#------------------------------------------------------------------------------ #$Date: 2016-11-09 04:05:35 +0200 (Wed, 09 Nov 2016) $ #$Revision: 188333 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/19/2241936.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2241936 loop_ _publ_author_name 'Navarrete Guit\'errez, Ang\'elica' 'Aguirre Hern\'andez, Gerardo' 'Bern\`es, Sylvain' _publ_section_title ; Crystal structures of p-substituted derivatives of 2,6-dimethylbromobenzene with {\scriptstyle{1\/over2}} {\/leq} Z' {\/leq} 4 ; _journal_coeditor_code IS5462 _journal_issue 12 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 1762 _journal_page_last 1767 _journal_paper_doi 10.1107/S2056989016017485 _journal_volume 72 _journal_year 2016 _chemical_formula_iupac 'C8 H8 Br N O2' _chemical_formula_moiety 'C8 H8 Br N O2' _chemical_formula_sum 'C8 H8 Br N O2' _chemical_formula_weight 230.06 _chemical_melting_point 478 _chemical_name_systematic 2-Bromo-1,3-dimethyl-5-nitrobenzene _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _cell_angle_alpha 93.498(4) _cell_angle_beta 99.284(4) _cell_angle_gamma 101.722(5) _cell_formula_units_Z 2 _cell_length_a 4.0502(5) _cell_length_b 9.3817(6) _cell_length_c 12.1823(5) _cell_measurement_reflns_used 2941 _cell_measurement_temperature 296.0(10) _cell_measurement_theta_max 71.4760 _cell_measurement_theta_min 3.7050 _cell_volume 445.20(7) _computing_cell_refinement ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_data_collection ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_data_reduction ; CrysAlis PRO (Rigaku OD, 2015) ; _computing_molecular_graphics ; XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2008) ; _computing_publication_material ; CifTab (Sheldrick, 2008) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015b) ; _computing_structure_solution ; SHELXT (Sheldrick, 2015a) ; _diffrn_ambient_temperature 296.0(10) _diffrn_detector_area_resol_mean 5.1980 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Rigaku OD SuperNova AtlasS2' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5640 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.666 _diffrn_reflns_theta_min 3.694 _exptl_absorpt_coefficient_mu 5.977 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.30430 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; (CrysAlis PRO; Rigaku OD, 2015) ; _exptl_crystal_colour 'pale yellow' _exptl_crystal_density_diffrn 1.716 _exptl_crystal_description block _exptl_crystal_F_000 228 _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.633 _refine_diff_density_min -0.589 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_constraints 0 _refine_ls_number_parameters 111 _refine_ls_number_reflns 1697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.069 _refine_ls_R_factor_all 0.0495 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+0.2116P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1215 _refine_ls_wR_factor_ref 0.1276 _reflns_number_gt 1503 _reflns_number_total 1697 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file is5462sup1.cif _cod_data_source_block 2 _cod_database_code 2241936 _shelx_hkl_file ; 0 0 -1 166.59 3.67 0 0 1 205.18 3.53 0 0 2 1427.52 11.98 0 0 -2 1298.23 15.12 0 0 -3 187.43 7.07 0 0 3 210.60 5.34 0 0 -4 575.22 15.97 0 0 -4 673.02 15.42 0 0 4 655.65 9.09 0 0 4 558.69 10.06 0 0 5 2030.36 30.32 0 0 5 2015.94 18.03 0 0 6 49.46 3.11 0 0 6 39.42 4.74 0 0 -6 54.33 6.18 0 0 -6 49.65 4.97 0 0 6 37.26 3.86 0 0 -6 51.56 5.99 0 0 7 84.30 7.48 0 0 -7 102.22 7.54 0 0 -7 102.08 9.90 0 0 7 80.24 6.47 0 0 8 267.65 14.40 0 0 -8 266.79 16.53 0 0 -9 113.88 10.97 0 0 9 116.14 10.20 0 0 -10 298.64 18.54 0 0 10 345.34 20.71 0 0 10 278.76 16.50 0 0 10 313.28 11.72 0 0 10 322.34 18.93 0 0 -10 334.57 19.80 0 0 11 143.84 7.98 0 0 11 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4 0.27 0.31 3 -9 3 0.27 0.42 3 -9 2 9.86 2.98 3 -9 2 15.62 2.58 3 -9 1 -0.01 0.66 3 -9 1 1.28 0.86 3 -9 0 17.61 4.50 3 -9 -1 2.29 1.32 3 -9 -1 0.38 1.26 3 -9 -2 28.29 3.89 3 -9 -2 25.32 5.01 3 -9 -3 14.42 2.70 -3 9 4 7.08 2.26 3 -9 -4 9.48 2.08 -3 9 5 18.87 3.57 -3 9 5 17.89 3.56 3 -9 -5 18.77 2.85 -3 9 6 1.34 0.75 -3 9 6 2.97 1.25 -3 9 6 2.56 1.15 3 -9 -6 3.02 1.03 -4 -4 -1 1.35 0.88 4 4 0 1.52 0.67 -4 -4 0 1.22 0.90 4 4 -1 8.84 2.25 -4 -4 1 3.73 1.32 -4 -4 1 7.71 2.01 4 4 -2 3.91 1.62 -4 -4 2 5.09 1.84 4 4 -3 4.62 1.70 -4 -4 3 5.38 1.82 4 4 -4 16.77 3.37 -4 -4 4 13.95 2.93 4 4 -5 5.70 1.83 -4 -4 5 7.12 1.98 4 4 -6 12.06 2.62 -4 -4 6 10.86 2.34 -4 -3 -3 1.27 1.10 4 3 2 24.27 3.90 -4 -3 -2 31.30 4.74 4 3 2 17.02 3.52 4 3 1 3.07 1.66 -4 -3 -1 3.57 1.94 4 3 0 8.13 2.72 -4 -3 0 8.58 2.82 4 3 -1 5.53 1.99 -4 -3 1 1.94 1.58 -4 -3 1 6.51 2.22 4 3 -2 0.23 0.52 -4 -3 2 2.60 1.42 -4 -3 2 3.25 2.09 4 3 -3 -1.26 1.46 -4 -3 3 1.62 1.29 4 3 -4 1.65 1.25 -4 -3 4 0.70 0.77 4 3 -5 9.34 2.64 -4 -3 5 9.19 2.65 4 3 -6 3.15 1.51 -4 -3 6 1.13 0.69 -4 -3 6 3.50 1.37 4 3 -7 4.67 1.72 -4 -3 7 9.91 2.36 -4 -3 7 8.18 2.09 4 3 -8 12.73 2.56 -4 -3 8 11.97 2.18 -4 -3 8 9.20 2.22 4 2 4 0.24 0.84 -4 -2 -4 1.72 1.38 4 2 4 -0.08 0.34 4 2 3 2.45 1.33 4 2 3 4.29 1.84 -4 -2 -3 5.93 2.35 4 2 2 1.56 1.03 -4 -2 -2 2.55 1.61 4 2 1 61.25 7.27 -4 -2 -1 56.21 5.47 4 2 0 6.67 2.43 -4 -2 0 8.92 2.61 4 2 -1 9.96 3.01 -4 -2 1 8.66 2.60 -4 -2 1 12.56 2.85 4 2 -2 19.25 4.35 -4 -2 2 16.76 3.86 -4 -2 2 16.69 3.22 4 2 -3 22.82 4.69 -4 -2 3 20.32 4.30 4 2 -4 67.71 8.11 -4 -2 4 66.02 7.75 4 2 -5 8.79 2.76 -4 -2 5 14.50 3.52 4 2 -6 4.14 1.83 -4 -2 6 5.35 2.11 -4 -2 6 5.00 1.90 -4 -2 7 6.02 2.14 -4 -2 7 7.08 2.27 4 2 -8 0.51 0.88 -4 -2 8 2.37 1.12 -4 -2 8 2.73 1.15 -4 -2 9 0.97 0.69 -4 -1 -5 1.51 1.47 -4 -1 -5 5.91 1.84 4 1 4 2.54 1.30 -4 -1 -4 2.09 1.49 4 1 3 6.84 2.21 -4 -1 -3 11.32 2.81 -4 -1 -3 6.83 2.27 -4 -1 -3 8.16 2.46 4 1 2 112.92 9.93 -4 -1 -2 109.61 8.16 -4 -1 -2 101.73 8.36 4 1 1 4.33 2.01 -4 -1 -1 3.85 1.79 -4 -1 -1 5.82 2.18 4 1 0 0.70 1.18 -4 -1 0 1.84 0.97 -4 -1 0 3.82 2.23 4 1 -1 1.40 0.34 -4 -1 1 1.16 1.24 -4 -1 1 0.30 1.01 -4 -1 1 3.25 1.87 4 1 -2 1.94 1.19 4 1 -2 -0.08 0.61 -4 -1 2 2.32 1.74 4 1 -3 -0.43 1.14 -4 -1 3 1.98 1.68 -4 -1 3 1.40 1.46 -4 -1 3 3.16 1.61 4 1 -3 0.52 0.48 4 1 -4 5.90 2.57 -4 -1 4 11.45 3.51 -4 -1 4 12.53 2.87 4 1 -5 54.23 7.40 -4 -1 5 59.38 7.40 -4 -1 6 14.50 3.75 4 1 -6 7.14 2.68 -4 -1 6 17.78 3.90 4 1 -7 9.85 2.82 -4 -1 7 35.33 5.15 4 1 -7 14.93 2.84 -4 -1 7 37.55 5.65 -4 -1 8 27.12 4.00 -4 -1 8 29.18 4.63 -4 -1 9 24.49 3.21 4 1 -9 13.53 2.41 -4 -1 9 24.10 3.80 4 1 -10 5.47 1.33 -4 -1 10 11.31 2.32 -4 0 -6 -0.31 0.58 -4 0 -6 1.00 1.11 -4 0 -5 1.57 1.02 -4 0 -5 0.28 0.88 -4 0 -5 1.60 1.40 -4 0 -5 2.02 1.12 4 0 4 3.05 1.44 4 0 4 2.22 1.13 -4 0 -4 4.12 1.85 -4 0 -4 4.89 2.24 -4 0 -4 4.67 1.85 4 0 3 -0.49 1.17 4 0 3 -0.75 1.11 -4 0 -3 0.48 1.06 -4 0 -3 0.83 1.44 -4 0 -3 1.13 1.54 4 0 2 11.79 3.27 4 0 2 10.85 2.56 -4 0 -2 11.15 2.57 -4 0 -2 9.79 3.22 -4 0 -2 11.15 3.07 4 0 1 74.74 8.33 -4 0 -1 97.26 7.89 -4 0 -1 81.40 8.80 -4 0 -1 81.17 7.70 4 0 1 77.05 6.93 4 0 0 16.84 4.26 -4 0 0 19.96 3.46 -4 0 0 19.16 4.08 -4 0 0 18.95 3.88 4 0 0 16.22 3.12 4 0 -1 49.43 6.95 -4 0 1 54.07 6.45 -4 0 1 52.01 6.13 4 0 -1 38.05 4.75 4 0 -2 31.38 5.63 -4 0 2 27.83 4.97 -4 0 2 35.03 5.18 -4 0 2 37.12 4.97 4 0 -2 24.35 3.75 4 0 -3 46.57 6.83 -4 0 3 45.63 6.69 -4 0 3 49.60 6.00 -4 0 3 54.05 5.71 4 0 -4 38.47 6.21 -4 0 4 45.15 6.71 -4 0 4 45.43 5.50 -4 0 5 7.99 3.11 4 0 -5 5.68 2.32 -4 0 5 5.16 2.16 -4 0 5 7.04 1.92 4 0 -5 4.41 1.77 -4 0 6 3.51 0.81 -4 0 6 5.88 2.44 4 0 -6 2.82 1.37 -4 0 7 0.63 0.51 -4 0 7 0.97 0.87 4 0 -7 0.53 0.70 -4 0 8 -0.28 0.56 4 0 -8 0.12 0.42 -4 0 9 8.50 2.56 -4 0 9 8.23 2.01 4 0 -9 2.87 1.27 -4 0 10 7.55 1.98 4 0 -10 5.61 1.51 -4 1 -6 11.33 2.68 -4 1 -6 9.20 2.47 4 -1 6 13.80 2.05 4 -1 5 8.18 1.92 -4 1 -5 11.55 2.68 -4 1 -5 10.42 3.17 -4 1 -5 7.95 1.91 4 -1 4 25.38 4.47 -4 1 -4 26.48 4.01 -4 1 -4 27.08 4.89 -4 1 -4 25.40 3.90 4 -1 4 18.54 3.19 4 -1 3 6.90 2.46 4 -1 3 6.47 1.92 -4 1 -3 6.58 2.15 -4 1 -3 6.85 2.19 -4 1 -3 7.49 2.31 4 -1 2 9.74 3.02 4 -1 2 12.47 2.76 -4 1 -2 14.19 2.79 -4 1 -2 12.39 2.99 4 -1 1 2.27 1.42 4 -1 1 2.00 1.36 -4 1 -1 3.33 1.50 -4 1 -1 0.99 0.79 4 -1 0 2.50 1.65 4 -1 0 2.21 1.18 -4 1 0 1.35 0.99 -4 1 0 0.79 0.34 4 -1 -1 2.72 1.95 -4 1 1 4.19 1.84 4 -1 -1 3.44 1.49 -4 1 1 6.07 1.91 4 -1 -2 12.94 3.60 -4 1 2 10.12 3.21 -4 1 2 13.73 3.22 -4 1 2 12.78 2.82 4 -1 -2 8.45 2.30 -4 1 3 15.10 3.77 -4 1 3 17.94 3.58 -4 1 3 16.59 3.05 4 -1 -3 11.26 2.56 -4 1 4 28.43 5.35 -4 1 4 30.82 4.56 -4 1 4 38.94 4.50 4 -1 -4 25.92 4.03 -4 1 5 60.00 7.56 -4 1 5 61.07 6.11 4 -1 -5 42.84 5.20 -4 1 6 48.06 6.58 -4 1 6 46.52 4.89 4 -1 -6 35.37 4.98 -4 1 7 98.30 8.80 4 -1 -7 50.32 5.88 -4 1 8 -0.34 0.42 -4 1 8 0.90 0.41 4 -1 -8 0.25 0.69 -4 1 9 42.07 4.57 -4 1 9 41.34 5.45 -4 1 10 15.18 2.77 4 -1 -10 10.45 2.10 4 -2 6 2.06 0.87 -4 2 -6 4.22 1.58 -4 2 -6 1.36 0.65 -4 2 -6 2.33 1.65 4 -2 5 1.70 0.98 -4 2 -5 0.59 1.18 -4 2 -5 -0.09 0.49 4 -2 4 2.60 1.57 4 -2 4 0.89 1.20 -4 2 -4 0.76 0.98 -4 2 -4 0.20 1.43 -4 2 -4 1.51 0.70 4 -2 3 37.05 5.66 -4 2 -3 41.84 5.01 -4 2 -3 43.63 5.26 4 -2 3 40.10 5.02 4 -2 2 32.41 5.32 -4 2 -2 30.29 4.49 -4 2 -2 41.83 5.22 4 -2 2 31.30 4.48 4 -2 1 33.32 5.65 -4 2 -1 37.84 5.13 -4 2 -1 39.54 5.18 4 -2 1 30.51 4.46 4 -2 0 64.56 7.70 -4 2 0 69.08 7.12 4 -2 0 47.50 5.29 -4 2 1 73.29 7.47 4 -2 -1 53.89 5.79 4 -2 -1 57.44 5.54 -4 2 2 2.80 1.42 -4 2 2 0.52 1.03 4 -2 -2 1.54 1.62 4 -2 -2 1.95 1.17 -4 2 3 39.28 6.31 -4 2 3 29.59 4.60 4 -2 -3 30.31 4.23 -4 2 4 17.96 4.25 -4 2 4 19.81 3.62 4 -2 -4 17.55 3.39 -4 2 5 9.44 3.01 -4 2 5 10.23 2.40 4 -2 -5 8.80 2.52 -4 2 6 1.38 1.33 -4 2 6 0.09 0.72 4 -2 -6 0.70 0.81 -4 2 7 73.43 7.60 4 -2 -7 45.11 5.53 -4 2 8 8.48 2.25 4 -2 -8 5.47 1.82 -4 2 9 1.34 0.86 4 -2 -9 0.38 0.31 -4 2 10 13.35 2.55 4 -2 -10 11.10 2.08 4 -3 6 3.76 1.03 -4 3 -6 4.32 2.09 4 -3 5 0.42 0.49 -4 3 -5 2.02 1.15 -4 3 -5 -0.62 1.73 -4 3 -4 28.23 3.82 4 -3 4 19.42 3.31 4 -3 3 9.92 2.93 4 -3 3 9.38 2.39 -4 3 -3 11.38 2.47 -4 3 -3 10.38 2.42 4 -3 2 1.14 1.00 -4 3 -2 -0.04 0.78 4 -3 1 0.38 0.57 -4 3 -1 0.84 0.27 4 -3 0 0.93 0.98 -4 3 0 -0.54 1.66 4 -3 0 0.68 0.69 -4 3 1 49.17 5.92 4 -3 -1 41.66 5.04 4 -3 -1 50.62 5.22 -4 3 2 28.11 5.23 4 -3 -2 19.13 3.26 4 -3 -2 22.19 3.62 -4 3 3 13.99 3.73 4 -3 -3 13.50 2.84 -4 3 4 32.65 5.80 4 -3 -4 28.43 4.24 -4 3 5 62.14 7.73 4 -3 -5 62.27 6.33 -4 3 6 69.10 7.80 4 -3 -6 58.88 6.21 -4 3 7 71.44 7.43 4 -3 -7 52.04 5.91 -4 3 8 1.83 1.19 4 -3 -8 0.89 0.81 -4 3 9 22.92 3.28 4 -3 -9 16.60 2.79 -4 3 10 6.24 1.83 4 -3 -10 4.92 1.21 4 -4 6 4.16 1.11 -4 4 -6 2.91 1.14 4 -4 5 4.45 1.43 4 -4 4 4.69 1.57 -4 4 -4 9.52 2.28 -4 4 -3 49.94 5.34 4 -4 3 43.42 4.79 4 -4 2 14.50 2.89 4 -4 2 14.25 2.70 -4 4 -1 31.70 4.55 4 -4 1 35.97 4.50 4 -4 1 36.73 4.38 -4 4 0 20.55 3.63 4 -4 0 18.05 3.23 4 -4 0 21.76 3.43 4 -4 -1 37.91 4.63 4 -4 -1 46.08 5.03 -4 4 2 6.82 2.69 4 -4 -2 4.92 1.65 4 -4 -2 5.29 1.81 -4 4 3 2.03 1.21 4 -4 -3 3.19 1.26 4 -4 -3 4.91 1.80 -4 4 4 1.05 1.16 4 -4 -4 1.16 0.80 -4 4 5 3.43 1.88 -4 4 5 2.41 1.26 4 -4 -5 4.44 1.53 -4 4 6 1.68 0.92 -4 4 6 1.73 1.00 4 -4 -6 0.75 0.96 -4 4 7 34.04 5.26 -4 4 7 29.70 4.54 4 -4 -7 25.57 3.82 -4 4 8 13.99 2.82 4 -4 -8 9.11 2.14 -4 4 9 21.33 2.96 4 -4 -9 18.68 2.67 4 -5 5 1.72 0.82 4 -5 4 0.30 0.77 4 -5 4 2.98 1.18 4 -5 3 0.18 0.32 -4 5 -3 0.01 1.09 4 -5 3 1.64 0.90 4 -5 2 1.85 1.11 4 -5 2 1.34 0.89 4 -5 1 21.58 3.58 4 -5 1 21.07 3.29 4 -5 0 11.27 2.39 4 -5 0 17.09 3.03 4 -5 -1 17.76 2.97 4 -5 -1 18.88 3.26 4 -5 -2 12.43 2.41 4 -5 -2 18.57 3.24 -4 5 3 28.35 5.15 4 -5 -3 33.00 3.99 4 -5 -3 43.72 4.94 -4 5 4 21.04 4.48 -4 5 4 19.47 4.22 4 -5 -4 26.36 3.52 4 -5 -4 30.17 4.17 -4 5 5 41.78 6.15 -4 5 5 33.47 5.36 4 -5 -5 52.63 5.82 4 -5 -5 49.85 5.35 -4 5 6 8.09 2.47 -4 5 6 7.34 2.42 4 -5 -6 6.53 2.09 4 -5 -6 6.19 1.80 -4 5 7 10.30 2.69 -4 5 7 11.40 2.66 4 -5 -7 5.96 1.75 4 -5 -7 9.13 2.09 -4 5 8 5.30 1.59 4 -5 -8 3.17 1.11 4 -5 -8 3.93 1.13 -4 5 9 0.75 0.61 4 -6 4 4.41 1.29 4 -6 3 6.08 1.60 4 -6 2 16.17 2.72 4 -6 1 110.58 7.43 4 -6 0 6.29 1.94 4 -6 -1 0.82 0.80 4 -6 -2 2.29 1.34 4 -6 -2 3.11 1.39 -4 6 3 1.40 0.69 4 -6 -3 0.22 0.44 4 -6 -3 0.18 0.39 -4 6 4 2.20 1.52 -4 6 4 2.48 1.20 4 -6 -4 4.52 1.65 4 -6 -4 4.56 1.52 -4 6 5 18.73 3.83 4 -6 -5 30.41 4.35 4 -6 -5 25.68 3.57 -4 6 6 16.00 3.32 -4 6 6 14.35 3.14 4 -6 -6 23.20 3.67 4 -6 -6 20.44 3.03 -4 6 7 14.22 2.88 -4 6 7 13.31 2.63 4 -6 -7 11.57 2.39 4 -6 -7 15.07 2.31 -4 6 8 11.88 2.13 4 -7 4 1.59 0.55 4 -7 3 1.86 0.89 4 -7 2 7.57 1.79 4 -7 1 46.53 4.52 4 -7 0 37.01 4.16 4 -7 -1 5.15 1.54 4 -7 -2 7.69 2.12 4 -7 -2 7.67 1.86 -4 7 3 10.24 2.70 4 -7 -3 15.68 2.97 4 -7 -3 18.99 3.01 -4 7 4 5.77 2.08 -4 7 4 6.50 2.20 4 -7 -4 15.91 2.98 4 -7 -4 14.86 2.58 -4 7 5 11.03 2.63 -4 7 5 10.71 2.56 4 -7 -5 27.20 3.78 4 -7 -5 30.34 3.47 -4 7 6 0.85 0.62 -4 7 6 0.08 0.49 4 -7 -6 0.54 0.71 -4 7 7 1.46 0.84 4 -8 2 1.84 0.87 4 -8 1 15.43 2.30 4 -8 0 4.13 1.24 4 -8 -1 0.09 0.47 4 -8 -2 -0.45 0.56 4 -8 -3 4.55 1.31 4 -8 -4 2.62 1.15 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 9299 _shelx_res_file ; nitro1c.res created by SHELXL-2014/7 TITL nitro1c in P-1 CELL 1.54184 4.0502 9.3817 12.1823 93.498 99.284 101.722 ZERR 2.00 0.0005 0.0006 0.0005 0.004 0.004 0.005 LATT 1 SFAC C H N O BR UNIT 16 16 4 4 2 ACTA L.S. 20 BOND $H CONF FMAP 2 PLAN 10 EQIV $1 -x+1, -y+1, -z EQIV $2 -x, -y+2, -z HTAB C4 O1_$1 HTAB C6 O2_$2 WGHT 0.068600 0.211600 FVAR 1.00303 BR1 5 0.116000 0.720523 0.459937 11.00000 0.08500 0.09978 = 0.05358 0.00408 0.01967 0.02069 N1 3 0.297657 0.762169 -0.022562 11.00000 0.07264 0.06016 = 0.05666 0.00870 0.01263 0.01512 O1 4 0.413095 0.669075 -0.067699 11.00000 0.13201 0.09301 = 0.06367 0.01169 0.03798 0.05060 O2 4 0.218231 0.863404 -0.070739 11.00000 0.14668 0.08410 = 0.07060 0.02913 0.03123 0.04881 C1 1 0.146808 0.863483 0.262662 11.00000 0.04809 0.06028 = 0.05872 -0.00573 0.00276 0.01504 C2 1 0.171401 0.733212 0.308630 11.00000 0.04722 0.06588 = 0.04751 0.00346 0.00869 0.01387 C3 1 0.232416 0.611676 0.249951 11.00000 0.05206 0.05838 = 0.05360 0.00445 0.00703 0.01322 C4 1 0.275175 0.623701 0.140643 11.00000 0.05695 0.04995 = 0.05412 0.00442 0.01025 0.01585 AFIX 43 H4A 2 0.321100 0.545869 0.099056 11.00000 -1.20000 AFIX 0 C5 1 0.249455 0.752006 0.093158 11.00000 0.05328 0.05394 = 0.05130 0.00401 0.00688 0.01032 C6 1 0.184599 0.871848 0.151749 11.00000 0.06091 0.04968 = 0.06061 0.00454 0.00438 0.01685 AFIX 43 H6A 2 0.166711 0.956425 0.117323 11.00000 -1.20000 AFIX 0 C7 1 0.087363 0.996158 0.326983 11.00000 0.08392 0.07222 = 0.07768 -0.01559 0.01019 0.02720 AFIX 137 H7A 2 -0.106796 0.967833 0.362959 11.00000 -1.50000 H7B 2 0.044471 1.067627 0.276471 11.00000 -1.50000 H7C 2 0.286661 1.037273 0.382368 11.00000 -1.50000 AFIX 0 C8 1 0.250180 0.470524 0.300777 11.00000 0.09049 0.06770 = 0.06365 0.01953 0.01553 0.02253 AFIX 137 H8A 2 0.402634 0.490713 0.371568 11.00000 -1.50000 H8B 2 0.333489 0.407670 0.251723 11.00000 -1.50000 H8C 2 0.025744 0.423183 0.311450 11.00000 -1.50000 AFIX 0 HKLF 4 REM nitro1c in P-1 REM R1 = 0.0449 for 1503 Fo > 4sig(Fo) and 0.0495 for all 1697 data REM 111 parameters refined using 0 restraints END WGHT 0.0690 0.2100 REM Highest difference peak 0.633, deepest hole -0.589, 1-sigma level 0.081 Q1 1 -0.1095 0.7379 0.4237 11.00000 0.05 0.63 Q2 1 0.3743 0.7177 0.4977 11.00000 0.05 0.55 Q3 1 -0.2727 0.7177 0.3030 11.00000 0.05 0.25 Q4 1 0.4065 1.1149 0.4765 11.00000 0.05 0.23 Q5 1 0.5641 0.7138 0.4452 11.00000 0.05 0.23 Q6 1 0.2246 0.6719 0.2810 11.00000 0.05 0.22 Q7 1 0.3739 0.7026 0.1274 11.00000 0.05 0.22 Q8 1 0.5389 0.4741 0.3513 11.00000 0.05 0.22 Q9 1 0.0408 0.8032 -0.0609 11.00000 0.05 0.22 Q10 1 -0.0269 0.8898 0.2342 11.00000 0.05 0.21 ; _shelx_res_checksum 22770 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy Br Br1 0.11600(12) 0.72052(5) 0.45994(3) 0.0787(2) Uani d 1 N N1 0.2977(9) 0.7622(4) -0.0226(3) 0.0628(8) Uani d 1 O O1 0.4131(11) 0.6691(4) -0.0677(3) 0.0899(10) Uani d 1 O O2 0.2182(11) 0.8634(4) -0.0707(3) 0.0947(11) Uani d 1 C C1 0.1468(9) 0.8635(4) 0.2627(3) 0.0565(8) Uani d 1 C C2 0.1714(9) 0.7332(4) 0.3086(3) 0.0534(8) Uani d 1 C C3 0.2324(9) 0.6117(4) 0.2500(3) 0.0548(8) Uani d 1 C C4 0.2752(9) 0.6237(4) 0.1406(3) 0.0530(8) Uani d 1 H H4A 0.3211 0.5459 0.0991 0.064 Uiso calc 1 C C5 0.2495(9) 0.7520(4) 0.0932(3) 0.0533(8) Uani d 1 C C6 0.1846(10) 0.8718(4) 0.1517(3) 0.0571(8) Uani d 1 H H6A 0.1667 0.9564 0.1173 0.069 Uiso calc 1 C C7 0.0874(12) 0.9962(5) 0.3270(4) 0.0779(12) Uani d 1 H H7A -0.1068 0.9678 0.3630 0.117 Uiso calc 1 H H7B 0.0445 1.0676 0.2765 0.117 Uiso calc 1 H H7C 0.2867 1.0373 0.3824 0.117 Uiso calc 1 C C8 0.2502(13) 0.4705(5) 0.3008(4) 0.0724(11) Uani d 1 H H8A 0.4026 0.4907 0.3716 0.109 Uiso calc 1 H H8B 0.3335 0.4077 0.2517 0.109 Uiso calc 1 H H8C 0.0257 0.4232 0.3114 0.109 Uiso calc 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0850(4) 0.0998(4) 0.0536(3) 0.0207(3) 0.0197(2) 0.0041(2) N1 0.073(2) 0.0602(17) 0.0567(17) 0.0151(15) 0.0126(15) 0.0087(14) O1 0.132(3) 0.093(2) 0.0637(18) 0.051(2) 0.0380(19) 0.0117(16) O2 0.147(3) 0.084(2) 0.071(2) 0.049(2) 0.031(2) 0.0291(17) C1 0.0481(17) 0.060(2) 0.059(2) 0.0150(15) 0.0028(14) -0.0057(16) C2 0.0472(17) 0.066(2) 0.0475(17) 0.0139(14) 0.0087(13) 0.0035(15) C3 0.0521(18) 0.0584(19) 0.0536(18) 0.0132(15) 0.0070(14) 0.0044(15) C4 0.0570(19) 0.0500(17) 0.0541(19) 0.0158(14) 0.0103(14) 0.0044(14) C5 0.0533(18) 0.0539(18) 0.0513(18) 0.0103(14) 0.0069(14) 0.0040(14) C6 0.061(2) 0.0497(18) 0.061(2) 0.0169(15) 0.0044(16) 0.0045(15) C7 0.084(3) 0.072(3) 0.078(3) 0.027(2) 0.010(2) -0.016(2) C8 0.090(3) 0.068(2) 0.064(2) 0.023(2) 0.016(2) 0.0195(19) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 '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 O1 N1 O2 122.2(4) O1 N1 C5 119.0(3) O2 N1 C5 118.7(3) C6 C1 C2 117.7(3) C6 C1 C7 118.6(4) C2 C1 C7 123.7(4) C1 C2 C3 123.8(3) C1 C2 Br1 117.9(3) C3 C2 Br1 118.4(3) C4 C3 C2 117.4(3) C4 C3 C8 119.8(3) C2 C3 C8 122.8(4) C3 C4 C5 119.7(3) C3 C4 H4A 120.2 C5 C4 H4A 120.2 C4 C5 C6 122.5(3) C4 C5 N1 118.6(3) C6 C5 N1 118.9(3) C5 C6 C1 118.9(3) C5 C6 H6A 120.5 C1 C6 H6A 120.5 C1 C7 H7A 109.5 C1 C7 H7B 109.5 H7A C7 H7B 109.5 C1 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C3 C8 H8A 109.5 C3 C8 H8B 109.5 H8A C8 H8B 109.5 C3 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C2 1.900(4) N1 O1 1.214(4) N1 O2 1.217(4) N1 C5 1.460(5) C1 C6 1.389(6) C1 C2 1.390(5) C1 C7 1.512(5) C2 C3 1.394(5) C3 C4 1.379(5) C3 C8 1.506(5) C4 C5 1.382(5) C4 H4A 0.9300 C5 C6 1.388(5) C6 H6A 0.9300 C7 H7A 0.9600 C7 H7B 0.9600 C7 H7C 0.9600 C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag C4 H4A O1 2_665 0.93 2.51 3.377(5) 156 yes C6 H6A O2 2_575 0.93 2.55 3.351(5) 144 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C6 C1 C2 C3 0.2(5) C7 C1 C2 C3 -178.8(4) C6 C1 C2 Br1 -179.5(3) C7 C1 C2 Br1 1.6(5) C1 C2 C3 C4 1.0(5) Br1 C2 C3 C4 -179.4(3) C1 C2 C3 C8 -178.6(4) Br1 C2 C3 C8 1.1(5) C2 C3 C4 C5 -1.3(5) C8 C3 C4 C5 178.2(3) C3 C4 C5 C6 0.6(6) C3 C4 C5 N1 179.7(3) O1 N1 C5 C4 -12.0(5) O2 N1 C5 C4 167.5(4) O1 N1 C5 C6 167.1(4) O2 N1 C5 C6 -13.4(5) C4 C5 C6 C1 0.6(6) N1 C5 C6 C1 -178.5(3) C2 C1 C6 C5 -0.9(5) C7 C1 C6 C5 178.1(4) _cod_database_fobs_code 2241936