#------------------------------------------------------------------------------
#$Date: 2020-05-05 15:40:48 +0300 (Tue, 05 May 2020) $
#$Revision: 251548 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/62/7126208.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7126208
loop_
_publ_author_name
'Guan, Ruifang'
'Dong, Baoli'
'Xu, Cui'
'Zhang, Hao'
'Cao, Duxia'
'Lin, Weiying'
_publ_section_title
;
 A strategy to construct fluorescent non-aromatic small-molecules:
 hydrogen bonds contributing to the unexpected fluorescence.
;
_journal_issue                   32
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4424
_journal_page_last               4427
_journal_paper_doi               10.1039/c9cc09906a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C3 H10 N4 O3'
_chemical_formula_sum            'C3 H10 N4 O3'
_chemical_formula_weight         150.15
_chemical_melting_point          152-154\^A\%C
_chemical_name_common            'Malonic dihydrazide'
_chemical_name_systematic        Propanedihydrazide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2020-03-07 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.839(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.1606(6)
_cell_length_b                   9.7305(6)
_cell_length_c                   7.8691(6)
_cell_measurement_reflns_used    2525
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5670
_cell_measurement_theta_min      3.4010
_cell_volume                     683.89(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5659
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         3.381
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1388
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0330
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0309P)²+0.2356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1162
_reflns_number_total             1388
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc09906a2.cif
_cod_data_source_block           P
_cod_depositor_comments          'Adding full bibliography for 7126208.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7126208
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.985
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.35231(10) 0.48919(10) 0.69083(13) 0.0207(3) Uani 1 1 d . . . . .
O2 O 0.33899(10) 0.85104(10) 0.54690(12) 0.0205(3) Uani 1 1 d . . . . .
N1 N 0.61775(12) 0.84552(12) 0.46081(18) 0.0223(3) Uani 1 1 d . . . . .
H1A H 0.5805 0.9152 0.3985 0.027 Uiso 1 1 d R U . . .
H1B H 0.6334(18) 0.8732(18) 0.572(3) 0.030(5) Uiso 1 1 d . . . . .
N2 N 0.51216(12) 0.73753(11) 0.43615(16) 0.0197(3) Uani 1 1 d . . . . .
H2 H 0.5346 0.6612 0.3930 0.024 Uiso 1 1 calc R U . . .
N3 N 0.12278(12) 0.58614(11) 0.63852(15) 0.0188(3) Uani 1 1 d . . . . .
H3 H 0.0601 0.6392 0.5716 0.023 Uiso 1 1 calc R U . . .
N4 N 0.08330(12) 0.52932(13) 0.78818(16) 0.0205(3) Uani 1 1 d . . . . .
H4A H 0.1543 0.5441 0.8789 0.025 Uiso 1 1 d R U . . .
H4B H 0.0806(18) 0.4364(19) 0.769(2) 0.031(5) Uiso 1 1 d . . . . .
C1 C 0.37916(14) 0.74907(13) 0.47700(17) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.27744(15) 0.62443(14) 0.43228(18) 0.0203(3) Uani 1 1 d . . . . .
H2A H 0.1819 0.6523 0.3601 0.024 Uiso 1 1 calc R U . . .
H2B H 0.3228 0.5582 0.3676 0.024 Uiso 1 1 calc R U . . .
C3 C 0.25378(14) 0.55997(13) 0.59817(17) 0.0167(3) Uani 1 1 d . . . . .
O1W O -0.09217(12) 0.74169(11) 0.90605(15) 0.0292(3) Uani 1 1 d . . . . .
H1WA H -0.181(2) 0.718(2) 0.916(3) 0.047(6) Uiso 1 1 d . . . . .
H1WB H -0.054(2) 0.666(2) 0.873(3) 0.056(6) Uiso 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
N2 N1 H1A 109.6 . . ?
N2 N1 H1B 108.2(11) . . ?
H1A N1 H1B 106.1 . . ?
C1 N2 N1 122.65(11) . . ?
C1 N2 H2 118.7 . . ?
N1 N2 H2 118.7 . . ?
C3 N3 N4 122.18(11) . . ?
C3 N3 H3 118.9 . . ?
N4 N3 H3 118.9 . . ?
N3 N4 H4A 109.7 . . ?
N3 N4 H4B 104.6(11) . . ?
H4A N4 H4B 106.7 . . ?
O2 C1 N2 123.82(12) . . ?
O2 C1 C2 121.17(11) . . ?
N2 C1 C2 115.01(11) . . ?
C3 C2 C1 109.26(11) . . ?
C3 C2 H2A 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C3 C2 H2B 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
O1 C3 N3 122.97(12) . . ?
O1 C3 C2 121.08(11) . . ?
N3 C3 C2 115.95(11) . . ?
H1WA O1W H1WB 104(2) . . ?
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
O1 C3 1.2362(16) . ?
O2 C1 1.2298(16) . ?
N1 N2 1.4121(16) . ?
N1 H1A 0.8620 . ?
N1 H1B 0.899(19) . ?
N2 C1 1.3320(17) . ?
N2 H2 0.8600 . ?
N3 C3 1.3323(17) . ?
N3 N4 1.4187(16) . ?
N3 H3 0.8600 . ?
N4 H4A 0.8639 . ?
N4 H4B 0.916(19) . ?
C1 C2 1.5223(18) . ?
C2 C3 1.5067(19) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O1W H1WA 0.87(2) . ?
O1W H1WB 0.88(2) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.86 2.53 3.2738(16) 145.5 4_575
N1 H1A O2 0.86 2.40 2.9815(15) 125.2 3_676
N1 H1B O1 0.899(19) 2.16(2) 3.0348(17) 165.1(16) 2_656
N2 H2 O1 0.86 1.99 2.8210(15) 162.6 3_666
N3 H3 O1W 0.86 2.04 2.9033(16) 177.5 4_575
N4 H4A O2 0.86 2.16 2.9778(15) 158.2 4_576
N4 H4B O1W 0.916(19) 2.360(19) 3.1986(17) 152.2(15) 2_546
O1W H1WA N1 0.87(2) 2.05(2) 2.9114(16) 174.6(19) 4_476
O1W H1WB N4 0.88(2) 2.04(2) 2.8943(17) 163(2) .
