#------------------------------------------------------------------------------
#$Date: 2019-11-17 15:07:16 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230735 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/61/7156176.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_7156176
loop_
_publ_author_name
'Tong, Feng'
'Linares-Mendez, Iamnica J'
'Han, Yi-Fei'
'Wisner, James A.'
'Wang, Hong-Bo'
_publ_section_title
;
 Readily functionalized AAA-DDD triply hydrogen-bonded motifs.
;
_journal_issue                   16
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2947
_journal_page_last               2954
_journal_paper_doi               10.1039/c8ob00479j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_sum            'C14 H14 N4 O'
_chemical_formula_weight         254.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-11-13 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.574(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.753(2)
_cell_length_b                   14.532(4)
_cell_length_c                   11.144(3)
_cell_measurement_reflns_used    3469
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      3.00
_cell_volume                     1241.5(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7080
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.319
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_meas      1.360
_exptl_crystal_F_000             532
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       0.030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2437
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0348
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0459P)²+0.2178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.1021
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1972
_reflns_number_total             2437
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob00479j2.cif
_cod_data_source_block           wanghb211
_cod_depositor_comments          'Adding full bibliography for 7156176.cif.'
_cod_original_cell_volume        1241.7(6)
_cod_database_code               7156176
_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, y+1/2, -z+1/2'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.08830(13) 0.82432(7) 1.00706(9) 0.0565(3) Uani 1 1 d . .
N1 N 0.28522(16) 0.90477(8) 0.70306(9) 0.0529(3) Uani 1 1 d . .
N2 N 0.36706(14) 1.04657(7) 0.78430(9) 0.0448(3) Uani 1 1 d . .
N3 N 0.44570(15) 1.19144(8) 0.85393(10) 0.0497(3) Uani 1 1 d . .
N4 N 0.13471(15) 0.79867(8) 0.81293(10) 0.0486(3) Uani 1 1 d . .
C1 C 0.45588(18) 1.25308(10) 0.94052(12) 0.0512(3) Uani 1 1 d . .
H1A H 0.5012 1.3104 0.9250 0.061 Uiso 1 1 calc R U
C2 C 0.40404(18) 1.23988(10) 1.05503(13) 0.0522(4) Uani 1 1 d . .
H2A H 0.4164 1.2866 1.1127 0.063 Uiso 1 1 calc R U
C3 C 0.33583(17) 1.15759(10) 1.07901(11) 0.0485(3) Uani 1 1 d . .
H3A H 0.3012 1.1466 1.1541 0.058 Uiso 1 1 calc R U
C4 C 0.31754(15) 1.08826(9) 0.98881(10) 0.0397(3) Uani 1 1 d . .
C5 C 0.37628(16) 1.10779(9) 0.87617(10) 0.0401(3) Uani 1 1 d . .
C6 C 0.24428(16) 1.00214(9) 1.00229(11) 0.0416(3) Uani 1 1 d . .
H6A H 0.2054 0.9865 1.0746 0.050 Uiso 1 1 calc R U
C7 C 0.22986(15) 0.94040(9) 0.90811(10) 0.0390(3) Uani 1 1 d . .
C8 C 0.29563(16) 0.96561(9) 0.79993(10) 0.0412(3) Uani 1 1 d . .
C9 C 0.14643(16) 0.85124(9) 0.91731(11) 0.0431(3) Uani 1 1 d . .
C10 C 0.2081(2) 0.82831(10) 0.71500(12) 0.0545(4) Uani 1 1 d . .
H10A H 0.2008 0.7880 0.6496 0.065 Uiso 1 1 calc R U
C11 C 0.05460(19) 0.70656(10) 0.80921(14) 0.0556(4) Uani 1 1 d . .
H11A H 0.0022 0.6928 0.7266 0.067 Uiso 1 1 calc R U
H11B H -0.0374 0.7064 0.8594 0.067 Uiso 1 1 calc R U
C12 C 0.18577(19) 0.63257(10) 0.85330(13) 0.0545(4) Uani 1 1 d . .
H12A H 0.2795 0.6341 0.8046 0.065 Uiso 1 1 calc R U
H12B H 0.2357 0.6455 0.9366 0.065 Uiso 1 1 calc R U
C13 C 0.1067(2) 0.53778(10) 0.84665(15) 0.0598(4) Uani 1 1 d . .
H13A H 0.0613 0.5238 0.7628 0.072 Uiso 1 1 calc R U
H13B H 0.0096 0.5371 0.8924 0.072 Uiso 1 1 calc R U
C14 C 0.2354(3) 0.46417(12) 0.89565(18) 0.0793(5) Uani 1 1 d . .
H14A H 0.1785 0.4053 0.8893 0.119 Uiso 1 1 calc R U
H14B H 0.3306 0.4635 0.8496 0.119 Uiso 1 1 calc R U
H14C H 0.2789 0.4768 0.9792 0.119 Uiso 1 1 calc R U
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
C10 N1 C8 116.52(11)
C8 N2 C5 117.52(11)
C1 N3 C5 117.16(11)
C10 N4 C9 120.81(12)
C10 N4 C11 119.04(12)
C9 N4 C11 119.99(11)
N3 C1 C2 125.50(13)
C3 C2 C1 118.26(13)
C2 C3 C4 119.38(12)
C6 C4 C3 124.25(11)
C6 C4 C5 117.58(11)
C3 C4 C5 118.18(12)
N2 C5 N3 115.23(11)
N2 C5 C4 123.27(12)
N3 C5 C4 121.50(11)
C7 C6 C4 119.56(11)
C6 C7 C8 118.70(12)
C6 C7 C9 120.89(11)
C8 C7 C9 120.41(11)
N2 C8 N1 116.16(11)
N2 C8 C7 123.35(11)
N1 C8 C7 120.49(12)
O1 C9 N4 121.73(13)
O1 C9 C7 124.32(12)
N4 C9 C7 113.93(11)
N1 C10 N4 127.68(13)
N4 C11 C12 112.14(12)
C13 C12 C11 112.69(12)
C12 C13 C14 112.87(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C9 1.2211(15)
N1 C10 1.2783(18)
N1 C8 1.3884(16)
N2 C8 1.3229(17)
N2 C5 1.3502(16)
N3 C1 1.3104(17)
N3 C5 1.3671(17)
N4 C10 1.3729(18)
N4 C9 1.3834(17)
N4 C11 1.4736(18)
C1 C2 1.4071(19)
C2 C3 1.350(2)
C3 C4 1.4154(18)
C4 C6 1.3918(18)
C4 C5 1.4263(17)
C6 C7 1.3726(18)
C7 C8 1.4251(17)
C7 C9 1.4586(19)
C11 C12 1.511(2)
C12 C13 1.505(2)
C13 C14 1.508(2)
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
C5 N3 C1 C2 1.1(2)
N3 C1 C2 C3 -0.8(2)
C1 C2 C3 C4 -0.5(2)
C2 C3 C4 C6 -177.97(12)
C2 C3 C4 C5 1.42(19)
C8 N2 C5 N3 -177.86(11)
C8 N2 C5 C4 1.75(18)
C1 N3 C5 N2 179.54(11)
C1 N3 C5 C4 -0.07(18)
C6 C4 C5 N2 -1.31(18)
C3 C4 C5 N2 179.26(11)
C6 C4 C5 N3 178.28(11)
C3 C4 C5 N3 -1.16(18)
C3 C4 C6 C7 178.82(11)
C5 C4 C6 C7 -0.58(17)
C4 C6 C7 C8 1.86(17)
C4 C6 C7 C9 -177.14(10)
C5 N2 C8 N1 178.89(11)
C5 N2 C8 C7 -0.35(18)
C10 N1 C8 N2 -176.41(12)
C10 N1 C8 C7 2.86(19)
C6 C7 C8 N2 -1.46(18)
C9 C7 C8 N2 177.55(11)
C6 C7 C8 N1 179.33(11)
C9 C7 C8 N1 -1.66(18)
C10 N4 C9 O1 -176.94(12)
C11 N4 C9 O1 -1.64(19)
C10 N4 C9 C7 4.24(17)
C11 N4 C9 C7 179.53(11)
C6 C7 C9 O1 -1.69(19)
C8 C7 C9 O1 179.33(12)
C6 C7 C9 N4 177.10(11)
C8 C7 C9 N4 -1.88(16)
C8 N1 C10 N4 -0.4(2)
C9 N4 C10 N1 -3.4(2)
C11 N4 C10 N1 -178.75(15)
C10 N4 C11 C12 87.19(16)
C9 N4 C11 C12 -88.18(15)
N4 C11 C12 C13 -178.37(12)
C11 C12 C13 C14 -177.50(13)
