# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

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

data_lqm-s1-123
_database_code_depnum_ccdc_archive 'CCDC 2078404'
loop_
_audit_author_name
_audit_author_address
'Yan He'
;Henan Normal University
China
;
_audit_update_record             
;
2021-04-19 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_audit_creation_date             2021-04-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N3 O2, H2 O'
_chemical_formula_sum            'C15 H18 N3 O3'
_chemical_formula_weight         288.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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                   19.019(4)
_cell_length_b                   10.378(2)
_cell_length_c                   7.6447(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.068(17)
_cell_angle_gamma                90
_cell_volume                     1485.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2563
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.7920
_cell_measurement_theta_min      4.8840
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             612
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_unetI/netI     0.0703
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5682
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.400
_diffrn_reflns_theta_min         4.723
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00   1.00   1.00    3.35    --  -35.62  92.00 167.00   69
  2  ω     26.00  71.00   1.00    3.35    --   35.62 -92.00  54.00   45
  3  ω    109.00 174.00   1.00   13.41    --  107.12  92.00 167.00   65
  4  ω     49.00  74.00   1.00   13.41    --  107.12 -92.00  54.00   25
  5  ω   -103.00 -16.00   1.00    3.35    --  -35.62 -77.00-120.00   87
  6  ω      7.00 106.00   1.00    3.35    --   35.62  19.00 120.00   99
  7  ω    118.00 170.00   1.00   13.41    --  107.12 111.00 120.00   52
  8  ω     57.00 101.00   1.00   13.41    --  107.12 178.00 -60.00   44
  9  ω    120.00 150.00   1.00   13.41    --  107.12 178.00 -60.00   30
 10  ω    103.00 142.00   1.00   13.41    --  107.12  61.00 150.00   39
 11  ω    127.00 170.00   1.00   13.41    --  107.12  61.00  60.00   43
 12  ω    149.00 174.00   1.00   13.41    --  107.12  61.00 150.00   25
 13  ω     39.00  96.00   1.00   13.41    --  107.12 -95.00  90.00   57
 14  ω     43.00 123.00   1.00   13.41    --  107.12 -45.00  60.00   80
 15  ω     41.00  67.00   1.00   13.41    --  107.12 -95.00 -60.00   26
 16  ω     86.00 176.00   1.00   13.41    --  107.12  30.00 120.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0601384000
_diffrn_orient_matrix_UB_12      0.0489689000
_diffrn_orient_matrix_UB_13      -0.0930581000
_diffrn_orient_matrix_UB_21      -0.0016351000
_diffrn_orient_matrix_UB_22      -0.1269560000
_diffrn_orient_matrix_UB_23      -0.1046102000
_diffrn_orient_matrix_UB_31      -0.0561667000
_diffrn_orient_matrix_UB_32      0.0598262000
_diffrn_orient_matrix_UB_33      -0.1488073000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2084
_reflns_number_total             2859
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.502
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2859
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.1102
_refine_ls_restrained_S_all      1.108
_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)+(0.1889P)²+1.6643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3161
_refine_ls_wR_factor_ref         0.3429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
Uanis(C00K) \\sim Ueq, Uanis(C00L) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
2.a Free rotating group:
 O003(H00O,H00P)
2.b Ternary CH refined with riding coordinates:
 C008(H008), C00B(H00B)
2.c Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00C), C00E(H00D,H00E), C00F(H00F,H00G)
2.d Aromatic/amide H refined with riding coordinates:
 C00G(H00H), C00H(H00I), C00I(H00J), C00J(H00K)
2.e Idealised Me refined as rotating group:
 C00L(H00L,H00M,H00N)
2.f Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.51822(15) 0.3904(3) 0.6431(4) 0.0453(8) Uani 1 1 d . . . . .
O002 O 0.66440(17) 0.7252(3) 0.7905(4) 0.0475(8) Uani 1 1 d . . . . .
H002 H 0.637263 0.746604 0.699673 0.071 Uiso 1 1 calc R U . . .
O003 O 0.54447(16) 0.8172(3) 0.5639(4) 0.0469(8) Uani 1 1 d G . . . .
H00O H 0.524157 0.856733 0.638701 0.070 Uiso 1 1 d G U . . .
H00P H 0.571652 0.868905 0.520939 0.070 Uiso 1 1 d G U . . .
N004 N 0.59589(18) 0.5354(3) 0.7923(4) 0.0409(8) Uani 1 1 d . . . . .
N005 N 0.76521(19) 0.4821(4) 0.6844(5) 0.0511(10) Uani 1 1 d . . . . .
C006 C 0.5753(2) 0.4478(4) 0.6709(4) 0.0369(9) Uani 1 1 d . . . . .
C007 C 0.6672(2) 0.5900(4) 0.8017(5) 0.0384(9) Uani 1 1 d . . . . .
C008 C 0.6935(2) 0.5277(4) 0.6386(5) 0.0405(9) Uani 1 1 d . . . . .
H008 H 0.690704 0.591395 0.543004 0.049 Uiso 1 1 calc R U . . .
C009 C 0.8112(2) 0.4853(5) 0.5586(6) 0.0481(11) Uani 1 1 d . . . . .
N00A N 0.6068(3) 0.3846(5) 0.2385(5) 0.0668(13) Uani 1 1 d . . . . .
C00B C 0.6381(2) 0.4162(4) 0.5790(5) 0.0409(9) Uani 1 1 d . . . . .
H00B H 0.659226 0.334905 0.627892 0.049 Uiso 1 1 calc R U . . .
C00C C 0.6189(2) 0.4021(4) 0.3880(5) 0.0446(10) Uani 1 1 d . . . . .
C00D C 0.7154(3) 0.5555(5) 0.9733(5) 0.0506(11) Uani 1 1 d . . . . .
H00A H 0.690863 0.571835 1.072225 0.061 Uiso 1 1 calc R U . . .
H00C H 0.757917 0.608757 0.988476 0.061 Uiso 1 1 calc R U . . .
C00E C 0.7363(3) 0.4141(5) 0.9717(5) 0.0535(12) Uani 1 1 d . . . . .
H00D H 0.693617 0.361119 0.949177 0.064 Uiso 1 1 calc R U . . .
H00E H 0.763362 0.390281 1.086658 0.064 Uiso 1 1 calc R U . . .
C00F C 0.7810(3) 0.3902(6) 0.8284(6) 0.0584(13) Uani 1 1 d . . . . .
H00F H 0.831190 0.396034 0.880466 0.070 Uiso 1 1 calc R U . . .
H00G H 0.771883 0.303785 0.781763 0.070 Uiso 1 1 calc R U . . .
C00G C 0.8103(3) 0.5904(8) 0.4438(7) 0.0725(18) Uani 1 1 d . . . . .
H00H H 0.777416 0.656458 0.445804 0.087 Uiso 1 1 calc R U . . .
C00H C 0.8616(3) 0.3905(8) 0.5523(9) 0.080(2) Uani 1 1 d . . . . .
H00I H 0.864236 0.320084 0.628336 0.096 Uiso 1 1 calc R U . . .
C00I C 0.8584(3) 0.5962(9) 0.3267(7) 0.088(2) Uani 1 1 d . . . . .
H00J H 0.857010 0.666653 0.251039 0.105 Uiso 1 1 calc R U . . .
C00J C 0.9091(3) 0.4005(9) 0.4302(11) 0.095(3) Uani 1 1 d . . . . .
H00K H 0.942326 0.335321 0.426553 0.114 Uiso 1 1 calc R U . . .
C00K C 0.9078(3) 0.5009(10) 0.3193(9) 0.094(2) Uani 1 1 d . U . . .
C00L C 0.9594(4) 0.5058(13) 0.1866(12) 0.140(4) Uani 1 1 d . U . . .
H00L H 0.948939 0.436278 0.103279 0.210 Uiso 1 1 calc R U . . .
H00M H 1.007533 0.497696 0.249178 0.210 Uiso 1 1 calc R U . . .
H00N H 0.953978 0.586421 0.124229 0.210 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C006 1.224(5) . ?
O002 H002 0.8200 . ?
O002 C007 1.407(5) . ?
O003 H00O 0.8499 . ?
O003 H00P 0.8501 . ?
N004 C006 1.308(5) . ?
N004 C007 1.461(5) . ?
N005 C008 1.427(5) . ?
N005 C009 1.409(5) . ?
N005 C00F 1.448(6) . ?
C006 C00B 1.523(5) . ?
C007 C008 1.562(5) . ?
C007 C00D 1.505(5) . ?
C008 H008 0.9800 . ?
C008 C00B 1.579(6) . ?
C009 C00G 1.398(8) . ?
C009 C00H 1.380(8) . ?
N00A C00C 1.140(6) . ?
C00B H00B 0.9800 . ?
C00B C00C 1.449(5) . ?
C00D H00A 0.9700 . ?
C00D H00C 0.9700 . ?
C00D C00E 1.522(7) . ?
C00E H00D 0.9700 . ?
C00E H00E 0.9700 . ?
C00E C00F 1.519(6) . ?
C00F H00F 0.9700 . ?
C00F H00G 0.9700 . ?
C00G H00H 0.9300 . ?
C00G C00I 1.388(7) . ?
C00H H00I 0.9300 . ?
C00H C00J 1.411(9) . ?
C00I H00J 0.9300 . ?
C00I C00K 1.373(12) . ?
C00J H00K 0.9300 . ?
C00J C00K 1.341(13) . ?
C00K C00L 1.530(8) . ?
C00L H00L 0.9600 . ?
C00L H00M 0.9600 . ?
C00L H00N 0.9600 . ?

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
C007 O002 H002 109.5 . . ?
H00O O003 H00P 109.5 . . ?
C006 N004 C007 117.7(3) . . ?
C008 N005 C00F 117.8(4) . . ?
C009 N005 C008 120.3(3) . . ?
C009 N005 C00F 117.6(4) . . ?
O001 C006 N004 127.4(3) . . ?
O001 C006 C00B 123.9(3) . . ?
N004 C006 C00B 108.4(3) . . ?
O002 C007 N004 111.0(3) . . ?
O002 C007 C008 112.2(3) . . ?
O002 C007 C00D 107.5(3) . . ?
N004 C007 C008 103.0(3) . . ?
N004 C007 C00D 111.6(3) . . ?
C00D C007 C008 111.5(3) . . ?
N005 C008 C007 111.5(3) . . ?
N005 C008 H008 109.4 . . ?
N005 C008 C00B 112.9(4) . . ?
C007 C008 H008 109.4 . . ?
C007 C008 C00B 104.0(3) . . ?
C00B C008 H008 109.4 . . ?
C00G C009 N005 120.4(5) . . ?
C00H C009 N005 121.6(5) . . ?
C00H C009 C00G 117.8(5) . . ?
C006 C00B C008 104.3(3) . . ?
C006 C00B H00B 108.2 . . ?
C008 C00B H00B 108.2 . . ?
C00C C00B C006 114.0(3) . . ?
C00C C00B C008 113.8(3) . . ?
C00C C00B H00B 108.2 . . ?
N00A C00C C00B 175.6(5) . . ?
C007 C00D H00A 109.7 . . ?
C007 C00D H00C 109.7 . . ?
C007 C00D C00E 110.0(4) . . ?
H00A C00D H00C 108.2 . . ?
C00E C00D H00A 109.7 . . ?
C00E C00D H00C 109.7 . . ?
C00D C00E H00D 109.6 . . ?
C00D C00E H00E 109.6 . . ?
C00D C00E C00F 110.1(4) . . ?
H00D C00E H00E 108.2 . . ?
C00F C00E H00D 109.6 . . ?
C00F C00E H00E 109.6 . . ?
N005 C00F C00E 111.9(4) . . ?
N005 C00F H00F 109.2 . . ?
N005 C00F H00G 109.2 . . ?
C00E C00F H00F 109.2 . . ?
C00E C00F H00G 109.2 . . ?
H00F C00F H00G 107.9 . . ?
C009 C00G H00H 120.0 . . ?
C00I C00G C009 120.1(7) . . ?
C00I C00G H00H 120.0 . . ?
C009 C00H H00I 120.0 . . ?
C009 C00H C00J 119.9(8) . . ?
C00J C00H H00I 120.0 . . ?
C00G C00I H00J 119.0 . . ?
C00K C00I C00G 121.9(7) . . ?
C00K C00I H00J 119.0 . . ?
C00H C00J H00K 118.9 . . ?
C00K C00J C00H 122.2(7) . . ?
C00K C00J H00K 118.9 . . ?
C00I C00K C00L 121.8(9) . . ?
C00J C00K C00I 118.1(6) . . ?
C00J C00K C00L 120.2(9) . . ?
C00K C00L H00L 109.5 . . ?
C00K C00L H00M 109.5 . . ?
C00K C00L H00N 109.5 . . ?
H00L C00L H00M 109.5 . . ?
H00L C00L H00N 109.5 . . ?
H00M C00L H00N 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O001 C006 C00B C008 172.3(4) . . . . ?
O001 C006 C00B C00C 47.6(6) . . . . ?
O002 C007 C008 N005 105.6(4) . . . . ?
O002 C007 C008 C00B -132.4(3) . . . . ?
O002 C007 C00D C00E -165.2(4) . . . . ?
N004 C006 C00B C008 -13.7(4) . . . . ?
N004 C006 C00B C00C -138.3(4) . . . . ?
N004 C007 C008 N005 -134.9(4) . . . . ?
N004 C007 C008 C00B -12.9(4) . . . . ?
N004 C007 C00D C00E 72.8(5) . . . . ?
N005 C008 C00B C006 137.1(3) . . . . ?
N005 C008 C00B C00C -98.1(4) . . . . ?
N005 C009 C00G C00I 176.6(5) . . . . ?
N005 C009 C00H C00J -176.8(5) . . . . ?
C006 N004 C007 O002 125.5(4) . . . . ?
C006 N004 C007 C008 5.2(5) . . . . ?
C006 N004 C007 C00D -114.6(4) . . . . ?
C007 N004 C006 O001 179.4(4) . . . . ?
C007 N004 C006 C00B 5.6(5) . . . . ?
C007 C008 C00B C006 16.0(4) . . . . ?
C007 C008 C00B C00C 140.9(4) . . . . ?
C007 C00D C00E C00F 64.9(5) . . . . ?
C008 N005 C009 C00G 39.4(7) . . . . ?
C008 N005 C009 C00H -145.0(5) . . . . ?
C008 N005 C00F C00E -33.7(6) . . . . ?
C008 C007 C00D C00E -41.8(5) . . . . ?
C009 N005 C008 C007 -147.0(4) . . . . ?
C009 N005 C008 C00B 96.3(5) . . . . ?
C009 N005 C00F C00E 169.2(4) . . . . ?
C009 C00G C00I C00K -0.1(9) . . . . ?
C009 C00H C00J C00K 0.8(9) . . . . ?
C00D C007 C008 N005 -15.1(5) . . . . ?
C00D C007 C008 C00B 106.9(4) . . . . ?
C00D C00E C00F N005 -27.0(6) . . . . ?
C00F N005 C008 C007 56.6(5) . . . . ?
C00F N005 C008 C00B -60.1(5) . . . . ?
C00F N005 C009 C00G -164.1(5) . . . . ?
C00F N005 C009 C00H 11.5(7) . . . . ?
C00G C009 C00H C00J -1.1(8) . . . . ?
C00G C00I C00K C00J -0.3(10) . . . . ?
C00G C00I C00K C00L 178.3(6) . . . . ?
C00H C009 C00G C00I 0.8(8) . . . . ?
C00H C00J C00K C00I 0.0(10) . . . . ?
C00H C00J C00K C00L -178.7(6) . . . . ?

_olex2_date_sample_data_collection 2021-04-06
_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 1.847
_oxdiff_exptl_absorpt_empirical_full_min 0.482
####################################################################### 
# 
# 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_lqm-20220325
_database_code_depnum_ccdc_archive 'CCDC 2177447'
loop_
_audit_author_name
_audit_author_address
'Yan He'
;Henan Normal University
China
;
_audit_update_record             
;
2022-06-07 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_audit_creation_date             2022-03-25
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H36 N2 O4'
_chemical_formula_sum            'C24 H36 N2 O4'
_chemical_formula_weight         416.55
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   33.7249(5)
_cell_length_b                   33.7249(5)
_cell_length_c                   8.3001(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     9440.3(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4222
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0010
_cell_measurement_theta_min      5.4610
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.994
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3616
_exptl_crystal_size_max          0.01
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8900
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.365
_diffrn_reflns_theta_min         3.707
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -14.00   1.00    6.53    --  -35.62 149.00 -60.00   89
  2  ω     37.00 129.00   1.00   26.11    --  107.12 -18.00-100.00   92
  3  ω     67.00 110.00   1.00   26.11    --  107.12-149.00-106.00   43
  4  ω    -97.00 -17.00   1.00    6.53    --  -35.62 -38.00  30.00   80
  5  ω      5.00  59.00   1.00    6.53    --   35.62 -99.00-120.00   54
  6  ω     43.00 125.00   1.00   26.11    --  107.12 -61.00 -30.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0056822000
_diffrn_orient_matrix_UB_12      0.0441805000
_diffrn_orient_matrix_UB_13      0.0412361000
_diffrn_orient_matrix_UB_21      0.0451557000
_diffrn_orient_matrix_UB_22      0.0063641000
_diffrn_orient_matrix_UB_23      -0.0100035000
_diffrn_orient_matrix_UB_31      -0.0037946000
_diffrn_orient_matrix_UB_32      0.0097043000
_diffrn_orient_matrix_UB_33      -0.1807373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3507
_reflns_number_total             4404
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.053
_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)+(0.0568P)²+5.5992P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1411
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C12(H12a,H12b), C5(H5a,H5b), C3(H3a,H3b), C4(H4a,H4b)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C15(H15), C18(H18), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C30(H30a,H30b,H30c), C27(H27a,H27b,H27c), C29(H29a,H29b,H29c), C28(H28a,H28b,
 H28c), C26(H26a,H26b,H26c), C25(H25a,H25b,H25c)
;
_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
O7 O 0.31794(3) 0.64275(3) 0.47185(14) 0.0461(3) Uani 1 1 d . . . . .
O11 O 0.37191(4) 0.60423(3) 0.55967(15) 0.0517(3) Uani 1 1 d . . . . .
N8 N 0.38586(4) 0.68682(4) 0.59078(17) 0.0463(3) Uani 1 1 d . . . . .
N1 N 0.28860(4) 0.61798(4) 0.38963(18) 0.0483(4) Uani 1 1 d . . . . .
O22 O 0.43723(5) 0.72787(6) 0.3260(3) 0.1081(8) Uani 1 1 d . . . . .
C9 C 0.38267(5) 0.66806(5) 0.4322(2) 0.0449(4) Uani 1 1 d . . . . .
H9 H 0.369431 0.686764 0.359540 0.054 Uiso 1 1 calc R U . . .
C10 C 0.35727(5) 0.63031(5) 0.4408(2) 0.0447(4) Uani 1 1 d . . . . .
H10 H 0.358080 0.616949 0.336030 0.054 Uiso 1 1 calc R U . . .
C13 C 0.39954(6) 0.65865(6) 0.7125(2) 0.0520(4) Uani 1 1 d . . . . .
H13A H 0.398888 0.671208 0.817636 0.062 Uiso 1 1 calc R U . . .
H13B H 0.426777 0.651283 0.689782 0.062 Uiso 1 1 calc R U . . .
C20 C 0.42413(5) 0.65948(6) 0.3637(2) 0.0506(4) Uani 1 1 d . . . . .
H20 H 0.436677 0.638391 0.426956 0.061 Uiso 1 1 calc R U . . .
C14 C 0.35653(5) 0.71484(5) 0.6321(2) 0.0519(4) Uani 1 1 d . . . . .
C12 C 0.37420(6) 0.62198(6) 0.7156(2) 0.0563(5) Uani 1 1 d . . . . .
H12A H 0.385280 0.603076 0.791307 0.068 Uiso 1 1 calc R U . . .
H12B H 0.347735 0.628827 0.751983 0.068 Uiso 1 1 calc R U . . .
C6 C 0.26213(5) 0.60053(6) 0.5164(2) 0.0541(5) Uani 1 1 d . . . . .
C30 C 0.28618(6) 0.56997(6) 0.6100(3) 0.0637(5) Uani 1 1 d . . . . .
H30A H 0.300399 0.553372 0.535838 0.096 Uiso 1 1 calc R U . . .
H30B H 0.268639 0.553957 0.673734 0.096 Uiso 1 1 calc R U . . .
H30C H 0.304650 0.583320 0.679256 0.096 Uiso 1 1 calc R U . . .
C21 C 0.44982(6) 0.69698(7) 0.3715(3) 0.0639(5) Uani 1 1 d . . . . .
C2 C 0.26973(6) 0.64396(7) 0.2648(3) 0.0644(5) Uani 1 1 d . . . . .
C5 C 0.22928(6) 0.57806(7) 0.4262(3) 0.0711(6) Uani 1 1 d . . . . .
H5A H 0.240956 0.555330 0.372585 0.085 Uiso 1 1 calc R U . . .
H5B H 0.210282 0.568180 0.504200 0.085 Uiso 1 1 calc R U . . .
C19 C 0.34762(7) 0.74500(6) 0.5240(3) 0.0718(6) Uani 1 1 d . . . . .
H19 H 0.360463 0.745984 0.424946 0.086 Uiso 1 1 calc R U . . .
O24 O 0.39580(6) 0.65758(12) 0.1037(2) 0.1660(15) Uani 1 1 d . . . . .
C23 C 0.42243(6) 0.64710(9) 0.1876(3) 0.0770(7) Uani 1 1 d . . . . .
C15 C 0.33746(7) 0.71498(7) 0.7805(3) 0.0711(6) Uani 1 1 d . . . . .
H15 H 0.343413 0.695610 0.856507 0.085 Uiso 1 1 calc R U . . .
C27 C 0.24483(7) 0.63006(7) 0.6373(3) 0.0758(7) Uani 1 1 d . . . . .
H27A H 0.265172 0.648147 0.671203 0.114 Uiso 1 1 calc R U . . .
H27B H 0.234812 0.615972 0.729219 0.114 Uiso 1 1 calc R U . . .
H27C H 0.223654 0.644599 0.587488 0.114 Uiso 1 1 calc R U . . .
C29 C 0.30108(7) 0.65225(9) 0.1362(3) 0.0792(7) Uani 1 1 d . . . . .
H29A H 0.320212 0.670694 0.177600 0.119 Uiso 1 1 calc R U . . .
H29B H 0.288579 0.663319 0.042488 0.119 Uiso 1 1 calc R U . . .
H29C H 0.314125 0.627948 0.107632 0.119 Uiso 1 1 calc R U . . .
C3 C 0.23719(7) 0.61916(9) 0.1842(3) 0.0837(7) Uani 1 1 d . . . . .
H3A H 0.223389 0.635513 0.106061 0.100 Uiso 1 1 calc R U . . .
H3B H 0.249413 0.597345 0.126455 0.100 Uiso 1 1 calc R U . . .
C4 C 0.20745(7) 0.60272(9) 0.3025(4) 0.0889(8) Uani 1 1 d . . . . .
H4A H 0.188166 0.586442 0.246368 0.107 Uiso 1 1 calc R U . . .
H4B H 0.193483 0.624246 0.355219 0.107 Uiso 1 1 calc R U . . .
C18 C 0.31980(8) 0.77354(7) 0.5626(5) 0.0984(10) Uani 1 1 d . . . . .
H18 H 0.314018 0.793471 0.488853 0.118 Uiso 1 1 calc R U . . .
C28 C 0.25390(8) 0.68382(8) 0.3260(4) 0.0909(8) Uani 1 1 d . . . . .
H28A H 0.229205 0.679716 0.381043 0.136 Uiso 1 1 calc R U . . .
H28B H 0.249815 0.701355 0.236373 0.136 Uiso 1 1 calc R U . . .
H28C H 0.272756 0.695364 0.398829 0.136 Uiso 1 1 calc R U . . .
C16 C 0.30973(9) 0.74378(10) 0.8154(4) 0.1015(10) Uani 1 1 d . . . . .
H16 H 0.296946 0.743300 0.914636 0.122 Uiso 1 1 calc R U . . .
C17 C 0.30062(9) 0.77289(9) 0.7081(6) 0.1127(12) Uani 1 1 d . . . . .
H17 H 0.281707 0.792002 0.733026 0.135 Uiso 1 1 calc R U . . .
C26 C 0.49063(8) 0.69265(8) 0.4358(5) 0.1117(12) Uani 1 1 d . . . . .
H26A H 0.505937 0.715664 0.408156 0.168 Uiso 1 1 calc R U . . .
H26B H 0.502776 0.669503 0.390003 0.168 Uiso 1 1 calc R U . . .
H26C H 0.489594 0.689978 0.550886 0.168 Uiso 1 1 calc R U . . .
C25 C 0.45525(10) 0.62326(11) 0.1227(4) 0.1104(11) Uani 1 1 d . . . . .
H25A H 0.479103 0.638791 0.122515 0.166 Uiso 1 1 calc R U . . .
H25B H 0.449086 0.615247 0.014592 0.166 Uiso 1 1 calc R U . . .
H25C H 0.458981 0.600181 0.188689 0.166 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O7 N1 1.4636(18) . ?
O7 C10 1.4148(19) . ?
O11 C10 1.411(2) . ?
O11 C12 1.428(2) . ?
N8 C9 1.465(2) . ?
N8 C13 1.462(2) . ?
N8 C14 1.410(2) . ?
N1 C6 1.500(2) . ?
N1 C2 1.499(3) . ?
O22 C21 1.187(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.536(2) . ?
C9 C20 1.537(2) . ?
C10 H10 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.504(3) . ?
C20 H20 0.9800 . ?
C20 C21 1.534(3) . ?
C20 C23 1.522(3) . ?
C14 C19 1.389(3) . ?
C14 C15 1.390(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C6 C30 1.524(3) . ?
C6 C5 1.537(3) . ?
C6 C27 1.530(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C21 C26 1.484(3) . ?
C2 C29 1.528(3) . ?
C2 C3 1.534(3) . ?
C2 C28 1.533(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C4 1.513(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.382(3) . ?
O24 C23 1.190(3) . ?
C23 C25 1.470(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(4) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.509(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C18 H18 0.9300 . ?
C18 C17 1.370(5) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.361(5) . ?
C17 H17 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C10 O7 N1 112.32(12) . . ?
C10 O11 C12 113.02(13) . . ?
C13 N8 C9 111.34(14) . . ?
C14 N8 C9 117.15(15) . . ?
C14 N8 C13 119.26(15) . . ?
O7 N1 C6 107.42(13) . . ?
O7 N1 C2 106.01(13) . . ?
C2 N1 C6 117.49(14) . . ?
N8 C9 H9 108.0 . . ?
N8 C9 C10 110.91(13) . . ?
N8 C9 C20 110.28(14) . . ?
C10 C9 H9 108.0 . . ?
C10 C9 C20 111.63(15) . . ?
C20 C9 H9 108.0 . . ?
O7 C10 C9 106.59(13) . . ?
O7 C10 H10 108.9 . . ?
O11 C10 O7 112.69(13) . . ?
O11 C10 C9 110.75(14) . . ?
O11 C10 H10 108.9 . . ?
C9 C10 H10 108.9 . . ?
N8 C13 H13A 109.3 . . ?
N8 C13 H13B 109.3 . . ?
N8 C13 C12 111.52(15) . . ?
H13A C13 H13B 108.0 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C9 C20 H20 109.4 . . ?
C21 C20 C9 110.06(16) . . ?
C21 C20 H20 109.4 . . ?
C23 C20 C9 111.88(16) . . ?
C23 C20 H20 109.4 . . ?
C23 C20 C21 106.73(17) . . ?
C19 C14 N8 119.03(18) . . ?
C19 C14 C15 118.0(2) . . ?
C15 C14 N8 122.85(19) . . ?
O11 C12 C13 111.10(15) . . ?
O11 C12 H12A 109.4 . . ?
O11 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N1 C6 C30 107.82(15) . . ?
N1 C6 C5 106.32(16) . . ?
N1 C6 C27 115.57(17) . . ?
C30 C6 C5 107.36(17) . . ?
C30 C6 C27 107.98(18) . . ?
C27 C6 C5 111.45(18) . . ?
C6 C30 H30A 109.5 . . ?
C6 C30 H30B 109.5 . . ?
C6 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O22 C21 C20 120.6(2) . . ?
O22 C21 C26 122.2(2) . . ?
C26 C21 C20 117.26(19) . . ?
N1 C2 C29 107.23(16) . . ?
N1 C2 C3 106.66(18) . . ?
N1 C2 C28 115.6(2) . . ?
C29 C2 C3 106.9(2) . . ?
C29 C2 C28 108.2(2) . . ?
C28 C2 C3 111.9(2) . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C4 C5 C6 114.2(2) . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C14 C19 H19 119.8 . . ?
C18 C19 C14 120.5(3) . . ?
C18 C19 H19 119.8 . . ?
O24 C23 C20 120.6(2) . . ?
O24 C23 C25 121.1(2) . . ?
C25 C23 C20 118.3(2) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(3) . . ?
C16 C15 H15 119.9 . . ?
C6 C27 H27A 109.5 . . ?
C6 C27 H27B 109.5 . . ?
C6 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C2 C29 H29A 109.5 . . ?
C2 C29 H29B 109.5 . . ?
C2 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 C2 113.1(2) . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C3 C4 C5 108.7(2) . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.3 . . ?
C19 C18 H18 119.5 . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 H18 119.5 . . ?
C2 C28 H28A 109.5 . . ?
C2 C28 H28B 109.5 . . ?
C2 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C15 C16 H16 119.2 . . ?
C17 C16 C15 121.6(3) . . ?
C17 C16 H16 119.2 . . ?
C18 C17 H17 120.6 . . ?
C16 C17 C18 118.8(3) . . ?
C16 C17 H17 120.6 . . ?
C21 C26 H26A 109.5 . . ?
C21 C26 H26B 109.5 . . ?
C21 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 N1 C6 C30 -70.51(18) . . . . ?
O7 N1 C6 C5 174.61(15) . . . . ?
O7 N1 C6 C27 50.4(2) . . . . ?
O7 N1 C2 C29 69.1(2) . . . . ?
O7 N1 C2 C3 -176.74(16) . . . . ?
O7 N1 C2 C28 -51.6(2) . . . . ?
N8 C9 C10 O7 68.74(16) . . . . ?
N8 C9 C10 O11 -54.17(17) . . . . ?
N8 C9 C20 C21 -51.01(19) . . . . ?
N8 C9 C20 C23 -169.50(17) . . . . ?
N8 C13 C12 O11 54.6(2) . . . . ?
N8 C14 C19 C18 -178.2(2) . . . . ?
N8 C14 C15 C16 178.3(2) . . . . ?
N1 O7 C10 O11 -94.05(16) . . . . ?
N1 O7 C10 C9 144.26(13) . . . . ?
N1 C6 C5 C4 -53.7(2) . . . . ?
N1 C2 C3 C4 55.8(3) . . . . ?
C9 N8 C13 C12 -53.5(2) . . . . ?
C9 N8 C14 C19 -49.8(2) . . . . ?
C9 N8 C14 C15 133.73(19) . . . . ?
C9 C20 C21 O22 -47.4(3) . . . . ?
C9 C20 C21 C26 133.3(2) . . . . ?
C9 C20 C23 O24 26.3(4) . . . . ?
C9 C20 C23 C25 -156.0(2) . . . . ?
C10 O7 N1 C6 121.08(14) . . . . ?
C10 O7 N1 C2 -112.53(15) . . . . ?
C10 O11 C12 C13 -57.1(2) . . . . ?
C10 C9 C20 C21 -174.78(15) . . . . ?
C10 C9 C20 C23 66.7(2) . . . . ?
C13 N8 C9 C10 52.89(18) . . . . ?
C13 N8 C9 C20 -71.29(18) . . . . ?
C13 N8 C14 C19 171.03(18) . . . . ?
C13 N8 C14 C15 -5.4(3) . . . . ?
C20 C9 C10 O7 -167.85(13) . . . . ?
C20 C9 C10 O11 69.24(17) . . . . ?
C14 N8 C9 C10 -89.30(17) . . . . ?
C14 N8 C9 C20 146.51(15) . . . . ?
C14 N8 C13 C12 87.8(2) . . . . ?
C14 C19 C18 C17 0.4(4) . . . . ?
C14 C15 C16 C17 -0.9(4) . . . . ?
C12 O11 C10 O7 -62.69(18) . . . . ?
C12 O11 C10 C9 56.61(18) . . . . ?
C6 N1 C2 C29 -170.91(18) . . . . ?
C6 N1 C2 C3 -56.7(2) . . . . ?
C6 N1 C2 C28 68.4(2) . . . . ?
C6 C5 C4 C3 56.6(3) . . . . ?
C30 C6 C5 C4 -168.9(2) . . . . ?
C21 C20 C23 O24 -94.1(3) . . . . ?
C21 C20 C23 C25 83.5(3) . . . . ?
C2 N1 C6 C30 170.21(17) . . . . ?
C2 N1 C6 C5 55.3(2) . . . . ?
C2 N1 C6 C27 -68.9(2) . . . . ?
C2 C3 C4 C5 -57.3(3) . . . . ?
C19 C14 C15 C16 1.9(3) . . . . ?
C19 C18 C17 C16 0.7(5) . . . . ?
C23 C20 C21 O22 74.2(3) . . . . ?
C23 C20 C21 C26 -105.1(3) . . . . ?
C15 C14 C19 C18 -1.6(3) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C27 C6 C5 C4 73.0(3) . . . . ?
C29 C2 C3 C4 170.3(2) . . . . ?
C28 C2 C3 C4 -71.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.711
_oxdiff_exptl_absorpt_empirical_full_min 0.685
