Synthesis of orthogonal push-pull chromophores <i>via</i> click reaction of arylynamines.
Huang, Shuangping; Ma, Jing; Yi, Yikun; Li, Mingtao; Cai, Ping; Wu, Na; Organic & biomolecular chemistry 20 (2022) 4081–4085; doi:10.1039/d2ob00677d

data_7158661
_publ_section_title
;
 Synthesis of orthogonal push-pull chromophores <i>via</i> click reaction
 of arylynamines.
;
_journal_issue                   20
_journal_name_full               'Organic &amp; 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       '\f and \w 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/[\s^2^(Fo^2^)+(0.0772P)^2^] where P=(Fo^2^+2Fc^2^)/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 > 2\s(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
_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)
;
_shelx_res_checksum              39361
_olex2_submission_special_instructions 'No special instructions were received'