# 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_HP_20250619_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2473915'
loop_
_audit_author_name
_audit_author_address
'Anil Kumar Saikia'
;IIT Guwahati, India
India
;
_audit_update_record             
;
2025-10-15 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H Br Cl N O'
_chemical_formula_weight         158.39

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.170(4)
_cell_length_b                   10.005(5)
_cell_length_c                   20.716(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.746(13)
_cell_angle_gamma                90
_cell_volume                     1867.4(15)
_cell_formula_units_Z            17
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.394
_exptl_crystal_F_000             1258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.98
_exptl_crystal_size_mid          0.78
_exptl_crystal_size_min          0.54
_exptl_absorpt_coefficient_mu    9.779
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42537
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.001
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3249
_reflns_number_gt                2803
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+1.1952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3249
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.1065
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   0.725
_refine_ls_restrained_S_all      0.725
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br01 Br 1.19521(3) 0.92202(3) 0.33079(2) 0.07391(16) Uani 1 1 d . . . . .
Cl02 Cl 1.04029(8) 0.32850(8) 0.26422(4) 0.0806(3) Uani 1 1 d . . . . .
O003 O 0.5034(2) 0.39559(18) 0.37277(9) 0.0617(4) Uani 1 1 d . . . . .
O004 O 0.3044(2) 0.6745(2) 0.47362(11) 0.0737(5) Uani 1 1 d . . . . .
O005 O 0.3193(2) 0.4457(2) 0.42407(11) 0.0760(6) Uani 1 1 d . . . . .
N006 N 0.6743(2) 0.9788(2) 0.46445(10) 0.0563(5) Uani 1 1 d . . . . .
N007 N 0.4817(2) 0.8246(2) 0.47135(10) 0.0553(5) Uani 1 1 d . . . . .
C008 C 0.6932(2) 0.7751(2) 0.41909(10) 0.0462(5) Uani 1 1 d . . . . .
C009 C 0.7332(2) 0.5607(2) 0.36765(11) 0.0455(5) Uani 1 1 d . . . . .
C00A C 0.6405(2) 0.6476(2) 0.40210(10) 0.0473(5) Uani 1 1 d . . . . .
C00B C 0.5044(3) 0.6094(3) 0.41913(11) 0.0510(5) Uani 1 1 d . . . . .
C00C C 0.8189(3) 0.8557(2) 0.40901(10) 0.0475(5) Uani 1 1 d . . . . .
C00D C 0.8620(2) 0.5051(2) 0.40285(12) 0.0534(5) Uani 1 1 d . . . . .
H00D H 0.885128 0.516674 0.448151 0.064 Uiso 1 1 calc R U . . .
C00E C 0.6082(3) 0.8578(2) 0.45330(11) 0.0501(5) Uani 1 1 d . . . . .
C00F C 0.9389(2) 0.8362(2) 0.37760(11) 0.0496(5) Uani 1 1 d . . . . .
H00F H 0.954546 0.754476 0.358649 0.060 Uiso 1 1 calc R U . . .
C00G C 0.9565(3) 0.4328(2) 0.37156(14) 0.0568(6) Uani 1 1 d . . . . .
H00G H 1.042984 0.395680 0.395427 0.068 Uiso 1 1 calc R U . . .
C00H C 0.8005(3) 0.9814(2) 0.43706(11) 0.0510(5) Uani 1 1 d . . . . .
C00I C 1.0343(3) 0.9430(3) 0.37558(12) 0.0548(6) Uani 1 1 d . . . . .
C00J C 0.9210(3) 0.4167(2) 0.30476(14) 0.0548(6) Uani 1 1 d . . . . .
C00K C 0.4339(3) 0.4783(3) 0.40554(12) 0.0560(6) Uani 1 1 d . . . . .
C00L C 0.7002(3) 0.5423(3) 0.30018(12) 0.0544(6) Uani 1 1 d . . . . .
H00L H 0.614022 0.579121 0.275896 0.065 Uiso 1 1 calc R U . . .
C00M C 0.7941(3) 0.4700(3) 0.26890(12) 0.0580(6) Uani 1 1 d . . . . .
H00M H 0.771381 0.457415 0.223653 0.070 Uiso 1 1 calc R U . . .
C00N C 0.8972(3) 1.0866(2) 0.43503(13) 0.0603(6) Uani 1 1 d . . . . .
H00N H 0.883335 1.168583 0.454191 0.072 Uiso 1 1 calc R U . . .
C00O C 0.4316(3) 0.7036(3) 0.45427(12) 0.0555(6) Uani 1 1 d . . . . .
C00P C 1.0151(3) 1.0655(3) 0.40351(13) 0.0605(6) Uani 1 1 d . . . . .
H00P H 1.082152 1.134246 0.401073 0.073 Uiso 1 1 calc R U . . .
C00Q C 0.4386(3) 0.2639(3) 0.35782(15) 0.0681(7) Uani 1 1 d . . . . .
H00A H 0.337754 0.271953 0.333558 0.082 Uiso 1 1 calc R U . . .
H00B H 0.436527 0.214952 0.398069 0.082 Uiso 1 1 calc R U . . .
C00R C 0.5321(4) 0.1934(3) 0.31793(18) 0.0820(8) Uani 1 1 d . . . . .
H00C H 0.531445 0.241765 0.277852 0.123 Uiso 1 1 calc R U . . .
H00E H 0.493653 0.105077 0.307873 0.123 Uiso 1 1 calc R U . . .
H00H H 0.631894 0.187637 0.342131 0.123 Uiso 1 1 calc R U . . .
H1 H 0.643(3) 1.043(3) 0.4821(15) 0.065(8) Uiso 1 1 d . . . . .
H2 H 0.279(5) 0.595(4) 0.462(2) 0.110(15) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C00I 1.896(2) . ?
Cl02 C00J 1.738(2) . ?
O003 C00K 1.308(3) . ?
O003 C00Q 1.455(3) . ?
O004 C00O 1.334(3) . ?
O005 C00K 1.229(3) . ?
N006 C00E 1.354(4) . ?
N006 C00H 1.380(3) . ?
N007 C00O 1.320(3) . ?
N007 C00E 1.326(3) . ?
C008 C00A 1.386(3) . ?
C008 C00E 1.414(3) . ?
C008 C00C 1.454(3) . ?
C009 C00D 1.383(3) . ?
C009 C00L 1.386(4) . ?
C009 C00A 1.488(3) . ?
C00A C00B 1.412(3) . ?
C00B C00O 1.430(3) . ?
C00B C00K 1.467(4) . ?
C00C C00F 1.392(3) . ?
C00C C00H 1.408(3) . ?
C00D C00G 1.380(3) . ?
C00F C00I 1.386(4) . ?
C00G C00J 1.371(4) . ?
C00H C00N 1.383(4) . ?
C00I C00P 1.380(4) . ?
C00J C00M 1.367(4) . ?
C00L C00M 1.376(3) . ?
C00N C00P 1.380(4) . ?
C00Q C00R 1.476(4) . ?

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
C00K O003 C00Q 117.6(2) . . ?
C00E N006 C00H 109.2(2) . . ?
C00O N007 C00E 115.7(2) . . ?
C00A C008 C00E 117.9(2) . . ?
C00A C008 C00C 136.2(2) . . ?
C00E C008 C00C 105.9(2) . . ?
C00D C009 C00L 118.9(2) . . ?
C00D C009 C00A 119.3(2) . . ?
C00L C009 C00A 121.6(2) . . ?
C008 C00A C00B 117.9(2) . . ?
C008 C00A C009 117.2(2) . . ?
C00B C00A C009 124.9(2) . . ?
C00A C00B C00O 117.9(2) . . ?
C00A C00B C00K 124.9(2) . . ?
C00O C00B C00K 117.2(2) . . ?
C00F C00C C00H 119.0(2) . . ?
C00F C00C C008 135.0(2) . . ?
C00H C00C C008 106.02(19) . . ?
C00G C00D C009 120.8(2) . . ?
N007 C00E N006 124.3(2) . . ?
N007 C00E C008 126.0(2) . . ?
N006 C00E C008 109.7(2) . . ?
C00I C00F C00C 117.6(2) . . ?
C00J C00G C00D 119.0(2) . . ?
N006 C00H C00N 128.2(2) . . ?
N006 C00H C00C 109.1(2) . . ?
C00N C00H C00C 122.7(2) . . ?
C00P C00I C00F 122.8(2) . . ?
C00P C00I Br01 118.4(2) . . ?
C00F C00I Br01 118.83(18) . . ?
C00M C00J C00G 121.4(2) . . ?
C00M C00J Cl02 119.0(2) . . ?
C00G C00J Cl02 119.7(2) . . ?
O005 C00K O003 121.5(2) . . ?
O005 C00K C00B 123.3(2) . . ?
O003 C00K C00B 115.2(2) . . ?
C00M C00L C009 120.4(2) . . ?
C00J C00M C00L 119.6(2) . . ?
C00P C00N C00H 117.5(2) . . ?
N007 C00O O004 113.6(2) . . ?
N007 C00O C00B 124.7(2) . . ?
O004 C00O C00B 121.8(2) . . ?
C00N C00P C00I 120.4(2) . . ?
O003 C00Q C00R 107.1(2) . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_aks25045_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2512454'
loop_
_audit_author_name
_audit_author_address
'Anil Kumar Saikia'
;Indian Institute of Technology Guwahati, India
India
;
_audit_update_record             
;
2025-12-01 deposited with the CCDC.	2026-04-29 downloaded from the CCDC.
;
_audit_creation_date             2025-10-13
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2023.11.24 svn.r209d9fb2 for OlexSys, GUI svn.r6869)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N O6'
_chemical_formula_sum            'C22 H17 N O6'
_chemical_formula_weight         391.36
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3089(8)
_cell_length_b                   11.9791(8)
_cell_length_c                   13.5487(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.785(2)
_cell_angle_gamma                90
_cell_volume                     1902.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.01
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.7033
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1303 before and 0.0713 after correction.
The Ratio of minimum to maximum transmission is 0.9439.
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    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   0.7451
_exptl_transmission_factor_min   0.7033
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            44627
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.047
_diffrn_reflns_theta_max         25.047
_diffrn_reflns_theta_min         1.958
_diffrn_ambient_temperature      296.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2559
_reflns_number_total             3355
_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 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0761
_refine_ls_restrained_S_all      1.201
_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)+(0.0357P)²+1.7510P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1496
_refine_ls_wR_factor_ref         0.1641
_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 Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5a), C16(H16), C17(H17), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C22(H22a,H22b,H22c)
2.d Idealised tetrahedral OH refined as rotating group:
 O5(H5)
;
_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
O1 O 0.31658(19) 0.3658(2) -0.15075(15) 0.0624(6) Uani 1 1 d . . . . .
O2 O 0.5850(2) 0.3612(3) 0.5674(2) 0.1144(12) Uani 1 1 d . . . . .
O3 O 0.4281(3) 0.0195(2) 0.2076(2) 0.0849(8) Uani 1 1 d . . . . .
O4 O 0.3914(2) -0.0919(2) 0.0717(2) 0.0850(8) Uani 1 1 d . . . . .
O5 O 0.3480(2) -0.0092(2) -0.10746(19) 0.0816(8) Uani 1 1 d . . . . .
H5 H 0.359570 -0.057420 -0.062437 0.122 Uiso 1 1 calc R U . . .
O6 O 0.4012(2) 0.3515(2) 0.54722(16) 0.0763(8) Uani 1 1 d . . . . .
N1 N 0.3325(2) 0.1748(2) -0.13170(19) 0.0582(7) Uani 1 1 d . . . . .
C1 C 0.3591(2) 0.4217(3) 0.0193(2) 0.0503(7) Uani 1 1 d . . . . .
C2 C 0.3761(3) 0.5027(3) 0.0949(2) 0.0639(9) Uani 1 1 d . . . . .
H2 H 0.396378 0.483158 0.164637 0.077 Uiso 1 1 calc R U . . .
C3 C 0.3624(3) 0.6134(3) 0.0650(3) 0.0788(11) Uani 1 1 d . . . . .
H3 H 0.374454 0.668740 0.115351 0.095 Uiso 1 1 calc R U . . .
C4 C 0.3312(3) 0.6434(3) -0.0383(3) 0.0829(12) Uani 1 1 d . . . . .
H4 H 0.322478 0.718602 -0.055990 0.100 Uiso 1 1 calc R U . . .
C5 C 0.3129(3) 0.5651(3) -0.1154(3) 0.0748(10) Uani 1 1 d . . . . .
H5A H 0.290766 0.584794 -0.185100 0.090 Uiso 1 1 calc R U . . .
C6 C 0.3290(3) 0.4561(3) -0.0838(2) 0.0577(8) Uani 1 1 d . . . . .
C7 C 0.3389(2) 0.2738(3) -0.0893(2) 0.0508(8) Uani 1 1 d . . . . .
C8 C 0.3649(2) 0.3009(2) 0.0156(2) 0.0452(7) Uani 1 1 d . . . . .
C9 C 0.3532(3) 0.0914(3) -0.0639(3) 0.0575(8) Uani 1 1 d . . . . .
C10 C 0.3796(2) 0.1045(3) 0.0454(2) 0.0507(7) Uani 1 1 d . . . . .
C11 C 0.3860(2) 0.2132(2) 0.0858(2) 0.0449(7) Uani 1 1 d . . . . .
C12 C 0.3992(3) 0.0023(3) 0.1076(3) 0.0645(9) Uani 1 1 d . . . . .
C13 C 0.4625(5) -0.0774(4) 0.2753(4) 0.1107(16) Uani 1 1 d . . . . .
H13A H 0.400857 -0.131385 0.260777 0.133 Uiso 1 1 calc R U . . .
H13B H 0.528425 -0.112928 0.263813 0.133 Uiso 1 1 calc R U . . .
C14 C 0.4892(7) -0.0407(5) 0.3779(4) 0.170(3) Uani 1 1 d . . . . .
H14A H 0.519736 -0.101689 0.423987 0.255 Uiso 1 1 calc R U . . .
H14B H 0.421464 -0.013180 0.390641 0.255 Uiso 1 1 calc R U . . .
H14C H 0.544772 0.018036 0.389538 0.255 Uiso 1 1 calc R U . . .
C15 C 0.4128(2) 0.2419(2) 0.1985(2) 0.0451(7) Uani 1 1 d . . . . .
C16 C 0.3264(3) 0.2580(3) 0.2413(2) 0.0660(10) Uani 1 1 d . . . . .
H16 H 0.251120 0.246346 0.201182 0.079 Uiso 1 1 calc R U . . .
C17 C 0.3500(3) 0.2912(3) 0.3432(2) 0.0641(9) Uani 1 1 d . . . . .
H17 H 0.290545 0.302329 0.371061 0.077 Uiso 1 1 calc R U . . .
C18 C 0.4608(2) 0.3078(3) 0.4037(2) 0.0486(7) Uani 1 1 d . . . . .
C19 C 0.5470(3) 0.2913(3) 0.3605(2) 0.0625(9) Uani 1 1 d . . . . .
H19 H 0.622321 0.302289 0.400622 0.075 Uiso 1 1 calc R U . . .
C20 C 0.5235(3) 0.2587(3) 0.2591(2) 0.0601(9) Uani 1 1 d . . . . .
H20 H 0.582939 0.247932 0.231157 0.072 Uiso 1 1 calc R U . . .
C21 C 0.4904(3) 0.3433(3) 0.5139(2) 0.0600(9) Uani 1 1 d . . . . .
C22 C 0.4229(4) 0.3840(4) 0.6540(3) 0.0938(14) Uani 1 1 d . . . . .
H22A H 0.354532 0.375221 0.673218 0.141 Uiso 1 1 calc R U . . .
H22B H 0.446660 0.460687 0.662366 0.141 Uiso 1 1 calc R U . . .
H22C H 0.482049 0.337775 0.697504 0.141 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 C6 1.390(4) . ?
O1 C7 1.358(4) . ?
O2 C21 1.188(4) . ?
O3 C12 1.308(4) . ?
O3 C13 1.460(5) . ?
O4 C12 1.222(4) . ?
O5 H5 0.8200 . ?
O5 C9 1.335(4) . ?
O6 C21 1.312(4) . ?
O6 C22 1.442(4) . ?
N1 C7 1.309(4) . ?
N1 C9 1.328(4) . ?
C1 C2 1.380(4) . ?
C1 C6 1.394(4) . ?
C1 C8 1.449(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.381(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(5) . ?
C5 H5A 0.9300 . ?
C5 C6 1.369(5) . ?
C7 C8 1.396(4) . ?
C8 C11 1.389(4) . ?
C9 C10 1.425(4) . ?
C10 C11 1.406(4) . ?
C10 C12 1.463(5) . ?
C11 C15 1.499(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.398(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.372(4) . ?
C15 C20 1.373(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.380(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.375(4) . ?
C18 C19 1.374(4) . ?
C18 C21 1.487(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.372(4) . ?
C20 H20 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
C7 O1 C6 105.7(2) . . ?
C12 O3 C13 117.4(3) . . ?
C9 O5 H5 109.5 . . ?
C21 O6 C22 116.6(3) . . ?
C7 N1 C9 113.9(3) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C8 136.8(3) . . ?
C6 C1 C8 105.2(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.7(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(4) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 H5A 121.9 . . ?
C6 C5 C4 116.1(3) . . ?
C6 C5 H5A 121.9 . . ?
O1 C6 C1 111.5(3) . . ?
C5 C6 O1 124.2(3) . . ?
C5 C6 C1 124.4(3) . . ?
O1 C7 C8 112.1(3) . . ?
N1 C7 O1 119.5(3) . . ?
N1 C7 C8 128.5(3) . . ?
C7 C8 C1 105.6(3) . . ?
C11 C8 C1 137.1(3) . . ?
C11 C8 C7 117.3(3) . . ?
O5 C9 C10 121.5(3) . . ?
N1 C9 O5 113.6(3) . . ?
N1 C9 C10 124.8(3) . . ?
C9 C10 C12 116.9(3) . . ?
C11 C10 C9 118.4(3) . . ?
C11 C10 C12 124.7(3) . . ?
C8 C11 C10 117.2(2) . . ?
C8 C11 C15 117.5(3) . . ?
C10 C11 C15 125.3(3) . . ?
O3 C12 C10 114.2(3) . . ?
O4 C12 O3 121.4(3) . . ?
O4 C12 C10 124.3(3) . . ?
O3 C13 H13A 110.1 . . ?
O3 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C14 C13 O3 108.0(4) . . ?
C14 C13 H13A 110.1 . . ?
C14 C13 H13B 110.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C11 120.2(2) . . ?
C16 C15 C20 118.8(3) . . ?
C20 C15 C11 120.8(2) . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.4(3) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C21 122.4(3) . . ?
C19 C18 C17 118.6(3) . . ?
C19 C18 C21 119.0(3) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(3) . . ?
C20 C19 H19 119.5 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.5(3) . . ?
C19 C20 H20 119.7 . . ?
O2 C21 O6 123.0(3) . . ?
O2 C21 C18 123.9(3) . . ?
O6 C21 C18 113.1(3) . . ?
O6 C22 H22A 109.5 . . ?
O6 C22 H22B 109.5 . . ?
O6 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C1 -0.6(3) . . . . ?
O1 C7 C8 C11 178.2(2) . . . . ?
O5 C9 C10 C11 178.6(3) . . . . ?
O5 C9 C10 C12 -0.7(4) . . . . ?
N1 C7 C8 C1 -179.5(3) . . . . ?
N1 C7 C8 C11 -0.8(5) . . . . ?
N1 C9 C10 C11 -0.9(5) . . . . ?
N1 C9 C10 C12 179.7(3) . . . . ?
C1 C2 C3 C4 0.7(6) . . . . ?
C1 C8 C11 C10 178.3(3) . . . . ?
C1 C8 C11 C15 -1.2(5) . . . . ?
C2 C1 C6 O1 179.1(3) . . . . ?
C2 C1 C6 C5 -1.4(5) . . . . ?
C2 C1 C8 C7 -178.8(4) . . . . ?
C2 C1 C8 C11 2.8(6) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 O1 -178.7(3) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
C6 O1 C7 N1 179.4(3) . . . . ?
C6 O1 C7 C8 0.3(3) . . . . ?
C6 C1 C2 C3 0.1(5) . . . . ?
C6 C1 C8 C7 0.6(3) . . . . ?
C6 C1 C8 C11 -177.8(3) . . . . ?
C7 O1 C6 C1 0.1(3) . . . . ?
C7 O1 C6 C5 -179.5(3) . . . . ?
C7 N1 C9 O5 -179.2(3) . . . . ?
C7 N1 C9 C10 0.4(4) . . . . ?
C7 C8 C11 C10 0.1(4) . . . . ?
C7 C8 C11 C15 -179.4(2) . . . . ?
C8 C1 C2 C3 179.4(4) . . . . ?
C8 C1 C6 O1 -0.4(3) . . . . ?
C8 C1 C6 C5 179.1(3) . . . . ?
C8 C11 C15 C16 85.9(4) . . . . ?
C8 C11 C15 C20 -90.5(4) . . . . ?
C9 N1 C7 O1 -178.3(3) . . . . ?
C9 N1 C7 C8 0.5(4) . . . . ?
C9 C10 C11 C8 0.6(4) . . . . ?
C9 C10 C11 C15 -179.9(3) . . . . ?
C9 C10 C12 O3 177.0(3) . . . . ?
C9 C10 C12 O4 -2.1(5) . . . . ?
C10 C11 C15 C16 -93.6(4) . . . . ?
C10 C11 C15 C20 90.0(4) . . . . ?
C11 C10 C12 O3 -2.3(5) . . . . ?
C11 C10 C12 O4 178.6(3) . . . . ?
C11 C15 C16 C17 -176.0(3) . . . . ?
C11 C15 C20 C19 176.2(3) . . . . ?
C12 O3 C13 C14 -179.8(5) . . . . ?
C12 C10 C11 C8 180.0(3) . . . . ?
C12 C10 C11 C15 -0.6(5) . . . . ?
C13 O3 C12 O4 6.3(5) . . . . ?
C13 O3 C12 C10 -172.8(3) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C16 C15 C20 C19 -0.2(5) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C16 C17 C18 C21 -179.9(3) . . . . ?
C17 C18 C19 C20 -0.1(5) . . . . ?
C17 C18 C21 O2 -177.9(4) . . . . ?
C17 C18 C21 O6 3.0(5) . . . . ?
C18 C19 C20 C15 0.0(5) . . . . ?
C19 C18 C21 O2 1.9(6) . . . . ?
C19 C18 C21 O6 -177.2(3) . . . . ?
C20 C15 C16 C17 0.5(5) . . . . ?
C21 C18 C19 C20 -179.9(3) . . . . ?
C22 O6 C21 O2 0.0(6) . . . . ?
C22 O6 C21 C18 179.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
