# Supplementary Information (SI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2025

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

data_KB845_0m
_database_code_depnum_ccdc_archive 'CCDC 2395429'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-11-02 deposited with the CCDC.	2025-01-15 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 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

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           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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                   12.1282(11)
_cell_length_b                   20.2533(17)
_cell_length_c                   7.5226(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.106(4)
_cell_angle_gamma                90
_cell_volume                     1847.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5725
_cell_measurement_theta_min      3.316
_cell_measurement_theta_max      22.558

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6477
_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
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17414
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_point_group_measured_fraction_full 0.945
_reflns_number_total             4227
_reflns_number_gt                2764
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.833
_reflns_Friedel_fraction_max     0.833
_reflns_Friedel_fraction_full    0.893

_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0480P)²+0.2142P] 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_abs_structure_details 
;
 Flack x determined using 1056 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4227
_refine_ls_number_parameters     240
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_restrained_S_all      0.998
_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
O1 O 0.5621(2) 0.92399(10) 0.4249(3) 0.0916(7) Uani 1 1 d . . . . .
O2 O 0.64657(16) 0.72996(10) 0.0479(2) 0.0686(5) Uani 1 1 d . . . . .
N1 N 0.6109(2) 0.83213(11) 0.2730(3) 0.0605(6) Uani 1 1 d . . . . .
H1N H 0.639(2) 0.8173(15) 0.170(5) 0.068(9) Uiso 1 1 d . . . . .
N2 N 0.6782(2) 0.85125(15) 0.7618(4) 0.0884(8) Uani 1 1 d . . . . .
C1 C 0.5664(2) 0.78227(13) 0.3751(3) 0.0543(6) Uani 1 1 d . . . . .
C2 C 0.5513(2) 0.72002(13) 0.3169(3) 0.0556(6) Uani 1 1 d . . . . .
C3 C 0.5074(3) 0.67649(15) 0.4617(4) 0.0713(8) Uani 1 1 d . . . . .
H3A H 0.545643 0.634452 0.465758 0.086 Uiso 1 1 calc R U . . .
H3B H 0.428973 0.668620 0.444748 0.086 Uiso 1 1 calc R U . . .
C4 C 0.5305(3) 0.71655(14) 0.6296(4) 0.0668(7) Uani 1 1 d . . . . .
H4A H 0.601443 0.704659 0.682105 0.080 Uiso 1 1 calc R U . . .
H4B H 0.473768 0.709006 0.716479 0.080 Uiso 1 1 calc R U . . .
C5 C 0.5304(2) 0.78982(13) 0.5686(3) 0.0576(6) Uani 1 1 d . . . . .
C6 C 0.6118(2) 0.82662(15) 0.6749(4) 0.0638(7) Uani 1 1 d . . . . .
C7 C 0.4127(2) 0.82030(16) 0.5789(4) 0.0651(7) Uani 1 1 d . . . . .
H7A H 0.406946 0.856665 0.495346 0.078 Uiso 1 1 calc R U . . .
H7B H 0.358999 0.787187 0.542871 0.078 Uiso 1 1 calc R U . . .
C8 C 0.3849(2) 0.84495(15) 0.7606(4) 0.0660(7) Uani 1 1 d . . . . .
C9 C 0.3439(2) 0.80430(19) 0.8919(4) 0.0797(9) Uani 1 1 d . . . . .
H9 H 0.330702 0.759949 0.867492 0.096 Uiso 1 1 calc R U . . .
C10 C 0.3222(3) 0.8294(3) 1.0608(5) 0.0991(12) Uani 1 1 d . . . . .
H10 H 0.297391 0.801519 1.149624 0.119 Uiso 1 1 calc R U . . .
C11 C 0.3375(3) 0.8948(3) 1.0951(5) 0.1055(13) Uani 1 1 d . . . . .
H11 H 0.321261 0.911843 1.206406 0.127 Uiso 1 1 calc R U . . .
C12 C 0.3765(4) 0.9350(2) 0.9671(6) 0.1105(13) Uani 1 1 d . . . . .
H12 H 0.386618 0.979645 0.990638 0.133 Uiso 1 1 calc R U . . .
C13 C 0.4010(3) 0.91042(19) 0.8039(5) 0.0889(10) Uani 1 1 d . . . . .
H13 H 0.429501 0.938749 0.718987 0.107 Uiso 1 1 calc R U . . .
C14 C 0.6066(3) 0.89964(14) 0.2989(4) 0.0669(7) Uani 1 1 d . . . . .
C15 C 0.6624(3) 0.93922(17) 0.1600(4) 0.0852(10) Uani 1 1 d . . . . .
H15A H 0.740083 0.930256 0.164360 0.128 Uiso 1 1 calc R U . . .
H15B H 0.650115 0.985357 0.181293 0.128 Uiso 1 1 calc R U . . .
H15C H 0.632799 0.927564 0.044963 0.128 Uiso 1 1 calc R U . . .
C16 C 0.5829(2) 0.69726(14) 0.1397(3) 0.0570(6) Uani 1 1 d . . . . .
C17 C 0.5391(2) 0.63401(13) 0.0695(3) 0.0600(7) Uani 1 1 d . . . . .
C18 C 0.6070(3) 0.59182(17) -0.0224(5) 0.0836(9) Uani 1 1 d . . . . .
H18 H 0.681218 0.601914 -0.034941 0.100 Uiso 1 1 calc R U . . .
C19 C 0.5640(5) 0.5346(2) -0.0955(6) 0.1120(14) Uani 1 1 d . . . . .
H19 H 0.609836 0.505350 -0.154310 0.134 Uiso 1 1 calc R U . . .
C20 C 0.4533(5) 0.52069(19) -0.0813(5) 0.1119(16) Uani 1 1 d . . . . .
H20 H 0.424903 0.482087 -0.131107 0.134 Uiso 1 1 calc R U . . .
C21 C 0.3847(4) 0.56283(18) 0.0048(5) 0.0905(11) Uani 1 1 d . . . . .
H21 H 0.309700 0.553811 0.010793 0.109 Uiso 1 1 calc R U . . .
C22 C 0.4279(3) 0.61893(15) 0.0829(4) 0.0689(8) Uani 1 1 d . . . . .
H22 H 0.381995 0.647038 0.145385 0.083 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.205(3) . ?
O2 C16 1.238(3) . ?
N1 C14 1.382(4) . ?
N1 C1 1.384(3) . ?
N1 H1N 0.90(3) . ?
N2 C6 1.143(4) . ?
C1 C2 1.346(3) . ?
C1 C5 1.535(4) . ?
C2 C16 1.468(4) . ?
C2 C3 1.506(4) . ?
C3 C4 1.523(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.554(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.462(4) . ?
C5 C7 1.558(4) . ?
C7 C8 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.378(5) . ?
C8 C9 1.385(4) . ?
C9 C10 1.399(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.361(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.353(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.363(5) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.489(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.480(4) . ?
C17 C18 1.381(4) . ?
C17 C22 1.388(4) . ?
C18 C19 1.381(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.364(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9300 . ?
C22 H22 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
C14 N1 C1 128.9(3) . . ?
C14 N1 H1N 117.8(19) . . ?
C1 N1 H1N 112.9(19) . . ?
C2 C1 N1 123.7(2) . . ?
C2 C1 C5 111.2(2) . . ?
N1 C1 C5 125.0(2) . . ?
C1 C2 C16 123.6(2) . . ?
C1 C2 C3 111.2(2) . . ?
C16 C2 C3 125.1(2) . . ?
C2 C3 C4 103.1(2) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C5 105.3(2) . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4B 110.7 . . ?
C5 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
C6 C5 C1 111.6(2) . . ?
C6 C5 C4 109.2(2) . . ?
C1 C5 C4 100.7(2) . . ?
C6 C5 C7 112.3(2) . . ?
C1 C5 C7 111.4(2) . . ?
C4 C5 C7 111.0(2) . . ?
N2 C6 C5 175.2(3) . . ?
C8 C7 C5 113.6(2) . . ?
C8 C7 H7A 108.9 . . ?
C5 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C5 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C13 C8 C9 117.0(3) . . ?
C13 C8 C7 120.1(3) . . ?
C9 C8 C7 122.8(3) . . ?
C8 C9 C10 120.5(4) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C12 C11 C10 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 122.1(4) . . ?
C12 C13 H13 119.0 . . ?
C8 C13 H13 119.0 . . ?
O1 C14 N1 122.3(3) . . ?
O1 C14 C15 123.2(3) . . ?
N1 C14 C15 114.5(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 C2 121.0(2) . . ?
O2 C16 C17 119.2(2) . . ?
C2 C16 C17 119.8(2) . . ?
C18 C17 C22 119.3(3) . . ?
C18 C17 C16 120.0(3) . . ?
C22 C17 C16 120.5(2) . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 119.2(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 H21 120.4 . . ?
C21 C22 C17 120.8(3) . . ?
C21 C22 H22 119.6 . . ?
C17 C22 H22 119.6 . . ?

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
C14 N1 C1 C2 162.8(3) . . . . ?
C14 N1 C1 C5 -18.5(4) . . . . ?
N1 C1 C2 C16 1.7(4) . . . . ?
C5 C1 C2 C16 -177.1(2) . . . . ?
N1 C1 C2 C3 176.9(3) . . . . ?
C5 C1 C2 C3 -1.9(3) . . . . ?
C1 C2 C3 C4 -16.3(3) . . . . ?
C16 C2 C3 C4 158.8(3) . . . . ?
C2 C3 C4 C5 27.4(3) . . . . ?
C2 C1 C5 C6 134.6(2) . . . . ?
N1 C1 C5 C6 -44.2(4) . . . . ?
C2 C1 C5 C4 18.8(3) . . . . ?
N1 C1 C5 C4 -160.0(3) . . . . ?
C2 C1 C5 C7 -99.0(3) . . . . ?
N1 C1 C5 C7 82.2(3) . . . . ?
C3 C4 C5 C6 -145.4(3) . . . . ?
C3 C4 C5 C1 -27.9(3) . . . . ?
C3 C4 C5 C7 90.2(3) . . . . ?
C6 C5 C7 C8 -39.0(3) . . . . ?
C1 C5 C7 C8 -165.0(2) . . . . ?
C4 C5 C7 C8 83.5(3) . . . . ?
C5 C7 C8 C13 94.8(3) . . . . ?
C5 C7 C8 C9 -84.4(3) . . . . ?
C13 C8 C9 C10 -1.1(5) . . . . ?
C7 C8 C9 C10 178.2(3) . . . . ?
C8 C9 C10 C11 2.4(6) . . . . ?
C9 C10 C11 C12 -1.8(6) . . . . ?
C10 C11 C12 C13 -0.3(7) . . . . ?
C11 C12 C13 C8 1.7(7) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C7 C8 C13 C12 179.8(4) . . . . ?
C1 N1 C14 O1 1.7(5) . . . . ?
C1 N1 C14 C15 -179.0(3) . . . . ?
C1 C2 C16 O2 15.8(4) . . . . ?
C3 C2 C16 O2 -158.7(3) . . . . ?
C1 C2 C16 C17 -164.7(3) . . . . ?
C3 C2 C16 C17 20.8(4) . . . . ?
O2 C16 C17 C18 40.3(4) . . . . ?
C2 C16 C17 C18 -139.2(3) . . . . ?
O2 C16 C17 C22 -134.6(3) . . . . ?
C2 C16 C17 C22 45.9(4) . . . . ?
C22 C17 C18 C19 -1.6(5) . . . . ?
C16 C17 C18 C19 -176.6(3) . . . . ?
C17 C18 C19 C20 2.0(6) . . . . ?
C18 C19 C20 C21 -0.2(7) . . . . ?
C19 C20 C21 C22 -1.9(6) . . . . ?
C20 C21 C22 C17 2.2(5) . . . . ?
C18 C17 C22 C21 -0.5(4) . . . . ?
C16 C17 C22 C21 174.5(3) . . . . ?

_refine_diff_density_max         0.092
_refine_diff_density_min         -0.113
_refine_diff_density_rms         0.025

####################################################################### 
# 
# 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 
# 
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# Please retain this information to preserve the provenance of 
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data_KB1655_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2396659'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2024-11-04 deposited with the CCDC.	2025-01-15 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         'C19 H20 O3'
_chemical_formula_sum            'C19 H20 O3'
_chemical_formula_weight         296.35

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'
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                   12.6120(14)
_cell_length_b                   5.6910(6)
_cell_length_c                   22.766(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.590(5)
_cell_angle_gamma                90
_cell_volume                     1588.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    7654
_cell_measurement_theta_min      2.170
_cell_measurement_theta_max      28.801

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.083
_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  0.6837
_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
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON III C7 HPAD'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26864
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.170
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3649
_reflns_number_gt                2251
_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0655P)²+0.4172P] 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         3649
_refine_ls_number_parameters     220
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1630
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.042
_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
O3 O 0.84873(14) 0.7871(3) 0.42728(9) 0.0898(6) Uani 1 1 d . . . . .
C1 C 0.50870(16) 0.1121(4) 0.41931(10) 0.0585(5) Uani 1 1 d . . . . .
C2 C 0.52201(15) 0.1961(4) 0.35767(9) 0.0585(5) Uani 1 1 d . . . . .
H2 H 0.491088 0.354349 0.350194 0.070 Uiso 1 1 calc R U . . .
C3 C 0.46136(16) 0.0321(4) 0.30751(9) 0.0619(5) Uani 1 1 d . . . . .
H3A H 0.484371 0.067239 0.270694 0.074 Uiso 1 1 calc R U . . .
H3B H 0.482532 -0.128614 0.318726 0.074 Uiso 1 1 calc R U . . .
C4 C 0.33886(16) 0.0496(3) 0.29464(8) 0.0543(5) Uani 1 1 d . . . . .
C5 C 0.27650(17) -0.1177(4) 0.31418(9) 0.0625(5) Uani 1 1 d . . . . .
H5 H 0.310414 -0.245054 0.336517 0.075 Uiso 1 1 calc R U . . .
C6 C 0.16418(18) -0.0995(4) 0.30117(10) 0.0694(6) Uani 1 1 d . . . . .
H6 H 0.123509 -0.213458 0.315298 0.083 Uiso 1 1 calc R U . . .
C7 C 0.11214(18) 0.0845(4) 0.26770(11) 0.0724(6) Uani 1 1 d . . . . .
H7 H 0.036412 0.094149 0.258480 0.087 Uiso 1 1 calc R U . . .
C8 C 0.1724(2) 0.2546(4) 0.24785(11) 0.0726(6) Uani 1 1 d . . . . .
H8 H 0.137676 0.380695 0.225284 0.087 Uiso 1 1 calc R U . . .
C9 C 0.28439(19) 0.2383(4) 0.26140(10) 0.0667(6) Uani 1 1 d . . . . .
H9 H 0.324694 0.355347 0.248166 0.080 Uiso 1 1 calc R U . . .
C10 C 0.64398(16) 0.2060(4) 0.35695(11) 0.0644(5) Uani 1 1 d . . . . .
H10A H 0.679567 0.067008 0.377098 0.077 Uiso 1 1 calc R U . . .
H10B H 0.650049 0.200259 0.315286 0.077 Uiso 1 1 calc R U . . .
C11 C 0.70448(16) 0.4199(4) 0.38661(10) 0.0609(5) Uani 1 1 d . . . . .
H9A H 0.695708 0.433301 0.427682 0.073 Uiso 1 1 calc R U . . .
H9B H 0.674084 0.559813 0.364673 0.073 Uiso 1 1 calc R U . . .
C12 C 0.82550(16) 0.4017(3) 0.38738(9) 0.0579(5) Uani 1 1 d . . . . .
H12A H 0.855283 0.263907 0.410516 0.069 Uiso 1 1 calc R U . . .
H12B H 0.832814 0.378785 0.346298 0.069 Uiso 1 1 calc R U . . .
C13 C 0.89150(17) 0.6104(3) 0.41339(9) 0.0575(5) Uani 1 1 d . . . . .
C14 C 1.01299(16) 0.5997(3) 0.42218(8) 0.0515(4) Uani 1 1 d . . . . .
C15 C 1.06654(17) 0.4096(3) 0.40360(9) 0.0601(5) Uani 1 1 d . . . . .
H15 H 1.026391 0.283446 0.383964 0.072 Uiso 1 1 calc R U . . .
C16 C 1.17922(18) 0.4073(4) 0.41422(10) 0.0665(6) Uani 1 1 d . . . . .
H16 H 1.214308 0.280220 0.401401 0.080 Uiso 1 1 calc R U . . .
C17 C 1.23918(18) 0.5907(4) 0.44340(10) 0.0684(6) Uani 1 1 d . . . . .
H17 H 1.314913 0.586712 0.451078 0.082 Uiso 1 1 calc R U . . .
C18 C 1.1877(2) 0.7807(4) 0.46141(10) 0.0692(6) Uani 1 1 d . . . . .
H18 H 1.228686 0.906500 0.480662 0.083 Uiso 1 1 calc R U . . .
C19 C 1.07571(19) 0.7860(4) 0.45108(9) 0.0607(5) Uani 1 1 d . . . . .
H19 H 1.041593 0.915305 0.463544 0.073 Uiso 1 1 calc R U . . .
O1 O 0.4957(12) 0.268(3) 0.4581(6) 0.070(2) Uani 0.56(3) 1 d . U P A 1
H1O H 0.476942 0.203930 0.486292 0.106 Uiso 0.56(3) 1 calc R U P A 1
O2 O 0.5114(10) -0.0968(15) 0.4297(4) 0.0703(18) Uani 0.56(3) 1 d . U P A 1
O1D O 0.4673(15) 0.253(4) 0.4481(9) 0.083(3) Uani 0.44(3) 1 d . U P A 2
O2D O 0.5464(14) -0.097(3) 0.4402(8) 0.090(3) Uani 0.44(3) 1 d . U P A 2
H2D H 0.509161 -0.148244 0.462385 0.135 Uiso 0.44(3) 1 calc R U 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
O3 C13 1.217(2) . ?
C1 O2 1.212(9) . ?
C1 O1D 1.23(2) . ?
C1 O1 1.291(15) . ?
C1 O2D 1.326(14) . ?
C1 C2 1.529(3) . ?
C2 C3 1.533(3) . ?
C2 C10 1.543(3) . ?
C2 H2 0.9800 . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.374(3) . ?
C4 C9 1.398(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.376(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.526(3) . ?
C11 H9A 0.9700 . ?
C11 H9B 0.9700 . ?
C12 C13 1.491(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.499(3) . ?
C14 C19 1.392(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.373(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
O1 H1O 0.8200 . ?
O2D H2D 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
O2 C1 O1 123.0(8) . . ?
O1D C1 O2D 123.8(11) . . ?
O2 C1 C2 118.8(5) . . ?
O1D C1 C2 116.0(10) . . ?
O1 C1 C2 118.2(6) . . ?
O2D C1 C2 120.2(7) . . ?
C1 C2 C3 110.50(17) . . ?
C1 C2 C10 110.23(17) . . ?
C3 C2 C10 109.78(16) . . ?
C1 C2 H2 108.8 . . ?
C3 C2 H2 108.8 . . ?
C10 C2 H2 108.8 . . ?
C4 C3 C2 114.45(16) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C5 C4 C9 117.50(19) . . ?
C5 C4 C3 122.03(19) . . ?
C9 C4 C3 120.47(18) . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 119.5(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C8 C9 C4 121.4(2) . . ?
C8 C9 H9 119.3 . . ?
C4 C9 H9 119.3 . . ?
C11 C10 C2 115.16(17) . . ?
C11 C10 H10A 108.5 . . ?
C2 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C2 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C10 C11 C12 110.49(17) . . ?
C10 C11 H9A 109.6 . . ?
C12 C11 H9A 109.6 . . ?
C10 C11 H9B 109.6 . . ?
C12 C11 H9B 109.6 . . ?
H9A C11 H9B 108.1 . . ?
C13 C12 C11 114.49(17) . . ?
C13 C12 H12A 108.6 . . ?
C11 C12 H12A 108.6 . . ?
C13 C12 H12B 108.6 . . ?
C11 C12 H12B 108.6 . . ?
H12A C12 H12B 107.6 . . ?
O3 C13 C12 121.40(19) . . ?
O3 C13 C14 120.00(19) . . ?
C12 C13 C14 118.59(17) . . ?
C19 C14 C15 118.23(19) . . ?
C19 C14 C13 118.80(18) . . ?
C15 C14 C13 122.97(18) . . ?
C16 C15 C14 120.3(2) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.0(2) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.3(2) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.7(2) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C1 O1 H1O 109.5 . . ?
C1 O2D H2D 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
O2 C1 C2 C3 39.3(7) . . . . ?
O1D C1 C2 C3 -121.6(10) . . . . ?
O1 C1 C2 C3 -141.1(8) . . . . ?
O2D C1 C2 C3 62.0(10) . . . . ?
O2 C1 C2 C10 -82.2(7) . . . . ?
O1D C1 C2 C10 116.8(10) . . . . ?
O1 C1 C2 C10 97.4(8) . . . . ?
O2D C1 C2 C10 -59.5(10) . . . . ?
C1 C2 C3 C4 71.2(2) . . . . ?
C10 C2 C3 C4 -167.00(18) . . . . ?
C2 C3 C4 C5 -103.8(2) . . . . ?
C2 C3 C4 C9 76.8(2) . . . . ?
C9 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C6 -179.15(19) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C8 -1.2(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C4 0.7(4) . . . . ?
C5 C4 C9 C8 -1.0(3) . . . . ?
C3 C4 C9 C8 178.4(2) . . . . ?
C1 C2 C10 C11 -79.7(2) . . . . ?
C3 C2 C10 C11 158.40(18) . . . . ?
C2 C10 C11 C12 175.77(18) . . . . ?
C10 C11 C12 C13 177.39(18) . . . . ?
C11 C12 C13 O3 -6.5(3) . . . . ?
C11 C12 C13 C14 173.68(16) . . . . ?
O3 C13 C14 C19 5.5(3) . . . . ?
C12 C13 C14 C19 -174.67(18) . . . . ?
O3 C13 C14 C15 -175.6(2) . . . . ?
C12 C13 C14 C15 4.2(3) . . . . ?
C19 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C16 -178.49(19) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C16 C17 C18 C19 1.1(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
C15 C14 C19 C18 -0.6(3) . . . . ?
C13 C14 C19 C18 178.39(19) . . . . ?

_refine_diff_density_max         0.213
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.032

