#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:55:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180323 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/37/7153773.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_7153773
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_moiety         'C22 H17 N O6'
_chemical_formula_sum            'C22 H17 N O6'
_chemical_formula_weight         391.11
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 91.54(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.447(6)
_cell_length_b                   9.631(6)
_cell_length_c                   22.349(13)
_cell_measurement_temperature    296(2)
_cell_volume                     1818(2)
_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_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi-omega scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0233
_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       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            34363
_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         26.362
_diffrn_reflns_theta_min         2.303
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       needle
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   0.985
_exptl_transmission_factor_min   0.977
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3708
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_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          0.1455
_refine_ls_wR_factor_ref         0.1634
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2558
_reflns_number_total             3708
_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               7153773
#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+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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O4 O 0.06109(14) 0.29300(12) 0.65414(5) 0.0493(4) Uani 1 1 d . U
O3 O 0.23035(16) 0.30340(12) 0.73310(5) 0.0555(4) Uani 1 1 d . U
O1 O 0.34175(15) -0.21021(13) 0.77948(5) 0.0558(4) Uani 1 1 d . U
O2 O 0.16840(17) -0.21800(13) 0.70501(6) 0.0652(4) Uani 1 1 d . U
O5 O -0.37986(16) -0.06061(16) 0.64194(7) 0.0713(5) Uani 1 1 d . U
H5 H -0.4292 -0.1042 0.6160 1.000 Uiso 1 1 calc R U
N1 N 0.34551(17) 0.07609(14) 0.77699(6) 0.0486(4) Uani 1 1 d . U
O8 O -0.28380(17) -0.19758(17) 0.54317(6) 0.0739(5) Uani 1 1 d . U
H8 H -0.3710 -0.1894 0.5581 1.000 Uiso 1 1 calc R U
C13 C 0.0364(2) 0.00944(16) 0.65315(7) 0.0385(4) Uani 1 1 d . U
C14 C 0.0931(2) -0.05780(16) 0.59783(7) 0.0395(4) Uani 1 1 d . U
C9 C 0.15259(19) 0.08033(16) 0.69506(7) 0.0387(4) Uani 1 1 d . U
C15 C -0.0156(2) -0.12624(16) 0.55853(7) 0.0417(4) Uani 1 1 d . U
C17 C -0.2398(2) -0.05675(18) 0.62959(8) 0.0476(5) Uani 1 1 d . U
C8 C 0.2484(2) 0.01015(17) 0.73564(7) 0.0410(4) Uani 1 1 d . U
C30 C -0.1196(2) 0.01237(17) 0.66609(8) 0.0447(4) Uani 1 1 d . U
H30A H -0.1506 0.0608 0.6998 0.054 Uiso 1 1 calc R U
C10 C 0.1531(2) 0.23463(17) 0.69658(7) 0.0414(4) Uani 1 1 d . U
C1 C 0.4230(2) 0.00670(19) 0.82431(7) 0.0459(4) Uani 1 1 d . U
C2 C 0.4195(2) -0.13743(19) 0.82565(8) 0.0479(5) Uani 1 1 d . U
C19 C 0.2520(2) -0.05502(18) 0.58282(8) 0.0491(5) Uani 1 1 d . U
H19A H 0.3251 -0.0095 0.6077 0.059 Uiso 1 1 calc R U
C16 C -0.1860(2) -0.13350(18) 0.57300(8) 0.0479(5) Uani 1 1 d . U
C7 C 0.2466(2) -0.14687(18) 0.73780(8) 0.0460(4) Uani 1 1 d . U
C22 C 0.0372(2) -0.18867(19) 0.50622(7) 0.0536(5) Uani 1 1 d . U
H22A H -0.0348 -0.2327 0.4804 0.064 Uiso 1 1 calc R U
C6 C 0.4988(2) 0.0781(2) 0.87130(8) 0.0556(5) Uani 1 1 d . U
H6A H 0.5026 0.1746 0.8712 0.067 Uiso 1 1 calc R U
C11 C 0.0604(3) 0.44490(17) 0.65478(9) 0.0550(5) Uani 1 1 d . U
H11A H 0.1681 0.4798 0.6545 0.066 Uiso 1 1 calc R U
H11B H 0.0110 0.4784 0.6907 0.066 Uiso 1 1 calc R U
C21 C 0.1958(3) -0.1853(2) 0.49274(8) 0.0601(5) Uani 1 1 d . U
H21A H 0.2303 -0.2273 0.4580 0.072 Uiso 1 1 calc R U
C20 C 0.3030(2) -0.1198(2) 0.53086(9) 0.0597(6) Uani 1 1 d . U
H20A H 0.4099 -0.1187 0.5219 0.072 Uiso 1 1 calc R U
C3 C 0.4893(2) -0.2116(2) 0.87173(8) 0.0592(5) Uani 1 1 d . U
H3A H 0.4861 -0.3081 0.8717 0.071 Uiso 1 1 calc R U
C4 C 0.5646(2) -0.1405(3) 0.91822(9) 0.0691(6) Uani 1 1 d . U
H4A H 0.6128 -0.1893 0.9497 0.083 Uiso 1 1 calc R U
C5 C 0.5681(3) 0.0038(2) 0.91793(9) 0.0661(6) Uani 1 1 d . U
H5A H 0.6177 0.0509 0.9495 0.079 Uiso 1 1 calc R U
C12 C -0.0299(3) 0.4945(2) 0.60073(11) 0.0842(8) Uani 1 1 d . U
H12A H -0.0317 0.5942 0.6005 0.126 Uiso 1 1 calc R U
H12B H -0.1364 0.4598 0.6015 0.126 Uiso 1 1 calc R U
H12C H 0.0202 0.4615 0.5654 0.126 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
C10 O4 C11 114.64(14)
C7 O1 C2 122.62(14)
C8 N1 C1 123.10(16)
C30 C13 C14 121.51(15)
C30 C13 C9 118.66(15)
C14 C13 C9 119.79(15)
C19 C14 C15 118.20(15)
C19 C14 C13 121.74(16)
C15 C14 C13 120.05(15)
C8 C9 C10 118.33(15)
C8 C9 C13 123.38(15)
C10 C9 C13 118.03(14)
C22 C15 C14 120.18(17)
C22 C15 C16 119.63(16)
C14 C15 C16 120.18(15)
O5 C17 C30 123.72(17)
O5 C17 C16 118.56(16)
C30 C17 C16 117.69(16)
N1 C8 C9 123.07(16)
N1 C8 C7 116.54(15)
C9 C8 C7 120.36(15)
C13 C30 C17 122.73(16)
O3 C10 O4 122.37(16)
O3 C10 C9 123.81(16)
O4 C10 C9 113.82(15)
C2 C1 N1 118.97(16)
C2 C1 C6 119.03(17)
N1 C1 C6 121.96(18)
C3 C2 C1 121.83(18)
C3 C2 O1 118.47(17)
C1 C2 O1 119.69(16)
C14 C19 C20 120.85(18)
O8 C16 C15 123.56(17)
O8 C16 C17 118.79(17)
C15 C16 C17 117.64(14)
O2 C7 O1 118.17(16)
O2 C7 C8 124.16(16)
O1 C7 C8 117.67(15)
C21 C22 C15 120.36(17)
C5 C6 C1 119.3(2)
O4 C11 C12 108.36(17)
C20 C21 C22 120.03(17)
C21 C20 C19 120.36(18)
C2 C3 C4 119.0(2)
C3 C4 C5 120.04(19)
C6 C5 C4 120.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O4 C10 1.334(2)
O4 C11 1.463(2)
O3 C10 1.226(2)
O1 C7 1.358(2)
O1 C2 1.397(2)
O2 C7 1.190(2)
O5 C17 1.223(2)
N1 C8 1.374(2)
N1 C1 1.399(2)
O8 C16 1.216(2)
C13 C30 1.357(3)
C13 C14 1.486(2)
C13 C9 1.502(2)
C14 C19 1.393(3)
C14 C15 1.416(2)
C9 C8 1.377(2)
C9 C10 1.486(2)
C15 C22 1.398(2)
C15 C16 1.486(3)
C17 C30 1.447(3)
C17 C16 1.544(3)
C8 C7 1.513(3)
C1 C2 1.389(3)
C1 C6 1.396(3)
C2 C3 1.373(3)
C19 C20 1.396(3)
C22 C21 1.381(3)
C6 C5 1.381(3)
C11 C12 1.490(3)
C21 C20 1.380(3)
C3 C4 1.385(3)
C4 C5 1.390(3)
