# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_DM_279
_database_code_depnum_ccdc_archive 'CCDC 2091913'
loop_
_audit_author_name
_audit_author_address
'Antoine de Gombert'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The H atoms were all located in a difference map, but were 
repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98 Å) 
and 
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom), 
after which the positions were refined with riding constraints 
(Cooper et al, 2010). 
 
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 
43, 1100-1107. 

PLAT915_ALERT_3_B No Flack x Check Done: Low Friedel Pair Coverage
The absolute structure was confirmed by analysis of Friedel pairs

;

_cell_length_a                   7.6588(4)
_cell_length_b                   7.9714(3)
_cell_length_c                   12.8907(5)
_cell_angle_alpha                99.211(3)
_cell_angle_beta                 90.731(4)
_cell_angle_gamma                99.142(4)
_cell_volume                     766.39(6)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P 1 '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C8 H9.50 N0.50 O1.50 S0.50 
# Dc =      0.66 Fooo =    162.00 Mu =      1.10 M =    152.70
# Found Formula = C16 H19.00 N1 O3 S1 
# Dc =      1.32 FOOO =    324.00 Mu =      2.21 M =    305.40

_chemical_formula_sum            'C16 H19.00 N1 O3 S1'
_chemical_formula_moiety         'C16 H19.00 N1 O3 S1'
_chemical_compound_source        .
_chemical_formula_weight         305.40


_cell_measurement_reflns_used    4134
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      29.37
_cell_measurement_temperature    170

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             323.998
_exptl_absorpt_coefficient_mu    0.221

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      170
_diffrn_reflns_number            11856
_diffrn_reflns_av_unetI/netI     0.066
_reflns_number_total             6508
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 6508 
# Number of reflections with Friedels Law is 4405 
# Theoretical number of reflections is about 4737 


_diffrn_reflns_theta_min         2.624
_diffrn_reflns_theta_max         30.646
_diffrn_measured_fraction_theta_max 0.930

_diffrn_reflns_theta_full        25.130
_diffrn_measured_fraction_theta_full 0.977


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -9
_reflns_limit_h_max              10
_reflns_limit_k_min              -11
_reflns_limit_k_max              10
_reflns_limit_l_min              -18
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   2.42
_oxford_diffrn_Wilson_scale      0.34

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.48
_refine_diff_density_max         0.48


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     3
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6507
_oxford_refine_ls_R_factor_ref   0.0718
_refine_ls_R_factor_all          0.0718
_refine_ls_wR_factor_ref         0.1129
_refine_ls_wR_factor_all         0.1129
_refine_ls_goodness_of_fit_ref   0.9580
_refine_ls_shift/su_max          0.0356472
_refine_ls_shift/su_mean         0.0023167


# Computed with I/sigma = -10 
_oxford_reflns_number_all        6507
_oxford_refine_ls_R_factor_all   0.0718
_oxford_refine_ls_wR_factor_all  0.1129

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4725
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_gt          0.0989

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0.09(4) # for 1354 Friedel pairs 
_oxford_Bijvoet_difference       0.04(4) # for 1354 Friedel pairs 
# (Similar to the Parsons(q).) 
_refine_ls_abs_structure_Flack   0.04(4)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1354 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.49967(13) 0.50009(12) 0.49998(7) 0.0364 1.0000 Uani . . . . . .
C2 C 0.5339(4) 0.3044(4) 0.5376(2) 0.0301 1.0000 Uani . . . . . .
C3 C 0.5617(4) 0.2923(4) 0.6452(2) 0.0249 1.0000 Uani . . . . . .
C4 C 0.5653(4) 0.4448(4) 0.7294(2) 0.0270 1.0000 Uani . . . . . .
O5 O 0.5200(4) 0.5760(3) 0.70838(17) 0.0498 1.0000 Uani . . . . . .
C6 C 0.6297(4) 0.4360(4) 0.8391(2) 0.0291 1.0000 Uani . . . . . .
C7 C 0.5997(4) 0.5870(3) 0.9208(2) 0.0256 1.0000 Uani . . . . . .
O8 O 0.6353(3) 0.5358(3) 1.02087(15) 0.0357 1.0000 Uani . . . . . .
C9 C 0.6016(5) 0.6616(4) 1.1076(2) 0.0365 1.0000 Uani . . . . . .
C10 C 0.7195(4) 0.8326(4) 1.1077(2) 0.0292 1.0000 Uani . . . . . .
N11 N 0.7020(3) 0.8815(3) 1.00421(17) 0.0282 1.0000 Uani . . . . . .
C12 C 0.7209(4) 0.7536(4) 0.9126(2) 0.0283 1.0000 Uani . . . . . .
C13 C 0.6207(4) 1.0187(4) 1.0023(2) 0.0281 1.0000 Uani . . . . . .
O14 O 0.5798(3) 1.0703(3) 0.92191(16) 0.0355 1.0000 Uani . . . . . .
C15 C 0.5917(4) 1.0969(4) 1.1145(2) 0.0362 1.0000 Uani . . . . . .
C16 C 0.6643(5) 0.9832(4) 1.1839(2) 0.0390 1.0000 Uani . . . . . .
C17 C 0.5884(4) 0.1344(4) 0.6725(2) 0.0294 1.0000 Uani . . . . . .
C18 C 0.5897(5) -0.0101(4) 0.5968(2) 0.0400 1.0000 Uani . . . . . .
C19 C 0.5659(5) 0.0045(4) 0.4922(3) 0.0487 1.0000 Uani . . . . . .
C20 C 0.5379(5) 0.1571(4) 0.4632(2) 0.0402 1.0000 Uani . . . . . .
C21 C 0.4904(5) 0.4496(5) 0.3575(3) 0.0481 1.0000 Uani . . . . . .
S22 S -0.00885(14) 0.37613(13) 1.40346(7) 0.0422 1.0000 Uani . . . . . .
C23 C -0.0097(5) 0.4288(5) 1.5446(3) 0.0524 1.0000 Uani . . . . . .
C24 C 0.0438(4) 0.5818(4) 1.3658(2) 0.0343 1.0000 Uani . . . . . .
C25 C 0.0720(4) 0.5970(4) 1.2584(2) 0.0282 1.0000 Uani . . . . . .
C26 C 0.0502(4) 0.4431(4) 1.1747(2) 0.0289 1.0000 Uani . . . . . .
O27 O 0.0079(4) 0.2981(3) 1.19691(18) 0.0488 1.0000 Uani . . . . . .
C28 C 0.0745(4) 0.4678(4) 1.0622(2) 0.0290 1.0000 Uani . . . . . .
C29 C 0.0493(4) 0.3010(4) 0.9845(2) 0.0275 1.0000 Uani . . . . . .
O30 O 0.0594(3) 0.3498(3) 0.88143(15) 0.0355 1.0000 Uani . . . . . .
C31 C 0.0231(5) 0.2007(4) 0.8005(2) 0.0392 1.0000 Uani . . . . . .
C32 C 0.1635(4) 0.0874(4) 0.8048(2) 0.0296 1.0000 Uani . . . . . .
N33 N 0.1718(3) 0.0481(3) 0.91071(18) 0.0265 1.0000 Uani . . . . . .
C34 C 0.1881(4) 0.1887(4) 0.9983(2) 0.0281 1.0000 Uani . . . . . .
C35 C 0.2027(4) -0.1114(4) 0.9153(2) 0.0292 1.0000 Uani . . . . . .
O36 O 0.2307(3) -0.1681(3) 0.99663(17) 0.0381 1.0000 Uani . . . . . .
C37 C 0.1988(4) -0.2080(4) 0.8036(2) 0.0392 1.0000 Uani . . . . . .
C38 C 0.1255(4) -0.0905(4) 0.7365(2) 0.0393 1.0000 Uani . . . . . .
C39 C 0.1181(4) 0.7610(4) 1.2317(2) 0.0314 1.0000 Uani . . . . . .
C40 C 0.1312(5) 0.9091(4) 1.3063(3) 0.0441 1.0000 Uani . . . . . .
C41 C 0.0992(6) 0.8914(5) 1.4093(3) 0.0581 1.0000 Uani . . . . . .
C42 C 0.0572(5) 0.7318(5) 1.4384(3) 0.0506 1.0000 Uani . . . . . .
H61 H 0.5653 0.3327 0.8584 0.0396 1.0000 Uiso . . . . . .
H62 H 0.7606 0.4281 0.8409 0.0391 1.0000 Uiso . . . . . .
H71 H 0.4730 0.6009 0.9196 0.0338 1.0000 Uiso . . . . . .
H92 H 0.4782 0.6846 1.1006 0.0446 1.0000 Uiso . . . . . .
H91 H 0.6221 0.6166 1.1739 0.0455 1.0000 Uiso . . . . . .
H101 H 0.8452 0.8190 1.1161 0.0357 1.0000 Uiso . . . . . .
H121 H 0.6932 0.7998 0.8465 0.0345 1.0000 Uiso . . . . . .
H122 H 0.8431 0.7299 0.9125 0.0342 1.0000 Uiso . . . . . .
H151 H 0.6664 1.2094 1.1277 0.0473 1.0000 Uiso . . . . . .
H152 H 0.4644 1.1014 1.1205 0.0468 1.0000 Uiso . . . . . .
H162 H 0.7670 1.0553 1.2258 0.0499 1.0000 Uiso . . . . . .
H161 H 0.5697 0.9415 1.2285 0.0495 1.0000 Uiso . . . . . .
H171 H 0.6114 0.1241 0.7458 0.0363 1.0000 Uiso . . . . . .
H181 H 0.6124 -0.1165 0.6169 0.0516 1.0000 Uiso . . . . . .
H191 H 0.5733 -0.0914 0.4386 0.0553 1.0000 Uiso . . . . . .
H201 H 0.5217 0.1645 0.3923 0.0451 1.0000 Uiso . . . . . .
H212 H 0.4795 0.5529 0.3294 0.0770 1.0000 Uiso . . . . . .
H211 H 0.3834 0.3677 0.3358 0.0777 1.0000 Uiso . . . . . .
H213 H 0.5963 0.4000 0.3365 0.0777 1.0000 Uiso . . . . . .
H231 H -0.0245 0.3236 1.5728 0.0751 1.0000 Uiso . . . . . .
H233 H -0.1010 0.4877 1.5678 0.0732 1.0000 Uiso . . . . . .
H232 H 0.0999 0.5047 1.5708 0.0739 1.0000 Uiso . . . . . .
H282 H -0.0114 0.5349 1.0399 0.0394 1.0000 Uiso . . . . . .
H281 H 0.1917 0.5314 1.0557 0.0392 1.0000 Uiso . . . . . .
H291 H -0.0687 0.2337 0.9875 0.0345 1.0000 Uiso . . . . . .
H311 H 0.0201 0.2397 0.7312 0.0470 1.0000 Uiso . . . . . .
H312 H -0.0906 0.1348 0.8127 0.0468 1.0000 Uiso . . . . . .
H321 H 0.2795 0.1557 0.7934 0.0369 1.0000 Uiso . . . . . .
H341 H 0.3033 0.2582 0.9962 0.0352 1.0000 Uiso . . . . . .
H342 H 0.1752 0.1378 1.0638 0.0349 1.0000 Uiso . . . . . .
H371 H 0.1211 -0.3210 0.7968 0.0482 1.0000 Uiso . . . . . .
H372 H 0.3197 -0.2250 0.7825 0.0468 1.0000 Uiso . . . . . .
H381 H 0.1846 -0.0911 0.6695 0.0490 1.0000 Uiso . . . . . .
H382 H 0.0028 -0.1283 0.7236 0.0500 1.0000 Uiso . . . . . .
H391 H 0.1412 0.7702 1.1610 0.0392 1.0000 Uiso . . . . . .
H401 H 0.1587 1.0204 1.2838 0.0537 1.0000 Uiso . . . . . .
H411 H 0.1062 0.9913 1.4605 0.0676 1.0000 Uiso . . . . . .
H421 H 0.0281 0.7276 1.5080 0.0571 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.305(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.762(3) yes
S1 . C21 . 1.814(3) yes
C2 . C3 . 1.422(4) yes
C2 . C20 . 1.397(4) yes
C3 . C4 . 1.491(4) yes
C3 . C17 . 1.404(4) yes
C4 . O5 . 1.221(4) yes
C4 . C6 . 1.508(4) yes
C6 . C7 . 1.516(4) yes
C6 . H61 . 0.960 no
C6 . H62 . 1.015 no
C7 . O8 . 1.449(3) yes
C7 . C12 . 1.514(4) yes
C7 . H71 . 0.994 no
O8 . C9 . 1.433(3) yes
C9 . C10 . 1.511(4) yes
C9 . H92 . 0.997 no
C9 . H91 . 0.998 no
C10 . N11 . 1.459(3) yes
C10 . C16 . 1.543(4) yes
C10 . H101 . 0.992 no
N11 . C12 . 1.456(3) yes
N11 . C13 . 1.345(4) yes
C12 . H121 . 1.014 no
C12 . H122 . 0.984 no
C13 . O14 . 1.230(3) yes
C13 . C15 . 1.514(4) yes
C15 . C16 . 1.528(4) yes
C15 . H151 . 0.973 no
C15 . H152 . 0.985 no
C16 . H162 . 0.993 no
C16 . H161 . 0.980 no
C17 . C18 . 1.387(4) yes
C17 . H171 . 0.978 no
C18 . C19 . 1.384(4) yes
C18 . H181 . 0.966 no
C19 . C20 . 1.376(5) yes
C19 . H191 . 0.955 no
C20 . H201 . 0.933 no
C21 . H212 . 0.966 no
C21 . H211 . 0.971 no
C21 . H213 . 0.980 no
S22 . C23 . 1.801(3) yes
S22 . C24 . 1.771(3) yes
C23 . H231 . 0.958 no
C23 . H233 . 0.930 no
C23 . H232 . 0.975 no
C24 . C25 . 1.424(4) yes
C24 . C42 . 1.384(4) yes
C25 . C26 . 1.485(4) yes
C25 . C39 . 1.397(4) yes
C26 . O27 . 1.229(4) yes
C26 . C28 . 1.504(4) yes
C28 . C29 . 1.516(4) yes
C28 . H282 . 0.979 no
C28 . H281 . 0.970 no
C29 . O30 . 1.442(3) yes
C29 . C34 . 1.521(4) yes
C29 . H291 . 0.980 no
O30 . C31 . 1.439(4) yes
C31 . C32 . 1.516(4) yes
C31 . H311 . 0.993 no
C31 . H312 . 0.971 no
C32 . N33 . 1.452(3) yes
C32 . C38 . 1.527(4) yes
C32 . H321 . 0.992 no
N33 . C34 . 1.447(4) yes
N33 . C35 . 1.340(4) yes
C34 . H341 . 0.968 no
C34 . H342 . 0.992 no
C35 . O36 . 1.235(3) yes
C35 . C37 . 1.518(4) yes
C37 . C38 . 1.534(5) yes
C37 . H371 . 0.988 no
C37 . H372 . 0.992 no
C38 . H381 . 0.980 no
C38 . H382 . 0.944 no
C39 . C40 . 1.387(4) yes
C39 . H391 . 0.943 no
C40 . C41 . 1.379(5) yes
C40 . H401 . 0.970 no
C41 . C42 . 1.375(5) yes
C41 . H411 . 0.944 no
C42 . H421 . 0.932 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C21 . 102.69(16) yes
S1 . C2 . C3 . 120.8(2) yes
S1 . C2 . C20 . 121.5(2) yes
C3 . C2 . C20 . 117.7(3) yes
C2 . C3 . C4 . 121.1(3) yes
C2 . C3 . C17 . 119.4(3) yes
C4 . C3 . C17 . 119.5(2) yes
C3 . C4 . O5 . 119.9(3) yes
C3 . C4 . C6 . 119.2(3) yes
O5 . C4 . C6 . 120.9(3) yes
C4 . C6 . C7 . 114.0(2) yes
C4 . C6 . H61 . 107.0 no
C7 . C6 . H61 . 108.1 no
C4 . C6 . H62 . 110.8 no
C7 . C6 . H62 . 108.3 no
H61 . C6 . H62 . 108.5 no
C6 . C7 . O8 . 104.7(2) yes
C6 . C7 . C12 . 113.9(2) yes
O8 . C7 . C12 . 109.1(2) yes
C6 . C7 . H71 . 110.5 no
O8 . C7 . H71 . 106.3 no
C12 . C7 . H71 . 111.8 no
C7 . O8 . C9 . 111.7(2) yes
O8 . C9 . C10 . 111.4(2) yes
O8 . C9 . H92 . 109.6 no
C10 . C9 . H92 . 105.6 no
O8 . C9 . H91 . 108.0 no
C10 . C9 . H91 . 110.4 no
H92 . C9 . H91 . 111.8 no
C9 . C10 . N11 . 108.2(2) yes
C9 . C10 . C16 . 114.0(3) yes
N11 . C10 . C16 . 104.0(2) yes
C9 . C10 . H101 . 109.7 no
N11 . C10 . H101 . 105.7 no
C16 . C10 . H101 . 114.6 no
C10 . N11 . C12 . 117.6(2) yes
C10 . N11 . C13 . 115.0(2) yes
C12 . N11 . C13 . 124.5(2) yes
C7 . C12 . N11 . 109.3(2) yes
C7 . C12 . H121 . 111.8 no
N11 . C12 . H121 . 109.2 no
C7 . C12 . H122 . 107.5 no
N11 . C12 . H122 . 108.9 no
H121 . C12 . H122 . 110.2 no
N11 . C13 . O14 . 124.6(3) yes
N11 . C13 . C15 . 108.5(2) yes
O14 . C13 . C15 . 126.9(3) yes
C13 . C15 . C16 . 105.8(2) yes
C13 . C15 . H151 . 106.5 no
C16 . C15 . H151 . 107.7 no
C13 . C15 . H152 . 107.6 no
C16 . C15 . H152 . 114.8 no
H151 . C15 . H152 . 113.8 no
C10 . C16 . C15 . 105.9(2) yes
C10 . C16 . H162 . 112.0 no
C15 . C16 . H162 . 107.0 no
C10 . C16 . H161 . 111.0 no
C15 . C16 . H161 . 108.4 no
H162 . C16 . H161 . 112.2 no
C3 . C17 . C18 . 121.5(3) yes
C3 . C17 . H171 . 120.8 no
C18 . C17 . H171 . 117.7 no
C17 . C18 . C19 . 118.4(3) yes
C17 . C18 . H181 . 120.4 no
C19 . C18 . H181 . 121.1 no
C18 . C19 . C20 . 121.3(3) yes
C18 . C19 . H191 . 119.8 no
C20 . C19 . H191 . 118.8 no
C2 . C20 . C19 . 121.6(3) yes
C2 . C20 . H201 . 118.2 no
C19 . C20 . H201 . 120.2 no
S1 . C21 . H212 . 108.7 no
S1 . C21 . H211 . 108.1 no
H212 . C21 . H211 . 107.0 no
S1 . C21 . H213 . 107.4 no
H212 . C21 . H213 . 114.3 no
H211 . C21 . H213 . 111.2 no
C23 . S22 . C24 . 102.26(17) yes
S22 . C23 . H231 . 108.2 no
S22 . C23 . H233 . 112.9 no
H231 . C23 . H233 . 107.9 no
S22 . C23 . H232 . 109.6 no
H231 . C23 . H232 . 112.1 no
H233 . C23 . H232 . 106.2 no
S22 . C24 . C25 . 120.4(2) yes
S22 . C24 . C42 . 121.7(3) yes
C25 . C24 . C42 . 118.0(3) yes
C24 . C25 . C26 . 121.4(3) yes
C24 . C25 . C39 . 119.0(3) yes
C26 . C25 . C39 . 119.6(3) yes
C25 . C26 . O27 . 120.3(3) yes
C25 . C26 . C28 . 119.0(3) yes
O27 . C26 . C28 . 120.6(3) yes
C26 . C28 . C29 . 113.9(2) yes
C26 . C28 . H282 . 111.0 no
C29 . C28 . H282 . 105.8 no
C26 . C28 . H281 . 109.3 no
C29 . C28 . H281 . 109.2 no
H282 . C28 . H281 . 107.5 no
C28 . C29 . O30 . 106.1(2) yes
C28 . C29 . C34 . 113.3(2) yes
O30 . C29 . C34 . 109.8(2) yes
C28 . C29 . H291 . 111.8 no
O30 . C29 . H291 . 106.5 no
C34 . C29 . H291 . 109.2 no
C29 . O30 . C31 . 110.9(2) yes
O30 . C31 . C32 . 110.2(3) yes
O30 . C31 . H311 . 108.6 no
C32 . C31 . H311 . 110.7 no
O30 . C31 . H312 . 108.6 no
C32 . C31 . H312 . 108.3 no
H311 . C31 . H312 . 110.3 no
C31 . C32 . N33 . 107.8(2) yes
C31 . C32 . C38 . 116.1(3) yes
N33 . C32 . C38 . 103.1(2) yes
C31 . C32 . H321 . 108.1 no
N33 . C32 . H321 . 106.9 no
C38 . C32 . H321 . 114.3 no
C32 . N33 . C34 . 118.5(2) yes
C32 . N33 . C35 . 114.2(2) yes
C34 . N33 . C35 . 125.6(2) yes
C29 . C34 . N33 . 109.3(2) yes
C29 . C34 . H341 . 107.7 no
N33 . C34 . H341 . 107.6 no
C29 . C34 . H342 . 112.8 no
N33 . C34 . H342 . 107.6 no
H341 . C34 . H342 . 111.8 no
N33 . C35 . O36 . 125.5(3) yes
N33 . C35 . C37 . 108.0(3) yes
O36 . C35 . C37 . 126.5(3) yes
C35 . C37 . C38 . 104.3(2) yes
C35 . C37 . H371 . 110.7 no
C38 . C37 . H371 . 111.0 no
C35 . C37 . H372 . 110.7 no
C38 . C37 . H372 . 110.4 no
H371 . C37 . H372 . 109.6 no
C37 . C38 . C32 . 103.9(2) yes
C37 . C38 . H381 . 111.4 no
C32 . C38 . H381 . 111.3 no
C37 . C38 . H382 . 109.1 no
C32 . C38 . H382 . 111.6 no
H381 . C38 . H382 . 109.5 no
C25 . C39 . C40 . 121.7(3) yes
C25 . C39 . H391 . 118.7 no
C40 . C39 . H391 . 119.6 no
C39 . C40 . C41 . 118.3(3) yes
C39 . C40 . H401 . 119.1 no
C41 . C40 . H401 . 122.6 no
C40 . C41 . C42 . 121.3(3) yes
C40 . C41 . H411 . 119.0 no
C42 . C41 . H411 . 119.7 no
C24 . C42 . C41 . 121.7(3) yes
C24 . C42 . H421 . 120.5 no
C41 . C42 . H421 . 117.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O14 1_545 147 0.96 2.38 3.230(4) yes
C6 . H62 . O30 1_655 164 1.02 2.54 3.521(4) yes
C16 . H162 . O27 1_665 136 0.99 2.53 3.318(4) yes
C17 . H171 . O14 1_545 164 0.98 2.38 3.334(4) yes
C37 . H372 . O5 1_545 148 0.99 2.47 3.356(4) yes
C39 . H391 . O36 1_565 171 0.94 2.34 3.272(4) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 -1 1 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.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_DM04_b_v2
_database_code_depnum_ccdc_archive 'CCDC 2091916'
loop_
_audit_author_name
_audit_author_address
'Antoine de Gombert'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The H atoms were all located in a difference map, but were 
repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98 Å) 
and 
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom), 
after which the positions were refined with riding constraints 
(Cooper et al, 2010). 
 
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 
43, 1100-1107. 

;

_cell_length_a                   12.2921(5)
_cell_length_b                   7.3930(3)
_cell_length_c                   15.8524(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.199(4)
_cell_angle_gamma                90
_cell_volume                     1402.54(9)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C14 H20 O3 S1 
# Dc =      1.27 Fooo =    576.00 Mu =      2.29 M =    268.38
# Found Formula = C14 H20 O3 S1 
# Dc =      1.27 FOOO =    576.00 Mu =      2.29 M =    268.38

_chemical_formula_sum            'C14 H20 O3 S1'
_chemical_formula_moiety         'C14 H20 O3 S1'
_chemical_compound_source        .
_chemical_formula_weight         268.38


_cell_measurement_reflns_used    5580
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      29.89
_cell_measurement_temperature    170

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          0.500

_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.229

# Sheldrick geometric approximatio 0.91 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      170
_diffrn_reflns_number            15714
_diffrn_reflns_av_unetI/netI     0.043
_reflns_number_total             4140
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4140 
# Theoretical number of reflections is about 8590 


_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         30.542
_diffrn_measured_fraction_theta_max 0.963

_diffrn_reflns_theta_full        25.044
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -17
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.21
_oxford_diffrn_Wilson_scale      0.17

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.36


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     2
_refine_ls_number_parameters     168
_refine_ls_number_reflns         4140
_oxford_refine_ls_R_factor_ref   0.0548
_refine_ls_R_factor_all          0.0548
_refine_ls_wR_factor_ref         0.0962
_refine_ls_wR_factor_all         0.0962
_refine_ls_goodness_of_fit_ref   0.9736
_refine_ls_shift/su_max          0.0015630
_refine_ls_shift/su_mean         0.0000827


# Computed with I/sigma = -10 
_oxford_reflns_number_all        4140
_oxford_refine_ls_R_factor_all   0.0548
_oxford_refine_ls_wR_factor_all  0.0962

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3190
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0884


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.55P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.86096(3) 0.05754(5) 0.51382(2) 0.0304 1.0000 Uani . . . . . .
C2 C 0.78204(10) 0.21150(18) 0.56130(8) 0.0237 1.0000 Uani . . . . . .
C3 C 0.72363(10) 0.34981(17) 0.50928(8) 0.0247 1.0000 Uani . . . . . .
C4 C 0.73154(10) 0.37539(18) 0.41598(8) 0.0248 1.0000 Uani . . . . . .
O5 O 0.63083(8) 0.45013(13) 0.36539(6) 0.0316 1.0000 Uani D . . . . .
C6 C 0.82727(11) 0.50472(19) 0.41190(8) 0.0283 1.0000 Uani . . . . . .
C7 C 0.84669(10) 0.52733(18) 0.32142(8) 0.0260 1.0000 Uani . . . . . .
O8 O 0.87495(8) 0.35390(13) 0.29255(6) 0.0316 1.0000 Uani . . . . . .
C9 C 0.89538(13) 0.3672(2) 0.20751(9) 0.0340 1.0000 Uani . . . . . .
C10 C 0.98988(11) 0.4965(2) 0.20529(9) 0.0308 1.0000 Uani . . . . . .
O11 O 0.96444(8) 0.67124(13) 0.23631(6) 0.0305 1.0000 Uani . . . . . .
C12 C 0.94073(12) 0.6585(2) 0.32066(8) 0.0320 1.0000 Uani . . . . . .
C13 C 1.00705(13) 0.5216(2) 0.11447(10) 0.0406 1.0000 Uani . . . . . .
C14 C 0.66037(12) 0.4707(2) 0.54611(9) 0.0337 1.0000 Uani . . . . . .
C15 C 0.65666(12) 0.4592(2) 0.63266(10) 0.0378 1.0000 Uani . . . . . .
C16 C 0.71647(12) 0.3256(2) 0.68375(9) 0.0351 1.0000 Uani . . . . . .
C17 C 0.77843(11) 0.20156(19) 0.64882(8) 0.0293 1.0000 Uani . . . . . .
C18 C 0.90286(13) -0.1126(2) 0.59557(10) 0.0390 1.0000 Uani . . . . . .
H41 H 0.7428 0.2528 0.3910 0.0281 1.0000 Uiso . . . . . .
H61 H 0.8958 0.4565 0.4511 0.0354 1.0000 Uiso . . . . . .
H62 H 0.8098 0.6207 0.4350 0.0351 1.0000 Uiso . . . . . .
H71 H 0.7811 0.5698 0.2820 0.0310 1.0000 Uiso . . . . . .
H91 H 0.9149 0.2408 0.1909 0.0424 1.0000 Uiso . . . . . .
H92 H 0.8289 0.4187 0.1694 0.0416 1.0000 Uiso . . . . . .
H101 H 1.0615 0.4651 0.2469 0.0358 1.0000 Uiso . . . . . .
H122 H 1.0122 0.6135 0.3631 0.0379 1.0000 Uiso . . . . . .
H121 H 0.9233 0.7797 0.3370 0.0394 1.0000 Uiso . . . . . .
H131 H 1.0657 0.6124 0.1169 0.0639 1.0000 Uiso . . . . . .
H133 H 1.0249 0.4085 0.0892 0.0629 1.0000 Uiso . . . . . .
H132 H 0.9411 0.5696 0.0774 0.0616 1.0000 Uiso . . . . . .
H141 H 0.6168 0.5582 0.5094 0.0405 1.0000 Uiso . . . . . .
H151 H 0.6129 0.5395 0.6573 0.0434 1.0000 Uiso . . . . . .
H161 H 0.7114 0.3099 0.7439 0.0416 1.0000 Uiso . . . . . .
H171 H 0.8235 0.1093 0.6866 0.0356 1.0000 Uiso . . . . . .
H182 H 0.9519 -0.1961 0.5746 0.0589 1.0000 Uiso . . . . . .
H183 H 0.9389 -0.0541 0.6451 0.0575 1.0000 Uiso . . . . . .
H181 H 0.8374 -0.1764 0.6085 0.0590 1.0000 Uiso . . . . . .
H51 H 0.5999(14) 0.368(2) 0.3341(11) 0.0475(19) 1.0000 Uiso D . . . . .

_refine_ls_extinction_coef       205(16)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          2.48(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.7711(13) yes
S1 . C18 . 1.7952(15) yes
C2 . C3 . 1.4038(18) yes
C2 . C17 . 1.4000(17) yes
C3 . C4 . 1.5161(17) yes
C3 . C14 . 1.3970(18) yes
C4 . O5 . 1.4238(15) yes
C4 . C6 . 1.5290(18) yes
C4 . H41 . 1.011 no
O5 . H51 . 0.821(14) no
C6 . C7 . 1.5160(17) yes
C6 . H61 . 0.992 no
C6 . H62 . 0.976 no
C7 . O8 . 1.4307(15) yes
C7 . C12 . 1.5109(18) yes
C7 . H71 . 0.953 no
O8 . C9 . 1.4299(16) yes
C9 . C10 . 1.511(2) yes
C9 . H91 . 1.015 no
C9 . H92 . 0.976 no
C10 . O11 . 1.4417(17) yes
C10 . C13 . 1.5136(19) yes
C10 . H101 . 1.000 no
O11 . C12 . 1.4352(16) yes
C12 . H122 . 1.032 no
C12 . H121 . 0.971 no
C13 . H131 . 0.979 no
C13 . H133 . 0.974 no
C13 . H132 . 0.955 no
C14 . C15 . 1.386(2) yes
C14 . H141 . 0.950 no
C15 . C16 . 1.378(2) yes
C15 . H151 . 0.943 no
C16 . C17 . 1.3857(19) yes
C16 . H161 . 0.977 no
C17 . H171 . 0.990 no
C18 . H182 . 0.973 no
C18 . H183 . 0.918 no
C18 . H181 . 0.994 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C18 . 103.78(7) yes
S1 . C2 . C3 . 118.34(9) yes
S1 . C2 . C17 . 122.13(10) yes
C3 . C2 . C17 . 119.52(12) yes
C2 . C3 . C4 . 121.73(11) yes
C2 . C3 . C14 . 118.63(12) yes
C4 . C3 . C14 . 119.59(12) yes
C3 . C4 . O5 . 110.90(10) yes
C3 . C4 . C6 . 109.92(10) yes
O5 . C4 . C6 . 108.19(10) yes
C3 . C4 . H41 . 108.3 no
O5 . C4 . H41 . 107.9 no
C6 . C4 . H41 . 111.6 no
C4 . O5 . H51 . 106.0(13) no
C4 . C6 . C7 . 113.44(10) yes
C4 . C6 . H61 . 107.5 no
C7 . C6 . H61 . 109.8 no
C4 . C6 . H62 . 107.2 no
C7 . C6 . H62 . 110.7 no
H61 . C6 . H62 . 108.0 no
C6 . C7 . O8 . 107.82(10) yes
C6 . C7 . C12 . 111.37(10) yes
O8 . C7 . C12 . 109.29(11) yes
C6 . C7 . H71 . 111.3 no
O8 . C7 . H71 . 108.5 no
C12 . C7 . H71 . 108.5 no
C7 . O8 . C9 . 110.34(10) yes
O8 . C9 . C10 . 111.53(11) yes
O8 . C9 . H91 . 106.5 no
C10 . C9 . H91 . 110.4 no
O8 . C9 . H92 . 107.9 no
C10 . C9 . H92 . 106.2 no
H91 . C9 . H92 . 114.4 no
C9 . C10 . O11 . 109.34(11) yes
C9 . C10 . C13 . 112.00(12) yes
O11 . C10 . C13 . 107.63(11) yes
C9 . C10 . H101 . 113.8 no
O11 . C10 . H101 . 102.1 no
C13 . C10 . H101 . 111.3 no
C10 . O11 . C12 . 111.39(10) yes
C7 . C12 . O11 . 111.60(10) yes
C7 . C12 . H122 . 109.1 no
O11 . C12 . H122 . 107.8 no
C7 . C12 . H121 . 112.0 no
O11 . C12 . H121 . 107.0 no
H122 . C12 . H121 . 109.3 no
C10 . C13 . H131 . 107.9 no
C10 . C13 . H133 . 112.3 no
H131 . C13 . H133 . 111.8 no
C10 . C13 . H132 . 110.4 no
H131 . C13 . H132 . 106.5 no
H133 . C13 . H132 . 107.8 no
C3 . C14 . C15 . 121.45(13) yes
C3 . C14 . H141 . 118.0 no
C15 . C14 . H141 . 120.5 no
C14 . C15 . C16 . 119.48(13) yes
C14 . C15 . H151 . 121.4 no
C16 . C15 . H151 . 119.1 no
C15 . C16 . C17 . 120.49(12) yes
C15 . C16 . H161 . 121.0 no
C17 . C16 . H161 . 118.4 no
C2 . C17 . C16 . 120.39(13) yes
C2 . C17 . H171 . 119.7 no
C16 . C17 . H171 . 119.8 no
S1 . C18 . H182 . 107.2 no
S1 . C18 . H183 . 106.9 no
H182 . C18 . H183 . 112.1 no
S1 . C18 . H181 . 111.7 no
H182 . C18 . H181 . 111.3 no
H183 . C18 . H181 . 107.6 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O5 4_645 153 1.01 2.35 3.283(2) yes
O5 . H51 . O11 4_645 177.0(18) 0.821(14) 1.892(14) 2.713(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.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_DM_phenyl_dioxane
_database_code_depnum_ccdc_archive 'CCDC 2091914'
loop_
_audit_author_name
_audit_author_address
'Antoine de Gombert'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The H atoms were all located in a difference map, but were 
repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98 Å) 
and 
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom), 
after which the positions were refined with riding constraints 
(Cooper et al, 2010). 
 
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 
43, 1100-1107. 

;


_cell_length_a                   23.8127(9)
_cell_length_b                   5.6108(2)
_cell_length_c                   24.8367(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.390(3)
_cell_angle_gamma                90
_cell_volume                     3318.3(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720
0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C19 H20 O3 S1 
# Dc =      1.31 Fooo =   1392.00 Mu =      2.07 M =    328.43
# Found Formula = C19 H20 O3 S1 
# Dc =      1.31 FOOO =   1392.00 Mu =      2.07 M =    328.43

_chemical_formula_sum            'C19 H20 O3 S1'
_chemical_formula_moiety         'C19 H20 O3 S1'
_chemical_compound_source        .
_chemical_formula_weight         328.43


_cell_measurement_reflns_used    6835
_cell_measurement_theta_min      1.73
_cell_measurement_theta_max      29.70
_cell_measurement_temperature    173

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.040
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_max          0.800

_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1392
_exptl_absorpt_coefficient_mu    0.207

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      173
_diffrn_reflns_number            39383
_reflns_number_total             9797
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 9797 
# Theoretical number of reflections is about 20367 


_diffrn_reflns_theta_min         1.710
_diffrn_reflns_theta_max         30.567
_diffrn_measured_fraction_theta_max 0.966

_diffrn_reflns_theta_full        25.982
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       32
_reflns_limit_h_min              -33
_reflns_limit_h_max              33
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              35

_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      4.46

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.51
_refine_diff_density_max         0.59


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     415
_refine_ls_number_reflns         9795
_oxford_refine_ls_R_factor_ref   0.0793
_refine_ls_R_factor_all          0.0793
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_all         0.1040
_refine_ls_goodness_of_fit_ref   1.0006
_refine_ls_shift/su_max          0.0007629
_refine_ls_shift/su_mean         0.0000480


# Computed with I/sigma = -10 
_oxford_reflns_number_all        9795
_oxford_refine_ls_R_factor_all   0.0793
_oxford_refine_ls_wR_factor_all  0.1040

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7012
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_gt          0.0937


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.83P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.537288(16) 0.90992(8) 0.364268(17) 0.0270 1.0000 Uani . . . . . .
C2 C 0.52451(6) 0.6962(3) 0.31329(6) 0.0215 1.0000 Uani . . . . . .
C3 C 0.56639(6) 0.5276(3) 0.29862(6) 0.0209 1.0000 Uani . . . . . .
C4 C 0.62376(6) 0.5417(3) 0.32243(6) 0.0219 1.0000 Uani . . . . . .
O5 O 0.63686(5) 0.7107(2) 0.35115(5) 0.0366 1.0000 Uani . . . . . .
C6 C 0.66626(6) 0.3478(3) 0.31099(6) 0.0226 1.0000 Uani . . . . . .
C7 C 0.72312(6) 0.3990(3) 0.33715(6) 0.0200 1.0000 Uani . . . . . .
O8 O 0.75503(4) 0.18258(19) 0.33344(5) 0.0247 1.0000 Uani . . . . . .
C9 C 0.80951(6) 0.2147(3) 0.35697(7) 0.0254 1.0000 Uani . . . . . .
C10 C 0.84158(6) 0.4146(3) 0.32933(6) 0.0202 1.0000 Uani . . . . . .
O11 O 0.80998(4) 0.63032(19) 0.33188(5) 0.0240 1.0000 Uani . . . . . .
C12 C 0.75470(6) 0.5979(3) 0.30910(6) 0.0224 1.0000 Uani . . . . . .
C13 C 0.89835(6) 0.4522(3) 0.35621(6) 0.0204 1.0000 Uani . . . . . .
C14 C 0.90942(6) 0.6449(3) 0.38989(6) 0.0240 1.0000 Uani . . . . . .
C15 C 0.96138(7) 0.6640(3) 0.41603(7) 0.0292 1.0000 Uani . . . . . .
C16 C 1.00202(6) 0.4896(3) 0.40904(7) 0.0302 1.0000 Uani . . . . . .
C17 C 0.99122(7) 0.2982(3) 0.37546(7) 0.0317 1.0000 Uani . . . . . .
C18 C 0.93970(6) 0.2800(3) 0.34888(7) 0.0279 1.0000 Uani . . . . . .
C19 C 0.55387(6) 0.3502(3) 0.26070(6) 0.0242 1.0000 Uani . . . . . .
C20 C 0.50188(7) 0.3404(3) 0.23501(6) 0.0273 1.0000 Uani . . . . . .
C21 C 0.46177(6) 0.5104(3) 0.24781(7) 0.0279 1.0000 Uani . . . . . .
C22 C 0.47220(6) 0.6831(3) 0.28631(7) 0.0265 1.0000 Uani . . . . . .
C23 C 0.47020(7) 1.0563(4) 0.37069(8) 0.0369 1.0000 Uani . . . . . .
S24 S 0.39931(2) 0.57447(9) 0.454357(19) 0.0374 1.0000 Uani . . . . . .
C25 C 0.42624(12) 0.6620(5) 0.51987(10) 0.0675 1.0000 Uani . . . . . .
C26 C 0.34970(7) 0.3514(3) 0.47033(7) 0.0290 1.0000 Uani . . . . . .
C27 C 0.32351(6) 0.2145(3) 0.42911(6) 0.0238 1.0000 Uani . . . . . .
C28 C 0.33516(6) 0.2605(3) 0.37147(6) 0.0228 1.0000 Uani . . . . . .
O29 O 0.35831(5) 0.4447(2) 0.35714(5) 0.0353 1.0000 Uani . . . . . .
C30 C 0.31878(6) 0.0725(3) 0.33011(6) 0.0226 1.0000 Uani . . . . . .
C31 C 0.34048(6) 0.1291(3) 0.27397(6) 0.0198 1.0000 Uani . . . . . .
O32 O 0.33575(4) -0.08756(19) 0.24331(4) 0.0229 1.0000 Uani . . . . . .
C33 C 0.35386(6) -0.0514(3) 0.18917(6) 0.0234 1.0000 Uani . . . . . .
C34 C 0.32029(6) 0.1452(3) 0.16150(6) 0.0202 1.0000 Uani . . . . . .
O35 O 0.32540(4) 0.36142(19) 0.19174(4) 0.0213 1.0000 Uani . . . . . .
C36 C 0.30739(6) 0.3261(3) 0.24649(6) 0.0207 1.0000 Uani . . . . . .
C37 C 0.34105(6) 0.1881(3) 0.10481(6) 0.0205 1.0000 Uani . . . . . .
C38 C 0.37496(6) 0.3819(3) 0.09228(6) 0.0246 1.0000 Uani . . . . . .
C39 C 0.39502(7) 0.4126(3) 0.03999(7) 0.0292 1.0000 Uani . . . . . .
C40 C 0.38203(7) 0.2480(3) 0.00029(7) 0.0301 1.0000 Uani . . . . . .
C41 C 0.34848(8) 0.0537(3) 0.01255(7) 0.0330 1.0000 Uani . . . . . .
C42 C 0.32763(7) 0.0241(3) 0.06431(7) 0.0285 1.0000 Uani . . . . . .
C43 C 0.28601(7) 0.0332(4) 0.44348(7) 0.0326 1.0000 Uani . . . . . .
C44 C 0.27263(9) -0.0119(4) 0.49690(8) 0.0451 1.0000 Uani . . . . . .
C45 C 0.29812(10) 0.1227(4) 0.53685(8) 0.0500 1.0000 Uani . . . . . .
C46 C 0.33619(9) 0.3005(4) 0.52392(7) 0.0425 1.0000 Uani . . . . . .
H61 H 0.6520 0.1947 0.3240 0.0285 1.0000 Uiso . . . . . .
H62 H 0.6711 0.3343 0.2715 0.0284 1.0000 Uiso . . . . . .
H71 H 0.7188 0.4388 0.3758 0.0244 1.0000 Uiso . . . . . .
H91 H 0.8300 0.0633 0.3517 0.0312 1.0000 Uiso . . . . . .
H92 H 0.8057 0.2533 0.3960 0.0308 1.0000 Uiso . . . . . .
H101 H 0.8475 0.3710 0.2906 0.0253 1.0000 Uiso . . . . . .
H121 H 0.7352 0.7500 0.3144 0.0272 1.0000 Uiso . . . . . .
H122 H 0.7582 0.5605 0.2701 0.0270 1.0000 Uiso . . . . . .
H141 H 0.8812 0.7656 0.3954 0.0303 1.0000 Uiso . . . . . .
H151 H 0.9688 0.7990 0.4389 0.0353 1.0000 Uiso . . . . . .
H161 H 1.0371 0.5004 0.4274 0.0365 1.0000 Uiso . . . . . .
H171 H 1.0190 0.1774 0.3697 0.0391 1.0000 Uiso . . . . . .
H181 H 0.9326 0.1473 0.3252 0.0342 1.0000 Uiso . . . . . .
H191 H 0.5816 0.2321 0.2516 0.0297 1.0000 Uiso . . . . . .
H201 H 0.4937 0.2186 0.2089 0.0344 1.0000 Uiso . . . . . .
H211 H 0.4258 0.5064 0.2296 0.0330 1.0000 Uiso . . . . . .
H221 H 0.4431 0.7941 0.2945 0.0324 1.0000 Uiso . . . . . .
H233 H 0.4737 1.1691 0.4002 0.0564 1.0000 Uiso . . . . . .
H232 H 0.4612 1.1418 0.3381 0.0559 1.0000 Uiso . . . . . .
H231 H 0.4410 0.9417 0.3787 0.0558 1.0000 Uiso . . . . . .
H253 H 0.4551 0.7808 0.5134 0.0990 1.0000 Uiso . . . . . .
H252 H 0.4417 0.5246 0.5389 0.0991 1.0000 Uiso . . . . . .
H251 H 0.3962 0.7345 0.5409 0.0988 1.0000 Uiso . . . . . .
H301 H 0.3338 -0.0805 0.3420 0.0274 1.0000 Uiso . . . . . .
H302 H 0.2777 0.0605 0.3292 0.0274 1.0000 Uiso . . . . . .
H311 H 0.3805 0.1746 0.2759 0.0228 1.0000 Uiso . . . . . .
H331 H 0.3941 -0.0111 0.1886 0.0282 1.0000 Uiso . . . . . .
H332 H 0.3475 -0.2034 0.1705 0.0281 1.0000 Uiso . . . . . .
H341 H 0.2799 0.0993 0.1609 0.0238 1.0000 Uiso . . . . . .
H361 H 0.3137 0.4783 0.2653 0.0247 1.0000 Uiso . . . . . .
H362 H 0.2674 0.2862 0.2464 0.0249 1.0000 Uiso . . . . . .
H381 H 0.3848 0.4956 0.1197 0.0305 1.0000 Uiso . . . . . .
H391 H 0.4176 0.5489 0.0312 0.0358 1.0000 Uiso . . . . . .
H401 H 0.3964 0.2667 -0.0351 0.0362 1.0000 Uiso . . . . . .
H411 H 0.3392 -0.0599 -0.0146 0.0406 1.0000 Uiso . . . . . .
H421 H 0.3040 -0.1105 0.0730 0.0349 1.0000 Uiso . . . . . .
H431 H 0.2692 -0.0616 0.4160 0.0396 1.0000 Uiso . . . . . .
H441 H 0.2466 -0.1348 0.5058 0.0548 1.0000 Uiso . . . . . .
H451 H 0.2893 0.0934 0.5736 0.0594 1.0000 Uiso . . . . . .
H461 H 0.3535 0.3885 0.5523 0.0512 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.5041(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . C2 . 1.7686(16) yes
S1 . C23 . 1.8043(17) yes
C2 . C3 . 1.424(2) yes
C2 . C22 . 1.412(2) yes
C3 . C4 . 1.487(2) yes
C3 . C19 . 1.401(2) yes
C4 . O5 . 1.2256(19) yes
C4 . C6 . 1.514(2) yes
C6 . C7 . 1.525(2) yes
C6 . H61 . 0.979 no
C6 . H62 . 0.992 no
C7 . O8 . 1.4359(18) yes
C7 . C12 . 1.518(2) yes
C7 . H71 . 0.991 no
O8 . C9 . 1.4308(17) yes
C9 . C10 . 1.523(2) yes
C9 . H91 . 0.989 no
C9 . H92 . 0.997 no
C10 . O11 . 1.4267(18) yes
C10 . C13 . 1.5184(19) yes
C10 . H101 . 1.004 no
O11 . C12 . 1.4407(17) yes
C12 . H121 . 0.981 no
C12 . H122 . 0.995 no
C13 . C14 . 1.391(2) yes
C13 . C18 . 1.392(2) yes
C14 . C15 . 1.398(2) yes
C14 . H141 . 0.964 no
C15 . C16 . 1.388(2) yes
C15 . H151 . 0.962 no
C16 . C17 . 1.383(3) yes
C16 . H161 . 0.951 no
C17 . C18 . 1.393(2) yes
C17 . H171 . 0.958 no
C18 . H181 . 0.963 no
C19 . C20 . 1.390(2) yes
C19 . H191 . 0.964 no
C20 . C21 . 1.388(2) yes
C20 . H201 . 0.961 no
C21 . C22 . 1.383(2) yes
C21 . H211 . 0.967 no
C22 . H221 . 0.955 no
C23 . H233 . 0.971 no
C23 . H232 . 0.964 no
C23 . H231 . 0.968 no
S24 . C25 . 1.812(2) yes
S24 . C26 . 1.7682(18) yes
C25 . H253 . 0.973 no
C25 . H252 . 0.975 no
C25 . H251 . 0.977 no
C26 . C27 . 1.421(2) yes
C26 . C46 . 1.401(2) yes
C27 . C28 . 1.483(2) yes
C27 . C43 . 1.402(2) yes
C28 . O29 . 1.225(2) yes
C28 . C30 . 1.521(2) yes
C30 . C31 . 1.524(2) yes
C30 . H301 . 0.975 no
C30 . H302 . 0.981 no
C31 . O32 . 1.4387(18) yes
C31 . C36 . 1.517(2) yes
C31 . H311 . 0.987 no
O32 . C33 . 1.4293(18) yes
C33 . C34 . 1.523(2) yes
C33 . H331 . 0.985 no
C33 . H332 . 0.982 no
C34 . O35 . 1.4315(18) yes
C34 . C37 . 1.515(2) yes
C34 . H341 . 0.997 no
O35 . C36 . 1.4425(18) yes
C36 . H361 . 0.984 no
C36 . H362 . 0.978 no
C37 . C38 . 1.391(2) yes
C37 . C42 . 1.399(2) yes
C38 . C39 . 1.397(2) yes
C38 . H381 . 0.961 no
C39 . C40 . 1.384(2) yes
C39 . H391 . 0.960 no
C40 . C41 . 1.387(3) yes
C40 . H401 . 0.952 no
C41 . C42 . 1.391(2) yes
C41 . H411 . 0.953 no
C42 . H421 . 0.967 no
C43 . C44 . 1.390(2) yes
C43 . H431 . 0.951 no
C44 . C45 . 1.384(3) yes
C44 . H441 . 0.954 no
C45 . C46 . 1.387(3) yes
C45 . H451 . 0.953 no
C46 . H461 . 0.953 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . S1 . C23 . 102.93(8) yes
S1 . C2 . C3 . 121.08(11) yes
S1 . C2 . C22 . 121.46(12) yes
C3 . C2 . C22 . 117.45(14) yes
C2 . C3 . C4 . 120.39(14) yes
C2 . C3 . C19 . 119.86(13) yes
C4 . C3 . C19 . 119.74(14) yes
C3 . C4 . O5 . 120.14(14) yes
C3 . C4 . C6 . 120.02(13) yes
O5 . C4 . C6 . 119.84(13) yes
C4 . C6 . C7 . 112.15(13) yes
C4 . C6 . H61 . 109.6 no
C7 . C6 . H61 . 109.5 no
C4 . C6 . H62 . 108.8 no
C7 . C6 . H62 . 109.1 no
H61 . C6 . H62 . 107.6 no
C6 . C7 . O8 . 106.37(12) yes
C6 . C7 . C12 . 112.60(12) yes
O8 . C7 . C12 . 109.16(12) yes
C6 . C7 . H71 . 111.0 no
O8 . C7 . H71 . 108.1 no
C12 . C7 . H71 . 109.5 no
C7 . O8 . C9 . 110.24(11) yes
O8 . C9 . C10 . 111.39(12) yes
O8 . C9 . H91 . 106.6 no
C10 . C9 . H91 . 108.9 no
O8 . C9 . H92 . 109.6 no
C10 . C9 . H92 . 109.1 no
H91 . C9 . H92 . 111.3 no
C9 . C10 . O11 . 109.77(12) yes
C9 . C10 . C13 . 110.59(12) yes
O11 . C10 . C13 . 109.33(12) yes
C9 . C10 . H101 . 109.1 no
O11 . C10 . H101 . 109.1 no
C13 . C10 . H101 . 108.9 no
C10 . O11 . C12 . 110.87(11) yes
C7 . C12 . O11 . 111.51(12) yes
C7 . C12 . H121 . 109.9 no
O11 . C12 . H121 . 105.7 no
C7 . C12 . H122 . 109.7 no
O11 . C12 . H122 . 109.1 no
H121 . C12 . H122 . 110.9 no
C10 . C13 . C14 . 122.47(14) yes
C10 . C13 . C18 . 118.32(14) yes
C14 . C13 . C18 . 119.13(13) yes
C13 . C14 . C15 . 120.17(15) yes
C13 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 119.7 no
C14 . C15 . C16 . 120.25(16) yes
C14 . C15 . H151 . 119.5 no
C16 . C15 . H151 . 120.2 no
C15 . C16 . C17 . 119.73(14) yes
C15 . C16 . H161 . 120.4 no
C17 . C16 . H161 . 119.9 no
C16 . C17 . C18 . 120.16(15) yes
C16 . C17 . H171 . 120.9 no
C18 . C17 . H171 . 119.0 no
C17 . C18 . C13 . 120.55(15) yes
C17 . C18 . H181 . 119.8 no
C13 . C18 . H181 . 119.7 no
C3 . C19 . C20 . 121.43(15) yes
C3 . C19 . H191 . 120.2 no
C20 . C19 . H191 . 118.4 no
C19 . C20 . C21 . 118.67(15) yes
C19 . C20 . H201 . 120.9 no
C21 . C20 . H201 . 120.5 no
C20 . C21 . C22 . 121.28(14) yes
C20 . C21 . H211 . 119.1 no
C22 . C21 . H211 . 119.6 no
C2 . C22 . C21 . 121.22(15) yes
C2 . C22 . H221 . 120.3 no
C21 . C22 . H221 . 118.5 no
S1 . C23 . H233 . 107.0 no
S1 . C23 . H232 . 110.1 no
H233 . C23 . H232 . 109.0 no
S1 . C23 . H231 . 110.7 no
H233 . C23 . H231 . 109.7 no
H232 . C23 . H231 . 110.3 no
C25 . S24 . C26 . 102.89(10) yes
S24 . C25 . H253 . 106.4 no
S24 . C25 . H252 . 110.5 no
H253 . C25 . H252 . 110.9 no
S24 . C25 . H251 . 109.6 no
H253 . C25 . H251 . 109.0 no
H252 . C25 . H251 . 110.3 no
S24 . C26 . C27 . 120.77(13) yes
S24 . C26 . C46 . 121.04(14) yes
C27 . C26 . C46 . 118.17(16) yes
C26 . C27 . C28 . 121.18(15) yes
C26 . C27 . C43 . 119.09(15) yes
C28 . C27 . C43 . 119.73(15) yes
C27 . C28 . O29 . 120.98(15) yes
C27 . C28 . C30 . 118.85(14) yes
O29 . C28 . C30 . 120.17(14) yes
C28 . C30 . C31 . 112.71(13) yes
C28 . C30 . H301 . 108.3 no
C31 . C30 . H301 . 109.5 no
C28 . C30 . H302 . 108.3 no
C31 . C30 . H302 . 109.8 no
H301 . C30 . H302 . 108.2 no
C30 . C31 . O32 . 106.39(12) yes
C30 . C31 . C36 . 112.67(12) yes
O32 . C31 . C36 . 109.82(11) yes
C30 . C31 . H311 . 110.1 no
O32 . C31 . H311 . 108.4 no
C36 . C31 . H311 . 109.4 no
C31 . O32 . C33 . 110.79(11) yes
O32 . C33 . C34 . 111.50(12) yes
O32 . C33 . H331 . 110.2 no
C34 . C33 . H331 . 109.6 no
O32 . C33 . H332 . 105.9 no
C34 . C33 . H332 . 109.7 no
H331 . C33 . H332 . 109.9 no
C33 . C34 . O35 . 109.54(12) yes
C33 . C34 . C37 . 111.14(12) yes
O35 . C34 . C37 . 109.02(12) yes
C33 . C34 . H341 . 108.9 no
O35 . C34 . H341 . 107.8 no
C37 . C34 . H341 . 110.4 no
C34 . O35 . C36 . 110.69(11) yes
C31 . C36 . O35 . 111.56(12) yes
C31 . C36 . H361 . 110.0 no
O35 . C36 . H361 . 106.3 no
C31 . C36 . H362 . 109.7 no
O35 . C36 . H362 . 109.0 no
H361 . C36 . H362 . 110.2 no
C34 . C37 . C38 . 121.72(14) yes
C34 . C37 . C42 . 119.32(14) yes
C38 . C37 . C42 . 118.91(14) yes
C37 . C38 . C39 . 120.46(15) yes
C37 . C38 . H381 . 120.0 no
C39 . C38 . H381 . 119.5 no
C38 . C39 . C40 . 120.24(16) yes
C38 . C39 . H391 . 120.2 no
C40 . C39 . H391 . 119.5 no
C39 . C40 . C41 . 119.63(15) yes
C39 . C40 . H401 . 120.4 no
C41 . C40 . H401 . 120.0 no
C40 . C41 . C42 . 120.42(16) yes
C40 . C41 . H411 . 120.1 no
C42 . C41 . H411 . 119.5 no
C37 . C42 . C41 . 120.32(16) yes
C37 . C42 . H421 . 118.9 no
C41 . C42 . H421 . 120.7 no
C27 . C43 . C44 . 121.72(17) yes
C27 . C43 . H431 . 119.3 no
C44 . C43 . H431 . 119.0 no
C43 . C44 . C45 . 118.88(18) yes
C43 . C44 . H441 . 120.4 no
C45 . C44 . H441 . 120.7 no
C44 . C45 . C46 . 120.70(18) yes
C44 . C45 . H451 . 119.7 no
C46 . C45 . H451 . 119.6 no
C26 . C46 . C45 . 121.42(17) yes
C26 . C46 . H461 . 119.8 no
C45 . C46 . H461 . 118.8 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C9 . H91 . O11 1_545 139 0.99 2.52 3.338(2) yes
C12 . H121 . O8 1_565 141 0.98 2.52 3.336(2) yes
C33 . H332 . O35 1_545 140 0.98 2.55 3.364(2) yes
C36 . H361 . O32 1_565 139 0.98 2.55 3.360(2) yes
C36 . H362 . O32 4_555 150 0.98 2.57 3.454(2) yes
C46 . H461 . O5 2_666 130 0.95 2.47 3.165(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 0 3 x .
2 0 0 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.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_DM3_067_v2
_database_code_depnum_ccdc_archive 'CCDC 2091915'
loop_
_audit_author_name
_audit_author_address
'Antoine de Gombert'
;University of Oxford
United Kingdom
;
_audit_update_record             
;
2021-06-24 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;

_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;
_refine_special_details          
; 
The H atoms were all located in a difference map, but were 
repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98 Å) 
and 
Uiso(H) (in the range 1.2-1.5 times Ueq of the parent atom), 
after which the positions were refined with riding constraints 
(Cooper et al, 2010). 
 
Cooper, R. I., Thompson, A. L. & Watkin, D. J. (2010). J. Appl. Cryst. 
43, 1100-1107. 

;
_cell_length_a                   11.6377(4)
_cell_length_b                   19.0350(7)
_cell_length_c                   18.0198(7)
_cell_angle_alpha                90
_cell_angle_beta                 107.936(4)
_cell_angle_gamma                90
_cell_volume                     3797.8(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C20 H27 N1 O5 
# Dc =      1.26 Fooo =   1552.00 Mu =      0.90 M =    361.44
# Found Formula = C20 H27 N1 O5 
# Dc =      1.26 FOOO =   1552.00 Mu =      0.90 M =    361.44

_chemical_formula_sum            'C20 H27 N1 O5'
_chemical_formula_moiety         'C20 H27 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         361.44


_cell_measurement_reflns_used    8500
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      30.35
_cell_measurement_temperature    170

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          0.800

_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.090

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      170
_diffrn_reflns_number            50277
_reflns_number_total             11263
_diffrn_reflns_av_R_equivalents  0.036
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 11263 
# Theoretical number of reflections is about 23290 


_diffrn_reflns_theta_min         1.839
_diffrn_reflns_theta_max         30.557
_diffrn_measured_fraction_theta_max 0.967

_diffrn_reflns_theta_full        27.196
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_oxford_diffrn_Wilson_B_factor   2.00
_oxford_diffrn_Wilson_scale      0.43

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.43
_refine_diff_density_max         0.58


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     0
_refine_ls_number_parameters     469
_refine_ls_number_reflns         11262
_oxford_refine_ls_R_factor_ref   0.0819
_refine_ls_R_factor_all          0.0819
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_all         0.1517
_refine_ls_goodness_of_fit_ref   0.9801
_refine_ls_shift/su_max          0.0006463
_refine_ls_shift/su_mean         0.0000632


# Computed with I/sigma = -10 
_oxford_reflns_number_all        11263
_oxford_refine_ls_R_factor_all   0.0819
_oxford_refine_ls_wR_factor_all  0.1518

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                7542
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_gt          0.1281


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 1.14P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.49953(10) 0.59314(5) 0.16138(6) 0.0301 1.0000 Uani . . . . . .
C2 C 0.53708(12) 0.52545(7) 0.19482(8) 0.0226 1.0000 Uani . . . . . .
C3 C 0.55466(12) 0.53022(7) 0.28109(8) 0.0218 1.0000 Uani . . . . . .
C4 C 0.65822(13) 0.50277(8) 0.33433(8) 0.0277 1.0000 Uani . . . . . .
C5 C 0.67259(14) 0.50543(9) 0.41374(9) 0.0349 1.0000 Uani . . . . . .
C6 C 0.58416(15) 0.53543(9) 0.44023(9) 0.0368 1.0000 Uani . . . . . .
C7 C 0.48105(15) 0.56297(9) 0.38765(9) 0.0362 1.0000 Uani . . . . . .
C8 C 0.46621(13) 0.56004(8) 0.30821(8) 0.0289 1.0000 Uani . . . . . .
C9 C 0.44187(12) 0.47052(7) 0.15520(7) 0.0222 1.0000 Uani . . . . . .
O10 O 0.42210(10) 0.47083(5) 0.07272(6) 0.0299 1.0000 Uani . . . . . .
C11 C 0.38501(16) 0.53878(8) 0.04072(9) 0.0360 1.0000 Uani . . . . . .
C12 C 0.47976(17) 0.59247(8) 0.07903(9) 0.0357 1.0000 Uani . . . . . .
C13 C 0.48156(12) 0.39699(7) 0.18262(8) 0.0240 1.0000 Uani . . . . . .
C14 C 0.37968(11) 0.34347(7) 0.16117(7) 0.0191 1.0000 Uani . . . . . .
O15 O 0.27631(8) 0.36033(5) 0.15350(6) 0.0270 1.0000 Uani . . . . . .
C16 C 0.41367(12) 0.26806(7) 0.14715(7) 0.0206 1.0000 Uani . . . . . .
C17 C 0.54074(11) 0.24871(7) 0.20151(7) 0.0194 1.0000 Uani . . . . . .
O18 O 0.61889(9) 0.22812(6) 0.17396(6) 0.0299 1.0000 Uani . . . . . .
N19 N 0.56496(9) 0.25650(6) 0.27991(6) 0.0206 1.0000 Uani . . . . . .
C20 C 0.47596(12) 0.26849(7) 0.32078(7) 0.0216 1.0000 Uani . . . . . .
C21 C 0.52993(14) 0.31179(9) 0.39353(8) 0.0307 1.0000 Uani . . . . . .
O22 O 0.63720(10) 0.27995(7) 0.44316(6) 0.0377 1.0000 Uani . . . . . .
C23 C 0.72561(14) 0.27695(9) 0.40317(9) 0.0361 1.0000 Uani . . . . . .
C24 C 0.68278(12) 0.23184(8) 0.33065(8) 0.0284 1.0000 Uani . . . . . .
C25 C 0.31741(13) 0.21472(7) 0.15296(9) 0.0289 1.0000 Uani . . . . . .
C26 C 0.41744(15) 0.26812(9) 0.06238(8) 0.0326 1.0000 Uani . . . . . .
O27 O 0.97091(10) 0.53814(5) 0.15520(6) 0.0305 1.0000 Uani . . . . . .
C28 C 1.01392(12) 0.60553(7) 0.18722(8) 0.0229 1.0000 Uani . . . . . .
C29 C 1.03985(12) 0.60236(7) 0.27426(7) 0.0216 1.0000 Uani . . . . . .
C30 C 1.14754(12) 0.62915(7) 0.32366(8) 0.0248 1.0000 Uani . . . . . .
C31 C 1.16926(13) 0.62929(8) 0.40409(8) 0.0294 1.0000 Uani . . . . . .
C32 C 1.08381(14) 0.60236(9) 0.43548(8) 0.0319 1.0000 Uani . . . . . .
C33 C 0.97706(15) 0.57462(10) 0.38659(9) 0.0375 1.0000 Uani . . . . . .
C34 C 0.95482(13) 0.57499(9) 0.30629(8) 0.0315 1.0000 Uani . . . . . .
C35 C 0.91894(12) 0.66169(7) 0.14968(8) 0.0233 1.0000 Uani . . . . . .
O36 O 0.89322(10) 0.66115(6) 0.06679(6) 0.0331 1.0000 Uani . . . . . .
C37 C 0.85199(17) 0.59348(9) 0.03601(9) 0.0386 1.0000 Uani . . . . . .
C38 C 0.94531(17) 0.53876(9) 0.07227(9) 0.0368 1.0000 Uani . . . . . .
C39 C 0.96334(12) 0.73467(7) 0.17658(8) 0.0253 1.0000 Uani . . . . . .
C40 C 0.86445(12) 0.79006(7) 0.15846(8) 0.0229 1.0000 Uani . . . . . .
O41 O 0.76019(9) 0.77490(6) 0.14979(7) 0.0343 1.0000 Uani . . . . . .
C42 C 0.90236(12) 0.86553(7) 0.14807(8) 0.0234 1.0000 Uani . . . . . .
C43 C 1.03237(12) 0.87988(7) 0.20112(8) 0.0237 1.0000 Uani . . . . . .
O44 O 1.11108(9) 0.89774(6) 0.17247(7) 0.0349 1.0000 Uani . . . . . .
N45 N 1.05870(10) 0.86959(6) 0.27931(7) 0.0245 1.0000 Uani . . . . . .
C46 C 0.97075(12) 0.86152(7) 0.32204(8) 0.0244 1.0000 Uani . . . . . .
C47 C 1.01985(14) 0.81487(9) 0.39297(9) 0.0328 1.0000 Uani . . . . . .
O48 O 1.13467(10) 0.83866(7) 0.44124(6) 0.0399 1.0000 Uani . . . . . .
C49 C 1.21790(14) 0.83499(9) 0.39713(10) 0.0376 1.0000 Uani . . . . . .
C50 C 1.18217(13) 0.88499(9) 0.32893(9) 0.0330 1.0000 Uani . . . . . .
C51 C 0.90161(15) 0.86804(9) 0.06249(9) 0.0369 1.0000 Uani . . . . . .
C52 C 0.81204(13) 0.92045(8) 0.15864(9) 0.0317 1.0000 Uani . . . . . .
H21 H 0.6156 0.5131 0.1852 0.0293 1.0000 Uiso . . . . . .
H41 H 0.7194 0.4807 0.3158 0.0356 1.0000 Uiso . . . . . .
H51 H 0.7442 0.4865 0.4514 0.0438 1.0000 Uiso . . . . . .
H61 H 0.5948 0.5367 0.4949 0.0460 1.0000 Uiso . . . . . .
H71 H 0.4183 0.5852 0.4068 0.0463 1.0000 Uiso . . . . . .
H81 H 0.3936 0.5798 0.2709 0.0369 1.0000 Uiso . . . . . .
H91 H 0.3623 0.4829 0.1668 0.0279 1.0000 Uiso . . . . . .
H112 H 0.3734 0.5365 -0.0161 0.0461 1.0000 Uiso . . . . . .
H111 H 0.3072 0.5496 0.0501 0.0460 1.0000 Uiso . . . . . .
H121 H 0.4485 0.6404 0.0593 0.0448 1.0000 Uiso . . . . . .
H122 H 0.5564 0.5804 0.0676 0.0460 1.0000 Uiso . . . . . .
H132 H 0.5147 0.3963 0.2403 0.0317 1.0000 Uiso . . . . . .
H131 H 0.5449 0.3808 0.1601 0.0317 1.0000 Uiso . . . . . .
H201 H 0.4067 0.2943 0.2870 0.0274 1.0000 Uiso . . . . . .
H202 H 0.4491 0.2234 0.3349 0.0280 1.0000 Uiso . . . . . .
H212 H 0.5468 0.3599 0.3782 0.0400 1.0000 Uiso . . . . . .
H211 H 0.4709 0.3136 0.4224 0.0391 1.0000 Uiso . . . . . .
H232 H 0.7999 0.2563 0.4400 0.0453 1.0000 Uiso . . . . . .
H231 H 0.7416 0.3256 0.3882 0.0453 1.0000 Uiso . . . . . .
H241 H 0.7400 0.2345 0.3006 0.0362 1.0000 Uiso . . . . . .
H242 H 0.6723 0.1833 0.3456 0.0368 1.0000 Uiso . . . . . .
H252 H 0.3425 0.1676 0.1414 0.0464 1.0000 Uiso . . . . . .
H251 H 0.3088 0.2148 0.2056 0.0461 1.0000 Uiso . . . . . .
H253 H 0.2398 0.2272 0.1149 0.0456 1.0000 Uiso . . . . . .
H262 H 0.4362 0.2201 0.0514 0.0522 1.0000 Uiso . . . . . .
H261 H 0.4762 0.3039 0.0574 0.0517 1.0000 Uiso . . . . . .
H263 H 0.3375 0.2803 0.0286 0.0500 1.0000 Uiso . . . . . .
H281 H 1.0914 0.6184 0.1741 0.0277 1.0000 Uiso . . . . . .
H301 H 1.2071 0.6482 0.3026 0.0310 1.0000 Uiso . . . . . .
H311 H 1.2450 0.6482 0.4376 0.0382 1.0000 Uiso . . . . . .
H321 H 1.0989 0.6027 0.4906 0.0408 1.0000 Uiso . . . . . .
H331 H 0.9182 0.5548 0.4092 0.0465 1.0000 Uiso . . . . . .
H341 H 0.8806 0.5560 0.2720 0.0394 1.0000 Uiso . . . . . .
H351 H 0.8400 0.6520 0.1623 0.0282 1.0000 Uiso . . . . . .
H372 H 0.8393 0.5958 -0.0208 0.0498 1.0000 Uiso . . . . . .
H371 H 0.7737 0.5826 0.0472 0.0500 1.0000 Uiso . . . . . .
H381 H 1.0224 0.5510 0.0602 0.0467 1.0000 Uiso . . . . . .
H382 H 0.9138 0.4908 0.0521 0.0475 1.0000 Uiso . . . . . .
H392 H 1.0282 0.7495 0.1533 0.0324 1.0000 Uiso . . . . . .
H391 H 0.9999 0.7344 0.2340 0.0334 1.0000 Uiso . . . . . .
H461 H 0.9544 0.9086 0.3398 0.0322 1.0000 Uiso . . . . . .
H462 H 0.8969 0.8408 0.2878 0.0311 1.0000 Uiso . . . . . .
H472 H 0.9641 0.8152 0.4248 0.0421 1.0000 Uiso . . . . . .
H471 H 1.0237 0.7669 0.3729 0.0419 1.0000 Uiso . . . . . .
H492 H 1.3000 0.8483 0.4338 0.0477 1.0000 Uiso . . . . . .
H491 H 1.2212 0.7857 0.3779 0.0470 1.0000 Uiso . . . . . .
H501 H 1.1849 0.9348 0.3477 0.0419 1.0000 Uiso . . . . . .
H502 H 1.2380 0.8800 0.2964 0.0416 1.0000 Uiso . . . . . .
H512 H 0.9299 0.9138 0.0526 0.0582 1.0000 Uiso . . . . . .
H511 H 0.9532 0.8306 0.0541 0.0572 1.0000 Uiso . . . . . .
H513 H 0.8190 0.8608 0.0304 0.0583 1.0000 Uiso . . . . . .
H522 H 0.8373 0.9674 0.1468 0.0508 1.0000 Uiso . . . . . .
H521 H 0.8060 0.9190 0.2109 0.0505 1.0000 Uiso . . . . . .
H523 H 0.7319 0.9088 0.1216 0.0510 1.0000 Uiso . . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.613(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.4324(16) yes
O1 . C12 . 1.4300(17) yes
C2 . C3 . 1.5071(18) yes
C2 . C9 . 1.5308(18) yes
C2 . H21 . 1.008 no
C3 . C4 . 1.3906(19) yes
C3 . C8 . 1.3894(19) yes
C4 . C5 . 1.389(2) yes
C4 . H41 . 0.970 no
C5 . C6 . 1.384(2) yes
C5 . H51 . 0.968 no
C6 . C7 . 1.383(2) yes
C6 . H61 . 0.955 no
C7 . C8 . 1.389(2) yes
C7 . H71 . 0.993 no
C8 . H81 . 0.978 no
C9 . O10 . 1.4324(16) yes
C9 . C13 . 1.5087(18) yes
C9 . H91 . 1.037 no
O10 . C11 . 1.4277(18) yes
C11 . C12 . 1.506(2) yes
C11 . H112 . 0.991 no
C11 . H111 . 0.993 no
C12 . H121 . 1.006 no
C12 . H122 . 1.001 no
C13 . C14 . 1.5200(18) yes
C13 . H132 . 0.991 no
C13 . H131 . 0.994 no
C14 . O15 . 1.2111(15) yes
C14 . C16 . 1.5305(18) yes
C16 . C17 . 1.5460(18) yes
C16 . C25 . 1.5391(19) yes
C16 . C26 . 1.5417(19) yes
C17 . O18 . 1.2269(15) yes
C17 . N19 . 1.3609(16) yes
N19 . C20 . 1.4618(16) yes
N19 . C24 . 1.4711(17) yes
C20 . C21 . 1.5117(19) yes
C20 . H201 . 0.979 no
C20 . H202 . 0.973 no
C21 . O22 . 1.4275(19) yes
C21 . H212 . 0.994 no
C21 . H211 . 0.981 no
O22 . C23 . 1.4275(19) yes
C23 . C24 . 1.514(2) yes
C23 . H232 . 0.995 no
C23 . H231 . 0.997 no
C24 . H241 . 0.980 no
C24 . H242 . 0.981 no
C25 . H252 . 0.985 no
C25 . H251 . 0.984 no
C25 . H253 . 0.980 no
C26 . H262 . 0.974 no
C26 . H261 . 0.989 no
C26 . H263 . 0.970 no
O27 . C28 . 1.4322(16) yes
O27 . C38 . 1.4311(17) yes
C28 . C29 . 1.5045(18) yes
C28 . C35 . 1.5367(19) yes
C28 . H281 . 1.030 no
C29 . C30 . 1.3914(18) yes
C29 . C34 . 1.3913(19) yes
C30 . C31 . 1.393(2) yes
C30 . H301 . 0.958 no
C31 . C32 . 1.385(2) yes
C31 . H311 . 0.971 no
C32 . C33 . 1.387(2) yes
C32 . H321 . 0.954 no
C33 . C34 . 1.389(2) yes
C33 . H331 . 0.974 no
C34 . H341 . 0.964 no
C35 . O36 . 1.4300(16) yes
C35 . C39 . 1.5093(18) yes
C35 . H351 . 1.028 no
O36 . C37 . 1.4259(19) yes
C37 . C38 . 1.501(2) yes
C37 . H372 . 0.989 no
C37 . H371 . 1.013 no
C38 . H381 . 1.014 no
C38 . H382 . 1.009 no
C39 . C40 . 1.5202(18) yes
C39 . H392 . 1.010 no
C39 . H391 . 0.991 no
C40 . O41 . 1.2096(16) yes
C40 . C42 . 1.5312(19) yes
C42 . C43 . 1.5450(19) yes
C42 . C51 . 1.540(2) yes
C42 . C52 . 1.5353(19) yes
C43 . O44 . 1.2297(16) yes
C43 . N45 . 1.3607(18) yes
N45 . C46 . 1.4663(17) yes
N45 . C50 . 1.4693(17) yes
C46 . C47 . 1.516(2) yes
C46 . H461 . 0.989 no
C46 . H462 . 0.974 no
C47 . O48 . 1.4253(19) yes
C47 . H472 . 0.990 no
C47 . H471 . 0.989 no
O48 . C49 . 1.431(2) yes
C49 . C50 . 1.508(2) yes
C49 . H492 . 1.013 no
C49 . H491 . 1.006 no
C50 . H501 . 1.003 no
C50 . H502 . 1.005 no
C51 . H512 . 0.966 no
C51 . H511 . 0.973 no
C51 . H513 . 0.967 no
C52 . H522 . 0.985 no
C52 . H521 . 0.967 no
C52 . H523 . 0.991 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . O1 . C12 . 111.05(10) yes
O1 . C2 . C3 . 107.86(10) yes
O1 . C2 . C9 . 109.57(11) yes
C3 . C2 . C9 . 111.77(11) yes
O1 . C2 . H21 . 108.2 no
C3 . C2 . H21 . 110.4 no
C9 . C2 . H21 . 108.9 no
C2 . C3 . C4 . 120.17(12) yes
C2 . C3 . C8 . 120.50(12) yes
C4 . C3 . C8 . 119.31(13) yes
C3 . C4 . C5 . 120.04(14) yes
C3 . C4 . H41 . 119.8 no
C5 . C4 . H41 . 120.1 no
C4 . C5 . C6 . 120.25(14) yes
C4 . C5 . H51 . 120.9 no
C6 . C5 . H51 . 118.9 no
C5 . C6 . C7 . 120.04(14) yes
C5 . C6 . H61 . 119.5 no
C7 . C6 . H61 . 120.5 no
C6 . C7 . C8 . 119.81(14) yes
C6 . C7 . H71 . 120.0 no
C8 . C7 . H71 . 120.2 no
C3 . C8 . C7 . 120.55(13) yes
C3 . C8 . H81 . 119.5 no
C7 . C8 . H81 . 120.0 no
C2 . C9 . O10 . 110.06(10) yes
C2 . C9 . C13 . 112.11(11) yes
O10 . C9 . C13 . 106.19(10) yes
C2 . C9 . H91 . 108.3 no
O10 . C9 . H91 . 109.9 no
C13 . C9 . H91 . 110.3 no
C9 . O10 . C11 . 110.78(10) yes
O10 . C11 . C12 . 110.00(13) yes
O10 . C11 . H112 . 107.7 no
C12 . C11 . H112 . 110.5 no
O10 . C11 . H111 . 107.3 no
C12 . C11 . H111 . 111.1 no
H112 . C11 . H111 . 110.1 no
C11 . C12 . O1 . 110.05(12) yes
C11 . C12 . H121 . 108.6 no
O1 . C12 . H121 . 106.5 no
C11 . C12 . H122 . 108.8 no
O1 . C12 . H122 . 110.2 no
H121 . C12 . H122 . 112.5 no
C9 . C13 . C14 . 113.73(11) yes
C9 . C13 . H132 . 109.7 no
C14 . C13 . H132 . 106.2 no
C9 . C13 . H131 . 110.1 no
C14 . C13 . H131 . 107.9 no
H132 . C13 . H131 . 109.0 no
C13 . C14 . O15 . 121.40(12) yes
C13 . C14 . C16 . 116.71(11) yes
O15 . C14 . C16 . 121.85(12) yes
C14 . C16 . C17 . 111.36(10) yes
C14 . C16 . C25 . 112.15(11) yes
C17 . C16 . C25 . 111.96(11) yes
C14 . C16 . C26 . 104.51(11) yes
C17 . C16 . C26 . 108.33(11) yes
C25 . C16 . C26 . 108.14(11) yes
C16 . C17 . O18 . 120.22(12) yes
C16 . C17 . N19 . 118.93(11) yes
O18 . C17 . N19 . 120.84(12) yes
C17 . N19 . C20 . 125.99(10) yes
C17 . N19 . C24 . 117.76(11) yes
C20 . N19 . C24 . 113.96(10) yes
N19 . C20 . C21 . 110.63(11) yes
N19 . C20 . H201 . 109.9 no
C21 . C20 . H201 . 108.0 no
N19 . C20 . H202 . 109.2 no
C21 . C20 . H202 . 109.6 no
H201 . C20 . H202 . 109.6 no
C20 . C21 . O22 . 111.19(12) yes
C20 . C21 . H212 . 109.0 no
O22 . C21 . H212 . 110.8 no
C20 . C21 . H211 . 107.9 no
O22 . C21 . H211 . 107.6 no
H212 . C21 . H211 . 110.3 no
C21 . O22 . C23 . 109.14(11) yes
O22 . C23 . C24 . 111.19(12) yes
O22 . C23 . H232 . 107.0 no
C24 . C23 . H232 . 109.8 no
O22 . C23 . H231 . 108.8 no
C24 . C23 . H231 . 109.4 no
H232 . C23 . H231 . 110.6 no
C23 . C24 . N19 . 110.58(12) yes
C23 . C24 . H241 . 110.4 no
N19 . C24 . H241 . 107.5 no
C23 . C24 . H242 . 109.5 no
N19 . C24 . H242 . 107.5 no
H241 . C24 . H242 . 111.4 no
C16 . C25 . H252 . 108.5 no
C16 . C25 . H251 . 110.9 no
H252 . C25 . H251 . 109.3 no
C16 . C25 . H253 . 109.0 no
H252 . C25 . H253 . 110.0 no
H251 . C25 . H253 . 109.2 no
C16 . C26 . H262 . 106.1 no
C16 . C26 . H261 . 108.8 no
H262 . C26 . H261 . 115.0 no
C16 . C26 . H263 . 107.9 no
H262 . C26 . H263 . 109.2 no
H261 . C26 . H263 . 109.5 no
C28 . O27 . C38 . 110.35(11) yes
O27 . C28 . C29 . 108.48(11) yes
O27 . C28 . C35 . 109.32(11) yes
C29 . C28 . C35 . 111.90(11) yes
O27 . C28 . H281 . 110.0 no
C29 . C28 . H281 . 109.9 no
C35 . C28 . H281 . 107.2 no
C28 . C29 . C30 . 120.27(12) yes
C28 . C29 . C34 . 120.51(12) yes
C30 . C29 . C34 . 119.18(12) yes
C29 . C30 . C31 . 120.37(13) yes
C29 . C30 . H301 . 120.3 no
C31 . C30 . H301 . 119.4 no
C30 . C31 . C32 . 120.09(13) yes
C30 . C31 . H311 . 119.2 no
C32 . C31 . H311 . 120.7 no
C31 . C32 . C33 . 119.79(13) yes
C31 . C32 . H321 . 119.8 no
C33 . C32 . H321 . 120.4 no
C32 . C33 . C34 . 120.18(14) yes
C32 . C33 . H331 . 119.3 no
C34 . C33 . H331 . 120.5 no
C29 . C34 . C33 . 120.38(13) yes
C29 . C34 . H341 . 119.0 no
C33 . C34 . H341 . 120.6 no
C28 . C35 . O36 . 110.22(11) yes
C28 . C35 . C39 . 111.73(11) yes
O36 . C35 . C39 . 106.43(11) yes
C28 . C35 . H351 . 110.4 no
O36 . C35 . H351 . 108.4 no
C39 . C35 . H351 . 109.6 no
C35 . O36 . C37 . 110.48(11) yes
O36 . C37 . C38 . 110.23(13) yes
O36 . C37 . H372 . 106.7 no
C38 . C37 . H372 . 109.8 no
O36 . C37 . H371 . 108.8 no
C38 . C37 . H371 . 110.2 no
H372 . C37 . H371 . 111.0 no
C37 . C38 . O27 . 110.50(13) yes
C37 . C38 . H381 . 108.5 no
O27 . C38 . H381 . 108.2 no
C37 . C38 . H382 . 109.7 no
O27 . C38 . H382 . 107.7 no
H381 . C38 . H382 . 112.2 no
C35 . C39 . C40 . 114.06(11) yes
C35 . C39 . H392 . 110.5 no
C40 . C39 . H392 . 109.2 no
C35 . C39 . H391 . 109.0 no
C40 . C39 . H391 . 106.3 no
H392 . C39 . H391 . 107.5 no
C39 . C40 . O41 . 121.68(13) yes
C39 . C40 . C42 . 116.70(11) yes
O41 . C40 . C42 . 121.56(12) yes
C40 . C42 . C43 . 110.76(11) yes
C40 . C42 . C51 . 103.80(12) yes
C43 . C42 . C51 . 108.46(11) yes
C40 . C42 . C52 . 112.92(11) yes
C43 . C42 . C52 . 112.35(12) yes
C51 . C42 . C52 . 108.07(12) yes
C42 . C43 . O44 . 120.21(13) yes
C42 . C43 . N45 . 118.73(11) yes
O44 . C43 . N45 . 121.01(13) yes
C43 . N45 . C46 . 126.01(11) yes
C43 . N45 . C50 . 117.88(12) yes
C46 . N45 . C50 . 114.29(11) yes
N45 . C46 . C47 . 111.18(11) yes
N45 . C46 . H461 . 108.1 no
C47 . C46 . H461 . 108.5 no
N45 . C46 . H462 . 109.5 no
C47 . C46 . H462 . 109.0 no
H461 . C46 . H462 . 110.6 no
C46 . C47 . O48 . 111.56(13) yes
C46 . C47 . H472 . 110.0 no
O48 . C47 . H472 . 107.6 no
C46 . C47 . H471 . 106.3 no
O48 . C47 . H471 . 112.2 no
H472 . C47 . H471 . 109.3 no
C47 . O48 . C49 . 108.25(11) yes
O48 . C49 . C50 . 110.97(12) yes
O48 . C49 . H492 . 106.8 no
C50 . C49 . H492 . 110.0 no
O48 . C49 . H491 . 109.9 no
C50 . C49 . H491 . 109.8 no
H492 . C49 . H491 . 109.3 no
C49 . C50 . N45 . 110.03(13) yes
C49 . C50 . H501 . 110.5 no
N45 . C50 . H501 . 108.5 no
C49 . C50 . H502 . 110.5 no
N45 . C50 . H502 . 108.2 no
H501 . C50 . H502 . 109.1 no
C42 . C51 . H512 . 108.3 no
C42 . C51 . H511 . 108.6 no
H512 . C51 . H511 . 111.7 no
C42 . C51 . H513 . 107.0 no
H512 . C51 . H513 . 110.6 no
H511 . C51 . H513 . 110.4 no
C42 . C52 . H522 . 109.3 no
C42 . C52 . H521 . 111.1 no
H522 . C52 . H521 . 110.6 no
C42 . C52 . H523 . 107.7 no
H522 . C52 . H523 . 109.8 no
H521 . C52 . H523 . 108.3 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 . H41 . O44 4_745 153 0.97 2.49 3.380(2) yes
C20 . H201 . C14 . 129 0.98 2.38 3.095(2) yes
C20 . H202 . O1 4_645 141 0.97 2.55 3.357(2) yes
C25 . H251 . C20 . 120 0.98 2.58 3.187(2) yes
C30 . H301 . O18 4_755 145 0.96 2.46 3.297(2) yes
C31 . H311 . O22 2_766 150 0.97 2.56 3.437(2) yes
C37 . H372 . O15 2_665 150 0.99 2.50 3.395(2) yes
C46 . H462 . C40 . 128 0.97 2.44 3.134(2) yes
C49 . H491 . O18 4_755 129 1.01 2.57 3.299(2) yes
C52 . H521 . C46 . 121 0.97 2.55 3.161(2) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
