#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:00:09 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180205 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/99/7109913.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_7109913
loop_
_publ_author_name
'Ashutosh S. Singh'
'Shih-Sheng Sun'
_publ_section_title
;
 Recyclable nitrate-templated photochemical [2+2] cycloaddition reaction
 promoted by a tripodal receptor
;
_journal_name_full               Chem.Commun.
_journal_page_first              10070
_journal_paper_doi               10.1039/c3cc41268g
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C24 H24 N8 O12'
_chemical_formula_sum            'C24 H24 N8 O13'
_chemical_formula_weight         616.51
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                85.485(5)
_cell_angle_beta                 72.352(5)
_cell_angle_gamma                70.281(5)
_cell_formula_units_Z            1
_cell_length_a                   7.3344(8)
_cell_length_b                   10.0039(11)
_cell_length_c                   10.3610(12)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     681.72(14)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_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  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0321
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5488
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.130
_exptl_absorpt_correction_T_max  0.9948
_exptl_absorpt_correction_T_min  0.9733
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.487
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2316
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2198
_reflns_number_gt                1953
_reflns_number_total             2402
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41268g.txt
_cod_data_source_block           4,4'-tpcb_2
_cod_database_code               7109913
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N3 N 0.9874(3) 0.65466(19) 0.31983(18) 0.0244(5) Uani 1 1 d .
O1 O 1.1137(2) 0.71781(17) 0.26885(17) 0.0314(5) Uani 1 1 d .
O2 O 0.8517(3) 0.70173(19) 0.42834(18) 0.0413(5) Uani 1 1 d .
O3 O 1.0012(3) 0.54597(18) 0.26248(18) 0.0384(5) Uani 1 1 d .
C1 C 0.2346(4) 0.9703(2) 0.5439(2) 0.0302(6) Uani 1 1 d .
H1 H 0.2899 1.0424 0.5044 0.036 Uiso 1 1 calc R
C2 C 0.3311(3) 0.8321(2) 0.4933(2) 0.0274(6) Uani 1 1 d .
H2 H 0.4529 0.8090 0.4202 0.033 Uiso 1 1 calc R
C3 C 0.2478(3) 0.7273(2) 0.5505(2) 0.0223(5) Uani 1 1 d .
C4 C 0.0682(3) 0.7672(2) 0.6570(2) 0.0283(6) Uani 1 1 d .
H4 H 0.0062 0.6984 0.6965 0.034 Uiso 1 1 calc R
C5 C -0.0197(3) 0.9053(3) 0.7051(2) 0.0314(6) Uani 1 1 d .
H5 H -0.1404 0.9316 0.7789 0.038 Uiso 1 1 calc R
C6 C 0.3453(3) 0.5727(2) 0.5090(2) 0.0207(5) Uani 1 1 d .
H6 H 0.2436 0.5346 0.4938 0.025 Uiso 1 1 calc R
C7 C 0.4554(3) 0.4750(2) 0.6095(2) 0.0215(5) Uani 1 1 d .
H7 H 0.4021 0.3941 0.6379 0.026 Uiso 1 1 calc R
C8 C 0.4498(3) 0.5498(2) 0.7313(2) 0.0231(5) Uani 1 1 d .
C9 C 0.5636(3) 0.6384(3) 0.7232(2) 0.0295(6) Uani 1 1 d .
H9 H 0.6569 0.6479 0.6394 0.035 Uiso 1 1 calc R
C10 C 0.5407(4) 0.7122(3) 0.8370(3) 0.0354(6) Uani 1 1 d .
H10 H 0.6185 0.7726 0.8316 0.042 Uiso 1 1 calc R
C11 C 0.2973(4) 0.6153(3) 0.9667(2) 0.0412(7) Uani 1 1 d .
H11 H 0.2045 0.6086 1.0518 0.049 Uiso 1 1 calc R
C12 C 0.3157(4) 0.5386(3) 0.8559(2) 0.0324(6) Uani 1 1 d .
H12 H 0.2368 0.4782 0.8648 0.039 Uiso 1 1 calc R
N1 N 0.0658(3) 1.0031(2) 0.6471(2) 0.0294(5) Uani 1 1 d .
H1' H 0.0084 1.0915 0.6785 0.035 Uiso 1 1 calc R
N2 N 0.4097(3) 0.6990(2) 0.9547(2) 0.0367(6) Uani 1 1 d .
H2' H 0.3968 0.7468 1.0265 0.044 Uiso 1 1 calc R
N4 N 0.6003(4) 0.8727(2) 0.1301(2) 0.0422(6) Uani 1 1 d .
O4 O 0.4409(3) 0.8449(2) 0.1578(2) 0.0542(6) Uani 1 1 d .
O5 O 0.7334(5) 0.8265(4) 0.0235(3) 0.1021(12) Uani 1 1 d .
O6 O 0.6225(5) 0.9450(3) 0.2128(2) 0.0870(10) Uani 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O3 N3 O2 121.24(18) . .
O3 N3 O1 119.38(17) . .
O2 N3 O1 119.38(18) . .
N1 C1 C2 120.7(2) . .
N1 C1 H1 119.6 . .
C2 C1 H1 119.6 . .
C1 C2 C3 119.3(2) . .
C1 C2 H2 120.3 . .
C3 C2 H2 120.3 . .
C2 C3 C4 117.9(2) . .
C2 C3 C6 123.88(19) . .
C4 C3 C6 118.11(19) . .
C5 C4 C3 120.5(2) . .
C5 C4 H4 119.8 . .
C3 C4 H4 119.8 . .
N1 C5 C4 119.7(2) . .
N1 C5 H5 120.2 . .
C4 C5 H5 120.2 . .
C3 C6 C7 119.34(17) . 2_666
C3 C6 C7 115.15(16) . .
C7 C6 C7 90.64(15) 2_666 .
C3 C6 H6 110.1 . .
C7 C6 H6 110.1 2_666 .
C7 C6 H6 110.1 . .
C8 C7 C6 119.19(17) . 2_666
C8 C7 C6 115.59(17) . .
C6 C7 C6 89.36(15) 2_666 .
C8 C7 H7 110.4 . .
C6 C7 H7 110.4 2_666 .
C6 C7 H7 110.4 . .
C12 C8 C9 118.2(2) . .
C12 C8 C7 119.0(2) . .
C9 C8 C7 122.67(19) . .
C10 C9 C8 119.9(2) . .
C10 C9 H9 120.1 . .
C8 C9 H9 120.1 . .
N2 C10 C9 120.1(2) . .
N2 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
N2 C11 C12 120.1(2) . .
N2 C11 H11 119.9 . .
C12 C11 H11 119.9 . .
C11 C12 C8 119.8(2) . .
C11 C12 H12 120.1 . .
C8 C12 H12 120.1 . .
C5 N1 C1 121.8(2) . .
C5 N1 H1' 119.1 . .
C1 N1 H1' 119.1 . .
C10 N2 C11 121.9(2) . .
C10 N2 H2' 119.1 . .
C11 N2 H2' 119.1 . .
O5 N4 O6 121.8(3) . .
O5 N4 O4 119.5(2) . .
O6 N4 O4 118.7(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N3 O3 1.240(2) .
N3 O2 1.251(2) .
N3 O1 1.258(2) .
C1 N1 1.328(3) .
C1 C2 1.384(3) .
C1 H1 0.9500 .
C2 C3 1.392(3) .
C2 H2 0.9500 .
C3 C4 1.395(3) .
C3 C6 1.503(3) .
C4 C5 1.373(3) .
C4 H4 0.9500 .
C5 N1 1.343(3) .
C5 H5 0.9500 .
C6 C7 1.551(3) 2_666
C6 C7 1.584(3) .
C6 H6 1.0000 .
C7 C8 1.501(3) .
C7 C6 1.551(3) 2_666
C7 H7 1.0000 .
C8 C12 1.389(3) .
C8 C9 1.390(3) .
C9 C10 1.377(3) .
C9 H9 0.9500 .
C10 N2 1.333(3) .
C10 H10 0.9500 .
C11 N2 1.335(4) .
C11 C12 1.378(4) .
C11 H11 0.9500 .
C12 H12 0.9500 .
N1 H1' 0.8800 .
N2 H2' 0.8800 .
N4 O5 1.228(4) .
N4 O6 1.243(3) .
N4 O4 1.237(3) .
