#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/18/2221823.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_2221823
loop_
_publ_author_name
'Kettmann, Viktor'
'Světlík, Jan'
_publ_section_title
;
 2-Methyl-1,10b-dihydro-5H-pyrazolo[1,5-c][1,3]benzoxazin-5-one
;
_journal_coeditor_code           TK2391
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o984
_journal_paper_doi               10.1107/S1600536809012173
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C11 H10 N2 O2'
_chemical_formula_moiety         'C11 H10 N2 O2'
_chemical_formula_sum            'C11 H10 N2 O2'
_chemical_formula_weight         202.21
_chemical_melting_point          433
_chemical_name_systematic
;
2-Methyl-1,10b-dihydro-5H-pyrazolo[1,5-c][1,3]benzoxazin-5-one
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.240(2)
_cell_length_b                   8.835(2)
_cell_length_c                   15.755(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      7
_cell_volume                     1007.8(4)
_computing_cell_refinement       'XSCANS (Siemens, 1991)'
_computing_data_collection       'XSCANS (Siemens, 1991)'
_computing_data_reduction        'XSCANS (Siemens, 1991)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω/2θ
_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  0.021
_diffrn_reflns_av_sigmaI/netI    0.029
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            2285
_diffrn_reflns_theta_full        30.0
_diffrn_reflns_theta_max         30.0
_diffrn_reflns_theta_min         2.6
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.22
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.96
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1674
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.96
_refine_ls_R_factor_all          0.068
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.058P)²+0.7099P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.151
_refine_ls_wR_factor_ref         0.161
_reflns_number_gt                1343
_reflns_number_total             1674
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2391.cif
_cod_data_source_block           I
_cod_database_code               2221823
_cod_database_fobs_code          2221823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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 0.1064(5) 0.4867(4) -0.11974(19) 0.0540(8) Uani d . 1 . .
H H1A 0.0197 0.5671 -0.1328 0.065 Uiso calc R 1 . .
H H1B 0.2107 0.4926 -0.1582 0.065 Uiso calc R 1 . .
C C2 0.0157(5) 0.3341(4) -0.1229(2) 0.0600(9) Uani d . 1 . .
N N3 -0.0199(4) 0.2741(3) -0.05137(18) 0.0581(7) Uani d . 1 . .
N N4 0.0479(4) 0.3750(3) 0.00991(16) 0.0484(6) Uani d . 1 . .
C C5 0.0201(5) 0.3524(4) 0.0925(2) 0.0523(8) Uani d . 1 . .
O O5 -0.0494(5) 0.2447(3) 0.12627(15) 0.0761(9) Uani d . 1 . .
O O6 0.0794(4) 0.4709(3) 0.14279(14) 0.0583(7) Uani d . 1 . .
C C6A 0.1009(4) 0.6157(3) 0.1075(2) 0.0475(7) Uani d . 1 . .
C C7 0.0800(5) 0.7370(4) 0.1622(2) 0.0594(9) Uani d . 1 . .
H H7 0.0532 0.7219 0.2193 0.071 Uiso calc R 1 . .
C C8 0.1000(6) 0.8811(4) 0.1297(3) 0.0675(11) Uani d . 1 . .
H H8 0.0873 0.9643 0.1654 0.081 Uiso calc R 1 . .
C C9 0.1389(5) 0.9035(4) 0.0445(3) 0.0669(11) Uani d . 1 . .
H H9 0.1507 1.0011 0.0230 0.080 Uiso calc R 1 . .
C C10 0.1601(5) 0.7788(4) -0.0086(3) 0.0569(8) Uani d . 1 . .
H H10 0.1858 0.7931 -0.0659 0.068 Uiso calc R 1 . .
C C10A 0.1430(4) 0.6339(3) 0.0233(2) 0.0431(6) Uani d . 1 . .
C C10B 0.1680(5) 0.4926(3) -0.02737(18) 0.0429(6) Uani d . 1 . .
H H10B 0.2971 0.4598 -0.0235 0.051 Uiso calc R 1 . .
C C11 -0.0392(8) 0.2580(7) -0.2042(3) 0.0990(19) Uani d . 1 . .
H H11A -0.0912 0.1605 -0.1918 0.149 Uiso calc R 1 . .
H H11B 0.0677 0.2458 -0.2396 0.149 Uiso calc R 1 . .
H H11C -0.1290 0.3190 -0.2331 0.149 Uiso calc R 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 for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
H H 0.0000 0.0000
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
N N 0.0061 0.0033
; International Tables for Crystallography (1992).
Vol. C, Tables 4.2.6.8 and 6.1.1.4
;
O O 0.0106 0.0060
; International Tables for Crystallography (1992).
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 C10B . . 101.0(3) ?
C2 C1 H1A . . 111.6 ?
C10B C1 H1A . . 111.6 ?
C2 C1 H1B . . 111.6 ?
C10B C1 H1B . . 111.6 ?
H1A C1 H1B . . 109.4 ?
N3 C2 C1 . . 115.7(3) ?
N3 C2 C11 . . 121.1(4) ?
C1 C2 C11 . . 123.2(3) ?
C2 N3 N4 . . 105.9(3) ?
C5 N4 N3 . . 121.6(3) ?
C5 N4 C10B . . 125.7(3) ?
N3 N4 C10B . . 112.3(2) ?
O5 C5 N4 . . 127.9(3) ?
O5 C5 O6 . . 118.5(3) ?
N4 C5 O6 . . 113.6(3) ?
C5 O6 C6A . . 119.9(2) ?
C10A C6A C7 . . 122.4(3) ?
C10A C6A O6 . . 121.0(3) ?
C7 C6A O6 . . 116.6(3) ?
C8 C7 C6A . . 118.2(4) ?
C8 C7 H7 . . 120.9 ?
C6A C7 H7 . . 120.9 ?
C7 C8 C9 . . 120.8(3) ?
C7 C8 H8 . . 119.6 ?
C9 C8 H8 . . 119.6 ?
C8 C9 C10 . . 119.5(3) ?
C8 C9 H9 . . 120.3 ?
C10 C9 H9 . . 120.3 ?
C10A C10 C9 . . 120.3(3) ?
C10A C10 H10 . . 119.8 ?
C9 C10 H10 . . 119.8 ?
C6A C10A C10 . . 118.8(3) ?
C6A C10A C10B . . 116.5(3) ?
C10 C10A C10B . . 124.7(3) ?
N4 C10B C10A . . 107.7(2) ?
N4 C10B C1 . . 100.6(3) ?
C10A C10B C1 . . 120.3(3) ?
N4 C10B H10B . . 109.2 ?
C10A C10B H10B . . 109.2 ?
C1 C10B H10B . . 109.2 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
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 . 1.501(5) ?
C1 C10B . 1.523(4) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 N3 . 1.272(4) ?
C2 C11 . 1.499(5) ?
N3 N4 . 1.403(4) ?
N4 C5 . 1.332(4) ?
N4 C10B . 1.477(4) ?
C5 O5 . 1.200(4) ?
C5 O6 . 1.381(4) ?
O6 C6A . 1.404(4) ?
C6A C10A . 1.371(4) ?
C6A C7 . 1.383(4) ?
C7 C8 . 1.380(5) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.385(6) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.393(5) ?
C9 H9 . 0.9300 ?
C10 C10A . 1.381(4) ?
C10 H10 . 0.9300 ?
C10A C10B . 1.493(4) ?
C10B H10B . 0.9800 ?
C11 H11A . 0.9600 ?
C11 H11B . 0.9600 ?
C11 H11C . 0.9600 ?
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
C10B C1 C2 N3 . . . . 14.6(4) ?
C10B C1 C2 C11 . . . . -168.2(4) ?
C1 C2 N3 N4 . . . . -2.2(4) ?
C11 C2 N3 N4 . . . . -179.4(4) ?
C2 N3 N4 C5 . . . . 174.6(4) ?
C2 N3 N4 C10B . . . . -12.4(4) ?
N3 N4 C5 O5 . . . . 5.9(7) ?
C10B N4 C5 O5 . . . . -166.1(4) ?
N3 N4 C5 O6 . . . . -173.5(3) ?
C10B N4 C5 O6 . . . . 14.4(5) ?
O5 C5 O6 C6A . . . . -158.0(4) ?
N4 C5 O6 C6A . . . . 21.5(5) ?
C5 O6 C6A C10A . . . . -28.5(5) ?
C5 O6 C6A C7 . . . . 152.4(3) ?
C10A C6A C7 C8 . . . . 1.0(5) ?
O6 C6A C7 C8 . . . . -180.0(3) ?
C6A C7 C8 C9 . . . . 0.4(6) ?
C7 C8 C9 C10 . . . . -0.8(6) ?
C8 C9 C10 C10A . . . . -0.2(6) ?
C7 C6A C10A C10 . . . . -1.9(5) ?
O6 C6A C10A C10 . . . . 179.1(3) ?
C7 C6A C10A C10B . . . . 177.9(3) ?
O6 C6A C10A C10B . . . . -1.2(4) ?
C9 C10 C10A C6A . . . . 1.5(5) ?
C9 C10 C10A C10B . . . . -178.3(3) ?
C5 N4 C10B C10A . . . . -40.0(4) ?
N3 N4 C10B C10A . . . . 147.3(3) ?
C5 N4 C10B C1 . . . . -166.7(3) ?
N3 N4 C10B C1 . . . . 20.6(3) ?
C6A C10A C10B N4 . . . . 30.5(4) ?
C10 C10A C10B N4 . . . . -149.8(3) ?
C6A C10A C10B C1 . . . . 144.7(3) ?
C10 C10A C10B C1 . . . . -35.6(5) ?
C2 C1 C10B N4 . . . . -19.1(3) ?
C2 C1 C10B C10A . . . . -137.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 26000968
