# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_I
_audit_block_doi                 10.5517/ccdc.csd.cc24r558
_database_code_depnum_ccdc_archive 'CCDC 1988469'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d0ce00359j 2020
loop_
_audit_author_name
_audit_author_address
'Zhengfeng Zhang'
; Henan Normal University
China
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        
;
2-cyano-N'-[(1E)-phenylmethylidene]acetohydrazide
;
_chemical_name_common            
;
benzaldehyde (cyanoacetyl)hydrazone
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H9 N3 O'
_chemical_formula_sum            'C10 H9 N3 O'
_chemical_formula_weight         187.20

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                   12.200(5)
_cell_length_b                   9.143(4)
_cell_length_c                   8.797(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.020(8)
_cell_angle_gamma                90
_cell_volume                     959.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    940
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      22.78

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_F_000             392.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4032
_diffrn_reflns_av_unetI/netI     0.0395
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.707
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_full        25.039
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1698
_reflns_number_gt                1020
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0538P)²] 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-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0051(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1698
_refine_ls_number_parameters     132
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0856
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
N2 N 0.60660(13) 0.24310(16) 0.09739(18) 0.0495(5) Uani 1 1 d . . . . .
N1 N 0.53301(14) 0.16641(17) 0.16963(19) 0.0503(5) Uani 1 1 d . . . . .
N3 N 0.2356(2) 0.2798(2) 0.4159(3) 0.0962(8) Uani 1 1 d . . . . .
O1 O 0.44413(11) 0.37180(12) 0.22468(17) 0.0611(5) Uani 1 1 d . . . . .
C4 C 0.68141(16) 0.1641(2) 0.0552(2) 0.0510(5) Uani 1 1 d . . . . .
H4 H 0.680673 0.063715 0.072039 0.061 Uiso 1 1 calc R U . . .
C5 C 0.76756(17) 0.22490(19) -0.0180(2) 0.0479(5) Uani 1 1 d . . . . .
C6 C 0.77614(17) 0.3746(2) -0.0442(2) 0.0555(6) Uani 1 1 d . . . . .
H6 H 0.723345 0.438467 -0.018893 0.067 Uiso 1 1 calc R U . . .
C7 C 0.86218(19) 0.4282(2) -0.1070(2) 0.0675(7) Uani 1 1 d . . . . .
H7 H 0.867192 0.528246 -0.123561 0.081 Uiso 1 1 calc R U . . .
C8 C 0.9412(2) 0.3353(3) -0.1460(3) 0.0709(7) Uani 1 1 d . . . . .
H8 H 0.999487 0.372317 -0.187936 0.085 Uiso 1 1 calc R U . . .
C9 C 0.9328(2) 0.1872(3) -0.1219(3) 0.0715(7) Uani 1 1 d . . . . .
H9 H 0.985567 0.123841 -0.148136 0.086 Uiso 1 1 calc R U . . .
C10 C 0.84681(18) 0.1324(2) -0.0593(2) 0.0601(6) Uani 1 1 d . . . . .
H10 H 0.841749 0.032117 -0.044395 0.072 Uiso 1 1 calc R U . . .
C1 C 0.45758(17) 0.23891(18) 0.2312(2) 0.0465(5) Uani 1 1 d . . . . .
C2 C 0.38820(17) 0.13962(19) 0.3120(3) 0.0567(6) Uani 1 1 d . . . . .
H2B H 0.353781 0.064274 0.240031 0.068 Uiso 1 1 calc R U . . .
H2A H 0.437066 0.091895 0.398945 0.068 Uiso 1 1 calc R U . . .
C3 C 0.3018(2) 0.2180(2) 0.3679(3) 0.0597(6) Uani 1 1 d . . . . .
H1 H 0.5437(15) 0.069(2) 0.188(2) 0.067(6) Uiso 1 1 d . . . . .


_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
N2 C4 1.278(2) . ?
N2 N1 1.393(2) . ?
N1 C1 1.337(2) . ?
N1 H1 0.91(2) . ?
N3 C3 1.136(3) . ?
O1 C1 1.2259(19) . ?
C4 C5 1.453(3) . ?
C4 H4 0.9300 . ?
C5 C10 1.389(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C1 C2 1.515(3) . ?
C2 C3 1.443(3) . ?
C2 H2B 0.9700 . ?
C2 H2A 0.9700 . ?

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
C4 N2 N1 114.53(15) . . ?
C1 N1 N2 119.93(16) . . ?
C1 N1 H1 119.7(12) . . ?
N2 N1 H1 119.6(12) . . ?
N2 C4 C5 122.60(18) . . ?
N2 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C10 C5 C6 118.3(2) . . ?
C10 C5 C4 119.35(18) . . ?
C6 C5 C4 122.31(18) . . ?
C7 C6 C5 120.39(19) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 119.2(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C5 C10 H10 119.6 . . ?
O1 C1 N1 124.68(18) . . ?
O1 C1 C2 122.25(18) . . ?
N1 C1 C2 113.07(15) . . ?
C3 C2 C1 112.39(15) . . ?
C3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
H2B C2 H2A 107.9 . . ?
N3 C3 C2 178.1(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N2 N1 C1 174.02(18) . . . . ?
N1 N2 C4 C5 -178.21(17) . . . . ?
N2 C4 C5 C10 179.33(19) . . . . ?
N2 C4 C5 C6 1.5(3) . . . . ?
C10 C5 C6 C7 -1.0(3) . . . . ?
C4 C5 C6 C7 176.88(19) . . . . ?
C5 C6 C7 C8 0.2(3) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C6 C5 C10 C9 1.1(3) . . . . ?
C4 C5 C10 C9 -176.81(19) . . . . ?
N2 N1 C1 O1 2.9(3) . . . . ?
N2 N1 C1 C2 -177.16(17) . . . . ?
O1 C1 C2 C3 4.2(3) . . . . ?
N1 C1 C2 C3 -175.75(19) . . . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.91(2) 1.95(2) 2.844(2) 166.2(16) 2_645 yes
N1 H1 O1 0.91(2) 1.95(2) 2.844(2) 166.2(16) 2_645 yes

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.030

####################################################################### 
# 
# 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_II
_audit_block_doi                 10.5517/ccdc.csd.cc1klfvf
_database_code_depnum_ccdc_archive 'CCDC 1447695'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/d0ce00359j 2020
loop_
_audit_author_name
_audit_author_address
'Zhengfeng Zhang'
; Henan Normal University
China
;
_audit_update_record             
;
2020-04-23 deposited with the CCDC.	2020-05-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.6847(17)
_cell_length_b                   9.1876(18)
_cell_length_c                   27.083(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2161.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1627
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      24.36

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.972
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10907
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.504
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1911
_reflns_number_gt                1231
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0561P)²+0.6848P] 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-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0049(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1911
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1278
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N3 N 0.7128(2) -0.5072(3) -0.11633(8) 0.0769(8) Uani 1 1 d . . . . .
C3 C 0.7728(2) -0.4351(3) -0.08822(8) 0.0528(6) Uani 1 1 d . . . . .
O2 O 0.57665(19) 0.3283(2) 0.23364(6) 0.0701(6) Uani 1 1 d . . . . .
O1 O 0.61814(16) -0.2514(2) -0.02575(6) 0.0650(6) Uani 1 1 d . . . . .
N2 N 0.74304(19) -0.0779(2) 0.04661(7) 0.0505(5) Uani 1 1 d . . . . .
N1 N 0.8205(2) -0.1669(2) 0.01366(7) 0.0519(6) Uani 1 1 d . . . . .
C8 C 0.6435(2) 0.2476(3) 0.19717(8) 0.0519(6) Uani 1 1 d . . . . .
C9 C 0.7907(3) 0.2132(3) 0.19626(9) 0.0582(7) Uani 1 1 d . . . . .
H9 H 0.856391 0.244417 0.221235 0.070 Uiso 1 1 calc R U . . .
C10 C 0.8463(2) 0.1297(3) 0.15755(8) 0.0564(7) Uani 1 1 d . . . . .
H10 H 0.950700 0.107218 0.157598 0.068 Uiso 1 1 calc R U . . .
C5 C 0.7594(2) 0.0777(3) 0.11923(8) 0.0465(6) Uani 1 1 d . . . . .
C6 C 0.6119(2) 0.1162(3) 0.12053(8) 0.0510(6) Uani 1 1 d . . . . .
H6 H 0.546158 0.086392 0.095390 0.061 Uiso 1 1 calc R U . . .
C7 C 0.5555(2) 0.1994(3) 0.15856(9) 0.0551(7) Uani 1 1 d . . . . .
H7 H 0.451705 0.224395 0.158063 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8214(2) -0.0159(3) 0.08075(8) 0.0500(6) Uani 1 1 d . . . . .
H4 H 0.927127 -0.032180 0.080945 0.060 Uiso 1 1 calc R U . . .
C11 C 0.6602(3) 0.3711(4) 0.27576(9) 0.0841(10) Uani 1 1 d . . . . .
H11A H 0.696634 0.286260 0.292822 0.126 Uiso 1 1 calc R U . . .
H11B H 0.594582 0.426394 0.297259 0.126 Uiso 1 1 calc R U . . .
H11C H 0.746290 0.429854 0.265913 0.126 Uiso 1 1 calc R U . . .
C1 C 0.7502(2) -0.2504(3) -0.01999(8) 0.0475(6) Uani 1 1 d . . . . .
C2 C 0.8512(3) -0.3449(3) -0.05218(9) 0.0591(7) Uani 1 1 d . . . . .
H2A H 0.922790 -0.282236 -0.069618 0.071 Uiso 1 1 calc R U . . .
H2B H 0.911397 -0.407851 -0.030871 0.071 Uiso 1 1 calc R U . . .
H1 H 0.919(3) -0.181(3) 0.0200(9) 0.082(9) Uiso 1 1 d . . . . .


_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
N3 C3 1.136(3) . ?
C3 C2 1.450(3) . ?
O2 C8 1.365(3) . ?
O2 C11 1.408(3) . ?
O1 C1 1.158(2) . ?
N2 C4 1.282(3) . ?
N2 N1 1.385(3) . ?
N1 C1 1.339(3) . ?
N1 H1 0.88(3) . ?
C8 C9 1.318(3) . ?
C8 C7 1.369(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9300 . ?
C10 C5 1.369(3) . ?
C10 H10 0.9300 . ?
C5 C6 1.329(3) . ?
C5 C4 1.455(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C1 C2 1.511(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?

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
N3 C3 C2 179.1(3) . . ?
C8 O2 C11 121.26(19) . . ?
C4 N2 N1 117.97(18) . . ?
C1 N1 N2 123.73(18) . . ?
C1 N1 H1 119.5(18) . . ?
N2 N1 H1 115.5(18) . . ?
C9 C8 O2 123.8(2) . . ?
C9 C8 C7 116.7(2) . . ?
O2 C8 C7 119.4(2) . . ?
C8 C9 C10 119.0(2) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C5 C10 C9 125.1(2) . . ?
C5 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
C6 C5 C10 114.7(2) . . ?
C6 C5 C4 122.2(2) . . ?
C10 C5 C4 123.0(2) . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 123.6(2) . . ?
C8 C7 H7 118.2 . . ?
C6 C7 H7 118.2 . . ?
N2 C4 C5 125.6(2) . . ?
N2 C4 H4 117.2 . . ?
C5 C4 H4 117.2 . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C1 N1 123.2(2) . . ?
O1 C1 C2 119.6(2) . . ?
N1 C1 C2 117.20(19) . . ?
C3 C2 C1 116.37(19) . . ?
C3 C2 H2A 108.2 . . ?
C1 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.88(3) 1.85(3) 2.711(2) 167(3) 4_545 yes
C9 H9 O2 0.93 2.40 3.300(3) 163.6 6_656 yes

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033

