# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1584403'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;

_exptl_crystal_recrystallization_method 
; 
 
;

#see the bottom part of the file for the full list of the applied restraints. 

#end of refcif 
_cell_length_a                   7.8954(8)
_cell_length_b                   22.637(2)
_cell_length_c                   11.6950(11)
_cell_angle_alpha                90
_cell_angle_beta                 90.952(7)
_cell_angle_gamma                90
_cell_volume                     2089.9(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P n'
_symmetry_space_group_name_Hall  'P -2yac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
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 = C18 H32 N4 O4 
# Dc =      1.17 Fooo =    919.99 Mu =      6.79 M =    736.95
# Found Formula = C18 H38 N4 O7 
# Dc =      1.34 FOOO =    919.99 Mu =      8.54 M =    845.04

_chemical_formula_sum            'C18 H38 N4 O7'
_chemical_formula_moiety         '2(C9 H16 N2 O2), 3(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         422.52


_cell_measurement_reflns_used    2197
_cell_measurement_theta_min      4
_cell_measurement_theta_max      67
_cell_measurement_temperature    123

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.020
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.180

_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             919.991
_exptl_absorpt_coefficient_mu    0.854

# Sheldrick geometric approximatio 0.91 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            15770
_reflns_number_total             6655
_diffrn_reflns_av_R_equivalents  0.070
# Number of reflections without Friedels Law is 6655 
# Number of reflections with Friedels Law is 3583 
# Theoretical number of reflections is about 3879 


_diffrn_reflns_theta_min         3.905
_diffrn_reflns_theta_max         68.901
_diffrn_measured_fraction_theta_max 0.957

_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_full 0.984


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              -12
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.25
_refine_diff_density_max         0.27


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>1.0\s(I)
_refine_ls_number_reflns         5647
_refine_ls_number_restraints     42
_refine_ls_number_parameters     584
_oxford_refine_ls_R_factor_ref   0.0542
_refine_ls_wR_factor_ref         0.0519
_refine_ls_goodness_of_fit_ref   1.1157
_refine_ls_shift/su_max          0.0004738
_refine_ls_shift/su_mean         0.0000335


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        6623
_refine_ls_R_factor_all          0.0692
_refine_ls_wR_factor_all         0.0773

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                4743
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_gt          0.0473

_refine_ls_abs_structure_Flack   0.7(2)
_refine_ls_abs_structure_details 'Flack (1983), 3072 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 F
_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: 
 0.284 0.255 0.127 
;

# start Validation Reply Form
_vrf_PLAT962_I                   
;
PROBLEM: Number of Input Relections with Sigma(Fo\^2) =  0          5       
RESPONSE: Careful testing showed that none of the sigmas are zero
;
# end Validation Reply Form

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.6647(4) 0.34285(12) 0.3574(3) 0.0174 1.0000 Uani D . . . . .
N2 N 0.7266(3) 0.21290(12) 0.5598(2) 0.0129 1.0000 Uani D . . . . .
O1 O 0.4457(3) 0.39253(11) 0.4371(2) 0.0232 1.0000 Uani . . . . . .
O2 O 0.6059(3) 0.43668(10) 0.3040(2) 0.0195 1.0000 Uani . . . . . .
C1 C 0.5687(4) 0.39293(16) 0.3670(3) 0.0178 1.0000 Uani D . . . . .
C2 C 0.6319(4) 0.28669(15) 0.4142(3) 0.0157 1.0000 Uani D . . . . .
C3 C 0.7707(4) 0.27207(14) 0.5019(3) 0.0156 1.0000 Uani D . . . . .
C4 C 0.7811(5) 0.31581(16) 0.6025(3) 0.0219 1.0000 Uani . . . . . .
C5 C 0.8226(5) 0.27781(16) 0.7070(3) 0.0210 1.0000 Uani . . . . . .
C6 C 0.7092(5) 0.22423(17) 0.6847(3) 0.0196 1.0000 Uani D . . . . .
C7 C 0.8632(5) 0.16874(16) 0.5317(3) 0.0218 1.0000 Uani D . . . . .
C8 C 0.9406(5) 0.19348(17) 0.4245(3) 0.0253 1.0000 Uani . . . . . .
C9 C 0.9421(4) 0.25948(16) 0.4464(3) 0.0188 1.0000 Uani . . . . . .
H1 H 0.732(4) 0.3418(9) 0.302(2) 0.0212 1.0000 Uiso D . . . . .
H2 H 0.629(2) 0.1986(9) 0.5309(18) 0.0196 1.0000 Uiso D . . . . .
H21 H 0.5234 0.2872 0.4519 0.0177 1.0000 Uiso R . . . . .
H22 H 0.6298 0.2552 0.3577 0.0175 1.0000 Uiso R . . . . .
H41 H 0.8701 0.3449 0.5915 0.0278 1.0000 Uiso R . . . . .
H42 H 0.6737 0.3354 0.6095 0.0271 1.0000 Uiso R . . . . .
H51 H 0.7964 0.2969 0.7791 0.0250 1.0000 Uiso R . . . . .
H52 H 0.9414 0.2669 0.7075 0.0252 1.0000 Uiso R . . . . .
H61 H 0.5927 0.2335 0.7028 0.0233 1.0000 Uiso R . . . . .
H62 H 0.7476 0.1902 0.7298 0.0236 1.0000 Uiso R . . . . .
H71 H 0.9464 0.1668 0.5947 0.0243 1.0000 Uiso R . . . . .
H72 H 0.8134 0.1299 0.5193 0.0252 1.0000 Uiso R . . . . .
H81 H 0.8714 0.1838 0.3573 0.0301 1.0000 Uiso R . . . . .
H82 H 1.0530 0.1787 0.4142 0.0305 1.0000 Uiso R . . . . .
H91 H 0.9510 0.2820 0.3765 0.0218 1.0000 Uiso R . . . . .
H92 H 1.0347 0.2696 0.4984 0.0218 1.0000 Uiso R . . . . .
N3 N 0.3157(4) 0.57536(13) 0.5955(3) 0.0201 1.0000 Uani D . . . . .
N4 N 0.1952(4) 0.46291(12) 0.3692(2) 0.0145 1.0000 Uani D . . . . .
O3 O 0.5503(3) 0.61872(11) 0.5192(2) 0.0241 1.0000 Uani . . . . . .
O4 O 0.4156(3) 0.66147(11) 0.6658(2) 0.0230 1.0000 Uani . . . . . .
C10 C 0.4316(4) 0.62042(15) 0.5923(3) 0.0188 1.0000 Uani D . . . . .
C11 C 0.3222(4) 0.52265(15) 0.5276(3) 0.0166 1.0000 Uani D . . . . .
C12 C 0.1804(4) 0.52112(14) 0.4362(3) 0.0143 1.0000 Uani D . . . . .
C13 C 0.1922(4) 0.56912(16) 0.3439(3) 0.0187 1.0000 Uani . . . . . .
C14 C 0.1310(5) 0.53860(17) 0.2365(3) 0.0225 1.0000 Uani . . . . . .
C15 C 0.2152(5) 0.47895(16) 0.2453(3) 0.0196 1.0000 Uani D . . . . .
C16 C 0.0384(5) 0.42629(15) 0.3911(3) 0.0208 1.0000 Uani D . . . . .
C17 C -0.0289(5) 0.45111(16) 0.5008(3) 0.0204 1.0000 Uani . . . . . .
C18 C 0.0042(4) 0.51697(15) 0.4905(3) 0.0162 1.0000 Uani . . . . . .
H3 H 0.253(4) 0.5737(11) 0.656(2) 0.0247 1.0000 Uiso D . . . . .
H4 H 0.288(2) 0.4423(9) 0.3919(18) 0.0214 1.0000 Uiso D . . . . .
H111 H 0.4305 0.5205 0.4892 0.0193 1.0000 Uiso R . . . . .
H112 H 0.3121 0.4884 0.5773 0.0187 1.0000 Uiso R . . . . .
H131 H 0.3077 0.5819 0.3360 0.0224 1.0000 Uiso R . . . . .
H132 H 0.1214 0.6030 0.3626 0.0226 1.0000 Uiso R . . . . .
H141 H 0.1677 0.5596 0.1689 0.0251 1.0000 Uiso R . . . . .
H142 H 0.0097 0.5351 0.2369 0.0262 1.0000 Uiso R . . . . .
H151 H 0.3356 0.4820 0.2280 0.0239 1.0000 Uiso R . . . . .
H152 H 0.1672 0.4492 0.1947 0.0238 1.0000 Uiso R . . . . .
H161 H -0.0447 0.4320 0.3293 0.0251 1.0000 Uiso R . . . . .
H162 H 0.0673 0.3849 0.3961 0.0252 1.0000 Uiso R . . . . .
H171 H -0.1483 0.4435 0.5092 0.0242 1.0000 Uiso R . . . . .
H172 H 0.0313 0.4347 0.5665 0.0242 1.0000 Uiso R . . . . .
H181 H 0.0047 0.5363 0.5660 0.0190 1.0000 Uiso R . . . . .
H182 H -0.0796 0.5344 0.4390 0.0191 1.0000 Uiso R . . . . .
N5 N 0.5607(4) 0.81613(13) 0.3855(3) 0.0204 1.0000 Uani D . . . . .
N6 N 0.7714(4) 0.70779(13) 0.5898(3) 0.0165 1.0000 Uani D . . . . .
O5 O 0.3354(3) 0.84792(12) 0.4904(2) 0.0303 1.0000 Uani . . . . . .
O6 O 0.4139(3) 0.89648(11) 0.3322(2) 0.0273 1.0000 Uani . . . . . .
C19 C 0.4286(5) 0.85482(16) 0.4062(3) 0.0212 1.0000 Uani D . . . . .
C20 C 0.5911(4) 0.76161(15) 0.4466(3) 0.0181 1.0000 Uani D . . . . .
C21 C 0.7514(4) 0.76681(15) 0.5233(3) 0.0155 1.0000 Uani D . . . . .
C22 C 0.7361(5) 0.81306(17) 0.6167(3) 0.0236 1.0000 Uani . . . . . .
C23 C 0.8263(5) 0.78621(18) 0.7195(3) 0.0272 1.0000 Uani . . . . . .
C24 C 0.7662(5) 0.72277(18) 0.7147(3) 0.0248 1.0000 Uani D . . . . .
C25 C 0.9359(5) 0.68045(16) 0.5556(4) 0.0275 1.0000 Uani D . . . . .
C26 C 0.9725(5) 0.70740(19) 0.4403(4) 0.0292 1.0000 Uani . . . . . .
C27 C 0.9146(5) 0.77028(16) 0.4540(3) 0.0218 1.0000 Uani . . . . . .
H5 H 0.618(4) 0.8219(12) 0.326(2) 0.0243 1.0000 Uiso D . . . . .
H6 H 0.689(3) 0.6834(9) 0.5707(18) 0.0251 1.0000 Uiso D . . . . .
H201 H 0.6074 0.7294 0.3924 0.0217 1.0000 Uiso R . . . . .
H202 H 0.4963 0.7531 0.4942 0.0226 1.0000 Uiso R . . . . .
H221 H 0.6175 0.8202 0.6335 0.0286 1.0000 Uiso R . . . . .
H222 H 0.7881 0.8494 0.5925 0.0283 1.0000 Uiso R . . . . .
H231 H 0.7932 0.8053 0.7904 0.0331 1.0000 Uiso R . . . . .
H232 H 0.9485 0.7892 0.7126 0.0328 1.0000 Uiso R . . . . .
H241 H 0.6506 0.7202 0.7423 0.0289 1.0000 Uiso R . . . . .
H242 H 0.8409 0.6966 0.7584 0.0291 1.0000 Uiso R . . . . .
H251 H 1.0242 0.6924 0.6106 0.0340 1.0000 Uiso R . . . . .
H252 H 0.9292 0.6373 0.5526 0.0344 1.0000 Uiso R . . . . .
H261 H 0.9102 0.6871 0.3799 0.0354 1.0000 Uiso R . . . . .
H262 H 1.0930 0.7051 0.4248 0.0353 1.0000 Uiso R . . . . .
H271 H 0.9987 0.7930 0.4960 0.0259 1.0000 Uiso R . . . . .
H272 H 0.8931 0.7887 0.3802 0.0251 1.0000 Uiso R . . . . .
N7 N 0.2888(4) 1.08142(13) 0.4710(3) 0.0211 1.0000 Uani D . . . . .
N8 N 0.1381(4) 0.95633(13) 0.2805(3) 0.0172 1.0000 Uani D . . . . .
O7 O 0.5400(3) 1.10509(12) 0.3883(2) 0.0281 1.0000 Uani . . . . . .
O8 O 0.4289(3) 1.16451(11) 0.5202(2) 0.0232 1.0000 Uani . . . . . .
C28 C 0.4273(4) 1.11780(16) 0.4579(3) 0.0194 1.0000 Uani D . . . . .
C29 C 0.2781(5) 1.02288(16) 0.4225(3) 0.0210 1.0000 Uani D . . . . .
C30 C 0.1242(5) 1.01699(15) 0.3401(3) 0.0178 1.0000 Uani D . . . . .
C31 C 0.1263(5) 1.06173(17) 0.2436(3) 0.0252 1.0000 Uani . . . . . .
C32 C 0.0656(5) 1.02718(19) 0.1396(3) 0.0265 1.0000 Uani . . . . . .
C33 C 0.1558(5) 0.96857(18) 0.1553(3) 0.0268 1.0000 Uani D . . . . .
C34 C -0.0161(5) 0.92086(17) 0.3078(4) 0.0283 1.0000 Uani D . . . . .
C35 C -0.0770(5) 0.9481(2) 0.4180(4) 0.0337 1.0000 Uani . . . . . .
C36 C -0.0466(5) 1.01367(18) 0.4015(3) 0.0250 1.0000 Uani . . . . . .
H7 H 0.229(4) 1.0874(11) 0.532(2) 0.0252 1.0000 Uiso D . . . . .
H8 H 0.230(2) 0.9376(9) 0.3054(18) 0.0254 1.0000 Uiso D . . . . .
H291 H 0.3803 1.0167 0.3796 0.0250 1.0000 Uiso R . . . . .
H292 H 0.2697 0.9932 0.4825 0.0248 1.0000 Uiso R . . . . .
H311 H 0.2400 1.0774 0.2340 0.0299 1.0000 Uiso R . . . . .
H312 H 0.0508 1.0944 0.2607 0.0304 1.0000 Uiso R . . . . .
H321 H 0.0974 1.0468 0.0695 0.0320 1.0000 Uiso R . . . . .
H322 H -0.0566 1.0227 0.1396 0.0325 1.0000 Uiso R . . . . .
H331 H 0.2746 0.9710 0.1363 0.0343 1.0000 Uiso R . . . . .
H332 H 0.1037 0.9373 0.1096 0.0343 1.0000 Uiso R . . . . .
H341 H 0.0116 0.8796 0.3154 0.0333 1.0000 Uiso R . . . . .
H342 H -0.1021 0.9253 0.2475 0.0329 1.0000 Uiso R . . . . .
H351 H -0.0129 0.9334 0.4829 0.0405 1.0000 Uiso R . . . . .
H352 H -0.1970 0.9399 0.4273 0.0414 1.0000 Uiso R . . . . .
H361 H -0.1335 1.0312 0.3542 0.0289 1.0000 Uiso R . . . . .
H362 H -0.0407 1.0340 0.4743 0.0291 1.0000 Uiso R . . . . .
O9 O 0.6581(4) 0.56380(12) 0.3061(2) 0.0274 1.0000 Uani D . . . . .
H9 H 0.645(6) 0.5280(10) 0.321(4) 0.0420 1.0000 Uiso D . . . . .
H10 H 0.645(6) 0.578(2) 0.370(2) 0.0422 1.0000 Uiso D . . . . .
O10 O 0.7952(5) 0.65243(14) 0.1434(3) 0.0422 1.0000 Uani D . . . . .
H11 H 0.755(7) 0.6231(17) 0.177(4) 0.0631 1.0000 Uiso D . . . . .
H12 H 0.831(7) 0.635(2) 0.087(3) 0.0635 1.0000 Uiso D . . . . .
O11 O 0.7434(4) 0.77772(13) 0.1785(3) 0.0301 1.0000 Uani D . . . . .
H13 H 0.751(6) 0.7409(9) 0.167(4) 0.0450 1.0000 Uiso D . . . . .
H14 H 0.776(6) 0.797(2) 0.123(3) 0.0452 1.0000 Uiso D . . . . .
O12 O 0.2577(4) 0.77104(14) 0.6626(3) 0.0360 1.0000 Uani D . . . . .
H15 H 0.294(7) 0.7366(12) 0.648(5) 0.0552 1.0000 Uiso D . . . . .
H16 H 0.276(7) 0.795(2) 0.609(3) 0.0549 1.0000 Uiso D . . . . .
O13 O 0.1415(5) 0.92224(15) 0.6728(3) 0.0451 1.0000 Uani D . . . . .
H17 H 0.193(7) 0.8935(18) 0.647(5) 0.0680 1.0000 Uiso D . . . . .
H18 H 0.110(7) 0.906(2) 0.732(3) 0.0682 1.0000 Uiso D . . . . .
O14 O 0.1091(4) 1.04791(14) 0.6753(3) 0.0350 1.0000 Uani D . . . . .
H19 H 0.109(7) 1.0108(9) 0.682(5) 0.0529 1.0000 Uiso D . . . . .
H20 H 0.066(6) 1.064(2) 0.732(3) 0.0528 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1204(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.370(4) yes
N1 . C2 . 1.460(4) yes
N1 . H1 . 0.845(18) no
N2 . C3 . 1.543(4) yes
N2 . C6 . 1.492(5) yes
N2 . C7 . 1.511(4) yes
N2 . H2 . 0.896(18) no
O1 . C1 . 1.281(4) yes
O2 . C1 . 1.272(4) yes
C2 . C3 . 1.525(5) yes
C2 . H21 . 0.971 no
C2 . H22 . 0.971 no
C3 . C4 . 1.539(5) yes
C3 . C9 . 1.537(5) yes
C4 . C5 . 1.525(5) yes
C4 . H41 . 0.973 no
C4 . H42 . 0.961 no
C5 . C6 . 1.527(5) yes
C5 . H51 . 0.973 no
C5 . H52 . 0.970 no
C6 . H61 . 0.970 no
C6 . H62 . 0.980 no
C7 . C8 . 1.511(5) yes
C7 . H71 . 0.979 no
C7 . H72 . 0.972 no
C8 . C9 . 1.516(5) yes
C8 . H81 . 0.975 no
C8 . H82 . 0.958 no
C9 . H91 . 0.966 no
C9 . H92 . 0.971 no
N3 . C10 . 1.371(4) yes
N3 . C11 . 1.435(4) yes
N3 . H3 . 0.867(18) no
N4 . C12 . 1.538(4) yes
N4 . C15 . 1.505(5) yes
N4 . C16 . 1.516(4) yes
N4 . H4 . 0.902(18) no
O3 . C10 . 1.279(4) yes
O4 . C10 . 1.274(4) yes
C11 . C12 . 1.535(5) yes
C11 . H111 . 0.973 no
C11 . H112 . 0.973 no
C12 . C13 . 1.536(5) yes
C12 . C18 . 1.542(5) yes
C13 . C14 . 1.506(5) yes
C13 . H131 . 0.963 no
C13 . H132 . 0.975 no
C14 . C15 . 1.508(5) yes
C14 . H141 . 0.971 no
C14 . H142 . 0.961 no
C15 . H151 . 0.977 no
C15 . H152 . 0.969 no
C16 . C17 . 1.505(5) yes
C16 . H161 . 0.976 no
C16 . H162 . 0.966 no
C17 . C18 . 1.519(5) yes
C17 . H171 . 0.965 no
C17 . H172 . 0.971 no
C18 . H181 . 0.985 no
C18 . H182 . 0.972 no
N5 . C19 . 1.386(5) yes
N5 . C20 . 1.444(4) yes
N5 . H5 . 0.847(18) no
N6 . C21 . 1.552(4) yes
N6 . C24 . 1.501(5) yes
N6 . C25 . 1.499(5) yes
N6 . H6 . 0.877(18) no
O5 . C19 . 1.249(5) yes
O6 . C19 . 1.284(5) yes
C20 . C21 . 1.544(5) yes
C20 . H201 . 0.976 no
C20 . H202 . 0.960 no
C21 . C22 . 1.519(5) yes
C21 . C27 . 1.535(5) yes
C22 . C23 . 1.514(6) yes
C22 . H221 . 0.974 no
C22 . H222 . 0.963 no
C23 . C24 . 1.513(6) yes
C23 . H231 . 0.974 no
C23 . H232 . 0.972 no
C24 . H241 . 0.975 no
C24 . H242 . 0.974 no
C25 . C26 . 1.512(6) yes
C25 . H251 . 0.979 no
C25 . H252 . 0.978 no
C26 . C27 . 1.504(5) yes
C26 . H261 . 0.970 no
C26 . H262 . 0.973 no
C27 . H271 . 0.968 no
C27 . H272 . 0.971 no
N7 . C28 . 1.380(5) yes
N7 . C29 . 1.443(5) yes
N7 . H7 . 0.867(18) no
N8 . C30 . 1.545(4) yes
N8 . C33 . 1.499(5) yes
N8 . C34 . 1.498(5) yes
N8 . H8 . 0.889(18) no
O7 . C28 . 1.249(4) yes
O8 . C28 . 1.284(4) yes
C29 . C30 . 1.544(5) yes
C29 . H291 . 0.967 no
C29 . H292 . 0.974 no
C30 . C31 . 1.517(5) yes
C30 . C36 . 1.540(5) yes
C31 . C32 . 1.517(6) yes
C31 . H311 . 0.973 no
C31 . H312 . 0.972 no
C32 . C33 . 1.516(6) yes
C32 . H321 . 0.970 no
C32 . H322 . 0.970 no
C33 . H331 . 0.969 no
C33 . H332 . 0.974 no
C34 . C35 . 1.514(6) yes
C34 . H341 . 0.962 no
C34 . H342 . 0.976 no
C35 . C36 . 1.517(6) yes
C35 . H351 . 0.964 no
C35 . H352 . 0.973 no
C36 . H361 . 0.960 no
C36 . H362 . 0.968 no
O9 . H9 . 0.836(19) no
O9 . H10 . 0.820(19) no
O10 . H11 . 0.835(19) no
O10 . H12 . 0.823(19) no
O11 . H13 . 0.848(19) no
O11 . H14 . 0.824(19) no
O12 . H15 . 0.849(19) no
O12 . H16 . 0.843(19) no
O13 . H17 . 0.829(19) no
O13 . H18 . 0.823(19) no
O14 . H19 . 0.844(19) no
O14 . H20 . 0.835(19) 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
C1 . N1 . C2 . 125.5(3) yes
C1 . N1 . H1 . 116.3(13) no
C2 . N1 . H1 . 116.3(13) no
C3 . N2 . C6 . 107.8(3) yes
C3 . N2 . C7 . 108.2(2) yes
C6 . N2 . C7 . 113.8(3) yes
C3 . N2 . H2 . 110.3(14) no
C6 . N2 . H2 . 109.8(14) no
C7 . N2 . H2 . 106.9(14) no
N1 . C1 . O1 . 118.3(3) yes
N1 . C1 . O2 . 117.6(3) yes
O1 . C1 . O2 . 124.1(3) yes
N1 . C2 . C3 . 111.4(3) yes
N1 . C2 . H21 . 111.2 no
C3 . C2 . H21 . 109.0 no
N1 . C2 . H22 . 109.3 no
C3 . C2 . H22 . 107.6 no
H21 . C2 . H22 . 108.2 no
N2 . C3 . C2 . 108.6(3) yes
N2 . C3 . C4 . 103.5(3) yes
C2 . C3 . C4 . 113.8(3) yes
N2 . C3 . C9 . 103.3(3) yes
C2 . C3 . C9 . 112.6(3) yes
C4 . C3 . C9 . 113.9(3) yes
C3 . C4 . C5 . 104.9(3) yes
C3 . C4 . H41 . 111.3 no
C5 . C4 . H41 . 110.0 no
C3 . C4 . H42 . 109.0 no
C5 . C4 . H42 . 111.8 no
H41 . C4 . H42 . 109.8 no
C4 . C5 . C6 . 101.2(3) yes
C4 . C5 . H51 . 113.5 no
C6 . C5 . H51 . 111.6 no
C4 . C5 . H52 . 110.1 no
C6 . C5 . H52 . 111.3 no
H51 . C5 . H52 . 109.1 no
C5 . C6 . N2 . 103.9(3) yes
C5 . C6 . H61 . 110.2 no
N2 . C6 . H61 . 110.8 no
C5 . C6 . H62 . 111.0 no
N2 . C6 . H62 . 111.1 no
H61 . C6 . H62 . 109.8 no
N2 . C7 . C8 . 103.6(3) yes
N2 . C7 . H71 . 109.8 no
C8 . C7 . H71 . 111.4 no
N2 . C7 . H72 . 110.0 no
C8 . C7 . H72 . 112.2 no
H71 . C7 . H72 . 109.7 no
C7 . C8 . C9 . 103.1(3) yes
C7 . C8 . H81 . 110.9 no
C9 . C8 . H81 . 111.1 no
C7 . C8 . H82 . 111.3 no
C9 . C8 . H82 . 111.2 no
H81 . C8 . H82 . 109.1 no
C3 . C9 . C8 . 104.5(3) yes
C3 . C9 . H91 . 109.7 no
C8 . C9 . H91 . 112.1 no
C3 . C9 . H92 . 110.6 no
C8 . C9 . H92 . 110.0 no
H91 . C9 . H92 . 109.9 no
C10 . N3 . C11 . 125.0(3) yes
C10 . N3 . H3 . 116.2(13) no
C11 . N3 . H3 . 116.1(13) no
C12 . N4 . C15 . 107.1(3) yes
C12 . N4 . C16 . 108.2(2) yes
C15 . N4 . C16 . 113.2(3) yes
C12 . N4 . H4 . 111.1(14) no
C15 . N4 . H4 . 108.1(14) no
C16 . N4 . H4 . 109.1(14) no
N3 . C10 . O3 . 119.5(3) yes
N3 . C10 . O4 . 116.8(3) yes
O3 . C10 . O4 . 123.7(3) yes
N3 . C11 . C12 . 111.8(3) yes
N3 . C11 . H111 . 109.7 no
C12 . C11 . H111 . 108.3 no
N3 . C11 . H112 . 109.1 no
C12 . C11 . H112 . 109.4 no
H111 . C11 . H112 . 108.5 no
N4 . C12 . C11 . 108.2(3) yes
N4 . C12 . C13 . 104.0(3) yes
C11 . C12 . C13 . 114.9(3) yes
N4 . C12 . C18 . 103.6(3) yes
C11 . C12 . C18 . 111.5(3) yes
C13 . C12 . C18 . 113.5(3) yes
C12 . C13 . C14 . 103.8(3) yes
C12 . C13 . H131 . 110.4 no
C14 . C13 . H131 . 110.5 no
C12 . C13 . H132 . 110.9 no
C14 . C13 . H132 . 111.8 no
H131 . C13 . H132 . 109.4 no
C13 . C14 . C15 . 102.6(3) yes
C13 . C14 . H141 . 111.0 no
C15 . C14 . H141 . 110.9 no
C13 . C14 . H142 . 109.8 no
C15 . C14 . H142 . 111.4 no
H141 . C14 . H142 . 110.8 no
C14 . C15 . N4 . 103.2(3) yes
C14 . C15 . H151 . 110.7 no
N4 . C15 . H151 . 109.5 no
C14 . C15 . H152 . 114.4 no
N4 . C15 . H152 . 112.0 no
H151 . C15 . H152 . 107.1 no
N4 . C16 . C17 . 103.9(3) yes
N4 . C16 . H161 . 110.0 no
C17 . C16 . H161 . 109.8 no
N4 . C16 . H162 . 110.4 no
C17 . C16 . H162 . 113.4 no
H161 . C16 . H162 . 109.2 no
C16 . C17 . C18 . 103.6(3) yes
C16 . C17 . H171 . 112.3 no
C18 . C17 . H171 . 110.7 no
C16 . C17 . H172 . 111.0 no
C18 . C17 . H172 . 110.8 no
H171 . C17 . H172 . 108.5 no
C12 . C18 . C17 . 104.5(3) yes
C12 . C18 . H181 . 110.6 no
C17 . C18 . H181 . 111.3 no
C12 . C18 . H182 . 109.2 no
C17 . C18 . H182 . 109.4 no
H181 . C18 . H182 . 111.6 no
C19 . N5 . C20 . 124.9(3) yes
C19 . N5 . H5 . 117.3(13) no
C20 . N5 . H5 . 117.0(13) no
C21 . N6 . C24 . 106.8(3) yes
C21 . N6 . C25 . 107.6(3) yes
C24 . N6 . C25 . 113.0(3) yes
C21 . N6 . H6 . 110.3(14) no
C24 . N6 . H6 . 111.0(14) no
C25 . N6 . H6 . 108.1(14) no
N5 . C19 . O6 . 113.9(3) yes
N5 . C19 . O5 . 120.9(3) yes
O6 . C19 . O5 . 125.2(3) yes
N5 . C20 . C21 . 110.5(3) yes
N5 . C20 . H201 . 109.8 no
C21 . C20 . H201 . 108.6 no
N5 . C20 . H202 . 109.4 no
C21 . C20 . H202 . 108.6 no
H201 . C20 . H202 . 109.9 no
C20 . C21 . N6 . 107.5(3) yes
C20 . C21 . C22 . 113.3(3) yes
N6 . C21 . C22 . 104.0(3) yes
C20 . C21 . C27 . 112.6(3) yes
N6 . C21 . C27 . 103.3(3) yes
C22 . C21 . C27 . 114.9(3) yes
C21 . C22 . C23 . 104.6(3) yes
C21 . C22 . H221 . 110.4 no
C23 . C22 . H221 . 110.3 no
C21 . C22 . H222 . 109.7 no
C23 . C22 . H222 . 112.3 no
H221 . C22 . H222 . 109.5 no
C22 . C23 . C24 . 102.1(3) yes
C22 . C23 . H231 . 111.7 no
C24 . C23 . H231 . 111.3 no
C22 . C23 . H232 . 111.1 no
C24 . C23 . H232 . 112.0 no
H231 . C23 . H232 . 108.7 no
C23 . C24 . N6 . 103.7(3) yes
C23 . C24 . H241 . 109.8 no
N6 . C24 . H241 . 110.4 no
C23 . C24 . H242 . 111.8 no
N6 . C24 . H242 . 110.3 no
H241 . C24 . H242 . 110.7 no
N6 . C25 . C26 . 104.5(3) yes
N6 . C25 . H251 . 108.8 no
C26 . C25 . H251 . 109.2 no
N6 . C25 . H252 . 112.0 no
C26 . C25 . H252 . 112.4 no
H251 . C25 . H252 . 109.7 no
C25 . C26 . C27 . 102.9(3) yes
C25 . C26 . H261 . 110.9 no
C27 . C26 . H261 . 112.0 no
C25 . C26 . H262 . 110.3 no
C27 . C26 . H262 . 111.8 no
H261 . C26 . H262 . 108.9 no
C21 . C27 . C26 . 105.5(3) yes
C21 . C27 . H271 . 109.5 no
C26 . C27 . H271 . 110.5 no
C21 . C27 . H272 . 110.8 no
C26 . C27 . H272 . 111.1 no
H271 . C27 . H272 . 109.3 no
C28 . N7 . C29 . 123.1(3) yes
C28 . N7 . H7 . 116.0(14) no
C29 . N7 . H7 . 115.8(14) no
C30 . N8 . C33 . 106.6(3) yes
C30 . N8 . C34 . 108.4(3) yes
C33 . N8 . C34 . 113.4(3) yes
C30 . N8 . H8 . 109.9(14) no
C33 . N8 . H8 . 108.7(14) no
C34 . N8 . H8 . 109.8(14) no
N7 . C28 . O8 . 115.4(3) yes
N7 . C28 . O7 . 120.6(3) yes
O8 . C28 . O7 . 124.0(3) yes
N7 . C29 . C30 . 111.4(3) yes
N7 . C29 . H291 . 107.0 no
C30 . C29 . H291 . 108.6 no
N7 . C29 . H292 . 110.7 no
C30 . C29 . H292 . 109.1 no
H291 . C29 . H292 . 110.0 no
C29 . C30 . N8 . 107.3(3) yes
C29 . C30 . C31 . 112.9(3) yes
N8 . C30 . C31 . 104.8(3) yes
C29 . C30 . C36 . 113.6(3) yes
N8 . C30 . C36 . 103.7(3) yes
C31 . C30 . C36 . 113.6(3) yes
C30 . C31 . C32 . 104.2(3) yes
C30 . C31 . H311 . 110.5 no
C32 . C31 . H311 . 112.0 no
C30 . C31 . H312 . 109.9 no
C32 . C31 . H312 . 111.7 no
H311 . C31 . H312 . 108.5 no
C31 . C32 . C33 . 102.3(3) yes
C31 . C32 . H321 . 111.0 no
C33 . C32 . H321 . 112.1 no
C31 . C32 . H322 . 110.8 no
C33 . C32 . H322 . 111.9 no
H321 . C32 . H322 . 108.6 no
C32 . C33 . N8 . 103.2(3) yes
C32 . C33 . H331 . 112.2 no
N8 . C33 . H331 . 109.9 no
C32 . C33 . H332 . 112.1 no
N8 . C33 . H332 . 110.9 no
H331 . C33 . H332 . 108.5 no
N8 . C34 . C35 . 103.5(3) yes
N8 . C34 . H341 . 110.8 no
C35 . C34 . H341 . 113.0 no
N8 . C34 . H342 . 110.4 no
C35 . C34 . H342 . 110.3 no
H341 . C34 . H342 . 108.7 no
C34 . C35 . C36 . 103.7(3) yes
C34 . C35 . H351 . 111.0 no
C36 . C35 . H351 . 110.9 no
C34 . C35 . H352 . 110.0 no
C36 . C35 . H352 . 110.9 no
H351 . C35 . H352 . 110.2 no
C30 . C36 . C35 . 104.4(3) yes
C30 . C36 . H361 . 109.5 no
C35 . C36 . H361 . 111.3 no
C30 . C36 . H362 . 110.9 no
C35 . C36 . H362 . 111.0 no
H361 . C36 . H362 . 109.6 no
H9 . O9 . H10 . 100(5) no
H11 . O10 . H12 . 98(5) no
H13 . O11 . H14 . 112(5) no
H15 . O12 . H16 . 112(5) no
H17 . O13 . H18 . 97(6) no
H19 . O14 . H20 . 111(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
N1 . H1 . O4 2_564 177(3) 0.845 2.172 3.016(5) yes
N2 . H2 . O8 1_545 162(2) 0.896 1.761 2.627(5) yes
N2 . H2 . C28 1_545 155.4(18) 0.896 2.562 3.397(5) yes
C2 . H22 . O12 2_564 140.16(10) 0.971 2.580 3.383(5) yes
N3 . H3 . O2 2_465 176(3) 0.867 2.118 2.983(5) yes
N4 . H4 . O1 . 171(2) 0.902 1.757 2.651(5) yes
N4 . H4 . C1 . 155.4(18) 0.902 2.506 3.348(5) yes
C15 . H151 . O2 . 136.07(10) 0.977 2.517 3.291(5) yes
N5 . H5 . O11 . 144(3) 0.847 2.239 2.969(5) yes
N6 . H6 . O3 . 167.4(20) 0.877 1.921 2.783(5) yes
N6 . H6 . O4 . 130.7(17) 0.877 2.498 3.141(5) yes
N6 . H6 . C10 . 158.6(18) 0.877 2.502 3.333(5) yes
C23 . H232 . O12 1_655 164.16(12) 0.972 2.553 3.498(5) yes
C24 . H241 . O4 . 128.44(11) 0.975 2.440 3.140(5) yes
N7 . H7 . O14 . 146(2) 0.867 2.140 2.900(5) yes
N8 . H8 . O6 . 171(2) 0.889 1.745 2.626(5) yes
C33 . H332 . C28 2_474 162.58(13) 0.974 2.562 3.502(5) yes
C34 . H342 . O14 2_474 153.00(12) 0.976 2.493 3.392(5) yes
C35 . H351 . O13 . 164.69(13) 0.964 2.528 3.468(5) yes
O9 . H9 . O2 . 163(5) 0.836 2.098 2.907(5) yes
O9 . H10 . O3 . 166(5) 0.820 2.123 2.924(5) yes
O10 . H11 . O9 . 163(5) 0.835 2.172 2.981(5) yes
O10 . H12 . O1 2_564 169(6) 0.823 2.080 2.892(5) yes
O11 . H13 . O10 . 174(5) 0.848 2.051 2.896(5) yes
O11 . H14 . O8 2_574 160(5) 0.824 1.928 2.715(5) yes
O12 . H15 . O4 . 160(5) 0.849 1.963 2.776(5) yes
O12 . H16 . O5 . 175(5) 0.843 1.898 2.739(5) yes
O13 . H17 . O5 . 149(5) 0.829 2.396 3.136(5) yes
O13 . H18 . O7 2_475 162(6) 0.823 1.934 2.729(5) yes
O14 . H19 . O13 . 169(5) 0.844 2.024 2.856(5) yes
O14 . H20 . O6 2_475 163(5) 0.835 1.914 2.724(5) yes


####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1584404'
_audit_update_record             
;
2017-11-07 deposited with the CCDC.
2018-12-21 downloaded from the CCDC.
;

_exptl_crystal_recrystallization_method 
; 
 
;

#see the bottom part of the file for the full list of the applied restraints. 

#end of refcif 
_cell_length_a                   7.0751(5)
_cell_length_b                   16.6440(12)
_cell_length_c                   13.0818(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.578(2)
_cell_angle_gamma                90
_cell_volume                     1483.89(10)

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

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C11 H28 N2 O6 
# Dc =      1.27 Fooo =    624.00 Mu =      8.56 M =    284.35
# Found Formula = C11 H28 N2 O6 
# Dc =      1.27 FOOO =    624.00 Mu =      8.56 M =    284.35

_chemical_formula_sum            'C11 H28 N2 O6'
_chemical_formula_moiety         'C11 H20 N2 O2, 4(H2 O)'
_chemical_compound_source        ?
_chemical_formula_weight         284.35


_cell_measurement_reflns_used    6802
_cell_measurement_theta_min      4
_cell_measurement_theta_max      69
_cell_measurement_temperature    123

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.040
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_max          0.230

_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.856

# Sheldrick geometric approximatio 0.91 0.97 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.97
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      123
_diffrn_reflns_number            9721
_reflns_number_total             2692
_diffrn_reflns_av_R_equivalents  0.022
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2692 
# Theoretical number of reflections is about 5533 


_diffrn_reflns_theta_min         4.401
_diffrn_reflns_theta_max         69.119
_diffrn_measured_fraction_theta_max 0.971

_diffrn_reflns_theta_full        66.500
_diffrn_measured_fraction_theta_full 0.994


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              19
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.28


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


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>3.0\s(I)
_refine_ls_number_reflns         2629
_refine_ls_number_restraints     12
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0317
_refine_ls_wR_factor_ref         0.0346
_refine_ls_goodness_of_fit_ref   1.1204
_refine_ls_shift/su_max          0.0008146
_refine_ls_shift/su_mean         0.0002061


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2679
_refine_ls_R_factor_all          0.0322
_refine_ls_wR_factor_all         0.0360

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2644
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_gt          0.0347

# 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 F
_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: 
 0.138 0.110 0.322E-01 
;

# start Validation Reply Form
_vrf_PLAT962_I                   
;
PROBLEM: Number of Input Relections with Sigma(Fo\^2) =  0          6       
RESPONSE: Careful testing showed that none of the sigmas are zero
;
# end Validation Reply Form

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

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

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


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
N1 N 0.38559(11) 0.16645(5) 0.61502(6) 0.0145 1.0000 Uani . . . . . .
N2 N 0.77828(12) 0.25465(5) 0.40459(6) 0.0137 1.0000 Uani D . . . . .
O1 O 0.13969(9) 0.25375(4) 0.53952(5) 0.0168 1.0000 Uani . . . . . .
O2 O 0.07845(10) 0.12219(4) 0.53545(5) 0.0186 1.0000 Uani . . . . . .
C1 C 0.19362(13) 0.18104(5) 0.56124(7) 0.0131 1.0000 Uani . . . . . .
C2 C 0.45277(15) 0.08422(6) 0.64042(8) 0.0205 1.0000 Uani . . . . . .
C3 C 0.53435(13) 0.22937(6) 0.63678(7) 0.0142 1.0000 Uani . . . . . .
C4 C 0.68232(13) 0.22578(6) 0.57018(7) 0.0142 1.0000 Uani . . . . . .
C5 C 0.59994(13) 0.24564(5) 0.45197(7) 0.0132 1.0000 Uani D . . . . .
C6 C 0.49722(14) 0.32778(6) 0.43044(7) 0.0177 1.0000 Uani . . . . . .
C7 C 0.56014(15) 0.36192(6) 0.33606(8) 0.0208 1.0000 Uani . . . . . .
C8 C 0.77543(15) 0.33906(6) 0.36371(8) 0.0186 1.0000 Uani D . . . . .
C9 C 0.76245(15) 0.19095(6) 0.32075(7) 0.0181 1.0000 Uani D . . . . .
C10 C 0.63451(15) 0.12681(6) 0.35034(8) 0.0186 1.0000 Uani . . . . . .
C11 C 0.48255(14) 0.17649(6) 0.38579(7) 0.0165 1.0000 Uani . . . . . .
H1 H 0.8903(17) 0.2470(7) 0.4566(9) 0.0212 1.0000 Uiso D . . . . .
H21 H 0.4919 0.0590 0.5827 0.0330 1.0000 Uiso R . . . . .
H22 H 0.5654 0.0829 0.7022 0.0316 1.0000 Uiso R . . . . .
H23 H 0.3507 0.0538 0.6580 0.0314 1.0000 Uiso R . . . . .
H31 H 0.4666 0.2804 0.6277 0.0149 1.0000 Uiso R . . . . .
H32 H 0.6105 0.2251 0.7127 0.0163 1.0000 Uiso R . . . . .
H41 H 0.7435 0.1726 0.5768 0.0163 1.0000 Uiso R . . . . .
H42 H 0.7837 0.2649 0.5999 0.0169 1.0000 Uiso R . . . . .
H61 H 0.5451 0.3621 0.4909 0.0216 1.0000 Uiso R . . . . .
H62 H 0.3569 0.3215 0.4157 0.0204 1.0000 Uiso R . . . . .
H71 H 0.5430 0.4193 0.3297 0.0265 1.0000 Uiso R . . . . .
H72 H 0.4902 0.3367 0.2691 0.0237 1.0000 Uiso R . . . . .
H81 H 0.8503 0.3724 0.4206 0.0217 1.0000 Uiso R . . . . .
H82 H 0.8334 0.3400 0.3050 0.0217 1.0000 Uiso R . . . . .
H91 H 0.8948 0.1729 0.3228 0.0219 1.0000 Uiso R . . . . .
H92 H 0.6981 0.2149 0.2527 0.0215 1.0000 Uiso R . . . . .
H101 H 0.7133 0.0953 0.4091 0.0235 1.0000 Uiso R . . . . .
H102 H 0.5740 0.0921 0.2904 0.0221 1.0000 Uiso R . . . . .
H111 H 0.3857 0.1982 0.3244 0.0196 1.0000 Uiso R . . . . .
H112 H 0.4126 0.1455 0.4268 0.0196 1.0000 Uiso R . . . . .
O3 O 0.20535(11) 0.41492(4) 0.58298(6) 0.0207 1.0000 Uani D . . . . .
H2 H 0.194(2) 0.3651(8) 0.5719(11) 0.0317 1.0000 Uiso D . . . . .
H3 H 0.3185(19) 0.4216(8) 0.6218(11) 0.0335 1.0000 Uiso D . . . . .
O4 O -0.14274(12) 0.48832(6) 0.60050(7) 0.0322 1.0000 Uani D . . . . .
H4 H -0.038(2) 0.4666(9) 0.6008(13) 0.0474 1.0000 Uiso D . . . . .
H5 H -0.169(2) 0.5189(9) 0.5511(12) 0.0473 1.0000 Uiso D . . . . .
O5 O 0.11576(12) 0.00341(5) 0.39382(6) 0.0254 1.0000 Uani D . . . . .
H6 H 0.110(2) 0.0389(8) 0.4362(11) 0.0381 1.0000 Uiso D . . . . .
H7 H 0.050(2) -0.0353(8) 0.4053(12) 0.0382 1.0000 Uiso D . . . . .
O6 O 0.08635(11) 0.07090(5) 0.19976(6) 0.0239 1.0000 Uani D . . . . .
H8 H 0.099(2) 0.0503(9) 0.2571(10) 0.0366 1.0000 Uiso D . . . . .
H9 H 0.171(2) 0.0512(9) 0.1751(12) 0.0366 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1786(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 . C1 . 1.3731(12) yes
N1 . C2 . 1.4576(12) yes
N1 . C3 . 1.4577(12) yes
N2 . C5 . 1.5553(12) yes
N2 . C8 . 1.5015(12) yes
N2 . C9 . 1.5079(12) yes
N2 . H1 . 0.904(11) no
O1 . C1 . 1.2778(11) yes
O2 . C1 . 1.2608(11) yes
C2 . H21 . 0.967 no
C2 . H22 . 0.971 no
C2 . H23 . 0.960 no
C3 . C4 . 1.5325(12) yes
C3 . H31 . 0.966 no
C3 . H32 . 0.998 no
C4 . C5 . 1.5349(12) yes
C4 . H41 . 0.978 no
C4 . H42 . 0.969 no
C5 . C6 . 1.5384(13) yes
C5 . C11 . 1.5420(12) yes
C6 . C7 . 1.5299(14) yes
C6 . H61 . 0.960 no
C6 . H62 . 0.965 no
C7 . C8 . 1.5165(14) yes
C7 . H71 . 0.964 no
C7 . H72 . 0.977 no
C8 . H81 . 0.965 no
C8 . H82 . 0.963 no
C9 . C10 . 1.5156(14) yes
C9 . H91 . 0.977 no
C9 . H92 . 0.970 no
C10 . C11 . 1.5240(14) yes
C10 . H101 . 0.972 no
C10 . H102 . 0.976 no
C11 . H111 . 0.974 no
C11 . H112 . 0.971 no
O3 . H2 . 0.842(12) no
O3 . H3 . 0.832(13) no
O4 . H4 . 0.821(13) no
O4 . H5 . 0.805(13) no
O5 . H6 . 0.820(13) no
O5 . H7 . 0.833(13) no
O6 . H8 . 0.808(12) no
O6 . H9 . 0.818(13) 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
C1 . N1 . C2 . 120.00(8) yes
C1 . N1 . C3 . 122.41(8) yes
C2 . N1 . C3 . 117.13(8) yes
C5 . N2 . C8 . 107.30(7) yes
C5 . N2 . C9 . 108.20(7) yes
C8 . N2 . C9 . 114.05(7) yes
C5 . N2 . H1 . 109.1(7) no
C8 . N2 . H1 . 109.0(7) no
C9 . N2 . H1 . 109.1(7) no
N1 . C1 . O1 . 118.47(8) yes
N1 . C1 . O2 . 118.62(8) yes
O1 . C1 . O2 . 122.92(8) yes
N1 . C2 . H21 . 112.0 no
N1 . C2 . H22 . 110.8 no
H21 . C2 . H22 . 107.3 no
N1 . C2 . H23 . 109.3 no
H21 . C2 . H23 . 110.4 no
H22 . C2 . H23 . 106.9 no
N1 . C3 . C4 . 115.38(8) yes
N1 . C3 . H31 . 107.4 no
C4 . C3 . H31 . 110.9 no
N1 . C3 . H32 . 108.1 no
C4 . C3 . H32 . 107.1 no
H31 . C3 . H32 . 107.6 no
C3 . C4 . C5 . 115.58(7) yes
C3 . C4 . H41 . 109.8 no
C5 . C4 . H41 . 108.8 no
C3 . C4 . H42 . 106.9 no
C5 . C4 . H42 . 107.4 no
H41 . C4 . H42 . 108.0 no
C4 . C5 . N2 . 107.04(7) yes
C4 . C5 . C6 . 114.13(8) yes
N2 . C5 . C6 . 103.61(7) yes
C4 . C5 . C11 . 113.98(7) yes
N2 . C5 . C11 . 102.74(7) yes
C6 . C5 . C11 . 113.81(7) yes
C5 . C6 . C7 . 104.62(8) yes
C5 . C6 . H61 . 109.4 no
C7 . C6 . H61 . 109.2 no
C5 . C6 . H62 . 110.5 no
C7 . C6 . H62 . 112.7 no
H61 . C6 . H62 . 110.2 no
C6 . C7 . C8 . 101.87(8) yes
C6 . C7 . H71 . 112.4 no
C8 . C7 . H71 . 111.4 no
C6 . C7 . H72 . 112.1 no
C8 . C7 . H72 . 109.9 no
H71 . C7 . H72 . 109.1 no
C7 . C8 . N2 . 103.67(7) yes
C7 . C8 . H81 . 110.3 no
N2 . C8 . H81 . 108.2 no
C7 . C8 . H82 . 114.9 no
N2 . C8 . H82 . 109.4 no
H81 . C8 . H82 . 110.0 no
N2 . C9 . C10 . 104.02(7) yes
N2 . C9 . H91 . 108.2 no
C10 . C9 . H91 . 114.2 no
N2 . C9 . H92 . 107.7 no
C10 . C9 . H92 . 111.0 no
H91 . C9 . H92 . 111.2 no
C9 . C10 . C11 . 102.36(8) yes
C9 . C10 . H101 . 109.0 no
C11 . C10 . H101 . 110.7 no
C9 . C10 . H102 . 112.0 no
C11 . C10 . H102 . 111.9 no
H101 . C10 . H102 . 110.6 no
C5 . C11 . C10 . 104.96(7) yes
C5 . C11 . H111 . 109.8 no
C10 . C11 . H111 . 110.4 no
C5 . C11 . H112 . 111.3 no
C10 . C11 . H112 . 112.7 no
H111 . C11 . H112 . 107.6 no
H2 . O3 . H3 . 105.4(14) no
H4 . O4 . H5 . 107.2(16) no
H6 . O5 . H7 . 107.7(15) no
H8 . O6 . H9 . 106.7(15) 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 . H1 . O1 1_655 163.5(10) 0.904 1.810 2.6889(14) yes
N2 . H1 . O2 1_655 132.9(9) 0.904 2.532 3.2170(14) yes
N2 . H1 . C1 1_655 159.2(9) 0.904 2.471 3.3319(14) yes
C11 . H112 . N1 . 130.12(3) 0.971 2.544 3.2552(14) yes
O3 . H2 . O1 . 173.9(14) 0.842 1.917 2.7556(14) yes
O3 . H3 . O6 4_555 173.6(14) 0.832 1.900 2.7284(14) yes
O4 . H4 . O3 . 173.3(16) 0.821 1.996 2.8130(14) yes
O4 . H5 . O3 2_566 170.8(17) 0.805 2.028 2.8249(14) yes
O5 . H6 . O2 . 176.5(15) 0.820 1.952 2.7701(14) yes
O5 . H7 . O2 2_556 167.7(14) 0.833 1.973 2.7922(14) yes
O6 . H8 . O5 . 177.0(15) 0.808 1.925 2.7325(14) yes
O6 . H9 . O4 4_554 173.0(15) 0.818 1.955 2.7690(14) yes


