# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_P
_database_code_depnum_ccdc_archive 'CCDC 1968023'
loop_
_audit_author_name
_audit_author_address
'Ruifang Guan'
;University of Jinan
China
;
_audit_update_record             
;
2020-03-07 deposited with the CCDC.	2020-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        Propanedihydrazide
_chemical_name_common            'Malonic dihydrazide'
_chemical_melting_point          152-154\^A\%C
_chemical_formula_moiety         'C3 H10 N4 O3'
_chemical_formula_sum            'C3 H10 N4 O3'
_chemical_formula_weight         150.15

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   9.1606(6)
_cell_length_b                   9.7305(6)
_cell_length_c                   7.8691(6)
_cell_angle_alpha                90
_cell_angle_beta                 102.839(7)
_cell_angle_gamma                90
_cell_volume                     683.89(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2525
_cell_measurement_theta_min      3.4010
_cell_measurement_theta_max      29.5670

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.987
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5659
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.381
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1388
_reflns_number_gt                1162
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0309P)²+0.2356P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.017(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1388
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0192(5) 0.0216(5) 0.0219(5) 0.0003(4) 0.0060(4) 0.0035(4)
O2 0.0214(5) 0.0193(5) 0.0219(5) -0.0008(4) 0.0071(4) 0.0021(4)
N1 0.0197(6) 0.0211(6) 0.0274(7) -0.0039(5) 0.0081(5) -0.0040(4)
N2 0.0191(6) 0.0158(6) 0.0258(7) -0.0043(5) 0.0082(5) -0.0018(4)
N3 0.0169(5) 0.0203(6) 0.0195(6) 0.0035(5) 0.0045(4) 0.0006(4)
N4 0.0186(6) 0.0240(6) 0.0197(6) 0.0006(5) 0.0061(5) -0.0015(5)
C1 0.0179(6) 0.0179(6) 0.0120(7) 0.0030(5) 0.0023(5) 0.0007(5)
C2 0.0198(6) 0.0241(7) 0.0173(7) -0.0023(5) 0.0048(5) -0.0039(5)
C3 0.0170(6) 0.0146(6) 0.0185(7) -0.0043(5) 0.0035(5) -0.0027(5)
O1W 0.0205(5) 0.0258(6) 0.0435(7) -0.0070(5) 0.0121(5) -0.0019(4)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) .

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.042

_shelx_res_file                  
;

    P.res created by SHELXL-2014/7


TITL 180716d_a.res in P2(1)/c
REM Old TITL 180716D in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.130, Rweak 0.003, Alpha 0.013, Orientation as input
REM Formula found by SHELXT: N4 N3 N2
CELL 0.71073 9.1606 9.7305 7.8691 90 102.839 90
ZERR 4 0.0006 0.0006 0.0006 0 0.007 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 12 40 16 12
HTAB
SIZE 0.1 0.11 0.12
L.S. 4
PLAN  5
BOND $H
LIST 6
fmap 2
EQIV $1 x, -y+3/2, z-1/2
HTAB N1 O1_$1
EQIV $2 -x+1, -y+2, -z+1
HTAB N1 O2_$2
EQIV $3 -x+1, y+1/2, -z+3/2
HTAB N1 O1_$3
EQIV $4 -x+1, -y+1, -z+1
HTAB N2 O1_$4
HTAB N3 O1W_$1
EQIV $5 x, -y+3/2, z+1/2
HTAB N4 O2_$5
EQIV $6 -x, y-1/2, -z+3/2
HTAB N4 O1W_$6
EQIV $7 x-1, -y+3/2, z+1/2
HTAB O1W N1_$7
HTAB O1W N4
acta
SHEL 999 0.8
OMIT -1 1 2
REM <olex2.extras>
REM <HklSrc "%.\\P.hkl">
REM </olex2.extras>

WGHT    0.030900    0.235600
EXTI    0.016724
FVAR       0.97746
O1    4    0.352308    0.489187    0.690826    11.00000    0.01921    0.02157 =
         0.02195    0.00034    0.00598    0.00350
O2    4    0.338993    0.851041    0.546900    11.00000    0.02138    0.01933 =
         0.02191   -0.00085    0.00715    0.00211
N1    3    0.617754    0.845520    0.460815    11.00000    0.01972    0.02105 =
         0.02741   -0.00393    0.00810   -0.00402
AFIX   7
H1A   2    0.580484    0.915230    0.398464    11.00000   -1.20000
AFIX   0
H1B   2    0.633439    0.873209    0.572430    11.00000    0.02961
N2    3    0.512161    0.737529    0.436152    11.00000    0.01913    0.01578 =
         0.02581   -0.00430    0.00824   -0.00178
AFIX  43
H2    2    0.534625    0.661241    0.393024    11.00000   -1.20000
AFIX   0
N3    3    0.122776    0.586138    0.638523    11.00000    0.01690    0.02032 =
         0.01947    0.00346    0.00453    0.00061
AFIX  43
H3    2    0.060069    0.639231    0.571627    11.00000   -1.20000
AFIX   0
N4    3    0.083300    0.529321    0.788182    11.00000    0.01863    0.02396 =
         0.01973    0.00064    0.00609   -0.00151
AFIX   7
H4A   2    0.154251    0.544141    0.878872    11.00000   -1.20000
AFIX   0
H4B   2    0.080552    0.436371    0.769244    11.00000    0.03139
C1    1    0.379164    0.749068    0.476999    11.00000    0.01790    0.01795 =
         0.01203    0.00302    0.00234    0.00068
C2    1    0.277437    0.624426    0.432278    11.00000    0.01983    0.02411 =
         0.01732   -0.00228    0.00481   -0.00392
AFIX  23
H2A   2    0.181924    0.652256    0.360053    11.00000   -1.20000
H2B   2    0.322757    0.558208    0.367555    11.00000   -1.20000
AFIX   0
C3    1    0.253777    0.559969    0.598172    11.00000    0.01698    0.01458 =
         0.01845   -0.00427    0.00351   -0.00274

O1W   4   -0.092167    0.741689    0.906050    11.00000    0.02054    0.02577 =
         0.04353   -0.00699    0.01211   -0.00189
H1WA  2   -0.181193    0.717870    0.915606    11.00000    0.04674
H1WB  2   -0.053722    0.666042    0.872826    11.00000    0.05630
HKLF 4

REM  180716d_a.res in P2(1)/c
REM R1 =  0.0330 for    1162 Fo > 4sig(Fo)  and  0.0403 for all    1388 data
REM    110 parameters refined using      0 restraints

END

WGHT      0.0309      0.2356

REM Instructions for potential hydrogen bonds
HTAB N1 O1_$1
HTAB N1 O2_$2
HTAB N1 O1_$3
HTAB N2 O1_$4
HTAB N3 O1W_$1
HTAB N4 O2_$5
HTAB N4 O1W_$6
HTAB O1W N1_$7
HTAB O1W N4

REM Highest difference peak  0.268,  deepest hole -0.180,  1-sigma level  0.042
Q1    1   0.3354  0.6808  0.4684  11.00000  0.05    0.27
Q2    1   0.7091  0.8319  0.4393  11.00000  0.05    0.18
Q3    1  -0.0138  0.5342  0.8038  11.00000  0.05    0.18
Q4    1   0.2632  0.6096  0.5193  11.00000  0.05    0.18
Q5    1   0.4286  0.7555  0.4178  11.00000  0.05    0.15
;
_shelx_res_checksum              58140
