#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/17/2221770.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2221770
loop_
_publ_author_name
'Qin, Jing'
_publ_section_title
;Diethyl
 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-tetraazabenzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate
;
_journal_coeditor_code           NC2142
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1100
_journal_paper_doi               10.1107/S1600536809014548
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C18 H20 N4 O6'
_chemical_formula_sum            'C18 H20 N4 O6'
_chemical_formula_weight         388.38
_chemical_name_systematic
;
Diethyl 1,4-dioxo-1,2,2a,3,4,10b-hexahydro-5H,10H-2,3,4a,10a-
tetraazabenzo[g]cyclopenta[cd]azulene-2a,10b-dicarboxylate
;
_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                93.1550(10)
_cell_angle_beta                 96.0560(10)
_cell_angle_gamma                112.3970(10)
_cell_formula_units_Z            2
_cell_length_a                   8.1394(5)
_cell_length_b                   9.4425(5)
_cell_length_c                   13.3576(8)
_cell_measurement_reflns_used    3262
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.35
_cell_volume                     938.80(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker SMART 4K CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7700
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.54
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_correction_T_min  0.9764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.198
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3624
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0741P)²+0.3055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1439
_reflns_number_gt                3028
_reflns_number_total             3624
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2142.cif
_cod_data_source_block           I
_cod_database_code               2221770
_cod_database_fobs_code          2221770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.7535(3) 0.3332(2) 0.06082(12) 0.0350(4) Uani d . 1 . .
C C2 0.6905(3) 0.1940(2) 0.00001(15) 0.0442(5) Uani d . 1 . .
H H2 0.5714 0.1512 -0.0298 0.053 Uiso calc R 1 . .
C C3 0.8025(3) 0.1180(2) -0.01692(16) 0.0516(5) Uani d . 1 . .
H H3 0.7589 0.0250 -0.0579 0.062 Uiso calc R 1 . .
C C4 0.9787(3) 0.1811(2) 0.02733(16) 0.0515(5) Uani d . 1 . .
H H4 1.0552 0.1318 0.0152 0.062 Uiso calc R 1 . .
C C5 1.0421(3) 0.3177(2) 0.08982(15) 0.0437(5) Uani d . 1 . .
H H5 1.1607 0.3581 0.1207 0.052 Uiso calc R 1 . .
C C6 0.9321(2) 0.3955(2) 0.10733(12) 0.0352(4) Uani d . 1 . .
C C7 0.6302(3) 0.4178(2) 0.07030(12) 0.0375(4) Uani d . 1 . .
H H7A 0.6781 0.5130 0.0391 0.045 Uiso calc R 1 . .
H H7B 0.5141 0.3556 0.0321 0.045 Uiso calc R 1 . .
C C8 1.0095(2) 0.5470(2) 0.17322(13) 0.0359(4) Uani d . 1 . .
H H8A 1.1323 0.5666 0.2006 0.043 Uiso calc R 1 . .
H H8B 1.0123 0.6287 0.1316 0.043 Uiso calc R 1 . .
C C9 0.4886(3) 0.3441(2) 0.22434(14) 0.0392(4) Uani d . 1 . .
C C10 0.9584(3) 0.5307(2) 0.35329(13) 0.0395(4) Uani d . 1 . .
C C11 0.7426(2) 0.5735(2) 0.24235(12) 0.0330(4) Uani d . 1 . .
C C12 0.7751(3) 0.7358(2) 0.20982(13) 0.0372(4) Uani d . 1 . .
C C13 0.9500(4) 1.0015(3) 0.2570(2) 0.0691(7) Uani d . 1 . .
H H13A 1.0481 1.0306 0.2168 0.083 Uiso calc R 1 . .
H H13B 0.8494 1.0152 0.2195 0.083 Uiso calc R 1 . .
C C14 1.0045(7) 1.0966(3) 0.3520(3) 0.1181(14) Uani d . 1 . .
H H14A 0.9041 1.0729 0.3891 0.177 Uiso calc R 1 . .
H H14B 1.0469 1.2031 0.3398 0.177 Uiso calc R 1 . .
H H14C 1.0988 1.0774 0.3906 0.177 Uiso calc R 1 . .
C C15 0.6771(3) 0.5423(2) 0.34897(13) 0.0379(4) Uani d . 1 . .
C C16 0.6154(3) 0.6578(2) 0.40178(14) 0.0412(4) Uani d . 1 . .
C C17 0.4679(4) 0.8288(3) 0.3831(2) 0.0741(8) Uani d . 1 . .
H H17A 0.5609 0.9012 0.4335 0.089 Uiso calc R 1 . .
H H17B 0.3639 0.7756 0.4160 0.089 Uiso calc R 1 . .
C C18 0.4201(6) 0.9114(4) 0.3022(3) 0.1120(13) Uani d . 1 . .
H H18A 0.5252 0.9687 0.2727 0.168 Uiso calc R 1 . .
H H18B 0.3718 0.9808 0.3300 0.168 Uiso calc R 1 . .
H H18C 0.3321 0.8386 0.2511 0.168 Uiso calc R 1 . .
N N1 0.6035(2) 0.45511(17) 0.17377(10) 0.0356(4) Uani d . 1 . .
N N2 0.9101(2) 0.55255(17) 0.25637(10) 0.0345(4) Uani d . 1 . .
N N3 0.5268(3) 0.3968(2) 0.32473(13) 0.0491(4) Uani d . 1 . .
H H3A 0.456(3) 0.355(3) 0.3683(19) 0.059 Uiso d . 1 . .
N N4 0.8307(3) 0.5358(2) 0.40898(13) 0.0532(5) Uani d . 1 . .
H H4A 0.835(3) 0.525(3) 0.472(2) 0.064 Uiso d . 1 . .
O O1 0.37312(19) 0.22369(16) 0.18597(12) 0.0528(4) Uani d . 1 . .
O O2 1.0959(2) 0.51339(19) 0.38374(10) 0.0531(4) Uani d . 1 . .
O O3 0.7018(2) 0.75960(17) 0.13482(10) 0.0552(4) Uani d . 1 . .
O O4 0.8984(2) 0.84003(15) 0.27670(11) 0.0526(4) Uani d . 1 . .
O O5 0.6376(3) 0.68292(19) 0.49151(11) 0.0644(5) Uani d . 1 . .
O O6 0.5323(2) 0.71765(18) 0.33836(11) 0.0556(4) Uani d . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.23(17) ?
C2 C1 C7 . . 119.00(17) ?
C6 C1 C7 . . 121.69(16) ?
C3 C2 C1 . . 121.0(2) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C4 C3 C2 . . 119.5(2) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C3 C4 C5 . . 120.1(2) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C4 C5 C6 . . 121.16(19) ?
C4 C5 H5 . . 119.4 ?
C6 C5 H5 . . 119.4 ?
C5 C6 C1 . . 118.94(18) ?
C5 C6 C8 . . 119.12(17) ?
C1 C6 C8 . . 121.91(16) ?
N1 C7 C1 . . 115.68(14) ?
N1 C7 H7A . . 108.4 ?
C1 C7 H7A . . 108.4 ?
N1 C7 H7B . . 108.4 ?
C1 C7 H7B . . 108.4 ?
H7A C7 H7B . . 107.4 ?
N2 C8 C6 . . 113.76(15) ?
N2 C8 H8A . . 108.8 ?
C6 C8 H8A . . 108.8 ?
N2 C8 H8B . . 108.8 ?
C6 C8 H8B . . 108.8 ?
H8A C8 H8B . . 107.7 ?
O1 C9 N3 . . 126.68(18) ?
O1 C9 N1 . . 125.85(18) ?
N3 C9 N1 . . 107.45(16) ?
O2 C10 N4 . . 126.78(16) ?
O2 C10 N2 . . 125.11(18) ?
N4 C10 N2 . . 108.09(16) ?
N1 C11 N2 . . 113.91(14) ?
N1 C11 C12 . . 111.49(13) ?
N2 C11 C12 . . 109.92(14) ?
N1 C11 C15 . . 103.63(14) ?
N2 C11 C15 . . 101.80(13) ?
C12 C11 C15 . . 115.76(14) ?
O3 C12 O4 . . 126.43(17) ?
O3 C12 C11 . . 124.36(17) ?
O4 C12 C11 . . 109.19(14) ?
C14 C13 O4 . . 108.9(2) ?
C14 C13 H13A . . 109.9 ?
O4 C13 H13A . . 109.9 ?
C14 C13 H13B . . 109.9 ?
O4 C13 H13B . . 109.9 ?
H13A C13 H13B . . 108.3 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
N4 C15 N3 . . 114.94(17) ?
N4 C15 C16 . . 110.13(16) ?
N3 C15 C16 . . 109.09(16) ?
N4 C15 C11 . . 102.62(15) ?
N3 C15 C11 . . 101.34(14) ?
C16 C15 C11 . . 118.67(15) ?
O5 C16 O6 . . 125.5(2) ?
O5 C16 C15 . . 121.54(18) ?
O6 C16 C15 . . 112.92(15) ?
O6 C17 C18 . . 108.6(3) ?
O6 C17 H17A . . 110.0 ?
C18 C17 H17A . . 110.0 ?
O6 C17 H17B . . 110.0 ?
C18 C17 H17B . . 110.0 ?
H17A C17 H17B . . 108.3 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C9 N1 C11 . . 111.93(14) ?
C9 N1 C7 . . 120.52(15) ?
C11 N1 C7 . . 121.64(15) ?
C10 N2 C11 . . 113.25(15) ?
C10 N2 C8 . . 124.21(15) ?
C11 N2 C8 . . 122.46(13) ?
C9 N3 C15 . . 114.32(16) ?
C9 N3 H3A . . 122.6(16) ?
C15 N3 H3A . . 122.3(16) ?
C10 N4 C15 . . 113.12(15) ?
C10 N4 H4A . . 123.5(17) ?
C15 N4 H4A . . 123.0(17) ?
C12 O4 C13 . . 116.92(16) ?
C16 O6 C17 . . 116.28(18) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.390(3) ?
C1 C6 . 1.401(3) ?
C1 C7 . 1.513(2) ?
C2 C3 . 1.386(3) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.375(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.382(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.387(3) ?
C5 H5 . 0.9300 ?
C6 C8 . 1.508(3) ?
C7 N1 . 1.466(2) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 N2 . 1.451(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 O1 . 1.208(2) ?
C9 N3 . 1.365(3) ?
C9 N1 . 1.376(2) ?
C10 O2 . 1.223(2) ?
C10 N4 . 1.354(3) ?
C10 N2 . 1.363(2) ?
C11 N1 . 1.440(2) ?
C11 N2 . 1.445(2) ?
C11 C12 . 1.548(2) ?
C11 C15 . 1.577(2) ?
C12 O3 . 1.188(2) ?
C12 O4 . 1.317(2) ?
C13 C14 . 1.437(4) ?
C13 O4 . 1.466(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 N4 . 1.437(2) ?
C15 N3 . 1.441(3) ?
C15 C16 . 1.531(3) ?
C16 O5 . 1.190(2) ?
C16 O6 . 1.311(2) ?
C17 O6 . 1.466(3) ?
C17 C18 . 1.471(4) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
N3 H3A . 0.87(3) ?
N4 H4A . 0.85(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C7 H7A O3 . 0.97 2.52 3.107(2) 118.6
C17 H17B O2 1_455 0.97 2.58 3.343(3) 135.9
C7 H7B O3 2_665 0.97 2.59 3.478(2) 152.8
N4 H4A O2 2_766 0.85(3) 2.05(3) 2.871(2) 165(2)
N3 H3A O5 2_666 0.87(3) 2.09(3) 2.917(2) 159(2)
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.4(3) ?
C7 C1 C2 C3 . . . . 175.22(17) ?
C1 C2 C3 C4 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . 1.3(3) ?
C3 C4 C5 C6 . . . . -1.5(3) ?
C4 C5 C6 C1 . . . . 0.3(3) ?
C4 C5 C6 C8 . . . . -177.86(17) ?
C2 C1 C6 C5 . . . . 1.2(2) ?
C7 C1 C6 C5 . . . . -175.36(16) ?
C2 C1 C6 C8 . . . . 179.26(16) ?
C7 C1 C6 C8 . . . . 2.7(2) ?
C2 C1 C7 N1 . . . . 124.69(18) ?
C6 C1 C7 N1 . . . . -58.8(2) ?
C5 C6 C8 N2 . . . . -126.25(17) ?
C1 C6 C8 N2 . . . . 55.7(2) ?
N1 C11 C12 O3 . . . . -3.8(3) ?
N2 C11 C12 O3 . . . . 123.5(2) ?
C15 C11 C12 O3 . . . . -121.9(2) ?
N1 C11 C12 O4 . . . . 177.71(15) ?
N2 C11 C12 O4 . . . . -55.00(19) ?
C15 C11 C12 O4 . . . . 59.6(2) ?
N1 C11 C15 N4 . . . . 127.94(15) ?
N2 C11 C15 N4 . . . . 9.48(18) ?
C12 C11 C15 N4 . . . . -109.69(17) ?
N1 C11 C15 N3 . . . . 8.88(17) ?
N2 C11 C15 N3 . . . . -109.58(15) ?
C12 C11 C15 N3 . . . . 131.26(16) ?
N1 C11 C15 C16 . . . . -110.44(17) ?
N2 C11 C15 C16 . . . . 131.09(17) ?
C12 C11 C15 C16 . . . . 11.9(2) ?
N4 C15 C16 O5 . . . . -29.5(3) ?
N3 C15 C16 O5 . . . . 97.5(2) ?
C11 C15 C16 O5 . . . . -147.25(19) ?
N4 C15 C16 O6 . . . . 153.07(17) ?
N3 C15 C16 O6 . . . . -79.91(19) ?
C11 C15 C16 O6 . . . . 35.3(2) ?
O1 C9 N1 C11 . . . . -171.16(18) ?
N3 C9 N1 C11 . . . . 10.2(2) ?
O1 C9 N1 C7 . . . . -17.8(3) ?
N3 C9 N1 C7 . . . . 163.56(16) ?
N2 C11 N1 C9 . . . . 97.72(17) ?
C12 C11 N1 C9 . . . . -137.17(15) ?
C15 C11 N1 C9 . . . . -12.01(18) ?
N2 C11 N1 C7 . . . . -55.3(2) ?
C12 C11 N1 C7 . . . . 69.8(2) ?
C15 C11 N1 C7 . . . . -165.00(14) ?
C1 C7 N1 C9 . . . . -78.3(2) ?
C1 C7 N1 C11 . . . . 72.4(2) ?
O2 C10 N2 C11 . . . . -178.59(18) ?
N4 C10 N2 C11 . . . . -0.2(2) ?
O2 C10 N2 C8 . . . . 4.8(3) ?
N4 C10 N2 C8 . . . . -176.82(17) ?
N1 C11 N2 C10 . . . . -116.92(17) ?
C12 C11 N2 C10 . . . . 117.15(16) ?
C15 C11 N2 C10 . . . . -6.07(19) ?
N1 C11 N2 C8 . . . . 59.8(2) ?
C12 C11 N2 C8 . . . . -66.1(2) ?
C15 C11 N2 C8 . . . . 170.64(15) ?
C6 C8 N2 C10 . . . . 99.2(2) ?
C6 C8 N2 C11 . . . . -77.2(2) ?
O1 C9 N3 C15 . . . . 177.73(18) ?
N1 C9 N3 C15 . . . . -3.7(2) ?
N4 C15 N3 C9 . . . . -113.33(19) ?
C16 C15 N3 C9 . . . . 122.44(18) ?
C11 C15 N3 C9 . . . . -3.5(2) ?
O2 C10 N4 C15 . . . . -174.2(2) ?
N2 C10 N4 C15 . . . . 7.4(2) ?
N3 C15 N4 C10 . . . . 98.4(2) ?
C16 C15 N4 C10 . . . . -137.96(18) ?
C11 C15 N4 C10 . . . . -10.7(2) ?
O3 C12 O4 C13 . . . . 0.2(3) ?
C11 C12 O4 C13 . . . . 178.62(19) ?
C14 C13 O4 C12 . . . . 150.2(3) ?
O5 C16 O6 C17 . . . . 2.3(3) ?
C15 C16 O6 C17 . . . . 179.63(19) ?
C18 C17 O6 C16 . . . . 166.1(2) ?
