# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_tx5389_sq
_database_code_depnum_ccdc_archive 'CCDC 2110020'
loop_
_audit_author_name
_audit_author_address
'Qing Yan'
;Lingnan Normal University
China
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_audit_creation_date             2021-04-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H13 N1.5 O)'
_chemical_formula_sum            'C26 H26 N3 O2'
_chemical_formula_weight         412.50
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   37.4048(8)
_cell_length_b                   4.46170(10)
_cell_length_c                   15.4153(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.692(2)
_cell_angle_gamma                90
_cell_volume                     2555.12(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7961
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      74.3540
_cell_measurement_theta_min      4.7410
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.545
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.072
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16644
_diffrn_reflns_point_group_measured_fraction_full 0.892
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.106
_diffrn_reflns_theta_min         2.379
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -57.00 -30.00   0.50    0.30    --  -47.45 113.00 -69.00   54
  2  ω    -55.00 -26.00   0.50    2.70    --  -99.00  61.00 -30.00   58
  3  ω    -22.00  27.00   0.50    0.30    --  -47.45  19.00 -60.00   98
  4  ω    -55.00 -27.00   0.50    2.70    --  -99.00 125.00-120.00   56
  5  ω    -66.00 -31.00   0.50    2.70    --  -99.00  61.00-150.00   70
  6  ω    -92.00 -62.00   0.50    2.70    --  -99.00 125.00-120.00   60
  7  ω   -107.00 -61.00   0.50    2.70    --  -99.00 113.00 -69.00   92
  8  ω   -102.00 -30.00   0.50    2.70    --  -99.00 125.00  30.00  144
  9  ω    -59.00 -29.00   0.50    2.70    --  -99.00  61.00  60.00   60
 10  ω   -126.00 -80.00   0.50    2.70    --  -99.00 144.00 154.27   92
 11  ω    -24.00  30.00   0.50    0.30    --   47.45 -19.00   0.00  108
 12  ω     37.00  63.00   0.50    2.70    --  103.25 -94.00  60.00   52
 13  ω     74.00 104.00   0.50    2.70    --  103.25 -94.00  60.00   60
 14  ω     54.00 110.00   0.50    2.70    --  103.25-125.00 150.00  112
 15  ω     44.00  71.00   0.50    2.70    --  103.25 -61.00  60.00   54
 16  ω     46.00  98.00   0.50    2.70    --  103.25 -94.00   0.00  104
 17  ω     78.00 105.00   0.50    2.70    --  103.25 -94.00 -60.00   54
 18  ω     67.00 111.00   0.50    2.70    --  103.25-125.00 -90.00   88
 19  ω     64.00  90.00   0.50    2.70    --  103.25-113.00-161.00   52
 20  ω     32.00  74.00   0.50    2.70    --  103.25 -61.00-150.00   84
 21  ω     31.00  74.00   0.50    2.70    --  103.25 -61.00-180.00   86
 22  ω     31.00 109.00   0.50    2.70    --  103.25-125.00-180.00  156
 23  ω     38.00 105.00   0.50    2.70    --  103.25 -94.00 -30.00  134
 24  ω     35.00  62.00   0.50    2.70    --  103.25 -94.00  30.00   54
 25  ω     39.00  65.00   0.50    2.70    --  103.25 -61.00 150.00   52
 26  ω     92.00 168.00   0.50    2.70    --  103.25  30.00   0.00  152
 27  ω    119.00 145.00   0.50    2.70    --  103.25 113.00 -69.00   52
 28  ω     95.00 158.00   0.50    2.70    --  103.25 125.00-120.00  126
 29  ω     91.00 156.00   0.50    2.70    --  103.25  30.00 -30.00  130
 30  ω     91.00 147.00   0.50    2.70    --  103.25  45.00  90.00  112
 31  ω     99.00 165.00   0.50    2.70    --  103.25  61.00 150.00  132
 32  ω     29.00 120.00   0.50    0.30    --   47.45  70.00 -45.80  182
 33  ω      2.00  61.00   0.50    0.30    --   47.45 -57.00-120.00  118
 34  ω     11.00  79.00   0.50    0.30    --   47.45-113.00-161.00  136
 35  ω   -117.00 -92.00   0.50    2.70    --  -99.00-113.00-161.00   50
 36  ω   -114.00 -41.00   0.50    0.30    --  -47.45 -57.00-180.00  146
 37  ω   -119.00 -87.00   0.50    0.30    --  -47.45-125.00-150.00   64
 38  ω   -152.00-113.00   0.50    2.70    --  -99.00 -50.00-130.90   78
 39  ω   -166.00-111.00   0.50    2.70    --  -99.00 -50.00-101.29  110
 40  ω   -167.00 -86.00   0.50    2.70    --  -99.00 -49.00 -88.64  162
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0178383000
_diffrn_orient_matrix_UB_12      -0.0699044000
_diffrn_orient_matrix_UB_13      -0.0828532000
_diffrn_orient_matrix_UB_21      0.0366593000
_diffrn_orient_matrix_UB_22      0.1009651000
_diffrn_orient_matrix_UB_23      0.0468363000
_diffrn_orient_matrix_UB_31      0.0076289000
_diffrn_orient_matrix_UB_32      -0.3226970000
_diffrn_orient_matrix_UB_33      0.0326243000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.547
_reflns_Friedel_fraction_full    0.750
_reflns_Friedel_fraction_max     0.702
_reflns_number_gt                4142
_reflns_number_total             4549
_reflns_odcompleteness_completeness 100.00
_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.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.069
_refine_ls_abs_structure_details 
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.30(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4549
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1347P)²+3.7491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2305
_refine_ls_wR_factor_ref         0.2360
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5) H00A(0.5) H00B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), N00A(H00A,H00B), C12(H12A,H12B), C13(H13A,H13B), C00W(H00C,H00D),
  C00Y(H00E,H00G)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N006(H006), C00F(H00F), C11(H11), C2(H2), C7(H7), C00N(H00N), C5(H5),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C8(H8), C00U(H00U), C00X(H00X), C3(H3),
 C4(H4)
;
_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 0.38368(8) -0.4544(9) 0.1997(2) 0.0454(8) Uani 1 1 d . . . . .
O002 O 0.61485(10) 1.4660(10) 0.3206(2) 0.0534(9) Uani 1 1 d . . . . .
N2 N 0.500000 -0.9731(13) 0.000000 0.0387(11) Uani 1 2 d S T P . .
H2A H 0.489587 -1.090574 -0.042279 0.046 Uiso 0.5 1 calc R U P . .
H2B H 0.510412 -1.090580 0.042278 0.046 Uiso 0.5 1 calc R U P . .
N1 N 0.41281(10) -0.7782(10) 0.0841(3) 0.0442(9) Uani 1 1 d . . . . .
H1 H 0.412943 -0.731961 0.138312 0.053 Uiso 1 1 calc R U . . .
N006 N 0.59003(11) 1.7883(10) 0.4351(3) 0.0465(10) Uani 1 1 d . . . . .
H006 H 0.590019 1.745895 0.380669 0.056 Uiso 1 1 calc R U . . .
N00A N 0.500000 1.9847(16) 0.500000 0.0484(14) Uani 1 2 d S T P . .
H00A H 0.492917 2.101350 0.454380 0.058 Uiso 0.5 1 calc R U P . .
H00B H 0.507084 2.101355 0.545618 0.058 Uiso 0.5 1 calc R U P . .
C00B C 0.66899(12) 1.3463(13) 0.5342(3) 0.0424(11) Uani 1 1 d . . . . .
C00C C 0.64119(12) 1.4611(12) 0.4679(3) 0.0399(10) Uani 1 1 d . . . . .
C10 C 0.36127(11) -0.4677(11) 0.0486(3) 0.0380(10) Uani 1 1 d . . . . .
C1 C 0.33469(11) -0.3523(10) -0.0209(3) 0.0370(9) Uani 1 1 d . . . . .
C00F C 0.61580(11) 1.6737(12) 0.4910(3) 0.0402(10) Uani 1 1 d . . . . .
H00F H 0.617388 1.736002 0.548898 0.048 Uiso 1 1 calc R U . . .
C6 C 0.30752(12) -0.1502(12) 0.0016(3) 0.0423(11) Uani 1 1 d . . . . .
C9 C 0.36065(12) -0.3733(13) 0.1377(3) 0.0445(11) Uani 1 1 d . . . . .
C00I C 0.63951(13) 1.3668(11) 0.3794(3) 0.0430(11) Uani 1 1 d . . . . .
C11 C 0.38788(12) -0.6682(12) 0.0281(3) 0.0399(10) Uani 1 1 d . . . . .
H11 H 0.387559 -0.726189 -0.029933 0.048 Uiso 1 1 calc R U . . .
C00K C 0.69405(12) 1.1423(12) 0.5066(3) 0.0430(11) Uani 1 1 d . . . . .
C2 C 0.33423(13) -0.4198(12) -0.1096(3) 0.0445(11) Uani 1 1 d . . . . .
H2 H 0.351530 -0.550191 -0.126589 0.053 Uiso 1 1 calc R U . . .
C7 C 0.30730(13) -0.0691(13) 0.0913(3) 0.0459(11) Uani 1 1 d . . . . .
H7 H 0.289843 0.063162 0.106490 0.055 Uiso 1 1 calc R U . . .
C00N C 0.66586(14) 1.1578(13) 0.3560(3) 0.0494(12) Uani 1 1 d . . . . .
H00N H 0.665040 1.092603 0.298505 0.059 Uiso 1 1 calc R U . . .
C12 C 0.44105(12) -0.9799(13) 0.0588(4) 0.0458(11) Uani 1 1 d . . . . .
H12A H 0.431447 -1.102056 0.009486 0.055 Uiso 1 1 calc R U . . .
H12B H 0.449178 -1.112214 0.107047 0.055 Uiso 1 1 calc R U . . .
C5 C 0.28197(13) -0.0343(14) -0.0632(3) 0.0495(13) Uani 1 1 d . . . . .
H5 H 0.264377 0.096346 -0.047916 0.059 Uiso 1 1 calc R U . . .
C00Q C 0.69181(13) 1.0551(13) 0.4167(3) 0.0469(11) Uani 1 1 d . . . . .
H00Q H 0.708878 0.922758 0.399549 0.056 Uiso 1 1 calc R U . . .
C00R C 0.67213(14) 1.4313(14) 0.6228(3) 0.0503(13) Uani 1 1 d . . . . .
H00R H 0.655720 1.565802 0.641841 0.060 Uiso 1 1 calc R U . . .
C00S C 0.69895(14) 1.3183(15) 0.6807(3) 0.0525(13) Uani 1 1 d . . . . .
H00S H 0.700904 1.380659 0.738592 0.063 Uiso 1 1 calc R U . . .
C8 C 0.33184(13) -0.1799(13) 0.1549(3) 0.0468(11) Uani 1 1 d . . . . .
H8 H 0.329840 -0.127558 0.212482 0.056 Uiso 1 1 calc R U . . .
C00U C 0.72130(13) 1.0257(13) 0.5687(3) 0.0474(11) Uani 1 1 d . . . . .
H00U H 0.737792 0.889979 0.550592 0.057 Uiso 1 1 calc R U . . .
C13 C 0.47265(12) -0.7930(12) 0.0343(3) 0.0444(11) Uani 1 1 d . . . . .
H13A H 0.463712 -0.645392 -0.009081 0.053 Uiso 1 1 calc R U . . .
H13B H 0.483431 -0.686171 0.085618 0.053 Uiso 1 1 calc R U . . .
C00W C 0.56192(13) 1.9803(13) 0.4596(4) 0.0468(12) Uani 1 1 d . . . . .
H00C H 0.554202 2.117322 0.412265 0.056 Uiso 1 1 calc R U . . .
H00D H 0.570868 2.097552 0.510552 0.056 Uiso 1 1 calc R U . . .
C00X C 0.72401(14) 1.1078(15) 0.6547(4) 0.0549(14) Uani 1 1 d . . . . .
H00X H 0.741840 1.027448 0.695166 0.066 Uiso 1 1 calc R U . . .
C00Y C 0.53024(12) 1.7881(13) 0.4800(4) 0.0466(12) Uani 1 1 d . . . . .
H00E H 0.522338 1.661362 0.430347 0.056 Uiso 1 1 calc R U . . .
H00G H 0.537635 1.659901 0.529714 0.056 Uiso 1 1 calc R U . . .
C3 C 0.30938(14) -0.3017(14) -0.1724(3) 0.0501(12) Uani 1 1 d . . . . .
H3 H 0.310434 -0.348922 -0.230796 0.060 Uiso 1 1 calc R U . . .
C4 C 0.28259(14) -0.1118(14) -0.1496(4) 0.0523(13) Uani 1 1 d . . . . .
H4 H 0.265217 -0.037550 -0.192297 0.063 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.263(6) . ?
O002 C00I 1.293(6) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C13 1.448(6) . ?
N2 C13 1.448(6) 2_655 ?
N1 H1 0.8600 . ?
N1 C11 1.292(6) . ?
N1 C12 1.474(6) . ?
N006 H006 0.8600 . ?
N006 C00F 1.319(6) . ?
N006 C00W 1.441(7) . ?
N00A H00A 0.8900 . ?
N00A H00B 0.8900 . ?
N00A C00Y 1.491(6) . ?
N00A C00Y 1.492(6) 2_656 ?
C00B C00C 1.462(7) . ?
C00B C00K 1.407(7) . ?
C00B C00R 1.410(7) . ?
C00C C00F 1.417(7) . ?
C00C C00I 1.423(7) . ?
C10 C1 1.467(6) . ?
C10 C9 1.438(7) . ?
C10 C11 1.402(7) . ?
C1 C6 1.431(6) . ?
C1 C2 1.399(7) . ?
C00F H00F 0.9300 . ?
C6 C7 1.431(7) . ?
C6 C5 1.399(7) . ?
C9 C8 1.429(7) . ?
C00I C00N 1.433(7) . ?
C11 H11 0.9300 . ?
C00K C00Q 1.433(7) . ?
C00K C00U 1.413(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.355(7) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.347(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.530(7) . ?
C5 H5 0.9300 . ?
C5 C4 1.379(8) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00S 1.359(8) . ?
C00S H00S 0.9300 . ?
C00S C00X 1.417(9) . ?
C8 H8 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C00X 1.369(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C00W H00C 0.9700 . ?
C00W H00D 0.9700 . ?
C00W C00Y 1.525(7) . ?
C00X H00X 0.9300 . ?
C00Y H00E 0.9700 . ?
C00Y H00G 0.9700 . ?
C3 H3 0.9300 . ?
C3 C4 1.388(8) . ?
C4 H4 0.9300 . ?

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
H2A N2 H2B 107.8 . . ?
C13 N2 H2A 109.1 . . ?
C13 N2 H2A 109.1 2_655 . ?
C13 N2 H2B 109.1 2_655 . ?
C13 N2 H2B 109.1 . . ?
C13 N2 C13 112.6(6) . 2_655 ?
C11 N1 H1 118.7 . . ?
C11 N1 C12 122.6(4) . . ?
C12 N1 H1 118.7 . . ?
C00F N006 H006 118.0 . . ?
C00F N006 C00W 124.0(4) . . ?
C00W N006 H006 118.0 . . ?
H00A N00A H00B 108.4 . . ?
C00Y N00A H00A 110.1 2_656 . ?
C00Y N00A H00A 110.1 . . ?
C00Y N00A H00B 110.1 . . ?
C00Y N00A H00B 110.1 2_656 . ?
C00Y N00A C00Y 107.9(6) . 2_656 ?
C00K C00B C00C 117.4(4) . . ?
C00K C00B C00R 118.9(5) . . ?
C00R C00B C00C 123.7(5) . . ?
C00F C00C C00B 120.2(4) . . ?
C00F C00C C00I 118.9(4) . . ?
C00I C00C C00B 121.0(4) . . ?
C9 C10 C1 120.6(4) . . ?
C11 C10 C1 119.9(4) . . ?
C11 C10 C9 119.5(4) . . ?
C6 C1 C10 119.0(4) . . ?
C2 C1 C10 124.6(4) . . ?
C2 C1 C6 116.4(4) . . ?
N006 C00F C00C 123.8(4) . . ?
N006 C00F H00F 118.1 . . ?
C00C C00F H00F 118.1 . . ?
C7 C6 C1 118.5(4) . . ?
C5 C6 C1 120.4(5) . . ?
C5 C6 C7 121.1(5) . . ?
O1 C9 C10 123.6(4) . . ?
O1 C9 C8 119.6(4) . . ?
C8 C9 C10 116.7(4) . . ?
O002 C00I C00C 121.2(5) . . ?
O002 C00I C00N 120.1(4) . . ?
C00C C00I C00N 118.6(4) . . ?
N1 C11 C10 124.6(4) . . ?
N1 C11 H11 117.7 . . ?
C10 C11 H11 117.7 . . ?
C00B C00K C00Q 120.1(5) . . ?
C00B C00K C00U 119.1(5) . . ?
C00U C00K C00Q 120.8(5) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.6(5) . . ?
C3 C2 H2 118.7 . . ?
C6 C7 H7 119.1 . . ?
C8 C7 C6 121.8(5) . . ?
C8 C7 H7 119.1 . . ?
C00I C00N H00N 119.7 . . ?
C00Q C00N C00I 120.5(5) . . ?
C00Q C00N H00N 119.7 . . ?
N1 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
N1 C12 C13 109.3(4) . . ?
H12A C12 H12B 108.3 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.7 . . ?
C00K C00Q H00Q 118.8 . . ?
C00N C00Q C00K 122.4(5) . . ?
C00N C00Q H00Q 118.8 . . ?
C00B C00R H00R 119.7 . . ?
C00S C00R C00B 120.5(5) . . ?
C00S C00R H00R 119.7 . . ?
C00R C00S H00S 119.2 . . ?
C00R C00S C00X 121.5(5) . . ?
C00X C00S H00S 119.2 . . ?
C9 C8 H8 118.4 . . ?
C7 C8 C9 123.2(5) . . ?
C7 C8 H8 118.4 . . ?
C00K C00U H00U 119.2 . . ?
C00X C00U C00K 121.6(5) . . ?
C00X C00U H00U 119.2 . . ?
N2 C13 C12 112.8(4) . . ?
N2 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
N006 C00W H00C 109.8 . . ?
N006 C00W H00D 109.8 . . ?
N006 C00W C00Y 109.2(4) . . ?
H00C C00W H00D 108.3 . . ?
C00Y C00W H00C 109.8 . . ?
C00Y C00W H00D 109.8 . . ?
C00S C00X H00X 120.8 . . ?
C00U C00X C00S 118.3(5) . . ?
C00U C00X H00X 120.8 . . ?
N00A C00Y C00W 109.8(4) . . ?
N00A C00Y H00E 109.7 . . ?
N00A C00Y H00G 109.7 . . ?
C00W C00Y H00E 109.7 . . ?
C00W C00Y H00G 109.7 . . ?
H00E C00Y H00G 108.2 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.4(5) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C9 C8 C7 176.1(5) . . . . ?
O002 C00I C00N C00Q 179.5(5) . . . . ?
N1 C12 C13 N2 -174.0(4) . . . . ?
N006 C00W C00Y N00A -176.4(4) . . . . ?
C00B C00C C00F N006 179.8(5) . . . . ?
C00B C00C C00I O002 179.5(5) . . . . ?
C00B C00C C00I C00N -0.4(7) . . . . ?
C00B C00K C00Q C00N -1.1(8) . . . . ?
C00B C00K C00U C00X -0.4(8) . . . . ?
C00B C00R C00S C00X -1.4(9) . . . . ?
C00C C00B C00K C00Q 0.1(7) . . . . ?
C00C C00B C00K C00U -179.9(5) . . . . ?
C00C C00B C00R C00S -179.2(5) . . . . ?
C00C C00I C00N C00Q -0.5(8) . . . . ?
C10 C1 C6 C7 -0.2(7) . . . . ?
C10 C1 C6 C5 179.5(5) . . . . ?
C10 C1 C2 C3 -178.5(5) . . . . ?
C10 C9 C8 C7 -4.6(8) . . . . ?
C1 C10 C9 O1 -176.9(4) . . . . ?
C1 C10 C9 C8 3.8(7) . . . . ?
C1 C10 C11 N1 178.7(4) . . . . ?
C1 C6 C7 C8 -0.4(8) . . . . ?
C1 C6 C5 C4 -0.2(8) . . . . ?
C1 C2 C3 C4 -1.5(8) . . . . ?
C00F N006 C00W C00Y -89.2(6) . . . . ?
C00F C00C C00I O002 -1.7(7) . . . . ?
C00F C00C C00I C00N 178.3(5) . . . . ?
C6 C1 C2 C3 -0.1(7) . . . . ?
C6 C7 C8 C9 3.0(9) . . . . ?
C6 C5 C4 C3 -1.4(9) . . . . ?
C9 C10 C1 C6 -1.6(6) . . . . ?
C9 C10 C1 C2 176.8(5) . . . . ?
C9 C10 C11 N1 -0.3(7) . . . . ?
C00I C00C C00F N006 1.0(7) . . . . ?
C00I C00N C00Q C00K 1.3(8) . . . . ?
C11 N1 C12 C13 87.7(6) . . . . ?
C11 C10 C1 C6 179.4(4) . . . . ?
C11 C10 C1 C2 -2.3(7) . . . . ?
C11 C10 C9 O1 2.2(7) . . . . ?
C11 C10 C9 C8 -177.1(5) . . . . ?
C00K C00B C00C C00F -178.2(4) . . . . ?
C00K C00B C00C C00I 0.6(7) . . . . ?
C00K C00B C00R C00S 0.1(8) . . . . ?
C00K C00U C00X C00S -0.9(9) . . . . ?
C2 C1 C6 C7 -178.7(5) . . . . ?
C2 C1 C6 C5 1.0(7) . . . . ?
C2 C3 C4 C5 2.3(8) . . . . ?
C7 C6 C5 C4 179.5(5) . . . . ?
C12 N1 C11 C10 -177.7(4) . . . . ?
C5 C6 C7 C8 179.9(5) . . . . ?
C00Q C00K C00U C00X 179.6(5) . . . . ?
C00R C00B C00C C00F 1.1(8) . . . . ?
C00R C00B C00C C00I 179.8(5) . . . . ?
C00R C00B C00K C00Q -179.1(5) . . . . ?
C00R C00B C00K C00U 0.8(7) . . . . ?
C00R C00S C00X C00U 1.9(9) . . . . ?
C00U C00K C00Q C00N 178.9(5) . . . . ?
C13 N2 C13 C12 172.0(5) 2_655 . . . ?
C00W N006 C00F C00C 173.3(5) . . . . ?
C00Y N00A C00Y C00W -179.7(5) 2_656 . . . ?

_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 1.563
_oxdiff_exptl_absorpt_empirical_full_min 0.357
####################################################################### 
# 
# 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_tx5589
_database_code_depnum_ccdc_archive 'CCDC 2110023'
loop_
_audit_author_name
_audit_author_address
'Qing Yan'
;Lingnan Normal University
China
;
_audit_update_record             
;
2021-09-15 deposited with the CCDC.	2022-06-10 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_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         'C11 H10 N2 O4'
_chemical_formula_sum            'C11 H10 N2 O4'
_chemical_formula_weight         234.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8617(5)
_cell_length_b                   6.1503(2)
_cell_length_c                   13.2247(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.683(4)
_cell_angle_gamma                90
_cell_volume                     1031.21(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    169.99(12)
_cell_measurement_theta_max      73.5870
_cell_measurement_theta_min      4.4490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.992
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6462
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.964
_diffrn_reflns_theta_min         4.437
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(12)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  26.00   0.50    0.99    --  -47.45  38.00  30.00   90
  2  ω    -66.00  16.00   0.50    0.99    --  -47.45  93.00 -61.00  164
  3  ω    -59.00 -28.00   0.50    3.95    --  -99.00  61.00 -60.00   62
  4  ω   -102.00 -30.00   0.50    3.95    --  -99.00  93.00 -61.00  144
  5  ω    -76.00 -26.00   0.50    3.95    --  -99.00  77.00 120.00  100
  6  ω    -66.00 -40.00   0.50    3.95    --  -99.00  61.00 150.00   52
  7  ω   -117.00 -82.00   0.50    0.99    --  -47.45-125.00 -90.00   70
  8  ω   -113.00 -87.00   0.50    0.99    --  -47.45-125.00 -60.00   52
  9  ω   -117.00 -77.00   0.50    0.99    --  -47.45-125.00-120.00   80
 10  ω   -127.00-101.00   0.50    3.95    --  -99.00 -93.00-173.00   52
 11  ω    -20.00  65.00   0.50    0.99    --   47.45 -93.00-173.00  170
 12  ω     33.00 101.00   0.50    3.95    --  103.25 -93.00-173.00  136
 13  ω     32.00  74.00   0.50    3.95    --  103.25 -61.00-180.00   84
 14  ω     91.00 167.00   0.50    3.95    --  103.25  45.00 -30.00  152
 15  ω    111.00 145.00   0.50    3.95    --  103.25  93.00 -61.00   68
 16  ω     90.00 136.00   0.50    3.95    --  103.25  61.00-120.00   92
 17  ω     84.00 158.00   0.50    3.95    --  103.25  77.00-120.00  148
 18  ω     49.00  75.00   0.50    3.95    --  103.25 -61.00  60.00   52
 19  ω     36.00  73.00   0.50    3.95    --  103.25 -61.00  30.00   74
 20  ω     42.00  67.00   0.50    3.95    --  103.25 -61.00   0.00   50
 21  ω     33.00  60.00   0.50    3.95    --  103.25 -94.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1094728000
_diffrn_orient_matrix_UB_12      0.1088873000
_diffrn_orient_matrix_UB_13      -0.0192579000
_diffrn_orient_matrix_UB_21      0.0469577000
_diffrn_orient_matrix_UB_22      0.2043336000
_diffrn_orient_matrix_UB_23      0.0577029000
_diffrn_orient_matrix_UB_31      0.0239999000
_diffrn_orient_matrix_UB_32      0.0956263000
_diffrn_orient_matrix_UB_33      -0.1012578000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1669
_reflns_number_total             2017
_reflns_odcompleteness_completeness 99.21
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (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         0.207
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2017
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.072
_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)+(0.0560P)²+0.4017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1214
_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.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C1(H1)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_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 0.38245(10) 1.0186(2) 0.43438(10) 0.0405(3) Uani 1 1 d . . . . .
O3 O 0.25634(12) -0.0395(2) 0.70133(11) 0.0491(4) Uani 1 1 d . . . . .
O4 O 0.50020(11) 0.4719(2) 0.66879(12) 0.0516(4) Uani 1 1 d . . . . .
O2 O 0.15146(10) 0.5201(2) 0.48712(12) 0.0502(4) Uani 1 1 d . . . . .
N2 N 0.38095(12) 0.2089(2) 0.67986(11) 0.0368(4) Uani 1 1 d . . . . .
N1 N 0.20563(12) 0.2338(3) 0.58976(12) 0.0381(4) Uani 1 1 d . . . . .
C6 C 0.33175(13) 0.5138(3) 0.56571(13) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.36487(13) 0.6962(3) 0.52280(13) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.435240 0.728884 0.547080 0.041 Uiso 1 1 calc R U . . .
C4 C 0.31555(13) 0.8488(3) 0.44871(13) 0.0337(4) Uani 1 1 d . . . . .
C7 C 0.22372(14) 0.4294(3) 0.54324(14) 0.0365(4) Uani 1 1 d . . . . .
C3 C 0.22173(14) 0.8798(3) 0.38371(14) 0.0385(4) Uani 1 1 d . . . . .
H3 H 0.162670 0.790437 0.377497 0.046 Uiso 1 1 calc R U . . .
C9 C 0.27951(15) 0.1251(3) 0.65998(14) 0.0372(4) Uani 1 1 d . . . . .
C11 C 0.41089(14) 0.4009(3) 0.64126(14) 0.0368(4) Uani 1 1 d . . . . .
C2 C 0.23141(15) 1.0724(3) 0.32804(14) 0.0399(4) Uani 1 1 d . . . . .
H2 H 0.180461 1.134088 0.278037 0.048 Uiso 1 1 calc R U . . .
C1 C 0.32919(15) 1.1490(3) 0.36178(14) 0.0393(4) Uani 1 1 d . . . . .
H1 H 0.356411 1.275566 0.337997 0.047 Uiso 1 1 calc R U . . .
C8 C 0.09906(16) 0.1414(4) 0.57038(18) 0.0506(5) Uani 1 1 d . . . . .
H8A H 0.070095 0.142552 0.632711 0.076 Uiso 1 1 calc R U . . .
H8B H 0.102124 -0.005475 0.546463 0.076 Uiso 1 1 calc R U . . .
H8C H 0.055163 0.226556 0.519269 0.076 Uiso 1 1 calc R U . . .
C10 C 0.45551(16) 0.0942(4) 0.75812(17) 0.0501(5) Uani 1 1 d . . . . .
H10A H 0.436709 0.118787 0.824424 0.075 Uiso 1 1 calc R U . . .
H10B H 0.525559 0.147627 0.757616 0.075 Uiso 1 1 calc R U . . .
H10C H 0.453042 -0.058772 0.743501 0.075 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.386(2) . ?
O1 C1 1.346(2) . ?
O3 C9 1.211(2) . ?
O4 C11 1.226(2) . ?
O2 C7 1.222(2) . ?
N2 C9 1.386(2) . ?
N2 C11 1.367(2) . ?
N2 C10 1.468(2) . ?
N1 C7 1.389(2) . ?
N1 C9 1.384(2) . ?
N1 C8 1.466(2) . ?
C6 C5 1.358(2) . ?
C6 C7 1.466(2) . ?
C6 C11 1.475(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.426(2) . ?
C4 C3 1.372(2) . ?
C3 H3 0.9300 . ?
C3 C2 1.411(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.347(3) . ?
C1 H1 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C1 O1 C4 107.04(14) . . ?
C9 N2 C10 115.95(15) . . ?
C11 N2 C9 124.43(16) . . ?
C11 N2 C10 119.12(15) . . ?
C7 N1 C8 118.67(16) . . ?
C9 N1 C7 124.65(15) . . ?
C9 N1 C8 116.50(16) . . ?
C5 C6 C7 124.13(16) . . ?
C5 C6 C11 116.29(15) . . ?
C7 C6 C11 119.55(16) . . ?
C6 C5 H5 112.9 . . ?
C6 C5 C4 134.13(16) . . ?
C4 C5 H5 112.9 . . ?
O1 C4 C5 112.03(14) . . ?
C3 C4 O1 108.08(16) . . ?
C3 C4 C5 139.87(17) . . ?
O2 C7 N1 119.85(16) . . ?
O2 C7 C6 124.01(17) . . ?
N1 C7 C6 116.14(16) . . ?
C4 C3 H3 126.3 . . ?
C4 C3 C2 107.34(16) . . ?
C2 C3 H3 126.3 . . ?
O3 C9 N2 121.35(18) . . ?
O3 C9 N1 120.89(17) . . ?
N1 C9 N2 117.75(16) . . ?
O4 C11 N2 120.37(17) . . ?
O4 C11 C6 122.62(17) . . ?
N2 C11 C6 117.00(15) . . ?
C3 C2 H2 126.9 . . ?
C1 C2 C3 106.26(16) . . ?
C1 C2 H2 126.9 . . ?
O1 C1 C2 111.28(17) . . ?
O1 C1 H1 124.4 . . ?
C2 C1 H1 124.4 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C3 C2 0.2(2) . . . . ?
C6 C5 C4 O1 176.40(19) . . . . ?
C6 C5 C4 C3 -5.7(4) . . . . ?
C5 C6 C7 O2 -3.4(3) . . . . ?
C5 C6 C7 N1 176.37(16) . . . . ?
C5 C6 C11 O4 3.9(3) . . . . ?
C5 C6 C11 N2 -175.58(16) . . . . ?
C5 C4 C3 C2 -177.8(2) . . . . ?
C4 O1 C1 C2 -0.2(2) . . . . ?
C4 C3 C2 C1 -0.3(2) . . . . ?
C7 N1 C9 O3 176.21(17) . . . . ?
C7 N1 C9 N2 -4.9(3) . . . . ?
C7 C6 C5 C4 -1.8(3) . . . . ?
C7 C6 C11 O4 -174.60(18) . . . . ?
C7 C6 C11 N2 5.9(2) . . . . ?
C3 C2 C1 O1 0.3(2) . . . . ?
C9 N2 C11 O4 174.35(18) . . . . ?
C9 N2 C11 C6 -6.2(3) . . . . ?
C9 N1 C7 O2 -175.32(17) . . . . ?
C9 N1 C7 C6 4.9(3) . . . . ?
C11 N2 C9 O3 -175.51(17) . . . . ?
C11 N2 C9 N1 5.6(3) . . . . ?
C11 C6 C5 C4 179.80(18) . . . . ?
C11 C6 C7 O2 174.92(18) . . . . ?
C11 C6 C7 N1 -5.3(2) . . . . ?
C1 O1 C4 C5 178.56(15) . . . . ?
C1 O1 C4 C3 -0.03(19) . . . . ?
C8 N1 C7 O2 -0.3(3) . . . . ?
C8 N1 C7 C6 179.88(16) . . . . ?
C8 N1 C9 O3 1.1(3) . . . . ?
C8 N1 C9 N2 -179.97(16) . . . . ?
C10 N2 C9 O3 -3.7(3) . . . . ?
C10 N2 C9 N1 177.38(16) . . . . ?
C10 N2 C11 O4 2.8(3) . . . . ?
C10 N2 C11 C6 -177.75(16) . . . . ?

_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 3.185
_oxdiff_exptl_absorpt_empirical_full_min 0.640
