# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_1437
_audit_creation_date             2013-04-13
_audit_creation_method           
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H22O2
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.2213(4)
_cell_length_b                   19.9582(12)
_cell_length_c                   13.3944(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.326(7)
_cell_angle_gamma                90.00
_cell_volume                     1660.32(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2594
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.6200
_cell_measurement_theta_min      3.6420
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5199
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.05
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9552
_diffrn_measured_fraction_theta_max 0.7831
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -57.00   32.00   1.0000    9.1000
omega____ theta____ kappa____ phi______ frames
    -       10.7430  -57.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -56.00   1.0000    9.1000
omega____ theta____ kappa____ phi______ frames
    -      -11.5243  178.0000 -180.0000 44
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0032881000
_diffrn_orient_matrix_UB_12      -0.0142878000
_diffrn_orient_matrix_UB_13      -0.0485253000
_diffrn_orient_matrix_UB_21      -0.0409200000
_diffrn_orient_matrix_UB_22      0.0305489000
_diffrn_orient_matrix_UB_23      -0.0204598000
_diffrn_orient_matrix_UB_31      0.1065876000
_diffrn_orient_matrix_UB_32      0.0112575000
_diffrn_orient_matrix_UB_33      -0.0060890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2580
_reflns_number_total             3152
_reflns_odcompleteness_completeness 95.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0458P)²+0.7305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1161
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H6 of C6, {H1A,H1B} of C1, H18 of C18, H20 of C20, H21 of C21, H3
  of C3, H13 of C13, {H14A,H14B} of C14, H15 of C15, H17 of C17, H8 of C8, H10
  of C10, {H11A,H11B} of C11, {H12A,H12B} of C12
 At 1.5 times of:
  {H22A,H22B,H22C} of C22
2.a Ternary CH refined with riding coordinates:
 C10(H10), C13(H13), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C11(H11A,H11B), C12(H12A,H12B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C8(H8), C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2598(3) 0.47266(10) 1.25653(14) 0.0406(5) Uani 1 1 d . . .
H1A H 1.3057 0.5074 1.3037 0.049 Uiso 1 1 calc R . .
H1B H 1.3867 0.4515 1.2319 0.049 Uiso 1 1 calc R . .
C2 C 0.9690(3) 0.40843(8) 1.23249(12) 0.0315(4) Uani 1 1 d . . .
C3 C 0.8201(3) 0.35813(9) 1.23218(12) 0.0339(4) Uani 1 1 d . . .
H3 H 0.8196 0.3272 1.2841 0.041 Uiso 1 1 calc R . .
C4 C 0.6687(3) 0.35467(8) 1.15127(12) 0.0308(4) Uani 1 1 d . . .
H4 H 0.5653 0.3210 1.1500 0.037 Uiso 1 1 calc R . .
C5 C 0.6680(3) 0.40042(8) 1.07190(12) 0.0264(4) Uani 1 1 d . . .
C6 C 0.8217(3) 0.45244(8) 1.07604(12) 0.0290(4) Uani 1 1 d . . .
H6 H 0.8228 0.4846 1.0258 0.035 Uiso 1 1 calc R . .
C7 C 0.9691(3) 0.45441(8) 1.15584(12) 0.0297(4) Uani 1 1 d . . .
C8 C 0.5181(3) 0.39845(8) 0.98302(12) 0.0272(4) Uani 1 1 d . . .
H8 H 0.5033 0.4388 0.9486 0.033 Uiso 1 1 calc R . .
C9 C 0.3997(3) 0.34820(8) 0.94370(12) 0.0258(4) Uani 1 1 d . . .
C10 C 0.3718(3) 0.27705(8) 0.97909(12) 0.0293(4) Uani 1 1 d . . .
H10 H 0.4944 0.2585 1.0193 0.035 Uiso 1 1 calc R . .
C11 C 0.1545(3) 0.27488(9) 1.02860(13) 0.0353(4) Uani 1 1 d . . .
H11A H 0.1448 0.3103 1.0778 0.042 Uiso 1 1 calc R . .
H11B H 0.1329 0.2320 1.0606 0.042 Uiso 1 1 calc R . .
C12 C -0.0110(3) 0.28562(10) 0.93853(13) 0.0369(4) Uani 1 1 d . . .
H12A H -0.1131 0.2489 0.9327 0.044 Uiso 1 1 calc R . .
H12B H -0.0891 0.3273 0.9452 0.044 Uiso 1 1 calc R . .
C13 C 0.1301(3) 0.28788(8) 0.84789(13) 0.0307(4) Uani 1 1 d . . .
H13 H 0.0546 0.2766 0.7838 0.037 Uiso 1 1 calc R . .
C14 C 0.3120(3) 0.23960(8) 0.88103(13) 0.0321(4) Uani 1 1 d . . .
H14A H 0.4279 0.2392 0.8356 0.039 Uiso 1 1 calc R . .
H14B H 0.2613 0.1944 0.8920 0.039 Uiso 1 1 calc R . .
C15 C 0.2499(3) 0.35612(8) 0.84943(12) 0.0275(4) Uani 1 1 d . . .
H15 H 0.1468 0.3922 0.8600 0.033 Uiso 1 1 calc R . .
C16 C 0.3619(3) 0.36956(8) 0.75392(12) 0.0274(4) Uani 1 1 d . . .
C17 C 0.2532(3) 0.40341(8) 0.67536(13) 0.0327(4) Uani 1 1 d . . .
H17 H 0.1160 0.4202 0.6840 0.039 Uiso 1 1 calc R . .
C18 C 0.3452(3) 0.41264(9) 0.58466(13) 0.0369(4) Uani 1 1 d . . .
H18 H 0.2678 0.4350 0.5333 0.044 Uiso 1 1 calc R . .
C19 C 0.5507(3) 0.38923(8) 0.56881(13) 0.0340(4) Uani 1 1 d . . .
C20 C 0.6603(3) 0.35589(9) 0.64731(13) 0.0337(4) Uani 1 1 d . . .
H20 H 0.7977 0.3393 0.6386 0.040 Uiso 1 1 calc R . .
C21 C 0.5692(3) 0.34682(9) 0.73812(12) 0.0313(4) Uani 1 1 d . . .
H21 H 0.6478 0.3251 0.7897 0.038 Uiso 1 1 calc R . .
C22 C 0.6526(4) 0.39960(11) 0.47065(14) 0.0483(5) Uani 1 1 d . . .
H22A H 0.6080 0.3645 0.4251 0.072 Uiso 1 1 calc R . .
H22B H 0.8065 0.3989 0.4814 0.072 Uiso 1 1 calc R . .
H22C H 0.6083 0.4421 0.4429 0.072 Uiso 1 1 calc R . .
O1 O 1.1301(2) 0.42401(7) 1.30417(9) 0.0420(3) Uani 1 1 d . . .
O2 O 1.1307(2) 0.50078(6) 1.17544(9) 0.0390(3) Uani 1 1 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 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 O1 1.436(2) . ?
C1 O2 1.428(2) . ?
C2 C3 1.366(3) . ?
C2 C7 1.377(2) . ?
C2 O1 1.383(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.396(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(2) . ?
C5 C6 1.410(2) . ?
C5 C8 1.470(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.368(2) . ?
C7 O2 1.380(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.334(2) . ?
C9 C10 1.510(2) . ?
C9 C15 1.533(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.541(2) . ?
C10 C14 1.538(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.555(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.539(2) . ?
C13 H13 0.9800 . ?
C13 C14 1.532(2) . ?
C13 C15 1.552(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15 0.9800 . ?
C15 C16 1.516(2) . ?
C16 C17 1.392(2) . ?
C16 C21 1.395(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(3) . ?
C19 C20 1.389(2) . ?
C19 C22 1.507(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.383(2) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A C1 H1B 108.5 . . ?
O1 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
O2 C1 H1A 110.2 . . ?
O2 C1 H1B 110.2 . . ?
O2 C1 O1 107.35(14) . . ?
C3 C2 C7 121.15(15) . . ?
C3 C2 O1 129.18(15) . . ?
C7 C2 O1 109.64(15) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.75(15) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 121.96(16) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 118.53(15) . . ?
C4 C5 C8 124.83(15) . . ?
C6 C5 C8 116.65(14) . . ?
C5 C6 H6 120.8 . . ?
C7 C6 C5 118.31(15) . . ?
C7 C6 H6 120.8 . . ?
C2 C7 O2 109.69(14) . . ?
C6 C7 C2 122.27(16) . . ?
C6 C7 O2 128.01(15) . . ?
C5 C8 H8 114.7 . . ?
C9 C8 C5 130.52(15) . . ?
C9 C8 H8 114.7 . . ?
C8 C9 C10 130.81(15) . . ?
C8 C9 C15 122.87(15) . . ?
C10 C9 C15 106.26(13) . . ?
C9 C10 H10 115.3 . . ?
C9 C10 C11 106.34(13) . . ?
C9 C10 C14 102.44(13) . . ?
C11 C10 H10 115.3 . . ?
C14 C10 H10 115.3 . . ?
C14 C10 C11 100.31(14) . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
C10 C11 C12 102.73(13) . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 H11A 111.2 . . ?
C12 C11 H11B 111.2 . . ?
C11 C12 H12A 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 C11 103.52(14) . . ?
C13 C12 H12A 111.1 . . ?
C13 C12 H12B 111.1 . . ?
C12 C13 H13 114.7 . . ?
C12 C13 C15 108.10(14) . . ?
C14 C13 C12 101.45(14) . . ?
C14 C13 H13 114.7 . . ?
C14 C13 C15 101.64(13) . . ?
C15 C13 H13 114.7 . . ?
C10 C14 H14A 112.8 . . ?
C10 C14 H14B 112.8 . . ?
C13 C14 C10 94.58(13) . . ?
C13 C14 H14A 112.8 . . ?
C13 C14 H14B 112.8 . . ?
H14A C14 H14B 110.3 . . ?
C9 C15 C13 100.90(13) . . ?
C9 C15 H15 109.2 . . ?
C13 C15 H15 109.2 . . ?
C16 C15 C9 115.22(13) . . ?
C16 C15 C13 112.83(13) . . ?
C16 C15 H15 109.2 . . ?
C17 C16 C15 119.80(15) . . ?
C17 C16 C21 117.13(16) . . ?
C21 C16 C15 123.01(14) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.35(17) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C19 121.34(16) . . ?
C19 C18 H18 119.3 . . ?
C18 C19 C20 117.46(16) . . ?
C18 C19 C22 121.66(17) . . ?
C20 C19 C22 120.88(18) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 C19 121.34(17) . . ?
C21 C20 H20 119.3 . . ?
C16 C21 H21 119.3 . . ?
C20 C21 C16 121.36(16) . . ?
C20 C21 H21 119.3 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C2 O1 C1 104.30(13) . . ?
C7 O2 C1 104.62(13) . . ?

_database_code_depnum_ccdc_archive 'CCDC 981812'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14Jan09a
_audit_creation_date             2014-01-21
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H24'
_chemical_formula_sum            'C25 H24'
_chemical_formula_weight         324.44
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H22O2
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 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                   6.1765(2)
_cell_length_b                   11.6169(4)
_cell_length_c                   24.6124(11)
_cell_angle_alpha                90
_cell_angle_beta                 96.136(4)
_cell_angle_gamma                90
_cell_volume                     1755.85(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3531
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.6050
_cell_measurement_theta_min      3.3320
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            9066
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.175
_diffrn_reflns_theta_min         3.051
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9984
_diffrn_measured_fraction_theta_max 0.8507
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017   77.0000  -60.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -64.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -77.0000  150.0000 107
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0257178000
_diffrn_orient_matrix_UB_12      0.0148284000
_diffrn_orient_matrix_UB_13      -0.0265244000
_diffrn_orient_matrix_UB_21      -0.0209954000
_diffrn_orient_matrix_UB_22      0.0587149000
_diffrn_orient_matrix_UB_23      0.0053587000
_diffrn_orient_matrix_UB_31      0.1106204000
_diffrn_orient_matrix_UB_32      0.0076344000
_diffrn_orient_matrix_UB_33      0.0104150000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3090
_reflns_number_total             4030
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.331
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4030
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0302P)²+1.4794P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1273
_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:
 C12(H12), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11), C20(H20),
 C21(H21), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_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
C1 C 0.7732(3) 0.44351(15) 0.23302(7) 0.0195(4) Uani 1 1 d . . . . .
C2 C 0.6058(3) 0.38192(15) 0.25143(7) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.5764 0.3066 0.2375 0.024 Uiso 1 1 calc R U . . .
C3 C 0.4747(3) 0.42729(15) 0.29068(7) 0.0196(4) Uani 1 1 d . . . . .
C4 C 0.3008(3) 0.36446(16) 0.30907(8) 0.0238(4) Uani 1 1 d . . . . .
H4 H 0.2703 0.2889 0.2956 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1761(3) 0.41126(17) 0.34605(8) 0.0270(4) Uani 1 1 d . . . . .
H5 H 0.0597 0.3680 0.3581 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2191(3) 0.52370(17) 0.36645(8) 0.0268(4) Uani 1 1 d . . . . .
H6 H 0.1306 0.5560 0.3918 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3865(3) 0.58572(17) 0.34985(8) 0.0244(4) Uani 1 1 d . . . . .
H7 H 0.4141 0.6611 0.3639 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5215(3) 0.53929(16) 0.31169(7) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.7005(3) 0.59961(16) 0.29458(7) 0.0227(4) Uani 1 1 d . . . . .
H9 H 0.7365 0.6734 0.3095 0.027 Uiso 1 1 calc R U . . .
C10 C 0.8230(3) 0.55360(15) 0.25685(7) 0.0211(4) Uani 1 1 d . . . . .
H10 H 0.9436 0.5957 0.2463 0.025 Uiso 1 1 calc R U . . .
C11 C 0.8984(3) 0.39383(15) 0.19081(7) 0.0188(4) Uani 1 1 d . . . . .
H11 H 0.9087 0.3123 0.1902 0.023 Uiso 1 1 calc R U . . .
C12 C 1.2094(3) 0.49859(15) 0.08086(7) 0.0194(4) Uani 1 1 d . . . . .
H12 H 1.2562 0.4814 0.0441 0.023 Uiso 1 1 calc R U . . .
C13 C 1.0144(3) 0.58004(15) 0.08009(7) 0.0213(4) Uani 1 1 d . . . . .
H13A H 0.8805 0.5480 0.0600 0.026 Uiso 1 1 calc R U . . .
H13B H 1.0448 0.6575 0.0660 0.026 Uiso 1 1 calc R U . . .
C14 C 1.0090(3) 0.57818(15) 0.14256(7) 0.0195(4) Uani 1 1 d . . . . .
H14 H 0.8904 0.6250 0.1564 0.023 Uiso 1 1 calc R U . . .
C15 C 0.9983(3) 0.44993(14) 0.15350(7) 0.0172(4) Uani 1 1 d . . . . .
C16 C 1.1271(3) 0.39207(14) 0.11110(7) 0.0165(3) Uani 1 1 d . . . . .
H16 H 1.2548 0.3505 0.1304 0.020 Uiso 1 1 calc R U . . .
C17 C 1.2439(3) 0.61803(16) 0.16225(8) 0.0231(4) Uani 1 1 d . . . . .
H17A H 1.2903 0.5902 0.1997 0.028 Uiso 1 1 calc R U . . .
H17B H 1.2559 0.7030 0.1615 0.028 Uiso 1 1 calc R U . . .
C18 C 1.3809(3) 0.56160(16) 0.12002(8) 0.0224(4) Uani 1 1 d . . . . .
H18A H 1.4583 0.6206 0.1004 0.027 Uiso 1 1 calc R U . . .
H18B H 1.4887 0.5069 0.1380 0.027 Uiso 1 1 calc R U . . .
C19 C 1.0002(3) 0.31037(14) 0.07166(7) 0.0172(4) Uani 1 1 d . . . . .
C20 C 1.1121(3) 0.22350(15) 0.04714(7) 0.0186(4) Uani 1 1 d . . . . .
H20 H 1.2620 0.2114 0.0588 0.022 Uiso 1 1 calc R U . . .
C21 C 1.0093(3) 0.15421(15) 0.00603(7) 0.0200(4) Uani 1 1 d . . . . .
H21 H 1.0905 0.0967 -0.0103 0.024 Uiso 1 1 calc R U . . .
C22 C 0.7893(3) 0.16808(15) -0.01144(7) 0.0213(4) Uani 1 1 d . . . . .
C23 C 0.6767(3) 0.25273(16) 0.01391(8) 0.0218(4) Uani 1 1 d . . . . .
H23 H 0.5259 0.2635 0.0028 0.026 Uiso 1 1 calc R U . . .
C24 C 0.7780(3) 0.32184(16) 0.05489(7) 0.0204(4) Uani 1 1 d . . . . .
H24 H 0.6953 0.3778 0.0718 0.024 Uiso 1 1 calc R U . . .
C25 C 0.6767(3) 0.09560(17) -0.05670(8) 0.0297(5) Uani 1 1 d . . . . .
H25A H 0.5749 0.0428 -0.0416 0.045 Uiso 1 1 calc R U . . .
H25B H 0.7854 0.0512 -0.0741 0.045 Uiso 1 1 calc R U . . .
H25C H 0.5966 0.1456 -0.0839 0.045 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 1.373(2) . ?
C1 C10 1.427(2) . ?
C1 C11 1.477(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.426(2) . ?
C3 C4 1.412(2) . ?
C3 C8 1.418(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.359(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.427(2) . ?
C8 C9 1.411(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.368(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C15 1.330(2) . ?
C12 H12 1.0000 . ?
C12 C13 1.530(2) . ?
C12 C16 1.557(2) . ?
C12 C18 1.539(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.542(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.517(2) . ?
C14 C17 1.551(2) . ?
C15 C16 1.533(2) . ?
C16 H16 1.0000 . ?
C16 C19 1.515(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.554(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.396(2) . ?
C19 C24 1.397(2) . ?
C20 H20 0.9500 . ?
C20 C21 1.392(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.390(3) . ?
C22 C23 1.390(3) . ?
C22 C25 1.506(3) . ?
C23 H23 0.9500 . ?
C23 C24 1.385(3) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C2 C1 C10 117.92(16) . . ?
C2 C1 C11 119.84(16) . . ?
C10 C1 C11 122.23(16) . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.20(17) . . ?
C3 C2 H2 118.9 . . ?
C4 C3 C2 122.17(17) . . ?
C4 C3 C8 119.29(16) . . ?
C8 C3 C2 118.54(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.67(18) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.39(18) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.20(17) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.5 . . ?
C6 C7 C8 120.97(18) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 C7 118.45(17) . . ?
C9 C8 C3 118.84(16) . . ?
C9 C8 C7 122.71(17) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.11(17) . . ?
C10 C9 H9 119.4 . . ?
C1 C10 H10 119.4 . . ?
C9 C10 C1 121.24(17) . . ?
C9 C10 H10 119.4 . . ?
C1 C11 H11 116.2 . . ?
C15 C11 C1 127.62(16) . . ?
C15 C11 H11 116.2 . . ?
C13 C12 H12 114.6 . . ?
C13 C12 C16 101.57(13) . . ?
C13 C12 C18 101.65(14) . . ?
C16 C12 H12 114.6 . . ?
C18 C12 H12 114.6 . . ?
C18 C12 C16 108.45(14) . . ?
C12 C13 H13A 112.8 . . ?
C12 C13 H13B 112.8 . . ?
C12 C13 C14 94.58(14) . . ?
H13A C13 H13B 110.3 . . ?
C14 C13 H13A 112.8 . . ?
C14 C13 H13B 112.8 . . ?
C13 C14 H14 115.2 . . ?
C13 C14 C17 100.85(14) . . ?
C15 C14 C13 101.35(14) . . ?
C15 C14 H14 115.2 . . ?
C15 C14 C17 107.14(14) . . ?
C17 C14 H14 115.2 . . ?
C11 C15 C14 129.48(16) . . ?
C11 C15 C16 124.59(15) . . ?
C14 C15 C16 105.92(14) . . ?
C12 C16 H16 109.2 . . ?
C15 C16 C12 101.34(13) . . ?
C15 C16 H16 109.2 . . ?
C19 C16 C12 111.38(14) . . ?
C19 C16 C15 116.13(14) . . ?
C19 C16 H16 109.2 . . ?
C14 C17 H17A 111.2 . . ?
C14 C17 H17B 111.2 . . ?
C14 C17 C18 102.90(14) . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C12 C18 C17 103.41(14) . . ?
C12 C18 H18A 111.1 . . ?
C12 C18 H18B 111.1 . . ?
C17 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
H18A C18 H18B 109.0 . . ?
C20 C19 C16 118.94(15) . . ?
C20 C19 C24 117.21(16) . . ?
C24 C19 C16 123.66(15) . . ?
C19 C20 H20 119.2 . . ?
C21 C20 C19 121.59(17) . . ?
C21 C20 H20 119.2 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.85(17) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C25 121.51(17) . . ?
C23 C22 C21 117.55(17) . . ?
C23 C22 C25 120.93(17) . . ?
C22 C23 H23 119.1 . . ?
C24 C23 C22 121.87(17) . . ?
C24 C23 H23 119.1 . . ?
C19 C24 H24 119.6 . . ?
C23 C24 C19 120.88(17) . . ?
C23 C24 H24 119.6 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_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.
;
_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 984185'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_exp_2826
_audit_creation_date             2014-01-21
_audit_creation_method           
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 O2'
_chemical_formula_sum            'C22 H22 O2'
_chemical_formula_weight         318.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   19.1645(14)
_cell_length_b                   5.9934(5)
_cell_length_c                   29.725(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.230(8)
_cell_angle_gamma                90
_cell_volume                     3379.1(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      28.7290
_cell_measurement_theta_min      3.7340
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.1238
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            7934
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.288
_diffrn_reflns_theta_min         3.253
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9850
_diffrn_measured_fraction_theta_max 0.8343
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   17.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -19.0000  -30.0000 66

#__ type_ start__ end____ width___ exp.time_
  2 omega   36.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579 -178.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   27.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -99.0000 -120.0000 38

#__ type_ start__ end____ width___ exp.time_
  4 omega  -74.00  -21.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7173  -38.0000 -120.0000 53
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0092347000
_diffrn_orient_matrix_UB_12      0.1145843000
_diffrn_orient_matrix_UB_13      0.0001506000
_diffrn_orient_matrix_UB_21      0.0159335000
_diffrn_orient_matrix_UB_22      -0.0162302000
_diffrn_orient_matrix_UB_23      -0.0198812000
_diffrn_orient_matrix_UB_31      -0.0325367000
_diffrn_orient_matrix_UB_32      0.0247400000
_diffrn_orient_matrix_UB_33      -0.0136474000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2365
_reflns_number_total             3855
_reflns_odcompleteness_completeness 98.50
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1203
_refine_ls_R_factor_gt           0.0711
_refine_ls_restrained_S_all      1.055
_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)+(0.0540P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1779
_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:
 C1(H1), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13), C16(H16), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.49089(11) 0.6638(5) 0.85461(8) 0.0184(6) Uani 1 1 d . . . . .
H1 H 0.5052 0.7969 0.8378 0.022 Uiso 1 1 calc R U . . .
C2 C 0.50407(12) 0.4360(5) 0.83321(9) 0.0249(6) Uani 1 1 d . . . . .
H2A H 0.5499 0.4341 0.8215 0.030 Uiso 1 1 calc R U . . .
H2B H 0.4660 0.3991 0.8082 0.030 Uiso 1 1 calc R U . . .
C3 C 0.50429(12) 0.2718(5) 0.87368(9) 0.0234(6) Uani 1 1 d . . . . .
H3A H 0.4664 0.1592 0.8671 0.028 Uiso 1 1 calc R U . . .
H3B H 0.5502 0.1942 0.8804 0.028 Uiso 1 1 calc R U . . .
C4 C 0.49144(11) 0.4220(4) 0.91291(9) 0.0194(6) Uani 1 1 d . . . . .
H4 H 0.5060 0.3568 0.9438 0.023 Uiso 1 1 calc R U . . .
C5 C 0.41306(11) 0.5015(4) 0.90346(8) 0.0177(6) Uani 1 1 d . . . . .
H5 H 0.3831 0.3720 0.8915 0.021 Uiso 1 1 calc R U . . .
C6 C 0.41561(11) 0.6670(4) 0.86485(8) 0.0175(6) Uani 1 1 d . . . . .
C7 C 0.53099(11) 0.6328(4) 0.90313(8) 0.0217(6) Uani 1 1 d . . . . .
H7A H 0.5821 0.6069 0.9035 0.026 Uiso 1 1 calc R U . . .
H7B H 0.5233 0.7576 0.9237 0.026 Uiso 1 1 calc R U . . .
C8 C 0.38595(11) 0.5885(4) 0.94524(8) 0.0168(6) Uani 1 1 d . . . . .
C9 C 0.34819(11) 0.4434(4) 0.97004(8) 0.0193(6) Uani 1 1 d . . . . .
H9 H 0.3383 0.2963 0.9591 0.023 Uiso 1 1 calc R U . . .
C10 C 0.32509(11) 0.5089(4) 1.00990(8) 0.0190(6) Uani 1 1 d . . . . .
H10 H 0.2997 0.4071 1.0260 0.023 Uiso 1 1 calc R U . . .
C11 C 0.33881(11) 0.7227(4) 1.02655(8) 0.0180(6) Uani 1 1 d . . . . .
C12 C 0.37539(11) 0.8711(4) 1.00202(8) 0.0191(6) Uani 1 1 d . . . . .
H12 H 0.3846 1.0188 1.0129 0.023 Uiso 1 1 calc R U . . .
C13 C 0.39830(11) 0.8040(4) 0.96204(8) 0.0185(6) Uani 1 1 d . . . . .
H13 H 0.4229 0.9069 0.9457 0.022 Uiso 1 1 calc R U . . .
C14 C 0.31385(11) 0.7895(5) 1.06932(9) 0.0198(6) Uani 1 1 d . . . . .
C15 C 0.29896(13) 1.0870(5) 1.11929(8) 0.0255(6) Uani 1 1 d . . . . .
H15A H 0.2494 1.0467 1.1193 0.038 Uiso 1 1 calc R U . . .
H15B H 0.3040 1.2496 1.1212 0.038 Uiso 1 1 calc R U . . .
H15C H 0.3278 1.0180 1.1455 0.038 Uiso 1 1 calc R U . . .
C16 C 0.36074(11) 0.7867(4) 0.84571(8) 0.0166(5) Uani 1 1 d . . . . .
H16 H 0.3184 0.7675 0.8584 0.020 Uiso 1 1 calc R U . . .
C17 C 0.35698(11) 0.9446(4) 0.80765(8) 0.0169(6) Uani 1 1 d . . . . .
C18 C 0.39604(12) 0.9214(5) 0.77168(8) 0.0221(6) Uani 1 1 d . . . . .
H18 H 0.4267 0.7974 0.7709 0.026 Uiso 1 1 calc R U . . .
C19 C 0.39036(12) 1.0787(5) 0.73702(9) 0.0260(7) Uani 1 1 d . . . . .
H19 H 0.4179 1.0623 0.7131 0.031 Uiso 1 1 calc R U . . .
C20 C 0.34516(12) 1.2588(5) 0.73688(9) 0.0251(6) Uani 1 1 d . . . . .
H20 H 0.3415 1.3654 0.7130 0.030 Uiso 1 1 calc R U . . .
C21 C 0.30524(12) 1.2817(5) 0.77215(8) 0.0236(6) Uani 1 1 d . . . . .
H21 H 0.2740 1.4045 0.7725 0.028 Uiso 1 1 calc R U . . .
C22 C 0.31104(11) 1.1260(4) 0.80666(8) 0.0192(6) Uani 1 1 d . . . . .
H22 H 0.2831 1.1426 0.8304 0.023 Uiso 1 1 calc R U . . .
O1 O 0.28964(9) 0.6619(3) 1.09486(6) 0.0283(5) Uani 1 1 d . . . . .
O2 O 0.32203(8) 1.0084(3) 1.07781(5) 0.0215(4) Uani 1 1 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 H1 1.0000 . ?
C1 C2 1.542(4) . ?
C1 C6 1.517(3) . ?
C1 C7 1.545(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.554(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(4) . ?
C4 H4 1.0000 . ?
C4 C5 1.563(3) . ?
C4 C7 1.523(4) . ?
C5 H5 1.0000 . ?
C5 C6 1.523(3) . ?
C5 C8 1.506(3) . ?
C6 C16 1.332(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.406(3) . ?
C8 C13 1.393(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.385(4) . ?
C11 C12 1.400(3) . ?
C11 C14 1.476(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9500 . ?
C14 O1 1.216(3) . ?
C14 O2 1.341(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 O2 1.447(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.469(3) . ?
C17 C18 1.397(3) . ?
C17 C22 1.397(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.384(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.390(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(4) . ?
C22 H22 0.9500 . ?

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 H1 115.3 . . ?
C2 C1 C7 100.9(2) . . ?
C6 C1 H1 115.3 . . ?
C6 C1 C2 108.1(2) . . ?
C6 C1 C7 100.05(18) . . ?
C7 C1 H1 115.3 . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C1 C2 C3 103.0(2) . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 C2 103.6(2) . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
C3 C4 H4 114.7 . . ?
C3 C4 C5 107.44(18) . . ?
C3 C4 C7 101.8(2) . . ?
C5 C4 H4 114.7 . . ?
C7 C4 H4 114.7 . . ?
C7 C4 C5 101.8(2) . . ?
C4 C5 H5 108.4 . . ?
C6 C5 C4 101.55(18) . . ?
C6 C5 H5 108.4 . . ?
C8 C5 C4 113.18(18) . . ?
C8 C5 H5 108.4 . . ?
C8 C5 C6 116.6(2) . . ?
C1 C6 C5 106.09(19) . . ?
C16 C6 C1 129.5(2) . . ?
C16 C6 C5 124.4(2) . . ?
C1 C7 H7A 112.8 . . ?
C1 C7 H7B 112.8 . . ?
C4 C7 C1 94.80(18) . . ?
C4 C7 H7A 112.8 . . ?
C4 C7 H7B 112.8 . . ?
H7A C7 H7B 110.2 . . ?
C9 C8 C5 118.8(2) . . ?
C13 C8 C5 123.8(2) . . ?
C13 C8 C9 117.3(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 C8 121.8(2) . . ?
C10 C9 H9 119.1 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.1(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 119.0(2) . . ?
C10 C11 C14 119.4(2) . . ?
C12 C11 C14 121.6(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.4 . . ?
C12 C13 C8 121.2(2) . . ?
C12 C13 H13 119.4 . . ?
O1 C14 C11 124.5(3) . . ?
O1 C14 O2 122.9(2) . . ?
O2 C14 C11 112.6(2) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
C6 C16 H16 115.7 . . ?
C6 C16 C17 128.7(2) . . ?
C17 C16 H16 115.7 . . ?
C18 C17 C16 123.6(2) . . ?
C22 C17 C16 118.6(2) . . ?
C22 C17 C18 117.8(2) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.5 . . ?
C20 C19 C18 120.9(2) . . ?
C20 C19 H19 119.5 . . ?
C19 C20 H20 120.4 . . ?
C19 C20 C21 119.1(2) . . ?
C21 C20 H20 120.4 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 H22 119.1 . . ?
C21 C22 C17 121.7(2) . . ?
C21 C22 H22 119.1 . . ?
C14 O2 C15 115.9(2) . . ?

_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_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.
;
_shelxl_version_number           2013-3
_database_code_depnum_ccdc_archive 'CCDC 984186'
