#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:39:52 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180310 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/24/7152484.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_7152484
loop_
_publ_author_name
'Cao, Liming'
'Maciejewski, John P.'
'Elzner, Stephan'
'Amantini, David'
'Wipf, Peter'
_publ_section_title
;
 Synthesis of 1,2,4-triazines and the triazinoisoquinolinedione DEF ring
 system of noelaquinone.
;
_journal_issue                   30
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5811
_journal_page_last               5814
_journal_paper_doi               10.1039/c2ob25353d
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C11 H9 N3 O2'
_chemical_formula_weight         215.21
_chemical_name_systematic
;
?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.9819(5)
_cell_length_b                   6.5576(6)
_cell_length_c                   28.039(3)
_cell_measurement_reflns_used    1331
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.106
_cell_measurement_theta_min      3.152
_cell_volume                     916.01(16)
_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      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            4855
_diffrn_reflns_theta_full        58.83
_diffrn_reflns_theta_max         58.83
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.927
_exptl_absorpt_correction_T_max  0.9926
_exptl_absorpt_correction_T_min  0.8890
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0040(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         823
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0366
_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          0.0897
_refine_ls_wR_factor_ref         0.0933
_reflns_number_gt                702
_reflns_number_total             823
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25353d.txt
_cod_data_source_block           liming4b_0m
_cod_original_cell_volume        916.01(15)
_cod_database_code               7152484
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O1 O 0.9803(5) 0.7587(3) 0.17288(8) 0.0302(7) Uani 1 1 d .
N1 N 1.4702(6) 0.7061(4) 0.08004(9) 0.0211(7) Uani 1 1 d .
C1 C 1.1671(7) 0.6900(5) 0.15019(12) 0.0218(8) Uani 1 1 d .
O2 O 1.8126(5) 0.4850(4) 0.07027(8) 0.0264(7) Uani 1 1 d .
C2 C 1.3120(7) 0.5024(5) 0.16471(11) 0.0209(8) Uani 1 1 d .
N2 N 1.5305(6) 0.7922(4) 0.03427(10) 0.0227(7) Uani 1 1 d .
H2N H 1.710(9) 0.744(6) 0.0257(13) 0.047(12) Uiso 1 1 d .
N3 N 1.1443(6) 0.9630(4) 0.09355(10) 0.0243(7) Uani 1 1 d .
C3 C 1.2307(7) 0.3954(5) 0.20508(12) 0.0232(9) Uani 1 1 d .
H3A H 1.0837 0.4432 0.2236 0.028 Uiso 1 1 calc R
C4 C 1.3644(7) 0.2194(5) 0.21825(12) 0.0266(9) Uani 1 1 d .
H4A H 1.3078 0.1451 0.2455 0.032 Uiso 1 1 calc R
C5 C 1.5808(7) 0.1514(5) 0.19159(12) 0.0253(9) Uani 1 1 d .
H5A H 1.6722 0.0305 0.2008 0.030 Uiso 1 1 calc R
C6 C 1.6651(7) 0.2579(5) 0.15168(11) 0.0228(9) Uani 1 1 d .
H6A H 1.8143 0.2108 0.1337 0.027 Uiso 1 1 calc R
C7 C 1.5302(7) 0.4343(5) 0.13807(11) 0.0196(8) Uani 1 1 d .
C8 C 1.6205(7) 0.5407(5) 0.09433(12) 0.0217(9) Uani 1 1 d .
C9 C 1.5262(7) 1.0149(5) 0.03805(12) 0.0237(8) Uani 1 1 d .
H9A H 1.5735 1.0776 0.0070 0.028 Uiso 1 1 calc R
H9B H 1.6572 1.0614 0.0623 0.028 Uiso 1 1 calc R
C10 C 1.2447(7) 1.0752(5) 0.05247(12) 0.0240(9) Uani 1 1 d .
H10A H 1.2422 1.2228 0.0599 0.029 Uiso 1 1 calc R
H10C H 1.1225 1.0522 0.0252 0.029 Uiso 1 1 calc R
C11 C 1.2596(7) 0.7973(5) 0.10543(11) 0.0202(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 0.0181 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
C8 N1 C11 126.5(3)
C8 N1 N2 117.2(3)
C11 N1 N2 116.3(3)
O1 C1 C2 122.5(3)
O1 C1 C11 119.8(3)
C2 C1 C11 117.8(3)
C7 C2 C3 120.1(3)
C7 C2 C1 119.9(3)
C3 C2 C1 120.0(3)
N1 N2 C9 109.0(3)
N1 N2 H2N 107(2)
C9 N2 H2N 111(2)
C11 N3 C10 118.9(3)
C4 C3 C2 119.8(3)
C4 C3 H3A 120.1
C2 C3 H3A 120.1
C3 C4 C5 120.0(3)
C3 C4 H4A 120.0
C5 C4 H4A 120.0
C6 C5 C4 120.7(3)
C6 C5 H5A 119.7
C4 C5 H5A 119.7
C5 C6 C7 119.6(3)
C5 C6 H6A 120.2
C7 C6 H6A 120.2
C6 C7 C2 119.8(3)
C6 C7 C8 118.2(3)
C2 C7 C8 122.0(3)
O2 C8 N1 119.9(3)
O2 C8 C7 123.5(3)
N1 C8 C7 116.5(3)
N2 C9 C10 107.1(3)
N2 C9 H9A 110.3
C10 C9 H9A 110.3
N2 C9 H9B 110.3
C10 C9 H9B 110.3
H9A C9 H9B 108.6
N3 C10 C9 113.5(3)
N3 C10 H10A 108.9
C9 C10 H10A 108.9
N3 C10 H10C 108.9
C9 C10 H10C 108.9
H10A C10 H10C 107.7
N3 C11 N1 124.6(3)
N3 C11 C1 118.5(3)
N1 C11 C1 116.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.214(4)
N1 C8 1.378(4)
N1 C11 1.402(4)
N1 N2 1.434(4)
C1 C2 1.483(5)
C1 C11 1.511(5)
O2 C8 1.227(4)
C2 C7 1.393(5)
C2 C3 1.392(5)
N2 C9 1.465(4)
N2 H2N 0.98(4)
N3 C11 1.273(4)
N3 C10 1.456(4)
C3 C4 1.383(5)
C3 H3A 0.9500
C4 C5 1.386(5)
C4 H4A 0.9500
C5 C6 1.384(5)
C5 H5A 0.9500
C6 C7 1.391(4)
C6 H6A 0.9500
C7 C8 1.481(5)
C9 C10 1.512(5)
C9 H9A 0.9900
C9 H9B 0.9900
C10 H10A 0.9900
C10 H10C 0.9900
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
N2 H2N N2 0.98(4) 2.33(4) 3.194(3) 147(3) 4_565
