# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_shi_4023_cota
_database_code_depnum_ccdc_archive 'CCDC 1883073'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-12-04
_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         'C17 H22 O4'
_chemical_formula_sum            'C17 H22 O4'
_chemical_formula_weight         290.34
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20O4Cl1
_chemical_oxdiff_usercomment     TCV-14/092018
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      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.6481(17)
_cell_length_b                   30.186(4)
_cell_length_c                   6.7702(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1563.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.7040
_cell_measurement_theta_min      2.6690
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90701
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0742
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            4747
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         2.699
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  22.00   1.00   15.00    --   22.46  77.00 -60.00   26
  2  ω     -9.00  94.00   1.00   15.00    --   22.46  77.00-180.00  103
  3  ω     13.00  78.00   1.00   15.00    --   22.46  77.00  60.00   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0185801000
_diffrn_orient_matrix_UB_12      0.0169949000
_diffrn_orient_matrix_UB_13      0.0227878000
_diffrn_orient_matrix_UB_21      -0.0450829000
_diffrn_orient_matrix_UB_22      -0.0833979000
_diffrn_orient_matrix_UB_23      0.0021499000
_diffrn_orient_matrix_UB_31      0.0930202000
_diffrn_orient_matrix_UB_32      -0.0371568000
_diffrn_orient_matrix_UB_33      0.0056225000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.681
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                1773
_reflns_number_total             2747
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.205
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 404 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2747
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0804
_refine_ls_restrained_S_all      1.102
_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)+(0.0566P)²+0.1203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1489
_refine_ls_wR_factor_ref         0.1731
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C13(H13A,H13B),
 C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.7648(8) 0.48040(14) 0.2153(7) 0.0947(18) Uani 1 1 d . . . . .
O2 O 0.4743(6) 0.70927(13) 0.8451(6) 0.0680(13) Uani 1 1 d . . . . .
H2 H 0.432419 0.714397 0.954208 0.102 Uiso 1 1 calc GR . . . .
O3 O 0.8285(6) 0.75373(11) 0.8021(5) 0.0592(12) Uani 1 1 d . . . . .
O4 O 0.6836(7) 0.80697(14) 0.6432(7) 0.0820(15) Uani 1 1 d . . . . .
C1 C 0.7780(9) 0.4544(2) 0.0546(9) 0.0651(18) Uani 1 1 d . . . . .
C2 C 0.7988(9) 0.4099(2) 0.0893(10) 0.0714(19) Uani 1 1 d . . . . .
H2A H 0.801647 0.399653 0.218745 0.086 Uiso 1 1 calc R . . . .
C3 C 0.8153(9) 0.3808(2) -0.0608(12) 0.077(2) Uani 1 1 d . . . . .
H3 H 0.827540 0.350742 -0.034802 0.092 Uiso 1 1 calc R . . . .
C4 C 0.8140(10) 0.3958(2) -0.2512(12) 0.078(2) Uani 1 1 d . . . . .
H4 H 0.827077 0.375894 -0.354912 0.093 Uiso 1 1 calc R . . . .
C5 C 0.7932(9) 0.4406(2) -0.2903(10) 0.074(2) Uani 1 1 d . . . . .
H5 H 0.790172 0.450344 -0.420539 0.089 Uiso 1 1 calc R . . . .
C6 C 0.7769(9) 0.47073(19) -0.1386(9) 0.0689(19) Uani 1 1 d . . . . .
H6 H 0.765666 0.500875 -0.163846 0.083 Uiso 1 1 calc R . . . .
C7 C 0.7385(10) 0.52649(19) 0.1918(9) 0.074(2) Uani 1 1 d . . . . .
H7A H 0.630530 0.532204 0.121016 0.089 Uiso 1 1 calc R . . . .
H7B H 0.834581 0.539612 0.118809 0.089 Uiso 1 1 calc R . . . .
C8 C 0.7295(11) 0.5456(2) 0.4008(10) 0.085(2) Uani 1 1 d . . . . .
H8A H 0.635525 0.530967 0.471617 0.102 Uiso 1 1 calc R . . . .
H8B H 0.837831 0.538733 0.468662 0.102 Uiso 1 1 calc R . . . .
C9 C 0.7007(10) 0.59381(19) 0.4101(9) 0.073(2) Uani 1 1 d . . . . .
H9A H 0.594235 0.601197 0.339580 0.088 Uiso 1 1 calc R . . . .
H9B H 0.797096 0.608898 0.345643 0.088 Uiso 1 1 calc R . . . .
C10 C 0.6859(8) 0.61019(17) 0.6277(8) 0.0585(17) Uani 1 1 d . . . . .
H10A H 0.601238 0.592000 0.696893 0.070 Uiso 1 1 calc R . . . .
H10B H 0.798098 0.606405 0.692405 0.070 Uiso 1 1 calc R . . . .
C11 C 0.6309(8) 0.65870(17) 0.6430(8) 0.0481(15) Uani 1 1 d . . . . .
H11 H 0.529532 0.664021 0.557791 0.058 Uiso 1 1 calc R . . . .
C12 C 0.5854(8) 0.67116(18) 0.8568(8) 0.0504(15) Uani 1 1 d . . . . .
H12 H 0.527988 0.646641 0.926060 0.060 Uiso 1 1 calc R . . . .
C13 C 0.7621(10) 0.68213(18) 0.9479(8) 0.0619(17) Uani 1 1 d . . . . .
H13A H 0.748156 0.700749 1.063623 0.074 Uiso 1 1 calc R . . . .
H13B H 0.823512 0.655318 0.985771 0.074 Uiso 1 1 calc R . . . .
C14 C 0.8597(8) 0.70634(18) 0.7876(8) 0.0522(16) Uani 1 1 d . . . . .
H14 H 0.985076 0.699721 0.792978 0.063 Uiso 1 1 calc R . . . .
C15 C 0.7793(8) 0.69110(17) 0.5878(7) 0.0471(14) Uani 1 1 d . . . . .
H15 H 0.867377 0.676400 0.505644 0.057 Uiso 1 1 calc R . . . .
C16 C 0.7198(8) 0.73474(17) 0.4933(8) 0.0558(16) Uani 1 1 d . . . . .
H16A H 0.793049 0.741899 0.380813 0.067 Uiso 1 1 calc R . . . .
H16B H 0.599654 0.732353 0.448595 0.067 Uiso 1 1 calc R . . . .
C17 C 0.7353(8) 0.76943(19) 0.6470(8) 0.0541(15) 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 C1 1.345(7) . ?
O1 C7 1.415(6) . ?
O2 C12 1.432(6) . ?
O3 C14 1.454(6) . ?
O3 C17 1.354(7) . ?
O4 C17 1.201(6) . ?
C1 C2 1.372(8) . ?
C1 C6 1.397(8) . ?
C2 C3 1.349(8) . ?
C3 C4 1.366(10) . ?
C4 C5 1.385(8) . ?
C5 C6 1.379(8) . ?
C7 C8 1.530(8) . ?
C8 C9 1.473(7) . ?
C9 C10 1.558(8) . ?
C10 C11 1.527(7) . ?
C11 C12 1.535(7) . ?
C11 C15 1.544(7) . ?
C12 C13 1.523(9) . ?
C13 C14 1.506(8) . ?
C14 C15 1.555(7) . ?
C15 C16 1.534(7) . ?
C16 C17 1.481(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C7 119.5(5) . . ?
C17 O3 C14 112.2(4) . . ?
O1 C1 C2 116.2(6) . . ?
O1 C1 C6 123.4(6) . . ?
C2 C1 C6 120.4(6) . . ?
C3 C2 C1 121.3(7) . . ?
C2 C3 C4 119.6(7) . . ?
C3 C4 C5 120.3(7) . . ?
C6 C5 C4 120.8(6) . . ?
C5 C6 C1 117.7(6) . . ?
O1 C7 C8 105.8(5) . . ?
C9 C8 C7 114.7(6) . . ?
C8 C9 C10 111.4(5) . . ?
C11 C10 C9 112.9(5) . . ?
C10 C11 C12 111.2(5) . . ?
C10 C11 C15 112.9(5) . . ?
C12 C11 C15 103.9(4) . . ?
O2 C12 C11 106.2(5) . . ?
O2 C12 C13 112.0(5) . . ?
C13 C12 C11 103.5(5) . . ?
C14 C13 C12 104.7(5) . . ?
O3 C14 C13 110.3(5) . . ?
O3 C14 C15 106.5(4) . . ?
C13 C14 C15 106.7(4) . . ?
C11 C15 C14 105.5(4) . . ?
C16 C15 C11 115.3(5) . . ?
C16 C15 C14 103.1(4) . . ?
C17 C16 C15 106.9(4) . . ?
O3 C17 C16 109.8(5) . . ?
O4 C17 O3 121.3(5) . . ?
O4 C17 C16 128.8(6) . . ?

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
O2 H2 O3 0.82 2.07 2.863(5) 163.0 4_467 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.3(6) . . . . ?
O1 C1 C6 C5 179.4(7) . . . . ?
O1 C7 C8 C9 -179.5(6) . . . . ?
O2 C12 C13 C14 -75.1(5) . . . . ?
O3 C14 C15 C11 -116.4(5) . . . . ?
O3 C14 C15 C16 4.9(6) . . . . ?
C1 O1 C7 C8 179.9(7) . . . . ?
C1 C2 C3 C4 1.0(12) . . . . ?
C2 C1 C6 C5 1.5(11) . . . . ?
C2 C3 C4 C5 -1.0(12) . . . . ?
C3 C4 C5 C6 1.2(11) . . . . ?
C4 C5 C6 C1 -1.5(10) . . . . ?
C6 C1 C2 C3 -1.3(12) . . . . ?
C7 O1 C1 C2 -178.4(7) . . . . ?
C7 O1 C1 C6 3.7(10) . . . . ?
C7 C8 C9 C10 177.8(6) . . . . ?
C8 C9 C10 C11 -172.0(6) . . . . ?
C9 C10 C11 C12 169.6(5) . . . . ?
C9 C10 C11 C15 -74.1(7) . . . . ?
C10 C11 C12 O2 -157.8(5) . . . . ?
C10 C11 C12 C13 84.1(6) . . . . ?
C10 C11 C15 C14 -98.4(5) . . . . ?
C10 C11 C15 C16 148.6(5) . . . . ?
C11 C12 C13 C14 38.9(6) . . . . ?
C11 C15 C16 C17 104.2(5) . . . . ?
C12 C11 C15 C14 22.1(6) . . . . ?
C12 C11 C15 C16 -90.9(5) . . . . ?
C12 C13 C14 O3 90.5(5) . . . . ?
C12 C13 C14 C15 -24.9(6) . . . . ?
C13 C14 C15 C11 1.5(6) . . . . ?
C13 C14 C15 C16 122.8(5) . . . . ?
C14 O3 C17 O4 173.1(6) . . . . ?
C14 O3 C17 C16 -9.6(7) . . . . ?
C14 C15 C16 C17 -10.2(6) . . . . ?
C15 C11 C12 O2 80.5(5) . . . . ?
C15 C11 C12 C13 -37.6(6) . . . . ?
C15 C16 C17 O3 12.5(7) . . . . ?
C15 C16 C17 O4 -170.4(7) . . . . ?
C17 O3 C14 C13 -112.8(5) . . . . ?
C17 O3 C14 C15 2.6(6) . . . . ?

_olex2_date_sample_data_collection 2018-11-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.114
_oxdiff_exptl_absorpt_empirical_full_min 0.875
####################################################################### 
# 
# 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_shi_3239_cota
_database_code_depnum_ccdc_archive 'CCDC 1878353'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2019-04-29 deposited with the CCDC.	2019-05-01 downloaded from the CCDC.
;
_audit_creation_date             2018-11-11
_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         'C19 H24 O4'
_chemical_formula_sum            'C19 H24 O4'
_chemical_formula_weight         316.38
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H15 O2'
_chemical_oxdiff_usercomment     'fara eticheta'
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                   7.4702(4)
_cell_length_b                   8.3687(4)
_cell_length_c                   13.8595(7)
_cell_angle_alpha                90
_cell_angle_beta                 103.173(5)
_cell_angle_gamma                90
_cell_volume                     843.64(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1663
_cell_measurement_temperature    160.00(10)
_cell_measurement_theta_max      24.5960
_cell_measurement_theta_min      2.8010
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.962
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         2.800
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      160.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -39.00  -4.00   1.00    3.00    --  -15.44  77.00  90.00   35
  2  ω      1.00  45.00   1.00    3.00    --  -15.44  77.00  60.00   44
  3  ω     -2.00  73.00   1.00    3.00    --   17.87  77.00  60.00   75
  4  ω      5.00  85.00   1.00    3.00    --   17.87  77.00 -60.00   80
  5  ω     11.00  44.00   1.00    3.00    --  -15.44  77.00-180.00   33
  6  ω    -40.00  47.00   1.00    3.00    --  -15.44  77.00 150.00   87
  7  ω      8.00  34.00   1.00    3.00    --   17.71  38.00-150.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0392983000
_diffrn_orient_matrix_UB_12      -0.0144269000
_diffrn_orient_matrix_UB_13      0.0508367000
_diffrn_orient_matrix_UB_21      0.0881434000
_diffrn_orient_matrix_UB_22      0.0194400000
_diffrn_orient_matrix_UB_23      -0.0077102000
_diffrn_orient_matrix_UB_31      -0.0140683000
_diffrn_orient_matrix_UB_32      0.0812253000
_diffrn_orient_matrix_UB_33      0.0108460000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.859
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2451
_reflns_number_total             2976
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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         0.134
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 883 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2976
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.039
_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)+(0.0391P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0852
_refine_ls_wR_factor_ref         0.0950
_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:
 C3(H3), C4(H4), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C9(H9A,H9B), C12(H12A,H12B), C13(H13A,
 H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.9506(3) -0.8573(3) -0.08129(18) 0.0526(8) Uani 1 1 d . . . . .
O2 O -0.6708(3) -0.7513(3) -0.04800(16) 0.0390(6) Uani 1 1 d . . . . .
O3 O -0.3841(3) -0.4482(2) -0.24105(16) 0.0276(5) Uani 1 1 d . . . . .
O4 O -0.3936(3) -0.1687(3) -0.25496(16) 0.0329(6) Uani 1 1 d . . . . .
C1 C -0.8557(5) -0.7394(5) -0.0766(2) 0.0392(9) Uani 1 1 d . . . . .
C2 C -0.9141(4) -0.5701(4) -0.0982(2) 0.0368(9) Uani 1 1 d . . . . .
H2A H -0.973447 -0.528796 -0.047958 0.044 Uiso 1 1 calc R . . . .
H2B H -0.998664 -0.561380 -0.162423 0.044 Uiso 1 1 calc R . . . .
C3 C -0.7376(4) -0.4805(4) -0.0971(2) 0.0332(8) Uani 1 1 d . . . . .
H3 H -0.735548 -0.378091 -0.062560 0.040 Uiso 1 1 calc R . . . .
C4 C -0.5862(4) -0.5934(4) -0.0396(3) 0.0356(8) Uani 1 1 d . . . . .
H4 H -0.545781 -0.560873 0.029845 0.043 Uiso 1 1 calc R . . . .
C5 C -0.4261(4) -0.5910(4) -0.0919(2) 0.0388(9) Uani 1 1 d . . . . .
H5A H -0.309473 -0.574760 -0.045024 0.047 Uiso 1 1 calc R . . . .
H5B H -0.420684 -0.689071 -0.128355 0.047 Uiso 1 1 calc R . . . .
C6 C -0.4751(4) -0.4490(4) -0.1613(2) 0.0281(7) Uani 1 1 d . . . . .
H6 H -0.443360 -0.350620 -0.122806 0.034 Uiso 1 1 calc R . . . .
C7 C -0.6825(4) -0.4588(4) -0.1955(2) 0.0266(7) Uani 1 1 d . . . . .
H7 H -0.714047 -0.556333 -0.234801 0.032 Uiso 1 1 calc R . . . .
C8 C -0.7521(4) -0.3168(4) -0.2604(2) 0.0327(8) Uani 1 1 d . . . . .
H8A H -0.732285 -0.219388 -0.221507 0.039 Uiso 1 1 calc R . . . .
H8B H -0.882892 -0.327900 -0.288425 0.039 Uiso 1 1 calc R . . . .
C9 C -0.6475(4) -0.3090(4) -0.3436(2) 0.0301(7) Uani 1 1 d . . . . .
H9A H -0.686469 -0.397302 -0.388806 0.036 Uiso 1 1 calc R . . . .
H9B H -0.679713 -0.210587 -0.380404 0.036 Uiso 1 1 calc R . . . .
C10 C -0.4397(4) -0.3160(4) -0.3060(2) 0.0268(7) Uani 1 1 d . . . . .
C11 C -0.2055(4) -0.1491(5) -0.2061(3) 0.0444(10) Uani 1 1 d . . . . .
H11A H -0.192721 -0.056916 -0.163848 0.067 Uiso 1 1 calc GR . . . .
H11B H -0.133226 -0.134932 -0.254521 0.067 Uiso 1 1 calc GR . . . .
H11C H -0.163836 -0.242224 -0.166962 0.067 Uiso 1 1 calc GR . . . .
C12 C -0.3387(4) -0.3408(4) -0.3883(2) 0.0295(8) Uani 1 1 d . . . . .
H12A H -0.380456 -0.440423 -0.421713 0.035 Uiso 1 1 calc R . . . .
H12B H -0.208670 -0.352216 -0.358581 0.035 Uiso 1 1 calc R . . . .
C13 C -0.3623(5) -0.2085(4) -0.4660(3) 0.0409(9) Uani 1 1 d . . . . .
H13A H -0.490620 -0.201338 -0.500238 0.049 Uiso 1 1 calc R . . . .
H13B H -0.326684 -0.106988 -0.433424 0.049 Uiso 1 1 calc R . . . .
C14 C -0.2472(4) -0.2401(4) -0.5399(2) 0.0299(8) Uani 1 1 d . . . . .
C15 C -0.3088(5) -0.3388(4) -0.6210(3) 0.0409(9) Uani 1 1 d . . . . .
H15 H -0.426107 -0.382638 -0.631847 0.049 Uiso 1 1 calc R . . . .
C16 C -0.1986(6) -0.3729(5) -0.6860(3) 0.0504(11) Uani 1 1 d . . . . .
H16 H -0.242284 -0.439050 -0.740159 0.060 Uiso 1 1 calc R . . . .
C17 C -0.0260(6) -0.3099(5) -0.6711(3) 0.0473(10) Uani 1 1 d . . . . .
H17 H 0.048417 -0.334017 -0.714565 0.057 Uiso 1 1 calc R . . . .
C18 C 0.0372(5) -0.2109(4) -0.5918(3) 0.0429(10) Uani 1 1 d . . . . .
H18 H 0.154650 -0.167495 -0.581588 0.051 Uiso 1 1 calc R . . . .
C19 C -0.0730(4) -0.1755(4) -0.5271(2) 0.0354(8) Uani 1 1 d . . . . .
H19 H -0.029399 -0.107086 -0.474033 0.042 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 C1 1.208(4) . ?
O2 C1 1.352(4) . ?
O2 C4 1.457(4) . ?
O3 C6 1.424(4) . ?
O3 C10 1.427(4) . ?
O4 C10 1.424(4) . ?
O4 C11 1.423(4) . ?
C1 C2 1.492(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.514(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.547(5) . ?
C3 C7 1.523(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.533(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.520(4) . ?
C6 H6 0.9800 . ?
C6 C7 1.516(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.509(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.534(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.522(4) . ?
C10 C12 1.519(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.526(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.503(4) . ?
C14 C15 1.387(5) . ?
C14 C19 1.383(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.382(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.364(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.372(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.381(4) . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C4 110.6(3) . . ?
C6 O3 C10 111.8(2) . . ?
C11 O4 C10 115.9(2) . . ?
O1 C1 O2 120.3(4) . . ?
O1 C1 C2 128.6(3) . . ?
O2 C1 C2 111.2(3) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.7(3) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3 110.8 . . ?
C2 C3 C4 103.6(3) . . ?
C2 C3 C7 117.6(3) . . ?
C4 C3 H3 110.8 . . ?
C7 C3 H3 110.8 . . ?
C7 C3 C4 102.6(3) . . ?
O2 C4 C3 105.1(2) . . ?
O2 C4 H4 111.2 . . ?
O2 C4 C5 110.2(3) . . ?
C3 C4 H4 111.2 . . ?
C5 C4 C3 107.8(3) . . ?
C5 C4 H4 111.2 . . ?
C4 C5 H5A 111.4 . . ?
C4 C5 H5B 111.4 . . ?
H5A C5 H5B 109.2 . . ?
C6 C5 C4 102.0(3) . . ?
C6 C5 H5A 111.4 . . ?
C6 C5 H5B 111.4 . . ?
O3 C6 C5 114.0(2) . . ?
O3 C6 H6 108.6 . . ?
O3 C6 C7 113.1(2) . . ?
C5 C6 H6 108.6 . . ?
C7 C6 C5 103.8(2) . . ?
C7 C6 H6 108.6 . . ?
C3 C7 H7 108.6 . . ?
C6 C7 C3 101.0(2) . . ?
C6 C7 H7 108.6 . . ?
C8 C7 C3 120.1(3) . . ?
C8 C7 C6 109.5(2) . . ?
C8 C7 H7 108.6 . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
C7 C8 C9 108.4(3) . . ?
H8A C8 H8B 108.4 . . ?
C9 C8 H8A 110.0 . . ?
C9 C8 H8B 110.0 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.3(2) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
O3 C10 C9 111.9(2) . . ?
O3 C10 C12 104.2(2) . . ?
O4 C10 O3 110.8(2) . . ?
O4 C10 C9 104.4(2) . . ?
O4 C10 C12 112.7(2) . . ?
C12 C10 C9 113.0(3) . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 108.4 . . ?
C10 C12 H12B 108.4 . . ?
C10 C12 C13 115.7(3) . . ?
H12A C12 H12B 107.4 . . ?
C13 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C12 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C12 111.1(3) . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
C15 C14 C13 121.4(3) . . ?
C19 C14 C13 120.8(3) . . ?
C19 C14 C15 117.8(3) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.7(3) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.2(3) . . ?
C19 C18 H18 119.9 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 121.0(3) . . ?
C18 C19 H19 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -170.5(3) . . . . ?
O2 C1 C2 C3 10.0(4) . . . . ?
O2 C4 C5 C6 126.7(3) . . . . ?
O3 C6 C7 C3 172.6(3) . . . . ?
O3 C6 C7 C8 -59.8(3) . . . . ?
O3 C10 C12 C13 -175.8(3) . . . . ?
O4 C10 C12 C13 -55.6(4) . . . . ?
C1 O2 C4 C3 -16.7(3) . . . . ?
C1 O2 C4 C5 -132.6(3) . . . . ?
C1 C2 C3 C4 -19.1(3) . . . . ?
C1 C2 C3 C7 93.3(3) . . . . ?
C2 C3 C4 O2 21.8(3) . . . . ?
C2 C3 C4 C5 139.3(3) . . . . ?
C2 C3 C7 C6 -151.8(3) . . . . ?
C2 C3 C7 C8 87.8(4) . . . . ?
C3 C4 C5 C6 12.5(3) . . . . ?
C3 C7 C8 C9 169.6(3) . . . . ?
C4 O2 C1 O1 -175.2(3) . . . . ?
C4 O2 C1 C2 4.4(4) . . . . ?
C4 C3 C7 C6 -38.9(3) . . . . ?
C4 C3 C7 C8 -159.3(2) . . . . ?
C4 C5 C6 O3 -160.8(3) . . . . ?
C4 C5 C6 C7 -37.4(3) . . . . ?
C5 C6 C7 C3 48.6(3) . . . . ?
C5 C6 C7 C8 176.2(3) . . . . ?
C6 O3 C10 O4 61.9(3) . . . . ?
C6 O3 C10 C9 -54.2(3) . . . . ?
C6 O3 C10 C12 -176.7(2) . . . . ?
C6 C7 C8 C9 53.5(3) . . . . ?
C7 C3 C4 O2 -101.1(3) . . . . ?
C7 C3 C4 C5 16.5(3) . . . . ?
C7 C8 C9 C10 -51.2(3) . . . . ?
C8 C9 C10 O3 51.5(4) . . . . ?
C8 C9 C10 O4 -68.4(3) . . . . ?
C8 C9 C10 C12 168.8(3) . . . . ?
C9 C10 C12 C13 62.5(4) . . . . ?
C10 O3 C6 C5 177.8(2) . . . . ?
C10 O3 C6 C7 59.6(3) . . . . ?
C10 C12 C13 C14 176.3(3) . . . . ?
C11 O4 C10 O3 55.2(3) . . . . ?
C11 O4 C10 C9 175.9(2) . . . . ?
C11 O4 C10 C12 -61.1(3) . . . . ?
C12 C13 C14 C15 83.9(4) . . . . ?
C12 C13 C14 C19 -93.9(4) . . . . ?
C13 C14 C15 C16 -177.0(3) . . . . ?
C13 C14 C19 C18 176.5(3) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C14 C19 C18 -1.4(5) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C19 0.2(5) . . . . ?
C17 C18 C19 C14 0.9(5) . . . . ?
C19 C14 C15 C16 0.9(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.094
_oxdiff_exptl_absorpt_empirical_full_min 0.877
