# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_187
_database_code_depnum_ccdc_archive 'CCDC 1524750'
_audit_update_record             
;
2016-12-28 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;
_audit_creation_date             2016-12-27
_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         'C26 H27 N O3'
_chemical_formula_sum            'C26 H27 N O3'
_chemical_formula_weight         401.48
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.2089(3)
_cell_length_b                   10.5763(4)
_cell_length_c                   10.9769(4)
_cell_angle_alpha                100.503(3)
_cell_angle_beta                 95.221(3)
_cell_angle_gamma                91.160(3)
_cell_volume                     1046.09(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5013
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5150
_cell_measurement_theta_min      4.2420
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.853
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77654
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6974
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.640
_diffrn_reflns_theta_min         4.115
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9912
_diffrn_measured_fraction_theta_max 0.9622
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  47.00   1.00    1.00    --   40.98 -99.00   0.00   46
  2  ω      6.00  34.00   1.00    1.00    --   40.98-103.00  44.00   28
  3  ω      2.00  69.00   1.00    1.00    --   40.98 -99.00  90.00   67
  4  ω     31.00 122.00   1.00    1.00    --  106.95 -30.00 150.00   91
  5  ω     57.00 117.00   1.00    1.00    --  106.95 -30.00  30.00   60
  6  ω     80.00 178.00   1.00    1.00    --  106.95  30.00 -30.00   98
  7  ω    121.00 173.00   1.00    1.00    --  106.95  30.00-150.00   52
  8  ω    120.00 175.00   1.00    1.00    --  106.95 125.00-180.00   55
  9  ω     94.00 123.00   1.00    1.00    --  106.95 125.00-150.00   29
 10  ω     63.00 123.00   1.00    1.00    --  106.95 -45.00 -90.00   60
 11  ω    104.00 140.00   1.00    1.00    --  106.95 -77.00-150.00   36
 12  ω     55.00  82.00   1.00    1.00    --  106.95 -77.00-150.00   27
 13  ω     49.00 101.00   1.00    1.00    --  106.95 -94.00 -90.00   52
 14  ω     34.00 109.00   1.00    1.00    --  106.95 -94.00-180.00   75
 15  ω     33.00  78.00   1.00    1.00    --   40.98 -99.00-120.00   45
 16  ω     69.00 120.00   1.00    1.00    --  106.95-125.00  60.00   51
 17  ω     24.00  95.00   1.00    1.00    --  106.95 -94.00 120.00   71
 18  ω   -108.00 -17.00   1.00    1.00    --  -40.98 -37.00-150.00   91
 19  ω   -114.00 -36.00   1.00    1.00    --  -40.98 -37.00 120.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1154897000
_diffrn_orient_matrix_UB_12      0.1009037000
_diffrn_orient_matrix_UB_13      -0.0146590000
_diffrn_orient_matrix_UB_21      0.0396325000
_diffrn_orient_matrix_UB_22      0.0658205000
_diffrn_orient_matrix_UB_23      0.1365197000
_diffrn_orient_matrix_UB_31      0.1155475000
_diffrn_orient_matrix_UB_32      0.0863925000
_diffrn_orient_matrix_UB_33      -0.0413799000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus 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                3797
_reflns_number_total             4070
_reflns_odcompleteness_completeness 99.12
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.343
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4070
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.044
_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)+(0.0527P)²+0.3612P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C3(H3), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C24(H24A,H24B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C16(H16), C13(H13), C10(H10), C17(H17), C15(H15), C14(H14),
 C9(H9), C23(H23), C19(H19), C20(H20), C22(H22), C21(H21)
2.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C)
;
_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 0.46359(9) 0.82172(8) 0.20503(8) 0.02236(19) Uani 1 1 d . . . . .
O2 O 0.80087(10) 0.70725(9) 0.49753(9) 0.0271(2) Uani 1 1 d . . . . .
O3 O 0.22776(10) 0.67061(9) 0.73014(9) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.32527(12) 0.46543(10) 0.28713(10) 0.0247(2) Uani 1 1 d . . . . .
H1 H 0.3341 0.4268 0.3498 0.030 Uiso 1 1 calc R . . . .
C12 C 0.88343(13) 0.85872(11) 0.38249(11) 0.0200(2) Uani 1 1 d . . . . .
C18 C 0.25542(13) 0.40071(11) 0.17566(11) 0.0215(2) Uani 1 1 d . . . . .
C5 C 0.50543(12) 0.76344(11) 0.47734(11) 0.0200(2) Uani 1 1 d . . . . .
C6 C 0.40222(13) 0.66202(11) 0.43770(11) 0.0206(2) Uani 1 1 d . . . . .
C11 C 0.76819(13) 0.78567(11) 0.43209(11) 0.0208(2) Uani 1 1 d . . . . .
C8 C 0.31626(13) 0.69496(12) 0.64276(12) 0.0235(3) Uani 1 1 d . . . . .
C7 C 0.30792(13) 0.62837(12) 0.52107(12) 0.0223(3) Uani 1 1 d . . . . .
H7 H 0.2394 0.5609 0.4945 0.027 Uiso 1 1 calc R . . . .
C4 C 0.60838(12) 0.80889(11) 0.39274(11) 0.0203(2) Uani 1 1 d . . . . .
H4 H 0.5987 0.9020 0.3997 0.024 Uiso 1 1 calc R . . . .
C3 C 0.57494(13) 0.74735(12) 0.25423(11) 0.0216(2) Uani 1 1 d . . . . .
H3 H 0.6627 0.7531 0.2110 0.026 Uiso 1 1 calc R . . . .
C1 C 0.38413(13) 0.59609(11) 0.30198(11) 0.0213(2) Uani 1 1 d . . . . .
H1A H 0.3119 0.6439 0.2593 0.026 Uiso 1 1 calc R . . . .
C16 C 1.13676(13) 0.88376(12) 0.34797(12) 0.0248(3) Uani 1 1 d . . . . .
H16 H 1.2320 0.8565 0.3547 0.030 Uiso 1 1 calc R . . . .
C13 C 0.85262(14) 0.96546(12) 0.32699(12) 0.0241(3) Uani 1 1 d . . . . .
H13 H 0.7574 0.9928 0.3194 0.029 Uiso 1 1 calc R . . . .
C10 C 0.51218(13) 0.82846(12) 0.60062(12) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.5802 0.8962 0.6277 0.028 Uiso 1 1 calc R . . . .
C17 C 1.02677(13) 0.81923(12) 0.39296(11) 0.0231(3) Uani 1 1 d . . . . .
H17 H 1.0488 0.7490 0.4304 0.028 Uiso 1 1 calc R . . . .
C15 C 1.10431(14) 0.98891(12) 0.29306(11) 0.0236(3) Uani 1 1 d . . . . .
H15 H 1.1781 1.0318 0.2625 0.028 Uiso 1 1 calc R . . . .
C14 C 0.96279(14) 1.03084(12) 0.28317(12) 0.0253(3) Uani 1 1 d . . . . .
H14 H 0.9419 1.1024 0.2474 0.030 Uiso 1 1 calc R . . . .
C9 C 0.42069(14) 0.79482(12) 0.68328(12) 0.0247(3) Uani 1 1 d . . . . .
H9 H 0.4286 0.8384 0.7654 0.030 Uiso 1 1 calc R . . . .
C2 C 0.52651(13) 0.60631(12) 0.24188(11) 0.0229(3) Uani 1 1 d . . . . .
H2A H 0.6018 0.5610 0.2822 0.027 Uiso 1 1 calc R . . . .
H2B H 0.5121 0.5665 0.1546 0.027 Uiso 1 1 calc R . . . .
C23 C 0.21346(14) 0.27059(12) 0.16521(12) 0.0246(3) Uani 1 1 d . . . . .
H23 H 0.2383 0.2287 0.2313 0.029 Uiso 1 1 calc R . . . .
C19 C 0.21801(14) 0.45987(12) 0.07372(12) 0.0263(3) Uani 1 1 d . . . . .
H19 H 0.2458 0.5456 0.0772 0.032 Uiso 1 1 calc R . . . .
C24 C 0.44803(15) 0.80245(14) 0.07194(12) 0.0298(3) Uani 1 1 d . . . . .
H24A H 0.4219 0.7130 0.0370 0.036 Uiso 1 1 calc R . . . .
H24B H 0.5390 0.8248 0.0416 0.036 Uiso 1 1 calc R . . . .
C20 C 0.13944(15) 0.39121(13) -0.03273(12) 0.0290(3) Uani 1 1 d . . . . .
H20 H 0.1149 0.4321 -0.0995 0.035 Uiso 1 1 calc R . . . .
C22 C 0.13585(14) 0.20356(12) 0.05845(12) 0.0269(3) Uani 1 1 d . . . . .
H22 H 0.1094 0.1173 0.0536 0.032 Uiso 1 1 calc R . . . .
C21 C 0.09694(14) 0.26338(13) -0.04157(12) 0.0277(3) Uani 1 1 d . . . . .
H21 H 0.0435 0.2186 -0.1129 0.033 Uiso 1 1 calc R . . . .
C26 C 0.10040(14) 0.58886(13) 0.68709(13) 0.0304(3) Uani 1 1 d . . . . .
H26A H 0.0437 0.6224 0.6232 0.046 Uiso 1 1 calc GR . . . .
H26B H 0.0429 0.5857 0.7552 0.046 Uiso 1 1 calc GR . . . .
H26C H 0.1293 0.5037 0.6540 0.046 Uiso 1 1 calc GR . . . .
C25 C 0.32931(17) 0.88796(17) 0.03485(13) 0.0392(4) Uani 1 1 d . . . . .
H25A H 0.3149 0.8764 -0.0543 0.059 Uiso 1 1 calc GR . . . .
H25B H 0.3571 0.9762 0.0688 0.059 Uiso 1 1 calc GR . . . .
H25C H 0.2402 0.8657 0.0664 0.059 Uiso 1 1 calc GR . . . .


_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 1.4313(14) . ?
O1 C24 1.4312(15) . ?
O2 C11 1.2175(15) . ?
O3 C8 1.3691(15) . ?
O3 C26 1.4337(16) . ?
N1 H1 0.8600 . ?
N1 C18 1.3831(16) . ?
N1 C1 1.4497(15) . ?
C12 C11 1.4983(16) . ?
C12 C13 1.3994(17) . ?
C12 C17 1.3936(17) . ?
C18 C23 1.4033(17) . ?
C18 C19 1.3985(17) . ?
C5 C6 1.3988(16) . ?
C5 C4 1.5155(16) . ?
C5 C10 1.3970(17) . ?
C6 C7 1.4031(17) . ?
C6 C1 1.5182(16) . ?
C11 C4 1.5331(16) . ?
C8 C7 1.3865(18) . ?
C8 C9 1.3957(18) . ?
C7 H7 0.9300 . ?
C4 H4 0.9800 . ?
C4 C3 1.5414(16) . ?
C3 H3 0.9800 . ?
C3 C2 1.5267(16) . ?
C1 H1A 0.9800 . ?
C1 C2 1.5309(16) . ?
C16 H16 0.9300 . ?
C16 C17 1.3862(17) . ?
C16 C15 1.3836(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3858(17) . ?
C10 H10 0.9300 . ?
C10 C9 1.3800(17) . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.3864(18) . ?
C14 H14 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C22 1.3824(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3899(18) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.5074(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.3836(19) . ?
C22 H22 0.9300 . ?
C22 C21 1.3874(19) . ?
C21 H21 0.9300 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

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
C24 O1 C3 113.59(9) . . ?
C8 O3 C26 117.33(10) . . ?
C18 N1 H1 118.9 . . ?
C18 N1 C1 122.25(10) . . ?
C1 N1 H1 118.9 . . ?
C13 C12 C11 122.47(11) . . ?
C17 C12 C11 118.63(11) . . ?
C17 C12 C13 118.90(11) . . ?
N1 C18 C23 118.85(11) . . ?
N1 C18 C19 123.30(11) . . ?
C19 C18 C23 117.78(11) . . ?
C6 C5 C4 123.47(11) . . ?
C10 C5 C6 118.49(11) . . ?
C10 C5 C4 118.02(10) . . ?
C5 C6 C7 119.91(11) . . ?
C5 C6 C1 119.80(10) . . ?
C7 C6 C1 120.09(11) . . ?
O2 C11 C12 120.92(11) . . ?
O2 C11 C4 121.40(10) . . ?
C12 C11 C4 117.62(10) . . ?
O3 C8 C7 124.73(12) . . ?
O3 C8 C9 115.46(11) . . ?
C7 C8 C9 119.82(11) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.47(11) . . ?
C8 C7 H7 119.8 . . ?
C5 C4 C11 112.10(10) . . ?
C5 C4 H4 107.5 . . ?
C5 C4 C3 114.01(10) . . ?
C11 C4 H4 107.5 . . ?
C11 C4 C3 108.08(9) . . ?
C3 C4 H4 107.5 . . ?
O1 C3 C4 106.14(9) . . ?
O1 C3 H3 109.5 . . ?
O1 C3 C2 112.28(10) . . ?
C4 C3 H3 109.5 . . ?
C2 C3 C4 109.99(10) . . ?
C2 C3 H3 109.5 . . ?
N1 C1 C6 111.66(10) . . ?
N1 C1 H1A 106.8 . . ?
N1 C1 C2 113.66(10) . . ?
C6 C1 H1A 106.8 . . ?
C6 C1 C2 110.69(10) . . ?
C2 C1 H1A 106.8 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.78(12) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.57(12) . . ?
C14 C13 H13 119.7 . . ?
C5 C10 H10 119.1 . . ?
C9 C10 C5 121.80(11) . . ?
C9 C10 H10 119.1 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.57(11) . . ?
C16 C17 H17 119.7 . . ?
C16 C15 H15 119.7 . . ?
C16 C15 C14 120.60(11) . . ?
C14 C15 H15 119.7 . . ?
C13 C14 C15 119.59(11) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C8 C9 H9 120.2 . . ?
C10 C9 C8 119.50(12) . . ?
C10 C9 H9 120.2 . . ?
C3 C2 C1 110.10(10) . . ?
C3 C2 H2A 109.6 . . ?
C3 C2 H2B 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.2 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.14(12) . . ?
C22 C23 H23 119.4 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.33(12) . . ?
C20 C19 H19 119.8 . . ?
O1 C24 H24A 110.3 . . ?
O1 C24 H24B 110.3 . . ?
O1 C24 C25 107.26(11) . . ?
H24A C24 H24B 108.5 . . ?
C25 C24 H24A 110.3 . . ?
C25 C24 H24B 110.3 . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.47(12) . . ?
C21 C20 H20 119.3 . . ?
C23 C22 H22 119.6 . . ?
C23 C22 C21 120.80(12) . . ?
C21 C22 H22 119.6 . . ?
C20 C21 C22 118.47(12) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.636
####################################################################### 
# 
# 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_106-4-2
_database_code_depnum_ccdc_archive 'CCDC 1589273'
_audit_update_record             
;
2017-12-05 deposited with the CCDC.
2018-01-24 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 F O2'
_chemical_formula_sum            'C23 H19 F O2'
_chemical_formula_weight         346.38
_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'
F F 0.0171 0.0103 '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      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                   8.9683(5)
_cell_length_b                   9.8217(5)
_cell_length_c                   11.3530(7)
_cell_angle_alpha                75.074(5)
_cell_angle_beta                 77.458(5)
_cell_angle_gamma                63.345(5)
_cell_volume                     857.58(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4595
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.2160
_cell_measurement_theta_min      2.5600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60428
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.880
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14359
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.529
_diffrn_reflns_theta_min         2.360
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.880
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  84.00   1.00    1.00    --   11.74  57.00   0.00   69
  2  ω     44.00  86.00   1.00    1.00    --   11.74  37.00 -60.00   42
  3  ω    -12.00  84.00   1.00    1.00    --   11.74  37.00 120.00   96
  4  ω    -18.00  53.00   1.00    1.00    --   11.74 -99.00  60.00   71
  5  ω    -46.00  40.00   1.00    1.00    --   11.74 -57.00 -60.00   86
  6  ω    -20.00  53.00   1.00    1.00    --   11.74 -99.00-180.00   73
  7  ω    -19.00  86.00   1.00    1.00    --   11.74  77.00-150.00  105
  8  ω     37.00  77.00   1.00    1.00    --   11.74 178.00 -30.00   40
  9  ω    -83.00 -52.00   1.00    1.00    --  -11.59 149.00 149.62   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0695997000
_diffrn_orient_matrix_UB_12      -0.0094415000
_diffrn_orient_matrix_UB_13      0.0387030000
_diffrn_orient_matrix_UB_21      0.0334388000
_diffrn_orient_matrix_UB_22      -0.0022634000
_diffrn_orient_matrix_UB_23      0.0520006000
_diffrn_orient_matrix_UB_31      -0.0444862000
_diffrn_orient_matrix_UB_32      0.0816270000
_diffrn_orient_matrix_UB_33      -0.0061180000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3211
_reflns_number_total             4222
_reflns_odcompleteness_completeness 99.97
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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         0.284
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.034
_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)+(0.0471P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1198
_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:
 C7(H7), C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C17(H17), C4(H4), C19(H19), C14(H14), C1(H1A), C2(H2), C16(H16),
 C20(H20), C15(H15), C23(H23), C3(H3), C22(H22)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
F1 F -0.16477(12) 0.83937(12) 0.93987(8) 0.0359(3) Uani 1 1 d . . . . .
O1 O 0.36184(13) 0.80431(12) 0.24443(9) 0.0204(2) Uani 1 1 d . . . . .
H1 H 0.379098 0.718041 0.285954 0.031 Uiso 1 1 calc GR . . . .
O2 O 0.61011(14) 0.49325(12) 0.62594(10) 0.0245(3) Uani 1 1 d . . . . .
C11 C 0.57183(17) 0.61579(16) 0.65809(13) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.59432(18) 0.61712(16) 0.78365(13) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.62861(18) 0.76009(16) 0.44985(13) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.57690(18) 0.81845(16) 0.33215(13) 0.0167(3) Uani 1 1 d . . . . .
C7 C 0.39352(18) 0.89269(16) 0.31024(13) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.372665 0.994128 0.257477 0.021 Uiso 1 1 calc R . . . .
C13 C 0.51986(18) 0.75095(17) 0.83514(13) 0.0192(3) Uani 1 1 d . . . . .
H13 H 0.456665 0.845448 0.788849 0.023 Uiso 1 1 calc R . . . .
C18 C 0.20138(18) 0.79569(17) 0.64305(13) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.50140(18) 0.76514(16) 0.56444(13) 0.0167(3) Uani 1 1 d . . . . .
H10 H 0.479974 0.853523 0.600737 0.020 Uiso 1 1 calc R . . . .
C17 C 0.69031(18) 0.47641(17) 0.85461(13) 0.0185(3) Uani 1 1 d . . . . .
H17 H 0.738923 0.386154 0.822028 0.022 Uiso 1 1 calc R . . . .
C4 C 0.80031(19) 0.69597(16) 0.46148(14) 0.0196(3) Uani 1 1 d . . . . .
H4 H 0.835086 0.661056 0.539397 0.023 Uiso 1 1 calc R . . . .
C9 C 0.33386(18) 0.78230(16) 0.53260(13) 0.0166(3) Uani 1 1 d . . . . .
H9 H 0.356313 0.689361 0.502177 0.020 Uiso 1 1 calc R . . . .
C19 C 0.14310(18) 0.91856(17) 0.70518(13) 0.0198(3) Uani 1 1 d . . . . .
H19 H 0.187833 0.991875 0.678993 0.024 Uiso 1 1 calc R . . . .
C14 C 0.53951(19) 0.74390(18) 0.95462(14) 0.0222(3) Uani 1 1 d . . . . .
H14 H 0.487008 0.832864 0.989054 0.027 Uiso 1 1 calc R . . . .
C8 C 0.27482(18) 0.92169(17) 0.42815(13) 0.0184(3) Uani 1 1 d . . . . .
H8A H 0.163141 0.942301 0.414033 0.022 Uiso 1 1 calc R . . . .
H8B H 0.268486 1.012466 0.451750 0.022 Uiso 1 1 calc R . . . .
C1 C 0.69876(19) 0.80511(16) 0.23001(14) 0.0194(3) Uani 1 1 d . . . . .
H1A H 0.664945 0.843172 0.151766 0.023 Uiso 1 1 calc R . . . .
C2 C 0.86812(19) 0.73678(17) 0.24252(14) 0.0223(3) Uani 1 1 d . . . . .
H2 H 0.947225 0.726509 0.173345 0.027 Uiso 1 1 calc R . . . .
C16 C 0.71349(19) 0.47035(18) 0.97245(14) 0.0219(3) Uani 1 1 d . . . . .
H16 H 0.779912 0.376828 1.018086 0.026 Uiso 1 1 calc R . . . .
C21 C -0.04434(19) 0.82467(19) 0.84089(14) 0.0244(4) Uani 1 1 d . . . . .
C20 C 0.02020(19) 0.93426(18) 0.80497(14) 0.0227(3) Uani 1 1 d . . . . .
H20 H -0.017440 1.016236 0.846346 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6376(2) 0.60398(18) 1.02284(14) 0.0228(3) Uani 1 1 d . . . . .
H15 H 0.652498 0.599651 1.102479 0.027 Uiso 1 1 calc R . . . .
C23 C 0.1319(2) 0.68768(18) 0.68329(14) 0.0229(3) Uani 1 1 d . . . . .
H23 H 0.169347 0.604807 0.642957 0.027 Uiso 1 1 calc R . . . .
C3 C 0.91963(19) 0.68345(17) 0.35919(14) 0.0223(3) Uani 1 1 d . . . . .
H3 H 1.033242 0.639700 0.368586 0.027 Uiso 1 1 calc R . . . .
C22 C 0.0074(2) 0.7018(2) 0.78285(15) 0.0266(4) Uani 1 1 d . . . . .
H22 H -0.039287 0.629983 0.809260 0.032 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
F1 C21 1.3662(17) . ?
O1 H1 0.8200 . ?
O1 C7 1.4284(17) . ?
O2 C11 1.2250(17) . ?
C11 C12 1.487(2) . ?
C11 C10 1.5291(19) . ?
C12 C13 1.398(2) . ?
C12 C17 1.400(2) . ?
C5 C6 1.402(2) . ?
C5 C10 1.5278(19) . ?
C5 C4 1.400(2) . ?
C6 C7 1.519(2) . ?
C6 C1 1.398(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.5204(19) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C18 C9 1.5162(19) . ?
C18 C19 1.393(2) . ?
C18 C23 1.393(2) . ?
C10 H10 0.9800 . ?
C10 C9 1.547(2) . ?
C17 H17 0.9300 . ?
C17 C16 1.380(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.387(2) . ?
C9 H9 0.9800 . ?
C9 C8 1.5320(19) . ?
C19 H19 0.9300 . ?
C19 C20 1.385(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.387(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C1 H1A 0.9300 . ?
C1 C2 1.381(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.389(2) . ?
C21 C20 1.375(2) . ?
C21 C22 1.371(2) . ?
C20 H20 0.9300 . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
C23 C22 1.392(2) . ?
C3 H3 0.9300 . ?
C22 H22 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
C7 O1 H1 109.5 . . ?
O2 C11 C12 120.58(13) . . ?
O2 C11 C10 117.50(13) . . ?
C12 C11 C10 121.92(12) . . ?
C13 C12 C11 123.08(13) . . ?
C13 C12 C17 118.76(13) . . ?
C17 C12 C11 118.12(13) . . ?
C6 C5 C10 121.20(12) . . ?
C4 C5 C6 118.89(13) . . ?
C4 C5 C10 119.91(13) . . ?
C5 C6 C7 122.79(13) . . ?
C1 C6 C5 118.96(13) . . ?
C1 C6 C7 118.23(12) . . ?
O1 C7 C6 110.65(11) . . ?
O1 C7 H7 107.0 . . ?
O1 C7 C8 112.49(12) . . ?
C6 C7 H7 107.0 . . ?
C6 C7 C8 112.39(12) . . ?
C8 C7 H7 107.0 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.50(14) . . ?
C14 C13 H13 119.7 . . ?
C19 C18 C9 120.74(13) . . ?
C19 C18 C23 118.27(14) . . ?
C23 C18 C9 120.98(13) . . ?
C11 C10 H10 109.1 . . ?
C11 C10 C9 108.68(11) . . ?
C5 C10 C11 109.81(11) . . ?
C5 C10 H10 109.1 . . ?
C5 C10 C9 111.06(11) . . ?
C9 C10 H10 109.1 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.65(14) . . ?
C16 C17 H17 119.7 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.37(14) . . ?
C3 C4 H4 119.3 . . ?
C18 C9 C10 112.61(12) . . ?
C18 C9 H9 107.9 . . ?
C18 C9 C8 112.13(11) . . ?
C10 C9 H9 107.9 . . ?
C8 C9 C10 108.23(11) . . ?
C8 C9 H9 107.9 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.62(14) . . ?
C20 C19 H19 119.2 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.94(15) . . ?
C15 C14 H14 120.0 . . ?
C7 C8 C9 111.40(12) . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C6 C1 H1A 119.2 . . ?
C2 C1 C6 121.59(14) . . ?
C2 C1 H1A 119.2 . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.59(14) . . ?
C3 C2 H2 120.2 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 119.97(14) . . ?
C15 C16 H16 120.0 . . ?
F1 C21 C20 117.89(15) . . ?
F1 C21 C22 118.97(14) . . ?
C22 C21 C20 123.13(14) . . ?
C19 C20 H20 121.1 . . ?
C21 C20 C19 117.81(15) . . ?
C21 C20 H20 121.1 . . ?
C14 C15 C16 120.15(14) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C18 C23 H23 119.5 . . ?
C22 C23 C18 121.07(15) . . ?
C22 C23 H23 119.5 . . ?
C4 C3 C2 119.52(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C21 C22 C23 118.09(15) . . ?
C21 C22 H22 121.0 . . ?
C23 C22 H22 121.0 . . ?

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
F1 C21 C20 C19 179.55(13) . . . . ?
F1 C21 C22 C23 -179.11(13) . . . . ?
O1 C7 C8 C9 81.91(15) . . . . ?
O2 C11 C12 C13 -165.20(14) . . . . ?
O2 C11 C12 C17 12.7(2) . . . . ?
O2 C11 C10 C5 -58.51(17) . . . . ?
O2 C11 C10 C9 63.16(16) . . . . ?
C11 C12 C13 C14 177.24(14) . . . . ?
C11 C12 C17 C16 -179.11(13) . . . . ?
C11 C10 C9 C18 61.92(15) . . . . ?
C11 C10 C9 C8 -173.55(11) . . . . ?
C12 C11 C10 C5 121.30(14) . . . . ?
C12 C11 C10 C9 -117.03(14) . . . . ?
C12 C13 C14 C15 1.8(2) . . . . ?
C12 C17 C16 C15 1.7(2) . . . . ?
C5 C6 C7 O1 -116.55(14) . . . . ?
C5 C6 C7 C8 10.14(19) . . . . ?
C5 C6 C1 C2 -0.4(2) . . . . ?
C5 C10 C9 C18 -177.18(11) . . . . ?
C5 C10 C9 C8 -52.65(15) . . . . ?
C5 C4 C3 C2 0.6(2) . . . . ?
C6 C5 C10 C11 140.91(13) . . . . ?
C6 C5 C10 C9 20.68(18) . . . . ?
C6 C5 C4 C3 -2.7(2) . . . . ?
C6 C7 C8 C9 -43.78(16) . . . . ?
C6 C1 C2 C3 -1.8(2) . . . . ?
C7 C6 C1 C2 -178.98(13) . . . . ?
C13 C12 C17 C16 -1.1(2) . . . . ?
C13 C14 C15 C16 -1.2(2) . . . . ?
C18 C9 C8 C7 -168.94(12) . . . . ?
C18 C19 C20 C21 -0.5(2) . . . . ?
C18 C23 C22 C21 -0.4(2) . . . . ?
C10 C11 C12 C13 15.0(2) . . . . ?
C10 C11 C12 C17 -167.12(13) . . . . ?
C10 C5 C6 C7 1.2(2) . . . . ?
C10 C5 C6 C1 -177.31(12) . . . . ?
C10 C5 C4 C3 177.16(13) . . . . ?
C10 C9 C8 C7 66.24(15) . . . . ?
C17 C12 C13 C14 -0.6(2) . . . . ?
C17 C16 C15 C14 -0.5(2) . . . . ?
C4 C5 C6 C7 -178.89(13) . . . . ?
C4 C5 C6 C1 2.6(2) . . . . ?
C4 C5 C10 C11 -38.95(18) . . . . ?
C4 C5 C10 C9 -159.18(13) . . . . ?
C9 C18 C19 C20 178.92(13) . . . . ?
C9 C18 C23 C22 -178.46(13) . . . . ?
C19 C18 C9 C10 61.58(17) . . . . ?
C19 C18 C9 C8 -60.78(18) . . . . ?
C19 C18 C23 C22 0.1(2) . . . . ?
C1 C6 C7 O1 62.02(16) . . . . ?
C1 C6 C7 C8 -171.30(12) . . . . ?
C1 C2 C3 C4 1.7(2) . . . . ?
C20 C21 C22 C23 0.3(2) . . . . ?
C23 C18 C9 C10 -119.95(15) . . . . ?
C23 C18 C9 C8 117.69(15) . . . . ?
C23 C18 C19 C20 0.4(2) . . . . ?
C22 C21 C20 C19 0.1(2) . . . . ?


_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.479
