# 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_dbr011_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2360360'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-06-04 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-05-10
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H27 N O6'
_chemical_formula_sum            'C23 H27 N O6'
_chemical_formula_weight         413.45
_chemical_absolute_configuration syn
_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'
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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8373(7)
_cell_length_b                   12.5432(11)
_cell_length_c                   18.3743(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2267.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5048
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1325 before and 0.0636 after correction.
The Ratio of minimum to maximum transmission is 0.8478.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic yellowish yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7149
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         1.966
_diffrn_ambient_temperature      296.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.980
_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_standards_number         0
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.901
_reflns_number_gt                4170
_reflns_number_total             4922
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details 
;
 Flack x determined using 1489 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0780
_refine_ls_restrained_S_all      1.191
_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)+(0.1027P)²+0.1288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1758
_refine_ls_wR_factor_ref         0.1819
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C11(H11), C4(H4), C1(H1)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O6 O 0.4281(2) 0.8637(2) 0.30924(14) 0.0576(6) Uani 1 1 d . . . . .
O3 O 0.6685(2) 0.77257(18) 0.37236(11) 0.0485(5) Uani 1 1 d . . . . .
O4 O 0.7273(3) 0.9194(2) 0.30993(15) 0.0686(7) Uani 1 1 d . . . . .
O2 O 0.4001(3) 0.6656(2) 0.40762(16) 0.0735(8) Uani 1 1 d . . . . .
O1 O 0.5500(4) 0.5572(3) 0.44863(17) 0.0889(10) Uani 1 1 d . . . . .
N1 N 0.5002(3) 0.6100(2) 0.40022(16) 0.0558(7) Uani 1 1 d . . . . .
C13 C 0.4689(3) 0.7791(3) 0.28979(16) 0.0467(7) Uani 1 1 d . . . . .
O5 O 0.4328(3) 0.7270(4) 0.10812(15) 0.1009(13) Uani 1 1 d . . . . .
C6 C 0.1652(3) 0.6927(3) 0.2872(2) 0.0570(8) Uani 1 1 d . . . . .
C22 C 0.7169(3) 0.8745(3) 0.36628(18) 0.0495(7) Uani 1 1 d . . . . .
C2 C 0.0544(4) 0.7503(3) 0.3976(3) 0.0726(11) Uani 1 1 d . . . . .
H2 H 0.034865 0.805390 0.429853 0.087 Uiso 1 1 calc R . . . .
C12 C 0.6053(3) 0.7278(3) 0.30946(16) 0.0470(7) Uani 1 1 d . . . . .
C5 C 0.1126(3) 0.5916(3) 0.3002(2) 0.0648(10) Uani 1 1 d . . . . .
H5 H 0.129935 0.536918 0.267338 0.078 Uiso 1 1 calc R . . . .
C11 C 0.6912(3) 0.7307(3) 0.24177(18) 0.0541(8) Uani 1 1 d . . . . .
H11 H 0.784874 0.736551 0.247233 0.065 Uiso 1 1 calc R . . . .
C7 C 0.2545(3) 0.7133(4) 0.2221(2) 0.0639(9) Uani 1 1 d . . . . .
H7A H 0.238140 0.785323 0.205086 0.077 Uiso 1 1 calc R . . . .
H7B H 0.228347 0.664871 0.183444 0.077 Uiso 1 1 calc R . . . .
C4 C 0.0351(3) 0.5713(3) 0.3612(2) 0.0660(10) Uani 1 1 d . . . . .
H4 H 0.002497 0.502631 0.368957 0.079 Uiso 1 1 calc R . . . .
C15 C 0.5660(3) 0.6105(3) 0.32453(18) 0.0501(7) Uani 1 1 d . . . . .
C10 C 0.6410(3) 0.7253(3) 0.17415(18) 0.0592(8) Uani 1 1 d . . . . .
C8 C 0.4081(3) 0.7000(3) 0.23667(18) 0.0530(8) Uani 1 1 d . . . . .
C16 C 0.6812(4) 0.5301(3) 0.3239(2) 0.0675(10) Uani 1 1 d . . . . .
H16A H 0.751065 0.552688 0.356967 0.101 Uiso 1 1 calc GR . . . .
H16B H 0.718168 0.525114 0.275636 0.101 Uiso 1 1 calc GR . . . .
H16C H 0.647397 0.461651 0.338618 0.101 Uiso 1 1 calc GR . . . .
C3 C 0.0045(3) 0.6500(4) 0.4112(2) 0.0649(9) Uani 1 1 d . . . . .
C23 C 0.7527(4) 0.9191(4) 0.4389(2) 0.0696(10) Uani 1 1 d . . . . .
H23A H 0.675918 0.956593 0.458496 0.104 Uiso 1 1 calc GR . . . .
H23B H 0.827926 0.967288 0.433943 0.104 Uiso 1 1 calc GR . . . .
H23C H 0.777402 0.862031 0.471155 0.104 Uiso 1 1 calc GR . . . .
C14 C 0.4526(3) 0.5906(3) 0.2677(2) 0.0549(8) Uani 1 1 d . . . . .
H14A H 0.375922 0.555174 0.290446 0.066 Uiso 1 1 calc R . . . .
H14B H 0.486418 0.545367 0.228867 0.066 Uiso 1 1 calc R . . . .
C1 C 0.1327(4) 0.7709(4) 0.3372(3) 0.0708(10) Uani 1 1 d . . . . .
H1 H 0.164805 0.839758 0.329712 0.085 Uiso 1 1 calc R . . . .
C9 C 0.4909(4) 0.7190(4) 0.1655(2) 0.0644(9) Uani 1 1 d . . . . .
C17 C 0.7322(4) 0.7277(4) 0.1061(2) 0.0755(12) Uani 1 1 d . . . . .
C20 C 0.7016(7) 0.6298(6) 0.0595(3) 0.116(2) Uani 1 1 d . . . . .
H20A H 0.717913 0.566394 0.087429 0.174 Uiso 1 1 calc GR . . . .
H20B H 0.759499 0.629943 0.017417 0.174 Uiso 1 1 calc GR . . . .
H20C H 0.608280 0.631502 0.044317 0.174 Uiso 1 1 calc GR . . . .
C21 C -0.0809(5) 0.6278(5) 0.4775(3) 0.0836(12) Uani 1 1 d . . . . .
H21A H -0.040683 0.661539 0.519138 0.125 Uiso 1 1 calc GR . . . .
H21B H -0.085623 0.552257 0.485448 0.125 Uiso 1 1 calc GR . . . .
H21C H -0.170863 0.655437 0.470104 0.125 Uiso 1 1 calc GR . . . .
C19 C 0.8826(5) 0.7279(7) 0.1272(3) 0.110(2) Uani 1 1 d . . . . .
H19A H 0.898768 0.782806 0.162543 0.166 Uiso 1 1 calc GR . . . .
H19B H 0.936976 0.741028 0.084777 0.166 Uiso 1 1 calc GR . . . .
H19C H 0.906382 0.659905 0.147580 0.166 Uiso 1 1 calc GR . . . .
C18 C 0.7025(7) 0.8289(5) 0.0625(3) 0.1071(18) Uani 1 1 d . . . . .
H18A H 0.608490 0.829690 0.048413 0.161 Uiso 1 1 calc GR . . . .
H18B H 0.758559 0.830238 0.019709 0.161 Uiso 1 1 calc GR . . . .
H18C H 0.721748 0.890325 0.091878 0.161 Uiso 1 1 calc GR . . . .


_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
O6 C13 1.190(4) . ?
O3 C22 1.369(4) . ?
O3 C12 1.428(4) . ?
O4 C22 1.183(4) . ?
O2 N1 1.214(4) . ?
O1 N1 1.213(4) . ?
N1 C15 1.534(4) . ?
C13 C12 1.531(4) . ?
C13 C8 1.515(5) . ?
O5 C9 1.203(5) . ?
C6 C5 1.390(5) . ?
C6 C7 1.505(5) . ?
C6 C1 1.381(6) . ?
C22 C23 1.489(5) . ?
C2 C3 1.373(6) . ?
C2 C1 1.376(6) . ?
C12 C11 1.504(4) . ?
C12 C15 1.546(5) . ?
C5 C4 1.380(6) . ?
C11 C10 1.339(5) . ?
C7 C8 1.543(4) . ?
C4 C3 1.382(6) . ?
C15 C16 1.518(5) . ?
C15 C14 1.548(4) . ?
C10 C9 1.488(5) . ?
C10 C17 1.539(5) . ?
C8 C14 1.550(5) . ?
C8 C9 1.560(5) . ?
C3 C21 1.505(6) . ?
C17 C20 1.527(7) . ?
C17 C19 1.529(7) . ?
C17 C18 1.530(8) . ?

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
C22 O3 C12 116.9(2) . . ?
O2 N1 C15 116.2(3) . . ?
O1 N1 O2 124.0(3) . . ?
O1 N1 C15 119.8(3) . . ?
O6 C13 C12 126.8(3) . . ?
O6 C13 C8 130.1(3) . . ?
C8 C13 C12 102.9(3) . . ?
C5 C6 C7 120.7(3) . . ?
C1 C6 C5 116.5(3) . . ?
C1 C6 C7 122.8(4) . . ?
O3 C22 C23 111.1(3) . . ?
O4 C22 O3 123.1(3) . . ?
O4 C22 C23 125.8(3) . . ?
C3 C2 C1 121.3(4) . . ?
O3 C12 C13 114.1(3) . . ?
O3 C12 C11 114.5(2) . . ?
O3 C12 C15 109.8(3) . . ?
C13 C12 C15 102.9(2) . . ?
C11 C12 C13 106.7(2) . . ?
C11 C12 C15 108.1(3) . . ?
C4 C5 C6 121.0(3) . . ?
C10 C11 C12 124.0(3) . . ?
C6 C7 C8 114.6(3) . . ?
C5 C4 C3 121.9(4) . . ?
N1 C15 C12 105.8(2) . . ?
N1 C15 C14 107.9(2) . . ?
C12 C15 C14 102.3(3) . . ?
C16 C15 N1 108.6(3) . . ?
C16 C15 C12 116.4(3) . . ?
C16 C15 C14 115.2(3) . . ?
C11 C10 C9 117.9(3) . . ?
C11 C10 C17 122.6(3) . . ?
C9 C10 C17 119.5(3) . . ?
C13 C8 C7 115.3(3) . . ?
C13 C8 C14 103.4(2) . . ?
C13 C8 C9 103.6(3) . . ?
C7 C8 C14 115.8(3) . . ?
C7 C8 C9 110.5(3) . . ?
C14 C8 C9 107.2(3) . . ?
C2 C3 C4 117.1(4) . . ?
C2 C3 C21 121.1(4) . . ?
C4 C3 C21 121.8(4) . . ?
C15 C14 C8 108.0(3) . . ?
C2 C1 C6 122.2(4) . . ?
O5 C9 C10 124.2(3) . . ?
O5 C9 C8 120.0(3) . . ?
C10 C9 C8 115.9(3) . . ?
C20 C17 C10 109.0(4) . . ?
C20 C17 C19 109.5(5) . . ?
C20 C17 C18 109.6(4) . . ?
C19 C17 C10 110.9(3) . . ?
C19 C17 C18 108.4(5) . . ?
C18 C17 C10 109.3(4) . . ?

_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_dbr53
_database_code_depnum_ccdc_archive 'CCDC 2365952'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_audit_creation_date             2022-11-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O'
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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5076(6)
_cell_length_b                   12.7385(7)
_cell_length_c                   15.5696(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2084.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5387
_cell_measurement_temperature    298.23
_cell_measurement_theta_max      23.3700
_cell_measurement_theta_min      2.0700
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61606
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14335
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.949
_diffrn_reflns_theta_min         2.066
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      298.23
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  86.00   0.50   11.00    --   16.22  45.00 -30.00  186
  2  ω     -7.00  76.00   0.50   11.00    --   16.22  45.00  60.00  166
  3  ω     -2.00  61.00   0.50   11.00    --   16.22-109.00   4.00  126
  4  ω     40.00  84.00   0.50   11.00    --   16.22-146.00 -61.00   88
  5  ω    -33.00   4.00   0.50   11.00    --  -14.97 -61.00  60.00   74
  6  ω    -61.00  63.00   0.50   11.00    --  -14.97  18.00 -23.00  248
  7  ω    -67.00 -20.00   0.50   11.00    --  -14.97 125.00   0.00   94
  8  ω    -83.00 -47.00   0.50   11.00    --  -14.97 -61.00  60.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0541025000
_diffrn_orient_matrix_UB_12      -0.0040659000
_diffrn_orient_matrix_UB_13      -0.0270047000
_diffrn_orient_matrix_UB_21      0.0401117000
_diffrn_orient_matrix_UB_22      -0.0127474000
_diffrn_orient_matrix_UB_23      -0.0351356000
_diffrn_orient_matrix_UB_31      -0.0054308000
_diffrn_orient_matrix_UB_32      -0.0540399000
_diffrn_orient_matrix_UB_33      0.0104102000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2518
_reflns_number_total             4297
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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         0.420
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 791 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.937
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      0.937
_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)+(0.1068P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1628
_refine_ls_wR_factor_ref         0.1878
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C21(H21A,H21B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C11(H11), C13(H13), C14(H14), C12(H12)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C22(H22A,H22B,
 H22C)
;
_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 0.4698(3) 0.6207(2) 0.43274(19) 0.0581(8) Uani 1 1 d . . . . .
O6 O 0.6785(3) 0.6785(3) 0.3285(2) 0.0717(11) Uani 1 1 d . . . . .
O5 O 0.5664(3) 0.5328(3) 0.0989(2) 0.0718(10) Uani 1 1 d . . . . .
N1 N 0.4225(4) 0.3810(3) 0.3910(3) 0.0603(10) Uani 1 1 d . . . . .
O2 O 0.4024(5) 0.7611(3) 0.3590(2) 0.0945(14) Uani 1 1 d . . . . .
O4 O 0.3474(4) 0.4121(3) 0.4434(3) 0.0914(13) Uani 1 1 d . . . . .
O3 O 0.4156(5) 0.2968(3) 0.3570(3) 0.1092(16) Uani 1 1 d . . . . .
C7 C 0.4090(4) 0.5524(3) 0.2060(3) 0.0514(11) Uani 1 1 d . . . . .
C2 C 0.5387(4) 0.4507(3) 0.3759(3) 0.0490(11) Uani 1 1 d . . . . .
C6 C 0.5401(4) 0.5363(3) 0.1745(3) 0.0515(11) Uani 1 1 d . . . . .
C8 C 0.3908(4) 0.5668(3) 0.2900(3) 0.0535(11) Uani 1 1 d . . . . .
H8 H 0.308175 0.578683 0.309078 0.064 Uiso 1 1 calc R . . . .
C1 C 0.4956(4) 0.5651(3) 0.3559(3) 0.0515(11) Uani 1 1 d . . . . .
C16 C 0.3044(4) 0.5517(4) 0.1395(3) 0.0555(11) Uani 1 1 d . . . . .
H16 H 0.335502 0.591643 0.090020 0.067 Uiso 1 1 calc R . . . .
C4 C 0.6437(4) 0.5195(3) 0.2430(3) 0.0498(11) Uani 1 1 d . . . . .
C10 C 0.8790(5) 0.4688(4) 0.2523(3) 0.0615(13) Uani 1 1 d . . . . .
C5 C 0.6179(5) 0.6030(3) 0.3109(3) 0.0546(12) Uani 1 1 d . . . . .
C9 C 0.7763(4) 0.5226(4) 0.2030(3) 0.0632(13) Uani 1 1 d . . . . .
H9A H 0.771670 0.491076 0.146419 0.076 Uiso 1 1 calc R . . . .
H9B H 0.800508 0.595517 0.195439 0.076 Uiso 1 1 calc R . . . .
C21 C 0.6200(5) 0.4454(4) 0.4572(3) 0.0634(13) Uani 1 1 d . . . . .
H21A H 0.570652 0.471454 0.505287 0.076 Uiso 1 1 calc R . . . .
H21B H 0.693235 0.491012 0.450239 0.076 Uiso 1 1 calc R . . . .
C3 C 0.6078(4) 0.4174(3) 0.2933(3) 0.0524(11) Uani 1 1 d . . . . .
H3A H 0.552898 0.373395 0.258575 0.063 Uiso 1 1 calc R . . . .
H3B H 0.683998 0.377982 0.307363 0.063 Uiso 1 1 calc R . . . .
C19 C 0.4297(6) 0.7212(4) 0.4257(4) 0.0678(14) Uani 1 1 d . . . . .
C17 C 0.2791(6) 0.4420(4) 0.1088(4) 0.0771(16) Uani 1 1 d . . . . .
H17A H 0.356697 0.411606 0.087754 0.116 Uiso 1 1 calc GR . . . .
H17B H 0.217236 0.443656 0.063422 0.116 Uiso 1 1 calc GR . . . .
H17C H 0.247165 0.400423 0.155504 0.116 Uiso 1 1 calc GR . . . .
C15 C 0.9293(5) 0.5099(5) 0.3276(4) 0.0760(15) Uani 1 1 d . . . . .
H15 H 0.900403 0.574188 0.348045 0.091 Uiso 1 1 calc R . . . .
C11 C 0.9283(6) 0.3745(5) 0.2219(4) 0.0803(16) Uani 1 1 d . . . . .
H11 H 0.896757 0.346116 0.171126 0.096 Uiso 1 1 calc R . . . .
C18 C 0.1850(5) 0.6055(5) 0.1704(4) 0.0823(17) Uani 1 1 d . . . . .
H18A H 0.143722 0.562259 0.212590 0.123 Uiso 1 1 calc GR . . . .
H18B H 0.128588 0.616522 0.122797 0.123 Uiso 1 1 calc GR . . . .
H18C H 0.206717 0.671877 0.195645 0.123 Uiso 1 1 calc GR . . . .
C20 C 0.4237(7) 0.7722(4) 0.5112(4) 0.089(2) Uani 1 1 d . . . . .
H20A H 0.356376 0.741229 0.544324 0.134 Uiso 1 1 calc GR . . . .
H20B H 0.407590 0.845884 0.504175 0.134 Uiso 1 1 calc GR . . . .
H20C H 0.503213 0.762525 0.540536 0.134 Uiso 1 1 calc GR . . . .
C13 C 1.0688(6) 0.3619(7) 0.3388(5) 0.101(2) Uani 1 1 d . . . . .
H13 H 1.133055 0.326022 0.367574 0.121 Uiso 1 1 calc R . . . .
C14 C 1.0224(6) 0.4558(6) 0.3726(4) 0.095(2) Uani 1 1 d . . . . .
H14 H 1.053273 0.481686 0.424410 0.114 Uiso 1 1 calc R . . . .
C12 C 1.0224(6) 0.3227(5) 0.2655(5) 0.098(2) Uani 1 1 d . . . . .
H12 H 1.054158 0.259765 0.244091 0.118 Uiso 1 1 calc R . . . .
C22 C 0.6670(7) 0.3331(5) 0.4780(4) 0.097(2) Uani 1 1 d . . . . .
H22A H 0.721369 0.308819 0.432685 0.146 Uiso 1 1 calc GR . . . .
H22B H 0.595130 0.286987 0.483287 0.146 Uiso 1 1 calc GR . . . .
H22C H 0.713456 0.333909 0.531113 0.146 Uiso 1 1 calc GR . . . .


_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 1.416(5) . ?
O1 C19 1.352(6) . ?
O6 C5 1.185(5) . ?
O5 C6 1.209(5) . ?
N1 O4 1.202(5) . ?
N1 O3 1.199(5) . ?
N1 C2 1.528(6) . ?
O2 C19 1.191(6) . ?
C7 C6 1.477(6) . ?
C7 C8 1.336(6) . ?
C7 C16 1.510(6) . ?
C2 C1 1.557(6) . ?
C2 C21 1.529(6) . ?
C2 C3 1.536(6) . ?
C6 C4 1.540(6) . ?
C8 H8 0.9300 . ?
C8 C1 1.505(6) . ?
C1 C5 1.541(7) . ?
C16 H16 0.9800 . ?
C16 C17 1.501(7) . ?
C16 C18 1.508(7) . ?
C4 C5 1.524(6) . ?
C4 C9 1.527(6) . ?
C4 C3 1.564(6) . ?
C10 C9 1.490(7) . ?
C10 C15 1.389(7) . ?
C10 C11 1.392(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.547(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C19 C20 1.483(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C14 1.385(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(8) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C13 H13 0.9300 . ?
C13 C14 1.396(10) . ?
C13 C12 1.337(9) . ?
C14 H14 0.9300 . ?
C12 H12 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 O1 C1 117.7(4) . . ?
O4 N1 C2 116.0(4) . . ?
O3 N1 O4 123.7(4) . . ?
O3 N1 C2 120.0(4) . . ?
C6 C7 C16 116.8(4) . . ?
C8 C7 C6 118.6(4) . . ?
C8 C7 C16 124.6(4) . . ?
N1 C2 C1 110.0(4) . . ?
N1 C2 C21 107.1(3) . . ?
N1 C2 C3 110.3(4) . . ?
C21 C2 C1 111.7(3) . . ?
C21 C2 C3 114.6(4) . . ?
C3 C2 C1 103.2(3) . . ?
O5 C6 C7 122.8(4) . . ?
O5 C6 C4 120.6(4) . . ?
C7 C6 C4 116.6(4) . . ?
C7 C8 H8 117.9 . . ?
C7 C8 C1 124.1(4) . . ?
C1 C8 H8 117.9 . . ?
O1 C1 C2 110.8(3) . . ?
O1 C1 C8 115.4(4) . . ?
O1 C1 C5 112.8(4) . . ?
C8 C1 C2 111.2(3) . . ?
C8 C1 C5 107.2(3) . . ?
C5 C1 C2 98.2(3) . . ?
C7 C16 H16 107.0 . . ?
C17 C16 C7 110.7(4) . . ?
C17 C16 H16 107.0 . . ?
C17 C16 C18 112.2(5) . . ?
C18 C16 C7 112.6(4) . . ?
C18 C16 H16 107.0 . . ?
C6 C4 C3 107.0(3) . . ?
C5 C4 C6 104.9(4) . . ?
C5 C4 C9 115.3(4) . . ?
C5 C4 C3 101.0(3) . . ?
C9 C4 C6 111.0(4) . . ?
C9 C4 C3 116.5(4) . . ?
C15 C10 C9 122.5(5) . . ?
C15 C10 C11 118.1(5) . . ?
C11 C10 C9 119.5(5) . . ?
O6 C5 C1 126.7(4) . . ?
O6 C5 C4 129.1(4) . . ?
C4 C5 C1 104.2(4) . . ?
C4 C9 H9A 108.3 . . ?
C4 C9 H9B 108.3 . . ?
C10 C9 C4 116.0(4) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C2 C21 H21A 108.9 . . ?
C2 C21 H21B 108.9 . . ?
C2 C21 C22 113.1(4) . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C2 C3 C4 107.7(3) . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
O1 C19 C20 110.8(5) . . ?
O2 C19 O1 123.3(5) . . ?
O2 C19 C20 125.8(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.6(6) . . ?
C14 C15 H15 119.7 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 H11 119.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.9(6) . . ?
C15 C14 C13 118.8(7) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(7) . . ?
C13 C12 H12 119.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_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 2.790
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_dbr64
_database_code_depnum_ccdc_archive 'CCDC 2360361'
loop_
_audit_author_name
_audit_author_address
'Raghavaiah Pallepogu'
;Central University of Karnataka
India
;
_audit_update_record             
;
2024-06-04 deposited with the CCDC.	2025-04-24 downloaded from the CCDC.
;
_audit_creation_date             2023-09-08
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2018.12.18 svn.r3554 for Rigaku Oxford Diffraction, GUI svn.r1)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 Br N O6'
_chemical_formula_sum            'C21 H22 Br N O6'
_chemical_formula_weight         464.30
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Br'
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'
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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.0203(7)
_cell_length_b                   10.9547(10)
_cell_length_c                   28.092(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2160.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5366
_cell_measurement_temperature    234
_cell_measurement_theta_max      26.4770
_cell_measurement_theta_min      2.3390
_shelx_estimated_absorpt_T_max   0.749
_shelx_estimated_absorpt_T_min   0.723
_exptl_absorpt_coefficient_mu    1.938
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64522
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic orangish orange'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.179
_exptl_crystal_size_mid          0.169
_exptl_crystal_size_min          0.158
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0578
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            11339
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.211
_diffrn_reflns_theta_min         2.358
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      234
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  74.00   0.50   17.75    --   16.22 -15.00 -90.00  256
  2  ω    -87.00 -36.00   0.50   17.75    --  -15.60 158.00-144.00  102
  3  ω     32.00  75.00   0.50   17.75    --   16.22-134.00  74.00   86
  4  ω    -25.00  15.00   0.50   17.75    --   16.22 -10.00 111.00   80
  5  ω      6.00  35.00   0.50   17.75    --  -15.60  77.00 150.00   58
  6  ω    -45.00 -20.00   0.50   17.75    --  -15.60  77.00 150.00   50
  7  ω    -79.00   9.00   0.50   17.75    --  -15.60 -61.00 120.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0185391000
_diffrn_orient_matrix_UB_12      -0.0601146000
_diffrn_orient_matrix_UB_13      0.0080410000
_diffrn_orient_matrix_UB_21      0.0066311000
_diffrn_orient_matrix_UB_22      -0.0201807000
_diffrn_orient_matrix_UB_23      -0.0239741000
_diffrn_orient_matrix_UB_31      0.0990083000
_diffrn_orient_matrix_UB_32      0.0129109000
_diffrn_orient_matrix_UB_33      0.0000947000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                2591
_reflns_number_total             4479
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_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         0.578
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 698 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(9)
_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     266
_refine_ls_number_reflns         4479
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0605
_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)+(0.0394P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1085
_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:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C4(H4), C13(H13), C15(H15), C14(H14)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.39090(9) 0.50599(7) 0.50978(2) 0.0700(3) Uani 1 1 d . . . . .
O1 O 0.7447(6) 0.7705(4) 0.72286(14) 0.0500(11) Uani 1 1 d . . . . .
O4 O 0.5370(6) 0.8999(4) 0.54217(15) 0.0618(12) Uani 1 1 d . . . . .
O3 O 0.9512(6) 0.7565(4) 0.63159(15) 0.0596(12) Uani 1 1 d . . . . .
N1 N 0.5924(9) 0.5630(5) 0.69050(19) 0.0561(15) Uani 1 1 d . . . . .
O5 O 0.7414(8) 0.5352(4) 0.67185(19) 0.0845(16) Uani 1 1 d . . . . .
O2 O 0.9152(7) 0.9416(5) 0.71265(19) 0.0827(15) Uani 1 1 d . . . . .
C8 C 0.7810(8) 0.7550(5) 0.6343(2) 0.0383(14) Uani 1 1 d . . . . .
O6 O 0.5150(7) 0.5009(5) 0.71968(18) 0.0978(16) Uani 1 1 d . . . . .
C5 C 0.6571(8) 0.7818(5) 0.6776(2) 0.0371(14) Uani 1 1 d . . . . .
C12 C 0.6607(12) 0.3336(6) 0.5400(3) 0.068(2) Uani 1 1 d . . . . .
H12 H 0.569586 0.278032 0.528503 0.081 Uiso 1 1 calc R . . . .
C2 C 0.5647(8) 0.8670(5) 0.5829(2) 0.0448(16) Uani 1 1 d . . . . .
C7 C 0.4707(7) 0.6696(5) 0.61958(18) 0.0379(14) Uani 1 1 d . . . . .
H7A H 0.348160 0.704833 0.610092 0.045 Uiso 1 1 calc R . . . .
H7B H 0.471361 0.583009 0.610835 0.045 Uiso 1 1 calc R . . . .
C11 C 0.6285(9) 0.4565(5) 0.5372(2) 0.0503(17) Uani 1 1 d . . . . .
C10 C 0.7544(9) 0.5429(5) 0.5526(2) 0.0429(16) Uani 1 1 d . . . . .
C6 C 0.5001(8) 0.6840(5) 0.6740(2) 0.0404(15) Uani 1 1 d . . . . .
C3 C 0.5244(9) 0.9454(5) 0.6249(2) 0.0454(16) Uani 1 1 d . . . . .
C1 C 0.6366(7) 0.7375(4) 0.59424(18) 0.0343(13) Uani 1 1 d . . . . .
C4 C 0.5693(8) 0.9041(5) 0.6685(2) 0.0449(16) Uani 1 1 d . . . . .
H4 H 0.544118 0.954806 0.694698 0.054 Uiso 1 1 calc R . . . .
C18 C 0.4291(12) 1.0660(5) 0.6147(2) 0.066(2) Uani 1 1 d . . . . .
H18 H 0.481517 1.096152 0.584142 0.080 Uiso 1 1 calc R . . . .
C13 C 0.8251(14) 0.2932(7) 0.5594(3) 0.078(3) Uani 1 1 d . . . . .
H13 H 0.847601 0.208886 0.562199 0.094 Uiso 1 1 calc R . . . .
C15 C 0.9258(8) 0.5002(6) 0.5713(2) 0.0575(16) Uani 1 1 d . . . . .
H15 H 1.018820 0.556133 0.581388 0.069 Uiso 1 1 calc R . . . .
C9 C 0.7204(9) 0.6781(5) 0.5491(2) 0.0425(16) Uani 1 1 d . . . . .
H9A H 0.633462 0.693420 0.522460 0.051 Uiso 1 1 calc R . . . .
H9B H 0.841607 0.718158 0.541645 0.051 Uiso 1 1 calc R . . . .
C21 C 0.3234(8) 0.7051(6) 0.7030(2) 0.0590(18) Uani 1 1 d . . . . .
H21A H 0.234115 0.639028 0.697558 0.088 Uiso 1 1 calc GR . . . .
H21B H 0.265497 0.781871 0.693668 0.088 Uiso 1 1 calc GR . . . .
H21C H 0.356634 0.708131 0.736492 0.088 Uiso 1 1 calc GR . . . .
C16 C 0.8750(11) 0.8555(7) 0.7358(2) 0.062(2) Uani 1 1 d . . . . .
C14 C 0.9605(11) 0.3759(7) 0.5751(3) 0.076(2) Uani 1 1 d . . . . .
H14 H 1.075543 0.347901 0.588243 0.091 Uiso 1 1 calc R . . . .
C17 C 0.9552(10) 0.8234(8) 0.7840(2) 0.090(3) Uani 1 1 d . . . . .
H17A H 0.877194 0.860192 0.808626 0.135 Uiso 1 1 calc GR . . . .
H17B H 1.084451 0.854032 0.786468 0.135 Uiso 1 1 calc GR . . . .
H17C H 0.955468 0.735447 0.787879 0.135 Uiso 1 1 calc GR . . . .
C20 C 0.4748(13) 1.1619(6) 0.6523(3) 0.107(3) Uani 1 1 d . . . . .
H20A H 0.410971 1.141109 0.681842 0.160 Uiso 1 1 calc GR . . . .
H20B H 0.431263 1.241247 0.641483 0.160 Uiso 1 1 calc GR . . . .
H20C H 0.611340 1.164521 0.657578 0.160 Uiso 1 1 calc GR . . . .
C19 C 0.2190(13) 1.0491(7) 0.6076(3) 0.117(3) Uani 1 1 d . . . . .
H19A H 0.197115 0.990288 0.582432 0.175 Uiso 1 1 calc GR . . . .
H19B H 0.161656 1.126609 0.599015 0.175 Uiso 1 1 calc GR . . . .
H19C H 0.162213 1.019634 0.636952 0.175 Uiso 1 1 calc GR . . . .


_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 C11 1.916(6) . ?
O1 C5 1.417(6) . ?
O1 C16 1.355(7) . ?
O4 C2 1.215(6) . ?
O3 C8 1.197(6) . ?
N1 O5 1.209(6) . ?
N1 O6 1.196(6) . ?
N1 C6 1.547(7) . ?
O2 C16 1.180(7) . ?
C8 C5 1.525(7) . ?
C8 C1 1.527(7) . ?
C5 C6 1.540(7) . ?
C5 C4 1.497(7) . ?
C12 H12 0.9400 . ?
C12 C11 1.367(7) . ?
C12 C13 1.351(9) . ?
C2 C3 1.486(8) . ?
C2 C1 1.539(7) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 C6 1.550(7) . ?
C7 C1 1.554(7) . ?
C11 C10 1.365(7) . ?
C10 C15 1.394(8) . ?
C10 C9 1.503(7) . ?
C6 C21 1.502(7) . ?
C3 C4 1.343(8) . ?
C3 C18 1.508(8) . ?
C1 C9 1.542(7) . ?
C4 H4 0.9400 . ?
C18 H18 0.9900 . ?
C18 C20 1.525(9) . ?
C18 C19 1.500(10) . ?
C13 H13 0.9400 . ?
C13 C14 1.385(9) . ?
C15 H15 0.9400 . ?
C15 C14 1.387(9) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 H21C 0.9700 . ?
C16 C17 1.507(9) . ?
C14 H14 0.9400 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 H17C 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19C 0.9700 . ?

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
C16 O1 C5 118.3(5) . . ?
O5 N1 C6 116.6(5) . . ?
O6 N1 O5 123.2(6) . . ?
O6 N1 C6 120.2(6) . . ?
O3 C8 C5 128.1(6) . . ?
O3 C8 C1 128.1(5) . . ?
C5 C8 C1 103.5(4) . . ?
O1 C5 C8 116.8(4) . . ?
O1 C5 C6 108.0(4) . . ?
O1 C5 C4 114.3(5) . . ?
C8 C5 C6 102.8(4) . . ?
C4 C5 C8 105.7(5) . . ?
C4 C5 C6 108.4(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C13 C12 C11 119.2(8) . . ?
O4 C2 C3 123.0(5) . . ?
O4 C2 C1 121.4(6) . . ?
C3 C2 C1 115.5(5) . . ?
H7A C7 H7B 108.5 . . ?
C6 C7 H7A 110.2 . . ?
C6 C7 H7B 110.2 . . ?
C6 C7 C1 107.7(4) . . ?
C1 C7 H7A 110.2 . . ?
C1 C7 H7B 110.2 . . ?
C12 C11 Br1 116.4(6) . . ?
C10 C11 Br1 119.7(4) . . ?
C10 C11 C12 123.9(6) . . ?
C11 C10 C15 116.4(5) . . ?
C11 C10 C9 124.0(5) . . ?
C15 C10 C9 119.5(6) . . ?
N1 C6 C7 105.3(4) . . ?
C5 C6 N1 106.0(4) . . ?
C5 C6 C7 103.4(4) . . ?
C21 C6 N1 108.4(5) . . ?
C21 C6 C5 116.6(5) . . ?
C21 C6 C7 116.2(5) . . ?
C2 C3 C18 116.1(6) . . ?
C4 C3 C2 118.9(5) . . ?
C4 C3 C18 124.9(6) . . ?
C8 C1 C2 104.7(4) . . ?
C8 C1 C7 102.7(4) . . ?
C8 C1 C9 113.9(5) . . ?
C2 C1 C7 106.9(4) . . ?
C2 C1 C9 110.1(4) . . ?
C9 C1 C7 117.4(4) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 C5 123.7(5) . . ?
C3 C4 H4 118.1 . . ?
C3 C18 H18 107.0 . . ?
C3 C18 C20 112.3(6) . . ?
C20 C18 H18 107.0 . . ?
C19 C18 C3 110.7(6) . . ?
C19 C18 H18 107.0 . . ?
C19 C18 C20 112.5(7) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(7) . . ?
C14 C13 H13 120.0 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.7(7) . . ?
C14 C15 H15 119.6 . . ?
C10 C9 C1 115.0(5) . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C1 C9 H9A 108.5 . . ?
C1 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
C6 C21 H21A 109.5 . . ?
C6 C21 H21B 109.5 . . ?
C6 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 C16 C17 109.5(7) . . ?
O2 C16 O1 124.2(7) . . ?
O2 C16 C17 126.3(8) . . ?
C13 C14 C15 119.8(7) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 . . ?

_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 1.877
_oxdiff_exptl_absorpt_empirical_full_min 0.593
