# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_mo_20211128_0m
_database_code_depnum_ccdc_archive 'CCDC 2144826'
loop_
_audit_author_name
_audit_author_address
'Xiaofeng Chen'
;National Research Institute for Family Planning
China
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-28
_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         'C23 H30 O4, C7 H6 O3'
_chemical_formula_sum            'C30 H36 O7'
_chemical_formula_weight         508.59
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.9467(11)
_cell_length_b                   11.0450(14)
_cell_length_c                   11.7816(13)
_cell_angle_alpha                90
_cell_angle_beta                 112.707(4)
_cell_angle_gamma                90
_cell_volume                     1314.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6182
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.377
_cell_measurement_theta_min      2.629
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1219 before and 0.0630 after correction. The Ratio of minimum to maximum transmission is 0.8742. 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    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.15
_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  0.0466
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15274
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.403
_diffrn_reflns_theta_min         1.874
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                4503
_reflns_number_total             5342
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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         0.192
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.7(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5342
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.049
_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)+(0.0348P)²+0.2304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0951
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.7(12)
 -0.7(12)
2. 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
3. Restrained distances
 O5-H5 = O6-H6
 0.87 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C26(H26), C27(H27), C29(H29), C30(H30)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4502(2) 0.5772(2) 0.65167(18) 0.0380(6) Uani 1 1 d . . . . .
O2 O -0.2227(2) 0.6525(2) -0.4120(2) 0.0432(6) Uani 1 1 d . . . . .
O3 O 0.02554(17) 0.44546(18) -0.24541(16) 0.0250(4) Uani 1 1 d . . . . .
O4 O -0.0225(2) 0.4449(2) -0.44796(18) 0.0389(5) Uani 1 1 d . . . . .
C1 C 0.1765(3) 0.5130(3) 0.3646(3) 0.0358(8) Uani 1 1 d . . . . .
H1A H 0.217687 0.435041 0.357676 0.043 Uiso 1 1 calc R . . . .
H1B H 0.079887 0.499887 0.337594 0.043 Uiso 1 1 calc R . . . .
C2 C 0.2332(3) 0.5552(3) 0.4986(3) 0.0373(8) Uani 1 1 d . . . . .
H2A H 0.183850 0.627549 0.506952 0.045 Uiso 1 1 calc R . . . .
H2B H 0.220785 0.490591 0.551402 0.045 Uiso 1 1 calc R . . . .
C3 C 0.3766(3) 0.5854(3) 0.5419(3) 0.0302(7) Uani 1 1 d . . . . .
C4 C 0.4263(3) 0.6277(3) 0.4507(3) 0.0295(7) Uani 1 1 d . . . . .
H4 H 0.517335 0.648169 0.477207 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3488(3) 0.6389(3) 0.3305(3) 0.0240(6) Uani 1 1 d . . . . .
C6 C 0.4025(3) 0.6873(3) 0.2429(3) 0.0251(6) Uani 1 1 d . . . . .
C7 C 0.3235(3) 0.7029(3) 0.1244(3) 0.0259(6) Uani 1 1 d . . . . .
H7 H 0.361231 0.737107 0.071343 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1793(3) 0.6698(3) 0.0699(2) 0.0222(6) Uani 1 1 d . . . . .
H8 H 0.126957 0.742886 0.073486 0.027 Uiso 1 1 calc R . . . .
C9 C 0.1503(3) 0.5690(3) 0.1457(2) 0.0223(6) Uani 1 1 d . . . . .
H9 H 0.200247 0.495296 0.139317 0.027 Uiso 1 1 calc R . . . .
C10 C 0.2025(3) 0.6066(3) 0.2820(3) 0.0246(6) Uani 1 1 d . . . . .
H10 H 0.153738 0.681691 0.286872 0.030 Uiso 1 1 calc R . . . .
C11 C 0.0028(3) 0.5375(3) 0.0922(3) 0.0256(6) Uani 1 1 d . . . . .
H11A H -0.048298 0.608257 0.101057 0.031 Uiso 1 1 calc R . . . .
H11B H -0.013045 0.469814 0.139868 0.031 Uiso 1 1 calc R . . . .
C12 C -0.0475(3) 0.5013(3) -0.0443(2) 0.0253(6) Uani 1 1 d . . . . .
H12A H -0.004521 0.424821 -0.052492 0.030 Uiso 1 1 calc R . . . .
H12B H -0.144257 0.487197 -0.075703 0.030 Uiso 1 1 calc R . . . .
C13 C -0.0178(3) 0.5999(3) -0.1211(2) 0.0227(6) Uani 1 1 d . . . . .
C14 C 0.1321(3) 0.6292(3) -0.0637(3) 0.0225(6) Uani 1 1 d . . . . .
H14 H 0.179396 0.551779 -0.063783 0.027 Uiso 1 1 calc R . . . .
C15 C 0.1536(3) 0.7117(3) -0.1584(3) 0.0265(6) Uani 1 1 d . . . . .
H15A H 0.246295 0.706969 -0.152263 0.032 Uiso 1 1 calc R . . . .
H15B H 0.132548 0.796836 -0.147078 0.032 Uiso 1 1 calc R . . . .
C16 C 0.0566(3) 0.6615(3) -0.2835(3) 0.0309(7) Uani 1 1 d . . . . .
H16A H 0.001902 0.727778 -0.334807 0.037 Uiso 1 1 calc R . . . .
H16B H 0.106109 0.622841 -0.328520 0.037 Uiso 1 1 calc R . . . .
C17 C -0.0322(3) 0.5674(3) -0.2547(2) 0.0249(6) Uani 1 1 d . . . . .
C18 C -0.1068(3) 0.7107(3) -0.1295(3) 0.0300(7) Uani 1 1 d . . . . .
H18A H -0.199947 0.686031 -0.165681 0.045 Uiso 1 1 calc GR . . . .
H18B H -0.090443 0.772847 -0.181337 0.045 Uiso 1 1 calc GR . . . .
H18C H -0.086444 0.743446 -0.046940 0.045 Uiso 1 1 calc GR . . . .
C20 C -0.1763(3) 0.5649(3) -0.3480(3) 0.0301(7) Uani 1 1 d . . . . .
C21 C -0.2591(3) 0.4557(3) -0.3507(3) 0.0323(7) Uani 1 1 d . . . . .
H21A H -0.339630 0.481108 -0.339726 0.048 Uiso 1 1 calc GR . . . .
H21B H -0.208449 0.400314 -0.284223 0.048 Uiso 1 1 calc GR . . . .
H21C H -0.283347 0.414419 -0.430060 0.048 Uiso 1 1 calc GR . . . .
C22 C 0.5467(3) 0.7227(3) 0.2898(3) 0.0326(7) Uani 1 1 d . . . . .
H22A H 0.563220 0.789067 0.348997 0.049 Uiso 1 1 calc GR . . . .
H22B H 0.568947 0.748977 0.220613 0.049 Uiso 1 1 calc GR . . . .
H22C H 0.601634 0.652893 0.330071 0.049 Uiso 1 1 calc GR . . . .
C23 C 0.0275(3) 0.3961(3) -0.3490(3) 0.0297(7) Uani 1 1 d . . . . .
C24 C 0.0981(3) 0.2777(3) -0.3264(3) 0.0362(7) Uani 1 1 d . . . . .
H24A H 0.193704 0.291723 -0.297189 0.054 Uiso 1 1 calc GR . . . .
H24B H 0.068664 0.231080 -0.403129 0.054 Uiso 1 1 calc GR . . . .
H24C H 0.078238 0.232262 -0.264114 0.054 Uiso 1 1 calc GR . . . .
O5 O 0.3403(2) 0.4818(2) -0.20063(19) 0.0354(5) Uani 1 1 d D . . . .
H5 H 0.381(4) 0.521(4) -0.244(3) 0.065(13) Uiso 1 1 d D . . . .
O6 O 0.8168(2) 0.4752(2) 0.3142(2) 0.0461(6) Uani 1 1 d D . . . .
H6 H 0.868(4) 0.454(4) 0.390(2) 0.064(12) Uiso 1 1 d D . . . .
O7 O 0.6830(3) 0.3469(2) 0.3567(2) 0.0486(7) Uani 1 1 d . . . . .
C25 C 0.4309(3) 0.4690(3) -0.0841(3) 0.0291(7) Uani 1 1 d . . . . .
C26 C 0.3987(3) 0.3932(3) -0.0049(3) 0.0338(7) Uani 1 1 d . . . . .
H26 H 0.315555 0.352945 -0.033221 0.041 Uiso 1 1 calc R . . . .
C27 C 0.4877(3) 0.3768(3) 0.1144(3) 0.0319(7) Uani 1 1 d . . . . .
H27 H 0.465483 0.324877 0.167872 0.038 Uiso 1 1 calc R . . . .
C28 C 0.6097(3) 0.4355(3) 0.1573(3) 0.0298(7) Uani 1 1 d . . . . .
C29 C 0.6404(3) 0.5105(3) 0.0779(3) 0.0332(7) Uani 1 1 d . . . . .
H29 H 0.723195 0.551318 0.106229 0.040 Uiso 1 1 calc R . . . .
C30 C 0.5518(3) 0.5268(3) -0.0425(3) 0.0349(7) Uani 1 1 d . . . . .
H30 H 0.574470 0.577804 -0.096343 0.042 Uiso 1 1 calc R . . . .
C31 C 0.7030(3) 0.4136(3) 0.2846(3) 0.0349(7) Uani 1 1 d . . . . .


_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 C3 1.235(3) . ?
O2 C20 1.212(4) . ?
O3 C17 1.474(3) . ?
O3 C23 1.344(3) . ?
O4 C23 1.207(4) . ?
C1 C2 1.529(4) . ?
C1 C10 1.520(4) . ?
C2 C3 1.489(4) . ?
C3 C4 1.455(4) . ?
C4 C5 1.347(4) . ?
C5 C6 1.471(4) . ?
C5 C10 1.520(4) . ?
C6 C7 1.340(4) . ?
C6 C22 1.509(4) . ?
C7 C8 1.502(4) . ?
C8 C9 1.535(4) . ?
C8 C14 1.523(4) . ?
C9 C10 1.539(4) . ?
C9 C11 1.529(4) . ?
C11 C12 1.538(4) . ?
C12 C13 1.529(4) . ?
C13 C14 1.548(4) . ?
C13 C17 1.562(4) . ?
C13 C18 1.543(4) . ?
C14 C15 1.527(4) . ?
C15 C16 1.548(4) . ?
C16 C17 1.547(4) . ?
C17 C20 1.536(4) . ?
C20 C21 1.501(4) . ?
C23 C24 1.489(5) . ?
O5 C25 1.355(3) . ?
O6 C31 1.343(4) . ?
O7 C31 1.207(4) . ?
C25 C26 1.397(4) . ?
C25 C30 1.378(4) . ?
C26 C27 1.378(4) . ?
C27 C28 1.393(4) . ?
C28 C29 1.385(4) . ?
C28 C31 1.472(4) . ?
C29 C30 1.387(4) . ?

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
C23 O3 C17 117.4(2) . . ?
C10 C1 C2 110.6(3) . . ?
C3 C2 C1 112.1(2) . . ?
O1 C3 C2 121.1(3) . . ?
O1 C3 C4 121.2(3) . . ?
C4 C3 C2 117.7(3) . . ?
C5 C4 C3 122.9(3) . . ?
C4 C5 C6 120.8(2) . . ?
C4 C5 C10 121.1(2) . . ?
C6 C5 C10 118.1(2) . . ?
C5 C6 C22 118.9(2) . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 C22 120.7(3) . . ?
C6 C7 C8 124.2(3) . . ?
C7 C8 C9 110.3(2) . . ?
C7 C8 C14 113.2(2) . . ?
C14 C8 C9 108.9(2) . . ?
C8 C9 C10 109.6(2) . . ?
C11 C9 C8 110.3(2) . . ?
C11 C9 C10 113.6(2) . . ?
C1 C10 C5 110.5(2) . . ?
C1 C10 C9 113.5(2) . . ?
C5 C10 C9 111.6(2) . . ?
C9 C11 C12 112.7(2) . . ?
C13 C12 C11 111.2(2) . . ?
C12 C13 C14 108.8(2) . . ?
C12 C13 C17 118.1(2) . . ?
C12 C13 C18 109.2(2) . . ?
C14 C13 C17 99.5(2) . . ?
C18 C13 C14 113.5(2) . . ?
C18 C13 C17 107.6(2) . . ?
C8 C14 C13 113.1(2) . . ?
C8 C14 C15 119.5(2) . . ?
C15 C14 C13 104.0(2) . . ?
C14 C15 C16 103.8(2) . . ?
C17 C16 C15 106.9(2) . . ?
O3 C17 C13 105.2(2) . . ?
O3 C17 C16 110.1(2) . . ?
O3 C17 C20 109.2(2) . . ?
C16 C17 C13 103.8(2) . . ?
C20 C17 C13 113.6(2) . . ?
C20 C17 C16 114.5(2) . . ?
O2 C20 C17 119.9(3) . . ?
O2 C20 C21 121.6(3) . . ?
C21 C20 C17 118.4(3) . . ?
O3 C23 C24 112.5(3) . . ?
O4 C23 O3 122.4(3) . . ?
O4 C23 C24 125.1(3) . . ?
O5 C25 C26 117.7(3) . . ?
O5 C25 C30 122.6(3) . . ?
C30 C25 C26 119.7(3) . . ?
C27 C26 C25 119.9(3) . . ?
C26 C27 C28 120.7(3) . . ?
C27 C28 C31 119.0(3) . . ?
C29 C28 C27 118.8(3) . . ?
C29 C28 C31 122.2(3) . . ?
C28 C29 C30 120.8(3) . . ?
C25 C30 C29 120.0(3) . . ?
O6 C31 C28 113.0(3) . . ?
O7 C31 O6 121.9(3) . . ?
O7 C31 C28 125.1(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.7(12)
2 -0.7(12)

####################################################################### 
# 
# 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_mo_20211126_0m
_database_code_depnum_ccdc_archive 'CCDC 2144828'
loop_
_audit_author_name
_audit_author_address
'Xiaofeng Chen'
;National Research Institute for Family Planning
China
;
_audit_update_record             
;
2022-07-28 deposited with the CCDC.	2022-08-12 downloaded from the CCDC.
;
_audit_creation_date             2022-07-28
_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         'C23 H30 O4, C7 H6 O4'
_chemical_formula_sum            'C30 H36 O8'
_chemical_formula_weight         524.59
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.8459(7)
_cell_length_b                   11.2095(7)
_cell_length_c                   11.9727(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.141(2)
_cell_angle_gamma                90
_cell_volume                     1328.30(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5793
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.363
_cell_measurement_theta_min      2.604
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1758 before and 0.0558 after correction. The Ratio of minimum to maximum transmission is 0.8766. 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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0472
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14222
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.058
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.856
_reflns_Friedel_fraction_max     0.822
_reflns_number_gt                4195
_reflns_number_total             4933
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_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         0.263
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.7(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     360
_refine_ls_number_reflns         4933
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.067
_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)+(0.0385P)²+0.2467P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0959
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.3(13)
 0.7(13)
2. 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
3. Restrained distances
 O7-H7A = O5-H5 = O8-H8A
 0.84 with sigma of 0.02
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B),
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C27(H27), C29(H29), C30(H30)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4479(2) 0.6103(3) 1.62485(19) 0.0473(6) Uani 1 1 d . . . . .
O2 O -0.2421(2) 0.6369(2) 0.5580(2) 0.0467(6) Uani 1 1 d . . . . .
O3 O 0.01105(19) 0.43663(19) 0.73408(16) 0.0276(5) Uani 1 1 d . . . . .
O4 O -0.0533(2) 0.4244(2) 0.53120(19) 0.0483(7) Uani 1 1 d . . . . .
C1 C 0.1730(3) 0.5146(3) 1.3409(3) 0.0376(8) Uani 1 1 d . . . . .
H1A H 0.075739 0.496288 1.313903 0.045 Uiso 1 1 calc R . . . .
H1B H 0.219808 0.440062 1.336483 0.045 Uiso 1 1 calc R . . . .
C2 C 0.2301(3) 0.5593(4) 1.4729(3) 0.0422(9) Uani 1 1 d . . . . .
H2A H 0.172517 0.624936 1.479870 0.051 Uiso 1 1 calc R . . . .
H2B H 0.227313 0.493755 1.527277 0.051 Uiso 1 1 calc R . . . .
C3 C 0.3716(3) 0.6028(3) 1.5144(3) 0.0344(7) Uani 1 1 d . . . . .
C4 C 0.4185(3) 0.6407(3) 1.4233(3) 0.0320(7) Uani 1 1 d . . . . .
H4 H 0.510457 0.663402 1.449657 0.038 Uiso 1 1 calc R . . . .
C5 C 0.3383(3) 0.6455(3) 1.3026(3) 0.0260(6) Uani 1 1 d . . . . .
C6 C 0.3906(3) 0.6914(3) 1.2160(3) 0.0280(6) Uani 1 1 d . . . . .
C7 C 0.3076(3) 0.7038(3) 1.0981(3) 0.0285(7) Uani 1 1 d . . . . .
H7 H 0.343246 0.738342 1.045089 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1623(3) 0.6669(3) 1.0437(2) 0.0245(6) Uani 1 1 d . . . . .
H8 H 0.106343 0.737517 1.044363 0.029 Uiso 1 1 calc R . . . .
C9 C 0.1378(3) 0.5679(3) 1.1208(2) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.192039 0.496964 1.117358 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1908(3) 0.6080(3) 1.2549(2) 0.0274(7) Uani 1 1 d . . . . .
H10 H 0.137691 0.679998 1.257702 0.033 Uiso 1 1 calc R . . . .
C11 C -0.0117(3) 0.5306(3) 1.0655(2) 0.0277(7) Uani 1 1 d . . . . .
H11A H -0.067346 0.598264 1.071543 0.033 Uiso 1 1 calc R . . . .
H11B H -0.024196 0.463537 1.113674 0.033 Uiso 1 1 calc R . . . .
C12 C -0.0613(3) 0.4924(3) 0.9305(2) 0.0267(6) Uani 1 1 d . . . . .
H12A H -0.013816 0.418603 0.925209 0.032 Uiso 1 1 calc R . . . .
H12B H -0.159238 0.474733 0.897479 0.032 Uiso 1 1 calc R . . . .
C13 C -0.0357(3) 0.5907(3) 0.8525(2) 0.0247(6) Uani 1 1 d . . . . .
C14 C 0.1153(3) 0.6237(3) 0.9118(2) 0.0234(6) Uani 1 1 d . . . . .
H14 H 0.166259 0.548494 0.915091 0.028 Uiso 1 1 calc R . . . .
C15 C 0.1353(3) 0.7037(3) 0.8173(2) 0.0288(7) Uani 1 1 d . . . . .
H15A H 0.230455 0.702113 0.827054 0.035 Uiso 1 1 calc R . . . .
H15B H 0.109346 0.787086 0.824412 0.035 Uiso 1 1 calc R . . . .
C16 C 0.0403(3) 0.6483(3) 0.6936(3) 0.0325(7) Uani 1 1 d . . . . .
H16A H -0.016131 0.710972 0.637841 0.039 Uiso 1 1 calc R . . . .
H16B H 0.093667 0.608562 0.654158 0.039 Uiso 1 1 calc R . . . .
C17 C -0.0495(3) 0.5567(3) 0.7213(2) 0.0269(6) Uani 1 1 d . . . . .
C18 C -0.1290(3) 0.6979(3) 0.8406(3) 0.0333(7) Uani 1 1 d . . . . .
H18A H -0.107341 0.732343 0.921743 0.050 Uiso 1 1 calc GR . . . .
H18B H -0.223375 0.671388 0.805210 0.050 Uiso 1 1 calc GR . . . .
H18C H -0.115782 0.758330 0.787369 0.050 Uiso 1 1 calc GR . . . .
C20 C -0.1964(3) 0.5533(3) 0.6259(3) 0.0328(7) Uani 1 1 d . . . . .
C21 C -0.2835(3) 0.4493(3) 0.6275(3) 0.0392(8) Uani 1 1 d . . . . .
H21A H -0.333767 0.469748 0.676745 0.059 Uiso 1 1 calc GR . . . .
H21B H -0.226325 0.379641 0.663067 0.059 Uiso 1 1 calc GR . . . .
H21C H -0.347239 0.430894 0.543617 0.059 Uiso 1 1 calc GR . . . .
C22 C 0.5373(3) 0.7277(3) 1.2631(3) 0.0370(8) Uani 1 1 d . . . . .
H22A H 0.552854 0.797580 1.316329 0.055 Uiso 1 1 calc GR . . . .
H22B H 0.559854 0.747342 1.193940 0.055 Uiso 1 1 calc GR . . . .
H22C H 0.594412 0.661622 1.309745 0.055 Uiso 1 1 calc GR . . . .
C23 C 0.0095(3) 0.3842(3) 0.6331(3) 0.0321(7) Uani 1 1 d . . . . .
C24 C 0.0921(3) 0.2737(3) 0.6604(3) 0.0393(8) Uani 1 1 d . . . . .
H24A H 0.185712 0.293905 0.676250 0.059 Uiso 1 1 calc GR . . . .
H24B H 0.055590 0.219421 0.590187 0.059 Uiso 1 1 calc GR . . . .
H24C H 0.089538 0.234698 0.732666 0.059 Uiso 1 1 calc GR . . . .
H7A H 0.488(5) 0.566(5) -0.226(3) 0.11(2) Uiso 1 1 d D . . . .
O5 O 0.3055(2) 0.3406(3) -0.0049(3) 0.0513(7) Uani 1 1 d D . . . .
H5 H 0.295(5) 0.368(5) -0.079(3) 0.093(18) Uiso 1 1 d D . . . .
O6 O 0.3283(2) 0.4649(2) -0.1807(2) 0.0403(6) Uani 1 1 d . . . . .
O7 O 0.5262(2) 0.5493(3) -0.1476(2) 0.0487(7) Uani 1 1 d D . . . .
O8 O 0.8218(3) 0.4947(3) 0.2859(2) 0.0484(7) Uani 1 1 d D . . . .
H8A H 0.842(5) 0.470(4) 0.358(3) 0.081(16) Uiso 1 1 d D . . . .
C25 C 0.4442(3) 0.4886(3) -0.1101(3) 0.0328(7) Uani 1 1 d . . . . .
C26 C 0.5055(3) 0.4533(3) 0.0187(3) 0.0337(7) Uani 1 1 d . . . . .
C27 C 0.6367(3) 0.4908(3) 0.0954(3) 0.0339(7) Uani 1 1 d . . . . .
H27 H 0.686281 0.539811 0.063564 0.041 Uiso 1 1 calc R . . . .
C28 C 0.6936(4) 0.4568(3) 0.2163(3) 0.0375(8) Uani 1 1 d . . . . .
C29 C 0.6200(4) 0.3853(3) 0.2627(3) 0.0420(8) Uani 1 1 d . . . . .
H29 H 0.659382 0.362110 0.346326 0.050 Uiso 1 1 calc R . . . .
C30 C 0.4907(4) 0.3478(3) 0.1887(3) 0.0441(9) Uani 1 1 d . . . . .
H30 H 0.441410 0.299327 0.221181 0.053 Uiso 1 1 calc R . . . .
C31 C 0.4331(3) 0.3819(3) 0.0657(3) 0.0375(8) Uani 1 1 d . . . . .


_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 C3 1.243(4) . ?
O2 C20 1.206(4) . ?
O3 C17 1.478(4) . ?
O3 C23 1.338(3) . ?
O4 C23 1.215(4) . ?
C1 C2 1.528(4) . ?
C1 C10 1.535(4) . ?
C2 C3 1.489(5) . ?
C3 C4 1.443(4) . ?
C4 C5 1.349(4) . ?
C5 C6 1.464(4) . ?
C5 C10 1.522(4) . ?
C6 C7 1.335(4) . ?
C6 C22 1.510(4) . ?
C7 C8 1.496(4) . ?
C8 C9 1.534(4) . ?
C8 C14 1.526(4) . ?
C9 C10 1.535(4) . ?
C9 C11 1.537(4) . ?
C11 C12 1.542(4) . ?
C12 C13 1.541(4) . ?
C13 C14 1.541(4) . ?
C13 C17 1.563(4) . ?
C13 C18 1.541(4) . ?
C14 C15 1.526(4) . ?
C15 C16 1.547(4) . ?
C16 C17 1.541(4) . ?
C17 C20 1.535(4) . ?
C20 C21 1.505(5) . ?
C23 C24 1.485(5) . ?
O5 C31 1.373(4) . ?
O6 C25 1.223(4) . ?
O7 C25 1.335(4) . ?
O8 C28 1.364(4) . ?
C25 C26 1.462(4) . ?
C26 C27 1.406(5) . ?
C26 C31 1.391(5) . ?
C27 C28 1.376(4) . ?
C28 C29 1.396(5) . ?
C29 C30 1.383(5) . ?
C30 C31 1.398(5) . ?

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
C23 O3 C17 117.7(2) . . ?
C2 C1 C10 111.2(3) . . ?
C3 C2 C1 112.3(3) . . ?
O1 C3 C2 121.6(3) . . ?
O1 C3 C4 119.8(3) . . ?
C4 C3 C2 118.6(3) . . ?
C5 C4 C3 123.4(3) . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 C10 120.6(3) . . ?
C6 C5 C10 118.9(2) . . ?
C5 C6 C22 118.9(2) . . ?
C7 C6 C5 119.8(3) . . ?
C7 C6 C22 121.3(3) . . ?
C6 C7 C8 124.5(3) . . ?
C7 C8 C9 110.4(2) . . ?
C7 C8 C14 112.6(2) . . ?
C14 C8 C9 109.1(2) . . ?
C8 C9 C10 109.6(2) . . ?
C8 C9 C11 110.5(2) . . ?
C10 C9 C11 114.0(2) . . ?
C1 C10 C9 113.9(2) . . ?
C5 C10 C1 109.8(2) . . ?
C5 C10 C9 111.1(2) . . ?
C9 C11 C12 112.4(2) . . ?
C13 C12 C11 111.4(2) . . ?
C12 C13 C17 117.9(2) . . ?
C14 C13 C12 108.3(2) . . ?
C14 C13 C17 99.7(2) . . ?
C14 C13 C18 112.9(3) . . ?
C18 C13 C12 109.8(2) . . ?
C18 C13 C17 108.0(2) . . ?
C8 C14 C13 113.3(2) . . ?
C8 C14 C15 119.5(2) . . ?
C15 C14 C13 104.3(2) . . ?
C14 C15 C16 103.5(2) . . ?
C17 C16 C15 107.1(2) . . ?
O3 C17 C13 105.2(2) . . ?
O3 C17 C16 109.6(2) . . ?
O3 C17 C20 109.7(2) . . ?
C16 C17 C13 104.1(2) . . ?
C20 C17 C13 113.4(2) . . ?
C20 C17 C16 114.3(2) . . ?
O2 C20 C17 119.8(3) . . ?
O2 C20 C21 121.5(3) . . ?
C21 C20 C17 118.4(3) . . ?
O3 C23 C24 112.6(3) . . ?
O4 C23 O3 122.7(3) . . ?
O4 C23 C24 124.7(3) . . ?
O6 C25 O7 121.1(3) . . ?
O6 C25 C26 124.4(3) . . ?
O7 C25 C26 114.5(3) . . ?
C27 C26 C25 120.7(3) . . ?
C31 C26 C25 119.6(3) . . ?
C31 C26 C27 119.8(3) . . ?
C28 C27 C26 120.2(3) . . ?
O8 C28 C27 117.5(3) . . ?
O8 C28 C29 122.8(3) . . ?
C27 C28 C29 119.7(3) . . ?
C30 C29 C28 120.9(3) . . ?
C29 C30 C31 119.4(3) . . ?
O5 C31 C26 122.6(3) . . ?
O5 C31 C30 117.4(3) . . ?
C26 C31 C30 120.0(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5 O6 0.90(2) 1.77(3) 2.618(4) 155(5) . yes


_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.3(13)
2 0.7(13)

