#------------------------------------------------------------------------------
#$Date: 2016-03-21 19:11:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178839 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/93/4109399.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_4109399
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         'C14 H13 N O5'
_chemical_formula_sum            'C14 H13 N O5'
_chemical_formula_weight         275.25
_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                 97.913(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8325(13)
_cell_length_b                   11.574(3)
_cell_length_c                   19.466(4)
_cell_measurement_reflns_used    9364
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      23.27
_cell_measurement_theta_min      2.49
_cell_volume                     1301.5(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(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  0.0337
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24785
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.9381
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Blessing, R. Acta Cryst. (1995) A51 33-38.
  Sheldrick, G.  SADABS (Version 2.10) Bruker/Siemens area
  detector absorption and other corrections, University of
  Gottingen, Germany 2003.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_description       needle
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0358
_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)+(0.0506P)²+0.5480P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1044
_reflns_number_gt                2578
_reflns_number_total             3235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja071204jsi20070217_015547.cif
_cod_data_source_block           lw264
_cod_database_code               4109399
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 0.94190(18) 0.57516(9) 0.43989(5) 0.0201(2) Uani 1 1 d .
O1 O 0.39694(16) 0.61117(9) 0.34328(5) 0.0291(2) Uani 1 1 d .
O2 O 0.49890(15) 0.47201(8) 0.27417(5) 0.0215(2) Uani 1 1 d .
O3 O 0.49931(18) 0.66512(10) 0.18349(6) 0.0376(3) Uani 1 1 d .
O4 O 0.80647(16) 0.75945(8) 0.15389(5) 0.0257(2) Uani 1 1 d .
O5 O 0.85781(17) 0.46302(8) 0.42463(5) 0.0250(2) Uani 1 1 d .
H5A H 0.904(3) 0.4275(17) 0.4674(11) 0.048(5) Uiso 1 1 d .
C1 C 0.5425(2) 0.56682(11) 0.31423(6) 0.0200(3) Uani 1 1 d .
C2 C 0.7054(2) 0.43284(11) 0.24715(7) 0.0216(3) Uani 1 1 d .
H2A H 0.6787 0.4312 0.1958 0.026 Uiso 1 1 calc R
H2B H 0.7480 0.3541 0.2642 0.026 Uiso 1 1 calc R
C3 C 0.8957(2) 0.51755(10) 0.27253(6) 0.0182(2) Uani 1 1 d .
H3A H 1.0543 0.4866 0.2884 0.022 Uiso 1 1 calc R
C4 C 0.7931(2) 0.60189(10) 0.31873(6) 0.0170(2) Uani 1 1 d .
C5 C 0.8716(2) 0.64363(11) 0.25169(6) 0.0188(2) Uani 1 1 d .
H5B H 1.0210 0.6873 0.2587 0.023 Uiso 1 1 calc R
C6 C 0.7021(2) 0.68813(11) 0.19346(6) 0.0210(3) Uani 1 1 d .
C7 C 0.6597(3) 0.81008(13) 0.09525(7) 0.0316(3) Uani 1 1 d .
H7A H 0.6611 0.7608 0.0544 0.047 Uiso 1 1 calc R
H7B H 0.7179 0.8870 0.0857 0.047 Uiso 1 1 calc R
H7C H 0.5010 0.8166 0.1061 0.047 Uiso 1 1 calc R
C8 C 0.9098(2) 0.64248(10) 0.38725(6) 0.0170(2) Uani 1 1 d .
C9 C 0.9874(2) 0.76343(10) 0.39871(6) 0.0178(2) Uani 1 1 d .
C10 C 0.8526(2) 0.85415(11) 0.36827(7) 0.0231(3) Uani 1 1 d .
H10A H 0.7155 0.8380 0.3374 0.028 Uiso 1 1 calc R
C11 C 0.9173(3) 0.96820(11) 0.38277(7) 0.0274(3) Uani 1 1 d .
H11A H 0.8232 1.0297 0.3626 0.033 Uiso 1 1 calc R
C12 C 1.1192(3) 0.99158(12) 0.42669(7) 0.0315(3) Uani 1 1 d .
H12A H 1.1631 1.0694 0.4370 0.038 Uiso 1 1 calc R
C13 C 1.2576(3) 0.90184(12) 0.45567(8) 0.0330(3) Uani 1 1 d .
H13A H 1.3973 0.9185 0.4852 0.040 Uiso 1 1 calc R
C14 C 1.1933(2) 0.78805(11) 0.44185(7) 0.0246(3) Uani 1 1 d .
H14A H 1.2891 0.7269 0.4617 0.029 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
C8 N1 O5 112.63(10)
C1 O2 C2 111.31(9)
C6 O4 C7 115.96(11)
O1 C1 O2 122.09(11)
O1 C1 C4 126.96(12)
O2 C1 C4 110.89(10)
O2 C2 C3 106.71(10)
C4 C3 C2 106.32(10)
C4 C3 C5 60.41(8)
C2 C3 C5 119.99(11)
C8 C4 C3 124.71(10)
C8 C4 C1 117.23(10)
C3 C4 C1 104.64(10)
C8 C4 C5 120.96(10)
C3 C4 C5 60.12(8)
C1 C4 C5 116.10(10)
C6 C5 C3 124.33(10)
C6 C5 C4 121.08(11)
C3 C5 C4 59.48(8)
O3 C6 O4 124.17(12)
O3 C6 C5 125.56(12)
O4 C6 C5 110.26(11)
N1 C8 C9 116.59(11)
N1 C8 C4 121.58(11)
C9 C8 C4 121.80(10)
C10 C9 C14 119.33(12)
C10 C9 C8 120.40(11)
C14 C9 C8 120.24(11)
C11 C10 C9 120.47(12)
C12 C11 C10 119.67(12)
C11 C12 C13 120.22(13)
C14 C13 C12 120.40(13)
C13 C14 C9 119.85(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C8 1.2803(16)
N1 O5 1.4047(13)
O1 C1 1.1985(16)
O2 C1 1.3500(15)
O2 C2 1.4515(15)
O3 C6 1.2021(16)
O4 C6 1.3319(16)
O4 C7 1.4526(16)
C1 C4 1.5076(16)
C2 C3 1.5123(17)
C3 C4 1.5061(17)
C3 C5 1.5159(17)
C4 C8 1.4877(16)
C4 C5 1.5203(16)
C5 C6 1.4896(17)
C8 C9 1.4787(17)
C9 C10 1.3941(17)
C9 C14 1.3969(18)
C10 C11 1.3911(19)
C11 C12 1.383(2)
C12 C13 1.387(2)
C13 C14 1.3855(19)
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
O5 H5A N1 0.93(2) 1.90(2) 2.7688(15) 153.2(18) 3_766
