# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_exp_477
_database_code_depnum_ccdc_archive 'CCDC 1521972'
_audit_update_record             
;
2016-12-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-12-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H16 O2'
_chemical_formula_sum            'C16 H16 O2'
_chemical_formula_weight         240.29
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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                   7.5822(4)
_cell_length_b                   8.8509(5)
_cell_length_c                   10.0505(6)
_cell_angle_alpha                93.807(5)
_cell_angle_beta                 110.400(5)
_cell_angle_gamma                92.911(5)
_cell_volume                     628.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2022
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.0830
_cell_measurement_theta_min      6.2380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3341
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.593
_diffrn_reflns_theta_min         6.247
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9836
_diffrn_measured_fraction_theta_max 0.9419
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   38.0000   30.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -69.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   77.0000 -120.0000 103

#__ type_ start__ end____ width___ exp.time_
  3 omega  -73.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9538   77.0000  120.0000 102

#__ type_ start__ end____ width___ exp.time_
  4 omega   62.00  167.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   15.0000   90.0000 105

#__ type_ start__ end____ width___ exp.time_
  5 omega  108.00  177.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  125.0000  -30.0000 69

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   30.0000  -30.0000 97

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  134.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -77.0000 -120.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   87.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -61.0000   60.0000 90

#__ type_ start__ end____ width___ exp.time_
 10 omega   48.00  119.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826 -125.0000   90.0000 71

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   85.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000  -60.0000 49

#__ type_ start__ end____ width___ exp.time_
 12 omega   42.00   93.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000 -180.0000 51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0004652000
_diffrn_orient_matrix_UB_12      -0.1608855000
_diffrn_orient_matrix_UB_13      -0.0684680000
_diffrn_orient_matrix_UB_21      0.0626633000
_diffrn_orient_matrix_UB_22      -0.0604112000
_diffrn_orient_matrix_UB_23      0.1483809000
_diffrn_orient_matrix_UB_31      -0.2082331000
_diffrn_orient_matrix_UB_32      -0.0329857000
_diffrn_orient_matrix_UB_33      -0.0160620000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1990
_reflns_number_total             2180
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.303
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.047
_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)+(0.0668P)²+0.2704P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1266
_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 Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C15(H15), C16(H16)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.7366(2) 0.17497(14) 0.59993(13) 0.0525(4) Uani 1 1 d . . . . .
O2 O 0.64415(15) 0.56841(12) 0.34613(11) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.7785(3) 0.8256(2) 0.4409(2) 0.0456(5) Uani 1 1 d . . . . .
H1A H 0.8609 0.8358 0.3875 0.068 Uiso 1 1 calc GR . . . .
H1B H 0.8330 0.8847 0.5312 0.068 Uiso 1 1 calc GR . . . .
H1C H 0.6584 0.8612 0.3887 0.068 Uiso 1 1 calc GR . . . .
C2 C 0.7525(2) 0.66380(18) 0.46439(18) 0.0328(4) Uani 1 1 d . . . . .
C3 C 0.8129(2) 0.58301(17) 0.57854(17) 0.0294(4) Uani 1 1 d . . . . .
C4 C 0.9373(2) 0.6359(2) 0.72863(18) 0.0375(4) Uani 1 1 d . . . . .
H4A H 0.8640 0.6870 0.7774 0.045 Uiso 1 1 calc R . . . .
H4B H 1.0377 0.7077 0.7275 0.045 Uiso 1 1 calc R . . . .
C5 C 1.0223(3) 0.5005(2) 0.80807(18) 0.0425(5) Uani 1 1 d . . . . .
H5A H 1.1196 0.4655 0.7741 0.051 Uiso 1 1 calc R . . . .
H5B H 1.0810 0.5325 0.9090 0.051 Uiso 1 1 calc R . . . .
C6 C 0.8738(3) 0.3706(2) 0.78702(18) 0.0414(4) Uani 1 1 d . . . . .
H6A H 0.7791 0.4051 0.8241 0.050 Uiso 1 1 calc R . . . .
H6B H 0.9327 0.2885 0.8412 0.050 Uiso 1 1 calc R . . . .
C7 C 0.7778(2) 0.31076(19) 0.63170(17) 0.0343(4) Uani 1 1 d . . . . .
C8 C 0.7393(2) 0.42788(17) 0.53094(16) 0.0280(4) Uani 1 1 d . . . . .
C9 C 0.6385(2) 0.42358(17) 0.38708(16) 0.0266(3) Uani 1 1 d . . . . .
C10 C 0.5320(2) 0.30985(17) 0.27060(15) 0.0256(3) Uani 1 1 d . . . . .
C11 C 0.4738(2) 0.16477(18) 0.29377(17) 0.0306(4) Uani 1 1 d . . . . .
H11 H 0.5079 0.1363 0.3863 0.037 Uiso 1 1 calc R . . . .
C12 C 0.3662(2) 0.06299(18) 0.18050(17) 0.0325(4) Uani 1 1 d . . . . .
H12 H 0.3277 -0.0324 0.1988 0.039 Uiso 1 1 calc R . . . .
C13 C 0.3139(2) 0.09922(18) 0.04031(17) 0.0309(4) Uani 1 1 d . . . . .
C14 C 0.1973(2) -0.0134(2) -0.08149(18) 0.0391(4) Uani 1 1 d . . . . .
H14A H 0.2766 -0.0554 -0.1286 0.059 Uiso 1 1 calc GR . . . .
H14B H 0.0995 0.0369 -0.1480 0.059 Uiso 1 1 calc GR . . . .
H14C H 0.1414 -0.0934 -0.0456 0.059 Uiso 1 1 calc GR . . . .
C15 C 0.3743(2) 0.24308(19) 0.01730(17) 0.0335(4) Uani 1 1 d . . . . .
H15 H 0.3428 0.2701 -0.0755 0.040 Uiso 1 1 calc R . . . .
C16 C 0.4800(2) 0.34655(18) 0.12939(17) 0.0315(4) Uani 1 1 d . . . . .
H16 H 0.5173 0.4421 0.1107 0.038 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 C7 1.219(2) . ?
O2 C2 1.3842(19) . ?
O2 C9 1.3752(18) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.481(2) . ?
C2 C3 1.347(2) . ?
C3 C4 1.501(2) . ?
C3 C8 1.440(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.528(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.519(2) . ?
C7 C8 1.466(2) . ?
C8 C9 1.377(2) . ?
C9 C10 1.462(2) . ?
C10 C11 1.397(2) . ?
C10 C16 1.400(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.389(2) . ?
C13 C14 1.506(2) . ?
C13 C15 1.392(2) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 0.9300 . ?
C15 C16 1.382(2) . ?
C16 H16 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
C9 O2 C2 108.21(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O2 C2 C1 116.29(15) . . ?
C3 C2 O2 109.44(14) . . ?
C3 C2 C1 134.27(15) . . ?
C2 C3 C4 128.91(15) . . ?
C2 C3 C8 107.10(14) . . ?
C8 C3 C4 123.98(15) . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
C3 C4 C5 110.09(14) . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 C4 111.66(15) . . ?
C6 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 112.80(15) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
O1 C7 C6 119.92(16) . . ?
O1 C7 C8 125.37(15) . . ?
C8 C7 C6 114.70(14) . . ?
C3 C8 C7 120.50(14) . . ?
C9 C8 C3 106.84(14) . . ?
C9 C8 C7 132.65(14) . . ?
O2 C9 C8 108.39(13) . . ?
O2 C9 C10 113.90(13) . . ?
C8 C9 C10 137.71(14) . . ?
C11 C10 C9 122.66(14) . . ?
C11 C10 C16 117.56(14) . . ?
C16 C10 C9 119.75(14) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.68(14) . . ?
C12 C11 H11 119.7 . . ?
C11 C12 H12 119.1 . . ?
C11 C12 C13 121.90(15) . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C14 121.08(15) . . ?
C12 C13 C15 117.33(14) . . ?
C15 C13 C14 121.59(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15 119.3 . . ?
C16 C15 C13 121.43(15) . . ?
C16 C15 H15 119.3 . . ?
C10 C16 H16 119.5 . . ?
C15 C16 C10 121.09(15) . . ?
C15 C16 H16 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 C7 C8 C3 -173.01(17) . . . . ?
O1 C7 C8 C9 7.2(3) . . . . ?
O2 C2 C3 C4 178.46(14) . . . . ?
O2 C2 C3 C8 -0.07(17) . . . . ?
O2 C9 C10 C11 -165.41(13) . . . . ?
O2 C9 C10 C16 12.8(2) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
C1 C2 C3 C8 -179.54(18) . . . . ?
C2 O2 C9 C8 1.27(16) . . . . ?
C2 O2 C9 C10 -178.44(12) . . . . ?
C2 C3 C4 C5 -160.71(17) . . . . ?
C2 C3 C8 C7 -178.97(14) . . . . ?
C2 C3 C8 C9 0.84(17) . . . . ?
C3 C4 C5 C6 -47.54(19) . . . . ?
C3 C8 C9 O2 -1.30(16) . . . . ?
C3 C8 C9 C10 178.32(17) . . . . ?
C4 C3 C8 C7 2.4(2) . . . . ?
C4 C3 C8 C9 -177.78(14) . . . . ?
C4 C5 C6 C7 60.4(2) . . . . ?
C5 C6 C7 O1 142.10(18) . . . . ?
C5 C6 C7 C8 -39.0(2) . . . . ?
C6 C7 C8 C3 8.2(2) . . . . ?
C6 C7 C8 C9 -171.61(16) . . . . ?
C7 C8 C9 O2 178.49(16) . . . . ?
C7 C8 C9 C10 -1.9(3) . . . . ?
C8 C3 C4 C5 17.6(2) . . . . ?
C8 C9 C10 C11 15.0(3) . . . . ?
C8 C9 C10 C16 -166.80(17) . . . . ?
C9 O2 C2 C1 178.84(14) . . . . ?
C9 O2 C2 C3 -0.74(17) . . . . ?
C9 C10 C11 C12 177.17(14) . . . . ?
C9 C10 C16 C15 -177.97(14) . . . . ?
C10 C11 C12 C13 0.9(2) . . . . ?
C11 C10 C16 C15 0.3(2) . . . . ?
C11 C12 C13 C14 179.75(15) . . . . ?
C11 C12 C13 C15 0.1(2) . . . . ?
C12 C13 C15 C16 -0.8(2) . . . . ?
C13 C15 C16 C10 0.6(2) . . . . ?
C14 C13 C15 C16 179.49(15) . . . . ?
C16 C10 C11 C12 -1.1(2) . . . . ?

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

data_exp_478
_database_code_depnum_ccdc_archive 'CCDC 1521974'
_audit_update_record             
;
2017-01-07 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H16 O2'
_chemical_formula_sum            'C23 H16 O2'
_chemical_formula_weight         324.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P  21/n '
_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                   5.58064(8)
_cell_length_b                   21.6340(3)
_cell_length_c                   13.33275(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.8686(14)
_cell_angle_gamma                90
_cell_volume                     1575.27(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5661
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.2420
_cell_measurement_theta_min      4.0740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.682
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0137
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8094
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         3.956
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -62.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788   57.0000  -60.0000 90

#__ type_ start__ end____ width___ exp.time_
  2 omega  -65.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788   57.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega -113.00  -17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.0788  -57.0000  150.0000 96

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -45.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega   42.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -94.0000  -60.0000 82

#__ type_ start__ end____ width___ exp.time_
  7 omega   52.00  121.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826 -125.0000  -90.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega   33.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -77.0000   30.0000 108

#__ type_ start__ end____ width___ exp.time_
  9 omega   93.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826   45.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -30.0000   90.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   29.00  155.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.9826  -15.0000  -30.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0102144000
_diffrn_orient_matrix_UB_12      0.0378983000
_diffrn_orient_matrix_UB_13      -0.0968958000
_diffrn_orient_matrix_UB_21      0.0787729000
_diffrn_orient_matrix_UB_22      0.0574802000
_diffrn_orient_matrix_UB_23      0.0668792000
_diffrn_orient_matrix_UB_31      0.2707069000
_diffrn_orient_matrix_UB_32      -0.0180553000
_diffrn_orient_matrix_UB_33      0.0095848000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2581
_reflns_number_total             2771
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.180
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.4190P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0914
_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 Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C18(H18), C19(H19),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 -0.04403(15) 0.57348(4) 0.63755(6) 0.0285(2) Uani 1 1 d . . . . .
O2 O 0.46558(18) 0.66509(5) 0.87690(6) 0.0430(3) Uani 1 1 d . . . . .
C1 C -0.1518(2) 0.60337(6) 0.08701(9) 0.0345(3) Uani 1 1 d . . . . .
H1 H -0.0917 0.6176 0.0311 0.041 Uiso 1 1 calc R . . . .
C2 C -0.0244(2) 0.61489(6) 0.18427(9) 0.0312(3) Uani 1 1 d . . . . .
H2 H 0.1218 0.6369 0.1939 0.037 Uiso 1 1 calc R . . . .
C3 C -0.1129(2) 0.59368(5) 0.27053(9) 0.0260(3) Uani 1 1 d . . . . .
C4 C -0.3348(2) 0.55948(5) 0.25445(9) 0.0270(3) Uani 1 1 d . . . . .
C5 C -0.4623(2) 0.54846(6) 0.15234(9) 0.0325(3) Uani 1 1 d . . . . .
H5 H -0.6080 0.5262 0.1408 0.039 Uiso 1 1 calc R . . . .
C6 C -0.3732(2) 0.57013(6) 0.07085(9) 0.0345(3) Uani 1 1 d . . . . .
H6 H -0.4593 0.5629 0.0044 0.041 Uiso 1 1 calc R . . . .
C7 C -0.4194(2) 0.53799(6) 0.34126(10) 0.0326(3) Uani 1 1 d . . . . .
H7 H -0.5633 0.5151 0.3321 0.039 Uiso 1 1 calc R . . . .
C8 C -0.2934(2) 0.55038(6) 0.43823(9) 0.0318(3) Uani 1 1 d . . . . .
H8 H -0.3526 0.5356 0.4940 0.038 Uiso 1 1 calc R . . . .
C9 C -0.0733(2) 0.58548(5) 0.45557(9) 0.0257(3) Uani 1 1 d . . . . .
C10 C 0.0130(2) 0.60625(5) 0.37178(9) 0.0269(3) Uani 1 1 d . . . . .
H10 H 0.1572 0.6291 0.3821 0.032 Uiso 1 1 calc R . . . .
C11 C 0.0543(2) 0.59977(5) 0.55962(9) 0.0260(3) Uani 1 1 d . . . . .
C12 C 0.2479(2) 0.63591(5) 0.60229(8) 0.0254(2) Uani 1 1 d . . . . .
C13 C 0.2700(2) 0.63192(5) 0.71092(9) 0.0271(3) Uani 1 1 d . . . . .
C14 C 0.0890(2) 0.59365(5) 0.72848(9) 0.0283(3) Uani 1 1 d . . . . .
C15 C 0.0119(2) 0.57192(6) 0.82232(9) 0.0345(3) Uani 1 1 d . . . . .
H15A H -0.1587 0.5809 0.8173 0.052 Uiso 1 1 calc GR . . . .
H15B H 0.1065 0.5926 0.8810 0.052 Uiso 1 1 calc GR . . . .
H15C H 0.0378 0.5281 0.8295 0.052 Uiso 1 1 calc GR . . . .
C16 C 0.4067(2) 0.67732(6) 0.55458(9) 0.0294(3) Uani 1 1 d . . . . .
H16A H 0.3050 0.7085 0.5143 0.035 Uiso 1 1 calc R . . . .
H16B H 0.4822 0.6532 0.5082 0.035 Uiso 1 1 calc R . . . .
C17 C 0.6057(2) 0.70912(5) 0.63140(9) 0.0278(3) Uani 1 1 d . . . . .
C18 C 0.7767(2) 0.74513(5) 0.59481(10) 0.0321(3) Uani 1 1 d . . . . .
H18 H 0.7645 0.7492 0.5245 0.039 Uiso 1 1 calc R . . . .
C19 C 0.9643(2) 0.77480(6) 0.66145(11) 0.0374(3) Uani 1 1 d . . . . .
H19 H 1.0763 0.7987 0.6356 0.045 Uiso 1 1 calc R . . . .
C20 C 0.9863(2) 0.76907(6) 0.76661(11) 0.0383(3) Uani 1 1 d . . . . .
H20 H 1.1132 0.7888 0.8113 0.046 Uiso 1 1 calc R . . . .
C21 C 0.8188(2) 0.73404(6) 0.80412(10) 0.0350(3) Uani 1 1 d . . . . .
H21 H 0.8333 0.7302 0.8746 0.042 Uiso 1 1 calc R . . . .
C22 C 0.6265(2) 0.70396(5) 0.73778(9) 0.0290(3) Uani 1 1 d . . . . .
C23 C 0.4527(2) 0.66646(5) 0.78394(9) 0.0300(3) 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 C11 1.3925(13) . ?
O1 C14 1.3569(14) . ?
O2 C23 1.2270(15) . ?
C1 H1 0.9300 . ?
C1 C2 1.3675(17) . ?
C1 C6 1.4071(19) . ?
C2 H2 0.9300 . ?
C2 C3 1.4179(16) . ?
C3 C4 1.4206(16) . ?
C3 C10 1.4142(16) . ?
C4 C5 1.4206(16) . ?
C4 C7 1.4154(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3674(19) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.3653(17) . ?
C8 H8 0.9300 . ?
C8 C9 1.4222(17) . ?
C9 C10 1.3795(16) . ?
C9 C11 1.4562(16) . ?
C10 H10 0.9300 . ?
C11 C12 1.3599(16) . ?
C12 C13 1.4307(15) . ?
C12 C16 1.4916(16) . ?
C13 C14 1.3631(17) . ?
C13 C23 1.4620(17) . ?
C14 C15 1.4810(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.5124(16) . ?
C17 C18 1.3956(17) . ?
C17 C22 1.4035(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.3837(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.4027(17) . ?
C22 C23 1.4907(18) . ?

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
C14 O1 C11 107.94(9) . . ?
C2 C1 H1 119.8 . . ?
C2 C1 C6 120.48(12) . . ?
C6 C1 H1 119.8 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.68(12) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 118.97(10) . . ?
C10 C3 C2 121.64(11) . . ?
C10 C3 C4 119.38(10) . . ?
C5 C4 C3 118.76(11) . . ?
C7 C4 C3 118.35(10) . . ?
C7 C4 C5 122.89(11) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.78(12) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.32(11) . . ?
C5 C6 H6 119.8 . . ?
C4 C7 H7 119.5 . . ?
C8 C7 C4 121.09(11) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.22(11) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C11 120.34(10) . . ?
C10 C9 C8 118.42(11) . . ?
C10 C9 C11 121.23(11) . . ?
C3 C10 H10 119.2 . . ?
C9 C10 C3 121.53(11) . . ?
C9 C10 H10 119.2 . . ?
O1 C11 C9 115.69(10) . . ?
C12 C11 O1 108.89(10) . . ?
C12 C11 C9 135.35(11) . . ?
C11 C12 C13 106.53(10) . . ?
C11 C12 C16 131.11(10) . . ?
C13 C12 C16 122.20(10) . . ?
C12 C13 C23 123.12(11) . . ?
C14 C13 C12 107.32(10) . . ?
C14 C13 C23 129.50(11) . . ?
O1 C14 C13 109.31(10) . . ?
O1 C14 C15 116.87(11) . . ?
C13 C14 C15 133.82(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 108.8 . . ?
C12 C16 H16B 108.8 . . ?
C12 C16 C17 113.72(10) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C17 C16 118.47(11) . . ?
C18 C17 C22 118.52(11) . . ?
C22 C17 C16 123.01(11) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.06(12) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.36(13) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.43(12) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 119.5 . . ?
C20 C21 C22 121.05(12) . . ?
C22 C21 H21 119.5 . . ?
C17 C22 C23 122.34(11) . . ?
C21 C22 C17 119.58(12) . . ?
C21 C22 C23 118.07(11) . . ?
O2 C23 C13 123.24(12) . . ?
O2 C23 C22 121.49(11) . . ?
C13 C23 C22 115.28(10) . . ?

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 C11 C12 C13 -0.10(12) . . . . ?
O1 C11 C12 C16 -175.51(11) . . . . ?
C1 C2 C3 C4 0.83(17) . . . . ?
C1 C2 C3 C10 -178.55(11) . . . . ?
C2 C1 C6 C5 -0.60(19) . . . . ?
C2 C3 C4 C5 -0.87(16) . . . . ?
C2 C3 C4 C7 179.29(10) . . . . ?
C2 C3 C10 C9 -179.89(11) . . . . ?
C3 C4 C5 C6 0.20(17) . . . . ?
C3 C4 C7 C8 0.85(18) . . . . ?
C4 C3 C10 C9 0.73(17) . . . . ?
C4 C5 C6 C1 0.54(19) . . . . ?
C4 C7 C8 C9 0.24(19) . . . . ?
C5 C4 C7 C8 -178.98(11) . . . . ?
C6 C1 C2 C3 -0.09(19) . . . . ?
C7 C4 C5 C6 -179.97(11) . . . . ?
C7 C8 C9 C10 -0.84(18) . . . . ?
C7 C8 C9 C11 178.12(11) . . . . ?
C8 C9 C10 C3 0.35(17) . . . . ?
C8 C9 C11 O1 4.25(15) . . . . ?
C8 C9 C11 C12 -172.28(12) . . . . ?
C9 C11 C12 C13 176.59(12) . . . . ?
C9 C11 C12 C16 1.2(2) . . . . ?
C10 C3 C4 C5 178.52(10) . . . . ?
C10 C3 C4 C7 -1.32(16) . . . . ?
C10 C9 C11 O1 -176.82(10) . . . . ?
C10 C9 C11 C12 6.7(2) . . . . ?
C11 O1 C14 C13 -0.18(12) . . . . ?
C11 O1 C14 C15 178.93(9) . . . . ?
C11 C9 C10 C3 -178.61(10) . . . . ?
C11 C12 C13 C14 -0.01(12) . . . . ?
C11 C12 C13 C23 -177.61(10) . . . . ?
C11 C12 C16 C17 -179.56(11) . . . . ?
C12 C13 C14 O1 0.12(13) . . . . ?
C12 C13 C14 C15 -178.78(12) . . . . ?
C12 C13 C23 O2 176.89(11) . . . . ?
C12 C13 C23 C22 -3.36(16) . . . . ?
C12 C16 C17 C18 175.03(10) . . . . ?
C12 C16 C17 C22 -4.83(16) . . . . ?
C13 C12 C16 C17 5.64(16) . . . . ?
C14 O1 C11 C9 -177.25(9) . . . . ?
C14 O1 C11 C12 0.17(12) . . . . ?
C14 C13 C23 O2 -0.1(2) . . . . ?
C14 C13 C23 C22 179.61(11) . . . . ?
C16 C12 C13 C14 175.90(10) . . . . ?
C16 C12 C13 C23 -1.70(17) . . . . ?
C16 C17 C18 C19 -179.33(11) . . . . ?
C16 C17 C22 C21 178.90(11) . . . . ?
C16 C17 C22 C23 -0.02(17) . . . . ?
C17 C18 C19 C20 0.21(19) . . . . ?
C17 C22 C23 O2 -176.05(11) . . . . ?
C17 C22 C23 C13 4.20(16) . . . . ?
C18 C17 C22 C21 -0.95(16) . . . . ?
C18 C17 C22 C23 -179.87(10) . . . . ?
C18 C19 C20 C21 -0.51(19) . . . . ?
C19 C20 C21 C22 0.06(19) . . . . ?
C20 C21 C22 C17 0.67(18) . . . . ?
C20 C21 C22 C23 179.64(11) . . . . ?
C21 C22 C23 O2 5.02(17) . . . . ?
C21 C22 C23 C13 -174.74(10) . . . . ?
C22 C17 C18 C19 0.53(17) . . . . ?
C23 C13 C14 O1 177.52(11) . . . . ?
C23 C13 C14 C15 -1.4(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dm16208
_database_code_depnum_ccdc_archive 'CCDC 1521989'
_audit_update_record             
;
2016-12-11 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H16 O2'
_chemical_formula_sum            'C20 H16 O2'
_chemical_formula_weight         288.33
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5202(9)
_cell_length_b                   22.281(4)
_cell_length_c                   11.6371(19)
_cell_angle_alpha                90
_cell_angle_beta                 90.287(3)
_cell_angle_gamma                90
_cell_volume                     1431.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4091
_cell_measurement_temperature    130
_cell_measurement_theta_max      29.91
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0438 before and 0.0352 after correction.
The Ratio of minimum to maximum transmission is 0.9039.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10161
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.991
_diffrn_reflns_theta_max         25.991
_diffrn_reflns_theta_min         0.914
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2504
_reflns_number_total             2762
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2762
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0413P)²+0.3990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0890
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8633(11) 0.1367(11)
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.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
3.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.035
;
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 0.31522(19) 0.55656(5) 0.80321(9) 0.0240(2) Uani 1 1 d . . . . .
O2 O 0.5933(2) 0.60260(5) 0.48462(9) 0.0297(3) Uani 1 1 d . . . . .
C1 C 0.2229(3) 0.53144(7) 0.60689(14) 0.0278(4) Uani 1 1 d . . . . .
H1A H 0.2956 0.4916 0.5980 0.042 Uiso 1 1 calc GR . . . .
H1B H 0.2215 0.5521 0.5325 0.042 Uiso 1 1 calc GR . . . .
H1C H 0.0565 0.5272 0.6347 0.042 Uiso 1 1 calc GR . . . .
C2 C 0.3677(3) 0.56710(7) 0.69125(13) 0.0230(3) Uani 1 1 d . . . . .
C3 C 0.5464(3) 0.60993(6) 0.68407(13) 0.0211(3) Uani 1 1 d . . . . .
C4 C 0.6562(3) 0.62795(7) 0.57413(13) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.8530(3) 0.67435(7) 0.56676(13) 0.0223(3) Uani 1 1 d . . . . .
C6 C 1.0093(3) 0.66855(7) 0.47277(13) 0.0258(3) Uani 1 1 d . . . . .
H6 H 0.9866 0.6361 0.4208 0.031 Uiso 1 1 calc R . . . .
C7 C 1.1955(3) 0.70877(8) 0.45382(14) 0.0312(4) Uani 1 1 d . . . . .
H7 H 1.3019 0.7035 0.3907 0.037 Uiso 1 1 calc R . . . .
C8 C 1.2249(3) 0.75685(8) 0.52784(15) 0.0334(4) Uani 1 1 d . . . . .
H8 H 1.3504 0.7852 0.5147 0.040 Uiso 1 1 calc R . . . .
C9 C 1.0724(3) 0.76380(7) 0.62096(14) 0.0291(4) Uani 1 1 d . . . . .
H9 H 1.0942 0.7972 0.6706 0.035 Uiso 1 1 calc R . . . .
C10 C 0.8867(3) 0.72278(7) 0.64373(13) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.7365(3) 0.73129(7) 0.75019(13) 0.0252(3) Uani 1 1 d . . . . .
H11A H 0.5638 0.7349 0.7279 0.030 Uiso 1 1 calc R . . . .
H11B H 0.7852 0.7691 0.7885 0.030 Uiso 1 1 calc R . . . .
C12 C 0.7658(3) 0.67888(7) 0.83545(13) 0.0241(3) Uani 1 1 d . . . . .
H12A H 0.9368 0.6654 0.8366 0.029 Uiso 1 1 calc R . . . .
H12B H 0.7232 0.6925 0.9137 0.029 Uiso 1 1 calc R . . . .
C13 C 0.6048(3) 0.62741(7) 0.80120(13) 0.0214(3) Uani 1 1 d . . . . .
C14 C 0.4631(3) 0.59319(7) 0.87047(13) 0.0219(3) Uani 1 1 d . . . . .
C15 C 0.4273(3) 0.58688(7) 0.99456(13) 0.0224(3) Uani 1 1 d . . . . .
C16 C 0.5991(3) 0.60707(7) 1.07512(14) 0.0267(3) Uani 1 1 d . . . . .
H16 H 0.7454 0.6249 1.0493 0.032 Uiso 1 1 calc R . . . .
C17 C 0.5570(3) 0.60124(7) 1.19215(14) 0.0295(4) Uani 1 1 d . . . . .
H17 H 0.6728 0.6161 1.2457 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3482(3) 0.57398(7) 1.23152(14) 0.0293(4) Uani 1 1 d . . . . .
H18 H 0.3212 0.5696 1.3116 0.035 Uiso 1 1 calc R . . . .
C19 C 0.1782(3) 0.55303(8) 1.15242(14) 0.0315(4) Uani 1 1 d . . . . .
H19 H 0.0352 0.5338 1.1788 0.038 Uiso 1 1 calc R . . . .
C20 C 0.2158(3) 0.55995(7) 1.03519(14) 0.0278(4) Uani 1 1 d . . . . .
H20 H 0.0966 0.5463 0.9822 0.033 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 C2 1.3566(18) . ?
O1 C14 1.3924(18) . ?
O2 C4 1.2332(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.492(2) . ?
C2 C3 1.375(2) . ?
C3 C4 1.474(2) . ?
C3 C13 1.452(2) . ?
C4 C5 1.503(2) . ?
C5 C6 1.402(2) . ?
C5 C10 1.414(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.400(2) . ?
C10 C11 1.506(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.540(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.503(2) . ?
C13 C14 1.360(2) . ?
C14 C15 1.465(2) . ?
C15 C16 1.404(2) . ?
C15 C20 1.397(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.383(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.392(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.390(2) . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C14 108.13(12) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
O1 C2 C1 115.06(13) . . ?
O1 C2 C3 109.57(13) . . ?
C3 C2 C1 135.37(14) . . ?
C2 C3 C4 122.67(13) . . ?
C2 C3 C13 106.57(13) . . ?
C13 C3 C4 130.63(14) . . ?
O2 C4 C3 119.55(14) . . ?
O2 C4 C5 117.87(14) . . ?
C3 C4 C5 122.51(13) . . ?
C6 C5 C4 115.40(14) . . ?
C6 C5 C10 119.02(14) . . ?
C10 C5 C4 125.55(14) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 C5 121.70(15) . . ?
C7 C6 H6 119.1 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.20(16) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.25(16) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.61(16) . . ?
C10 C9 H9 119.2 . . ?
C5 C10 C11 123.11(14) . . ?
C9 C10 C5 118.18(15) . . ?
C9 C10 C11 118.69(14) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C10 C11 C12 112.20(13) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C13 C12 C11 110.33(12) . . ?
C13 C12 H12A 109.6 . . ?
C13 C12 H12B 109.6 . . ?
C3 C13 C12 125.56(13) . . ?
C14 C13 C3 106.27(13) . . ?
C14 C13 C12 127.70(14) . . ?
O1 C14 C15 114.59(13) . . ?
C13 C14 O1 109.44(13) . . ?
C13 C14 C15 135.96(14) . . ?
C16 C15 C14 122.22(14) . . ?
C20 C15 C14 119.46(14) . . ?
C20 C15 C16 118.32(14) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.60(15) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.64(15) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.25(15) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.55(16) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 H20 119.7 . . ?
C19 C20 C15 120.62(15) . . ?
C19 C20 H20 119.7 . . ?

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 C2 C3 C4 175.31(13) . . . . ?
O1 C2 C3 C13 -0.83(16) . . . . ?
O1 C14 C15 C16 162.42(14) . . . . ?
O1 C14 C15 C20 -17.6(2) . . . . ?
O2 C4 C5 C6 -23.9(2) . . . . ?
O2 C4 C5 C10 154.33(15) . . . . ?
C1 C2 C3 C4 -5.3(3) . . . . ?
C1 C2 C3 C13 178.55(17) . . . . ?
C2 O1 C14 C13 1.10(16) . . . . ?
C2 O1 C14 C15 179.98(13) . . . . ?
C2 C3 C4 O2 -2.6(2) . . . . ?
C2 C3 C4 C5 -179.40(14) . . . . ?
C2 C3 C13 C12 -171.22(14) . . . . ?
C2 C3 C13 C14 1.47(17) . . . . ?
C3 C4 C5 C6 152.95(14) . . . . ?
C3 C4 C5 C10 -28.8(2) . . . . ?
C3 C13 C14 O1 -1.57(17) . . . . ?
C3 C13 C14 C15 179.90(17) . . . . ?
C4 C3 C13 C12 13.1(3) . . . . ?
C4 C3 C13 C14 -174.25(15) . . . . ?
C4 C5 C6 C7 178.64(14) . . . . ?
C4 C5 C10 C9 -176.77(14) . . . . ?
C4 C5 C10 C11 4.8(2) . . . . ?
C5 C6 C7 C8 -1.6(2) . . . . ?
C5 C10 C11 C12 62.02(19) . . . . ?
C6 C5 C10 C9 1.4(2) . . . . ?
C6 C5 C10 C11 -176.97(14) . . . . ?
C6 C7 C8 C9 1.2(2) . . . . ?
C7 C8 C9 C10 0.5(2) . . . . ?
C8 C9 C10 C5 -1.8(2) . . . . ?
C8 C9 C10 C11 176.65(15) . . . . ?
C9 C10 C11 C12 -116.39(15) . . . . ?
C10 C5 C6 C7 0.3(2) . . . . ?
C10 C11 C12 C13 -82.16(16) . . . . ?
C11 C12 C13 C3 34.9(2) . . . . ?
C11 C12 C13 C14 -136.20(16) . . . . ?
C12 C13 C14 O1 170.92(14) . . . . ?
C12 C13 C14 C15 -7.6(3) . . . . ?
C13 C3 C4 O2 172.55(15) . . . . ?
C13 C3 C4 C5 -4.3(2) . . . . ?
C13 C14 C15 C16 -19.1(3) . . . . ?
C13 C14 C15 C20 160.88(18) . . . . ?
C14 O1 C2 C1 -179.64(13) . . . . ?
C14 O1 C2 C3 -0.12(16) . . . . ?
C14 C15 C16 C17 178.90(15) . . . . ?
C14 C15 C20 C19 179.53(15) . . . . ?
C15 C16 C17 C18 1.8(2) . . . . ?
C16 C15 C20 C19 -0.5(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C20 -0.7(3) . . . . ?
C18 C19 C20 C15 1.4(3) . . . . ?
C20 C15 C16 C17 -1.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8633(11)
2 0.1367(11)

