# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p21m-1 _database_code_depnum_ccdc_archive 'CCDC 893209' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Br N' _chemical_formula_weight 182.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/m loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' _cell_length_a 7.9465(14) _cell_length_b 8.1567(14) _cell_length_c 7.9743(14) _cell_angle_alpha 90.00 _cell_angle_beta 116.379(11) _cell_angle_gamma 90.00 _cell_volume 463.05(14) _cell_formula_units_Z 2 _cell_measurement_temperature 435(2) _cell_measurement_reflns_used 4620 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 25.68 _exptl_crystal_description ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.306 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 4.362 _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 435(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4620 _diffrn_reflns_av_R_equivalents 0.0429 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 25.68 _reflns_number_total 944 _reflns_number_gt 734 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0700P)^2^+0.3800P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 944 _refine_ls_number_parameters 59 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0613 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1459 _refine_ls_wR_factor_gt 0.1358 _refine_ls_goodness_of_fit_ref 1.123 _refine_ls_restrained_S_all 1.124 _refine_ls_shift/su_max 0.040 _refine_ls_shift/su_mean 0.010 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.35574(3) 0.2500 0.63203(3) 0.08100(8) Uani 1 2 d S . . C4 C 0.6150(4) 0.2500 0.2952(4) 0.0850(9) Uani 1 2 d SD . 1 C1 C 0.8686(3) 0.3155(3) 0.6332(3) 0.0801(9) Uiso 0.50 1 d PD . 1 C2 C 0.8894(6) 0.4354(3) 0.7831(4) 0.1150(14) Uiso 0.50 1 d PD . 1 H2A H 0.7734 0.4424 0.7927 0.173 Uiso 0.50 1 calc PR . 1 H2B H 0.9207 0.5412 0.7524 0.173 Uiso 0.50 1 calc PR . 1 H2C H 0.9875 0.3994 0.9005 0.173 Uiso 0.50 1 calc PR . 1 C3 C 0.8794(5) 0.1420(3) 0.6967(5) 0.1068(13) Uiso 0.50 1 d PD . 1 H3A H 1.0082 0.1071 0.7547 0.160 Uiso 0.50 1 calc PR . 1 H3B H 0.8086 0.0732 0.5909 0.160 Uiso 0.50 1 calc PR . 1 H3C H 0.8285 0.1341 0.7853 0.160 Uiso 0.50 1 calc PR . 1 N1 N 0.6725(3) 0.3452(3) 0.4754(3) 0.0634(7) Uani 0.50 1 d P . 1 H1A H 0.5899(19) 0.3234(6) 0.5191(11) 0.076 Uiso 0.50 1 calc PR . 1 H1B H 0.6625(4) 0.451(2) 0.4475(7) 0.076 Uiso 0.50 1 calc PR . 1 C6 C 0.7513(4) 0.2500 0.2120(4) 0.1380(16) Uani 1 2 d S . 1 H6A H 0.8239 0.1514 0.2473 0.207 Uiso 0.50 1 d P A 1 H6B H 0.8317 0.3434 0.2566 0.207 Uiso 0.50 1 d P B 1 H6C H 0.6821 0.2500 0.0779 0.207 Uiso 1 2 d S C 1 C5 C 0.4197(5) 0.2988(6) 0.1616(4) 0.107(2) Uani 0.50 1 d P . 1 H5A H 0.3723 0.2246 0.0573 0.161 Uiso 0.50 1 calc PR . 1 H5B H 0.4207 0.4082 0.1177 0.161 Uiso 0.50 1 calc PR . 1 H5C H 0.3406 0.2949 0.2240 0.161 Uiso 0.50 1 calc PR . 1 H1 H 0.9567(4) 0.311(4) 0.5910(6) 0.129 Uiso 0.50 1 d PD D 1 H4 H 0.623(3) 0.1473(4) 0.3391(11) 0.129 Uiso 0.50 1 d PD E 1 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 Br1 0.08761(10) 0.07064(14) 0.09980(12) 0.000 0.05523(8) 0.000 C4 0.1013(14) 0.0701(14) 0.0838(12) 0.000 0.0413(10) 0.000 N1 0.0584(9) 0.0667(13) 0.0656(11) -0.0022(11) 0.0278(7) -0.0029(10) C6 0.1217(15) 0.200(4) 0.1256(15) 0.000 0.0851(10) 0.000 C5 0.0884(17) 0.146(6) 0.0760(17) -0.017(2) 0.0255(13) -0.022(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C4 C6 1.501(5) . ? C4 C5 1.494(4) 4_565 ? C4 C5 1.494(4) . ? C4 N1 1.514(3) . ? C4 N1 1.514(3) 4_565 ? C4 H4 0.900(5) . ? C1 C2 1.495(4) . ? C1 C3 1.492(3) . ? C1 N1 1.526(3) . ? C1 H1 0.903(5) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? N1 H1A 0.8869 . ? N1 H1B 0.8869 . ? C6 H6A 0.9558 . ? C6 H6B 0.9555 . ? C6 H6C 0.9610 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? 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 C6 C4 C5 114.2(3) . 4_565 ? C6 C4 C5 114.2(3) . . ? C6 C4 N1 116.56(19) . . ? C5 C4 N1 126.4(3) 4_565 . ? C5 C4 N1 108.6(2) . . ? C6 C4 N1 116.56(19) . 4_565 ? C5 C4 N1 108.6(2) 4_565 4_565 ? C5 C4 N1 126.4(3) . 4_565 ? C6 C4 H4 103.6(14) . . ? C5 C4 H4 84.1(11) 4_565 . ? C5 C4 H4 113.2(13) . . ? N1 C4 H4 99.7(6) . . ? C2 C1 C3 112.3(2) . . ? C2 C1 N1 105.4(2) . . ? C3 C1 N1 108.3(2) . . ? C2 C1 H1 119.9(17) . . ? C3 C1 H1 98(2) . . ? N1 C1 H1 112.1(5) . . ? C4 N1 C1 117.9(2) . . ? C4 C6 H6A 109.2 . . ? C4 C6 H6B 109.2 . . ? H6A C6 H6B 110.2 . . ? C4 C6 H6C 108.9 . . ? H6A C6 H6C 107.5 . . ? H6B C6 H6C 111.8 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Br1 0.89 2.47 3.360(3) 177.2 . N1 H1B Br1 0.89 2.51 3.393(3) 178.1 3_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.509 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.077 data_337 _database_code_depnum_ccdc_archive 'CCDC 893210' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Br N' _chemical_formula_weight 182.11 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 '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' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.02330(10) _cell_length_b 8.3080(2) _cell_length_c 13.5868(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 905.66(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 8913 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 25.67 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 4.460 _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8913 _diffrn_reflns_av_R_equivalents 0.0206 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.67 _reflns_number_total 1711 _reflns_number_gt 1575 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0223P)^2^+0.2200P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0235(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.451(17) _refine_ls_number_reflns 1711 _refine_ls_number_parameters 85 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0187 _refine_ls_wR_factor_ref 0.0463 _refine_ls_wR_factor_gt 0.0446 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.061 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.26761(2) 0.24972(3) -0.134307(14) 0.04948(10) Uani 1 1 d . . . N1 N 0.1718(2) 0.1657(2) 0.09890(15) 0.0379(4) Uani 1 1 d . . . H1A H 0.063(3) 0.187(3) 0.1067(17) 0.045 Uiso 1 1 d . . . H1B H 0.185(3) 0.187(3) 0.0385(18) 0.045 Uiso 1 1 d . . . C1 C 0.1983(3) -0.0125(3) 0.11303(18) 0.0468(6) Uani 1 1 d D . . C2 C 0.0864(4) -0.0995(3) 0.0421(2) 0.0652(8) Uani 1 1 d . . . H2A H -0.0271 -0.0680 0.0533 0.098 Uiso 1 1 calc R . . H2B H 0.0972 -0.2135 0.0517 0.098 Uiso 1 1 calc R . . H2C H 0.1176 -0.0726 -0.0241 0.098 Uiso 1 1 calc R . . C3 C 0.3796(4) -0.0557(4) 0.1010(3) 0.0792(9) Uani 1 1 d . . . H3A H 0.3942 -0.1688 0.1126 0.119 Uiso 1 1 calc R . . H3B H 0.4450 0.0042 0.1475 0.119 Uiso 1 1 calc R . . H3C H 0.4150 -0.0301 0.0354 0.119 Uiso 1 1 calc R . . C4 C 0.2665(3) 0.2803(3) 0.1653(2) 0.0492(6) Uani 1 1 d D . . C5 C 0.2247(4) 0.2441(4) 0.27158(18) 0.0713(7) Uani 1 1 d . . . H5A H 0.2766 0.3227 0.3134 0.107 Uiso 1 1 calc R . . H5B H 0.2650 0.1388 0.2884 0.107 Uiso 1 1 calc R . . H5C H 0.1061 0.2478 0.2805 0.107 Uiso 1 1 calc R . . C6 C 0.2162(4) 0.4494(3) 0.1363(2) 0.0653(8) Uani 1 1 d . . . H6A H 0.2541 0.4713 0.0706 0.098 Uiso 1 1 calc R . . H6B H 0.2657 0.5252 0.1810 0.098 Uiso 1 1 calc R . . H6C H 0.0971 0.4591 0.1389 0.098 Uiso 1 1 calc R . . H4 H 0.3869 0.2573 0.1577 0.078 Uiso 1 1 d RD . . H1 H 0.1586 -0.0370 0.1785 0.078 Uiso 1 1 d RD . . 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 Br1 0.04335(13) 0.06378(16) 0.04133(13) 0.00346(13) 0.00159(7) -0.00330(19) N1 0.0389(9) 0.0401(10) 0.0348(9) -0.0005(8) 0.0029(9) 0.0000(8) C1 0.0529(15) 0.0389(12) 0.0485(14) 0.0035(11) 0.0055(12) 0.0041(11) C2 0.083(2) 0.0493(16) 0.0636(17) -0.0063(14) -0.0009(15) -0.0112(15) C3 0.0599(17) 0.0526(16) 0.125(3) 0.0060(19) 0.0070(19) 0.0158(14) C4 0.0420(11) 0.0520(15) 0.0535(12) -0.0100(11) 0.0008(9) -0.0056(11) C5 0.0899(18) 0.0786(18) 0.0455(13) -0.0118(16) -0.0150(11) -0.007(3) C6 0.080(2) 0.0474(15) 0.0684(18) -0.0097(12) 0.0100(18) -0.0105(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 1.508(3) . ? N1 C4 1.516(3) . ? C1 C3 1.507(4) . ? C1 C2 1.503(4) . ? C4 C5 1.512(4) . ? C4 C6 1.514(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 N1 C4 118.1(2) . . ? C3 C1 C2 113.1(2) . . ? C3 C1 N1 110.9(2) . . ? C2 C1 N1 107.8(2) . . ? C5 C4 C6 112.0(2) . . ? C5 C4 N1 109.4(2) . . ? C6 C4 N1 107.1(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Br1 0.90(3) 2.46(3) 3.353(2) 178(2) 4_455 N1 H1B Br1 0.85(2) 2.49(3) 3.334(2) 172(2) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.67 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.357 _refine_diff_density_min -0.414 _refine_diff_density_rms 0.043 data_p21 _database_code_depnum_ccdc_archive 'CCDC 893211' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H16 Br N' _chemical_formula_weight 182.11 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8586(5) _cell_length_b 8.0818(5) _cell_length_c 7.8918(5) _cell_angle_alpha 90.00 _cell_angle_beta 116.290(4) _cell_angle_gamma 90.00 _cell_volume 449.38(5) _cell_formula_units_Z 2 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4536 _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 25.68 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 188 _exptl_absorpt_coefficient_mu 4.494 _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.495 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 295(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4536 _diffrn_reflns_av_R_equivalents 0.0275 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1533 _reflns_number_gt 1270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.356(15) _refine_ls_number_reflns 1533 _refine_ls_number_parameters 84 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0308 _refine_ls_R_factor_gt 0.0230 _refine_ls_wR_factor_ref 0.0459 _refine_ls_wR_factor_gt 0.0453 _refine_ls_goodness_of_fit_ref 0.864 _refine_ls_restrained_S_all 0.898 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.35304(4) 0.241081(17) 0.63370(5) 0.04916(12) Uani 1 1 d . . . C4 C 0.6142(4) 0.2427(13) 0.2972(4) 0.0479(7) Uani 1 1 d D . . C3 C 0.8855(8) 0.1344(10) 0.7037(10) 0.0670(17) Uani 1 1 d . . . H3A H 0.7915 0.1119 0.7473 0.101 Uiso 1 1 calc R . . H3B H 1.0098 0.1181 0.8055 0.101 Uiso 1 1 calc R . . H3C H 0.8677 0.0607 0.6017 0.101 Uiso 1 1 calc R . . C1 C 0.8657(7) 0.3117(9) 0.6351(7) 0.0444(14) Uani 1 1 d D . . N1 N 0.6705(4) 0.3403(4) 0.4752(4) 0.0384(7) Uani 1 1 d . . . H1A H 0.653(5) 0.448(5) 0.439(5) 0.046 Uiso 1 1 d . . . H1B H 0.590(5) 0.331(4) 0.520(5) 0.046 Uiso 1 1 d . . . C6 C 0.7535(6) 0.2700(12) 0.2170(6) 0.078(2) Uani 1 1 d . . . H6A H 0.7155 0.2066 0.1031 0.117 Uiso 1 1 calc R . . H6B H 0.8776 0.2355 0.3075 0.117 Uiso 1 1 calc R . . H6C H 0.7563 0.3854 0.1892 0.117 Uiso 1 1 calc R . . C5 C 0.4163(6) 0.2927(5) 0.1617(6) 0.0650(16) Uani 1 1 d . . . H5A H 0.3320 0.2714 0.2175 0.098 Uiso 1 1 calc R . . H5B H 0.3763 0.2301 0.0471 0.098 Uiso 1 1 calc R . . H5C H 0.4141 0.4085 0.1339 0.098 Uiso 1 1 calc R . . C2 C 0.8832(7) 0.4282(6) 0.7940(6) 0.0679(13) Uani 1 1 d . . . H2A H 0.8755 0.5407 0.7523 0.102 Uiso 1 1 calc R . . H2B H 1.0029 0.4105 0.9020 0.102 Uiso 1 1 calc R . . H2C H 0.7820 0.4067 0.8279 0.102 Uiso 1 1 calc R . . H1 H 0.9618 0.3314 0.5842 0.081 Uiso 1 1 d RD . . H4 H 0.6197 0.1350 0.3289 0.081 Uiso 1 1 d RD . . 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 Br1 0.05466(18) 0.04247(17) 0.0616(2) -0.0024(5) 0.03600(16) -0.0006(6) C4 0.0556(18) 0.0422(16) 0.0461(18) 0.003(6) 0.0228(16) -0.001(6) C3 0.057(3) 0.062(5) 0.070(5) 0.007(4) 0.018(3) 0.004(3) C1 0.035(2) 0.053(3) 0.039(3) 0.002(2) 0.011(2) -0.0016(18) N1 0.0397(17) 0.0352(16) 0.045(2) 0.0002(15) 0.0225(16) -0.0015(13) C6 0.077(2) 0.103(6) 0.075(3) -0.020(4) 0.051(2) -0.002(3) C5 0.063(2) 0.083(5) 0.044(2) -0.006(2) 0.019(2) -0.011(2) C2 0.067(3) 0.073(4) 0.054(3) -0.008(3) 0.018(3) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C4 C5 1.500(5) . ? C4 C6 1.504(4) . ? C4 N1 1.497(7) . ? C4 H4 0.9017 . ? C3 C1 1.515(7) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C1 N1 1.512(6) . ? C1 C2 1.525(6) . ? C1 H1 1.0124 . ? N1 H1A 0.91(4) . ? N1 H1B 0.85(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? 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 C5 C4 C6 112.2(4) . . ? C5 C4 N1 108.0(5) . . ? C6 C4 N1 110.5(6) . . ? C5 C4 H4 111.4 . . ? C6 C4 H4 107.7 . . ? N1 C4 H4 106.9 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C3 C1 N1 110.4(4) . . ? C3 C1 C2 109.4(6) . . ? N1 C1 C2 106.3(4) . . ? C3 C1 H1 108.3 . . ? N1 C1 H1 107.7 . . ? C2 C1 H1 114.7 . . ? C1 N1 C4 118.1(3) . . ? C1 N1 H1A 112(2) . . ? C4 N1 H1A 105(2) . . ? C1 N1 H1B 108(2) . . ? C4 N1 H1B 112(2) . . ? H1A N1 H1B 100(3) . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A Br1 0.91(4) 2.43(4) 3.335(3) 173(3) 2_656 N1 H1B Br1 0.85(3) 2.51(4) 3.346(3) 168(3) . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.442 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.045