#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:35:41 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180269 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/55/7115541.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_7115541
loop_
_publ_author_name
'Etienne Pair'
'Christophe Berini'
'Romain Noel'
'Morgane Sanselme'
'Vincent Levacher'
'Jean-Francois Briere'
_publ_section_title
;
 Organocatalysed multicomponent synthesis of pyrazolidinones: Meldrum's
 acid approach
;
_journal_name_full               Chem.Commun.
_journal_page_first              10218
_journal_paper_doi               10.1039/C4cc04852k
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C16 H20 N2 O2'
_chemical_formula_sum            'C16 H20 N2 O2'
_chemical_formula_weight         272.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2014-02-27T10:35:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.888(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.1563(13)
_cell_length_b                   8.2068(17)
_cell_length_c                   14.895(3)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_measurement_wavelength     0.71073
_cell_volume                     739.0(3)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5755
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_refine_diff_density_max         0.549
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2952
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.324
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0561
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0544P)²+0.0274P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1288
_refine_ls_wR_factor_ref         0.1345
_reflns_number_gt                2264
_reflns_number_total             2952
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4cc04852k2.cif
_cod_data_source_block           ep305
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7115541
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 0.3722(5) 0.1018(4) 0.9607(2) 0.0545(7) Uani 1 1 d .
H1 H 0.5031 0.0461 0.9593 0.065 Uiso 1 1 calc R
C2 C 0.2064(6) 0.1000(4) 0.8850(2) 0.0679(9) Uani 1 1 d .
H2 H 0.2243 0.0413 0.8335 0.082 Uiso 1 1 calc R
C3 C 0.0167(6) 0.1835(5) 0.8849(2) 0.0719(10) Uani 1 1 d .
H3 H -0.0957 0.1828 0.8335 0.086 Uiso 1 1 calc R
C4 C -0.0077(5) 0.2690(4) 0.9612(2) 0.0693(10) Uani 1 1 d .
H4 H -0.1376 0.3269 0.961 0.083 Uiso 1 1 calc R
C5 C 0.1533(5) 0.2713(4) 1.0373(2) 0.0532(7) Uani 1 1 d .
H5 H 0.1333 0.3307 1.0882 0.064 Uiso 1 1 calc R
C6 C 0.3486(4) 0.1845(3) 1.03896(18) 0.0435(6) Uani 1 1 d .
C7 C 0.5272(5) 0.1828(4) 1.12445(19) 0.0518(7) Uani 1 1 d .
H7A H 0.6636 0.2244 1.1096 0.062 Uiso 1 1 calc R
H7B H 0.484 0.2549 1.1696 0.062 Uiso 1 1 calc R
C8 C 0.5684(4) 0.0137(3) 1.16524(17) 0.0459(6) Uani 1 1 d .
H8A H 0.6111 -0.0578 1.1197 0.055 Uiso 1 1 calc R
H8B H 0.4312 -0.0276 1.1794 0.055 Uiso 1 1 calc R
C9 C 0.7455(4) 0.0070(4) 1.25112(18) 0.0464(6) Uani 1 1 d .
H9 H 0.7628 -0.1054 1.2736 0.056 Uiso 1 1 calc R
C10 C 0.5602(4) 0.1023(4) 1.38336(17) 0.0477(7) Uani 1 1 d .
C11 C 0.6002(5) 0.2538(4) 1.4415(2) 0.0598(8) Uani 1 1 d .
H11A H 0.6555 0.2246 1.5048 0.072 Uiso 1 1 calc R
H11B H 0.4632 0.3137 1.4383 0.072 Uiso 1 1 calc R
C12 C 0.7710(4) 0.3592(3) 1.40514(17) 0.0456(7) Uani 1 1 d .
C13 C 0.9921(4) 0.2385(4) 1.28672(18) 0.0455(7) Uani 1 1 d .
C14 C 0.9694(4) 0.0748(4) 1.2408(2) 0.0492(7) Uani 1 1 d .
H14A H 1.0871 0.0026 1.2695 0.059 Uiso 1 1 calc R
H14B H 0.9772 0.0858 1.1767 0.059 Uiso 1 1 calc R
C15 C 0.9741(5) 0.3919(5) 1.4767(2) 0.0684(9) Uani 1 1 d .
H15A H 1.0324 0.2907 1.5033 0.103 Uiso 1 1 calc R
H15B H 0.9358 0.4607 1.5235 0.103 Uiso 1 1 calc R
H15C H 1.0837 0.4452 1.449 0.103 Uiso 1 1 calc R
C16 C 0.6720(6) 0.5156(5) 1.3628(2) 0.0759(10) Uani 1 1 d .
H16A H 0.779 0.5717 1.3349 0.114 Uiso 1 1 calc R
H16B H 0.6302 0.5833 1.4093 0.114 Uiso 1 1 calc R
H16C H 0.5438 0.4914 1.3172 0.114 Uiso 1 1 calc R
N1 N 0.6925(4) 0.1131(3) 1.32274(15) 0.0488(6) Uani 1 1 d .
N2 N 0.8260(4) 0.2515(3) 1.33215(16) 0.0509(6) Uani 1 1 d .
O1 O 1.1313(3) 0.3426(3) 1.28392(14) 0.0627(6) Uani 1 1 d .
O2 O 0.4358(3) -0.0084(3) 1.39009(14) 0.0691(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 0 '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 0.006 '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
C2 C1 C6 121.3(3)
C2 C1 H1 119.4
C6 C1 H1 119.4
C3 C2 C1 120.3(3)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 119.3(3)
C2 C3 H3 120.4
C4 C3 H3 120.4
C5 C4 C3 121.5(3)
C5 C4 H4 119.2
C3 C4 H4 119.2
C4 C5 C6 120.0(3)
C4 C5 H5 120
C6 C5 H5 120
C1 C6 C5 117.7(3)
C1 C6 C7 121.9(2)
C5 C6 C7 120.4(2)
C8 C7 C6 112.6(2)
C8 C7 H7A 109.1
C6 C7 H7A 109.1
C8 C7 H7B 109.1
C6 C7 H7B 109.1
H7A C7 H7B 107.8
C7 C8 C9 114.2(2)
C7 C8 H8A 108.7
C9 C8 H8A 108.7
C7 C8 H8B 108.7
C9 C8 H8B 108.7
H8A C8 H8B 107.6
N1 C9 C8 111.7(2)
N1 C9 C14 100.8(2)
C8 C9 C14 115.0(2)
N1 C9 H9 109.7
C8 C9 H9 109.7
C14 C9 H9 109.7
O2 C10 N1 126.0(3)
O2 C10 C11 127.7(3)
N1 C10 C11 106.3(2)
C10 C11 C12 108.1(2)
C10 C11 H11A 110.1
C12 C11 H11A 110.1
C10 C11 H11B 110.1
C12 C11 H11B 110.1
H11A C11 H11B 108.4
N2 C12 C15 110.5(2)
N2 C12 C16 109.3(2)
C15 C12 C16 111.1(3)
N2 C12 C11 100.8(2)
C15 C12 C11 112.5(3)
C16 C12 C11 112.2(3)
O1 C13 N2 125.0(3)
O1 C13 C14 128.2(2)
N2 C13 C14 106.8(2)
C13 C14 C9 106.8(2)
C13 C14 H14A 110.4
C9 C14 H14A 110.4
C13 C14 H14B 110.4
C9 C14 H14B 110.4
H14A C14 H14B 108.6
C12 C15 H15A 109.5
C12 C15 H15B 109.5
H15A C15 H15B 109.5
C12 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C12 C16 H16A 109.5
C12 C16 H16B 109.5
H16A C16 H16B 109.5
C12 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C10 N1 N2 114.3(2)
C10 N1 C9 135.0(2)
N2 N1 C9 110.49(19)
C13 N2 N1 112.2(2)
C13 N2 C12 136.1(2)
N1 N2 C12 110.24(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.371(4)
C1 C6 1.380(4)
C1 H1 0.93
C2 C3 1.354(5)
C2 H2 0.93
C3 C4 1.369(5)
C3 H3 0.93
C4 C5 1.357(4)
C4 H4 0.93
C5 C6 1.394(4)
C5 H5 0.93
C6 C7 1.517(4)
C7 C8 1.517(4)
C7 H7A 0.97
C7 H7B 0.97
C8 C9 1.517(4)
C8 H8A 0.97
C8 H8B 0.97
C9 N1 1.461(4)
C9 C14 1.521(4)
C9 H9 0.98
C10 O2 1.205(3)
C10 N1 1.328(3)
C10 C11 1.508(4)
C11 C12 1.537(4)
C11 H11A 0.97
C11 H11B 0.97
C12 N2 1.489(3)
C12 C15 1.506(4)
C12 C16 1.507(5)
C13 O1 1.217(3)
C13 N2 1.332(3)
C13 C14 1.502(4)
C14 H14A 0.97
C14 H14B 0.97
C15 H15A 0.96
C15 H15B 0.96
C15 H15C 0.96
C16 H16A 0.96
C16 H16B 0.96
C16 H16C 0.96
N1 N2 1.393(3)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C6 C1 C2 C3 1.6(5)
C1 C2 C3 C4 -0.2(5)
C2 C3 C4 C5 -0.4(5)
C3 C4 C5 C6 -0.3(5)
C2 C1 C6 C5 -2.3(4)
C2 C1 C6 C7 177.8(3)
C4 C5 C6 C1 1.6(4)
C4 C5 C6 C7 -178.5(3)
C1 C6 C7 C8 -63.4(4)
C5 C6 C7 C8 116.8(3)
C6 C7 C8 C9 -179.8(2)
C7 C8 C9 N1 58.1(3)
C7 C8 C9 C14 -56.0(3)
O2 C10 C11 C12 -179.1(3)
N1 C10 C11 C12 1.6(3)
C10 C11 C12 N2 -3.8(3)
C10 C11 C12 C15 -121.4(3)
C10 C11 C12 C16 112.4(3)
O1 C13 C14 C9 -169.3(3)
N2 C13 C14 C9 10.1(3)
N1 C9 C14 C13 -15.6(3)
C8 C9 C14 C13 104.7(3)
O2 C10 N1 N2 -177.7(3)
C11 C10 N1 N2 1.6(3)
O2 C10 N1 C9 -3.3(5)
C11 C10 N1 C9 176.0(3)
C8 C9 N1 C10 79.4(4)
C14 C9 N1 C10 -158.0(3)
C8 C9 N1 N2 -106.2(3)
C14 C9 N1 N2 16.5(3)
O1 C13 N2 N1 179.9(3)
C14 C13 N2 N1 0.5(3)
O1 C13 N2 C12 -15.7(5)
C14 C13 N2 C12 164.9(3)
C10 N1 N2 C13 164.2(2)
C9 N1 N2 C13 -11.5(3)
C10 N1 N2 C12 -4.4(3)
C9 N1 N2 C12 179.9(2)
C15 C12 N2 C13 -40.8(4)
C16 C12 N2 C13 81.8(4)
C11 C12 N2 C13 -159.9(3)
C15 C12 N2 N1 123.9(3)
C16 C12 N2 N1 -113.5(3)
C11 C12 N2 N1 4.8(3)
