# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_231031_jby_2_16_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2325792'
loop_
_audit_author_name
_audit_author_address
'Boyang Jiang' 'Zhejiang University'
_audit_update_record             
;
2024-01-16 deposited with the CCDC.	2024-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-02
_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         'C24 H27 N O3'
_chemical_formula_sum            'C24 H27 N O3'
_chemical_formula_weight         377.46
_chemical_absolute_configuration ad
_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           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                   7.9599(3)
_cell_length_b                   11.3575(5)
_cell_length_c                   11.6102(5)
_cell_angle_alpha                86.482(2)
_cell_angle_beta                 83.174(2)
_cell_angle_gamma                83.793(2)
_cell_volume                     1034.81(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9388
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.611
_cell_measurement_theta_min      5.676
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.401
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0608 after correction.
The Ratio of minimum to maximum transmission is 0.9199.
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    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            66610
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.678
_diffrn_reflns_theta_min         3.339
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'zju 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         0.908
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                8795
_reflns_number_total             8998
_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       'Bruker Instrument Service vV6.2.14'
_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         0.156
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 4052 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     511
_refine_ls_number_reflns         8998
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.079
_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)+(0.0402P)²+0.1778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0850
_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:
 C18(H18), C42(H42)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16), C21(H21),
 C22(H22), C31(H31), C32(H32), C33(H33), C34(H34), C38(H38), C39(H39), C40(H40),
  C45(H45), C46(H46)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C43(H43A,H43B,
 H43C), C44(H44A,H44B,H44C), C48(H48A,H48B,H48C)
;
_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 1.0765(2) 0.16453(13) 0.13587(12) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.9377(2) 0.34207(15) 0.18080(14) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.9803(3) 0.39348(19) 0.06327(18) 0.0354(4) Uani 1 1 d . . . . .
H1A H 0.926236 0.354242 0.005503 0.042 Uiso 1 1 calc R U . . .
H1B H 1.104864 0.386310 0.041382 0.042 Uiso 1 1 calc R U . . .
O2 O 0.2591(2) 0.46706(14) 0.22241(14) 0.0422(4) Uani 1 1 d . . . . .
C2 C 0.9085(3) 0.5233(2) 0.0719(2) 0.0391(5) Uani 1 1 d . . . . .
H2A H 0.994728 0.572163 0.093331 0.047 Uiso 1 1 calc R U . . .
H2B H 0.869039 0.555848 -0.002387 0.047 Uiso 1 1 calc R U . . .
O3 O 0.3985(2) 0.40047(13) 0.37263(13) 0.0374(3) Uani 1 1 d . . . . .
C3 C 0.7601(3) 0.5190(2) 0.1677(2) 0.0394(5) Uani 1 1 d . . . . .
H3A H 0.728706 0.597355 0.201533 0.047 Uiso 1 1 calc R U . . .
H3B H 0.659192 0.492811 0.138145 0.047 Uiso 1 1 calc R U . . .
C4 C 0.8314(3) 0.42814(18) 0.25598(18) 0.0318(4) Uani 1 1 d . . . . .
H4A H 0.900527 0.464743 0.306800 0.038 Uiso 1 1 calc R U . . .
H4B H 0.739439 0.390274 0.304620 0.038 Uiso 1 1 calc R U . . .
C5 C 0.9906(2) 0.22851(17) 0.20718(16) 0.0260(4) Uani 1 1 d . . . . .
C6 C 0.9393(2) 0.18137(15) 0.32892(15) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.9975(2) 0.22760(17) 0.42416(17) 0.0289(4) Uani 1 1 d . . . . .
H7 H 1.066970 0.291178 0.412347 0.035 Uiso 1 1 calc R U . . .
C8 C 0.9542(2) 0.18117(18) 0.53563(17) 0.0300(4) Uani 1 1 d . . . . .
H8 H 0.996653 0.211540 0.599688 0.036 Uiso 1 1 calc R U . . .
C9 C 0.8495(2) 0.09074(18) 0.55376(16) 0.0288(4) Uani 1 1 d . . . . .
H9 H 0.817258 0.060566 0.630406 0.035 Uiso 1 1 calc R U . . .
C10 C 0.7915(2) 0.04416(16) 0.46001(16) 0.0251(3) Uani 1 1 d . . . . .
H10 H 0.720254 -0.018353 0.473009 0.030 Uiso 1 1 calc R U . . .
C11 C 0.8364(2) 0.08769(15) 0.34685(14) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.7662(2) 0.03581(14) 0.24884(14) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.8493(2) -0.06694(15) 0.19863(15) 0.0223(3) Uani 1 1 d . . . . .
C14 C 0.7704(2) -0.11722(16) 0.11485(15) 0.0262(4) Uani 1 1 d . . . . .
H14 H 0.823509 -0.187939 0.081188 0.031 Uiso 1 1 calc R U . . .
C15 C 0.6172(2) -0.06712(17) 0.07944(15) 0.0268(4) Uani 1 1 d . . . . .
H15 H 0.566135 -0.104034 0.023109 0.032 Uiso 1 1 calc R U . . .
C16 C 0.5387(2) 0.03676(17) 0.12619(15) 0.0250(3) Uani 1 1 d . . . . .
H16 H 0.435044 0.072214 0.100623 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6123(2) 0.08969(15) 0.21142(14) 0.0216(3) Uani 1 1 d . . . . .
C18 C 1.0206(2) -0.12154(16) 0.23308(17) 0.0264(4) Uani 1 1 d . . . . .
H18 H 1.068970 -0.060096 0.273742 0.032 Uiso 1 1 calc R U . . .
C19 C 1.1471(3) -0.1546(2) 0.1277(2) 0.0400(5) Uani 1 1 d . . . . .
H19A H 1.257528 -0.184062 0.153492 0.060 Uiso 1 1 calc R U . . .
H19B H 1.160028 -0.084394 0.075216 0.060 Uiso 1 1 calc R U . . .
H19C H 1.105060 -0.216419 0.086854 0.060 Uiso 1 1 calc R U . . .
C20 C 1.0013(3) -0.2283(2) 0.3187(2) 0.0410(5) Uani 1 1 d . . . . .
H20A H 0.950749 -0.289571 0.282356 0.062 Uiso 1 1 calc R U . . .
H20B H 0.927417 -0.203560 0.388483 0.062 Uiso 1 1 calc R U . . .
H20C H 1.113317 -0.260291 0.340094 0.062 Uiso 1 1 calc R U . . .
C21 C 0.5316(2) 0.19974(16) 0.26222(15) 0.0231(3) Uani 1 1 d . . . . .
H21 H 0.559510 0.215471 0.336713 0.028 Uiso 1 1 calc R U . . .
C22 C 0.4226(2) 0.27999(17) 0.21364(17) 0.0279(4) Uani 1 1 d . . . . .
H22 H 0.389806 0.264618 0.140390 0.034 Uiso 1 1 calc R U . . .
C23 C 0.3503(2) 0.39131(17) 0.26780(16) 0.0261(4) Uani 1 1 d . . . . .
C24 C 0.3342(5) 0.5089(2) 0.4287(2) 0.0581(8) Uani 1 1 d . . . . .
H24A H 0.372165 0.576824 0.380157 0.087 Uiso 1 1 calc R U . . .
H24B H 0.377264 0.508147 0.504439 0.087 Uiso 1 1 calc R U . . .
H24C H 0.209643 0.515365 0.439605 0.087 Uiso 1 1 calc R U . . .
N2 N 0.4678(2) -0.31962(14) 0.79797(13) 0.0278(3) Uani 1 1 d . . . . .
O4 O 0.55432(19) -0.13977(13) 0.81195(12) 0.0331(3) Uani 1 1 d . . . . .
O5 O -0.0139(3) -0.41193(18) 0.59931(17) 0.0593(5) Uani 1 1 d . . . . .
O6 O -0.1480(2) -0.46517(14) 0.77098(16) 0.0450(4) Uani 1 1 d . . . . .
C25 C 0.4843(3) -0.35225(19) 0.92129(17) 0.0327(4) Uani 1 1 d . . . . .
H25A H 0.411016 -0.296348 0.972466 0.039 Uiso 1 1 calc R U . . .
H25B H 0.603620 -0.353003 0.937763 0.039 Uiso 1 1 calc R U . . .
C26 C 0.4259(3) -0.4763(2) 0.9380(2) 0.0422(5) Uani 1 1 d . . . . .
H26A H 0.366848 -0.489401 1.017031 0.051 Uiso 1 1 calc R U . . .
H26B H 0.523438 -0.537831 0.925270 0.051 Uiso 1 1 calc R U . . .
C27 C 0.3041(3) -0.4781(2) 0.8457(2) 0.0404(5) Uani 1 1 d . . . . .
H27A H 0.291531 -0.560269 0.826808 0.049 Uiso 1 1 calc R U . . .
H27B H 0.190574 -0.437671 0.871645 0.049 Uiso 1 1 calc R U . . .
C28 C 0.3920(3) -0.41041(17) 0.74215(17) 0.0304(4) Uani 1 1 d . . . . .
H28A H 0.480413 -0.462885 0.697419 0.036 Uiso 1 1 calc R U . . .
H28B H 0.309233 -0.373992 0.689822 0.036 Uiso 1 1 calc R U . . .
C29 C 0.5000(2) -0.21156(16) 0.75389(15) 0.0240(3) Uani 1 1 d . . . . .
C30 C 0.4666(2) -0.18032(15) 0.63017(15) 0.0225(3) Uani 1 1 d . . . . .
C31 C 0.5653(2) -0.23891(17) 0.53887(16) 0.0278(4) Uani 1 1 d . . . . .
H31 H 0.651580 -0.300230 0.554915 0.033 Uiso 1 1 calc R U . . .
C32 C 0.5370(3) -0.20735(18) 0.42491(17) 0.0299(4) Uani 1 1 d . . . . .
H32 H 0.603916 -0.247223 0.362990 0.036 Uiso 1 1 calc R U . . .
C33 C 0.4115(3) -0.11798(18) 0.40112(16) 0.0295(4) Uani 1 1 d . . . . .
H33 H 0.392632 -0.096570 0.322969 0.035 Uiso 1 1 calc R U . . .
C34 C 0.3130(2) -0.05943(17) 0.49159(16) 0.0262(4) Uani 1 1 d . . . . .
H34 H 0.227218 0.002001 0.474811 0.031 Uiso 1 1 calc R U . . .
C35 C 0.3392(2) -0.09036(15) 0.60689(15) 0.0215(3) Uani 1 1 d . . . . .
C36 C 0.2220(2) -0.03283(15) 0.70381(14) 0.0217(3) Uani 1 1 d . . . . .
C37 C 0.2604(2) 0.06867(16) 0.75369(15) 0.0244(3) Uani 1 1 d . . . . .
C38 C 0.1452(3) 0.11702(17) 0.84329(17) 0.0304(4) Uani 1 1 d . . . . .
H38 H 0.170136 0.185419 0.878565 0.037 Uiso 1 1 calc R U . . .
C39 C -0.0046(3) 0.06749(18) 0.88187(17) 0.0314(4) Uani 1 1 d . . . . .
H39 H -0.081705 0.102924 0.941837 0.038 Uiso 1 1 calc R U . . .
C40 C -0.0419(2) -0.03327(17) 0.83320(16) 0.0272(4) Uani 1 1 d . . . . .
H40 H -0.144582 -0.067070 0.859502 0.033 Uiso 1 1 calc R U . . .
C41 C 0.0723(2) -0.08545(15) 0.74488(15) 0.0230(3) Uani 1 1 d . . . . .
C42 C 0.4226(2) 0.12504(17) 0.71199(16) 0.0277(4) Uani 1 1 d . . . . .
H42 H 0.502721 0.063805 0.669957 0.033 Uiso 1 1 calc R U . . .
C43 C 0.3892(3) 0.2296(2) 0.6251(2) 0.0416(5) Uani 1 1 d . . . . .
H43A H 0.338837 0.202535 0.559650 0.062 Uiso 1 1 calc R U . . .
H43B H 0.496638 0.261815 0.596573 0.062 Uiso 1 1 calc R U . . .
H43C H 0.310597 0.291492 0.663502 0.062 Uiso 1 1 calc R U . . .
C44 C 0.5113(3) 0.1633(2) 0.81152(19) 0.0362(4) Uani 1 1 d . . . . .
H44A H 0.438498 0.226433 0.852228 0.054 Uiso 1 1 calc R U . . .
H44B H 0.619684 0.192542 0.780150 0.054 Uiso 1 1 calc R U . . .
H44C H 0.532377 0.095275 0.865899 0.054 Uiso 1 1 calc R U . . .
C45 C 0.0374(2) -0.19547(16) 0.69648(16) 0.0254(4) Uani 1 1 d . . . . .
H45 H 0.087601 -0.210722 0.619769 0.030 Uiso 1 1 calc R U . . .
C46 C -0.0585(2) -0.27594(17) 0.75040(17) 0.0282(4) Uani 1 1 d . . . . .
H46 H -0.119599 -0.260792 0.824251 0.034 Uiso 1 1 calc R U . . .
C47 C -0.0701(2) -0.38785(18) 0.69637(19) 0.0314(4) Uani 1 1 d . . . . .
C48 C -0.1498(4) -0.5823(2) 0.7297(3) 0.0584(7) Uani 1 1 d . . . . .
H48A H -0.202403 -0.576338 0.657113 0.088 Uiso 1 1 calc R U . . .
H48B H -0.215302 -0.630266 0.788113 0.088 Uiso 1 1 calc R U . . .
H48C H -0.032944 -0.619893 0.715790 0.088 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 1.230(2) . ?
N1 C1 1.467(2) . ?
N1 C4 1.478(3) . ?
N1 C5 1.342(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.527(3) . ?
O2 C23 1.202(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(3) . ?
O3 C23 1.332(2) . ?
O3 C24 1.444(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.506(3) . ?
C6 C7 1.399(2) . ?
C6 C11 1.403(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.395(2) . ?
C11 C12 1.503(2) . ?
C12 C13 1.401(2) . ?
C12 C17 1.413(2) . ?
C13 C14 1.399(2) . ?
C13 C18 1.523(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.384(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.404(2) . ?
C17 C21 1.466(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.528(3) . ?
C18 C20 1.529(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C22 1.336(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.476(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N2 C25 1.474(2) . ?
N2 C28 1.468(2) . ?
N2 C29 1.339(3) . ?
O4 C29 1.233(2) . ?
O5 C47 1.198(3) . ?
O6 C47 1.343(3) . ?
O6 C48 1.444(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.525(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.531(3) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.527(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.506(2) . ?
C30 C31 1.400(2) . ?
C30 C35 1.397(2) . ?
C31 H31 0.9500 . ?
C31 C32 1.388(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.392(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.397(2) . ?
C35 C36 1.508(2) . ?
C36 C37 1.399(2) . ?
C36 C41 1.410(2) . ?
C37 C38 1.400(3) . ?
C37 C42 1.518(3) . ?
C38 H38 0.9500 . ?
C38 C39 1.388(3) . ?
C39 H39 0.9500 . ?
C39 C40 1.382(3) . ?
C40 H40 0.9500 . ?
C40 C41 1.402(2) . ?
C41 C45 1.467(3) . ?
C42 H42 1.0000 . ?
C42 C43 1.533(3) . ?
C42 C44 1.531(3) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45 0.9500 . ?
C45 C46 1.333(3) . ?
C46 H46 0.9500 . ?
C46 C47 1.468(3) . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 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
C1 N1 C4 111.73(16) . . ?
C5 N1 C1 120.06(16) . . ?
C5 N1 C4 128.18(16) . . ?
N1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
N1 C1 C2 103.55(17) . . ?
H1A C1 H1B 109.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.40(17) . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C23 O3 C24 115.28(17) . . ?
C2 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C4 C3 C2 102.54(17) . . ?
C4 C3 H3A 111.3 . . ?
C4 C3 H3B 111.3 . . ?
N1 C4 C3 102.25(16) . . ?
N1 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
O1 C5 N1 122.17(18) . . ?
O1 C5 C6 120.81(17) . . ?
N1 C5 C6 117.02(16) . . ?
C7 C6 C5 120.71(16) . . ?
C7 C6 C11 119.59(16) . . ?
C11 C6 C5 119.68(15) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.38(18) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.12(16) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 119.93(17) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.97(17) . . ?
C11 C10 H10 119.5 . . ?
C6 C11 C12 122.35(15) . . ?
C10 C11 C6 118.98(15) . . ?
C10 C11 C12 118.62(15) . . ?
C13 C12 C11 120.27(15) . . ?
C13 C12 C17 120.77(15) . . ?
C17 C12 C11 118.92(14) . . ?
C12 C13 C18 121.22(15) . . ?
C14 C13 C12 117.77(16) . . ?
C14 C13 C18 121.01(16) . . ?
C13 C14 H14 119.0 . . ?
C15 C14 C13 122.08(17) . . ?
C15 C14 H14 119.0 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 119.95(16) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 119.95(17) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C21 119.61(14) . . ?
C16 C17 C12 119.41(16) . . ?
C16 C17 C21 120.97(16) . . ?
C13 C18 H18 107.3 . . ?
C13 C18 C19 112.25(16) . . ?
C13 C18 C20 111.61(16) . . ?
C19 C18 H18 107.3 . . ?
C19 C18 C20 110.86(17) . . ?
C20 C18 H18 107.3 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21 116.9 . . ?
C22 C21 C17 126.16(16) . . ?
C22 C21 H21 116.9 . . ?
C21 C22 H22 118.3 . . ?
C21 C22 C23 123.45(17) . . ?
C23 C22 H22 118.3 . . ?
O2 C23 O3 122.95(18) . . ?
O2 C23 C22 124.12(18) . . ?
O3 C23 C22 112.92(15) . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 N2 C25 111.81(16) . . ?
C29 N2 C25 120.14(16) . . ?
C29 N2 C28 127.48(16) . . ?
C47 O6 C48 115.7(2) . . ?
N2 C25 H25A 111.0 . . ?
N2 C25 H25B 111.0 . . ?
N2 C25 C26 103.74(17) . . ?
H25A C25 H25B 109.0 . . ?
C26 C25 H25A 111.0 . . ?
C26 C25 H25B 111.0 . . ?
C25 C26 H26A 111.0 . . ?
C25 C26 H26B 111.0 . . ?
C25 C26 C27 103.57(17) . . ?
H26A C26 H26B 109.0 . . ?
C27 C26 H26A 111.0 . . ?
C27 C26 H26B 111.0 . . ?
C26 C27 H27A 111.2 . . ?
C26 C27 H27B 111.2 . . ?
H27A C27 H27B 109.1 . . ?
C28 C27 C26 102.68(18) . . ?
C28 C27 H27A 111.2 . . ?
C28 C27 H27B 111.2 . . ?
N2 C28 C27 102.51(16) . . ?
N2 C28 H28A 111.3 . . ?
N2 C28 H28B 111.3 . . ?
C27 C28 H28A 111.3 . . ?
C27 C28 H28B 111.3 . . ?
H28A C28 H28B 109.2 . . ?
N2 C29 C30 117.47(15) . . ?
O4 C29 N2 121.64(17) . . ?
O4 C29 C30 120.89(17) . . ?
C31 C30 C29 120.27(16) . . ?
C35 C30 C29 119.53(15) . . ?
C35 C30 C31 120.17(16) . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 119.94(18) . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 119.9 . . ?
C33 C32 C31 120.23(17) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 H33 120.0 . . ?
C32 C33 C34 120.08(17) . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.48(17) . . ?
C35 C34 H34 119.8 . . ?
C30 C35 C36 121.14(15) . . ?
C34 C35 C30 119.10(16) . . ?
C34 C35 C36 119.61(15) . . ?
C37 C36 C35 121.56(15) . . ?
C37 C36 C41 120.37(15) . . ?
C41 C36 C35 118.06(15) . . ?
C36 C37 C38 118.24(17) . . ?
C36 C37 C42 121.01(15) . . ?
C38 C37 C42 120.75(16) . . ?
C37 C38 H38 119.2 . . ?
C39 C38 C37 121.62(18) . . ?
C39 C38 H38 119.2 . . ?
C38 C39 H39 119.9 . . ?
C40 C39 C38 120.12(17) . . ?
C40 C39 H39 119.9 . . ?
C39 C40 H40 120.1 . . ?
C39 C40 C41 119.78(17) . . ?
C41 C40 H40 120.1 . . ?
C36 C41 C45 120.08(15) . . ?
C40 C41 C36 119.82(17) . . ?
C40 C41 C45 120.10(16) . . ?
C37 C42 H42 107.3 . . ?
C37 C42 C43 111.11(16) . . ?
C37 C42 C44 113.01(16) . . ?
C43 C42 H42 107.3 . . ?
C44 C42 H42 107.3 . . ?
C44 C42 C43 110.56(17) . . ?
C42 C43 H43A 109.5 . . ?
C42 C43 H43B 109.5 . . ?
C42 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C41 C45 H45 117.1 . . ?
C46 C45 C41 125.90(16) . . ?
C46 C45 H45 117.0 . . ?
C45 C46 H46 119.8 . . ?
C45 C46 C47 120.40(17) . . ?
C47 C46 H46 119.8 . . ?
O5 C47 O6 122.4(2) . . ?
O5 C47 C46 125.9(2) . . ?
O6 C47 C46 111.65(18) . . ?
O6 C48 H48A 109.5 . . ?
O6 C48 H48B 109.5 . . ?
O6 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 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 C5 C6 C7 116.1(2) . . . . ?
O1 C5 C6 C11 -61.9(2) . . . . ?
N1 C1 C2 C3 -28.4(2) . . . . ?
N1 C5 C6 C7 -64.2(2) . . . . ?
N1 C5 C6 C11 117.70(19) . . . . ?
C1 N1 C4 C3 19.4(2) . . . . ?
C1 N1 C5 O1 0.7(3) . . . . ?
C1 N1 C5 C6 -178.93(17) . . . . ?
C1 C2 C3 C4 40.4(2) . . . . ?
C2 C3 C4 N1 -36.2(2) . . . . ?
C4 N1 C1 C2 5.6(2) . . . . ?
C4 N1 C5 O1 178.49(19) . . . . ?
C4 N1 C5 C6 -1.1(3) . . . . ?
C5 N1 C1 C2 -176.26(18) . . . . ?
C5 N1 C4 C3 -158.6(2) . . . . ?
C5 C6 C7 C8 -177.89(18) . . . . ?
C5 C6 C11 C10 179.28(16) . . . . ?
C5 C6 C11 C12 -3.4(2) . . . . ?
C6 C7 C8 C9 -1.7(3) . . . . ?
C6 C11 C12 C13 96.9(2) . . . . ?
C6 C11 C12 C17 -85.5(2) . . . . ?
C7 C6 C11 C10 1.2(2) . . . . ?
C7 C6 C11 C12 178.52(16) . . . . ?
C7 C8 C9 C10 1.8(3) . . . . ?
C8 C9 C10 C11 -0.4(3) . . . . ?
C9 C10 C11 C6 -1.1(3) . . . . ?
C9 C10 C11 C12 -178.49(16) . . . . ?
C10 C11 C12 C13 -85.8(2) . . . . ?
C10 C11 C12 C17 91.83(19) . . . . ?
C11 C6 C7 C8 0.2(3) . . . . ?
C11 C12 C13 C14 174.44(15) . . . . ?
C11 C12 C13 C18 -6.1(2) . . . . ?
C11 C12 C17 C16 -175.08(15) . . . . ?
C11 C12 C17 C21 4.8(2) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C12 C13 C18 C19 -134.04(18) . . . . ?
C12 C13 C18 C20 100.8(2) . . . . ?
C12 C17 C21 C22 156.98(18) . . . . ?
C13 C12 C17 C16 2.6(2) . . . . ?
C13 C12 C17 C21 -177.59(15) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C13 C18 C19 45.4(2) . . . . ?
C14 C13 C18 C20 -79.8(2) . . . . ?
C14 C15 C16 C17 -1.5(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C15 C16 C17 C21 179.97(16) . . . . ?
C16 C17 C21 C22 -23.2(3) . . . . ?
C17 C12 C13 C14 -3.2(2) . . . . ?
C17 C12 C13 C18 176.26(16) . . . . ?
C17 C21 C22 C23 -177.79(17) . . . . ?
C18 C13 C14 C15 -177.94(17) . . . . ?
C21 C22 C23 O2 175.9(2) . . . . ?
C21 C22 C23 O3 -3.2(3) . . . . ?
C24 O3 C23 O2 -0.3(3) . . . . ?
C24 O3 C23 C22 178.8(2) . . . . ?
N2 C25 C26 C27 -26.9(2) . . . . ?
N2 C29 C30 C31 -67.0(2) . . . . ?
N2 C29 C30 C35 114.61(19) . . . . ?
O4 C29 C30 C31 113.3(2) . . . . ?
O4 C29 C30 C35 -65.2(2) . . . . ?
C25 N2 C28 C27 19.9(2) . . . . ?
C25 N2 C29 O4 4.8(3) . . . . ?
C25 N2 C29 C30 -175.01(16) . . . . ?
C25 C26 C27 C28 39.2(2) . . . . ?
C26 C27 C28 N2 -35.8(2) . . . . ?
C28 N2 C25 C26 4.3(2) . . . . ?
C28 N2 C29 O4 175.35(18) . . . . ?
C28 N2 C29 C30 -4.4(3) . . . . ?
C29 N2 C25 C26 176.30(18) . . . . ?
C29 N2 C28 C27 -151.29(19) . . . . ?
C29 C30 C31 C32 -178.20(18) . . . . ?
C29 C30 C35 C34 177.96(16) . . . . ?
C29 C30 C35 C36 -6.6(3) . . . . ?
C30 C31 C32 C33 0.1(3) . . . . ?
C30 C35 C36 C37 91.1(2) . . . . ?
C30 C35 C36 C41 -87.8(2) . . . . ?
C31 C30 C35 C34 -0.5(3) . . . . ?
C31 C30 C35 C36 174.96(16) . . . . ?
C31 C32 C33 C34 -0.1(3) . . . . ?
C32 C33 C34 C35 -0.2(3) . . . . ?
C33 C34 C35 C30 0.4(3) . . . . ?
C33 C34 C35 C36 -175.05(17) . . . . ?
C34 C35 C36 C37 -93.5(2) . . . . ?
C34 C35 C36 C41 87.6(2) . . . . ?
C35 C30 C31 C32 0.2(3) . . . . ?
C35 C36 C37 C38 179.97(16) . . . . ?
C35 C36 C37 C42 -0.1(2) . . . . ?
C35 C36 C41 C40 -178.64(15) . . . . ?
C35 C36 C41 C45 2.3(2) . . . . ?
C36 C37 C38 C39 -0.7(3) . . . . ?
C36 C37 C42 C43 97.6(2) . . . . ?
C36 C37 C42 C44 -137.41(18) . . . . ?
C36 C41 C45 C46 154.28(19) . . . . ?
C37 C36 C41 C40 2.4(2) . . . . ?
C37 C36 C41 C45 -176.70(16) . . . . ?
C37 C38 C39 C40 1.2(3) . . . . ?
C38 C37 C42 C43 -82.4(2) . . . . ?
C38 C37 C42 C44 42.6(2) . . . . ?
C38 C39 C40 C41 0.1(3) . . . . ?
C39 C40 C41 C36 -1.9(3) . . . . ?
C39 C40 C41 C45 177.20(17) . . . . ?
C40 C41 C45 C46 -24.8(3) . . . . ?
C41 C36 C37 C38 -1.1(2) . . . . ?
C41 C36 C37 C42 178.85(16) . . . . ?
C41 C45 C46 C47 -174.15(17) . . . . ?
C42 C37 C38 C39 179.36(18) . . . . ?
C45 C46 C47 O5 -8.3(3) . . . . ?
C45 C46 C47 O6 169.53(18) . . . . ?
C48 O6 C47 O5 4.1(3) . . . . ?
C48 O6 C47 C46 -173.8(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_231031_jby_2_cooh_0m
_database_code_depnum_ccdc_archive 'CCDC 2325793'
loop_
_audit_author_name
_audit_author_address
'Boyang Jiang' 'Zhejiang University'
_audit_update_record             
;
2024-01-16 deposited with the CCDC.	2024-05-12 downloaded from the CCDC.
;
_audit_creation_date             2023-11-02
_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 H23 N O3'
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_chemical_absolute_configuration ad
_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      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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.6551(4)
_cell_length_b                   10.6157(4)
_cell_length_c                   19.6488(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1805.33(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9858
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.568
_cell_measurement_theta_min      3.914
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.422
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1187 before and 0.0542 after correction.
The Ratio of minimum to maximum transmission is 0.9024.
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    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.15
_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  0.0307
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31307
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.778
_diffrn_reflns_theta_min         3.915
_diffrn_ambient_temperature      170.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'zju 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         0.745
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                4035
_reflns_number_total             4147
_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       'Bruker Instrument Service vV6.2.14'
_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         0.121
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1712 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.092
_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)+(0.0423P)²+0.2028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0767
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.41884(16) 0.44059(14) 0.43029(6) 0.0500(3) Uani 1 1 d . . . . .
N1 N 0.62002(14) 0.60279(11) 0.73734(6) 0.0267(2) Uani 1 1 d . . . . .
C1 C 0.68757(18) 0.50677(14) 0.78272(7) 0.0313(3) Uani 1 1 d . . . . .
H1A H 0.784396 0.472094 0.763516 0.038 Uiso 1 1 calc R U . . .
H1B H 0.614106 0.436953 0.790999 0.038 Uiso 1 1 calc R U . . .
O2 O 0.58556(14) 0.45713(13) 0.51458(6) 0.0406(3) Uani 1 1 d . . . . .
H2 H 0.582801 0.462156 0.557228 0.061 Uiso 1 1 calc R U . . .
C2 C 0.7186(2) 0.58077(16) 0.84760(8) 0.0385(4) Uani 1 1 d . . . . .
H2A H 0.819603 0.624327 0.845549 0.046 Uiso 1 1 calc R U . . .
H2B H 0.716264 0.525296 0.888094 0.046 Uiso 1 1 calc R U . . .
O3 O 0.61519(13) 0.47134(10) 0.64756(5) 0.0328(2) Uani 1 1 d . . . . .
C3 C 0.5854(2) 0.67473(16) 0.84868(8) 0.0376(4) Uani 1 1 d . . . . .
H3A H 0.487721 0.633764 0.862746 0.045 Uiso 1 1 calc R U . . .
H3B H 0.607462 0.745921 0.879733 0.045 Uiso 1 1 calc R U . . .
C4 C 0.5777(2) 0.71830(14) 0.77523(8) 0.0331(3) Uani 1 1 d . . . . .
H4A H 0.472424 0.747118 0.763139 0.040 Uiso 1 1 calc R U . . .
H4B H 0.652123 0.787208 0.766426 0.040 Uiso 1 1 calc R U . . .
C5 C 0.59154(15) 0.57813(12) 0.67199(7) 0.0247(3) Uani 1 1 d . . . . .
C6 C 0.53669(15) 0.68312(12) 0.62726(7) 0.0233(3) Uani 1 1 d . . . . .
C7 C 0.62382(17) 0.79328(14) 0.62212(7) 0.0279(3) Uani 1 1 d . . . . .
H7 H 0.711367 0.804430 0.650648 0.034 Uiso 1 1 calc R U . . .
C8 C 0.58454(18) 0.88653(14) 0.57605(7) 0.0306(3) Uani 1 1 d . . . . .
H8 H 0.644920 0.961024 0.572815 0.037 Uiso 1 1 calc R U . . .
C9 C 0.45624(19) 0.87036(14) 0.53461(8) 0.0323(3) Uani 1 1 d . . . . .
H9 H 0.429289 0.933463 0.502455 0.039 Uiso 1 1 calc R U . . .
C10 C 0.36719(17) 0.76199(14) 0.54011(7) 0.0284(3) Uani 1 1 d . . . . .
H10 H 0.278231 0.752588 0.512242 0.034 Uiso 1 1 calc R U . . .
C11 C 0.40628(15) 0.66669(12) 0.58591(6) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.30206(15) 0.55411(12) 0.59033(6) 0.0224(3) Uani 1 1 d . . . . .
C13 C 0.31322(17) 0.45832(13) 0.54131(7) 0.0275(3) Uani 1 1 d . . . . .
C14 C 0.2025(2) 0.36326(14) 0.53820(8) 0.0349(3) Uani 1 1 d . . . . .
H14 H 0.208865 0.300406 0.503905 0.042 Uiso 1 1 calc R U . . .
C15 C 0.0835(2) 0.36034(14) 0.58487(9) 0.0378(4) Uani 1 1 d . . . . .
H15 H 0.007875 0.295617 0.582784 0.045 Uiso 1 1 calc R U . . .
C16 C 0.07482(17) 0.45213(14) 0.63478(8) 0.0329(3) Uani 1 1 d . . . . .
H16 H -0.005955 0.448225 0.667450 0.039 Uiso 1 1 calc R U . . .
C17 C 0.18216(15) 0.55051(12) 0.63828(7) 0.0248(3) Uani 1 1 d . . . . .
C18 C 0.44265(19) 0.45333(14) 0.49037(8) 0.0340(3) Uani 1 1 d . . . . .
C19 C 0.16478(16) 0.65091(15) 0.69293(7) 0.0297(3) Uani 1 1 d . . . . .
H19 H 0.252316 0.711608 0.687653 0.036 Uiso 1 1 calc R U . . .
C20 C 0.1755(2) 0.5940(2) 0.76442(8) 0.0475(4) Uani 1 1 d . . . . .
H20A H 0.088498 0.536490 0.771714 0.071 Uiso 1 1 calc R U . . .
H20B H 0.172039 0.661613 0.798352 0.071 Uiso 1 1 calc R U . . .
H20C H 0.272792 0.547546 0.768924 0.071 Uiso 1 1 calc R U . . .
C21 C 0.0147(2) 0.72438(18) 0.68382(11) 0.0472(4) Uani 1 1 d . . . . .
H21A H 0.014536 0.765325 0.639114 0.071 Uiso 1 1 calc R U . . .
H21B H 0.006430 0.788501 0.719514 0.071 Uiso 1 1 calc R U . . .
H21C H -0.073224 0.666522 0.686965 0.071 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 C18 1.2059(18) . ?
N1 C1 1.4751(17) . ?
N1 C4 1.4805(18) . ?
N1 C5 1.3335(18) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.521(2) . ?
O2 H2 0.8400 . ?
O2 C18 1.326(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.525(3) . ?
O3 C5 1.2481(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.517(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.4967(18) . ?
C6 C7 1.3951(19) . ?
C6 C11 1.4017(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3957(18) . ?
C11 C12 1.4997(18) . ?
C12 C13 1.4039(18) . ?
C12 C17 1.4021(19) . ?
C13 C14 1.393(2) . ?
C13 C18 1.503(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3995(19) . ?
C17 C19 1.5205(19) . ?
C19 H19 1.0000 . ?
C19 C20 1.532(2) . ?
C19 C21 1.526(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
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
C1 N1 C4 111.50(11) . . ?
C5 N1 C1 121.31(12) . . ?
C5 N1 C4 126.94(12) . . ?
N1 C1 H1A 111.2 . . ?
N1 C1 H1B 111.2 . . ?
N1 C1 C2 102.69(12) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.2 . . ?
C2 C1 H1B 111.2 . . ?
C18 O2 H2 109.5 . . ?
C1 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C1 C2 C3 102.48(12) . . ?
H2A C2 H2B 109.2 . . ?
C3 C2 H2A 111.3 . . ?
C3 C2 H2B 111.3 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 C2 102.69(13) . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
N1 C4 C3 102.41(12) . . ?
N1 C4 H4A 111.3 . . ?
N1 C4 H4B 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
N1 C5 C6 118.55(12) . . ?
O3 C5 N1 121.23(13) . . ?
O3 C5 C6 120.17(12) . . ?
C7 C6 C5 119.69(12) . . ?
C7 C6 C11 119.84(12) . . ?
C11 C6 C5 120.21(12) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.95(14) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.46(13) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.07(13) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 121.06(13) . . ?
C11 C10 H10 119.5 . . ?
C6 C11 C12 123.36(11) . . ?
C10 C11 C6 118.61(12) . . ?
C10 C11 C12 117.98(12) . . ?
C13 C12 C11 119.74(12) . . ?
C17 C12 C11 120.38(11) . . ?
C17 C12 C13 119.48(12) . . ?
C12 C13 C18 122.25(13) . . ?
C14 C13 C12 120.49(14) . . ?
C14 C13 C18 117.26(13) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.05(14) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.73(14) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.2 . . ?
C15 C16 C17 121.59(14) . . ?
C17 C16 H16 119.2 . . ?
C12 C17 C19 121.92(11) . . ?
C16 C17 C12 118.60(13) . . ?
C16 C17 C19 119.47(13) . . ?
O1 C18 O2 120.94(15) . . ?
O1 C18 C13 121.90(15) . . ?
O2 C18 C13 117.08(13) . . ?
C17 C19 H19 107.7 . . ?
C17 C19 C20 111.43(14) . . ?
C17 C19 C21 111.08(13) . . ?
C20 C19 H19 107.7 . . ?
C21 C19 H19 107.7 . . ?
C21 C19 C20 111.15(14) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 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
N1 C1 C2 C3 33.87(15) . . . . ?
N1 C5 C6 C7 55.57(18) . . . . ?
N1 C5 C6 C11 -130.31(14) . . . . ?
C1 N1 C4 C3 -13.93(17) . . . . ?
C1 N1 C5 O3 2.9(2) . . . . ?
C1 N1 C5 C6 -174.42(12) . . . . ?
C1 C2 C3 C4 -43.14(16) . . . . ?
C2 C3 C4 N1 34.72(16) . . . . ?
O3 C5 C6 C7 -121.81(15) . . . . ?
O3 C5 C6 C11 52.30(18) . . . . ?
C4 N1 C1 C2 -12.60(16) . . . . ?
C4 N1 C5 O3 -170.85(14) . . . . ?
C4 N1 C5 C6 11.8(2) . . . . ?
C5 N1 C1 C2 172.74(13) . . . . ?
C5 N1 C4 C3 160.37(14) . . . . ?
C5 C6 C7 C8 173.37(13) . . . . ?
C5 C6 C11 C10 -173.93(12) . . . . ?
C5 C6 C11 C12 8.80(19) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C6 C11 C12 C13 -102.72(15) . . . . ?
C6 C11 C12 C17 84.56(16) . . . . ?
C7 C6 C11 C10 0.18(19) . . . . ?
C7 C6 C11 C12 -177.10(12) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 -1.4(2) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C9 C10 C11 C12 178.33(13) . . . . ?
C10 C11 C12 C13 79.99(16) . . . . ?
C10 C11 C12 C17 -92.73(15) . . . . ?
C11 C6 C7 C8 -0.8(2) . . . . ?
C11 C12 C13 C14 -169.95(12) . . . . ?
C11 C12 C13 C18 9.91(19) . . . . ?
C11 C12 C17 C16 171.43(12) . . . . ?
C11 C12 C17 C19 -7.77(18) . . . . ?
C12 C13 C14 C15 -2.2(2) . . . . ?
C12 C13 C18 O1 -129.74(17) . . . . ?
C12 C13 C18 O2 53.59(19) . . . . ?
C12 C17 C19 C20 -119.49(15) . . . . ?
C12 C17 C19 C21 115.99(15) . . . . ?
C13 C12 C17 C16 -1.31(18) . . . . ?
C13 C12 C17 C19 179.50(12) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C13 C18 O1 50.1(2) . . . . ?
C14 C13 C18 O2 -126.54(15) . . . . ?
C14 C15 C16 C17 1.6(2) . . . . ?
C15 C16 C17 C12 -0.9(2) . . . . ?
C15 C16 C17 C19 178.32(13) . . . . ?
C16 C17 C19 C20 61.32(18) . . . . ?
C16 C17 C19 C21 -63.20(18) . . . . ?
C17 C12 C13 C14 2.83(19) . . . . ?
C17 C12 C13 C18 -177.30(12) . . . . ?
C18 C13 C14 C15 177.97(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
