# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_cu_2021812_0m
_database_code_depnum_ccdc_archive 'CCDC 2174239'
loop_
_audit_author_name
_audit_author_address
wumengjun
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H30 O'
_chemical_formula_sum            'C20 H30 O'
_chemical_formula_weight         286.44
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   9.02720(10)
_cell_length_b                   9.02720(10)
_cell_length_c                   36.5504(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2579.46(10)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9394
_cell_measurement_temperature    110
_cell_measurement_theta_max      74.854
_cell_measurement_theta_min      3.613
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1436 before and 0.0805 after correction. The Ratio of minimum to maximum transmission is 0.8813. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.106
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             948
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            44959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.581
_diffrn_reflns_theta_min         3.628
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3413
_reflns_number_total             3521
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.131
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.5018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0783
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C11(H11), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C12(H12A,H12B), C9(H9A,H9B), C3(H3A,H3B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61882(16) 1.21408(17) 0.68550(3) 0.0356(3) Uani 1 1 d . . . . .
C6 C 0.53241(18) 0.96291(18) 0.59953(4) 0.0203(3) Uani 1 1 d . . . . .
H6 H 0.475490 0.835715 0.597151 0.024 Uiso 1 1 calc R . . . .
C5 C 0.41616(19) 1.02577(18) 0.58209(4) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.489696 1.149812 0.576042 0.026 Uiso 1 1 calc R . . . .
C4 C 0.29676(19) 0.9400(2) 0.55022(4) 0.0252(3) Uani 1 1 d . . . . .
C13 C 0.6239(2) 1.1777(2) 0.65368(4) 0.0256(3) Uani 1 1 d . . . . .
C14 C 0.49187(19) 1.0090(2) 0.63804(4) 0.0227(3) Uani 1 1 d . . . . .
H14 H 0.455969 0.913300 0.655948 0.027 Uiso 1 1 calc R . . . .
C10 C 0.5670(2) 0.7182(2) 0.53744(4) 0.0284(3) Uani 1 1 d . . . . .
C15 C 0.33427(19) 1.0126(2) 0.62057(4) 0.0250(3) Uani 1 1 d . . . . .
C11 C 0.84772(19) 1.19639(19) 0.61116(4) 0.0246(3) Uani 1 1 d . . . . .
H11 H 0.885165 1.148979 0.631591 0.030 Uiso 1 1 calc R . . . .
C8 C 0.7826(2) 0.9124(2) 0.58478(4) 0.0266(3) Uani 1 1 d . . . . .
H8A H 0.906380 0.971225 0.590427 0.032 Uiso 1 1 calc R . . . .
H8B H 0.722636 0.823898 0.603771 0.032 Uiso 1 1 calc R . . . .
C7 C 0.72099(19) 1.04397(19) 0.58715(4) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.727842 1.089469 0.561887 0.026 Uiso 1 1 calc R . . . .
C12 C 0.7666(2) 1.2944(2) 0.62839(5) 0.0287(3) Uani 1 1 d . . . . .
H12A H 0.854298 1.394082 0.642239 0.034 Uiso 1 1 calc R . . . .
H12B H 0.721220 1.337050 0.608919 0.034 Uiso 1 1 calc R . . . .
C19 C 0.1720(2) 0.8425(2) 0.62801(5) 0.0332(4) Uani 1 1 d . . . . .
H19A H 0.080627 0.830714 0.611676 0.050 Uiso 1 1 calc GR . . . .
H19B H 0.136841 0.839203 0.653497 0.050 Uiso 1 1 calc GR . . . .
H19C H 0.194380 0.748358 0.623616 0.050 Uiso 1 1 calc GR . . . .
C1 C 0.4921(2) 0.7851(2) 0.51747(4) 0.0318(4) Uani 1 1 d . . . . .
H1 H 0.565417 0.891655 0.505977 0.038 Uiso 1 1 calc R . . . .
C9 C 0.7532(2) 0.8234(2) 0.54743(5) 0.0308(4) Uani 1 1 d . . . . .
H9A H 0.813108 0.911287 0.528334 0.037 Uiso 1 1 calc R . . . .
H9B H 0.803907 0.748326 0.547865 0.037 Uiso 1 1 calc R . . . .
C3 C 0.2203(2) 0.7499(2) 0.54360(5) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.096240 0.698633 0.538807 0.038 Uiso 1 1 calc R . . . .
H3B H 0.233822 0.696043 0.565991 0.038 Uiso 1 1 calc R . . . .
C18 C 1.0069(2) 1.3185(2) 0.58941(5) 0.0334(4) Uani 1 1 d . . . . .
H18A H 1.053505 1.253581 0.577361 0.050 Uiso 1 1 calc GR . . . .
H18B H 1.092908 1.402954 0.606002 0.050 Uiso 1 1 calc GR . . . .
H18C H 0.976492 1.377227 0.570893 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.2547(2) 1.0315(2) 0.52866(5) 0.0335(4) Uani 1 1 d . . . . .
H16A H 0.299629 1.149925 0.533317 0.040 Uiso 1 1 calc R . . . .
H16B H 0.179751 0.978637 0.508559 0.040 Uiso 1 1 calc R . . . .
C20 C 0.3055(2) 1.1602(2) 0.63024(5) 0.0341(4) Uani 1 1 d . . . . .
H20A H 0.409944 1.268876 0.625188 0.051 Uiso 1 1 calc GR . . . .
H20B H 0.276828 1.154207 0.656255 0.051 Uiso 1 1 calc GR . . . .
H20C H 0.211282 1.152579 0.615496 0.051 Uiso 1 1 calc GR . . . .
C17 C 0.4739(2) 0.5424(2) 0.55418(5) 0.0366(4) Uani 1 1 d . . . . .
H17A H 0.476321 0.552410 0.580898 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.529798 0.477909 0.546824 0.055 Uiso 1 1 calc GR . . . .
H17C H 0.354944 0.482555 0.545714 0.055 Uiso 1 1 calc GR . . . .
C2 C 0.3038(3) 0.7099(2) 0.51117(5) 0.0381(4) Uani 1 1 d . . . . .
H2A H 0.249699 0.584501 0.508147 0.046 Uiso 1 1 calc R . . . .
H2B H 0.285014 0.757715 0.488409 0.046 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
O1 C13 1.2157(19) . ?
C6 H6 1.0000 . ?
C6 C5 1.557(2) . ?
C6 C14 1.562(2) . ?
C6 C7 1.547(2) . ?
C5 H5 1.0000 . ?
C5 C4 1.511(2) . ?
C5 C15 1.566(2) . ?
C4 C3 1.515(2) . ?
C4 C16 1.327(2) . ?
C13 C14 1.500(2) . ?
C13 C12 1.505(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.574(2) . ?
C10 C1 1.327(3) . ?
C10 C9 1.505(2) . ?
C10 C17 1.505(2) . ?
C15 C19 1.526(2) . ?
C15 C20 1.521(2) . ?
C11 H11 1.0000 . ?
C11 C7 1.548(2) . ?
C11 C12 1.538(2) . ?
C11 C18 1.525(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.546(2) . ?
C8 C9 1.538(2) . ?
C7 H7 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.500(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.541(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 H6 109.3 . . ?
C5 C6 C14 88.94(11) . . ?
C14 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
C7 C6 C5 119.39(12) . . ?
C7 C6 C14 119.11(12) . . ?
C6 C5 H5 107.9 . . ?
C6 C5 C15 89.04(11) . . ?
C4 C5 C6 124.53(13) . . ?
C4 C5 H5 107.9 . . ?
C4 C5 C15 117.71(13) . . ?
C15 C5 H5 107.9 . . ?
C5 C4 C3 120.51(13) . . ?
C16 C4 C5 119.44(15) . . ?
C16 C4 C3 120.01(14) . . ?
O1 C13 C14 121.37(15) . . ?
O1 C13 C12 122.20(15) . . ?
C14 C13 C12 116.36(13) . . ?
C6 C14 H14 112.2 . . ?
C6 C14 C15 88.54(11) . . ?
C13 C14 C6 116.14(13) . . ?
C13 C14 H14 112.2 . . ?
C13 C14 C15 113.64(13) . . ?
C15 C14 H14 112.2 . . ?
C1 C10 C9 120.55(15) . . ?
C1 C10 C17 124.10(17) . . ?
C9 C10 C17 115.16(15) . . ?
C5 C15 C14 88.21(11) . . ?
C19 C15 C5 114.55(13) . . ?
C19 C15 C14 109.25(13) . . ?
C20 C15 C5 115.03(13) . . ?
C20 C15 C14 118.40(14) . . ?
C20 C15 C19 109.99(14) . . ?
C7 C11 H11 107.5 . . ?
C12 C11 H11 107.5 . . ?
C12 C11 C7 112.99(12) . . ?
C18 C11 H11 107.5 . . ?
C18 C11 C7 110.93(13) . . ?
C18 C11 C12 110.21(13) . . ?
H8A C8 H8B 107.6 . . ?
C7 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C9 C8 C7 114.62(13) . . ?
C6 C7 C11 113.84(12) . . ?
C6 C7 H7 107.0 . . ?
C11 C7 H7 107.0 . . ?
C8 C7 C6 112.74(12) . . ?
C8 C7 C11 108.96(12) . . ?
C8 C7 H7 107.0 . . ?
C13 C12 C11 109.62(13) . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C1 H1 116.6 . . ?
C10 C1 C2 126.72(16) . . ?
C2 C1 H1 116.6 . . ?
C10 C9 C8 113.06(13) . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C4 C3 C2 112.85(14) . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C16 H16A 120.0 . . ?
C4 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C2 C3 110.65(13) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?

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

data_cu_0729_0m
_database_code_depnum_ccdc_archive 'CCDC 2174244'
loop_
_audit_author_name
_audit_author_address
wumengjun
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2022-05-23 deposited with the CCDC.	2022-09-13 downloaded from the CCDC.
;
_audit_creation_date             2021-07-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H30 O'
_chemical_formula_sum            'C20 H30 O'
_chemical_formula_weight         286.44
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.3034(2)
_cell_length_b                   16.0980(5)
_cell_length_c                   16.7484(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1699.50(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    170
_cell_measurement_theta_max      74.354
_cell_measurement_theta_min      5.282
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.6906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1315 before and 0.0813 after correction. The Ratio of minimum to maximum transmission is 0.9162. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0651
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            39324
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.482
_diffrn_reflns_theta_min         3.808
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3255
_reflns_number_total             3463
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 1316 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3463
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0328
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0288P)²+0.3054P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0752
_refine_ls_wR_factor_ref         0.0773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C5(H5), C14(H14), C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C3(H3A,H3B), C12(H12A,H12B), C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1)
2.d X=CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C18(H18A,H18B,H18C), C17(H17A,H17B,
 H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2625(2) 0.56012(10) 0.50916(9) 0.0475(4) Uani 1 1 d . . . . .
C6 C 0.6510(3) 0.48474(10) 0.63665(9) 0.0238(3) Uani 1 1 d . . . . .
H6 H 0.532297 0.501561 0.672799 0.029 Uiso 1 1 calc R . . . .
C5 C 0.6665(3) 0.38836(10) 0.63485(10) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.806690 0.373498 0.610801 0.030 Uiso 1 1 calc R . . . .
C4 C 0.6304(3) 0.33149(10) 0.70490(10) 0.0288(4) Uani 1 1 d . . . . .
C14 C 0.5670(3) 0.47875(11) 0.54984(10) 0.0273(3) Uani 1 1 d . . . . .
H14 H 0.692974 0.476687 0.513613 0.033 Uiso 1 1 calc R . . . .
C13 C 0.4465(3) 0.55555(12) 0.53031(10) 0.0337(4) Uani 1 1 d . . . . .
C15 C 0.4958(3) 0.38825(10) 0.56510(9) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.9647(3) 0.55247(12) 0.71727(11) 0.0324(4) Uani 1 1 d . . . . .
H8A H 1.023569 0.496170 0.725943 0.039 Uiso 1 1 calc R . . . .
H8B H 1.086095 0.589859 0.706526 0.039 Uiso 1 1 calc R . . . .
C7 C 0.8274(3) 0.54949(10) 0.64139(10) 0.0273(3) Uani 1 1 d . . . . .
H7 H 0.926545 0.536965 0.596349 0.033 Uiso 1 1 calc R . . . .
C10 C 0.6962(3) 0.52116(12) 0.82864(10) 0.0325(4) Uani 1 1 d . . . . .
C9 C 0.8614(3) 0.58067(12) 0.79586(11) 0.0361(4) Uani 1 1 d . . . . .
H9A H 0.974036 0.588070 0.836438 0.043 Uiso 1 1 calc R . . . .
H9B H 0.793814 0.635438 0.787181 0.043 Uiso 1 1 calc R . . . .
C3 C 0.4702(3) 0.35244(12) 0.76958(10) 0.0346(4) Uani 1 1 d . . . . .
H3A H 0.372817 0.304819 0.777084 0.042 Uiso 1 1 calc R . . . .
H3B H 0.384591 0.400842 0.752478 0.042 Uiso 1 1 calc R . . . .
C11 C 0.7214(3) 0.63399(10) 0.62085(10) 0.0313(4) Uani 1 1 d . . . . .
H11 H 0.623383 0.648269 0.665745 0.038 Uiso 1 1 calc R . . . .
C12 C 0.5869(3) 0.63116(12) 0.54293(12) 0.0385(4) Uani 1 1 d . . . . .
H12A H 0.495443 0.681135 0.541824 0.046 Uiso 1 1 calc R . . . .
H12B H 0.685196 0.635208 0.496979 0.046 Uiso 1 1 calc R . . . .
C19 C 0.2660(3) 0.38020(12) 0.59262(11) 0.0344(4) Uani 1 1 d . . . . .
H19A H 0.244132 0.325300 0.616517 0.052 Uiso 1 1 calc GR . . . .
H19B H 0.171075 0.386866 0.546714 0.052 Uiso 1 1 calc GR . . . .
H19C H 0.235106 0.423283 0.632295 0.052 Uiso 1 1 calc GR . . . .
C1 C 0.7393(3) 0.44067(12) 0.83534(10) 0.0353(4) Uani 1 1 d . . . . .
H1 H 0.883789 0.424639 0.830681 0.042 Uiso 1 1 calc R . . . .
C20 C 0.5404(3) 0.32549(12) 0.49955(11) 0.0358(4) Uani 1 1 d . . . . .
H20A H 0.683298 0.334649 0.478249 0.054 Uiso 1 1 calc GR . . . .
H20B H 0.436077 0.332152 0.456635 0.054 Uiso 1 1 calc GR . . . .
H20C H 0.530585 0.269170 0.521444 0.054 Uiso 1 1 calc GR . . . .
C2 C 0.5802(4) 0.37258(12) 0.84963(11) 0.0390(4) Uani 1 1 d . . . . .
H2A H 0.473762 0.390810 0.889419 0.047 Uiso 1 1 calc R . . . .
H2B H 0.652466 0.322494 0.870513 0.047 Uiso 1 1 calc R . . . .
C18 C 0.8826(4) 0.70467(12) 0.61340(14) 0.0439(5) Uani 1 1 d . . . . .
H18A H 0.947096 0.715380 0.665637 0.066 Uiso 1 1 calc GR . . . .
H18B H 0.810671 0.754973 0.594605 0.066 Uiso 1 1 calc GR . . . .
H18C H 0.993255 0.688918 0.575186 0.066 Uiso 1 1 calc GR . . . .
C17 C 0.4840(3) 0.55798(14) 0.84857(13) 0.0451(5) Uani 1 1 d . . . . .
H17A H 0.503579 0.605901 0.883892 0.068 Uiso 1 1 calc GR . . . .
H17B H 0.396455 0.516197 0.875486 0.068 Uiso 1 1 calc GR . . . .
H17C H 0.413514 0.575882 0.799343 0.068 Uiso 1 1 calc GR . . . .
C16 C 0.7366(4) 0.26055(12) 0.70884(12) 0.0434(5) Uani 1 1 d . . . . .
H16A H 0.833926 0.246186 0.667795 0.052 Uiso 1 1 calc R . . . .
H16B H 0.715349 0.224066 0.752698 0.052 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
O1 C13 1.215(2) . ?
C6 H6 1.0000 . ?
C6 C5 1.555(2) . ?
C6 C14 1.550(2) . ?
C6 C7 1.526(2) . ?
C5 H5 1.0000 . ?
C5 C4 1.506(2) . ?
C5 C15 1.588(2) . ?
C4 C3 1.519(3) . ?
C4 C16 1.325(3) . ?
C14 H14 1.0000 . ?
C14 C13 1.487(3) . ?
C14 C15 1.546(2) . ?
C13 C12 1.520(3) . ?
C15 C19 1.526(2) . ?
C15 C20 1.518(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.538(2) . ?
C8 C9 1.537(3) . ?
C7 H7 1.0000 . ?
C7 C11 1.554(2) . ?
C10 C9 1.518(3) . ?
C10 C1 1.329(3) . ?
C10 C17 1.500(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.544(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.557(3) . ?
C11 C18 1.531(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C2 1.505(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C16 H16A 0.9500 . ?
C16 H16B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 H6 109.2 . . ?
C14 C6 H6 109.2 . . ?
C14 C6 C5 86.63(12) . . ?
C7 C6 H6 109.2 . . ?
C7 C6 C5 129.54(15) . . ?
C7 C6 C14 109.90(13) . . ?
C6 C5 H5 107.6 . . ?
C6 C5 C15 88.44(12) . . ?
C4 C5 C6 125.60(14) . . ?
C4 C5 H5 107.6 . . ?
C4 C5 C15 118.03(14) . . ?
C15 C5 H5 107.6 . . ?
C5 C4 C3 121.42(15) . . ?
C16 C4 C5 119.10(17) . . ?
C16 C4 C3 119.45(17) . . ?
C6 C14 H14 107.4 . . ?
C13 C14 C6 109.20(14) . . ?
C13 C14 H14 107.4 . . ?
C13 C14 C15 132.20(16) . . ?
C15 C14 C6 90.16(12) . . ?
C15 C14 H14 107.4 . . ?
O1 C13 C14 126.99(19) . . ?
O1 C13 C12 123.23(19) . . ?
C14 C13 C12 109.76(15) . . ?
C14 C15 C5 85.63(12) . . ?
C19 C15 C5 114.91(13) . . ?
C19 C15 C14 113.93(14) . . ?
C20 C15 C5 114.03(14) . . ?
C20 C15 C14 116.99(14) . . ?
C20 C15 C19 109.74(15) . . ?
H8A C8 H8B 107.1 . . ?
C7 C8 H8A 107.7 . . ?
C7 C8 H8B 107.7 . . ?
C9 C8 H8A 107.7 . . ?
C9 C8 H8B 107.7 . . ?
C9 C8 C7 118.58(15) . . ?
C6 C7 C8 118.30(14) . . ?
C6 C7 H7 106.2 . . ?
C6 C7 C11 105.83(14) . . ?
C8 C7 H7 106.2 . . ?
C8 C7 C11 113.42(14) . . ?
C11 C7 H7 106.2 . . ?
C1 C10 C9 120.37(18) . . ?
C1 C10 C17 123.29(19) . . ?
C17 C10 C9 116.28(17) . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 C8 114.46(15) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C4 C3 C2 111.55(16) . . ?
H3A C3 H3B 108.0 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C7 C11 H11 107.5 . . ?
C7 C11 C12 113.21(14) . . ?
C12 C11 H11 107.5 . . ?
C18 C11 C7 112.53(16) . . ?
C18 C11 H11 107.5 . . ?
C18 C11 C12 108.35(15) . . ?
C13 C12 C11 117.19(15) . . ?
C13 C12 H12A 108.0 . . ?
C13 C12 H12B 108.0 . . ?
C11 C12 H12A 108.0 . . ?
C11 C12 H12B 108.0 . . ?
H12A C12 H12B 107.2 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C1 H1 117.0 . . ?
C10 C1 C2 125.97(19) . . ?
C2 C1 H1 117.0 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C3 C2 H2A 110.0 . . ?
C3 C2 H2B 110.0 . . ?
C1 C2 C3 108.31(14) . . ?
C1 C2 H2A 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.4 . . ?
C11 C18 H18A 109.5 . . ?
C11 C18 H18B 109.5 . . ?
C11 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C4 C16 H16A 120.0 . . ?
C4 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
