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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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#  data retrieval see:
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data_1a_structural
_audit_creation_date             2014-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r4773)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H12 O'
_chemical_formula_sum            'C20 H12 O'
_chemical_formula_weight         268.30
_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                   6.9872(2)
_cell_length_b                   22.0728(8)
_cell_length_c                   8.3974(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.838(2)
_cell_angle_gamma                90
_cell_volume                     1283.01(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    90
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9396
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -46
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            69195
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         49.791
_diffrn_reflns_theta_min         1.845
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker kappa APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker TXS'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9535
_reflns_number_total             12959
_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       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         1.061
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         12959
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0781P)²+0.0753P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1397
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C20-H20C = C20-H20A = C20-H20B
 0.98 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C1 C 0.22123(5) 0.91840(2) 0.11089(4) 0.00963(5) Uani 1 1 d . . . . .
C2 C 0.27219(5) 0.97986(2) 0.14607(4) 0.00876(5) Uani 1 1 d . . . . .
C3 C 0.32561(6) 1.00305(2) 0.30594(5) 0.01089(6) Uani 1 1 d . . . . .
H3 H 0.3236 0.9767 0.3951 0.013 Uiso 1 1 calc R . . . .
C4 C 0.37900(6) 1.06193(2) 0.33266(5) 0.01134(6) Uani 1 1 d . . . . .
H4 H 0.4137 1.0756 0.4400 0.014 Uiso 1 1 calc R . . . .
C5 C 0.38423(6) 1.10375(2) 0.20335(5) 0.01005(5) Uani 1 1 d . . . . .
C6 C 0.44896(6) 1.16363(2) 0.22932(5) 0.01305(6) Uani 1 1 d . . . . .
H6 H 0.4917 1.1772 0.3356 0.016 Uiso 1 1 calc R . . . .
C7 C 0.45100(7) 1.20321(2) 0.10065(6) 0.01445(7) Uani 1 1 d . . . . .
H7 H 0.4972 1.2434 0.1191 0.017 Uiso 1 1 calc R . . . .
C8 C 0.38545(7) 1.18398(2) -0.05520(5) 0.01323(6) Uani 1 1 d . . . . .
H8 H 0.3837 1.2117 -0.1420 0.016 Uiso 1 1 calc R . . . .
C9 C 0.32213(6) 1.12438(2) -0.08580(5) 0.01032(6) Uani 1 1 d . . . . .
C10 C 0.25849(6) 1.10347(2) -0.24589(5) 0.01214(6) Uani 1 1 d . . . . .
H10 H 0.2548 1.1309 -0.3335 0.015 Uiso 1 1 calc R . . . .
C11 C 0.20347(6) 1.04504(2) -0.27406(5) 0.01175(6) Uani 1 1 d . . . . .
H11 H 0.1612 1.0323 -0.3811 0.014 Uiso 1 1 calc R . . . .
C12 C 0.20805(5) 1.00224(2) -0.14512(4) 0.00927(5) Uani 1 1 d . . . . .
C13 C 0.15577(6) 0.94169(2) -0.17456(5) 0.01100(6) Uani 1 1 d . . . . .
H13 H 0.1154 0.9285 -0.2815 0.013 Uiso 1 1 calc R . . . .
C14 C 0.16251(6) 0.90093(2) -0.04878(5) 0.01085(6) Uani 1 1 d . . . . .
H14 H 0.1264 0.8600 -0.0712 0.013 Uiso 1 1 calc R . . . .
C15 C 0.26720(5) 1.02156(2) 0.01567(4) 0.00836(5) Uani 1 1 d . . . . .
C16 C 0.32347(5) 1.08322(2) 0.04446(4) 0.00879(5) Uani 1 1 d . . . . .
C17 C 0.23348(6) 0.87004(2) 0.23472(5) 0.01203(6) Uani 1 1 d . . . . .
C18 C 0.15322(6) 0.81137(2) 0.18341(5) 0.01343(6) Uani 1 1 d . . . . .
C19 C 0.08752(7) 0.76205(2) 0.14519(5) 0.01388(6) Uani 1 1 d . . . . .
C20 C 0.00571(8) 0.70371(2) 0.09302(7) 0.01913(8) Uani 1 1 d D . . . .
O1 O 0.30885(7) 0.87577(2) 0.37461(5) 0.02070(8) Uani 1 1 d . . . . .
H20A H 0.098(2) 0.6762(6) 0.0661(18) 0.054(4) Uiso 1 1 d D . . . .
H20B H -0.0898(18) 0.7079(6) -0.0080(14) 0.043(3) Uiso 1 1 d D . . . .
H20C H -0.0697(17) 0.6864(6) 0.1737(14) 0.042(3) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.4233(5) . ?
C1 C14 1.4017(5) . ?
C1 C17 1.4845(6) . ?
C2 C3 1.4376(5) . ?
C2 C15 1.4273(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.3624(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.4295(6) . ?
C5 C6 1.4042(6) . ?
C5 C16 1.4182(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.3911(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.3926(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.4005(6) . ?
C9 C10 1.4336(6) . ?
C9 C16 1.4209(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.3573(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.4340(5) . ?
C12 C13 1.3987(6) . ?
C12 C15 1.4224(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.3833(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.4282(5) . ?
C17 C18 1.4530(6) . ?
C17 O1 1.2266(5) . ?
C18 C19 1.2077(6) . ?
C19 C20 1.4521(7) . ?
C20 H20A 0.936(12) . ?
C20 H20B 1.009(11) . ?
C20 H20C 0.990(11) . ?

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 C17 123.44(3) . . ?
C14 C1 C2 119.54(3) . . ?
C14 C1 C17 116.98(4) . . ?
C1 C2 C3 123.98(3) . . ?
C1 C2 C15 118.43(3) . . ?
C15 C2 C3 117.58(3) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.59(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.72(3) . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 122.06(4) . . ?
C6 C5 C16 119.71(4) . . ?
C16 C5 C4 118.22(4) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 C5 120.50(4) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.12(4) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 120.92(4) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C10 121.62(4) . . ?
C8 C9 C16 119.38(4) . . ?
C16 C9 C10 118.99(4) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.91(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.18(4) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 121.17(3) . . ?
C13 C12 C15 119.29(3) . . ?
C15 C12 C11 119.54(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.37(3) . . ?
C14 C13 H13 119.8 . . ?
C1 C14 H14 119.1 . . ?
C13 C14 C1 121.77(4) . . ?
C13 C14 H14 119.1 . . ?
C2 C15 C16 120.49(3) . . ?
C12 C15 C2 120.57(3) . . ?
C12 C15 C16 118.94(3) . . ?
C5 C16 C9 119.31(4) . . ?
C5 C16 C15 120.26(3) . . ?
C9 C16 C15 120.41(3) . . ?
C18 C17 C1 116.75(4) . . ?
O1 C17 C1 124.95(4) . . ?
O1 C17 C18 118.29(4) . . ?
C19 C18 C17 178.16(5) . . ?
C18 C19 C20 177.74(5) . . ?
C19 C20 H20A 113.1(9) . . ?
C19 C20 H20B 111.1(8) . . ?
C19 C20 H20C 111.1(7) . . ?
H20A C20 H20B 104.8(12) . . ?
H20A C20 H20C 111.3(12) . . ?
H20B C20 H20C 104.9(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 177.91(4) . . . . ?
C1 C2 C15 C12 1.51(5) . . . . ?
C1 C2 C15 C16 -177.84(3) . . . . ?
C2 C1 C14 C13 1.17(6) . . . . ?
C2 C1 C17 C18 172.35(4) . . . . ?
C2 C1 C17 O1 -9.08(7) . . . . ?
C2 C3 C4 C5 0.17(6) . . . . ?
C2 C15 C16 C5 -0.27(5) . . . . ?
C2 C15 C16 C9 178.73(3) . . . . ?
C3 C2 C15 C12 -177.45(3) . . . . ?
C3 C2 C15 C16 3.20(5) . . . . ?
C3 C4 C5 C6 -176.51(4) . . . . ?
C3 C4 C5 C16 2.85(6) . . . . ?
C4 C5 C6 C7 -179.62(4) . . . . ?
C4 C5 C16 C9 178.24(4) . . . . ?
C4 C5 C16 C15 -2.76(5) . . . . ?
C5 C6 C7 C8 1.12(7) . . . . ?
C6 C5 C16 C9 -2.39(6) . . . . ?
C6 C5 C16 C15 176.62(4) . . . . ?
C6 C7 C8 C9 -1.92(7) . . . . ?
C7 C8 C9 C10 -178.51(4) . . . . ?
C7 C8 C9 C16 0.53(6) . . . . ?
C8 C9 C10 C11 177.84(4) . . . . ?
C8 C9 C16 C5 1.61(6) . . . . ?
C8 C9 C16 C15 -177.39(4) . . . . ?
C9 C10 C11 C12 -0.33(6) . . . . ?
C10 C9 C16 C5 -179.32(4) . . . . ?
C10 C9 C16 C15 1.68(6) . . . . ?
C10 C11 C12 C13 -178.45(4) . . . . ?
C10 C11 C12 C15 1.39(6) . . . . ?
C11 C12 C13 C14 179.49(4) . . . . ?
C11 C12 C15 C2 179.75(3) . . . . ?
C11 C12 C15 C16 -0.89(5) . . . . ?
C12 C13 C14 C1 -0.03(6) . . . . ?
C12 C15 C16 C5 -179.63(3) . . . . ?
C12 C15 C16 C9 -0.63(5) . . . . ?
C13 C12 C15 C2 -0.41(6) . . . . ?
C13 C12 C15 C16 178.95(3) . . . . ?
C14 C1 C2 C3 177.02(4) . . . . ?
C14 C1 C2 C15 -1.87(5) . . . . ?
C14 C1 C17 C18 -9.98(6) . . . . ?
C14 C1 C17 O1 168.59(5) . . . . ?
C15 C2 C3 C4 -3.19(6) . . . . ?
C15 C12 C13 C14 -0.35(6) . . . . ?
C16 C5 C6 C7 1.03(6) . . . . ?
C16 C9 C10 C11 -1.20(6) . . . . ?
C17 C1 C2 C3 -5.37(6) . . . . ?
C17 C1 C2 C15 175.75(4) . . . . ?
C17 C1 C14 C13 -176.60(4) . . . . ?

_olex2_computing_structure_solution_long 'SHELXS-97 (Sheldrick, 2008)'

_database_code_depnum_ccdc_archive 'CCDC 996918'
