#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/85/1508584.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_1508584
loop_
_publ_author_name
'Molleti, Nagaraju'
'Rana, Nirmal K.'
'Singh, Vinod K.'
_publ_section_title
;
 Highly enantioselective conjugate addition of malononitrile to
 2-enoylpyridines with bifunctional organocatalyst.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4322
_journal_page_last               4325
_journal_paper_doi               10.1021/ol3015607
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C17 H13 N3 O,O2'
_chemical_formula_sum            'C17 H13 N3 O3'
_chemical_formula_weight         307.30
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 103.121(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   11.859(5)
_cell_length_b                   5.765(5)
_cell_length_c                   12.062(5)
_cell_measurement_reflns_used    966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.17
_cell_measurement_theta_min      2.74
_cell_volume                     803.1(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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0478
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3699
_diffrn_reflns_theta_full        23.52
_diffrn_reflns_theta_max         23.52
_diffrn_reflns_theta_min         1.73
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.990
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.408
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   5(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2211
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.907
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0674
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1547P)²+0.5485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2043
_reflns_number_gt                1865
_reflns_number_total             2211
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3015607_si_002.cif
_cod_data_source_block           Chiral
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Empirical' changed to
'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1508584
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C1 C 0.6158(4) 0.2084(10) 0.1858(5) 0.0516(14) Uani 1 1 d .
H1 H 0.6624 0.0790 0.2078 0.062 Uiso 1 1 calc R
C2 C 0.6638(4) 0.3993(9) 0.1444(4) 0.0434(13) Uani 1 1 d .
H2 H 0.7394 0.3940 0.1349 0.052 Uiso 1 1 calc R
C3 C 0.5992(4) 0.5947(10) 0.1178(5) 0.0509(14) Uani 1 1 d .
H3 H 0.6299 0.7267 0.0916 0.061 Uiso 1 1 calc R
C4 C 0.4858(4) 0.5915(9) 0.1311(5) 0.0484(13) Uani 1 1 d .
H4 H 0.4392 0.7222 0.1136 0.058 Uiso 1 1 calc R
C5 C 0.4431(3) 0.3930(7) 0.1703(3) 0.0306(10) Uani 1 1 d .
C6 C 0.3212(3) 0.3787(8) 0.1843(4) 0.0365(11) Uani 1 1 d .
C7 C 0.2737(3) 0.1463(8) 0.1981(4) 0.0324(10) Uani 1 1 d .
H7A H 0.3260 0.0664 0.2598 0.039 Uiso 1 1 calc R
H7B H 0.2703 0.0578 0.1290 0.039 Uiso 1 1 calc R
C8 C 0.1523(3) 0.1521(8) 0.2234(3) 0.0312(10) Uani 1 1 d .
H8 H 0.1152 0.2984 0.1940 0.037 Uiso 1 1 calc R
C9 C 0.0773(3) -0.0501(8) 0.1610(3) 0.0276(9) Uani 1 1 d .
H9 H 0.1138 -0.1969 0.1904 0.033 Uiso 1 1 calc R
C10 C 0.0691(3) -0.0421(8) 0.0366(4) 0.0295(9) Uani 1 1 d .
C11 C -0.0410(3) -0.0458(8) 0.1806(3) 0.0306(9) Uani 1 1 d .
C12 C 0.1551(3) 0.1397(8) 0.3495(4) 0.0333(10) Uani 1 1 d .
C13 C 0.2040(4) -0.0511(9) 0.4149(3) 0.0396(11) Uani 1 1 d .
H13 H 0.2347 -0.1730 0.3807 0.047 Uiso 1 1 calc R
C14 C 0.2070(4) -0.0592(10) 0.5292(4) 0.0501(13) Uani 1 1 d .
H14 H 0.2397 -0.1866 0.5720 0.060 Uiso 1 1 calc R
C15 C 0.1621(4) 0.1196(9) 0.5809(4) 0.0473(12) Uani 1 1 d .
H15 H 0.1653 0.1135 0.6586 0.057 Uiso 1 1 calc R
C16 C 0.1120(4) 0.3087(9) 0.5179(4) 0.0428(12) Uani 1 1 d .
H16 H 0.0810 0.4290 0.5529 0.051 Uiso 1 1 calc R
C17 C 0.1083(4) 0.3180(8) 0.4023(4) 0.0378(11) Uani 1 1 d .
H17 H 0.0741 0.4445 0.3598 0.045 Uiso 1 1 calc R
N1 N 0.5057(3) 0.2002(8) 0.1958(3) 0.0452(11) Uani 1 1 d .
N2 N -0.1321(3) -0.0390(8) 0.1969(3) 0.0414(9) Uani 1 1 d .
N3 N 0.0659(3) -0.0311(8) -0.0589(3) 0.0363(9) Uani 1 1 d .
O1 O 0.2657(3) 0.5553(7) 0.1845(5) 0.0903(17) Uani 1 1 d .
O2 O 0.4935(15) 0.571(4) 0.510(3) 0.191(10) Uani 0.50 1 d P
O3 O 0.4173(13) 0.584(3) 0.3933(12) 0.129(5) Uani 0.50 1 d P
O4 O 0.5412(12) 0.820(5) 0.4577(15) 0.380(15) 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'
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
N1 C1 C2 123.4(5) . .
C3 C2 C1 119.2(4) . .
C2 C3 C4 118.0(5) . .
C5 C4 C3 119.4(4) . .
N1 C5 C4 122.9(4) . .
N1 C5 C6 115.4(4) . .
C4 C5 C6 121.6(4) . .
O1 C6 C7 122.7(4) . .
O1 C6 C5 119.5(4) . .
C7 C6 C5 117.8(3) . .
C6 C7 C8 113.6(4) . .
C12 C8 C7 112.9(3) . .
C12 C8 C9 109.3(3) . .
C7 C8 C9 110.3(3) . .
C11 C9 C10 108.4(3) . .
C11 C9 C8 111.7(3) . .
C10 C9 C8 111.5(3) . .
N3 C10 C9 177.8(4) . .
N2 C11 C9 178.8(5) . .
C17 C12 C13 118.7(4) . .
C17 C12 C8 120.4(4) . .
C13 C12 C8 121.0(4) . .
C14 C13 C12 120.4(5) . .
C13 C14 C15 120.4(5) . .
C14 C15 C16 120.3(4) . .
C15 C16 C17 119.7(4) . .
C16 C17 C12 120.5(4) . .
C5 N1 C1 116.9(4) . .
O3 O2 O4 98.3(12) . 2_646
O3 O2 O4 78.1(19) . .
O4 O2 O4 170.3(15) 2_646 .
O2 O4 O2 123.4(10) 2_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.339(6) .
C1 C2 1.383(7) .
C2 C3 1.360(7) .
C3 C4 1.389(6) .
C4 C5 1.378(7) .
C5 N1 1.333(6) .
C5 C6 1.496(5) .
C6 O1 1.213(6) .
C6 C7 1.477(6) .
C7 C8 1.539(5) .
C8 C12 1.515(6) .
C8 C9 1.553(6) .
C9 C11 1.475(5) .
C9 C10 1.481(6) .
C10 N3 1.146(5) .
C11 N2 1.142(5) .
C12 C17 1.390(6) .
C12 C13 1.401(7) .
C13 C14 1.372(6) .
C14 C15 1.373(7) .
C15 C16 1.383(7) .
C16 C17 1.386(6) .
O2 O3 1.49(3) .
O2 O4 1.58(3) 2_646
O2 O4 1.71(3) .
O4 O2 1.58(3) 2_656
