#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:56:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180203 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/97/7109723.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_7109723
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         'C16 H16 N2 O4'
_chemical_formula_sum            'C16 H16 N2 O4'
_chemical_formula_weight         300.31
_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                96.580(2)
_cell_angle_beta                 101.994(2)
_cell_angle_gamma                100.214(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9815(8)
_cell_length_b                   9.9504(10)
_cell_length_c                   10.0645(10)
_cell_measurement_temperature    293(2)
_cell_volume                     759.89(13)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            3962
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         4.19
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.56258
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.008
_exptl_crystal_size_mid          0.006
_exptl_crystal_size_min          0.002
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0470
_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)+(0.0703P)²+0.3827P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1344
_reflns_number_gt                2175
_reflns_number_total             2615
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc44533j.txt
_cod_data_source_block           3a
_cod_database_code               7109723
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 0.20466(19) 0.42118(14) 0.48698(16) 0.0287(4) Uani 1 1 d .
O2 O 0.07220(18) 0.23538(14) 0.56086(14) 0.0231(4) Uani 1 1 d .
O3 O 0.3167(2) 0.00085(14) 0.56671(15) 0.0291(4) Uani 1 1 d .
O4 O 0.45991(19) 0.20690(14) 0.68870(14) 0.0254(4) Uani 1 1 d .
N1 N 0.1550(2) 0.12354(19) -0.03553(19) 0.0311(5) Uani 1 1 d .
N2 N 0.0896(2) 0.02030(17) 0.30615(17) 0.0230(4) Uani 1 1 d .
H2A H 0.0320 -0.0195 0.2251 0.028 Uiso 1 1 calc R
H2B H 0.0630 -0.0100 0.3773 0.028 Uiso 1 1 calc R
C1 C 0.6183(3) 0.4598(2) 0.1572(2) 0.0256(5) Uani 1 1 d .
H1 H 0.5512 0.5270 0.1606 0.031 Uiso 1 1 calc R
C2 C 0.7585(3) 0.4783(2) 0.0940(2) 0.0314(5) Uani 1 1 d .
H2 H 0.7845 0.5578 0.0555 0.038 Uiso 1 1 calc R
C3 C 0.8591(3) 0.3790(2) 0.0882(2) 0.0301(5) Uani 1 1 d .
H3 H 0.9526 0.3913 0.0459 0.036 Uiso 1 1 calc R
C4 C 0.8196(3) 0.2613(2) 0.1460(2) 0.0278(5) Uani 1 1 d .
H4 H 0.8867 0.1941 0.1420 0.033 Uiso 1 1 calc R
C5 C 0.6818(3) 0.2427(2) 0.2093(2) 0.0236(5) Uani 1 1 d .
H5 H 0.6576 0.1633 0.2485 0.028 Uiso 1 1 calc R
C6 C 0.5781(3) 0.34125(19) 0.21544(19) 0.0198(4) Uani 1 1 d .
C7 C 0.4275(2) 0.3225(2) 0.2856(2) 0.0206(4) Uani 1 1 d .
H7 H 0.3752 0.4045 0.2832 0.025 Uiso 1 1 calc R
C8 C 0.2842(2) 0.19377(19) 0.2243(2) 0.0193(4) Uani 1 1 d .
C9 C 0.2210(2) 0.12969(19) 0.32161(19) 0.0186(4) Uani 1 1 d .
C10 C 0.3146(2) 0.21071(19) 0.46408(19) 0.0182(4) Uani 1 1 d .
C11 C 0.4795(2) 0.2983(2) 0.4361(2) 0.0197(4) Uani 1 1 d .
H11A H 0.5752 0.2495 0.4484 0.024 Uiso 1 1 calc R
H11B H 0.5156 0.3857 0.4982 0.024 Uiso 1 1 calc R
C12 C 0.2136(3) 0.1543(2) 0.0815(2) 0.0217(5) Uani 1 1 d .
C13 C 0.1933(3) 0.3039(2) 0.5059(2) 0.0200(4) Uani 1 1 d .
C14 C 0.3610(2) 0.12416(19) 0.5768(2) 0.0187(4) Uani 1 1 d .
C15 C -0.0553(3) 0.3146(2) 0.5932(2) 0.0280(5) Uani 1 1 d .
H15A H 0.0038 0.3949 0.6598 0.042 Uiso 1 1 calc R
H15B H -0.1394 0.2583 0.6302 0.042 Uiso 1 1 calc R
H15C H -0.1141 0.3428 0.5110 0.042 Uiso 1 1 calc R
C16 C 0.5139(3) 0.1416(2) 0.8080(2) 0.0298(5) Uani 1 1 d .
H16A H 0.4122 0.0955 0.8340 0.045 Uiso 1 1 calc R
H16B H 0.5834 0.2107 0.8829 0.045 Uiso 1 1 calc R
H16C H 0.5819 0.0754 0.7857 0.045 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
C13 O2 C15 114.16(15)
C14 O4 C16 116.44(15)
C2 C1 C6 120.44(19)
C3 C2 C1 120.3(2)
C4 C3 C2 119.4(2)
C5 C4 C3 120.6(2)
C4 C5 C6 120.87(19)
C1 C6 C5 118.40(19)
C1 C6 C7 120.23(18)
C5 C6 C7 121.36(17)
C6 C7 C8 114.89(16)
C6 C7 C11 113.96(16)
C8 C7 C11 100.64(15)
C9 C8 C12 123.79(18)
C9 C8 C7 113.00(17)
C12 C8 C7 122.93(17)
N2 C9 C8 129.56(18)
N2 C9 C10 121.11(17)
C8 C9 C10 109.13(16)
C14 C10 C9 115.93(15)
C14 C10 C13 109.15(15)
C9 C10 C13 106.67(15)
C14 C10 C11 111.67(15)
C9 C10 C11 102.56(15)
C13 C10 C11 110.60(15)
C10 C11 C7 105.78(15)
N1 C12 C8 179.1(2)
O1 C13 O2 125.04(18)
O1 C13 C10 123.57(18)
O2 C13 C10 111.35(16)
O3 C14 O4 124.99(18)
O3 C14 C10 126.00(17)
O4 C14 C10 109.01(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.195(2)
O2 C13 1.334(2)
O2 C15 1.458(2)
O3 C14 1.201(2)
O4 C14 1.325(2)
O4 C16 1.453(2)
N1 C12 1.157(3)
N2 C9 1.341(2)
C1 C2 1.393(3)
C1 C6 1.393(3)
C2 C3 1.383(3)
C3 C4 1.382(3)
C4 C5 1.377(3)
C5 C6 1.396(3)
C6 C7 1.510(3)
C7 C8 1.528(3)
C7 C11 1.544(3)
C8 C9 1.361(3)
C8 C12 1.412(3)
C9 C10 1.530(3)
C10 C14 1.526(3)
C10 C13 1.540(3)
C10 C11 1.541(3)
