#------------------------------------------------------------------------------
#$Date: 2020-04-10 08:30:08 +0300 (Fri, 10 Apr 2020) $
#$Revision: 250643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/20/2022064.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_2022064
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_absolute_configuration unk
_chemical_formula_moiety         'C12 H19 N5 O4, C3 H8 O, H2 O'
_chemical_formula_sum            'C15 H29 N5 O6'
_chemical_formula_weight         375.43
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_audit_creation_date             2019-09-26
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.49(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.741(2)
_cell_length_b                   9.420(2)
_cell_length_c                   11.989(2)
_cell_measurement_temperature    100
_cell_volume                     982.6(4)
_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 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_device_type  'κ axis MarCCD 165 detector'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.5600(2)
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13235
_diffrn_reflns_theta_full        20.4960
_diffrn_reflns_theta_max         20.50
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.060
_exptl_crystal_density_diffrn    1.2687
_exptl_crystal_F_000             404.0654
_refine_diff_density_max         0.0595
_refine_diff_density_min         -0.1302
_refine_diff_density_rms         0.0162
_refine_ls_d_res_high            0.7997
_refine_ls_d_res_low             7.3941
_refine_ls_goodness_of_fit_ref   1.2508
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     496
_refine_ls_number_reflns         2126
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.2508
_refine_ls_R_factor_all          0.0106
_refine_ls_R_factor_gt           0.0106
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0181P)²+0.0105P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0274
_refine_ls_wR_factor_ref         0.0274
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2119
_reflns_number_total             2126
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            32_TAAM_ANIS_0.8.cif
_cod_data_source_block           32_TAAM_ANIS_0.8
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               2022064
_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+1/2,-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
O(1) O 0.93301(6) -0.19162(5) 0.50603(4) 0.01644(10) Uani 1.000000 .
O(2) O 1.04587(6) 0.16917(6) 0.23873(4) 0.02001(11) Uani 1.000000 .
O(3) O 0.91887(5) 0.05926(6) -0.08480(4) 0.01787(11) Uani 1.000000 .
O(4) O 1.11841(5) 0.20514(5) -0.09659(4) 0.01705(11) Uani 1.000000 .
N(1) N 0.89019(7) -0.04559(7) 0.69946(5) 0.01275(11) Uani 1.000000 .
H(1a H 0.7753(16) -0.0209(15) 0.6662(10) 0.033(3) Uani 1.000000 .
H(1b H 0.9038(15) -0.1530(18) 0.7081(10) 0.031(3) Uani 1.000000 .
H(1c H 0.9070(16) 0.0035(16) 0.7825(13) 0.042(4) Uani 1.000000 .
N(2) N 0.96414(6) 0.01875(6) 0.41689(4) 0.01101(11) Uani 1.000000 .
H(2) H 0.9905(12) 0.1228(15) 0.4233(9) 0.027(3) Uani 1.000000 .
N(3) N 1.04648(7) -0.02967(7) 0.13042(4) 0.01282(11) Uani 1.000000 .
H(3) H 1.0091(12) -0.1295(14) 0.1227(8) 0.025(3) Uani 1.000000 .
N(4) N 0.61007(6) 0.13651(6) 0.35722(5) 0.01553(12) Uani 1.000000 .
N(5) N 0.50552(7) 0.24191(7) 0.20171(5) 0.01836(13) Uani 1.000000 .
H(5) H 0.4378(14) 0.3075(15) 0.1478(11) 0.037(3) Uani 1.000000 .
C(1) C 0.99974(7) 0.01263(7) 0.62194(5) 0.01230(13) Uani 1.000000 .
H(1) H 0.9793(13) 0.1278(13) 0.6131(9) 0.031(3) Uani 1.000000 .
C(2) C 0.96211(7) -0.06233(7) 0.50889(5) 0.01126(12) Uani 1.000000 .
C(3) C 0.93071(7) -0.04518(7) 0.30604(5) 0.01055(12) Uani 1.000000 .
H(3a H 0.9828(11) -0.1489(13) 0.3081(8) 0.024(2) Uani 1.000000 .
C(4) C 1.01199(7) 0.04269(7) 0.22132(5) 0.01144(13) Uani 1.000000 .
C(5) C 1.14245(7) 0.03191(7) 0.04930(5) 0.01326(13) Uani 1.000000 .
H(5a H 1.2196(12) 0.1121(14) 0.0939(8) 0.034(3) Uani 1.000000 .
C(6) C 1.05045(7) 0.10604(7) -0.05034(5) 0.01221(12) Uani 1.000000 .
C(7) C 1.16625(8) -0.01533(10) 0.66851(6) 0.02105(16) Uani 1.000000 .
H(7a H 1.1883(14) 0.0459(15) 0.7476(10) 0.048(3) Uani 1.000000 .
H(7b H 1.1859(13) -0.1286(18) 0.6802(11) 0.048(3) Uani 1.000000 .
H(7c H 1.2469(14) 0.0255(18) 0.6065(9) 0.056(4) Uani 1.000000 .
C(8) C 1.24128(10) -0.08525(10) 0.00270(7) 0.02621(17) Uani 1.000000 .
H(8a H 1.3090(17) -0.1396(17) 0.0707(11) 0.061(4) Uani 1.000000 .
H(8b H 1.1686(16) -0.1640(16) -0.0413(12) 0.054(4) Uani 1.000000 .
H(8c H 1.3138(14) -0.0396(17) -0.0557(11) 0.054(4) Uani 1.000000 .
C(9) C 0.75551(7) -0.06558(7) 0.27432(6) 0.01262(12) Uani 1.000000 .
H(9a H 0.7428(11) -0.1238(13) 0.1966(10) 0.033(3) Uani 1.000000 .
H(9b H 0.7163(11) -0.1359(13) 0.3385(9) 0.027(2) Uani 1.000000 .
C(10 C 0.65791(7) 0.06570(7) 0.26453(5) 0.01296(12) Uani 1.000000 .
C(11 C 0.51863(8) 0.24132(8) 0.31577(6) 0.01802(14) Uani 1.000000 .
H(11 H 0.4590(15) 0.3224(14) 0.3659(10) 0.045(3) Uani 1.000000 .
C(12 C 0.59313(8) 0.13020(8) 0.16789(6) 0.01715(14) Uani 1.000000 .
H(12 H 0.6001(12) 0.1024(16) 0.0813(10) 0.045(3) Uani 1.000000 .
O(5) O 0.62488(6) 0.06598(6) 0.58425(4) 0.01679(10) Uani 1.000000 .
C(13 C 0.54326(9) 0.14872(9) 0.75862(6) 0.02119(15) Uani 1.000000 .
H(1d H 0.4736(14) 0.0506(15) 0.7633(9) 0.043(3) Uani 1.000000 .
H(1e H 0.6574(15) 0.1352(17) 0.8022(9) 0.051(4) Uani 1.000000 .
H(1f H 0.4838(14) 0.2360(16) 0.7994(9) 0.047(4) Uani 1.000000 .
C(14 C 0.55857(8) 0.18689(8) 0.63615(5) 0.01555(14) Uani 1.000000 .
H(14 H 0.4412(14) 0.2077(13) 0.5903(9) 0.038(3) Uani 1.000000 .
C(15 C 0.65699(10) 0.31955(9) 0.62613(8) 0.02716(17) Uani 1.000000 .
H(1g H 0.7698(18) 0.3010(17) 0.6722(13) 0.060(4) Uani 1.000000 .
H(1h H 0.6776(16) 0.3421(17) 0.5378(13) 0.061(4) Uani 1.000000 .
H(1i H 0.6066(18) 0.4134(16) 0.6624(14) 0.067(4) Uani 1.000000 .
O(6) O 0.68279(7) -0.11668(8) -0.03400(5) 0.01971(11) Uani 1.000000 .
H(5b H 0.6250(13) 0.0887(15) 0.5028(12) 0.038(3) Uani 1.000000 .
H(6a H 0.7653(17) -0.0495(16) -0.0464(10) 0.034(3) Uani 1.000000 .
H(6b H 0.7378(16) -0.1876(14) 0.0083(12) 0.029(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
H(1b N(1) H(1a 110.4(10) . . ?
H(1c N(1) H(1a 106.7(10) . . ?
H(1c N(1) H(1b 108.8(11) . . ?
C(1) N(1) H(1a 108.7(7) . . ?
C(1) N(1) H(1b 110.4(7) . . ?
C(1) N(1) H(1c 111.7(8) . . ?
C(2) N(2) H(2) 120.7(6) . . ?
C(3) N(2) H(2) 119.6(6) . . ?
C(3) N(2) C(2) 119.65(6) . . ?
C(4) N(3) H(3) 117.2(6) . . ?
C(5) N(3) H(3) 121.0(6) . . ?
C(5) N(3) C(4) 121.67(6) . . ?
C(11 N(4) C(10 105.75(5) . . ?
C(11 N(5) H(5) 128.0(6) . . ?
C(12 N(5) H(5) 124.7(6) . . ?
C(12 N(5) C(11 107.18(6) . . ?
H(1) C(1) N(1) 108.2(6) . . ?
C(2) C(1) N(1) 106.45(5) . . ?
C(2) C(1) H(1) 110.4(6) . . ?
C(7) C(1) N(1) 110.61(5) . . ?
C(7) C(1) H(1) 110.1(6) . . ?
C(7) C(1) C(2) 111.02(5) . . ?
N(2) C(2) O(1) 123.57(6) . . ?
C(1) C(2) O(1) 120.03(6) . . ?
C(1) C(2) N(2) 116.41(6) . . ?
H(3a C(3) N(2) 107.8(5) . . ?
C(4) C(3) N(2) 108.30(5) . . ?
C(4) C(3) H(3a 106.4(5) . . ?
C(9) C(3) N(2) 112.32(5) . . ?
C(9) C(3) H(3a 107.3(5) . . ?
C(9) C(3) C(4) 114.34(5) . . ?
N(3) C(4) O(2) 123.72(6) . . ?
C(3) C(4) O(2) 121.62(6) . . ?
C(3) C(4) N(3) 114.63(6) . . ?
H(5a C(5) N(3) 108.0(5) . . ?
C(6) C(5) N(3) 113.87(5) . . ?
C(6) C(5) H(5a 108.2(6) . . ?
C(8) C(5) N(3) 109.53(6) . . ?
C(8) C(5) H(5a 109.0(6) . . ?
C(8) C(5) C(6) 108.22(5) . . ?
O(4) C(6) O(3) 124.47(6) . . ?
C(5) C(6) O(3) 119.10(6) . . ?
C(5) C(6) O(4) 116.26(6) . . ?
H(7a C(7) C(1) 107.6(6) . . ?
H(7b C(7) C(1) 110.4(6) . . ?
H(7b C(7) H(7a 112.8(10) . . ?
H(7c C(7) C(1) 109.3(6) . . ?
H(7c C(7) H(7a 108.3(10) . . ?
H(7c C(7) H(7b 108.4(10) . . ?
H(8a C(8) C(5) 110.4(7) . . ?
H(8b C(8) C(5) 110.2(7) . . ?
H(8b C(8) H(8a 107.2(11) . . ?
H(8c C(8) C(5) 109.6(8) . . ?
H(8c C(8) H(8a 111.3(10) . . ?
H(8c C(8) H(8b 108.2(10) . . ?
H(9a C(9) C(3) 107.0(5) . . ?
H(9b C(9) C(3) 105.7(5) . . ?
H(9b C(9) H(9a 106.6(8) . . ?
C(10 C(9) C(3) 117.18(6) . . ?
C(10 C(9) H(9a 109.9(6) . . ?
C(10 C(9) H(9b 109.8(6) . . ?
C(9) C(10 N(4) 122.93(6) . . ?
C(12 C(10 N(4) 109.15(6) . . ?
C(12 C(10 C(9) 127.79(6) . . ?
N(5) C(11 N(4) 111.50(6) . . ?
H(11 C(11 N(4) 126.3(6) . . ?
H(11 C(11 N(5) 122.2(6) . . ?
C(10 C(12 N(5) 106.41(6) . . ?
H(12 C(12 N(5) 123.4(7) . . ?
H(12 C(12 C(10 130.1(7) . . ?
H(5b O(5) C(14 106.8(8) . . ?
H(1e C(13 H(1d 111.1(10) . . ?
H(1f C(13 H(1d 108.2(9) . . ?
H(1f C(13 H(1e 108.7(9) . . ?
C(14 C(13 H(1d 110.0(6) . . ?
C(14 C(13 H(1e 109.1(6) . . ?
C(14 C(13 H(1f 109.6(6) . . ?
C(13 C(14 O(5) 107.67(6) . . ?
H(14 C(14 O(5) 108.0(6) . . ?
H(14 C(14 C(13 110.4(6) . . ?
C(15 C(14 O(5) 111.01(6) . . ?
C(15 C(14 C(13 111.66(6) . . ?
C(15 C(14 H(14 108.1(7) . . ?
H(1g C(15 C(14 108.4(8) . . ?
H(1h C(15 C(14 112.0(8) . . ?
H(1h C(15 H(1g 106.9(10) . . ?
H(1i C(15 C(14 112.2(8) . . ?
H(1i C(15 H(1g 107.7(11) . . ?
H(1i C(15 H(1h 109.4(12) . . ?
H(6b O(6) H(6a 101.2(10) . . ?
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) C(2) 1.2440(9) . ?
O(2) C(4) 1.2406(9) . ?
O(3) C(6) 1.2636(9) . ?
O(4) C(6) 1.2629(8) . ?
N(1) H(1a 1.070(14) . ?
N(1) H(1b 1.023(16) . ?
N(1) H(1c 1.094(15) . ?
N(1) C(1) 1.5006(9) . ?
N(2) H(2) 1.008(14) . ?
N(2) C(2) 1.3431(8) . ?
N(2) C(3) 1.4628(8) . ?
N(3) H(3) 0.997(13) . ?
N(3) C(4) 1.3439(9) . ?
N(3) C(5) 1.4636(9) . ?
N(4) C(10 1.3942(9) . ?
N(4) C(11 1.3359(9) . ?
N(5) H(5) 1.038(14) . ?
N(5) C(11 1.3613(10) . ?
N(5) C(12 1.3848(10) . ?
C(1) H(1) 1.103(12) . ?
C(1) C(2) 1.5358(9) . ?
C(1) C(7) 1.5310(10) . ?
C(3) H(3a 1.077(12) . ?
C(3) C(4) 1.5362(9) . ?
C(3) C(9) 1.5541(9) . ?
C(5) H(5a 1.115(13) . ?
C(5) C(6) 1.5420(9) . ?
C(5) C(8) 1.5391(10) . ?
C(7) H(7a 1.111(12) . ?
C(7) H(7b 1.087(16) . ?
C(7) H(7c 1.139(12) . ?
C(8) H(8a 1.089(13) . ?
C(8) H(8b 1.081(16) . ?
C(8) H(8c 1.078(13) . ?
C(9) H(9a 1.077(13) . ?
C(9) H(9b 1.095(11) . ?
C(9) C(10 1.5006(9) . ?
C(10 C(12 1.3808(10) . ?
C(11 H(11 1.129(13) . ?
C(12 H(12 1.078(12) . ?
O(5) C(14 1.4455(9) . ?
O(5) H(5b 1.000(14) . ?
C(13 H(1d 1.111(14) . ?
C(13 H(1e 1.088(13) . ?
C(13 H(1f 1.111(13) . ?
C(13 C(14 1.5299(10) . ?
C(14 H(14 1.134(12) . ?
C(14 C(15 1.5284(11) . ?
C(15 H(1g 1.097(17) . ?
C(15 H(1h 1.112(15) . ?
C(15 H(1i 1.097(15) . ?
O(6) H(6a 0.981(16) . ?
O(6) H(6b 0.942(16) . ?
