# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_140107_zyb_5_21_1a
_database_code_depnum_ccdc_archive 'CCDC 1557744'
_audit_update_record             
;
2017-06-22 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2015-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H15 Br O2'
_chemical_formula_sum            'C13 H15 Br O2'
_chemical_formula_weight         283.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 o10 Br1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   9.0905(2)
_cell_length_b                   12.8885(3)
_cell_length_c                   10.5064(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.194(3)
_cell_angle_gamma                90.00
_cell_volume                     1182.12(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.2839
_cell_measurement_theta_min      3.4263
_exptl_absorpt_coefficient_mu    4.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.39
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0373
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8841
_diffrn_reflns_theta_full        67.40
_diffrn_reflns_theta_max         67.40
_diffrn_reflns_theta_min         5.07
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1090773000
_diffrn_orient_matrix_UB_12      0.0466182000
_diffrn_orient_matrix_UB_13      -0.1263362000
_diffrn_orient_matrix_UB_21      0.0327041000
_diffrn_orient_matrix_UB_22      0.1094717000
_diffrn_orient_matrix_UB_23      0.0601472000
_diffrn_orient_matrix_UB_31      0.1347960000
_diffrn_orient_matrix_UB_32      0.0112490000
_diffrn_orient_matrix_UB_33      -0.0611505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1921
_reflns_number_total             2109
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.551
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+1.5102P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1253
_refine_ls_wR_factor_ref         0.1294
_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:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Br1 Br 0.00479(5) 0.84483(4) 0.08454(5) 0.0651(2) Uani 1 d . . .
O1 O 0.0231(3) 0.6009(2) 0.1253(3) 0.0543(7) Uani 1 d . . .
O2 O 0.4107(3) 0.6215(2) -0.0906(2) 0.0504(6) Uani 1 d . . .
C1 C 0.1652(4) 0.7506(3) 0.0826(3) 0.0367(7) Uani 1 d . . .
C2 C 0.1145(4) 0.6404(3) 0.0461(4) 0.0412(8) Uani 1 d . . .
H2 H 0.0508 0.6409 -0.0461 0.049 Uiso 1 calc . . R
C3 C 0.2535(4) 0.5697(3) 0.0530(3) 0.0387(7) Uani 1 d . . .
H3 H 0.2234 0.5070 -0.0006 0.046 Uiso 1 calc . . R
C4 C 0.3430(4) 0.5429(2) 0.1976(3) 0.0370(7) Uani 1 d . . .
H4 H 0.4048 0.4809 0.1957 0.044 Uiso 1 calc . . R
C5 C 0.4541(4) 0.6357(2) 0.2458(3) 0.0323(7) Uani 1 d . . .
H5 H 0.4244 0.6738 0.3155 0.039 Uiso 1 calc . . R
C6 C 0.4366(4) 0.7070(2) 0.1227(3) 0.0310(6) Uani 1 d . . .
C7 C 0.3084(4) 0.7832(2) 0.1128(3) 0.0348(7) Uani 1 d . . .
H7 H 0.3301 0.8534 0.1279 0.042 Uiso 1 calc . . R
C8 C 0.1061(5) 0.5952(3) 0.2616(4) 0.0521(10) Uani 1 d . . .
H8A H 0.0375 0.5740 0.3129 0.063 Uiso 1 calc . . R
H8B H 0.1458 0.6634 0.2923 0.063 Uiso 1 calc . . R
C9 C 0.2369(5) 0.5193(3) 0.2839(4) 0.0526(10) Uani 1 d . . .
H9A H 0.1960 0.4497 0.2644 0.063 Uiso 1 calc . . R
H9B H 0.2956 0.5212 0.3764 0.063 Uiso 1 calc . . R
C10 C 0.3717(4) 0.6309(2) 0.0095(3) 0.0338(7) Uani 1 d . . .
C11 C 0.6261(4) 0.6125(3) 0.2904(4) 0.0484(9) Uani 1 d . . .
H11A H 0.6515 0.5553 0.2403 0.058 Uiso 1 calc . . R
H11B H 0.6597 0.5957 0.3841 0.058 Uiso 1 calc . . R
C12 C 0.6993(5) 0.7148(4) 0.2614(5) 0.0610(11) Uani 1 d . . .
H12A H 0.7033 0.7656 0.3304 0.073 Uiso 1 calc . . R
H12B H 0.8023 0.7029 0.2548 0.073 Uiso 1 calc . . R
C13 C 0.5953(4) 0.7507(3) 0.1307(4) 0.0481(9) Uani 1 d . . .
H13A H 0.6312 0.7250 0.0579 0.058 Uiso 1 calc . . R
H13B H 0.5922 0.8259 0.1267 0.058 Uiso 1 calc . . R


_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
Br1 C1 1.902(3) . ?
O1 C2 1.424(5) . ?
O1 C8 1.422(5) . ?
O2 C10 1.206(4) . ?
C1 C2 1.508(5) . ?
C1 C7 1.320(5) . ?
C2 H2 0.9800 . ?
C2 C3 1.543(5) . ?
C3 H3 0.9800 . ?
C3 C4 1.549(5) . ?
C3 C10 1.504(5) . ?
C4 H4 0.9800 . ?
C4 C5 1.556(5) . ?
C4 C9 1.528(5) . ?
C5 H5 0.9800 . ?
C5 C6 1.558(4) . ?
C5 C11 1.532(5) . ?
C6 C7 1.506(4) . ?
C6 C10 1.527(4) . ?
C6 C13 1.530(5) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.507(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.546(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.506(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 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
C8 O1 C2 112.0(3) . . ?
C2 C1 Br1 115.0(2) . . ?
C7 C1 Br1 120.1(3) . . ?
C7 C1 C2 124.9(3) . . ?
O1 C2 C1 112.0(3) . . ?
O1 C2 H2 107.5 . . ?
O1 C2 C3 111.4(3) . . ?
C1 C2 H2 107.5 . . ?
C1 C2 C3 110.8(3) . . ?
C3 C2 H2 107.5 . . ?
C2 C3 H3 111.5 . . ?
C2 C3 C4 112.2(3) . . ?
C4 C3 H3 111.5 . . ?
C10 C3 C2 108.7(3) . . ?
C10 C3 H3 111.5 . . ?
C10 C3 C4 101.0(3) . . ?
C3 C4 H4 108.1 . . ?
C3 C4 C5 105.3(2) . . ?
C5 C4 H4 108.1 . . ?
C9 C4 C3 112.3(3) . . ?
C9 C4 H4 108.1 . . ?
C9 C4 C5 114.8(3) . . ?
C4 C5 H5 109.9 . . ?
C4 C5 C6 106.0(2) . . ?
C6 C5 H5 109.9 . . ?
C11 C5 C4 117.6(3) . . ?
C11 C5 H5 109.9 . . ?
C11 C5 C6 103.2(3) . . ?
C7 C6 C5 109.9(2) . . ?
C7 C6 C10 104.0(3) . . ?
C7 C6 C13 117.6(3) . . ?
C10 C6 C5 101.3(2) . . ?
C10 C6 C13 115.7(3) . . ?
C13 C6 C5 107.2(3) . . ?
C1 C7 C6 120.1(3) . . ?
C1 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
O1 C8 H8A 109.4 . . ?
O1 C8 H8B 109.4 . . ?
O1 C8 C9 111.3(3) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C4 C9 H9A 109.1 . . ?
C4 C9 H9B 109.1 . . ?
C8 C9 C4 112.3(3) . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O2 C10 C3 128.4(3) . . ?
O2 C10 C6 126.9(3) . . ?
C3 C10 C6 104.7(2) . . ?
C5 C11 H11A 111.1 . . ?
C5 C11 H11B 111.1 . . ?
C5 C11 C12 103.4(3) . . ?
H11A C11 H11B 109.1 . . ?
C12 C11 H11A 111.1 . . ?
C12 C11 H11B 111.1 . . ?
C11 C12 H12A 110.9 . . ?
C11 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C11 104.3(3) . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
C6 C13 H13A 110.5 . . ?
C6 C13 H13B 110.5 . . ?
C12 C13 C6 106.2(3) . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
H13A C13 H13B 108.7 . . ?

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
Br1 C1 C2 O1 -52.6(4) . . . . ?
Br1 C1 C2 C3 -177.7(2) . . . . ?
Br1 C1 C7 C6 174.7(2) . . . . ?
O1 C2 C3 C4 -49.7(4) . . . . ?
O1 C2 C3 C10 -160.6(3) . . . . ?
O1 C8 C9 C4 54.5(5) . . . . ?
C1 C2 C3 C4 75.7(4) . . . . ?
C1 C2 C3 C10 -35.1(4) . . . . ?
C2 O1 C8 C9 -64.1(4) . . . . ?
C2 C1 C7 C6 -4.8(5) . . . . ?
C2 C3 C4 C5 -84.2(3) . . . . ?
C2 C3 C4 C9 41.4(4) . . . . ?
C2 C3 C10 O2 -110.1(4) . . . . ?
C2 C3 C10 C6 71.5(3) . . . . ?
C3 C4 C5 C6 -5.8(3) . . . . ?
C3 C4 C5 C11 -120.5(3) . . . . ?
C3 C4 C9 C8 -43.8(4) . . . . ?
C4 C3 C10 O2 131.8(4) . . . . ?
C4 C3 C10 C6 -46.6(3) . . . . ?
C4 C5 C6 C7 87.8(3) . . . . ?
C4 C5 C6 C10 -21.7(3) . . . . ?
C4 C5 C6 C13 -143.3(3) . . . . ?
C4 C5 C11 C12 151.9(3) . . . . ?
C5 C4 C9 C8 76.5(4) . . . . ?
C5 C6 C7 C1 -68.8(4) . . . . ?
C5 C6 C10 O2 -135.6(4) . . . . ?
C5 C6 C10 C3 42.8(3) . . . . ?
C5 C6 C13 C12 -5.4(4) . . . . ?
C5 C11 C12 C13 -39.8(4) . . . . ?
C6 C5 C11 C12 35.6(4) . . . . ?
C7 C1 C2 O1 126.9(4) . . . . ?
C7 C1 C2 C3 1.8(5) . . . . ?
C7 C6 C10 O2 110.4(4) . . . . ?
C7 C6 C10 C3 -71.2(3) . . . . ?
C7 C6 C13 C12 118.9(4) . . . . ?
C8 O1 C2 C1 -63.3(4) . . . . ?
C8 O1 C2 C3 61.5(4) . . . . ?
C9 C4 C5 C6 -129.9(3) . . . . ?
C9 C4 C5 C11 115.4(4) . . . . ?
C10 C3 C4 C5 31.4(3) . . . . ?
C10 C3 C4 C9 157.1(3) . . . . ?
C10 C6 C7 C1 38.9(4) . . . . ?
C10 C6 C13 C12 -117.5(4) . . . . ?
C11 C5 C6 C7 -147.9(3) . . . . ?
C11 C5 C6 C10 102.6(3) . . . . ?
C11 C5 C6 C13 -19.1(3) . . . . ?
C11 C12 C13 C6 27.6(4) . . . . ?
C13 C6 C7 C1 168.2(3) . . . . ?
C13 C6 C10 O2 -20.1(5) . . . . ?
C13 C6 C10 C3 158.3(3) . . . . ?

####################################################################### 
# 
# 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_160104_zyb_4_124
_database_code_depnum_ccdc_archive 'CCDC 1543770'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-01-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H20 O3'
_chemical_formula_sum            'C15 H20 O3'
_chemical_formula_weight         248.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8'
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           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.4777(10)
_cell_length_b                   8.9184(7)
_cell_length_c                   12.9080(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.233(8)
_cell_angle_gamma                90.00
_cell_volume                     1313.48(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    868
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3297
_cell_measurement_theta_min      3.1688
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.38
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2525
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.18
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0105808000
_diffrn_orient_matrix_UB_12      0.0330295000
_diffrn_orient_matrix_UB_13      0.0501050000
_diffrn_orient_matrix_UB_21      0.0015759000
_diffrn_orient_matrix_UB_22      -0.0722251000
_diffrn_orient_matrix_UB_23      0.0231299000
_diffrn_orient_matrix_UB_31      0.0612505000
_diffrn_orient_matrix_UB_32      -0.0039400000
_diffrn_orient_matrix_UB_33      -0.0031652000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1047
_reflns_number_total             1203
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.102
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(14)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         1203
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0394P)²+0.0847P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0764
_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:
  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), C5(H5), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C11(H11A,H11B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.91113(17) 0.9830(2) 0.37024(14) 0.0536(5) Uani 1 d . . .
O2 O 0.54783(18) 0.9426(3) 0.50273(17) 0.0641(6) Uani 1 d . . .
O3 O 0.65441(17) 0.9476(2) 0.31104(14) 0.0557(5) Uani 1 d . . .
C1 C 0.9597(2) 0.8360(4) 0.3856(2) 0.0541(8) Uani 1 d . . .
H1A H 0.9849 0.8209 0.4591 0.065 Uiso 1 calc . . R
H1B H 1.0278 0.8265 0.3477 0.065 Uiso 1 calc . . R
C2 C 0.8712(2) 0.7181(3) 0.3487(2) 0.0489(7) Uani 1 d . . .
H2A H 0.9056 0.6196 0.3615 0.059 Uiso 1 calc . . R
H2B H 0.8505 0.7287 0.2742 0.059 Uiso 1 calc . . R
C3 C 0.7609(2) 0.7306(3) 0.40389(18) 0.0364(5) Uani 1 d . . .
H3 H 0.7001 0.6687 0.3658 0.044 Uiso 1 calc . . R
C4 C 0.7150(2) 0.8938(3) 0.40461(19) 0.0380(6) Uani 1 d . . .
C5 C 0.8165(2) 1.0065(3) 0.4313(2) 0.0428(6) Uani 1 d . . .
H5 H 0.7846 1.1058 0.4120 0.051 Uiso 1 calc . . R
C6 C 0.8572(2) 1.0136(3) 0.54559(19) 0.0419(6) Uani 1 d . . .
H6 H 0.9152 1.0827 0.5683 0.050 Uiso 1 calc . . R
C7 C 0.8151(2) 0.9270(3) 0.61582(19) 0.0400(6) Uani 1 d . . .
H7 H 0.8425 0.9374 0.6859 0.048 Uiso 1 calc . . R
C8 C 0.7224(2) 0.8113(3) 0.58244(18) 0.0380(6) Uani 1 d . . .
C9 C 0.7724(2) 0.6822(2) 0.51934(18) 0.0341(5) Uani 1 d . . .
H9 H 0.8551 0.6657 0.5443 0.041 Uiso 1 calc . . R
C10 C 0.7001(2) 0.5458(3) 0.5452(2) 0.0436(6) Uani 1 d . . .
H10 H 0.6231 0.5531 0.5045 0.052 Uiso 1 calc . . R
C11 C 0.6835(3) 0.5706(3) 0.6596(2) 0.0555(7) Uani 1 d . . .
H11A H 0.6178 0.5124 0.6789 0.067 Uiso 1 calc . . R
H11B H 0.7534 0.5418 0.7042 0.067 Uiso 1 calc . . R
C12 C 0.6600(3) 0.7378(3) 0.6690(2) 0.0524(7) Uani 1 d . . .
H12A H 0.6916 0.7749 0.7370 0.063 Uiso 1 calc . . R
H12B H 0.5765 0.7583 0.6590 0.063 Uiso 1 calc . . R
C13 C 0.6444(2) 0.8913(3) 0.49823(19) 0.0399(6) Uani 1 d . . .
C14 C 0.5605(3) 0.8582(4) 0.2632(3) 0.0700(9) Uani 1 d . . .
H14A H 0.5123 0.8254 0.3151 0.105 Uiso 1 calc . . GR
H14B H 0.5918 0.7724 0.2308 0.105 Uiso 1 calc . . GR
H14C H 0.5142 0.9165 0.2114 0.105 Uiso 1 calc . . GR
C15 C 0.7540(3) 0.3966(3) 0.5202(3) 0.0670(9) Uani 1 d . . .
H15A H 0.8294 0.3865 0.5598 0.100 Uiso 1 calc . . GR
H15B H 0.7630 0.3924 0.4472 0.100 Uiso 1 calc . . GR
H15C H 0.7038 0.3165 0.5377 0.100 Uiso 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 C1 1.430(4) . ?
O1 C5 1.425(3) . ?
O2 C13 1.207(3) . ?
O3 C4 1.411(3) . ?
O3 C14 1.427(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.503(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.522(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.548(3) . ?
C3 C9 1.543(3) . ?
C4 C5 1.549(4) . ?
C4 C13 1.526(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.500(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.322(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.511(3) . ?
C8 C9 1.555(3) . ?
C8 C12 1.538(4) . ?
C8 C13 1.510(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.530(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.524(4) . ?
C10 C15 1.517(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.523(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C5 O1 C1 111.52(18) . . ?
C4 O3 C14 117.3(2) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.0(2) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.6(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3 107.9 . . ?
C2 C3 C4 111.9(2) . . ?
C2 C3 C9 116.3(2) . . ?
C4 C3 H3 107.9 . . ?
C9 C3 H3 107.9 . . ?
C9 C3 C4 104.51(18) . . ?
O3 C4 C3 116.83(19) . . ?
O3 C4 C5 104.97(19) . . ?
O3 C4 C13 115.3(2) . . ?
C3 C4 C5 111.3(2) . . ?
C13 C4 C3 101.63(19) . . ?
C13 C4 C5 106.52(19) . . ?
O1 C5 C4 112.4(2) . . ?
O1 C5 H5 106.2 . . ?
O1 C5 C6 112.1(2) . . ?
C4 C5 H5 106.2 . . ?
C6 C5 C4 113.1(2) . . ?
C6 C5 H5 106.2 . . ?
C5 C6 H6 118.2 . . ?
C7 C6 C5 123.5(2) . . ?
C7 C6 H6 118.2 . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C9 111.5(2) . . ?
C7 C8 C12 116.9(2) . . ?
C12 C8 C9 107.0(2) . . ?
C13 C8 C7 103.1(2) . . ?
C13 C8 C9 101.33(19) . . ?
C13 C8 C12 116.0(2) . . ?
C3 C9 C8 107.52(18) . . ?
C3 C9 H9 109.7 . . ?
C8 C9 H9 109.7 . . ?
C10 C9 C3 116.2(2) . . ?
C10 C9 C8 103.55(19) . . ?
C10 C9 H9 109.7 . . ?
C9 C10 H10 108.0 . . ?
C11 C10 C9 102.9(2) . . ?
C11 C10 H10 108.0 . . ?
C15 C10 C9 114.0(2) . . ?
C15 C10 H10 108.0 . . ?
C15 C10 C11 115.5(3) . . ?
C10 C11 H11A 110.7 . . ?
C10 C11 H11B 110.7 . . ?
H11A C11 H11B 108.8 . . ?
C12 C11 C10 105.2(2) . . ?
C12 C11 H11A 110.7 . . ?
C12 C11 H11B 110.7 . . ?
C8 C12 H12A 110.8 . . ?
C8 C12 H12B 110.8 . . ?
C11 C12 C8 105.0(2) . . ?
C11 C12 H12A 110.8 . . ?
C11 C12 H12B 110.8 . . ?
H12A C12 H12B 108.8 . . ?
O2 C13 C4 127.0(2) . . ?
O2 C13 C8 128.4(2) . . ?
C8 C13 C4 104.6(2) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -57.6(3) . . . . ?
O1 C5 C6 C7 -125.0(3) . . . . ?
O3 C4 C5 O1 -77.9(2) . . . . ?
O3 C4 C5 C6 154.0(2) . . . . ?
O3 C4 C13 O2 -7.4(4) . . . . ?
O3 C4 C13 C8 172.7(2) . . . . ?
C1 O1 C5 C4 -59.8(3) . . . . ?
C1 O1 C5 C6 68.9(3) . . . . ?
C1 C2 C3 C4 48.0(3) . . . . ?
C1 C2 C3 C9 -72.0(3) . . . . ?
C2 C3 C4 O3 77.0(3) . . . . ?
C2 C3 C4 C5 -43.5(3) . . . . ?
C2 C3 C4 C13 -156.6(2) . . . . ?
C2 C3 C9 C8 129.1(2) . . . . ?
C2 C3 C9 C10 -115.5(2) . . . . ?
C3 C4 C5 O1 49.4(3) . . . . ?
C3 C4 C5 C6 -78.8(2) . . . . ?
C3 C4 C13 O2 -134.8(3) . . . . ?
C3 C4 C13 C8 45.3(2) . . . . ?
C3 C9 C10 C11 -154.4(2) . . . . ?
C3 C9 C10 C15 79.7(3) . . . . ?
C4 C3 C9 C8 5.2(2) . . . . ?
C4 C3 C9 C10 120.6(2) . . . . ?
C4 C5 C6 C7 3.3(4) . . . . ?
C5 O1 C1 C2 63.9(3) . . . . ?
C5 C4 C13 O2 108.7(3) . . . . ?
C5 C4 C13 C8 -71.3(2) . . . . ?
C5 C6 C7 C8 1.1(4) . . . . ?
C6 C7 C8 C9 68.5(3) . . . . ?
C6 C7 C8 C12 -167.9(2) . . . . ?
C6 C7 C8 C13 -39.4(3) . . . . ?
C7 C8 C9 C3 -87.3(2) . . . . ?
C7 C8 C9 C10 149.2(2) . . . . ?
C7 C8 C12 C11 -121.5(3) . . . . ?
C7 C8 C13 O2 -105.9(3) . . . . ?
C7 C8 C13 C4 74.1(2) . . . . ?
C8 C9 C10 C11 -36.8(3) . . . . ?
C8 C9 C10 C15 -162.7(3) . . . . ?
C9 C3 C4 O3 -156.3(2) . . . . ?
C9 C3 C4 C5 83.2(2) . . . . ?
C9 C3 C4 C13 -29.9(2) . . . . ?
C9 C8 C12 C11 4.4(3) . . . . ?
C9 C8 C13 O2 138.6(3) . . . . ?
C9 C8 C13 C4 -41.4(2) . . . . ?
C9 C10 C11 C12 40.5(3) . . . . ?
C10 C11 C12 C8 -27.6(3) . . . . ?
C12 C8 C9 C3 143.7(2) . . . . ?
C12 C8 C9 C10 20.2(3) . . . . ?
C12 C8 C13 O2 23.2(4) . . . . ?
C12 C8 C13 C4 -156.9(2) . . . . ?
C13 C4 C5 O1 159.3(2) . . . . ?
C13 C4 C5 C6 31.2(3) . . . . ?
C13 C8 C9 C3 21.8(2) . . . . ?
C13 C8 C9 C10 -101.7(2) . . . . ?
C13 C8 C12 C11 116.6(3) . . . . ?
C14 O3 C4 C3 51.5(3) . . . . ?
C14 O3 C4 C5 175.3(2) . . . . ?
C14 O3 C4 C13 -67.8(3) . . . . ?
C15 C10 C11 C12 165.5(2) . . . . ?

####################################################################### 
# 
# 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_160311_wbn_10162
_database_code_depnum_ccdc_archive 'CCDC 1543772'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-03-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H26 O2'
_chemical_formula_sum            'C20 H26 O2'
_chemical_formula_weight         298.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 o10'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.1485(5)
_cell_length_b                   8.5900(7)
_cell_length_c                   16.0047(11)
_cell_angle_alpha                95.985(6)
_cell_angle_beta                 95.246(6)
_cell_angle_gamma                101.426(7)
_cell_volume                     818.57(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1417
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.3692
_cell_measurement_theta_min      3.3962
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.36
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0474
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5115
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         3.40
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0775797000
_diffrn_orient_matrix_UB_12      0.0438531000
_diffrn_orient_matrix_UB_13      -0.0158910000
_diffrn_orient_matrix_UB_21      0.0853245000
_diffrn_orient_matrix_UB_22      0.0468941000
_diffrn_orient_matrix_UB_23      -0.0191704000
_diffrn_orient_matrix_UB_31      -0.0271744000
_diffrn_orient_matrix_UB_32      -0.0555691000
_diffrn_orient_matrix_UB_33      -0.0373130000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2132
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_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     203
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0504
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0464P)²+0.1935P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1298
_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:
  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), C6(H6), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.2971(3) 0.6880(3) 0.48272(11) 0.0977(8) Uani 1 d . . .
O2 O 0.3851(2) 0.74889(19) 0.22757(9) 0.0534(4) Uani 1 d . . .
C1 C 0.1934(4) 0.7117(3) 0.41946(13) 0.0513(6) Uani 1 d . . .
C2 C -0.0433(3) 0.6231(2) 0.39216(11) 0.0433(5) Uani 1 d . . .
H2A H -0.1412 0.6788 0.4222 0.052 Uiso 1 calc . . R
H2B H -0.0597 0.5177 0.4105 0.052 Uiso 1 calc . . R
C3 C -0.1280(3) 0.6010(2) 0.29607(10) 0.0310(4) Uani 1 d . . .
H3 H -0.2847 0.6106 0.2928 0.037 Uiso 1 calc . . R
C4 C -0.0058(3) 0.7416(2) 0.25169(11) 0.0307(4) Uani 1 d . . .
C5 C 0.2467(3) 0.7656(2) 0.27387(12) 0.0371(5) Uani 1 d . . .
C6 C 0.2886(3) 0.8390(3) 0.36587(12) 0.0444(5) Uani 1 d . . .
H6 H 0.4449 0.8907 0.3844 0.053 Uiso 1 calc . . R
C7 C 0.1328(3) 0.9556(2) 0.36111(12) 0.0396(5) Uani 1 d . . .
C8 C -0.0302(3) 0.8986(2) 0.29866(11) 0.0372(5) Uani 1 d . . .
H8 H -0.1466 0.9494 0.2852 0.045 Uiso 1 calc . . R
C9 C -0.0808(3) 0.7217(2) 0.15697(11) 0.0372(5) Uani 1 d . . .
H9A H -0.2282 0.7458 0.1483 0.045 Uiso 1 calc . . R
H9B H 0.0207 0.7986 0.1309 0.045 Uiso 1 calc . . R
C10 C -0.0884(3) 0.5541(2) 0.11315(11) 0.0374(5) Uani 1 d . . .
H10A H -0.1495 0.5460 0.0544 0.045 Uiso 1 calc . . R
H10B H 0.0620 0.5346 0.1145 0.045 Uiso 1 calc . . R
C11 C -0.2319(3) 0.4284(2) 0.15674(10) 0.0314(4) Uani 1 d . . .
H11 H -0.3704 0.4670 0.1619 0.038 Uiso 1 calc . . R
C12 C -0.1301(3) 0.4310(2) 0.24985(11) 0.0309(4) Uani 1 d . . .
C13 C -0.2832(3) 0.3066(2) 0.28926(12) 0.0399(5) Uani 1 d . . .
H13 H -0.2727 0.3153 0.3480 0.048 Uiso 1 calc . . R
C14 C -0.4308(3) 0.1865(2) 0.24590(13) 0.0425(5) Uani 1 d . . .
H14 H -0.5136 0.1145 0.2764 0.051 Uiso 1 calc . . R
C15 C -0.4759(3) 0.1567(3) 0.15250(13) 0.0490(6) Uani 1 d . . .
H15A H -0.6239 0.1746 0.1361 0.059 Uiso 1 calc . . R
H15B H -0.4774 0.0450 0.1347 0.059 Uiso 1 calc . . R
C16 C -0.3087(3) 0.2601(2) 0.10462(11) 0.0375(5) Uani 1 d . . .
C17 C 0.1688(4) 1.1034(3) 0.42308(14) 0.0592(7) Uani 1 d . . .
H17A H 0.3033 1.1754 0.4144 0.089 Uiso 1 calc . . GR
H17B H 0.1818 1.0754 0.4796 0.089 Uiso 1 calc . . GR
H17C H 0.0444 1.1546 0.4151 0.089 Uiso 1 calc . . GR
C18 C 0.1067(3) 0.3946(2) 0.25979(12) 0.0422(5) Uani 1 d . . .
H18A H 0.0966 0.2815 0.2471 0.063 Uiso 1 calc . . GR
H18B H 0.1745 0.4296 0.3169 0.063 Uiso 1 calc . . GR
H18C H 0.1960 0.4502 0.2216 0.063 Uiso 1 calc . . GR
C19 C -0.1180(4) 0.1759(3) 0.08655(14) 0.0552(6) Uani 1 d . . .
H19A H -0.0013 0.2488 0.0661 0.083 Uiso 1 calc . . GR
H19B H -0.1727 0.0848 0.0446 0.083 Uiso 1 calc . . GR
H19C H -0.0603 0.1413 0.1376 0.083 Uiso 1 calc . . GR
C20 C -0.4334(4) 0.2761(3) 0.01890(13) 0.0577(6) Uani 1 d . . .
H20A H -0.5419 0.3407 0.0280 0.086 Uiso 1 calc . . GR
H20B H -0.5076 0.1718 -0.0084 0.086 Uiso 1 calc . . GR
H20C H -0.3286 0.3256 -0.0163 0.086 Uiso 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 C1 1.204(2) . ?
O2 C5 1.198(2) . ?
C1 C2 1.505(3) . ?
C1 C6 1.519(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.558(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.564(2) . ?
C3 C12 1.563(2) . ?
C4 C5 1.529(3) . ?
C4 C8 1.515(3) . ?
C4 C9 1.525(2) . ?
C5 C6 1.518(3) . ?
C6 H6 0.9800 . ?
C6 C7 1.520(3) . ?
C7 C8 1.328(3) . ?
C7 C17 1.494(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.525(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.524(2) . ?
C11 H11 0.9800 . ?
C11 C12 1.559(2) . ?
C11 C16 1.554(2) . ?
C12 C13 1.509(2) . ?
C12 C18 1.546(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.317(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.481(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.536(3) . ?
C16 C19 1.528(3) . ?
C16 C20 1.542(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O1 C1 C2 121.5(2) . . ?
O1 C1 C6 122.0(2) . . ?
C2 C1 C6 116.37(17) . . ?
C1 C2 H2A 107.9 . . ?
C1 C2 H2B 107.9 . . ?
C1 C2 C3 117.58(16) . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 H2A 107.9 . . ?
C3 C2 H2B 107.9 . . ?
C2 C3 H3 105.7 . . ?
C2 C3 C4 111.06(14) . . ?
C2 C3 C12 113.85(15) . . ?
C4 C3 H3 105.7 . . ?
C12 C3 H3 105.7 . . ?
C12 C3 C4 113.95(14) . . ?
C5 C4 C3 109.77(15) . . ?
C8 C4 C3 108.74(14) . . ?
C8 C4 C5 96.56(14) . . ?
C8 C4 C9 114.16(16) . . ?
C9 C4 C3 112.47(14) . . ?
C9 C4 C5 114.01(15) . . ?
O2 C5 C4 128.36(17) . . ?
O2 C5 C6 126.74(18) . . ?
C6 C5 C4 104.37(16) . . ?
C1 C6 H6 113.7 . . ?
C1 C6 C7 108.11(17) . . ?
C5 C6 C1 108.27(16) . . ?
C5 C6 H6 113.7 . . ?
C5 C6 C7 98.03(15) . . ?
C7 C6 H6 113.7 . . ?
C8 C7 C6 109.02(17) . . ?
C8 C7 C17 129.7(2) . . ?
C17 C7 C6 121.22(18) . . ?
C4 C8 H8 123.7 . . ?
C7 C8 C4 112.63(18) . . ?
C7 C8 H8 123.7 . . ?
C4 C9 H9A 108.9 . . ?
C4 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C4 113.35(16) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 C9 110.58(15) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
C10 C11 H11 104.4 . . ?
C10 C11 C12 110.87(14) . . ?
C10 C11 C16 115.37(14) . . ?
C12 C11 H11 104.4 . . ?
C16 C11 H11 104.4 . . ?
C16 C11 C12 115.73(15) . . ?
C11 C12 C3 106.44(14) . . ?
C13 C12 C3 109.34(14) . . ?
C13 C12 C11 107.80(14) . . ?
C13 C12 C18 107.92(15) . . ?
C18 C12 C3 110.33(14) . . ?
C18 C12 C11 114.90(15) . . ?
C12 C13 H13 117.9 . . ?
C14 C13 C12 124.23(17) . . ?
C14 C13 H13 117.9 . . ?
C13 C14 H14 117.3 . . ?
C13 C14 C15 125.41(18) . . ?
C15 C14 H14 117.3 . . ?
C14 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C14 C15 C16 115.32(16) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C15 C16 C11 108.20(15) . . ?
C15 C16 C20 107.30(16) . . ?
C19 C16 C11 114.17(15) . . ?
C19 C16 C15 110.04(18) . . ?
C19 C16 C20 107.68(17) . . ?
C20 C16 C11 109.24(17) . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C18 H18A 109.5 . . ?
C12 C18 H18B 109.5 . . ?
C12 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -153.5(2) . . . . ?
O1 C1 C6 C5 133.3(3) . . . . ?
O1 C1 C6 C7 -121.5(3) . . . . ?
O2 C5 C6 C1 -117.8(2) . . . . ?
O2 C5 C6 C7 130.0(2) . . . . ?
C1 C2 C3 C4 -29.2(2) . . . . ?
C1 C2 C3 C12 101.0(2) . . . . ?
C1 C6 C7 C8 -85.26(19) . . . . ?
C1 C6 C7 C17 92.2(2) . . . . ?
C2 C1 C6 C5 -50.2(3) . . . . ?
C2 C1 C6 C7 55.0(2) . . . . ?
C2 C3 C4 C5 50.6(2) . . . . ?
C2 C3 C4 C8 -53.9(2) . . . . ?
C2 C3 C4 C9 178.62(16) . . . . ?
C2 C3 C12 C11 176.72(14) . . . . ?
C2 C3 C12 C13 60.5(2) . . . . ?
C2 C3 C12 C18 -58.0(2) . . . . ?
C3 C4 C5 O2 116.0(2) . . . . ?
C3 C4 C5 C6 -71.99(18) . . . . ?
C3 C4 C8 C7 89.12(18) . . . . ?
C3 C4 C9 C10 -46.8(2) . . . . ?
C3 C12 C13 C14 134.9(2) . . . . ?
C4 C3 C12 C11 -54.50(18) . . . . ?
C4 C3 C12 C13 -170.69(15) . . . . ?
C4 C3 C12 C18 70.77(19) . . . . ?
C4 C5 C6 C1 70.0(2) . . . . ?
C4 C5 C6 C7 -42.17(17) . . . . ?
C4 C9 C10 C11 54.2(2) . . . . ?
C5 C4 C8 C7 -24.37(19) . . . . ?
C5 C4 C9 C10 79.0(2) . . . . ?
C5 C6 C7 C8 27.03(19) . . . . ?
C5 C6 C7 C17 -155.50(18) . . . . ?
C6 C1 C2 C3 30.0(3) . . . . ?
C6 C7 C8 C4 -1.6(2) . . . . ?
C8 C4 C5 O2 -131.4(2) . . . . ?
C8 C4 C5 C6 40.65(17) . . . . ?
C8 C4 C9 C10 -171.28(15) . . . . ?
C9 C4 C5 O2 -11.2(3) . . . . ?
C9 C4 C5 C6 160.80(16) . . . . ?
C9 C4 C8 C7 -144.40(17) . . . . ?
C9 C10 C11 C12 -62.7(2) . . . . ?
C9 C10 C11 C16 163.28(16) . . . . ?
C10 C11 C12 C3 61.56(18) . . . . ?
C10 C11 C12 C13 178.78(15) . . . . ?
C10 C11 C12 C18 -60.9(2) . . . . ?
C10 C11 C16 C15 -172.34(17) . . . . ?
C10 C11 C16 C19 64.8(2) . . . . ?
C10 C11 C16 C20 -55.8(2) . . . . ?
C11 C12 C13 C14 19.6(3) . . . . ?
C12 C3 C4 C5 -79.63(18) . . . . ?
C12 C3 C4 C8 175.89(15) . . . . ?
C12 C3 C4 C9 48.4(2) . . . . ?
C12 C11 C16 C15 55.9(2) . . . . ?
C12 C11 C16 C19 -67.0(2) . . . . ?
C12 C11 C16 C20 172.38(16) . . . . ?
C12 C13 C14 C15 -2.1(3) . . . . ?
C13 C14 C15 C16 10.4(3) . . . . ?
C14 C15 C16 C11 -35.0(2) . . . . ?
C14 C15 C16 C19 90.4(2) . . . . ?
C14 C15 C16 C20 -152.73(19) . . . . ?
C16 C11 C12 C3 -164.58(14) . . . . ?
C16 C11 C12 C13 -47.4(2) . . . . ?
C16 C11 C12 C18 73.0(2) . . . . ?
C17 C7 C8 C4 -178.74(19) . . . . ?
C18 C12 C13 C14 -105.0(2) . . . . ?

####################################################################### 
# 
# 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_141210_hc_40743a
_database_code_depnum_ccdc_archive 'CCDC 1543771'
_audit_update_record             
;
2017-04-13 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2014-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H16 F6 O3'
_chemical_formula_sum            'C16 H16 F6 O3'
_chemical_formula_weight         370.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h10 n2 o8 F1'
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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.6511(6)
_cell_length_b                   10.6171(17)
_cell_length_c                   11.0543(14)
_cell_angle_alpha                65.681(14)
_cell_angle_beta                 78.962(10)
_cell_angle_gamma                83.688(10)
_cell_volume                     802.66(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1165
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2376
_cell_measurement_theta_min      3.1196
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.3
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0510
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5137
_diffrn_reflns_theta_full        25.35
_diffrn_reflns_theta_max         25.35
_diffrn_reflns_theta_min         3.13
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0165635000
_diffrn_orient_matrix_UB_12      0.0335816000
_diffrn_orient_matrix_UB_13      -0.0711886000
_diffrn_orient_matrix_UB_21      0.0920523000
_diffrn_orient_matrix_UB_22      0.0009554000
_diffrn_orient_matrix_UB_23      0.0016479000
_diffrn_orient_matrix_UB_31      0.0135749000
_diffrn_orient_matrix_UB_32      -0.0652119000
_diffrn_orient_matrix_UB_33      -0.0044859000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1755
_reflns_number_total             2939
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2939
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0646
_refine_ls_restrained_S_all      1.045
_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)+(0.1091P)²+0.0028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1690
_refine_ls_wR_factor_ref         0.2103
_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:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.5830(4) 0.1959(4) 0.2888(3) 0.1470(13) Uani 1 d . . .
F2 F 0.3552(5) 0.2177(3) 0.4211(3) 0.1403(12) Uani 1 d . . .
F3 F 0.3989(6) 0.0382(3) 0.3826(3) 0.1552(14) Uani 1 d . . .
F4 F 0.0405(4) 0.2493(3) 0.3468(2) 0.1155(9) Uani 1 d . . .
F5 F 0.0301(3) 0.2836(3) 0.1456(3) 0.1188(9) Uani 1 d . . .
F6 F 0.0802(4) 0.0822(3) 0.2846(3) 0.1254(10) Uani 1 d . . .
O1 O 0.8111(3) 0.4670(2) -0.2142(3) 0.0794(7) Uani 1 d . . .
O2 O 0.3783(3) 0.18384(19) 0.11190(18) 0.0537(6) Uani 1 d . . .
O3 O 0.3941(3) 0.40742(19) -0.0623(2) 0.0577(6) Uani 1 d . . .
C1 C 0.6665(4) 0.2811(3) -0.0132(3) 0.0504(7) Uani 1 d . . .
H1 H 0.6851 0.3263 0.0446 0.060 Uiso 1 calc . . R
C2 C 0.7597(4) 0.1402(3) 0.0198(3) 0.0553(8) Uani 1 d . . .
H2 H 0.7722 0.0769 0.1062 0.066 Uiso 1 calc . . R
C3 C 0.8202(4) 0.1200(3) -0.0904(3) 0.0541(8) Uani 1 d . . .
H3 H 0.8833 0.0405 -0.0921 0.065 Uiso 1 calc . . R
C4 C 0.7753(4) 0.2404(3) -0.2133(3) 0.0512(7) Uani 1 d . . .
C5 C 0.7582(4) 0.3512(3) -0.1580(3) 0.0535(8) Uani 1 d . . .
C6 C 0.4707(4) 0.2735(3) -0.0196(3) 0.0463(7) Uani 1 d . . .
C7 C 0.4368(3) 0.2107(3) -0.1145(3) 0.0479(7) Uani 1 d . . .
H7 H 0.4201 0.1114 -0.0627 0.058 Uiso 1 calc . . R
C8 C 0.5844(4) 0.2300(3) -0.2376(3) 0.0507(7) Uani 1 d . . .
H8 H 0.5864 0.1468 -0.2555 0.061 Uiso 1 calc . . R
C9 C 0.5764(4) 0.3520(4) -0.3707(3) 0.0699(9) Uani 1 d . . .
H9A H 0.5541 0.4379 -0.3582 0.084 Uiso 1 calc . . R
H9B H 0.4838 0.3416 -0.4145 0.084 Uiso 1 calc . . R
C10 C 0.7600(5) 0.3488(5) -0.4524(4) 0.0945(13) Uani 1 d . . .
H10A H 0.7960 0.4420 -0.5117 0.113 Uiso 1 calc . . R
H10B H 0.7585 0.2968 -0.5067 0.113 Uiso 1 calc . . R
C11 C 0.8889(4) 0.2793(3) -0.3520(3) 0.0654(9) Uani 1 d . . .
H11A H 0.9464 0.1976 -0.3627 0.078 Uiso 1 calc . . R
H11B H 0.9800 0.3425 -0.3648 0.078 Uiso 1 calc . . R
C12 C 0.2553(4) 0.2804(3) -0.1481(3) 0.0638(9) Uani 1 d . . .
H12A H 0.2405 0.2910 -0.2370 0.077 Uiso 1 calc . . R
H12B H 0.1587 0.2268 -0.0827 0.077 Uiso 1 calc . . R
C13 C 0.2595(4) 0.4187(4) -0.1424(4) 0.0705(9) Uani 1 d . . .
H13A H 0.2890 0.4897 -0.2322 0.085 Uiso 1 calc . . R
H13B H 0.1442 0.4428 -0.1014 0.085 Uiso 1 calc . . R
C14 C 0.3123(4) 0.2396(3) 0.2075(3) 0.0609(8) Uani 1 d . . .
H14 H 0.3297 0.3395 0.1667 0.073 Uiso 1 calc . . R
C15 C 0.4121(7) 0.1730(5) 0.3253(4) 0.0879(12) Uani 1 d . . .
C16 C 0.1158(5) 0.2133(4) 0.2477(4) 0.0769(10) Uani 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
F1 C15 1.311(5) . ?
F2 C15 1.315(4) . ?
F3 C15 1.311(5) . ?
F4 C16 1.317(4) . ?
F5 C16 1.321(4) . ?
F6 C16 1.323(4) . ?
O1 C5 1.202(3) . ?
O2 C6 1.460(3) . ?
O2 C14 1.403(3) . ?
O3 C6 1.399(3) . ?
O3 C13 1.446(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.515(4) . ?
C1 C5 1.521(4) . ?
C1 C6 1.526(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.313(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.500(4) . ?
C4 C5 1.517(4) . ?
C4 C8 1.558(4) . ?
C4 C11 1.525(4) . ?
C6 C7 1.527(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.550(4) . ?
C7 C12 1.536(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.514(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.523(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.528(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.499(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14 0.9800 . ?
C14 C15 1.511(5) . ?
C14 C16 1.506(5) . ?

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 O2 C6 119.0(2) . . ?
C6 O3 C13 109.5(2) . . ?
C2 C1 H1 113.6 . . ?
C2 C1 C5 98.1(2) . . ?
C2 C1 C6 110.6(2) . . ?
C5 C1 H1 113.6 . . ?
C5 C1 C6 106.1(2) . . ?
C6 C1 H1 113.6 . . ?
C1 C2 H2 124.7 . . ?
C3 C2 C1 110.6(3) . . ?
C3 C2 H2 124.7 . . ?
C2 C3 H3 124.1 . . ?
C2 C3 C4 111.8(3) . . ?
C4 C3 H3 124.1 . . ?
C3 C4 C5 97.9(2) . . ?
C3 C4 C8 111.1(2) . . ?
C3 C4 C11 123.3(2) . . ?
C5 C4 C8 105.0(2) . . ?
C5 C4 C11 114.4(3) . . ?
C11 C4 C8 104.0(2) . . ?
O1 C5 C1 127.4(3) . . ?
O1 C5 C4 127.9(3) . . ?
C4 C5 C1 104.6(2) . . ?
O2 C6 C1 110.2(2) . . ?
O2 C6 C7 104.2(2) . . ?
O3 C6 O2 111.2(2) . . ?
O3 C6 C1 108.7(2) . . ?
O3 C6 C7 107.5(2) . . ?
C1 C6 C7 115.1(2) . . ?
C6 C7 H7 108.3 . . ?
C6 C7 C8 116.0(2) . . ?
C6 C7 C12 100.2(2) . . ?
C8 C7 H7 108.3 . . ?
C12 C7 H7 108.3 . . ?
C12 C7 C8 115.3(2) . . ?
C4 C8 H8 106.4 . . ?
C7 C8 C4 114.2(2) . . ?
C7 C8 H8 106.4 . . ?
C9 C8 C4 101.5(2) . . ?
C9 C8 C7 120.9(2) . . ?
C9 C8 H8 106.4 . . ?
C8 C9 H9A 111.0 . . ?
C8 C9 H9B 111.0 . . ?
C8 C9 C10 103.9(3) . . ?
H9A C9 H9B 109.0 . . ?
C10 C9 H9A 111.0 . . ?
C10 C9 H9B 111.0 . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
C9 C10 C11 106.9(3) . . ?
H10A C10 H10B 108.6 . . ?
C11 C10 H10A 110.3 . . ?
C11 C10 H10B 110.3 . . ?
C4 C11 C10 105.6(3) . . ?
C4 C11 H11A 110.6 . . ?
C4 C11 H11B 110.6 . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?
C7 C12 H12A 110.9 . . ?
C7 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C13 C12 C7 104.4(2) . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
O3 C13 C12 106.8(2) . . ?
O3 C13 H13A 110.4 . . ?
O3 C13 H13B 110.4 . . ?
C12 C13 H13A 110.4 . . ?
C12 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
O2 C14 H14 109.4 . . ?
O2 C14 C15 109.3(3) . . ?
O2 C14 C16 107.1(3) . . ?
C15 C14 H14 109.4 . . ?
C16 C14 H14 109.4 . . ?
C16 C14 C15 112.4(3) . . ?
F1 C15 F2 106.8(4) . . ?
F1 C15 C14 111.8(3) . . ?
F2 C15 C14 113.0(3) . . ?
F3 C15 F1 106.1(4) . . ?
F3 C15 F2 106.0(4) . . ?
F3 C15 C14 112.7(4) . . ?
F4 C16 F5 106.8(3) . . ?
F4 C16 F6 107.3(3) . . ?
F4 C16 C14 113.2(3) . . ?
F5 C16 F6 105.4(4) . . ?
F5 C16 C14 110.9(3) . . ?
F6 C16 C14 112.9(3) . . ?

