data_luc39 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 4-iodophenylalanine monohydrate ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H10 I N O2, H2 O' _chemical_formula_sum 'C9 H12 I N O3' _chemical_formula_weight 309.10 _chemical_absolute_configuration rmad 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' 'I' 'I' -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _space_group_IT_number 4 _space_group_name_H-M_alt 'P 21' _space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.2312(5) _cell_length_b 5.2898(4) _cell_length_c 16.4690(13) _cell_angle_alpha 90.00 _cell_angle_beta 96.772(4) _cell_angle_gamma 90.00 _cell_volume 539.06(7) _cell_formula_units_Z 2 _cell_measurement_temperature 103(2) _cell_measurement_reflns_used 7266 _cell_measurement_theta_min 2.49 _cell_measurement_theta_max 33.28 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_max 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 300 _exptl_absorpt_coefficient_mu 2.953 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.' _exptl_absorpt_correction_T_min 0.4380 _exptl_absorpt_correction_T_max 0.5769 _exptl_special_details ; Bruker KRYOFLEX low temperature device. ; _diffrn_ambient_temperature 103(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_decay_% 0.00 _diffrn_reflns_number 14156 _diffrn_reflns_av_R_equivalents 0.0389 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.49 _diffrn_reflns_theta_max 35.65 _reflns_number_total 4466 _reflns_number_gt 4109 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ; SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122) ; _computing_structure_refinement ; SHELXL (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122) ; _computing_molecular_graphics ; ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565) Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457 ; _computing_publication_material 'SHELXL' _iucr_refine_instructions_details ; TITL luc39 in P2(1) CELL 0.71073 6.2312 5.2898 16.4690 90.000 96.772 90.000 ZERR 2.00 0.0005 0.0004 0.0013 0.000 0.004 0.000 LATT -1 SYMM -X, 0.5+Y, -Z SFAC C H N O I UNIT 18 24 2 6 2 L.S. 4 BOND $H CONF HTAB EQIV $1 2-x,-1/2+y,1-z RTAB DIST I1 I1_$1 RTAB ANGL C3 I1 I1_$1 ACTA omit -1 0 4 FMAP 2 PLAN 40 SIZE 0.050 0.080 0.360 DFIX 0.85 O1W H1W O1W H2W SADI N1 H1N N1 H2N N1 H3N SADI H1N H2N H1N H3N H2N H3N SADI C8 H1N C8 H2N C8 H3N TEMP -170.000 WGHT 0.028500 1.332700 FVAR 0.21503 MOLE 1 I1 5 0.866921 -0.255018 0.430613 11.00000 0.01921 0.01313 = 0.01552 0.00097 -0.00349 0.00136 O1 4 -0.077237 0.522273 0.065351 11.00000 0.01159 0.01060 = 0.02044 0.00000 -0.00479 0.00001 O2 4 0.065750 0.204153 0.143670 11.00000 0.01527 0.00446 = 0.01961 0.00124 0.00132 -0.00288 O1W 4 0.698250 0.961486 0.066368 11.00000 0.01119 0.01302 = 0.02213 -0.00095 -0.00040 -0.00105 N1 3 0.282331 0.803039 0.084227 11.00000 0.00775 0.01104 = 0.01755 0.00225 0.00011 -0.00026 H1N 2 0.221048 0.802491 0.034484 11.00000 -1.50000 H2N 2 0.402452 0.876940 0.077818 11.00000 -1.50000 H3N 2 0.214840 0.929542 0.103161 11.00000 -1.50000 C1 1 0.657046 0.314012 0.248597 11.00000 0.01277 0.01614 = 0.01546 0.00016 0.00174 0.00020 AFIX 43 H1 2 0.713195 0.385395 0.202556 11.00000 -1.20000 AFIX 0 C2 1 0.773658 0.127712 0.293016 11.00000 0.01184 0.01646 = 0.01394 0.00095 -0.00014 -0.00013 AFIX 43 H2 2 0.907924 0.070872 0.277811 11.00000 -1.20000 AFIX 0 C3 1 0.689673 0.024442 0.360949 11.00000 0.01586 0.01366 = 0.01372 0.00048 -0.00203 0.00110 C4 1 0.491837 0.106499 0.382797 11.00000 0.01384 0.01760 = 0.01736 0.00243 0.00251 0.00059 AFIX 43 H4 2 0.435470 0.034804 0.428744 11.00000 -1.20000 AFIX 0 C5 1 0.378665 0.291798 0.337488 11.00000 0.01499 0.01527 = 0.01642 0.00126 0.00510 0.00197 AFIX 43 H5 2 0.243798 0.347223 0.352516 11.00000 -1.20000 AFIX 0 C6 1 0.458923 0.400355 0.269479 11.00000 0.01072 0.01407 = 0.01464 -0.00038 -0.00257 -0.00108 C7 1 0.341501 0.614422 0.222490 11.00000 0.01238 0.01082 = 0.01315 -0.00043 -0.00151 -0.00090 AFIX 23 H7A 2 0.431534 0.768796 0.229769 11.00000 -1.20000 H7B 2 0.205057 0.648310 0.245848 11.00000 -1.20000 AFIX 0 C8 1 0.288723 0.560814 0.130244 11.00000 0.01009 0.00850 = 0.01350 0.00193 0.00036 0.00099 AFIX 13 H8 2 0.406766 0.453633 0.112386 11.00000 -1.20000 AFIX 0 C9 1 0.073414 0.418414 0.110896 11.00000 0.00867 0.01076 = 0.01351 -0.00245 0.00118 -0.00059 H1W 2 0.782225 1.048007 0.098635 11.00000 0.02776 H2W 2 0.779732 0.845249 0.053793 11.00000 0.02956 HKLF 4 REM luc39 in P2(1) REM R1 = 0.0368 for 4109 Fo > 4sig(Fo) and 0.0415 for all 4466 data REM 144 parameters refined using 12 restraints END WGHT 0.0285 1.3328 REM Highest difference peak 4.454, deepest hole -1.695, 1-sigma level 0.166 Q1 1 0.9606 -0.2546 0.4016 11.00000 0.05 4.45 Q2 1 0.2945 -0.2511 0.4306 11.00000 0.05 1.86 Q3 1 1.0707 0.2440 0.2935 11.00000 0.05 1.33 Q4 1 0.4507 -0.0405 0.4726 11.00000 0.05 0.91 Q5 1 0.7031 0.2468 0.2774 11.00000 0.05 0.89 Q6 1 0.8237 -0.2551 0.3806 11.00000 0.05 0.87 Q7 1 0.8233 -0.1445 0.4624 11.00000 0.05 0.86 Q8 1 0.5480 -0.1220 0.4812 11.00000 0.05 0.86 Q9 1 0.7550 -0.2528 0.4642 11.00000 0.05 0.85 Q10 1 0.8979 -0.2507 0.4830 11.00000 0.05 0.81 Q11 1 0.5074 -0.2586 0.4281 11.00000 0.05 0.80 Q12 1 0.9115 -0.0970 0.3323 11.00000 0.05 0.77 Q13 1 0.8361 -0.3640 0.4680 11.00000 0.05 0.75 Q14 1 0.3386 0.7477 0.1508 11.00000 0.05 0.73 Q15 1 0.5284 0.0403 0.5257 11.00000 0.05 0.67 Q16 1 0.9269 -0.4125 0.3287 11.00000 0.05 0.67 Q17 1 0.8509 -0.2523 0.3510 11.00000 0.05 0.66 Q18 1 0.9824 -0.2541 0.4517 11.00000 0.05 0.65 Q19 1 0.4459 0.2464 0.3725 11.00000 0.05 0.57 Q20 1 0.5864 0.4079 0.3717 11.00000 0.05 0.52 Q21 1 0.7360 0.0692 0.3316 11.00000 0.05 0.52 Q22 1 0.5815 0.0576 0.3634 11.00000 0.05 0.50 Q23 1 0.5642 0.3518 0.2567 11.00000 0.05 0.50 Q24 1 0.2764 0.2527 0.2541 11.00000 0.05 0.50 Q25 1 0.4149 0.2079 0.2830 11.00000 0.05 0.48 Q26 1 0.1002 0.2409 0.1793 11.00000 0.05 0.47 Q27 1 0.1579 0.2434 0.1696 11.00000 0.05 0.47 Q28 1 0.4165 0.2696 0.2806 11.00000 0.05 0.46 Q29 1 0.6803 0.7538 0.1448 11.00000 0.05 0.45 Q30 1 0.4765 0.7457 -0.0150 11.00000 0.05 0.45 Q31 1 0.8653 -0.3080 0.2978 11.00000 0.05 0.44 Q32 1 0.7765 -0.4973 0.4814 11.00000 0.05 0.44 Q33 1 0.5658 0.1486 0.2521 11.00000 0.05 0.44 Q34 1 0.0156 1.0054 0.0687 11.00000 0.05 0.43 Q35 1 0.1371 0.2381 0.1301 11.00000 0.05 0.42 Q36 1 0.0678 0.1167 0.1500 11.00000 0.05 0.42 Q37 1 0.4310 0.2505 0.3100 11.00000 0.05 0.42 Q38 1 0.2133 0.4950 0.2202 11.00000 0.05 0.41 Q39 1 0.6160 0.5165 0.0495 11.00000 0.05 0.40 Q40 1 0.0177 0.4954 0.0618 11.00000 0.05 0.40 ; _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. The water aatoms were derived from a difference map and restrained to have similar O-H distance. Also aminic H atoms were found on a difference map; they were refined with restraints both on N1-H H...H and C8...H distances. The reflection -1,0,4 havind a w\D^2^ larger than 10 was omitted from the refinement. A large residue at 0.80 \%A from I1 may indicate an insufficient absorption correction or a possible unadequancy of the ADPs to describe the real motion of the iodine atom. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+1.3327P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(3) _refine_ls_number_reflns 4466 _refine_ls_number_parameters 144 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0368 _refine_ls_wR_factor_ref 0.0840 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.110 _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 I1 I 0.86692(3) -0.25502(6) 0.430613(12) 0.01639(6) Uani 1 1 d . . . O1 O -0.0772(4) 0.5223(5) 0.06535(18) 0.0147(5) Uani 1 1 d . . . O2 O 0.0657(4) 0.2042(4) 0.14367(17) 0.0132(6) Uani 1 1 d . . . O1W O 0.6982(5) 0.9615(6) 0.06637(19) 0.0156(5) Uani 1 1 d D . . N1 N 0.2823(5) 0.8030(5) 0.0842(2) 0.0122(6) Uani 1 1 d D . . H1N H 0.221(6) 0.802(7) 0.034(2) 0.018 Uiso 1 1 d D . . H2N H 0.402(6) 0.877(7) 0.078(2) 0.018 Uiso 1 1 d D . . H3N H 0.215(6) 0.930(6) 0.103(2) 0.018 Uiso 1 1 d D . . C1 C 0.6570(6) 0.3140(7) 0.2486(2) 0.0148(7) Uani 1 1 d . . . H1 H 0.7132 0.3854 0.2026 0.018 Uiso 1 1 calc R . . C2 C 0.7737(6) 0.1277(7) 0.2930(2) 0.0142(6) Uani 1 1 d . . . H2 H 0.9079 0.0709 0.2778 0.017 Uiso 1 1 calc R . . C3 C 0.6897(7) 0.0244(7) 0.3609(2) 0.0147(6) Uani 1 1 d . . . C4 C 0.4918(6) 0.1065(8) 0.3828(2) 0.0162(7) Uani 1 1 d . . . H4 H 0.4355 0.0348 0.4287 0.019 Uiso 1 1 calc R . . C5 C 0.3787(6) 0.2918(6) 0.3375(2) 0.0153(8) Uani 1 1 d . . . H5 H 0.2438 0.3472 0.3525 0.018 Uiso 1 1 calc R . . C6 C 0.4589(6) 0.4004(7) 0.2695(2) 0.0135(6) Uani 1 1 d . . . C7 C 0.3415(6) 0.6144(7) 0.2225(2) 0.0124(6) Uani 1 1 d . . . H7A H 0.4315 0.7688 0.2298 0.015 Uiso 1 1 calc R . . H7B H 0.2051 0.6483 0.2458 0.015 Uiso 1 1 calc R . . C8 C 0.2887(6) 0.5608(6) 0.1302(2) 0.0108(6) Uani 1 1 d D . . H8 H 0.4068 0.4536 0.1124 0.013 Uiso 1 1 calc R . . C9 C 0.0734(6) 0.4184(7) 0.1109(2) 0.0110(6) Uani 1 1 d . . . H1W H 0.782(8) 1.048(10) 0.099(3) 0.028(16) Uiso 1 1 d D . . H2W H 0.780(8) 0.845(9) 0.054(4) 0.030(17) Uiso 1 1 d 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 I1 0.01921(10) 0.01313(8) 0.01552(9) 0.00097(16) -0.00349(6) 0.00136(14) O1 0.0116(12) 0.0106(11) 0.0204(13) 0.0000(9) -0.0048(10) 0.0000(9) O2 0.0153(11) 0.0045(16) 0.0196(11) 0.0012(9) 0.0013(9) -0.0029(8) O1W 0.0112(12) 0.0130(12) 0.0221(13) -0.0010(10) -0.0004(10) -0.0011(9) N1 0.0077(12) 0.0110(15) 0.0175(13) 0.0022(9) 0.0001(10) -0.0003(8) C1 0.0128(15) 0.0161(15) 0.0155(15) 0.0002(11) 0.0017(12) 0.0002(11) C2 0.0118(16) 0.0165(17) 0.0139(15) 0.0009(12) -0.0001(12) -0.0001(12) C3 0.0159(16) 0.0137(15) 0.0137(15) 0.0005(12) -0.0020(12) 0.0011(12) C4 0.0138(16) 0.0176(17) 0.0174(16) 0.0024(13) 0.0025(13) 0.0006(13) C5 0.0150(15) 0.015(2) 0.0164(14) 0.0013(11) 0.0051(12) 0.0020(11) C6 0.0107(15) 0.0141(15) 0.0146(15) -0.0004(12) -0.0026(12) -0.0011(12) C7 0.0124(15) 0.0108(14) 0.0132(15) -0.0004(11) -0.0015(12) -0.0009(11) C8 0.0101(14) 0.0085(14) 0.0135(14) 0.0019(11) 0.0004(11) 0.0010(11) C9 0.0087(14) 0.0108(15) 0.0135(14) -0.0024(12) 0.0012(11) -0.0006(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag I1 C3 2.103(4) . ? O1 C9 1.257(4) . ? O2 C9 1.259(4) . ? O1W H1W 0.837(19) . ? O1W H2W 0.839(19) . ? N1 C8 1.487(4) . ? N1 H1N 0.86(3) . ? N1 H2N 0.86(3) . ? N1 H3N 0.87(3) . ? C1 C2 1.382(5) . ? C1 C6 1.397(5) . ? C1 H1 0.9500 . ? C2 C3 1.401(5) . ? C2 H2 0.9500 . ? C3 C4 1.394(6) . ? C4 C5 1.375(5) . ? C4 H4 0.9500 . ? C5 C6 1.402(5) . ? C5 H5 0.9500 . ? C6 C7 1.511(5) . ? C7 C8 1.542(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.539(5) . ? C8 H8 1.0000 . ? 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 H1W O1W H2W 102(6) . . ? C8 N1 H1N 118(2) . . ? C8 N1 H2N 119(3) . . ? H1N N1 H2N 100(3) . . ? C8 N1 H3N 118(2) . . ? H1N N1 H3N 99(3) . . ? H2N N1 H3N 99(3) . . ? C2 C1 C6 121.9(4) . . ? C2 C1 H1 119.1 . . ? C6 C1 H1 119.1 . . ? C1 C2 C3 118.6(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 120.7(4) . . ? C4 C3 I1 120.1(3) . . ? C2 C3 I1 119.2(3) . . ? C5 C4 C3 119.6(4) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C7 120.5(3) . . ? C5 C6 C7 121.3(3) . . ? C6 C7 C8 113.6(3) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? N1 C8 C9 110.2(3) . . ? N1 C8 C7 109.5(3) . . ? C9 C8 C7 111.9(3) . . ? N1 C8 H8 108.4 . . ? C9 C8 H8 108.4 . . ? C7 C8 H8 108.4 . . ? O1 C9 O2 125.9(3) . . ? O1 C9 C8 118.8(3) . . ? O2 C9 C8 115.4(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.2(6) . . . . ? C1 C2 C3 C4 0.5(6) . . . . ? C1 C2 C3 I1 -179.0(3) . . . . ? C2 C3 C4 C5 -0.4(6) . . . . ? I1 C3 C4 C5 179.1(3) . . . . ? C3 C4 C5 C6 0.0(6) . . . . ? C2 C1 C6 C5 -0.2(6) . . . . ? C2 C1 C6 C7 176.6(3) . . . . ? C4 C5 C6 C1 0.4(6) . . . . ? C4 C5 C6 C7 -176.4(4) . . . . ? C1 C6 C7 C8 58.4(5) . . . . ? C5 C6 C7 C8 -125.0(4) . . . . ? C6 C7 C8 N1 -151.0(3) . . . . ? C6 C7 C8 C9 86.4(4) . . . . ? N1 C8 C9 O1 -3.8(5) . . . . ? C7 C8 C9 O1 118.3(4) . . . . ? N1 C8 C9 O2 176.6(3) . . . . ? C7 C8 C9 O2 -61.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 4.454 _refine_diff_density_min -1.695 _refine_diff_density_rms 0.166