# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_450_0m
_database_code_depnum_ccdc_archive 'CCDC 2301597'
loop_
_audit_author_name
_audit_author_address
'Hua Chen'
;Hebei university
China
;
_audit_update_record             
;
2023-10-17 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_weight         296.36
_chemical_absolute_configuration .
_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      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.4476(4)
_cell_length_b                   9.3390(8)
_cell_length_c                   15.3977(12)
_cell_angle_alpha                75.371(3)
_cell_angle_beta                 87.564(2)
_cell_angle_gamma                85.468(3)
_cell_volume                     755.39(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2190
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.853
_cell_measurement_theta_min      2.260
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5342
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1228 before and 0.0691 after correction.
The Ratio of minimum to maximum transmission is 0.7167.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8184
_diffrn_reflns_point_group_measured_fraction_full 0.807
_diffrn_reflns_point_group_measured_fraction_max 0.785
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.422
_diffrn_reflns_theta_min         2.259
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.608
_reflns_Friedel_fraction_full    0.630
_reflns_Friedel_fraction_max     0.594
_reflns_number_gt                3848
_reflns_number_total             4859
_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       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 
;
 Flack x determined using 1185 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         4859
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.060
_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)+(0.0416P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1120
_refine_ls_wR_factor_ref         0.1295
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N3-H3B = O3-H3A
 0.87 with sigma of 0.02
 N2-H2A
 0.87 with sigma of 0.02
 O4-H4A
 0.87 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C11(H11), C10(H10), C21(H21), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H1A), N4(H4B), C5(H5), C15(H15), C18(H18), C14(H14), C26(H26), C33(H33),
 C32(H32), C17(H17), C2(H2B), C3(H3), C28(H28), C35(H35), C34(H34), C36(H36),
 C16(H16), C4(H4), C27(H27), C30(H30)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C19(H19A,H19B,H19C)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_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
O2 O 0.6484(6) 0.2878(4) 0.5446(2) 0.0247(8) Uani 1 1 d . . . . .
H2 H 0.623024 0.376757 0.546635 0.037 Uiso 1 1 calc R U . . .
O3 O 0.5704(7) 0.5739(4) 0.5711(3) 0.0305(9) Uani 1 1 d D . . . .
O1 O 0.0729(6) 0.1295(3) 0.5127(2) 0.0231(8) Uani 1 1 d . . . . .
H1 H -0.053061 0.177498 0.526674 0.035 Uiso 1 1 calc R U . . .
N2 N 0.4988(8) 0.4036(5) 0.2208(3) 0.0188(9) Uani 1 1 d D . . . .
N1 N 0.0855(8) 0.1186(4) 0.3192(3) 0.0200(10) Uani 1 1 d . . . . .
H1A H 0.028088 0.049095 0.363471 0.024 Uiso 1 1 calc R U . . .
O4 O 0.8727(9) 0.8316(5) 0.3886(3) 0.0421(11) Uani 1 1 d D . . . .
N4 N 0.9845(8) 0.8793(5) 0.6733(3) 0.0237(10) Uani 1 1 d . . . . .
H4B H 1.057378 0.944525 0.630584 0.028 Uiso 1 1 calc R U . . .
N3 N 0.5351(8) 0.6084(4) 0.7547(3) 0.0225(10) Uani 1 1 d D . . . .
C13 C 0.4332(9) 0.5553(5) 0.1906(3) 0.0183(11) Uani 1 1 d . . . . .
C31 C 0.5829(9) 0.4567(5) 0.7998(3) 0.0182(11) Uani 1 1 d . . . . .
C8 C 0.2767(9) 0.2046(5) 0.3256(3) 0.0197(11) Uani 1 1 d . . . . .
C29 C 1.0416(9) 0.8433(5) 0.7632(3) 0.0198(12) Uani 1 1 d . . . . .
C24 C 0.7297(9) 0.7056(5) 0.7425(3) 0.0200(11) Uani 1 1 d . . . . .
C5 C 0.0949(9) 0.3323(5) 0.0917(3) 0.0201(11) Uani 1 1 d . . . . .
H5 H 0.189806 0.408197 0.056590 0.024 Uiso 1 1 calc R U . . .
C15 C 0.5486(10) 0.8001(6) 0.1114(3) 0.0238(12) Uani 1 1 d . . . . .
H15 H 0.664198 0.861943 0.075500 0.029 Uiso 1 1 calc R U . . .
C18 C 0.2109(9) 0.6178(5) 0.2155(3) 0.0215(12) Uani 1 1 d . . . . .
H18 H 0.092952 0.556771 0.250532 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4253(9) 0.2128(5) 0.5695(3) 0.0199(11) Uani 1 1 d . . . . .
H11 H 0.472242 0.105167 0.595377 0.024 Uiso 1 1 calc R U . . .
C14 C 0.6013(9) 0.6469(5) 0.1370(3) 0.0190(11) Uani 1 1 d . . . . .
H14 H 0.751923 0.604616 0.117842 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4171(9) 0.1835(5) 0.4095(3) 0.0208(11) Uani 1 1 d . . . . .
H9A H 0.562326 0.243415 0.395632 0.025 Uiso 1 1 calc R U . . .
H9B H 0.478290 0.078013 0.429334 0.025 Uiso 1 1 calc R U . . .
C26 C 0.9044(10) 0.6802(5) 0.9019(3) 0.0216(12) Uani 1 1 d . . . . .
H26 H 0.798667 0.607945 0.934305 0.026 Uiso 1 1 calc R U . . .
C33 C 0.4055(9) 0.3815(5) 0.8572(3) 0.0210(12) Uani 1 1 d . . . . .
H33 H 0.259183 0.434153 0.871363 0.025 Uiso 1 1 calc R U . . .
C7 C 0.3156(9) 0.3001(5) 0.2428(3) 0.0184(11) Uani 1 1 d . . . . .
C32 C 0.4414(10) 0.2297(6) 0.8939(3) 0.0231(12) Uani 1 1 d . . . . .
H32 H 0.318190 0.178848 0.932507 0.028 Uiso 1 1 calc R U . . .
C17 C 0.1617(10) 0.7709(6) 0.1886(4) 0.0246(12) Uani 1 1 d . . . . .
H17 H 0.008339 0.813002 0.205575 0.029 Uiso 1 1 calc R U . . .
C2 C -0.1911(9) 0.1047(5) 0.1949(3) 0.0196(11) Uani 1 1 d . . . . .
H2B H -0.287731 0.029106 0.229320 0.023 Uiso 1 1 calc R U . . .
C10 C 0.2698(9) 0.2262(5) 0.4870(3) 0.0184(11) Uani 1 1 d . . . . .
H10 H 0.198439 0.330756 0.466240 0.022 Uiso 1 1 calc R U . . .
C6 C 0.1407(9) 0.2727(5) 0.1830(3) 0.0173(11) Uani 1 1 d . . . . .
C3 C -0.2327(10) 0.1663(5) 0.1051(4) 0.0231(12) Uani 1 1 d . . . . .
H3 H -0.360580 0.132002 0.077206 0.028 Uiso 1 1 calc R U . . .
C25 C 0.8845(9) 0.7343(5) 0.8093(3) 0.0204(12) Uani 1 1 d . . . . .
C1 C -0.0013(9) 0.1580(5) 0.2330(3) 0.0178(11) Uani 1 1 d . . . . .
C28 C 1.2347(10) 0.8393(6) 0.8990(4) 0.0230(12) Uani 1 1 d . . . . .
H28 H 1.354238 0.873288 0.930833 0.028 Uiso 1 1 calc R U . . .
C23 C 0.7954(9) 0.7971(5) 0.6611(3) 0.0207(12) Uani 1 1 d . . . . .
C35 C 0.8339(10) 0.2281(5) 0.8195(3) 0.0229(12) Uani 1 1 d . . . . .
H35 H 0.982857 0.175731 0.807382 0.027 Uiso 1 1 calc R U . . .
C34 C 0.8003(9) 0.3792(5) 0.7814(3) 0.0198(11) Uani 1 1 d . . . . .
H34 H 0.924286 0.429608 0.743018 0.024 Uiso 1 1 calc R U . . .
C36 C 0.6552(10) 0.1518(6) 0.8748(4) 0.0228(12) Uani 1 1 d . . . . .
H36 H 0.678757 0.047773 0.899302 0.027 Uiso 1 1 calc R U . . .
C16 C 0.3271(10) 0.8629(6) 0.1384(4) 0.0267(12) Uani 1 1 d . . . . .
H16 H 0.291642 0.967353 0.122340 0.032 Uiso 1 1 calc R U . . .
C4 C -0.0919(9) 0.2781(6) 0.0538(3) 0.0233(12) Uani 1 1 d . . . . .
H4 H -0.125179 0.317377 -0.008098 0.028 Uiso 1 1 calc R U . . .
C21 C 0.7341(10) 0.6857(5) 0.5297(3) 0.0258(12) Uani 1 1 d . . . . .
H21 H 0.908116 0.643265 0.539057 0.031 Uiso 1 1 calc R U . . .
C27 C 1.0787(10) 0.7323(6) 0.9461(3) 0.0238(12) Uani 1 1 d . . . . .
H27 H 1.093227 0.695300 1.009236 0.029 Uiso 1 1 calc R U . . .
C30 C 1.2186(10) 0.8962(5) 0.8078(4) 0.0235(12) Uani 1 1 d . . . . .
H30 H 1.324302 0.969077 0.776147 0.028 Uiso 1 1 calc R U . . .
C22 C 0.6945(10) 0.8196(5) 0.5699(3) 0.0235(12) Uani 1 1 d . . . . .
H22A H 0.771557 0.904520 0.528965 0.028 Uiso 1 1 calc R U . . .
H22B H 0.515464 0.846568 0.572870 0.028 Uiso 1 1 calc R U . . .
C12 C 0.2794(9) 0.2716(6) 0.6409(3) 0.0240(11) Uani 1 1 d . . . . .
H12A H 0.228492 0.376747 0.616694 0.036 Uiso 1 1 calc R U . . .
H12B H 0.382387 0.260674 0.693204 0.036 Uiso 1 1 calc R U . . .
H12C H 0.133182 0.215505 0.659035 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6848(11) 0.7317(6) 0.4295(3) 0.0294(13) Uani 1 1 d . . . . .
H20 H 0.519927 0.787772 0.420199 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6885(12) 0.6042(6) 0.3860(4) 0.0368(15) Uani 1 1 d . . . . .
H19A H 0.846394 0.545519 0.397061 0.055 Uiso 1 1 calc R U . . .
H19B H 0.667248 0.642642 0.321211 0.055 Uiso 1 1 calc R U . . .
H19C H 0.554124 0.541426 0.411488 0.055 Uiso 1 1 calc R U . . .
H3B H 0.395(6) 0.645(5) 0.774(4) 0.030(16) Uiso 1 1 d D . . . .
H3A H 0.546(16) 0.583(9) 0.626(3) 0.10(3) Uiso 1 1 d D . . . .
H2A H 0.639(6) 0.380(6) 0.196(3) 0.031(16) Uiso 1 1 d D . . . .
H4A H 0.986(14) 0.793(10) 0.358(7) 0.15(5) 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
O2 H2 0.8400 . ?
O2 C11 1.440(5) . ?
O3 C21 1.433(6) . ?
O3 H3A 0.87(3) . ?
O1 H1 0.8400 . ?
O1 C10 1.435(5) . ?
N2 C13 1.397(6) . ?
N2 C7 1.416(6) . ?
N2 H2A 0.87(2) . ?
N1 H1A 0.8800 . ?
N1 C8 1.386(6) . ?
N1 C1 1.378(6) . ?
O4 C20 1.454(6) . ?
O4 H4A 0.87(3) . ?
N4 H4B 0.8800 . ?
N4 C29 1.382(6) . ?
N4 C23 1.379(6) . ?
N3 C31 1.420(6) . ?
N3 C24 1.425(6) . ?
N3 H3B 0.89(2) . ?
C13 C18 1.384(7) . ?
C13 C14 1.398(7) . ?
C31 C33 1.389(7) . ?
C31 C34 1.395(7) . ?
C8 C9 1.491(7) . ?
C8 C7 1.378(7) . ?
C29 C25 1.412(7) . ?
C29 C30 1.396(7) . ?
C24 C25 1.446(7) . ?
C24 C23 1.379(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.400(7) . ?
C5 C4 1.383(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.395(7) . ?
C15 C16 1.393(7) . ?
C18 H18 0.9500 . ?
C18 C17 1.392(7) . ?
C11 H11 1.0000 . ?
C11 C10 1.530(6) . ?
C11 C12 1.519(6) . ?
C14 H14 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(6) . ?
C26 H26 0.9500 . ?
C26 C25 1.393(7) . ?
C26 C27 1.377(7) . ?
C33 H33 0.9500 . ?
C33 C32 1.389(7) . ?
C7 C6 1.433(7) . ?
C32 H32 0.9500 . ?
C32 C36 1.385(7) . ?
C17 H17 0.9500 . ?
C17 C16 1.369(7) . ?
C2 H2B 0.9500 . ?
C2 C3 1.377(7) . ?
C2 C1 1.394(7) . ?
C10 H10 1.0000 . ?
C6 C1 1.415(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(7) . ?
C28 H28 0.9500 . ?
C28 C27 1.401(8) . ?
C28 C30 1.375(7) . ?
C23 C22 1.488(7) . ?
C35 H35 0.9500 . ?
C35 C34 1.385(7) . ?
C35 C36 1.383(7) . ?
C34 H34 0.9500 . ?
C36 H36 0.9500 . ?
C16 H16 0.9500 . ?
C4 H4 0.9500 . ?
C21 H21 1.0000 . ?
C21 C22 1.527(7) . ?
C21 C20 1.523(7) . ?
C27 H27 0.9500 . ?
C30 H30 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C20 H20 1.0000 . ?
C20 C19 1.505(7) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 H2 109.5 . . ?
C21 O3 H3A 105(5) . . ?
C10 O1 H1 109.5 . . ?
C13 N2 C7 120.6(4) . . ?
C13 N2 H2A 111(4) . . ?
C7 N2 H2A 120(4) . . ?
C8 N1 H1A 125.1 . . ?
C1 N1 H1A 125.1 . . ?
C1 N1 C8 109.9(4) . . ?
C20 O4 H4A 114(6) . . ?
C29 N4 H4B 125.4 . . ?
C23 N4 H4B 125.4 . . ?
C23 N4 C29 109.3(4) . . ?
C31 N3 C24 119.1(4) . . ?
C31 N3 H3B 111(4) . . ?
C24 N3 H3B 114(3) . . ?
N2 C13 C14 119.0(5) . . ?
C18 C13 N2 121.7(5) . . ?
C18 C13 C14 119.3(5) . . ?
C33 C31 N3 120.2(4) . . ?
C33 C31 C34 119.4(5) . . ?
C34 C31 N3 120.2(5) . . ?
N1 C8 C9 122.7(4) . . ?
C7 C8 N1 108.5(4) . . ?
C7 C8 C9 128.7(5) . . ?
N4 C29 C25 107.9(4) . . ?
N4 C29 C30 130.4(5) . . ?
C30 C29 C25 121.7(5) . . ?
N3 C24 C25 128.7(5) . . ?
C23 C24 N3 124.1(5) . . ?
C23 C24 C25 107.1(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.5(5) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C16 C15 C14 120.3(5) . . ?
C13 C18 H18 120.3 . . ?
C13 C18 C17 119.4(5) . . ?
C17 C18 H18 120.3 . . ?
O2 C11 H11 108.0 . . ?
O2 C11 C10 110.7(4) . . ?
O2 C11 C12 111.0(4) . . ?
C10 C11 H11 108.0 . . ?
C12 C11 H11 108.0 . . ?
C12 C11 C10 111.1(4) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(5) . . ?
C15 C14 H14 119.9 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.7(4) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 H26 120.3 . . ?
C27 C26 C25 119.4(5) . . ?
C31 C33 H33 119.9 . . ?
C31 C33 C32 120.3(5) . . ?
C32 C33 H33 119.9 . . ?
N2 C7 C6 126.5(5) . . ?
C8 C7 N2 126.0(5) . . ?
C8 C7 C6 107.4(4) . . ?
C33 C32 H32 119.7 . . ?
C36 C32 C33 120.5(5) . . ?
C36 C32 H32 119.7 . . ?
C18 C17 H17 118.9 . . ?
C16 C17 C18 122.1(5) . . ?
C16 C17 H17 118.9 . . ?
C3 C2 H2B 121.4 . . ?
C3 C2 C1 117.2(5) . . ?
C1 C2 H2B 121.4 . . ?
O1 C10 C11 108.3(4) . . ?
O1 C10 C9 108.5(3) . . ?
O1 C10 H10 109.0 . . ?
C11 C10 H10 109.0 . . ?
C9 C10 C11 112.9(4) . . ?
C9 C10 H10 109.0 . . ?
C5 C6 C7 133.5(5) . . ?
C5 C6 C1 119.4(4) . . ?
C1 C6 C7 107.1(4) . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(5) . . ?
C4 C3 H3 119.1 . . ?
C29 C25 C24 106.4(4) . . ?
C26 C25 C29 119.0(5) . . ?
C26 C25 C24 134.5(5) . . ?
N1 C1 C2 130.8(5) . . ?
N1 C1 C6 107.2(4) . . ?
C2 C1 C6 122.0(5) . . ?
C27 C28 H28 119.3 . . ?
C30 C28 H28 119.3 . . ?
C30 C28 C27 121.4(5) . . ?
N4 C23 C22 119.6(5) . . ?
C24 C23 N4 109.2(5) . . ?
C24 C23 C22 131.1(5) . . ?
C34 C35 H35 119.3 . . ?
C36 C35 H35 119.3 . . ?
C36 C35 C34 121.4(5) . . ?
C31 C34 H34 120.3 . . ?
C35 C34 C31 119.5(5) . . ?
C35 C34 H34 120.3 . . ?
C32 C36 H36 120.5 . . ?
C35 C36 C32 118.9(5) . . ?
C35 C36 H36 120.5 . . ?
C15 C16 H16 120.7 . . ?
C17 C16 C15 118.6(5) . . ?
C17 C16 H16 120.7 . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
O3 C21 H21 109.2 . . ?
O3 C21 C22 110.9(4) . . ?
O3 C21 C20 108.0(4) . . ?
C22 C21 H21 109.2 . . ?
C20 C21 H21 109.2 . . ?
C20 C21 C22 110.3(4) . . ?
C26 C27 C28 120.7(5) . . ?
C26 C27 H27 119.6 . . ?
C28 C27 H27 119.6 . . ?
C29 C30 H30 121.1 . . ?
C28 C30 C29 117.7(5) . . ?
C28 C30 H30 121.1 . . ?
C23 C22 C21 115.0(4) . . ?
C23 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C21 C22 H22A 108.5 . . ?
C21 C22 H22B 108.5 . . ?
H22A C22 H22B 107.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C20 C21 106.3(4) . . ?
O4 C20 H20 108.6 . . ?
O4 C20 C19 110.4(4) . . ?
C21 C20 H20 108.6 . . ?
C19 C20 C21 114.2(4) . . ?
C19 C20 H20 108.6 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C11 C10 O1 170.3(4) . . . . ?
O2 C11 C10 C9 50.1(5) . . . . ?
O3 C21 C22 C23 74.9(6) . . . . ?
O3 C21 C20 O4 -173.4(4) . . . . ?
O3 C21 C20 C19 -51.5(6) . . . . ?
N2 C13 C18 C17 175.6(4) . . . . ?
N2 C13 C14 C15 -175.2(4) . . . . ?
N2 C7 C6 C5 0.0(9) . . . . ?
N2 C7 C6 C1 178.5(4) . . . . ?
N1 C8 C9 C10 -68.6(6) . . . . ?
N1 C8 C7 N2 -178.3(4) . . . . ?
N1 C8 C7 C6 0.4(5) . . . . ?
N4 C29 C25 C24 0.2(5) . . . . ?
N4 C29 C25 C26 -179.4(4) . . . . ?
N4 C29 C30 C28 -179.9(5) . . . . ?
N4 C23 C22 C21 115.3(5) . . . . ?
N3 C31 C33 C32 173.3(4) . . . . ?
N3 C31 C34 C35 -174.0(4) . . . . ?
N3 C24 C25 C29 -177.8(5) . . . . ?
N3 C24 C25 C26 1.8(9) . . . . ?
N3 C24 C23 N4 178.1(4) . . . . ?
N3 C24 C23 C22 -0.4(8) . . . . ?
C13 N2 C7 C8 -119.4(6) . . . . ?
C13 N2 C7 C6 62.2(6) . . . . ?
C13 C18 C17 C16 -0.4(8) . . . . ?
C31 N3 C24 C25 -54.9(7) . . . . ?
C31 N3 C24 C23 128.5(5) . . . . ?
C31 C33 C32 C36 0.9(7) . . . . ?
C8 N1 C1 C2 -179.2(5) . . . . ?
C8 N1 C1 C6 0.3(5) . . . . ?
C8 C9 C10 O1 63.8(5) . . . . ?
C8 C9 C10 C11 -176.1(4) . . . . ?
C8 C7 C6 C5 -178.7(5) . . . . ?
C8 C7 C6 C1 -0.2(6) . . . . ?
C29 N4 C23 C24 -0.7(5) . . . . ?
C29 N4 C23 C22 178.0(4) . . . . ?
C24 N3 C31 C33 142.6(5) . . . . ?
C24 N3 C31 C34 -42.4(7) . . . . ?
C24 C23 C22 C21 -66.3(7) . . . . ?
C5 C6 C1 N1 178.7(4) . . . . ?
C5 C6 C1 C2 -1.8(7) . . . . ?
C18 C13 C14 C15 2.2(7) . . . . ?
C18 C17 C16 C15 1.9(8) . . . . ?
C14 C13 C18 C17 -1.7(7) . . . . ?
C14 C15 C16 C17 -1.4(8) . . . . ?
C9 C8 C7 N2 -2.0(9) . . . . ?
C9 C8 C7 C6 176.8(5) . . . . ?
C33 C31 C34 C35 1.1(7) . . . . ?
C33 C32 C36 C35 0.9(8) . . . . ?
C7 N2 C13 C18 28.1(7) . . . . ?
C7 N2 C13 C14 -154.6(4) . . . . ?
C7 C8 C9 C10 115.5(6) . . . . ?
C7 C6 C1 N1 0.0(5) . . . . ?
C7 C6 C1 C2 179.5(4) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C3 C2 C1 N1 -179.3(5) . . . . ?
C3 C2 C1 C6 1.3(7) . . . . ?
C25 C29 C30 C28 -0.5(7) . . . . ?
C25 C24 C23 N4 0.9(5) . . . . ?
C25 C24 C23 C22 -177.7(5) . . . . ?
C25 C26 C27 C28 0.3(8) . . . . ?
C1 N1 C8 C9 -177.1(4) . . . . ?
C1 N1 C8 C7 -0.4(5) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
C23 N4 C29 C25 0.3(6) . . . . ?
C23 N4 C29 C30 179.8(5) . . . . ?
C23 C24 C25 C29 -0.7(5) . . . . ?
C23 C24 C25 C26 178.9(6) . . . . ?
C34 C31 C33 C32 -1.8(7) . . . . ?
C34 C35 C36 C32 -1.6(8) . . . . ?
C36 C35 C34 C31 0.7(8) . . . . ?
C16 C15 C14 C13 -0.7(7) . . . . ?
C4 C5 C6 C7 179.4(5) . . . . ?
C4 C5 C6 C1 1.0(7) . . . . ?
C27 C26 C25 C29 -1.0(7) . . . . ?
C27 C26 C25 C24 179.5(5) . . . . ?
C27 C28 C30 C29 -0.3(8) . . . . ?
C30 C29 C25 C24 -179.3(4) . . . . ?
C30 C29 C25 C26 1.1(7) . . . . ?
C30 C28 C27 C26 0.4(8) . . . . ?
C22 C21 C20 O4 65.3(5) . . . . ?
C22 C21 C20 C19 -172.8(5) . . . . ?
C12 C11 C10 O1 -65.9(5) . . . . ?
C12 C11 C10 C9 173.9(4) . . . . ?
C20 C21 C22 C23 -165.6(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_d1583_0m
_database_code_depnum_ccdc_archive 'CCDC 2303074'
loop_
_audit_author_name
_audit_author_address
Chen
;Hebei University
China
;
_audit_update_record             
;
2023-10-24 deposited with the CCDC.	2024-01-30 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N O2'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_chemical_absolute_configuration Unk
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.163(2)
_cell_length_b                   10.528(4)
_cell_length_c                   32.488(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2108.0(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7460
_cell_measurement_temperature    273
_cell_measurement_theta_max      21.799
_cell_measurement_theta_min      2.305
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1257 before and 0.0694 after correction.
The Ratio of minimum to maximum transmission is 0.8903.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            36350
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.717
_diffrn_reflns_theta_min         2.033
_diffrn_ambient_temperature      273
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2936
_reflns_number_total             4863
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.290
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4863
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1167
_refine_ls_R_factor_gt           0.0600
_refine_ls_restrained_S_all      1.091
_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)+(0.0559P)²+0.6442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1568
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C17(H17), C19(H19), C20(H20)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C9(H9A,H9B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C11(H11), C12(H12), C15(H15), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2161(4) 0.5826(3) 0.20569(9) 0.0590(8) Uani 1 1 d . . . . .
O2 O 0.5079(6) 0.5332(4) 0.27515(10) 0.0886(12) Uani 1 1 d . . . . .
O3 O 0.7197(5) 0.5473(3) 0.36118(10) 0.0670(9) Uani 1 1 d . . . . .
O4 O 1.0028(6) 0.5058(4) 0.28975(9) 0.0789(11) Uani 1 1 d . . . . .
N1 N 0.7480(6) 0.5858(4) 0.17145(11) 0.0667(10) Uani 1 1 d . . . . .
N2 N 1.2552(6) 0.5756(4) 0.39123(11) 0.0613(10) Uani 1 1 d . . . . .
C1 C 0.1902(10) 0.7394(5) 0.04013(14) 0.0802(16) Uani 1 1 d . . . . .
H1A H 0.268525 0.734570 0.014646 0.120 Uiso 1 1 calc R U . . .
H1B H 0.143151 0.825189 0.044652 0.120 Uiso 1 1 calc R U . . .
H1C H 0.066068 0.684395 0.038912 0.120 Uiso 1 1 calc R U . . .
C2 C 0.3352(8) 0.6987(4) 0.07485(13) 0.0587(11) Uani 1 1 d . . . . .
C3 C 0.2652(7) 0.6181(4) 0.10570(12) 0.0530(10) Uani 1 1 d . . . . .
H3 H 0.124839 0.586042 0.104237 0.064 Uiso 1 1 calc R U . . .
C4 C 0.3946(6) 0.5827(4) 0.13881(12) 0.0465(9) Uani 1 1 d . . . . .
C5 C 0.3109(7) 0.5038(4) 0.17344(12) 0.0517(10) Uani 1 1 d . . . . .
H5 H 0.198072 0.447154 0.162740 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3685(7) 0.6702(4) 0.22285(13) 0.0594(11) Uani 1 1 d . . . . .
H6A H 0.299893 0.716819 0.245079 0.071 Uiso 1 1 calc R U . . .
H6B H 0.411308 0.730917 0.201901 0.071 Uiso 1 1 calc R U . . .
C7 C 0.5679(7) 0.6036(5) 0.23908(13) 0.0635(12) Uani 1 1 d . . . . .
H7 H 0.676954 0.667230 0.246582 0.076 Uiso 1 1 calc R U . . .
C8 C 0.6623(7) 0.5156(5) 0.20640(14) 0.0614(12) Uani 1 1 d . . . . .
H8 H 0.780656 0.466647 0.218790 0.074 Uiso 1 1 calc R U . . .
C9 C 0.4884(7) 0.4239(5) 0.19195(14) 0.0634(12) Uani 1 1 d . . . . .
H9A H 0.546919 0.365836 0.171582 0.076 Uiso 1 1 calc R U . . .
H9B H 0.433088 0.374743 0.214925 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6097(7) 0.6242(4) 0.14025(13) 0.0528(10) Uani 1 1 d . . . . .
C11 C 0.6809(8) 0.7061(5) 0.10907(14) 0.0642(13) Uani 1 1 d . . . . .
H11 H 0.822051 0.737194 0.109874 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5480(9) 0.7413(4) 0.07766(14) 0.0666(13) Uani 1 1 d . . . . .
H12 H 0.601171 0.795534 0.057447 0.080 Uiso 1 1 calc R U . . .
C13 C 0.7288(10) 0.6027(5) 0.53558(16) 0.0868(17) Uani 1 1 d . . . . .
H13A H 0.597080 0.647903 0.529717 0.130 Uiso 1 1 calc R U . . .
H13B H 0.807197 0.646035 0.556903 0.130 Uiso 1 1 calc R U . . .
H13C H 0.694431 0.518146 0.544524 0.130 Uiso 1 1 calc R U . . .
C14 C 0.8665(8) 0.5964(4) 0.49723(15) 0.0606(12) Uani 1 1 d . . . . .
C15 C 0.7883(8) 0.6308(4) 0.45869(16) 0.0619(12) Uani 1 1 d . . . . .
H15 H 0.647269 0.661593 0.456718 0.074 Uiso 1 1 calc R U . . .
C16 C 0.9110(7) 0.6212(4) 0.42297(14) 0.0543(10) Uani 1 1 d . . . . .
C17 C 0.8205(8) 0.6558(4) 0.38190(15) 0.0638(13) Uani 1 1 d . . . . .
H17 H 0.711183 0.722453 0.385589 0.077 Uiso 1 1 calc R U . . .
C18 C 0.8672(7) 0.4444(4) 0.35527(15) 0.0618(11) Uani 1 1 d . . . . .
H18A H 0.793820 0.376640 0.340567 0.074 Uiso 1 1 calc R U . . .
H18B H 0.910780 0.411491 0.381910 0.074 Uiso 1 1 calc R U . . .
C19 C 1.0663(7) 0.4830(5) 0.33157(13) 0.0614(12) Uani 1 1 d . . . . .
H19 H 1.171985 0.413457 0.332267 0.074 Uiso 1 1 calc R U . . .
C20 C 1.1685(7) 0.6022(4) 0.35081(15) 0.0608(12) Uani 1 1 d . . . . .
H20 H 1.286525 0.631815 0.333007 0.073 Uiso 1 1 calc R U . . .
C21 C 0.9983(8) 0.7055(5) 0.35380(16) 0.0685(13) Uani 1 1 d . . . . .
H21A H 0.939971 0.724619 0.326772 0.082 Uiso 1 1 calc R U . . .
H21B H 1.061148 0.782459 0.365127 0.082 Uiso 1 1 calc R U . . .
C22 C 1.1248(7) 0.5797(4) 0.42572(14) 0.0531(10) Uani 1 1 d . . . . .
C23 C 1.2053(7) 0.5459(4) 0.46463(14) 0.0608(12) Uani 1 1 d . . . . .
H23 H 1.347165 0.516883 0.467099 0.073 Uiso 1 1 calc R U . . .
C24 C 1.0777(8) 0.5551(4) 0.49902(15) 0.0647(12) Uani 1 1 d . . . . .
H24 H 1.135893 0.532676 0.524410 0.078 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.458(5) . ?
O1 C6 1.430(5) . ?
O2 C7 1.435(6) . ?
O3 C17 1.464(6) . ?
O3 C18 1.428(5) . ?
O4 C19 1.434(5) . ?
N1 C8 1.454(6) . ?
N1 C10 1.384(5) . ?
N2 C20 1.445(6) . ?
N2 C22 1.379(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.502(6) . ?
C2 C3 1.382(6) . ?
C2 C12 1.389(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(6) . ?
C4 C5 1.491(6) . ?
C4 C10 1.397(6) . ?
C5 H5 0.9800 . ?
C5 C9 1.506(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.510(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.524(6) . ?
C8 H8 0.9800 . ?
C8 C9 1.517(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.401(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(7) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C13 C14 1.509(6) . ?
C14 C15 1.390(7) . ?
C14 C24 1.374(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.388(6) . ?
C16 C17 1.492(6) . ?
C16 C22 1.392(6) . ?
C17 H17 0.9800 . ?
C17 C21 1.520(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.505(6) . ?
C19 H19 0.9800 . ?
C19 C20 1.537(6) . ?
C20 H20 0.9800 . ?
C20 C21 1.514(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.403(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.370(7) . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C5 112.6(3) . . ?
C18 O3 C17 112.6(3) . . ?
C10 N1 C8 119.8(4) . . ?
C22 N2 C20 121.1(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
C3 C2 C1 122.3(5) . . ?
C3 C2 C12 116.4(4) . . ?
C12 C2 C1 121.3(4) . . ?
C2 C3 H3 118.4 . . ?
C2 C3 C4 123.2(4) . . ?
C4 C3 H3 118.4 . . ?
C3 C4 C5 122.4(4) . . ?
C3 C4 C10 119.1(4) . . ?
C10 C4 C5 118.5(4) . . ?
O1 C5 C4 111.4(3) . . ?
O1 C5 H5 108.5 . . ?
O1 C5 C9 108.8(3) . . ?
C4 C5 H5 108.5 . . ?
C4 C5 C9 111.2(4) . . ?
C9 C5 H5 108.5 . . ?
O1 C6 H6A 109.3 . . ?
O1 C6 H6B 109.3 . . ?
O1 C6 C7 111.8(4) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
O2 C7 C6 108.4(4) . . ?
O2 C7 H7 109.1 . . ?
O2 C7 C8 110.7(4) . . ?
C6 C7 H7 109.1 . . ?
C6 C7 C8 110.5(4) . . ?
C8 C7 H7 109.1 . . ?
N1 C8 C7 112.0(4) . . ?
N1 C8 H8 108.5 . . ?
N1 C8 C9 109.8(4) . . ?
C7 C8 H8 108.5 . . ?
C9 C8 C7 109.4(4) . . ?
C9 C8 H8 108.5 . . ?
C5 C9 C8 106.3(4) . . ?
C5 C9 H9A 110.5 . . ?
C5 C9 H9B 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
N1 C10 C4 121.2(4) . . ?
N1 C10 C11 121.1(4) . . ?
C4 C10 C11 117.7(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C2 C12 H12 119.0 . . ?
C11 C12 C2 122.0(4) . . ?
C11 C12 H12 119.0 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
C15 C14 C13 122.5(5) . . ?
C24 C14 C13 120.8(5) . . ?
C24 C14 C15 116.7(4) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 C14 123.0(4) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C17 121.7(4) . . ?
C15 C16 C22 119.0(4) . . ?
C22 C16 C17 119.2(4) . . ?
O3 C17 C16 112.3(4) . . ?
O3 C17 H17 108.8 . . ?
O3 C17 C21 107.4(4) . . ?
C16 C17 H17 108.8 . . ?
C16 C17 C21 110.6(4) . . ?
C21 C17 H17 108.8 . . ?
O3 C18 H18A 109.1 . . ?
O3 C18 H18B 109.1 . . ?
O3 C18 C19 112.5(4) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.1 . . ?
C19 C18 H18B 109.1 . . ?
O4 C19 C18 107.9(4) . . ?
O4 C19 H19 109.2 . . ?
O4 C19 C20 111.1(4) . . ?
C18 C19 H19 109.2 . . ?
C18 C19 C20 110.3(4) . . ?
C20 C19 H19 109.2 . . ?
N2 C20 C19 111.3(4) . . ?
N2 C20 H20 108.9 . . ?
N2 C20 C21 109.7(4) . . ?
C19 C20 H20 108.9 . . ?
C21 C20 C19 109.2(4) . . ?
C21 C20 H20 108.9 . . ?
C17 C21 H21A 110.3 . . ?
C17 C21 H21B 110.3 . . ?
C20 C21 C17 106.9(4) . . ?
C20 C21 H21A 110.3 . . ?
C20 C21 H21B 110.3 . . ?
H21A C21 H21B 108.6 . . ?
N2 C22 C16 120.6(4) . . ?
N2 C22 C23 121.2(4) . . ?
C16 C22 C23 118.1(4) . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 120.9(4) . . ?
C24 C23 H23 119.5 . . ?
C14 C24 H24 118.9 . . ?
C23 C24 C14 122.1(5) . . ?
C23 C24 H24 118.9 . . ?

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 C5 C9 C8 -64.4(4) . . . . ?
O1 C6 C7 O2 -70.0(5) . . . . ?
O1 C6 C7 C8 51.4(5) . . . . ?
O2 C7 C8 N1 -173.3(3) . . . . ?
O2 C7 C8 C9 64.8(5) . . . . ?
O3 C17 C21 C20 -65.2(4) . . . . ?
O3 C18 C19 O4 -70.6(5) . . . . ?
O3 C18 C19 C20 50.9(5) . . . . ?
O4 C19 C20 N2 -173.4(4) . . . . ?
O4 C19 C20 C21 65.4(5) . . . . ?
N1 C8 C9 C5 -61.8(5) . . . . ?
N1 C10 C11 C12 178.0(4) . . . . ?
N2 C20 C21 C17 -60.5(5) . . . . ?
N2 C22 C23 C24 177.3(4) . . . . ?
C1 C2 C3 C4 -177.8(4) . . . . ?
C1 C2 C12 C11 179.5(4) . . . . ?
C2 C3 C4 C5 175.1(4) . . . . ?
C2 C3 C4 C10 -3.6(6) . . . . ?
C3 C2 C12 C11 -0.1(6) . . . . ?
C3 C4 C5 O1 -88.5(4) . . . . ?
C3 C4 C5 C9 150.0(4) . . . . ?
C3 C4 C10 N1 -176.5(4) . . . . ?
C3 C4 C10 C11 3.6(6) . . . . ?
C4 C5 C9 C8 58.5(5) . . . . ?
C4 C10 C11 C12 -2.1(6) . . . . ?
C5 O1 C6 C7 -55.8(5) . . . . ?
C5 C4 C10 N1 4.7(6) . . . . ?
C5 C4 C10 C11 -175.2(4) . . . . ?
C6 O1 C5 C4 -59.8(4) . . . . ?
C6 O1 C5 C9 63.1(4) . . . . ?
C6 C7 C8 N1 66.7(5) . . . . ?
C6 C7 C8 C9 -55.3(5) . . . . ?
C7 C8 C9 C5 61.5(5) . . . . ?
C8 N1 C10 C4 -8.6(6) . . . . ?
C8 N1 C10 C11 171.3(4) . . . . ?
C10 N1 C8 C7 -83.7(5) . . . . ?
C10 N1 C8 C9 38.0(5) . . . . ?
C10 C4 C5 O1 90.3(4) . . . . ?
C10 C4 C5 C9 -31.2(5) . . . . ?
C10 C11 C12 C2 0.3(7) . . . . ?
C12 C2 C3 C4 1.8(6) . . . . ?
C13 C14 C15 C16 -177.7(4) . . . . ?
C13 C14 C24 C23 178.6(4) . . . . ?
C14 C15 C16 C17 178.5(4) . . . . ?
C14 C15 C16 C22 -2.4(7) . . . . ?
C15 C14 C24 C23 -1.0(7) . . . . ?
C15 C16 C17 O3 -90.8(5) . . . . ?
C15 C16 C17 C21 149.3(4) . . . . ?
C15 C16 C22 N2 -176.4(4) . . . . ?
C15 C16 C22 C23 1.7(6) . . . . ?
C16 C17 C21 C20 57.6(5) . . . . ?
C16 C22 C23 C24 -0.8(6) . . . . ?
C17 O3 C18 C19 -56.7(5) . . . . ?
C17 C16 C22 N2 2.7(6) . . . . ?
C17 C16 C22 C23 -179.1(4) . . . . ?
C18 O3 C17 C16 -58.3(5) . . . . ?
C18 O3 C17 C21 63.5(4) . . . . ?
C18 C19 C20 N2 67.0(4) . . . . ?
C18 C19 C20 C21 -54.2(5) . . . . ?
C19 C20 C21 C17 61.7(5) . . . . ?
C20 N2 C22 C16 -6.1(6) . . . . ?
C20 N2 C22 C23 175.8(4) . . . . ?
C22 N2 C20 C19 -84.9(5) . . . . ?
C22 N2 C20 C21 36.0(5) . . . . ?
C22 C16 C17 O3 90.1(5) . . . . ?
C22 C16 C17 C21 -29.8(6) . . . . ?
C22 C23 C24 C14 0.5(7) . . . . ?
C24 C14 C15 C16 2.0(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
