#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/36/4023681.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_4023681
loop_
_publ_author_name
'Bradley O. Ashburn'
'Rich G. Carter'
'Lev N. Zakharov'
_publ_section_title
;
 Diels-Alder Approach to Biaryls: Elucidation of Competing Tandem
 [2+2] Cycloaddition/[1,3] Sigmatropic Shift Pathway
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7305
_journal_page_last               7309
_journal_paper_doi               10.1021/jo801245a
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C16 H14 Cl N O4'
_chemical_formula_weight         319.73
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                112.1860(10)
_cell_angle_beta                 108.3350(10)
_cell_angle_gamma                98.7220(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7746(6)
_cell_length_b                   10.5790(8)
_cell_length_c                   10.8866(8)
_cell_measurement_reflns_used    4137
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.10
_cell_measurement_theta_min      2.19
_cell_volume                     748.84(10)
_computing_cell_refinement       'Bruker SMART'
_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      173(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector Bruker Apex'
_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  0.0137
_diffrn_reflns_av_sigmaI/netI    0.0164
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8450
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.19
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.9628
_exptl_absorpt_correction_T_min  0.9130
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3247
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0342
_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)+(0.0490P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0958
_reflns_number_gt                2936
_reflns_number_total             3247
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801245a_si_004.cif
_cod_data_source_block           rc26
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4023681
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 1.17231(6) 0.09970(5) 0.81269(5) 0.04674(14) Uani 1 1 d . . .
N1 N 0.75450(16) 0.34445(13) 0.56462(12) 0.0297(3) Uani 1 1 d . . .
O1 O 0.55585(16) 0.40737(12) 1.14384(12) 0.0401(3) Uani 1 1 d . . .
O2 O 0.66209(16) 0.25498(12) 1.22138(12) 0.0401(3) Uani 1 1 d . . .
O3 O 0.59905(14) 0.26572(12) 0.53239(11) 0.0378(3) Uani 1 1 d . . .
O4 O 0.78535(17) 0.46715(12) 0.57934(13) 0.0456(3) Uani 1 1 d . . .
C1 C 0.7424(2) 0.36065(14) 0.96425(14) 0.0289(3) Uani 1 1 d . . .
C2 C 0.83823(19) 0.34250(14) 0.86517(14) 0.0280(3) Uani 1 1 d . . .
C3 C 0.83471(18) 0.21828(14) 0.76597(13) 0.0254(3) Uani 1 1 d . . .
C4 C 0.70936(19) 0.07323(14) 0.71659(14) 0.0284(3) Uani 1 1 d . . .
C5 C 0.6696(2) 0.00182(15) 0.78736(15) 0.0312(3) Uani 1 1 d . . .
C6 C 0.7499(2) 0.03788(16) 0.94472(16) 0.0338(3) Uani 1 1 d . . .
C7 C 0.8721(2) 0.19233(16) 1.05037(15) 0.0313(3) Uani 1 1 d . . .
C8 C 0.75751(18) 0.29448(14) 1.04847(13) 0.0271(3) Uani 1 1 d . . .
C9 C 0.65560(19) 0.31587(14) 1.14689(14) 0.0283(3) Uani 1 1 d . . .
C10 C 0.4490(3) 0.4251(2) 1.2333(2) 0.0450(4) Uani 1 1 d . . .
C11 C 0.95110(18) 0.22486(14) 0.68017(13) 0.0258(3) Uani 1 1 d . . .
C12 C 1.1085(2) 0.17394(15) 0.69411(15) 0.0317(3) Uani 1 1 d . . .
C13 C 1.2205(2) 0.18349(18) 0.61863(17) 0.0378(3) Uani 1 1 d . . .
C14 C 1.1781(2) 0.24599(18) 0.52656(17) 0.0380(3) Uani 1 1 d . . .
C15 C 1.0269(2) 0.30117(16) 0.51122(15) 0.0326(3) Uani 1 1 d . . .
C16 C 0.91761(18) 0.28809(14) 0.58715(14) 0.0264(3) Uani 1 1 d . . .
H1 H 0.677(2) 0.4271(18) 0.9739(18) 0.034(4) Uiso 1 1 d . . .
H2 H 0.912(2) 0.4287(18) 0.8719(17) 0.033(4) Uiso 1 1 d . . .
H4 H 0.650(2) 0.0230(18) 0.6136(19) 0.037(4) Uiso 1 1 d . . .
H5 H 0.583(2) -0.0949(19) 0.7293(18) 0.038(4) Uiso 1 1 d . . .
H6A H 0.643(3) 0.0142(18) 0.9725(19) 0.041(4) Uiso 1 1 d . . .
H6B H 0.823(3) -0.0246(19) 0.9579(19) 0.043(5) Uiso 1 1 d . . .
H7A H 0.976(2) 0.2175(17) 1.0256(17) 0.033(4) Uiso 1 1 d . . .
H7B H 0.924(2) 0.2009(17) 1.1460(19) 0.039(4) Uiso 1 1 d . . .
H10A H 0.405(3) 0.502(3) 1.233(2) 0.069(6) Uiso 1 1 d . . .
H10B H 0.345(3) 0.341(3) 1.191(3) 0.072(7) Uiso 1 1 d . . .
H10C H 0.534(3) 0.449(2) 1.336(2) 0.054(5) Uiso 1 1 d . . .
H13 H 1.326(3) 0.1476(19) 0.6309(19) 0.044(5) Uiso 1 1 d . . .
H14 H 1.250(3) 0.2539(19) 0.475(2) 0.044(5) Uiso 1 1 d . . .
H15 H 0.993(2) 0.3437(18) 0.4520(18) 0.036(4) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 N1 O4 124.79(12) . . ?
O3 N1 C16 117.91(11) . . ?
O4 N1 C16 117.30(11) . . ?
C9 O1 C10 114.96(12) . . ?
C8 C1 C2 123.40(13) . . ?
C8 C1 H1 118.9(10) . . ?
C2 C1 H1 117.5(10) . . ?
C3 C2 C1 126.77(12) . . ?
C3 C2 H2 116.3(9) . . ?
C1 C2 H2 116.9(10) . . ?
C2 C3 C4 127.12(12) . . ?
C2 C3 C11 117.77(11) . . ?
C4 C3 C11 114.63(11) . . ?
C5 C4 C3 132.79(13) . . ?
C5 C4 H4 116.2(10) . . ?
C3 C4 H4 111.0(10) . . ?
C4 C5 C6 131.54(13) . . ?
C4 C5 H5 117.2(10) . . ?
C6 C5 H5 111.0(10) . . ?
C5 C6 C7 116.56(12) . . ?
C5 C6 H6A 108.8(10) . . ?
C7 C6 H6A 108.2(10) . . ?
C5 C6 H6B 108.4(11) . . ?
C7 C6 H6B 108.8(11) . . ?
H6A C6 H6B 105.5(15) . . ?
C8 C7 C6 111.34(12) . . ?
C8 C7 H7A 109.5(10) . . ?
C6 C7 H7A 109.7(10) . . ?
C8 C7 H7B 109.1(10) . . ?
C6 C7 H7B 109.2(10) . . ?
H7A C7 H7B 107.9(14) . . ?
C1 C8 C9 121.27(12) . . ?
C1 C8 C7 123.74(12) . . ?
C9 C8 C7 114.98(11) . . ?
O2 C9 O1 123.16(12) . . ?
O2 C9 C8 122.97(12) . . ?
O1 C9 C8 113.86(11) . . ?
O1 C10 H10A 105.3(14) . . ?
O1 C10 H10B 109.5(14) . . ?
H10A C10 H10B 110(2) . . ?
O1 C10 H10C 110.5(11) . . ?
H10A C10 H10C 109.3(18) . . ?
H10B C10 H10C 111.8(18) . . ?
C16 C11 C12 114.90(11) . . ?
C16 C11 C3 123.08(11) . . ?
C12 C11 C3 121.94(12) . . ?
C13 C12 C11 122.39(13) . . ?
C13 C12 Cl1 117.98(11) . . ?
C11 C12 Cl1 119.61(10) . . ?
C14 C13 C12 119.79(13) . . ?
C14 C13 H13 120.3(11) . . ?
C12 C13 H13 119.9(11) . . ?
C15 C14 C13 120.31(13) . . ?
C15 C14 H14 118.2(11) . . ?
C13 C14 H14 121.5(11) . . ?
C14 C15 C16 118.08(13) . . ?
C14 C15 H15 124.0(10) . . ?
C16 C15 H15 117.9(11) . . ?
C15 C16 C11 124.50(12) . . ?
C15 C16 N1 116.44(12) . . ?
C11 C16 N1 119.05(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C12 1.7350(14) . ?
N1 O3 1.2184(15) . ?
N1 O4 1.2216(16) . ?
N1 C16 1.4724(17) . ?
O1 C9 1.3323(17) . ?
O1 C10 1.4466(17) . ?
O2 C9 1.2058(16) . ?
C1 C8 1.3366(19) . ?
C1 C2 1.4656(17) . ?
C1 H1 0.922(17) . ?
C2 C3 1.3389(19) . ?
C2 H2 0.964(17) . ?
C3 C4 1.4789(18) . ?
C3 C11 1.5026(16) . ?
C4 C5 1.3335(19) . ?
C4 H4 0.950(17) . ?
C5 C6 1.494(2) . ?
C5 H5 0.968(17) . ?
C6 C7 1.522(2) . ?
C6 H6A 1.002(18) . ?
C6 H6B 0.958(19) . ?
C7 C8 1.5030(19) . ?
C7 H7A 0.960(17) . ?
C7 H7B 0.953(18) . ?
C8 C9 1.4940(17) . ?
C10 H10A 0.93(2) . ?
C10 H10B 0.95(2) . ?
C10 H10C 1.01(2) . ?
C11 C16 1.3925(18) . ?
C11 C12 1.3986(19) . ?
C12 C13 1.3890(19) . ?
C13 C14 1.382(2) . ?
C13 H13 0.949(18) . ?
C14 C15 1.381(2) . ?
C14 H14 0.923(19) . ?
C15 C16 1.3848(18) . ?
C15 H15 0.915(18) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C3 50.9(2) . . . . ?
C1 C2 C3 C4 11.1(2) . . . . ?
C1 C2 C3 C11 -177.31(13) . . . . ?
C2 C3 C4 C5 -51.4(2) . . . . ?
C11 C3 C4 C5 136.79(16) . . . . ?
C3 C4 C5 C6 -5.7(3) . . . . ?
C4 C5 C6 C7 13.1(2) . . . . ?
C5 C6 C7 C8 64.44(16) . . . . ?
C2 C1 C8 C9 -179.54(12) . . . . ?
C2 C1 C8 C7 -0.8(2) . . . . ?
C6 C7 C8 C1 -92.64(16) . . . . ?
C6 C7 C8 C9 86.14(14) . . . . ?
C10 O1 C9 O2 -2.1(2) . . . . ?
C10 O1 C9 C8 177.37(13) . . . . ?
C1 C8 C9 O2 177.99(13) . . . . ?
C7 C8 C9 O2 -0.83(19) . . . . ?
C1 C8 C9 O1 -1.49(19) . . . . ?
C7 C8 C9 O1 179.69(12) . . . . ?
C2 C3 C11 C16 -62.96(17) . . . . ?
C4 C3 C11 C16 109.63(14) . . . . ?
C2 C3 C11 C12 113.62(15) . . . . ?
C4 C3 C11 C12 -73.79(16) . . . . ?
C16 C11 C12 C13 -1.2(2) . . . . ?
C3 C11 C12 C13 -177.99(13) . . . . ?
C16 C11 C12 Cl1 177.23(10) . . . . ?
C3 C11 C12 Cl1 0.40(18) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
Cl1 C12 C13 C14 -177.99(12) . . . . ?
C12 C13 C14 C15 1.1(2) . . . . ?
C13 C14 C15 C16 -1.8(2) . . . . ?
C14 C15 C16 C11 1.0(2) . . . . ?
C14 C15 C16 N1 -178.27(13) . . . . ?
C12 C11 C16 C15 0.4(2) . . . . ?
C3 C11 C16 C15 177.22(13) . . . . ?
C12 C11 C16 N1 179.71(12) . . . . ?
C3 C11 C16 N1 -3.50(19) . . . . ?
O3 N1 C16 C15 128.44(13) . . . . ?
O4 N1 C16 C15 -51.35(17) . . . . ?
O3 N1 C16 C11 -50.90(16) . . . . ?
O4 N1 C16 C11 129.30(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26597947
