#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:13:01 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178840 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/94/4109400.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_4109400
loop_
_publ_author_name
'Leilani L. Welbes'
'Thomas W. Lyons'
'Katie A. Cychosz'
'Melanie S. Sanford'
_publ_section_title
;
 Synthesis of Cyclopropanes via Pd(II/IV)-Catalyzed Reactions of Enynes
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5836
_journal_page_last               5837
_journal_paper_doi               10.1021/ja071204j
_journal_volume                  129
_journal_year                    2007
_chemical_formula_moiety         'C13 H13 N O3'
_chemical_formula_sum            'C13 H13 N O3'
_chemical_formula_weight         231.24
_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                 102.627(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1687(15)
_cell_length_b                   11.3315(19)
_cell_length_c                   11.5459(19)
_cell_measurement_reflns_used    6349
_cell_measurement_temperature    108(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.23
_cell_volume                     1170.5(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART-1K'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      108(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0447
_diffrn_reflns_av_sigmaI/netI    0.0243
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24176
_diffrn_reflns_theta_full        27.34
_diffrn_reflns_theta_max         27.34
_diffrn_reflns_theta_min         2.28
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9616
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0557
_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)+(0.0939P)²+0.7675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1618
_refine_ls_wR_factor_ref         0.1749
_reflns_number_gt                2043
_reflns_number_total             2644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071204jsi20070217_015622.cif
_cod_data_source_block           tl129a
_cod_database_code               4109400
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
N1 N 0.7211(2) 0.43085(18) 0.32230(18) 0.0330(4) Uani 1 1 d .
O1 O 0.57677(19) 0.42849(15) 0.34545(15) 0.0369(4) Uani 1 1 d .
H1 H 0.527(4) 0.513(3) 0.315(3) 0.069(10) Uiso 1 1 d .
O2 O 0.56966(15) 0.13897(12) 0.23842(12) 0.0266(3) Uani 1 1 d .
O3 O 0.50326(16) 0.13279(14) 0.41201(13) 0.0328(4) Uani 1 1 d .
C1 C 0.7894(2) 0.33321(16) 0.35588(17) 0.0244(4) Uani 1 1 d .
C2 C 0.9430(2) 0.32795(17) 0.33609(17) 0.0254(4) Uani 1 1 d .
C3 C 1.0349(3) 0.42796(18) 0.3511(2) 0.0344(5) Uani 1 1 d .
H3A H 1.0002 0.4998 0.3779 0.041 Uiso 1 1 calc R
C4 C 1.1759(3) 0.4227(2) 0.3271(3) 0.0433(6) Uani 1 1 d .
H4A H 1.2374 0.4910 0.3377 0.052 Uiso 1 1 calc R
C5 C 1.2286(3) 0.3190(2) 0.2879(2) 0.0397(6) Uani 1 1 d .
H5A H 1.3249 0.3165 0.2702 0.048 Uiso 1 1 calc R
C6 C 1.1393(2) 0.2184(2) 0.2747(2) 0.0326(5) Uani 1 1 d .
H6A H 1.1749 0.1467 0.2484 0.039 Uiso 1 1 calc R
C7 C 0.9988(2) 0.22289(17) 0.29972(18) 0.0268(4) Uani 1 1 d .
H7A H 0.9393 0.1535 0.2921 0.032 Uiso 1 1 calc R
C8 C 0.7247(2) 0.23231(17) 0.41155(17) 0.0235(4) Uani 1 1 d .
C9 C 0.5959(2) 0.16567(18) 0.34216(18) 0.0269(4) Uani 1 1 d .
C10 C 0.5457(3) 0.1862(2) 0.53008(19) 0.0366(5) Uani 1 1 d .
H10A H 0.5497 0.1258 0.5927 0.044 Uiso 1 1 calc R
H10B H 0.4733 0.2481 0.5402 0.044 Uiso 1 1 calc R
C11 C 0.6967(2) 0.2381(2) 0.53591(18) 0.0319(5) Uani 1 1 d .
H11A H 0.7252 0.3115 0.5837 0.038 Uiso 1 1 calc R
C12 C 0.8173(2) 0.15962(19) 0.51274(18) 0.0288(5) Uani 1 1 d .
H12A H 0.9200 0.1918 0.5434 0.035 Uiso 1 1 calc R
C13 C 0.8102(3) 0.0265(2) 0.5158(2) 0.0383(6) Uani 1 1 d .
H13A H 0.8595 -0.0016 0.5949 0.058 Uiso 1 1 calc R
H13B H 0.8609 -0.0063 0.4567 0.058 Uiso 1 1 calc R
H13C H 0.7055 0.0011 0.4978 0.058 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
C1 N1 O1 110.0(2)
C9 O3 C10 111.69(17)
N1 C1 C2 113.90(18)
N1 C1 C8 124.98(19)
C2 C1 C8 121.12(16)
C7 C2 C3 118.5(2)
C7 C2 C1 120.39(17)
C3 C2 C1 121.13(18)
C4 C3 C2 120.3(2)
C3 C4 C5 120.8(2)
C4 C5 C6 119.5(2)
C7 C6 C5 119.9(2)
C6 C7 C2 120.98(19)
C9 C8 C1 120.09(16)
C9 C8 C11 104.76(16)
C1 C8 C11 122.64(17)
C9 C8 C12 112.53(17)
C1 C8 C12 122.31(17)
C11 C8 C12 58.60(13)
O2 C9 O3 120.68(18)
O2 C9 C8 128.82(18)
O3 C9 C8 110.49(17)
O3 C10 C11 105.07(16)
C12 C11 C10 118.3(2)
C12 C11 C8 61.11(13)
C10 C11 C8 106.74(17)
C11 C12 C13 123.71(19)
C11 C12 C8 60.28(13)
C13 C12 C8 122.49(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.288(3)
N1 O1 1.407(3)
O2 C9 1.207(2)
O3 C9 1.345(2)
O3 C10 1.464(3)
C1 C2 1.476(3)
C1 C8 1.496(3)
C2 C7 1.396(3)
C2 C3 1.400(3)
C3 C4 1.381(3)
C4 C5 1.384(4)
C5 C6 1.392(3)
C6 C7 1.381(3)
C8 C9 1.481(3)
C8 C11 1.514(3)
C8 C12 1.527(3)
C10 C11 1.492(3)
C11 C12 1.488(3)
C12 C13 1.511(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 1.08(4) 1.73(4) 2.804(2) 174(3) 2_655
