#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:21:29 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180179 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/75/7107582.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_7107582
loop_
_publ_author_name
'Jonathan P. Hill'
'Navaneetha K. Subbaiyan'
'Francis DfSouza'
'Yonshu Xie'
'Satyajit Sahu'
'Noelia M. Sanchez-Ballester'
'Gary J. Richards'
'Toshiyuki Mori'
'Katsuhiko Ariga'
_publ_section_title
;
 Antioxidant-substituted Tetrapyrazinoporphyrinazine as a Turn-on
 Fluorescent Sensor for Basic Anions
;
_journal_name_full               Chem.Commun.
_journal_page_first              3951
_journal_paper_doi               10.1039/c2cc30712j
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C20 H21 Cl N4 O'
_chemical_formula_weight         368.86
_chemical_name_systematic
;
?
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   'except OH'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.394(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.639(5)
_cell_length_b                   6.969(3)
_cell_length_c                   13.260(6)
_cell_measurement_reflns_used    2327
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.16
_cell_measurement_theta_min      3.22
_cell_volume                     927.4(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0316
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7235
_diffrn_reflns_theta_full        27.04
_diffrn_reflns_theta_max         27.04
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10, Sheldrick, G.M., (2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       neddle
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2040
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0499
_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)+(0.0598P)²+0.6163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1193
_refine_ls_wR_factor_ref         0.1290
_reflns_number_gt                1574
_reflns_number_total             2040
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc30712j.txt
_cod_data_source_block           jh1
_cod_original_cell_volume        927.3(7)
_cod_original_sg_symbol_H-M      P2(1)/m(11)
_cod_database_code               7107582
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -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
N1 N 0.5396(2) 0.2500 0.70498(17) 0.0320(6) Uani 1 2 d S
C1 C 0.4423(3) 0.2500 0.6126(2) 0.0316(6) Uani 1 2 d S
Cl1 Cl 0.28633(8) 0.2500 0.62593(6) 0.0744(4) Uani 1 2 d S
C2 C 0.4625(2) 0.2500 0.5114(2) 0.0245(6) Uani 1 2 d S
N2 N 0.5898(2) 0.2500 0.51432(17) 0.0292(5) Uani 1 2 d S
C3 C 0.6890(3) 0.2500 0.6075(2) 0.0278(6) Uani 1 2 d S
C4 C 0.6647(2) 0.2500 0.7039(2) 0.0262(6) Uani 1 2 d S
C5 C 0.7727(3) 0.2500 0.8059(2) 0.0302(6) Uani 1 2 d S
N3 N 0.8582(2) 0.2500 0.88505(18) 0.0377(6) Uani 1 2 d S
C6 C 0.8220(3) 0.2500 0.6005(2) 0.0343(7) Uani 1 2 d S
N4 N 0.9269(3) 0.2500 0.5950(2) 0.0456(7) Uani 1 2 d S
C7 C 0.3637(2) 0.2500 0.4020(2) 0.0244(6) Uani 1 2 d S
C8 C 0.2251(3) 0.2500 0.3758(2) 0.0269(6) Uani 1 2 d S
H8 H 0.1891 0.2500 0.4308 0.032 Uiso 1 2 calc SR
C9 C 0.1390(2) 0.2500 0.2709(2) 0.0262(6) Uani 1 2 d S
C10 C 0.1960(3) 0.2500 0.1884(2) 0.0274(6) Uani 1 2 d S
O1 O 0.12235(18) 0.2500 0.08337(15) 0.0358(5) Uani 1 2 d SD
H1 H 0.043(2) 0.2500 0.078(3) 0.054 Uiso 1 2 d SD
C11 C 0.3363(2) 0.2500 0.2110(2) 0.0247(6) Uani 1 2 d S
C12 C 0.4152(2) 0.2500 0.3172(2) 0.0249(6) Uani 1 2 d S
H12 H 0.5072 0.2500 0.3336 0.030 Uiso 1 2 calc SR
C13 C -0.0143(2) 0.2500 0.2463(2) 0.0310(7) Uani 1 2 d S
C14 C -0.0498(3) 0.2500 0.3497(2) 0.0370(7) Uani 1 2 d S
H14A H -0.1449 0.2500 0.3321 0.055 Uiso 1 2 calc SR
H14B H -0.0133 0.3625 0.3908 0.055 Uiso 0.50 1 calc PR
H14C H -0.0133 0.1375 0.3908 0.055 Uiso 0.50 1 calc PR
C15 C -0.07708(18) 0.0682(4) 0.18427(16) 0.0394(5) Uani 1 1 d .
H15A H -0.1716 0.0701 0.1702 0.059 Uiso 1 1 calc R
H15B H -0.0394 -0.0431 0.2260 0.059 Uiso 1 1 calc R
H15C H -0.0594 0.0640 0.1179 0.059 Uiso 1 1 calc R
C16 C 0.3993(2) 0.2500 0.1219(2) 0.0287(6) Uani 1 2 d S
C17 C 0.3583(2) 0.0691(4) 0.05272(16) 0.0421(6) Uani 1 1 d .
H17A H 0.3911 0.0770 -0.0064 0.063 Uiso 1 1 calc R
H17B H 0.2629 0.0591 0.0263 0.063 Uiso 1 1 calc R
H17C H 0.3953 -0.0420 0.0950 0.063 Uiso 1 1 calc R
C18 C 0.5522(3) 0.2500 0.1673(2) 0.0343(7) Uani 1 2 d S
H18A H 0.5822 0.3613 0.2114 0.052 Uiso 0.50 1 calc PR
H18B H 0.5877 0.2523 0.1096 0.052 Uiso 1 2 calc SR
H18C H 0.5823 0.1364 0.2094 0.052 Uiso 0.50 1 calc PR
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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C4 117.9(2) . .
N1 C1 C2 124.0(2) . .
N1 C1 Cl1 113.0(2) . .
C2 C1 Cl1 123.1(2) . .
N2 C2 C1 116.0(2) . .
N2 C2 C7 114.1(2) . .
C1 C2 C7 129.9(2) . .
C3 N2 C2 120.5(2) . .
N2 C3 C4 121.5(2) . .
N2 C3 C6 115.5(2) . .
C4 C3 C6 123.0(2) . .
N1 C4 C3 120.1(2) . .
N1 C4 C5 118.2(2) . .
C3 C4 C5 121.7(2) . .
N3 C5 C4 179.2(3) . .
N4 C6 C3 180.0(3) . .
C8 C7 C12 117.4(2) . .
C8 C7 C2 126.2(2) . .
C12 C7 C2 116.4(2) . .
C9 C8 C7 122.6(2) . .
C8 C9 C10 117.7(2) . .
C8 C9 C13 120.4(2) . .
C10 C9 C13 121.8(2) . .
O1 C10 C9 123.1(2) . .
O1 C10 C11 115.2(2) . .
C9 C10 C11 121.7(2) . .
C12 C11 C10 117.1(2) . .
C12 C11 C16 120.8(2) . .
C10 C11 C16 122.1(2) . .
C11 C12 C7 123.4(2) . .
C15 C13 C15 111.0(2) 4_565 .
C15 C13 C14 106.60(15) 4_565 .
C15 C13 C14 106.60(15) . .
C15 C13 C9 110.55(14) 4_565 .
C15 C13 C9 110.55(14) . .
C14 C13 C9 111.4(2) . .
C17 C16 C17 110.5(2) . 4_565
C17 C16 C18 106.74(15) . .
C17 C16 C18 106.75(15) 4_565 .
C17 C16 C11 110.44(14) . .
C17 C16 C11 110.44(14) 4_565 .
C18 C16 C11 111.9(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.315(3) .
N1 C4 1.336(3) .
C1 C2 1.427(4) .
C1 Cl1 1.727(3) .
C2 N2 1.342(3) .
C2 C7 1.482(3) .
N2 C3 1.332(3) .
C3 C4 1.385(4) .
C3 C6 1.449(4) .
C4 C5 1.455(4) .
C5 N3 1.138(3) .
C6 N4 1.142(4) .
C7 C8 1.398(4) .
C7 C12 1.405(4) .
C8 C9 1.389(4) .
C9 C10 1.415(4) .
C9 C13 1.554(4) .
C10 O1 1.353(3) .
C10 C11 1.422(4) .
C11 C12 1.379(4) .
C11 C16 1.540(4) .
C13 C15 1.537(3) 4_565
C13 C15 1.537(3) .
C13 C14 1.538(4) .
C16 C17 1.535(3) .
C16 C17 1.535(3) 4_565
C16 C18 1.536(4) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N3 0.825(18) 2.66(3) 3.147(3) 119(3) 1_454
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_4
C4 N1 C1 C2 0.000(1) .
C4 N1 C1 Cl1 180.0 .
N1 C1 C2 N2 0.000(1) .
Cl1 C1 C2 N2 180.0 .
N1 C1 C2 C7 180.0 .
Cl1 C1 C2 C7 0.000(1) .
C1 C2 N2 C3 0.0 .
C7 C2 N2 C3 180.0 .
C2 N2 C3 C4 0.000(1) .
C2 N2 C3 C6 180.0 .
C1 N1 C4 C3 0.000(1) .
C1 N1 C4 C5 180.0 .
N2 C3 C4 N1 0.000(1) .
C6 C3 C4 N1 180.0 .
N2 C3 C4 C5 180.000(1) .
C6 C3 C4 C5 0.000(1) .
N1 C4 C5 N3 180.00(8) .
C3 C4 C5 N3 0.00(8) .
N2 C3 C6 N4 180(100) .
C4 C3 C6 N4 0(100) .
N2 C2 C7 C8 180.0 .
C1 C2 C7 C8 0.0 .
N2 C2 C7 C12 0.0 .
C1 C2 C7 C12 180.0 .
C12 C7 C8 C9 0.0 .
C2 C7 C8 C9 180.0 .
C7 C8 C9 C10 0.0 .
C7 C8 C9 C13 180.0 .
C8 C9 C10 O1 180.0 .
C13 C9 C10 O1 0.0 .
C8 C9 C10 C11 0.0 .
C13 C9 C10 C11 180.0 .
O1 C10 C11 C12 180.0 .
C9 C10 C11 C12 0.0 .
O1 C10 C11 C16 0.0 .
C9 C10 C11 C16 180.0 .
C10 C11 C12 C7 0.0 .
C16 C11 C12 C7 180.0 .
C8 C7 C12 C11 0.0 .
C2 C7 C12 C11 180.0 .
C8 C9 C13 C15 118.33(15) 4_565
C10 C9 C13 C15 -61.67(15) 4_565
C8 C9 C13 C15 -118.33(15) .
C10 C9 C13 C15 61.67(15) .
C8 C9 C13 C14 0.0 .
C10 C9 C13 C14 180.0 .
C12 C11 C16 C17 118.76(16) .
C10 C11 C16 C17 -61.24(16) .
C12 C11 C16 C17 -118.76(16) 4_565
C10 C11 C16 C17 61.24(16) 4_565
C12 C11 C16 C18 0.0 .
C10 C11 C16 C18 180.0 .
