Weak hydrogen and dihydrogen bonds instead of strong N–H⋯O bonds of a tricyclic [1,2,4,5]-tetrazine derivative. Single-crystal X-ray diffraction, theoretical calculations and Hirshfeld surface analysis
Owczarek, Magdalena; Majerz, Irena; Jakubas, Ryszard; CrystEngComm 16 (2014) 7638–; doi:10.1039/C4CE00571F

data_7216388
_publ_section_title
;
 Weak hydrogen and dihydrogen bonds instead of strong N--H&#x22EF;O bonds
 of a tricyclic [1,2,4,5]-tetrazine derivative. Single-crystal X-ray
 diffraction, theoretical calculations and Hirshfeld surface analysis
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              7638
_journal_paper_doi               10.1039/C4CE00571F
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H16 N4 O2, H2 O'
_chemical_formula_sum            'C8 H18 N4 O3'
_chemical_formula_weight         218.26
_space_group_IT_number           15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.56(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.088(5)
_cell_length_b                   4.672(3)
_cell_length_c                   12.691(5)
_cell_measurement_temperature    100(2)
_cell_volume                     1021.0(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8486
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         36.70
_diffrn_reflns_theta_min         3.32
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     69
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0372
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.1903P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1083
_refine_ls_wR_factor_ref         0.1116
_reflns_number_gt                1970
_reflns_number_total             2375
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00571f2.cif
_cod_data_source_block           owczq
_cod_depositor_comments
'Adding full bibliography for 7216388--7216389.cif.'
_cod_original_cell_volume        1021.0(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7216388