#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502845.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_1502845
loop_
_publ_author_name
'Mondal, Mukulesh'
'Ibrahim, Ahmad A.'
'Wheeler, Kraig A.'
'Kerrigan, Nessan J.'
_publ_section_title
;
 Phosphine-catalyzed asymmetric synthesis of beta-lactones from
 arylketoketenes and aromatic aldehydes.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1664
_journal_page_last               1667
_journal_paper_doi               10.1021/ol100075m
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C16 H13 N O4'
_chemical_formula_sum            'C16 H13 N O4'
_chemical_formula_weight         283.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.6054(4)
_cell_length_b                   7.0101(1)
_cell_length_c                   15.5516(2)
_cell_measurement_reflns_used    4284
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.566
_cell_measurement_theta_min      3.507
_cell_volume                     2682.44(7)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction
;
SAINT (Bruker, 2008) and XPREP (Bruker, 2008)
;
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14868
_diffrn_reflns_theta_full        68.19
_diffrn_reflns_theta_max         68.19
_diffrn_reflns_theta_min         3.59
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_T_max  0.9278
_exptl_absorpt_correction_T_min  0.7665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'transparent needle'
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0391
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.7123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.1037
_reflns_number_gt                1843
_reflns_number_total             2392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100075m_si_003.cif
_cod_data_source_block           nker01
_cod_database_code               1502845
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'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 0.59128(5) 0.20915(17) 0.88318(8) 0.0284(3) Uani 1 1 d .
O2 O 0.67093(6) 0.05106(19) 0.85968(8) 0.0358(3) Uani 1 1 d .
O3 O 0.52573(6) 0.7966(2) 1.22741(8) 0.0367(4) Uani 1 1 d .
O4 O 0.53880(6) 1.0483(2) 1.14947(8) 0.0348(3) Uani 1 1 d .
N1 N 0.53697(6) 0.8754(2) 1.15881(9) 0.0282(4) Uani 1 1 d .
C1 C 0.64462(8) 0.1946(3) 0.86051(11) 0.0284(4) Uani 1 1 d .
C2 C 0.65289(7) 0.4058(3) 0.84292(11) 0.0261(4) Uani 1 1 d .
C3 C 0.59127(7) 0.4173(2) 0.86756(11) 0.0256(4) Uani 1 1 d .
H3 H 0.5683 0.4513 0.8167 0.031 Uiso 1 1 calc R
C4 C 0.69259(8) 0.4999(3) 0.90607(11) 0.0304(4) Uani 1 1 d .
H4A H 0.6829 0.4640 0.9650 0.046 Uiso 1 1 calc R
H4B H 0.6906 0.6388 0.9000 0.046 Uiso 1 1 calc R
H4C H 0.7297 0.4569 0.8936 0.046 Uiso 1 1 calc R
C5 C 0.57547(7) 0.5306(3) 0.94534(10) 0.0243(4) Uani 1 1 d .
C6 C 0.56884(7) 0.4477(3) 1.02624(11) 0.0259(4) Uani 1 1 d .
H6 H 0.5738 0.3142 1.0332 0.031 Uiso 1 1 calc R
C7 C 0.55498(7) 0.5591(3) 1.09655(11) 0.0263(4) Uani 1 1 d .
H7 H 0.5495 0.5033 1.1515 0.032 Uiso 1 1 calc R
C8 C 0.54939(7) 0.7529(3) 1.08453(11) 0.0252(4) Uani 1 1 d .
C9 C 0.55623(7) 0.8396(3) 1.00524(11) 0.0260(4) Uani 1 1 d .
H9 H 0.5525 0.9738 0.9991 0.031 Uiso 1 1 calc R
C10 C 0.56859(7) 0.7260(3) 0.93515(11) 0.0253(4) Uani 1 1 d .
H10 H 0.5724 0.7819 0.8798 0.030 Uiso 1 1 calc R
C11 C 0.66617(7) 0.4588(3) 0.75036(11) 0.0267(4) Uani 1 1 d .
C12 C 0.66823(8) 0.6494(3) 0.72724(12) 0.0322(4) Uani 1 1 d .
H12 H 0.6617 0.7449 0.7693 0.039 Uiso 1 1 calc R
C13 C 0.67970(8) 0.7022(3) 0.64314(12) 0.0361(5) Uani 1 1 d .
H13 H 0.6809 0.8334 0.6280 0.043 Uiso 1 1 calc R
C14 C 0.68930(8) 0.5654(3) 0.58158(12) 0.0373(5) Uani 1 1 d .
H14 H 0.6973 0.6015 0.5241 0.045 Uiso 1 1 calc R
C15 C 0.68727(10) 0.3773(3) 0.60407(13) 0.0468(6) Uani 1 1 d .
H15 H 0.6937 0.2825 0.5616 0.056 Uiso 1 1 calc R
C16 C 0.67595(9) 0.3222(3) 0.68835(12) 0.0401(5) Uani 1 1 d .
H16 H 0.6750 0.1907 0.7031 0.048 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 O1 C3 91.82(13)
O4 N1 O3 123.79(15)
O4 N1 C8 118.56(15)
O3 N1 C8 117.65(16)
O2 C1 O1 125.94(18)
O2 C1 C2 138.16(18)
O1 C1 C2 95.88(14)
C1 C2 C11 115.91(15)
C1 C2 C4 112.89(15)
C11 C2 C4 111.33(15)
C1 C2 C3 82.89(13)
C11 C2 C3 115.26(15)
C4 C2 C3 115.96(15)
O1 C3 C5 112.99(14)
O1 C3 C2 89.39(13)
C5 C3 C2 118.41(15)
O1 C3 H3 111.4
C5 C3 H3 111.4
C2 C3 H3 111.4
C2 C4 H4A 109.5
C2 C4 H4B 109.5
H4A C4 H4B 109.5
C2 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 C5 C6 119.94(16)
C10 C5 C3 117.54(15)
C6 C5 C3 122.50(16)
C7 C6 C5 120.36(17)
C7 C6 H6 119.8
C5 C6 H6 119.8
C8 C7 C6 118.21(16)
C8 C7 H7 120.9
C6 C7 H7 120.9
C7 C8 C9 122.77(16)
C7 C8 N1 119.31(16)
C9 C8 N1 117.90(16)
C10 C9 C8 118.38(17)
C10 C9 H9 120.8
C8 C9 H9 120.8
C9 C10 C5 120.29(16)
C9 C10 H10 119.9
C5 C10 H10 119.9
C16 C11 C12 118.81(17)
C16 C11 C2 121.90(17)
C12 C11 C2 119.29(16)
C11 C12 C13 120.62(18)
C11 C12 H12 119.7
C13 C12 H12 119.7
C14 C13 C12 120.34(19)
C14 C13 H13 119.8
C12 C13 H13 119.8
C15 C14 C13 119.25(19)
C15 C14 H14 120.4
C13 C14 H14 120.4
C14 C15 C16 121.06(19)
C14 C15 H15 119.5
C16 C15 H15 119.5
C11 C16 C15 119.9(2)
C11 C16 H16 120.0
C15 C16 H16 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.363(2)
O1 C3 1.479(2)
O2 C1 1.196(2)
O3 N1 1.2330(19)
O4 N1 1.221(2)
N1 C8 1.472(2)
C1 C2 1.520(3)
C2 C11 1.522(2)
C2 C4 1.534(2)
C2 C3 1.566(3)
C3 C5 1.498(2)
C3 H3 1.0000
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C10 1.390(3)
C5 C6 1.395(2)
C6 C7 1.386(2)
C6 H6 0.9500
C7 C8 1.379(3)
C7 H7 0.9500
C8 C9 1.385(2)
C9 C10 1.384(2)
C9 H9 0.9500
C10 H10 0.9500
C11 C16 1.381(3)
C11 C12 1.384(3)
C12 C13 1.388(3)
C12 H12 0.9500
C13 C14 1.375(3)
C13 H13 0.9500
C14 C15 1.365(3)
C14 H14 0.9500
C15 C16 1.395(3)
C15 H15 0.9500
C16 H16 0.9500
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
C3 O1 C1 O2 179.90(18)
C3 O1 C1 C2 1.09(13)
O2 C1 C2 C11 65.7(3)
O1 C1 C2 C11 -115.71(16)
O2 C1 C2 C4 -64.4(3)
O1 C1 C2 C4 114.19(15)
O2 C1 C2 C3 -179.6(2)
O1 C1 C2 C3 -1.04(13)
C1 O1 C3 C5 -121.88(15)
C1 O1 C3 C2 -1.06(13)
C1 C2 C3 O1 0.95(12)
C11 C2 C3 O1 116.30(15)
C4 C2 C3 O1 -111.09(16)
C1 C2 C3 C5 116.95(16)
C11 C2 C3 C5 -127.70(17)
C4 C2 C3 C5 4.9(2)
O1 C3 C5 C10 -173.34(15)
C2 C3 C5 C10 84.2(2)
O1 C3 C5 C6 8.1(2)
C2 C3 C5 C6 -94.4(2)
C10 C5 C6 C7 0.5(3)
C3 C5 C6 C7 179.03(16)
C5 C6 C7 C8 -1.6(3)
C6 C7 C8 C9 1.0(3)
C6 C7 C8 N1 -177.45(15)
O4 N1 C8 C7 171.01(16)
O3 N1 C8 C7 -8.4(2)
O4 N1 C8 C9 -7.5(2)
O3 N1 C8 C9 173.12(16)
C7 C8 C9 C10 0.7(3)
N1 C8 C9 C10 179.21(16)
C8 C9 C10 C5 -1.9(3)
C6 C5 C10 C9 1.3(3)
C3 C5 C10 C9 -177.31(16)
C1 C2 C11 C16 -6.8(3)
C4 C2 C11 C16 124.0(2)
C3 C2 C11 C16 -101.3(2)
C1 C2 C11 C12 172.78(17)
C4 C2 C11 C12 -56.4(2)
C3 C2 C11 C12 78.4(2)
C16 C11 C12 C13 0.3(3)
C2 C11 C12 C13 -179.35(18)
C11 C12 C13 C14 -0.2(3)
C12 C13 C14 C15 0.2(3)
C13 C14 C15 C16 -0.4(3)
C12 C11 C16 C15 -0.5(3)
C2 C11 C16 C15 179.17(19)
C14 C15 C16 C11 0.5(4)
