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

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

data_JSRDCC
_database_code_depnum_ccdc_archive 'CCDC 1470483'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;

_nottingham_internal_coll_name   JSRDCC
_nottingham_internal_coll_number 10309
_nottingham_internal_coll_client JS/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '30 and 120'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   wl
_nottingham_internal_coll_date   30/3/2011
_nottingham_internal_process_user wl
_nottingham_internal_process_date 31/03/2011
_nottingham_internal_solution_user wl
_nottingham_internal_solution_date 31/3/2011
_nottingham_internal_refinement_user wl
_nottingham_internal_refinement_date 31/3/2011
_nottingham_internal_validation_user wl
_nottingham_internal_validation_date 1/4/2011
_nottingham_internal_archive_date 1/4/2011

_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. 
;

_audit_creation_method           'enCIFer editing of SHELXL-97 created file'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H29 Cl3 O3'
_chemical_formula_sum            'C17 H29 Cl3 O3'
_chemical_formula_weight         387.75
_chemical_absolute_configuration ad

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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   5.1865(3)
_cell_length_b                   9.3623(5)
_cell_length_c                   40.6608(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1974.38(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    4779
_cell_measurement_theta_min      3.26
_cell_measurement_theta_max      74.37

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4221
_exptl_crystal_size_mid          0.0789
_exptl_crystal_size_min          0.0506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    4.291
_exptl_absorpt_correction_T_min  0.3
_exptl_absorpt_correction_T_max  1.096
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
;

_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3613
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10046
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         4.35
_diffrn_reflns_theta_max         74.54
_reflns_number_total             3919
_reflns_number_gt                3563
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.36 (release 02-08-2010 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    ' ? '
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0055P)²+8.0722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_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 H D (1983), Acta Cryst. A39, 876-881, 1503 Friedel pairs measured'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         3919
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1382
_refine_ls_goodness_of_fit_ref   1.218
_refine_ls_restrained_S_all      1.218
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.1499(11) 0.5909(6) 0.48164(12) 0.0206(12) Uani 1 1 d . . .
O1 O -0.0187(8) 0.6862(4) 0.47093(9) 0.0243(8) Uani 1 1 d . . .
O2 O -0.3670(7) 0.5433(4) 0.46725(9) 0.0222(8) Uani 1 1 d . . .
C2 C -0.1020(11) 0.5086(6) 0.51211(13) 0.0213(11) Uani 1 1 d . . .
H2 H -0.2383 0.4544 0.5215 0.026 Uiso 1 1 calc R . .
C3 C 0.1258(12) 0.5088(6) 0.52657(12) 0.0223(12) Uani 1 1 d . . .
H3 H 0.2659 0.5578 0.5166 0.027 Uiso 1 1 calc R . .
C4 C 0.1652(11) 0.4323(6) 0.55854(13) 0.0212(11) Uani 1 1 d . . .
H4 H -0.0026 0.3895 0.5656 0.025 Uiso 1 1 calc R . .
Cl1 Cl 0.3984(3) 0.28870(15) 0.55249(3) 0.0247(3) Uani 1 1 d . . .
C5 C 0.2586(10) 0.5342(6) 0.58550(13) 0.0199(11) Uani 1 1 d . . .
H5 H 0.1273 0.6115 0.5884 0.024 Uiso 1 1 calc R . .
O3 O 0.4996(8) 0.5985(4) 0.57733(8) 0.0219(8) Uani 1 1 d . . .
H3A H 0.4743 0.6684 0.5648 0.033 Uiso 1 1 calc R . .
C6 C 0.3035(10) 0.4634(6) 0.61851(12) 0.0191(11) Uani 1 1 d . . .
H6 H 0.4375 0.3880 0.6151 0.023 Uiso 1 1 calc R . .
Cl2 Cl 0.0122(3) 0.37380(14) 0.63121(3) 0.0221(3) Uani 1 1 d . . .
C7 C 0.4030(11) 0.5627(5) 0.64552(13) 0.0200(11) Uani 1 1 d . . .
H7 H 0.5717 0.6026 0.6379 0.024 Uiso 1 1 calc R . .
Cl3 Cl 0.1788(3) 0.71217(14) 0.65005(3) 0.0250(3) Uani 1 1 d . . .
C8 C 0.4476(10) 0.4927(6) 0.67839(13) 0.0214(11) Uani 1 1 d . . .
H8A H 0.5426 0.4022 0.6749 0.026 Uiso 1 1 calc R . .
H8B H 0.2786 0.4686 0.6883 0.026 Uiso 1 1 calc R . .
C9 C 0.5986(12) 0.5853(6) 0.70259(13) 0.0228(12) Uani 1 1 d . . .
H9A H 0.7398 0.6341 0.6907 0.027 Uiso 1 1 calc R . .
H9B H 0.4827 0.6596 0.7116 0.027 Uiso 1 1 calc R . .
C10 C 0.7120(11) 0.4996(6) 0.73076(12) 0.0211(11) Uani 1 1 d . . .
H10A H 0.8139 0.4195 0.7216 0.025 Uiso 1 1 calc R . .
H10B H 0.5696 0.4583 0.7439 0.025 Uiso 1 1 calc R . .
C11 C 0.8843(11) 0.5879(6) 0.75335(13) 0.0214(12) Uani 1 1 d . . .
H11A H 0.7778 0.6614 0.7644 0.026 Uiso 1 1 calc R . .
H11B H 1.0148 0.6381 0.7398 0.026 Uiso 1 1 calc R . .
C12 C 1.0225(11) 0.4996(6) 0.77950(12) 0.0201(11) Uani 1 1 d . . .
H12A H 0.8918 0.4526 0.7936 0.024 Uiso 1 1 calc R . .
H12B H 1.1231 0.4236 0.7685 0.024 Uiso 1 1 calc R . .
C13 C 1.2020(11) 0.5856(6) 0.80117(13) 0.0208(11) Uani 1 1 d . . .
H13A H 1.1015 0.6610 0.8124 0.025 Uiso 1 1 calc R . .
H13B H 1.3323 0.6332 0.7872 0.025 Uiso 1 1 calc R . .
C14 C 1.3396(12) 0.4958(6) 0.82683(13) 0.0246(12) Uani 1 1 d . . .
H14A H 1.4393 0.4202 0.8155 0.029 Uiso 1 1 calc R . .
H14B H 1.2092 0.4485 0.8409 0.029 Uiso 1 1 calc R . .
C15 C 1.5217(12) 0.5816(6) 0.84867(14) 0.0268(12) Uani 1 1 d . . .
H15A H 1.6480 0.6316 0.8349 0.040 Uiso 1 1 calc R . .
H15B H 1.6118 0.5168 0.8637 0.040 Uiso 1 1 calc R . .
H15C H 1.4225 0.6514 0.8614 0.040 Uiso 1 1 calc R . .
C16 C -0.4446(11) 0.6085(6) 0.43653(13) 0.0243(12) Uani 1 1 d . . .
H16A H -0.2914 0.6284 0.4227 0.029 Uiso 1 1 calc R . .
H16B H -0.5353 0.6996 0.4408 0.029 Uiso 1 1 calc R . .
C17 C -0.6206(12) 0.5054(7) 0.41935(14) 0.0292(13) Uani 1 1 d . . .
H17A H -0.5295 0.4152 0.4156 0.044 Uiso 1 1 calc R . .
H17B H -0.6746 0.5459 0.3982 0.044 Uiso 1 1 calc R . .
H17C H -0.7728 0.4879 0.4330 0.044 Uiso 1 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
C1 O1 1.204(7) . ?
C1 O2 1.345(7) . ?
C1 C2 1.480(7) . ?
O2 C16 1.447(6) . ?
C2 C3 1.319(8) . ?
C2 H2 0.9500 . ?
C3 C4 1.498(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.532(8) . ?
C4 Cl1 1.825(6) . ?
C4 H4 1.0000 . ?
C5 O3 1.427(6) . ?
C5 C6 1.515(7) . ?
C5 H5 1.0000 . ?
O3 H3A 0.8400 . ?
C6 C7 1.529(7) . ?
C6 Cl2 1.803(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.507(7) . ?
C7 Cl3 1.829(5) . ?
C7 H7 1.0000 . ?
C8 C9 1.527(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.517(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.525(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.526(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.514(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.525(8) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.501(8) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
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
O1 C1 O2 124.2(5) . . ?
O1 C1 C2 126.4(5) . . ?
O2 C1 C2 109.4(5) . . ?
C1 O2 C16 117.9(4) . . ?
C3 C2 C1 121.5(5) . . ?
C3 C2 H2 119.2 . . ?
C1 C2 H2 119.2 . . ?
C2 C3 C4 120.5(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 111.5(5) . . ?
C3 C4 Cl1 109.0(4) . . ?
C5 C4 Cl1 110.2(4) . . ?
C3 C4 H4 108.7 . . ?
C5 C4 H4 108.7 . . ?
Cl1 C4 H4 108.7 . . ?
O3 C5 C6 104.9(4) . . ?
O3 C5 C4 111.9(4) . . ?
C6 C5 C4 114.2(4) . . ?
O3 C5 H5 108.6 . . ?
C6 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
C5 O3 H3A 109.5 . . ?
C5 C6 C7 115.0(4) . . ?
C5 C6 Cl2 109.2(4) . . ?
C7 C6 Cl2 111.1(4) . . ?
C5 C6 H6 107.1 . . ?
C7 C6 H6 107.1 . . ?
Cl2 C6 H6 107.1 . . ?
C8 C7 C6 115.1(4) . . ?
C8 C7 Cl3 109.9(4) . . ?
C6 C7 Cl3 108.9(4) . . ?
C8 C7 H7 107.5 . . ?
C6 C7 H7 107.5 . . ?
Cl3 C7 H7 107.5 . . ?
C7 C8 C9 113.8(5) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 112.6(4) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 C11 113.3(5) . . ?
C9 C10 H10A 108.9 . . ?
C11 C10 H10A 108.9 . . ?
C9 C10 H10B 108.9 . . ?
C11 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
C10 C11 C12 113.6(4) . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11B 108.8 . . ?
C12 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 114.0(4) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 113.3(4) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 113.6(5) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 C17 107.4(5) . . ?
O2 C16 H16A 110.2 . . ?
C17 C16 H16A 110.2 . . ?
O2 C16 H16B 110.2 . . ?
C17 C16 H16B 110.2 . . ?
H16A C16 H16B 108.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 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
O1 C1 O2 C16 1.5(8) . . . . ?
C2 C1 O2 C16 -178.7(4) . . . . ?
O1 C1 C2 C3 -16.9(9) . . . . ?
O2 C1 C2 C3 163.3(5) . . . . ?
C1 C2 C3 C4 176.1(5) . . . . ?
C2 C3 C4 C5 -121.3(6) . . . . ?
C2 C3 C4 Cl1 116.8(5) . . . . ?
C3 C4 C5 O3 -60.8(6) . . . . ?
Cl1 C4 C5 O3 60.4(5) . . . . ?
C3 C4 C5 C6 -179.7(4) . . . . ?
Cl1 C4 C5 C6 -58.5(5) . . . . ?
O3 C5 C6 C7 55.7(6) . . . . ?
C4 C5 C6 C7 178.6(5) . . . . ?
O3 C5 C6 Cl2 -178.7(3) . . . . ?
C4 C5 C6 Cl2 -55.8(5) . . . . ?
C5 C6 C7 C8 179.9(4) . . . . ?
Cl2 C6 C7 C8 55.3(5) . . . . ?
C5 C6 C7 Cl3 56.0(5) . . . . ?
Cl2 C6 C7 Cl3 -68.6(4) . . . . ?
C6 C7 C8 C9 167.8(5) . . . . ?
Cl3 C7 C8 C9 -68.8(5) . . . . ?
C7 C8 C9 C10 -162.2(5) . . . . ?
C8 C9 C10 C11 174.6(5) . . . . ?
C9 C10 C11 C12 -173.7(5) . . . . ?
C10 C11 C12 C13 177.7(5) . . . . ?
C11 C12 C13 C14 -179.5(5) . . . . ?
C12 C13 C14 C15 179.8(5) . . . . ?
C1 O2 C16 C17 158.5(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O1 0.84 1.99 2.815(5) 166.7 3_566

_diffrn_measured_fraction_theta_max 0.977
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.530
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.094
####################################################################### 
# 
# 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_jsrsce
_database_code_depnum_ccdc_archive 'CCDC 1470484'
_audit_update_record             
;
2016-03-24 deposited with the CCDC.
2016-08-02 downloaded from the CCDC.
;
_nottingham_internal_coll_name   JSRSCE
_nottingham_internal_coll_number 12838
_nottingham_internal_coll_client JS/RD
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '20.0000, 80.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   ?
_nottingham_internal_coll_location NOTTS
_nottingham_internal_NCS_number  ?
_nottingham_internal_process_date ?
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date ?
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date ?
_nottingham_internal_refinement_user pczwl
_nottingham_internal_self_archive_date ?
_nottingham_internal_self_validation_date ?
_nottingham_internal_self_validation_user ?
_nottingham_internal_validation_date 3/2/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 5/8/2014
_refine_special_details          
'Enhanced rigid bond restraints were applied to the thermal parameters of all atoms, and similarity restraints were applied to the thermal parameters of atoms C9-C13.'
_vrf_PLAT340_jsrsce              
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0208 Ang.  
RESPONSE: Low precision on the C-C bonds reflects the relatively low quality data.
;
_audit_creation_date             2014-08-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H28 Cl2 O4'
_chemical_formula_sum            'C15 H28 Cl2 O4'
_chemical_formula_weight         343.27
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H28 Cl2 O4'
_chemical_oxdiff_usercomment     
'JSRSCE #12838 IN FOMBLIN FILM ON MICROMOUNT FOR JS/RS'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.5540(6)
_cell_length_b                   8.7336(10)
_cell_length_c                   36.980(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1793.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3309
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.0110
_cell_measurement_theta_min      4.8790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.359
_exptl_absorpt_correction_T_max  1.348
_exptl_absorpt_correction_T_min  0.445
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.7583
_exptl_crystal_size_mid          0.0861
_exptl_crystal_size_min          0.0217
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            11721
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.388
_diffrn_reflns_theta_min         4.783
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -10.00   32.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5554    0.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega   38.00  123.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5554    0.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  3 omega  -41.00   25.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   45.0000    0.0000 66

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   98.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -45.0000 -120.0000 63

#__ type_ start__ end____ width___ exp.time_
  5 omega   31.00   86.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -30.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00  134.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -77.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   91.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -30.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
  8 omega   71.00  103.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -94.0000  -90.0000 32

#__ type_ start__ end____ width___ exp.time_
  9 omega   42.00   79.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -30.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   34.00   62.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045  -37.0000   70.0000 28

#__ type_ start__ end____ width___ exp.time_
 11 omega   17.00  109.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5554   38.0000   90.0000 92

#__ type_ start__ end____ width___ exp.time_
 12 omega   12.00  106.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       37.5554   57.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
 13 omega   79.00  173.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045   61.0000   30.0000 94

#__ type_ start__ end____ width___ exp.time_
 14 omega   64.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045   15.0000  -30.0000 114

#__ type_ start__ end____ width___ exp.time_
 15 omega   84.00  172.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045   30.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 16 omega   84.00  178.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      104.7045   30.0000  120.0000 94
;
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.2523981000
_diffrn_orient_matrix_UB_12      -0.0714681000
_diffrn_orient_matrix_UB_13      -0.0033900000
_diffrn_orient_matrix_UB_21      -0.0080233000
_diffrn_orient_matrix_UB_22      0.0448422000
_diffrn_orient_matrix_UB_23      -0.0402267000
_diffrn_orient_matrix_UB_31      0.1146764000
_diffrn_orient_matrix_UB_32      -0.1550939000
_diffrn_orient_matrix_UB_33      -0.0101532000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.665
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                3031
_reflns_number_total             3611
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         1.446
_refine_diff_density_min         -0.746
_refine_diff_density_rms         0.144
_refine_ls_abs_structure_details 
;
 Flack x determined using 1007 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     168
_refine_ls_R_factor_all          0.1504
_refine_ls_R_factor_gt           0.1349
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0905P)²+22.9016P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3369
_refine_ls_wR_factor_ref         0.3452
_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, All O(H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C12 \\sim C11 \\sim C10 \\sim C9 \\sim C8 \\sim C7: within 2A with
sigma of 0.005 and sigma for terminal atoms of 0.01
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,
 H11B), C12(H12A,H12B), C14(H14A,H14B)
4.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
4.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
Cl1 Cl 0.8502(7) 0.3127(4) 0.40303(10) 0.0486(9) Uani 1 1 d . . . . .
C1 C 0.842(3) 0.524(2) 0.5134(5) 0.051(3) Uani 1 1 d . . . . .
O1 O 0.9105(19) 0.6542(14) 0.5104(3) 0.057(3) Uani 1 1 d . . . . .
C2 C 0.808(3) 0.4215(17) 0.4810(4) 0.043(3) Uani 1 1 d . . . . .
H2 H 0.9675 0.4089 0.4688 0.051 Uiso 1 1 calc R . . . .
Cl2 Cl 0.6304(7) 0.6514(4) 0.37726(10) 0.0465(9) Uani 1 1 d . . . . .
O2 O 0.799(2) 0.4522(15) 0.5445(3) 0.058(3) Uani 1 1 d . . . . .
O3 O 0.7178(17) 0.2717(12) 0.4898(3) 0.047(3) Uani 1 1 d . . . . .
H3 H 0.5683 0.2692 0.4864 0.070 Uiso 1 1 calc GR . . . .
C3 C 0.638(3) 0.5005(18) 0.4546(4) 0.043(3) Uani 1 1 d . . . . .
H3A H 0.7098 0.5997 0.4464 0.051 Uiso 1 1 calc R . . . .
C4 C 0.578(2) 0.3969(16) 0.4210(4) 0.038(3) Uani 1 1 d . . . . .
H4 H 0.4685 0.3126 0.4291 0.046 Uiso 1 1 calc R . . . .
O4 O 0.410(2) 0.5267(14) 0.4711(3) 0.049(3) Uani 1 1 d . . . . .
H4A H 0.4304 0.5498 0.4930 0.074 Uiso 1 1 calc GR . . . .
C5 C 0.449(2) 0.4901(16) 0.3919(4) 0.038(3) Uani 1 1 d . . . . .
H5 H 0.2978 0.5317 0.4027 0.046 Uiso 1 1 calc R . . . .
C6 C 0.380(3) 0.3962(15) 0.3587(4) 0.040(3) Uani 1 1 d . . . . .
H6A H 0.2968 0.3015 0.3665 0.049 Uiso 1 1 calc R . . . .
H6B H 0.5272 0.3661 0.3454 0.049 Uiso 1 1 calc R . . . .
C7 C 0.214(2) 0.4871(15) 0.3334(4) 0.038(2) Uani 1 1 d . . . . .
H7A H 0.0925 0.5416 0.3482 0.046 Uiso 1 1 calc R . . . .
H7B H 0.3111 0.5653 0.3206 0.046 Uiso 1 1 calc R . . . .
C8 C 0.085(3) 0.3907(15) 0.3056(4) 0.037(2) Uani 1 1 d . . . . .
H8A H 0.2053 0.3389 0.2902 0.045 Uiso 1 1 calc R . . . .
H8B H -0.0095 0.3105 0.3182 0.045 Uiso 1 1 calc R . . . .
C9 C -0.080(3) 0.4819(14) 0.2822(4) 0.037(2) Uani 1 1 d . . . . .
H9A H 0.0170 0.5584 0.2689 0.044 Uiso 1 1 calc R . . . .
H9B H -0.1927 0.5390 0.2980 0.044 Uiso 1 1 calc R . . . .
C10 C -0.228(3) 0.3919(15) 0.2550(4) 0.039(2) Uani 1 1 d . . . . .
H10A H -0.1152 0.3388 0.2384 0.046 Uiso 1 1 calc R . . . .
H10B H -0.3190 0.3121 0.2682 0.046 Uiso 1 1 calc R . . . .
C11 C -0.402(3) 0.4834(15) 0.2326(4) 0.040(2) Uani 1 1 d . . . . .
H11A H -0.3116 0.5641 0.2196 0.049 Uiso 1 1 calc R . . . .
H11B H -0.5167 0.5350 0.2491 0.049 Uiso 1 1 calc R . . . .
C12 C -0.545(3) 0.3909(15) 0.2050(4) 0.044(3) Uani 1 1 d . . . . .
H12A H -0.4306 0.3398 0.1885 0.052 Uiso 1 1 calc R . . . .
H12B H -0.6349 0.3098 0.2180 0.052 Uiso 1 1 calc R . . . .
C13 C -0.719(3) 0.4807(19) 0.1830(5) 0.054(4) Uani 1 1 d . . . . .
H13A H -0.7964 0.4132 0.1654 0.081 Uiso 1 1 calc GR . . . .
H13B H -0.6331 0.5627 0.1703 0.081 Uiso 1 1 calc GR . . . .
H13C H -0.8414 0.5254 0.1989 0.081 Uiso 1 1 calc GR . . . .
C14 C 0.826(4) 0.536(3) 0.5778(5) 0.070(5) Uani 1 1 d . . . . .
H14A H 0.8630 0.4647 0.5978 0.084 Uiso 1 1 calc R . . . .
H14B H 0.9616 0.6093 0.5756 0.084 Uiso 1 1 calc R . . . .
C15 C 0.609(3) 0.619(2) 0.5861(7) 0.090(7) Uani 1 1 d . . . . .
H15A H 0.5420 0.6623 0.5638 0.134 Uiso 1 1 calc GR . . . .
H15B H 0.6456 0.7018 0.6031 0.134 Uiso 1 1 calc GR . . . .
H15C H 0.4916 0.5491 0.5970 0.134 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C4 1.808(14) . ?
C1 O1 1.21(2) . ?
C1 C2 1.51(2) . ?
C1 O2 1.33(2) . ?
C2 H2 1.0000 . ?
C2 O3 1.439(17) . ?
C2 C3 1.52(2) . ?
Cl2 C5 1.813(14) . ?
O2 C14 1.44(2) . ?
O3 H3 0.8400 . ?
C3 H3A 1.0000 . ?
C3 C4 1.57(2) . ?
C3 O4 1.425(17) . ?
C4 H4 1.0000 . ?
C4 C5 1.528(19) . ?
O4 H4A 0.8400 . ?
C5 H5 1.0000 . ?
C5 C6 1.526(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.535(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.510(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.491(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.517(19) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.505(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.52(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.48(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.44(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
O1 C1 C2 121.6(16) . . ?
O1 C1 O2 125.5(16) . . ?
O2 C1 C2 112.8(15) . . ?
C1 C2 H2 108.1 . . ?
C1 C2 C3 108.7(13) . . ?
O3 C2 C1 113.6(13) . . ?
O3 C2 H2 108.1 . . ?
O3 C2 C3 110.1(12) . . ?
C3 C2 H2 108.1 . . ?
C1 O2 C14 118.7(16) . . ?
C2 O3 H3 109.5 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 C4 112.2(12) . . ?
C4 C3 H3A 110.1 . . ?
O4 C3 C2 110.4(12) . . ?
O4 C3 H3A 110.1 . . ?
O4 C3 C4 103.9(11) . . ?
Cl1 C4 H4 108.6 . . ?
C3 C4 Cl1 110.2(9) . . ?
C3 C4 H4 108.6 . . ?
C5 C4 Cl1 110.3(10) . . ?
C5 C4 C3 110.5(11) . . ?
C5 C4 H4 108.6 . . ?
C3 O4 H4A 109.5 . . ?
Cl2 C5 H5 107.7 . . ?
C4 C5 Cl2 111.4(9) . . ?
C4 C5 H5 107.7 . . ?
C6 C5 Cl2 108.6(10) . . ?
C6 C5 C4 113.5(12) . . ?
C6 C5 H5 107.7 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.4(11) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.3(11) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 C7 112.9(11) . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
C8 C9 C10 116.1(11) . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C11 C10 C9 115.9(11) . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C10 C11 H11A 108.5 . . ?
C10 C11 H11B 108.5 . . ?
C10 C11 C12 115.0(11) . . ?
H11A C11 H11B 107.5 . . ?
C12 C11 H11A 108.5 . . ?
C12 C11 H11B 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 115.2(12) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C15 C14 O2 110.6(17) . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O3 0.84 2.17 2.902(7) 146.3 3_456
O3 H3 O4 0.84 2.48 2.890(16) 111.1 .
O4 H4A O1 0.84 2.59 2.869(17) 100.9 3_466

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
Cl1 C4 C5 Cl2 -63.9(11) . . . . ?
Cl1 C4 C5 C6 59.1(14) . . . . ?
C1 C2 C3 C4 -176.0(12) . . . . ?
C1 C2 C3 O4 -60.6(16) . . . . ?
C1 O2 C14 C15 85(2) . . . . ?
O1 C1 C2 O3 -177.9(13) . . . . ?
O1 C1 C2 C3 -55.0(19) . . . . ?
O1 C1 O2 C14 2(2) . . . . ?
C2 C1 O2 C14 179.8(14) . . . . ?
C2 C3 C4 Cl1 -46.7(14) . . . . ?
C2 C3 C4 C5 -168.9(12) . . . . ?
Cl2 C5 C6 C7 -65.4(13) . . . . ?
O2 C1 C2 O3 4.5(18) . . . . ?
O2 C1 C2 C3 127.4(14) . . . . ?
O3 C2 C3 C4 -51.0(16) . . . . ?
O3 C2 C3 O4 64.4(15) . . . . ?
C3 C4 C5 Cl2 58.3(13) . . . . ?
C3 C4 C5 C6 -178.8(11) . . . . ?
C4 C5 C6 C7 170.1(11) . . . . ?
O4 C3 C4 Cl1 -165.9(9) . . . . ?
O4 C3 C4 C5 71.9(14) . . . . ?
C5 C6 C7 C8 -164.4(12) . . . . ?
C6 C7 C8 C9 178.3(12) . . . . ?
C7 C8 C9 C10 -176.7(12) . . . . ?
C8 C9 C10 C11 177.3(13) . . . . ?
C9 C10 C11 C12 179.1(13) . . . . ?
C10 C11 C12 C13 179.7(14) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -6 -6 0.0429 0.0031 -5.9859 -5.9936 0.4473 -0.0273 0.9896
0 6 6 0.0359 -0.0031 5.9859 5.9936 -0.4473 0.0273 -0.9896
-4 0 1 0.3848 -4.0069 -0.0020 0.9755 1.0082 -0.0072 -0.4691
4 0 -1 0.3719 4.0069 0.0020 -0.9755 -1.0082 0.0072 0.4691
0 0 -1 0.0143 0.0007 0.0009 -1.0008 0.0032 0.0403 0.0101
0 0 1 0.0073 -0.0007 -0.0009 1.0008 -0.0032 -0.0403 -0.0101

_olex2_exptl_crystal_mounting_method 'mounted in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
