#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:54:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178449 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/70/4027095.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_4027095
loop_
_publ_author_name
'Rafael P. Bula'
'Iris M. Oppel'
'Holger F. Bettinger'
_publ_section_title
;
 Thermal Generation of Pentacenes from Soluble
 6,13-Dihydro-6,13-ethenopentacene Precursors by a
 Diels-Alder-retro-Diels-Alder Sequence with 3,6-Disubstituted Tetrazines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3538
_journal_page_last               3542
_journal_paper_doi               10.1021/jo202450u
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C12 H20 O4'
_chemical_formula_weight         228.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 106.497(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3934(2)
_cell_length_b                   15.6929(4)
_cell_length_c                   10.0693(3)
_cell_measurement_reflns_used    5035
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.87
_cell_volume                     1120.19(6)
_computing_cell_refinement       'CrysAlis RED Oxford diffraction'
_computing_data_collection       'CrysAlis CCD Oxford diffraction'
_computing_data_reduction        'CrysAlis RED Oxford diffraction'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  '562 frames in ω and 10 sec'
_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  0.0302
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9940
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.394
_exptl_crystal_size_min          0.227
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0361
_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)+(0.0558P)²+0.1096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0951
_reflns_number_gt                1733
_reflns_number_total             2194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo202450u_si_001.cif
_cod_data_source_block           p21n
_cod_original_cell_volume        1120.19(5)
_cod_database_code               4027095
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C1 C 0.34088(19) 0.17084(8) 0.38869(13) 0.0120(3) Uani 1 1 d .
H1 H 0.4081 0.2055 0.4714 0.014 Uiso 1 1 calc R
C2 C 0.44605(19) 0.08957(9) 0.38193(14) 0.0145(3) Uani 1 1 d .
H2 H 0.5599 0.0746 0.4496 0.017 Uiso 1 1 calc R
C3 C 0.36684(19) 0.04063(8) 0.27384(14) 0.0137(3) Uani 1 1 d .
H3 H 0.4207 -0.0115 0.2559 0.016 Uiso 1 1 calc R
C4 C 0.18354(18) 0.07516(8) 0.18185(13) 0.0116(3) Uani 1 1 d .
H4 H 0.1287 0.0355 0.1029 0.014 Uiso 1 1 calc R
C5 C 0.22075(18) 0.16383(8) 0.12838(13) 0.0115(3) Uani 1 1 d .
H5 H 0.0960 0.1915 0.0856 0.014 Uiso 1 1 calc R
C6 C 0.33014(19) 0.21957(8) 0.25237(13) 0.0123(3) Uani 1 1 d .
H6 H 0.4619 0.2265 0.2460 0.015 Uiso 1 1 calc R
C7 C 0.13886(19) 0.14791(9) 0.39321(13) 0.0133(3) Uani 1 1 d .
H7 H 0.0619 0.2013 0.3771 0.016 Uiso 1 1 calc R
C8 C 0.04893(18) 0.08505(8) 0.27451(13) 0.0122(3) Uani 1 1 d .
H8 H 0.0396 0.0283 0.3172 0.015 Uiso 1 1 calc R
C51 C 0.32468(19) 0.15790(9) 0.01815(14) 0.0146(3) Uani 1 1 d .
H51A H 0.3535 0.2161 -0.0079 0.018 Uiso 1 1 calc R
H51B H 0.4458 0.1277 0.0570 0.018 Uiso 1 1 calc R
O51 O 0.21624(14) 0.11360(6) -0.10403(9) 0.0157(2) Uani 1 1 d .
H51 H 0.1933 0.0638 -0.0827 0.024 Uiso 1 1 calc R
C61 C 0.2428(2) 0.30806(8) 0.24464(14) 0.0139(3) Uani 1 1 d .
H61A H 0.2493 0.3362 0.1581 0.017 Uiso 1 1 calc R
H61B H 0.1080 0.3023 0.2407 0.017 Uiso 1 1 calc R
O61 O 0.33418(14) 0.36077(6) 0.35961(9) 0.0164(2) Uani 1 1 d .
H61 H 0.4480 0.3671 0.3623 0.025 Uiso 1 1 calc R
C71 C 0.1385(2) 0.11228(9) 0.53324(14) 0.0169(3) Uani 1 1 d .
H71A H 0.0088 0.0955 0.5317 0.020 Uiso 1 1 calc R
H71B H 0.2200 0.0612 0.5548 0.020 Uiso 1 1 calc R
O71 O 0.20668(16) 0.17573(6) 0.63591(10) 0.0237(3) Uani 1 1 d .
H71 H 0.2068 0.1565 0.7138 0.036 Uiso 1 1 calc R
C81 C -0.15047(19) 0.11310(9) 0.19682(14) 0.0143(3) Uani 1 1 d .
H81A H -0.2288 0.1138 0.2618 0.017 Uiso 1 1 calc R
H81B H -0.1461 0.1719 0.1624 0.017 Uiso 1 1 calc R
O81 O -0.23754(13) 0.05851(6) 0.08199(9) 0.0155(2) Uani 1 1 d .
H81 H -0.2233 0.0794 0.0089 0.023 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 0.0033 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'
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
C2 C1 C7 108.61(11)
C2 C1 C6 105.94(11)
C7 C1 C6 109.42(10)
C3 C2 C1 114.51(12)
C2 C3 C4 113.99(12)
C3 C4 C5 108.65(11)
C3 C4 C8 106.52(11)
C5 C4 C8 109.11(10)
C51 C5 C4 112.09(11)
C51 C5 C6 111.46(11)
C4 C5 C6 109.35(10)
C61 C6 C5 110.87(11)
C61 C6 C1 114.10(11)
C5 C6 C1 108.53(10)
C71 C7 C8 111.67(11)
C71 C7 C1 111.65(11)
C8 C7 C1 109.38(10)
C81 C8 C7 110.69(11)
C81 C8 C4 114.32(11)
C7 C8 C4 108.65(10)
O51 C51 C5 112.23(11)
O61 C61 C6 112.99(11)
O71 C71 C7 108.90(11)
O81 C81 C8 112.83(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.5053(19)
C1 C7 1.5496(19)
C1 C6 1.5534(18)
C2 C3 1.3249(19)
C3 C4 1.5084(18)
C4 C5 1.5446(18)
C4 C8 1.5532(18)
C5 C51 1.5216(18)
C5 C6 1.5507(17)
C6 C61 1.5241(19)
C7 C71 1.5176(18)
C7 C8 1.5467(18)
C8 C81 1.5245(18)
C51 O51 1.4420(16)
C61 O61 1.4271(15)
C71 O71 1.4206(16)
C81 O81 1.4361(15)
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
C7 C1 C2 C3 58.72(15)
C6 C1 C2 C3 -58.72(15)
C1 C2 C3 C4 -1.88(18)
C2 C3 C4 C5 58.93(15)
C2 C3 C4 C8 -58.48(15)
C3 C4 C5 C51 73.73(14)
C8 C4 C5 C51 -170.52(11)
C3 C4 C5 C6 -50.40(13)
C8 C4 C5 C6 65.35(13)
C51 C5 C6 C61 102.11(13)
C4 C5 C6 C61 -133.40(11)
C51 C5 C6 C1 -131.82(12)
C4 C5 C6 C1 -7.33(14)
C2 C1 C6 C61 -174.95(11)
C7 C1 C6 C61 68.14(14)
C2 C1 C6 C5 60.88(13)
C7 C1 C6 C5 -56.03(13)
C2 C1 C7 C71 73.47(13)
C6 C1 C7 C71 -171.32(11)
C2 C1 C7 C8 -50.64(14)
C6 C1 C7 C8 64.57(13)
C71 C7 C8 C81 103.04(13)
C1 C7 C8 C81 -132.86(11)
C71 C7 C8 C4 -130.67(12)
C1 C7 C8 C4 -6.57(14)
C3 C4 C8 C81 -175.56(11)
C5 C4 C8 C81 67.34(14)
C3 C4 C8 C7 60.28(13)
C5 C4 C8 C7 -56.83(13)
C4 C5 C51 O51 62.95(14)
C6 C5 C51 O51 -174.11(10)
C5 C6 C61 O61 177.69(10)
C1 C6 C61 O61 54.79(15)
C8 C7 C71 O71 -174.74(11)
C1 C7 C71 O71 62.44(15)
C7 C8 C81 O81 177.73(10)
C4 C8 C81 O81 54.66(15)
