#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/09/2010917.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_2010917
loop_
_publ_author_name
'Buñuel, Elena'
'Cativiela, Carlos'
'Díaz-de-Villegas, María D.'
'Gálvez, José A.'
_publ_section_title
;
 Two new conformationally restricted 4,5-dihydroxynorvaline analogues
 with a norbornane skeleton
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              587
_journal_page_last               591
_journal_paper_doi               10.1107/S0108270100001645
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C18 H23 N O5'
_chemical_formula_weight         333.37
_chemical_name_systematic
;
methyl
(1R,2S,3R,4S)-2-benzamido-3-(1,2-dihydroxyethyl)bicyclo[2.2.1]heptane-2-
carboxylate
;
_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                   7.187(5)
_cell_length_b                   11.720(5)
_cell_length_c                   20.258(5)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      12.46
_cell_measurement_theta_min      7.57
_cell_volume                     1706.4(15)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1993)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1989)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71073
_diffrn_reflns_av_R_equivalents  .013
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            3472
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .095
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .36
_exptl_crystal_size_min          .30
_refine_diff_density_max         .164
_refine_diff_density_min         -.113
_refine_ls_extinction_coef       .054(2)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         1748
_refine_ls_R_factor_gt           .029
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0310P)²+0.3022P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .070
_reflns_number_gt                1525
_reflns_number_total             1748
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jz1375.cif
_cod_data_source_block           endoI
_cod_database_code               2010917
_cod_database_fobs_code          2010917
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -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
O1 -.4223(2) .79237(16) .88666(9) .0566(5) Uani d . 1 . . O
O2 -.2728(2) .66717(12) .82224(8) .0491(4) Uani d . 1 . . O
O3 -.3937(2) .84340(16) .73155(8) .0504(4) Uani d . 1 . . O
O4 .0100(3) 1.08672(15) .78474(9) .0553(5) Uani d . 1 . . O
H4O .000(5) 1.143(3) .7567(15) .074(9) Uiso d . 1 . . H
O5 -.2572(3) 1.25889(15) .78843(10) .0526(5) Uani d . 1 . . O
H5O -.359(4) 1.282(3) .7807(14) .063(9) Uiso d . 1 . . H
N -.0940(3) .84494(17) .76384(9) .0345(4) Uani d . 1 . . N
H .020(4) .850(2) .7516(12) .048(7) Uiso d . 1 . . H
C1 .0446(3) .8040(2) .87218(12) .0438(6) Uani d . 1 . . C
H1 .1071 .7391 .8513 .053 Uiso calc R 1 . . H
C2 -.1312(3) .84683(18) .83492(10) .0345(5) Uani d . 1 . . C
C3 -.1556(3) .97147(18) .86306(10) .0364(5) Uani d . 1 . . C
H3 -.2697 .9731 .8895 .044 Uiso calc R 1 . . H
C4 .0109(4) .9823(2) .91031(12) .0503(6) Uani d . 1 . . C
H4 .0472 1.0611 .9202 .060 Uiso calc R 1 . . H
C5 -.0270(5) .9086(2) .97168(12) .0618(8) Uani d . 1 . . C
H5A -.1519 .9211 .9884 .074 Uiso calc R 1 . . H
H5B .0619 .9248 1.0065 .074 Uiso calc R 1 . . H
C6 -.0038(4) .7858(2) .94560(12) .0544(7) Uani d . 1 . . C
H6A -.1181 .7426 .9505 .065 Uiso calc R 1 . . H
H6B .0957 .7464 .9685 .065 Uiso calc R 1 . . H
C7 .1613(3) .9121(2) .87566(14) .0540(7) Uani d . 1 . . C
H7A .1932 .9419 .8324 .065 Uiso calc R 1 . . H
H7B .2726 .9029 .9022 .065 Uiso calc R 1 . . H
C8 -.2964(3) .76988(19) .85022(11) .0396(5) Uani d . 1 . . C
C9 -.4266(4) .5888(2) .82789(15) .0659(8) Uani d . 1 . . C
H9A -.4352 .5619 .8726 .099 Uiso calc R 1 . . H
H9B -.4071 .5253 .7988 .099 Uiso calc R 1 . . H
H9C -.5399 .6270 .8161 .099 Uiso calc R 1 . . H
C10 -.2261(3) .84975(19) .71729(11) .0377(5) Uani d . 1 . . C
C11 -.1621(3) .86560(19) .64807(11) .0400(5) Uani d . 1 . . C
C12 -.0215(4) .9407(2) .63307(12) .0534(7) Uani d . 1 . . C
H12 .0382 .9805 .6666 .064 Uiso calc R 1 . . H
C13 .0316(5) .9570(2) .56801(13) .0644(8) Uani d . 1 . . C
H13 .1257 1.0086 .5580 .077 Uiso calc R 1 . . H
C14 -.0534(5) .8978(3) .51866(13) .0671(8) Uani d . 1 . . C
H14 -.0167 .9085 .4751 .081 Uiso calc R 1 . . H
C15 -.1921(5) .8230(3) .53323(14) .0770(10) Uani d . 1 . . C
H15 -.2492 .7820 .4996 .092 Uiso calc R 1 . . H
C16 -.2484(4) .8077(3) .59764(13) .0648(8) Uani d . 1 . . C
H16 -.3455 .7578 .6071 .078 Uiso calc R 1 . . H
C17 -.1692(3) 1.06546(19) .81111(11) .0387(5) Uani d . 1 . . C
H17 -.2497 1.0385 .7753 .046 Uiso calc R 1 . . H
C18 -.2513(4) 1.17388(18) .83864(13) .0489(6) Uani d . 1 . . C
H18A -.3760 1.1592 .8548 .059 Uiso calc R 1 . . H
H18B -.1762 1.2006 .8753 .059 Uiso calc R 1 . . H
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'
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
_geom_angle_publ_flag
C8 O2 C9 116.2(2) ?
C17 O4 H4O 108(2) ?
C18 O5 H5O 114(2) ?
C10 N C2 124.19(19) ?
C10 N H 118.1(17) ?
C2 N H 117.2(17) ?
C7 C1 C6 101.2(2) yes
C7 C1 C2 101.65(18) yes
C6 C1 C2 109.2(2) yes
C7 C1 H1 114.4 ?
C6 C1 H1 114.4 ?
C2 C1 H1 114.4 ?
N C2 C8 109.48(17) ?
N C2 C1 108.91(18) yes
C8 C2 C1 110.10(17) yes
N C2 C3 112.92(18) yes
C8 C2 C3 112.82(18) yes
C1 C2 C3 102.34(18) yes
C17 C3 C4 114.78(19) yes
C17 C3 C2 115.21(18) yes
C4 C3 C2 102.40(17) yes
C17 C3 H3 108.0 ?
C4 C3 H3 108.0 ?
C2 C3 H3 108.0 ?
C7 C4 C3 102.71(18) yes
C7 C4 C5 101.2(2) yes
C3 C4 C5 108.6(2) yes
C7 C4 H4 114.3 ?
C3 C4 H4 114.3 ?
C5 C4 H4 114.3 ?
C4 C5 C6 103.2(2) yes
C4 C5 H5A 111.1 ?
C6 C5 H5A 111.1 ?
C4 C5 H5B 111.1 ?
C6 C5 H5B 111.1 ?
H5A C5 H5B 109.1 ?
C5 C6 C1 103.1(2) yes
C5 C6 H6A 111.2 ?
C1 C6 H6A 111.2 ?
C5 C6 H6B 111.2 ?
C1 C6 H6B 111.2 ?
H6A C6 H6B 109.1 ?
C1 C7 C4 94.5(2) ?
C1 C7 H7A 112.8 ?
C4 C7 H7A 112.8 ?
C1 C7 H7B 112.8 ?
C4 C7 H7B 112.8 ?
H7A C7 H7B 110.3 ?
O1 C8 O2 123.6(2) ?
O1 C8 C2 125.8(2) yes
O2 C8 C2 110.29(19) yes
O2 C9 H9A 109.5 ?
O2 C9 H9B 109.5 ?
H9A C9 H9B 109.5 ?
O2 C9 H9C 109.5 ?
H9A C9 H9C 109.5 ?
H9B C9 H9C 109.5 ?
O3 C10 N 121.5(2) ?
O3 C10 C11 121.8(2) ?
N C10 C11 116.71(19) yes
C12 C11 C16 118.9(2) ?
C12 C11 C10 121.1(2) ?
C16 C11 C10 120.0(2) ?
C11 C12 C13 120.1(2) ?
C11 C12 H12 120.0 ?
C13 C12 H12 120.0 ?
C14 C13 C12 120.3(3) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C15 C14 C13 119.9(3) ?
C15 C14 H14 120.1 ?
C13 C14 H14 120.1 ?
C14 C15 C16 120.3(3) ?
C14 C15 H15 119.8 ?
C16 C15 H15 119.8 ?
C11 C16 C15 120.5(3) ?
C11 C16 H16 119.8 ?
C15 C16 H16 119.8 ?
O4 C17 C18 110.30(19) yes
O4 C17 C3 109.21(18) yes
C18 C17 C3 112.21(19) yes
O4 C17 H17 108.3 ?
C18 C17 H17 108.3 ?
C3 C17 H17 108.3 ?
O5 C18 C17 109.7(2) yes
O5 C18 H18A 109.7 ?
C17 C18 H18A 109.7 ?
O5 C18 H18B 109.7 ?
C17 C18 H18B 109.7 ?
H18A C18 H18B 108.2 ?
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 C8 . 1.197(3) yes
O2 C8 . 1.341(3) ?
O2 C9 . 1.442(3) ?
O3 C10 . 1.241(3) ?
O4 C17 . 1.416(3) yes
O4 H4O . .87(3) ?
O5 C18 . 1.424(3) yes
O5 H5O . .80(3) ?
N C10 . 1.340(3) ?
N C2 . 1.465(3) yes
N H . .86(3) ?
C1 C7 . 1.521(4) yes
C1 C6 . 1.542(4) yes
C1 C2 . 1.555(3) yes
C1 H1 . .9800 ?
C2 C8 . 1.523(3) yes
C2 C3 . 1.578(3) yes
C3 C17 . 1.527(3) yes
C3 C4 . 1.538(3) yes
C3 H3 . .9800 ?
C4 C7 . 1.529(4) yes
C4 C5 . 1.538(4) yes
C4 H4 . .9800 ?
C5 C6 . 1.542(4) yes
C5 H5A . .9700 ?
C5 H5B . .9700 ?
C6 H6A . .9700 ?
C6 H6B . .9700 ?
C7 H7A . .9700 ?
C7 H7B . .9700 ?
C9 H9A . .9600 ?
C9 H9B . .9600 ?
C9 H9C . .9600 ?
C10 C11 . 1.488(3) ?
C11 C12 . 1.374(3) ?
C11 C16 . 1.375(3) ?
C12 C13 . 1.385(4) ?
C12 H12 . .9300 ?
C13 C14 . 1.361(4) ?
C13 H13 . .9300 ?
C14 C15 . 1.360(4) ?
C14 H14 . .9300 ?
C15 C16 . 1.378(4) ?
C15 H15 . .9300 ?
C16 H16 . .9300 ?
C17 C18 . 1.508(3) yes
C17 H17 . .9800 ?
C18 H18A . .9700 ?
C18 H18B . .9700 ?
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
_geom_hbond_publ_flag
O4 H4O N 4_556 .87(3) 2.50(3) 3.239(3) 143(3) yes
O4 H4O O2 4_556 .87(3) 2.55(3) 3.026(2) 116(3) yes
O5 H5O O3 4_456 .80(3) 1.93(3) 2.728(3) 175(3) yes
N H O5 4_546 .86(3) 2.17(3) 2.917(3) 146(2) yes
O4 H4O O5 . .87(3) 2.39(3) 2.787(3) 109(2) yes
C3 H3 O1 . .98 2.39 2.882(3) 111 yes
C7 H7A O4 . .97 2.36 2.960(3) 120 yes
C12 H12 O4 . .93 2.70 3.524(3) 147.5 ?
C12 H12 O2 4_556 .93 2.77 3.513(3) 137.5 ?
C7 H7B O1 1_655 .97 2.57 3.313(4) 134 yes
C9 H9B O3 4_446 .96 2.64 3.375(3) 133.6 ?
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
C10 N C2 C8 42.8(3)
C10 N C2 C1 163.2(2)
C10 N C2 C3 -83.8(3)
C7 C1 C2 N 83.3(2)
C6 C1 C2 N -170.3(2)
C7 C1 C2 C8 -156.65(19)
C6 C1 C2 C8 -50.2(2)
C7 C1 C2 C3 -36.5(2)
C6 C1 C2 C3 70.0(2)
N C2 C3 C17 9.8(3)
C8 C2 C3 C17 -115.0(2)
C1 C2 C3 C17 126.7(2)
N C2 C3 C4 -115.51(19)
C8 C2 C3 C4 119.7(2)
C1 C2 C3 C4 1.4(2)
C17 C3 C4 C7 -91.6(2)
C2 C3 C4 C7 34.0(2)
C17 C3 C4 C5 161.8(2)
C2 C3 C4 C5 -72.6(2)
C7 C4 C5 C6 -35.3(3)
C3 C4 C5 C6 72.4(3)
C4 C5 C6 C1 .0(3)
C7 C1 C6 C5 35.5(3)
C2 C1 C6 C5 -71.2(3)
C6 C1 C7 C4 -56.2(2)
C2 C1 C7 C4 56.3(2)
C3 C4 C7 C1 -56.0(2)
C5 C4 C7 C1 56.2(2)
C9 O2 C8 O1 11.4(3)
C9 O2 C8 C2 -174.77(19)
N C2 C8 O1 -136.3(2)
C1 C2 C8 O1 104.0(3)
C3 C2 C8 O1 -9.6(3)
N C2 C8 O2 50.1(2)
C1 C2 C8 O2 -69.6(2)
C3 C2 C8 O2 176.72(18)
C2 N C10 O3 -8.2(4)
C2 N C10 C11 170.5(2)
O3 C10 C11 C12 137.0(3)
N C10 C11 C12 -41.7(3)
O3 C10 C11 C16 -40.7(4)
N C10 C11 C16 140.6(2)
C16 C11 C12 C13 -.1(4)
C10 C11 C12 C13 -177.8(3)
C11 C12 C13 C14 -.9(5)
C12 C13 C14 C15 .6(5)
C13 C14 C15 C16 .7(5)
C12 C11 C16 C15 1.3(4)
C10 C11 C16 C15 179.0(3)
C14 C15 C16 C11 -1.6(5)
C4 C3 C17 O4 43.2(3)
C2 C3 C17 O4 -75.4(2)
C4 C3 C17 C18 -79.5(3)
C2 C3 C17 C18 161.9(2)
O4 C17 C18 O5 56.9(3)
C3 C17 C18 O5 178.93(19)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21182535
