# 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 
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data_230909_ngh_c069_3a_zlj_0m
_database_code_depnum_ccdc_archive 'CCDC 2296214'
loop_
_audit_author_name
_audit_author_address
q
;Guizhou University
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6651(6)
_cell_length_b                   10.0573(7)
_cell_length_c                   18.1252(12)
_cell_angle_alpha                83.474(2)
_cell_angle_beta                 89.157(2)
_cell_angle_gamma                70.718(2)
_cell_volume                     1651.76(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9622
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.684
_cell_measurement_theta_min      4.079
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.414
_exptl_absorpt_correction_T_max  0.7518
_exptl_absorpt_correction_T_min  0.6473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1695 before and 0.0955 after correction.
The Ratio of minimum to maximum transmission is 0.8610.
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    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32984
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.901
_diffrn_reflns_theta_min         2.135
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24957869999999996
_diffrn_source_voltage           69.91
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5563
_reflns_number_total             7473
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.719
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     447
_refine_ls_number_reflns         7473
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0910
_refine_ls_R_factor_gt           0.0723
_refine_ls_restrained_S_all      1.085
_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)+(0.1015P)²+0.9051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1966
_refine_ls_wR_factor_ref         0.2090
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C33-C32 \\sim C33-C32A
 with sigma of 0.02
 C31-C32 \\sim C31-C32A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C31 \\sim C32 \\sim C32A \\sim C33: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
4. Others
 Sof(H33C)=Sof(H33D)=Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=1-FVAR(1)
 Sof(H33A)=Sof(H33B)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C30(H30), C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C33(H33A,H33B), C33(H33C,H33D), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,
 H12B), C31(H31A,H31B), C31(H31C,H31D), C32(H32A,H32B), C32A(H32C,H32D)
5.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C19(H19), C37(H37), C17(H17), C16(H16), C22(H22), C38(H38),
 C25(H25), C41(H41), C2(H2), C40(H40), C1(H1), C23(H23), C4(H4), C24(H24),
 C3(H3)
5.d Idealised Me refined as rotating group:
 C34(H34A,H34B,H34C), C13(H13A,H13B,H13C), C21(H21A,H21B,H21C), C42(H42A,H42B,
 H42C)
;
_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
O2 O 0.58540(18) -0.01237(19) 0.83616(10) 0.0450(4) Uani 1 1 d . . . . .
O3 O 0.58410(18) 0.71274(18) 0.62487(11) 0.0482(5) Uani 1 1 d . . . . .
O1 O 1.0122(2) 0.3502(2) 0.78762(9) 0.0480(5) Uani 1 1 d . . . . .
O4 O 1.1136(2) 0.94242(19) 0.64088(11) 0.0507(5) Uani 1 1 d . . . . .
N1 N 1.00864(19) 0.59178(19) 0.88958(10) 0.0332(4) Uani 1 1 d . . . . .
N2 N 0.5414(2) 0.4296(2) 0.68231(10) 0.0370(4) Uani 1 1 d . . . . .
C27 C 0.5026(2) 0.3041(2) 0.59398(12) 0.0347(5) Uani 1 1 d . . . . .
C29 C 0.6483(2) 0.4211(2) 0.62897(12) 0.0329(5) Uani 1 1 d . . . . .
C5 C 1.1065(2) 0.6651(2) 0.88878(12) 0.0334(5) Uani 1 1 d . . . . .
C15 C 0.8715(2) 0.2173(2) 0.84448(12) 0.0323(5) Uani 1 1 d . . . . .
C14 C 0.9678(2) 0.3048(2) 0.84550(12) 0.0333(5) Uani 1 1 d . . . . .
C20 C 0.8021(2) 0.1776(2) 0.90822(12) 0.0351(5) Uani 1 1 d . . . . .
H20 H 0.819838 0.204145 0.954897 0.042 Uiso 1 1 calc R U . . .
C26 C 0.4514(2) 0.3587(2) 0.66118(13) 0.0358(5) Uani 1 1 d . . . . .
C35 C 0.7142(2) 0.6438(2) 0.63138(12) 0.0347(5) Uani 1 1 d . . . . .
C18 C 0.6799(2) 0.0626(2) 0.83520(13) 0.0357(5) Uani 1 1 d . . . . .
C36 C 0.8247(2) 0.7163(2) 0.63596(12) 0.0339(5) Uani 1 1 d . . . . .
C28 C 0.6275(2) 0.3454(2) 0.57451(12) 0.0336(5) Uani 1 1 d . . . . .
C19 C 0.7092(2) 0.1010(2) 0.90333(13) 0.0377(5) Uani 1 1 d . . . . .
H19 H 0.664443 0.073713 0.946802 0.045 Uiso 1 1 calc R U . . .
C37 C 0.9632(2) 0.6499(2) 0.66879(12) 0.0353(5) Uani 1 1 d . . . . .
H37 H 0.990462 0.553084 0.688907 0.042 Uiso 1 1 calc R U . . .
C17 C 0.7480(3) 0.0993(2) 0.77164(13) 0.0374(5) Uani 1 1 d . . . . .
H17 H 0.729295 0.073014 0.725057 0.045 Uiso 1 1 calc R U . . .
C8 C 1.0850(3) 0.4498(2) 0.91100(12) 0.0351(5) Uani 1 1 d . . . . .
C30 C 0.7688(2) 0.4829(2) 0.63215(13) 0.0360(5) Uani 1 1 d . . . . .
H30 H 0.829914 0.439140 0.678247 0.043 Uiso 1 1 calc R U . . .
C39 C 1.0235(3) 0.8629(2) 0.64168(13) 0.0386(5) Uani 1 1 d . . . . .
C16 C 0.8432(2) 0.1745(2) 0.77728(12) 0.0355(5) Uani 1 1 d . . . . .
H16 H 0.890982 0.197850 0.734017 0.043 Uiso 1 1 calc R U . . .
C22 C 0.4295(3) 0.2264(3) 0.56041(14) 0.0416(5) Uani 1 1 d . . . . .
H22 H 0.463507 0.187279 0.515576 0.050 Uiso 1 1 calc R U . . .
C38 C 1.0621(3) 0.7224(3) 0.67268(13) 0.0379(5) Uani 1 1 d . . . . .
H38 H 1.155465 0.676295 0.696344 0.045 Uiso 1 1 calc R U . . .
C25 C 0.3281(3) 0.3385(3) 0.69546(15) 0.0437(6) Uani 1 1 d . . . . .
H25 H 0.294734 0.374874 0.741003 0.052 Uiso 1 1 calc R U . . .
C7 C 1.2286(3) 0.4325(3) 0.92396(13) 0.0405(5) Uani 1 1 d . . . . .
C6 C 1.2446(3) 0.5685(3) 0.91106(13) 0.0381(5) Uani 1 1 d . . . . .
C33 C 0.7259(3) 0.3149(3) 0.50945(13) 0.0405(5) Uani 1 1 d D U . . .
H33A H 0.684530 0.387195 0.466599 0.049 Uiso 0.733(7) 1 calc R U P A 1
H33B H 0.734574 0.220670 0.494827 0.049 Uiso 0.733(7) 1 calc R U P A 1
H33C H 0.792625 0.215478 0.516304 0.049 Uiso 0.267(7) 1 calc R U P A 2
H33D H 0.666957 0.329660 0.463171 0.049 Uiso 0.267(7) 1 calc R U P A 2
C9 C 1.0194(3) 0.3347(2) 0.91982(13) 0.0377(5) Uani 1 1 d . . . . .
H9 H 0.933400 0.362427 0.952986 0.045 Uiso 1 1 calc R U . . .
C10 C 1.1358(3) 0.1959(2) 0.95720(13) 0.0407(5) Uani 1 1 d . . . . .
H10A H 1.140816 0.200592 1.011320 0.049 Uiso 1 1 calc R U . . .
H10B H 1.105382 0.113495 0.949655 0.049 Uiso 1 1 calc R U . . .
C34 C 0.5310(3) 0.4913(3) 0.75139(13) 0.0448(6) Uani 1 1 d . . . . .
H34A H 0.616552 0.521022 0.757800 0.067 Uiso 1 1 calc R U . . .
H34B H 0.527901 0.420878 0.792874 0.067 Uiso 1 1 calc R U . . .
H34C H 0.441465 0.573851 0.750280 0.067 Uiso 1 1 calc R U . . .
C41 C 0.7875(3) 0.8592(3) 0.60635(14) 0.0423(6) Uani 1 1 d . . . . .
H41 H 0.692848 0.907115 0.584463 0.051 Uiso 1 1 calc R U . . .
C2 C 1.3364(3) 0.7651(3) 0.89717(13) 0.0446(6) Uani 1 1 d . . . . .
H2 H 1.414770 0.801711 0.900201 0.054 Uiso 1 1 calc R U . . .
C40 C 0.8860(3) 0.9303(3) 0.60864(15) 0.0458(6) Uani 1 1 d . . . . .
H40 H 0.859949 1.026441 0.587465 0.055 Uiso 1 1 calc R U . . .
C1 C 1.3637(3) 0.6233(3) 0.91599(14) 0.0449(6) Uani 1 1 d . . . . .
H1 H 1.459031 0.562338 0.931935 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8560(3) 0.6487(3) 0.86469(14) 0.0449(6) Uani 1 1 d . . . . .
H13A H 0.818501 0.750744 0.868711 0.067 Uiso 1 1 calc R U . . .
H13B H 0.798384 0.601249 0.895729 0.067 Uiso 1 1 calc R U . . .
H13C H 0.848308 0.632543 0.812829 0.067 Uiso 1 1 calc R U . . .
C23 C 0.3060(3) 0.2078(3) 0.59422(16) 0.0487(6) Uani 1 1 d . . . . .
H23 H 0.254397 0.156490 0.571846 0.058 Uiso 1 1 calc R U . . .
C4 C 1.0821(3) 0.8106(3) 0.86927(14) 0.0450(6) Uani 1 1 d . . . . .
H4 H 0.987669 0.873943 0.853473 0.054 Uiso 1 1 calc R U . . .
C24 C 0.2568(3) 0.2636(3) 0.66060(16) 0.0492(6) Uani 1 1 d . . . . .
H24 H 0.171963 0.249640 0.682393 0.059 Uiso 1 1 calc R U . . .
C3 C 1.1991(3) 0.8580(3) 0.87383(15) 0.0497(6) Uani 1 1 d . . . . .
H3 H 1.185845 0.955644 0.860815 0.060 Uiso 1 1 calc R U . . .
C11 C 1.2869(3) 0.1754(3) 0.92486(15) 0.0474(6) Uani 1 1 d . . . . .
H11A H 1.355362 0.081570 0.945166 0.057 Uiso 1 1 calc R U . . .
H11B H 1.280533 0.177425 0.870259 0.057 Uiso 1 1 calc R U . . .
C12 C 1.3455(3) 0.2904(3) 0.94324(17) 0.0504(7) Uani 1 1 d . . . . .
H12A H 1.372148 0.276572 0.996776 0.060 Uiso 1 1 calc R U . . .
H12B H 1.434511 0.285969 0.914467 0.060 Uiso 1 1 calc R U . . .
C21 C 0.5493(3) -0.0490(3) 0.76672(16) 0.0532(7) Uani 1 1 d . . . . .
H21A H 0.505795 0.037555 0.732612 0.080 Uiso 1 1 calc R U . . .
H21B H 0.478884 -0.100210 0.774693 0.080 Uiso 1 1 calc R U . . .
H21C H 0.638364 -0.109468 0.745281 0.080 Uiso 1 1 calc R U . . .
C42 C 1.2596(3) 0.8731(3) 0.66887(16) 0.0512(7) Uani 1 1 d . . . . .
H42A H 1.307366 0.792322 0.641288 0.077 Uiso 1 1 calc R U . . .
H42B H 1.257585 0.839281 0.721636 0.077 Uiso 1 1 calc R U . . .
H42C H 1.314466 0.939841 0.662978 0.077 Uiso 1 1 calc R U . . .
C31 C 0.8674(3) 0.4492(4) 0.56305(19) 0.0633(9) Uani 1 1 d D U . . .
H31A H 0.828421 0.528749 0.523246 0.076 Uiso 0.733(7) 1 calc R U P A 1
H31B H 0.966998 0.446819 0.576772 0.076 Uiso 0.733(7) 1 calc R U P A 1
H31C H 0.895766 0.533502 0.546143 0.076 Uiso 0.267(7) 1 calc R U P A 2
H31D H 0.958380 0.370806 0.579431 0.076 Uiso 0.267(7) 1 calc R U P A 2
C32 C 0.8807(3) 0.3179(4) 0.53239(18) 0.0386(10) Uani 0.733(7) 1 d D U P A 1
H32A H 0.927963 0.236118 0.569825 0.046 Uiso 0.733(7) 1 calc R U P A 1
H32B H 0.943597 0.309666 0.488369 0.046 Uiso 0.733(7) 1 calc R U P A 1
C32A C 0.8113(9) 0.4137(9) 0.5051(4) 0.034(2) Uani 0.267(7) 1 d D U P A 2
H32C H 0.894489 0.374818 0.472422 0.041 Uiso 0.267(7) 1 calc R U P A 2
H32D H 0.747783 0.503722 0.477827 0.041 Uiso 0.267(7) 1 calc R U P A 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
O2 C18 1.362(3) . ?
O2 C21 1.430(3) . ?
O3 C35 1.219(3) . ?
O1 C14 1.225(3) . ?
O4 C39 1.362(3) . ?
O4 C42 1.423(3) . ?
N1 C5 1.377(3) . ?
N1 C8 1.386(3) . ?
N1 C13 1.452(3) . ?
N2 C29 1.393(3) . ?
N2 C26 1.376(3) . ?
N2 C34 1.447(3) . ?
C27 C26 1.409(3) . ?
C27 C28 1.429(3) . ?
C27 C22 1.402(3) . ?
C29 C28 1.368(3) . ?
C29 C30 1.495(3) . ?
C5 C6 1.399(3) . ?
C5 C4 1.407(3) . ?
C15 C14 1.479(3) . ?
C15 C20 1.412(3) . ?
C15 C16 1.397(3) . ?
C14 C9 1.537(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.372(3) . ?
C26 C25 1.399(3) . ?
C35 C36 1.488(3) . ?
C35 C30 1.526(3) . ?
C18 C19 1.394(3) . ?
C18 C17 1.392(3) . ?
C36 C37 1.390(3) . ?
C36 C41 1.404(3) . ?
C28 C33 1.498(3) . ?
C19 H19 0.9500 . ?
C37 H37 0.9500 . ?
C37 C38 1.388(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.381(3) . ?
C8 C7 1.361(3) . ?
C8 C9 1.486(3) . ?
C30 H30 1.0000 . ?
C30 C31 1.562(3) . ?
C39 C38 1.389(3) . ?
C39 C40 1.385(3) . ?
C16 H16 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.391(4) . ?
C38 H38 0.9500 . ?
C25 H25 0.9500 . ?
C25 C24 1.380(4) . ?
C7 C6 1.419(4) . ?
C7 C12 1.508(3) . ?
C6 C1 1.439(3) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 H33C 0.9900 . ?
C33 H33D 0.9900 . ?
C33 C32 1.570(4) . ?
C33 C32A 1.482(8) . ?
C9 H9 1.0000 . ?
C9 C10 1.563(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.524(3) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C41 H41 0.9500 . ?
C41 C40 1.371(4) . ?
C2 H2 0.9500 . ?
C2 C1 1.365(4) . ?
C2 C3 1.386(4) . ?
C40 H40 0.9500 . ?
C1 H1 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C24 1.396(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.371(4) . ?
C24 H24 0.9500 . ?
C3 H3 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.515(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 H31C 0.9900 . ?
C31 H31D 0.9900 . ?
C31 C32 1.456(4) . ?
C31 C32A 1.325(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?

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
C18 O2 C21 117.43(19) . . ?
C39 O4 C42 117.31(19) . . ?
C5 N1 C8 107.91(18) . . ?
C5 N1 C13 126.5(2) . . ?
C8 N1 C13 125.2(2) . . ?
C29 N2 C34 127.0(2) . . ?
C26 N2 C29 108.17(19) . . ?
C26 N2 C34 124.66(19) . . ?
C26 C27 C28 107.0(2) . . ?
C22 C27 C26 119.6(2) . . ?
C22 C27 C28 133.4(2) . . ?
N2 C29 C30 124.8(2) . . ?
C28 C29 N2 109.6(2) . . ?
C28 C29 C30 125.56(19) . . ?
N1 C5 C6 108.21(19) . . ?
N1 C5 C4 129.2(2) . . ?
C6 C5 C4 122.6(2) . . ?
C20 C15 C14 123.1(2) . . ?
C16 C15 C14 119.18(19) . . ?
C16 C15 C20 117.6(2) . . ?
O1 C14 C15 120.8(2) . . ?
O1 C14 C9 118.9(2) . . ?
C15 C14 C9 120.22(18) . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
N2 C26 C27 108.18(19) . . ?
N2 C26 C25 130.1(2) . . ?
C25 C26 C27 121.7(2) . . ?
O3 C35 C36 120.2(2) . . ?
O3 C35 C30 121.6(2) . . ?
C36 C35 C30 118.20(18) . . ?
O2 C18 C19 116.1(2) . . ?
O2 C18 C17 124.0(2) . . ?
C17 C18 C19 119.9(2) . . ?
C37 C36 C35 123.2(2) . . ?
C37 C36 C41 118.2(2) . . ?
C41 C36 C35 118.6(2) . . ?
C27 C28 C33 130.0(2) . . ?
C29 C28 C27 107.07(19) . . ?
C29 C28 C33 122.9(2) . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C36 C37 H37 119.4 . . ?
C38 C37 C36 121.2(2) . . ?
C38 C37 H37 119.4 . . ?
C18 C17 H17 120.5 . . ?
C16 C17 C18 119.0(2) . . ?
C16 C17 H17 120.5 . . ?
N1 C8 C9 125.1(2) . . ?
C7 C8 N1 109.5(2) . . ?
C7 C8 C9 125.3(2) . . ?
C29 C30 C35 113.59(18) . . ?
C29 C30 H30 109.0 . . ?
C29 C30 C31 109.5(2) . . ?
C35 C30 H30 109.0 . . ?
C35 C30 C31 106.7(2) . . ?
C31 C30 H30 109.0 . . ?
O4 C39 C38 124.1(2) . . ?
O4 C39 C40 115.9(2) . . ?
C40 C39 C38 120.0(2) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.2(2) . . ?
C17 C16 H16 118.9 . . ?
C27 C22 H22 120.7 . . ?
C23 C22 C27 118.5(2) . . ?
C23 C22 H22 120.7 . . ?
C37 C38 C39 119.4(2) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C26 C25 H25 121.3 . . ?
C24 C25 C26 117.5(2) . . ?
C24 C25 H25 121.3 . . ?
C8 C7 C6 107.4(2) . . ?
C8 C7 C12 123.9(2) . . ?
C6 C7 C12 128.6(2) . . ?
C5 C6 C7 107.0(2) . . ?
C5 C6 C1 117.7(2) . . ?
C7 C6 C1 135.4(2) . . ?
C28 C33 H33A 110.0 . . ?
C28 C33 H33B 110.0 . . ?
C28 C33 H33C 110.3 . . ?
C28 C33 H33D 110.3 . . ?
C28 C33 C32 108.4(2) . . ?
H33A C33 H33B 108.4 . . ?
H33C C33 H33D 108.5 . . ?
C32 C33 H33A 110.0 . . ?
C32 C33 H33B 110.0 . . ?
C32A C33 C28 107.2(3) . . ?
C32A C33 H33C 110.3 . . ?
C32A C33 H33D 110.3 . . ?
C14 C9 H9 108.8 . . ?
C14 C9 C10 108.76(18) . . ?
C8 C9 C14 112.79(18) . . ?
C8 C9 H9 108.8 . . ?
C8 C9 C10 108.9(2) . . ?
C10 C9 H9 108.8 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 C9 111.32(19) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N2 C34 H34A 109.5 . . ?
N2 C34 H34B 109.5 . . ?
N2 C34 H34C 109.5 . . ?
H34A C34 H34B 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C41 H41 119.6 . . ?
C40 C41 C36 120.8(2) . . ?
C40 C41 H41 119.6 . . ?
C1 C2 H2 118.6 . . ?
C1 C2 C3 122.8(2) . . ?
C3 C2 H2 118.6 . . ?
C39 C40 H40 119.8 . . ?
C41 C40 C39 120.4(2) . . ?
C41 C40 H40 119.8 . . ?
C6 C1 H1 120.8 . . ?
C2 C1 C6 118.3(2) . . ?
C2 C1 H1 120.8 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 C23 H23 119.6 . . ?
C22 C23 C24 120.8(3) . . ?
C24 C23 H23 119.6 . . ?
C5 C4 H4 121.1 . . ?
C3 C4 C5 117.8(2) . . ?
C3 C4 H4 121.1 . . ?
C25 C24 C23 121.8(2) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3 119.6 . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 C10 111.1(2) . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C7 C12 C11 108.7(2) . . ?
C7 C12 H12A 110.0 . . ?
C7 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.3 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C42 H42A 109.5 . . ?
O4 C42 H42B 109.5 . . ?
O4 C42 H42C 109.5 . . ?
H42A C42 H42B 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C30 C31 H31A 108.0 . . ?
C30 C31 H31B 108.0 . . ?
C30 C31 H31C 107.9 . . ?
C30 C31 H31D 107.9 . . ?
H31A C31 H31B 107.3 . . ?
H31C C31 H31D 107.2 . . ?
C32 C31 C30 117.1(3) . . ?
C32 C31 H31A 108.0 . . ?
C32 C31 H31B 108.0 . . ?
C32A C31 C30 117.5(4) . . ?
C32A C31 H31C 107.9 . . ?
C32A C31 H31D 107.9 . . ?
C33 C32 H32A 109.5 . . ?
C33 C32 H32B 109.5 . . ?
C31 C32 C33 110.6(3) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 108.1 . . ?
C33 C32A H32C 106.1 . . ?
C33 C32A H32D 106.1 . . ?
C31 C32A C33 124.8(6) . . ?
C31 C32A H32C 106.1 . . ?
C31 C32A H32D 106.1 . . ?
H32C C32A H32D 106.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C18 C19 C20 -179.49(19) . . . . ?
O2 C18 C17 C16 -179.4(2) . . . . ?
O3 C35 C36 C37 156.4(2) . . . . ?
O3 C35 C36 C41 -23.1(3) . . . . ?
O3 C35 C30 C29 -3.5(3) . . . . ?
O3 C35 C30 C31 117.3(2) . . . . ?
O1 C14 C9 C8 16.1(3) . . . . ?
O1 C14 C9 C10 -104.9(2) . . . . ?
O4 C39 C38 C37 -178.3(2) . . . . ?
O4 C39 C40 C41 179.8(2) . . . . ?
N1 C5 C6 C7 1.3(2) . . . . ?
N1 C5 C6 C1 -178.52(19) . . . . ?
N1 C5 C4 C3 179.4(2) . . . . ?
N1 C8 C7 C6 0.5(3) . . . . ?
N1 C8 C7 C12 -175.7(2) . . . . ?
N1 C8 C9 C14 68.6(3) . . . . ?
N1 C8 C9 C10 -170.56(19) . . . . ?
N2 C29 C28 C27 0.0(2) . . . . ?
N2 C29 C28 C33 -179.0(2) . . . . ?
N2 C29 C30 C35 -61.7(3) . . . . ?
N2 C29 C30 C31 179.1(2) . . . . ?
N2 C26 C25 C24 179.0(2) . . . . ?
C27 C26 C25 C24 -0.6(3) . . . . ?
C27 C28 C33 C32 -153.1(2) . . . . ?
C27 C28 C33 C32A 164.8(4) . . . . ?
C27 C22 C23 C24 -0.8(4) . . . . ?
C29 N2 C26 C27 0.4(2) . . . . ?
C29 N2 C26 C25 -179.3(2) . . . . ?
C29 C28 C33 C32 25.6(3) . . . . ?
C29 C28 C33 C32A -16.5(5) . . . . ?
C29 C30 C31 C32 -30.6(4) . . . . ?
C29 C30 C31 C32A 19.2(6) . . . . ?
C5 N1 C8 C7 0.3(2) . . . . ?
C5 N1 C8 C9 179.2(2) . . . . ?
C5 C6 C1 C2 -1.4(3) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C15 C14 C9 C8 -166.56(19) . . . . ?
C15 C14 C9 C10 72.5(2) . . . . ?
C15 C20 C19 C18 -0.9(3) . . . . ?
C14 C15 C20 C19 177.4(2) . . . . ?
C14 C15 C16 C17 -176.4(2) . . . . ?
C14 C9 C10 C11 81.3(2) . . . . ?
C20 C15 C14 O1 -171.6(2) . . . . ?
C20 C15 C14 C9 11.1(3) . . . . ?
C20 C15 C16 C17 1.8(3) . . . . ?
C26 N2 C29 C28 -0.2(2) . . . . ?
C26 N2 C29 C30 -179.0(2) . . . . ?
C26 C27 C28 C29 0.2(2) . . . . ?
C26 C27 C28 C33 179.1(2) . . . . ?
C26 C27 C22 C23 1.1(3) . . . . ?
C26 C25 C24 C23 0.9(4) . . . . ?
C35 C36 C37 C38 -179.1(2) . . . . ?
C35 C36 C41 C40 -179.4(2) . . . . ?
C35 C30 C31 C32 -154.0(3) . . . . ?
C35 C30 C31 C32A -104.1(5) . . . . ?
C18 C17 C16 C15 -1.2(3) . . . . ?
C36 C35 C30 C29 178.74(18) . . . . ?
C36 C35 C30 C31 -60.4(3) . . . . ?
C36 C37 C38 C39 -1.5(3) . . . . ?
C36 C41 C40 C39 -1.3(4) . . . . ?
C28 C27 C26 N2 -0.4(2) . . . . ?
C28 C27 C26 C25 179.3(2) . . . . ?
C28 C27 C22 C23 -178.5(2) . . . . ?
C28 C29 C30 C35 119.8(2) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C28 C33 C32 C31 -52.4(3) . . . . ?
C28 C33 C32A C31 40.1(9) . . . . ?
C19 C18 C17 C16 -0.5(3) . . . . ?
C37 C36 C41 C40 1.1(4) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C8 N1 C5 C6 -1.0(2) . . . . ?
C8 N1 C5 C4 178.5(2) . . . . ?
C8 C7 C6 C5 -1.1(3) . . . . ?
C8 C7 C6 C1 178.6(3) . . . . ?
C8 C7 C12 C11 15.4(3) . . . . ?
C8 C9 C10 C11 -42.0(3) . . . . ?
C30 C29 C28 C27 178.7(2) . . . . ?
C30 C29 C28 C33 -0.3(3) . . . . ?
C30 C35 C36 C37 -25.9(3) . . . . ?
C30 C35 C36 C41 154.7(2) . . . . ?
C30 C31 C32 C33 57.8(4) . . . . ?
C30 C31 C32A C33 -43.4(9) . . . . ?
C16 C15 C14 O1 6.5(3) . . . . ?
C16 C15 C14 C9 -170.84(19) . . . . ?
C16 C15 C20 C19 -0.7(3) . . . . ?
C22 C27 C26 N2 179.9(2) . . . . ?
C22 C27 C26 C25 -0.4(3) . . . . ?
C22 C27 C28 C29 179.9(2) . . . . ?
C22 C27 C28 C33 -1.2(4) . . . . ?
C22 C23 C24 C25 -0.2(4) . . . . ?
C38 C39 C40 C41 0.0(4) . . . . ?
C7 C8 C9 C14 -112.7(2) . . . . ?
C7 C8 C9 C10 8.2(3) . . . . ?
C7 C6 C1 C2 178.8(3) . . . . ?
C6 C5 C4 C3 -1.1(3) . . . . ?
C6 C7 C12 C11 -160.0(2) . . . . ?
C9 C8 C7 C6 -178.4(2) . . . . ?
C9 C8 C7 C12 5.4(4) . . . . ?
C9 C10 C11 C12 65.8(3) . . . . ?
C10 C11 C12 C7 -49.3(3) . . . . ?
C34 N2 C29 C28 175.1(2) . . . . ?
C34 N2 C29 C30 -3.6(4) . . . . ?
C34 N2 C26 C27 -175.1(2) . . . . ?
C34 N2 C26 C25 5.2(4) . . . . ?
C41 C36 C37 C38 0.3(3) . . . . ?
C40 C39 C38 C37 1.4(4) . . . . ?
C1 C2 C3 C4 0.7(4) . . . . ?
C13 N1 C5 C6 -174.7(2) . . . . ?
C13 N1 C5 C4 4.8(4) . . . . ?
C13 N1 C8 C7 174.1(2) . . . . ?
C13 N1 C8 C9 -7.0(3) . . . . ?
C4 C5 C6 C7 -178.2(2) . . . . ?
C4 C5 C6 C1 1.9(3) . . . . ?
C3 C2 C1 C6 0.2(4) . . . . ?
C12 C7 C6 C5 174.9(2) . . . . ?
C12 C7 C6 C1 -5.3(5) . . . . ?
C21 O2 C18 C19 177.9(2) . . . . ?
C21 O2 C18 C17 -3.2(3) . . . . ?
C42 O4 C39 C38 4.7(4) . . . . ?
C42 O4 C39 C40 -175.0(2) . . . . ?

_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_230909_ngh_c069_3b_zlj_0m
_database_code_depnum_ccdc_archive 'CCDC 2296215'
loop_
_audit_author_name
_audit_author_address
Q
;Guizhou University
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H21 N O2'
_chemical_formula_sum            'C21 H21 N O2'
_chemical_formula_weight         319.39
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   8.746(5)
_cell_length_b                   14.913(9)
_cell_length_c                   12.807(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.41(2)
_cell_angle_gamma                90
_cell_volume                     1660.0(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      56.676
_cell_measurement_theta_min      3.973
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.412
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1329 before and 0.0769 after correction.
The Ratio of minimum to maximum transmission is 0.7533.
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    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.1316
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11402
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         53.902
_diffrn_reflns_theta_min         3.973
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1895
_reflns_number_total             3003
_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 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.061
_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)+(0.0565P)²+0.1165P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1548
_refine_ls_wR_factor_ref         0.1759
_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:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C16(H16), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7558(2) 0.78710(11) 0.45199(14) 0.0570(6) Uani 1 1 d . . . . .
O2 O 1.2887(2) 0.49827(11) 0.49733(14) 0.0571(6) Uani 1 1 d . . . . .
N1 N 0.4873(3) 0.96435(13) 0.64271(16) 0.0438(6) Uani 1 1 d . . . . .
C1 C 0.8847(3) 0.99970(16) 0.6146(2) 0.0477(7) Uani 1 1 d . . . . .
H1 H 0.973539 0.963189 0.613722 0.057 Uiso 1 1 calc R U . . .
C2 C 0.8949(4) 1.09258(17) 0.60426(19) 0.0513(8) Uani 1 1 d . . . . .
H2 H 0.991543 1.119506 0.596919 0.062 Uiso 1 1 calc R U . . .
C3 C 0.7631(4) 1.14670(17) 0.6046(2) 0.0523(8) Uani 1 1 d . . . . .
H3 H 0.772251 1.209702 0.596244 0.063 Uiso 1 1 calc R U . . .
C4 C 0.6213(4) 1.11062(16) 0.61674(19) 0.0469(7) Uani 1 1 d . . . . .
H4 H 0.532706 1.147463 0.616920 0.056 Uiso 1 1 calc R U . . .
C5 C 0.6127(3) 1.01740(15) 0.62883(19) 0.0421(7) Uani 1 1 d . . . . .
C6 C 0.7419(3) 0.96108(15) 0.62633(18) 0.0428(7) Uani 1 1 d . . . . .
C7 C 0.6891(3) 0.87024(14) 0.63808(18) 0.0422(7) Uani 1 1 d . . . . .
C8 C 0.5358(3) 0.87527(15) 0.64814(19) 0.0434(7) Uani 1 1 d . . . . .
C9 C 0.4311(4) 0.79774(15) 0.6628(2) 0.0510(7) Uani 1 1 d . . . . .
H9A H 0.332484 0.805277 0.617536 0.061 Uiso 1 1 calc R U . . .
H9B H 0.409037 0.794554 0.736835 0.061 Uiso 1 1 calc R U . . .
C10 C 0.5114(4) 0.71201(16) 0.6329(2) 0.0525(8) Uani 1 1 d . . . . .
H10A H 0.455228 0.659507 0.656641 0.063 Uiso 1 1 calc R U . . .
H10B H 0.507695 0.708736 0.555484 0.063 Uiso 1 1 calc R U . . .
C11 C 0.6788(4) 0.70746(15) 0.6813(2) 0.0526(8) Uani 1 1 d . . . . .
H11A H 0.722939 0.648845 0.664124 0.063 Uiso 1 1 calc R U . . .
H11B H 0.682925 0.711729 0.758680 0.063 Uiso 1 1 calc R U . . .
C12 C 0.7775(3) 0.78409(15) 0.64049(19) 0.0446(7) Uani 1 1 d . . . . .
H12 H 0.872874 0.791115 0.690687 0.053 Uiso 1 1 calc R U . . .
C13 C 0.3319(3) 0.99564(17) 0.6492(2) 0.0538(8) Uani 1 1 d . . . . .
H13A H 0.311834 0.997148 0.722986 0.081 Uiso 1 1 calc R U . . .
H13B H 0.258774 0.954908 0.609860 0.081 Uiso 1 1 calc R U . . .
H13C H 0.319970 1.056037 0.619291 0.081 Uiso 1 1 calc R U . . .
C14 C 0.8249(3) 0.75744(15) 0.53299(19) 0.0425(7) Uani 1 1 d . . . . .
C15 C 0.9521(3) 0.69125(15) 0.52939(18) 0.0421(7) Uani 1 1 d . . . . .
C16 C 1.0344(3) 0.65415(16) 0.61796(19) 0.0467(7) Uani 1 1 d . . . . .
H16 H 1.012215 0.673246 0.685422 0.056 Uiso 1 1 calc R U . . .
C17 C 1.1480(3) 0.59007(16) 0.61113(19) 0.0475(7) Uani 1 1 d . . . . .
H17 H 1.202763 0.565976 0.673042 0.057 Uiso 1 1 calc R U . . .
C18 C 1.1805(3) 0.56172(15) 0.5134(2) 0.0445(7) Uani 1 1 d . . . . .
C19 C 1.1007(3) 0.59830(17) 0.4231(2) 0.0511(7) Uani 1 1 d . . . . .
H19 H 1.124212 0.579632 0.355774 0.061 Uiso 1 1 calc R U . . .
C20 C 0.9881(3) 0.66128(16) 0.43121(19) 0.0481(7) Uani 1 1 d . . . . .
H20 H 0.933380 0.685038 0.369075 0.058 Uiso 1 1 calc R U . . .
C21 C 1.3692(4) 0.45597(18) 0.5877(2) 0.0575(8) Uani 1 1 d . . . . .
H21A H 1.437725 0.409587 0.565102 0.086 Uiso 1 1 calc R U . . .
H21B H 1.294933 0.428519 0.629965 0.086 Uiso 1 1 calc R U . . .
H21C H 1.430078 0.500869 0.630012 0.086 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 C14 1.223(3) . ?
O2 C18 1.369(3) . ?
O2 C21 1.433(3) . ?
N1 C5 1.380(3) . ?
N1 C8 1.394(3) . ?
N1 C13 1.448(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(4) . ?
C1 C6 1.398(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.407(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.402(3) . ?
C5 C6 1.411(4) . ?
C6 C7 1.444(3) . ?
C7 C8 1.363(4) . ?
C7 C12 1.498(4) . ?
C8 C9 1.500(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.526(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.557(4) . ?
C12 H12 1.0000 . ?
C12 C14 1.534(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.492(4) . ?
C15 C16 1.389(4) . ?
C15 C20 1.403(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.381(4) . ?
C18 C19 1.393(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.373(4) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C18 O2 C21 117.9(2) . . ?
C5 N1 C8 108.1(2) . . ?
C5 N1 C13 126.0(2) . . ?
C8 N1 C13 125.9(2) . . ?
C2 C1 H1 120.4 . . ?
C2 C1 C6 119.1(3) . . ?
C6 C1 H1 120.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.5(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(2) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.4(3) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C4 129.5(3) . . ?
N1 C5 C6 108.2(2) . . ?
C4 C5 C6 122.3(3) . . ?
C1 C6 C5 119.0(2) . . ?
C1 C6 C7 134.2(3) . . ?
C5 C6 C7 106.8(2) . . ?
C6 C7 C12 129.5(3) . . ?
C8 C7 C6 106.7(2) . . ?
C8 C7 C12 123.8(2) . . ?
N1 C8 C9 123.6(3) . . ?
C7 C8 N1 110.2(2) . . ?
C7 C8 C9 126.2(2) . . ?
C8 C9 H9A 110.1 . . ?
C8 C9 H9B 110.1 . . ?
C8 C9 C10 108.0(2) . . ?
H9A C9 H9B 108.4 . . ?
C10 C9 H9A 110.1 . . ?
C10 C9 H9B 110.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 112.5(2) . . ?
C11 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C10 C11 C12 112.0(2) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C7 C12 C11 109.4(2) . . ?
C7 C12 H12 108.4 . . ?
C7 C12 C14 113.2(2) . . ?
C11 C12 H12 108.4 . . ?
C14 C12 C11 109.04(19) . . ?
C14 C12 H12 108.4 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C14 C12 120.7(2) . . ?
O1 C14 C15 120.8(2) . . ?
C15 C14 C12 118.4(2) . . ?
C16 C15 C14 124.0(2) . . ?
C16 C15 C20 117.2(2) . . ?
C20 C15 C14 118.8(2) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.1(2) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.3(2) . . ?
C18 C17 H17 120.4 . . ?
O2 C18 C17 124.3(2) . . ?
O2 C18 C19 115.9(2) . . ?
C17 C18 C19 119.8(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 H20 119.3 . . ?
C19 C20 C15 121.4(2) . . ?
C19 C20 H20 119.3 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C14 C15 C16 -179.3(2) . . . . ?
O1 C14 C15 C20 -2.0(4) . . . . ?
O2 C18 C19 C20 178.8(2) . . . . ?
N1 C5 C6 C1 -179.0(2) . . . . ?
N1 C5 C6 C7 0.7(3) . . . . ?
N1 C8 C9 C10 163.6(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C1 C6 C7 C8 178.9(3) . . . . ?
C1 C6 C7 C12 -0.6(5) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C2 C1 C6 C7 179.5(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 N1 179.7(2) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 2.0(4) . . . . ?
C4 C5 C6 C7 -178.3(2) . . . . ?
C5 N1 C8 C7 0.0(3) . . . . ?
C5 N1 C8 C9 -179.9(2) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C5 C6 C7 C12 179.8(2) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
C6 C7 C8 N1 0.4(3) . . . . ?
C6 C7 C8 C9 -179.7(2) . . . . ?
C6 C7 C12 C11 166.5(2) . . . . ?
C6 C7 C12 C14 -71.7(3) . . . . ?
C7 C8 C9 C10 -16.2(4) . . . . ?
C7 C12 C14 O1 -21.9(4) . . . . ?
C7 C12 C14 C15 161.0(2) . . . . ?
C8 N1 C5 C4 178.5(2) . . . . ?
C8 N1 C5 C6 -0.5(3) . . . . ?
C8 C7 C12 C11 -13.0(3) . . . . ?
C8 C7 C12 C14 108.8(3) . . . . ?
C8 C9 C10 C11 46.4(3) . . . . ?
C9 C10 C11 C12 -63.2(3) . . . . ?
C10 C11 C12 C7 43.0(3) . . . . ?
C10 C11 C12 C14 -81.4(3) . . . . ?
C11 C12 C14 O1 100.2(3) . . . . ?
C11 C12 C14 C15 -77.0(3) . . . . ?
C12 C7 C8 N1 180.0(2) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C12 C14 C15 C16 -2.2(4) . . . . ?
C12 C14 C15 C20 175.1(2) . . . . ?
C13 N1 C5 C4 -0.8(4) . . . . ?
C13 N1 C5 C6 -179.8(2) . . . . ?
C13 N1 C8 C7 179.3(2) . . . . ?
C13 N1 C8 C9 -0.5(4) . . . . ?
C14 C15 C16 C17 177.4(2) . . . . ?
C14 C15 C20 C19 -177.9(2) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C15 C20 C19 -0.4(4) . . . . ?
C16 C17 C18 O2 -179.2(2) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C18 C19 C20 -1.1(4) . . . . ?
C18 C19 C20 C15 1.0(4) . . . . ?
C20 C15 C16 C17 0.1(4) . . . . ?
C21 O2 C18 C17 2.5(4) . . . . ?
C21 O2 C18 C19 -177.4(2) . . . . ?

_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_230919_ngh_c076_1a_zlj_0m
_database_code_depnum_ccdc_archive 'CCDC 2296216'
loop_
_audit_author_name
_audit_author_address
p
;Guizhou University
China
;
_audit_update_record             
;
2023-09-20 deposited with the CCDC.	2024-03-19 downloaded from the CCDC.
;
_audit_creation_date             2023-09-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N O2'
_chemical_formula_sum            'C20 H19 N O2'
_chemical_formula_weight         305.36
_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                   9.9529(5)
_cell_length_b                   15.6474(6)
_cell_length_c                   10.0527(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.830(2)
_cell_angle_gamma                90
_cell_volume                     1542.59(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6836
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      27.358
_cell_measurement_theta_min      2.433
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1800 before and 0.0801 after correction.
The Ratio of minimum to maximum transmission is 0.8525.
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.23
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0880
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            30179
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_min         2.434
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ 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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2689
_reflns_number_total             3535
_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 (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3535
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0627
_refine_ls_restrained_S_all      1.128
_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)+(0.0318P)²+1.1843P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1335
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78346(17) 0.38528(11) 0.47104(15) 0.0421(4) Uani 1 1 d . . . . .
N1 N 0.47350(17) 0.30420(11) 0.40543(17) 0.0281(4) Uani 1 1 d . . . . .
C1 C 0.4218(2) 0.07909(13) 0.3477(2) 0.0296(5) Uani 1 1 d . . . . .
H1 H 0.458959 0.027392 0.387733 0.036 Uiso 1 1 calc R U . . .
O2 O 0.97281(15) 0.64733(10) 0.93926(15) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.3194(2) 0.07702(15) 0.2361(2) 0.0349(5) Uani 1 1 d . . . . .
H2 H 0.286209 0.023460 0.199889 0.042 Uiso 1 1 calc R U . . .
C3 C 0.2636(2) 0.15242(15) 0.1755(2) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.193220 0.149134 0.098931 0.046 Uiso 1 1 calc R U . . .
C4 C 0.3088(2) 0.23136(15) 0.2248(2) 0.0340(5) Uani 1 1 d . . . . .
H4 H 0.271075 0.282381 0.182780 0.041 Uiso 1 1 calc R U . . .
C5 C 0.41122(19) 0.23427(13) 0.3376(2) 0.0266(4) Uani 1 1 d . . . . .
C6 C 0.47060(19) 0.15830(12) 0.40138(19) 0.0244(4) Uani 1 1 d . . . . .
C7 C 0.5731(2) 0.18690(12) 0.50995(19) 0.0245(4) Uani 1 1 d . . . . .
C8 C 0.57013(19) 0.27357(13) 0.5080(2) 0.0252(4) Uani 1 1 d . . . . .
C9 C 0.6599(2) 0.31621(12) 0.6230(2) 0.0264(4) Uani 1 1 d . . . . .
H9 H 0.604009 0.339842 0.688151 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7460(2) 0.23744(13) 0.6872(2) 0.0326(5) Uani 1 1 d . . . . .
H10A H 0.839095 0.239775 0.665073 0.039 Uiso 1 1 calc R U . . .
H10B H 0.753271 0.238340 0.786625 0.039 Uiso 1 1 calc R U . . .
C11 C 0.6725(2) 0.15452(13) 0.6285(2) 0.0293(5) Uani 1 1 d . . . . .
H11A H 0.737673 0.113595 0.599608 0.035 Uiso 1 1 calc R U . . .
H11B H 0.624715 0.126477 0.695426 0.035 Uiso 1 1 calc R U . . .
C12 C 0.4349(2) 0.39318(13) 0.3815(2) 0.0361(5) Uani 1 1 d . . . . .
H12A H 0.390347 0.400384 0.287408 0.054 Uiso 1 1 calc R U . . .
H12B H 0.516511 0.429208 0.399188 0.054 Uiso 1 1 calc R U . . .
H12C H 0.371712 0.409929 0.441712 0.054 Uiso 1 1 calc R U . . .
C13 C 0.7541(2) 0.38454(13) 0.5841(2) 0.0269(4) Uani 1 1 d . . . . .
C14 C 0.81143(19) 0.44963(12) 0.68536(19) 0.0238(4) Uani 1 1 d . . . . .
C15 C 0.9023(2) 0.51013(14) 0.6486(2) 0.0308(5) Uani 1 1 d . . . . .
H15 H 0.927067 0.506902 0.561627 0.037 Uiso 1 1 calc R U . . .
C16 C 0.9562(2) 0.57378(14) 0.7350(2) 0.0334(5) Uani 1 1 d . . . . .
H16 H 1.018771 0.613497 0.708463 0.040 Uiso 1 1 calc R U . . .
C17 C 0.91845(19) 0.58000(13) 0.8627(2) 0.0276(4) Uani 1 1 d . . . . .
C18 C 0.82981(19) 0.52069(13) 0.9023(2) 0.0269(4) Uani 1 1 d . . . . .
H18 H 0.804487 0.524539 0.989038 0.032 Uiso 1 1 calc R U . . .
C19 C 0.7781(2) 0.45541(12) 0.8141(2) 0.0257(4) Uani 1 1 d . . . . .
H19 H 0.718930 0.414040 0.842313 0.031 Uiso 1 1 calc R U . . .
C20 C 0.9267(2) 0.66157(15) 1.0649(2) 0.0383(5) Uani 1 1 d . . . . .
H20A H 0.827414 0.668725 1.048388 0.057 Uiso 1 1 calc R U . . .
H20B H 0.969790 0.713259 1.107758 0.057 Uiso 1 1 calc R U . . .
H20C H 0.951336 0.612455 1.124624 0.057 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 C13 1.221(2) . ?
N1 C5 1.379(3) . ?
N1 C8 1.371(3) . ?
N1 C12 1.453(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.381(3) . ?
C1 C6 1.405(3) . ?
O2 C17 1.361(2) . ?
O2 C20 1.433(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.377(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(3) . ?
C5 C6 1.430(3) . ?
C6 C7 1.432(3) . ?
C7 C8 1.357(3) . ?
C7 C11 1.501(3) . ?
C8 C9 1.492(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.575(3) . ?
C9 C13 1.516(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.555(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.484(3) . ?
C14 C15 1.401(3) . ?
C14 C19 1.393(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.369(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.401(3) . ?
C17 C18 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(3) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C5 N1 C12 126.46(17) . . ?
C8 N1 C5 107.03(16) . . ?
C8 N1 C12 126.24(18) . . ?
C2 C1 H1 120.3 . . ?
C2 C1 C6 119.4(2) . . ?
C6 C1 H1 120.3 . . ?
C17 O2 C20 117.57(17) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.1(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(2) . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 129.37(19) . . ?
N1 C5 C6 108.76(17) . . ?
C4 C5 C6 121.87(19) . . ?
C1 C6 C5 118.16(18) . . ?
C1 C6 C7 136.29(19) . . ?
C5 C6 C7 105.54(17) . . ?
C6 C7 C11 141.87(18) . . ?
C8 C7 C6 106.89(18) . . ?
C8 C7 C11 111.01(18) . . ?
N1 C8 C9 132.60(18) . . ?
C7 C8 N1 111.78(18) . . ?
C7 C8 C9 115.29(18) . . ?
C8 C9 H9 110.2 . . ?
C8 C9 C10 100.33(16) . . ?
C8 C9 C13 115.48(17) . . ?
C10 C9 H9 110.2 . . ?
C13 C9 H9 110.2 . . ?
C13 C9 C10 109.93(16) . . ?
C9 C10 H10A 110.1 . . ?
C9 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C11 C10 C9 108.05(16) . . ?
C11 C10 H10A 110.1 . . ?
C11 C10 H10B 110.1 . . ?
C7 C11 C10 102.89(16) . . ?
C7 C11 H11A 111.2 . . ?
C7 C11 H11B 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.1 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 C9 120.23(19) . . ?
O1 C13 C14 120.45(18) . . ?
C14 C13 C9 119.31(17) . . ?
C15 C14 C13 118.24(17) . . ?
C19 C14 C13 123.86(18) . . ?
C19 C14 C15 117.88(18) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.67(19) . . ?
C16 C15 H15 119.2 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.62(19) . . ?
C17 C16 H16 120.2 . . ?
O2 C17 C16 115.43(18) . . ?
O2 C17 C18 124.53(19) . . ?
C18 C17 C16 120.03(19) . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.54(18) . . ?
C19 C18 H18 120.2 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.21(18) . . ?
C18 C19 H19 119.4 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C13 C14 C15 -1.6(3) . . . . ?
O1 C13 C14 C19 177.0(2) . . . . ?
N1 C5 C6 C1 -179.85(17) . . . . ?
N1 C5 C6 C7 -0.8(2) . . . . ?
N1 C8 C9 C10 -176.6(2) . . . . ?
N1 C8 C9 C13 -58.5(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C1 C6 C7 C8 179.5(2) . . . . ?
C1 C6 C7 C11 -7.0(4) . . . . ?
O2 C17 C18 C19 178.54(18) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C2 C1 C6 C7 -178.6(2) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 N1 179.9(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C4 C5 C6 C7 178.51(18) . . . . ?
C5 N1 C8 C7 -0.1(2) . . . . ?
C5 N1 C8 C9 -172.9(2) . . . . ?
C5 C6 C7 C8 0.7(2) . . . . ?
C5 C6 C7 C11 174.2(2) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C7 C8 N1 -0.3(2) . . . . ?
C6 C7 C8 C9 173.80(15) . . . . ?
C6 C7 C11 C10 178.5(2) . . . . ?
C7 C8 C9 C10 10.8(2) . . . . ?
C7 C8 C9 C13 128.85(19) . . . . ?
C8 N1 C5 C4 -178.6(2) . . . . ?
C8 N1 C5 C6 0.6(2) . . . . ?
C8 C7 C11 C10 -8.1(2) . . . . ?
C8 C9 C10 C11 -15.1(2) . . . . ?
C8 C9 C13 O1 -21.4(3) . . . . ?
C8 C9 C13 C14 159.46(17) . . . . ?
C9 C10 C11 C7 14.5(2) . . . . ?
C9 C13 C14 C15 177.60(18) . . . . ?
C9 C13 C14 C19 -3.9(3) . . . . ?
C10 C9 C13 O1 91.2(2) . . . . ?
C10 C9 C13 C14 -88.0(2) . . . . ?
C11 C7 C8 N1 -176.05(16) . . . . ?
C11 C7 C8 C9 -1.9(2) . . . . ?
C12 N1 C5 C4 7.0(3) . . . . ?
C12 N1 C5 C6 -173.77(19) . . . . ?
C12 N1 C8 C7 174.21(19) . . . . ?
C12 N1 C8 C9 1.4(3) . . . . ?
C13 C9 C10 C11 -137.23(17) . . . . ?
C13 C14 C15 C16 177.94(19) . . . . ?
C13 C14 C19 C18 -176.59(18) . . . . ?
C14 C15 C16 C17 -1.1(3) . . . . ?
C15 C14 C19 C18 2.0(3) . . . . ?
C15 C16 C17 O2 -177.39(19) . . . . ?
C15 C16 C17 C18 1.6(3) . . . . ?
C16 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?
C20 O2 C17 C16 173.82(19) . . . . ?
C20 O2 C17 C18 -5.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
