#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/37/2223740.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_2223740
loop_
_publ_author_name
'Yamada, Kazuhiko'
'Hashizume, Daisuke'
'Shimizu, Tadashi'
_publ_section_title
;
 N-(Fluoren-9-ylmethoxycarbonyl)-<small>L</small>-aspartic acid
 4-tert-butyl ester
;
_journal_coeditor_code           FJ2243
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2606
_journal_page_last               o2607
_journal_paper_doi               10.1107/S1600536809037611
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C23 H25 N O6'
_chemical_formula_moiety         'C23 H25 N O6'
_chemical_formula_sum            'C23 H25 N O6'
_chemical_formula_weight         411.44
_chemical_name_systematic
;
N-(Fluoren-9-ylmethoxycarbonyl)-L-aspartic acid
4-tert-butyl ester
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7166(4)
_cell_length_b                   11.1175(10)
_cell_length_c                   32.083(3)
_cell_measurement_reflns_used    15181
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      1.83
_cell_volume                     2039.0(3)
_computing_cell_refinement       'HKL2000 (Otwinowski & Minor, 1997)'
_computing_data_collection
;
CrystalClear (Rigaku/MSC, 2005)
;
_computing_data_reduction        'HKL2000 (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al.,  2005)'
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type
'Rigaku AFC-8 diffractometer with Saturn70 CCD detector'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            15110
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         1.94
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.270
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.129
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0694P)²+0.981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1484
_reflns_number_gt                2167
_reflns_number_total             2722
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fj2243.cif
_cod_data_source_block           I
_cod_database_code               2223740
_cod_database_fobs_code          2223740
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.6301(5) 0.4494(2) 0.15286(8) 0.0271(6) Uani d . 1 . .
O O2 0.7666(5) 0.3298(2) 0.10086(7) 0.0237(6) Uani d . 1 . .
O O3 1.1545(5) 0.4557(2) 0.20322(8) 0.0254(6) Uani d . 1 . .
H H3 1.2064 0.5245 0.2089 0.038 Uiso calc R 1 . .
O O4 0.8720(5) 0.5069(2) 0.24884(8) 0.0267(6) Uani d . 1 . .
O O5 0.6813(5) 0.1857(2) 0.28643(7) 0.0230(6) Uani d . 1 . .
O O6 0.3240(5) 0.2717(2) 0.27449(7) 0.0207(6) Uani d . 1 . .
N N1 0.6108(6) 0.3053(3) 0.22971(9) 0.0221(7) Uani d . 1 . .
H H1 0.5004 0.3395 0.2147 0.027 Uiso calc R 1 . .
C C1 0.8504(7) 0.3115(3) 0.21511(11) 0.0203(8) Uani d . 1 . .
H H1A 0.9431 0.2511 0.2313 0.024 Uiso calc R 1 . .
C C2 0.8711(7) 0.2786(3) 0.16889(11) 0.0221(8) Uani d . 1 . .
H H2A 1.0385 0.2787 0.1610 0.027 Uiso calc R 1 . .
H H2B 0.8106 0.1961 0.1648 0.027 Uiso calc R 1 . .
C C3 0.7406(7) 0.3629(3) 0.14049(11) 0.0205(8) Uani d . 1 . .
C C4 0.9549(7) 0.4366(3) 0.22432(11) 0.0215(8) Uani d . 1 . .
C C5 0.6574(8) 0.4001(3) 0.06656(11) 0.0254(9) Uani d . 1 . .
C C6 0.7397(9) 0.3306(4) 0.02814(12) 0.0363(11) Uani d . 1 . .
H H6A 0.6839 0.2474 0.0298 0.054 Uiso calc R 1 . .
H H6B 0.9110 0.3312 0.0270 0.054 Uiso calc R 1 . .
H H6C 0.6768 0.3687 0.0030 0.054 Uiso calc R 1 . .
C C7 0.7598(8) 0.5265(3) 0.06653(13) 0.0309(9) Uani d . 1 . .
H H7A 0.9308 0.5216 0.0676 0.046 Uiso calc R 1 . .
H H7B 0.7024 0.5706 0.0909 0.046 Uiso calc R 1 . .
H H7C 0.7120 0.5685 0.0411 0.046 Uiso calc R 1 . .
C C8 0.3951(8) 0.3978(4) 0.07039(14) 0.0333(10) Uani d . 1 . .
H H8A 0.3481 0.4396 0.0959 0.050 Uiso calc R 1 . .
H H8B 0.3410 0.3142 0.0715 0.050 Uiso calc R 1 . .
H H8C 0.3253 0.4381 0.0462 0.050 Uiso calc R 1 . .
C C9 0.5502(7) 0.2491(3) 0.26529(11) 0.0180(7) Uani d . 1 . .
C C10 0.2379(7) 0.2366(3) 0.31542(10) 0.0206(8) Uani d . 1 . .
H H10A 0.3663 0.2015 0.3322 0.025 Uiso calc R 1 . .
H H10B 0.1125 0.1758 0.3126 0.025 Uiso calc R 1 . .
C C11 0.1424(7) 0.3503(3) 0.33673(11) 0.0199(8) Uani d . 1 . .
H H11 0.0232 0.3901 0.3185 0.024 Uiso calc R 1 . .
C C12 0.0379(7) 0.3219(3) 0.37912(11) 0.0231(8) Uani d . 1 . .
C C13 -0.1547(8) 0.2505(3) 0.38905(11) 0.0243(8) Uani d . 1 . .
H H13 -0.2397 0.2099 0.3679 0.029 Uiso calc R 1 . .
C C14 -0.2195(7) 0.2401(3) 0.43060(12) 0.0263(9) Uani d . 1 . .
H H14 -0.3507 0.1918 0.4378 0.032 Uiso calc R 1 . .
C C15 -0.0960(8) 0.2990(3) 0.46202(12) 0.0284(9) Uani d . 1 . .
H H15 -0.1433 0.2903 0.4902 0.034 Uiso calc R 1 . .
C C16 0.0969(7) 0.3707(3) 0.45224(12) 0.0261(9) Uani d . 1 . .
H H16 0.1830 0.4103 0.4735 0.031 Uiso calc R 1 . .
C C17 0.1598(8) 0.3825(3) 0.41070(11) 0.0227(8) Uani d . 1 . .
C C18 0.3500(7) 0.4533(3) 0.39111(11) 0.0220(8) Uani d . 1 . .
C C19 0.5228(8) 0.5253(3) 0.40880(12) 0.0286(9) Uani d . 1 . .
H H19 0.5306 0.5365 0.4381 0.034 Uiso calc R 1 . .
C C20 0.6843(8) 0.5807(3) 0.38242(13) 0.0302(10) Uani d . 1 . .
H H20 0.8067 0.6279 0.3940 0.036 Uiso calc R 1 . .
C C21 0.6685(8) 0.5678(3) 0.33946(13) 0.0289(9) Uani d . 1 . .
H H21 0.7788 0.6072 0.3220 0.035 Uiso calc R 1 . .
C C22 0.4919(8) 0.4973(3) 0.32146(12) 0.0250(8) Uani d . 1 . .
H H22 0.4792 0.4901 0.2920 0.030 Uiso calc R 1 . .
C C23 0.3357(7) 0.4382(3) 0.34766(11) 0.0230(8) Uani d . 1 . .
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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C3 O2 C5 . . 120.9(3) no
C4 O3 H3 . . 109.5 no
C9 O6 C10 . . 118.1(3) no
C9 N1 C1 . . 122.6(3) no
C9 N1 H1 . . 118.7 no
C1 N1 H1 . . 118.7 no
N1 C1 C2 . . 112.0(3) no
N1 C1 C4 . . 110.3(3) no
C2 C1 C4 . . 111.7(3) no
N1 C1 H1A . . 107.5 no
C2 C1 H1A . . 107.5 no
C4 C1 H1A . . 107.5 no
C3 C2 C1 . . 113.6(3) no
C3 C2 H2A . . 108.9 no
C1 C2 H2A . . 108.9 no
C3 C2 H2B . . 108.9 no
C1 C2 H2B . . 108.9 no
H2A C2 H2B . . 107.7 no
O1 C3 O2 . . 126.0(3) no
O1 C3 C2 . . 123.5(3) no
O2 C3 C2 . . 110.5(3) no
O4 C4 O3 . . 124.1(3) no
O4 C4 C1 . . 123.8(4) no
O3 C4 C1 . . 112.0(3) no
O2 C5 C8 . . 110.4(3) no
O2 C5 C7 . . 108.9(3) no
C8 C5 C7 . . 113.5(4) no
O2 C5 C6 . . 101.6(3) no
C8 C5 C6 . . 111.3(4) no
C7 C5 C6 . . 110.3(3) no
C5 C6 H6A . . 109.5 no
C5 C6 H6B . . 109.5 no
H6A C6 H6B . . 109.5 no
C5 C6 H6C . . 109.5 no
H6A C6 H6C . . 109.5 no
H6B C6 H6C . . 109.5 no
C5 C7 H7A . . 109.5 no
C5 C7 H7B . . 109.5 no
H7A C7 H7B . . 109.5 no
C5 C7 H7C . . 109.5 no
H7A C7 H7C . . 109.5 no
H7B C7 H7C . . 109.5 no
C5 C8 H8A . . 109.5 no
C5 C8 H8B . . 109.5 no
H8A C8 H8B . . 109.5 no
C5 C8 H8C . . 109.5 no
H8A C8 H8C . . 109.5 no
H8B C8 H8C . . 109.5 no
O5 C9 N1 . . 125.1(4) no
O5 C9 O6 . . 124.7(3) no
N1 C9 O6 . . 110.2(3) no
O6 C10 C11 . . 107.5(3) no
O6 C10 H10A . . 110.2 no
C11 C10 H10A . . 110.2 no
O6 C10 H10B . . 110.2 no
C11 C10 H10B . . 110.2 no
H10A C10 H10B . . 108.5 no
C23 C11 C12 . . 102.3(3) no
C23 C11 C10 . . 112.0(3) no
C12 C11 C10 . . 111.5(3) no
C23 C11 H11 . . 110.3 no
C12 C11 H11 . . 110.3 no
C10 C11 H11 . . 110.3 no
C13 C12 C17 . . 120.1(3) no
C13 C12 C11 . . 129.3(3) no
C17 C12 C11 . . 110.6(3) no
C14 C13 C12 . . 118.5(4) no
C14 C13 H13 . . 120.7 no
C12 C13 H13 . . 120.7 no
C13 C14 C15 . . 121.3(4) no
C13 C14 H14 . . 119.3 no
C15 C14 H14 . . 119.3 no
C14 C15 C16 . . 120.4(4) no
C14 C15 H15 . . 119.8 no
C16 C15 H15 . . 119.8 no
C17 C16 C15 . . 118.4(4) no
C17 C16 H16 . . 120.8 no
C15 C16 H16 . . 120.8 no
C16 C17 C12 . . 121.3(4) no
C16 C17 C18 . . 130.4(4) no
C12 C17 C18 . . 108.3(3) no
C19 C18 C23 . . 120.9(4) no
C19 C18 C17 . . 130.8(3) no
C23 C18 C17 . . 108.3(3) no
C18 C19 C20 . . 118.4(4) no
C18 C19 H19 . . 120.8 no
C20 C19 H19 . . 120.8 no
C21 C20 C19 . . 120.9(4) no
C21 C20 H20 . . 119.6 no
C19 C20 H20 . . 119.6 no
C20 C21 C22 . . 120.9(4) no
C20 C21 H21 . . 119.6 no
C22 C21 H21 . . 119.6 no
C23 C22 C21 . . 118.5(4) no
C23 C22 H22 . . 120.7 no
C21 C22 H22 . . 120.7 no
C22 C23 C18 . . 120.3(4) no
C22 C23 C11 . . 129.2(3) no
C18 C23 C11 . . 110.4(3) no
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
O1 C3 . 1.218(4) no
O2 C3 . 1.332(4) no
O2 C5 . 1.487(4) no
O3 C4 . 1.344(5) no
O3 H3 . 0.8400 no
O4 C4 . 1.206(4) no
O5 C9 . 1.232(4) no
O6 C9 . 1.350(5) no
O6 C10 . 1.456(4) no
N1 C9 . 1.346(4) no
N1 C1 . 1.450(5) no
N1 H1 . 0.8800 no
C1 C2 . 1.532(5) no
C1 C4 . 1.542(5) no
C1 H1A . 1.0000 no
C2 C3 . 1.504(5) no
C2 H2A . 0.9900 no
C2 H2B . 0.9900 no
C5 C8 . 1.504(6) no
C5 C7 . 1.522(5) no
C5 C6 . 1.529(5) no
C6 H6A . 0.9800 no
C6 H6B . 0.9800 no
C6 H6C . 0.9800 no
C7 H7A . 0.9800 no
C7 H7B . 0.9800 no
C7 H7C . 0.9800 no
C8 H8A . 0.9800 no
C8 H8B . 0.9800 no
C8 H8C . 0.9800 no
C10 C11 . 1.537(5) no
C10 H10A . 0.9900 no
C10 H10B . 0.9900 no
C11 C23 . 1.516(5) no
C11 C12 . 1.518(5) no
C11 H11 . 1.0000 no
C12 C13 . 1.395(6) no
C12 C17 . 1.402(5) no
C13 C14 . 1.388(5) no
C13 H13 . 0.9500 no
C14 C15 . 1.394(6) no
C14 H14 . 0.9500 no
C15 C16 . 1.397(6) no
C15 H15 . 0.9500 no
C16 C17 . 1.387(5) no
C16 H16 . 0.9500 no
C17 C18 . 1.482(5) no
C18 C19 . 1.392(5) no
C18 C23 . 1.407(5) no
C19 C20 . 1.395(6) no
C19 H19 . 0.9500 no
C20 C21 . 1.389(6) no
C20 H20 . 0.9500 no
C21 C22 . 1.402(6) no
C21 H21 . 0.9500 no
C22 C23 . 1.392(5) no
C22 H22 . 0.9500 no
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
O3 H3 O5 3_755 0.84 1.91 2.744(3) 171.7
N1 H1 O3 1_455 0.88 2.39 3.213(4) 155.7
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C9 N1 C1 C2 . . . . 132.6(3) no
C9 N1 C1 C4 . . . . -102.3(4) no
N1 C1 C2 C3 . . . . 62.5(4) no
C4 C1 C2 C3 . . . . -61.9(4) no
C5 O2 C3 O1 . . . . 0.3(6) no
C5 O2 C3 C2 . . . . -179.0(3) no
C1 C2 C3 O1 . . . . 0.5(5) no
C1 C2 C3 O2 . . . . 179.7(3) no
N1 C1 C4 O4 . . . . 17.0(5) no
C2 C1 C4 O4 . . . . 142.3(4) no
N1 C1 C4 O3 . . . . -165.8(3) no
C2 C1 C4 O3 . . . . -40.5(4) no
C3 O2 C5 C8 . . . . -63.1(4) no
C3 O2 C5 C7 . . . . 62.2(5) no
C3 O2 C5 C6 . . . . 178.7(3) no
C1 N1 C9 O5 . . . . -9.2(5) no
C1 N1 C9 O6 . . . . 171.1(3) no
C10 O6 C9 O5 . . . . 10.9(5) no
C10 O6 C9 N1 . . . . -169.3(3) no
C9 O6 C10 C11 . . . . 122.3(3) no
O6 C10 C11 C23 . . . . -68.6(4) no
O6 C10 C11 C12 . . . . 177.4(3) no
C23 C11 C12 C13 . . . . 176.5(4) no
C10 C11 C12 C13 . . . . -63.7(5) no
C23 C11 C12 C17 . . . . -1.7(4) no
C10 C11 C12 C17 . . . . 118.1(4) no
C17 C12 C13 C14 . . . . -0.8(5) no
C11 C12 C13 C14 . . . . -178.8(4) no
C12 C13 C14 C15 . . . . -0.2(6) no
C13 C14 C15 C16 . . . . 0.2(6) no
C14 C15 C16 C17 . . . . 0.7(6) no
C15 C16 C17 C12 . . . . -1.6(6) no
C15 C16 C17 C18 . . . . 178.6(4) no
C13 C12 C17 C16 . . . . 1.7(6) no
C11 C12 C17 C16 . . . . -179.9(4) no
C13 C12 C17 C18 . . . . -178.5(3) no
C11 C12 C17 C18 . . . . -0.1(4) no
C16 C17 C18 C19 . . . . 1.9(7) no
C12 C17 C18 C19 . . . . -177.9(4) no
C16 C17 C18 C23 . . . . -178.1(4) no
C12 C17 C18 C23 . . . . 2.1(4) no
C23 C18 C19 C20 . . . . -1.0(6) no
C17 C18 C19 C20 . . . . 178.9(4) no
C18 C19 C20 C21 . . . . 2.2(6) no
C19 C20 C21 C22 . . . . -1.0(6) no
C20 C21 C22 C23 . . . . -1.5(6) no
C21 C22 C23 C18 . . . . 2.6(6) no
C21 C22 C23 C11 . . . . -175.1(4) no
C19 C18 C23 C22 . . . . -1.4(6) no
C17 C18 C23 C22 . . . . 178.7(3) no
C19 C18 C23 C11 . . . . 176.7(3) no
C17 C18 C23 C11 . . . . -3.2(4) no
C12 C11 C23 C22 . . . . -179.1(4) no
C10 C11 C23 C22 . . . . 61.3(5) no
C12 C11 C23 C18 . . . . 3.0(4) no
C10 C11 C23 C18 . . . . -116.5(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2006762
