(2) 0.9661(5) 0.0467(11) Uani 1 1 d . . . . .
C12 C 1.2702(6) 0.5941(3) 1.0766(5) 0.0524(12) Uani 1 1 d . . . . .
H12 H 1.2759 0.6422 1.1017 0.063 Uiso 1 1 calc R U . . .
C13 C 1.4127(6) 0.5503(3) 1.1478(6) 0.0617(13) Uani 1 1 d . . . . .
H13 H 1.5143 0.5683 1.2222 0.074 Uiso 1 1 calc R U . . .
C14 C 1.4059(7) 0.4784(3) 1.1091(6) 0.0680(14) Uani 1 1 d . . . . .
H14 H 1.5045 0.4485 1.1563 0.082 Uiso 1 1 calc R U . . .
C15 C 1.2552(6) 0.4515(3) 1.0018(6) 0.0647(14) Uani 1 1 d . . . . .
H15 H 1.2532 0.4033 0.9769 0.078 Uiso 1 1 calc R U . . .
C16 C 1.1031(6) 0.4951(2) 0.9285(5) 0.0476(11) Uani 1 1 d . . . . .
C17 C 0.9377(6) 0.4676(2) 0.8233(5) 0.0495(11) Uani 1 1 d . . . . .
C18 C 0.7973(6) 0.5138(2) 0.7591(5) 0.0466(11) Uani 1 1 d . . . . .
C19 C 0.9130(7) 0.3892(2) 0.7874(6) 0.0570(12) Uani 1 1 d . . . . .
H19A H 0.8205 0.3827 0.6886 0.068 Uiso 1 1 calc R U . . .
H19B H 1.0351 0.3694 0.7695 0.068 Uiso 1 1 calc R U . . .
C20 C 0.8452(8) 0.3504(3) 0.9226(7) 0.0735(15) Uani 1 1 d . . . . .
H20A H 0.9381 0.3560 1.0215 0.088 Uiso 1 1 calc R U . . .
H20B H 0.7232 0.3699 0.9413 0.088 Uiso 1 1 calc R U . . .
C21 C 0.6222(7) 0.4913(2) 0.6606(6) 0.0521(12) Uani 1 1 d . . . . .
C22 C 0.4720(7) 0.4704(2) 0.5863(6) 0.0531(11) Uani 1 1 d . . . . .
C23 C 0.2937(6) 0.4442(2) 0.5017(5) 0.0513(12) Uani 1 1 d . . . . .
C24 C 0.2787(7) 0.3737(2) 0.4515(7) 0.0651(14) Uani 1 1 d . . . . .
H24 H 0.3864 0.3443 0.4700 0.078 Uiso 1 1 calc R U . . .
C25 C 0.1053(8) 0.3472(3) 0.3746(7) 0.0726(15) Uani 1 1 d . . . . .
H25 H 0.0964 0.3001 0.3404 0.087 Uiso 1 1 calc R U . . .
C26 C -0.0543(7) 0.3899(3) 0.3483(6) 0.0710(15) Uani 1 1 d . . . . .
H26 H -0.1722 0.3715 0.2992 0.085 Uiso 1 1 calc R U . . .
C27 C -0.0403(7) 0.4592(3) 0.3940(6) 0.0710(15) Uani 1 1 d . . . . .
H27 H -0.1484 0.4883 0.3728 0.085 Uiso 1 1 calc R U . . .
C28 C 0.1308(7) 0.4869(3) 0.4707(6) 0.0629(13) Uani 1 1 d . . . . .
H28 H 0.1378 0.5343 0.5022 0.075 Uiso 1 1 calc R U . . .
N1 N 0.8135(5) 0.58726(17) 0.7900(4) 0.0455(9) Uani 1 1 d . . . . .
N2 N 0.8693(5) 0.6388(2) 0.4907(5) 0.0549(10) Uani 1 1 d . . . . .
O1 O 0.9780(5) 0.68269(16) 0.9035(4) 0.0631(9) Uani 1 1 d . . . . .
O2 O 0.8225(6) 0.27703(17) 0.8833(5) 0.0922(13) Uani 1 1 d . . . . .
H2A H 0.8595 0.2531 0.9645 0.138 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
C1 C9 1.345(6) . ?
C1 C2 1.417(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.351(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(6) . ?
C4 C8 1.412(6) . ?
C5 C6 1.356(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.388(7) . ?
C6 H6 0.9300 . ?
C7 N2 1.323(6) . ?
C7 H7 0.9300 . ?
C8 N2 1.367(5) . ?
C8 C9 1.416(6) . ?
C9 N1 1.444(5) . ?
C10 O1 1.245(5) . ?
C10 N1 1.376(5) . ?
C10 C11 1.449(6) . ?
C11 C12 1.396(6) . ?
C11 C16 1.410(6) . ?
C12 C13 1.357(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.391(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.406(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.434(6) . ?
C17 C18 1.359(6) . ?
C17 C19 1.511(6) . ?
C18 N1 1.409(5) . ?
C18 C21 1.428(6) . ?
C19 C20 1.487(7) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 O2 1.422(6) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.201(6) . ?
C22 C23 1.422(6) . ?
C23 C28 1.389(6) . ?
C23 C24 1.392(6) . ?
C24 C25 1.376(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.369(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.358(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.370(7) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
O2 H2A 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 120.5(5) . . ?
C9 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C3 C2 C1 120.1(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.6(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 122.9(4) . . ?
C3 C4 C8 119.5(4) . . ?
C5 C4 C8 117.6(4) . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C5 C6 C7 119.1(5) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
N2 C7 C6 124.7(5) . . ?
N2 C7 H7 117.7 . . ?
C6 C7 H7 117.7 . . ?
N2 C8 C4 122.7(4) . . ?
N2 C8 C9 118.9(4) . . ?
C4 C8 C9 118.5(4) . . ?
C1 C9 C8 120.7(4) . . ?
C1 C9 N1 120.8(4) . . ?
C8 C9 N1 118.4(4) . . ?
O1 C10 N1 119.0(4) . . ?
O1 C10 C11 124.5(4) . . ?
N1 C10 C11 116.4(4) . . ?
C12 C11 C16 120.1(4) . . ?
C12 C11 C10 119.5(4) . . ?
C16 C11 C10 120.5(4) . . ?
C13 C12 C11 121.1(5) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.7(4) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 121.4(5) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C15 C16 C11 117.3(4) . . ?
C15 C16 C17 122.6(4) . . ?
C11 C16 C17 120.1(4) . . ?
C18 C17 C16 118.3(4) . . ?
C18 C17 C19 119.7(4) . . ?
C16 C17 C19 122.0(4) . . ?
C17 C18 N1 121.7(4) . . ?
C17 C18 C21 122.6(4) . . ?
N1 C18 C21 115.7(4) . . ?
C20 C19 C17 111.8(4) . . ?
C20 C19 H19A 109.3 . . ?
C17 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C17 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
O2 C20 C19 109.9(4) . . ?
O2 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
O2 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 C18 175.9(5) . . ?
C21 C22 C23 178.4(5) . . ?
C28 C23 C24 118.5(4) . . ?
C28 C23 C22 121.7(4) . . ?
C24 C23 C22 119.8(4) . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C27 C26 C25 120.0(5) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C26 C27 C28 121.0(5) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C27 C28 C23 120.1(5) . . ?
C27 C28 H28 120.0 . . ?
C23 C28 H28 120.0 . . ?
C10 N1 C18 122.7(3) . . ?
C10 N1 C9 118.5(3) . . ?
C18 N1 C9 118.3(3) . . ?
C7 N2 C8 116.6(4) . . ?
C20 O2 H2A 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 -0.2(8) . . . . ?
C1 C2 C3 C4 -0.7(8) . . . . ?
C2 C3 C4 C5 -178.9(5) . . . . ?
C2 C3 C4 C8 0.8(7) . . . . ?
C3 C4 C5 C6 179.4(4) . . . . ?
C8 C4 C5 C6 -0.4(6) . . . . ?
C4 C5 C6 C7 0.7(7) . . . . ?
C5 C6 C7 N2 -0.5(8) . . . . ?
C3 C4 C8 N2 -180.0(4) . . . . ?
C5 C4 C8 N2 -0.3(6) . . . . ?
C3 C4 C8 C9 -0.1(6) . . . . ?
C5 C4 C8 C9 179.6(4) . . . . ?
C2 C1 C9 C8 1.0(7) . . . . ?
C2 C1 C9 N1 -176.1(4) . . . . ?
N2 C8 C9 C1 179.1(4) . . . . ?
C4 C8 C9 C1 -0.8(6) . . . . ?
N2 C8 C9 N1 -3.8(6) . . . . ?
C4 C8 C9 N1 176.4(3) . . . . ?
O1 C10 C11 C12 4.7(6) . . . . ?
N1 C10 C11 C12 -175.1(4) . . . . ?
O1 C10 C11 C16 -173.8(4) . . . . ?
N1 C10 C11 C16 6.5(6) . . . . ?
C16 C11 C12 C13 0.9(6) . . . . ?
C10 C11 C12 C13 -177.5(4) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C15 -1.1(7) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C11 1.9(7) . . . . ?
C14 C15 C16 C17 -176.1(5) . . . . ?
C12 C11 C16 C15 -2.2(6) . . . . ?
C10 C11 C16 C15 176.2(4) . . . . ?
C12 C11 C16 C17 175.9(4) . . . . ?
C10 C11 C16 C17 -5.7(6) . . . . ?
C15 C16 C17 C18 179.5(4) . . . . ?
C11 C16 C17 C18 1.5(6) . . . . ?
C15 C16 C17 C19 1.6(7) . . . . ?
C11 C16 C17 C19 -176.4(4) . . . . ?
C16 C17 C18 N1 1.7(6) . . . . ?
C19 C17 C18 N1 179.6(4) . . . . ?
C16 C17 C18 C21 -176.4(4) . . . . ?
C19 C17 C18 C21 1.6(7) . . . . ?
C18 C17 C19 C20 -99.2(5) . . . . ?
C16 C17 C19 C20 78.7(6) . . . . ?
C17 C19 C20 O2 179.5(4) . . . . ?
C28 C23 C24 C25 -0.7(7) . . . . ?
C22 C23 C24 C25 177.8(5) . . . . ?
C23 C24 C25 C26 -0.6(8) . . . . ?
C24 C25 C26 C27 1.9(8) . . . . ?
C25 C26 C27 C28 -1.9(8) . . . . ?
C26 C27 C28 C23 0.6(8) . . . . ?
C24 C23 C28 C27 0.7(7) . . . . ?
C22 C23 C28 C27 -177.7(4) . . . . ?
O1 C10 N1 C18 176.9(4) . . . . ?
C11 C10 N1 C18 -3.4(5) . . . . ?
O1 C10 N1 C9 5.0(6) . . . . ?
C11 C10 N1 C9 -175.3(4) . . . . ?
C17 C18 N1 C10 -0.7(6) . . . . ?
C21 C18 N1 C10 177.5(4) . . . . ?
C17 C18 N1 C9 171.2(4) . . . . ?
C21 C18 N1 C9 -10.6(6) . . . . ?
C1 C9 N1 C10 -95.8(5) . . . . ?
C8 C9 N1 C10 87.0(5) . . . . ?
C1 C9 N1 C18 91.9(5) . . . . ?
C8 C9 N1 C18 -85.3(5) . . . . ?
C6 C7 N2 C8 -0.1(7) . . . . ?
C4 C8 N2 C7 0.5(6) . . . . ?
C9 C8 N2 C7 -179.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.82 1.97 2.734(4) 155.5 2_747

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_CH5
_database_code_depnum_ccdc_archive 'CCDC 2042374'
loop_
_audit_author_name
_audit_author_address
'Prasad Anaspure'
;Linnaeus University
Sweden
;
_audit_update_record             
;
2020-11-04 deposited with the CCDC.	2023-01-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 N2 O3'
_chemical_formula_sum            'C30 H24 N2 O3'
_chemical_formula_weight         460.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   12.6907(7)
_cell_length_b                   16.3431(9)
_cell_length_c                   13.3615(9)
_cell_angle_alpha                90
_cell_angle_beta                 118.292(2)
_cell_angle_gamma                90
_cell_volume                     2440.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6938
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      24.43

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6861
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27482
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.133
_diffrn_reflns_theta_max         25.233
_diffrn_reflns_theta_full        25.233
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4393
_reflns_number_gt                2922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.9077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4393
_refine_ls_number_parameters     323
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.0518(2) 0.58225(15) 0.5990(2) 0.0632(7) Uani 1 1 d . . . . .
H1 H 0.1026 0.5429 0.6486 0.076 Uiso 1 1 calc R U . . .
C2 C -0.0484(3) 0.60426(18) 0.6092(3) 0.0754(8) Uani 1 1 d . . . . .
H2 H -0.0635 0.5799 0.6640 0.090 Uiso 1 1 calc R U . . .
C3 C -0.1236(2) 0.66154(16) 0.5383(3) 0.0666(7) Uani 1 1 d . . . . .
H3 H -0.1908 0.6770 0.5445 0.080 Uiso 1 1 calc R U . . .
C4 C -0.10057(18) 0.69778(13) 0.4553(2) 0.0457(5) Uani 1 1 d . . . . .
C5 C -0.17406(19) 0.75741(14) 0.3775(2) 0.0574(7) Uani 1 1 d . . . . .
H5 H -0.2419 0.7757 0.3804 0.069 Uiso 1 1 calc R U . . .
C6 C -0.14688(19) 0.78845(14) 0.2983(2) 0.0589(7) Uani 1 1 d . . . . .
H6 H -0.1960 0.8278 0.2473 0.071 Uiso 1 1 calc R U . . .
C7 C -0.04473(18) 0.76112(12) 0.29335(19) 0.0458(5) Uani 1 1 d . . . . .
H7 H -0.0267 0.7823 0.2387 0.055 Uiso 1 1 calc R U . . .
C8 C 0.02785(15) 0.70416(11) 0.36754(17) 0.0342(5) Uani 1 1 d . . . . .
C9 C 0.00346(16) 0.67057(11) 0.45138(17) 0.0365(5) Uani 1 1 d . . . . .
C10 C 0.12080(16) 0.60372(11) 0.30127(16) 0.0335(5) Uani 1 1 d . . . . .
C11 C 0.22958(16) 0.57197(11) 0.30537(16) 0.0307(4) Uani 1 1 d . . . . .
C12 C 0.22424(17) 0.49972(11) 0.24697(17) 0.0369(5) Uani 1 1 d . . . . .
H12 H 0.1511 0.4733 0.2059 0.044 Uiso 1 1 calc R U . . .
C13 C 0.32426(18) 0.46733(11) 0.24917(18) 0.0412(5) Uani 1 1 d . . . . .
H13 H 0.3193 0.4192 0.2101 0.049 Uiso 1 1 calc R U . . .
C14 C 0.43475(17) 0.50689(12) 0.31065(17) 0.0388(5) Uani 1 1 d . . . . .
C15 C 0.44150(16) 0.57985(11) 0.36476(17) 0.0344(5) Uani 1 1 d . . . . .
H15 H 0.5143 0.6072 0.4021 0.041 Uiso 1 1 calc R U . . .
C16 C 0.33886(15) 0.61341(10) 0.36404(15) 0.0292(4) Uani 1 1 d . . . . .
C17 C 0.34264(15) 0.68931(10) 0.42123(16) 0.0304(4) Uani 1 1 d . . . . .
C18 C 0.24142(15) 0.71632(11) 0.42151(16) 0.0307(4) Uani 1 1 d . . . . .
C19 C 0.23793(15) 0.78669(12) 0.48363(17) 0.0353(5) Uani 1 1 d . . . . .
C20 C 0.22933(16) 0.84172(12) 0.53793(18) 0.0399(5) Uani 1 1 d . . . . .
C21 C 0.20702(17) 0.91094(12) 0.59768(18) 0.0419(5) Uani 1 1 d . . . . .
C22 C 0.0862(2) 0.89879(18) 0.5921(2) 0.0743(8) Uani 1 1 d . . . . .
H22A H 0.0857 0.8478 0.6274 0.111 Uiso 1 1 calc R U . . .
H22B H 0.0251 0.8981 0.5141 0.111 Uiso 1 1 calc R U . . .
H22C H 0.0712 0.9428 0.6313 0.111 Uiso 1 1 calc R U . . .
C23 C 0.2144(3) 0.98989(15) 0.5428(2) 0.0793(9) Uani 1 1 d . . . . .
H23A H 0.2020 1.0353 0.5816 0.119 Uiso 1 1 calc R U . . .
H23B H 0.1540 0.9903 0.4645 0.119 Uiso 1 1 calc R U . . .
H23C H 0.2920 0.9944 0.5472 0.119 Uiso 1 1 calc R U . . .
C24 C 0.45401(15) 0.73917(11) 0.47404(16) 0.0335(5) Uani 1 1 d . . . . .
C25 C 0.55505(17) 0.71388(13) 0.57010(18) 0.0438(5) Uani 1 1 d . . . . .
H25 H 0.5536 0.6653 0.6057 0.053 Uiso 1 1 calc R U . . .
C26 C 0.65885(18) 0.76042(16) 0.6139(2) 0.0542(6) Uani 1 1 d . . . . .
H26 H 0.7264 0.7429 0.6788 0.065 Uiso 1 1 calc R U . . .
C27 C 0.6626(2) 0.83176(15) 0.5624(2) 0.0591(7) Uani 1 1 d . . . . .
H27 H 0.7325 0.8625 0.5917 0.071 Uiso 1 1 calc R U . . .
C28 C 0.5635(2) 0.85735(16) 0.4683(3) 0.0751(8) Uani 1 1 d . . . . .
H28 H 0.5654 0.9059 0.4329 0.090 Uiso 1 1 calc R U . . .
C29 C 0.4600(2) 0.81181(14) 0.4249(2) 0.0613(7) Uani 1 1 d . . . . .
H29 H 0.3925 0.8306 0.3609 0.074 Uiso 1 1 calc R U . . .
C30 C 0.64677(19) 0.50042(16) 0.3820(2) 0.0637(7) Uani 1 1 d . . . . .
H30A H 0.6557 0.5515 0.3513 0.095 Uiso 1 1 calc R U . . .
H30B H 0.7058 0.4624 0.3850 0.095 Uiso 1 1 calc R U . . .
H30C H 0.6573 0.5091 0.4573 0.095 Uiso 1 1 calc R U . . .
N1 N 0.07954(15) 0.61320(10) 0.52405(15) 0.0462(5) Uani 1 1 d . . . . .
N2 N 0.13244(12) 0.67493(9) 0.36144(13) 0.0324(4) Uani 1 1 d . . . . .
O1 O 0.52961(13) 0.46809(9) 0.31108(14) 0.0571(4) Uani 1 1 d . . . . .
O2 O 0.02238(11) 0.57003(9) 0.24847(13) 0.0476(4) Uani 1 1 d . . . . .
O3 O 0.29032(14) 0.91170(9) 0.71495(13) 0.0518(4) Uani 1 1 d . . . . .
H3A H 0.367(2) 0.9145(15) 0.720(2) 0.077(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.310(3) . ?
C1 C2 1.389(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.408(3) . ?
C4 C9 1.418(3) . ?
C5 C6 1.358(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.402(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.354(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.407(3) . ?
C8 N2 1.449(2) . ?
C9 N1 1.366(3) . ?
C10 O2 1.235(2) . ?
C10 N2 1.382(2) . ?
C10 C11 1.451(2) . ?
C11 C12 1.399(3) . ?
C11 C16 1.402(2) . ?
C12 C13 1.363(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.403(3) . ?
C13 H13 0.9300 . ?
C14 O1 1.358(2) . ?
C14 C15 1.376(3) . ?
C15 C16 1.409(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.446(2) . ?
C17 C18 1.360(2) . ?
C17 C24 1.488(2) . ?
C18 N2 1.401(2) . ?
C18 C19 1.431(3) . ?
C19 C20 1.193(3) . ?
C20 C21 1.487(3) . ?
C21 O3 1.415(2) . ?
C21 C23 1.509(3) . ?
C21 C22 1.512(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C29 1.376(3) . ?
C24 C25 1.379(3) . ?
C25 C26 1.388(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.366(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.357(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.375(3) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 O1 1.433(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
O3 H3A 0.94(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.4(2) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 124.2(2) . . ?
C3 C4 C9 116.3(2) . . ?
C5 C4 C9 119.5(2) . . ?
C6 C5 C4 120.7(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.41(18) . . ?
C7 C8 N2 120.61(18) . . ?
C9 C8 N2 117.97(16) . . ?
N1 C9 C8 119.06(17) . . ?
N1 C9 C4 123.08(19) . . ?
C8 C9 C4 117.87(18) . . ?
O2 C10 N2 120.53(16) . . ?
O2 C10 C11 123.26(17) . . ?
N2 C10 C11 116.21(16) . . ?
C12 C11 C16 119.54(16) . . ?
C12 C11 C10 119.14(16) . . ?
C16 C11 C10 121.30(16) . . ?
C13 C12 C11 121.16(18) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 119.75(18) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
O1 C14 C15 124.62(18) . . ?
O1 C14 C13 115.17(17) . . ?
C15 C14 C13 120.21(17) . . ?
C14 C15 C16 120.43(17) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 118.82(16) . . ?
C11 C16 C17 119.09(16) . . ?
C15 C16 C17 122.09(16) . . ?
C18 C17 C16 119.03(16) . . ?
C18 C17 C24 120.47(16) . . ?
C16 C17 C24 120.44(15) . . ?
C17 C18 N2 121.27(16) . . ?
C17 C18 C19 123.46(16) . . ?
N2 C18 C19 115.26(15) . . ?
C20 C19 C18 174.7(2) . . ?
C19 C20 C21 174.8(2) . . ?
O3 C21 C20 111.63(16) . . ?
O3 C21 C23 110.17(19) . . ?
C20 C21 C23 108.53(19) . . ?
O3 C21 C22 105.27(19) . . ?
C20 C21 C22 108.68(17) . . ?
C23 C21 C22 112.6(2) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 117.71(18) . . ?
C29 C24 C17 120.09(17) . . ?
C25 C24 C17 122.17(18) . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 120.5(2) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C28 C27 C26 119.5(2) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C27 C28 C29 120.3(2) . . ?
C27 C28 H28 119.9 . . ?
C29 C28 H28 119.9 . . ?
C28 C29 C24 121.6(2) . . ?
C28 C29 H29 119.2 . . ?
C24 C29 H29 119.2 . . ?
O1 C30 H30A 109.5 . . ?
O1 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O1 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C1 N1 C9 116.92(19) . . ?
C10 N2 C18 122.97(15) . . ?
C10 N2 C8 117.53(15) . . ?
C18 N2 C8 119.38(15) . . ?
C14 O1 C30 118.06(16) . . ?
C21 O3 H3A 106.7(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.2(4) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C5 179.6(2) . . . . ?
C2 C3 C4 C9 0.2(4) . . . . ?
C3 C4 C5 C6 -178.8(2) . . . . ?
C9 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C8 -0.4(4) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C6 C7 C8 N2 179.04(19) . . . . ?
C7 C8 C9 N1 179.92(18) . . . . ?
N2 C8 C9 N1 1.0(3) . . . . ?
C7 C8 C9 C4 0.5(3) . . . . ?
N2 C8 C9 C4 -178.45(17) . . . . ?
C3 C4 C9 N1 -0.8(3) . . . . ?
C5 C4 C9 N1 179.76(19) . . . . ?
C3 C4 C9 C8 178.55(19) . . . . ?
C5 C4 C9 C8 -0.9(3) . . . . ?
O2 C10 C11 C12 0.1(3) . . . . ?
N2 C10 C11 C12 179.54(17) . . . . ?
O2 C10 C11 C16 178.35(18) . . . . ?
N2 C10 C11 C16 -2.2(3) . . . . ?
C16 C11 C12 C13 2.2(3) . . . . ?
C10 C11 C12 C13 -179.49(18) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 O1 177.57(19) . . . . ?
C12 C13 C14 C15 -2.6(3) . . . . ?
O1 C14 C15 C16 -176.90(18) . . . . ?
C13 C14 C15 C16 3.3(3) . . . . ?
C12 C11 C16 C15 -1.5(3) . . . . ?
C10 C11 C16 C15 -179.76(17) . . . . ?
C12 C11 C16 C17 178.15(17) . . . . ?
C10 C11 C16 C17 -0.1(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C14 C15 C16 C17 179.12(18) . . . . ?
C11 C16 C17 C18 3.3(3) . . . . ?
C15 C16 C17 C18 -177.03(17) . . . . ?
C11 C16 C17 C24 -173.66(17) . . . . ?
C15 C16 C17 C24 6.0(3) . . . . ?
C16 C17 C18 N2 -4.2(3) . . . . ?
C24 C17 C18 N2 172.80(16) . . . . ?
C16 C17 C18 C19 174.44(18) . . . . ?
C24 C17 C18 C19 -8.6(3) . . . . ?
C18 C17 C24 C29 -69.0(3) . . . . ?
C16 C17 C24 C29 107.9(2) . . . . ?
C18 C17 C24 C25 113.2(2) . . . . ?
C16 C17 C24 C25 -69.8(3) . . . . ?
C29 C24 C25 C26 -0.7(3) . . . . ?
C17 C24 C25 C26 177.16(18) . . . . ?
C24 C25 C26 C27 -0.2(3) . . . . ?
C25 C26 C27 C28 0.5(4) . . . . ?
C26 C27 C28 C29 0.0(4) . . . . ?
C27 C28 C29 C24 -0.8(4) . . . . ?
C25 C24 C29 C28 1.2(4) . . . . ?
C17 C24 C29 C28 -176.7(2) . . . . ?
C2 C1 N1 C9 -0.4(4) . . . . ?
C8 C9 N1 C1 -178.4(2) . . . . ?
C4 C9 N1 C1 0.9(3) . . . . ?
O2 C10 N2 C18 -179.10(17) . . . . ?
C11 C10 N2 C18 1.4(3) . . . . ?
O2 C10 N2 C8 4.9(3) . . . . ?
C11 C10 N2 C8 -174.56(16) . . . . ?
C17 C18 N2 C10 1.8(3) . . . . ?
C19 C18 N2 C10 -176.93(17) . . . . ?
C17 C18 N2 C8 177.73(17) . . . . ?
C19 C18 N2 C8 -1.0(2) . . . . ?
C7 C8 N2 C10 -95.2(2) . . . . ?
C9 C8 N2 C10 83.7(2) . . . . ?
C7 C8 N2 C18 88.6(2) . . . . ?
C9 C8 N2 C18 -92.4(2) . . . . ?
C15 C14 O1 C30 6.8(3) . . . . ?
C13 C14 O1 C30 -173.46(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.93 2.66 3.353(3) 132.0 3_566
C30 H30B N1 0.96 2.70 3.599(3) 156.4 3_666
O3 H3A O2 0.94(3) 1.85(3) 2.777(2) 172(2) 4_676

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.038

