# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_AL001
_database_code_depnum_ccdc_archive 'CCDC 2237935'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H20 Cl N O2'
_chemical_formula_sum            'C19 H20 Cl N O2'
_chemical_formula_weight         329.81
_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'
Cl Cl 0.1484 0.1585 '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                   9.4108(6)
_cell_length_b                   7.4249(5)
_cell_length_c                   23.5740(16)
_cell_angle_alpha                90
_cell_angle_beta                 98.9610(10)
_cell_angle_gamma                90
_cell_volume                     1627.11(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6252
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.58
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.941
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.8673.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         1.749
_diffrn_ambient_temperature      120.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3111
_reflns_number_total             3551
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.9035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0802
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C10(H10), C17(H17), C18(H18), C9(H9), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_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
Cl1 Cl -0.04791(4) -0.02127(5) 0.66562(2) 0.02298(10) Uani 1 1 d . . . . .
O1 O 0.50878(10) 0.88960(13) 0.58897(4) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.66323(10) 0.71616(12) 0.65266(4) 0.0164(2) Uani 1 1 d . . . . .
N1 N 0.53283(12) 0.80719(15) 0.64796(5) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.30470(14) 0.72447(17) 0.59580(5) 0.0140(3) Uani 1 1 d . . . . .
C15 C 0.15324(15) 0.14004(18) 0.61243(6) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.1139 0.0727 0.5794 0.020 Uiso 1 1 calc R U . . .
C13 C 0.32920(14) 0.35493(17) 0.65877(6) 0.0147(3) Uani 1 1 d . . . . .
C14 C 0.26840(14) 0.25672(18) 0.61059(6) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.3064 0.2697 0.5758 0.019 Uiso 1 1 calc R U . . .
C1 C 0.37515(14) 0.83905(18) 0.56303(6) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.16469(15) 0.67129(18) 0.57538(6) 0.0166(3) Uani 1 1 d . . . . .
H10 H 0.1141 0.5950 0.5977 0.020 Uiso 1 1 calc R U . . .
C16 C 0.09711(14) 0.12378(18) 0.66306(6) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.15599(15) 0.21746(18) 0.71191(6) 0.0190(3) Uani 1 1 d . . . . .
H17 H 0.1171 0.2047 0.7465 0.023 Uiso 1 1 calc R U . . .
C18 C 0.27248(15) 0.33005(18) 0.70962(6) 0.0176(3) Uani 1 1 d . . . . .
H18 H 0.3147 0.3917 0.7434 0.021 Uiso 1 1 calc R U . . .
C4 C 0.45287(14) 0.48476(17) 0.65693(5) 0.0138(3) Uani 1 1 d . . . . .
H4 H 0.5197 0.4731 0.6941 0.017 Uiso 1 1 calc R U . . .
C9 C 0.09940(15) 0.73162(19) 0.52156(6) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.0035 0.6966 0.5071 0.022 Uiso 1 1 calc R U . . .
C3 C 0.40217(14) 0.68428(17) 0.65129(6) 0.0143(3) Uani 1 1 d . . . . .
C19 C 0.34131(15) 0.75195(18) 0.70378(6) 0.0180(3) Uani 1 1 d . . . . .
H19A H 0.4077 0.7212 0.7387 0.027 Uiso 1 1 calc R U . . .
H19B H 0.2478 0.6951 0.7050 0.027 Uiso 1 1 calc R U . . .
H19C H 0.3293 0.8830 0.7013 0.027 Uiso 1 1 calc R U . . .
C5 C 0.53976(14) 0.44533(18) 0.60854(6) 0.0163(3) Uani 1 1 d . . . . .
H5A H 0.5645 0.3157 0.6088 0.020 Uiso 1 1 calc R U . . .
H5B H 0.4808 0.4737 0.5711 0.020 Uiso 1 1 calc R U . . .
C8 C 0.17418(15) 0.84297(19) 0.48891(6) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.1289 0.8813 0.4520 0.023 Uiso 1 1 calc R U . . .
C7 C 0.31367(15) 0.89909(19) 0.50916(6) 0.0188(3) Uani 1 1 d . . . . .
H7 H 0.3647 0.9754 0.4870 0.023 Uiso 1 1 calc R U . . .
C6 C 0.67787(15) 0.55753(18) 0.61592(6) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.71753(17) 0.6181(2) 0.55861(6) 0.0236(3) Uani 1 1 d . . . . .
H12A H 0.6343 0.6763 0.5357 0.035 Uiso 1 1 calc R U . . .
H12B H 0.7462 0.5132 0.5378 0.035 Uiso 1 1 calc R U . . .
H12C H 0.7977 0.7037 0.5655 0.035 Uiso 1 1 calc R U . . .
C11 C 0.80321(16) 0.4577(2) 0.65086(7) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.8864 0.5384 0.6586 0.037 Uiso 1 1 calc R U . . .
H11B H 0.8282 0.3529 0.6292 0.037 Uiso 1 1 calc R U . . .
H11C H 0.7757 0.4177 0.6872 0.037 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
Cl1 C16 1.7470(14) . ?
O1 N1 1.5038(14) . ?
O1 C1 1.3627(16) . ?
O2 N1 1.3902(14) . ?
O2 C6 1.4811(16) . ?
N1 C3 1.5431(17) . ?
C2 C1 1.3855(18) . ?
C2 C10 1.3878(19) . ?
C2 C3 1.5060(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.3934(19) . ?
C15 C16 1.3836(19) . ?
C13 C14 1.3952(19) . ?
C13 C18 1.3984(19) . ?
C13 C4 1.5171(18) . ?
C14 H14 0.9500 . ?
C1 C7 1.3847(19) . ?
C10 H10 0.9500 . ?
C10 C9 1.3948(19) . ?
C16 C17 1.385(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C4 H4 1.0000 . ?
C4 C3 1.5557(18) . ?
C4 C5 1.5316(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.393(2) . ?
C3 C19 1.5271(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5307(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.389(2) . ?
C7 H7 0.9500 . ?
C6 C12 1.5245(19) . ?
C6 C11 1.5218(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 O1 N1 107.36(9) . . ?
N1 O2 C6 120.09(10) . . ?
O1 N1 C3 106.35(9) . . ?
O2 N1 O1 105.99(9) . . ?
O2 N1 C3 114.13(10) . . ?
C1 C2 C10 119.49(12) . . ?
C1 C2 C3 109.05(11) . . ?
C10 C2 C3 131.43(12) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C16 C15 C14 118.97(13) . . ?
C14 C13 C18 117.77(12) . . ?
C14 C13 C4 121.87(12) . . ?
C18 C13 C4 120.36(12) . . ?
C15 C14 C13 121.46(12) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O1 C1 C2 114.03(12) . . ?
O1 C1 C7 123.20(12) . . ?
C7 C1 C2 122.77(13) . . ?
C2 C10 H10 120.5 . . ?
C2 C10 C9 118.95(12) . . ?
C9 C10 H10 120.5 . . ?
C15 C16 Cl1 119.27(11) . . ?
C15 C16 C17 121.09(13) . . ?
C17 C16 Cl1 119.63(11) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.13(13) . . ?
C18 C17 H17 120.4 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.52(13) . . ?
C17 C18 H18 119.2 . . ?
C13 C4 H4 107.5 . . ?
C13 C4 C3 112.40(10) . . ?
C13 C4 C5 113.63(11) . . ?
C3 C4 H4 107.5 . . ?
C5 C4 H4 107.5 . . ?
C5 C4 C3 108.10(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.29(13) . . ?
C8 C9 H9 119.9 . . ?
N1 C3 C4 109.34(10) . . ?
C2 C3 N1 102.76(10) . . ?
C2 C3 C4 113.58(11) . . ?
C2 C3 C19 112.59(11) . . ?
C19 C3 N1 104.43(10) . . ?
C19 C3 C4 113.13(11) . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.71(11) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C9 C8 H8 119.3 . . ?
C7 C8 C9 121.33(13) . . ?
C7 C8 H8 119.3 . . ?
C1 C7 C8 117.14(13) . . ?
C1 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
O2 C6 C5 110.15(10) . . ?
O2 C6 C12 109.98(11) . . ?
O2 C6 C11 101.87(11) . . ?
C12 C6 C5 112.37(12) . . ?
C11 C6 C5 111.67(12) . . ?
C11 C6 C12 110.31(12) . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
Cl1 C16 C17 C18 179.00(10) . . . . ?
O1 N1 C3 C2 -6.61(12) . . . . ?
O1 N1 C3 C4 114.34(10) . . . . ?
O1 N1 C3 C19 -124.31(10) . . . . ?
O1 C1 C7 C8 -177.27(12) . . . . ?
O2 N1 C3 C2 -123.09(11) . . . . ?
O2 N1 C3 C4 -2.15(14) . . . . ?
O2 N1 C3 C19 119.20(11) . . . . ?
N1 O1 C1 C2 -2.65(14) . . . . ?
N1 O1 C1 C7 176.22(12) . . . . ?
N1 O2 C6 C5 -37.95(15) . . . . ?
N1 O2 C6 C12 86.44(14) . . . . ?
N1 O2 C6 C11 -156.58(11) . . . . ?
C2 C1 C7 C8 1.5(2) . . . . ?
C2 C10 C9 C8 0.2(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C13 C4 C3 N1 -178.39(10) . . . . ?
C13 C4 C3 C2 -64.27(14) . . . . ?
C13 C4 C3 C19 65.69(14) . . . . ?
C13 C4 C5 C6 -169.44(11) . . . . ?
C14 C15 C16 Cl1 179.65(10) . . . . ?
C14 C15 C16 C17 -1.8(2) . . . . ?
C14 C13 C18 C17 -2.6(2) . . . . ?
C14 C13 C4 C3 100.69(14) . . . . ?
C14 C13 C4 C5 -22.48(17) . . . . ?
C1 O1 N1 O2 127.71(10) . . . . ?
C1 O1 N1 C3 5.89(12) . . . . ?
C1 C2 C10 C9 1.45(19) . . . . ?
C1 C2 C3 N1 5.27(13) . . . . ?
C1 C2 C3 C4 -112.72(12) . . . . ?
C1 C2 C3 C19 117.05(12) . . . . ?
C10 C2 C1 O1 176.50(11) . . . . ?
C10 C2 C1 C7 -2.4(2) . . . . ?
C10 C2 C3 N1 -172.81(13) . . . . ?
C10 C2 C3 C4 69.20(18) . . . . ?
C10 C2 C3 C19 -61.03(18) . . . . ?
C10 C9 C8 C7 -1.1(2) . . . . ?
C16 C15 C14 C13 0.9(2) . . . . ?
C16 C17 C18 C13 1.8(2) . . . . ?
C18 C13 C14 C15 1.19(19) . . . . ?
C18 C13 C4 C3 -79.41(15) . . . . ?
C18 C13 C4 C5 157.42(12) . . . . ?
C4 C13 C14 C15 -178.91(12) . . . . ?
C4 C13 C18 C17 177.52(12) . . . . ?
C4 C5 C6 O2 -21.23(15) . . . . ?
C4 C5 C6 C12 -144.23(12) . . . . ?
C4 C5 C6 C11 91.20(13) . . . . ?
C9 C8 C7 C1 0.2(2) . . . . ?
C3 C2 C1 O1 -1.84(15) . . . . ?
C3 C2 C1 C7 179.28(12) . . . . ?
C3 C2 C10 C9 179.36(13) . . . . ?
C3 C4 C5 C6 65.07(14) . . . . ?
C5 C4 C3 N1 -52.18(13) . . . . ?
C5 C4 C3 C2 61.94(14) . . . . ?
C5 C4 C3 C19 -168.10(11) . . . . ?
C6 O2 N1 O1 -65.80(12) . . . . ?
C6 O2 N1 C3 50.90(14) . . . . ?

_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_AL261
_database_code_depnum_ccdc_archive 'CCDC 2237936'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H25 N O7'
_chemical_formula_sum            'C23 H25 N O7'
_chemical_formula_weight         427.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           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                   8.2690(2)
_cell_length_b                   11.3776(3)
_cell_length_c                   12.6210(3)
_cell_angle_alpha                65.3470(10)
_cell_angle_beta                 81.305(2)
_cell_angle_gamma                82.114(2)
_cell_volume                     1063.13(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6357
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.50
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0801 before and 0.0396 after correction.
The Ratio of minimum to maximum transmission is 0.8880.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10765
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         1.785
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3809
_reflns_number_total             4440
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4440
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0295P)²+0.6189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0981
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
;
_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 -0.49395(13) -0.14443(10) -0.91117(8) 0.0196(2) Uani 1 1 d . . . . .
O2 O -0.63352(12) -0.32573(10) -0.85306(8) 0.0166(2) Uani 1 1 d . . . . .
O3 O -0.77050(14) -0.62591(11) -0.64073(9) 0.0236(2) Uani 1 1 d . . . . .
O4 O -0.78795(12) -0.51376(10) -0.83427(8) 0.0180(2) Uani 1 1 d . . . . .
O5 O -0.72420(13) -0.42060(11) -0.54624(9) 0.0210(2) Uani 1 1 d . . . . .
O6 O -0.86455(12) -0.28861(11) -0.69851(9) 0.0225(2) Uani 1 1 d . . . . .
O7 O -0.14936(13) -0.88865(10) -0.81875(9) 0.0211(2) Uani 1 1 d . . . . .
N1 N -0.46718(14) -0.28060(12) -0.88736(10) 0.0162(3) Uani 1 1 d . . . . .
C1 C -0.48660(17) -0.13198(14) -0.80715(12) 0.0169(3) Uani 1 1 d . . . . .
C2 C -0.42788(16) -0.24610(14) -0.72176(12) 0.0148(3) Uani 1 1 d . . . . .
C3 C -0.38421(16) -0.34392(14) -0.77535(12) 0.0149(3) Uani 1 1 d . . . . .
C4 C -0.46576(16) -0.47246(14) -0.70837(11) 0.0141(3) Uani 1 1 d . . . . .
H4 H -0.4620 -0.5003 -0.6224 0.017 Uiso 1 1 calc R U . . .
C5 C -0.64419(16) -0.42552(14) -0.73762(11) 0.0143(3) Uani 1 1 d . . . . .
C6 C -0.52472(18) -0.01794(15) -0.79196(13) 0.0202(3) Uani 1 1 d . . . . .
H6 H -0.5655 0.0594 -0.8520 0.024 Uiso 1 1 calc R U . . .
C7 C -0.50007(18) -0.02256(15) -0.68363(13) 0.0210(3) Uani 1 1 d . . . . .
H7 H -0.5241 0.0539 -0.6692 0.025 Uiso 1 1 calc R U . . .
C8 C -0.44104(18) -0.13635(15) -0.59582(13) 0.0191(3) Uani 1 1 d . . . . .
H8 H -0.4256 -0.1364 -0.5227 0.023 Uiso 1 1 calc R U . . .
C9 C -0.40444(17) -0.24988(15) -0.61400(12) 0.0168(3) Uani 1 1 d . . . . .
H9 H -0.3645 -0.3279 -0.5542 0.020 Uiso 1 1 calc R U . . .
C10 C -0.74020(16) -0.53494(14) -0.73172(12) 0.0146(3) Uani 1 1 d . . . . .
C11 C -0.88813(18) -0.61065(15) -0.83374(14) 0.0215(3) Uani 1 1 d . . . . .
H11A H -0.9519 -0.5716 -0.9024 0.026 Uiso 1 1 calc R U . . .
H11B H -0.9669 -0.6370 -0.7621 0.026 Uiso 1 1 calc R U . . .
C12 C -0.7848(2) -0.72829(16) -0.83736(15) 0.0251(3) Uani 1 1 d . . . . .
H12A H -0.7277 -0.7709 -0.7665 0.038 Uiso 1 1 calc R U . . .
H12B H -0.7040 -0.7022 -0.9067 0.038 Uiso 1 1 calc R U . . .
H12C H -0.8552 -0.7887 -0.8413 0.038 Uiso 1 1 calc R U . . .
C13 C -0.74595(16) -0.37675(14) -0.64794(12) 0.0159(3) Uani 1 1 d . . . . .
C14 C -0.97937(19) -0.24065(19) -0.62205(16) 0.0294(4) Uani 1 1 d . . . . .
H14A H -0.9944 -0.3113 -0.5429 0.035 Uiso 1 1 calc R U . . .
H14B H -1.0874 -0.2142 -0.6535 0.035 Uiso 1 1 calc R U . . .
C15 C -0.9179(2) -0.12763(17) -0.61334(15) 0.0283(4) Uani 1 1 d . . . . .
H15A H -0.9965 -0.0981 -0.5614 0.043 Uiso 1 1 calc R U . . .
H15B H -0.9054 -0.0568 -0.6914 0.043 Uiso 1 1 calc R U . . .
H15C H -0.8114 -0.1539 -0.5815 0.043 Uiso 1 1 calc R U . . .
C16 C -0.38906(16) -0.58139(14) -0.74262(12) 0.0143(3) Uani 1 1 d . . . . .
C17 C -0.38467(17) -0.57711(14) -0.85507(12) 0.0172(3) Uani 1 1 d . . . . .
H17 H -0.4359 -0.5035 -0.9132 0.021 Uiso 1 1 calc R U . . .
C18 C -0.30735(17) -0.67755(14) -0.88454(12) 0.0161(3) Uani 1 1 d . . . . .
H18 H -0.3061 -0.6726 -0.9617 0.019 Uiso 1 1 calc R U . . .
C19 C -0.23186(16) -0.78520(14) -0.79988(12) 0.0156(3) Uani 1 1 d . . . . .
C20 C -0.23606(17) -0.79197(14) -0.68668(12) 0.0181(3) Uani 1 1 d . . . . .
H20 H -0.1859 -0.8660 -0.6284 0.022 Uiso 1 1 calc R U . . .
C21 C -0.31288(17) -0.69139(14) -0.65935(12) 0.0158(3) Uani 1 1 d . . . . .
H21 H -0.3141 -0.6969 -0.5820 0.019 Uiso 1 1 calc R U . . .
C22 C -0.1440(2) -0.88687(17) -0.93278(14) 0.0277(4) Uani 1 1 d . . . . .
H22A H -0.0819 -0.9658 -0.9349 0.042 Uiso 1 1 calc R U . . .
H22B H -0.0904 -0.8107 -0.9906 0.042 Uiso 1 1 calc R U . . .
H22C H -0.2560 -0.8829 -0.9513 0.042 Uiso 1 1 calc R U . . .
C23 C -0.19900(17) -0.35780(16) -0.80715(14) 0.0215(3) Uani 1 1 d . . . . .
H23A H -0.1585 -0.2715 -0.8498 0.032 Uiso 1 1 calc R U . . .
H23B H -0.1750 -0.4067 -0.8566 0.032 Uiso 1 1 calc R U . . .
H23C H -0.1446 -0.4041 -0.7354 0.032 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 N1 1.4412(15) . ?
O1 C1 1.3888(17) . ?
O2 N1 1.4735(15) . ?
O2 C5 1.4242(16) . ?
O3 C10 1.2022(17) . ?
O4 C10 1.3256(16) . ?
O4 C11 1.4643(17) . ?
O5 C13 1.1999(17) . ?
O6 C13 1.3267(17) . ?
O6 C14 1.4665(18) . ?
O7 C19 1.3681(17) . ?
O7 C22 1.4249(18) . ?
N1 C3 1.5153(17) . ?
C1 C2 1.379(2) . ?
C1 C6 1.377(2) . ?
C2 C3 1.5068(19) . ?
C2 C9 1.3848(19) . ?
C3 C4 1.5412(19) . ?
C3 C23 1.5271(19) . ?
C4 H4 1.0000 . ?
C4 C5 1.5435(18) . ?
C4 C16 1.5078(19) . ?
C5 C10 1.5368(19) . ?
C5 C13 1.5507(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.500(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.496(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3947(19) . ?
C16 C21 1.3979(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.391(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.390(2) . ?
C19 C20 1.394(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.377(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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 O1 N1 107.56(10) . . ?
C5 O2 N1 110.35(9) . . ?
C10 O4 C11 115.73(11) . . ?
C13 O6 C14 116.41(12) . . ?
C19 O7 C22 117.45(12) . . ?
O1 N1 O2 103.78(9) . . ?
O1 N1 C3 105.94(10) . . ?
O2 N1 C3 104.42(9) . . ?
C2 C1 O1 112.03(13) . . ?
C6 C1 O1 124.45(13) . . ?
C6 C1 C2 123.43(13) . . ?
C1 C2 C3 107.59(12) . . ?
C1 C2 C9 119.98(14) . . ?
C9 C2 C3 132.08(13) . . ?
N1 C3 C4 103.42(10) . . ?
N1 C3 C23 108.76(11) . . ?
C2 C3 N1 102.47(11) . . ?
C2 C3 C4 114.91(11) . . ?
C2 C3 C23 110.64(12) . . ?
C23 C3 C4 115.35(12) . . ?
C3 C4 H4 109.0 . . ?
C3 C4 C5 99.95(11) . . ?
C5 C4 H4 109.0 . . ?
C16 C4 C3 114.36(11) . . ?
C16 C4 H4 109.0 . . ?
C16 C4 C5 115.04(11) . . ?
O2 C5 C4 106.15(10) . . ?
O2 C5 C10 110.40(11) . . ?
O2 C5 C13 111.75(11) . . ?
C4 C5 C13 112.28(11) . . ?
C10 C5 C4 112.53(11) . . ?
C10 C5 C13 103.86(11) . . ?
C1 C6 H6 121.9 . . ?
C1 C6 C7 116.16(14) . . ?
C7 C6 H6 121.9 . . ?
C6 C7 H7 119.2 . . ?
C6 C7 C8 121.65(14) . . ?
C8 C7 H7 119.2 . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.66(13) . . ?
C9 C8 H8 119.7 . . ?
C2 C9 C8 118.11(13) . . ?
C2 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
O3 C10 O4 125.89(13) . . ?
O3 C10 C5 121.28(12) . . ?
O4 C10 C5 112.78(11) . . ?
O4 C11 H11A 109.3 . . ?
O4 C11 H11B 109.3 . . ?
O4 C11 C12 111.76(12) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 126.27(13) . . ?
O5 C13 C5 123.43(13) . . ?
O6 C13 C5 110.13(11) . . ?
O6 C14 H14A 109.4 . . ?
O6 C14 H14B 109.4 . . ?
O6 C14 C15 111.29(13) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C4 123.50(12) . . ?
C17 C16 C21 117.45(13) . . ?
C21 C16 C4 119.01(12) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.85(13) . . ?
C18 C17 H17 119.1 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.26(13) . . ?
C19 C18 H18 120.4 . . ?
O7 C19 C18 124.69(12) . . ?
O7 C19 C20 115.48(12) . . ?
C18 C19 C20 119.83(13) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.01(13) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.60(13) . . ?
C20 C21 H21 119.2 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C23 H23A 109.5 . . ?
C3 C23 H23B 109.5 . . ?
C3 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 N1 C3 C2 20.44(12) . . . . ?
O1 N1 C3 C4 140.20(10) . . . . ?
O1 N1 C3 C23 -96.71(12) . . . . ?
O1 C1 C2 C3 2.69(16) . . . . ?
O1 C1 C2 C9 176.76(12) . . . . ?
O1 C1 C6 C7 -176.07(13) . . . . ?
O2 N1 C3 C2 -88.78(11) . . . . ?
O2 N1 C3 C4 30.97(13) . . . . ?
O2 N1 C3 C23 154.06(11) . . . . ?
O2 C5 C10 O3 -176.30(13) . . . . ?
O2 C5 C10 O4 1.32(16) . . . . ?
O2 C5 C13 O5 -151.24(13) . . . . ?
O2 C5 C13 O6 33.25(15) . . . . ?
O7 C19 C20 C21 178.54(13) . . . . ?
N1 O1 C1 C2 10.99(15) . . . . ?
N1 O1 C1 C6 -172.28(13) . . . . ?
N1 O2 C5 C4 -15.47(14) . . . . ?
N1 O2 C5 C10 -137.70(11) . . . . ?
N1 O2 C5 C13 107.24(12) . . . . ?
N1 C3 C4 C5 -38.88(12) . . . . ?
N1 C3 C4 C16 84.57(13) . . . . ?
C1 O1 N1 O2 89.90(11) . . . . ?
C1 O1 N1 C3 -19.78(13) . . . . ?
C1 C2 C3 N1 -14.28(14) . . . . ?
C1 C2 C3 C4 -125.68(12) . . . . ?
C1 C2 C3 C23 101.51(13) . . . . ?
C1 C2 C9 C8 -0.3(2) . . . . ?
C1 C6 C7 C8 -0.3(2) . . . . ?
C2 C1 C6 C7 0.3(2) . . . . ?
C2 C3 C4 C5 71.95(13) . . . . ?
C2 C3 C4 C16 -164.60(11) . . . . ?
C3 C2 C9 C8 172.11(14) . . . . ?
C3 C4 C5 O2 33.54(13) . . . . ?
C3 C4 C5 C10 154.40(11) . . . . ?
C3 C4 C5 C13 -88.84(12) . . . . ?
C3 C4 C16 C17 -62.08(17) . . . . ?
C3 C4 C16 C21 115.66(14) . . . . ?
C4 C5 C10 O3 65.30(17) . . . . ?
C4 C5 C10 O4 -117.07(12) . . . . ?
C4 C5 C13 O5 -32.10(18) . . . . ?
C4 C5 C13 O6 152.39(12) . . . . ?
C4 C16 C17 C18 177.54(13) . . . . ?
C4 C16 C21 C20 -177.81(13) . . . . ?
C5 O2 N1 O1 -120.63(11) . . . . ?
C5 O2 N1 C3 -9.84(13) . . . . ?
C5 C4 C16 C17 52.81(18) . . . . ?
C5 C4 C16 C21 -129.44(13) . . . . ?
C6 C1 C2 C3 -174.07(13) . . . . ?
C6 C1 C2 C9 0.0(2) . . . . ?
C6 C7 C8 C9 0.1(2) . . . . ?
C7 C8 C9 C2 0.2(2) . . . . ?
C9 C2 C3 N1 172.65(14) . . . . ?
C9 C2 C3 C4 61.25(19) . . . . ?
C9 C2 C3 C23 -71.55(19) . . . . ?
C10 O4 C11 C12 -80.79(16) . . . . ?
C10 C5 C13 O5 89.74(15) . . . . ?
C10 C5 C13 O6 -85.76(13) . . . . ?
C11 O4 C10 O3 0.8(2) . . . . ?
C11 O4 C10 C5 -176.70(11) . . . . ?
C13 O6 C14 C15 87.76(17) . . . . ?
C13 C5 C10 O3 -56.37(17) . . . . ?
C13 C5 C10 O4 121.26(12) . . . . ?
C14 O6 C13 O5 0.1(2) . . . . ?
C14 O6 C13 C5 175.43(12) . . . . ?
C16 C4 C5 O2 -89.44(13) . . . . ?
C16 C4 C5 C10 31.43(16) . . . . ?
C16 C4 C5 C13 148.19(12) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C17 C16 C21 C20 0.1(2) . . . . ?
C17 C18 C19 O7 -178.65(13) . . . . ?
C17 C18 C19 C20 0.7(2) . . . . ?
C18 C19 C20 C21 -0.9(2) . . . . ?
C19 C20 C21 C16 0.5(2) . . . . ?
C21 C16 C17 C18 -0.2(2) . . . . ?
C22 O7 C19 C18 -1.5(2) . . . . ?
C22 O7 C19 C20 179.07(13) . . . . ?
C23 C3 C4 C5 -157.49(11) . . . . ?
C23 C3 C4 C16 -34.04(16) . . . . ?

_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_al302_305
_database_code_depnum_ccdc_archive 'CCDC 2250121'
loop_
_audit_author_name
_audit_author_address
'Svetlana Aksenova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N O6'
_chemical_formula_sum            'C19 H25 N O6'
_chemical_formula_weight         363.40
_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                   7.6481(4)
_cell_length_b                   14.5397(9)
_cell_length_c                   16.0367(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.315(2)
_cell_angle_gamma                90
_cell_volume                     1768.78(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2511
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.63
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0950 before and 0.0474 after correction.
The Ratio of minimum to maximum transmission is 0.8469.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_av_unetI/netI     0.0604
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11391
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.898
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3145
_reflns_number_total             4500
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.338
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0511
_refine_ls_restrained_S_all      1.033
_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)+(0.0346P)²+0.7016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O2(H2)
2.b Ternary CH refined with riding coordinates:
 C12(H12), C1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C8(H8A,H8B), C10(H10A,H10B), C9(H9A,H9B), C18(H18A,H18B),
 C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C5(H5)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O6 O 0.42524(15) 0.73890(9) 0.54659(8) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.77749(15) 0.67216(9) 0.43512(8) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.8660 0.7028 0.4625 0.022 Uiso 1 1 d R U . . .
O4 O 0.46945(15) 0.58661(9) 0.40845(8) 0.0211(3) Uani 1 1 d . . . . .
O5 O 0.69710(16) 0.68504(9) 0.59413(8) 0.0210(3) Uani 1 1 d . . . . .
O1 O 1.02154(16) 0.85570(10) 0.58189(8) 0.0226(3) Uani 1 1 d . . . . .
O3 O 0.35965(16) 0.71676(9) 0.34572(8) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.94494(18) 0.83251(11) 0.49427(9) 0.0165(3) Uani 1 1 d . . . . .
C17 C 0.4687(2) 0.67686(12) 0.39293(11) 0.0171(4) Uani 1 1 d . . . . .
C12 C 0.6393(2) 0.82495(12) 0.41959(11) 0.0152(3) Uani 1 1 d . . . . .
H12 H 0.5207 0.8533 0.4213 0.018 Uiso 1 1 calc R U . . .
C2 C 0.7306(2) 0.89851(12) 0.56748(11) 0.0171(4) Uani 1 1 d . . . . .
C1 C 0.7713(2) 0.88127(12) 0.47922(11) 0.0154(4) Uani 1 1 d . . . . .
H1 H 0.7896 0.9419 0.4522 0.019 Uiso 1 1 calc R U . . .
C13 C 0.6255(2) 0.72318(12) 0.44685(11) 0.0154(4) Uani 1 1 d . . . . .
C11 C 0.6786(2) 0.83040(13) 0.32669(11) 0.0176(4) Uani 1 1 d . . . . .
H11A H 0.6874 0.7667 0.3058 0.021 Uiso 1 1 calc R U . . .
H11B H 0.5753 0.8591 0.2930 0.021 Uiso 1 1 calc R U . . .
C7 C 0.8822(2) 0.88253(13) 0.62192(12) 0.0199(4) Uani 1 1 d . . . . .
C3 C 0.5817(2) 0.93076(13) 0.59829(12) 0.0214(4) Uani 1 1 d . . . . .
H3 H 0.4770 0.9431 0.5615 0.026 Uiso 1 1 calc R U . . .
C14 C 0.5906(2) 0.71318(12) 0.53879(11) 0.0174(4) Uani 1 1 d . . . . .
C8 C 1.0724(2) 0.86875(13) 0.44149(11) 0.0200(4) Uani 1 1 d . . . . .
H8A H 1.1907 0.8432 0.4607 0.024 Uiso 1 1 calc R U . . .
H8B H 1.0791 0.9365 0.4473 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8437(2) 0.88266(13) 0.30820(11) 0.0198(4) Uani 1 1 d . . . . .
H10A H 0.8454 0.8836 0.2466 0.024 Uiso 1 1 calc R U . . .
H10B H 0.8339 0.9472 0.3269 0.024 Uiso 1 1 calc R U . . .
C9 C 1.0193(2) 0.84372(14) 0.34956(12) 0.0227(4) Uani 1 1 d . . . . .
H9A H 1.0142 0.7758 0.3450 0.027 Uiso 1 1 calc R U . . .
H9B H 1.1133 0.8651 0.3171 0.027 Uiso 1 1 calc R U . . .
C18 C 0.3204(2) 0.53422(13) 0.36669(13) 0.0229(4) Uani 1 1 d . . . . .
H18A H 0.3579 0.4702 0.3576 0.027 Uiso 1 1 calc R U . . .
H18B H 0.2807 0.5618 0.3111 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5883(3) 0.94481(14) 0.68473(13) 0.0271(5) Uani 1 1 d . . . . .
H4 H 0.4874 0.9675 0.7070 0.033 Uiso 1 1 calc R U . . .
C15 C 0.3703(2) 0.73304(15) 0.63038(12) 0.0247(4) Uani 1 1 d . . . . .
H15A H 0.3065 0.7898 0.6424 0.030 Uiso 1 1 calc R U . . .
H15B H 0.4753 0.7273 0.6730 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8915(3) 0.89378(14) 0.70784(12) 0.0255(4) Uani 1 1 d . . . . .
H6 H 0.9960 0.8802 0.7444 0.031 Uiso 1 1 calc R U . . .
C5 C 0.7410(3) 0.92587(14) 0.73824(13) 0.0281(5) Uani 1 1 d . . . . .
H5 H 0.7426 0.9351 0.7970 0.034 Uiso 1 1 calc R U . . .
C19 C 0.1700(2) 0.53378(15) 0.41881(13) 0.0288(5) Uani 1 1 d . . . . .
H19A H 0.0721 0.4976 0.3901 0.043 Uiso 1 1 calc R U . . .
H19B H 0.1306 0.5970 0.4264 0.043 Uiso 1 1 calc R U . . .
H19C H 0.2092 0.5064 0.4738 0.043 Uiso 1 1 calc R U . . .
C16 C 0.2528(3) 0.65142(17) 0.63505(14) 0.0387(6) Uani 1 1 d . . . . .
H16A H 0.1480 0.6579 0.5934 0.058 Uiso 1 1 calc R U . . .
H16B H 0.2169 0.6475 0.6915 0.058 Uiso 1 1 calc R U . . .
H16C H 0.3165 0.5954 0.6233 0.058 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
O6 C14 1.340(2) . ?
O6 C15 1.461(2) . ?
O2 H2 0.8796 . ?
O2 C13 1.4119(19) . ?
O4 C17 1.335(2) . ?
O4 C18 1.461(2) . ?
O5 C14 1.198(2) . ?
O1 N1 1.4906(19) . ?
O1 C7 1.369(2) . ?
O3 C17 1.202(2) . ?
N1 C1 1.498(2) . ?
N1 C8 1.468(2) . ?
C17 C13 1.541(2) . ?
C12 H12 1.0000 . ?
C12 C1 1.536(2) . ?
C12 C13 1.550(2) . ?
C12 C11 1.559(2) . ?
C2 C1 1.508(2) . ?
C2 C7 1.380(2) . ?
C2 C3 1.380(2) . ?
C1 H1 1.0000 . ?
C13 C14 1.538(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C10 1.534(2) . ?
C7 C6 1.380(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.396(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C9 1.529(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.506(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.496(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.387(3) . ?
C5 H5 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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
C14 O6 C15 117.08(14) . . ?
C13 O2 H2 105.2 . . ?
C17 O4 C18 116.25(14) . . ?
C7 O1 N1 105.70(12) . . ?
O1 N1 C1 106.19(12) . . ?
C8 N1 O1 104.61(12) . . ?
C8 N1 C1 112.18(14) . . ?
O4 C17 C13 109.89(14) . . ?
O3 C17 O4 125.31(16) . . ?
O3 C17 C13 124.77(16) . . ?
C1 C12 H12 106.9 . . ?
C1 C12 C13 113.36(14) . . ?
C1 C12 C11 112.13(14) . . ?
C13 C12 H12 106.9 . . ?
C13 C12 C11 110.26(14) . . ?
C11 C12 H12 106.9 . . ?
C7 C2 C1 107.95(15) . . ?
C3 C2 C1 132.15(17) . . ?
C3 C2 C7 119.75(17) . . ?
N1 C1 C12 110.31(14) . . ?
N1 C1 C2 102.26(13) . . ?
N1 C1 H1 108.5 . . ?
C12 C1 H1 108.5 . . ?
C2 C1 C12 118.36(14) . . ?
C2 C1 H1 108.5 . . ?
O2 C13 C17 106.91(14) . . ?
O2 C13 C12 112.14(13) . . ?
O2 C13 C14 108.91(13) . . ?
C17 C13 C12 109.59(14) . . ?
C14 C13 C17 106.21(13) . . ?
C14 C13 C12 112.75(14) . . ?
C12 C11 H11A 107.8 . . ?
C12 C11 H11B 107.8 . . ?
H11A C11 H11B 107.1 . . ?
C10 C11 C12 118.24(15) . . ?
C10 C11 H11A 107.8 . . ?
C10 C11 H11B 107.8 . . ?
O1 C7 C2 113.15(15) . . ?
O1 C7 C6 123.91(17) . . ?
C2 C7 C6 122.94(17) . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.59(18) . . ?
C4 C3 H3 120.7 . . ?
O6 C14 C13 110.12(14) . . ?
O5 C14 O6 125.95(17) . . ?
O5 C14 C13 123.93(16) . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
N1 C8 C9 110.96(14) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C9 C10 C11 115.59(15) . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
C8 C9 C10 116.28(15) . . ?
C8 C9 H9A 108.2 . . ?
C8 C9 H9B 108.2 . . ?
C10 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
O4 C18 C19 110.77(16) . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.46(18) . . ?
C5 C4 H4 119.8 . . ?
O6 C15 H15A 109.7 . . ?
O6 C15 H15B 109.7 . . ?
O6 C15 C16 109.71(17) . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C7 C6 H6 121.6 . . ?
C7 C6 C5 116.84(18) . . ?
C5 C6 H6 121.6 . . ?
C4 C5 C6 121.38(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
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 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C13 C14 O6 -163.29(14) . . . . ?
O2 C13 C14 O5 15.7(2) . . . . ?
O4 C17 C13 O2 50.30(18) . . . . ?
O4 C17 C13 C12 172.06(14) . . . . ?
O4 C17 C13 C14 -65.88(17) . . . . ?
O1 N1 C1 C12 -147.45(13) . . . . ?
O1 N1 C1 C2 -20.68(16) . . . . ?
O1 N1 C8 C9 175.60(14) . . . . ?
O1 C7 C6 C5 176.79(18) . . . . ?
O3 C17 C13 O2 -131.51(18) . . . . ?
O3 C17 C13 C12 -9.8(2) . . . . ?
O3 C17 C13 C14 112.31(19) . . . . ?
N1 O1 C7 C2 -13.0(2) . . . . ?
N1 O1 C7 C6 167.78(17) . . . . ?
N1 C8 C9 C10 62.5(2) . . . . ?
C17 O4 C18 C19 -87.6(2) . . . . ?
C17 C13 C14 O6 -48.46(18) . . . . ?
C17 C13 C14 O5 130.53(18) . . . . ?
C12 C13 C14 O6 71.57(18) . . . . ?
C12 C13 C14 O5 -109.44(19) . . . . ?
C12 C11 C10 C9 62.1(2) . . . . ?
C2 C7 C6 C5 -2.4(3) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C1 N1 C8 C9 -69.73(19) . . . . ?
C1 C12 C13 O2 -71.23(18) . . . . ?
C1 C12 C13 C17 170.21(13) . . . . ?
C1 C12 C13 C14 52.14(18) . . . . ?
C1 C12 C11 C10 4.3(2) . . . . ?
C1 C2 C7 O1 -0.5(2) . . . . ?
C1 C2 C7 C6 178.74(17) . . . . ?
C1 C2 C3 C4 -176.04(18) . . . . ?
C13 C12 C1 N1 50.83(18) . . . . ?
C13 C12 C1 C2 -66.36(19) . . . . ?
C13 C12 C11 C10 -123.05(16) . . . . ?
C11 C12 C1 N1 -74.82(17) . . . . ?
C11 C12 C1 C2 167.98(15) . . . . ?
C11 C12 C13 O2 55.42(18) . . . . ?
C11 C12 C13 C17 -63.15(17) . . . . ?
C11 C12 C13 C14 178.79(13) . . . . ?
C11 C10 C9 C8 -80.4(2) . . . . ?
C7 O1 N1 C1 21.18(17) . . . . ?
C7 O1 N1 C8 140.00(14) . . . . ?
C7 C2 C1 N1 13.51(18) . . . . ?
C7 C2 C1 C12 134.90(16) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C6 C5 C4 0.6(3) . . . . ?
C3 C2 C1 N1 -171.16(19) . . . . ?
C3 C2 C1 C12 -49.8(3) . . . . ?
C3 C2 C7 O1 -176.54(16) . . . . ?
C3 C2 C7 C6 2.7(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C14 O6 C15 C16 -104.49(19) . . . . ?
C8 N1 C1 C12 98.84(16) . . . . ?
C8 N1 C1 C2 -134.38(15) . . . . ?
C18 O4 C17 O3 -2.8(3) . . . . ?
C18 O4 C17 C13 175.41(14) . . . . ?
C15 O6 C14 O5 0.7(3) . . . . ?
C15 O6 C14 C13 179.67(15) . . . . ?

_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_al367_211
_database_code_depnum_ccdc_archive 'CCDC 2250122'
loop_
_audit_author_name
_audit_author_address
'Svetlana Aksenova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H25 N O4'
_chemical_formula_sum            'C21 H25 N O4'
_chemical_formula_weight         355.42
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   16.0364(3)
_cell_length_b                   7.7955(2)
_cell_length_c                   29.9446(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.0650(10)
_cell_angle_gamma                90
_cell_volume                     3631.20(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6544
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0811 before and 0.0470 after correction.
The Ratio of minimum to maximum transmission is 0.8989.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0314
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            17677
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         2.619
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4044
_reflns_number_total             4806
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0408
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+3.2761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0973
_refine_ls_wR_factor_ref         0.1050
_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:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C21(H21), C20(H20), C16(H16), C17(H17), C6(H6), C4(H4), C5(H5)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C3(H3A,H3B,H3C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32983(5) 0.14522(11) 0.56701(3) 0.01570(18) Uani 1 1 d . . . . .
O2 O 0.33592(5) 0.41782(10) 0.59069(3) 0.01453(17) Uani 1 1 d . . . . .
O3 O 0.59460(5) 0.32954(11) 0.54933(3) 0.01651(18) Uani 1 1 d . . . . .
O4 O 0.85326(5) 0.42590(12) 0.72789(3) 0.02016(19) Uani 1 1 d . . . . .
N1 N 0.36876(6) 0.24731(12) 0.60611(3) 0.01356(19) Uani 1 1 d . . . . .
C1 C 0.45884(7) 0.23623(14) 0.55531(4) 0.0123(2) Uani 1 1 d . . . . .
C21 C 0.65610(7) 0.50684(14) 0.64154(4) 0.0137(2) Uani 1 1 d . . . . .
H21 H 0.6397 0.5658 0.6130 0.016 Uiso 1 1 calc R U . . .
C7 C 0.37889(7) 0.16894(14) 0.53487(4) 0.0140(2) Uani 1 1 d . . . . .
C15 C 0.59343(7) 0.41962(14) 0.65806(4) 0.0129(2) Uani 1 1 d . . . . .
C2 C 0.51612(7) 0.26552(14) 0.52789(4) 0.0136(2) Uani 1 1 d . . . . .
C10 C 0.50003(7) 0.42430(14) 0.63077(4) 0.0124(2) Uani 1 1 d . . . . .
H10 H 0.4960 0.5125 0.6061 0.015 Uiso 1 1 calc R U . . .
C20 C 0.74149(7) 0.50934(15) 0.66579(4) 0.0151(2) Uani 1 1 d . . . . .
H20 H 0.7828 0.5703 0.6540 0.018 Uiso 1 1 calc R U . . .
C8 C 0.46370(7) 0.25303(14) 0.60633(4) 0.0119(2) Uani 1 1 d . . . . .
C16 C 0.61986(7) 0.33885(15) 0.70072(4) 0.0148(2) Uani 1 1 d . . . . .
H16 H 0.5782 0.2828 0.7133 0.018 Uiso 1 1 calc R U . . .
C18 C 0.76663(7) 0.42236(15) 0.70750(4) 0.0151(2) Uani 1 1 d . . . . .
C9 C 0.50210(7) 0.09031(15) 0.63153(4) 0.0158(2) Uani 1 1 d . . . . .
H9A H 0.4938 0.0915 0.6629 0.024 Uiso 1 1 calc R U . . .
H9B H 0.5637 0.0854 0.6328 0.024 Uiso 1 1 calc R U . . .
H9C H 0.4734 -0.0104 0.6151 0.024 Uiso 1 1 calc R U . . .
C12 C 0.35071(7) 0.52599(15) 0.63132(4) 0.0142(2) Uani 1 1 d . . . . .
C17 C 0.70566(7) 0.33789(15) 0.72543(4) 0.0152(2) Uani 1 1 d . . . . .
H17 H 0.7222 0.2802 0.7542 0.018 Uiso 1 1 calc R U . . .
C6 C 0.35056(8) 0.12777(15) 0.48902(4) 0.0169(2) Uani 1 1 d . . . . .
H6 H 0.2950 0.0815 0.4764 0.020 Uiso 1 1 calc R U . . .
C11 C 0.44075(7) 0.48408(15) 0.66118(4) 0.0150(2) Uani 1 1 d . . . . .
H11A H 0.4364 0.3927 0.6835 0.018 Uiso 1 1 calc R U . . .
H11B H 0.4655 0.5872 0.6788 0.018 Uiso 1 1 calc R U . . .
C4 C 0.49000(8) 0.22646(15) 0.48092(4) 0.0170(2) Uani 1 1 d . . . . .
H4 H 0.5280 0.2465 0.4616 0.020 Uiso 1 1 calc R U . . .
C3 C 0.64968(8) 0.38152(16) 0.52068(4) 0.0193(2) Uani 1 1 d . . . . .
H3A H 0.6185 0.4601 0.4969 0.029 Uiso 1 1 calc R U . . .
H3B H 0.6679 0.2803 0.5061 0.029 Uiso 1 1 calc R U . . .
H3C H 0.7003 0.4397 0.5395 0.029 Uiso 1 1 calc R U . . .
C5 C 0.40895(8) 0.15859(15) 0.46234(4) 0.0181(2) Uani 1 1 d . . . . .
H5 H 0.3928 0.1324 0.4304 0.022 Uiso 1 1 calc R U . . .
C13 C 0.34628(8) 0.70648(15) 0.61194(4) 0.0191(2) Uani 1 1 d . . . . .
H13A H 0.3917 0.7217 0.5955 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3543 0.7896 0.6372 0.029 Uiso 1 1 calc R U . . .
H13C H 0.2901 0.7247 0.5906 0.029 Uiso 1 1 calc R U . . .
C14 C 0.28069(8) 0.49625(16) 0.65679(4) 0.0193(2) Uani 1 1 d . . . . .
H14A H 0.2252 0.5326 0.6373 0.029 Uiso 1 1 calc R U . . .
H14B H 0.2935 0.5629 0.6854 0.029 Uiso 1 1 calc R U . . .
H14C H 0.2783 0.3740 0.6640 0.029 Uiso 1 1 calc R U . . .
C19 C 0.88147(8) 0.33367(18) 0.77003(4) 0.0237(3) Uani 1 1 d . . . . .
H19A H 0.8652 0.2128 0.7650 0.036 Uiso 1 1 calc R U . . .
H19B H 0.8545 0.3822 0.7933 0.036 Uiso 1 1 calc R U . . .
H19C H 0.9441 0.3427 0.7808 0.036 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 N1 1.4280(12) . ?
O1 C7 1.3954(13) . ?
O2 N1 1.4626(12) . ?
O2 C12 1.4515(13) . ?
O3 C2 1.3610(13) . ?
O3 C3 1.4314(13) . ?
O4 C18 1.3752(13) . ?
O4 C19 1.4271(15) . ?
N1 C8 1.5216(14) . ?
C1 C7 1.3827(15) . ?
C1 C2 1.3918(15) . ?
C1 C8 1.5163(15) . ?
C21 H21 0.9500 . ?
C21 C15 1.3995(15) . ?
C21 C20 1.3854(15) . ?
C7 C6 1.3752(16) . ?
C15 C10 1.5223(15) . ?
C15 C16 1.3946(15) . ?
C2 C4 1.3999(16) . ?
C10 H10 1.0000 . ?
C10 C8 1.5654(15) . ?
C10 C11 1.5398(15) . ?
C20 H20 0.9500 . ?
C20 C18 1.3919(16) . ?
C8 C9 1.5270(15) . ?
C16 H16 0.9500 . ?
C16 C17 1.3950(15) . ?
C18 C17 1.3902(16) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C12 C11 1.5374(15) . ?
C12 C13 1.5171(16) . ?
C12 C14 1.5207(15) . ?
C17 H17 0.9500 . ?
C6 H6 0.9500 . ?
C6 C5 1.3916(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C4 H4 0.9500 . ?
C4 C5 1.3883(17) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C5 H5 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 N1 106.51(8) . . ?
C12 O2 N1 106.88(8) . . ?
C2 O3 C3 117.11(9) . . ?
C18 O4 C19 116.84(9) . . ?
O1 N1 O2 101.27(7) . . ?
O1 N1 C8 104.92(8) . . ?
O2 N1 C8 104.95(8) . . ?
C7 C1 C2 118.36(10) . . ?
C7 C1 C8 107.09(9) . . ?
C2 C1 C8 134.48(10) . . ?
C15 C21 H21 119.2 . . ?
C20 C21 H21 119.2 . . ?
C20 C21 C15 121.65(10) . . ?
C1 C7 O1 111.26(9) . . ?
C6 C7 O1 123.55(10) . . ?
C6 C7 C1 125.19(10) . . ?
C21 C15 C10 119.74(10) . . ?
C16 C15 C21 117.30(10) . . ?
C16 C15 C10 122.87(10) . . ?
O3 C2 C1 116.68(9) . . ?
O3 C2 C4 124.77(10) . . ?
C1 C2 C4 118.54(10) . . ?
C15 C10 H10 106.9 . . ?
C15 C10 C8 115.87(9) . . ?
C15 C10 C11 110.99(9) . . ?
C8 C10 H10 106.9 . . ?
C11 C10 H10 106.9 . . ?
C11 C10 C8 108.75(9) . . ?
C21 C20 H20 120.1 . . ?
C21 C20 C18 119.82(10) . . ?
C18 C20 H20 120.1 . . ?
N1 C8 C10 106.58(8) . . ?
N1 C8 C9 105.11(9) . . ?
C1 C8 N1 100.76(8) . . ?
C1 C8 C10 117.83(9) . . ?
C1 C8 C9 110.00(9) . . ?
C9 C8 C10 114.70(9) . . ?
C15 C16 H16 119.0 . . ?
C15 C16 C17 121.96(10) . . ?
C17 C16 H16 119.0 . . ?
O4 C18 C20 115.44(10) . . ?
O4 C18 C17 124.57(10) . . ?
C17 C18 C20 119.98(10) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O2 C12 C11 107.65(9) . . ?
O2 C12 C13 103.61(9) . . ?
O2 C12 C14 109.97(9) . . ?
C13 C12 C11 111.69(10) . . ?
C13 C12 C14 111.20(10) . . ?
C14 C12 C11 112.30(9) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.23(10) . . ?
C18 C17 H17 120.4 . . ?
C7 C6 H6 122.3 . . ?
C7 C6 C5 115.33(10) . . ?
C5 C6 H6 122.3 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 C10 110.36(9) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C2 C4 H4 119.7 . . ?
C5 C4 C2 120.53(10) . . ?
C5 C4 H4 119.7 . . ?
O3 C3 H3A 109.5 . . ?
O3 C3 H3B 109.5 . . ?
O3 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C6 C5 H5 119.0 . . ?
C4 C5 C6 122.05(10) . . ?
C4 C5 H5 119.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C8 C1 29.33(10) . . . . ?
O1 N1 C8 C10 152.86(8) . . . . ?
O1 N1 C8 C9 -85.00(9) . . . . ?
O1 C7 C6 C5 -179.24(10) . . . . ?
O2 N1 C8 C1 -76.96(9) . . . . ?
O2 N1 C8 C10 46.57(10) . . . . ?
O2 N1 C8 C9 168.71(8) . . . . ?
O2 C12 C11 C10 29.42(12) . . . . ?
O3 C2 C4 C5 178.84(11) . . . . ?
O4 C18 C17 C16 -177.87(10) . . . . ?
N1 O1 C7 C1 17.74(12) . . . . ?
N1 O1 C7 C6 -163.03(10) . . . . ?
N1 O2 C12 C11 41.77(10) . . . . ?
N1 O2 C12 C13 160.21(8) . . . . ?
N1 O2 C12 C14 -80.86(10) . . . . ?
C1 C7 C6 C5 -0.12(17) . . . . ?
C1 C2 C4 C5 -0.56(17) . . . . ?
C21 C15 C10 C8 108.68(11) . . . . ?
C21 C15 C10 C11 -126.65(11) . . . . ?
C21 C15 C16 C17 -2.60(17) . . . . ?
C21 C20 C18 O4 177.13(10) . . . . ?
C21 C20 C18 C17 -2.06(17) . . . . ?
C7 O1 N1 O2 79.37(9) . . . . ?
C7 O1 N1 C8 -29.61(10) . . . . ?
C7 C1 C2 O3 -179.10(10) . . . . ?
C7 C1 C2 C4 0.35(16) . . . . ?
C7 C1 C8 N1 -19.16(11) . . . . ?
C7 C1 C8 C10 -134.55(10) . . . . ?
C7 C1 C8 C9 91.42(11) . . . . ?
C7 C6 C5 C4 -0.10(17) . . . . ?
C15 C21 C20 C18 0.52(17) . . . . ?
C15 C10 C8 N1 147.84(9) . . . . ?
C15 C10 C8 C1 -99.98(11) . . . . ?
C15 C10 C8 C9 31.97(13) . . . . ?
C15 C10 C11 C12 167.66(9) . . . . ?
C15 C16 C17 C18 1.15(17) . . . . ?
C2 C1 C7 O1 179.20(9) . . . . ?
C2 C1 C7 C6 -0.01(18) . . . . ?
C2 C1 C8 N1 164.24(12) . . . . ?
C2 C1 C8 C10 48.85(17) . . . . ?
C2 C1 C8 C9 -85.18(15) . . . . ?
C2 C4 C5 C6 0.44(18) . . . . ?
C10 C15 C16 C17 -179.19(10) . . . . ?
C20 C21 C15 C10 178.45(10) . . . . ?
C20 C21 C15 C16 1.76(16) . . . . ?
C20 C18 C17 C16 1.24(17) . . . . ?
C8 C1 C7 O1 1.96(12) . . . . ?
C8 C1 C7 C6 -177.25(11) . . . . ?
C8 C1 C2 O3 -2.79(19) . . . . ?
C8 C1 C2 C4 176.65(11) . . . . ?
C8 C10 C11 C12 -63.74(11) . . . . ?
C16 C15 C10 C8 -74.82(13) . . . . ?
C16 C15 C10 C11 49.85(14) . . . . ?
C12 O2 N1 O1 164.45(7) . . . . ?
C12 O2 N1 C8 -86.58(9) . . . . ?
C11 C10 C8 N1 22.03(11) . . . . ?
C11 C10 C8 C1 134.21(10) . . . . ?
C11 C10 C8 C9 -93.84(11) . . . . ?
C3 O3 C2 C1 -171.91(10) . . . . ?
C3 O3 C2 C4 8.68(16) . . . . ?
C13 C12 C11 C10 -83.68(11) . . . . ?
C14 C12 C11 C10 150.60(10) . . . . ?
C19 O4 C18 C20 -178.22(10) . . . . ?
C19 O4 C18 C17 0.93(17) . . . . ?

_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_AL364
_database_code_depnum_ccdc_archive 'CCDC 2240874'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-02-09 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-02-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O2'
_chemical_formula_sum            'C14 H19 N O2'
_chemical_formula_weight         233.30
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.3557(2)
_cell_length_b                   12.0543(3)
_cell_length_c                   12.7272(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.3530(10)
_cell_angle_gamma                90
_cell_volume                     1268.31(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4324
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1426 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.8973.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14324
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.994
_diffrn_reflns_theta_min         2.339
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest D8 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2324
_reflns_number_total             2769
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2769
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.045
_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)+(0.0381P)²+0.5107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0917
_refine_ls_wR_factor_ref         0.0978
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_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 0.57642(10) 0.68457(7) 0.68505(7) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.33356(10) 0.77515(7) 0.63216(7) 0.0149(2) Uani 1 1 d . . . . .
N1 N 0.41099(12) 0.71039(8) 0.71408(8) 0.0139(2) Uani 1 1 d . . . . .
C1 C 0.61158(15) 0.58135(10) 0.72651(10) 0.0137(3) Uani 1 1 d . . . . .
C2 C 0.47780(15) 0.52602(10) 0.75219(10) 0.0136(3) Uani 1 1 d . . . . .
C3 C 0.32992(15) 0.59788(10) 0.72468(10) 0.0132(3) Uani 1 1 d . . . . .
C4 C 0.22098(15) 0.56455(10) 0.62109(10) 0.0158(3) Uani 1 1 d . . . . .
H4 H 0.1163 0.6053 0.6189 0.019 Uiso 1 1 calc R U . . .
C5 C 0.29928(16) 0.60324(10) 0.52674(10) 0.0166(3) Uani 1 1 d . . . . .
H5A H 0.4098 0.5720 0.5322 0.020 Uiso 1 1 calc R U . . .
H5B H 0.2358 0.5752 0.4603 0.020 Uiso 1 1 calc R U . . .
C6 C 0.30827(16) 0.72920(10) 0.52224(10) 0.0159(3) Uani 1 1 d . . . . .
C7 C 0.76599(15) 0.53710(11) 0.74361(10) 0.0171(3) Uani 1 1 d . . . . .
H7 H 0.8561 0.5765 0.7247 0.021 Uiso 1 1 calc R U . . .
C8 C 0.78348(16) 0.43242(11) 0.78962(11) 0.0201(3) Uani 1 1 d . . . . .
H8 H 0.8875 0.3990 0.8020 0.024 Uiso 1 1 calc R U . . .
C9 C 0.65108(17) 0.37591(11) 0.81776(11) 0.0212(3) Uani 1 1 d . . . . .
H9 H 0.6659 0.3049 0.8500 0.025 Uiso 1 1 calc R U . . .
C10 C 0.49673(16) 0.42225(10) 0.79919(11) 0.0180(3) Uani 1 1 d . . . . .
H10 H 0.4063 0.3835 0.8184 0.022 Uiso 1 1 calc R U . . .
C11 C 0.14785(16) 0.78037(11) 0.47371(11) 0.0205(3) Uani 1 1 d . . . . .
H11A H 0.0619 0.7545 0.5125 0.031 Uiso 1 1 calc R U . . .
H11B H 0.1229 0.7582 0.3991 0.031 Uiso 1 1 calc R U . . .
H11C H 0.1555 0.8614 0.4783 0.031 Uiso 1 1 calc R U . . .
C12 C 0.44383(18) 0.77021(12) 0.46445(11) 0.0247(3) Uani 1 1 d . . . . .
H12A H 0.4473 0.8514 0.4665 0.037 Uiso 1 1 calc R U . . .
H12B H 0.4243 0.7452 0.3904 0.037 Uiso 1 1 calc R U . . .
H12C H 0.5473 0.7404 0.4991 0.037 Uiso 1 1 calc R U . . .
C13 C 0.18248(18) 0.44072(11) 0.61444(12) 0.0245(3) Uani 1 1 d . . . . .
H13A H 0.2816 0.3989 0.6093 0.037 Uiso 1 1 calc R U . . .
H13B H 0.1028 0.4261 0.5515 0.037 Uiso 1 1 calc R U . . .
H13C H 0.1383 0.4176 0.6783 0.037 Uiso 1 1 calc R U . . .
C14 C 0.23278(16) 0.61121(12) 0.81643(11) 0.0204(3) Uani 1 1 d . . . . .
H14A H 0.3057 0.6313 0.8810 0.031 Uiso 1 1 calc R U . . .
H14B H 0.1784 0.5411 0.8279 0.031 Uiso 1 1 calc R U . . .
H14C H 0.1518 0.6697 0.7993 0.031 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 N1 1.5140(13) . ?
O1 C1 1.3667(14) . ?
O2 N1 1.3853(13) . ?
O2 C6 1.4909(15) . ?
N1 C3 1.5306(15) . ?
C1 C2 1.3811(17) . ?
C1 C7 1.3838(17) . ?
C2 C3 1.5079(17) . ?
C2 C10 1.3857(17) . ?
C3 C4 1.5426(17) . ?
C3 C14 1.5243(18) . ?
C4 H4 1.0000 . ?
C4 C5 1.5218(18) . ?
C4 C13 1.5267(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5216(17) . ?
C6 C11 1.5226(18) . ?
C6 C12 1.5200(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3898(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.3938(18) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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 O1 N1 104.22(9) . . ?
N1 O2 C6 118.94(9) . . ?
O1 N1 C3 105.71(8) . . ?
O2 N1 O1 105.98(8) . . ?
O2 N1 C3 113.66(9) . . ?
O1 C1 C2 113.26(11) . . ?
O1 C1 C7 123.71(11) . . ?
C2 C1 C7 123.01(12) . . ?
C1 C2 C3 109.38(10) . . ?
C1 C2 C10 119.51(12) . . ?
C10 C2 C3 131.08(12) . . ?
N1 C3 C4 111.66(10) . . ?
C2 C3 N1 99.86(9) . . ?
C2 C3 C4 114.25(10) . . ?
C2 C3 C14 113.09(10) . . ?
C14 C3 N1 105.42(10) . . ?
C14 C3 C4 111.62(10) . . ?
C3 C4 H4 107.6 . . ?
C5 C4 C3 109.07(10) . . ?
C5 C4 H4 107.6 . . ?
C5 C4 C13 111.55(11) . . ?
C13 C4 C3 113.30(10) . . ?
C13 C4 H4 107.6 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.39(10) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
O2 C6 C5 109.66(10) . . ?
O2 C6 C11 103.09(10) . . ?
O2 C6 C12 108.62(10) . . ?
C5 C6 C11 111.97(11) . . ?
C12 C6 C5 112.77(11) . . ?
C12 C6 C11 110.23(11) . . ?
C1 C7 H7 121.5 . . ?
C1 C7 C8 117.05(12) . . ?
C8 C7 H7 121.5 . . ?
C7 C8 H8 119.5 . . ?
C9 C8 C7 120.98(12) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.77(12) . . ?
C10 C9 H9 119.6 . . ?
C2 C10 C9 118.67(12) . . ?
C2 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C4 C13 H13A 109.5 . . ?
C4 C13 H13B 109.5 . . ?
C4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 N1 C3 C2 25.77(11) . . . . ?
O1 N1 C3 C4 -95.40(11) . . . . ?
O1 N1 C3 C14 143.21(9) . . . . ?
O1 C1 C2 C3 0.67(14) . . . . ?
O1 C1 C2 C10 -177.29(11) . . . . ?
O1 C1 C7 C8 177.92(11) . . . . ?
O2 N1 C3 C2 141.59(9) . . . . ?
O2 N1 C3 C4 20.42(13) . . . . ?
O2 N1 C3 C14 -100.96(11) . . . . ?
N1 O1 C1 C2 16.34(13) . . . . ?
N1 O1 C1 C7 -162.22(11) . . . . ?
N1 O2 C6 C5 27.17(14) . . . . ?
N1 O2 C6 C11 146.58(10) . . . . ?
N1 O2 C6 C12 -96.48(12) . . . . ?
N1 C3 C4 C5 36.26(13) . . . . ?
N1 C3 C4 C13 161.14(11) . . . . ?
C1 O1 N1 O2 -147.58(9) . . . . ?
C1 O1 N1 C3 -26.63(11) . . . . ?
C1 C2 C3 N1 -16.90(13) . . . . ?
C1 C2 C3 C4 102.39(12) . . . . ?
C1 C2 C3 C14 -128.46(12) . . . . ?
C1 C2 C10 C9 -0.95(19) . . . . ?
C1 C7 C8 C9 -0.57(19) . . . . ?
C2 C1 C7 C8 -0.51(19) . . . . ?
C2 C3 C4 C5 -76.13(13) . . . . ?
C2 C3 C4 C13 48.75(15) . . . . ?
C3 C2 C10 C9 -178.40(13) . . . . ?
C3 C4 C5 C6 -64.91(13) . . . . ?
C4 C5 C6 O2 33.55(14) . . . . ?
C4 C5 C6 C11 -80.25(13) . . . . ?
C4 C5 C6 C12 154.73(11) . . . . ?
C6 O2 N1 O1 59.37(11) . . . . ?
C6 O2 N1 C3 -56.29(13) . . . . ?
C7 C1 C2 C3 179.25(11) . . . . ?
C7 C1 C2 C10 1.29(19) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C2 -0.1(2) . . . . ?
C10 C2 C3 N1 160.75(13) . . . . ?
C10 C2 C3 C4 -79.96(17) . . . . ?
C10 C2 C3 C14 49.19(18) . . . . ?
C13 C4 C5 C6 169.19(11) . . . . ?
C14 C3 C4 C5 153.98(10) . . . . ?
C14 C3 C4 C13 -81.14(14) . . . . ?

_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_al273
_database_code_depnum_ccdc_archive 'CCDC 2250118'
loop_
_audit_author_name
_audit_author_address
'Svetlana Aksenova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2023-03-20 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 N O3'
_chemical_formula_sum            'C23 H21 N O3'
_chemical_formula_weight         359.41
_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                   9.3222(2)
_cell_length_b                   9.7350(2)
_cell_length_c                   20.5787(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.0680(10)
_cell_angle_gamma                90
_cell_volume                     1838.79(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9945
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.58
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0790 before and 0.0435 after correction.
The Ratio of minimum to maximum transmission is 0.9358.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            23650
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.010
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4459
_reflns_number_total             4893
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4893
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0438
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.046
_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)+(0.0525P)²+0.6728P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1066
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C17(H17)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C16(H16), C15(H15), C19(H19), C23(H23), C3(H3), C6(H6),
 C20(H20), C21(H21), C22(H22), C5(H5), C4(H4)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C14(H14A,H14B,H14C)
;
_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 0.36694(7) 0.61372(7) 0.29189(3) 0.01699(15) Uani 1 1 d . . . . .
O1 O 0.52932(8) 0.73974(8) 0.36527(4) 0.02086(16) Uani 1 1 d . . . . .
O3 O 0.78689(8) 0.06766(8) 0.53001(4) 0.02208(17) Uani 1 1 d . . . . .
N1 N 0.50683(9) 0.66744(8) 0.29915(4) 0.01603(17) Uani 1 1 d . . . . .
C10 C 0.58212(10) 0.33085(9) 0.38180(5) 0.01403(18) Uani 1 1 d . . . . .
C9 C 0.51446(10) 0.42151(9) 0.32517(4) 0.01332(17) Uani 1 1 d . . . . .
H9 H 0.4953 0.3624 0.2848 0.016 Uiso 1 1 calc R U . . .
C13 C 0.71684(10) 0.15727(10) 0.48389(5) 0.01719(19) Uani 1 1 d . . . . .
C17 C 0.36972(10) 0.48999(10) 0.33207(5) 0.01501(18) Uani 1 1 d . . . . .
H17 H 0.3691 0.5147 0.3792 0.018 Uiso 1 1 calc R U . . .
C1 C 0.61066(10) 0.54554(9) 0.30928(5) 0.01437(17) Uani 1 1 d . . . . .
C11 C 0.67564(11) 0.22546(10) 0.36959(5) 0.01746(19) Uani 1 1 d . . . . .
H11 H 0.6930 0.2116 0.3259 0.021 Uiso 1 1 calc R U . . .
C2 C 0.72354(11) 0.59467(10) 0.36550(5) 0.01735(19) Uani 1 1 d . . . . .
C7 C 0.66771(11) 0.70503(10) 0.39500(5) 0.0192(2) Uani 1 1 d . . . . .
C12 C 0.74365(11) 0.14067(10) 0.41971(5) 0.0197(2) Uani 1 1 d . . . . .
H12 H 0.8086 0.0711 0.4104 0.024 Uiso 1 1 calc R U . . .
C18 C 0.23717(10) 0.40706(10) 0.30471(5) 0.01777(19) Uani 1 1 d . . . . .
C8 C 0.66645(12) 0.52275(11) 0.24497(5) 0.0209(2) Uani 1 1 d . . . . .
H8A H 0.5839 0.5056 0.2093 0.031 Uiso 1 1 calc R U . . .
H8B H 0.7321 0.4434 0.2496 0.031 Uiso 1 1 calc R U . . .
H8C H 0.7193 0.6046 0.2345 0.031 Uiso 1 1 calc R U . . .
C16 C 0.55811(11) 0.34635(10) 0.44621(5) 0.0199(2) Uani 1 1 d . . . . .
H16 H 0.4954 0.4176 0.4558 0.024 Uiso 1 1 calc R U . . .
C15 C 0.62353(11) 0.26026(11) 0.49723(5) 0.0199(2) Uani 1 1 d . . . . .
H15 H 0.6042 0.2722 0.5407 0.024 Uiso 1 1 calc R U . . .
C19 C 0.18972(11) 0.39887(11) 0.23664(5) 0.0220(2) Uani 1 1 d . . . . .
H19 H 0.2406 0.4471 0.2076 0.026 Uiso 1 1 calc R U . . .
C23 C 0.16373(11) 0.33416(11) 0.34690(6) 0.0243(2) Uani 1 1 d . . . . .
H23 H 0.1951 0.3393 0.3933 0.029 Uiso 1 1 calc R U . . .
C3 C 0.86443(12) 0.55066(11) 0.38842(6) 0.0262(2) Uani 1 1 d . . . . .
H3 H 0.9040 0.4746 0.3686 0.031 Uiso 1 1 calc R U . . .
C6 C 0.74618(14) 0.77510(12) 0.44823(5) 0.0277(2) Uani 1 1 d . . . . .
H6 H 0.7053 0.8498 0.4684 0.033 Uiso 1 1 calc R U . . .
C20 C 0.06849(12) 0.32053(12) 0.21117(6) 0.0283(2) Uani 1 1 d . . . . .
H20 H 0.0354 0.3168 0.1648 0.034 Uiso 1 1 calc R U . . .
C21 C -0.00450(12) 0.24761(12) 0.25332(8) 0.0325(3) Uani 1 1 d . . . . .
H21 H -0.0874 0.1939 0.2359 0.039 Uiso 1 1 calc R U . . .
C22 C 0.04369(12) 0.25333(12) 0.32078(7) 0.0314(3) Uani 1 1 d . . . . .
H22 H -0.0052 0.2019 0.3495 0.038 Uiso 1 1 calc R U . . .
C5 C 0.88802(14) 0.73038(14) 0.47067(6) 0.0330(3) Uani 1 1 d . . . . .
H5 H 0.9457 0.7760 0.5069 0.040 Uiso 1 1 calc R U . . .
C4 C 0.94707(13) 0.62074(13) 0.44136(6) 0.0328(3) Uani 1 1 d . . . . .
H4 H 1.0445 0.5930 0.4574 0.039 Uiso 1 1 calc R U . . .
C14 C 0.74022(14) 0.06569(13) 0.59245(5) 0.0298(3) Uani 1 1 d . . . . .
H14A H 0.6353 0.0472 0.5859 0.045 Uiso 1 1 calc R U . . .
H14B H 0.7605 0.1549 0.6141 0.045 Uiso 1 1 calc R U . . .
H14C H 0.7928 -0.0064 0.6202 0.045 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
O2 N1 1.3887(10) . ?
O2 C17 1.4586(11) . ?
O1 N1 1.5135(11) . ?
O1 C7 1.3700(13) . ?
O3 C13 1.3680(11) . ?
O3 C14 1.4271(13) . ?
N1 C1 1.5225(12) . ?
C10 C9 1.5092(12) . ?
C10 C11 1.3974(13) . ?
C10 C16 1.3906(13) . ?
C9 H9 1.0000 . ?
C9 C17 1.5336(12) . ?
C9 C1 1.5721(13) . ?
C13 C12 1.3959(13) . ?
C13 C15 1.3859(13) . ?
C17 H17 1.0000 . ?
C17 C18 1.5008(13) . ?
C1 C2 1.4997(13) . ?
C1 C8 1.5204(13) . ?
C11 H11 0.9500 . ?
C11 C12 1.3851(13) . ?
C2 C7 1.3799(14) . ?
C2 C3 1.3836(14) . ?
C7 C6 1.3858(14) . ?
C12 H12 0.9500 . ?
C18 C19 1.3956(14) . ?
C18 C23 1.3907(14) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C16 H16 0.9500 . ?
C16 C15 1.3973(14) . ?
C15 H15 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.3880(15) . ?
C23 H23 0.9500 . ?
C23 C22 1.3965(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3972(17) . ?
C6 H6 0.9500 . ?
C6 C5 1.3920(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.3876(19) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(2) . ?
C22 H22 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.386(2) . ?
C4 H4 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
N1 O2 C17 109.07(7) . . ?
C7 O1 N1 104.97(7) . . ?
C13 O3 C14 116.71(8) . . ?
O2 N1 O1 104.58(6) . . ?
O2 N1 C1 106.49(7) . . ?
O1 N1 C1 104.75(7) . . ?
C11 C10 C9 118.70(8) . . ?
C16 C10 C9 123.88(8) . . ?
C16 C10 C11 117.42(9) . . ?
C10 C9 H9 107.1 . . ?
C10 C9 C17 116.00(7) . . ?
C10 C9 C1 115.67(7) . . ?
C17 C9 H9 107.1 . . ?
C17 C9 C1 103.21(7) . . ?
C1 C9 H9 107.1 . . ?
O3 C13 C12 116.09(8) . . ?
O3 C13 C15 124.33(9) . . ?
C15 C13 C12 119.57(9) . . ?
O2 C17 C9 103.61(7) . . ?
O2 C17 H17 110.4 . . ?
O2 C17 C18 107.44(7) . . ?
C9 C17 H17 110.4 . . ?
C18 C17 C9 114.30(8) . . ?
C18 C17 H17 110.4 . . ?
N1 C1 C9 104.77(7) . . ?
C2 C1 N1 101.57(7) . . ?
C2 C1 C9 115.68(8) . . ?
C2 C1 C8 114.67(8) . . ?
C8 C1 N1 107.50(8) . . ?
C8 C1 C9 111.31(8) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.49(9) . . ?
C12 C11 H11 119.3 . . ?
C7 C2 C1 108.66(8) . . ?
C7 C2 C3 119.98(10) . . ?
C3 C2 C1 131.33(10) . . ?
O1 C7 C2 113.19(9) . . ?
O1 C7 C6 123.87(10) . . ?
C2 C7 C6 122.91(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.08(9) . . ?
C11 C12 H12 120.0 . . ?
C19 C18 C17 120.19(9) . . ?
C23 C18 C17 120.22(9) . . ?
C23 C18 C19 119.55(10) . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C16 H16 119.0 . . ?
C10 C16 C15 121.96(9) . . ?
C15 C16 H16 119.0 . . ?
C13 C15 C16 119.45(9) . . ?
C13 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.31(11) . . ?
C20 C19 H19 119.8 . . ?
C18 C23 H23 120.1 . . ?
C18 C23 C22 119.74(11) . . ?
C22 C23 H23 120.1 . . ?
C2 C3 H3 120.8 . . ?
C2 C3 C4 118.41(11) . . ?
C4 C3 H3 120.8 . . ?
C7 C6 H6 121.7 . . ?
C7 C6 C5 116.61(11) . . ?
C5 C6 H6 121.7 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 C19 120.06(12) . . ?
C21 C20 H20 120.0 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.86(11) . . ?
C22 C21 H21 120.1 . . ?
C23 C22 H22 119.8 . . ?
C21 C22 C23 120.45(11) . . ?
C21 C22 H22 119.8 . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.52(11) . . ?
C4 C5 H5 119.2 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.56(11) . . ?
C5 C4 H4 119.7 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C9 -14.33(9) . . . . ?
O2 N1 C1 C2 -135.09(7) . . . . ?
O2 N1 C1 C8 104.16(8) . . . . ?
O2 C17 C18 C19 38.70(11) . . . . ?
O2 C17 C18 C23 -143.48(9) . . . . ?
O1 N1 C1 C9 96.12(7) . . . . ?
O1 N1 C1 C2 -24.64(8) . . . . ?
O1 N1 C1 C8 -145.39(7) . . . . ?
O1 C7 C6 C5 -177.12(9) . . . . ?
O3 C13 C12 C11 179.01(9) . . . . ?
O3 C13 C15 C16 179.81(10) . . . . ?
N1 O2 C17 C9 -37.57(9) . . . . ?
N1 O2 C17 C18 -158.89(7) . . . . ?
N1 O1 C7 C2 -15.52(10) . . . . ?
N1 O1 C7 C6 162.89(9) . . . . ?
N1 C1 C2 C7 16.39(10) . . . . ?
N1 C1 C2 C3 -161.71(10) . . . . ?
C10 C9 C17 O2 153.39(7) . . . . ?
C10 C9 C17 C18 -90.01(10) . . . . ?
C10 C9 C1 N1 -135.43(8) . . . . ?
C10 C9 C1 C2 -24.52(11) . . . . ?
C10 C9 C1 C8 108.68(9) . . . . ?
C10 C11 C12 C13 1.53(16) . . . . ?
C10 C16 C15 C13 0.90(16) . . . . ?
C9 C10 C11 C12 178.57(9) . . . . ?
C9 C10 C16 C15 -179.76(9) . . . . ?
C9 C17 C18 C19 -75.66(11) . . . . ?
C9 C17 C18 C23 102.16(10) . . . . ?
C9 C1 C2 C7 -96.39(9) . . . . ?
C9 C1 C2 C3 85.51(13) . . . . ?
C17 O2 N1 O1 -77.78(8) . . . . ?
C17 O2 N1 C1 32.79(9) . . . . ?
C17 C9 C1 N1 -7.67(9) . . . . ?
C17 C9 C1 C2 103.24(9) . . . . ?
C17 C9 C1 C8 -123.55(8) . . . . ?
C17 C18 C19 C20 179.00(9) . . . . ?
C17 C18 C23 C22 -177.67(9) . . . . ?
C1 C9 C17 O2 25.84(9) . . . . ?
C1 C9 C17 C18 142.44(8) . . . . ?
C1 C2 C7 O1 -0.78(11) . . . . ?
C1 C2 C7 C6 -179.21(9) . . . . ?
C1 C2 C3 C4 177.70(10) . . . . ?
C11 C10 C9 C17 154.57(9) . . . . ?
C11 C10 C9 C1 -84.34(10) . . . . ?
C11 C10 C16 C15 -0.34(15) . . . . ?
C2 C7 C6 C5 1.14(16) . . . . ?
C2 C3 C4 C5 0.96(17) . . . . ?
C7 O1 N1 O2 136.97(7) . . . . ?
C7 O1 N1 C1 25.15(9) . . . . ?
C7 C2 C3 C4 -0.22(16) . . . . ?
C7 C6 C5 C4 -0.37(17) . . . . ?
C12 C13 C15 C16 -0.26(15) . . . . ?
C18 C19 C20 C21 -1.31(16) . . . . ?
C18 C23 C22 C21 -1.38(17) . . . . ?
C8 C1 C2 C7 131.97(9) . . . . ?
C8 C1 C2 C3 -46.13(14) . . . . ?
C16 C10 C9 C17 -26.02(13) . . . . ?
C16 C10 C9 C1 95.08(11) . . . . ?
C16 C10 C11 C12 -0.88(15) . . . . ?
C15 C13 C12 C11 -0.93(16) . . . . ?
C19 C18 C23 C22 0.17(15) . . . . ?
C19 C20 C21 C22 0.10(17) . . . . ?
C23 C18 C19 C20 1.16(15) . . . . ?
C3 C2 C7 O1 177.57(9) . . . . ?
C3 C2 C7 C6 -0.86(15) . . . . ?
C6 C5 C4 C3 -0.66(18) . . . . ?
C20 C21 C22 C23 1.24(18) . . . . ?
C14 O3 C13 C12 -168.45(10) . . . . ?
C14 O3 C13 C15 11.48(15) . . . . ?

_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_AL279
_database_code_depnum_ccdc_archive 'CCDC 2237938'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H22 Cl N O7'
_chemical_formula_sum            'C22 H22 Cl N O7'
_chemical_formula_weight         447.85
_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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           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                   8.2903(2)
_cell_length_b                   11.3338(3)
_cell_length_c                   12.6044(3)
_cell_angle_alpha                65.4040(10)
_cell_angle_beta                 81.0380(10)
_cell_angle_gamma                82.3700(10)
_cell_volume                     1060.66(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7778
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.61
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.225
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0925 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.9036.
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    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13623
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4899
_reflns_number_total             5625
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5625
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.031
_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)+(0.0376P)²+0.4688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0838
_refine_ls_wR_factor_ref         0.0878
_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:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C)
;
_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
Cl1 Cl -0.16583(4) -0.35661(3) -0.81771(3) 0.01903(8) Uani 1 1 d . . . . .
O1 O -0.49386(11) -0.14330(8) -0.91280(7) 0.01784(18) Uani 1 1 d . . . . .
O2 O -0.62503(10) -0.32966(8) -0.85575(7) 0.01548(17) Uani 1 1 d . . . . .
O3 O -0.75719(12) -0.63198(9) -0.63970(8) 0.0225(2) Uani 1 1 d . . . . .
O4 O -0.78488(11) -0.51663(8) -0.83184(7) 0.01707(18) Uani 1 1 d . . . . .
O5 O -0.71686(12) -0.42103(9) -0.54788(8) 0.02088(19) Uani 1 1 d . . . . .
O6 O -0.85548(11) -0.29042(9) -0.70095(8) 0.0224(2) Uani 1 1 d . . . . .
O7 O -0.15065(11) -0.89545(8) -0.81588(8) 0.01960(19) Uani 1 1 d . . . . .
N1 N -0.46240(12) -0.27955(9) -0.89044(9) 0.01449(19) Uani 1 1 d . . . . .
C1 C -0.48429(15) -0.13086(11) -0.80916(10) 0.0152(2) Uani 1 1 d . . . . .
C2 C -0.42137(14) -0.24390(11) -0.72500(10) 0.0135(2) Uani 1 1 d . . . . .
C3 C -0.38210(14) -0.34201(11) -0.77807(10) 0.0134(2) Uani 1 1 d . . . . .
C4 C -0.45757(14) -0.47296(11) -0.71025(10) 0.0125(2) Uani 1 1 d . . . . .
H4 H -0.4535 -0.5002 -0.6243 0.015 Uiso 1 1 calc R U . . .
C5 C -0.63613(14) -0.42823(11) -0.73856(10) 0.0127(2) Uani 1 1 d . . . . .
C6 C -0.52573(16) -0.01714(12) -0.79220(11) 0.0190(2) Uani 1 1 d . . . . .
H6 H -0.5688 0.0600 -0.8511 0.023 Uiso 1 1 calc R U . . .
C7 C -0.50051(16) -0.02265(12) -0.68353(11) 0.0197(2) Uani 1 1 d . . . . .
H7 H -0.5267 0.0532 -0.6679 0.024 Uiso 1 1 calc R U . . .
C8 C -0.43795(16) -0.13606(12) -0.59689(11) 0.0186(2) Uani 1 1 d . . . . .
H8 H -0.4226 -0.1362 -0.5237 0.022 Uiso 1 1 calc R U . . .
C9 C -0.39763(15) -0.24929(12) -0.61652(10) 0.0159(2) Uani 1 1 d . . . . .
H9 H -0.3555 -0.3271 -0.5578 0.019 Uiso 1 1 calc R U . . .
C10 C -0.73162(14) -0.53966(11) -0.73097(10) 0.0141(2) Uani 1 1 d . . . . .
C11 C -0.88872(16) -0.61288(12) -0.82970(12) 0.0205(3) Uani 1 1 d . . . . .
H11A H -0.9547 -0.5728 -0.8968 0.025 Uiso 1 1 calc R U . . .
H11B H -0.9650 -0.6399 -0.7565 0.025 Uiso 1 1 calc R U . . .
C12 C -0.78778(17) -0.73067(13) -0.83641(13) 0.0241(3) Uani 1 1 d . . . . .
H12A H -0.7294 -0.7746 -0.7666 0.036 Uiso 1 1 calc R U . . .
H12B H -0.7084 -0.7036 -0.9069 0.036 Uiso 1 1 calc R U . . .
H12C H -0.8598 -0.7905 -0.8401 0.036 Uiso 1 1 calc R U . . .
C13 C -0.73803(14) -0.37797(11) -0.64976(11) 0.0156(2) Uani 1 1 d . . . . .
C14 C -0.97476(17) -0.24525(16) -0.62481(14) 0.0297(3) Uani 1 1 d . . . . .
H14A H -0.9909 -0.3170 -0.5461 0.036 Uiso 1 1 calc R U . . .
H14B H -1.0812 -0.2204 -0.6576 0.036 Uiso 1 1 calc R U . . .
C15 C -0.91900(19) -0.13081(14) -0.61351(13) 0.0287(3) Uani 1 1 d . . . . .
H15A H -1.0009 -0.1032 -0.5617 0.043 Uiso 1 1 calc R U . . .
H15B H -0.9055 -0.0590 -0.6912 0.043 Uiso 1 1 calc R U . . .
H15C H -0.8142 -0.1555 -0.5802 0.043 Uiso 1 1 calc R U . . .
C16 C -0.37994(14) -0.58230(11) -0.74480(10) 0.0131(2) Uani 1 1 d . . . . .
C17 C -0.37200(15) -0.57728(11) -0.85764(10) 0.0165(2) Uani 1 1 d . . . . .
H17 H -0.4186 -0.5024 -0.9169 0.020 Uiso 1 1 calc R U . . .
C18 C -0.29702(15) -0.68005(11) -0.88571(10) 0.0161(2) Uani 1 1 d . . . . .
H18 H -0.2927 -0.6752 -0.9632 0.019 Uiso 1 1 calc R U . . .
C19 C -0.22878(14) -0.78956(11) -0.79896(10) 0.0149(2) Uani 1 1 d . . . . .
C20 C -0.23658(15) -0.79647(11) -0.68515(10) 0.0168(2) Uani 1 1 d . . . . .
H20 H -0.1913 -0.8718 -0.6256 0.020 Uiso 1 1 calc R U . . .
C21 C -0.31038(15) -0.69337(11) -0.65913(10) 0.0152(2) Uani 1 1 d . . . . .
H21 H -0.3138 -0.6982 -0.5818 0.018 Uiso 1 1 calc R U . . .
C22 C -0.14248(18) -0.89471(13) -0.93034(12) 0.0252(3) Uani 1 1 d . . . . .
H22A H -0.0899 -0.9777 -0.9296 0.038 Uiso 1 1 calc R U . . .
H22B H -0.0785 -0.8234 -0.9870 0.038 Uiso 1 1 calc R U . . .
H22C H -0.2534 -0.8825 -0.9528 0.038 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
Cl1 C3 1.7896(12) . ?
O1 N1 1.4442(12) . ?
O1 C1 1.3861(14) . ?
O2 N1 1.4644(13) . ?
O2 C5 1.4317(13) . ?
O3 C10 1.2017(14) . ?
O4 C10 1.3219(14) . ?
O4 C11 1.4661(14) . ?
O5 C13 1.2015(15) . ?
O6 C13 1.3248(15) . ?
O6 C14 1.4629(16) . ?
O7 C19 1.3671(14) . ?
O7 C22 1.4303(15) . ?
N1 C3 1.5114(14) . ?
C1 C2 1.3792(16) . ?
C1 C6 1.3835(16) . ?
C2 C3 1.4983(15) . ?
C2 C9 1.3869(16) . ?
C3 C4 1.5326(15) . ?
C4 H4 1.0000 . ?
C4 C5 1.5461(16) . ?
C4 C16 1.5132(15) . ?
C5 C10 1.5402(16) . ?
C5 C13 1.5490(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3923(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3945(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.3945(16) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5050(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.500(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.3909(16) . ?
C16 C21 1.3975(16) . ?
C17 H17 0.9500 . ?
C17 C18 1.3966(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3902(16) . ?
C19 C20 1.3954(16) . ?
C20 H20 0.9500 . ?
C20 C21 1.3835(16) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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 O1 N1 107.64(8) . . ?
C5 O2 N1 110.74(8) . . ?
C10 O4 C11 115.82(9) . . ?
C13 O6 C14 116.60(11) . . ?
C19 O7 C22 117.52(10) . . ?
O1 N1 O2 104.13(8) . . ?
O1 N1 C3 105.91(8) . . ?
O2 N1 C3 103.47(8) . . ?
C2 C1 O1 112.37(10) . . ?
C2 C1 C6 123.04(11) . . ?
C6 C1 O1 124.53(11) . . ?
C1 C2 C3 107.39(10) . . ?
C1 C2 C9 120.87(11) . . ?
C9 C2 C3 131.66(11) . . ?
N1 C3 Cl1 107.50(8) . . ?
N1 C3 C4 104.92(9) . . ?
C2 C3 Cl1 109.50(8) . . ?
C2 C3 N1 103.49(9) . . ?
C2 C3 C4 116.63(9) . . ?
C4 C3 Cl1 113.77(8) . . ?
C3 C4 H4 109.1 . . ?
C3 C4 C5 98.66(8) . . ?
C5 C4 H4 109.1 . . ?
C16 C4 C3 115.45(9) . . ?
C16 C4 H4 109.1 . . ?
C16 C4 C5 114.81(9) . . ?
O2 C5 C4 105.77(9) . . ?
O2 C5 C10 109.98(9) . . ?
O2 C5 C13 112.04(9) . . ?
C4 C5 C13 112.37(9) . . ?
C10 C5 C4 112.79(9) . . ?
C10 C5 C13 104.02(9) . . ?
C1 C6 H6 122.0 . . ?
C1 C6 C7 115.92(11) . . ?
C7 C6 H6 122.0 . . ?
C6 C7 H7 119.0 . . ?
C6 C7 C8 122.02(11) . . ?
C8 C7 H7 119.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.72(11) . . ?
C9 C8 H8 119.6 . . ?
C2 C9 C8 117.42(11) . . ?
C2 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
O3 C10 O4 126.57(11) . . ?
O3 C10 C5 121.01(10) . . ?
O4 C10 C5 112.34(10) . . ?
O4 C11 H11A 109.4 . . ?
O4 C11 H11B 109.4 . . ?
O4 C11 C12 111.35(10) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 O6 126.57(11) . . ?
O5 C13 C5 123.15(11) . . ?
O6 C13 C5 110.10(10) . . ?
O6 C14 H14A 109.3 . . ?
O6 C14 H14B 109.3 . . ?
O6 C14 C15 111.39(12) . . ?
H14A C14 H14B 108.0 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C4 123.50(10) . . ?
C17 C16 C21 118.31(10) . . ?
C21 C16 C4 118.18(10) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.40(11) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.22(11) . . ?
C19 C18 H18 120.4 . . ?
O7 C19 C18 124.69(11) . . ?
O7 C19 C20 115.22(10) . . ?
C18 C19 C20 120.09(11) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 C19 119.88(11) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 121.08(11) . . ?
C20 C21 H21 119.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
Cl1 C3 C4 C5 -156.98(7) . . . . ?
Cl1 C3 C4 C16 -34.12(12) . . . . ?
O1 N1 C3 Cl1 -98.64(8) . . . . ?
O1 N1 C3 C2 17.19(11) . . . . ?
O1 N1 C3 C4 139.93(9) . . . . ?
O1 C1 C2 C3 0.95(13) . . . . ?
O1 C1 C2 C9 177.98(10) . . . . ?
O1 C1 C6 C7 -177.14(11) . . . . ?
O2 N1 C3 Cl1 152.13(7) . . . . ?
O2 N1 C3 C2 -92.04(9) . . . . ?
O2 N1 C3 C4 30.71(10) . . . . ?
O2 C5 C10 O3 -178.99(11) . . . . ?
O2 C5 C10 O4 -2.08(13) . . . . ?
O2 C5 C13 O5 -151.89(11) . . . . ?
O2 C5 C13 O6 32.72(13) . . . . ?
O7 C19 C20 C21 178.80(11) . . . . ?
N1 O1 C1 C2 10.52(13) . . . . ?
N1 O1 C1 C6 -172.18(11) . . . . ?
N1 O2 C5 C4 -17.68(11) . . . . ?
N1 O2 C5 C10 -139.75(9) . . . . ?
N1 O2 C5 C13 105.08(10) . . . . ?
N1 C3 C4 C5 -39.76(10) . . . . ?
N1 C3 C4 C16 83.10(11) . . . . ?
C1 O1 N1 O2 91.50(9) . . . . ?
C1 O1 N1 C3 -17.25(11) . . . . ?
C1 C2 C3 Cl1 103.11(10) . . . . ?
C1 C2 C3 N1 -11.29(12) . . . . ?
C1 C2 C3 C4 -125.90(11) . . . . ?
C1 C2 C9 C8 -0.73(17) . . . . ?
C1 C6 C7 C8 -0.26(19) . . . . ?
C2 C1 C6 C7 -0.12(18) . . . . ?
C2 C3 C4 C5 74.05(11) . . . . ?
C2 C3 C4 C16 -163.09(10) . . . . ?
C3 C2 C9 C8 175.48(12) . . . . ?
C3 C4 C5 O2 34.86(10) . . . . ?
C3 C4 C5 C10 155.11(9) . . . . ?
C3 C4 C5 C13 -87.69(10) . . . . ?
C3 C4 C16 C17 -59.34(15) . . . . ?
C3 C4 C16 C21 119.66(12) . . . . ?
C4 C5 C10 O3 63.21(15) . . . . ?
C4 C5 C10 O4 -119.88(10) . . . . ?
C4 C5 C13 O5 -32.95(16) . . . . ?
C4 C5 C13 O6 151.66(10) . . . . ?
C4 C16 C17 C18 179.11(11) . . . . ?
C4 C16 C21 C20 -179.60(11) . . . . ?
C5 O2 N1 O1 -118.49(9) . . . . ?
C5 O2 N1 C3 -7.95(11) . . . . ?
C5 C4 C16 C17 54.47(15) . . . . ?
C5 C4 C16 C21 -126.53(11) . . . . ?
C6 C1 C2 C3 -176.40(11) . . . . ?
C6 C1 C2 C9 0.63(19) . . . . ?
C6 C7 C8 C9 0.14(19) . . . . ?
C7 C8 C9 C2 0.36(18) . . . . ?
C9 C2 C3 Cl1 -73.48(14) . . . . ?
C9 C2 C3 N1 172.12(12) . . . . ?
C9 C2 C3 C4 57.51(17) . . . . ?
C10 O4 C11 C12 -80.29(13) . . . . ?
C10 C5 C13 O5 89.35(13) . . . . ?
C10 C5 C13 O6 -86.04(11) . . . . ?
C11 O4 C10 O3 1.61(18) . . . . ?
C11 O4 C10 C5 -175.09(10) . . . . ?
C13 O6 C14 C15 88.48(15) . . . . ?
C13 C5 C10 O3 -58.83(14) . . . . ?
C13 C5 C10 O4 118.08(10) . . . . ?
C14 O6 C13 O5 -2.39(19) . . . . ?
C14 O6 C13 C5 172.80(10) . . . . ?
C16 C4 C5 O2 -88.47(11) . . . . ?
C16 C4 C5 C10 31.78(13) . . . . ?
C16 C4 C5 C13 148.98(10) . . . . ?
C16 C17 C18 C19 -0.07(18) . . . . ?
C17 C16 C21 C20 -0.55(18) . . . . ?
C17 C18 C19 O7 -179.20(11) . . . . ?
C17 C18 C19 C20 0.46(18) . . . . ?
C18 C19 C20 C21 -0.89(18) . . . . ?
C19 C20 C21 C16 0.94(18) . . . . ?
C21 C16 C17 C18 0.11(18) . . . . ?
C22 O7 C19 C18 -1.72(17) . . . . ?
C22 O7 C19 C20 178.60(11) . . . . ?

_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_AL272
_database_code_depnum_ccdc_archive 'CCDC 2237937'
loop_
_audit_author_name
_audit_author_address
'Yulia Nelyubina'
;AN Nesmeyanov Institute of Organoelement Compounds
Russia
;
_audit_update_record             
;
2023-01-25 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_audit_creation_date             2023-01-25
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H27 N O7'
_chemical_formula_sum            'C28 H27 N O7'
_chemical_formula_weight         489.50
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.0942(6)
_cell_length_b                   12.8516(4)
_cell_length_c                   20.5407(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.074(2)
_cell_angle_gamma                90
_cell_volume                     4769.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5635
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.71
_cell_measurement_theta_min      2.16
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0726 after correction.
The Ratio of minimum to maximum transmission is 0.7602.
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    1.363
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            31219
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         1.945
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest D8'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4584
_reflns_number_total             6335
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         6335
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+5.1159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1239
_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. Restrained distances
 O6-C14 \\sim O6-C14'
 with sigma of 0.02
 C15-C14 \\sim C15'-C14'
 with sigma of 0.02
 O6-C13 \\sim O6'-C13
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C14) = Uanis(C14')
Uanis(C15) = Uanis(C15')
Uanis(O6') = Uanis(O6)
4. Others
 Sof(O6')=Sof(C14')=Sof(H14A)=Sof(H14B)=Sof(C15')=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=1-FVAR(1)
 Sof(O6)=Sof(C14)=Sof(H14C)=Sof(H14D)=Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=
 FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14'(H14A,H14B), C14(H14C,H14D)
5.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C17(H17), C18(H18), C20(H20), C21(H21),
 C24(H24), C25(H25), C26(H26), C27(H27), C28(H28)
5.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C22(H22A,H22B,H22C), C15'(H15A,H15B,H15C), C15(H15D,H15E,
 H15F)
;
_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 -0.78916(6) -0.62803(9) -0.74099(5) 0.0192(3) Uani 1 1 d . . . . .
O2 O -0.72935(6) -0.77814(9) -0.70954(5) 0.0167(2) Uani 1 1 d . . . . .
O3 O -0.64109(7) -0.94251(9) -0.68344(6) 0.0231(3) Uani 1 1 d . . . . .
O4 O -0.70292(7) -0.97524(9) -0.59345(6) 0.0213(3) Uani 1 1 d . . . . .
O5 O -0.81584(6) -0.82800(9) -0.56083(6) 0.0189(3) Uani 1 1 d . . . . .
O7 O -0.37491(6) -0.80259(10) -0.59366(6) 0.0217(3) Uani 1 1 d . . . . .
N1 N -0.71911(7) -0.66528(10) -0.71243(7) 0.0157(3) Uani 1 1 d . . . . .
C1 C -0.83397(9) -0.60531(13) -0.69023(8) 0.0177(3) Uani 1 1 d . . . . .
C2 C -0.79594(9) -0.60671(12) -0.63058(8) 0.0154(3) Uani 1 1 d . . . . .
C3 C -0.71527(8) -0.63048(12) -0.64160(7) 0.0139(3) Uani 1 1 d . . . . .
C4 C -0.68414(8) -0.72661(12) -0.60449(8) 0.0133(3) Uani 1 1 d . . . . .
H4 H -0.7006 -0.7257 -0.5588 0.016 Uiso 1 1 calc R U . . .
C5 C -0.72582(9) -0.81322(12) -0.64358(7) 0.0142(3) Uani 1 1 d . . . . .
C6 C -0.90803(9) -0.57980(14) -0.69863(9) 0.0219(4) Uani 1 1 d . . . . .
H6 H -0.9331 -0.5796 -0.7405 0.026 Uiso 1 1 calc R U . . .
C7 C -0.94383(10) -0.55446(14) -0.64253(9) 0.0243(4) Uani 1 1 d . . . . .
H7 H -0.9948 -0.5361 -0.6459 0.029 Uiso 1 1 calc R U . . .
C8 C -0.90650(10) -0.55547(13) -0.58158(9) 0.0222(4) Uani 1 1 d . . . . .
H8 H -0.9324 -0.5380 -0.5440 0.027 Uiso 1 1 calc R U . . .
C9 C -0.83185(9) -0.58169(13) -0.57465(8) 0.0178(3) Uani 1 1 d . . . . .
H9 H -0.8063 -0.5824 -0.5330 0.021 Uiso 1 1 calc R U . . .
C10 C -0.68356(9) -0.91774(13) -0.64386(8) 0.0159(3) Uani 1 1 d . . . . .
C11 C -0.67222(10) -1.08030(13) -0.58916(9) 0.0237(4) Uani 1 1 d . . . . .
H11A H -0.6202 -1.0782 -0.5717 0.028 Uiso 1 1 calc R U . . .
H11B H -0.6737 -1.1132 -0.6328 0.028 Uiso 1 1 calc R U . . .
C12 C -0.71905(10) -1.14054(14) -0.54423(9) 0.0252(4) Uani 1 1 d . . . . .
H12A H -0.7171 -1.1071 -0.5013 0.038 Uiso 1 1 calc R U . . .
H12B H -0.7003 -1.2119 -0.5399 0.038 Uiso 1 1 calc R U . . .
H12C H -0.7703 -1.1420 -0.5621 0.038 Uiso 1 1 calc R U . . .
C13 C -0.80269(9) -0.83414(12) -0.61761(8) 0.0160(3) Uani 1 1 d D . . . .
C16 C -0.60090(9) -0.73974(12) -0.60359(8) 0.0143(3) Uani 1 1 d . . . . .
C17 C -0.56159(9) -0.73420(13) -0.65982(8) 0.0184(3) Uani 1 1 d . . . . .
H17 H -0.5868 -0.7154 -0.6999 0.022 Uiso 1 1 calc R U . . .
C18 C -0.48642(9) -0.75546(14) -0.65880(8) 0.0190(3) Uani 1 1 d . . . . .
H18 H -0.4608 -0.7521 -0.6979 0.023 Uiso 1 1 calc R U . . .
C19 C -0.44878(9) -0.78170(13) -0.60050(8) 0.0170(3) Uani 1 1 d . . . . .
C20 C -0.48727(9) -0.78694(13) -0.54378(8) 0.0182(3) Uani 1 1 d . . . . .
H20 H -0.4619 -0.8051 -0.5037 0.022 Uiso 1 1 calc R U . . .
C21 C -0.56234(9) -0.76581(13) -0.54543(8) 0.0162(3) Uani 1 1 d . . . . .
H21 H -0.5879 -0.7691 -0.5063 0.019 Uiso 1 1 calc R U . . .
C22 C -0.33503(10) -0.80702(15) -0.65198(9) 0.0256(4) Uani 1 1 d . . . . .
H22A H -0.2838 -0.8279 -0.6411 0.038 Uiso 1 1 calc R U . . .
H22B H -0.3356 -0.7383 -0.6727 0.038 Uiso 1 1 calc R U . . .
H22C H -0.3585 -0.8579 -0.6821 0.038 Uiso 1 1 calc R U . . .
C23 C -0.67022(9) -0.53139(12) -0.63305(8) 0.0161(3) Uani 1 1 d . . . . .
C24 C -0.64144(9) -0.50426(13) -0.57117(8) 0.0199(3) Uani 1 1 d . . . . .
H24 H -0.6461 -0.5508 -0.5357 0.024 Uiso 1 1 calc R U . . .
C25 C -0.60592(10) -0.40925(14) -0.56105(9) 0.0220(4) Uani 1 1 d . . . . .
H25 H -0.5861 -0.3912 -0.5188 0.026 Uiso 1 1 calc R U . . .
C26 C -0.59943(9) -0.34070(13) -0.61278(9) 0.0206(4) Uani 1 1 d . . . . .
H26 H -0.5751 -0.2758 -0.6059 0.025 Uiso 1 1 calc R U . . .
C27 C -0.62836(9) -0.36672(14) -0.67411(9) 0.0211(4) Uani 1 1 d . . . . .
H27 H -0.6243 -0.3195 -0.7093 0.025 Uiso 1 1 calc R U . . .
C28 C -0.66350(9) -0.46205(13) -0.68452(8) 0.0183(3) Uani 1 1 d . . . . .
H28 H -0.6830 -0.4799 -0.7269 0.022 Uiso 1 1 calc R U . . .
O6' O -0.8458(13) -0.8911(17) -0.6579(11) 0.0196(4) Uani 0.082(5) 1 d D . P A 1
C14' C -0.9150(13) -0.921(2) -0.6394(14) 0.0261(5) Uani 0.082(5) 1 d D . P A 1
H14A H -0.9458 -0.8578 -0.6358 0.031 Uiso 0.082(5) 1 calc R U P A 1
H14B H -0.9095 -0.9527 -0.5955 0.031 Uiso 0.082(5) 1 calc R U P A 1
C15' C -0.9548(16) -0.995(2) -0.6837(18) 0.0475(9) Uani 0.082(5) 1 d D . P A 1
H15A H -0.9235 -1.0559 -0.6904 0.071 Uiso 0.082(5) 1 calc R U P A 1
H15B H -0.9668 -0.9613 -0.7257 0.071 Uiso 0.082(5) 1 calc R U P A 1
H15C H -1.0006 -1.0173 -0.6644 0.071 Uiso 0.082(5) 1 calc R U P A 1
O6 O -0.85027(10) -0.86111(15) -0.66624(9) 0.0196(4) Uani 0.918(5) 1 d D . P A
2
C14 C -0.92527(11) -0.8872(2) -0.64860(13) 0.0261(5) Uani 0.918(5) 1 d D . P A
2
H14C H -0.9612 -0.8675 -0.6845 0.031 Uiso 0.918(5) 1 calc R U P A 2
H14D H -0.9376 -0.8480 -0.6091 0.031 Uiso 0.918(5) 1 calc R U P A 2
C15 C -0.93038(15) -1.00189(19) -0.63578(17) 0.0475(9) Uani 0.918(5) 1 d D U P
A 2
H15D H -0.8978 -1.0200 -0.5978 0.071 Uiso 0.918(5) 1 calc R U P A 2
H15E H -0.9151 -1.0404 -0.6739 0.071 Uiso 0.918(5) 1 calc R U P A 2
H15F H -0.9816 -1.0201 -0.6272 0.071 Uiso 0.918(5) 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
O1 N1 1.4492(17) . ?
O1 C1 1.3859(19) . ?
O2 N1 1.4639(17) . ?
O2 C5 1.4262(19) . ?
O3 C10 1.1917(19) . ?
O4 C10 1.3340(19) . ?
O4 C11 1.461(2) . ?
O5 C13 1.2053(19) . ?
O7 C19 1.3633(19) . ?
O7 C22 1.432(2) . ?
N1 C3 1.520(2) . ?
C1 C2 1.373(2) . ?
C1 C6 1.381(2) . ?
C2 C3 1.520(2) . ?
C2 C9 1.388(2) . ?
C3 C4 1.542(2) . ?
C3 C23 1.517(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.545(2) . ?
C4 C16 1.515(2) . ?
C5 C10 1.546(2) . ?
C5 C13 1.540(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.391(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.501(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O6' 1.327(16) . ?
C13 O6 1.329(2) . ?
C16 C17 1.390(2) . ?
C16 C21 1.392(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(2) . ?
C19 C20 1.391(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.392(2) . ?
C23 C28 1.393(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.390(2) . ?
C26 H26 0.9500 . ?
C26 C27 1.379(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.392(2) . ?
C28 H28 0.9500 . ?
O6' C14' 1.38(3) . ?
C14' H14A 0.9900 . ?
C14' H14B 0.9900 . ?
C14' C15' 1.478(19) . ?
C15' H15A 0.9800 . ?
C15' H15B 0.9800 . ?
C15' H15C 0.9800 . ?
O6 C14 1.462(3) . ?
C14 H14C 0.9900 . ?
C14 H14D 0.9900 . ?
C14 C15 1.500(4) . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 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 O1 N1 107.42(12) . . ?
C5 O2 N1 110.63(11) . . ?
C10 O4 C11 116.36(13) . . ?
C19 O7 C22 117.17(14) . . ?
O1 N1 O2 103.52(11) . . ?
O1 N1 C3 106.52(11) . . ?
O2 N1 C3 104.60(11) . . ?
C2 C1 O1 112.54(14) . . ?
C2 C1 C6 123.44(16) . . ?
C6 C1 O1 123.97(16) . . ?
C1 C2 C3 108.01(13) . . ?
C1 C2 C9 120.09(15) . . ?
C9 C2 C3 131.74(15) . . ?
N1 C3 C4 103.54(12) . . ?
C2 C3 N1 101.92(12) . . ?
C2 C3 C4 114.56(12) . . ?
C23 C3 N1 110.76(12) . . ?
C23 C3 C2 109.17(13) . . ?
C23 C3 C4 115.82(13) . . ?
C3 C4 H4 109.6 . . ?
C3 C4 C5 99.50(12) . . ?
C5 C4 H4 109.6 . . ?
C16 C4 C3 115.58(13) . . ?
C16 C4 H4 109.6 . . ?
C16 C4 C5 112.55(12) . . ?
O2 C5 C4 105.17(12) . . ?
O2 C5 C10 105.55(12) . . ?
O2 C5 C13 112.89(13) . . ?
C4 C5 C10 113.58(13) . . ?
C13 C5 C4 111.76(12) . . ?
C13 C5 C10 107.80(13) . . ?
C1 C6 H6 121.8 . . ?
C1 C6 C7 116.36(17) . . ?
C7 C6 H6 121.8 . . ?
C6 C7 H7 119.4 . . ?
C8 C7 C6 121.23(16) . . ?
C8 C7 H7 119.4 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.09(16) . . ?
C9 C8 H8 119.5 . . ?
C2 C9 C8 117.79(16) . . ?
C2 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
O3 C10 O4 125.97(15) . . ?
O3 C10 C5 124.88(15) . . ?
O4 C10 C5 109.14(13) . . ?
O4 C11 H11A 110.4 . . ?
O4 C11 H11B 110.4 . . ?
O4 C11 C12 106.76(14) . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 C5 123.54(15) . . ?
O5 C13 O6' 119.9(12) . . ?
O5 C13 O6 126.21(16) . . ?
O6' C13 C5 113.1(12) . . ?
O6 C13 C5 110.24(15) . . ?
C17 C16 C4 122.47(15) . . ?
C17 C16 C21 118.05(15) . . ?
C21 C16 C4 119.31(14) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.51(16) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 120.1 . . ?
C17 C18 C19 119.79(15) . . ?
C19 C18 H18 120.1 . . ?
O7 C19 C18 124.77(15) . . ?
O7 C19 C20 115.87(15) . . ?
C18 C19 C20 119.36(15) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.33(16) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 H21 119.5 . . ?
C20 C21 C16 120.96(15) . . ?
C20 C21 H21 119.5 . . ?
O7 C22 H22A 109.5 . . ?
O7 C22 H22B 109.5 . . ?
O7 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C3 119.23(14) . . ?
C24 C23 C28 119.29(15) . . ?
C28 C23 C3 121.15(15) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.25(16) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 119.98(16) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.07(16) . . ?
C27 C26 H26 120.0 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.11(16) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.29(16) . . ?
C27 C28 H28 119.9 . . ?
C13 O6' C14' 120(2) . . ?
O6' C14' H14A 108.4 . . ?
O6' C14' H14B 108.4 . . ?
O6' C14' C15' 115(2) . . ?
H14A C14' H14B 107.5 . . ?
C15' C14' H14A 108.4 . . ?
C15' C14' H14B 108.4 . . ?
C14' C15' H15A 109.5 . . ?
C14' C15' H15B 109.5 . . ?
C14' C15' H15C 109.5 . . ?
H15A C15' H15B 109.5 . . ?
H15A C15' H15C 109.5 . . ?
H15B C15' H15C 109.5 . . ?
C13 O6 C14 116.49(17) . . ?
O6 C14 H14C 109.7 . . ?
O6 C14 H14D 109.7 . . ?
O6 C14 C15 109.62(17) . . ?
H14C C14 H14D 108.2 . . ?
C15 C14 H14C 109.7 . . ?
C15 C14 H14D 109.7 . . ?
C14 C15 H15D 109.5 . . ?
C14 C15 H15E 109.5 . . ?
C14 C15 H15F 109.5 . . ?
H15D C15 H15E 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 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 N1 C3 C2 18.24(14) . . . . ?
O1 N1 C3 C4 137.43(12) . . . . ?
O1 N1 C3 C23 -97.79(14) . . . . ?
O1 C1 C2 C3 1.56(19) . . . . ?
O1 C1 C2 C9 177.52(14) . . . . ?
O1 C1 C6 C7 -177.05(16) . . . . ?
O2 N1 C3 C2 -90.99(13) . . . . ?
O2 N1 C3 C4 28.20(14) . . . . ?
O2 N1 C3 C23 152.98(12) . . . . ?
O2 C5 C10 O3 24.4(2) . . . . ?
O2 C5 C10 O4 -154.92(13) . . . . ?
O2 C5 C13 O5 -152.74(15) . . . . ?
O2 C5 C13 O6' 48.1(12) . . . . ?
O2 C5 C13 O6 28.40(19) . . . . ?
O5 C13 O6' C14' 16(3) . . . . ?
O5 C13 O6 C14 -1.0(3) . . . . ?
O7 C19 C20 C21 179.21(15) . . . . ?
N1 O1 C1 C2 10.69(18) . . . . ?
N1 O1 C1 C6 -171.83(15) . . . . ?
N1 O2 C5 C4 -20.82(15) . . . . ?
N1 O2 C5 C10 -141.20(12) . . . . ?
N1 O2 C5 C13 101.28(14) . . . . ?
N1 C3 C4 C5 -39.12(13) . . . . ?
N1 C3 C4 C16 81.62(15) . . . . ?
N1 C3 C23 C24 -160.73(14) . . . . ?
N1 C3 C23 C28 25.8(2) . . . . ?
C1 O1 N1 O2 91.72(13) . . . . ?
C1 O1 N1 C3 -18.27(15) . . . . ?
C1 C2 C3 N1 -12.27(16) . . . . ?
C1 C2 C3 C4 -123.34(15) . . . . ?
C1 C2 C3 C23 104.92(15) . . . . ?
C1 C2 C9 C8 -0.1(2) . . . . ?
C1 C6 C7 C8 -0.2(3) . . . . ?
C2 C1 C6 C7 0.2(3) . . . . ?
C2 C3 C4 C5 70.98(15) . . . . ?
C2 C3 C4 C16 -168.28(13) . . . . ?
C2 C3 C23 C24 87.82(18) . . . . ?
C2 C3 C23 C28 -85.61(18) . . . . ?
C3 C2 C9 C8 174.73(16) . . . . ?
C3 C4 C5 O2 36.77(14) . . . . ?
C3 C4 C5 C10 151.70(12) . . . . ?
C3 C4 C5 C13 -86.06(14) . . . . ?
C3 C4 C16 C17 -49.5(2) . . . . ?
C3 C4 C16 C21 135.27(15) . . . . ?
C3 C23 C24 C25 -174.02(15) . . . . ?
C3 C23 C28 C27 173.45(15) . . . . ?
C4 C3 C23 C24 -43.2(2) . . . . ?
C4 C3 C23 C28 143.32(15) . . . . ?
C4 C5 C10 O3 -90.3(2) . . . . ?
C4 C5 C10 O4 90.38(15) . . . . ?
C4 C5 C13 O5 -34.4(2) . . . . ?
C4 C5 C13 O6' 166.5(12) . . . . ?
C4 C5 C13 O6 146.73(15) . . . . ?
C4 C16 C17 C18 -174.25(15) . . . . ?
C4 C16 C21 C20 174.57(15) . . . . ?
C5 O2 N1 O1 -116.09(12) . . . . ?
C5 O2 N1 C3 -4.69(14) . . . . ?
C5 C4 C16 C17 63.8(2) . . . . ?
C5 C4 C16 C21 -111.35(16) . . . . ?
C5 C13 O6' C14' 176.4(19) . . . . ?
C5 C13 O6 C14 177.81(15) . . . . ?
C6 C1 C2 C3 -175.94(16) . . . . ?
C6 C1 C2 C9 0.0(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C2 0.0(2) . . . . ?
C9 C2 C3 N1 172.42(16) . . . . ?
C9 C2 C3 C4 61.3(2) . . . . ?
C9 C2 C3 C23 -70.4(2) . . . . ?
C10 O4 C11 C12 -161.84(15) . . . . ?
C10 C5 C13 O5 91.07(18) . . . . ?
C10 C5 C13 O6' -68.0(12) . . . . ?
C10 C5 C13 O6 -87.78(17) . . . . ?
C11 O4 C10 O3 -3.8(2) . . . . ?
C11 O4 C10 C5 175.51(14) . . . . ?
C13 C5 C10 O3 145.33(16) . . . . ?
C13 C5 C10 O4 -34.02(17) . . . . ?
C13 O6' C14' C15' -172(3) . . . . ?
C13 O6 C14 C15 -91.2(3) . . . . ?
C16 C4 C5 O2 -86.15(15) . . . . ?
C16 C4 C5 C10 28.78(18) . . . . ?
C16 C4 C5 C13 151.01(13) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C17 C16 C21 C20 -0.8(2) . . . . ?
C17 C18 C19 O7 -179.00(16) . . . . ?
C17 C18 C19 C20 0.4(3) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C21 C16 C17 C18 1.0(2) . . . . ?
C22 O7 C19 C18 -6.0(2) . . . . ?
C22 O7 C19 C20 174.54(15) . . . . ?
C23 C3 C4 C5 -160.56(13) . . . . ?
C23 C3 C4 C16 -39.82(19) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C23 C28 C27 0.0(2) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C28 -0.6(3) . . . . ?
C26 C27 C28 C23 0.5(3) . . . . ?
C28 C23 C24 C25 -0.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
