#------------------------------------------------------------------------------
#$Date: 2016-02-21 11:56:54 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176809 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/00/2240032.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_2240032
loop_
_publ_author_name
'Ahmad Wani, Naiem'
'Gupta, Vivek K.'
'Kant, Rajni'
'Aravinda, Subrayashastry'
'Rai, Rajkishor'
_publ_section_title
;
 Conformation and crystal structures of 1-aminocyclohexaneacetic acid
 (β^3,3^Ac₆c) in N-protected derivatives
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              272
_journal_page_last               277
_journal_paper_doi               10.1107/S1600536814020777
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C13 H17 N3 O3'
_chemical_formula_moiety         'C13 H17 N3 O3'
_chemical_formula_sum            'C13 H17 N3 O3'
_chemical_formula_weight         263.30
_chemical_name_common            Pyr-beta-3,3-Ac6c-OH
_chemical_name_systematic
;
2-[1-(Pyrazine-2-amido)cyclohexyl]acetic acid
;
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   difmap
_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            4
_cell_length_a                   8.71350(10)
_cell_length_b                   10.53210(10)
_cell_length_c                   14.3907(2)
_cell_measurement_reflns_used    28796
_cell_measurement_temperature    291
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      3.66
_cell_volume                     1320.66(3)
_computing_cell_refinement
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Oxford Diffraction, 2010)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      291
_diffrn_detector_area_resol_mean 16.1049
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Difraction Xcalibur, Sapphire3 CCD'
_diffrn_measurement_method       'ω 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  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0115
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            68869
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         3.87
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(Crysalis PRO; Oxford Diffraction, 2010)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.262
_refine_ls_abs_structure_details
;
(Flack, 1983): 1585 Friedel pairs
;
_refine_ls_abs_structure_Flack   0.2(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         2878
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.4913P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1056
_reflns_number_gt                2670
_reflns_number_total             2878
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zs2313sup1.cif
_cod_data_source_block           III
_cod_database_code               2240032
_cod_database_fobs_code          2240032
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-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_occupancy
_atom_site_symmetry_multiplicity
H H1 0.902(2) 0.412(2) 1.0592(15) 0.030(5) Uiso d 1 1
H H1B2 1.400(3) 0.435(2) 1.2329(16) 0.041(6) Uiso d 1 1
H H1B5 1.272(3) 0.384(2) 1.4161(18) 0.049(7) Uiso d 1 1
H H1B6 1.183(3) 0.442(2) 1.3342(17) 0.048(6) Uiso d 1 1
H H1B1 1.499(2) 0.380(2) 1.3191(16) 0.033(5) Uiso d 1 1
H H1D2 1.651(3) 0.100(3) 1.200(2) 0.061(7) Uiso d 1 1
H H1N 1.161(2) 0.172(2) 1.2259(16) 0.036(6) Uiso d 1 1
H H1G1 1.481(3) 0.256(2) 1.1391(19) 0.045(6) Uiso d 1 1
H H2 0.709(3) 0.107(2) 0.971(2) 0.051(7) Uiso d 1 1
H H3 0.894(3) -0.021(2) 1.0429(17) 0.047(6) Uiso d 1 1
H H1B4 1.269(3) 0.107(2) 1.3669(17) 0.045(6) Uiso d 1 1
H H1G4 1.401(3) 0.050(3) 1.232(2) 0.061(7) Uiso d 1 1
H H1G2 1.616(3) 0.323(3) 1.173(2) 0.066(8) Uiso d 1 1
H H1B3 1.415(3) 0.192(2) 1.3989(19) 0.046(6) Uiso d 1 1
H H1G3 1.502(3) 0.005(3) 1.3184(19) 0.065(8) Uiso d 1 1
H H1D1 1.667(4) 0.176(3) 1.298(2) 0.071(9) Uiso d 1 1
H H21 0.885(5) 0.352(4) 1.458(3) 0.106(13) Uiso d 1 1
C C1 0.9028(2) 0.3259(2) 1.05370(16) 0.0401(4) Uani d 1 1
N N2 0.7893(2) 0.27249(19) 1.00502(14) 0.0442(4) Uani d 1 1
C C3 0.7875(3) 0.1459(2) 1.00191(15) 0.0433(5) Uani d 1 1
C C4 0.8954(3) 0.0736(2) 1.04730(16) 0.0450(5) Uani d 1 1
N N3 1.0074(2) 0.12584(16) 1.09722(13) 0.0398(4) Uani d 1 1
C C6 1.0105(2) 0.25193(18) 1.10026(14) 0.0343(4) Uani d 1 1
C C0 1.1318(2) 0.31669(18) 1.15876(15) 0.0382(4) Uani d 1 1
O O0' 1.1604(2) 0.42890(15) 1.14626(15) 0.0658(6) Uani d 1 1
N N1 1.19610(18) 0.24153(15) 1.22264(12) 0.0348(4) Uani d 1 1
C C1A 1.2995(2) 0.28157(17) 1.29864(13) 0.0311(4) Uani d 1 1
C C1B 1.2100(2) 0.36660(19) 1.36671(16) 0.0381(4) Uani d 1 1
C C1' 1.0648(2) 0.31013(19) 1.40619(15) 0.0423(5) Uani d 1 1
O O1 1.0357(3) 0.2011(2) 1.4129(3) 0.1197(13) Uani d 1 1
O O2 0.9700(2) 0.39599(18) 1.43574(16) 0.0677(6) Uani d 1 1
C C1B1 1.4369(2) 0.3562(2) 1.26078(16) 0.0394(4) Uani d 1 1
C C1G1 1.5373(3) 0.2777(2) 1.19617(18) 0.0504(5) Uani d 1 1
C C1D 1.5948(3) 0.1582(3) 1.2448(2) 0.0575(6) Uani d 1 1
C C1B2 1.3586(2) 0.15966(19) 1.34564(14) 0.0366(4) Uani d 1 1
C C1G2 1.4634(3) 0.0817(2) 1.28311(18) 0.0483(5) Uani d 1 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 0.0016 '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
N2 C1 C6 121.03(19)
N2 C1 H1 117.5(14)
C6 C1 H1 121.3(14)
C3 N2 C1 116.57(18)
N2 C3 C4 122.0(2)
N2 C3 H2 118.2(16)
C4 C3 H2 119.8(16)
N3 C4 C3 121.9(2)
N3 C4 H3 117.3(15)
C3 C4 H3 120.8(15)
C6 N3 C4 116.44(19)
N3 C6 C1 122.0(2)
N3 C6 C0 118.85(18)
C1 C6 C0 119.08(17)
O0' C0 N1 126.08(19)
O0' C0 C6 119.79(18)
N1 C0 C6 114.12(17)
C0 N1 C1A 126.55(16)
C0 N1 H1N 115.3(17)
C1A N1 H1N 116.8(17)
N1 C1A C1B1 111.06(16)
N1 C1A C1B 109.15(15)
C1B1 C1A C1B 108.90(15)
N1 C1A C1B2 106.91(15)
C1B1 C1A C1B2 108.81(16)
C1B C1A C1B2 112.02(16)
C1' C1B C1A 115.79(16)
C1' C1B H1B5 106.5(16)
C1A C1B H1B5 108.4(17)
C1' C1B H1B6 108.0(15)
C1A C1B H1B6 107.2(15)
H1B5 C1B H1B6 111(2)
O1 C1' O2 121.0(2)
O1 C1' C1B 126.5(2)
O2 C1' C1B 112.51(18)
C1' O2 H21 106(3)
C1G1 C1B1 C1A 112.85(17)
C1G1 C1B1 H1B2 113.6(14)
C1A C1B1 H1B2 109.0(14)
C1G1 C1B1 H1B1 108.9(12)
C1A C1B1 H1B1 104.3(12)
H1B2 C1B1 H1B1 107.7(18)
C1B1 C1G1 C1D 110.9(2)
C1B1 C1G1 H1G1 110.5(15)
C1D C1G1 H1G1 111.0(15)
C1B1 C1G1 H1G2 112.3(19)
C1D C1G1 H1G2 111.1(19)
H1G1 C1G1 H1G2 101(2)
C1G2 C1D C1G1 111.1(2)
C1G2 C1D H1D2 106.1(16)
C1G1 C1D H1D2 111.2(16)
C1G2 C1D H1D1 107.4(17)
C1G1 C1D H1D1 113.3(18)
H1D2 C1D H1D1 107(2)
C1G2 C1B2 C1A 113.00(17)
C1G2 C1B2 H1B4 110.6(13)
C1A C1B2 H1B4 109.3(13)
C1G2 C1B2 H1B3 110.4(15)
C1A C1B2 H1B3 102.9(15)
H1B4 C1B2 H1B3 110(2)
C1D C1G2 C1B2 112.6(2)
C1D C1G2 H1G4 109.7(17)
C1B2 C1G2 H1G4 107.0(16)
C1D C1G2 H1G3 111.0(17)
C1B2 C1G2 H1G3 109.4(16)
H1G4 C1G2 H1G3 107(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N2 1.337(3)
C1 C6 1.391(3)
C1 H1 0.91(2)
N2 C3 1.334(3)
C3 C4 1.375(3)
C3 H2 0.91(3)
C4 N3 1.331(3)
C4 H3 1.00(3)
N3 C6 1.329(3)
C6 C0 1.514(3)
C0 O0' 1.221(2)
C0 N1 1.336(3)
N1 C1A 1.478(2)
N1 H1N 0.79(2)
C1A C1B1 1.532(3)
C1A C1B 1.539(2)
C1A C1B2 1.540(3)
C1B C1' 1.509(3)
C1B H1B5 0.91(3)
C1B H1B6 0.95(3)
C1' O1 1.180(3)
C1' O2 1.297(3)
O2 H21 0.93(5)
C1B1 C1G1 1.521(3)
C1B1 H1B2 0.97(2)
C1B1 H1B1 1.03(2)
C1G1 C1D 1.525(4)
C1G1 H1G1 0.98(3)
C1G1 H1G2 0.90(3)
C1D C1G2 1.505(4)
C1D H1D2 1.01(3)
C1D H1D1 1.00(3)
C1B2 C1G2 1.523(3)
C1B2 H1B4 1.00(2)
C1B2 H1B3 0.97(3)
C1G2 H1G4 0.97(3)
C1G2 H1G3 1.01(3)
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
O2 H21 N2 4_655 0.93(4) 1.86(4) 2.791(3) 177(4) yes
N1 H1N N3 . 0.79(2) 2.34(2) 2.729(2) 111.3(19) yes
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
C6 C1 N2 C3 -1.5(3)
C1 N2 C3 C4 0.8(3)
N2 C3 C4 N3 0.3(4)
C3 C4 N3 C6 -0.6(3)
C4 N3 C6 C1 -0.2(3)
C4 N3 C6 C0 177.82(19)
N2 C1 C6 N3 1.3(3)
N2 C1 C6 C0 -176.68(19)
N3 C6 C0 O0' 162.9(2)
C1 C6 C0 O0' -19.1(3)
N3 C6 C0 N1 -18.5(3)
C1 C6 C0 N1 159.53(19)
O0' C0 N1 C1A 8.4(4)
C6 C0 N1 C1A -170.04(17)
C0 N1 C1A C1B1 -54.6(2)
C0 N1 C1A C1B 65.5(2)
C0 N1 C1A C1B2 -173.2(2)
N1 C1A C1B C1' 55.0(2)
C1B1 C1A C1B C1' 176.42(19)
C1B2 C1A C1B C1' -63.2(2)
C1A C1B C1' O1 23.6(4)
C1A C1B C1' O2 -157.9(2)
N1 C1A C1B1 C1G1 -62.6(2)
C1B C1A C1B1 C1G1 177.20(19)
C1B2 C1A C1B1 C1G1 54.8(2)
C1A C1B1 C1G1 C1D -57.0(3)
C1B1 C1G1 C1D C1G2 55.1(3)
N1 C1A C1B2 C1G2 67.3(2)
C1B1 C1A C1B2 C1G2 -52.7(2)
C1B C1A C1B2 C1G2 -173.13(18)
C1G1 C1D C1G2 C1B2 -53.8(3)
C1A C1B2 C1G2 C1D 53.7(3)
