# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_C6BMTT
_database_code_depnum_ccdc_archive 'CCDC 2270301'
loop_
_audit_author_name
_audit_author_address
'Aida Ildusovna Samigullina'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-01-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H20 N4 O4, H2 O'
_chemical_formula_sum            'C22 H22 N4 O5'
_chemical_formula_weight         422.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N4O4
_chemical_oxdiff_usercomment     C6BMTT
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.26940(12)
_cell_length_b                   11.01204(19)
_cell_length_c                   12.41759(17)
_cell_angle_alpha                66.2311(15)
_cell_angle_beta                 74.6710(13)
_cell_angle_gamma                76.7962(14)
_cell_volume                     988.49(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    31007
_cell_measurement_temperature    99.95(16)
_cell_measurement_theta_max      77.4960
_cell_measurement_theta_min      3.9340
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.835
_exptl_absorpt_coefficient_mu    0.851
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rhombic
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 1 0.0526
0 -1 -1 0.0620
0 -1 0 0.0110
0 1 0 0.0103
1 1 1 0.0554
-1 -1 -1 0.0401

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0007 0.9996 0.9988 -0.1070 0.0053 0.1259
0.0007 -0.9996 -0.9988 0.1070 -0.0053 -0.1259
0.0009 -0.9993 0.0005 0.1461 0.0493 -0.0053
-0.0009 0.9993 -0.0005 -0.1461 -0.0493 0.0053
0.9986 1.0000 0.9986 -0.1364 0.1660 0.0197
-0.9986 -1.0000 -0.9986 0.1364 -0.1660 -0.0197

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0121
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            47219
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.859
_diffrn_reflns_theta_min         3.965
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -121.00 -39.00   0.50    0.41    --  -48.70 -38.00 156.00  164
  2  ω     39.00 121.00   0.50    0.41    --   48.70  38.00 -48.00  164
  3  ω    -23.00  43.00   0.50    0.41    --   48.70 -38.00 156.00  132
  4  ω    -43.00 -14.00   0.50    1.64    --  -86.25  38.00 -48.00   58
  5  ω   -158.00 -75.00   0.50    1.64    --  -86.25 -38.00 156.00  166
  6  ω     97.00 178.00   0.50    1.64    --  107.75  38.00 -48.00  162
  7  ω    -42.00 -12.00   0.50    0.41    --    2.00 124.00 151.79   60
  8  ω     -9.00  43.00   0.50    0.41    --   18.00  89.00  -0.29  104
  9  ω     -1.00  43.00   0.50    0.41    --   26.00  89.00  52.07   88
 10  ω      4.00  31.00   0.50    0.41    --   34.00  95.00 177.27   54
 11  ω    -86.00 -13.00   0.50    0.41    --  -48.70 125.00 120.00  146
 12  ω    -43.00  24.00   0.50    0.41    --  -48.70  38.00 -48.00  134
 13  ω     27.00 120.00   0.50    0.41    --   48.70  77.00 -90.00  186
 14  ω     27.00 120.00   0.50    0.41    --   48.70  77.00-150.00  186
 15  ω    -25.00  26.00   0.50    0.41    --   48.70 -19.00 -90.00  102
 16  ω     34.00  93.00   0.50    0.41    --   48.70-125.00   0.00  118
 17  ω     27.00 120.00   0.50    0.41    --   48.70  77.00 -30.00  186
 18  ω   -121.00 -28.00   0.50    0.41    --  -50.00 -77.00  86.49  186
 19  ω     28.00 121.00   0.50    0.41    --   50.00  77.00  33.52  186
 20  ω     30.00 121.00   0.50    0.41    --   50.00  74.00 -46.99  182
 21  ω   -125.00 -33.00   0.50    0.41    --  -54.00 -75.00 154.79  184
 22  ω     34.00 125.00   0.50    0.41    --   54.00  74.00  90.54  182
 23  ω     34.00 125.00   0.50    0.41    --   54.00  74.00  66.38  182
 24  ω     37.00 130.00   0.50    0.41    --   58.00  75.00 177.03  186
 25  ω     38.00 130.00   0.50    0.41    --   58.00  72.00-129.06  184
 26  ω     38.00 130.00   0.50    0.41    --   58.00  74.00 138.39  184
 27  ω     42.00 134.00   0.50    0.41    --   62.00  72.00  10.39  184
 28  ω     41.00 134.00   0.50    0.41    --   62.00  76.00 179.68  186
 29  ω     42.00 134.00   0.50    0.41    --   62.00  73.00 -19.59  184
 30  ω   -138.00 -49.00   0.50    0.41    --  -66.00 -66.00  85.25  178
 31  ω   -138.00 -47.00   0.50    0.41    --  -66.00 -70.00-129.58  182
 32  ω     45.00 138.00   0.50    0.41    --   66.00  75.00  33.40  186
 33  ω     44.00 138.00   0.50    0.41    --   66.00  77.00-129.29  188
 34  ω   -142.00 -53.00   0.50    1.64    --  -70.00 -65.00 -78.08  178
 35  ω     49.00 142.00   0.50    0.41    --   70.00  76.00  68.97  186
 36  ω   -142.00 -53.00   0.50    1.64    --  -70.00 -66.00-114.72  178
 37  ω   -142.00 -52.00   0.50    1.64    --  -70.00 -67.00 -54.21  180
 38  ω   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 -96.54  176
 39  ω   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 -84.06  176
 40  ω   -145.00 -57.00   0.50    1.64    --  -74.00 -66.00 104.97  176
 41  ω     53.00  84.00   0.50    0.41    --   74.00  75.00-141.43   62
 42  ω    105.00 131.00   0.50    0.41    --   74.00  75.00-141.43   52
 43  ω     52.00  77.00   0.50    0.41    --   74.00  77.00 175.49   50
 44  ω    -87.00 -61.00   0.50    1.64    --  -78.00 -64.00 -37.44   52
 45  ω    -94.00 -58.00   0.50    1.64    --  -78.00 -73.00  34.95   72
 46  ω    -90.00 -64.00   0.50    1.64    --  -86.25 -77.00 150.00   52
 47  ω    -91.00 -65.00   0.50    1.64    --  -86.25 -77.00  90.00   52
 48  ω   -102.00 -66.00   0.50    1.64    --  -86.25 -72.00 121.89   72
 49  ω    -98.00 -70.00   0.50    1.64    --  -86.25 -63.00 -96.10   56
 50  ω    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00-150.00   50
 51  ω   -109.00 -69.00   0.50    1.64    --  -86.25 -71.00 165.50   80
 52  ω    -92.00 -65.00   0.50    1.64    --  -86.25 -75.00  47.49   54
 53  ω    -99.00 -66.00   0.50    1.64    --  -86.25 -77.00  30.00   66
 54  ω   -101.00 -64.00   0.50    1.64    --  -86.25 -77.00 -30.00   74
 55  ω   -141.00-115.00   0.50    1.64    --  -86.25 -77.00 -90.00   52
 56  ω    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00 -90.00   50
 57  ω    -89.00 -64.00   0.50    1.64    --  -86.25 -77.00-180.00   50
 58  ω    -93.00 -67.00   0.50    1.64    --  -86.25 -72.00-108.85   52
 59  ω    -95.00 -66.00   0.50    1.64    --  -86.25 -77.00-120.00   58
 60  ω   -112.00 -67.00   0.50    1.64    --  -86.25 -75.00  11.02   90
 61  ω   -101.00 -69.00   0.50    1.64    --  -86.25 -71.00-177.00   64
 62  ω    -95.00 -69.00   0.50    1.64    --  -86.25 -70.00  67.22   52
 63  ω    -93.00 -66.00   0.50    1.64    --  -86.25 -74.00-134.94   54
 64  ω   -115.00 -68.00   0.50    1.64    --  -86.25 -72.00 105.60   94
 65  ω    -84.00 -59.00   0.50    1.64    --  -86.25 125.00   0.00   50
 66  ω    -93.00 -67.00   0.50    1.64    --  -86.25 -76.00 -45.58   52
 67  ω    123.00 177.00   0.50    1.64    --  107.75  30.00  60.00  108
 68  ω     83.00 111.00   0.50    1.64    --  107.75-125.00 -90.00   56
 69  ω     39.00  98.00   0.50    1.64    --  107.75 -95.00 120.00  118
 70  ω     42.00  68.00   0.50    1.64    --  107.75 -77.00 -30.00   52
 71  ω     43.00  68.00   0.50    1.64    --  107.75-125.00 -90.00   50
 72  ω    124.00 177.00   0.50    1.64    --  107.75  45.00 -90.00  106
 73  ω     88.00 173.00   0.50    1.64    --  107.75  77.00 150.00  170
 74  ω     72.00 111.00   0.50    1.64    --  107.75-125.00-150.00   78
 75  ω     37.00  87.00   0.50    1.64    --  107.75 -77.00 -60.00  100
 76  ω    129.00 155.00   0.50    1.64    --  107.75  61.00 150.00   52
 77  ω     95.00 121.00   0.50    1.64    --  107.75  61.00 150.00   52
 78  ω     95.00 125.00   0.50    1.64    --  107.75  61.00 -60.00   60
 79  ω    124.00 178.00   0.50    1.64    --  107.75  77.00 -30.00  108
 80  ω    123.00 159.00   0.50    1.64    --  107.75  30.00-150.00   72
 81  ω     89.00 116.00   0.50    1.64    --  107.75  77.00 -30.00   54
 82  ω    145.00 176.00   0.50    1.64    --  107.75  77.00-120.00   62
 83  ω     79.00 105.00   0.50    1.64    --  107.75 -95.00-120.00   52
 84  ω     88.00 128.00   0.50    1.64    --  107.75  77.00-120.00   80
 85  ω     80.00 109.00   0.50    1.64    --  107.75-125.00 -60.00   58
 86  ω     41.00  95.00   0.50    1.64    --  107.75 -77.00  90.00  108
 87  ω     70.00  96.00   0.50    1.64    --  107.75 -77.00-180.00   52
 88  ω     88.00 176.00   0.50    1.64    --  107.75  77.00 120.00  176
 89  ω     37.00  63.00   0.50    1.64    --  107.75 -61.00   0.00   52
 90  ω     92.00 124.00   0.50    1.64    --  107.75  77.00 -60.00   64
 91  ω     69.00  96.00   0.50    1.64    --  107.75 -95.00 -90.00   54
 92  ω    147.00 174.00   0.50    1.64    --  107.75  77.00   0.00   54
 93  ω     40.00  66.00   0.50    1.64    --  107.75-125.00 -60.00   52
 94  ω     36.00  71.00   0.50    1.64    --  107.75 -95.00 -60.00   70
 95  ω     38.00  64.00   0.50    1.64    --  107.75 -95.00 -90.00   52
 96  ω     94.00 140.00   0.50    1.64    --  107.75  61.00  60.00   92
 97  ω     94.00 124.00   0.50    1.64    --  107.75  61.00 -90.00   60
 98  ω     86.00 127.00   0.50    1.64    --  107.75  77.00   0.00   82
 99  ω    148.00 174.00   0.50    1.64    --  107.75  61.00-120.00   52
100  ω     93.00 127.00   0.50    1.64    --  107.75  61.00-120.00   68
101  ω     74.00 111.00   0.50    1.64    --  107.75-125.00 120.00   74
102  ω     36.00  63.00   0.50    1.64    --  107.75 -77.00-180.00   54
103  ω     40.00  65.00   0.50    1.64    --  107.75-125.00 120.00   50
104  ω     41.00  66.00   0.50    1.64    --  107.75 -77.00  30.00   50
105  ω    133.00 177.00   0.50    1.64    --  107.75  77.00-150.00   88
106  ω     43.00  69.00   0.50    1.64    --  107.75 -95.00-120.00   52
107  ω    138.00 163.00   0.50    1.64    --  107.75  45.00  90.00   50
108  ω     80.00 105.00   0.50    1.64    --  107.75 -95.00  90.00   50
109  ω     81.00 110.00   0.50    1.64    --  107.75-125.00   0.00   58
110  ω    133.00 176.00   0.50    1.64    --  107.75  45.00 -60.00   86
111  ω     39.00  69.00   0.50    1.64    --  107.75-125.00   0.00   60
112  ω    142.00 170.00   0.50    1.64    --  107.75  30.00  30.00   56
113  ω    104.00 130.00   0.50    1.64    --  107.75 125.00 120.00   52
114  ω    147.00 176.00   0.50    1.64    --  107.75 125.00 120.00   58
115  ω     88.00 129.00   0.50    1.64    --  107.75  77.00-150.00   82
116  ω     94.00 168.00   0.50    1.64    --  107.75  61.00  90.00  148
117  ω     96.00 125.00   0.50    1.64    --  107.75  61.00   0.00   58
118  ω    124.00 165.00   0.50    1.64    --  107.75  45.00 -30.00   82
119  ω     99.00 129.00   0.50    1.64    --  107.75  45.00  90.00   60
120  ω     40.00 105.00   0.50    1.64    --  107.75-125.00-180.00  130
121  ω     94.00 126.00   0.50    1.64    --  107.75  61.00 -30.00   64
122  ω     95.00 154.00   0.50    1.64    --  107.75  61.00-180.00  118
123  ω    137.00 163.00   0.50    1.64    --  107.75  77.00 -90.00   52
124  ω     40.00  66.00   0.50    1.64    --  107.75 -77.00 120.00   52
125  ω     86.00 156.00   0.50    1.64    --  107.75  77.00-180.00  140
126  ω    125.00 165.00   0.50    1.64    --  107.75 125.00-180.00   80
127  ω     45.00  70.00   0.50    1.64    --  107.75 -61.00-120.00   50
128  ω     37.00  64.00   0.50    1.64    --  107.75 -77.00-150.00   54
129  ω     86.00 126.00   0.50    1.64    --  107.75  77.00 -90.00   80
130  ω     47.00  95.00   0.50    1.64    --  107.75 -98.00  -1.50   96
131  ω     86.00 145.00   0.50    1.64    --  107.75  77.00  90.00  118
132  ω    138.00 172.00   0.50    1.64    --  107.75  77.00  30.00   68
133  ω     97.00 173.00   0.50    1.64    --  107.75  45.00   0.00  152
134  ω     72.00  98.00   0.50    1.64    --  107.75 -77.00 150.00   52
135  ω     42.00  68.00   0.50    1.64    --  107.75 -77.00 150.00   52
136  ω    136.00 162.00   0.50    1.64    --  107.75  77.00  60.00   52
137  ω     89.00 131.00   0.50    1.64    --  107.75  77.00  30.00   84
138  ω     96.00 160.00   0.50    1.64    --  107.75  61.00 120.00  128
139  ω     86.00 111.00   0.50    1.64    --  107.75  77.00  60.00   50
140  ω     97.00 155.00   0.50    1.64    --  107.75  61.00-150.00  116
141  ω     39.00 111.00   0.50    1.64    --  107.75-125.00  90.00  144
142  ω     43.00 106.00   0.50    1.64    --  107.75-108.00  37.72  126
143  ω     36.00  70.00   0.50    1.64    --  107.75 -61.00 150.00   68
144  ω     74.00 105.00   0.50    1.64    --  107.75 -95.00 -60.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0294230000
_diffrn_orient_matrix_UB_12      -0.1462218000
_diffrn_orient_matrix_UB_13      0.0392173000
_diffrn_orient_matrix_UB_21      0.1608722000
_diffrn_orient_matrix_UB_22      -0.0491269000
_diffrn_orient_matrix_UB_23      0.0545402000
_diffrn_orient_matrix_UB_31      -0.1062724000
_diffrn_orient_matrix_UB_32      0.0052265000
_diffrn_orient_matrix_UB_33      0.1207401000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3886
_reflns_number_total             4157
_reflns_odcompleteness_completeness 97.49
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.52
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         4157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0354
_refine_ls_restrained_S_all      1.035
_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)+(0.0463P)²+0.3690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0935
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C17(H17), C22(H22)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
O5 O 0.28341(10) 0.45784(8) 0.38002(8) 0.02810(19) Uani 1 1 d . . . . .
O14 O 0.75947(10) 0.57671(8) 0.16011(7) 0.02325(18) Uani 1 1 d . . . . .
O16 O 1.03139(11) 0.69113(8) -0.00045(7) 0.0297(2) Uani 1 1 d . . . . .
O19 O 1.11145(10) 0.31603(8) 0.24708(7) 0.02322(18) Uani 1 1 d . . . . .
N1 N 0.20621(12) 0.88795(10) 0.11857(9) 0.0243(2) Uani 1 1 d . . . . .
H1 H 0.242(2) 0.9718(18) 0.0764(16) 0.046(5) Uiso 1 1 d . . . . .
N3 N 0.47220(12) 0.73443(9) 0.15362(9) 0.0242(2) Uani 1 1 d . . . . .
N4 N 0.47900(12) 0.60058(9) 0.23888(8) 0.0229(2) Uani 1 1 d . . . . .
N6 N 0.21404(12) 0.67814(9) 0.25107(8) 0.0214(2) Uani 1 1 d . . . . .
C2 C 0.30953(14) 0.77359(11) 0.16695(10) 0.0219(2) Uani 1 1 d . . . . .
C5 C 0.32120(14) 0.56324(11) 0.30138(10) 0.0223(2) Uani 1 1 d . . . . .
C7 C 0.04178(14) 0.73313(11) 0.26254(10) 0.0220(2) Uani 1 1 d . . . . .
C8 C -0.10221(15) 0.68210(12) 0.33681(11) 0.0260(2) Uani 1 1 d . . . . .
H8 H -0.098318 0.593479 0.394701 0.031 Uiso 1 1 calc R U . . .
C9 C -0.25410(16) 0.76773(13) 0.32233(12) 0.0297(3) Uani 1 1 d . . . . .
H9 H -0.357105 0.736728 0.371128 0.036 Uiso 1 1 calc R U . . .
C10 C -0.25813(16) 0.89813(13) 0.23764(11) 0.0294(3) Uani 1 1 d . . . . .
H10 H -0.364312 0.953049 0.229284 0.035 Uiso 1 1 calc R U . . .
C11 C -0.11137(16) 0.95015(12) 0.16508(11) 0.0267(2) Uani 1 1 d . . . . .
H11 H -0.114822 1.039739 0.109062 0.032 Uiso 1 1 calc R U . . .
C12 C 0.04020(15) 0.86510(11) 0.17835(10) 0.0227(2) Uani 1 1 d . . . . .
C13 C 0.63524(14) 0.51847(11) 0.25276(10) 0.0214(2) Uani 1 1 d . . . . .
C15 C 0.92038(14) 0.50734(11) 0.16501(10) 0.0214(2) Uani 1 1 d . . . . .
C16 C 1.05535(15) 0.57611(11) 0.07452(10) 0.0240(2) Uani 1 1 d . . . . .
C17 C 1.21959(15) 0.49679(12) 0.08084(10) 0.0268(2) Uani 1 1 d . . . . .
H17 H 1.315126 0.533264 0.024335 0.032 Uiso 1 1 calc R U . . .
C18 C 1.24283(15) 0.37285(12) 0.16384(10) 0.0257(2) Uani 1 1 d . . . . .
C20 C 0.95170(14) 0.38381(11) 0.24757(10) 0.0207(2) Uani 1 1 d . . . . .
C21 C 0.82159(13) 0.30723(10) 0.34594(9) 0.0200(2) Uani 1 1 d . . . . .
C22 C 0.65643(14) 0.40108(11) 0.34130(10) 0.0239(2) Uani 1 1 d . . . . .
H22 H 0.562932 0.374701 0.405055 0.029 Uiso 1 1 calc R U . . .
C23 C 0.80621(15) 0.18126(11) 0.32420(10) 0.0232(2) Uani 1 1 d . . . . .
H23A H 0.767778 0.209699 0.247512 0.028 Uiso 1 1 calc R U . . .
H23B H 0.918934 0.126728 0.317448 0.028 Uiso 1 1 calc R U . . .
C24 C 0.68154(15) 0.09569(12) 0.42581(10) 0.0261(2) Uani 1 1 d . . . . .
H24A H 0.566918 0.147894 0.429032 0.031 Uiso 1 1 calc R U . . .
H24B H 0.676904 0.015556 0.409844 0.031 Uiso 1 1 calc R U . . .
C25 C 0.73478(15) 0.05187(11) 0.54628(10) 0.0248(2) Uani 1 1 d . . . . .
H25A H 0.843088 -0.009269 0.546210 0.030 Uiso 1 1 calc R U . . .
H25B H 0.648191 0.002026 0.611059 0.030 Uiso 1 1 calc R U . . .
C26 C 0.75599(14) 0.17166(11) 0.57137(10) 0.0228(2) Uani 1 1 d . . . . .
H26A H 0.801585 0.138736 0.645829 0.027 Uiso 1 1 calc R U . . .
H26B H 0.643688 0.224792 0.584541 0.027 Uiso 1 1 calc R U . . .
C27 C 0.87459(14) 0.26218(11) 0.46864(9) 0.0212(2) Uani 1 1 d . . . . .
H27A H 0.991205 0.213489 0.464039 0.025 Uiso 1 1 calc R U . . .
H27B H 0.875020 0.342416 0.485829 0.025 Uiso 1 1 calc R U . . .
C28 C 1.40530(15) 0.28207(13) 0.17901(12) 0.0318(3) Uani 1 1 d . . . . .
H28A H 1.429603 0.265200 0.257290 0.048 Uiso 1 1 calc R U . . .
H28B H 1.496837 0.324048 0.115360 0.048 Uiso 1 1 calc R U . . .
H28C H 1.396605 0.197086 0.174394 0.048 Uiso 1 1 calc R U . . .
O20 O 0.73251(12) 0.85868(8) -0.03465(8) 0.0303(2) Uani 1 1 d . . . . .
H20A H 0.832(3) 0.801(2) -0.0198(18) 0.064(6) Uiso 1 1 d . . . . .
H20B H 0.656(3) 0.8208(19) 0.0279(18) 0.055(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
O5 C5 1.2203(14) . ?
O14 C13 1.3681(13) . ?
O14 C15 1.3780(13) . ?
O16 C16 1.2420(14) . ?
O19 C18 1.3549(13) . ?
O19 C20 1.3606(13) . ?
N1 H1 0.933(18) . ?
N1 C2 1.3590(14) . ?
N1 C12 1.4026(15) . ?
N3 N4 1.4256(12) . ?
N3 C2 1.3030(15) . ?
N4 C5 1.3880(14) . ?
N4 C13 1.4053(14) . ?
N6 C2 1.3702(14) . ?
N6 C5 1.3856(14) . ?
N6 C7 1.4086(14) . ?
C7 C8 1.3753(16) . ?
C7 C12 1.4067(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3932(17) . ?
C9 H9 0.9500 . ?
C9 C10 1.3959(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3914(18) . ?
C11 H11 0.9500 . ?
C11 C12 1.3870(16) . ?
C13 C22 1.3279(15) . ?
C15 C16 1.4557(15) . ?
C15 C20 1.3505(15) . ?
C16 C17 1.4397(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3465(17) . ?
C18 C28 1.4861(17) . ?
C20 C21 1.5000(15) . ?
C21 C22 1.5118(15) . ?
C21 C23 1.5537(14) . ?
C21 C27 1.5505(14) . ?
C22 H22 0.9500 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5298(15) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5277(16) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5276(15) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5307(15) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O20 H20A 0.93(2) . ?
O20 H20B 0.88(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
C13 O14 C15 115.26(8) . . ?
C18 O19 C20 120.11(9) . . ?
C2 N1 H1 124.0(11) . . ?
C2 N1 C12 106.84(9) . . ?
C12 N1 H1 125.6(11) . . ?
C2 N3 N4 101.36(9) . . ?
C5 N4 N3 113.79(9) . . ?
C5 N4 C13 125.69(9) . . ?
C13 N4 N3 120.51(9) . . ?
C2 N6 C5 108.90(9) . . ?
C2 N6 C7 109.41(9) . . ?
C5 N6 C7 141.49(10) . . ?
N1 C2 N6 109.59(10) . . ?
N3 C2 N1 136.18(11) . . ?
N3 C2 N6 114.22(10) . . ?
O5 C5 N4 130.16(10) . . ?
O5 C5 N6 128.13(11) . . ?
N6 C5 N4 101.71(9) . . ?
C8 C7 N6 132.39(10) . . ?
C8 C7 C12 123.08(11) . . ?
C12 C7 N6 104.51(9) . . ?
C7 C8 H8 121.9 . . ?
C7 C8 C9 116.21(11) . . ?
C9 C8 H8 121.9 . . ?
C8 C9 H9 119.3 . . ?
C8 C9 C10 121.39(11) . . ?
C10 C9 H9 119.3 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 122.01(11) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 H11 121.6 . . ?
C12 C11 C10 116.90(11) . . ?
C12 C11 H11 121.6 . . ?
N1 C12 C7 109.58(10) . . ?
C11 C12 N1 130.05(10) . . ?
C11 C12 C7 120.38(11) . . ?
O14 C13 N4 109.57(9) . . ?
C22 C13 O14 125.80(10) . . ?
C22 C13 N4 124.61(10) . . ?
O14 C15 C16 115.42(9) . . ?
C20 C15 O14 122.62(10) . . ?
C20 C15 C16 121.96(10) . . ?
O16 C16 C15 123.55(11) . . ?
O16 C16 C17 123.49(11) . . ?
C17 C16 C15 112.97(10) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 C16 122.46(11) . . ?
C18 C17 H17 118.8 . . ?
O19 C18 C28 111.39(10) . . ?
C17 C18 O19 121.37(11) . . ?
C17 C18 C28 127.24(11) . . ?
O19 C20 C21 113.30(9) . . ?
C15 C20 O19 121.10(10) . . ?
C15 C20 C21 125.59(10) . . ?
C20 C21 C22 106.40(9) . . ?
C20 C21 C23 109.73(9) . . ?
C20 C21 C27 109.90(9) . . ?
C22 C21 C23 110.50(9) . . ?
C22 C21 C27 111.30(9) . . ?
C27 C21 C23 108.99(8) . . ?
C13 C22 C21 123.42(10) . . ?
C13 C22 H22 118.3 . . ?
C21 C22 H22 118.3 . . ?
C21 C23 H23A 109.3 . . ?
C21 C23 H23B 109.3 . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 C21 111.73(9) . . ?
C24 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 C23 110.88(9) . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C24 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C24 C25 C26 111.64(9) . . ?
H25A C25 H25B 108.0 . . ?
C26 C25 H25A 109.3 . . ?
C26 C25 H25B 109.3 . . ?
C25 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C25 C26 C27 112.46(9) . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C21 C27 H27A 109.1 . . ?
C21 C27 H27B 109.1 . . ?
C26 C27 C21 112.42(9) . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.9 . . ?
C18 C28 H28A 109.5 . . ?
C18 C28 H28B 109.5 . . ?
C18 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
H20A O20 H20B 103.5(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
N1 H1 O20 0.933(18) 1.771(18) 2.6741(13) 162.0(16) 2_675 yes
C22 H22 O5 0.95 2.34 2.9520(14) 122.0 . yes
C28 H28C O20 0.98 2.58 3.3228(16) 132.4 2_765 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
O14 C13 C22 C21 -6.06(18) . . . . ?
O14 C15 C16 O16 2.32(16) . . . . ?
O14 C15 C16 C17 -177.58(9) . . . . ?
O14 C15 C20 O19 177.50(9) . . . . ?
O14 C15 C20 C21 -2.06(17) . . . . ?
O16 C16 C17 C18 179.19(11) . . . . ?
O19 C20 C21 C22 174.50(8) . . . . ?
O19 C20 C21 C23 -65.94(11) . . . . ?
O19 C20 C21 C27 53.89(12) . . . . ?
N3 N4 C5 O5 -179.25(11) . . . . ?
N3 N4 C5 N6 0.84(12) . . . . ?
N3 N4 C13 O14 -12.23(14) . . . . ?
N3 N4 C13 C22 169.16(11) . . . . ?
N4 N3 C2 N1 179.12(13) . . . . ?
N4 N3 C2 N6 -0.30(12) . . . . ?
N4 C13 C22 C21 172.32(10) . . . . ?
N6 C7 C8 C9 179.90(11) . . . . ?
N6 C7 C12 N1 0.05(12) . . . . ?
N6 C7 C12 C11 -179.92(10) . . . . ?
C2 N1 C12 C7 -1.62(12) . . . . ?
C2 N1 C12 C11 178.35(11) . . . . ?
C2 N3 N4 C5 -0.36(12) . . . . ?
C2 N3 N4 C13 178.78(9) . . . . ?
C2 N6 C5 O5 179.12(11) . . . . ?
C2 N6 C5 N4 -0.97(11) . . . . ?
C2 N6 C7 C8 -176.81(12) . . . . ?
C2 N6 C7 C12 1.54(12) . . . . ?
C5 N4 C13 O14 166.81(10) . . . . ?
C5 N4 C13 C22 -11.80(18) . . . . ?
C5 N6 C2 N1 -178.71(9) . . . . ?
C5 N6 C2 N3 0.86(13) . . . . ?
C5 N6 C7 C8 -2.8(2) . . . . ?
C5 N6 C7 C12 175.57(13) . . . . ?
C7 N6 C2 N1 -2.64(12) . . . . ?
C7 N6 C2 N3 176.94(9) . . . . ?
C7 N6 C5 O5 5.1(2) . . . . ?
C7 N6 C5 N4 -175.01(13) . . . . ?
C7 C8 C9 C10 -0.54(17) . . . . ?
C8 C7 C12 N1 178.60(10) . . . . ?
C8 C7 C12 C11 -1.37(17) . . . . ?
C8 C9 C10 C11 -1.19(19) . . . . ?
C9 C10 C11 C12 1.63(17) . . . . ?
C10 C11 C12 N1 179.64(11) . . . . ?
C10 C11 C12 C7 -0.40(16) . . . . ?
C12 N1 C2 N3 -176.85(13) . . . . ?
C12 N1 C2 N6 2.59(12) . . . . ?
C12 C7 C8 C9 1.80(17) . . . . ?
C13 O14 C15 C16 -173.21(9) . . . . ?
C13 O14 C15 C20 7.00(15) . . . . ?
C13 N4 C5 O5 1.66(19) . . . . ?
C13 N4 C5 N6 -178.26(10) . . . . ?
C15 O14 C13 N4 178.37(8) . . . . ?
C15 O14 C13 C22 -3.04(16) . . . . ?
C15 C16 C17 C18 -0.91(16) . . . . ?
C15 C20 C21 C22 -5.91(15) . . . . ?
C15 C20 C21 C23 113.65(12) . . . . ?
C15 C20 C21 C27 -126.52(11) . . . . ?
C16 C15 C20 O19 -2.27(16) . . . . ?
C16 C15 C20 C21 178.16(10) . . . . ?
C16 C17 C18 O19 -0.38(18) . . . . ?
C16 C17 C18 C28 179.97(11) . . . . ?
C18 O19 C20 C15 0.85(15) . . . . ?
C18 O19 C20 C21 -179.54(9) . . . . ?
C20 O19 C18 C17 0.49(16) . . . . ?
C20 O19 C18 C28 -179.81(9) . . . . ?
C20 C15 C16 O16 -177.88(11) . . . . ?
C20 C15 C16 C17 2.21(15) . . . . ?
C20 C21 C22 C13 9.70(15) . . . . ?
C20 C21 C23 C24 177.01(9) . . . . ?
C20 C21 C27 C26 -174.33(9) . . . . ?
C21 C23 C24 C25 -57.90(13) . . . . ?
C22 C21 C23 C24 -65.97(11) . . . . ?
C22 C21 C27 C26 68.06(11) . . . . ?
C23 C21 C22 C13 -109.36(12) . . . . ?
C23 C21 C27 C26 -54.05(12) . . . . ?
C23 C24 C25 C26 55.15(13) . . . . ?
C24 C25 C26 C27 -53.09(13) . . . . ?
C25 C26 C27 C21 53.30(12) . . . . ?
C27 C21 C22 C13 129.41(11) . . . . ?
C27 C21 C23 C24 56.62(12) . . . . ?

_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 1.214
_oxdiff_exptl_absorpt_empirical_full_min 0.825
####################################################################### 
# 
# 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_tet-acid-2
_database_code_depnum_ccdc_archive 'CCDC 2270314'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N2O2
_chemical_oxdiff_usercomment     TET-Acid-2
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.69260(10)
_cell_length_b                   11.74390(10)
_cell_length_c                   13.59140(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.3170(10)
_cell_angle_gamma                90
_cell_volume                     1851.13(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14884
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      77.3330
_cell_measurement_theta_min      3.7740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.814
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (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_density_diffrn    1.372
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.762
_diffrn_reflns_theta_min         3.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(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 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 -39.00   0.50    0.40    --  -48.70 116.00 -18.00   50
  2  ω   -106.00 -79.00   0.50    0.40    --  -48.70-167.00 107.00   54
  3  ω     44.00  76.00   0.50    0.40    --   48.70-116.00-106.00   64
  4  ω     72.00 121.00   0.50    0.40    --   48.70-167.00 107.00   98
  5  ω   -141.00-115.00   0.50    2.00    --  -86.25-116.00-106.00   52
  6  ω    -86.00 -61.00   0.50    2.00    --  -86.25 167.00 128.00   50
  7  ω     74.00  99.00   0.50    2.00    --  107.75-167.00 107.00   50
  8  ω    101.00 148.00   0.50    2.00    --  107.75 167.00 128.00   94
  9  ω    119.00 146.00   0.50    2.00    --  107.75 116.00 -18.00   54
 10  ω     74.00 109.00   0.50    2.00    --  107.75-116.00-106.00   70
 11  ω    -24.00  25.00   0.50    0.40    --  -48.70  19.00  60.00   98
 12  ω   -119.00 -28.00   0.50    0.40    --  -48.70 -77.00 -90.00  182
 13  ω   -117.00 -79.00   0.50    0.40    --  -48.70-125.00  60.00   76
 14  ω   -117.00 -75.00   0.50    0.40    --  -48.70-125.00 -60.00   84
 15  ω     38.00  79.00   0.50    2.00    --  107.75-100.00 -49.59   82
 16  ω     36.00  61.00   0.50    2.00    --  107.75 -61.00 150.00   50
 17  ω     97.00 175.00   0.50    2.00    --  107.75  15.00  90.00  156
 18  ω    142.00 176.00   0.50    2.00    --  107.75  52.00-111.36   68
 19  ω     45.00  73.00   0.50    2.00    --  107.75-125.00   0.00   56
 20  ω     52.00 105.00   0.50    2.00    --  107.75 -95.00-120.00  106
 21  ω     36.00  70.00   0.50    2.00    --  107.75 -61.00 -30.00   68
 22  ω     79.00 110.00   0.50    2.00    --  107.75-125.00  30.00   62
 23  ω    113.00 139.00   0.50    2.00    --  107.75  30.00 -60.00   52
 24  ω    151.00 178.00   0.50    2.00    --  107.75  30.00 -60.00   54
 25  ω     51.00 102.00   0.50    2.00    --  107.75 -77.00   0.00  102
 26  ω    133.00 168.00   0.50    2.00    --  107.75 125.00-180.00   70
 27  ω     38.00  63.00   0.50    2.00    --  107.75 -77.00  90.00   50
 28  ω    104.00 129.00   0.50    2.00    --  107.75  52.00-111.36   50
 29  ω     79.00 104.00   0.50    2.00    --  107.75 -77.00 120.00   50
 30  ω     65.00 108.00   0.50    2.00    --  107.75-111.00 -20.51   86
 31  ω    106.00 163.00   0.50    2.00    --  107.75  98.00  12.93  114
 32  ω    105.00 152.00   0.50    2.00    --  107.75  15.00-150.00   94
 33  ω     97.00 164.00   0.50    2.00    --  107.75  77.00   0.00  134
 34  ω     40.00 102.00   0.50    2.00    --  107.75 -95.00 120.00  124
 35  ω     97.00 126.00   0.50    2.00    --  107.75  45.00-180.00   58
 36  ω    105.00 151.00   0.50    2.00    --  107.75  30.00 -30.00   92
 37  ω     43.00  71.00   0.50    2.00    --  107.75 -61.00 -60.00   56
 38  ω     79.00 105.00   0.50    2.00    --  107.75 -97.00-121.25   52
 39  ω     47.00  88.00   0.50    2.00    --  107.75 -77.00-180.00   82
 40  ω     50.00  75.00   0.50    2.00    --  107.75 -77.00 120.00   50
 41  ω     36.00  62.00   0.50    2.00    --  107.75 -77.00-120.00   52
 42  ω     44.00  96.00   0.50    2.00    --  107.75 -95.00 150.00  104
 43  ω     82.00 108.00   0.50    2.00    --  107.75-115.00  35.28   52
 44  ω     60.00 106.00   0.50    2.00    --  107.75 -92.00 -96.34   92
 45  ω     76.00 111.00   0.50    2.00    --  107.75-125.00 -30.00   70
 46  ω     74.00 111.00   0.50    2.00    --  107.75 -85.00 -68.22   74
 47  ω     36.00  62.00   0.50    2.00    --  107.75 -61.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0356478000
_diffrn_orient_matrix_UB_12      0.0600752000
_diffrn_orient_matrix_UB_13      0.0921076000
_diffrn_orient_matrix_UB_21      -0.0404301000
_diffrn_orient_matrix_UB_22      -0.1147645000
_diffrn_orient_matrix_UB_23      0.0382806000
_diffrn_orient_matrix_UB_31      0.1214894000
_diffrn_orient_matrix_UB_32      -0.0206331000
_diffrn_orient_matrix_UB_33      0.0556518000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3707
_reflns_number_total             3929
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.031
_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)+(0.0536P)²+0.7635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1050
_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 C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2B,H2C), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.92673(7) 0.63820(7) 0.45553(6) 0.0231(2) Uani 1 1 d . . . . .
O2 O 0.52956(7) 0.33714(7) 0.38355(6) 0.01959(19) Uani 1 1 d . . . . .
O3 O 0.35902(7) 0.25296(7) 0.34090(6) 0.0238(2) Uani 1 1 d . . . . .
O4 O 0.57648(7) 0.51950(7) 0.18341(6) 0.02198(19) Uani 1 1 d . . . . .
H4 H 0.6483(18) 0.5519(17) 0.2144(16) 0.049(5) Uiso 1 1 d . . . . .
O5 O 0.27322(8) 0.30873(8) 0.13581(7) 0.0292(2) Uani 1 1 d . . . . .
N1 N 0.76940(8) 0.53906(8) 0.38130(7) 0.0177(2) Uani 1 1 d . . . . .
N2 N 0.76892(8) 0.58960(9) 0.28730(7) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.7584(15) 0.6640(16) 0.2937(13) 0.033(4) Uiso 1 1 d . . . . .
C1 C 0.85000(10) 0.57088(10) 0.46175(8) 0.0192(2) Uani 1 1 d . . . . .
C2 C 0.81986(10) 0.50646(11) 0.54993(9) 0.0226(3) Uani 1 1 d . . . . .
H2B H 0.788674 0.558692 0.597120 0.027 Uiso 1 1 calc R U . . .
H2C H 0.888967 0.468126 0.584548 0.027 Uiso 1 1 calc R U . . .
C3 C 0.72803(9) 0.41772(10) 0.50992(8) 0.0186(2) Uani 1 1 d . . . . .
C4 C 0.68869(9) 0.46022(9) 0.40443(8) 0.0168(2) Uani 1 1 d . . . . .
C5 C 0.78323(10) 0.29911(10) 0.50042(9) 0.0223(2) Uani 1 1 d . . . . .
H5A H 0.725683 0.247584 0.463910 0.027 Uiso 1 1 calc R U . . .
H5B H 0.848818 0.306271 0.461403 0.027 Uiso 1 1 calc R U . . .
C6 C 0.82601(12) 0.24674(12) 0.60141(10) 0.0290(3) Uani 1 1 d . . . . .
H6A H 0.853171 0.168131 0.591951 0.035 Uiso 1 1 calc R U . . .
H6B H 0.892000 0.291609 0.633778 0.035 Uiso 1 1 calc R U . . .
C7 C 0.73051(12) 0.24449(12) 0.66834(10) 0.0306(3) Uani 1 1 d . . . . .
H7A H 0.668618 0.192178 0.639786 0.037 Uiso 1 1 calc R U . . .
H7B H 0.762073 0.215007 0.734494 0.037 Uiso 1 1 calc R U . . .
C8 C 0.67982(11) 0.36266(12) 0.67977(9) 0.0252(3) Uani 1 1 d . . . . .
H8A H 0.740211 0.413939 0.712604 0.030 Uiso 1 1 calc R U . . .
H8B H 0.617016 0.357998 0.722050 0.030 Uiso 1 1 calc R U . . .
C9 C 0.63248(10) 0.41123(10) 0.57788(8) 0.0204(2) Uani 1 1 d . . . . .
H9A H 0.600827 0.488318 0.586222 0.025 Uiso 1 1 calc R U . . .
H9B H 0.569068 0.362204 0.546773 0.025 Uiso 1 1 calc R U . . .
C10 C 0.59592(9) 0.42085(9) 0.34419(8) 0.0176(2) Uani 1 1 d . . . . .
C11 C 0.43233(10) 0.31550(10) 0.31652(8) 0.0192(2) Uani 1 1 d . . . . .
C12 C 0.44109(10) 0.38078(10) 0.22723(8) 0.0189(2) Uani 1 1 d . . . . .
C13 C 0.54011(9) 0.44597(10) 0.24487(8) 0.0177(2) Uani 1 1 d . . . . .
C14 C 0.35404(10) 0.37572(10) 0.13950(9) 0.0211(2) Uani 1 1 d . . . . .
C15 C 0.36538(11) 0.45329(12) 0.05371(10) 0.0297(3) Uani 1 1 d . . . . .
H15A H 0.431044 0.429125 0.020607 0.045 Uiso 1 1 calc R U . . .
H15B H 0.377835 0.531502 0.077843 0.045 Uiso 1 1 calc R U . . .
H15C H 0.294677 0.449945 0.006578 0.045 Uiso 1 1 calc R U . . .
C16 C 0.86899(9) 0.56501(10) 0.23836(8) 0.0186(2) Uani 1 1 d . . . . .
C17 C 0.93873(10) 0.47087(10) 0.26162(9) 0.0209(2) Uani 1 1 d . . . . .
H17 H 0.924501 0.421263 0.313921 0.025 Uiso 1 1 calc R U . . .
C18 C 1.03010(11) 0.44978(11) 0.20732(9) 0.0251(3) Uani 1 1 d . . . . .
H18 H 1.078337 0.385504 0.222945 0.030 Uiso 1 1 calc R U . . .
C19 C 1.05102(11) 0.52154(13) 0.13104(9) 0.0280(3) Uani 1 1 d . . . . .
H19 H 1.113517 0.506746 0.094547 0.034 Uiso 1 1 calc R U . . .
C20 C 0.98032(11) 0.61547(12) 0.10786(9) 0.0278(3) Uani 1 1 d . . . . .
H20 H 0.994351 0.664656 0.055211 0.033 Uiso 1 1 calc R U . . .
C21 C 0.88930(10) 0.63763(11) 0.16139(9) 0.0233(3) Uani 1 1 d . . . . .
H21 H 0.841133 0.701927 0.145636 0.028 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 C1 1.2069(15) . ?
O2 C10 1.4001(14) . ?
O2 C11 1.3869(13) . ?
O3 C11 1.2067(15) . ?
O4 H4 0.97(2) . ?
O4 C13 1.3095(14) . ?
O5 C14 1.2257(15) . ?
N1 N2 1.4081(13) . ?
N1 C1 1.4003(14) . ?
N1 C4 1.3865(15) . ?
N2 H2 0.888(19) . ?
N2 C16 1.4467(15) . ?
C1 C2 1.4969(16) . ?
C2 H2B 0.9900 . ?
C2 H2C 0.9900 . ?
C2 C3 1.5447(16) . ?
C3 C4 1.5324(15) . ?
C3 C5 1.5476(16) . ?
C3 C9 1.5396(16) . ?
C4 C10 1.3545(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5289(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5276(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5247(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5343(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C13 1.4528(15) . ?
C11 C12 1.4500(16) . ?
C12 C13 1.3833(16) . ?
C12 C14 1.4670(15) . ?
C14 C15 1.4988(17) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3862(17) . ?
C16 C21 1.3934(17) . ?
C17 H17 0.9500 . ?
C17 C18 1.3957(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.3881(18) . ?
C21 H21 0.9500 . ?

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
C11 O2 C10 109.00(9) . . ?
C13 O4 H4 108.4(12) . . ?
C1 N1 N2 121.37(9) . . ?
C4 N1 N2 124.27(9) . . ?
C4 N1 C1 114.27(9) . . ?
N1 N2 H2 108.1(11) . . ?
N1 N2 C16 115.03(9) . . ?
C16 N2 H2 111.8(11) . . ?
O1 C1 N1 123.54(11) . . ?
O1 C1 C2 129.80(10) . . ?
N1 C1 C2 106.66(9) . . ?
C1 C2 H2B 110.4 . . ?
C1 C2 H2C 110.4 . . ?
C1 C2 C3 106.44(9) . . ?
H2B C2 H2C 108.6 . . ?
C3 C2 H2B 110.4 . . ?
C3 C2 H2C 110.4 . . ?
C2 C3 C5 110.98(9) . . ?
C4 C3 C2 102.83(9) . . ?
C4 C3 C5 107.09(9) . . ?
C4 C3 C9 115.04(9) . . ?
C9 C3 C2 110.32(9) . . ?
C9 C3 C5 110.34(9) . . ?
N1 C4 C3 107.32(9) . . ?
C10 C4 N1 127.36(10) . . ?
C10 C4 C3 125.18(10) . . ?
C3 C5 H5A 109.1 . . ?
C3 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C3 112.30(10) . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 C5 111.17(10) . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.59(11) . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C9 110.28(10) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C8 C9 C3 110.73(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C13 107.00(9) . . ?
C4 C10 O2 116.67(10) . . ?
C4 C10 C13 136.27(11) . . ?
O2 C11 C12 108.27(9) . . ?
O3 C11 O2 118.86(10) . . ?
O3 C11 C12 132.84(10) . . ?
C11 C12 C14 122.90(10) . . ?
C13 C12 C11 107.12(10) . . ?
C13 C12 C14 129.95(11) . . ?
O4 C13 C10 125.65(10) . . ?
O4 C13 C12 125.95(10) . . ?
C12 C13 C10 108.40(10) . . ?
O5 C14 C12 120.72(11) . . ?
O5 C14 C15 120.16(10) . . ?
C12 C14 C15 119.13(10) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 N2 122.76(10) . . ?
C17 C16 C21 120.52(11) . . ?
C21 C16 N2 116.62(10) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.25(11) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.60(12) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.79(12) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.22(12) . . ?
C21 C20 H20 119.9 . . ?
C16 C21 H21 120.2 . . ?
C20 C21 C16 119.61(12) . . ?
C20 C21 H21 120.2 . . ?

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
O4 H4 N1 0.97(2) 2.52(2) 3.2909(12) 136.4(16) . yes
O4 H4 N2 0.97(2) 1.68(2) 2.6317(13) 168.1(19) . yes
N2 H2 O3 0.888(19) 2.384(18) 2.8794(13) 115.5(14) 2_655 yes
N2 H2 O5 0.888(19) 2.009(19) 2.8441(14) 156.2(16) 2_655 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 -170.04(12) . . . . ?
O2 C10 C13 O4 -179.49(10) . . . . ?
O2 C10 C13 C12 1.69(12) . . . . ?
O2 C11 C12 C13 -3.71(13) . . . . ?
O2 C11 C12 C14 178.29(10) . . . . ?
O3 C11 C12 C13 174.22(13) . . . . ?
O3 C11 C12 C14 -3.8(2) . . . . ?
N1 N2 C16 C17 22.07(15) . . . . ?
N1 N2 C16 C21 -161.52(10) . . . . ?
N1 C1 C2 C3 10.09(13) . . . . ?
N1 C4 C10 O2 177.26(10) . . . . ?
N1 C4 C10 C13 -5.7(2) . . . . ?
N2 N1 C1 O1 -3.73(17) . . . . ?
N2 N1 C1 C2 176.15(10) . . . . ?
N2 N1 C4 C3 173.96(9) . . . . ?
N2 N1 C4 C10 -1.96(18) . . . . ?
N2 C16 C17 C18 176.57(10) . . . . ?
N2 C16 C21 C20 -176.65(11) . . . . ?
C1 N1 N2 C16 66.28(13) . . . . ?
C1 N1 C4 C3 -9.64(13) . . . . ?
C1 N1 C4 C10 174.44(11) . . . . ?
C1 C2 C3 C4 -14.98(12) . . . . ?
C1 C2 C3 C5 99.23(11) . . . . ?
C1 C2 C3 C9 -138.15(10) . . . . ?
C2 C3 C4 N1 14.89(12) . . . . ?
C2 C3 C4 C10 -169.08(11) . . . . ?
C2 C3 C5 C6 68.70(13) . . . . ?
C2 C3 C9 C8 -66.86(13) . . . . ?
C3 C4 C10 O2 2.03(17) . . . . ?
C3 C4 C10 C13 179.03(12) . . . . ?
C3 C5 C6 C7 53.32(15) . . . . ?
C4 N1 N2 C16 -117.56(11) . . . . ?
C4 N1 C1 O1 179.75(11) . . . . ?
C4 N1 C1 C2 -0.37(13) . . . . ?
C4 C3 C5 C6 -179.79(10) . . . . ?
C4 C3 C9 C8 177.39(10) . . . . ?
C4 C10 C13 O4 3.3(2) . . . . ?
C4 C10 C13 C12 -175.50(13) . . . . ?
C5 C3 C4 N1 -102.12(10) . . . . ?
C5 C3 C4 C10 73.91(14) . . . . ?
C5 C3 C9 C8 56.12(13) . . . . ?
C5 C6 C7 C8 -55.23(16) . . . . ?
C6 C7 C8 C9 57.84(14) . . . . ?
C7 C8 C9 C3 -58.38(13) . . . . ?
C9 C3 C4 N1 134.85(10) . . . . ?
C9 C3 C4 C10 -49.12(15) . . . . ?
C9 C3 C5 C6 -53.90(13) . . . . ?
C10 O2 C11 O3 -173.44(10) . . . . ?
C10 O2 C11 C12 4.83(12) . . . . ?
C11 O2 C10 C4 173.78(10) . . . . ?
C11 O2 C10 C13 -4.05(12) . . . . ?
C11 C12 C13 O4 -177.62(11) . . . . ?
C11 C12 C13 C10 1.19(13) . . . . ?
C11 C12 C14 O5 -5.28(18) . . . . ?
C11 C12 C14 C15 175.07(11) . . . . ?
C13 C12 C14 O5 177.20(12) . . . . ?
C13 C12 C14 C15 -2.4(2) . . . . ?
C14 C12 C13 O4 0.2(2) . . . . ?
C14 C12 C13 C10 179.01(12) . . . . ?
C16 C17 C18 C19 -0.13(18) . . . . ?
C17 C16 C21 C20 -0.16(17) . . . . ?
C17 C18 C19 C20 -0.19(18) . . . . ?
C18 C19 C20 C21 0.33(19) . . . . ?
C19 C20 C21 C16 -0.16(19) . . . . ?
C21 C16 C17 C18 0.30(17) . . . . ?

_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 2.673
_oxdiff_exptl_absorpt_empirical_full_min 0.415
####################################################################### 
# 
# 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_kjnoim
_database_code_depnum_ccdc_archive 'CCDC 2270307'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2023-03-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N O5, 2(C3 H4 N2)'
_chemical_formula_sum            'C19 H23 N5 O5'
_chemical_formula_weight         401.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C187  H170  N17  O17  '
_chemical_oxdiff_usercomment     KJMOIM
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.5566(2)
_cell_length_b                   9.65170(10)
_cell_length_c                   21.0321(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.9400(10)
_cell_angle_gamma                90
_cell_volume                     3948.59(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20854
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.6830
_cell_measurement_theta_min      4.2270
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -1 -1 0.0172
1 1 1 0.0709
0 1 -1 0.0727
0 -1 1 0.0148
0 -1 -1 0.0152
0 1 1 0.0684
1 0 0 0.0572
-1 0 1 0.0541
0 0 -1 0.0264
-1 1 0 0.0369

_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0015 -1.0001 -0.9982 0.1883 0.0491 0.0217
1.0015 1.0001 0.9982 -0.1883 -0.0491 -0.0217
0.0008 0.9999 -0.9996 -0.1119 -0.0246 0.1330
-0.0008 -0.9999 0.9996 0.1119 0.0246 -0.1330
-0.0014 -1.0002 -0.9988 0.1740 -0.0229 -0.0082
0.0014 1.0002 0.9988 -0.1740 0.0229 0.0082
1.0002 -0.0001 -0.0006 -0.0144 -0.0720 -0.0299
-0.9999 0.0003 0.9998 -0.0167 0.0958 -0.0325
-0.0003 -0.0002 -0.9992 0.0311 -0.0238 0.0624
-0.9991 1.0001 0.0002 -0.1285 0.0712 0.1005

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26476
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.853
_diffrn_reflns_theta_min         4.227
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  24.00   0.50    0.40    --  -48.70  87.00  59.00  198
  2  ω    -21.00  75.00   0.50    0.40    --   48.70 -87.00 -58.00  192
  3  ω   -112.00 -14.00   0.50    1.60    --  -86.25  87.00  59.00  196
  4  ω     36.00 134.00   0.50    1.60    --  107.75 -87.00 -58.00  196
  5  ω    101.00 178.00   0.50    1.60    --  107.75  87.00  59.00  154
  6  ω   -118.00 -73.00   0.50    0.40    --  -48.70-125.00   0.00   90
  7  ω   -118.00 -73.00   0.50    0.40    --  -48.70-125.00  30.00   90
  8  ω    -26.00  26.00   0.50    0.40    --  -48.70  19.00-180.00  104
  9  ω    -25.00  26.00   0.50    0.40    --   48.70 -19.00-150.00  102
 10  ω   -158.00 -79.00   0.50    1.60    --  -86.25 -87.00 -58.00  158
 11  ω    -51.00 -14.00   0.50    1.60    --  -86.25  45.00-120.00   74
 12  ω    101.00 176.00   0.50    1.60    --  107.75 116.00 -74.79  150
 13  ω     45.00  71.00   0.50    1.60    --  107.75 -61.00 -60.00   52
 14  ω    102.00 150.00   0.50    1.60    --  107.75  30.00 -30.00   96
 15  ω    142.00 173.00   0.50    1.60    --  107.75 125.00-120.00   62
 16  ω     63.00 105.00   0.50    1.60    --  107.75-105.00  13.72   84
 17  ω     41.00  67.00   0.50    1.60    --  107.75 -61.00 120.00   52
 18  ω     46.00  72.00   0.50    1.60    --  107.75 -77.00 -30.00   52
 19  ω     95.00 136.00   0.50    1.60    --  107.75 125.00-120.00   82
 20  ω     37.00  70.00   0.50    1.60    --  107.75 -61.00-150.00   66
 21  ω     50.00  76.00   0.50    1.60    --  107.75-125.00-150.00   52
 22  ω    131.00 177.00   0.50    1.60    --  107.75 125.00-180.00   92
 23  ω     40.00 117.00   0.50    1.60    --  107.75-135.00 151.77  154
 24  ω     60.00 105.00   0.50    1.60    --  107.75 -95.00 -90.00   90
 25  ω    114.00 140.00   0.50    1.60    --  107.75  45.00   0.00   52
 26  ω    143.00 168.00   0.50    1.60    --  107.75  45.00   0.00   50
 27  ω     84.00 111.00   0.50    1.60    --  107.75-125.00-180.00   54
 28  ω     37.00  65.00   0.50    1.60    --  107.75 -57.00-107.27   56
 29  ω     98.00 135.00   0.50    1.60    --  107.75  30.00  30.00   74
 30  ω     44.00  84.00   0.50    1.60    --  107.75 -95.00  90.00   80
 31  ω     95.00 121.00   0.50    1.60    --  107.75 125.00-180.00   52
 32  ω     76.00 101.00   0.50    1.60    --  107.75 -77.00-120.00   50
 33  ω     42.00 106.00   0.50    1.60    --  107.75-105.00  55.78  128
 34  ω     98.00 126.00   0.50    1.60    --  107.75  30.00 150.00   56
 35  ω    131.00 176.00   0.50    1.60    --  107.75  30.00 150.00   90
 36  ω     48.00  81.00   0.50    1.60    --  107.75 -77.00   0.00   66
 37  ω     57.00  83.00   0.50    1.60    --  107.75 -95.00  30.00   52
 38  ω     36.00  63.00   0.50    1.60    --  107.75 -61.00-120.00   54
 39  ω     74.00 104.00   0.50    1.60    --  107.75 -77.00-180.00   60
 40  ω     38.00  71.00   0.50    1.60    --  107.75 -95.00   0.00   66
 41  ω     43.00  77.00   0.50    1.60    --  107.75-125.00-180.00   68
 42  ω    111.00 136.00   0.50    1.60    --  107.75  73.00  49.59   50
 43  ω    134.00 160.00   0.50    1.60    --  107.75  30.00-180.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0143988000
_diffrn_orient_matrix_UB_12      -0.1429129000
_diffrn_orient_matrix_UB_13      -0.0310499000
_diffrn_orient_matrix_UB_21      -0.0719710000
_diffrn_orient_matrix_UB_22      -0.0007380000
_diffrn_orient_matrix_UB_23      0.0238004000
_diffrn_orient_matrix_UB_31      -0.0299406000
_diffrn_orient_matrix_UB_32      0.0705734000
_diffrn_orient_matrix_UB_33      -0.0624379000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4091
_reflns_number_total             4156
_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 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.285
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     306
_refine_ls_number_reflns         4156
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0562
_refine_ls_restrained_S_all      1.283
_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)+(0.0108P)²+10.2680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1260
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-N1 \\sim O5A-N1A
 with sigma of 0.02
 N3-C15 \\sim N3A-C15A
 with sigma of 0.02
 N5-C17 \\sim N5A-C17A
 with sigma of 0.02
 N3A-N3 \\sim C16-C16A
 with sigma of 0.03
 N5-C19 \\sim N5A-C19A
 with sigma of 0.02
 N3-C16 \\sim N3A-C16A
 with sigma of 0.02
 N5-C18 \\sim N5A-C18A
 with sigma of 0.04
 N3-N2 \\sim N3A-N2A
 with sigma of 0.04
 N3-C14 \\sim N3A-C14A
 with sigma of 0.04
 N4A-N5 \\sim N5A-N4
 with sigma of 0.03
 N3A-C15A \\sim C15-N3
 with sigma of 0.03
 N4-C19 \\sim C19A-N5A
 with sigma of 0.03
 N5-N4 \\sim N5A-N4A
 with sigma of 0.03
 O5-C11 \\sim O5A-C11
 with sigma of 0.04
 C18A-N4A \\sim C17-N5
 with sigma of 0.03
 N5-C19 \\sim C19A-N4A
 with sigma of 0.03
 C17A-N5A \\sim C18-N4
 with sigma of 0.03
 N1-O5 \\sim N1A-O5A
 with sigma of 0.03
 N1-C11 \\sim N1A-C11
 with sigma of 0.02
 C11-N1 \\sim N1-N1A
 with sigma of 0.03
 C15A-C14A \\sim C14-C15
 with sigma of 0.03
 N2-C16 \\sim N2A-C16A
 with sigma of 0.02
 N2-C14 \\sim N2A-C14A
 with sigma of 0.02
 C16A-N2 \\sim N2A-C16
 with sigma of 0.03
 C15-C16 \\sim C15A-C16A
 with sigma of 0.04
 C16-C14 \\sim C16A-C14A
 with sigma of 0.04
 C14-C14A \\sim N2A-N2
 with sigma of 0.03
 N2-N2A \\sim C16A-C16
 with sigma of 0.03
 C15-C14 \\sim C15A-C14A
 with sigma of 0.02
 N2-C15 \\sim N2A-C15A
 with sigma of 0.04
 N4-C19 \\sim N4A-C19A
 with sigma of 0.02
 C17-C19 \\sim C17A-C19A
 with sigma of 0.04
 N4-C18 \\sim N4A-C18A
 with sigma of 0.02
 N4-C17 \\sim N4A-C17A
 with sigma of 0.04
 C18A-C17A \\sim C17-C18
 with sigma of 0.03
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C19-C18 \\sim C19A-C18A
 with sigma of 0.04
 C18-C19 \\sim C19A-C17A
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(N3A) = Uanis(N3)
Uanis(N4) = Uanis(N5)
Uanis(N5) = Uanis(N4A)
Uanis(N4A) = Uanis(N5A)
Uanis(O5A) = Uanis(O5)
Uanis(N5A) = Uanis(N4)
Uanis(N1) = Uanis(N1A)
Uanis(C16A) = Uanis(C16)
Uanis(N2A) = Uanis(N2)
Uanis(C15) = Uanis(C15A)
Uanis(C14) = Uanis(C14A)
Uanis(C17) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C17A) = Uanis(C18)
4. Others
 Sof(O5A)=Sof(H5A)=Sof(N1A)=1-FVAR(1)
 Sof(O5)=Sof(H5)=Sof(N1)=FVAR(1)
 Sof(N2A)=Sof(N3A)=Sof(H3E)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(C16A)=
 Sof(H16A)=1-FVAR(2)
 Sof(N2)=Sof(N3)=Sof(H3)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=
 FVAR(2)
 Sof(N4A)=Sof(N5A)=Sof(H5K)=Sof(C17A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=
 Sof(H19A)=1-FVAR(3)
 Sof(N4)=Sof(N5)=Sof(H5D)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=FVAR(3)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5B,H5C), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C8(H8), N3(H3), C14(H14), C15(H15), C16(H16), N3A(H3E), C14A(H14A),
 C15A(H15A), C16A(H16A), C17(H17), C18(H18), C19(H19), C17A(H17A), C18A(H18A),
 C19A(H19A)
5.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
5.d Idealised tetrahedral OH refined as rotating group:
 O5(H5), O5A(H5A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.56872(8) 0.46681(16) 0.42995(7) 0.0269(3) Uani 1 1 d . . . . .
O2 O 0.80230(7) 0.50956(14) 0.41040(6) 0.0201(3) Uani 1 1 d . . . . .
O3 O 0.91951(8) 0.19079(16) 0.35566(8) 0.0307(4) Uani 1 1 d . . . . .
O4 O 0.77898(8) 0.17150(15) 0.33506(7) 0.0268(3) Uani 1 1 d . . . . .
O5 O 0.71498(11) -0.0337(2) 0.27907(11) 0.0266(5) Uani 0.714(3) 1 d D . P A 1
H5 H 0.690714 -0.098898 0.262685 0.040 Uiso 0.714(3) 1 calc R U P A 1
O5A O 0.6337(3) 0.0509(6) 0.2636(3) 0.0266(5) Uani 0.286(3) 1 d D . P A 2
H5A H 0.621682 -0.029927 0.252614 0.040 Uiso 0.286(3) 1 calc R U P A 2
N1 N 0.67429(15) 0.0863(3) 0.28147(13) 0.0238(6) Uani 0.714(3) 1 d D . P A 1
N1A N 0.7016(4) 0.0495(8) 0.2911(4) 0.0238(6) Uani 0.286(3) 1 d D . P A 2
C1 C 0.69490(10) 0.3940(2) 0.37564(9) 0.0207(4) Uani 1 1 d . . . . .
C2 C 0.66495(11) 0.5412(2) 0.37366(11) 0.0262(5) Uani 1 1 d . . . . .
H2A H 0.685953 0.594433 0.410927 0.031 Uiso 1 1 calc R U . . .
H2B H 0.676353 0.588714 0.334389 0.031 Uiso 1 1 calc R U . . .
C3 C 0.58731(12) 0.5379(3) 0.37467(11) 0.0305(5) Uani 1 1 d . . . . .
H3A H 0.569458 0.633900 0.374536 0.037 Uiso 1 1 calc R U . . .
H3B H 0.566048 0.490820 0.335721 0.037 Uiso 1 1 calc R U . . .
C4 C 0.59050(11) 0.3257(2) 0.43046(10) 0.0241(4) Uani 1 1 d . . . . .
H4A H 0.568811 0.278305 0.391747 0.029 Uiso 1 1 calc R U . . .
H4B H 0.575288 0.278296 0.468309 0.029 Uiso 1 1 calc R U . . .
C5 C 0.66808(11) 0.3153(2) 0.43226(9) 0.0209(4) Uani 1 1 d . . . . .
H5B H 0.681525 0.216633 0.430547 0.025 Uiso 1 1 calc R U . . .
H5C H 0.689594 0.354539 0.473013 0.025 Uiso 1 1 calc R U . . .
C6 C 0.77185(10) 0.3943(2) 0.38301(9) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.87248(10) 0.5178(2) 0.41881(9) 0.0210(4) Uani 1 1 d . . . . .
C8 C 0.91202(11) 0.4133(2) 0.40183(10) 0.0244(4) Uani 1 1 d . . . . .
H8 H 0.960540 0.421989 0.409770 0.029 Uiso 1 1 calc R U . . .
C9 C 0.88397(11) 0.2890(2) 0.37216(10) 0.0232(4) Uani 1 1 d . . . . .
C10 C 0.80967(11) 0.2885(2) 0.36335(9) 0.0205(4) Uani 1 1 d . . . . .
C11 C 0.71076(12) 0.1817(2) 0.30978(10) 0.0278(5) Uani 1 1 d D . . . .
C12 C 0.67582(12) 0.3182(3) 0.31175(10) 0.0275(5) Uani 1 1 d . . . . .
H12A H 0.625426 0.304117 0.305470 0.033 Uiso 1 1 calc R U . . .
H12B H 0.688830 0.376628 0.276241 0.033 Uiso 1 1 calc R U . . .
C13 C 0.89628(12) 0.6534(2) 0.44639(11) 0.0264(5) Uani 1 1 d . . . . .
H13A H 0.871233 0.674941 0.483178 0.040 Uiso 1 1 calc R U . . .
H13B H 0.887642 0.725932 0.413963 0.040 Uiso 1 1 calc R U . . .
H13C H 0.945638 0.648594 0.460202 0.040 Uiso 1 1 calc R U . . .
N2 N 0.3711(4) 0.2748(7) 0.2733(3) 0.0284(11) Uani 0.580(10) 1 d D . P B 1
N3 N 0.4127(8) 0.0753(13) 0.3102(9) 0.026(2) Uani 0.580(10) 1 d D . P B 1
H3 H 0.414671 -0.006123 0.329162 0.031 Uiso 0.580(10) 1 calc R U P B 1
C14 C 0.4412(5) 0.2724(8) 0.2696(4) 0.0304(15) Uani 0.580(10) 1 d D . P B 1
H14 H 0.467573 0.346849 0.255476 0.036 Uiso 0.580(10) 1 calc R U P B 1
C15 C 0.4667(6) 0.1466(13) 0.2895(10) 0.0301(16) Uani 0.580(10) 1 d D . P B 1
H15 H 0.512589 0.114757 0.289015 0.036 Uiso 0.580(10) 1 calc R U P B 1
C16 C 0.3561(6) 0.1530(13) 0.2962(9) 0.0290(14) Uani 0.580(10) 1 d D . P B 1
H16 H 0.310791 0.123625 0.302090 0.035 Uiso 0.580(10) 1 calc R U P B 1
N2A N 0.3958(6) 0.2855(10) 0.2662(5) 0.0284(11) Uani 0.420(10) 1 d D . P B 2
N3A N 0.4199(11) 0.0730(19) 0.3001(13) 0.026(2) Uani 0.420(10) 1 d D . P B 2
H3E H 0.413197 -0.013063 0.311830 0.031 Uiso 0.420(10) 1 calc R U P B 2
C14A C 0.4647(6) 0.2560(12) 0.2628(6) 0.0304(15) Uani 0.420(10) 1 d D . P B 2
H14A H 0.495982 0.316300 0.244839 0.036 Uiso 0.420(10) 1 calc R U P B 2
C15A C 0.4818(9) 0.129(2) 0.2884(15) 0.0301(16) Uani 0.420(10) 1 d D . P B 2
H15A H 0.526249 0.089316 0.296286 0.036 Uiso 0.420(10) 1 calc R U P B 2
C16A C 0.3711(8) 0.1720(19) 0.2907(12) 0.0290(14) Uani 0.420(10) 1 d D . P B 2
H16A H 0.324976 0.161587 0.300451 0.035 Uiso 0.420(10) 1 calc R U P B 2
N4 N 0.4269(7) 0.0164(9) 0.5106(5) 0.0258(8) Uani 0.50(2) 1 d D . P C 1
N5 N 0.3163(9) 0.0456(18) 0.5186(11) 0.0258(8) Uani 0.50(2) 1 d D . P C 1
H5D H 0.276(2) 0.039(4) 0.508(2) 0.016(12) Uiso 0.50(2) 1 d . . P C 1
C17 C 0.3522(17) 0.091(6) 0.5744(17) 0.029(2) Uani 0.50(2) 1 d D . P C 1
H17 H 0.332736 0.128945 0.610010 0.035 Uiso 0.50(2) 1 calc R U P C 1
C18 C 0.4201(17) 0.071(5) 0.5700(11) 0.0333(14) Uani 0.50(2) 1 d D . P C 1
H18 H 0.456456 0.092159 0.602060 0.040 Uiso 0.50(2) 1 calc R U P C 1
C19 C 0.3641(8) 0.005(3) 0.4808(7) 0.0230(19) Uani 0.50(2) 1 d D . P C 1
H19 H 0.354038 -0.028057 0.438324 0.028 Uiso 0.50(2) 1 calc R U P C 1
N4A N 0.3258(10) 0.0387(18) 0.5187(12) 0.0258(8) Uani 0.50(2) 1 d D . P C 2
N5A N 0.4394(7) 0.0350(9) 0.5246(5) 0.0258(8) Uani 0.50(2) 1 d D . P C 2
H5K H 0.486(4) 0.024(8) 0.513(4) 0.06(2) Uiso 0.50(2) 1 d . . P C 2
C17A C 0.4208(17) 0.083(5) 0.5820(11) 0.0333(14) Uani 0.50(2) 1 d D . P C 2
H17A H 0.451299 0.111987 0.617680 0.040 Uiso 0.50(2) 1 calc R U P C 2
C18A C 0.3513(17) 0.083(6) 0.5786(17) 0.029(2) Uani 0.50(2) 1 d D . P C 2
H18A H 0.324602 0.109261 0.611946 0.035 Uiso 0.50(2) 1 calc R U P C 2
C19A C 0.3809(7) 0.008(3) 0.4888(8) 0.0230(19) Uani 0.50(2) 1 d D . P C 2
H19A H 0.378604 -0.029599 0.446818 0.028 Uiso 0.50(2) 1 calc R U P C 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
O1 C3 1.429(3) . ?
O1 C4 1.427(3) . ?
O2 C6 1.361(2) . ?
O2 C7 1.368(2) . ?
O3 C9 1.246(3) . ?
O4 C10 1.384(2) . ?
O4 C11 1.388(3) . ?
O5 H5 0.8400 . ?
O5 N1 1.410(3) . ?
O5A H5A 0.8400 . ?
O5A N1A 1.392(8) . ?
N1 C11 1.274(3) . ?
N1A C11 1.342(8) . ?
C1 C2 1.536(3) . ?
C1 C5 1.549(3) . ?
C1 C6 1.497(3) . ?
C1 C12 1.541(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.521(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.517(3) . ?
C5 H5B 0.9900 . ?
C5 H5C 0.9900 . ?
C6 C10 1.351(3) . ?
C7 C8 1.341(3) . ?
C7 C13 1.487(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.435(3) . ?
C9 C10 1.446(3) . ?
C11 C12 1.486(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N2 C14 1.381(6) . ?
N2 C16 1.315(8) . ?
N3 H3 0.8800 . ?
N3 C15 1.369(8) . ?
N3 C16 1.345(9) . ?
C14 H14 0.9500 . ?
C14 C15 1.361(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N2A C14A 1.386(8) . ?
N2A C16A 1.324(11) . ?
N3A H3E 0.8800 . ?
N3A C15A 1.372(11) . ?
N3A C16A 1.352(12) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.364(11) . ?
C15A H15A 0.9500 . ?
C16A H16A 0.9500 . ?
N4 C18 1.376(11) . ?
N4 C19 1.324(10) . ?
N5 H5D 0.80(5) . ?
N5 C17 1.375(13) . ?
N5 C19 1.347(10) . ?
C17 H17 0.9500 . ?
C17 C18 1.352(10) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N4A C18A 1.375(12) . ?
N4A C19A 1.337(11) . ?
N5A H5K 0.98(7) . ?
N5A C17A 1.378(13) . ?
N5A C19A 1.329(10) . ?
C17A H17A 0.9500 . ?
C17A C18A 1.353(10) . ?
C18A H18A 0.9500 . ?
C19A H19A 0.9500 . ?

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
C4 O1 C3 111.32(17) . . ?
C6 O2 C7 119.42(16) . . ?
C10 O4 C11 117.61(17) . . ?
N1 O5 H5 109.5 . . ?
N1A O5A H5A 109.5 . . ?
C11 N1 O5 108.7(3) . . ?
C11 N1A O5A 101.9(6) . . ?
C2 C1 C5 108.40(17) . . ?
C2 C1 C12 110.99(17) . . ?
C6 C1 C2 112.15(17) . . ?
C6 C1 C5 109.78(16) . . ?
C6 C1 C12 103.98(16) . . ?
C12 C1 C5 111.54(17) . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 C1 111.01(18) . . ?
C3 C2 H2A 109.4 . . ?
C3 C2 H2B 109.4 . . ?
O1 C3 C2 111.09(17) . . ?
O1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
O1 C4 C5 111.08(17) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C1 C5 H5B 109.3 . . ?
C1 C5 H5C 109.3 . . ?
C4 C5 C1 111.47(17) . . ?
C4 C5 H5B 109.3 . . ?
C4 C5 H5C 109.3 . . ?
H5B C5 H5C 108.0 . . ?
O2 C6 C1 115.91(17) . . ?
C10 C6 O2 121.20(18) . . ?
C10 C6 C1 122.88(18) . . ?
O2 C7 C13 111.76(18) . . ?
C8 C7 O2 121.37(19) . . ?
C8 C7 C13 126.8(2) . . ?
C7 C8 H8 118.7 . . ?
C7 C8 C9 122.6(2) . . ?
C9 C8 H8 118.7 . . ?
O3 C9 C8 123.9(2) . . ?
O3 C9 C10 122.9(2) . . ?
C8 C9 C10 113.13(18) . . ?
O4 C10 C9 116.33(18) . . ?
C6 C10 O4 121.45(19) . . ?
C6 C10 C9 122.20(19) . . ?
O4 C11 C12 118.63(18) . . ?
N1 C11 O4 126.7(2) . . ?
N1 C11 C12 114.6(2) . . ?
N1A C11 O4 98.0(4) . . ?
N1A C11 C12 143.4(4) . . ?
C1 C12 H12A 109.2 . . ?
C1 C12 H12B 109.2 . . ?
C11 C12 C1 111.97(18) . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C7 C13 H13A 109.5 . . ?
C7 C13 H13B 109.5 . . ?
C7 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C16 N2 C14 105.5(6) . . ?
C15 N3 H3 126.4 . . ?
C16 N3 H3 126.4 . . ?
C16 N3 C15 107.1(7) . . ?
N2 C14 H14 125.3 . . ?
C15 C14 N2 109.4(6) . . ?
C15 C14 H14 125.3 . . ?
N3 C15 H15 127.0 . . ?
C14 C15 N3 106.1(7) . . ?
C14 C15 H15 127.0 . . ?
N2 C16 N3 111.6(7) . . ?
N2 C16 H16 124.2 . . ?
N3 C16 H16 124.2 . . ?
C16A N2A C14A 104.3(9) . . ?
C15A N3A H3E 125.8 . . ?
C16A N3A H3E 125.8 . . ?
C16A N3A C15A 108.5(11) . . ?
N2A C14A H14A 124.3 . . ?
C15A C14A N2A 111.3(9) . . ?
C15A C14A H14A 124.3 . . ?
N3A C15A H15A 128.0 . . ?
C14A C15A N3A 104.0(10) . . ?
C14A C15A H15A 128.0 . . ?
N2A C16A N3A 111.1(10) . . ?
N2A C16A H16A 124.4 . . ?
N3A C16A H16A 124.4 . . ?
C19 N4 C18 106.8(12) . . ?
C17 N5 H5D 131(4) . . ?
C19 N5 H5D 123(4) . . ?
C19 N5 C17 105.7(16) . . ?
N5 C17 H17 125.8 . . ?
C18 C17 N5 108(2) . . ?
C18 C17 H17 125.8 . . ?
N4 C18 H18 126.2 . . ?
C17 C18 N4 107.6(19) . . ?
C17 C18 H18 126.2 . . ?
N4 C19 N5 111.3(7) . . ?
N4 C19 H19 124.3 . . ?
N5 C19 H19 124.3 . . ?
C19A N4A C18A 105.6(16) . . ?
C17A N5A H5K 127(5) . . ?
C19A N5A H5K 127(5) . . ?
C19A N5A C17A 105.9(12) . . ?
N5A C17A H17A 126.0 . . ?
C18A C17A N5A 107.9(19) . . ?
C18A C17A H17A 126.0 . . ?
N4A C18A H18A 125.8 . . ?
C17A C18A N4A 108(2) . . ?
C17A C18A H18A 125.8 . . ?
N4A C19A H19A 123.9 . . ?
N5A C19A N4A 112.1(7) . . ?
N5A C19A H19A 123.9 . . ?

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
N5 H5D N5 0.80(5) 1.83(5) 2.63(4) 174(5) 2_556 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 C4 C5 C1 -56.4(2) . . . . ?
O2 C6 C10 O4 -179.54(17) . . . . ?
O2 C6 C10 C9 2.2(3) . . . . ?
O2 C7 C8 C9 2.0(3) . . . . ?
O3 C9 C10 O4 -0.1(3) . . . . ?
O3 C9 C10 C6 178.2(2) . . . . ?
O4 C11 C12 C1 -40.8(3) . . . . ?
O5 N1 C11 O4 -0.6(4) . . . . ?
O5 N1 C11 C12 175.85(19) . . . . ?
O5A N1A C11 O4 -178.9(5) . . . . ?
O5A N1A C11 C12 1.0(10) . . . . ?
N1 C11 C12 C1 142.4(2) . . . . ?
N1A C11 C12 C1 139.3(6) . . . . ?
C1 C2 C3 O1 57.6(2) . . . . ?
C1 C6 C10 O4 -0.3(3) . . . . ?
C1 C6 C10 C9 -178.53(18) . . . . ?
C2 C1 C5 C4 51.1(2) . . . . ?
C2 C1 C6 O2 24.1(2) . . . . ?
C2 C1 C6 C10 -155.18(19) . . . . ?
C2 C1 C12 C11 173.44(18) . . . . ?
C3 O1 C4 C5 61.3(2) . . . . ?
C4 O1 C3 C2 -62.0(2) . . . . ?
C5 C1 C2 C3 -51.4(2) . . . . ?
C5 C1 C6 O2 -96.5(2) . . . . ?
C5 C1 C6 C10 84.3(2) . . . . ?
C5 C1 C12 C11 -65.6(2) . . . . ?
C6 O2 C7 C8 -1.4(3) . . . . ?
C6 O2 C7 C13 177.22(17) . . . . ?
C6 C1 C2 C3 -172.79(17) . . . . ?
C6 C1 C5 C4 173.91(17) . . . . ?
C6 C1 C12 C11 52.7(2) . . . . ?
C7 O2 C6 C1 179.98(16) . . . . ?
C7 O2 C6 C10 -0.7(3) . . . . ?
C7 C8 C9 O3 179.7(2) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 O4 -179.87(17) . . . . ?
C8 C9 C10 C6 -1.5(3) . . . . ?
C10 O4 C11 N1 179.2(2) . . . . ?
C10 O4 C11 N1A -177.2(4) . . . . ?
C10 O4 C11 C12 2.8(3) . . . . ?
C11 O4 C10 C6 19.2(3) . . . . ?
C11 O4 C10 C9 -162.41(18) . . . . ?
C12 C1 C2 C3 71.4(2) . . . . ?
C12 C1 C5 C4 -71.4(2) . . . . ?
C12 C1 C6 O2 144.10(17) . . . . ?
C12 C1 C6 C10 -35.2(3) . . . . ?
C13 C7 C8 C9 -176.4(2) . . . . ?
N2 C14 C15 N3 -5(2) . . . . ?
C14 N2 C16 N3 2.9(18) . . . . ?
C15 N3 C16 N2 -6(2) . . . . ?
C16 N2 C14 C15 1.2(15) . . . . ?
C16 N3 C15 C14 6(2) . . . . ?
N2A C14A C15A N3A 8(3) . . . . ?
C14A N2A C16A N3A -2(3) . . . . ?
C15A N3A C16A N2A 7(4) . . . . ?
C16A N2A C14A C15A -3(2) . . . . ?
C16A N3A C15A C14A -9(3) . . . . ?
N5 C17 C18 N4 1(6) . . . . ?
C17 N5 C19 N4 3(4) . . . . ?
C18 N4 C19 N5 -2(3) . . . . ?
C19 N4 C18 C17 0(5) . . . . ?
C19 N5 C17 C18 -2(5) . . . . ?
N5A C17A C18A N4A -2(6) . . . . ?
C17A N5A C19A N4A 2(3) . . . . ?
C18A N4A C19A N5A -3(4) . . . . ?
C19A N4A C18A C17A 3(5) . . . . ?
C19A N5A C17A C18A 0(5) . . . . ?

_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.797
####################################################################### 
# 
# 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_c6t2tt
_database_code_depnum_ccdc_archive 'CCDC 2270302'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-03
_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        ?
_chemical_formula_moiety         'C22 H23 N3 O4 S, C2 H6 O'
_chemical_formula_sum            'C24 H29 N3 O5 S'
_chemical_formula_weight         471.56
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H21N3O3S
_chemical_oxdiff_usercomment     C6T2TT
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.03440(10)
_cell_length_b                   10.70520(10)
_cell_length_c                   11.26660(10)
_cell_angle_alpha                70.4960(10)
_cell_angle_beta                 89.3540(10)
_cell_angle_gamma                79.0940(10)
_cell_volume                     1118.45(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    30944
_cell_measurement_temperature    99.97(10)
_cell_measurement_theta_max      77.5900
_cell_measurement_theta_min      4.1280
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.735
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74689
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.53a (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_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            34127
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.920
_diffrn_reflns_theta_min         4.169
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(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 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -4.00   0.50    0.15    --  -48.79 113.00 -43.00  156
  2  ω     26.00  86.00   0.50    0.15    --   48.79-113.00-135.00  120
  3  ω    -83.00 -18.00   0.50    0.60    --  -86.25 113.00 -43.00  130
  4  ω   -154.00 -81.00   0.50    0.60    --  -86.25-113.00-135.00  146
  5  ω     40.00 108.00   0.50    0.60    --  107.75-113.00-135.00  136
  6  ω    102.00 176.00   0.50    0.60    --  107.75 113.00 -43.00  148
  7  ω    -26.00  26.00   0.50    0.15    --  -48.79  19.00-150.00  104
  8  ω    -26.00  26.00   0.50    0.15    --  -48.79  19.00 -60.00  104
  9  ω    -43.00  23.00   0.50    0.15    --  -48.79  38.00  60.00  132
 10  ω   -118.00 -73.00   0.50    0.15    --  -48.79-125.00  30.00   90
 11  ω    -63.00  23.00   0.50    0.15    --  -48.79  57.00 -90.00  172
 12  ω     35.00 120.00   0.50    0.15    --   48.79  57.00 -30.00  170
 13  ω   -158.00 -71.00   0.50    0.60    --  -86.25 -61.00 -70.69  174
 14  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00 120.00   70
 15  ω     97.00 178.00   0.50    0.60    --  107.75  45.00 150.00  162
 16  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00 -90.00  138
 17  ω     97.00 178.00   0.50    0.60    --  107.75  45.00-120.00  162
 18  ω     95.00 177.00   0.50    0.60    --  107.75 125.00 -30.00  164
 19  ω     95.00 177.00   0.50    0.60    --  107.75 125.00 -60.00  164
 20  ω     39.00 111.00   0.50    0.60    --  107.75-125.00  90.00  144
 21  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00 150.00   70
 22  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00   0.00  138
 23  ω     39.00 111.00   0.50    0.60    --  107.75-125.00  60.00  144
 24  ω     97.00 178.00   0.50    0.60    --  107.75  15.00-120.00  162
 25  ω     36.00 166.00   0.50    0.60    --  107.75   0.00-150.00  260
 26  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00 -30.00  138
 27  ω     97.00 178.00   0.50    0.60    --  107.75  30.00 120.00  162
 28  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00  60.00  138
 29  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00  30.00   70
 30  ω     38.00 107.00   0.50    0.60    --  107.75-102.00 -22.98  138
 31  ω     39.00 111.00   0.50    0.60    --  107.75-125.00-120.00  144
 32  ω     97.00 178.00   0.50    0.60    --  107.75  30.00 -60.00  162
 33  ω     39.00 111.00   0.50    0.60    --  107.75-125.00 120.00  144
 34  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00-150.00  138
 35  ω     39.00 111.00   0.50    0.60    --  107.75-125.00 -60.00  144
 36  ω     39.00 111.00   0.50    0.60    --  107.75-125.00 150.00  144
 37  ω     97.00 178.00   0.50    0.60    --  107.75  30.00  60.00  162
 38  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00  90.00  138
 39  ω     39.00 111.00   0.50    0.60    --  107.75-125.00-180.00  144
 40  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00-180.00  138
 41  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00 -60.00  138
 42  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00 -60.00   70
 43  ω     95.00 177.00   0.50    0.60    --  107.75 125.00  30.00  164
 44  ω     86.00 178.00   0.50    0.60    --  107.75  77.00  90.00  184
 45  ω     36.00  71.00   0.50    0.60    --  107.75 -61.00-150.00   70
 46  ω     97.00 178.00   0.50    0.60    --  107.75  15.00 -60.00  162
 47  ω     95.00 177.00   0.50    0.60    --  107.75 125.00 150.00  164
 48  ω     86.00 178.00   0.50    0.60    --  107.75  77.00 120.00  184
 49  ω     36.00 105.00   0.50    0.60    --  107.75 -77.00 150.00  138
 50  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00 -90.00  138
 51  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00 -30.00  138
 52  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00   0.00  138
 53  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00  60.00  138
 54  ω     39.00 108.00   0.50    0.60    --  107.75-110.00 106.96  138
 55  ω     36.00 106.00   0.50    0.60    --  107.75 -90.00-110.08  140
 56  ω     36.00 105.00   0.50    0.60    --  107.75 -95.00 150.00  138
 57  ω     99.00 137.00   0.50    0.60    --  107.75  45.00 -30.00   76
 58  ω     43.00  73.00   0.50    0.60    --  107.75-125.00  30.00   60
 59  ω     38.00 106.00   0.50    0.60    --  107.75-101.00 -98.92  136
 60  ω    108.00 134.00   0.50    0.60    --  107.75  15.00 -30.00   52
 61  ω    101.00 128.00   0.50    0.60    --  107.75  15.00 150.00   54
 62  ω    103.00 178.00   0.50    0.60    --  107.75  42.00 169.94  150
 63  ω    138.00 164.00   0.50    0.60    --  107.75 125.00  90.00   52
 64  ω     36.00  67.00   0.50    0.60    --  107.75 -61.00   0.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0372054000
_diffrn_orient_matrix_UB_12      0.1470165000
_diffrn_orient_matrix_UB_13      -0.0017978000
_diffrn_orient_matrix_UB_21      -0.0202877000
_diffrn_orient_matrix_UB_22      -0.0512461000
_diffrn_orient_matrix_UB_23      0.1427055000
_diffrn_orient_matrix_UB_31      0.1507546000
_diffrn_orient_matrix_UB_32      -0.0024341000
_diffrn_orient_matrix_UB_33      0.0272216000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4689
_reflns_number_total             4730
_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 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.53a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.53a (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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0016(3)
_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   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4730
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.051
_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)+(0.0502P)²+0.4790P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_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 C(H,H,H) groups
2. Restrained distances
 C5-O1A \\sim C5-O1B
 with sigma of 0.03
 O1A-C8A \\sim O1B-C8B
 with sigma of 0.03
3. Uiso/Uaniso restraints and constraints
Uanis(C8A) = Uanis(C8B)
Uanis(O1A) = Uanis(O1B)
4. Others
 Sof(O1B)=Sof(C8B)=Sof(H8BA)=Sof(H8BB)=Sof(H8BC)=1-FVAR(1)
 Sof(O1A)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=Sof(H8AC)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C23(H23A,H23B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C20(H20)
5.c Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C8B(H8BA,H8BB,H8BC), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
S1 S 0.50559(3) 0.79401(3) 0.18783(2) 0.01579(9) Uani 1 1 d . . . . .
O1A O 0.8389(17) 1.1277(18) 0.1068(12) 0.0178(11) Uani 0.58(2) 1 d D . P A 1
O1B O 0.845(3) 1.135(3) 0.1201(16) 0.0178(11) Uani 0.42(2) 1 d D . P A 2
O2 O 0.22482(8) 0.48356(8) 0.45818(7) 0.01599(17) Uani 1 1 d . . . . .
O3 O 0.04347(8) 0.21708(8) 0.46654(7) 0.01444(17) Uani 1 1 d . . . . .
O4 O 0.14195(9) 0.41295(8) 0.69691(8) 0.01820(18) Uani 1 1 d . . . . .
N1 N 0.49066(10) 0.82692(10) 0.40900(9) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.36822(10) 0.66903(10) 0.38456(9) 0.0172(2) Uani 1 1 d . . . . .
H2 H 0.3326(19) 0.6567(19) 0.4600(18) 0.035(5) Uiso 1 1 d . . . . .
N3 N 0.32028(10) 0.62393(10) 0.29501(9) 0.0150(2) Uani 1 1 d . . . . .
C1 C 0.44897(11) 0.76186(11) 0.34226(10) 0.0149(2) Uani 1 1 d . . . . .
C2 C 0.57677(11) 0.90887(11) 0.33853(11) 0.0147(2) Uani 1 1 d . . . . .
C3 C 0.59817(11) 0.90419(11) 0.21681(11) 0.0146(2) Uani 1 1 d . . . . .
C4 C 0.68258(11) 0.97861(11) 0.13508(11) 0.0158(2) Uani 1 1 d . . . . .
H4 H 0.694310 0.974811 0.052483 0.019 Uiso 1 1 calc R U . . .
C5 C 0.74877(11) 1.05852(11) 0.17955(11) 0.0159(2) Uani 1 1 d D . . . .
C6 C 0.72647(12) 1.06806(11) 0.29933(11) 0.0165(2) Uani 1 1 d . . . . .
H6 H 0.770688 1.125463 0.326722 0.020 Uiso 1 1 calc R U . . .
C7 C 0.64068(11) 0.99483(11) 0.37861(11) 0.0158(2) Uani 1 1 d . . . . .
H7 H 0.625312 1.002791 0.459361 0.019 Uiso 1 1 calc R U . . .
C8A C 0.8593(13) 1.1318(12) -0.0182(10) 0.0304(14) Uani 0.58(2) 1 d D . P A 1
H8AA H 0.773137 1.170265 -0.068638 0.046 Uiso 0.58(2) 1 calc R U P A 1
H8AB H 0.892787 1.039938 -0.018991 0.046 Uiso 0.58(2) 1 calc R U P A 1
H8AC H 0.926263 1.187975 -0.053963 0.046 Uiso 0.58(2) 1 calc R U P A 1
C8B C 0.8318(16) 1.1596(16) -0.0131(14) 0.0304(14) Uani 0.42(2) 1 d D . P A 2
H8BA H 0.738472 1.205135 -0.044737 0.046 Uiso 0.42(2) 1 calc R U P A 2
H8BB H 0.852897 1.073455 -0.028827 0.046 Uiso 0.42(2) 1 calc R U P A 2
H8BC H 0.895006 1.217051 -0.056617 0.046 Uiso 0.42(2) 1 calc R U P A 2
C9 C 0.24876(11) 0.53307(11) 0.33240(10) 0.0137(2) Uani 1 1 d . . . . .
C10 C 0.17962(11) 0.48931(11) 0.24049(10) 0.0141(2) Uani 1 1 d . . . . .
H10A H 0.232437 0.503305 0.163971 0.017 Uiso 1 1 calc R U . . .
H10B H 0.088583 0.548086 0.215242 0.017 Uiso 1 1 calc R U . . .
C11 C 0.16256(11) 0.34017(11) 0.29055(10) 0.0134(2) Uani 1 1 d . . . . .
C12 C 0.05459(12) 0.32100(12) 0.20525(10) 0.0163(2) Uani 1 1 d . . . . .
H12A H 0.031310 0.230861 0.244800 0.020 Uiso 1 1 calc R U . . .
H12B H -0.028987 0.390077 0.197045 0.020 Uiso 1 1 calc R U . . .
C13 C 0.10582(12) 0.33320(12) 0.07414(11) 0.0190(2) Uani 1 1 d . . . . .
H13A H 0.035528 0.317278 0.022903 0.023 Uiso 1 1 calc R U . . .
H13B H 0.121384 0.426005 0.031664 0.023 Uiso 1 1 calc R U . . .
C14 C 0.23764(14) 0.23193(12) 0.08162(12) 0.0227(3) Uani 1 1 d . . . . .
H14A H 0.270050 0.245177 -0.004229 0.027 Uiso 1 1 calc R U . . .
H14B H 0.220308 0.138878 0.116836 0.027 Uiso 1 1 calc R U . . .
C15 C 0.34706(13) 0.24957(12) 0.16455(11) 0.0208(2) Uani 1 1 d . . . . .
H15A H 0.372042 0.338770 0.124020 0.025 Uiso 1 1 calc R U . . .
H15B H 0.429316 0.178962 0.172751 0.025 Uiso 1 1 calc R U . . .
C16 C 0.29723(11) 0.23957(11) 0.29576(11) 0.0168(2) Uani 1 1 d . . . . .
H16A H 0.367919 0.257642 0.344948 0.020 Uiso 1 1 calc R U . . .
H16B H 0.283704 0.146390 0.340140 0.020 Uiso 1 1 calc R U . . .
C17 C 0.11771(11) 0.31571(11) 0.42313(10) 0.0134(2) Uani 1 1 d . . . . .
C18 C 0.15024(11) 0.38256(11) 0.49783(10) 0.0137(2) Uani 1 1 d . . . . .
C19 C 0.11188(11) 0.35206(11) 0.62752(10) 0.0144(2) Uani 1 1 d . . . . .
C20 C 0.03311(12) 0.24725(11) 0.66538(10) 0.0155(2) Uani 1 1 d . . . . .
H20 H 0.003159 0.220601 0.748821 0.019 Uiso 1 1 calc R U . . .
C21 C 0.00054(11) 0.18579(11) 0.58620(10) 0.0151(2) Uani 1 1 d . . . . .
C22 C -0.08421(13) 0.08043(12) 0.61473(11) 0.0192(2) Uani 1 1 d . . . . .
H22A H -0.163230 0.111937 0.554552 0.029 Uiso 1 1 calc R U . . .
H22B H -0.115057 0.063011 0.700566 0.029 Uiso 1 1 calc R U . . .
H22C H -0.030180 -0.003051 0.607883 0.029 Uiso 1 1 calc R U . . .
O5 O 0.26206(9) 0.64052(9) 0.62529(8) 0.01847(18) Uani 1 1 d . . . . .
H5 H 0.220(2) 0.575(2) 0.6423(18) 0.039(5) Uiso 1 1 d . . . . .
C23 C 0.38121(12) 0.59795(13) 0.70791(12) 0.0224(3) Uani 1 1 d . . . . .
H23A H 0.431022 0.673163 0.689800 0.027 Uiso 1 1 calc R U . . .
H23B H 0.441424 0.521527 0.691489 0.027 Uiso 1 1 calc R U . . .
C24 C 0.34838(15) 0.55467(14) 0.84514(13) 0.0289(3) Uani 1 1 d . . . . .
H24A H 0.291735 0.631069 0.862664 0.043 Uiso 1 1 calc R U . . .
H24B H 0.432933 0.524774 0.898188 0.043 Uiso 1 1 calc R U . . .
H24C H 0.299187 0.480085 0.863601 0.043 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
S1 C1 1.7665(11) . ?
S1 C3 1.7434(11) . ?
O1A C5 1.367(11) . ?
O1A C8A 1.409(10) . ?
O1B C5 1.402(16) . ?
O1B C8B 1.437(16) . ?
O2 C9 1.3732(13) . ?
O2 C18 1.3801(13) . ?
O3 C17 1.3614(13) . ?
O3 C21 1.3621(13) . ?
O4 C19 1.2438(14) . ?
N1 C1 1.3010(15) . ?
N1 C2 1.3975(14) . ?
N2 H2 0.897(19) . ?
N2 N3 1.3807(13) . ?
N2 C1 1.3605(15) . ?
N3 C9 1.2737(15) . ?
C2 C3 1.4016(16) . ?
C2 C7 1.4032(15) . ?
C3 C4 1.3956(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3902(16) . ?
C5 C6 1.3995(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3871(16) . ?
C7 H7 0.9500 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9 C10 1.4954(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5480(14) . ?
C11 C12 1.5424(15) . ?
C11 C16 1.5486(15) . ?
C11 C17 1.5069(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5306(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5267(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5276(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5313(16) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.3505(16) . ?
C18 C19 1.4513(15) . ?
C19 C20 1.4402(15) . ?
C20 H20 0.9500 . ?
C20 C21 1.3474(16) . ?
C21 C22 1.4877(15) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
O5 H5 0.85(2) . ?
O5 C23 1.4280(15) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5105(18) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
C3 S1 C1 87.94(5) . . ?
C5 O1A C8A 122.4(11) . . ?
C5 O1B C8B 108.5(13) . . ?
C9 O2 C18 118.57(9) . . ?
C17 O3 C21 119.87(9) . . ?
C1 N1 C2 109.20(10) . . ?
N3 N2 H2 122.8(12) . . ?
C1 N2 H2 119.5(12) . . ?
C1 N2 N3 115.80(9) . . ?
C9 N3 N2 117.41(10) . . ?
N1 C1 S1 117.20(9) . . ?
N1 C1 N2 124.46(10) . . ?
N2 C1 S1 118.32(8) . . ?
N1 C2 C3 115.86(10) . . ?
N1 C2 C7 125.79(10) . . ?
C3 C2 C7 118.35(10) . . ?
C2 C3 S1 109.79(8) . . ?
C4 C3 S1 127.24(9) . . ?
C4 C3 C2 122.97(10) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.24(10) . . ?
C5 C4 H4 121.4 . . ?
O1A C5 C4 120.1(6) . . ?
O1A C5 C6 118.9(6) . . ?
C4 C5 O1B 128.3(7) . . ?
C4 C5 C6 121.03(10) . . ?
C6 C5 O1B 110.6(7) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.88(10) . . ?
C7 C6 H6 119.6 . . ?
C2 C7 H7 120.3 . . ?
C6 C7 C2 119.45(10) . . ?
C6 C7 H7 120.3 . . ?
O1A C8A H8AA 109.5 . . ?
O1A C8A H8AB 109.5 . . ?
O1A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
O1B C8B H8BA 109.5 . . ?
O1B C8B H8BB 109.5 . . ?
O1B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O2 C9 C10 119.40(9) . . ?
N3 C9 O2 119.21(10) . . ?
N3 C9 C10 121.11(10) . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.74(9) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 C16 112.63(9) . . ?
C12 C11 C10 108.91(9) . . ?
C12 C11 C16 109.70(9) . . ?
C17 C11 C10 105.69(9) . . ?
C17 C11 C12 111.58(9) . . ?
C17 C11 C16 108.32(9) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.39(9) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.54(10) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 C15 110.86(10) . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.17(10) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
C11 C16 H16A 109.1 . . ?
C11 C16 H16B 109.1 . . ?
C15 C16 C11 112.58(9) . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
O3 C17 C11 115.55(9) . . ?
C18 C17 O3 120.69(10) . . ?
C18 C17 C11 123.74(10) . . ?
O2 C18 C19 114.43(9) . . ?
C17 C18 O2 122.92(10) . . ?
C17 C18 C19 122.64(10) . . ?
O4 C19 C18 122.95(10) . . ?
O4 C19 C20 124.07(10) . . ?
C20 C19 C18 112.97(10) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 C19 122.09(10) . . ?
C21 C20 H20 119.0 . . ?
O3 C21 C22 112.19(10) . . ?
C20 C21 O3 121.69(10) . . ?
C20 C21 C22 126.11(10) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 O5 H5 108.1(13) . . ?
O5 C23 H23A 109.1 . . ?
O5 C23 H23B 109.1 . . ?
O5 C23 C24 112.30(10) . . ?
H23A C23 H23B 107.9 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

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
N2 H2 O5 0.897(19) 1.95(2) 2.8441(13) 175.6(18) . yes
O5 H5 O4 0.85(2) 1.95(2) 2.7955(12) 172.9(19) . 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
S1 C3 C4 C5 -178.77(9) . . . . ?
O1A C5 C6 C7 -177.1(10) . . . . ?
O1B C5 C6 C7 -176.4(13) . . . . ?
O2 C9 C10 C11 -36.41(14) . . . . ?
O2 C18 C19 O4 0.94(16) . . . . ?
O2 C18 C19 C20 179.42(9) . . . . ?
O3 C17 C18 O2 -179.78(9) . . . . ?
O3 C17 C18 C19 1.51(17) . . . . ?
O4 C19 C20 C21 178.62(11) . . . . ?
N1 C2 C3 S1 0.62(12) . . . . ?
N1 C2 C3 C4 -179.20(10) . . . . ?
N1 C2 C7 C6 178.42(10) . . . . ?
N2 N3 C9 O2 -0.98(15) . . . . ?
N2 N3 C9 C10 173.04(10) . . . . ?
N3 N2 C1 S1 -9.94(14) . . . . ?
N3 N2 C1 N1 171.84(10) . . . . ?
N3 C9 C10 C11 149.59(10) . . . . ?
C1 S1 C3 C2 -0.97(8) . . . . ?
C1 S1 C3 C4 178.84(11) . . . . ?
C1 N1 C2 C3 0.30(14) . . . . ?
C1 N1 C2 C7 179.46(11) . . . . ?
C1 N2 N3 C9 177.32(10) . . . . ?
C2 N1 C1 S1 -1.12(13) . . . . ?
C2 N1 C1 N2 177.11(10) . . . . ?
C2 C3 C4 C5 1.01(17) . . . . ?
C3 S1 C1 N1 1.27(9) . . . . ?
C3 S1 C1 N2 -177.07(10) . . . . ?
C3 C2 C7 C6 -2.43(16) . . . . ?
C3 C4 C5 O1A 176.2(10) . . . . ?
C3 C4 C5 O1B 175.3(15) . . . . ?
C3 C4 C5 C6 -2.76(17) . . . . ?
C4 C5 C6 C7 1.93(17) . . . . ?
C5 C6 C7 C2 0.76(17) . . . . ?
C7 C2 C3 S1 -178.61(8) . . . . ?
C7 C2 C3 C4 1.57(17) . . . . ?
C8A O1A C5 C4 6(2) . . . . ?
C8A O1A C5 C6 -175.0(12) . . . . ?
C8B O1B C5 C4 21(3) . . . . ?
C8B O1B C5 C6 -161.0(14) . . . . ?
C9 O2 C18 C17 10.57(16) . . . . ?
C9 O2 C18 C19 -170.63(9) . . . . ?
C9 C10 C11 C12 162.95(9) . . . . ?
C9 C10 C11 C16 -75.13(12) . . . . ?
C9 C10 C11 C17 42.96(12) . . . . ?
C10 C11 C12 C13 68.92(12) . . . . ?
C10 C11 C16 C15 -67.27(12) . . . . ?
C10 C11 C17 O3 153.43(9) . . . . ?
C10 C11 C17 C18 -28.36(14) . . . . ?
C11 C12 C13 C14 57.05(12) . . . . ?
C11 C17 C18 O2 2.10(17) . . . . ?
C11 C17 C18 C19 -176.61(10) . . . . ?
C12 C11 C16 C15 54.21(12) . . . . ?
C12 C11 C17 O3 35.21(13) . . . . ?
C12 C11 C17 C18 -146.58(11) . . . . ?
C12 C13 C14 C15 -56.67(13) . . . . ?
C13 C14 C15 C16 55.21(13) . . . . ?
C14 C15 C16 C11 -54.92(13) . . . . ?
C16 C11 C12 C13 -54.77(12) . . . . ?
C16 C11 C17 O3 -85.64(11) . . . . ?
C16 C11 C17 C18 92.57(12) . . . . ?
C17 O3 C21 C20 -2.09(16) . . . . ?
C17 O3 C21 C22 177.36(9) . . . . ?
C17 C11 C12 C13 -174.80(9) . . . . ?
C17 C11 C16 C15 176.21(9) . . . . ?
C17 C18 C19 O4 179.75(11) . . . . ?
C17 C18 C19 C20 -1.77(15) . . . . ?
C18 O2 C9 N3 -178.28(10) . . . . ?
C18 O2 C9 C10 7.60(14) . . . . ?
C18 C19 C20 C21 0.16(16) . . . . ?
C19 C20 C21 O3 1.74(17) . . . . ?
C19 C20 C21 C22 -177.64(11) . . . . ?
C21 O3 C17 C11 178.73(9) . . . . ?
C21 O3 C17 C18 0.46(15) . . . . ?

_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 1.325
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_KJC6PHYP
_database_code_depnum_ccdc_archive 'CCDC 2270304'
loop_
_audit_author_name
_audit_author_address
'Egor Igorevich Tuzharov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H24 N2 O4'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.1768(3)
_cell_length_b                   9.4700(3)
_cell_length_c                   21.5491(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1872.71(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9812
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      33.74

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.867
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.302
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_process_details   
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.5
_diffrn_source_size              '0.6 mm, fine-focus'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method       'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean 7.31
_diffrn_reflns_number            54599
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.349
_diffrn_reflns_theta_max         33.738
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7492
_reflns_number_gt                7058
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.999

_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       'APEX3 (Bruker, 2019)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'SAINT (Bruker, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material  
'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.2009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2990 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7492
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0889
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.48537(8) 0.36520(8) 0.36531(4) 0.01393(14) Uani 1 1 d . . . . .
O2 O 0.55200(10) 0.00354(9) 0.32279(5) 0.02041(17) Uani 1 1 d . . . . .
H3 H 0.618(2) -0.032(2) 0.3003(9) 0.026(5) Uiso 1 1 d . . . . .
O3 O 0.80853(9) 0.13192(9) 0.29057(4) 0.01941(16) Uani 1 1 d . . . . .
O4 O 0.30965(8) 0.31747(9) 0.25128(4) 0.01794(16) Uani 1 1 d . . . . .
N1 N 0.07040(10) 0.25925(10) 0.25160(5) 0.01598(17) Uani 1 1 d . . . . .
H1 H -0.003(3) 0.213(2) 0.2684(11) 0.045(6) Uiso 1 1 d . . . . .
N2 N 0.03526(10) 0.36773(10) 0.20925(5) 0.01590(16) Uani 1 1 d . . . . .
H2 H 0.103(2) 0.431(2) 0.2095(9) 0.025(4) Uiso 1 1 d . . . . .
C1 C 0.46453(10) 0.22344(10) 0.35752(5) 0.01153(16) Uani 1 1 d . . . . .
C2 C 0.57227(11) 0.14359(11) 0.33175(5) 0.01310(17) Uani 1 1 d . . . . .
C3 C 0.70801(11) 0.20754(11) 0.31269(5) 0.01338(17) Uani 1 1 d . . . . .
C4 C 0.71856(11) 0.35731(12) 0.31990(5) 0.01495(17) Uani 1 1 d . . . . .
H4 H 0.803382 0.405632 0.306200 0.018 Uiso 1 1 calc R U . . .
C5 C 0.60786(12) 0.43028(12) 0.34623(5) 0.01572(19) Uani 1 1 d . . . . .
C6 C 0.31367(10) 0.17307(11) 0.37630(5) 0.01216(16) Uani 1 1 d . . . . .
C7 C 0.32201(12) 0.04430(12) 0.42068(5) 0.01603(18) Uani 1 1 d . . . . .
H7A H 0.223482 0.002897 0.425051 0.019 Uiso 1 1 calc R U . . .
H7B H 0.385983 -0.028359 0.401996 0.019 Uiso 1 1 calc R U . . .
C8 C 0.38006(13) 0.08207(15) 0.48500(6) 0.0219(2) Uani 1 1 d . . . . .
H8A H 0.482337 0.114290 0.481372 0.026 Uiso 1 1 calc R U . . .
H8B H 0.378715 -0.003085 0.511644 0.026 Uiso 1 1 calc R U . . .
C9 C 0.28885(14) 0.19815(15) 0.51530(6) 0.0236(2) Uani 1 1 d . . . . .
H9A H 0.188854 0.162878 0.522846 0.028 Uiso 1 1 calc R U . . .
H9B H 0.332165 0.224069 0.555805 0.028 Uiso 1 1 calc R U . . .
C10 C 0.28279(13) 0.32801(14) 0.47352(5) 0.0197(2) Uani 1 1 d . . . . .
H10A H 0.381604 0.369046 0.469697 0.024 Uiso 1 1 calc R U . . .
H10B H 0.218586 0.399985 0.492556 0.024 Uiso 1 1 calc R U . . .
C11 C 0.22510(11) 0.29013(12) 0.40881(5) 0.01553(18) Uani 1 1 d . . . . .
H11A H 0.226460 0.375899 0.382550 0.019 Uiso 1 1 calc R U . . .
H11B H 0.122536 0.258873 0.412581 0.019 Uiso 1 1 calc R U . . .
C12 C 0.23232(11) 0.12510(11) 0.31697(5) 0.01394(17) Uani 1 1 d . . . . .
H12A H 0.288882 0.048771 0.296841 0.017 Uiso 1 1 calc R U . . .
H12B H 0.136512 0.085583 0.328980 0.017 Uiso 1 1 calc R U . . .
C13 C 0.20860(11) 0.24253(11) 0.27060(5) 0.01330(17) Uani 1 1 d . . . . .
C14 C 0.00375(12) 0.32041(11) 0.14836(5) 0.01562(18) Uani 1 1 d . . . . .
C15 C 0.06754(13) 0.38506(13) 0.09706(6) 0.0207(2) Uani 1 1 d . . . . .
H15 H 0.139035 0.456423 0.102818 0.025 Uiso 1 1 calc R U . . .
C16 C 0.02664(15) 0.34521(15) 0.03731(6) 0.0246(2) Uani 1 1 d . . . . .
H16 H 0.071100 0.389128 0.002489 0.030 Uiso 1 1 calc R U . . .
C17 C -0.07877(18) 0.24164(14) 0.02820(6) 0.0265(3) Uani 1 1 d . . . . .
H17 H -0.106924 0.215152 -0.012600 0.032 Uiso 1 1 calc R U . . .
C18 C -0.14222(18) 0.17755(14) 0.07934(7) 0.0287(3) Uani 1 1 d . . . . .
H18 H -0.214365 0.106904 0.073374 0.034 Uiso 1 1 calc R U . . .
C19 C -0.10160(16) 0.21536(13) 0.13928(6) 0.0237(2) Uani 1 1 d . . . . .
H19 H -0.145193 0.170055 0.173957 0.028 Uiso 1 1 calc R U . . .
C20 C 0.60389(18) 0.58493(13) 0.35851(8) 0.0298(3) Uani 1 1 d . . . . .
H20A H 0.699101 0.626282 0.348813 0.045 Uiso 1 1 calc R U . . .
H20B H 0.580959 0.601425 0.402336 0.045 Uiso 1 1 calc R U . . .
H20C H 0.529004 0.628901 0.332479 0.045 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 C5 1.3462(13) . ?
O1 C1 1.3665(12) . ?
O2 C2 1.3531(13) . ?
O2 H3 0.84(2) . ?
O3 C3 1.2613(13) . ?
O4 C13 1.2397(13) . ?
N1 C13 1.3420(13) . ?
N1 N2 1.4115(13) . ?
N1 H1 0.88(2) . ?
N2 C14 1.4163(15) . ?
N2 H2 0.87(2) . ?
C1 C2 1.3630(14) . ?
C1 C6 1.5191(14) . ?
C2 C3 1.4447(14) . ?
C3 C4 1.4301(15) . ?
C4 C5 1.3533(15) . ?
C4 H4 0.9500 . ?
C5 C20 1.4888(17) . ?
C6 C11 1.5428(15) . ?
C6 C12 1.5487(15) . ?
C6 C7 1.5516(15) . ?
C7 C8 1.5274(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5282(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5251(18) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5341(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.5108(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 C15 1.3927(16) . ?
C14 C19 1.4010(16) . ?
C15 C16 1.3933(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.3912(18) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 O1 C1 121.95(9) . . ?
C2 O2 H3 111.8(13) . . ?
C13 N1 N2 119.94(9) . . ?
C13 N1 H1 122.8(15) . . ?
N2 N1 H1 116.7(15) . . ?
N1 N2 C14 114.54(9) . . ?
N1 N2 H2 109.7(13) . . ?
C14 N2 H2 111.8(13) . . ?
C2 C1 O1 119.58(9) . . ?
C2 C1 C6 126.54(9) . . ?
O1 C1 C6 113.79(8) . . ?
O2 C2 C1 120.15(9) . . ?
O2 C2 C3 119.26(9) . . ?
C1 C2 C3 120.58(9) . . ?
O3 C3 C4 123.68(10) . . ?
O3 C3 C2 120.00(10) . . ?
C4 C3 C2 116.31(9) . . ?
C5 C4 C3 120.08(9) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C5 C4 121.41(10) . . ?
O1 C5 C20 112.06(10) . . ?
C4 C5 C20 126.53(10) . . ?
C1 C6 C11 112.06(8) . . ?
C1 C6 C12 108.15(8) . . ?
C11 C6 C12 109.37(8) . . ?
C1 C6 C7 111.47(8) . . ?
C11 C6 C7 108.11(8) . . ?
C12 C6 C7 107.58(8) . . ?
C8 C7 C6 113.10(9) . . ?
C8 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 111.42(10) . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C8 110.35(9) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 111.14(10) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C6 113.51(9) . . ?
C10 C11 H11A 108.9 . . ?
C6 C11 H11A 108.9 . . ?
C10 C11 H11B 108.9 . . ?
C6 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C6 113.56(9) . . ?
C13 C12 H12A 108.9 . . ?
C6 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C6 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O4 C13 N1 122.47(10) . . ?
O4 C13 C12 122.39(9) . . ?
N1 C13 C12 115.14(9) . . ?
C15 C14 C19 119.43(11) . . ?
C15 C14 N2 120.69(10) . . ?
C19 C14 N2 119.67(10) . . ?
C14 C15 C16 120.08(12) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C17 C16 C15 120.57(12) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.23(12) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C19 120.86(13) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C14 119.82(12) . . ?
C18 C19 H19 120.1 . . ?
C14 C19 H19 120.1 . . ?
C5 C20 H20A 109.5 . . ?
C5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 N1 N2 C14 107.03(12) . . . . ?
C5 O1 C1 C2 2.40(15) . . . . ?
C5 O1 C1 C6 -174.27(9) . . . . ?
O1 C1 C2 O2 -178.84(10) . . . . ?
C6 C1 C2 O2 -2.64(16) . . . . ?
O1 C1 C2 C3 0.03(15) . . . . ?
C6 C1 C2 C3 176.23(10) . . . . ?
O2 C2 C3 O3 -3.19(16) . . . . ?
C1 C2 C3 O3 177.93(10) . . . . ?
O2 C2 C3 C4 176.17(10) . . . . ?
C1 C2 C3 C4 -2.71(15) . . . . ?
O3 C3 C4 C5 -177.49(11) . . . . ?
C2 C3 C4 C5 3.17(15) . . . . ?
C1 O1 C5 C4 -1.94(16) . . . . ?
C1 O1 C5 C20 178.75(11) . . . . ?
C3 C4 C5 O1 -0.97(17) . . . . ?
C3 C4 C5 C20 178.23(13) . . . . ?
C2 C1 C6 C11 175.39(10) . . . . ?
O1 C1 C6 C11 -8.21(12) . . . . ?
C2 C1 C6 C12 -63.99(13) . . . . ?
O1 C1 C6 C12 112.40(10) . . . . ?
C2 C1 C6 C7 54.07(14) . . . . ?
O1 C1 C6 C7 -129.53(9) . . . . ?
C1 C6 C7 C8 69.97(11) . . . . ?
C11 C6 C7 C8 -53.62(11) . . . . ?
C12 C6 C7 C8 -171.63(9) . . . . ?
C6 C7 C8 C9 56.52(13) . . . . ?
C7 C8 C9 C10 -56.12(14) . . . . ?
C8 C9 C10 C11 55.68(13) . . . . ?
C9 C10 C11 C6 -56.31(12) . . . . ?
C1 C6 C11 C10 -69.65(11) . . . . ?
C12 C6 C11 C10 170.44(9) . . . . ?
C7 C6 C11 C10 53.58(11) . . . . ?
C1 C6 C12 C13 -62.63(11) . . . . ?
C11 C6 C12 C13 59.65(11) . . . . ?
C7 C6 C12 C13 176.84(8) . . . . ?
N2 N1 C13 O4 -1.65(17) . . . . ?
N2 N1 C13 C12 178.71(9) . . . . ?
C6 C12 C13 O4 53.05(14) . . . . ?
C6 C12 C13 N1 -127.31(10) . . . . ?
N1 N2 C14 C15 -132.17(11) . . . . ?
N1 N2 C14 C19 53.11(14) . . . . ?
C19 C14 C15 C16 -0.03(18) . . . . ?
N2 C14 C15 C16 -174.76(11) . . . . ?
C14 C15 C16 C17 0.51(19) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C15 C14 C19 C18 -0.5(2) . . . . ?
N2 C14 C19 C18 174.27(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88(2) 1.95(2) 2.8168(12) 167(2) 1_455 yes
N2 H2 O3 0.87(2) 2.07(2) 2.8834(13) 157.0(17) 3_655 yes

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_tet-acid
_database_code_depnum_ccdc_archive 'CCDC 2270313'
loop_
_audit_author_name
_audit_author_address
'Darina Ildarovna Nasyrova'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-10-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H22N2O5
_chemical_oxdiff_usercomment     TET-Acid
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.80840(10)
_cell_length_b                   14.35350(10)
_cell_length_c                   12.24630(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.4030(10)
_cell_angle_gamma                90
_cell_volume                     1635.92(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    29081
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5720
_cell_measurement_theta_min      3.0730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (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_density_diffrn    1.382
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41248
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.731
_diffrn_reflns_theta_min         4.751
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(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 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  84.00   0.45    0.30    --   48.57-108.00 -40.00  140
  2  ω    -82.00 -18.10   0.45    0.80    --  -86.25 108.00  56.00  142
  3  ω   -155.00 -83.00   0.45    0.80    --  -86.25-108.00 -40.00  160
  4  ω    104.00 176.00   0.45    0.80    --  107.75 108.00  56.00  160
  5  ω     39.00 106.05   0.45    0.80    --  107.75-108.00 -40.00  149
  6  ω   -118.00 -73.00   0.45    0.30    --  -48.57-125.00 120.00  100
  7  ω   -120.00 -27.75   0.45    0.30    --  -48.57 -77.00 -90.00  205
  8  ω    -82.00  -1.00   0.45    0.30    --  -48.57 108.00  56.00  180
  9  ω   -118.00 -73.00   0.45    0.30    --  -48.57-125.00  60.00  100
 10  ω   -118.00 -73.00   0.45    0.30    --  -48.57-125.00  90.00  100
 11  ω    -26.00  24.85   0.45    0.30    --  -48.57  19.00 150.00  113
 12  ω    -22.00  62.15   0.45    0.30    --   48.57 -57.00   0.00  187
 13  ω    -25.00  25.40   0.45    0.30    --   48.57 -19.00 -60.00  112
 14  ω     34.00  92.05   0.45    0.30    --   48.57-125.00  60.00  129
 15  ω    -51.00 -15.00   0.45    0.80    --  -86.25  45.00   0.00   80
 16  ω     36.00 104.40   0.45    0.80    --  107.75 -95.00 -90.00  152
 17  ω     97.00 178.00   0.45    0.80    --  107.75  45.00 120.00  180
 18  ω     36.00 104.40   0.45    0.80    --  107.75 -77.00  30.00  152
 19  ω     95.00 176.00   0.45    0.80    --  107.75 125.00 150.00  180
 20  ω     38.00 105.05   0.45    0.80    --  107.75 -98.00 -35.04  149
 21  ω     39.00 111.00   0.45    0.80    --  107.75-125.00 -90.00  160
 22  ω     36.00  70.20   0.45    0.80    --  107.75 -61.00 150.00   76
 23  ω     36.00 104.40   0.45    0.80    --  107.75 -77.00  90.00  152
 24  ω     95.00 176.00   0.45    0.80    --  107.75 125.00-120.00  180
 25  ω     39.00 106.05   0.45    0.80    --  107.75-106.00  64.29  149
 26  ω     39.00 111.00   0.45    0.80    --  107.75-125.00-180.00  160
 27  ω     97.00 178.00   0.45    0.80    --  107.75  45.00  60.00  180
 28  ω     39.00 111.00   0.45    0.80    --  107.75-125.00 -60.00  160
 29  ω     86.00 176.90   0.45    0.80    --  107.75  77.00-180.00  202
 30  ω     36.00 104.40   0.45    0.80    --  107.75 -95.00-150.00  152
 31  ω     97.00 178.00   0.45    0.80    --  107.75  45.00 -30.00  180
 32  ω     39.00 111.00   0.45    0.80    --  107.75-125.00 120.00  160
 33  ω     86.00 176.90   0.45    0.80    --  107.75  77.00-120.00  202
 34  ω     97.00 178.00   0.45    0.80    --  107.75  15.00 -60.00  180
 35  ω     36.00 104.40   0.45    0.80    --  107.75 -95.00  30.00  152
 36  ω     39.00 111.00   0.45    0.80    --  107.75-125.00-120.00  160
 37  ω     97.00 175.75   0.45    0.80    --  107.75 122.00 -63.41  175
 38  ω     95.00 176.00   0.45    0.80    --  107.75 125.00  90.00  180
 39  ω     39.00 106.05   0.45    0.80    --  107.75-108.00  11.04  149
 40  ω     36.00 104.40   0.45    0.80    --  107.75 -95.00 -30.00  152
 41  ω     95.00 176.00   0.45    0.80    --  107.75 125.00   0.00  180
 42  ω     51.00 109.05   0.45    0.80    --  107.75-125.00 -30.00  129
 43  ω    116.00 140.75   0.45    0.80    --  107.75  30.00-150.00   55
 44  ω    151.00 178.00   0.45    0.80    --  107.75  30.00-150.00   60
 45  ω     77.00 105.35   0.45    0.80    --  107.75 -99.00-127.76   63
 46  ω     36.00  70.20   0.45    0.80    --  107.75 -77.00  60.00   76
 47  ω     44.00  70.10   0.45    0.80    --  107.75 -95.00 120.00   58
 48  ω     41.00  67.10   0.45    0.80    --  107.75-125.00  30.00   58
 49  ω    127.00 158.05   0.45    0.80    --  107.75 125.00-150.00   69
 50  ω     36.00  62.10   0.45    0.80    --  107.75 -77.00 -60.00   58
 51  ω     54.00  80.10   0.45    0.80    --  107.75 -77.00 -30.00   58
 52  ω     43.00  69.10   0.45    0.80    --  107.75 -77.00   0.00   58
 53  ω     39.00  65.10   0.45    0.80    --  107.75-125.00   0.00   58
 54  ω    106.00 177.10   0.45    0.80    --  107.75  61.00 150.00  158
 55  ω     44.00  70.10   0.45    0.80    --  107.75 -95.00   0.00   58
 56  ω     43.00  69.10   0.45    0.80    --  107.75 -95.00  90.00   58
 57  ω     36.00  62.10   0.45    0.80    --  107.75 -94.00-153.03   58
 58  ω     78.00 104.10   0.45    0.80    --  107.75 -95.00  90.00   58
 59  ω     40.00 106.15   0.45    0.80    --  107.75-106.00 177.56  147
 60  ω    122.00 164.30   0.45    0.80    --  107.75 125.00 -30.00   94
 61  ω    134.00 159.65   0.45    0.80    --  107.75 125.00 120.00   57
 62  ω    123.00 147.75   0.45    0.80    --  107.75  30.00 -30.00   55
 63  ω    124.00 164.05   0.45    0.80    --  107.75  15.00-150.00   89
 64  ω    120.00 145.65   0.45    0.80    --  107.75  77.00  30.00   57
 65  ω     92.00 122.15   0.45    0.80    --  107.75 -87.00  65.56   67
 66  ω     37.00 107.20   0.45    0.80    --  107.75  -1.00 124.00  156
 67  ω    125.00 149.75   0.45    0.80    --  107.75  45.00 150.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0394849000
_diffrn_orient_matrix_UB_12      0.1034400000
_diffrn_orient_matrix_UB_13      0.0044170000
_diffrn_orient_matrix_UB_21      0.0114013000
_diffrn_orient_matrix_UB_22      0.0144607000
_diffrn_orient_matrix_UB_23      -0.1214929000
_diffrn_orient_matrix_UB_31      -0.1604055000
_diffrn_orient_matrix_UB_32      -0.0244532000
_diffrn_orient_matrix_UB_33      -0.0530212000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3382
_reflns_number_total             3480
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.061
_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)+(0.0433P)²+0.7451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.08754(9) 0.59587(6) 0.48344(7) 0.0271(2) Uani 1 1 d . . . . .
O2 O 0.56110(8) 0.35701(5) 0.74298(7) 0.02115(18) Uani 1 1 d . . . . .
O3 O 0.51975(10) 0.57493(6) 0.87059(8) 0.0270(2) Uani 1 1 d . . . . .
H3 H 0.433(2) 0.5913(15) 0.8131(19) 0.062(6) Uiso 1 1 d . . . . .
O4 O 0.74706(10) 0.28650(6) 0.87308(8) 0.0305(2) Uani 1 1 d . . . . .
N1 N 0.27854(10) 0.53164(7) 0.62185(8) 0.0191(2) Uani 1 1 d . . . . .
N2 N 0.27799(10) 0.59946(7) 0.70476(8) 0.0199(2) Uani 1 1 d . . . . .
H2 H 0.2669(17) 0.6567(12) 0.6701(14) 0.032(4) Uiso 1 1 d . . . . .
C1 C 0.17816(12) 0.53554(8) 0.51270(10) 0.0214(2) Uani 1 1 d . . . . .
C2 C 0.20950(13) 0.45525(9) 0.44596(10) 0.0243(2) Uani 1 1 d . . . . .
H2A H 0.245588 0.478145 0.383930 0.029 Uiso 1 1 calc R U . . .
H2B H 0.121284 0.418316 0.410747 0.029 Uiso 1 1 calc R U . . .
C3 C 0.32513(11) 0.39472(8) 0.53230(9) 0.0184(2) Uani 1 1 d . . . . .
C4 C 0.37334(11) 0.45652(8) 0.64024(9) 0.0178(2) Uani 1 1 d . . . . .
C5 C 0.25936(13) 0.30320(8) 0.55924(10) 0.0227(2) Uani 1 1 d . . . . .
H5A H 0.331746 0.270075 0.622273 0.027 Uiso 1 1 calc R U . . .
H5B H 0.176420 0.317990 0.585828 0.027 Uiso 1 1 calc R U . . .
C6 C 0.20954(14) 0.23932(9) 0.45340(11) 0.0278(3) Uani 1 1 d . . . . .
H6A H 0.176484 0.179309 0.475964 0.033 Uiso 1 1 calc R U . . .
H6B H 0.127101 0.268581 0.394693 0.033 Uiso 1 1 calc R U . . .
C7 C 0.32938(14) 0.22085(8) 0.40107(11) 0.0269(3) Uani 1 1 d . . . . .
H7A H 0.405963 0.183471 0.455494 0.032 Uiso 1 1 calc R U . . .
H7B H 0.290492 0.184406 0.329292 0.032 Uiso 1 1 calc R U . . .
C8 C 0.39311(13) 0.31180(8) 0.37458(10) 0.0226(2) Uani 1 1 d . . . . .
H8A H 0.318902 0.346634 0.314730 0.027 Uiso 1 1 calc R U . . .
H8B H 0.473385 0.297919 0.344388 0.027 Uiso 1 1 calc R U . . .
C9 C 0.44798(12) 0.37163(8) 0.48328(10) 0.0212(2) Uani 1 1 d . . . . .
H9A H 0.489289 0.430176 0.464736 0.025 Uiso 1 1 calc R U . . .
H9B H 0.524935 0.337741 0.541947 0.025 Uiso 1 1 calc R U . . .
C10 C 0.48537(12) 0.44076(7) 0.73643(9) 0.0183(2) Uani 1 1 d . . . . .
C11 C 0.55457(12) 0.49082(8) 0.84373(10) 0.0205(2) Uani 1 1 d . . . . .
C12 C 0.66375(12) 0.43803(8) 0.91016(10) 0.0231(2) Uani 1 1 d . . . . .
H12 H 0.726036 0.454055 0.984428 0.028 Uiso 1 1 calc R U . . .
C13 C 0.66893(12) 0.35415(8) 0.84916(10) 0.0227(2) Uani 1 1 d . . . . .
C14 C 0.16801(12) 0.58673(8) 0.75899(9) 0.0200(2) Uani 1 1 d . . . . .
C15 C 0.12928(13) 0.66512(9) 0.80944(10) 0.0245(2) Uani 1 1 d . . . . .
H15 H 0.170952 0.724021 0.804219 0.029 Uiso 1 1 calc R U . . .
C16 C 0.02897(14) 0.65619(9) 0.86754(11) 0.0278(3) Uani 1 1 d . . . . .
H16 H 0.001896 0.709246 0.902249 0.033 Uiso 1 1 calc R U . . .
C17 C -0.03168(13) 0.57023(10) 0.87500(10) 0.0278(3) Uani 1 1 d . . . . .
H17 H -0.101539 0.564668 0.913523 0.033 Uiso 1 1 calc R U . . .
C18 C 0.00959(13) 0.49215(9) 0.82621(10) 0.0253(3) Uani 1 1 d . . . . .
H18 H -0.031145 0.433128 0.832455 0.030 Uiso 1 1 calc R U . . .
C19 C 0.11052(12) 0.50001(8) 0.76812(10) 0.0224(2) Uani 1 1 d . . . . .
H19 H 0.139492 0.446618 0.735241 0.027 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 C1 1.2113(14) . ?
O2 C10 1.4019(13) . ?
O2 C13 1.3938(14) . ?
O3 H3 0.95(2) . ?
O3 C11 1.3241(14) . ?
O4 C13 1.2142(15) . ?
N1 N2 1.4078(13) . ?
N1 C1 1.3886(15) . ?
N1 C4 1.3949(14) . ?
N2 H2 0.916(17) . ?
N2 C14 1.4458(14) . ?
C1 C2 1.4997(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5499(16) . ?
C3 C4 1.5373(15) . ?
C3 C5 1.5443(15) . ?
C3 C9 1.5423(15) . ?
C4 C10 1.3524(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5360(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5291(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5259(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5319(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.4631(15) . ?
C11 C12 1.3538(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.4262(16) . ?
C14 C15 1.3929(16) . ?
C14 C19 1.3855(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3902(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.3852(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3891(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.3940(16) . ?
C19 H19 0.9500 . ?

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
C13 O2 C10 108.12(9) . . ?
C11 O3 H3 106.5(13) . . ?
C1 N1 N2 120.22(9) . . ?
C1 N1 C4 114.86(9) . . ?
C4 N1 N2 124.91(9) . . ?
N1 N2 H2 108.2(10) . . ?
N1 N2 C14 114.66(9) . . ?
C14 N2 H2 109.3(10) . . ?
O1 C1 N1 123.00(11) . . ?
O1 C1 C2 130.21(11) . . ?
N1 C1 C2 106.77(9) . . ?
C1 C2 H2A 110.3 . . ?
C1 C2 H2B 110.3 . . ?
C1 C2 C3 106.90(9) . . ?
H2A C2 H2B 108.6 . . ?
C3 C2 H2A 110.3 . . ?
C3 C2 H2B 110.3 . . ?
C4 C3 C2 102.90(9) . . ?
C4 C3 C5 110.06(9) . . ?
C4 C3 C9 113.12(9) . . ?
C5 C3 C2 110.95(9) . . ?
C9 C3 C2 110.38(9) . . ?
C9 C3 C5 109.31(9) . . ?
N1 C4 C3 107.39(9) . . ?
C10 C4 N1 125.93(10) . . ?
C10 C4 C3 126.67(10) . . ?
C3 C5 H5A 109.3 . . ?
C3 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C3 111.75(9) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 C5 112.04(10) . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C8 C7 C6 111.19(10) . . ?
C8 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C7 C8 C9 110.48(9) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C8 C9 C3 110.82(9) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
O2 C10 C11 106.41(9) . . ?
C4 C10 O2 117.61(10) . . ?
C4 C10 C11 135.98(10) . . ?
O3 C11 C10 126.02(10) . . ?
O3 C11 C12 125.32(11) . . ?
C12 C11 C10 108.63(10) . . ?
C11 C12 H12 126.0 . . ?
C11 C12 C13 108.06(10) . . ?
C13 C12 H12 126.0 . . ?
O2 C13 C12 108.77(10) . . ?
O4 C13 O2 118.94(11) . . ?
O4 C13 C12 132.29(11) . . ?
C15 C14 N2 116.69(10) . . ?
C19 C14 N2 122.16(10) . . ?
C19 C14 C15 120.99(10) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.26(12) . . ?
C16 C15 H15 120.4 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.26(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.04(11) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.30(12) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.12(11) . . ?
C14 C19 H19 120.4 . . ?
C18 C19 H19 120.4 . . ?

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
O3 H3 N1 0.95(2) 2.50(2) 3.2729(13) 138.2(17) . yes
O3 H3 N2 0.95(2) 1.68(2) 2.6136(13) 169(2) . yes
N2 H2 O4 0.916(17) 1.929(17) 2.8335(13) 168.9(15) 2_656 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 -173.18(12) . . . . ?
O2 C10 C11 O3 177.17(10) . . . . ?
O2 C10 C11 C12 -0.92(12) . . . . ?
O3 C11 C12 C13 -177.90(11) . . . . ?
N1 N2 C14 C15 -158.36(10) . . . . ?
N1 N2 C14 C19 26.13(15) . . . . ?
N1 C1 C2 C3 8.09(12) . . . . ?
N1 C4 C10 O2 174.49(9) . . . . ?
N1 C4 C10 C11 -5.5(2) . . . . ?
N2 N1 C1 O1 0.25(17) . . . . ?
N2 N1 C1 C2 179.10(9) . . . . ?
N2 N1 C4 C3 173.75(9) . . . . ?
N2 N1 C4 C10 -5.26(17) . . . . ?
N2 C14 C15 C16 -177.02(10) . . . . ?
N2 C14 C19 C18 177.04(10) . . . . ?
C1 N1 N2 C14 77.66(13) . . . . ?
C1 N1 C4 C3 -5.22(12) . . . . ?
C1 N1 C4 C10 175.77(10) . . . . ?
C1 C2 C3 C4 -10.63(11) . . . . ?
C1 C2 C3 C5 107.04(11) . . . . ?
C1 C2 C3 C9 -131.62(10) . . . . ?
C2 C3 C4 N1 9.61(11) . . . . ?
C2 C3 C4 C10 -171.39(11) . . . . ?
C2 C3 C5 C6 66.72(12) . . . . ?
C2 C3 C9 C8 -64.08(12) . . . . ?
C3 C4 C10 O2 -4.33(16) . . . . ?
C3 C4 C10 C11 175.69(11) . . . . ?
C3 C5 C6 C7 53.73(14) . . . . ?
C4 N1 N2 C14 -101.26(12) . . . . ?
C4 N1 C1 O1 179.28(10) . . . . ?
C4 N1 C1 C2 -1.88(13) . . . . ?
C4 C3 C5 C6 179.95(10) . . . . ?
C4 C3 C9 C8 -178.76(9) . . . . ?
C4 C10 C11 O3 -2.9(2) . . . . ?
C4 C10 C11 C12 179.05(13) . . . . ?
C5 C3 C4 N1 -108.69(10) . . . . ?
C5 C3 C4 C10 70.31(14) . . . . ?
C5 C3 C9 C8 58.22(12) . . . . ?
C5 C6 C7 C8 -53.88(14) . . . . ?
C6 C7 C8 C9 56.49(13) . . . . ?
C7 C8 C9 C3 -59.37(13) . . . . ?
C9 C3 C4 N1 128.71(10) . . . . ?
C9 C3 C4 C10 -52.29(15) . . . . ?
C9 C3 C5 C6 -55.24(12) . . . . ?
C10 O2 C13 O4 179.35(10) . . . . ?
C10 O2 C13 C12 -1.18(12) . . . . ?
C10 C11 C12 C13 0.21(13) . . . . ?
C11 C12 C13 O2 0.60(13) . . . . ?
C11 C12 C13 O4 179.97(13) . . . . ?
C13 O2 C10 C4 -178.71(10) . . . . ?
C13 O2 C10 C11 1.28(11) . . . . ?
C14 C15 C16 C17 -0.02(18) . . . . ?
C15 C14 C19 C18 1.72(17) . . . . ?
C15 C16 C17 C18 1.20(19) . . . . ?
C16 C17 C18 C19 -0.92(18) . . . . ?
C17 C18 C19 C14 -0.52(18) . . . . ?
C19 C14 C15 C16 -1.46(18) . . . . ?

_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 1.438
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_kjoket5m
_database_code_depnum_ccdc_archive 'CCDC 2270309'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Science
Russia
;
_audit_update_record             
;
2023-06-15 deposited with the CCDC.	2023-08-22 downloaded from the CCDC.
;
_audit_creation_date             2022-11-30
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N4 O6, C7 H8'
_chemical_formula_sum            'C30 H32 N4 O6'
_chemical_formula_weight         544.59
_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                   19.3210(2)
_cell_length_b                   7.16745(8)
_cell_length_c                   20.9490(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.0334(14)
_cell_angle_gamma                90
_cell_volume                     2725.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15608
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      77.3470
_cell_measurement_theta_min      3.8160
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66569
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.72a (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    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            33634
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.833
_diffrn_reflns_theta_min         2.687
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -46.00  23.00   0.50    5.50    --  -48.67  41.00-132.00  138
  2  ω   -120.00 -38.00   0.50    5.50    --  -48.67 -41.00  74.00  164
  3  ω     11.00  36.00   0.50    5.50    --   48.67 -41.00  74.00   50
  4  ω     52.00  80.00   0.50    5.50    --   48.67  41.00-132.00   56
  5  ω    -46.00 -21.00   0.50   22.00    --  -86.25  41.00-132.00   50
  6  ω   -126.00 -90.00   0.50   22.00    --  -86.25 -41.00  74.00   72
  7  ω     99.00 142.00   0.50   22.00    --  107.75  41.00-132.00   86
  8  ω    -14.00  26.00   0.50    5.50    --  -48.67  19.00   0.00   80
  9  ω   -105.00 -74.00   0.50    5.50    --  -48.67-125.00-150.00   62
 10  ω    -21.00  25.00   0.50    5.50    --   48.67 -19.00 -30.00   92
 11  ω    -44.00 -19.00   0.50   22.00    --  -86.25  45.00  60.00   50
 12  ω    120.00 163.00   0.50   22.00    --  107.75  15.00 -30.00   86
 13  ω     38.00  63.00   0.50   22.00    --  107.75 -77.00-120.00   50
 14  ω     39.00  64.00   0.50   22.00    --  107.75 -61.00 -30.00   50
 15  ω    126.00 156.00   0.50   22.00    --  107.75  30.00-180.00   60
 16  ω     40.00  71.00   0.50   22.00    --  107.75 -61.00-180.00   62
 17  ω     47.00  73.00   0.50   22.00    --  107.75-125.00   0.00   52
 18  ω    110.00 137.00   0.50   22.00    --  107.75  45.00-120.00   54
 19  ω    144.00 175.00   0.50   22.00    --  107.75  45.00-120.00   62
 20  ω     39.00  98.00   0.50   22.00    --  107.75 -98.00  35.98  118
 21  ω     40.00 105.00   0.50   22.00    --  107.75 -77.00 120.00  130
 22  ω    117.00 143.00   0.50   22.00    --  107.75 107.00-170.22   52
 23  ω     97.00 125.00   0.50   22.00    --  107.75  30.00   0.00   56
 24  ω     91.00 127.00   0.50   22.00    --  107.75  77.00  30.00   72
 25  ω    133.00 159.00   0.50   22.00    --  107.75  30.00   0.00   52
 26  ω     41.00 102.00   0.50   22.00    --  107.75 -95.00 120.00  122
 27  ω     57.00 105.00   0.50   22.00    --  107.75-103.00  84.50   96
 28  ω    101.00 127.00   0.50   22.00    --  107.75  61.00-150.00   52
 29  ω    139.00 165.00   0.50   22.00    --  107.75  61.00-150.00   52
 30  ω     54.00  80.00   0.50   22.00    --  107.75-125.00 120.00   52
 31  ω     68.00 104.00   0.50   22.00    --  107.75-125.00 -90.00   72
 32  ω    146.00 171.00   0.50   22.00    --  107.75  61.00-180.00   50
 33  ω     36.00  61.00   0.50   22.00    --  107.75 -61.00 120.00   50
 34  ω     42.00  72.00   0.50   22.00    --  107.75-125.00  30.00   60
 35  ω     82.00 107.00   0.50   22.00    --  107.75-125.00  30.00   50
 36  ω    103.00 132.00   0.50   22.00    --  107.75  30.00  60.00   58
 37  ω    142.00 168.00   0.50   22.00    --  107.75  30.00  60.00   52
 38  ω     93.00 119.00   0.50   22.00    --  107.75  61.00-180.00   52
 39  ω     67.00 114.00   0.50   22.00    --  107.75-143.00 -28.98   94
 40  ω     69.00  98.00   0.50   22.00    --  107.75 -77.00-120.00   58
 41  ω    138.00 164.00   0.50   22.00    --  107.75  77.00  30.00   52
 42  ω     95.00 134.00   0.50   22.00    --  107.75  61.00 150.00   78
 43  ω     98.00 136.00   0.50   22.00    --  107.75  15.00   0.00   76
 44  ω    145.00 178.00   0.50   22.00    --  107.75  15.00   0.00   66
 45  ω     39.00  94.00   0.50   22.00    --  107.75 -77.00 -60.00  110
 46  ω     37.00  62.00   0.50   22.00    --  107.75 -77.00  90.00   50
 47  ω     37.00  62.00   0.50   22.00    --  107.75 -77.00   0.00   50
 48  ω     78.00 104.00   0.50   22.00    --  107.75 -77.00   0.00   52
 49  ω     49.00  74.00   0.50   22.00    --  107.75 -95.00-180.00   50
 50  ω     40.00  80.00   0.50   22.00    --  107.75 -95.00 150.00   80
 51  ω    115.00 141.00   0.50   22.00    --  107.75 122.00-133.21   52
 52  ω    117.00 143.00   0.50   22.00    --  107.75  45.00-150.00   52
 53  ω    135.00 178.00   0.50   22.00    --  107.75  30.00 -90.00   86
 54  ω    139.00 175.00   0.50   22.00    --  107.75 125.00   0.00   72
 55  ω     95.00 121.00   0.50   22.00    --  107.75 -88.00 -74.45   52
 56  ω     37.00  68.00   0.50   22.00    --  107.75 -61.00 -60.00   62
;
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4980
_reflns_number_total             5757
_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 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.72a (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  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.416
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.054
_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)+(0.0513P)²+1.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1108
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C9(H9), C10(H10), C19(H19), C20(H20), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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 0.48301(5) 0.21431(13) 0.19493(4) 0.0185(2) Uani 1 1 d . . . . .
O2 O 0.59311(5) 0.09422(14) 0.39339(5) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.46233(5) 0.27018(13) 0.36063(4) 0.0183(2) Uani 1 1 d . . . . .
O4 O 0.43486(6) 0.00512(14) 0.40669(5) 0.0263(2) Uani 1 1 d . . . . .
O5 O 0.44495(6) 0.78263(14) 0.23266(5) 0.0263(2) Uani 1 1 d . . . . .
O6 O 0.21984(5) 0.16896(15) 0.16779(5) 0.0255(2) Uani 1 1 d . . . . .
N1 N 0.48057(6) 0.47961(15) 0.26166(5) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.55144(6) 0.51196(16) 0.30753(6) 0.0181(2) Uani 1 1 d . . . . .
H2 H 0.5530(10) 0.558(3) 0.3466(10) 0.032(5) Uiso 1 1 d . . . . .
N3 N 0.42519(6) 0.29466(17) 0.45013(5) 0.0200(2) Uani 1 1 d . . . . .
N4 N 0.40950(7) 0.3851(2) 0.54518(6) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.45425(7) 0.29198(18) 0.24485(6) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.47771(7) 0.16721(18) 0.30819(6) 0.0170(3) Uani 1 1 d . . . . .
H2A H 0.447520 0.050516 0.298290 0.020 Uiso 1 1 calc R U . . .
C3 C 0.55964(7) 0.11557(19) 0.33256(7) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.58888(7) 0.08289(19) 0.27907(7) 0.0216(3) Uani 1 1 d . . . . .
H4 H 0.636448 0.029336 0.289462 0.026 Uiso 1 1 calc R U . . .
C5 C 0.54959(7) 0.12733(19) 0.21452(7) 0.0197(3) Uani 1 1 d . . . . .
C6 C 0.57151(8) 0.0864(2) 0.15445(7) 0.0259(3) Uani 1 1 d . . . . .
H6A H 0.536285 -0.001232 0.124398 0.039 Uiso 1 1 calc R U . . .
H6B H 0.620876 0.031014 0.169606 0.039 Uiso 1 1 calc R U . . .
H6C H 0.571824 0.202387 0.129790 0.039 Uiso 1 1 calc R U . . .
C7 C 0.44113(7) 0.1713(2) 0.40478(6) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.42038(8) 0.2415(2) 0.51167(7) 0.0252(3) Uani 1 1 d . . . . .
H8 H 0.424456 0.116475 0.527592 0.030 Uiso 1 1 calc R U . . .
C9 C 0.40648(7) 0.5397(2) 0.50406(7) 0.0250(3) Uani 1 1 d . . . . .
H9 H 0.398248 0.664167 0.515275 0.030 Uiso 1 1 calc R U . . .
C10 C 0.41689(7) 0.4879(2) 0.44599(7) 0.0217(3) Uani 1 1 d . . . . .
H10 H 0.418260 0.566611 0.409953 0.026 Uiso 1 1 calc R U . . .
C11 C 0.43324(7) 0.61614(19) 0.22583(7) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.36707(7) 0.51689(19) 0.17732(7) 0.0203(3) Uani 1 1 d . . . . .
H12A H 0.369991 0.512831 0.131078 0.024 Uiso 1 1 calc R U . . .
H12B H 0.320937 0.580949 0.175207 0.024 Uiso 1 1 calc R U . . .
C13 C 0.36966(7) 0.31845(18) 0.20628(6) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.32469(7) 0.3119(2) 0.25441(7) 0.0203(3) Uani 1 1 d . . . . .
H14A H 0.336382 0.195707 0.281543 0.024 Uiso 1 1 calc R U . . .
H14B H 0.338630 0.418849 0.286196 0.024 Uiso 1 1 calc R U . . .
C15 C 0.24216(7) 0.3193(2) 0.21473(7) 0.0240(3) Uani 1 1 d . . . . .
H15A H 0.214692 0.313522 0.246835 0.029 Uiso 1 1 calc R U . . .
H15B H 0.230021 0.439099 0.189838 0.029 Uiso 1 1 calc R U . . .
C16 C 0.25573(7) 0.1829(2) 0.11887(7) 0.0246(3) Uani 1 1 d . . . . .
H16A H 0.242972 0.303863 0.094886 0.029 Uiso 1 1 calc R U . . .
H16B H 0.237641 0.082287 0.084819 0.029 Uiso 1 1 calc R U . . .
C17 C 0.33903(7) 0.16810(19) 0.15120(7) 0.0206(3) Uani 1 1 d . . . . .
H17A H 0.361764 0.182837 0.115719 0.025 Uiso 1 1 calc R U . . .
H17B H 0.352213 0.042933 0.171762 0.025 Uiso 1 1 calc R U . . .
C18 C 0.60578(7) 0.57722(18) 0.28291(6) 0.0182(3) Uani 1 1 d . . . . .
C19 C 0.59856(8) 0.5731(2) 0.21435(7) 0.0213(3) Uani 1 1 d . . . . .
H19 H 0.554307 0.528809 0.181491 0.026 Uiso 1 1 calc R U . . .
C20 C 0.65624(8) 0.6339(2) 0.19422(7) 0.0249(3) Uani 1 1 d . . . . .
H20 H 0.651249 0.629221 0.147529 0.030 Uiso 1 1 calc R U . . .
C21 C 0.72111(8) 0.7015(2) 0.24135(8) 0.0258(3) Uani 1 1 d . . . . .
H21 H 0.759952 0.745128 0.227136 0.031 Uiso 1 1 calc R U . . .
C22 C 0.72812(7) 0.7042(2) 0.30965(7) 0.0239(3) Uani 1 1 d . . . . .
H22 H 0.772310 0.749404 0.342355 0.029 Uiso 1 1 calc R U . . .
C23 C 0.67153(7) 0.6418(2) 0.33059(7) 0.0211(3) Uani 1 1 d . . . . .
H23 H 0.677365 0.642949 0.377495 0.025 Uiso 1 1 calc R U . . .
C24 C 0.27053(9) 0.5676(3) -0.01950(8) 0.0349(4) Uani 1 1 d . . . . .
H24 H 0.218425 0.555081 -0.036218 0.042 Uiso 1 1 calc R U . . .
C25 C 0.30166(11) 0.7372(3) 0.00741(9) 0.0403(4) Uani 1 1 d . . . . .
H25 H 0.270841 0.838556 0.009501 0.048 Uiso 1 1 calc R U . . .
C26 C 0.37734(11) 0.7593(3) 0.03120(9) 0.0435(4) Uani 1 1 d . . . . .
H26 H 0.398722 0.875761 0.049110 0.052 Uiso 1 1 calc R U . . .
C27 C 0.42146(10) 0.6099(3) 0.02860(9) 0.0460(5) Uani 1 1 d . . . . .
H27 H 0.473495 0.624130 0.044855 0.055 Uiso 1 1 calc R U . . .
C28 C 0.39071(10) 0.4399(3) 0.00259(9) 0.0392(4) Uani 1 1 d . . . . .
H28 H 0.421784 0.338000 0.001640 0.047 Uiso 1 1 calc R U . . .
C29 C 0.31363(9) 0.4167(2) -0.02250(8) 0.0333(4) Uani 1 1 d . . . . .
C30 C 0.27834(11) 0.2360(3) -0.05214(9) 0.0415(4) Uani 1 1 d . . . . .
H30A H 0.248607 0.189430 -0.025883 0.062 Uiso 1 1 calc R U . . .
H30B H 0.316619 0.144565 -0.050516 0.062 Uiso 1 1 calc R U . . .
H30C H 0.246671 0.255592 -0.099436 0.062 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 C1 1.4528(15) . ?
O1 C5 1.3601(16) . ?
O2 C3 1.2252(17) . ?
O3 C2 1.4364(15) . ?
O3 C7 1.3362(16) . ?
O4 C7 1.1994(18) . ?
O5 C11 1.2139(17) . ?
O6 C15 1.4227(17) . ?
O6 C16 1.4240(18) . ?
N1 N2 1.3967(14) . ?
N1 C1 1.4382(16) . ?
N1 C11 1.3736(17) . ?
N2 H2 0.87(2) . ?
N2 C18 1.3994(17) . ?
N3 C7 1.4069(18) . ?
N3 C8 1.3777(18) . ?
N3 C10 1.3936(19) . ?
N4 C8 1.303(2) . ?
N4 C9 1.392(2) . ?
C1 C2 1.5342(17) . ?
C1 C13 1.5668(17) . ?
C2 H2A 1.0000 . ?
C2 C3 1.5328(18) . ?
C3 C4 1.436(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3429(19) . ?
C5 C6 1.4880(19) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.351(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.5109(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5404(18) . ?
C13 C14 1.5408(18) . ?
C13 C17 1.5412(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5260(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5210(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.3948(18) . ?
C18 C23 1.3988(18) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C24 C25 1.387(3) . ?
C24 C29 1.379(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.381(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.383(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.409(2) . ?
C29 C30 1.496(3) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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 O1 C1 120.93(10) . . ?
C7 O3 C2 116.73(10) . . ?
C15 O6 C16 109.72(11) . . ?
N2 N1 C1 120.31(10) . . ?
C11 N1 N2 124.75(11) . . ?
C11 N1 C1 114.77(10) . . ?
N1 N2 H2 114.7(13) . . ?
N1 N2 C18 118.97(10) . . ?
C18 N2 H2 115.3(13) . . ?
C8 N3 C7 123.97(12) . . ?
C8 N3 C10 106.85(12) . . ?
C10 N3 C7 129.02(12) . . ?
C8 N4 C9 105.99(12) . . ?
O1 C1 C2 109.07(10) . . ?
O1 C1 C13 105.30(9) . . ?
N1 C1 O1 110.13(10) . . ?
N1 C1 C2 111.00(10) . . ?
N1 C1 C13 103.41(10) . . ?
C2 C1 C13 117.61(10) . . ?
O3 C2 C1 106.54(10) . . ?
O3 C2 H2A 109.2 . . ?
O3 C2 C3 109.27(10) . . ?
C1 C2 H2A 109.2 . . ?
C3 C2 C1 113.22(11) . . ?
C3 C2 H2A 109.2 . . ?
O2 C3 C2 119.56(12) . . ?
O2 C3 C4 125.63(13) . . ?
C4 C3 C2 114.63(11) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.61(12) . . ?
C5 C4 H4 119.7 . . ?
O1 C5 C6 110.43(11) . . ?
C4 C5 O1 124.23(12) . . ?
C4 C5 C6 125.33(13) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 N3 108.92(11) . . ?
O4 C7 O3 127.45(13) . . ?
O4 C7 N3 123.62(13) . . ?
N3 C8 H8 124.4 . . ?
N4 C8 N3 111.16(13) . . ?
N4 C8 H8 124.4 . . ?
N4 C9 H9 124.7 . . ?
C10 C9 N4 110.55(13) . . ?
C10 C9 H9 124.7 . . ?
N3 C10 H10 127.3 . . ?
C9 C10 N3 105.44(13) . . ?
C9 C10 H10 127.3 . . ?
O5 C11 N1 125.00(12) . . ?
O5 C11 C12 128.51(12) . . ?
N1 C11 C12 106.48(11) . . ?
C11 C12 H12A 110.7 . . ?
C11 C12 H12B 110.7 . . ?
C11 C12 C13 105.30(10) . . ?
H12A C12 H12B 108.8 . . ?
C13 C12 H12A 110.7 . . ?
C13 C12 H12B 110.7 . . ?
C12 C13 C1 101.67(10) . . ?
C12 C13 C14 109.64(11) . . ?
C12 C13 C17 113.48(11) . . ?
C14 C13 C1 112.41(10) . . ?
C14 C13 C17 108.11(11) . . ?
C17 C13 C1 111.51(10) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 C13 111.15(11) . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
O6 C15 C14 111.28(11) . . ?
O6 C15 H15A 109.4 . . ?
O6 C15 H15B 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
O6 C16 H16A 109.2 . . ?
O6 C16 H16B 109.2 . . ?
O6 C16 C17 112.12(11) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C13 C17 H17A 109.4 . . ?
C13 C17 H17B 109.4 . . ?
C16 C17 C13 111.16(11) . . ?
C16 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 N2 123.33(12) . . ?
C19 C18 C23 119.23(12) . . ?
C23 C18 N2 117.38(12) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 C18 119.87(13) . . ?
C20 C19 H19 120.1 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.02(13) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.6 . . ?
C20 C21 C22 118.81(13) . . ?
C22 C21 H21 120.6 . . ?
C21 C22 H22 119.6 . . ?
C23 C22 C21 120.83(13) . . ?
C23 C22 H22 119.6 . . ?
C18 C23 H23 119.9 . . ?
C22 C23 C18 120.22(13) . . ?
C22 C23 H23 119.9 . . ?
C25 C24 H24 119.3 . . ?
C29 C24 H24 119.3 . . ?
C29 C24 C25 121.39(16) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.30(18) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 120.4 . . ?
C27 C26 C25 119.20(18) . . ?
C27 C26 H26 120.4 . . ?
C26 C27 H27 119.6 . . ?
C26 C27 C28 120.71(17) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.8 . . ?
C27 C28 C29 120.48(18) . . ?
C29 C28 H28 119.8 . . ?
C24 C29 C28 117.92(16) . . ?
C24 C29 C30 120.08(16) . . ?
C28 C29 C30 122.00(17) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O3 167.55(9) . . . . ?
O1 C1 C2 C3 47.43(14) . . . . ?
O1 C1 C13 C12 -89.14(11) . . . . ?
O1 C1 C13 C14 153.70(10) . . . . ?
O1 C1 C13 C17 32.10(14) . . . . ?
O2 C3 C4 C5 -173.76(14) . . . . ?
O3 C2 C3 O2 28.68(17) . . . . ?
O3 C2 C3 C4 -155.77(11) . . . . ?
O5 C11 C12 C13 -161.88(14) . . . . ?
O6 C16 C17 C13 -57.12(15) . . . . ?
N1 N2 C18 C19 -14.79(19) . . . . ?
N1 N2 C18 C23 168.04(12) . . . . ?
N1 C1 C2 O3 46.04(13) . . . . ?
N1 C1 C2 C3 -74.09(13) . . . . ?
N1 C1 C13 C12 26.46(12) . . . . ?
N1 C1 C13 C14 -90.70(12) . . . . ?
N1 C1 C13 C17 147.70(11) . . . . ?
N1 C11 C12 C13 19.18(14) . . . . ?
N2 N1 C1 O1 -79.95(13) . . . . ?
N2 N1 C1 C2 40.94(15) . . . . ?
N2 N1 C1 C13 167.95(10) . . . . ?
N2 N1 C11 O5 -5.1(2) . . . . ?
N2 N1 C11 C12 173.90(11) . . . . ?
N2 C18 C19 C20 -177.50(13) . . . . ?
N2 C18 C23 C22 178.50(13) . . . . ?
N4 C9 C10 N3 1.21(15) . . . . ?
C1 O1 C5 C4 9.56(19) . . . . ?
C1 O1 C5 C6 -171.40(11) . . . . ?
C1 N1 N2 C18 107.32(14) . . . . ?
C1 N1 C11 O5 179.63(13) . . . . ?
C1 N1 C11 C12 -1.38(15) . . . . ?
C1 C2 C3 O2 147.24(12) . . . . ?
C1 C2 C3 C4 -37.21(16) . . . . ?
C1 C13 C14 C15 -174.55(11) . . . . ?
C1 C13 C17 C16 174.32(11) . . . . ?
C2 O3 C7 O4 1.73(19) . . . . ?
C2 O3 C7 N3 -177.23(10) . . . . ?
C2 C1 C13 C12 149.17(11) . . . . ?
C2 C1 C13 C14 32.01(15) . . . . ?
C2 C1 C13 C17 -89.58(13) . . . . ?
C2 C3 C4 C5 11.00(19) . . . . ?
C3 C4 C5 O1 4.0(2) . . . . ?
C3 C4 C5 C6 -174.89(13) . . . . ?
C5 O1 C1 N1 87.11(13) . . . . ?
C5 O1 C1 C2 -34.94(15) . . . . ?
C5 O1 C1 C13 -162.02(11) . . . . ?
C7 O3 C2 C1 146.02(10) . . . . ?
C7 O3 C2 C3 -91.33(12) . . . . ?
C7 N3 C8 N4 176.08(12) . . . . ?
C7 N3 C10 C9 -176.40(12) . . . . ?
C8 N3 C7 O3 -162.53(12) . . . . ?
C8 N3 C7 O4 18.5(2) . . . . ?
C8 N3 C10 C9 -0.94(14) . . . . ?
C8 N4 C9 C10 -1.03(16) . . . . ?
C9 N4 C8 N3 0.40(16) . . . . ?
C10 N3 C7 O3 12.23(18) . . . . ?
C10 N3 C7 O4 -166.77(13) . . . . ?
C10 N3 C8 N4 0.34(16) . . . . ?
C11 N1 N2 C18 -67.72(17) . . . . ?
C11 N1 C1 O1 95.57(12) . . . . ?
C11 N1 C1 C2 -143.54(11) . . . . ?
C11 N1 C1 C13 -16.54(14) . . . . ?
C11 C12 C13 C1 -27.74(13) . . . . ?
C11 C12 C13 C14 91.41(12) . . . . ?
C11 C12 C13 C17 -147.60(11) . . . . ?
C12 C13 C14 C15 73.14(14) . . . . ?
C12 C13 C17 C16 -71.58(15) . . . . ?
C13 C1 C2 O3 -72.72(13) . . . . ?
C13 C1 C2 C3 167.15(11) . . . . ?
C13 C14 C15 O6 58.42(15) . . . . ?
C14 C13 C17 C16 50.26(14) . . . . ?
C15 O6 C16 C17 62.27(15) . . . . ?
C16 O6 C15 C14 -62.61(14) . . . . ?
C17 C13 C14 C15 -51.04(14) . . . . ?
C18 C19 C20 C21 -0.8(2) . . . . ?
C19 C18 C23 C22 1.2(2) . . . . ?
C19 C20 C21 C22 1.2(2) . . . . ?
C20 C21 C22 C23 -0.4(2) . . . . ?
C21 C22 C23 C18 -0.8(2) . . . . ?
C23 C18 C19 C20 -0.4(2) . . . . ?
C24 C25 C26 C27 -0.8(3) . . . . ?
C25 C24 C29 C28 -0.1(2) . . . . ?
C25 C24 C29 C30 -179.71(15) . . . . ?
C25 C26 C27 C28 0.0(3) . . . . ?
C26 C27 C28 C29 0.8(3) . . . . ?
C27 C28 C29 C24 -0.7(2) . . . . ?
C27 C28 C29 C30 178.89(16) . . . . ?
C29 C24 C25 C26 0.9(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
;
