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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_IMN
_database_code_depnum_ccdc_archive 'CCDC 2207949'
loop_
_audit_author_name
_audit_author_address
'Jiawei Lin'
;Tianjin University
China
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Isosorbide mononitrate'
_chemical_formula_moiety         'C6 H9 N O6'
_chemical_formula_sum            'C6 H9 N O6'
_chemical_formula_weight         191.14
_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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   15.86558(18)
_cell_length_b                   15.86558(18)
_cell_length_c                   6.49312(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1634.43(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11168
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      76.2690
_cell_measurement_theta_min      2.7730
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    1.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.63a (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    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15280
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.521
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -96.00 -67.00   0.50    1.00    --  -47.23 -17.00 111.00   58
  2  ω     55.00  80.00   0.50    1.00    --   47.23  17.00 -79.00   50
  3  ω     23.00  86.00   0.50    1.00    --   47.23-125.00  47.00  126
  4  ω   -149.00-117.00   0.50    4.00    -- -100.00 -17.00 111.00   64
  5  ω   -147.00-122.00   0.50    4.00    -- -100.00-125.00  47.00   50
  6  ω   -104.00 -42.00   0.50    4.00    -- -100.00 110.00  42.00  124
  7  ω     90.00 124.00   0.50    4.00    --  103.33-146.00-118.00   68
  8  ω    111.00 136.00   0.50    4.00    --  103.33  17.00 -79.00   50
  9  ω    111.00 137.00   0.50    4.00    --  103.33 146.00 -68.00   52
 10  ω    121.00 156.00   0.50    4.00    --  103.33 110.00  42.00   70
 11  ω   -117.00 -33.00   0.50    1.00    --  -47.23 -57.00 -30.00  168
 12  ω     33.00  70.00   0.50    1.00    --   47.23  57.00   0.00   74
 13  ω     44.00  69.00   0.50    1.00    --   47.23  19.00   0.00   50
 14  ω     29.00  56.00   0.50    1.00    --   47.23  77.00  30.00   54
 15  ω     41.00  67.00   0.50    1.00    --   47.23  37.00   0.00   52
 16  ω   -116.00 -82.00   0.50    4.00    -- -100.00 -69.00  -7.91   68
 17  ω   -167.00 -82.00   0.50    4.00    -- -100.00 -68.00  13.99  170
 18  ω   -105.00 -80.00   0.50    4.00    -- -100.00 -74.00   5.05   50
 19  ω   -172.00 -82.00   0.50    4.00    -- -100.00 -68.00   8.48  180
 20  ω   -106.00 -80.00   0.50    4.00    -- -100.00 -74.00  33.48   52
 21  ω   -105.00 -79.00   0.50    4.00    -- -100.00 -77.00  30.00   52
 22  ω   -132.00 -82.00   0.50    4.00    -- -100.00 -67.00  30.65  100
 23  ω   -113.00 -80.00   0.50    4.00    -- -100.00 -77.00  60.00   66
 24  ω   -107.00 -82.00   0.50    4.00    -- -100.00 -73.00  10.99   50
 25  ω   -112.00 -81.00   0.50    4.00    -- -100.00 -74.00  47.96   62
 26  ω   -172.00 -80.00   0.50    4.00    -- -100.00 -81.00  78.61  184
 27  ω   -103.00 -78.00   0.50    4.00    -- -100.00 -77.00   0.00   50
 28  ω   -107.00 -82.00   0.50    4.00    -- -100.00 -70.00 -13.26   50
 29  ω   -154.00 -80.00   0.50    4.00    -- -100.00 -73.00  27.80  148
 30  ω     49.00  74.00   0.50    4.00    --  103.33 -61.00 -60.00   50
 31  ω     34.00  66.00   0.50    4.00    --  103.33 -61.00   0.00   64
 32  ω     36.00  74.00   0.50    4.00    --  103.33 -61.00  90.00   76
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0948155000
_diffrn_orient_matrix_UB_12      0.0064672000
_diffrn_orient_matrix_UB_13      -0.0482077000
_diffrn_orient_matrix_UB_21      0.0077644000
_diffrn_orient_matrix_UB_22      0.0966118000
_diffrn_orient_matrix_UB_23      -0.0142819000
_diffrn_orient_matrix_UB_31      0.0191672000
_diffrn_orient_matrix_UB_32      -0.0072725000
_diffrn_orient_matrix_UB_33      -0.2320136000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.943
_reflns_Friedel_fraction_max     0.868
_reflns_number_gt                3034
_reflns_number_total             3159
_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 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.63a (Rigaku OD, 2022)'
_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    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0277
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.068
_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)+(0.0385P)²+0.1723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23), C1(H1), C3(H3), C5(H5), C7(H7), C9(H9), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C35(H35A,H35B), C15(H15A,H15B), C18(H18A,H18B)
2.c Idealised tetrahedral OH refined as rotating group:
 O33(H33)
;
_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
O28 O 0.78010(8) 0.09921(8) 0.1383(2) 0.0293(3) Uani 1 1 d . . . . .
O29 O 0.76376(8) 0.46831(8) 0.1965(2) 0.0319(3) Uani 1 1 d . . . . .
O25 O 0.66863(8) 0.18971(8) 0.3459(2) 0.0304(3) Uani 1 1 d . . . . .
O26 O 0.82504(9) 0.17711(9) 0.5880(2) 0.0342(3) Uani 1 1 d . . . . .
O33 O 0.96012(8) 0.08403(9) 0.1961(3) 0.0348(3) Uani 1 1 d . . . . .
H33 H 0.997223 0.070705 0.282448 0.052 Uiso 1 1 calc R U . . .
O24 O 0.88781(9) 0.37587(9) 0.3630(2) 0.0350(3) Uani 1 1 d . . . . .
O41 O 0.73888(9) 0.36658(9) 0.6321(2) 0.0361(3) Uani 1 1 d . . . . .
O27 O 0.59972(9) 0.09578(10) 0.1519(3) 0.0438(4) Uani 1 1 d . . . . .
O34 O 0.58001(10) 0.45613(10) 0.3003(3) 0.0439(4) Uani 1 1 d . . . . .
O30 O 0.95279(10) 0.48248(11) 0.2024(3) 0.0484(4) Uani 1 1 d . . . . .
O39 O 0.60843(11) 0.22716(11) 0.0602(3) 0.0465(4) Uani 1 1 d . . . . .
N22 N 0.62171(10) 0.16752(12) 0.1711(3) 0.0346(4) Uani 1 1 d . . . . .
O37 O 0.95488(11) 0.35501(13) 0.0772(3) 0.0532(5) Uani 1 1 d . . . . .
N38 N 0.93562(10) 0.40886(13) 0.2007(3) 0.0388(4) Uani 1 1 d . . . . .
C43 C 0.84003(12) 0.16726(12) 0.1247(3) 0.0297(4) Uani 1 1 d . . . . .
H43A H 0.812775 0.221858 0.156486 0.036 Uiso 1 1 calc R U . . .
H43B H 0.864872 0.170247 -0.014982 0.036 Uiso 1 1 calc R U . . .
C35 C 0.70841(12) 0.39719(13) 0.1698(3) 0.0331(4) Uani 1 1 d . . . . .
H35A H 0.740777 0.343846 0.171996 0.040 Uiso 1 1 calc R U . . .
H35B H 0.677967 0.401224 0.037033 0.040 Uiso 1 1 calc R U . . .
C23 C 0.64726(12) 0.40055(12) 0.3482(3) 0.0309(4) Uani 1 1 d . . . . .
H23 H 0.625677 0.343034 0.382607 0.037 Uiso 1 1 calc R U . . .
C1 C 0.77402(12) 0.07565(12) 0.3483(3) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.770951 0.012957 0.362330 0.035 Uiso 1 1 calc R U . . .
C3 C 0.69949(12) 0.11841(12) 0.4636(3) 0.0310(4) Uani 1 1 d . . . . .
H3 H 0.653728 0.077655 0.499668 0.037 Uiso 1 1 calc R U . . .
C5 C 0.90641(12) 0.14665(12) 0.2821(3) 0.0304(4) Uani 1 1 d . . . . .
H5 H 0.938519 0.197836 0.325927 0.036 Uiso 1 1 calc R U . . .
C7 C 0.70172(13) 0.43516(13) 0.5215(3) 0.0329(4) Uani 1 1 d . . . . .
H7 H 0.669354 0.473692 0.614264 0.039 Uiso 1 1 calc R U . . .
C9 C 0.77470(12) 0.48126(12) 0.4113(3) 0.0308(4) Uani 1 1 d . . . . .
H9 H 0.773490 0.542819 0.444186 0.037 Uiso 1 1 calc R U . . .
C11 C 0.85342(12) 0.11046(12) 0.4576(3) 0.0316(4) Uani 1 1 d . . . . .
H11 H 0.884183 0.065760 0.535911 0.038 Uiso 1 1 calc R U . . .
C13 C 0.85513(13) 0.43973(13) 0.5022(3) 0.0345(5) Uani 1 1 d . . . . .
H13 H 0.898856 0.482248 0.541105 0.041 Uiso 1 1 calc R U . . .
C15 C 0.74144(13) 0.15571(14) 0.6520(3) 0.0361(4) Uani 1 1 d . . . . .
H15A H 0.710759 0.206478 0.699346 0.043 Uiso 1 1 calc R U . . .
H15B H 0.742902 0.114160 0.765726 0.043 Uiso 1 1 calc R U . . .
C18 C 0.82232(13) 0.39160(15) 0.6863(4) 0.0389(5) Uani 1 1 d . . . . .
H18A H 0.857964 0.341680 0.714385 0.047 Uiso 1 1 calc R U . . .
H18B H 0.821666 0.427906 0.810337 0.047 Uiso 1 1 calc R U . . .
H34 H 0.5378(18) 0.4420(17) 0.378(5) 0.047(7) 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
O28 C43 1.441(2) . ?
O28 C1 1.418(3) . ?
O29 C35 1.440(2) . ?
O29 C9 1.420(3) . ?
O25 N22 1.402(2) . ?
O25 C3 1.450(2) . ?
O26 C11 1.428(2) . ?
O26 C15 1.431(3) . ?
O33 H33 0.8400 . ?
O33 C5 1.423(2) . ?
O24 N38 1.400(2) . ?
O24 C13 1.453(3) . ?
O41 C7 1.431(2) . ?
O41 C18 1.426(3) . ?
O27 N22 1.197(2) . ?
O34 C23 1.419(2) . ?
O34 H34 0.87(3) . ?
O30 N38 1.199(3) . ?
O39 N22 1.208(3) . ?
O37 N38 1.211(3) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C5 1.504(3) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C23 1.512(3) . ?
C23 H23 1.0000 . ?
C23 C7 1.521(3) . ?
C1 H1 1.0000 . ?
C1 C3 1.555(3) . ?
C1 C11 1.548(3) . ?
C3 H3 1.0000 . ?
C3 C15 1.513(3) . ?
C5 H5 1.0000 . ?
C5 C11 1.528(3) . ?
C7 H7 1.0000 . ?
C7 C9 1.545(3) . ?
C9 H9 1.0000 . ?
C9 C13 1.553(3) . ?
C11 H11 1.0000 . ?
C13 H13 1.0000 . ?
C13 C18 1.511(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 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
C1 O28 C43 107.53(15) . . ?
C9 O29 C35 107.83(15) . . ?
N22 O25 C3 114.19(14) . . ?
C11 O26 C15 106.79(15) . . ?
C5 O33 H33 109.5 . . ?
N38 O24 C13 113.62(15) . . ?
C18 O41 C7 107.14(16) . . ?
C23 O34 H34 107.0(19) . . ?
O27 N22 O25 118.56(18) . . ?
O27 N22 O39 129.17(19) . . ?
O39 N22 O25 112.26(16) . . ?
O30 N38 O24 118.7(2) . . ?
O30 N38 O37 129.5(2) . . ?
O37 N38 O24 111.82(19) . . ?
O28 C43 H43A 110.8 . . ?
O28 C43 H43B 110.8 . . ?
O28 C43 C5 104.93(15) . . ?
H43A C43 H43B 108.8 . . ?
C5 C43 H43A 110.8 . . ?
C5 C43 H43B 110.8 . . ?
O29 C35 H35A 110.6 . . ?
O29 C35 H35B 110.6 . . ?
O29 C35 C23 105.73(17) . . ?
H35A C35 H35B 108.7 . . ?
C23 C35 H35A 110.6 . . ?
C23 C35 H35B 110.6 . . ?
O34 C23 C35 109.67(17) . . ?
O34 C23 H23 111.0 . . ?
O34 C23 C7 111.40(17) . . ?
C35 C23 H23 111.0 . . ?
C35 C23 C7 102.43(15) . . ?
C7 C23 H23 111.0 . . ?
O28 C1 H1 110.7 . . ?
O28 C1 C3 113.56(16) . . ?
O28 C1 C11 106.95(16) . . ?
C3 C1 H1 110.7 . . ?
C11 C1 H1 110.7 . . ?
C11 C1 C3 104.05(15) . . ?
O25 C3 C1 110.09(16) . . ?
O25 C3 H3 112.5 . . ?
O25 C3 C15 105.62(15) . . ?
C1 C3 H3 112.5 . . ?
C15 C3 C1 103.01(16) . . ?
C15 C3 H3 112.5 . . ?
O33 C5 C43 107.72(16) . . ?
O33 C5 H5 111.9 . . ?
O33 C5 C11 111.09(16) . . ?
C43 C5 H5 111.9 . . ?
C43 C5 C11 101.73(16) . . ?
C11 C5 H5 111.9 . . ?
O41 C7 C23 109.32(16) . . ?
O41 C7 H7 112.0 . . ?
O41 C7 C9 106.48(15) . . ?
C23 C7 H7 112.0 . . ?
C23 C7 C9 104.69(16) . . ?
C9 C7 H7 112.0 . . ?
O29 C9 C7 107.15(16) . . ?
O29 C9 H9 110.4 . . ?
O29 C9 C13 114.35(16) . . ?
C7 C9 H9 110.4 . . ?
C7 C9 C13 103.81(16) . . ?
C13 C9 H9 110.4 . . ?
O26 C11 C1 106.24(15) . . ?
O26 C11 C5 109.73(15) . . ?
O26 C11 H11 112.2 . . ?
C1 C11 H11 112.2 . . ?
C5 C11 C1 103.90(16) . . ?
C5 C11 H11 112.2 . . ?
O24 C13 C9 110.64(16) . . ?
O24 C13 H13 112.3 . . ?
O24 C13 C18 105.22(16) . . ?
C9 C13 H13 112.3 . . ?
C18 C13 C9 103.42(17) . . ?
C18 C13 H13 112.3 . . ?
O26 C15 C3 105.41(17) . . ?
O26 C15 H15A 110.7 . . ?
O26 C15 H15B 110.7 . . ?
C3 C15 H15A 110.7 . . ?
C3 C15 H15B 110.7 . . ?
H15A C15 H15B 108.8 . . ?
O41 C18 C13 105.37(17) . . ?
O41 C18 H18A 110.7 . . ?
O41 C18 H18B 110.7 . . ?
C13 C18 H18A 110.7 . . ?
C13 C18 H18B 110.7 . . ?
H18A C18 H18B 108.8 . . ?

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
O28 C43 C5 O33 78.58(19) . . . . ?
O28 C43 C5 C11 -38.30(18) . . . . ?
O28 C1 C3 O25 -16.2(2) . . . . ?
O28 C1 C3 C15 -128.42(17) . . . . ?
O28 C1 C11 O26 110.10(17) . . . . ?
O28 C1 C11 C5 -5.65(18) . . . . ?
O29 C35 C23 O34 84.1(2) . . . . ?
O29 C35 C23 C7 -34.30(19) . . . . ?
O29 C9 C13 O24 -17.5(2) . . . . ?
O29 C9 C13 C18 -129.69(18) . . . . ?
O25 C3 C15 O26 -84.02(18) . . . . ?
O33 C5 C11 O26 158.53(15) . . . . ?
O33 C5 C11 C1 -88.22(17) . . . . ?
O24 C13 C18 O41 -84.7(2) . . . . ?
O41 C7 C9 O29 112.42(17) . . . . ?
O41 C7 C9 C13 -8.9(2) . . . . ?
O34 C23 C7 O41 151.46(16) . . . . ?
O34 C23 C7 C9 -94.79(18) . . . . ?
N22 O25 C3 C1 74.00(18) . . . . ?
N22 O25 C3 C15 -175.43(15) . . . . ?
N38 O24 C13 C9 80.55(19) . . . . ?
N38 O24 C13 C18 -168.37(15) . . . . ?
C43 O28 C1 C3 95.51(17) . . . . ?
C43 O28 C1 C11 -18.68(18) . . . . ?
C43 C5 C11 O26 -87.07(18) . . . . ?
C43 C5 C11 C1 26.18(18) . . . . ?
C35 O29 C9 C7 -18.61(19) . . . . ?
C35 O29 C9 C13 95.84(18) . . . . ?
C35 C23 C7 O41 -91.37(18) . . . . ?
C35 C23 C7 C9 22.37(19) . . . . ?
C23 C7 C9 O29 -3.3(2) . . . . ?
C23 C7 C9 C13 -124.67(16) . . . . ?
C1 O28 C43 C5 36.42(19) . . . . ?
C1 C3 C15 O26 31.5(2) . . . . ?
C3 O25 N22 O27 11.8(2) . . . . ?
C3 O25 N22 O39 -169.12(17) . . . . ?
C3 C1 C11 O26 -10.4(2) . . . . ?
C3 C1 C11 C5 -126.11(16) . . . . ?
C7 O41 C18 C13 -38.9(2) . . . . ?
C7 C9 C13 O24 98.94(18) . . . . ?
C7 C9 C13 C18 -13.3(2) . . . . ?
C9 O29 C35 C23 33.72(19) . . . . ?
C9 C13 C18 O41 31.4(2) . . . . ?
C11 O26 C15 C3 -40.0(2) . . . . ?
C11 C1 C3 O25 99.76(17) . . . . ?
C11 C1 C3 C15 -12.50(19) . . . . ?
C13 O24 N38 O30 7.9(2) . . . . ?
C13 O24 N38 O37 -173.30(17) . . . . ?
C15 O26 C11 C1 31.1(2) . . . . ?
C15 O26 C11 C5 142.85(16) . . . . ?
C18 O41 C7 C23 142.22(17) . . . . ?
C18 O41 C7 C9 29.6(2) . . . . ?

_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.789
_oxdiff_exptl_absorpt_empirical_full_min 0.570
####################################################################### 
# 
# 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_IMN_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2207955'
loop_
_audit_author_name
_audit_author_address
'Jiawei Lin'
;Tianjin University
China
;
_audit_update_record             
;
2022-09-18 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Isosorbide mononitrate'
_chemical_formula_moiety         'C6 H9 N O6'
_chemical_formula_sum            'C6 H9 N O6'
_chemical_formula_weight         191.14
_chemical_absolute_configuration rm
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           76
_space_group_name_H-M_alt        'P 41'
_space_group_name_Hall           'P 4w'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+1/4'
'y, -x, z+3/4'

_cell_length_a                   15.8980(6)
_cell_length_b                   15.8980(6)
_cell_length_c                   6.4937(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1641.26(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7010
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      30.9690
_cell_measurement_theta_min      1.8130
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78762
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            14602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         1.812
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   1.00    4.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  35.00   1.00    4.00    --  -25.00  45.00  90.00  150
  3  ω   -115.00   5.00   1.00    4.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0186146000
_diffrn_orient_matrix_UB_12      0.0405542000
_diffrn_orient_matrix_UB_13      -0.0015180000
_diffrn_orient_matrix_UB_21      -0.0405135000
_diffrn_orient_matrix_UB_22      -0.0185422000
_diffrn_orient_matrix_UB_23      0.0060243000
_diffrn_orient_matrix_UB_31      0.0019784000
_diffrn_orient_matrix_UB_32      0.0015832000
_diffrn_orient_matrix_UB_33      0.1090072000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2673
_reflns_number_total             3359
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_refine_ls_extinction_coef       0.0144(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      1.081
_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)+(0.0353P)²+0.3849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C6(H6A), C7(H7), C9(H9), C10(H10), C12(H12A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C11(H11A,H11B)
2.c Idealised tetrahedral OH refined as rotating group:
 O6(H6), O12(H12)
;
_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
O1 O 0.7726(2) 0.39145(19) 0.0603(5) 0.0417(8) Uani 1 1 d . . . . .
O2 O 0.90443(19) 0.40004(18) 0.1518(5) 0.0398(8) Uani 1 1 d . . . . .
O3 O 0.80990(16) 0.33113(16) 0.3457(4) 0.0260(6) Uani 1 1 d . . . . .
O4 O 0.82270(17) 0.17473(17) 0.5881(4) 0.0303(7) Uani 1 1 d . . . . .
O5 O 0.90057(16) 0.21992(16) 0.1378(4) 0.0262(6) Uani 1 1 d . . . . .
O6 O 0.91574(17) 0.03896(16) 0.1980(5) 0.0316(7) Uani 1 1 d . . . . .
H6 H 0.950871 0.067419 0.131078 0.047 Uiso 1 1 calc R U . . .
N1 N 0.8320(2) 0.3780(2) 0.1698(6) 0.0311(8) Uani 1 1 d . . . . .
C1 C 0.8814(2) 0.3003(2) 0.4641(7) 0.0268(9) Uani 1 1 d . . . . .
H1 H 0.922066 0.345958 0.500184 0.032 Uiso 1 1 calc R U . . .
C2 C 0.8441(3) 0.2588(2) 0.6512(7) 0.0310(9) Uani 1 1 d . . . . .
H2A H 0.885398 0.257620 0.765286 0.037 Uiso 1 1 calc R U . . .
H2B H 0.793368 0.289506 0.697763 0.037 Uiso 1 1 calc R U . . .
C3 C 0.8894(2) 0.1465(2) 0.4568(7) 0.0285(9) Uani 1 1 d . . . . .
H3 H 0.934148 0.115841 0.534998 0.034 Uiso 1 1 calc R U . . .
C4 C 0.9238(2) 0.2260(2) 0.3490(6) 0.0263(9) Uani 1 1 d . . . . .
H4 H 0.986381 0.229094 0.363136 0.032 Uiso 1 1 calc R U . . .
C5 C 0.8326(2) 0.1597(2) 0.1252(7) 0.0259(9) Uani 1 1 d . . . . .
H5A H 0.829434 0.134775 -0.014357 0.031 Uiso 1 1 calc R U . . .
H5B H 0.778044 0.186760 0.157261 0.031 Uiso 1 1 calc R U . . .
C6 C 0.8533(2) 0.0936(2) 0.2825(7) 0.0268(9) Uani 1 1 d . . . . .
H6A H 0.802121 0.061856 0.326981 0.032 Uiso 1 1 calc R U . . .
O7 O 0.9553(2) 0.6448(2) 0.3260(5) 0.0487(9) Uani 1 1 d . . . . .
O8 O 0.95296(18) 0.5170(2) 0.4510(6) 0.0439(9) Uani 1 1 d . . . . .
O9 O 0.88805(16) 0.62404(17) 0.6125(5) 0.0316(7) Uani 1 1 d . . . . .
O10 O 0.73901(17) 0.63321(17) 0.8816(5) 0.0317(7) Uani 1 1 d . . . . .
O11 O 0.76418(16) 0.53143(16) 0.4455(4) 0.0284(6) Uani 1 1 d . . . . .
O12 O 0.58021(17) 0.54352(19) 0.5494(5) 0.0394(8) Uani 1 1 d . . . . .
H12 H 0.537306 0.557269 0.617008 0.059 Uiso 1 1 calc R U . . .
N2 N 0.9359(2) 0.5911(3) 0.4499(6) 0.0364(9) Uani 1 1 d . . . . .
C7 C 0.8553(3) 0.5602(3) 0.7530(7) 0.0309(10) Uani 1 1 d . . . . .
H7 H 0.898886 0.517808 0.792341 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8225(3) 0.6081(3) 0.9355(7) 0.0344(10) Uani 1 1 d . . . . .
H8A H 0.821810 0.571929 1.059600 0.041 Uiso 1 1 calc R U . . .
H8B H 0.858054 0.657895 0.963430 0.041 Uiso 1 1 calc R U . . .
C9 C 0.7018(2) 0.5645(2) 0.7711(7) 0.0281(9) Uani 1 1 d . . . . .
H9 H 0.669357 0.526121 0.863655 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7749(2) 0.5186(2) 0.6616(6) 0.0267(9) Uani 1 1 d . . . . .
H10 H 0.773760 0.457195 0.694667 0.032 Uiso 1 1 calc R U . . .
C11 C 0.7083(2) 0.6025(2) 0.4188(7) 0.0297(9) Uani 1 1 d . . . . .
H11A H 0.677638 0.598077 0.286589 0.036 Uiso 1 1 calc R U . . .
H11B H 0.740450 0.655820 0.419860 0.036 Uiso 1 1 calc R U . . .
C12 C 0.6477(2) 0.5995(2) 0.5977(7) 0.0278(9) Uani 1 1 d . . . . .
H12A H 0.626274 0.656902 0.632191 0.033 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 N1 1.201(5) . ?
O2 N1 1.210(4) . ?
O3 N1 1.408(4) . ?
O3 C1 1.457(5) . ?
O4 C2 1.439(5) . ?
O4 C3 1.433(5) . ?
O5 C4 1.423(5) . ?
O5 C5 1.447(4) . ?
O6 H6 0.8400 . ?
O6 C6 1.428(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.504(6) . ?
C1 C4 1.552(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C4 1.546(5) . ?
C3 C6 1.523(6) . ?
C4 H4 1.0000 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.502(6) . ?
C6 H6A 1.0000 . ?
O7 N2 1.212(5) . ?
O8 N2 1.209(5) . ?
O9 N2 1.403(5) . ?
O9 C7 1.461(5) . ?
O10 C8 1.429(5) . ?
O10 C9 1.435(5) . ?
O11 C10 1.428(5) . ?
O11 C11 1.447(4) . ?
O12 H12 0.8400 . ?
O12 C12 1.429(4) . ?
C7 H7 1.0000 . ?
C7 C8 1.502(6) . ?
C7 C10 1.556(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.546(5) . ?
C9 C12 1.521(6) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(6) . ?
C12 H12A 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O3 C1 114.3(3) . . ?
C3 O4 C2 106.6(3) . . ?
C4 O5 C5 107.1(3) . . ?
C6 O6 H6 109.5 . . ?
O1 N1 O2 129.8(4) . . ?
O1 N1 O3 112.3(3) . . ?
O2 N1 O3 118.0(3) . . ?
O3 C1 H1 112.6 . . ?
O3 C1 C2 105.5(3) . . ?
O3 C1 C4 109.9(3) . . ?
C2 C1 H1 112.6 . . ?
C2 C1 C4 103.1(3) . . ?
C4 C1 H1 112.6 . . ?
O4 C2 C1 105.7(3) . . ?
O4 C2 H2A 110.6 . . ?
O4 C2 H2B 110.6 . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
O4 C3 H3 112.1 . . ?
O4 C3 C4 105.9(3) . . ?
O4 C3 C6 109.7(3) . . ?
C4 C3 H3 112.1 . . ?
C6 C3 H3 112.1 . . ?
C6 C3 C4 104.4(3) . . ?
O5 C4 C1 113.7(3) . . ?
O5 C4 C3 106.8(3) . . ?
O5 C4 H4 110.5 . . ?
C1 C4 H4 110.5 . . ?
C3 C4 C1 104.5(3) . . ?
C3 C4 H4 110.5 . . ?
O5 C5 H5A 110.7 . . ?
O5 C5 H5B 110.7 . . ?
O5 C5 C6 105.1(3) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
O6 C6 C3 111.1(3) . . ?
O6 C6 C5 108.5(3) . . ?
O6 C6 H6A 111.7 . . ?
C3 C6 H6A 111.7 . . ?
C5 C6 C3 101.7(3) . . ?
C5 C6 H6A 111.7 . . ?
N2 O9 C7 113.8(3) . . ?
C8 O10 C9 107.0(3) . . ?
C10 O11 C11 107.6(3) . . ?
C12 O12 H12 109.5 . . ?
O7 N2 O9 112.0(4) . . ?
O8 N2 O7 129.2(4) . . ?
O8 N2 O9 118.8(4) . . ?
O9 C7 H7 112.4 . . ?
O9 C7 C8 105.3(3) . . ?
O9 C7 C10 110.5(3) . . ?
C8 C7 H7 112.4 . . ?
C8 C7 C10 103.4(3) . . ?
C10 C7 H7 112.4 . . ?
O10 C8 C7 105.7(3) . . ?
O10 C8 H8A 110.6 . . ?
O10 C8 H8B 110.6 . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
O10 C9 H9 112.1 . . ?
O10 C9 C10 106.2(3) . . ?
O10 C9 C12 108.9(3) . . ?
C10 C9 H9 112.1 . . ?
C12 C9 H9 112.1 . . ?
C12 C9 C10 104.9(3) . . ?
O11 C10 C7 114.4(3) . . ?
O11 C10 C9 107.1(3) . . ?
O11 C10 H10 110.4 . . ?
C7 C10 H10 110.4 . . ?
C9 C10 C7 104.0(3) . . ?
C9 C10 H10 110.4 . . ?
O11 C11 H11A 110.5 . . ?
O11 C11 H11B 110.5 . . ?
O11 C11 C12 105.9(3) . . ?
H11A C11 H11B 108.7 . . ?
C12 C11 H11A 110.5 . . ?
C12 C11 H11B 110.5 . . ?
O12 C12 C9 111.1(3) . . ?
O12 C12 C11 109.3(3) . . ?
O12 C12 H12A 111.2 . . ?
C9 C12 H12A 111.2 . . ?
C11 C12 C9 102.7(3) . . ?
C11 C12 H12A 111.2 . . ?

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 C1 C2 O4 84.2(4) . . . . ?
O3 C1 C4 O5 16.4(4) . . . . ?
O3 C1 C4 C3 -99.7(3) . . . . ?
O4 C3 C4 O5 -110.5(3) . . . . ?
O4 C3 C4 C1 10.3(4) . . . . ?
O4 C3 C6 O6 -157.6(3) . . . . ?
O4 C3 C6 C5 87.2(3) . . . . ?
O5 C5 C6 O6 -78.8(4) . . . . ?
O5 C5 C6 C3 38.3(4) . . . . ?
N1 O3 C1 C2 175.5(3) . . . . ?
N1 O3 C1 C4 -74.0(4) . . . . ?
C1 O3 N1 O1 169.5(3) . . . . ?
C1 O3 N1 O2 -12.0(4) . . . . ?
C2 O4 C3 C4 -30.6(4) . . . . ?
C2 O4 C3 C6 -142.7(3) . . . . ?
C2 C1 C4 O5 128.5(3) . . . . ?
C2 C1 C4 C3 12.4(4) . . . . ?
C3 O4 C2 C1 39.5(4) . . . . ?
C4 O5 C5 C6 -36.6(4) . . . . ?
C4 C1 C2 O4 -31.1(4) . . . . ?
C4 C3 C6 O6 89.3(4) . . . . ?
C4 C3 C6 C5 -26.0(4) . . . . ?
C5 O5 C4 C1 -95.8(4) . . . . ?
C5 O5 C4 C3 19.0(4) . . . . ?
C6 C3 C4 O5 5.2(4) . . . . ?
C6 C3 C4 C1 126.1(3) . . . . ?
O9 C7 C8 O10 84.6(4) . . . . ?
O9 C7 C10 O11 17.4(4) . . . . ?
O9 C7 C10 C9 -99.0(4) . . . . ?
O10 C9 C10 O11 -112.4(3) . . . . ?
O10 C9 C10 C7 9.0(4) . . . . ?
O10 C9 C12 O12 -151.7(3) . . . . ?
O10 C9 C12 C11 91.6(4) . . . . ?
O11 C11 C12 O12 -84.4(4) . . . . ?
O11 C11 C12 C9 33.6(4) . . . . ?
N2 O9 C7 C8 168.6(3) . . . . ?
N2 O9 C7 C10 -80.5(4) . . . . ?
C7 O9 N2 O7 173.4(3) . . . . ?
C7 O9 N2 O8 -7.5(5) . . . . ?
C8 O10 C9 C10 -29.5(4) . . . . ?
C8 O10 C9 C12 -142.0(3) . . . . ?
C8 C7 C10 O11 129.7(3) . . . . ?
C8 C7 C10 C9 13.2(4) . . . . ?
C9 O10 C8 C7 38.9(4) . . . . ?
C10 O11 C11 C12 -33.2(4) . . . . ?
C10 C7 C8 O10 -31.4(4) . . . . ?
C10 C9 C12 O12 95.0(4) . . . . ?
C10 C9 C12 C11 -21.8(4) . . . . ?
C11 O11 C10 C7 -96.2(4) . . . . ?
C11 O11 C10 C9 18.5(4) . . . . ?
C12 C9 C10 O11 2.9(4) . . . . ?
C12 C9 C10 C7 124.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.525
_oxdiff_exptl_absorpt_empirical_full_min 0.522
