# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_tmnb19_vt_01_250_00abs
_database_code_depnum_ccdc_archive 'CCDC 1991869'
loop_
_audit_author_name
_audit_author_address
'Vasyl Kinzhybalo'
;Institute of Low Temperature and Structure Research
Poland
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0(C), 0.5(C18 H22 N2 O4)'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_melting_point          ?
_chemical_oxdiff_formula         C9H11NO2
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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   15.113(9)
_cell_length_b                   7.205(4)
_cell_length_c                   8.356(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     909.9(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3292
_cell_measurement_temperature    250.00(10)
_cell_measurement_theta_max      27.8680
_cell_measurement_theta_min      3.6260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.1415
-1 0 0 0.1102
0 0 1 0.2146
-1 0 -2 0.1283
0 -1 0 0.3356
0 1 0 0.3659
2 0 -1 0.1698
-2 0 1 0.1495
5 0 2 0.1524
-5 0 -2 0.0938
5 -1 0 0.1252
5 1 1 0.1585
-2 -2 5 0.2319
-5 3 2 0.2988
5 1 -3 0.2164

_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.246
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
1.0011 -0.0007 0.0002 -0.0158 0.0289 0.0335
-1.0011 0.0007 -0.0002 0.0158 -0.0289 -0.0335
-0.0011 -0.0009 1.0005 -0.0455 0.0422 -0.0580
-0.9988 0.0025 -2.0012 0.1068 -0.1133 0.0826
-0.0011 -1.0018 -0.0002 -0.0765 -0.0602 0.0160
0.0011 1.0018 0.0002 0.0765 0.0602 -0.0160
2.0034 -0.0005 -1.0001 0.0138 0.0157 0.1250
-2.0034 0.0005 1.0001 -0.0138 -0.0157 -0.1250
5.0034 -0.0052 2.0020 -0.1701 0.2291 0.0512
-5.0034 0.0052 -2.0020 0.1701 -0.2291 -0.0512
5.0046 -1.0052 0.0008 -0.1556 0.0845 0.1833
5.0056 0.9975 1.0018 -0.0481 0.2470 0.0932
-2.0102 -2.0067 5.0016 -0.3487 0.0327 -0.3251
-5.0047 3.0069 2.0007 0.2175 0.1202 -0.3314
5.0102 1.0011 -3.0002 0.1338 0.0783 0.3254

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13691
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.412
_diffrn_reflns_theta_min         2.696
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 104.00   1.00    4.00    --   13.60-178.00  90.00   72
  2  ω    -77.00 -32.00   1.00    4.00    --   13.60 178.00   0.00   45
  3  ω    -19.00  92.00   1.00    4.00    --   13.60  57.00  90.00  111
  4  ω    -64.00  46.00   1.00    4.00    --   13.60 -57.00 120.00  110
  5  ω     35.00 106.00   1.00    4.00    --   13.60 178.00 -30.00   71
  6  ω    -19.00  92.00   1.00    4.00    --   13.60  57.00-120.00  111
  7  ω    -50.00  11.00   1.00    4.00    --  -14.38  77.00 -60.00   61
  8  ω    -25.00  30.00   1.00    4.00    --  -14.38 -99.00 -60.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0157399000
_diffrn_orient_matrix_UB_12      0.0763500000
_diffrn_orient_matrix_UB_13      -0.0454124000
_diffrn_orient_matrix_UB_21      0.0289383000
_diffrn_orient_matrix_UB_22      0.0600096000
_diffrn_orient_matrix_UB_23      0.0422534000
_diffrn_orient_matrix_UB_31      0.0334222000
_diffrn_orient_matrix_UB_32      -0.0160139000
_diffrn_orient_matrix_UB_33      -0.0579878000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                832
_reflns_number_total             1285
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (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         0.128
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0513
_refine_ls_restrained_S_all      1.057
_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)+(0.0834P)²+0.1032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1384
_refine_ls_wR_factor_ref         0.1647
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: CG(0) H7B(0.5) H7A(0.5) H7C(0.5) H8B(0.5) H8A(0.5) H8C(0.5)
 H9A(0.5) H9B(0.5) H9C(0.5) O1(0.5) O2(0.5)
3.a Everything fixed:
 CG
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
3.c Idealised Me refined as rotating group:
 C7(H7B,H7A,H7C), C8(H8B,H8A,H8C), C9(H9A,H9B,H9C)
;
_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
CG C 0.105320 0.250000 0.570350 0.050 Uiso 0 2 d S T P . .
C1 C 0.12550(12) 0.250000 0.7361(2) 0.0503(5) Uani 1 2 d S T P . .
C2 C 0.03917(11) 0.250000 0.6792(2) 0.0516(5) Uani 1 2 d S T P . .
C3 C 0.01617(13) 0.250000 0.5178(2) 0.0539(5) Uani 1 2 d S T P . .
C4 C 0.08573(13) 0.250000 0.4096(2) 0.0554(5) Uani 1 2 d S T P . .
H4 H 0.073018 0.250000 0.299472 0.066 Uiso 1 2 calc RS T P . .
C5 C 0.17346(12) 0.250000 0.4584(2) 0.0518(5) Uani 1 2 d S T P . .
C6 C 0.19189(11) 0.250000 0.6210(2) 0.0504(5) Uani 1 2 d S T P . .
H6 H 0.251266 0.250000 0.654503 0.061 Uiso 1 2 calc RS T P . .
C7 C 0.14834(16) 0.250000 0.9123(2) 0.0737(7) Uani 1 2 d S T P . .
H7B H 0.141745 0.125506 0.954854 0.111 Uiso 0.5 1 calc GR . . . .
H7A H 0.108916 0.333662 0.968771 0.111 Uiso 0.5 1 calc GR . . . .
H7C H 0.209009 0.290832 0.926340 0.111 Uiso 0.5 1 calc GR . . . .
C8 C -0.07820(14) 0.250000 0.4586(3) 0.0768(7) Uani 1 2 d S T P . .
H8B H -0.114115 0.172412 0.527709 0.115 Uiso 0.5 1 calc GR . . . .
H8A H -0.080068 0.201802 0.350229 0.115 Uiso 0.5 1 calc GR . . . .
H8C H -0.101069 0.375786 0.459703 0.115 Uiso 0.5 1 calc GR . . . .
C9 C 0.24759(17) 0.250000 0.3365(3) 0.0769(7) Uani 1 2 d S T P . .
H9A H 0.232936 0.334158 0.249817 0.115 Uiso 0.5 1 calc GR . . . .
H9B H 0.255275 0.125637 0.294237 0.115 Uiso 0.5 1 calc GR . . . .
H9C H 0.302035 0.290205 0.387220 0.115 Uiso 0.5 1 calc GR . . . .
N1 N -0.03342(12) 0.250000 0.7976(2) 0.0728(6) Uani 1 2 d S T P . .
O1 O -0.0820(2) 0.1220(7) 0.8133(6) 0.1154(18) Uani 0.5 1 d . . . . .
O2 O -0.0406(2) 0.3947(7) 0.8756(6) 0.1181(17) Uani 0.5 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
C1 C2 1.388(3) . ?
C1 C6 1.390(3) . ?
C1 C7 1.513(3) . ?
C2 C3 1.393(3) . ?
C2 N1 1.477(2) . ?
C3 C4 1.387(3) . ?
C3 C8 1.510(3) . ?
C4 H4 0.9400 . ?
C4 C5 1.387(3) . ?
C5 C6 1.387(3) . ?
C5 C9 1.514(3) . ?
C6 H6 0.9400 . ?
C7 H7B 0.9700 . ?
C7 H7B 0.970(8) 7_565 ?
C7 H7A 0.9700 . ?
C7 H7A 0.970(19) 7_565 ?
C7 H7C 0.970(12) 7_565 ?
C7 H7C 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8B 0.970(17) 7_565 ?
C8 H8A 0.970(12) 7_565 ?
C8 H8A 0.9700 . ?
C8 H8C 0.9700 . ?
C8 H8C 0.970(5) 7_565 ?
C9 H9A 0.97(2) 7_565 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9B 0.970(8) 7_565 ?
C9 H9C 0.9700 . ?
C9 H9C 0.970(13) 7_565 ?
N1 O1 1.186(4) . ?
N1 O1 1.186(4) 7_565 ?
N1 O2 1.234(5) . ?
N1 O2 1.234(5) 7_565 ?

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 C1 C6 116.22(16) . . ?
C2 C1 C7 123.20(17) . . ?
C6 C1 C7 120.59(18) . . ?
C1 C2 C3 124.45(17) . . ?
C1 C2 N1 117.95(17) . . ?
C3 C2 N1 117.59(17) . . ?
C2 C3 C8 123.6(2) . . ?
C4 C3 C2 116.25(17) . . ?
C4 C3 C8 120.17(19) . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.21(17) . . ?
C5 C4 H4 118.9 . . ?
C4 C5 C9 120.61(18) . . ?
C6 C5 C4 118.68(17) . . ?
C6 C5 C9 120.70(18) . . ?
C1 C6 H6 118.9 . . ?
C5 C6 C1 122.20(17) . . ?
C5 C6 H6 118.9 . . ?
C1 C7 H7B 109.47(16) . 7_565 ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7A 109.5(4) . 7_565 ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7C 109.5(3) . 7_565 ?
C1 C7 H7C 109.5 . . ?
H7B C7 H7B 135.3 . 7_565 ?
H7B C7 H7A 109.5 . . ?
H7B C7 H7A 109.5 7_565 7_565 ?
H7B C7 H7A 35.3 . 7_565 ?
H7B C7 H7C 109.5 . . ?
H7B C7 H7C 76.8 . 7_565 ?
H7B C7 H7C 109.5 7_565 7_565 ?
H7A C7 H7B 35.3 . 7_565 ?
H7A C7 H7A 76.8 . 7_565 ?
H7A C7 H7C 135.3 . 7_565 ?
H7A C7 H7C 109.5 7_565 7_565 ?
H7A C7 H7C 109.5 . . ?
H7C C7 H7B 76.8 . 7_565 ?
H7C C7 H7A 135.3 . 7_565 ?
H7C C7 H7C 35.3 . 7_565 ?
C3 C8 H8B 109.5 . . ?
C3 C8 H8B 109.5(4) . 7_565 ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8A 109.5(3) . 7_565 ?
C3 C8 H8C 109.5 . . ?
C3 C8 H8C 109.47(10) . 7_565 ?
H8B C8 H8B 70.4 . 7_565 ?
H8B C8 H8A 109.5 7_565 7_565 ?
H8B C8 H8A 109.5 . . ?
H8B C8 H8A 138.2 . 7_565 ?
H8B C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 7_565 7_565 ?
H8B C8 H8C 42.0 . 7_565 ?
H8A C8 H8B 138.2 . 7_565 ?
H8A C8 H8A 42.0 . 7_565 ?
H8A C8 H8C 109.5 . . ?
H8A C8 H8C 70.4 . 7_565 ?
H8A C8 H8C 109.5 7_565 7_565 ?
H8C C8 H8B 42.0 . 7_565 ?
H8C C8 H8A 70.4 . 7_565 ?
H8C C8 H8C 138.2 . 7_565 ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9A 109.5(5) . 7_565 ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9B 109.47(17) . 7_565 ?
C5 C9 H9C 109.5(3) . 7_565 ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9A 77.4 . 7_565 ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9B 34.8 . 7_565 ?
H9A C9 H9B 109.5 7_565 7_565 ?
H9A C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 7_565 7_565 ?
H9A C9 H9C 135.0 . 7_565 ?
H9B C9 H9A 34.8 . 7_565 ?
H9B C9 H9B 135.0 . 7_565 ?
H9B C9 H9C 109.5 7_565 7_565 ?
H9B C9 H9C 77.4 . 7_565 ?
H9B C9 H9C 109.5 . . ?
H9C C9 H9A 135.0 . 7_565 ?
H9C C9 H9B 77.4 . 7_565 ?
H9C C9 H9C 34.8 . 7_565 ?
O1 N1 C2 122.3(3) . . ?
O1 N1 C2 122.3(3) 7_565 . ?
O1 N1 O1 102.1(4) . 7_565 ?
O1 N1 O2 123.0(2) . . ?
O1 N1 O2 123.0(2) 7_565 7_565 ?
O1 N1 O2 39.7(3) 7_565 . ?
O1 N1 O2 39.7(3) . 7_565 ?
O2 N1 C2 114.7(2) 7_565 . ?
O2 N1 C2 114.7(2) . . ?
O2 N1 O2 115.3(6) . 7_565 ?

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
C6 H6 O1 0.94 2.70 3.582(5) 157.2 6_657 yes
C7 H7B O2 0.97 2.67 3.514(5) 146.1 3_547 yes
C8 H8C CG 0.97 2.71 3.634(2) 159.7 3_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
C1 C2 C3 C4 0.000(0) . . . . ?
C1 C2 C3 C8 180.000(0) . . . . ?
C1 C2 N1 O1 113.1(3) . . . 7_565 ?
C1 C2 N1 O1 -113.1(3) . . . . ?
C1 C2 N1 O2 68.4(3) . . . . ?
C1 C2 N1 O2 -68.4(3) . . . 7_565 ?
C2 C1 C6 C5 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C3 C2 N1 O1 -66.9(3) . . . 7_565 ?
C3 C2 N1 O1 66.9(3) . . . . ?
C3 C2 N1 O2 111.6(3) . . . 7_565 ?
C3 C2 N1 O2 -111.6(3) . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C3 C4 C5 C9 180.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
C6 C1 C2 N1 180.000(0) . . . . ?
C7 C1 C2 C3 180.000(0) . . . . ?
C7 C1 C2 N1 0.000(0) . . . . ?
C7 C1 C6 C5 180.000(0) . . . . ?
C8 C3 C4 C5 180.000(0) . . . . ?
C9 C5 C6 C1 180.000(0) . . . . ?
N1 C2 C3 C4 180.000(0) . . . . ?
N1 C2 C3 C8 0.000(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 1.120
_oxdiff_exptl_absorpt_empirical_full_min 0.914
####################################################################### 
# 
# 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_tmnb19_vt_37_100_00abs
_database_code_depnum_ccdc_archive 'CCDC 1991870'
loop_
_audit_author_name
_audit_author_address
'Vasyl Kinzhybalo'
;Institute of Low Temperature and Structure Research
Poland
;
_audit_update_record             
;
2020-03-21 deposited with the CCDC.	2021-04-28 downloaded from the CCDC.
;
_audit_creation_date             2019-11-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C, C9 H11 N O2'
_chemical_formula_sum            'C9 H11 N O2'
_chemical_formula_weight         165.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H11 N O2'
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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   16.306(5)
_cell_length_b                   6.980(2)
_cell_length_c                   15.165(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1725.9(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7481
_cell_measurement_temperature    99.9(2)
_cell_measurement_theta_max      29.2640
_cell_measurement_theta_min      2.9750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.1415
-4 0 5 0.1524
4 0 -1 0.1283
-2 0 0 0.2146
2 0 2 0.1698
0 0 -1 0.1102
-2 0 -2 0.1495
6 1 5 0.2164
4 0 -5 0.0938
0 -1 5 0.1252
-2 1 5 0.1585
-4 3 -5 0.2988
-10 -2 -1 0.2319
0 -1 0 0.3356
0 1 0 0.3659

_exptl_crystal_size_max          0.702
_exptl_crystal_size_mid          0.356
_exptl_crystal_size_min          0.246
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
0.0640 0.0203 1.0014 -0.0158 0.0289 0.0335
-3.5785 0.0577 5.2255 -0.1701 0.2291 0.0512
3.8346 0.0234 -1.2199 0.1068 -0.1133 0.0826
-1.9493 -0.0218 0.1092 -0.0455 0.0422 -0.0580
2.0774 0.0624 1.8936 0.0138 0.0157 0.1250
-0.0640 -0.0203 -1.0014 0.0158 -0.0289 -0.0335
-2.0774 -0.0624 -1.8936 -0.0138 -0.0157 -0.1250
6.1044 1.1358 4.5853 0.1338 0.0783 0.3254
3.5785 -0.0577 -5.2255 0.1701 -0.2291 -0.0512
0.3838 -0.8675 5.1011 -0.1556 0.0845 0.1833
-1.6928 1.0485 5.0222 -0.0481 0.2470 0.0932
-4.4097 2.7618 -5.0707 0.2175 0.1202 -0.3314
-9.7473 -2.0876 -1.2686 -0.3487 0.0327 -0.3251
0.0636 -0.9689 0.0940 -0.0765 -0.0602 0.0160
-0.0636 0.9689 -0.0940 0.0765 0.0602 -0.0160

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            25698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.332
_diffrn_reflns_theta_min         2.498
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6249
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     32.00 104.00   1.00    4.00    --   13.60-178.00  90.00   72
  2  ω    -77.00 -32.00   1.00    4.00    --   13.60 178.00   0.00   45
  3  ω    -19.00  92.00   1.00    4.00    --   13.60  57.00  90.00  111
  4  ω    -64.00  46.00   1.00    4.00    --   13.60 -57.00 120.00  110
  5  ω     35.00 106.00   1.00    4.00    --   13.60 178.00 -30.00   71
  6  ω    -19.00  92.00   1.00    4.00    --   13.60  57.00-120.00  111
  7  ω    -50.00  11.00   1.00    4.00    --  -14.38  77.00 -60.00   61
  8  ω    -25.00  30.00   1.00    4.00    --  -14.38 -99.00 -60.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0214048000
_diffrn_orient_matrix_UB_12      0.0784922000
_diffrn_orient_matrix_UB_13      -0.0187552000
_diffrn_orient_matrix_UB_21      -0.0207323000
_diffrn_orient_matrix_UB_22      0.0635318000
_diffrn_orient_matrix_UB_23      0.0289373000
_diffrn_orient_matrix_UB_31      0.0316742000
_diffrn_orient_matrix_UB_32      -0.0113849000
_diffrn_orient_matrix_UB_33      0.0316174000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.891
_reflns_number_gt                3554
_reflns_number_total             4396
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (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         0.260
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.4(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4396
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.056
_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)+(0.0598P)²+0.4107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: CGA(0) CGB(0)
3.a Everything fixed:
 CGA, CGB
3.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C6A(H6A), C4B(H4B), C6B(H6B)
3.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C7B(H7BA,H7BB,
 H7BC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,H9BC)
;
_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
CGA C 0.091760 0.498950 0.106390 0.050 Uiso 0 1 d . . P . .
C1A C 0.0073(3) 0.5114(3) 0.1261(3) 0.0195(8) Uani 1 1 d . . . . .
C2A C 0.0351(3) 0.5067(3) 0.0394(3) 0.0186(8) Uani 1 1 d . . . . .
C3A C 0.1183(3) 0.4951(3) 0.0172(3) 0.0195(9) Uani 1 1 d . . . . .
C4A C 0.1739(3) 0.4892(3) 0.0859(3) 0.0206(8) Uani 1 1 d . . . . .
H4A H 0.230846 0.484768 0.072805 0.025 Uiso 1 1 calc R . . . .
C5A C 0.1494(3) 0.4897(3) 0.1729(3) 0.0189(9) Uani 1 1 d . . . . .
C6A C 0.0658(3) 0.5002(3) 0.1926(3) 0.0189(9) Uani 1 1 d . . . . .
H6A H 0.048725 0.499650 0.252506 0.023 Uiso 1 1 calc R . . . .
C7A C -0.0837(2) 0.5218(4) 0.1507(3) 0.0265(8) Uani 1 1 d . . . . .
H7AA H -0.090330 0.493452 0.213571 0.040 Uiso 1 1 calc GR . . . .
H7AB H -0.114488 0.427857 0.115847 0.040 Uiso 1 1 calc GR . . . .
H7AC H -0.104601 0.650696 0.138316 0.040 Uiso 1 1 calc GR . . . .
C8A C 0.1489(3) 0.4918(4) -0.0774(3) 0.0274(11) Uani 1 1 d . . . . .
H8AA H 0.207326 0.524828 -0.078514 0.041 Uiso 1 1 calc GR . . . .
H8AB H 0.118047 0.585121 -0.112433 0.041 Uiso 1 1 calc GR . . . .
H8AC H 0.141172 0.363415 -0.102127 0.041 Uiso 1 1 calc GR . . . .
C9A C 0.2114(2) 0.4782(4) 0.2466(3) 0.0257(8) Uani 1 1 d . . . . .
H9AA H 0.182819 0.467623 0.303205 0.039 Uiso 1 1 calc GR . . . .
H9AB H 0.245420 0.594016 0.246448 0.039 Uiso 1 1 calc GR . . . .
H9AC H 0.246374 0.365478 0.237968 0.039 Uiso 1 1 calc GR . . . .
N1A N -0.0256(2) 0.5165(3) -0.0315(3) 0.0265(8) Uani 1 1 d . . . . .
O1A O -0.02286(13) 0.3947(3) -0.09041(19) 0.0363(5) Uani 1 1 d . . . . .
O2A O -0.07642(12) 0.6468(3) -0.0306(2) 0.0373(5) Uani 1 1 d . . . . .
CGB C 0.158640 -0.018650 -0.106010 0.050 Uiso 0 1 d . . P . .
C1B C 0.2439(3) -0.0239(3) -0.1279(3) 0.0187(7) Uani 1 1 d . . . . .
C2B C 0.2149(2) -0.0224(4) -0.0413(3) 0.0200(7) Uani 1 1 d . . . . .
C3B C 0.1323(3) -0.0156(3) -0.0162(3) 0.0205(9) Uani 1 1 d . . . . .
C4B C 0.0759(3) -0.0143(3) -0.0858(3) 0.0208(8) Uani 1 1 d . . . . .
H4B H 0.018963 -0.012433 -0.072506 0.025 Uiso 1 1 calc R . . . .
C5B C 0.1004(3) -0.0156(4) -0.1746(3) 0.0199(9) Uani 1 1 d . . . . .
C6B C 0.1838(3) -0.0188(4) -0.1933(3) 0.0192(8) Uani 1 1 d . . . . .
H6B H 0.200646 -0.017355 -0.253227 0.023 Uiso 1 1 calc R . . . .
C7B C 0.3321(3) -0.0254(4) -0.1529(3) 0.0270(8) Uani 1 1 d . . . . .
H7BA H 0.361659 0.070176 -0.117798 0.040 Uiso 1 1 calc GR . . . .
H7BB H 0.337479 0.005452 -0.215638 0.040 Uiso 1 1 calc GR . . . .
H7BC H 0.355135 -0.152677 -0.141616 0.040 Uiso 1 1 calc GR . . . .
C8B C 0.1024(3) -0.0140(4) 0.0768(3) 0.0284(11) Uani 1 1 d . . . . .
H8BA H 0.133829 -0.106691 0.111594 0.043 Uiso 1 1 calc GR . . . .
H8BB H 0.044152 -0.048732 0.078030 0.043 Uiso 1 1 calc GR . . . .
H8BC H 0.109493 0.114406 0.101747 0.043 Uiso 1 1 calc GR . . . .
C9B C 0.0378(2) -0.0120(4) -0.2474(4) 0.0288(9) Uani 1 1 d . . . . .
H9BA H 0.065515 -0.023565 -0.304472 0.043 Uiso 1 1 calc GR . . . .
H9BB H 0.007377 0.109027 -0.245275 0.043 Uiso 1 1 calc GR . . . .
H9BC H -0.000429 -0.119239 -0.239901 0.043 Uiso 1 1 calc GR . . . .
N1B N 0.2767(2) -0.0293(4) 0.0304(2) 0.0258(7) Uani 1 1 d . . . . .
O1B O 0.27382(14) 0.0913(3) 0.0885(2) 0.0384(5) Uani 1 1 d . . . . .
O2B O 0.32806(13) -0.1578(3) 0.0274(2) 0.0412(5) Uani 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
C1A C2A 1.392(6) . ?
C1A C6A 1.391(6) . ?
C1A C7A 1.532(6) . ?
C2A C3A 1.400(6) . ?
C2A N1A 1.464(5) . ?
C3A C4A 1.383(6) . ?
C3A C8A 1.519(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.378(7) . ?
C5A C6A 1.397(6) . ?
C5A C9A 1.510(6) . ?
C6A H6A 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
N1A O1A 1.234(4) . ?
N1A O2A 1.230(3) . ?
C1B C2B 1.396(6) . ?
C1B C6B 1.394(6) . ?
C1B C7B 1.487(6) . ?
C2B C3B 1.401(5) . ?
C2B N1B 1.483(5) . ?
C3B C4B 1.400(7) . ?
C3B C8B 1.492(7) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.404(7) . ?
C5B C6B 1.389(6) . ?
C5B C9B 1.505(6) . ?
C6B H6B 0.9500 . ?
C7B H7BA 0.9800 . ?
C7B H7BB 0.9800 . ?
C7B H7BC 0.9800 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
N1B O1B 1.219(4) . ?
N1B O2B 1.228(3) . ?

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
C2A C1A C7A 123.1(4) . . ?
C6A C1A C2A 117.4(4) . . ?
C6A C1A C7A 119.5(4) . . ?
C1A C2A C3A 123.0(4) . . ?
C1A C2A N1A 118.2(4) . . ?
C3A C2A N1A 118.8(4) . . ?
C2A C3A C8A 123.1(5) . . ?
C4A C3A C2A 117.2(4) . . ?
C4A C3A C8A 119.7(4) . . ?
C3A C4A H4A 119.0 . . ?
C5A C4A C3A 122.1(4) . . ?
C5A C4A H4A 119.0 . . ?
C4A C5A C6A 119.2(5) . . ?
C4A C5A C9A 120.9(4) . . ?
C6A C5A C9A 119.9(4) . . ?
C1A C6A C5A 121.2(4) . . ?
C1A C6A H6A 119.4 . . ?
C5A C6A H6A 119.4 . . ?
C1A C7A H7AA 109.5 . . ?
C1A C7A H7AB 109.5 . . ?
C1A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C3A C8A H8AA 109.5 . . ?
C3A C8A H8AB 109.5 . . ?
C3A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C5A C9A H9AA 109.5 . . ?
C5A C9A H9AB 109.5 . . ?
C5A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
O1A N1A C2A 118.4(3) . . ?
O2A N1A C2A 118.8(3) . . ?
O2A N1A O1A 122.9(4) . . ?
C2B C1B C7B 124.5(4) . . ?
C6B C1B C2B 115.6(4) . . ?
C6B C1B C7B 119.9(4) . . ?
C1B C2B C3B 125.5(4) . . ?
C1B C2B N1B 117.4(4) . . ?
C3B C2B N1B 117.1(4) . . ?
C2B C3B C8B 124.8(5) . . ?
C4B C3B C2B 115.3(4) . . ?
C4B C3B C8B 119.9(4) . . ?
C3B C4B H4B 118.8 . . ?
C3B C4B C5B 122.4(4) . . ?
C5B C4B H4B 118.8 . . ?
C4B C5B C9B 120.7(4) . . ?
C6B C5B C4B 118.3(5) . . ?
C6B C5B C9B 121.0(4) . . ?
C1B C6B H6B 118.6 . . ?
C5B C6B C1B 122.9(4) . . ?
C5B C6B H6B 118.6 . . ?
C1B C7B H7BA 109.5 . . ?
C1B C7B H7BB 109.5 . . ?
C1B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C3B C8B H8BA 109.5 . . ?
C3B C8B H8BB 109.5 . . ?
C3B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C5B C9B H9BA 109.5 . . ?
C5B C9B H9BB 109.5 . . ?
C5B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
O1B N1B C2B 118.8(3) . . ?
O1B N1B O2B 123.9(3) . . ?
O2B N1B C2B 117.4(3) . . ?

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
C6A H6A O1A 0.95 2.53 3.443(6) 161.5 2_565 yes
C7A H7AB O2B 0.98 2.50 3.466(4) 170.7 3_455 yes
C7A H7AC O1B 0.98 2.78 3.685(4) 153.3 3_465 yes
C8A H8AC CGB 0.98 2.68 3.593(3) 154.7 . yes
C6B H6B O1B 0.95 2.55 3.467(6) 161.9 4_554 yes
C7B H7BA O2A 0.98 2.58 3.556(4) 172.2 3_565 yes
C7B H7BC O1A 0.98 2.72 3.625(4) 153.2 3 yes
C8B H8BC CGA 0.98 2.70 3.612(3) 155.0 . 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
C1A C2A C3A C4A -0.3(3) . . . . ?
C1A C2A C3A C8A -179.4(2) . . . . ?
C1A C2A N1A O1A -129.0(3) . . . . ?
C1A C2A N1A O2A 52.0(4) . . . . ?
C2A C1A C6A C5A 1.7(3) . . . . ?
C2A C3A C4A C5A 1.6(3) . . . . ?
C3A C2A N1A O1A 51.7(4) . . . . ?
C3A C2A N1A O2A -127.3(3) . . . . ?
C3A C4A C5A C6A -1.3(3) . . . . ?
C3A C4A C5A C9A 178.5(2) . . . . ?
C4A C5A C6A C1A -0.4(3) . . . . ?
C6A C1A C2A C3A -1.3(3) . . . . ?
C6A C1A C2A N1A 179.41(19) . . . . ?
C7A C1A C2A C3A -179.3(2) . . . . ?
C7A C1A C2A N1A 1.4(3) . . . . ?
C7A C1A C6A C5A 179.7(2) . . . . ?
C8A C3A C4A C5A -179.2(2) . . . . ?
C9A C5A C6A C1A 179.8(2) . . . . ?
N1A C2A C3A C4A 179.0(2) . . . . ?
N1A C2A C3A C8A -0.1(3) . . . . ?
C1B C2B C3B C4B 1.4(4) . . . . ?
C1B C2B C3B C8B -180.0(3) . . . . ?
C1B C2B N1B O1B 127.7(3) . . . . ?
C1B C2B N1B O2B -52.3(4) . . . . ?
C2B C1B C6B C5B -1.0(4) . . . . ?
C2B C3B C4B C5B -1.3(3) . . . . ?
C3B C2B N1B O1B -52.4(4) . . . . ?
C3B C2B N1B O2B 127.5(3) . . . . ?
C3B C4B C5B C6B 0.1(4) . . . . ?
C3B C4B C5B C9B -179.3(2) . . . . ?
C4B C5B C6B C1B 1.1(4) . . . . ?
C6B C1B C2B C3B -0.3(4) . . . . ?
C6B C1B C2B N1B 179.5(2) . . . . ?
C7B C1B C2B C3B 178.1(2) . . . . ?
C7B C1B C2B N1B -2.1(4) . . . . ?
C7B C1B C6B C5B -179.5(2) . . . . ?
C8B C3B C4B C5B 180.0(2) . . . . ?
C9B C5B C6B C1B -179.4(2) . . . . ?
N1B C2B C3B C4B -178.4(2) . . . . ?
N1B C2B C3B C8B 0.2(4) . . . . ?

_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 1.177
_oxdiff_exptl_absorpt_empirical_full_min 0.906
