# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_zz31cult
_audit_block_doi                 10.5517/ccdc.csd.cc2pmf81
_database_code_depnum_ccdc_archive 'CCDC 2491323'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2017-08-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H13 N O2'
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   27.5910(10)
_cell_length_b                   8.5988(4)
_cell_length_c                   12.4000(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.846(4)
_cell_angle_gamma                90
_cell_volume                     2889.4(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3419
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.7970
_cell_measurement_theta_min      4.8830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.692
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless

_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9020
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.497
_diffrn_reflns_theta_min         4.896
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     58.00 133.00   1.00    2.00    --  110.57 -30.00  60.00   75
  2  ω     19.00  71.00   1.00    1.00    --   40.45 -99.00 150.00   52
  3  ω    -78.00 -17.00   1.00    1.00    --  -40.45 125.00 -90.00   61
  4  ω   -104.00   0.00   1.00    1.00    --  -40.45 -19.00  90.00  104
  5  ω     53.00 122.00   1.00    2.00    --  110.57-125.00-120.00   69
  6  ω     45.00 122.00   1.00    2.00    --  110.57 -61.00-120.00   77
  7  ω     97.00 178.00   1.00    2.00    --  110.57 125.00-120.00   81
  8  ω     46.00 133.00   1.00    2.00    --  110.57 -30.00 150.00   87
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0096578000
_diffrn_orient_matrix_UB_12      0.1720534000
_diffrn_orient_matrix_UB_13      0.0239505000
_diffrn_orient_matrix_UB_21      0.0271451000
_diffrn_orient_matrix_UB_22      0.0502642000
_diffrn_orient_matrix_UB_23      -0.0920767000
_diffrn_orient_matrix_UB_31      -0.0489912000
_diffrn_orient_matrix_UB_32      -0.0058055000
_diffrn_orient_matrix_UB_33      -0.0831832000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4227
_reflns_number_total             5141
_reflns_odcompleteness_completeness 98.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         5141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.012
_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)+(0.0780P)²+0.0110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1333
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11), C23(H23),
 C24(H24), C25(H25), C26(H26), C2A(H2A), C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A),
  C9A(H9A), C10A(H10A), C11A(H11A), C23A(H23A), C24A(H24A), C25A(H25A),
 C26A(H26A)
2.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O1A(H1A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.44959(4) 0.02269(15) 0.07892(11) 0.0331(3) Uani 1 1 d . . . . .
H1 H 0.4652 -0.0446 0.0502 0.050 Uiso 1 1 calc GR . . . .
O2 O 0.49577(5) 0.18553(16) 0.00065(11) 0.0360(3) Uani 1 1 d . . . . .
N1 N 0.37259(5) 0.15836(18) 0.15704(12) 0.0264(3) Uani 1 1 d . . . . .
C1 C 0.33722(5) 0.1284(2) 0.06384(14) 0.0257(4) Uani 1 1 d . . . . .
C2 C 0.32584(6) 0.2147(2) -0.03249(14) 0.0300(4) Uani 1 1 d . . . . .
H2 H 0.3435 0.3066 -0.0429 0.036 Uiso 1 1 calc R . . . .
C3 C 0.28766(6) 0.1612(2) -0.11260(15) 0.0319(4) Uani 1 1 d . . . . .
H3 H 0.2791 0.2174 -0.1794 0.038 Uiso 1 1 calc R . . . .
C4 C 0.26144(6) 0.0270(2) -0.09785(15) 0.0326(4) Uani 1 1 d . . . . .
H4 H 0.2355 -0.0068 -0.1545 0.039 Uiso 1 1 calc R . . . .
C5 C 0.27286(6) -0.0580(2) -0.00119(15) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.2548 -0.1495 0.0085 0.037 Uiso 1 1 calc R . . . .
C6 C 0.31124(6) -0.0073(2) 0.08177(15) 0.0270(4) Uani 1 1 d . . . . .
C7 C 0.33181(6) -0.0614(2) 0.19103(15) 0.0273(4) Uani 1 1 d . . . . .
C8 C 0.32105(6) -0.1834(2) 0.25610(15) 0.0310(4) Uani 1 1 d . . . . .
H8 H 0.2954 -0.2546 0.2287 0.037 Uiso 1 1 calc R . . . .
C9 C 0.34819(6) -0.1999(2) 0.36125(16) 0.0329(4) Uani 1 1 d . . . . .
H9 H 0.3411 -0.2832 0.4061 0.039 Uiso 1 1 calc R . . . .
C10 C 0.38611(6) -0.0950(2) 0.40221(15) 0.0307(4) Uani 1 1 d . . . . .
H10 H 0.4044 -0.1088 0.4746 0.037 Uiso 1 1 calc R . . . .
C11 C 0.39758(6) 0.0284(2) 0.33956(14) 0.0287(4) Uani 1 1 d . . . . .
H11 H 0.4235 0.0989 0.3672 0.034 Uiso 1 1 calc R . . . .
C12 C 0.36955(5) 0.0446(2) 0.23450(14) 0.0258(4) Uani 1 1 d . . . . .
C20 C 0.46567(6) 0.1616(2) 0.06002(14) 0.0268(4) Uani 1 1 d . . . . .
C21 C 0.44717(5) 0.2926(2) 0.11987(13) 0.0256(4) Uani 1 1 d . . . . .
C22 C 0.40540(5) 0.2884(2) 0.16922(13) 0.0261(4) Uani 1 1 d . . . . .
C23 C 0.39391(6) 0.4159(2) 0.22781(15) 0.0330(4) Uani 1 1 d . . . . .
H23 H 0.3657 0.4127 0.2616 0.040 Uiso 1 1 calc R . . . .
C24 C 0.42318(7) 0.5485(2) 0.23774(16) 0.0350(4) Uani 1 1 d . . . . .
H24 H 0.4151 0.6351 0.2786 0.042 Uiso 1 1 calc R . . . .
C25 C 0.46407(6) 0.5545(2) 0.18815(15) 0.0312(4) Uani 1 1 d . . . . .
H25 H 0.4840 0.6454 0.1941 0.037 Uiso 1 1 calc R . . . .
C26 C 0.47576(6) 0.4276(2) 0.13003(14) 0.0285(4) Uani 1 1 d . . . . .
H26 H 0.5039 0.4322 0.0962 0.034 Uiso 1 1 calc R . . . .
O1A O 0.04272(4) 0.38703(15) 0.09575(10) 0.0301(3) Uani 1 1 d . . . . .
H1A H 0.0285 0.3953 0.0299 0.045 Uiso 1 1 calc GR . . . .
O2A O 0.00210(4) 0.60775(15) 0.11057(10) 0.0312(3) Uani 1 1 d . . . . .
N1A N 0.12335(5) 0.33720(18) 0.25565(11) 0.0264(3) Uani 1 1 d . . . . .
C1A C 0.15332(5) 0.4043(2) 0.18938(13) 0.0250(4) Uani 1 1 d . . . . .
C2A C 0.15401(6) 0.5555(2) 0.15240(15) 0.0299(4) Uani 1 1 d . . . . .
H2A H 0.1310 0.6303 0.1683 0.036 Uiso 1 1 calc R . . . .
C3A C 0.18943(6) 0.5943(2) 0.09130(16) 0.0337(4) Uani 1 1 d . . . . .
H3A H 0.1911 0.6982 0.0662 0.040 Uiso 1 1 calc R . . . .
C4A C 0.22277(6) 0.4837(3) 0.06577(16) 0.0357(4) Uani 1 1 d . . . . .
H4A H 0.2466 0.5133 0.0235 0.043 Uiso 1 1 calc R . . . .
C5A C 0.22137(6) 0.3324(2) 0.10132(14) 0.0320(4) Uani 1 1 d . . . . .
H5A H 0.2436 0.2571 0.0827 0.038 Uiso 1 1 calc R . . . .
C6A C 0.18672(5) 0.2910(2) 0.16520(14) 0.0268(4) Uani 1 1 d . . . . .
C7A C 0.17659(6) 0.1494(2) 0.21989(14) 0.0281(4) Uani 1 1 d . . . . .
C8A C 0.19728(6) 0.0018(2) 0.22857(15) 0.0325(4) Uani 1 1 d . . . . .
H8A H 0.2245 -0.0216 0.1944 0.039 Uiso 1 1 calc R . . . .
C9A C 0.17782(7) -0.1107(2) 0.28764(16) 0.0344(4) Uani 1 1 d . . . . .
H9A H 0.1922 -0.2114 0.2954 0.041 Uiso 1 1 calc R . . . .
C10A C 0.13699(7) -0.0775(2) 0.33637(16) 0.0356(4) Uani 1 1 d . . . . .
H10A H 0.1233 -0.1578 0.3738 0.043 Uiso 1 1 calc R . . . .
C11A C 0.11635(6) 0.0687(2) 0.33115(15) 0.0315(4) Uani 1 1 d . . . . .
H11A H 0.0890 0.0911 0.3650 0.038 Uiso 1 1 calc R . . . .
C12A C 0.13721(6) 0.1824(2) 0.27427(14) 0.0261(4) Uani 1 1 d . . . . .
C20A C 0.03084(5) 0.5049(2) 0.15174(14) 0.0250(4) Uani 1 1 d . . . . .
C21A C 0.05249(6) 0.5069(2) 0.27059(14) 0.0267(4) Uani 1 1 d . . . . .
C22A C 0.09462(6) 0.4222(2) 0.31898(14) 0.0262(4) Uani 1 1 d . . . . .
C23A C 0.11046(6) 0.4267(2) 0.43241(15) 0.0334(4) Uani 1 1 d . . . . .
H23A H 0.1390 0.3698 0.4651 0.040 Uiso 1 1 calc R . . . .
C24A C 0.08525(7) 0.5131(2) 0.49806(16) 0.0366(4) Uani 1 1 d . . . . .
H24A H 0.0960 0.5135 0.5755 0.044 Uiso 1 1 calc R . . . .
C25A C 0.04427(6) 0.5990(2) 0.45071(15) 0.0347(4) Uani 1 1 d . . . . .
H25A H 0.0272 0.6595 0.4956 0.042 Uiso 1 1 calc R . . . .
C26A C 0.02831(6) 0.5967(2) 0.33865(15) 0.0300(4) Uani 1 1 d . . . . .
H26A H 0.0004 0.6570 0.3069 0.036 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C20 1.310(2) . ?
O2 C20 1.227(2) . ?
N1 C1 1.389(2) . ?
N1 C12 1.384(2) . ?
N1 C22 1.428(2) . ?
C1 C2 1.391(3) . ?
C1 C6 1.409(2) . ?
C2 C3 1.384(2) . ?
C3 C4 1.392(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.400(2) . ?
C6 C7 1.444(3) . ?
C7 C8 1.389(3) . ?
C7 C12 1.412(2) . ?
C8 C9 1.383(3) . ?
C9 C10 1.402(3) . ?
C10 C11 1.387(3) . ?
C11 C12 1.391(3) . ?
C20 C21 1.491(2) . ?
C21 C22 1.403(2) . ?
C21 C26 1.396(2) . ?
C22 C23 1.385(3) . ?
C23 C24 1.389(3) . ?
C24 C25 1.384(2) . ?
C25 C26 1.378(3) . ?
O1A C20A 1.305(2) . ?
O2A C20A 1.232(2) . ?
N1A C1A 1.396(2) . ?
N1A C12A 1.392(2) . ?
N1A C22A 1.419(2) . ?
C1A C2A 1.380(3) . ?
C1A C6A 1.411(2) . ?
C2A C3A 1.385(2) . ?
C3A C4A 1.401(3) . ?
C4A C5A 1.376(3) . ?
C5A C6A 1.397(2) . ?
C6A C7A 1.447(3) . ?
C7A C8A 1.387(3) . ?
C7A C12A 1.411(2) . ?
C8A C9A 1.381(3) . ?
C9A C10A 1.404(3) . ?
C10A C11A 1.376(3) . ?
C11A C12A 1.392(3) . ?
C20A C21A 1.482(2) . ?
C21A C22A 1.407(2) . ?
C21A C26A 1.402(2) . ?
C22A C23A 1.393(3) . ?
C23A C24A 1.382(3) . ?
C24A C25A 1.385(3) . ?
C25A C26A 1.377(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
C1 N1 C22 124.39(15) . . ?
C12 N1 C1 108.76(14) . . ?
C12 N1 C22 126.83(14) . . ?
N1 C1 C2 128.71(16) . . ?
N1 C1 C6 108.71(15) . . ?
C2 C1 C6 122.55(16) . . ?
C3 C2 C1 117.21(17) . . ?
C2 C3 C4 121.72(17) . . ?
C5 C4 C3 120.71(17) . . ?
C4 C5 C6 119.18(17) . . ?
C1 C6 C7 107.03(15) . . ?
C5 C6 C1 118.63(17) . . ?
C5 C6 C7 134.32(17) . . ?
C8 C7 C6 134.34(17) . . ?
C8 C7 C12 119.24(16) . . ?
C12 C7 C6 106.38(16) . . ?
C9 C8 C7 119.23(17) . . ?
C8 C9 C10 120.64(18) . . ?
C11 C10 C9 121.54(17) . . ?
C10 C11 C12 117.12(16) . . ?
N1 C12 C7 109.13(15) . . ?
N1 C12 C11 128.67(16) . . ?
C11 C12 C7 122.20(17) . . ?
O1 C20 C21 116.14(14) . . ?
O2 C20 O1 123.43(17) . . ?
O2 C20 C21 120.36(16) . . ?
C22 C21 C20 125.68(16) . . ?
C26 C21 C20 115.65(14) . . ?
C26 C21 C22 118.61(16) . . ?
C21 C22 N1 122.04(16) . . ?
C23 C22 N1 118.18(14) . . ?
C23 C22 C21 119.72(16) . . ?
C22 C23 C24 120.66(16) . . ?
C25 C24 C23 119.99(18) . . ?
C26 C25 C24 119.59(17) . . ?
C25 C26 C21 121.41(15) . . ?
C1A N1A C22A 124.58(15) . . ?
C12A N1A C1A 108.56(14) . . ?
C12A N1A C22A 124.42(15) . . ?
N1A C1A C6A 108.82(15) . . ?
C2A C1A N1A 129.21(16) . . ?
C2A C1A C6A 121.94(15) . . ?
C1A C2A C3A 117.65(17) . . ?
C2A C3A C4A 121.40(18) . . ?
C5A C4A C3A 120.69(17) . . ?
C4A C5A C6A 119.04(17) . . ?
C1A C6A C7A 106.86(14) . . ?
C5A C6A C1A 119.25(18) . . ?
C5A C6A C7A 133.86(17) . . ?
C8A C7A C6A 133.91(16) . . ?
C8A C7A C12A 119.32(17) . . ?
C12A C7A C6A 106.76(15) . . ?
C9A C8A C7A 119.10(16) . . ?
C8A C9A C10A 120.60(18) . . ?
C11A C10A C9A 121.59(18) . . ?
C10A C11A C12A 117.28(16) . . ?
N1A C12A C7A 109.00(15) . . ?
C11A C12A N1A 128.96(15) . . ?
C11A C12A C7A 121.98(17) . . ?
O1A C20A C21A 116.30(15) . . ?
O2A C20A O1A 122.92(16) . . ?
O2A C20A C21A 120.75(16) . . ?
C22A C21A C20A 124.35(16) . . ?
C26A C21A C20A 117.15(15) . . ?
C26A C21A C22A 118.49(16) . . ?
C21A C22A N1A 122.23(15) . . ?
C23A C22A N1A 118.15(15) . . ?
C23A C22A C21A 119.54(16) . . ?
C24A C23A C22A 120.87(16) . . ?
C23A C24A C25A 119.85(18) . . ?
C26A C25A C24A 120.05(17) . . ?
C25A C26A C21A 121.16(16) . . ?

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 C20 C21 C22 -18.3(2) . . . . ?
O1 C20 C21 C26 159.04(15) . . . . ?
O2 C20 C21 C22 164.60(16) . . . . ?
O2 C20 C21 C26 -18.1(2) . . . . ?
N1 C1 C2 C3 -178.25(16) . . . . ?
N1 C1 C6 C5 178.74(14) . . . . ?
N1 C1 C6 C7 0.21(18) . . . . ?
N1 C22 C23 C24 -176.85(17) . . . . ?
C1 N1 C12 C7 0.26(18) . . . . ?
C1 N1 C12 C11 -179.83(16) . . . . ?
C1 N1 C22 C21 -77.5(2) . . . . ?
C1 N1 C22 C23 99.7(2) . . . . ?
C1 C2 C3 C4 0.2(2) . . . . ?
C1 C6 C7 C8 177.37(18) . . . . ?
C1 C6 C7 C12 -0.05(18) . . . . ?
C2 C1 C6 C5 0.7(2) . . . . ?
C2 C1 C6 C7 -177.81(15) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 177.68(18) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C12 -178.25(18) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
C6 C7 C8 C9 -178.37(18) . . . . ?
C6 C7 C12 N1 -0.12(18) . . . . ?
C6 C7 C12 C11 179.96(15) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C7 C12 N1 -178.01(14) . . . . ?
C8 C7 C12 C11 2.1(2) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 N1 178.38(15) . . . . ?
C10 C11 C12 C7 -1.7(2) . . . . ?
C12 N1 C1 C2 177.57(16) . . . . ?
C12 N1 C1 C6 -0.29(18) . . . . ?
C12 N1 C22 C21 104.1(2) . . . . ?
C12 N1 C22 C23 -78.8(2) . . . . ?
C12 C7 C8 C9 -1.2(2) . . . . ?
C20 C21 C22 N1 -6.6(3) . . . . ?
C20 C21 C22 C23 176.30(16) . . . . ?
C20 C21 C26 C25 -176.76(16) . . . . ?
C21 C22 C23 C24 0.4(3) . . . . ?
C22 N1 C1 C2 -1.1(3) . . . . ?
C22 N1 C1 C6 -178.97(14) . . . . ?
C22 N1 C12 C7 178.90(14) . . . . ?
C22 N1 C12 C11 -1.2(3) . . . . ?
C22 C21 C26 C25 0.8(3) . . . . ?
C22 C23 C24 C25 0.5(3) . . . . ?
C23 C24 C25 C26 -0.7(3) . . . . ?
C24 C25 C26 C21 0.0(3) . . . . ?
C26 C21 C22 N1 176.13(15) . . . . ?
C26 C21 C22 C23 -1.0(2) . . . . ?
O1A C20A C21A C22A 20.0(2) . . . . ?
O1A C20A C21A C26A -158.38(15) . . . . ?
O2A C20A C21A C22A -162.11(16) . . . . ?
O2A C20A C21A C26A 19.5(2) . . . . ?
N1A C1A C2A C3A 176.90(16) . . . . ?
N1A C1A C6A C5A -178.70(14) . . . . ?
N1A C1A C6A C7A -0.30(18) . . . . ?
N1A C22A C23A C24A 177.16(18) . . . . ?
C1A N1A C12A C7A 0.21(18) . . . . ?
C1A N1A C12A C11A -176.75(17) . . . . ?
C1A N1A C22A C21A 70.3(2) . . . . ?
C1A N1A C22A C23A -106.6(2) . . . . ?
C1A C2A C3A C4A 1.3(3) . . . . ?
C1A C6A C7A C8A -178.59(18) . . . . ?
C1A C6A C7A C12A 0.42(18) . . . . ?
C2A C1A C6A C5A -0.5(2) . . . . ?
C2A C1A C6A C7A 177.95(15) . . . . ?
C2A C3A C4A C5A -0.3(3) . . . . ?
C3A C4A C5A C6A -1.2(3) . . . . ?
C4A C5A C6A C1A 1.5(2) . . . . ?
C4A C5A C6A C7A -176.35(18) . . . . ?
C5A C6A C7A C8A -0.5(3) . . . . ?
C5A C6A C7A C12A 178.48(18) . . . . ?
C6A C1A C2A C3A -1.0(3) . . . . ?
C6A C7A C8A C9A -179.16(18) . . . . ?
C6A C7A C12A N1A -0.39(18) . . . . ?
C6A C7A C12A C11A 176.82(15) . . . . ?
C7A C8A C9A C10A 1.3(3) . . . . ?
C8A C7A C12A N1A 178.79(15) . . . . ?
C8A C7A C12A C11A -4.0(3) . . . . ?
C8A C9A C10A C11A -2.8(3) . . . . ?
C9A C10A C11A C12A 0.8(3) . . . . ?
C10A C11A C12A N1A 179.20(17) . . . . ?
C10A C11A C12A C7A 2.6(3) . . . . ?
C12A N1A C1A C2A -178.02(17) . . . . ?
C12A N1A C1A C6A 0.06(18) . . . . ?
C12A N1A C22A C21A -129.46(18) . . . . ?
C12A N1A C22A C23A 53.6(2) . . . . ?
C12A C7A C8A C9A 1.9(3) . . . . ?
C20A C21A C22A N1A 6.2(3) . . . . ?
C20A C21A C22A C23A -176.96(17) . . . . ?
C20A C21A C26A C25A 176.59(17) . . . . ?
C21A C22A C23A C24A 0.2(3) . . . . ?
C22A N1A C1A C2A -15.1(3) . . . . ?
C22A N1A C1A C6A 162.93(14) . . . . ?
C22A N1A C12A C7A -162.70(14) . . . . ?
C22A N1A C12A C11A 20.3(3) . . . . ?
C22A C21A C26A C25A -1.9(3) . . . . ?
C22A C23A C24A C25A -1.3(3) . . . . ?
C23A C24A C25A C26A 0.9(3) . . . . ?
C24A C25A C26A C21A 0.8(3) . . . . ?
C26A C21A C22A N1A -175.44(16) . . . . ?
C26A C21A C22A C23A 1.4(3) . . . . ?

_olex2_date_sample_data_collection 2017-05-25
_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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_exp_3513
_audit_block_doi                 10.5517/ccdc.csd.cc2pmf92
_database_code_depnum_ccdc_archive 'CCDC 2491324'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2017-02-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H13 N O2'
_chemical_formula_sum            'C19 H13 N O2'
_chemical_formula_weight         287.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   27.509(3)
_cell_length_b                   8.6819(10)
_cell_length_c                   12.636(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.062(12)
_cell_angle_gamma                90
_cell_volume                     2961.7(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3542
_cell_measurement_temperature    173.11(10)
_cell_measurement_theta_max      24.7160
_cell_measurement_theta_min      3.3230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50578
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0809
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20561
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.018
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173.11(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  34.00   1.00    4.00    --   16.81 -57.00 -90.00   86
  2  ω      4.00  65.00   1.00    4.00    --   16.81-133.00 -93.00   61
  3  ω    -25.00  23.00   1.00    4.00    --  -17.59 -99.00 -60.00   48
  4  ω    -25.00   2.00   1.00    4.00    --  -17.59 -99.00  60.00   27
  5  ω    -22.00  23.00   1.00    4.00    --  -17.59 -99.00  90.00   45
  6  ω     26.00  77.00   1.00    4.00    --   16.81-136.00  88.00   51
  7  ω    -75.00 -50.00   1.00    4.00    --  -17.59 133.00 -24.00   25
  8  ω    -77.00 -52.00   1.00    4.00    --  -17.59 136.00 153.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0133760000
_diffrn_orient_matrix_UB_12      0.0528692000
_diffrn_orient_matrix_UB_13      0.0375652000
_diffrn_orient_matrix_UB_21      -0.0225890000
_diffrn_orient_matrix_UB_22      0.0318289000
_diffrn_orient_matrix_UB_23      0.0090595000
_diffrn_orient_matrix_UB_31      -0.0002020000
_diffrn_orient_matrix_UB_32      -0.0535071000
_diffrn_orient_matrix_UB_33      0.0422748000
_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                3467
_reflns_number_total             6367
_reflns_odcompleteness_completeness 99.75
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     405
_refine_ls_number_reflns         6367
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.021
_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)+(0.0728P)²+0.1507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1865
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O003-H003
 0.85 with sigma of 0.02
 O001-H001
 0.85 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W),
 C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012),
 C013(H013), C014(H014), C015(H015), C016(H016), C017(H017), C018(H018)
;
_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 0.04049(7) 0.3907(2) 0.09373(17) 0.0650(6) Uani 1 1 d D . . . .
O002 O 0.00335(7) 0.6121(2) 0.11019(16) 0.0692(6) Uani 1 1 d . . . . .
O003 O 0.45080(7) 0.0244(2) 0.0755(2) 0.0751(6) Uani 1 1 d D . . . .
N004 N 0.37228(7) 0.1544(2) 0.14946(18) 0.0502(5) Uani 1 1 d . . . . .
N005 N 0.12319(7) 0.3395(2) 0.25087(18) 0.0512(5) Uani 1 1 d . . . . .
O006 O 0.49680(8) 0.1863(2) 0.0033(2) 0.0863(7) Uani 1 1 d . . . . .
C007 C 0.03134(8) 0.5045(3) 0.1493(2) 0.0456(6) Uani 1 1 d . . . . .
C008 C 0.05283(8) 0.5069(3) 0.2662(2) 0.0469(6) Uani 1 1 d . . . . .
C009 C 0.15278(8) 0.4036(3) 0.1858(2) 0.0493(6) Uani 1 1 d . . . . .
C00A C 0.44682(8) 0.2895(3) 0.1171(2) 0.0483(6) Uani 1 1 d . . . . .
C00B C 0.33691(8) 0.1229(3) 0.0576(2) 0.0502(6) Uani 1 1 d . . . . .
C00C C 0.09454(8) 0.4230(3) 0.3129(2) 0.0489(6) Uani 1 1 d . . . . .
C00D C 0.36905(8) 0.0438(3) 0.2262(2) 0.0493(6) Uani 1 1 d . . . . .
C00E C 0.40463(8) 0.2846(3) 0.1623(2) 0.0495(6) Uani 1 1 d . . . . .
C00F C 0.31124(8) -0.0103(3) 0.0759(2) 0.0521(7) Uani 1 1 d . . . . .
C00G C 0.33166(8) -0.0606(3) 0.1836(2) 0.0512(7) Uani 1 1 d . . . . .
C00H C 0.46603(9) 0.1611(3) 0.0598(2) 0.0515(7) Uani 1 1 d . . . . .
C00I C 0.17540(8) 0.1539(3) 0.2140(2) 0.0545(7) Uani 1 1 d . . . . .
C00J C 0.13674(9) 0.1855(3) 0.2685(2) 0.0521(7) Uani 1 1 d . . . . .
C00K C 0.18564(9) 0.2925(3) 0.1604(2) 0.0539(7) Uani 1 1 d . . . . .
C00L C 0.39654(9) 0.0309(3) 0.3304(2) 0.0567(7) Uani 1 1 d . . . . .
H00L H 0.4220 0.1022 0.3582 0.068 Uiso 1 1 calc R . . . .
C00M C 0.15372(10) 0.5530(3) 0.1487(2) 0.0607(7) Uani 1 1 d . . . . .
H00M H 0.1312 0.6284 0.1651 0.073 Uiso 1 1 calc R . . . .
C00N C 0.47483(9) 0.4231(3) 0.1288(2) 0.0590(7) Uani 1 1 d . . . . .
H00N H 0.5036 0.4281 0.0978 0.071 Uiso 1 1 calc R . . . .
C00O C 0.02904(10) 0.5940(3) 0.3325(2) 0.0631(8) Uani 1 1 d . . . . .
H00O H 0.0013 0.6550 0.3012 0.076 Uiso 1 1 calc R . . . .
C00P C 0.32525(9) 0.2060(3) -0.0373(2) 0.0622(7) Uani 1 1 d . . . . .
H00P H 0.3430 0.2966 -0.0481 0.075 Uiso 1 1 calc R . . . .
C00Q C 0.32101(10) -0.1805(3) 0.2483(3) 0.0651(8) Uani 1 1 d . . . . .
H00Q H 0.2956 -0.2525 0.2215 0.078 Uiso 1 1 calc R . . . .
C00R C 0.27325(9) -0.0604(3) -0.0059(3) 0.0654(8) Uani 1 1 d . . . . .
H00R H 0.2553 -0.1510 0.0039 0.078 Uiso 1 1 calc R . . . .
C00S C 0.21980(10) 0.3322(4) 0.0973(3) 0.0691(8) Uani 1 1 d . . . . .
H00S H 0.2421 0.2575 0.0793 0.083 Uiso 1 1 calc R . . . .
C00T C 0.11012(10) 0.4261(3) 0.4238(2) 0.0693(9) Uani 1 1 d . . . . .
H00T H 0.1386 0.3690 0.4557 0.083 Uiso 1 1 calc R . . . .
C00U C 0.34776(11) -0.1935(3) 0.3519(3) 0.0726(9) Uani 1 1 d . . . . .
H00U H 0.3404 -0.2746 0.3967 0.087 Uiso 1 1 calc R . . . .
C00V C 0.11648(10) 0.0751(3) 0.3248(3) 0.0692(8) Uani 1 1 d . . . . .
H00V H 0.0897 0.0982 0.3596 0.083 Uiso 1 1 calc R . . . .
C00W C 0.46221(10) 0.5476(3) 0.1836(3) 0.0681(8) Uani 1 1 d . . . . .
H00W H 0.4820 0.6380 0.1903 0.082 Uiso 1 1 calc R . . . .
C00X C 0.19563(11) 0.0062(3) 0.2219(3) 0.0733(9) Uani 1 1 d . . . . .
H00X H 0.2225 -0.0181 0.1874 0.088 Uiso 1 1 calc R . . . .
C00Y C 0.39216(10) 0.4101(3) 0.2173(3) 0.0721(9) Uani 1 1 d . . . . .
H00Y H 0.3633 0.4064 0.2480 0.087 Uiso 1 1 calc R . . . .
C00Z C 0.04452(11) 0.5945(4) 0.4424(3) 0.0758(9) Uani 1 1 d . . . . .
H00Z H 0.0271 0.6531 0.4866 0.091 Uiso 1 1 calc R . . . .
C010 C 0.28726(10) 0.1534(4) -0.1155(3) 0.0704(8) Uani 1 1 d . . . . .
H010 H 0.2783 0.2091 -0.1810 0.084 Uiso 1 1 calc R . . . .
C011 C 0.38491(11) -0.0911(4) 0.3914(3) 0.0706(8) Uani 1 1 d . . . . .
H011 H 0.4031 -0.1044 0.4627 0.085 Uiso 1 1 calc R . . . .
C012 C 0.26173(10) 0.0201(4) -0.1002(3) 0.0736(9) Uani 1 1 d . . . . .
H012 H 0.2360 -0.0156 -0.1560 0.088 Uiso 1 1 calc R . . . .
C013 C 0.18845(12) 0.5890(4) 0.0872(3) 0.0759(9) Uani 1 1 d . . . . .
H013 H 0.1901 0.6915 0.0617 0.091 Uiso 1 1 calc R . . . .
C014 C 0.08527(12) 0.5100(4) 0.4884(3) 0.0827(10) Uani 1 1 d . . . . .
H014 H 0.0962 0.5096 0.5644 0.099 Uiso 1 1 calc R . . . .
C015 C 0.17648(14) -0.1027(4) 0.2795(3) 0.0859(12) Uani 1 1 d . . . . .
H015 H 0.1907 -0.2027 0.2861 0.103 Uiso 1 1 calc R . . . .
C016 C 0.13687(13) -0.0718(3) 0.3288(3) 0.0808(10) Uani 1 1 d . . . . .
H016 H 0.1234 -0.1517 0.3657 0.097 Uiso 1 1 calc R . . . .
C017 C 0.42092(11) 0.5419(4) 0.2288(3) 0.0811(10) Uani 1 1 d . . . . .
H017 H 0.4121 0.6276 0.2678 0.097 Uiso 1 1 calc R . . . .
C018 C 0.22085(11) 0.4806(4) 0.0615(3) 0.0813(10) Uani 1 1 d . . . . .
H018 H 0.2442 0.5091 0.0184 0.098 Uiso 1 1 calc R . . . .
H001 H 0.0257(14) 0.391(5) 0.0233(18) 0.148(17) Uiso 1 1 d D . . . .
H003 H 0.4676(13) -0.046(4) 0.046(4) 0.17(2) Uiso 1 1 d 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
O001 C007 1.265(3) . ?
O001 H001 0.904(19) . ?
O002 C007 1.250(3) . ?
O003 C00H 1.286(3) . ?
O003 H003 0.886(19) . ?
N004 C00B 1.391(3) . ?
N004 C00D 1.379(3) . ?
N004 C00E 1.429(3) . ?
N005 C009 1.381(3) . ?
N005 C00C 1.414(3) . ?
N005 C00J 1.394(3) . ?
O006 C00H 1.228(3) . ?
C007 C008 1.483(3) . ?
C008 C00C 1.392(3) . ?
C008 C00O 1.383(4) . ?
C009 C00K 1.401(3) . ?
C009 C00M 1.381(4) . ?
C00A C00E 1.389(3) . ?
C00A C00H 1.481(4) . ?
C00A C00N 1.384(3) . ?
C00B C00F 1.397(3) . ?
C00B C00P 1.384(4) . ?
C00C C00T 1.385(4) . ?
C00D C00G 1.399(3) . ?
C00D C00L 1.392(4) . ?
C00E C00Y 1.371(4) . ?
C00F C00G 1.437(4) . ?
C00F C00R 1.391(4) . ?
C00G C00Q 1.389(4) . ?
C00I C00J 1.401(4) . ?
C00I C00K 1.435(4) . ?
C00I C00X 1.394(4) . ?
C00J C00V 1.374(4) . ?
C00K C00S 1.388(4) . ?
C00L H00L 0.9500 . ?
C00L C011 1.383(4) . ?
C00M H00M 0.9500 . ?
C00M C013 1.379(4) . ?
C00N H00N 0.9500 . ?
C00N C00W 1.365(4) . ?
C00O H00O 0.9500 . ?
C00O C00Z 1.372(4) . ?
C00P H00P 0.9500 . ?
C00P C010 1.371(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C00U 1.377(4) . ?
C00R H00R 0.9500 . ?
C00R C012 1.365(4) . ?
C00S H00S 0.9500 . ?
C00S C018 1.368(4) . ?
C00T H00T 0.9500 . ?
C00T C014 1.370(4) . ?
C00U H00U 0.9500 . ?
C00U C011 1.374(4) . ?
C00V H00V 0.9500 . ?
C00V C016 1.390(4) . ?
C00W H00W 0.9500 . ?
C00W C017 1.367(4) . ?
C00X H00X 0.9500 . ?
C00X C015 1.360(5) . ?
C00Y H00Y 0.9500 . ?
C00Y C017 1.383(4) . ?
C00Z H00Z 0.9500 . ?
C00Z C014 1.372(4) . ?
C010 H010 0.9500 . ?
C010 C012 1.386(4) . ?
C011 H011 0.9500 . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C013 C018 1.377(4) . ?
C014 H014 0.9500 . ?
C015 H015 0.9500 . ?
C015 C016 1.381(5) . ?
C016 H016 0.9500 . ?
C017 H017 0.9500 . ?
C018 H018 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 O001 H001 116(3) . . ?
C00H O003 H003 111(3) . . ?
C00B N004 C00E 124.8(2) . . ?
C00D N004 C00B 108.69(19) . . ?
C00D N004 C00E 126.4(2) . . ?
C009 N005 C00C 125.3(2) . . ?
C009 N005 C00J 108.2(2) . . ?
C00J N005 C00C 124.3(2) . . ?
O001 C007 C008 118.7(2) . . ?
O002 C007 O001 122.5(2) . . ?
O002 C007 C008 118.7(2) . . ?
C00C C008 C007 123.6(2) . . ?
C00O C008 C007 117.9(2) . . ?
C00O C008 C00C 118.5(2) . . ?
N005 C009 C00K 109.8(2) . . ?
N005 C009 C00M 129.2(2) . . ?
C00M C009 C00K 121.0(3) . . ?
C00E C00A C00H 125.6(2) . . ?
C00N C00A C00E 118.3(2) . . ?
C00N C00A C00H 116.1(2) . . ?
N004 C00B C00F 108.6(2) . . ?
C00P C00B N004 129.0(2) . . ?
C00P C00B C00F 122.3(2) . . ?
C008 C00C N005 122.4(2) . . ?
C00T C00C N005 118.3(2) . . ?
C00T C00C C008 119.2(2) . . ?
N004 C00D C00G 108.8(2) . . ?
N004 C00D C00L 128.7(2) . . ?
C00L C00D C00G 122.5(3) . . ?
C00A C00E N004 122.0(2) . . ?
C00Y C00E N004 118.4(2) . . ?
C00Y C00E C00A 119.6(2) . . ?
C00B C00F C00G 106.8(2) . . ?
C00R C00F C00B 117.9(3) . . ?
C00R C00F C00G 135.3(3) . . ?
C00D C00G C00F 107.0(2) . . ?
C00Q C00G C00D 118.8(3) . . ?
C00Q C00G C00F 134.2(2) . . ?
O003 C00H C00A 117.5(2) . . ?
O006 C00H O003 122.4(2) . . ?
O006 C00H C00A 120.1(2) . . ?
C00J C00I C00K 107.7(2) . . ?
C00X C00I C00J 118.4(3) . . ?
C00X C00I C00K 133.9(3) . . ?
N005 C00J C00I 108.3(2) . . ?
C00V C00J N005 129.0(3) . . ?
C00V C00J C00I 122.7(2) . . ?
C009 C00K C00I 106.0(2) . . ?
C00S C00K C009 119.9(3) . . ?
C00S C00K C00I 134.0(3) . . ?
C00D C00L H00L 121.7 . . ?
C011 C00L C00D 116.6(3) . . ?
C011 C00L H00L 121.7 . . ?
C009 C00M H00M 121.2 . . ?
C013 C00M C009 117.7(3) . . ?
C013 C00M H00M 121.2 . . ?
C00A C00N H00N 119.1 . . ?
C00W C00N C00A 121.8(3) . . ?
C00W C00N H00N 119.1 . . ?
C008 C00O H00O 119.2 . . ?
C00Z C00O C008 121.6(2) . . ?
C00Z C00O H00O 119.2 . . ?
C00B C00P H00P 121.0 . . ?
C010 C00P C00B 118.0(3) . . ?
C010 C00P H00P 121.0 . . ?
C00G C00Q H00Q 120.5 . . ?
C00U C00Q C00G 119.1(3) . . ?
C00U C00Q H00Q 120.5 . . ?
C00F C00R H00R 119.9 . . ?
C012 C00R C00F 120.3(3) . . ?
C012 C00R H00R 119.9 . . ?
C00K C00S H00S 120.5 . . ?
C018 C00S C00K 118.9(3) . . ?
C018 C00S H00S 120.5 . . ?
C00C C00T H00T 119.3 . . ?
C014 C00T C00C 121.4(2) . . ?
C014 C00T H00T 119.3 . . ?
C00Q C00U H00U 119.4 . . ?
C011 C00U C00Q 121.1(3) . . ?
C011 C00U H00U 119.4 . . ?
C00J C00V H00V 121.4 . . ?
C00J C00V C016 117.2(3) . . ?
C016 C00V H00V 121.4 . . ?
C00N C00W H00W 120.1 . . ?
C00N C00W C017 119.7(3) . . ?
C017 C00W H00W 120.1 . . ?
C00I C00X H00X 120.4 . . ?
C015 C00X C00I 119.2(3) . . ?
C015 C00X H00X 120.4 . . ?
C00E C00Y H00Y 119.4 . . ?
C00E C00Y C017 121.2(3) . . ?
C017 C00Y H00Y 119.4 . . ?
C00O C00Z H00Z 120.1 . . ?
C014 C00Z C00O 119.7(3) . . ?
C014 C00Z H00Z 120.1 . . ?
C00P C010 H010 119.5 . . ?
C00P C010 C012 121.0(3) . . ?
C012 C010 H010 119.5 . . ?
C00L C011 H011 119.1 . . ?
C00U C011 C00L 121.9(3) . . ?
C00U C011 H011 119.1 . . ?
C00R C012 C010 120.6(3) . . ?
C00R C012 H012 119.7 . . ?
C010 C012 H012 119.7 . . ?
C00M C013 H013 119.1 . . ?
C018 C013 C00M 121.9(3) . . ?
C018 C013 H013 119.1 . . ?
C00T C014 C00Z 119.5(3) . . ?
C00T C014 H014 120.2 . . ?
C00Z C014 H014 120.2 . . ?
C00X C015 H015 119.1 . . ?
C00X C015 C016 121.8(3) . . ?
C016 C015 H015 119.1 . . ?
C00V C016 H016 119.7 . . ?
C015 C016 C00V 120.6(3) . . ?
C015 C016 H016 119.7 . . ?
C00W C017 C00Y 119.4(3) . . ?
C00W C017 H017 120.3 . . ?
C00Y C017 H017 120.3 . . ?
C00S C018 C013 120.7(3) . . ?
C00S C018 H018 119.7 . . ?
C013 C018 H018 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.784
_oxdiff_exptl_absorpt_empirical_full_min 0.294
####################################################################### 
# 
# 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_zz26cult
_audit_block_doi                 10.5517/ccdc.csd.cc2pmfc4
_database_code_depnum_ccdc_archive 'CCDC 2491326'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2017-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H13 N O2, C2 H6 O'
_chemical_formula_sum            'C21 H19 N O3'
_chemical_formula_weight         333.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.52527(11)
_cell_length_b                   26.3892(3)
_cell_length_c                   15.8287(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.7347(13)
_cell_angle_gamma                90
_cell_volume                     3498.73(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      75.5100
_cell_measurement_theta_min      4.3750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.683
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89795
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10672
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_min         4.394
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     38.00 117.00   1.00    3.00    --  110.57 -61.00-150.00   79
  2  ω     20.00 110.00   1.00    1.50    --   40.57  37.00 -60.00   90
  3  ω     56.00 115.00   1.00    3.00    --  110.57-111.00-120.00   59
  4  ω     48.00 107.00   1.00    3.00    --  110.57 -94.00   0.00   59
  5  ω     46.00 134.00   1.00    3.00    --  110.57 -45.00 -30.00   88
  6  ω     86.00 176.00   1.00    3.00    --  110.57  30.00 150.00   90
  7  ω    -95.00  -3.00   1.00    1.50    --  -40.57 125.00 -60.00   92
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1666856000
_diffrn_orient_matrix_UB_12      -0.0183219000
_diffrn_orient_matrix_UB_13      -0.0107632000
_diffrn_orient_matrix_UB_21      -0.0635361000
_diffrn_orient_matrix_UB_22      -0.0095410000
_diffrn_orient_matrix_UB_23      -0.0962820000
_diffrn_orient_matrix_UB_31      0.0448127000
_diffrn_orient_matrix_UB_32      0.0546289000
_diffrn_orient_matrix_UB_33      -0.0205077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5328
_reflns_number_total             6229
_reflns_odcompleteness_completeness 98.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0033(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         6229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.001
_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)+(0.0890P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1328
_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, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: C31A(0.8) H31A(0.8) H31B(0.8) C31B(0.2) H31C(0.2) H31D(0.2)
 H32A(0.8) H32B(0.8) H32C(0.8) H32D(0.2) H32E(0.2) H32F(0.2)
3.a Secondary CH2 refined with riding coordinates:
 C31(H31E,H31F), C31A(H31A,H31B), C31B(H31C,H31D)
3.b Me refined with riding coordinates:
 C32A(H32A,H32B,H32C), C32A(H32D,H32E,H32F)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C18(H18), C19(H19), C20(H20), C21(H21), C3A(H3A), C4A(H4A), C5A(H5A), C6A(H6A),
  C12A(H12A), C13A(H13A), C14A(H14A), C15A(H15A), C18A(H18A), C19A(H19A),
 C20A(H20A), C21A(H21A)
3.d Tetrahedral OH refined with riding coordinates:
 O3A(H3AA)
3.e Idealised Me refined as rotating group:
 C32(H32G,H32H,H32I)
3.f Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3B), O2A(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.44627(15) 0.61996(4) 0.25638(9) 0.0582(3) Uani 1 1 d . . . . .
O2 O 0.49574(13) 0.55791(4) 0.17100(7) 0.0507(3) Uani 1 1 d . . . . .
H2 H 0.4130 0.5459 0.1835 0.076 Uiso 1 1 calc GR . . . .
N1 N 0.62653(13) 0.70854(4) 0.24931(7) 0.0357(3) Uani 1 1 d . . . . .
C1 C 0.68371(16) 0.62337(5) 0.19647(9) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.72973(16) 0.67335(5) 0.21887(9) 0.0357(3) Uani 1 1 d . . . . .
C3 C 0.87991(17) 0.69059(6) 0.20966(10) 0.0442(3) Uani 1 1 d . . . . .
H3 H 0.9100 0.7242 0.2245 0.053 Uiso 1 1 calc R . . . .
C4 C 0.98492(18) 0.65888(6) 0.17895(11) 0.0504(4) Uani 1 1 d . . . . .
H4 H 1.0872 0.6705 0.1744 0.061 Uiso 1 1 calc R . . . .
C5 C 0.9394(2) 0.60989(6) 0.15479(11) 0.0515(4) Uani 1 1 d . . . . .
H5 H 1.0099 0.5884 0.1326 0.062 Uiso 1 1 calc R . . . .
C6 C 0.79071(19) 0.59249(5) 0.16320(10) 0.0445(3) Uani 1 1 d . . . . .
H6 H 0.7607 0.5592 0.1462 0.053 Uiso 1 1 calc R . . . .
C7 C 0.52939(17) 0.60101(5) 0.21126(9) 0.0369(3) Uani 1 1 d . . . . .
C11 C 0.48431(15) 0.72735(5) 0.20241(9) 0.0338(3) Uani 1 1 d . . . . .
C12 C 0.40469(17) 0.71416(5) 0.12077(9) 0.0397(3) Uani 1 1 d . . . . .
H12 H 0.4443 0.6888 0.0887 0.048 Uiso 1 1 calc R . . . .
C13 C 0.26445(18) 0.73985(6) 0.08823(10) 0.0466(4) Uani 1 1 d . . . . .
H13 H 0.2085 0.7318 0.0329 0.056 Uiso 1 1 calc R . . . .
C14 C 0.20468(18) 0.77724(6) 0.13567(12) 0.0511(4) Uani 1 1 d . . . . .
H14 H 0.1086 0.7937 0.1124 0.061 Uiso 1 1 calc R . . . .
C15 C 0.28538(18) 0.79036(6) 0.21663(11) 0.0466(4) Uani 1 1 d . . . . .
H15 H 0.2451 0.8157 0.2484 0.056 Uiso 1 1 calc R . . . .
C16 C 0.42735(16) 0.76550(5) 0.25076(9) 0.0363(3) Uani 1 1 d . . . . .
C17 C 0.54106(16) 0.77033(5) 0.32998(9) 0.0376(3) Uani 1 1 d . . . . .
C18 C 0.55263(19) 0.80216(6) 0.40160(11) 0.0490(4) Uani 1 1 d . . . . .
H18 H 0.4732 0.8264 0.4047 0.059 Uiso 1 1 calc R . . . .
C19 C 0.6824(2) 0.79737(7) 0.46759(11) 0.0550(4) Uani 1 1 d . . . . .
H19 H 0.6923 0.8190 0.5155 0.066 Uiso 1 1 calc R . . . .
C20 C 0.7990(2) 0.76084(7) 0.46413(10) 0.0526(4) Uani 1 1 d . . . . .
H20 H 0.8849 0.7578 0.5106 0.063 Uiso 1 1 calc R . . . .
C21 C 0.79172(18) 0.72898(6) 0.39411(10) 0.0441(3) Uani 1 1 d . . . . .
H21 H 0.8710 0.7045 0.3921 0.053 Uiso 1 1 calc R . . . .
C22 C 0.66253(16) 0.73460(5) 0.32683(9) 0.0354(3) Uani 1 1 d . . . . .
O3 O 0.22962(17) 0.61361(6) 0.36535(10) 0.0741(4) Uani 1 1 d . . . . .
H3B H 0.2897 0.6093 0.3303 0.111 Uiso 1 1 calc GR . . . .
C31 C 0.2642(2) 0.66195(8) 0.40779(15) 0.0711(5) Uani 1 1 d . . . . .
H31E H 0.1842 0.6691 0.4433 0.085 Uiso 1 1 calc R . . . .
H31F H 0.2581 0.6888 0.3645 0.085 Uiso 1 1 calc R . . . .
C32 C 0.4228(3) 0.66187(9) 0.46172(15) 0.0784(6) Uani 1 1 d . . . . .
H32G H 0.4296 0.6349 0.5038 0.118 Uiso 1 1 calc GR . . . .
H32H H 0.4419 0.6942 0.4911 0.118 Uiso 1 1 calc GR . . . .
H32I H 0.5025 0.6565 0.4261 0.118 Uiso 1 1 calc GR . . . .
O1A O 0.03157(15) 0.50803(4) 0.30002(8) 0.0578(3) Uani 1 1 d . . . . .
O2A O -0.02430(18) 0.56779(6) 0.38737(10) 0.0789(5) Uani 1 1 d . . . . .
H2A H 0.0632 0.5790 0.3802 0.118 Uiso 1 1 calc GR . . . .
N1A N -0.16503(14) 0.42418(4) 0.27669(7) 0.0380(3) Uani 1 1 d . . . . .
C1A C -0.21116(17) 0.50250(5) 0.35428(8) 0.0381(3) Uani 1 1 d . . . . .
C2A C -0.26121(17) 0.45509(5) 0.32034(8) 0.0371(3) Uani 1 1 d . . . . .
C3A C -0.41191(19) 0.43694(6) 0.32597(10) 0.0467(4) Uani 1 1 d . . . . .
H3A H -0.4442 0.4048 0.3036 0.056 Uiso 1 1 calc R . . . .
C4A C -0.5147(2) 0.46580(7) 0.36426(11) 0.0537(4) Uani 1 1 d . . . . .
H4A H -0.6171 0.4535 0.3672 0.064 Uiso 1 1 calc R . . . .
C5A C -0.4668(2) 0.51265(7) 0.39817(10) 0.0516(4) Uani 1 1 d . . . . .
H5A H -0.5365 0.5323 0.4242 0.062 Uiso 1 1 calc R . . . .
C6A C -0.3163(2) 0.53062(6) 0.39393(10) 0.0466(4) Uani 1 1 d . . . . .
H6A H -0.2839 0.5623 0.4181 0.056 Uiso 1 1 calc R . . . .
C7A C -0.05516(19) 0.52529(6) 0.34465(9) 0.0430(3) Uani 1 1 d . . . . .
C11A C -0.02797(16) 0.39774(5) 0.31262(10) 0.0385(3) Uani 1 1 d . . . . .
C12A C 0.04700(18) 0.39449(6) 0.39812(10) 0.0455(3) Uani 1 1 d . . . . .
H12A H 0.0086 0.4122 0.4416 0.055 Uiso 1 1 calc R . . . .
C13A C 0.1808(2) 0.36392(6) 0.41647(12) 0.0548(4) Uani 1 1 d . . . . .
H13A H 0.2340 0.3606 0.4738 0.066 Uiso 1 1 calc R . . . .
C14A C 0.2389(2) 0.33777(6) 0.35153(14) 0.0617(5) Uani 1 1 d . . . . .
H14A H 0.3308 0.3175 0.3659 0.074 Uiso 1 1 calc R . . . .
C15A C 0.1635(2) 0.34134(6) 0.26749(13) 0.0540(4) Uani 1 1 d . . . . .
H15A H 0.2031 0.3236 0.2244 0.065 Uiso 1 1 calc R . . . .
C16A C 0.02780(17) 0.37141(5) 0.24640(10) 0.0421(3) Uani 1 1 d . . . . .
C17A C -0.08075(18) 0.38289(5) 0.16725(10) 0.0409(3) Uani 1 1 d . . . . .
C18A C -0.0903(2) 0.36898(6) 0.08095(11) 0.0519(4) Uani 1 1 d . . . . .
H18A H -0.0148 0.3467 0.0650 0.062 Uiso 1 1 calc R . . . .
C19A C -0.2114(2) 0.38833(7) 0.01992(11) 0.0549(4) Uani 1 1 d . . . . .
H19A H -0.2183 0.3790 -0.0380 0.066 Uiso 1 1 calc R . . . .
C20A C -0.3243(2) 0.42150(7) 0.04221(10) 0.0529(4) Uani 1 1 d . . . . .
H20A H -0.4057 0.4342 -0.0009 0.063 Uiso 1 1 calc R . . . .
C21A C -0.31822(19) 0.43602(6) 0.12704(10) 0.0458(4) Uani 1 1 d . . . . .
H21A H -0.3935 0.4586 0.1423 0.055 Uiso 1 1 calc R . . . .
C22A C -0.19687(17) 0.41588(5) 0.18841(9) 0.0381(3) Uani 1 1 d . . . . .
O3A O 0.23050(14) 0.51553(5) 0.18397(8) 0.0607(3) Uani 1 1 d . . . . .
H3AA H 0.1785 0.5152 0.2234 0.091 Uiso 1 1 calc R . . A 1
C31A C 0.1439(3) 0.48864(9) 0.11104(17) 0.0554(5) Uani 0.8 1 d . . P B 1
H31A H 0.0551 0.4704 0.1287 0.066 Uiso 0.8 1 calc R . P B 1
H31B H 0.0982 0.5133 0.0670 0.066 Uiso 0.8 1 calc R . P B 1
C31B C 0.2103(15) 0.4685(3) 0.1527(6) 0.061(2) Uani 0.2 1 d . . P B 2
H31C H 0.0991 0.4595 0.1537 0.073 Uiso 0.2 1 calc R . P B 2
H31D H 0.2762 0.4466 0.1951 0.073 Uiso 0.2 1 calc R . P B 2
C32A C 0.2381(3) 0.45327(11) 0.07397(18) 0.0933(8) Uani 1 1 d . . . . .
H32A H 0.1720 0.4367 0.0253 0.140 Uiso 0.8 1 calc R . P B 1
H32B H 0.3248 0.4710 0.0548 0.140 Uiso 0.8 1 calc R . P B 1
H32C H 0.2816 0.4281 0.1166 0.140 Uiso 0.8 1 calc R . P B 1
H32D H 0.2146 0.4174 0.0663 0.140 Uiso 0.2 1 calc R . P B 2
H32E H 0.1702 0.4724 0.0291 0.140 Uiso 0.2 1 calc R . P B 2
H32F H 0.3492 0.4593 0.0709 0.140 Uiso 0.2 1 calc R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.2044(18) . ?
O2 C7 1.3093(17) . ?
N1 C2 1.4236(17) . ?
N1 C11 1.3901(17) . ?
N1 C22 1.3901(17) . ?
C1 C2 1.4026(19) . ?
C1 C6 1.3974(19) . ?
C1 C7 1.4996(19) . ?
C2 C3 1.392(2) . ?
C3 C4 1.379(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.377(2) . ?
C11 C12 1.3875(19) . ?
C11 C16 1.4046(19) . ?
C12 C13 1.387(2) . ?
C13 C14 1.393(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.394(2) . ?
C16 C17 1.441(2) . ?
C17 C18 1.400(2) . ?
C17 C22 1.4082(19) . ?
C18 C19 1.378(2) . ?
C19 C20 1.393(3) . ?
C20 C21 1.383(2) . ?
C21 C22 1.390(2) . ?
O3 C31 1.446(2) . ?
C31 C32 1.459(3) . ?
O1A C7A 1.2032(18) . ?
O2A C7A 1.3109(19) . ?
N1A C2A 1.4234(17) . ?
N1A C11A 1.3886(18) . ?
N1A C22A 1.3903(18) . ?
C1A C2A 1.397(2) . ?
C1A C6A 1.399(2) . ?
C1A C7A 1.493(2) . ?
C2A C3A 1.389(2) . ?
C3A C4A 1.383(2) . ?
C4A C5A 1.379(3) . ?
C5A C6A 1.382(2) . ?
C11A C12A 1.387(2) . ?
C11A C16A 1.412(2) . ?
C12A C13A 1.383(2) . ?
C13A C14A 1.403(3) . ?
C14A C15A 1.369(3) . ?
C15A C16A 1.391(2) . ?
C16A C17A 1.444(2) . ?
C17A C18A 1.402(2) . ?
C17A C22A 1.405(2) . ?
C18A C19A 1.374(3) . ?
C19A C20A 1.394(3) . ?
C20A C21A 1.388(2) . ?
C21A C22A 1.386(2) . ?
O3A C31A 1.437(3) . ?
O3A C31B 1.336(9) . ?
C31A C32A 1.427(3) . ?
C31B C32A 1.371(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C2 125.79(11) . . ?
C11 N1 C22 108.78(11) . . ?
C22 N1 C2 124.94(11) . . ?
C2 C1 C7 122.87(12) . . ?
C6 C1 C2 118.18(13) . . ?
C6 C1 C7 118.86(12) . . ?
C1 C2 N1 122.52(12) . . ?
C3 C2 N1 117.44(12) . . ?
C3 C2 C1 120.02(13) . . ?
C4 C3 C2 120.59(14) . . ?
C3 C4 C5 119.84(14) . . ?
C6 C5 C4 120.07(14) . . ?
C5 C6 C1 121.25(14) . . ?
O1 C7 O2 123.33(13) . . ?
O1 C7 C1 124.02(13) . . ?
O2 C7 C1 112.64(12) . . ?
N1 C11 C16 108.69(12) . . ?
C12 C11 N1 129.39(12) . . ?
C12 C11 C16 121.90(12) . . ?
C13 C12 C11 117.48(13) . . ?
C12 C13 C14 121.50(14) . . ?
C15 C14 C13 120.59(14) . . ?
C14 C15 C16 119.21(14) . . ?
C11 C16 C17 107.03(12) . . ?
C15 C16 C11 119.30(13) . . ?
C15 C16 C17 133.66(13) . . ?
C18 C17 C16 133.84(13) . . ?
C18 C17 C22 119.29(14) . . ?
C22 C17 C16 106.85(12) . . ?
C19 C18 C17 118.96(15) . . ?
C18 C19 C20 120.76(15) . . ?
C21 C20 C19 121.75(15) . . ?
C20 C21 C22 117.37(14) . . ?
N1 C22 C17 108.64(12) . . ?
C21 C22 N1 129.54(13) . . ?
C21 C22 C17 121.82(13) . . ?
O3 C31 C32 110.93(18) . . ?
C11A N1A C2A 127.30(11) . . ?
C11A N1A C22A 108.93(11) . . ?
C22A N1A C2A 123.77(12) . . ?
C2A C1A C6A 118.19(13) . . ?
C2A C1A C7A 122.39(13) . . ?
C6A C1A C7A 119.29(13) . . ?
C1A C2A N1A 122.53(13) . . ?
C3A C2A N1A 117.17(13) . . ?
C3A C2A C1A 120.27(13) . . ?
C4A C3A C2A 120.48(15) . . ?
C5A C4A C3A 119.87(15) . . ?
C4A C5A C6A 119.96(14) . . ?
C5A C6A C1A 121.20(15) . . ?
O1A C7A O2A 122.71(15) . . ?
O1A C7A C1A 124.33(14) . . ?
O2A C7A C1A 112.90(13) . . ?
N1A C11A C16A 108.50(13) . . ?
C12A C11A N1A 129.06(13) . . ?
C12A C11A C16A 122.42(14) . . ?
C13A C12A C11A 116.94(15) . . ?
C12A C13A C14A 121.54(17) . . ?
C15A C14A C13A 120.82(15) . . ?
C14A C15A C16A 119.42(16) . . ?
C11A C16A C17A 106.90(13) . . ?
C15A C16A C11A 118.86(15) . . ?
C15A C16A C17A 134.23(15) . . ?
C18A C17A C16A 134.56(15) . . ?
C18A C17A C22A 118.62(15) . . ?
C22A C17A C16A 106.82(12) . . ?
C19A C18A C17A 119.15(16) . . ?
C18A C19A C20A 121.28(15) . . ?
C21A C20A C19A 121.00(16) . . ?
C22A C21A C20A 117.42(15) . . ?
N1A C22A C17A 108.84(13) . . ?
C21A C22A N1A 128.63(13) . . ?
C21A C22A C17A 122.52(14) . . ?
C32A C31A O3A 114.1(2) . . ?
O3A C31B C32A 125.2(7) . . ?

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
O2 H2 O3A 0.83 1.75 2.5649(15) 166.0 .
O3 H3B O1 0.83 1.95 2.7570(17) 163.1 .
O2A H2A O3 0.83 1.74 2.5593(18) 169.2 .
O3A H3AA O1A 0.83 1.91 2.7295(16) 169.8 .

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
N1 C2 C3 C4 -178.75(14) . . . . ?
N1 C11 C12 C13 -178.91(13) . . . . ?
N1 C11 C16 C15 179.75(13) . . . . ?
N1 C11 C16 C17 0.64(15) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 N1 C11 C12 5.6(2) . . . . ?
C2 N1 C11 C16 -172.94(12) . . . . ?
C2 N1 C22 C17 172.80(12) . . . . ?
C2 N1 C22 C21 -7.8(2) . . . . ?
C2 C1 C6 C5 1.9(2) . . . . ?
C2 C1 C7 O1 -13.8(2) . . . . ?
C2 C1 C7 O2 167.47(13) . . . . ?
C2 C3 C4 C5 1.8(2) . . . . ?
C3 C4 C5 C6 -1.4(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 N1 176.87(13) . . . . ?
C6 C1 C2 C3 -1.5(2) . . . . ?
C6 C1 C7 O1 162.68(15) . . . . ?
C6 C1 C7 O2 -16.07(19) . . . . ?
C7 C1 C2 N1 -6.7(2) . . . . ?
C7 C1 C2 C3 174.97(13) . . . . ?
C7 C1 C6 C5 -174.75(14) . . . . ?
C11 N1 C2 C1 -65.04(18) . . . . ?
C11 N1 C2 C3 113.38(15) . . . . ?
C11 N1 C22 C17 0.48(15) . . . . ?
C11 N1 C22 C21 179.89(14) . . . . ?
C11 C12 C13 C14 -0.5(2) . . . . ?
C11 C16 C17 C18 177.89(16) . . . . ?
C11 C16 C17 C22 -0.34(15) . . . . ?
C12 C11 C16 C15 1.1(2) . . . . ?
C12 C11 C16 C17 -178.02(12) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C13 C14 C15 C16 -0.4(2) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C14 C15 C16 C17 178.22(15) . . . . ?
C15 C16 C17 C18 -1.0(3) . . . . ?
C15 C16 C17 C22 -179.27(15) . . . . ?
C16 C11 C12 C13 -0.5(2) . . . . ?
C16 C17 C18 C19 -178.58(16) . . . . ?
C16 C17 C22 N1 -0.08(15) . . . . ?
C16 C17 C22 C21 -179.55(13) . . . . ?
C17 C18 C19 C20 -1.2(3) . . . . ?
C18 C17 C22 N1 -178.62(13) . . . . ?
C18 C17 C22 C21 1.9(2) . . . . ?
C18 C19 C20 C21 1.6(3) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C20 C21 C22 N1 179.14(14) . . . . ?
C20 C21 C22 C17 -1.5(2) . . . . ?
C22 N1 C2 C1 123.94(15) . . . . ?
C22 N1 C2 C3 -57.64(18) . . . . ?
C22 N1 C11 C12 177.83(13) . . . . ?
C22 N1 C11 C16 -0.70(14) . . . . ?
C22 C17 C18 C19 -0.5(2) . . . . ?
N1A C2A C3A C4A -177.29(14) . . . . ?
N1A C11A C12A C13A 178.12(14) . . . . ?
N1A C11A C16A C15A -178.93(13) . . . . ?
N1A C11A C16A C17A 0.27(15) . . . . ?
C1A C2A C3A C4A 0.8(2) . . . . ?
C2A N1A C11A C12A 0.7(2) . . . . ?
C2A N1A C11A C16A 179.04(13) . . . . ?
C2A N1A C22A C17A -178.77(12) . . . . ?
C2A N1A C22A C21A 2.4(2) . . . . ?
C2A C1A C6A C5A -1.2(2) . . . . ?
C2A C1A C7A O1A 8.4(2) . . . . ?
C2A C1A C7A O2A -174.36(15) . . . . ?
C2A C3A C4A C5A -0.9(2) . . . . ?
C3A C4A C5A C6A -0.1(3) . . . . ?
C4A C5A C6A C1A 1.2(2) . . . . ?
C6A C1A C2A N1A 178.22(13) . . . . ?
C6A C1A C2A C3A 0.3(2) . . . . ?
C6A C1A C7A O1A -167.55(15) . . . . ?
C6A C1A C7A O2A 9.7(2) . . . . ?
C7A C1A C2A N1A 2.3(2) . . . . ?
C7A C1A C2A C3A -175.70(14) . . . . ?
C7A C1A C6A C5A 174.87(14) . . . . ?
C11A N1A C2A C1A 72.05(19) . . . . ?
C11A N1A C2A C3A -109.94(16) . . . . ?
C11A N1A C22A C17A 1.15(15) . . . . ?
C11A N1A C22A C21A -177.70(14) . . . . ?
C11A C12A C13A C14A 0.6(2) . . . . ?
C11A C16A C17A C18A 179.70(15) . . . . ?
C11A C16A C17A C22A 0.42(15) . . . . ?
C12A C11A C16A C15A -0.4(2) . . . . ?
C12A C11A C16A C17A 178.77(13) . . . . ?
C12A C13A C14A C15A -0.7(3) . . . . ?
C13A C14A C15A C16A 0.2(3) . . . . ?
C14A C15A C16A C11A 0.4(2) . . . . ?
C14A C15A C16A C17A -178.56(15) . . . . ?
C15A C16A C17A C18A -1.3(3) . . . . ?
C15A C16A C17A C22A 179.44(16) . . . . ?
C16A C11A C12A C13A 0.0(2) . . . . ?
C16A C17A C18A C19A -178.61(15) . . . . ?
C16A C17A C22A N1A -0.96(15) . . . . ?
C16A C17A C22A C21A 177.98(13) . . . . ?
C17A C18A C19A C20A 0.2(2) . . . . ?
C18A C17A C22A N1A 179.63(12) . . . . ?
C18A C17A C22A C21A -1.4(2) . . . . ?
C18A C19A C20A C21A -0.2(2) . . . . ?
C19A C20A C21A C22A -0.6(2) . . . . ?
C20A C21A C22A N1A -179.87(14) . . . . ?
C20A C21A C22A C17A 1.4(2) . . . . ?
C22A N1A C2A C1A -108.05(16) . . . . ?
C22A N1A C2A C3A 69.96(18) . . . . ?
C22A N1A C11A C12A -179.24(14) . . . . ?
C22A N1A C11A C16A -0.87(15) . . . . ?
C22A C17A C18A C19A 0.6(2) . . . . ?

_olex2_date_sample_data_collection 2017-04-19
_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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.834
####################################################################### 
# 
# 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_zz27cult
_audit_block_doi                 10.5517/ccdc.csd.cc2pmfd5
_database_code_depnum_ccdc_archive 'CCDC 2491327'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2017-06-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H13 N O2, C3 H8 O'
_chemical_formula_sum            'C22 H21 N O3'
_chemical_formula_weight         347.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 CO2H N H15'
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                   8.50169(19)
_cell_length_b                   27.8458(5)
_cell_length_c                   8.11780(18)
_cell_angle_alpha                90
_cell_angle_beta                 103.313(2)
_cell_angle_gamma                90
_cell_volume                     1870.13(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3083
_cell_measurement_temperature    220.01(10)
_cell_measurement_theta_max      75.0020
_cell_measurement_theta_min      5.3470
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79299
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5491
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         67.500
_diffrn_reflns_theta_min         5.347
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    116.00 177.00   1.00    3.00    --  110.57 111.00  30.00   61
  2  ω    -70.00 -11.00   1.00    1.00    --  -40.57 125.00-180.00   59
  3  ω    -83.00  -7.00   1.00    1.00    --  -40.57 -77.00 120.00   76
  4  ω   -115.00 -14.00   1.00    1.00    --  -40.57 -57.00   0.00  101
  5  ω     84.00 178.00   1.00    3.00    --  110.57  30.00  90.00   94
  6  ω     83.00 175.00   1.00    3.00    --  110.57  45.00-180.00   92
  7  ω     31.00 108.00   1.00    3.00    --  110.57 -94.00 -30.00   77
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1819742000
_diffrn_orient_matrix_UB_12      0.0096831000
_diffrn_orient_matrix_UB_13      0.0212753000
_diffrn_orient_matrix_UB_21      0.0041126000
_diffrn_orient_matrix_UB_22      0.0263477000
_diffrn_orient_matrix_UB_23      0.1678764000
_diffrn_orient_matrix_UB_31      0.0394343000
_diffrn_orient_matrix_UB_32      -0.0476202000
_diffrn_orient_matrix_UB_33      0.0972733000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3311
_reflns_odcompleteness_completeness 98.44
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.0122(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.005
_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)+(0.0770P)²+0.3380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1323
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C12(H12),
 C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.51935(16) 0.43762(4) 0.30076(15) 0.0544(3) Uani 1 1 d . . . . .
O2 O 0.69684(15) 0.48888(5) 0.23972(16) 0.0601(4) Uani 1 1 d . . . . .
H2 H 0.6871 0.5015 0.3294 0.090 Uiso 1 1 calc GR . . . .
N1 N 0.47527(15) 0.35286(4) 0.10688(15) 0.0410(3) Uani 1 1 d . . . . .
C1 C 0.60386(17) 0.45093(5) 0.20867(18) 0.0386(3) Uani 1 1 d . . . . .
C2 C 0.61000(17) 0.42728(5) 0.04486(17) 0.0371(3) Uani 1 1 d . . . . .
C3 C 0.54309(17) 0.38204(5) -0.00252(17) 0.0382(3) Uani 1 1 d . . . . .
C4 C 0.5408(2) 0.36397(6) -0.16263(19) 0.0481(4) Uani 1 1 d . . . . .
H4 H 0.4967 0.3334 -0.1933 0.058 Uiso 1 1 calc R . . . .
C5 C 0.6025(2) 0.39048(7) -0.2772(2) 0.0537(4) Uani 1 1 d . . . . .
H5 H 0.5970 0.3785 -0.3866 0.064 Uiso 1 1 calc R . . . .
C6 C 0.6720(2) 0.43446(6) -0.2304(2) 0.0528(4) Uani 1 1 d . . . . .
H6 H 0.7162 0.4522 -0.3072 0.063 Uiso 1 1 calc R . . . .
C7 C 0.6771(2) 0.45261(6) -0.0709(2) 0.0462(4) Uani 1 1 d . . . . .
H7 H 0.7265 0.4825 -0.0398 0.055 Uiso 1 1 calc R . . . .
C8 C 0.55741(19) 0.33118(5) 0.25520(18) 0.0400(3) Uani 1 1 d . . . . .
C9 C 0.7204(2) 0.33249(5) 0.33094(19) 0.0445(4) Uani 1 1 d . . . . .
H9 H 0.7930 0.3508 0.2852 0.053 Uiso 1 1 calc R . . . .
C10 C 0.7726(3) 0.30562(6) 0.4774(2) 0.0585(5) Uani 1 1 d . . . . .
H10 H 0.8828 0.3054 0.5319 0.070 Uiso 1 1 calc R . . . .
C11 C 0.6627(4) 0.27880(6) 0.5450(3) 0.0726(7) Uani 1 1 d . . . . .
H11 H 0.7004 0.2613 0.6453 0.087 Uiso 1 1 calc R . . . .
C12 C 0.5016(3) 0.27766(6) 0.4680(3) 0.0658(6) Uani 1 1 d . . . . .
H12 H 0.4296 0.2594 0.5146 0.079 Uiso 1 1 calc R . . . .
C13 C 0.4458(2) 0.30369(5) 0.3207(2) 0.0503(4) Uani 1 1 d . . . . .
C14 C 0.2902(2) 0.30930(6) 0.2052(3) 0.0555(5) Uani 1 1 d . . . . .
C15 C 0.1327(3) 0.29164(8) 0.1977(4) 0.0810(8) Uani 1 1 d . . . . .
H15 H 0.1126 0.2711 0.2825 0.097 Uiso 1 1 calc R . . . .
C16 C 0.0091(3) 0.30509(10) 0.0634(4) 0.0946(10) Uani 1 1 d . . . . .
H16 H -0.0960 0.2937 0.0580 0.114 Uiso 1 1 calc R . . . .
C17 C 0.0356(3) 0.33454(10) -0.0613(4) 0.0870(8) Uani 1 1 d . . . . .
H17 H -0.0518 0.3430 -0.1504 0.104 Uiso 1 1 calc R . . . .
C18 C 0.1872(2) 0.35221(8) -0.0604(3) 0.0670(5) Uani 1 1 d . . . . .
H18 H 0.2050 0.3722 -0.1476 0.080 Uiso 1 1 calc R . . . .
C19 C 0.31325(19) 0.33921(6) 0.0754(2) 0.0490(4) Uani 1 1 d . . . . .
O3 O 0.70733(15) 0.53472(5) 0.52059(16) 0.0563(3) Uani 1 1 d . . . . .
H3 H 0.6301 0.5385 0.5659 0.084 Uiso 1 1 calc GR . . . .
C20 C 0.8265(2) 0.57143(7) 0.5784(3) 0.0654(5) Uani 1 1 d . . . . .
H20 H 0.7726 0.6032 0.5683 0.078 Uiso 1 1 calc R . . . .
C21 C 0.9071(3) 0.56235(10) 0.7608(3) 0.0782(7) Uani 1 1 d . . . . .
H21A H 0.8267 0.5629 0.8283 0.117 Uiso 1 1 calc GR . . . .
H21B H 0.9872 0.5871 0.8004 0.117 Uiso 1 1 calc GR . . . .
H21C H 0.9593 0.5312 0.7713 0.117 Uiso 1 1 calc GR . . . .
C22 C 0.9453(4) 0.57020(11) 0.4651(4) 0.0937(8) Uani 1 1 d . . . . .
H22A H 1.0062 0.5405 0.4835 0.141 Uiso 1 1 calc GR . . . .
H22B H 1.0189 0.5972 0.4917 0.141 Uiso 1 1 calc GR . . . .
H22C H 0.8869 0.5722 0.3477 0.141 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2082(19) . ?
O2 C1 1.3089(19) . ?
N1 C3 1.4203(19) . ?
N1 C8 1.384(2) . ?
N1 C19 1.395(2) . ?
C1 C2 1.496(2) . ?
C2 C3 1.399(2) . ?
C2 C7 1.398(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.382(2) . ?
C5 C6 1.375(3) . ?
C6 C7 1.381(2) . ?
C8 C9 1.381(2) . ?
C8 C13 1.414(2) . ?
C9 C10 1.388(2) . ?
C10 C11 1.403(3) . ?
C11 C12 1.368(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.443(3) . ?
C14 C15 1.415(3) . ?
C14 C19 1.392(3) . ?
C15 C16 1.380(4) . ?
C16 C17 1.362(4) . ?
C17 C18 1.378(3) . ?
C18 C19 1.397(3) . ?
O3 C20 1.440(2) . ?
C20 C21 1.502(3) . ?
C20 C22 1.515(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
C8 N1 C3 126.69(13) . . ?
C8 N1 C19 108.66(13) . . ?
C19 N1 C3 124.56(13) . . ?
O1 C1 O2 123.18(14) . . ?
O1 C1 C2 124.22(14) . . ?
O2 C1 C2 112.56(13) . . ?
C3 C2 C1 123.08(13) . . ?
C7 C2 C1 118.61(13) . . ?
C7 C2 C3 118.20(13) . . ?
C2 C3 N1 122.76(13) . . ?
C4 C3 N1 117.21(13) . . ?
C4 C3 C2 120.04(14) . . ?
C5 C4 C3 120.67(15) . . ?
C6 C5 C4 119.69(15) . . ?
C5 C6 C7 120.26(15) . . ?
C6 C7 C2 121.07(15) . . ?
N1 C8 C13 108.39(14) . . ?
C9 C8 N1 129.00(14) . . ?
C9 C8 C13 122.55(15) . . ?
C8 C9 C10 117.18(16) . . ?
C9 C10 C11 120.8(2) . . ?
C12 C11 C10 121.35(17) . . ?
C11 C12 C13 119.33(18) . . ?
C8 C13 C14 106.91(14) . . ?
C12 C13 C8 118.80(19) . . ?
C12 C13 C14 134.26(17) . . ?
C15 C14 C13 135.0(2) . . ?
C19 C14 C13 106.80(14) . . ?
C19 C14 C15 118.2(2) . . ?
C16 C15 C14 118.7(2) . . ?
C17 C16 C15 121.6(2) . . ?
C16 C17 C18 121.7(3) . . ?
C17 C18 C19 117.3(2) . . ?
N1 C19 C18 128.34(18) . . ?
C14 C19 N1 109.23(16) . . ?
C14 C19 C18 122.43(17) . . ?
O3 C20 C21 109.19(18) . . ?
O3 C20 C22 107.65(17) . . ?
C21 C20 C22 112.2(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.83 1.78 2.5965(17) 167.4 .
O3 H3 O1 0.83 1.96 2.7745(17) 164.9 3_666

_olex2_date_sample_data_collection 2017-04-20
_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 1.394
_oxdiff_exptl_absorpt_empirical_full_min 0.589
####################################################################### 
# 
# 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_exp_3497
_audit_block_doi                 10.5517/ccdc.csd.cc2pmfb3
_database_code_depnum_ccdc_archive 'CCDC 2491325'
loop_
_audit_author_name
_audit_author_address
'Yu Xiong'
;Shenzhen University
China
;
_audit_update_record             
;
2025-09-25 deposited with the CCDC.	2025-11-14 downloaded from the CCDC.
;
_audit_creation_date             2017-02-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H13 N O2, C H4 O'
_chemical_formula_sum            'C20 H17 N O3'
_chemical_formula_weight         319.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   8.1669(5)
_cell_length_b                   26.4699(16)
_cell_length_c                   15.7893(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.465(7)
_cell_angle_gamma                90
_cell_volume                     3305.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      27.0960
_cell_measurement_theta_min      3.0640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull light white'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16784
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.322
_diffrn_reflns_theta_min         2.773
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     14.00  52.00   1.00   15.00    --   16.81 -99.00 -30.00   38
  2  ω    -51.00  16.00   1.00   15.00    --   16.81 -57.00-150.00   67
  3  ω    -12.00  38.00   1.00   15.00    --   16.81 -19.00-150.00   50
  4  ω    -11.00  32.00   1.00   15.00    --   16.81 -99.00  60.00   43
  5  ω    -23.00  22.00   1.00   15.00    --  -17.43 -99.00-180.00   45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0391877000
_diffrn_orient_matrix_UB_12      -0.0223721000
_diffrn_orient_matrix_UB_13      -0.0100004000
_diffrn_orient_matrix_UB_21      -0.0368796000
_diffrn_orient_matrix_UB_22      0.0039073000
_diffrn_orient_matrix_UB_23      -0.0451942000
_diffrn_orient_matrix_UB_31      0.0718394000
_diffrn_orient_matrix_UB_32      0.0141862000
_diffrn_orient_matrix_UB_33      -0.0032458000
_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                5092
_reflns_number_total             7643
_reflns_odcompleteness_completeness 99.81
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     439
_refine_ls_number_reflns         7643
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.038
_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)+(0.0511P)²+0.3079P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1196
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00M(H00M), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S),
 C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y),
 C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014),
 C015(H015), C016(H016), C017(H017), C018(H018), C019(H019), C01A(H01A)
2.b Idealised Me refined as rotating group:
 C01B(H01b,H01c,H01d), C01C(H01e,H01f,H01g)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003), O005(H005), O006(H006)
;
_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
O001 O 0.25985(18) 0.49241(5) 0.69143(9) 0.0408(4) Uani 1 1 d . . . . .
O002 O -0.33299(18) 0.93557(6) 0.68309(10) 0.0408(4) Uani 1 1 d . . . . .
H002 H -0.2382 0.9476 0.6895 0.061 Uiso 1 1 calc GR . . . .
O003 O -0.3993(2) 0.61004(6) 0.40019(10) 0.0462(4) Uani 1 1 d . . . . .
H003 H -0.4815 0.6111 0.3579 0.069 Uiso 1 1 calc GR . . . .
O004 O -0.19001(18) 0.87682(5) 0.77123(11) 0.0473(4) Uani 1 1 d . . . . .
O005 O 0.5541(2) 0.47933(6) 0.81812(10) 0.0478(4) Uani 1 1 d . . . . .
H005 H 0.4712 0.4842 0.7773 0.072 Uiso 1 1 calc GR . . . .
O006 O 0.12058(19) 0.43883(6) 0.59127(10) 0.0496(4) Uani 1 1 d . . . . .
H006 H 0.2149 0.4263 0.5984 0.074 Uiso 1 1 calc GR . . . .
N007 N -0.3655(2) 0.78603(6) 0.76788(10) 0.0262(4) Uani 1 1 d . . . . .
N008 N 0.0807(2) 0.57597(6) 0.72234(10) 0.0280(4) Uani 1 1 d . . . . .
C009 C -0.1606(2) 0.73096(7) 0.75405(12) 0.0249(4) Uani 1 1 d . . . . .
C00A C -0.2711(2) 0.76873(7) 0.71148(12) 0.0248(4) Uani 1 1 d . . . . .
C00B C -0.3172(2) 0.75921(7) 0.84553(12) 0.0257(4) Uani 1 1 d . . . . .
C00C C -0.1899(2) 0.72479(7) 0.83959(12) 0.0259(4) Uani 1 1 d . . . . .
C00D C -0.5073(2) 0.81904(7) 0.74346(12) 0.0264(4) Uani 1 1 d . . . . .
C00E C -0.0602(2) 0.54622(7) 0.67870(12) 0.0274(4) Uani 1 1 d . . . . .
C00F C -0.0404(2) 0.49975(7) 0.64010(11) 0.0266(4) Uani 1 1 d . . . . .
C00G C 0.1889(2) 0.60246(7) 0.68392(13) 0.0273(4) Uani 1 1 d . . . . .
C00H C -0.2802(2) 0.78233(7) 0.62587(12) 0.0290(4) Uani 1 1 d . . . . .
H00H H -0.3533 0.8077 0.5983 0.035 Uiso 1 1 calc R . . . .
C00I C 0.1282(3) 0.47756(7) 0.64404(12) 0.0300(5) Uani 1 1 d . . . . .
C00J C -0.4901(2) 0.86913(7) 0.71925(12) 0.0270(4) Uani 1 1 d . . . . .
C00K C 0.1318(3) 0.58230(7) 0.81239(12) 0.0311(5) Uani 1 1 d . . . . .
C00L C -0.3225(3) 0.89318(7) 0.72739(12) 0.0302(5) Uani 1 1 d . . . . .
C00M C -0.0574(3) 0.70639(7) 0.70942(13) 0.0321(5) Uani 1 1 d . . . . .
H00M H 0.0175 0.6815 0.7370 0.039 Uiso 1 1 calc R . . . .
C00N C 0.3112(2) 0.62687(7) 0.74976(13) 0.0312(5) Uani 1 1 d . . . . .
C00O C 0.1838(3) 0.60732(7) 0.59631(13) 0.0320(5) Uani 1 1 d . . . . .
H00O H 0.1018 0.5911 0.5535 0.038 Uiso 1 1 calc R . . . .
C00P C -0.1866(3) 0.47293(8) 0.59988(12) 0.0323(5) Uani 1 1 d . . . . .
H00P H -0.1766 0.4422 0.5731 0.039 Uiso 1 1 calc R . . . .
C00Q C -0.3781(3) 0.76210(8) 0.91977(13) 0.0350(5) Uani 1 1 d . . . . .
H00Q H -0.4608 0.7854 0.9241 0.042 Uiso 1 1 calc R . . . .
C00R C 0.2740(3) 0.61449(7) 0.83213(13) 0.0330(5) Uani 1 1 d . . . . .
C00S C -0.0674(3) 0.71930(7) 0.62410(14) 0.0352(5) Uani 1 1 d . . . . .
H00S H 0.0001 0.7026 0.5935 0.042 Uiso 1 1 calc R . . . .
C00T C -0.1775(3) 0.75712(8) 0.58281(13) 0.0341(5) Uani 1 1 d . . . . .
H00T H -0.1816 0.7655 0.5251 0.041 Uiso 1 1 calc R . . . .
C00U C -0.3450(3) 0.49101(8) 0.59906(13) 0.0371(5) Uani 1 1 d . . . . .
H00U H -0.4405 0.4722 0.5728 0.044 Uiso 1 1 calc R . . . .
C00V C -0.2202(3) 0.56422(8) 0.67614(13) 0.0357(5) Uani 1 1 d . . . . .
H00V H -0.2322 0.5954 0.7012 0.043 Uiso 1 1 calc R . . . .
C00W C -0.6660(3) 0.79943(8) 0.73997(13) 0.0351(5) Uani 1 1 d . . . . .
H00W H -0.6765 0.7659 0.7556 0.042 Uiso 1 1 calc R . . . .
C00X C -0.1252(3) 0.69191(8) 0.90872(13) 0.0348(5) Uani 1 1 d . . . . .
H00X H -0.0407 0.6689 0.9057 0.042 Uiso 1 1 calc R . . . .
C00Y C -0.6368(3) 0.89771(8) 0.69017(13) 0.0346(5) Uani 1 1 d . . . . .
H00Y H -0.6284 0.9308 0.6719 0.042 Uiso 1 1 calc R . . . .
C00Z C -0.8086(3) 0.82901(8) 0.71353(14) 0.0391(5) Uani 1 1 d . . . . .
H00Z H -0.9144 0.8158 0.7131 0.047 Uiso 1 1 calc R . . . .
C010 C -0.7942(3) 0.87787(9) 0.68795(14) 0.0413(6) Uani 1 1 d . . . . .
H010 H -0.8904 0.8977 0.6691 0.050 Uiso 1 1 calc R . . . .
C011 C 0.0640(3) 0.56174(8) 0.87691(13) 0.0385(5) Uani 1 1 d . . . . .
H011 H -0.0285 0.5401 0.8631 0.046 Uiso 1 1 calc R . . . .
C012 C -0.3624(3) 0.53670(8) 0.63701(14) 0.0406(5) Uani 1 1 d . . . . .
H012 H -0.4693 0.5490 0.6363 0.049 Uiso 1 1 calc R . . . .
C013 C -0.3116(3) 0.72912(9) 0.98701(14) 0.0415(5) Uani 1 1 d . . . . .
H013 H -0.3503 0.7304 1.0376 0.050 Uiso 1 1 calc R . . . .
C014 C 0.3060(3) 0.63739(8) 0.57496(15) 0.0404(5) Uani 1 1 d . . . . .
H014 H 0.3063 0.6414 0.5165 0.049 Uiso 1 1 calc R . . . .
C015 C -0.1884(3) 0.69402(9) 0.98139(14) 0.0408(5) Uani 1 1 d . . . . .
H015 H -0.1483 0.6717 1.0274 0.049 Uiso 1 1 calc R . . . .
C016 C 0.3458(3) 0.62691(8) 0.91958(15) 0.0448(6) Uani 1 1 d . . . . .
H016 H 0.4385 0.6485 0.9344 0.054 Uiso 1 1 calc R . . . .
C017 C 0.4286(3) 0.66179(8) 0.63915(17) 0.0457(6) Uani 1 1 d . . . . .
H017 H 0.5091 0.6818 0.6228 0.055 Uiso 1 1 calc R . . . .
C018 C 0.4324(3) 0.65680(8) 0.72574(16) 0.0424(6) Uani 1 1 d . . . . .
H018 H 0.5149 0.6732 0.7681 0.051 Uiso 1 1 calc R . . . .
C019 C 0.1388(3) 0.57469(9) 0.96230(14) 0.0476(6) Uani 1 1 d . . . . .
H019 H 0.0957 0.5616 1.0070 0.057 Uiso 1 1 calc R . . . .
C01A C 0.2780(3) 0.60701(9) 0.98309(15) 0.0512(7) Uani 1 1 d . . . . .
H01A H 0.3256 0.6152 1.0413 0.061 Uiso 1 1 calc R . . . .
C01B C -0.3675(3) 0.65887(9) 0.43700(17) 0.0556(7) Uani 1 1 d . . . . .
H01B H -0.3069 0.6784 0.4036 0.083 Uiso 1 1 calc GR . . . .
H01C H -0.3011 0.6562 0.4963 0.083 Uiso 1 1 calc GR . . . .
H01D H -0.4729 0.6752 0.4361 0.083 Uiso 1 1 calc GR . . . .
C01C C 0.5646(4) 0.51740(11) 0.88031(18) 0.0738(9) Uani 1 1 d . . . . .
H01E H 0.5758 0.5495 0.8542 0.111 Uiso 1 1 calc GR . . . .
H01F H 0.6612 0.5116 0.9283 0.111 Uiso 1 1 calc GR . . . .
H01G H 0.4639 0.5173 0.9013 0.111 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00I 1.212(2) . ?
O002 H002 0.8200 . ?
O002 C00L 1.314(2) . ?
O003 H003 0.8200 . ?
O003 C01B 1.414(3) . ?
O004 C00L 1.210(2) . ?
O005 H005 0.8200 . ?
O005 C01C 1.395(3) . ?
O006 H006 0.8200 . ?
O006 C00I 1.313(2) . ?
N007 C00A 1.393(2) . ?
N007 C00B 1.386(2) . ?
N007 C00D 1.425(2) . ?
N008 C00E 1.422(2) . ?
N008 C00G 1.382(2) . ?
N008 C00K 1.388(2) . ?
C009 C00A 1.401(2) . ?
C009 C00C 1.439(3) . ?
C009 C00M 1.388(3) . ?
C00A C00H 1.383(3) . ?
C00B C00C 1.403(3) . ?
C00B C00Q 1.385(3) . ?
C00C C00X 1.393(3) . ?
C00D C00J 1.397(3) . ?
C00D C00W 1.384(3) . ?
C00E C00F 1.400(3) . ?
C00E C00V 1.382(3) . ?
C00F C00I 1.485(3) . ?
C00F C00P 1.398(3) . ?
C00G C00N 1.406(3) . ?
C00G C00O 1.380(3) . ?
C00H H00H 0.9300 . ?
C00H C00T 1.377(3) . ?
C00J C00L 1.485(3) . ?
C00J C00Y 1.394(3) . ?
C00K C00R 1.412(3) . ?
C00K C011 1.386(3) . ?
C00M H00M 0.9300 . ?
C00M C00S 1.372(3) . ?
C00N C00R 1.445(3) . ?
C00N C018 1.393(3) . ?
C00O H00O 0.9300 . ?
C00O C014 1.382(3) . ?
C00P H00P 0.9300 . ?
C00P C00U 1.377(3) . ?
C00Q H00Q 0.9300 . ?
C00Q C013 1.377(3) . ?
C00R C016 1.398(3) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.394(3) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C012 1.373(3) . ?
C00V H00V 0.9300 . ?
C00V C012 1.379(3) . ?
C00W H00W 0.9300 . ?
C00W C00Z 1.379(3) . ?
C00X H00X 0.9300 . ?
C00X C015 1.372(3) . ?
C00Y H00Y 0.9300 . ?
C00Y C010 1.381(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C010 1.369(3) . ?
C010 H010 0.9300 . ?
C011 H011 0.9300 . ?
C011 C019 1.377(3) . ?
C012 H012 0.9300 . ?
C013 H013 0.9300 . ?
C013 C015 1.388(3) . ?
C014 H014 0.9300 . ?
C014 C017 1.393(3) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C01A 1.366(3) . ?
C017 H017 0.9300 . ?
C017 C018 1.366(3) . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C019 C01A 1.395(3) . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9600 . ?
C01B H01C 0.9600 . ?
C01B H01D 0.9600 . ?
C01C H01E 0.9600 . ?
C01C H01F 0.9600 . ?
C01C H01G 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
C00L O002 H002 109.5 . . ?
C01B O003 H003 109.5 . . ?
C01C O005 H005 109.5 . . ?
C00I O006 H006 109.5 . . ?
C00A N007 C00D 124.81(15) . . ?
C00B N007 C00A 108.46(15) . . ?
C00B N007 C00D 125.86(16) . . ?
C00G N008 C00E 126.66(15) . . ?
C00G N008 C00K 109.07(16) . . ?
C00K N008 C00E 124.26(16) . . ?
C00A C009 C00C 107.04(16) . . ?
C00M C009 C00A 119.40(17) . . ?
C00M C009 C00C 133.48(18) . . ?
N007 C00A C009 108.73(15) . . ?
C00H C00A N007 129.51(17) . . ?
C00H C00A C009 121.71(17) . . ?
N007 C00B C00C 108.98(16) . . ?
C00Q C00B N007 129.60(18) . . ?
C00Q C00B C00C 121.42(17) . . ?
C00B C00C C009 106.79(16) . . ?
C00X C00C C009 133.42(18) . . ?
C00X C00C C00B 119.70(18) . . ?
C00J C00D N007 121.71(17) . . ?
C00W C00D N007 118.06(17) . . ?
C00W C00D C00J 120.15(18) . . ?
C00F C00E N008 122.03(17) . . ?
C00V C00E N008 117.89(17) . . ?
C00V C00E C00F 120.08(18) . . ?
C00E C00F C00I 122.42(17) . . ?
C00P C00F C00E 117.78(18) . . ?
C00P C00F C00I 119.75(17) . . ?
N008 C00G C00N 108.83(17) . . ?
C00O C00G N008 128.71(18) . . ?
C00O C00G C00N 122.44(18) . . ?
C00A C00H H00H 121.1 . . ?
C00T C00H C00A 117.76(18) . . ?
C00T C00H H00H 121.1 . . ?
O001 C00I O006 122.66(19) . . ?
O001 C00I C00F 124.63(18) . . ?
O006 C00I C00F 112.70(17) . . ?
C00D C00J C00L 122.46(18) . . ?
C00Y C00J C00D 117.92(18) . . ?
C00Y C00J C00L 119.56(18) . . ?
N008 C00K C00R 108.62(18) . . ?
C011 C00K N008 129.20(19) . . ?
C011 C00K C00R 122.17(19) . . ?
O002 C00L C00J 112.58(17) . . ?
O004 C00L O002 122.7(2) . . ?
O004 C00L C00J 124.69(19) . . ?
C009 C00M H00M 120.4 . . ?
C00S C00M C009 119.16(18) . . ?
C00S C00M H00M 120.4 . . ?
C00G C00N C00R 106.94(17) . . ?
C018 C00N C00G 118.81(19) . . ?
C018 C00N C00R 134.22(19) . . ?
C00G C00O H00O 121.4 . . ?
C00G C00O C014 117.10(19) . . ?
C014 C00O H00O 121.4 . . ?
C00F C00P H00P 119.3 . . ?
C00U C00P C00F 121.44(19) . . ?
C00U C00P H00P 119.3 . . ?
C00B C00Q H00Q 121.3 . . ?
C013 C00Q C00B 117.5(2) . . ?
C013 C00Q H00Q 121.3 . . ?
C00K C00R C00N 106.52(17) . . ?
C016 C00R C00K 118.6(2) . . ?
C016 C00R C00N 134.9(2) . . ?
C00M C00S H00S 119.6 . . ?
C00M C00S C00T 120.73(18) . . ?
C00T C00S H00S 119.6 . . ?
C00H C00T C00S 121.23(19) . . ?
C00H C00T H00T 119.4 . . ?
C00S C00T H00T 119.4 . . ?
C00P C00U H00U 120.0 . . ?
C012 C00U C00P 120.1(2) . . ?
C012 C00U H00U 120.0 . . ?
C00E C00V H00V 119.5 . . ?
C012 C00V C00E 121.0(2) . . ?
C012 C00V H00V 119.5 . . ?
C00D C00W H00W 119.6 . . ?
C00Z C00W C00D 120.7(2) . . ?
C00Z C00W H00W 119.6 . . ?
C00C C00X H00X 120.6 . . ?
C015 C00X C00C 118.8(2) . . ?
C015 C00X H00X 120.6 . . ?
C00J C00Y H00Y 119.3 . . ?
C010 C00Y C00J 121.3(2) . . ?
C010 C00Y H00Y 119.3 . . ?
C00W C00Z H00Z 120.1 . . ?
C010 C00Z C00W 119.8(2) . . ?
C010 C00Z H00Z 120.1 . . ?
C00Y C010 H010 120.0 . . ?
C00Z C010 C00Y 120.0(2) . . ?
C00Z C010 H010 120.0 . . ?
C00K C011 H011 121.3 . . ?
C019 C011 C00K 117.4(2) . . ?
C019 C011 H011 121.3 . . ?
C00U C012 C00V 119.6(2) . . ?
C00U C012 H012 120.2 . . ?
C00V C012 H012 120.2 . . ?
C00Q C013 H013 119.1 . . ?
C00Q C013 C015 121.8(2) . . ?
C015 C013 H013 119.1 . . ?
C00O C014 H014 119.3 . . ?
C00O C014 C017 121.4(2) . . ?
C017 C014 H014 119.3 . . ?
C00X C015 C013 120.7(2) . . ?
C00X C015 H015 119.6 . . ?
C013 C015 H015 119.6 . . ?
C00R C016 H016 120.4 . . ?
C01A C016 C00R 119.2(2) . . ?
C01A C016 H016 120.4 . . ?
C014 C017 H017 119.5 . . ?
C018 C017 C014 121.1(2) . . ?
C018 C017 H017 119.5 . . ?
C00N C018 H018 120.4 . . ?
C017 C018 C00N 119.2(2) . . ?
C017 C018 H018 120.4 . . ?
C011 C019 H019 119.4 . . ?
C011 C019 C01A 121.3(2) . . ?
C01A C019 H019 119.4 . . ?
C016 C01A C019 121.3(2) . . ?
C016 C01A H01A 119.3 . . ?
C019 C01A H01A 119.3 . . ?
O003 C01B H01B 109.5 . . ?
O003 C01B H01C 109.5 . . ?
O003 C01B H01D 109.5 . . ?
H01B C01B H01C 109.5 . . ?
H01B C01B H01D 109.5 . . ?
H01C C01B H01D 109.5 . . ?
O005 C01C H01E 109.5 . . ?
O005 C01C H01F 109.5 . . ?
O005 C01C H01G 109.5 . . ?
H01E C01C H01F 109.5 . . ?
H01E C01C H01G 109.5 . . ?
H01F C01C H01G 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.820
_oxdiff_exptl_absorpt_empirical_full_min 0.454
