#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153771.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_7153771
loop_
_publ_author_name
'Naganaboina, Ram Tilak'
'Nayak, Amrita'
'Peddinti, Rama Krishna'
_publ_section_title
;
 Trifluoroacetic acid-promoted Michael addition-cyclization reactions of
 vinylogous carbamates.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3366
_journal_page_last               3370
_journal_paper_doi               10.1039/c4ob00437j
_journal_volume                  12
_journal_year                    2014
_chemical_formula_sum            'C20 H15 N O4'
_chemical_formula_weight         333.32
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                76.975(3)
_cell_angle_beta                 72.998(3)
_cell_angle_gamma                77.774(3)
_cell_formula_units_Z            2
_cell_length_a                   8.4042(8)
_cell_length_b                   9.8413(9)
_cell_length_c                   10.3659(9)
_cell_measurement_temperature    296(2)
_cell_volume                     788.93(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            27639
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.151
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             336
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     69
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1573
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2618
_reflns_number_total             3226
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ob00437j2.cif
_cod_data_source_block           datam_a
_cod_depositor_comments
'Adding full bibliography for 7153771--7153773.cif.'
_cod_database_code               7153771
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.22655(12) 0.45696(10) 0.48113(10) 0.0462(3) Uani 1 1 d . U
O3 O 0.33443(13) 0.09699(12) 0.23403(10) 0.0504(3) Uani 1 1 d . U
N1 N 0.50624(14) 0.25575(11) 0.50167(11) 0.0346(3) Uani 1 1 d . U
O4 O 0.54930(15) 0.18305(14) 0.07646(10) 0.0603(4) Uani 1 1 d . U
O2 O 0.22406(14) 0.39780(12) 0.28882(11) 0.0574(3) Uani 1 1 d . U
C8 C 0.43328(16) 0.26805(14) 0.39628(13) 0.0353(3) Uani 1 1 d . U
C5 C 0.43478(17) 0.33650(14) 0.60584(14) 0.0364(3) Uani 1 1 d . U
C11 C 0.66127(16) 0.09898(13) 0.37031(13) 0.0336(3) Uani 1 1 d . U
C10 C 0.52526(16) 0.17183(14) 0.31414(13) 0.0346(3) Uani 1 1 d . U
C15 C 0.79476(16) -0.01706(14) 0.32423(13) 0.0347(3) Uani 1 1 d . U
C13 C 0.47525(17) 0.15313(15) 0.19351(14) 0.0387(3) Uani 1 1 d . U
C12 C 0.64358(16) 0.15350(13) 0.48611(13) 0.0359(3) Uani 1 1 d . U
H12 H 0.7147 0.1247 0.5444 0.043 Uiso 1 1 calc R U
C6 C 0.29260(17) 0.43546(15) 0.59292(14) 0.0389(3) Uani 1 1 d . U
C9 C 0.28952(18) 0.37519(15) 0.38164(15) 0.0403(4) Uani 1 1 d . U
C16 C 0.88493(18) -0.10282(15) 0.41367(15) 0.0414(4) Uani 1 1 d . U
H16 H 0.8621 -0.0852 0.5023 0.050 Uiso 1 1 calc R U
C4 C 0.49443(19) 0.32166(16) 0.71978(15) 0.0459(4) Uani 1 1 d . U
H4 H 0.5889 0.2555 0.7302 0.055 Uiso 1 1 calc R U
C7 C 0.21151(19) 0.51666(16) 0.69279(17) 0.0462(4) Uani 1 1 d . U
H7 H 0.1154 0.5811 0.6836 0.055 Uiso 1 1 calc R U
C2 C 0.2718(2) 0.50299(17) 0.80614(16) 0.0472(4) Uani 1 1 d . U
C20 C 0.8356(2) -0.04512(17) 0.19230(16) 0.0490(4) Uani 1 1 d . U
H20 H 0.7795 0.0118 0.1293 0.059 Uiso 1 1 calc R U
C17 C 1.00737(19) -0.21331(16) 0.37360(16) 0.0486(4) Uani 1 1 d . U
H17 H 1.0660 -0.2692 0.4353 0.058 Uiso 1 1 calc R U
C18 C 1.0439(2) -0.24198(17) 0.24322(18) 0.0513(4) Uani 1 1 d . U
H18 H 1.1251 -0.3179 0.2169 0.062 Uiso 1 1 calc R U
C3 C 0.4143(2) 0.40469(17) 0.81824(16) 0.0508(4) Uani 1 1 d . U
H3 H 0.4565 0.3946 0.8940 0.061 Uiso 1 1 calc R U
C19 C 0.9588(2) -0.15676(19) 0.15290(18) 0.0573(5) Uani 1 1 d . U
H19 H 0.9840 -0.1741 0.0640 0.069 Uiso 1 1 calc R U
C1 C 0.1852(2) 0.5927(2) 0.91489(18) 0.0648(5) Uani 1 1 d . U
H1A H 0.2522 0.6631 0.9081 0.097 Uiso 1 1 calc R U
H1B H 0.1717 0.5340 1.0038 0.097 Uiso 1 1 calc R U
H1C H 0.0766 0.6380 0.9020 0.097 Uiso 1 1 calc R U
C14 C 0.2599(2) 0.0902(2) 0.12733(19) 0.0709(6) Uani 1 1 d . U
H14A H 0.2496 0.1811 0.0697 0.106 Uiso 1 1 calc R U
H14B H 0.1504 0.0632 0.1677 0.106 Uiso 1 1 calc R U
H14C H 0.3301 0.0218 0.0735 0.106 Uiso 1 1 calc R U
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
C9 O1 C6 121.91(11)
C13 O3 C14 116.06(12)
C12 N1 C8 108.44(11)
C12 N1 C5 130.11(11)
C8 N1 C5 121.38(11)
N1 C8 C10 108.54(11)
N1 C8 C9 120.78(12)
C10 C8 C9 130.58(13)
C4 C5 C6 118.89(13)
C4 C5 N1 124.23(12)
C6 C5 N1 116.87(13)
C12 C11 C10 106.29(12)
C12 C11 C15 124.09(12)
C10 C11 C15 129.57(13)
C8 C10 C11 107.33(12)
C8 C10 C13 122.26(12)
C11 C10 C13 130.37(13)
C20 C15 C16 117.45(13)
C20 C15 C11 122.19(12)
C16 C15 C11 120.36(12)
O4 C13 O3 123.78(13)
O4 C13 C10 125.85(14)
O3 C13 C10 110.37(11)
N1 C12 C11 109.39(11)
C7 C6 O1 117.23(13)
C7 C6 C5 120.66(14)
O1 C6 C5 122.11(13)
O2 C9 O1 118.45(12)
O2 C9 C8 124.95(14)
O1 C9 C8 116.60(12)
C17 C16 C15 121.26(14)
C3 C4 C5 120.18(14)
C2 C7 C6 120.56(14)
C7 C2 C3 118.58(14)
C7 C2 C1 120.89(16)
C3 C2 C1 120.52(16)
C19 C20 C15 120.89(14)
C18 C17 C16 120.68(14)
C19 C18 C17 118.83(14)
C4 C3 C2 121.12(15)
C18 C19 C20 120.86(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.3659(17)
O1 C6 1.3826(17)
O3 C13 1.3282(18)
O3 C14 1.441(2)
N1 C12 1.3577(15)
N1 C8 1.3729(17)
N1 C5 1.4013(17)
O4 C13 1.1921(17)
O2 C9 1.1997(17)
C8 C10 1.3739(18)
C8 C9 1.4457(19)
C5 C4 1.380(2)
C5 C6 1.391(2)
C11 C12 1.3795(18)
C11 C10 1.4190(18)
C11 C15 1.4767(18)
C10 C13 1.4894(19)
C15 C20 1.386(2)
C15 C16 1.390(2)
C6 C7 1.380(2)
C16 C17 1.3760(19)
C4 C3 1.380(2)
C7 C2 1.380(2)
C2 C3 1.389(2)
C2 C1 1.509(2)
C20 C19 1.385(2)
C17 C18 1.376(2)
C18 C19 1.370(2)
