#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/27/4022760.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_4022760
loop_
_publ_author_name
'Dhevalapally B. Ramachary'
'Kinthada Ramakumar'
'Vidadala V. Narayana'
_publ_section_title
;
 Organocatalytic Cascade Reactions Based on Push-Pull Dienamine
 Platform: Synthesis of Highly Substituted Anilines
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1458
_journal_page_last               1463
_journal_paper_doi               10.1021/jo0623639
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C16 H17 N O3'
_chemical_formula_sum            'C16 H17 N O3'
_chemical_formula_weight         271.31
_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                 107.064(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9755(12)
_cell_length_b                   8.2031(9)
_cell_length_c                   16.2285(18)
_cell_measurement_reflns_used    6663
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.96
_cell_measurement_theta_min      2.63
_cell_volume                     1396.8(3)
_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  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(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     0.71073
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13983
_diffrn_reflns_theta_full        26.03
_diffrn_reflns_theta_max         26.03
_diffrn_reflns_theta_min         1.94
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.888039
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0516
_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)+(0.0737P)²+0.2976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1404
_reflns_number_gt                2182
_reflns_number_total             2736
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0623639si20061115_125551.cif
_cod_data_source_block           DBR-4aa
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022760
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
O1 O 0.15957(13) 1.29650(14) 0.09657(10) 0.0585(4) Uani 1 1 d .
H1 H 0.1163 1.3684 0.1091 0.088 Uiso 1 1 calc R
O3 O 0.01468(13) 0.54556(16) 0.13257(10) 0.0625(4) Uani 1 1 d .
C4 C 0.01951(15) 0.83732(19) 0.12105(11) 0.0407(4) Uani 1 1 d .
N1 N 0.27980(14) 1.0394(2) 0.05524(10) 0.0467(4) Uani 1 1 d .
O2 O -0.15917(12) 0.68917(15) 0.12585(10) 0.0618(4) Uani 1 1 d .
C5 C 0.12663(15) 0.85556(19) 0.09066(10) 0.0391(4) Uani 1 1 d .
C6 C 0.17268(15) 1.0125(2) 0.08599(10) 0.0405(4) Uani 1 1 d .
C2 C 0.00872(17) 1.1285(2) 0.13914(12) 0.0477(4) Uani 1 1 d .
H2 H -0.0297 1.2185 0.1559 0.057 Uiso 1 1 calc R
C10 C 0.40437(15) 1.0293(2) 0.11112(11) 0.0413(4) Uani 1 1 d .
C3 C -0.03693(17) 0.9746(2) 0.14513(11) 0.0453(4) Uani 1 1 d .
H3 H -0.1070 0.9615 0.1657 0.054 Uiso 1 1 calc R
C1 C 0.11187(16) 1.14855(19) 0.10823(11) 0.0428(4) Uani 1 1 d .
C7 C -0.03786(17) 0.6759(2) 0.12701(12) 0.0452(4) Uani 1 1 d .
C16 C 0.18917(18) 0.7144(2) 0.05972(13) 0.0509(5) Uani 1 1 d .
H16A H 0.2421 0.7546 0.0265 0.076 Uiso 1 1 calc R
H16B H 0.1248 0.6440 0.0246 0.076 Uiso 1 1 calc R
H16C H 0.2405 0.6545 0.1084 0.076 Uiso 1 1 calc R
C11 C 0.43443(17) 0.9411(2) 0.18745(12) 0.0526(5) Uani 1 1 d .
H11 H 0.3703 0.8883 0.2040 0.063 Uiso 1 1 calc R
C15 C 0.50287(17) 1.1053(2) 0.08850(13) 0.0527(5) Uani 1 1 d .
H15 H 0.4849 1.1640 0.0373 0.063 Uiso 1 1 calc R
C12 C 0.55861(19) 0.9315(3) 0.23875(13) 0.0661(6) Uani 1 1 d .
H12 H 0.5775 0.8717 0.2896 0.079 Uiso 1 1 calc R
C14 C 0.62643(18) 1.0953(3) 0.14041(15) 0.0634(6) Uani 1 1 d .
H14 H 0.6911 1.1475 0.1242 0.076 Uiso 1 1 calc R
C8 C -0.2260(2) 0.5417(3) 0.13738(16) 0.0692(6) Uani 1 1 d .
H8A H -0.1992 0.4509 0.1086 0.083 Uiso 1 1 calc R
H8B H -0.2062 0.5160 0.1982 0.083 Uiso 1 1 calc R
C13 C 0.65517(19) 1.0086(3) 0.21638(14) 0.0675(6) Uani 1 1 d .
H13 H 0.7387 1.0023 0.2519 0.081 Uiso 1 1 calc R
C9 C -0.3598(2) 0.5675(3) 0.1019(2) 0.1082(11) Uani 1 1 d .
H9A H -0.3853 0.6591 0.1297 0.162 Uiso 1 1 calc R
H9B H -0.4049 0.4720 0.1108 0.162 Uiso 1 1 calc R
H9C H -0.3792 0.5886 0.0412 0.162 Uiso 1 1 calc R
H1A H 0.2698(18) 1.118(3) 0.0225(13) 0.054(6) Uiso 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
C3 C4 C5 119.77(15)
C3 C4 C7 118.10(15)
C5 C4 C7 122.12(14)
C10 N1 C6 120.84(15)
C7 O2 C8 118.08(14)
C6 C5 C4 118.04(14)
C6 C5 C16 118.98(15)
C4 C5 C16 122.92(15)
C5 C6 C1 120.95(15)
C5 C6 N1 120.83(15)
C1 C6 N1 118.17(15)
C3 C2 C1 119.51(16)
C15 C10 C11 118.08(16)
C15 C10 N1 119.29(16)
C11 C10 N1 122.59(16)
C2 C3 C4 121.42(16)
O1 C1 C2 123.39(15)
O1 C1 C6 116.37(15)
C2 C1 C6 120.24(15)
O3 C7 O2 121.88(16)
O3 C7 C4 126.47(16)
O2 C7 C4 111.64(14)
C12 C11 C10 120.25(18)
C14 C15 C10 121.12(18)
C13 C12 C11 121.3(2)
C15 C14 C13 120.36(19)
C9 C8 O2 108.85(18)
C12 C13 C14 118.89(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3568(19)
O3 C7 1.206(2)
C4 C3 1.395(2)
C4 C5 1.410(2)
C4 C7 1.481(2)
N1 C10 1.404(2)
N1 C6 1.423(2)
O2 C7 1.330(2)
O2 C8 1.455(2)
C5 C6 1.393(2)
C5 C16 1.506(2)
C6 C1 1.401(2)
C2 C3 1.372(2)
C2 C1 1.376(3)
C10 C15 1.388(2)
C10 C11 1.388(3)
C11 C12 1.375(3)
C15 C14 1.373(3)
C12 C13 1.371(3)
C14 C13 1.378(3)
C8 C9 1.427(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17265238
