# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1817419'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;
#============================================================================== 
_audit_creation_date             2016-07-28
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 6603
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   8.5004(2)
_cell_length_b                   12.8701(2)
_cell_length_c                   16.4218(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1796.56(6)

_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

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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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            4

# Given Formula = C16 H26 N2 O7 
# Dc =      1.32 Fooo =    768.00 Mu =      8.75 M =    358.39
# Found Formula = C16 H26.00 N2 O7 
# Dc =      1.32 FOOO =    768.00 Mu =      8.75 M =    358.39

_chemical_formula_sum            'C16 H26 N2 O7'
_chemical_formula_moiety         'C16 H26 N2 O7'
_chemical_compound_source        .
_chemical_formula_weight         358.39

_cell_measurement_reflns_used    12446
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.14
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             768.000
_exptl_absorpt_coefficient_mu    0.875

# Sheldrick geometric approximatio 0.85 0.88 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_T_max  0.88
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_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       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_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      150
_diffrn_reflns_number            22249
_reflns_number_total             3754
_diffrn_reflns_av_R_equivalents  0.038
_diffrn_reflns_av_sigmaI/netI    0.0414
# Number of reflections without Friedels Law is 3754 
# Number of reflections with Friedels Law is 2157 
# Theoretical number of reflections is about 1880 

_diffrn_reflns_theta_min         4.365
_diffrn_reflns_theta_max         76.168
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        76.168
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.38
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.27


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     30
_refine_ls_number_parameters     236
_oxford_refine_ls_R_factor_ref   0.0362
_refine_ls_wR_factor_ref         0.0958
_refine_ls_goodness_of_fit_ref   1.0118
_refine_ls_shift/su_max          0.0004836
_refine_ls_shift/su_mean         0.0000415


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3739
_refine_ls_R_factor_all          0.0362
_refine_ls_wR_factor_all         0.0958

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3660
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_gt          0.0950

_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_abs_structure_details 'Flack (1983), 1597 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    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 0.19P] 
 ,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
N1 N 0.30977(12) 0.56267(8) 0.54226(6) 0.0195 1.0000 Uani . . . . . .
C2 C 0.35268(16) 0.52806(10) 0.45971(7) 0.0222 1.0000 Uani . . . . . .
O3 O 0.20431(13) 0.51227(9) 0.42081(6) 0.0314 1.0000 Uani . . . . . .
C4 C 0.08081(16) 0.55950(11) 0.46689(8) 0.0271 1.0000 Uani . . . . . .
C5 C 0.13940(14) 0.55985(10) 0.55511(7) 0.0213 1.0000 Uani . . . . . .
C6 C 0.10782(14) 0.66134(10) 0.60522(7) 0.0215 1.0000 Uani . . . . . .
C7 C 0.26471(14) 0.68169(10) 0.64628(7) 0.0214 1.0000 Uani . . . . . .
O7 O 0.50967(12) 0.67937(8) 0.56526(6) 0.0272 1.0000 Uani . . . . . .
C8 C 0.38122(14) 0.64418(9) 0.58116(7) 0.0199 1.0000 Uani . . . . . .
C9 C 0.28842(16) 0.79507(10) 0.66891(8) 0.0240 1.0000 Uani . U . . . .
O10 O 0.21435(16) 0.86439(9) 0.63733(8) 0.0420 1.0000 Uani . . . . . .
N11 N 0.39223(16) 0.81479(10) 0.72943(7) 0.0318 1.0000 Uani D U . . . .
C12 C 0.4434(2) 0.91920(14) 0.74913(11) 0.0440 1.0000 Uani . U . . . .
O13 O 0.50422(13) 0.73673(9) 0.74693(7) 0.0300 0.895(3) Uani D U P 1 1 .
C14 C 0.4760(4) 0.6965(3) 0.82729(18) 0.0502 0.895(3) Uani D U P 1 1 .
O15 O -0.01285(11) 0.65304(8) 0.66278(6) 0.0292 1.0000 Uani . . . . . .
C16 C -0.16514(16) 0.66261(12) 0.62676(10) 0.0338 1.0000 Uani . . . . . .
C17 C 0.08367(16) 0.46582(10) 0.60456(8) 0.0253 1.0000 Uani . . . . . .
O18 O -0.03021(14) 0.41526(9) 0.58806(8) 0.0417 1.0000 Uani . . . . . .
O19 O 0.17433(12) 0.45127(8) 0.66991(6) 0.0275 1.0000 Uani . . . . . .
C20 C 0.1223(2) 0.37182(12) 0.72603(10) 0.0369 1.0000 Uani . . . . . .
C21 C 0.44842(17) 0.42724(10) 0.45614(8) 0.0255 1.0000 Uani . . . . . .
C22 C 0.60425(17) 0.44441(12) 0.50062(9) 0.0317 1.0000 Uani . . . . . .
C23 C 0.4834(2) 0.40441(12) 0.36593(9) 0.0367 1.0000 Uani . . . . . .
C24 C 0.3577(2) 0.33709(10) 0.49436(9) 0.0334 1.0000 Uani . . . . . .
O113 O 0.3633(13) 0.7466(8) 0.7960(6) 0.0394(15) 0.105(3) Uiso D U P 1 2 .
C114 C 0.505(3) 0.692(3) 0.8157(19) 0.039(2) 0.105(3) Uiso D U P 1 2 .
H21 H 0.4132 0.5853 0.4331 0.0249 1.0000 Uiso R . . . . .
H42 H 0.0620 0.6306 0.4465 0.0310 1.0000 Uiso R . . . . .
H41 H -0.0132 0.5160 0.4599 0.0341 1.0000 Uiso R . . . . .
H61 H 0.0830 0.7174 0.5684 0.0241 1.0000 Uiso R . . . . .
H71 H 0.2759 0.6379 0.6944 0.0253 1.0000 Uiso R . . . . .
H122 H 0.4858 0.9208 0.8036 0.0661 1.0000 Uiso R . . . . .
H121 H 0.3524 0.9613 0.7520 0.0654 1.0000 Uiso R . . . . .
H123 H 0.5223 0.9509 0.7116 0.0664 1.0000 Uiso R . . . . .
H143 H 0.5645 0.6546 0.8446 0.0740 0.895(3) Uiso R . P 1 1 .
H142 H 0.4625 0.7522 0.8660 0.0743 0.895(3) Uiso R . P 1 1 .
H141 H 0.3834 0.6523 0.8281 0.0739 0.895(3) Uiso R . P 1 1 .
H163 H -0.2409 0.6561 0.6697 0.0505 1.0000 Uiso R . . . . .
H162 H -0.1772 0.7278 0.5994 0.0499 1.0000 Uiso R . . . . .
H161 H -0.1839 0.6070 0.5876 0.0499 1.0000 Uiso R . . . . .
H201 H 0.1843 0.3777 0.7759 0.0554 1.0000 Uiso R . . . . .
H203 H 0.0131 0.3827 0.7359 0.0561 1.0000 Uiso R . . . . .
H202 H 0.1362 0.3062 0.7003 0.0551 1.0000 Uiso R . . . . .
H221 H 0.6725 0.3865 0.4945 0.0469 1.0000 Uiso R . . . . .
H223 H 0.5905 0.4568 0.5588 0.0462 1.0000 Uiso R . . . . .
H222 H 0.6560 0.5014 0.4769 0.0464 1.0000 Uiso R . . . . .
H231 H 0.5458 0.3419 0.3612 0.0550 1.0000 Uiso R . . . . .
H232 H 0.5437 0.4609 0.3401 0.0526 1.0000 Uiso R . . . . .
H233 H 0.3857 0.3953 0.3357 0.0542 1.0000 Uiso R . . . . .
H242 H 0.4137 0.2730 0.4871 0.0483 1.0000 Uiso R . . . . .
H241 H 0.3450 0.3489 0.5523 0.0477 1.0000 Uiso R . . . . .
H243 H 0.2578 0.3302 0.4700 0.0474 1.0000 Uiso R . . . . .
H1142 H 0.4817 0.6365 0.8523 0.0589 0.105(3) Uiso R . P 1 2 .
H1141 H 0.5783 0.7393 0.8410 0.0590 0.105(3) Uiso R . P 1 2 .
H1143 H 0.5504 0.6646 0.7667 0.0590 0.105(3) Uiso R . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.9(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
N1 . C2 . 1.4729(15) yes
N1 . C5 . 1.4640(16) yes
N1 . C8 . 1.3702(16) yes
C2 . O3 . 1.4283(16) yes
C2 . C21 . 1.5327(17) yes
C2 . H21 . 0.998 no
O3 . C4 . 1.4297(17) yes
C4 . C5 . 1.5320(16) yes
C4 . H42 . 0.987 no
C4 . H41 . 0.982 no
C5 . C6 . 1.5670(16) yes
C5 . C17 . 1.5325(18) yes
C6 . C7 . 1.5171(16) yes
C6 . O15 . 1.3989(15) yes
C6 . H61 . 0.965 no
C7 . C8 . 1.5355(17) yes
C7 . C9 . 1.5191(17) yes
C7 . H71 . 0.975 no
O7 . C8 . 1.2105(17) yes
C9 . O10 . 1.2089(18) yes
C9 . N11 . 1.3531(18) yes
N11 . C12 . 1.4491(19) yes
N11 . O13 . 1.4135(17) yes
N11 . C12 . 1.4491(19) yes
N11 . O113 . 1.423(7) yes
C12 . H122 . 0.964 no
C12 . H121 . 0.946 no
C12 . H123 . 0.997 no
O13 . C14 . 1.438(2) yes
C14 . H143 . 0.968 no
C14 . H142 . 0.966 no
C14 . H141 . 0.971 no
O15 . C16 . 1.4286(17) yes
C16 . H163 . 0.959 no
C16 . H162 . 0.957 no
C16 . H161 . 0.975 no
C17 . O18 . 1.1975(18) yes
C17 . O19 . 1.3344(17) yes
O19 . C20 . 1.4457(17) yes
C20 . H201 . 0.977 no
C20 . H203 . 0.953 no
C20 . H202 . 0.952 no
C21 . C22 . 1.529(2) yes
C21 . C23 . 1.5393(18) yes
C21 . C24 . 1.528(2) yes
C22 . H221 . 0.950 no
C22 . H223 . 0.976 no
C22 . H222 . 0.940 no
C23 . H231 . 0.967 no
C23 . H232 . 0.985 no
C23 . H233 . 0.974 no
C24 . H242 . 0.960 no
C24 . H241 . 0.970 no
C24 . H243 . 0.943 no
O113 . C114 . 1.430(10) yes
C114 . H1142 . 0.959 no
C114 . H1141 . 0.962 no
C114 . H1143 . 0.960 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 . N1 . C5 . 111.73(10) yes
C2 . N1 . C8 . 123.42(11) yes
C5 . N1 . C8 . 112.97(10) yes
N1 . C2 . O3 . 103.65(10) yes
N1 . C2 . C21 . 115.00(10) yes
O3 . C2 . C21 . 109.35(10) yes
N1 . C2 . H21 . 107.9 no
O3 . C2 . H21 . 111.4 no
C21 . C2 . H21 . 109.5 no
C2 . O3 . C4 . 110.56(9) yes
O3 . C4 . C5 . 105.25(10) yes
O3 . C4 . H42 . 109.5 no
C5 . C4 . H42 . 111.7 no
O3 . C4 . H41 . 107.0 no
C5 . C4 . H41 . 112.1 no
H42 . C4 . H41 . 110.9 no
C4 . C5 . N1 . 100.68(10) yes
C4 . C5 . C6 . 116.33(10) yes
N1 . C5 . C6 . 102.97(10) yes
C4 . C5 . C17 . 113.47(11) yes
N1 . C5 . C17 . 113.69(11) yes
C6 . C5 . C17 . 109.09(10) yes
C5 . C6 . C7 . 103.11(10) yes
C5 . C6 . O15 . 114.63(10) yes
C7 . C6 . O15 . 110.95(10) yes
C5 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 110.0 no
O15 . C6 . H61 . 108.7 no
C6 . C7 . C8 . 101.72(9) yes
C6 . C7 . C9 . 113.03(11) yes
C8 . C7 . C9 . 112.75(10) yes
C6 . C7 . H71 . 110.3 no
C8 . C7 . H71 . 108.7 no
C9 . C7 . H71 . 110.1 no
C7 . C8 . N1 . 106.23(10) yes
C7 . C8 . O7 . 127.90(11) yes
N1 . C8 . O7 . 125.86(12) yes
C7 . C9 . O10 . 122.33(12) yes
C7 . C9 . N11 . 116.51(12) yes
O10 . C9 . N11 . 121.09(13) yes
C9 . N11 . C12 . 122.25(13) yes
C9 . N11 . O13 . 117.08(11) yes
C12 . N11 . O13 . 114.30(13) yes
C9 . N11 . C12 . 122.25(13) yes
C9 . N11 . O113 . 109.6(5) yes
C12 . N11 . O113 . 116.9(5) yes
N11 . C12 . H122 . 109.8 no
N11 . C12 . H121 . 107.2 no
H122 . C12 . H121 . 104.3 no
N11 . C12 . H123 . 116.3 no
H122 . C12 . H123 . 108.2 no
H121 . C12 . H123 . 110.3 no
N11 . O13 . C14 . 109.29(8) yes
O13 . C14 . H143 . 109.9 no
O13 . C14 . H142 . 110.9 no
H143 . C14 . H142 . 108.2 no
O13 . C14 . H141 . 111.0 no
H143 . C14 . H141 . 107.5 no
H142 . C14 . H141 . 109.2 no
C6 . O15 . C16 . 112.22(11) yes
O15 . C16 . H163 . 107.2 no
O15 . C16 . H162 . 111.6 no
H163 . C16 . H162 . 110.5 no
O15 . C16 . H161 . 111.0 no
H163 . C16 . H161 . 108.1 no
H162 . C16 . H161 . 108.4 no
C5 . C17 . O18 . 123.99(13) yes
C5 . C17 . O19 . 111.01(11) yes
O18 . C17 . O19 . 124.93(13) yes
C17 . O19 . C20 . 115.80(12) yes
O19 . C20 . H201 . 108.4 no
O19 . C20 . H203 . 107.6 no
H201 . C20 . H203 . 111.8 no
O19 . C20 . H202 . 107.9 no
H201 . C20 . H202 . 111.9 no
H203 . C20 . H202 . 109.1 no
C2 . C21 . C22 . 108.63(11) yes
C2 . C21 . C23 . 107.50(11) yes
C22 . C21 . C23 . 108.68(12) yes
C2 . C21 . C24 . 111.06(12) yes
C22 . C21 . C24 . 110.53(12) yes
C23 . C21 . C24 . 110.35(12) yes
C21 . C22 . H221 . 111.4 no
C21 . C22 . H223 . 112.8 no
H221 . C22 . H223 . 107.7 no
C21 . C22 . H222 . 108.6 no
H221 . C22 . H222 . 106.4 no
H223 . C22 . H222 . 109.6 no
C21 . C23 . H231 . 110.0 no
C21 . C23 . H232 . 112.0 no
H231 . C23 . H232 . 107.1 no
C21 . C23 . H233 . 110.4 no
H231 . C23 . H233 . 109.1 no
H232 . C23 . H233 . 108.2 no
C21 . C24 . H242 . 110.6 no
C21 . C24 . H241 . 109.9 no
H242 . C24 . H241 . 108.2 no
C21 . C24 . H243 . 110.6 no
H242 . C24 . H243 . 108.2 no
H241 . C24 . H243 . 109.3 no
N11 . O113 . C114 . 109.22(10) yes
O113 . C114 . H1142 . 109.4 no
O113 . C114 . H1141 . 109.6 no
H1142 . C114 . H1141 . 109.5 no
O113 . C114 . H1143 . 109.2 no
H1142 . C114 . H1143 . 109.3 no
H1141 . C114 . H1143 . 109.7 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 . H42 . O7 3_466 164.66(4) 0.987 2.493 3.455(5) yes
C22 . H222 . O10 3_566 155.23(4) 0.940 2.597 3.473(5) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 28/07/16 at 15:58:22
#
#LIST     12                                                                    
BLOCK SCALE X'S, FIRST(U'S) UNTIL C(24) 
CONT O(113,U[ISO]) UNTIL C(114) 
CONT ENANTIO 
EQUIV PART(1001,OCC) PART(1002,OCC) 
WEIGHT -1 PART(1002,OCC) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   4,X'S) H   (  42,X'S) H   (  41,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) H   ( 123,X'S) 
RIDE C   (  14,X'S) H   ( 143,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE C   (  16,X'S) H   ( 163,X'S) H   ( 162,X'S) H   ( 161,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 203,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 223,X'S) H   ( 222,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) H   ( 233,X'S) 
RIDE C   (  24,X'S) H   ( 242,X'S) H   ( 241,X'S) H   ( 243,X'S) 
RIDE C   ( 114,X'S) H   (1142,X'S) H   (1141,X'S) H   (1143,X'S) 
END                                                                             
;

_iucr_refine_instructions_details_restraints 
;
#
# Punched on 28/07/16 at 15:58:22
#
#LIST     16                                                                    
SAME N(11)  O(13)  C(14) AND 
CONT N(11)  O(113)  C(114) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
VIBR .0, 0.00200 = N(11) TO O(13) 
VIBR .0, 0.00500 = C(12) TO C(9) 
VIBR .0, 0.00500 = O(13) TO C(9) 
VIBR .0, 0.00500 = O(13) TO C(12) 
VIBR .0, 0.00200 = N(11) TO C(12) 
VIBR .0, 0.00200 = N(11) TO O(113) 
VIBR .0, 0.00500 = O(113) TO C(9) 
VIBR .0, 0.00500 = O(113) TO C(12) 
VIBR .0, 0.00200 = O(13) TO C(14) 
VIBR .0, 0.00500 = C(14) TO N(11) 
VIBR .0, 0.00200 = O(113) TO C(114) 
VIBR .0, 0.00500 = C(114) TO N(11) 
U(IJ) .0, 0.04000 = N(11) TO O(13) 
U(IJ) .0, 0.04000 = N(11) TO O(113) 
U(IJ) .0, 0.08000 = O(13) TO C(14) 
U(IJ) .0, 0.08000 = O(113) TO C(114) 
END                                                                             
;
####################################################################### 
# 
# 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_28
_database_code_depnum_ccdc_archive 'CCDC 1817420'
_audit_update_record             
;
2018-01-16 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;
#==============================================================================
_audit_creation_date             2018-01-15
_audit_creation_method           CRYSTALS_ver_14.61_build_6720

_oxford_structure_analysis_title 6604
_chemical_name_systematic        .
_chemical_melting_point          419

_diffrn_special_details          
;
Initial examination during data collection indicated the presence of 
additional features initially ascribed to either twinning or modulation. 
Upon inspection of data it was possible to identify a reliable q-vector 
of (0.1577(7), 0, 0) that satisfactorily described the diffraction 
pattern. Though a q-vector could be determined, the intensities of the 
satellite reflections were so weak that they could not be used in 
refinement. Hence only main reflections were chosen and the data 
reduced for structure solution and refinement. For 
further details see  '_refine_special_details'
;

_refine_special_details          
;
During refinement disorder were observed that potentially could have 
been solved by taking into account the satellite reflections. 
The presence of satellite reflections indicates that there are a potential 
ordering to the observed disorder. Unstable atoms during refinement,
has been modelled with isotropic thermal parameters. 
;

_cell_length_a                   8.55340(10)
_cell_length_b                   13.2093(2)
_cell_length_c                   16.1337(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1822.86(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

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 0.0181 0.0091 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'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 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 0.0492 0.0322 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            4

# Given Formula = C15 H24 I0.50 N2 O7 
# Dc =      1.49 Fooo =    842.00 Mu =     75.02 M =    407.82
# Found Formula = C15.00 H23.00 I1 N2.00 O6 
# Dc =      1.66 FOOO =    912.00 Mu =    140.95 M =    454.26

_chemical_formula_sum            'C15 H23 I1 N2 O6'
_chemical_formula_moiety         'C15 H23 I1 N2 O6'
_chemical_compound_source        .
_chemical_formula_weight         454.26


_cell_measurement_reflns_used    29438
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.35

_exptl_crystal_density_diffrn    1.655
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    14.095

# Sheldrick geometric approximatio 0.06 0.24 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.08
_exptl_absorpt_correction_T_max  0.24
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_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      150
_diffrn_reflns_number            44993
_reflns_number_total             3811
_diffrn_reflns_av_R_equivalents  0.071
_diffrn_reflns_av_sigmaI/netI    0.0433
# Number of reflections without Friedels Law is 3811 
# Number of reflections with Friedels Law is 2210 
# Theoretical number of reflections is about 1911 

_diffrn_reflns_theta_min         4.326
_diffrn_reflns_theta_max         76.318
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        76.318
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              16
_reflns_limit_l_min              0
_reflns_limit_l_max              20

_oxford_diffrn_Wilson_B_factor   2.58
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -1.03
_refine_diff_density_max         0.60


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


# The values actually used during refinement 
_oxford_refine_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_restraints     27
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3797
_oxford_refine_ls_R_factor_ref   0.0302
_refine_ls_wR_factor_ref         0.0805
_refine_ls_goodness_of_fit_ref   1.0052
_refine_ls_shift/su_max          0.0005260
_refine_ls_shift/su_mean         0.0000348


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3797
_refine_ls_R_factor_all          0.0302
_refine_ls_wR_factor_all         0.0805

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3766
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_gt          0.0803

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661--683 
_oxford_Hooft_y                  0.023(4) # for 1617 Friedel pairs 
_oxford_Bijvoet_difference       0.0197(14) # for 1617 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.026(6) # for 1601 Friedel pairs 
_refine_ls_abs_structure_Flack   0.0197(14)
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 1617 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) + ( 0.06P)² + 1.56P] 
 ,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
N1 N 0.3424(3) 0.43311(19) 0.46931(15) 0.0231 1.0000 Uani . . . . . .
C2 C 0.4039(4) 0.4641(2) 0.55094(17) 0.0263 1.0000 Uani . . . . . .
O3 O 0.2671(3) 0.47611(18) 0.60017(13) 0.0342 1.0000 Uani . . . . . .
C4 C 0.1396(4) 0.4225(2) 0.5634(2) 0.0305 1.0000 Uani . . . . . .
C5 C 0.1711(4) 0.4284(2) 0.47049(19) 0.0231 1.0000 Uani . . . . . .
C6 C 0.1387(4) 0.3307(2) 0.42122(17) 0.0239 1.0000 Uani . . . . . .
C7 C 0.2750(4) 0.3235(2) 0.36122(16) 0.0255 1.0000 Uani . . . . . .
C8 C 0.4069(5) 0.3621(2) 0.41811(18) 0.0269 1.0000 Uani . . . . . .
O8 O 0.5420(3) 0.3339(2) 0.4189(2) 0.0449 1.0000 Uani . . . . . .
C9 C 0.3244(9) 0.2192(6) 0.3303(4) 0.0221(18) 0.538(7) Uiso . . P 1 1 .
C109 C 0.2888(9) 0.2137(6) 0.3327(5) 0.0171(19) 0.462(7) Uiso . . P 1 2 .
O10 O 0.2749(6) 0.1424(4) 0.3770(3) 0.0315(12) 0.538(7) Uiso . . P 1 1 .
O110 O 0.2423(6) 0.1441(4) 0.3554(4) 0.0265(13) 0.462(7) Uiso . . P 1 2 .
N11 N 0.4175(14) 0.2122(11) 0.2647(10) 0.0297 0.538(7) Uani . . P 1 1 .
N111 N 0.3681(16) 0.2008(15) 0.2591(12) 0.0371 0.462(7) Uani . . P 1 2 .
C12 C 0.4815(15) 0.1135(6) 0.2386(5) 0.0446 0.538(7) Uani . . P 1 1 .
C112 C 0.3813(17) 0.1030(9) 0.2217(7) 0.0540 0.462(7) Uani . . P 1 2 .
O13 O 0.5152(6) 0.2938(4) 0.2479(3) 0.0313 0.538(7) Uani . . P 1 1 .
O113 O 0.3616(8) 0.2832(6) 0.2036(3) 0.0468 0.462(7) Uani . . P 1 2 .
C14 C 0.478(3) 0.3349(16) 0.1686(12) 0.0507 0.538(7) Uani . . P 1 1 .
C114 C 0.518(3) 0.3217(17) 0.1892(13) 0.0545 0.462(7) Uani . . P 1 2 .
I15 I -0.09334(3) 0.324531(16) 0.371666(15) 0.0377 1.0000 Uani . . . . . .
C16 C 0.0943(18) 0.5251(11) 0.4218(13) 0.0202 0.363(18) Uani D . P 2 1 .
C116 C 0.1045(11) 0.5233(7) 0.4364(8) 0.0283 0.637(18) Uani D . P 2 2 .
O17 O -0.0040(19) 0.5766(13) 0.4540(10) 0.0357 0.363(18) Uani D . P 2 1 .
O117 O 0.0244(9) 0.5839(7) 0.4719(6) 0.0319 0.637(18) Uani D . P 2 2 .
O18 O 0.152(2) 0.5399(19) 0.3456(14) 0.0337 0.363(18) Uani D . P 2 1 .
O118 O 0.1497(11) 0.5306(10) 0.3567(8) 0.0337 0.637(18) Uani D . P 2 2 .
C19 C 0.073(4) 0.615(3) 0.2951(13) 0.0490 0.363(18) Uani D . P 2 1 .
C119 C 0.0950(15) 0.6190(13) 0.3115(7) 0.0490 0.637(18) Uani D . P 2 2 .
C20 C 0.4954(5) 0.5642(2) 0.5507(2) 0.0300 1.0000 Uani . . . . . .
C21 C 0.3986(5) 0.6508(2) 0.5151(2) 0.0375 1.0000 Uani . . . . . .
C22 C 0.5382(6) 0.5864(3) 0.6418(2) 0.0432 1.0000 Uani . . . . . .
C23 C 0.6449(5) 0.5493(3) 0.5013(3) 0.0403 1.0000 Uani . . . . . .
H21 H 0.4714 0.4099 0.5728 0.0319 1.0000 Uiso . . . . . .
H41 H 0.1382 0.3528 0.5812 0.0369 1.0000 Uiso . . . . . .
H42 H 0.0399 0.4547 0.5765 0.0366 1.0000 Uiso . . . . . .
H61 H 0.1462 0.2746 0.4600 0.0298 1.0000 Uiso . . . . . .
H121 H 0.4737 0.1064 0.1794 0.0668 0.538(7) Uiso . . P 1 1 .
H123 H 0.4263 0.0590 0.2642 0.0669 0.538(7) Uiso . . P 1 1 .
H122 H 0.5897 0.1086 0.2542 0.0670 0.538(7) Uiso . . P 1 1 .
H141 H 0.5554 0.3838 0.1532 0.0760 0.538(7) Uiso . . P 1 1 .
H142 H 0.4751 0.2814 0.1284 0.0759 0.538(7) Uiso . . P 1 1 .
H143 H 0.3776 0.3673 0.1709 0.0759 0.538(7) Uiso . . P 1 1 .
H1141 H 0.5109 0.3847 0.1596 0.0820 0.462(7) Uiso . . P 1 2 .
H1142 H 0.5754 0.2737 0.1569 0.0820 0.462(7) Uiso . . P 1 2 .
H1143 H 0.5697 0.3326 0.2414 0.0820 0.462(7) Uiso . . P 1 2 .
H191 H 0.0943 0.6023 0.2377 0.0740 0.363(18) Uiso . . P 2 1 .
H193 H -0.0373 0.6111 0.3052 0.0740 0.363(18) Uiso . . P 2 1 .
H192 H 0.1100 0.6811 0.3102 0.0740 0.363(18) Uiso . . P 2 1 .
H1191 H 0.1275 0.6143 0.2547 0.0739 0.637(18) Uiso . . P 2 2 .
H1193 H -0.0170 0.6215 0.3149 0.0738 0.637(18) Uiso . . P 2 2 .
H1192 H 0.1376 0.6786 0.3364 0.0740 0.637(18) Uiso . . P 2 2 .
H211 H 0.4574 0.7119 0.5166 0.0558 1.0000 Uiso . . . . . .
H212 H 0.3728 0.6367 0.4585 0.0559 1.0000 Uiso . . . . . .
H213 H 0.3043 0.6595 0.5456 0.0561 1.0000 Uiso . . . . . .
H221 H 0.6069 0.6439 0.6451 0.0646 1.0000 Uiso . . . . . .
H222 H 0.5900 0.5301 0.6666 0.0650 1.0000 Uiso . . . . . .
H223 H 0.4454 0.6009 0.6732 0.0651 1.0000 Uiso . . . . . .
H71 H 0.2592 0.3685 0.3143 0.0312 1.0000 Uiso . . . . . .
H231 H 0.7090 0.6089 0.5054 0.0601 1.0000 Uiso . . . . . .
H232 H 0.7017 0.4926 0.5237 0.0600 1.0000 Uiso . . . . . .
H233 H 0.6214 0.5361 0.4443 0.0597 1.0000 Uiso . . . . . .
H1121 H 0.3286 0.1037 0.1691 0.0810 0.462(7) Uiso . . P 1 2 .
H1122 H 0.4890 0.0866 0.2129 0.0809 0.462(7) Uiso . . P 1 2 .
H1123 H 0.3342 0.0524 0.2562 0.0810 0.462(7) Uiso . . P 1 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.85(7)
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
N1 . C2 . 1.476(4) yes
N1 . C5 . 1.466(4) yes
N1 . C8 . 1.366(4) yes
C2 . O3 . 1.423(4) yes
C2 . C20 . 1.537(4) yes
C2 . H21 . 0.984 no
O3 . C4 . 1.429(4) yes
C4 . C5 . 1.525(4) yes
C4 . H41 . 0.965 no
C4 . H42 . 0.975 no
C5 . C6 . 1.541(4) yes
C5 . C16 . 1.638(17) yes
C5 . C6 . 1.541(4) yes
C5 . C116 . 1.483(10) yes
C6 . C7 . 1.518(4) yes
C6 . I15 . 2.141(3) yes
C6 . H61 . 0.973 no
C7 . C8 . 1.541(4) yes
C7 . C9 . 1.525(8) yes
C7 . H71 . 0.972 no
C7 . C8 . 1.541(4) yes
C7 . C109 . 1.527(8) yes
C7 . H71 . 0.972 no
C8 . O8 . 1.214(5) yes
C9 . O10 . 1.333(9) yes
C9 . N11 . 1.33(2) yes
C109 . O110 . 1.067(10) yes
C109 . N111 . 1.38(2) yes
N11 . C12 . 1.476(18) yes
N11 . O13 . 1.391(13) yes
N111 . C112 . 1.43(2) yes
N111 . O113 . 1.410(19) yes
C12 . H121 . 0.962 no
C12 . H123 . 0.955 no
C12 . H122 . 0.961 no
C112 . H1121 . 0.960 no
C112 . H1122 . 0.958 no
C112 . H1123 . 0.959 no
O13 . C14 . 1.425(14) yes
O113 . C114 . 1.45(2) yes
C14 . H141 . 0.958 no
C14 . H142 . 0.959 no
C14 . H143 . 0.960 no
C114 . H1141 . 0.960 no
C114 . H1142 . 0.957 no
C114 . H1143 . 0.963 no
C16 . O17 . 1.199(9) yes
C16 . O18 . 1.339(9) yes
C116 . O117 . 1.199(7) yes
C116 . O118 . 1.345(6) yes
O18 . C19 . 1.452(9) yes
O118 . C119 . 1.455(6) yes
C19 . H191 . 0.958 no
C19 . H193 . 0.959 no
C19 . H192 . 0.959 no
C119 . H1191 . 0.959 no
C119 . H1193 . 0.960 no
C119 . H1192 . 0.957 no
C20 . C21 . 1.524(5) yes
C20 . C22 . 1.543(5) yes
C20 . C23 . 1.519(6) yes
C21 . H211 . 0.952 no
C21 . H212 . 0.957 no
C21 . H213 . 0.952 no
C22 . H221 . 0.962 no
C22 . H222 . 0.953 no
C22 . H223 . 0.961 no
C23 . H231 . 0.961 no
C23 . H232 . 0.963 no
C23 . H233 . 0.957 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 . N1 . C5 . 110.9(2) yes
C2 . N1 . C8 . 125.8(3) yes
C5 . N1 . C8 . 112.5(3) yes
N1 . C2 . O3 . 103.7(3) yes
N1 . C2 . C20 . 114.7(2) yes
O3 . C2 . C20 . 108.9(3) yes
N1 . C2 . H21 . 109.1 no
O3 . C2 . H21 . 111.3 no
C20 . C2 . H21 . 109.1 no
C2 . O3 . C4 . 109.9(2) yes
O3 . C4 . C5 . 104.3(2) yes
O3 . C4 . H41 . 111.0 no
C5 . C4 . H41 . 110.1 no
O3 . C4 . H42 . 111.2 no
C5 . C4 . H42 . 110.2 no
H41 . C4 . H42 . 109.9 no
C4 . C5 . N1 . 101.0(3) yes
C4 . C5 . C6 . 115.6(2) yes
N1 . C5 . C6 . 102.0(2) yes
C4 . C5 . C16 . 116.1(8) yes
N1 . C5 . C16 . 111.2(6) yes
C6 . C5 . C16 . 109.5(5) yes
C4 . C5 . N1 . 101.0(3) yes
C4 . C5 . C6 . 115.6(2) yes
N1 . C5 . C6 . 102.0(2) yes
C4 . C5 . C116 . 109.9(6) yes
N1 . C5 . C116 . 110.1(4) yes
C6 . C5 . C116 . 116.6(4) yes
C5 . C6 . C7 . 104.0(2) yes
C5 . C6 . I15 . 113.0(2) yes
C7 . C6 . I15 . 118.12(18) yes
C5 . C6 . H61 . 107.1 no
C7 . C6 . H61 . 108.2 no
I15 . C6 . H61 . 105.8 no
C6 . C7 . C8 . 99.3(2) yes
C6 . C7 . C9 . 118.5(4) yes
C8 . C7 . C9 . 106.9(3) yes
C6 . C7 . H71 . 110.6 no
C8 . C7 . H71 . 111.4 no
C9 . C7 . H71 . 109.6 no
C6 . C7 . C8 . 99.3(2) yes
C6 . C7 . C109 . 108.1(4) yes
C8 . C7 . C109 . 115.9(3) yes
C6 . C7 . H71 . 110.6 no
C8 . C7 . H71 . 111.4 no
C109 . C7 . H71 . 110.9 no
C7 . C8 . N1 . 106.9(3) yes
C7 . C8 . O8 . 127.0(3) yes
N1 . C8 . O8 . 126.1(3) yes
C7 . C9 . O10 . 114.5(6) yes
C7 . C9 . N11 . 119.4(8) yes
O10 . C9 . N11 . 126.0(8) yes
C7 . C109 . O110 . 133.4(7) yes
C7 . C109 . N111 . 114.5(10) yes
O110 . C109 . N111 . 111.9(10) yes
C9 . N11 . C12 . 120.8(11) yes
C9 . N11 . O13 . 117.5(12) yes
C12 . N11 . O13 . 113.9(12) yes
C109 . N111 . C112 . 120.9(14) yes
C109 . N111 . O113 . 115.6(15) yes
C112 . N111 . O113 . 115.6(15) yes
N11 . C12 . H121 . 110.0 no
N11 . C12 . H123 . 111.0 no
H121 . C12 . H123 . 108.9 no
N11 . C12 . H122 . 109.9 no
H121 . C12 . H122 . 108.7 no
H123 . C12 . H122 . 108.2 no
N111 . C112 . H1121 . 109.1 no
N111 . C112 . H1122 . 110.1 no
H1121 . C112 . H1122 . 108.8 no
N111 . C112 . H1123 . 110.6 no
H1121 . C112 . H1123 . 108.8 no
H1122 . C112 . H1123 . 109.4 no
N11 . O13 . C14 . 109.6(12) yes
N111 . O113 . C114 . 109.7(10) yes
O13 . C14 . H141 . 109.7 no
O13 . C14 . H142 . 109.4 no
H141 . C14 . H142 . 109.8 no
O13 . C14 . H143 . 109.6 no
H141 . C14 . H143 . 109.2 no
H142 . C14 . H143 . 109.3 no
O113 . C114 . H1141 . 109.1 no
O113 . C114 . H1142 . 109.2 no
H1141 . C114 . H1142 . 109.6 no
O113 . C114 . H1143 . 109.7 no
H1141 . C114 . H1143 . 109.4 no
H1142 . C114 . H1143 . 109.8 no
C5 . C16 . O17 . 121.1(15) yes
C5 . C16 . O18 . 114.0(15) yes
O17 . C16 . O18 . 124.97(10) yes
C5 . C116 . O117 . 127.3(9) yes
C5 . C116 . O118 . 107.7(9) yes
O117 . C116 . O118 . 124.97(10) yes
C16 . O18 . C19 . 116.36(10) yes
C116 . O118 . C119 . 116.37(10) yes
O18 . C19 . H191 . 109.5 no
O18 . C19 . H193 . 108.9 no
H191 . C19 . H193 . 110.0 no
O18 . C19 . H192 . 109.0 no
H191 . C19 . H192 . 110.2 no
H193 . C19 . H192 . 109.3 no
O118 . C119 . H1191 . 109.5 no
O118 . C119 . H1193 . 108.6 no
H1191 . C119 . H1193 . 110.3 no
O118 . C119 . H1192 . 109.1 no
H1191 . C119 . H1192 . 110.2 no
H1193 . C119 . H1192 . 109.1 no
C2 . C20 . C21 . 111.7(3) yes
C2 . C20 . C22 . 106.4(3) yes
C21 . C20 . C22 . 110.2(3) yes
C2 . C20 . C23 . 108.6(3) yes
C21 . C20 . C23 . 110.9(3) yes
C22 . C20 . C23 . 108.9(3) yes
C20 . C21 . H211 . 109.9 no
C20 . C21 . H212 . 109.8 no
H211 . C21 . H212 . 108.0 no
C20 . C21 . H213 . 110.9 no
H211 . C21 . H213 . 109.4 no
H212 . C21 . H213 . 108.7 no
C20 . C22 . H221 . 110.3 no
C20 . C22 . H222 . 111.2 no
H221 . C22 . H222 . 108.0 no
C20 . C22 . H223 . 110.1 no
H221 . C22 . H223 . 108.5 no
H222 . C22 . H223 . 108.6 no
C20 . C23 . H231 . 109.8 no
C20 . C23 . H232 . 109.2 no
H231 . C23 . H232 . 108.9 no
C20 . C23 . H233 . 110.5 no
H231 . C23 . H233 . 109.5 no
H232 . C23 . H233 . 108.9 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 . O8 3_456 155 0.96 2.60 3.500(13) yes
C6 . H61 . O8 3_456 153 0.97 2.58 3.474(13) yes
C23 . H232 . O10 3_556 158 0.96 2.48 3.391(13) yes


