#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:43:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180312 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/26/7152665.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_7152665
loop_
_publ_author_name
'McIntosh, Melissa L.'
'Naffziger, Michael R.'
'Ashburn, Bradley O.'
'Zakharov, Lev N.'
'Carter, Rich G.'
_publ_section_title
;
 Highly regioselective nitrile oxide dipolar cycloadditions with
 ortho-nitrophenyl alkynes.
;
_journal_issue                   46
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9204
_journal_page_last               9213
_journal_paper_doi               10.1039/c2ob26267c
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C16 H14 N2 O4'
_chemical_formula_weight         298.29
_chemical_name_systematic
;

?

;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.238(4)
_cell_length_b                   8.006(3)
_cell_length_c                   28.867(10)
_cell_measurement_reflns_used    1249
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      19.34
_cell_measurement_theta_min      2.18
_cell_volume                     2828.3(17)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_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      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Apex 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  0.0889
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            18841
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.41
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.9650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.611
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2501
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.0641
_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)+(0.0944P)²+1.3864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1590
_refine_ls_wR_factor_ref         0.1919
_reflns_number_gt                1531
_reflns_number_total             2501
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob26267c.txt
_cod_data_source_block           rc71a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7152665
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O1 O 0.0182(2) 1.0694(4) 0.44778(10) 0.0542(8) Uani 1 1 d
O2 O -0.0889(2) 0.9936(4) 0.38830(10) 0.0575(9) Uani 1 1 d
O3 O 0.1454(2) 0.7649(3) 0.19905(8) 0.0427(7) Uani 1 1 d
O4 O 0.6365(2) 1.0302(3) 0.42133(9) 0.0477(8) Uani 1 1 d
N1 N 0.1272(3) 1.0850(4) 0.45696(13) 0.0497(10) Uani 1 1 d
N2 N 0.0043(3) 1.0152(4) 0.40137(12) 0.0452(9) Uani 1 1 d
C1 C 0.1779(3) 1.0420(4) 0.41696(13) 0.0352(9) Uani 1 1 d
C2 C 0.1024(3) 0.9984(4) 0.38171(13) 0.0352(9) Uani 1 1 d
C3 C 0.1139(3) 0.9432(4) 0.33317(13) 0.0351(9) Uani 1 1 d
C4 C 0.1899(3) 1.0164(5) 0.30376(13) 0.0361(9) Uani 1 1 d
C5 C 0.2026(3) 0.9610(5) 0.25864(14) 0.0370(9) Uani 1 1 d
C6 C 0.1384(3) 0.8320(5) 0.24234(12) 0.0319(8) Uani 1 1 d
C7 C 0.0595(3) 0.7601(5) 0.27143(14) 0.0391(10) Uani 1 1 d
C8 C 0.0480(3) 0.8143(5) 0.31590(14) 0.0375(9) Uani 1 1 d
C9 C 0.2333(4) 0.8226(7) 0.17019(16) 0.0470(11) Uani 1 1 d
C10 C 0.2977(3) 1.0437(4) 0.41693(12) 0.0334(9) Uani 1 1 d
C11 C 0.3586(3) 0.9407(5) 0.38770(14) 0.0349(9) Uani 1 1 d
C12 C 0.4715(3) 0.9376(5) 0.39032(13) 0.0372(9) Uani 1 1 d
C13 C 0.5260(3) 1.0402(4) 0.42178(12) 0.0354(9) Uani 1 1 d
C14 C 0.4668(3) 1.1441(5) 0.45107(14) 0.0383(9) Uani 1 1 d
C15 C 0.3538(3) 1.1448(5) 0.44824(13) 0.0367(9) Uani 1 1 d
C16 C 0.6956(4) 1.1370(6) 0.45220(16) 0.0467(11) Uani 1 1 d
H4 H 0.232(3) 1.108(5) 0.3161(12) 0.038(10) Uiso 1 1 d
H5 H 0.253(3) 1.012(4) 0.2388(12) 0.041(10) Uiso 1 1 d
H7 H 0.020(3) 0.673(4) 0.2601(10) 0.023(9) Uiso 1 1 d
H8 H -0.001(3) 0.758(5) 0.3364(13) 0.049(11) Uiso 1 1 d
H9A H 0.314(4) 0.809(6) 0.1864(15) 0.082(15) Uiso 1 1 d
H9B H 0.222(3) 0.940(6) 0.1633(13) 0.055(12) Uiso 1 1 d
H9C H 0.227(3) 0.758(5) 0.1443(14) 0.048(12) Uiso 1 1 d
H11 H 0.328(3) 0.873(5) 0.3663(12) 0.039(11) Uiso 1 1 d
H12 H 0.516(3) 0.866(5) 0.3694(14) 0.057(12) Uiso 1 1 d
H14 H 0.500(3) 1.217(5) 0.4741(13) 0.046(11) Uiso 1 1 d
H15 H 0.315(3) 1.216(5) 0.4701(12) 0.044(11) Uiso 1 1 d
H16A H 0.767(5) 1.100(6) 0.4463(17) 0.086(17) Uiso 1 1 d
H16B H 0.687(3) 1.254(5) 0.4447(12) 0.039(10) Uiso 1 1 d
H16C H 0.678(3) 1.112(4) 0.4849(13) 0.036(10) 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
N1 O1 N2 109.1(3)
C6 O3 C9 116.9(3)
C13 O4 C16 117.6(3)
C1 N1 O1 105.0(3)
O2 N2 C2 134.3(4)
O2 N2 O1 116.7(3)
C2 N2 O1 109.0(3)
N1 C1 C2 112.1(3)
N1 C1 C10 117.1(3)
C2 C1 C10 130.8(3)
N2 C2 C1 104.8(3)
N2 C2 C3 121.3(4)
C1 C2 C3 133.8(3)
C4 C3 C8 118.6(4)
C4 C3 C2 121.2(3)
C8 C3 C2 120.2(3)
C5 C4 C3 121.0(4)
C5 C4 H4 122(2)
C3 C4 H4 117(2)
C6 C5 C4 119.8(4)
C6 C5 H5 120(2)
C4 C5 H5 121(2)
O3 C6 C5 124.9(3)
O3 C6 C7 115.5(3)
C5 C6 C7 119.7(4)
C8 C7 C6 120.3(4)
C8 C7 H7 122(2)
C6 C7 H7 118(2)
C7 C8 C3 120.7(4)
C7 C8 H8 120(2)
C3 C8 H8 119(2)
O3 C9 H9A 113(2)
O3 C9 H9B 109(2)
H9A C9 H9B 108(4)
O3 C9 H9C 103(3)
H9A C9 H9C 112(3)
H9B C9 H9C 112(3)
C15 C10 C11 118.1(3)
C15 C10 C1 119.8(3)
C11 C10 C1 122.0(3)
C12 C11 C10 120.7(4)
C12 C11 H11 116(2)
C10 C11 H11 123(2)
C11 C12 C13 120.2(4)
C11 C12 H12 122(2)
C13 C12 H12 118(2)
O4 C13 C14 124.2(3)
O4 C13 C12 115.9(3)
C14 C13 C12 119.9(4)
C15 C14 C13 119.2(4)
C15 C14 H14 117(2)
C13 C14 H14 124(2)
C14 C15 C10 121.8(4)
C14 C15 H15 117(2)
C10 C15 H15 121(2)
O4 C16 H16A 100(3)
O4 C16 H16B 112(2)
H16A C16 H16B 112(4)
O4 C16 H16C 111(2)
H16A C16 H16C 108(4)
H16B C16 H16C 113(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.366(4)
O1 N2 1.418(4)
O2 N2 1.214(4)
O3 C6 1.363(4)
O3 C9 1.437(5)
O4 C13 1.355(4)
O4 C16 1.431(5)
N1 C1 1.355(5)
N2 C2 1.334(5)
C1 C2 1.418(5)
C1 C10 1.467(5)
C2 C3 1.476(5)
C3 C4 1.389(5)
C3 C8 1.401(5)
C4 C5 1.385(5)
C4 H4 0.97(4)
C5 C6 1.380(5)
C5 H5 0.93(4)
C6 C7 1.403(5)
C7 C8 1.362(5)
C7 H7 0.91(3)
C8 H8 0.96(4)
C9 H9A 1.10(5)
C9 H9B 0.98(4)
C9 H9C 0.92(4)
C10 C15 1.394(5)
C10 C11 1.395(5)
C11 C12 1.384(5)
C11 H11 0.91(4)
C12 C13 1.394(5)
C12 H12 1.00(4)
C13 C14 1.390(5)
C14 C15 1.385(5)
C14 H14 0.97(4)
C15 H15 0.97(4)
C16 H16A 0.94(6)
C16 H16B 0.97(4)
C16 H16C 0.99(4)
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
N2 O1 N1 C1 0.3(4)
N1 O1 N2 O2 179.1(3)
N1 O1 N2 C2 -0.5(4)
O1 N1 C1 C2 0.0(4)
O1 N1 C1 C10 -178.7(3)
O2 N2 C2 C1 -179.0(4)
O1 N2 C2 C1 0.5(4)
O2 N2 C2 C3 0.5(6)
O1 N2 C2 C3 179.9(3)
N1 C1 C2 N2 -0.3(4)
C10 C1 C2 N2 178.1(4)
N1 C1 C2 C3 -179.7(4)
C10 C1 C2 C3 -1.2(7)
N2 C2 C3 C4 138.9(4)
C1 C2 C3 C4 -41.8(6)
N2 C2 C3 C8 -41.4(5)
C1 C2 C3 C8 137.9(4)
C8 C3 C4 C5 -1.6(5)
C2 C3 C4 C5 178.2(3)
C3 C4 C5 C6 0.6(5)
C9 O3 C6 C5 6.3(5)
C9 O3 C6 C7 -173.1(3)
C4 C5 C6 O3 -178.4(3)
C4 C5 C6 C7 1.0(5)
O3 C6 C7 C8 178.0(3)
C5 C6 C7 C8 -1.5(5)
C6 C7 C8 C3 0.4(6)
C4 C3 C8 C7 1.1(6)
C2 C3 C8 C7 -178.7(3)
N1 C1 C10 C15 -24.7(5)
C2 C1 C10 C15 156.9(4)
N1 C1 C10 C11 152.3(3)
C2 C1 C10 C11 -26.1(6)
C15 C10 C11 C12 1.0(5)
C1 C10 C11 C12 -176.1(3)
C10 C11 C12 C13 -1.3(5)
C16 O4 C13 C14 -1.7(5)
C16 O4 C13 C12 178.3(3)
C11 C12 C13 O4 -179.0(3)
C11 C12 C13 C14 1.0(5)
O4 C13 C14 C15 179.6(3)
C12 C13 C14 C15 -0.5(5)
C13 C14 C15 C10 0.2(5)
C11 C10 C15 C14 -0.5(5)
C1 C10 C15 C14 176.7(3)
