#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:55:11 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180455 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/24/7212414.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_7212414
loop_
_publ_author_name
'Pogozhev, Dmitry'
'Baudron, Stéphane A.'
'Hosseini, Mir Wais'
_publ_section_title
;
 Combination of hydrogen and coordination bonding for the construction of
 one-dimensional networks based on a 7-azaindole appended dipyrrin
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              2238
_journal_paper_doi               10.1039/b927348d
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C22 H18 N4, C4 H8 O2 '
_chemical_formula_sum            'C26 H26 N4 O2'
_chemical_formula_weight         426.51
_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                100.454(2)
_cell_angle_beta                 97.8740(10)
_cell_angle_gamma                109.0960(10)
_cell_formula_units_Z            2
_cell_length_a                   8.5597(3)
_cell_length_b                   9.3106(2)
_cell_length_c                   15.2765(4)
_cell_measurement_reflns_used    3045
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.83
_cell_measurement_theta_min      2.58
_cell_volume                     1105.84(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0418
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12267
_diffrn_reflns_theta_full        27.69
_diffrn_reflns_theta_max         27.69
_diffrn_reflns_theta_min         1.39
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0566
_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)+(0.0758P)²+0.6481P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1521
_refine_ls_wR_factor_ref         0.1695
_reflns_number_gt                3644
_reflns_number_total             5012
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b927348d.txt
_cod_data_source_block           compound4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1105.84(5)
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7212414
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
C1 C 0.6547(3) 0.0939(3) 0.21998(16) 0.0329(5) Uani 1 1 d .
H1A H 0.7253 0.0375 0.2274 0.040 Uiso 1 1 calc R
C2 C 0.6233(3) 0.1514(3) 0.14643(16) 0.0340(5) Uani 1 1 d .
H2A H 0.6673 0.1406 0.0943 0.041 Uiso 1 1 calc R
C3 C 0.5102(3) 0.2310(3) 0.16429(15) 0.0302(5) Uani 1 1 d .
H3A H 0.4673 0.2823 0.1259 0.036 Uiso 1 1 calc R
C4 C 0.4764(2) 0.2183(2) 0.24784(14) 0.0241(4) Uani 1 1 d .
C5 C 0.3732(3) 0.2871(2) 0.30316(14) 0.0247(4) Uani 1 1 d .
H5 H 0.4497 0.3548 0.3602 0.030 Uiso 1 1 calc R
C6 C 0.2330(3) 0.1646(2) 0.32794(13) 0.0255(4) Uani 1 1 d .
C7 C 0.1581(3) 0.0068(2) 0.29357(15) 0.0310(5) Uani 1 1 d .
H7 H 0.1900 -0.0538 0.2492 0.037 Uiso 1 1 calc R
C8 C 0.0226(3) -0.0485(3) 0.33771(17) 0.0387(5) Uani 1 1 d .
H8 H -0.0502 -0.1517 0.3277 0.046 Uiso 1 1 calc R
C9 C 0.0191(3) 0.0773(3) 0.39722(17) 0.0371(5) Uani 1 1 d .
H9 H -0.0575 0.0756 0.4351 0.045 Uiso 1 1 calc R
C10 C 0.3077(3) 0.3909(2) 0.25359(13) 0.0247(4) Uani 1 1 d .
C11 C 0.4041(3) 0.5481(2) 0.26709(14) 0.0274(4) Uani 1 1 d .
H11 H 0.5090 0.5901 0.3071 0.033 Uiso 1 1 calc R
C12 C 0.3469(3) 0.6442(2) 0.22190(14) 0.0267(4) Uani 1 1 d .
H12 H 0.4135 0.7496 0.2325 0.032 Uiso 1 1 calc R
C13 C 0.1910(2) 0.5845(2) 0.16087(13) 0.0234(4) Uani 1 1 d .
C14 C 0.0954(3) 0.4257(2) 0.14709(14) 0.0278(4) Uani 1 1 d .
H14 H -0.0088 0.3830 0.1065 0.033 Uiso 1 1 calc R
C15 C 0.1520(3) 0.3305(2) 0.19236(14) 0.0291(5) Uani 1 1 d .
H15 H 0.0856 0.2251 0.1819 0.035 Uiso 1 1 calc R
C16 C 0.2199(3) 0.8130(2) 0.08600(14) 0.0253(4) Uani 1 1 d .
H16 H 0.3356 0.8441 0.0882 0.030 Uiso 1 1 calc R
C17 C 0.1272(2) 0.6867(2) 0.11524(13) 0.0239(4) Uani 1 1 d .
C18 C -0.0437(2) 0.6826(2) 0.09963(13) 0.0227(4) Uani 1 1 d .
C19 C -0.1972(3) 0.5926(2) 0.11610(14) 0.0291(5) Uani 1 1 d .
H19 H -0.2063 0.5074 0.1415 0.035 Uiso 1 1 calc R
C20 C -0.3357(3) 0.6344(3) 0.09340(15) 0.0316(5) Uani 1 1 d .
H20 H -0.4403 0.5768 0.1033 0.038 Uiso 1 1 calc R
C21 C -0.3181(3) 0.7630(3) 0.05564(14) 0.0304(5) Uani 1 1 d .
H21 H -0.4140 0.7874 0.0410 0.037 Uiso 1 1 calc R
C22 C -0.0424(2) 0.8112(2) 0.06153(13) 0.0229(4) Uani 1 1 d .
N1 N 0.5645(2) 0.1337(2) 0.28100(12) 0.0295(4) Uani 1 1 d .
H1 H 0.5632 0.1093 0.3326 0.035 Uiso 1 1 calc R
N2 N 0.1475(2) 0.2065(2) 0.39170(13) 0.0331(4) Uani 1 1 d .
H2 H 0.1712 0.3001 0.4234 0.040 Uiso 1 1 calc R
N3 N 0.1179(2) 0.88727(19) 0.05298(12) 0.0258(4) Uani 1 1 d .
H3 H 0.1501 0.9680 0.0307 0.031 Uiso 1 1 calc R
N4 N -0.1745(2) 0.8534(2) 0.03893(12) 0.0269(4) Uani 1 1 d .
C23 C 0.6053(3) -0.0678(3) 0.46175(17) 0.0385(5) Uani 1 1 d .
H23A H 0.6766 -0.0721 0.5156 0.046 Uiso 1 1 calc R
H23B H 0.6382 -0.1143 0.4086 0.046 Uiso 1 1 calc R
C24 C 0.5762(3) 0.1585(3) 0.54022(17) 0.0430(6) Uani 1 1 d .
H24A H 0.5903 0.2663 0.5404 0.052 Uiso 1 1 calc R
H24B H 0.6468 0.1585 0.5956 0.052 Uiso 1 1 calc R
O1 O 0.6286(2) 0.0912(2) 0.46265(11) 0.0381(4) Uani 1 1 d .
C25 C 0.1227(4) 0.5363(4) 0.5765(2) 0.0615(8) Uani 1 1 d .
H25A H 0.1449 0.6468 0.5996 0.074 Uiso 1 1 calc R
H25B H 0.1950 0.5057 0.6181 0.074 Uiso 1 1 calc R
C26 C 0.0527(4) 0.5528(4) 0.4259(3) 0.0651(9) Uani 1 1 d .
H26A H 0.0757 0.5312 0.3655 0.078 Uiso 1 1 calc R
H26B H 0.0733 0.6639 0.4445 0.078 Uiso 1 1 calc R
O2 O 0.1642(3) 0.5129(2) 0.48863(17) 0.0650(6) 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
C2 C1 N1 107.99(18) . .
C2 C1 H1A 126.0 . .
N1 C1 H1A 126.0 . .
C1 C2 C3 107.13(19) . .
C1 C2 H2A 126.4 . .
C3 C2 H2A 126.4 . .
C4 C3 C2 107.64(18) . .
C4 C3 H3A 126.2 . .
C2 C3 H3A 126.2 . .
C3 C4 N1 107.33(17) . .
C3 C4 C5 130.68(18) . .
N1 C4 C5 121.89(17) . .
C6 C5 C4 112.89(16) . .
C6 C5 C10 112.14(16) . .
C4 C5 C10 109.90(16) . .
C6 C5 H5 107.2 . .
C4 C5 H5 107.2 . .
C10 C5 H5 107.2 . .
C7 C6 N2 107.28(18) . .
C7 C6 C5 131.87(19) . .
N2 C6 C5 120.68(18) . .
C6 C7 C8 107.7(2) . .
C6 C7 H7 126.2 . .
C8 C7 H7 126.2 . .
C9 C8 C7 107.3(2) . .
C9 C8 H8 126.3 . .
C7 C8 H8 126.3 . .
C8 C9 N2 108.0(2) . .
C8 C9 H9 126.0 . .
N2 C9 H9 126.0 . .
C11 C10 C15 118.24(18) . .
C11 C10 C5 120.40(18) . .
C15 C10 C5 121.35(18) . .
C10 C11 C12 121.16(19) . .
C10 C11 H11 119.4 . .
C12 C11 H11 119.4 . .
C11 C12 C13 120.85(18) . .
C11 C12 H12 119.6 . .
C13 C12 H12 119.6 . .
C12 C13 C14 117.59(17) . .
C12 C13 C17 121.09(17) . .
C14 C13 C17 121.28(18) . .
C15 C14 C13 121.52(19) . .
C15 C14 H14 119.2 . .
C13 C14 H14 119.2 . .
C14 C15 C10 120.63(19) . .
C14 C15 H15 119.7 . .
C10 C15 H15 119.7 . .
C17 C16 N3 110.64(17) . .
C17 C16 H16 124.7 . .
N3 C16 H16 124.7 . .
C16 C17 C18 105.94(16) . .
C16 C17 C13 127.40(18) . .
C18 C17 C13 126.45(17) . .
C19 C18 C22 116.88(17) . .
C19 C18 C17 136.48(18) . .
C22 C18 C17 106.56(17) . .
C20 C19 C18 117.67(19) . .
C20 C19 H19 121.2 . .
C18 C19 H19 121.2 . .
C19 C20 C21 119.9(2) . .
C19 C20 H20 120.1 . .
C21 C20 H20 120.1 . .
N4 C21 C20 124.94(18) . .
N4 C21 H21 117.5 . .
C20 C21 H21 117.5 . .
N4 C22 N3 125.06(17) . .
N4 C22 C18 126.47(18) . .
N3 C22 C18 108.47(16) . .
C1 N1 C4 109.91(17) . .
C1 N1 H1 125.0 . .
C4 N1 H1 125.0 . .
C9 N2 C6 109.72(18) . .
C9 N2 H2 125.1 . .
C6 N2 H2 125.1 . .
C22 N3 C16 108.38(16) . .
C22 N3 H3 125.8 . .
C16 N3 H3 125.8 . .
C21 N4 C22 114.13(17) . .
O1 C23 C24 110.27(19) . 2_656
O1 C23 H23A 109.6 . .
C24 C23 H23A 109.6 2_656 .
O1 C23 H23B 109.6 . .
C24 C23 H23B 109.6 2_656 .
H23A C23 H23B 108.1 . .
O1 C24 C23 110.8(2) . 2_656
O1 C24 H24A 109.5 . .
C23 C24 H24A 109.5 2_656 .
O1 C24 H24B 109.5 . .
C23 C24 H24B 109.5 2_656 .
H24A C24 H24B 108.1 . .
C23 O1 C24 109.42(17) . .
O2 C25 C26 112.4(3) . 2_566
O2 C25 H25A 109.1 . .
C26 C25 H25A 109.1 2_566 .
O2 C25 H25B 109.1 . .
C26 C25 H25B 109.1 2_566 .
H25A C25 H25B 107.9 . .
O2 C26 C25 110.7(3) . 2_566
O2 C26 H26A 109.5 . .
C25 C26 H26A 109.5 2_566 .
O2 C26 H26B 109.5 . .
C25 C26 H26B 109.5 2_566 .
H26A C26 H26B 108.1 . .
C25 O2 C26 109.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.360(3) .
C1 N1 1.364(3) .
C1 H1A 0.9300 .
C2 C3 1.424(3) .
C2 H2A 0.9300 .
C3 C4 1.364(3) .
C3 H3A 0.9300 .
C4 N1 1.369(2) .
C4 C5 1.511(3) .
C5 C6 1.506(3) .
C5 C10 1.525(3) .
C5 H5 0.9800 .
C6 C7 1.363(3) .
C6 N2 1.372(3) .
C7 C8 1.419(3) .
C7 H7 0.9300 .
C8 C9 1.357(3) .
C8 H8 0.9300 .
C9 N2 1.364(3) .
C9 H9 0.9300 .
C10 C11 1.385(3) .
C10 C15 1.395(3) .
C11 C12 1.391(3) .
C11 H11 0.9300 .
C12 C13 1.395(3) .
C12 H12 0.9300 .
C13 C14 1.396(3) .
C13 C17 1.471(3) .
C14 C15 1.383(3) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.375(3) .
C16 N3 1.377(2) .
C16 H16 0.9300 .
C17 C18 1.436(3) .
C18 C19 1.392(3) .
C18 C22 1.421(3) .
C19 C20 1.384(3) .
C19 H19 0.9300 .
C20 C21 1.395(3) .
C20 H20 0.9300 .
C21 N4 1.331(3) .
C21 H21 0.9300 .
C22 N4 1.336(2) .
C22 N3 1.360(3) .
N1 H1 0.8600 .
N2 H2 0.8600 .
N3 H3 0.8600 .
C23 O1 1.425(3) .
C23 C24 1.499(3) 2_656
C23 H23A 0.9700 .
C23 H23B 0.9700 .
C24 O1 1.435(3) .
C24 C23 1.499(3) 2_656
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 O2 1.432(4) .
C25 C26 1.450(4) 2_566
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 O2 1.442(4) .
C26 C25 1.450(4) 2_566
C26 H26A 0.9700 .
C26 H26B 0.9700 .
