#------------------------------------------------------------------------------
#$Date: 2022-06-06 05:06:39 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275831 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158661.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_7158661
loop_
_publ_author_name
'Huang, Shuangping'
'Ma, Jing'
'Yi, Yikun'
'Li, Mingtao'
'Cai, Ping'
'Wu, Na'
_publ_section_title
;
 Synthesis of orthogonal push-pull chromophores via click reaction
 of arylynamines.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4081
_journal_page_last               4085
_journal_paper_doi               10.1039/d2ob00677d
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C22 H11 N5'
_chemical_formula_sum            'C22 H11 N5'
_chemical_formula_weight         345.36
_chemical_melting_point          421.25
_chemical_name_common
2-(4-(3,3-dicyano-1-(1H-indol-1-yl)allylidene)cyclohexa-2,5-dien-1-ylidene)malononitrile
_chemical_name_systematic        'MJ 2-12-1'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc269j9c
_audit_creation_date             2019-07-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-10-01 deposited with the CCDC.	2022-04-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.689(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.161(3)
_cell_length_b                   11.810(2)
_cell_length_c                   18.957(3)
_cell_measurement_reflns_used    5191
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.561
_cell_measurement_theta_min      2.517
_cell_volume                     3555.4(11)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1714
_diffrn_reflns_av_unetI/netI     0.0761
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21880
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.460
_diffrn_reflns_theta_min         2.149
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_description       block
_exptl_crystal_F_000             1424
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: ethyl acetate, n-hexane'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3669
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.946
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0532
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0772P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1293
_refine_ls_wR_factor_ref         0.1459
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2348
_reflns_number_total             3669
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00677d2.cif
_cod_data_source_block           2-12-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '148.1 oC' was changed to
'421.25' -- it was converted from degrees Celsius (C) to kelvins (K).

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7158661.cif.
;
_cod_original_cell_volume        3555.4(10)
_cod_database_code               7158661
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C15(H15), C16(H16),
 C18(H18), C19(H19)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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 0.07555(11) 1.11038(15) 0.02759(9) 0.0893(5) Uani 1 1 d . . . . .
N2 N 0.29027(10) 0.96223(14) 0.16426(9) 0.0848(5) Uani 1 1 d . . . . .
N3 N 0.17713(7) 0.75431(11) 0.20884(7) 0.0612(4) Uani 1 1 d . . . . .
N4 N -0.02931(13) 0.16237(18) 0.15992(12) 0.1078(6) Uani 1 1 d . . . . .
N5 N -0.18643(15) 0.3339(2) -0.02113(11) 0.1187(8) Uani 1 1 d . . . . .
C1 C 0.24877(10) 0.68893(14) 0.20764(9) 0.0652(4) Uani 1 1 d . . . . .
H1 H 0.257420 0.642768 0.169925 0.078 Uiso 1 1 calc R . . . .
C2 C 0.30314(10) 0.70336(14) 0.26962(10) 0.0661(4) Uani 1 1 d . . . . .
H2 H 0.356096 0.670274 0.281753 0.079 Uiso 1 1 calc R . . . .
C3 C 0.26581(9) 0.77802(13) 0.31358(9) 0.0593(4) Uani 1 1 d . . . . .
C4 C 0.28913(12) 0.82060(17) 0.38324(10) 0.0761(5) Uani 1 1 d . . . . .
H4 H 0.340687 0.800991 0.411192 0.091 Uiso 1 1 calc R . . . .
C5 C 0.23518(13) 0.89166(18) 0.41001(10) 0.0852(6) Uani 1 1 d . . . . .
H5 H 0.250460 0.919354 0.456532 0.102 Uiso 1 1 calc R . . . .
C6 C 0.15863(12) 0.92282(16) 0.36919(10) 0.0797(5) Uani 1 1 d . . . . .
H6 H 0.123761 0.971889 0.388554 0.096 Uiso 1 1 calc R . . . .
C7 C 0.13310(10) 0.88294(15) 0.30084(9) 0.0672(4) Uani 1 1 d . . . . .
H7 H 0.081626 0.904044 0.273341 0.081 Uiso 1 1 calc R . . . .
C8 C 0.18720(9) 0.80957(13) 0.27409(8) 0.0565(4) Uani 1 1 d . . . . .
C9 C 0.22033(11) 0.95102(14) 0.14187(9) 0.0626(4) Uani 1 1 d . . . . .
C10 C 0.13283(10) 0.94423(13) 0.11046(8) 0.0595(4) Uani 1 1 d . . . . .
C11 C 0.10123(11) 1.03777(16) 0.06501(9) 0.0685(5) Uani 1 1 d . . . . .
C12 C 0.08118(10) 0.85654(13) 0.11680(9) 0.0634(4) Uani 1 1 d . . . . .
H12 H 0.025720 0.863328 0.092850 0.076 Uiso 1 1 calc R . . . .
C13 C 0.10258(9) 0.75439(14) 0.15636(8) 0.0608(4) Uani 1 1 d . . . . .
C14 C 0.05542(10) 0.65597(14) 0.14325(8) 0.0618(4) Uani 1 1 d . . . . .
C15 C 0.07798(10) 0.55589(15) 0.18515(9) 0.0659(4) Uani 1 1 d . . . . .
H15 H 0.121653 0.559435 0.224660 0.079 Uiso 1 1 calc R . . . .
C16 C 0.03783(10) 0.45728(14) 0.16893(9) 0.0657(4) Uani 1 1 d . . . . .
H16 H 0.053923 0.394204 0.197569 0.079 Uiso 1 1 calc R . . . .
C17 C -0.02932(10) 0.44731(14) 0.10836(9) 0.0640(4) Uani 1 1 d . . . . .
C18 C -0.05481(10) 0.54840(15) 0.06823(10) 0.0718(5) Uani 1 1 d . . . . .
H18 H -0.099907 0.545174 0.029862 0.086 Uiso 1 1 calc R . . . .
C19 C -0.01537(10) 0.64732(15) 0.08456(10) 0.0703(5) Uani 1 1 d . . . . .
H19 H -0.033858 0.711401 0.057702 0.084 Uiso 1 1 calc R . . . .
C20 C -0.04703(12) 0.24433(19) 0.12885(12) 0.0807(5) Uani 1 1 d . . . . .
C21 C -0.06943(11) 0.34574(16) 0.08931(9) 0.0701(5) Uani 1 1 d . . . . .
C22 C -0.13544(14) 0.33836(18) 0.02864(11) 0.0842(6) 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
C1 N3 C13 126.19(13) . . ?
C8 N3 C1 108.41(12) . . ?
C8 N3 C13 125.01(13) . . ?
C2 C1 N3 109.03(15) . . ?
C1 C2 C3 108.17(14) . . ?
C4 C3 C2 135.01(15) . . ?
C4 C3 C8 117.92(16) . . ?
C8 C3 C2 107.05(14) . . ?
C5 C4 C3 119.37(16) . . ?
C4 C5 C6 121.30(18) . . ?
C7 C6 C5 121.33(18) . . ?
C6 C7 C8 117.38(15) . . ?
N3 C8 C3 107.32(13) . . ?
N3 C8 C7 130.01(14) . . ?
C7 C8 C3 122.68(15) . . ?
N2 C9 C10 175.72(19) . . ?
C9 C10 C11 114.88(14) . . ?
C12 C10 C9 125.86(15) . . ?
C12 C10 C11 119.14(14) . . ?
N1 C11 C10 178.40(18) . . ?
C10 C12 C13 126.96(14) . . ?
N3 C13 C12 117.51(13) . . ?
C14 C13 N3 119.61(13) . . ?
C14 C13 C12 122.83(13) . . ?
C13 C14 C15 121.14(14) . . ?
C13 C14 C19 121.86(14) . . ?
C15 C14 C19 116.90(14) . . ?
C16 C15 C14 121.79(15) . . ?
C15 C16 C17 121.20(15) . . ?
C16 C17 C18 117.23(14) . . ?
C21 C17 C16 122.08(16) . . ?
C21 C17 C18 120.68(15) . . ?
C19 C18 C17 121.72(15) . . ?
C18 C19 C14 120.99(16) . . ?
N4 C20 C21 179.3(2) . . ?
C17 C21 C20 122.18(16) . . ?
C17 C21 C22 120.78(17) . . ?
C22 C21 C20 117.04(16) . . ?
N5 C22 C21 177.8(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
N1 C11 1.141(2) . ?
N2 C9 1.139(2) . ?
N3 C1 1.3954(19) . ?
N3 C8 1.381(2) . ?
N3 C13 1.4130(18) . ?
N4 C20 1.142(3) . ?
N5 C22 1.133(3) . ?
C1 C2 1.341(2) . ?
C2 C3 1.422(3) . ?
C3 C4 1.398(2) . ?
C3 C8 1.400(2) . ?
C4 C5 1.373(3) . ?
C5 C6 1.382(3) . ?
C6 C7 1.368(2) . ?
C7 C8 1.392(2) . ?
C9 C10 1.431(2) . ?
C10 C11 1.435(2) . ?
C10 C12 1.349(2) . ?
C12 C13 1.429(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.433(2) . ?
C14 C19 1.444(2) . ?
C15 C16 1.341(2) . ?
C16 C17 1.431(2) . ?
C17 C18 1.434(2) . ?
C17 C21 1.379(2) . ?
C18 C19 1.339(2) . ?
C20 C21 1.424(3) . ?
C21 C22 1.419(3) . ?
