#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/78/2007838.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_2007838
loop_
_publ_author_name
'Główka, Marek L.'
'Książek, Waldemar'
_publ_section_title
;
2-(1,2-Dihydro-1-oxophthalazin-2-yl)-4,5-dihydroimidazolium Iodide and
2-(1,2-Dihydro-1-oxophthalazin-2-yl)-4,5,6,7-tetrahydro-1,3-diazepinium
Iodide
;
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1691
_journal_page_last               1693
_journal_paper_doi               10.1107/S010827019800701X
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C13 H15 N4 O1 1+ , I 1-'
_chemical_formula_sum            'C13 H15 I N4 O'
_chemical_formula_weight         370.19
_chemical_name_systematic
;
 2-(4,5,6,7-Tetrahydrodiazepin2-yl)phthalazinone-1 Hydroiodides
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.43(3)
_cell_angle_beta                 73.15(3)
_cell_angle_gamma                83.58(3)
_cell_formula_units_Z            2
_cell_length_a                   8.196(2)
_cell_length_b                   8.550(2)
_cell_length_c                   10.787(2)
_cell_measurement_reflns_used    50
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      23
_cell_volume                     705.2(3)
_computing_cell_refinement       'KM-4 software'
_computing_data_collection       'KM-4 software'
_computing_data_reduction        'XDISK in SHELXTL/PC (Sheldrick, 1990a)'
_computing_molecular_graphics    'XP in SHELXTL/PC'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990b)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Kuma KM-4'
_diffrn_measurement_method       ω-2θ
_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  0.024
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3183
_diffrn_reflns_theta_full        80.99
_diffrn_reflns_theta_max         80.99
_diffrn_reflns_theta_min         4.37
_diffrn_standards_decay_%        5.15
_diffrn_standards_interval_count 100
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    17.83
_exptl_absorpt_correction_T_max  0.368
_exptl_absorpt_correction_T_min  0.125
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details   ' KM-4 software'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.743
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_refine_diff_density_max         1.125
_refine_diff_density_min         -1.405
_refine_ls_extinction_coef       0.0035(6)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2968
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.050
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0939P)²+0.0714P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.111
_refine_ls_wR_factor_ref         0.119
_reflns_number_gt                2650
_reflns_number_total             2968
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ka1276.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.0714P] where P = (Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0939P)^2^+0.0714P] where P = (Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_database_code               2007838
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
I -0.27841(3) -0.23799(3) 1.14983(2) 0.06100(15) Uani d . 1 . . I
O1 0.2865(4) 0.0755(4) 0.5127(3) 0.0650(8) Uani d . 1 . . O
C1 0.1386(5) 0.0857(5) 0.5789(4) 0.0545(8) Uani d . 1 . . C
N2 0.0782(4) -0.0168(5) 0.7012(3) 0.0527(7) Uani d . 1 . . N
N3 -0.0885(5) -0.0105(5) 0.7812(3) 0.0604(8) Uani d . 1 . . N
C4 -0.1956(5) 0.0963(6) 0.7404(4) 0.0599(9) Uani d . 1 . . C
H4 -0.3070 0.0998 0.7941 0.073(17) Uiso calc R 1 . . H
C5 -0.2753(6) 0.3264(7) 0.5807(5) 0.0645(10) Uani d . 1 . . C
H5 -0.3857 0.3328 0.6356 0.09(2) Uiso calc R 1 . . H
C6 -0.2281(6) 0.4314(7) 0.4614(5) 0.0663(11) Uani d . 1 . . C
H6 -0.3064 0.5104 0.4364 0.059(13) Uiso calc R 1 . . H
C7 -0.0633(6) 0.4199(6) 0.3778(4) 0.0635(10) Uani d . 1 . . C
H7 -0.0340 0.4893 0.2963 0.071(16) Uiso calc R 1 . . H
C8 0.0562(6) 0.3072(6) 0.4144(4) 0.0584(9) Uani d . 1 . . C
H8 0.1658 0.3007 0.3583 0.11(3) Uiso calc R 1 . . H
C9 0.0115(5) 0.2022(5) 0.5368(4) 0.0532(8) Uani d . 1 . . C
C10 -0.1547(5) 0.2093(6) 0.6189(4) 0.0555(8) Uani d . 1 . . C
N21 0.1075(5) -0.2161(5) 0.8788(4) 0.0589(8) Uani d . 1 . . N
H21 0.000(8) -0.201(7) 0.905(6) 0.061(14) Uiso d . 1 . . H
C22 0.1816(5) -0.1366(5) 0.7611(4) 0.0531(8) Uani d . 1 . . C
N23 0.3402(5) -0.1611(5) 0.6944(4) 0.0584(8) Uani d . 1 . . N
H23 0.376(6) -0.108(7) 0.623(5) 0.050(12) Uiso d . 1 . . H
C24 0.4459(6) -0.3050(6) 0.7309(4) 0.0621(10) Uani d . 1 . . C
H14 0.5425 -0.3168 0.6557 0.079(18) Uiso calc R 1 . . H
H24 0.3791 -0.3989 0.7527 0.057(13) Uiso calc R 1 . . H
C25 0.5108(7) -0.2972(7) 0.8472(5) 0.0686(11) Uani d . 1 . . C
H15 0.5962 -0.2175 0.8200 0.10(2) Uiso calc R 1 . . H
H25 0.5647 -0.4003 0.8758 0.10(2) Uiso calc R 1 . . H
C26 0.3664(7) -0.2541(7) 0.9623(5) 0.0667(11) Uani d . 1 . . C
H16 0.3539 -0.1382 0.9524 0.050(12) Uiso calc R 1 . . H
H26 0.3973 -0.2969 1.0439 0.078(17) Uiso calc R 1 . . H
C27 0.1947(7) -0.3177(7) 0.9729(5) 0.0678(11) Uani d . 1 . . C
H17 0.2130 -0.4260 0.9558 0.09(2) Uiso calc R 1 . . H
H27 0.1218 -0.3222 1.0622 0.069(16) Uiso calc R 1 . . H
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'
I I -0.3257 6.8362 '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_publ_flag
O1 C1 N2 121.8(4) ?
O1 C1 C9 123.0(4) ?
N2 C1 C9 115.1(3) ?
N3 N2 C1 124.5(4) y
N3 N2 C22 111.4(3) y
C1 N2 C22 124.1(3) y
C4 N3 N2 118.0(4) y
N3 C4 C10 124.5(4) ?
N3 C4 H4 117.7 ?
C10 C4 H4 117.7 ?
C6 C5 C10 119.4(4) ?
C6 C5 H5 120.3 ?
C10 C5 H5 120.3 ?
C5 C6 C7 120.4(4) ?
C5 C6 H6 119.8 ?
C7 C6 H6 119.8 ?
C8 C7 C6 120.8(4) ?
C8 C7 H7 119.6 ?
C6 C7 H7 119.6 ?
C7 C8 C9 119.5(4) ?
C7 C8 H8 120.3 ?
C9 C8 H8 120.3 ?
C10 C9 C8 120.0(4) ?
C10 C9 C1 120.0(4) ?
C8 C9 C1 120.1(4) ?
C9 C10 C5 119.9(4) ?
C9 C10 C4 117.9(4) ?
C5 C10 C4 122.2(4) ?
C22 N21 C27 126.2(4) ?
C22 N21 H21 116(4) ?
C27 N21 H21 117(4) ?
N21 C22 N23 125.4(4) ?
N21 C22 N2 116.3(4) y
N23 C22 N2 118.2(4) y
C22 N23 C24 122.8(4) ?
C22 N23 H23 120(4) ?
C24 N23 H23 116(4) ?
N23 C24 C25 112.5(4) ?
N23 C24 H14 109.1 ?
C25 C24 H14 109.1 ?
N23 C24 H24 109.1 ?
C25 C24 H24 109.1 ?
H14 C24 H24 107.8 ?
C24 C25 C26 111.5(4) ?
C24 C25 H15 109.3 ?
C26 C25 H15 109.3 ?
C24 C25 H25 109.3 ?
C26 C25 H25 109.3 ?
H15 C25 H25 108.0 ?
C25 C26 C27 113.7(4) ?
C25 C26 H16 108.8 ?
C27 C26 H16 108.8 ?
C25 C26 H26 108.8 ?
C27 C26 H26 108.8 ?
H16 C26 H26 107.7 ?
N21 C27 C26 112.2(4) ?
N21 C27 H17 109.2 ?
C26 C27 H17 109.2 ?
N21 C27 H27 109.2 ?
C26 C27 H27 109.2 ?
H17 C27 H27 107.9 ?
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
O1 C1 . 1.220(5) y
C1 N2 . 1.403(5) y
C1 C9 . 1.459(6) ?
N2 N3 . 1.391(5) y
N2 C22 . 1.422(5) y
N3 C4 . 1.292(6) y
C4 C10 . 1.425(6) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.378(7) ?
C5 C10 . 1.408(6) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.396(7) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.375(6) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.401(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.396(6) ?
N21 C22 . 1.308(5) y
N21 C27 . 1.481(6) ?
N21 H21 . 0.85(6) ?
C22 N23 . 1.308(6) y
N23 C24 . 1.473(6) ?
N23 H23 . 0.79(6) ?
C24 C25 . 1.514(7) ?
C24 H14 . 0.9700 ?
C24 H24 . 0.9700 ?
C25 C26 . 1.526(7) ?
C25 H15 . 0.9700 ?
C25 H25 . 0.9700 ?
C26 C27 . 1.530(8) ?
C26 H16 . 0.9700 ?
C26 H26 . 0.9700 ?
C27 H17 . 0.9700 ?
C27 H27 . 0.9700 ?
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
N23 H23 O1 . 0.79(6) 1.96(5) 2.589(5) 135(5)
N21 H21 I . 0.85(6) 2.93(6) 3.622(4) 140(5)
N23 H23 O1 2_656 0.79(6) 2.74(5) 3.274(5) 126(4)
C4 H4 I 2_457 0.93 3.40 4.237(4) 151.7
C5 H5 I 2_457 0.93 3.10 3.987(5) 161.2
C6 H6 I 1_564 0.93 3.32 3.983(5) 129.8
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_publ_flag
O1 C1 N2 N3 179.7(4) ?
C9 C1 N2 N3 -1.2(6) y
O1 C1 N2 C22 2.0(7) y
C9 C1 N2 C22 -178.8(4) ?
C1 N2 N3 C4 0.2(6) y
C22 N2 N3 C4 178.2(4) ?
N2 N3 C4 C10 -0.3(7) ?
C10 C5 C6 C7 1.3(8) ?
C5 C6 C7 C8 -2.0(8) ?
C6 C7 C8 C9 0.4(7) ?
C7 C8 C9 C10 1.9(7) ?
C7 C8 C9 C1 -177.9(4) ?
O1 C1 C9 C10 -178.7(4) ?
N2 C1 C9 C10 2.2(6) ?
O1 C1 C9 C8 1.1(7) ?
N2 C1 C9 C8 -178.0(4) ?
C8 C9 C10 C5 -2.6(7) ?
C1 C9 C10 C5 177.2(4) ?
C8 C9 C10 C4 177.9(4) ?
C1 C9 C10 C4 -2.3(6) ?
C6 C5 C10 C9 1.0(7) ?
C6 C5 C10 C4 -179.5(5) ?
N3 C4 C10 C9 1.3(7) ?
N3 C4 C10 C5 -178.2(5) ?
C27 N21 C22 N23 16.6(8) ?
C27 N21 C22 N2 -164.9(5) ?
N3 N2 C22 N21 -1.6(5) y
C1 N2 C22 N21 176.4(4) ?
N3 N2 C22 N23 177.0(4) ?
C1 N2 C22 N23 -5.0(6) y
N21 C22 N23 C24 13.8(7) ?
N2 C22 N23 C24 -164.7(4) ?
C22 N23 C24 C25 -77.1(6) ?
N23 C24 C25 C26 50.5(6) ?
C24 C25 C26 C27 32.4(6) ?
C22 N21 C27 C26 33.0(7) ?
C25 C26 C27 N21 -79.9(6) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136783
