# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2025

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

data_KB929_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2404673'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;Senior Principal Scientist
India
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 O3'
_chemical_formula_sum            'C22 H20 O3'
_chemical_formula_weight         332.38

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

_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                   7.4256(12)
_cell_length_b                   28.847(5)
_cell_length_c                   8.6123(14)
_cell_angle_alpha                90
_cell_angle_beta                 105.576(7)
_cell_angle_gamma                90
_cell_volume                     1777.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    9840
_cell_measurement_theta_min      2.8245
_cell_measurement_theta_max      30.131

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6875
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20484
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.848
_diffrn_reflns_theta_max         30.525
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.928
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.928
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5048
_reflns_number_gt                3641
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0699P)²+0.1707P] 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_number_reflns         5048
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1449
_refine_ls_wR_factor_gt          0.1307
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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
C1 C 0.58504(16) 0.65298(4) 0.33657(14) 0.0409(2) Uani 1 1 d . . . . .
C2 C 0.45903(17) 0.64642(4) 0.43814(15) 0.0460(3) Uani 1 1 d . . . . .
H2 H 0.441491 0.618248 0.484520 0.055 Uiso 1 1 calc R U . . .
C3 C 0.37127(17) 0.68571(4) 0.45699(15) 0.0446(3) Uani 1 1 d . . . . .
C4 C 0.4361(2) 0.72551(4) 0.37544(18) 0.0525(3) Uani 1 1 d . . . . .
H4A H 0.495735 0.748978 0.452911 0.063 Uiso 1 1 calc R U . . .
H4B H 0.332696 0.739466 0.295646 0.063 Uiso 1 1 calc R U . . .
C5 C 0.57462(17) 0.70374(4) 0.29662(15) 0.0426(3) Uani 1 1 d . . . . .
C6 C 0.22265(19) 0.68771(5) 0.54049(16) 0.0521(3) Uani 1 1 d . . . . .
C7 C -0.0138(2) 0.73409(6) 0.5972(2) 0.0662(4) Uani 1 1 d . . . . .
H7A H -0.074690 0.763264 0.565192 0.099 Uiso 1 1 calc R U . . .
H7B H 0.033448 0.733205 0.712421 0.099 Uiso 1 1 calc R U . . .
H7C H -0.101770 0.709344 0.562227 0.099 Uiso 1 1 calc R U . . .
C8 C 0.69092(16) 0.62029(4) 0.28837(14) 0.0403(2) Uani 1 1 d . . . . .
C9 C 0.78458(17) 0.62942(4) 0.15925(15) 0.0426(3) Uani 1 1 d . . . . .
C10 C 0.6859(2) 0.64587(5) 0.00924(16) 0.0530(3) Uani 1 1 d . . . . .
H10 H 0.558941 0.652257 -0.011140 0.064 Uiso 1 1 calc R U . . .
C11 C 0.7761(3) 0.65281(6) -0.11033(18) 0.0670(4) Uani 1 1 d . . . . .
H11 H 0.709332 0.663865 -0.210726 0.080 Uiso 1 1 calc R U . . .
C12 C 0.9644(3) 0.64340(6) -0.0813(2) 0.0711(5) Uani 1 1 d . . . . .
H12 H 1.024412 0.648240 -0.161859 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0624(2) 0.62702(6) 0.0655(2) 0.0667(4) Uani 1 1 d . . . . .
H13 H 1.189421 0.620757 0.084985 0.080 Uiso 1 1 calc R U . . .
C14 C 0.97357(19) 0.61963(5) 0.18595(18) 0.0530(3) Uani 1 1 d . . . . .
H14 H 1.041060 0.608043 0.285312 0.064 Uiso 1 1 calc R U . . .
C15 C 0.71357(16) 0.57299(4) 0.35766(15) 0.0436(3) Uani 1 1 d . . . . .
C16 C 0.70086(19) 0.53489(4) 0.25570(18) 0.0507(3) Uani 1 1 d . . . . .
H16 H 0.680976 0.539700 0.145606 0.061 Uiso 1 1 calc R U . . .
C17 C 0.71727(19) 0.48992(5) 0.3152(2) 0.0571(3) Uani 1 1 d . . . . .
C18 C 0.75168(19) 0.48372(5) 0.4799(2) 0.0592(4) Uani 1 1 d . . . . .
H18 H 0.764049 0.453717 0.520886 0.071 Uiso 1 1 calc R U . . .
C19 C 0.76838(18) 0.52062(5) 0.58590(18) 0.0543(3) Uani 1 1 d . . . . .
C20 C 0.74887(18) 0.56534(5) 0.52272(16) 0.0494(3) Uani 1 1 d . . . . .
H20 H 0.759607 0.590535 0.591989 0.059 Uiso 1 1 calc R U . . .
C21 C 0.6973(3) 0.44919(6) 0.2028(3) 0.0861(6) Uani 1 1 d . . . . .
H21A H 0.713320 0.459351 0.101185 0.129 Uiso 1 1 calc R U . . .
H21B H 0.575211 0.435835 0.186569 0.129 Uiso 1 1 calc R U . . .
H21C H 0.790533 0.426404 0.248843 0.129 Uiso 1 1 calc R U . . .
C22 C 0.8063(3) 0.51238(7) 0.7638(2) 0.0758(5) Uani 1 1 d . . . . .
H22A H 0.709342 0.493260 0.784224 0.114 Uiso 1 1 calc R U . . .
H22B H 0.809196 0.541527 0.818263 0.114 Uiso 1 1 calc R U . . .
H22C H 0.924706 0.497090 0.802854 0.114 Uiso 1 1 calc R U . . .
O2 O 0.13998(13) 0.72875(3) 0.52418(12) 0.0569(3) Uani 1 1 d . . . . .
O3 O 0.66379(15) 0.72511(3) 0.22228(13) 0.0597(3) Uani 1 1 d . . . . .
O1 O 0.158(2) 0.6537(3) 0.594(2) 0.0726(18) Uani 0.61(5) 1 d . . P A 1
O1D O 0.216(4) 0.6616(8) 0.645(3) 0.075(4) Uani 0.39(5) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.3619(16) . ?
C1 C2 1.4546(16) . ?
C1 C5 1.5015(16) . ?
C2 C3 1.3388(17) . ?
C2 H2 0.9300 . ?
C3 C6 1.4713(17) . ?
C3 C4 1.4915(17) . ?
C4 C5 1.5125(17) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O3 1.2066(14) . ?
C6 O1D 1.186(10) . ?
C6 O1 1.237(7) . ?
C6 O2 1.3235(16) . ?
C7 O2 1.4520(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C15 1.4807(16) . ?
C8 C9 1.4849(16) . ?
C9 C10 1.3866(18) . ?
C9 C14 1.3888(18) . ?
C10 C11 1.385(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.3874(19) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.3921(18) . ?
C15 C16 1.3940(18) . ?
C16 C17 1.3880(18) . ?
C16 H16 0.9300 . ?
C17 C18 1.383(2) . ?
C17 C21 1.504(2) . ?
C18 C19 1.386(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.3924(18) . ?
C19 C22 1.501(2) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
C8 C1 C2 127.63(11) . . ?
C8 C1 C5 127.14(10) . . ?
C2 C1 C5 105.23(10) . . ?
C3 C2 C1 112.06(11) . . ?
C3 C2 H2 124.0 . . ?
C1 C2 H2 124.0 . . ?
C2 C3 C6 123.09(12) . . ?
C2 C3 C4 111.42(11) . . ?
C6 C3 C4 125.40(11) . . ?
C3 C4 C5 103.67(10) . . ?
C3 C4 H4A 111.0 . . ?
C5 C4 H4A 111.0 . . ?
C3 C4 H4B 111.0 . . ?
C5 C4 H4B 111.0 . . ?
H4A C4 H4B 109.0 . . ?
O3 C5 C1 128.16(11) . . ?
O3 C5 C4 124.21(11) . . ?
C1 C5 C4 107.54(10) . . ?
O1D C6 O2 122.3(6) . . ?
O1 C6 O2 122.3(4) . . ?
O1D C6 C3 122.5(6) . . ?
O1 C6 C3 124.7(3) . . ?
O2 C6 C3 111.76(11) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 C8 C15 121.84(10) . . ?
C1 C8 C9 122.03(10) . . ?
C15 C8 C9 116.10(10) . . ?
C10 C9 C14 118.78(12) . . ?
C10 C9 C8 121.46(11) . . ?
C14 C9 C8 119.71(11) . . ?
C11 C10 C9 120.14(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.37(15) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C13 C12 C11 119.93(14) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.28(15) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.49(14) . . ?
C13 C14 H14 119.8 . . ?
C9 C14 H14 119.8 . . ?
C20 C15 C16 118.72(11) . . ?
C20 C15 C8 121.84(11) . . ?
C16 C15 C8 119.44(11) . . ?
C17 C16 C15 121.32(14) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 118.23(13) . . ?
C18 C17 C21 121.20(14) . . ?
C16 C17 C21 120.57(16) . . ?
C17 C18 C19 122.36(13) . . ?
C17 C18 H18 118.8 . . ?
C19 C18 H18 118.8 . . ?
C18 C19 C20 118.19(13) . . ?
C18 C19 C22 120.68(14) . . ?
C20 C19 C22 121.13(15) . . ?
C15 C20 C19 121.14(13) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C6 O2 C7 116.44(11) . . ?

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
C8 C1 C2 C3 -177.67(12) . . . . ?
C5 C1 C2 C3 2.66(15) . . . . ?
C1 C2 C3 C6 173.72(12) . . . . ?
C1 C2 C3 C4 -3.10(17) . . . . ?
C2 C3 C4 C5 2.15(16) . . . . ?
C6 C3 C4 C5 -174.59(12) . . . . ?
C8 C1 C5 O3 -4.1(2) . . . . ?
C2 C1 C5 O3 175.62(14) . . . . ?
C8 C1 C5 C4 179.13(13) . . . . ?
C2 C1 C5 C4 -1.19(13) . . . . ?
C3 C4 C5 O3 -177.42(13) . . . . ?
C3 C4 C5 C1 -0.45(14) . . . . ?
C2 C3 C6 O1D 29(2) . . . . ?
C4 C3 C6 O1D -154(2) . . . . ?
C2 C3 C6 O1 -3.7(13) . . . . ?
C4 C3 C6 O1 172.7(12) . . . . ?
C2 C3 C6 O2 -171.20(13) . . . . ?
C4 C3 C6 O2 5.2(2) . . . . ?
C2 C1 C8 C15 -10.1(2) . . . . ?
C5 C1 C8 C15 169.51(12) . . . . ?
C2 C1 C8 C9 167.63(12) . . . . ?
C5 C1 C8 C9 -12.77(19) . . . . ?
C1 C8 C9 C10 -53.17(17) . . . . ?
C15 C8 C9 C10 124.67(13) . . . . ?
C1 C8 C9 C14 129.44(13) . . . . ?
C15 C8 C9 C14 -52.72(16) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C8 C9 C10 C11 -178.16(13) . . . . ?
C9 C10 C11 C12 0.0(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C9 -0.9(2) . . . . ?
C10 C9 C14 C13 1.2(2) . . . . ?
C8 C9 C14 C13 178.62(13) . . . . ?
C1 C8 C15 C20 -44.59(17) . . . . ?
C9 C8 C15 C20 137.57(12) . . . . ?
C1 C8 C15 C16 135.93(13) . . . . ?
C9 C8 C15 C16 -41.92(16) . . . . ?
C20 C15 C16 C17 1.9(2) . . . . ?
C8 C15 C16 C17 -178.62(12) . . . . ?
C15 C16 C17 C18 -1.7(2) . . . . ?
C15 C16 C17 C21 178.11(14) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C21 C17 C18 C19 -179.18(15) . . . . ?
C17 C18 C19 C20 0.2(2) . . . . ?
C17 C18 C19 C22 -179.82(14) . . . . ?
C16 C15 C20 C19 -1.02(19) . . . . ?
C8 C15 C20 C19 179.49(11) . . . . ?
C18 C19 C20 C15 -0.01(19) . . . . ?
C22 C19 C20 C15 -179.96(13) . . . . ?
O1D C6 O2 C7 -22(2) . . . . ?
O1 C6 O2 C7 10.0(12) . . . . ?
C3 C6 O2 C7 177.88(12) . . . . ?

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.031



####################################################################### 
# 
# 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_KB1650_0m
_database_code_depnum_ccdc_archive 'CCDC 2404675'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;Senior Principal Scientist
India
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_weight         308.36

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'
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                   13.7298(16)
_cell_length_b                   8.6498(10)
_cell_length_c                   14.4582(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.461(3)
_cell_angle_gamma                90
_cell_volume                     1702.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6931
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26306
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.750
_diffrn_reflns_theta_max         28.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4229
_reflns_number_gt                2256
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0646P)²+0.2429P] 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_number_reflns         4229
_refine_ls_number_parameters     237
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0461
_refine_ls_wR_factor_ref         0.1541
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.003
_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 0.59518(14) 0.4894(2) 0.92397(13) 0.0777(5) Uani 1 1 d . . . . .
H1 H 0.542439 0.427863 0.899715 0.093 Uiso 1 1 calc R U . . .
C2 C 0.64810(19) 0.4504(3) 1.00832(16) 0.0979(7) Uani 1 1 d . . . . .
H2 H 0.631206 0.362834 1.039999 0.118 Uiso 1 1 calc R U . . .
C3 C 0.7252(2) 0.5398(3) 1.04543(14) 0.0997(8) Uani 1 1 d . . . . .
H3 H 0.760264 0.514558 1.102826 0.120 Uiso 1 1 calc R U . . .
C4 C 0.75055(15) 0.6673(3) 0.99756(14) 0.0892(6) Uani 1 1 d . . . . .
H4 H 0.803392 0.728155 1.022443 0.107 Uiso 1 1 calc R U . . .
C5 C 0.69792(13) 0.7062(2) 0.91220(12) 0.0718(5) Uani 1 1 d . . . . .
H5 H 0.716178 0.792435 0.880085 0.086 Uiso 1 1 calc R U . . .
C6 C 0.61876(11) 0.61813(19) 0.87453(11) 0.0589(4) Uani 1 1 d . . . . .
C7 C 0.55391(11) 0.65990(18) 0.78500(10) 0.0554(4) Uani 1 1 d . . . . .
H7 H 0.521604 0.563995 0.761597 0.066 Uiso 1 1 calc R U . . .
C8 C 0.47244(11) 0.7693(2) 0.80556(11) 0.0593(4) Uani 1 1 d . . . . .
C9 C 0.49180(15) 0.9020(2) 0.85769(13) 0.0803(5) Uani 1 1 d . . . . .
H9 H 0.556469 0.928567 0.878965 0.096 Uiso 1 1 calc R U . . .
C10 C 0.4161(2) 0.9960(3) 0.87867(16) 0.1013(7) Uani 1 1 d D . . . .
H10 H 0.430387 1.087668 0.911222 0.122 Uiso 1 1 calc R U . A 1
C12 C 0.30054(16) 0.8299(4) 0.79529(17) 0.1012(8) Uani 1 1 d D . . . .
H12 H 0.235980 0.808023 0.770873 0.121 Uiso 1 1 calc R U . B 1
C13 C 0.37574(12) 0.7356(2) 0.77405(13) 0.0763(5) Uani 1 1 d . . . . .
H13 H 0.360835 0.647822 0.737836 0.092 Uiso 1 1 calc R U . . .
C14 C 0.60796(10) 0.72224(17) 0.70635(10) 0.0525(4) Uani 1 1 d . . . . .
H14 H 0.640517 0.818936 0.727913 0.063 Uiso 1 1 calc R U . . .
C15 C 0.54212(11) 0.75544(17) 0.61467(10) 0.0538(4) Uani 1 1 d . . . . .
H15A H 0.509523 0.854539 0.617290 0.065 Uiso 1 1 calc R U . . .
H15B H 0.492746 0.675475 0.601472 0.065 Uiso 1 1 calc R U . . .
C16 C 0.61265(12) 0.75692(19) 0.54019(11) 0.0621(4) Uani 1 1 d . . . . .
H16 H 0.644176 0.858544 0.539979 0.075 Uiso 1 1 calc R U . . .
C17 C 0.68966(15) 0.6362(3) 0.57362(13) 0.0904(6) Uani 1 1 d . . . . .
H17A H 0.675660 0.539499 0.540587 0.109 Uiso 1 1 calc R U . . .
H17B H 0.754484 0.671236 0.563257 0.109 Uiso 1 1 calc R U . . .
C18 C 0.68455(11) 0.61549(19) 0.67601(11) 0.0611(4) Uani 1 1 d . . . . .
C19 C 0.56098(13) 0.7232(2) 0.44457(12) 0.0627(4) Uani 1 1 d . . . . .
C20 C 0.44692(19) 0.8135(3) 0.32112(15) 0.1071(8) Uani 1 1 d . . . . .
H20A H 0.493637 0.815318 0.277151 0.161 Uiso 1 1 calc R U . C 1
H20B H 0.400182 0.895436 0.307052 0.161 Uiso 1 1 calc R U . C 1
H20C H 0.413297 0.715948 0.317244 0.161 Uiso 1 1 calc R U . C 1
O1 O 0.73285(10) 0.52201(16) 0.72347(9) 0.0883(4) Uani 1 1 d . . . . .
C11 C 0.3206(6) 0.9549(10) 0.8519(8) 0.100(2) Uani 0.75(2) 1 d D U P D 1
H11 H 0.269807 1.011635 0.872028 0.121 Uiso 0.75(2) 1 calc R U P D 1
O2 O 0.4979(7) 0.8344(13) 0.4149(8) 0.0811(18) Uani 0.75(2) 1 d . U P D 1
O3 O 0.5771(5) 0.6124(9) 0.3988(5) 0.0950(14) Uani 0.75(2) 1 d . U P D 1
C11D C 0.3230(17) 0.972(3) 0.835(3) 0.112(8) Uani 0.25(2) 1 d D U P D 2
H11D H 0.276098 1.050447 0.831373 0.134 Uiso 0.25(2) 1 calc R U P D 2
O2D O 0.525(2) 0.838(3) 0.401(2) 0.085(6) Uani 0.25(2) 1 d . U P D 2
O3D O 0.541(3) 0.5976(16) 0.4115(15) 0.100(6) Uani 0.25(2) 1 d . U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.378(3) . ?
C1 C6 1.384(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(2) . ?
C7 C8 1.524(2) . ?
C7 C14 1.534(2) . ?
C7 H7 0.9800 . ?
C8 C13 1.378(2) . ?
C8 C9 1.380(3) . ?
C9 C10 1.384(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(7) . ?
C10 C11D 1.368(18) . ?
C10 H10 0.9300 . ?
C12 C11 1.362(8) . ?
C12 C11D 1.375(19) . ?
C12 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C18 1.507(2) . ?
C14 C15 1.531(2) . ?
C14 H14 0.9800 . ?
C15 C16 1.539(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C19 1.498(2) . ?
C16 C17 1.520(2) . ?
C16 H16 0.9800 . ?
C17 C18 1.502(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O1 1.2026(18) . ?
C19 O3 1.201(6) . ?
C19 O3D 1.204(15) . ?
C19 O2D 1.24(3) . ?
C19 O2 1.328(10) . ?
C20 O2 1.454(11) . ?
C20 O2D 1.48(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C11 H11 0.9300 . ?
C11D H11D 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.5(2) . . ?
C2 C1 H1 119.3 . . ?
C6 C1 H1 119.3 . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.5(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.63(19) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 117.73(16) . . ?
C5 C6 C7 123.40(15) . . ?
C1 C6 C7 118.80(15) . . ?
C6 C7 C8 110.25(13) . . ?
C6 C7 C14 115.44(12) . . ?
C8 C7 C14 111.36(12) . . ?
C6 C7 H7 106.4 . . ?
C8 C7 H7 106.4 . . ?
C14 C7 H7 106.4 . . ?
C13 C8 C9 117.75(17) . . ?
C13 C8 C7 120.29(16) . . ?
C9 C8 C7 121.94(15) . . ?
C8 C9 C10 120.8(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.4(4) . . ?
C11D C10 C9 119.6(11) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C11 C12 C13 120.2(4) . . ?
C11D C12 C13 119.2(11) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 121.2(2) . . ?
C8 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C18 C14 C15 102.63(12) . . ?
C18 C14 C7 115.05(13) . . ?
C15 C14 C7 114.81(12) . . ?
C18 C14 H14 108.0 . . ?
C15 C14 H14 108.0 . . ?
C7 C14 H14 108.0 . . ?
C14 C15 C16 104.65(12) . . ?
C14 C15 H15A 110.8 . . ?
C16 C15 H15A 110.8 . . ?
C14 C15 H15B 110.8 . . ?
C16 C15 H15B 110.8 . . ?
H15A C15 H15B 108.9 . . ?
C19 C16 C17 112.73(15) . . ?
C19 C16 C15 112.24(13) . . ?
C17 C16 C15 104.29(13) . . ?
C19 C16 H16 109.1 . . ?
C17 C16 H16 109.1 . . ?
C15 C16 H16 109.1 . . ?
C18 C17 C16 106.01(15) . . ?
C18 C17 H17A 110.5 . . ?
C16 C17 H17A 110.5 . . ?
C18 C17 H17B 110.5 . . ?
C16 C17 H17B 110.5 . . ?
H17A C17 H17B 108.7 . . ?
O1 C18 C17 123.35(16) . . ?
O1 C18 C14 126.86(15) . . ?
C17 C18 C14 109.73(14) . . ?
O3D C19 O2D 117.7(18) . . ?
O3 C19 O2 124.0(6) . . ?
O3 C19 C16 124.3(4) . . ?
O3D C19 C16 126.7(8) . . ?
O2D C19 C16 114.8(15) . . ?
O2 C19 C16 111.6(5) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C12 C11 C10 119.3(7) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C19 O2 C20 115.2(7) . . ?
C10 C11D C12 118.2(17) . . ?
C10 C11D H11D 120.9 . . ?
C12 C11D H11D 120.9 . . ?
C19 O2D C20 119(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 0.6(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 175.72(16) . . . . ?
C2 C1 C6 C5 0.5(3) . . . . ?
C2 C1 C6 C7 -176.42(17) . . . . ?
C5 C6 C7 C8 -86.35(19) . . . . ?
C1 C6 C7 C8 90.38(18) . . . . ?
C5 C6 C7 C14 40.9(2) . . . . ?
C1 C6 C7 C14 -142.37(15) . . . . ?
C6 C7 C8 C13 -127.32(16) . . . . ?
C14 C7 C8 C13 103.20(17) . . . . ?
C6 C7 C8 C9 51.0(2) . . . . ?
C14 C7 C8 C9 -78.50(19) . . . . ?
C13 C8 C9 C10 1.1(3) . . . . ?
C7 C8 C9 C10 -177.24(18) . . . . ?
C8 C9 C10 C11 3.2(7) . . . . ?
C8 C9 C10 C11D -11(2) . . . . ?
C9 C8 C13 C12 -1.1(3) . . . . ?
C7 C8 C13 C12 177.24(17) . . . . ?
C11 C12 C13 C8 -3.1(7) . . . . ?
C11D C12 C13 C8 11(2) . . . . ?
C6 C7 C14 C18 57.97(18) . . . . ?
C8 C7 C14 C18 -175.35(12) . . . . ?
C6 C7 C14 C15 176.78(13) . . . . ?
C8 C7 C14 C15 -56.54(17) . . . . ?
C18 C14 C15 C16 -34.26(15) . . . . ?
C7 C14 C15 C16 -159.82(13) . . . . ?
C14 C15 C16 C19 156.62(13) . . . . ?
C14 C15 C16 C17 34.28(17) . . . . ?
C19 C16 C17 C18 -142.42(16) . . . . ?
C15 C16 C17 C18 -20.4(2) . . . . ?
C16 C17 C18 O1 176.26(17) . . . . ?
C16 C17 C18 C14 -1.1(2) . . . . ?
C15 C14 C18 O1 -155.17(17) . . . . ?
C7 C14 C18 O1 -29.8(2) . . . . ?
C15 C14 C18 C17 22.02(18) . . . . ?
C7 C14 C18 C17 147.43(16) . . . . ?
C17 C16 C19 O3 0.8(5) . . . . ?
C15 C16 C19 O3 -116.6(5) . . . . ?
C17 C16 C19 O3D 34(2) . . . . ?
C15 C16 C19 O3D -83(2) . . . . ?
C17 C16 C19 O2D -155.9(18) . . . . ?
C15 C16 C19 O2D 86.7(18) . . . . ?
C17 C16 C19 O2 -176.6(5) . . . . ?
C15 C16 C19 O2 66.0(5) . . . . ?
C13 C12 C11 C10 7.4(13) . . . . ?
C9 C10 C11 C12 -7.4(13) . . . . ?
O3 C19 O2 C20 0.5(9) . . . . ?
C16 C19 O2 C20 178.0(5) . . . . ?
C9 C10 C11D C12 21(4) . . . . ?
C13 C12 C11D C10 -21(4) . . . . ?
O3D C19 O2D C20 10(3) . . . . ?
C16 C19 O2D C20 -160.9(17) . . . . ?

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.027



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
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# Please retain this information to preserve the provenance of 
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data_KB1657_0m
_database_code_depnum_ccdc_archive 'CCDC 2404674'
loop_
_audit_author_name
_audit_author_address
'Balasubramanian Sridhar'
;Senior Principal Scientist
India
;
_audit_update_record             
;
2024-11-22 deposited with the CCDC.	2025-03-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 N O3'
_chemical_formula_sum            'C22 H15 N O3'
_chemical_formula_weight         341.35

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                   9.2385(13)
_cell_length_b                   9.7060(12)
_cell_length_c                   10.2025(13)
_cell_angle_alpha                94.316(4)
_cell_angle_beta                 109.438(4)
_cell_angle_gamma                95.638(4)
_cell_volume                     852.83(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6086
_cell_measurement_theta_min      2.358
_cell_measurement_theta_max      27.6755

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6591
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16655
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_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         2.358
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4226
_reflns_number_gt                2924
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0489P)²+0.1381P] 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_number_reflns         4226
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1206
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.3133(2) 0.29629(17) 0.86015(17) 0.0625(4) Uani 1 1 d . . . . .
H1 H 0.325830 0.213254 0.900049 0.075 Uiso 1 1 calc R U . . .
C2 C 0.17152(19) 0.34511(19) 0.82224(17) 0.0665(5) Uani 1 1 d . . . . .
H2 H 0.088359 0.294681 0.836790 0.080 Uiso 1 1 calc R U . . .
C3 C 0.15212(18) 0.46770(18) 0.76311(17) 0.0613(4) Uani 1 1 d . . . . .
H3 H 0.056180 0.499929 0.738831 0.074 Uiso 1 1 calc R U . . .
C4 C 0.27378(16) 0.54344(16) 0.73943(16) 0.0523(4) Uani 1 1 d . . . . .
H4 H 0.259565 0.625932 0.698763 0.063 Uiso 1 1 calc R U . . .
C5 C 0.41807(15) 0.49576(13) 0.77673(13) 0.0413(3) Uani 1 1 d . . . . .
C6 C 0.43719(16) 0.37185(14) 0.83840(14) 0.0467(3) Uani 1 1 d . . . . .
C7 C 0.56645(14) 0.55671(13) 0.76640(13) 0.0399(3) Uani 1 1 d . . . . .
C8 C 0.68273(16) 0.46037(14) 0.83109(14) 0.0449(3) Uani 1 1 d . . . . .
C9 C 0.60033(17) 0.34077(15) 0.87593(16) 0.0536(4) Uani 1 1 d . . . . .
H9A H 0.604876 0.252800 0.826562 0.064 Uiso 1 1 calc R U . . .
H9B H 0.645992 0.336609 0.975777 0.064 Uiso 1 1 calc R U . . .
C10 C 0.59916(15) 0.66946(13) 0.70655(13) 0.0393(3) Uani 1 1 d . . . . .
C11 C 0.47988(15) 0.75390(13) 0.62656(14) 0.0406(3) Uani 1 1 d . . . . .
C12 C 0.36964(17) 0.69852(15) 0.49944(15) 0.0504(3) Uani 1 1 d . . . . .
H12 H 0.366678 0.606268 0.465457 0.061 Uiso 1 1 calc R U . . .
C13 C 0.26380(17) 0.77904(17) 0.42240(16) 0.0573(4) Uani 1 1 d . . . . .
H13 H 0.190588 0.740921 0.336899 0.069 Uiso 1 1 calc R U . . .
C14 C 0.26678(18) 0.91450(17) 0.47187(18) 0.0596(4) Uani 1 1 d . . . . .
H14 H 0.195734 0.968585 0.419967 0.072 Uiso 1 1 calc R U . . .
C15 C 0.37446(19) 0.97059(16) 0.59793(19) 0.0618(4) Uani 1 1 d . . . . .
H15 H 0.374983 1.062314 0.632010 0.074 Uiso 1 1 calc R U . . .
C16 C 0.48241(17) 0.89193(14) 0.67494(16) 0.0523(4) Uani 1 1 d . . . . .
H16 H 0.556769 0.931588 0.759249 0.063 Uiso 1 1 calc R U . . .
C17 C 0.75915(15) 0.72049(13) 0.71167(14) 0.0405(3) Uani 1 1 d . . . . .
C18 C 0.79409(17) 0.71993(15) 0.58968(15) 0.0498(3) Uani 1 1 d . . . . .
H18 H 0.718515 0.682930 0.505043 0.060 Uiso 1 1 calc R U . . .
C19 C 0.93898(18) 0.77326(17) 0.59135(17) 0.0579(4) Uani 1 1 d . . . . .
H19 H 0.960730 0.769821 0.508569 0.070 Uiso 1 1 calc R U . . .
C20 C 1.05122(17) 0.83144(15) 0.71490(18) 0.0544(4) Uani 1 1 d . . . . .
H20 H 1.148454 0.869402 0.716886 0.065 Uiso 1 1 calc R U . . .
C21 C 1.01552(15) 0.83183(13) 0.83538(15) 0.0449(3) Uani 1 1 d . . . . .
C22 C 0.87279(15) 0.77723(13) 0.83701(14) 0.0436(3) Uani 1 1 d . . . . .
H22 H 0.852922 0.778359 0.920633 0.052 Uiso 1 1 calc R U . . .
N1 N 1.13363(14) 0.89358(13) 0.96927(16) 0.0580(3) Uani 1 1 d . . . . .
O1 O 1.10537(14) 0.88450(12) 1.07708(13) 0.0710(3) Uani 1 1 d . . . . .
O2 O 1.25610(14) 0.95125(15) 0.96629(15) 0.0910(4) Uani 1 1 d . . . . .
O3 O 0.81727(12) 0.47204(11) 0.84113(13) 0.0630(3) Uani 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 C2 1.379(2) . ?
C1 C6 1.388(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.375(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.381(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.3950(19) . ?
C4 H4 0.9300 . ?
C5 C6 1.3982(19) . ?
C5 C7 1.4787(18) . ?
C6 C9 1.494(2) . ?
C7 C10 1.3491(18) . ?
C7 C8 1.5107(18) . ?
C8 O3 1.2059(16) . ?
C8 C9 1.5081(19) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.4939(18) . ?
C10 C17 1.4946(18) . ?
C11 C12 1.3844(19) . ?
C11 C16 1.3876(19) . ?
C12 C13 1.384(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.370(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.3857(19) . ?
C17 C22 1.3884(18) . ?
C18 C19 1.381(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.375(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.3778(18) . ?
C21 N1 1.4738(19) . ?
C22 H22 0.9300 . ?
N1 O1 1.2195(17) . ?
N1 O2 1.2229(17) . ?

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 119.58(15) . . ?
C2 C1 H1 120.2 . . ?
C6 C1 H1 120.2 . . ?
C3 C2 C1 120.54(14) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.62(15) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.76(14) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 119.21(13) . . ?
C4 C5 C7 130.91(12) . . ?
C6 C5 C7 109.86(12) . . ?
C1 C6 C5 120.29(14) . . ?
C1 C6 C9 128.24(13) . . ?
C5 C6 C9 111.46(12) . . ?
C10 C7 C5 130.14(12) . . ?
C10 C7 C8 123.84(12) . . ?
C5 C7 C8 105.93(10) . . ?
O3 C8 C9 124.84(13) . . ?
O3 C8 C7 126.79(13) . . ?
C9 C8 C7 108.31(11) . . ?
C6 C9 C8 104.43(11) . . ?
C6 C9 H9A 110.9 . . ?
C8 C9 H9A 110.9 . . ?
C6 C9 H9B 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C7 C10 C11 123.74(11) . . ?
C7 C10 C17 122.95(12) . . ?
C11 C10 C17 113.30(10) . . ?
C12 C11 C16 118.64(13) . . ?
C12 C11 C10 120.79(12) . . ?
C16 C11 C10 120.49(12) . . ?
C13 C12 C11 120.68(14) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.06(15) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.97(14) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.54(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.08(14) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
C18 C17 C22 118.67(12) . . ?
C18 C17 C10 120.39(12) . . ?
C22 C17 C10 120.83(12) . . ?
C19 C18 C17 121.27(14) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 120.28(14) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 118.06(13) . . ?
C21 C20 H20 121.0 . . ?
C19 C20 H20 121.0 . . ?
C20 C21 C22 122.84(13) . . ?
C20 C21 N1 119.20(13) . . ?
C22 C21 N1 117.96(13) . . ?
C21 C22 C17 118.86(13) . . ?
C21 C22 H22 120.6 . . ?
C17 C22 H22 120.6 . . ?
O1 N1 O2 123.24(14) . . ?
O1 N1 C21 118.89(12) . . ?
O2 N1 C21 117.87(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 -0.3(2) . . . . ?
C3 C4 C5 C7 -178.43(14) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C2 C1 C6 C9 177.67(15) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C7 C5 C6 C1 179.46(13) . . . . ?
C4 C5 C6 C9 -177.77(13) . . . . ?
C7 C5 C6 C9 0.71(16) . . . . ?
C4 C5 C7 C10 -6.6(2) . . . . ?
C6 C5 C7 C10 175.19(14) . . . . ?
C4 C5 C7 C8 176.92(14) . . . . ?
C6 C5 C7 C8 -1.32(14) . . . . ?
C10 C7 C8 O3 1.9(2) . . . . ?
C5 C7 C8 O3 178.69(14) . . . . ?
C10 C7 C8 C9 -175.35(13) . . . . ?
C5 C7 C8 C9 1.43(14) . . . . ?
C1 C6 C9 C8 -178.41(15) . . . . ?
C5 C6 C9 C8 0.21(16) . . . . ?
O3 C8 C9 C6 -178.34(14) . . . . ?
C7 C8 C9 C6 -1.02(15) . . . . ?
C5 C7 C10 C11 -4.2(2) . . . . ?
C8 C7 C10 C11 171.79(12) . . . . ?
C5 C7 C10 C17 177.08(12) . . . . ?
C8 C7 C10 C17 -7.0(2) . . . . ?
C7 C10 C11 C12 -67.80(18) . . . . ?
C17 C10 C11 C12 111.06(14) . . . . ?
C7 C10 C11 C16 115.52(15) . . . . ?
C17 C10 C11 C16 -65.62(16) . . . . ?
C16 C11 C12 C13 -0.2(2) . . . . ?
C10 C11 C12 C13 -176.95(13) . . . . ?
C11 C12 C13 C14 -0.3(2) . . . . ?
C12 C13 C14 C15 -0.1(2) . . . . ?
C13 C14 C15 C16 1.1(2) . . . . ?
C14 C15 C16 C11 -1.7(2) . . . . ?
C12 C11 C16 C15 1.2(2) . . . . ?
C10 C11 C16 C15 177.95(13) . . . . ?
C7 C10 C17 C18 116.12(15) . . . . ?
C11 C10 C17 C18 -62.75(16) . . . . ?
C7 C10 C17 C22 -67.92(17) . . . . ?
C11 C10 C17 C22 113.21(13) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
C10 C17 C18 C19 176.62(13) . . . . ?
C17 C18 C19 C20 -1.5(2) . . . . ?
C18 C19 C20 C21 1.4(2) . . . . ?
C19 C20 C21 C22 -0.3(2) . . . . ?
C19 C20 C21 N1 -179.97(12) . . . . ?
C20 C21 C22 C17 -0.7(2) . . . . ?
N1 C21 C22 C17 179.03(11) . . . . ?
C18 C17 C22 C21 0.52(19) . . . . ?
C10 C17 C22 C21 -175.51(12) . . . . ?
C20 C21 N1 O1 -174.64(13) . . . . ?
C22 C21 N1 O1 5.64(19) . . . . ?
C20 C21 N1 O2 5.1(2) . . . . ?
C22 C21 N1 O2 -174.64(13) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.031



