#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/33/01/4330185.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_4330185
loop_
_publ_author_name
'Evgeny V. Tretyakov'
'Svyatoslav E. Tolstikov'
'Anastasiya O. Suvorova'
'Aleksey V. Polushkin'
'Galina V. Romanenko'
'Artem S. Bogomyakov'
'Sergey L. Veber'
'Matvey V. Fedin'
'Dmitry V. Stass'
'Edward Reijerse'
'Wolfgang Lubitz'
'Ekaterina M. Zueva'
'Victor I. Ovcharenko'
_publ_section_title
;
 Crucial Role of Paramagnetic Ligands for Magnetostructural Anomalies in
 "Breathing Crystals"
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9385
_journal_page_last               9394
_journal_paper_doi               10.1021/ic301149e
_journal_volume                  51
_journal_year                    2012
_chemical_formula_sum            'C8 H15 N3 O'
_chemical_formula_weight         169.23
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 99.277(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.7677(6)
_cell_length_b                   12.4619(10)
_cell_length_c                   11.9232(11)
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      21.34
_cell_measurement_theta_min      2.38
_cell_volume                     992.43(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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      240(2)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0787
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8404
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.38
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.2894
_exptl_absorpt_correction_T_min  0.2559
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       cube
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_hydrogen_treatment    nonconstr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2382
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.820
_refine_ls_R_factor_all          0.1141
_refine_ls_R_factor_gt           0.0426
_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)+(0.0511P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.1043
_reflns_number_gt                1050
_reflns_number_total             2382
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic301149e_si_002_01.cif
_cod_data_source_block           442s
_cod_database_code               4330185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.00694(16) 0.88572(8) 0.65289(8) 0.0466(3) Uani 1 1 d
N1 N -0.01027(18) 0.95566(9) 0.74884(10) 0.0376(4) Uani 1 1 d
C1 C -0.2283(2) 0.96328(12) 0.75756(14) 0.0436(4) Uani 1 1 d
C2 C 0.0822(2) 1.05466(11) 0.72588(12) 0.0351(4) Uani 1 1 d
N2 N 0.26663(19) 1.20597(10) 0.75718(11) 0.0456(4) Uani 1 1 d
N3 N 0.20021(19) 1.19294(10) 0.64522(11) 0.0431(4) Uani 1 1 d
C3 C 0.1948(2) 1.12055(12) 0.80543(16) 0.0436(4) Uani 1 1 d
H3 H 0.224(2) 1.1142(11) 0.8871(14) 0.051(5) Uiso 1 1 d
C4 C 0.2526(5) 1.26900(18) 0.5627(2) 0.0668(6) Uani 1 1 d
H43 H 0.293(3) 1.3379(17) 0.5998(16) 0.095(7) Uiso 1 1 d
H42 H 0.375(4) 1.2420(18) 0.536(2) 0.153(12) Uiso 1 1 d
H41 H 0.150(4) 1.2868(19) 0.510(2) 0.143(12) Uiso 1 1 d
C5 C 0.0887(2) 1.10363(12) 0.62363(16) 0.0415(4) Uani 1 1 d
H5 H 0.036(2) 1.0841(10) 0.5468(13) 0.048(5) Uiso 1 1 d
C11 C -0.3548(3) 1.0053(2) 0.64958(19) 0.0646(6) Uani 1 1 d
H113 H -0.495(3) 1.0048(14) 0.6547(14) 0.080(7) Uiso 1 1 d
H112 H -0.346(3) 0.9557(16) 0.5837(17) 0.094(7) Uiso 1 1 d
H111 H -0.315(3) 1.0837(17) 0.6319(17) 0.113(8) Uiso 1 1 d
C12 C -0.2967(4) 0.85146(18) 0.7854(3) 0.0712(7) Uani 1 1 d
H123 H -0.288(3) 0.8065(16) 0.7254(16) 0.089(8) Uiso 1 1 d
H122 H -0.449(3) 0.8547(14) 0.7940(15) 0.095(7) Uiso 1 1 d
H121 H -0.220(3) 0.8245(14) 0.8583(17) 0.081(7) Uiso 1 1 d
C13 C -0.2448(4) 1.03759(18) 0.85651(19) 0.0579(5) Uani 1 1 d
H133 H -0.210(3) 1.1125(14) 0.8396(15) 0.072(6) Uiso 1 1 d
H131 H -0.158(3) 1.0111(14) 0.9224(16) 0.076(6) Uiso 1 1 d
H132 H -0.385(3) 1.0351(13) 0.8708(14) 0.077(6) Uiso 1 1 d
H1 H 0.085(3) 0.8236(17) 0.6908(16) 0.099(7) Uiso 1 1 d
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
N1 O1 H1 102.2(11)
C2 N1 O1 105.84(10)
C2 N1 C1 115.13(11)
O1 N1 C1 107.24(10)
N1 C1 C13 106.81(14)
N1 C1 C11 112.94(15)
C13 C1 C11 110.23(17)
N1 C1 C12 107.14(14)
C13 C1 C12 109.02(18)
C11 C1 C12 110.54(18)
C5 C2 C3 104.58(15)
C5 C2 N1 129.24(14)
C3 C2 N1 126.12(14)
C3 N2 N3 104.11(12)
C5 N3 N2 112.09(12)
C5 N3 C4 126.97(15)
N2 N3 C4 120.93(15)
N2 C3 C2 112.01(16)
N2 C3 H3 118.0(9)
C2 C3 H3 130.0(9)
N3 C4 H43 110.2(12)
N3 C4 H42 107.7(14)
H43 C4 H42 104.7(18)
N3 C4 H41 113.4(18)
H43 C4 H41 103.5(19)
H42 C4 H41 117(2)
N3 C5 C2 107.20(15)
N3 C5 H5 120.2(9)
C2 C5 H5 132.6(8)
C1 C11 H113 111.8(10)
C1 C11 H112 110.6(11)
H113 C11 H112 103.2(15)
C1 C11 H111 111.4(12)
H113 C11 H111 108.2(16)
H112 C11 H111 111.5(16)
C1 C12 H123 109.2(13)
C1 C12 H122 108.9(10)
H123 C12 H122 106.6(16)
C1 C12 H121 111.4(11)
H123 C12 H121 112.7(18)
H122 C12 H121 107.9(15)
C1 C13 H133 111.5(10)
C1 C13 H131 108.2(11)
H133 C13 H131 110.8(16)
C1 C13 H132 107.8(10)
H133 C13 H132 109.3(14)
H131 C13 H132 109.0(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 N1 1.4577(14)
O1 H1 1.00(2)
N1 C2 1.4296(18)
N1 C1 1.4987(19)
C1 C13 1.518(2)
C1 C11 1.520(2)
C1 C12 1.522(2)
C2 C5 1.370(2)
C2 C3 1.386(2)
N2 C3 1.3380(19)
N2 N3 1.3479(16)
N3 C5 1.3459(18)
N3 C4 1.451(2)
C3 H3 0.965(15)
C4 H43 0.98(2)
C4 H42 0.99(3)
C4 H41 0.89(3)
C5 H5 0.959(15)
C11 H113 0.962(19)
C11 H112 1.01(2)
C11 H111 1.04(2)
C12 H123 0.918(19)
C12 H122 1.05(2)
C12 H121 0.995(19)
C13 H133 0.991(17)
C13 H131 0.961(18)
C13 H132 0.991(19)
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
O1 H1 N2 1.00(2) 1.83(2) 2.8260(16) 173.1(16) 2_546
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661241
