# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_publ_contact_author_name 'Stephen Moggach'
_publ_contact_author_email SMOGGACH@STAFFMAIL.ED.AC.UK
_publ_section_title
;
The Effect of Pressure on the Porous Peptide L-Alanyl-L-Valine
;
_publ_contact_author_address
;
Dr Stephen Moggach
RSE Personal Research Fellow
The University of Edinburgh
Joseph Black Building
West Mains Road
Edinburgh
EH9 3JJ
;
_publ_contact_author_phone '+44(0)131 6504806'
loop_
_publ_author_name
'Stephen Moggach'
'Carl Henrik Gorbitz'
'John E. Warren'
# Attachment 'porous_peptides.cif'
data_ambient
_database_code_depnum_ccdc_archive 'CCDC 761398'
#TrackingRef 'porous_peptides.cif'
_audit_creation_date 10-01-13
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title 'VALAL1 in P6(1)'
_chemical_name_systematic L-alanyl-L-valine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 326.00 A**3
220_ALERT_2_B Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.41 Ratio
222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.31 Ratio
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5
234_ALERT_4_C Large Hirshfeld Difference C5 -- C6 .. 0.17 Ang.
340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
All of the above are caused by large thermal parameters on the methyl
groups on the L-Valine side chain and are reffered to in the text.
242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
This is caused by a 'rocking' motion on the oxygen atoms attached
to the carboxyl group C-atom C8. They are not particularly
large though and dont warrent modelling as disordered.
919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 2
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
No action taken.
960_ALERT_3_G Number of Intensities with I .LT. - 2*sig(I) .. 1
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 2
#==============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#==============================================================================
Theta sin(th)/Lambda Complete Expected Measured Missing
#------------------------------------------------------------------------------
20.82 0.500 0.999 677 676 1
23.01 0.550 0.998 889 887 2
25.24 0.600 0.999 1154 1153 1
#----------------------------------------------------------- ACTA Min. Res. ---
27.51 0.650 0.999 1458 1457 1
29.84 0.700 0.999 1819 1817 2
30.55 0.715 0.999 1947 1945 2
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C4 (Verify) .... S
These are correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
A shelx weighting scheme was not used.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 14.4270(17)
_cell_length_b 14.4270(17)
_cell_length_c 10.0102(15)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 1804.4(4)
_symmetry_cell_setting Hexagonal
_symmetry_space_group_name_H-M 'P 61 '
_symmetry_space_group_name_Hall 'P 61 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x-y,x,z+1/6
-y,x-y,z+1/3
-x,-y,z+1/2
-x+y,-x,z+2/3
y,-x+y,z+5/6
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 6
# Given Formula = C8 H16 N2 O3
# Dc = 1.04 Fooo = 612.00 Mu = 0.79 M = 188.23
# Found Formula = C8 H16 N2 O3
# Dc = 1.04 FOOO = 612.00 Mu = 0.79 M = 188.23
_chemical_formula_sum 'C8 H16 N2 O3'
_chemical_formula_moiety 'C8 H16 N2 O3'
_chemical_compound_source ?
_chemical_formula_weight 188.23
_cell_measurement_reflns_used 4576
_cell_measurement_theta_min 3
_cell_measurement_theta_max 20
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_max 0.200
_exptl_crystal_density_diffrn 1.039
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 612
_exptl_absorpt_coefficient_mu 0.079
# Sheldrick geometric approximatio 0.98 0.99
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.89
_exptl_absorpt_correction_T_max 0.99
_diffrn_measurement_device-type 'Bruker Kappa Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method '\f & \w 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 'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 293
_diffrn_reflns_number 55579
_reflns_number_total 1945
_diffrn_reflns_av_R_equivalents 0.110
# Number of reflections without Friedels Law is 1945
# Number of reflections with Friedels Law is 0
# Theoretical number of reflections is about 1843
_diffrn_reflns_theta_min 1.630
_diffrn_reflns_theta_max 30.548
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full 30.548
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 20
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_k_max 20
_diffrn_reflns_limit_l_min -10
_diffrn_reflns_limit_l_max 14
_reflns_limit_h_min -17
_reflns_limit_h_max 0
_reflns_limit_k_min 0
_reflns_limit_k_max 20
_reflns_limit_l_min 0
_reflns_limit_l_max 14
_oxford_diffrn_Wilson_B_factor 3.47
_oxford_diffrn_Wilson_scale 0.19
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.48
_refine_diff_density_max 0.60
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 1944
_refine_ls_number_restraints 1
_refine_ls_number_parameters 118
_oxford_refine_ls_R_factor_ref 0.1111
_refine_ls_wR_factor_ref 0.2188
_refine_ls_goodness_of_fit_ref 0.9999
_refine_ls_shift/su_max 0.0060463
_refine_ls_shift/su_mean 0.1846178
# The values computed from all data
_oxford_reflns_number_all 1944
_refine_ls_R_factor_all 0.1111
_refine_ls_wR_factor_all 0.2188
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 1020
_refine_ls_R_factor_gt 0.0648
_refine_ls_wR_factor_gt 0.1665
# 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 unk
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, 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/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
6.38 8.62 2.61
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C.,
Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.4873(3) 0.2200(3) 0.9984(4) 0.0378 1.0000 Uani . . . . . . .
C2 C 0.3748(4) 0.1796(5) 0.9463(7) 0.0741 1.0000 Uani . . . . . . .
C3 C 0.5623(3) 0.2227(3) 0.8898(4) 0.0365 1.0000 Uani . . . . . . .
C4 C 0.6265(3) 0.1247(3) 0.7579(4) 0.0437 1.0000 Uani . . . . . . .
C5 C 0.7228(5) 0.1212(6) 0.8190(7) 0.0805 1.0000 Uani . . . . . . .
C6 C 0.7833(11) 0.0943(15) 0.7190(13) 0.1607 1.0000 Uani . . . . . . .
C7 C 0.7977(7) 0.2232(9) 0.8929(9) 0.1111 1.0000 Uani . . . . . . .
C8 C 0.5599(4) 0.0263(3) 0.6679(5) 0.0496 1.0000 Uani . . . . . . .
N1 N 0.5330(3) 0.3313(3) 1.0475(4) 0.0407 1.0000 Uani . . . . . . .
N2 N 0.5593(3) 0.1312(2) 0.8625(4) 0.0428 1.0000 Uani . . . . . . .
O1 O 0.6208(2) 0.3082(2) 0.8331(4) 0.0490 1.0000 Uani . . . . . . .
O2 O 0.4879(4) -0.0550(3) 0.7208(5) 0.1064 1.0000 Uani . . . . . . .
O3 O 0.5864(3) 0.0335(2) 0.5496(4) 0.0557 1.0000 Uani . . . . . . .
H11 H 0.4852 0.1740 1.0717 0.0454 1.0000 Uiso R . . . . . .
H12 H 0.4914 0.3334 1.1116 0.0490 1.0000 Uiso R . . . . . .
H13 H 0.5983 0.3537 1.0801 0.0490 1.0000 Uiso R . . . . . .
H14 H 0.5370 0.3735 0.9804 0.0490 1.0000 Uiso R . . . . . .
H21 H 0.3459 0.1075 0.9148 0.0895 1.0000 Uiso R . . . . . .
H22 H 0.3306 0.1812 1.0170 0.0895 1.0000 Uiso R . . . . . .
H23 H 0.3768 0.2245 0.8743 0.0895 1.0000 Uiso R . . . . . .
H24 H 0.5169 0.0747 0.9072 0.0513 1.0000 Uiso R . . . . . .
H41 H 0.6538 0.1891 0.7023 0.0525 1.0000 Uiso R . . . . . .
H51 H 0.6937 0.0636 0.8854 0.0969 1.0000 Uiso R . . . . . .
H61 H 0.8422 0.0936 0.7627 0.1955 1.0000 Uiso R . . . . . .
H62 H 0.8100 0.1467 0.6489 0.1955 1.0000 Uiso R . . . . . .
H63 H 0.7363 0.0249 0.6816 0.1955 1.0000 Uiso R . . . . . .
H71 H 0.8563 0.2174 0.9289 0.1342 1.0000 Uiso R . . . . . .
H72 H 0.7596 0.2339 0.9643 0.1342 1.0000 Uiso R . . . . . .
H73 H 0.8248 0.2829 0.8325 0.1342 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0403(16) 0.0334(16) 0.0356(16) 0.0042(14) 0.0029(14) 0.0153(14)
C2 0.044(2) 0.094(4) 0.074(4) -0.014(3) -0.002(2) 0.027(3)
C3 0.0451(18) 0.0368(16) 0.0271(13) 0.0003(13) 0.0013(13) 0.0202(14)
C4 0.052(2) 0.0401(18) 0.0299(16) -0.0048(13) 0.0042(15) 0.0165(16)
C5 0.078(4) 0.108(5) 0.068(3) -0.029(4) -0.017(3) 0.056(4)
C6 0.161(10) 0.264(15) 0.111(8) -0.054(10) -0.022(8) 0.147(11)
C7 0.100(5) 0.157(8) 0.103(6) -0.057(6) -0.043(5) 0.085(6)
C8 0.066(2) 0.0372(18) 0.038(2) 0.0004(15) 0.0095(18) 0.0202(18)
N1 0.0486(17) 0.0469(16) 0.0356(14) 0.0003(13) 0.0021(13) 0.0306(14)
N2 0.0581(18) 0.0326(13) 0.0317(13) 0.0004(12) 0.0101(13) 0.0183(13)
O1 0.0594(15) 0.0417(14) 0.0467(15) 0.0094(12) 0.0196(14) 0.0258(13)
O2 0.135(4) 0.0419(18) 0.070(3) -0.0137(18) 0.055(3) -0.010(2)
O3 0.082(2) 0.0382(13) 0.0305(13) -0.0024(11) 0.0057(14) 0.0174(14)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.3090(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.515(6) yes
C1 . C3 . 1.522(5) yes
C1 . N1 . 1.481(5) yes
C1 . H11 . 0.980 no
C2 . H21 . 0.960 no
C2 . H22 . 0.960 no
C2 . H23 . 0.960 no
C3 . N2 . 1.327(5) yes
C3 . O1 . 1.230(5) yes
C4 . C5 . 1.542(8) yes
C4 . C8 . 1.544(5) yes
C4 . N2 . 1.462(5) yes
C4 . H41 . 0.980 no
C5 . C6 . 1.502(13) yes
C5 . C7 . 1.513(10) yes
C5 . H51 . 0.980 no
C6 . H61 . 0.960 no
C6 . H62 . 0.960 no
C6 . H63 . 0.960 no
C7 . H71 . 0.960 no
C7 . H72 . 0.960 no
C7 . H73 . 0.960 no
C8 . O2 . 1.232(5) yes
C8 . O3 . 1.233(5) yes
N1 . H12 . 0.890 no
N1 . H13 . 0.890 no
N1 . H14 . 0.890 no
N2 . H24 . 0.860 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C3 . 112.0(3) yes
C2 . C1 . N1 . 110.0(4) yes
C3 . C1 . N1 . 106.5(3) yes
C2 . C1 . H11 . 109.5 no
C3 . C1 . H11 . 109.4 no
N1 . C1 . H11 . 109.4 no
C1 . C2 . H21 . 109.4 no
C1 . C2 . H22 . 109.5 no
H21 . C2 . H22 . 109.5 no
C1 . C2 . H23 . 109.5 no
H21 . C2 . H23 . 109.5 no
H22 . C2 . H23 . 109.5 no
C1 . C3 . N2 . 116.9(3) yes
C1 . C3 . O1 . 118.5(3) yes
N2 . C3 . O1 . 124.6(3) yes
C5 . C4 . C8 . 111.0(4) yes
C5 . C4 . N2 . 110.8(4) yes
C8 . C4 . N2 . 110.4(3) yes
C5 . C4 . H41 . 108.3 no
C8 . C4 . H41 . 108.1 no
N2 . C4 . H41 . 108.2 no
C4 . C5 . C6 . 113.2(7) yes
C4 . C5 . C7 . 112.3(6) yes
C6 . C5 . C7 . 110.6(8) yes
C4 . C5 . H51 . 106.7 no
C6 . C5 . H51 . 106.9 no
C7 . C5 . H51 . 106.8 no
C5 . C6 . H61 . 109.3 no
C5 . C6 . H62 . 109.8 no
H61 . C6 . H62 . 109.5 no
C5 . C6 . H63 . 109.3 no
H61 . C6 . H63 . 109.5 no
H62 . C6 . H63 . 109.5 no
C5 . C7 . H71 . 109.3 no
C5 . C7 . H72 . 109.4 no
H71 . C7 . H72 . 109.5 no
C5 . C7 . H73 . 109.7 no
H71 . C7 . H73 . 109.5 no
H72 . C7 . H73 . 109.5 no
C4 . C8 . O2 . 117.8(4) yes
C4 . C8 . O3 . 117.3(4) yes
O2 . C8 . O3 . 124.8(4) yes
C1 . N1 . H12 . 109.5 no
C1 . N1 . H13 . 109.4 no
H12 . N1 . H13 . 109.5 no
C1 . N1 . H14 . 109.5 no
H12 . N1 . H14 . 109.5 no
H13 . N1 . H14 . 109.5 no
C4 . N2 . C3 . 121.2(3) yes
C4 . N2 . H24 . 119.5 no
C3 . N2 . H24 . 119.4 no
_chemical_name_common L-alanyl-L-valine
data_pressure
_database_code_depnum_ccdc_archive 'CCDC 761399'
#TrackingRef 'porous_peptides.cif'
_audit_creation_date 10-01-14
_audit_creation_method CRYSTALS_ver_14.01
_oxford_structure_analysis_title 'alva21 in P61'
_chemical_name_systematic L-alanyl-L-valine
_chemical_melting_point ?
_publ_section_exptl_refinement
;
601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of . 265.00 A**3
This is known, and reffered to in the text.
022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.84
027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 13.12 Deg.
029_ALERT_3_B _diffrn_measured_fraction_theta_full Low ....... 0.96
919_ALERT_3_B Reflection(s) # Likely Affected by the Beamstop 1
026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc.
089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.83
234_ALERT_4_C Large Hirshfeld Difference C5 -- C7 .. 0.16 Ang.
340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10
951_ALERT_1_C Reported and Calculated Kmax Values Differ by .. 3
910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1
913_ALERT_3_C Missing # of Very Strong Reflections in FCF .... 2
911_ALERT_3_B Missing # FCF Refl Between THmin & STh/L= 0.600 227
912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 19
These are all caused by shading of the pressure cell.
432_ALERT_2_C Short Inter X...Y Contact O1 .. C1 .. 3.00 Ang.
This is expected at pressure.
860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 29
All 1,2 and 1,3 distances were restraied to ambient pressure values.
See text.
092_ALERT_4_G Check: Wavelength given is not Cu,Mo or Ag Ka .. 0.49 Ang.
199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
791_ALERT_4_G The Model has Chirality at C1 (Verify) .... S
791_ALERT_4_G The Model has Chirality at C4 (Verify) .... S
These are correct.
929_ALERT_4_G No Interpretable (SHELX) Weight Parameters found ?
Shelx weights were not used.
760_ALERT_1_G CIF Contains no Torsion Angles ................. ?
No action taken.
;
_publ_section_exptl_prep
# Brief details or a reference. Include solvent if known
;
?
;
#end of refcif
_cell_length_a 13.9836(19)
_cell_length_b 13.9836(19)
_cell_length_c 9.9229(15)
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 120
_cell_volume 1680.4(4)
_symmetry_cell_setting Hexagonal
_symmetry_space_group_name_H-M 'P 61 '
_symmetry_space_group_name_Hall 'P 61 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x-y,x,z+1/6
-y,x-y,z+1/3
-x,-y,z+1/2
-x+y,-x,z+2/3
y,-x+y,z+5/6
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 0.0006 0.0007 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'
N 0.0016 0.0014 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 0.0037 0.0026 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'
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'
_cell_formula_units_Z 6
# Given Formula = C8 H16 N2 O3
# Dc = 1.12 Fooo = 612.00 Mu = 0.16 M = 188.23
# Found Formula = C8 H16 N2 O3
# Dc = 1.12 FOOO = 612.00 Mu = 0.16 M = 188.23
_chemical_formula_sum 'C8 H16 N2 O3'
_chemical_formula_moiety 'C8 H16 N2 O3'
_chemical_compound_source ?
_chemical_formula_weight 188.23
_cell_measurement_reflns_used 3576
_cell_measurement_theta_min 2
_cell_measurement_theta_max 18
_cell_measurement_temperature 293
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_min 0.100
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_max 0.200
_exptl_crystal_density_diffrn 1.116
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 612
_exptl_absorpt_coefficient_mu 0.016
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min 0.99
_exptl_absorpt_correction_T_max 1.00
_diffrn_measurement_device_type 'Bruker Apex2'
_diffrn_measurement_device Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type ' synchrotron'
_diffrn_radiation_wavelength 0.48720
_diffrn_measurement_method \w
_computing_data_collection 'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement 'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction 'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution 'USER DEFINED STRUCTURE SOLUTION'
_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 293
_diffrn_reflns_number 13027
_reflns_number_total 987
_diffrn_reflns_av_R_equivalents 0.000
# Number of reflections without Friedels Law is 1111
# Number of reflections with Friedels Law is 987
# Theoretical number of reflections is about 1101
_diffrn_reflns_theta_min 1.819
_diffrn_reflns_theta_max 17.490
_diffrn_measured_fraction_theta_max 0.843
_diffrn_reflns_theta_full 13.117
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_limit_h_min -17
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_reflns_limit_h_min -13
_reflns_limit_h_max 0
_reflns_limit_k_min 0
_reflns_limit_k_max 17
_reflns_limit_l_min 0
_reflns_limit_l_max 12
_oxford_diffrn_Wilson_B_factor 2.93
_oxford_diffrn_Wilson_scale 4.98
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.42
_refine_diff_density_max 0.42
# 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 924
_refine_ls_number_restraints 29
_refine_ls_number_parameters 118
_oxford_refine_ls_R_factor_ref 0.1276
_refine_ls_wR_factor_ref 0.1712
_refine_ls_goodness_of_fit_ref 1.0131
_refine_ls_shift/su_max 0.0000609
_refine_ls_shift/su_mean 0.0000529
# The values computed from all data
_oxford_reflns_number_all 924
_refine_ls_R_factor_all 0.1276
_refine_ls_wR_factor_all 0.1712
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 469
_refine_ls_R_factor_gt 0.0615
_refine_ls_wR_factor_gt 0.1376
# 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 unk
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method= Modified Sheldrick
w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.47P]
,where P=(max(Fo^2^,0) + 2Fc^2^)/3
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
User-defined structure solution reference
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Bruker Analytical X-ray Systems, Inc., 2006. Apex2,
Version 2 User Manual, M86-E01078, Madison, WI.
Siemens Industrial Automation, Inc (1996).
SADABS: Area-Detector Absorption Correction;: Madison, WI.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached 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
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.4826(4) 0.2181(4) 0.9884(5) 0.0361 1.0000 Uani D . . . . . .
C2 C 0.3701(6) 0.1810(7) 0.9276(8) 0.0748 1.0000 Uani D . . . . . .
C3 C 0.5639(5) 0.2245(5) 0.8822(5) 0.0365 1.0000 Uani D . . . . . .
C4 C 0.6428(5) 0.1289(5) 0.7584(5) 0.0419 1.0000 Uani D . . . . . .
C5 C 0.7451(5) 0.1323(6) 0.8197(6) 0.0543 1.0000 Uani D . . . . . .
C6 C 0.8099(7) 0.1104(8) 0.7127(8) 0.0821 1.0000 Uani D . . . . . .
C7 C 0.8207(6) 0.2420(6) 0.8878(7) 0.0689 1.0000 Uani D . . . . . .
C8 C 0.5754(5) 0.0249(4) 0.6766(5) 0.0416 1.0000 Uani D . . . . . .
N1 N 0.5299(4) 0.3301(4) 1.0443(5) 0.0423 1.0000 Uani D . . . . . .
N2 N 0.5727(4) 0.1369(4) 0.8635(5) 0.0395 1.0000 Uani D . . . . . .
O1 O 0.6153(4) 0.3098(4) 0.8180(5) 0.0533 1.0000 Uani D . . . . . .
O2 O 0.5188(5) -0.0622(4) 0.7404(5) 0.0723 1.0000 Uani D . . . . . .
O3 O 0.5871(4) 0.0316(4) 0.5500(4) 0.0561 1.0000 Uani D . . . . . .
H11 H 0.4761 0.1667 1.0597 0.0434 1.0000 Uiso R . . . . . .
H12 H 0.4850 0.3308 1.1075 0.0508 1.0000 Uiso R . . . . . .
H13 H 0.5955 0.3504 1.0805 0.0508 1.0000 Uiso R . . . . . .
H14 H 0.5377 0.3770 0.9789 0.0508 1.0000 Uiso R . . . . . .
H21 H 0.3406 0.1079 0.8917 0.0898 1.0000 Uiso R . . . . . .
H22 H 0.3215 0.1809 0.9960 0.0898 1.0000 Uiso R . . . . . .
H23 H 0.3770 0.2308 0.8567 0.0898 1.0000 Uiso R . . . . . .
H24 H 0.5357 0.0809 0.9153 0.0475 1.0000 Uiso R . . . . . .
H41 H 0.6677 0.1924 0.6980 0.0503 1.0000 Uiso R . . . . . .
H51 H 0.7204 0.0739 0.8878 0.0652 1.0000 Uiso R . . . . . .
H61 H 0.8735 0.1130 0.7532 0.0984 1.0000 Uiso R . . . . . .
H62 H 0.8332 0.1656 0.6435 0.0984 1.0000 Uiso R . . . . . .
H63 H 0.7638 0.0388 0.6738 0.0984 1.0000 Uiso R . . . . . .
H71 H 0.8836 0.2408 0.9248 0.0826 1.0000 Uiso R . . . . . .
H72 H 0.7813 0.2540 0.9589 0.0826 1.0000 Uiso R . . . . . .
H73 H 0.8450 0.3005 0.8230 0.0826 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.046(4) 0.041(5) 0.022(3) -0.001(3) 0.002(3) 0.022(4)
C2 0.066(7) 0.098(8) 0.062(5) -0.008(5) 0.000(5) 0.043(6)
C3 0.046(5) 0.033(4) 0.032(3) -0.001(3) 0.008(3) 0.021(4)
C4 0.048(5) 0.044(5) 0.029(3) -0.005(3) 0.005(3) 0.020(4)
C5 0.055(5) 0.054(5) 0.043(4) -0.003(4) 0.003(4) 0.019(4)
C6 0.075(7) 0.103(8) 0.080(6) -0.032(6) -0.004(6) 0.053(6)
C7 0.063(6) 0.084(7) 0.059(5) -0.002(5) -0.008(5) 0.036(5)
C8 0.043(5) 0.042(5) 0.039(4) -0.005(4) 0.006(4) 0.020(4)
N1 0.059(4) 0.049(4) 0.028(3) -0.001(3) 0.006(3) 0.033(4)
N2 0.047(4) 0.037(4) 0.027(3) 0.004(3) 0.012(3) 0.015(3)
O1 0.071(4) 0.045(3) 0.045(3) 0.013(3) 0.024(3) 0.031(3)
O2 0.093(5) 0.048(4) 0.046(3) -0.002(3) 0.027(3) 0.013(4)
O3 0.082(4) 0.044(3) 0.026(2) -0.003(2) 0.001(2) 0.020(3)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.500(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
C1 . C2 . 1.514(7) yes
C1 . C3 . 1.520(6) yes
C1 . N1 . 1.471(6) yes
C1 . H11 . 0.980 no
C2 . H21 . 0.960 no
C2 . H22 . 0.960 no
C2 . H23 . 0.960 no
C3 . N2 . 1.304(6) yes
C3 . O1 . 1.220(6) yes
C4 . C5 . 1.533(7) yes
C4 . C8 . 1.514(6) yes
C4 . N2 . 1.474(6) yes
C4 . H41 . 0.980 no
C5 . C6 . 1.523(7) yes
C5 . C7 . 1.519(7) yes
C5 . H51 . 0.980 no
C6 . H61 . 0.960 no
C6 . H62 . 0.960 no
C6 . H63 . 0.960 no
C7 . H71 . 0.960 no
C7 . H72 . 0.960 no
C7 . H73 . 0.960 no
C8 . O2 . 1.244(6) yes
C8 . O3 . 1.263(6) yes
N1 . H12 . 0.890 no
N1 . H13 . 0.890 no
N1 . H14 . 0.890 no
N2 . H24 . 0.860 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C3 . 111.3(5) yes
C2 . C1 . N1 . 110.6(5) yes
C3 . C1 . N1 . 106.0(4) yes
C2 . C1 . H11 . 109.6 no
C3 . C1 . H11 . 109.6 no
N1 . C1 . H11 . 109.6 no
C1 . C2 . H21 . 109.5 no
C1 . C2 . H22 . 109.5 no
H21 . C2 . H22 . 109.5 no
C1 . C2 . H23 . 109.5 no
H21 . C2 . H23 . 109.5 no
H22 . C2 . H23 . 109.5 no
C1 . C3 . N2 . 117.6(4) yes
C1 . C3 . O1 . 118.5(4) yes
N2 . C3 . O1 . 124.0(5) yes
C5 . C4 . C8 . 111.5(4) yes
C5 . C4 . N2 . 111.3(4) yes
C8 . C4 . N2 . 109.5(4) yes
C5 . C4 . H41 . 108.2 no
C8 . C4 . H41 . 108.1 no
N2 . C4 . H41 . 108.2 no
C4 . C5 . C6 . 110.9(5) yes
C4 . C5 . C7 . 112.1(5) yes
C6 . C5 . C7 . 109.3(5) yes
C4 . C5 . H51 . 108.2 no
C6 . C5 . H51 . 108.2 no
C7 . C5 . H51 . 108.2 no
C5 . C6 . H61 . 109.5 no
C5 . C6 . H62 . 109.5 no
H61 . C6 . H62 . 109.5 no
C5 . C6 . H63 . 109.5 no
H61 . C6 . H63 . 109.5 no
H62 . C6 . H63 . 109.5 no
C5 . C7 . H71 . 109.5 no
C5 . C7 . H72 . 109.5 no
H71 . C7 . H72 . 109.5 no
C5 . C7 . H73 . 109.5 no
H71 . C7 . H73 . 109.5 no
H72 . C7 . H73 . 109.5 no
C4 . C8 . O2 . 117.0(4) yes
C4 . C8 . O3 . 117.8(5) yes
O2 . C8 . O3 . 125.0(5) yes
C1 . N1 . H12 . 109.5 no
C1 . N1 . H13 . 109.5 no
H12 . N1 . H13 . 109.5 no
C1 . N1 . H14 . 109.5 no
H12 . N1 . H14 . 109.5 no
H13 . N1 . H14 . 109.5 no
C4 . N2 . C3 . 123.4(4) yes
C4 . N2 . H24 . 118.3 no
C3 . N2 . H24 . 118.3 no
_chemical_name_common L-alanyl-L-valine