# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd214654
_database_code_depnum_ccdc_archive 'CCDC 1033827'
_audit_update_record             
;
2014-11-12 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H18'
_chemical_formula_weight         282.36

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   22.283(3)
_cell_length_b                   10.1485(15)
_cell_length_c                   6.7864(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1534.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3545
_cell_measurement_theta_min      4.410
_cell_measurement_theta_max      54.340

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8789
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.828
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.962
_reflns_number_total             2894
_reflns_number_gt                2634
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_max     0.908
_reflns_Friedel_fraction_full    0.915

_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0673P)²+0.0452P] 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     SHELXL
_refine_ls_extinction_coef       0.041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1044 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -2.6(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2894
_refine_ls_number_parameters     200
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_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 0.42151(10) 0.4828(2) 0.2561(4) 0.0386(5) Uani 1 1 d . . . . .
C2 C 0.44620(13) 0.5783(2) 0.1314(5) 0.0540(6) Uani 1 1 d . . . . .
H2 H 0.4753 0.5537 0.0403 0.065 Uiso 1 1 calc R U . . .
C3 C 0.42847(13) 0.7067(2) 0.1409(5) 0.0594(7) Uani 1 1 d . . . . .
H3 H 0.4455 0.7683 0.0563 0.071 Uiso 1 1 calc R U . . .
C4 C 0.38532(12) 0.7463(2) 0.2755(5) 0.0551(7) Uani 1 1 d . . . . .
H4 H 0.3737 0.8342 0.2820 0.066 Uiso 1 1 calc R U . . .
C5 C 0.36001(10) 0.6558(2) 0.3982(4) 0.0476(6) Uani 1 1 d . . . . .
H5 H 0.3312 0.6826 0.4888 0.057 Uiso 1 1 calc R U . . .
C6 C 0.37693(10) 0.5221(2) 0.3896(4) 0.0398(5) Uani 1 1 d . . . . .
C7 C 0.34948(10) 0.4270(2) 0.5154(4) 0.0416(5) Uani 1 1 d . . . . .
H7 H 0.3197 0.4546 0.6021 0.050 Uiso 1 1 calc R U . . .
C8 C 0.36502(9) 0.2984(2) 0.5133(3) 0.0368(5) Uani 1 1 d . . . . .
C9 C 0.41212(9) 0.25494(19) 0.3833(4) 0.0353(5) Uani 1 1 d . . . . .
C10 C 0.44051(9) 0.3458(2) 0.2560(4) 0.0374(5) Uani 1 1 d . . . . .
C11 C 0.48816(10) 0.3004(2) 0.1385(4) 0.0461(6) Uani 1 1 d . . . . .
H11 H 0.5078 0.3593 0.0556 0.055 Uiso 1 1 calc R U . . .
C12 C 0.50625(11) 0.1725(2) 0.1430(4) 0.0501(6) Uani 1 1 d . . . . .
H12 H 0.5381 0.1454 0.0643 0.060 Uiso 1 1 calc R U . . .
C13 C 0.47764(11) 0.0822(2) 0.2638(4) 0.0493(6) Uani 1 1 d . . . . .
H13 H 0.4898 -0.0054 0.2648 0.059 Uiso 1 1 calc R U . . .
C14 C 0.43147(10) 0.1230(2) 0.3814(4) 0.0425(6) Uani 1 1 d . . . . .
H14 H 0.4124 0.0620 0.4622 0.051 Uiso 1 1 calc R U . . .
C15 C 0.33363(9) 0.2028(2) 0.6445(4) 0.0383(5) Uani 1 1 d . . . . .
C16 C 0.31793(13) 0.2415(3) 0.8507(4) 0.0531(7) Uani 1 1 d . . . . .
H16A H 0.2789 0.2157 0.9005 0.064 Uiso 1 1 calc R U . . .
H16B H 0.3322 0.3262 0.8978 0.064 Uiso 1 1 calc R U . . .
C17 C 0.36372(11) 0.1345(3) 0.8180(4) 0.0535(6) Uani 1 1 d . . . . .
H17 H 0.4062 0.1504 0.8470 0.064 Uiso 1 1 calc R U . . .
C18 C 0.33947(14) -0.0012(3) 0.8182(5) 0.0615(8) Uani 1 1 d . . . . .
H18 H 0.3514 -0.0666 0.9060 0.074 Uiso 1 1 calc R U . . .
C19 C 0.29911(13) -0.0183(2) 0.6796(5) 0.0550(7) Uani 1 1 d . . . . .
H19 H 0.2773 -0.0956 0.6622 0.066 Uiso 1 1 calc R U . . .
C20 C 0.29239(10) 0.0997(2) 0.5547(4) 0.0418(5) Uani 1 1 d . . . . .
C21 C 0.23289(11) 0.1372(3) 0.4668(5) 0.0566(7) Uani 1 1 d . . . . .
H21A H 0.1990 0.0793 0.4908 0.068 Uiso 1 1 calc R U . . .
H21B H 0.2230 0.2302 0.4597 0.068 Uiso 1 1 calc R U . . .
C22 C 0.28202(11) 0.0877(3) 0.3379(4) 0.0520(6) Uani 1 1 d . . . . .
H22A H 0.3019 0.1506 0.2524 0.062 Uiso 1 1 calc R U . . .
H22B H 0.2779 -0.0002 0.2835 0.062 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 C2 1.399(4) . ?
C1 C6 1.402(3) . ?
C1 C10 1.453(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.410(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.426(3) . ?
C7 C8 1.351(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.440(3) . ?
C8 C15 1.491(3) . ?
C9 C14 1.407(3) . ?
C9 C10 1.413(3) . ?
C10 C11 1.406(3) . ?
C11 C12 1.359(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.495(4) . ?
C15 C20 1.520(3) . ?
C15 C17 1.522(4) . ?
C16 C17 1.507(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.480(4) . ?
C17 H17 0.9800 . ?
C18 C19 1.313(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.475(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.494(4) . ?
C20 C21 1.503(4) . ?
C21 C22 1.488(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.2(2) . . ?
C2 C1 C10 123.2(2) . . ?
C6 C1 C10 118.6(2) . . ?
C3 C2 C1 121.3(3) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.3(2) . . ?
C1 C6 C7 119.87(19) . . ?
C5 C6 C7 120.8(2) . . ?
C8 C7 C6 122.5(2) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 119.27(19) . . ?
C7 C8 C15 120.16(19) . . ?
C9 C8 C15 120.57(18) . . ?
C14 C9 C10 118.6(2) . . ?
C14 C9 C8 121.3(2) . . ?
C10 C9 C8 120.06(18) . . ?
C11 C10 C9 118.08(19) . . ?
C11 C10 C1 122.3(2) . . ?
C9 C10 C1 119.6(2) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C8 C15 C16 119.8(2) . . ?
C8 C15 C20 119.5(2) . . ?
C16 C15 C20 114.5(2) . . ?
C8 C15 C17 123.47(19) . . ?
C16 C15 C17 59.90(18) . . ?
C20 C15 C17 105.27(19) . . ?
C15 C16 C17 60.92(17) . . ?
C15 C16 H16A 117.7 . . ?
C17 C16 H16A 117.7 . . ?
C15 C16 H16B 117.7 . . ?
C17 C16 H16B 117.7 . . ?
H16A C16 H16B 114.8 . . ?
C18 C17 C16 115.1(2) . . ?
C18 C17 C15 105.3(2) . . ?
C16 C17 C15 59.18(16) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C15 C17 H17 120.4 . . ?
C19 C18 C17 111.8(2) . . ?
C19 C18 H18 124.1 . . ?
C17 C18 H18 124.1 . . ?
C18 C19 C20 112.0(2) . . ?
C18 C19 H19 124.0 . . ?
C20 C19 H19 124.0 . . ?
C19 C20 C22 121.0(2) . . ?
C19 C20 C21 121.5(2) . . ?
C22 C20 C21 59.56(18) . . ?
C19 C20 C15 105.5(2) . . ?
C22 C20 C15 123.0(2) . . ?
C21 C20 C15 121.2(2) . . ?
C22 C21 C20 59.93(17) . . ?
C22 C21 H21A 117.8 . . ?
C20 C21 H21A 117.8 . . ?
C22 C21 H21B 117.8 . . ?
C20 C21 H21B 117.8 . . ?
H21A C21 H21B 114.9 . . ?
C21 C22 C20 60.51(18) . . ?
C21 C22 H22A 117.7 . . ?
C20 C22 H22A 117.7 . . ?
C21 C22 H22B 117.7 . . ?
C20 C22 H22B 117.7 . . ?
H22A C22 H22B 114.8 . . ?

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
C6 C1 C2 C3 1.2(4) . . . . ?
C10 C1 C2 C3 -177.8(2) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
C10 C1 C6 C5 177.0(2) . . . . ?
C2 C1 C6 C7 178.3(2) . . . . ?
C10 C1 C6 C7 -2.8(3) . . . . ?
C4 C5 C6 C1 1.6(4) . . . . ?
C4 C5 C6 C7 -178.7(2) . . . . ?
C1 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C8 -179.1(2) . . . . ?
C6 C7 C8 C9 1.6(3) . . . . ?
C6 C7 C8 C15 -178.4(2) . . . . ?
C7 C8 C9 C14 177.5(2) . . . . ?
C15 C8 C9 C14 -2.5(3) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C15 C8 C9 C10 178.4(2) . . . . ?
C14 C9 C10 C11 -2.1(3) . . . . ?
C8 C9 C10 C11 177.0(2) . . . . ?
C14 C9 C10 C1 -179.7(2) . . . . ?
C8 C9 C10 C1 -0.6(3) . . . . ?
C2 C1 C10 C11 4.1(4) . . . . ?
C6 C1 C10 C11 -174.8(2) . . . . ?
C2 C1 C10 C9 -178.4(2) . . . . ?
C6 C1 C10 C9 2.7(3) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C1 C10 C11 C12 178.6(2) . . . . ?
C10 C11 C12 C13 0.5(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C10 C9 C14 C13 1.6(3) . . . . ?
C8 C9 C14 C13 -177.5(2) . . . . ?
C7 C8 C15 C16 -40.1(3) . . . . ?
C9 C8 C15 C16 139.9(2) . . . . ?
C7 C8 C15 C20 110.8(2) . . . . ?
C9 C8 C15 C20 -69.2(3) . . . . ?
C7 C8 C15 C17 -111.8(3) . . . . ?
C9 C8 C15 C17 68.2(3) . . . . ?
C8 C15 C16 C17 -113.7(2) . . . . ?
C20 C15 C16 C17 94.0(2) . . . . ?
C15 C16 C17 C18 -93.4(3) . . . . ?
C8 C15 C17 C18 -141.8(2) . . . . ?
C16 C15 C17 C18 110.4(3) . . . . ?
C20 C15 C17 C18 0.6(3) . . . . ?
C8 C15 C17 C16 107.8(3) . . . . ?
C20 C15 C17 C16 -109.8(2) . . . . ?
C16 C17 C18 C19 60.0(3) . . . . ?
C15 C17 C18 C19 -2.8(3) . . . . ?
C17 C18 C19 C20 3.9(3) . . . . ?
C18 C19 C20 C22 142.4(3) . . . . ?
C18 C19 C20 C21 -146.6(3) . . . . ?
C18 C19 C20 C15 -3.3(3) . . . . ?
C8 C15 C20 C19 145.6(2) . . . . ?
C16 C15 C20 C19 -62.0(2) . . . . ?
C17 C15 C20 C19 1.4(2) . . . . ?
C8 C15 C20 C22 0.8(3) . . . . ?
C16 C15 C20 C22 153.2(2) . . . . ?
C17 C15 C20 C22 -143.4(2) . . . . ?
C8 C15 C20 C21 -70.9(3) . . . . ?
C16 C15 C20 C21 81.4(3) . . . . ?
C17 C15 C20 C21 144.9(2) . . . . ?
C19 C20 C21 C22 -109.9(3) . . . . ?
C15 C20 C21 C22 112.5(3) . . . . ?
C19 C20 C22 C21 110.8(3) . . . . ?
C15 C20 C22 C21 -109.6(3) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd214691
_database_code_depnum_ccdc_archive 'CCDC 1036129'
_audit_update_record             
;
2014-11-26 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.38

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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                   7.4014(12)
_cell_length_b                   11.2513(18)
_cell_length_c                   19.726(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.021(4)
_cell_angle_gamma                90
_cell_volume                     1642.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    899
_cell_measurement_theta_min      5.493
_cell_measurement_theta_max      39.694

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6032
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9365
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.065
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3056
_reflns_number_gt                1657
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0791P)²+0.6433P] 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         3056
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0744
_refine_ls_wR_factor_ref         0.2087
_refine_ls_wR_factor_gt          0.1758
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.053
_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 0.4846(5) 0.3143(3) 0.08232(17) 0.0543(9) Uani 1 1 d . . . . .
C2 C 0.3405(5) 0.4015(3) 0.1109(2) 0.0684(11) Uani 1 1 d . . . . .
H2A H 0.2826 0.4501 0.0762 0.082 Uiso 1 1 calc R U . . .
H2B H 0.2509 0.3625 0.1385 0.082 Uiso 1 1 calc R U . . .
C3 C 0.4846(6) 0.4683(3) 0.1526(2) 0.0770(12) Uani 1 1 d . . . . .
H3A H 0.4789 0.5541 0.1480 0.092 Uiso 1 1 calc R U . . .
H3B H 0.4922 0.4447 0.1998 0.092 Uiso 1 1 calc R U . . .
C4 C 0.6207(6) 0.4106(3) 0.1088(2) 0.0713(11) Uani 1 1 d . . . . .
C5 C 0.7695(6) 0.4348(3) 0.0789(2) 0.0680(11) Uani 1 1 d . . . . .
H5 H 0.8422 0.4977 0.0931 0.082 Uiso 1 1 calc R U . . .
C6 C 0.8208(6) 0.3592(4) 0.0211(2) 0.0853(13) Uani 1 1 d . U . . .
H6 H 0.9408 0.3564 0.0080 0.102 Uiso 1 1 calc R U . . .
C7 C 0.6979(6) 0.2955(3) -0.01230(19) 0.0669(10) Uani 1 1 d . U . . .
H7 H 0.7343 0.2493 -0.0487 0.080 Uiso 1 1 calc R U . . .
C8 C 0.5033(6) 0.2948(4) 0.0062(2) 0.0751(12) Uani 1 1 d . . . . .
H8A H 0.4493 0.2193 -0.0065 0.090 Uiso 1 1 calc R U . . .
H8B H 0.4397 0.3572 -0.0183 0.090 Uiso 1 1 calc R U . . .
C9 C 0.4970(4) 0.1976(3) 0.12122(16) 0.0473(8) Uani 1 1 d . . . . .
C10 C 0.6525(5) 0.1687(3) 0.15742(16) 0.0511(9) Uani 1 1 d . . . . .
H10 H 0.7491 0.2216 0.1574 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6695(5) 0.0641(3) 0.19366(16) 0.0546(9) Uani 1 1 d . . . . .
H11 H 0.7758 0.0488 0.2179 0.066 Uiso 1 1 calc R U . . .
C12 C 0.5300(5) -0.0184(3) 0.19446(16) 0.0530(9) Uani 1 1 d . . . . .
C13 C 0.3699(4) 0.0065(3) 0.15702(15) 0.0475(8) Uani 1 1 d . . . . .
C14 C 0.3524(4) 0.1152(3) 0.11968(15) 0.0471(8) Uani 1 1 d . . . . .
C15 C 0.1872(5) 0.1353(3) 0.08325(17) 0.0562(9) Uani 1 1 d . . . . .
H15 H 0.1722 0.2062 0.0595 0.067 Uiso 1 1 calc R U . . .
C16 C 0.0521(5) 0.0551(3) 0.08203(19) 0.0629(10) Uani 1 1 d . . . . .
H16 H -0.0531 0.0717 0.0573 0.076 Uiso 1 1 calc R U . . .
C17 C 0.0669(5) -0.0551(3) 0.11797(18) 0.0593(10) Uani 1 1 d . . . . .
C18 C 0.2268(5) -0.0769(3) 0.15588(16) 0.0533(9) Uani 1 1 d . . . . .
C19 C 0.2458(6) -0.1863(3) 0.19311(19) 0.0655(11) Uani 1 1 d . . . . .
C20 C 0.1044(8) -0.2667(4) 0.1904(2) 0.0843(14) Uani 1 1 d . . . . .
H20 H 0.1145 -0.3377 0.2143 0.101 Uiso 1 1 calc R U . . .
C21 C -0.0485(7) -0.2444(4) 0.1537(3) 0.0891(15) Uani 1 1 d . . . . .
H21 H -0.1408 -0.3005 0.1530 0.107 Uiso 1 1 calc R U . . .
C22 C -0.0705(6) -0.1399(4) 0.1172(2) 0.0785(13) Uani 1 1 d . . . . .
H22 H -0.1765 -0.1264 0.0924 0.094 Uiso 1 1 calc R U . . .
C23 C 0.5428(6) -0.1273(3) 0.23141(18) 0.0672(11) Uani 1 1 d . . . . .
H23 H 0.6476 -0.1432 0.2565 0.081 Uiso 1 1 calc R U . . .
C24 C 0.4090(7) -0.2070(3) 0.2310(2) 0.0725(12) Uani 1 1 d . . . . .
H24 H 0.4222 -0.2769 0.2558 0.087 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 C9 1.523(4) . ?
C1 C8 1.526(5) . ?
C1 C2 1.561(5) . ?
C1 C4 1.564(5) . ?
C2 C3 1.532(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.487(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.288(5) . ?
C5 C6 1.477(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.325(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.492(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.382(4) . ?
C9 C14 1.416(4) . ?
C10 C11 1.381(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.389(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.413(4) . ?
C12 C23 1.428(5) . ?
C13 C18 1.415(4) . ?
C13 C14 1.432(4) . ?
C14 C15 1.425(4) . ?
C15 C16 1.346(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.432(5) . ?
C16 H16 0.9300 . ?
C17 C22 1.394(5) . ?
C17 C18 1.410(5) . ?
C18 C19 1.439(5) . ?
C19 C20 1.383(6) . ?
C19 C24 1.429(6) . ?
C20 C21 1.356(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.336(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 C1 C8 111.5(3) . . ?
C9 C1 C2 113.3(3) . . ?
C8 C1 C2 121.3(3) . . ?
C9 C1 C4 113.3(3) . . ?
C8 C1 C4 111.1(3) . . ?
C2 C1 C4 83.3(3) . . ?
C3 C2 C1 91.6(3) . . ?
C3 C2 H2A 113.4 . . ?
C1 C2 H2A 113.4 . . ?
C3 C2 H2B 113.4 . . ?
C1 C2 H2B 113.4 . . ?
H2A C2 H2B 110.7 . . ?
C4 C3 C2 87.0(3) . . ?
C4 C3 H3A 114.2 . . ?
C2 C3 H3A 114.2 . . ?
C4 C3 H3B 114.2 . . ?
C2 C3 H3B 114.2 . . ?
H3A C3 H3B 111.3 . . ?
C5 C4 C3 140.1(4) . . ?
C5 C4 C1 123.0(4) . . ?
C3 C4 C1 93.3(3) . . ?
C4 C5 C6 117.8(4) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C7 C6 C5 120.8(4) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 122.5(4) . . ?
C6 C7 H7 118.7 . . ?
C8 C7 H7 118.7 . . ?
C7 C8 C1 110.2(3) . . ?
C7 C8 H8A 109.6 . . ?
C1 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
C1 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C10 C9 C14 118.6(3) . . ?
C10 C9 C1 120.4(3) . . ?
C14 C9 C1 121.0(3) . . ?
C11 C10 C9 122.3(3) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 118.5(3) . . ?
C11 C12 C23 122.5(4) . . ?
C13 C12 C23 119.0(3) . . ?
C12 C13 C18 119.8(3) . . ?
C12 C13 C14 120.4(3) . . ?
C18 C13 C14 119.8(3) . . ?
C9 C14 C15 123.2(3) . . ?
C9 C14 C13 119.1(3) . . ?
C15 C14 C13 117.7(3) . . ?
C16 C15 C14 122.2(3) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 121.4(4) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C22 C17 C18 119.5(4) . . ?
C22 C17 C16 122.5(4) . . ?
C18 C17 C16 118.0(3) . . ?
C17 C18 C13 121.0(3) . . ?
C17 C18 C19 119.5(3) . . ?
C13 C18 C19 119.5(4) . . ?
C20 C19 C24 123.1(4) . . ?
C20 C19 C18 118.2(4) . . ?
C24 C19 C18 118.7(4) . . ?
C21 C20 C19 121.6(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C22 121.5(4) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
C21 C22 C17 119.7(5) . . ?
C21 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C24 C23 C12 122.0(4) . . ?
C24 C23 H23 119.0 . . ?
C12 C23 H23 119.0 . . ?
C23 C24 C19 120.9(4) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C3 96.6(3) . . . . ?
C8 C1 C2 C3 -126.6(3) . . . . ?
C4 C1 C2 C3 -16.0(3) . . . . ?
C1 C2 C3 C4 16.7(3) . . . . ?
C2 C3 C4 C5 140.0(6) . . . . ?
C2 C3 C4 C1 -16.7(3) . . . . ?
C9 C1 C4 C5 101.5(4) . . . . ?
C8 C1 C4 C5 -24.9(5) . . . . ?
C2 C1 C4 C5 -146.0(4) . . . . ?
C9 C1 C4 C3 -96.1(3) . . . . ?
C8 C1 C4 C3 137.5(3) . . . . ?
C2 C1 C4 C3 16.5(3) . . . . ?
C3 C4 C5 C6 -158.4(5) . . . . ?
C1 C4 C5 C6 -6.4(6) . . . . ?
C4 C5 C6 C7 20.9(6) . . . . ?
C5 C6 C7 C8 -0.6(6) . . . . ?
C6 C7 C8 C1 -30.8(5) . . . . ?
C9 C1 C8 C7 -86.8(4) . . . . ?
C2 C1 C8 C7 135.7(3) . . . . ?
C4 C1 C8 C7 40.6(4) . . . . ?
C8 C1 C9 C10 104.4(4) . . . . ?
C2 C1 C9 C10 -114.5(3) . . . . ?
C4 C1 C9 C10 -21.8(4) . . . . ?
C8 C1 C9 C14 -73.9(4) . . . . ?
C2 C1 C9 C14 67.2(4) . . . . ?
C4 C1 C9 C14 159.9(3) . . . . ?
C14 C9 C10 C11 -1.9(5) . . . . ?
C1 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 1.0(5) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
C10 C11 C12 C23 -179.9(3) . . . . ?
C11 C12 C13 C18 178.9(3) . . . . ?
C23 C12 C13 C18 -0.9(4) . . . . ?
C11 C12 C13 C14 -0.5(4) . . . . ?
C23 C12 C13 C14 179.7(3) . . . . ?
C10 C9 C14 C15 -179.2(3) . . . . ?
C1 C9 C14 C15 -0.8(5) . . . . ?
C10 C9 C14 C13 1.7(4) . . . . ?
C1 C9 C14 C13 180.0(3) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?
C18 C13 C14 C9 -179.8(3) . . . . ?
C12 C13 C14 C15 -179.7(3) . . . . ?
C18 C13 C14 C15 0.9(4) . . . . ?
C9 C14 C15 C16 179.4(3) . . . . ?
C13 C14 C15 C16 -1.4(5) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
C15 C16 C17 C22 -179.7(3) . . . . ?
C15 C16 C17 C18 1.0(5) . . . . ?
C22 C17 C18 C13 179.2(3) . . . . ?
C16 C17 C18 C13 -1.5(5) . . . . ?
C22 C17 C18 C19 0.1(5) . . . . ?
C16 C17 C18 C19 179.5(3) . . . . ?
C12 C13 C18 C17 -178.9(3) . . . . ?
C14 C13 C18 C17 0.5(4) . . . . ?
C12 C13 C18 C19 0.2(4) . . . . ?
C14 C13 C18 C19 179.5(3) . . . . ?
C17 C18 C19 C20 -0.2(5) . . . . ?
C13 C18 C19 C20 -179.3(3) . . . . ?
C17 C18 C19 C24 179.8(3) . . . . ?
C13 C18 C19 C24 0.7(5) . . . . ?
C24 C19 C20 C21 -179.8(4) . . . . ?
C18 C19 C20 C21 0.2(6) . . . . ?
C19 C20 C21 C22 0.0(7) . . . . ?
C20 C21 C22 C17 -0.1(6) . . . . ?
C18 C17 C22 C21 0.0(5) . . . . ?
C16 C17 C22 C21 -179.3(3) . . . . ?
C11 C12 C23 C24 -179.0(3) . . . . ?
C13 C12 C23 C24 0.8(5) . . . . ?
C12 C23 C24 C19 0.1(6) . . . . ?
C20 C19 C24 C23 179.1(3) . . . . ?
C18 C19 C24 C23 -0.9(5) . . . . ?

_refine_diff_density_max         0.415
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dm15136_0m
_database_code_depnum_ccdc_archive 'CCDC 1048653'
_audit_update_record             
;
2015-02-10 deposited with the CCDC.
2016-03-04 downloaded from the CCDC.
;
_audit_creation_date             2015-02-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H18 O'
_chemical_formula_sum            'C19 H18 O'
_chemical_formula_weight         262.33
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   9.9373(12)
_cell_length_b                   5.8477(7)
_cell_length_c                   23.768(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.064(2)
_cell_angle_gamma                90
_cell_volume                     1367.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.60
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0848 before and 0.0388 after correction.
The Ratio of minimum to maximum transmission is 0.8547.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13016
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.607
_diffrn_reflns_theta_min         1.731
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3404
_reflns_number_total             4198
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+0.3753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C10(H10), C12(H12), C13(H13), C15(H15), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.85888(8) 0.52958(15) 0.92451(3) 0.02447(19) Uani 1 1 d . . . . .
C1 C 0.33769(12) 0.3161(2) 0.57291(5) 0.0238(2) Uani 1 1 d . . . . .
H1A H 0.3197 0.1509 0.5770 0.029 Uiso 1 1 calc R . . . .
H1B H 0.4363 0.3474 0.5759 0.029 Uiso 1 1 calc R . . . .
C2 C 0.25107(12) 0.4304(2) 0.52085(5) 0.0271(3) Uani 1 1 d . . . . .
H2A H 0.2110 0.3207 0.4914 0.032 Uiso 1 1 calc R . . . .
H2B H 0.2980 0.5568 0.5038 0.032 Uiso 1 1 calc R . . . .
C3 C 0.15035(12) 0.5117(2) 0.56158(5) 0.0227(2) Uani 1 1 d . . . . .
H3 H 0.0772 0.3948 0.5625 0.027 Uiso 1 1 calc R . . . .
C4 C 0.09088(12) 0.7443(2) 0.56158(5) 0.0256(2) Uani 1 1 d . . . . .
H4 H 0.0397 0.8044 0.5281 0.031 Uiso 1 1 calc R . . . .
C5 C 0.11018(12) 0.8676(2) 0.60908(5) 0.0245(2) Uani 1 1 d . . . . .
H5 H 0.0653 1.0112 0.6088 0.029 Uiso 1 1 calc R . . . .
C6 C 0.19755(11) 0.79729(19) 0.66322(5) 0.0214(2) Uani 1 1 d . . . . .
H6A H 0.1377 0.7572 0.6917 0.026 Uiso 1 1 calc R . . . .
H6B H 0.2535 0.9298 0.6781 0.026 Uiso 1 1 calc R . . . .
C7 C 0.29101(10) 0.59663(18) 0.65685(4) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.26293(11) 0.46934(19) 0.60978(5) 0.0199(2) Uani 1 1 d . . . . .
C9 C 0.40775(10) 0.55661(18) 0.70137(4) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.44303(11) 0.70827(18) 0.74579(4) 0.0178(2) Uani 1 1 d . . . . .
H10 H 0.3931 0.8464 0.7467 0.021 Uiso 1 1 calc R . . . .
C11 C 0.55120(11) 0.66382(18) 0.78989(4) 0.0174(2) Uani 1 1 d . . . . .
C12 C 0.58577(11) 0.81762(19) 0.83591(5) 0.0203(2) Uani 1 1 d . . . . .
H12 H 0.5378 0.9578 0.8367 0.024 Uiso 1 1 calc R . . . .
C13 C 0.68713(11) 0.76628(19) 0.87892(5) 0.0214(2) Uani 1 1 d . . . . .
H13 H 0.7084 0.8706 0.9095 0.026 Uiso 1 1 calc R . . . .
C14 C 0.76095(11) 0.55949(19) 0.87851(4) 0.0195(2) Uani 1 1 d . . . . .
C15 C 0.73230(10) 0.40755(19) 0.83442(4) 0.0185(2) Uani 1 1 d . . . . .
H15 H 0.7828 0.2698 0.8340 0.022 Uiso 1 1 calc R . . . .
C16 C 0.62651(10) 0.45789(18) 0.78939(4) 0.0169(2) Uani 1 1 d . . . . .
C17 C 0.59094(11) 0.30475(18) 0.74349(4) 0.0192(2) Uani 1 1 d . . . . .
H17 H 0.6411 0.1672 0.7418 0.023 Uiso 1 1 calc R . . . .
C18 C 0.48559(11) 0.35161(19) 0.70152(5) 0.0198(2) Uani 1 1 d . . . . .
H18 H 0.4637 0.2444 0.6716 0.024 Uiso 1 1 calc R . . . .
C19 C 0.94495(12) 0.3357(2) 0.92380(5) 0.0274(3) Uani 1 1 d . . . . .
H19A H 0.8902 0.1959 0.9226 0.041 Uiso 1 1 calc GR . . . .
H19B H 1.0123 0.3353 0.9581 0.041 Uiso 1 1 calc GR . . . .
H19C H 0.9917 0.3422 0.8902 0.041 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 C14 1.3690(12) . ?
O1 C19 1.4218(15) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5554(16) . ?
C1 C8 1.5182(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5609(17) . ?
C3 H3 1.0000 . ?
C3 C4 1.4831(17) . ?
C3 C8 1.5052(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3307(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.5052(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5172(15) . ?
C7 C8 1.3402(15) . ?
C7 C9 1.4751(14) . ?
C9 C10 1.3856(14) . ?
C9 C18 1.4264(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4162(14) . ?
C11 C12 1.4205(14) . ?
C11 C16 1.4187(14) . ?
C12 H12 0.9500 . ?
C12 C13 1.3642(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.4151(16) . ?
C14 C15 1.3730(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.4219(14) . ?
C16 C17 1.4173(14) . ?
C17 H17 0.9500 . ?
C17 C18 1.3686(14) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C14 O1 C19 116.99(9) . . ?
H1A C1 H1B 111.3 . . ?
C2 C1 H1A 114.2 . . ?
C2 C1 H1B 114.2 . . ?
C8 C1 H1A 114.2 . . ?
C8 C1 H1B 114.2 . . ?
C8 C1 C2 86.83(8) . . ?
C1 C2 H2A 113.9 . . ?
C1 C2 H2B 113.9 . . ?
C1 C2 C3 88.22(8) . . ?
H2A C2 H2B 111.2 . . ?
C3 C2 H2A 113.9 . . ?
C3 C2 H2B 113.9 . . ?
C2 C3 H3 109.6 . . ?
C4 C3 C2 124.71(11) . . ?
C4 C3 H3 109.6 . . ?
C4 C3 C8 113.85(9) . . ?
C8 C3 C2 87.08(8) . . ?
C8 C3 H3 109.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.16(10) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 117.5 . . ?
C4 C5 C6 125.06(11) . . ?
C6 C5 H5 117.5 . . ?
C5 C6 H6A 108.6 . . ?
C5 C6 H6B 108.6 . . ?
C5 C6 C7 114.45(9) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C8 C7 C6 117.01(9) . . ?
C8 C7 C9 124.16(10) . . ?
C9 C7 C6 118.82(9) . . ?
C3 C8 C1 91.68(8) . . ?
C7 C8 C1 138.43(10) . . ?
C7 C8 C3 126.13(10) . . ?
C10 C9 C7 122.31(10) . . ?
C10 C9 C18 117.18(9) . . ?
C18 C9 C7 120.45(9) . . ?
C9 C10 H10 119.0 . . ?
C9 C10 C11 122.08(10) . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C12 122.02(10) . . ?
C10 C11 C16 119.74(9) . . ?
C16 C11 C12 118.23(9) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.74(10) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.79(10) . . ?
C14 C13 H13 119.6 . . ?
O1 C14 C13 114.51(9) . . ?
O1 C14 C15 125.09(10) . . ?
C15 C14 C13 120.40(10) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.53(10) . . ?
C16 C15 H15 120.2 . . ?
C11 C16 C15 120.30(9) . . ?
C17 C16 C11 117.90(9) . . ?
C17 C16 C15 121.79(10) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.14(10) . . ?
C18 C17 H17 119.4 . . ?
C9 C18 H18 119.0 . . ?
C17 C18 C9 121.95(10) . . ?
C17 C18 H18 119.0 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C14 C15 C16 179.21(10) . . . . ?
C1 C2 C3 C4 135.66(11) . . . . ?
C1 C2 C3 C8 18.45(9) . . . . ?
C2 C1 C8 C3 19.00(9) . . . . ?
C2 C1 C8 C7 -138.23(15) . . . . ?
C2 C3 C4 C5 -122.43(13) . . . . ?
C2 C3 C8 C1 -18.92(9) . . . . ?
C2 C3 C8 C7 142.53(12) . . . . ?
C3 C4 C5 C6 4.67(19) . . . . ?
C4 C3 C8 C1 -145.86(10) . . . . ?
C4 C3 C8 C7 15.60(17) . . . . ?
C4 C5 C6 C7 13.65(18) . . . . ?
C5 C6 C7 C8 -16.54(15) . . . . ?
C5 C6 C7 C9 161.97(10) . . . . ?
C6 C7 C8 C1 153.74(13) . . . . ?
C6 C7 C8 C3 2.37(17) . . . . ?
C6 C7 C9 C10 -6.62(15) . . . . ?
C6 C7 C9 C18 170.43(10) . . . . ?
C7 C9 C10 C11 176.93(9) . . . . ?
C7 C9 C18 C17 -177.23(10) . . . . ?
C8 C1 C2 C3 -18.30(9) . . . . ?
C8 C3 C4 C5 -18.63(16) . . . . ?
C8 C7 C9 C10 171.78(11) . . . . ?
C8 C7 C9 C18 -11.17(16) . . . . ?
C9 C7 C8 C1 -24.7(2) . . . . ?
C9 C7 C8 C3 -176.06(10) . . . . ?
C9 C10 C11 C12 -178.90(10) . . . . ?
C9 C10 C11 C16 -0.29(16) . . . . ?
C10 C9 C18 C17 -0.03(16) . . . . ?
C10 C11 C12 C13 177.49(10) . . . . ?
C10 C11 C16 C15 -177.84(9) . . . . ?
C10 C11 C16 C17 1.00(15) . . . . ?
C11 C12 C13 C14 0.49(17) . . . . ?
C11 C16 C17 C18 -1.25(16) . . . . ?
C12 C11 C16 C15 0.84(15) . . . . ?
C12 C11 C16 C17 179.67(10) . . . . ?
C12 C13 C14 O1 -179.51(10) . . . . ?
C12 C13 C14 C15 0.51(17) . . . . ?
C13 C14 C15 C16 -0.82(16) . . . . ?
C14 C15 C16 C11 0.13(15) . . . . ?
C14 C15 C16 C17 -178.65(10) . . . . ?
C15 C16 C17 C18 177.56(10) . . . . ?
C16 C11 C12 C13 -1.15(16) . . . . ?
C16 C17 C18 C9 0.78(17) . . . . ?
C18 C9 C10 C11 -0.21(16) . . . . ?
C19 O1 C14 C13 -174.16(10) . . . . ?
C19 O1 C14 C15 5.82(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
