#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024487.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_4024487
loop_
_publ_author_name
'Pedro Rodriguez-Dafonte'
'François Terrier'
'Sami Lakhdar'
'Sergei Kurbatov'
'Régis Goumont'
_publ_contact_author
;
Francois Terrier
;
_publ_contact_author_email       terrier@chimie.uvsq.fr
_publ_contact_author_fax         '00 33 1 39 25 44 52'
_publ_contact_author_phone       '00 33 1 39 25 44 50'
_publ_section_title
;
Carbon Nucleophilicities of Indoles in SNAr Substitutions of
Superelectrophilic 7-Chloro-4,6-dinitrobenzofuroxan and -benzofurazan
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3305
_journal_page_last               3315
_journal_paper_doi               10.1021/jo900076r
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C22 H15 N5 O6'
_chemical_formula_sum            'C22 H15 N5 O6'
_chemical_formula_weight         445.39
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.44(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.957(4)
_cell_length_b                   24.80(3)
_cell_length_c                   10.408(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19
_cell_measurement_theta_min      2
_cell_volume                     1970(4)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0778
_diffrn_reflns_av_sigmaI/netI    0.1022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10658
_diffrn_reflns_theta_full        24.92
_diffrn_reflns_theta_max         24.92
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1336
_refine_ls_R_factor_gt           0.0560
_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)+(0.0621P)²+0.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1432
_reflns_number_gt                1809
_reflns_number_total             3337
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo900076r_si_002.cif
_cod_data_source_block           sk10-3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024487
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2809(3) 0.40255(10) 0.7541(2) 0.0473(7) Uani 1 1 d . . .
N2 N 0.1143(3) 0.23885(11) 0.8391(3) 0.0548(7) Uani 1 1 d . . .
N3 N 0.0778(4) 0.14874(12) 0.7891(3) 0.0743(9) Uani 1 1 d . . .
N4 N 0.2756(5) 0.08913(11) 0.6267(3) 0.0665(8) Uani 1 1 d . . .
N5 N 0.5664(4) 0.25753(13) 0.6017(3) 0.0575(7) Uani 1 1 d . . .
O1 O 0.0236(3) 0.19107(11) 0.8549(3) 0.0769(7) Uani 1 1 d . . .
O2 O 0.0912(3) 0.27847(10) 0.8996(2) 0.0656(7) Uani 1 1 d . . .
O3 O 0.1556(4) 0.06548(10) 0.6531(3) 0.1033(11) Uani 1 1 d . . .
O4 O 0.3766(5) 0.06946(10) 0.5722(3) 0.0956(10) Uani 1 1 d . . .
O5 O 0.7123(3) 0.23858(11) 0.6277(3) 0.0868(8) Uani 1 1 d . . .
O6 O 0.5177(4) 0.29630(11) 0.5298(3) 0.0822(8) Uani 1 1 d . . .
C1 C 0.0264(4) 0.34393(13) 0.6489(3) 0.0568(9) Uani 1 1 d . . .
H1A H -0.0417 0.3515 0.7096 0.085 Uiso 1 1 calc R . .
H1B H 0.0082 0.3072 0.6195 0.085 Uiso 1 1 calc R . .
H1C H -0.0091 0.3675 0.5729 0.085 Uiso 1 1 calc R . .
C2 C 0.2152(4) 0.35262(12) 0.7183(3) 0.0433(8) Uani 1 1 d . . .
C3 C 0.3516(3) 0.31601(12) 0.7468(3) 0.0406(7) Uani 1 1 d . . .
C4 C 0.6870(4) 0.33158(12) 0.8611(3) 0.0461(8) Uani 1 1 d . . .
H4 H 0.7237 0.2960 0.8605 0.055 Uiso 1 1 calc R . .
C5 C 0.8037(4) 0.37150(13) 0.9170(3) 0.0545(9) Uani 1 1 d . . .
H5 H 0.9209 0.3627 0.9549 0.065 Uiso 1 1 calc R . .
C6 C 0.7514(4) 0.42431(13) 0.9183(3) 0.0586(9) Uani 1 1 d . . .
H6 H 0.8341 0.4505 0.9566 0.070 Uiso 1 1 calc R . .
C7 C 0.5799(4) 0.43923(12) 0.8642(3) 0.0540(9) Uani 1 1 d . . .
H7 H 0.5450 0.4750 0.8650 0.065 Uiso 1 1 calc R . .
C8 C 0.4615(4) 0.39929(12) 0.8088(3) 0.0421(7) Uani 1 1 d . . .
C9 C 0.5112(4) 0.34568(11) 0.8047(3) 0.0408(7) Uani 1 1 d . . .
C10 C 0.1822(4) 0.45280(12) 0.7414(3) 0.0585(9) Uani 1 1 d . . .
H10A H 0.2043 0.4693 0.8291 0.070 Uiso 1 1 calc R . .
H10B H 0.0580 0.4448 0.7094 0.070 Uiso 1 1 calc R . .
C11 C 0.2290(4) 0.49211(12) 0.6474(3) 0.0490(8) Uani 1 1 d . . .
C12 C 0.2583(4) 0.54514(14) 0.6838(4) 0.0681(10) Uani 1 1 d . . .
H12 H 0.2480 0.5567 0.7663 0.082 Uiso 1 1 calc R . .
C13 C 0.3035(5) 0.58184(15) 0.5974(5) 0.0764(11) Uani 1 1 d . . .
H13 H 0.3242 0.6178 0.6225 0.092 Uiso 1 1 calc R . .
C14 C 0.3172(5) 0.56510(18) 0.4773(5) 0.0750(11) Uani 1 1 d . . .
H14 H 0.3495 0.5893 0.4204 0.090 Uiso 1 1 calc R . .
C15 C 0.2839(5) 0.51294(17) 0.4398(4) 0.0758(11) Uani 1 1 d . . .
H15 H 0.2907 0.5017 0.3562 0.091 Uiso 1 1 calc R . .
C16 C 0.2402(4) 0.47672(14) 0.5242(4) 0.0648(10) Uani 1 1 d . . .
H16 H 0.2178 0.4411 0.4972 0.078 Uiso 1 1 calc R . .
C4' C 0.2977(4) 0.14540(12) 0.6632(3) 0.0524(8) Uani 1 1 d . . .
C5' C 0.4210(4) 0.17481(12) 0.6299(3) 0.0513(8) Uani 1 1 d . . .
H5' H 0.4964 0.1581 0.5884 0.062 Uiso 1 1 calc R . .
C6' C 0.4378(4) 0.23007(12) 0.6565(3) 0.0439(8) Uani 1 1 d . . .
C7' C 0.3359(3) 0.25941(11) 0.7186(3) 0.0415(7) Uani 1 1 d . . .
C8' C 0.2150(4) 0.22578(12) 0.7593(3) 0.0447(8) Uani 1 1 d . . .
C9' C 0.1919(4) 0.17043(12) 0.7340(3) 0.0502(8) 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
_geom_angle_publ_flag
C2 N1 C8 109.4(2) . . ?
C2 N1 C10 126.9(3) . . ?
C8 N1 C10 123.7(3) . . ?
O2 N2 C8' 136.2(3) . . ?
O2 N2 O1 117.4(3) . . ?
C8' N2 O1 106.3(3) . . ?
C9' N3 O1 104.8(3) . . ?
O4 N4 O3 125.4(3) . . ?
O4 N4 C4' 117.7(3) . . ?
O3 N4 C4' 116.9(4) . . ?
O5 N5 O6 124.4(3) . . ?
O5 N5 C6' 117.5(3) . . ?
O6 N5 C6' 118.1(3) . . ?
N3 O1 N2 109.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 108.9(3) . . ?
N1 C2 C1 121.6(3) . . ?
C3 C2 C1 129.3(3) . . ?
C2 C3 C7' 125.6(3) . . ?
C2 C3 C9 107.4(3) . . ?
C7' C3 C9 126.9(3) . . ?
C5 C4 C9 118.3(3) . . ?
C5 C4 H4 120.8 . . ?
C9 C4 H4 120.8 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 117.5(3) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C7 C8 N1 129.5(3) . . ?
C7 C8 C9 122.3(3) . . ?
N1 C8 C9 108.2(2) . . ?
C8 C9 C4 119.0(3) . . ?
C8 C9 C3 106.0(2) . . ?
C4 C9 C3 134.8(3) . . ?
N1 C10 C11 112.8(2) . . ?
N1 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N1 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C16 C11 C12 118.5(3) . . ?
C16 C11 C10 121.7(3) . . ?
C12 C11 C10 119.8(3) . . ?
C11 C12 C13 120.1(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.9(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 120.4(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 121.0(4) . . ?
C11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C5' C4' C9' 118.9(3) . . ?
C5' C4' N4 120.0(3) . . ?
C9' C4' N4 121.1(3) . . ?
C4' C5' C6' 121.1(3) . . ?
C4' C5' H5' 119.4 . . ?
C6' C5' H5' 119.4 . . ?
C7' C6' C5' 125.1(3) . . ?
C7' C6' N5 120.2(3) . . ?
C5' C6' N5 114.5(3) . . ?
C6' C7' C8' 111.5(3) . . ?
C6' C7' C3 125.7(3) . . ?
C8' C7' C3 122.7(3) . . ?
N2 C8' C9' 106.4(3) . . ?
N2 C8' C7' 127.7(3) . . ?
C9' C8' C7' 125.6(3) . . ?
N3 C9' C8' 112.8(3) . . ?
N3 C9' C4' 129.4(3) . . ?
C8' C9' C4' 117.7(3) . . ?
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
N1 C2 1.355(4) . ?
N1 C8 1.391(4) . ?
N1 C10 1.459(4) . ?
N2 O2 1.209(3) . ?
N2 C8' 1.347(4) . ?
N2 O1 1.421(3) . ?
N3 C9' 1.318(4) . ?
N3 O1 1.387(4) . ?
N4 O4 1.210(4) . ?
N4 O3 1.216(4) . ?
N4 C4' 1.444(4) . ?
N5 O5 1.211(3) . ?
N5 O6 1.212(3) . ?
N5 C6' 1.472(4) . ?
C1 C2 1.487(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.382(4) . ?
C3 C7' 1.432(4) . ?
C3 C9 1.444(4) . ?
C4 C5 1.369(4) . ?
C4 C9 1.399(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.391(4) . ?
C10 C11 1.501(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C16 1.364(5) . ?
C11 C12 1.370(4) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C4' C5' 1.344(4) . ?
C4' C9' 1.410(4) . ?
C5' C6' 1.397(4) . ?
C5' H5' 0.9300 . ?
C6' C7' 1.379(4) . ?
C7' C8' 1.425(4) . ?
C8' C9' 1.400(4) . ?
