#------------------------------------------------------------------------------
#$Date: 2017-03-02 17:12:34 +0200 (Thu, 02 Mar 2017) $
#$Revision: 192777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/50/4025059.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_4025059
loop_
_publ_author_name
'Robin A. Weatherhead'
'Michael D. Carducci'
'Eugene A. Mash'
_publ_contact_author_address
;
     The University of Arizona
     Department of Chemistry and Biochemistry
     1306 E. University Boulevard
     Tucson, AZ 85721-0041
     USA
;
_publ_contact_author_email       emash@u.arizona.edu
_publ_contact_author_fax         520-621-8407
_publ_contact_author_name        'Professor Eugene A. Mash, Jr.'
_publ_contact_author_phone       520-621-6321
_publ_section_title
;
Synthesis of Conformationally Constrained Diaminodicarboxylic Acid
Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8773
_journal_page_last               8778
_journal_paper_doi               10.1021/jo901892d
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C26 H30 N2 O8'
_chemical_formula_sum            'C26 H30 N2 O8'
_chemical_formula_weight         498.52
_chemical_melting_point          254
_chemical_name_common            'trans 1,4 bis-N-CBZ-1,4-dimethyl ester'
_chemical_name_systematic
; 
trans 1,4-bis-phenoxycarbonylamino-cyclohexane-1,4-dicarboxylic acid dimethyl 
ester 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.7750(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2758(6)
_cell_length_b                   7.1597(4)
_cell_length_c                   16.6143(10)
_cell_measurement_reflns_used    12592
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.73
_cell_measurement_theta_min      2.45
_cell_volume                     1220.91(12)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11978
_diffrn_reflns_theta_full        26.06
_diffrn_reflns_theta_max         26.06
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0.24
_diffrn_standards_interval_count 1818
_diffrn_standards_number         51
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   'SADABS (Bruker 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    riding
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2409
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_gt           0.0393
_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)+(0.0377P)²+0.6656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1621
_reflns_number_total             2409
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            jo901892d_si_002_2.cif
_cod_data_source_block           20
_cod_depositor_comments
;
The following automatic conversions were performed:
data name '_symmetry_space_group_it_number' replaced with
'_space_group_IT_number' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst'.

'_symmetry_space_group_number'
data item was removed -- it should have been renamed to
'_space_group_IT_number' as specified in the replacement file
'/home/antanas/src/cod-tools/trunk/data/replacement-values/replacement_tags.lst',
but the replacement data item was already present in the data block
and had the same value as the '_symmetry_space_group_number' data
item.

Automatic conversion script
Id: cif_correct_tags 4998 2017-03-02 13:24:31Z antanas 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4025059
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'
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
O2 O 0.74802(13) 0.46283(18) -0.08482(8) 0.0198(3) Uani 1 1 d . . .
C2 C 0.73239(19) 0.3424(3) -0.02299(12) 0.0181(4) Uani 1 1 d . . .
C8 C 0.8099(2) 0.8149(3) -0.28202(14) 0.0318(5) Uani 1 1 d . . .
H8A H 0.7733 0.7911 -0.3346 0.038 Uiso 1 1 calc R . .
C9 C 0.8132(2) 0.6746(3) -0.22465(13) 0.0274(5) Uani 1 1 d . . .
H9A H 0.7795 0.5546 -0.2385 0.033 Uiso 1 1 calc R . .
C4 C 0.86482(19) 0.7066(3) -0.14735(12) 0.0221(5) Uani 1 1 d . . .
C3 C 0.8740(2) 0.5538(3) -0.08539(13) 0.0248(5) Uani 1 1 d . . .
H3A H 0.9419 0.4625 -0.0991 0.030 Uiso 1 1 calc R . .
H3B H 0.8975 0.6067 -0.0316 0.030 Uiso 1 1 calc R . .
C5 C 0.9130(2) 0.8835(3) -0.12830(14) 0.0310(5) Uani 1 1 d . . .
H5A H 0.9476 0.9090 -0.0754 0.037 Uiso 1 1 calc R . .
C7 C 0.8595(2) 0.9890(3) -0.26318(15) 0.0341(6) Uani 1 1 d . . .
H7A H 0.8586 1.0847 -0.3028 0.041 Uiso 1 1 calc R . .
C6 C 0.9104(2) 1.0230(3) -0.18655(16) 0.0383(6) Uani 1 1 d . . .
H6A H 0.9442 1.1432 -0.1732 0.046 Uiso 1 1 calc R . .
O3 O 0.56876(13) 0.46024(18) 0.11699(8) 0.0200(3) Uani 1 1 d . . .
O4 O 0.57323(13) 0.18757(18) 0.18342(7) 0.0217(3) Uani 1 1 d . . .
C13 C 0.62229(18) -0.0202(3) 0.04950(11) 0.0169(4) Uani 1 1 d . . .
H13A H 0.7179 -0.0040 0.0563 0.020 Uiso 1 1 calc R . .
H13B H 0.5921 -0.0818 0.0986 0.020 Uiso 1 1 calc R . .
C12 C 0.59081(18) -0.1450(3) -0.02342(11) 0.0169(4) Uani 1 1 d . . .
H12A H 0.6321 -0.2686 -0.0141 0.020 Uiso 1 1 calc R . .
H12B H 0.6287 -0.0890 -0.0715 0.020 Uiso 1 1 calc R . .
C10 C 0.56996(18) 0.2912(3) 0.11680(11) 0.0166(4) Uani 1 1 d . . .
C1 C 0.55746(19) 0.1722(3) 0.04031(11) 0.0159(4) Uani 1 1 d . . .
O1 O 0.81735(13) 0.3009(2) 0.02677(8) 0.0260(4) Uani 1 1 d . . .
N1 N 0.60791(15) 0.2776(2) -0.02647(9) 0.0162(4) Uani 1 1 d . . .
HN H 0.5571 0.2995 -0.0696 0.019 Uiso 1 1 calc R . .
C11 C 0.5603(2) 0.2866(3) 0.25905(11) 0.0245(5) Uani 1 1 d . . .
H11A H 0.5641 0.1970 0.3037 0.037 Uiso 1 1 calc R . .
H11B H 0.4766 0.3523 0.2578 0.037 Uiso 1 1 calc R . .
H11C H 0.6314 0.3770 0.2666 0.037 Uiso 1 1 calc R . .
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'
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
C2 O2 C3 115.40(15) . . ?
O1 C2 O2 124.44(18) . . ?
O1 C2 N1 126.27(18) . . ?
O2 C2 N1 109.29(16) . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8A 119.9 . . ?
C9 C8 H8A 119.9 . . ?
C8 C9 C4 120.9(2) . . ?
C8 C9 H9A 119.5 . . ?
C4 C9 H9A 119.5 . . ?
C9 C4 C5 118.5(2) . . ?
C9 C4 C3 121.58(19) . . ?
C5 C4 C3 119.83(19) . . ?
O2 C3 C4 107.75(16) . . ?
O2 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
O2 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C6 C5 C4 120.1(2) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C6 C7 C8 119.4(2) . . ?
C6 C7 H7A 120.3 . . ?
C8 C7 H7A 120.3 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C10 O4 C11 116.56(15) . . ?
C12 C13 C1 111.85(15) . . ?
C12 C13 H13A 109.2 . . ?
C1 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C1 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C12 C1 112.71(15) . 3_655 ?
C13 C12 H12A 109.1 . . ?
C1 C12 H12A 109.1 3_655 . ?
C13 C12 H12B 109.1 . . ?
C1 C12 H12B 109.1 3_655 . ?
H12A C12 H12B 107.8 . . ?
O3 C10 O4 123.70(18) . . ?
O3 C10 C1 123.95(17) . . ?
O4 C10 C1 112.20(16) . . ?
N1 C1 C10 108.97(15) . . ?
N1 C1 C13 111.82(15) . . ?
C10 C1 C13 113.49(15) . . ?
N1 C1 C12 108.07(15) . 3_655 ?
C10 C1 C12 105.23(15) . 3_655 ?
C13 C1 C12 108.91(15) . 3_655 ?
C2 N1 C1 120.86(15) . . ?
C2 N1 HN 119.6 . . ?
C1 N1 HN 119.6 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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
O2 C2 1.357(2) . ?
O2 C3 1.450(2) . ?
C2 O1 1.210(2) . ?
C2 N1 1.359(2) . ?
C8 C7 1.377(3) . ?
C8 C9 1.384(3) . ?
C8 H8A 0.9500 . ?
C9 C4 1.385(3) . ?
C9 H9A 0.9500 . ?
C4 C5 1.391(3) . ?
C4 C3 1.502(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C5 C6 1.390(3) . ?
C5 H5A 0.9500 . ?
C7 C6 1.374(3) . ?
C7 H7A 0.9500 . ?
C6 H6A 0.9500 . ?
O3 C10 1.211(2) . ?
O4 C10 1.332(2) . ?
O4 C11 1.454(2) . ?
C13 C12 1.527(3) . ?
C13 C1 1.534(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C12 C1 1.548(3) 3_655 ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10 C1 1.530(3) . ?
C1 N1 1.458(2) . ?
C1 C12 1.548(3) 3_655 ?
N1 HN 0.8800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 HN O3 0.88 2.27 2.969(2) 136.3 3_665
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
C3 O2 C2 O1 -4.3(3) . . . . ?
C3 O2 C2 N1 175.73(15) . . . . ?
C7 C8 C9 C4 0.7(3) . . . . ?
C8 C9 C4 C5 0.3(3) . . . . ?
C8 C9 C4 C3 -177.49(19) . . . . ?
C2 O2 C3 C4 -169.26(16) . . . . ?
C9 C4 C3 O2 -49.2(2) . . . . ?
C5 C4 C3 O2 133.03(19) . . . . ?
C9 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 C6 176.9(2) . . . . ?
C9 C8 C7 C6 -1.1(3) . . . . ?
C8 C7 C6 C5 0.4(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C1 C13 C12 C1 -56.9(2) . . . 3_655 ?
C11 O4 C10 O3 6.9(3) . . . . ?
C11 O4 C10 C1 -168.80(16) . . . . ?
O3 C10 C1 N1 27.9(3) . . . . ?
O4 C10 C1 N1 -156.46(15) . . . . ?
O3 C10 C1 C13 153.22(19) . . . . ?
O4 C10 C1 C13 -31.1(2) . . . . ?
O3 C10 C1 C12 -87.8(2) . . . 3_655 ?
O4 C10 C1 C12 87.85(18) . . . 3_655 ?
C12 C13 C1 N1 -64.6(2) . . . . ?
C12 C13 C1 C10 171.62(15) . . . . ?
C12 C13 C1 C12 54.8(2) . . . 3_655 ?
O1 C2 N1 C1 11.1(3) . . . . ?
O2 C2 N1 C1 -169.01(15) . . . . ?
C10 C1 N1 C2 57.8(2) . . . . ?
C13 C1 N1 C2 -68.5(2) . . . . ?
C12 C1 N1 C2 171.61(16) 3_655 . . . ?
