# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full CrystEngComm
#===============================================================================
# 2. PROCESSING SUMMARY (JOURNAL OFFICE ONLY)
_journal_coden_Cambridge 1350
#TrackingRef 'L-AAfinalNEW.cif'
#==============================================================================
# 0. AUDIT DETAILS
_audit_creation_date 'Aug 24 23:59:22 2010'
_audit_creation_method 'PLATON
option'
_audit_update_record
;
;
#===============================================================================
# 1. SUBMISSION DETAILS
_publ_contact_author_name 'Prof.T.N.Guru Row'
_publ_contact_author_address
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore, 560 012
India
;
_publ_contact_author_email ssctng@sscu.iisc.ernet.in
_publ_contact_author_fax '(91) 80 2360 1310'
_publ_contact_author_phone '(91) 80 2293 2796'
_publ_requested_coeditor_name ?
_publ_contact_letter
;
Please consider this CIF submission for publication in
CrystEngComm as a new-style paper.
All required files have been provided.
The manuscript has passed the checkcif tests and generates an acceptable
printcif output.
Yours sincerely
T. N. Guru Row.
;
_journal_year ?
_journal_volume ?
_journal_issue ?
_journal_page_first ?
_journal_page_last ?
#===============================================================================
# 3. TITLE AND AUTHOR LIST
_publ_section_title
;
;
_publ_section_title_footnote
;
;
# The loop structure below should contain the names and adresses of all
# authors, in the required order of publication. Repeat as necessary.
loop_
_publ_author_name
_publ_author_address
'Archi Dasgupta '
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012, Karnataka
India
;
'T.N.Guru Row'
;
Solid State and Structural Chemistry Unit
Indian Institute of Science
Bangalore 560 012, Karnataka
India
;
#===============================================================================
# 4. TEXT
_publ_section_synopsis
;
?
;
_publ_section_abstract
;
?
;
# Insert blank lines between paragraphs
_publ_section_comment
;
;
_publ_section_exptl_prep
;
?
;
_publ_section_exptl_refinement
;
;
_publ_section_references
;
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837--838.
Sheldrick, G.M. (1997). SHELXL97. University of G\"ottingen, Germany.
Spek, A.L. (2003). J. Appl. Cryst. 36, 7--13.
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical
Crystallography Laboratory, University of Oxford, England.
;
_publ_section_acknowledgements
;
We thank the Department of Science and Technology, India, for use of the CCD
facility setup under the IRHPA-DST program at IISc.
;
_publ_section_figure_captions
;
Fig. 1.
View of the molecular structure of (I) showing the atom
labelling scheme. Displacement ellipsoids are showed at the 50%
probability level. H atoms are shown as small spheres of
arbitrary radii.
;
#===END
# Attachment 'acetamidofinalNEW.cif'
# CIF-file generated for acetamido in P -1
#==============================================================================
#===============================================================================
data_acetamido
_database_code_depnum_ccdc_archive 'CCDC 791931'
#TrackingRef 'acetamidofinalNEW.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C9 H7 Cl2 N5, C2 H5 N O'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C11 H12 Cl2 N6 O'
_chemical_formula_iupac ?
_chemical_formula_weight 315.17
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_Hall '-P 1'
_symmetry_space_group_name_H-M 'P -1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z
_cell_length_a 7.7752(3)
_cell_length_b 9.6284(4)
_cell_length_c 10.4511(3)
_cell_angle_alpha 106.390(3)
_cell_angle_beta 107.730(3)
_cell_angle_gamma 101.093(3)
_cell_volume 680.98(5)
_cell_formula_units_Z 2
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 14019
_cell_measurement_theta_min 2.5
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.537
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 324
_exptl_absorpt_coefficient_mu 0.482
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.8690
_exptl_absorpt_correction_T_max 0.9098
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 14019
_diffrn_reflns_av_R_equivalents 0.0187
_diffrn_reflns_av_sigmaI/netI 0.0107
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.55
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 2400
# number of observed reflections (> n sig(I))
_reflns_number_gt 2163
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.9261P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 2400
_refine_ls_number_parameters 190
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0587
_refine_ls_R_factor_gt 0.0546
_refine_ls_wR_factor_ref 0.1628
_refine_ls_wR_factor_gt 0.1590
_refine_ls_goodness_of_fit_ref 0.894
_refine_ls_restrained_S_all 1.894
_refine_ls_shift/su_max 0.030
_refine_ls_shift/su_mean 0.001
_refine_diff_density_max 1.332
_refine_diff_density_min -0.392
_refine_diff_density_rms 0.069
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6271(4) 0.3708(3) 0.1223(3) 0.0345(6) Uani 1 1 d . . .
C2 C 0.6221(4) 0.4966(4) 0.2272(3) 0.0395(7) Uani 1 1 d . . .
C3 C 0.7134(4) 0.6405(4) 0.2428(3) 0.0426(8) Uani 1 1 d . . .
H3 H 0.7144 0.7239 0.3148 0.051 Uiso 1 1 calc R . .
C4 C 0.8036(4) 0.6622(4) 0.1525(4) 0.0440(8) Uani 1 1 d . . .
H4 H 0.8619 0.7609 0.1632 0.053 Uiso 1 1 calc R . .
C5 C 0.8106(4) 0.5403(3) 0.0448(4) 0.0374(7) Uani 1 1 d . . .
H5 H 0.8700 0.5564 -0.0169 0.045 Uiso 1 1 calc R . .
C6 C 0.7232(4) 0.3907(3) 0.0337(3) 0.0305(6) Uani 1 1 d . . .
C7 C 0.7288(4) 0.2587(3) -0.0800(3) 0.0287(6) Uani 1 1 d . . .
C8 C 0.8314(4) 0.1550(3) -0.0498(3) 0.0263(6) Uani 1 1 d . . .
C9 C 0.7142(4) 0.0236(3) -0.2911(3) 0.0270(6) Uani 1 1 d . . .
C10 C 0.0955(5) 0.7374(4) 0.5719(3) 0.0431(7) Uani 1 1 d . . .
C11 C 0.1655(6) 0.9079(4) 0.6257(5) 0.0591(10) Uani 1 1 d . . .
H11A H 0.0594 0.9466 0.6050 0.089 Uiso 1 1 calc R . .
H11B H 0.2459 0.9390 0.5785 0.089 Uiso 1 1 calc R . .
H11C H 0.2360 0.9471 0.7280 0.089 Uiso 1 1 calc R . .
Cl1 Cl 0.50274(14) 0.18947(10) 0.09659(10) 0.0533(3) Uani 1 1 d . . .
Cl2 Cl 0.49505(16) 0.47231(12) 0.33299(11) 0.0623(3) Uani 1 1 d . . .
H6A H 0.228(7) 0.711(5) 0.444(5) 0.065(13) Uiso 1 1 d . . .
H6B H 0.130(7) 0.580(6) 0.449(5) 0.061(15) Uiso 1 1 d . . .
N1 N 0.9438(4) 0.1773(3) 0.0841(2) 0.0376(6) Uani 1 1 d . . .
H1A H 1.0075 0.1157 0.0989 0.045 Uiso 1 1 calc R . .
H1B H 0.9526 0.2534 0.1555 0.045 Uiso 1 1 calc R . .
N2 N 0.8212(3) 0.0361(2) -0.1578(2) 0.0270(5) Uani 1 1 d . . .
N3 N 0.6846(4) -0.1020(3) -0.4028(2) 0.0392(6) Uani 1 1 d . . .
H3A H 0.6186 -0.1119 -0.4892 0.047 Uiso 1 1 calc R . .
H3B H 0.7318 -0.1724 -0.3877 0.047 Uiso 1 1 calc R . .
N4 N 0.6354(4) 0.1274(3) -0.3247(2) 0.0358(6) Uani 1 1 d . . .
N5 N 0.6445(4) 0.2461(3) -0.2138(3) 0.0353(6) Uani 1 1 d . . .
N6 N 0.1535(5) 0.6614(5) 0.4760(4) 0.0529(8) Uani 1 1 d . . .
O1 O -0.0139(4) 0.6738(3) 0.6172(3) 0.0645(8) Uani 1 1 d . . .
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 0.0384(15) 0.0356(15) 0.0359(15) 0.0168(12) 0.0155(13) 0.0171(12)
C2 0.0431(16) 0.0486(18) 0.0329(15) 0.0147(13) 0.0144(13) 0.0275(14)
C3 0.0389(16) 0.0485(19) 0.0377(16) 0.0082(14) 0.0109(13) 0.0244(14)
C4 0.0368(16) 0.0308(16) 0.058(2) 0.0084(14) 0.0165(15) 0.0114(12)
C5 0.0259(13) 0.0249(14) 0.0513(18) 0.0033(12) 0.0095(12) 0.0100(11)
C6 0.0290(13) 0.0349(15) 0.0302(14) 0.0139(12) 0.0095(11) 0.0155(11)
C7 0.0290(13) 0.0314(14) 0.0265(13) 0.0096(11) 0.0103(11) 0.0130(11)
C8 0.0289(13) 0.0260(13) 0.0238(12) 0.0093(10) 0.0100(10) 0.0080(10)
C9 0.0276(13) 0.0301(13) 0.0229(12) 0.0090(11) 0.0100(10) 0.0085(11)
C10 0.0440(17) 0.0479(18) 0.0301(15) 0.0141(14) 0.0087(13) 0.0069(14)
C11 0.063(2) 0.052(2) 0.068(2) 0.0297(19) 0.027(2) 0.0163(18)
Cl1 0.0667(6) 0.0413(5) 0.0694(6) 0.0275(4) 0.0417(5) 0.0174(4)
Cl2 0.0902(7) 0.0782(7) 0.0592(6) 0.0385(5) 0.0544(6) 0.0507(6)
N1 0.0519(15) 0.0389(13) 0.0215(11) 0.0071(10) 0.0084(10) 0.0278(12)
N2 0.0334(12) 0.0253(11) 0.0232(11) 0.0088(9) 0.0097(9) 0.0128(9)
N3 0.0524(15) 0.0367(14) 0.0224(12) 0.0050(10) 0.0072(11) 0.0202(12)
N4 0.0430(14) 0.0403(14) 0.0232(11) 0.0090(10) 0.0085(10) 0.0216(11)
N5 0.0404(13) 0.0403(14) 0.0287(12) 0.0125(11) 0.0114(10) 0.0226(11)
N6 0.0572(19) 0.056(2) 0.0486(18) 0.0216(17) 0.0248(15) 0.0131(17)
O1 0.0846(19) 0.0517(15) 0.0410(14) 0.0008(11) 0.0361(14) -0.0100(13)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(4) . ?
C1 C2 1.402(4) . ?
C1 Cl1 1.727(3) . ?
C2 C3 1.369(5) . ?
C2 Cl2 1.724(3) . ?
C3 C4 1.372(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.425(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.494(4) . ?
C7 N5 1.310(4) . ?
C7 C8 1.437(4) . ?
C8 N2 1.331(3) . ?
C8 N1 1.334(3) . ?
C9 N4 1.342(4) . ?
C9 N2 1.345(3) . ?
C9 N3 1.345(4) . ?
C10 O1 1.238(4) . ?
C10 N6 1.316(5) . ?
C10 C11 1.502(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N4 N5 1.350(3) . ?
N6 H6A 0.88(5) . ?
N6 H6B 0.72(5) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.5(3) . . ?
C6 C1 Cl1 119.4(2) . . ?
C2 C1 Cl1 119.9(2) . . ?
C3 C2 C1 119.8(3) . . ?
C3 C2 Cl2 119.5(2) . . ?
C1 C2 Cl2 120.6(3) . . ?
C2 C3 C4 120.3(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 122.1(3) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C4 C5 C6 117.4(3) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 H5 121.3 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 C7 121.6(3) . . ?
C5 C6 C7 118.5(3) . . ?
N5 C7 C8 119.7(2) . . ?
N5 C7 C6 116.3(2) . . ?
C8 C7 C6 123.9(2) . . ?
N2 C8 N1 118.4(2) . . ?
N2 C8 C7 119.8(2) . . ?
N1 C8 C7 121.8(2) . . ?
N4 C9 N2 125.8(2) . . ?
N4 C9 N3 116.0(2) . . ?
N2 C9 N3 118.2(2) . . ?
O1 C10 N6 122.6(4) . . ?
O1 C10 C11 119.8(3) . . ?
N6 C10 C11 117.6(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C8 N2 C9 115.9(2) . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C9 N4 N5 117.0(2) . . ?
C7 N5 N4 120.9(2) . . ?
C10 N6 H6A 120(3) . . ?
C10 N6 H6B 123(4) . . ?
H6A N6 H6B 117(5) . . ?
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
C6 C1 C2 C3 -0.3(4) . . . . ?
Cl1 C1 C2 C3 -176.9(2) . . . . ?
C6 C1 C2 Cl2 177.5(2) . . . . ?
Cl1 C1 C2 Cl2 0.9(4) . . . . ?
C1 C2 C3 C4 2.6(5) . . . . ?
Cl2 C2 C3 C4 -175.3(2) . . . . ?
C2 C3 C4 C5 -1.7(5) . . . . ?
C3 C4 C5 C6 -1.3(5) . . . . ?
C2 C1 C6 C5 -2.7(4) . . . . ?
Cl1 C1 C6 C5 173.9(2) . . . . ?
C2 C1 C6 C7 -179.3(2) . . . . ?
Cl1 C1 C6 C7 -2.6(4) . . . . ?
C4 C5 C6 C1 3.5(4) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C1 C6 C7 N5 114.8(3) . . . . ?
C5 C6 C7 N5 -61.8(3) . . . . ?
C1 C6 C7 C8 -70.0(4) . . . . ?
C5 C6 C7 C8 113.5(3) . . . . ?
N5 C7 C8 N2 -8.0(4) . . . . ?
C6 C7 C8 N2 176.8(2) . . . . ?
N5 C7 C8 N1 169.2(3) . . . . ?
C6 C7 C8 N1 -5.9(4) . . . . ?
N1 C8 N2 C9 -176.4(2) . . . . ?
C7 C8 N2 C9 0.9(4) . . . . ?
N4 C9 N2 C8 7.6(4) . . . . ?
N3 C9 N2 C8 -173.8(2) . . . . ?
N2 C9 N4 N5 -8.6(4) . . . . ?
N3 C9 N4 N5 172.7(3) . . . . ?
C8 C7 N5 N4 7.1(4) . . . . ?
C6 C7 N5 N4 -177.4(2) . . . . ?
C9 N4 N5 C7 0.7(4) . . . . ?
#===END
#===============================================================================
data_ltghba
_database_code_depnum_ccdc_archive 'CCDC 819591'
#TrackingRef 'FINALltghba.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C9 H8 Cl2 N5, C7 H5 O3'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C16 H13 Cl2 N5 O3'
_chemical_formula_iupac ?
_chemical_formula_weight 394.21
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a 15.5808(10)
_cell_length_b 9.6890(6)
_cell_length_c 11.1057(7)
_cell_angle_alpha 90
_cell_angle_beta 91.312(3)
_cell_angle_gamma 90
_cell_volume 1676.10(18)
_cell_formula_units_Z 4
_cell_measurement_temperature 90(2)
_cell_measurement_reflns_used 9221
_cell_measurement_theta_min 2.5
_cell_measurement_theta_max 25.5
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.20
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.562
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 808
_exptl_absorpt_coefficient_mu 0.416
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.8853
_exptl_absorpt_correction_T_max 0.9214
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 90(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 9221
_diffrn_reflns_av_R_equivalents 0.0255
_diffrn_reflns_av_sigmaI/netI 0.0321
_diffrn_reflns_limit_h_min -18
_diffrn_reflns_limit_h_max 18
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_theta_min 2.48
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_full 25.50
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_reduction_process
;
;
_reflns_number_total 3075
# number of observed reflections (> n sig(I))
_reflns_number_gt 2539
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0413P)^2^+1.1953P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3075
_refine_ls_number_parameters 240
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0494
_refine_ls_R_factor_gt 0.0371
_refine_ls_wR_factor_ref 0.0913
_refine_ls_wR_factor_gt 0.0872
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.281
_refine_diff_density_min -0.280
_refine_diff_density_rms 0.055
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.39944(3) 0.48763(6) 0.58325(5) 0.02368(15) Uani 1 1 d . . .
Cl2 Cl 0.20042(4) 0.43949(7) 0.61033(5) 0.03209(17) Uani 1 1 d . . .
N2 N 0.55977(10) 0.86315(18) 0.58257(15) 0.0169(4) Uani 1 1 d . . .
N1 N 0.41485(10) 0.90277(19) 0.57683(16) 0.0191(4) Uani 1 1 d . . .
H1A H 0.4217 0.9633 0.5213 0.023 Uiso 1 1 calc R . .
H1B H 0.3643 0.8856 0.6025 0.023 Uiso 1 1 calc R . .
N4 N 0.61410(11) 0.70443(19) 0.72563(16) 0.0186(4) Uani 1 1 d . . .
N3 N 0.70391(10) 0.81235(19) 0.59487(16) 0.0194(4) Uani 1 1 d . . .
H3A H 0.7130 0.8694 0.5372 0.023 Uiso 1 1 calc R . .
H3B H 0.7461 0.7676 0.6274 0.023 Uiso 1 1 calc R . .
C1 C 0.34044(13) 0.5878(2) 0.68059(19) 0.0182(5) Uani 1 1 d . . .
C7 C 0.47032(12) 0.7322(2) 0.71527(18) 0.0165(4) Uani 1 1 d . . .
C8 C 0.48180(12) 0.8363(2) 0.62259(18) 0.0166(4) Uani 1 1 d . . .
C2 C 0.25268(13) 0.5656(2) 0.69253(19) 0.0207(5) Uani 1 1 d . . .
C6 C 0.38118(13) 0.6934(2) 0.74550(19) 0.0178(5) Uani 1 1 d . . .
N5 N 0.53539(10) 0.67037(19) 0.76558(16) 0.0194(4) Uani 1 1 d . . .
C4 C 0.24677(14) 0.7505(2) 0.8354(2) 0.0233(5) Uani 1 1 d . . .
H4 H 0.2154 0.8041 0.8881 0.028 Uiso 1 1 calc R . .
C9 C 0.62559(12) 0.7935(2) 0.63323(18) 0.0165(4) Uani 1 1 d . . .
C5 C 0.33369(13) 0.7741(2) 0.82376(19) 0.0205(5) Uani 1 1 d . . .
H5 H 0.3605 0.8439 0.8681 0.025 Uiso 1 1 calc R . .
C3 C 0.20624(13) 0.6478(2) 0.7692(2) 0.0226(5) Uani 1 1 d . . .
H3 H 0.1475 0.6340 0.7762 0.027 Uiso 1 1 calc R . .
O1 O 0.26307(8) 0.43259(16) 0.14875(13) 0.0191(3) Uani 1 1 d . . .
O3 O -0.06705(10) 0.79539(19) 0.04053(14) 0.0303(4) Uani 1 1 d . . .
H3O H -0.0994 0.8174 0.0945 0.045 Uiso 1 1 calc R . .
O2 O 0.18481(9) 0.37333(17) 0.30619(13) 0.0235(4) Uani 1 1 d . . .
C16 C 0.19380(13) 0.4381(2) 0.20881(19) 0.0194(5) Uani 1 1 d . . .
C12 C -0.00790(13) 0.6551(2) 0.20059(19) 0.0215(5) Uani 1 1 d . . .
H12 H -0.0514 0.6802 0.2521 0.026 Uiso 1 1 calc R . .
C10 C 0.12258(13) 0.5281(2) 0.16466(19) 0.0195(5) Uani 1 1 d . . .
C14 C 0.05802(14) 0.6684(3) 0.0080(2) 0.0284(6) Uani 1 1 d . . .
H14 H 0.0581 0.7013 -0.0707 0.034 Uiso 1 1 calc R . .
C11 C 0.05589(13) 0.5650(2) 0.2396(2) 0.0202(5) Uani 1 1 d . . .
H11 H 0.0542 0.5286 0.3170 0.024 Uiso 1 1 calc R . .
C15 C 0.12224(14) 0.5807(3) 0.0481(2) 0.0253(5) Uani 1 1 d . . .
H15 H 0.1659 0.5563 -0.0035 0.030 Uiso 1 1 calc R . .
C13 C -0.00679(13) 0.7078(2) 0.0846(2) 0.0221(5) Uani 1 1 d . . .
H4A H 0.6572(18) 0.660(3) 0.765(2) 0.043(8) Uiso 1 1 d . . .
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
Cl1 0.0222(3) 0.0236(3) 0.0256(3) -0.0032(2) 0.0079(2) -0.0008(2)
Cl2 0.0257(3) 0.0391(4) 0.0318(3) -0.0089(3) 0.0059(2) -0.0151(3)
N2 0.0137(8) 0.0179(10) 0.0191(9) 0.0003(8) 0.0020(7) -0.0002(7)
N1 0.0118(8) 0.0206(10) 0.0249(10) 0.0072(8) 0.0014(7) -0.0010(7)
N4 0.0122(9) 0.0234(11) 0.0203(10) 0.0034(8) 0.0015(7) 0.0008(7)
N3 0.0134(8) 0.0220(11) 0.0228(10) 0.0046(8) 0.0015(7) 0.0026(7)
C1 0.0189(10) 0.0192(12) 0.0166(11) 0.0046(9) 0.0038(8) 0.0015(9)
C7 0.0150(10) 0.0166(12) 0.0181(11) -0.0012(9) 0.0019(8) -0.0001(8)
C8 0.0156(10) 0.0167(11) 0.0174(11) -0.0026(9) 0.0018(8) -0.0029(8)
C2 0.0199(11) 0.0227(13) 0.0196(11) 0.0034(9) 0.0019(9) -0.0050(9)
C6 0.0156(10) 0.0194(12) 0.0185(11) 0.0052(9) 0.0009(8) -0.0018(8)
N5 0.0138(9) 0.0232(11) 0.0214(10) 0.0012(8) 0.0028(7) -0.0007(7)
C4 0.0218(11) 0.0271(14) 0.0211(12) 0.0019(10) 0.0072(9) 0.0031(10)
C9 0.0147(10) 0.0175(12) 0.0171(11) -0.0030(9) 0.0011(8) -0.0022(8)
C5 0.0219(11) 0.0210(12) 0.0187(11) 0.0019(9) 0.0024(9) -0.0023(9)
C3 0.0142(10) 0.0298(14) 0.0241(12) 0.0047(10) 0.0051(9) -0.0014(9)
O1 0.0094(7) 0.0257(9) 0.0223(8) -0.0010(7) 0.0040(6) 0.0023(6)
O3 0.0215(8) 0.0436(11) 0.0262(9) 0.0035(8) 0.0059(7) 0.0134(7)
O2 0.0156(7) 0.0312(9) 0.0239(8) 0.0058(7) 0.0053(6) 0.0023(6)
C16 0.0143(10) 0.0233(12) 0.0207(12) -0.0043(9) 0.0016(8) -0.0030(9)
C12 0.0132(10) 0.0272(13) 0.0242(12) -0.0040(10) 0.0065(9) -0.0002(9)
C10 0.0122(10) 0.0234(13) 0.0229(11) -0.0007(9) 0.0025(8) -0.0020(8)
C14 0.0235(12) 0.0401(15) 0.0220(12) 0.0082(11) 0.0070(9) 0.0078(10)
C11 0.0164(10) 0.0244(13) 0.0199(11) 0.0015(9) 0.0026(8) -0.0009(9)
C15 0.0163(11) 0.0348(15) 0.0251(12) 0.0029(10) 0.0081(9) 0.0064(10)
C13 0.0142(10) 0.0269(13) 0.0251(12) 0.0016(10) 0.0011(8) 0.0069(9)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.732(2) . ?
Cl2 C2 1.719(2) . ?
N2 C8 1.329(3) . ?
N2 C9 1.340(3) . ?
N1 C8 1.318(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N4 N5 1.355(2) . ?
N4 C9 1.356(3) . ?
N4 H4A 0.90(3) . ?
N3 C9 1.314(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C1 C2 1.393(3) . ?
C1 C6 1.396(3) . ?
C7 N5 1.293(3) . ?
C7 C8 1.455(3) . ?
C7 C6 1.485(3) . ?
C2 C3 1.382(3) . ?
C6 C5 1.394(3) . ?
C4 C3 1.381(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
O1 C16 1.283(2) . ?
O3 C13 1.349(3) . ?
O3 H3O 0.8200 . ?
O2 C16 1.261(3) . ?
C16 C10 1.486(3) . ?
C12 C11 1.385(3) . ?
C12 C13 1.387(3) . ?
C12 H12 0.9300 . ?
C10 C15 1.391(3) . ?
C10 C11 1.393(3) . ?
C14 C15 1.379(3) . ?
C14 C13 1.389(3) . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N2 C9 117.23(18) . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
N5 N4 C9 122.63(18) . . ?
N5 N4 H4A 113.1(18) . . ?
C9 N4 H4A 124.2(18) . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C2 C1 C6 120.0(2) . . ?
C2 C1 Cl1 120.60(17) . . ?
C6 C1 Cl1 119.43(16) . . ?
N5 C7 C8 121.25(18) . . ?
N5 C7 C6 120.88(19) . . ?
C8 C7 C6 117.79(17) . . ?
N1 C8 N2 119.79(19) . . ?
N1 C8 C7 120.17(18) . . ?
N2 C8 C7 120.03(18) . . ?
C3 C2 C1 119.9(2) . . ?
C3 C2 Cl2 119.24(16) . . ?
C1 C2 Cl2 120.84(17) . . ?
C5 C6 C1 119.46(19) . . ?
C5 C6 C7 120.75(19) . . ?
C1 C6 C7 119.04(19) . . ?
C7 N5 N4 116.89(18) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N3 C9 N2 120.08(19) . . ?
N3 C9 N4 118.24(18) . . ?
N2 C9 N4 121.67(18) . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C3 C2 120.24(19) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C13 O3 H3O 109.5 . . ?
O2 C16 O1 122.5(2) . . ?
O2 C16 C10 118.58(18) . . ?
O1 C16 C10 118.92(19) . . ?
C11 C12 C13 119.93(19) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C15 C10 C11 118.4(2) . . ?
C15 C10 C16 120.59(19) . . ?
C11 C10 C16 121.00(19) . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C14 C15 C10 120.9(2) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O3 C13 C12 123.04(19) . . ?
O3 C13 C14 117.4(2) . . ?
C12 C13 C14 119.5(2) . . ?
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
C9 N2 C8 N1 179.31(19) . . . . ?
C9 N2 C8 C7 -1.7(3) . . . . ?
N5 C7 C8 N1 -176.65(19) . . . . ?
C6 C7 C8 N1 6.7(3) . . . . ?
N5 C7 C8 N2 4.3(3) . . . . ?
C6 C7 C8 N2 -172.29(19) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
Cl1 C1 C2 C3 -178.98(17) . . . . ?
C6 C1 C2 Cl2 178.11(16) . . . . ?
Cl1 C1 C2 Cl2 -0.5(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
Cl1 C1 C6 C5 179.92(16) . . . . ?
C2 C1 C6 C7 -168.86(19) . . . . ?
Cl1 C1 C6 C7 9.8(3) . . . . ?
N5 C7 C6 C5 101.7(2) . . . . ?
C8 C7 C6 C5 -81.6(3) . . . . ?
N5 C7 C6 C1 -88.2(3) . . . . ?
C8 C7 C6 C1 88.4(2) . . . . ?
C8 C7 N5 N4 -1.7(3) . . . . ?
C6 C7 N5 N4 174.79(18) . . . . ?
C9 N4 N5 C7 -3.3(3) . . . . ?
C8 N2 C9 N3 177.84(19) . . . . ?
C8 N2 C9 N4 -3.3(3) . . . . ?
N5 N4 C9 N3 -174.98(19) . . . . ?
N5 N4 C9 N2 6.1(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C1 C6 C5 C4 -0.9(3) . . . . ?
C7 C6 C5 C4 169.1(2) . . . . ?
C5 C4 C3 C2 1.4(3) . . . . ?
C1 C2 C3 C4 -1.0(3) . . . . ?
Cl2 C2 C3 C4 -179.50(17) . . . . ?
O2 C16 C10 C15 -167.8(2) . . . . ?
O1 C16 C10 C15 14.5(3) . . . . ?
O2 C16 C10 C11 14.0(3) . . . . ?
O1 C16 C10 C11 -163.8(2) . . . . ?
C13 C12 C11 C10 1.2(3) . . . . ?
C15 C10 C11 C12 -1.9(3) . . . . ?
C16 C10 C11 C12 176.4(2) . . . . ?
C13 C14 C15 C10 1.2(4) . . . . ?
C11 C10 C15 C14 0.7(3) . . . . ?
C16 C10 C15 C14 -177.6(2) . . . . ?
C11 C12 C13 O3 179.7(2) . . . . ?
C11 C12 C13 C14 0.7(3) . . . . ?
C15 C14 C13 O3 179.1(2) . . . . ?
C15 C14 C13 C12 -1.9(4) . . . . ?
#===============================================================================
data_ltgaa
_database_code_depnum_ccdc_archive 'CCDC 819592'
#TrackingRef 'Finalltgaa.cif'
#===============================================================================
# 5. CHEMICAL DATA
_chemical_name_systematic
;
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C9 H8 Cl2 N5, 2(C2 H4 O2), C2 H3 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural ?
_chemical_formula_sum 'C15 H19 Cl2 N5 O6'
_chemical_formula_iupac ?
_chemical_formula_weight 436.25
_chemical_compound_source 'see text'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
#===============================================================================
# 6. CRYSTAL DATA
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 21/c'
_symmetry_Int_Tables_number 14
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z
_cell_length_a 7.0795(3)
_cell_length_b 17.7124(7)
_cell_length_c 15.9227(7)
_cell_angle_alpha 90
_cell_angle_beta 94.618(2)
_cell_angle_gamma 90
_cell_volume 1990.14(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 90(2)
_cell_measurement_reflns_used 11400
_cell_measurement_theta_min 1.7
_cell_measurement_theta_max 25.0
_cell_special_details
;
;
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.3
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.2
_exptl_crystal_size_rad ?
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.456
_exptl_crystal_density_method 'Not Measured'
_exptl_crystal_F_000 904
_exptl_absorpt_coefficient_mu 0.368
_exptl_crystal_density_meas_temp ?
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details 'CrysAlis RED (Oxford Diffraction,2009)'
_exptl_absorpt_correction_T_min 0.8975
_exptl_absorpt_correction_T_max 0.9299
#===============================================================================
# 7. EXPERIMENTAL DATA
_exptl_special_details
;
;
_diffrn_ambient_temperature 90(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Oxford Xcalibur,Eos(Nova) CCD detector'
_diffrn_measurement_method 'f\w scans'
_diffrn_reflns_number 11400
_diffrn_reflns_av_R_equivalents 0.0256
_diffrn_reflns_av_sigmaI/netI 0.0273
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -21
_diffrn_reflns_limit_k_max 19
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 1.72
_diffrn_reflns_theta_max 25.00
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_reduction_process
;
;
# number of unique reflections
_reflns_number_total 3498
# number of observed reflections (> n sig(I))
_reflns_number_gt 2969
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_cell_refinement 'CrysAlisPro CCD (Oxford Diffraction, 2009)'
_computing_data_reduction 'CrysAlisPro RED (Oxford Diffraction, 2009)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
'Ortep-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1993)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
#===============================================================================
# 8. REFINEMENT DATA
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+0.5395P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment mixed
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 3498
_refine_ls_number_parameters 268
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0388
_refine_ls_R_factor_gt 0.0301
_refine_ls_wR_factor_ref 0.0775
_refine_ls_wR_factor_gt 0.0747
_refine_ls_goodness_of_fit_ref 1.067
_refine_ls_restrained_S_all 1.067
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.229
_refine_diff_density_min -0.230
_refine_diff_density_rms 0.046
#===============================================================================
# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2 Cl 0.78734(6) 0.48867(2) 0.55262(3) 0.02815(13) Uani 1 1 d . . .
Cl1 Cl 0.91211(6) 0.32985(2) 0.49113(3) 0.02288(12) Uani 1 1 d . . .
O1 O 0.50015(16) 0.10556(7) 0.80275(8) 0.0236(3) Uani 1 1 d . . .
O2 O 0.26410(16) 0.12753(7) 0.70563(8) 0.0254(3) Uani 1 1 d . . .
O3 O 0.92716(17) 0.35329(7) 0.85409(7) 0.0231(3) Uani 1 1 d . . .
O4 O 0.95946(16) 0.31887(6) 0.72120(7) 0.0206(3) Uani 1 1 d . . .
O5 O 0.23098(15) 0.43113(7) 0.85595(7) 0.0226(3) Uani 1 1 d . . .
O6 O 0.40441(16) 0.52537(7) 0.81661(8) 0.0256(3) Uani 1 1 d . . .
N5 N 0.52212(18) 0.16609(8) 0.47728(9) 0.0169(3) Uani 1 1 d . . .
N4 N 0.56018(19) 0.09576(8) 0.45126(9) 0.0178(3) Uani 1 1 d . . .
N2 N 0.85493(18) 0.08915(7) 0.52962(8) 0.0153(3) Uani 1 1 d . . .
N1 N 0.93391(18) 0.18642(8) 0.62041(9) 0.0174(3) Uani 1 1 d . . .
H1A H 1.0320 0.1614 0.6399 0.021 Uiso 1 1 calc R . .
H1B H 0.9114 0.2303 0.6404 0.021 Uiso 1 1 calc R . .
N3 N 0.75408(19) -0.00646(8) 0.43800(9) 0.0195(3) Uani 1 1 d . . .
H3A H 0.8567 -0.0311 0.4516 0.023 Uiso 1 1 calc R . .
H3B H 0.6702 -0.0250 0.4016 0.023 Uiso 1 1 calc R . .
C3 C 0.4864(2) 0.41786(10) 0.60957(11) 0.0234(4) Uani 1 1 d . . .
H3 H 0.4504 0.4652 0.6280 0.028 Uiso 1 1 calc R . .
C4 C 0.3748(2) 0.35548(10) 0.62146(12) 0.0244(4) Uani 1 1 d . . .
H4 H 0.2621 0.3609 0.6471 0.029 Uiso 1 1 calc R . .
C5 C 0.4298(2) 0.28485(10) 0.59541(11) 0.0198(4) Uani 1 1 d . . .
H5 H 0.3536 0.2432 0.6037 0.024 Uiso 1 1 calc R . .
C6 C 0.5986(2) 0.27542(9) 0.55669(10) 0.0150(3) Uani 1 1 d . . .
C7 C 0.6486(2) 0.19861(9) 0.52850(10) 0.0149(3) Uani 1 1 d . . .
C9 C 0.7253(2) 0.05976(9) 0.47288(10) 0.0162(3) Uani 1 1 d . . .
C10 C 0.8734(2) 0.31699(9) 0.78452(11) 0.0183(4) Uani 1 1 d . . .
C2 C 0.6527(2) 0.40958(10) 0.56993(11) 0.0199(4) Uani 1 1 d . . .
C8 C 0.8182(2) 0.15740(9) 0.55997(10) 0.0144(3) Uani 1 1 d . . .
C1 C 0.7083(2) 0.33900(10) 0.54337(10) 0.0172(4) Uani 1 1 d . . .
C12 C 0.3370(2) 0.13621(9) 0.77718(12) 0.0204(4) Uani 1 1 d . . .
C13 C 0.2504(3) 0.18227(11) 0.84239(13) 0.0310(5) Uani 1 1 d . . .
H13A H 0.2764 0.2347 0.8335 0.046 Uiso 1 1 calc R . .
H13B H 0.3033 0.1674 0.8973 0.046 Uiso 1 1 calc R . .
H13C H 0.1159 0.1743 0.8383 0.046 Uiso 1 1 calc R . .
C11 C 0.6961(3) 0.27243(12) 0.79139(12) 0.0305(5) Uani 1 1 d . . .
H11A H 0.5905 0.3063 0.7931 0.046 Uiso 1 1 calc R . .
H11B H 0.7080 0.2427 0.8420 0.046 Uiso 1 1 calc R . .
H11C H 0.6758 0.2397 0.7435 0.046 Uiso 1 1 calc R . .
C14 C 0.2543(2) 0.48681(10) 0.80884(11) 0.0192(4) Uani 1 1 d . . .
C15 C 0.0992(2) 0.50765(10) 0.74301(11) 0.0234(4) Uani 1 1 d . . .
H15A H 0.0573 0.4633 0.7123 0.035 Uiso 1 1 calc R . .
H15B H 0.1463 0.5438 0.7049 0.035 Uiso 1 1 calc R . .
H15C H -0.0051 0.5292 0.7697 0.035 Uiso 1 1 calc R . .
H3O H 1.029(4) 0.3798(15) 0.8464(16) 0.064(8) Uiso 1 1 d . . .
H4A H 0.469(3) 0.0783(12) 0.4148(14) 0.041(6) Uiso 1 1 d . . .
H1O H 0.546(4) 0.0743(16) 0.7528(19) 0.079(9) Uiso 1 1 d . . .
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
Cl2 0.0341(2) 0.0166(2) 0.0326(3) 0.00288(19) -0.0044(2) -0.00431(18)
Cl1 0.0205(2) 0.0245(2) 0.0245(2) 0.00134(18) 0.00675(17) -0.00242(17)
O1 0.0201(6) 0.0243(7) 0.0254(7) -0.0012(6) -0.0043(5) 0.0021(5)
O2 0.0215(6) 0.0285(7) 0.0252(7) 0.0033(6) -0.0047(5) 0.0029(5)
O3 0.0233(6) 0.0286(7) 0.0175(7) -0.0077(6) 0.0027(5) -0.0063(6)
O4 0.0251(6) 0.0198(6) 0.0172(6) -0.0034(5) 0.0041(5) -0.0025(5)
O5 0.0215(6) 0.0225(7) 0.0226(7) 0.0027(6) -0.0051(5) -0.0007(5)
O6 0.0193(6) 0.0322(7) 0.0245(7) 0.0059(6) -0.0034(5) -0.0042(5)
N5 0.0179(7) 0.0167(8) 0.0163(7) -0.0011(6) 0.0017(6) -0.0014(6)
N4 0.0177(7) 0.0170(8) 0.0180(8) -0.0035(6) -0.0021(6) -0.0018(6)
N2 0.0180(6) 0.0146(7) 0.0132(7) -0.0010(6) 0.0014(6) -0.0018(6)
N1 0.0184(7) 0.0152(7) 0.0179(7) -0.0037(6) -0.0028(6) 0.0037(6)
N3 0.0222(7) 0.0164(8) 0.0192(8) -0.0037(6) -0.0027(6) -0.0006(6)
C3 0.0259(9) 0.0194(9) 0.0241(10) -0.0043(8) -0.0034(8) 0.0072(7)
C4 0.0191(8) 0.0280(10) 0.0263(10) -0.0025(8) 0.0024(7) 0.0056(8)
C5 0.0175(8) 0.0215(9) 0.0201(9) 0.0007(8) 0.0006(7) -0.0004(7)
C6 0.0161(7) 0.0169(9) 0.0115(8) 0.0008(7) -0.0025(6) 0.0021(7)
C7 0.0151(8) 0.0182(9) 0.0118(8) 0.0017(7) 0.0031(6) -0.0009(7)
C9 0.0202(8) 0.0166(9) 0.0121(8) 0.0021(7) 0.0030(7) -0.0013(7)
C10 0.0209(8) 0.0167(9) 0.0168(9) -0.0012(7) -0.0019(7) 0.0006(7)
C2 0.0239(8) 0.0166(9) 0.0178(9) 0.0021(7) -0.0065(7) -0.0005(7)
C8 0.0155(7) 0.0163(9) 0.0119(8) 0.0007(7) 0.0031(6) -0.0007(6)
C1 0.0157(7) 0.0216(9) 0.0140(8) 0.0009(7) -0.0012(6) 0.0017(7)
C12 0.0172(8) 0.0148(9) 0.0293(11) 0.0044(8) 0.0015(7) -0.0047(7)
C13 0.0253(9) 0.0294(11) 0.0385(12) -0.0045(9) 0.0044(9) 0.0011(8)
C11 0.0322(10) 0.0402(12) 0.0192(10) -0.0026(9) 0.0018(8) -0.0138(9)
C14 0.0190(8) 0.0199(9) 0.0185(9) -0.0042(8) 0.0003(7) 0.0029(7)
C15 0.0218(9) 0.0224(10) 0.0252(10) 0.0007(8) -0.0036(7) 0.0018(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2 C2 1.7289(17) . ?
Cl1 C1 1.7299(16) . ?
O1 C12 1.311(2) . ?
O1 H1O 1.04(3) . ?
O2 C12 1.222(2) . ?
O3 C10 1.311(2) . ?
O3 H3O 0.87(3) . ?
O4 C10 1.220(2) . ?
O5 C14 1.258(2) . ?
O6 C14 1.261(2) . ?
N5 C7 1.296(2) . ?
N5 N4 1.3468(19) . ?
N4 C9 1.351(2) . ?
N4 H4A 0.89(2) . ?
N2 C8 1.335(2) . ?
N2 C9 1.340(2) . ?
N1 C8 1.317(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N3 C9 1.321(2) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
C3 C4 1.380(3) . ?
C3 C2 1.388(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.398(2) . ?
C5 H5 0.9300 . ?
C6 C1 1.394(2) . ?
C6 C7 1.484(2) . ?
C7 C8 1.459(2) . ?
C10 C11 1.495(2) . ?
C2 C1 1.387(2) . ?
C12 C13 1.491(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 C15 1.501(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O1 H1O 107.6(15) . . ?
C10 O3 H3O 109.3(17) . . ?
C7 N5 N4 117.35(14) . . ?
N5 N4 C9 123.26(14) . . ?
N5 N4 H4A 111.8(14) . . ?
C9 N4 H4A 124.7(14) . . ?
C8 N2 C9 116.92(14) . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C4 C3 C2 119.58(16) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.32(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.74(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.51(15) . . ?
C1 C6 C7 123.02(14) . . ?
C5 C6 C7 118.42(14) . . ?
N5 C7 C8 120.08(15) . . ?
N5 C7 C6 115.35(14) . . ?
C8 C7 C6 124.36(14) . . ?
N3 C9 N2 120.53(15) . . ?
N3 C9 N4 118.14(15) . . ?
N2 C9 N4 121.32(15) . . ?
O4 C10 O3 123.72(15) . . ?
O4 C10 C11 123.60(15) . . ?
O3 C10 C11 112.68(15) . . ?
C1 C2 C3 120.40(16) . . ?
C1 C2 Cl2 120.53(13) . . ?
C3 C2 Cl2 119.05(13) . . ?
N1 C8 N2 119.34(14) . . ?
N1 C8 C7 120.13(14) . . ?
N2 C8 C7 120.50(14) . . ?
C2 C1 C6 120.42(15) . . ?
C2 C1 Cl1 119.95(13) . . ?
C6 C1 Cl1 119.61(13) . . ?
O2 C12 O1 122.21(16) . . ?
O2 C12 C13 123.48(16) . . ?
O1 C12 C13 114.31(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C14 O6 121.06(15) . . ?
O5 C14 C15 119.04(15) . . ?
O6 C14 C15 119.90(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
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
C7 N5 N4 C9 -3.1(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C4 C5 C6 C7 -178.81(15) . . . . ?
N4 N5 C7 C8 -3.9(2) . . . . ?
N4 N5 C7 C6 -178.85(13) . . . . ?
C1 C6 C7 N5 -121.42(17) . . . . ?
C5 C6 C7 N5 56.0(2) . . . . ?
C1 C6 C7 C8 63.9(2) . . . . ?
C5 C6 C7 C8 -118.71(17) . . . . ?
C8 N2 C9 N3 177.89(14) . . . . ?
C8 N2 C9 N4 -3.8(2) . . . . ?
N5 N4 C9 N3 -174.26(15) . . . . ?
N5 N4 C9 N2 7.3(2) . . . . ?
C4 C3 C2 C1 -0.9(3) . . . . ?
C4 C3 C2 Cl2 178.07(13) . . . . ?
C9 N2 C8 N1 174.99(14) . . . . ?
C9 N2 C8 C7 -3.1(2) . . . . ?
N5 C7 C8 N1 -170.86(15) . . . . ?
C6 C7 C8 N1 3.6(2) . . . . ?
N5 C7 C8 N2 7.2(2) . . . . ?
C6 C7 C8 N2 -178.30(14) . . . . ?
C3 C2 C1 C6 -0.5(3) . . . . ?
Cl2 C2 C1 C6 -179.39(12) . . . . ?
C3 C2 C1 Cl1 178.00(13) . . . . ?
Cl2 C2 C1 Cl1 -0.9(2) . . . . ?
C5 C6 C1 C2 1.5(2) . . . . ?
C7 C6 C1 C2 178.92(15) . . . . ?
C5 C6 C1 Cl1 -176.94(12) . . . . ?
C7 C6 C1 Cl1 0.5(2) . . . . ?
#===END