# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1427901'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;


_chemical_formula_sum            'C14 H22 F4 O2'
_chemical_formula_moiety         'C14 H22 F4 O2'
_chemical_formula_weight         298.32
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   9.1961(6)
_cell_length_b                   9.1334(6)
_cell_length_c                   17.5805(11)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.135(2)
_cell_angle_gamma                90.0000
_cell_volume                     1465.18(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9089
_cell_measurement_theta_min      4.84
_cell_measurement_theta_max      67.88
_cell_measurement_temperature    125
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    1.059
_exptl_absorpt_correction_type   none

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      125
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 29.257
_diffrn_reflns_number            18512
_diffrn_reflns_av_R_equivalents  0.0433

_diffrn_reflns_theta_max         68.14
_diffrn_reflns_theta_full        68.14
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             4925
_reflns_number_gt                4311
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1415
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4925
_refine_ls_number_parameters     361
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0610P)²+1.5896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.700
_refine_diff_density_min         -0.290
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;   
 Flack x determined using 1656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.18(7)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
F1 F 0.6336(3) 0.7563(4) 0.65745(17) 0.0363(8) Uani 1.0 2 d . . .
F2 F 0.8461(3) 0.6648(3) 0.70335(17) 0.0353(8) Uani 1.0 2 d . . .
F3 F 0.7304(4) 0.7410(4) 0.95386(17) 0.0418(8) Uani 1.0 2 d . . .
F4 F 0.9354(3) 0.8649(4) 0.97509(16) 0.0386(8) Uani 1.0 2 d . . .
F5 F 0.6152(3) 1.1978(4) 0.15552(17) 0.0405(8) Uani 1.0 2 d . . .
F6 F 0.8236(4) 1.2946(4) 0.20534(18) 0.0393(8) Uani 1.0 2 d . . .
F7 F 0.6763(5) 1.1770(5) 0.4469(3) 0.0646(11) Uani 1.0 2 d . . .
F8 F 0.8955(4) 1.0939(5) 0.47698(18) 0.0555(10) Uani 1.0 2 d . . .
O1 O 0.8037(4) 1.3587(4) 0.78896(17) 0.0243(7) Uani 1.0 2 d . . .
O2 O 0.5715(4) 1.4025(4) 0.7377(2) 0.0338(9) Uani 1.0 2 d . . .
O21 O 0.7595(4) 0.6214(5) 0.28147(19) 0.0359(9) Uani 1.0 2 d . . .
O22 O 0.5518(4) 0.5459(5) 0.2144(3) 0.0403(10) Uani 1.0 2 d . . .
C2 C 0.6949(5) 1.3684(6) 0.7302(3) 0.0228(10) Uani 1.0 2 d . . .
C3 C 0.7491(6) 1.3321(6) 0.6554(3) 0.0262(11) Uani 1.0 2 d . . .
C4 C 0.8354(5) 1.1888(6) 0.6559(3) 0.0245(11) Uani 1.0 2 d . . .
C5 C 0.7442(5) 1.0565(6) 0.6728(3) 0.0246(11) Uani 1.0 2 d . . .
C6 C 0.8348(5) 0.9159(6) 0.6767(3) 0.0245(11) Uani 1.0 2 d . . .
C7 C 0.7577(5) 0.7877(6) 0.7070(3) 0.0264(11) Uani 1.0 2 d . . .
C8 C 0.7139(5) 0.7976(6) 0.7868(3) 0.0250(11) Uani 1.0 2 d . . .
C9 C 0.8466(5) 0.8164(6) 0.8483(3) 0.0253(11) Uani 1.0 2 d . . .
C10 C 0.8051(5) 0.8566(6) 0.9259(3) 0.0278(11) Uani 1.0 2 d . . .
C11 C 0.7201(6) 0.9940(6) 0.9341(3) 0.0256(11) Uani 1.0 2 d . . .
C12 C 0.7935(5) 1.1319(6) 0.9075(3) 0.0263(11) Uani 1.0 2 d . . .
C13 C 0.6950(5) 1.2672(5) 0.9024(3) 0.0221(10) Uani 1.0 2 d . . .
C14 C 0.7664(6) 1.3949(5) 0.8647(3) 0.0257(11) Uani 1.0 2 d . . .
C15 C 0.6578(6) 1.3172(7) 0.9802(3) 0.0369(13) Uani 1.0 2 d . . .
C22 C 0.6745(6) 0.5932(6) 0.2158(3) 0.0294(12) Uani 1.0 2 d . . .
C23 C 0.7482(6) 0.6281(6) 0.1466(3) 0.0286(11) Uani 1.0 2 d . . .
C24 C 0.8315(5) 0.7722(6) 0.1523(3) 0.0261(11) Uani 1.0 2 d . . .
C25 C 0.7355(5) 0.9011(6) 0.1676(3) 0.0275(11) Uani 1.0 2 d . . .
C26 C 0.8214(5) 1.0455(6) 0.1749(3) 0.0277(11) Uani 1.0 2 d . . .
C27 C 0.7386(5) 1.1691(6) 0.2058(3) 0.0292(12) Uani 1.0 2 d . . .
C28 C 0.6908(5) 1.1537(6) 0.2847(3) 0.0288(12) Uani 1.0 2 d . . .
C29 C 0.8195(6) 1.1349(7) 0.3479(3) 0.0332(12) Uani 1.0 2 d . . .
C30 C 0.7749(6) 1.0816(7) 0.4222(4) 0.0389(14) Uani 1.0 2 d . . .
C31 C 0.7140(6) 0.9282(7) 0.4252(3) 0.0366(13) Uani 1.0 2 d . . .
C32 C 0.8308(7) 0.8116(7) 0.4144(4) 0.0428(15) Uani 1.0 2 d . . .
C33 C 0.7852(7) 0.6498(8) 0.4171(4) 0.0446(15) Uani 1.0 2 d . . .
C34 C 0.6839(7) 0.6046(8) 0.3498(3) 0.0485(16) Uani 1.0 2 d . . .
C35 C 0.7134(9) 0.6121(9) 0.4893(4) 0.064(2) Uani 1.0 2 d . . .
H3A H 0.8123 1.4131 0.6415 0.0314 Uiso 1.0 2 calc R . .
H3B H 0.6639 1.3261 0.6151 0.0314 Uiso 1.0 2 calc R . .
H4A H 0.8705 1.1754 0.6053 0.0294 Uiso 1.0 2 calc R . .
H4B H 0.9224 1.1951 0.6950 0.0294 Uiso 1.0 2 calc R . .
H5A H 0.6600 1.0469 0.6322 0.0295 Uiso 1.0 2 calc R . .
H5B H 0.7052 1.0715 0.7222 0.0295 Uiso 1.0 2 calc R . .
H6A H 0.8586 0.8920 0.6248 0.0294 Uiso 1.0 2 calc R . .
H6B H 0.9282 0.9327 0.7101 0.0294 Uiso 1.0 2 calc R . .
H8A H 0.6602 0.7076 0.7977 0.0299 Uiso 1.0 2 calc R . .
H8B H 0.6467 0.8817 0.7893 0.0299 Uiso 1.0 2 calc R . .
H9A H 0.9030 0.7238 0.8528 0.0304 Uiso 1.0 2 calc R . .
H9B H 0.9112 0.8936 0.8315 0.0304 Uiso 1.0 2 calc R . .
H11A H 0.7055 1.0061 0.9886 0.0307 Uiso 1.0 2 calc R . .
H11B H 0.6222 0.9838 0.9041 0.0307 Uiso 1.0 2 calc R . .
H12A H 0.8826 1.1524 0.9436 0.0315 Uiso 1.0 2 calc R . .
H12B H 0.8246 1.1132 0.8565 0.0315 Uiso 1.0 2 calc R . .
H13 H 0.6014 1.2422 0.8698 0.0265 Uiso 1.0 2 calc R . .
H14A H 0.6984 1.4794 0.8605 0.0309 Uiso 1.0 2 calc R . .
H14B H 0.8565 1.4245 0.8979 0.0309 Uiso 1.0 2 calc R . .
H15A H 0.7482 1.3423 1.0132 0.0442 Uiso 1.0 2 calc R . .
H15B H 0.6072 1.2382 1.0039 0.0442 Uiso 1.0 2 calc R . .
H15C H 0.5940 1.4034 0.9736 0.0442 Uiso 1.0 2 calc R . .
H23A H 0.6731 0.6315 0.1011 0.0344 Uiso 1.0 2 calc R . .
H23B H 0.8172 0.5481 0.1386 0.0344 Uiso 1.0 2 calc R . .
H24A H 0.9140 0.7652 0.1940 0.0313 Uiso 1.0 2 calc R . .
H24B H 0.8731 0.7894 0.1038 0.0313 Uiso 1.0 2 calc R . .
H25A H 0.6922 0.8832 0.2156 0.0331 Uiso 1.0 2 calc R . .
H25B H 0.6542 0.9095 0.1253 0.0331 Uiso 1.0 2 calc R . .
H26A H 0.9140 1.0301 0.2091 0.0332 Uiso 1.0 2 calc R . .
H26B H 0.8469 1.0734 0.1238 0.0332 Uiso 1.0 2 calc R . .
H28A H 0.6250 1.0679 0.2850 0.0345 Uiso 1.0 2 calc R . .
H28B H 0.6343 1.2417 0.2959 0.0345 Uiso 1.0 2 calc R . .
H29A H 0.8900 1.0645 0.3302 0.0398 Uiso 1.0 2 calc R . .
H29B H 0.8703 1.2300 0.3568 0.0398 Uiso 1.0 2 calc R . .
H31A H 0.6303 0.9168 0.3844 0.0439 Uiso 1.0 2 calc R . .
H31B H 0.6774 0.9128 0.4752 0.0439 Uiso 1.0 2 calc R . .
H32A H 0.8665 0.8295 0.3644 0.0513 Uiso 1.0 2 calc R . .
H32B H 0.9148 0.8271 0.4546 0.0513 Uiso 1.0 2 calc R . .
H33 H 0.8759 0.5891 0.4182 0.0535 Uiso 1.0 2 calc R . .
H34A H 0.6543 0.5013 0.3554 0.0582 Uiso 1.0 2 calc R . .
H34B H 0.5947 0.6663 0.3451 0.0582 Uiso 1.0 2 calc R . .
H35A H 0.6940 0.5066 0.4904 0.0769 Uiso 1.0 2 calc R . .
H35B H 0.6210 0.6658 0.4884 0.0769 Uiso 1.0 2 calc R . .
H35C H 0.7795 0.6398 0.5351 0.0769 Uiso 1.0 2 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r2 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r2'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r2'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_molecular_graphics    'CrystalStructure 4.0'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C7 1.377(6) yes . .
F2 C7 1.393(6) yes . .
F3 C10 1.383(7) yes . .
F4 C10 1.390(5) yes . .
F5 C27 1.375(6) yes . .
F6 C27 1.388(6) yes . .
F7 C30 1.367(8) yes . .
F8 C30 1.380(6) yes . .
O1 C2 1.348(5) yes . .
O1 C14 1.454(6) yes . .
O2 C2 1.200(6) yes . .
O21 C22 1.337(6) yes . .
O21 C34 1.470(7) yes . .
O22 C22 1.205(6) yes . .
C2 C3 1.501(7) yes . .
C3 C4 1.531(7) yes . .
C4 C5 1.521(7) yes . .
C5 C6 1.528(7) yes . .
C6 C7 1.500(8) yes . .
C7 C8 1.509(7) yes . .
C8 C9 1.536(6) yes . .
C9 C10 1.509(7) yes . .
C10 C11 1.495(8) yes . .
C11 C12 1.529(8) yes . .
C12 C13 1.528(7) yes . .
C13 C14 1.528(7) yes . .
C13 C15 1.520(7) yes . .
C22 C23 1.498(8) yes . .
C23 C24 1.519(8) yes . .
C24 C25 1.516(7) yes . .
C25 C26 1.534(7) yes . .
C26 C27 1.500(8) yes . .
C27 C28 1.513(8) yes . .
C28 C29 1.529(7) yes . .
C29 C30 1.498(8) yes . .
C30 C31 1.512(9) yes . .
C31 C32 1.541(9) yes . .
C32 C33 1.538(9) yes . .
C33 C34 1.470(8) yes . .
C33 C35 1.541(10) yes . .
C3 H3A 0.990 no . .
C3 H3B 0.990 no . .
C4 H4A 0.990 no . .
C4 H4B 0.990 no . .
C5 H5A 0.990 no . .
C5 H5B 0.990 no . .
C6 H6A 0.990 no . .
C6 H6B 0.990 no . .
C8 H8A 0.990 no . .
C8 H8B 0.990 no . .
C9 H9A 0.990 no . .
C9 H9B 0.990 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13 1.000 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .
C23 H23A 0.990 no . .
C23 H23B 0.990 no . .
C24 H24A 0.990 no . .
C24 H24B 0.990 no . .
C25 H25A 0.990 no . .
C25 H25B 0.990 no . .
C26 H26A 0.990 no . .
C26 H26B 0.990 no . .
C28 H28A 0.990 no . .
C28 H28B 0.990 no . .
C29 H29A 0.990 no . .
C29 H29B 0.990 no . .
C31 H31A 0.990 no . .
C31 H31B 0.990 no . .
C32 H32A 0.990 no . .
C32 H32B 0.990 no . .
C33 H33 1.000 no . .
C34 H34A 0.990 no . .
C34 H34B 0.990 no . .
C35 H35A 0.980 no . .
C35 H35B 0.980 no . .
C35 H35C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 O1 C14 116.7(4) yes . . .
C22 O21 C34 113.6(4) yes . . .
O1 C2 O2 123.7(5) yes . . .
O1 C2 C3 111.2(4) yes . . .
O2 C2 C3 125.1(4) yes . . .
C2 C3 C4 114.4(4) yes . . .
C3 C4 C5 112.4(4) yes . . .
C4 C5 C6 111.5(4) yes . . .
C5 C6 C7 113.1(4) yes . . .
F1 C7 F2 104.2(4) yes . . .
F1 C7 C6 109.2(4) yes . . .
F1 C7 C8 107.8(4) yes . . .
F2 C7 C6 107.9(4) yes . . .
F2 C7 C8 108.4(4) yes . . .
C6 C7 C8 118.4(5) yes . . .
C7 C8 C9 112.3(4) yes . . .
C8 C9 C10 113.3(4) yes . . .
F3 C10 F4 104.4(4) yes . . .
F3 C10 C9 109.1(5) yes . . .
F3 C10 C11 108.6(4) yes . . .
F4 C10 C9 106.3(4) yes . . .
F4 C10 C11 108.4(4) yes . . .
C9 C10 C11 119.1(5) yes . . .
C10 C11 C12 114.0(5) yes . . .
C11 C12 C13 113.8(4) yes . . .
C12 C13 C14 111.1(4) yes . . .
C12 C13 C15 112.8(4) yes . . .
C14 C13 C15 108.5(4) yes . . .
O1 C14 C13 112.7(4) yes . . .
O21 C22 O22 122.2(5) yes . . .
O21 C22 C23 112.6(5) yes . . .
O22 C22 C23 125.2(5) yes . . .
C22 C23 C24 114.0(5) yes . . .
C23 C24 C25 112.6(4) yes . . .
C24 C25 C26 112.2(4) yes . . .
C25 C26 C27 113.5(4) yes . . .
F5 C27 F6 105.0(4) yes . . .
F5 C27 C26 109.0(4) yes . . .
F5 C27 C28 107.3(4) yes . . .
F6 C27 C26 107.9(4) yes . . .
F6 C27 C28 108.1(4) yes . . .
C26 C27 C28 118.7(5) yes . . .
C27 C28 C29 112.9(4) yes . . .
C28 C29 C30 113.5(5) yes . . .
F7 C30 F8 103.5(5) yes . . .
F7 C30 C29 109.5(5) yes . . .
F7 C30 C31 108.5(5) yes . . .
F8 C30 C29 107.4(5) yes . . .
F8 C30 C31 108.7(5) yes . . .
C29 C30 C31 118.3(5) yes . . .
C30 C31 C32 111.7(5) yes . . .
C31 C32 C33 117.6(6) yes . . .
C32 C33 C34 113.2(5) yes . . .
C32 C33 C35 112.7(6) yes . . .
C34 C33 C35 107.8(6) yes . . .
O21 C34 C33 108.2(5) yes . . .
C2 C3 H3A 108.661 no . . .
C2 C3 H3B 108.664 no . . .
C4 C3 H3A 108.665 no . . .
C4 C3 H3B 108.660 no . . .
H3A C3 H3B 107.596 no . . .
C3 C4 H4A 109.105 no . . .
C3 C4 H4B 109.107 no . . .
C5 C4 H4A 109.112 no . . .
C5 C4 H4B 109.115 no . . .
H4A C4 H4B 107.847 no . . .
C4 C5 H5A 109.332 no . . .
C4 C5 H5B 109.331 no . . .
C6 C5 H5A 109.328 no . . .
C6 C5 H5B 109.333 no . . .
H5A C5 H5B 107.983 no . . .
C5 C6 H6A 108.957 no . . .
C5 C6 H6B 108.947 no . . .
C7 C6 H6A 108.948 no . . .
C7 C6 H6B 108.946 no . . .
H6A C6 H6B 107.763 no . . .
C7 C8 H8A 109.138 no . . .
C7 C8 H8B 109.146 no . . .
C9 C8 H8A 109.131 no . . .
C9 C8 H8B 109.135 no . . .
H8A C8 H8B 107.859 no . . .
C8 C9 H9A 108.910 no . . .
C8 C9 H9B 108.907 no . . .
C10 C9 H9A 108.919 no . . .
C10 C9 H9B 108.910 no . . .
H9A C9 H9B 107.741 no . . .
C10 C11 H11A 108.767 no . . .
C10 C11 H11B 108.762 no . . .
C12 C11 H11A 108.760 no . . .
C12 C11 H11B 108.757 no . . .
H11A C11 H11B 107.654 no . . .
C11 C12 H12A 108.793 no . . .
C11 C12 H12B 108.801 no . . .
C13 C12 H12A 108.796 no . . .
C13 C12 H12B 108.796 no . . .
H12A C12 H12B 107.672 no . . .
C12 C13 H13 108.092 no . . .
C14 C13 H13 108.101 no . . .
C15 C13 H13 108.101 no . . .
O1 C14 H14A 109.042 no . . .
O1 C14 H14B 109.045 no . . .
C13 C14 H14A 109.050 no . . .
C13 C14 H14B 109.055 no . . .
H14A C14 H14B 107.808 no . . .
C13 C15 H15A 109.479 no . . .
C13 C15 H15B 109.470 no . . .
C13 C15 H15C 109.475 no . . .
H15A C15 H15B 109.463 no . . .
H15A C15 H15C 109.470 no . . .
H15B C15 H15C 109.471 no . . .
C22 C23 H23A 108.758 no . . .
C22 C23 H23B 108.757 no . . .
C24 C23 H23A 108.756 no . . .
C24 C23 H23B 108.754 no . . .
H23A C23 H23B 107.648 no . . .
C23 C24 H24A 109.079 no . . .
C23 C24 H24B 109.078 no . . .
C25 C24 H24A 109.072 no . . .
C25 C24 H24B 109.073 no . . .
H24A C24 H24B 107.822 no . . .
C24 C25 H25A 109.171 no . . .
C24 C25 H25B 109.170 no . . .
C26 C25 H25A 109.173 no . . .
C26 C25 H25B 109.166 no . . .
H25A C25 H25B 107.883 no . . .
C25 C26 H26A 108.877 no . . .
C25 C26 H26B 108.886 no . . .
C27 C26 H26A 108.876 no . . .
C27 C26 H26B 108.878 no . . .
H26A C26 H26B 107.719 no . . .
C27 C28 H28A 108.996 no . . .
C27 C28 H28B 108.985 no . . .
C29 C28 H28A 109.005 no . . .
C29 C28 H28B 109.005 no . . .
H28A C28 H28B 107.790 no . . .
C28 C29 H29A 108.874 no . . .
C28 C29 H29B 108.865 no . . .
C30 C29 H29A 108.862 no . . .
C30 C29 H29B 108.862 no . . .
H29A C29 H29B 107.708 no . . .
C30 C31 H31A 109.281 no . . .
C30 C31 H31B 109.279 no . . .
C32 C31 H31A 109.280 no . . .
C32 C31 H31B 109.279 no . . .
H31A C31 H31B 107.943 no . . .
C31 C32 H32A 107.903 no . . .
C31 C32 H32B 107.911 no . . .
C33 C32 H32A 107.906 no . . .
C33 C32 H32B 107.906 no . . .
H32A C32 H32B 107.192 no . . .
C32 C33 H33 107.622 no . . .
C34 C33 H33 107.614 no . . .
C35 C33 H33 107.625 no . . .
O21 C34 H34A 110.070 no . . .
O21 C34 H34B 110.066 no . . .
C33 C34 H34A 110.069 no . . .
C33 C34 H34B 110.063 no . . .
H34A C34 H34B 108.407 no . . .
C33 C35 H35A 109.475 no . . .
C33 C35 H35B 109.473 no . . .
C33 C35 H35C 109.470 no . . .
H35A C35 H35B 109.468 no . . .
H35A C35 H35C 109.471 no . . .
H35B C35 H35C 109.470 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 O1 C14 C13 82.4(5) no . . . .
C14 O1 C2 O2 -1.2(7) no . . . .
C14 O1 C2 C3 178.5(4) no . . . .
C22 O21 C34 C33 -175.5(4) no . . . .
C34 O21 C22 O22 -6.3(7) no . . . .
C34 O21 C22 C23 173.2(4) no . . . .
O1 C2 C3 C4 50.1(6) no . . . .
O2 C2 C3 C4 -130.2(5) no . . . .
C2 C3 C4 C5 61.2(5) no . . . .
C3 C4 C5 C6 -177.3(4) no . . . .
C4 C5 C6 C7 169.7(4) no . . . .
C5 C6 C7 F1 63.5(5) no . . . .
C5 C6 C7 F2 176.2(4) no . . . .
C5 C6 C7 C8 -60.2(5) no . . . .
F1 C7 C8 C9 174.0(4) no . . . .
F2 C7 C8 C9 61.7(5) no . . . .
C6 C7 C8 C9 -61.6(6) no . . . .
C7 C8 C9 C10 168.4(4) no . . . .
C8 C9 C10 F3 66.1(5) no . . . .
C8 C9 C10 F4 178.2(4) no . . . .
C8 C9 C10 C11 -59.2(6) no . . . .
F3 C10 C11 C12 178.1(3) no . . . .
F4 C10 C11 C12 65.3(5) no . . . .
C9 C10 C11 C12 -56.3(6) no . . . .
C10 C11 C12 C13 169.7(4) no . . . .
C11 C12 C13 C14 -171.8(4) no . . . .
C11 C12 C13 C15 66.1(5) no . . . .
C12 C13 C14 O1 56.6(5) no . . . .
C15 C13 C14 O1 -178.9(4) no . . . .
O21 C22 C23 C24 -43.1(6) no . . . .
O22 C22 C23 C24 136.4(5) no . . . .
C22 C23 C24 C25 -56.3(5) no . . . .
C23 C24 C25 C26 178.8(4) no . . . .
C24 C25 C26 C27 -168.2(4) no . . . .
C25 C26 C27 F5 -63.0(6) no . . . .
C25 C26 C27 F6 -176.5(4) no . . . .
C25 C26 C27 C28 60.2(5) no . . . .
F5 C27 C28 C29 -174.9(4) no . . . .
F6 C27 C28 C29 -62.1(5) no . . . .
C26 C27 C28 C29 61.1(6) no . . . .
C27 C28 C29 C30 -165.2(4) no . . . .
C28 C29 C30 F7 -58.0(6) no . . . .
C28 C29 C30 F8 -169.7(5) no . . . .
C28 C29 C30 C31 67.0(6) no . . . .
F7 C30 C31 C32 -168.2(4) no . . . .
F8 C30 C31 C32 -56.3(6) no . . . .
C29 C30 C31 C32 66.4(6) no . . . .
C30 C31 C32 C33 179.3(4) no . . . .
C31 C32 C33 C34 70.6(7) no . . . .
C31 C32 C33 C35 -52.1(6) no . . . .
C32 C33 C34 O21 62.3(7) no . . . .
C35 C33 C34 O21 -172.3(5) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C5 2.926(6) no . .
F2 C9 2.899(6) no . .
F3 C8 2.968(6) no . .
F4 C12 2.946(6) no . .
F5 C25 2.925(6) no . .
F6 C29 2.904(7) no . .
F7 C28 2.878(7) no . .
F8 C32 2.837(7) no . .
O1 C4 2.853(6) no . .
O1 C5 3.436(6) no . .
O1 C12 2.948(6) no . .
O2 C4 3.556(6) no . .
O2 C13 3.222(6) no . .
O2 C14 2.685(6) no . .
O21 C24 2.805(6) no . .
O21 C25 3.236(7) no . .
O21 C32 2.921(7) no . .
O22 C24 3.574(7) no . .
O22 C34 2.592(7) no . .
C2 C5 3.075(7) no . .
C2 C13 3.164(7) no . .
C5 C8 3.135(8) no . .
C6 C9 3.138(7) no . .
C8 C11 3.145(7) no . .
C9 C12 3.124(8) no . .
C11 C15 3.133(8) no . .
C22 C25 3.009(8) no . .
C22 C33 3.597(8) no . .
C25 C28 3.152(8) no . .
C26 C29 3.151(8) no . .
C28 C31 3.202(8) no . .
C29 C32 3.173(9) no . .
C31 C34 3.236(9) no . .
C31 C35 3.100(10) no . .
F1 F7 3.273(5) no . 2_646
F1 C28 3.401(6) no . 2_646
F1 C35 3.398(8) no . .
F2 F6 3.463(4) no . 2_746
F2 O1 3.222(5) no . 1_545
F2 O2 3.586(5) no . 1_545
F2 C2 3.106(6) no . 1_545
F2 C3 3.249(6) no . 1_545
F2 C29 3.321(6) no . 2_746
F3 F5 3.526(4) no . 2_646
F3 C14 3.562(6) no . 1_545
F3 C23 3.526(6) no . 1_556
F3 C24 3.508(6) no . 1_556
F4 C24 3.475(6) no . 1_556
F5 F3 3.526(4) no . 2_656
F5 O22 3.415(6) no . 1_565
F5 C8 3.432(6) no . 2_656
F5 C15 3.339(6) no . 1_554
F6 F2 3.463(4) no . 2_756
F6 O21 3.353(5) no . 1_565
F6 O22 3.412(5) no . 1_565
F6 C9 3.291(6) no . 2_756
F6 C22 3.069(6) no . 1_565
F6 C23 3.264(6) no . 1_565
F7 F1 3.273(5) no . 2_656
F8 C4 3.373(6) no . .
F8 C32 3.569(7) no . 2_756
F8 C33 3.315(7) no . 2_756
F8 C35 3.575(9) no . 2_756
O1 F2 3.222(5) no . 1_565
O1 C24 3.477(6) no . 2_756
O2 F2 3.586(5) no . 1_565
O2 O22 3.583(6) no . 2_656
O2 C25 3.450(7) no . 2_656
O2 C28 3.317(6) no . 2_656
O21 F6 3.353(5) no . 1_545
O22 F5 3.415(6) no . 1_545
O22 F6 3.412(5) no . 1_545
O22 O2 3.583(6) no . 2_646
O22 C5 3.564(6) no . 2_646
O22 C8 3.332(7) no . 2_646
O22 C11 3.416(6) no . 2_646
O22 C13 3.507(6) no . 2_646
C2 F2 3.106(6) no . 1_565
C3 F2 3.249(6) no . 1_565
C4 F8 3.373(6) no . .
C5 O22 3.564(6) no . 2_656
C8 F5 3.432(6) no . 2_646
C8 O22 3.332(7) no . 2_656
C9 F6 3.291(6) no . 2_746
C11 O22 3.416(6) no . 2_656
C13 O22 3.507(6) no . 2_656
C14 F3 3.562(6) no . 1_565
C15 F5 3.339(6) no . 1_556
C22 F6 3.069(6) no . 1_545
C23 F3 3.526(6) no . 1_554
C23 F6 3.264(6) no . 1_545
C24 F3 3.508(6) no . 1_554
C24 F4 3.475(6) no . 1_554
C24 O1 3.477(6) no . 2_746
C25 O2 3.450(7) no . 2_646
C28 F1 3.401(6) no . 2_656
C28 O2 3.317(6) no . 2_646
C29 F2 3.321(6) no . 2_756
C32 F8 3.569(7) no . 2_746
C33 F8 3.315(7) no . 2_746
C35 F1 3.398(8) no . .
C35 F8 3.575(9) no . 2_746
F1 H5A 2.7066 no . .
F1 H5B 3.1355 no . .
F1 H6A 2.5387 no . .
F1 H6B 3.1887 no . .
F1 H8A 2.4880 no . .
F1 H8B 2.5751 no . .
F2 H6A 2.5040 no . .
F2 H6B 2.5589 no . .
F2 H8A 2.5563 no . .
F2 H8B 3.2033 no . .
F2 H9A 2.6694 no . .
F2 H9B 3.0768 no . .
F3 H8A 2.7576 no . .
F3 H8B 3.1717 no . .
F3 H9A 2.5298 no . .
F3 H9B 3.1968 no . .
F3 H11A 2.5144 no . .
F3 H11B 2.5413 no . .
F4 H9A 2.4928 no . .
F4 H9B 2.5197 no . .
F4 H11A 2.5128 no . .
F4 H11B 3.1848 no . .
F4 H12A 2.7150 no . .
F4 H12B 3.1620 no . .
F5 H25A 3.1127 no . .
F5 H25B 2.7184 no . .
F5 H26A 3.1848 no . .
F5 H26B 2.5378 no . .
F5 H28A 2.5586 no . .
F5 H28B 2.4844 no . .
F6 H26A 2.5528 no . .
F6 H26B 2.5018 no . .
F6 H28A 3.1967 no . .
F6 H28B 2.5469 no . .
F6 H29A 3.0461 no . .
F6 H29B 2.7081 no . .
F7 H28A 2.9969 no . .
F7 H28B 2.7005 no . .
F7 H29A 3.1820 no . .
F7 H29B 2.5753 no . .
F7 H31A 2.6302 no . .
F7 H31B 2.4636 no . .
F8 H29A 2.5878 no . .
F8 H29B 2.4382 no . .
F8 H31A 3.1978 no . .
F8 H31B 2.5969 no . .
F8 H32A 3.1132 no . .
F8 H32B 2.4784 no . .
O1 H3A 2.6498 no . .
O1 H3B 3.1788 no . .
O1 H4B 2.5688 no . .
O1 H5B 2.9684 no . .
O1 H12A 3.3129 no . .
O1 H12B 2.5333 no . .
O1 H13 2.6949 no . .
O2 H3A 2.9504 no . .
O2 H3B 2.5120 no . .
O2 H5B 3.2877 no . .
O2 H13 2.7291 no . .
O2 H14A 2.4262 no . .
O21 H23A 3.1729 no . .
O21 H23B 2.7154 no . .
O21 H24A 2.5785 no . .
O21 H25A 2.6951 no . .
O21 H31A 3.5358 no . .
O21 H32A 2.5194 no . .
O21 H33 2.5234 no . .
O22 H23A 2.5237 no . .
O22 H23B 2.9226 no . .
O22 H25A 3.3395 no . .
O22 H34A 2.5729 no . .
O22 H34B 2.5347 no . .
C2 H4A 3.3797 no . .
C2 H4B 2.7545 no . .
C2 H5A 3.4002 no . .
C2 H5B 2.7175 no . .
C2 H12B 3.3354 no . .
C2 H13 2.9333 no . .
C2 H14A 2.4999 no . .
C2 H14B 3.1732 no . .
C3 H5A 2.7461 no . .
C3 H5B 2.7063 no . .
C4 H6A 2.7780 no . .
C4 H6B 2.6279 no . .
C5 H3A 3.3738 no . .
C5 H3B 2.7288 no . .
C5 H8B 2.8298 no . .
C5 H9B 3.3612 no . .
C5 H12B 3.2638 no . .
C6 H4A 2.7217 no . .
C6 H4B 2.6815 no . .
C6 H8A 3.4016 no . .
C6 H8B 2.8031 no . .
C6 H9A 3.5455 no . .
C6 H9B 2.7323 no . .
C7 H5A 2.8009 no . .
C7 H5B 2.6558 no . .
C7 H9A 2.8011 no . .
C7 H9B 2.6367 no . .
C8 H5A 3.5329 no . .
C8 H5B 2.7441 no . .
C8 H6A 3.4019 no . .
C8 H6B 2.8084 no . .
C8 H11B 2.8784 no . .
C8 H12B 3.2456 no . .
C9 H5B 3.3639 no . .
C9 H6B 2.8367 no . .
C9 H11A 3.4014 no . .
C9 H11B 2.8398 no . .
C9 H12A 3.4933 no . .
C9 H12B 2.7236 no . .
C10 H8A 2.8220 no . .
C10 H8B 2.6599 no . .
C10 H12A 2.8015 no . .
C10 H12B 2.6582 no . .
C11 H8A 3.5449 no . .
C11 H8B 2.7496 no . .
C11 H9A 3.4003 no . .
C11 H9B 2.8234 no . .
C11 H13 2.7024 no . .
C11 H15A 3.4687 no . .
C11 H15B 2.8057 no . .
C12 H5B 3.3049 no . .
C12 H8B 3.2662 no . .
C12 H9B 2.8387 no . .
C12 H14A 3.3673 no . .
C12 H14B 2.7443 no . .
C12 H15A 2.7400 no . .
C12 H15B 2.7324 no . .
C12 H15C 3.3750 no . .
C13 H11A 2.8211 no . .
C13 H11B 2.6754 no . .
C14 H12A 2.7568 no . .
C14 H12B 2.6356 no . .
C14 H15A 2.6793 no . .
C14 H15B 3.3270 no . .
C14 H15C 2.6336 no . .
C15 H11A 2.8765 no . .
C15 H11B 3.3262 no . .
C15 H12A 2.6988 no . .
C15 H12B 3.3737 no . .
C15 H14A 2.6377 no . .
C15 H14B 2.6551 no . .
C22 H24A 2.7703 no . .
C22 H24B 3.3645 no . .
C22 H25A 2.6537 no . .
C22 H25B 3.2920 no . .
C22 H34A 2.6219 no . .
C22 H34B 2.5629 no . .
C23 H25A 2.7055 no . .
C23 H25B 2.7225 no . .
C24 H26A 2.6337 no . .
C24 H26B 2.8032 no . .
C25 H23A 2.7557 no . .
C25 H23B 3.3641 no . .
C25 H28A 2.8514 no . .
C25 H29A 3.3776 no . .
C25 H32A 3.5786 no . .
C26 H24A 2.7054 no . .
C26 H24B 2.7225 no . .
C26 H28A 2.8136 no . .
C26 H28B 3.4062 no . .
C26 H29A 2.7312 no . .
C26 H29B 3.5925 no . .
C27 H25A 2.6549 no . .
C27 H25B 2.8200 no . .
C27 H29A 2.6228 no . .
C27 H29B 2.8316 no . .
C28 H25A 2.7537 no . .
C28 H25B 3.5643 no . .
C28 H26A 2.8164 no . .
C28 H26B 3.4079 no . .
C28 H31A 2.8815 no . .
C28 H32A 3.5746 no . .
C29 H25A 3.3740 no . .
C29 H26A 2.8550 no . .
C29 H31A 2.7716 no . .
C29 H31B 3.3991 no . .
C29 H32A 2.8319 no . .
C29 H32B 3.4324 no . .
C30 H28A 2.6281 no . .
C30 H28B 2.8340 no . .
C30 H32A 2.6939 no . .
C30 H32B 2.6833 no . .
C31 H28A 2.8053 no . .
C31 H29A 2.7611 no . .
C31 H29B 3.3972 no . .
C31 H33 3.4450 no . .
C31 H34B 2.9195 no . .
C31 H35B 2.8188 no . .
C31 H35C 3.2786 no . .
C32 H29A 2.8325 no . .
C32 H34A 3.3653 no . .
C32 H34B 2.7025 no . .
C32 H35A 3.3972 no . .
C32 H35B 2.7945 no . .
C32 H35C 2.7265 no . .
C33 H31A 2.8466 no . .
C33 H31B 2.8369 no . .
C34 H25A 3.4777 no . .
C34 H31A 2.9697 no . .
C34 H31B 3.5802 no . .
C34 H32A 2.6450 no . .
C34 H32B 3.3256 no . .
C34 H35A 2.6189 no . .
C34 H35B 2.6323 no . .
C34 H35C 3.2822 no . .
C35 H31A 3.3738 no . .
C35 H31B 2.7743 no . .
C35 H32A 3.3937 no . .
C35 H32B 2.8179 no . .
C35 H34A 2.5588 no . .
C35 H34B 2.6787 no . .
H3A H4A 2.3427 no . .
H3A H4B 2.3741 no . .
H3B H4A 2.3695 no . .
H3B H4B 2.8678 no . .
H3B H5A 2.5683 no . .
H3B H5B 2.9860 no . .
H4A H5A 2.3619 no . .
H4A H5B 2.8658 no . .
H4A H6A 2.6149 no . .
H4A H6B 2.8893 no . .
H4B H5A 2.8658 no . .
H4B H5B 2.3930 no . .
H4B H6A 3.0578 no . .
H4B H6B 2.4111 no . .
H4B H12B 3.1719 no . .
H5A H6A 2.3266 no . .
H5A H6B 2.8651 no . .
H5A H8B 3.1631 no . .
H5B H6A 2.8657 no . .
H5B H6B 2.4429 no . .
H5B H8B 2.2009 no . .
H5B H9B 3.0031 no . .
H5B H11B 3.4719 no . .
H5B H12B 2.5059 no . .
H5B H13 3.2689 no . .
H6B H8B 3.1235 no . .
H6B H9A 3.1835 no . .
H6B H9B 2.1895 no . .
H6B H12B 3.2959 no . .
H8A H9A 2.3256 no . .
H8A H9B 2.8682 no . .
H8A H11B 3.1847 no . .
H8B H9A 2.8685 no . .
H8B H9B 2.4559 no . .
H8B H11B 2.2591 no . .
H8B H12B 2.8389 no . .
H9B H11B 3.1960 no . .
H9B H12A 3.1098 no . .
H9B H12B 2.2221 no . .
H11A H12A 2.3206 no . .
H11A H12B 2.8601 no . .
H11A H13 3.0719 no . .
H11A H15A 3.1193 no . .
H11A H15B 2.3329 no . .
H11B H12A 2.8600 no . .
H11B H12B 2.4387 no . .
H11B H13 2.4380 no . .
H11B H15B 2.9251 no . .
H12A H13 2.8654 no . .
H12A H14B 2.6137 no . .
H12A H15A 2.5316 no . .
H12A H15B 2.9697 no . .
H12A H15C 3.5952 no . .
H12B H13 2.4027 no . .
H12B H14A 3.5436 no . .
H12B H14B 2.9411 no . .
H12B H15A 3.5976 no . .
H13 H14A 2.3556 no . .
H13 H14B 2.8689 no . .
H13 H15A 2.8583 no . .
H13 H15B 2.3526 no . .
H13 H15C 2.3527 no . .
H14A H15A 2.9462 no . .
H14A H15B 3.5274 no . .
H14A H15C 2.4153 no . .
H14B H15A 2.4832 no . .
H14B H15B 3.5623 no . .
H14B H15C 2.9042 no . .
H23A H24A 2.8579 no . .
H23A H24B 2.3333 no . .
H23A H25A 3.0464 no . .
H23A H25B 2.5843 no . .
H23B H24A 2.3365 no . .
H23B H24B 2.3605 no . .
H23B H25A 3.5934 no . .
H24A H25A 2.3783 no . .
H24A H25B 2.8610 no . .
H24A H26A 2.4336 no . .
H24A H26B 3.1043 no . .
H24A H32A 3.1352 no . .
H24B H25A 2.8609 no . .
H24B H25B 2.3648 no . .
H24B H26A 2.8695 no . .
H24B H26B 2.6331 no . .
H25A H26A 2.4559 no . .
H25A H26B 2.8670 no . .
H25A H28A 2.2142 no . .
H25A H29A 3.0332 no . .
H25A H31A 3.1052 no . .
H25A H32A 2.9338 no . .
H25A H34B 3.2278 no . .
H25B H26A 2.8663 no . .
H25B H26B 2.3225 no . .
H25B H28A 3.1987 no . .
H26A H28A 3.1372 no . .
H26A H29A 2.1908 no . .
H26A H29B 3.2390 no . .
H26A H32A 3.3610 no . .
H28A H29A 2.4677 no . .
H28A H29B 2.8573 no . .
H28A H31A 2.2226 no . .
H28A H32A 3.2940 no . .
H28B H29A 2.8570 no . .
H28B H29B 2.3003 no . .
H28B H31A 3.3532 no . .
H29A H31A 2.9990 no . .
H29A H32A 2.2465 no . .
H29A H32B 3.0676 no . .
H31A H32A 2.3805 no . .
H31A H32B 2.8702 no . .
H31A H34B 2.4010 no . .
H31A H35B 2.9397 no . .
H31B H32A 2.8705 no . .
H31B H32B 2.3890 no . .
H31B H34B 3.2321 no . .
H31B H35B 2.3329 no . .
H31B H35C 2.8225 no . .
H32A H33 2.3876 no . .
H32A H34A 3.5691 no . .
H32A H34B 2.8933 no . .
H32B H33 2.2819 no . .
H32B H35B 3.1973 no . .
H32B H35C 2.6295 no . .
H33 H34A 2.3355 no . .
H33 H34B 2.8296 no . .
H33 H35A 2.3466 no . .
H33 H35B 2.8690 no . .
H33 H35C 2.3833 no . .
H34A H35A 2.3574 no . .
H34A H35B 2.8283 no . .
H34A H35C 3.4652 no . .
H34B H35A 2.9841 no . .
H34B H35B 2.4999 no . .
H34B H35C 3.5628 no . .
F1 H3A 3.5666 no . 1_545
F1 H28A 3.1999 no . 2_646
F1 H28B 2.6952 no . 2_646
F1 H31B 3.5768 no . .
F1 H34A 3.4529 no . 2_656
F1 H35B 3.0735 no . .
F1 H35C 2.8769 no . .
F2 H3A 2.5453 no . 1_545
F2 H26A 2.8115 no . 2_746
F2 H29A 2.7262 no . 2_746
F2 H29B 2.9924 no . 2_746
F2 H35C 2.9539 no . .
F3 H14A 2.8938 no . 1_545
F3 H14B 3.3092 no . 1_545
F3 H15B 3.2810 no . 2_647
F3 H15C 3.3629 no . 1_545
F3 H23A 2.8845 no . 1_556
F3 H24B 2.8288 no . 1_556
F3 H25B 3.5319 no . 1_556
F4 H12A 2.8312 no . 2_747
F4 H14B 2.8077 no . 2_747
F4 H15A 2.8985 no . 2_747
F4 H24B 2.4986 no . 1_556
F4 H26B 3.4133 no . 1_556
F5 H8A 2.7589 no . 2_656
F5 H8B 3.1845 no . 2_656
F5 H11B 3.4806 no . 2_656
F5 H14A 3.4892 no . 2_646
F5 H15A 3.2033 no . 1_554
F5 H15B 2.6830 no . 1_554
F6 H6B 2.8575 no . 2_756
F6 H9A 2.9018 no . 2_756
F6 H9B 2.7521 no . 2_756
F6 H15A 3.3915 no . 1_554
F6 H23B 2.5935 no . 1_565
F7 H3B 3.2705 no . .
F7 H4A 3.1163 no . .
F7 H5A 3.4883 no . .
F7 H34A 3.3646 no . 1_565
F7 H35A 3.1054 no . 1_565
F7 H35B 3.0905 no . 2_656
F8 H4A 2.4135 no . .
F8 H6A 3.2378 no . .
F8 H32B 2.9160 no . 2_756
F8 H33 2.6186 no . 2_756
F8 H35C 3.0508 no . 2_756
O1 H8A 3.4601 no . 1_565
O1 H24A 2.7145 no . 2_756
O1 H24B 3.3764 no . 2_756
O1 H26A 3.0286 no . 2_756
O2 H8A 3.0547 no . 1_565
O2 H25A 2.6602 no . 2_656
O2 H25B 3.3688 no . 2_656
O2 H28A 2.3514 no . 2_656
O2 H31A 2.6608 no . 2_656
O2 H34B 2.9254 no . 2_656
O21 H4B 2.9800 no . 2_746
O21 H6B 3.3365 no . 2_746
O22 H5A 3.5184 no . 2_646
O22 H5B 2.7462 no . 2_646
O22 H8B 2.3571 no . 2_646
O22 H11B 2.5275 no . 2_646
O22 H12B 3.5831 no . 2_646
O22 H13 2.6212 no . 2_646
O22 H28B 3.1744 no . 1_545
C2 H8A 3.3470 no . 1_565
C2 H28A 3.4428 no . 2_656
C2 H31A 3.4213 no . 2_656
C2 H34B 3.3734 no . 2_656
C3 H31A 3.5574 no . 2_656
C3 H32A 3.5952 no . 2_756
C3 H34B 3.5047 no . 2_656
C3 H35A 3.2934 no . 1_565
C3 H35C 3.5489 no . 1_565
C4 H24A 3.3548 no . 2_756
C4 H32A 3.0879 no . 2_756
C4 H32B 3.4280 no . 2_756
C4 H33 3.2288 no . 2_756
C5 H34B 3.2522 no . 2_656
C6 H29B 3.3132 no . 2_746
C6 H35C 3.5359 no . .
C7 H35C 3.3393 no . .
C8 H14A 3.1925 no . 1_545
C8 H28B 3.3864 no . 2_646
C9 H14A 3.3837 no . 1_545
C9 H26B 3.5726 no . 2_746
C10 H24B 3.1710 no . 1_556
C11 H15C 3.5811 no . 2_647
C11 H25B 3.5736 no . 1_556
C11 H26B 3.4701 no . 1_556
C12 H24B 3.4145 no . 2_756
C13 H23A 3.5984 no . 2_656
C13 H25B 3.4428 no . 2_656
C14 H8A 3.1959 no . 1_565
C14 H9A 3.2729 no . 1_565
C14 H24A 3.4444 no . 2_756
C14 H24B 3.4306 no . 2_756
C14 H26A 3.5772 no . 2_756
C15 H23A 3.5646 no . 1_566
C15 H25B 3.3257 no . 2_656
C22 H8B 3.5209 no . 2_646
C22 H11B 3.3839 no . 2_646
C22 H13 3.0988 no . 2_646
C22 H28B 3.5433 no . 1_545
C23 H13 3.3579 no . 2_646
C23 H15A 3.5094 no . 1_544
C24 H4B 3.3643 no . 2_746
C24 H12A 3.4713 no . 2_746
C24 H12B 3.5014 no . 2_746
C24 H14B 3.4023 no . 2_746
C25 H11A 3.2693 no . 1_554
C25 H13 3.4106 no . 2_646
C26 H9A 3.1018 no . 2_756
C26 H11A 3.3354 no . 1_554
C26 H14B 3.5462 no . 2_746
C28 H8A 3.4059 no . 2_656
C28 H34A 3.4405 no . 1_565
C30 H4A 3.3416 no . .
C31 H3B 3.5835 no . 2_646
C32 H4A 3.0732 no . 2_746
C32 H4B 3.3274 no . 2_746
C33 H4A 3.2471 no . 2_746
C33 H4B 3.5507 no . 2_746
C34 H5A 3.2601 no . 2_646
C34 H28B 3.4620 no . 1_545
C35 H3A 3.2692 no . 1_545
C35 H3B 3.4889 no . 1_545
H3A F1 3.5666 no . 1_565
H3A F2 2.5453 no . 1_565
H3A C35 3.2692 no . 1_565
H3A H26A 3.5677 no . 2_756
H3A H29A 3.0519 no . 2_756
H3A H32A 3.0650 no . 2_756
H3A H32B 3.2900 no . 2_756
H3A H35A 2.8732 no . 1_565
H3A H35C 2.7818 no . 1_565
H3B F7 3.2705 no . .
H3B C31 3.5835 no . 2_656
H3B C35 3.4889 no . 1_565
H3B H31A 2.8309 no . 2_656
H3B H31B 3.4297 no . 2_656
H3B H34B 2.9476 no . 2_656
H3B H35A 2.7847 no . 1_565
H3B H35B 3.3362 no . 2_656
H3B H35C 3.4192 no . 1_565
H4A F7 3.1163 no . .
H4A F8 2.4135 no . .
H4A C30 3.3416 no . .
H4A C32 3.0732 no . 2_756
H4A C33 3.2471 no . 2_756
H4A H32A 2.7914 no . 2_756
H4A H32B 2.7278 no . 2_756
H4A H33 2.5431 no . 2_756
H4B O21 2.9800 no . 2_756
H4B C24 3.3643 no . 2_756
H4B C32 3.3274 no . 2_756
H4B C33 3.5507 no . 2_756
H4B H24A 2.3983 no . 2_756
H4B H32A 2.6214 no . 2_756
H4B H32B 3.4053 no . 2_756
H4B H33 3.0420 no . 2_756
H5A F7 3.4883 no . .
H5A O22 3.5184 no . 2_656
H5A C34 3.2601 no . 2_656
H5A H31B 3.0416 no . .
H5A H34A 2.9554 no . 2_656
H5A H34B 2.6586 no . 2_656
H5A H35B 3.3147 no . 2_656
H5B O22 2.7462 no . 2_656
H5B H34A 3.4764 no . 2_656
H5B H34B 2.9914 no . 2_656
H6A F8 3.2378 no . .
H6A H29B 2.8820 no . 2_746
H6A H31B 2.9393 no . .
H6A H32B 3.1543 no . .
H6A H33 3.1976 no . 2_756
H6A H35C 2.8351 no . .
H6B F6 2.8575 no . 2_746
H6B O21 3.3365 no . 2_756
H6B H23B 3.4821 no . 2_756
H6B H29B 2.9627 no . 2_746
H6B H33 3.3728 no . 2_756
H8A F5 2.7589 no . 2_646
H8A O1 3.4601 no . 1_545
H8A O2 3.0547 no . 1_545
H8A C2 3.3470 no . 1_545
H8A C14 3.1959 no . 1_545
H8A C28 3.4059 no . 2_646
H8A H14A 2.3641 no . 1_545
H8A H14B 3.5006 no . 1_545
H8A H28A 3.1105 no . 2_646
H8A H28B 3.0053 no . 2_646
H8B F5 3.1845 no . 2_646
H8B O22 2.3571 no . 2_656
H8B C22 3.5209 no . 2_656
H8B H28B 3.0974 no . 2_646
H9A F6 2.9018 no . 2_746
H9A C14 3.2729 no . 1_545
H9A C26 3.1018 no . 2_746
H9A H14A 2.9332 no . 1_545
H9A H14B 2.8923 no . 1_545
H9A H26A 2.7570 no . 2_746
H9A H26B 2.6663 no . 2_746
H9B F6 2.7521 no . 2_746
H9B H23B 2.8598 no . 2_756
H11A C25 3.2693 no . 1_556
H11A C26 3.3354 no . 1_556
H11A H15C 3.0598 no . 2_647
H11A H24B 3.1012 no . 1_556
H11A H25B 2.6571 no . 1_556
H11A H26B 2.6363 no . 1_556
H11B F5 3.4806 no . 2_646
H11B O22 2.5275 no . 2_656
H11B C22 3.3839 no . 2_656
H11B H15B 3.5982 no . 2_647
H11B H15C 3.1904 no . 2_647
H11B H23A 3.0230 no . 2_656
H12A F4 2.8312 no . 2_757
H12A C24 3.4713 no . 2_756
H12A H23B 3.4063 no . 2_756
H12A H24A 3.3969 no . 2_756
H12A H24B 2.7868 no . 2_756
H12A H26B 3.3049 no . 1_556
H12B O22 3.5831 no . 2_656
H12B C24 3.5014 no . 2_756
H12B H23B 3.3376 no . 2_756
H12B H24A 3.0051 no . 2_756
H12B H24B 3.2131 no . 2_756
H13 O22 2.6212 no . 2_656
H13 C22 3.0988 no . 2_656
H13 C23 3.3579 no . 2_656
H13 C25 3.4106 no . 2_656
H13 H23A 2.8247 no . 2_656
H13 H25A 3.1931 no . 2_656
H13 H25B 2.8142 no . 2_656
H14A F3 2.8938 no . 1_565
H14A F5 3.4892 no . 2_656
H14A C8 3.1925 no . 1_565
H14A C9 3.3837 no . 1_565
H14A H8A 2.3641 no . 1_565
H14A H9A 2.9332 no . 1_565
H14A H25B 3.3444 no . 2_656
H14B F3 3.3092 no . 1_565
H14B F4 2.8077 no . 2_757
H14B C24 3.4023 no . 2_756
H14B C26 3.5462 no . 2_756
H14B H8A 3.5006 no . 1_565
H14B H9A 2.8923 no . 1_565
H14B H24A 3.1670 no . 2_756
H14B H24B 2.7792 no . 2_756
H14B H26A 3.1476 no . 2_756
H14B H26B 3.1128 no . 2_756
H15A F4 2.8985 no . 2_757
H15A F5 3.2033 no . 1_556
H15A F6 3.3915 no . 1_556
H15A C23 3.5094 no . 1_566
H15A H23A 3.1793 no . 1_566
H15A H23B 2.9063 no . 1_566
H15A H26B 3.1939 no . 1_556
H15B F3 3.2810 no . 2_657
H15B F5 2.6830 no . 1_556
H15B H11B 3.5982 no . 2_657
H15B H23A 3.1332 no . 2_656
H15B H25B 3.4688 no . 2_656
H15B H26B 3.2271 no . 1_556
H15C F3 3.3629 no . 1_565
H15C C11 3.5811 no . 2_657
H15C H11A 3.0598 no . 2_657
H15C H11B 3.1904 no . 2_657
H15C H23A 3.0808 no . 1_566
H15C H23B 3.5909 no . 1_566
H15C H25B 2.6926 no . 2_656
H23A F3 2.8845 no . 1_554
H23A C13 3.5984 no . 2_646
H23A C15 3.5646 no . 1_544
H23A H11B 3.0230 no . 2_646
H23A H13 2.8247 no . 2_646
H23A H15A 3.1793 no . 1_544
H23A H15B 3.1332 no . 2_646
H23A H15C 3.0808 no . 1_544
H23B F6 2.5935 no . 1_545
H23B H6B 3.4821 no . 2_746
H23B H9B 2.8598 no . 2_746
H23B H12A 3.4063 no . 2_746
H23B H12B 3.3376 no . 2_746
H23B H15A 2.9063 no . 1_544
H23B H15C 3.5909 no . 1_544
H24A O1 2.7145 no . 2_746
H24A C4 3.3548 no . 2_746
H24A C14 3.4444 no . 2_746
H24A H4B 2.3983 no . 2_746
H24A H12A 3.3969 no . 2_746
H24A H12B 3.0051 no . 2_746
H24A H14B 3.1670 no . 2_746
H24B F3 2.8288 no . 1_554
H24B F4 2.4986 no . 1_554
H24B O1 3.3764 no . 2_746
H24B C10 3.1710 no . 1_554
H24B C12 3.4145 no . 2_746
H24B C14 3.4306 no . 2_746
H24B H11A 3.1012 no . 1_554
H24B H12A 2.7868 no . 2_746
H24B H12B 3.2131 no . 2_746
H24B H14B 2.7792 no . 2_746
H25A O2 2.6602 no . 2_646
H25A H13 3.1931 no . 2_646
H25B F3 3.5319 no . 1_554
H25B O2 3.3688 no . 2_646
H25B C11 3.5736 no . 1_554
H25B C13 3.4428 no . 2_646
H25B C15 3.3257 no . 2_646
H25B H11A 2.6571 no . 1_554
H25B H13 2.8142 no . 2_646
H25B H14A 3.3444 no . 2_646
H25B H15B 3.4688 no . 2_646
H25B H15C 2.6926 no . 2_646
H26A F2 2.8115 no . 2_756
H26A O1 3.0286 no . 2_746
H26A C14 3.5772 no . 2_746
H26A H3A 3.5677 no . 2_746
H26A H9A 2.7570 no . 2_756
H26A H14B 3.1476 no . 2_746
H26B F4 3.4133 no . 1_554
H26B C9 3.5726 no . 2_756
H26B C11 3.4701 no . 1_554
H26B H9A 2.6663 no . 2_756
H26B H11A 2.6363 no . 1_554
H26B H12A 3.3049 no . 1_554
H26B H14B 3.1128 no . 2_746
H26B H15A 3.1939 no . 1_554
H26B H15B 3.2271 no . 1_554
H28A F1 3.1999 no . 2_656
H28A O2 2.3514 no . 2_646
H28A C2 3.4428 no . 2_646
H28A H8A 3.1105 no . 2_656
H28B F1 2.6952 no . 2_656
H28B O22 3.1744 no . 1_565
H28B C8 3.3864 no . 2_656
H28B C22 3.5433 no . 1_565
H28B C34 3.4620 no . 1_565
H28B H8A 3.0053 no . 2_656
H28B H8B 3.0974 no . 2_656
H28B H34A 2.5885 no . 1_565
H29A F2 2.7262 no . 2_756
H29A H3A 3.0519 no . 2_746
H29B F2 2.9924 no . 2_756
H29B C6 3.3132 no . 2_756
H29B H6A 2.8820 no . 2_756
H29B H6B 2.9627 no . 2_756
H29B H33 3.4512 no . 1_565
H29B H34A 3.1738 no . 1_565
H31A O2 2.6608 no . 2_646
H31A C2 3.4213 no . 2_646
H31A C3 3.5574 no . 2_646
H31A H3B 2.8309 no . 2_646
H31B F1 3.5768 no . .
H31B H3B 3.4297 no . 2_646
H31B H5A 3.0416 no . .
H31B H6A 2.9393 no . .
H32A C3 3.5952 no . 2_746
H32A C4 3.0879 no . 2_746
H32A H3A 3.0650 no . 2_746
H32A H4A 2.7914 no . 2_746
H32A H4B 2.6214 no . 2_746
H32B F8 2.9160 no . 2_746
H32B C4 3.4280 no . 2_746
H32B H3A 3.2900 no . 2_746
H32B H4A 2.7278 no . 2_746
H32B H4B 3.4053 no . 2_746
H32B H6A 3.1543 no . .
H33 F8 2.6186 no . 2_746
H33 C4 3.2288 no . 2_746
H33 H4A 2.5431 no . 2_746
H33 H4B 3.0420 no . 2_746
H33 H6A 3.1976 no . 2_746
H33 H6B 3.3728 no . 2_746
H33 H29B 3.4512 no . 1_545
H34A F1 3.4529 no . 2_646
H34A F7 3.3646 no . 1_545
H34A C28 3.4405 no . 1_545
H34A H5A 2.9554 no . 2_646
H34A H5B 3.4764 no . 2_646
H34A H28B 2.5885 no . 1_545
H34A H29B 3.1738 no . 1_545
H34B O2 2.9254 no . 2_646
H34B C2 3.3734 no . 2_646
H34B C3 3.5047 no . 2_646
H34B C5 3.2522 no . 2_646
H34B H3B 2.9476 no . 2_646
H34B H5A 2.6586 no . 2_646
H34B H5B 2.9914 no . 2_646
H35A F7 3.1054 no . 1_545
H35A C3 3.2934 no . 1_545
H35A H3A 2.8732 no . 1_545
H35A H3B 2.7847 no . 1_545
H35B F1 3.0735 no . .
H35B F7 3.0905 no . 2_646
H35B H3B 3.3362 no . 2_646
H35B H5A 3.3147 no . 2_646
H35C F1 2.8769 no . .
H35C F2 2.9539 no . .
H35C F8 3.0508 no . 2_746
H35C C3 3.5489 no . 1_545
H35C C6 3.5359 no . .
H35C C7 3.3393 no . .
H35C H3A 2.7818 no . 1_545
H35C H3B 3.4192 no . 1_545
H35C H6A 2.8351 no . .

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1427902'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;


_chemical_formula_sum            'C14 H24 F2 O2'
_chemical_formula_moiety         'C14 H24 F2 O2'
_chemical_formula_weight         262.34
_chemical_melting_point          ?
_chemical_absolute_configuration syn

#==============================================================================
# CRYSTAL DATA
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.3073(14)
_cell_length_b                   10.169(3)
_cell_length_c                   26.061(7)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     1406.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2855
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.35
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             568.00
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.997

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB P100'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            18749
_diffrn_reflns_av_R_equivalents  0.0769
_diffrn_reflns_theta_min         2.150
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_reflns_number_total             2577
_reflns_number_gt                2344
_reflns_threshold_expression     F²>2.0σ(F²)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0843
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2577
_refine_ls_number_parameters     164
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0403P)²+0.3260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.18
_refine_diff_density_min         -0.14
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 903 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(5)

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 for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_multiplicity
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.6502(3) 0.39466(13) -0.01349(5) 0.0299(4) Uani 1 4 0 d . . .
F2 F 0.2956(3) 0.47471(14) 0.01647(5) 0.0282(3) Uani 1 4 0 d . . .
O1 O 0.8238(3) 0.73090(15) 0.19419(6) 0.0229(4) Uani 1 4 0 d . . .
O2 O 0.6131(3) 0.65360(16) 0.26269(6) 0.0266(4) Uani 1 4 0 d . . .
C2 C 0.7963(5) 0.6505(2) 0.23533(8) 0.0195(5) Uani 1 4 0 d . . .
C3 C 1.0168(5) 0.5584(2) 0.24100(9) 0.0227(5) Uani 1 4 0 d . . .
C4 C 1.0445(5) 0.4644(2) 0.19508(9) 0.0212(5) Uani 1 4 0 d . . .
C5 C 0.8151(5) 0.3756(2) 0.18811(8) 0.0214(5) Uani 1 4 0 d . . .
C6 C 0.8452(5) 0.2729(2) 0.14540(9) 0.0251(5) Uani 1 4 0 d . . .
C7 C 0.8306(5) 0.3309(2) 0.09083(9) 0.0246(5) Uani 1 4 0 d . . .
C8 C 0.5614(5) 0.3638(2) 0.07443(9) 0.0216(5) Uani 1 4 0 d . . .
C9 C 0.5476(5) 0.4567(2) 0.02908(9) 0.0223(5) Uani 1 4 0 d . . .
C10 C 0.6712(5) 0.5903(2) 0.03419(8) 0.0220(5) Uani 1 4 0 d . . .
C11 C 0.5768(5) 0.6712(2) 0.07988(9) 0.0225(5) Uani 1 4 0 d . . .
C12 C 0.7423(5) 0.7926(2) 0.08848(9) 0.0216(5) Uani 1 4 0 d . . .
C13 C 0.6587(5) 0.8859(2) 0.13197(8) 0.0214(5) Uani 1 4 0 d . . .
C14 C 0.6075(5) 0.8142(2) 0.18216(9) 0.0215(5) Uani 1 4 0 d . . .
C15 C 0.4231(5) 0.9649(2) 0.11763(10) 0.0259(5) Uani 1 4 0 d . . .
H3A H 0.99534 0.50606 0.27273 0.0273 Uiso 1 4 0 calc R . .
H3B H 1.17319 0.61066 0.24458 0.0273 Uiso 1 4 0 calc R . .
H4A H 1.06978 0.51673 0.16345 0.0254 Uiso 1 4 0 calc R . .
H4B H 1.19592 0.4091 0.20014 0.0254 Uiso 1 4 0 calc R . .
H5A H 0.6667 0.43109 0.1803 0.0257 Uiso 1 4 0 calc R . .
H5B H 0.78141 0.32951 0.22085 0.0257 Uiso 1 4 0 calc R . .
H6A H 0.71175 0.2056 0.14925 0.0301 Uiso 1 4 0 calc R . .
H6B H 1.00977 0.22835 0.14964 0.0301 Uiso 1 4 0 calc R . .
H7A H 0.9341 0.41182 0.08937 0.0295 Uiso 1 4 0 calc R . .
H7B H 0.90306 0.26698 0.06626 0.0295 Uiso 1 4 0 calc R . .
H8A H 0.47303 0.28118 0.0655 0.0259 Uiso 1 4 0 calc R . .
H8B H 0.47179 0.40394 0.10383 0.0259 Uiso 1 4 0 calc R . .
H10A H 0.64098 0.6408 0.0023 0.0264 Uiso 1 4 0 calc R . .
H10B H 0.85545 0.57786 0.03765 0.0264 Uiso 1 4 0 calc R . .
H11A H 0.57821 0.61592 0.11115 0.0270 Uiso 1 4 0 calc R . .
H11B H 0.40096 0.69928 0.07349 0.0270 Uiso 1 4 0 calc R . .
H12A H 0.74808 0.84337 0.0561 0.0259 Uiso 1 4 0 calc R . .
H12B H 0.91592 0.76251 0.09591 0.0259 Uiso 1 4 0 calc R . .
H13 H 0.79868 0.94984 0.13817 0.0257 Uiso 1 4 0 calc R . .
H14A H 0.58023 0.87863 0.21009 0.0258 Uiso 1 4 0 calc R . .
H14B H 0.45387 0.75965 0.17886 0.0258 Uiso 1 4 0 calc R . .
H15A H 0.37663 1.02256 0.14623 0.0310 Uiso 1 4 0 calc R . .
H15B H 0.28388 0.90436 0.11036 0.0310 Uiso 1 4 0 calc R . .
H15C H 0.458 1.01821 0.08712 0.0310 Uiso 1 4 0 calc R . .



#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2013)'
_computing_molecular_graphics    'CrystalStructure 4.1'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
F1 C9 1.388(3) yes . .
F2 C9 1.389(3) yes . .
O1 C2 1.356(3) yes . .
O1 C14 1.461(3) yes . .
O2 C2 1.206(3) yes . .
C2 C3 1.507(3) yes . .
C3 C4 1.538(3) yes . .
C4 C5 1.527(3) yes . .
C5 C6 1.535(3) yes . .
C6 C7 1.542(3) yes . .
C7 C8 1.528(4) yes . .
C8 C9 1.515(3) yes . .
C9 C10 1.514(3) yes . .
C10 C11 1.532(3) yes . .
C11 C12 1.531(3) yes . .
C12 C13 1.544(3) yes . .
C13 C14 1.522(3) yes . .
C13 C15 1.533(4) yes . .
C3 H3A 0.990 no . .
C3 H3B 0.990 no . .
C4 H4A 0.990 no . .
C4 H4B 0.990 no . .
C5 H5A 0.990 no . .
C5 H5B 0.990 no . .
C6 H6A 0.990 no . .
C6 H6B 0.990 no . .
C7 H7A 0.990 no . .
C7 H7B 0.990 no . .
C8 H8A 0.990 no . .
C8 H8B 0.990 no . .
C10 H10A 0.990 no . .
C10 H10B 0.990 no . .
C11 H11A 0.990 no . .
C11 H11B 0.990 no . .
C12 H12A 0.990 no . .
C12 H12B 0.990 no . .
C13 H13 1.000 no . .
C14 H14A 0.990 no . .
C14 H14B 0.990 no . .
C15 H15A 0.980 no . .
C15 H15B 0.980 no . .
C15 H15C 0.980 no . .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
C2 O1 C14 115.76(18) yes . . .
O1 C2 O2 122.6(2) yes . . .
O1 C2 C3 111.63(19) yes . . .
O2 C2 C3 125.8(2) yes . . .
C2 C3 C4 112.59(19) yes . . .
C3 C4 C5 112.58(19) yes . . .
C4 C5 C6 113.9(2) yes . . .
C5 C6 C7 113.79(19) yes . . .
C6 C7 C8 112.9(2) yes . . .
C7 C8 C9 113.6(2) yes . . .
F1 C9 F2 104.38(18) yes . . .
F1 C9 C8 108.71(18) yes . . .
F1 C9 C10 107.97(19) yes . . .
F2 C9 C8 108.24(19) yes . . .
F2 C9 C10 108.66(19) yes . . .
C8 C9 C10 118.0(2) yes . . .
C9 C10 C11 114.1(2) yes . . .
C10 C11 C12 111.0(2) yes . . .
C11 C12 C13 116.0(2) yes . . .
C12 C13 C14 112.80(19) yes . . .
C12 C13 C15 112.19(19) yes . . .
C14 C13 C15 108.3(2) yes . . .
O1 C14 C13 108.78(19) yes . . .
C2 C3 H3A 109.079 no . . .
C2 C3 H3B 109.078 no . . .
C4 C3 H3A 109.073 no . . .
C4 C3 H3B 109.068 no . . .
H3A C3 H3B 107.840 no . . .
C3 C4 H4A 109.080 no . . .
C3 C4 H4B 109.084 no . . .
C5 C4 H4A 109.079 no . . .
C5 C4 H4B 109.085 no . . .
H4A C4 H4B 107.825 no . . .
C4 C5 H5A 108.765 no . . .
C4 C5 H5B 108.767 no . . .
C6 C5 H5A 108.760 no . . .
C6 C5 H5B 108.760 no . . .
H5A C5 H5B 107.660 no . . .
C5 C6 H6A 108.810 no . . .
C5 C6 H6B 108.802 no . . .
C7 C6 H6A 108.789 no . . .
C7 C6 H6B 108.804 no . . .
H6A C6 H6B 107.677 no . . .
C6 C7 H7A 109.007 no . . .
C6 C7 H7B 109.021 no . . .
C8 C7 H7A 109.016 no . . .
C8 C7 H7B 109.009 no . . .
H7A C7 H7B 107.791 no . . .
C7 C8 H8A 108.851 no . . .
C7 C8 H8B 108.850 no . . .
C9 C8 H8A 108.853 no . . .
C9 C8 H8B 108.851 no . . .
H8A C8 H8B 107.705 no . . .
C9 C10 H10A 108.731 no . . .
C9 C10 H10B 108.732 no . . .
C11 C10 H10A 108.728 no . . .
C11 C10 H10B 108.730 no . . .
H10A C10 H10B 107.635 no . . .
C10 C11 H11A 109.426 no . . .
C10 C11 H11B 109.432 no . . .
C12 C11 H11A 109.433 no . . .
C12 C11 H11B 109.434 no . . .
H11A C11 H11B 108.030 no . . .
C11 C12 H12A 108.283 no . . .
C11 C12 H12B 108.286 no . . .
C13 C12 H12A 108.282 no . . .
C13 C12 H12B 108.278 no . . .
H12A C12 H12B 107.394 no . . .
C12 C13 H13 107.764 no . . .
C14 C13 H13 107.773 no . . .
C15 C13 H13 107.768 no . . .
O1 C14 H14A 109.935 no . . .
O1 C14 H14B 109.926 no . . .
C13 C14 H14A 109.929 no . . .
C13 C14 H14B 109.942 no . . .
H14A C14 H14B 108.318 no . . .
C13 C15 H15A 109.471 no . . .
C13 C15 H15B 109.477 no . . .
C13 C15 H15C 109.468 no . . .
H15A C15 H15B 109.473 no . . .
H15A C15 H15C 109.474 no . . .
H15B C15 H15C 109.464 no . . .

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_publ_flag
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C2 O1 C14 C13 -173.73(15) no . . . .
C14 O1 C2 O2 -5.2(3) no . . . .
C14 O1 C2 C3 173.67(15) no . . . .
O1 C2 C3 C4 -62.8(2) no . . . .
O2 C2 C3 C4 116.0(2) no . . . .
C2 C3 C4 C5 -61.2(2) no . . . .
C3 C4 C5 C6 -175.25(16) no . . . .
C4 C5 C6 C7 -73.3(2) no . . . .
C5 C6 C7 C8 -76.3(3) no . . . .
C6 C7 C8 C9 162.48(17) no . . . .
C7 C8 C9 F1 64.7(2) no . . . .
C7 C8 C9 F2 177.52(17) no . . . .
C7 C8 C9 C10 -58.6(3) no . . . .
F1 C9 C10 C11 -179.95(16) no . . . .
F2 C9 C10 C11 67.4(2) no . . . .
C8 C9 C10 C11 -56.3(3) no . . . .
C9 C10 C11 C12 169.50(17) no . . . .
C10 C11 C12 C13 177.17(17) no . . . .
C11 C12 C13 C14 50.0(3) no . . . .
C11 C12 C13 C15 -72.7(2) no . . . .
C12 C13 C14 O1 51.0(2) no . . . .
C15 C13 C14 O1 175.78(16) no . . . .

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_publ_flag
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
F1 C7 2.954(3) no . .
F2 C11 2.992(3) no . .
O1 C4 2.952(3) no . .
O1 C11 3.311(3) no . .
O1 C12 2.858(3) no . .
O2 C4 3.471(3) no . .
O2 C5 3.594(3) no . .
O2 C14 2.660(3) no . .
C2 C5 3.056(3) no . .
C4 C7 3.242(3) no . .
C5 C8 3.256(3) no . .
C7 C10 3.139(3) no . .
C8 C11 3.130(3) no . .
C11 C14 3.041(3) no . .
C11 C15 3.249(3) no . .
F1 C7 3.493(3) no . 2_455
F1 C15 3.392(3) no . 2_565
F2 C7 3.462(3) no . 1_455
F2 C10 3.546(3) no . 1_455
O2 C3 3.357(3) no . 1_455
O2 C5 3.451(3) no . 3_655
C3 O2 3.357(3) no . 1_655
C5 O2 3.451(3) no . 3_645
C7 F1 3.493(3) no . 2_555
C7 F2 3.462(3) no . 1_655
C10 F2 3.546(3) no . 1_655
C15 F1 3.392(3) no . 2_465
F1 H7A 3.0800 no . .
F1 H7B 2.7940 no . .
F1 H8A 2.5404 no . .
F1 H8B 3.2022 no . .
F1 H10A 2.5371 no . .
F1 H10B 2.5364 no . .
F2 H8A 2.5284 no . .
F2 H8B 2.5643 no . .
F2 H10A 2.5197 no . .
F2 H10B 3.1989 no . .
F2 H11A 3.2249 no . .
F2 H11B 2.7814 no . .
O1 H3A 3.2010 no . .
O1 H3B 2.5804 no . .
O1 H4A 2.6627 no . .
O1 H5A 3.1814 no . .
O1 H11A 2.7837 no . .
O1 H12B 2.6273 no . .
O1 H13 2.6658 no . .
O2 H3A 2.5367 no . .
O2 H3B 3.0413 no . .
O2 H5A 3.1323 no . .
O2 H5B 3.5845 no . .
O2 H14A 2.6733 no . .
O2 H14B 2.5788 no . .
C2 H4A 2.7327 no . .
C2 H4B 3.3716 no . .
C2 H5A 2.7402 no . .
C2 H5B 3.2871 no . .
C2 H11A 3.4549 no . .
C2 H14A 2.6699 no . .
C2 H14B 2.5883 no . .
C3 H5A 2.7624 no . .
C3 H5B 2.6934 no . .
C4 H6A 3.3872 no . .
C4 H6B 2.6833 no . .
C4 H7A 2.8669 no . .
C5 H3A 2.7456 no . .
C5 H3B 3.3898 no . .
C5 H7A 2.6751 no . .
C5 H7B 3.3945 no . .
C5 H8B 2.8683 no . .
C5 H11A 3.4023 no . .
C6 H4A 2.7911 no . .
C6 H4B 2.7236 no . .
C6 H8A 2.8714 no . .
C6 H8B 2.6225 no . .
C7 H4A 2.9604 no . .
C7 H4B 3.5364 no . .
C7 H5A 2.6892 no . .
C7 H5B 3.3986 no . .
C7 H10B 2.8715 no . .
C7 H11A 3.2367 no . .
C8 H5A 2.8971 no . .
C8 H6A 2.6507 no . .
C8 H6B 3.3765 no . .
C8 H10A 3.4128 no . .
C8 H10B 2.8448 no . .
C8 H11A 2.7382 no . .
C8 H11B 3.5165 no . .
C9 H7A 2.6239 no . .
C9 H7B 2.8673 no . .
C9 H11A 2.6872 no . .
C9 H11B 2.8334 no . .
C10 H7A 2.7035 no . .
C10 H8A 3.4139 no . .
C10 H8B 2.8295 no . .
C10 H12A 2.6674 no . .
C10 H12B 2.7093 no . .
C11 H7A 3.2580 no . .
C11 H8B 2.8436 no . .
C11 H13 3.4241 no . .
C11 H14B 2.8087 no . .
C11 H15B 2.9445 no . .
C11 H15C 3.5898 no . .
C12 H10A 2.7776 no . .
C12 H10B 2.6235 no . .
C12 H14A 3.3986 no . .
C12 H14B 2.8290 no . .
C12 H15A 3.3915 no . .
C12 H15B 2.7453 no . .
C12 H15C 2.7465 no . .
C13 H11A 2.8315 no . .
C13 H11B 2.7925 no . .
C14 H11A 2.7414 no . .
C14 H11B 3.2540 no . .
C14 H12A 3.3819 no . .
C14 H12B 2.8299 no . .
C14 H15A 2.6206 no . .
C14 H15B 2.7004 no . .
C14 H15C 3.3269 no . .
C15 H11B 2.9381 no . .
C15 H12A 2.6596 no . .
C15 H12B 3.3760 no . .
C15 H14A 2.6965 no . .
C15 H14B 2.6323 no . .
H3A H4A 2.8773 no . .
H3A H4B 2.3842 no . .
H3A H5A 3.0702 no . .
H3A H5B 2.5181 no . .
H3B H4A 2.3841 no . .
H3B H4B 2.3574 no . .
H3B H5B 3.5889 no . .
H4A H5A 2.3511 no . .
H4A H5B 2.8644 no . .
H4A H6B 2.9717 no . .
H4A H7A 2.3203 no . .
H4A H10B 3.5255 no . .
H4A H11A 3.1115 no . .
H4A H12B 3.1642 no . .
H4B H5A 2.8647 no . .
H4B H5B 2.4054 no . .
H4B H6A 3.5559 no . .
H4B H6B 2.4671 no . .
H4B H7A 3.2039 no . .
H5A H6A 2.4434 no . .
H5A H6B 2.8643 no . .
H5A H7A 2.7691 no . .
H5A H8A 3.5116 no . .
H5A H8B 2.2623 no . .
H5A H11A 2.6460 no . .
H5A H14B 3.5272 no . .
H5B H6A 2.2817 no . .
H5B H6B 2.4436 no . .
H5B H8B 3.5459 no . .
H6A H7A 2.8681 no . .
H6A H7B 2.4695 no . .
H6A H8A 2.6381 no . .
H6A H8B 2.6629 no . .
H6B H7A 2.4717 no . .
H6B H7B 2.2797 no . .
H6B H8B 3.5730 no . .
H7A H8A 2.8531 no . .
H7A H8B 2.4837 no . .
H7A H10B 2.2005 no . .
H7A H11A 2.8632 no . .
H7A H12B 3.5716 no . .
H7B H8A 2.2869 no . .
H7B H8B 2.8526 no . .
H7B H10B 3.2580 no . .
H8B H10B 3.2014 no . .
H8B H11A 2.2366 no . .
H8B H11B 3.1284 no . .
H10A H11A 2.8674 no . .
H10A H11B 2.3278 no . .
H10A H12A 2.5559 no . .
H10A H12B 3.1004 no . .
H10B H11A 2.4462 no . .
H10B H11B 2.8662 no . .
H10B H12A 2.8011 no . .
H10B H12B 2.4360 no . .
H11A H12A 2.8672 no . .
H11A H12B 2.3648 no . .
H11A H14B 2.3845 no . .
H11A H15B 3.3233 no . .
H11B H12A 2.3972 no . .
H11B H12B 2.8678 no . .
H11B H14B 2.8278 no . .
H11B H15B 2.3788 no . .
H11B H15C 3.2767 no . .
H12A H13 2.4123 no . .
H12A H15A 3.5671 no . .
H12A H15B 2.9076 no . .
H12A H15C 2.4870 no . .
H12B H13 2.2867 no . .
H12B H14B 3.2692 no . .
H12B H15C 3.5666 no . .
H13 H14A 2.3198 no . .
H13 H14B 2.8660 no . .
H13 H15A 2.3682 no . .
H13 H15B 2.8643 no . .
H13 H15C 2.3500 no . .
H14A H15A 2.4657 no . .
H14A H15B 3.0492 no . .
H14A H15C 3.5645 no . .
H14B H15A 2.8354 no . .
H14B H15B 2.4832 no . .
H14B H15C 3.5539 no . .
F1 H7B 2.5128 no . 2_455
F1 H8A 2.8231 no . 2_555
F1 H12A 3.5896 no . 2_465
F1 H15B 3.3247 no . 2_565
F1 H15C 2.6712 no . 2_565
F2 H7A 2.7748 no . 1_455
F2 H7B 3.2383 no . 1_455
F2 H7B 3.3188 no . 2_455
F2 H10B 2.6196 no . 1_455
F2 H12A 2.6576 no . 2_465
F2 H15C 3.2410 no . 2_465
O1 H3A 3.0813 no . 3_755
O1 H4B 3.2983 no . 3_755
O1 H5B 3.2092 no . 3_755
O1 H14B 3.3805 no . 1_655
O2 H3B 2.4217 no . 1_455
O2 H4B 2.9524 no . 3_755
O2 H5A 3.5179 no . 3_655
O2 H5B 2.7872 no . 3_655
O2 H6A 2.9187 no . 3_655
O2 H6B 3.1311 no . 3_755
O2 H14A 3.0619 no . 3_645
O2 H15A 2.7227 no . 3_645
C2 H3B 3.3402 no . 1_455
C2 H4B 3.1216 no . 3_755
C2 H5B 3.1051 no . 3_755
C2 H6B 3.2670 no . 3_755
C2 H15A 3.4732 no . 3_645
C3 H5B 3.1203 no . 3_755
C3 H6A 3.5351 no . 3_755
C3 H6B 3.3361 no . 3_755
C3 H13 3.4776 no . 3_745
C3 H14A 3.0888 no . 3_745
C3 H14B 3.4917 no . 1_655
C4 H5A 3.3419 no . 1_655
C4 H8B 3.3432 no . 1_655
C4 H14A 3.2918 no . 3_745
C5 H3B 3.2157 no . 3_745
C5 H4B 3.3187 no . 1_455
C5 H14A 3.3826 no . 3_645
C6 H3A 3.5541 no . 3_745
C6 H3B 3.3094 no . 3_745
C6 H13 3.2998 no . 1_545
C6 H15A 3.5589 no . 1_545
C7 H8A 3.5093 no . 1_655
C7 H8B 3.4993 no . 1_655
C8 H7A 3.3876 no . 1_455
C8 H15C 3.5723 no . 1_545
C9 H7B 3.4552 no . 2_455
C9 H12A 3.4040 no . 2_465
C10 H12A 3.3219 no . 2_465
C12 H10A 3.2456 no . 2_565
C12 H15B 3.1432 no . 1_655
C13 H3A 3.3213 no . 3_755
C13 H6A 3.2938 no . 1_565
C13 H15B 3.3704 no . 1_655
C14 H3A 3.1034 no . 3_755
C14 H3B 3.4992 no . 1_455
C14 H4B 3.3806 no . 3_755
C14 H5B 3.2671 no . 3_655
C15 H6A 3.0032 no . 1_565
C15 H6B 3.5618 no . 1_465
C15 H8A 3.5017 no . 1_565
C15 H12B 3.4352 no . 1_455
C15 H13 3.3603 no . 1_455
H3A O1 3.0813 no . 3_745
H3A C6 3.5541 no . 3_755
H3A C13 3.3213 no . 3_745
H3A C14 3.1034 no . 3_745
H3A H5B 3.5002 no . 3_755
H3A H6A 3.2663 no . 3_755
H3A H6B 3.0338 no . 3_755
H3A H13 2.6294 no . 3_745
H3A H14A 3.3483 no . 3_645
H3A H14A 2.6370 no . 3_745
H3A H15A 2.8959 no . 3_645
H3A H15B 3.5424 no . 3_645
H3B O2 2.4217 no . 1_655
H3B C2 3.3402 no . 1_655
H3B C5 3.2157 no . 3_755
H3B C6 3.3094 no . 3_755
H3B C14 3.4992 no . 1_655
H3B H5B 2.4131 no . 3_755
H3B H6A 2.9935 no . 3_755
H3B H6B 3.1583 no . 3_755
H3B H13 3.4690 no . 3_745
H3B H14A 3.5918 no . 1_655
H3B H14A 2.9455 no . 3_745
H3B H14B 2.7291 no . 1_655
H4A H5A 3.3148 no . 1_655
H4A H8B 2.8778 no . 1_655
H4A H11A 3.1869 no . 1_655
H4A H11B 3.4687 no . 1_655
H4A H14B 3.2279 no . 1_655
H4B O1 3.2983 no . 3_745
H4B O2 2.9524 no . 3_745
H4B C2 3.1216 no . 3_745
H4B C5 3.3187 no . 1_655
H4B C14 3.3806 no . 3_745
H4B H5A 2.5613 no . 1_655
H4B H5B 3.2561 no . 1_655
H4B H8B 2.9062 no . 1_655
H4B H14A 2.6421 no . 3_745
H5A O2 3.5179 no . 3_645
H5A C4 3.3419 no . 1_455
H5A H4A 3.3148 no . 1_455
H5A H4B 2.5613 no . 1_455
H5A H14A 3.1878 no . 3_645
H5B O1 3.2092 no . 3_745
H5B O2 2.7872 no . 3_645
H5B C2 3.1051 no . 3_745
H5B C3 3.1203 no . 3_745
H5B C14 3.2671 no . 3_645
H5B H3A 3.5002 no . 3_745
H5B H3B 2.4131 no . 3_745
H5B H4B 3.2561 no . 1_455
H5B H14A 2.6782 no . 3_645
H5B H14B 2.9825 no . 3_645
H6A O2 2.9187 no . 3_645
H6A C3 3.5351 no . 3_745
H6A C13 3.2938 no . 1_545
H6A C15 3.0032 no . 1_545
H6A H3A 3.2663 no . 3_745
H6A H3B 2.9935 no . 3_745
H6A H13 2.6572 no . 1_545
H6A H15A 2.5757 no . 1_545
H6A H15C 2.8402 no . 1_545
H6B O2 3.1311 no . 3_745
H6B C2 3.2670 no . 3_745
H6B C3 3.3361 no . 3_745
H6B C15 3.5618 no . 1_645
H6B H3A 3.0338 no . 3_745
H6B H3B 3.1583 no . 3_745
H6B H8A 3.3380 no . 1_655
H6B H8B 3.2598 no . 1_655
H6B H13 3.0604 no . 1_545
H6B H15A 2.8598 no . 1_645
H6B H15C 3.5890 no . 1_645
H7A F2 2.7748 no . 1_655
H7A C8 3.3876 no . 1_655
H7A H8A 3.2145 no . 1_655
H7A H8B 2.8796 no . 1_655
H7B F1 2.5128 no . 2_555
H7B F2 3.2383 no . 1_655
H7B F2 3.3188 no . 2_555
H7B C9 3.4552 no . 2_555
H7B H8A 3.0285 no . 1_655
H7B H8A 3.4884 no . 2_555
H7B H8B 3.4655 no . 1_655
H7B H15C 3.5036 no . 1_545
H8A F1 2.8231 no . 2_455
H8A C7 3.5093 no . 1_455
H8A C15 3.5017 no . 1_545
H8A H6B 3.3380 no . 1_455
H8A H7A 3.2145 no . 1_455
H8A H7B 3.0285 no . 1_455
H8A H7B 3.4884 no . 2_455
H8A H15A 3.4066 no . 1_545
H8A H15C 2.7341 no . 1_545
H8B C4 3.3432 no . 1_455
H8B C7 3.4993 no . 1_455
H8B H4A 2.8778 no . 1_455
H8B H4B 2.9062 no . 1_455
H8B H6B 3.2598 no . 1_455
H8B H7A 2.8796 no . 1_455
H8B H7B 3.4655 no . 1_455
H10A C12 3.2456 no . 2_465
H10A H10A 3.4625 no . 2_465
H10A H10A 3.4625 no . 2_565
H10A H10B 3.4009 no . 2_465
H10A H11B 2.9069 no . 2_565
H10A H12A 2.5866 no . 2_465
H10A H12A 3.5671 no . 2_565
H10A H12B 2.9907 no . 2_465
H10A H15B 3.0670 no . 2_565
H10A H15C 3.2979 no . 2_565
H10B F2 2.6196 no . 1_655
H10B H10A 3.4009 no . 2_565
H10B H11B 3.2832 no . 1_655
H10B H12A 3.3096 no . 2_565
H10B H15C 3.4386 no . 2_565
H11A H4A 3.1869 no . 1_455
H11B H4A 3.4687 no . 1_455
H11B H10A 2.9069 no . 2_465
H11B H10B 3.2832 no . 1_455
H11B H12A 3.5003 no . 2_465
H11B H12B 2.7169 no . 1_455
H12A F1 3.5896 no . 2_565
H12A F2 2.6576 no . 2_565
H12A C9 3.4040 no . 2_565
H12A C10 3.3219 no . 2_565
H12A H10A 3.5671 no . 2_465
H12A H10A 2.5866 no . 2_565
H12A H10B 3.3096 no . 2_465
H12A H11B 3.5003 no . 2_565
H12A H15B 3.2358 no . 1_655
H12B C15 3.4352 no . 1_655
H12B H10A 2.9907 no . 2_565
H12B H11B 2.7169 no . 1_655
H12B H14B 3.5813 no . 1_655
H12B H15B 2.4569 no . 1_655
H13 C3 3.4776 no . 3_755
H13 C6 3.2998 no . 1_565
H13 C15 3.3603 no . 1_655
H13 H3A 2.6294 no . 3_755
H13 H3B 3.4690 no . 3_755
H13 H6A 2.6572 no . 1_565
H13 H6B 3.0604 no . 1_565
H13 H15A 3.1622 no . 1_655
H13 H15B 2.7148 no . 1_655
H14A O2 3.0619 no . 3_655
H14A C3 3.0888 no . 3_755
H14A C4 3.2918 no . 3_755
H14A C5 3.3826 no . 3_655
H14A H3A 3.3483 no . 3_655
H14A H3A 2.6370 no . 3_755
H14A H3B 3.5918 no . 1_455
H14A H3B 2.9455 no . 3_755
H14A H4B 2.6421 no . 3_755
H14A H5A 3.1878 no . 3_655
H14A H5B 2.6782 no . 3_655
H14B O1 3.3805 no . 1_455
H14B C3 3.4917 no . 1_455
H14B H3B 2.7291 no . 1_455
H14B H4A 3.2279 no . 1_455
H14B H5B 2.9825 no . 3_655
H14B H12B 3.5813 no . 1_455
H15A O2 2.7227 no . 3_655
H15A C2 3.4732 no . 3_655
H15A C6 3.5589 no . 1_565
H15A H3A 2.8959 no . 3_655
H15A H6A 2.5757 no . 1_565
H15A H6B 2.8598 no . 1_465
H15A H8A 3.4066 no . 1_565
H15A H13 3.1622 no . 1_455
H15B F1 3.3247 no . 2_465
H15B C12 3.1432 no . 1_455
H15B C13 3.3704 no . 1_455
H15B H3A 3.5424 no . 3_655
H15B H10A 3.0670 no . 2_465
H15B H12A 3.2358 no . 1_455
H15B H12B 2.4569 no . 1_455
H15B H13 2.7148 no . 1_455
H15C F1 2.6712 no . 2_465
H15C F2 3.2410 no . 2_565
H15C C8 3.5723 no . 1_565
H15C H6A 2.8402 no . 1_565
H15C H6B 3.5890 no . 1_465
H15C H7B 3.5036 no . 1_565
H15C H8A 2.7341 no . 1_565
H15C H10A 3.2979 no . 2_465
H15C H10B 3.4386 no . 2_465

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1427903'
_audit_update_record             
;
2015-09-28 deposited with the CCDC.
2015-11-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H25 N O3'
_chemical_formula_weight         267.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.7556(12)
_cell_length_b                   10.6790(15)
_cell_length_c                   9.8996(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.033(4)
_cell_angle_gamma                90
_cell_volume                     783.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_F_000             292
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.625
_shelx_estimated_absorpt_T_min   0.849
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8393
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.672
_diffrn_reflns_theta_max         68.041
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.961
_reflns_number_total             2736
_reflns_number_gt                2625
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.823
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    0.924

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.10(14)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2736
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1176
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   0.891
_refine_ls_restrained_S_all      0.890
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8963(2) 0.00836(16) 0.86687(17) 0.0368(4) Uani 1 1 d . . . . .
O2 O 0.9002(3) 0.19676(18) 0.96535(17) 0.0422(5) Uani 1 1 d . . . . .
O3 O 0.9922(3) 0.29732(19) 0.57981(17) 0.0457(5) Uani 1 1 d . . . . .
N3 N 0.9049(3) 0.17340(17) 0.7312(2) 0.0298(4) Uani 1 1 d . . . . .
C2 C 0.9021(3) 0.1339(2) 0.8657(2) 0.0321(5) Uani 1 1 d . . . . .
C4 C 0.8630(3) 0.0667(2) 0.6328(2) 0.0308(5) Uani 1 1 d . . . . .
H4 H 0.9395 0.0719 0.5674 0.037 Uiso 1 1 calc R U . . .
C5 C 0.9308(3) -0.0416(2) 0.7376(2) 0.0336(5) Uani 1 1 d . . . . .
C6 C 0.9705(3) 0.2866(2) 0.6961(2) 0.0319(5) Uani 1 1 d . . . . .
C7 C 1.0044(3) 0.3929(2) 0.8020(2) 0.0311(5) Uani 1 1 d . . . . .
H7 H 1.0437 0.3572 0.8997 0.037 Uiso 1 1 calc R U . . .
C8 C 1.1521(3) 0.4791(2) 0.7825(3) 0.0375(5) Uani 1 1 d . . . . .
H8A H 1.1168 0.5099 0.6839 0.045 Uiso 1 1 calc R U . . .
H8B H 1.1627 0.5525 0.8455 0.045 Uiso 1 1 calc R U . . .
C9 C 1.3363(4) 0.4145(3) 0.8146(3) 0.0461(6) Uani 1 1 d . . . . .
H9A H 1.3277 0.3448 0.7470 0.055 Uiso 1 1 calc R U . . .
H9B H 1.4255 0.4753 0.7999 0.055 Uiso 1 1 calc R U . . .
C10 C 1.4016(4) 0.3645(3) 0.9608(3) 0.0510(7) Uani 1 1 d . . . . .
H10 H 1.4067 0.4212 1.0359 0.061 Uiso 1 1 calc R U . . .
C11 C 1.4529(5) 0.2490(4) 0.9950(4) 0.0682(9) Uani 1 1 d . . . . .
H11A H 1.4500 0.1892 0.9233 0.082 Uiso 1 1 calc R U . . .
H11B H 1.4930 0.2249 1.0916 0.082 Uiso 1 1 calc R U . . .
C12 C 0.8256(4) 0.4626(3) 0.7808(3) 0.0469(6) Uani 1 1 d . . . . .
H12A H 0.7850 0.4967 0.6848 0.056 Uiso 1 1 calc R U . . .
H12B H 0.8428 0.5312 0.8493 0.056 Uiso 1 1 calc R U . . .
H12C H 0.7346 0.4045 0.7949 0.056 Uiso 1 1 calc R U . . .
C13 C 0.6624(3) 0.0659(3) 0.5451(3) 0.0392(5) Uani 1 1 d . . . . .
H13 H 0.6390 -0.0154 0.4928 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6222(4) 0.1701(3) 0.4353(3) 0.0462(6) Uani 1 1 d . . . . .
H14A H 0.6347 0.2514 0.4830 0.055 Uiso 1 1 calc R U . . .
H14B H 0.4988 0.1608 0.3730 0.055 Uiso 1 1 calc R U . . .
H14C H 0.7072 0.1651 0.3792 0.055 Uiso 1 1 calc R U . . .
C15 C 0.5308(4) 0.0742(4) 0.6333(3) 0.0566(8) Uani 1 1 d . . . . .
H15A H 0.4070 0.0667 0.5713 0.068 Uiso 1 1 calc R U . . .
H15B H 0.5456 0.1551 0.6823 0.068 Uiso 1 1 calc R U . . .
H15C H 0.5555 0.0063 0.7030 0.068 Uiso 1 1 calc R U . . .
C16 C 1.1322(4) -0.0595(3) 0.7700(3) 0.0445(6) Uani 1 1 d . . . . .
H16A H 1.1755 -0.1145 0.8523 0.053 Uiso 1 1 calc R U . . .
H16B H 1.1927 0.0219 0.7904 0.053 Uiso 1 1 calc R U . . .
H16C H 1.1591 -0.0976 0.6884 0.053 Uiso 1 1 calc R U . . .
C17 C 0.8340(4) -0.1657(3) 0.7043(3) 0.0473(7) Uani 1 1 d . . . . .
H17A H 0.7053 -0.1536 0.6932 0.057 Uiso 1 1 calc R U . . .
H17B H 0.8845 -0.2246 0.7817 0.057 Uiso 1 1 calc R U . . .
H17C H 0.8494 -0.1993 0.6165 0.057 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.341(3) . ?
O1 C5 1.481(3) . ?
O2 C2 1.197(3) . ?
O3 C6 1.217(3) . ?
N3 C2 1.403(3) . ?
N3 C6 1.395(3) . ?
N3 C4 1.473(3) . ?
C4 C13 1.543(3) . ?
C4 C5 1.540(3) . ?
C4 H4 1.0000 . ?
C5 C17 1.511(3) . ?
C5 C16 1.512(4) . ?
C6 C7 1.515(3) . ?
C7 C12 1.533(3) . ?
C7 C8 1.524(3) . ?
C7 H7 1.0000 . ?
C8 C9 1.533(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.486(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.310(6) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9500 . ?
C11 H11B 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.523(4) . ?
C13 C15 1.528(4) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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 O1 C5 109.74(18) . . ?
C2 N3 C6 127.28(19) . . ?
C2 N3 C4 109.48(18) . . ?
C6 N3 C4 122.13(18) . . ?
O2 C2 O1 123.0(2) . . ?
O2 C2 N3 128.3(2) . . ?
O1 C2 N3 108.6(2) . . ?
N3 C4 C13 111.6(2) . . ?
N3 C4 C5 99.74(15) . . ?
C13 C4 C5 117.6(2) . . ?
N3 C4 H4 109.1 . . ?
C13 C4 H4 109.1 . . ?
C5 C4 H4 109.1 . . ?
O1 C5 C17 107.5(2) . . ?
O1 C5 C16 107.4(2) . . ?
C17 C5 C16 110.6(2) . . ?
O1 C5 C4 101.50(18) . . ?
C17 C5 C4 117.5(2) . . ?
C16 C5 C4 111.5(2) . . ?
O3 C6 N3 118.6(2) . . ?
O3 C6 C7 122.7(2) . . ?
N3 C6 C7 118.63(19) . . ?
C6 C7 C12 107.6(2) . . ?
C6 C7 C8 110.43(19) . . ?
C12 C7 C8 111.9(2) . . ?
C6 C7 H7 109.0 . . ?
C12 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
C9 C8 C7 113.1(2) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 113.2(2) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 125.5(3) . . ?
C11 C10 H10 117.2 . . ?
C9 C10 H10 117.2 . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C15 109.5(2) . . ?
C14 C13 C4 111.0(2) . . ?
C15 C13 C4 114.2(2) . . ?
C14 C13 H13 107.3 . . ?
C15 C13 H13 107.3 . . ?
C4 C13 H13 107.3 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C5 C16 H16A 109.5 . . ?
C5 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C5 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C5 O1 C2 O2 -170.8(2) . . . . ?
C5 O1 C2 N3 11.0(3) . . . . ?
C6 N3 C2 O2 25.5(4) . . . . ?
C4 N3 C2 O2 -166.5(2) . . . . ?
C6 N3 C2 O1 -156.4(2) . . . . ?
C4 N3 C2 O1 11.6(3) . . . . ?
C2 N3 C4 C13 97.6(2) . . . . ?
C6 N3 C4 C13 -93.7(2) . . . . ?
C2 N3 C4 C5 -27.4(2) . . . . ?
C6 N3 C4 C5 141.3(2) . . . . ?
C2 O1 C5 C17 -151.5(2) . . . . ?
C2 O1 C5 C16 89.5(3) . . . . ?
C2 O1 C5 C4 -27.6(2) . . . . ?
N3 C4 C5 O1 31.5(2) . . . . ?
C13 C4 C5 O1 -89.2(2) . . . . ?
N3 C4 C5 C17 148.4(2) . . . . ?
C13 C4 C5 C17 27.6(3) . . . . ?
N3 C4 C5 C16 -82.6(2) . . . . ?
C13 C4 C5 C16 156.7(2) . . . . ?
C2 N3 C6 O3 167.2(2) . . . . ?
C4 N3 C6 O3 0.5(3) . . . . ?
C2 N3 C6 C7 -15.3(3) . . . . ?
C4 N3 C6 C7 178.07(19) . . . . ?
O3 C6 C7 C12 92.3(3) . . . . ?
N3 C6 C7 C12 -85.1(3) . . . . ?
O3 C6 C7 C8 -30.1(3) . . . . ?
N3 C6 C7 C8 152.5(2) . . . . ?
C6 C7 C8 C9 -64.7(3) . . . . ?
C12 C7 C8 C9 175.4(2) . . . . ?
C7 C8 C9 C10 -58.7(3) . . . . ?
C8 C9 C10 C11 126.2(3) . . . . ?
N3 C4 C13 C14 72.2(3) . . . . ?
C5 C4 C13 C14 -173.5(2) . . . . ?
N3 C4 C13 C15 -52.2(3) . . . . ?
C5 C4 C13 C15 62.1(3) . . . . ?

_refine_diff_density_max         0.326
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.160

_shelxl_version_number           2014-3

