#------------------------------------------------------------------------------
#$Date: 2025-08-18 23:06:14 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301780 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/18/1551882.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_1551882
loop_
_publ_author_name
'Debdas Ray'
'Justin T. Foy'
'Russell P. Hughes'
'Ivan Aprahamian'
_publ_section_title
;
 A switching cascade of hydrazone-based rotary switches through
 coordination-coupled proton relays
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              757
_journal_page_last               762
_journal_paper_doi               10.1038/nchem.1408
_journal_volume                  4
_journal_year                    2012
_chemical_formula_moiety         'C17 H17 N5 O2'
_chemical_formula_sum            'C17 H17 N5 O2'
_chemical_formula_weight         323.36
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.6240(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1905(2)
_cell_length_b                   14.3672(2)
_cell_length_c                   7.24540(10)
_cell_measurement_reflns_used    6288
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.59
_cell_measurement_theta_min      2.93
_cell_volume                     1570.72(4)
_computing_cell_refinement       'APEX2 (BRUKER, V2010.11-3, 2010)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT (BRUKER, V7.68A, 2010)'
_computing_molecular_graphics
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_publication_material
'SHELXTL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_refinement
'SHELXL (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_computing_structure_solution
'SHELXS (Sheldrick, Acta Cryst. A64 2008, 112-122)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω,and/f 0.5 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            10664
_diffrn_reflns_theta_full        68.86
_diffrn_reflns_theta_max         68.86
_diffrn_reflns_theta_min         2.93
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_correction_T_min  0.7551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2886
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0454P)²+0.4153P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0911
_reflns_number_gt                2510
_reflns_number_total             2886
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            nchem.1408-s2.cif
_cod_data_source_block           ia5511
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1551882
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24888(6) 0.77035(6) 0.12080(12) 0.0284(2) Uani 1 1 d . . .
O2 O 0.37302(6) 0.76996(6) 0.32209(13) 0.0336(2) Uani 1 1 d . . .
N1 N 0.26066(7) 0.94946(7) 0.07769(14) 0.0254(2) Uani 1 1 d . . .
N2 N 0.26293(7) 1.04035(7) 0.03946(15) 0.0270(2) Uani 1 1 d . . .
H2 H 0.3124 1.0721 0.0651 0.032 Uiso 1 1 calc R . .
N5 N 0.42059(7) 1.04621(7) 0.26243(15) 0.0308(3) Uani 1 1 d . . .
N4 N 0.49924(7) 0.92130(7) 0.20481(14) 0.0255(2) Uani 1 1 d . . .
N3 N 0.26994(7) 1.22498(7) 0.00145(15) 0.0298(3) Uani 1 1 d . . .
C4 C 0.15691(9) 0.63984(9) 0.0373(2) 0.0351(3) Uani 1 1 d . . .
H4A H 0.1059 0.6785 0.0587 0.053 Uiso 1 1 calc R . .
H4B H 0.1445 0.5747 0.0653 0.053 Uiso 1 1 calc R . .
H4C H 0.1679 0.6452 -0.0929 0.053 Uiso 1 1 calc R . .
C3 C 0.23707(9) 0.67207(9) 0.16085(19) 0.0327(3) Uani 1 1 d . . .
H3A H 0.2282 0.6634 0.2930 0.039 Uiso 1 1 calc R . .
H3B H 0.2899 0.6361 0.1354 0.039 Uiso 1 1 calc R . .
C2 C 0.32139(8) 0.80974(9) 0.20904(16) 0.0250(3) Uani 1 1 d . . .
C1 C 0.33189(8) 0.90926(8) 0.15798(16) 0.0242(3) Uani 1 1 d . . .
C9 C 0.18644(8) 1.08425(9) -0.04118(17) 0.0260(3) Uani 1 1 d . . .
C14 C 0.19104(8) 1.18331(9) -0.05718(16) 0.0256(3) Uani 1 1 d . . .
C13 C 0.11438(9) 1.23292(9) -0.13042(17) 0.0294(3) Uani 1 1 d . . .
C15 C 0.12198(10) 1.33095(10) -0.13731(19) 0.0355(3) Uani 1 1 d . . .
H15 H 0.0723 1.3678 -0.1831 0.043 Uiso 1 1 calc R . .
C16 C 0.20048(11) 1.37220(9) -0.07826(19) 0.0371(3) Uani 1 1 d . . .
H16 H 0.2062 1.4380 -0.0818 0.044 Uiso 1 1 calc R . .
C5 C 0.41662(8) 0.95707(8) 0.21133(16) 0.0250(3) Uani 1 1 d . . .
C7 C 0.50884(9) 1.06689(9) 0.29287(19) 0.0333(3) Uani 1 1 d . . .
H7 H 0.5325 1.1256 0.3334 0.040 Uiso 1 1 calc R . .
C6 C 0.55777(9) 0.99138(9) 0.25688(18) 0.0305(3) Uani 1 1 d . . .
H6 H 0.6206 0.9879 0.2661 0.037 Uiso 1 1 calc R . .
C8 C 0.52533(9) 0.82908(9) 0.14444(19) 0.0307(3) Uani 1 1 d . . .
H8A H 0.5326 0.7869 0.2514 0.046 Uiso 1 1 calc R . .
H8B H 0.5815 0.8339 0.0907 0.046 Uiso 1 1 calc R . .
H8C H 0.4794 0.8048 0.0508 0.046 Uiso 1 1 calc R . .
C17 C 0.27336(10) 1.31631(9) -0.01165(19) 0.0347(3) Uani 1 1 d . . .
H17 H 0.3283 1.3462 0.0261 0.042 Uiso 1 1 calc R . .
C12 C 0.03597(9) 1.18347(10) -0.19071(19) 0.0357(3) Uani 1 1 d . . .
H12 H -0.0155 1.2162 -0.2415 0.043 Uiso 1 1 calc R . .
C11 C 0.03399(9) 1.08880(10) -0.1762(2) 0.0362(3) Uani 1 1 d . . .
H11 H -0.0191 1.0563 -0.2178 0.043 Uiso 1 1 calc R . .
C10 C 0.10906(9) 1.03832(9) -0.10070(18) 0.0308(3) Uani 1 1 d . . .
H10 H 0.1062 0.9725 -0.0910 0.037 Uiso 1 1 calc R . .
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'
O O 0.0492 0.0322 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 O1 C3 115.44(9) . .
C1 N1 N2 119.06(10) . .
N1 N2 C9 119.35(10) . .
N1 N2 H2 120.3 . .
C9 N2 H2 120.3 . .
C5 N5 C7 105.42(11) . .
C5 N4 C6 106.56(10) . .
C5 N4 C8 129.35(11) . .
C6 N4 C8 123.99(11) . .
C17 N3 C14 117.12(12) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
O1 C3 C4 106.90(10) . .
O1 C3 H3A 110.3 . .
C4 C3 H3A 110.3 . .
O1 C3 H3B 110.3 . .
C4 C3 H3B 110.3 . .
H3A C3 H3B 108.6 . .
O2 C2 O1 123.96(11) . .
O2 C2 C1 122.81(11) . .
O1 C2 C1 113.21(10) . .
N1 C1 C5 124.53(11) . .
N1 C1 C2 115.41(11) . .
C5 C1 C2 119.89(10) . .
C10 C9 N2 123.88(12) . .
C10 C9 C14 120.05(11) . .
N2 C9 C14 116.05(11) . .
N3 C14 C13 123.47(12) . .
N3 C14 C9 117.47(11) . .
C13 C14 C9 119.06(12) . .
C12 C13 C15 124.01(12) . .
C12 C13 C14 119.39(12) . .
C15 C13 C14 116.60(13) . .
C16 C15 C13 119.76(13) . .
C16 C15 H15 120.1 . .
C13 C15 H15 120.1 . .
C15 C16 C17 119.16(12) . .
C15 C16 H16 120.4 . .
C17 C16 H16 120.4 . .
N5 C5 N4 111.10(11) . .
N5 C5 C1 122.14(11) . .
N4 C5 C1 126.63(11) . .
C6 C7 N5 110.13(12) . .
C6 C7 H7 124.9 . .
N5 C7 H7 124.9 . .
C7 C6 N4 106.77(12) . .
C7 C6 H6 126.6 . .
N4 C6 H6 126.6 . .
N4 C8 H8A 109.5 . .
N4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
N4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
N3 C17 C16 123.86(13) . .
N3 C17 H17 118.1 . .
C16 C17 H17 118.1 . .
C11 C12 C13 120.19(12) . .
C11 C12 H12 119.9 . .
C13 C12 H12 119.9 . .
C12 C11 C10 121.29(13) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C9 C10 C11 120.00(12) . .
C9 C10 H10 120.0 . .
C11 C10 H10 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.3342(15) .
O1 C3 1.4568(15) .
O2 C2 1.2101(15) .
N1 C1 1.3029(16) .
N1 N2 1.3362(14) .
N2 C9 1.3903(16) .
N2 H2 0.8800 .
N5 C5 1.3326(16) .
N5 C7 1.3660(18) .
N4 C5 1.3620(16) .
N4 C6 1.3672(17) .
N4 C8 1.4641(16) .
N3 C17 1.3171(17) .
N3 C14 1.3630(17) .
C4 C3 1.4991(19) .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C2 C1 1.4900(17) .
C1 C5 1.4708(17) .
C9 C10 1.3734(18) .
C9 C14 1.4302(17) .
C14 C13 1.4153(18) .
C13 C12 1.412(2) .
C13 C15 1.4146(19) .
C15 C16 1.356(2) .
C15 H15 0.9500 .
C16 C17 1.407(2) .
C16 H16 0.9500 .
C7 C6 1.357(2) .
C7 H7 0.9500 .
C6 H6 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C17 H17 0.9500 .
C12 C11 1.365(2) .
C12 H12 0.9500 .
C11 C10 1.4077(19) .
C11 H11 0.9500 .
C10 H10 0.9500 .
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
N2 H2 N5 0.88 2.08 2.7313(15) 129.7 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C1 N1 N2 C9 -178.11(10) . . . .
C2 O1 C3 C4 -175.39(10) . . . .
C3 O1 C2 O2 -3.42(17) . . . .
C3 O1 C2 C1 177.94(10) . . . .
N2 N1 C1 C5 0.06(17) . . . .
N2 N1 C1 C2 175.31(10) . . . .
O2 C2 C1 N1 -161.28(12) . . . .
O1 C2 C1 N1 17.37(15) . . . .
O2 C2 C1 C5 14.21(18) . . . .
O1 C2 C1 C5 -167.13(10) . . . .
N1 N2 C9 C10 -6.12(18) . . . .
N1 N2 C9 C14 172.67(10) . . . .
C17 N3 C14 C13 0.18(17) . . . .
C17 N3 C14 C9 -179.21(11) . . . .
C10 C9 C14 N3 -178.99(11) . . . .
N2 C9 C14 N3 2.18(16) . . . .
C10 C9 C14 C13 1.60(17) . . . .
N2 C9 C14 C13 -177.24(10) . . . .
N3 C14 C13 C12 178.88(12) . . . .
C9 C14 C13 C12 -1.74(17) . . . .
N3 C14 C13 C15 -1.40(18) . . . .
C9 C14 C13 C15 177.98(11) . . . .
C12 C13 C15 C16 -179.18(13) . . . .
C14 C13 C15 C16 1.12(18) . . . .
C13 C15 C16 C17 0.3(2) . . . .
C7 N5 C5 N4 -1.24(14) . . . .
C7 N5 C5 C1 -177.32(11) . . . .
C6 N4 C5 N5 0.83(14) . . . .
C8 N4 C5 N5 -175.59(12) . . . .
C6 N4 C5 C1 176.69(12) . . . .
C8 N4 C5 C1 0.3(2) . . . .
N1 C1 C5 N5 31.47(18) . . . .
C2 C1 C5 N5 -143.59(12) . . . .
N1 C1 C5 N4 -143.97(13) . . . .
C2 C1 C5 N4 40.97(17) . . . .
C5 N5 C7 C6 1.20(15) . . . .
N5 C7 C6 N4 -0.72(15) . . . .
C5 N4 C6 C7 -0.05(14) . . . .
C8 N4 C6 C7 176.61(11) . . . .
C14 N3 C17 C16 1.38(19) . . . .
C15 C16 C17 N3 -1.6(2) . . . .
C15 C13 C12 C11 -178.88(13) . . . .
C14 C13 C12 C11 0.82(19) . . . .
C13 C12 C11 C10 0.3(2) . . . .
N2 C9 C10 C11 178.23(12) . . . .
C14 C9 C10 C11 -0.50(19) . . . .
C12 C11 C10 C9 -0.5(2) . . . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 57371156
