#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/62/2236239.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_2236239
loop_
_publ_author_name
'Tiritiris, Ioannis'
_publ_section_title
;
 Piperidine-1-carboximidamide
;
_journal_coeditor_code           GO2073
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3253
_journal_paper_doi               10.1107/S1600536812044467
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C6 H13 N3'
_chemical_formula_moiety         'C6 H13 N3'
_chemical_formula_sum            'C6 H13 N3'
_chemical_formula_weight         127.19
_chemical_melting_point          409
_chemical_name_systematic
;
Piperidine-1-carboximidamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.887(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.2193(9)
_cell_length_b                   5.5784(5)
_cell_length_c                   10.4885(7)
_cell_measurement_reflns_used    4190
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      73.45
_cell_measurement_theta_min      3.62
_cell_volume                     714.55(10)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Kappa APEXII DUO'
_diffrn_measurement_method       'φ scans, and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0546
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4190
_diffrn_reflns_theta_full        73.45
_diffrn_reflns_theta_max         73.45
_diffrn_reflns_theta_min         3.62
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.213
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1413
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0445
_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)+(0.0625P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1037
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                1116
_reflns_number_total             1413
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            go2073.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236239
_cod_database_fobs_code          2236239
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+z
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_symmetry_multiplicity
C C1 0.38570(11) 0.2272(2) 0.20721(12) 0.0194(3) Uani d . 1 1
N N1 0.41982(10) 0.26476(18) 0.32513(11) 0.0229(3) Uani d . 1 1
H H11 0.4665(14) 0.393(3) 0.3256(16) 0.031(4) Uiso d . 1 1
N N2 0.40843(11) 0.37432(19) 0.10763(12) 0.0248(3) Uani d . 1 1
H H21 0.4040(14) 0.315(3) 0.0240(18) 0.037(4) Uiso d . 1 1
H H22 0.4598(14) 0.497(3) 0.1251(15) 0.035(4) Uiso d . 1 1
N N3 0.32466(10) 0.02529(17) 0.17918(10) 0.0225(3) Uani d . 1 1
C C2 0.25890(12) -0.0007(2) 0.06138(13) 0.0270(4) Uani d . 1 1
H H2A 0.2591 -0.1706 0.0341 0.032 Uiso calc R 1 1
H H2B 0.2915 0.0964 -0.0067 0.032 Uiso calc R 1 1
C C3 0.14128(12) 0.0807(2) 0.08029(14) 0.0279(4) Uani d . 1 1
H H3A 0.1403 0.2540 0.1006 0.034 Uiso calc R 1 1
H H3B 0.0972 0.0553 0.0005 0.034 Uiso calc R 1 1
C C4 0.09150(13) -0.0602(2) 0.18847(14) 0.0275(3) Uani d . 1 1
H H4A 0.0179 0.0040 0.2054 0.033 Uiso calc R 1 1
H H4B 0.0833 -0.2304 0.1631 0.033 Uiso calc R 1 1
C C5 0.16364(12) -0.0434(2) 0.30906(14) 0.0273(4) Uani d . 1 1
H H5A 0.1341 -0.1493 0.3754 0.033 Uiso calc R 1 1
H H5B 0.1629 0.1231 0.3416 0.033 Uiso calc R 1 1
C C6 0.28172(12) -0.1171(2) 0.28289(13) 0.0246(3) Uani d . 1 1
H H6A 0.3282 -0.0937 0.3610 0.030 Uiso calc R 1 1
H H6B 0.2837 -0.2892 0.2600 0.030 Uiso calc R 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 0.0181 0.0091 '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 0.0311 0.0180 '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
N1 C1 N2 124.09(11)
N1 C1 N3 119.08(11)
N2 C1 N3 116.82(12)
C1 N1 H11 108.1(11)
C1 N2 H21 119.8(10)
C1 N2 H22 116.1(10)
H21 N2 H22 117.2(14)
C1 N3 C6 119.46(11)
C1 N3 C2 122.78(10)
C6 N3 C2 112.09(10)
N3 C2 C3 110.80(11)
N3 C2 H2A 109.5
C3 C2 H2A 109.5
N3 C2 H2B 109.5
C3 C2 H2B 109.5
H2A C2 H2B 108.1
C4 C3 C2 110.12(11)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.2
C5 C4 C3 110.67(12)
C5 C4 H4A 109.5
C3 C4 H4A 109.5
C5 C4 H4B 109.5
C3 C4 H4B 109.5
H4A C4 H4B 108.1
C4 C5 C6 110.95(12)
C4 C5 H5A 109.4
C6 C5 H5A 109.4
C4 C5 H5B 109.4
C6 C5 H5B 109.4
H5A C5 H5B 108.0
N3 C6 C5 110.55(11)
N3 C6 H6A 109.5
C5 C6 H6A 109.5
N3 C6 H6B 109.5
C5 C6 H6B 109.5
H6A C6 H6B 108.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3090(17)
C1 N2 1.3640(17)
C1 N3 1.3773(16)
N1 H11 0.913(17)
N2 H21 0.937(18)
N2 H22 0.943(17)
N3 C6 1.4585(17)
N3 C2 1.4587(17)
C2 C3 1.526(2)
C2 H2A 0.9900
C2 H2B 0.9900
C3 C4 1.5235(19)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.521(2)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.534(2)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
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
N2 H21 N1 4_554 0.94(2) 2.15(2) 3.0710(10) 168.0(10) y
N2 H22 N1 2_655 0.94(2) 2.15(2) 3.0900(10) 177.0(10) y
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
N1 C1 N3 C6 11.63(18)
N2 C1 N3 C6 -169.57(11)
N1 C1 N3 C2 162.94(12)
N2 C1 N3 C2 -18.25(18)
C1 N3 C2 C3 -93.09(14)
C6 N3 C2 C3 60.10(13)
N3 C2 C3 C4 -56.89(14)
C2 C3 C4 C5 53.91(15)
C3 C4 C5 C6 -53.30(14)
C1 N3 C6 C5 95.35(14)
C2 N3 C6 C5 -58.83(14)
C4 C5 C6 N3 55.17(13)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 177636
