# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_glo9799
_database_code_depnum_ccdc_archive 'CCDC 2033245'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2020-09-22 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         272.37

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.3649(2)
_cell_length_b                   10.0504(2)
_cell_length_c                   10.2831(3)
_cell_angle_alpha                73.682(2)
_cell_angle_beta                 70.3480(10)
_cell_angle_gamma                86.6350(10)
_cell_volume                     780.74(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5069
_cell_measurement_theta_min      5.6175
_cell_measurement_theta_max      68.2589
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.054
_exptl_crystal_density_diffrn    1.159
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            12248
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_theta_min         4.59
_diffrn_reflns_theta_max         68.30
_diffrn_reflns_theta_full        68.30
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             2832
_reflns_number_gt                2262
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.1895
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0797P)²+0.7796P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.242
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  'APEX3 v2019.1-0'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.2025(2) 0.03577(16) 0.42633(19) 0.0338(4) Uani d . . . 1 . .
O O2 0.0085(2) 0.16574(19) 0.5383(2) 0.0344(5) Uani d . . . 1 . .
H H2 -0.044(5) 0.103(4) 0.555(4) 0.056(11) Uiso d . . . 1 . .
C C1 0.1644(3) 0.1418(2) 0.4636(3) 0.0314(5) Uani d . . . 1 . .
C C2 0.2902(3) 0.2618(2) 0.4231(3) 0.0312(6) Uani d . . . 1 . .
C C3 0.2847(3) 0.3054(3) 0.5566(3) 0.0332(6) Uani d . . . 1 . .
H H3A 0.167955 0.33368 0.600079 0.04 Uiso calc U . R 1 . .
H H3B 0.360914 0.388748 0.523374 0.04 Uiso calc U . R 1 . .
C C4 0.4705(3) 0.2158(3) 0.3484(3) 0.0350(6) Uani d . . . 1 . .
H H4A 0.498625 0.134095 0.416005 0.042 Uiso calc U . R 1 . .
H H4B 0.469717 0.187349 0.263951 0.042 Uiso calc U . R 1 . .
C C5 0.6050(3) 0.3274(3) 0.3005(3) 0.0383(6) Uani d . . . 1 . .
H H5 0.592462 0.411775 0.234661 0.046 Uiso calc U . R 1 . .
C C6 0.7388(3) 0.3193(3) 0.3411(3) 0.0450(7) Uani d . . . 1 . .
H H6A 0.756438 0.236929 0.406852 0.054 Uiso calc U . R 1 . .
H H6B 0.818017 0.395837 0.304911 0.054 Uiso calc U . R 1 . .
C C11 0.3340(3) 0.1987(3) 0.6765(3) 0.0354(6) Uani d . . . 1 . .
H H11 0.441809 0.156205 0.630802 0.042 Uiso calc U . R 1 . .
C C12 0.2020(4) 0.0830(3) 0.7688(3) 0.0425(7) Uani d . . . 1 . .
H H12A 0.194232 0.022471 0.709878 0.051 Uiso calc U . R 1 . .
H H12B 0.089857 0.123895 0.800872 0.051 Uiso calc U . R 1 . .
C C13 0.2425(4) -0.0051(3) 0.9007(3) 0.0465(7) Uani d . . . 1 . .
H H13A 0.147116 -0.072927 0.961384 0.056 Uiso calc U . R 1 . .
H H13B 0.345418 -0.057651 0.869215 0.056 Uiso calc U . R 1 . .
C C14 0.2716(4) 0.0833(3) 0.9889(3) 0.0484(8) Uani d . . . 1 . .
H H14A 0.165071 0.128448 1.029015 0.058 Uiso calc U . R 1 . .
H H14B 0.303594 0.0236 1.070189 0.058 Uiso calc U . R 1 . .
C C15 0.4106(4) 0.1930(3) 0.8975(3) 0.0506(8) Uani d . . . 1 . .
H H15A 0.424116 0.252158 0.955826 0.061 Uiso calc U . R 1 . .
H H15B 0.519418 0.14776 0.864622 0.061 Uiso calc U . R 1 . .
C C16 0.3693(4) 0.2816(3) 0.7692(3) 0.0421(7) Uani d . . . 1 . .
H H16A 0.46553 0.348643 0.708788 0.051 Uiso calc U . R 1 . .
H H16B 0.268353 0.335324 0.803012 0.051 Uiso calc U . R 1 . .
C C21 0.2384(3) 0.3820(3) 0.3140(3) 0.0324(6) Uani d . . . 1 . .
C C22 0.2095(3) 0.5157(3) 0.3287(3) 0.0363(6) Uani d . . . 1 . .
H H22 0.216556 0.536205 0.411352 0.044 Uiso calc U . R 1 . .
C C23 0.1702(3) 0.6197(3) 0.2232(3) 0.0398(6) Uani d . . . 1 . .
H H23 0.153844 0.711089 0.233393 0.048 Uiso calc U . R 1 . .
C C24 0.1548(3) 0.5913(3) 0.1036(3) 0.0372(6) Uani d . . . 1 . .
H H24 0.126017 0.661831 0.032419 0.045 Uiso calc U . R 1 . .
C C25 0.1823(3) 0.4573(3) 0.0900(3) 0.0388(6) Uani d . . . 1 . .
H H25 0.174174 0.436525 0.007789 0.047 Uiso calc U . R 1 . .
C C26 0.2212(3) 0.3546(3) 0.1939(3) 0.0378(6) Uani d . . . 1 . .
H H26 0.23669 0.263293 0.183531 0.045 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.221(3) ?
O2 C1 . 1.320(3) ?
O2 H2 . 0.74(4) ?
C1 C2 . 1.519(3) ?
C2 C3 . 1.540(3) ?
C2 C21 . 1.552(3) ?
C2 C4 . 1.554(3) ?
C3 C11 . 1.545(4) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.494(4) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.311(4) ?
C5 H5 . 0.95 ?
C6 H6A . 0.95 ?
C6 H6B . 0.95 ?
C11 C12 . 1.516(4) ?
C11 C16 . 1.534(4) ?
C11 H11 . 1.0 ?
C12 C13 . 1.529(4) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.516(4) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.511(5) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.505(4) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C26 . 1.392(4) ?
C21 C22 . 1.393(4) ?
C22 C23 . 1.392(4) ?
C22 H22 . 0.95 ?
C23 C24 . 1.386(4) ?
C23 H23 . 0.95 ?
C24 C25 . 1.391(4) ?
C24 H24 . 0.95 ?
C25 C26 . 1.374(4) ?
C25 H25 . 0.95 ?
C26 H26 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 O2 H2 . . 107.(3) ?
O1 C1 O2 . . 123.4(2) ?
O1 C1 C2 . . 123.3(2) ?
O2 C1 C2 . . 113.3(2) ?
C1 C2 C3 . . 111.0(2) ?
C1 C2 C21 . . 106.11(19) ?
C3 C2 C21 . . 111.1(2) ?
C1 C2 C4 . . 108.23(19) ?
C3 C2 C4 . . 110.8(2) ?
C21 C2 C4 . . 109.42(19) ?
C2 C3 C11 . . 118.3(2) ?
C2 C3 H3A . . 107.7 ?
C11 C3 H3A . . 107.7 ?
C2 C3 H3B . . 107.7 ?
C11 C3 H3B . . 107.7 ?
H3A C3 H3B . . 107.1 ?
C5 C4 C2 . . 113.0(2) ?
C5 C4 H4A . . 109.0 ?
C2 C4 H4A . . 109.0 ?
C5 C4 H4B . . 109.0 ?
C2 C4 H4B . . 109.0 ?
H4A C4 H4B . . 107.8 ?
C6 C5 C4 . . 125.8(3) ?
C6 C5 H5 . . 117.1 ?
C4 C5 H5 . . 117.1 ?
C5 C6 H6A . . 120.0 ?
C5 C6 H6B . . 120.0 ?
H6A C6 H6B . . 120.0 ?
C12 C11 C16 . . 110.5(2) ?
C12 C11 C3 . . 115.0(2) ?
C16 C11 C3 . . 106.2(2) ?
C12 C11 H11 . . 108.3 ?
C16 C11 H11 . . 108.3 ?
C3 C11 H11 . . 108.3 ?
C11 C12 C13 . . 112.9(2) ?
C11 C12 H12A . . 109.0 ?
C13 C12 H12A . . 109.0 ?
C11 C12 H12B . . 109.0 ?
C13 C12 H12B . . 109.0 ?
H12A C12 H12B . . 107.8 ?
C14 C13 C12 . . 111.7(2) ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13B . . 109.3 ?
C12 C13 H13B . . 109.3 ?
H13A C13 H13B . . 107.9 ?
C15 C14 C13 . . 110.7(2) ?
C15 C14 H14A . . 109.5 ?
C13 C14 H14A . . 109.5 ?
C15 C14 H14B . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 108.1 ?
C16 C15 C14 . . 110.8(2) ?
C16 C15 H15A . . 109.5 ?
C14 C15 H15A . . 109.5 ?
C16 C15 H15B . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 108.1 ?
C15 C16 C11 . . 113.8(2) ?
C15 C16 H16A . . 108.8 ?
C11 C16 H16A . . 108.8 ?
C15 C16 H16B . . 108.8 ?
C11 C16 H16B . . 108.8 ?
H16A C16 H16B . . 107.7 ?
C26 C21 C22 . . 118.1(2) ?
C26 C21 C2 . . 118.0(2) ?
C22 C21 C2 . . 123.9(2) ?
C23 C22 C21 . . 120.6(2) ?
C23 C22 H22 . . 119.7 ?
C21 C22 H22 . . 119.7 ?
C24 C23 C22 . . 120.7(2) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C23 C24 C25 . . 118.5(2) ?
C23 C24 H24 . . 120.7 ?
C25 C24 H24 . . 120.7 ?
C26 C25 C24 . . 120.8(3) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C25 C26 C21 . . 121.2(2) ?
C25 C26 H26 . . 119.4 ?
C21 C26 H26 . . 119.4 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -129.4(3) ?
O2 C1 C2 C3 . . . . 53.1(3) ?
O1 C1 C2 C21 . . . . 109.8(3) ?
O2 C1 C2 C21 . . . . -67.8(3) ?
O1 C1 C2 C4 . . . . -7.6(3) ?
O2 C1 C2 C4 . . . . 174.9(2) ?
C1 C2 C3 C11 . . . . 62.6(3) ?
C21 C2 C3 C11 . . . . -179.5(2) ?
C4 C2 C3 C11 . . . . -57.7(3) ?
C1 C2 C4 C5 . . . . 178.7(2) ?
C3 C2 C4 C5 . . . . -59.4(3) ?
C21 C2 C4 C5 . . . . 63.4(3) ?
C2 C4 C5 C6 . . . . 121.1(3) ?
C2 C3 C11 C12 . . . . -74.3(3) ?
C2 C3 C11 C16 . . . . 163.2(2) ?
C16 C11 C12 C13 . . . . -50.0(3) ?
C3 C11 C12 C13 . . . . -170.2(2) ?
C11 C12 C13 C14 . . . . 53.7(3) ?
C12 C13 C14 C15 . . . . -56.1(3) ?
C13 C14 C15 C16 . . . . 56.6(3) ?
C14 C15 C16 C11 . . . . -55.3(3) ?
C12 C11 C16 C15 . . . . 51.6(3) ?
C3 C11 C16 C15 . . . . 176.9(2) ?
C1 C2 C21 C26 . . . . -53.2(3) ?
C3 C2 C21 C26 . . . . -173.9(2) ?
C4 C2 C21 C26 . . . . 63.4(3) ?
C1 C2 C21 C22 . . . . 127.3(2) ?
C3 C2 C21 C22 . . . . 6.6(3) ?
C4 C2 C21 C22 . . . . -116.1(2) ?
C26 C21 C22 C23 . . . . -2.2(4) ?
C2 C21 C22 C23 . . . . 177.3(2) ?
C21 C22 C23 C24 . . . . 1.7(4) ?
C22 C23 C24 C25 . . . . -1.1(4) ?
C23 C24 C25 C26 . . . . 1.1(4) ?
C24 C25 C26 C21 . . . . -1.6(4) ?
C22 C21 C26 C25 . . . . 2.1(4) ?
C2 C21 C26 C25 . . . . -177.4(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 2_556 0.74(4) 1.90(4) 2.631(2) 169.(4) ?

####################################################################### 
# 
# 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_glo9874
_database_code_depnum_ccdc_archive 'CCDC 2033247'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2020-09-22 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H21 N O2 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         243.36

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.3005(3)
_cell_length_b                   10.5228(5)
_cell_length_c                   10.9791(5)
_cell_angle_alpha                65.837(3)
_cell_angle_beta                 82.374(3)
_cell_angle_gamma                88.124(4)
_cell_volume                     658.07(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1477
_cell_measurement_theta_min      4.4522
_cell_measurement_theta_max      66.0528
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.096
_exptl_crystal_size_min          0.041
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             264

_exptl_absorpt_coefficient_mu    2.080
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.92

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9493
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_theta_min         4.45
_diffrn_reflns_theta_max         66.63
_diffrn_reflns_theta_full        66.63
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

Structure factors included contributions from the .fab file.

_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_number_total             2315
_reflns_number_gt                1318
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_gt          0.1657
_refine_ls_wR_factor_ref         0.2026
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.036
_refine_ls_number_reflns         2315
_refine_ls_number_parameters     266
_refine_ls_number_restraints     281
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1007P)²+0.1263P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C4 0.7498(5) 0.8142(4) 0.4348(4) 0.0512(9) Uani d . . . 1.0 . .
H H4A 0.634578 0.846698 0.376637 0.061 Uiso calc U . R 1.0 . .
H H4B 0.775253 0.886517 0.467513 0.061 Uiso calc U . R 1.0 . .
C C3 0.6759(5) 0.6812(4) 0.5537(4) 0.0525(9) Uani d U . D 1.0 . .
H H3A 0.795273 0.641968 0.607229 0.063 Uiso calc U . R 1.0 A 1
H H3B 0.630655 0.612073 0.521911 0.063 Uiso calc U . R 1.0 A 1
C C2 0.4857(18) 0.7108(19) 0.6427(12) 0.046(4) Uani d U P D 0.542(6) B 1
C C1 0.298(2) 0.7650(14) 0.5610(16) 0.041(3) Uani d U P D 0.542(6) B 1
O O1 0.207(2) 0.8679(12) 0.5527(15) 0.059(3) Uani d U P D 0.542(6) B 1
O O2 0.244(3) 0.6872(16) 0.500(2) 0.049(3) Uani d U P D 0.542(6) B 1
H H2 0.23491 0.60322 0.555196 0.073 Uiso calc U P R 0.542(6) B 1
C C5 0.545(2) 0.8006(15) 0.7126(18) 0.045(3) Uani d U P D 0.542(6) B 1
H H5A 0.557943 0.898697 0.645765 0.054 Uiso calc U P R 0.542(6) B 1
H H5B 0.425944 0.794516 0.783243 0.054 Uiso calc U P R 0.542(6) B 1
C C6 0.7370(11) 0.7675(7) 0.7729(7) 0.059(2) Uani d U P D 0.542(6) B 1
H H6 0.868862 0.783004 0.715195 0.071 Uiso calc U P R 0.542(6) B 1
C C7 0.7442(14) 0.7163(9) 0.9044(8) 0.080(3) Uani d U P D 0.542(6) B 1
H H7A 0.615271 0.699486 0.964971 0.096 Uiso calc U P R 0.542(6) B 1
H H7B 0.87823 0.696335 0.93821 0.096 Uiso calc U P R 0.542(6) B 1
C C8 0.409(3) 0.5674(18) 0.754(2) 0.084(7) Uani d U P D 0.542(6) B 1
H H8A 0.368956 0.506694 0.71205 0.126 Uiso calc U P R 0.542(6) B 1
H H8B 0.524527 0.525211 0.807929 0.126 Uiso calc U P R 0.542(6) B 1
H H8C 0.284357 0.579274 0.811497 0.126 Uiso calc U P R 0.542(6) B 1
C C2A 0.475(2) 0.688(2) 0.6478(13) 0.046(4) Uani d U P D 0.458(6) B 2
C C1A 0.288(3) 0.7337(18) 0.563(2) 0.056(5) Uani d U P D 0.458(6) B 2
O O1A 0.227(4) 0.655(2) 0.518(3) 0.066(5) Uani d U P D 0.458(6) B 2
O O2A 0.215(3) 0.8563(17) 0.531(2) 0.092(5) Uani d U P D 0.458(6) B 2
H H2A 0.16405 0.865561 0.601918 0.137 Uiso calc U P R 0.458(6) B 2
C C5A 0.428(3) 0.5461(19) 0.764(2) 0.053(4) Uani d U P D 0.458(6) B 2
H H501 0.431999 0.474241 0.727451 0.063 Uiso calc U P R 0.458(6) B 2
H H502 0.541809 0.525933 0.822842 0.063 Uiso calc U P R 0.458(6) B 2
C C6A 0.2273(16) 0.5358(12) 0.8430(10) 0.088(3) Uani d U P D 0.458(6) B 2
H H6A 0.111589 0.589804 0.802829 0.105 Uiso calc U P R 0.458(6) B 2
C C7A 0.200(2) 0.4510(13) 0.9729(11) 0.105(4) Uani d U P D 0.458(6) B 2
H H701 0.315263 0.396788 1.013348 0.126 Uiso calc U P R 0.458(6) B 2
H H702 0.064757 0.44449 1.025361 0.126 Uiso calc U P R 0.458(6) B 2
C C8A 0.514(4) 0.803(2) 0.695(3) 0.070(6) Uani d U P D 0.458(6) B 2
H H801 0.54331 0.891801 0.616541 0.104 Uiso calc U P R 0.458(6) B 2
H H802 0.386257 0.811046 0.752817 0.104 Uiso calc U P R 0.458(6) B 2
H H803 0.636665 0.779284 0.745751 0.104 Uiso calc U P R 0.458(6) B 2
N N1 0.9486(4) 0.7986(3) 0.3532(3) 0.0513(7) Uani d U . D 1.0 . .
C C11 0.894(2) 0.6978(13) 0.2965(14) 0.052(3) Uani d U P D 0.52(2) C 1
H H11C 0.78161 0.737649 0.236857 0.063 Uiso calc U P R 0.52(2) C 1
H H11D 0.834868 0.610176 0.371002 0.063 Uiso calc U P R 0.52(2) C 1
C C12 1.091(2) 0.6656(11) 0.2165(10) 0.055(3) Uani d U P D 0.52(2) C 1
H H12C 1.047766 0.598209 0.181925 0.066 Uiso calc U P R 0.52(2) C 1
H H12D 1.198207 0.620766 0.278097 0.066 Uiso calc U P R 0.52(2) C 1
S S1 1.2123(14) 0.8165(8) 0.0774(4) 0.0692(15) Uani d U P D 0.52(2) C 1
C C13 1.244(2) 0.9148(14) 0.1749(11) 0.061(3) Uani d U P D 0.52(2) C 1
H H13C 1.341691 0.865481 0.242278 0.073 Uiso calc U P R 0.52(2) C 1
H H13D 1.310091 1.007041 0.114791 0.073 Uiso calc U P R 0.52(2) C 1
C C14 1.028(3) 0.9347(12) 0.2472(18) 0.058(4) Uani d U P D 0.52(2) C 1
H H14C 1.04631 1.0014 0.287911 0.07 Uiso calc U P R 0.52(2) C 1
H H14D 0.923995 0.972993 0.18191 0.07 Uiso calc U P R 0.52(2) C 1
C C11A 0.943(2) 0.7156(17) 0.2733(17) 0.065(4) Uani d U P D 0.48(2) C 2
H H11A 0.849595 0.760686 0.202279 0.078 Uiso calc U P R 0.48(2) C 2
H H11B 0.881969 0.62158 0.332298 0.078 Uiso calc U P R 0.48(2) C 2
C C12A 1.167(2) 0.7029(14) 0.2090(12) 0.073(4) Uani d U P D 0.48(2) C 2
H H12A 1.162936 0.633195 0.170169 0.087 Uiso calc U P R 0.48(2) C 2
H H12B 1.263059 0.668139 0.279669 0.087 Uiso calc U P R 0.48(2) C 2
S S1A 1.2763(13) 0.8638(12) 0.0794(5) 0.0803(18) Uani d U P D 0.48(2) C 2
C C13A 1.247(3) 0.9628(18) 0.1802(14) 0.075(4) Uani d U P D 0.48(2) C 2
H H13A 1.358176 0.93479 0.241476 0.09 Uiso calc U P R 0.48(2) C 2
H H13B 1.271649 1.062707 0.120381 0.09 Uiso calc U P R 0.48(2) C 2
C C14A 1.028(3) 0.9440(13) 0.264(2) 0.061(4) Uani d U P D 0.48(2) C 2
H H14A 1.030425 0.996174 0.320973 0.073 Uiso calc U P R 0.48(2) C 2
H H14B 0.921235 0.988515 0.201232 0.073 Uiso calc U P R 0.48(2) C 2


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C4 N1 . 1.486(4) ?
C4 C3 . 1.505(5) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C3 C2A . 1.544(11) ?
C3 C2 . 1.550(10) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C2 C5 . 1.522(14) ?
C2 C1 . 1.533(10) ?
C2 C8 . 1.543(15) ?
C1 O1 . 1.184(13) ?
C1 O2 . 1.323(14) ?
O2 H2 . 0.84 ?
C5 C6 . 1.418(17) ?
C5 H5A . 0.99 ?
C5 H5B . 0.99 ?
C6 C7 . 1.326(10) ?
C6 H6 . 0.95 ?
C7 H7A . 0.95 ?
C7 H7B . 0.95 ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C2A C5A . 1.522(18) ?
C2A C8A . 1.535(19) ?
C2A C1A . 1.540(12) ?
C1A O1A . 1.214(18) ?
C1A O2A . 1.278(18) ?
O2A H2A . 0.84 ?
C5A C6A . 1.412(18) ?
C5A H501 . 0.99 ?
C5A H502 . 0.99 ?
C6A C7A . 1.328(13) ?
C6A H6A . 0.95 ?
C7A H701 . 0.95 ?
C7A H702 . 0.95 ?
C8A H801 . 0.98 ?
C8A H802 . 0.98 ?
C8A H803 . 0.98 ?
N1 C11A . 1.474(11) ?
N1 C14 . 1.478(11) ?
N1 C14A . 1.498(11) ?
N1 C11 . 1.503(10) ?
C11 C12 . 1.534(11) ?
C11 H11C . 0.99 ?
C11 H11D . 0.99 ?
C12 S1 . 1.796(9) ?
C12 H12C . 0.99 ?
C12 H12D . 0.99 ?
S1 C13 . 1.798(10) ?
C13 C14 . 1.534(12) ?
C13 H13C . 0.99 ?
C13 H13D . 0.99 ?
C14 H14C . 0.99 ?
C14 H14D . 0.99 ?
C11A C12A . 1.520(12) ?
C11A H11A . 0.99 ?
C11A H11B . 0.99 ?
C12A S1A . 1.791(10) ?
C12A H12A . 0.99 ?
C12A H12B . 0.99 ?
S1A C13A . 1.794(10) ?
C13A C14A . 1.524(12) ?
C13A H13A . 0.99 ?
C13A H13B . 0.99 ?
C14A H14A . 0.99 ?
C14A H14B . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C4 C3 . . 113.2(3) ?
N1 C4 H4A . . 108.9 ?
C3 C4 H4A . . 108.9 ?
N1 C4 H4B . . 108.9 ?
C3 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.8 ?
C4 C3 C2A . . 117.1(8) ?
C4 C3 C2 . . 109.7(7) ?
C4 C3 H3A . . 109.7 ?
C2 C3 H3A . . 109.7 ?
C4 C3 H3B . . 109.7 ?
C2 C3 H3B . . 109.7 ?
H3A C3 H3B . . 108.2 ?
C5 C2 C1 . . 114.3(12) ?
C5 C2 C8 . . 107.3(11) ?
C1 C2 C8 . . 105.3(13) ?
C5 C2 C3 . . 114.1(11) ?
C1 C2 C3 . . 109.3(8) ?
C8 C2 C3 . . 105.8(13) ?
O1 C1 O2 . . 122.3(11) ?
O1 C1 C2 . . 122.9(13) ?
O2 C1 C2 . . 114.8(13) ?
C1 O2 H2 . . 109.5 ?
C6 C5 C2 . . 116.6(10) ?
C6 C5 H5A . . 108.1 ?
C2 C5 H5A . . 108.1 ?
C6 C5 H5B . . 108.1 ?
C2 C5 H5B . . 108.1 ?
H5A C5 H5B . . 107.3 ?
C7 C6 C5 . . 124.3(9) ?
C7 C6 H6 . . 117.8 ?
C5 C6 H6 . . 117.8 ?
C6 C7 H7A . . 120.0 ?
C6 C7 H7B . . 120.0 ?
H7A C7 H7B . . 120.0 ?
C2 C8 H8A . . 109.5 ?
C2 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C2 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C5A C2A C8A . . 112.8(12) ?
C5A C2A C1A . . 111.2(16) ?
C8A C2A C1A . . 107.4(15) ?
C5A C2A C3 . . 109.9(12) ?
C8A C2A C3 . . 108.1(15) ?
C1A C2A C3 . . 107.2(11) ?
O1A C1A O2A . . 121.8(15) ?
O1A C1A C2A . . 118.3(18) ?
O2A C1A C2A . . 119.6(17) ?
C1A O2A H2A . . 109.5 ?
C6A C5A C2A . . 113.9(14) ?
C6A C5A H501 . . 108.8 ?
C2A C5A H501 . . 108.8 ?
C6A C5A H502 . . 108.8 ?
C2A C5A H502 . . 108.8 ?
H501 C5A H502 . . 107.7 ?
C7A C6A C5A . . 120.4(13) ?
C7A C6A H6A . . 119.8 ?
C5A C6A H6A . . 119.8 ?
C6A C7A H701 . . 120.0 ?
C6A C7A H702 . . 120.0 ?
H701 C7A H702 . . 120.0 ?
C2A C8A H801 . . 109.5 ?
C2A C8A H802 . . 109.5 ?
H801 C8A H802 . . 109.5 ?
C2A C8A H803 . . 109.5 ?
H801 C8A H803 . . 109.5 ?
H802 C8A H803 . . 109.5 ?
C11A N1 C4 . . 119.7(6) ?
C14 N1 C4 . . 111.2(6) ?
C11A N1 C14A . . 110.2(10) ?
C4 N1 C14A . . 105.5(6) ?
C14 N1 C11 . . 112.5(9) ?
C4 N1 C11 . . 106.2(5) ?
N1 C11 C12 . . 111.4(8) ?
N1 C11 H11C . . 109.3 ?
C12 C11 H11C . . 109.3 ?
N1 C11 H11D . . 109.3 ?
C12 C11 H11D . . 109.3 ?
H11C C11 H11D . . 108.0 ?
C11 C12 S1 . . 113.8(7) ?
C11 C12 H12C . . 108.8 ?
S1 C12 H12C . . 108.8 ?
C11 C12 H12D . . 108.8 ?
S1 C12 H12D . . 108.8 ?
H12C C12 H12D . . 107.7 ?
C12 S1 C13 . . 95.6(5) ?
C14 C13 S1 . . 111.4(10) ?
C14 C13 H13C . . 109.3 ?
S1 C13 H13C . . 109.3 ?
C14 C13 H13D . . 109.3 ?
S1 C13 H13D . . 109.3 ?
H13C C13 H13D . . 108.0 ?
N1 C14 C13 . . 109.0(10) ?
N1 C14 H14C . . 109.9 ?
C13 C14 H14C . . 109.9 ?
N1 C14 H14D . . 109.9 ?
C13 C14 H14D . . 109.9 ?
H14C C14 H14D . . 108.3 ?
N1 C11A C12A . . 110.5(10) ?
N1 C11A H11A . . 109.5 ?
C12A C11A H11A . . 109.5 ?
N1 C11A H11B . . 109.5 ?
C12A C11A H11B . . 109.5 ?
H11A C11A H11B . . 108.1 ?
C11A C12A S1A . . 113.4(9) ?
C11A C12A H12A . . 108.9 ?
S1A C12A H12A . . 108.9 ?
C11A C12A H12B . . 108.9 ?
S1A C12A H12B . . 108.9 ?
H12A C12A H12B . . 107.7 ?
C12A S1A C13A . . 96.6(6) ?
C14A C13A S1A . . 113.7(11) ?
C14A C13A H13A . . 108.8 ?
S1A C13A H13A . . 108.8 ?
C14A C13A H13B . . 108.8 ?
S1A C13A H13B . . 108.8 ?
H13A C13A H13B . . 107.7 ?
N1 C14A C13A . . 117.9(12) ?
N1 C14A H14A . . 107.8 ?
C13A C14A H14A . . 107.8 ?
N1 C14A H14B . . 107.8 ?
C13A C14A H14B . . 107.8 ?
H14A C14A H14B . . 107.2 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C4 C3 C2A . . . . 177.8(8) ?
N1 C4 C3 C2 . . . . 172.9(6) ?
C4 C3 C2 C5 . . . . -67.3(11) ?
C4 C3 C2 C1 . . . . 62.0(13) ?
C4 C3 C2 C8 . . . . 175.0(10) ?
C5 C2 C1 O1 . . . . 0.(2) ?
C8 C2 C1 O1 . . . . 118.(2) ?
C3 C2 C1 O1 . . . . -129.2(17) ?
C5 C2 C1 O2 . . . . -179.6(16) ?
C8 C2 C1 O2 . . . . -62.1(19) ?
C3 C2 C1 O2 . . . . 51.(2) ?
C1 C2 C5 C6 . . . . -170.9(12) ?
C8 C2 C5 C6 . . . . 72.7(15) ?
C3 C2 C5 C6 . . . . -44.1(17) ?
C2 C5 C6 C7 . . . . -112.4(14) ?
C4 C3 C2A C5A . . . . -178.3(11) ?
C4 C3 C2A C8A . . . . -54.9(13) ?
C4 C3 C2A C1A . . . . 60.7(16) ?
C5A C2A C1A O1A . . . . -54.(3) ?
C8A C2A C1A O1A . . . . -178.(2) ?
C3 C2A C1A O1A . . . . 66.(3) ?
C5A C2A C1A O2A . . . . 132.(2) ?
C8A C2A C1A O2A . . . . 8.(3) ?
C3 C2A C1A O2A . . . . -108.(2) ?
C8A C2A C5A C6A . . . . 69.(2) ?
C1A C2A C5A C6A . . . . -51.(2) ?
C3 C2A C5A C6A . . . . -170.0(15) ?
C2A C5A C6A C7A . . . . -150.3(16) ?
C3 C4 N1 C11A . . . . 69.3(9) ?
C3 C4 N1 C14 . . . . -173.6(11) ?
C3 C4 N1 C14A . . . . -165.9(12) ?
C3 C4 N1 C11 . . . . 63.7(7) ?
C14 N1 C11 C12 . . . . 61.6(13) ?
C4 N1 C11 C12 . . . . -176.5(8) ?
N1 C11 C12 S1 . . . . -59.2(12) ?
C11 C12 S1 C13 . . . . 54.0(9) ?
C12 S1 C13 C14 . . . . -58.2(10) ?
C4 N1 C14 C13 . . . . 174.7(10) ?
C11 N1 C14 C13 . . . . -66.2(17) ?
S1 C13 C14 N1 . . . . 68.6(16) ?
C4 N1 C11A C12A . . . . -174.7(8) ?
C14A N1 C11A C12A . . . . 62.7(16) ?
N1 C11A C12A S1A . . . . -68.8(14) ?
C11A C12A S1A C13A . . . . 55.8(11) ?
C12A S1A C13A C14A . . . . -46.7(14) ?
C11A N1 C14A C13A . . . . -57.(2) ?
C4 N1 C14A C13A . . . . 172.2(15) ?
S1A C13A C14A N1 . . . . 53.(2) ?

####################################################################### 
# 
# 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_glo9876
_database_code_depnum_ccdc_archive 'CCDC 2033246'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2020-09-22 deposited with the CCDC.	2021-01-07 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2019.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H26 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         322.43

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5885(4)
_cell_length_b                   8.3629(3)
_cell_length_c                   20.6387(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.927(2)
_cell_angle_gamma                90
_cell_volume                     1800.21(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6556
_cell_measurement_theta_min      4.4183
_cell_measurement_theta_max      66.5678
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.077
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696

_exptl_absorpt_coefficient_mu    0.578
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 Bruker AXS area detector scaling and absorption correction.
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu Ims'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON III Diffractometer'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            26566
_diffrn_reflns_av_R_equivalents  0.1045
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_theta_min         4.42
_diffrn_reflns_theta_max         66.70
_diffrn_reflns_theta_full        66.70
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24

_refine_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.

Structure factors included contributions from the .fab file.

_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_number_total             3174
_reflns_number_gt                2277
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_gt          0.1056
_refine_ls_wR_factor_ref         0.1201
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         3174
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.7326P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.214
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'APEX3 v2019.1-0'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 958)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.98621(12) 0.18923(16) 0.52300(7) 0.0277(3) Uani d . . . 1 . .
O O2 0.83052(13) 0.00727(15) 0.49637(7) 0.0281(3) Uani d . . . 1 . .
H H2 0.903(3) -0.063(4) 0.4890(15) 0.077(9) Uiso d . . . 1 . .
C C1 0.76864(17) 0.2575(2) 0.53563(9) 0.0245(4) Uani d . . . 1 . .
C C2 0.87323(18) 0.1483(2) 0.51858(9) 0.0247(4) Uani d . . . 1 . .
C C3 0.69081(18) 0.3132(2) 0.46848(9) 0.0257(4) Uani d . . . 1 . .
H H3A 0.648675 0.2184 0.445474 0.031 Uiso calc U . R 1 . .
H H3B 0.622203 0.386265 0.477336 0.031 Uiso calc U . R 1 . .
C C4 0.82877(18) 0.4055(2) 0.57467(10) 0.0263(4) Uani d . . . 1 . .
H H4A 0.875875 0.369623 0.617864 0.032 Uiso calc U . R 1 . .
H H4B 0.891524 0.455254 0.550421 0.032 Uiso calc U . R 1 . .
C C5 0.7317(2) 0.5288(2) 0.58564(10) 0.0321(5) Uani d . . . 1 . .
H H5 0.661685 0.495395 0.605625 0.038 Uiso calc U . R 1 . .
C C6 0.7374(3) 0.6799(3) 0.56935(11) 0.0444(6) Uani d . . . 1 . .
H H6A 0.806189 0.717079 0.549276 0.053 Uiso calc U . R 1 . .
H H6B 0.672811 0.752176 0.577614 0.053 Uiso calc U . R 1 . .
C C11 0.76778(19) 0.3989(2) 0.42147(9) 0.0278(4) Uani d . . . 1 . .
H H11 0.847755 0.442638 0.448535 0.033 Uiso calc U . R 1 . .
C C12 0.8072(2) 0.2894(3) 0.36906(10) 0.0330(5) Uani d . . . 1 . .
H H12A 0.859412 0.200024 0.390765 0.04 Uiso calc U . R 1 . .
H H12B 0.729465 0.243564 0.341872 0.04 Uiso calc U . R 1 . .
C C13 0.8843(2) 0.3801(3) 0.32481(10) 0.0330(5) Uani d . . . 1 . .
H H13A 0.966842 0.414587 0.351206 0.04 Uiso calc U . R 1 . .
H H13B 0.90344 0.307415 0.289909 0.04 Uiso calc U . R 1 . .
C C14 0.8133(2) 0.5257(3) 0.29317(11) 0.0442(6) Uani d . . . 1 . .
H H14A 0.738156 0.49042 0.260917 0.053 Uiso calc U . R 1 . .
H H14B 0.870504 0.587143 0.269168 0.053 Uiso calc U . R 1 . .
C C15 0.7682(3) 0.6336(3) 0.34436(12) 0.0499(6) Uani d . . . 1 . .
H H15A 0.843536 0.682902 0.372304 0.06 Uiso calc U . R 1 . .
H H15B 0.714285 0.720612 0.321809 0.06 Uiso calc U . R 1 . .
C C16 0.6914(2) 0.5392(3) 0.38751(11) 0.0408(6) Uani d . . . 1 . .
H H16A 0.666384 0.611149 0.421232 0.049 Uiso calc U . R 1 . .
H H16B 0.611942 0.498487 0.360051 0.049 Uiso calc U . R 1 . .
C C21 0.68579(17) 0.1636(2) 0.57721(9) 0.0242(4) Uani d . . . 1 . .
C C22 0.55485(18) 0.1615(2) 0.55988(10) 0.0283(4) Uani d . . . 1 . .
H H22 0.516101 0.215766 0.521065 0.034 Uiso calc U . R 1 . .
C C23 0.47542(19) 0.0810(2) 0.59809(11) 0.0325(5) Uani d . . . 1 . .
H H23 0.384894 0.082829 0.585044 0.039 Uiso calc U . R 1 . .
C C24 0.5290(2) 0.0013(2) 0.65334(11) 0.0335(5) Uani d . . . 1 . .
H H24 0.475342 -0.052863 0.678634 0.04 Uiso calc U . R 1 . .
C C25 0.66335(19) -0.0024(2) 0.67377(10) 0.0295(5) Uani d . . . 1 . .
C C26 0.7190(2) -0.0904(3) 0.73031(11) 0.0382(5) Uani d . . . 1 . .
H H26 0.664649 -0.145365 0.754988 0.046 Uiso calc U . R 1 . .
C C27 0.8485(2) -0.0980(3) 0.75009(11) 0.0390(5) Uani d . . . 1 . .
H H27 0.884139 -0.158515 0.787781 0.047 Uiso calc U . R 1 . .
C C29 0.87838(19) 0.0707(2) 0.65912(10) 0.0290(5) Uani d . . . 1 . .
H H29 0.934938 0.125667 0.635735 0.035 Uiso calc U . R 1 . .
C C30 0.74393(18) 0.0802(2) 0.63601(10) 0.0262(4) Uani d . . . 1 . .
C C28 0.9286(2) -0.0149(2) 0.71382(10) 0.0349(5) Uani d . . . 1 . .
H H28 1.01887 -0.018447 0.727625 0.042 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . 1.232(2) ?
O2 C2 . 1.317(2) ?
O2 H2 . 1.00(3) ?
C1 C2 . 1.523(3) ?
C1 C21 . 1.543(3) ?
C1 C4 . 1.552(3) ?
C1 C3 . 1.557(3) ?
C3 C11 . 1.546(3) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 C5 . 1.501(3) ?
C4 H4A . 0.99 ?
C4 H4B . 0.99 ?
C5 C6 . 1.312(3) ?
C5 H5 . 0.95 ?
C6 H6A . 0.95 ?
C6 H6B . 0.95 ?
C11 C16 . 1.525(3) ?
C11 C12 . 1.529(3) ?
C11 H11 . 1.0 ?
C12 C13 . 1.527(3) ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 C14 . 1.518(3) ?
C13 H13A . 0.99 ?
C13 H13B . 0.99 ?
C14 C15 . 1.527(3) ?
C14 H14A . 0.99 ?
C14 H14B . 0.99 ?
C15 C16 . 1.526(3) ?
C15 H15A . 0.99 ?
C15 H15B . 0.99 ?
C16 H16A . 0.99 ?
C16 H16B . 0.99 ?
C21 C22 . 1.371(3) ?
C21 C30 . 1.443(3) ?
C22 C23 . 1.418(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.358(3) ?
C23 H23 . 0.95 ?
C24 C25 . 1.413(3) ?
C24 H24 . 0.95 ?
C25 C26 . 1.419(3) ?
C25 C30 . 1.429(3) ?
C26 C27 . 1.363(3) ?
C26 H26 . 0.95 ?
C27 C28 . 1.408(3) ?
C27 H27 . 0.95 ?
C29 C28 . 1.365(3) ?
C29 C30 . 1.424(3) ?
C29 H29 . 0.95 ?
C28 H28 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O2 H2 . . 110.6(17) ?
C2 C1 C21 . . 109.22(15) ?
C2 C1 C4 . . 110.40(15) ?
C21 C1 C4 . . 109.79(15) ?
C2 C1 C3 . . 105.55(15) ?
C21 C1 C3 . . 112.51(15) ?
C4 C1 C3 . . 109.29(15) ?
O1 C2 O2 . . 123.04(17) ?
O1 C2 C1 . . 123.48(17) ?
O2 C2 C1 . . 113.44(16) ?
C11 C3 C1 . . 116.22(15) ?
C11 C3 H3A . . 108.2 ?
C1 C3 H3A . . 108.2 ?
C11 C3 H3B . . 108.2 ?
C1 C3 H3B . . 108.2 ?
H3A C3 H3B . . 107.4 ?
C5 C4 C1 . . 113.32(16) ?
C5 C4 H4A . . 108.9 ?
C1 C4 H4A . . 108.9 ?
C5 C4 H4B . . 108.9 ?
C1 C4 H4B . . 108.9 ?
H4A C4 H4B . . 107.7 ?
C6 C5 C4 . . 124.1(2) ?
C6 C5 H5 . . 118.0 ?
C4 C5 H5 . . 118.0 ?
C5 C6 H6A . . 120.0 ?
C5 C6 H6B . . 120.0 ?
H6A C6 H6B . . 120.0 ?
C16 C11 C12 . . 108.86(17) ?
C16 C11 C3 . . 110.45(17) ?
C12 C11 C3 . . 113.84(16) ?
C16 C11 H11 . . 107.8 ?
C12 C11 H11 . . 107.8 ?
C3 C11 H11 . . 107.8 ?
C13 C12 C11 . . 111.41(17) ?
C13 C12 H12A . . 109.3 ?
C11 C12 H12A . . 109.3 ?
C13 C12 H12B . . 109.3 ?
C11 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C14 C13 C12 . . 112.30(18) ?
C14 C13 H13A . . 109.1 ?
C12 C13 H13A . . 109.1 ?
C14 C13 H13B . . 109.1 ?
C12 C13 H13B . . 109.1 ?
H13A C13 H13B . . 107.9 ?
C13 C14 C15 . . 111.53(18) ?
C13 C14 H14A . . 109.3 ?
C15 C14 H14A . . 109.3 ?
C13 C14 H14B . . 109.3 ?
C15 C14 H14B . . 109.3 ?
H14A C14 H14B . . 108.0 ?
C16 C15 C14 . . 111.1(2) ?
C16 C15 H15A . . 109.4 ?
C14 C15 H15A . . 109.4 ?
C16 C15 H15B . . 109.4 ?
C14 C15 H15B . . 109.4 ?
H15A C15 H15B . . 108.0 ?
C11 C16 C15 . . 111.86(19) ?
C11 C16 H16A . . 109.2 ?
C15 C16 H16A . . 109.2 ?
C11 C16 H16B . . 109.2 ?
C15 C16 H16B . . 109.2 ?
H16A C16 H16B . . 107.9 ?
C22 C21 C30 . . 118.61(18) ?
C22 C21 C1 . . 120.51(17) ?
C30 C21 C1 . . 120.86(16) ?
C21 C22 C23 . . 122.08(19) ?
C21 C22 H22 . . 119.0 ?
C23 C22 H22 . . 119.0 ?
C24 C23 C22 . . 119.88(19) ?
C24 C23 H23 . . 120.1 ?
C22 C23 H23 . . 120.1 ?
C23 C24 C25 . . 120.98(19) ?
C23 C24 H24 . . 119.5 ?
C25 C24 H24 . . 119.5 ?
C24 C25 C26 . . 120.70(19) ?
C24 C25 C30 . . 119.48(18) ?
C26 C25 C30 . . 119.80(19) ?
C27 C26 C25 . . 121.6(2) ?
C27 C26 H26 . . 119.2 ?
C25 C26 H26 . . 119.2 ?
C26 C27 C28 . . 119.0(2) ?
C26 C27 H27 . . 120.5 ?
C28 C27 H27 . . 120.5 ?
C28 C29 C30 . . 122.0(2) ?
C28 C29 H29 . . 119.0 ?
C30 C29 H29 . . 119.0 ?
C29 C30 C25 . . 116.57(18) ?
C29 C30 C21 . . 124.45(18) ?
C25 C30 C21 . . 118.97(17) ?
C29 C28 C27 . . 121.0(2) ?
C29 C28 H28 . . 119.5 ?
C27 C28 H28 . . 119.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C21 C1 C2 O1 . . . . -134.91(18) ?
C4 C1 C2 O1 . . . . -14.1(2) ?
C3 C1 C2 O1 . . . . 103.9(2) ?
C21 C1 C2 O2 . . . . 47.3(2) ?
C4 C1 C2 O2 . . . . 168.15(16) ?
C3 C1 C2 O2 . . . . -73.85(19) ?
C2 C1 C3 C11 . . . . -57.2(2) ?
C21 C1 C3 C11 . . . . -176.19(15) ?
C4 C1 C3 C11 . . . . 61.6(2) ?
C2 C1 C4 C5 . . . . 172.57(16) ?
C21 C1 C4 C5 . . . . -67.0(2) ?
C3 C1 C4 C5 . . . . 56.9(2) ?
C1 C4 C5 C6 . . . . -125.9(2) ?
C1 C3 C11 C16 . . . . -139.83(18) ?
C1 C3 C11 C12 . . . . 97.4(2) ?
C16 C11 C12 C13 . . . . 57.1(2) ?
C3 C11 C12 C13 . . . . -179.24(16) ?
C11 C12 C13 C14 . . . . -55.4(2) ?
C12 C13 C14 C15 . . . . 52.6(3) ?
C13 C14 C15 C16 . . . . -52.9(3) ?
C12 C11 C16 C15 . . . . -58.3(2) ?
C3 C11 C16 C15 . . . . 176.01(18) ?
C14 C15 C16 C11 . . . . 56.8(3) ?
C2 C1 C21 C22 . . . . -128.64(18) ?
C4 C1 C21 C22 . . . . 110.18(19) ?
C3 C1 C21 C22 . . . . -11.8(2) ?
C2 C1 C21 C30 . . . . 53.1(2) ?
C4 C1 C21 C30 . . . . -68.0(2) ?
C3 C1 C21 C30 . . . . 169.99(16) ?
C30 C21 C22 C23 . . . . 0.4(3) ?
C1 C21 C22 C23 . . . . -177.88(17) ?
C21 C22 C23 C24 . . . . -0.7(3) ?
C22 C23 C24 C25 . . . . 0.3(3) ?
C23 C24 C25 C26 . . . . -177.9(2) ?
C23 C24 C25 C30 . . . . 0.5(3) ?
C24 C25 C26 C27 . . . . 178.7(2) ?
C30 C25 C26 C27 . . . . 0.3(3) ?
C25 C26 C27 C28 . . . . 0.7(3) ?
C28 C29 C30 C25 . . . . 1.1(3) ?
C28 C29 C30 C21 . . . . -177.53(19) ?
C24 C25 C30 C29 . . . . -179.60(18) ?
C26 C25 C30 C29 . . . . -1.2(3) ?
C24 C25 C30 C21 . . . . -0.9(3) ?
C26 C25 C30 C21 . . . . 177.53(18) ?
C22 C21 C30 C29 . . . . 179.04(18) ?
C1 C21 C30 C29 . . . . -2.7(3) ?
C22 C21 C30 C25 . . . . 0.4(3) ?
C1 C21 C30 C25 . . . . 178.68(17) ?
C30 C29 C28 C27 . . . . -0.1(3) ?
C26 C27 C28 C29 . . . . -0.8(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2 O1 3_756 1.00(3) 1.63(3) 2.6255(18) 175.(3) ?

