#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/17/4021791.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_4021791
loop_
_publ_author_name
'Mateo Alajarín'
'José Cabrera'
'Aurelia Pastor'
'Pilar Sánchez-Andrada'
'Delia Bautista'
_publ_section_title
;
 On the [2+2] Cycloaddition of 2-Aminothiazoles and Dimethyl
 Acetylenedicarboxylate. Experimental and Computational Evidence of a
 Thermal Disrotatory Ring Opening of Fused Cyclobutenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5328
_journal_page_last               5339
_journal_paper_doi               10.1021/jo060664c
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C20 H22 N2 O4'
_chemical_formula_weight         354.40
_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           SHELXL-97
_cell_angle_alpha                96.890(2)
_cell_angle_beta                 103.349(2)
_cell_angle_gamma                96.254(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0947(4)
_cell_length_b                   8.6895(5)
_cell_length_c                   13.3367(7)
_cell_measurement_reflns_used    5078
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.92
_cell_measurement_theta_min      2.38
_cell_volume                     897.04(8)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.26
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART APEX'
_diffrn_measurement_method       ω-scan
_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  0.0191
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9919
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9836
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    'rigid methyls, others riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0429
_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)+(0.0453P)²+0.3230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1075
_reflns_number_gt                3411
_reflns_number_total             3629
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo060664csi20060328_073740.cif
_cod_database_code               4021791
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
N1 N 0.66911(16) 0.69685(14) 0.48278(9) 0.0238(3) Uani 1 1 d .
N2 N 0.75732(14) 0.55723(13) 0.61743(9) 0.0189(2) Uani 1 1 d D
O1 O 0.67830(13) 0.89766(12) 0.93098(7) 0.0256(2) Uani 1 1 d .
O2 O 0.58343(13) 1.02494(11) 0.79724(7) 0.0229(2) Uani 1 1 d .
O3 O 0.95196(11) 0.67781(11) 0.96103(7) 0.0208(2) Uani 1 1 d .
O4 O 0.68214(11) 0.55901(11) 0.93877(7) 0.0207(2) Uani 1 1 d .
C1 C 0.78802(16) 0.54217(15) 0.71926(10) 0.0182(3) Uani 1 1 d D
C2 C 0.75484(16) 0.65356(15) 0.79411(10) 0.0171(3) Uani 1 1 d D
C3 C 0.68421(16) 0.78436(15) 0.76002(10) 0.0176(3) Uani 1 1 d D
C4 C 0.65144(16) 0.80034(15) 0.65627(10) 0.0187(3) Uani 1 1 d D
H4 H 0.6022 0.8877 0.6322 0.022 Uiso 1 1 calc R
C5 C 0.69269(16) 0.68359(15) 0.58579(10) 0.0191(3) Uani 1 1 d D
C6 C 0.86048(16) 0.40204(15) 0.74997(10) 0.0189(3) Uani 1 1 d .
H6 H 0.8728 0.3848 0.8202 0.023 Uiso 1 1 calc R
C7 C 0.91004(17) 0.29749(15) 0.68522(11) 0.0195(3) Uani 1 1 d .
H7 H 0.8943 0.3160 0.6151 0.023 Uiso 1 1 calc R
C8 C 0.7017(2) 0.57032(17) 0.41105(11) 0.0254(3) Uani 1 1 d .
H8A H 0.8107 0.5354 0.4419 0.031 Uiso 1 1 calc R
H8B H 0.7077 0.6077 0.3454 0.031 Uiso 1 1 calc R
H8C H 0.6086 0.4826 0.3976 0.031 Uiso 1 1 calc R
C9 C 0.5688(2) 0.81210(18) 0.43908(11) 0.0278(3) Uani 1 1 d .
H9A H 0.4529 0.7931 0.4497 0.033 Uiso 1 1 calc R
H9B H 0.5621 0.8038 0.3643 0.033 Uiso 1 1 calc R
H9C H 0.6235 0.9173 0.4737 0.033 Uiso 1 1 calc R
C10 C 0.64954(16) 0.90644(15) 0.83932(10) 0.0182(3) Uani 1 1 d .
C11 C 0.5524(2) 1.14757(17) 0.87155(12) 0.0280(3) Uani 1 1 d .
H11A H 0.4696 1.1040 0.9076 0.034 Uiso 1 1 calc R
H11B H 0.5062 1.2306 0.8347 0.034 Uiso 1 1 calc R
H11C H 0.6603 1.1910 0.9226 0.034 Uiso 1 1 calc R
C12 C 0.80881(16) 0.63613(15) 0.90710(10) 0.0175(3) Uani 1 1 d .
C13 C 0.72647(18) 0.53807(17) 1.04755(11) 0.0235(3) Uani 1 1 d .
H13A H 0.8261 0.4819 1.0608 0.028 Uiso 1 1 calc R
H13B H 0.6291 0.4775 1.0638 0.028 Uiso 1 1 calc R
H13C H 0.7542 0.6407 1.0916 0.028 Uiso 1 1 calc R
C21 C 0.98601(16) 0.15734(15) 0.71086(10) 0.0186(3) Uani 1 1 d D
C22 C 1.04666(19) 0.06962(16) 0.63593(11) 0.0238(3) Uani 1 1 d D
H22 H 1.0357 0.1009 0.5691 0.029 Uiso 1 1 calc R
C23 C 1.12259(18) -0.06236(16) 0.65701(11) 0.0237(3) Uani 1 1 d D
H23 H 1.1623 -0.1200 0.6044 0.028 Uiso 1 1 calc R
C24 C 1.14155(16) -0.11163(15) 0.75394(11) 0.0198(3) Uani 1 1 d D
C25 C 1.08053(17) -0.02409(16) 0.82911(11) 0.0205(3) Uani 1 1 d D
H25 H 1.0919 -0.0554 0.8959 0.025 Uiso 1 1 calc R
C26 C 1.00405(17) 0.10693(15) 0.80823(10) 0.0196(3) Uani 1 1 d D
H26 H 0.9631 0.1637 0.8607 0.023 Uiso 1 1 calc R
C27 C 1.22477(18) -0.25408(16) 0.77782(12) 0.0251(3) Uani 1 1 d .
H27A H 1.1359 -0.3439 0.7700 0.030 Uiso 1 1 calc R
H27B H 1.2959 -0.2345 0.8495 0.030 Uiso 1 1 calc R
H27C H 1.2967 -0.2767 0.7295 0.030 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'
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
C5 N1 C9 120.13(12)
C5 N1 C8 119.73(11)
C9 N1 C8 117.95(11)
C5 N2 C1 119.23(11)
C10 O2 C11 114.60(10)
C12 O4 C13 114.52(10)
N2 C1 C2 122.67(12)
N2 C1 C6 117.03(12)
C2 C1 C6 120.30(12)
C1 C2 C3 117.74(12)
C1 C2 C12 119.29(11)
C3 C2 C12 122.76(12)
C4 C3 C2 120.04(12)
C4 C3 C10 121.33(12)
C2 C3 C10 118.62(12)
C3 C4 C5 118.58(12)
N2 C5 N1 117.32(12)
N2 C5 C4 121.71(12)
N1 C5 C4 120.97(12)
C7 C6 C1 123.98(12)
C6 C7 C21 126.89(13)
O1 C10 O2 123.83(12)
O1 C10 C3 123.34(12)
O2 C10 C3 112.82(11)
O3 C12 O4 124.09(12)
O3 C12 C2 123.92(12)
O4 C12 C2 111.84(11)
C22 C21 C26 117.55(12)
C22 C21 C7 119.08(12)
C26 C21 C7 123.35(12)
C23 C22 C21 121.32(13)
C22 C23 C24 121.08(13)
C23 C24 C25 117.71(12)
C23 C24 C27 121.49(12)
C25 C24 C27 120.80(12)
C26 C25 C24 121.37(12)
C25 C26 C21 120.96(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C5 1.3634(17)
N1 C9 1.4495(18)
N1 C8 1.4563(17)
N2 C5 1.3385(17)
N2 C1 1.3481(17)
O1 C10 1.2039(16)
O2 C10 1.3347(16)
O2 C11 1.4493(16)
O3 C12 1.2052(16)
O4 C12 1.3405(16)
O4 C13 1.4505(16)
C1 C2 1.3979(18)
C1 C6 1.4693(18)
C2 C3 1.4040(18)
C2 C12 1.4999(18)
C3 C4 1.3744(19)
C3 C10 1.5017(18)
C4 C5 1.4192(18)
C6 C7 1.3354(19)
C7 C21 1.4643(18)
C21 C22 1.3950(19)
C21 C26 1.4009(18)
C22 C23 1.3868(19)
C23 C24 1.3906(19)
C24 C25 1.3983(19)
C24 C27 1.5049(18)
C25 C26 1.3809(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C13 H13A O3 0.98 2.43 3.3849(17) 163.3 2_767
C26 H26 O3 0.95 2.51 3.3262(16) 144.7 2_767
C13 H13B O4 0.98 2.50 3.3753(17) 149.1 2_667
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9755940
