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

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

data_kel1511SN
_database_code_depnum_ccdc_archive 'CCDC 1590267'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             15-09-09
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1511SN\Tony_kel1511SN_data At 14:56 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.8798(1)
_cell_length_b                   18.4104(1)
_cell_length_c                   14.5081(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2905.99(4)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c c n '
_symmetry_space_group_name_Hall  '-P 2ab 2ac '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y,z+1/2
x+1/2,-y,-z+1/2
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y+1/2,z
x+1/2,y+1/2,-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            8

# Given Formula = C19 H14 N2 O3 
# Dc =      1.46 Fooo =   1328.00 Mu =      8.19 M =    318.33
# Found Formula = C19 H14 N2 O3 
# Dc =      1.46 FOOO =   1328.00 Mu =      8.19 M =    318.33

_chemical_formula_sum            'C19 H14 N2 O3'
_chemical_formula_moiety         'C19 H14 N2 O3'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         318.33


_cell_measurement_reflns_used    33874
_cell_measurement_theta_min      5
_cell_measurement_theta_max      72
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_max          0.359

_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    0.819

# Sheldrick geometric approximatio 0.89 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2' ####
_diffrn_radiation_source         
'Supernova (Cu) X-ray Source' ################
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_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    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            54126
_reflns_number_total             2881
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2881 
# Theoretical number of reflections is about 5746 


_diffrn_reflns_theta_min         4.721
_diffrn_reflns_theta_max         72.334
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        72.334
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              0
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              22
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.08
_oxford_diffrn_Wilson_scale      0.05

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

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.26


# 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>-10.0\s(I)
_refine_ls_number_reflns         2881
_refine_ls_number_restraints     0
_refine_ls_number_parameters     259
_oxford_refine_ls_R_factor_ref   0.0316
_refine_ls_wR_factor_ref         0.0746
_refine_ls_goodness_of_fit_ref   1.0045
_refine_ls_shift/su_max          0.0005888
_refine_ls_shift/su_mean         0.0001237


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2881
_refine_ls_R_factor_all          0.0316
_refine_ls_wR_factor_all         0.0746

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2749
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_gt          0.0734

# 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    refxyz #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 1.27P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

The H atoms were all located in a difference electron density map, but those 
attached to carbon atoms were repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98, N---H = 0.86 Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined without restraints
and the displacement parameters were held fixed. 

The largest peaks in the final difference electron density map
are located midway between bonded atoms.


;

# 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 0.50365(7) 0.58845(4) 0.61484(5) 0.0251 1.0000 Uani . . . . . .
O2 O 0.67716(7) 0.32450(4) 0.61103(5) 0.0228 1.0000 Uani . . . . . .
O3 O 0.78885(7) 0.38389(5) 0.71880(5) 0.0285 1.0000 Uani . . . . . .
N1 N 0.73349(8) 0.47362(5) 0.52103(6) 0.0203 1.0000 Uani . . . . . .
N2 N 0.51615(8) 0.46064(5) 0.71967(6) 0.0193 1.0000 Uani . . . . . .
C1 C 0.73329(9) 0.53176(5) 0.45938(7) 0.0201 1.0000 Uani . . . . . .
C2 C 0.80578(10) 0.54051(6) 0.38064(8) 0.0256 1.0000 Uani . . . . . .
C3 C 0.79101(11) 0.60346(6) 0.32961(8) 0.0275 1.0000 Uani . . . . . .
C4 C 0.70570(11) 0.65694(6) 0.35486(8) 0.0262 1.0000 Uani . . . . . .
C5 C 0.63386(10) 0.64836(6) 0.43263(7) 0.0233 1.0000 Uani . . . . . .
C6 C 0.64823(9) 0.58526(5) 0.48530(7) 0.0201 1.0000 Uani . . . . . .
C7 C 0.58464(9) 0.55896(5) 0.56750(7) 0.0195 1.0000 Uani . . . . . .
C8 C 0.63907(9) 0.48778(5) 0.58578(7) 0.0186 1.0000 Uani . . . . . .
C9 C 0.60774(9) 0.44515(5) 0.65822(7) 0.0181 1.0000 Uani . . . . . .
C10 C 0.66678(9) 0.37285(6) 0.68573(7) 0.0203 1.0000 Uani . . . . . .
C11 C 0.58273(9) 0.34725(6) 0.76115(7) 0.0210 1.0000 Uani . . . . . .
C12 C 0.57949(11) 0.28216(6) 0.80827(8) 0.0259 1.0000 Uani . . . . . .
C13 C 0.49135(12) 0.27333(7) 0.87713(8) 0.0305 1.0000 Uani . . . . . .
C14 C 0.41087(11) 0.32961(7) 0.89863(8) 0.0295 1.0000 Uani . . . . . .
C15 C 0.41288(10) 0.39534(6) 0.85065(7) 0.0244 1.0000 Uani . . . . . .
C16 C 0.49847(9) 0.40220(6) 0.78042(7) 0.0199 1.0000 Uani . . . . . .
C17 C 0.76425(10) 0.40055(6) 0.48791(7) 0.0237 1.0000 Uani . . . . . .
C18 C 0.78849(10) 0.34568(6) 0.56393(8) 0.0254 1.0000 Uani . . . . . .
C19 C 0.87068(10) 0.37249(7) 0.64240(9) 0.0308 1.0000 Uani . . . . . .
H2 H 0.4672(13) 0.4986(8) 0.7127(9) 0.0257 1.0000 Uiso . . . . . .
H21 H 0.8649(13) 0.5023(8) 0.3613(9) 0.0319 1.0000 Uiso . . . . . .
H31 H 0.8406(13) 0.6102(8) 0.2733(10) 0.0331 1.0000 Uiso . . . . . .
H41 H 0.6945(12) 0.6995(8) 0.3160(10) 0.0306 1.0000 Uiso . . . . . .
H51 H 0.5711(13) 0.6847(7) 0.4506(9) 0.0279 1.0000 Uiso . . . . . .
H121 H 0.6361(13) 0.2417(8) 0.7932(9) 0.0300 1.0000 Uiso . . . . . .
H131 H 0.4862(14) 0.2267(8) 0.9076(10) 0.0372 1.0000 Uiso . . . . . .
H141 H 0.3508(14) 0.3226(8) 0.9485(10) 0.0357 1.0000 Uiso . . . . . .
H151 H 0.3538(13) 0.4351(8) 0.8641(9) 0.0289 1.0000 Uiso . . . . . .
H171 H 0.6983(13) 0.3821(7) 0.4465(9) 0.0277 1.0000 Uiso . . . . . .
H172 H 0.8415(13) 0.4040(7) 0.4520(10) 0.0278 1.0000 Uiso . . . . . .
H181 H 0.8204(13) 0.3012(8) 0.5360(9) 0.0296 1.0000 Uiso . . . . . .
H191 H 0.9319(14) 0.3361(8) 0.6614(10) 0.0376 1.0000 Uiso . . . . . .
H192 H 0.9131(14) 0.4199(8) 0.6267(10) 0.0374 1.0000 Uiso . . . . . .


_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.19(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
O1 . C7 . 1.2422(13) yes
O2 . C10 . 1.4071(12) yes
O2 . C18 . 1.4443(12) yes
O3 . C10 . 1.4266(12) yes
O3 . C19 . 1.4371(14) yes
N1 . C1 . 1.3948(13) yes
N1 . C8 . 1.4163(13) yes
N1 . C17 . 1.4671(13) yes
N2 . C9 . 1.3671(13) yes
N2 . C16 . 1.4039(13) yes
N2 . H2 . 0.884(15) no
C1 . C2 . 1.3975(15) yes
C1 . C6 . 1.4028(15) yes
C2 . C3 . 1.3846(16) yes
C2 . H21 . 0.994(15) no
C3 . C4 . 1.4019(17) yes
C3 . H31 . 0.986(15) no
C4 . C5 . 1.3815(16) yes
C4 . H41 . 0.973(14) no
C5 . C6 . 1.3993(15) yes
C5 . H51 . 0.990(14) no
C6 . C7 . 1.4612(14) yes
C7 . C8 . 1.4624(14) yes
C8 . C9 . 1.3551(14) yes
C9 . C10 . 1.5309(14) yes
C10 . C11 . 1.5019(14) yes
C11 . C12 . 1.3800(15) yes
C11 . C16 . 1.3936(15) yes
C12 . C13 . 1.3944(16) yes
C12 . H121 . 0.991(15) no
C13 . C14 . 1.3919(17) yes
C13 . H131 . 0.968(15) no
C14 . C15 . 1.3962(16) yes
C14 . H141 . 0.983(15) no
C15 . C16 . 1.3861(15) yes
C15 . H151 . 0.994(14) no
C17 . C18 . 1.5187(15) yes
C17 . H171 . 0.996(14) no
C17 . H172 . 0.991(14) no
C18 . C19 . 1.5294(17) yes
C18 . H181 . 0.977(14) no
C19 . H191 . 0.985(16) no
C19 . H192 . 1.014(16) 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
C10 . O2 . C18 . 105.12(8) yes
C10 . O3 . C19 . 107.25(8) yes
C1 . N1 . C8 . 106.44(8) yes
C1 . N1 . C17 . 119.61(8) yes
C8 . N1 . C17 . 123.46(8) yes
C9 . N2 . C16 . 110.46(8) yes
C9 . N2 . H2 . 121.9(9) no
C16 . N2 . H2 . 126.5(9) no
N1 . C1 . C2 . 127.71(10) yes
N1 . C1 . C6 . 111.59(9) yes
C2 . C1 . C6 . 120.70(10) yes
C1 . C2 . C3 . 117.91(10) yes
C1 . C2 . H21 . 121.0(8) no
C3 . C2 . H21 . 121.1(8) no
C2 . C3 . C4 . 121.66(10) yes
C2 . C3 . H31 . 119.0(8) no
C4 . C3 . H31 . 119.4(8) no
C3 . C4 . C5 . 120.51(10) yes
C3 . C4 . H41 . 119.8(8) no
C5 . C4 . H41 . 119.7(8) no
C4 . C5 . C6 . 118.54(10) yes
C4 . C5 . H51 . 121.8(8) no
C6 . C5 . H51 . 119.6(8) no
C1 . C6 . C5 . 120.68(10) yes
C1 . C6 . C7 . 107.37(9) yes
C5 . C6 . C7 . 131.91(10) yes
C6 . C7 . O1 . 129.97(9) yes
C6 . C7 . C8 . 104.67(8) yes
O1 . C7 . C8 . 125.35(9) yes
C7 . C8 . N1 . 109.77(8) yes
C7 . C8 . C9 . 123.90(9) yes
N1 . C8 . C9 . 126.18(9) yes
N2 . C9 . C8 . 124.63(9) yes
N2 . C9 . C10 . 108.49(8) yes
C8 . C9 . C10 . 126.88(9) yes
C9 . C10 . O3 . 110.76(8) yes
C9 . C10 . O2 . 112.51(8) yes
O3 . C10 . O2 . 105.93(8) yes
C9 . C10 . C11 . 101.97(8) yes
O3 . C10 . C11 . 111.50(8) yes
O2 . C10 . C11 . 114.30(8) yes
C10 . C11 . C12 . 130.46(10) yes
C10 . C11 . C16 . 108.59(9) yes
C12 . C11 . C16 . 120.95(10) yes
C11 . C12 . C13 . 118.27(10) yes
C11 . C12 . H121 . 121.8(8) no
C13 . C12 . H121 . 119.9(8) no
C12 . C13 . C14 . 120.42(11) yes
C12 . C13 . H131 . 118.1(9) no
C14 . C13 . H131 . 121.5(9) no
C13 . C14 . C15 . 121.57(10) yes
C13 . C14 . H141 . 119.1(9) no
C15 . C14 . H141 . 119.4(9) no
C14 . C15 . C16 . 117.13(10) yes
C14 . C15 . H151 . 122.0(8) no
C16 . C15 . H151 . 120.8(8) no
N2 . C16 . C11 . 109.89(9) yes
N2 . C16 . C15 . 128.56(10) yes
C11 . C16 . C15 . 121.55(10) yes
N1 . C17 . C18 . 114.31(9) yes
N1 . C17 . H171 . 110.2(8) no
C18 . C17 . H171 . 109.7(8) no
N1 . C17 . H172 . 107.8(8) no
C18 . C17 . H172 . 106.1(8) no
H171 . C17 . H172 . 108.4(11) no
C17 . C18 . O2 . 112.18(9) yes
C17 . C18 . C19 . 115.31(10) yes
O2 . C18 . C19 . 103.02(9) yes
C17 . C18 . H181 . 108.6(8) no
O2 . C18 . H181 . 105.5(8) no
C19 . C18 . H181 . 111.8(8) no
C18 . C19 . O3 . 105.01(9) yes
C18 . C19 . H191 . 112.6(9) no
O3 . C19 . H191 . 107.6(9) no
C18 . C19 . H192 . 112.1(8) no
O3 . C19 . H192 . 109.2(8) no
H191 . C19 . H192 . 110.0(12) 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
N2 . H2 . O1 . 123.8(11) 0.884(15) 2.216(15) 2.8051(15) yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O2 C10 O3 -37.99(10) . . . . no
C18 O2 C10 C9 83.17(9) . . . . no
C18 O2 C10 C11 -161.15(8) . . . . no
C10 O2 C18 C17 -91.67(10) . . . . no
C10 O2 C18 C19 32.94(10) . . . . no
C19 O3 C10 O2 27.09(11) . . . . no
C19 O3 C10 C9 -95.19(10) . . . . no
C19 O3 C10 C11 152.01(9) . . . . no
C10 O3 C19 C18 -6.01(12) . . . . no
C8 N1 C1 C2 -176.44(10) . . . . no
C8 N1 C1 C6 4.04(11) . . . . no
C17 N1 C1 C2 -30.46(15) . . . . no
C17 N1 C1 C6 150.02(9) . . . . no
C1 N1 C8 C7 -4.00(11) . . . . no
C1 N1 C8 C9 -179.72(10) . . . . no
C17 N1 C8 C7 -148.33(9) . . . . no
C17 N1 C8 C9 35.95(15) . . . . no
C1 N1 C17 C18 167.30(9) . . . . no
C8 N1 C17 C18 -52.74(13) . . . . no
C16 N2 C9 C8 173.79(10) . . . . no
C16 N2 C9 C10 -6.30(11) . . . . no
C9 N2 C16 C11 1.94(12) . . . . no
C9 N2 C16 C15 -177.99(10) . . . . no
N1 C1 C2 C3 -179.34(10) . . . . no
C6 C1 C2 C3 0.15(16) . . . . no
N1 C1 C6 C5 179.83(9) . . . . no
N1 C1 C6 C7 -2.49(11) . . . . no
C2 C1 C6 C5 0.26(15) . . . . no
C2 C1 C6 C7 177.94(9) . . . . no
C1 C2 C3 C4 -0.51(17) . . . . no
C2 C3 C4 C5 0.46(18) . . . . no
C3 C4 C5 C6 -0.04(17) . . . . no
C4 C5 C6 C1 -0.32(15) . . . . no
C4 C5 C6 C7 -177.34(11) . . . . no
C1 C6 C7 O1 178.82(10) . . . . no
C1 C6 C7 C8 -0.05(12) . . . . no
C5 C6 C7 O1 -3.86(19) . . . . no
C5 C6 C7 C8 177.27(11) . . . . no
O1 C7 C8 N1 -176.43(9) . . . . no
O1 C7 C8 C9 -0.59(16) . . . . no
C6 C7 C8 N1 2.51(11) . . . . no
C6 C7 C8 C9 178.35(9) . . . . no
N1 C8 C9 N2 179.77(10) . . . . no
N1 C8 C9 C10 -0.12(17) . . . . no
C7 C8 C9 N2 4.62(16) . . . . no
C7 C8 C9 C10 -175.27(9) . . . . no
N2 C9 C10 O2 130.70(9) . . . . no
N2 C9 C10 O3 -110.95(9) . . . . no
N2 C9 C10 C11 7.80(10) . . . . no
C8 C9 C10 O2 -49.39(14) . . . . no
C8 C9 C10 O3 68.96(13) . . . . no
C8 C9 C10 C11 -172.29(10) . . . . no
O2 C10 C11 C12 51.38(15) . . . . no
O2 C10 C11 C16 -128.30(9) . . . . no
O3 C10 C11 C12 -68.72(15) . . . . no
O3 C10 C11 C16 111.60(10) . . . . no
C9 C10 C11 C12 173.06(11) . . . . no
C9 C10 C11 C16 -6.62(11) . . . . no
C10 C11 C12 C13 178.98(11) . . . . no
C16 C11 C12 C13 -1.37(16) . . . . no
C10 C11 C16 N2 3.37(12) . . . . no
C10 C11 C16 C15 -176.70(9) . . . . no
C12 C11 C16 N2 -176.35(10) . . . . no
C12 C11 C16 C15 3.58(16) . . . . no
C11 C12 C13 C14 -1.37(18) . . . . no
C12 C13 C14 C15 2.03(18) . . . . no
C13 C14 C15 C16 0.10(18) . . . . no
C14 C15 C16 N2 177.06(10) . . . . no
C14 C15 C16 C11 -2.87(16) . . . . no
N1 C17 C18 O2 72.48(11) . . . . no
N1 C17 C18 C19 -45.03(13) . . . . no
O2 C18 C19 O3 -16.27(11) . . . . no
C17 C18 C19 O3 106.27(11) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 2.8051(12) . . no
O1 C17 3.2800(13) . 2_666 no
O1 C13 3.4061(15) . 6_656 no
O2 C18 3.2284(13) . 7_655 no
O2 O2 3.1681(11) . 7_655 no
O2 N1 3.1012(12) . . no
N2 C4 3.4177(15) . 2_666 no
N2 C5 3.4019(14) . 2_666 no
N2 C2 3.3719(14) . 3_655 no
C3 C15 3.4294(16) . 2_666 no
C3 C16 3.5325(15) . 2_666 no
C4 C11 3.5618(15) . 2_666 no
C4 C4 3.5596(16) . 7_665 no
C4 C15 3.3883(16) . 2_666 no
C4 C16 3.1578(15) . 2_666 no
C5 C9 3.4074(15) . 2_666 no
C5 C16 3.5346(15) . 2_666 no
C6 C9 3.5220(14) . 2_666 no
C6 C8 3.5556(14) . 2_666 no
C7 C7 3.4556(14) . 2_666 no
C7 C8 3.4073(14) . 2_666 no
C8 C19 3.3955(15) . . no




_iucr_refine_instruction_details_constraints 
;
#
# Punched on 09/09/15 at 15:13:33
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT O    (    1 ,X'S,U'S)  UNTIL C    (   19 ) 
CONT H    (    2 ,X'S)  UNTIL H    (  192 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 09/09/15 at 15:13:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kel1608SN
_database_code_depnum_ccdc_archive 'CCDC 1590271'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             16-07-25
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1608SN\Tony_kel1608SN_data At 16:34 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   23.5193(13)
_cell_length_b                   11.6263(7)
_cell_length_c                   9.3856(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.966(5)
_cell_angle_gamma                90
_cell_volume                     2566.1(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 = C31 H25 N3 O4 S1 
# Dc =      1.39 Fooo =   1120.00 Mu =     14.82 M =    535.62
# Found Formula = C31 H25 N3 O4 S1 
# Dc =      1.39 FOOO =   1120.00 Mu =     14.82 M =    535.62

_chemical_formula_sum            'C31 H25 N3 O4 S'
_chemical_formula_moiety         'C31 H25 N3 O4 S'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         535.62


_cell_measurement_reflns_used    1769
_cell_measurement_theta_min      4
_cell_measurement_theta_max      71
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.014
_exptl_crystal_size_mid          0.031
_exptl_crystal_size_max          0.155

_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    1.482

# Sheldrick geometric approximatio 0.96 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro version 1.171.38.43 (Rigaku Oxford Diffraction, 2016)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.98
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
#_diffrn_ambient_temperature 150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'

_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    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            16907
_reflns_number_total             4953
_diffrn_reflns_av_R_equivalents  0.079
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4953 
# Theoretical number of reflections is about 10137 


_diffrn_reflns_theta_min         3.759
_diffrn_reflns_theta_max         72.273
_diffrn_measured_fraction_theta_max 0.975

_diffrn_reflns_theta_full        67.958
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -28
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   2.67
_oxford_diffrn_Wilson_scale      0.07

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

_refine_diff_density_min         -0.68
_refine_diff_density_max         0.61


# 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>-10.0\s(I)
_refine_ls_number_reflns         4953
_refine_ls_number_restraints     0
_refine_ls_number_parameters     352
_oxford_refine_ls_R_factor_ref   0.1170
_refine_ls_wR_factor_ref         0.1532
_refine_ls_goodness_of_fit_ref   1.0135
_refine_ls_shift/su_max          0.0001434
_refine_ls_shift/su_mean         0.0000139


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4953
_refine_ls_R_factor_all          0.1170
_refine_ls_wR_factor_all         0.1532

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3162
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_gt          0.1319

# 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 + 2.75P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               

The H atoms attached to C were included at calculated positions
and those bonded to N were located in 
a difference electron density map.
They were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98, N---H = 0.86 Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined with riding constraints
and the displacement parameters were held fixed. 

The largest peaks in the final difference electron density map
are located randomly through the structure.


;

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
S1 S 0.13604(4) 0.47365(10) 0.25274(10) 0.0377 1.0000 Uani . . . . . .
O1 O 0.28354(11) 0.1723(2) 0.6356(3) 0.0339 1.0000 Uani . . . . . .
O2 O 0.40012(11) 0.4607(3) 0.3171(3) 0.0406 1.0000 Uani . . . . . .
O3 O 0.12139(12) 0.3632(3) 0.1935(3) 0.0443 1.0000 Uani . . . . . .
O4 O 0.12503(12) 0.5751(3) 0.1691(3) 0.0465 1.0000 Uani . . . . . .
N1 N 0.28668(13) 0.4612(3) 0.5224(3) 0.0307 1.0000 Uani . . . . . .
N2 N 0.35751(13) 0.1862(3) 0.4229(3) 0.0312 1.0000 Uani . . . . . .
N3 N 0.20281(14) 0.4645(3) 0.3000(3) 0.0361 1.0000 Uani . . . . . .
C1 C 0.24846(15) 0.4659(4) 0.6356(4) 0.0316 1.0000 Uani . . . . . .
C2 C 0.21944(16) 0.5599(4) 0.6897(4) 0.0352 1.0000 Uani . . . . . .
C3 C 0.18527(16) 0.5421(4) 0.8069(4) 0.0383 1.0000 Uani . . . . . .
C4 C 0.18020(16) 0.4346(4) 0.8705(4) 0.0389 1.0000 Uani . . . . . .
C5 C 0.20843(16) 0.3413(4) 0.8159(4) 0.0358 1.0000 Uani . . . . . .
C6 C 0.24279(15) 0.3577(4) 0.6986(3) 0.0302 1.0000 Uani . . . . . .
C7 C 0.27713(15) 0.2774(3) 0.6187(4) 0.0292 1.0000 Uani . . . . . .
C8 C 0.30582(15) 0.3483(3) 0.5101(4) 0.0280 1.0000 Uani . . . . . .
C9 C 0.34763(15) 0.3032(3) 0.4262(4) 0.0278 1.0000 Uani . . . . . .
C10 C 0.39088(16) 0.3573(4) 0.3319(4) 0.0311 1.0000 Uani . . . . . .
C11 C 0.42236(15) 0.2612(4) 0.2710(4) 0.0302 1.0000 Uani . . . . . .
C12 C 0.46629(16) 0.2581(4) 0.1734(4) 0.0364 1.0000 Uani . . . . . .
C13 C 0.48943(17) 0.1520(4) 0.1400(4) 0.0427 1.0000 Uani . . . . . .
C14 C 0.46908(17) 0.0528(4) 0.2028(4) 0.0415 1.0000 Uani . . . . . .
C15 C 0.42492(17) 0.0534(4) 0.2992(4) 0.0385 1.0000 Uani . . . . . .
C16 C 0.40213(15) 0.1604(3) 0.3320(4) 0.0295 1.0000 Uani . . . . . .
C17 C 0.28864(15) 0.5514(3) 0.4127(4) 0.0303 1.0000 Uani . . . . . .
C18 C 0.23042(16) 0.5727(3) 0.3421(4) 0.0332 1.0000 Uani . . . . . .
C19 C 0.31503(16) 0.6608(4) 0.4727(4) 0.0329 1.0000 Uani . . . . . .
C20 C 0.36424(19) 0.6538(4) 0.5547(5) 0.0490 1.0000 Uani . . . . . .
C21 C 0.3898(2) 0.7518(5) 0.6097(5) 0.0601 1.0000 Uani . . . . . .
C22 C 0.3669(2) 0.8584(4) 0.5824(5) 0.0558 1.0000 Uani . . . . . .
C23 C 0.3180(2) 0.8664(4) 0.5029(6) 0.0594 1.0000 Uani . . . . . .
C24 C 0.2926(2) 0.7682(4) 0.4469(5) 0.0531 1.0000 Uani . . . . . .
C25 C 0.10252(16) 0.4914(4) 0.4168(4) 0.0390 1.0000 Uani . . . . . .
C26 C 0.09730(17) 0.3977(4) 0.5071(4) 0.0434 1.0000 Uani . . . . . .
C27 C 0.07118(18) 0.4117(5) 0.6377(5) 0.0537 1.0000 Uani . . . . . .
C28 C 0.05160(18) 0.5191(6) 0.6797(4) 0.0591 1.0000 Uani . . . . . .
C29 C 0.05728(19) 0.6111(5) 0.5888(5) 0.0593 1.0000 Uani . . . . . .
C30 C 0.08270(18) 0.5989(5) 0.4560(4) 0.0485 1.0000 Uani . . . . . .
C31 C 0.0254(2) 0.5335(6) 0.8250(5) 0.0812 1.0000 Uani . . . . . .
H2 H 0.3401 0.1376 0.4758 0.0372 1.0000 Uiso R . . . . .
H3 H 0.2227 0.4213 0.2453 0.0431 1.0000 Uiso R . . . . .
H21 H 0.2229 0.6329 0.6490 0.0417 1.0000 Uiso R . . . . .
H31 H 0.1650 0.6045 0.8443 0.0463 1.0000 Uiso R . . . . .
H41 H 0.1570 0.4267 0.9508 0.0469 1.0000 Uiso R . . . . .
H51 H 0.2040 0.2673 0.8558 0.0425 1.0000 Uiso R . . . . .
H121 H 0.4796 0.3261 0.1329 0.0438 1.0000 Uiso R . . . . .
H131 H 0.5193 0.1482 0.0747 0.0511 1.0000 Uiso R . . . . .
H141 H 0.4859 -0.0181 0.1809 0.0503 1.0000 Uiso R . . . . .
H151 H 0.4109 -0.0145 0.3379 0.0461 1.0000 Uiso R . . . . .
H171 H 0.3139 0.5229 0.3388 0.0356 1.0000 Uiso R . . . . .
H181 H 0.2057 0.6105 0.4103 0.0399 1.0000 Uiso R . . . . .
H182 H 0.2345 0.6224 0.2581 0.0400 1.0000 Uiso R . . . . .
H201 H 0.3801 0.5827 0.5742 0.0589 1.0000 Uiso R . . . . .
H211 H 0.4233 0.7451 0.6651 0.0717 1.0000 Uiso R . . . . .
H221 H 0.3845 0.9249 0.6191 0.0667 1.0000 Uiso R . . . . .
H231 H 0.3012 0.9381 0.4862 0.0714 1.0000 Uiso R . . . . .
H241 H 0.2592 0.7748 0.3917 0.0639 1.0000 Uiso R . . . . .
H261 H 0.1111 0.3252 0.4798 0.0520 1.0000 Uiso R . . . . .
H271 H 0.0667 0.3486 0.6977 0.0636 1.0000 Uiso R . . . . .
H291 H 0.0443 0.6848 0.6157 0.0707 1.0000 Uiso R . . . . .
H301 H 0.0870 0.6613 0.3965 0.0578 1.0000 Uiso R . . . . .
H311 H 0.0104 0.6100 0.8340 0.1219 1.0000 Uiso R . . . . .
H312 H -0.0049 0.4799 0.8367 0.1219 1.0000 Uiso R . . . . .
H313 H 0.0533 0.5207 0.8985 0.1218 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.01(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 . O3 . 1.439(3) yes
S1 . O4 . 1.438(3) yes
S1 . N3 . 1.628(3) yes
S1 . C25 . 1.754(4) yes
O1 . C7 . 1.241(5) yes
O2 . C10 . 1.229(5) yes
N1 . C1 . 1.405(4) yes
N1 . C8 . 1.393(5) yes
N1 . C17 . 1.471(5) yes
N2 . C9 . 1.380(5) yes
N2 . C16 . 1.396(4) yes
N2 . H2 . 0.861 no
N3 . C18 . 1.467(5) yes
N3 . H3 . 0.862 no
C1 . C2 . 1.389(5) yes
C1 . C6 . 1.397(5) yes
C2 . C3 . 1.388(5) yes
C2 . H21 . 0.935 no
C3 . C4 . 1.391(6) yes
C3 . H31 . 0.939 no
C4 . C5 . 1.375(6) yes
C4 . H41 . 0.943 no
C5 . C6 . 1.390(5) yes
C5 . H51 . 0.945 no
C6 . C7 . 1.452(5) yes
C7 . C8 . 1.482(5) yes
C8 . C9 . 1.374(5) yes
C9 . C10 . 1.498(5) yes
C10 . C11 . 1.462(5) yes
C11 . C12 . 1.393(5) yes
C11 . C16 . 1.392(5) yes
C12 . C13 . 1.386(6) yes
C12 . H121 . 0.934 no
C13 . C14 . 1.385(6) yes
C13 . H131 . 0.941 no
C14 . C15 . 1.388(5) yes
C14 . H141 . 0.938 no
C15 . C16 . 1.391(5) yes
C15 . H151 . 0.932 no
C17 . C18 . 1.531(5) yes
C17 . C19 . 1.520(5) yes
C17 . H171 . 0.978 no
C18 . H181 . 0.977 no
C18 . H182 . 0.983 no
C19 . C20 . 1.381(6) yes
C19 . C24 . 1.375(6) yes
C20 . C21 . 1.385(7) yes
C20 . H201 . 0.924 no
C21 . C22 . 1.374(7) yes
C21 . H211 . 0.939 no
C22 . C23 . 1.363(7) yes
C22 . H221 . 0.940 no
C23 . C24 . 1.388(7) yes
C23 . H231 . 0.934 no
C24 . H241 . 0.938 no
C25 . C26 . 1.388(6) yes
C25 . C30 . 1.386(6) yes
C26 . C27 . 1.390(5) yes
C26 . H261 . 0.939 no
C27 . C28 . 1.390(7) yes
C27 . H271 . 0.932 no
C28 . C29 . 1.377(8) yes
C28 . C31 . 1.515(5) yes
C29 . C30 . 1.398(5) yes
C29 . H291 . 0.946 no
C30 . H301 . 0.922 no
C31 . H311 . 0.961 no
C31 . H312 . 0.953 no
C31 . H313 . 0.956 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
O3 . S1 . O4 . 118.74(18) yes
O3 . S1 . N3 . 105.69(18) yes
O4 . S1 . N3 . 111.51(18) yes
O3 . S1 . C25 . 109.7(2) yes
O4 . S1 . C25 . 107.65(19) yes
N3 . S1 . C25 . 102.36(17) yes
C1 . N1 . C8 . 108.1(3) yes
C1 . N1 . C17 . 122.0(3) yes
C8 . N1 . C17 . 126.9(3) yes
C9 . N2 . C16 . 110.8(3) yes
C9 . N2 . H2 . 123.5 no
C16 . N2 . H2 . 125.5 no
S1 . N3 . C18 . 115.9(3) yes
S1 . N3 . H3 . 114.0 no
C18 . N3 . H3 . 114.7 no
N1 . C1 . C2 . 129.2(4) yes
N1 . C1 . C6 . 110.6(3) yes
C2 . C1 . C6 . 120.2(3) yes
C1 . C2 . C3 . 117.8(4) yes
C1 . C2 . H21 . 121.2 no
C3 . C2 . H21 . 120.9 no
C2 . C3 . C4 . 121.9(4) yes
C2 . C3 . H31 . 119.0 no
C4 . C3 . H31 . 119.1 no
C3 . C4 . C5 . 120.2(3) yes
C3 . C4 . H41 . 119.0 no
C5 . C4 . H41 . 120.7 no
C4 . C5 . C6 . 118.5(4) yes
C4 . C5 . H51 . 120.9 no
C6 . C5 . H51 . 120.6 no
C1 . C6 . C5 . 121.3(4) yes
C1 . C6 . C7 . 107.6(3) yes
C5 . C6 . C7 . 131.1(4) yes
C6 . C7 . O1 . 129.4(3) yes
C6 . C7 . C8 . 105.1(3) yes
O1 . C7 . C8 . 125.5(3) yes
C7 . C8 . N1 . 108.4(3) yes
C7 . C8 . C9 . 121.4(3) yes
N1 . C8 . C9 . 129.9(3) yes
N2 . C9 . C8 . 120.8(3) yes
N2 . C9 . C10 . 106.5(3) yes
C8 . C9 . C10 . 132.7(4) yes
C9 . C10 . O2 . 126.9(4) yes
C9 . C10 . C11 . 105.2(3) yes
O2 . C10 . C11 . 127.7(3) yes
C10 . C11 . C12 . 131.5(4) yes
C10 . C11 . C16 . 107.7(3) yes
C12 . C11 . C16 . 120.8(4) yes
C11 . C12 . C13 . 118.1(4) yes
C11 . C12 . H121 . 120.3 no
C13 . C12 . H121 . 121.7 no
C12 . C13 . C14 . 120.3(4) yes
C12 . C13 . H131 . 119.3 no
C14 . C13 . H131 . 120.3 no
C13 . C14 . C15 . 122.7(4) yes
C13 . C14 . H141 . 119.3 no
C15 . C14 . H141 . 118.0 no
C14 . C15 . C16 . 116.4(4) yes
C14 . C15 . H151 . 121.5 no
C16 . C15 . H151 . 122.1 no
N2 . C16 . C11 . 109.6(3) yes
N2 . C16 . C15 . 128.6(4) yes
C11 . C16 . C15 . 121.7(3) yes
N1 . C17 . C18 . 112.3(3) yes
N1 . C17 . C19 . 110.8(3) yes
C18 . C17 . C19 . 112.4(3) yes
N1 . C17 . H171 . 106.4 no
C18 . C17 . H171 . 107.3 no
C19 . C17 . H171 . 107.3 no
C17 . C18 . N3 . 111.5(3) yes
C17 . C18 . H181 . 109.1 no
N3 . C18 . H181 . 107.3 no
C17 . C18 . H182 . 110.1 no
N3 . C18 . H182 . 109.7 no
H181 . C18 . H182 . 109.1 no
C17 . C19 . C20 . 119.4(4) yes
C17 . C19 . C24 . 122.8(4) yes
C20 . C19 . C24 . 117.8(4) yes
C19 . C20 . C21 . 120.9(5) yes
C19 . C20 . H201 . 119.7 no
C21 . C20 . H201 . 119.4 no
C20 . C21 . C22 . 120.4(5) yes
C20 . C21 . H211 . 119.5 no
C22 . C21 . H211 . 120.1 no
C21 . C22 . C23 . 119.3(5) yes
C21 . C22 . H221 . 120.3 no
C23 . C22 . H221 . 120.5 no
C22 . C23 . C24 . 120.3(5) yes
C22 . C23 . H231 . 120.2 no
C24 . C23 . H231 . 119.5 no
C23 . C24 . C19 . 121.3(5) yes
C23 . C24 . H241 . 119.5 no
C19 . C24 . H241 . 119.2 no
S1 . C25 . C26 . 119.3(3) yes
S1 . C25 . C30 . 119.9(3) yes
C26 . C25 . C30 . 120.8(4) yes
C25 . C26 . C27 . 119.4(5) yes
C25 . C26 . H261 . 120.2 no
C27 . C26 . H261 . 120.3 no
C26 . C27 . C28 . 120.6(5) yes
C26 . C27 . H271 . 119.8 no
C28 . C27 . H271 . 119.6 no
C27 . C28 . C29 . 119.1(4) yes
C27 . C28 . C31 . 119.8(5) yes
C29 . C28 . C31 . 121.1(5) yes
C28 . C29 . C30 . 121.4(5) yes
C28 . C29 . H291 . 120.2 no
C30 . C29 . H291 . 118.4 no
C29 . C30 . C25 . 118.6(5) yes
C29 . C30 . H301 . 120.9 no
C25 . C30 . H301 . 120.5 no
C28 . C31 . H311 . 109.7 no
C28 . C31 . H312 . 110.3 no
H311 . C31 . H312 . 108.6 no
C28 . C31 . H313 . 110.3 no
H311 . C31 . H313 . 109.2 no
H312 . C31 . H313 . 108.7 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
N2 . H2 . O1 . 128 0.86 2.06 2.675(6) yes
N3 . H3 . O1 4_554 169 0.86 2.08 2.935(6) yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 S1 N3 C18 170.3(3) . . . . no
O4 S1 N3 C18 39.9(3) . . . . no
C25 S1 N3 C18 -75.0(3) . . . . no
O3 S1 C25 C26 37.4(4) . . . . no
O3 S1 C25 C30 -144.0(3) . . . . no
O4 S1 C25 C26 167.9(3) . . . . no
O4 S1 C25 C30 -13.5(4) . . . . no
N3 S1 C25 C26 -74.5(4) . . . . no
N3 S1 C25 C30 104.2(3) . . . . no
C8 N1 C1 C2 178.6(4) . . . . no
C8 N1 C1 C6 0.6(4) . . . . no
C17 N1 C1 C2 -19.8(6) . . . . no
C17 N1 C1 C6 162.2(3) . . . . no
C1 N1 C8 C7 1.5(4) . . . . no
C1 N1 C8 C9 -172.4(4) . . . . no
C17 N1 C8 C7 -159.0(3) . . . . no
C17 N1 C8 C9 27.2(6) . . . . no
C1 N1 C17 C18 -54.2(4) . . . . no
C1 N1 C17 C19 72.5(4) . . . . no
C8 N1 C17 C18 103.8(4) . . . . no
C8 N1 C17 C19 -129.5(4) . . . . no
C16 N2 C9 C8 -179.4(3) . . . . no
C16 N2 C9 C10 -1.6(4) . . . . no
C9 N2 C16 C11 -0.9(4) . . . . no
C9 N2 C16 C15 -179.8(4) . . . . no
S1 N3 C18 C17 168.4(2) . . . . no
N1 C1 C2 C3 -177.7(4) . . . . no
C6 C1 C2 C3 0.1(5) . . . . no
N1 C1 C6 C5 178.1(3) . . . . no
N1 C1 C6 C7 -2.5(4) . . . . no
C2 C1 C6 C5 -0.1(5) . . . . no
C2 C1 C6 C7 179.3(3) . . . . no
C1 C2 C3 C4 0.7(6) . . . . no
C2 C3 C4 C5 -1.5(6) . . . . no
C3 C4 C5 C6 1.4(6) . . . . no
C4 C5 C6 C1 -0.6(5) . . . . no
C4 C5 C6 C7 -179.9(4) . . . . no
C1 C6 C7 O1 -178.3(4) . . . . no
C1 C6 C7 C8 3.3(4) . . . . no
C5 C6 C7 O1 1.0(7) . . . . no
C5 C6 C7 C8 -177.4(4) . . . . no
O1 C7 C8 N1 178.6(3) . . . . no
O1 C7 C8 C9 -6.9(6) . . . . no
C6 C7 C8 N1 -2.9(4) . . . . no
C6 C7 C8 C9 171.6(3) . . . . no
N1 C8 C9 N2 -175.6(3) . . . . no
N1 C8 C9 C10 7.4(7) . . . . no
C7 C8 C9 N2 11.2(5) . . . . no
C7 C8 C9 C10 -165.8(4) . . . . no
N2 C9 C10 O2 -172.3(4) . . . . no
N2 C9 C10 C11 3.4(4) . . . . no
C8 C9 C10 O2 5.1(7) . . . . no
C8 C9 C10 C11 -179.3(4) . . . . no
O2 C10 C11 C12 -6.5(7) . . . . no
O2 C10 C11 C16 171.7(4) . . . . no
C9 C10 C11 C12 178.0(4) . . . . no
C9 C10 C11 C16 -3.9(4) . . . . no
C10 C11 C12 C13 177.4(4) . . . . no
C16 C11 C12 C13 -0.5(6) . . . . no
C10 C11 C16 N2 3.0(4) . . . . no
C10 C11 C16 C15 -178.0(3) . . . . no
C12 C11 C16 N2 -178.6(3) . . . . no
C12 C11 C16 C15 0.4(6) . . . . no
C11 C12 C13 C14 -0.1(6) . . . . no
C12 C13 C14 C15 0.8(6) . . . . no
C13 C14 C15 C16 -0.9(6) . . . . no
C14 C15 C16 N2 179.1(4) . . . . no
C14 C15 C16 C11 0.3(6) . . . . no
N1 C17 C18 N3 -47.5(4) . . . . no
C19 C17 C18 N3 -173.3(3) . . . . no
N1 C17 C19 C20 45.6(5) . . . . no
N1 C17 C19 C24 -135.6(4) . . . . no
C18 C17 C19 C20 172.2(4) . . . . no
C18 C17 C19 C24 -9.0(5) . . . . no
C17 C19 C20 C21 179.3(4) . . . . no
C24 C19 C20 C21 0.4(6) . . . . no
C17 C19 C24 C23 -179.7(4) . . . . no
C20 C19 C24 C23 -0.9(7) . . . . no
C19 C20 C21 C22 -0.7(7) . . . . no
C20 C21 C22 C23 1.4(7) . . . . no
C21 C22 C23 C24 -1.8(8) . . . . no
C22 C23 C24 C19 1.6(8) . . . . no
S1 C25 C26 C27 179.5(3) . . . . no
C30 C25 C26 C27 0.9(6) . . . . no
S1 C25 C30 C29 -178.6(3) . . . . no
C26 C25 C30 C29 0.0(6) . . . . no
C25 C26 C27 C28 -1.6(6) . . . . no
C26 C27 C28 C29 1.4(7) . . . . no
C26 C27 C28 C31 -177.5(4) . . . . no
C27 C28 C29 C30 -0.5(7) . . . . no
C31 C28 C29 C30 178.4(4) . . . . no
C28 C29 C30 C25 -0.2(7) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 2.675(4) . . no
O1 C10 3.119(5) . 4_555 no
O1 N3 2.935(4) . 4_555 no
O1 C9 3.107(5) . 4_555 no
O2 C20 3.285(6) . . no
O2 C14 3.266(5) . 3_655 no
O2 C17 2.978(4) . . no
O2 C19 3.413(5) . . no
O2 C22 3.135(6) . 4_564 no
O3 C5 3.329(5) . 4_554 no
N1 N3 2.848(4) . . no
N2 C7 3.424(5) . 4_554 no
N2 C6 3.432(4) . 4_554 no
N3 C1 3.311(5) . . no
N3 C8 3.380(5) . . no
C1 C20 3.582(6) . . no
C2 C18 3.280(5) . . no
C2 C19 3.276(5) . . no
C2 C24 3.556(6) . 4_565 no
C3 C28 3.355(6) . . no
C3 C27 3.446(6) . . no
C3 C24 3.585(6) . 4_565 no
C4 C27 3.351(6) . . no
C5 C7 3.527(5) . 4_555 no
C7 C9 3.435(5) . 4_555 no
C10 C17 3.393(5) . . no
C31 C31 3.600(7) . 2_567 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 25/07/16 at 17:17:33
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE N   (   2,X'S) H   (   2,X'S) 
RIDE N   (   3,X'S) H   (   3,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) H   ( 182,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  27,X'S) H   ( 271,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) 
RIDE C   (  31,X'S) H   ( 311,X'S) H   ( 312,X'S) H   ( 313,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 25/07/16 at 17:17:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kel1602SNM
_database_code_depnum_ccdc_archive 'CCDC 1590269'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             16-03-02
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1602SNM\Tony_kel1602SNM_da At 12: 1 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   23.9584(7)
_cell_length_b                   9.6484(3)
_cell_length_c                   16.0090(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.165(3)
_cell_angle_gamma                90
_cell_volume                     3700.6(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1 '
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,z
-x+1/2,-y+1/2,-z
-x,y,-z+1/2
x,-y,z+1/2
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

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


_cell_formula_units_Z            8

# Given Formula = C22 H18 N2 O4 
# Dc =      1.34 Fooo =   1744.00 Mu =      0.94 M =    374.40
# Found Formula = C23 H18 N2 O6 
# Dc =      1.50 FOOO =   1744.00 Mu =      1.10 M =    418.41

_chemical_formula_sum            'C23 H18 N2 O6'
_chemical_formula_moiety         'C23 H18 N2 O6'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         418.41


_cell_measurement_reflns_used    15550
_cell_measurement_theta_min      2
_cell_measurement_theta_max      29
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.035
_exptl_crystal_size_mid          0.258
_exptl_crystal_size_max          0.444

_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1744
_exptl_absorpt_coefficient_mu    0.110

# Sheldrick geometric approximatio 0.97 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  1.00
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2' ####
_diffrn_radiation_source         
'Supermova (Mo) X-ray Source' ################
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  mirror
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_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    'PLATON (Spek, 2008)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            39146
_reflns_number_total             4736
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 4736 
# Theoretical number of reflections is about 10182 


_diffrn_reflns_theta_min         2.276
_diffrn_reflns_theta_max         29.364
_diffrn_measured_fraction_theta_max 0.931

_diffrn_reflns_theta_full        27.572
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_reflns_limit_h_min              -32
_reflns_limit_h_max              32
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              21

_oxford_diffrn_Wilson_B_factor   1.85
_oxford_diffrn_Wilson_scale      0.50

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

_refine_diff_density_min         -0.20
_refine_diff_density_max         0.26


# 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>-10.0\s(I)
_refine_ls_number_reflns         4734
_refine_ls_number_restraints     0
_refine_ls_number_parameters     281
_oxford_refine_ls_R_factor_ref   0.0474
_refine_ls_wR_factor_ref         0.1093
_refine_ls_goodness_of_fit_ref   1.0328
_refine_ls_shift/su_max          0.0019217
_refine_ls_shift/su_mean         0.0004532


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        4734
_refine_ls_R_factor_all          0.0474
_refine_ls_wR_factor_all         0.1093

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4495
_refine_ls_R_factor_gt           0.0443
_refine_ls_wR_factor_gt          0.1074

# 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 + 4.28P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
Initially the crystal system appeared to be orthorhombic 
but the software program SUPERFLIP identified that it was actually monoclinic. 
Intensity data were extracted from the CCD frames on this basis.
The structure was solved and refined 
assuming that there was no twinning, and yielded 
an R-factor for a model with isotropic displacement parameters,
using unit weights, of 0.305.
A possible twin rule was identified using ROTAX within CRYSTALS
(a rotation of 180° about direct lattice vector 1 0 0),
 and, when this twinning was included in the 
refinement, the R-factor lowered to 0.141 for the same stage of refinement.
From there the refinement proceeded very smoothly
by routine procedures.
The final twin ratio was 0.585:0.415(1) 



The H atoms were all located in a difference electron density map, but 
were repositioned geometrically. 
The H atoms were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined with riding constraints
and the displacement parameters were held fixed. 

The largest peaks in the final difference electron density map
are located midway between bonded atoms.


;

# 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 0.30775(6) 0.37246(14) 0.38227(11) 0.0261 1.0000 Uani . . . . . .
O2 O 0.36688(5) 0.91491(14) 0.41143(9) 0.0194 1.0000 Uani . . . . . .
O3 O 0.36726(6) 0.84172(14) 0.27673(9) 0.0215 1.0000 Uani . . . . . .
O4 O 0.14114(5) 0.52449(13) 0.38497(9) 0.0217 1.0000 Uani . . . . . .
O5 O 0.13136(6) 0.31618(15) 0.44227(10) 0.0274 1.0000 Uani . . . . . .
O6 O 0.05589(6) 0.43044(17) 0.39574(12) 0.0358 1.0000 Uani . . . . . .
N1 N 0.41628(6) 0.62321(17) 0.38681(12) 0.0239 1.0000 Uani . . . . . .
N2 N 0.26237(6) 0.68356(15) 0.38433(10) 0.0170 1.0000 Uani . . . . . .
C1 C 0.35830(7) 0.59218(19) 0.39013(13) 0.0201 1.0000 Uani . . . . . .
C2 C 0.35128(8) 0.43874(19) 0.38461(13) 0.0206 1.0000 Uani . . . . . .
C3 C 0.40853(7) 0.3863(2) 0.37586(14) 0.0220 1.0000 Uani . . . . . .
C4 C 0.42738(8) 0.2516(2) 0.36489(14) 0.0263 1.0000 Uani . . . . . .
C5 C 0.48407(9) 0.2303(2) 0.35634(16) 0.0305 1.0000 Uani . . . . . .
C6 C 0.52077(8) 0.3428(2) 0.35926(16) 0.0320 1.0000 Uani . . . . . .
C7 C 0.50265(8) 0.4780(2) 0.37191(16) 0.0308 1.0000 Uani . . . . . .
C8 C 0.44518(7) 0.4985(2) 0.37937(14) 0.0225 1.0000 Uani . . . . . .
C9 C 0.31969(7) 0.69355(18) 0.37867(12) 0.0179 1.0000 Uani . . . . . .
C10 C 0.33500(7) 0.84268(19) 0.35077(12) 0.0168 1.0000 Uani . . . . . .
C11 C 0.27851(7) 0.90693(19) 0.33930(12) 0.0176 1.0000 Uani . . . . . .
C12 C 0.26442(8) 1.04175(19) 0.31749(12) 0.0210 1.0000 Uani . . . . . .
C13 C 0.20833(9) 1.0774(2) 0.31554(13) 0.0247 1.0000 Uani . . . . . .
C14 C 0.16785(8) 0.9802(2) 0.33573(14) 0.0275 1.0000 Uani . . . . . .
C15 C 0.18161(8) 0.8447(2) 0.35859(14) 0.0248 1.0000 Uani . . . . . .
C16 C 0.23762(7) 0.81048(19) 0.36032(12) 0.0181 1.0000 Uani . . . . . .
C17 C 0.44028(8) 0.7412(2) 0.43167(14) 0.0249 1.0000 Uani . . . . . .
C18 C 0.42429(8) 0.8799(2) 0.39324(13) 0.0218 1.0000 Uani . . . . . .
C19 C 0.42397(8) 0.8782(2) 0.29856(14) 0.0242 1.0000 Uani . . . . . .
C20 C 0.23363(7) 0.58797(19) 0.44025(12) 0.0174 1.0000 Uani . . . . . .
C21 C 0.19846(7) 0.47553(19) 0.39866(12) 0.0176 1.0000 Uani . . . . . .
C22 C 0.18921(8) 0.35123(19) 0.45621(13) 0.0209 1.0000 Uani . . . . . .
C23 C 0.10519(8) 0.4244(2) 0.40692(13) 0.0243 1.0000 Uani . . . . . .
H41 H 0.4023 0.1751 0.3637 0.0314 1.0000 Uiso R . . . . .
H51 H 0.4993 0.1402 0.3490 0.0372 1.0000 Uiso R . . . . .
H61 H 0.5596 0.3259 0.3525 0.0378 1.0000 Uiso R . . . . .
H71 H 0.5287 0.5509 0.3757 0.0366 1.0000 Uiso R . . . . .
H121 H 0.2918 1.1069 0.3048 0.0248 1.0000 Uiso R . . . . .
H131 H 0.1974 1.1689 0.3001 0.0288 1.0000 Uiso R . . . . .
H141 H 0.1304 1.0076 0.3323 0.0330 1.0000 Uiso R . . . . .
H151 H 0.1540 0.7800 0.3712 0.0295 1.0000 Uiso R . . . . .
H171 H 0.4811 0.7341 0.4275 0.0296 1.0000 Uiso R . . . . .
H172 H 0.4286 0.7395 0.4907 0.0292 1.0000 Uiso R . . . . .
H181 H 0.4466 0.9522 0.4158 0.0251 1.0000 Uiso R . . . . .
H191 H 0.4325 0.9693 0.2767 0.0281 1.0000 Uiso R . . . . .
H192 H 0.4481 0.8091 0.2762 0.0283 1.0000 Uiso R . . . . .
H201 H 0.2620 0.5428 0.4741 0.0197 1.0000 Uiso R . . . . .
H202 H 0.2092 0.6432 0.4771 0.0209 1.0000 Uiso R . . . . .
H211 H 0.2142 0.4493 0.3461 0.0217 1.0000 Uiso R . . . . .
H221 H 0.1937 0.3769 0.5146 0.0247 1.0000 Uiso R . . . . .
H222 H 0.2129 0.2734 0.4409 0.0254 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.325(6)

loop_
_oxford_twin_element_scale_factors
0.5851(12)
0.4149(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.224(2) yes
O2 . C10 . 1.417(2) yes
O2 . C18 . 1.447(2) yes
O3 . C10 . 1.417(2) yes
O3 . C19 . 1.445(2) yes
O4 . C21 . 1.468(2) yes
O4 . C23 . 1.342(2) yes
O5 . C22 . 1.443(2) yes
O5 . C23 . 1.342(3) yes
O6 . C23 . 1.195(2) yes
N1 . C1 . 1.422(2) yes
N1 . C8 . 1.394(2) yes
N1 . C17 . 1.463(3) yes
N2 . C9 . 1.380(2) yes
N2 . C16 . 1.413(2) yes
N2 . C20 . 1.459(2) yes
C1 . C2 . 1.493(3) yes
C1 . C9 . 1.358(2) yes
C2 . C3 . 1.469(2) yes
C3 . C4 . 1.387(3) yes
C3 . C8 . 1.394(3) yes
C4 . C5 . 1.381(3) yes
C4 . H41 . 0.951 no
C5 . C6 . 1.397(3) yes
C5 . H51 . 0.950 no
C6 . C7 . 1.390(3) yes
C6 . H61 . 0.950 no
C7 . C8 . 1.396(2) yes
C7 . H71 . 0.941 no
C9 . C10 . 1.551(2) yes
C10 . C11 . 1.499(2) yes
C11 . C12 . 1.388(3) yes
C11 . C16 . 1.393(3) yes
C12 . C13 . 1.387(3) yes
C12 . H121 . 0.931 no
C13 . C14 . 1.388(3) yes
C13 . H131 . 0.953 no
C14 . C15 . 1.397(3) yes
C14 . H141 . 0.936 no
C15 . C16 . 1.382(3) yes
C15 . H151 . 0.931 no
C17 . C18 . 1.522(3) yes
C17 . H171 . 0.982 no
C17 . H172 . 0.987 no
C18 . C19 . 1.516(3) yes
C18 . H181 . 0.949 no
C19 . H191 . 0.968 no
C19 . H192 . 0.952 no
C20 . C21 . 1.525(2) yes
C20 . H201 . 0.971 no
C20 . H202 . 0.989 no
C21 . C22 . 1.529(3) yes
C21 . H211 . 0.957 no
C22 . H221 . 0.973 no
C22 . H222 . 0.973 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
C10 . O2 . C18 . 104.97(14) yes
C10 . O3 . C19 . 108.11(14) yes
C21 . O4 . C23 . 109.28(14) yes
C22 . O5 . C23 . 109.28(15) yes
C1 . N1 . C8 . 107.88(15) yes
C1 . N1 . C17 . 121.88(17) yes
C8 . N1 . C17 . 121.27(16) yes
C9 . N2 . C16 . 109.78(14) yes
C9 . N2 . C20 . 123.77(15) yes
C16 . N2 . C20 . 121.07(14) yes
N1 . C1 . C2 . 108.45(15) yes
N1 . C1 . C9 . 120.55(16) yes
C2 . C1 . C9 . 129.02(17) yes
C1 . C2 . O1 . 128.02(17) yes
C1 . C2 . C3 . 104.00(15) yes
O1 . C2 . C3 . 127.82(17) yes
C2 . C3 . C4 . 129.71(17) yes
C2 . C3 . C8 . 108.49(16) yes
C4 . C3 . C8 . 121.80(17) yes
C3 . C4 . C5 . 118.21(19) yes
C3 . C4 . H41 . 121.6 no
C5 . C4 . H41 . 120.2 no
C4 . C5 . C6 . 119.99(19) yes
C4 . C5 . H51 . 121.8 no
C6 . C5 . H51 . 118.2 no
C5 . C6 . C7 . 122.48(18) yes
C5 . C6 . H61 . 118.6 no
C7 . C6 . H61 . 118.9 no
C6 . C7 . C8 . 116.99(19) yes
C6 . C7 . H71 . 120.2 no
C8 . C7 . H71 . 122.8 no
C7 . C8 . C3 . 120.50(19) yes
C7 . C8 . N1 . 128.30(18) yes
C3 . C8 . N1 . 111.13(15) yes
N2 . C9 . C1 . 128.19(16) yes
N2 . C9 . C10 . 108.66(14) yes
C1 . C9 . C10 . 123.06(15) yes
C9 . C10 . O2 . 112.73(15) yes
C9 . C10 . O3 . 111.40(14) yes
O2 . C10 . O3 . 106.39(13) yes
C9 . C10 . C11 . 101.81(14) yes
O2 . C10 . C11 . 111.41(14) yes
O3 . C10 . C11 . 113.25(15) yes
C10 . C11 . C12 . 129.56(17) yes
C10 . C11 . C16 . 109.23(16) yes
C12 . C11 . C16 . 121.06(17) yes
C11 . C12 . C13 . 118.21(18) yes
C11 . C12 . H121 . 121.1 no
C13 . C12 . H121 . 120.7 no
C12 . C13 . C14 . 120.31(19) yes
C12 . C13 . H131 . 120.0 no
C14 . C13 . H131 . 119.7 no
C13 . C14 . C15 . 121.93(18) yes
C13 . C14 . H141 . 117.7 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . C16 . 117.19(18) yes
C14 . C15 . H151 . 121.1 no
C16 . C15 . H151 . 121.7 no
N2 . C16 . C11 . 110.47(15) yes
N2 . C16 . C15 . 128.23(17) yes
C11 . C16 . C15 . 121.27(17) yes
N1 . C17 . C18 . 112.83(17) yes
N1 . C17 . H171 . 107.6 no
C18 . C17 . H171 . 106.4 no
N1 . C17 . H172 . 110.2 no
C18 . C17 . H172 . 109.2 no
H171 . C17 . H172 . 110.5 no
C17 . C18 . O2 . 111.23(16) yes
C17 . C18 . C19 . 113.25(17) yes
O2 . C18 . C19 . 101.63(15) yes
C17 . C18 . H181 . 110.6 no
O2 . C18 . H181 . 106.7 no
C19 . C18 . H181 . 112.9 no
C18 . C19 . O3 . 104.28(15) yes
C18 . C19 . H191 . 110.6 no
O3 . C19 . H191 . 109.4 no
C18 . C19 . H192 . 112.5 no
O3 . C19 . H192 . 108.0 no
H191 . C19 . H192 . 111.7 no
N2 . C20 . C21 . 116.28(15) yes
N2 . C20 . H201 . 107.2 no
C21 . C20 . H201 . 108.0 no
N2 . C20 . H202 . 107.9 no
C21 . C20 . H202 . 108.4 no
H201 . C20 . H202 . 108.9 no
C20 . C21 . O4 . 110.58(14) yes
C20 . C21 . C22 . 112.07(15) yes
O4 . C21 . C22 . 101.84(13) yes
C20 . C21 . H211 . 110.7 no
O4 . C21 . H211 . 108.9 no
C22 . C21 . H211 . 112.4 no
C21 . C22 . O5 . 103.39(14) yes
C21 . C22 . H221 . 111.3 no
O5 . C22 . H221 . 108.2 no
C21 . C22 . H222 . 111.6 no
O5 . C22 . H222 . 109.9 no
H221 . C22 . H222 . 112.0 no
O5 . C23 . O4 . 111.77(16) yes
O5 . C23 . O6 . 124.15(19) yes
O4 . C23 . O6 . 124.08(19) yes


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O2 C10 O3 -34.48(18) . . . . no
C18 O2 C10 C9 87.90(17) . . . . no
C18 O2 C10 C11 -158.35(15) . . . . no
C10 O2 C18 C17 -82.70(19) . . . . no
C10 O2 C18 C19 38.18(17) . . . . no
C19 O3 C10 O2 15.74(18) . . . . no
C19 O3 C10 C9 -107.48(16) . . . . no
C19 O3 C10 C11 138.47(15) . . . . no
C10 O3 C19 C18 8.12(18) . . . . no
C23 O4 C21 C20 -136.01(16) . . . . no
C23 O4 C21 C22 -16.75(19) . . . . no
C21 O4 C23 O5 6.2(2) . . . . no
C21 O4 C23 O6 -173.2(2) . . . . no
C23 O5 C22 C21 -18.2(2) . . . . no
C22 O5 C23 O4 8.2(2) . . . . no
C22 O5 C23 O6 -172.3(2) . . . . no
C8 N1 C1 C2 0.2(2) . . . . no
C8 N1 C1 C9 -165.23(19) . . . . no
C17 N1 C1 C2 -147.30(18) . . . . no
C17 N1 C1 C9 47.3(3) . . . . no
C1 N1 C8 C3 1.3(3) . . . . no
C1 N1 C8 C7 178.3(2) . . . . no
C17 N1 C8 C3 148.95(19) . . . . no
C17 N1 C8 C7 -34.0(3) . . . . no
C1 N1 C17 C18 -71.4(2) . . . . no
C8 N1 C17 C18 145.37(19) . . . . no
C16 N2 C9 C1 -174.7(2) . . . . no
C16 N2 C9 C10 1.9(2) . . . . no
C20 N2 C9 C1 31.1(3) . . . . no
C20 N2 C9 C10 -152.34(16) . . . . no
C9 N2 C16 C11 -0.7(2) . . . . no
C9 N2 C16 C15 -178.7(2) . . . . no
C20 N2 C16 C11 154.32(17) . . . . no
C20 N2 C16 C15 -23.7(3) . . . . no
C9 N2 C20 C21 -115.72(19) . . . . no
C16 N2 C20 C21 92.9(2) . . . . no
N1 C1 C2 O1 -177.0(2) . . . . no
N1 C1 C2 C3 -1.4(2) . . . . no
C9 C1 C2 O1 -13.3(4) . . . . no
C9 C1 C2 C3 162.4(2) . . . . no
N1 C1 C9 N2 -176.09(19) . . . . no
N1 C1 C9 C10 7.8(3) . . . . no
C2 C1 C9 N2 21.9(4) . . . . no
C2 C1 C9 C10 -154.2(2) . . . . no
O1 C2 C3 C4 -1.6(4) . . . . no
O1 C2 C3 C8 177.8(2) . . . . no
C1 C2 C3 C4 -177.2(2) . . . . no
C1 C2 C3 C8 2.1(2) . . . . no
C2 C3 C4 C5 178.5(2) . . . . no
C8 C3 C4 C5 -0.8(3) . . . . no
C2 C3 C8 N1 -2.2(3) . . . . no
C2 C3 C8 C7 -179.5(2) . . . . no
C4 C3 C8 N1 177.2(2) . . . . no
C4 C3 C8 C7 -0.1(4) . . . . no
C3 C4 C5 C6 0.3(4) . . . . no
C4 C5 C6 C7 1.0(4) . . . . no
C5 C6 C7 C8 -1.8(4) . . . . no
C6 C7 C8 N1 -175.5(2) . . . . no
C6 C7 C8 C3 1.3(3) . . . . no
N2 C9 C10 O2 117.26(16) . . . . no
N2 C9 C10 O3 -123.21(16) . . . . no
N2 C9 C10 C11 -2.2(2) . . . . no
C1 C9 C10 O2 -66.0(2) . . . . no
C1 C9 C10 O3 53.6(2) . . . . no
C1 C9 C10 C11 174.54(19) . . . . no
O2 C10 C11 C12 57.0(3) . . . . no
O2 C10 C11 C16 -118.60(17) . . . . no
O3 C10 C11 C12 -62.9(3) . . . . no
O3 C10 C11 C16 121.51(17) . . . . no
C9 C10 C11 C12 177.4(2) . . . . no
C9 C10 C11 C16 1.8(2) . . . . no
C10 C11 C12 C13 -176.41(19) . . . . no
C16 C11 C12 C13 -1.3(3) . . . . no
C10 C11 C16 N2 -0.8(2) . . . . no
C10 C11 C16 C15 177.36(18) . . . . no
C12 C11 C16 N2 -176.88(17) . . . . no
C12 C11 C16 C15 1.3(3) . . . . no
C11 C12 C13 C14 0.6(3) . . . . no
C12 C13 C14 C15 0.1(3) . . . . no
C13 C14 C15 C16 -0.1(3) . . . . no
C14 C15 C16 N2 177.22(19) . . . . no
C14 C15 C16 C11 -0.6(3) . . . . no
N1 C17 C18 O2 74.3(2) . . . . no
N1 C17 C18 C19 -39.5(2) . . . . no
O2 C18 C19 O3 -28.05(17) . . . . no
C17 C18 C19 O3 91.39(18) . . . . no
N2 C20 C21 O4 -89.47(18) . . . . no
N2 C20 C21 C22 157.65(15) . . . . no
O4 C21 C22 O5 20.38(18) . . . . no
C20 C21 C22 O5 138.58(15) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 3.193(2) . . no
O1 C20 2.889(2) . . no
O1 C21 2.814(2) . . no
O1 C22 3.087(2) . . no
O1 C22 3.369(3) . 4_556 no
O2 C23 3.361(2) . 4_566 no
O2 C22 3.377(2) . 4_566 no
O2 N1 3.079(2) . . no
O2 C20 3.387(2) . 4_566 no
O3 C23 3.119(3) . 7_555 no
O3 O4 3.138(2) . 7_555 no
O3 N1 2.986(2) . . no
O4 O5 2.222(2) . . no
O4 C15 3.266(2) . . no
O6 C19 3.189(3) . 7_545 no
O6 C17 3.368(2) . 3_445 no
O6 C18 3.191(2) . 3_445 no
N2 C13 3.434(3) . 7_545 no
C1 C19 3.501(3) . . no
C2 C14 3.578(3) . 7_545 no
C2 C20 3.290(3) . . no
C5 C5 3.492(4) . 5_655 no
C6 C17 3.565(3) . 2_666 no
C9 C13 3.371(3) . 7_545 no
C11 C20 3.542(3) . 4_566 no
C13 C22 3.503(3) . 1_565 no
C16 C20 3.408(3) . 4_566 no
C19 C23 3.390(3) . 7_555 no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C20 H201 O1 0.97 2.46 2.889(2) 106. . yes
C21 H211 O1 0.96 2.43 2.814(2) 104. . yes



_iucr_refine_instruction_details_constraints 
;
#
# Punched on 02/03/16 at 12:35:14
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
SUMFIX ELEMENT SCALES 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
END                                                                             
;

_iucr_refine_instruction_details_restraints 
;
#
# Punched on 02/03/16 at 12:35:14
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
# Manually omitted reflections
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 14 x .
0 0 16 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kel1611SNQ
_database_code_depnum_ccdc_archive 'CCDC 1590270'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             16-10-20
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1611SNQ\Tony_kel1611SNQ_da At 12:23 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   10.5565(2)
_cell_length_b                   14.9406(2)
_cell_length_c                   25.9563(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4093.84(11)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 '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 # 8

# Given Formula = C21 H18 Cl2 N2 O4 
# Dc =      1.41 Fooo =   1801.26 Mu =     31.15 M =    866.58
# Found Formula = C21.00 H17.92 Cl2.07 N2 O4 
# Dc =      1.41 FOOO =   1801.26 Mu =     32.05 M =    871.59

_chemical_formula_sum            'C42 H35.85 Cl4.15 N4 O8'
_chemical_formula_moiety         
'2(C20 H16 N2 O4), 1.85(C H2 Cl2), 0.15(C H Cl3)'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         871.73


_cell_measurement_reflns_used    11874
_cell_measurement_theta_min      3
_cell_measurement_theta_max      64
_cell_measurement_temperature    150

_exptl_crystal_description       lath
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.018
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_max          0.257

_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             1801.264
_exptl_absorpt_coefficient_mu    3.205

# Sheldrick geometric approximatio 0.81 0.94 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro version 1.171.38.43 (Rigaku Oxford Diffraction, 2016)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.94
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.01(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'

_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    'PLATON (Spek, 2008)'
_diffrn_reflns_av_sigmaI/netI    0.0767

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

#_diffrn_ambient_temperature        150
_diffrn_reflns_number            61022
_reflns_number_total             7974
_diffrn_reflns_av_R_equivalents  0.056
# Number of reflections without Friedels Law is 7974 
# Number of reflections with Friedels Law is 4476 
# Theoretical number of reflections is about 4021 


_diffrn_reflns_theta_min         3.405
_diffrn_reflns_theta_max         71.949
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        71.949
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_reflns_limit_h_min              -12
_reflns_limit_h_max              13
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              31

_oxford_diffrn_Wilson_B_factor   4.29
_oxford_diffrn_Wilson_scale      0.13

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

_refine_diff_density_min         -0.40
_refine_diff_density_max         0.53


# 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>-10.0\s(I)
_refine_ls_number_reflns         7971
_refine_ls_number_restraints     66
_refine_ls_number_parameters     581
_oxford_refine_ls_R_factor_ref   0.0769
_refine_ls_wR_factor_ref         0.1506
_refine_ls_goodness_of_fit_ref   0.9821
_refine_ls_shift/su_max          0.0028496
_refine_ls_shift/su_mean         0.0001198


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        7971
_refine_ls_R_factor_all          0.0769
_refine_ls_wR_factor_all         0.1506

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                6934
_refine_ls_R_factor_gt           0.0684
_refine_ls_wR_factor_gt          0.1456

_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_abs_structure_details 'Flack (1983), 3498 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #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: 
 0.156E+04 0.244E+04 0.141E+04 512. 46.6 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               
Besides two C₂₀H₁₆N₂O₄ molecules, there were also two regions of solvate
molecules.  One region was clearly a dichloromethane molecule.
The other was less clearly defined and has been modelled as overlapping
images of two orientations of dichloromethane 
and one of chloroform, with their occupancies summing to 1.0.
Restraints were applied to distances, angles, displacement parameters
and occupancies, as appropriate.



Hydrogen atoms of the C₂₀H₁₆N₂O₄ molecules 
and non-disordered dichloromethane molecule
 were observed in difference electron density maps
prior to their inclusion.
Those bonded to C  were included at calculated positions
and initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å, 
N---H = 0.86Å, O---H = 0.83Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined with riding constraints
and the displacement parameters were held fixed. 
The H attached to O4 appeared to have refined to an unreasonable position
so was moved to a calculate location consistent with
H-bonding to O8 of an adjacent molecule.


The largest peaks in the final difference electron density map
are located adjacent to the region of disordered solvent molecules.





;

# 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
Cl1 Cl 0.69225(17) 0.35324(14) 0.67716(7) 0.0873 1.0000 Uani . . . . . .
Cl2 Cl 0.81215(17) 0.52883(12) 0.67613(6) 0.0768 1.0000 Uani . . . . . .
Cl11 Cl 0.5001(3) 0.4464(2) 0.89283(11) 0.0860 0.439(5) Uani D U P . . .
Cl12 Cl 0.4847(5) 0.4186(5) 0.78258(17) 0.1129 0.439(5) Uani D U P . . .
Cl21 Cl 0.5001(3) 0.4464(2) 0.89283(11) 0.0860 0.150(6) Uani D U P . . .
Cl22 Cl 0.4036(17) 0.3371(12) 0.8122(5) 0.1274 0.150(6) Uani D U P . . .
Cl23 Cl 0.5150(19) 0.5018(14) 0.7883(6) 0.1282 0.150(6) Uani D U P . . .
Cl31 Cl 0.4232(9) 0.3950(7) 0.8485(4) 0.1715 0.411(5) Uani D U P . . .
Cl32 Cl 0.5449(7) 0.5637(8) 0.8193(4) 0.1796 0.411(5) Uani D U P . . .
O1 O 0.5824(3) 0.5228(2) 0.56336(12) 0.0498 1.0000 Uani . . . . . .
O2 O 0.2808(3) 0.65843(18) 0.42291(12) 0.0401 1.0000 Uani . . . . . .
O3 O 0.4471(3) 0.75362(17) 0.43270(12) 0.0384 1.0000 Uani . . . . . .
O4 O 0.4106(3) 0.9503(2) 0.46628(15) 0.0529 1.0000 Uani . . . . . .
O5 O 0.1371(3) 0.4974(2) 0.49689(17) 0.0615 1.0000 Uani . . . . . .
O6 O 0.5410(3) 0.2994(2) 0.46072(12) 0.0401 1.0000 Uani . . . . . .
O7 O 0.3581(3) 0.22133(17) 0.45054(11) 0.0375 1.0000 Uani . . . . . .
O8 O 0.2602(3) 0.0747(2) 0.51187(14) 0.0484 1.0000 Uani . . . . . .
N1 N 0.3399(4) 0.6830(2) 0.53883(14) 0.0416 1.0000 Uani . . . . . .
N2 N 0.5510(3) 0.5465(2) 0.45355(14) 0.0368 1.0000 Uani . . . . . .
N3 N 0.3638(3) 0.3514(3) 0.55118(15) 0.0468 1.0000 Uani . . . . . .
N4 N 0.2887(4) 0.4244(3) 0.41744(17) 0.0493 1.0000 Uani . . . . . .
C1 C 0.3409(5) 0.6785(3) 0.59271(19) 0.0509 1.0000 Uani . . . . . .
C2 C 0.2638(6) 0.7238(4) 0.6269(2) 0.0660 1.0000 Uani . . . . . .
C3 C 0.2831(7) 0.7121(5) 0.6786(3) 0.0888 1.0000 Uani . . . . . .
C4 C 0.3775(8) 0.6534(6) 0.6975(3) 0.1046 1.0000 Uani . . . . . .
C5 C 0.4530(7) 0.6055(5) 0.6634(2) 0.0855 1.0000 Uani . . . . . .
C6 C 0.4339(5) 0.6192(4) 0.6108(2) 0.0548 1.0000 Uani . . . . . .
C7 C 0.4936(4) 0.5782(3) 0.56584(18) 0.0439 1.0000 Uani . . . . . .
C8 C 0.4312(4) 0.6188(3) 0.52165(17) 0.0368 1.0000 Uani . . . . . .
C9 C 0.4650(4) 0.6074(3) 0.47209(17) 0.0367 1.0000 Uani . . . . . .
C10 C 0.4139(4) 0.6614(3) 0.42638(17) 0.0357 1.0000 Uani . . . . . .
C11 C 0.4817(4) 0.6195(3) 0.38221(17) 0.0368 1.0000 Uani . . . . . .
C12 C 0.4790(5) 0.6423(3) 0.33005(19) 0.0503 1.0000 Uani . . . . . .
C13 C 0.5568(6) 0.5933(3) 0.29651(19) 0.0560 1.0000 Uani . . . . . .
C14 C 0.6349(5) 0.5270(4) 0.31550(19) 0.0563 1.0000 Uani . . . . . .
C15 C 0.6389(5) 0.5046(3) 0.36710(18) 0.0457 1.0000 Uani . . . . . .
C16 C 0.5614(4) 0.5522(3) 0.39994(17) 0.0374 1.0000 Uani . . . . . .
C17 C 0.2218(4) 0.7010(3) 0.5116(2) 0.0466 1.0000 Uani . . . . . .
C18 C 0.2361(4) 0.7299(3) 0.45558(19) 0.0426 1.0000 Uani . . . . . .
C19 C 0.3321(4) 0.8034(3) 0.44452(18) 0.0403 1.0000 Uani . . . . . .
C20 C 0.3559(5) 0.8688(3) 0.4862(2) 0.0488 1.0000 Uani . . . . . .
C21 C 0.3031(5) 0.3812(4) 0.5950(2) 0.0567 1.0000 Uani . . . . . .
C22 C 0.3250(6) 0.3588(6) 0.6470(2) 0.0818 1.0000 Uani . . . . . .
C23 C 0.2453(7) 0.3973(7) 0.6835(3) 0.1088 1.0000 Uani . . . . . .
C24 C 0.1467(6) 0.4548(6) 0.6697(3) 0.1032 1.0000 Uani . . . . . .
C25 C 0.1265(6) 0.4777(4) 0.6195(3) 0.0796 1.0000 Uani . . . . . .
C26 C 0.2060(5) 0.4421(4) 0.5811(2) 0.0612 1.0000 Uani . . . . . .
C27 C 0.2087(4) 0.4540(3) 0.5263(2) 0.0502 1.0000 Uani . . . . . .
C28 C 0.3119(4) 0.3963(3) 0.50871(19) 0.0412 1.0000 Uani . . . . . .
C29 C 0.3381(4) 0.3798(3) 0.45900(18) 0.0375 1.0000 Uani . . . . . .
C30 C 0.4210(4) 0.3044(3) 0.43853(17) 0.0382 1.0000 Uani . . . . . .
C31 C 0.4225(5) 0.3215(3) 0.38171(18) 0.0427 1.0000 Uani . . . . . .
C32 C 0.4911(6) 0.2807(3) 0.34368(18) 0.0567 1.0000 Uani . . . . . .
C33 C 0.4760(8) 0.3102(4) 0.2932(2) 0.0752 1.0000 Uani . . . . . .
C34 C 0.3918(8) 0.3778(5) 0.2833(3) 0.0844 1.0000 Uani . . . . . .
C35 C 0.3211(7) 0.4216(4) 0.3213(2) 0.0730 1.0000 Uani . . . . . .
C36 C 0.3395(5) 0.3917(3) 0.3712(2) 0.0491 1.0000 Uani . . . . . .
C37 C 0.4902(4) 0.3113(3) 0.55263(18) 0.0443 1.0000 Uani . . . . . .
C38 C 0.5246(4) 0.2504(3) 0.50754(17) 0.0417 1.0000 Uani . . . . . .
C39 C 0.4282(4) 0.1786(3) 0.49135(17) 0.0355 1.0000 Uani . . . . . .
C40 C 0.3413(4) 0.1420(3) 0.53205(17) 0.0403 1.0000 Uani . . . . . .
C41 C 0.7774(6) 0.4314(4) 0.6399(2) 0.0665 1.0000 Uani . . . . . .
C91 C 0.507(2) 0.3672(8) 0.8425(3) 0.1044 0.439(5) Uani D U P . . .
C92 C 0.5261(18) 0.4099(11) 0.8296(4) 0.0807 0.150(6) Uani D U P . . .
C93 C 0.5630(14) 0.4489(10) 0.8306(14) 0.1720 0.411(5) Uani D U P . . .
H1 H 0.4797 0.9664 0.4775 0.0631 1.0000 Uiso . . . . . .
H2 H 0.5899 0.5061 0.4729 0.0452 1.0000 Uiso . . . . . .
H3 H 0.3053 0.0478 0.4919 0.0718 1.0000 Uiso . . . . . .
H4 H 0.2282 0.4623 0.4205 0.0602 1.0000 Uiso . . . . . .
H21 H 0.2017 0.7625 0.6153 0.0764 1.0000 Uiso R . . . . .
H31 H 0.2323 0.7411 0.7026 0.1048 1.0000 Uiso R . . . . .
H41 H 0.3939 0.6516 0.7337 0.1246 1.0000 Uiso R . . . . .
H51 H 0.5139 0.5660 0.6761 0.1020 1.0000 Uiso R . . . . .
H121 H 0.4258 0.6883 0.3171 0.0609 1.0000 Uiso R . . . . .
H131 H 0.5538 0.6053 0.2614 0.0680 1.0000 Uiso R . . . . .
H141 H 0.6857 0.4958 0.2921 0.0660 1.0000 Uiso R . . . . .
H151 H 0.6931 0.4598 0.3791 0.0559 1.0000 Uiso R . . . . .
H171 H 0.1794 0.7484 0.5299 0.0556 1.0000 Uiso R . . . . .
H172 H 0.1670 0.6470 0.5119 0.0557 1.0000 Uiso R . . . . .
H181 H 0.1516 0.7490 0.4431 0.0493 1.0000 Uiso R . . . . .
H191 H 0.3092 0.8366 0.4145 0.0501 1.0000 Uiso R . . . . .
H201 H 0.4143 0.8408 0.5111 0.0595 1.0000 Uiso R . . . . .
H202 H 0.2771 0.8825 0.5033 0.0597 1.0000 Uiso R . . . . .
H221 H 0.3910 0.3186 0.6564 0.0992 1.0000 Uiso R . . . . .
H231 H 0.2605 0.3833 0.7192 0.1349 1.0000 Uiso R . . . . .
H241 H 0.0947 0.4779 0.6955 0.1192 1.0000 Uiso R . . . . .
H251 H 0.0616 0.5176 0.6109 0.0969 1.0000 Uiso R . . . . .
H321 H 0.5458 0.2357 0.3508 0.0691 1.0000 Uiso R . . . . .
H331 H 0.5228 0.2842 0.2661 0.0904 1.0000 Uiso R . . . . .
H341 H 0.3821 0.3961 0.2492 0.1018 1.0000 Uiso R . . . . .
H351 H 0.2650 0.4669 0.3128 0.0882 1.0000 Uiso R . . . . .
H371 H 0.4944 0.2756 0.5837 0.0550 1.0000 Uiso R . . . . .
H372 H 0.5553 0.3580 0.5539 0.0547 1.0000 Uiso R . . . . .
H381 H 0.6057 0.2225 0.5150 0.0489 1.0000 Uiso R . . . . .
H391 H 0.4753 0.1286 0.4765 0.0439 1.0000 Uiso R . . . . .
H401 H 0.3905 0.1188 0.5597 0.0496 1.0000 Uiso R . . . . .
H402 H 0.2893 0.1909 0.5441 0.0499 1.0000 Uiso R . . . . .
H411 H 0.8575 0.4025 0.6289 0.0819 1.0000 Uiso R . . . . .
H412 H 0.7281 0.4445 0.6084 0.0823 1.0000 Uiso R . . . . .
H911 H 0.5924 0.3477 0.8420 0.1410 0.439 Uiso R . . . . .
H912 H 0.4527 0.3174 0.8482 0.1410 0.439 Uiso R . . . . .
H921 H 0.6067 0.3819 0.8269 0.1065 0.150 Uiso R . . . . .
H931 H 0.6252 0.4399 0.8565 0.1971 0.411 Uiso R . . . . .
H932 H 0.5921 0.4243 0.7990 0.1971 0.411 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.97(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C41 . 1.763(6) yes
Cl2 . C41 . 1.772(6) yes
Cl11 . C91 . 1.765(9) yes
Cl12 . C91 . 1.749(9) yes
Cl21 . C91 . 1.765(9) yes
Cl21 . C92 . 1.753(10) yes
Cl22 . C92 . 1.748(10) yes
Cl23 . C92 . 1.745(10) yes
Cl31 . C93 . 1.745(9) yes
Cl32 . C93 . 1.750(9) yes
O1 . C7 . 1.252(5) yes
O2 . C10 . 1.408(5) yes
O2 . C18 . 1.443(5) yes
O3 . C10 . 1.432(5) yes
O3 . C19 . 1.456(5) yes
O4 . C20 . 1.444(5) yes
O4 . H1 . 0.821 no
O5 . C27 . 1.255(6) yes
O6 . C30 . 1.393(5) yes
O6 . C38 . 1.429(5) yes
O7 . C30 . 1.442(5) yes
O7 . C39 . 1.441(5) yes
O8 . C40 . 1.421(5) yes
O8 . H3 . 0.810 no
N1 . C1 . 1.400(6) yes
N1 . C8 . 1.431(5) yes
N1 . C17 . 1.458(6) yes
N2 . C9 . 1.371(5) yes
N2 . C16 . 1.398(5) yes
N2 . H2 . 0.886 no
N3 . C21 . 1.379(6) yes
N3 . C28 . 1.402(6) yes
N3 . C37 . 1.463(6) yes
N4 . C29 . 1.371(6) yes
N4 . C36 . 1.403(7) yes
N4 . H4 . 0.857 no
C1 . C2 . 1.382(7) yes
C1 . C6 . 1.402(7) yes
C2 . C3 . 1.367(9) yes
C2 . H21 . 0.924 no
C3 . C4 . 1.416(9) yes
C3 . H31 . 0.930 no
C4 . C5 . 1.390(8) yes
C4 . H41 . 0.954 no
C5 . C6 . 1.396(8) yes
C5 . H51 . 0.933 no
C6 . C7 . 1.461(7) yes
C7 . C8 . 1.455(6) yes
C8 . C9 . 1.346(6) yes
C9 . C10 . 1.533(6) yes
C10 . C11 . 1.489(6) yes
C11 . C12 . 1.396(6) yes
C11 . C16 . 1.389(6) yes
C12 . C13 . 1.403(7) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.379(8) yes
C13 . H131 . 0.930 no
C14 . C15 . 1.381(7) yes
C14 . H141 . 0.934 no
C15 . C16 . 1.380(6) yes
C15 . H151 . 0.933 no
C17 . C18 . 1.524(7) yes
C17 . H171 . 0.962 no
C17 . H172 . 0.992 no
C18 . C19 . 1.521(6) yes
C18 . H181 . 0.992 no
C19 . C20 . 1.479(6) yes
C19 . H191 . 0.955 no
C20 . H201 . 0.985 no
C20 . H202 . 0.965 no
C21 . C22 . 1.410(8) yes
C21 . C26 . 1.417(8) yes
C22 . C23 . 1.391(10) yes
C22 . H221 . 0.952 no
C23 . C24 . 1.397(12) yes
C23 . H231 . 0.964 no
C24 . C25 . 1.364(11) yes
C24 . H241 . 0.932 no
C25 . C26 . 1.407(7) yes
C25 . H251 . 0.935 no
C26 . C27 . 1.435(8) yes
C27 . C28 . 1.461(6) yes
C28 . C29 . 1.342(6) yes
C29 . C30 . 1.522(6) yes
C30 . C31 . 1.497(6) yes
C31 . C32 . 1.367(7) yes
C31 . C36 . 1.393(7) yes
C32 . C33 . 1.391(8) yes
C32 . H321 . 0.906 no
C33 . C34 . 1.370(10) yes
C33 . H331 . 0.943 no
C34 . C35 . 1.400(10) yes
C34 . H341 . 0.931 no
C35 . C36 . 1.383(7) yes
C35 . H351 . 0.925 no
C37 . C38 . 1.527(6) yes
C37 . H371 . 0.969 no
C37 . H372 . 0.979 no
C38 . C39 . 1.537(6) yes
C38 . H381 . 0.972 no
C39 . C40 . 1.502(6) yes
C39 . H391 . 0.976 no
C40 . H401 . 0.950 no
C40 . H402 . 0.966 no
C41 . H411 . 0.991 no
C41 . H412 . 0.988 no
C91 . H911 . 0.950 no
C91 . H912 . 0.950 no
C92 . H921 . 0.950 no
C93 . H931 . 0.950 no
C93 . H932 . 0.950 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
C10 . O2 . C18 . 105.4(3) yes
C10 . O3 . C19 . 108.1(3) yes
C20 . O4 . H1 . 118.4 no
C30 . O6 . C38 . 105.6(3) yes
C30 . O7 . C39 . 107.7(3) yes
C40 . O8 . H3 . 103.5 no
C1 . N1 . C8 . 105.9(4) yes
C1 . N1 . C17 . 120.0(4) yes
C8 . N1 . C17 . 123.2(4) yes
C9 . N2 . C16 . 111.2(3) yes
C9 . N2 . H2 . 124.0 no
C16 . N2 . H2 . 124.7 no
C21 . N3 . C28 . 108.2(4) yes
C21 . N3 . C37 . 122.3(4) yes
C28 . N3 . C37 . 124.9(4) yes
C29 . N4 . C36 . 111.0(4) yes
C29 . N4 . H4 . 122.1 no
C36 . N4 . H4 . 126.5 no
N1 . C1 . C2 . 127.8(5) yes
N1 . C1 . C6 . 111.7(4) yes
C2 . C1 . C6 . 120.4(5) yes
C1 . C2 . C3 . 118.7(5) yes
C1 . C2 . H21 . 121.0 no
C3 . C2 . H21 . 120.3 no
C2 . C3 . C4 . 121.7(6) yes
C2 . C3 . H31 . 120.9 no
C4 . C3 . H31 . 117.4 no
C3 . C4 . C5 . 120.0(6) yes
C3 . C4 . H41 . 119.1 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 117.7(6) yes
C4 . C5 . H51 . 119.6 no
C6 . C5 . H51 . 122.7 no
C1 . C6 . C5 . 121.4(5) yes
C1 . C6 . C7 . 107.4(4) yes
C5 . C6 . C7 . 131.1(5) yes
C6 . C7 . O1 . 129.9(4) yes
C6 . C7 . C8 . 105.0(4) yes
O1 . C7 . C8 . 125.0(4) yes
C7 . C8 . N1 . 109.8(4) yes
C7 . C8 . C9 . 125.5(4) yes
N1 . C8 . C9 . 124.2(4) yes
N2 . C9 . C8 . 126.5(4) yes
N2 . C9 . C10 . 108.1(4) yes
C8 . C9 . C10 . 125.4(4) yes
C9 . C10 . O3 . 109.4(3) yes
C9 . C10 . O2 . 112.6(3) yes
O3 . C10 . O2 . 106.4(3) yes
C9 . C10 . C11 . 101.8(3) yes
O3 . C10 . C11 . 112.0(3) yes
O2 . C10 . C11 . 114.6(4) yes
C10 . C11 . C12 . 129.4(4) yes
C10 . C11 . C16 . 109.9(4) yes
C12 . C11 . C16 . 120.6(4) yes
C11 . C12 . C13 . 117.6(4) yes
C11 . C12 . H121 . 122.1 no
C13 . C12 . H121 . 120.3 no
C12 . C13 . C14 . 120.2(5) yes
C12 . C13 . H131 . 119.2 no
C14 . C13 . H131 . 120.6 no
C13 . C14 . C15 . 122.6(5) yes
C13 . C14 . H141 . 118.0 no
C15 . C14 . H141 . 119.4 no
C14 . C15 . C16 . 117.1(5) yes
C14 . C15 . H151 . 121.1 no
C16 . C15 . H151 . 121.8 no
N2 . C16 . C11 . 109.0(4) yes
N2 . C16 . C15 . 129.1(4) yes
C11 . C16 . C15 . 121.9(4) yes
N1 . C17 . C18 . 115.4(4) yes
N1 . C17 . H171 . 107.1 no
C18 . C17 . H171 . 108.0 no
N1 . C17 . H172 . 110.1 no
C18 . C17 . H172 . 107.2 no
H171 . C17 . H172 . 108.8 no
C17 . C18 . O2 . 112.6(3) yes
C17 . C18 . C19 . 116.8(4) yes
O2 . C18 . C19 . 101.8(3) yes
C17 . C18 . H181 . 107.8 no
O2 . C18 . H181 . 108.3 no
C19 . C18 . H181 . 109.2 no
C18 . C19 . O3 . 103.1(3) yes
C18 . C19 . C20 . 116.9(4) yes
O3 . C19 . C20 . 110.5(4) yes
C18 . C19 . H191 . 111.1 no
O3 . C19 . H191 . 107.7 no
C20 . C19 . H191 . 107.2 no
C19 . C20 . O4 . 111.3(4) yes
C19 . C20 . H201 . 107.8 no
O4 . C20 . H201 . 110.0 no
C19 . C20 . H202 . 109.3 no
O4 . C20 . H202 . 109.3 no
H201 . C20 . H202 . 109.1 no
N3 . C21 . C22 . 129.6(5) yes
N3 . C21 . C26 . 109.5(5) yes
C22 . C21 . C26 . 121.0(5) yes
C21 . C22 . C23 . 117.0(7) yes
C21 . C22 . H221 . 121.1 no
C23 . C22 . H221 . 121.9 no
C22 . C23 . C24 . 122.1(7) yes
C22 . C23 . H231 . 117.7 no
C24 . C23 . H231 . 120.2 no
C23 . C24 . C25 . 121.0(6) yes
C23 . C24 . H241 . 118.8 no
C25 . C24 . H241 . 120.2 no
C24 . C25 . C26 . 119.3(7) yes
C24 . C25 . H251 . 120.1 no
C26 . C25 . H251 . 120.6 no
C21 . C26 . C25 . 119.6(6) yes
C21 . C26 . C27 . 108.5(4) yes
C25 . C26 . C27 . 131.9(6) yes
C26 . C27 . O5 . 130.9(5) yes
C26 . C27 . C28 . 104.5(5) yes
O5 . C27 . C28 . 124.3(5) yes
C27 . C28 . N3 . 109.2(4) yes
C27 . C28 . C29 . 124.2(4) yes
N3 . C28 . C29 . 125.9(4) yes
N4 . C29 . C28 . 126.1(4) yes
N4 . C29 . C30 . 107.7(4) yes
C28 . C29 . C30 . 126.2(4) yes
C29 . C30 . O7 . 107.3(3) yes
C29 . C30 . O6 . 114.8(3) yes
O7 . C30 . O6 . 106.4(3) yes
C29 . C30 . C31 . 103.0(4) yes
O7 . C30 . C31 . 111.4(3) yes
O6 . C30 . C31 . 114.0(4) yes
C30 . C31 . C32 . 129.9(5) yes
C30 . C31 . C36 . 108.3(4) yes
C32 . C31 . C36 . 121.8(5) yes
C31 . C32 . C33 . 118.5(6) yes
C31 . C32 . H321 . 121.4 no
C33 . C32 . H321 . 120.0 no
C32 . C33 . C34 . 119.0(6) yes
C32 . C33 . H331 . 120.8 no
C34 . C33 . H331 . 120.2 no
C33 . C34 . C35 . 123.9(6) yes
C33 . C34 . H341 . 117.8 no
C35 . C34 . H341 . 118.2 no
C34 . C35 . C36 . 115.7(6) yes
C34 . C35 . H351 . 121.0 no
C36 . C35 . H351 . 123.3 no
N4 . C36 . C31 . 109.5(4) yes
N4 . C36 . C35 . 129.4(5) yes
C31 . C36 . C35 . 121.0(5) yes
N3 . C37 . C38 . 116.2(4) yes
N3 . C37 . H371 . 106.8 no
C38 . C37 . H371 . 107.4 no
N3 . C37 . H372 . 110.5 no
C38 . C37 . H372 . 106.5 no
H371 . C37 . H372 . 109.3 no
C37 . C38 . O6 . 112.0(4) yes
C37 . C38 . C39 . 117.9(4) yes
O6 . C38 . C39 . 101.8(3) yes
C37 . C38 . H381 . 108.2 no
O6 . C38 . H381 . 106.4 no
C39 . C38 . H381 . 109.8 no
C38 . C39 . O7 . 103.4(3) yes
C38 . C39 . C40 . 117.8(4) yes
O7 . C39 . C40 . 111.4(3) yes
C38 . C39 . H391 . 107.7 no
O7 . C39 . H391 . 108.1 no
C40 . C39 . H391 . 108.0 no
C39 . C40 . O8 . 111.5(4) yes
C39 . C40 . H401 . 109.2 no
O8 . C40 . H401 . 110.4 no
C39 . C40 . H402 . 107.4 no
O8 . C40 . H402 . 108.2 no
H401 . C40 . H402 . 110.0 no
Cl2 . C41 . Cl1 . 111.0(3) yes
Cl2 . C41 . H411 . 109.5 no
Cl1 . C41 . H411 . 107.7 no
Cl2 . C41 . H412 . 112.6 no
Cl1 . C41 . H412 . 108.5 no
H411 . C41 . H412 . 107.5 no
Cl11 . C91 . Cl12 . 111.0(6) yes
Cl11 . C91 . H911 . 104.7 no
Cl12 . C91 . H911 . 104.5 no
Cl11 . C91 . H912 . 112.7 no
Cl12 . C91 . H912 . 113.7 no
H911 . C91 . H912 . 109.5 no
Cl21 . C92 . Cl22 . 108.6(8) yes
Cl21 . C92 . Cl23 . 108.6(9) yes
Cl22 . C92 . Cl23 . 106.4(10) yes
Cl21 . C92 . H921 . 110.2 no
Cl22 . C92 . H921 . 111.7 no
Cl23 . C92 . H921 . 111.2 no
Cl32 . C93 . Cl31 . 113.9(9) yes
Cl32 . C93 . H931 . 109.4 no
Cl31 . C93 . H931 . 109.2 no
Cl32 . C93 . H932 . 105.7 no
Cl31 . C93 . H932 . 109.0 no
H931 . C93 . H932 . 109.5 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
O4 . H1 . O5 2_566 180 0.82 1.87 2.691(5) yes
N2 . H2 . O8 2_556 149 0.89 2.20 2.994(4) yes
O8 . H3 . O4 1_545 157 0.81 1.95 2.715(5) yes
N4 . H4 . O5 . 123 0.86 2.27 2.829(6) yes


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O2 C10 O3 -33.1(4) . . . . no
C18 O2 C10 C9 86.6(4) . . . . no
C18 O2 C10 C11 -157.5(4) . . . . no
C10 O2 C18 C17 -86.5(4) . . . . no
C10 O2 C18 C19 39.4(4) . . . . no
C19 O3 C10 O2 12.6(4) . . . . no
C19 O3 C10 C9 -109.3(4) . . . . no
C19 O3 C10 C11 138.6(4) . . . . no
C10 O3 C19 C18 11.5(4) . . . . no
C10 O3 C19 C20 137.1(4) . . . . no
C38 O6 C30 C31 -158.2(4) . . . . no
C30 O6 C38 C37 -87.9(4) . . . . no
C30 O6 C38 C39 39.0(4) . . . . no
C38 O6 C30 C29 83.5(4) . . . . no
C38 O6 C30 O7 -35.0(4) . . . . no
C39 O7 C30 C29 -107.7(4) . . . . no
C39 O7 C30 O6 15.6(4) . . . . no
C30 O7 C39 C40 135.8(4) . . . . no
C39 O7 C30 C31 140.4(4) . . . . no
C30 O7 C39 C38 8.4(4) . . . . no
C8 N1 C1 C6 4.0(5) . . . . no
C1 N1 C8 C7 -3.2(5) . . . . no
C17 N1 C1 C2 -30.5(7) . . . . no
C17 N1 C1 C6 149.3(4) . . . . no
C8 N1 C1 C2 -175.9(5) . . . . no
C1 N1 C8 C9 -175.0(4) . . . . no
C17 N1 C8 C7 -147.1(4) . . . . no
C17 N1 C8 C9 41.2(6) . . . . no
C1 N1 C17 C18 163.7(4) . . . . no
C8 N1 C17 C18 -57.1(5) . . . . no
C16 N2 C9 C8 179.1(4) . . . . no
C16 N2 C9 C10 -1.4(5) . . . . no
C9 N2 C16 C15 178.3(5) . . . . no
C9 N2 C16 C11 0.9(5) . . . . no
C37 N3 C21 C22 -20.1(9) . . . . no
C37 N3 C21 C26 160.4(4) . . . . no
C28 N3 C21 C26 3.3(6) . . . . no
C21 N3 C28 C29 -173.7(5) . . . . no
C37 N3 C28 C27 -159.4(4) . . . . no
C21 N3 C28 C27 -3.1(5) . . . . no
C28 N3 C21 C22 -177.3(6) . . . . no
C21 N3 C37 C38 157.3(5) . . . . no
C28 N3 C37 C38 -49.5(6) . . . . no
C37 N3 C28 C29 30.0(7) . . . . no
C36 N4 C29 C28 178.2(4) . . . . no
C29 N4 C36 C31 1.8(6) . . . . no
C29 N4 C36 C35 -175.6(6) . . . . no
C36 N4 C29 C30 -5.5(5) . . . . no
N1 C1 C2 C3 -177.9(6) . . . . no
C6 C1 C2 C3 2.3(9) . . . . no
N1 C1 C6 C5 178.9(5) . . . . no
N1 C1 C6 C7 -3.2(6) . . . . no
C2 C1 C6 C5 -1.3(9) . . . . no
C2 C1 C6 C7 176.6(5) . . . . no
C1 C2 C3 C4 -1.6(10) . . . . no
C2 C3 C4 C5 -0.3(12) . . . . no
C3 C4 C5 C6 1.4(11) . . . . no
C4 C5 C6 C1 -0.7(10) . . . . no
C4 C5 C6 C7 -177.9(6) . . . . no
C5 C6 C7 C8 178.7(6) . . . . no
C1 C6 C7 O1 178.5(5) . . . . no
C1 C6 C7 C8 1.1(5) . . . . no
C5 C6 C7 O1 -3.9(10) . . . . no
C6 C7 C8 N1 1.3(5) . . . . no
C6 C7 C8 C9 172.9(5) . . . . no
O1 C7 C8 C9 -4.6(7) . . . . no
O1 C7 C8 N1 -176.3(4) . . . . no
N1 C8 C9 N2 -179.4(4) . . . . no
C7 C8 C9 C10 -169.5(4) . . . . no
N1 C8 C9 C10 1.0(7) . . . . no
C7 C8 C9 N2 10.1(7) . . . . no
N2 C9 C10 O2 124.5(4) . . . . no
N2 C9 C10 O3 -117.5(4) . . . . no
N2 C9 C10 C11 1.2(4) . . . . no
C8 C9 C10 O2 -55.9(6) . . . . no
C8 C9 C10 O3 62.2(5) . . . . no
C8 C9 C10 C11 -179.1(4) . . . . no
O2 C10 C11 C12 61.2(6) . . . . no
O3 C10 C11 C12 -60.2(6) . . . . no
O3 C10 C11 C16 116.1(4) . . . . no
C9 C10 C11 C12 -177.0(5) . . . . no
C9 C10 C11 C16 -0.7(5) . . . . no
O2 C10 C11 C16 -122.6(4) . . . . no
C16 C11 C12 C13 1.6(7) . . . . no
C10 C11 C16 N2 0.0(5) . . . . no
C10 C11 C12 C13 177.5(5) . . . . no
C10 C11 C16 C15 -177.6(4) . . . . no
C12 C11 C16 N2 176.6(4) . . . . no
C12 C11 C16 C15 -1.0(7) . . . . no
C11 C12 C13 C14 -1.8(8) . . . . no
C12 C13 C14 C15 1.3(8) . . . . no
C13 C14 C15 C16 -0.6(8) . . . . no
C14 C15 C16 N2 -176.7(5) . . . . no
C14 C15 C16 C11 0.5(7) . . . . no
N1 C17 C18 O2 69.2(5) . . . . no
N1 C17 C18 C19 -48.1(5) . . . . no
O2 C18 C19 C20 -151.9(4) . . . . no
C17 C18 C19 O3 92.4(4) . . . . no
O2 C18 C19 O3 -30.6(4) . . . . no
C17 C18 C19 C20 -28.9(6) . . . . no
C18 C19 C20 O4 -159.5(4) . . . . no
O3 C19 C20 O4 83.1(5) . . . . no
N3 C21 C22 C23 -177.8(7) . . . . no
C26 C21 C22 C23 1.6(10) . . . . no
N3 C21 C26 C25 176.6(5) . . . . no
N3 C21 C26 C27 -2.3(6) . . . . no
C22 C21 C26 C25 -2.9(9) . . . . no
C22 C21 C26 C27 178.2(6) . . . . no
C21 C22 C23 C24 0.8(13) . . . . no
C22 C23 C24 C25 -1.8(13) . . . . no
C23 C24 C25 C26 0.5(11) . . . . no
C24 C25 C26 C21 1.8(9) . . . . no
C24 C25 C26 C27 -179.5(6) . . . . no
C21 C26 C27 O5 175.7(5) . . . . no
C21 C26 C27 C28 0.4(6) . . . . no
C25 C26 C27 O5 -3.1(10) . . . . no
C25 C26 C27 C28 -178.3(6) . . . . no
O5 C27 C28 N3 -174.1(4) . . . . no
O5 C27 C28 C29 -3.3(7) . . . . no
C26 C27 C28 N3 1.6(5) . . . . no
C26 C27 C28 C29 172.4(5) . . . . no
N3 C28 C29 N4 -179.1(4) . . . . no
N3 C28 C29 C30 5.3(7) . . . . no
C27 C28 C29 N4 11.7(7) . . . . no
C27 C28 C29 C30 -164.0(4) . . . . no
N4 C29 C30 O6 131.2(4) . . . . no
N4 C29 C30 O7 -110.8(4) . . . . no
N4 C29 C30 C31 6.8(5) . . . . no
C28 C29 C30 O6 -52.5(6) . . . . no
C28 C29 C30 O7 65.5(5) . . . . no
C28 C29 C30 C31 -176.9(4) . . . . no
O6 C30 C31 C32 48.2(7) . . . . no
O6 C30 C31 C36 -130.6(4) . . . . no
O7 C30 C31 C32 -72.3(7) . . . . no
O7 C30 C31 C36 108.9(4) . . . . no
C29 C30 C31 C32 173.1(5) . . . . no
C29 C30 C31 C36 -5.8(5) . . . . no
C30 C31 C32 C33 -179.3(5) . . . . no
C36 C31 C32 C33 -0.5(8) . . . . no
C30 C31 C36 N4 2.9(6) . . . . no
C30 C31 C36 C35 -179.5(5) . . . . no
C32 C31 C36 N4 -176.1(5) . . . . no
C32 C31 C36 C35 1.5(8) . . . . no
C31 C32 C33 C34 -1.0(10) . . . . no
C32 C33 C34 C35 1.8(12) . . . . no
C33 C34 C35 C36 -0.8(11) . . . . no
C34 C35 C36 N4 176.3(6) . . . . no
C34 C35 C36 C31 -0.8(9) . . . . no
N3 C37 C38 O6 69.8(5) . . . . no
N3 C37 C38 C39 -47.9(5) . . . . no
O6 C38 C39 O7 -28.4(4) . . . . no
O6 C38 C39 C40 -151.7(4) . . . . no
C37 C38 C39 O7 94.6(4) . . . . no
C37 C38 C39 C40 -28.7(6) . . . . no
O7 C39 C40 O8 62.5(5) . . . . no
C38 C39 C40 O8 -178.4(3) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
Cl1 Cl12 3.639(5) . . no
Cl11 O2 3.443(4) . 4_565 no
Cl11 O5 3.178(5) . 4_565 no
Cl12 C23 3.620(9) . . no
Cl12 Cl1 3.639(5) . . no
Cl21 O5 3.178(5) . 4_565 no
Cl21 O2 3.443(4) . 4_565 no
Cl22 C4 3.60(2) . 3_646 no
Cl23 C4 3.58(2) . . no
Cl31 O2 3.001(10) . 4_565 no
Cl32 C14 3.643(10) . 4_665 no
O1 N2 2.891(5) . . no
O1 C37 3.318(5) . . no
O1 C41 3.170(7) . . no
O1 O8 3.075(5) . 2_556 no
O2 N1 3.095(5) . . no
O3 C17 3.311(5) . 2_566 no
O3 N1 3.160(5) . . no
O3 O4 3.089(4) . . no
O4 O8 2.716(5) . 1_565 no
O4 C40 3.414(6) . 1_565 no
O4 O5 2.691(5) . 2_566 no
O4 C25 3.363(8) . 2_566 no
O5 N4 2.829(6) . . no
O5 C17 3.194(5) . . no
O6 N3 3.101(5) . . no
O6 O8 3.066(4) . 2_556 no
O6 C40 3.294(5) . 2_556 no
O7 O8 2.899(4) . . no
O7 C41 3.383(6) . 2_456 no
O7 N3 3.256(5) . . no
O7 N4 3.237(5) . . no
O8 C20 3.306(6) . 1_545 no
O8 N2 2.994(4) . 2_456 no
N1 C20 3.099(6) . . no
N2 C29 3.358(5) . . no
N3 C40 3.177(6) . . no
C2 C91 3.328(18) . 3_656 no
C3 C92 3.583(19) . 3_656 no
C3 C91 3.253(18) . 3_656 no
C3 C34 3.549(11) . 4_565 no
C4 C91 3.573(16) . 3_656 no
C8 C19 3.565(6) . . no
C8 C27 3.405(6) . . no
C8 C28 3.571(6) . . no
C14 C93 3.233(16) . 4_664 no
C14 C34 3.501(10) . . no
C14 Cl32 3.643(10) . 4_664 no
C15 C36 3.584(7) . . no
C15 C93 3.359(18) . 4_664 no
C15 C31 3.584(7) . . no
C16 C36 3.434(7) . . no
C27 C39 3.592(6) . 2_456 no
C28 C39 3.506(6) . . no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/10/16 at 14:54:26
#
#LIST     12                                                                    
BLOCK SCALE X'S, CL(1,U'S) UNTIL CL(2) 
CONT CL(11,U'S,OCC) UNTIL CL(32) 
CONT O(1,U'S) UNTIL O(8) 
CONT N(1,U'S) UNTIL C(41) C(91,U'S,OCC) UNTIL C(93) 
CONT ENANTIO 
EQUIV CL(11,OCC) CL(12,OCC) C(91,OCC) 
EQUIV CL(21,OCC) CL(22,OCC) CL(23,OCC) C(92,OCC) 
EQUIV CL(31,OCC) CL(32,OCC) C(93,OCC) 
RIDE CL(11,X'S) CL(21,X'S) 
EQUIV CL(11,U[11]) CL(21,U[11]) 
EQUIV CL(11,U[22]) CL(21,U[22]) 
EQUIV CL(11,U[33]) CL(21,U[33]) 
EQUIV CL(11,U[12]) CL(21,U[12]) 
EQUIV CL(11,U[13]) CL(21,U[13]) 
EQUIV CL(11,U[23]) CL(21,U[23]) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  32,X'S) H   ( 321,X'S) 
RIDE C   (  33,X'S) H   ( 331,X'S) 
RIDE C   (  34,X'S) H   ( 341,X'S) 
RIDE C   (  35,X'S) H   ( 351,X'S) 
RIDE C   (  37,X'S) H   ( 371,X'S) H   ( 372,X'S) 
RIDE C   (  38,X'S) H   ( 381,X'S) 
RIDE C   (  39,X'S) H   ( 391,X'S) 
RIDE C   (  40,X'S) H   ( 401,X'S) H   ( 402,X'S) 
RIDE C   (  41,X'S) H   ( 411,X'S) H   ( 412,X'S) 
RIDE C(91,X'S) H(911,X'S) H(912,X'S) 
RIDE C(92,X'S) H(921,X'S) 
RIDE C(93,X'S) H(931,X'S) H(932,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/10/16 at 14:54:26
#
#LIST     16                                                                    
REM U(IJ) 0.0, .01 = CL(3) TO CL(4) 
U(IJ) 0.0, .02 = CL(12) TO CL(11) 
U(IJ) 0.0, .02 = CL(12) TO CL(22) 
U(IJ) 0.0, .02 = CL(12) TO CL(23) 
U(IJ) 0.0, .02 = CL(12) TO CL(31) 
U(IJ) 0.0, .02 = CL(12) TO CL(32) 
REM 
U(IJ) 0.0, .01 = CL(11) TO C(91) 
DIST 1.75, .01 = C(91) TO CL(11) 
DIST 1.75, .01 = C(91) TO CL(12) 
ANGLE 109 2 = CL(11) TO C(91) TO CL(12) 
DIST 2.8, .02 = CL(11) TO CL(12) 
REM 
U(IJ) 0.0, .01 = CL(21) TO C(92) 
DIST 1.75, .01 = C(92) TO CL(21) 
DIST 1.75, .01 = C(92) TO CL(22) 
DIST 1.75, .01 = C(92) TO CL(23) 
ANGLE 109 2 = CL(21) TO C(92) TO CL(22) 
ANGLE 109 2 = CL(21) TO C(92) TO CL(23) 
ANGLE 109 2 = CL(22) TO C(92) TO CL(23) 
DIST 2.8, .02 = CL(21) TO CL(22) 
DIST 2.8, .02 = CL(21) TO CL(23) 
DIST 2.8, .02 = CL(22) TO CL(23) 
REM 
U(IJ) 0.0, .01 = CL(31) TO C(93) 
DIST 1.75, .01 = C(93) TO CL(31) 
DIST 1.75, .01 = C(93) TO CL(32) 
ANGLE 109 2 = CL(31) TO C(93) TO CL(32) 
DIST 2.8, .02 = CL(31) TO CL(32) 
REM 
REM 
SUM  .0001 FOR CL(12,OCC) CL(22,OCC) CL(32,OCC) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 0 x .
0 2 1 x .
0 2 2 x .
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kel1612SNQ
_database_code_depnum_ccdc_archive 'CCDC 1590268'
_audit_update_record             
;
2017-12-10 deposited with the CCDC.
2018-07-16 downloaded from the CCDC.
;
_audit_creation_date             16-12-06
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Z:\kel1612SNQ\Tony_kel1612SNQ_da At 11:52 on'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   8.64640(7)
_cell_length_b                   11.41283(8)
_cell_length_c                   17.69376(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1746.02(2)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_space_group_name_Hall  'P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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 = C22 H18 N2 O4 
# Dc =      1.42 Fooo =    784.00 Mu =      8.14 M =    374.40
# Found Formula = C22 H18 N2 O4 
# Dc =      1.42 FOOO =    784.00 Mu =      8.14 M =    374.40

_chemical_formula_sum            'C22 H18 N2 O4'
_chemical_formula_moiety         'C22 H18 N2 O4'
_chemical_compound_source        ' from U of Wollongong'
_chemical_formula_weight         374.40


_cell_measurement_reflns_used    20161
_cell_measurement_theta_min      5
_cell_measurement_theta_max      74
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_min          0.044
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_max          0.201

_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.814

# Sheldrick geometric approximatio 0.86 0.96 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro version 1.171.38.43 (Rigaku Oxford Diffraction, 2016)
(Release 29 April 2016; compiled 27 May 2016,16:53)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.96
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_measurement_method       'ω scans'


# If a reference occurs more than once, delete the author 
# and date from subsequent references. 

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2016)'

_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    'PLATON (Spek, 2008)'
_diffrn_reflns_av_sigmaI/netI    0.0232

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      150
_diffrn_reflns_number            28445
_reflns_number_total             3528
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections without Friedels Law is 3528 
# Number of reflections with Friedels Law is 2028 
# Theoretical number of reflections is about 1766 


_diffrn_reflns_theta_min         4.610
_diffrn_reflns_theta_max         73.766
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        73.766
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              14
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.72
_oxford_diffrn_Wilson_scale      0.01

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

_refine_diff_density_min         -0.12
_refine_diff_density_max         0.24


# 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>-10.0\s(I)
_refine_ls_number_reflns         3528
_refine_ls_number_restraints     0
_refine_ls_number_parameters     257
_oxford_refine_ls_R_factor_ref   0.0306
_refine_ls_wR_factor_ref         0.0812
_refine_ls_goodness_of_fit_ref   1.0034
_refine_ls_shift/su_max          0.0004552
_refine_ls_shift/su_mean         0.0000611


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3528
_refine_ls_R_factor_all          0.0306
_refine_ls_wR_factor_all         0.0812

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3486
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_gt          0.0807

_refine_ls_abs_structure_Flack   0.11(16)
_refine_ls_abs_structure_details 'Flack (1983), 1500 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.52P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_special_details          
# see also _refine_ls_hydrogen for refinement keywords.                         
;                                                                               


All hydrogen atoms 
 were observed in a difference electron density map
prior to their inclusion.
Those bonded to C were included at calculated positions
and that bonded to O where indicted in the difference map.
They were initially refined with soft restraints on the 
bond lengths and angles to regularise their geometry 
(C---H in the range 0.93--0.98Å, 
O---H = 0.83Å) and with
Uiso(H) in the range 1.2-1.5 times Ueq of the parent atom, 
after which the positions were refined with riding constraints
and the displacement parameters were held fixed. 
The H attached to O4 was allowed to refine freely.


The largest peaks in the final difference electron density map
are located between existing atoms.



;

# 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 0.46662(12) 0.44614(9) 0.56364(6) 0.0322 1.0000 Uani . . . . . .
O2 O 0.67488(12) 0.77342(9) 0.76448(6) 0.0310 1.0000 Uani . . . . . .
O3 O 0.54382(12) 0.61962(9) 0.81304(6) 0.0304 1.0000 Uani . . . . . .
O4 O 0.77591(13) 0.22580(10) 0.49217(7) 0.0365 1.0000 Uani . . . . . .
N1 N 0.39671(15) 0.71052(10) 0.66182(7) 0.0296 1.0000 Uani . . . . . .
N2 N 0.75322(14) 0.52421(10) 0.66645(7) 0.0263 1.0000 Uani . . . . . .
C1 C 0.26886(19) 0.70224(13) 0.61521(9) 0.0304 1.0000 Uani . . . . . .
C2 C 0.1423(2) 0.77752(16) 0.60986(10) 0.0419 1.0000 Uani . . . . . .
C3 C 0.0273(2) 0.74887(17) 0.55873(11) 0.0450 1.0000 Uani . . . . . .
C4 C 0.0360(2) 0.64928(17) 0.51299(10) 0.0411 1.0000 Uani . . . . . .
C5 C 0.16081(19) 0.57488(15) 0.51818(9) 0.0342 1.0000 Uani . . . . . .
C6 C 0.27794(17) 0.60225(12) 0.56968(8) 0.0274 1.0000 Uani . . . . . .
C7 C 0.42328(16) 0.54368(12) 0.58634(8) 0.0255 1.0000 Uani . . . . . .
C8 C 0.50064(16) 0.61803(12) 0.64332(8) 0.0256 1.0000 Uani . . . . . .
C9 C 0.63302(16) 0.59885(11) 0.68406(8) 0.0235 1.0000 Uani . . . . . .
C10 C 0.66528(16) 0.65067(12) 0.76310(8) 0.0240 1.0000 Uani . . . . . .
C11 C 0.81755(16) 0.59687(12) 0.78342(8) 0.0267 1.0000 Uani . . . . . .
C12 C 0.90738(18) 0.61696(13) 0.84703(9) 0.0314 1.0000 Uani . . . . . .
C13 C 1.05143(19) 0.56278(14) 0.85094(10) 0.0375 1.0000 Uani . . . . . .
C14 C 1.10153(19) 0.49281(15) 0.79197(11) 0.0408 1.0000 Uani . . . . . .
C15 C 1.01151(18) 0.47260(15) 0.72788(10) 0.0358 1.0000 Uani . . . . . .
C16 C 0.86702(16) 0.52568(12) 0.72514(9) 0.0282 1.0000 Uani . . . . . .
C17 C 0.4437(2) 0.82268(13) 0.69363(9) 0.0369 1.0000 Uani . . . . . .
C18 C 0.51753(19) 0.81282(14) 0.77128(9) 0.0342 1.0000 Uani . . . . . .
C19 C 0.44497(18) 0.72079(15) 0.82166(9) 0.0351 1.0000 Uani . . . . . .
C20 C 0.77723(17) 0.47443(13) 0.59456(8) 0.0287 1.0000 Uani . . . . . .
C21 C 0.84274(17) 0.37164(13) 0.58287(9) 0.0305 1.0000 Uani . . . . . .
C22 C 0.87158(18) 0.32531(14) 0.50527(9) 0.0344 1.0000 Uani . . . . . .
H1 H 0.839(3) 0.165(2) 0.4729(13) 0.0574 1.0000 Uiso . . . . . .
H21 H 0.1332 0.8460 0.6411 0.0508 1.0000 Uiso R . . . . .
H31 H -0.0619 0.7997 0.5555 0.0535 1.0000 Uiso R . . . . .
H41 H -0.0439 0.6309 0.4769 0.0488 1.0000 Uiso R . . . . .
H51 H 0.1687 0.5051 0.4873 0.0405 1.0000 Uiso R . . . . .
H121 H 0.8688 0.6661 0.8873 0.0384 1.0000 Uiso R . . . . .
H131 H 1.1128 0.5751 0.8964 0.0449 1.0000 Uiso R . . . . .
H141 H 1.1997 0.4547 0.7947 0.0490 1.0000 Uiso R . . . . .
H151 H 1.0440 0.4277 0.6860 0.0429 1.0000 Uiso R . . . . .
H171 H 0.3520 0.8720 0.6970 0.0446 1.0000 Uiso R . . . . .
H172 H 0.5166 0.8641 0.6585 0.0433 1.0000 Uiso R . . . . .
H181 H 0.5189 0.8898 0.7944 0.0422 1.0000 Uiso R . . . . .
H191 H 0.4455 0.7451 0.8744 0.0417 1.0000 Uiso R . . . . .
H192 H 0.3361 0.7002 0.8043 0.0413 1.0000 Uiso R . . . . .
H201 H 0.7445 0.5229 0.5546 0.0270 1.0000 Uiso R . . . . .
H211 H 0.8750 0.3237 0.6255 0.0366 1.0000 Uiso R . . . . .
H221 H 0.9840 0.3022 0.5019 0.0402 1.0000 Uiso R . . . . .
H222 H 0.8481 0.3914 0.4673 0.0407 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          8.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C7 . 1.2414(18) yes
O2 . C10 . 1.4036(16) yes
O2 . C18 . 1.4379(19) yes
O3 . C10 . 1.4175(17) yes
O3 . C19 . 1.4447(18) yes
O4 . C22 . 1.4240(19) yes
O4 . H1 . 0.94(2) no
N1 . C1 . 1.382(2) yes
N1 . C8 . 1.4243(18) yes
N1 . C17 . 1.4562(19) yes
N2 . C9 . 1.3795(18) yes
N2 . C16 . 1.4306(19) yes
N2 . C20 . 1.4085(17) yes
C1 . C2 . 1.395(2) yes
C1 . C6 . 1.399(2) yes
C2 . C3 . 1.383(3) yes
C2 . H21 . 0.960 no
C3 . C4 . 1.397(3) yes
C3 . H31 . 0.967 no
C4 . C5 . 1.376(2) yes
C4 . H41 . 0.964 no
C5 . C6 . 1.398(2) yes
C5 . H51 . 0.968 no
C6 . C7 . 1.454(2) yes
C7 . C8 . 1.4779(19) yes
C8 . C9 . 1.370(2) yes
C9 . C10 . 1.5437(19) yes
C10 . C11 . 1.497(2) yes
C11 . C12 . 1.387(2) yes
C11 . C16 . 1.381(2) yes
C12 . C13 . 1.392(2) yes
C12 . H121 . 0.966 no
C13 . C14 . 1.383(2) yes
C13 . H131 . 0.974 no
C14 . C15 . 1.395(2) yes
C14 . H141 . 0.955 no
C15 . C16 . 1.389(2) yes
C15 . H151 . 0.944 no
C17 . C18 . 1.519(2) yes
C17 . H171 . 0.974 no
C17 . H172 . 1.004 no
C18 . C19 . 1.514(2) yes
C18 . H181 . 0.969 no
C19 . H191 . 0.974 no
C19 . H192 . 1.018 no
C20 . C21 . 1.319(2) yes
C20 . H201 . 0.942 no
C21 . C22 . 1.492(2) yes
C21 . H211 . 0.973 no
C22 . H221 . 1.009 no
C22 . H222 . 1.030 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
C10 . O2 . C18 . 104.93(11) yes
C10 . O3 . C19 . 107.72(11) yes
C22 . O4 . H1 . 107.8(14) no
C1 . N1 . C8 . 108.47(12) yes
C1 . N1 . C17 . 120.91(12) yes
C8 . N1 . C17 . 124.36(13) yes
C9 . N2 . C16 . 110.30(11) yes
C9 . N2 . C20 . 124.35(12) yes
C16 . N2 . C20 . 123.98(12) yes
N1 . C1 . C2 . 128.75(14) yes
N1 . C1 . C6 . 110.76(13) yes
C2 . C1 . C6 . 120.49(15) yes
C1 . C2 . C3 . 117.56(16) yes
C1 . C2 . H21 . 121.7 no
C3 . C2 . H21 . 120.7 no
C2 . C3 . C4 . 122.17(16) yes
C2 . C3 . H31 . 118.1 no
C4 . C3 . H31 . 119.8 no
C3 . C4 . C5 . 120.37(16) yes
C3 . C4 . H41 . 121.4 no
C5 . C4 . H41 . 118.2 no
C4 . C5 . C6 . 118.28(15) yes
C4 . C5 . H51 . 121.7 no
C6 . C5 . H51 . 120.0 no
C1 . C6 . C5 . 121.13(14) yes
C1 . C6 . C7 . 107.87(13) yes
C5 . C6 . C7 . 130.99(14) yes
C6 . C7 . O1 . 127.43(13) yes
C6 . C7 . C8 . 105.40(12) yes
O1 . C7 . C8 . 126.80(13) yes
C7 . C8 . N1 . 107.26(12) yes
C7 . C8 . C9 . 130.18(13) yes
N1 . C8 . C9 . 121.64(12) yes
N2 . C9 . C8 . 127.52(12) yes
N2 . C9 . C10 . 107.77(11) yes
C8 . C9 . C10 . 124.49(12) yes
C9 . C10 . O3 . 109.58(11) yes
C9 . C10 . O2 . 114.13(12) yes
O3 . C10 . O2 . 106.41(11) yes
C9 . C10 . C11 . 102.68(11) yes
O3 . C10 . C11 . 113.54(11) yes
O2 . C10 . C11 . 110.69(11) yes
C10 . C11 . C12 . 128.32(13) yes
C10 . C11 . C16 . 109.54(12) yes
C12 . C11 . C16 . 122.01(13) yes
C11 . C12 . C13 . 117.90(14) yes
C11 . C12 . H121 . 120.1 no
C13 . C12 . H121 . 122.0 no
C12 . C13 . C14 . 119.94(15) yes
C12 . C13 . H131 . 117.6 no
C14 . C13 . H131 . 122.4 no
C13 . C14 . C15 . 122.28(15) yes
C13 . C14 . H141 . 120.2 no
C15 . C14 . H141 . 117.5 no
C14 . C15 . C16 . 117.26(15) yes
C14 . C15 . H151 . 124.2 no
C16 . C15 . H151 . 118.5 no
N2 . C16 . C15 . 129.69(14) yes
N2 . C16 . C11 . 109.63(12) yes
C15 . C16 . C11 . 120.60(14) yes
N1 . C17 . C18 . 113.68(13) yes
N1 . C17 . H171 . 107.8 no
C18 . C17 . H171 . 109.2 no
N1 . C17 . H172 . 110.5 no
C18 . C17 . H172 . 109.3 no
H171 . C17 . H172 . 106.0 no
C17 . C18 . O2 . 110.20(13) yes
C17 . C18 . C19 . 114.19(14) yes
O2 . C18 . C19 . 102.97(12) yes
C17 . C18 . H181 . 108.6 no
O2 . C18 . H181 . 107.9 no
C19 . C18 . H181 . 112.7 no
C18 . C19 . O3 . 104.31(12) yes
C18 . C19 . H191 . 111.4 no
O3 . C19 . H191 . 109.1 no
C18 . C19 . H192 . 111.5 no
O3 . C19 . H192 . 109.3 no
H191 . C19 . H192 . 111.1 no
N2 . C20 . C21 . 124.30(14) yes
N2 . C20 . H201 . 113.4 no
C21 . C20 . H201 . 122.3 no
C20 . C21 . C22 . 122.08(15) yes
C20 . C21 . H211 . 120.1 no
C22 . C21 . H211 . 117.8 no
C21 . C22 . O4 . 109.58(13) yes
C21 . C22 . H221 . 107.9 no
O4 . C22 . H221 . 110.0 no
C21 . C22 . H222 . 107.9 no
O4 . C22 . H222 . 111.3 no
H221 . C22 . H222 . 110.0 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
O4 . H1 . O1 2_556 178(2) 0.94(2) 1.80(2) 2.747(2) yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 O2 C10 O3 -36.22(14) . . . . no
C18 O2 C10 C9 84.75(14) . . . . no
C18 O2 C10 C11 -160.03(12) . . . . no
C10 O2 C18 C17 -86.49(14) . . . . no
C10 O2 C18 C19 35.70(14) . . . . no
C19 O3 C10 O2 21.44(14) . . . . no
C19 O3 C10 C9 -102.42(12) . . . . no
C19 O3 C10 C11 143.45(12) . . . . no
C10 O3 C19 C18 1.04(15) . . . . no
C8 N1 C1 C2 -175.84(16) . . . . no
C8 N1 C1 C6 4.33(17) . . . . no
C17 N1 C1 C2 -22.5(2) . . . . no
C17 N1 C1 C6 157.63(13) . . . . no
C1 N1 C8 C7 -5.13(15) . . . . no
C1 N1 C8 C9 -175.19(13) . . . . no
C17 N1 C8 C7 -157.29(13) . . . . no
C17 N1 C8 C9 32.6(2) . . . . no
C1 N1 C17 C18 147.70(14) . . . . no
C8 N1 C17 C18 -63.38(19) . . . . no
C16 N2 C9 C8 -177.54(14) . . . . no
C16 N2 C9 C10 -2.77(15) . . . . no
C20 N2 C9 C8 15.4(2) . . . . no
C20 N2 C9 C10 -169.79(12) . . . . no
C9 N2 C16 C11 3.16(16) . . . . no
C9 N2 C16 C15 -173.69(15) . . . . no
C20 N2 C16 C11 170.23(13) . . . . no
C20 N2 C16 C15 -6.6(2) . . . . no
C9 N2 C20 C21 -149.93(15) . . . . no
C16 N2 C20 C21 44.8(2) . . . . no
N1 C1 C2 C3 -179.33(16) . . . . no
C6 C1 C2 C3 0.5(2) . . . . no
N1 C1 C6 C5 179.52(14) . . . . no
N1 C1 C6 C7 -1.70(17) . . . . no
C2 C1 C6 C5 -0.3(2) . . . . no
C2 C1 C6 C7 178.45(14) . . . . no
C1 C2 C3 C4 -0.7(3) . . . . no
C2 C3 C4 C5 0.7(3) . . . . no
C3 C4 C5 C6 -0.5(3) . . . . no
C4 C5 C6 C1 0.3(2) . . . . no
C4 C5 C6 C7 -178.14(16) . . . . no
C1 C6 C7 O1 171.87(14) . . . . no
C1 C6 C7 C8 -1.48(16) . . . . no
C5 C6 C7 O1 -9.5(3) . . . . no
C5 C6 C7 C8 177.14(15) . . . . no
O1 C7 C8 N1 -169.40(14) . . . . no
O1 C7 C8 C9 -0.5(3) . . . . no
C6 C7 C8 N1 4.00(15) . . . . no
C6 C7 C8 C9 172.91(15) . . . . no
N1 C8 C9 N2 -170.20(13) . . . . no
N1 C8 C9 C10 15.9(2) . . . . no
C7 C8 C9 N2 22.3(2) . . . . no
C7 C8 C9 C10 -151.69(14) . . . . no
N2 C9 C10 O2 121.26(12) . . . . no
N2 C9 C10 O3 -119.54(12) . . . . no
N2 C9 C10 C11 1.43(14) . . . . no
C8 C9 C10 O2 -63.78(18) . . . . no
C8 C9 C10 O3 55.42(17) . . . . no
C8 C9 C10 C11 176.39(13) . . . . no
O2 C10 C11 C12 54.01(19) . . . . no
O2 C10 C11 C16 -121.74(13) . . . . no
O3 C10 C11 C12 -65.59(19) . . . . no
O3 C10 C11 C16 118.66(13) . . . . no
C9 C10 C11 C12 176.21(14) . . . . no
C9 C10 C11 C16 0.46(15) . . . . no
C10 C11 C12 C13 -175.25(14) . . . . no
C16 C11 C12 C13 0.0(2) . . . . no
C10 C11 C16 N2 -2.13(16) . . . . no
C10 C11 C16 C15 175.04(14) . . . . no
C12 C11 C16 N2 -178.21(13) . . . . no
C12 C11 C16 C15 -1.0(2) . . . . no
C11 C12 C13 C14 0.9(2) . . . . no
C12 C13 C14 C15 -0.8(3) . . . . no
C13 C14 C15 C16 -0.2(3) . . . . no
C14 C15 C16 N2 177.62(15) . . . . no
C14 C15 C16 C11 1.1(2) . . . . no
N1 C17 C18 O2 77.79(16) . . . . no
N1 C17 C18 C19 -37.51(19) . . . . no
O2 C18 C19 O3 -22.24(15) . . . . no
C17 C18 C19 O3 97.22(15) . . . . no
N2 C20 C21 C22 -177.28(14) . . . . no
C20 C21 C22 O4 -112.64(16) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 N2 3.2006(16) . . no
O1 C20 2.7598(18) . . no
O1 C21 3.3786(18) . . no
O1 C18 3.2963(19) . 3_646 no
O1 O4 2.7468(15) . 2_456 no
O1 C19 3.364(2) . 3_646 no
O2 C14 3.317(2) . 3_756 no
O2 N1 3.0983(16) . . no
O3 C17 3.3927(18) . 3_646 no
O3 N1 3.1390(16) . . no
O4 O1 2.7468(15) . 2_556 no
C3 C6 3.563(2) . 2_466 no
C4 C20 3.327(2) . 1_455 no
C7 C20 3.164(2) . . no
C8 C19 3.401(2) . . no
C15 C21 3.169(2) . . no
C19 C21 3.465(2) . 3_656 no

_iucr_refine_instruction_details_constraints 
;
#
# Punched on 06/12/16 at 12:15:18
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S H(1,X'S) 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 06/12/16 at 12:15:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
