#------------------------------------------------------------------------------
#$Date: 2018-06-07 07:44:05 +0300 (Thu, 07 Jun 2018) $
#$Revision: 208160 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/99/4029939.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_4029939
loop_
_publ_author_name
'Bergman, Jan'
'Arewång, Carl-Johan'
'Svensson, Per H.'
_publ_section_title
;
 Oxidative ring expansion of spirocyclic oxindole derivatives.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9065
_journal_page_last               9073
_journal_paper_doi               10.1021/jo501269f
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C15 H9 N3 O2'
_chemical_formula_sum            'C15 H9 N3 O2'
_chemical_formula_weight         263.25
_chemical_name_systematic
; 
 6H-quinazolino[4,3-b]quinazoline-6,8(5H)-dione
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        '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                97.816(3)
_cell_angle_beta                 93.664(2)
_cell_angle_gamma                113.447(3)
_cell_formula_units_Z            2
_cell_length_a                   7.0598(4)
_cell_length_b                   8.4940(5)
_cell_length_c                   10.5944(6)
_cell_measurement_reflns_used    3448
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      2.66
_cell_volume                     572.54(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      200(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16824
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0415
_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)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1014
_refine_ls_wR_factor_ref         0.1117
_reflns_number_gt                1454
_reflns_number_total             2120
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo501269f_si_002.cif
_cod_data_source_block           quinazolinoquinazolinedione
_cod_depositor_comments
;
 Updating space group information.

 Antanas Vaitkus,
 2018-06-07

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 4029939--4029940.cif.

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_sg_symbol_H-M      P-1
_cod_database_code               4029939
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -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
C7 C 0.2421(2) 0.5658(2) 0.56450(14) 0.0225(4) Uani 1 1 d .
C9 C 0.2739(2) 0.5147(2) 0.43324(14) 0.0237(4) Uani 1 1 d .
C1 C 0.2027(2) 0.6594(2) 0.81697(15) 0.0249(4) Uani 1 1 d .
N1 N 0.2758(2) 0.72540(17) 0.60440(12) 0.0264(4) Uani 1 1 d .
N2 N 0.1769(2) 0.43439(15) 0.64085(11) 0.0226(3) Uani 1 1 d .
N3 N 0.1594(2) 0.22129(17) 0.46839(12) 0.0285(4) Uani 1 1 d .
H16 H 0.1439 0.1164 0.4407 0.034 Uiso 1 1 calc R
C6 C 0.2491(2) 0.7746(2) 0.73078(14) 0.0245(4) Uani 1 1 d .
C10 C 0.2371(2) 0.3424(2) 0.38859(15) 0.0250(4) Uani 1 1 d .
C12 C 0.3418(2) 0.6360(2) 0.35088(15) 0.0284(4) Uani 1 1 d .
H12 H 0.3672 0.7519 0.3795 0.034 Uiso 1 1 calc R
O1 O 0.16220(18) 0.37831(14) 0.84878(10) 0.0364(4) Uani 1 1 d .
C15 C 0.2691(3) 0.2909(2) 0.26420(16) 0.0313(4) Uani 1 1 d .
H15 H 0.2467 0.1758 0.2352 0.038 Uiso 1 1 calc R
C14 C 0.3338(3) 0.4118(2) 0.18501(16) 0.0344(5) Uani 1 1 d .
H14 H 0.3528 0.3776 0.1013 0.041 Uiso 1 1 calc R
C5 C 0.2696(3) 0.9444(2) 0.77014(16) 0.0306(4) Uani 1 1 d .
H5 H 0.3028 1.0228 0.7132 0.037 Uiso 1 1 calc R
C4 C 0.2405(3) 0.9961(2) 0.89351(17) 0.0373(5) Uani 1 1 d .
H4 H 0.2513 1.1088 0.9191 0.045 Uiso 1 1 calc R
O2 O 0.00313(19) 0.13904(14) 0.64133(11) 0.0370(4) Uani 1 1 d .
C8 C 0.1780(2) 0.4802(2) 0.77707(15) 0.0256(4) Uani 1 1 d .
C2 C 0.1780(3) 0.7147(2) 0.94282(16) 0.0324(4) Uani 1 1 d .
H2 H 0.1500 0.6386 1.0013 0.039 Uiso 1 1 calc R
C13 C 0.3712(3) 0.5843(2) 0.22774(16) 0.0339(4) Uani 1 1 d .
H13 H 0.4163 0.6652 0.1731 0.041 Uiso 1 1 calc R
C11 C 0.1061(3) 0.2542(2) 0.58549(15) 0.0274(4) Uani 1 1 d .
C3 C 0.1952(3) 0.8814(2) 0.97997(17) 0.0376(5) Uani 1 1 d .
H3 H 0.1765 0.9176 1.0633 0.045 Uiso 1 1 calc R
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
N1 C7 N2 123.89(14)
N1 C7 C9 118.95(14)
N2 C7 C9 117.16(13)
C10 C9 C12 118.99(14)
C10 C9 C7 119.58(15)
C12 C9 C7 121.43(14)
C6 C1 C2 119.83(15)
C6 C1 C8 120.52(14)
C2 C1 C8 119.64(15)
C7 N1 C6 118.85(14)
C7 N2 C11 121.27(13)
C7 N2 C8 120.14(12)
C11 N2 C8 118.59(13)
C11 N3 C10 125.41(13)
C11 N3 H16 117.3
C10 N3 H16 117.3
C1 C6 C5 119.71(15)
C1 C6 N1 121.85(14)
C5 C6 N1 118.44(15)
N3 C10 C9 118.63(14)
N3 C10 C15 120.65(14)
C9 C10 C15 120.66(15)
C13 C12 C9 120.18(15)
C13 C12 H12 119.9
C9 C12 H12 119.9
C14 C15 C10 119.24(16)
C14 C15 H15 120.4
C10 C15 H15 120.4
C15 C14 C13 120.97(16)
C15 C14 H14 119.5
C13 C14 H14 119.5
C4 C5 C6 119.83(16)
C4 C5 H5 120.1
C6 C5 H5 120.1
C5 C4 C3 120.52(16)
C5 C4 H4 119.7
C3 C4 H4 119.7
O1 C8 N2 121.90(14)
O1 C8 C1 124.70(14)
N2 C8 C1 113.39(13)
C3 C2 C1 119.97(16)
C3 C2 H2 120.0
C1 C2 H2 120.0
C12 C13 C14 119.96(16)
C12 C13 H13 120.0
C14 C13 H13 120.0
O2 C11 N3 122.62(14)
O2 C11 N2 121.63(14)
N3 C11 N2 115.75(14)
C2 C3 C4 120.11(16)
C2 C3 H3 119.9
C4 C3 H3 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C7 N1 1.284(2)
C7 N2 1.4128(19)
C7 C9 1.458(2)
C9 C10 1.388(2)
C9 C12 1.399(2)
C1 C6 1.388(2)
C1 C2 1.398(2)
C1 C8 1.459(2)
N1 C6 1.3949(19)
N2 C11 1.430(2)
N2 C8 1.4414(19)
N3 C11 1.3445(19)
N3 C10 1.3860(19)
N3 H16 0.8600
C6 C5 1.392(2)
C10 C15 1.392(2)
C12 C13 1.374(2)
C12 H12 0.9300
O1 C8 1.2050(18)
C15 C14 1.370(2)
C15 H15 0.9300
C14 C13 1.385(2)
C14 H14 0.9300
C5 C4 1.376(2)
C5 H5 0.9300
C4 C3 1.387(2)
C4 H4 0.9300
O2 C11 1.2174(18)
C2 C3 1.370(2)
C2 H2 0.9300
C13 H13 0.9300
C3 H3 0.9300
