#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:32:41 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180399 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/68/7206876.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_7206876
loop_
_publ_author_name
'Stefankiewicz, Artur R.'
'De Cian, André'
'Harrowfield, Jack'
_publ_section_title
;
 Helix-helix interactions -- homochirality and heterochirality
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              7207
_journal_paper_doi               10.1039/c1ce06081c
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C8 H9 N O3'
_chemical_formula_weight         167.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.1980(8)
_cell_length_b                   8.7310(12)
_cell_length_c                   17.664(2)
_cell_measurement_reflns_used    1848
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      0.998
_cell_volume                     1572.8(3)
_computing_cell_refinement       'Denzo (Nonius B.V., 1998)'
_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo (Nonius B.V., 1998)'
_computing_molecular_graphics    'PLATON 98 (Spek, 1998)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       '/p scans'
_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  0.0911
_diffrn_reflns_av_sigmaI/netI    0.1340
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3185
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.31
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1859
_refine_ls_R_factor_gt           0.0773
_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)+(0.0651P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1672
_reflns_number_gt                868
_reflns_number_total             1774
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce06081c.txt
_cod_data_source_block           as7
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               7206876
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'
'-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_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
C1 C 0.4518(3) 0.0936(4) -0.11279(16) 0.0445(9) Uani 1 1 d .
H1A H 0.3700 0.0348 -0.1146 0.067 Uiso 1 1 calc R
H1B H 0.5266 0.0238 -0.1178 0.067 Uiso 1 1 calc R
H1C H 0.4531 0.1679 -0.1544 0.067 Uiso 1 1 calc R
C2 C 0.3755(3) 0.2894(4) -0.03106(16) 0.0344(8) Uani 1 1 d .
C3 C 0.3971(3) 0.3649(4) 0.04277(16) 0.0323(8) Uani 1 1 d .
C4 C 0.5028(3) 0.3245(4) 0.08809(16) 0.0317(8) Uani 1 1 d .
H4 H 0.5592 0.2440 0.0723 0.038 Uiso 1 1 calc .
C5 C 0.5275(3) 0.3984(4) 0.15539(16) 0.0345(8) Uani 1 1 d .
C6 C 0.4451(3) 0.5181(4) 0.17820(16) 0.0353(8) Uani 1 1 d .
C7 C 0.3377(3) 0.5576(4) 0.13391(17) 0.0406(9) Uani 1 1 d .
H7 H 0.2799 0.6363 0.1502 0.049 Uiso 1 1 calc .
C8 C 0.3147(3) 0.4829(4) 0.06617(16) 0.0386(9) Uani 1 1 d .
H8 H 0.2424 0.5122 0.0355 0.046 Uiso 1 1 calc .
N2 N 0.6334(3) 0.3526(4) 0.20285(16) 0.0401(8) Uani 1 1 d .
O1 O 0.29229(19) 0.3234(3) -0.07691(11) 0.0432(7) Uani 1 1 d .
O2 O 0.46030(19) 0.1735(3) -0.04141(10) 0.0409(6) Uani 1 1 d .
O3 O 0.4786(2) 0.5893(3) 0.24374(12) 0.0487(7) Uani 1 1 d .
H3O H 0.4278 0.6635 0.2513 0.073 Uiso 1 1 calc R
H1N H 0.697(3) 0.322(3) 0.1754(14) 0.028(9) Uiso 1 1 d .
H2N H 0.653(3) 0.429(5) 0.2353(19) 0.069(13) Uiso 1 1 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
C1 0.044(2) 0.050(2) 0.040(2) -0.0069(17) -0.0012(14) 0.0003(18)
C2 0.0260(16) 0.037(2) 0.0400(19) 0.0032(16) 0.0061(14) -0.0071(16)
C3 0.0289(17) 0.033(2) 0.0352(17) 0.0033(15) 0.0029(14) -0.0050(15)
C4 0.0282(17) 0.031(2) 0.0358(17) 0.0045(15) 0.0057(12) 0.0020(15)
C5 0.0329(17) 0.039(2) 0.0313(18) 0.0060(16) -0.0007(13) -0.0034(16)
C6 0.0408(19) 0.037(2) 0.0283(18) -0.0005(15) 0.0037(14) -0.0057(17)
C7 0.0410(19) 0.041(2) 0.039(2) 0.0014(16) 0.0035(15) 0.0068(16)
C8 0.0308(17) 0.043(2) 0.042(2) 0.0067(17) -0.0004(14) -0.0001(17)
N2 0.0339(17) 0.050(2) 0.0363(18) -0.0029(16) 0.0027(14) 0.0038(16)
O1 0.0342(12) 0.0520(17) 0.0433(12) 0.0005(11) -0.0069(10) -0.0005(12)
O2 0.0397(13) 0.0442(16) 0.0387(12) -0.0061(11) -0.0040(9) 0.0063(12)
O3 0.0585(16) 0.0499(19) 0.0375(13) -0.0057(12) -0.0059(11) 0.0080(13)
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
O2 C1 H1A 109.5
O2 C1 H1B 109.5
H1A C1 H1B 109.5
O2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O1 C2 O2 123.0(3)
O1 C2 C3 125.9(3)
O2 C2 C3 111.1(3)
C4 C3 C8 119.1(3)
C4 C3 C2 120.7(3)
C8 C3 C2 120.1(3)
C5 C4 C3 121.4(3)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 119.3(3)
C4 C5 N2 121.0(3)
C6 C5 N2 119.7(3)
O3 C6 C7 124.4(3)
O3 C6 C5 115.9(3)
C7 C6 C5 119.8(3)
C8 C7 C6 120.2(3)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C8 C3 120.2(3)
C7 C8 H8 119.9
C3 C8 H8 119.9
C5 N2 H1N 109.1(17)
C5 N2 H2N 110(2)
H1N N2 H2N 115(3)
C2 O2 C1 116.4(2)
C6 O3 H3O 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O2 1.444(3)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 O1 1.210(3)
C2 O2 1.344(4)
C2 C3 1.478(4)
C3 C4 1.388(4)
C3 C8 1.392(4)
C4 C5 1.376(4)
C4 H4 0.9500
C5 C6 1.400(4)
C5 N2 1.425(4)
C6 O3 1.358(3)
C6 C7 1.389(4)
C7 C8 1.383(4)
C7 H7 0.9500
C8 H8 0.9500
N2 H1N 0.85(3)
N2 H2N 0.90(4)
O3 H3O 0.8400
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
O1 C2 C3 C4 -174.5(3)
O2 C2 C3 C4 6.3(4)
O1 C2 C3 C8 2.5(5)
O2 C2 C3 C8 -176.6(3)
C8 C3 C4 C5 0.0(4)
C2 C3 C4 C5 177.1(3)
C3 C4 C5 C6 -0.7(5)
C3 C4 C5 N2 177.8(3)
C4 C5 C6 O3 -177.6(3)
N2 C5 C6 O3 3.9(4)
C4 C5 C6 C7 1.9(5)
N2 C5 C6 C7 -176.7(3)
O3 C6 C7 C8 177.1(3)
C5 C6 C7 C8 -2.3(5)
C6 C7 C8 C3 1.6(5)
C4 C3 C8 C7 -0.4(5)
C2 C3 C8 C7 -177.5(3)
O1 C2 O2 C1 2.8(4)
C3 C2 O2 C1 -178.1(2)
