#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/66/1516611.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_1516611
loop_
_publ_author_name
'Griesbeck, Axel G.'
'Kramer, Wolfgang'
'Heinrich, Thomas'
'Lex, Johann'
_publ_section_title
;
 Photocyclization of N,N-phthaloylanthranilic amides coupled to ω-amino
 acids with increasing chain lengths
;
_journal_issue                   4
_journal_name_full
'Photochemical & Photobiological Sciences'
_journal_page_first              237
_journal_paper_doi               10.1039/b200448h
_journal_volume                  1
_journal_year                    2002
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_melting_point          415.0(10)
_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                   11.398(1)
_cell_length_b                   15.357(1)
_cell_length_c                   16.312(1)
_cell_measurement_reflns_used    2911
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.55
_cell_volume                     2855.2(4)
_computing_cell_refinement       'Nonius DENZO'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO'
_computing_molecular_graphics    SCHAKAL
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2911
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.55
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.013
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0487P)²+0.7538P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0998
_reflns_number_gt                2244
_reflns_number_total             2911
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b200448h.txt
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '414-416' was changed to '415.0(10)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1516611
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
O1 O 0.19424(10) 0.02309(7) 0.05637(6) 0.0358(3) Uani 1 1 d
N2 N 0.14670(10) 0.14941(7) -0.01340(7) 0.0277(3) Uani 1 1 d
C3 C 0.28160(12) 0.05819(9) -0.07636(9) 0.0293(3) Uani 1 1 d
N4 N 0.28243(12) 0.27675(9) 0.10495(9) 0.0389(3) Uani 1 1 d
O5 O 0.15990(11) 0.38628(7) 0.07114(8) 0.0502(3) Uani 1 1 d
C6 C 0.06011(12) 0.17450(8) 0.04621(8) 0.0277(3) Uani 1 1 d
O7 O 0.03191(11) 0.17999(9) -0.12662(7) 0.0533(3) Uani 1 1 d
C8 C 0.31230(14) 0.18755(11) 0.12652(10) 0.0354(4) Uani 1 1 d
C9 C -0.04115(13) 0.12507(10) 0.05326(10) 0.0377(4) Uani 1 1 d
C10 C 0.07347(12) 0.24888(9) 0.09420(9) 0.0290(3) Uani 1 1 d
C11 C 0.11699(13) 0.14510(10) -0.09529(9) 0.0346(4) Uani 1 1 d
C12 C 0.24433(12) 0.08949(9) 0.00760(8) 0.0279(3) Uani 1 1 d
C13 C 0.34589(13) 0.13327(12) 0.05232(10) 0.0357(4) Uani 1 1 d
C14 C -0.11502(14) 0.22215(11) 0.15569(10) 0.0406(4) Uani 1 1 d
C15 C 0.17706(13) 0.30857(10) 0.08789(9) 0.0343(4) Uani 1 1 d
C16 C 0.20774(13) 0.09100(10) -0.13561(9) 0.0330(3) Uani 1 1 d
C17 C -0.01538(14) 0.27204(10) 0.14874(10) 0.0367(4) Uani 1 1 d
C18 C 0.37504(14) 0.00563(11) -0.09737(10) 0.0384(4) Uani 1 1 d
C19 C 0.39211(15) -0.01308(12) -0.17987(11) 0.0466(4) Uani 1 1 d
C20 C 0.22330(16) 0.07165(12) -0.21798(10) 0.0456(4) Uani 1 1 d
C21 C 0.31732(16) 0.01959(12) -0.23921(11) 0.0497(5) Uani 1 1 d
C22 C -0.12831(15) 0.14888(11) 0.10770(11) 0.0442(4) Uani 1 1 d
H1 H 0.2457(14) 0.1607(9) 0.1576(9) 0.031(4) Uiso 1 1 d
H2 H 0.3798(15) 0.1908(10) 0.1629(10) 0.037(4) Uiso 1 1 d
H3 H 0.4279(16) -0.0194(11) -0.0544(10) 0.047(5) Uiso 1 1 d
H4 H -0.0491(15) 0.0735(11) 0.0177(10) 0.049(5) Uiso 1 1 d
H5 H -0.0048(14) 0.3245(11) 0.1809(10) 0.044(5) Uiso 1 1 d
H6 H -0.1765(16) 0.2392(12) 0.1931(11) 0.052(5) Uiso 1 1 d
H7 H -0.1990(16) 0.1138(12) 0.1121(11) 0.051(5) Uiso 1 1 d
H8 H 0.3917(16) 0.1684(11) 0.0141(11) 0.050(5) Uiso 1 1 d
H9 H 0.4000(17) 0.0862(12) 0.0688(10) 0.051(5) Uiso 1 1 d
H10 H 0.4561(16) -0.0493(12) -0.1958(10) 0.050(5) Uiso 1 1 d
H11 H 0.1693(16) 0.0957(11) -0.2582(12) 0.057(5) Uiso 1 1 d
H12 H 0.244(2) -0.0250(14) 0.0585(12) 0.067(6) Uiso 1 1 d
H13 H 0.3414(18) 0.3111(12) 0.0979(12) 0.056(6) Uiso 1 1 d
H14 H 0.3324(16) 0.0047(13) -0.2948(12) 0.061(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
C11 N2 C6 119.94(11)
C11 N2 C12 112.20(11)
C6 N2 C12 121.65(11)
C16 C3 C18 120.77(14)
C16 C3 C12 110.34(12)
C18 C3 C12 128.88(13)
C15 N4 C8 127.56(14)
C9 C6 C10 119.56(13)
C9 C6 N2 118.74(12)
C10 C6 N2 121.65(12)
N4 C8 C13 112.53(14)
C22 C9 C6 120.47(14)
C6 C10 C17 119.24(13)
C6 C10 C15 123.30(12)
C17 C10 C15 117.40(13)
O7 C11 N2 125.42(14)
O7 C11 C16 127.99(14)
N2 C11 C16 106.59(12)
O1 C12 N2 105.92(11)
O1 C12 C3 113.19(11)
N2 C12 C3 101.46(11)
O1 C12 C13 110.82(12)
N2 C12 C13 113.98(12)
C3 C12 C13 111.11(12)
C8 C13 C12 115.59(13)
C17 C14 C22 119.91(15)
O5 C15 N4 122.94(14)
O5 C15 C10 118.66(14)
N4 C15 C10 118.29(13)
C3 C16 C20 121.54(14)
C3 C16 C11 108.70(12)
C20 C16 C11 129.76(14)
C14 C17 C10 120.70(14)
C3 C18 C19 118.01(16)
C18 C19 C21 121.07(16)
C21 C20 C16 117.77(16)
C20 C21 C19 120.83(16)
C9 C22 C14 120.12(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.4138(17)
N2 C11 1.3795(19)
N2 C6 1.4380(18)
N2 C12 1.4840(17)
C3 C16 1.377(2)
C3 C18 1.380(2)
C3 C12 1.512(2)
N4 C15 1.326(2)
N4 C8 1.455(2)
O5 C15 1.2398(18)
C6 C9 1.386(2)
C6 C10 1.3932(19)
O7 C11 1.2202(18)
C8 C13 1.519(2)
C9 C22 1.382(2)
C10 C17 1.394(2)
C10 C15 1.498(2)
C11 C16 1.481(2)
C12 C13 1.524(2)
C14 C17 1.375(2)
C14 C22 1.379(2)
C16 C20 1.388(2)
C18 C19 1.390(2)
C19 C21 1.384(3)
C20 C21 1.381(3)
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
C11 N2 C6 C9 59.09(18)
C12 N2 C6 C9 -91.04(16)
C11 N2 C6 C10 -118.17(15)
C12 N2 C6 C10 91.70(16)
C15 N4 C8 C13 92.32(19)
C10 C6 C9 C22 -0.3(2)
N2 C6 C9 C22 -177.63(14)
C9 C6 C10 C17 0.2(2)
N2 C6 C10 C17 177.47(13)
C9 C6 C10 C15 -176.96(14)
N2 C6 C10 C15 0.3(2)
C6 N2 C11 O7 18.6(2)
C12 N2 C11 O7 171.37(15)
C6 N2 C11 C16 -161.50(12)
C12 N2 C11 C16 -8.75(16)
C11 N2 C12 O1 -110.21(12)
C6 N2 C12 O1 42.01(15)
C11 N2 C12 C3 8.19(15)
C6 N2 C12 C3 160.41(12)
C11 N2 C12 C13 127.69(13)
C6 N2 C12 C13 -80.09(16)
C16 C3 C12 O1 108.61(14)
C18 C3 C12 O1 -72.29(19)
C16 C3 C12 N2 -4.42(15)
C18 C3 C12 N2 174.68(15)
C16 C3 C12 C13 -125.94(14)
C18 C3 C12 C13 53.2(2)
N4 C8 C13 C12 -86.99(18)
O1 C12 C13 C8 -68.58(17)
N2 C12 C13 C8 50.78(19)
C3 C12 C13 C8 164.67(14)
C8 N4 C15 O5 178.99(15)
C8 N4 C15 C10 2.8(2)
C6 C10 C15 O5 121.66(16)
C17 C10 C15 O5 -55.6(2)
C6 C10 C15 N4 -62.0(2)
C17 C10 C15 N4 120.76(16)
C18 C3 C16 C20 0.9(2)
C12 C3 C16 C20 -179.91(15)
C18 C3 C16 C11 -179.61(14)
C12 C3 C16 C11 -0.43(17)
O7 C11 C16 C3 -174.54(16)
N2 C11 C16 C3 5.58(17)
O7 C11 C16 C20 4.9(3)
N2 C11 C16 C20 -174.99(16)
C22 C14 C17 C10 -0.7(2)
C6 C10 C17 C14 0.3(2)
C15 C10 C17 C14 177.65(14)
C16 C3 C18 C19 0.0(2)
C12 C3 C18 C19 -179.05(15)
C3 C18 C19 C21 -0.3(3)
C3 C16 C20 C21 -1.4(3)
C11 C16 C20 C21 179.28(16)
C16 C20 C21 C19 1.0(3)
C18 C19 C21 C20 -0.1(3)
C6 C9 C22 C14 -0.1(3)
C17 C14 C22 C9 0.6(3)
