# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_GS409
_database_code_depnum_ccdc_archive 'CCDC 2346928'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2020-05-23

_chemical_formula_moiety         'C22 H27 N O4'
_chemical_formula_sum            'C22 H27 N O4'
_chemical_formula_weight         369.464
_chemical_absolute_configuration rmad
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           ' P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2

_symmetry_Int_Tables_number      19
_cell_length_a                   6.06579(5)
_cell_length_b                   16.68048(13)
_cell_length_c                   18.97466(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1919.86(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(2)
_cell_measurement_reflns_used    3018
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_F_000             792
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.9995
_diffrn_reflns_Laue_measured_fraction_max 0.9903
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12058
_diffrn_reflns_point_group_measured_fraction_full 0.9836
_diffrn_reflns_point_group_measured_fraction_max 0.9556
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         77.39
_diffrn_reflns_theta_min         3.53
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9903
_exptl_absorpt_coefficient_mu    0.705
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_correction_T_min  0.8947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.0(2)
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.908
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              21
_reflns_limit_k_min              -20
_reflns_limit_l_max              24
_reflns_limit_l_min              -23
_reflns_number_gt                3778
_reflns_number_total             3897
_reflns_threshold_expression     I>=2u(I)
_refine_diff_density_max         0.1623
_refine_diff_density_min         -0.1708
_refine_diff_density_rms         0.0406
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_d_res_high            0.7900
_refine_ls_d_res_low             12.5279
_refine_ls_goodness_of_fit_ref   1.0578
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    43
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3897
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.0578
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²+0.2621P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0814
_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:
 C2(H2), C7(H7), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C12(H12a,H12b), C9(H9a,H9b), C4(H4a,H4b), C11(H11a,H11b),
 C5(H5a,H5b), C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C23(H23), C21(H21)
2.d Idealised Me refined as rotating group:
 C14(H14a,H14b,H14c), C15(H15a,H15b,H15c)
;
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_refinement_flags_posn
O16 O 0.31599(15) 0.45539(5) 0.57861(6) 0.0316(2) Uani 1.000000 .
O18 O 0.64953(17) 0.41580(6) 0.54039(6) 0.0380(3) Uani 1.000000 .
O27 O -0.0049(2) 0.06961(7) 0.63524(8) 0.0570(4) Uani 1.000000 .
N25 N 0.1893(2) 0.08097(7) 0.62144(7) 0.0378(3) Uani 1.000000 .
O26 O 0.3290(2) 0.02878(6) 0.61994(8) 0.0567(3) Uani 1.000000 .
C2 C 0.31395(19) 0.74209(6) 0.62071(6) 0.0205(2) Uani 1.000000 .
H2 H 0.47280(19) 0.74037(6) 0.61141(6) 0.0245(3) Uiso 1.000000 R
C10 C -0.0354(2) 0.65457(7) 0.59748(7) 0.0245(2) Uani 1.000000 .
H10a H -0.1201(2) 0.64265(7) 0.55540(7) 0.0293(3) Uiso 1.000000 R
H10b H -0.1076(2) 0.69558(7) 0.62542(7) 0.0293(3) Uiso 1.000000 R
C17 C 0.4686(2) 0.40107(7) 0.56344(6) 0.0226(2) Uani 1.000000 .
C12 C 0.2466(2) 0.83153(7) 0.62433(6) 0.0231(2) Uani 1.000000 .
H12a H 0.3320(2) 0.86623(7) 0.59371(6) 0.0277(3) Uiso 1.000000 R
H12b H 0.0897(2) 0.84079(7) 0.61863(6) 0.0277(3) Uiso 1.000000 R
C13 C 0.3258(2) 0.83138(7) 0.70293(6) 0.0240(2) Uani 1.000000 .
C19 C 0.3891(2) 0.31780(7) 0.57856(6) 0.0219(2) Uani 1.000000 .
C9 C 0.2777(2) 0.65962(7) 0.50537(6) 0.0268(3) Uani 1.000000 .
H9a H 0.1750(2) 0.68608(7) 0.47385(6) 0.0322(3) Uiso 1.000000 R
H9b H 0.4249(2) 0.67999(7) 0.49646(6) 0.0322(3) Uiso 1.000000 R
C22 C 0.2591(2) 0.16394(7) 0.60581(7) 0.0273(3) Uani 1.000000 .
C24 C 0.1797(2) 0.30364(7) 0.60586(7) 0.0251(2) Uani 1.000000 .
H24 H 0.0846(2) 0.34622(7) 0.61467(7) 0.0302(3) Uiso 1.000000 R
C4 C 0.4095(2) 0.67090(9) 0.73641(7) 0.0335(3) Uani 1.000000 .
H4a H 0.5537(2) 0.69003(9) 0.75075(7) 0.0402(4) Uiso 1.000000 R
H4b H 0.3308(2) 0.65391(9) 0.77831(7) 0.0402(4) Uiso 1.000000 R
C6 C 0.27660(19) 0.59252(7) 0.62327(7) 0.0225(2) Uani 1.000000 .
C20 C 0.5323(2) 0.25447(7) 0.56499(6) 0.0252(2) Uani 1.000000 .
H20 H 0.6720(2) 0.26468(7) 0.54688(6) 0.0302(3) Uiso 1.000000 R
C7 C 0.3682(2) 0.53915(7) 0.56481(7) 0.0269(3) Uani 1.000000 .
H7 H 0.5287(2) 0.54547(7) 0.56290(7) 0.0323(3) Uiso 1.000000 R
C3 C 0.2836(2) 0.73854(7) 0.70079(6) 0.0235(2) Uani 1.000000 .
H3 H 0.1264(2) 0.72986(7) 0.71000(6) 0.0282(3) Uiso 1.000000 R
C23 C 0.1135(2) 0.22556(7) 0.61986(7) 0.0272(3) Uani 1.000000 .
H23 H -0.0256(2) 0.21501(7) 0.63827(7) 0.0327(3) Uiso 1.000000 R
C11 C 0.0289(2) 0.57902(7) 0.64044(7) 0.0273(3) Uani 1.000000 .
H11a H -0.0050(2) 0.58334(7) 0.69025(7) 0.0328(3) Uiso 1.000000 R
H11b H -0.0298(2) 0.52963(7) 0.62105(7) 0.0328(3) Uiso 1.000000 R
C1 C 0.21185(19) 0.67258(7) 0.58243(6) 0.0207(2) Uani 1.000000 .
C5 C 0.4366(2) 0.59878(8) 0.68579(8) 0.0303(3) Uani 1.000000 .
H5a H 0.5854(2) 0.60018(8) 0.66709(8) 0.0364(3) Uiso 1.000000 R
H5b H 0.4233(2) 0.55007(8) 0.71339(8) 0.0364(3) Uiso 1.000000 R
C14 C 0.1906(2) 0.87988(9) 0.75480(7) 0.0321(3) Uani 1.000000 .
H14a H 0.2092(16) 0.93597(9) 0.7452(4) 0.0481(4) Uiso 1.000000 GR
H14b H 0.0378(3) 0.8659(5) 0.7502(4) 0.0481(4) Uiso 1.000000 GR
H14c H 0.2392(14) 0.8685(6) 0.80190(8) 0.0481(4) Uiso 1.000000 GR
C21 C 0.4675(2) 0.17625(7) 0.57839(7) 0.0280(3) Uani 1.000000 .
H21 H 0.5613(2) 0.13340(7) 0.56924(7) 0.0336(3) Uiso 1.000000 R
C8 C 0.2694(3) 0.56804(7) 0.49569(7) 0.0316(3) Uani 1.000000 .
H8a H 0.1192(3) 0.54918(7) 0.48984(7) 0.0379(3) Uiso 1.000000 R
H8b H 0.3572(3) 0.55100(7) 0.45566(7) 0.0379(3) Uiso 1.000000 R
C15 C 0.5689(2) 0.85355(8) 0.70931(7) 0.0310(3) Uani 1.000000 .
H15a H 0.6534(3) 0.8223(5) 0.6765(5) 0.0465(4) Uiso 1.000000 GR
H15b H 0.5875(3) 0.90949(18) 0.6990(6) 0.0465(4) Uiso 1.000000 GR
H15c H 0.6188(6) 0.8428(7) 0.75638(19) 0.0465(4) Uiso 1.000000 GR


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
O16 C17 1.3270(15) . ?
O16 C7 1.4565(13) . ?
O18 C17 1.2066(16) . ?
O27 N25 1.2220(19) . ?
N25 O26 1.2152(18) . ?
N25 C22 1.4772(16) . ?
C2 H2 0.9800 . ?
C2 C12 1.5484(15) . ?
C2 C3 1.5317(16) . ?
C2 C1 1.5017(15) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 C11 1.5508(16) . ?
C10 C1 1.5559(16) . ?
C17 C19 1.4981(16) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 C13 1.5668(16) . ?
C13 C3 1.5701(16) . ?
C13 C14 1.5151(17) . ?
C13 C15 1.5252(17) . ?
C19 C24 1.3918(17) . ?
C19 C20 1.3920(17) . ?
C9 H9a 0.9700 . ?
C9 H9b 0.9700 . ?
C9 C1 1.5313(16) . ?
C9 C8 1.5394(17) . ?
C22 C23 1.3809(19) . ?
C22 C21 1.383(2) . ?
C24 H24 0.9300 . ?
C24 C23 1.3884(17) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C4 C3 1.5210(18) . ?
C4 C5 1.548(2) . ?
C6 C7 1.5270(17) . ?
C6 C11 1.5540(17) . ?
C6 C1 1.5932(15) . ?
C6 C5 1.5364(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3862(18) . ?
C7 H7 0.9800 . ?
C7 C8 1.5203(19) . ?
C3 H3 0.9800 . ?
C23 H23 0.9300 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C21 H21 0.9300 . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O16 C17 117.66(10) . . ?
O26 N25 O27 124.49(12) . . ?
C22 N25 O27 117.67(12) . . ?
C22 N25 O26 117.84(13) . . ?
C12 C2 H2 107.20(6) . . ?
C3 C2 H2 107.20(6) . . ?
C3 C2 C12 87.79(8) . . ?
C1 C2 H2 107.20(6) . . ?
C1 C2 C12 131.03(10) . . ?
C1 C2 C3 113.60(9) . . ?
H10b C10 H10a 110.8 . . ?
C11 C10 H10a 113.53(7) . . ?
C11 C10 H10b 113.53(7) . . ?
C1 C10 H10a 113.53(6) . . ?
C1 C10 H10b 113.53(6) . . ?
C1 C10 C11 90.64(9) . . ?
O18 C17 O16 125.04(11) . . ?
C19 C17 O16 111.51(10) . . ?
C19 C17 O18 123.45(11) . . ?
H12a C12 C2 114.04(6) . . ?
H12b C12 C2 114.04(6) . . ?
H12b C12 H12a 111.2 . . ?
C13 C12 C2 87.69(8) . . ?
C13 C12 H12a 114.04(6) . . ?
C13 C12 H12b 114.04(6) . . ?
C3 C13 C12 85.81(8) . . ?
C14 C13 C12 116.83(10) . . ?
C14 C13 C3 117.07(10) . . ?
C15 C13 C12 111.82(10) . . ?
C15 C13 C3 113.51(10) . . ?
C15 C13 C14 110.02(10) . . ?
C24 C19 C17 121.51(11) . . ?
C20 C19 C17 117.84(11) . . ?
C20 C19 C24 120.65(11) . . ?
H9b C9 H9a 108.9 . . ?
C1 C9 H9a 110.91(7) . . ?
C1 C9 H9b 110.91(7) . . ?
C8 C9 H9a 110.91(8) . . ?
C8 C9 H9b 110.91(8) . . ?
C8 C9 C1 104.21(10) . . ?
C23 C22 N25 118.40(12) . . ?
C21 C22 N25 118.46(12) . . ?
C21 C22 C23 123.14(11) . . ?
H24 C24 C19 120.19(7) . . ?
C23 C24 C19 119.62(11) . . ?
C23 C24 H24 120.19(8) . . ?
H4b C4 H4a 108.1 . . ?
C3 C4 H4a 109.50(7) . . ?
C3 C4 H4b 109.50(7) . . ?
C5 C4 H4a 109.50(7) . . ?
C5 C4 H4b 109.50(7) . . ?
C5 C4 C3 110.74(11) . . ?
C11 C6 C7 114.82(10) . . ?
C1 C6 C7 103.00(10) . . ?
C1 C6 C11 89.15(8) . . ?
C5 C6 C7 111.75(10) . . ?
C5 C6 C11 117.32(11) . . ?
C5 C6 C1 118.31(10) . . ?
H20 C20 C19 119.89(7) . . ?
C21 C20 C19 120.22(12) . . ?
C21 C20 H20 119.89(8) . . ?
C6 C7 O16 110.45(10) . . ?
H7 C7 O16 109.01(6) . . ?
H7 C7 C6 109.01(6) . . ?
C8 C7 O16 111.93(11) . . ?
C8 C7 C6 107.36(10) . . ?
C8 C7 H7 109.01(7) . . ?
C13 C3 C2 88.16(8) . . ?
C4 C3 C2 114.14(10) . . ?
C4 C3 C13 129.65(11) . . ?
H3 C3 C2 107.44(6) . . ?
H3 C3 C13 107.44(6) . . ?
H3 C3 C4 107.44(7) . . ?
C24 C23 C22 118.46(12) . . ?
H23 C23 C22 120.77(8) . . ?
H23 C23 C24 120.77(8) . . ?
C6 C11 C10 90.86(9) . . ?
H11a C11 C10 113.49(7) . . ?
H11a C11 C6 113.49(7) . . ?
H11b C11 C10 113.49(7) . . ?
H11b C11 C6 113.49(7) . . ?
H11b C11 H11a 110.8 . . ?
C10 C1 C2 117.25(10) . . ?
C9 C1 C2 117.60(10) . . ?
C9 C1 C10 113.54(10) . . ?
C6 C1 C2 108.08(9) . . ?
C6 C1 C10 89.23(8) . . ?
C6 C1 C9 106.37(9) . . ?
C6 C5 C4 117.68(11) . . ?
H5a C5 C4 107.88(8) . . ?
H5a C5 C6 107.88(7) . . ?
H5b C5 C4 107.88(7) . . ?
H5b C5 C6 107.88(7) . . ?
H5b C5 H5a 107.2 . . ?
H14a C14 C13 109.5 . . ?
H14b C14 C13 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C13 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C20 C21 C22 117.92(11) . . ?
H21 C21 C22 121.04(7) . . ?
H21 C21 C20 121.04(8) . . ?
C7 C8 C9 101.46(10) . . ?
H8a C8 C9 111.48(8) . . ?
H8a C8 C7 111.48(7) . . ?
H8b C8 C9 111.48(7) . . ?
H8b C8 C7 111.48(7) . . ?
H8b C8 H8a 109.3 . . ?
H15a C15 C13 109.5 . . ?
H15b C15 C13 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C13 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 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
O16 C17 C19 C24 -0.63(13) . . . . ?
O16 C17 C19 C20 179.90(10) . . . . ?
O16 C7 C6 C11 -51.13(12) . . . . ?
O16 C7 C6 C1 -146.29(10) . . . . ?
O16 C7 C6 C5 85.67(11) . . . . ?
O16 C7 C8 C9 161.75(11) . . . . ?
O18 C17 C19 C24 179.30(13) . . . . ?
O18 C17 C19 C20 -0.17(15) . . . . ?
O27 N25 C22 C23 11.55(17) . . . . ?
O27 N25 C22 C21 -169.01(14) . . . . ?
N25 C22 C23 C24 179.35(12) . . . . ?
N25 C22 C21 C20 -178.99(12) . . . . ?
C2 C12 C13 C3 -23.87(9) . . . . ?
C2 C12 C13 C14 -142.18(8) . . . . ?
C2 C12 C13 C15 89.81(9) . . . . ?
C2 C3 C13 C12 24.14(9) . . . . ?
C2 C3 C13 C14 142.22(9) . . . . ?
C2 C3 C13 C15 -87.86(9) . . . . ?
C2 C3 C4 C5 -29.47(11) . . . . ?
C2 C1 C10 C11 -107.30(11) . . . . ?
C2 C1 C9 C8 147.38(12) . . . . ?
C2 C1 C6 C7 -128.89(10) . . . . ?
C2 C1 C6 C11 115.81(11) . . . . ?
C2 C1 C6 C5 -5.08(11) . . . . ?
C10 C11 C6 C7 -101.24(9) . . . . ?
C10 C11 C6 C1 2.71(9) . . . . ?
C10 C11 C6 C5 124.45(9) . . . . ?
C10 C1 C9 C8 -70.32(11) . . . . ?
C10 C1 C6 C7 112.61(9) . . . . ?
C10 C1 C6 C11 -2.70(10) . . . . ?
C10 C1 C6 C5 -123.58(9) . . . . ?
C17 C19 C24 C23 -179.26(11) . . . . ?
C17 C19 C20 C21 179.65(11) . . . . ?
C12 C13 C3 C4 144.46(9) . . . . ?
C13 C3 C4 C5 -138.48(14) . . . . ?
C19 C24 C23 C22 -0.25(13) . . . . ?
C19 C20 C21 C22 -0.47(14) . . . . ?
C9 C1 C6 C7 -1.74(10) . . . . ?
C9 C1 C6 C11 -117.04(11) . . . . ?
C9 C1 C6 C5 122.07(10) . . . . ?
C9 C8 C7 C6 40.39(11) . . . . ?
C4 C5 C6 C7 159.45(11) . . . . ?
C4 C5 C6 C11 -64.92(13) . . . . ?
C4 C5 C6 C1 40.10(13) . . . . ?


####################################################################### 
# 
# 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_gs713
_database_code_depnum_ccdc_archive 'CCDC 2346931'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C15 H24 O'
_chemical_formula_sum            'C15 H24 O'
_chemical_formula_weight         220.34

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

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   'P 32 '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   13.0367(2)
_cell_length_b                   13.0367(2)
_cell_length_c                   6.6998(1)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     986.11(3)
_cell_formula_units_Z            3
_cell_measurement_temperature    160.0(2)
_cell_measurement_reflns_used    2007
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      75.0

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.113
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366
_exptl_absorpt_coefficient_mu    0.508
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      160.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_reflns_number            9553
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         3.92
_diffrn_reflns_theta_max         80.34
_reflns_number_total             1421
_reflns_number_gt                1408
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXT (Sheldrick, 2015)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0505P)²+0.1231P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0120(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_number_reflns         1421
_refine_ls_number_parameters     152
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0812
_refine_ls_wR_factor_gt          0.0810
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.005

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66121(14) 0.68796(14) 0.5491(3) 0.0252(3) Uani 1 1 d . . .
H1 H 0.6108 0.6901 0.4384 0.030 Uiso 1 1 calc R . .
C2 C 0.61385(17) 0.70570(17) 0.7459(3) 0.0333(4) Uani 1 1 d . . .
H2A H 0.6496 0.7916 0.7722 0.040 Uiso 1 1 calc R . .
H2B H 0.6376 0.6710 0.8554 0.040 Uiso 1 1 calc R . .
C3 C 0.47678(17) 0.64757(18) 0.7444(3) 0.0350(4) Uani 1 1 d . . .
H3A H 0.4461 0.6314 0.8828 0.042 Uiso 1 1 calc R . .
H3B H 0.4537 0.7019 0.6818 0.042 Uiso 1 1 calc R . .
C4 C 0.42516(15) 0.53361(16) 0.6282(3) 0.0273(4) Uani 1 1 d . . .
C5 C 0.39593(15) 0.53106(16) 0.4370(3) 0.0296(4) Uani 1 1 d . . .
H5 H 0.3797 0.5901 0.3893 0.035 Uiso 1 1 calc R . .
C6 C 0.38764(16) 0.43868(16) 0.2942(3) 0.0292(4) Uani 1 1 d . . .
H6A H 0.3515 0.4438 0.1674 0.035 Uiso 1 1 calc R . .
H6B H 0.3369 0.3588 0.3515 0.035 Uiso 1 1 calc R . .
C7 C 0.51252(15) 0.45845(15) 0.2542(2) 0.0253(3) Uani 1 1 d . . .
H7A H 0.5599 0.5361 0.1876 0.030 Uiso 1 1 calc R . .
H7B H 0.5056 0.3968 0.1600 0.030 Uiso 1 1 calc R . .
C8 C 0.58091(13) 0.45575(14) 0.4408(2) 0.0202(3) Uani 1 1 d . . .
C9 C 0.67670(14) 0.57796(13) 0.5181(2) 0.0211(3) Uani 1 1 d . . .
H9 H 0.7077 0.5645 0.6461 0.025 Uiso 1 1 calc R . .
C10 C 0.78520(15) 0.65731(15) 0.3849(3) 0.0288(4) Uani 1 1 d . . .
H10A H 0.7665 0.6521 0.2408 0.035 Uiso 1 1 calc R . .
H10B H 0.8544 0.6469 0.4089 0.035 Uiso 1 1 calc R . .
C11 C 0.79395(15) 0.76780(15) 0.4894(3) 0.0309(4) Uani 1 1 d . . .
C12 C 0.43447(16) 0.43475(16) 0.7264(3) 0.0308(4) Uani 1 1 d . . .
H12A H 0.3533 0.3708 0.7590 0.037 Uiso 1 1 calc R . .
H12B H 0.4772 0.4649 0.8543 0.037 Uiso 1 1 calc R . .
C13 C 0.49658(14) 0.37939(14) 0.6077(2) 0.0247(3) Uani 1 1 d . . .
H13A H 0.5420 0.3594 0.7030 0.030 Uiso 1 1 calc R . .
H13B H 0.4347 0.3042 0.5480 0.030 Uiso 1 1 calc R . .
O14 O 0.64392(10) 0.39638(10) 0.37319(17) 0.0246(3) Uani 1 1 d . . .
H14 H 0.678(3) 0.388(3) 0.475(4) 0.047(7) Uiso 1 1 d . . .
C15 C 0.8196(2) 0.87252(19) 0.3562(4) 0.0474(5) Uani 1 1 d . . .
H15A H 0.7647 0.8451 0.2430 0.071 Uiso 1 1 calc R . .
H15B H 0.9012 0.9091 0.3069 0.071 Uiso 1 1 calc R . .
H15C H 0.8095 0.9308 0.4331 0.071 Uiso 1 1 calc R . .
C16 C 0.87865(18) 0.80762(17) 0.6667(4) 0.0403(5) Uani 1 1 d . . .
H16A H 0.8705 0.8670 0.7438 0.061 Uiso 1 1 calc R . .
H16B H 0.9602 0.8421 0.6182 0.061 Uiso 1 1 calc R . .
H16C H 0.8596 0.7393 0.7519 0.061 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.522(3) . ?
C1 C9 1.559(2) . ?
C1 C11 1.561(2) . ?
C2 C3 1.554(3) . ?
C3 C4 1.505(2) . ?
C4 C5 1.332(3) . ?
C4 C12 1.505(2) . ?
C5 C6 1.499(2) . ?
C6 C7 1.539(2) . ?
C7 C8 1.546(2) . ?
C8 O14 1.4542(17) . ?
C8 C13 1.535(2) . ?
C8 C9 1.542(2) . ?
C9 C10 1.551(2) . ?
C10 C11 1.554(2) . ?
C11 C15 1.521(3) . ?
C11 C16 1.525(3) . ?
C12 C13 1.547(2) . ?

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
C2 C1 C9 120.27(14) . . ?
C2 C1 C11 121.29(15) . . ?
C9 C1 C11 88.22(12) . . ?
C1 C2 C3 112.04(15) . . ?
C4 C3 C2 108.80(14) . . ?
C5 C4 C3 120.19(17) . . ?
C5 C4 C12 122.94(16) . . ?
C3 C4 C12 115.56(15) . . ?
C4 C5 C6 122.58(16) . . ?
C5 C6 C7 109.35(14) . . ?
C6 C7 C8 115.41(13) . . ?
O14 C8 C13 107.08(12) . . ?
O14 C8 C7 104.24(11) . . ?
C13 C8 C7 111.70(13) . . ?
O14 C8 C9 105.87(12) . . ?
C13 C8 C9 111.88(12) . . ?
C7 C8 C9 115.25(13) . . ?
C8 C9 C10 119.56(13) . . ?
C8 C9 C1 125.79(13) . . ?
C10 C9 C1 87.56(12) . . ?
C9 C10 C11 88.79(12) . . ?
C15 C11 C16 110.74(16) . . ?
C15 C11 C10 116.68(18) . . ?
C16 C11 C10 111.81(15) . . ?
C15 C11 C1 114.95(15) . . ?
C16 C11 C1 113.57(17) . . ?
C10 C11 C1 87.38(12) . . ?
C4 C12 C13 117.37(14) . . ?
C8 C13 C12 116.38(13) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        80.34
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_GS421
_database_code_depnum_ccdc_archive 'CCDC 2346929'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2020-06-25
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'C15 H24 O'
_chemical_formula_sum            'C15 H24 O'
_chemical_formula_weight         220.36
_chemical_absolute_configuration rmad
_chemical_oxdiff_formula         'C45 H72 O3 '
_chemical_oxdiff_usercomment     'from G. Stakanovs'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           ' P 31'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z+1/3
3 -x+y,-x,z+2/3

_symmetry_Int_Tables_number      144
_cell_length_a                   13.3360(4)
_cell_length_b                   13.3360(4)
_cell_length_c                   6.2105(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     956.56(5)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    3517
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      77.0260
_cell_measurement_theta_min      3.8230
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.74a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.1475
_exptl_crystal_F_000             366.9805
_exptl_crystal_description       Needle
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5016
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         77.2
_diffrn_reflns_theta_min         3.83
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.97
_diffrn_measured_fraction_theta_max 0.82
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     89.00 120.00   0.50    1.66    --   48.50  77.00 -90.00   62
  2  ω     89.00 119.00   0.50    1.66    --   48.50  77.00-180.00   60
  3  ω     99.00 128.00   0.50    6.66    --  107.75  45.00-120.00   58
  4  ω    136.00 173.00   0.50    6.66    --  107.75  59.00 -62.00   74
  5  ω    149.00 177.00   0.50    6.66    --  107.75  45.00-120.00   56
  6  ω     97.00 154.00   0.50    6.66    --  107.75  15.00 -60.00  114
  7  ω     41.00  66.00   0.50    6.66    --  107.75-125.00-120.00   50
  8  ω     38.00  64.00   0.50    6.66    --  107.75 -94.00-150.00   52
  9  ω     43.00  93.00   0.50    6.66    --  107.75 -94.00  90.00  100
 10  ω     90.00 134.00   0.50    6.66    --  107.75 -85.00 158.00   88
 11  ω     50.00  76.00   0.50    6.66    --  107.75 -85.00 158.00   52
 12  ω    102.00 128.00   0.50    6.66    --  107.75 125.00 -60.00   52
 13  ω    135.00 162.00   0.50    6.66    --  107.75 125.00-120.00   54
 14  ω    146.00 172.00   0.50    6.66    --  107.75 125.00 -60.00   52
 15  ω     35.00  63.00   0.50    6.66    --  107.75 -61.00 -30.00   56
 16  ω     35.00  60.00   0.50    6.66    --  107.75 -59.00 157.00   50
 17  ω     35.00  63.00   0.50    6.66    --  107.75 -61.00   0.00   56
 18  ω     40.00  67.00   0.50    6.66    --  107.75 -61.00 -60.00   54
 19  ω     35.00  66.00   0.50    6.66    --  107.75 -61.00-180.00   62
 20  ω   -120.00 -95.00   0.50    1.66    --  -48.50 -77.00-180.00   50
 21  ω   -119.00 -90.00   0.50    1.66    --  -48.50-125.00 -30.00   58
 22  ω    -98.00 -68.00   0.50    6.66    --  -86.25  82.00  80.00   60
 23  ω    -58.00 -19.00   0.50    6.66    --  -86.25  82.00  80.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0926854000
_diffrn_orient_matrix_UB_12      0.0179832000
_diffrn_orient_matrix_UB_13      0.1129682000
_diffrn_orient_matrix_UB_21      -0.0723136000
_diffrn_orient_matrix_UB_22      -0.0347996000
_diffrn_orient_matrix_UB_23      -0.2083964000
_diffrn_orient_matrix_UB_31      -0.0631394000
_diffrn_orient_matrix_UB_32      -0.1274906000
_diffrn_orient_matrix_UB_33      0.0728902000
_diffrn_oxdiff_digest_frames     
;
017a653d931ed41adda9fcb2840b1df93f0002772a8
;
_diffrn_oxdiff_digest_hkl        
;
017ac9ce67fca2e968f650f193c530dd71c8e9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.661
_reflns_limit_h_max              13
_reflns_limit_h_min              -14
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              7
_reflns_limit_l_min              -7
_reflns_number_gt                2167
_reflns_number_total             2221
_reflns_odcompleteness_completeness 98.02
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.74a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.1279
_refine_diff_density_min         -0.1189
_refine_diff_density_rms         0.0255
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_d_res_high            0.7905
_refine_ls_d_res_low             11.5493
_refine_ls_goodness_of_fit_ref   1.0618
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     151
_refine_ls_number_reflns         2221
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.0618
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+0.1392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0765
_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:
 C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12a,H12b), C7(H7a,H7b), C3(H3a,H3b), C6(H6a,H6b), C11(H11a,H11b),
 C13(H13a,H13b), C10(H10a,H10b)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O1 O 0.68067(4) 0.42115(4) 0.49871(4) 0.0224(2) Uani 1.000000 .
H1 H 0.70161(5) 0.40068(5) 0.40120(5) 0.04244(5) Uiso 1.000000 .
C8 C 0.87296(4) 0.78602(4) 0.65962(5) 0.0227(3) Uani 1.000000 .
C1 C 0.75064(4) 0.54591(4) 0.51735(5) 0.0184(2) Uani 1.000000 .
C4 C 0.52800(4) 0.61275(4) 0.36957(5) 0.0241(3) Uani 1.000000 .
C9 C 0.93475(4) 0.79234(4) 0.48726(5) 0.0250(3) Uani 1.000000 .
H9 H 0.95617(4) 0.85257(4) 0.38962(5) 0.0299(3) Uiso 1.000000 R
C2 C 0.68544(4) 0.60130(4) 0.40069(5) 0.0184(3) Uani 1.000000 .
H2 H 0.73301(4) 0.64717(4) 0.27894(5) 0.0221(3) Uiso 1.000000 R
C5 C 0.63726(4) 0.67272(4) 0.51733(5) 0.0203(3) Uani 1.000000 .
H5 H 0.61540(4) 0.64435(4) 0.66513(5) 0.0244(3) Uiso 1.000000 R
C12 C 0.76290(4) 0.56844(4) 0.75938(5) 0.0220(3) Uani 1.000000 .
H12a H 0.68709(4) 0.54603(4) 0.81780(5) 0.0264(3) Uiso 1.000000 R
H12b H 0.78829(4) 0.51878(4) 0.82441(5) 0.0264(3) Uiso 1.000000 R
C7 C 0.81137(5) 0.85482(4) 0.67523(5) 0.0300(3) Uani 1.000000 .
H7a H 0.78417(5) 0.85158(4) 0.82131(5) 0.0360(4) Uiso 1.000000 R
H7b H 0.86453(5) 0.93521(4) 0.63963(5) 0.0360(4) Uiso 1.000000 R
C3 C 0.56108(4) 0.51966(4) 0.31705(5) 0.0235(3) Uani 1.000000 .
H3a H 0.51869(4) 0.44931(4) 0.40094(5) 0.0281(3) Uiso 1.000000 R
H3b H 0.55767(4) 0.50217(4) 0.16471(5) 0.0281(3) Uiso 1.000000 R
C6 C 0.70848(4) 0.80469(4) 0.51929(5) 0.0279(3) Uani 1.000000 .
H6a H 0.73728(4) 0.83139(4) 0.37496(5) 0.0335(4) Uiso 1.000000 R
H6b H 0.65807(4) 0.83489(4) 0.55737(5) 0.0335(4) Uiso 1.000000 R
C11 C 0.86724(4) 0.58098(4) 0.40594(5) 0.0223(3) Uani 1.000000 .
H11a H 0.89052(4) 0.52559(4) 0.44842(5) 0.0268(3) Uiso 1.000000 R
H11b H 0.85361(4) 0.57265(4) 0.25186(5) 0.0268(3) Uiso 1.000000 R
C15 C 0.41287(4) 0.56866(5) 0.48494(5) 0.0342(3) Uani 1.000000 .
H15a H 0.41183(4) 0.52759(5) 0.61263(5) 0.0513(5) Uiso 1.000000 GR
H15b H 0.40319(4) 0.63301(5) 0.52364(5) 0.0513(5) Uiso 1.000000 GR
H15c H 0.35092(4) 0.51758(5) 0.39137(5) 0.0513(5) Uiso 1.000000 GR
C14 C 0.53395(5) 0.68267(5) 0.17155(5) 0.0379(4) Uani 1.000000 .
H14a H 0.52680(5) 0.74797(5) 0.21444(5) 0.0568(6) Uiso 1.000000 GR
H14b H 0.60681(5) 0.70933(5) 0.10015(5) 0.0568(6) Uiso 1.000000 GR
H14c H 0.47199(5) 0.63482(5) 0.07508(5) 0.0568(6) Uiso 1.000000 GR
C13 C 0.84780(5) 0.69493(5) 0.82755(5) 0.0327(3) Uani 1.000000 .
H13a H 0.92042(5) 0.70040(5) 0.86958(5) 0.0392(4) Uiso 1.000000 R
H13b H 0.81641(5) 0.71241(5) 0.95369(5) 0.0392(4) Uiso 1.000000 R
C10 C 0.97051(5) 0.70356(5) 0.44790(5) 0.0343(3) Uani 1.000000 .
H10a H 1.02212(5) 0.72730(5) 0.32476(5) 0.0411(4) Uiso 1.000000 R
H10b H 1.01324(5) 0.70084(5) 0.57203(5) 0.0411(4) Uiso 1.000000 R


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 H1 0.7717(7) . ?
O1 C1 1.4490(7) . ?
C8 C9 1.3276(6) . ?
C8 C7 1.5097(10) . ?
C8 C13 1.5061(7) . ?
C1 C2 1.5713(9) . ?
C1 C12 1.5256(4) . ?
C1 C11 1.5454(7) . ?
C4 C5 1.5618(6) . ?
C4 C3 1.5458(9) . ?
C4 C15 1.5212(7) . ?
C4 C14 1.5213(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.5013(10) . ?
C2 H2 0.9800 . ?
C2 C5 1.5674(9) . ?
C2 C3 1.5492(6) . ?
C5 H5 0.9800 . ?
C5 C6 1.5258(7) . ?
C12 H12a 0.9700 . ?
C12 H12b 0.9700 . ?
C12 C13 1.5481(7) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C7 C6 1.5331(6) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C6 H6a 0.9700 . ?
C6 H6b 0.9700 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 C10 1.5445(6) . ?
C15 H15a 0.9600 . ?
C15 H15b 0.9600 . ?
C15 H15c 0.9600 . ?
C14 H14a 0.9600 . ?
C14 H14b 0.9600 . ?
C14 H14c 0.9600 . ?
C13 H13a 0.9700 . ?
C13 H13b 0.9700 . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?

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 H1 109.25(5) . . ?
C7 C8 C9 121.48(4) . . ?
C13 C8 C9 119.37(6) . . ?
C13 C8 C7 118.44(4) . . ?
C2 C1 O1 108.24(4) . . ?
C12 C1 O1 104.42(3) . . ?
C12 C1 C2 113.06(5) . . ?
C11 C1 O1 106.53(5) . . ?
C11 C1 C2 111.15(3) . . ?
C11 C1 C12 112.89(4) . . ?
C3 C4 C5 88.14(4) . . ?
C15 C4 C5 115.09(3) . . ?
C15 C4 C3 115.29(4) . . ?
C14 C4 C5 114.31(4) . . ?
C14 C4 C3 111.92(4) . . ?
C14 C4 C15 110.54(5) . . ?
H9 C9 C8 119.57(4) . . ?
C10 C9 C8 120.86(4) . . ?
C10 C9 H9 119.568(19) . . ?
H2 C2 C1 108.15(2) . . ?
C5 C2 C1 124.33(3) . . ?
C5 C2 H2 108.15(2) . . ?
C3 C2 C1 118.28(4) . . ?
C3 C2 H2 108.146(17) . . ?
C3 C2 C5 87.82(4) . . ?
C2 C5 C4 88.75(4) . . ?
H5 C5 C4 109.352(19) . . ?
H5 C5 C2 109.35(2) . . ?
C6 C5 C4 118.60(5) . . ?
C6 C5 C2 119.78(4) . . ?
C6 C5 H5 109.352(16) . . ?
H12a C12 C1 108.38(3) . . ?
H12b C12 C1 108.38(4) . . ?
H12b C12 H12a 107.4 . . ?
C13 C12 C1 115.60(3) . . ?
C13 C12 H12a 108.38(3) . . ?
C13 C12 H12b 108.38(3) . . ?
H7a C7 C8 109.761(17) . . ?
H7b C7 C8 109.76(2) . . ?
H7b C7 H7a 108.2 . . ?
C6 C7 C8 109.55(4) . . ?
C6 C7 H7a 109.76(2) . . ?
C6 C7 H7b 109.76(3) . . ?
C2 C3 C4 89.99(4) . . ?
H3a C3 C4 113.64(2) . . ?
H3a C3 C2 113.64(2) . . ?
H3b C3 C4 113.643(17) . . ?
H3b C3 C2 113.643(19) . . ?
H3b C3 H3a 110.9 . . ?
C7 C6 C5 114.41(5) . . ?
H6a C6 C5 108.657(17) . . ?
H6a C6 C7 108.66(2) . . ?
H6b C6 C5 108.66(3) . . ?
H6b C6 C7 108.66(3) . . ?
H6b C6 H6a 107.6 . . ?
H11a C11 C1 107.73(3) . . ?
H11b C11 C1 107.727(19) . . ?
H11b C11 H11a 107.1 . . ?
C10 C11 C1 118.33(4) . . ?
C10 C11 H11a 107.73(3) . . ?
C10 C11 H11b 107.727(16) . . ?
H15a C15 C4 109.5 . . ?
H15b C15 C4 109.5 . . ?
H15b C15 H15a 109.5 . . ?
H15c C15 C4 109.5 . . ?
H15c C15 H15a 109.5 . . ?
H15c C15 H15b 109.5 . . ?
H14a C14 C4 109.5 . . ?
H14b C14 C4 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 C4 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C12 C13 C8 115.86(3) . . ?
H13a C13 C8 108.32(3) . . ?
H13a C13 C12 108.32(4) . . ?
H13b C13 C8 108.32(3) . . ?
H13b C13 C12 108.32(2) . . ?
H13b C13 H13a 107.4 . . ?
C11 C10 C9 113.29(5) . . ?
H10a C10 C9 108.916(19) . . ?
H10a C10 C11 108.92(2) . . ?
H10b C10 C9 108.916(19) . . ?
H10b C10 C11 108.92(3) . . ?
H10b C10 H10a 107.7 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.610
####################################################################### 
# 
# 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_GS714
_database_code_depnum_ccdc_archive 'CCDC 2346932'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-10
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         'C15 H24 O2'
_chemical_formula_sum            'C15 H24 O2'
_chemical_formula_weight         236.36
_chemical_absolute_configuration rmad
_chemical_oxdiff_formula         'C48 H78 O6'
_chemical_oxdiff_usercomment     'from Georgs'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           ' P 32'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z+2/3
3 -x+y,-x,z+1/3

_symmetry_Int_Tables_number      145
_cell_length_a                   13.03323(11)
_cell_length_b                   13.03323(11)
_cell_length_c                   6.70964(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     987.039(15)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    8573
_cell_measurement_temperature    150.0(1)
_cell_measurement_theta_max      79.3220
_cell_measurement_theta_min      3.9140
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.97714
_exptl_absorpt_correction_T_min  0.91205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.1928
_exptl_crystal_F_000             390
_exptl_crystal_description       'Needle '
_exptl_crystal_colour            'Colourless '
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9171
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         79.56
_diffrn_reflns_theta_min         3.92
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9806
_diffrn_measured_fraction_theta_max 0.9069
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    111.00 177.00   0.50    0.78    --  111.50  77.00   0.00  132
  2  ω    153.00 178.00   0.50    0.78    --  111.50  45.00 -60.00   50
  3  ω    108.00 134.00   0.50    0.78    --  111.50  45.00 -60.00   52
  4  ω    138.00 163.00   0.50    0.78    --  111.50  57.00-149.00   50
  5  ω     73.00  99.00   0.50    0.19    --   49.73  57.00-149.00   52
  6  ω    104.00 165.00   0.50    0.78    --  111.50  15.00   0.00  122
  7  ω    111.00 167.00   0.50    0.78    --  111.50  15.00 -60.00  112
  8  ω    105.00 157.00   0.50    0.78    --  111.50  15.00-150.00  104
  9  ω    115.00 141.00   0.50    0.78    --  111.50  30.00  90.00   52
 10  ω    145.00 177.00   0.50    0.78    --  111.50  30.00  90.00   64
 11  ω    104.00 153.00   0.50    0.78    --  111.50  30.00 150.00   98
 12  ω    -15.00  52.00   0.50    0.19    --   49.73 -57.00  69.00  134
 13  ω     41.00  89.00   0.50    0.78    --  111.50 -77.00 150.00   96
 14  ω     49.00  87.00   0.50    0.78    --  111.50 -77.00  90.00   76
 15  ω     47.00  72.00   0.50    0.78    --  111.50 -77.00   0.00   50
 16  ω     46.00  83.00   0.50    0.78    --  111.50 -77.00 -60.00   74
 17  ω     52.00  86.00   0.50    0.78    --  111.50 -77.00 -90.00   68
 18  ω     51.00  89.00   0.50    0.78    --  111.50 -77.00-120.00   76
 19  ω     41.00  91.00   0.50    0.78    --  111.50 -77.00-180.00  100
 20  ω     41.00  66.00   0.50    0.78    --  111.50 -61.00-180.00   50
 21  ω     41.00  66.00   0.50    0.78    --  111.50 -61.00-150.00   50
 22  ω     41.00  67.00   0.50    0.78    --  111.50 -61.00 -30.00   52
 23  ω     41.00  66.00   0.50    0.78    --  111.50 -61.00  30.00   50
 24  ω     41.00  66.00   0.50    0.78    --  111.50 -61.00  90.00   50
 25  ω     42.00  67.00   0.50    0.78    --  111.50 -61.00  60.00   50
 26  ω     45.00 104.00   0.50    0.78    --  111.50 -94.00 -30.00  118
 27  ω    -24.00  21.00   0.50    0.19    --  -49.73  57.00-149.00   90
 28  ω    -67.00 -42.00   0.50    0.78    --  -90.00  57.00-149.00   50
 29  ω    -44.00 -19.00   0.50    0.78    --  -90.00  30.00   0.00   50
 30  ω    -44.00 -19.00   0.50    0.78    --  -90.00  30.00  60.00   50
 31  ω   -118.00 -90.00   0.50    0.19    --  -49.73 -57.00  69.00   56
 32  ω   -121.00 -96.00   0.50    0.19    --  -49.73 -77.00 120.00   50
 33  ω   -143.00-118.00   0.50    0.78    --  -90.00 -57.00  69.00   50
 34  ω   -115.00 -84.00   0.50    0.19    --  -49.73-125.00  30.00   62
 35  ω   -122.00 -80.00   0.50    0.19    --  -49.73-125.00-150.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0529313000
_diffrn_orient_matrix_UB_12      -0.0718376000
_diffrn_orient_matrix_UB_13      -0.0913549000
_diffrn_orient_matrix_UB_21      0.1053918000
_diffrn_orient_matrix_UB_22      0.0594760000
_diffrn_orient_matrix_UB_23      0.1453600000
_diffrn_orient_matrix_UB_31      -0.0686605000
_diffrn_orient_matrix_UB_32      -0.0996269000
_diffrn_orient_matrix_UB_33      0.1524931000
_diffrn_oxdiff_digest_frames     
;
01908d12cfca8351d478075c558172709f0003020fd
;
_diffrn_oxdiff_digest_hkl        
;
013d137de26269a45dc21f5ecb95e2ae16d444
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.821
_reflns_limit_h_max              13
_reflns_limit_h_min              -13
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              8
_reflns_limit_l_min              -8
_reflns_number_gt                2593
_reflns_number_total             2601
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     78.17
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.1589
_refine_diff_density_min         -0.1736
_refine_diff_density_rms         0.0423
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_d_res_high            0.7839
_refine_ls_d_res_low             11.2871
_refine_ls_goodness_of_fit_ref   1.0837
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2601
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.0837
_refine_ls_shift/su_max          0.0025
_refine_ls_shift/su_mean         0.0003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0527P)²+0.0948P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0770
_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:
 C1(H1), C5(H5), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b), C10(H10a,H10b), C12(H12a,
 H12b), C13(H13a,H13b)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
C1 C 0.34076(9) 0.31439(9) 0.55102(17) 0.0196(2) Uani 1.000000 .
H1 H 0.39014(9) 0.31275(9) 0.43834(17) 0.0236(3) Uiso 1.000000 R
C2 C 0.38919(11) 0.29563(11) 0.74554(19) 0.0258(3) Uani 1.000000 .
H2a H 0.36432(11) 0.32830(11) 0.85663(19) 0.0310(3) Uiso 1.000000 R
H2b H 0.35433(11) 0.20953(11) 0.76882(19) 0.0310(3) Uiso 1.000000 R
C3 C 0.52541(11) 0.35453(11) 0.74666(19) 0.0259(3) Uani 1.000000 .
H3a H 0.55392(11) 0.36689(11) 0.88615(19) 0.0310(3) Uiso 1.000000 R
H3b H 0.54882(11) 0.30113(11) 0.68166(19) 0.0310(3) Uiso 1.000000 R
C4 C 0.58328(10) 0.47244(9) 0.63880(17) 0.0204(2) Uani 1.000000 .
C5 C 0.60953(9) 0.47201(10) 0.42722(17) 0.0204(2) Uani 1.000000 .
H5 H 0.58459(9) 0.39227(10) 0.36912(17) 0.0245(3) Uiso 1.000000 R
C6 C 0.60797(10) 0.56050(10) 0.28511(16) 0.0204(2) Uani 1.000000 .
H6a H 0.65749(10) 0.64143(10) 0.33923(16) 0.0245(3) Uiso 1.000000 R
H6b H 0.64221(10) 0.55620(10) 0.15580(16) 0.0245(3) Uiso 1.000000 R
C7 C 0.48092(9) 0.53622(10) 0.25242(16) 0.0180(2) Uani 1.000000 .
H7a H 0.48332(9) 0.59353(10) 0.15306(16) 0.0216(3) Uiso 1.000000 R
H7b H 0.43319(9) 0.45596(10) 0.19477(16) 0.0216(3) Uiso 1.000000 R
C8 C 0.41727(9) 0.54418(9) 0.44090(15) 0.0153(2) Uani 1.000000 .
C9 C 0.32326(9) 0.42368(9) 0.52432(15) 0.0163(2) Uani 1.000000 .
H9 H 0.29518(9) 0.43812(9) 0.65440(15) 0.0196(2) Uiso 1.000000 R
C10 C 0.21264(10) 0.34368(10) 0.39628(18) 0.0228(2) Uani 1.000000 .
H10a H 0.14346(10) 0.35324(10) 0.42573(18) 0.0273(3) Uiso 1.000000 R
H10b H 0.22869(10) 0.34923(10) 0.25130(18) 0.0273(3) Uiso 1.000000 R
C11 C 0.20695(10) 0.23330(10) 0.4969(2) 0.0243(2) Uani 1.000000 .
C12 C 0.56070(10) 0.56594(10) 0.73130(16) 0.0226(2) Uani 1.000000 .
H12a H 0.50867(10) 0.52967(10) 0.84841(16) 0.0271(3) Uiso 1.000000 R
H12b H 0.63738(10) 0.63039(10) 0.78188(16) 0.0271(3) Uiso 1.000000 R
C13 C 0.50507(9) 0.62313(9) 0.60208(15) 0.0179(2) Uani 1.000000 .
H13a H 0.56994(9) 0.69378(9) 0.53612(15) 0.0214(3) Uiso 1.000000 R
H13b H 0.46364(9) 0.65104(9) 0.69146(15) 0.0214(3) Uiso 1.000000 R
O14 O 0.35398(7) 0.60349(7) 0.37369(11) 0.01863(17) Uani 1.000000 .
H14 H 0.3203(18) 0.6119(16) 0.479(3) 0.037(4) Uiso 1.000000 .
C15 C 0.18035(12) 0.12923(12) 0.3607(2) 0.0371(3) Uani 1.000000 .
H15a H 0.2342(8) 0.1576(2) 0.2462(11) 0.0557(5) Uiso 1.000000 GR
H15b H 0.1915(12) 0.0707(6) 0.4346(6) 0.0557(5) Uiso 1.000000 GR
H15c H 0.0983(4) 0.0926(8) 0.3138(17) 0.0557(5) Uiso 1.000000 GR
C16 C 0.12520(12) 0.19190(11) 0.6772(2) 0.0332(3) Uani 1.000000 .
H16a H 0.1346(8) 0.1319(8) 0.7498(11) 0.0498(4) Uiso 1.000000 GR
H16b H 0.1454(7) 0.2595(2) 0.7650(10) 0.0498(4) Uiso 1.000000 GR
H16c H 0.04286(15) 0.1577(10) 0.6328(3) 0.0498(4) Uiso 1.000000 GR
O17 O 0.70437(7) 0.51410(8) 0.57199(14) 0.0266(2) Uani 1.000000 .


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
C1 C2 1.5219(16) . ?
C1 C9 1.5614(14) . ?
C1 C11 1.5644(15) . ?
C2 C3 1.5422(17) . ?
C3 C4 1.5150(15) . ?
C4 C5 1.4609(16) . ?
C4 C12 1.5216(16) . ?
C4 O17 1.4593(13) . ?
C5 C6 1.5044(15) . ?
C5 O17 1.4472(14) . ?
C6 C7 1.5382(15) . ?
C7 C8 1.5442(14) . ?
C8 C9 1.5351(14) . ?
C8 C13 1.5363(14) . ?
C8 O14 1.4555(11) . ?
C9 C10 1.5494(15) . ?
C10 C11 1.5568(16) . ?
C11 C15 1.5245(17) . ?
C11 C16 1.5215(18) . ?
C12 C13 1.5406(15) . ?

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
C9 C1 C2 120.43(10) . . ?
C11 C1 C2 120.17(10) . . ?
C11 C1 C9 88.15(8) . . ?
C3 C2 C1 113.01(10) . . ?
C4 C3 C2 111.59(9) . . ?
C5 C4 C3 117.33(10) . . ?
C12 C4 C3 114.83(10) . . ?
C12 C4 C5 122.61(9) . . ?
O17 C4 C3 114.92(9) . . ?
O17 C4 C5 59.42(7) . . ?
O17 C4 C12 115.69(9) . . ?
C6 C5 C4 121.33(9) . . ?
O17 C5 C4 60.24(7) . . ?
O17 C5 C6 118.11(9) . . ?
C7 C6 C5 111.00(9) . . ?
C8 C7 C6 115.38(9) . . ?
C9 C8 C7 114.24(8) . . ?
C13 C8 C7 112.10(8) . . ?
C13 C8 C9 112.01(8) . . ?
O14 C8 C7 104.37(8) . . ?
O14 C8 C9 106.37(8) . . ?
O14 C8 C13 107.01(8) . . ?
C8 C9 C1 124.69(8) . . ?
C10 C9 C1 87.76(8) . . ?
C10 C9 C8 118.98(9) . . ?
C11 C10 C9 88.85(8) . . ?
C10 C11 C1 87.39(8) . . ?
C15 C11 C1 114.90(9) . . ?
C15 C11 C10 116.55(12) . . ?
C16 C11 C1 113.66(11) . . ?
C16 C11 C10 111.95(10) . . ?
C16 C11 C15 110.70(11) . . ?
C13 C12 C4 118.96(9) . . ?
C12 C13 C8 116.44(8) . . ?
C5 O17 C4 60.35(7) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.348
_oxdiff_exptl_absorpt_empirical_full_min 0.527
####################################################################### 
# 
# 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_GS711
_database_code_depnum_ccdc_archive 'CCDC 2346930'
loop_
_audit_author_name
_audit_author_address
'Sergey Belyakov'
;Latvian Institute of Organic Synthesis
Latvia
;
_audit_update_record             
;
2024-04-09 deposited with the CCDC.	2024-07-11 downloaded from the CCDC.
;
_audit_creation_date             2022-02-14
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_chemical_formula_moiety         '4(C15 H24 O2)'
_chemical_formula_sum            'C60 H96 O8'
_chemical_formula_weight         945.43
_chemical_absolute_configuration rmad
_chemical_oxdiff_formula         'C120 H192 O16'
_chemical_oxdiff_usercomment     'from Georgs'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           ' P 2yb'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z

_symmetry_Int_Tables_number      4
_cell_length_a                   9.3483(1)
_cell_length_b                   17.5247(3)
_cell_length_c                   16.1772(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.546(1)
_cell_angle_gamma                90
_cell_volume                     2650.13(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    33174
_cell_measurement_temperature    170.0(1)
_cell_measurement_theta_max      79.3950
_cell_measurement_theta_min      3.7240
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
;
_exptl_crystal_density_diffrn    1.1847
_exptl_crystal_F_000             1040
_exptl_crystal_colour            Colourless
_exptl_crystal_description       'Needle '
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            47326
_diffrn_reflns_theta_full        75.0
_diffrn_reflns_theta_max         80.61
_diffrn_reflns_theta_min         2.73
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.0(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.9508
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -71.00   0.50    1.00    --  -49.73-129.00 166.00   94
  2  ω    -88.00 -43.00   0.50    1.00    --  -49.73 129.00-120.00   90
  3  ω   -117.00 -68.00   0.50    1.00    --  -49.73-140.00  -5.00   98
  4  ω    -71.00 -46.00   0.50    1.00    --  -49.73 140.00  52.00   50
  5  ω     38.00  87.00   0.50    1.00    --   49.73-129.00 166.00   98
  6  ω     66.00 103.00   0.50    1.00    --   49.73-140.00  -5.00   74
  7  ω   -140.00-115.00   0.50    4.00    --  -90.00-129.00 166.00   50
  8  ω    -83.00 -58.00   0.50    4.00    --  -90.00 140.00  52.00   50
  9  ω   -110.00 -85.00   0.50    4.00    --  -90.00-140.00  -5.00   50
 10  ω    -78.00 -53.00   0.50    4.00    --  -90.00 129.00-120.00   50
 11  ω    105.00 130.00   0.50    4.00    --  111.50 140.00  52.00   50
 12  ω     72.00 121.00   0.50    4.00    --  111.50-140.00  -5.00   98
 13  ω     65.00 114.00   0.50    4.00    --  111.50-129.00 166.00   98
 14  ω    114.00 139.00   0.50    4.00    --  111.50 129.00-120.00   50
 15  ω    -84.00 -54.00   0.50    1.00    --  -49.73 -19.00   0.00   60
 16  ω   -121.00 -92.00   0.50    1.00    --  -49.73 -77.00  30.00   58
 17  ω    -43.00  19.00   0.50    1.00    --  -49.73  19.00   0.00  124
 18  ω   -118.00 -93.00   0.50    1.00    --  -49.73 -19.00   0.00   50
 19  ω     93.00 118.00   0.50    1.00    --   49.73  77.00 -60.00   50
 20  ω     89.00 116.00   0.50    1.00    --   49.73  77.00-150.00   54
 21  ω     88.00 121.00   0.50    1.00    --   49.73  77.00 -30.00   66
 22  ω     89.00 120.00   0.50    1.00    --   49.73  77.00-120.00   62
 23  ω    -46.00 -20.00   0.50    4.00    --  -90.00  15.00-150.00   52
 24  ω   -152.00-100.00   0.50    4.00    --  -90.00 -30.00  30.00  104
 25  ω    -44.00 -18.00   0.50    4.00    --  -90.00  30.00 120.00   52
 26  ω     48.00  85.00   0.50    4.00    --  111.50 -77.00 -90.00   74
 27  ω    108.00 161.00   0.50    4.00    --  111.50  30.00-120.00  106
 28  ω    146.00 178.00   0.50    4.00    --  111.50 125.00-180.00   64
 29  ω     85.00 111.00   0.50    4.00    --  111.50-125.00  30.00   52
 30  ω     80.00 105.00   0.50    4.00    --  111.50 -94.00  60.00   50
 31  ω     41.00  68.00   0.50    4.00    --  111.50-125.00  60.00   54
 32  ω     43.00  70.00   0.50    4.00    --  111.50-125.00  30.00   54
 33  ω     80.00 105.00   0.50    4.00    --  111.50 -94.00   0.00   50
 34  ω     43.00 107.00   0.50    4.00    --  111.50-125.00 -60.00  128
 35  ω    130.00 157.00   0.50    4.00    --  111.50  15.00  90.00   54
 36  ω     66.00 101.00   0.50    4.00    --  111.50 -94.00-120.00   70
 37  ω     49.00  96.00   0.50    4.00    --  111.50-125.00-180.00   94
 38  ω     79.00 108.00   0.50    4.00    --  111.50-125.00  60.00   58
 39  ω    105.00 176.00   0.50    4.00    --  111.50  30.00 120.00  142
 40  ω    104.00 132.00   0.50    4.00    --  111.50 125.00 -60.00   56
 41  ω    104.00 131.00   0.50    4.00    --  111.50 -86.00-115.39   54
 42  ω     99.00 140.00   0.50    4.00    --  111.50 125.00-180.00   82
 43  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00   0.00   50
 44  ω    100.00 169.00   0.50    4.00    --  111.50 125.00 120.00  138
 45  ω     48.00 110.00   0.50    4.00    --  111.50-125.00  90.00  124
 46  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00 -60.00   50
 47  ω     55.00  82.00   0.50    4.00    --  111.50 -94.00-150.00   54
 48  ω    101.00 128.00   0.50    4.00    --  111.50 125.00 150.00   54
 49  ω     70.00 102.00   0.50    4.00    --  111.50 -94.00  90.00   64
 50  ω    104.00 172.00   0.50    4.00    --  111.50  45.00 -60.00  136
 51  ω    149.00 176.00   0.50    4.00    --  111.50 125.00 150.00   54
 52  ω     42.00  69.00   0.50    4.00    --  111.50 -85.00 122.44   54
 53  ω     90.00 133.00   0.50    4.00    --  111.50 -85.00 122.44   86
 54  ω    143.00 173.00   0.50    4.00    --  111.50  15.00 -90.00   60
 55  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00 -30.00   50
 56  ω     41.00  71.00   0.50    4.00    --  111.50 -94.00   0.00   60
 57  ω     41.00 105.00   0.50    4.00    --  111.50 -94.00-180.00  128
 58  ω     57.00  82.00   0.50    4.00    --  111.50 -77.00-180.00   50
 59  ω     42.00  67.00   0.50    4.00    --  111.50 -94.00  90.00   50
 60  ω     70.00 100.00   0.50    4.00    --  111.50 -94.00 -30.00   60
 61  ω     47.00  72.00   0.50    4.00    --  111.50-125.00   0.00   50
 62  ω    106.00 176.00   0.50    4.00    --  111.50  61.00-180.00  140
 63  ω     42.00  80.00   0.50    4.00    --  111.50-125.00 -90.00   76
 64  ω     84.00 109.00   0.50    4.00    --  111.50-125.00 -90.00   50
 65  ω    105.00 137.00   0.50    4.00    --  111.50  30.00  90.00   64
 66  ω    136.00 161.00   0.50    4.00    --  111.50 125.00-150.00   50
 67  ω    106.00 176.00   0.50    4.00    --  111.50  45.00 150.00  140
 68  ω    153.00 178.00   0.50    4.00    --  111.50 125.00 -60.00   50
 69  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00-150.00   50
 70  ω     41.00  66.00   0.50    4.00    --  111.50 -61.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku, XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0080978000
_diffrn_orient_matrix_UB_12      -0.0807914000
_diffrn_orient_matrix_UB_13      0.0373356000
_diffrn_orient_matrix_UB_21      -0.0353609000
_diffrn_orient_matrix_UB_22      -0.0345309000
_diffrn_orient_matrix_UB_23      -0.0853547000
_diffrn_orient_matrix_UB_31      0.1607280000
_diffrn_orient_matrix_UB_32      -0.0034952000
_diffrn_orient_matrix_UB_33      -0.0197393000
_diffrn_oxdiff_digest_frames     
;
01c07215f944e115f755dc99a2f4a45ed10003148c9
;
_diffrn_oxdiff_digest_hkl        
;
01190204f58cdaf43a5631c8a2eb4a746830e4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.912
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              -22
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                10764
_reflns_number_total             11054
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.49
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.2856
_refine_diff_density_min         -0.2631
_refine_diff_density_rms         0.0536
_refine_ls_abs_structure_details 
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_d_res_high            0.7814
_refine_ls_d_res_low             16.1765
_refine_ls_goodness_of_fit_ref   1.0337
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    140
_refine_ls_number_parameters     637
_refine_ls_number_reflns         11054
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0536
_refine_ls_restrained_S_all      1.0337
_refine_ls_shift/su_max          0.0014
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.9191P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1474
_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:
 C1(H1), C5(H5), C9(H9), C21(H21), C25(H25), C29(H29), C41(H41), C45(H45),
 C49(H49), C61(H61), C65(H65), C69(H69)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b), C6(H6a,H6b), C7(H7a,H7b), C10(H10a,H10b), C12(H12a,
 H12b), C13(H13a,H13b), C22(H22a,H22b), C23(H23a,H23b), C26(H26a,H26b),
 C27(H27a,H27b), C30(H30a,H30b), C32(H32a,H32b), C33(H33a,H33b), C42(H42a,H42b),
  C43(H43a,H43b), C46(H46a,H46b), C47(H47a,H47b), C50(H50a,H50b), C52(H52a,
 H52b), C53(H53a,H53b), C62(H62a,H62b), C63(H63a,H63b), C66(H66a,H66b),
 C67(H67a,H67b), C70(H70a,H70b), C72(H72a,H72b), C73(H73a,H73b)
2.c Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C16(H16a,H16b,H16c), C35(H35a,H35b,H35c), C36(H36a,H36b,
 H36c), C55(H55a,H55b,H55c), C56(H56a,H56b,H56c), C75(H75a,H75b,H75c), C76(H76a,
 H76b,H76c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
C1 C -0.0295(2) 0.64139(15) -0.03487(14) 0.0364(5) Uani 1.000000 .
H1 H 0.0187(2) 0.59071(15) -0.04048(14) 0.0437(6) Uiso 1.000000 R
C2 C -0.1178(3) 0.65785(18) -0.11191(16) 0.0464(6) Uani 1.000000 .
H2a H -0.1800(3) 0.70239(18) -0.10102(16) 0.0557(7) Uiso 1.000000 R
H2b H -0.0524(3) 0.67198(18) -0.15717(16) 0.0557(7) Uiso 1.000000 R
C3 C -0.2105(3) 0.59199(18) -0.14060(15) 0.0476(6) Uani 1.000000 .
H3a H -0.2810(3) 0.61117(18) -0.18167(15) 0.0571(7) Uiso 1.000000 R
H3b H -0.1495(3) 0.55399(18) -0.16865(15) 0.0571(7) Uiso 1.000000 R
C4 C -0.2899(3) 0.55279(15) -0.07149(14) 0.0383(5) Uani 1.000000 .
C5 C -0.4022(2) 0.59389(16) -0.02693(15) 0.0415(5) Uani 1.000000 .
H5 H -0.4151(2) 0.64913(16) -0.04061(15) 0.0498(6) Uiso 1.000000 R
C6 C -0.4370(2) 0.56969(17) 0.05988(16) 0.0428(5) Uani 1.000000 .
H6a H -0.5289(2) 0.59329(17) 0.07598(16) 0.0513(6) Uiso 1.000000 R
H6b H -0.4499(2) 0.51363(17) 0.06097(16) 0.0513(6) Uiso 1.000000 R
C7 C -0.3222(2) 0.59173(16) 0.12326(14) 0.0384(5) Uani 1.000000 .
H7a H -0.3338(2) 0.64661(16) 0.13609(14) 0.0460(6) Uiso 1.000000 R
H7b H -0.3408(2) 0.56304(16) 0.17477(14) 0.0460(6) Uiso 1.000000 R
C8 C -0.1652(2) 0.57815(13) 0.09924(12) 0.0300(4) Uani 1.000000 .
C9 C -0.1024(2) 0.64688(12) 0.05140(13) 0.0302(4) Uani 1.000000 .
H9 H -0.1767(2) 0.68783(12) 0.04863(13) 0.0362(5) Uiso 1.000000 R
C10 C 0.0389(3) 0.68278(15) 0.08442(17) 0.0448(6) Uani 1.000000 .
H10a H 0.0242(3) 0.72817(15) 0.11977(17) 0.0537(7) Uiso 1.000000 R
H10b H 0.1037(3) 0.64566(15) 0.11176(17) 0.0537(7) Uiso 1.000000 R
C11 C 0.0817(3) 0.70233(17) -0.00503(18) 0.0459(6) Uani 1.000000 .
C12 C -0.2164(3) 0.48582(15) -0.02801(16) 0.0426(5) Uani 1.000000 .
H12a H -0.2891(3) 0.44557(15) -0.01940(16) 0.0511(6) Uiso 1.000000 R
H12b H -0.1442(3) 0.46476(15) -0.06609(16) 0.0511(6) Uiso 1.000000 R
C13 C -0.1415(3) 0.50124(13) 0.05607(15) 0.0383(5) Uani 1.000000 .
H13a H -0.0373(3) 0.49521(13) 0.04786(15) 0.0460(6) Uiso 1.000000 R
H13b H -0.1714(3) 0.46060(13) 0.09473(15) 0.0460(6) Uiso 1.000000 R
O14 O -0.09516(18) 0.57303(11) 0.17934(10) 0.0398(4) Uani 1.000000 .
H14 H -0.004(4) 0.557(2) 0.170(2) 0.053(9) Uiso 1.000000 .
C15 C 0.2364(3) 0.6850(3) -0.0279(3) 0.0790(13) Uani 1.000000 .
H15a H 0.2628(14) 0.6344(10) -0.007(2) 0.1185(19) Uiso 1.000000 GR
H15b H 0.2460(10) 0.686(2) -0.0882(3) 0.1185(19) Uiso 1.000000 GR
H15c H 0.2997(5) 0.7235(13) -0.003(2) 0.1185(19) Uiso 1.000000 GR
C16 C 0.0434(4) 0.7843(2) -0.0278(3) 0.0680(10) Uani 1.000000 .
H16a H 0.050(3) 0.7908(5) -0.0879(3) 0.1019(15) Uiso 1.000000 GR
H16b H -0.0543(14) 0.7954(6) -0.0099(18) 0.1019(15) Uiso 1.000000 GR
H16c H 0.110(2) 0.8193(2) -0.0004(16) 0.1019(15) Uiso 1.000000 GR
O17 O -0.4410(2) 0.53926(14) -0.09074(13) 0.0567(5) Uani 1.000000 .
C21 C 0.4444(2) 0.32139(13) 0.23809(13) 0.0314(4) Uani 1.000000 .
H21 H 0.3684(2) 0.28127(13) 0.23537(13) 0.0376(5) Uiso 1.000000 R
C22 C 0.4508(3) 0.36175(15) 0.15561(14) 0.0385(5) Uani 1.000000 .
H22a H 0.5176(3) 0.40539(15) 0.16035(14) 0.0462(6) Uiso 1.000000 R
H22b H 0.4897(3) 0.32613(15) 0.11397(14) 0.0462(6) Uiso 1.000000 R
C23 C 0.3050(3) 0.39116(16) 0.12507(15) 0.0438(5) Uani 1.000000 .
H23a H 0.3195(3) 0.42224(16) 0.07473(15) 0.0525(7) Uiso 1.000000 R
H23b H 0.2446(3) 0.34693(16) 0.10948(15) 0.0525(7) Uiso 1.000000 R
C24 C 0.2261(2) 0.43864(14) 0.18793(14) 0.0354(5) Uani 1.000000 .
C25 C 0.2983(2) 0.50391(13) 0.22728(14) 0.0330(4) Uani 1.000000 .
H25 H 0.4012(2) 0.51130(13) 0.21295(14) 0.0396(5) Uiso 1.000000 R
C26 C 0.2550(3) 0.52999(14) 0.31223(16) 0.0441(6) Uani 1.000000 .
H26a H 0.3160(3) 0.57396(14) 0.32790(16) 0.0529(7) Uiso 1.000000 R
H26b H 0.1552(3) 0.54866(14) 0.30884(16) 0.0529(7) Uiso 1.000000 R
C27 C 0.2642(3) 0.47063(13) 0.38201(14) 0.0351(5) Uani 1.000000 .
H27a H 0.3471(3) 0.48439(13) 0.41752(14) 0.0421(5) Uiso 1.000000 R
H27b H 0.1776(3) 0.47645(13) 0.41614(14) 0.0421(5) Uiso 1.000000 R
C28 C 0.2785(2) 0.38536(12) 0.36036(12) 0.0287(4) Uani 1.000000 .
C29 C 0.4262(2) 0.36841(11) 0.31972(12) 0.0263(4) Uani 1.000000 .
H29 H 0.4798(2) 0.41750(11) 0.31424(12) 0.0315(4) Uiso 1.000000 R
C30 C 0.5252(2) 0.30905(13) 0.36212(14) 0.0334(4) Uani 1.000000 .
H30a H 0.5985(2) 0.33195(13) 0.39908(14) 0.0401(5) Uiso 1.000000 R
H30b H 0.4730(2) 0.26767(13) 0.39054(14) 0.0401(5) Uiso 1.000000 R
C31 C 0.5830(3) 0.28592(13) 0.27616(15) 0.0369(5) Uani 1.000000 .
C32 C 0.1043(3) 0.40272(17) 0.23513(16) 0.0443(6) Uani 1.000000 .
H32a H 0.0397(3) 0.44375(17) 0.25416(16) 0.0531(7) Uiso 1.000000 R
H32b H 0.0489(3) 0.36974(17) 0.19683(16) 0.0531(7) Uiso 1.000000 R
C33 C 0.1507(2) 0.35481(14) 0.31037(14) 0.0355(5) Uani 1.000000 .
H33a H 0.1745(2) 0.30281(14) 0.29092(14) 0.0426(5) Uiso 1.000000 R
H33b H 0.0681(2) 0.35024(14) 0.34788(14) 0.0426(5) Uiso 1.000000 R
O34 O 0.26911(18) 0.34390(10) 0.43711(10) 0.0356(3) Uani 1.000000 .
H34 H 0.319(5) 0.367(3) 0.473(3) 0.068(12) Uiso 1.000000 .
C35 C 0.6001(4) 0.20096(17) 0.26173(19) 0.0535(7) Uani 1.000000 .
H35a H 0.5129(11) 0.1744(2) 0.2787(15) 0.0802(10) Uiso 1.000000 GR
H35b H 0.617(3) 0.1915(2) 0.2029(3) 0.0802(10) Uiso 1.000000 GR
H35c H 0.6816(18) 0.1820(3) 0.2943(13) 0.0802(10) Uiso 1.000000 GR
C36 C 0.7200(3) 0.32860(17) 0.25371(19) 0.0477(6) Uani 1.000000 .
H36a H 0.7360(15) 0.3244(12) 0.1941(3) 0.0716(9) Uiso 1.000000 GR
H36b H 0.7104(11) 0.3825(3) 0.2688(14) 0.0716(9) Uiso 1.000000 GR
H36c H 0.8012(5) 0.3062(9) 0.2838(12) 0.0716(9) Uiso 1.000000 GR
O37 O 0.19550(18) 0.51654(11) 0.16067(11) 0.0426(4) Uani 1.000000 .
C41 C 0.4774(2) 0.36493(12) 0.78782(13) 0.0288(4) Uani 1.000000 .
H41 H 0.5148(2) 0.41794(12) 0.79550(13) 0.0346(5) Uiso 1.000000 R
C42 C 0.3876(2) 0.34315(16) 0.86161(14) 0.0397(5) Uani 1.000000 .
H42a H 0.3305(2) 0.29731(16) 0.84745(14) 0.0476(6) Uiso 1.000000 R
H42b H 0.4520(2) 0.32961(16) 0.90828(14) 0.0476(6) Uiso 1.000000 R
C43 C 0.2866(3) 0.40640(17) 0.88929(14) 0.0409(5) Uani 1.000000 .
H43a H 0.2163(3) 0.38473(17) 0.92820(14) 0.0491(6) Uiso 1.000000 R
H43b H 0.3425(3) 0.44569(17) 0.91940(14) 0.0491(6) Uiso 1.000000 R
C44 C 0.2068(2) 0.44404(14) 0.81827(14) 0.0337(4) Uani 1.000000 .
C45 C 0.1001(2) 0.39979(15) 0.77174(14) 0.0367(5) Uani 1.000000 .
H45 H 0.0925(2) 0.34437(15) 0.78576(14) 0.0441(6) Uiso 1.000000 R
C46 C 0.0654(2) 0.42158(16) 0.68443(15) 0.0388(5) Uani 1.000000 .
H46a H -0.0233(2) 0.39502(16) 0.66691(15) 0.0466(6) Uiso 1.000000 R
H46b H 0.0467(2) 0.47715(16) 0.68209(15) 0.0466(6) Uiso 1.000000 R
C47 C 0.1841(2) 0.40219(14) 0.62392(13) 0.0336(4) Uani 1.000000 .
H47a H 0.1797(2) 0.34671(14) 0.61264(13) 0.0403(5) Uiso 1.000000 R
H47b H 0.1630(2) 0.42879(14) 0.57120(13) 0.0403(5) Uiso 1.000000 R
C48 C 0.3388(2) 0.42194(13) 0.64991(12) 0.0288(4) Uani 1.000000 .
C49 C 0.4134(2) 0.35659(11) 0.69872(12) 0.0274(4) Uani 1.000000 .
H49 H 0.3492(2) 0.31094(11) 0.69766(12) 0.0328(5) Uiso 1.000000 R
C50 C 0.5645(2) 0.33137(13) 0.67099(14) 0.0344(4) Uani 1.000000 .
H50a H 0.5637(2) 0.28685(13) 0.63332(14) 0.0413(5) Uiso 1.000000 R
H50b H 0.6227(2) 0.37342(13) 0.64815(14) 0.0413(5) Uiso 1.000000 R
C51 C 0.6026(2) 0.31109(13) 0.76143(15) 0.0337(4) Uani 1.000000 .
C52 C 0.2758(3) 0.51232(14) 0.77620(16) 0.0401(5) Uani 1.000000 .
H52a H 0.2006(3) 0.55136(14) 0.76749(16) 0.0482(6) Uiso 1.000000 R
H52b H 0.3468(3) 0.53423(14) 0.81533(16) 0.0482(6) Uiso 1.000000 R
C53 C 0.3516(2) 0.49993(12) 0.69276(14) 0.0342(4) Uani 1.000000 .
H53a H 0.4546(2) 0.51047(12) 0.70153(14) 0.0411(5) Uiso 1.000000 R
H53b H 0.3150(2) 0.53897(12) 0.65370(14) 0.0411(5) Uiso 1.000000 R
O54 O 0.40810(17) 0.42932(10) 0.57024(9) 0.0365(3) Uani 1.000000 .
H54 H 0.496(4) 0.449(2) 0.580(2) 0.047(8) Uiso 1.000000 .
C55 C 0.7502(3) 0.33612(16) 0.79152(19) 0.0453(6) Uani 1.000000 .
H55a H 0.7640(10) 0.3903(4) 0.7789(14) 0.0679(8) Uiso 1.000000 GR
H55b H 0.7579(10) 0.3283(13) 0.8514(3) 0.0679(8) Uiso 1.000000 GR
H55c H 0.8236(3) 0.3059(10) 0.7637(11) 0.0679(8) Uiso 1.000000 GR
C56 C 0.5793(3) 0.22735(14) 0.78032(19) 0.0445(6) Uani 1.000000 .
H56a H 0.584(3) 0.2193(3) 0.8402(2) 0.0668(8) Uiso 1.000000 GR
H56b H 0.4851(11) 0.2116(4) 0.7593(13) 0.0668(8) Uiso 1.000000 GR
H56c H 0.6537(15) 0.19695(18) 0.7536(12) 0.0668(8) Uiso 1.000000 GR
O57 O 0.05372(18) 0.45330(13) 0.83442(12) 0.0507(5) Uani 1.000000 .
C61 C 0.9579(2) 0.68343(11) 0.51105(12) 0.0269(4) Uani 1.000000 .
H61 H 0.8858(2) 0.72543(11) 0.51464(12) 0.0323(5) Uiso 1.000000 R
C62 C 0.9625(2) 0.64196(14) 0.59325(13) 0.0340(4) Uani 1.000000 .
H62a H 1.0233(2) 0.59602(14) 0.58793(13) 0.0408(5) Uiso 1.000000 R
H62b H 1.0072(2) 0.67564(14) 0.63529(13) 0.0408(5) Uiso 1.000000 R
C63 C 0.8148(3) 0.61790(15) 0.62304(14) 0.0394(5) Uani 1.000000 .
H63a H 0.8261(3) 0.58690(15) 0.67384(14) 0.0473(6) Uiso 1.000000 R
H63b H 0.7595(3) 0.66413(15) 0.63751(14) 0.0473(6) Uiso 1.000000 R
C64 C 0.7310(2) 0.57242(13) 0.55972(13) 0.0315(4) Uani 1.000000 .
C65 C 0.7969(2) 0.50627(12) 0.51972(14) 0.0324(4) Uani 1.000000 .
H65 H 0.8992(2) 0.49634(12) 0.53470(14) 0.0388(5) Uiso 1.000000 R
C66 C 0.7514(3) 0.48220(14) 0.43408(16) 0.0447(6) Uani 1.000000 .
H66a H 0.8122(3) 0.43866(14) 0.41748(16) 0.0537(7) Uiso 1.000000 R
H66b H 0.6518(3) 0.46318(14) 0.43701(16) 0.0537(7) Uiso 1.000000 R
C67 C 0.7575(3) 0.54222(13) 0.36556(14) 0.0347(4) Uani 1.000000 .
H67a H 0.8347(3) 0.52698(13) 0.32746(14) 0.0416(5) Uiso 1.000000 R
H67b H 0.6665(3) 0.53907(13) 0.33394(14) 0.0416(5) Uiso 1.000000 R
C68 C 0.7817(2) 0.62653(12) 0.38772(12) 0.0279(4) Uani 1.000000 .
C69 C 0.9325(2) 0.63945(11) 0.42783(12) 0.0252(4) Uani 1.000000 .
H69 H 0.9833(2) 0.58929(11) 0.43105(12) 0.0302(4) Uiso 1.000000 R
C70 C 1.0339(2) 0.69888(12) 0.38767(13) 0.0293(4) Uani 1.000000 .
H70a H 1.1035(2) 0.67623(12) 0.34896(13) 0.0351(5) Uiso 1.000000 R
H70b H 0.9833(2) 0.74255(12) 0.36191(13) 0.0351(5) Uiso 1.000000 R
C71 C 1.0980(2) 0.71683(11) 0.47424(13) 0.0287(4) Uani 1.000000 .
C72 C 0.6103(2) 0.61093(15) 0.51204(15) 0.0381(5) Uani 1.000000 .
H72a H 0.5441(2) 0.57111(15) 0.49119(15) 0.0457(6) Uiso 1.000000 R
H72b H 0.5562(2) 0.64369(15) 0.55059(15) 0.0457(6) Uiso 1.000000 R
C73 C 0.6589(2) 0.65988(12) 0.43871(14) 0.0323(4) Uani 1.000000 .
H73a H 0.6891(2) 0.71039(12) 0.46003(14) 0.0387(5) Uiso 1.000000 R
H73b H 0.5757(2) 0.66817(12) 0.40145(14) 0.0387(5) Uiso 1.000000 R
O74 O 0.77349(18) 0.66816(9) 0.31080(10) 0.0361(3) Uani 1.000000 .
H74 H 0.831(4) 0.641(2) 0.274(2) 0.062(10) Uiso 1.000000 .
C75 C 1.1255(2) 0.80001(13) 0.49411(15) 0.0355(4) Uani 1.000000 .
H75a H 1.2048(15) 0.8188(4) 0.4605(10) 0.0533(7) Uiso 1.000000 GR
H75b H 1.0393(8) 0.8299(2) 0.4819(12) 0.0533(7) Uiso 1.000000 GR
H75c H 1.150(2) 0.80519(19) 0.5528(3) 0.0533(7) Uiso 1.000000 GR
C76 C 1.2313(2) 0.66971(14) 0.49330(15) 0.0362(5) Uani 1.000000 .
H76a H 1.2119(7) 0.6158(2) 0.4816(12) 0.0542(7) Uiso 1.000000 GR
H76b H 1.3104(6) 0.6874(8) 0.4588(9) 0.0542(7) Uiso 1.000000 GR
H76c H 1.2574(13) 0.6757(10) 0.5518(3) 0.0542(7) Uiso 1.000000 GR
O77 O 0.69420(18) 0.49510(10) 0.58564(11) 0.0405(4) Uani 1.000000 .


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
C1 C2 1.516(3) . ?
C1 C9 1.562(3) . ?
C1 C11 1.564(4) . ?
C2 C3 1.514(4) . ?
C3 C4 1.513(4) . ?
C4 C5 1.468(3) . ?
C4 C12 1.528(4) . ?
C4 O17 1.463(3) . ?
C5 C6 1.506(4) . ?
C5 O17 1.451(3) . ?
C6 C7 1.527(3) . ?
C7 C8 1.540(3) . ?
C8 C9 1.550(3) . ?
C8 C13 1.535(3) . ?
C8 O14 1.449(2) . ?
C9 C10 1.553(3) . ?
C10 C11 1.543(4) . ?
C11 C15 1.526(4) . ?
C11 C16 1.524(4) . ?
C12 C13 1.548(4) . ?
C21 C22 1.512(3) . ?
C21 C29 1.567(3) . ?
C21 C31 1.559(3) . ?
C22 C23 1.535(4) . ?
C23 C24 1.512(4) . ?
C24 C25 1.470(3) . ?
C24 C32 1.514(3) . ?
C24 O37 1.462(3) . ?
C25 C26 1.507(3) . ?
C25 O37 1.454(3) . ?
C26 C27 1.537(3) . ?
C27 C28 1.541(3) . ?
C28 C29 1.564(3) . ?
C28 C33 1.532(3) . ?
C28 O34 1.442(2) . ?
C29 C30 1.548(3) . ?
C30 C31 1.550(3) . ?
C31 C35 1.516(4) . ?
C31 C36 1.530(4) . ?
C32 C33 1.538(3) . ?
C41 C42 1.515(3) . ?
C41 C49 1.562(3) . ?
C41 C51 1.566(3) . ?
C42 C43 1.526(4) . ?
C43 C44 1.515(3) . ?
C44 C45 1.466(3) . ?
C44 C52 1.523(3) . ?
C44 O57 1.466(3) . ?
C45 C46 1.496(3) . ?
C45 O57 1.451(3) . ?
C46 C47 1.525(3) . ?
C47 C48 1.542(3) . ?
C48 C49 1.553(3) . ?
C48 C53 1.537(3) . ?
C48 O54 1.454(2) . ?
C49 C50 1.550(3) . ?
C50 C51 1.544(3) . ?
C51 C55 1.523(3) . ?
C51 C56 1.515(3) . ?
C52 C53 1.546(3) . ?
C61 C62 1.516(3) . ?
C61 C69 1.567(3) . ?
C61 C71 1.558(3) . ?
C62 C63 1.526(3) . ?
C63 C64 1.511(3) . ?
C64 C65 1.466(3) . ?
C64 C72 1.519(3) . ?
C64 O77 1.461(3) . ?
C65 C66 1.506(3) . ?
C65 O77 1.455(3) . ?
C66 C67 1.530(3) . ?
C67 C68 1.537(3) . ?
C68 C69 1.563(3) . ?
C68 C73 1.536(3) . ?
C68 O74 1.444(2) . ?
C69 C70 1.555(3) . ?
C70 C71 1.550(3) . ?
C71 C75 1.514(3) . ?
C71 C76 1.524(3) . ?
C72 C73 1.536(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C2 118.93(19) . . ?
C11 C1 C2 118.6(2) . . ?
C11 C1 C9 88.65(19) . . ?
C3 C2 C1 114.4(2) . . ?
C4 C3 C2 113.8(2) . . ?
C5 C4 C3 119.9(2) . . ?
C12 C4 C3 117.9(2) . . ?
C12 C4 C5 118.1(2) . . ?
O17 C4 C3 113.3(2) . . ?
O17 C4 C5 59.37(16) . . ?
O17 C4 C12 113.7(2) . . ?
C6 C5 C4 118.8(2) . . ?
O17 C5 C4 60.15(16) . . ?
O17 C5 C6 115.0(2) . . ?
C7 C6 C5 113.5(2) . . ?
C8 C7 C6 117.19(19) . . ?
C9 C8 C7 111.87(18) . . ?
C13 C8 C7 113.11(19) . . ?
C13 C8 C9 113.45(17) . . ?
O14 C8 C7 101.98(16) . . ?
O14 C8 C9 108.93(17) . . ?
O14 C8 C13 106.65(18) . . ?
C8 C9 C1 124.67(19) . . ?
C10 C9 C1 87.44(18) . . ?
C10 C9 C8 117.91(18) . . ?
C11 C10 C9 89.70(18) . . ?
C10 C11 C1 87.72(18) . . ?
C15 C11 C1 114.7(3) . . ?
C15 C11 C10 116.0(2) . . ?
C16 C11 C1 114.5(2) . . ?
C16 C11 C10 111.9(3) . . ?
C16 C11 C15 110.4(3) . . ?
C13 C12 C4 117.9(2) . . ?
C12 C13 C8 119.14(19) . . ?
C5 O17 C4 60.48(15) . . ?
C29 C21 C22 120.21(18) . . ?
C31 C21 C22 119.70(19) . . ?
C31 C21 C29 88.46(16) . . ?
C23 C22 C21 113.5(2) . . ?
C24 C23 C22 113.94(18) . . ?
C25 C24 C23 119.7(2) . . ?
C32 C24 C23 119.0(2) . . ?
C32 C24 C25 116.7(2) . . ?
O37 C24 C23 113.98(19) . . ?
O37 C24 C25 59.45(14) . . ?
O37 C24 C32 113.2(2) . . ?
C26 C25 C24 120.3(2) . . ?
O37 C25 C24 60.01(14) . . ?
O37 C25 C26 116.6(2) . . ?
C27 C26 C25 116.8(2) . . ?
C28 C27 C26 119.60(19) . . ?
C29 C28 C27 110.99(17) . . ?
C33 C28 C27 112.97(18) . . ?
C33 C28 C29 113.50(17) . . ?
O34 C28 C27 106.68(17) . . ?
O34 C28 C29 109.11(16) . . ?
O34 C28 C33 103.01(17) . . ?
C28 C29 C21 123.88(17) . . ?
C30 C29 C21 87.19(15) . . ?
C30 C29 C28 117.90(17) . . ?
C31 C30 C29 89.43(16) . . ?
C30 C31 C21 87.41(16) . . ?
C35 C31 C21 114.8(2) . . ?
C35 C31 C30 115.7(2) . . ?
C36 C31 C21 113.9(2) . . ?
C36 C31 C30 112.6(2) . . ?
C36 C31 C35 110.7(2) . . ?
C33 C32 C24 114.71(19) . . ?
C32 C33 C28 116.08(19) . . ?
C25 O37 C24 60.55(14) . . ?
C49 C41 C42 119.54(17) . . ?
C51 C41 C42 118.98(19) . . ?
C51 C41 C49 88.45(16) . . ?
C43 C42 C41 113.4(2) . . ?
C44 C43 C42 113.28(19) . . ?
C45 C44 C43 119.1(2) . . ?
C52 C44 C43 118.2(2) . . ?
C52 C44 C45 118.4(2) . . ?
O57 C44 C43 112.79(18) . . ?
O57 C44 C45 59.31(15) . . ?
O57 C44 C52 114.3(2) . . ?
C46 C45 C44 119.4(2) . . ?
O57 C45 C44 60.36(14) . . ?
O57 C45 C46 115.6(2) . . ?
C47 C46 C45 113.38(19) . . ?
C48 C47 C46 117.47(18) . . ?
C49 C48 C47 112.88(17) . . ?
C53 C48 C47 113.03(18) . . ?
C53 C48 C49 113.21(16) . . ?
O54 C48 C47 101.72(15) . . ?
O54 C48 C49 108.35(16) . . ?
O54 C48 C53 106.70(17) . . ?
C48 C49 C41 124.50(17) . . ?
C50 C49 C41 87.22(15) . . ?
C50 C49 C48 117.97(17) . . ?
C51 C50 C49 89.67(16) . . ?
C50 C51 C41 87.31(16) . . ?
C55 C51 C41 114.62(19) . . ?
C55 C51 C50 115.9(2) . . ?
C56 C51 C41 114.79(19) . . ?
C56 C51 C50 112.4(2) . . ?
C56 C51 C55 110.3(2) . . ?
C53 C52 C44 118.65(19) . . ?
C52 C53 C48 118.99(18) . . ?
C45 O57 C44 60.33(14) . . ?
C69 C61 C62 121.37(17) . . ?
C71 C61 C62 119.91(17) . . ?
C71 C61 C69 88.70(15) . . ?
C63 C62 C61 113.05(18) . . ?
C64 C63 C62 113.34(18) . . ?
C65 C64 C63 120.0(2) . . ?
C72 C64 C63 119.2(2) . . ?
C72 C64 C65 116.12(19) . . ?
O77 C64 C63 114.63(18) . . ?
O77 C64 C65 59.61(14) . . ?
O77 C64 C72 112.45(18) . . ?
C66 C65 C64 120.8(2) . . ?
O77 C65 C64 60.00(14) . . ?
O77 C65 C66 117.02(19) . . ?
C67 C66 C65 117.51(19) . . ?
C68 C67 C66 119.90(19) . . ?
C69 C68 C67 111.51(17) . . ?
C73 C68 C67 112.46(18) . . ?
C73 C68 C69 113.45(16) . . ?
O74 C68 C67 106.15(16) . . ?
O74 C68 C69 108.98(16) . . ?
O74 C68 C73 103.68(16) . . ?
C68 C69 C61 123.81(16) . . ?
C70 C69 C61 86.66(14) . . ?
C70 C69 C68 118.35(16) . . ?
C71 C70 C69 89.45(15) . . ?
C70 C71 C61 87.14(14) . . ?
C75 C71 C61 114.98(17) . . ?
C75 C71 C70 116.79(18) . . ?
C76 C71 C61 114.07(17) . . ?
C76 C71 C70 112.39(18) . . ?
C76 C71 C75 109.97(17) . . ?
C73 C72 C64 114.60(17) . . ?
C72 C73 C68 115.50(18) . . ?
C65 O77 C64 60.38(13) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.448
_oxdiff_exptl_absorpt_empirical_full_min 0.631
