# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2270635'
loop_
_audit_author_name
_audit_author_address
'Ennio Zangrando'
;University of Trieste
Italy
;
_audit_update_record             
;
2023-06-18 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H16 N O3, 0.5(C6 H8 O4)'
_chemical_formula_sum            'C9 H20 N O5'
_chemical_formula_weight         222.26

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                   5.4015(8)
_cell_length_b                   14.376(2)
_cell_length_c                   14.421(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.264(7)
_cell_angle_gamma                90
_cell_volume                     1116.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5498
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20379
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.833
_diffrn_reflns_theta_max         28.414
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2773
_reflns_number_gt                2405
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0772P)²+0.3318P] 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     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.032(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2773
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1437
_refine_ls_wR_factor_gt          0.1374
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
O1 O 0.4823(2) 0.73263(10) 0.51395(9) 0.0557(3) Uani 1 1 d . . . . .
H1 H 0.480(5) 0.7824(18) 0.5503(18) 0.084 Uiso 1 1 d . U . . .
O2 O 0.43803(19) 0.48741(8) 0.63237(8) 0.0444(3) Uani 1 1 d . . . . .
H2 H 0.373(4) 0.4573(17) 0.6672(16) 0.067 Uiso 1 1 d . U . . .
O3 O 0.5002(2) 0.70418(8) 0.77288(9) 0.0503(3) Uani 1 1 d . . . . .
H3 H 0.453(5) 0.7538(18) 0.7689(18) 0.075 Uiso 1 1 d . U . . .
N1 N 0.78898(18) 0.63039(7) 0.63976(7) 0.0299(2) Uani 1 1 d . . . . .
H1N H 0.633(3) 0.6387(11) 0.6394(11) 0.036 Uiso 1 1 d . U . . .
C1 C 0.8933(3) 0.70857(11) 0.58620(11) 0.0463(4) Uani 1 1 d . . . . .
H1A H 1.061049 0.693216 0.571753 0.056 Uiso 1 1 calc R U . . .
H1B H 0.900574 0.764482 0.623971 0.056 Uiso 1 1 calc R U . . .
C2 C 0.7356(3) 0.72642(12) 0.49720(11) 0.0501(4) Uani 1 1 d . . . . .
H2A H 0.787823 0.783957 0.469445 0.060 Uiso 1 1 calc R U . . .
H2B H 0.758908 0.676347 0.453611 0.060 Uiso 1 1 calc R U . . .
C3 C 0.8313(3) 0.53879(10) 0.59385(11) 0.0417(3) Uani 1 1 d . . . . .
H3A H 0.783268 0.544167 0.527910 0.050 Uiso 1 1 calc R U . . .
H3B H 1.007055 0.524264 0.600676 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6897(3) 0.46070(10) 0.63312(11) 0.0432(3) Uani 1 1 d . . . . .
H4A H 0.705297 0.405040 0.595974 0.052 Uiso 1 1 calc R U . . .
H4B H 0.754968 0.447444 0.696224 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8802(3) 0.63204(11) 0.74028(10) 0.0446(3) Uani 1 1 d . . . . .
H5A H 1.059102 0.639680 0.745768 0.054 Uiso 1 1 calc R U . . .
H5B H 0.841030 0.573429 0.769128 0.054 Uiso 1 1 calc R U . . .
C6 C 0.7605(3) 0.71094(11) 0.78974(11) 0.0487(4) Uani 1 1 d . . . . .
H6A H 0.805790 0.707419 0.856016 0.058 Uiso 1 1 calc R U . . .
H6B H 0.817841 0.770099 0.767081 0.058 Uiso 1 1 calc R U . . .
O4 O 0.0140(2) 0.37743(10) 0.87168(9) 0.0593(4) Uani 1 1 d . . . . .
O5 O 0.2174(2) 0.37708(8) 0.74578(8) 0.0523(3) Uani 1 1 d . . . . .
C7 C 0.1927(2) 0.40191(10) 0.82811(10) 0.0393(3) Uani 1 1 d . . . . .
C8 C 0.3931(3) 0.46380(10) 0.87422(10) 0.0421(3) Uani 1 1 d . . . . .
H8A H 0.553539 0.439265 0.860440 0.051 Uiso 1 1 calc R U . . .
H8B H 0.377184 0.525269 0.846683 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3889(3) 0.47339(11) 0.97836(10) 0.0442(3) Uani 1 1 d . . . . .
H9A H 0.386110 0.411899 1.005948 0.053 Uiso 1 1 calc R U . . .
H9B H 0.237995 0.505302 0.992458 0.053 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 C2 1.409(2) . ?
O1 H1 0.89(3) . ?
O2 C4 1.4120(17) . ?
O2 H2 0.77(2) . ?
O3 C6 1.412(2) . ?
O3 H3 0.76(3) . ?
N1 C5 1.4961(17) . ?
N1 C1 1.4974(18) . ?
N1 C3 1.4989(16) . ?
N1 H1N 0.853(17) . ?
C1 C2 1.509(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.493(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.510(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O4 C7 1.2407(18) . ?
O5 C7 1.2565(19) . ?
C7 C8 1.5161(19) . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.518(3) 3_667 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 101.9(17) . . ?
C4 O2 H2 109.2(17) . . ?
C6 O3 H3 105.9(19) . . ?
C5 N1 C1 112.23(11) . . ?
C5 N1 C3 113.07(11) . . ?
C1 N1 C3 110.86(11) . . ?
C5 N1 H1N 104.9(10) . . ?
C1 N1 H1N 107.6(11) . . ?
C3 N1 H1N 107.7(11) . . ?
N1 C1 C2 110.84(12) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
O1 C2 C1 111.04(13) . . ?
O1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 N1 113.19(11) . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N1 C3 H3B 108.9 . . ?
H3A C3 H3B 107.8 . . ?
O2 C4 C3 108.21(12) . . ?
O2 C4 H4A 110.1 . . ?
C3 C4 H4A 110.1 . . ?
O2 C4 H4B 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
N1 C5 C6 110.36(11) . . ?
N1 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
O3 C6 C5 108.81(12) . . ?
O3 C6 H6A 109.9 . . ?
C5 C6 H6A 109.9 . . ?
O3 C6 H6B 109.9 . . ?
C5 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
O4 C7 O5 122.63(14) . . ?
O4 C7 C8 120.07(14) . . ?
O5 C7 C8 117.29(12) . . ?
C9 C8 C7 115.27(12) . . ?
C9 C8 H8A 108.5 . . ?
C7 C8 H8A 108.5 . . ?
C9 C8 H8B 108.5 . . ?
C7 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C9 112.66(15) . 3_667 ?
C8 C9 H9A 109.1 . . ?
C9 C9 H9A 109.1 3_667 . ?
C8 C9 H9B 109.1 . . ?
C9 C9 H9B 109.1 3_667 . ?
H9A C9 H9B 107.8 . . ?

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
O1 H1 O4 0.89(3) 1.77(3) 2.6551(19) 176(3) 2_556 yes
O2 H2 O5 0.77(2) 1.86(2) 2.6268(16) 176(2) . yes
O3 H3 O5 0.76(3) 2.00(3) 2.7539(16) 172(3) 2_556 yes
N1 H1N O1 0.853(17) 2.353(16) 2.7835(16) 111.7(13) . yes
N1 H1N O3 0.853(17) 2.303(16) 2.7729(15) 114.9(12) . yes
C1 H1A O1 0.97 2.54 3.438(2) 153.1 1_655 yes
C3 H3A O2 0.97 2.56 3.4921(19) 160.6 3_666 yes
C3 H3B O2 0.97 2.40 3.3652(18) 174.8 1_655 yes
C5 H5A O3 0.97 2.56 3.504(2) 164.6 1_655 yes
C6 H6A O1 0.97 2.55 3.4599(19) 155.7 4_676 yes
C8 H8A O4 0.97 2.64 3.579(2) 164.6 1_655 yes

_refine_diff_density_max         0.412
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_dmso
_database_code_depnum_ccdc_archive 'CCDC 2308950'
loop_
_audit_author_name
_audit_author_address
'Deepak Chopra'
;IISER Bhopal
India
;
_audit_update_record             
;
2023-11-19 deposited with the CCDC.	2024-04-18 downloaded from the CCDC.
;
_audit_creation_date             2023-11-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H8 O4, 2(C6 H16 N O3)'
_chemical_formula_sum            'C18 H40 N2 O10'
_chemical_formula_weight         444.52
_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      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                   5.3882(2)
_cell_length_b                   14.1701(4)
_cell_length_c                   14.4214(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.4020(10)
_cell_angle_gamma                90
_cell_volume                     1096.20(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      79.81
_cell_measurement_theta_min      4.38
_shelx_estimated_absorpt_T_max   0.955
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.918
_exptl_absorpt_correction_T_max  0.5179
_exptl_absorpt_correction_T_min  0.3161
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1147 before and 0.0696 after correction.
The Ratio of minimum to maximum transmission is 0.6103.
The λ/2 correction factor is Not present.
;
_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    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.066
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            30140
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.941
_diffrn_reflns_theta_min         4.384
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2079
_reflns_number_total             2322
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         2322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.020
_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)+(0.0330P)²+0.4106P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0787
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C9(H9A,H9B), C8(H8A,H8B),
 C6(H6A,H6B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.44185(14) 0.51537(6) 0.62950(5) 0.02057(18) Uani 1 1 d . . . . .
O5 O 0.50434(15) 0.29968(6) 0.77424(6) 0.02217(19) Uani 1 1 d . . . . .
O2 O 0.22126(14) 0.62711(5) 0.74189(5) 0.02201(19) Uani 1 1 d . . . . .
O1 O 0.00526(14) 0.61894(6) 0.86529(6) 0.02287(19) Uani 1 1 d . . . . .
O4 O 0.48146(15) 0.26382(6) 0.51747(6) 0.02337(19) Uani 1 1 d . . . . .
N1 N 0.79437(16) 0.37093(6) 0.64090(6) 0.01522(19) Uani 1 1 d . . . . .
C5 C 0.6954(2) 0.54329(8) 0.63136(8) 0.0193(2) Uani 1 1 d . . . . .
H5A H 0.763230 0.557728 0.695986 0.023 Uiso 1 1 calc R U . . .
H5B H 0.709956 0.600520 0.592868 0.023 Uiso 1 1 calc R U . . .
C4 C 0.8378(2) 0.46275(7) 0.59313(7) 0.0184(2) Uani 1 1 d . . . . .
H4A H 0.786882 0.456092 0.525683 0.022 Uiso 1 1 calc R U . . .
H4B H 1.018176 0.477565 0.600658 0.022 Uiso 1 1 calc R U . . .
C1 C 0.19241(19) 0.59859(7) 0.82393(7) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.39668(19) 0.53703(8) 0.87238(7) 0.0189(2) Uani 1 1 d . . . . .
H2A H 0.560324 0.564476 0.861402 0.023 Uiso 1 1 calc R U . . .
H2B H 0.386898 0.473678 0.843313 0.023 Uiso 1 1 calc R U . . .
C3 C 0.38567(19) 0.52568(8) 0.97701(7) 0.0201(2) Uani 1 1 d . . . . .
H3A H 0.233789 0.489850 0.988452 0.024 Uiso 1 1 calc R U . . .
H3B H 0.374016 0.588780 1.005742 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7673(2) 0.29121(8) 0.79256(8) 0.0214(2) Uani 1 1 d . . . . .
H9A H 0.823251 0.229436 0.770120 0.026 Uiso 1 1 calc R U . . .
H9B H 0.815491 0.295317 0.860401 0.026 Uiso 1 1 calc R U . . .
C8 C 0.8881(2) 0.37061(8) 0.74247(7) 0.0195(2) Uani 1 1 d . . . . .
H8A H 0.849191 0.431814 0.770874 0.023 Uiso 1 1 calc R U . . .
H8B H 1.071423 0.362402 0.749135 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8989(2) 0.29028(8) 0.58889(8) 0.0202(2) Uani 1 1 d . . . . .
H6A H 0.908731 0.233163 0.628606 0.024 Uiso 1 1 calc R U . . .
H6B H 1.069601 0.306134 0.573999 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7352(2) 0.27032(8) 0.49935(8) 0.0215(2) Uani 1 1 d . . . . .
H7A H 0.755019 0.321546 0.453954 0.026 Uiso 1 1 calc R U . . .
H7B H 0.787747 0.210389 0.471822 0.026 Uiso 1 1 calc R U . . .
H1 H 0.624(3) 0.3635(10) 0.6387(9) 0.024(3) Uiso 1 1 d . . . . .
H5 H 0.440(3) 0.2411(13) 0.7700(12) 0.045(5) Uiso 1 1 d . . . . .
H4 H 0.471(3) 0.2129(13) 0.5522(12) 0.046(5) Uiso 1 1 d . . . . .
H3 H 0.372(3) 0.5499(13) 0.6673(12) 0.045(5) 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
O3 C5 1.4199(13) . ?
O3 H3 0.846(18) . ?
O5 C9 1.4218(14) . ?
O5 H5 0.900(19) . ?
O2 C1 1.2736(13) . ?
O1 C1 1.2525(13) . ?
O4 C7 1.4188(13) . ?
O4 H4 0.883(18) . ?
N1 C4 1.5009(13) . ?
N1 C8 1.5039(13) . ?
N1 C6 1.5051(13) . ?
N1 H1 0.920(14) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.5086(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C1 C2 1.5217(15) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5242(15) . ?
C3 C3 1.528(2) 3_667 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.5167(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5201(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 H3 108.2(12) . . ?
C9 O5 H5 107.8(11) . . ?
C7 O4 H4 105.8(11) . . ?
C4 N1 C8 113.39(8) . . ?
C4 N1 C6 110.34(8) . . ?
C4 N1 H1 106.4(9) . . ?
C8 N1 C6 112.09(8) . . ?
C8 N1 H1 106.0(8) . . ?
C6 N1 H1 108.3(9) . . ?
O3 C5 H5A 110.2 . . ?
O3 C5 H5B 110.2 . . ?
O3 C5 C4 107.71(9) . . ?
H5A C5 H5B 108.5 . . ?
C4 C5 H5A 110.2 . . ?
C4 C5 H5B 110.2 . . ?
N1 C4 C5 112.41(8) . . ?
N1 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
O2 C1 C2 117.52(9) . . ?
O1 C1 O2 122.92(10) . . ?
O1 C1 C2 119.56(9) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C1 C2 C3 114.91(9) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 C3 112.03(11) . 3_667 ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C3 C3 H3A 109.2 3_667 . ?
C3 C3 H3B 109.2 3_667 . ?
H3A C3 H3B 107.9 . . ?
O5 C9 H9A 110.0 . . ?
O5 C9 H9B 110.0 . . ?
O5 C9 C8 108.29(9) . . ?
H9A C9 H9B 108.4 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
N1 C8 C9 110.25(9) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 C7 110.50(9) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
O4 C7 C6 110.34(8) . . ?
O4 C7 H7A 109.6 . . ?
O4 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?

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
O3 C5 C4 N1 -52.16(11) . . . . ?
O5 C9 C8 N1 -53.69(11) . . . . ?
O2 C1 C2 C3 165.33(9) . . . . ?
O1 C1 C2 C3 -14.76(14) . . . . ?
N1 C6 C7 O4 -48.97(12) . . . . ?
C4 N1 C8 C9 161.56(8) . . . . ?
C4 N1 C6 C7 -73.65(11) . . . . ?
C1 C2 C3 C3 -172.39(11) . . . 3_667 ?
C8 N1 C4 C5 -64.21(11) . . . . ?
C8 N1 C6 C7 158.95(9) . . . . ?
C6 N1 C4 C5 169.12(9) . . . . ?
C6 N1 C8 C9 -72.69(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
