# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2322035'
loop_
_audit_author_name
_audit_author_address
'jiang zhouyu'
;Southeast university
China
;
_audit_update_record             
;
2023-12-27 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 N4 O5'
_chemical_formula_weight         257.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   10.9806(11)
_cell_length_b                   4.9204(5)
_cell_length_c                   22.904(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.980(3)
_cell_angle_gamma                90
_cell_volume                     1235.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4039
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      24.48

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.114
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ccd
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17385
_diffrn_reflns_av_unetI/netI     0.0497
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.174
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2158
_reflns_number_gt                1408
_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    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0437P)²+0.4698P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2158
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1157
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6746(3) 0.4704(7) 0.33296(14) 0.0832(10) Uani 1 1 d . . . . .
H1A H 0.6920 0.5429 0.3714 0.125 Uiso 1 1 calc R U . . .
H1B H 0.7496 0.4392 0.3143 0.125 Uiso 1 1 calc R U . . .
H1C H 0.6312 0.3020 0.3358 0.125 Uiso 1 1 calc R U . . .
C2 C 0.4607(2) 1.0081(5) 0.24415(13) 0.0522(7) Uani 1 1 d . . . . .
C3 C 0.4277(2) 0.8847(5) 0.29788(10) 0.0420(6) Uani 1 1 d . . . . .
C4 C 0.3117(2) 0.9743(5) 0.32229(10) 0.0431(6) Uani 1 1 d . . . . .
C5 C 0.18015(19) 0.8958(5) 0.40534(10) 0.0397(6) Uani 1 1 d . . . . .
C6 C 0.0075(2) 1.1874(5) 0.42328(11) 0.0516(7) Uani 1 1 d . . . . .
H6A H -0.0067 1.3804 0.4176 0.062 Uiso 1 1 calc R U . . .
H6B H 0.0271 1.1571 0.4646 0.062 Uiso 1 1 calc R U . . .
C7 C -0.1063(2) 1.0359(6) 0.40566(13) 0.0696(8) Uani 1 1 d . . . . .
H7A H -0.1240 1.0581 0.3645 0.104 Uiso 1 1 calc R U . . .
H7B H -0.1728 1.1056 0.4268 0.104 Uiso 1 1 calc R U . . .
H7C H -0.0952 0.8464 0.4144 0.104 Uiso 1 1 calc R U . . .
C8 C 0.3820(2) 0.2787(5) 0.48057(11) 0.0430(6) Uani 1 1 d . . . . .
C9 C 0.4468(2) 0.0594(5) 0.51490(10) 0.0481(6) Uani 1 1 d . . . . .
H9A H 0.3893 -0.0847 0.5222 0.058 Uiso 1 1 calc R U . . .
H9B H 0.4756 0.1327 0.5524 0.058 Uiso 1 1 calc R U . . .
N1 N 0.49566(17) 0.7135(4) 0.32584(9) 0.0506(6) Uani 1 1 d . . . . .
N2 N 0.4905(2) 1.1008(6) 0.20198(11) 0.0803(8) Uani 1 1 d . . . . .
N3 N 0.27680(16) 0.8326(4) 0.36955(8) 0.0427(5) Uani 1 1 d . . . . .
H3 H 0.3182 0.6888 0.3786 0.051 Uiso 1 1 calc R U . . .
N4 N 0.11117(16) 1.1053(4) 0.39012(8) 0.0455(5) Uani 1 1 d . . . . .
H4 H 0.1278 1.1969 0.3596 0.055 Uiso 1 1 calc R U . . .
O1 O 0.60105(15) 0.6613(4) 0.29893(8) 0.0678(6) Uani 1 1 d . . . . .
O2 O 0.25761(15) 1.1671(4) 0.30017(7) 0.0593(5) Uani 1 1 d . . . . .
O3 O 0.16653(14) 0.7557(3) 0.44901(7) 0.0535(5) Uani 1 1 d . . . . .
O4 O 0.40916(15) 0.3560(3) 0.43298(8) 0.0589(5) Uani 1 1 d . . . . .
O5 O 0.28921(15) 0.3807(3) 0.50775(7) 0.0594(5) Uani 1 1 d . . . . .
H5O H 0.2559 0.4988 0.4874 0.071 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
C1 O1 1.441(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N2 1.132(3) . ?
C2 C3 1.436(4) . ?
C3 N1 1.276(3) . ?
C3 C4 1.484(3) . ?
C4 O2 1.216(3) . ?
C4 N3 1.359(3) . ?
C5 O3 1.230(3) . ?
C5 N4 1.315(3) . ?
C5 N3 1.409(3) . ?
C6 N4 1.458(3) . ?
C6 C7 1.493(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.207(3) . ?
C8 O5 1.320(3) . ?
C8 C9 1.494(3) . ?
C9 C9 1.502(5) 3_656 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 O1 1.364(2) . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
O5 H5O 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 C3 177.7(3) . . ?
N1 C3 C2 122.9(2) . . ?
N1 C3 C4 119.9(2) . . ?
C2 C3 C4 117.2(2) . . ?
O2 C4 N3 125.5(2) . . ?
O2 C4 C3 119.0(2) . . ?
N3 C4 C3 115.5(2) . . ?
O3 C5 N4 124.2(2) . . ?
O3 C5 N3 118.4(2) . . ?
N4 C5 N3 117.4(2) . . ?
N4 C6 C7 112.7(2) . . ?
N4 C6 H6A 109.0 . . ?
C7 C6 H6A 109.0 . . ?
N4 C6 H6B 109.0 . . ?
C7 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 O5 122.6(2) . . ?
O4 C8 C9 124.8(2) . . ?
O5 C8 C9 112.6(2) . . ?
C8 C9 C9 113.7(2) . 3_656 ?
C8 C9 H9A 108.8 . . ?
C9 C9 H9A 108.8 3_656 . ?
C8 C9 H9B 108.8 . . ?
C9 C9 H9B 108.8 3_656 . ?
H9A C9 H9B 107.7 . . ?
C3 N1 O1 112.66(19) . . ?
C4 N3 C5 127.0(2) . . ?
C4 N3 H3 116.5 . . ?
C5 N3 H3 116.5 . . ?
C5 N4 C6 122.2(2) . . ?
C5 N4 H4 118.9 . . ?
C6 N4 H4 118.9 . . ?
N1 O1 C1 110.07(19) . . ?
C8 O5 H5O 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
N1 C3 C4 O2 168.6(2) . . . . ?
C2 C3 C4 O2 -8.5(3) . . . . ?
N1 C3 C4 N3 -9.8(3) . . . . ?
C2 C3 C4 N3 173.1(2) . . . . ?
O4 C8 C9 C9 0.8(4) . . . 3_656 ?
O5 C8 C9 C9 -179.7(2) . . . 3_656 ?
C2 C3 N1 O1 -0.4(3) . . . . ?
C4 C3 N1 O1 -177.32(19) . . . . ?
O2 C4 N3 C5 -7.0(4) . . . . ?
C3 C4 N3 C5 171.34(19) . . . . ?
O3 C5 N3 C4 -174.9(2) . . . . ?
N4 C5 N3 C4 4.1(3) . . . . ?
O3 C5 N4 C6 -2.0(3) . . . . ?
N3 C5 N4 C6 179.07(19) . . . . ?
C7 C6 N4 C5 -85.4(3) . . . . ?
C3 N1 O1 C1 179.1(2) . . . . ?

_refine_diff_density_max         0.147
_refine_diff_density_min         -0.195
_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_1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2365738'
loop_
_audit_author_name
_audit_author_address
'jiang zhouyu'
;Southeast university
China
;
_audit_update_record             
;
2024-06-26 deposited with the CCDC.	2024-07-15 downloaded from the CCDC.
;
_audit_creation_date             2024-06-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H10 N4 O3, C7 H6 O3'
_chemical_formula_sum            'C14 H16 N4 O6'
_chemical_formula_weight         336.31
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   4.9580(2)
_cell_length_b                   11.3093(6)
_cell_length_c                   14.6326(8)
_cell_angle_alpha                86.267(2)
_cell_angle_beta                 81.573(2)
_cell_angle_gamma                83.375(2)
_cell_volume                     805.22(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2089
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      62.35
_cell_measurement_theta_min      3.06
_shelx_estimated_absorpt_T_max   0.849
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.940
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1188 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.7794.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   0.864
_exptl_transmission_factor_min   0.864
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2803
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.580
_diffrn_reflns_theta_max         66.580
_diffrn_reflns_theta_min         3.057
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2140
_reflns_number_total             2803
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0703
_refine_ls_restrained_S_all      1.112
_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)+(0.0993P)²+0.5907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2215
_refine_ls_wR_factor_ref         0.2291
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(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:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), N3(H3), N4(H4)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C7(H7A,H7B,H7C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4A), O6(H6)
;
_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
C1 C 0.6003(10) 0.9464(4) 0.6197(3) 0.0941(14) Uani 1 1 d . . . . .
H1A H 0.6175 1.0275 0.5980 0.141 Uiso 1 1 calc R U . . .
H1B H 0.6034 0.9391 0.6853 0.141 Uiso 1 1 calc R U . . .
H1C H 0.4302 0.9236 0.6063 0.141 Uiso 1 1 calc R U . . .
C2 C 1.2297(8) 0.7206(3) 0.5045(3) 0.0698(9) Uani 1 1 d . . . . .
C3 C 1.0148(7) 0.6837(3) 0.5745(2) 0.0619(8) Uani 1 1 d . . . . .
C4 C 1.0402(7) 0.5560(3) 0.6075(2) 0.0640(9) Uani 1 1 d . . . . .
C5 C 0.8280(7) 0.4067(3) 0.7161(3) 0.0612(8) Uani 1 1 d . . . . .
C6 C 1.0293(8) 0.2015(3) 0.7304(3) 0.0800(11) Uani 1 1 d . . . . .
H6A H 1.1372 0.1484 0.6862 0.096 Uiso 1 1 calc R U . . .
H6B H 0.8426 0.1805 0.7395 0.096 Uiso 1 1 calc R U . . .
C7 C 1.1403(10) 0.1826(4) 0.8196(4) 0.0985(15) Uani 1 1 d . . . . .
H7A H 1.3258 0.2024 0.8112 0.148 Uiso 1 1 calc R U . . .
H7B H 1.1366 0.1007 0.8410 0.148 Uiso 1 1 calc R U . . .
H7C H 1.0303 0.2327 0.8646 0.148 Uiso 1 1 calc R U . . .
C8 C 1.1719(7) 0.6251(3) 0.8241(2) 0.0624(8) Uani 1 1 d . . . . .
C9 C 0.9325(7) 0.6966(3) 0.8709(2) 0.0626(8) Uani 1 1 d . . . . .
C10 C 0.7530(8) 0.6468(4) 0.9412(3) 0.0743(10) Uani 1 1 d . . . . .
H10 H 0.7850 0.5665 0.9588 0.089 Uiso 1 1 calc R U . . .
C11 C 0.5284(8) 0.7149(4) 0.9850(3) 0.0853(12) Uani 1 1 d . . . . .
H11 H 0.4090 0.6810 1.0318 0.102 Uiso 1 1 calc R U . . .
C12 C 0.4830(9) 0.8341(4) 0.9587(3) 0.0899(13) Uani 1 1 d . . . . .
H12 H 0.3308 0.8801 0.9877 0.108 Uiso 1 1 calc R U . . .
C13 C 0.6578(9) 0.8861(4) 0.8905(3) 0.0842(12) Uani 1 1 d . . . . .
H13 H 0.6250 0.9667 0.8742 0.101 Uiso 1 1 calc R U . . .
C14 C 0.8849(8) 0.8179(3) 0.8456(3) 0.0694(9) Uani 1 1 d . . . . .
N1 N 0.8132(6) 0.7557(2) 0.6103(2) 0.0678(8) Uani 1 1 d . . . . .
N2 N 1.3980(8) 0.7517(3) 0.4503(3) 0.0881(10) Uani 1 1 d . . . . .
N3 N 0.8414(5) 0.5222(2) 0.67404(19) 0.0606(7) Uani 1 1 d . . . . .
H3 H 0.7112 0.5760 0.6925 0.073 Uiso 1 1 calc R U . . .
N4 N 1.0304(6) 0.3239(2) 0.6918(2) 0.0693(8) Uani 1 1 d . . . . .
H4 H 1.1669 0.3423 0.6522 0.083 Uiso 1 1 calc R U . . .
O1 O 0.8248(6) 0.8698(2) 0.57405(19) 0.0799(8) Uani 1 1 d . . . . .
O2 O 1.2363(6) 0.4918(2) 0.5730(2) 0.0927(10) Uani 1 1 d . . . . .
O3 O 0.6261(5) 0.3890(2) 0.7730(2) 0.0793(8) Uani 1 1 d . . . . .
O4 O 1.2039(5) 0.5129(2) 0.85395(19) 0.0763(8) Uani 1 1 d . . . . .
H4A H 1.3404 0.4788 0.8242 0.114 Uiso 1 1 calc R U . . .
O5 O 1.3306(5) 0.6656(2) 0.75958(18) 0.0736(7) Uani 1 1 d . . . . .
O6 O 1.0519(6) 0.8729(2) 0.7788(2) 0.0870(8) Uani 1 1 d . . . . .
H6 H 1.1843 0.8259 0.7603 0.131 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 O1 1.439(5) . ?
C2 C3 1.444(5) . ?
C2 N2 1.134(5) . ?
C3 C4 1.491(5) . ?
C3 N1 1.285(4) . ?
C4 N3 1.350(4) . ?
C4 O2 1.211(4) . ?
C5 N3 1.411(4) . ?
C5 N4 1.317(4) . ?
C5 O3 1.231(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.484(6) . ?
C6 N4 1.461(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.465(5) . ?
C8 O4 1.314(4) . ?
C8 O5 1.236(4) . ?
C9 C10 1.392(5) . ?
C9 C14 1.400(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.394(5) . ?
C14 O6 1.353(5) . ?
N1 O1 1.366(3) . ?
N3 H3 0.8600 . ?
N4 H4 0.8600 . ?
O4 H4A 0.8200 . ?
O6 H6 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
N2 C2 C3 178.6(4) . . ?
C2 C3 C4 116.7(3) . . ?
N1 C3 C2 123.3(3) . . ?
N1 C3 C4 119.9(3) . . ?
N3 C4 C3 116.6(3) . . ?
O2 C4 C3 117.6(3) . . ?
O2 C4 N3 125.7(3) . . ?
N4 C5 N3 118.3(3) . . ?
O3 C5 N3 118.0(3) . . ?
O3 C5 N4 123.7(3) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
N4 C6 H6A 108.9 . . ?
N4 C6 H6B 108.9 . . ?
N4 C6 C7 113.4(3) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 C9 115.2(3) . . ?
O5 C8 C9 122.9(3) . . ?
O5 C8 O4 121.8(3) . . ?
C10 C9 C8 121.3(3) . . ?
C10 C9 C14 119.2(3) . . ?
C14 C9 C8 119.5(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.2(4) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 C9 119.4(4) . . ?
O6 C14 C9 122.6(3) . . ?
O6 C14 C13 118.0(4) . . ?
C3 N1 O1 112.4(3) . . ?
C4 N3 C5 125.9(3) . . ?
C4 N3 H3 117.0 . . ?
C5 N3 H3 117.0 . . ?
C5 N4 C6 121.8(3) . . ?
C5 N4 H4 119.1 . . ?
C6 N4 H4 119.1 . . ?
N1 O1 C1 109.5(3) . . ?
C8 O4 H4A 109.5 . . ?
C14 O6 H6 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
C2 C3 C4 N3 178.9(3) . . . . ?
C2 C3 C4 O2 -0.7(5) . . . . ?
C2 C3 N1 O1 0.6(5) . . . . ?
C3 C4 N3 C5 -178.8(3) . . . . ?
C3 N1 O1 C1 -177.6(3) . . . . ?
C4 C3 N1 O1 178.4(3) . . . . ?
C7 C6 N4 C5 -85.7(5) . . . . ?
C8 C9 C10 C11 179.9(4) . . . . ?
C8 C9 C14 C13 -179.7(3) . . . . ?
C8 C9 C14 O6 0.1(5) . . . . ?
C9 C10 C11 C12 -0.2(6) . . . . ?
C10 C9 C14 C13 -0.5(5) . . . . ?
C10 C9 C14 O6 179.2(3) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
C12 C13 C14 C9 -0.2(6) . . . . ?
C12 C13 C14 O6 -179.9(4) . . . . ?
C14 C9 C10 C11 0.8(6) . . . . ?
N1 C3 C4 N3 1.0(5) . . . . ?
N1 C3 C4 O2 -178.6(4) . . . . ?
N3 C5 N4 C6 -178.6(3) . . . . ?
N4 C5 N3 C4 2.7(5) . . . . ?
O2 C4 N3 C5 0.7(6) . . . . ?
O3 C5 N3 C4 -176.8(3) . . . . ?
O3 C5 N4 C6 0.9(6) . . . . ?
O4 C8 C9 C10 -0.7(5) . . . . ?
O4 C8 C9 C14 178.4(3) . . . . ?
O5 C8 C9 C10 177.7(3) . . . . ?
O5 C8 C9 C14 -3.1(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
