#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/52/4115234.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4115234
loop_
_publ_author_name
'Bo Liu'
'Reema K. Thalji'
'Paul D. Adams'
'Frank R. Fronczek'
'Mark L. McLaughlin'
'Mary D. Barkley'
_publ_section_title
;
 Fluorescence ofcis-1-Amino-2-(3-indolyl)cyclohexane-1-carboxylic Acid: A
 Single Tryptophan χ1Rotamer Model
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13329
_journal_page_last               13338
_journal_paper_doi               10.1021/ja016542d
_journal_volume                  124
_journal_year                    2002
_chemical_compound_source        'local laboratory'
_chemical_formula_moiety         'C15 H20 N2 O2, H2 O'
_chemical_formula_sum            'C15 H20 N2 O3'
_chemical_formula_weight         276.34
_chemical_melting_point          579(1)
_chemical_name_systematic
; 
α-1-ammmonium-2(3-indolyl)-cyclohexanecarboxylate monohydrate
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1293(6)
_cell_length_b                   10.428(1)
_cell_length_c                   13.195(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    299
_cell_measurement_theta_max      43.5
_cell_measurement_theta_min      21.0
_cell_volume                     1393.77(19)
_computing_cell_refinement       CAD4_(Enraf-Nonius,_1994)
_computing_data_collection       CAD4_(Enraf-Nonius,_1994)
_computing_data_reduction        process_MolEN_(Fair,_1990)
_computing_publication_material  BTABLE_PTABLE_CIF_IN_MolEN_(Fair,_1990)
_computing_structure_refinement  LSFM_MolEN_(Fair,_1990)
_computing_structure_solution    direct_methods_(SIR,_Burla_et_al.,_1989)
_diffrn_ambient_temperature      299
_diffrn_measurement_device       Enraf_Nonius_CAD4
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         sealed_tube
_diffrn_radiation_type           Cu-K\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.006
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6184
_diffrn_reflns_theta_max         75.0
_diffrn_reflns_theta_min         2.5
_diffrn_standards_decay_%        0.7
_diffrn_standards_interval_time  126
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_type
;
psi_scans (North, Phillips, Mathews, 1968)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    none
_exptl_crystal_description       fragment
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.207
_refine_ls_abs_structure_details '1074 Friedel pairs (Flack, 1983)'
_refine_ls_abs_structure_Flack   0.37(18)
_refine_ls_extinction_coef       4.3(2)E-6
_refine_ls_extinction_method     isotropic_(Zachariasen,_1963)
_refine_ls_goodness_of_fit_all   1.639
_refine_ls_goodness_of_fit_obs   1.636
_refine_ls_hydrogen_treatment    refined_isotropically
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2733
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.032
_refine_ls_R_factor_obs          0.030
_refine_ls_shift/esd_max         0.006
_refine_ls_shift/esd_mean        0.003
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 4Fo²/(σ²(Fo²) + 0.0004 Fo⁴)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.038
_refine_ls_wR_factor_obs         0.038
_reflns_number_observed          2733
_reflns_number_total             2843
_reflns_observed_criterion       >1.0\s(I)
_cod_data_source_file            ja016542d-2_s1.cif
_cod_data_source_block           W3(alpha)
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value '4Fo^2^/(\s^2^(Fo^2^) + 0.0004
Fo^4^)' was changed to 'calc'. New tag '_refine_ls_weighting_details'
was created. The value of the new tag was set to 'w =
4Fo^2^/(\s^2^(Fo^2^) + 0.0004 Fo^4^)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1393.8(3)
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               4115234
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,-y,1/2+z
-x,1/2+y,1/2-z
1/2+x,1/2-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_type_symbol
O1 0.18156(9) 0.2669(1) 0.31303(8) 0.0494(5) Uij O
O2 0.15183(9) 0.3130(1) 0.47630(8) 0.0518(5) Uij O
O3 0.4399(1) 0.2672(1) 0.28576(9) 0.0587(6) Uij O
N1 0.0822(1) -0.1000(1) 0.6016(1) 0.0584(7) Uij n
N2 -0.0935(1) 0.2532(1) 0.48301(8) 0.0411(5) Uij n
C1 0.2017(1) -0.0914(1) 0.5532(1) 0.0497(7) Uij C
C2 0.3264(2) -0.1365(2) 0.5836(1) 0.0619(8) Uij C
C3 0.4300(2) -0.1147(2) 0.5193(1) 0.0632(9) Uij C
C4 0.4132(1) -0.0501(2) 0.4272(1) 0.0568(8) Uij C
C5 0.2901(1) -0.0061(1) 0.3972(1) 0.0463(7) Uij C
C6 0.1819(1) -0.0259(1) 0.4612(1) 0.0406(6) Uij C
C7 0.0433(1) 0.0041(1) 0.45517(9) 0.0396(6) Uij C
C8 -0.0120(2) -0.0439(1) 0.5412(1) 0.0508(7) Uij C
C9 -0.0263(1) 0.0735(1) 0.37024(9) 0.0351(5) Uij C
C10 -0.1658(1) 0.0207(1) 0.3514(1) 0.0435(6) Uij C
C11 -0.2328(2) 0.0879(2) 0.2629(1) 0.0536(8) Uij C
C12 -0.2387(1) 0.2319(2) 0.2789(1) 0.0501(7) Uij C
C13 -0.1014(1) 0.2872(1) 0.2978(1) 0.0445(6) Uij C
C14 -0.0276(1) 0.2210(1) 0.38462(9) 0.0339(5) Uij C
C15 0.1152(1) 0.2728(1) 0.3920(1) 0.0370(5) Uij C
H2Na -0.181(2) 0.221(2) 0.492(1) 0.074(6) Uiso H
H2Nb -0.095(2) 0.344(2) 0.489(1) 0.064(5) Uiso H
H2 0.331(2) -0.184(2) 0.654(1) 0.086(6) Uiso H
H2Nc -0.044(2) 0.216(2) 0.541(1) 0.082(6) Uiso H
H3wa 0.354(2) 0.287(2) 0.301(2) 0.134(9) Uiso H
H3wb 0.476(2) 0.349(2) 0.269(2) 0.113(7) Uiso H
H3 0.521(2) -0.139(2) 0.544(1) 0.078(6) Uiso H
H4 0.494(2) -0.037(2) 0.381(1) 0.063(5) Uiso H
H5 0.280(1) 0.035(1) 0.336(1) 0.043(4) Uiso H
H8 -0.112(2) -0.049(2) 0.565(1) 0.066(5) Uiso H
H9 0.026(1) 0.059(1) 0.3054(9) 0.034(3) Uiso H
H10a -0.218(1) 0.026(1) 0.4166(9) 0.037(3) Uiso H
H10b -0.153(2) -0.073(1) 0.337(1) 0.057(5) Uiso H
H1N1 0.064(1) -0.137(2) 0.659(1) 0.062(5) Uiso H
H11a -0.191(1) 0.063(1) 0.197(1) 0.054(5) Uiso H
H11b -0.323(2) 0.046(2) 0.249(1) 0.067(5) Uiso H
H12a -0.275(2) 0.273(1) 0.220(1) 0.055(5) Uiso H
H12b -0.294(1) 0.254(2) 0.339(1) 0.057(5) Uiso H
H13b -0.053(1) 0.280(1) 0.236(1) 0.060(5) Uiso H
H13a -0.106(1) 0.379(1) 0.314(1) 0.045(4) Uiso H
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.017 0.009 International_Tables_Vol_IV_Table_2.3.1
H 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1
N 0.029 0.018 International_Tables_Vol_IV_Table_2.3.1
O 0.047 0.032 International_Tables_Vol_IV_Table_2.3.1
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-4 -1 -3
2 -2 -5
-2 -8 5
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
H3wa O3 H3wb 102(2)
C1 N1 C8 108.3(1)
C1 N1 H1N1 129(1)
C8 N1 H1N1 123(1)
C14 N2 H2Na 116(1)
C14 N2 H2Nb 107.4(9)
C14 N2 H2Nc 110(1)
H2Na N2 H2Nb 108(1)
H2Na N2 H2Nc 104(1)
H2Nb N2 H2Nc 109(1)
N1 C1 C2 129.6(1)
N1 C1 C6 107.9(1)
C2 C1 C6 122.4(1)
C1 C2 C3 117.2(2)
C1 C2 H2 116.4(9)
C3 C2 H2 126.5(9)
C2 C3 C4 121.6(1)
C2 C3 H3 117(1)
C4 C3 H3 120(1)
C3 C4 C5 121.2(1)
C3 C4 H4 118.7(9)
C5 C4 H4 120.1(9)
C4 C5 C6 118.9(1)
C4 C5 H5 120.3(9)
C6 C5 H5 120.8(9)
C1 C6 C5 118.8(1)
C1 C6 C7 107.0(1)
C5 C6 C7 134.2(1)
C6 C7 C8 106.0(1)
C6 C7 C9 126.9(1)
C8 C7 C9 127.1(1)
N1 C8 C7 110.7(1)
N1 C8 H8 117.8(9)
C7 C8 H8 131.4(9)
C7 C9 C10 112.2(1)
C7 C9 C14 112.9(1)
C7 C9 H9 108.2(7)
C10 C9 C14 111.5(1)
C10 C9 H9 106.9(7)
C14 C9 H9 104.6(7)
C9 C10 C11 111.7(1)
C9 C10 H10a 108.9(7)
C9 C10 H10b 105.4(9)
C11 C10 H10a 113.0(7)
C11 C10 H10b 111.1(9)
H10a C10 H10b 106(1)
C10 C11 C12 111.5(1)
C10 C11 H11a 110.9(8)
C10 C11 H11b 109.4(9)
C12 C11 H11a 113.1(9)
C12 C11 H11b 114.4(9)
H11a C11 H11b 96(1)
C11 C12 C13 111.1(1)
C11 C12 H12a 110.0(9)
C11 C12 H12b 111(1)
C13 C12 H12a 108.1(9)
C13 C12 H12b 107.1(9)
H12a C12 H12b 109(1)
C12 C13 C14 113.4(1)
C12 C13 H13b 107.6(9)
C12 C13 H13a 111.3(8)
C14 C13 H13b 110.3(9)
C14 C13 H13a 107.1(8)
H13b C13 H13a 106(1)
N2 C14 C9 109.39(9)
N2 C14 C13 109.2(1)
N2 C14 C15 106.49(9)
C9 C14 C13 111.1(1)
C9 C14 C15 110.25(9)
C13 C14 C15 110.3(1)
O1 C15 O2 127.3(1)
O1 C15 C14 115.8(1)
O2 C15 C14 116.9(1)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.242(2)
O2 C15 1.245(2)
O3 H3wa 0.92(2)
O3 H3wb 0.96(2)
N1 C1 1.372(2)
N1 C8 1.374(2)
N1 H1N1 0.88(2)
N2 C14 1.498(2)
N2 H2Na 0.96(2)
N2 H2Nb 0.95(2)
N2 H2Nc 0.99(2)
C1 C2 1.406(2)
C1 C6 1.407(2)
C2 C3 1.369(2)
C2 H2 1.06(2)
C3 C4 1.400(3)
C3 H3 1.01(2)
C4 C5 1.386(2)
C4 H4 1.03(2)
C5 C6 1.399(2)
C5 H5 0.93(1)
C6 C7 1.441(2)
C7 C8 1.362(2)
C7 C9 1.508(2)
C8 H8 1.06(2)
C9 C10 1.537(2)
C9 C14 1.550(2)
C9 H9 1.02(1)
C10 C11 1.522(2)
C10 H10a 1.01(1)
C10 H10b 1.01(2)
C11 C12 1.517(2)
C11 H11a 1.00(1)
C11 H11b 1.03(2)
C12 C13 1.526(2)
C12 H12a 0.96(1)
C12 H12b 0.99(2)
C13 C14 1.532(2)
C13 H13b 0.96(2)
C13 H13a 0.98(2)
C14 C15 1.548(2)
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
C8 N1 C1 C2 -178.8(2)
C8 N1 C1 C6 1.3(2)
C1 N1 C8 C7 -1.5(2)
N1 C1 C2 C3 179.8(2)
C6 C1 C2 C3 -0.3(2)
N1 C1 C6 C5 -179.4(1)
N1 C1 C6 C7 -0.7(1)
C2 C1 C6 C5 0.7(2)
C2 C1 C6 C7 179.4(1)
C1 C2 C3 C4 0.1(3)
C2 C3 C4 C5 -0.3(3)
C3 C4 C5 C6 0.7(2)
C4 C5 C6 C1 -0.9(2)
C4 C5 C6 C7 -179.2(1)
C1 C6 C7 C8 -0.2(1)
C1 C6 C7 C9 -179.6(1)
C5 C6 C7 C8 178.2(1)
C5 C6 C7 C9 -1.2(2)
C6 C7 C8 N1 1.1(2)
C9 C7 C8 N1 -179.5(1)
C6 C7 C9 C10 144.2(1)
C6 C7 C9 C14 -88.7(1)
C8 C7 C9 C10 -35.1(2)
C8 C7 C9 C14 92.0(2)
C7 C9 C10 C11 -177.8(1)
C14 C9 C10 C11 54.4(1)
C7 C9 C14 N2 -58.2(1)
C7 C9 C14 C13 -178.9(1)
C7 C9 C14 C15 58.5(1)
C10 C9 C14 N2 69.2(1)
C10 C9 C14 C13 -51.5(1)
C10 C9 C14 C15 -174.0(1)
C9 C10 C11 C12 -56.6(2)
C10 C11 C12 C13 55.6(2)
C11 C12 C13 C14 -53.9(2)
C12 C13 C14 N2 -69.0(1)
C12 C13 C14 C9 51.8(1)
C12 C13 C14 C15 174.3(1)
N2 C14 C15 O1 -172.8(1)
N2 C14 C15 O2 8.7(1)
C9 C14 C15 O1 68.7(1)
C9 C14 C15 O2 -109.9(1)
C13 C14 C15 O1 -54.4(1)
C13 C14 C15 O2 127.1(1)
