# 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. 
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data_MAT_HES
_database_code_depnum_ccdc_archive 'CCDC 2322345'
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2023-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 O6, C15 H25 N2 O'
_chemical_formula_sum            'C31 H38 N2 O7'
_chemical_formula_weight         550.63
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.39690(10)
_cell_length_b                   10.20610(10)
_cell_length_c                   31.5288(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2702.01(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10073
_cell_measurement_temperature    212.99(10)
_cell_measurement_theta_max      76.2750
_cell_measurement_theta_min      4.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.782
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62347
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            14592
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.422
_diffrn_reflns_theta_min         4.554
_diffrn_ambient_temperature      213.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     63.00 122.00   1.00    0.10    --   48.42-164.00 162.00   59
  2  ω     34.00 105.00   1.00    0.20    --  106.65 -99.00 120.00   71
  3  ω    -95.00 -58.00   1.00    0.20    --  -91.75 164.00-172.00   37
  4  ω   -138.00 -79.00   1.00    0.20    --  -91.75-116.00 -48.00   59
  5  ω   -143.00-117.00   1.00    0.20    --  -91.75 -82.00-160.00   26
  6  ω   -120.00 -73.00   1.00    0.10    --  -48.42-125.00 -30.00   47
  7  ω    -24.00  39.00   1.00    0.10    --   48.42 -38.00 -60.00   63
  8  ω     36.00  65.00   1.00    0.20    --  106.65 -57.00-180.00   29
  9  ω     52.00  87.00   1.00    0.20    --  106.65 -77.00 -90.00   35
 10  ω     34.00  66.00   1.00    0.20    --  106.65 -57.00 -90.00   32
 11  ω     99.00 178.00   1.00    0.20    --  106.65  41.00 176.00   79
 12  ω   -108.00 -79.00   1.00    0.20    --  -91.75 -41.00  23.00   29
 13  ω    -66.00 -22.00   1.00    0.20    --  -91.75  57.00  30.00   44
 14  ω    143.00 169.00   1.00    0.20    --  106.65  57.00-150.00   26
 15  ω     92.00 136.00   1.00    0.20    --  106.65  57.00-150.00   44
 16  ω     95.00 170.00   1.00    0.20    --  106.65 125.00   0.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.898
_reflns_number_gt                5019
_reflns_number_total             5298
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.796
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5298
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.106
_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)+(0.0732P)²+0.2622P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1201
_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, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H3-O3
 0.82 with sigma of 0.02
 H5A-O5
 0.82 with sigma of 0.02
 H2-N2
 0.87 with sigma of 0.02
3. Others
 Sof(C22B)=Sof(H22B)=Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C20B)=Sof(O4B)=1-FVAR(1)
 Sof(O4A)=Sof(C20A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=FVAR(1)
4.a Riding coordinates:
 O5(H5A), O3(H3), N2(H2)
4.b Ternary CH refined with riding coordinates:
 C15(H15), C6(H6), C5(H5), C13(H13), C22A(H22A), C22B(H22B)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B), C8(H8A,H8B), C14(H14A,H14B), C12(H12A,H12B),
 C9(H9A,H9B), C7(H7A,H7B), C4(H4A,H4B), C2(H2A,H2B), C3(H3A,H3B), C21A(H21A,
 H21B), C21B(H21C,H21D)
4.d Aromatic/amide H refined with riding coordinates:
 C30(H30), C17(H17), C24(H24), C27(H27), C28(H28)
4.e Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.4818(2) 0.94641(18) 0.62158(6) 0.0358(4) Uani 1 1 d . . . . .
O5 O 0.6338(2) -0.00107(19) 0.55221(6) 0.0454(5) Uani 1 1 d D . . . .
H5A H 0.582245 -0.012404 0.574682 0.054 Uiso 1 1 d DR U . . .
O6 O 0.8273(2) 0.0528(2) 0.49008(6) 0.0432(4) Uani 1 1 d . . . . .
O7 O 0.6992(3) 0.52577(17) 0.60661(6) 0.0434(5) Uani 1 1 d . . . . .
O3 O 0.6425(3) 0.7199(2) 0.74478(6) 0.0485(5) Uani 1 1 d D . . . .
H3 H 0.674546 0.636054 0.747863 0.058 Uiso 1 1 d DR U . . .
N2 N 0.1793(2) 0.97568(19) 0.59540(6) 0.0317(4) Uani 1 1 d D . . . .
H2 H 0.281223 0.932209 0.605538 0.038 Uiso 1 1 d DR U . . .
N1 N 0.1567(3) 0.6471(2) 0.64267(7) 0.0372(5) Uani 1 1 d . . . . .
O4A O 0.7172(12) 0.4762(8) 0.7371(3) 0.0549(18) Uani 0.641(17) 1 d . . P A 1
O1 O 0.2267(4) 0.4350(2) 0.63499(8) 0.0738(8) Uani 1 1 d . . . . .
C26 C 0.8197(3) 0.1433(2) 0.52171(8) 0.0328(5) Uani 1 1 d . . . . .
C15 C 0.0394(3) 0.8841(3) 0.60175(8) 0.0338(5) Uani 1 1 d . . . . .
H15 H -0.056580 0.928781 0.590645 0.041 Uiso 1 1 calc R U . . .
C19 C 0.6715(3) 0.6146(2) 0.67726(8) 0.0340(5) Uani 1 1 d . . . . .
C29 C 0.6574(3) 0.6264(2) 0.63280(8) 0.0320(5) Uani 1 1 d . . . . .
C25 C 0.7159(3) 0.1122(2) 0.55524(7) 0.0343(5) Uani 1 1 d . . . . .
C16 C 0.5489(3) 0.8446(2) 0.63923(8) 0.0304(5) Uani 1 1 d . . . . .
C30 C 0.6011(3) 0.7383(2) 0.61396(7) 0.0317(5) Uani 1 1 d . . . . .
H30 H 0.597244 0.744420 0.584230 0.038 Uiso 1 1 calc R U . . .
C17 C 0.5676(3) 0.8370(2) 0.68374(8) 0.0346(5) Uani 1 1 d . . . . .
H17 H 0.539103 0.908780 0.700810 0.042 Uiso 1 1 calc R U . . .
C18 C 0.6271(3) 0.7257(3) 0.70208(7) 0.0347(5) Uani 1 1 d . . . . .
C10 C 0.2096(3) 1.0012(3) 0.54924(8) 0.0397(6) Uani 1 1 d . . . . .
H10A H 0.303202 1.057836 0.546300 0.048 Uiso 1 1 calc R U . . .
H10B H 0.118076 1.047371 0.537069 0.048 Uiso 1 1 calc R U . . .
C6 C 0.0112(3) 0.8569(3) 0.64890(8) 0.0377(5) Uani 1 1 d . . . . .
H6 H -0.091163 0.809129 0.650956 0.045 Uiso 1 1 calc R U . . .
C24 C 0.7021(4) 0.1988(3) 0.58908(8) 0.0409(6) Uani 1 1 d . . . . .
H24 H 0.632921 0.178597 0.611585 0.049 Uiso 1 1 calc R U . . .
C11 C 0.2371(4) 0.8759(3) 0.52505(8) 0.0435(6) Uani 1 1 d . . . . .
H11A H 0.334524 0.833784 0.535382 0.052 Uiso 1 1 calc R U . . .
H11B H 0.251804 0.896080 0.494915 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1389(3) 0.7676(3) 0.66856(7) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.241570 0.815204 0.668047 0.042 Uiso 1 1 calc R U . . .
C27 C 0.9055(3) 0.2593(3) 0.52320(8) 0.0395(6) Uani 1 1 d . . . . .
H27 H 0.974868 0.280696 0.500840 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1284(4) 1.0793(3) 0.66531(9) 0.0459(7) Uani 1 1 d . . . . .
H8A H 0.107297 1.162742 0.679621 0.055 Uiso 1 1 calc R U . . .
H8B H 0.225463 1.041647 0.677532 0.055 Uiso 1 1 calc R U . . .
C13 C 0.0597(3) 0.7566(3) 0.57686(8) 0.0354(5) Uani 1 1 d . . . . .
H13 H -0.043300 0.709564 0.577993 0.043 Uiso 1 1 calc R U . . .
C14 C 0.1841(3) 0.6685(3) 0.59730(8) 0.0349(5) Uani 1 1 d . . . . .
H14A H 0.184017 0.583594 0.582772 0.042 Uiso 1 1 calc R U . . .
H14B H 0.289506 0.707887 0.593415 0.042 Uiso 1 1 calc R U . . .
C12 C 0.0972(4) 0.7820(3) 0.53018(8) 0.0441(6) Uani 1 1 d . . . . .
H12A H 0.122480 0.698738 0.516220 0.053 Uiso 1 1 calc R U . . .
H12B H 0.003105 0.819074 0.516257 0.053 Uiso 1 1 calc R U . . .
C9 C 0.1532(4) 1.1035(2) 0.61820(9) 0.0409(6) Uani 1 1 d . . . . .
H9A H 0.059669 1.147806 0.606412 0.049 Uiso 1 1 calc R U . . .
H9B H 0.245838 1.160485 0.614060 0.049 Uiso 1 1 calc R U . . .
C23 C 0.7889(5) 0.3147(3) 0.59021(9) 0.0496(7) Uani 1 1 d . . . . .
C1 C 0.1966(4) 0.5271(3) 0.65828(10) 0.0503(7) Uani 1 1 d . . . . .
C7 C -0.0109(4) 0.9861(3) 0.67267(9) 0.0495(7) Uani 1 1 d . . . . .
H7A H -0.109631 1.028036 0.663185 0.059 Uiso 1 1 calc R U . . .
H7B H -0.020793 0.968249 0.703097 0.059 Uiso 1 1 calc R U . . .
C28 C 0.8902(4) 0.3438(3) 0.55726(9) 0.0476(7) Uani 1 1 d . . . . .
H28 H 0.949542 0.421846 0.557879 0.057 Uiso 1 1 calc R U . . .
C4 C 0.1005(4) 0.7343(3) 0.71439(8) 0.0457(6) Uani 1 1 d . . . . .
H4A H 0.107946 0.813651 0.731778 0.055 Uiso 1 1 calc R U . . .
H4B H -0.008811 0.701203 0.716290 0.055 Uiso 1 1 calc R U . . .
C31 C 0.9325(4) 0.0813(3) 0.45567(9) 0.0513(7) Uani 1 1 d . . . . .
H31A H 0.934691 0.007578 0.436252 0.077 Uiso 1 1 calc R U . . .
H31B H 1.038883 0.096811 0.466579 0.077 Uiso 1 1 calc R U . . .
H31C H 0.895452 0.158726 0.440827 0.077 Uiso 1 1 calc R U . . .
C2 C 0.1953(5) 0.5072(4) 0.70596(11) 0.0632(9) Uani 1 1 d . . . . .
H2A H 0.094755 0.465233 0.714027 0.076 Uiso 1 1 calc R U . . .
H2B H 0.281933 0.447325 0.713619 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2138(4) 0.6327(4) 0.73109(9) 0.0582(9) Uani 1 1 d . . . . .
H3A H 0.191512 0.615965 0.761109 0.070 Uiso 1 1 calc R U . . .
H3B H 0.323478 0.664722 0.728675 0.070 Uiso 1 1 calc R U . . .
C20A C 0.7019(12) 0.4919(11) 0.6971(3) 0.0377(17) Uani 0.641(17) 1 d . . P A 1
C21A C 0.7167(14) 0.3751(6) 0.66804(17) 0.0498(18) Uani 0.641(17) 1 d . . P A 1
H21A H 0.611576 0.335894 0.663422 0.060 Uiso 0.641(17) 1 calc R U P A 1
H21B H 0.785710 0.308893 0.681037 0.060 Uiso 0.641(17) 1 calc R U P A 1
C22A C 0.7870(11) 0.4190(5) 0.62579(15) 0.0350(14) Uani 0.641(17) 1 d . . P A 1
H22A H 0.897738 0.448527 0.630758 0.042 Uiso 0.641(17) 1 calc R U P A 1
C22B C 0.708(2) 0.4059(8) 0.6224(3) 0.040(3) Uani 0.359(17) 1 d . . P A 2
H22B H 0.598507 0.373514 0.627937 0.048 Uiso 0.359(17) 1 calc R U P A 2
C21B C 0.8032(19) 0.3968(10) 0.6628(3) 0.041(3) Uani 0.359(17) 1 d . . P A 2
H21C H 0.786340 0.310636 0.675700 0.050 Uiso 0.359(17) 1 calc R U P A 2
H21D H 0.916714 0.405036 0.656020 0.050 Uiso 0.359(17) 1 calc R U P A 2
C20B C 0.7578(16) 0.501(2) 0.6938(6) 0.039(3) Uani 0.359(17) 1 d . . P A 2
O4B O 0.7777(19) 0.4906(17) 0.7310(5) 0.056(3) Uani 0.359(17) 1 d . . P A 2


_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
O2 C16 1.307(3) . ?
O5 H5A 0.8384 . ?
O5 C25 1.349(3) . ?
O6 C26 1.360(3) . ?
O6 C31 1.429(3) . ?
O7 C29 1.364(3) . ?
O7 C22A 1.448(5) . ?
O7 C22B 1.323(9) . ?
O3 H3 0.9018 . ?
O3 C18 1.354(3) . ?
N2 H2 1.0156 . ?
N2 C15 1.514(3) . ?
N2 C10 1.500(3) . ?
N2 C9 1.505(3) . ?
N1 C5 1.483(3) . ?
N1 C14 1.465(3) . ?
N1 C1 1.362(4) . ?
O4A C20A 1.278(12) . ?
O1 C1 1.219(4) . ?
C26 C25 1.406(3) . ?
C26 C27 1.387(4) . ?
C15 H15 0.9900 . ?
C15 C6 1.531(3) . ?
C15 C13 1.529(4) . ?
C19 C29 1.412(3) . ?
C19 C18 1.427(4) . ?
C19 C20A 1.424(11) . ?
C19 C20B 1.463(19) . ?
C29 C30 1.371(3) . ?
C25 C24 1.390(4) . ?
C16 C30 1.415(3) . ?
C16 C17 1.414(4) . ?
C30 H30 0.9400 . ?
C17 H17 0.9400 . ?
C17 C18 1.369(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 C11 1.506(4) . ?
C6 H6 0.9900 . ?
C6 C5 1.537(4) . ?
C6 C7 1.528(4) . ?
C24 H24 0.9400 . ?
C24 C23 1.390(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 C12 1.525(4) . ?
C5 H5 0.9900 . ?
C5 C4 1.519(3) . ?
C27 H27 0.9400 . ?
C27 C28 1.383(4) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.520(4) . ?
C8 C7 1.525(5) . ?
C13 H13 0.9900 . ?
C13 C14 1.522(3) . ?
C13 C12 1.527(4) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C23 C28 1.375(5) . ?
C23 C22A 1.546(6) . ?
C23 C22B 1.537(11) . ?
C1 C2 1.517(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C28 H28 0.9400 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 C3 1.502(5) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C31 H31C 0.9700 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.515(5) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C20A C21A 1.509(12) . ?
C21A H21A 0.9800 . ?
C21A H21B 0.9800 . ?
C21A C22A 1.524(10) . ?
C22A H22A 0.9900 . ?
C22B H22B 0.9900 . ?
C22B C21B 1.506(16) . ?
C21B H21C 0.9800 . ?
C21B H21D 0.9800 . ?
C21B C20B 1.49(2) . ?
C20B O4B 1.19(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
C25 O5 H5A 108.8 . . ?
C26 O6 C31 116.6(2) . . ?
C29 O7 C22A 116.4(3) . . ?
C22B O7 C29 118.8(4) . . ?
C18 O3 H3 100.2 . . ?
C15 N2 H2 110.0 . . ?
C10 N2 H2 103.8 . . ?
C10 N2 C15 111.53(19) . . ?
C10 N2 C9 109.74(19) . . ?
C9 N2 H2 110.5 . . ?
C9 N2 C15 111.02(19) . . ?
C14 N1 C5 115.45(19) . . ?
C1 N1 C5 124.9(2) . . ?
C1 N1 C14 116.6(2) . . ?
O6 C26 C25 115.3(2) . . ?
O6 C26 C27 125.4(2) . . ?
C27 C26 C25 119.3(2) . . ?
N2 C15 H15 107.5 . . ?
N2 C15 C6 111.14(19) . . ?
N2 C15 C13 111.77(19) . . ?
C6 C15 H15 107.5 . . ?
C13 C15 H15 107.5 . . ?
C13 C15 C6 111.2(2) . . ?
C29 C19 C18 117.0(2) . . ?
C29 C19 C20A 121.8(5) . . ?
C29 C19 C20B 117.6(8) . . ?
C18 C19 C20B 124.3(8) . . ?
C20A C19 C18 120.3(5) . . ?
O7 C29 C19 121.0(2) . . ?
O7 C29 C30 117.0(2) . . ?
C30 C29 C19 122.0(2) . . ?
O5 C25 C26 117.2(2) . . ?
O5 C25 C24 123.8(2) . . ?
C24 C25 C26 119.0(2) . . ?
O2 C16 C30 120.2(2) . . ?
O2 C16 C17 120.9(2) . . ?
C17 C16 C30 118.8(2) . . ?
C29 C30 C16 120.1(2) . . ?
C29 C30 H30 120.0 . . ?
C16 C30 H30 120.0 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.3(2) . . ?
C18 C17 H17 119.8 . . ?
O3 C18 C19 119.0(2) . . ?
O3 C18 C17 119.4(2) . . ?
C17 C18 C19 121.5(2) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
N2 C10 C11 111.7(2) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
C15 C6 H6 106.7 . . ?
C15 C6 C5 113.0(2) . . ?
C5 C6 H6 106.7 . . ?
C7 C6 C15 109.8(2) . . ?
C7 C6 H6 106.7 . . ?
C7 C6 C5 113.5(2) . . ?
C25 C24 H24 119.4 . . ?
C23 C24 C25 121.1(2) . . ?
C23 C24 H24 119.4 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C10 C11 C12 111.2(2) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N1 C5 C6 109.9(2) . . ?
N1 C5 H5 108.1 . . ?
N1 C5 C4 111.1(2) . . ?
C6 C5 H5 108.1 . . ?
C4 C5 C6 111.6(2) . . ?
C4 C5 H5 108.1 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C9 C8 C7 110.8(2) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C15 C13 H13 107.3 . . ?
C14 C13 C15 111.23(19) . . ?
C14 C13 H13 107.3 . . ?
C14 C13 C12 111.5(2) . . ?
C12 C13 C15 111.9(2) . . ?
C12 C13 H13 107.3 . . ?
N1 C14 C13 113.2(2) . . ?
N1 C14 H14A 108.9 . . ?
N1 C14 H14B 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.8 . . ?
C11 C12 C13 111.6(2) . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C9 C8 110.2(2) . . ?
N2 C9 H9A 109.6 . . ?
N2 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C24 C23 C22A 126.8(4) . . ?
C24 C23 C22B 107.4(6) . . ?
C28 C23 C24 119.3(3) . . ?
C28 C23 C22A 113.9(4) . . ?
C28 C23 C22B 130.0(5) . . ?
N1 C1 C2 118.5(3) . . ?
O1 C1 N1 121.8(3) . . ?
O1 C1 C2 119.7(3) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 C6 111.8(2) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C27 C28 H28 119.7 . . ?
C23 C28 C27 120.6(3) . . ?
C23 C28 H28 119.7 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C3 C4 C5 110.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
O6 C31 H31A 109.5 . . ?
O6 C31 H31B 109.5 . . ?
O6 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 C1 113.8(3) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C4 C3 C2 109.6(3) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O4A C20A C19 124.2(9) . . ?
O4A C20A C21A 119.6(9) . . ?
C19 C20A C21A 116.2(7) . . ?
C20A C21A H21A 109.8 . . ?
C20A C21A H21B 109.8 . . ?
C20A C21A C22A 109.3(6) . . ?
H21A C21A H21B 108.3 . . ?
C22A C21A H21A 109.8 . . ?
C22A C21A H21B 109.8 . . ?
O7 C22A C23 102.7(4) . . ?
O7 C22A C21A 112.9(6) . . ?
O7 C22A H22A 108.4 . . ?
C23 C22A H22A 108.4 . . ?
C21A C22A C23 115.8(6) . . ?
C21A C22A H22A 108.4 . . ?
O7 C22B C23 109.5(7) . . ?
O7 C22B H22B 108.9 . . ?
O7 C22B C21B 113.8(11) . . ?
C23 C22B H22B 108.9 . . ?
C21B C22B C23 106.5(11) . . ?
C21B C22B H22B 108.9 . . ?
C22B C21B H21C 109.2 . . ?
C22B C21B H21D 109.2 . . ?
H21C C21B H21D 107.9 . . ?
C20B C21B C22B 111.9(10) . . ?
C20B C21B H21C 109.2 . . ?
C20B C21B H21D 109.2 . . ?
C19 C20B C21B 117.2(13) . . ?
O4B C20B C19 119.4(17) . . ?
O4B C20B C21B 123.1(17) . . ?

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
O5 H5A O2 0.84 1.75 2.589(2) 173.8 1_545 yes
O3 H3 O4A 0.90 1.70 2.576(9) 161.7 . yes
O3 H3 O4B 0.90 1.80 2.637(18) 153.4 . yes
N2 H2 O2 1.02 1.76 2.687(3) 149.2 . 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
O2 C16 C30 C29 -173.7(2) . . . . ?
O2 C16 C17 C18 175.1(2) . . . . ?
O5 C25 C24 C23 -179.4(3) . . . . ?
O6 C26 C25 O5 -1.2(3) . . . . ?
O6 C26 C25 C24 179.4(2) . . . . ?
O6 C26 C27 C28 -179.2(2) . . . . ?
O7 C29 C30 C16 177.2(2) . . . . ?
O7 C22B C21B C20B 47.3(19) . . . . ?
N2 C15 C6 C5 -72.2(3) . . . . ?
N2 C15 C6 C7 55.6(3) . . . . ?
N2 C15 C13 C14 73.5(2) . . . . ?
N2 C15 C13 C12 -52.0(3) . . . . ?
N2 C10 C11 C12 56.6(3) . . . . ?
N1 C5 C4 C3 49.2(3) . . . . ?
N1 C1 C2 C3 -23.1(5) . . . . ?
O4A C20A C21A C22A -148.1(8) . . . . ?
O1 C1 C2 C3 159.9(4) . . . . ?
C26 C25 C24 C23 0.0(4) . . . . ?
C26 C27 C28 C23 -0.3(4) . . . . ?
C15 N2 C10 C11 -56.8(3) . . . . ?
C15 N2 C9 C8 58.3(3) . . . . ?
C15 C6 C5 N1 -52.0(3) . . . . ?
C15 C6 C5 C4 -175.7(2) . . . . ?
C15 C6 C7 C8 -54.7(3) . . . . ?
C15 C13 C14 N1 51.4(3) . . . . ?
C15 C13 C12 C11 51.9(3) . . . . ?
C19 C29 C30 C16 -2.6(4) . . . . ?
C19 C20A C21A C22A 31.7(8) . . . . ?
C29 O7 C22A C23 170.7(3) . . . . ?
C29 O7 C22A C21A 45.3(9) . . . . ?
C29 O7 C22B C23 -168.5(6) . . . . ?
C29 O7 C22B C21B -49.3(17) . . . . ?
C29 C19 C18 O3 -178.4(2) . . . . ?
C29 C19 C18 C17 2.5(4) . . . . ?
C29 C19 C20A O4A 179.3(6) . . . . ?
C29 C19 C20A C21A -0.5(8) . . . . ?
C29 C19 C20B C21B -8.7(13) . . . . ?
C29 C19 C20B O4B 176.9(10) . . . . ?
C25 C26 C27 C28 0.2(4) . . . . ?
C25 C24 C23 C28 -0.1(4) . . . . ?
C25 C24 C23 C22A -179.3(4) . . . . ?
C25 C24 C23 C22B 161.4(6) . . . . ?
C16 C17 C18 O3 -179.3(2) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C30 C16 C17 C18 -3.6(3) . . . . ?
C17 C16 C30 C29 4.9(3) . . . . ?
C18 C19 C29 O7 179.1(2) . . . . ?
C18 C19 C29 C30 -1.1(4) . . . . ?
C18 C19 C20A O4A -11.5(9) . . . . ?
C18 C19 C20A C21A 168.6(5) . . . . ?
C18 C19 C20B C21B -176.4(8) . . . . ?
C18 C19 C20B O4B 9.2(16) . . . . ?
C10 N2 C15 C6 179.04(19) . . . . ?
C10 N2 C15 C13 54.2(2) . . . . ?
C10 N2 C9 C8 -177.9(2) . . . . ?
C10 C11 C12 C13 -54.1(3) . . . . ?
C6 C15 C13 C14 -51.3(3) . . . . ?
C6 C15 C13 C12 -176.8(2) . . . . ?
C6 C5 C4 C3 172.2(2) . . . . ?
C24 C23 C28 C27 0.3(5) . . . . ?
C24 C23 C22A O7 -107.2(4) . . . . ?
C24 C23 C22A C21A 16.3(10) . . . . ?
C24 C23 C22B O7 -136.2(9) . . . . ?
C24 C23 C22B C21B 100.3(12) . . . . ?
C5 N1 C14 C13 -53.3(3) . . . . ?
C5 N1 C1 O1 -171.8(3) . . . . ?
C5 N1 C1 C2 11.3(4) . . . . ?
C5 C6 C7 C8 72.8(3) . . . . ?
C5 C4 C3 C2 -62.6(3) . . . . ?
C27 C26 C25 O5 179.4(2) . . . . ?
C27 C26 C25 C24 0.0(3) . . . . ?
C13 C15 C6 C5 53.0(3) . . . . ?
C13 C15 C6 C7 -179.2(2) . . . . ?
C14 N1 C5 C6 52.4(3) . . . . ?
C14 N1 C5 C4 176.3(2) . . . . ?
C14 N1 C1 O1 -12.6(4) . . . . ?
C14 N1 C1 C2 170.5(3) . . . . ?
C14 C13 C12 C11 -73.4(3) . . . . ?
C12 C13 C14 N1 177.1(2) . . . . ?
C9 N2 C15 C6 -58.2(3) . . . . ?
C9 N2 C15 C13 176.93(19) . . . . ?
C9 N2 C10 C11 179.8(2) . . . . ?
C9 C8 C7 C6 55.9(3) . . . . ?
C23 C22B C21B C20B 168.1(9) . . . . ?
C1 N1 C5 C6 -148.2(3) . . . . ?
C1 N1 C5 C4 -24.2(4) . . . . ?
C1 N1 C14 C13 145.5(2) . . . . ?
C1 C2 C3 C4 48.5(4) . . . . ?
C7 C6 C5 N1 -177.9(2) . . . . ?
C7 C6 C5 C4 58.5(3) . . . . ?
C7 C8 C9 N2 -56.9(3) . . . . ?
C28 C23 C22A O7 73.5(6) . . . . ?
C28 C23 C22A C21A -162.9(7) . . . . ?
C28 C23 C22B O7 22.6(15) . . . . ?
C28 C23 C22B C21B -100.9(9) . . . . ?
C31 O6 C26 C25 -179.6(2) . . . . ?
C31 O6 C26 C27 -0.2(4) . . . . ?
C20A C19 C29 O7 -11.4(6) . . . . ?
C20A C19 C29 C30 168.4(5) . . . . ?
C20A C19 C18 O3 12.0(6) . . . . ?
C20A C19 C18 C17 -167.2(5) . . . . ?
C20A C21A C22A O7 -54.0(10) . . . . ?
C20A C21A C22A C23 -172.0(6) . . . . ?
C22A O7 C29 C19 -12.0(5) . . . . ?
C22A O7 C29 C30 168.2(4) . . . . ?
C22A C23 C28 C27 179.6(4) . . . . ?
C22B O7 C29 C19 19.9(9) . . . . ?
C22B O7 C29 C30 -159.9(9) . . . . ?
C22B C23 C28 C27 -156.5(8) . . . . ?
C22B C21B C20B C19 -18.3(16) . . . . ?
C22B C21B C20B O4B 155.8(14) . . . . ?
C20B C19 C29 O7 10.5(8) . . . . ?
C20B C19 C29 C30 -169.7(7) . . . . ?
C20B C19 C18 O3 -10.6(8) . . . . ?
C20B C19 C18 C17 170.2(8) . . . . ?

_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
;
####################################################################### 
# 
# 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_mat-h2o
_database_code_depnum_ccdc_archive 'CCDC 2323096'
loop_
_audit_author_name
_audit_author_address
'Yujing Zhu'
;USTC
China
;
_audit_update_record             
;
2024-01-02 deposited with the CCDC.	2024-01-17 downloaded from the CCDC.
;
_audit_creation_date             2024-01-02
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        matrine-h2o
_chemical_formula_moiety         'C15 H24 N2 O, H2 O'
_chemical_formula_sum            'C15 H27.50 N2 O2.75'
_chemical_formula_weight         279.89
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   11.7266(6)
_cell_length_b                   11.7266(6)
_cell_length_c                   21.9372(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3016.7(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9884
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      56.65
_cell_measurement_theta_min      3.72
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.431
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1402 before and 0.0614 after correction.
The Ratio of minimum to maximum transmission is 0.9073.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1228
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            33397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         56.909
_diffrn_reflns_theta_min         3.718
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_reflns_Friedel_coverage         0.677
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2731
_reflns_number_total             3084
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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  'olex2.refine 1.3 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3084
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0339
_refine_ls_restrained_S_all      1.036
_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)+(0.0419P)²+0.4975P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.9(4)
 0.1(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
3. Restrained distances
 H2c-O2
 0.82 with sigma of 0.02
 H2d-O2
 0.82 with sigma of 0.02
4.a Riding coordinates:
 O2(H2c,H2d)
4.b Ternary CH refined with riding coordinates:
 C13(H13), C15(H15), C6(H6), C5(H5)
4.c Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C3(H3a,H3b), C4(H4a,H4b), C7(H7a,H7b), C2(H2a,H2b), C12(H12a,
 H12b), C8(H8a,H8b), C9(H9a,H9b), C11(H11a,H11b), C10(H10a,H10b)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.13910(11) -0.79412(12) -0.35894(5) 0.0287(3) Uani 1 1 d . . . . .
N1 N 0.99242(13) -0.79027(12) -0.42611(6) 0.0196(3) Uani 1 1 d . . . . .
N2 N 0.85880(13) -0.65828(13) -0.55894(6) 0.0236(3) Uani 1 1 d . . . . .
C1 C 1.04431(15) -0.83029(15) -0.37568(7) 0.0212(4) Uani 1 1 d . . . . .
C13 C 1.05568(15) -0.70755(16) -0.52467(7) 0.0224(4) Uani 1 1 d . . . . .
H13 H 1.114584 -0.768556 -0.529429 0.027 Uiso 1 1 calc R U . . .
C14 C 1.03803(15) -0.68808(15) -0.45631(7) 0.0216(4) Uani 1 1 d . . . . .
H14A H 1.111741 -0.667163 -0.437360 0.026 Uiso 1 1 calc R U . . .
H14B H 0.984544 -0.623747 -0.450274 0.026 Uiso 1 1 calc R U . . .
C15 C 0.94565(16) -0.75019(16) -0.55493(7) 0.0226(4) Uani 1 1 d . . . . .
H15 H 0.964679 -0.775118 -0.597321 0.027 Uiso 1 1 calc R U . . .
C6 C 0.89862(15) -0.85389(15) -0.52017(8) 0.0226(4) Uani 1 1 d . . . . .
H6 H 0.956660 -0.916008 -0.523768 0.027 Uiso 1 1 calc R U . . .
C5 C 0.88224(15) -0.83012(15) -0.45135(7) 0.0210(4) Uani 1 1 d . . . . .
H5 H 0.825623 -0.766870 -0.446993 0.025 Uiso 1 1 calc R U . . .
C3 C 0.85622(17) -0.92210(17) -0.34921(8) 0.0296(4) Uani 1 1 d . . . . .
H3A H 0.821157 -0.850738 -0.334050 0.036 Uiso 1 1 calc R U . . .
H3B H 0.821244 -0.987112 -0.327318 0.036 Uiso 1 1 calc R U . . .
C4 C 0.83620(16) -0.93387(16) -0.41725(9) 0.0288(4) Uani 1 1 d . . . . .
H4A H 0.753470 -0.941664 -0.425210 0.035 Uiso 1 1 calc R U . . .
H4B H 0.874562 -1.003583 -0.432331 0.035 Uiso 1 1 calc R U . . .
C7 C 0.78964(17) -0.89674(17) -0.55149(9) 0.0312(5) Uani 1 1 d . . . . .
H7A H 0.808759 -0.926538 -0.592455 0.037 Uiso 1 1 calc R U . . .
H7B H 0.756451 -0.959931 -0.527381 0.037 Uiso 1 1 calc R U . . .
C2 C 0.98377(16) -0.92011(16) -0.33816(8) 0.0277(4) Uani 1 1 d . . . . .
H2A H 0.998179 -0.905422 -0.294393 0.033 Uiso 1 1 calc R U . . .
H2B H 1.015890 -0.995923 -0.348143 0.033 Uiso 1 1 calc R U . . .
C12 C 1.10106(17) -0.60023(17) -0.55568(8) 0.0284(4) Uani 1 1 d . . . . .
H12A H 1.130561 -0.620227 -0.596588 0.034 Uiso 1 1 calc R U . . .
H12B H 1.165130 -0.569011 -0.531487 0.034 Uiso 1 1 calc R U . . .
C8 C 0.70219(17) -0.80091(18) -0.55752(9) 0.0330(5) Uani 1 1 d . . . . .
H8A H 0.635136 -0.828530 -0.580627 0.040 Uiso 1 1 calc R U . . .
H8B H 0.676100 -0.777030 -0.516542 0.040 Uiso 1 1 calc R U . . .
C9 C 0.75516(17) -0.70001(19) -0.59037(9) 0.0331(5) Uani 1 1 d . . . . .
H9A H 0.775138 -0.722784 -0.632489 0.040 Uiso 1 1 calc R U . . .
H9B H 0.698672 -0.637436 -0.592811 0.040 Uiso 1 1 calc R U . . .
C11 C 1.00847(18) -0.50940(17) -0.56205(8) 0.0311(4) Uani 1 1 d . . . . .
H11A H 0.987483 -0.480124 -0.521231 0.037 Uiso 1 1 calc R U . . .
H11B H 1.037832 -0.444816 -0.586506 0.037 Uiso 1 1 calc R U . . .
C10 C 0.90406(17) -0.55942(17) -0.59279(8) 0.0311(4) Uani 1 1 d . . . . .
H10A H 0.844221 -0.500120 -0.595753 0.037 Uiso 1 1 calc R U . . .
H10B H 0.924239 -0.583401 -0.634691 0.037 Uiso 1 1 calc R U . . .
O2 O 0.75166(13) -0.53952(13) -0.46316(6) 0.0395(4) Uani 1 1 d D . . . .
H2C H 0.785985 -0.575458 -0.491082 0.059 Uiso 1 1 d DR U . . .
H2D H 0.716535 -0.591268 -0.441832 0.059 Uiso 1 1 d DR 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 C1 1.245(2) . ?
N1 C1 1.347(2) . ?
N1 C14 1.470(2) . ?
N1 C5 1.481(2) . ?
N2 C15 1.485(2) . ?
N2 C9 1.480(2) . ?
N2 C10 1.475(2) . ?
C1 C2 1.513(2) . ?
C13 H13 1.0000 . ?
C13 C14 1.531(2) . ?
C13 C15 1.535(3) . ?
C13 C12 1.526(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15 1.0000 . ?
C15 C6 1.538(3) . ?
C6 H6 1.0000 . ?
C6 C5 1.547(2) . ?
C6 C7 1.536(2) . ?
C5 H5 1.0000 . ?
C5 C4 1.527(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.517(3) . ?
C3 C2 1.515(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.527(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C11 1.527(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.518(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
O2 H2C 0.8454 . ?
O2 H2D 0.8700 . ?

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
C1 N1 C14 119.33(14) . . ?
C1 N1 C5 126.23(15) . . ?
C14 N1 C5 113.96(13) . . ?
C9 N2 C15 110.52(15) . . ?
C10 N2 C15 110.69(14) . . ?
C10 N2 C9 108.71(14) . . ?
O1 C1 N1 121.78(16) . . ?
O1 C1 C2 119.70(15) . . ?
N1 C1 C2 118.51(16) . . ?
C14 C13 H13 107.6 . . ?
C14 C13 C15 111.02(14) . . ?
C15 C13 H13 107.6 . . ?
C12 C13 H13 107.6 . . ?
C12 C13 C14 111.15(15) . . ?
C12 C13 C15 111.65(14) . . ?
N1 C14 C13 111.66(14) . . ?
N1 C14 H14A 109.3 . . ?
N1 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
N2 C15 C13 111.45(15) . . ?
N2 C15 H15 108.1 . . ?
N2 C15 C6 110.93(14) . . ?
C13 C15 H15 108.1 . . ?
C13 C15 C6 110.16(13) . . ?
C6 C15 H15 108.1 . . ?
C15 C6 H6 107.0 . . ?
C15 C6 C5 112.70(14) . . ?
C5 C6 H6 107.0 . . ?
C7 C6 C15 109.60(15) . . ?
C7 C6 H6 107.0 . . ?
C7 C6 C5 113.09(15) . . ?
N1 C5 C6 108.25(14) . . ?
N1 C5 H5 108.0 . . ?
N1 C5 C4 112.12(14) . . ?
C6 C5 H5 108.0 . . ?
C4 C5 C6 112.24(15) . . ?
C4 C5 H5 108.0 . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C2 C3 C4 108.15(15) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C3 C4 C5 110.78(15) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 110.91(15) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C1 C2 C3 112.75(15) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C13 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C13 C12 C11 111.58(15) . . ?
H12A C12 H12B 108.0 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.87(17) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
N2 C9 C8 111.87(15) . . ?
N2 C9 H9A 109.2 . . ?
N2 C9 H9B 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C10 C11 C12 110.19(16) . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
N2 C10 C11 111.76(15) . . ?
N2 C10 H10A 109.3 . . ?
N2 C10 H10B 109.3 . . ?
C11 C10 H10A 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
H2C O2 H2D 105.5 . . ?

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
O2 H2C N2 0.85 1.97 2.817(2) 177.0 . yes
O2 H2D O1 0.87 1.97 2.837(2) 178.1 5_434 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
O1 C1 C2 C3 157.86(17) . . . . ?
N1 C1 C2 C3 -21.0(2) . . . . ?
N1 C5 C4 C3 39.8(2) . . . . ?
N2 C15 C6 C5 -69.91(18) . . . . ?
N2 C15 C6 C7 56.97(18) . . . . ?
C1 N1 C14 C13 129.08(16) . . . . ?
C1 N1 C5 C6 -130.49(17) . . . . ?
C1 N1 C5 C4 -6.1(2) . . . . ?
C13 C15 C6 C5 53.97(18) . . . . ?
C13 C15 C6 C7 -179.15(14) . . . . ?
C13 C12 C11 C10 -52.7(2) . . . . ?
C14 N1 C1 O1 -10.9(2) . . . . ?
C14 N1 C1 C2 167.95(15) . . . . ?
C14 N1 C5 C6 57.59(18) . . . . ?
C14 N1 C5 C4 -178.07(15) . . . . ?
C14 C13 C15 N2 71.62(18) . . . . ?
C14 C13 C15 C6 -51.96(18) . . . . ?
C14 C13 C12 C11 -73.7(2) . . . . ?
C15 N2 C9 C8 59.31(19) . . . . ?
C15 N2 C10 C11 -60.31(19) . . . . ?
C15 C13 C14 N1 54.08(18) . . . . ?
C15 C13 C12 C11 50.8(2) . . . . ?
C15 C6 C5 N1 -55.37(18) . . . . ?
C15 C6 C5 C4 -179.65(14) . . . . ?
C15 C6 C7 C8 -55.1(2) . . . . ?
C6 C5 C4 C3 161.95(15) . . . . ?
C6 C7 C8 C9 54.9(2) . . . . ?
C5 N1 C1 O1 177.55(15) . . . . ?
C5 N1 C1 C2 -3.6(2) . . . . ?
C5 N1 C14 C13 -58.39(18) . . . . ?
C5 C6 C7 C8 71.6(2) . . . . ?
C4 C3 C2 C1 53.6(2) . . . . ?
C7 C6 C5 N1 179.62(14) . . . . ?
C7 C6 C5 C4 55.3(2) . . . . ?
C7 C8 C9 N2 -57.0(2) . . . . ?
C2 C3 C4 C5 -63.7(2) . . . . ?
C12 C13 C14 N1 179.01(14) . . . . ?
C12 C13 C15 N2 -53.02(18) . . . . ?
C12 C13 C15 C6 -176.60(14) . . . . ?
C12 C11 C10 N2 57.67(19) . . . . ?
C9 N2 C15 C13 177.84(13) . . . . ?
C9 N2 C15 C6 -59.02(17) . . . . ?
C9 N2 C10 C11 178.12(15) . . . . ?
C10 N2 C15 C13 57.34(17) . . . . ?
C10 N2 C15 C6 -179.52(14) . . . . ?
C10 N2 C9 C8 -179.02(16) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 60 electrons were 
found in a volume of 284Å³ in 1 void per unit cell. 
This is consistent with the presence of 
0.75[H2O] per Asymmetric Unit 
which account for 60 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.240 0.240 0.250 70.9 14.9 '1.5 H2O'
2 0.240 0.760 0.750 70.9 14.9 '1.5 H2O'
3 0.260 0.260 0.000 70.9 14.9 '1.5 H2O'
4 0.740 0.740 0.500 70.9 14.9 '1.5 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9(4)
2 0.1(4)

