#------------------------------------------------------------------------------
#$Date: 2025-08-21 22:04:39 +0200 (Thu 21 de Aug de 2025) $
#$Revision: 301851 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/25/7052568.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_7052568
loop_
_publ_author_name
'Adak, Laksmikanta'
'Bhadra, Sukalyan'
'Chattopadhyay, Kalicharan'
'Ranu, Brindaban C.'
_publ_section_title
;
 Amphiphilic allylation of activated alkenes by allyl acetates and
 allylstannanes catalyzed by palladium nanoparticles: an easy access to
 stereodefined substituted cyclohexene derivatives
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              430
_journal_paper_doi               10.1039/c0nj00624f
_journal_volume                  35
_journal_year                    2011
_chemical_formula_moiety         'C16 H14 N2 O2'
_chemical_formula_sum            'C16 H14 N2 O2'
_chemical_formula_weight         266.29
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.039(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2763(14)
_cell_length_b                   7.4688(9)
_cell_length_c                   17.260(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1416.2(3)
_computing_cell_refinement       'BRUKER AXS SMART 3'
_computing_data_collection       'BRUKER AXS SMART 3'
_computing_data_reduction        'BRUKER AXS SMART 3'
_computing_molecular_graphics    'BRUKER SHELXLTL'
_computing_publication_material  'BRUKER SHELXLTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'BRUKER AXS SMART 3'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'BRUKER CCD AREA DETECTOR'
_diffrn_measurement_method       'PHI-OMEGA 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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13287
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.97
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9875
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            gray
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.882
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0906P)²+0.1880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1162
_refine_ls_wR_factor_ref         0.1326
_reflns_number_gt                1894
_reflns_number_total             2612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0NJ00624F.TXT
_cod_data_source_block           3a
_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.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7052568
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C13 C 0.66717(14) 1.2148(2) 0.51904(9) 0.0442(4) Uani 1 1 d . . .
C10 C 0.76153(13) 1.0935(2) 0.56464(9) 0.0432(4) Uani 1 1 d . . .
C7 C 0.92447(13) 0.8659(2) 0.67285(9) 0.0428(4) Uani 1 1 d . . .
H7 H 0.8934 0.9268 0.7145 0.051 Uiso 1 1 calc R . .
C12 C 0.81080(13) 0.7827(2) 0.61445(9) 0.0417(4) Uani 1 1 d . . .
C14 C 0.84490(15) 0.7228(2) 0.54040(10) 0.0494(4) Uani 1 1 d . . .
C4 C 1.01323(13) 0.7259(2) 0.71448(9) 0.0418(4) Uani 1 1 d . . .
C9 C 0.88020(14) 1.1290(2) 0.57941(10) 0.0496(4) Uani 1 1 d . . .
H9 H 0.9049 1.2330 0.5579 0.059 Uiso 1 1 calc R . .
C8 C 0.97666(14) 1.0119(2) 0.62848(11) 0.0520(4) Uani 1 1 d . . .
H8A H 1.0320 1.0856 0.6667 0.062 Uiso 1 1 calc R . .
H8B H 1.0231 0.9564 0.5940 0.062 Uiso 1 1 calc R . .
C2 C 1.09517(17) 0.5648(3) 0.83525(11) 0.0644(5) Uani 1 1 d . . .
H2 H 1.0993 0.5471 0.8891 0.077 Uiso 1 1 calc R . .
C11 C 0.71123(13) 0.9265(2) 0.59413(10) 0.0470(4) Uani 1 1 d . . .
H11A H 0.6439 0.8816 0.5535 0.056 Uiso 1 1 calc R . .
H11B H 0.6809 0.9543 0.6411 0.056 Uiso 1 1 calc R . .
C3 C 1.02000(16) 0.6951(2) 0.79454(10) 0.0510(4) Uani 1 1 d . . .
H3 H 0.9729 0.7636 0.8212 0.061 Uiso 1 1 calc R . .
C15 C 0.76398(15) 0.6273(2) 0.65119(10) 0.0521(4) Uani 1 1 d . . .
C5 C 1.08321(15) 0.6192(2) 0.67572(11) 0.0538(4) Uani 1 1 d . . .
H5 H 1.0804 0.6373 0.6220 0.065 Uiso 1 1 calc R . .
C6 C 1.15696(16) 0.4862(3) 0.71700(12) 0.0641(5) Uani 1 1 d . . .
H6 H 1.2019 0.4137 0.6905 0.077 Uiso 1 1 calc R . .
C1 C 1.16426(17) 0.4605(3) 0.79659(12) 0.0672(5) Uani 1 1 d . . .
H1 H 1.2156 0.3732 0.8243 0.081 Uiso 1 1 calc R . .
N2 N 0.87285(16) 0.6850(3) 0.48303(10) 0.0740(5) Uani 1 1 d . . .
N1 N 0.72513(16) 0.5102(3) 0.67971(11) 0.0781(5) Uani 1 1 d . . .
O2 O 0.56197(10) 1.20819(17) 0.52296(7) 0.0589(4) Uani 1 1 d . . .
O1 O 0.70920(10) 1.32836(17) 0.47228(8) 0.0597(4) Uani 1 1 d . . .
C16 C 0.61942(18) 1.4459(3) 0.42471(13) 0.0711(6) Uani 1 1 d . . .
H16A H 0.6582 1.5226 0.3932 0.107 Uiso 1 1 calc R . .
H16B H 0.5825 1.5175 0.4590 0.107 Uiso 1 1 calc R . .
H16C H 0.5581 1.3756 0.3903 0.107 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C13 O1 123.39(15) . . ?
O2 C13 C10 122.95(14) . . ?
O1 C13 C10 113.64(13) . . ?
C9 C10 C13 123.40(14) . . ?
C9 C10 C11 122.65(14) . . ?
C13 C10 C11 113.95(12) . . ?
C4 C7 C8 116.35(12) . . ?
C4 C7 C12 112.85(12) . . ?
C8 C7 C12 108.21(12) . . ?
C15 C12 C14 108.65(13) . . ?
C15 C12 C11 109.52(12) . . ?
C14 C12 C11 109.40(13) . . ?
C15 C12 C7 110.80(13) . . ?
C14 C12 C7 109.86(12) . . ?
C11 C12 C7 108.59(12) . . ?
N2 C14 C12 176.69(18) . . ?
C3 C4 C5 118.27(15) . . ?
C3 C4 C7 118.05(13) . . ?
C5 C4 C7 123.57(14) . . ?
C10 C9 C8 124.17(15) . . ?
C9 C8 C7 112.80(13) . . ?
C3 C2 C1 120.26(17) . . ?
C10 C11 C12 110.16(11) . . ?
C2 C3 C4 121.07(16) . . ?
N1 C15 C12 178.08(19) . . ?
C6 C5 C4 120.15(16) . . ?
C1 C6 C5 120.61(17) . . ?
C6 C1 C2 119.62(17) . . ?
C13 O1 C16 115.59(13) . . ?
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
C13 O2 1.2043(18) . ?
C13 O1 1.3299(19) . ?
C13 C10 1.481(2) . ?
C10 C9 1.331(2) . ?
C10 C11 1.505(2) . ?
C7 C4 1.512(2) . ?
C7 C8 1.524(2) . ?
C7 C12 1.569(2) . ?
C12 C15 1.476(2) . ?
C12 C14 1.484(2) . ?
C12 C11 1.536(2) . ?
C14 N2 1.140(2) . ?
C4 C3 1.386(2) . ?
C4 C5 1.394(2) . ?
C9 C8 1.500(2) . ?
C2 C3 1.375(3) . ?
C2 C1 1.376(3) . ?
C15 N1 1.138(2) . ?
C5 C6 1.385(3) . ?
C6 C1 1.371(3) . ?
O1 C16 1.447(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26948615
2 PubChem 139175972
