#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/41/2004117.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_2004117
loop_
_publ_author_name
'Brock, C. P.'
'Demir, A. S.'
'Watt, D. S.'
_publ_section_title
;
 An Almost Planar Hydrazine Moiety in a Diels--Alder Adduct
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2434
_journal_page_last               2437
_journal_paper_doi               10.1107/S010827019500624X
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C16 H17 N3 O2'
_chemical_formula_sum            'C16 H17 N3 O2'
_chemical_formula_weight         283.33
_chemical_melting_point          295.0(10)
_chemical_name_systematic
;
4-phenyl-2,4,6-triazatricyclo[5.4.2.0^2,6^]tridec-12-ene-3,5-dione
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 91.207(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3828(7)
_cell_length_b                   12.2813(7)
_cell_length_c                   10.9310(9)
_cell_measurement_reflns_used    19
_cell_measurement_temperature    295.0(10)
_cell_measurement_theta_max      12.9
_cell_measurement_theta_min      12.3
_cell_volume                     1393.55(17)
_computing_cell_refinement       CAD-4
_computing_data_collection       'CAD-4 (Enraf-Nonius, 1988)'
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXTL/PC (Sheldrick, 1990)'
_diffrn_ambient_temperature      295.0(10)
_diffrn_measurement_device       'ENRAF-Nonius CAD4-VAX diffractometer'
_diffrn_measurement_method       'ω/2θ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_sigmaI/netI    0.0607
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2449
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        0.6
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_type   'empirical, eight \y scans (Flack, 1977)'
_exptl_absorpt_process_details   'based on eight psi scans'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_description
;
Tablets: major faces are {10\=1}, {11\=1}, {010}, {111}, {101}
;
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.216
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.016
_refine_ls_goodness_of_fit_obs   1.113
_refine_ls_hydrogen_treatment    'H atoms riding'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.023
_refine_ls_restrained_S_obs      1.121
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_obs          0.0415
_refine_ls_shift/esd_max         -0.012
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0589P)²+0.1185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1181
_refine_ls_wR_factor_obs         0.0950
_reflns_number_observed          1412
_reflns_number_total             2449
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cr1189.cif
_cod_data_source_block           asdiii28
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.1185P] 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^)+(0.0589P)^2^+0.1185P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1393.54(17)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2004117
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_type_symbol
O1 1 .0504(2) .22120(14) .04501(14) .0597(5) Uani d . . O
O2 1 -.0115(2) .29088(14) -0.36598(14) .0563(5) Uani d . . O
N1 1 .1511(2) .3316(2) -.0931(2) .0570(6) Uani d . . N
N2 1 -.0164(2) .24111(15) -0.1592(2) .0424(5) Uani d . . N
N3 1 .1324(2) .3524(2) -0.2186(2) .0560(6) Uani d . . N
C1 1 .2716(2) .3601(2) -.0305(2) .0492(6) Uani d . . C
H1 1 .2857(2) .3081(2) .0364(2) .059 Uiso calc R . H
C2 1 .0621(2) .2597(2) -.0564(2) .0451(6) Uani d . . C
C3 1 .0308(2) .2945(2) -0.2617(2) .0446(6) Uani d . . C
C4 1 .2355(2) .4032(2) -0.2868(2) .0515(6) Uani d . . C
H4 1 .2290(2) .3773(2) -0.3716(2) .062 Uiso calc R . H
C5 1 .3625(2) .3678(2) -0.2347(2) .0576(7) Uani d . . C
H5 1 .4317(2) .3595(2) -0.2865(2) .069 Uiso calc R . H
C6 1 .3792(2) .3479(2) -0.1170(3) .0587(7) Uani d . . C
H6 1 .4598(2) .3259(2) -.0875(3) .070 Uiso calc R . H
C7 1 .2194(3) .5269(2) -0.2880(2) .0595(7) Uani d D . C
H7A 1 .1526(3) .5454(2) -0.3477(2) .071 Uiso calc R 1 H
H7B 1 .2991(3) .5591(2) -0.3154(2) .071 Uiso calc R 1 H
C81 .746(7) .1849(5) .5796(3) -0.1646(4) .0677(14) Uani d P 1 C
H81A .746(7) .1688(5) .6564(3) -0.1787(4) .081 Uiso calc PR 1 H
H81B .746(7) .1050(5) .5475(3) -0.1377(4) .081 Uiso calc PR 1 H
C91 .746(7) .2837(5) .5693(3) -.0616(4) .071(2) Uani d P 1 C
H91A .746(7) .2823(5) .6358(3) -.0138(4) .086 Uiso calc PR 1 H
H91B .746(7) .3683(5) .5638(3) -.0971(4) .086 Uiso calc PR 1 H
C82 .254(7) .2675(13) .5861(9) -0.1774(8) .060(4) Uiso d PD 2 C
H82A .254(7) .2600(13) .6638(9) -0.1914(8) .072 Uiso calc PR 2 H
H82B .254(7) .3580(13) .5694(9) -0.1639(8) .072 Uiso calc PR 2 H
C92 .254(7) .1929(12) .5558(10) -.0618(10) .073(4) Uiso d PD 2 C
H92A .254(7) .1108(12) .5240(10) -.0864(10) .088 Uiso calc PR 2 H
H92B .254(7) .1751(12) .6217(10) -.0163(10) .088 Uiso calc PR 2 H
C10 1 .2667(3) .4736(2) .0248(2) .0649(8) Uani d D . C
H10A 1 .3330(3) .4782(2) .0884(2) .078 Uiso calc R 1 H
H10B 1 .1843(3) .4818(2) .0641(2) .078 Uiso calc R 1 H
C21 1 -0.1277(2) .1726(2) -0.1589(2) .0398(5) Uani d . . C
C22 1 -0.1164(2) .0664(2) -0.1211(2) .0466(6) Uani d . . C
H22 1 -.0361(2) .0383(2) -.0988(2) .056 Uiso calc R . H
C23 1 -0.2244(2) .0017(2) -0.1162(2) .0534(6) Uani d . . C
H23 1 -0.2169(2) -.0704(2) -.0908(2) .064 Uiso calc R . H
C24 1 -0.3424(2) .0430(2) -0.1485(2) .0581(7) Uani d . . C
H24 1 -0.4156(2) -.0003(2) -0.1430(2) .070 Uiso calc R . H
C25 1 -0.3528(2) .1486(2) -0.1891(2) .0605(7) Uani d . . C
H25 1 -0.4328(2) .1759(2) -0.2136(2) .073 Uiso calc R . H
C26 1 -0.2458(2) .2140(2) -0.1936(2) .0513(6) Uani d . . C
H26 1 -0.2532(2) .2858(2) -0.2199(2) .062 Uiso calc R . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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
_geom_angle_publ_flag
C2 N1 N3 109.2(2) yes
C2 N1 C1 127.4(2) yes
N3 N1 C1 121.0(2) yes
C2 N2 C3 111.1(2) yes
C2 N2 C21 123.7(2) yes
C3 N2 C21 125.1(2) yes
C3 N3 N1 109.6(2) yes
C3 N3 C4 128.7(2) yes
N1 N3 C4 119.3(2) yes
N1 C1 C6 109.1(2) yes
N1 C1 C10 111.8(2) yes
C6 C1 C10 112.2(2) yes
O1 C2 N1 127.6(2) yes
O1 C2 N2 127.2(2) yes
N1 C2 N2 105.2(2) yes
O2 C3 N3 127.7(2) yes
O2 C3 N2 127.6(2) yes
N3 C3 N2 104.7(2) yes
N3 C4 C5 109.5(2) yes
N3 C4 C7 110.4(2) yes
C5 C4 C7 112.8(2) yes
C6 C5 C4 121.7(2) yes
C5 C6 C1 121.1(2) yes
C82 C7 C4 116.4(5) yes
C4 C7 C81 115.9(2) yes
C91 C81 C7 116.7(4) yes
C81 C91 C10 116.2(4) yes
C7 C82 C92 112.5(10) yes
C82 C92 C10 113.7(9) yes
C1 C10 C91 117.1(2) yes
C1 C10 C92 111.7(6) yes
C22 C21 C26 120.3(2) yes
C22 C21 N2 119.8(2) yes
C26 C21 N2 119.9(2) yes
C21 C22 C23 119.8(2) yes
C24 C23 C22 120.1(2) yes
C23 C24 C25 119.9(2) yes
C24 C25 C26 120.3(2) yes
C21 C26 C25 119.5(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.214(3) yes
O2 C3 1.214(3) yes
N1 C2 1.344(3) yes
N1 N3 1.406(2) yes
N1 C1 1.456(3) yes
N2 C2 1.393(3) yes
N2 C3 1.396(3) yes
N2 C21 1.429(3) yes
N3 C3 1.348(3) yes
N3 C4 1.457(3) yes
C1 C6 1.487(3) yes
C1 C10 1.520(3) yes
C4 C5 1.491(3) yes
C4 C7 1.529(3) yes
C5 C6 1.317(3) yes
C7 C82 1.488(9) yes
C7 C81 1.544(5) yes
C81 C91 1.513(6) yes
C91 C10 1.521(5) yes
C82 C92 1.542(12) yes
C92 C10 1.572(9) yes
C21 C22 1.373(3) yes
C21 C26 1.373(3) yes
C22 C23 1.376(3) yes
C23 C24 1.366(3) yes
C24 C25 1.374(4) yes
C25 C26 1.374(3) yes
