# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_1
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6202
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   5.2735(2)
_cell_length_b                   8.6164(4)
_cell_length_c                   9.3766(4)
_cell_angle_alpha                97.6974(18)
_cell_angle_beta                 93.5064(18)
_cell_angle_gamma                95.8677(19)
_cell_volume                     418.80(3)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-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'


_cell_formula_units_Z            2

# Given Formula = C8 H13 N1 O3 
# Dc =      1.36 Fooo =    184.00 Mu =      1.04 M =    171.20
# Found Formula = C8 H13 N1 O3 
# Dc =      1.36 FOOO =    184.00 Mu =      1.04 M =    171.20

_chemical_formula_sum            'C8 H13 N1 O3'
_chemical_formula_moiety         'C8 H13 N1 O3'
_chemical_compound_source        .
_chemical_formula_weight         171.20


_cell_measurement_reflns_used    1801
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       needle
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.67

_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             184
_exptl_absorpt_coefficient_mu    0.104

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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            7659
_reflns_number_total             1882
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 3299 
# Number of reflections with Friedels Law is 1882 
# Theoretical number of reflections is about 1151 


_diffrn_reflns_theta_min         5.304
_diffrn_reflns_theta_max         27.408
_diffrn_measured_fraction_theta_max 0.986

_diffrn_reflns_theta_full        26.312
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   1.63
_oxford_diffrn_Wilson_scale      1.72

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

_refine_diff_density_min         -0.28
_refine_diff_density_max         0.28


# 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         1135
_refine_ls_number_restraints     0
_refine_ls_number_parameters     109
_oxford_refine_ls_R_factor_ref   0.0522
_refine_ls_wR_factor_ref         0.1240
_refine_ls_goodness_of_fit_ref   0.9467
_refine_ls_shift/su_max          0.0001954
_refine_ls_shift/su_mean         0.0000590


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1135
_refine_ls_R_factor_all          0.0522
_refine_ls_wR_factor_all         0.1240

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                918
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_gt          0.1079

# 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 .


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 16.4 25.4 12.6 3.39 
;

# 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 1.0226(3) 0.19723(17) 1.02609(16) 0.0308 1.0000 Uani . . . . . .
O2 O 0.4991(3) -0.21947(17) 0.74492(18) 0.0348 1.0000 Uani . . . . . .
O3 O 0.1411(3) -0.13127(17) 0.66194(16) 0.0289 1.0000 Uani . . . . . .
C1 C 0.8166(4) 0.1983(2) 0.9558(2) 0.0230 1.0000 Uani . . . . . .
C2 C 0.6922(4) 0.3480(2) 0.9557(2) 0.0252 1.0000 Uani . . . . . .
C3 C 0.6962(4) 0.4104(2) 0.8097(2) 0.0259 1.0000 Uani . . . . . .
C4 C 0.4808(4) 0.3316(3) 0.7007(2) 0.0288 1.0000 Uani . . . . . .
C5 C 0.4792(4) 0.1544(2) 0.6583(2) 0.0272 1.0000 Uani . . . . . .
C6 C 0.4583(4) 0.0588(2) 0.7861(2) 0.0232 1.0000 Uani . . . . . .
C7 C 0.3742(4) -0.1128(2) 0.7308(2) 0.0241 1.0000 Uani . . . . . .
C8 C 0.0382(4) -0.2922(3) 0.6122(3) 0.0325 1.0000 Uani . . . . . .
N1 N 0.6981(3) 0.06751(19) 0.87403(18) 0.0241 1.0000 Uani . . . . . .
H11 H 0.7608 -0.0183 0.8809 0.0278 1.0000 Uiso R . . . . .
H21 H 0.7892 0.4295 1.0344 0.0296 1.0000 Uiso R . . . . .
H22 H 0.5124 0.3286 0.9843 0.0306 1.0000 Uiso R . . . . .
H31 H 0.8588 0.3929 0.7687 0.0318 1.0000 Uiso R . . . . .
H32 H 0.6864 0.5255 0.8237 0.0312 1.0000 Uiso R . . . . .
H41 H 0.4969 0.3800 0.6122 0.0315 1.0000 Uiso R . . . . .
H42 H 0.3228 0.3476 0.7396 0.0324 1.0000 Uiso R . . . . .
H51 H 0.6368 0.1310 0.6131 0.0313 1.0000 Uiso R . . . . .
H52 H 0.3277 0.1124 0.5885 0.0317 1.0000 Uiso R . . . . .
H61 H 0.3282 0.0982 0.8471 0.0265 1.0000 Uiso R . . . . .
H81 H 0.1208 -0.3345 0.5283 0.0516 1.0000 Uiso R . . . . .
H82 H 0.0648 -0.3531 0.6886 0.0522 1.0000 Uiso R . . . . .
H83 H -0.1409 -0.2919 0.5925 0.0496 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0292(9) 0.0287(9) 0.0330(8) 0.0013(6) -0.0067(7) 0.0059(6)
O2 0.0304(9) 0.0245(9) 0.0489(10) 0.0037(7) -0.0040(7) 0.0054(7)
O3 0.0257(8) 0.0258(8) 0.0339(8) 0.0042(6) -0.0041(6) 0.0005(6)
C1 0.0235(12) 0.0247(11) 0.0211(10) 0.0043(8) 0.0030(9) 0.0031(8)
C2 0.0257(12) 0.0229(11) 0.0267(11) 0.0008(9) 0.0012(9) 0.0044(9)
C3 0.0278(11) 0.0199(11) 0.0306(12) 0.0035(9) 0.0047(9) 0.0045(8)
C4 0.0302(12) 0.0283(12) 0.0301(11) 0.0109(9) 0.0016(9) 0.0060(9)
C5 0.0301(12) 0.0256(12) 0.0255(11) 0.0040(9) -0.0008(9) 0.0027(9)
C6 0.0207(11) 0.0261(12) 0.0230(11) 0.0043(9) 0.0015(8) 0.0030(9)
C7 0.0219(11) 0.0265(12) 0.0241(11) 0.0043(9) 0.0032(9) 0.0013(9)
C8 0.0293(12) 0.0276(12) 0.0381(13) 0.0027(10) -0.0001(10) -0.0054(10)
N1 0.0233(10) 0.0196(9) 0.0297(10) 0.0038(7) -0.0006(7) 0.0050(7)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.823(6)
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 . C1 . 1.237(2) yes
O2 . C7 . 1.201(3) yes
O3 . C7 . 1.337(2) yes
O3 . C8 . 1.441(3) yes
C1 . C2 . 1.506(3) yes
C1 . N1 . 1.347(3) yes
C2 . C3 . 1.537(3) yes
C2 . H21 . 1.020 no
C2 . H22 . 1.005 no
C3 . C4 . 1.520(3) yes
C3 . H31 . 0.978 no
C3 . H32 . 0.990 no
C4 . C5 . 1.524(3) yes
C4 . H41 . 0.981 no
C4 . H42 . 0.945 no
C5 . C6 . 1.545(3) yes
C5 . H51 . 0.983 no
C5 . H52 . 1.006 no
C6 . C7 . 1.511(3) yes
C6 . N1 . 1.457(3) yes
C6 . H61 . 0.978 no
C8 . H81 . 0.969 no
C8 . H82 . 0.955 no
C8 . H83 . 0.952 no
N1 . H11 . 0.849 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
C7 . O3 . C8 . 115.17(16) yes
O1 . C1 . C2 . 120.91(18) yes
O1 . C1 . N1 . 121.63(19) yes
C2 . C1 . N1 . 117.45(18) yes
C1 . C2 . C3 . 112.78(16) yes
C1 . C2 . H21 . 107.1 no
C3 . C2 . H21 . 109.9 no
C1 . C2 . H22 . 108.6 no
C3 . C2 . H22 . 111.1 no
H21 . C2 . H22 . 107.1 no
C2 . C3 . C4 . 113.46(17) yes
C2 . C3 . H31 . 108.9 no
C4 . C3 . H31 . 108.3 no
C2 . C3 . H32 . 110.0 no
C4 . C3 . H32 . 108.8 no
H31 . C3 . H32 . 107.2 no
C3 . C4 . C5 . 115.59(17) yes
C3 . C4 . H41 . 107.6 no
C5 . C4 . H41 . 107.1 no
C3 . C4 . H42 . 108.8 no
C5 . C4 . H42 . 106.8 no
H41 . C4 . H42 . 110.9 no
C4 . C5 . C6 . 114.17(17) yes
C4 . C5 . H51 . 110.4 no
C6 . C5 . H51 . 107.0 no
C4 . C5 . H52 . 109.9 no
C6 . C5 . H52 . 106.0 no
H51 . C5 . H52 . 109.1 no
C5 . C6 . C7 . 110.07(16) yes
C5 . C6 . N1 . 113.17(16) yes
C7 . C6 . N1 . 107.82(16) yes
C5 . C6 . H61 . 108.9 no
C7 . C6 . H61 . 107.8 no
N1 . C6 . H61 . 108.9 no
C6 . C7 . O3 . 111.07(17) yes
C6 . C7 . O2 . 125.09(18) yes
O3 . C7 . O2 . 123.84(19) yes
O3 . C8 . H81 . 110.8 no
O3 . C8 . H82 . 108.5 no
H81 . C8 . H82 . 109.9 no
O3 . C8 . H83 . 106.7 no
H81 . C8 . H83 . 112.5 no
H82 . C8 . H83 . 108.4 no
C6 . N1 . C1 . 125.29(17) yes
C6 . N1 . H11 . 117.4 no
C1 . N1 . H11 . 117.1 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
N1 . H11 . O1 2_757 159.93 0.849 2.245 3.056(3) yes
C6 . H61 . O1 1_455 174.24 0.978 2.524 3.498(3) yes
C8 . H83 . O2 1_455 134.01 0.952 2.524 3.258(3) yes
_database_code_depnum_ccdc_archive 'CCDC 1018875'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_2
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6323
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   10.5713(8)
_cell_length_b                   10.6265(5)
_cell_length_c                   11.0705(7)
_cell_angle_alpha                72.339(5)
_cell_angle_beta                 78.005(6)
_cell_angle_gamma                80.552(5)
_cell_volume                     1152.29(13)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-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 0.0181 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            6

# Given Formula = C7 H11 N1 O3 
# Dc =      1.36 Fooo =    504.00 Mu =      8.96 M =    471.51
# Found Formula = C7 H11 N1 O3 
# Dc =      1.36 FOOO =    504.00 Mu =      8.96 M =    471.51

_chemical_formula_sum            'C7 H11 N1 O3'
_chemical_formula_moiety         'C7 H11 N1 O3'
_chemical_compound_source        .
_chemical_formula_weight         157.17


_cell_measurement_reflns_used    4235
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    0.896

# Sheldrick geometric approximatio 0.91 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_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  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    'SIR92 (Altomare et al., 1994)'
_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            10066
_reflns_number_total             4752
_diffrn_reflns_av_R_equivalents  0.023
# Number of reflections with Friedels Law is 4752 
# Theoretical number of reflections is about 7316 


_diffrn_reflns_theta_min         4.252
_diffrn_reflns_theta_max         76.407
_diffrn_measured_fraction_theta_max 0.981

_diffrn_reflns_theta_full        73.351
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              -12
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.51
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.32
_refine_diff_density_max         1.03


# 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         3662
_refine_ls_number_restraints     0
_refine_ls_number_parameters     298
_oxford_refine_ls_R_factor_ref   0.0631
_refine_ls_wR_factor_ref         0.1568
_refine_ls_goodness_of_fit_ref   0.9925
_refine_ls_shift/su_max          0.0003122
_refine_ls_shift/su_mean         0.0000346


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3662
_refine_ls_R_factor_all          0.0631
_refine_ls_wR_factor_all         0.1568

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3278
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_gt          0.1518

# 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 .


_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) + ( 0.09P)² + 1.15P] 
 ,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 -0.05638(18) 0.55009(19) 1.34254(17) 0.0429 1.0000 Uani . . . . . .
O2 O 0.1609(2) 0.57921(18) 0.92949(17) 0.0481 1.0000 Uani . . . . . .
O3 O 0.2821(2) 0.39027(17) 0.91498(17) 0.0428 1.0000 Uani . . . . . .
O11 O 0.34378(18) 0.49903(17) 0.67424(17) 0.0406 1.0000 Uani . . . . . .
O12 O 0.0575(2) 0.85516(18) 0.76570(18) 0.0524 1.0000 Uani . . . . . .
O13 O 0.07184(18) 1.03457(16) 0.59771(16) 0.0370 1.0000 Uani . . . . . .
O21 O -0.11999(18) 1.14735(17) 0.72353(17) 0.0403 1.0000 Uani . . . . . .
O22 O -0.04077(18) 0.77041(17) 1.05151(16) 0.0380 1.0000 Uani . . . . . .
O23 O -0.1612(2) 0.7805(2) 1.23930(17) 0.0508 1.0000 Uani . . . . . .
C1 C 0.0278(2) 0.4678(2) 1.3037(2) 0.0328 1.0000 Uani . . . . . .
C2 C 0.0688(3) 0.3396(2) 1.3986(2) 0.0361 1.0000 Uani . . . . . .
C3 C 0.2113(3) 0.3232(3) 1.4132(2) 0.0377 1.0000 Uani . . . . . .
C4 C 0.3048(3) 0.2753(3) 1.3079(3) 0.0425 1.0000 Uani . . . . . .
C5 C 0.3093(3) 0.3721(3) 1.1734(2) 0.0377 1.0000 Uani . . . . . .
C6 C 0.1797(2) 0.4022(2) 1.1226(2) 0.0321 1.0000 Uani . . . . . .
C7 C 0.2055(2) 0.4676(2) 0.9783(2) 0.0332 1.0000 Uani . . . . . .
C11 C 0.3131(2) 0.6116(2) 0.6031(2) 0.0307 1.0000 Uani . . . . . .
C12 C 0.3648(2) 0.6451(2) 0.4616(2) 0.0318 1.0000 Uani . . . . . .
C13 C 0.4686(3) 0.7428(3) 0.4202(3) 0.0373 1.0000 Uani . . . . . .
C14 C 0.4135(3) 0.8877(2) 0.4058(3) 0.0388 1.0000 Uani . . . . . .
C15 C 0.3313(3) 0.9168(2) 0.5267(2) 0.0349 1.0000 Uani . . . . . .
C16 C 0.2093(2) 0.8421(2) 0.5750(2) 0.0285 1.0000 Uani . . . . . .
C17 C 0.1043(2) 0.9107(2) 0.6574(2) 0.0300 1.0000 Uani . . . . . .
C21 C -0.1660(3) 1.1225(3) 0.8398(2) 0.0378 1.0000 Uani . . . . . .
C22 C -0.2507(3) 1.2304(3) 0.8905(3) 0.0431 1.0000 Uani . . . . . .
C23 C -0.3902(3) 1.1984(3) 0.9428(3) 0.0499 1.0000 Uani . . . . . .
C24 C -0.4086(3) 1.1066(3) 1.0803(3) 0.0519 1.0000 Uani . . . . . .
C25 C -0.3349(3) 0.9672(3) 1.0946(3) 0.0450 1.0000 Uani . . . . . .
C26 C -0.1899(3) 0.9650(3) 1.0596(2) 0.0376 1.0000 Uani . . . . . .
C27 C -0.1226(3) 0.8268(3) 1.1158(2) 0.0354 1.0000 Uani . . . . . .
N1 N 0.0847(2) 0.49284(19) 1.18059(19) 0.0311 1.0000 Uani . . . . . .
N11 N 0.2376(2) 0.70535(19) 0.65012(19) 0.0312 1.0000 Uani . . . . . .
N21 N -0.1437(2) 1.0025(2) 0.92158(19) 0.0323 1.0000 Uani . . . . . .
H11 H 0.0588 0.5656 1.1294 0.0372 1.0000 Uiso R . . . . .
H21 H 0.0139 0.3363 1.4806 0.0425 1.0000 Uiso R . . . . .
H22 H 0.0529 0.2661 1.3713 0.0426 1.0000 Uiso R . . . . .
H31 H 0.2965 0.4342 0.8366 0.0645 1.0000 Uiso R . . . . .
H32 H 0.2201 0.2570 1.4947 0.0449 1.0000 Uiso R . . . . .
H41 H 0.3912 0.2569 1.3295 0.0512 1.0000 Uiso R . . . . .
H42 H 0.2752 0.1942 1.3057 0.0505 1.0000 Uiso R . . . . .
H51 H 0.3377 0.4559 1.1730 0.0444 1.0000 Uiso R . . . . .
H52 H 0.3730 0.3338 1.1135 0.0450 1.0000 Uiso R . . . . .
H61 H 0.1443 0.3177 1.1385 0.0383 1.0000 Uiso R . . . . .
H111 H 0.2070 0.6843 0.7305 0.0368 1.0000 Uiso R . . . . .
H121 H 0.4021 0.5628 0.4413 0.0372 1.0000 Uiso R . . . . .
H122 H 0.2918 0.6834 0.4153 0.0376 1.0000 Uiso R . . . . .
H131 H 0.0142 1.0643 0.6464 0.0563 1.0000 Uiso R . . . . .
H132 H 0.5182 0.7355 0.3373 0.0445 1.0000 Uiso R . . . . .
H141 H 0.4838 0.9428 0.3782 0.0476 1.0000 Uiso R . . . . .
H142 H 0.3587 0.9130 0.3387 0.0464 1.0000 Uiso R . . . . .
H151 H 0.3833 0.8918 0.5955 0.0414 1.0000 Uiso R . . . . .
H152 H 0.3050 1.0117 0.5082 0.0415 1.0000 Uiso R . . . . .
H161 H 0.1732 0.8440 0.4993 0.0331 1.0000 Uiso R . . . . .
H211 H -0.0898 0.9461 0.8921 0.0388 1.0000 Uiso R . . . . .
H221 H -0.2157 1.2456 0.9624 0.0513 1.0000 Uiso R . . . . .
H222 H -0.2490 1.3139 0.8166 0.0519 1.0000 Uiso R . . . . .
H231 H -0.1211 0.7056 1.2654 0.0761 1.0000 Uiso R . . . . .
H232 H -0.4071 1.1543 0.8822 0.0600 1.0000 Uiso R . . . . .
H241 H -0.3677 1.1493 1.1293 0.0558 1.0000 Uiso R . . . . .
H242 H -0.5014 1.1009 1.1161 0.0627 1.0000 Uiso R . . . . .
H251 H -0.3554 0.9153 1.1862 0.0542 1.0000 Uiso R . . . . .
H252 H -0.3637 0.9225 1.0398 0.0536 1.0000 Uiso R . . . . .
H261 H -0.1708 1.0290 1.1028 0.0459 1.0000 Uiso R . . . . .
H262 H 0.5252 0.7174 0.4849 0.0447 1.0000 Uiso R . . . . .
H263 H -0.4452 1.2836 0.9425 0.0601 1.0000 Uiso R . . . . .
H264 H 0.2338 0.4082 1.4142 0.0448 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0447(11) 0.0410(10) 0.0298(9) -0.0034(8) -0.0008(8) 0.0131(8)
O2 0.0690(13) 0.0296(10) 0.0290(9) -0.0011(8) 0.0004(9) 0.0168(9)
O3 0.0598(12) 0.0284(9) 0.0290(9) -0.0049(7) 0.0016(8) 0.0090(8)
O11 0.0502(11) 0.0255(9) 0.0332(9) -0.0028(7) 0.0024(8) 0.0094(8)
O12 0.0681(14) 0.0275(9) 0.0363(11) 0.0008(8) 0.0168(9) 0.0142(9)
O13 0.0468(10) 0.0232(9) 0.0306(9) -0.0036(7) 0.0015(7) 0.0080(7)
O21 0.0467(11) 0.0299(9) 0.0328(10) -0.0036(7) -0.0011(8) 0.0114(8)
O22 0.0421(10) 0.0311(9) 0.0318(9) -0.0056(7) -0.0013(8) 0.0092(8)
O23 0.0658(13) 0.0452(11) 0.0267(9) -0.0067(8) -0.0046(9) 0.0250(10)
C1 0.0335(13) 0.0304(13) 0.0302(13) -0.0050(10) -0.0043(10) 0.0002(10)
C2 0.0437(14) 0.0292(13) 0.0281(12) -0.0012(10) -0.0019(11) -0.0019(11)
C3 0.0455(15) 0.0316(13) 0.0301(13) -0.0029(10) -0.0086(11) 0.0045(11)
C4 0.0454(15) 0.0396(15) 0.0347(14) -0.0051(11) -0.0097(12) 0.0114(12)
C5 0.0363(14) 0.0347(13) 0.0340(13) -0.0054(11) -0.0029(11) 0.0073(11)
C6 0.0411(14) 0.0215(11) 0.0286(12) -0.0042(9) -0.0031(10) 0.0021(10)
C7 0.0399(14) 0.0260(13) 0.0297(13) -0.0065(10) -0.0039(10) 0.0027(10)
C11 0.0317(12) 0.0228(12) 0.0325(13) -0.0052(10) -0.0011(10) 0.0016(9)
C12 0.0350(13) 0.0254(12) 0.0305(12) -0.0075(10) -0.0015(10) 0.0036(10)
C13 0.0349(13) 0.0328(13) 0.0382(14) -0.0099(11) 0.0047(11) -0.0005(10)
C14 0.0389(14) 0.0293(13) 0.0417(14) -0.0079(11) 0.0070(11) -0.0069(11)
C15 0.0385(14) 0.0254(12) 0.0377(13) -0.0074(10) -0.0020(11) -0.0026(10)
C16 0.0341(12) 0.0206(11) 0.0261(11) -0.0036(9) -0.0021(10) 0.0007(9)
C17 0.0364(13) 0.0204(11) 0.0290(12) -0.0038(9) -0.0048(10) 0.0016(9)
C21 0.0418(14) 0.0308(13) 0.0341(14) -0.0073(11) -0.0028(11) 0.0064(11)
C22 0.0454(16) 0.0324(14) 0.0443(15) -0.0087(12) -0.0009(12) 0.0036(11)
C23 0.0443(16) 0.0400(16) 0.0500(17) -0.0023(13) -0.0023(13) 0.0111(12)
C24 0.0411(16) 0.0497(17) 0.0467(17) -0.0044(13) 0.0052(13) 0.0129(13)
C25 0.0420(15) 0.0415(15) 0.0415(15) -0.0030(12) -0.0003(12) -0.0010(12)
C26 0.0447(15) 0.0350(14) 0.0274(12) -0.0107(10) -0.0036(11) 0.0119(11)
C27 0.0410(14) 0.0338(13) 0.0282(12) -0.0090(11) -0.0067(11) 0.0062(11)
N1 0.0347(11) 0.0239(10) 0.0280(10) -0.0018(8) -0.0051(8) 0.0048(8)
N11 0.0387(11) 0.0215(10) 0.0250(10) -0.0019(8) 0.0016(8) 0.0029(8)
N21 0.0382(11) 0.0252(10) 0.0289(10) -0.0083(8) -0.0032(8) 0.0080(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.8(3)
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 . C1 . 1.247(3) yes
O2 . C7 . 1.206(3) yes
O3 . C7 . 1.311(3) yes
O3 . H31 . 0.846 no
O11 . C11 . 1.250(3) yes
O12 . C17 . 1.205(3) yes
O13 . C17 . 1.306(3) yes
O13 . H131 . 0.816 no
O21 . C21 . 1.241(3) yes
O22 . C27 . 1.203(3) yes
O23 . C27 . 1.305(3) yes
O23 . H231 . 0.835 no
C1 . C2 . 1.508(3) yes
C1 . N1 . 1.335(3) yes
C2 . C3 . 1.524(4) yes
C2 . H21 . 0.964 no
C2 . H22 . 0.968 no
C3 . C4 . 1.520(4) yes
C3 . H32 . 0.973 no
C3 . H264 . 0.975 no
C4 . C5 . 1.528(4) yes
C4 . H41 . 0.966 no
C4 . H42 . 0.972 no
C5 . C6 . 1.537(4) yes
C5 . H51 . 0.984 no
C5 . H52 . 0.974 no
C6 . C7 . 1.522(3) yes
C6 . N1 . 1.463(3) yes
C6 . H61 . 0.982 no
C11 . C12 . 1.500(3) yes
C11 . N11 . 1.335(3) yes
C12 . C13 . 1.540(4) yes
C12 . H121 . 0.969 no
C12 . H122 . 0.979 no
C13 . C14 . 1.526(4) yes
C13 . H132 . 0.976 no
C13 . H262 . 0.976 no
C14 . C15 . 1.524(4) yes
C14 . H141 . 0.964 no
C14 . H142 . 0.982 no
C15 . C16 . 1.541(3) yes
C15 . H151 . 0.978 no
C15 . H152 . 0.971 no
C16 . C17 . 1.520(3) yes
C16 . N11 . 1.456(3) yes
C16 . H161 . 0.984 no
C21 . C22 . 1.509(4) yes
C21 . N21 . 1.338(3) yes
C22 . C23 . 1.521(4) yes
C22 . H221 . 1.007 no
C22 . H222 . 1.008 no
C23 . C24 . 1.531(4) yes
C23 . H232 . 0.985 no
C23 . H263 . 0.992 no
C24 . C25 . 1.535(4) yes
C24 . H241 . 0.999 no
C24 . H242 . 0.983 no
C25 . C26 . 1.500(4) yes
C25 . H251 . 0.994 no
C25 . H252 . 0.993 no
C26 . C27 . 1.529(3) yes
C26 . N21 . 1.454(3) yes
C26 . H261 . 1.007 no
N1 . H11 . 0.850 no
N11 . H111 . 0.854 no
N21 . H211 . 0.849 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
C7 . O3 . H31 . 107.8 no
C17 . O13 . H131 . 107.3 no
C27 . O23 . H231 . 109.0 no
O1 . C1 . C2 . 119.2(2) yes
O1 . C1 . N1 . 121.2(2) yes
C2 . C1 . N1 . 119.6(2) yes
C1 . C2 . C3 . 113.9(2) yes
C1 . C2 . H21 . 107.9 no
C3 . C2 . H21 . 109.8 no
C1 . C2 . H22 . 108.7 no
C3 . C2 . H22 . 108.8 no
H21 . C2 . H22 . 107.5 no
C2 . C3 . C4 . 113.9(2) yes
C2 . C3 . H32 . 107.1 no
C4 . C3 . H32 . 107.8 no
C2 . C3 . H264 . 108.6 no
C4 . C3 . H264 . 109.2 no
H32 . C3 . H264 . 110.1 no
C3 . C4 . C5 . 114.7(2) yes
C3 . C4 . H41 . 108.9 no
C5 . C4 . H41 . 108.9 no
C3 . C4 . H42 . 106.7 no
C5 . C4 . H42 . 107.4 no
H41 . C4 . H42 . 110.2 no
C4 . C5 . C6 . 114.4(2) yes
C4 . C5 . H51 . 109.3 no
C6 . C5 . H51 . 109.1 no
C4 . C5 . H52 . 108.6 no
C6 . C5 . H52 . 107.0 no
H51 . C5 . H52 . 108.2 no
C5 . C6 . C7 . 108.8(2) yes
C5 . C6 . N1 . 113.3(2) yes
C7 . C6 . N1 . 107.30(19) yes
C5 . C6 . H61 . 108.3 no
C7 . C6 . H61 . 108.8 no
N1 . C6 . H61 . 110.3 no
C6 . C7 . O3 . 112.6(2) yes
C6 . C7 . O2 . 122.8(2) yes
O3 . C7 . O2 . 124.5(2) yes
O11 . C11 . C12 . 119.8(2) yes
O11 . C11 . N11 . 121.7(2) yes
C12 . C11 . N11 . 118.4(2) yes
C11 . C12 . C13 . 112.7(2) yes
C11 . C12 . H121 . 107.6 no
C13 . C12 . H121 . 109.6 no
C11 . C12 . H122 . 108.4 no
C13 . C12 . H122 . 109.7 no
H121 . C12 . H122 . 108.8 no
C12 . C13 . C14 . 114.2(2) yes
C12 . C13 . H132 . 107.5 no
C14 . C13 . H132 . 108.4 no
C12 . C13 . H262 . 108.3 no
C14 . C13 . H262 . 108.1 no
H132 . C13 . H262 . 110.4 no
C13 . C14 . C15 . 115.4(2) yes
C13 . C14 . H141 . 109.4 no
C15 . C14 . H141 . 107.8 no
C13 . C14 . H142 . 107.4 no
C15 . C14 . H142 . 108.0 no
H141 . C14 . H142 . 108.7 no
C14 . C15 . C16 . 112.8(2) yes
C14 . C15 . H151 . 109.8 no
C16 . C15 . H151 . 108.4 no
C14 . C15 . H152 . 108.6 no
C16 . C15 . H152 . 109.1 no
H151 . C15 . H152 . 107.9 no
C15 . C16 . C17 . 111.61(19) yes
C15 . C16 . N11 . 112.4(2) yes
C17 . C16 . N11 . 108.06(18) yes
C15 . C16 . H161 . 107.7 no
C17 . C16 . H161 . 106.9 no
N11 . C16 . H161 . 110.0 no
C16 . C17 . O13 . 112.6(2) yes
C16 . C17 . O12 . 122.8(2) yes
O13 . C17 . O12 . 124.6(2) yes
O21 . C21 . C22 . 119.1(2) yes
O21 . C21 . N21 . 122.0(2) yes
C22 . C21 . N21 . 118.9(2) yes
C21 . C22 . C23 . 112.8(2) yes
C21 . C22 . H221 . 111.0 no
C23 . C22 . H221 . 107.2 no
C21 . C22 . H222 . 106.6 no
C23 . C22 . H222 . 110.0 no
H221 . C22 . H222 . 109.1 no
C22 . C23 . C24 . 113.5(3) yes
C22 . C23 . H232 . 102.7 no
C24 . C23 . H232 . 110.6 no
C22 . C23 . H263 . 107.4 no
C24 . C23 . H263 . 108.2 no
H232 . C23 . H263 . 114.4 no
C23 . C24 . C25 . 114.3(2) yes
C23 . C24 . H241 . 104.4 no
C25 . C24 . H241 . 105.8 no
C23 . C24 . H242 . 111.1 no
C25 . C24 . H242 . 110.5 no
H241 . C24 . H242 . 110.5 no
C24 . C25 . C26 . 114.4(2) yes
C24 . C25 . H251 . 107.8 no
C26 . C25 . H251 . 107.6 no
C24 . C25 . H252 . 110.2 no
C26 . C25 . H252 . 107.4 no
H251 . C25 . H252 . 109.2 no
C25 . C26 . C27 . 111.0(2) yes
C25 . C26 . N21 . 113.5(2) yes
C27 . C26 . N21 . 107.47(19) yes
C25 . C26 . H261 . 102.7 no
C27 . C26 . H261 . 109.5 no
N21 . C26 . H261 . 112.7 no
C26 . C27 . O23 . 112.7(2) yes
C26 . C27 . O22 . 122.4(2) yes
O23 . C27 . O22 . 124.9(2) yes
C6 . N1 . C1 . 126.2(2) yes
C6 . N1 . H11 . 116.4 no
C1 . N1 . H11 . 117.2 no
C16 . N11 . C11 . 124.44(19) yes
C16 . N11 . H111 . 118.0 no
C11 . N11 . H111 . 117.5 no
C26 . N21 . C21 . 126.1(2) yes
C26 . N21 . H211 . 116.5 no
C21 . N21 . H211 . 116.9 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
N1 . H11 . O22 . 162.31 0.850 2.253 3.074(4) yes
O3 . H31 . O11 . 169.90 0.846 1.716 2.553(4) yes
N11 . H111 . O2 . 163.85 0.854 2.140 2.970(4) yes
O13 . H131 . O21 . 168.93 0.816 1.750 2.555(4) yes
N21 . H211 . O12 . 162.20 0.849 2.176 2.996(4) yes
O23 . H231 . O1 . 170.44 0.835 1.716 2.543(4) yes
_database_code_depnum_ccdc_archive 'CCDC 1018876'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_3
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6291
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.27304(11)
_cell_length_b                   8.13334(11)
_cell_length_c                   27.2810(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.0045(16)
_cell_angle_gamma                90
_cell_volume                     1391.68(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'

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 0.0181 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 = C13 H21 N1 O5 
# Dc =      1.29 Fooo =    584.00 Mu =      8.26 M =    271.31
# Found Formula = C13 H21 N1 O5 
# Dc =      1.29 FOOO =    584.00 Mu =      8.26 M =    271.31

_chemical_formula_sum            'C13 H21 N1 O5'
_chemical_formula_moiety         'C13 H21 N1 O5'
_chemical_compound_source        .
_chemical_formula_weight         271.31


_cell_measurement_reflns_used    6326
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.826

# Sheldrick geometric approximatio 0.94 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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    'SIR92 (Altomare et al., 1994)'
_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            13198
_reflns_number_total             2770
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections with Friedels Law is 2770 
# Theoretical number of reflections is about 5821 


_diffrn_reflns_theta_min         3.240
_diffrn_reflns_theta_max         76.124
_diffrn_measured_fraction_theta_max 0.956

_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_full 0.980


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              34

_oxford_diffrn_Wilson_B_factor   2.10
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.23
_refine_diff_density_max         0.33


# 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         2766
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0422
_refine_ls_wR_factor_ref         0.0899
_refine_ls_goodness_of_fit_ref   0.9877
_refine_ls_shift/su_max          0.0006295
_refine_ls_shift/su_mean         0.0001051


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2767
_refine_ls_R_factor_all          0.0422
_refine_ls_wR_factor_all         0.0901

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2364
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_gt          0.0854

# 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 .


_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) + ( 0.04P)² + 0.45P] 
 ,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 0.08030(19) 0.35192(12) 0.65973(4) 0.0422 1.0000 Uani . . . . . .
O2 O 0.44827(15) 0.19416(12) 0.48869(3) 0.0319 1.0000 Uani . . . . . .
O3 O 0.12545(13) 0.18214(10) 0.52262(3) 0.0242 1.0000 Uani . . . . . .
O4 O 0.25726(16) -0.11196(10) 0.62124(3) 0.0311 1.0000 Uani . . . . . .
O5 O 0.08447(16) 0.04655(10) 0.67492(3) 0.0313 1.0000 Uani . . . . . .
C1 C 0.2048(2) 0.32716(14) 0.62746(4) 0.0221 1.0000 Uani . . . . . .
C2 C 0.2901(2) 0.47029(14) 0.59815(5) 0.0249 1.0000 Uani . . . . . .
C3 C 0.5280(2) 0.50680(16) 0.60614(5) 0.0332 1.0000 Uani . . . . . .
C4 C 0.6709(2) 0.40230(17) 0.57466(5) 0.0329 1.0000 Uani . . . . . .
C5 C 0.6508(2) 0.21818(16) 0.58399(5) 0.0284 1.0000 Uani . . . . . .
C6 C 0.42916(19) 0.14241(14) 0.57510(4) 0.0208 1.0000 Uani . . . . . .
C7 C 0.3386(2) 0.17834(13) 0.52415(4) 0.0215 1.0000 Uani . . . . . .
C8 C 0.0310(2) 0.20956(17) 0.47440(5) 0.0309 1.0000 Uani . . . . . .
C9 C 0.20674(18) 0.02058(14) 0.63716(4) 0.0193 1.0000 Uani . . . . . .
C10 C -0.0120(2) -0.09451(15) 0.70127(5) 0.0268 1.0000 Uani . . . . . .
C11 C -0.1399(3) -0.0064(2) 0.73986(6) 0.0540 1.0000 Uani . . . . . .
C12 C 0.1609(3) -0.2007(2) 0.72431(6) 0.0461 1.0000 Uani . . . . . .
C13 C -0.1567(2) -0.18991(17) 0.66669(5) 0.0331 1.0000 Uani . . . . . .
N1 N 0.27785(16) 0.16810(11) 0.61508(3) 0.0191 1.0000 Uani . . . . . .
H21 H 0.2612 0.4534 0.5628 0.0285 1.0000 Uiso R . . . . .
H22 H 0.2060 0.5639 0.6093 0.0307 1.0000 Uiso R . . . . .
H31 H 0.5647 0.4879 0.6402 0.0413 1.0000 Uiso R . . . . .
H32 H 0.5493 0.6217 0.5994 0.0411 1.0000 Uiso R . . . . .
H41 H 0.8221 0.4318 0.5806 0.0401 1.0000 Uiso R . . . . .
H42 H 0.6381 0.4236 0.5402 0.0361 1.0000 Uiso R . . . . .
H51 H 0.6872 0.1950 0.6185 0.0334 1.0000 Uiso R . . . . .
H52 H 0.7457 0.1566 0.5622 0.0328 1.0000 Uiso R . . . . .
H61 H 0.4493 0.0273 0.5736 0.0243 1.0000 Uiso R . . . . .
H81 H -0.1230 0.2082 0.4780 0.0466 1.0000 Uiso R . . . . .
H82 H 0.0739 0.1212 0.4525 0.0462 1.0000 Uiso R . . . . .
H83 H 0.0772 0.3156 0.4626 0.0455 1.0000 Uiso R . . . . .
H111 H -0.2470 0.0628 0.7232 0.0808 1.0000 Uiso R . . . . .
H112 H -0.0490 0.0652 0.7600 0.0798 1.0000 Uiso R . . . . .
H113 H -0.2110 -0.0878 0.7599 0.0785 1.0000 Uiso R . . . . .
H121 H 0.2438 -0.2571 0.6995 0.0676 1.0000 Uiso R . . . . .
H122 H 0.2530 -0.1304 0.7440 0.0702 1.0000 Uiso R . . . . .
H123 H 0.0937 -0.2797 0.7461 0.0675 1.0000 Uiso R . . . . .
H131 H -0.0785 -0.2486 0.6424 0.0500 1.0000 Uiso R . . . . .
H132 H -0.2563 -0.1125 0.6502 0.0510 1.0000 Uiso R . . . . .
H133 H -0.2418 -0.2709 0.6850 0.0515 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0604(7) 0.0279(5) 0.0391(6) 0.0028(4) 0.0237(5) 0.0121(5)
O2 0.0303(5) 0.0405(5) 0.0252(5) 0.0050(4) 0.0103(4) 0.0011(4)
O3 0.0221(4) 0.0304(5) 0.0201(4) 0.0014(3) 0.0004(3) -0.0039(3)
O4 0.0403(6) 0.0187(4) 0.0348(5) 0.0014(4) 0.0154(4) 0.0003(4)
O5 0.0442(6) 0.0207(4) 0.0295(5) -0.0023(4) 0.0187(4) -0.0081(4)
C1 0.0250(6) 0.0202(5) 0.0211(6) -0.0015(4) -0.0014(5) 0.0012(4)
C2 0.0299(7) 0.0176(5) 0.0270(6) 0.0003(5) -0.0021(5) -0.0002(5)
C3 0.0356(7) 0.0260(6) 0.0377(8) 0.0028(6) -0.0097(6) -0.0113(5)
C4 0.0206(6) 0.0335(7) 0.0442(8) 0.0123(6) -0.0049(6) -0.0086(5)
C5 0.0184(6) 0.0316(6) 0.0354(7) 0.0100(5) 0.0008(5) 0.0003(5)
C6 0.0200(6) 0.0199(5) 0.0227(6) 0.0024(4) 0.0047(5) 0.0015(4)
C7 0.0237(6) 0.0181(5) 0.0227(6) 0.0004(4) 0.0045(5) -0.0009(4)
C8 0.0320(7) 0.0364(7) 0.0240(7) 0.0056(5) -0.0047(6) -0.0055(6)
C9 0.0198(6) 0.0197(5) 0.0186(6) 0.0006(4) 0.0002(4) -0.0024(4)
C10 0.0349(7) 0.0243(6) 0.0215(6) 0.0010(5) 0.0094(5) -0.0091(5)
C11 0.0783(13) 0.0398(8) 0.0453(10) -0.0107(7) 0.0387(9) -0.0181(8)
C12 0.0444(9) 0.0591(10) 0.0345(8) 0.0205(7) -0.0072(7) -0.0107(8)
C13 0.0316(7) 0.0378(7) 0.0299(7) 0.0027(6) 0.0025(6) -0.0117(6)
N1 0.0202(5) 0.0178(5) 0.0195(5) 0.0004(4) 0.0030(4) -0.0010(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.37(14)
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 . C1 . 1.2039(16) yes
O2 . C7 . 1.2037(15) yes
O3 . C7 . 1.3376(15) yes
O3 . C8 . 1.4506(14) yes
O4 . C9 . 1.2066(14) yes
O5 . C9 . 1.3121(15) yes
O5 . C10 . 1.4882(14) yes
C1 . C2 . 1.5154(17) yes
C1 . N1 . 1.4154(15) yes
C2 . C3 . 1.5334(18) yes
C2 . H21 . 0.987 no
C2 . H22 . 0.977 no
C3 . C4 . 1.514(2) yes
C3 . H31 . 0.966 no
C3 . H32 . 0.962 no
C4 . C5 . 1.5246(18) yes
C4 . H41 . 0.989 no
C4 . H42 . 0.975 no
C5 . C6 . 1.5364(17) yes
C5 . H51 . 0.984 no
C5 . H52 . 0.985 no
C6 . C7 . 1.5206(16) yes
C6 . N1 . 1.4733(15) yes
C6 . H61 . 0.945 no
C8 . H81 . 0.973 no
C8 . H82 . 0.976 no
C8 . H83 . 0.967 no
C9 . N1 . 1.4181(14) yes
C10 . C11 . 1.515(2) yes
C10 . C12 . 1.514(2) yes
C10 . C13 . 1.5120(18) yes
C11 . H111 . 0.982 no
C11 . H112 . 0.978 no
C11 . H113 . 0.972 no
C12 . H121 . 0.975 no
C12 . H122 . 0.969 no
C12 . H123 . 0.976 no
C13 . H131 . 0.959 no
C13 . H132 . 0.989 no
C13 . H133 . 0.988 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
C7 . O3 . C8 . 115.09(10) yes
C9 . O5 . C10 . 120.23(9) yes
O1 . C1 . C2 . 119.81(11) yes
O1 . C1 . N1 . 122.99(11) yes
C2 . C1 . N1 . 117.21(11) yes
C1 . C2 . C3 . 115.20(10) yes
C1 . C2 . H21 . 110.3 no
C3 . C2 . H21 . 109.1 no
C1 . C2 . H22 . 103.7 no
C3 . C2 . H22 . 109.5 no
H21 . C2 . H22 . 108.7 no
C2 . C3 . C4 . 113.28(11) yes
C2 . C3 . H31 . 108.7 no
C4 . C3 . H31 . 108.9 no
C2 . C3 . H32 . 107.4 no
C4 . C3 . H32 . 110.6 no
H31 . C3 . H32 . 107.8 no
C3 . C4 . C5 . 113.90(11) yes
C3 . C4 . H41 . 110.3 no
C5 . C4 . H41 . 107.0 no
C3 . C4 . H42 . 109.3 no
C5 . C4 . H42 . 108.6 no
H41 . C4 . H42 . 107.5 no
C4 . C5 . C6 . 116.42(10) yes
C4 . C5 . H51 . 109.2 no
C6 . C5 . H51 . 105.6 no
C4 . C5 . H52 . 110.2 no
C6 . C5 . H52 . 104.8 no
H51 . C5 . H52 . 110.4 no
C5 . C6 . C7 . 112.94(10) yes
C5 . C6 . N1 . 114.79(10) yes
C7 . C6 . N1 . 114.48(10) yes
C5 . C6 . H61 . 106.4 no
C7 . C6 . H61 . 101.4 no
N1 . C6 . H61 . 105.2 no
C6 . C7 . O3 . 112.96(10) yes
C6 . C7 . O2 . 123.07(11) yes
O3 . C7 . O2 . 123.88(11) yes
O3 . C8 . H81 . 107.3 no
O3 . C8 . H82 . 109.3 no
H81 . C8 . H82 . 109.8 no
O3 . C8 . H83 . 108.6 no
H81 . C8 . H83 . 110.3 no
H82 . C8 . H83 . 111.4 no
O5 . C9 . O4 . 125.96(11) yes
O5 . C9 . N1 . 112.95(10) yes
O4 . C9 . N1 . 121.09(11) yes
O5 . C10 . C11 . 101.30(10) yes
O5 . C10 . C12 . 110.23(11) yes
C11 . C10 . C12 . 111.43(14) yes
O5 . C10 . C13 . 109.81(10) yes
C11 . C10 . C13 . 110.91(13) yes
C12 . C10 . C13 . 112.59(12) yes
C10 . C11 . H111 . 108.4 no
C10 . C11 . H112 . 111.2 no
H111 . C11 . H112 . 107.9 no
C10 . C11 . H113 . 108.8 no
H111 . C11 . H113 . 109.5 no
H112 . C11 . H113 . 110.9 no
C10 . C12 . H121 . 111.5 no
C10 . C12 . H122 . 108.0 no
H121 . C12 . H122 . 110.0 no
C10 . C12 . H123 . 108.3 no
H121 . C12 . H123 . 110.7 no
H122 . C12 . H123 . 108.1 no
C10 . C13 . H131 . 112.2 no
C10 . C13 . H132 . 108.9 no
H131 . C13 . H132 . 109.3 no
C10 . C13 . H133 . 110.5 no
H131 . C13 . H133 . 107.7 no
H132 . C13 . H133 . 108.1 no
C6 . N1 . C9 . 113.96(9) yes
C6 . N1 . C1 . 121.47(9) yes
C9 . N1 . C1 . 124.49(10) yes
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 . O2 2_656 139.43 0.945 2.565 3.3406(19) yes
_database_code_depnum_ccdc_archive 'CCDC 1018877'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5-cis
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6288
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.54965(8)
_cell_length_b                   7.8511(1)
_cell_length_c                   23.3724(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.6507(11)
_cell_angle_gamma                90
_cell_volume                     1378.62(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_symmetry_space_group_name_Hall  '-P 2ybc'

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 0.0181 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'
S 0.3331 0.5567 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 = C11 H18 N2 O3 S2 
# Dc =      1.40 Fooo =    616.00 Mu =     35.39 M =    290.41
# Found Formula = C11 H18 N2 O3 S2 
# Dc =      1.40 FOOO =    616.00 Mu =     35.39 M =    290.41

_chemical_formula_sum            'C11 H18 N2 O3 S2'
_chemical_formula_moiety         'C11 H18 N2 O3 S2'
_chemical_compound_source        .
_chemical_formula_weight         290.41


_cell_measurement_reflns_used    7672
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    3.539

# Sheldrick geometric approximatio 0.51 0.78 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_T_max  0.78
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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    'SIR92 (Altomare et al., 1994)'
_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            11617
_reflns_number_total             2866
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections with Friedels Law is 2866 
# Theoretical number of reflections is about 5781 


_diffrn_reflns_theta_min         3.801
_diffrn_reflns_theta_max         76.330
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        74.803
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   2.01
_oxford_diffrn_Wilson_scale      0.03

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.30


# 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         2866
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0297
_refine_ls_wR_factor_ref         0.0742
_refine_ls_goodness_of_fit_ref   0.9588
_refine_ls_shift/su_max          0.0013764
_refine_ls_shift/su_mean         0.0001511


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2866
_refine_ls_R_factor_all          0.0297
_refine_ls_wR_factor_all         0.0742

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2668
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_gt          0.0718

# 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 .


_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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.173E+04 0.291E+04 0.184E+04 794. 202. 
;

# 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
C1 C 1.02062(16) -0.01037(15) 0.75453(5) 0.0198 1.0000 Uani . . . . . .
C2 C 0.92338(15) 0.03818(15) 0.69652(5) 0.0195 1.0000 Uani . . . . . .
C3 C 0.76990(16) -0.08593(17) 0.67864(5) 0.0241 1.0000 Uani . . . . . .
C4 C 0.60023(16) -0.03834(18) 0.70558(6) 0.0276 1.0000 Uani . . . . . .
C5 C 0.61028(17) -0.05914(18) 0.77061(6) 0.0274 1.0000 Uani . . . . . .
C6 C 0.74709(15) 0.05901(16) 0.80356(5) 0.0217 1.0000 Uani . . . . . .
C7 C 0.71487(17) 0.06092(16) 0.86657(5) 0.0235 1.0000 Uani . . . . . .
C8 C 0.5048(2) 0.1270(2) 0.93140(6) 0.0391 1.0000 Uani . . . . . .
C9 C 0.99799(17) 0.14797(16) 0.58690(5) 0.0230 1.0000 Uani . . . . . .
C10 C 1.0534(2) 0.25322(18) 0.49183(6) 0.0329 1.0000 Uani . . . . . .
C11 C 1.2864(2) 0.0906(2) 0.54948(7) 0.0381 1.0000 Uani . . . . . .
S1 S 1.09726(4) 0.03592(4) 0.647817(12) 0.0232 1.0000 Uani . . . . . .
S2 S 0.79596(4) 0.23717(5) 0.584065(14) 0.0308 1.0000 Uani . . . . . .
N1 N 0.93106(13) 0.00386(14) 0.80117(4) 0.0217 1.0000 Uani . . . . . .
N2 N 1.10361(15) 0.15502(15) 0.54422(5) 0.0268 1.0000 Uani . . . . . .
O1 O 1.17392(11) -0.06529(13) 0.75819(4) 0.0265 1.0000 Uani . . . . . .
O2 O 0.81211(14) 0.00141(16) 0.90485(4) 0.0373 1.0000 Uani . . . . . .
O3 O 0.55968(13) 0.13393(15) 0.87403(4) 0.0375 1.0000 Uani . . . . . .
H11 H 0.9768 -0.0377 0.8339 0.0223 1.0000 Uiso R . . . . .
H21 H 0.8700 0.1507 0.6955 0.0200 1.0000 Uiso R . . . . .
H31 H 0.7991 -0.1984 0.6905 0.0261 1.0000 Uiso R . . . . .
H32 H 0.7390 -0.0883 0.6379 0.0291 1.0000 Uiso R . . . . .
H41 H 0.5675 0.0824 0.6954 0.0332 1.0000 Uiso R . . . . .
H42 H 0.5059 -0.1078 0.6872 0.0311 1.0000 Uiso R . . . . .
H51 H 0.6403 -0.1793 0.7819 0.0297 1.0000 Uiso R . . . . .
H52 H 0.4937 -0.0308 0.7831 0.0317 1.0000 Uiso R . . . . .
H61 H 0.7244 0.1710 0.7898 0.0218 1.0000 Uiso R . . . . .
H81 H 0.3999 0.2007 0.9313 0.0576 1.0000 Uiso R . . . . .
H82 H 0.5955 0.1718 0.9604 0.0551 1.0000 Uiso R . . . . .
H83 H 0.4729 0.0147 0.9408 0.0590 1.0000 Uiso R . . . . .
H101 H 1.1188 0.3589 0.4945 0.0484 1.0000 Uiso R . . . . .
H102 H 0.9278 0.2728 0.4897 0.0471 1.0000 Uiso R . . . . .
H103 H 1.0891 0.1872 0.4597 0.0475 1.0000 Uiso R . . . . .
H111 H 1.2883 -0.0049 0.5734 0.0577 1.0000 Uiso R . . . . .
H112 H 1.3258 0.0547 0.5143 0.0567 1.0000 Uiso R . . . . .
H113 H 1.3602 0.1780 0.5693 0.0571 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0165(5) 0.0205(6) 0.0224(6) -0.0006(4) 0.0021(4) -0.0024(4)
C2 0.0159(5) 0.0226(6) 0.0202(5) -0.0001(4) 0.0033(4) -0.0001(4)
C3 0.0195(6) 0.0272(6) 0.0253(6) -0.0041(5) 0.0008(4) -0.0025(5)
C4 0.0157(6) 0.0381(8) 0.0286(7) -0.0034(5) 0.0001(5) -0.0036(5)
C5 0.0163(5) 0.0358(7) 0.0305(7) -0.0003(5) 0.0045(5) -0.0041(5)
C6 0.0155(5) 0.0270(6) 0.0233(6) 0.0021(5) 0.0045(4) 0.0016(5)
C7 0.0220(6) 0.0243(6) 0.0250(6) 0.0019(5) 0.0058(5) 0.0000(5)
C8 0.0353(8) 0.0556(10) 0.0295(7) 0.0046(7) 0.0180(6) 0.0044(7)
C9 0.0238(6) 0.0236(6) 0.0217(6) -0.0022(5) 0.0021(4) -0.0011(5)
C10 0.0398(8) 0.0370(8) 0.0222(6) 0.0036(5) 0.0049(5) -0.0036(6)
C11 0.0310(7) 0.0487(9) 0.0368(8) 0.0048(7) 0.0148(6) 0.0076(7)
S1 0.01765(16) 0.03018(18) 0.02217(16) 0.00161(11) 0.00421(12) 0.00327(11)
S2 0.02353(17) 0.0412(2) 0.02746(18) 0.00504(13) 0.00138(13) 0.00769(13)
N1 0.0152(5) 0.0296(5) 0.0203(5) 0.0029(4) 0.0018(4) 0.0019(4)
N2 0.0276(5) 0.0300(6) 0.0236(5) 0.0008(4) 0.0064(4) 0.0010(5)
O1 0.0161(4) 0.0356(5) 0.0281(5) 0.0028(4) 0.0026(3) 0.0037(4)
O2 0.0375(6) 0.0517(6) 0.0227(5) 0.0022(4) 0.0025(4) 0.0163(5)
O3 0.0293(5) 0.0582(7) 0.0272(5) 0.0104(4) 0.0140(4) 0.0160(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.19(10)
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
C1 . C2 . 1.5253(16) yes
C1 . N1 . 1.3429(16) yes
C1 . O1 . 1.2301(15) yes
C2 . C3 . 1.5399(16) yes
C2 . S1 . 1.8203(12) yes
C2 . H21 . 0.970 no
C3 . C4 . 1.5283(17) yes
C3 . H31 . 0.945 no
C3 . H32 . 0.959 no
C4 . C5 . 1.5231(18) yes
C4 . H41 . 1.003 no
C4 . H42 . 0.964 no
C5 . C6 . 1.5374(17) yes
C5 . H51 . 1.000 no
C5 . H52 . 0.980 no
C6 . C7 . 1.5163(17) yes
C6 . N1 . 1.4611(14) yes
C6 . H61 . 0.946 no
C7 . O2 . 1.1951(16) yes
C7 . O3 . 1.3311(16) yes
C8 . O3 . 1.4427(15) yes
C8 . H81 . 0.981 no
C8 . H82 . 0.980 no
C8 . H83 . 0.945 no
C9 . S1 . 1.7755(13) yes
C9 . S2 . 1.6737(13) yes
C9 . N2 . 1.3383(16) yes
C10 . N2 . 1.4648(17) yes
C10 . H101 . 0.964 no
C10 . H102 . 0.957 no
C10 . H103 . 0.972 no
C11 . N2 . 1.4636(18) yes
C11 . H111 . 0.935 no
C11 . H112 . 0.944 no
C11 . H113 . 0.972 no
N1 . H11 . 0.872 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 . C1 . N1 . 117.65(10) yes
C2 . C1 . O1 . 121.10(11) yes
N1 . C1 . O1 . 121.21(11) yes
C1 . C2 . C3 . 111.50(10) yes
C1 . C2 . S1 . 103.88(8) yes
C3 . C2 . S1 . 113.20(8) yes
C1 . C2 . H21 . 114.3 no
C3 . C2 . H21 . 105.6 no
S1 . C2 . H21 . 108.4 no
C2 . C3 . C4 . 111.86(10) yes
C2 . C3 . H31 . 111.4 no
C4 . C3 . H31 . 106.8 no
C2 . C3 . H32 . 112.6 no
C4 . C3 . H32 . 106.4 no
H31 . C3 . H32 . 107.5 no
C3 . C4 . C5 . 115.06(11) yes
C3 . C4 . H41 . 109.3 no
C5 . C4 . H41 . 109.0 no
C3 . C4 . H42 . 106.9 no
C5 . C4 . H42 . 110.2 no
H41 . C4 . H42 . 106.0 no
C4 . C5 . C6 . 113.58(11) yes
C4 . C5 . H51 . 110.7 no
C6 . C5 . H51 . 108.3 no
C4 . C5 . H52 . 108.4 no
C6 . C5 . H52 . 107.0 no
H51 . C5 . H52 . 108.8 no
C5 . C6 . C7 . 109.17(10) yes
C5 . C6 . N1 . 113.35(10) yes
C7 . C6 . N1 . 106.50(10) yes
C5 . C6 . H61 . 107.5 no
C7 . C6 . H61 . 106.3 no
N1 . C6 . H61 . 113.8 no
C6 . C7 . O2 . 125.29(12) yes
C6 . C7 . O3 . 111.03(10) yes
O2 . C7 . O3 . 123.65(12) yes
O3 . C8 . H81 . 106.4 no
O3 . C8 . H82 . 112.7 no
H81 . C8 . H82 . 107.4 no
O3 . C8 . H83 . 110.8 no
H81 . C8 . H83 . 109.0 no
H82 . C8 . H83 . 110.5 no
S1 . C9 . S2 . 123.38(7) yes
S1 . C9 . N2 . 112.51(9) yes
S2 . C9 . N2 . 124.11(10) yes
N2 . C10 . H101 . 108.1 no
N2 . C10 . H102 . 107.6 no
H101 . C10 . H102 . 111.3 no
N2 . C10 . H103 . 107.2 no
H101 . C10 . H103 . 109.3 no
H102 . C10 . H103 . 113.1 no
N2 . C11 . H111 . 106.6 no
N2 . C11 . H112 . 113.9 no
H111 . C11 . H112 . 107.1 no
N2 . C11 . H113 . 106.7 no
H111 . C11 . H113 . 107.9 no
H112 . C11 . H113 . 114.2 no
C2 . S1 . C9 . 102.89(6) yes
C6 . N1 . C1 . 127.75(10) yes
C6 . N1 . H11 . 111.9 no
C1 . N1 . H11 . 119.6 no
C10 . N2 . C11 . 114.60(11) yes
C10 . N2 . C9 . 121.39(11) yes
C11 . N2 . C9 . 123.31(11) yes
C8 . O3 . C7 . 116.25(11) yes
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
C2 . H21 . O1 3_756 150.27 0.970 2.515 3.3920(19) yes
C4 . H42 . O3 3_646 143.99 0.964 2.503 3.3314(19) yes
C5 . H52 . O1 1_455 143.03 0.980 2.442 3.2789(19) yes
C6 . H61 . O1 3_756 149.89 0.946 2.510 3.3628(19) yes
_database_code_depnum_ccdc_archive 'CCDC 1018878'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_5-trans
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6316
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.9432(6)
_cell_length_b                   8.4258(6)
_cell_length_c                   11.2990(8)
_cell_angle_alpha                89.703(6)
_cell_angle_beta                 71.855(6)
_cell_angle_gamma                73.959(6)
_cell_volume                     687.92(9)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-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 = C11 H18 N2 O3 S2 
# Dc =      1.40 Fooo =    308.00 Mu =      3.89 M =    290.41
# Found Formula = C11 H18 N2 O3 S2 
# Dc =      1.40 FOOO =    308.00 Mu =      3.89 M =    290.41

_chemical_formula_sum            'C11 H18 N2 O3 S2'
_chemical_formula_moiety         'C11 H18 N2 O3 S2'
_chemical_compound_source        .
_chemical_formula_weight         290.41


_cell_measurement_reflns_used    1932
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.04
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.21

_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.389

# Sheldrick geometric approximatio 0.93 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_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       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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            6132
_reflns_number_total             3550
_diffrn_reflns_av_R_equivalents  0.037
# Number of reflections with Friedels Law is 3550 
# Theoretical number of reflections is about 8551 


_diffrn_reflns_theta_min         3.025
_diffrn_reflns_theta_max         30.707
_diffrn_measured_fraction_theta_max 0.830

_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -10
_reflns_limit_h_max              11
_reflns_limit_k_min              -11
_reflns_limit_k_max              11
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   1.87
_oxford_diffrn_Wilson_scale      0.02

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

_refine_diff_density_min         -0.76
_refine_diff_density_max         0.66


# 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         3544
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0874
_refine_ls_wR_factor_ref         0.1155
_refine_ls_goodness_of_fit_ref   1.0097
_refine_ls_shift/su_max          0.0004307
_refine_ls_shift/su_mean         0.0000485


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3547
_refine_ls_R_factor_all          0.0878
_refine_ls_wR_factor_all         0.1161

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2530
_refine_ls_R_factor_gt           0.0565
_refine_ls_wR_factor_gt          0.0953

# 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 .


_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) + ( 0.02P)² + 0.68P] 
 ,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
C1 C 0.5436(4) 0.3942(3) 0.8233(2) 0.0236 1.0000 Uani . . . . . .
C2 C 0.5606(3) 0.3275(3) 0.6948(2) 0.0216 1.0000 Uani . . . . . .
C3 C 0.3922(4) 0.4170(3) 0.6554(3) 0.0245 1.0000 Uani . . . . . .
C4 C 0.2315(4) 0.3427(3) 0.7063(3) 0.0268 1.0000 Uani . . . . . .
C5 C 0.1392(4) 0.3666(3) 0.8467(3) 0.0266 1.0000 Uani . . . . . .
C6 C 0.2642(4) 0.2926(3) 0.9253(3) 0.0247 1.0000 Uani . . . . . .
C7 C 0.3485(4) 0.1053(3) 0.9000(2) 0.0246 1.0000 Uani . . . . . .
C8 C 0.2783(4) -0.1488(4) 0.9160(3) 0.0419 1.0000 Uani . . . . . .
C9 C 0.8248(4) 0.1953(3) 0.4641(2) 0.0232 1.0000 Uani . . . . . .
C10 C 1.0455(4) 0.0605(4) 0.2657(3) 0.0340 1.0000 Uani . . . . . .
C11 C 1.1203(4) 0.2659(4) 0.3818(3) 0.0342 1.0000 Uani . . . . . .
S1 S 0.77991(9) 0.34428(9) 0.59009(6) 0.0255 1.0000 Uani . . . . . .
S2 S 0.67820(10) 0.09019(9) 0.45800(7) 0.0320 1.0000 Uani . . . . . .
O1 O 0.6498(3) 0.4692(2) 0.83911(18) 0.0326 1.0000 Uani . . . . . .
O2 O 0.5105(3) 0.0336(2) 0.8640(2) 0.0335 1.0000 Uani . . . . . .
O3 O 0.2147(3) 0.0313(2) 0.92794(19) 0.0304 1.0000 Uani . . . . . .
N1 N 0.4022(3) 0.3780(3) 0.9209(2) 0.0260 1.0000 Uani . . . . . .
N2 N 0.9874(3) 0.1782(3) 0.3752(2) 0.0258 1.0000 Uani . . . . . .
H11 H 0.3919 0.4260 0.9920 0.0317 1.0000 Uiso R . . . . .
H21 H 0.5689 0.2103 0.6951 0.0251 1.0000 Uiso R . . . . .
H31 H 0.3538 0.5331 0.6823 0.0291 1.0000 Uiso R . . . . .
H32 H 0.4297 0.4047 0.5652 0.0288 1.0000 Uiso R . . . . .
H41 H 0.1374 0.3928 0.6681 0.0320 1.0000 Uiso R . . . . .
H42 H 0.2768 0.2250 0.6797 0.0319 1.0000 Uiso R . . . . .
H51 H 0.0890 0.4851 0.8733 0.0318 1.0000 Uiso R . . . . .
H52 H 0.0376 0.3194 0.8680 0.0318 1.0000 Uiso R . . . . .
H61 H 0.1850 0.3084 1.0118 0.0292 1.0000 Uiso R . . . . .
H81 H 0.3490 -0.1873 0.8302 0.0625 1.0000 Uiso R . . . . .
H82 H 0.3524 -0.1866 0.9694 0.0629 1.0000 Uiso R . . . . .
H83 H 0.1700 -0.1871 0.9411 0.0625 1.0000 Uiso R . . . . .
H101 H 1.1574 0.0691 0.2082 0.0521 1.0000 Uiso R . . . . .
H102 H 0.9535 0.0792 0.2259 0.0524 1.0000 Uiso R . . . . .
H103 H 1.0653 -0.0487 0.2908 0.0524 1.0000 Uiso R . . . . .
H111 H 1.1646 0.2341 0.4490 0.0523 1.0000 Uiso R . . . . .
H112 H 1.2211 0.2402 0.3077 0.0528 1.0000 Uiso R . . . . .
H113 H 1.0658 0.3827 0.3936 0.0530 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0253(13) 0.0252(13) 0.0184(14) -0.0013(11) -0.0057(12) -0.0059(11)
C2 0.0239(13) 0.0253(13) 0.0154(13) -0.0019(11) -0.0029(11) -0.0109(11)
C3 0.0307(14) 0.0229(13) 0.0194(14) 0.0008(11) -0.0091(12) -0.0061(11)
C4 0.0240(14) 0.0278(14) 0.0282(16) -0.0001(12) -0.0112(13) -0.0037(12)
C5 0.0213(13) 0.0264(14) 0.0293(16) 0.0002(12) -0.0074(12) -0.0034(11)
C6 0.0227(13) 0.0317(14) 0.0163(13) -0.0037(11) -0.0012(11) -0.0082(12)
C7 0.0264(14) 0.0327(15) 0.0159(13) 0.0031(11) -0.0068(12) -0.0108(12)
C8 0.0435(18) 0.0280(16) 0.062(2) 0.0107(16) -0.0242(18) -0.0140(14)
C9 0.0261(13) 0.0232(13) 0.0199(14) 0.0002(11) -0.0072(12) -0.0068(11)
C10 0.0266(15) 0.0414(17) 0.0246(16) -0.0081(13) 0.0006(13) -0.0051(13)
C11 0.0268(14) 0.0416(17) 0.0335(17) 0.0018(14) -0.0035(13) -0.0157(13)
S1 0.0290(4) 0.0292(4) 0.0203(4) -0.0021(3) -0.0044(3) -0.0157(3)
S2 0.0305(4) 0.0334(4) 0.0306(4) -0.0106(3) -0.0011(3) -0.0163(3)
O1 0.0370(11) 0.0409(12) 0.0248(11) -0.0049(9) -0.0085(9) -0.0208(10)
O2 0.0226(10) 0.0331(11) 0.0384(13) 0.0083(9) -0.0044(10) -0.0043(9)
O3 0.0266(10) 0.0302(11) 0.0362(12) 0.0046(9) -0.0106(9) -0.0106(9)
N1 0.0307(12) 0.0321(13) 0.0162(12) -0.0053(10) -0.0057(10) -0.0127(10)
N2 0.0217(11) 0.0321(13) 0.0210(12) 0.0001(10) -0.0017(10) -0.0097(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          7.48(19)
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
C1 . C2 . 1.512(3) yes
C1 . O1 . 1.238(3) yes
C1 . N1 . 1.345(3) yes
C2 . C3 . 1.538(3) yes
C2 . S1 . 1.818(3) yes
C2 . H21 . 0.971 no
C3 . C4 . 1.527(4) yes
C3 . H31 . 0.961 no
C3 . H32 . 0.965 no
C4 . C5 . 1.514(4) yes
C4 . H41 . 0.973 no
C4 . H42 . 0.971 no
C5 . C6 . 1.537(4) yes
C5 . H51 . 0.977 no
C5 . H52 . 0.960 no
C6 . C7 . 1.524(4) yes
C6 . N1 . 1.457(3) yes
C6 . H61 . 0.970 no
C7 . O2 . 1.197(3) yes
C7 . O3 . 1.332(3) yes
C8 . O3 . 1.453(3) yes
C8 . H81 . 0.961 no
C8 . H82 . 0.963 no
C8 . H83 . 0.962 no
C9 . S1 . 1.784(3) yes
C9 . S2 . 1.663(3) yes
C9 . N2 . 1.338(3) yes
C10 . N2 . 1.460(3) yes
C10 . H101 . 0.945 no
C10 . H102 . 0.949 no
C10 . H103 . 0.947 no
C11 . N2 . 1.466(3) yes
C11 . H111 . 0.941 no
C11 . H112 . 0.937 no
C11 . H113 . 0.951 no
N1 . H11 . 0.871 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 . C1 . O1 . 121.8(2) yes
C2 . C1 . N1 . 118.1(2) yes
O1 . C1 . N1 . 120.0(2) yes
C1 . C2 . C3 . 111.7(2) yes
C1 . C2 . S1 . 106.34(17) yes
C3 . C2 . S1 . 114.05(19) yes
C1 . C2 . H21 . 109.5 no
C3 . C2 . H21 . 108.1 no
S1 . C2 . H21 . 107.1 no
C2 . C3 . C4 . 112.1(2) yes
C2 . C3 . H31 . 109.8 no
C4 . C3 . H31 . 110.5 no
C2 . C3 . H32 . 107.9 no
C4 . C3 . H32 . 108.0 no
H31 . C3 . H32 . 108.4 no
C3 . C4 . C5 . 116.0(2) yes
C3 . C4 . H41 . 108.1 no
C5 . C4 . H41 . 107.6 no
C3 . C4 . H42 . 108.0 no
C5 . C4 . H42 . 109.1 no
H41 . C4 . H42 . 107.7 no
C4 . C5 . C6 . 116.0(2) yes
C4 . C5 . H51 . 109.3 no
C6 . C5 . H51 . 106.3 no
C4 . C5 . H52 . 109.0 no
C6 . C5 . H52 . 108.2 no
H51 . C5 . H52 . 107.8 no
C5 . C6 . C7 . 113.6(2) yes
C5 . C6 . N1 . 113.6(2) yes
C7 . C6 . N1 . 112.2(2) yes
C5 . C6 . H61 . 106.8 no
C7 . C6 . H61 . 104.1 no
N1 . C6 . H61 . 105.6 no
C6 . C7 . O2 . 125.7(3) yes
C6 . C7 . O3 . 109.8(2) yes
O2 . C7 . O3 . 124.5(3) yes
O3 . C8 . H81 . 109.2 no
O3 . C8 . H82 . 109.8 no
H81 . C8 . H82 . 110.6 no
O3 . C8 . H83 . 107.1 no
H81 . C8 . H83 . 109.9 no
H82 . C8 . H83 . 110.2 no
S1 . C9 . S2 . 123.27(16) yes
S1 . C9 . N2 . 113.00(19) yes
S2 . C9 . N2 . 123.7(2) yes
N2 . C10 . H101 . 110.1 no
N2 . C10 . H102 . 111.2 no
H101 . C10 . H102 . 109.6 no
N2 . C10 . H103 . 109.3 no
H101 . C10 . H103 . 108.5 no
H102 . C10 . H103 . 108.1 no
N2 . C11 . H111 . 110.5 no
N2 . C11 . H112 . 109.7 no
H111 . C11 . H112 . 108.5 no
N2 . C11 . H113 . 111.6 no
H111 . C11 . H113 . 107.6 no
H112 . C11 . H113 . 108.8 no
C2 . S1 . C9 . 101.37(12) yes
C8 . O3 . C7 . 114.9(2) yes
C6 . N1 . C1 . 129.6(2) yes
C6 . N1 . H11 . 115.5 no
C1 . N1 . H11 . 114.9 no
C11 . N2 . C10 . 115.9(2) yes
C11 . N2 . C9 . 124.1(2) yes
C10 . N2 . C9 . 119.9(2) yes
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
N1 . H11 . O1 2_667 175.52 0.871 1.998 2.868(4) yes
C2 . H21 . O2 . 131.97 0.971 2.424 3.157(4) yes
C10 . H101 . O2 2_756 146.60 0.945 2.404 3.235(4) yes
_database_code_depnum_ccdc_archive 'CCDC 1018879'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_6-cis
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6303
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   7.71325(7)
_cell_length_b                   8.16076(7)
_cell_length_c                   23.7540(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.6857(8)
_cell_angle_gamma                90
_cell_volume                     1490.22(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  '-P 2yn'

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 0.0181 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'
S 0.3331 0.5567 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 = C13 H20 N2 O3 S2 
# Dc =      1.41 Fooo =    672.00 Mu =     33.23 M =    316.45
# Found Formula = C13 H20 N2 O3 S2 
# Dc =      1.41 FOOO =    672.00 Mu =     33.23 M =    316.45

_chemical_formula_sum            'C13 H20 N2 O3 S2'
_chemical_formula_moiety         'C13 H20 N2 O3 S2'
_chemical_compound_source        .
_chemical_formula_weight         316.45


_cell_measurement_reflns_used    14802
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.32

_exptl_crystal_density_diffrn    1.410
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    3.323

# Sheldrick geometric approximatio 0.59 0.77 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.44
_exptl_absorpt_correction_T_max  0.77
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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    'SIR92 (Altomare et al., 1994)'
_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            19616
_reflns_number_total             3107
_diffrn_reflns_av_R_equivalents  0.021
# Number of reflections with Friedels Law is 3107 
# Theoretical number of reflections is about 6251 


_diffrn_reflns_theta_min         3.734
_diffrn_reflns_theta_max         76.356
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        74.828
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              29

_oxford_diffrn_Wilson_B_factor   1.81
_oxford_diffrn_Wilson_scale      0.04

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

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.29


# 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         3107
_refine_ls_number_restraints     0
_refine_ls_number_parameters     181
_oxford_refine_ls_R_factor_ref   0.0265
_refine_ls_wR_factor_ref         0.1080
_refine_ls_goodness_of_fit_ref   0.9997
_refine_ls_shift/su_max          0.0016334
_refine_ls_shift/su_mean         0.0003044


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3107
_refine_ls_R_factor_all          0.0265
_refine_ls_wR_factor_all         0.1080

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2987
_refine_ls_R_factor_gt           0.0257
_refine_ls_wR_factor_gt          0.1049

# 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 .


_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) + ( 0.10P)² + 0.00P] 
 ,where P=p(6)*max(Fo²,0) + (1-p(6))Fc² 
;

# 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
C1 C 0.77413(14) 0.50991(12) 0.24176(4) 0.0213 1.0000 Uani . . . . . .
C2 C 0.72960(13) 0.56238(11) 0.30062(4) 0.0198 1.0000 Uani . . . . . .
C3 C 0.59720(14) 0.44457(12) 0.32389(4) 0.0243 1.0000 Uani . . . . . .
C4 C 0.41025(14) 0.48993(14) 0.30373(5) 0.0270 1.0000 Uani . . . . . .
C5 C 0.36291(14) 0.46624(15) 0.24063(5) 0.0265 1.0000 Uani . . . . . .
C6 C 0.46744(13) 0.57635(12) 0.20332(4) 0.0221 1.0000 Uani . . . . . .
C7 C 0.38052(13) 0.57444(12) 0.14361(4) 0.0229 1.0000 Uani . . . . . .
C8 C 0.11707(17) 0.63143(18) 0.08957(5) 0.0400 1.0000 Uani . . . . . .
C9 C 0.88640(13) 0.66961(12) 0.40438(4) 0.0205 1.0000 Uani . . . . . .
C10 C 1.01300(15) 0.76210(13) 0.49737(4) 0.0243 1.0000 Uani . . . . . .
C11 C 1.20279(15) 0.78166(15) 0.51907(5) 0.0289 1.0000 Uani . . . . . .
C12 C 1.29482(14) 0.63776(14) 0.49318(4) 0.0276 1.0000 Uani . . . . . .
C13 C 1.19927(14) 0.62014(13) 0.43472(4) 0.0240 1.0000 Uani . . . . . .
S1 S 0.69349(3) 0.75618(3) 0.413365(10) 0.0242 1.0000 Uani . . . . . .
S3 S 0.93781(3) 0.56343(3) 0.342649(9) 0.0225 1.0000 Uani . . . . . .
O1 O 0.91728(10) 0.45357(11) 0.23374(3) 0.0289 1.0000 Uani . . . . . .
O2 O 0.44097(11) 0.51537(12) 0.10341(3) 0.0344 1.0000 Uani . . . . . .
O3 O 0.22423(11) 0.64347(13) 0.14219(4) 0.0387 1.0000 Uani . . . . . .
N1 N 0.64682(11) 0.52202(12) 0.19939(4) 0.0225 1.0000 Uani . . . . . .
N2 N 1.02108(11) 0.67479(10) 0.44318(3) 0.0212 1.0000 Uani . . . . . .
H11 H 0.6688 0.4865 0.1671 0.0287 1.0000 Uiso R . . . . .
H21 H 0.6826 0.6690 0.3000 0.0249 1.0000 Uiso R . . . . .
H31 H 0.6228 0.3306 0.3123 0.0280 1.0000 Uiso R . . . . .
H32 H 0.6115 0.4544 0.3648 0.0291 1.0000 Uiso R . . . . .
H41 H 0.3945 0.6043 0.3117 0.0322 1.0000 Uiso R . . . . .
H42 H 0.3341 0.4276 0.3238 0.0326 1.0000 Uiso R . . . . .
H51 H 0.2441 0.4965 0.2332 0.0311 1.0000 Uiso R . . . . .
H52 H 0.3782 0.3548 0.2300 0.0322 1.0000 Uiso R . . . . .
H61 H 0.4639 0.6874 0.2162 0.0248 1.0000 Uiso R . . . . .
H81 H 0.0843 0.5244 0.0827 0.0595 1.0000 Uiso R . . . . .
H82 H 0.0180 0.6952 0.0922 0.0612 1.0000 Uiso R . . . . .
H83 H 0.1827 0.6720 0.0606 0.0615 1.0000 Uiso R . . . . .
H101 H 0.9543 0.8657 0.4900 0.0290 1.0000 Uiso R . . . . .
H102 H 0.9468 0.6954 0.5228 0.0306 1.0000 Uiso R . . . . .
H111 H 1.2185 0.7793 0.5596 0.0368 1.0000 Uiso R . . . . .
H112 H 1.2440 0.8821 0.5067 0.0364 1.0000 Uiso R . . . . .
H121 H 1.2736 0.5418 0.5149 0.0336 1.0000 Uiso R . . . . .
H122 H 1.4195 0.6526 0.4915 0.0344 1.0000 Uiso R . . . . .
H131 H 1.1987 0.5113 0.4199 0.0278 1.0000 Uiso R . . . . .
H132 H 1.2475 0.6901 0.4079 0.0295 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0187(5) 0.0224(5) 0.0224(5) -0.0004(3) 0.0005(4) -0.0023(4)
C2 0.0181(5) 0.0213(5) 0.0195(5) -0.0001(3) -0.0012(4) -0.0004(3)
C3 0.0228(5) 0.0257(5) 0.0242(5) 0.0013(4) 0.0013(4) -0.0034(4)
C4 0.0211(5) 0.0338(6) 0.0264(5) -0.0014(4) 0.0046(4) -0.0048(4)
C5 0.0182(5) 0.0322(5) 0.0292(5) -0.0033(4) 0.0023(4) -0.0044(4)
C6 0.0162(5) 0.0261(5) 0.0235(5) -0.0040(3) -0.0013(4) 0.0015(4)
C7 0.0182(5) 0.0234(5) 0.0262(5) -0.0021(3) -0.0028(4) 0.0016(4)
C8 0.0248(6) 0.0576(8) 0.0352(6) -0.0081(5) -0.0131(5) 0.0094(6)
C9 0.0206(5) 0.0210(4) 0.0196(4) 0.0008(3) -0.0001(3) -0.0006(3)
C10 0.0231(6) 0.0285(5) 0.0211(5) -0.0032(3) 0.0006(4) -0.0009(4)
C11 0.0263(6) 0.0347(5) 0.0247(5) -0.0042(4) -0.0051(4) -0.0002(4)
C12 0.0221(5) 0.0343(5) 0.0254(5) 0.0017(4) -0.0038(4) 0.0015(4)
C13 0.0190(5) 0.0294(5) 0.0234(5) -0.0007(4) 0.0000(4) 0.0026(4)
S1 0.01894(19) 0.02836(19) 0.02521(19) -0.00202(8) 0.00037(12) 0.00322(8)
S3 0.01801(19) 0.02858(19) 0.02038(18) -0.00395(8) -0.00238(12) 0.00281(8)
O1 0.0179(4) 0.0409(5) 0.0274(4) -0.0070(3) -0.0007(3) 0.0032(3)
O2 0.0300(5) 0.0494(5) 0.0232(4) -0.0032(3) -0.0023(3) 0.0122(4)
O3 0.0244(5) 0.0571(6) 0.0326(4) -0.0137(4) -0.0102(3) 0.0166(4)
N1 0.0171(5) 0.0302(4) 0.0201(4) -0.0039(3) 0.0004(3) 0.0010(3)
N2 0.0183(4) 0.0245(4) 0.0204(4) -0.0018(3) -0.0007(3) 0.0018(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.07(13)
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
C1 . C2 . 1.5281(14) yes
C1 . O1 . 1.2252(13) yes
C1 . N1 . 1.3511(13) yes
C2 . C3 . 1.5378(14) yes
C2 . S3 . 1.8204(10) yes
C2 . H21 . 0.942 no
C3 . C4 . 1.5274(15) yes
C3 . H31 . 0.995 no
C3 . H32 . 0.973 no
C4 . C5 . 1.5258(14) yes
C4 . H41 . 0.962 no
C4 . H42 . 0.937 no
C5 . C6 . 1.5361(15) yes
C5 . H51 . 0.952 no
C5 . H52 . 0.954 no
C6 . C7 . 1.5187(14) yes
C6 . N1 . 1.4631(13) yes
C6 . H61 . 0.958 no
C7 . O2 . 1.1977(14) yes
C7 . O3 . 1.3286(13) yes
C8 . O3 . 1.4445(13) yes
C8 . H81 . 0.920 no
C8 . H82 . 0.931 no
C8 . H83 . 0.948 no
C9 . S1 . 1.6765(11) yes
C9 . S3 . 1.7757(10) yes
C9 . N2 . 1.3320(13) yes
C10 . C11 . 1.5202(16) yes
C10 . N2 . 1.4769(12) yes
C10 . H101 . 0.968 no
C10 . H102 . 0.985 no
C11 . C12 . 1.5272(16) yes
C11 . H111 . 0.960 no
C11 . H112 . 0.935 no
C12 . C13 . 1.5247(13) yes
C12 . H121 . 0.960 no
C12 . H122 . 0.973 no
C13 . N2 . 1.4743(13) yes
C13 . H131 . 0.955 no
C13 . H132 . 0.954 no
N1 . H11 . 0.850 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 . C1 . O1 . 121.34(9) yes
C2 . C1 . N1 . 117.20(9) yes
O1 . C1 . N1 . 121.41(10) yes
C1 . C2 . C3 . 111.05(8) yes
C1 . C2 . S3 . 104.42(7) yes
C3 . C2 . S3 . 112.82(7) yes
C1 . C2 . H21 . 111.1 no
C3 . C2 . H21 . 108.5 no
S3 . C2 . H21 . 109.0 no
C2 . C3 . C4 . 111.93(8) yes
C2 . C3 . H31 . 109.4 no
C4 . C3 . H31 . 110.1 no
C2 . C3 . H32 . 106.4 no
C4 . C3 . H32 . 108.7 no
H31 . C3 . H32 . 110.2 no
C3 . C4 . C5 . 114.92(9) yes
C3 . C4 . H41 . 107.7 no
C5 . C4 . H41 . 107.0 no
C3 . C4 . H42 . 108.9 no
C5 . C4 . H42 . 108.8 no
H41 . C4 . H42 . 109.4 no
C4 . C5 . C6 . 113.45(9) yes
C4 . C5 . H51 . 107.4 no
C6 . C5 . H51 . 106.5 no
C4 . C5 . H52 . 110.9 no
C6 . C5 . H52 . 108.8 no
H51 . C5 . H52 . 109.6 no
C5 . C6 . C7 . 108.69(8) yes
C5 . C6 . N1 . 113.78(9) yes
C7 . C6 . N1 . 106.55(8) yes
C5 . C6 . H61 . 109.8 no
C7 . C6 . H61 . 106.6 no
N1 . C6 . H61 . 111.0 no
C6 . C7 . O2 . 125.30(10) yes
C6 . C7 . O3 . 110.47(9) yes
O2 . C7 . O3 . 124.20(10) yes
O3 . C8 . H81 . 110.3 no
O3 . C8 . H82 . 108.6 no
H81 . C8 . H82 . 109.1 no
O3 . C8 . H83 . 107.7 no
H81 . C8 . H83 . 111.0 no
H82 . C8 . H83 . 110.1 no
S1 . C9 . S3 . 124.83(6) yes
S1 . C9 . N2 . 123.27(8) yes
S3 . C9 . N2 . 111.89(8) yes
C11 . C10 . N2 . 103.78(9) yes
C11 . C10 . H101 . 113.1 no
N2 . C10 . H101 . 108.5 no
C11 . C10 . H102 . 112.5 no
N2 . C10 . H102 . 109.1 no
H101 . C10 . H102 . 109.5 no
C10 . C11 . C12 . 104.42(8) yes
C10 . C11 . H111 . 112.2 no
C12 . C11 . H111 . 111.3 no
C10 . C11 . H112 . 109.1 no
C12 . C11 . H112 . 111.5 no
H111 . C11 . H112 . 108.3 no
C11 . C12 . C13 . 103.49(8) yes
C11 . C12 . H121 . 107.8 no
C13 . C12 . H121 . 108.8 no
C11 . C12 . H122 . 114.4 no
C13 . C12 . H122 . 112.4 no
H121 . C12 . H122 . 109.6 no
C12 . C13 . N2 . 103.53(8) yes
C12 . C13 . H131 . 114.2 no
N2 . C13 . H131 . 110.8 no
C12 . C13 . H132 . 111.5 no
N2 . C13 . H132 . 109.2 no
H131 . C13 . H132 . 107.5 no
C2 . S3 . C9 . 102.04(5) yes
C8 . O3 . C7 . 116.55(9) yes
C6 . N1 . C1 . 127.46(9) yes
C6 . N1 . H11 . 114.8 no
C1 . N1 . H11 . 117.4 no
C10 . N2 . C13 . 111.77(8) yes
C10 . N2 . C9 . 122.17(9) yes
C13 . N2 . C9 . 125.39(8) yes
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
C2 . H21 . O1 3_655 161.81 0.942 2.555 3.4627(15) yes
C4 . H42 . O3 3_545 143.39 0.937 2.508 3.3072(15) yes
C5 . H51 . O1 1_455 154.39 0.952 2.546 3.4293(15) yes
_database_code_depnum_ccdc_archive 'CCDC 1018880'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_7
#==============================================================================
_audit_creation_date             14-05-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 6294
_chemical_name_systematic        .
_chemical_melting_point          'not measured'

_cell_length_a                   6.2079(4)
_cell_length_b                   7.7139(7)
_cell_length_c                   8.6278(8)
_cell_angle_alpha                82.686(8)
_cell_angle_beta                 88.718(7)
_cell_angle_gamma                89.279(6)
_cell_volume                     409.68(6)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-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 0.0181 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            2

# Given Formula = C8 H11 N1 O3 
# Dc =      1.37 Fooo =    180.00 Mu =      8.84 M =    169.18
# Found Formula = C8 H11 N1 O3 
# Dc =      1.37 FOOO =    180.00 Mu =      8.84 M =    169.18

_chemical_formula_sum            'C8 H11 N1 O3'
_chemical_formula_moiety         'C8 H11 N1 O3'
_chemical_compound_source        .
_chemical_formula_weight         169.18


_cell_measurement_reflns_used    2613
_cell_measurement_theta_min      5
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             180
_exptl_absorpt_coefficient_mu    0.884

# Sheldrick geometric approximatio 0.84 0.84 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.84
_diffrn_measurement_device_type  'Oxford Diffraction Gemini'
_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    'SIR92 (Altomare et al., 1994)'
_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            3072
_reflns_number_total             1671
_diffrn_reflns_av_R_equivalents  0.011
# Number of reflections with Friedels Law is 1671 
# Theoretical number of reflections is about 3411 


_diffrn_reflns_theta_min         5.170
_diffrn_reflns_theta_max         75.764
_diffrn_measured_fraction_theta_max 0.973

_diffrn_reflns_theta_full        70.000
_diffrn_measured_fraction_theta_full 0.989


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              -9
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              10

_oxford_diffrn_Wilson_B_factor   1.73
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.23


# 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         1671
_refine_ls_number_restraints     0
_refine_ls_number_parameters     109
_oxford_refine_ls_R_factor_ref   0.0338
_refine_ls_wR_factor_ref         0.0895
_refine_ls_goodness_of_fit_ref   1.0124
_refine_ls_shift/su_max          0.0010934
_refine_ls_shift/su_mean         0.0002736


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1671
_refine_ls_R_factor_all          0.0338
_refine_ls_wR_factor_all         0.0895

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1592
_refine_ls_R_factor_gt           0.0327
_refine_ls_wR_factor_gt          0.0883

# 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 .


_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) + ( 0.05P)² + 0.14P] 
 ,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
C1 C 0.84821(16) 0.76518(14) 0.57389(12) 0.0198 1.0000 Uani . . . . . .
C2 C 0.75550(18) 0.59020(14) 0.62319(13) 0.0245 1.0000 Uani . . . . . .
C3 C 0.56800(19) 0.54236(15) 0.69335(13) 0.0267 1.0000 Uani . . . . . .
C4 C 0.38683(18) 0.64732(16) 0.75174(14) 0.0284 1.0000 Uani . . . . . .
C5 C 0.40836(18) 0.84514(16) 0.72783(14) 0.0267 1.0000 Uani . . . . . .
C6 C 0.62978(17) 0.91214(14) 0.76693(12) 0.0211 1.0000 Uani . . . . . .
C7 C 0.70417(17) 0.82832(13) 0.92724(12) 0.0213 1.0000 Uani . . . . . .
C8 C 0.9987(2) 0.73965(17) 1.08661(14) 0.0316 1.0000 Uani . . . . . .
O1 O 0.98830(13) 0.77850(10) 0.46741(9) 0.0260 1.0000 Uani . . . . . .
O2 O 0.58130(13) 0.78939(11) 1.03584(9) 0.0299 1.0000 Uani . . . . . .
O3 O 0.91773(12) 0.81114(11) 0.93546(9) 0.0256 1.0000 Uani . . . . . .
N1 N 0.78968(14) 0.90523(11) 0.64269(10) 0.0204 1.0000 Uani . . . . . .
H11 H 0.8591 1.0016 0.6077 0.0254 1.0000 Uiso R . . . . .
H21 H 0.8469 0.4976 0.5944 0.0298 1.0000 Uiso R . . . . .
H31 H 0.5438 0.4219 0.7089 0.0318 1.0000 Uiso R . . . . .
H41 H 0.3694 0.6104 0.8631 0.0340 1.0000 Uiso R . . . . .
H42 H 0.2502 0.6165 0.7022 0.0348 1.0000 Uiso R . . . . .
H51 H 0.3034 0.8943 0.7948 0.0324 1.0000 Uiso R . . . . .
H52 H 0.3802 0.8897 0.6210 0.0324 1.0000 Uiso R . . . . .
H61 H 0.6116 1.0340 0.7801 0.0253 1.0000 Uiso R . . . . .
H81 H 1.1499 0.7420 1.0807 0.0463 1.0000 Uiso R . . . . .
H82 H 0.9507 0.6225 1.1107 0.0481 1.0000 Uiso R . . . . .
H83 H 0.9453 0.8004 1.1643 0.0451 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0193(5) 0.0231(5) 0.0163(5) 0.0003(4) -0.0007(4) -0.0006(4)
C2 0.0284(6) 0.0221(5) 0.0226(5) -0.0014(4) 0.0014(4) -0.0007(4)
C3 0.0310(6) 0.0239(5) 0.0246(5) 0.0005(4) -0.0016(4) -0.0070(4)
C4 0.0199(5) 0.0357(6) 0.0286(6) 0.0003(5) -0.0002(4) -0.0072(4)
C5 0.0186(5) 0.0329(6) 0.0268(6) 0.0030(4) 0.0006(4) 0.0013(4)
C6 0.0207(5) 0.0212(5) 0.0204(5) -0.0003(4) 0.0043(4) 0.0002(4)
C7 0.0221(5) 0.0214(5) 0.0203(5) -0.0030(4) 0.0034(4) -0.0022(4)
C8 0.0285(6) 0.0417(7) 0.0231(6) 0.0025(5) -0.0047(4) -0.0047(5)
O1 0.0292(4) 0.0261(4) 0.0222(4) -0.0028(3) 0.0084(3) -0.0027(3)
O2 0.0266(4) 0.0393(5) 0.0219(4) 0.0026(3) 0.0076(3) -0.0017(3)
O3 0.0206(4) 0.0358(4) 0.0195(4) 0.0005(3) 0.0007(3) -0.0029(3)
N1 0.0221(4) 0.0204(4) 0.0179(4) 0.0005(3) 0.0044(3) -0.0036(3)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          31(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
C1 . C2 . 1.4821(15) yes
C1 . O1 . 1.2463(13) yes
C1 . N1 . 1.3398(14) yes
C2 . C3 . 1.3341(16) yes
C2 . H21 . 0.960 no
C3 . C4 . 1.4932(17) yes
C3 . H31 . 0.936 no
C4 . C5 . 1.5208(17) yes
C4 . H41 . 0.971 no
C4 . H42 . 1.003 no
C5 . C6 . 1.5340(15) yes
C5 . H51 . 0.967 no
C5 . H52 . 0.961 no
C6 . C7 . 1.5290(14) yes
C6 . N1 . 1.4500(13) yes
C6 . H61 . 0.966 no
C7 . O2 . 1.2050(13) yes
C7 . O3 . 1.3333(13) yes
C8 . O3 . 1.4479(13) yes
C8 . H81 . 0.939 no
C8 . H82 . 0.951 no
C8 . H83 . 0.919 no
N1 . H11 . 0.880 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 . C1 . O1 . 117.81(9) yes
C2 . C1 . N1 . 122.02(9) yes
O1 . C1 . N1 . 120.14(9) yes
C1 . C2 . C3 . 131.30(11) yes
C1 . C2 . H21 . 112.3 no
C3 . C2 . H21 . 116.3 no
C2 . C3 . C4 . 131.46(11) yes
C2 . C3 . H31 . 115.1 no
C4 . C3 . H31 . 113.4 no
C3 . C4 . C5 . 117.38(9) yes
C3 . C4 . H41 . 107.4 no
C5 . C4 . H41 . 107.9 no
C3 . C4 . H42 . 108.8 no
C5 . C4 . H42 . 108.3 no
H41 . C4 . H42 . 106.6 no
C4 . C5 . C6 . 114.75(9) yes
C4 . C5 . H51 . 108.5 no
C6 . C5 . H51 . 107.1 no
C4 . C5 . H52 . 110.0 no
C6 . C5 . H52 . 107.5 no
H51 . C5 . H52 . 108.8 no
C5 . C6 . C7 . 111.73(9) yes
C5 . C6 . N1 . 113.38(9) yes
C7 . C6 . N1 . 113.94(9) yes
C5 . C6 . H61 . 107.1 no
C7 . C6 . H61 . 103.4 no
N1 . C6 . H61 . 106.4 no
C6 . C7 . O2 . 122.81(10) yes
C6 . C7 . O3 . 113.02(9) yes
O2 . C7 . O3 . 124.10(10) yes
O3 . C8 . H81 . 108.1 no
O3 . C8 . H82 . 108.9 no
H81 . C8 . H82 . 110.0 no
O3 . C8 . H83 . 111.3 no
H81 . C8 . H83 . 111.7 no
H82 . C8 . H83 . 106.9 no
C8 . O3 . C7 . 115.60(9) yes
C6 . N1 . C1 . 127.04(9) yes
C6 . N1 . H11 . 118.3 no
C1 . N1 . H11 . 114.7 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
N1 . H11 . O1 2_776 178.62 0.880 1.982 2.8618(16) yes
C2 . H21 . O1 2_766 167.69 0.960 2.466 3.4097(16) yes
C6 . H61 . O2 2_677 137.64 0.966 2.497 3.2765(16) yes


_database_code_depnum_ccdc_archive 'CCDC 1018881'
