# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

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

data_smi4
_database_code_depnum_ccdc_archive 'CCDC 1939718'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2019-07-10 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H11 N O3'
_chemical_formula_sum            'C16 H11 N O3'
_chemical_formula_weight         265.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'N O3 C16'
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                   5.6374(2)
_cell_length_b                   26.9520(7)
_cell_length_c                   8.3501(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.991(4)
_cell_angle_gamma                90
_cell_volume                     1213.33(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6343
_cell_measurement_temperature    100(3)
_cell_measurement_theta_max      71.9030
_cell_measurement_theta_min      3.2100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13070
_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         71.770
_diffrn_reflns_theta_min         3.279
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix3000
_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    -16.00  19.00   0.50    0.20    --   41.22 -94.00 -52.00   70
  2  ω     26.00  65.00   0.50    0.20    --   41.22 -94.00 -52.00   78
  3  ω     35.00  61.00   0.50    0.27    --  101.00 -94.00 -52.00   52
  4  ω     85.00 112.00   0.50    0.27    --  101.00  94.00  58.00   54
  5  ω    -49.00 -23.00   0.50    0.20    --  -41.22  94.00  58.00   52
  6  ω      0.00  25.00   0.50    0.20    --  -41.22  94.00  58.00   50
  7  ω   -101.00 -45.00   0.50    0.20    --  -41.22 -54.00-150.00  112
  8  ω    -21.00  54.00   0.50    0.20    --   41.22 -54.00 -60.00  150
  9  ω     45.00  81.00   0.50    0.20    --   41.22  54.00  30.00   72
 10  ω      6.00  43.00   0.50    0.20    --   41.22 -43.00   0.00   74
 11  ω     66.00  95.00   0.50    0.20    --   41.22  54.00  60.00   58
 12  ω    -21.00  31.00   0.50    0.20    --   41.22 -54.00-180.00  104
 13  ω     29.00  63.00   0.50    0.20    --   41.22  54.00  60.00   68
 14  ω     56.00  92.00   0.50    0.20    --   41.22  43.00 -90.00   72
 15  ω     42.00 119.00   0.50    0.27    --  101.00-133.00 120.00  154
 16  ω     93.00 132.00   0.50    0.27    --  101.00  59.00-120.00   78
 17  ω    103.00 147.00   0.50    0.27    --  101.00  33.00  30.00   88
 18  ω     86.00 152.00   0.50    0.27    --  101.00  50.00-180.00  132
 19  ω     86.00 132.00   0.50    0.27    --  101.00  50.00 150.00   92
 20  ω     97.00 123.00   0.50    0.27    --  101.00  33.00-150.00   52
 21  ω     35.00 110.00   0.50    0.27    --  101.00 -87.00 -90.00  150
 22  ω     53.00 117.00   0.50    0.27    --  101.00 -50.00 -90.00  128
 23  ω     93.00 120.00   0.50    0.27    --  101.00  33.00  60.00   54
 24  ω     31.00 114.00   0.50    0.27    --  101.00 -17.00-120.00  166
 25  ω     85.00 111.00   0.50    0.27    --  101.00 -42.00 -60.00   52
 26  ω     88.00 113.00   0.50    0.27    --  101.00  68.00  60.00   50
 27  ω    126.00 156.00   0.50    0.27    --  101.00  68.00  60.00   60
 28  ω    132.00 157.00   0.50    0.27    --  101.00  33.00 -30.00   50
 29  ω     41.00  67.00   0.50    0.27    --  101.00 -42.00 -60.00   52
 30  ω    114.00 156.00   0.50    0.27    --  101.00  77.00  30.00   84
 31  ω     46.00  71.00   0.50    0.27    --  101.00 -94.00 -52.00   50
 32  ω    -77.00 -41.00   0.50    0.20    --  -41.22 -32.00-120.00   72
 33  ω    -99.00 -73.00   0.50    0.20    --  -41.22 -54.00 -60.00   52
 34  ω    -63.00 -27.00   0.50    0.20    --  -41.22 -54.00 -60.00   72
 35  ω     77.00 104.00   0.50    0.20    --   41.22  32.00  30.00   54
 36  ω     48.00  97.00   0.50    0.20    --   41.22  65.00   0.00   98
 37  ω    -15.00  25.00   0.50    0.20    --   41.22 -43.00 -30.00   80
 38  ω      6.00  48.00   0.50    0.20    --   41.22 -21.00 -60.00   84
 39  ω     75.00 101.00   0.50    0.27    --  101.00 -25.00-150.00   52
 40  ω     39.00  68.00   0.50    0.27    --  101.00 -25.00-150.00   58
 41  ω     33.00 105.00   0.50    0.27    --  101.00 -17.00 -30.00  144
 42  ω    129.00 155.00   0.50    0.27    --  101.00  33.00 150.00   52
 43  ω     66.00 110.00   0.50    0.27    --  101.00 -33.00  30.00   88
 44  ω     78.00 104.00   0.50    0.27    --  101.00  77.00 150.00   52
 45  ω    127.00 153.00   0.50    0.27    --  101.00  77.00 150.00   52
 46  ω    121.00 156.00   0.50    0.27    --  101.00  33.00   0.00   70
 47  ω     41.00  78.00   0.50    0.27    --  101.00-133.00-150.00   74
 48  ω     42.00  90.00   0.50    0.27    --  101.00 -77.00   0.00   96
 49  ω     67.00  98.00   0.50    0.27    --  101.00 -59.00-120.00   62
 50  ω    100.00 129.00   0.50    0.27    --  101.00  50.00 -90.00   58
 51  ω     85.00 111.00   0.50    0.27    --  101.00 -42.00 -30.00   52
 52  ω    126.00 153.00   0.50    0.27    --  101.00  33.00-120.00   54
 53  ω     36.00 100.00   0.50    0.27    --  101.00 -87.00  90.00  128
 54  ω     94.00 120.00   0.50    0.27    --  101.00  33.00-120.00   52
 55  ω     35.00 103.00   0.50    0.27    --  101.00-111.00 -90.00  136
 56  ω     40.00  98.00   0.50    0.27    --  101.00 -42.00 120.00  116
 57  ω     57.00  83.00   0.50    0.27    --  101.00-133.00-120.00   52
 58  ω     98.00 123.00   0.50    0.27    --  101.00-133.00-120.00   50
 59  ω    132.00 157.00   0.50    0.27    --  101.00  33.00  60.00   50
 60  ω     84.00 126.00   0.50    0.27    --  101.00 -87.00 120.00   84
 61  ω    -65.00 -39.00   0.50    0.20    --  -41.22  95.00  57.00   52
 62  ω    -37.00  -2.00   0.50    0.20    --  -41.22  32.00-150.00   70
 63  ω    -18.00   8.00   0.50    0.20    --  -41.22  95.00  57.00   52
 64  ω      7.00  55.00   0.50    0.20    --   41.22 -54.00  90.00   96
 65  ω     22.00  66.00   0.50    0.20    --   41.22 -77.00  60.00   88
 66  ω     24.00  63.00   0.50    0.20    --   41.22 -89.00-180.00   78
 67  ω    -22.00   9.00   0.50    0.20    --   41.22 -89.00-180.00   62
 68  ω     26.00  52.00   0.50    0.20    --   41.22  65.00 -90.00   52
 69  ω     64.00 112.00   0.50    0.27    --  101.00 -59.00 120.00   96
 70  ω     49.00  79.00   0.50    0.27    --  101.00 -42.00 -30.00   60
 71  ω    131.00 157.00   0.50    0.27    --  101.00   8.00 -60.00   52
 72  ω     75.00 101.00   0.50    0.27    --  101.00   8.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0975340000
_diffrn_orient_matrix_UB_12      0.0531343000
_diffrn_orient_matrix_UB_13      -0.0065289000
_diffrn_orient_matrix_UB_21      0.0730941000
_diffrn_orient_matrix_UB_22      0.0029451000
_diffrn_orient_matrix_UB_23      0.1924650000
_diffrn_orient_matrix_UB_31      0.2585014000
_diffrn_orient_matrix_UB_32      -0.0209023000
_diffrn_orient_matrix_UB_33      0.0104209000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2142
_reflns_number_total             2368
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.55
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.047
_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)+(0.0583P)²+0.3274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1023
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C14(H14), C10(H10), C12(H12), C9(H9), C8(H8), C6(H6),
 C13(H13), C7(H7)
2.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61400(15) 0.54979(3) 0.69009(10) 0.0212(2) Uani 1 1 d . . . . .
O2 O 0.27716(16) 0.50313(3) 0.60255(11) 0.0248(2) Uani 1 1 d . . . . .
O3 O 0.04622(15) 0.57073(3) 0.36071(11) 0.0242(2) Uani 1 1 d . . . . .
H3 H -0.0088 0.5444 0.3906 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.65160(18) 0.62601(4) 0.56505(12) 0.0205(2) Uani 1 1 d . . . . .
C11 C 0.3358(2) 0.66263(4) 0.33373(14) 0.0191(3) Uani 1 1 d . . . . .
C3 C 0.2770(2) 0.57962(4) 0.46261(14) 0.0198(3) Uani 1 1 d . . . . .
C4 C 0.4142(2) 0.62106(4) 0.45388(14) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.7402(2) 0.59223(4) 0.67366(15) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.3808(2) 0.54171(4) 0.58614(15) 0.0201(3) Uani 1 1 d . . . . .
C16 C 0.5123(2) 0.69830(4) 0.32233(15) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.6782 0.6956 0.3924 0.026 Uiso 1 1 calc R . . . .
C15 C 0.4471(2) 0.73751(4) 0.20996(16) 0.0238(3) Uani 1 1 d . . . . .
H15 H 0.5687 0.7612 0.2032 0.029 Uiso 1 1 calc R . . . .
C5 C 0.9903(2) 0.59413(4) 0.79362(15) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.2044(2) 0.74228(4) 0.10725(16) 0.0245(3) Uani 1 1 d . . . . .
H14 H 0.1602 0.7688 0.0294 0.029 Uiso 1 1 calc R . . . .
C10 C 1.1442(2) 0.63469(5) 0.79321(15) 0.0241(3) Uani 1 1 d . . . . .
H10 H 1.0861 0.6614 0.7175 0.029 Uiso 1 1 calc R . . . .
C12 C 0.0912(2) 0.66831(4) 0.23131(15) 0.0228(3) Uani 1 1 d . . . . .
H12 H -0.0319 0.6450 0.2383 0.027 Uiso 1 1 calc R . . . .
C9 C 1.3821(2) 0.63602(5) 0.90343(16) 0.0272(3) Uani 1 1 d . . . . .
H9 H 1.4868 0.6636 0.9024 0.033 Uiso 1 1 calc R . . . .
C8 C 1.4682(2) 0.59735(5) 1.01520(16) 0.0270(3) Uani 1 1 d . . . . .
H8 H 1.6313 0.5984 1.0903 0.032 Uiso 1 1 calc R . . . .
C6 C 1.0780(3) 0.55549(5) 0.90614(18) 0.0326(3) Uani 1 1 d . . . . .
H6 H 0.9744 0.5277 0.9071 0.039 Uiso 1 1 calc R . . . .
C13 C 0.0275(2) 0.70777(5) 0.11969(16) 0.0255(3) Uani 1 1 d . . . . .
H13 H -0.1389 0.7112 0.0511 0.031 Uiso 1 1 calc R . . . .
C7 C 1.3158(3) 0.55723(5) 1.01702(17) 0.0327(3) Uani 1 1 d . . . . .
H7 H 1.3738 0.5309 1.0941 0.039 Uiso 1 1 calc R . . . .


_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 1.3748(14) . ?
O1 C2 1.3647(14) . ?
O2 C2 1.2199(14) . ?
O3 H3 0.8400 . ?
O3 C3 1.3517(14) . ?
N1 C4 1.3943(15) . ?
N1 C1 1.2791(15) . ?
C11 C4 1.4825(16) . ?
C11 C16 1.4068(16) . ?
C11 C12 1.4025(16) . ?
C3 C4 1.3727(16) . ?
C3 C2 1.4482(16) . ?
C1 C5 1.4724(16) . ?
C16 H16 0.9500 . ?
C16 C15 1.3895(17) . ?
C15 H15 0.9500 . ?
C15 C14 1.3920(17) . ?
C5 C10 1.3965(17) . ?
C5 C6 1.3929(18) . ?
C14 H14 0.9500 . ?
C14 C13 1.3894(18) . ?
C10 H10 0.9500 . ?
C10 C9 1.3877(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3904(17) . ?
C9 H9 0.9500 . ?
C9 C8 1.3885(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.3836(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3900(19) . ?
C13 H13 0.9500 . ?
C7 H7 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
C2 O1 C1 119.98(9) . . ?
C3 O3 H3 109.5 . . ?
C1 N1 C4 120.26(10) . . ?
C16 C11 C4 119.03(10) . . ?
C12 C11 C4 122.75(10) . . ?
C12 C11 C16 118.22(11) . . ?
O3 C3 C4 124.37(11) . . ?
O3 C3 C2 115.94(10) . . ?
C4 C3 C2 119.68(11) . . ?
N1 C4 C11 114.63(10) . . ?
C3 C4 N1 119.25(10) . . ?
C3 C4 C11 126.13(11) . . ?
O1 C1 C5 112.43(10) . . ?
N1 C1 O1 123.83(11) . . ?
N1 C1 C5 123.74(10) . . ?
O1 C2 C3 117.00(10) . . ?
O2 C2 O1 117.94(10) . . ?
O2 C2 C3 125.05(11) . . ?
C11 C16 H16 119.6 . . ?
C15 C16 C11 120.84(11) . . ?
C15 C16 H16 119.6 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C14 120.31(11) . . ?
C14 C15 H15 119.8 . . ?
C10 C5 C1 119.86(11) . . ?
C6 C5 C1 120.89(11) . . ?
C6 C5 C10 119.24(12) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 C15 119.32(11) . . ?
C13 C14 H14 120.3 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 119.98(11) . . ?
C9 C10 H10 120.0 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.50(11) . . ?
C13 C12 H12 119.7 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.42(12) . . ?
C8 C9 H9 119.8 . . ?
C9 C8 H8 120.1 . . ?
C7 C8 C9 119.87(12) . . ?
C7 C8 H8 120.1 . . ?
C5 C6 H6 119.8 . . ?
C7 C6 C5 120.48(12) . . ?
C7 C6 H6 119.8 . . ?
C14 C13 C12 120.78(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C8 C7 C6 120.01(12) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?

_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 1.467
_oxdiff_exptl_absorpt_empirical_full_min 0.553
####################################################################### 
# 
# 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_7076-11026_smi7
_database_code_depnum_ccdc_archive 'CCDC 1939720'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2019-07-10 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N O4'
_chemical_formula_sum            'C15 H15 N O4'
_chemical_formula_weight         273.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.8451(3)
_cell_length_b                   17.0778(6)
_cell_length_c                   9.7116(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.581(3)
_cell_angle_gamma                90
_cell_volume                     1298.59(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4657
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.4660
_cell_measurement_theta_min      2.8510
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             576
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14318
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         2.862
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -72.00    6.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000  120.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   65.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000 -120.0000 45

#__ type_ start__ end____ width___ exp.time_
  3 omega  -19.00   88.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178   19.0000   30.0000 107

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00  -53.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803 -178.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -78.00  -49.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  132.0000   42.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega  -89.00    1.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803  -77.0000 -150.0000 90

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00   36.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -46.00  -14.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -77.0000   90.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   23.00   48.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   77.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  -47.00  -21.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.5803   77.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  178.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega   26.00   63.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       23.5178  -99.0000    0.0000 37
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0010649000
_diffrn_orient_matrix_UB_12      -0.0411368000
_diffrn_orient_matrix_UB_13      -0.0100962000
_diffrn_orient_matrix_UB_21      -0.0025358000
_diffrn_orient_matrix_UB_22      -0.0057227000
_diffrn_orient_matrix_UB_23      0.0721780000
_diffrn_orient_matrix_UB_31      -0.0905502000
_diffrn_orient_matrix_UB_32      0.0006543000
_diffrn_orient_matrix_UB_33      -0.0065511000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2563
_reflns_number_total             2988
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.030
_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)+(0.0425P)²+0.6786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H7BC)=Sof(H7BD)=Sof(H5BC)=Sof(H5BD)=Sof(C6)=Sof(H6A)=Sof(H6B)=1-FVAR(1)
 Sof(H7AA)=Sof(H7AB)=Sof(H5AA)=Sof(H5AB)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7AA,H7AB), C7(H7BC,H7BD), C5(H5AA,H5AB), C5(H5BC,H5BD), C6A(H6AA,H6AB),
 C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C12(H12), C11(H11), C10(H10)
3.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.31555(11) 0.50339(5) 0.31819(9) 0.0172(2) Uani 1 1 d . . . . .
O3 O 0.17781(13) 0.63430(5) 0.37189(9) 0.0218(2) Uani 1 1 d . . . . .
O4 O 0.31048(13) 0.33673(6) 0.42854(10) 0.0247(2) Uani 1 1 d . . . . .
O2 O 0.11320(13) 0.66666(6) 0.15049(10) 0.0260(2) Uani 1 1 d . . . . .
N1 N 0.34695(13) 0.43076(6) 0.13176(11) 0.0179(2) Uani 1 1 d . . . . .
C14 C 0.17307(16) 0.62122(7) 0.23571(13) 0.0167(3) Uani 1 1 d . . . . .
C3 C 0.24933(15) 0.54529(7) 0.20503(12) 0.0160(2) Uani 1 1 d . . . . .
C2 C 0.26842(15) 0.50069(7) 0.08958(13) 0.0161(2) Uani 1 1 d . . . . .
C8 C 0.22289(15) 0.51185(7) -0.05904(13) 0.0164(3) Uani 1 1 d . . . . .
C1 C 0.37118(15) 0.43564(7) 0.26431(13) 0.0171(3) Uani 1 1 d . . . . .
C4 C 0.44766(17) 0.37617(8) 0.36372(14) 0.0202(3) Uani 1 1 d . . . . .
H4 H 0.5243 0.4028 0.4354 0.024 Uiso 1 1 calc R . . . .
C13 C 0.11548(16) 0.57117(8) -0.11179(13) 0.0195(3) Uani 1 1 d . . . . .
H13 H 0.0681 0.6077 -0.0510 0.023 Uiso 1 1 calc R . . . .
C9 C 0.28963(17) 0.45796(8) -0.15053(14) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.3617 0.4169 -0.1157 0.026 Uiso 1 1 calc R . . . .
C12 C 0.07756(17) 0.57694(8) -0.25338(14) 0.0230(3) Uani 1 1 d . . . . .
H12 H 0.0042 0.6174 -0.2887 0.028 Uiso 1 1 calc R . . . .
C7 C 0.54714(17) 0.31282(8) 0.29116(15) 0.0232(3) Uani 1 1 d . . . . .
H7AA H 0.6447 0.2931 0.3509 0.028 Uiso 0.483(9) 1 calc R . P A 1
H7AB H 0.5890 0.3321 0.2032 0.028 Uiso 0.483(9) 1 calc R . P A 1
H7BC H 0.5363 0.3202 0.1899 0.028 Uiso 0.517(9) 1 calc R . P A 2
H7BD H 0.6697 0.3145 0.3223 0.028 Uiso 0.517(9) 1 calc R . P A 2
C11 C 0.14589(18) 0.52406(9) -0.34352(14) 0.0246(3) Uani 1 1 d . . . . .
H11 H 0.1208 0.5288 -0.4401 0.030 Uiso 1 1 calc R . . . .
C15 C 0.0911(2) 0.70479(8) 0.41154(15) 0.0285(3) Uani 1 1 d . . . . .
H15A H 0.1422 0.7502 0.3683 0.043 Uiso 1 1 calc GR . . . .
H15B H 0.1025 0.7105 0.5121 0.043 Uiso 1 1 calc GR . . . .
H15C H -0.0301 0.7014 0.3811 0.043 Uiso 1 1 calc GR . . . .
C10 C 0.25117(19) 0.46427(9) -0.29147(14) 0.0257(3) Uani 1 1 d . . . . .
H10 H 0.2971 0.4275 -0.3526 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2989(2) 0.25866(10) 0.3773(2) 0.0461(5) Uani 1 1 d . . . . .
H5AA H 0.3331 0.2213 0.4520 0.055 Uiso 0.483(9) 1 calc R . P A 1
H5AB H 0.1795 0.2470 0.3448 0.055 Uiso 0.483(9) 1 calc R . P A 1
H5BC H 0.2117 0.2557 0.2993 0.055 Uiso 0.517(9) 1 calc R . P A 2
H5BD H 0.2648 0.2228 0.4508 0.055 Uiso 0.517(9) 1 calc R . P A 2
C6A C 0.4076(6) 0.2499(2) 0.2666(5) 0.0266(11) Uani 0.483(9) 1 d . . P A 1
H6AA H 0.3432 0.2584 0.1769 0.032 Uiso 0.483(9) 1 calc R . P A 1
H6AB H 0.4587 0.1969 0.2673 0.032 Uiso 0.483(9) 1 calc R . P A 1
C6 C 0.4681(6) 0.23553(19) 0.3308(6) 0.0326(12) Uani 0.517(9) 1 d . . P A 2
H6A H 0.4558 0.1997 0.2506 0.039 Uiso 0.517(9) 1 calc R . P A 2
H6B H 0.5380 0.2096 0.4060 0.039 Uiso 0.517(9) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.3850(15) . ?
O1 C1 1.3533(15) . ?
O3 C14 1.3394(15) . ?
O3 C15 1.4466(16) . ?
O4 C4 1.4466(15) . ?
O4 C5 1.4240(18) . ?
O2 C14 1.2081(16) . ?
N1 C2 1.3937(16) . ?
N1 C1 1.2921(16) . ?
C14 C3 1.4663(17) . ?
C3 C2 1.3713(17) . ?
C2 C8 1.4774(17) . ?
C8 C13 1.3946(18) . ?
C8 C9 1.4032(18) . ?
C1 C4 1.5004(18) . ?
C4 C7 1.5314(18) . ?
C13 C12 1.3921(18) . ?
C9 C10 1.3873(19) . ?
C12 C11 1.388(2) . ?
C7 C6A 1.541(4) . ?
C7 C6 1.518(4) . ?
C11 C10 1.389(2) . ?
C5 C6A 1.421(4) . ?
C5 C6 1.482(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C3 104.42(9) . . ?
C14 O3 C15 114.66(10) . . ?
C5 O4 C4 108.48(11) . . ?
C1 N1 C2 105.80(10) . . ?
O3 C14 C3 111.20(10) . . ?
O2 C14 O3 123.70(12) . . ?
O2 C14 C3 125.10(12) . . ?
O1 C3 C14 115.67(10) . . ?
C2 C3 O1 107.88(11) . . ?
C2 C3 C14 136.39(12) . . ?
N1 C2 C8 118.23(11) . . ?
C3 C2 N1 107.73(11) . . ?
C3 C2 C8 134.03(12) . . ?
C13 C8 C2 123.79(11) . . ?
C13 C8 C9 118.99(12) . . ?
C9 C8 C2 117.19(12) . . ?
O1 C1 C4 117.10(11) . . ?
N1 C1 O1 114.17(11) . . ?
N1 C1 C4 128.71(12) . . ?
O4 C4 C1 108.46(10) . . ?
O4 C4 C7 106.60(10) . . ?
C1 C4 C7 112.15(11) . . ?
C12 C13 C8 120.08(12) . . ?
C10 C9 C8 120.46(13) . . ?
C11 C12 C13 120.64(13) . . ?
C4 C7 C6A 100.71(17) . . ?
C6 C7 C4 105.65(15) . . ?
C12 C11 C10 119.54(12) . . ?
C9 C10 C11 120.27(13) . . ?
O4 C5 C6 108.49(18) . . ?
C6A C5 O4 109.52(18) . . ?
C5 C6A C7 105.3(2) . . ?
C5 C6 C7 103.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_10681-13632_agf7
_database_code_depnum_ccdc_archive 'CCDC 1941719'
loop_
_audit_author_name
_audit_author_address
'Olesya Khoroshilova'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2022-05-11 deposited with the CCDC.	2022-06-21 downloaded from the CCDC.
;
_audit_creation_date             2019-07-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O3'
_chemical_formula_sum            'C14 H15 N O3'
_chemical_formula_weight         245.27
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H15 N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.5893(5)
_cell_length_b                   11.4528(9)
_cell_length_c                   21.4631(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2603.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6810
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.6210
_cell_measurement_theta_min      3.8400
_shelx_estimated_absorpt_T_max   0.869
_shelx_estimated_absorpt_T_min   0.714
_exptl_absorpt_coefficient_mu    0.723
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64145
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1063
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13744
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.999
_diffrn_reflns_theta_min         4.119
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      9.00  43.00   1.00    1.28    --   40.38 -38.00-180.00   34
  2  ω     47.00 104.00   1.00    5.11    --  113.00 -95.00-120.00   57
  3  ω     57.00 115.00   1.00    5.11    --  113.00-112.00-180.00   58
  4  ω     84.00 176.00   1.00    5.11    --  113.00  30.00  90.00   92
  5  ω    133.00 167.00   1.00    5.11    --  113.00 112.00 150.00   34
  6  ω    102.00 134.00   1.00    5.11    --  113.00 112.00  90.00   32
  7  ω    108.00 178.00   1.00    5.11    --  113.00 112.00 -60.00   70
  8  ω    -93.00 -48.00   1.00    1.28    --  -40.38 125.00 105.00   45
  9  ω   -107.00 -14.00   1.00    1.28    --  -40.38 -57.00 -60.00   93
 10  ω   -106.00 -37.00   1.00    1.28    --  -40.38 178.00-180.00   69
 11  ω     40.00  82.00   1.00    5.11    --  113.00 -30.00-180.00   42
 12  ω     99.00 127.00   1.00    5.11    --  113.00 -30.00-180.00   28
 13  ω     60.00 107.00   1.00    5.11    --  113.00-112.00 150.00   47
 14  ω     81.00 107.00   1.00    5.11    --  113.00 -95.00-180.00   26
 15  ω     54.00 121.00   1.00    5.11    --  113.00 -30.00  30.00   67
 16  ω      2.00  66.00   1.00    1.28    --   40.38 -38.00  30.00   64
 17  ω     84.00 110.00   1.00    5.11    --  113.00-112.00 120.00   26
 18  ω     95.00 141.00   1.00    5.11    --  113.00 -45.00  90.00   46
 19  ω     37.00  81.00   1.00    5.11    --  113.00-112.00 120.00   44
 20  ω   -115.00 -14.00   1.00    1.28    --  -40.38 -38.00  90.00  101
 21  ω    -71.00 -37.00   1.00    1.28    --  -40.38-178.00-180.00   34
 22  ω    105.00 130.00   1.00    1.28    --   40.38 178.00  90.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0085749000
_diffrn_orient_matrix_UB_12      -0.1236726000
_diffrn_orient_matrix_UB_13      -0.0278352000
_diffrn_orient_matrix_UB_21      0.0153693000
_diffrn_orient_matrix_UB_22      0.0514021000
_diffrn_orient_matrix_UB_23      -0.0659198000
_diffrn_orient_matrix_UB_31      0.1443080000
_diffrn_orient_matrix_UB_32      -0.0127196000
_diffrn_orient_matrix_UB_33      0.0053366000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4203
_reflns_number_total             4988
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         4988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0722
_refine_ls_restrained_S_all      1.058
_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)+(0.1246P)²+0.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1897
_refine_ls_wR_factor_ref         0.2183
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(5)
 0.2(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C10A(H10A), C14(H14), C11A(H11A), C14A(H14A), C13(H13), C10(H10), C12A(H12A),
 C13A(H13A), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C6(H6A,H6B,H6C), C6A(H6AA,H6AB,H6AC), C8(H8A,H8B,H8C),
 C8A(H8AA,H8AB,H8AC), C7(H7A,H7B,H7C)
3.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5226(3) 0.6401(3) 0.42958(14) 0.0429(7) Uani 1 1 d . . . . .
O1A O 0.0215(3) 0.3149(3) 0.33322(15) 0.0420(7) Uani 1 1 d . . . . .
O2A O -0.0273(3) 0.1778(4) 0.40215(18) 0.0566(10) Uani 1 1 d . . . . .
O3 O 0.3187(3) 0.4563(4) 0.5205(2) 0.0613(11) Uani 1 1 d . . . . .
H3 H 0.3796 0.4113 0.5275 0.092 Uiso 1 1 calc GR . . . .
O2 O 0.5681(3) 0.5125(4) 0.50343(19) 0.0569(10) Uani 1 1 d . . . . .
O3A O 0.2221(3) 0.1431(4) 0.4331(2) 0.0633(12) Uani 1 1 d . . . . .
H3A H 0.1584 0.1044 0.4439 0.095 Uiso 1 1 calc GR . . . .
N1 N 0.3157(4) 0.6833(4) 0.40120(17) 0.0416(8) Uani 1 1 d . . . . .
N1A N 0.2278(3) 0.3780(4) 0.31821(17) 0.0398(8) Uani 1 1 d . . . . .
C9 C 0.1319(4) 0.5910(4) 0.4470(2) 0.0400(9) Uani 1 1 d . . . . .
C4 C 0.2709(4) 0.5990(4) 0.44316(19) 0.0369(9) Uani 1 1 d . . . . .
C10A C 0.4795(4) 0.3907(4) 0.3496(2) 0.0450(10) Uani 1 1 d . . . . .
H10A H 0.4367 0.4564 0.3328 0.054 Uiso 1 1 calc R . . . .
C1 C 0.4331(4) 0.6988(4) 0.39588(19) 0.0399(9) Uani 1 1 d . . . . .
C9A C 0.4104(4) 0.2932(4) 0.3683(2) 0.0381(9) Uani 1 1 d . . . . .
C2 C 0.4875(4) 0.5586(4) 0.4723(2) 0.0405(10) Uani 1 1 d . . . . .
C4A C 0.2734(4) 0.2942(4) 0.36039(19) 0.0370(9) Uani 1 1 d . . . . .
C2A C 0.0553(4) 0.2350(4) 0.3774(2) 0.0431(10) Uani 1 1 d . . . . .
C5A C 0.0569(4) 0.4674(4) 0.2580(2) 0.0436(10) Uani 1 1 d . . . . .
C3A C 0.1878(4) 0.2241(4) 0.3900(2) 0.0407(9) Uani 1 1 d . . . . .
C14 C 0.0705(4) 0.4887(5) 0.4630(2) 0.0481(11) Uani 1 1 d . . . . .
H14 H 0.1176 0.4198 0.4712 0.058 Uiso 1 1 calc R . . . .
C3 C 0.3534(4) 0.5373(5) 0.4778(2) 0.0423(10) Uani 1 1 d . . . . .
C11A C 0.6093(5) 0.3926(5) 0.3552(3) 0.0550(13) Uani 1 1 d . . . . .
H11A H 0.6550 0.4605 0.3434 0.066 Uiso 1 1 calc R . . . .
C1A C 0.1117(4) 0.3850(4) 0.30661(19) 0.0375(9) Uani 1 1 d . . . . .
C14A C 0.4760(5) 0.1970(5) 0.3912(3) 0.0570(13) Uani 1 1 d . . . . .
H14A H 0.4310 0.1294 0.4040 0.068 Uiso 1 1 calc R . . . .
C5 C 0.4927(5) 0.7841(5) 0.3504(2) 0.0489(11) Uani 1 1 d . . . . .
C13 C -0.0606(5) 0.4870(7) 0.4669(3) 0.0625(15) Uani 1 1 d . . . . .
H13 H -0.1025 0.4164 0.4775 0.075 Uiso 1 1 calc R . . . .
C10 C 0.0609(5) 0.6931(5) 0.4342(2) 0.0524(12) Uani 1 1 d . . . . .
H10 H 0.1024 0.7630 0.4220 0.063 Uiso 1 1 calc R . . . .
C12A C 0.6733(5) 0.2963(6) 0.3779(3) 0.0588(14) Uani 1 1 d . . . . .
H12A H 0.7627 0.2972 0.3812 0.071 Uiso 1 1 calc R . . . .
C7A C 0.1514(6) 0.5638(6) 0.2456(3) 0.0703(18) Uani 1 1 d . . . . .
H7AA H 0.2287 0.5301 0.2280 0.105 Uiso 1 1 calc GR . . . .
H7AB H 0.1715 0.6038 0.2847 0.105 Uiso 1 1 calc GR . . . .
H7AC H 0.1154 0.6198 0.2160 0.105 Uiso 1 1 calc GR . . . .
C13A C 0.6062(5) 0.1994(6) 0.3955(3) 0.0646(16) Uani 1 1 d . . . . .
H13A H 0.6498 0.1329 0.4108 0.078 Uiso 1 1 calc R . . . .
C6 C 0.5866(7) 0.8631(7) 0.3850(3) 0.0738(19) Uani 1 1 d . . . . .
H6A H 0.6505 0.8148 0.4056 0.111 Uiso 1 1 calc GR . . . .
H6B H 0.5415 0.9094 0.4162 0.111 Uiso 1 1 calc GR . . . .
H6C H 0.6279 0.9154 0.3551 0.111 Uiso 1 1 calc GR . . . .
C11 C -0.0696(5) 0.6901(7) 0.4395(3) 0.0630(15) Uani 1 1 d . . . . .
H11 H -0.1176 0.7588 0.4323 0.076 Uiso 1 1 calc R . . . .
C12 C -0.1305(5) 0.5860(8) 0.4556(3) 0.0706(19) Uani 1 1 d . . . . .
H12 H -0.2199 0.5837 0.4587 0.085 Uiso 1 1 calc R . . . .
C6A C 0.0358(8) 0.3961(6) 0.1983(3) 0.0781(19) Uani 1 1 d . . . . .
H6AA H -0.0265 0.3346 0.2064 0.117 Uiso 1 1 calc GR . . . .
H6AB H 0.1157 0.3606 0.1853 0.117 Uiso 1 1 calc GR . . . .
H6AC H 0.0046 0.4476 0.1652 0.117 Uiso 1 1 calc GR . . . .
C8 C 0.3889(7) 0.8612(8) 0.3218(4) 0.087(2) Uani 1 1 d . . . . .
H8A H 0.3432 0.9017 0.3551 0.130 Uiso 1 1 calc GR . . . .
H8B H 0.3300 0.8123 0.2982 0.130 Uiso 1 1 calc GR . . . .
H8C H 0.4274 0.9188 0.2939 0.130 Uiso 1 1 calc GR . . . .
C8A C -0.0657(6) 0.5211(7) 0.2814(3) 0.0721(18) Uani 1 1 d . . . . .
H8AA H -0.0507 0.5599 0.3214 0.108 Uiso 1 1 calc GR . . . .
H8AB H -0.1292 0.4597 0.2868 0.108 Uiso 1 1 calc GR . . . .
H8AC H -0.0963 0.5785 0.2510 0.108 Uiso 1 1 calc GR . . . .
C7 C 0.5603(9) 0.7170(7) 0.2996(3) 0.092(3) Uani 1 1 d . . . . .
H7A H 0.4992 0.6694 0.2766 0.138 Uiso 1 1 calc GR . . . .
H7B H 0.6244 0.6662 0.3184 0.138 Uiso 1 1 calc GR . . . .
H7C H 0.6012 0.7720 0.2710 0.138 Uiso 1 1 calc GR . . . .


_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 1.368(5) . ?
O1 C2 1.361(5) . ?
O1A C2A 1.366(5) . ?
O1A C1A 1.372(5) . ?
O2A C2A 1.215(6) . ?
O3 H3 0.8400 . ?
O3 C3 1.355(6) . ?
O2 C2 1.205(6) . ?
O3A H3A 0.8400 . ?
O3A C3A 1.359(6) . ?
N1 C4 1.403(6) . ?
N1 C1 1.262(6) . ?
N1A C4A 1.405(5) . ?
N1A C1A 1.257(6) . ?
C9 C4 1.477(6) . ?
C9 C14 1.383(7) . ?
C9 C10 1.417(7) . ?
C4 C3 1.347(6) . ?
C10A H10A 0.9500 . ?
C10A C9A 1.394(7) . ?
C10A C11A 1.380(7) . ?
C1 C5 1.518(6) . ?
C9A C4A 1.461(6) . ?
C9A C14A 1.392(7) . ?
C2 C3 1.446(6) . ?
C4A C3A 1.368(6) . ?
C2A C3A 1.434(6) . ?
C5A C1A 1.523(6) . ?
C5A C7A 1.513(8) . ?
C5A C6A 1.535(8) . ?
C5A C8A 1.522(7) . ?
C14 H14 0.9500 . ?
C14 C13 1.391(7) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.384(8) . ?
C14A H14A 0.9500 . ?
C14A C13A 1.382(8) . ?
C5 C6 1.536(8) . ?
C5 C8 1.538(8) . ?
C5 C7 1.514(8) . ?
C13 H13 0.9500 . ?
C13 C12 1.376(10) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(7) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.370(9) . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C13A H13A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.399(11) . ?
C12 H12 0.9500 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C2 O1 C1 120.3(3) . . ?
C2A O1A C1A 119.9(3) . . ?
C3 O3 H3 109.5 . . ?
C3A O3A H3A 109.5 . . ?
C1 N1 C4 119.2(4) . . ?
C1A N1A C4A 120.4(4) . . ?
C14 C9 C4 122.4(4) . . ?
C14 C9 C10 119.9(4) . . ?
C10 C9 C4 117.8(5) . . ?
N1 C4 C9 114.6(4) . . ?
C3 C4 N1 119.7(4) . . ?
C3 C4 C9 125.6(4) . . ?
C9A C10A H10A 119.6 . . ?
C11A C10A H10A 119.6 . . ?
C11A C10A C9A 120.7(5) . . ?
O1 C1 C5 111.6(4) . . ?
N1 C1 O1 124.4(4) . . ?
N1 C1 C5 123.9(4) . . ?
C10A C9A C4A 118.8(4) . . ?
C14A C9A C10A 118.3(4) . . ?
C14A C9A C4A 122.9(5) . . ?
O1 C2 C3 116.0(4) . . ?
O2 C2 O1 118.7(4) . . ?
O2 C2 C3 125.3(4) . . ?
N1A C4A C9A 114.9(4) . . ?
C3A C4A N1A 118.2(4) . . ?
C3A C4A C9A 126.8(4) . . ?
O1A C2A C3A 116.5(4) . . ?
O2A C2A O1A 118.4(4) . . ?
O2A C2A C3A 125.1(4) . . ?
C1A C5A C6A 107.3(4) . . ?
C7A C5A C1A 108.7(4) . . ?
C7A C5A C6A 109.7(5) . . ?
C7A C5A C8A 109.1(5) . . ?
C8A C5A C1A 110.5(4) . . ?
C8A C5A C6A 111.5(5) . . ?
O3A C3A C4A 122.6(4) . . ?
O3A C3A C2A 116.7(4) . . ?
C4A C3A C2A 120.6(4) . . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.7(6) . . ?
C13 C14 H14 120.1 . . ?
O3 C3 C2 115.9(4) . . ?
C4 C3 O3 123.8(4) . . ?
C4 C3 C2 120.3(4) . . ?
C10A C11A H11A 119.8 . . ?
C10A C11A C12A 120.3(5) . . ?
C12A C11A H11A 119.8 . . ?
O1A C1A C5A 112.5(3) . . ?
N1A C1A O1A 124.2(4) . . ?
N1A C1A C5A 123.2(4) . . ?
C9A C14A H14A 119.8 . . ?
C13A C14A C9A 120.4(5) . . ?
C13A C14A H14A 119.8 . . ?
C1 C5 C6 109.7(4) . . ?
C1 C5 C8 109.2(4) . . ?
C6 C5 C8 108.5(6) . . ?
C7 C5 C1 109.4(5) . . ?
C7 C5 C6 109.9(6) . . ?
C7 C5 C8 110.0(6) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(6) . . ?
C11 C10 H10 120.3 . . ?
C11A C12A H12A 120.4 . . ?
C13A C12A C11A 119.3(5) . . ?
C13A C12A H12A 120.4 . . ?
C5A C7A H7AA 109.5 . . ?
C5A C7A H7AB 109.5 . . ?
C5A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C14A C13A H13A 119.5 . . ?
C12A C13A C14A 121.0(6) . . ?
C12A C13A H13A 119.5 . . ?
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 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(6) . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.9(5) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5A C8A H8AA 109.5 . . ?
C5A C8A H8AB 109.5 . . ?
C5A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_olex2_date_sample_data_collection 2019-07-18
_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 3.098
_oxdiff_exptl_absorpt_empirical_full_min 0.354
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(5)
2 0.2(5)

