#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:35:16 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180188 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/84/7108487.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_7108487
loop_
_publ_author_name
'Xin Su'
'Mart Lokov'
'Agnes Kutt'
'Ivo Leito'
'Ivan Aprahamian'
_publ_section_title
;
 Unusual para-substituent effects on the intramolecular hydrogen-bond in
 hydrazone-based switches
;
_journal_name_full               Chem.Commun.
_journal_page_first              10490
_journal_paper_doi               10.1039/c2cc35860c
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C17 H20 N4 O2'
_chemical_formula_sum            'C17 H20 N4 O2'
_chemical_formula_weight         312.37
_space_group_IT_number           14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 93.5940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.9390(13)
_cell_length_b                   7.5769(5)
_cell_length_c                   11.1814(8)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      2.15
_cell_volume                     1601.36(19)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25125
_diffrn_reflns_theta_full        25.32
_diffrn_reflns_theta_max         25.32
_diffrn_reflns_theta_min         2.15
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0324
_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)+(0.0458P)²+0.4362P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                2613
_reflns_number_total             2925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc35860c.txt
_cod_data_source_block           ia2211
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7108487
#BEGIN Tags that were not found in dictionaries:
_contact_crystallographer_name   'Richard Staples'
_contact_crystallographer_email  staples@chemistry.msu.com
#END Tags that were not found in dictionaries
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
O1 O 0.72328(4) 0.55732(13) 0.45185(7) 0.0392(2) Uani 1 1 d .
O2 O 0.61142(4) 0.62110(13) 0.48867(8) 0.0407(2) Uani 1 1 d .
N1 N 0.77380(5) 0.39159(13) 0.77390(8) 0.0273(2) Uani 1 1 d .
H1 H 0.7433 0.3630 0.8268 0.033 Uiso 1 1 calc R
N2 N 0.75128(5) 0.45300(12) 0.66817(8) 0.0269(2) Uani 1 1 d .
N3 N 0.64171(5) 0.41177(14) 0.83392(9) 0.0313(2) Uani 1 1 d .
N5 N 1.06365(5) 0.32572(14) 0.89955(8) 0.0294(2) Uani 1 1 d .
C1 C 0.84674(6) 0.37183(14) 0.80211(9) 0.0239(2) Uani 1 1 d .
C2 C 0.89684(6) 0.43599(14) 0.72764(9) 0.0251(2) Uani 1 1 d .
H2 H 0.8818 0.4905 0.6539 0.030 Uiso 1 1 calc R
C3 C 0.96812(6) 0.42139(15) 0.75966(9) 0.0253(2) Uani 1 1 d .
H3 H 1.0014 0.4667 0.7075 0.030 Uiso 1 1 calc R
C4 C 0.99257(6) 0.34098(14) 0.86782(9) 0.0236(2) Uani 1 1 d .
C5 C 0.94094(6) 0.27554(15) 0.94143(9) 0.0262(2) Uani 1 1 d .
H5 H 0.9555 0.2202 1.0151 0.031 Uiso 1 1 calc R
C6 C 0.86948(6) 0.29000(15) 0.90887(10) 0.0269(2) Uani 1 1 d .
H6 H 0.8357 0.2437 0.9599 0.032 Uiso 1 1 calc R
C7 C 1.11533(6) 0.41534(18) 0.83173(11) 0.0356(3) Uani 1 1 d .
H7A H 1.1148 0.3650 0.7510 0.053 Uiso 1 1 calc R
H7B H 1.1625 0.4006 0.8719 0.053 Uiso 1 1 calc R
H7C H 1.1037 0.5413 0.8264 0.053 Uiso 1 1 calc R
C8 C 1.08694(6) 0.24822(17) 1.01339(10) 0.0319(3) Uani 1 1 d .
H8A H 1.0714 0.3223 1.0786 0.048 Uiso 1 1 calc R
H8B H 1.1387 0.2399 1.0192 0.048 Uiso 1 1 calc R
H8C H 1.0665 0.1300 1.0195 0.048 Uiso 1 1 calc R
C9 C 0.68349(6) 0.47371(15) 0.63970(10) 0.0264(2) Uani 1 1 d .
C10 C 0.66781(6) 0.55649(16) 0.52075(10) 0.0284(3) Uani 1 1 d .
C11 C 0.71381(7) 0.65174(18) 0.33882(11) 0.0360(3) Uani 1 1 d .
H11A H 0.7593 0.7059 0.3196 0.043 Uiso 1 1 calc R
H11B H 0.6790 0.7478 0.3467 0.043 Uiso 1 1 calc R
C12 C 0.68866(8) 0.53161(18) 0.23880(12) 0.0428(3) Uani 1 1 d .
H12A H 0.7235 0.4377 0.2298 0.064 Uiso 1 1 calc R
H12B H 0.6828 0.5991 0.1641 0.064 Uiso 1 1 calc R
H12C H 0.6432 0.4793 0.2570 0.064 Uiso 1 1 calc R
C13 C 0.62451(6) 0.42875(14) 0.71525(10) 0.0264(2) Uani 1 1 d .
C14 C 0.55553(6) 0.39698(16) 0.66856(11) 0.0314(3) Uani 1 1 d .
H14 H 0.5438 0.4098 0.5852 0.038 Uiso 1 1 calc R
C15 C 0.50468(7) 0.34688(18) 0.74458(12) 0.0379(3) Uani 1 1 d .
H15 H 0.4580 0.3211 0.7136 0.046 Uiso 1 1 calc R
C16 C 0.52197(7) 0.33432(18) 0.86623(12) 0.0389(3) Uani 1 1 d .
H16 H 0.4874 0.3033 0.9205 0.047 Uiso 1 1 calc R
C17 C 0.59079(7) 0.36821(18) 0.90610(11) 0.0369(3) Uani 1 1 d .
H17 H 0.6028 0.3602 0.9897 0.044 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 0.0033 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 O1 C11 116.32(9)
N2 N1 C1 119.85(9)
N2 N1 H1 120.1
C1 N1 H1 120.1
C9 N2 N1 121.13(9)
C17 N3 C13 118.50(10)
C4 N5 C7 120.62(10)
C4 N5 C8 120.07(9)
C7 N5 C8 118.29(9)
C2 C1 C6 118.99(10)
C2 C1 N1 121.79(10)
C6 C1 N1 119.19(10)
C3 C2 C1 120.70(10)
C3 C2 H2 119.6
C1 C2 H2 119.6
C2 C3 C4 121.47(10)
C2 C3 H3 119.3
C4 C3 H3 119.3
N5 C4 C3 121.50(10)
N5 C4 C5 121.62(10)
C3 C4 C5 116.88(10)
C6 C5 C4 121.49(10)
C6 C5 H5 119.3
C4 C5 H5 119.3
C5 C6 C1 120.46(10)
C5 C6 H6 119.8
C1 C6 H6 119.8
N5 C7 H7A 109.5
N5 C7 H7B 109.5
H7A C7 H7B 109.5
N5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
N5 C8 H8A 109.5
N5 C8 H8B 109.5
H8A C8 H8B 109.5
N5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
N2 C9 C13 126.51(10)
N2 C9 C10 113.93(10)
C13 C9 C10 119.52(10)
O2 C10 O1 122.48(10)
O2 C10 C9 124.11(10)
O1 C10 C9 113.39(9)
O1 C11 C12 111.51(11)
O1 C11 H11A 109.3
C12 C11 H11A 109.3
O1 C11 H11B 109.3
C12 C11 H11B 109.3
H11A C11 H11B 108.0
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N3 C13 C14 120.82(10)
N3 C13 C9 115.94(10)
C14 C13 C9 123.17(10)
C15 C14 C13 119.37(11)
C15 C14 H14 120.3
C13 C14 H14 120.3
C14 C15 C16 119.65(12)
C14 C15 H15 120.2
C16 C15 H15 120.2
C17 C16 C15 117.87(11)
C17 C16 H16 121.1
C15 C16 H16 121.1
N3 C17 C16 123.73(12)
N3 C17 H17 118.1
C16 C17 H17 118.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C10 1.3411(14)
O1 C11 1.4535(14)
O2 C10 1.2087(14)
N1 N2 1.3163(13)
N1 C1 1.4057(14)
N1 H1 0.8800
N2 C9 1.3127(14)
N3 C17 1.3371(15)
N3 C13 1.3525(15)
N5 C4 1.3753(14)
N5 C7 1.4446(15)
N5 C8 1.4454(14)
C1 C2 1.3888(16)
C1 C6 1.3893(15)
C2 C3 1.3793(16)
C2 H2 0.9500
C3 C4 1.4065(15)
C3 H3 0.9500
C4 C5 1.4073(15)
C5 C6 1.3835(15)
C5 H5 0.9500
C6 H6 0.9500
C7 H7A 0.9800
C7 H7B 0.9800
C7 H7C 0.9800
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 C13 1.4817(15)
C9 C10 1.4836(16)
C11 C12 1.4965(19)
C11 H11A 0.9900
C11 H11B 0.9900
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 C14 1.3971(16)
C14 C15 1.3771(18)
C14 H14 0.9500
C15 C16 1.3823(19)
C15 H15 0.9500
C16 C17 1.3750(18)
C16 H16 0.9500
C17 H17 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
N1 H1 N3 0.88 1.96 2.6348(13) 131.9
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
C1 N1 N2 C9 -179.62(10)
N2 N1 C1 C2 8.33(16)
N2 N1 C1 C6 -173.37(10)
C6 C1 C2 C3 -0.98(16)
N1 C1 C2 C3 177.32(10)
C1 C2 C3 C4 0.26(16)
C7 N5 C4 C3 9.46(16)
C8 N5 C4 C3 177.71(10)
C7 N5 C4 C5 -171.12(11)
C8 N5 C4 C5 -2.87(16)
C2 C3 C4 N5 179.72(10)
C2 C3 C4 C5 0.28(16)
N5 C4 C5 C6 -179.55(10)
C3 C4 C5 C6 -0.10(16)
C4 C5 C6 C1 -0.61(17)
C2 C1 C6 C5 1.15(16)
N1 C1 C6 C5 -177.19(10)
N1 N2 C9 C13 -2.09(17)
N1 N2 C9 C10 175.71(10)
C11 O1 C10 O2 4.26(18)
C11 O1 C10 C9 -174.15(10)
N2 C9 C10 O2 -163.47(12)
C13 C9 C10 O2 14.50(18)
N2 C9 C10 O1 14.91(15)
C13 C9 C10 O1 -167.12(10)
C10 O1 C11 C12 -92.74(13)
C17 N3 C13 C14 -1.67(17)
C17 N3 C13 C9 -178.83(11)
N2 C9 C13 N3 19.48(17)
C10 C9 C13 N3 -158.21(10)
N2 C9 C13 C14 -157.60(11)
C10 C9 C13 C14 24.71(16)
N3 C13 C14 C15 -0.34(18)
C9 C13 C14 C15 176.60(11)
C13 C14 C15 C16 2.09(19)
C14 C15 C16 C17 -1.8(2)
C13 N3 C17 C16 2.01(19)
C15 C16 C17 N3 -0.3(2)
