One-step synthesis of conjugated enynenitriles from bromocyanoacetylene.
Ligny, Romain; Gauthier, Etienne S.; Yáñez, Manuel; Roisnel, Thierry; Guillemin, Jean-Claude; Trolez, Yann; Organic & biomolecular chemistry  (2017) –; doi:10.1039/c6ob02590k

data_7155755
_publ_section_title
;
 One-step synthesis of conjugated enynenitriles from bromocyanoacetylene.
;
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_paper_doi               10.1039/c6ob02590k
_journal_year                    2017
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C3 Br N'
_chemical_formula_sum            'C3 Br N'
_chemical_formula_weight         129.95
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_audit_update_record
;
2016-11-10 deposited with the CCDC.
2017-06-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.735(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.0950(10)
_cell_length_b                   6.1734(13)
_cell_length_c                   6.2035(14)
_cell_measurement_reflns_used    2292
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.30
_cell_measurement_wavelength     0.71073
_cell_volume                     194.14(7)
_computing_cell_refinement       'APEX3 (Bruker, 2015); SAINT (Bruker, 2014)'
_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_molecular_graphics    'SXGRAPH (Farrugia, 1999), Mercury (CSD, 2014)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            1670
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         3.301
_exptl_absorpt_coefficient_mu    10.357
_exptl_absorpt_correction_T_max  0.394
_exptl_absorpt_correction_T_min  0.118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.223
_exptl_crystal_description       block
_exptl_crystal_F_000             120
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.553
_refine_diff_density_min         -1.115
_refine_diff_density_rms         0.247
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.217
_refine_ls_matrix_type           full
_refine_ls_number_parameters     31
_refine_ls_number_reflns         486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.217
_refine_ls_R_factor_all          0.0300
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0405P)^2^+0.0220P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0719
_reflns_number_gt                471
_reflns_number_total             486
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob02590k2.cif
_cod_data_source_block           YT_BRC3N
_cod_database_code               7155755
_shelx_res_checksum              58305