#------------------------------------------------------------------------------
#$Date: 2016-03-21 05:34:46 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178485 $
#$URL: svn://www.crystallography.net/cod/cif/4/03/06/4030643.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_4030643
loop_
_publ_author_name
'Xu, Feng'
'Peng, Lifen'
'Shinohara, Kenta'
'Morita, Takamoto'
'Yoshida, Suguru'
'Hosoya, Takamitsu'
'Orita, Akihiro'
'Otera, Junzo'
_publ_section_title
;
 Substituted 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctenes: syntheses,
 properties, and DFT studies of substituted Sondheimer-Wong diynes.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11592
_journal_page_last               11608
_journal_paper_doi               10.1021/jo502248p
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C13 H10 N2 O'
_chemical_formula_sum            'C13 H10 N2 O'
_chemical_formula_weight         210.23
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.663(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3806(8)
_cell_length_b                   16.057(2)
_cell_length_c                   9.1541(10)
_cell_measurement_reflns_used    14563
_cell_measurement_temperature    122(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.54
_cell_volume                     1021.6(2)
_computing_cell_refinement       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_collection       'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_data_reduction        'APEX2 v.2013.6-2, Bruker/Nonius'
_computing_molecular_graphics    'ORTEP-II (Johnson, 1976)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_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  0.1096
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14563
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2252
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0475
_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)+(0.0453P)²+0.3068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1118
_reflns_number_gt                1487
_reflns_number_total             2252
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo502248p_si_003.cif
_cod_data_source_block           mo_d8v662_0m
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4030643
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
O1 O 0.52597(17) 0.53286(9) 0.15462(14) 0.0235(4) Uani 1 1 d .
H1 H 0.6277 0.5208 0.1374 0.035 Uiso 1 1 calc R
N1 N 1.1305(2) 0.53932(12) 0.87613(17) 0.0269(4) Uani 1 1 d .
N2 N 0.9034(2) 0.68945(11) 1.15936(19) 0.0251(4) Uani 1 1 d .
C1 C 0.5705(2) 0.56394(12) 0.3005(2) 0.0156(4) Uani 1 1 d .
C2 C 0.7608(2) 0.57592(12) 0.3978(2) 0.0161(4) Uani 1 1 d .
H2 H 0.8646 0.5638 0.3618 0.019 Uiso 1 1 calc R
C3 C 0.7963(2) 0.60528(12) 0.5454(2) 0.0156(4) Uani 1 1 d .
H3 H 0.9257 0.6130 0.6111 0.019 Uiso 1 1 calc R
C4 C 0.6464(2) 0.62427(12) 0.60238(19) 0.0135(4) Uani 1 1 d .
C5 C 0.6832(2) 0.65003(12) 0.7625(2) 0.0148(4) Uani 1 1 d .
C6 C 0.8492(2) 0.63276(12) 0.8832(2) 0.0154(4) Uani 1 1 d .
C7 C 1.0034(3) 0.58115(13) 0.8754(2) 0.0191(4) Uani 1 1 d .
C8 C 0.4200(2) 0.58674(12) 0.3510(2) 0.0155(4) Uani 1 1 d .
H8 H 0.2911 0.5810 0.2828 0.019 Uiso 1 1 calc R
C9 C 0.4546(2) 0.61770(12) 0.4992(2) 0.0137(4) Uani 1 1 d .
C10 C 0.2912(2) 0.64692(13) 0.5507(2) 0.0181(4) Uani 1 1 d .
H10A H 0.2492 0.6009 0.6039 0.022 Uiso 1 1 calc R
H10B H 0.1806 0.6635 0.4591 0.022 Uiso 1 1 calc R
C11 C 0.3566(3) 0.72072(13) 0.6606(2) 0.0215(5) Uani 1 1 d .
H11A H 0.3947 0.7673 0.6063 0.026 Uiso 1 1 calc R
H11B H 0.2491 0.7399 0.6938 0.026 Uiso 1 1 calc R
C12 C 0.5263(3) 0.69552(13) 0.8019(2) 0.0190(4) Uani 1 1 d .
H12A H 0.5818 0.7462 0.8620 0.023 Uiso 1 1 calc R
H12B H 0.4790 0.6593 0.8690 0.023 Uiso 1 1 calc R
C13 C 0.8769(2) 0.66427(13) 1.0363(2) 0.0172(4) 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
C1 O1 H1 109.5
O1 C1 C8 117.94(16)
O1 C1 C2 122.33(16)
C8 C1 C2 119.70(16)
C3 C2 C1 119.49(16)
C3 C2 H2 120.3
C1 C2 H2 120.3
C2 C3 C4 121.79(16)
C2 C3 H3 119.1
C4 C3 H3 119.1
C3 C4 C9 118.11(15)
C3 C4 C5 122.05(16)
C9 C4 C5 119.84(15)
C6 C5 C4 124.41(16)
C6 C5 C12 116.93(16)
C4 C5 C12 118.60(16)
C5 C6 C7 125.90(16)
C5 C6 C13 120.55(16)
C7 C6 C13 113.49(16)
N1 C7 C6 176.95(19)
C9 C8 C1 121.09(16)
C9 C8 H8 119.5
C1 C8 H8 119.5
C8 C9 C4 119.54(15)
C8 C9 C10 120.91(16)
C4 C9 C10 119.53(15)
C9 C10 C11 109.80(15)
C9 C10 H10A 109.7
C11 C10 H10A 109.7
C9 C10 H10B 109.7
C11 C10 H10B 109.7
H10A C10 H10B 108.2
C12 C11 C10 109.99(16)
C12 C11 H11A 109.7
C10 C11 H11A 109.7
C12 C11 H11B 109.7
C10 C11 H11B 109.7
H11A C11 H11B 108.2
C5 C12 C11 113.74(15)
C5 C12 H12A 108.8
C11 C12 H12A 108.8
C5 C12 H12B 108.8
C11 C12 H12B 108.8
H12A C12 H12B 107.7
N2 C13 C6 178.44(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.358(2)
O1 H1 0.8400
N1 C7 1.152(2)
N2 C13 1.150(2)
C1 C8 1.388(2)
C1 C2 1.401(2)
C2 C3 1.371(2)
C2 H2 0.9500
C3 C4 1.406(2)
C3 H3 0.9500
C4 C9 1.417(2)
C4 C5 1.458(2)
C5 C6 1.374(2)
C5 C12 1.512(2)
C6 C7 1.429(3)
C6 C13 1.438(2)
C8 C9 1.386(2)
C8 H8 0.9500
C9 C10 1.509(2)
C10 C11 1.524(3)
C10 H10A 0.9900
C10 H10B 0.9900
C11 C12 1.522(3)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9900
C12 H12B 0.9900
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
O1 C1 C2 C3 -178.12(18)
C8 C1 C2 C3 4.0(3)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C9 -4.2(3)
C2 C3 C4 C5 175.69(18)
C3 C4 C5 C6 -22.6(3)
C9 C4 C5 C6 157.37(18)
C3 C4 C5 C12 160.31(18)
C9 C4 C5 C12 -19.8(3)
C4 C5 C6 C7 -6.1(3)
C12 C5 C6 C7 171.08(18)
C4 C5 C6 C13 176.89(17)
C12 C5 C6 C13 -5.9(3)
C5 C6 C7 N1 -162(4)
C13 C6 C7 N1 15(4)
O1 C1 C8 C9 179.00(17)
C2 C1 C8 C9 -3.0(3)
C1 C8 C9 C4 -1.6(3)
C1 C8 C9 C10 176.55(17)
C3 C4 C9 C8 5.2(3)
C5 C4 C9 C8 -174.77(18)
C3 C4 C9 C10 -173.04(17)
C5 C4 C9 C10 7.0(3)
C8 C9 C10 C11 -145.39(18)
C4 C9 C10 C11 32.8(2)
C9 C10 C11 C12 -59.5(2)
C6 C5 C12 C11 173.63(17)
C4 C5 C12 C11 -9.0(3)
C10 C11 C12 C5 48.2(2)
C5 C6 C13 N2 -152(8)
C7 C6 C13 N2 30(8)
