# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_dt1716a_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1560816'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 O'
_chemical_formula_sum            'C19 H16 O'
_chemical_formula_weight         260.32
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.482
_cell_length_b                   5.173
_cell_length_c                   12.755
_cell_angle_alpha                90
_cell_angle_beta                 98.46
_cell_angle_gamma                90
_cell_volume                     684.1
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3400
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0567 before and 0.0501 after correction. The Ratio of minimum to maximum transmission is 0.9387. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             276
_exptl_crystal_preparation       'Takeda Reaction'
_exptl_crystal_recrystallization_method 'Hexanes/EtOAc (column fraction)'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8730
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.858
_diffrn_reflns_theta_min         2.720
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2155
_reflns_number_total             2948
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 767 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2948
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0455
_refine_ls_restrained_S_all      0.875
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1141
_refine_ls_wR_factor_ref         0.1341
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H19C)=Sof(H19D)=Sof(H17A)=Sof(H17B)=Sof(O1A)=Sof(C18A)=Sof(H18A)=
 Sof(H18B)=1-FVAR(1)
 Sof(O1)=Sof(H15A)=Sof(H15B)=Sof(H19A)=Sof(H19B)=Sof(C18)=Sof(H20A)=Sof(H20B)=
 FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C14(H14), C1(H1)
3.b Secondary CH2 refined with riding coordinates:
 C19(H15A,H15B), C19(H19C,H19D), C17(H19A,H19B), C17(H17A,H17B), C18(H20A,
 H20B), C18A(H18A,H18B)
3.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C12(H12), C9(H9), C3(H3), C11(H11), C5(H5), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C7 C -0.9488(2) -0.7532(5) -0.6827(2) 0.0328(6) Uani 1 1 d . . . . .
C8 C -0.8457(2) -0.7579(5) -0.5893(2) 0.0318(6) Uani 1 1 d . . . . .
C10 C -0.7545(3) -0.9335(6) -0.4178(2) 0.0427(7) Uani 1 1 d . . . . .
H10 H -0.758278 -1.053511 -0.364099 0.051 Uiso 1 1 calc R . . . .
C6 C -1.0519(3) -0.9271(6) -0.6930(2) 0.0400(7) Uani 1 1 d . . . . .
H6 H -1.054365 -1.052675 -0.641166 0.048 Uiso 1 1 calc R . . . .
C2 C -0.9473(3) -0.5679(5) -0.7634(2) 0.0363(7) Uani 1 1 d . . . . .
C12 C -0.6498(3) -0.5797(6) -0.4896(2) 0.0398(7) Uani 1 1 d . . . . .
H12 H -0.583249 -0.459359 -0.483284 0.048 Uiso 1 1 calc R . . . .
C13 C -0.7420(2) -0.5792(5) -0.5800(2) 0.0322(6) Uani 1 1 d . . . . .
C9 C -0.8482(2) -0.9340(6) -0.5063(2) 0.0381(7) Uani 1 1 d . . . . .
H9 H -0.914602 -1.054461 -0.510735 0.046 Uiso 1 1 calc R . . . .
C3 C -1.0490(3) -0.5569(7) -0.8468(2) 0.0486(8) Uani 1 1 d . . . . .
H3 H -1.049164 -0.429664 -0.898304 0.058 Uiso 1 1 calc R . . . .
C11 C -0.6554(3) -0.7557(6) -0.4090(2) 0.0429(7) Uani 1 1 d . . . . .
H11 H -0.592819 -0.754379 -0.349196 0.051 Uiso 1 1 calc R . . . .
C14 C -0.7280(2) -0.3952(6) -0.6667(2) 0.0367(7) Uani 1 1 d . . . . .
H14 H -0.684467 -0.231278 -0.646196 0.044 Uiso 1 1 calc R . . . .
C5 C -1.1503(3) -0.9179(6) -0.7780(3) 0.0483(8) Uani 1 1 d . . . . .
H5 H -1.216968 -1.038031 -0.783319 0.058 Uiso 1 1 calc R . . . .
O1 O -0.6018(13) -0.942(3) -0.9616(15) 0.071(5) Uani 0.425(19) 1 d . . P A 1
C4 C -1.1497(3) -0.7315(7) -0.8545(3) 0.0529(9) Uani 1 1 d . . . . .
H4 H -1.216547 -0.722789 -0.911060 0.064 Uiso 1 1 calc R . . . .
C19 C -0.6877(3) -0.7575(8) -0.9342(2) 0.0532(9) Uani 1 1 d . . . . .
H15A H -0.772351 -0.834833 -0.936206 0.064 Uiso 0.425(19) 1 calc R . P A 1
H15B H -0.694927 -0.617369 -0.985260 0.064 Uiso 0.425(19) 1 calc R . P A 1
H19C H -0.774893 -0.824929 -0.940896 0.064 Uiso 0.575(19) 1 calc R . P A 2
H19D H -0.682442 -0.629044 -0.988787 0.064 Uiso 0.575(19) 1 calc R . P A 2
C1 C -0.8369(3) -0.3880(6) -0.7630(2) 0.0392(7) Uani 1 1 d . . . . .
H1 H -0.855379 -0.220100 -0.797508 0.047 Uiso 1 1 calc R . . . .
C16 C -0.6432(3) -0.6520(6) -0.8252(2) 0.0381(7) Uani 1 1 d . . . . .
C15 C -0.7099(2) -0.5029(6) -0.7701(2) 0.0377(7) Uani 1 1 d . . . . .
C17 C -0.5115(3) -0.7627(7) -0.7901(2) 0.0488(8) Uani 1 1 d . . . . .
H19A H -0.445321 -0.646730 -0.808047 0.059 Uiso 0.425(19) 1 calc R . P A 1
H19B H -0.497642 -0.790760 -0.714053 0.059 Uiso 0.425(19) 1 calc R . P A 1
H17A H -0.447918 -0.625707 -0.777554 0.059 Uiso 0.575(19) 1 calc R . P A 2
H17B H -0.510388 -0.860931 -0.725160 0.059 Uiso 0.575(19) 1 calc R . P A 2
C18 C -0.5086(19) -1.004(4) -0.846(2) 0.078(6) Uani 0.425(19) 1 d . . P A 1
H20A H -0.544003 -1.142995 -0.807883 0.094 Uiso 0.425(19) 1 calc R . P A 1
H20B H -0.421429 -1.048258 -0.855982 0.094 Uiso 0.425(19) 1 calc R . P A 1
O1A O -0.4846(8) -0.9264(19) -0.8739(6) 0.057(3) Uani 0.575(19) 1 d . . P A 2
C18A C -0.5911(17) -0.966(2) -0.9365(14) 0.061(4) Uani 0.575(19) 1 d . . P A 2
H18A H -0.628152 -1.128121 -0.917008 0.073 Uiso 0.575(19) 1 calc R . P A 2
H18B H -0.572305 -0.984380 -1.008348 0.073 Uiso 0.575(19) 1 calc R . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7 C8 1.486(4) . ?
C7 C6 1.397(4) . ?
C7 C2 1.408(4) . ?
C8 C13 1.419(3) . ?
C8 C9 1.400(4) . ?
C10 C9 1.382(4) . ?
C10 C11 1.379(4) . ?
C6 C5 1.384(4) . ?
C2 C3 1.392(4) . ?
C2 C1 1.485(4) . ?
C12 C13 1.391(4) . ?
C12 C11 1.380(4) . ?
C13 C14 1.483(4) . ?
C3 C4 1.382(5) . ?
C14 C1 1.550(4) . ?
C14 C15 1.470(4) . ?
C5 C4 1.372(5) . ?
O1 C19 1.393(15) . ?
O1 C18 1.68(4) . ?
C19 C16 1.502(4) . ?
C19 C18A 1.485(15) . ?
C1 C15 1.473(4) . ?
C16 C15 1.312(4) . ?
C16 C17 1.501(4) . ?
C17 C18 1.44(2) . ?
C17 O1A 1.424(8) . ?
O1A C18A 1.29(2) . ?

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
C6 C7 C8 121.7(2) . . ?
C6 C7 C2 117.4(2) . . ?
C2 C7 C8 120.8(2) . . ?
C13 C8 C7 121.0(2) . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 C13 117.4(2) . . ?
C11 C10 C9 120.3(3) . . ?
C5 C6 C7 122.0(3) . . ?
C7 C2 C1 121.1(2) . . ?
C3 C2 C7 119.8(3) . . ?
C3 C2 C1 119.1(3) . . ?
C11 C12 C13 121.2(3) . . ?
C8 C13 C14 121.0(2) . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 C14 119.1(2) . . ?
C10 C9 C8 121.7(3) . . ?
C4 C3 C2 121.3(3) . . ?
C10 C11 C12 119.5(3) . . ?
C13 C14 C1 117.7(2) . . ?
C15 C14 C13 117.8(2) . . ?
C15 C14 C1 58.30(17) . . ?
C4 C5 C6 120.0(3) . . ?
C19 O1 C18 102.9(12) . . ?
C5 C4 C3 119.5(3) . . ?
O1 C19 C16 110.9(8) . . ?
C18A C19 C16 99.4(7) . . ?
C2 C1 C14 118.0(2) . . ?
C15 C1 C2 117.3(3) . . ?
C15 C1 C14 58.14(17) . . ?
C15 C16 C19 126.3(3) . . ?
C15 C16 C17 127.1(3) . . ?
C17 C16 C19 106.5(2) . . ?
C14 C15 C1 63.56(18) . . ?
C16 C15 C14 148.5(3) . . ?
C16 C15 C1 145.8(3) . . ?
C18 C17 C16 105.6(9) . . ?
O1A C17 C16 106.1(4) . . ?
C17 C18 O1 102.6(14) . . ?
C18A O1A C17 108.1(8) . . ?
O1A C18A C19 113.7(9) . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id DT1716a
_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_dt1735_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1573403'
_audit_update_record             
;
2017-09-08 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_audit_creation_date             2017-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H22 O5'
_chemical_formula_sum            'C25 H22 O5'
_chemical_formula_weight         402.42
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5283(2)
_cell_length_b                   14.2319(3)
_cell_length_c                   14.0529(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.2910(10)
_cell_angle_gamma                90
_cell_volume                     2031.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9304
_cell_measurement_temperature    173
_cell_measurement_theta_max      26.3204
_cell_measurement_theta_min      2.4639
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24893
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.805
_diffrn.ambient_temp_esd         2.0
_diffrn_ambient_temperature      172.98
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker Photon 50'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  BrukerD8QuestEco
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker Photon 50'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens KFFMO2K--90C'
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2954
_reflns_number_total             4141
_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+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.014
_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)+(0.0513P)²+0.6734P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1024
_refine_ls_wR_factor_ref         0.1157
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(H00C)=Sof(H00D)=Sof(H00O)=Sof(H00P)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=
 Sof(O00V)=1-FVAR(1)
 Sof(H00A)=Sof(H00B)=Sof(H00E)=Sof(H00J)=Sof(C00T)=Sof(H00Y)=Sof(H)=Sof(O00U)=
 FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C00J(H00C,H00D), C00J(H00A,H00B), C00O(H00E,H00J), C00O(H00O,H00P), C00T(H00Y,
 H), C0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00M(H00M), C00N(H00N), C00P(H00Q), C00Q(H00R)
3.c Idealised Me refined as rotating group:
 C00R(H00S,H00T,H00U), C00S(H00V,H00W,H00X)
;
_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
O001 O 0.39231(12) 0.51514(8) 0.78091(10) 0.0440(3) Uani 1 1 d . . . . .
O002 O 0.18593(11) 0.55670(10) 0.70400(10) 0.0519(4) Uani 1 1 d . . . . .
O003 O 0.60193(14) 0.66028(10) 0.37220(10) 0.0553(4) Uani 1 1 d . . . . .
O004 O 0.47738(13) 0.78598(9) 0.37741(11) 0.0527(4) Uani 1 1 d . . . . .
C005 C 0.49988(15) 0.70164(11) 0.75958(12) 0.0321(4) Uani 1 1 d . . . . .
C006 C 0.35919(15) 0.59703(11) 0.63086(13) 0.0320(4) Uani 1 1 d . . . . .
C007 C 0.60467(15) 0.78306(11) 0.59729(12) 0.0325(4) Uani 1 1 d . . . . .
C008 C 0.45699(15) 0.66667(11) 0.65573(12) 0.0314(4) Uani 1 1 d . . . . .
C009 C 0.31183(15) 0.56405(11) 0.53404(13) 0.0335(4) Uani 1 1 d . . . . .
C00A C 0.30136(16) 0.55589(11) 0.70766(14) 0.0366(4) Uani 1 1 d . . . . .
C00B C 0.46809(15) 0.66407(11) 0.48630(12) 0.0332(4) Uani 1 1 d . . . . .
C00C C 0.37042(15) 0.59498(11) 0.46208(13) 0.0340(4) Uani 1 1 d . . . . .
C00D C 0.50947(15) 0.70254(11) 0.58136(13) 0.0319(4) Uani 1 1 d . . . . .
C00E C 0.52486(16) 0.70064(12) 0.40625(13) 0.0362(4) Uani 1 1 d . . . . .
C00F C 0.62830(16) 0.68849(12) 0.81650(13) 0.0364(4) Uani 1 1 d . . . . .
H00F H 0.692147 0.662326 0.787414 0.044 Uiso 1 1 calc R . . . .
C00G C 0.40912(17) 0.74265(12) 0.80339(14) 0.0395(4) Uani 1 1 d . . . . .
H00G H 0.321468 0.753394 0.765112 0.047 Uiso 1 1 calc R . . . .
C00H C 0.66374(18) 0.71320(13) 0.91504(14) 0.0439(5) Uani 1 1 d . . . . .
H00H H 0.751432 0.702958 0.953496 0.053 Uiso 1 1 calc R . . . .
C00I C 0.73543(17) 0.76879(13) 0.60064(15) 0.0457(5) Uani 1 1 d . . . . .
H00I H 0.767797 0.706591 0.599630 0.055 Uiso 1 1 calc R . . . .
C00J C 0.19646(17) 0.49666(13) 0.50572(15) 0.0427(4) Uani 1 1 d . . . . .
H00C H 0.126941 0.516328 0.537172 0.051 Uiso 0.492(7) 1 calc R . P A 2
H00D H 0.225559 0.432573 0.529024 0.051 Uiso 0.492(7) 1 calc R . P A 2
H00A H 0.202559 0.451291 0.560142 0.051 Uiso 0.508(7) 1 calc R . P A 1
H00B H 0.113595 0.532480 0.497143 0.051 Uiso 0.508(7) 1 calc R . P A 1
C00K C 0.56029(18) 0.87451(12) 0.59975(15) 0.0466(5) Uani 1 1 d . . . . .
H00K H 0.471410 0.885739 0.599931 0.056 Uiso 1 1 calc R . . . .
C00L C 0.44514(19) 0.76789(13) 0.90192(15) 0.0463(5) Uani 1 1 d . . . . .
H00L H 0.382368 0.795653 0.931011 0.056 Uiso 1 1 calc R . . . .
C00M C 0.64495(19) 0.94982(13) 0.60196(15) 0.0497(5) Uani 1 1 d . . . . .
H00M H 0.612697 1.012216 0.601330 0.060 Uiso 1 1 calc R . . . .
C00N C 0.77462(19) 0.93492(13) 0.60505(14) 0.0468(5) Uani 1 1 d . . . . .
H00N H 0.832399 0.986559 0.606885 0.056 Uiso 1 1 calc R . . . .
C00O C 0.32531(18) 0.55810(13) 0.35738(14) 0.0447(5) Uani 1 1 d . . . . .
H00E H 0.387823 0.510241 0.345796 0.054 Uiso 0.508(7) 1 calc R . P A 1
H00J H 0.320691 0.609978 0.309657 0.054 Uiso 0.508(7) 1 calc R . P A 1
H00O H 0.276495 0.608806 0.314855 0.054 Uiso 0.492(7) 1 calc R . P A 2
H00P H 0.404313 0.543858 0.334319 0.054 Uiso 0.492(7) 1 calc R . P A 2
C00P C 0.5727(2) 0.75266(13) 0.95805(15) 0.0482(5) Uani 1 1 d . . . . .
H00Q H 0.597540 0.769293 1.025914 0.058 Uiso 1 1 calc R . . . .
C00Q C 0.8200(2) 0.84427(14) 0.60545(17) 0.0551(6) Uani 1 1 d . . . . .
H00R H 0.910122 0.833311 0.609066 0.066 Uiso 1 1 calc R . . . .
C00R C 0.5392(2) 0.83207(17) 0.30940(18) 0.0683(7) Uani 1 1 d . . . . .
H00S H 0.518842 0.797418 0.246937 0.102 Uiso 1 1 calc GR . . . .
H00T H 0.634760 0.833536 0.337759 0.102 Uiso 1 1 calc GR . . . .
H00U H 0.505776 0.896455 0.297455 0.102 Uiso 1 1 calc GR . . . .
C00S C 0.3435(2) 0.47471(17) 0.85868(17) 0.0637(6) Uani 1 1 d . . . . .
H00V H 0.278228 0.426140 0.831036 0.096 Uiso 1 1 calc GR . . . .
H00W H 0.302409 0.523929 0.889248 0.096 Uiso 1 1 calc GR . . . .
H00X H 0.416779 0.446643 0.908531 0.096 Uiso 1 1 calc GR . . . .
C00T C 0.1888(7) 0.5145(5) 0.3447(4) 0.0516(14) Uani 0.508(7) 1 d . . P A 1
H00Y H 0.123940 0.564638 0.345602 0.062 Uiso 0.508(7) 1 calc R . P A 1
H H 0.161209 0.481958 0.280291 0.062 Uiso 0.508(7) 1 calc R . P A 1
O00U O 0.1919(4) 0.4491(3) 0.4224(3) 0.0513(13) Uani 0.508(7) 1 d . . P A 1
C0AA C 0.1389(5) 0.4965(5) 0.3876(4) 0.0414(13) Uani 0.492(7) 1 d . . P A 2
H0AA H 0.068682 0.448626 0.367878 0.050 Uiso 0.492(7) 1 calc R . P A 2
H0AB H 0.100540 0.558705 0.365041 0.050 Uiso 0.492(7) 1 calc R . P A 2
O00V O 0.2434(4) 0.4758(3) 0.3433(2) 0.0414(11) Uani 0.492(7) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00A 1.339(2) . ?
O001 C00S 1.444(2) . ?
O002 C00A 1.2028(19) . ?
O003 C00E 1.193(2) . ?
O004 C00E 1.335(2) . ?
O004 C00R 1.447(2) . ?
C005 C008 1.495(2) . ?
C005 C00F 1.390(2) . ?
C005 C00G 1.394(2) . ?
C006 C008 1.405(2) . ?
C006 C009 1.401(2) . ?
C006 C00A 1.492(2) . ?
C007 C00D 1.500(2) . ?
C007 C00I 1.380(2) . ?
C007 C00K 1.386(2) . ?
C008 C00D 1.401(2) . ?
C009 C00C 1.388(2) . ?
C009 C00J 1.516(2) . ?
C00B C00C 1.398(2) . ?
C00B C00D 1.402(2) . ?
C00B C00E 1.499(2) . ?
C00C C00O 1.516(3) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.381(3) . ?
C00G H00G 0.9500 . ?
C00G C00L 1.383(3) . ?
C00H H00H 0.9500 . ?
C00H C00P 1.380(3) . ?
C00I H00I 0.9500 . ?
C00I C00Q 1.385(2) . ?
C00J H00C 0.9900 . ?
C00J H00D 0.9900 . ?
C00J H00A 0.9900 . ?
C00J H00B 0.9900 . ?
C00J O00U 1.342(3) . ?
C00J C0AA 1.610(6) . ?
C00K H00K 0.9500 . ?
C00K C00M 1.389(3) . ?
C00L H00L 0.9500 . ?
C00L C00P 1.384(3) . ?
C00M H00M 0.9500 . ?
C00M C00N 1.371(3) . ?
C00N H00N 0.9500 . ?
C00N C00Q 1.375(3) . ?
C00O H00E 0.9900 . ?
C00O H00J 0.9900 . ?
C00O H00O 0.9900 . ?
C00O H00P 0.9900 . ?
C00O C00T 1.532(6) . ?
C00O O00V 1.436(3) . ?
C00P H00Q 0.9500 . ?
C00Q H00R 0.9500 . ?
C00R H00S 0.9800 . ?
C00R H00T 0.9800 . ?
C00R H00U 0.9800 . ?
C00S H00V 0.9800 . ?
C00S H00W 0.9800 . ?
C00S H00X 0.9800 . ?
C00T H00Y 0.9900 . ?
C00T H 0.9900 . ?
C00T O00U 1.428(7) . ?
C0AA H0AA 0.9900 . ?
C0AA H0AB 0.9900 . ?
C0AA O00V 1.431(6) . ?

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
C00A O001 C00S 115.42(14) . . ?
C00E O004 C00R 114.53(15) . . ?
C00F C005 C008 120.97(15) . . ?
C00F C005 C00G 118.57(16) . . ?
C00G C005 C008 120.33(14) . . ?
C008 C006 C00A 120.59(15) . . ?
C009 C006 C008 121.85(15) . . ?
C009 C006 C00A 117.55(14) . . ?
C00I C007 C00D 120.94(15) . . ?
C00I C007 C00K 118.49(16) . . ?
C00K C007 C00D 120.30(15) . . ?
C006 C008 C005 119.38(15) . . ?
C00D C008 C005 122.01(14) . . ?
C00D C008 C006 118.60(15) . . ?
C006 C009 C00J 121.49(16) . . ?
C00C C009 C006 119.25(14) . . ?
C00C C009 C00J 119.25(16) . . ?
O001 C00A C006 112.37(14) . . ?
O002 C00A O001 123.14(17) . . ?
O002 C00A C006 124.46(17) . . ?
C00C C00B C00D 122.02(16) . . ?
C00C C00B C00E 118.32(15) . . ?
C00D C00B C00E 119.60(14) . . ?
C009 C00C C00B 119.03(16) . . ?
C009 C00C C00O 120.78(15) . . ?
C00B C00C C00O 120.12(16) . . ?
C008 C00D C007 123.13(15) . . ?
C008 C00D C00B 118.93(15) . . ?
C00B C00D C007 117.90(15) . . ?
O003 C00E O004 123.80(17) . . ?
O003 C00E C00B 125.59(16) . . ?
O004 C00E C00B 110.61(15) . . ?
C005 C00F H00F 119.8 . . ?
C00H C00F C005 120.48(16) . . ?
C00H C00F H00F 119.8 . . ?
C005 C00G H00G 119.6 . . ?
C00L C00G C005 120.80(17) . . ?
C00L C00G H00G 119.6 . . ?
C00F C00H H00H 119.8 . . ?
C00P C00H C00F 120.49(17) . . ?
C00P C00H H00H 119.8 . . ?
C007 C00I H00I 119.7 . . ?
C007 C00I C00Q 120.66(17) . . ?
C00Q C00I H00I 119.7 . . ?
C009 C00J H00C 109.8 . . ?
C009 C00J H00D 109.8 . . ?
C009 C00J H00A 109.0 . . ?
C009 C00J H00B 109.0 . . ?
C009 C00J C0AA 109.2(2) . . ?
H00C C00J H00D 108.3 . . ?
H00A C00J H00B 107.8 . . ?
O00U C00J C009 112.95(19) . . ?
O00U C00J H00A 109.0 . . ?
O00U C00J H00B 109.0 . . ?
C0AA C00J H00C 109.8 . . ?
C0AA C00J H00D 109.8 . . ?
C007 C00K H00K 119.8 . . ?
C007 C00K C00M 120.43(17) . . ?
C00M C00K H00K 119.8 . . ?
C00G C00L H00L 120.0 . . ?
C00G C00L C00P 119.91(18) . . ?
C00P C00L H00L 120.0 . . ?
C00K C00M H00M 119.7 . . ?
C00N C00M C00K 120.61(17) . . ?
C00N C00M H00M 119.7 . . ?
C00M C00N H00N 120.4 . . ?
C00M C00N C00Q 119.14(17) . . ?
C00Q C00N H00N 120.4 . . ?
C00C C00O H00E 110.3 . . ?
C00C C00O H00J 110.3 . . ?
C00C C00O H00O 108.3 . . ?
C00C C00O H00P 108.3 . . ?
C00C C00O C00T 107.3(3) . . ?
H00E C00O H00J 108.5 . . ?
H00O C00O H00P 107.4 . . ?
C00T C00O H00E 110.3 . . ?
C00T C00O H00J 110.3 . . ?
O00V C00O C00C 116.1(2) . . ?
O00V C00O H00O 108.3 . . ?
O00V C00O H00P 108.3 . . ?
C00H C00P C00L 119.73(18) . . ?
C00H C00P H00Q 120.1 . . ?
C00L C00P H00Q 120.1 . . ?
C00I C00Q H00R 119.7 . . ?
C00N C00Q C00I 120.63(18) . . ?
C00N C00Q H00R 119.7 . . ?
O004 C00R H00S 109.5 . . ?
O004 C00R H00T 109.5 . . ?
O004 C00R H00U 109.5 . . ?
H00S C00R H00T 109.5 . . ?
H00S C00R H00U 109.5 . . ?
H00T C00R H00U 109.5 . . ?
O001 C00S H00V 109.5 . . ?
O001 C00S H00W 109.5 . . ?
O001 C00S H00X 109.5 . . ?
H00V C00S H00W 109.5 . . ?
H00V C00S H00X 109.5 . . ?
H00W C00S H00X 109.5 . . ?
C00O C00T H00Y 109.6 . . ?
C00O C00T H 109.6 . . ?
H00Y C00T H 108.2 . . ?
O00U C00T C00O 110.1(5) . . ?
O00U C00T H00Y 109.6 . . ?
O00U C00T H 109.6 . . ?
C00J O00U C00T 109.1(5) . . ?
C00J C0AA H0AA 109.9 . . ?
C00J C0AA H0AB 109.9 . . ?
H0AA C0AA H0AB 108.3 . . ?
O00V C0AA C00J 109.0(4) . . ?
O00V C0AA H0AA 109.9 . . ?
O00V C0AA H0AB 109.9 . . ?
C0AA O00V C00O 106.0(4) . . ?

_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_dt1723_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1561188'
_audit_update_record             
;
2017-07-10 deposited with the CCDC.
2017-09-15 downloaded from the CCDC.
;
_audit_creation_date             2017-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_publ_section_exptl              
;
Any special experimental details
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H26 O'
_chemical_formula_sum            'C33 H26 O'
_chemical_formula_weight         438.54
_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                   13.469(3)
_cell_length_b                   12.454(2)
_cell_length_c                   14.312(3)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 91.69(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     2399.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5971
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.61
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.620
_diffrn.ambient_temp_esd         2.0
_diffrn_ambient_temperature      172.99
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker Photon 50'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker Photon 50'
_diffrn_radiation_monochromator  'curved graphite'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Siemens KFFMO2K--90C'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2873
_reflns_number_total             4888
_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+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4888
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1172
_refine_ls_R_factor_gt           0.0509
_refine_ls_restrained_S_all      1.017
_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)+(0.0418P)²+0.5227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0945
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Others
 Sof(H00Y)=Sof(H)=Sof(C0AA)=Sof(H0AA)=Sof(H0AB)=1-FVAR(1)
 Sof(H00B)=Sof(H00D)=Sof(C00S)=Sof(H00S)=Sof(H00T)=FVAR(1)
 Sof(H00G)=Sof(H00M)=Sof(O00V)=1-FVAR(2)
 Sof(O00U)=Sof(H00W)=Sof(H00X)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C00M(H00B,H00D), C00M(H00G,H00M), C00S(H00S,H00T), C00W(H00W,H00X), C00W(H00Y,
 H), C0AA(H0AA,H0AB)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00C(H00C), C00E(H00E), C00F(H00F),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N),
 C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00U), C00V(H00V),
 C00X(H00Z), C00Y(H00)
;
_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
C001 C 0.24382(13) 0.65314(15) 0.27884(12) 0.0291(4) Uani 1 1 d . . . . .
C002 C 0.28725(14) 0.56354(14) 0.33673(12) 0.0299(4) Uani 1 1 d . . . . .
C003 C 0.26993(13) 0.76044(15) 0.29884(12) 0.0289(4) Uani 1 1 d . . . . .
C004 C 0.34036(13) 0.78659(14) 0.37843(13) 0.0294(4) Uani 1 1 d . . . . .
C005 C 0.22851(13) 0.84359(15) 0.24374(13) 0.0315(5) Uani 1 1 d . . . . .
C006 C 0.22649(15) 0.50156(15) 0.39203(13) 0.0365(5) Uani 1 1 d . . . . .
H006 H 0.1571 0.5154 0.3919 0.044 Uiso 1 1 calc R . . . .
C007 C 0.17725(13) 0.62991(15) 0.20445(13) 0.0324(5) Uani 1 1 d . . . . .
C008 C 0.25566(14) 0.95805(15) 0.26269(13) 0.0338(5) Uani 1 1 d . . . . .
C009 C 0.31483(14) 0.76518(15) 0.46990(13) 0.0350(5) Uani 1 1 d . . . . .
H009 H 0.2530 0.7317 0.4815 0.042 Uiso 1 1 calc R . . . .
C00A C 0.26575(16) 0.42000(16) 0.44735(14) 0.0428(5) Uani 1 1 d . . . . .
H00A H 0.2233 0.3786 0.4851 0.051 Uiso 1 1 calc R . . . .
C00B C 0.16004(14) 0.81983(16) 0.17103(13) 0.0346(5) Uani 1 1 d . . . . .
C00C C 0.31363(15) 1.01344(16) 0.20059(14) 0.0401(5) Uani 1 1 d . . . . .
H00C H 0.3353 0.9782 0.1459 0.048 Uiso 1 1 calc R . . . .
C00D C 0.15677(14) 0.51561(16) 0.17856(12) 0.0340(5) Uani 1 1 d . . . . .
C00E C 0.23029(15) 0.45364(16) 0.13981(13) 0.0390(5) Uani 1 1 d . . . . .
H00E H 0.2925 0.4854 0.1269 0.047 Uiso 1 1 calc R . . . .
C00F C 0.43125(14) 0.83543(15) 0.36357(15) 0.0389(5) Uani 1 1 d . . . . .
H00F H 0.4505 0.8503 0.3016 0.047 Uiso 1 1 calc R . . . .
C00G C 0.13461(14) 0.71348(17) 0.15113(13) 0.0356(5) Uani 1 1 d . . . . .
C00H C 0.38832(14) 0.54057(16) 0.33752(14) 0.0388(5) Uani 1 1 d . . . . .
H00H H 0.4312 0.5816 0.2999 0.047 Uiso 1 1 calc R . . . .
C00I C 0.37789(15) 0.79185(16) 0.54423(14) 0.0414(5) Uani 1 1 d . . . . .
H00I H 0.3594 0.7762 0.6063 0.050 Uiso 1 1 calc R . . . .
C00J C 0.22374(16) 1.01174(17) 0.34134(14) 0.0439(5) Uani 1 1 d . . . . .
H00J H 0.1837 0.9754 0.3848 0.053 Uiso 1 1 calc R . . . .
C00K C 0.36608(17) 0.39855(16) 0.44798(15) 0.0451(6) Uani 1 1 d . . . . .
H00K H 0.3931 0.3429 0.4863 0.054 Uiso 1 1 calc R . . . .
C00L C 0.49401(15) 0.86264(16) 0.43802(17) 0.0464(6) Uani 1 1 d . . . . .
H00L H 0.5558 0.8964 0.4269 0.056 Uiso 1 1 calc R . . . .
C00M C 0.11315(15) 0.90937(17) 0.11357(15) 0.0447(6) Uani 1 1 d . . . . .
H00B H 0.0896 0.9665 0.1556 0.054 Uiso 0.683(9) 1 calc R . P A 1
H00D H 0.1633 0.9410 0.0725 0.054 Uiso 0.683(9) 1 calc R . P A 1
H00G H 0.0789 0.9587 0.1562 0.054 Uiso 0.358(6) 1 calc R . P A 2
H00M H 0.1667 0.9505 0.0839 0.054 Uiso 0.358(6) 1 calc R . P A 2
C00N C 0.21473(17) 0.34635(17) 0.11953(15) 0.0485(6) Uani 1 1 d . . . . .
H00N H 0.2662 0.3049 0.0934 0.058 Uiso 1 1 calc R . . . .
C00O C 0.42686(16) 0.45844(17) 0.39259(15) 0.0457(5) Uani 1 1 d . . . . .
H00O H 0.4960 0.4432 0.3922 0.055 Uiso 1 1 calc R . . . .
C00P C 0.34059(16) 1.11911(17) 0.21673(16) 0.0490(6) Uani 1 1 d . . . . .
H00P H 0.3815 1.1555 0.1740 0.059 Uiso 1 1 calc R . . . .
C00Q C 0.06542(16) 0.46825(18) 0.19281(15) 0.0498(6) Uani 1 1 d . . . . .
H00Q H 0.0130 0.5100 0.2169 0.060 Uiso 1 1 calc R . . . .
C00R C 0.46725(16) 0.84102(16) 0.52858(17) 0.0465(6) Uani 1 1 d . . . . .
H00R H 0.5103 0.8600 0.5797 0.056 Uiso 1 1 calc R . . . .
C00S C 0.0286(10) 0.8676(12) 0.0559(10) 0.077(5) Uani 0.683(9) 1 d . . P A 1
H00S H -0.0263 0.8476 0.0971 0.092 Uiso 0.683(9) 1 calc R . P A 1
H00T H 0.0040 0.9247 0.0129 0.092 Uiso 0.683(9) 1 calc R . P A 1
C00T C 0.24985(18) 1.11791(18) 0.35695(16) 0.0549(6) Uani 1 1 d . . . . .
H00U H 0.2274 1.1540 0.4109 0.066 Uiso 1 1 calc R . . . .
O00U O 0.0563(2) 0.7779(2) 0.00379(17) 0.0518(12) Uani 0.642(6) 1 d . . P A 1
C00V C 0.30813(18) 1.17143(18) 0.29477(17) 0.0575(7) Uani 1 1 d . . . . .
H00V H 0.3259 1.2443 0.3057 0.069 Uiso 1 1 calc R . . . .
C00W C 0.06280(18) 0.68844(18) 0.07050(16) 0.0558(6) Uani 1 1 d . . . . .
H00W H 0.0851 0.6230 0.0380 0.067 Uiso 0.642(6) 1 calc R . P A 1
H00X H -0.0038 0.6740 0.0951 0.067 Uiso 0.642(6) 1 calc R . P A 1
H00Y H 0.0276 0.6202 0.0822 0.067 Uiso 0.317(9) 1 calc R . P A 2
H H 0.0991 0.6813 0.0117 0.067 Uiso 0.317(9) 1 calc R . P A 2
C00X C 0.12500(19) 0.29966(19) 0.13708(17) 0.0596(7) Uani 1 1 d . . . . .
H00Z H 0.1150 0.2254 0.1250 0.072 Uiso 1 1 calc R . . . .
C00Y C 0.04948(18) 0.3606(2) 0.17228(17) 0.0627(7) Uani 1 1 d . . . . .
H00 H -0.0135 0.3291 0.1825 0.075 Uiso 1 1 calc R . . . .
C0AA C -0.0128(8) 0.7832(9) 0.0628(6) 0.060(4) Uani 0.317(9) 1 d . . P A 2
H0AA H -0.0633 0.7691 0.0127 0.072 Uiso 0.317(9) 1 calc R . P A 2
H0AB H -0.0470 0.7928 0.1226 0.072 Uiso 0.317(9) 1 calc R . P A 2
O00V O 0.0433(12) 0.8753(10) 0.0419(11) 0.067(4) Uani 0.358(6) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C001 C002 1.498(3) . ?
C001 C003 1.409(2) . ?
C001 C007 1.402(3) . ?
C002 C006 1.389(3) . ?
C002 C00H 1.391(3) . ?
C003 C004 1.496(3) . ?
C003 C005 1.407(3) . ?
C004 C009 1.389(3) . ?
C004 C00F 1.389(3) . ?
C005 C008 1.494(3) . ?
C005 C00B 1.401(3) . ?
C006 H006 0.9500 . ?
C006 C00A 1.383(3) . ?
C007 C00D 1.495(3) . ?
C007 C00G 1.403(3) . ?
C008 C00C 1.384(3) . ?
C008 C00J 1.388(3) . ?
C009 H009 0.9500 . ?
C009 C00I 1.382(3) . ?
C00A H00A 0.9500 . ?
C00A C00K 1.377(3) . ?
C00B C00G 1.395(3) . ?
C00B C00M 1.513(3) . ?
C00C H00C 0.9500 . ?
C00C C00P 1.383(3) . ?
C00D C00E 1.384(3) . ?
C00D C00Q 1.385(3) . ?
C00E H00E 0.9500 . ?
C00E C00N 1.382(3) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.383(3) . ?
C00G C00W 1.516(3) . ?
C00H H00H 0.9500 . ?
C00H C00O 1.383(3) . ?
C00I H00I 0.9500 . ?
C00I C00R 1.375(3) . ?
C00J H00J 0.9500 . ?
C00J C00T 1.385(3) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.376(3) . ?
C00L H00L 0.9500 . ?
C00L C00R 1.382(3) . ?
C00M H00B 0.9900 . ?
C00M H00D 0.9900 . ?
C00M H00G 0.9900 . ?
C00M H00M 0.9900 . ?
C00M C00S 1.481(13) . ?
C00M O00V 1.436(12) . ?
C00N H00N 0.9500 . ?
C00N C00X 1.371(3) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?
C00P C00V 1.376(3) . ?
C00Q H00Q 0.9500 . ?
C00Q C00Y 1.387(3) . ?
C00R H00R 0.9500 . ?
C00S H00S 0.9900 . ?
C00S H00T 0.9900 . ?
C00S O00U 1.401(14) . ?
C00T H00U 0.9500 . ?
C00T C00V 1.376(3) . ?
O00U C00W 1.468(3) . ?
C00V H00V 0.9500 . ?
C00W H00W 0.9900 . ?
C00W H00X 0.9900 . ?
C00W H00Y 0.9900 . ?
C00W H 0.9900 . ?
C00W C0AA 1.560(9) . ?
C00X H00Z 0.9500 . ?
C00X C00Y 1.377(3) . ?
C00Y H00 0.9500 . ?
C0AA H0AA 0.9900 . ?
C0AA H0AB 0.9900 . ?
C0AA O00V 1.41(2) . ?

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
C003 C001 C002 120.19(16) . . ?
C007 C001 C002 119.79(16) . . ?
C007 C001 C003 120.02(17) . . ?
C006 C002 C001 120.12(17) . . ?
C006 C002 C00H 118.30(18) . . ?
C00H C002 C001 121.58(17) . . ?
C001 C003 C004 120.65(16) . . ?
C005 C003 C001 119.45(17) . . ?
C005 C003 C004 119.90(16) . . ?
C009 C004 C003 120.44(16) . . ?
C00F C004 C003 121.37(17) . . ?
C00F C004 C009 118.17(18) . . ?
C003 C005 C008 120.62(17) . . ?
C00B C005 C003 120.14(18) . . ?
C00B C005 C008 119.23(17) . . ?
C002 C006 H006 119.6 . . ?
C00A C006 C002 120.82(19) . . ?
C00A C006 H006 119.6 . . ?
C001 C007 C00D 119.61(17) . . ?
C001 C007 C00G 120.16(18) . . ?
C00G C007 C00D 120.13(17) . . ?
C00C C008 C005 119.90(17) . . ?
C00C C008 C00J 118.33(19) . . ?
C00J C008 C005 121.77(18) . . ?
C004 C009 H009 119.5 . . ?
C00I C009 C004 121.04(19) . . ?
C00I C009 H009 119.5 . . ?
C006 C00A H00A 119.8 . . ?
C00K C00A C006 120.3(2) . . ?
C00K C00A H00A 119.8 . . ?
C005 C00B C00M 120.20(18) . . ?
C00G C00B C005 120.28(18) . . ?
C00G C00B C00M 119.52(18) . . ?
C008 C00C H00C 119.4 . . ?
C00P C00C C008 121.15(19) . . ?
C00P C00C H00C 119.4 . . ?
C00E C00D C007 120.09(17) . . ?
C00E C00D C00Q 118.08(19) . . ?
C00Q C00D C007 121.83(18) . . ?
C00D C00E H00E 119.4 . . ?
C00N C00E C00D 121.15(19) . . ?
C00N C00E H00E 119.4 . . ?
C004 C00F H00F 119.6 . . ?
C00L C00F C004 120.73(19) . . ?
C00L C00F H00F 119.6 . . ?
C007 C00G C00W 120.20(18) . . ?
C00B C00G C007 119.92(18) . . ?
C00B C00G C00W 119.86(18) . . ?
C002 C00H H00H 119.7 . . ?
C00O C00H C002 120.50(19) . . ?
C00O C00H H00H 119.7 . . ?
C009 C00I H00I 119.9 . . ?
C00R C00I C009 120.2(2) . . ?
C00R C00I H00I 119.9 . . ?
C008 C00J H00J 119.8 . . ?
C00T C00J C008 120.5(2) . . ?
C00T C00J H00J 119.8 . . ?
C00A C00K H00K 120.3 . . ?
C00O C00K C00A 119.4(2) . . ?
C00O C00K H00K 120.3 . . ?
C00F C00L H00L 119.8 . . ?
C00R C00L C00F 120.30(19) . . ?
C00R C00L H00L 119.8 . . ?
C00B C00M H00B 109.6 . . ?
C00B C00M H00D 109.6 . . ?
C00B C00M H00G 108.5 . . ?
C00B C00M H00M 108.5 . . ?
H00B C00M H00D 108.1 . . ?
H00G C00M H00M 107.5 . . ?
C00S C00M C00B 110.3(5) . . ?
C00S C00M H00B 109.6 . . ?
C00S C00M H00D 109.6 . . ?
O00V C00M C00B 115.1(5) . . ?
O00V C00M H00G 108.5 . . ?
O00V C00M H00M 108.5 . . ?
C00E C00N H00N 120.0 . . ?
C00X C00N C00E 120.0(2) . . ?
C00X C00N H00N 120.0 . . ?
C00H C00O H00O 119.7 . . ?
C00K C00O C00H 120.6(2) . . ?
C00K C00O H00O 119.7 . . ?
C00C C00P H00P 120.1 . . ?
C00V C00P C00C 119.9(2) . . ?
C00V C00P H00P 120.1 . . ?
C00D C00Q H00Q 119.6 . . ?
C00D C00Q C00Y 120.9(2) . . ?
C00Y C00Q H00Q 119.6 . . ?
C00I C00R C00L 119.6(2) . . ?
C00I C00R H00R 120.2 . . ?
C00L C00R H00R 120.2 . . ?
C00M C00S H00S 109.4 . . ?
C00M C00S H00T 109.4 . . ?
H00S C00S H00T 108.0 . . ?
O00U C00S C00M 111.3(8) . . ?
O00U C00S H00S 109.4 . . ?
O00U C00S H00T 109.4 . . ?
C00J C00T H00U 119.8 . . ?
C00V C00T C00J 120.3(2) . . ?
C00V C00T H00U 119.8 . . ?
C00S O00U C00W 105.7(6) . . ?
C00P C00V C00T 119.8(2) . . ?
C00P C00V H00V 120.1 . . ?
C00T C00V H00V 120.1 . . ?
C00G C00W H00W 109.4 . . ?
C00G C00W H00X 109.4 . . ?
C00G C00W H00Y 110.2 . . ?
C00G C00W H 110.2 . . ?
C00G C00W C0AA 107.4(4) . . ?
O00U C00W C00G 111.3(2) . . ?
O00U C00W H00W 109.4 . . ?
O00U C00W H00X 109.4 . . ?
H00W C00W H00X 108.0 . . ?
H00Y C00W H 108.5 . . ?
C0AA C00W H00Y 110.2 . . ?
C0AA C00W H 110.2 . . ?
C00N C00X H00Z 120.1 . . ?
C00N C00X C00Y 119.9(2) . . ?
C00Y C00X H00Z 120.1 . . ?
C00Q C00Y H00 120.0 . . ?
C00X C00Y C00Q 119.9(2) . . ?
C00X C00Y H00 120.0 . . ?
C00W C0AA H0AA 110.5 . . ?
C00W C0AA H0AB 110.5 . . ?
H0AA C0AA H0AB 108.7 . . ?
O00V C0AA C00W 106.1(9) . . ?
O00V C0AA H0AA 110.5 . . ?
O00V C0AA H0AB 110.5 . . ?
C0AA O00V C00M 115.6(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
