# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_LCAR1096b_0m
_database_code_depnum_ccdc_archive 'CCDC 1992257'
loop_
_audit_author_name
_audit_author_address
'J. Benet-Buchholz'
;Institute of Chemical Research of Catalonia (ICIQ), Spain
Spain
;
_audit_update_record             
;
2020-03-23 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        LCAR1096
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
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'

_symmetry_cell_setting           Orthorhombic
_space_group_IT_number           19
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8530(4)
_cell_length_b                   9.9104(4)
_cell_length_c                   18.1445(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1591.94(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      31.54

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.899
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            29714
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.245
_diffrn_reflns_theta_max         31.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5308
_reflns_number_gt                4865
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker APEX3 v2015.9-0'
_computing_cell_refinement       'Bruker APEX3 v2015.9-0'
_computing_data_reduction        'Bruker SAINT V8.35A'
_computing_structure_solution    'SHELXT V2014/4 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'XCIF, SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0712P)²+0.2878P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_chemical_absolute_configuration unk
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_number_reflns         5308
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1147
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.52463(17) 0.63235(16) 0.34605(9) 0.0161(3) Uani 1 1 d . . . . .
O1 O 0.54919(14) 0.68827(12) 0.28792(7) 0.0204(2) Uani 1 1 d . . . . .
C2 C 0.37610(16) 0.63566(15) 0.38839(8) 0.0143(2) Uani 1 1 d . . . . .
H2 H 0.3976 0.6826 0.4360 0.017 Uiso 1 1 calc R U . . .
O2 O 0.62935(13) 0.56703(13) 0.38472(6) 0.0196(2) Uani 1 1 d . . . . .
C3 C 0.31976(17) 0.49472(15) 0.40844(8) 0.0134(2) Uani 1 1 d . . . . .
O3 O 0.40037(15) 0.41480(12) 0.29290(6) 0.0205(2) Uani 1 1 d . . . . .
H1 H 0.4114 0.3439 0.2721 0.025 Uiso 1 1 d R U . . .
C4 C 0.32918(17) 0.39026(15) 0.35831(8) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.26715(19) 0.26131(17) 0.37291(9) 0.0188(3) Uani 1 1 d . . . . .
H5 H 0.2725 0.1921 0.3367 0.023 Uiso 1 1 calc R U . . .
C6 C 0.19940(19) 0.23679(17) 0.43939(9) 0.0199(3) Uani 1 1 d . . . . .
H6 H 0.1585 0.1500 0.4493 0.024 Uiso 1 1 calc R U . . .
C7 C 0.18950(18) 0.33911(16) 0.49360(9) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.1191(2) 0.3136(2) 0.56243(10) 0.0250(3) Uani 1 1 d . . . . .
H8 H 0.0804 0.2261 0.5726 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1060(2) 0.4128(2) 0.61430(10) 0.0282(4) Uani 1 1 d . . . . .
H9 H 0.0584 0.3944 0.6601 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1635(2) 0.5424(2) 0.59945(9) 0.0268(4) Uani 1 1 d . . . . .
H10 H 0.1547 0.6111 0.6357 0.032 Uiso 1 1 calc R U . . .
C11 C 0.23216(19) 0.57094(18) 0.53327(9) 0.0207(3) Uani 1 1 d . . . . .
H11 H 0.2694 0.6594 0.5244 0.025 Uiso 1 1 calc R U . . .
C12 C 0.24844(17) 0.47046(16) 0.47793(8) 0.0149(3) Uani 1 1 d . . . . .
C13 C 0.25372(18) 0.71769(15) 0.35010(9) 0.0169(3) Uani 1 1 d . . . . .
C14 C 0.19784(19) 0.67912(17) 0.28147(9) 0.0198(3) Uani 1 1 d . . . . .
H14 H 0.2408 0.6038 0.2568 0.024 Uiso 1 1 calc R U . . .
C15 C 0.0798(2) 0.74984(19) 0.24880(11) 0.0247(3) Uani 1 1 d . . . . .
H15 H 0.0432 0.7229 0.2018 0.030 Uiso 1 1 calc R U . . .
C16 C 0.0152(2) 0.85952(19) 0.28440(13) 0.0280(4) Uani 1 1 d . . . . .
H16 H -0.0664 0.9068 0.2623 0.034 Uiso 1 1 calc R U . . .
C17 C 0.0705(2) 0.89958(19) 0.35223(13) 0.0298(4) Uani 1 1 d . . . . .
H17 H 0.0273 0.9753 0.3765 0.036 Uiso 1 1 calc R U . . .
C18 C 0.1898(2) 0.82929(18) 0.38543(11) 0.0254(3) Uani 1 1 d . . . . .
H18 H 0.2272 0.8575 0.4320 0.031 Uiso 1 1 calc R U . . .
C19 C 0.77817(19) 0.5585(2) 0.35010(11) 0.0272(4) Uani 1 1 d . . . . .
H19A H 0.8143 0.6498 0.3367 0.033 Uiso 1 1 calc R U . . .
H19B H 0.7726 0.5032 0.3047 0.033 Uiso 1 1 calc R U . . .
C20 C 0.8839(2) 0.4949(2) 0.40439(11) 0.0312(4) Uani 1 1 d . . . . .
H20A H 0.9844 0.4864 0.3822 0.047 Uiso 1 1 calc R U . . .
H20B H 0.8462 0.4052 0.4179 0.047 Uiso 1 1 calc R U . . .
H20C H 0.8902 0.5514 0.4486 0.047 Uiso 1 1 calc R U . . .


_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
C1 O1 1.2111(19) . ?
C1 O2 1.3308(19) . ?
C1 C2 1.523(2) . ?
C2 C13 1.522(2) . ?
C2 C3 1.527(2) . ?
C2 H2 1.0000 . ?
O2 C19 1.462(2) . ?
C3 C4 1.381(2) . ?
C3 C12 1.4306(19) . ?
O3 C4 1.3656(18) . ?
O3 H1 0.8037 . ?
C4 C5 1.416(2) . ?
C5 C6 1.369(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.415(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.419(2) . ?
C7 C12 1.431(2) . ?
C8 C9 1.366(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.407(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.375(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.422(2) . ?
C11 H11 0.9500 . ?
C13 C14 1.393(2) . ?
C13 C18 1.398(2) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.401(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.498(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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
O1 C1 O2 123.83(15) . . ?
O1 C1 C2 125.76(15) . . ?
O2 C1 C2 110.24(13) . . ?
C13 C2 C1 113.30(12) . . ?
C13 C2 C3 111.39(12) . . ?
C1 C2 C3 112.48(12) . . ?
C13 C2 H2 106.4 . . ?
C1 C2 H2 106.4 . . ?
C3 C2 H2 106.4 . . ?
C1 O2 C19 115.43(13) . . ?
C4 C3 C12 118.77(13) . . ?
C4 C3 C2 120.61(12) . . ?
C12 C3 C2 120.52(13) . . ?
C4 O3 H1 108.0 . . ?
O3 C4 C3 117.83(13) . . ?
O3 C4 C5 120.15(14) . . ?
C3 C4 C5 122.02(14) . . ?
C6 C5 C4 119.67(15) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.82(15) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C8 120.76(15) . . ?
C6 C7 C12 119.41(14) . . ?
C8 C7 C12 119.82(15) . . ?
C9 C8 C7 121.04(17) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 119.61(16) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.00(17) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 121.14(16) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C3 123.34(14) . . ?
C11 C12 C7 117.38(14) . . ?
C3 C12 C7 119.27(13) . . ?
C14 C13 C18 118.89(15) . . ?
C14 C13 C2 120.94(14) . . ?
C18 C13 C2 120.09(15) . . ?
C15 C14 C13 120.62(16) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.38(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.58(17) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.44(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.08(17) . . ?
C13 C18 H18 120.0 . . ?
C17 C18 H18 120.0 . . ?
O2 C19 C20 107.74(14) . . ?
O2 C19 H19A 110.2 . . ?
C20 C19 H19A 110.2 . . ?
O2 C19 H19B 110.2 . . ?
C20 C19 H19B 110.2 . . ?
H19A C19 H19B 108.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C13 0.5(2) . . . . ?
O2 C1 C2 C13 175.79(13) . . . . ?
O1 C1 C2 C3 127.95(16) . . . . ?
O2 C1 C2 C3 -56.75(16) . . . . ?
O1 C1 O2 C19 -3.9(2) . . . . ?
C2 C1 O2 C19 -179.28(14) . . . . ?
C13 C2 C3 C4 86.92(17) . . . . ?
C1 C2 C3 C4 -41.54(18) . . . . ?
C13 C2 C3 C12 -89.48(16) . . . . ?
C1 C2 C3 C12 142.06(14) . . . . ?
C12 C3 C4 O3 -178.71(13) . . . . ?
C2 C3 C4 O3 4.8(2) . . . . ?
C12 C3 C4 C5 1.6(2) . . . . ?
C2 C3 C4 C5 -174.84(14) . . . . ?
O3 C4 C5 C6 178.35(15) . . . . ?
C3 C4 C5 C6 -2.0(2) . . . . ?
C4 C5 C6 C7 0.5(2) . . . . ?
C5 C6 C7 C8 179.91(16) . . . . ?
C5 C6 C7 C12 1.3(2) . . . . ?
C6 C7 C8 C9 -178.44(17) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C3 -179.58(16) . . . . ?
C10 C11 C12 C7 0.5(2) . . . . ?
C4 C3 C12 C11 -179.71(15) . . . . ?
C2 C3 C12 C11 -3.2(2) . . . . ?
C4 C3 C12 C7 0.2(2) . . . . ?
C2 C3 C12 C7 176.65(13) . . . . ?
C6 C7 C12 C11 178.29(15) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C6 C7 C12 C3 -1.6(2) . . . . ?
C8 C7 C12 C3 179.74(15) . . . . ?
C1 C2 C13 C14 63.34(19) . . . . ?
C3 C2 C13 C14 -64.69(18) . . . . ?
C1 C2 C13 C18 -120.18(17) . . . . ?
C3 C2 C13 C18 111.80(17) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
C2 C13 C14 C15 176.13(15) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 1.0(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C14 C13 C18 C17 0.7(3) . . . . ?
C2 C13 C18 C17 -175.90(17) . . . . ?
C16 C17 C18 C13 -0.1(3) . . . . ?
C1 O2 C19 C20 174.30(16) . . . . ?

_refine_diff_density_max         0.500
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.058
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_LCAR1185_0m
_database_code_depnum_ccdc_archive 'CCDC 1992258'
loop_
_audit_author_name
_audit_author_address
'J. Benet-Buchholz'
;Institute of Chemical Research of Catalonia (ICIQ), Spain
Spain
;
_audit_update_record             
;
2020-03-23 deposited with the CCDC.	2020-05-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        LCAR1185
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H18 O3'
_chemical_formula_weight         306.34
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'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_H-M   P2(1)/n
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   11.9062(6)
_cell_length_b                   7.6280(4)
_cell_length_c                   17.1199(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.8492(18)
_cell_angle_gamma                90
_cell_volume                     1552.92(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2866
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      32.74

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      100(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_type              'Bruker APEX DUO'
_diffrn_source_power             50
_diffrn_source_current           0.6
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 512
_diffrn_reflns_number            11833
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.134
_diffrn_reflns_theta_max         31.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5044
_reflns_number_gt                4093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3 v2015.9-0'
_computing_cell_refinement       'Bruker APEX3 v2015.9-0'
_computing_data_reduction        'Bruker SAINT V8.35A'
_computing_structure_solution    'SHELXT V2014/4 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
 SHELXle: C.B. Huebschle, G.M. Sheldrick & B. Dittrich
 J.Appl.Cryst. (2011) 44, 1281-1284.
;
_computing_publication_material  'XCIF, SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0615P)²+0.5102P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5044
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1219
_refine_ls_wR_factor_gt          0.1133
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.83277(6) 0.37385(10) 0.03923(4) 0.01528(16) Uani 1 1 d . . . . .
O2 O 0.91801(6) 0.23145(10) -0.05599(4) 0.01380(16) Uani 1 1 d . . . . .
O3 O 0.84400(7) -0.01058(12) 0.37526(4) 0.01840(17) Uani 1 1 d . . . . .
H3 H 0.7835 -0.0543 0.3893 0.028 Uiso 1 1 calc R U . . .
C18 C 0.94085(8) 0.09481(13) 0.18050(5) 0.01093(18) Uani 1 1 d . . . . .
C12 C 0.83857(8) 0.01128(14) 0.29627(6) 0.01303(19) Uani 1 1 d . . . . .
C13 C 0.93784(8) 0.07683(14) 0.26344(5) 0.01211(19) Uani 1 1 d . . . . .
C1 C 0.86543(8) 0.23804(14) 0.01100(5) 0.01112(18) Uani 1 1 d . . . . .
C9 C 0.84305(8) 0.05097(14) 0.13217(5) 0.01106(18) Uani 1 1 d . . . . .
C17 C 1.04347(8) 0.14984(14) 0.14965(6) 0.01309(19) Uani 1 1 d . . . . .
H17 H 1.0478 0.1616 0.0946 0.016 Uiso 1 1 calc R U . . .
C19 C 0.92487(9) 0.39422(15) -0.10064(6) 0.0151(2) Uani 1 1 d . . . . .
H19A H 0.9774 0.4771 -0.0734 0.018 Uiso 1 1 calc R U . . .
H19B H 0.8499 0.4503 -0.1066 0.018 Uiso 1 1 calc R U . . .
C11 C 0.74560(9) -0.02839(15) 0.24917(6) 0.0148(2) Uani 1 1 d . . . . .
H11 H 0.6792 -0.0699 0.2715 0.018 Uiso 1 1 calc R U . . .
C14 C 1.03433(9) 0.11989(15) 0.31154(6) 0.0164(2) Uani 1 1 d . . . . .
H14 H 1.0315 0.1113 0.3668 0.020 Uiso 1 1 calc R U . . .
C2 C 0.84959(8) 0.05506(14) 0.04368(5) 0.01089(18) Uani 1 1 d . . . . .
H2 H 0.9181 -0.0133 0.0313 0.013 Uiso 1 1 calc R U . . .
C16 C 1.13676(9) 0.18656(16) 0.19741(6) 0.0171(2) Uani 1 1 d . . . . .
H16 H 1.2050 0.2207 0.1752 0.021 Uiso 1 1 calc R U . . .
C10 C 0.74862(8) -0.00748(15) 0.16733(6) 0.0141(2) Uani 1 1 d . . . . .
H10 H 0.6833 -0.0347 0.1355 0.017 Uiso 1 1 calc R U . . .
C6 C 0.57240(10) -0.20449(17) -0.08183(7) 0.0209(2) Uani 1 1 d . . . . .
H6 H 0.5120 -0.2628 -0.1093 0.025 Uiso 1 1 calc R U . . .
C15 C 1.13148(9) 0.17372(17) 0.27937(6) 0.0197(2) Uani 1 1 d . . . . .
H15 H 1.1954 0.2025 0.3123 0.024 Uiso 1 1 calc R U . . .
C3 C 0.75057(8) -0.03218(14) -0.00108(5) 0.01199(19) Uani 1 1 d . . . . .
C7 C 0.65665(9) -0.30025(16) -0.04233(6) 0.0191(2) Uani 1 1 d . . . . .
H7 H 0.6535 -0.4247 -0.0423 0.023 Uiso 1 1 calc R U . . .
C8 C 0.74565(9) -0.21471(15) -0.00283(6) 0.0164(2) Uani 1 1 d . . . . .
H8 H 0.8036 -0.2813 0.0232 0.020 Uiso 1 1 calc R U . . .
C4 C 0.66512(9) 0.06290(16) -0.03992(7) 0.0184(2) Uani 1 1 d . . . . .
H4 H 0.6667 0.1874 -0.0387 0.022 Uiso 1 1 calc R U . . .
C5 C 0.57730(10) -0.02353(17) -0.08067(7) 0.0236(2) Uani 1 1 d . . . . .
H5 H 0.5202 0.0426 -0.1079 0.028 Uiso 1 1 calc R U . . .
C20 C 0.96652(11) 0.34693(17) -0.17961(7) 0.0223(2) Uani 1 1 d . . . . .
H20A H 1.0424 0.2976 -0.1731 0.033 Uiso 1 1 calc R U . . .
H20B H 0.9683 0.4523 -0.2123 0.033 Uiso 1 1 calc R U . . .
H20C H 0.9159 0.2602 -0.2048 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2152(13) . ?
O2 C1 1.3346(11) . ?
O2 C19 1.4625(13) . ?
O3 C12 1.3609(11) . ?
C18 C17 1.4185(14) . ?
C18 C13 1.4288(13) . ?
C18 C9 1.4341(13) . ?
C12 C11 1.3705(14) . ?
C12 C13 1.4245(14) . ?
C13 C14 1.4183(13) . ?
C1 C2 1.5189(14) . ?
C9 C10 1.3756(14) . ?
C9 C2 1.5211(13) . ?
C17 C16 1.3750(13) . ?
C19 C20 1.5068(15) . ?
C11 C10 1.4124(14) . ?
C14 C15 1.3685(15) . ?
C2 C3 1.5265(13) . ?
C16 C15 1.4111(15) . ?
C6 C5 1.3817(18) . ?
C6 C7 1.3891(16) . ?
C3 C4 1.3913(14) . ?
C3 C8 1.3938(16) . ?
C7 C8 1.3910(15) . ?
C4 C5 1.3937(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C19 117.26(8) . . ?
C17 C18 C13 117.59(8) . . ?
C17 C18 C9 122.95(9) . . ?
C13 C18 C9 119.42(9) . . ?
O3 C12 C11 123.69(9) . . ?
O3 C12 C13 115.83(9) . . ?
C11 C12 C13 120.47(9) . . ?
C14 C13 C12 121.08(9) . . ?
C14 C13 C18 119.68(9) . . ?
C12 C13 C18 119.22(9) . . ?
O1 C1 O2 123.15(9) . . ?
O1 C1 C2 126.08(9) . . ?
O2 C1 C2 110.73(8) . . ?
C10 C9 C18 118.75(9) . . ?
C10 C9 C2 121.73(8) . . ?
C18 C9 C2 119.31(8) . . ?
C16 C17 C18 121.61(9) . . ?
O2 C19 C20 107.17(9) . . ?
C12 C11 C10 119.94(9) . . ?
C15 C14 C13 120.81(9) . . ?
C1 C2 C9 113.52(8) . . ?
C1 C2 C3 108.82(8) . . ?
C9 C2 C3 114.49(8) . . ?
C17 C16 C15 120.17(10) . . ?
C9 C10 C11 122.17(9) . . ?
C5 C6 C7 119.31(10) . . ?
C14 C15 C16 120.09(9) . . ?
C4 C3 C8 118.78(9) . . ?
C4 C3 C2 122.74(10) . . ?
C8 C3 C2 118.48(9) . . ?
C6 C7 C8 120.28(11) . . ?
C7 C8 C3 120.61(10) . . ?
C3 C4 C5 120.35(11) . . ?
C6 C5 C4 120.65(11) . . ?

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
O3 C12 C13 C14 -1.53(15) . . . . ?
C11 C12 C13 C14 179.44(11) . . . . ?
O3 C12 C13 C18 176.78(9) . . . . ?
C11 C12 C13 C18 -2.25(16) . . . . ?
C17 C18 C13 C14 2.27(15) . . . . ?
C9 C18 C13 C14 179.96(10) . . . . ?
C17 C18 C13 C12 -176.06(10) . . . . ?
C9 C18 C13 C12 1.63(15) . . . . ?
C19 O2 C1 O1 -6.75(14) . . . . ?
C19 O2 C1 C2 171.24(8) . . . . ?
C17 C18 C9 C10 177.56(10) . . . . ?
C13 C18 C9 C10 0.00(15) . . . . ?
C17 C18 C9 C2 2.82(15) . . . . ?
C13 C18 C9 C2 -174.74(9) . . . . ?
C13 C18 C17 C16 -0.65(16) . . . . ?
C9 C18 C17 C16 -178.26(10) . . . . ?
C1 O2 C19 C20 -169.17(9) . . . . ?
O3 C12 C11 C10 -177.73(10) . . . . ?
C13 C12 C11 C10 1.22(17) . . . . ?
C12 C13 C14 C15 176.41(11) . . . . ?
C18 C13 C14 C15 -1.89(17) . . . . ?
O1 C1 C2 C9 -29.20(13) . . . . ?
O2 C1 C2 C9 152.88(8) . . . . ?
O1 C1 C2 C3 99.55(11) . . . . ?
O2 C1 C2 C3 -78.37(9) . . . . ?
C10 C9 C2 C1 118.17(11) . . . . ?
C18 C9 C2 C1 -67.25(12) . . . . ?
C10 C9 C2 C3 -7.62(14) . . . . ?
C18 C9 C2 C3 166.96(9) . . . . ?
C18 C17 C16 C15 -1.40(18) . . . . ?
C18 C9 C10 C11 -1.08(16) . . . . ?
C2 C9 C10 C11 173.53(10) . . . . ?
C12 C11 C10 C9 0.48(17) . . . . ?
C13 C14 C15 C16 -0.18(18) . . . . ?
C17 C16 C15 C14 1.83(19) . . . . ?
C1 C2 C3 C4 -23.84(12) . . . . ?
C9 C2 C3 C4 104.37(11) . . . . ?
C1 C2 C3 C8 156.33(9) . . . . ?
C9 C2 C3 C8 -75.46(12) . . . . ?
C5 C6 C7 C8 -0.75(18) . . . . ?
C6 C7 C8 C3 1.18(17) . . . . ?
C4 C3 C8 C7 -0.34(16) . . . . ?
C2 C3 C8 C7 179.50(9) . . . . ?
C8 C3 C4 C5 -0.91(16) . . . . ?
C2 C3 C4 C5 179.25(10) . . . . ?
C7 C6 C5 C4 -0.50(19) . . . . ?
C3 C4 C5 C6 1.35(19) . . . . ?

_refine_diff_density_max         0.486
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.055





#===END







