#------------------------------------------------------------------------------
#$Date: 2016-04-05 17:53:08 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181562 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/88/7118818.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_7118818
loop_
_publ_author_name
'Grzybowski, Marek'
'Deperasińska, Irena'
'Chotkowski, Maciej'
'Banasiewicz, Marzena'
'Makarewicz, Artur'
'Kozankiewicz, Bolesław'
'Gryko, Daniel T.'
_publ_section_title
;
 Dipyrrolonaphthyridinediones - structurally unique cross-conjugated dyes.
;
_journal_issue                   29
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              5108
_journal_page_last               5111
_journal_paper_doi               10.1039/c6cc01017b
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.33
_chemical_name_systematic
;
 dipyrrolo[1,2-b:1 ,2 -g][2,6]naphthyridine-5,11-dione
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_Hall           '-I 4ad'
_space_group_name_H-M_alt        'I 41/a'
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2016-02-02 deposited with the CCDC.
2016-03-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.3920(10)
_cell_length_b                   24.3920(10)
_cell_length_c                   4.8236(3)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      3.62
_cell_volume                     2869.9(2)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.879
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_Laue_measured_fraction_full 0.879
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            7619
_diffrn_reflns_point_group_measured_fraction_full 0.879
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.298
_diffrn_reflns_theta_min         3.624
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.720
_exptl_absorpt_correction_T_max  0.9420
_exptl_absorpt_correction_T_min  0.7932
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1232
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: 1,2-dichloroethane/methanol'
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.084
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1156
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0401
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0547P)²+0.3487P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                886
_reflns_number_total             1156
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc01017b2.cif
_cod_data_source_block           MGG492_0ma
_cod_depositor_comments          'Adding full bibliography for 7118818.cif.'
_cod_original_cell_volume        2869.9(3)
_cod_database_code               7118818
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.793
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.57847(6) 0.59543(5) 0.0536(3) 0.0744(5) Uani 1 1 d . .
N1 N 0.58486(6) 0.51559(6) 0.2808(3) 0.0559(4) Uani 1 1 d . .
C1 C 0.63138(9) 0.52824(10) 0.4301(5) 0.0746(6) Uani 1 1 d . .
H1 H 0.6510 0.5609 0.4208 0.090 Uiso 1 1 calc R U
C2 C 0.64340(11) 0.48453(11) 0.5929(5) 0.0860(8) Uani 1 1 d . .
H2 H 0.6729 0.4819 0.7143 0.103 Uiso 1 1 calc R U
C3 C 0.60364(10) 0.44381(10) 0.5466(4) 0.0743(6) Uani 1 1 d . .
H3 H 0.6023 0.4096 0.6318 0.089 Uiso 1 1 calc R U
C4 C 0.56704(8) 0.46342(7) 0.3530(3) 0.0544(5) Uani 1 1 d . .
C5 C 0.51889(8) 0.44133(6) 0.2293(3) 0.0500(4) Uani 1 1 d . .
C6 C 0.49063(7) 0.47231(6) 0.0387(3) 0.0455(4) Uani 1 1 d . .
C7 C 0.55889(7) 0.55021(7) 0.0923(4) 0.0524(4) Uani 1 1 d . .
C8 C 0.50385(10) 0.38420(7) 0.3234(4) 0.0635(5) Uani 1 1 d . .
H8A H 0.4643 0.3815 0.3386 0.076 Uiso 1 1 calc R U
H8B H 0.5193 0.3778 0.5058 0.076 Uiso 1 1 calc R U
C9 C 0.52442(9) 0.34010(7) 0.1252(4) 0.0684(6) Uani 1 1 d . .
H9A H 0.5060 0.3437 -0.0498 0.103 Uiso 1 1 calc R U
H9B H 0.5170 0.3046 0.2020 0.103 Uiso 1 1 calc R U
H9C H 0.5632 0.3443 0.0986 0.103 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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 109.37(17) . .
C1 N1 C7 125.41(17) . .
C4 N1 C7 125.20(15) . .
C2 C1 N1 107.7(2) . .
C2 C1 H1 126.1 . .
N1 C1 H1 126.1 . .
C1 C2 C3 108.3(2) . .
C1 C2 H2 125.8 . .
C3 C2 H2 125.8 . .
C4 C3 C2 108.0(2) . .
C4 C3 H3 126.0 . .
C2 C3 H3 126.0 . .
C3 C4 N1 106.57(18) . .
C3 C4 C5 133.43(19) . .
N1 C4 C5 120.00(15) . .
C6 C5 C4 119.07(15) . .
C6 C5 C8 125.85(18) . .
C4 C5 C8 115.07(16) . .
C5 C6 C7 119.60(15) . 9_665
C5 C6 C6 121.1(2) . 9_665
C7 C6 C6 119.26(19) 9_665 9_665
O1 C7 N1 118.10(17) . .
O1 C7 C6 126.57(18) . 9_665
N1 C7 C6 115.33(15) . 9_665
C5 C8 C9 112.51(15) . .
C5 C8 H8A 109.1 . .
C9 C8 H8A 109.1 . .
C5 C8 H8B 109.1 . .
C9 C8 H8B 109.1 . .
H8A C8 H8B 107.8 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.217(2) .
N1 C1 1.379(3) .
N1 C4 1.389(3) .
N1 C7 1.393(2) .
C1 C2 1.356(4) .
C1 H1 0.9300 .
C2 C3 1.406(4) .
C2 H2 0.9300 .
C3 C4 1.377(3) .
C3 H3 0.9300 .
C4 C5 1.423(3) .
C5 C6 1.375(2) .
C5 C8 1.511(2) .
C6 C7 1.469(3) 9_665
C6 C6 1.474(3) 9_665
C7 C6 1.469(3) 9_665
C8 C9 1.524(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
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
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
C3 H3 O1 0.93 2.50 3.316(3) 147.1 2_645
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 0.7(2) .
C7 N1 C1 C2 179.11(18) .
N1 C1 C2 C3 -0.3(3) .
C1 C2 C3 C4 -0.1(3) .
C2 C3 C4 N1 0.5(2) .
C2 C3 C4 C5 -179.14(19) .
C1 N1 C4 C3 -0.70(19) .
C7 N1 C4 C3 -179.16(15) .
C1 N1 C4 C5 178.99(15) .
C7 N1 C4 C5 0.5(2) .
C3 C4 C5 C6 179.64(18) .
N1 C4 C5 C6 0.1(2) .
C3 C4 C5 C8 -0.7(3) .
N1 C4 C5 C8 179.70(15) .
C4 C5 C6 C7 179.49(13) 9_665
C8 C5 C6 C7 -0.1(2) 9_665
C4 C5 C6 C6 -0.1(3) 9_665
C8 C5 C6 C6 -179.66(17) 9_665
C1 N1 C7 O1 0.2(3) .
C4 N1 C7 O1 178.38(16) .
C1 N1 C7 C6 -179.21(15) 9_665
C4 N1 C7 C6 -1.0(2) 9_665
C6 C5 C8 C9 83.0(2) .
C4 C5 C8 C9 -96.6(2) .
