#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:36:15 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180307 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/21/7152134.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_7152134
loop_
_publ_author_name
'Han, Feng'
'Yang, Lei'
'Li, Zhen'
'Xia, Chungu'
_publ_section_title
;
 Acidic-functionalized ionic liquid as an efficient, green and reusable
 catalyst for hetero-Michael addition of nitrogen, sulfur and oxygen
 nucleophiles to α,β-unsaturated ketones.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              346
_journal_page_last               354
_journal_paper_doi               10.1039/c1ob06346d
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C16 H15 N3 O'
_chemical_formula_weight         265.31
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.257(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.912(4)
_cell_length_b                   13.636(5)
_cell_length_c                   10.633(4)
_cell_measurement_temperature    296(2)
_cell_volume                     1392.9(9)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_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  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0434
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8954
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_correction_T_min  0.9759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.119
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0457
_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)+(0.0670P)²+0.2060P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1423
_reflns_number_gt                1725
_reflns_number_total             2442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ob06346d.txt
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1393.0(9)
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7152134
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
C1 C 0.37006(17) 0.51009(13) 0.28400(18) 0.0553(5) Uani 1 1 d .
C2 C 0.30482(17) 0.49724(13) 0.15387(18) 0.0540(5) Uani 1 1 d .
C3 C 0.2388(2) 0.57478(15) 0.0773(2) 0.0702(6) Uani 1 1 d .
H3 H 0.1924 0.5659 -0.0093 0.084 Uiso 1 1 calc R
C4 C 0.2456(2) 0.66362(16) 0.1354(2) 0.0800(7) Uani 1 1 d .
H4 H 0.2038 0.7171 0.0869 0.096 Uiso 1 1 calc R
C5 C 0.3134(2) 0.67769(16) 0.2661(2) 0.0750(6) Uani 1 1 d .
H5 H 0.3163 0.7402 0.3018 0.090 Uiso 1 1 calc R
C6 C 0.37506(19) 0.60183(15) 0.3423(2) 0.0654(5) Uani 1 1 d .
H6 H 0.4187 0.6110 0.4295 0.078 Uiso 1 1 calc R
C7 C 0.2845(2) 0.34843(14) 0.0065(2) 0.0686(6) Uani 1 1 d .
H7 H 0.1970 0.3752 -0.0462 0.082 Uiso 1 1 calc R
C8 C 0.3981(3) 0.36617(18) -0.0644(2) 0.0907(7) Uani 1 1 d .
H8A H 0.4051 0.4351 -0.0798 0.136 Uiso 1 1 calc R
H8B H 0.3756 0.3319 -0.1458 0.136 Uiso 1 1 calc R
H8C H 0.4854 0.3426 -0.0124 0.136 Uiso 1 1 calc R
C9 C 0.2647(2) 0.24065(15) 0.0268(2) 0.0725(6) Uani 1 1 d .
H9A H 0.2497 0.2079 -0.0565 0.087 Uiso 1 1 calc R
H9B H 0.3503 0.2149 0.0819 0.087 Uiso 1 1 calc R
C10 C 0.14669(19) 0.21422(15) 0.0864(2) 0.0674(6) Uani 1 1 d .
C11 C 0.13396(17) 0.11083(14) 0.12607(18) 0.0611(5) Uani 1 1 d .
C12 C 0.0290(2) 0.08470(18) 0.1851(2) 0.0797(7) Uani 1 1 d .
H12 H -0.0331 0.1322 0.1990 0.096 Uiso 1 1 calc R
C13 C 0.0155(2) -0.0102(2) 0.2234(3) 0.0871(7) Uani 1 1 d .
H13 H -0.0556 -0.0264 0.2628 0.105 Uiso 1 1 calc R
C14 C 0.1052(2) -0.08071(17) 0.2040(2) 0.0786(6) Uani 1 1 d .
H14 H 0.0953 -0.1450 0.2296 0.094 Uiso 1 1 calc R
C15 C 0.2100(2) -0.05670(16) 0.1469(3) 0.0816(7) Uani 1 1 d .
H15 H 0.2724 -0.1047 0.1349 0.098 Uiso 1 1 calc R
C16 C 0.2241(2) 0.03777(15) 0.1070(2) 0.0724(6) Uani 1 1 d .
H16 H 0.2949 0.0529 0.0669 0.087 Uiso 1 1 calc R
N1 N 0.42147(18) 0.42134(13) 0.33413(17) 0.0730(5) Uani 1 1 d .
N2 N 0.39175(19) 0.35647(12) 0.24084(17) 0.0742(5) Uani 1 1 d .
N3 N 0.32009(15) 0.40072(11) 0.13136(15) 0.0610(4) Uani 1 1 d .
O1 O 0.06373(16) 0.27603(12) 0.1008(2) 0.1012(6) 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
N1 C1 C2 108.31(17)
N1 C1 C6 130.71(18)
C2 C1 C6 120.97(17)
N3 C2 C1 104.74(15)
N3 C2 C3 133.69(18)
C1 C2 C3 121.54(18)
C4 C3 C2 116.6(2)
C4 C3 H3 121.7
C2 C3 H3 121.7
C3 C4 C5 122.2(2)
C3 C4 H4 118.9
C5 C4 H4 118.9
C6 C5 C4 121.4(2)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 117.2(2)
C5 C6 H6 121.4
C1 C6 H6 121.4
N3 C7 C9 110.77(17)
N3 C7 C8 109.16(17)
C9 C7 C8 111.41(18)
N3 C7 H7 108.5
C9 C7 H7 108.5
C8 C7 H7 108.5
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C10 C9 C7 115.89(17)
C10 C9 H9A 108.3
C7 C9 H9A 108.3
C10 C9 H9B 108.3
C7 C9 H9B 108.3
H9A C9 H9B 107.4
O1 C10 C11 121.0(2)
O1 C10 C9 120.5(2)
C11 C10 C9 118.43(17)
C16 C11 C12 117.6(2)
C16 C11 C10 122.51(19)
C12 C11 C10 119.86(18)
C13 C12 C11 121.0(2)
C13 C12 H12 119.5
C11 C12 H12 119.5
C14 C13 C12 120.4(2)
C14 C13 H13 119.8
C12 C13 H13 119.8
C13 C14 C15 119.7(2)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C16 120.5(2)
C14 C15 H15 119.7
C16 C15 H15 119.7
C15 C16 C11 120.7(2)
C15 C16 H16 119.6
C11 C16 H16 119.6
N2 N1 C1 108.05(16)
N1 N2 N3 108.95(16)
N2 N3 C2 109.93(15)
N2 N3 C7 121.37(16)
C2 N3 C7 128.22(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.369(2)
C1 C2 1.387(3)
C1 C6 1.392(3)
C2 N3 1.353(2)
C2 C3 1.395(3)
C3 C4 1.354(3)
C3 H3 0.9300
C4 C5 1.400(3)
C4 H4 0.9300
C5 C6 1.362(3)
C5 H5 0.9300
C6 H6 0.9300
C7 N3 1.471(3)
C7 C9 1.505(3)
C7 C8 1.521(3)
C7 H7 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 C10 1.505(3)
C9 H9A 0.9700
C9 H9B 0.9700
C10 O1 1.213(2)
C10 C11 1.486(3)
C11 C16 1.386(3)
C11 C12 1.387(3)
C12 C13 1.373(3)
C12 H12 0.9300
C13 C14 1.359(3)
C13 H13 0.9300
C14 C15 1.366(3)
C14 H14 0.9300
C15 C16 1.374(3)
C15 H15 0.9300
C16 H16 0.9300
N1 N2 1.307(2)
N2 N3 1.348(2)
