#------------------------------------------------------------------------------ #$Date: 2013-12-28 15:58:47 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/02/2200237.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_2200237 loop_ _publ_author_name 'Skakle, Janet M. S.' 'Smyth, Gregory' 'Wardell, Solange M. S. V.' _publ_section_title ; Isopropyl 2-bromo-4-(N-phthalimido)butanoate ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o300 _journal_page_last o302 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C15 H16 Br N O4' _chemical_formula_moiety 'C15 H16 Br N O4' _chemical_formula_sum 'C15 H16 Br N O4' _chemical_formula_weight 354.20 _chemical_name_systematic ; 1-methylethyl 2-bromo-4-(N-phthalimido)butanoate ; _space_group_IT_number 29 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2c -2ac' _symmetry_space_group_name_H-M 'P c a 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 27.307(2) _cell_length_b 4.6228(4) _cell_length_c 12.5888(11) _cell_measurement_reflns_used 2380 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.786 _cell_measurement_theta_min 2.200 _cell_volume 1589.1(2) _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_collection 'SMART (Bruker, 1999)' _computing_data_reduction SAINT _computing_molecular_graphics ; ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEP-3 (Farrugia, 1997) ; _computing_publication_material 'CIFTAB (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full .944 _diffrn_measured_fraction_theta_max .944 _diffrn_measurement_device_type 'Bruker SMART 1000 area CCD detector' _diffrn_measurement_method \f-\w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0819 _diffrn_reflns_av_sigmaI/netI .0913 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 11746 _diffrn_reflns_theta_full 31.05 _diffrn_reflns_theta_max 31.05 _diffrn_reflns_theta_min 1.49 _diffrn_standards_decay_% none _exptl_absorpt_coefficient_mu 2.601 _exptl_absorpt_correction_T_max .4227 _exptl_absorpt_correction_T_min .3563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS: Bruker, 1999)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max .50 _exptl_crystal_size_mid .50 _exptl_crystal_size_min .40 _refine_diff_density_max .704 _refine_diff_density_min -.908 _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack .06(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 187 _refine_ls_number_reflns 4189 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all .1485 _refine_ls_R_factor_gt .0735 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w = 1/[\s^2^(Fo^2^)+(0.0921P)^2^+0.1679P] where P = (Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1960 _reflns_number_gt 2201 _reflns_number_total 4189 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file wn6007.cif _[local]_cod_data_source_block I _cod_original_cell_volume 1589.2(2) _cod_database_code 2200237 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' loop_ _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_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .4073(3) .4301(16) .8873(4) .0444(16) Uani d . 1 . . C C2 .3888(5) .341(2) .9836(8) .077(3) Uani d . 1 . . C H2 .3644 .2010 .9876 .093 Uiso calc R 1 . . H C3 .4078(4) .467(2) 1.0740(7) .069(3) Uani d . 1 . . C H3 .3955 .4115 1.1397 .083 Uiso calc R 1 . . H C4 .4442(4) .673(3) 1.0705(7) .080(3) Uani d . 1 . . C H4 .4568 .7483 1.1334 .095 Uiso calc R 1 . . H C5 .4623(4) .768(2) .9733(7) .067(3) Uani d . 1 . . C H5 .4860 .9123 .9693 .080 Uiso calc R 1 . . H C6 .4435(3) .6398(14) .8831(6) .0439(18) Uani d . 1 . . C C7 .4546(3) .6942(17) .7689(6) .0440(18) Uani d . 1 . . C O1 .4820(2) .8742(12) .7298(4) .0612(16) Uani d . 1 . . O C8 .3959(3) .3480(15) .7769(6) .044(2) Uani d . 1 . . C O2 .3689(2) .1466(11) .7456(4) .0644(16) Uani d . 1 . . O N1 .4251(2) .5059(13) .7104(5) .0452(14) Uani d . 1 . . N C9 .4238(3) .4853(19) .5940(5) .0508(18) Uani d . 1 . . C H9A .4248 .2838 .5726 .061 Uiso calc R 1 . . H H9B .4522 .5819 .5641 .061 Uiso calc R 1 . . H C10 .3771(3) .6267(15) .5529(5) .0407(16) Uani d . 1 . . C H10A .3491 .5302 .5842 .049 Uiso calc R 1 . . H H10B .3765 .8273 .5755 .049 Uiso calc R 1 . . H C11 .3729(3) .6141(14) .4329(5) .0421(17) Uani d . 1 . . C H11 .3709 .4132 .4085 .051 Uiso calc R 1 . . H Br1 .42793(3) .81925(18) .36266(6) .0632(3) Uani d . 1 . . Br C12 .3294(3) .7847(17) .3949(6) .0485(19) Uani d . 1 . . C O3 .3117(2) .9855(14) .4376(5) .0689(17) Uani d . 1 . . O O4 .3113(2) .6718(13) .3039(5) .0646(16) Uiso d . 1 . . O C13 .2687(4) .816(2) .2576(9) .085(3) Uani d . 1 . . C H13 .2696 1.0238 .2730 .102 Uiso calc R 1 . . H C14 .2240(4) .683(3) .3032(13) .132(6) Uani d . 1 . . C H14A .2292 .4791 .3124 .198 Uiso calc R 1 . . H H14B .1969 .7136 .2559 .198 Uiso calc R 1 . . H H14C .2170 .7701 .3707 .198 Uiso calc R 1 . . H C15 .2731(8) .764(5) .1401(13) .170(8) Uani d . 1 . . C H15A .3023 .8539 .1139 .254 Uiso calc R 1 . . H H15B .2451 .8440 .1046 .254 Uiso calc R 1 . . H H15C .2745 .5593 .1268 .254 Uiso calc R 1 . . H 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 C1 .066(4) .047(3) .019(4) .002(3) .001(3) .004(3) C2 .112(9) .074(6) .046(5) .001(6) .019(6) .022(5) C3 .104(8) .077(6) .026(4) .018(6) .011(5) .000(4) C4 .084(7) .118(9) .037(4) .022(7) -.005(4) -.011(6) C5 .088(8) .091(7) .021(4) -.009(6) -.015(4) -.013(4) C6 .047(4) .044(4) .041(5) .006(3) .001(3) .003(3) C7 .044(4) .049(4) .039(4) -.003(4) .001(3) .024(4) O1 .094(5) .052(3) .037(3) -.011(3) .001(3) .005(2) C8 .067(5) .025(3) .041(4) -.008(3) .010(4) .006(3) O2 .104(5) .049(3) .040(3) -.019(3) .011(3) -.002(3) N1 .056(4) .053(4) .027(3) -.004(3) .003(3) .005(3) C9 .064(5) .066(5) .022(3) -.001(4) .000(3) -.003(3) C10 .057(4) .042(4) .023(3) -.001(3) .001(3) .000(3) C11 .066(5) .036(4) .024(3) -.010(3) .000(3) -.004(3) Br1 .0657(5) .0917(5) .0322(3) -.0122(4) .0082(5) .0038(6) C12 .055(5) .050(4) .040(4) -.016(4) -.007(3) -.001(3) O3 .075(4) .068(4) .063(4) .012(3) -.008(3) -.021(3) C13 .097(8) .077(6) .082(7) .033(6) -.048(6) -.022(6) C14 .059(7) .156(12) .181(17) .040(8) -.018(8) -.047(11) C15 .202(18) .24(2) .068(9) .039(16) -.073(11) -.010(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.376(11) ? C1 C6 . 1.384(11) ? C1 C8 . 1.474(10) ? C2 C3 . 1.380(16) ? C2 H2 . .9300 ? C3 C4 . 1.377(15) ? C3 H3 . .9300 ? C4 C5 . 1.391(14) ? C4 H4 . .9300 ? C5 C6 . 1.382(11) ? C5 H5 . .9300 ? C6 C7 . 1.491(10) ? C7 O1 . 1.223(9) ? C7 N1 . 1.396(11) ? C8 O2 . 1.252(10) ? C8 N1 . 1.366(9) ? N1 C9 . 1.468(9) ? C9 C10 . 1.524(10) ? C9 H9A . .9700 ? C9 H9B . .9700 ? C10 C11 . 1.516(8) ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 C12 . 1.504(11) ? C11 Br1 . 1.985(7) ? C11 H11 . .9800 ? C12 O3 . 1.176(9) ? C12 O4 . 1.353(8) ? O4 C13 . 1.462(11) ? C13 C14 . 1.482(19) ? C13 C15 . 1.504(19) ? C13 H13 . .9800 ? C14 H14A . .9600 ? C14 H14B . .9600 ? C14 H14C . .9600 ? C15 H15A . .9600 ? C15 H15B . .9600 ? C15 H15C . .9600 ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C2 C1 C6 120.4(8) C2 C1 C8 132.5(8) C6 C1 C8 107.1(6) C1 C2 C3 117.4(11) C1 C2 H2 121.3 C3 C2 H2 121.3 C4 C3 C2 122.5(9) C4 C3 H3 118.7 C2 C3 H3 118.7 C3 C4 C5 120.2(9) C3 C4 H4 119.9 C5 C4 H4 119.9 C6 C5 C4 117.1(10) C6 C5 H5 121.5 C4 C5 H5 121.5 C5 C6 C1 122.3(7) C5 C6 C7 130.1(7) C1 C6 C7 107.5(6) O1 C7 N1 124.5(7) O1 C7 C6 128.8(8) N1 C7 C6 106.6(6) O2 C8 N1 123.3(7) O2 C8 C1 127.7(7) N1 C8 C1 108.5(6) C8 N1 C7 110.3(6) C8 N1 C9 124.2(7) C7 N1 C9 125.4(6) N1 C9 C10 109.3(6) N1 C9 H9A 109.8 C10 C9 H9A 109.8 N1 C9 H9B 109.8 C10 C9 H9B 109.8 H9A C9 H9B 108.3 C11 C10 C9 112.7(6) C11 C10 H10A 109.1 C9 C10 H10A 109.1 C11 C10 H10B 109.1 C9 C10 H10B 109.1 H10A C10 H10B 107.8 C12 C11 C10 110.9(6) C12 C11 Br1 101.9(4) C10 C11 Br1 111.6(5) C12 C11 H11 110.7 C10 C11 H11 110.7 Br1 C11 H11 110.7 O3 C12 O4 122.8(8) O3 C12 C11 126.4(7) O4 C12 C11 110.8(7) C12 O4 C13 116.8(7) O4 C13 C14 108.2(10) O4 C13 C15 104.8(10) C14 C13 C15 112.2(12) O4 C13 H13 110.5 C14 C13 H13 110.5 C15 C13 H13 110.5 C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 H15A C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 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 C9 H9B Br1 . .97 2.84 3.299(7) 109.8 C11 H11 O3 1_545 .98 2.58 3.353(9) 135.7 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 -.3(14) C8 C1 C2 C3 -179.3(9) C1 C2 C3 C4 -.7(15) C2 C3 C4 C5 2.1(16) C3 C4 C5 C6 -2.5(15) C4 C5 C6 C1 1.5(13) C4 C5 C6 C7 179.4(9) C2 C1 C6 C5 -.1(13) C8 C1 C6 C5 179.1(8) C2 C1 C6 C7 -178.4(8) C8 C1 C6 C7 .8(8) C5 C6 C7 O1 -2.8(14) C1 C6 C7 O1 175.3(8) C5 C6 C7 N1 -179.7(9) C1 C6 C7 N1 -1.7(8) C2 C1 C8 O2 -8.5(15) C6 C1 C8 O2 172.5(8) C2 C1 C8 N1 179.4(10) C6 C1 C8 N1 .3(9) O2 C8 N1 C7 -174.0(8) C1 C8 N1 C7 -1.4(9) O2 C8 N1 C9 8.1(12) C1 C8 N1 C9 -179.4(7) O1 C7 N1 C8 -175.2(8) C6 C7 N1 C8 1.9(8) O1 C7 N1 C9 2.7(13) C6 C7 N1 C9 179.8(7) C8 N1 C9 C10 72.3(9) C7 N1 C9 C10 -105.3(8) N1 C9 C10 C11 -179.9(6) C9 C10 C11 C12 -173.6(6) C9 C10 C11 Br1 -60.7(7) C10 C11 C12 O3 27.7(11) Br1 C11 C12 O3 -91.1(8) C10 C11 C12 O4 -150.5(6) Br1 C11 C12 O4 90.6(5) O3 C12 O4 C13 1.6(12) C11 C12 O4 C13 179.9(8) C12 O4 C13 C14 -89.4(10) C12 O4 C13 C15 150.6(11) _cod_database_fobs_code 2200237 _journal_paper_doi 10.1107/S1600536801003816