# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _publ_contact_author 'Alexander J. A. Cobb' _publ_contact_author_email a.j.a.cobb@reading.ac.uk loop_ _publ_author_name 'Alexander J. A. Cobb' 'Sundaram Rajkumar' 'Kenneth Shankland' G.Brown data_Crystal3A _database_code_depnum_ccdc_archive 'CCDC 837100' _audit_creation_date 2011-07-15 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_systematic ; (+)-Ethyl (2R,4S-dinitro-3R-phenyl-1S-cyclohexyl) acetate ; _chemical_formula_moiety 'C16 H20 N2 O6' _chemical_formula_sum 'C16 H20 N2 O6' _chemical_formula_weight 336.34 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C16 H20 N2 O6' 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 7.95486(5) _cell_length_b 10.00542(6) _cell_length_c 20.80472(17) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1655.88(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 36335 _cell_measurement_theta_min 4.2466 _cell_measurement_theta_max 72.0830 _exptl_crystal_preparation 'heptane / DCM' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.349 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.870 _exptl_absorpt_correction_T_min 0.89083 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_sigmaI/netI 0.0355 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_number 47145 _diffrn_reflns_theta_min 4.2466 _diffrn_reflns_theta_max 72.0830 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.3468 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -34.00 -9.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 21.0000 68.0000 25 #__ type_ start__ end____ width___ exp.time_ 2 omega -92.00 -1.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -21.0000 82.0000 91 #__ type_ start__ end____ width___ exp.time_ 3 omega 0.00 91.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 41.1029 21.0000 -82.0000 91 #__ type_ start__ end____ width___ exp.time_ 4 omega -105.00 -80.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -21.0000 82.0000 25 #__ type_ start__ end____ width___ exp.time_ 5 omega -105.00 -80.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -21.0000 110.0000 25 #__ type_ start__ end____ width___ exp.time_ 6 omega 26.00 90.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -21.0000 -97.0000 64 #__ type_ start__ end____ width___ exp.time_ 7 omega 69.00 158.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 21.0000 -82.0000 89 #__ type_ start__ end____ width___ exp.time_ 8 omega 40.00 65.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -21.0000 -68.0000 25 #__ type_ start__ end____ width___ exp.time_ 9 omega 65.00 101.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 21.0000 -110.0000 36 #__ type_ start__ end____ width___ exp.time_ 10 omega 29.00 141.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -77.0000 120.0000 112 #__ type_ start__ end____ width___ exp.time_ 11 omega 32.00 98.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -45.0000 -30.0000 66 #__ type_ start__ end____ width___ exp.time_ 12 omega 32.00 98.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -45.0000 120.0000 66 #__ type_ start__ end____ width___ exp.time_ 13 omega -117.00 -15.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -38.0000 0.0000 102 #__ type_ start__ end____ width___ exp.time_ 14 omega -50.00 35.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 38.0000 150.0000 85 #__ type_ start__ end____ width___ exp.time_ 15 omega -38.00 75.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 41.1029 -77.0000 -90.0000 113 #__ type_ start__ end____ width___ exp.time_ 16 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 -60.0000 112 #__ type_ start__ end____ width___ exp.time_ 17 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 -150.0000 112 #__ type_ start__ end____ width___ exp.time_ 18 omega 80.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 45.0000 150.0000 98 #__ type_ start__ end____ width___ exp.time_ 19 omega 29.00 141.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -77.0000 -30.0000 112 #__ type_ start__ end____ width___ exp.time_ 20 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 60.0000 104 #__ type_ start__ end____ width___ exp.time_ 21 omega 46.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 15.0000 30.0000 132 #__ type_ start__ end____ width___ exp.time_ 22 omega -120.00 -7.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -77.0000 -30.0000 113 #__ type_ start__ end____ width___ exp.time_ 23 omega -75.00 38.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 77.0000 -180.0000 113 #__ type_ start__ end____ width___ exp.time_ 24 omega 7.00 120.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 41.1029 77.0000 120.0000 113 #__ type_ start__ end____ width___ exp.time_ 25 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 30.0000 112 #__ type_ start__ end____ width___ exp.time_ 26 omega 29.00 141.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -77.0000 -120.0000 112 #__ type_ start__ end____ width___ exp.time_ 27 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 90.0000 104 #__ type_ start__ end____ width___ exp.time_ 28 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -30.0000 104 #__ type_ start__ end____ width___ exp.time_ 29 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -180.0000 104 #__ type_ start__ end____ width___ exp.time_ 30 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -90.0000 104 #__ type_ start__ end____ width___ exp.time_ 31 omega -50.00 35.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 38.0000 60.0000 85 #__ type_ start__ end____ width___ exp.time_ 32 omega -120.00 -7.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -77.0000 150.0000 113 #__ type_ start__ end____ width___ exp.time_ 33 omega -120.00 -7.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -77.0000 -120.0000 113 #__ type_ start__ end____ width___ exp.time_ 34 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 120.0000 112 #__ type_ start__ end____ width___ exp.time_ 35 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -120.0000 104 #__ type_ start__ end____ width___ exp.time_ 36 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 150.0000 104 #__ type_ start__ end____ width___ exp.time_ 37 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 30.0000 104 #__ type_ start__ end____ width___ exp.time_ 38 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -60.0000 104 #__ type_ start__ end____ width___ exp.time_ 39 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 0.0000 104 #__ type_ start__ end____ width___ exp.time_ 40 omega -75.00 38.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 77.0000 -150.0000 113 #__ type_ start__ end____ width___ exp.time_ 41 omega -120.00 -7.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -77.0000 60.0000 113 #__ type_ start__ end____ width___ exp.time_ 42 omega -38.00 75.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 41.1029 -77.0000 0.0000 113 #__ type_ start__ end____ width___ exp.time_ 43 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 150.0000 112 #__ type_ start__ end____ width___ exp.time_ 44 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 0.0000 112 #__ type_ start__ end____ width___ exp.time_ 45 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 -120.0000 112 #__ type_ start__ end____ width___ exp.time_ 46 omega -140.00 -28.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -77.0000 60.0000 112 #__ type_ start__ end____ width___ exp.time_ 47 omega 29.00 141.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 -77.0000 60.0000 112 #__ type_ start__ end____ width___ exp.time_ 48 omega 74.00 178.00 1.0000 12.0000 omega____ theta____ kappa____ phi______ frames - 107.2551 77.0000 -150.0000 104 #__ type_ start__ end____ width___ exp.time_ 49 omega -117.00 -15.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -41.1029 -38.0000 -180.0000 102 #__ type_ start__ end____ width___ exp.time_ 50 omega 7.00 120.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 41.1029 77.0000 30.0000 113 ; _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.1809384000 _diffrn_orient_matrix_UB_12 0.0359876000 _diffrn_orient_matrix_UB_13 0.0199745000 _diffrn_orient_matrix_UB_21 0.0507134000 _diffrn_orient_matrix_UB_22 0.1481730000 _diffrn_orient_matrix_UB_23 0.0055269000 _diffrn_orient_matrix_UB_31 -0.0467826000 _diffrn_orient_matrix_UB_32 0.0217353000 _diffrn_orient_matrix_UB_33 -0.0710710000 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_theta 66.49 _reflns_odcompleteness_iscentric 1 _reflns_number_total 3142 _reflns_number_gt 3111 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0323P)^2^+0.2258P] 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 0.0022(2) _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 -0.02(11) _refine_ls_number_reflns 3142 _refine_ls_number_parameters 326 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0214 _refine_ls_R_factor_gt 0.0211 _refine_ls_wR_factor_ref 0.0562 _refine_ls_wR_factor_gt 0.0559 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _refine_ls_shift/su_max 0.038 _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 O1 O 0.88186(9) 0.91324(7) 0.16343(3) 0.02267(16) Uani 1 1 d . . . O2 O 0.70230(9) 0.95654(7) 0.24394(3) 0.02593(16) Uani 1 1 d . . . N1 N 0.80226(11) 1.41633(8) 0.18725(4) 0.02488(19) Uani 1 1 d . . . O3 O 0.91051(10) 1.40558(8) 0.14565(4) 0.03524(19) Uani 1 1 d . . . O4 O 0.82684(10) 1.46571(8) 0.24013(4) 0.03402(19) Uani 1 1 d . . . C2 C 0.62893(12) 1.36108(9) 0.17420(4) 0.0203(2) Uani 1 1 d . A . C15 C 0.50014(13) 1.76452(10) 0.11028(5) 0.0243(2) Uani 1 1 d . . . C11 C 0.58771(13) 1.53770(10) 0.08916(5) 0.0226(2) Uani 1 1 d . A . C8 C 0.77562(12) 0.99052(9) 0.19567(5) 0.0201(2) Uani 1 1 d . . . C9 C 0.90784(13) 0.77890(10) 0.18860(5) 0.0237(2) Uani 1 1 d . . . C1 C 0.62424(13) 1.21253(9) 0.19449(5) 0.0214(2) Uani 1 1 d . . . C6 C 0.44628(14) 1.16129(10) 0.18006(5) 0.0264(2) Uani 1 1 d . A . C5 C 0.39397(17) 1.18324(11) 0.11004(6) 0.0339(3) Uani 1 1 d D . . C14 C 0.60407(14) 1.81072(11) 0.06175(5) 0.0274(2) Uani 1 1 d . . . C16 C 0.49116(13) 1.62868(10) 0.12384(5) 0.0219(2) Uani 1 1 d . . . C7 C 0.76254(13) 1.12645(10) 0.16428(5) 0.0240(2) Uani 1 1 d . . . C3 C 0.58023(14) 1.38901(10) 0.10426(5) 0.0240(2) Uani 1 1 d D . . C13 C 0.70012(16) 1.72095(12) 0.02714(6) 0.0335(3) Uani 1 1 d . A . C10 C 1.05546(15) 0.72150(11) 0.15353(6) 0.0321(3) Uani 1 1 d . . . C12 C 0.69287(16) 1.58527(12) 0.04091(5) 0.0318(2) Uani 1 1 d . . . C4 C 0.4039(5) 1.3316(4) 0.0929(4) 0.0307(4) Uani 0.50(2) 1 d PD A 1 H4 H 0.3195 1.3830 0.1186 0.037 Uiso 0.50(2) 1 calc PR A 1 N2 N 0.3730(13) 1.3532(10) 0.0216(3) 0.0291(13) Uani 0.50(2) 1 d PD A 1 O6 O 0.2348(9) 1.3977(11) 0.0094(4) 0.0553(15) Uani 0.50(2) 1 d PD A 1 O5 O 0.4775(14) 1.3261(10) -0.01926(18) 0.0503(17) Uani 0.50(2) 1 d PD A 1 C4A C 0.4010(5) 1.3338(4) 0.0974(4) 0.0307(4) Uani 0.50(2) 1 d PD A 2 H4A H 0.3271 1.3799 0.1294 0.037 Uiso 0.50(2) 1 calc PR A 2 N2A N 0.3286(15) 1.3559(11) 0.0306(4) 0.0363(15) Uani 0.50(2) 1 d PD A 2 O6A O 0.2075(12) 1.4279(8) 0.0228(5) 0.0518(17) Uani 0.50(2) 1 d PD A 2 O5A O 0.4004(19) 1.2947(6) -0.0119(3) 0.053(2) Uani 0.50(2) 1 d PD A 2 H6A H 0.3649(16) 1.2093(13) 0.2096(6) 0.028(3) Uiso 1 1 d . . . H6B H 0.4391(16) 1.0638(13) 0.1880(6) 0.027(3) Uiso 1 1 d . . . H1 H 0.6419(14) 1.2123(12) 0.2406(6) 0.023(3) Uiso 1 1 d . . . H3 H 0.6544(16) 1.3407(14) 0.0747(6) 0.031(3) Uiso 1 1 d . . . H9A H 0.8062(17) 0.7276(13) 0.1822(6) 0.028(3) Uiso 1 1 d . . . H5A H 0.279(2) 1.1506(16) 0.1047(7) 0.045(4) Uiso 1 1 d . . . H2 H 0.5560(15) 1.4110(11) 0.2027(5) 0.018(3) Uiso 1 1 d . . . H16 H 0.4173(16) 1.5975(12) 0.1569(6) 0.021(3) Uiso 1 1 d . . . H14 H 0.6115(16) 1.9052(14) 0.0525(6) 0.029(3) Uiso 1 1 d . . . H15 H 0.4357(18) 1.8271(14) 0.1351(6) 0.035(3) Uiso 1 1 d . . . H9B H 0.9261(16) 0.7857(12) 0.2353(6) 0.027(3) Uiso 1 1 d . . . H7A H 0.8735(18) 1.1696(14) 0.1683(6) 0.034(3) Uiso 1 1 d . . . H7B H 0.7465(18) 1.1132(15) 0.1200(7) 0.037(4) Uiso 1 1 d . . . H5B H 0.4727(18) 1.1327(15) 0.0782(7) 0.037(4) Uiso 1 1 d . . . H10A H 1.1499(17) 0.7777(15) 0.1628(7) 0.036(4) Uiso 1 1 d . . . H10B H 1.076(2) 0.6329(17) 0.1701(7) 0.045(4) Uiso 1 1 d . . . H13 H 0.769(2) 1.7488(17) -0.0054(8) 0.049(4) Uiso 1 1 d . . . H12 H 0.759(2) 1.5207(16) 0.0161(8) 0.050(4) Uiso 1 1 d . . . H10C H 1.0345(18) 0.7166(15) 0.1071(8) 0.038(4) Uiso 1 1 d . . . 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 O1 0.0244(3) 0.0177(3) 0.0259(3) 0.0026(3) 0.0030(3) 0.0030(3) O2 0.0296(4) 0.0220(3) 0.0261(4) 0.0060(3) 0.0063(3) 0.0030(3) N1 0.0292(4) 0.0155(4) 0.0300(4) 0.0031(3) -0.0024(4) 0.0032(3) O3 0.0321(4) 0.0305(4) 0.0432(4) 0.0031(3) 0.0086(4) -0.0008(3) O4 0.0387(4) 0.0285(4) 0.0349(4) -0.0051(3) -0.0117(3) 0.0028(3) C2 0.0241(5) 0.0175(4) 0.0194(5) -0.0010(4) 0.0003(4) 0.0022(4) C15 0.0214(5) 0.0213(5) 0.0302(5) -0.0018(4) -0.0027(4) 0.0001(4) C11 0.0293(5) 0.0204(5) 0.0181(4) 0.0010(4) -0.0024(4) 0.0031(4) C8 0.0208(4) 0.0192(4) 0.0205(5) 0.0002(4) -0.0010(4) 0.0002(4) C9 0.0219(5) 0.0171(4) 0.0320(5) 0.0031(4) -0.0012(4) 0.0013(4) C1 0.0275(5) 0.0180(5) 0.0186(5) 0.0025(4) 0.0016(4) 0.0024(4) C6 0.0291(5) 0.0192(5) 0.0307(6) 0.0019(4) -0.0002(4) 0.0001(4) C5 0.0427(7) 0.0194(5) 0.0396(6) -0.0012(5) -0.0159(5) -0.0005(5) C14 0.0261(5) 0.0220(5) 0.0341(5) 0.0070(4) -0.0058(4) -0.0019(4) C16 0.0219(5) 0.0220(5) 0.0218(5) 0.0007(4) 0.0008(4) -0.0003(4) C7 0.0307(5) 0.0189(5) 0.0225(5) 0.0034(4) 0.0051(4) 0.0028(4) C3 0.0353(5) 0.0184(5) 0.0182(5) -0.0012(4) -0.0005(4) 0.0051(4) C13 0.0349(6) 0.0362(6) 0.0293(6) 0.0122(5) 0.0076(5) 0.0017(5) C10 0.0276(5) 0.0247(5) 0.0441(7) -0.0002(5) 0.0037(5) 0.0044(4) C12 0.0402(6) 0.0317(6) 0.0234(5) 0.0047(4) 0.0086(5) 0.0096(5) C4 0.0440(6) 0.0205(5) 0.0274(10) -0.0010(5) -0.0154(6) 0.0024(5) N2 0.040(3) 0.0183(15) 0.029(2) -0.0010(18) -0.0170(17) 0.001(2) O6 0.036(2) 0.080(4) 0.050(3) 0.016(2) -0.0180(16) 0.018(2) O5 0.059(3) 0.067(3) 0.0244(11) -0.0075(12) -0.0045(14) 0.017(3) C4A 0.0440(6) 0.0205(5) 0.0274(10) -0.0010(5) -0.0154(6) 0.0024(5) N2A 0.048(4) 0.0231(17) 0.038(2) 0.0021(15) -0.014(2) -0.004(3) O6A 0.050(3) 0.043(2) 0.062(4) 0.023(2) -0.024(2) 0.0003(18) O5A 0.080(5) 0.0543(18) 0.0253(14) -0.0074(12) -0.015(2) 0.008(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_publ_flag O1 C8 1.3274(12) no O1 C9 1.4573(12) no O2 C8 1.2101(12) no O3 N1 1.2256(12) no O4 N1 1.2218(12) no O5 N2 1.220(12) no O6 N2 1.213(13) no N1 C2 1.5101(13) no N2 C4 1.519(10) no C1 C2 1.5455(13) no C1 C6 1.5353(15) no C1 C7 1.5320(14) no C2 C3 1.5315(13) no C3 C4 1.534(4) no C3 C11 1.5217(14) no C4 C5 1.529(4) no C5 C6 1.5309(16) no C7 C8 1.5123(14) no C9 C10 1.4971(16) no C11 C12 1.3907(15) no C11 C16 1.3925(14) no C12 C13 1.3886(17) no C13 C14 1.3817(16) no C14 C15 1.3844(15) no C15 C16 1.3899(14) no C1 H1 0.970(13) no C2 H2 0.968(11) no C3 H3 0.980(13) no C4 H4 1.000 no C5 H5A 0.978(16) no C5 H5B 1.043(15) no C6 H6A 1.014(13) no C6 H6B 0.991(13) no C7 H7A 0.986(14) no C7 H7B 0.939(15) no C9 H9A 0.967(13) no C9 H9B 0.985(13) no C10 H10A 0.958(14) no C10 H10B 0.965(17) no C10 H10C 0.982(17) no C12 H12 0.980(16) no C13 H13 0.914(17) no C14 H14 0.967(14) no C15 H15 0.960(14) no C16 H16 0.957(13) no O5A N2A 1.218(13) no O6A N2A 1.214(15) no N2A C4A 1.521(12) no C3 C4A 1.536(4) no C4A C5 1.530(4) no C4A H4A 1.000 no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C8 O1 C9 116.49(7) no O3 N1 O4 123.98(9) no O3 N1 C2 118.84(8) no O4 N1 C2 117.13(8) no O5 N2 O6 123.6(8) no O5 N2 C4 122.6(8) no O6 N2 C4 113.8(7) no C2 C1 C6 106.86(8) no C2 C1 C7 114.28(8) no C6 C1 C7 113.22(8) no N1 C2 C1 108.96(7) no N1 C2 C3 109.57(8) no C1 C2 C3 115.40(8) no C2 C3 C4 108.0(3) no C2 C3 C11 111.39(8) no C4 C3 C11 111.72(19) no N2 C4 C3 104.2(5) no N2 C4 C5 111.0(5) no C3 C4 C5 112.0(3) no C4 C5 C6 110.3(3) no C1 C6 C5 112.88(9) no C1 C7 C8 112.20(8) no O1 C8 O2 124.23(9) no O1 C8 C7 110.45(8) no O2 C8 C7 125.30(9) no O1 C9 C10 106.86(8) no C3 C11 C12 120.47(9) no C3 C11 C16 120.70(9) no C12 C11 C16 118.82(10) no C11 C12 C13 120.56(11) no C12 C13 C14 120.33(11) no C13 C14 C15 119.56(10) no C14 C15 C16 120.35(10) no C11 C16 C15 120.38(10) no C2 C1 H1 105.6(7) no C6 C1 H1 109.0(7) no C7 C1 H1 107.5(7) no N1 C2 H2 104.4(7) no C1 C2 H2 108.3(6) no C3 C2 H2 109.6(6) no C2 C3 H3 110.7(8) no C4 C3 H3 105.6(8) no C11 C3 H3 109.2(8) no N2 C4 H4 110.0 no C3 C4 H4 110.0 no C5 C4 H4 110.0 no C4 C5 H5A 110.3(10) no C4 C5 H5B 107.0(9) no C6 C5 H5A 108.3(9) no C6 C5 H5B 111.8(8) no H5A C5 H5B 109.1(12) no C1 C6 H6A 108.2(7) no C1 C6 H6B 110.4(7) no C5 C6 H6A 109.6(7) no C5 C6 H6B 106.5(7) no H6A C6 H6B 109.2(10) no C1 C7 H7A 111.2(8) no C1 C7 H7B 112.6(9) no C8 C7 H7A 107.2(8) no C8 C7 H7B 107.8(9) no H7A C7 H7B 105.5(11) no O1 C9 H9A 108.8(8) no O1 C9 H9B 108.2(7) no C10 C9 H9A 112.7(8) no C10 C9 H9B 113.1(7) no H9A C9 H9B 107.2(10) no C9 C10 H10A 107.0(9) no C9 C10 H10B 108.1(9) no C9 C10 H10C 111.4(9) no H10A C10 H10B 109.5(13) no H10A C10 H10C 111.1(12) no H10B C10 H10C 109.5(13) no C11 C12 H12 118.5(10) no C13 C12 H12 120.9(10) no C12 C13 H13 118.4(11) no C14 C13 H13 121.3(11) no C13 C14 H14 119.9(8) no C15 C14 H14 120.6(8) no C14 C15 H15 119.6(8) no C16 C15 H15 120.1(8) no C11 C16 H16 119.9(7) no C15 C16 H16 119.8(7) no O5A N2A O6A 125.0(10) no O5A N2A C4A 114.4(10) no O6A N2A C4A 120.6(9) no N2A C4A C3 112.6(6) no N2A C4A C5 106.6(6) no N2A C4A H4A 109.0 no C2 C3 C4A 104.9(3) no C4A C3 C11 111.64(18) no C4A C3 H3 108.9(8) no C4A C5 C6 107.2(3) no C4A C5 H5A 110.1(10) no C4A C5 H5B 110.3(9) no C3 C4A H4A 109.0 no C5 C4A H4A 109.0 no 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 _geom_torsion_publ_flag C9 O1 C8 O2 0.69(14) no C9 O1 C8 C7 179.60(8) no C8 O1 C9 C10 -168.65(8) no O3 N1 C2 C1 87.83(10) no O3 N1 C2 C3 -39.29(11) no O4 N1 C2 C1 -89.91(10) no O4 N1 C2 C3 142.98(8) no O5 N2 C4 C3 46.3(11) no O5 N2 C4 C5 -74.5(11) no O6 N2 C4 C3 -134.8(8) no O6 N2 C4 C5 104.5(9) no C6 C1 C2 N1 -179.80(7) no C6 C1 C2 C3 -56.08(11) no C7 C1 C2 N1 -53.75(10) no C7 C1 C2 C3 69.98(11) no C2 C1 C6 C5 55.13(11) no C7 C1 C6 C5 -71.56(11) no C2 C1 C7 C8 168.08(8) no C6 C1 C7 C8 -69.26(11) no N1 C2 C3 C4 -179.98(19) no N1 C2 C3 C11 -56.94(10) no C1 C2 C3 C4 56.6(2) no C1 C2 C3 C11 179.66(8) no C2 C3 C4 N2 -175.3(4) no C2 C3 C4 C5 -55.3(5) no C11 C3 C4 N2 61.8(5) no C11 C3 C4 C5 -178.2(3) no C2 C3 C11 C12 120.82(11) no C2 C3 C11 C16 -58.39(13) no C4 C3 C11 C12 -118.3(3) no C4 C3 C11 C16 62.5(3) no N2 C4 C5 C6 173.1(5) no C3 C4 C5 C6 57.2(5) no C4 C5 C6 C1 -57.7(2) no C1 C7 C8 O1 172.42(8) no C1 C7 C8 O2 -8.67(14) no C3 C11 C12 C13 -179.88(10) no C16 C11 C12 C13 -0.65(17) no C3 C11 C16 C15 179.24(10) no C12 C11 C16 C15 0.00(16) no C11 C12 C13 C14 0.70(18) no C12 C13 C14 C15 -0.09(17) no C13 C14 C15 C16 -0.54(16) no C14 C15 C16 C11 0.58(16) no O6A N2A C4A C3 -115.3(10) no O6A N2A C4A C5 121.6(10) no O5A N2A C4A C3 65.7(11) no O5A N2A C4A C5 -57.3(11) no C2 C3 C4A N2A 178.5(5) no C11 C3 C4A N2A 57.8(6) no N2A C4A C5 C6 -173.2(5) no C4A C3 C11 C12 -122.3(3) no C4A C3 C11 C16 58.5(3) no N1 C2 C3 C4A -177.89(18) no C1 C2 C3 C4A 58.7(2) no C4A C5 C6 C1 -59.8(2) no _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 70.08 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.191 _refine_diff_density_min -0.119 _refine_diff_density_rms 0.024 data_Crystal13 _database_code_depnum_ccdc_archive 'CCDC 837219' _audit_creation_method SHELXL-97 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _chemical_name_systematic ; 'Ethyl 2(R)-[3(R)-(4'-methoxy-phenyl)-2(R),4(S)-dinitro-1(R)cyclohexyl] propanoate' ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H24 N2 O7' _chemical_formula_weight 380.39 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' _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_cell_setting orthorhombic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 5.5811(5) _cell_length_b 12.5943(15) _cell_length_c 26.723(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1878.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 797 _cell_measurement_theta_min 3.3049 _cell_measurement_theta_max 62.8276 _exptl_crystal_preparation 'heptane / DCM' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.875 _exptl_absorpt_correction_T_min 0.40184 _exptl_absorpt_correction_T_max 1.00000 _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. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Gemini ultra' _diffrn_detector_area_resol_mean 16.2086 _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4528 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_sigmaI/netI 0.0924 _diffrn_reflns_limit_h_min -3 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 62.92 _reflns_number_total 2674 _reflns_number_gt 1667 _reflns_threshold_expression >2\s(I) _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0496P)^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 constr _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 0.2(4) _chemical_absolute_configuration syn _refine_ls_number_reflns 2674 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0992 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1169 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_restrained_S_all 0.919 _refine_ls_shift/su_max 0.001 _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 O7 O 0.7632(5) 0.3991(2) 0.03407(10) 0.0364(8) Uani 1 1 d . . . O3 O 0.9016(6) 0.2487(2) 0.24652(12) 0.0418(9) Uani 1 1 d . . . O2 O 0.4414(6) 0.1013(3) 0.31397(11) 0.0434(9) Uani 1 1 d . . . O6 O 0.7127(6) -0.0976(3) 0.08590(11) 0.0475(9) Uani 1 1 d . . . O1 O 0.6448(6) 0.0797(3) 0.38528(10) 0.0411(8) Uani 1 1 d . . . O4 O 1.1562(5) 0.1403(3) 0.21279(11) 0.0384(8) Uani 1 1 d . . . N1 N 0.9522(7) 0.1639(3) 0.22665(13) 0.0298(9) Uani 1 1 d . . . O5 O 0.3282(6) -0.0875(3) 0.09141(12) 0.0526(10) Uani 1 1 d . . . C4 C 0.5494(8) -0.0325(3) 0.16062(14) 0.0299(10) Uani 1 1 d . . . H4 H 0.3979 0.0056 0.1694 0.045 Uiso 1 1 calc R . . C2 C 0.7586(7) 0.0824(3) 0.22017(15) 0.0280(10) Uani 1 1 d . . . H2 H 0.6002 0.1161 0.2276 0.042 Uiso 1 1 calc R . . C3 C 0.7606(8) 0.0450(3) 0.16517(14) 0.0270(10) Uani 1 1 d . . . H3 H 0.9119 0.0044 0.1594 0.041 Uiso 1 1 calc R . . N2 N 0.5294(7) -0.0749(3) 0.10800(14) 0.0372(10) Uani 1 1 d . . . C14 C 0.7699(8) 0.3095(3) 0.06268(15) 0.0269(10) Uani 1 1 d . . . C13 C 0.9456(8) 0.2327(3) 0.06073(16) 0.0305(11) Uani 1 1 d . . . H13 H 1.0720 0.2386 0.0371 0.046 Uiso 1 1 calc R . . C7 C 0.8412(8) 0.0256(4) 0.31146(15) 0.0315(11) Uani 1 1 d . . . H7 H 0.9624 0.0840 0.3104 0.047 Uiso 1 1 calc R . . C11 C 0.7521(7) 0.1359(3) 0.12786(14) 0.0258(10) Uani 1 1 d . . . C15 C 0.5795(7) 0.2977(3) 0.09586(15) 0.0291(10) Uani 1 1 d . . . H15 H 0.4533 0.3483 0.0962 0.044 Uiso 1 1 calc R . . C1 C 0.7988(8) -0.0098(3) 0.25683(15) 0.0290(11) Uani 1 1 d . . . H1 H 0.9492 -0.0461 0.2458 0.043 Uiso 1 1 calc R . . C8 C 0.6172(8) 0.0711(4) 0.33575(16) 0.0325(11) Uani 1 1 d . . . C16 C 0.5737(7) 0.2126(3) 0.12824(15) 0.0283(11) Uani 1 1 d . . . H16 H 0.4450 0.2064 0.1513 0.042 Uiso 1 1 calc R . . C6 C 0.5982(8) -0.0896(3) 0.24975(16) 0.0346(11) Uani 1 1 d . . . H6A H 0.4443 -0.0566 0.2597 0.052 Uiso 1 1 calc R . . H6B H 0.6264 -0.1514 0.2719 0.052 Uiso 1 1 calc R . . C12 C 0.9382(7) 0.1471(4) 0.09317(15) 0.0301(10) Uani 1 1 d . . . H12 H 1.0614 0.0952 0.0919 0.045 Uiso 1 1 calc R . . C5 C 0.5804(9) -0.1277(3) 0.19568(16) 0.0363(12) Uani 1 1 d . . . H5A H 0.4420 -0.1763 0.1921 0.054 Uiso 1 1 calc R . . H5B H 0.7274 -0.1672 0.1866 0.054 Uiso 1 1 calc R . . C18 C 0.9521(8) -0.0650(3) 0.34167(16) 0.0387(12) Uani 1 1 d . . . H18A H 0.9852 -0.0405 0.3758 0.058 Uiso 1 1 calc R . . H18B H 1.1019 -0.0876 0.3258 0.058 Uiso 1 1 calc R . . H18C H 0.8402 -0.1249 0.3428 0.058 Uiso 1 1 calc R . . C9 C 0.4478(9) 0.1283(4) 0.41269(16) 0.0479(13) Uani 1 1 d . . . H9A H 0.3039 0.0825 0.4108 0.072 Uiso 1 1 calc R . . H9B H 0.4079 0.1981 0.3979 0.072 Uiso 1 1 calc R . . C17 C 0.9708(9) 0.4239(4) 0.00498(17) 0.0439(13) Uani 1 1 d . . . H17A H 1.1129 0.4227 0.0265 0.066 Uiso 1 1 calc R . . H17B H 0.9527 0.4947 -0.0097 0.066 Uiso 1 1 calc R . . H17C H 0.9890 0.3713 -0.0218 0.066 Uiso 1 1 calc R . . C10 C 0.5238(11) 0.1417(5) 0.46600(17) 0.0627(17) Uani 1 1 d . . . H10A H 0.5644 0.0722 0.4802 0.094 Uiso 1 1 calc R . . H10B H 0.3925 0.1734 0.4852 0.094 Uiso 1 1 calc R . . H10C H 0.6643 0.1882 0.4675 0.094 Uiso 1 1 calc R . . 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 O7 0.0430(19) 0.0324(17) 0.0339(15) 0.0077(16) 0.0075(17) 0.0043(18) O3 0.0417(19) 0.0302(17) 0.053(2) -0.0049(17) 0.0055(19) -0.0017(18) O2 0.0365(18) 0.054(2) 0.0399(18) 0.0029(18) 0.0027(18) 0.013(2) O6 0.045(2) 0.050(2) 0.0475(19) -0.0102(19) 0.0091(19) 0.001(2) O1 0.0395(17) 0.049(2) 0.0346(17) -0.0070(17) 0.0011(16) 0.0078(18) O4 0.0229(16) 0.048(2) 0.0443(19) -0.0014(17) -0.0001(17) 0.0030(17) N1 0.027(2) 0.029(2) 0.033(2) 0.0032(19) 0.002(2) 0.003(2) O5 0.0431(19) 0.061(2) 0.054(2) -0.007(2) -0.0185(19) -0.010(2) C4 0.029(2) 0.033(2) 0.028(2) -0.003(2) 0.001(2) -0.003(2) C2 0.021(2) 0.028(2) 0.035(2) 0.000(2) 0.004(2) -0.003(2) C3 0.023(2) 0.027(2) 0.031(2) 0.004(2) 0.001(2) 0.001(2) N2 0.042(2) 0.031(2) 0.038(2) -0.002(2) 0.001(2) -0.003(2) C14 0.028(2) 0.027(2) 0.026(2) 0.001(2) -0.002(2) -0.004(2) C13 0.025(2) 0.035(3) 0.032(2) 0.000(2) 0.003(2) -0.003(3) C7 0.026(2) 0.033(2) 0.035(2) 0.005(2) 0.002(2) -0.001(2) C11 0.023(2) 0.027(2) 0.027(2) -0.002(2) 0.000(2) -0.002(2) C15 0.025(2) 0.028(2) 0.034(2) 0.003(2) -0.002(2) 0.002(2) C1 0.026(2) 0.030(2) 0.031(2) 0.002(2) 0.004(2) 0.003(2) C8 0.031(3) 0.032(3) 0.034(3) 0.003(2) 0.002(2) 0.001(2) C16 0.019(2) 0.031(2) 0.035(3) -0.002(2) 0.000(2) -0.002(2) C6 0.035(3) 0.030(2) 0.039(2) 0.006(2) -0.002(2) -0.003(2) C12 0.019(2) 0.038(3) 0.033(2) 0.001(2) -0.001(2) 0.004(2) C5 0.039(3) 0.033(3) 0.038(3) 0.006(2) -0.004(3) -0.006(3) C18 0.035(3) 0.042(3) 0.039(3) 0.004(2) 0.000(2) 0.005(3) C9 0.060(3) 0.043(3) 0.041(3) -0.003(2) 0.013(3) 0.010(3) C17 0.052(3) 0.037(3) 0.043(3) 0.011(2) 0.012(3) -0.006(3) C10 0.069(4) 0.071(4) 0.048(3) -0.020(3) 0.005(3) -0.004(4) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O7 C14 1.364(5) . ? O7 C17 1.430(5) . ? O3 N1 1.225(4) . ? O2 C8 1.202(5) . ? O6 N2 1.215(4) . ? O1 C8 1.337(5) . ? O1 C9 1.455(5) . ? O4 N1 1.234(4) . ? N1 C2 1.500(5) . ? O5 N2 1.218(5) . ? C4 N2 1.508(5) . ? C4 C5 1.532(6) . ? C4 C3 1.535(6) . ? C4 H4 1.0000 . ? C2 C1 1.536(5) . ? C2 C3 1.543(5) . ? C2 H2 1.0000 . ? C3 C11 1.518(6) . ? C3 H3 1.0000 . ? C14 C13 1.378(6) . ? C14 C15 1.392(5) . ? C13 C12 1.384(6) . ? C13 H13 0.9500 . ? C7 C8 1.521(6) . ? C7 C18 1.528(6) . ? C7 C1 1.545(6) . ? C7 H7 1.0000 . ? C11 C16 1.388(5) . ? C11 C12 1.399(5) . ? C15 C16 1.377(6) . ? C15 H15 0.9500 . ? C1 C6 1.516(6) . ? C1 H1 1.0000 . ? C16 H16 0.9500 . ? C6 C5 1.526(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C12 H12 0.9500 . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C9 C10 1.496(6) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? 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 C14 O7 C17 117.6(4) . . ? C8 O1 C9 116.4(4) . . ? O3 N1 O4 123.6(4) . . ? O3 N1 C2 118.7(4) . . ? O4 N1 C2 117.7(4) . . ? N2 C4 C5 107.5(3) . . ? N2 C4 C3 110.9(4) . . ? C5 C4 C3 111.3(4) . . ? N2 C4 H4 109.0 . . ? C5 C4 H4 109.0 . . ? C3 C4 H4 109.0 . . ? N1 C2 C1 109.8(3) . . ? N1 C2 C3 108.3(3) . . ? C1 C2 C3 112.1(3) . . ? N1 C2 H2 108.9 . . ? C1 C2 H2 108.9 . . ? C3 C2 H2 108.9 . . ? C11 C3 C4 113.8(4) . . ? C11 C3 C2 113.3(3) . . ? C4 C3 C2 105.3(3) . . ? C11 C3 H3 108.1 . . ? C4 C3 H3 108.1 . . ? C2 C3 H3 108.1 . . ? O6 N2 O5 124.6(4) . . ? O6 N2 C4 118.3(4) . . ? O5 N2 C4 117.0(4) . . ? O7 C14 C13 125.4(4) . . ? O7 C14 C15 115.1(4) . . ? C13 C14 C15 119.5(4) . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C8 C7 C18 112.9(4) . . ? C8 C7 C1 112.7(4) . . ? C18 C7 C1 110.2(4) . . ? C8 C7 H7 106.9 . . ? C18 C7 H7 106.9 . . ? C1 C7 H7 106.9 . . ? C16 C11 C12 117.8(4) . . ? C16 C11 C3 122.8(4) . . ? C12 C11 C3 119.2(4) . . ? C16 C15 C14 120.1(4) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C6 C1 C2 108.3(3) . . ? C6 C1 C7 115.0(4) . . ? C2 C1 C7 114.0(4) . . ? C6 C1 H1 106.3 . . ? C2 C1 H1 106.3 . . ? C7 C1 H1 106.3 . . ? O2 C8 O1 123.2(4) . . ? O2 C8 C7 125.7(4) . . ? O1 C8 C7 111.0(4) . . ? C15 C16 C11 121.3(4) . . ? C15 C16 H16 119.3 . . ? C11 C16 H16 119.3 . . ? C1 C6 C5 112.0(4) . . ? C1 C6 H6A 109.2 . . ? C5 C6 H6A 109.2 . . ? C1 C6 H6B 109.2 . . ? C5 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C13 C12 C11 121.1(4) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C6 C5 C4 109.9(4) . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5B 109.7 . . ? C4 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C7 C18 H18A 109.5 . . ? C7 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C7 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O1 C9 C10 108.2(4) . . ? O1 C9 H9A 110.1 . . ? C10 C9 H9A 110.1 . . ? O1 C9 H9B 110.1 . . ? C10 C9 H9B 110.1 . . ? H9A C9 H9B 108.4 . . ? O7 C17 H17A 109.5 . . ? O7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 62.92 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.255 _refine_diff_density_min -0.302 _refine_diff_density_rms 0.055 data_Crystal_3i _database_code_depnum_ccdc_archive 'CCDC 837234' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ethyl 2-[(1S,2R,3R,4S)-2-methyl-2,4-dinitro-3- phenylcyclohexyl]acetate ; _chemical_formula_moiety 'C17 H22 N2 O6' _chemical_formula_sum 'C17 H22 N2 O6' _chemical_formula_weight 350.37 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.1928(5) _cell_length_b 6.6518(4) _cell_length_c 12.7044(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.098(5) _cell_angle_gamma 90.00 _cell_volume 860.11(8) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3023 _cell_measurement_theta_min 2.4920 _cell_measurement_theta_max 28.9050 _exptl_crystal_preparation 'heptane / DCM' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_T_min 0.70238 _exptl_absorpt_correction_T_max 1.00000 _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. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 Gemini _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10366 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0646 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.50 _diffrn_reflns_theta_max 28.97 _reflns_number_total 3903 _reflns_number_gt 2996 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0694P)^2^+0.0784P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _chemical_absolute_configuration syn _refine_ls_number_reflns 3903 _refine_ls_number_parameters 228 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0831 _refine_ls_R_factor_gt 0.0608 _refine_ls_wR_factor_ref 0.1457 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _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 O6 O -0.8149(2) -0.4486(4) -0.02016(18) 0.0431(6) Uani 1 1 d . . . O4 O -0.8583(2) 0.2855(3) -0.27308(17) 0.0366(5) Uani 1 1 d . . . O5 O -0.9435(2) -0.2085(4) 0.02043(16) 0.0463(6) Uani 1 1 d . . . N1 N -0.8814(2) 0.1604(4) -0.3432(2) 0.0285(6) Uani 1 1 d . . . O1 O -1.3209(2) 0.3371(4) -0.3399(2) 0.0448(6) Uani 1 1 d . . . O3 O -0.8835(3) 0.2005(4) -0.43637(18) 0.0462(6) Uani 1 1 d . . . O2 O -1.3230(2) 0.0363(4) -0.4176(2) 0.0511(7) Uani 1 1 d . . . C3 C -0.8752(3) -0.0877(4) -0.1942(2) 0.0212(5) Uani 1 1 d . . . H3 H -0.9149 0.0188 -0.1532 0.025 Uiso 1 1 calc R . . N2 N -0.8942(2) -0.3180(4) -0.04386(19) 0.0286(6) Uani 1 1 d . . . C1 C -1.0715(3) -0.0608(4) -0.3326(2) 0.0241(6) Uani 1 1 d . . . H1 H -1.0887 -0.0611 -0.4092 0.029 Uiso 1 1 calc R . . C4 C -0.9338(3) -0.2889(4) -0.1600(2) 0.0232(6) Uani 1 1 d . . . H4 H -0.8961 -0.3978 -0.2006 0.028 Uiso 1 1 calc R . . C11 C -0.7270(3) -0.0793(4) -0.1702(2) 0.0253(6) Uani 1 1 d . . . C6 C -1.1220(3) -0.2620(4) -0.2916(2) 0.0272(6) Uani 1 1 d . . . H6A H -1.2170 -0.2651 -0.3014 0.033 Uiso 1 1 calc R . . H6B H -1.0873 -0.3705 -0.3330 0.033 Uiso 1 1 calc R . . C5 C -1.0829(3) -0.2971(5) -0.1751(2) 0.0280(6) Uani 1 1 d . . . H5A H -1.1219 -0.1946 -0.1324 0.034 Uiso 1 1 calc R . . H5B H -1.1145 -0.4273 -0.1532 0.034 Uiso 1 1 calc R . . C2 C -0.9193(3) -0.0536(4) -0.3121(2) 0.0221(6) Uani 1 1 d . . . C7 C -1.1474(3) 0.1172(4) -0.2895(2) 0.0287(7) Uani 1 1 d . . . H7A H -1.1681 0.0902 -0.2172 0.034 Uiso 1 1 calc R . . H7B H -1.0933 0.2371 -0.2899 0.034 Uiso 1 1 calc R . . C12 C -0.6724(3) 0.0824(6) -0.1155(2) 0.0350(7) Uani 1 1 d . . . H12 H -0.7263 0.1847 -0.0927 0.042 Uiso 1 1 calc R . . C16 C -0.6440(3) -0.2339(5) -0.2002(2) 0.0313(7) Uani 1 1 d . . . H16 H -0.6794 -0.3462 -0.2349 0.038 Uiso 1 1 calc R . . C13 C -0.5358(3) 0.0934(6) -0.0940(3) 0.0453(9) Uani 1 1 d . . . H13 H -0.4993 0.2031 -0.0577 0.054 Uiso 1 1 calc R . . C9 C -1.4396(3) 0.3958(6) -0.4054(3) 0.0443(9) Uani 1 1 d . . . H9A H -1.4312 0.3507 -0.4774 0.053 Uiso 1 1 calc R . . H9B H -1.4481 0.5410 -0.4061 0.053 Uiso 1 1 calc R . . C17 C -0.8536(3) -0.1929(5) -0.3896(2) 0.0295(6) Uani 1 1 d . . . H17A H -0.7611 -0.1650 -0.3882 0.044 Uiso 1 1 calc R . . H17B H -0.8915 -0.1708 -0.4595 0.044 Uiso 1 1 calc R . . H17C H -0.8670 -0.3303 -0.3697 0.044 Uiso 1 1 calc R . . C8 C -1.2731(3) 0.1521(5) -0.3559(3) 0.0340(7) Uani 1 1 d . . . C15 C -0.5096(3) -0.2216(6) -0.1790(2) 0.0419(8) Uani 1 1 d . . . H15 H -0.4554 -0.3247 -0.2003 0.050 Uiso 1 1 calc R . . C10 C -1.5591(3) 0.3042(7) -0.3622(3) 0.0514(9) Uani 1 1 d . . . H10A H -1.5629 0.3393 -0.2891 0.077 Uiso 1 1 calc R . . H10B H -1.5551 0.1606 -0.3690 0.077 Uiso 1 1 calc R . . H10C H -1.6361 0.3538 -0.4006 0.077 Uiso 1 1 calc R . . C14 C -0.4563(3) -0.0594(6) -0.1271(3) 0.0456(9) Uani 1 1 d . . . H14 H -0.3658 -0.0516 -0.1140 0.055 Uiso 1 1 calc R . . 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 O6 0.0338(12) 0.0479(15) 0.0468(13) 0.0171(11) -0.0043(9) 0.0125(11) O4 0.0427(13) 0.0231(11) 0.0439(12) -0.0012(11) 0.0022(9) -0.0022(10) O5 0.0623(16) 0.0475(15) 0.0287(11) -0.0049(11) -0.0025(10) 0.0124(14) N1 0.0250(13) 0.0252(15) 0.0351(14) 0.0049(11) -0.0012(10) 0.0025(11) O1 0.0316(12) 0.0356(14) 0.0659(16) -0.0053(11) -0.0094(11) 0.0059(10) O3 0.0551(15) 0.0474(15) 0.0350(12) 0.0169(11) -0.0064(10) -0.0118(12) O2 0.0362(13) 0.0544(17) 0.0602(16) -0.0219(13) -0.0200(11) 0.0106(12) C3 0.0217(13) 0.0187(14) 0.0232(12) 0.0006(11) 0.0015(10) 0.0012(11) N2 0.0260(12) 0.0277(14) 0.0319(12) 0.0056(11) -0.0011(10) -0.0043(11) C1 0.0198(13) 0.0249(16) 0.0268(13) -0.0003(12) -0.0057(10) 0.0005(11) C4 0.0266(14) 0.0211(16) 0.0218(12) -0.0003(11) -0.0005(10) 0.0002(11) C11 0.0240(14) 0.0288(16) 0.0228(13) 0.0027(12) -0.0018(10) -0.0054(12) C6 0.0241(14) 0.0250(17) 0.0317(14) -0.0022(12) -0.0042(11) -0.0018(11) C5 0.0246(14) 0.0256(16) 0.0333(14) 0.0032(13) -0.0022(11) -0.0035(12) C2 0.0217(13) 0.0201(15) 0.0240(13) -0.0005(11) -0.0031(10) 0.0016(11) C7 0.0229(14) 0.0273(17) 0.0354(16) -0.0045(13) -0.0025(11) 0.0039(12) C12 0.0369(17) 0.0406(19) 0.0272(15) -0.0020(14) -0.0018(12) -0.0091(15) C16 0.0225(14) 0.0372(18) 0.0339(15) -0.0027(14) -0.0022(11) 0.0021(13) C13 0.044(2) 0.057(2) 0.0338(17) -0.0018(17) -0.0063(14) -0.0272(18) C9 0.0376(19) 0.047(2) 0.0472(19) 0.0098(17) -0.0042(14) 0.0053(16) C17 0.0323(16) 0.0321(17) 0.0240(13) -0.0014(13) 0.0006(11) 0.0049(13) C8 0.0268(15) 0.0331(19) 0.0417(17) -0.0028(15) -0.0013(13) 0.0074(14) C15 0.0262(16) 0.064(2) 0.0352(16) 0.0060(18) 0.0006(13) 0.0058(17) C10 0.039(2) 0.064(3) 0.052(2) 0.009(2) 0.0076(16) 0.0080(19) C14 0.0243(16) 0.074(3) 0.0384(17) -0.0005(18) 0.0002(13) -0.0106(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O6 N2 1.213(3) . ? O4 N1 1.232(3) . ? O5 N2 1.222(3) . ? N1 O3 1.212(3) . ? N1 C2 1.532(4) . ? O1 C8 1.343(4) . ? O1 C9 1.484(4) . ? O2 C8 1.192(4) . ? C3 C11 1.526(4) . ? C3 C4 1.538(4) . ? C3 C2 1.556(4) . ? N2 C4 1.521(3) . ? C1 C7 1.532(4) . ? C1 C6 1.535(4) . ? C1 C2 1.560(4) . ? C4 C5 1.522(4) . ? C11 C12 1.382(4) . ? C11 C16 1.398(4) . ? C6 C5 1.530(4) . ? C2 C17 1.533(4) . ? C7 C8 1.514(4) . ? C12 C13 1.406(5) . ? C16 C15 1.384(4) . ? C13 C14 1.380(5) . ? C9 C10 1.493(5) . ? C15 C14 1.362(6) . ? 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 O3 N1 O4 123.4(3) . . ? O3 N1 C2 117.7(2) . . ? O4 N1 C2 118.8(2) . . ? C8 O1 C9 116.6(3) . . ? C11 C3 C4 111.8(2) . . ? C11 C3 C2 114.7(2) . . ? C4 C3 C2 107.6(2) . . ? O6 N2 O5 123.6(2) . . ? O6 N2 C4 118.1(2) . . ? O5 N2 C4 118.3(2) . . ? C7 C1 C6 111.6(2) . . ? C7 C1 C2 115.7(2) . . ? C6 C1 C2 108.6(2) . . ? N2 C4 C5 109.2(2) . . ? N2 C4 C3 107.4(2) . . ? C5 C4 C3 113.3(2) . . ? C12 C11 C16 118.4(3) . . ? C12 C11 C3 119.8(3) . . ? C16 C11 C3 121.7(2) . . ? C5 C6 C1 112.7(2) . . ? C4 C5 C6 108.9(2) . . ? N1 C2 C17 105.7(2) . . ? N1 C2 C3 108.7(2) . . ? C17 C2 C3 114.6(2) . . ? N1 C2 C1 104.3(2) . . ? C17 C2 C1 109.8(2) . . ? C3 C2 C1 112.9(2) . . ? C8 C7 C1 110.3(2) . . ? C11 C12 C13 120.4(3) . . ? C15 C16 C11 120.7(3) . . ? C14 C13 C12 119.6(3) . . ? O1 C9 C10 110.1(3) . . ? O2 C8 O1 123.1(3) . . ? O2 C8 C7 125.8(3) . . ? O1 C8 C7 111.0(3) . . ? C14 C15 C16 120.4(3) . . ? C15 C14 C13 120.3(3) . . ? _diffrn_measured_fraction_theta_max 0.906 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.455 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.052 data_Crystal_NoNumber _database_code_depnum_ccdc_archive 'CCDC 837235' _audit_creation_method SHELXL-97 _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET) (compiled Oct 25 2010,18:11:34) ; _chemical_name_systematic ; ethyl (2R)-2-[(1R,2R,3R,4S)-3-(4-methoxyphenyl)- 2,4-dinitrocyclohexyl]propanoate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O7' _chemical_formula_sum 'C18 H24 N2 O7' _chemical_formula_weight 380.39 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' _diffrn_measurement_method '\w scans' _symmetry_space_group_name_H-M 'P 1 21/c 1' _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.8847(13) _cell_length_b 5.6274(5) _cell_length_c 25.767(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.776(9) _cell_angle_gamma 90.00 _cell_volume 1866.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1566 _cell_measurement_theta_min 3.4314 _cell_measurement_theta_max 62.6103 _exptl_crystal_preparation 'heptane / DCM' _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max .41 _exptl_crystal_size_mid .39 _exptl_crystal_size_min .29 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.881 _exptl_absorpt_correction_T_min 0.76461 _exptl_absorpt_correction_T_max 1.00000 _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. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Gemini _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6452 _diffrn_reflns_av_R_equivalents 0.0458 _diffrn_reflns_av_sigmaI/netI 0.0492 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 62.70 _reflns_number_total 2990 _reflns_number_gt 2086 _reflns_threshold_expression >2\s(I) _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0611P)^2^+0.7098P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2990 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0793 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1433 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O4 O -1.07130(16) 0.2059(3) -0.33190(8) 0.0471(5) Uani 1 1 d . . . O7 O -1.40987(15) -0.1579(4) -0.17993(7) 0.0457(5) Uani 1 1 d . . . N1 N -1.04379(18) 0.0103(4) -0.31541(9) 0.0376(6) Uani 1 1 d . . . O5 O -1.36525(17) -0.2264(4) -0.42672(9) 0.0567(6) Uani 1 1 d . . . O6 O -1.36279(17) -0.6094(4) -0.42360(9) 0.0584(6) Uani 1 1 d . . . O2 O -0.85639(18) -0.0234(5) -0.46373(10) 0.0737(8) Uani 1 1 d . . . O3 O -0.9943(2) -0.0206(4) -0.27494(9) 0.0625(7) Uani 1 1 d . . . O1 O -0.72260(16) -0.1821(4) -0.41889(8) 0.0596(6) Uani 1 1 d . . . C16 C -1.3195(2) -0.0065(5) -0.30901(11) 0.0379(7) Uani 1 1 d . . . H16 H -1.3285 0.1116 -0.3352 0.046 Uiso 1 1 calc R . . N2 N -1.32124(19) -0.4143(5) -0.41766(9) 0.0423(6) Uani 1 1 d . . . C7 C -0.8843(2) -0.1901(5) -0.37976(11) 0.0404(7) Uani 1 1 d . . . H7 H -0.8752 -0.0581 -0.3539 0.049 Uiso 1 1 calc R . . C15 C -1.3753(2) 0.0118(5) -0.26437(11) 0.0394(7) Uani 1 1 d . . . H15 H -1.4220 0.1402 -0.2602 0.047 Uiso 1 1 calc R . . C3 C -1.1859(2) -0.1984(5) -0.36404(10) 0.0350(6) Uani 1 1 d . . . H3 H -1.2007 -0.0509 -0.3848 0.042 Uiso 1 1 calc R . . C13 C -1.2961(2) -0.3510(5) -0.23332(10) 0.0379(7) Uani 1 1 d . . . H13 H -1.2889 -0.4715 -0.2076 0.045 Uiso 1 1 calc R . . C2 C -1.0694(2) -0.2039(5) -0.34884(10) 0.0340(6) Uani 1 1 d . . . H2 H -1.0535 -0.3512 -0.3282 0.041 Uiso 1 1 calc R . . C4 C -1.2092(2) -0.4125(5) -0.39916(10) 0.0366(7) Uani 1 1 d . . . H4 H -1.1941 -0.5609 -0.3788 0.044 Uiso 1 1 calc R . . C12 C -1.2408(2) -0.3662(5) -0.27804(10) 0.0357(6) Uani 1 1 d . . . H12 H -1.1954 -0.4968 -0.2826 0.043 Uiso 1 1 calc R . . C8 C -0.8214(2) -0.1213(5) -0.42585(12) 0.0438(7) Uani 1 1 d . . . C14 C -1.3620(2) -0.1600(5) -0.22610(10) 0.0362(6) Uani 1 1 d . . . C1 C -1.0009(2) -0.1981(5) -0.39588(10) 0.0367(7) Uani 1 1 d . . . H1 H -1.0182 -0.0503 -0.4161 0.044 Uiso 1 1 calc R . . C11 C -1.2511(2) -0.1915(5) -0.31642(10) 0.0338(6) Uani 1 1 d . . . C5 C -1.1443(2) -0.4137(5) -0.44700(11) 0.0434(7) Uani 1 1 d . . . H5A H -1.1605 -0.5575 -0.4680 0.052 Uiso 1 1 calc R . . H5B H -1.1614 -0.2726 -0.4687 0.052 Uiso 1 1 calc R . . C17 C -1.4690(2) 0.0487(5) -0.16776(12) 0.0490(8) Uani 1 1 d . . . H17A H -1.5294 0.0616 -0.1922 0.073 Uiso 1 1 calc R . . H17B H -1.4255 0.1906 -0.1705 0.073 Uiso 1 1 calc R . . H17C H -1.4925 0.0353 -0.1323 0.073 Uiso 1 1 calc R . . C6 C -1.0292(2) -0.4110(5) -0.43065(11) 0.0432(7) Uani 1 1 d . . . H6A H -0.9879 -0.4051 -0.4620 0.052 Uiso 1 1 calc R . . H6B H -1.0112 -0.5596 -0.4117 0.052 Uiso 1 1 calc R . . C9 C -0.6508(3) -0.1062(7) -0.45801(13) 0.0625(10) Uani 1 1 d . . . H9A H -0.5929 -0.2213 -0.4595 0.075 Uiso 1 1 calc R . . H9B H -0.6876 -0.1015 -0.4926 0.075 Uiso 1 1 calc R . . C18 C -0.8426(2) -0.4163(6) -0.35235(13) 0.0555(9) Uani 1 1 d . . . H18A H -0.7705 -0.3903 -0.3397 0.083 Uiso 1 1 calc R . . H18B H -0.8453 -0.5492 -0.3769 0.083 Uiso 1 1 calc R . . H18C H -0.8853 -0.4533 -0.3230 0.083 Uiso 1 1 calc R . . C10 C -0.6097(3) 0.1298(8) -0.44485(14) 0.0863(14) Uani 1 1 d . . . H10A H -0.5748 0.1254 -0.4102 0.129 Uiso 1 1 calc R . . H10B H -0.6669 0.2447 -0.4451 0.129 Uiso 1 1 calc R . . H10C H -0.5598 0.1773 -0.4705 0.129 Uiso 1 1 calc R . . 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 O4 0.0573(13) 0.0311(10) 0.0531(13) -0.0007(9) 0.0048(10) 0.0038(10) O7 0.0457(12) 0.0538(12) 0.0388(11) 0.0015(9) 0.0144(9) 0.0052(10) N1 0.0405(13) 0.0351(13) 0.0377(13) 0.0007(11) 0.0076(11) 0.0003(11) O5 0.0474(13) 0.0630(14) 0.0595(14) 0.0077(12) -0.0008(10) 0.0049(12) O6 0.0498(13) 0.0598(14) 0.0663(15) -0.0133(12) 0.0086(11) -0.0194(12) O2 0.0477(14) 0.109(2) 0.0646(16) 0.0420(15) 0.0093(12) -0.0045(14) O3 0.0876(18) 0.0518(13) 0.0460(13) -0.0014(11) -0.0189(13) -0.0006(12) O1 0.0423(13) 0.0814(16) 0.0566(14) 0.0165(12) 0.0173(10) 0.0022(12) C16 0.0425(16) 0.0344(14) 0.0374(15) 0.0057(12) 0.0073(13) 0.0011(13) N2 0.0426(15) 0.0517(16) 0.0333(13) -0.0026(11) 0.0094(11) -0.0060(13) C7 0.0395(16) 0.0435(16) 0.0388(16) 0.0005(13) 0.0074(13) -0.0033(13) C15 0.0378(16) 0.0359(14) 0.0450(16) -0.0013(13) 0.0086(13) 0.0026(13) C3 0.0417(16) 0.0316(13) 0.0322(14) 0.0018(11) 0.0075(12) -0.0007(12) C13 0.0436(17) 0.0375(15) 0.0329(14) 0.0038(12) 0.0051(12) -0.0004(13) C2 0.0397(15) 0.0292(13) 0.0335(14) -0.0010(11) 0.0080(12) 0.0011(12) C4 0.0382(16) 0.0371(14) 0.0352(15) -0.0009(12) 0.0076(12) -0.0013(12) C12 0.0352(15) 0.0327(14) 0.0398(16) -0.0018(12) 0.0070(12) 0.0013(12) C8 0.0407(18) 0.0492(17) 0.0423(17) 0.0051(15) 0.0090(14) -0.0053(14) C14 0.0350(15) 0.0420(16) 0.0320(14) -0.0023(12) 0.0057(12) -0.0041(12) C1 0.0383(16) 0.0355(14) 0.0371(15) 0.0034(12) 0.0090(12) 0.0005(12) C11 0.0357(15) 0.0338(14) 0.0323(14) 0.0009(11) 0.0049(12) -0.0023(12) C5 0.0473(18) 0.0489(17) 0.0350(15) -0.0064(13) 0.0114(13) -0.0062(14) C17 0.0498(18) 0.0571(19) 0.0412(17) -0.0044(14) 0.0152(14) 0.0091(15) C6 0.0469(18) 0.0469(16) 0.0371(16) -0.0056(13) 0.0148(13) -0.0029(14) C9 0.049(2) 0.086(3) 0.055(2) 0.0103(19) 0.0216(16) -0.0022(19) C18 0.0417(18) 0.065(2) 0.060(2) 0.0205(17) 0.0122(15) 0.0030(16) C10 0.085(3) 0.125(4) 0.051(2) -0.017(2) 0.025(2) -0.054(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 O4 N1 1.226(3) . ? O7 C14 1.367(3) . ? O7 C17 1.433(3) . ? N1 O3 1.208(3) . ? N1 C2 1.509(3) . ? O5 N2 1.217(3) . ? O6 N2 1.228(3) . ? O2 C8 1.190(4) . ? O1 C8 1.322(4) . ? O1 C9 1.464(3) . ? C16 C11 1.383(4) . ? C16 C15 1.390(4) . ? N2 C4 1.499(4) . ? C7 C8 1.520(4) . ? C7 C18 1.540(4) . ? C7 C1 1.540(4) . ? C15 C14 1.386(4) . ? C3 C11 1.521(3) . ? C3 C4 1.528(4) . ? C3 C2 1.533(4) . ? C13 C12 1.387(4) . ? C13 C14 1.387(4) . ? C2 C1 1.534(3) . ? C4 C5 1.523(4) . ? C12 C11 1.396(4) . ? C1 C6 1.530(4) . ? C5 C6 1.522(4) . ? C9 C10 1.464(5) . ? 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 C14 O7 C17 117.7(2) . . ? O3 N1 O4 124.0(2) . . ? O3 N1 C2 118.0(2) . . ? O4 N1 C2 117.9(2) . . ? C8 O1 C9 117.8(2) . . ? C11 C16 C15 121.9(3) . . ? O5 N2 O6 123.8(3) . . ? O5 N2 C4 119.2(2) . . ? O6 N2 C4 117.0(2) . . ? C8 C7 C18 112.4(2) . . ? C8 C7 C1 110.3(2) . . ? C18 C7 C1 114.4(2) . . ? C14 C15 C16 119.1(3) . . ? C11 C3 C4 113.5(2) . . ? C11 C3 C2 111.5(2) . . ? C4 C3 C2 107.3(2) . . ? C12 C13 C14 120.1(2) . . ? N1 C2 C3 108.3(2) . . ? N1 C2 C1 108.4(2) . . ? C3 C2 C1 113.1(2) . . ? N2 C4 C5 107.5(2) . . ? N2 C4 C3 110.6(2) . . ? C5 C4 C3 112.6(2) . . ? C13 C12 C11 120.6(2) . . ? O2 C8 O1 123.7(3) . . ? O2 C8 C7 124.3(3) . . ? O1 C8 C7 112.0(3) . . ? O7 C14 C15 124.6(2) . . ? O7 C14 C13 115.4(2) . . ? C15 C14 C13 120.0(2) . . ? C6 C1 C2 108.4(2) . . ? C6 C1 C7 112.5(2) . . ? C2 C1 C7 112.3(2) . . ? C16 C11 C12 118.2(2) . . ? C16 C11 C3 120.7(2) . . ? C12 C11 C3 121.1(2) . . ? C6 C5 C4 110.0(2) . . ? C5 C6 C1 111.8(2) . . ? C10 C9 O1 109.8(3) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 62.70 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.227 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.046