#------------------------------------------------------------------------------
#$Date: 2020-08-06 15:48:01 +0300 (Thu, 06 Aug 2020) $
#$Revision: 254865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/66/7126673.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_7126673
loop_
_publ_author_name
'Bao, Wen'
'Gao, Zhu-Peng'
'Jin, Da-Ping'
'Xue, Cao-Gen'
'Liang, Huan'
'Lei, Ling-Sheng'
'Xu, Xue-Tao'
'Zhang, Kun'
'Wang, Shao-Hua'
_publ_section_title
;
 Direct synthesis of 2-substituted benzonitriles via alkylcyanation of
 arynes with N,N-disubstituted aminomalononitriles.
;
_journal_issue                   55
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              7641
_journal_page_last               7644
_journal_paper_doi               10.1039/d0cc01591a
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C17 H13 N3'
_chemical_formula_sum            'C17 H13 N3'
_chemical_formula_weight         259.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-10-31
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-10-31 deposited with the CCDC.	2020-05-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.191(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4918(5)
_cell_length_b                   10.0409(5)
_cell_length_c                   16.7446(7)
_cell_measurement_reflns_used    1363
_cell_measurement_temperature    295.72(11)
_cell_measurement_theta_max      25.9170
_cell_measurement_theta_min      4.2270
_cell_volume                     1405.21(13)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.72(11)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   57.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -99.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  3 omega   -9.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   30.0000 105
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0362642000
_diffrn_orient_matrix_UB_12      -0.0190443000
_diffrn_orient_matrix_UB_13      0.0333143000
_diffrn_orient_matrix_UB_21      -0.0718154000
_diffrn_orient_matrix_UB_22      0.0320723000
_diffrn_orient_matrix_UB_23      -0.0182413000
_diffrn_orient_matrix_UB_31      -0.0269575000
_diffrn_orient_matrix_UB_32      -0.0599557000
_diffrn_orient_matrix_UB_33      -0.0203131000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5744
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         3.557
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0543
_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)+(0.0453P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1426
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1855
_reflns_number_total             2772
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc01591a2.cif
_cod_data_source_block           baowen_1030
_cod_depositor_comments
'Adding full bibliography for 7126672--7126675.cif.'
_cod_original_cell_volume        1405.22(12)
_cod_database_code               7126673
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.987
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C1(H1a,H1b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C12(H12), C13(H13), C15(H15), C14(H14), C5(H5), C6(H6)
;
_olex2_date_sample_data_collection 2018-10-31
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.8892(2) 0.18291(16) 0.07704(9) 0.0466(4) Uani 1 1 d . . . . .
C16 C 0.6976(2) 0.35437(19) -0.06531(11) 0.0450(5) Uani 1 1 d . . . . .
C9 C 0.8116(2) 0.31041(19) 0.08158(10) 0.0449(5) Uani 1 1 d . . . . .
H9 H 0.889339 0.379671 0.074610 0.054 Uiso 1 1 calc R . . . .
C11 C 0.6696(2) 0.32576(19) 0.01283(11) 0.0455(5) Uani 1 1 d . . . . .
C8 C 1.0442(2) 0.1620(2) 0.12191(10) 0.0447(5) Uani 1 1 d . . . . .
C17 C 0.8584(3) 0.3750(2) -0.07877(11) 0.0492(5) Uani 1 1 d . . . . .
C3 C 1.0729(3) 0.0259(2) 0.13248(11) 0.0521(5) Uani 1 1 d . . . . .
C7 C 1.1613(2) 0.2548(2) 0.15054(11) 0.0526(5) Uani 1 1 d . . . . .
H7 H 1.141204 0.345670 0.144553 0.063 Uiso 1 1 calc R . . . .
C4 C 1.2221(3) -0.0180(3) 0.16857(13) 0.0676(7) Uani 1 1 d . . . . .
H4 H 1.243215 -0.108713 0.174014 0.081 Uiso 1 1 calc R . . . .
N3 N 0.9856(3) 0.39404(19) -0.08954(11) 0.0652(6) Uani 1 1 d . . . . .
C10 C 0.7643(3) 0.3322(2) 0.16223(13) 0.0601(6) Uani 1 1 d . . . . .
C2 C 0.9240(3) -0.0491(2) 0.09669(13) 0.0619(6) Uani 1 1 d . . . . .
H2A H 0.898618 -0.116634 0.133857 0.074 Uiso 1 1 calc R . . . .
H2B H 0.935291 -0.091098 0.045827 0.074 Uiso 1 1 calc R . . . .
C12 C 0.5134(3) 0.3084(2) 0.02355(14) 0.0613(6) Uani 1 1 d . . . . .
H12 H 0.492279 0.289477 0.074984 0.074 Uiso 1 1 calc R . . . .
C1 C 0.7967(3) 0.0596(2) 0.08346(14) 0.0617(6) Uani 1 1 d . . . . .
H1A H 0.720121 0.043947 0.034098 0.074 Uiso 1 1 calc R . . . .
H1B H 0.740111 0.064434 0.128877 0.074 Uiso 1 1 calc R . . . .
C13 C 0.3885(3) 0.3188(3) -0.04095(16) 0.0725(7) Uani 1 1 d . . . . .
H13 H 0.284050 0.306584 -0.032580 0.087 Uiso 1 1 calc R . . . .
C15 C 0.5704(3) 0.3650(2) -0.13035(13) 0.0602(6) Uani 1 1 d . . . . .
H15 H 0.589757 0.384027 -0.182095 0.072 Uiso 1 1 calc R . . . .
C14 C 0.4163(3) 0.3471(2) -0.11749(15) 0.0700(7) Uani 1 1 d . . . . .
H14 H 0.331079 0.354109 -0.160573 0.084 Uiso 1 1 calc R . . . .
C5 C 1.3408(3) 0.0740(3) 0.19678(14) 0.0728(7) Uani 1 1 d . . . . .
H5 H 1.441751 0.044888 0.221365 0.087 Uiso 1 1 calc R . . . .
C6 C 1.3096(3) 0.2078(3) 0.18850(13) 0.0651(7) Uani 1 1 d . . . . .
H6 H 1.389597 0.268434 0.208747 0.078 Uiso 1 1 calc R . . . .
N2 N 0.7321(3) 0.3462(2) 0.22482(12) 0.0919(8) Uani 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'
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
C9 N1 C1 118.89(17) . . ?
C8 N1 C9 119.62(15) . . ?
C8 N1 C1 107.09(16) . . ?
C11 C16 C17 119.92(17) . . ?
C15 C16 C11 120.6(2) . . ?
C15 C16 C17 119.48(18) . . ?
N1 C9 H9 107.4 . . ?
N1 C9 C11 110.93(15) . . ?
N1 C9 C10 112.04(16) . . ?
C11 C9 H9 107.4 . . ?
C10 C9 H9 107.4 . . ?
C10 C9 C11 111.49(17) . . ?
C16 C11 C9 119.05(18) . . ?
C12 C11 C16 118.23(18) . . ?
C12 C11 C9 122.69(18) . . ?
C3 C8 N1 109.82(18) . . ?
C7 C8 N1 128.94(19) . . ?
C7 C8 C3 121.18(19) . . ?
N3 C17 C16 178.7(2) . . ?
C8 C3 C2 108.98(18) . . ?
C4 C3 C8 119.7(2) . . ?
C4 C3 C2 131.3(2) . . ?
C8 C7 H7 121.1 . . ?
C8 C7 C6 117.8(2) . . ?
C6 C7 H7 121.1 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
N2 C10 C9 177.8(2) . . ?
C3 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C3 C2 C1 102.93(17) . . ?
H2A C2 H2B 109.1 . . ?
C1 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
N1 C1 C2 103.75(18) . . ?
N1 C1 H1A 111.0 . . ?
N1 C1 H1B 111.0 . . ?
C2 C1 H1A 111.0 . . ?
C2 C1 H1B 111.0 . . ?
H1A C1 H1B 109.0 . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C16 C15 H15 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C14 C15 H15 120.2 . . ?
C13 C14 C15 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5 119.9 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
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
N1 C9 1.448(2) . ?
N1 C8 1.411(2) . ?
N1 C1 1.480(3) . ?
C16 C11 1.400(3) . ?
C16 C17 1.437(3) . ?
C16 C15 1.395(3) . ?
C9 H9 0.9800 . ?
C9 C11 1.520(3) . ?
C9 C10 1.491(3) . ?
C11 C12 1.381(3) . ?
C8 C3 1.394(3) . ?
C8 C7 1.385(3) . ?
C17 N3 1.143(3) . ?
C3 C4 1.376(3) . ?
C3 C2 1.502(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.390(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.387(4) . ?
C10 N2 1.138(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.525(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C13 H13 0.9300 . ?
C13 C14 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.375(3) . ?
C14 H14 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.372(4) . ?
C6 H6 0.9300 . ?
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
N1 C9 C11 C16 -76.2(2) . . . . ?
N1 C9 C11 C12 101.7(2) . . . . ?
N1 C8 C3 C4 174.39(17) . . . . ?
N1 C8 C3 C2 -3.6(2) . . . . ?
N1 C8 C7 C6 -175.44(18) . . . . ?
C16 C11 C12 C13 0.1(3) . . . . ?
C16 C15 C14 C13 -0.1(4) . . . . ?
C9 N1 C8 C3 158.97(16) . . . . ?
C9 N1 C8 C7 -23.8(3) . . . . ?
C9 N1 C1 C2 -166.87(16) . . . . ?
C9 C11 C12 C13 -177.79(19) . . . . ?
C11 C16 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 -0.2(4) . . . . ?
C8 N1 C9 C11 164.30(16) . . . . ?
C8 N1 C9 C10 -70.4(2) . . . . ?
C8 N1 C1 C2 -27.4(2) . . . . ?
C8 C3 C4 C5 2.4(3) . . . . ?
C8 C3 C2 C1 -13.4(2) . . . . ?
C8 C7 C6 C5 0.7(3) . . . . ?
C17 C16 C11 C9 -2.9(3) . . . . ?
C17 C16 C11 C12 179.10(18) . . . . ?
C17 C16 C15 C14 -179.1(2) . . . . ?
C3 C8 C7 C6 1.5(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C2 C1 N1 24.2(2) . . . . ?
C7 C8 C3 C4 -3.1(3) . . . . ?
C7 C8 C3 C2 178.98(17) . . . . ?
C4 C3 C2 C1 169.0(2) . . . . ?
C4 C5 C6 C7 -1.4(3) . . . . ?
C10 C9 C11 C16 158.20(18) . . . . ?
C10 C9 C11 C12 -23.9(3) . . . . ?
C2 C3 C4 C5 179.8(2) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C1 N1 C9 C11 -61.3(2) . . . . ?
C1 N1 C9 C10 64.0(2) . . . . ?
C1 N1 C8 C3 19.8(2) . . . . ?
C1 N1 C8 C7 -162.9(2) . . . . ?
C15 C16 C11 C9 177.97(18) . . . . ?
C15 C16 C11 C12 0.0(3) . . . . ?
