# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

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

data_kpk_227_as_073_0m
_audit_block_doi                 10.5517/ccdc.csd.cc2pb44b
_database_code_depnum_ccdc_archive 'CCDC 2482391'
loop_
_audit_author_name
_audit_author_address
'Anisha Suresh'
;PhD Scholar
India
;
_audit_update_record             
;
2025-08-23 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2025-03-04
_audit_creation_method           
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
darshansmhatre@chem.iitb.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 O3'
_chemical_formula_sum            'C15 H18 O3'
_chemical_formula_weight         246.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.8030(10)
_cell_length_b                   10.3295(12)
_cell_length_c                   12.6647(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1282.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4162
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      23.24
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.5049
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1344 before and 0.0744 after correction.
The Ratio of minimum to maximum transmission is 0.6775.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13354
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.045
_diffrn_reflns_theta_max         25.045
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1955
_reflns_number_total             2265
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 730 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2265
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0442P)²+0.1230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15), C11(H11), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2)
2.d X=CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.e Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.09127(19) 0.4386(2) 0.64615(16) 0.0572(6) Uani 1 1 d . . . . .
O2 O 0.19980(16) 0.37884(19) 0.79340(13) 0.0433(5) Uani 1 1 d . . . . .
O3 O 0.86391(19) 0.55475(19) 0.76514(18) 0.0548(6) Uani 1 1 d . . . . .
H3 H 0.929538 0.537376 0.724921 0.082 Uiso 1 1 calc R U . . .
C4 C 0.8397(3) 0.2367(3) 0.7540(2) 0.0473(7) Uani 1 1 d . . . . .
H4A H 0.791091 0.166821 0.723022 0.057 Uiso 1 1 calc R U . . .
H4B H 0.936182 0.232542 0.760363 0.057 Uiso 1 1 calc R U . . .
C1 C 0.7666(3) 0.5036(3) 0.9311(2) 0.0489(8) Uani 1 1 d . . . . .
H1 H 0.808321 0.568661 0.973142 0.059 Uiso 1 1 calc R U . . .
C2 C 0.6439(3) 0.4651(3) 0.9571(2) 0.0452(7) Uani 1 1 d . . . . .
H2 H 0.603330 0.502432 1.018033 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5627(3) 0.3654(3) 0.89703(18) 0.0349(6) Uani 1 1 d . . . . .
C15 C 0.6221(2) 0.3586(2) 0.78321(18) 0.0310(6) Uani 1 1 d . . . . .
H15 H 0.607453 0.446199 0.751483 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5433(2) 0.2635(3) 0.7137(2) 0.0371(6) Uani 1 1 d . . . . .
H5A H 0.579397 0.265160 0.640719 0.044 Uiso 1 1 calc R U . . .
H5B H 0.552555 0.174380 0.741648 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3979(2) 0.3038(2) 0.71469(19) 0.0341(6) Uani 1 1 d . . . . .
C7 C 0.3173(3) 0.3457(3) 0.63749(19) 0.0378(6) Uani 1 1 d . . . . .
C8 C 0.3398(3) 0.3528(3) 0.5213(2) 0.0509(8) Uani 1 1 d . . . . .
H8A H 0.357965 0.442691 0.500988 0.076 Uiso 1 1 calc R U . . .
H8B H 0.258140 0.321780 0.484506 0.076 Uiso 1 1 calc R U . . .
H8C H 0.417954 0.298607 0.502050 0.076 Uiso 1 1 calc R U . . .
C9 C 0.5752(3) 0.2346(3) 0.9553(2) 0.0508(8) Uani 1 1 d . . . . .
H9A H 0.670095 0.204904 0.952749 0.076 Uiso 1 1 calc R U . . .
H9B H 0.516289 0.170484 0.921035 0.076 Uiso 1 1 calc R U . . .
H9C H 0.547143 0.245415 1.029026 0.076 Uiso 1 1 calc R U . . .
C10 C 0.1914(3) 0.3915(3) 0.6869(2) 0.0412(6) Uani 1 1 d . . . . .
C11 C 0.3297(2) 0.3203(3) 0.81908(19) 0.0366(6) Uani 1 1 d . . . . .
H11 H 0.314825 0.233796 0.852677 0.044 Uiso 1 1 calc R U . . .
C12 C 0.4126(2) 0.4062(3) 0.89217(19) 0.0354(6) Uani 1 1 d . . . . .
H12A H 0.373039 0.402452 0.964038 0.042 Uiso 1 1 calc R U . . .
H12B H 0.406735 0.496885 0.867287 0.042 Uiso 1 1 calc R U . . .
C13 C 0.7732(2) 0.3396(3) 0.78830(18) 0.0344(6) Uani 1 1 d . . . . .
C14 C 0.8455(3) 0.4514(3) 0.8389(2) 0.0414(7) Uani 1 1 d . . . . .
H14 H 0.936979 0.421679 0.864128 0.050 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 C10 1.211(3) . ?
O2 C10 1.358(3) . ?
O2 C11 1.447(3) . ?
O3 H3 0.8400 . ?
O3 C14 1.431(3) . ?
C4 H4A 0.9500 . ?
C4 H4B 0.9500 . ?
C4 C13 1.320(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.309(4) . ?
C1 C14 1.500(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.507(4) . ?
C3 C15 1.556(3) . ?
C3 C9 1.544(4) . ?
C3 C12 1.533(4) . ?
C15 H15 1.0000 . ?
C15 C5 1.529(3) . ?
C15 C13 1.496(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.485(3) . ?
C6 C7 1.329(3) . ?
C6 C11 1.491(3) . ?
C7 C8 1.489(3) . ?
C7 C10 1.463(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11 1.0000 . ?
C11 C12 1.518(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.499(4) . ?
C14 H14 1.0000 . ?

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
C10 O2 C11 108.49(19) . . ?
C14 O3 H3 109.5 . . ?
H4A C4 H4B 120.0 . . ?
C13 C4 H4A 120.0 . . ?
C13 C4 H4B 120.0 . . ?
C2 C1 H1 118.0 . . ?
C2 C1 C14 124.1(3) . . ?
C14 C1 H1 118.0 . . ?
C1 C2 H2 117.8 . . ?
C1 C2 C3 124.4(3) . . ?
C3 C2 H2 117.8 . . ?
C2 C3 C15 107.5(2) . . ?
C2 C3 C9 108.3(2) . . ?
C2 C3 C12 109.9(2) . . ?
C9 C3 C15 111.9(2) . . ?
C12 C3 C15 109.52(19) . . ?
C12 C3 C9 109.6(2) . . ?
C3 C15 H15 106.1 . . ?
C5 C15 C3 111.9(2) . . ?
C5 C15 H15 106.1 . . ?
C13 C15 C3 109.64(19) . . ?
C13 C15 H15 106.1 . . ?
C13 C15 C5 116.1(2) . . ?
C15 C5 H5A 110.2 . . ?
C15 C5 H5B 110.2 . . ?
H5A C5 H5B 108.5 . . ?
C6 C5 C15 107.4(2) . . ?
C6 C5 H5A 110.2 . . ?
C6 C5 H5B 110.2 . . ?
C5 C6 C11 118.0(2) . . ?
C7 C6 C5 131.0(2) . . ?
C7 C6 C11 110.4(2) . . ?
C6 C7 C8 130.9(3) . . ?
C6 C7 C10 107.0(2) . . ?
C10 C7 C8 122.1(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 O2 120.8(2) . . ?
O1 C10 C7 129.2(2) . . ?
O2 C10 C7 110.0(2) . . ?
O2 C11 C6 104.06(19) . . ?
O2 C11 H11 109.9 . . ?
O2 C11 C12 111.3(2) . . ?
C6 C11 H11 109.9 . . ?
C6 C11 C12 111.6(2) . . ?
C12 C11 H11 109.9 . . ?
C3 C12 H12A 109.2 . . ?
C3 C12 H12B 109.2 . . ?
C11 C12 C3 112.2(2) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C4 C13 C15 125.5(3) . . ?
C4 C13 C14 121.8(2) . . ?
C15 C13 C14 112.7(2) . . ?
O3 C14 C1 107.7(2) . . ?
O3 C14 C13 110.8(2) . . ?
O3 C14 H14 108.9 . . ?
C1 C14 H14 108.9 . . ?
C13 C14 C1 111.5(2) . . ?
C13 C14 H14 108.9 . . ?

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 C11 C12 C3 -164.73(19) . . . . ?
C4 C13 C14 O3 99.9(3) . . . . ?
C4 C13 C14 C1 -140.1(3) . . . . ?
C1 C2 C3 C15 -21.2(4) . . . . ?
C1 C2 C3 C9 100.0(3) . . . . ?
C1 C2 C3 C12 -140.3(3) . . . . ?
C2 C1 C14 O3 115.3(3) . . . . ?
C2 C1 C14 C13 -6.5(4) . . . . ?
C2 C3 C15 C5 -177.9(2) . . . . ?
C2 C3 C15 C13 51.7(3) . . . . ?
C2 C3 C12 C11 171.5(2) . . . . ?
C3 C15 C5 C6 56.3(3) . . . . ?
C3 C15 C13 C4 115.5(3) . . . . ?
C3 C15 C13 C14 -63.8(3) . . . . ?
C15 C3 C12 C11 53.6(3) . . . . ?
C15 C5 C6 C7 116.2(3) . . . . ?
C15 C5 C6 C11 -53.8(3) . . . . ?
C15 C13 C14 O3 -80.8(3) . . . . ?
C15 C13 C14 C1 39.2(3) . . . . ?
C5 C15 C13 C4 -12.6(4) . . . . ?
C5 C15 C13 C14 168.1(2) . . . . ?
C5 C6 C7 C8 7.8(5) . . . . ?
C5 C6 C7 C10 -170.8(3) . . . . ?
C5 C6 C11 O2 171.1(2) . . . . ?
C5 C6 C11 C12 51.0(3) . . . . ?
C6 C7 C10 O1 179.1(3) . . . . ?
C6 C7 C10 O2 1.3(3) . . . . ?
C6 C11 C12 C3 -49.0(3) . . . . ?
C7 C6 C11 O2 -0.8(3) . . . . ?
C7 C6 C11 C12 -120.9(3) . . . . ?
C8 C7 C10 O1 0.4(5) . . . . ?
C8 C7 C10 O2 -177.4(3) . . . . ?
C9 C3 C15 C5 63.2(3) . . . . ?
C9 C3 C15 C13 -67.1(3) . . . . ?
C9 C3 C12 C11 -69.5(3) . . . . ?
C10 O2 C11 C6 1.6(3) . . . . ?
C10 O2 C11 C12 121.9(2) . . . . ?
C11 O2 C10 O1 -179.9(3) . . . . ?
C11 O2 C10 C7 -1.9(3) . . . . ?
C11 C6 C7 C8 178.4(3) . . . . ?
C11 C6 C7 C10 -0.2(3) . . . . ?
C12 C3 C15 C5 -58.5(3) . . . . ?
C12 C3 C15 C13 171.1(2) . . . . ?
C13 C15 C5 C6 -176.7(2) . . . . ?
C14 C1 C2 C3 -1.6(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kpk_227_as_115_autored
_database_code_depnum_ccdc_archive 'CCDC 2504591'
loop_
_audit_author_name
_audit_author_address
'Mhatre D.S.'
;PhD research scholar 
India
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2025-11-21
_audit_creation_method           
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
darshansmhatre@chem.iitb.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H23 Br O4)'
_chemical_formula_sum            'C44 H46 Br2 O8'
_chemical_formula_weight         862.63
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.2933(3)
_cell_length_b                   14.1291(5)
_cell_length_c                   19.7449(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.884(3)
_cell_angle_gamma                90
_cell_volume                     2023.95(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4276
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      20.4620
_cell_measurement_theta_min      1.7720
_shelx_estimated_absorpt_T_max   0.845
_shelx_estimated_absorpt_T_min   0.684
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.085
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.0887
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30518
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.775
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -127.56  18.44   2.00    3.00    --  -22.85 -59.25  20.08   73
  2  ω   -127.56  18.44   2.00    3.00    --  -22.85 -59.25-135.92   73
  3  ω   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 122.08   73
  4  ω   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 -33.92   73
  5  ω   -127.56  18.44   2.00    3.00    --  -22.85 -59.25 173.08   73
  6  ω   -115.56  18.44   2.00    3.00    --  -22.85 -59.25 -84.92   67
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0312391000
_diffrn_orient_matrix_UB_12      0.0128275000
_diffrn_orient_matrix_UB_13      0.0315970000
_diffrn_orient_matrix_UB_21      0.0132873000
_diffrn_orient_matrix_UB_22      0.0484396000
_diffrn_orient_matrix_UB_23      -0.0074831000
_diffrn_orient_matrix_UB_31      -0.0917241000
_diffrn_orient_matrix_UB_32      0.0026798000
_diffrn_orient_matrix_UB_33      -0.0158142000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4400
_reflns_number_total             7130
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection       
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 
;
 Flack x determined using 1428 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7130
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0591
_refine_ls_restrained_S_all      1.444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+0.0640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(Br02) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.001
3.a Ternary CH refined with riding coordinates:
 C00E(H00G), C00L(H00L), C00N(H00N), C00Z(H00Z)
3.b Secondary CH2 refined with riding coordinates:
 C00F(H00H,H00I), C00S(H00P,H00Q), C00X(H00C,H00D), C00Y(H00E,H00F), C013(H01O,
 H01P), C01E(H01I,H01J)
3.c Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00U(H00U), C015(H015), C016(H016), C019(H019), C01A(H01D),
 C01C(H01E), C01F(H01K), C01G(H01T), C01H(H01L)
3.d X=CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00T(H00R,H00S), C012(H01M,H01N), C1(H1A,H1B)
3.e Idealised Me refined as rotating group:
 C00P(H00K,H00M,H00O), C017(H01A,H01B,H01C), C018(H01Q,H01R,H01S), C01D(H01F,
 H01G,H01H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 1.43510(19) 0.10907(9) 0.69955(6) 0.0886(4) Uani 1 1 d . . . . .
Br02 Br 0.7587(3) 1.00278(11) 0.49228(7) 0.1123(6) Uani 1 1 d . U . . .
O003 O -0.2167(9) 0.4459(4) 0.0867(3) 0.0484(15) Uani 1 1 d . . . . .
O004 O 0.2901(8) 0.0995(5) 0.1547(3) 0.0571(16) Uani 1 1 d . . . . .
O005 O 0.2142(9) 0.8784(5) 0.2065(3) 0.0586(18) Uani 1 1 d . . . . .
O006 O 0.8642(10) 0.3061(6) 0.4451(3) 0.070(2) Uani 1 1 d . . . . .
O007 O 0.0001(10) 0.3343(4) 0.0919(3) 0.0622(19) Uani 1 1 d . . . . .
O008 O 0.4656(10) -0.0033(5) 0.1046(3) 0.0686(19) Uani 1 1 d . . . . .
C009 C 0.0623(11) 0.4930(6) 0.0515(4) 0.040(2) Uani 1 1 d . . . . .
C00A C -0.0440(12) 0.4142(6) 0.0779(4) 0.041(2) Uani 1 1 d . . . . .
C00B C -0.2853(11) 0.7150(6) 0.0893(4) 0.0388(19) Uani 1 1 d . . . . .
C00C C -0.0496(12) 0.5671(6) 0.0423(4) 0.039(2) Uani 1 1 d . . . . .
O00D O 0.6442(11) 0.2682(7) 0.5124(4) 0.084(2) Uani 1 1 d . . . . .
C00E C -0.0856(11) 0.7397(6) 0.0717(4) 0.040(2) Uani 1 1 d . . . . .
H00G H -0.097730 0.801047 0.046279 0.048 Uiso 1 1 calc R U . . .
C00F C -0.2944(10) 0.6108(6) 0.1142(4) 0.0402(18) Uani 1 1 d . . . . .
H00H H -0.212833 0.603197 0.157121 0.048 Uiso 1 1 calc R U . . .
H00I H -0.421900 0.595876 0.123647 0.048 Uiso 1 1 calc R U . . .
O00G O -0.0104(12) 0.9359(8) 0.2650(4) 0.103(3) Uani 1 1 d . . . . .
C00H C 0.5165(12) 0.2144(6) 0.1811(4) 0.044(2) Uani 1 1 d . . . . .
C00I C 0.4509(14) 0.0693(7) 0.1346(5) 0.052(2) Uani 1 1 d . . . . .
C00J C -0.4157(13) 0.7281(7) 0.0237(5) 0.055(3) Uani 1 1 d . . . . .
H00J H -0.390293 0.688806 -0.013260 0.066 Uiso 1 1 calc R U . . .
C00K C 0.5958(12) 0.1406(6) 0.1542(4) 0.043(2) Uani 1 1 d . . . . .
C00L C 0.3159(13) 0.1935(6) 0.1841(4) 0.048(2) Uani 1 1 d . . . . .
H00L H 0.238975 0.240444 0.155958 0.058 Uiso 1 1 calc R U . . .
C00M C 0.0517(11) 0.7586(6) 0.1333(4) 0.039(2) Uani 1 1 d . . . . .
C00N C -0.2358(11) 0.5426(5) 0.0617(4) 0.039(2) Uani 1 1 d . . . . .
H00N H -0.327170 0.544403 0.020352 0.047 Uiso 1 1 calc R U . . .
C00O C 0.3220(14) 0.2960(8) 0.2898(4) 0.059(3) Uani 1 1 d . . . . .
C00P C -0.3451(13) 0.7801(7) 0.1453(4) 0.050(2) Uani 1 1 d . . . . .
H00K H -0.261874 0.771396 0.187002 0.075 Uiso 1 1 calc R U . . .
H00M H -0.471298 0.764243 0.154134 0.075 Uiso 1 1 calc R U . . .
H00O H -0.340405 0.846108 0.130378 0.075 Uiso 1 1 calc R U . . .
C00Q C 0.7301(14) 0.1898(8) 0.3361(5) 0.062(3) Uani 1 1 d . . . . .
H00A H 0.822655 0.169157 0.370258 0.074 Uiso 1 1 calc R U . . .
H00B H 0.685945 0.148196 0.300300 0.074 Uiso 1 1 calc R U . . .
C00R C 0.9595(15) 0.2348(7) 0.5500(4) 0.057(3) Uani 1 1 d . . . . .
C00S C -0.0134(12) 0.6677(6) 0.0215(4) 0.043(2) Uani 1 1 d . . . . .
H00P H -0.074638 0.679320 -0.024819 0.051 Uiso 1 1 calc R U . . .
H00Q H 0.120795 0.676930 0.020277 0.051 Uiso 1 1 calc R U . . .
C00T C 0.1405(11) 0.6920(7) 0.1717(4) 0.047(2) Uani 1 1 d . . . . .
H00R H 0.227328 0.709512 0.208703 0.056 Uiso 1 1 calc R U . . .
H00S H 0.116944 0.627021 0.161916 0.056 Uiso 1 1 calc R U . . .
C00U C 0.4834(15) 0.9162(8) 0.3091(5) 0.065(3) Uani 1 1 d . . . . .
H00U H 0.515639 0.890723 0.267431 0.078 Uiso 1 1 calc R U . . .
C00V C 0.3003(15) 0.9341(7) 0.3171(5) 0.057(3) Uani 1 1 d . . . . .
C00W C 1.2418(17) 0.1604(7) 0.6396(4) 0.060(3) Uani 1 1 d . . . . .
C00X C 0.2717(13) 0.1981(7) 0.2583(4) 0.055(2) Uani 1 1 d . . . . .
H00C H 0.341667 0.148336 0.285066 0.066 Uiso 1 1 calc R U . . .
H00D H 0.138666 0.186002 0.260226 0.066 Uiso 1 1 calc R U . . .
C00Y C 0.5869(14) 0.3063(6) 0.2104(4) 0.050(2) Uani 1 1 d . . . . .
H00E H 0.537337 0.358724 0.180678 0.060 Uiso 1 1 calc R U . . .
H00F H 0.722967 0.307566 0.211927 0.060 Uiso 1 1 calc R U . . .
C00Z C 0.5299(13) 0.3218(7) 0.2840(4) 0.048(2) Uani 1 1 d . . . . .
H00Z H 0.540005 0.391432 0.292472 0.057 Uiso 1 1 calc R U . . .
C010 C 0.1490(17) 0.9167(8) 0.2613(6) 0.066(3) Uani 1 1 d . . . . .
C011 C 0.6632(14) 0.2759(7) 0.3383(4) 0.052(2) Uani 1 1 d . . . . .
C012 C -0.5520(13) 0.7835(7) 0.0113(5) 0.055(2) Uani 1 1 d . . . . .
H01M H -0.585873 0.825063 0.045788 0.067 Uiso 1 1 calc R U . . .
H01N H -0.620065 0.783475 -0.032327 0.067 Uiso 1 1 calc R U . . .
C013 C 0.0848(13) 0.8622(7) 0.1470(5) 0.055(2) Uani 1 1 d . . . . .
H01O H 0.133072 0.891557 0.106845 0.066 Uiso 1 1 calc R U . . .
H01P H -0.033710 0.893241 0.153583 0.066 Uiso 1 1 calc R U . . .
C014 C 0.8050(17) 0.2704(8) 0.5032(5) 0.064(3) Uani 1 1 d . . . . .
C015 C 0.6213(17) 0.9352(8) 0.3618(6) 0.073(3) Uani 1 1 d . . . . .
H015 H 0.746513 0.920606 0.357088 0.088 Uiso 1 1 calc R U . . .
C016 C 0.2002(17) 0.3707(9) 0.2522(6) 0.087(4) Uani 1 1 d . . . . .
H016 H 0.191150 0.362628 0.204205 0.104 Uiso 1 1 calc R U . . .
C017 C 0.7960(13) 0.1241(8) 0.1443(5) 0.068(3) Uani 1 1 d . . . . .
H01A H 0.863433 0.184072 0.149761 0.102 Uiso 1 1 calc R U . . .
H01B H 0.805060 0.099084 0.098453 0.102 Uiso 1 1 calc R U . . .
H01C H 0.849197 0.078526 0.178161 0.102 Uiso 1 1 calc R U . . .
C018 C 0.2616(13) 0.4815(7) 0.0424(5) 0.061(3) Uani 1 1 d . . . . .
H01Q H 0.330004 0.465664 0.086306 0.092 Uiso 1 1 calc R U . . .
H01R H 0.309277 0.540727 0.025304 0.092 Uiso 1 1 calc R U . . .
H01S H 0.276381 0.430518 0.009787 0.092 Uiso 1 1 calc R U . . .
C019 C 0.2560(17) 0.9750(8) 0.3773(5) 0.074(3) Uani 1 1 d . . . . .
H019 H 0.130796 0.988787 0.382627 0.089 Uiso 1 1 calc R U . . .
C01A C 1.1395(15) 0.2310(9) 0.5327(5) 0.074(3) Uani 1 1 d . . . . .
H01D H 1.166416 0.253382 0.489403 0.089 Uiso 1 1 calc R U . . .
C01B C 0.572(2) 0.9750(8) 0.4200(5) 0.074(3) Uani 1 1 d . . . . .
C01C C 1.2796(15) 0.1948(9) 0.5779(5) 0.073(3) Uani 1 1 d . . . . .
H01E H 1.402551 0.193982 0.565961 0.088 Uiso 1 1 calc R U . . .
C01D C 0.2802(16) 0.2917(9) 0.3640(5) 0.076(3) Uani 1 1 d . . . . .
H01F H 0.148830 0.278595 0.365757 0.114 Uiso 1 1 calc R U . . .
H01G H 0.311473 0.352460 0.386204 0.114 Uiso 1 1 calc R U . . .
H01H H 0.353498 0.241269 0.387668 0.114 Uiso 1 1 calc R U . . .
C01E C 0.7284(15) 0.3453(8) 0.3941(5) 0.070(3) Uani 1 1 d . . . . .
H01I H 0.781905 0.401292 0.373347 0.084 Uiso 1 1 calc R U . . .
H01J H 0.620732 0.366932 0.416698 0.084 Uiso 1 1 calc R U . . .
C01F C 1.0682(19) 0.1647(10) 0.6582(5) 0.084(4) Uani 1 1 d . . . . .
H01K H 1.043357 0.142548 0.701736 0.101 Uiso 1 1 calc R U . . .
C01G C 0.391(2) 0.9963(9) 0.4299(5) 0.088(4) Uani 1 1 d . . . . .
H01T H 0.360971 1.024279 0.471000 0.105 Uiso 1 1 calc R U . . .
C01H C 0.9255(15) 0.2019(9) 0.6131(5) 0.075(3) Uani 1 1 d . . . . .
H01L H 0.803846 0.204367 0.626256 0.090 Uiso 1 1 calc R U . . .
C1 C 0.113(2) 0.4375(11) 0.2688(9) 0.138(7) Uani 1 1 d . . . . .
H1A H 0.111146 0.452569 0.315582 0.166 Uiso 1 1 calc R U . . .
H1B H 0.044920 0.475056 0.235012 0.166 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
Br01 C00W 1.890(10) . ?
Br02 C01B 1.910(11) . ?
O003 C00A 1.365(10) . ?
O003 C00N 1.454(9) . ?
O004 C00I 1.345(11) . ?
O004 C00L 1.454(10) . ?
O005 C010 1.339(13) . ?
O005 C013 1.448(10) . ?
O006 C014 1.364(11) . ?
O006 C01E 1.448(11) . ?
O007 C00A 1.198(10) . ?
O008 C00I 1.196(11) . ?
C009 C00A 1.482(12) . ?
C009 C00C 1.328(11) . ?
C009 C018 1.492(12) . ?
C00B C00E 1.572(12) . ?
C00B C00F 1.556(12) . ?
C00B C00J 1.538(12) . ?
C00B C00P 1.535(11) . ?
C00C C00N 1.489(12) . ?
C00C C00S 1.511(11) . ?
O00D C014 1.206(12) . ?
C00E H00G 1.0000 . ?
C00E C00M 1.518(11) . ?
C00E C00S 1.549(11) . ?
C00F H00H 0.9900 . ?
C00F H00I 0.9900 . ?
C00F C00N 1.508(11) . ?
O00G C010 1.204(13) . ?
C00H C00K 1.329(12) . ?
C00H C00L 1.499(12) . ?
C00H C00Y 1.492(12) . ?
C00I C00K 1.482(13) . ?
C00J H00J 0.9500 . ?
C00J C012 1.269(12) . ?
C00K C017 1.511(12) . ?
C00L H00L 1.0000 . ?
C00L C00X 1.533(12) . ?
C00M C00T 1.333(11) . ?
C00M C013 1.504(12) . ?
C00N H00N 1.0000 . ?
C00O C00X 1.546(14) . ?
C00O C00Z 1.574(14) . ?
C00O C016 1.523(15) . ?
C00O C01D 1.528(14) . ?
C00P H00K 0.9800 . ?
C00P H00M 0.9800 . ?
C00P H00O 0.9800 . ?
C00Q H00A 0.9500 . ?
C00Q H00B 0.9500 . ?
C00Q C011 1.313(14) . ?
C00R C014 1.470(15) . ?
C00R C01A 1.391(14) . ?
C00R C01H 1.377(13) . ?
C00S H00P 0.9900 . ?
C00S H00Q 0.9900 . ?
C00T H00R 0.9500 . ?
C00T H00S 0.9500 . ?
C00U H00U 0.9500 . ?
C00U C00V 1.384(15) . ?
C00U C015 1.396(14) . ?
C00V C010 1.498(14) . ?
C00V C019 1.389(13) . ?
C00W C01C 1.367(13) . ?
C00W C01F 1.355(15) . ?
C00X H00C 0.9900 . ?
C00X H00D 0.9900 . ?
C00Y H00E 0.9900 . ?
C00Y H00F 0.9900 . ?
C00Y C00Z 1.566(12) . ?
C00Z H00Z 1.0000 . ?
C00Z C011 1.518(13) . ?
C011 C01E 1.514(14) . ?
C012 H01M 0.9500 . ?
C012 H01N 0.9500 . ?
C013 H01O 0.9900 . ?
C013 H01P 0.9900 . ?
C015 H015 0.9500 . ?
C015 C01B 1.361(15) . ?
C016 H016 0.9500 . ?
C016 C1 1.203(17) . ?
C017 H01A 0.9800 . ?
C017 H01B 0.9800 . ?
C017 H01C 0.9800 . ?
C018 H01Q 0.9800 . ?
C018 H01R 0.9800 . ?
C018 H01S 0.9800 . ?
C019 H019 0.9500 . ?
C019 C01G 1.389(15) . ?
C01A H01D 0.9500 . ?
C01A C01C 1.384(14) . ?
C01B C01G 1.384(17) . ?
C01C H01E 0.9500 . ?
C01D H01F 0.9800 . ?
C01D H01G 0.9800 . ?
C01D H01H 0.9800 . ?
C01E H01I 0.9900 . ?
C01E H01J 0.9900 . ?
C01F H01K 0.9500 . ?
C01F C01H 1.400(15) . ?
C01G H01T 0.9500 . ?
C01H H01L 0.9500 . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00A O003 C00N 108.9(6) . . ?
C00I O004 C00L 109.0(7) . . ?
C010 O005 C013 117.6(8) . . ?
C014 O006 C01E 118.3(8) . . ?
C00A C009 C018 120.8(8) . . ?
C00C C009 C00A 107.7(7) . . ?
C00C C009 C018 131.4(8) . . ?
O003 C00A C009 108.7(7) . . ?
O007 C00A O003 120.7(8) . . ?
O007 C00A C009 130.6(9) . . ?
C00F C00B C00E 110.5(6) . . ?
C00J C00B C00E 107.1(7) . . ?
C00J C00B C00F 109.8(7) . . ?
C00P C00B C00E 111.4(7) . . ?
C00P C00B C00F 108.4(7) . . ?
C00P C00B C00J 109.7(7) . . ?
C009 C00C C00N 110.2(7) . . ?
C009 C00C C00S 131.1(8) . . ?
C00N C00C C00S 118.5(7) . . ?
C00B C00E H00G 105.5 . . ?
C00M C00E C00B 114.3(7) . . ?
C00M C00E H00G 105.5 . . ?
C00M C00E C00S 112.8(7) . . ?
C00S C00E C00B 112.3(7) . . ?
C00S C00E H00G 105.5 . . ?
C00B C00F H00H 109.4 . . ?
C00B C00F H00I 109.4 . . ?
H00H C00F H00I 108.0 . . ?
C00N C00F C00B 111.3(7) . . ?
C00N C00F H00H 109.4 . . ?
C00N C00F H00I 109.4 . . ?
C00K C00H C00L 109.1(8) . . ?
C00K C00H C00Y 133.8(9) . . ?
C00Y C00H C00L 117.0(8) . . ?
O004 C00I C00K 109.1(8) . . ?
O008 C00I O004 122.9(9) . . ?
O008 C00I C00K 128.0(10) . . ?
C00B C00J H00J 115.1 . . ?
C012 C00J C00B 129.8(10) . . ?
C012 C00J H00J 115.1 . . ?
C00H C00K C00I 108.0(8) . . ?
C00H C00K C017 129.7(9) . . ?
C00I C00K C017 122.3(8) . . ?
O004 C00L C00H 104.5(7) . . ?
O004 C00L H00L 110.0 . . ?
O004 C00L C00X 112.9(7) . . ?
C00H C00L H00L 110.0 . . ?
C00H C00L C00X 109.3(7) . . ?
C00X C00L H00L 110.0 . . ?
C00T C00M C00E 125.0(8) . . ?
C00T C00M C013 121.7(7) . . ?
C013 C00M C00E 113.3(7) . . ?
O003 C00N C00C 104.3(7) . . ?
O003 C00N C00F 113.0(7) . . ?
O003 C00N H00N 109.4 . . ?
C00C C00N C00F 111.1(7) . . ?
C00C C00N H00N 109.4 . . ?
C00F C00N H00N 109.4 . . ?
C00X C00O C00Z 111.6(8) . . ?
C016 C00O C00X 108.7(8) . . ?
C016 C00O C00Z 108.8(10) . . ?
C016 C00O C01D 109.4(9) . . ?
C01D C00O C00X 106.7(9) . . ?
C01D C00O C00Z 111.6(8) . . ?
C00B C00P H00K 109.5 . . ?
C00B C00P H00M 109.5 . . ?
C00B C00P H00O 109.5 . . ?
H00K C00P H00M 109.5 . . ?
H00K C00P H00O 109.5 . . ?
H00M C00P H00O 109.5 . . ?
H00A C00Q H00B 120.0 . . ?
C011 C00Q H00A 120.0 . . ?
C011 C00Q H00B 120.0 . . ?
C01A C00R C014 122.7(9) . . ?
C01H C00R C014 119.1(10) . . ?
C01H C00R C01A 118.2(10) . . ?
C00C C00S C00E 111.4(7) . . ?
C00C C00S H00P 109.3 . . ?
C00C C00S H00Q 109.3 . . ?
C00E C00S H00P 109.3 . . ?
C00E C00S H00Q 109.3 . . ?
H00P C00S H00Q 108.0 . . ?
C00M C00T H00R 120.0 . . ?
C00M C00T H00S 120.0 . . ?
H00R C00T H00S 120.0 . . ?
C00V C00U H00U 119.7 . . ?
C00V C00U C015 120.7(11) . . ?
C015 C00U H00U 119.7 . . ?
C00U C00V C010 122.2(10) . . ?
C00U C00V C019 119.0(10) . . ?
C019 C00V C010 118.7(10) . . ?
C01C C00W Br01 119.3(9) . . ?
C01F C00W Br01 120.4(8) . . ?
C01F C00W C01C 120.3(10) . . ?
C00L C00X C00O 111.0(8) . . ?
C00L C00X H00C 109.4 . . ?
C00L C00X H00D 109.4 . . ?
C00O C00X H00C 109.4 . . ?
C00O C00X H00D 109.4 . . ?
H00C C00X H00D 108.0 . . ?
C00H C00Y H00E 109.3 . . ?
C00H C00Y H00F 109.3 . . ?
C00H C00Y C00Z 111.5(7) . . ?
H00E C00Y H00F 108.0 . . ?
C00Z C00Y H00E 109.3 . . ?
C00Z C00Y H00F 109.3 . . ?
C00O C00Z H00Z 105.7 . . ?
C00Y C00Z C00O 112.7(7) . . ?
C00Y C00Z H00Z 105.7 . . ?
C011 C00Z C00O 113.7(8) . . ?
C011 C00Z C00Y 112.6(8) . . ?
C011 C00Z H00Z 105.7 . . ?
O005 C010 C00V 111.4(10) . . ?
O00G C010 O005 124.5(11) . . ?
O00G C010 C00V 124.0(11) . . ?
C00Q C011 C00Z 125.8(8) . . ?
C00Q C011 C01E 122.3(9) . . ?
C01E C011 C00Z 111.7(9) . . ?
C00J C012 H01M 120.0 . . ?
C00J C012 H01N 120.0 . . ?
H01M C012 H01N 120.0 . . ?
O005 C013 C00M 112.2(7) . . ?
O005 C013 H01O 109.2 . . ?
O005 C013 H01P 109.2 . . ?
C00M C013 H01O 109.2 . . ?
C00M C013 H01P 109.2 . . ?
H01O C013 H01P 107.9 . . ?
O006 C014 C00R 111.5(10) . . ?
O00D C014 O006 122.2(10) . . ?
O00D C014 C00R 126.3(10) . . ?
C00U C015 H015 120.8 . . ?
C01B C015 C00U 118.4(12) . . ?
C01B C015 H015 120.8 . . ?
C00O C016 H016 112.4 . . ?
C1 C016 C00O 135.2(13) . . ?
C1 C016 H016 112.4 . . ?
C00K C017 H01A 109.5 . . ?
C00K C017 H01B 109.5 . . ?
C00K C017 H01C 109.5 . . ?
H01A C017 H01B 109.5 . . ?
H01A C017 H01C 109.5 . . ?
H01B C017 H01C 109.5 . . ?
C009 C018 H01Q 109.5 . . ?
C009 C018 H01R 109.5 . . ?
C009 C018 H01S 109.5 . . ?
H01Q C018 H01R 109.5 . . ?
H01Q C018 H01S 109.5 . . ?
H01R C018 H01S 109.5 . . ?
C00V C019 H019 119.4 . . ?
C00V C019 C01G 121.3(12) . . ?
C01G C019 H019 119.4 . . ?
C00R C01A H01D 119.7 . . ?
C01C C01A C00R 120.6(10) . . ?
C01C C01A H01D 119.7 . . ?
C015 C01B Br02 119.1(11) . . ?
C015 C01B C01G 123.1(11) . . ?
C01G C01B Br02 117.8(9) . . ?
C00W C01C C01A 120.2(11) . . ?
C00W C01C H01E 119.9 . . ?
C01A C01C H01E 119.9 . . ?
C00O C01D H01F 109.5 . . ?
C00O C01D H01G 109.5 . . ?
C00O C01D H01H 109.5 . . ?
H01F C01D H01G 109.5 . . ?
H01F C01D H01H 109.5 . . ?
H01G C01D H01H 109.5 . . ?
O006 C01E C011 113.5(9) . . ?
O006 C01E H01I 108.9 . . ?
O006 C01E H01J 108.9 . . ?
C011 C01E H01I 108.9 . . ?
C011 C01E H01J 108.9 . . ?
H01I C01E H01J 107.7 . . ?
C00W C01F H01K 120.0 . . ?
C00W C01F C01H 120.0(10) . . ?
C01H C01F H01K 120.0 . . ?
C019 C01G H01T 121.3 . . ?
C01B C01G C019 117.5(11) . . ?
C01B C01G H01T 121.3 . . ?
C00R C01H C01F 120.7(10) . . ?
C00R C01H H01L 119.6 . . ?
C01F C01H H01L 119.6 . . ?
C016 C1 H1A 120.0 . . ?
C016 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?

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
Br01 C00W C01C C01A 178.7(9) . . . . ?
Br01 C00W C01F C01H -179.3(9) . . . . ?
Br02 C01B C01G C019 -179.4(8) . . . . ?
O004 C00I C00K C00H -4.3(9) . . . . ?
O004 C00I C00K C017 174.6(8) . . . . ?
O004 C00L C00X C00O 173.6(8) . . . . ?
O008 C00I C00K C00H 174.3(9) . . . . ?
O008 C00I C00K C017 -6.8(14) . . . . ?
C009 C00C C00N O003 2.6(9) . . . . ?
C009 C00C C00N C00F 124.7(8) . . . . ?
C009 C00C C00S C00E -128.2(9) . . . . ?
C00A O003 C00N C00C -4.4(8) . . . . ?
C00A O003 C00N C00F -125.1(7) . . . . ?
C00A C009 C00C C00N -0.1(9) . . . . ?
C00A C009 C00C C00S 174.8(8) . . . . ?
C00B C00E C00M C00T 81.4(11) . . . . ?
C00B C00E C00M C013 -100.3(9) . . . . ?
C00B C00E C00S C00C -45.9(9) . . . . ?
C00B C00F C00N O003 171.7(7) . . . . ?
C00B C00F C00N C00C 54.9(8) . . . . ?
C00C C009 C00A O003 -2.8(9) . . . . ?
C00C C009 C00A O007 178.2(9) . . . . ?
C00E C00B C00F C00N -57.3(8) . . . . ?
C00E C00B C00J C012 -119.2(11) . . . . ?
C00E C00M C013 O005 179.2(7) . . . . ?
C00F C00B C00E C00M -77.4(9) . . . . ?
C00F C00B C00E C00S 52.7(9) . . . . ?
C00F C00B C00J C012 120.8(11) . . . . ?
C00H C00L C00X C00O 57.7(10) . . . . ?
C00H C00Y C00Z C00O -44.8(10) . . . . ?
C00H C00Y C00Z C011 85.4(10) . . . . ?
C00I O004 C00L C00H -1.9(9) . . . . ?
C00I O004 C00L C00X -120.6(8) . . . . ?
C00J C00B C00E C00M 163.1(7) . . . . ?
C00J C00B C00E C00S -66.8(9) . . . . ?
C00J C00B C00F C00N 60.6(9) . . . . ?
C00K C00H C00L O004 -0.8(9) . . . . ?
C00K C00H C00L C00X 120.3(8) . . . . ?
C00K C00H C00Y C00Z -125.9(10) . . . . ?
C00L O004 C00I O008 -174.9(8) . . . . ?
C00L O004 C00I C00K 3.7(9) . . . . ?
C00L C00H C00K C00I 2.9(9) . . . . ?
C00L C00H C00K C017 -175.8(9) . . . . ?
C00L C00H C00Y C00Z 50.3(10) . . . . ?
C00M C00E C00S C00C 85.0(9) . . . . ?
C00N O003 C00A O007 -176.4(8) . . . . ?
C00N O003 C00A C009 4.5(8) . . . . ?
C00N C00C C00S C00E 46.3(10) . . . . ?
C00O C00Z C011 C00Q 83.6(12) . . . . ?
C00O C00Z C011 C01E -102.2(10) . . . . ?
C00P C00B C00E C00M 43.1(9) . . . . ?
C00P C00B C00E C00S 173.3(7) . . . . ?
C00P C00B C00F C00N -179.6(7) . . . . ?
C00P C00B C00J C012 1.8(14) . . . . ?
C00Q C011 C01E O006 -2.2(15) . . . . ?
C00R C01A C01C C00W 1.6(19) . . . . ?
C00S C00C C00N O003 -173.0(7) . . . . ?
C00S C00C C00N C00F -50.9(10) . . . . ?
C00S C00E C00M C00T -48.5(11) . . . . ?
C00S C00E C00M C013 129.8(8) . . . . ?
C00T C00M C013 O005 -2.5(13) . . . . ?
C00U C00V C010 O005 3.1(14) . . . . ?
C00U C00V C010 O00G -176.0(11) . . . . ?
C00U C00V C019 C01G -1.4(17) . . . . ?
C00U C015 C01B Br02 -179.4(8) . . . . ?
C00U C015 C01B C01G 1.1(17) . . . . ?
C00V C00U C015 C01B -2.5(16) . . . . ?
C00V C019 C01G C01B 0.0(17) . . . . ?
C00W C01F C01H C00R -0.4(19) . . . . ?
C00X C00O C00Z C00Y 48.8(10) . . . . ?
C00X C00O C00Z C011 -80.8(10) . . . . ?
C00X C00O C016 C1 135(2) . . . . ?
C00Y C00H C00K C00I 179.4(9) . . . . ?
C00Y C00H C00K C017 0.6(16) . . . . ?
C00Y C00H C00L O004 -177.9(7) . . . . ?
C00Y C00H C00L C00X -56.8(10) . . . . ?
C00Y C00Z C011 C00Q -46.0(14) . . . . ?
C00Y C00Z C011 C01E 128.1(9) . . . . ?
C00Z C00O C00X C00L -55.6(10) . . . . ?
C00Z C00O C016 C1 -103(2) . . . . ?
C00Z C011 C01E O006 -176.6(8) . . . . ?
C010 O005 C013 C00M -111.4(10) . . . . ?
C010 C00V C019 C01G -177.5(10) . . . . ?
C013 O005 C010 O00G 2.3(16) . . . . ?
C013 O005 C010 C00V -176.8(7) . . . . ?
C014 O006 C01E C011 -95.8(11) . . . . ?
C014 C00R C01A C01C -178.4(11) . . . . ?
C014 C00R C01H C01F 177.9(11) . . . . ?
C015 C00U C00V C010 178.6(10) . . . . ?
C015 C00U C00V C019 2.7(16) . . . . ?
C015 C01B C01G C019 0.2(18) . . . . ?
C016 C00O C00X C00L 64.4(11) . . . . ?
C016 C00O C00Z C00Y -71.1(10) . . . . ?
C016 C00O C00Z C011 159.3(8) . . . . ?
C018 C009 C00A O003 174.8(7) . . . . ?
C018 C009 C00A O007 -4.2(14) . . . . ?
C018 C009 C00C C00N -177.3(9) . . . . ?
C018 C009 C00C C00S -2.5(16) . . . . ?
C019 C00V C010 O005 179.1(9) . . . . ?
C019 C00V C010 O00G -0.1(17) . . . . ?
C01A C00R C014 O006 -5.7(16) . . . . ?
C01A C00R C014 O00D 173.2(12) . . . . ?
C01A C00R C01H C01F -0.6(17) . . . . ?
C01C C00W C01F C01H 2.1(18) . . . . ?
C01D C00O C00X C00L -177.7(8) . . . . ?
C01D C00O C00Z C00Y 168.1(8) . . . . ?
C01D C00O C00Z C011 38.5(12) . . . . ?
C01D C00O C016 C1 19(3) . . . . ?
C01E O006 C014 O00D 2.0(16) . . . . ?
C01E O006 C014 C00R -179.1(9) . . . . ?
C01F C00W C01C C01A -2.6(18) . . . . ?
C01H C00R C014 O006 175.8(9) . . . . ?
C01H C00R C014 O00D -5.3(18) . . . . ?
C01H C00R C01A C01C 0.1(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.482
_oxdiff_exptl_absorpt_empirical_full_min 0.478
####################################################################### 
# 
# 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_kpk_227_as_112_0m
_database_code_depnum_ccdc_archive 'CCDC 2482392'
loop_
_audit_author_name
_audit_author_address
'Anisha Suresh'
;PhD Scholar
India
;
_audit_update_record             
;
2025-08-23 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2025-03-24
_audit_creation_method           
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
darshansmhatre@chem.iitb.ac.in
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H23 Br O4'
_chemical_formula_sum            'C22 H23 Br O4'
_chemical_formula_weight         431.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.3798(15)
_cell_length_b                   10.7769(19)
_cell_length_c                   19.553(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1976.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3581
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      22.26
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.632
_shelx_estimated_absorpt_T_min   0.472
_exptl_absorpt_coefficient_mu    2.104
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4424
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1414 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.5933.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14108
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.083
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.738
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2789
_reflns_number_total             3477
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.094(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.4216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1068
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C13(H13), C14(H14), C20(H20)
2.d X=CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
2.e Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.34968(9) 0.28098(7) 0.48455(4) 0.0696(3) Uani 1 1 d . . . . .
O1 O 0.8440(4) 0.6165(4) 0.6484(2) 0.0475(10) Uani 1 1 d . . . . .
O2 O 0.0514(4) 0.8330(5) 0.7375(2) 0.0561(12) Uani 1 1 d . . . . .
O3 O -0.0398(6) 0.9954(5) 0.6813(3) 0.0895(18) Uani 1 1 d . . . . .
C21 C 0.5705(9) 0.5958(9) 0.8460(4) 0.091(3) Uani 1 1 d . . . . .
H21A H 0.541886 0.511261 0.845993 0.109 Uiso 1 1 calc R U . . .
H21B H 0.642178 0.623369 0.876801 0.109 Uiso 1 1 calc R U . . .
C22 C 0.5765(6) 0.5233(6) 0.6189(3) 0.0436(15) Uani 1 1 d . . . . .
H22A H 0.660997 0.484666 0.602612 0.052 Uiso 1 1 calc R U . . .
H22B H 0.486139 0.487680 0.609166 0.052 Uiso 1 1 calc R U . . .
O6 O 0.8581(5) 0.7340(4) 0.5541(2) 0.0562(11) Uani 1 1 d . . . . .
C1 C 1.2129(6) 0.3941(5) 0.5188(3) 0.0436(14) Uani 1 1 d . . . . .
C2 C 1.1885(6) 0.5016(5) 0.4824(3) 0.0440(14) Uani 1 1 d . . . . .
H2 H 1.241211 0.519250 0.442092 0.053 Uiso 1 1 calc R U . . .
C3 C 1.0856(6) 0.5834(5) 0.5059(3) 0.0432(14) Uani 1 1 d . . . . .
H3 H 1.066622 0.657570 0.481287 0.052 Uiso 1 1 calc R U . . .
C4 C 1.0102(5) 0.5575(5) 0.5650(3) 0.0335(12) Uani 1 1 d . . . . .
C5 C 0.8982(6) 0.6465(6) 0.5875(3) 0.0398(13) Uani 1 1 d . . . . .
C6 C 0.7250(6) 0.6876(6) 0.6724(3) 0.0481(17) Uani 1 1 d . . . . .
H6A H 0.727948 0.771195 0.651433 0.058 Uiso 1 1 calc R U . . .
H6B H 0.732226 0.697746 0.722588 0.058 Uiso 1 1 calc R U . . .
C7 C 0.5848(5) 0.6263(5) 0.6551(3) 0.0349(13) Uani 1 1 d . . . . .
C8 C 0.4549(5) 0.6967(5) 0.6807(2) 0.0307(12) Uani 1 1 d . . . . .
H8 H 0.485825 0.784808 0.686708 0.037 Uiso 1 1 calc R U . . .
C9 C 0.3340(5) 0.6985(5) 0.6272(2) 0.0314(12) Uani 1 1 d . . . . .
H9A H 0.369074 0.736707 0.584305 0.038 Uiso 1 1 calc R U . . .
H9B H 0.303882 0.612495 0.616852 0.038 Uiso 1 1 calc R U . . .
C10 C 0.2097(5) 0.7708(6) 0.6537(3) 0.0345(12) Uani 1 1 d . . . . .
C11 C 0.1409(6) 0.8688(5) 0.6294(3) 0.0421(13) Uani 1 1 d . . . . .
C12 C 0.1510(7) 0.9351(6) 0.5630(3) 0.0556(16) Uani 1 1 d . . . . .
H12A H 0.246619 0.923835 0.543798 0.083 Uiso 1 1 calc R U . . .
H12B H 0.132888 1.023682 0.570137 0.083 Uiso 1 1 calc R U . . .
H12C H 0.080011 0.901429 0.531211 0.083 Uiso 1 1 calc R U . . .
C13 C 1.1416(6) 0.3687(5) 0.5779(3) 0.0442(14) Uani 1 1 d . . . . .
H13 H 1.161940 0.295035 0.602739 0.053 Uiso 1 1 calc R U . . .
C14 C 1.0390(6) 0.4510(5) 0.6015(3) 0.0393(13) Uani 1 1 d . . . . .
H14 H 0.988865 0.434011 0.642703 0.047 Uiso 1 1 calc R U . . .
C15 C 0.1553(6) 0.7388(5) 0.7231(3) 0.0400(13) Uani 1 1 d . . . . .
H15 H 0.108045 0.655589 0.721924 0.048 Uiso 1 1 calc R U . . .
C16 C 0.0423(7) 0.9089(6) 0.6826(4) 0.0536(17) Uani 1 1 d . . . . .
C17 C 0.2758(6) 0.7378(6) 0.7750(3) 0.0420(14) Uani 1 1 d . . . . .
H17A H 0.238750 0.708630 0.819589 0.050 Uiso 1 1 calc R U . . .
H17B H 0.311857 0.823366 0.781169 0.050 Uiso 1 1 calc R U . . .
C18 C 0.4001(5) 0.6526(5) 0.7522(3) 0.0366(13) Uani 1 1 d . . . . .
C19 C 0.3526(7) 0.5171(5) 0.7500(3) 0.0491(14) Uani 1 1 d . . . . .
H19A H 0.435452 0.463779 0.741650 0.074 Uiso 1 1 calc R U . . .
H19B H 0.282890 0.505762 0.713238 0.074 Uiso 1 1 calc R U . . .
H19C H 0.308994 0.494666 0.793890 0.074 Uiso 1 1 calc R U . . .
C20 C 0.5140(7) 0.6708(7) 0.8055(3) 0.0530(17) Uani 1 1 d . . . . .
H20 H 0.548903 0.753299 0.808877 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.892(6) . ?
O1 C5 1.336(7) . ?
O1 C6 1.433(6) . ?
O2 C15 1.435(6) . ?
O2 C16 1.352(8) . ?
O3 C16 1.210(7) . ?
C21 H21A 0.9500 . ?
C21 H21B 0.9500 . ?
C21 C20 1.250(10) . ?
C22 H22A 0.9500 . ?
C22 H22B 0.9500 . ?
C22 C7 1.318(8) . ?
O6 C5 1.206(6) . ?
C1 C2 1.379(8) . ?
C1 C13 1.362(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(8) . ?
C4 C5 1.489(8) . ?
C4 C14 1.379(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.510(7) . ?
C7 C8 1.520(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.544(7) . ?
C8 C18 1.562(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.495(7) . ?
C10 C11 1.325(8) . ?
C10 C15 1.490(8) . ?
C11 C12 1.485(8) . ?
C11 C16 1.457(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C14 1.388(8) . ?
C14 H14 0.9500 . ?
C15 H15 1.0000 . ?
C15 C17 1.519(8) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.550(8) . ?
C18 C19 1.528(8) . ?
C18 C20 1.505(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C6 117.3(5) . . ?
C16 O2 C15 108.3(4) . . ?
H21A C21 H21B 120.0 . . ?
C20 C21 H21A 120.0 . . ?
C20 C21 H21B 120.0 . . ?
H22A C22 H22B 120.0 . . ?
C7 C22 H22A 120.0 . . ?
C7 C22 H22B 120.0 . . ?
C2 C1 Br1 118.1(5) . . ?
C13 C1 Br1 120.2(4) . . ?
C13 C1 C2 121.7(5) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(6) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 118.5(5) . . ?
C14 C4 C3 120.0(5) . . ?
C14 C4 C5 121.5(5) . . ?
O1 C5 C4 112.0(5) . . ?
O6 C5 O1 123.6(5) . . ?
O6 C5 C4 124.3(5) . . ?
O1 C6 H6A 109.3 . . ?
O1 C6 H6B 109.3 . . ?
O1 C6 C7 111.8(5) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C22 C7 C6 122.7(5) . . ?
C22 C7 C8 123.4(5) . . ?
C6 C7 C8 113.9(4) . . ?
C7 C8 H8 106.3 . . ?
C7 C8 C9 111.8(4) . . ?
C7 C8 C18 114.0(4) . . ?
C9 C8 H8 106.3 . . ?
C9 C8 C18 111.7(4) . . ?
C18 C8 H8 106.3 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C10 C9 C8 110.1(4) . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C11 C10 C9 132.1(5) . . ?
C11 C10 C15 110.1(5) . . ?
C15 C10 C9 117.5(5) . . ?
C10 C11 C12 131.8(6) . . ?
C10 C11 C16 106.8(5) . . ?
C16 C11 C12 121.4(6) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 C13 H13 120.2 . . ?
C1 C13 C14 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C4 C14 C13 119.7(5) . . ?
C4 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O2 C15 C10 104.3(4) . . ?
O2 C15 H15 109.8 . . ?
O2 C15 C17 112.3(4) . . ?
C10 C15 H15 109.8 . . ?
C10 C15 C17 110.8(4) . . ?
C17 C15 H15 109.8 . . ?
O2 C16 C11 110.3(5) . . ?
O3 C16 O2 121.5(6) . . ?
O3 C16 C11 128.2(7) . . ?
C15 C17 H17A 109.2 . . ?
C15 C17 H17B 109.2 . . ?
C15 C17 C18 111.8(4) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 C8 108.9(4) . . ?
C19 C18 C8 111.2(5) . . ?
C19 C18 C17 110.8(5) . . ?
C20 C18 C8 110.2(4) . . ?
C20 C18 C17 105.0(5) . . ?
C20 C18 C19 110.5(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C18 131.0(7) . . ?
C21 C20 H20 114.5 . . ?
C18 C20 H20 114.5 . . ?

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
Br1 C1 C2 C3 178.1(4) . . . . ?
Br1 C1 C13 C14 -178.4(4) . . . . ?
O1 C6 C7 C22 -3.5(9) . . . . ?
O1 C6 C7 C8 178.8(4) . . . . ?
O2 C15 C17 C18 -169.8(4) . . . . ?
C22 C7 C8 C9 -39.3(7) . . . . ?
C22 C7 C8 C18 88.5(7) . . . . ?
C1 C2 C3 C4 0.6(8) . . . . ?
C1 C13 C14 C4 0.1(8) . . . . ?
C2 C1 C13 C14 1.6(9) . . . . ?
C2 C3 C4 C5 -178.5(5) . . . . ?
C2 C3 C4 C14 1.1(8) . . . . ?
C3 C4 C5 O1 -173.9(5) . . . . ?
C3 C4 C5 O6 7.7(8) . . . . ?
C3 C4 C14 C13 -1.4(8) . . . . ?
C5 O1 C6 C7 94.7(6) . . . . ?
C5 C4 C14 C13 178.2(5) . . . . ?
C6 O1 C5 O6 4.8(8) . . . . ?
C6 O1 C5 C4 -173.7(4) . . . . ?
C6 C7 C8 C9 138.5(5) . . . . ?
C6 C7 C8 C18 -93.7(6) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C7 C8 C18 C17 175.6(4) . . . . ?
C7 C8 C18 C19 -62.0(6) . . . . ?
C7 C8 C18 C20 60.9(6) . . . . ?
C8 C9 C10 C11 123.1(6) . . . . ?
C8 C9 C10 C15 -50.6(6) . . . . ?
C8 C18 C20 C21 -124.1(9) . . . . ?
C9 C8 C18 C17 -56.5(5) . . . . ?
C9 C8 C18 C19 65.9(6) . . . . ?
C9 C8 C18 C20 -171.2(5) . . . . ?
C9 C10 C11 C12 7.9(11) . . . . ?
C9 C10 C11 C16 -171.8(6) . . . . ?
C9 C10 C15 O2 172.5(4) . . . . ?
C9 C10 C15 C17 51.5(7) . . . . ?
C10 C11 C16 O2 -1.2(7) . . . . ?
C10 C11 C16 O3 179.6(7) . . . . ?
C10 C15 C17 C18 -53.6(6) . . . . ?
C11 C10 C15 O2 -2.6(6) . . . . ?
C11 C10 C15 C17 -123.6(5) . . . . ?
C12 C11 C16 O2 179.1(6) . . . . ?
C12 C11 C16 O3 -0.2(11) . . . . ?
C13 C1 C2 C3 -1.9(9) . . . . ?
C14 C4 C5 O1 6.5(7) . . . . ?
C14 C4 C5 O6 -172.0(5) . . . . ?
C15 O2 C16 O3 178.8(6) . . . . ?
C15 O2 C16 C11 -0.5(7) . . . . ?
C15 C10 C11 C12 -178.0(6) . . . . ?
C15 C10 C11 C16 2.3(6) . . . . ?
C15 C17 C18 C8 57.2(6) . . . . ?
C15 C17 C18 C19 -65.5(6) . . . . ?
C15 C17 C18 C20 175.3(5) . . . . ?
C16 O2 C15 C10 1.8(6) . . . . ?
C16 O2 C15 C17 121.8(5) . . . . ?
C17 C18 C20 C21 118.7(9) . . . . ?
C18 C8 C9 C10 52.2(6) . . . . ?
C19 C18 C20 C21 -0.7(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kpk_170_as_169_autored
_database_code_depnum_ccdc_archive 'CCDC 2504653'
loop_
_audit_author_name
_audit_author_address
'Darshan Mhatre'
;PhD research scholar 
India
;
_audit_update_record             
;
2025-11-21 deposited with the CCDC.	2026-01-29 downloaded from the CCDC.
;
_audit_creation_date             2022-02-14
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O3'
_chemical_formula_sum            'C14 H20 O3'
_chemical_formula_weight         236.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.8535(2)
_cell_length_b                   8.0124(2)
_cell_length_c                   9.0131(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.910(3)
_cell_angle_gamma                90
_cell_volume                     617.84(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5434
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.5850
_cell_measurement_theta_min      2.3250
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.899
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            16706
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.462
_diffrn_reflns_theta_min         2.338
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.899
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -169.73  14.27   1.00    2.00   9.41 -12.98 -31.50    --   184
  2  φ     24.08 208.08   1.00    2.00  16.12 -12.98 -59.25    --   184
  3  ω   -108.63  15.37   1.00    2.00    --  -12.98 -59.25  71.08  124
  4  ω   -108.63  15.37   1.00    2.00    --  -12.98 -59.25 -33.92  124
  5  ω   -108.63  15.37   1.00    2.00    --  -12.98 -59.25  20.08  124
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648308000
_diffrn_orient_matrix_UB_12      0.0017394000
_diffrn_orient_matrix_UB_13      0.0326194000
_diffrn_orient_matrix_UB_21      -0.0394451000
_diffrn_orient_matrix_UB_22      0.0554491000
_diffrn_orient_matrix_UB_23      -0.0585289000
_diffrn_orient_matrix_UB_31      -0.0333621000
_diffrn_orient_matrix_UB_32      -0.0689971000
_diffrn_orient_matrix_UB_33      -0.0462975000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.777
_reflns_number_gt                3307
_reflns_number_total             4063
_reflns_odcompleteness_completeness 89.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.39
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1255 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         4063
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.0015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.10233(13) 0.28167(17) 0.22924(14) 0.0242(3) Uani 1 1 d . . . . .
O2 O 0.18352(13) 0.42856(15) 0.04541(14) 0.0229(3) Uani 1 1 d . . . . .
O3 O 0.85855(16) 0.47114(16) 0.61216(15) 0.0295(3) Uani 1 1 d . . . . .
H3 H 0.870195 0.568697 0.647377 0.044 Uiso 1 1 calc GR . . . .
C1 C 0.22994(19) 0.3801(2) 0.2032(2) 0.0191(3) Uani 1 1 d . . . . .
C2 C -0.02500(19) 0.2931(2) 0.0941(2) 0.0264(4) Uani 1 1 d . . . . .
H2A H -0.094414 0.388226 0.100403 0.032 Uiso 1 1 calc R . . . .
H2B H -0.087258 0.188953 0.076780 0.032 Uiso 1 1 calc R . . . .
C3 C 0.0588(2) 0.3200(2) -0.0299(2) 0.0276(4) Uani 1 1 d . . . . .
H3A H 0.099067 0.213639 -0.060551 0.033 Uiso 1 1 calc R . . . .
H3B H -0.010130 0.373682 -0.121519 0.033 Uiso 1 1 calc R . . . .
C4 C 0.25152(19) 0.5352(2) 0.3033(2) 0.0210(3) Uani 1 1 d . . . . .
H4A H 0.256037 0.502170 0.410163 0.025 Uiso 1 1 calc R . . . .
H4B H 0.159926 0.609232 0.266971 0.025 Uiso 1 1 calc R . . . .
C5 C 0.37562(18) 0.27029(19) 0.23737(18) 0.0179(3) Uani 1 1 d . . . . .
H5A H 0.360410 0.180781 0.159191 0.021 Uiso 1 1 calc R . . . .
H5B H 0.387481 0.216449 0.338585 0.021 Uiso 1 1 calc R . . . .
C6 C 0.52786(18) 0.36511(18) 0.23883(19) 0.0157(3) Uani 1 1 d . . . . .
C7 C 0.54138(18) 0.51606(18) 0.35044(18) 0.0158(3) Uani 1 1 d . . . . .
H7 H 0.537451 0.468399 0.451924 0.019 Uiso 1 1 calc R . . . .
C8 C 0.40032(19) 0.6318(2) 0.3013(2) 0.0196(3) Uani 1 1 d . . . . .
H8A H 0.392638 0.674949 0.196659 0.024 Uiso 1 1 calc R . . . .
H8B H 0.412744 0.728066 0.372311 0.024 Uiso 1 1 calc R . . . .
C9 C 0.66606(19) 0.2513(2) 0.2997(2) 0.0198(3) Uani 1 1 d . . . . .
H9 H 0.655779 0.137268 0.269943 0.024 Uiso 1 1 calc R . . . .
C10 C 0.80055(19) 0.3004(2) 0.39181(19) 0.0213(3) Uani 1 1 d . . . . .
H10 H 0.880879 0.219646 0.424135 0.026 Uiso 1 1 calc R . . . .
C11 C 0.83332(19) 0.4763(2) 0.4481(2) 0.0217(4) Uani 1 1 d . . . . .
H11 H 0.931311 0.515508 0.423428 0.026 Uiso 1 1 calc R . . . .
C12 C 0.70128(19) 0.5935(2) 0.37424(19) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.5314(2) 0.4198(2) 0.0757(2) 0.0211(3) Uani 1 1 d . . . . .
H13A H 0.529515 0.320880 0.011357 0.032 Uiso 1 1 calc GR . . . .
H13B H 0.626914 0.483777 0.080792 0.032 Uiso 1 1 calc GR . . . .
H13C H 0.439949 0.489515 0.031436 0.032 Uiso 1 1 calc GR . . . .
C14 C 0.7290(2) 0.7481(2) 0.3356(2) 0.0268(4) Uani 1 1 d . . . . .
H14A H 0.644347 0.819476 0.288926 0.032 Uiso 1 1 calc R . . . .
H14B H 0.833406 0.787525 0.354508 0.032 Uiso 1 1 calc R . . . .


_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 C1 1.4459(19) . ?
O1 C2 1.434(2) . ?
O2 C1 1.429(2) . ?
O2 C3 1.433(2) . ?
O3 C11 1.438(2) . ?
C1 C4 1.518(2) . ?
C1 C5 1.526(2) . ?
C2 C3 1.507(3) . ?
C4 C8 1.532(2) . ?
C5 C6 1.544(2) . ?
C6 C7 1.558(2) . ?
C6 C9 1.511(2) . ?
C6 C13 1.542(2) . ?
C7 C8 1.527(2) . ?
C7 C12 1.510(2) . ?
C9 C10 1.324(2) . ?
C10 C11 1.501(3) . ?
C11 C12 1.514(2) . ?
C12 C14 1.327(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 O1 C1 107.67(13) . . ?
C1 O2 C3 107.21(13) . . ?
O1 C1 C4 109.53(14) . . ?
O1 C1 C5 107.92(12) . . ?
O2 C1 O1 105.85(13) . . ?
O2 C1 C4 109.22(13) . . ?
O2 C1 C5 111.67(13) . . ?
C4 C1 C5 112.42(13) . . ?
O1 C2 C3 102.11(13) . . ?
O2 C3 C2 101.66(14) . . ?
C1 C4 C8 112.57(13) . . ?
C1 C5 C6 114.11(12) . . ?
C5 C6 C7 108.02(12) . . ?
C9 C6 C5 109.24(12) . . ?
C9 C6 C7 108.27(12) . . ?
C9 C6 C13 107.72(13) . . ?
C13 C6 C5 111.31(13) . . ?
C13 C6 C7 112.20(12) . . ?
C8 C7 C6 111.29(12) . . ?
C12 C7 C6 108.93(13) . . ?
C12 C7 C8 117.28(13) . . ?
C7 C8 C4 109.33(13) . . ?
C10 C9 C6 124.18(15) . . ?
C9 C10 C11 123.73(15) . . ?
O3 C11 C10 106.61(13) . . ?
O3 C11 C12 111.59(14) . . ?
C10 C11 C12 111.96(14) . . ?
C7 C12 C11 113.40(13) . . ?
C14 C12 C7 125.21(16) . . ?
C14 C12 C11 121.40(16) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.858
