# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2106513'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-10-05 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2021-08-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N4 O2, C3 H4 O4'
_chemical_formula_sum            'C10 H12 N4 O6'
_chemical_formula_weight         284.24
_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 -0.0019 0.0002 '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 -0.0030 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O -0.0036 0.0009 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   17.1509(5)
_cell_length_b                   8.3690(2)
_cell_length_c                   17.4870(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.949(8)
_cell_angle_gamma                90
_cell_volume                     2400.99(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10197
_cell_measurement_temperature    20(0)
_cell_measurement_theta_max      18.052
_cell_measurement_theta_min      1.061
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.037
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9839
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        10.715
_diffrn_reflns_theta_max         18.052
_diffrn_reflns_theta_min         1.061
_diffrn_ambient_temperature      20(0)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'BL02B1 beamline'
_diffrn_measurement_method       ?
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.30988
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7942
_reflns_number_total             9839
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         9839
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C1-H1A
 1.083 with sigma of 0.2
 N1-H1
 1.009 with sigma of 0.2
 C7-H7A
 1.059 with sigma of 0.2
 C7-H7B
 1.059 with sigma of 0.2
 C7-H7C
 1.059 with sigma of 0.2
 C6-H6A
 1.059 with sigma of 0.2
 C6-H6B
 1.059 with sigma of 0.2
 C6-H6C
 1.059 with sigma of 0.2
 C02-H02A
 1.092 with sigma of 0.2
 C02-H02B
 1.092 with sigma of 0.2
 O01-H01
 1.015 with sigma of 0.2
 O04-H04
 1.015 with sigma of 0.2
;
_atom_sites_solution_hydrogens   difmap
_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 0.51456(2) 0.09071(4) 0.64171(2) 0.00906(4) Uani 1 1 d . . . . .
O2 O 0.68360(2) -0.27065(4) 0.57372(2) 0.01151(5) Uani 1 1 d . . . . .
O01 O 0.70308(2) 0.89747(4) 0.26776(2) 0.00990(5) Uani 1 1 d D . . . .
O02 O 0.69226(2) 0.67342(4) 0.19460(2) 0.01165(5) Uani 1 1 d . . . . .
O03 O 0.69950(2) 0.45689(4) 0.32769(2) 0.01031(5) Uani 1 1 d . . . . .
O04 O 0.59548(2) 0.49855(4) 0.37740(2) 0.01211(5) Uani 1 1 d D . . . .
N1 N 0.70641(2) -0.01634(4) 0.45488(2) 0.00821(5) Uani 1 1 d D . . . .
N2 N 0.64169(2) 0.21736(4) 0.44432(2) 0.00783(5) Uani 1 1 d . . . . .
N3 N 0.57023(2) 0.16556(4) 0.54356(2) 0.00706(4) Uani 1 1 d . . . . .
N4 N 0.59837(2) -0.08851(4) 0.60623(2) 0.00696(4) Uani 1 1 d . . . . .
C1 C 0.69331(2) 0.12622(5) 0.41840(2) 0.00852(5) Uani 1 1 d D . . . .
C2 C 0.62193(2) 0.12546(4) 0.50014(2) 0.00656(5) Uani 1 1 d . . . . .
C3 C 0.55819(2) 0.05942(4) 0.59956(2) 0.00662(5) Uani 1 1 d . . . . .
C4 C 0.65111(2) -0.13754(4) 0.56300(2) 0.00724(5) Uani 1 1 d . . . . .
C5 C 0.66087(2) -0.01959(4) 0.50813(2) 0.00705(5) Uani 1 1 d . . . . .
C6 C 0.53554(3) 0.32612(5) 0.53727(2) 0.00982(5) Uani 1 1 d D . . . .
C7 C 0.58514(3) -0.19627(5) 0.66772(2) 0.00960(5) Uani 1 1 d D . . . .
C01 C 0.67478(2) 0.75193(5) 0.24556(2) 0.00813(5) Uani 1 1 d . . . . .
C02 C 0.61603(3) 0.69399(5) 0.28880(3) 0.01062(6) Uani 1 1 d D . . . .
C03 C 0.64219(2) 0.53859(4) 0.33273(2) 0.00720(5) Uani 1 1 d . . . . .
H1A H 0.7189(6) 0.1570(11) 0.3800(6) 0.014(2) Uiso 1 1 d D . . . .
H1 H 0.7421(7) -0.0967(14) 0.4466(6) 0.024(3) Uiso 1 1 d D . . . .
H6A H 0.5773(7) 0.4030(13) 0.5590(7) 0.025(3) Uiso 1 1 d D . . . .
H6B H 0.4976(7) 0.3294(13) 0.5675(6) 0.022(2) Uiso 1 1 d D . . . .
H6C H 0.5092(7) 0.3490(13) 0.4821(6) 0.021(2) Uiso 1 1 d D . . . .
H7A H 0.6124(7) -0.2946(14) 0.6621(7) 0.028(3) Uiso 1 1 d D . . . .
H7B H 0.5277(7) -0.2108(13) 0.6593(6) 0.021(2) Uiso 1 1 d D . . . .
H7C H 0.6082(6) -0.1519(13) 0.7204(6) 0.020(2) Uiso 1 1 d D . . . .
H01 H 0.7380(8) 0.9265(16) 0.2394(8) 0.042(4) Uiso 1 1 d D . . . .
H02A H 0.5665(7) 0.6698(13) 0.2475(6) 0.024(3) Uiso 1 1 d D . . . .
H02B H 0.6060(8) 0.7756(15) 0.3256(7) 0.031(3) Uiso 1 1 d D . . . .
H04 H 0.6106(9) 0.3994(17) 0.4029(9) 0.049(4) Uiso 1 1 d 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
O1 C3 1.2221(5) . ?
O2 C4 1.2352(5) . ?
O01 C01 1.3267(5) . ?
O01 H01 0.915(15) . ?
O02 C01 1.2131(5) . ?
O03 C03 1.2214(5) . ?
O04 C03 1.3150(5) . ?
O04 H04 0.942(14) . ?
N1 C1 1.3407(5) . ?
N1 C5 1.3791(5) . ?
N1 H1 0.949(11) . ?
N2 C1 1.3435(5) . ?
N2 C2 1.3609(5) . ?
N3 C2 1.3667(5) . ?
N3 C3 1.3815(5) . ?
N3 C6 1.4607(5) . ?
N4 C3 1.4050(5) . ?
N4 C4 1.3989(5) . ?
N4 C7 1.4708(5) . ?
C1 H1A 0.939(10) . ?
C2 C5 1.3729(5) . ?
C4 C5 1.4200(5) . ?
C6 H6A 0.955(11) . ?
C6 H6B 0.951(11) . ?
C6 H6C 0.958(11) . ?
C7 H7A 0.966(12) . ?
C7 H7B 0.960(11) . ?
C7 H7C 0.964(10) . ?
C01 C02 1.5053(6) . ?
C02 C03 1.5105(5) . ?
C02 H02A 0.962(11) . ?
C02 H02B 0.987(13) . ?

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
C01 O01 H01 109.1(8) . . ?
C03 O04 H04 112.0(9) . . ?
C1 N1 C5 106.83(3) . . ?
C1 N1 H1 125.7(7) . . ?
C5 N1 H1 127.4(7) . . ?
C1 N2 C2 104.33(3) . . ?
C2 N3 C3 119.42(3) . . ?
C2 N3 C6 120.00(3) . . ?
C3 N3 C6 120.21(3) . . ?
C3 N4 C7 115.12(3) . . ?
C4 N4 C3 126.32(3) . . ?
C4 N4 C7 118.50(3) . . ?
N1 C1 N2 112.34(3) . . ?
N1 C1 H1A 122.4(6) . . ?
N2 C1 H1A 125.2(6) . . ?
N2 C2 N3 126.68(3) . . ?
N2 C2 C5 110.93(3) . . ?
N3 C2 C5 122.39(3) . . ?
O1 C3 N3 122.28(3) . . ?
O1 C3 N4 120.69(3) . . ?
N3 C3 N4 117.03(3) . . ?
O2 C4 N4 121.11(3) . . ?
O2 C4 C5 126.34(4) . . ?
N4 C4 C5 112.55(3) . . ?
N1 C5 C4 132.18(3) . . ?
C2 C5 N1 105.56(3) . . ?
C2 C5 C4 122.26(3) . . ?
N3 C6 H6A 110.3(7) . . ?
N3 C6 H6B 108.4(7) . . ?
N3 C6 H6C 108.8(7) . . ?
H6A C6 H6B 108.3(9) . . ?
H6A C6 H6C 110.2(9) . . ?
H6B C6 H6C 110.8(9) . . ?
N4 C7 H7A 105.4(7) . . ?
N4 C7 H7B 109.6(6) . . ?
N4 C7 H7C 110.7(7) . . ?
H7A C7 H7B 112.5(10) . . ?
H7A C7 H7C 110.4(9) . . ?
H7B C7 H7C 108.2(9) . . ?
O01 C01 C02 112.97(3) . . ?
O02 C01 O01 124.36(4) . . ?
O02 C01 C02 122.65(4) . . ?
C01 C02 C03 112.94(3) . . ?
C01 C02 H02A 105.4(7) . . ?
C01 C02 H02B 111.9(7) . . ?
C03 C02 H02A 105.5(7) . . ?
C03 C02 H02B 110.3(7) . . ?
H02A C02 H02B 110.5(10) . . ?
O03 C03 O04 122.87(4) . . ?
O03 C03 C02 124.83(4) . . ?
O04 C03 C02 112.30(3) . . ?

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 C4 C5 N1 -0.74(7) . . . . ?
O2 C4 C5 C2 179.79(4) . . . . ?
O01 C01 C02 C03 -122.89(4) . . . . ?
O02 C01 C02 C03 58.66(5) . . . . ?
N2 C2 C5 N1 -0.03(4) . . . . ?
N2 C2 C5 C4 179.56(3) . . . . ?
N3 C2 C5 N1 179.48(3) . . . . ?
N3 C2 C5 C4 -0.93(6) . . . . ?
N4 C4 C5 N1 179.56(4) . . . . ?
N4 C4 C5 C2 0.10(5) . . . . ?
C1 N1 C5 C2 0.07(4) . . . . ?
C1 N1 C5 C4 -179.46(4) . . . . ?
C1 N2 C2 N3 -179.51(4) . . . . ?
C1 N2 C2 C5 -0.02(4) . . . . ?
C2 N2 C1 N1 0.07(4) . . . . ?
C2 N3 C3 O1 177.83(3) . . . . ?
C2 N3 C3 N4 -2.38(5) . . . . ?
C3 N3 C2 N2 -178.45(3) . . . . ?
C3 N3 C2 C5 2.12(5) . . . . ?
C3 N4 C4 O2 179.76(4) . . . . ?
C3 N4 C4 C5 -0.53(5) . . . . ?
C4 N4 C3 O1 -178.52(3) . . . . ?
C4 N4 C3 N3 1.69(5) . . . . ?
C5 N1 C1 N2 -0.09(5) . . . . ?
C6 N3 C2 N2 -5.44(6) . . . . ?
C6 N3 C2 C5 175.13(4) . . . . ?
C6 N3 C3 O1 4.83(5) . . . . ?
C6 N3 C3 N4 -175.38(3) . . . . ?
C7 N4 C3 O1 -1.43(5) . . . . ?
C7 N4 C3 N3 178.78(3) . . . . ?
C7 N4 C4 O2 2.76(5) . . . . ?
C7 N4 C4 C5 -177.53(3) . . . . ?
C01 C02 C03 O03 -7.74(6) . . . . ?
C01 C02 C03 O04 172.86(4) . . . . ?

_olex2_exptl_crystal_mounting_method ?
_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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2119969'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2021-11-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H8 N4 O2'
_chemical_formula_sum            'C7 H8 N4 O2'
_chemical_formula_weight         180.17
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   24.3625(2)
_cell_length_b                   3.77810(10)
_cell_length_c                   8.47980(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     780.51(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    54614
_cell_measurement_temperature    150(0)
_cell_measurement_theta_max      63.806
_cell_measurement_theta_min      4.064
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.449
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
        CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
        implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.533
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 1 -12 0.1887
-29 1 -6 0.1587
-19 4 -4 0.3196
29 0 6 0.1567
-34 0 1 0.1181
-29 3 0 0.2541
34 0 -1 0.118
17 0 -10 0.1853
7 0 -12 0.1864
-8 0 12 0.1788
-4 0 -12 0.1842
3 0 12 0.1812
-23 0 -9 0.1774
23 1 9 0.17
-33 0 -3 0.1273
33 0 3 0.1254
-34 0 1 0.1256
6 -5 2 0.3737
34 1 -1 0.1246
-2 5 -4 0.3952
-17 0 10 0.1807
6 1 -12 0.1849
-7 0 12 0.1852

_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            8913
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         52.123
_diffrn_reflns_theta_min         4.119
_diffrn_ambient_temperature      150(0)
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                8396
_reflns_number_total             8913
_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 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 3642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.298
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         8913
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.303
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.0885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C6-H6A
 1.059 with sigma of 0.02
 C6-H6B
 1.059 with sigma of 0.02
 C6-H6C
 1.059 with sigma of 0.02
 C7-H7A
 1.059 with sigma of 0.02
 C7-H7B
 1.059 with sigma of 0.02
 C7-H7C
 1.059 with sigma of 0.02
 C1-H1
 1.083 with sigma of 0.02
 N1-H1A
 1.009 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_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
C1 C 0.75083(3) 0.3039(3) 0.58705(10) 0.01780(12) Uani 1 1 d D . . . .
C2 C 0.67020(3) 0.5174(2) 0.59864(9) 0.01358(9) Uani 1 1 d . . . . .
C3 C 0.58135(4) 0.7357(3) 0.53829(13) 0.01944(14) Uani 1 1 d . . . . .
C4 C 0.63685(3) 0.4414(2) 0.32726(9) 0.01473(10) Uani 1 1 d . . . . .
C5 C 0.67763(3) 0.4022(2) 0.44648(9) 0.01316(9) Uani 1 1 d . . . . .
C6 C 0.61572(6) 0.7895(3) 0.81109(14) 0.0265(2) Uani 1 1 d D . . . .
C7 C 0.54557(5) 0.6787(4) 0.2709(2) 0.0309(3) Uani 1 1 d D . . . .
N1 N 0.73007(3) 0.2653(2) 0.44201(8) 0.01506(9) Uani 1 1 d D . . . .
N2 N 0.71562(3) 0.4570(2) 0.68778(9) 0.01760(11) Uani 1 1 d . . . . .
N3 N 0.62250(3) 0.6738(2) 0.64756(10) 0.01769(11) Uani 1 1 d . . . . .
N4 N 0.58992(3) 0.6124(2) 0.38424(10) 0.01839(12) Uani 1 1 d . . . . .
O2 O 0.64117(3) 0.3438(3) 0.18902(9) 0.02178(13) Uani 1 1 d . . . . .
O1 O 0.53948(4) 0.8948(3) 0.57406(16) 0.0319(2) Uani 1 1 d . . . . .
H6A H 0.6163(16) 0.586(8) 0.883(4) 0.070(11) Uiso 1 1 d D . . . .
H6B H 0.5800(12) 0.923(10) 0.824(5) 0.075(12) Uiso 1 1 d D . . . .
H6C H 0.6436(11) 0.981(7) 0.834(4) 0.046(8) Uiso 1 1 d D . . . .
H1A H 0.7494(11) 0.154(8) 0.354(3) 0.045(8) Uiso 1 1 d D . . . .
H7A H 0.5526(13) 0.915(7) 0.221(4) 0.051(9) Uiso 1 1 d D . . . .
H7B H 0.5111(14) 0.737(13) 0.324(6) 0.102(17) Uiso 1 1 d D . . . .
H7C H 0.5421(15) 0.460(8) 0.207(5) 0.075(12) Uiso 1 1 d D . . . .
H1 H 0.7897(9) 0.211(7) 0.608(4) 0.033(6) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.3378(10) . ?
C1 N2 1.3416(11) . ?
C1 H1 1.03(2) . ?
C2 C5 1.3738(10) . ?
C2 N2 1.3594(11) . ?
C2 N3 1.3680(10) . ?
C3 N3 1.3850(14) . ?
C3 N4 1.4025(14) . ?
C3 O1 1.2221(12) . ?
C4 C5 1.4251(10) . ?
C4 N4 1.3994(11) . ?
C4 O2 1.2333(11) . ?
C5 N1 1.3789(10) . ?
C6 N3 1.4634(13) . ?
C6 H6A 0.98(2) . ?
C6 H6B 1.01(2) . ?
C6 H6C 1.01(2) . ?
C7 N4 1.4677(14) . ?
C7 H7A 1.00(2) . ?
C7 H7B 0.98(2) . ?
C7 H7C 0.99(2) . ?
N1 H1A 0.98(2) . ?

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
N1 C1 N2 113.00(7) . . ?
N1 C1 H1 118.0(17) . . ?
N2 C1 H1 129.0(17) . . ?
N2 C2 C5 111.21(6) . . ?
N2 C2 N3 126.54(7) . . ?
N3 C2 C5 122.25(7) . . ?
N3 C3 N4 117.35(7) . . ?
O1 C3 N3 121.40(11) . . ?
O1 C3 N4 121.24(11) . . ?
N4 C4 C5 111.88(7) . . ?
O2 C4 C5 125.71(8) . . ?
O2 C4 N4 122.41(8) . . ?
C2 C5 C4 122.78(7) . . ?
C2 C5 N1 105.48(6) . . ?
N1 C5 C4 131.72(7) . . ?
N3 C6 H6A 111(2) . . ?
N3 C6 H6B 110(3) . . ?
N3 C6 H6C 109(2) . . ?
H6A C6 H6B 110(3) . . ?
H6A C6 H6C 116(3) . . ?
H6B C6 H6C 101(3) . . ?
N4 C7 H7A 108(2) . . ?
N4 C7 H7B 112(3) . . ?
N4 C7 H7C 106(2) . . ?
H7A C7 H7B 98(4) . . ?
H7A C7 H7C 122(3) . . ?
H7B C7 H7C 112(4) . . ?
C1 N1 C5 106.50(6) . . ?
C1 N1 H1A 124.3(19) . . ?
C5 N1 H1A 129.1(18) . . ?
C1 N2 C2 103.82(6) . . ?
C2 N3 C3 119.01(8) . . ?
C2 N3 C6 120.81(9) . . ?
C3 N3 C6 120.12(9) . . ?
C3 N4 C7 116.35(9) . . ?
C4 N4 C3 126.62(7) . . ?
C4 N4 C7 117.00(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A N2 0.98(2) 1.81(2) 2.7848(10) 178(3) 4_644 yes

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
C2 C5 N1 C1 0.00(10) . . . . ?
C4 C5 N1 C1 178.11(9) . . . . ?
C5 C2 N2 C1 0.16(11) . . . . ?
C5 C2 N3 C3 -3.55(13) . . . . ?
C5 C2 N3 C6 179.24(9) . . . . ?
C5 C4 N4 C3 -0.20(13) . . . . ?
C5 C4 N4 C7 178.10(10) . . . . ?
N1 C1 N2 C2 -0.16(12) . . . . ?
N2 C1 N1 C5 0.10(12) . . . . ?
N2 C2 C5 C4 -178.42(8) . . . . ?
N2 C2 C5 N1 -0.10(10) . . . . ?
N2 C2 N3 C3 175.88(9) . . . . ?
N2 C2 N3 C6 -1.34(15) . . . . ?
N3 C2 C5 C4 1.08(13) . . . . ?
N3 C2 C5 N1 179.40(8) . . . . ?
N3 C2 N2 C1 -179.32(9) . . . . ?
N3 C3 N4 C4 -2.15(14) . . . . ?
N3 C3 N4 C7 179.54(10) . . . . ?
N4 C3 N3 C2 3.92(13) . . . . ?
N4 C3 N3 C6 -178.84(9) . . . . ?
N4 C4 C5 C2 0.78(11) . . . . ?
N4 C4 C5 N1 -177.05(9) . . . . ?
O2 C4 C5 C2 179.93(9) . . . . ?
O2 C4 C5 N1 2.09(16) . . . . ?
O2 C4 N4 C3 -179.38(9) . . . . ?
O2 C4 N4 C7 -1.08(14) . . . . ?
O1 C3 N3 C2 -175.27(10) . . . . ?
O1 C3 N3 C6 1.96(15) . . . . ?
O1 C3 N4 C4 177.05(10) . . . . ?
O1 C3 N4 C7 -1.27(16) . . . . ?

_olex2_submission_original_sample_id 'THEO AN FOrm II'
_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_16jd001
_database_code_depnum_ccdc_archive 'CCDC 2119968'
loop_
_audit_author_name
_audit_author_address
'Bryson Hawkins'
;Sydney School of Pharmacy, Faculty of Medicine and Health, The University of Sydney 
Australia
;
_audit_update_record             
;
2021-11-03 deposited with the CCDC.	2022-02-16 downloaded from the CCDC.
;
_audit_creation_date             2021-11-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
loop_
_audit_author_email
bryson.hawkins@sydney.edu.au
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H4 O4'
_chemical_formula_sum            'C3 H4 O4'
_chemical_formula_weight         103.98
_chemical_melting_point          ?
_chemical_oxdiff_formula         C3H4O4
_chemical_oxdiff_usercomment     'Malonic Acid'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.15560(10)
_cell_length_b                   5.32510(10)
_cell_length_c                   8.19420(10)
_cell_angle_alpha                108.1080(10)
_cell_angle_beta                 101.2440(10)
_cell_angle_gamma                95.2650(10)
_cell_volume                     206.898(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    53972
_cell_measurement_temperature    149.9(5)
_cell_measurement_theta_max      65.4590
_cell_measurement_theta_min      4.0460
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.161
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.213
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             108
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -1 -9 0.2612
6 1 1 0.1895
-1 7 1 0.3003
-7 -2 3 0.2297
5 -6 3 0.3016
-5 5 5 0.3164
7 1 -2 0.2076
4 -7 0 0.3308
7 0 -1 0.1955
1 -5 10 0.3025
-6 -1 -2 0.1723
-1 7 -5 0.3426
3 -5 9 0.2875
-7 0 5 0.2082
-1 -2 11 0.2913
1 -1 -11 0.2607
-3 -2 -7 0.2154
-6 0 7 0.2377
-6 -1 8 0.2344
6 0 -8 0.2431
1 -7 5 0.3884
1 -1 10 0.2807
-1 -2 -9 0.2312
-5 3 -7 0.3095
-6 -2 -1 0.1797
-2 -3 11 0.2939
6 -2 3 0.2151
0 7 1 0.2881
4 5 1 0.2629
-2 7 -5 0.3444
5 -4 7 0.2639
2 6 1 0.2781
-1 -1 -9 0.2442
7 0 -4 0.2132
-7 0 1 0.1836
-5 -2 -4 0.1977

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.74
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.36
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
5.0333 -1.0139 -8.9455 -0.4291 -0.9013 0.0600
6.3977 1.2506 1.3854 0.7226 -0.6847 -0.0948
-1.2095 6.8869 1.0759 0.4427 0.2420 -0.8634
-6.6273 -2.3838 2.7413 -0.4584 0.8422 0.2839
4.9139 -5.8221 3.0451 0.2848 -0.5215 0.8043
-4.6216 4.5838 5.0454 0.3578 0.7532 -0.5520
7.0473 0.9768 -1.8770 0.4757 -0.8746 -0.0936
4.0324 -6.5065 0.3242 -0.0668 -0.5187 0.8523
7.1916 -0.1515 -1.1489 0.4770 -0.8770 0.0580
1.4971 -4.6260 10.0730 0.6918 0.1278 0.7107
-6.4485 -0.9682 -1.5729 -0.7246 0.6868 0.0567
-0.8792 7.4410 -4.8606 -0.0075 0.0054 -1.0000
2.9822 -4.6717 8.7604 0.6963 -0.0903 0.7120
-7.0983 -0.0546 4.6184 -0.1829 0.9831 0.0091
-0.6626 -1.5067 11.3925 0.8328 0.4533 0.3177
0.9535 -0.7400 -10.5010 -0.8783 -0.4776 -0.0223
-3.2123 -2.2343 -6.5684 -0.9751 0.1275 0.1814
-6.3678 0.3734 7.2250 0.1299 0.9915 -0.0091
-6.1497 -0.8813 7.9428 0.1280 0.9790 0.1588
6.3019 0.1294 -7.5381 -0.1296 -0.9899 -0.0583
0.8268 -7.4383 4.9225 0.0088 0.0029 1.0000
1.4443 -0.7947 10.3028 0.9567 0.1777 0.2306
-1.1358 -2.1371 -8.5429 -0.9702 -0.1807 0.1613
-4.8852 3.2354 -6.7385 -0.7702 0.3674 -0.5214
-6.2809 -1.7637 -1.0333 -0.7161 0.6784 0.1644
-2.4485 -2.6084 11.3996 0.6162 0.6509 0.4435
6.4565 -1.6821 3.2016 0.6936 -0.6568 0.2960
-0.0425 6.8556 0.7862 0.5107 0.0961 -0.8544
3.7757 4.9291 1.2502 0.7367 -0.3500 -0.5786
-1.6312 7.3659 -4.6498 -0.0555 0.0993 -0.9935
4.6023 -4.0369 6.8751 0.7067 -0.3373 0.6219
1.5884 6.2469 1.2482 0.6440 -0.0834 -0.7605
-1.2944 -0.8815 -9.4876 -0.9831 -0.1829 -0.0090
7.1223 -0.1744 -4.4686 0.1829 -0.9829 0.0217
-7.1482 -0.3485 1.4762 -0.4777 0.8785 0.0091
-4.9496 -2.2225 -3.8971 -0.8850 0.4212 0.1985

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.026
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            3476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         45.294
_diffrn_reflns_theta_min         4.063
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2474
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 150.00  109
  2  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00  60.00  109
  3  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-120.00  109
  4  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 -30.00  109
  5  ω    -31.00  70.00   1.00    5.93    --   41.57 -57.00-180.00  101
  6  ω     13.00 114.00   1.00    5.93    --   41.57  57.00-150.00  101
  7  ω     13.00 114.00   1.00    5.93    --   41.57  57.00 -30.00  101
  8  ω     13.00 114.00   1.00    5.93    --   41.57  57.00 120.00  101
  9  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00  30.00  109
 10  ω     62.00 158.00   1.00   35.00    --   90.50  59.00  29.18   96
 11  ω     64.00 158.00   1.00   35.00    --   90.50  50.00-169.21   94
 12  ω     62.00 158.00   1.00   35.00    --   90.50  57.00 -91.18   96
 13  ω     62.00 158.00   1.00   35.00    --   90.50  60.00 -20.94   96
 14  ω     62.00 158.00   1.00   35.00    --   90.50  60.00 136.33   96
 15  ω     63.00 158.00   1.00   35.00    --   90.50  56.00  58.10   95
 16  ω     13.00 124.00   1.00   35.00    --   90.50 -80.00 -78.01  111
 17  ω     62.00 158.00   1.00   35.00    --   90.50  57.00 115.81   96
 18  ω     13.00 124.00   1.00   35.00    --   90.50 -80.00 165.81  111
 19  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00  11.62  110
 20  ω     63.00 158.00   1.00   35.00    --   90.50  56.00 -37.04   95
 21  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00  93.92  110
 22  ω     62.00 158.00   1.00   35.00    --   90.50  57.00 151.35   96
 23  ω     62.00 158.00   1.00   35.00    --   90.50  60.00  91.21   96
 24  ω     62.00 158.00   1.00   35.00    --   90.50  57.00 -50.85   96
 25  ω     63.00 158.00   1.00   35.00    --   90.50  56.00 -75.71   95
 26  ω     64.00 158.00   1.00   35.00    --   90.50  47.00  18.20   94
 27  ω     65.00 158.00   1.00   35.00    --   90.50  45.00-150.00   93
 28  ω     17.00  77.00   1.00   35.00    --   90.50 -45.00 -90.00   60
 29  ω     17.00  77.00   1.00   35.00    --   90.50 -45.00-180.00   60
 30  ω     65.00 158.00   1.00   35.00    --   90.50  45.00-120.00   93
 31  ω     62.00 158.00   1.00   35.00    --   90.50  57.00-119.31   96
 32  ω     17.00  77.00   1.00   35.00    --   90.50 -45.00   0.00   60
 33  ω     62.00 158.00   1.00   35.00    --   90.50  58.00  81.17   96
 34  ω   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00   0.00  101
 35  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00   0.00  109
 36  ω   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00-180.00  101
 37  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00 120.00  109
 38  ω   -114.00 -13.00   1.00    5.93    --  -41.57 -57.00-120.00  101
 39  ω   -115.00 -16.00   1.00    5.93    --  -41.57 -41.00  65.86   99
 40  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -60.00  109
 41  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00-120.00  109
 42  ω    -31.00  70.00   1.00    5.93    --   41.57 -57.00-150.00  101
 43  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -90.00  109
 44  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00-150.00  109
 45  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00-180.00  109
 46  ω     17.00  77.00   1.00   35.00    --   90.50 -45.00  60.00   60
 47  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00  93.92  110
 48  ω     63.00 158.00   1.00   35.00    --   90.50  56.00-104.06   95
 49  ω     65.00 158.00   1.00   35.00    --   90.50  45.00-180.00   93
 50  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00 -60.00  109
 51  ω     63.00 158.00   1.00   35.00    --   90.50  52.00 -26.01   95
 52  ω     13.00 124.00   1.00   35.00    --   90.50 -80.00  39.67  111
 53  ω     62.00 158.00   1.00   35.00    --   90.50  59.00 101.61   96
 54  ω     65.00 158.00   1.00   35.00    --   90.50  45.00  90.00   93
 55  ω     65.00 158.00   1.00   35.00    --   90.50  45.00 150.00   93
 56  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00 122.30  110
 57  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00  30.00  109
 58  ω     13.00 124.00   1.00   35.00    --   90.50 -80.00 -78.01  111
 59  ω     13.00 124.00   1.00   35.00    --   90.50 -80.00 165.81  111
 60  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00-120.00  109
 61  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00 134.50  110
 62  ω     13.00 123.00   1.00   35.00    --   90.50 -79.00  11.62  110
 63  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00-180.00  109
 64  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00   0.00  109
 65  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00 -30.00  109
 66  ω     65.00 158.00   1.00   35.00    --   90.50  45.00  30.00   93
 67  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00 -90.00  109
 68  ω     14.00 123.00   1.00   35.00    --   90.50 -77.00-150.00  109
 69  ω     63.00 158.00   1.00   35.00    --   90.50  53.00  54.77   95
 70  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-180.00  109
 71  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-150.00  109
 72  ω   -118.00  -9.00   1.00    5.93    --  -41.57 -77.00-120.00  109
 73  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00  30.00  109
 74  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00 120.00  109
 75  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00 150.00  109
 76  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00  90.00  109
 77  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00  60.00  109
 78  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00   0.00  109
 79  ω    -35.00  74.00   1.00    5.93    --   41.57 -77.00 -30.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0815093000
_diffrn_orient_matrix_UB_12      0.0650888000
_diffrn_orient_matrix_UB_13      0.0864512000
_diffrn_orient_matrix_UB_21      -0.1162741000
_diffrn_orient_matrix_UB_22      0.0093654000
_diffrn_orient_matrix_UB_23      0.0342670000
_diffrn_orient_matrix_UB_31      0.0072683000
_diffrn_orient_matrix_UB_32      -0.1259137000
_diffrn_orient_matrix_UB_33      0.0116535000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_number_gt                3302
_reflns_number_total             3476
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     45.18
_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 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.118a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.043
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       0.35(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     77
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0553P)²+0.0378P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1143
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O01-H01
 1.015 with sigma of 0.02
 O04-H04
 1.015 with sigma of 0.02
 H02A-C02
 1.098 with sigma of 0.002
 H02B-C02
 1.098 with sigma of 0.002
;
_atom_sites_solution_hydrogens   difmap
_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
O03 O 0.45613(7) 0.30754(7) 0.12485(5) 0.01670(7) Uani 1 1 d . . . . .
O04 O 0.83266(8) 0.17720(7) 0.05224(6) 0.02011(8) Uani 1 1 d D . . . .
H04 H 0.716(3) 0.018(2) -0.0215(17) 0.030 Uiso 1 1 d D U . . .
O01 O 0.73213(11) 0.75643(11) 0.51937(6) 0.02757(10) Uani 1 1 d D . . . .
H01 H 0.619(3) 0.857(3) 0.5770(19) 0.041 Uiso 1 1 d D U . . .
O02 O 0.58400(12) 0.93690(10) 0.31401(7) 0.02803(11) Uani 1 1 d . . . . .
C01 C 0.71638(9) 0.78549(8) 0.36505(6) 0.01480(7) Uani 1 1 d . . . . .
C03 C 0.69806(8) 0.34853(8) 0.13654(5) 0.01323(7) Uani 1 1 d . . . . .
C02 C 0.87358(9) 0.61042(9) 0.25320(6) 0.01630(7) Uani 1 1 d D . . . .
H02A H 1.0440(15) 0.565(2) 0.3359(13) 0.020 Uiso 1 1 d D U . . .
H02B H 0.936(2) 0.711(2) 0.1659(12) 0.020 Uiso 1 1 d D 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
O03 C03 1.2259(5) . ?
O04 H04 0.945(11) . ?
O04 C03 1.3048(5) . ?
O01 H01 0.924(13) . ?
O01 C01 1.3090(6) . ?
O02 C01 1.2207(6) . ?
C01 C02 1.5044(6) . ?
C03 C02 1.5099(6) . ?
C02 H02A 1.095(2) . ?
C02 H02B 1.095(2) . ?

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
C03 O04 H04 110.2(8) . . ?
C01 O01 H01 109.5(10) . . ?
O01 C01 C02 113.76(4) . . ?
O02 C01 O01 123.71(4) . . ?
O02 C01 C02 122.52(4) . . ?
O03 C03 O04 125.10(4) . . ?
O03 C03 C02 122.37(4) . . ?
O04 C03 C02 112.52(4) . . ?
C01 C02 C03 110.20(3) . . ?
C01 C02 H02A 110.9(6) . . ?
C01 C02 H02B 108.3(6) . . ?
C03 C02 H02A 107.9(6) . . ?
C03 C02 H02B 107.1(6) . . ?
H02A C02 H02B 112.4(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
O03 C03 C02 C01 7.70(6) . . . . ?
O04 C03 C02 C01 -172.41(4) . . . . ?
O01 C01 C02 C03 91.81(5) . . . . ?
O02 C01 C02 C03 -87.17(6) . . . . ?


_ins_header                      
;
TITL 16JD001 in P-1 
REM P-1 (#2 in standard setting)
CELL 0.71073   5.155569   5.325063   8.194224 108.1076 101.2440  95.2653
ZERR    2.00   0.000064   0.000070   0.000098   0.0011   0.0010   0.0010
LATT  1
SFAC C H O
UNIT 6.00 8.00 8.00
REM  CrysAlisPro recorded range (K): Min=149.6; max=150.3; aver:149.9
TEMP -123
SIZE 0.36 0.62 0.74
TREF
HKLF 4
END
;
_olex2_exptl_crystal_mounting_method Paratone-N
_olex2_submission_original_sample_id 'THEO AN II'
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.772
