#------------------------------------------------------------------------------ #$Date: 2017-07-08 14:09:18 +0300 (Sat, 08 Jul 2017) $ #$Revision: 198578 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/57/7155755.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_7155755 loop_ _publ_author_name 'Ligny, Romain' 'Gauthier, Etienne S.' 'Y\'a\~nez, Manuel' 'Roisnel, Thierry' 'Guillemin, Jean-Claude' 'Trolez, Yann' _publ_section_title ; One-step synthesis of conjugated enynenitriles from bromocyanoacetylene. ; _journal_name_full 'Organic & 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 _chemical_name_systematic ; ? ; _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_file ; TITL import in P 21/m job.res created by SHELXL-2016/6 at 14:16:57 on 09-Nov-2016 CELL 0.71073 5.0950 6.1734 6.2035 90.000 95.735 90.000 ZERR 2.00 0.0010 0.0013 0.0014 0.000 0.009 0.000 LATT 1 SYMM - X, 1/2 + Y, - Z SFAC C N BR UNIT 6 2 2 MERG 2 FMAP 2 PLAN 20 ACTA CONF LIST 4 WPDB -2 L.S. 4 TEMP 21.00 WGHT 0.040500 0.022000 FVAR 1.13424 C1 1 0.034740 0.250000 0.740539 10.50000 0.02273 0.01698 = 0.02180 0.00000 0.00338 0.00000 C2 1 -0.109765 0.250000 0.880473 10.50000 0.02474 0.01930 = 0.02146 0.00000 0.00488 0.00000 C3 1 -0.281079 0.250000 1.038960 10.50000 0.02641 0.02060 = 0.02209 0.00000 0.00499 0.00000 N4 2 -0.423352 0.250000 1.172092 10.50000 0.03486 0.03312 = 0.02823 0.00000 0.01327 0.00000 BR1 3 0.247082 0.250000 0.527850 10.50000 0.02149 0.01920 = 0.02002 0.00000 0.00735 0.00000 HKLF 4 REM import in P 21/m REM R1 = 0.0289 for 471 Fo > 4sig(Fo) and 0.0300 for all 486 data REM 31 parameters refined using 0 restraints END WGHT 0.0384 0.0218 REM Highest difference peak 0.553, deepest hole -1.115, 1-sigma level 0.247 Q1 1 0.3288 0.2500 0.6688 10.50000 0.05 0.55 Q2 1 -0.1812 -0.0234 0.8419 11.00000 0.05 0.54 Q3 1 -0.0189 -0.0106 0.8027 11.00000 0.05 0.53 Q4 1 -0.5403 -0.0104 1.3377 11.00000 0.05 0.52 Q5 1 0.1868 0.0673 0.4202 11.00000 0.05 0.49 Q6 1 -0.5094 -0.0290 1.2413 11.00000 0.05 0.49 Q7 1 -0.4001 0.0260 1.2599 11.00000 0.05 0.48 Q8 1 -0.1096 0.0275 0.6734 11.00000 0.05 0.46 Q9 1 -0.3371 -0.0381 1.1474 11.00000 0.05 0.45 Q10 1 0.0395 -0.0278 0.6627 11.00000 0.05 0.45 Q11 1 -0.6194 0.0106 1.1151 11.00000 0.05 0.44 Q12 1 -0.1049 0.0089 0.9656 11.00000 0.05 0.42 Q13 1 0.1837 0.0371 0.2858 11.00000 0.05 0.42 Q14 1 -0.4011 -0.0191 1.0815 11.00000 0.05 0.42 Q15 1 -0.2694 -0.0263 1.0137 11.00000 0.05 0.41 Q16 1 0.1651 0.2500 0.3834 10.50000 0.05 0.35 Q17 1 0.3180 0.0660 0.4224 11.00000 0.05 0.34 Q18 1 0.2711 -0.0018 0.3245 11.00000 0.05 0.33 Q19 1 0.1281 0.0084 0.8359 11.00000 0.05 0.32 Q20 1 0.2239 0.0225 0.5986 11.00000 0.05 0.32 ; _shelx_res_checksum 58305 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' 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 C1 C 0.0347(8) 0.250000 0.7405(7) 0.0204(8) Uani 1 2 d S T P C2 C -0.1098(9) 0.250000 0.8805(7) 0.0217(9) Uani 1 2 d S T P C3 C -0.2811(8) 0.250000 1.0390(7) 0.0229(9) Uani 1 2 d S T P N4 N -0.4234(9) 0.250000 1.1721(7) 0.0314(9) Uani 1 2 d S T P Br1 Br 0.24708(6) 0.250000 0.52785(6) 0.0199(2) Uani 1 2 d S T P loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.023(2) 0.0170(17) 0.0218(19) 0.000 0.0034(15) 0.000 C2 0.025(2) 0.0193(19) 0.021(2) 0.000 0.0049(17) 0.000 C3 0.026(2) 0.021(2) 0.022(2) 0.000 0.0050(17) 0.000 N4 0.035(2) 0.033(2) 0.028(2) 0.000 0.0133(18) 0.000 Br1 0.0215(3) 0.0192(3) 0.0200(3) 0.000 0.00735(16) 0.000 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 C2 C1 Br1 179.1(4) C1 C2 C3 178.8(5) N4 C3 C2 179.7(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.193(7) C1 Br1 1.788(4) C2 C3 1.378(6) C3 N4 1.152(7)