#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:35:02 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180306 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/20/7152071.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_7152071
loop_
_publ_author_name
'Patel, Pitambar'
'Ramana, Chepuri V.'
_publ_section_title
;
 Divergent Pd(ii) and Au(iii) mediated nitroalkynol cycloisomerizations.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7327
_journal_page_last               7334
_journal_paper_doi               10.1039/c0ob00858c
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C13 H15 N O2'
_chemical_formula_sum            'C13 H15 N O2'
_chemical_formula_weight         217.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 92.446(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.863(4)
_cell_length_b                   9.081(3)
_cell_length_c                   10.470(4)
_cell_measurement_reflns_used    2820
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      26.99
_cell_measurement_theta_min      2.825
_cell_volume                     1126.9(7)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL, Ortep32'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      297(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       'Phi and Omega Scan'
_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  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7790
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9957
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         1983
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0459
_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)+(0.0502P)²+0.3234P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1140
_refine_ls_wR_factor_ref         0.1194
_reflns_number_gt                1729
_reflns_number_total             1983
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob00858c.txt
_cod_data_source_block           ptmb15
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P21/C
_cod_database_code               7152071
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O1 O 0.18010(10) 0.18065(14) 0.26219(11) 0.0498(4) Uani 1 1 d .
O2 O 0.27518(12) 0.45812(15) 0.32114(12) 0.0587(4) Uani 1 1 d .
N1 N 0.29940(12) 0.18544(16) 0.08444(15) 0.0434(4) Uani 1 1 d .
C2 C 0.22446(14) 0.26887(19) 0.16407(15) 0.0396(4) Uani 1 1 d .
C3 C 0.30415(15) 0.38073(19) 0.23282(16) 0.0426(4) Uani 1 1 d .
C4 C 0.41100(15) 0.36962(19) 0.17363(15) 0.0405(4) Uani 1 1 d .
C5 C 0.40394(14) 0.25436(18) 0.08580(15) 0.0371(4) Uani 1 1 d .
C6 C 0.13094(16) 0.3487(2) 0.08777(19) 0.0484(5) Uani 1 1 d .
C7 C 0.03900(19) 0.2440(3) 0.0385(2) 0.0622(6) Uani 1 1 d .
C8 C -0.00046(19) 0.1503(3) 0.1474(2) 0.0643(6) Uani 1 1 d .
C9 C 0.09895(19) 0.0755(3) 0.2138(2) 0.0600(6) Uani 1 1 d .
C10 C 0.51168(17) 0.4487(2) 0.19153(18) 0.0520(5) Uani 1 1 d .
C11 C 0.60192(17) 0.4113(2) 0.12184(19) 0.0553(5) Uani 1 1 d .
C12 C 0.59543(15) 0.2948(2) 0.03309(18) 0.0476(5) Uani 1 1 d .
C13 C 0.49608(15) 0.2171(2) 0.01480(17) 0.0422(4) Uani 1 1 d .
C14 C 0.69689(17) 0.2544(3) -0.0411(2) 0.0690(6) Uani 1 1 d .
H14A H 0.6980 0.1498 -0.0546 0.103 Uiso 1 1 calc R
H14B H 0.7643 0.2837 0.0061 0.103 Uiso 1 1 calc R
H14C H 0.6930 0.3038 -0.1222 0.103 Uiso 1 1 calc R
H1 H 0.2704(17) 0.146(2) 0.011(2) 0.059(6) Uiso 1 1 d .
H6A H 0.1623(17) 0.403(2) 0.021(2) 0.057(6) Uiso 1 1 d .
H6B H 0.1001(16) 0.421(2) 0.1449(18) 0.049(5) Uiso 1 1 d .
H7A H 0.0697(19) 0.183(2) -0.029(2) 0.065(6) Uiso 1 1 d .
H7B H -0.024(2) 0.303(2) -0.004(2) 0.074(7) Uiso 1 1 d .
H8A H -0.0389(17) 0.210(2) 0.209(2) 0.059(6) Uiso 1 1 d .
H8B H -0.055(2) 0.077(3) 0.118(2) 0.079(7) Uiso 1 1 d .
H9A H 0.0775(18) 0.021(2) 0.287(2) 0.066(6) Uiso 1 1 d .
H9B H 0.1360(17) 0.006(2) 0.152(2) 0.062(6) Uiso 1 1 d .
H10 H 0.5145(18) 0.528(3) 0.252(2) 0.068(6) Uiso 1 1 d .
H11 H 0.6733(19) 0.464(2) 0.1332(19) 0.065(6) Uiso 1 1 d .
H13 H 0.4885(15) 0.139(2) -0.0446(18) 0.050(5) Uiso 1 1 d .
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
C2 O1 C9 112.57(14)
C5 N1 C2 109.04(14)
O1 C2 N1 111.98(14)
O1 C2 C6 111.33(14)
N1 C2 C6 113.33(14)
O1 C2 C3 105.78(13)
N1 C2 C3 103.44(13)
C6 C2 C3 110.42(15)
O2 C3 C4 130.38(17)
O2 C3 C2 122.98(16)
C4 C3 C2 106.63(14)
C5 C4 C10 120.06(17)
C5 C4 C3 107.93(15)
C10 C4 C3 132.00(17)
N1 C5 C13 127.39(16)
N1 C5 C4 111.95(15)
C13 C5 C4 120.62(16)
C7 C6 C2 112.09(17)
C8 C7 C6 109.66(18)
C9 C8 C7 109.90(18)
O1 C9 C8 111.34(19)
C11 C10 C4 119.02(19)
C10 C11 C12 121.21(18)
C13 C12 C11 119.87(18)
C13 C12 C14 120.04(19)
C11 C12 C14 120.08(18)
C12 C13 C5 119.21(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.4214(19)
O1 C9 1.433(2)
O2 C3 1.222(2)
N1 C5 1.389(2)
N1 C2 1.457(2)
C2 C6 1.523(3)
C2 C3 1.545(2)
C3 C4 1.438(2)
C4 C5 1.394(2)
C4 C10 1.399(3)
C5 C13 1.390(2)
C6 C7 1.521(3)
C7 C8 1.513(3)
C8 C9 1.505(3)
C10 C11 1.364(3)
C11 C12 1.408(3)
C12 C13 1.380(3)
C12 C14 1.506(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
C9 O1 C2 N1 -71.24(19)
C9 O1 C2 C6 56.8(2)
C9 O1 C2 C3 176.76(15)
C5 N1 C2 O1 -123.40(15)
C5 N1 C2 C6 109.64(17)
C5 N1 C2 C3 -9.95(17)
O1 C2 C3 O2 -52.1(2)
N1 C2 C3 O2 -170.00(16)
C6 C2 C3 O2 68.4(2)
O1 C2 C3 C4 126.96(14)
N1 C2 C3 C4 9.09(17)
C6 C2 C3 C4 -112.47(16)
O2 C3 C4 C5 173.93(18)
C2 C3 C4 C5 -5.07(18)
O2 C3 C4 C10 -4.9(3)
C2 C3 C4 C10 176.06(18)
C2 N1 C5 C13 -174.59(16)
C2 N1 C5 C4 7.50(19)
C10 C4 C5 N1 177.77(15)
C3 C4 C5 N1 -1.25(19)
C10 C4 C5 C13 -0.3(3)
C3 C4 C5 C13 -179.32(15)
O1 C2 C6 C7 -52.4(2)
N1 C2 C6 C7 74.9(2)
C3 C2 C6 C7 -169.61(16)
C2 C6 C7 C8 51.1(2)
C6 C7 C8 C9 -53.6(3)
C2 O1 C9 C8 -60.7(2)
C7 C8 C9 O1 58.6(3)
C5 C4 C10 C11 0.1(3)
C3 C4 C10 C11 178.84(18)
C4 C10 C11 C12 -0.2(3)
C10 C11 C12 C13 0.5(3)
C10 C11 C12 C14 -179.08(19)
C11 C12 C13 C5 -0.7(3)
C14 C12 C13 C5 178.89(17)
N1 C5 C13 C12 -177.12(16)
C4 C5 C13 C12 0.6(3)
