#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/34/4023417.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_4023417
loop_
_publ_author_name
'Ni Yan'
'Xiaozhong Liu'
'Mahesh K. Pallerla'
'Joseph M. Fox'
_publ_section_title
;
 Synthesis of Stable Derivatives of Cycloprop-2-ene Carboxylic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4283
_journal_page_last               4286
_journal_paper_doi               10.1021/jo800042w
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C13 H11 N O3'
_chemical_formula_weight         229.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.037(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2085(13)
_cell_length_b                   7.4494(12)
_cell_length_c                   9.1771(14)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.37
_cell_measurement_theta_min      2.53
_cell_volume                     550.79(15)
_computing_cell_refinement       'SHELXTL, Sheldrick (2001)'
_computing_data_collection       'SMART, Bruker (2002)'
_computing_data_reduction        'SHELXTL, Sheldrick (2001)'
_computing_molecular_graphics    'SHELXTL, Sheldrick (2001)'
_computing_publication_material  'SHELXTL, Sheldrick (2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device_type  'Bruker AXS APEX diffractometer'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0263
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5947
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.85
_diffrn_reflns_theta_min         2.26
_diffrn_standards_decay_%        <1
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9970
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.6(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2380
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0720P)²+0.0883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1063
_reflns_number_gt                2316
_reflns_number_total             2380
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo800042w-File001.cif
_cod_data_source_block           joef014
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023417
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
N1 N -0.05132(18) 0.4869(2) 0.23301(16) 0.0173(3) Uani 1 1 d . . .
O1 O 0.04109(15) 0.76594(18) 0.21425(13) 0.0210(3) Uani 1 1 d . . .
O2 O -0.17272(16) 0.67850(19) 0.04096(13) 0.0235(3) Uani 1 1 d . . .
O3 O -0.17007(15) 0.24954(18) 0.32204(13) 0.0230(3) Uani 1 1 d . . .
C1 C 0.2315(2) 0.2451(3) 0.32225(19) 0.0210(4) Uani 1 1 d . . .
H1A H 0.1901 0.2604 0.2190 0.025 Uiso 1 1 calc R . .
C2 C 0.3427(2) 0.1083(3) 0.3710(2) 0.0225(4) Uani 1 1 d . . .
H2A H 0.3778 0.0307 0.3009 0.027 Uiso 1 1 calc R . .
C3 C 0.4034(2) 0.0835(3) 0.5216(2) 0.0224(4) Uani 1 1 d . . .
H3A H 0.4775 -0.0125 0.5547 0.027 Uiso 1 1 calc R . .
C4 C 0.3551(2) 0.1999(3) 0.62317(19) 0.0205(4) Uani 1 1 d . . .
H4A H 0.3984 0.1853 0.7261 0.025 Uiso 1 1 calc R . .
C5 C 0.2432(2) 0.3384(2) 0.57516(19) 0.0179(4) Uani 1 1 d . . .
H5A H 0.2102 0.4175 0.6454 0.022 Uiso 1 1 calc R . .
C6 C 0.1800(2) 0.3605(2) 0.42425(19) 0.0162(3) Uani 1 1 d . . .
C7 C 0.0635(2) 0.5158(2) 0.37528(18) 0.0164(3) Uani 1 1 d . . .
H7A H -0.0006 0.5448 0.4546 0.020 Uiso 1 1 calc R . .
C8 C 0.1545(2) 0.6837(3) 0.33645(19) 0.0224(4) Uani 1 1 d . . .
H8A H 0.1788 0.7663 0.4224 0.027 Uiso 1 1 calc R . .
H8B H 0.2601 0.6508 0.3062 0.027 Uiso 1 1 calc R . .
C9 C -0.0712(2) 0.6451(2) 0.15017(18) 0.0184(4) Uani 1 1 d . . .
C10 C -0.1618(2) 0.3404(2) 0.21471(18) 0.0178(3) Uani 1 1 d . . .
C11 C -0.2513(2) 0.2983(2) 0.0620(2) 0.0207(4) Uani 1 1 d . . .
H11A H -0.2310 0.3754 -0.0219 0.025 Uiso 1 1 calc R . .
C12 C -0.2905(3) 0.1014(3) 0.0325(2) 0.0288(4) Uani 1 1 d . . .
H12A H -0.2501 -0.0149 0.0158 0.035 Uiso 1 1 calc R . .
C13 C -0.4134(2) 0.1977(3) 0.0451(2) 0.0303(5) Uani 1 1 d . . .
H13A H -0.5291 0.2031 0.0444 0.036 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
C9 N1 C10 125.77(14) . . ?
C9 N1 C7 110.35(14) . . ?
C10 N1 C7 120.48(14) . . ?
C9 O1 C8 109.96(14) . . ?
C2 C1 C6 120.17(16) . . ?
C1 C2 C3 120.59(17) . . ?
C4 C3 C2 119.44(17) . . ?
C3 C4 C5 120.41(16) . . ?
C6 C5 C4 119.93(16) . . ?
C5 C6 C1 119.43(16) . . ?
C5 C6 C7 118.67(15) . . ?
C1 C6 C7 121.83(15) . . ?
N1 C7 C6 114.37(14) . . ?
N1 C7 C8 99.83(13) . . ?
C6 C7 C8 112.59(14) . . ?
O1 C8 C7 104.79(13) . . ?
O2 C9 O1 122.43(16) . . ?
O2 C9 N1 128.30(17) . . ?
O1 C9 N1 109.23(14) . . ?
O3 C10 N1 118.20(15) . . ?
O3 C10 C11 123.80(16) . . ?
N1 C10 C11 117.82(15) . . ?
C10 C11 C13 117.96(16) . . ?
C10 C11 C12 115.01(15) . . ?
C13 C11 C12 49.29(13) . . ?
C13 C12 C11 65.11(15) . . ?
C12 C13 C11 65.59(14) . . ?
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
N1 C9 1.395(2) . ?
N1 C10 1.408(2) . ?
N1 C7 1.473(2) . ?
O1 C9 1.341(2) . ?
O1 C8 1.449(2) . ?
O2 C9 1.201(2) . ?
O3 C10 1.208(2) . ?
C1 C2 1.384(3) . ?
C1 C6 1.395(2) . ?
C2 C3 1.389(3) . ?
C3 C4 1.386(3) . ?
C4 C5 1.395(2) . ?
C5 C6 1.393(2) . ?
C6 C7 1.513(2) . ?
C7 C8 1.533(3) . ?
C10 C11 1.486(2) . ?
C11 C13 1.509(3) . ?
C11 C12 1.515(3) . ?
C12 C13 1.261(3) . ?
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 0.4(3) . . . . ?
C1 C2 C3 C4 -1.6(3) . . . . ?
C2 C3 C4 C5 1.6(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.9(2) . . . . ?
C4 C5 C6 C7 -177.94(15) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
C2 C1 C6 C7 177.76(16) . . . . ?
C9 N1 C7 C6 -141.17(14) . . . . ?
C10 N1 C7 C6 58.5(2) . . . . ?
C9 N1 C7 C8 -20.74(17) . . . . ?
C10 N1 C7 C8 178.91(15) . . . . ?
C5 C6 C7 N1 -154.24(15) . . . . ?
C1 C6 C7 N1 28.8(2) . . . . ?
C5 C6 C7 C8 92.71(18) . . . . ?
C1 C6 C7 C8 -84.2(2) . . . . ?
C9 O1 C8 C7 -19.38(18) . . . . ?
N1 C7 C8 O1 23.24(16) . . . . ?
C6 C7 C8 O1 144.96(14) . . . . ?
C8 O1 C9 O2 -175.64(15) . . . . ?
C8 O1 C9 N1 6.34(18) . . . . ?
C10 N1 C9 O2 -8.6(3) . . . . ?
C7 N1 C9 O2 -167.65(17) . . . . ?
C10 N1 C9 O1 169.30(15) . . . . ?
C7 N1 C9 O1 10.23(18) . . . . ?
C9 N1 C10 O3 -150.54(17) . . . . ?
C7 N1 C10 O3 6.6(2) . . . . ?
C9 N1 C10 C11 34.2(2) . . . . ?
C7 N1 C10 C11 -168.68(15) . . . . ?
O3 C10 C11 C13 29.1(3) . . . . ?
N1 C10 C11 C13 -155.92(16) . . . . ?
O3 C10 C11 C12 -26.4(3) . . . . ?
N1 C10 C11 C12 148.63(17) . . . . ?
C10 C11 C12 C13 106.33(19) . . . . ?
C10 C11 C13 C12 -100.06(19) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658673
