#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:30:12 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180302 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/16/7151659.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_7151659
loop_
_publ_author_name
'Ramesh, Veera V. E.'
'Roy, Arup'
'Vijayadas, Kuruppanthara N.'
'Kendhale, Amol M.'
'Prabhakaran, Panchami'
'Gonnade, Rajesh'
'Puranik, Vedavati G.'
'Sanjayan, Gangadhar J.'
_publ_section_title
;
 Conformationally rigid aromatic amino acids as potential building
 blocks for abiotic foldamers.
;
_journal_issue                   2
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              367
_journal_page_last               369
_journal_paper_doi               10.1039/C0OB00593B
_journal_volume                  9
_journal_year                    2011
_chemical_formula_moiety         'C21 H14 N2 O7'
_chemical_formula_sum            'C21 H14 N2 O7'
_chemical_formula_weight         406.34
_chemical_melting_point          239.0
_chemical_name_common            Phthalimide
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8387(17)
_cell_length_b                   16.585(2)
_cell_length_c                   19.535(3)
_cell_measurement_reflns_used    4862
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.615
_cell_measurement_theta_min      2.356
_cell_volume                     3835.6(9)
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    'SHELXTL and PLATON'
_computing_publication_material  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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Smart APEX'
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '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  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            23533
_diffrn_reflns_theta_full        23.75
_diffrn_reflns_theta_max         23.75
_diffrn_reflns_theta_min         2.36
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.9878
_exptl_absorpt_correction_T_min  0.9600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0525
_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)+(0.0918P)²+0.8521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2131
_reflns_number_total             2916
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            C0OB00593B.TXT
_cod_data_source_block           C21H14N2O7compound2
_cod_original_cell_volume        3835.6(10)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7151659
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6814(2) -0.11999(14) 0.57432(15) 0.1341(10) Uani 1 1 d . . .
O2 O 0.6461(3) 0.00321(17) 0.61030(16) 0.1498(12) Uani 1 1 d . . .
O4 O 0.9264(2) 0.23305(12) 0.45890(12) 0.1019(7) Uani 1 1 d . . .
O5 O 0.66925(17) 0.12031(10) 0.31346(10) 0.0869(6) Uani 1 1 d . . .
N1 N 0.80117(17) 0.15843(11) 0.39428(12) 0.0711(6) Uani 1 1 d . . .
N2 N 0.5915(4) 0.2713(2) 0.2347(2) 0.1175(12) Uani 1 1 d . . .
C1 C 0.6146(5) -0.1509(3) 0.6311(3) 0.196(3) Uani 1 1 d . . .
H1A H 0.6309 -0.1203 0.6716 0.294 Uiso 1 1 calc R . .
H1B H 0.6330 -0.2065 0.6387 0.294 Uiso 1 1 calc R . .
H1C H 0.5357 -0.1462 0.6203 0.294 Uiso 1 1 calc R . .
C2 C 0.6896(3) -0.0412(2) 0.5701(2) 0.0992(10) Uani 1 1 d . . .
C3 C 0.7612(2) -0.01653(15) 0.51120(13) 0.0735(7) Uani 1 1 d . B .
C4 C 0.8468(2) -0.06605(14) 0.48906(13) 0.0688(7) Uani 1 1 d . . .
H4 H 0.8566 -0.1157 0.5104 0.083 Uiso 1 1 calc R . .
C5 C 0.9197(2) -0.04475(14) 0.43567(12) 0.0633(6) Uani 1 1 d . . .
C6 C 1.0050(2) -0.09698(16) 0.41183(14) 0.0777(8) Uani 1 1 d . . .
H6 H 1.0148 -0.1470 0.4325 0.093 Uiso 1 1 calc R . .
C7 C 1.0725(3) -0.07511(19) 0.35929(17) 0.0948(9) Uani 1 1 d . . .
H7 H 1.1273 -0.1106 0.3434 0.114 Uiso 1 1 calc R . .
C8 C 1.0605(3) 0.00051(19) 0.32874(16) 0.0941(9) Uani 1 1 d . . .
H8 H 1.1088 0.0154 0.2934 0.113 Uiso 1 1 calc R . .
C9 C 0.9797(2) 0.05230(16) 0.34991(13) 0.0772(7) Uani 1 1 d . . .
H9 H 0.9723 0.1022 0.3287 0.093 Uiso 1 1 calc R . .
C10 C 0.9067(2) 0.03123(13) 0.40383(12) 0.0623(6) Uani 1 1 d . . .
C11 C 0.8181(2) 0.08172(13) 0.42680(13) 0.0649(6) Uani 1 1 d . B .
C12 C 0.7460(2) 0.05980(16) 0.47834(15) 0.0741(7) Uani 1 1 d . . .
C14 C 0.8568(3) 0.22896(15) 0.41362(16) 0.0775(8) Uani 1 1 d . . .
C15 C 0.8124(2) 0.29299(14) 0.36828(15) 0.0753(8) Uani 1 1 d . A .
C16 C 0.8410(3) 0.37380(17) 0.36423(18) 0.0980(11) Uani 1 1 d . . .
H16 H 0.8955 0.3964 0.3927 0.118 Uiso 1 1 calc R . .
C17 C 0.7841(4) 0.41944(18) 0.3156(2) 0.1154(15) Uani 1 1 d . A .
H17 H 0.8006 0.4741 0.3119 0.139 Uiso 1 1 calc R . .
C18 C 0.7042(4) 0.3865(2) 0.2727(2) 0.1077(13) Uani 1 1 d . . .
H18 H 0.6684 0.4185 0.2402 0.129 Uiso 1 1 calc R A .
C19 C 0.6782(3) 0.30669(16) 0.27833(17) 0.0862(9) Uani 1 1 d . A .
C20 C 0.7323(2) 0.25926(14) 0.32602(14) 0.0721(7) Uani 1 1 d . . .
C21 C 0.7250(2) 0.17140(14) 0.34103(14) 0.0687(7) Uani 1 1 d . A .
O6 O 0.6052(11) 0.2955(8) 0.1779(6) 0.224(6) Uani 0.50 1 d P A 1
O7 O 0.5081(10) 0.2481(6) 0.2639(5) 0.120(3) Uani 0.50 1 d P A 1
O7' O 0.5043(15) 0.2657(11) 0.2422(10) 0.231(9) Uani 0.50 1 d P A 2
O6' O 0.6202(10) 0.2347(5) 0.1806(5) 0.169(4) Uani 0.50 1 d P A 2
O3 O 0.6587(3) 0.1085(5) 0.4892(5) 0.072(2) Uani 0.50 1 d P B 3
C13 C 0.6697(9) 0.1666(7) 0.5373(7) 0.093(3) Uani 0.50 1 d P B 3
C13' C 0.671(2) 0.1813(13) 0.5471(14) 0.232(12) Uani 0.50 1 d P B 4
O3' O 0.6448(10) 0.1090(8) 0.5005(7) 0.170(6) Uani 0.50 1 d P B 4
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
C2 O1 C1 116.0(3) . . ?
C21 N1 C14 112.2(2) . . ?
C21 N1 C11 123.88(19) . . ?
C14 N1 C11 123.9(2) . . ?
O7' N2 O6 107.2(13) . . ?
O7' N2 O7 25.3(13) . . ?
O6 N2 O7 131.3(9) . . ?
O7' N2 O6' 109.8(13) . . ?
O6 N2 O6' 49.1(7) . . ?
O7 N2 O6' 117.5(8) . . ?
O7' N2 C19 130.4(12) . . ?
O6 N2 C19 108.3(7) . . ?
O7 N2 C19 115.5(6) . . ?
O6' N2 C19 119.5(6) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 O1 122.8(3) . . ?
O2 C2 C3 125.9(3) . . ?
O1 C2 C3 111.3(3) . . ?
C4 C3 C12 118.7(2) . . ?
C4 C3 C2 120.0(3) . . ?
C12 C3 C2 121.2(3) . . ?
C3 C4 C5 122.6(2) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 C10 119.1(2) . . ?
C6 C5 C10 118.7(2) . . ?
C7 C6 C5 120.7(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C5 118.9(2) . . ?
C9 C10 C11 123.1(2) . . ?
C5 C10 C11 117.9(2) . . ?
C12 C11 C10 122.6(2) . . ?
C12 C11 N1 118.2(2) . . ?
C10 C11 N1 119.2(2) . . ?
O3 C12 C11 116.1(4) . . ?
O3 C12 C3 124.4(4) . . ?
C11 C12 C3 119.1(2) . . ?
O3 C12 O3' 8.3(8) . . ?
C11 C12 O3' 124.1(5) . . ?
C3 C12 O3' 116.7(5) . . ?
O4 C14 N1 124.5(3) . . ?
O4 C14 C15 129.7(3) . . ?
N1 C14 C15 105.8(3) . . ?
C20 C15 C16 121.8(3) . . ?
C20 C15 C14 108.2(2) . . ?
C16 C15 C14 130.0(3) . . ?
C15 C16 C17 116.7(4) . . ?
C15 C16 H16 121.7 . . ?
C17 C16 H16 121.7 . . ?
C18 C17 C16 122.2(3) . . ?
C18 C17 H17 118.9 . . ?
C16 C17 H17 118.9 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 120.2(4) . . ?
C18 C19 N2 120.2(3) . . ?
C20 C19 N2 119.6(3) . . ?
C15 C20 C19 119.6(3) . . ?
C15 C20 C21 108.6(2) . . ?
C19 C20 C21 131.7(3) . . ?
O5 C21 N1 125.5(2) . . ?
O5 C21 C20 129.3(3) . . ?
N1 C21 C20 105.1(2) . . ?
C12 O3 C13 117.9(6) . . ?
C12 O3' C13' 115.6(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
O1 C2 1.313(4) . ?
O1 C1 1.455(5) . ?
O2 C2 1.193(4) . ?
O4 C14 1.211(3) . ?
O5 C21 1.201(3) . ?
N1 C21 1.393(3) . ?
N1 C14 1.394(3) . ?
N1 C11 1.436(3) . ?
N2 O7' 1.047(17) . ?
N2 O6 1.191(11) . ?
N2 O7 1.203(11) . ?
N2 O6' 1.266(9) . ?
N2 C19 1.457(5) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.487(4) . ?
C3 C4 1.374(4) . ?
C3 C12 1.431(4) . ?
C4 C5 1.399(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.409(4) . ?
C5 C10 1.414(3) . ?
C6 C7 1.351(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.396(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.351(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.407(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.415(3) . ?
C11 C12 1.369(4) . ?
C12 O3 1.329(7) . ?
C12 O3' 1.513(11) . ?
C14 C15 1.479(4) . ?
C15 C20 1.376(4) . ?
C15 C16 1.384(4) . ?
C16 C17 1.388(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.364(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C20 C21 1.489(3) . ?
O3 C13 1.353(16) . ?
C13' O3' 1.54(2) . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 0.6(6) . . . . ?
C1 O1 C2 C3 179.0(4) . . . . ?
O2 C2 C3 C4 149.0(4) . . . . ?
O1 C2 C3 C4 -29.4(4) . . . . ?
O2 C2 C3 C12 -28.5(5) . . . . ?
O1 C2 C3 C12 153.2(3) . . . . ?
C12 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C5 -177.5(2) . . . . ?
C3 C4 C5 C6 -178.0(2) . . . . ?
C3 C4 C5 C10 1.2(4) . . . . ?
C4 C5 C6 C7 178.7(3) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C6 C7 C8 C9 -1.6(5) . . . . ?
C7 C8 C9 C10 0.7(5) . . . . ?
C8 C9 C10 C5 0.3(4) . . . . ?
C8 C9 C10 C11 -177.8(3) . . . . ?
C4 C5 C10 C9 -179.7(2) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C4 C5 C10 C11 -1.4(3) . . . . ?
C6 C5 C10 C11 177.8(2) . . . . ?
C9 C10 C11 C12 178.5(2) . . . . ?
C5 C10 C11 C12 0.3(4) . . . . ?
C9 C10 C11 N1 -0.3(4) . . . . ?
C5 C10 C11 N1 -178.5(2) . . . . ?
C21 N1 C11 C12 -83.9(3) . . . . ?
C14 N1 C11 C12 94.2(3) . . . . ?
C21 N1 C11 C10 94.9(3) . . . . ?
C14 N1 C11 C10 -86.9(3) . . . . ?
C10 C11 C12 O3 -172.2(4) . . . . ?
N1 C11 C12 O3 6.6(5) . . . . ?
C10 C11 C12 C3 0.9(4) . . . . ?
N1 C11 C12 C3 179.8(2) . . . . ?
C10 C11 C12 O3' -174.9(7) . . . . ?
N1 C11 C12 O3' 3.9(8) . . . . ?
C4 C3 C12 O3 171.4(5) . . . . ?
C2 C3 C12 O3 -11.1(6) . . . . ?
C4 C3 C12 C11 -1.1(4) . . . . ?
C2 C3 C12 C11 176.4(3) . . . . ?
C4 C3 C12 O3' 175.0(7) . . . . ?
C2 C3 C12 O3' -7.5(7) . . . . ?
C21 N1 C14 O4 179.6(3) . . . . ?
C11 N1 C14 O4 1.3(4) . . . . ?
C21 N1 C14 C15 -0.3(3) . . . . ?
C11 N1 C14 C15 -178.6(2) . . . . ?
O4 C14 C15 C20 -178.5(3) . . . . ?
N1 C14 C15 C20 1.4(3) . . . . ?
O4 C14 C15 C16 2.1(5) . . . . ?
N1 C14 C15 C16 -178.0(3) . . . . ?
C20 C15 C16 C17 0.4(4) . . . . ?
C14 C15 C16 C17 179.7(3) . . . . ?
C15 C16 C17 C18 -0.8(5) . . . . ?
C16 C17 C18 C19 1.0(5) . . . . ?
C17 C18 C19 C20 -0.8(5) . . . . ?
C17 C18 C19 N2 178.2(3) . . . . ?
O7' N2 C19 C18 -89.6(15) . . . . ?
O6 N2 C19 C18 44.0(10) . . . . ?
O7 N2 C19 C18 -114.1(6) . . . . ?
O6' N2 C19 C18 96.8(6) . . . . ?
O7' N2 C19 C20 89.4(15) . . . . ?
O6 N2 C19 C20 -137.0(9) . . . . ?
O7 N2 C19 C20 64.9(7) . . . . ?
O6' N2 C19 C20 -84.2(6) . . . . ?
C16 C15 C20 C19 -0.2(4) . . . . ?
C14 C15 C20 C19 -179.7(2) . . . . ?
C16 C15 C20 C21 177.5(2) . . . . ?
C14 C15 C20 C21 -1.9(3) . . . . ?
C18 C19 C20 C15 0.4(4) . . . . ?
N2 C19 C20 C15 -178.6(3) . . . . ?
C18 C19 C20 C21 -176.8(3) . . . . ?
N2 C19 C20 C21 4.2(5) . . . . ?
C14 N1 C21 O5 177.4(3) . . . . ?
C11 N1 C21 O5 -4.2(4) . . . . ?
C14 N1 C21 C20 -0.8(3) . . . . ?
C11 N1 C21 C20 177.5(2) . . . . ?
C15 C20 C21 O5 -176.4(3) . . . . ?
C19 C20 C21 O5 1.0(5) . . . . ?
C15 C20 C21 N1 1.7(3) . . . . ?
C19 C20 C21 N1 179.1(3) . . . . ?
C11 C12 O3 C13 -94.0(8) . . . . ?
C3 C12 O3 C13 93.3(7) . . . . ?
O3' C12 O3 C13 70(5) . . . . ?
O3 C12 O3' C13' -96(6) . . . . ?
C11 C12 O3' C13' -79.3(15) . . . . ?
C3 C12 O3' C13' 104.8(14) . . . . ?
