#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:56:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180203 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/97/7109725.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_7109725
loop_
_publ_author_name
'Manas K. Ghorai'
'Ranadeep Talukdar'
'Deo Prakash Tiwari'
_publ_section_title
;
 An efficient synthetic route to carbocyclic enaminonitriles via Lewis
 acid catalysed domino-ring-opening-cyclisation (DROC) of donor-acceptor
 cyclopropanes with malononitrile
;
_journal_name_full               Chem.Commun.
_journal_page_first              8205
_journal_paper_doi               10.1039/c3cc44533j
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C20 H18 N2 O4'
_chemical_formula_sum            'C20 H18 N2 O4'
_chemical_formula_weight         350.36
_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                82.050(5)
_cell_angle_beta                 84.145(5)
_cell_angle_gamma                70.761(5)
_cell_formula_units_Z            2
_cell_length_a                   7.632(5)
_cell_length_b                   10.273(5)
_cell_length_c                   11.899(5)
_cell_measurement_reflns_used    610
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.13
_cell_measurement_theta_min      2.83
_cell_volume                     870.8(8)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_sigmaI/netI    0.0800
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4557
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.22
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.746079
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.0045
_exptl_crystal_size_mid          0.0031
_exptl_crystal_size_min          0.0018
_refine_diff_density_max         0.300
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0630
_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)+(0.0732P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                1917
_reflns_number_total             3005
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44533j.txt
_cod_data_source_block           3k
_cod_original_sg_symbol_H-M      'P-1   '
_cod_database_code               7109725
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
O3 O 0.9660(3) 0.4957(2) 0.16735(18) 0.0274(6) Uani 1 1 d .
C12 C 0.6286(4) 0.4657(3) 0.2431(3) 0.0226(7) Uani 1 1 d .
H12A H 0.5029 0.4824 0.2766 0.027 Uiso 1 1 calc R
H12B H 0.6259 0.5315 0.1760 0.027 Uiso 1 1 calc R
O1 O 0.6551(4) 0.5703(2) 0.5121(2) 0.0392(7) Uani 1 1 d .
O2 O 0.5707(3) 0.7067(2) 0.35033(19) 0.0347(6) Uani 1 1 d .
C13 C 0.7570(4) 0.4800(3) 0.3293(3) 0.0220(7) Uani 1 1 d .
O4 O 1.0068(3) 0.5759(3) 0.3248(2) 0.0390(7) Uani 1 1 d .
C3 C 0.2923(4) 0.1640(3) 0.1079(3) 0.0235(7) Uani 1 1 d .
C14 C 0.8335(4) 0.3310(3) 0.3862(3) 0.0213(7) Uani 1 1 d .
C11 C 0.7114(4) 0.3157(3) 0.2123(3) 0.0215(7) Uani 1 1 d .
H11 H 0.8077 0.3123 0.1506 0.026 Uiso 1 1 calc R
N2 N 0.9246(4) 0.3032(3) 0.4810(2) 0.0281(7) Uani 1 1 d .
H2A H 0.9745 0.2186 0.5090 0.034 Uiso 1 1 calc R
H2B H 0.9334 0.3699 0.5141 0.034 Uiso 1 1 calc R
C2 C 0.2997(4) 0.1824(3) 0.2232(3) 0.0238(7) Uani 1 1 d .
H2 H 0.2125 0.1625 0.2773 0.029 Uiso 1 1 calc R
C8 C 0.4280(4) 0.1939(3) 0.0268(3) 0.0224(7) Uani 1 1 d .
N1 N 0.9100(4) -0.0217(3) 0.3756(3) 0.0349(8) Uani 1 1 d .
C18 C 0.4825(6) 0.8254(3) 0.4125(3) 0.0396(10) Uani 1 1 d .
H18A H 0.3968 0.8034 0.4708 0.059 Uiso 1 1 calc R
H18B H 0.4166 0.9029 0.3613 0.059 Uiso 1 1 calc R
H18C H 0.5754 0.8487 0.4465 0.059 Uiso 1 1 calc R
C10 C 0.5681(4) 0.2594(3) 0.1759(3) 0.0189(7) Uani 1 1 d .
C15 C 0.8033(4) 0.2426(3) 0.3212(3) 0.0211(7) Uani 1 1 d .
C1 C 0.4328(4) 0.2289(3) 0.2559(3) 0.0235(7) Uani 1 1 d .
H1 H 0.4345 0.2407 0.3318 0.028 Uiso 1 1 calc R
C4 C 0.1562(4) 0.1175(3) 0.0707(3) 0.0256(8) Uani 1 1 d .
H4 H 0.0688 0.0953 0.1233 0.031 Uiso 1 1 calc R
C17 C 0.6572(4) 0.5871(3) 0.4102(3) 0.0238(7) Uani 1 1 d .
C6 C 0.2828(5) 0.1358(3) -0.1223(3) 0.0271(8) Uani 1 1 d .
H6 H 0.2769 0.1280 -0.1986 0.032 Uiso 1 1 calc R
C16 C 0.8628(4) 0.0971(3) 0.3498(3) 0.0243(8) Uani 1 1 d .
C19 C 0.9230(5) 0.5236(3) 0.2751(3) 0.0242(8) Uani 1 1 d .
C7 C 0.4192(4) 0.1773(3) -0.0886(3) 0.0231(7) Uani 1 1 d .
H7 H 0.5083 0.1950 -0.1422 0.028 Uiso 1 1 calc R
C5 C 0.1503(5) 0.1046(3) -0.0408(3) 0.0274(8) Uani 1 1 d .
H5 H 0.0581 0.0750 -0.0637 0.033 Uiso 1 1 calc R
C9 C 0.5642(4) 0.2411(3) 0.0645(3) 0.0211(7) Uani 1 1 d .
H9 H 0.6537 0.2604 0.0119 0.025 Uiso 1 1 calc R
C20 C 1.1224(5) 0.5343(3) 0.1117(3) 0.0323(8) Uani 1 1 d .
H20A H 1.0960 0.6327 0.1097 0.048 Uiso 1 1 calc R
H20B H 1.1436 0.5093 0.0355 0.048 Uiso 1 1 calc R
H20C H 1.2314 0.4866 0.1530 0.048 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
C19 O3 C20 115.5(3)
C11 C12 C13 105.8(2)
C17 O2 C18 117.3(3)
C17 C13 C14 114.9(3)
C17 C13 C19 105.2(2)
C14 C13 C19 107.5(2)
C17 C13 C12 113.0(3)
C14 C13 C12 102.3(2)
C19 C13 C12 114.3(3)
C4 C3 C2 122.7(3)
C4 C3 C8 118.8(3)
C2 C3 C8 118.6(3)
N2 C14 C15 129.5(3)
N2 C14 C13 121.0(3)
C15 C14 C13 109.4(3)
C10 C11 C15 115.5(2)
C10 C11 C12 113.4(2)
C15 C11 C12 100.6(2)
C1 C2 C3 121.0(3)
C9 C8 C7 122.8(3)
C9 C8 C3 118.6(3)
C7 C8 C3 118.6(3)
C9 C10 C1 118.9(3)
C9 C10 C11 120.5(3)
C1 C10 C11 120.5(3)
C14 C15 C16 122.8(3)
C14 C15 C11 112.9(3)
C16 C15 C11 124.2(3)
C2 C1 C10 120.9(3)
C5 C4 C3 121.1(3)
O1 C17 O2 123.9(3)
O1 C17 C13 126.8(3)
O2 C17 C13 109.3(3)
C7 C6 C5 119.7(3)
N1 C16 C15 178.5(4)
O4 C19 O3 123.6(3)
O4 C19 C13 123.4(3)
O3 C19 C13 113.0(3)
C6 C7 C8 121.3(3)
C4 C5 C6 120.6(3)
C10 C9 C8 122.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C19 1.337(4)
O3 C20 1.449(4)
C12 C11 1.541(4)
C12 C13 1.541(4)
O1 C17 1.201(4)
O2 C17 1.331(4)
O2 C18 1.447(4)
C13 C17 1.519(4)
C13 C14 1.532(4)
C13 C19 1.533(4)
O4 C19 1.199(4)
C3 C4 1.408(4)
C3 C2 1.420(4)
C3 C8 1.421(4)
C14 N2 1.333(4)
C14 C15 1.358(4)
C11 C10 1.517(4)
C11 C15 1.519(4)
C2 C1 1.365(4)
C8 C9 1.415(4)
C8 C7 1.418(4)
N1 C16 1.158(4)
C10 C9 1.369(4)
C10 C1 1.415(4)
C15 C16 1.414(4)
C4 C5 1.358(5)
C6 C7 1.361(4)
C6 C5 1.412(5)
