#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/97/2009725.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_2009725
loop_
_publ_author_name
'Hirota, T.'
'Sasaki, K.'
'Yamamoto, H.'
'Mori, K.'
'Kashino, S.'
_publ_section_title
;
 Anomalous products formed from
 N-(5,6-dihydrobenzo[h]quinazolin-4-yl)amidines and
 hydroxylamine hydrochloride
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              807
_journal_page_last               810
_journal_paper_doi               10.1107/S0108270193010583
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C14 H14 N4 O2'
_chemical_formula_weight         270.29
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90.
_cell_angle_beta                 96.84(4)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   8.246(6)
_cell_length_b                   11.016(3)
_cell_length_c                   14.740(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295
_cell_measurement_theta_max      11.5
_cell_measurement_theta_min      11.0
_cell_volume                     1329.4(11)
_diffrn_measurement_device       'Rigaku AFC-5R'
_diffrn_measurement_method       2θ/ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2654
_diffrn_reflns_theta_max         25.0
_diffrn_standards_decay_%        2.7
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       1.66E-6
_refine_ls_extinction_method     secondary
_refine_ls_goodness_of_fit_obs   1.43
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     238
_refine_ls_number_reflns         1649
_refine_ls_R_factor_obs          0.041
_refine_ls_shift/esd_max         0.33
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(Fₒ)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.031
_reflns_number_observed          1649
_reflns_number_total             2474
_reflns_observed_criterion       I>2.0\s(I)
_cod_data_source_file            oh1051.cif
_cod_data_source_block           oh1051_structure_1_of_2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '1/\s^2^(F~o~)' 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^(F~o~)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1329.0(10)
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               2009725
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .1902(2) .21550(10) .56525(9)
O(2) -.0575(2) .03120(10) .89240(10)
N(1) .2078(2) .0913(2) .54090(10)
N(2) .0881(2) .10510(10) .66970(10)
N(3) -.0059(2) .2335(2) .81410(10)
N(4) -.0010(2) .12620(10) .95280(10)
C(1) .0293(2) .3377(2) .76580(10)
C(2) .0897(2) .3301(2) .68420(10)
C(3) .1264(3) .4448(2) .6343(2)
C(4) .1800(3) .5458(2) .7008(2)
C(5) .0170(3) .6741(2) .7991(2)
C(6) -.0967(3) .6863(2) .8601(2)
C(7) -.1699(3) .5853(2) .8910(2)
C(8) -.1291(3) .4710(2) .86180(10)
C(9) -.0119(2) .4572(2) .80170(10)
C(10) .0601(2) .5609(2) .76890(10)
C(11) .1189(2) .2153(2) .64330(10)
C(12) .1471(3) .0332(2) .60540(10)
C(13) .0183(3) .2227(2) .90720(10)
C(14) .1441(5) -.1018(2) .6098(2)
H(02) -.050(3) -.034(2) .9300(10)
H(N3) -.008(2) .158(2) .7840(10)
H(3A) .032(2) .467(2) .5930(10)
H(3B) .216(2) .424(2) .5960(10)
H(4A) .284(2) .522(2) .7310(10)
H(4B) .191(2) .626(2) .6670(10)
H(5) .064(2) .746(2) .7740(10)
H(6) -.124(2) .770(2) .8800(10)
H(7) -.255(2) .592(2) .9310(10)
H(8) -.185(2) .398(2) .8810(10)
H(13) .054(2) .295(2) .9420(10)
H(14A) .186(3) -.134(2) .559(2)
H(14B) .031(4) -.132(2) .617(2)
H(14C) .208(3) -.131(2) .663(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(1) O(1) C(11) 106.3(2) yes
O(1) N(1) C(12) 103.3(2) yes
C(11) N(2) C(12) 103.5(2) yes
C(1) N(3) C(13) 124.5(2) yes
O(2) N(4) C(13) 109.7(2) yes
N(3) C(1) C(2) 121.3(2) yes
N(3) C(1) C(9) 118.7(2) yes
C(2) C(1) C(9) 119.9(2) yes
C(1) C(2) C(3) 119.7(2) yes
C(1) C(2) C(11) 121.7(2) yes
C(3) C(2) C(11) 118.6(2) yes
C(2) C(3) C(4) 111.1(2) yes
C(3) C(4) C(10) 110.5(2) yes
C(6) C(5) C(10) 121.1(2) yes
C(5) C(6) C(7) 119.8(2) yes
C(6) C(7) C(8) 120.2(2) yes
C(7) C(8) C(9) 120.6(2) yes
C(1) C(9) C(8) 122.1(2) yes
C(1) C(9) C(10) 118.7(2) yes
C(8) C(9) C(10) 119.0(2) yes
C(4) C(10) C(5) 122.0(2) yes
C(4) C(10) C(9) 118.8(2) yes
C(5) C(10) C(9) 119.3(2) yes
O(1) C(11) N(2) 111.9(2) yes
O(1) C(11) C(2) 117.9(2) yes
N(2) C(11) C(2) 130.2(2) yes
N(1) C(12) N(2) 115.0(2) yes
N(1) C(12) C(14) 122.4(2) yes
N(2) C(12) C(14) 122.6(2) yes
N(3) C(13) N(4) 125.9(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) N(1) 1.427(2) yes
O(1) C(11) 1.353(2) yes
O(2) N(4) 1.417(2) yes
N(1) C(12) 1.295(2) yes
N(2) C(11) 1.308(2) yes
N(2) C(12) 1.368(2) yes
N(3) C(1) 1.399(2) yes
N(3) C(13) 1.369(2) yes
N(4) C(13) 1.278(2) yes
C(1) C(2) 1.358(2) yes
C(1) C(9) 1.474(2) yes
C(2) C(3) 1.511(3) yes
C(2) C(11) 1.433(3) yes
C(3) C(4) 1.514(3) yes
C(4) C(10) 1.501(3) yes
C(5) C(6) 1.381(3) yes
C(5) C(10) 1.384(3) yes
C(6) C(7) 1.369(3) yes
C(7) C(8) 1.385(3) yes
C(8) C(9) 1.395(3) yes
C(9) C(10) 1.399(3) yes
C(12) C(14) 1.489(3) yes
O(2) H(02) 0.91(2) no
N(3) H(N3) 0.94(2) no
C(3) H(3A) 0.96(2) no
C(3) H(3B) 1.01(2) no
C(4) H(4A) 0.96(2) no
C(4) H(4B) 1.02(2) no
C(5) H(5) 0.98(2) no
C(6) H(6) 1.00(2) no
C(7) H(7) 0.97(2) no
C(8) H(8) 0.98(2) no
C(13) H(13) 0.98(2) no
C(14) H(14A) 0.93(3) no
C(14) H(14B) 1.01(3) no
C(14) H(14C) 0.94(2) no
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
O(1) N(1) C(12) N(2) 1.1(2) yes
O(1) C(11) N(2) C(12) 1.4(2) yes
N(1) O(1) C(11) N(2) -0.8(2) yes
N(1) C(12) N(2) C(11) -1.6(2) yes
C(11) O(1) N(1) C(12) -0.2(2) yes
N(3) C(1) C(9) C(8) -21.7(3) yes
C(1) C(2) C(3) C(4) 32.0(3) yes
C(1) C(9) C(10) C(4) -1.8(3) yes
C(2) C(3) C(4) C(10) -51.4(3) yes
C(3) C(2) C(1) C(9) 4.7(3) yes
C(3) C(4) C(10) C(9) 37.9(3) yes
N(2) C(11) C(2) C(3) -175.3(2) yes
O(2) N(4) C(13) N(3) -2.0(3) yes
N(4) C(13) N(3) C(1) -174.4(2) yes
C(9) C(1) N(3) C(13) -41.4(3) yes
