#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/26/7052685.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_7052685
loop_
_publ_author_name
'Majumdar, K. C.'
'Ganai, Sintu'
'Nandi, Raj Kumar'
_publ_section_title
;
 Regioselective synthesis of pyrimidine-annulated spiro-dihydrofurans
 by silver-catalyzed 5-endo-dig cyclization
;
_journal_issue                   7
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1355
_journal_paper_doi               10.1039/c1nj20121b
_journal_volume                  35
_journal_year                    2011
_chemical_formula_sum            'C7 H7.5 Cl0.5 N O2'
_chemical_formula_weight         155.37
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.989(4)
_cell_length_b                   11.905(4)
_cell_length_c                   23.737(7)
_cell_measurement_temperature    293(2)
_cell_volume                     3105.4(18)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38174
_diffrn_reflns_theta_full        23.95
_diffrn_reflns_theta_max         23.95
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.131
_exptl_crystal_density_diffrn    0.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.402
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0413
_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)+(0.0660P)²+2.2203P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1134
_refine_ls_wR_factor_ref         0.1195
_reflns_number_gt                2019
_reflns_number_total             2353
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1nj20121b.txt
_cod_data_source_block           kcm
_cod_original_cell_volume        3105.6(17)
_cod_original_formula_sum        'C7 H7.50 Cl0.50 N O2'
_cod_database_code               7052685
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C15 C -0.0274(3) 0.4669(2) 0.08799(16) 0.0773(10) Uani 1 1 d . . .
H15A H 0.0333 0.4158 0.1018 0.116 Uiso 1 1 calc R . .
H15B H -0.0562 0.4416 0.0520 0.116 Uiso 1 1 calc R . .
H15C H -0.0941 0.4698 0.1141 0.116 Uiso 1 1 calc R . .
C16 C 0.3275(2) 0.7087(2) 0.10505(13) 0.0592(7) Uani 1 1 d . . .
H16A H 0.3521 0.7840 0.0962 0.089 Uiso 1 1 calc R . .
H16B H 0.3770 0.6565 0.0844 0.089 Uiso 1 1 calc R . .
H16C H 0.3373 0.6958 0.1447 0.089 Uiso 1 1 calc R . .
O8 O 0.15531(16) 0.73926(16) -0.00483(7) 0.0480(5) Uani 1 1 d . . .
H9 H -0.107(3) 0.978(3) 0.1405(13) 0.075(9) Uiso 1 1 d . . .
H8B H -0.199(2) 0.934(2) 0.0434(10) 0.054(7) Uiso 1 1 d . . .
H8A H -0.080(2) 1.007(3) 0.0361(12) 0.067(8) Uiso 1 1 d . . .
H13 H 0.1817(19) 0.842(2) 0.0575(8) 0.028(5) Uiso 1 1 d . . .
H8 H 0.212(3) 0.766(3) -0.0172(13) 0.071(11) Uiso 1 1 d . . .
Cl1 Cl 0.15978(7) 0.71411(6) 0.35205(3) 0.0664(3) Uani 1 1 d . . .
O2 O -0.14886(14) 0.64671(14) 0.04759(7) 0.0485(4) Uani 1 1 d . . .
N2 N 0.19998(16) 0.69308(15) 0.08959(8) 0.0394(5) Uani 1 1 d . . .
O1 O -0.04881(15) 0.85019(13) 0.02504(6) 0.0478(4) Uani 1 1 d . . .
N1 N 0.02606(16) 0.57948(15) 0.08209(8) 0.0426(5) Uani 1 1 d . . .
C13 C 0.14448(19) 0.77294(19) 0.05147(9) 0.0362(5) Uani 1 1 d . . .
O3 O 0.20079(16) 0.51403(15) 0.12101(10) 0.0714(6) Uani 1 1 d . . .
C10 C 0.00989(19) 0.78138(17) 0.06542(8) 0.0337(5) Uani 1 1 d . . .
C7 C -0.01618(19) 0.83852(18) 0.12189(9) 0.0381(5) Uani 1 1 d . . .
C11 C -0.04510(19) 0.66429(18) 0.06320(8) 0.0344(5) Uani 1 1 d . . .
C4 C 0.0309(2) 0.80217(18) 0.17758(9) 0.0396(5) Uani 1 1 d . . .
C5 C -0.0154(2) 0.7101(2) 0.20557(10) 0.0521(7) Uani 1 1 d . . .
H5 H -0.0747 0.6663 0.1883 0.063 Uiso 1 1 calc R . .
C12 C 0.1491(2) 0.59253(19) 0.09905(10) 0.0434(6) Uani 1 1 d . . .
C1 C 0.1118(2) 0.7462(2) 0.28405(10) 0.0477(6) Uani 1 1 d . . .
C6 C 0.0247(2) 0.6817(2) 0.25884(10) 0.0544(7) Uani 1 1 d . . .
H6 H -0.0073 0.6195 0.2773 0.065 Uiso 1 1 calc R . .
C3 C 0.1197(3) 0.8650(2) 0.20403(10) 0.0544(7) Uani 1 1 d . . .
H3 H 0.1527 0.9270 0.1857 0.065 Uiso 1 1 calc R . .
C9 C -0.0849(2) 0.9265(2) 0.11207(12) 0.0512(6) Uani 1 1 d . . .
C2 C 0.1601(3) 0.8372(2) 0.25718(11) 0.0594(7) Uani 1 1 d . . .
H2 H 0.2199 0.8802 0.2746 0.071 Uiso 1 1 calc R . .
C8 C -0.1125(3) 0.9406(2) 0.05180(12) 0.0540(7) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N2 C13 121.06(18) . . ?
C12 N2 C16 118.1(2) . . ?
C13 N2 C16 118.54(19) . . ?
C10 O1 C8 110.92(17) . . ?
C11 N1 C12 124.25(18) . . ?
C11 N1 C15 118.74(19) . . ?
C12 N1 C15 116.96(19) . . ?
O8 C13 N2 111.89(19) . . ?
O8 C13 C10 108.05(18) . . ?
N2 C13 C10 108.51(17) . . ?
O1 C10 C11 109.01(17) . . ?
O1 C10 C13 109.52(17) . . ?
C11 C10 C13 108.59(17) . . ?
O1 C10 C7 104.50(17) . . ?
C11 C10 C7 111.32(17) . . ?
C13 C10 C7 113.75(18) . . ?
C9 C7 C4 126.3(2) . . ?
C9 C7 C10 107.9(2) . . ?
C4 C7 C10 125.84(19) . . ?
O2 C11 N1 120.9(2) . . ?
O2 C11 C10 122.73(19) . . ?
N1 C11 C10 116.28(18) . . ?
C5 C4 C3 118.2(2) . . ?
C5 C4 C7 122.2(2) . . ?
C3 C4 C7 119.6(2) . . ?
C6 C5 C4 121.2(2) . . ?
O3 C12 N2 124.5(2) . . ?
O3 C12 N1 118.9(2) . . ?
N2 C12 N1 116.58(19) . . ?
C2 C1 C6 121.0(2) . . ?
C2 C1 Cl1 119.31(19) . . ?
C6 C1 Cl1 119.71(19) . . ?
C1 C6 C5 119.2(2) . . ?
C2 C3 C4 120.9(2) . . ?
C7 C9 C8 112.5(2) . . ?
C1 C2 C3 119.5(2) . . ?
O1 C8 C9 104.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C15 N1 1.470(3) . ?
C16 N2 1.461(3) . ?
O8 C13 1.400(3) . ?
Cl1 C1 1.741(2) . ?
O2 C11 1.217(3) . ?
N2 C12 1.340(3) . ?
N2 C13 1.447(3) . ?
O1 C10 1.416(2) . ?
O1 C8 1.432(3) . ?
N1 C11 1.354(3) . ?
N1 C12 1.420(3) . ?
C13 C10 1.519(3) . ?
O3 C12 1.211(3) . ?
C10 C11 1.520(3) . ?
C10 C7 1.530(3) . ?
C7 C9 1.313(3) . ?
C7 C4 1.484(3) . ?
C4 C5 1.379(3) . ?
C4 C3 1.381(3) . ?
C5 C6 1.381(4) . ?
C1 C2 1.365(4) . ?
C1 C6 1.365(4) . ?
C3 C2 1.378(4) . ?
C9 C8 1.472(4) . ?
