#------------------------------------------------------------------------------
#$Date: 2017-02-04 16:11:35 +0200 (Sat, 04 Feb 2017) $
#$Revision: 191719 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/58/7055836.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_7055836
loop_
_publ_author_name
'Zhang, Zhenfeng'
'Wang, Li'
'Xuan, Xiaopeng'
_publ_section_title
;
 The CN⋯C--X σ-hole interaction acts as a conformational
 lock
;
_journal_issue                   1
_journal_name_full               'New J. Chem.'
_journal_page_first              42
_journal_paper_doi               10.1039/C6NJ02622B
_journal_volume                  41
_journal_year                    2017
_chemical_formula_moiety         'C10 H9 N3 O2'
_chemical_formula_sum            'C10 H9 N3 O2'
_chemical_formula_weight         203.20
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/ccdc.csd.cc1klfxh
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-08-23 deposited with the CCDC.
2016-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.883(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.5944(3)
_cell_length_b                   9.3525(4)
_cell_length_c                   22.972(3)
_cell_measurement_reflns_used    2873
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.4
_cell_measurement_theta_min      2.4
_cell_volume                     983.50(15)
_computing_cell_refinement       'Bruker SAINT(Bruker, 2002)'
_computing_data_collection       'Bruker APEX2(Bruker, 2002)'
_computing_data_reduction        'Bruker SAINT(Bruker, 2002)'
_computing_molecular_graphics    'ORTEP-3 for Windows'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            14740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.442
_diffrn_reflns_theta_min         2.352
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.9860
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2971
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0515
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0661P)²+0.1964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1314
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1796
_reflns_number_total             2971
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6nj02622b3.cif
_cod_data_source_block           s468b_0m
_cod_depositor_comments
'Adding full bibliography for 7055835--7055836.cif.'
_cod_original_cell_volume        983.52(14)
_cod_database_code               7055836
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
N1 N -0.0786(3) 0.30860(13) 0.23096(6) 0.0462(3) Uani 1 1 d . .
H1 H -0.1079 0.3994 0.2303 0.055 Uiso 1 1 calc R U
N2 N 0.0965(3) 0.24660(13) 0.19208(5) 0.0430(3) Uani 1 1 d . .
O2 O 0.3487(3) 0.03237(11) 0.14416(5) 0.0598(4) Uani 1 1 d . .
H2 H 0.2492 0.0722 0.1673 0.090 Uiso 1 1 calc R U
C1 C -0.2028(3) 0.22665(15) 0.26979(6) 0.0412(3) Uani 1 1 d . .
O1 O -0.1773(3) 0.09787(12) 0.27273(5) 0.0590(4) Uani 1 1 d . .
C2 C -0.3753(4) 0.31407(17) 0.31010(7) 0.0523(4) Uani 1 1 d . .
H1A H -0.2533 0.3916 0.3262 0.063 Uiso 1 1 calc R U
H2B H -0.5416 0.3562 0.2875 0.063 Uiso 1 1 calc R U
C4 C 0.2105(3) 0.33042(17) 0.15647(7) 0.0470(4) Uani 1 1 d . .
H4 H 0.1712 0.4279 0.1578 0.056 Uiso 1 1 calc R U
C5 C 0.3992(3) 0.27706(17) 0.11427(6) 0.0439(4) Uani 1 1 d . .
C7 C 0.6365(4) 0.0851(2) 0.06694(7) 0.0578(5) Uani 1 1 d . .
H7 H 0.6760 -0.0119 0.0633 0.069 Uiso 1 1 calc R U
C6 C 0.4597(3) 0.13171(17) 0.10898(6) 0.0450(4) Uani 1 1 d . .
C3 C -0.4773(5) 0.23416(19) 0.35681(9) 0.0717(6) Uani 1 1 d . .
C10 C 0.5229(4) 0.3726(2) 0.07696(8) 0.0603(5) Uani 1 1 d . .
H10 H 0.4857 0.4699 0.0801 0.072 Uiso 1 1 calc R U
C8 C 0.7532(4) 0.1816(2) 0.03068(8) 0.0670(5) Uani 1 1 d . .
H8 H 0.8709 0.1496 0.0024 0.080 Uiso 1 1 calc R U
C9 C 0.6988(4) 0.3252(2) 0.03560(8) 0.0693(6) Uani 1 1 d . .
H9 H 0.7807 0.3900 0.0110 0.083 Uiso 1 1 calc R U
N3 N -0.5613(8) 0.1736(2) 0.39364(12) 0.1612(14) Uani 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
C1 N1 N2 119.70(12)
C1 N1 H1 120.1
N2 N1 H1 120.1
C4 N2 N1 116.76(13)
C6 O2 H2 109.5
O1 C1 N1 124.13(13)
O1 C1 C2 123.89(14)
N1 C1 C2 111.97(13)
C3 C2 C1 113.75(14)
C3 C2 H1A 108.8
C1 C2 H1A 108.8
C3 C2 H2B 108.8
C1 C2 H2B 108.8
H1A C2 H2B 107.7
N2 C4 C5 121.37(14)
N2 C4 H4 119.3
C5 C4 H4 119.3
C10 C5 C6 118.48(15)
C10 C5 C4 119.45(15)
C6 C5 C4 122.07(14)
C8 C7 C6 120.02(17)
C8 C7 H7 120.0
C6 C7 H7 120.0
O2 C6 C7 118.14(15)
O2 C6 C5 121.80(13)
C7 C6 C5 120.06(15)
N3 C3 C2 178.6(2)
C9 C10 C5 120.95(18)
C9 C10 H10 119.5
C5 C10 H10 119.5
C7 C8 C9 120.78(17)
C7 C8 H8 119.6
C9 C8 H8 119.6
C8 C9 C10 119.70(17)
C8 C9 H9 120.1
C10 C9 H9 120.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3400(18)
N1 N2 1.3797(16)
N1 H1 0.8600
N2 C4 1.2770(19)
O2 C6 1.3588(18)
O2 H2 0.8200
C1 O1 1.2114(17)
C1 C2 1.510(2)
C2 C3 1.419(2)
C2 H1A 0.9700
C2 H2B 0.9700
C4 C5 1.443(2)
C4 H4 0.9300
C5 C10 1.392(2)
C5 C6 1.395(2)
C7 C8 1.369(3)
C7 C6 1.384(2)
C7 H7 0.9300
C3 N3 1.114(3)
C10 C9 1.372(2)
C10 H10 0.9300
C8 C9 1.372(3)
C8 H8 0.9300
C9 H9 0.9300
