#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:10:37 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180291 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/05/7150515.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_7150515
loop_
_publ_author_name
'Boeyens, Jan C. A.'
'Cook, Leanne M.'
'Ding, Yunxiang'
'Fernandes, Manuel A.'
'Reid, David H.'
_publ_section_title
;
 Thermal oligomerisation of aryl isocyanides: formation of
 pyrazino[1,2-a:4,5-a?]diindoles and indigo diarylimines
;
_journal_issue                   12
_journal_name_full               'Organic &  Biomolecular Chemistry'
_journal_page_first              2168
_journal_paper_doi               10.1039/b302340k
_journal_volume                  1
_journal_year                    2003
_chemical_formula_moiety         'C42 H24 F6 N6, 2(C3 H7 N O)'
_chemical_formula_sum            'C48 H38 F6 N8 O2'
_chemical_formula_weight         872.86
_chemical_name_common
;
7,14-di-(4-fluorophenylamino)-6,13-di-(4-fluorophenylimino)pyrazino
[1,2-a:4,5-a']diindole 
;
_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                109.812(2)
_cell_angle_beta                 93.863(2)
_cell_angle_gamma                95.079(3)
_cell_formula_units_Z            1
_cell_length_a                   7.9770(11)
_cell_length_b                   10.8182(15)
_cell_length_c                   13.3466(19)
_cell_measurement_temperature    293(2)
_cell_volume                     1073.5(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7601
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.9918
_exptl_absorpt_correction_T_min  0.9668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plates
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5195
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.1095
_refine_ls_R_factor_gt           0.0505
_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)+(0.0720P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1478
_reflns_number_gt                2792
_reflns_number_total             5195
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b302340k.txt
_cod_data_source_block           2mrd4_s
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/adriana/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed
to 'multi-scan' according to
'/home/adriana/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7150515
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.5890(2) 0.94551(16) 0.41209(14) 0.0329(4) Uani 1 1 d . . .
C3 C 0.7188(2) 0.91337(16) 0.34848(14) 0.0326(4) Uani 1 1 d . . .
C4 C 0.9996(2) 0.81895(17) 0.37988(16) 0.0405(5) Uani 1 1 d . . .
H4 H 1.0419 0.8140 0.3155 0.049 Uiso 1 1 calc R . .
C5 C 1.0872(2) 0.78283(18) 0.45474(17) 0.0440(5) Uani 1 1 d . . .
C6 C 1.0318(2) 0.78950(18) 0.55199(16) 0.0446(5) Uani 1 1 d . . .
H6 H 1.0965 0.7619 0.5993 0.054 Uiso 1 1 calc R . .
C7 C 0.8803(2) 0.83715(17) 0.57866(15) 0.0410(5) Uani 1 1 d . . .
H7 H 0.8420 0.8444 0.6445 0.049 Uiso 1 1 calc R . .
C8 C 0.7948(2) 0.85918(18) 0.16224(15) 0.0386(4) Uani 1 1 d . . .
C9 C 0.8337(3) 0.9123(2) 0.08432(17) 0.0557(6) Uani 1 1 d . . .
H9 H 0.8235 1.0009 0.0960 0.067 Uiso 1 1 calc R . .
C10 C 0.8874(3) 0.8347(3) -0.01030(19) 0.0725(7) Uani 1 1 d . . .
H10 H 0.9109 0.8699 -0.0631 0.087 Uiso 1 1 calc R . .
C11 C 0.9055(3) 0.7055(3) -0.0253(2) 0.0694(7) Uani 1 1 d . . .
C12 C 0.8674(3) 0.6500(2) 0.04959(18) 0.0586(6) Uani 1 1 d . . .
H12 H 0.8799 0.5616 0.0375 0.070 Uiso 1 1 calc R . .
C13 C 0.8106(2) 0.72648(19) 0.14283(16) 0.0454(5) Uani 1 1 d . . .
H13 H 0.7823 0.6890 0.1936 0.055 Uiso 1 1 calc R . .
C14 C 0.5675(2) 1.00101(16) 0.60608(14) 0.0336(4) Uani 1 1 d . . .
C15 C 0.6309(2) 1.10945(18) 0.79349(14) 0.0384(4) Uani 1 1 d . . .
C16 C 0.6296(2) 1.24204(18) 0.80407(15) 0.0444(5) Uani 1 1 d . . .
H16 H 0.6356 1.2670 0.7441 0.053 Uiso 1 1 calc R . .
C17 C 0.6196(3) 1.3367(2) 0.90294(17) 0.0521(5) Uani 1 1 d . . .
H17 H 0.6180 1.4251 0.9100 0.063 Uiso 1 1 calc R . .
C18 C 0.6121(3) 1.2984(2) 0.98960(16) 0.0552(6) Uani 1 1 d . . .
C19 C 0.6192(3) 1.1701(2) 0.98357(17) 0.0568(6) Uani 1 1 d . . .
H19 H 0.6168 1.1470 1.0446 0.068 Uiso 1 1 calc R . .
C20 C 0.6301(3) 1.0761(2) 0.88485(16) 0.0488(5) Uani 1 1 d . . .
H20 H 0.6369 0.9888 0.8796 0.059 Uiso 1 1 calc R . .
C21 C 0.5603(4) 0.2855(3) 0.2900(2) 0.0879(9) Uani 1 1 d . . .
H21 H 0.4480 0.2490 0.2818 0.105 Uiso 1 1 calc R . .
C22 C 0.4634(9) 0.5004(5) 0.3486(4) 0.252(4) Uani 1 1 d . . .
H22A H 0.3533 0.4520 0.3223 0.378 Uiso 1 1 calc R . .
H22B H 0.4849 0.5635 0.3135 0.378 Uiso 1 1 calc R . .
H22C H 0.4681 0.5459 0.4244 0.378 Uiso 1 1 calc R . .
C23 C 0.7583(7) 0.4753(4) 0.3393(4) 0.181(2) Uani 1 1 d . . .
H23A H 0.8045 0.5028 0.4128 0.271 Uiso 1 1 calc R . .
H23B H 0.7590 0.5511 0.3172 0.271 Uiso 1 1 calc R . .
H23C H 0.8255 0.4132 0.2954 0.271 Uiso 1 1 calc R . .
C3A C 0.8425(2) 0.86403(16) 0.40456(14) 0.0335(4) Uani 1 1 d . . .
C7A C 0.7865(2) 0.87410(16) 0.50417(14) 0.0344(4) Uani 1 1 d . . .
F1 F 1.24123(14) 0.73904(12) 0.43384(10) 0.0651(4) Uani 1 1 d . . .
F2 F 0.9591(2) 0.62898(17) -0.11928(13) 0.1153(6) Uani 1 1 d . . .
F3 F 0.5998(2) 1.39184(13) 1.08701(10) 0.0844(5) Uani 1 1 d . . .
N1 N 0.63189(17) 0.92761(13) 0.51076(11) 0.0347(4) Uani 1 1 d . . .
N2 N 0.73505(19) 0.93997(14) 0.25538(12) 0.0383(4) Uani 1 1 d . . .
H2 H 0.7053 1.0141 0.2545 0.046 Uiso 1 1 calc R . .
N3 N 0.65149(19) 1.01211(15) 0.69454(12) 0.0400(4) Uani 1 1 d . . .
N4 N 0.5851(4) 0.4131(2) 0.32783(18) 0.0912(8) Uani 1 1 d . . .
O1 O 0.6602(2) 0.20715(15) 0.26391(14) 0.0746(5) 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'
F F 0.0171 0.0103 '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
_geom_angle_publ_flag
C3 C2 N1 109.18(14) . . ?
C3 C2 C14 130.10(16) . 2_676 ?
N1 C2 C14 120.59(14) . 2_676 ?
C2 C3 N2 125.33(15) . . ?
C2 C3 C3A 107.26(15) . . ?
N2 C3 C3A 126.94(15) . . ?
C5 C4 C3A 116.81(18) . . ?
C5 C4 H4 121.6 . . ?
C3A C4 H4 121.6 . . ?
C4 C5 F1 118.53(18) . . ?
C4 C5 C6 124.15(17) . . ?
F1 C5 C6 117.31(17) . . ?
C7 C6 C5 119.71(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C7A 117.93(18) . . ?
C6 C7 H7 121.0 . . ?
C7A C7 H7 121.0 . . ?
C9 C8 C13 118.66(18) . . ?
C9 C8 N2 118.73(17) . . ?
C13 C8 N2 122.56(17) . . ?
C10 C9 C8 120.6(2) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 F2 118.9(2) . . ?
C12 C11 F2 119.3(2) . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
N3 C14 N1 117.23(15) . . ?
N3 C14 C2 129.31(16) . 2_676 ?
N1 C14 C2 113.46(15) . 2_676 ?
C20 C15 C16 118.45(17) . . ?
C20 C15 N3 119.64(16) . . ?
C16 C15 N3 121.54(17) . . ?
C17 C16 C15 120.53(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 118.83(19) . . ?
C18 C17 H17 120.6 . . ?
C16 C17 H17 120.6 . . ?
C17 C18 F3 118.7(2) . . ?
C17 C18 C19 122.60(19) . . ?
F3 C18 C19 118.6(2) . . ?
C18 C19 C20 118.35(19) . . ?
C18 C19 H19 120.8 . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C15 121.13(19) . . ?
C19 C20 H20 119.4 . . ?
C15 C20 H20 119.4 . . ?
O1 C21 N4 129.6(3) . . ?
O1 C21 H21 115.2 . . ?
N4 C21 H21 115.2 . . ?
N4 C22 H22A 109.5 . . ?
N4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N4 C23 H23A 109.5 . . ?
N4 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N4 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C7A C3A C4 119.56(16) . . ?
C7A C3A C3 107.60(14) . . ?
C4 C3A C3 132.73(17) . . ?
C7 C7A C3A 121.79(16) . . ?
C7 C7A N1 130.02(16) . . ?
C3A C7A N1 108.18(15) . . ?
C7A N1 C14 125.63(15) . . ?
C7A N1 C2 107.59(13) . . ?
C14 N1 C2 121.96(14) . . ?
C3 N2 C8 126.90(15) . . ?
C3 N2 H2 116.6 . . ?
C8 N2 H2 116.6 . . ?
C14 N3 C15 123.30(15) . . ?
C21 N4 C22 127.5(4) . . ?
C21 N4 C23 117.4(3) . . ?
C22 N4 C23 114.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C2 C3 1.376(2) . ?
C2 N1 1.419(2) . ?
C2 C14 1.462(2) 2_676 ?
C3 N2 1.379(2) . ?
C3 C3A 1.443(2) . ?
C4 C5 1.363(3) . ?
C4 C3A 1.405(2) . ?
C4 H4 0.9300 . ?
C5 F1 1.368(2) . ?
C5 C6 1.380(3) . ?
C6 C7 1.377(2) . ?
C6 H6 0.9300 . ?
C7 C7A 1.389(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C8 C13 1.389(2) . ?
C8 N2 1.398(2) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.365(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(3) . ?
C11 F2 1.368(2) . ?
C12 C13 1.372(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 N3 1.281(2) . ?
C14 N1 1.410(2) . ?
C14 C2 1.462(2) 2_676 ?
C15 C20 1.384(3) . ?
C15 C16 1.394(2) . ?
C15 N3 1.413(2) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 F3 1.366(2) . ?
C18 C19 1.369(3) . ?
C19 C20 1.378(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 O1 1.197(3) . ?
C21 N4 1.290(3) . ?
C21 H21 0.9300 . ?
C22 N4 1.390(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 N4 1.457(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C3A C7A 1.403(2) . ?
C7A N1 1.403(2) . ?
N2 H2 0.8600 . ?
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -168.20(15) . . . . ?
C14 C2 C3 N2 7.7(3) 2_676 . . . ?
N1 C2 C3 C3A 4.35(19) . . . . ?
C14 C2 C3 C3A -179.77(16) 2_676 . . . ?
C3A C4 C5 F1 -179.66(15) . . . . ?
C3A C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
F1 C5 C6 C7 177.80(16) . . . . ?
C5 C6 C7 C7A 1.5(3) . . . . ?
C13 C8 C9 C10 -0.2(3) . . . . ?
N2 C8 C9 C10 -177.8(2) . . . . ?
C8 C9 C10 C11 -1.5(4) . . . . ?
C9 C10 C11 C12 1.8(4) . . . . ?
C9 C10 C11 F2 -179.9(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
F2 C11 C12 C13 -178.7(2) . . . . ?
C11 C12 C13 C8 -1.2(3) . . . . ?
C9 C8 C13 C12 1.5(3) . . . . ?
N2 C8 C13 C12 179.04(18) . . . . ?
C20 C15 C16 C17 -3.0(3) . . . . ?
N3 C15 C16 C17 -176.08(17) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 F3 -179.09(19) . . . . ?
C16 C17 C18 C19 2.0(3) . . . . ?
C17 C18 C19 C20 -1.7(4) . . . . ?
F3 C18 C19 C20 179.40(19) . . . . ?
C18 C19 C20 C15 -1.1(3) . . . . ?
C16 C15 C20 C19 3.4(3) . . . . ?
N3 C15 C20 C19 176.54(19) . . . . ?
C5 C4 C3A C7A 2.2(3) . . . . ?
C5 C4 C3A C3 177.88(17) . . . . ?
C2 C3 C3A C7A -2.84(19) . . . . ?
N2 C3 C3A C7A 169.55(16) . . . . ?
C2 C3 C3A C4 -178.93(18) . . . . ?
N2 C3 C3A C4 -6.5(3) . . . . ?
C6 C7 C7A C3A -0.1(3) . . . . ?
C6 C7 C7A N1 -178.50(17) . . . . ?
C4 C3A C7A C7 -1.8(3) . . . . ?
C3 C3A C7A C7 -178.50(16) . . . . ?
C4 C3A C7A N1 176.93(15) . . . . ?
C3 C3A C7A N1 0.23(19) . . . . ?
C7 C7A N1 C14 25.4(3) . . . . ?
C3A C7A N1 C14 -153.17(16) . . . . ?
C7 C7A N1 C2 -179.02(17) . . . . ?
C3A C7A N1 C2 2.40(18) . . . . ?
N3 C14 N1 C7A -5.1(3) . . . . ?
C2 C14 N1 C7A 174.69(15) 2_676 . . . ?
N3 C14 N1 C2 -157.44(16) . . . . ?
C2 C14 N1 C2 22.4(2) 2_676 . . . ?
C3 C2 N1 C7A -4.26(19) . . . . ?
C14 C2 N1 C7A 179.41(15) 2_676 . . . ?
C3 C2 N1 C14 152.40(16) . . . . ?
C14 C2 N1 C14 -23.9(3) 2_676 . . . ?
C2 C3 N2 C8 -142.45(18) . . . . ?
C3A C3 N2 C8 46.5(3) . . . . ?
C9 C8 N2 C3 -167.51(18) . . . . ?
C13 C8 N2 C3 15.0(3) . . . . ?
N1 C14 N3 C15 162.17(16) . . . . ?
C2 C14 N3 C15 -17.6(3) 2_676 . . . ?
C20 C15 N3 C14 139.0(2) . . . . ?
C16 C15 N3 C14 -48.0(3) . . . . ?
O1 C21 N4 C22 174.1(4) . . . . ?
O1 C21 N4 C23 1.8(5) . . . . ?
