#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:14:47 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180295 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/09/7150907.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7150907
loop_
_publ_author_name
'Grabowsky, Simon'
'Pfeuffer, Thomas'
'Morgenroth, Wolfgang'
'Paulmann, Carsten'
'Schirmeister, Tanja'
'Luger, Peter'
_publ_contact_author
;
  Prof. Dr. Peter Luger
  Freie Universität Berlin
  Institut für Chemie und Biochemie
  Kristallographie
  Fabeckstr. 36a
  14195 Berlin
  Germany
;
_publ_section_title
;
 A comparative study on the experimentally derived electron densities
 of three protease inhibitor model compounds
;
_journal_issue                   13
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2295
_journal_page_last               2307
_journal_paper_doi               10.1039/b802831a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C12 H11 N O6'
_chemical_formula_sum            'C12 H11 N O6'
_chemical_formula_weight         265.22
_chemical_name_common            'acceptor-substituted olefin'
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                87.61(2)
_cell_angle_beta                 85.41(4)
_cell_angle_gamma                62.43(1)
_cell_formula_units_Z            2
_cell_length_a                   7.769(2)
_cell_length_b                   7.865(1)
_cell_length_c                   10.811(1)
_cell_measurement_reflns_used    3350
_cell_measurement_temperature    9
_cell_measurement_theta_max      31.61
_cell_measurement_theta_min      10.12
_cell_volume                     583.69(19)
_computing_cell_refinement
'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)'
_computing_data_collection
'XDS Kabsch, W. J. Appl. Cryst. 26, 795 (1993)'
_computing_data_reduction
'SORTAV Blessing, R. J. Appl. Cryst. 22, 396 (1989)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      9
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.902
_diffrn_measurement_device_type  'MarCCD 165 detector'
_diffrn_measurement_method       'phi scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.51660
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_sigmaI/netI    0.0459
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            104810
_diffrn_reflns_theta_full        20.15
_diffrn_reflns_theta_max         31.61
_diffrn_reflns_theta_min         1.37
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.092
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.468
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         7557
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.034
_refine_ls_R_factor_gt           0.027
_refine_ls_R_Fsqd_factor         0.049
_refine_ls_shift/su_max          0.00242
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.033
_reflns_number_gt                7557
_reflns_number_total             9203
_reflns_threshold_expression     >3sigma(I)
_cod_data_source_file            b802831a.txt
_cod_data_source_block           Olefin
_cod_original_cell_volume        583.7(2)
_cod_database_code               7150907
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O1 -0.52357(5) 0.71299(5) -0.18990(3) 1 2 0.010
O2 -0.41098(5) 0.48129(5) -0.32270(3) 1 2 0.010
O3 0.09381(5) 0.35765(5) 0.32816(3) 1 2 0.009
O4 -0.01277(5) 0.13505(5) 0.34696(3) 1 2 0.008
O5 0.56259(5) -0.18143(5) 0.17079(3) 1 2 0.009
O6 0.43757(5) -0.07003(4) 0.36257(3) 1 2 0.008
N2 -0.40670(5) 0.55028(5) -0.22390(3) 1 2 0.007
C1 0.21316(6) 0.08710(5) 0.07658(3) 1 2 0.007
C2 0.24200(5) 0.08068(5) 0.19811(3) 1 2 0.006
C3 0.04465(5) 0.21090(5) 0.00766(3) 1 2 0.006
C4 -0.11545(5) 0.37841(5) 0.05375(3) 1 2 0.007
C5 0.04981(5) 0.15634(5) -0.11519(3) 1 2 0.007
C6 -0.09913(5) 0.26493(5) -0.19085(3) 1 2 0.007
C7 -0.26466(5) 0.49004(5) -0.02163(3) 1 2 0.007
C8 -0.25338(5) 0.43115(5) -0.14257(3) 1 2 0.006
C9 0.10083(5) 0.20883(5) 0.29682(3) 1 2 0.006
C10 -0.15082(5) 0.24285(5) 0.44727(3) 1 2 0.010
C11 0.43120(5) -0.07037(5) 0.23938(3) 1 2 0.006
C12 0.61700(6) -0.21158(5) 0.41080(3) 1 2 0.011
H1 0.333169 -0.018858 0.02081 1 2 0.019(2)
H4 -0.123313 0.429791 0.146466 1 2 0.022(2)
H5 0.172615 0.026707 -0.150996 1 2 0.024(2)
H6 -0.095286 0.221429 -0.285191 1 2 0.021(2)
H7 -0.38509 0.623526 0.011299 1 2 0.027(2)
H10A -0.279787 0.348005 0.408334 1 2 0.036(2)
H10B -0.08693 0.307525 0.50022 1 2 0.040(2)
H10C -0.179578 0.139642 0.499423 1 2 0.035(2)
H12A 0.585694 -0.213512 0.50852 1 2 0.038(2)
H12B 0.656864 -0.347797 0.371245 1 2 0.044(3)
H12C 0.725706 -0.16585 0.390297 1 2 0.044(3)
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O4 C10 116.25(3) 1_555 1_555 1_555 yes
C11 O6 C12 115.32(3) 1_555 1_555 1_555 yes
O1 N2 O2 123.74(5) 1_555 1_555 1_555 yes
O1 N2 C8 118.43(4) 1_555 1_555 1_555 yes
O2 N2 C8 117.83(4) 1_555 1_555 1_555 yes
C2 C1 C3 130.89(3) 1_555 1_555 1_555 yes
C2 C1 H1 114.75 1_555 1_555 1_555 yes
C3 C1 H1 114.35 1_555 1_555 1_555 yes
C1 C2 C9 126.34(3) 1_555 1_555 1_555 yes
C1 C2 C11 117.18(3) 1_555 1_555 1_555 yes
C9 C2 C11 116.47(3) 1_555 1_555 1_555 yes
C1 C3 C4 125.22(3) 1_555 1_555 1_555 yes
C1 C3 C5 115.83(3) 1_555 1_555 1_555 yes
C4 C3 C5 118.93(4) 1_555 1_555 1_555 yes
C3 C4 C7 120.48(3) 1_555 1_555 1_555 yes
C3 C4 H4 121.72 1_555 1_555 1_555 yes
C7 C4 H4 117.70 1_555 1_555 1_555 yes
C3 C5 C6 121.19(3) 1_555 1_555 1_555 yes
C3 C5 H5 119.20 1_555 1_555 1_555 yes
C6 C5 H5 119.60 1_555 1_555 1_555 yes
C5 C6 C8 118.17(3) 1_555 1_555 1_555 yes
C5 C6 H6 120.93 1_555 1_555 1_555 yes
C8 C6 H6 120.90 1_555 1_555 1_555 yes
C4 C7 C8 118.68(3) 1_555 1_555 1_555 yes
C4 C7 H7 121.16 1_555 1_555 1_555 yes
C8 C7 H7 120.12 1_555 1_555 1_555 yes
N2 C8 C6 118.26(3) 1_555 1_555 1_555 yes
N2 C8 C7 119.18(3) 1_555 1_555 1_555 yes
C6 C8 C7 122.53(4) 1_555 1_555 1_555 yes
O3 C9 O4 124.76(4) 1_555 1_555 1_555 yes
O3 C9 C2 124.12(3) 1_555 1_555 1_555 yes
O4 C9 C2 111.10(3) 1_555 1_555 1_555 yes
O4 C10 H10A 108.42 1_555 1_555 1_555 yes
O4 C10 H10B 108.88 1_555 1_555 1_555 yes
O4 C10 H10C 104.79 1_555 1_555 1_555 yes
H10A C10 H10B 111.43 1_555 1_555 1_555 yes
H10A C10 H10C 110.50 1_555 1_555 1_555 yes
H10B C10 H10C 112.53 1_555 1_555 1_555 yes
O5 C11 O6 123.87(4) 1_555 1_555 1_555 yes
O5 C11 C2 124.57(4) 1_555 1_555 1_555 yes
O6 C11 C2 111.55(3) 1_555 1_555 1_555 yes
O6 C12 H12A 105.16 1_555 1_555 1_555 yes
O6 C12 H12B 109.44 1_555 1_555 1_555 yes
O6 C12 H12C 108.43 1_555 1_555 1_555 yes
H12A C12 H12B 110.87 1_555 1_555 1_555 yes
H12A C12 H12C 110.60 1_555 1_555 1_555 yes
H12B C12 H12C 112.08 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2278(5) 1_555 1_555 yes
O2 N2 1.2277(5) 1_555 1_555 yes
O3 C9 1.2078(5) 1_555 1_555 yes
O4 C9 1.3345(5) 1_555 1_555 yes
O4 C10 1.4470(5) 1_555 1_555 yes
O5 C11 1.2093(5) 1_555 1_555 yes
O6 C11 1.3368(5) 1_555 1_555 yes
O6 C12 1.4442(5) 1_555 1_555 yes
N2 C8 1.4613(5) 1_555 1_555 yes
C1 C2 1.3454(5) 1_555 1_555 yes
C1 C3 1.4604(5) 1_555 1_555 yes
C1 H1 1.0770 1_555 1_555 yes
C2 C9 1.4955(5) 1_555 1_555 yes
C2 C11 1.4883(5) 1_555 1_555 yes
C3 C4 1.4034(5) 1_555 1_555 yes
C3 C5 1.4045(5) 1_555 1_555 yes
C4 C7 1.3885(5) 1_555 1_555 yes
C4 H4 1.0830 1_555 1_555 yes
C5 C6 1.3841(5) 1_555 1_555 yes
C5 H5 1.0830 1_555 1_555 yes
C6 C8 1.3871(5) 1_555 1_555 yes
C6 H6 1.0830 1_555 1_555 yes
C7 C8 1.3879(5) 1_555 1_555 yes
C7 H7 1.0830 1_555 1_555 yes
C10 H10A 1.0660 1_555 1_555 yes
C10 H10B 1.0660 1_555 1_555 yes
C10 H10C 1.0660 1_555 1_555 yes
C12 H12A 1.0660 1_555 1_555 yes
C12 H12B 1.0660 1_555 1_555 yes
C12 H12C 1.0660 1_555 1_555 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O4 C9 O3 -1.02(4) 1_555 1_555 1_555 1_555 yes
C10 O4 C9 C2 177.69(4) 1_555 1_555 1_555 1_555 yes
C9 O4 C10 H10A 86.39 1_555 1_555 1_555 1_555 yes
C9 O4 C10 H10B -35.00 1_555 1_555 1_555 1_555 yes
C9 O4 C10 H10C -155.60 1_555 1_555 1_555 1_555 yes
C12 O6 C11 O5 1.17(4) 1_555 1_555 1_555 1_555 yes
C12 O6 C11 C2 -179.59(4) 1_555 1_555 1_555 1_555 yes
C11 O6 C12 H12A -167.18 1_555 1_555 1_555 1_555 yes
C11 O6 C12 H12B -48.04 1_555 1_555 1_555 1_555 yes
C11 O6 C12 H12C 74.49 1_555 1_555 1_555 1_555 yes
O1 N2 C8 C6 -166.84(5) 1_555 1_555 1_555 1_555 yes
O1 N2 C8 C7 11.66(4) 1_555 1_555 1_555 1_555 yes
O2 N2 C8 C6 13.15(4) 1_555 1_555 1_555 1_555 yes
O2 N2 C8 C7 -168.34(5) 1_555 1_555 1_555 1_555 yes
C2 C1 C3 C4 12.77(4) 1_555 1_555 1_555 1_555 yes
C2 C1 C3 C5 -168.75(6) 1_555 1_555 1_555 1_555 yes
C3 C1 C2 C9 -1.17(4) 1_555 1_555 1_555 1_555 yes
C3 C1 C2 C11 177.74(6) 1_555 1_555 1_555 1_555 yes
H1 C1 C2 C9 -179.60 1_555 1_555 1_555 1_555 yes
H1 C1 C2 C11 -0.70 1_555 1_555 1_555 1_555 yes
H1 C1 C3 C4 -168.79 1_555 1_555 1_555 1_555 yes
H1 C1 C3 C5 9.69 1_555 1_555 1_555 1_555 yes
C1 C2 C9 O3 -91.06(5) 1_555 1_555 1_555 1_555 yes
C1 C2 C9 O4 90.22(5) 1_555 1_555 1_555 1_555 yes
C1 C2 C11 O5 3.23(4) 1_555 1_555 1_555 1_555 yes
C1 C2 C11 O6 -176.00(5) 1_555 1_555 1_555 1_555 yes
C11 C2 C9 O3 90.03(5) 1_555 1_555 1_555 1_555 yes
C11 C2 C9 O4 -88.69(4) 1_555 1_555 1_555 1_555 yes
C9 C2 C11 O5 -177.76(5) 1_555 1_555 1_555 1_555 yes
C9 C2 C11 O6 3.01(3) 1_555 1_555 1_555 1_555 yes
C1 C3 C4 C7 177.36(6) 1_555 1_555 1_555 1_555 yes
C1 C3 C4 H4 1.10 1_555 1_555 1_555 1_555 yes
C1 C3 C5 C6 -178.34(5) 1_555 1_555 1_555 1_555 yes
C1 C3 C5 H5 1.80 1_555 1_555 1_555 1_555 yes
C4 C3 C5 C6 0.24(3) 1_555 1_555 1_555 1_555 yes
C5 C3 C4 C7 -1.08(3) 1_555 1_555 1_555 1_555 yes
C5 C3 C4 H4 -177.33 1_555 1_555 1_555 1_555 yes
C4 C3 C5 H5 -179.62 1_555 1_555 1_555 1_555 yes
C3 C4 C7 C8 0.87(3) 1_555 1_555 1_555 1_555 yes
C3 C4 C7 H7 -176.69 1_555 1_555 1_555 1_555 yes
H4 C4 C7 C8 177.28 1_555 1_555 1_555 1_555 yes
H4 C4 C7 H7 -0.28 1_555 1_555 1_555 1_555 yes
C3 C5 C6 C8 0.77(3) 1_555 1_555 1_555 1_555 yes
C3 C5 C6 H6 -179.31 1_555 1_555 1_555 1_555 yes
H5 C5 C6 C8 -179.37 1_555 1_555 1_555 1_555 yes
H5 C5 C6 H6 0.55 1_555 1_555 1_555 1_555 yes
C5 C6 C8 N2 177.45(5) 1_555 1_555 1_555 1_555 yes
C5 C6 C8 C7 -1.00(3) 1_555 1_555 1_555 1_555 yes
H6 C6 C8 N2 -2.47 1_555 1_555 1_555 1_555 yes
H6 C6 C8 C7 179.08 1_555 1_555 1_555 1_555 yes
C4 C7 C8 N2 -178.25(5) 1_555 1_555 1_555 1_555 yes
C4 C7 C8 C6 0.18(3) 1_555 1_555 1_555 1_555 yes
H7 C7 C8 N2 -0.67 1_555 1_555 1_555 1_555 yes
H7 C7 C8 C6 177.77 1_555 1_555 1_555 1_555 yes
