#------------------------------------------------------------------------------
#$Date: 2020-04-10 08:23:18 +0300 (Fri, 10 Apr 2020) $
#$Revision: 250631 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022052.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_2022052
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         'C6 H6 N12 O12'
_chemical_formula_sum            'C6 H6 N12 O12'
_chemical_formula_weight         438.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_audit_creation_date             2019-09-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.5780(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7890(10)
_cell_length_b                   12.4740(10)
_cell_length_c                   13.2790(10)
_cell_measurement_temperature    100
_cell_volume                     1395.3(2)
_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      100
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_device_type  'Beamline E2; HASYLAB DESY'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.503
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15978
_diffrn_reflns_theta_full        26.4981
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.200
_exptl_crystal_density_diffrn    2.0858
_exptl_crystal_F_000             888.6445
_refine_diff_density_max         0.1587
_refine_diff_density_min         -0.3196
_refine_diff_density_rms         0.0493
_refine_ls_d_res_high            0.7965
_refine_ls_d_res_low             8.9086
_refine_ls_goodness_of_fit_ref   1.0718
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     325
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0718
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0227P)²+0.3818P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0506
_refine_ls_wR_factor_ref         0.0509
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                2825
_reflns_number_total             2890
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            13_TAAM_ANIS_0.8.cif
_cod_data_source_block           13_TAAM_ANIS_0.8
_cod_original_cell_volume        1395.3140(10)
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               2022052
_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+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2
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
O(1) O -0.09028(8) 0.61237(5) 0.35496(6) 0.02044(15) Uani 1.000000 .
O(2) O -0.26288(7) 0.72380(5) 0.38315(5) 0.01508(13) Uani 1.000000 .
O(3) O -0.34814(7) 0.73650(5) 0.15047(5) 0.01485(13) Uani 1.000000 .
O(4) O -0.29000(7) 0.79819(5) 0.01276(4) 0.01597(13) Uani 1.000000 .
O(5) O 0.07966(7) 1.11263(5) 0.11141(4) 0.01349(13) Uani 1.000000 .
O(6) O 0.09776(7) 1.16050(5) 0.27187(4) 0.01238(12) Uani 1.000000 .
O(7) O 0.30825(8) 0.94558(5) 0.51087(5) 0.02074(14) Uani 1.000000 .
O(8) O 0.12393(7) 1.06461(5) 0.49092(5) 0.01472(13) Uani 1.000000 .
O(9) O 0.46280(7) 0.88256(5) 0.27377(5) 0.01585(13) Uani 1.000000 .
O(10 O 0.35061(8) 0.90225(5) 0.10664(5) 0.02005(14) Uani 1.000000 .
O(11 O 0.09740(8) 0.67834(5) 0.04033(5) 0.01713(14) Uani 1.000000 .
O(12 O 0.09699(7) 0.58551(5) 0.17815(5) 0.01522(13) Uani 1.000000 .
N(1) N -0.14838(8) 0.70033(6) 0.35471(5) 0.01216(14) Uani 1.000000 .
N(2) N -0.06931(8) 0.78637(5) 0.32211(5) 0.00977(14) Uani 1.000000 .
N(3) N -0.28708(8) 0.80004(6) 0.10498(5) 0.01081(14) Uani 1.000000 .
N(4) N -0.20852(8) 0.88579(5) 0.16268(5) 0.00934(14) Uani 1.000000 .
N(5) N 0.04953(8) 1.10373(5) 0.19531(5) 0.00980(14) Uani 1.000000 .
N(6) N -0.05261(8) 1.02324(5) 0.20316(5) 0.00911(14) Uani 1.000000 .
N(7) N 0.18711(8) 0.98870(6) 0.46226(5) 0.01162(14) Uani 1.000000 .
N(8) N 0.11047(8) 0.94579(5) 0.36425(5) 0.01024(14) Uani 1.000000 .
N(9) N 0.35041(8) 0.89287(5) 0.19731(6) 0.01225(14) Uani 1.000000 .
N(10 N 0.19829(8) 0.90285(5) 0.21586(5) 0.00942(14) Uani 1.000000 .
N(11 N 0.08111(8) 0.66678(5) 0.12674(5) 0.01149(14) Uani 1.000000 .
N(12 N 0.02697(8) 0.75802(5) 0.17109(5) 0.00903(14) Uani 1.000000 .
C(1) C 0.06814(9) 0.76375(6) 0.28698(6) 0.00926(15) Uani 1.000000 .
H(1) H 0.1216(16) 0.6908(11) 0.3211(10) 0.031(3) Uani 1.000000 .
C(3) C -0.16052(9) 0.88082(6) 0.27892(6) 0.00920(15) Uani 1.000000 .
H(3) H -0.2604(15) 0.8859(10) 0.3098(10) 0.028(3) Uani 1.000000 .
C(5) C -0.08676(9) 0.93831(6) 0.12514(6) 0.00919(15) Uani 1.000000 .
H(5) H -0.1336(15) 0.9692(11) 0.0474(10) 0.031(3) Uani 1.000000 .
C(7) C -0.04675(9) 0.98137(6) 0.30795(6) 0.00913(15) Uani 1.000000 .
H(7) H -0.0880(14) 1.0376(10) 0.3523(9) 0.023(3) Uani 1.000000 .
C(9) C 0.18363(9) 0.86333(6) 0.31729(6) 0.00940(15) Uani 1.000000 .
H(9) H 0.2929(16) 0.8423(10) 0.3684(11) 0.031(3) Uani 1.000000 .
C(11 C 0.06221(9) 0.86238(6) 0.13294(6) 0.00905(15) Uani 1.000000 .
H(11 H 0.0877(15) 0.8560(11) 0.0606(10) 0.031(3) Uani 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
O(2) N(1) O(1) 127.43(7) . . ?
N(2) N(1) O(1) 116.48(7) . . ?
N(2) N(1) O(2) 116.01(7) . . ?
C(1) N(2) N(1) 118.79(6) . . ?
C(3) N(2) N(1) 118.33(6) . . ?
C(3) N(2) C(1) 116.84(6) . . ?
O(4) N(3) O(3) 127.17(7) . . ?
N(4) N(3) O(3) 116.93(6) . . ?
N(4) N(3) O(4) 115.88(7) . . ?
C(3) N(4) N(3) 119.65(6) . . ?
C(5) N(4) N(3) 117.25(6) . . ?
C(5) N(4) C(3) 110.88(6) . . ?
O(6) N(5) O(5) 126.66(7) . . ?
N(6) N(5) O(5) 116.94(6) . . ?
N(6) N(5) O(6) 116.37(6) . . ?
C(5) N(6) N(5) 119.13(6) . . ?
C(7) N(6) N(5) 118.97(6) . . ?
C(7) N(6) C(5) 111.08(6) . . ?
O(8) N(7) O(7) 126.52(7) . . ?
N(8) N(7) O(7) 116.64(7) . . ?
N(8) N(7) O(8) 116.83(7) . . ?
C(7) N(8) N(7) 120.25(6) . . ?
C(9) N(8) N(7) 121.42(6) . . ?
C(9) N(8) C(7) 118.31(6) . . ?
O(10 N(9) O(9) 127.97(7) . . ?
N(10 N(9) O(9) 116.46(7) . . ?
N(10 N(9) O(10 115.41(7) . . ?
C(9) N(10 N(9) 117.21(6) . . ?
C(11 N(10 N(9) 116.27(6) . . ?
C(11 N(10 C(9) 107.83(6) . . ?
O(12 N(11 O(11 127.79(7) . . ?
N(12 N(11 O(11 116.27(6) . . ?
N(12 N(11 O(12 115.81(6) . . ?
C(1) N(12 N(11 117.23(6) . . ?
C(11 N(12 N(11 116.07(6) . . ?
C(11 N(12 C(1) 107.73(6) . . ?
N(12 C(1) N(2) 111.56(6) . . ?
H(1) C(1) N(2) 109.8(7) . . ?
H(1) C(1) N(12 110.4(7) . . ?
C(9) C(1) N(2) 107.46(6) . . ?
C(9) C(1) N(12 104.56(6) . . ?
C(9) C(1) H(1) 113.0(7) . . ?
N(4) C(3) N(2) 114.06(6) . . ?
H(3) C(3) N(2) 108.5(7) . . ?
H(3) C(3) N(4) 112.1(7) . . ?
C(7) C(3) N(2) 107.97(6) . . ?
C(7) C(3) N(4) 101.13(6) . . ?
C(7) C(3) H(3) 112.9(7) . . ?
N(6) C(5) N(4) 96.10(6) . . ?
H(5) C(5) N(4) 112.0(7) . . ?
H(5) C(5) N(6) 111.8(7) . . ?
C(11 C(5) N(4) 112.32(6) . . ?
C(11 C(5) N(6) 112.84(6) . . ?
C(11 C(5) H(5) 111.1(7) . . ?
N(8) C(7) N(6) 111.66(6) . . ?
C(3) C(7) N(6) 101.63(6) . . ?
C(3) C(7) N(8) 109.16(6) . . ?
H(7) C(7) N(6) 111.7(7) . . ?
H(7) C(7) N(8) 110.5(6) . . ?
H(7) C(7) C(3) 111.9(7) . . ?
N(10 C(9) N(8) 108.77(6) . . ?
C(1) C(9) N(8) 109.66(6) . . ?
C(1) C(9) N(10 104.32(6) . . ?
H(9) C(9) N(8) 109.9(7) . . ?
H(9) C(9) N(10 112.1(7) . . ?
H(9) C(9) C(1) 112.0(7) . . ?
N(12 C(11 N(10 104.75(6) . . ?
C(5) C(11 N(10 108.85(6) . . ?
C(5) C(11 N(12 107.46(6) . . ?
H(11 C(11 N(10 111.9(7) . . ?
H(11 C(11 N(12 111.8(8) . . ?
H(11 C(11 C(5) 111.8(7) . . ?
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
O(1) N(1) 1.2099(10) . ?
O(2) N(1) 1.2074(9) . ?
O(3) N(3) 1.2109(9) . ?
O(4) N(3) 1.2177(9) . ?
O(5) N(5) 1.2215(9) . ?
O(6) N(5) 1.2119(9) . ?
O(7) N(7) 1.2030(10) . ?
O(8) N(7) 1.2126(10) . ?
O(9) N(9) 1.2045(10) . ?
O(10 N(9) 1.2102(10) . ?
O(11 N(11 1.2048(9) . ?
O(12 N(11 1.2078(9) . ?
N(1) N(2) 1.4121(9) . ?
N(2) C(1) 1.4416(10) . ?
N(2) C(3) 1.4482(10) . ?
N(3) N(4) 1.3806(9) . ?
N(4) C(3) 1.4808(10) . ?
N(4) C(5) 1.4585(10) . ?
N(5) N(6) 1.3705(9) . ?
N(6) C(5) 1.4520(10) . ?
N(6) C(7) 1.4734(10) . ?
N(7) N(8) 1.3906(9) . ?
N(8) C(7) 1.4408(10) . ?
N(8) C(9) 1.4455(10) . ?
N(9) N(10 1.4324(9) . ?
N(10 C(9) 1.4739(10) . ?
N(10 C(11 1.4650(10) . ?
N(11 N(12 1.4243(9) . ?
N(12 C(1) 1.4786(9) . ?
N(12 C(11 1.4618(10) . ?
C(1) H(1) 1.065(14) . ?
C(1) C(9) 1.5818(11) . ?
C(3) H(3) 1.072(13) . ?
C(3) C(7) 1.5817(10) . ?
C(5) H(5) 1.068(13) . ?
C(5) C(11 1.5953(10) . ?
C(7) H(7) 1.045(12) . ?
C(9) H(9) 1.039(13) . ?
C(11 H(11 1.049(13) . ?
