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_7061964
_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         'C4 H12 N2 O2, C2 O4, 0.901(H2 O)'
_chemical_formula_sum            'C6 H13.8 N2 O6.9'
_chemical_formula_weight         224.40
_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             2022-05-24
_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                 97.0180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.54180(10)
_cell_length_b                   9.76040(10)
_cell_length_c                   10.15310(10)
_cell_measurement_reflns_used    11061
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      77.4690
_cell_measurement_theta_min      4.3940
_cell_volume                     938.492(17)
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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     41.00 120.00   0.50    0.25    --  107.75-137.00 143.00  158
  2  \w     36.00 111.00   0.50    0.25    --  107.75-125.00  60.00  150
  3  \w     38.00 116.00   0.50    0.25    --  107.75-132.00 -39.00  156
  4  \w     37.00  79.00   0.50    0.25    --  107.75 -95.00-150.00   84
  5  \w     36.00 111.00   0.50    0.25    --  107.75-125.00-120.00  150
  6  \w     71.00 106.00   0.50    0.25    --  107.75-125.00 -90.00   70
  7  \w     36.00 106.00   0.50    0.25    --  107.75 -96.00 -22.64  140
  8  \w     36.00 105.00   0.50    0.25    --  107.75 -95.00 -60.00  138
  9  \w     38.00  99.00   0.50    0.15    --   48.70-132.00 -39.00  122
 10  \w     66.00  98.00   0.50    0.25    --  107.75 -95.00 120.00   64
 11  \w     39.00  66.00   0.50    0.25    --  107.75 -61.00  30.00   54
 12  \w     36.00 105.00   0.50    0.25    --  107.75 -77.00   0.00  138
 13  \w     36.00  71.00   0.50    0.25    --  107.75 -61.00 -30.00   70
 14  \w     36.00 105.00   0.50    0.25    --  107.75 -77.00 -90.00  138
 15  \w     36.00  98.00   0.50    0.25    --  107.75 -77.00-120.00  124
 16  \w     36.00  71.00   0.50    0.25    --  107.75 -61.00 -60.00   70
 17  \w     36.00  71.00   0.50    0.25    --  107.75 -61.00   0.00   70
 18  \w     36.00  71.00   0.50    0.25    --  107.75 -61.00  90.00   70
 19  \w     97.00 178.00   0.50    0.25    --  107.75  30.00 -30.00  162
 20  \w    127.00 153.00   0.50    0.25    --  107.75  45.00-180.00   52
 21  \w     97.00 178.00   0.50    0.25    --  107.75  45.00-150.00  162
 22  \w    126.00 154.00   0.50    0.25    --  107.75  45.00   0.00   56
 23  \w    108.00 173.00   0.50    0.25    --  107.75  30.00  60.00  130
 24  \w    107.00 151.00   0.50    0.25    --  107.75  61.00 120.00   88
 25  \w     91.00 178.00   0.50    0.25    --  107.75 132.00  28.00  174
 26  \w    130.00 156.00   0.50    0.25    --  107.75 125.00 -30.00   52
 27  \w     96.00 130.00   0.50    0.25    --  107.75 125.00-120.00   68
 28  \w    135.00 161.00   0.50    0.25    --  107.75 125.00-120.00   52
 29  \w    -26.00  26.00   0.50    0.15    --  -48.70  19.00-180.00  104
 30  \w    -91.00 -17.00   0.50    0.15    --  -48.70 132.00  28.00  148
 31  \w    -51.00 -14.00   0.50    0.25    --  -86.25  45.00-120.00   74
 32  \w   -120.00 -69.00   0.50    0.15    --  -48.70-132.00 -39.00  102
 33  \w   -158.00 -69.00   0.50    0.25    --  -86.25-132.00 -39.00  178
 34  \w   -120.00 -66.00   0.50    0.15    --  -48.70-137.00 143.00  108
 35  \w   -120.00 -27.00   0.50    0.15    --  -48.70 -77.00  60.00  186
;
_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      -0.0160460000
_diffrn_orient_matrix_UB_12      -0.1570529000
_diffrn_orient_matrix_UB_13      -0.0018724000
_diffrn_orient_matrix_UB_21      -0.1594514000
_diffrn_orient_matrix_UB_22      0.0153643000
_diffrn_orient_matrix_UB_23      0.0076703000
_diffrn_orient_matrix_UB_31      -0.0277622000
_diffrn_orient_matrix_UB_32      0.0027398000
_diffrn_orient_matrix_UB_33      -0.1527198000
_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  0.0173
_diffrn_reflns_av_unetI/netI     0.0095
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12301
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.832
_diffrn_reflns_theta_min         6.009
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.275
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80813
_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    1.588
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_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         0.344
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0475P)^2^+0.4398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0921
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1967
_reflns_number_total             1990
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj03012h2.cif
_cod_data_source_block           lvk520
_cod_depositor_comments
'Adding full bibliography for 7061962--7061964.cif.'
_cod_original_formula_sum        'C6 H13.80 N2 O6.90'
_cod_database_code               7061964
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_chemical_oxdiff_usercomment     LVK520
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Others
 Sof(O7)=Sof(H7A)=Sof(H7B)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C1(H1B,H1C), C2(H2B,H2C), C3(H3A,H3B), C4(H4A,H4B)
;
_shelx_res_checksum              95057
_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 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.740