Base controlled diverse reactivity of allyl cyanide for synthesis of multi-substituted benzenes.
Yadav, Pratik; Shaw, Ranjay; Elagamy, Amr; Kumar, Abhinav; Pratap, Ramendra; Organic & biomolecular chemistry 16 (2018) 5465–5473; doi:10.1039/c8ob01270a

data_7156309
_publ_section_title
;
 Base controlled diverse reactivity of allyl cyanide for synthesis of
 multi-substituted benzenes.
;
_journal_issue                   30
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              5465
_journal_page_last               5473
_journal_paper_doi               10.1039/c8ob01270a
_journal_volume                  16
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_sum            'C18 H17 Br N2'
_chemical_formula_weight         341.24
_chemical_name_common            biphenyl
_chemical_name_systematic
4'-Bromo-3-piperidin-1-yl-biphenyl-4-carbonitrile
_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'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-12-03 deposited with the CCDC.
2018-07-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.54(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.541(3)
_cell_length_b                   14.222(4)
_cell_length_c                   12.432(3)
_cell_measurement_reflns_used    292
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      29.8553
_cell_measurement_theta_min      3.0039
_cell_volume                     1579.7(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
;
_computing_molecular_graphics
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'
_computing_publication_material
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_computing_structure_refinement
;
 SHELXL-2014/7 (Sheldrick, 2014)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. H\"ubschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_structure_solution
; 
 SIR97- Altomare A., Burla M.C., Camalli M., Cascarano G.L., Giacovazzo C. , 
 Guagliardi A., Moliterni A.G.G., Polidori G.,Spagna R. 
 (1999) J. Appl. Cryst. 32, 115-119
;
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 15.9853
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1071
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       12
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_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            17476
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.497
_diffrn_reflns_theta_min         3.326
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET)
(compiled Jan 20 2011,15:58:25)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.020
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.674
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3887
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0650
_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^)+(0.0844P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1983
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2064
_reflns_number_total             3887
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ob01270a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7156309.cif.'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7156309
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.950
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              26164