#------------------------------------------------------------------------------
#$Date: 2020-04-16 06:20:03 +0300 (Thu, 16 Apr 2020) $
#$Revision: 250832 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240322.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_7240322
loop_
_publ_author_name
'Zhang, Zhenfeng'
_publ_section_title
;
 An X-shaped cyano-carbonyl interaction on the polar surface of
 (cyanoacetyl)hydrazones
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE00359J
_journal_year                    2020
_chemical_formula_moiety         'C11 H11 N3 O2'
_chemical_formula_sum            'C11 H11 N3 O2'
_chemical_formula_weight         217.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-05 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.6847(17)
_cell_length_b                   9.1876(18)
_cell_length_c                   27.083(5)
_cell_measurement_reflns_used    1627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.68
_cell_volume                     2161.0(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            10907
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.046
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_min         1.504
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_description       prism
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.0049(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0436
_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)+(0.0561P)²+0.6848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1231
_reflns_number_total             1911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce00359j10.cif
_cod_data_source_block           II
_cod_database_code               7240322
_shelx_shelxl_version_number     2018/3
_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   0.972
_shelx_estimated_absorpt_t_max   0.981
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'
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 . . . . .
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
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_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_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
