#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/95/2009551.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_2009551
loop_
_publ_author_name
'Golič, L.'
'Sinur, A.'
'Stanovnik, B.'
'Žličar, M.'
_publ_section_title
;
 Two substituted
 pyrazolo[1',2':1,2]pyrazolo[4,3-d]tetrazolo[1,5-b]pyridazines
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              466
_journal_page_last               469
_journal_paper_doi               10.1107/S0108270193007838
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C23 H21 Cl N8 O6'
_chemical_formula_weight         540.5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source
'Cromer & Mann (1968) and Cromer & Liberman (1970)'
_cell_angle_alpha                90
_cell_angle_beta                 109.406(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.4371(8)
_cell_length_b                   17.8790(10)
_cell_length_c                   12.7762(9)
_cell_measurement_reflns_used    100
_cell_measurement_temperature    293.0(10)
_cell_measurement_theta_max      16
_cell_measurement_theta_min      9
_cell_volume                     2464.1(3)
_computing_cell_refinement       'XRAY76 (Stewart et al., 1976)'
_computing_data_collection       'XRAY76 (Stewart et al., 1976)'
_computing_molecular_graphics    'ORTEP (Johnson, 1965)'
_computing_structure_solution    'XRAY76 (Stewart et al., 1976)'
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.02
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12330
_diffrn_reflns_theta_max         27.9
_diffrn_standards_decay_%        -5.04
_diffrn_standards_interval_time  333
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.2067
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      1.44(2)
_exptl_crystal_density_method    'flotation in chlorobenzene/CCl~4~'
_exptl_crystal_description       Irregular
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.72
_exptl_crystal_size_min          0.56
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.20
_refine_ls_extinction_coef       'g = 1.508E-3'
_refine_ls_extinction_method     'Larson (1967)'
_refine_ls_goodness_of_fit_obs   0.998
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     426
_refine_ls_number_reflns         4492
_refine_ls_R_factor_obs          0.038
_refine_ls_shift/esd_max         0.088
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=empirical
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.050
_reflns_number_observed          3723
_reflns_number_total             5908
_reflns_observed_criterion       I>2.5\s
_cod_data_source_file            mu1060.cif
_cod_data_source_block           mu1060_structure_2_of_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=empirical' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w=empirical'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2464.1(6)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C23 H21 Cl1 N8 O6'
_cod_database_code               2009551
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
Cl .39110(10) .60021(3) .21316(5) .0678(3)
O(1) .41290(10) .40310(10) .09440(10) .0680(10)
O(2) .28130(10) .45810(10) -.05590(10) .0590(10)
O(3) .09650(10) .32260(10) -.08890(10) .0550(10)
O(4) -.00550(10) .43130(10) -.11320(10) .0460(10)
O(5) -.16570(10) .31850(10) -.01540(10) .0700(10)
O(6) .1353(2) .14160(10) .11260(10) .0650(10)
N(1) .6318(2) .36350(10) .50660(10) .0680(10)
N(2) .7371(2) .4057(2) .5467(2) .0820(10)
N(3) .7279(2) .4714(2) .5030(2) .0780(10)
N(4) .61160(10) .47390(10) .42820(10) .0600(10)
N(5) .5682(2) .53420(10) .3647(2) .0610(10)
N(6) .26370(10) .44690(10) .22250(10) .0370(10)
N(7) .22870(10) .37210(10) .25350(10) .0380(10)
N(8) -.00410(10) .23940(10) .07340(10) .0480(10)
C(1) .4551(2) .52580(10) .29740(10) .0500(10)
C(2) .38440(10) .45890(10) .28950(10) .0400(10)
C(3) .22040(10) .45510(10) .10160(10) .0370(10)
C(4) .11070(10) .39980(10) .06940(10) .0360(10)
C(5) .16030(10) .33420(10) .14910(10) .0360(10)
C(6) .3436(2) .33510(10) .33390(10) .0450(10)
C(7) .43160(10) .40010(10) .35770(10) .0440(10)
C(8) .5539(2) .40740(10) .43160(10) .0520(10)
C(9) .31800(10) .43490(10) .04870(10) .0420(10)
C(10) .3591(2) .4372(2) -.1206(2) .0760(10)
C(11) .06810(10) .37890(10) -.05230(10) .0380(10)
C(12) -.0556(2) .41570(10) -.23110(10) .0610(10)
C(13) .3973(2) .26990(10) .2864(2) .0660(10)
C(14) .3132(2) .31250(10) .4377(2) .0670(10)
C(15) .0594(2) .28550(10) .16930(10) .0470(10)
C(16) -.1102(2) .26080(10) -.0126(2) .0530(10)
C(17) -.1334(2) .19960(10) -.0963(2) .0560(10)
C(18) -.2269(2) .1921(2) -.1979(2) .0710(10)
C(19) -.2223(3) .1281(2) -.2594(2) .087(2)
C(20) -.1308(3) .0761(2) -.2221(2) .085(2)
C(21) -.0369(3) .08340(10) -.1200(2) .0730(10)
C(22) -.0417(2) .14690(10) -.0595(2) .0540(10)
C(23) .0439(2) .17140(10) .05140(10) .0510(10)
H(3) .193(2) .5040(10) .080(2) ?
H(4) .042(2) .4220(10) .085(2) ?
H(5) .212(2) .3050(10) .122(2) ?
H(18) -.282(3) .229(2) -.223(2) ?
H(19) -.280(4) .127(2) -.325(3) ?
H(20) -.134(3) .032(2) -.268(3) ?
H(21) .032(3) .043(2) -.092(3) ?
H(101) .416(4) .475(3) -.113(4) ?
H(102) .313(4) .437(2) -.197(3) ?
H(103) .407(4) .394(3) -.095(4) ?
H(121) .009(2) .4080(10) -.257(2) ?
H(122) -.107(3) .458(2) -.265(3) ?
H(123) -.107(3) .371(2) -.243(3) ?
H(131) .339(3) .231(2) .268(3) ?
H(132) .469(3) .251(2) .346(3) ?
H(133) .414(3) .284(2) .218(2) ?
H(141) .259(3) .273(2) .420(3) ?
H(142) .276(3) .356(2) .464(3) ?
H(143) .388(3) .294(2) .495(3) ?
H(151) .000(2) .3150(10) .186(2) ?
H(152) .094(2) .2520(10) .230(2) ?
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
N(5) C(1) Cl 116.6(2) yes
C(2) C(1) Cl 119.50(10) yes
O(2) C(9) O(1) 125.0(2) yes
C(3) C(9) O(1) 125.10(10) yes
C(10) O(2) C(9) 116.5(2) yes
C(3) C(9) O(2) 109.80(10) yes
O(4) C(11) O(3) 124.60(10) yes
C(4) C(11) O(3) 124.80(10) yes
C(12) O(4) C(11) 115.30(10) yes
C(4) C(11) O(4) 110.60(10) yes
C(14) C(6) N(7) 107.7(2) yes
C(16) N(8) C(15) 124.6(2) yes
C(23) N(8) C(15) 122.8(2) yes
C(5) C(15) N(8) 111.80(10) yes
C(23) N(8) C(16) 112.20(10) yes
C(17) C(16) N(8) 105.4(2) yes
C(22) C(23) N(8) 105.5(2) yes
C(7) C(2) C(1) 120.5(2) yes
C(6) C(7) C(2) 111.90(10) yes
C(8) C(7) C(2) 116.9(2) yes
N(8) C(16) O(5) 124.8(2) yes
C(17) C(16) O(5) 129.8(2) yes
N(8) C(23) O(6) 124.6(2) yes
C(22) C(23) O(6) 129.9(2) yes
C(8) N(1) N(2) 103.9(2) yes
N(3) N(2) N(1) 114.0(2) yes
N(4) C(8) N(1) 108.8(2) yes
C(7) C(8) N(1) 135.0(2) yes
N(4) N(3) N(2) 104.7(2) yes
N(5) N(4) N(3) 122.1(2) yes
C(8) N(4) N(3) 108.7(2) yes
C(8) N(4) N(5) 129.2(2) yes
C(1) N(5) N(4) 113.1(2) yes
C(7) C(8) N(4) 116.2(2) yes
C(2) C(1) N(5) 123.9(2) yes
C(2) N(6) N(7) 106.00(10) yes
C(3) N(6) N(7) 110.20(10) yes
C(5) N(7) N(6) 106.40(10) yes
C(6) N(7) N(6) 108.80(10) yes
C(3) N(6) C(2) 124.00(10) yes
C(1) C(2) N(6) 126.90(10) yes
C(7) C(2) N(6) 112.40(10) yes
C(4) C(3) N(6) 100.20(10) yes
C(9) C(3) N(6) 113.70(10) yes
C(9) C(3) C(4) 112.30(10) yes
C(5) C(4) C(3) 103.00(10) yes
C(11) C(4) C(3) 112.80(10) yes
C(11) C(4) C(5) 114.50(10) yes
C(15) C(5) C(4) 114.40(10) yes
C(13) C(6) C(7) 109.8(2) yes
C(14) C(6) C(7) 111.00(10) yes
C(8) C(7) C(6) 131.0(2) yes
C(14) C(6) C(13) 112.3(2) yes
C(18) C(17) C(16) 129.9(2) yes
C(22) C(17) C(16) 108.9(2) yes
C(22) C(17) C(18) 121.2(2) yes
C(19) C(18) C(17) 116.4(3) yes
C(21) C(22) C(17) 122.7(2) yes
C(23) C(22) C(17) 108.0(2) yes
C(20) C(19) C(18) 122.0(3) yes
C(21) C(20) C(19) 121.8(3) yes
C(22) C(21) C(20) 116.0(2) yes
C(23) C(22) C(21) 129.3(2) yes
C(6) N(7) C(5) 119.40(10) yes
C(4) C(5) N(7) 102.60(10) yes
C(15) C(5) N(7) 108.20(10) yes
C(7) C(6) N(7) 99.80(10) yes
C(13) C(6) N(7) 115.60(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C(1) 1.715(2) yes
O(1) C(9) 1.192(2) yes
O(2) C(9) 1.326(2) yes
O(2) C(10) 1.450(3) yes
O(3) C(11) 1.199(2) yes
O(4) C(11) 1.326(2) yes
C(16) C(17) 1.491(3) yes
C(17) C(18) 1.387(3) yes
C(17) C(22) 1.371(3) yes
C(18) C(19) 1.399(5) yes
C(19) C(20) 1.362(5) yes
C(20) C(21) 1.394(3) yes
O(4) C(12) 1.450(2) yes
O(5) C(16) 1.206(3) yes
O(6) C(23) 1.201(2) yes
N(1) N(2) 1.368(3) yes
N(1) C(8) 1.327(3) yes
N(2) N(3) 1.289(4) yes
N(3) N(4) 1.356(2) yes
N(4) N(5) 1.341(3) yes
N(4) C(8) 1.368(3) yes
N(5) C(1) 1.303(2) yes
N(6) N(7) 1.487(2) yes
N(6) C(2) 1.378(2) yes
N(6) C(3) 1.464(2) yes
N(7) C(5) 1.470(2) yes
N(7) C(6) 1.525(2) yes
N(8) C(15) 1.456(2) yes
C(21) C(22) 1.385(3) yes
C(22) C(23) 1.495(2) yes
N(8) C(23) 1.401(2) yes
C(1) C(2) 1.429(2) yes
C(2) C(7) 1.358(2) yes
C(3) C(4) 1.542(2) yes
C(3) C(9) 1.528(3) yes
C(4) C(5) 1.533(2) yes
C(4) C(11) 1.515(2) yes
C(5) C(15) 1.535(3) yes
C(6) C(7) 1.501(2) yes
C(6) C(13) 1.533(3) yes
C(6) C(14) 1.532(3) yes
C(7) C(8) 1.409(2) yes
N(8) C(16) 1.392(2) yes
