Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of supramolecular hydrogen-bonded 2D networks
Lesnikov, Vladislav K.; Nelyubina, Yulia V.; Sukhorukov, Alexey Yu.; New Journal of Chemistry 46 (2022) 20386–20394; doi:10.1039/D2NJ03012H

data_7061963
_publ_section_title
;
 Piperazine-1,4-diol (PipzDiol): synthesis, stereodynamics and assembly of
 supramolecular hydrogen-bonded 2D networks
;
_journal_issue                   42
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              20386
_journal_page_last               20394
_journal_paper_doi               10.1039/D2NJ03012H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C7 H7 N O2, 0.5(C4 H10 N2 O2)'
_chemical_formula_sum            'C9 H12 N2 O3'
_chemical_formula_weight         196.21
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-05-26
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6429)
;
_audit_update_record
;
2022-06-01 deposited with the CCDC.	2022-10-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 116.019(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.63990(10)
_cell_length_b                   8.49780(10)
_cell_length_c                   11.93370(10)
_cell_measurement_reflns_used    11168
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.5780
_cell_measurement_theta_min      4.6420
_cell_volume                     969.64(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.54a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00 107.00   0.50    0.15    --  107.75-112.00-133.73  142
  2  \w     49.00  75.00   0.50    0.15    --  107.75-125.00-120.00   52
  3  \w     68.00 109.00   0.50    0.15    --  107.75-125.00 -60.00   82
  4  \w     36.00 105.00   0.50    0.15    --  107.75 -95.00   0.00  138
  5  \w     40.00  66.00   0.50    0.15    --  107.75 -95.00 -60.00   52
  6  \w     36.00 134.00   0.50    0.15    --  107.75 -87.00-108.98  196
  7  \w     37.00  62.00   0.50    0.15    --  107.75 -55.00-120.35   50
  8  \w     40.00  66.00   0.50    0.15    --  107.75 -77.00 -90.00   52
  9  \w     80.00 105.00   0.50    0.15    --  107.75 -77.00 -90.00   50
 10  \w     36.00 105.00   0.50    0.15    --  107.75 -77.00 -30.00  138
 11  \w     72.00 108.00   0.50    0.15    --  107.75 -78.00  75.36   72
 12  \w     73.00  99.00   0.50    0.15    --  107.75 -77.00 150.00   52
 13  \w     71.00  96.00   0.50    0.15    --  107.75 -77.00 120.00   50
 14  \w     36.00  71.00   0.50    0.15    --  107.75 -61.00 120.00   70
 15  \w     37.00  67.00   0.50    0.15    --  107.75 -77.00 120.00   60
 16  \w     36.00  71.00   0.50    0.15    --  107.75 -61.00 150.00   70
 17  \w     36.00 105.00   0.50    0.15    --  107.75 -77.00  90.00  138
 18  \w     36.00  89.00   0.50    0.15    --  107.75 -71.00  65.00  106
 19  \w     37.00  63.00   0.50    0.15    --  107.75 -61.00  90.00   52
 20  \w     45.00  71.00   0.50    0.15    --  107.75 -61.00  60.00   52
 21  \w     37.00  62.00   0.50    0.15    --  107.75 -77.00 -60.00   50
 22  \w     99.00 162.00   0.50    0.15    --  107.75  30.00 120.00  126
 23  \w     86.00 156.00   0.50    0.15    --  107.75  77.00  30.00  140
 24  \w    109.00 173.00   0.50    0.15    --  107.75  45.00   0.00  128
 25  \w    134.00 176.00   0.50    0.15    --  107.75  30.00 150.00   84
 26  \w     99.00 124.00   0.50    0.15    --  107.75  61.00 -60.00   50
 27  \w     97.00 178.00   0.50    0.15    --  107.75  45.00 -90.00  162
 28  \w     30.00 120.00   0.50    0.05    --   48.70  71.00-163.00  180
 29  \w     89.00 178.00   0.50    0.15    --  107.75  71.00-163.00  178
 30  \w     97.00 178.00   0.50    0.15    --  107.75  30.00-180.00  162
 31  \w     96.00 134.00   0.50    0.15    --  107.75 125.00-150.00   76
 32  \w    -68.00  24.00   0.50    0.05    --  -48.70  71.00-163.00  184
 33  \w    -89.00 -14.00   0.50    0.15    --  -86.25  71.00-163.00  150
 34  \w   -120.00 -73.00   0.50    0.05    --  -48.70-125.00-150.00   94
 35  \w   -120.00 -29.00   0.50    0.05    --  -48.70 -71.00  65.00  182
 36  \w    -22.00  68.00   0.50    0.05    --   48.70 -71.00  65.00  180
 37  \w    -25.00  26.00   0.50    0.05    --   48.70 -19.00 -90.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1369702000
_diffrn_orient_matrix_UB_12      0.0954746000
_diffrn_orient_matrix_UB_13      0.0554694000
_diffrn_orient_matrix_UB_21      0.0616757000
_diffrn_orient_matrix_UB_22      -0.1084777000
_diffrn_orient_matrix_UB_23      -0.0667300000
_diffrn_orient_matrix_UB_31      -0.0582605000
_diffrn_orient_matrix_UB_32      0.1094591000
_diffrn_orient_matrix_UB_33      -0.1144853000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12736
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.829
_diffrn_reflns_theta_min         4.654
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.54a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: MeOH, H2O'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0081(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0427
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0674P)^2^+0.3667P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1184
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2007
_reflns_number_total             2067
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03012h2.cif
_cod_data_source_block           lvk519
_cod_depositor_comments
'Adding full bibliography for 7061962--7061964.cif.'
_cod_database_code               7061963
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     LVK519
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8)
;
_shelx_res_checksum              58460
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.910
_oxdiff_exptl_absorpt_empirical_full_min 0.405