#------------------------------------------------------------------------------
#$Date: 2020-04-10 08:22:27 +0300 (Fri, 10 Apr 2020) $
#$Revision: 250629 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022050.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_2022050
loop_
_publ_author_name
'Jha, Kunal Kumar'
'Gruza, Barbara'
'Kumar, Prashant'
'Chodkiewicz, Michal Leszek'
'Dominiak, Paulina Maria'
_publ_section_title
;
 TAAM: a reliable and user friendly tool for hydrogen-atom location using
 routine X-ray diffraction data
;
_journal_issue                   3
_journal_name_full
'Acta Crystallographica Section B Structural Science, Crystal Engineering and Materials'
_journal_paper_doi               10.1107/S2052520620002917
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C8 H8 N2 O2'
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_weight         164.16
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_audit_creation_date             2019-09-23
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                116.823(8)
_cell_angle_beta                 104.589(9)
_cell_angle_gamma                91.602(5)
_cell_formula_units_Z            2
_cell_length_a                   5.7913(3)
_cell_length_b                   8.2458(6)
_cell_length_c                   8.9223(10)
_cell_measurement_temperature    90.00(10)
_cell_volume                     362.99(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      90.00(10)
_diffrn_measured_fraction_theta_full 0.6214
_diffrn_measured_fraction_theta_max 0.6214
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur System'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            8768
_diffrn_reflns_theta_full        70.1931
_diffrn_reflns_theta_max         70.19
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.111
_exptl_crystal_density_diffrn    1.5019
_exptl_crystal_F_000             172.0904
_refine_diff_density_max         0.4856
_refine_diff_density_min         -0.3581
_refine_diff_density_rms         0.0460
_refine_ls_d_res_high            0.3777
_refine_ls_d_res_low             7.2590
_refine_ls_goodness_of_fit_ref   1.3413
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     141
_refine_ls_number_reflns         8768
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.3413
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0249
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0229P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0569
_refine_ls_wR_factor_ref         0.0579
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              -21
_reflns_limit_l_max              23
_reflns_limit_l_min              0
_reflns_number_gt                7933
_reflns_number_total             8768
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            2_TAAM_iso_max.cif
_cod_data_source_block           2_TAAM_iso_max
_cod_original_cell_volume        362.990(50)
_cod_database_code               2022050
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
O1 O 0.78210(3) 1.08676(3) 0.27352(3) 0.01889(3) Uani 1.000000 .
O2 O 1.11906(4) 1.13966(2) 0.48228(2) 0.01841(3) Uani 1.000000 .
N1 N 1.06733(3) 0.90146(2) 0.22098(2) 0.01318(2) Uani 1.000000 .
N2 N 0.98492(3) 1.05042(2) 0.33010(2) 0.01373(2) Uani 1.000000 .
C1 C 0.96752(3) 0.79787(2) 0.03615(2) 0.01069(2) Uani 1.000000 .
C2 C 1.12756(3) 0.67053(2) -0.02715(2) 0.01079(2) Uani 1.000000 .
C3 C 1.07494(4) 0.54986(3) -0.20614(2) 0.01398(3) Uani 1.000000 .
H3 H 1.1939(11) 0.4506(9) -0.2592(8) 0.0343(14) Uiso 1.000000 .
C4 C 0.86132(4) 0.55760(3) -0.32111(3) 0.01577(3) Uani 1.000000 .
H4 H 0.8204(11) 0.4623(9) -0.4598(9) 0.0376(15) Uiso 1.000000 .
C5 C 0.70386(4) 0.68537(3) -0.25614(3) 0.01536(3) Uani 1.000000 .
H5 H 0.5374(11) 0.6924(8) -0.3422(8) 0.0315(14) Uiso 1.000000 .
C6 C 0.75368(3) 0.80815(3) -0.07581(3) 0.01370(3) Uani 1.000000 .
H6 H 0.6323(10) 0.9035(8) -0.0251(7) 0.0282(13) Uiso 1.000000 .
C8 C 1.34205(3) 0.68716(3) 0.12125(2) 0.01270(2) Uani 1.000000 .
H8a H 1.3410(10) 0.5653(8) 0.1375(7) 0.0276(13) Uiso 1.000000 .
H8b H 1.5122(11) 0.7031(8) 0.0984(8) 0.0337(14) Uiso 1.000000 .
C7 C 1.30983(4) 0.85643(3) 0.28537(2) 0.01391(3) Uani 1.000000 .
H7a H 1.4386(11) 0.9740(9) 0.3316(8) 0.0350(15) Uiso 1.000000 .
H7b H 1.3083(10) 0.8253(8) 0.3913(8) 0.0353(15) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C C 0.00347 0.00161
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H H 0.00000 0.00000
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N N 0.00653 0.00323
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O O 0.01158 0.00611
'Clementi & Roetti, C., At. Data Nucl. Data Tables 1974, 14, (177-478); Clementi & Raimondi, J. Chem. Phys., 1963, 38, (2686-2689)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 125.970(17) . . ?
C7 N1 N2 120.756(16) . . ?
C7 N1 C1 112.169(15) . . ?
O2 N2 O1 124.321(18) . . ?
N1 N2 O1 119.866(18) . . ?
N1 N2 O2 115.802(18) . . ?
C2 C1 N1 107.204(14) . . ?
C6 C1 N1 129.794(17) . . ?
C6 C1 C2 123.001(16) . . ?
C3 C2 C1 120.022(16) . . ?
C8 C2 C1 112.109(14) . . ?
C8 C2 C3 127.865(17) . . ?
H3 C3 C2 121.9(3) . . ?
C4 C3 C2 118.010(18) . . ?
C4 C3 H3 120.1(3) . . ?
H4 C4 C3 117.6(3) . . ?
C5 C4 C3 121.329(17) . . ?
C5 C4 H4 121.1(3) . . ?
H5 C5 C4 122.5(3) . . ?
C6 C5 C4 121.510(17) . . ?
C6 C5 H5 116.0(3) . . ?
C5 C6 C1 116.127(18) . . ?
H6 C6 C1 122.0(3) . . ?
H6 C6 C5 121.9(3) . . ?
H8a C8 C2 112.6(3) . . ?
H8b C8 C2 112.9(3) . . ?
H8b C8 H8a 103.9(4) . . ?
C7 C8 C2 102.914(14) . . ?
C7 C8 H8a 111.4(3) . . ?
C7 C8 H8b 113.5(3) . . ?
C8 C7 N1 104.917(14) . . ?
H7a C7 N1 106.8(3) . . ?
H7a C7 C8 112.8(3) . . ?
H7b C7 N1 108.9(3) . . ?
H7b C7 C8 112.5(3) . . ?
H7b C7 H7a 110.6(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N2 1.2577(3) . ?
O2 N2 1.2343(2) . ?
N1 N2 1.3682(2) . ?
N1 C1 1.4157(2) . ?
N1 C7 1.5018(3) . ?
C1 C2 1.4365(2) . ?
C1 C6 1.4135(3) . ?
C2 C3 1.3918(2) . ?
C2 C8 1.5208(2) . ?
C3 H3 1.102(6) . ?
C3 C4 1.4181(3) . ?
C4 H4 1.082(7) . ?
C4 C5 1.4306(3) . ?
C5 H5 1.092(6) . ?
C5 C6 1.4060(3) . ?
C6 H6 1.090(6) . ?
C8 H8a 1.078(6) . ?
C8 H8b 1.072(6) . ?
C8 C7 1.5604(3) . ?
C7 H7a 1.054(6) . ?
C7 H7b 1.087(6) . ?
