#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:42:19 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178439 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/60/4026071.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_4026071
loop_
_publ_author_name
'Roman A. Valiulin'
'Teresa M. Arisco'
'Andrei G. Kutateladze'
_publ_contact_author_address
;Department of Chemistry and Biochemistry
University of Denver
FW Olin Hall, 202
2190 E. Iliff Ave
Denver, CO 80208
;
_publ_contact_author_email       akutatel.edu
_publ_contact_author_fax         303-871-2254
_publ_contact_author_name        'Andrei Kutateladze'
_publ_contact_author_phone       303-871-2995
_publ_section_title
;
 Double-Tandem [4π+2π].[2π+2π].[4π+2π].[2π+2π] Synthetic Sequence
 with Photoprotolytic Oxametathesis and Photoepoxidation in the Chromone
 Series
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1319
_journal_page_last               1332
_journal_paper_doi               10.1021/jo102221q
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C16 H13 N O2'
_chemical_formula_sum            'C16 H13 N O2'
_chemical_formula_weight         251.28
_chemical_name_common            none
_chemical_name_systematic
;
endo-4,5-Benzo-7-cyano-3-oxatricyclo[6.2.2.0^2,7^]
dodec-9-ene-6-one
;
_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           SHELXL-97
_cell_angle_alpha                88.7440(10)
_cell_angle_beta                 81.7220(10)
_cell_angle_gamma                65.2350(10)
_cell_formula_units_Z            2
_cell_length_a                   6.66960(10)
_cell_length_b                   7.6973(2)
_cell_length_c                   12.7164(3)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      48.07
_cell_measurement_theta_min      2.92
_cell_volume                     586.08(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Bruker D8 APEX II Diffractometer'
_diffrn_measurement_method       'φ and ω 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  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0188
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            38728
_diffrn_reflns_theta_full        48.17
_diffrn_reflns_theta_max         48.17
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       prism
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.783
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         10818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.832
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0464
_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)+(0.1265P)²+0.1451P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1722
_reflns_number_gt                8904
_reflns_number_total             10818
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102221q_si_002.cif
_cod_data_source_block           cn_chromone_exo_0m
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4026071
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
O1 O -0.13858(8) 0.29156(9) 0.62754(3) 0.02397(9) Uani 1 1 d .
O2 O 0.25463(7) 0.51041(7) 0.74411(4) 0.02072(8) Uani 1 1 d .
C100 C -0.19903(8) 0.34643(7) 0.73914(4) 0.01564(7) Uani 1 1 d .
H1 H -0.3506 0.4491 0.7498 0.019 Uiso 1 1 calc R
C7 C 0.17466(11) 0.07671(9) 0.82994(5) 0.02540(11) Uani 1 1 d .
H7 H 0.3262 -0.0001 0.8281 0.030 Uiso 1 1 calc R
C13 C 0.44444(11) 0.23918(10) 0.43786(5) 0.02383(10) Uani 1 1 d .
H13 H 0.5732 0.2276 0.3933 0.029 Uiso 1 1 calc R
C10 C -0.29191(12) 0.23570(10) 0.91600(5) 0.02382(10) Uani 1 1 d .
H10A H -0.4351 0.3460 0.9221 0.029 Uiso 1 1 calc R
H10B H -0.3135 0.1330 0.9543 0.029 Uiso 1 1 calc R
C6 C 0.29656(12) 0.17505(9) 0.40267(4) 0.02342(10) Uani 1 1 d .
H6 H 0.3286 0.1201 0.3344 0.028 Uiso 1 1 calc R
C8 C 0.03037(11) 0.01850(8) 0.78789(5) 0.02206(9) Uani 1 1 d .
H8 H 0.0744 -0.1024 0.7566 0.026 Uiso 1 1 calc R
C5 C 0.10409(11) 0.19199(8) 0.46751(4) 0.02045(9) Uani 1 1 d .
H5 H 0.0070 0.1493 0.4430 0.025 Uiso 1 1 calc R
C11 C -0.13210(11) 0.28552(8) 0.96393(4) 0.02003(8) Uani 1 1 d .
H11A H -0.0721 0.1962 1.0184 0.024 Uiso 1 1 calc R
H11B H -0.2092 0.4130 0.9974 0.024 Uiso 1 1 calc R
N1 N -0.28463(9) 0.76250(8) 0.87664(4) 0.02211(8) Uani 1 1 d .
C14 C 0.39719(9) 0.31979(8) 0.53938(4) 0.01845(8) Uani 1 1 d .
H14 H 0.4948 0.3625 0.5632 0.022 Uiso 1 1 calc R
C12 C 0.05908(9) 0.27868(8) 0.87905(4) 0.01823(8) Uani 1 1 d .
H12 H 0.1638 0.3142 0.9099 0.022 Uiso 1 1 calc R
C9 C -0.20542(9) 0.17253(8) 0.79851(4) 0.01803(8) Uani 1 1 d .
H9 H -0.3028 0.1261 0.7690 0.022 Uiso 1 1 calc R
C2 C -0.17871(8) 0.61112(7) 0.83773(4) 0.01656(7) Uani 1 1 d .
C4 C 0.05597(9) 0.27408(7) 0.57052(4) 0.01548(7) Uani 1 1 d .
C16 C 0.14995(7) 0.42948(7) 0.71259(4) 0.01395(6) Uani 1 1 d .
C3 C -0.04502(7) 0.41826(7) 0.78913(3) 0.01369(6) Uani 1 1 d .
C15 C 0.20248(8) 0.33785(6) 0.60703(3) 0.01372(6) Uani 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
C4 O1 C100 123.13(4)
O1 C100 C9 107.22(4)
O1 C100 C3 116.54(4)
C9 C100 C3 109.25(4)
O1 C100 H1 107.8
C9 C100 H1 107.8
C3 C100 H1 107.8
C8 C7 C12 112.95(5)
C8 C7 H7 123.5
C12 C7 H7 123.5
C14 C13 C6 119.35(5)
C14 C13 H13 120.3
C6 C13 H13 120.3
C11 C10 C9 110.74(5)
C11 C10 H10A 109.5
C9 C10 H10A 109.5
C11 C10 H10B 109.5
C9 C10 H10B 109.5
H10A C10 H10B 108.1
C5 C6 C13 121.16(5)
C5 C6 H6 119.4
C13 C6 H6 119.4
C7 C8 C9 112.82(5)
C7 C8 H8 123.6
C9 C8 H8 123.6
C6 C5 C4 119.49(5)
C6 C5 H5 120.3
C4 C5 H5 120.3
C10 C11 C12 110.63(4)
C10 C11 H11A 109.5
C12 C11 H11A 109.5
C10 C11 H11B 109.5
C12 C11 H11B 109.5
H11A C11 H11B 108.1
C13 C14 C15 120.50(5)
C13 C14 H14 119.7
C15 C14 H14 119.7
C7 C12 C11 107.40(5)
C7 C12 C3 107.81(4)
C11 C12 C3 108.21(4)
C7 C12 H12 111.1
C11 C12 H12 111.1
C3 C12 H12 111.1
C8 C9 C10 109.41(5)
C8 C9 C100 107.92(4)
C10 C9 C100 107.53(4)
C8 C9 H9 110.6
C10 C9 H9 110.6
C100 C9 H9 110.6
N1 C2 C3 179.50(6)
O1 C4 C15 123.99(4)
O1 C4 C5 115.93(5)
C15 C4 C5 120.04(5)
O2 C16 C15 123.69(4)
O2 C16 C3 118.61(4)
C15 C16 C3 117.68(4)
C2 C3 C16 106.62(4)
C2 C3 C100 109.56(4)
C16 C3 C100 116.32(4)
C2 C3 C12 108.54(4)
C16 C3 C12 107.25(4)
C100 C3 C12 108.32(4)
C4 C15 C14 119.46(4)
C4 C15 C16 120.42(4)
C14 C15 C16 120.08(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C4 1.3471(7)
O1 C100 1.4400(7)
O2 C16 1.2214(6)
C100 C9 1.5355(7)
C100 C3 1.5635(6)
C100 H1 0.9800
C7 C8 1.3902(10)
C7 C12 1.5170(9)
C7 H7 0.9300
C13 C14 1.3803(8)
C13 C6 1.4004(10)
C13 H13 0.9300
C10 C11 1.4813(9)
C10 C9 1.5331(8)
C10 H10A 0.9700
C10 H10B 0.9700
C6 C5 1.3800(9)
C6 H6 0.9300
C8 C9 1.5102(9)
C8 H8 0.9300
C5 C4 1.4013(7)
C5 H5 0.9300
C11 C12 1.5309(8)
C11 H11A 0.9700
C11 H11B 0.9700
N1 C2 1.1561(7)
C14 C15 1.4064(7)
C14 H14 0.9300
C12 C3 1.5791(7)
C12 H12 0.9800
C9 H9 0.9800
C2 C3 1.4674(7)
C4 C15 1.3977(6)
C16 C15 1.4565(6)
C16 C3 1.5400(6)
