#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/85/2018532.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2018532
loop_
_publ_author_name
'Ojala, William H.'
'Arola, Trina M.'
'Brigino, Ann M.'
'Leavell, Jeremy D.'
'Ojala, Charles R.'
_publ_section_title
;
 Competing intermolecular interactions in some `bridge-flipped' isomeric
 phenylhydrazones
;
_journal_coeditor_code           FG3255
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o270
_journal_page_last               o278
_journal_paper_doi               10.1107/S0108270112026443
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C14 H10 Cl N3'
_chemical_formula_moiety         'C14 H10 Cl N3'
_chemical_formula_sum            'C14 H10 Cl N3'
_chemical_formula_weight         255.70
_chemical_melting_point_gt       451
_chemical_melting_point_lt       456
_chemical_name_systematic
;
(E)-4-cyanobenzaldehyde 4-chlorophenylhydrazone
;
_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           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.7790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7246(10)
_cell_length_b                   7.1767(6)
_cell_length_c                   16.3492(15)
_cell_measurement_reflns_used    3716
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.021
_cell_measurement_theta_min      2.838
_cell_volume                     1216.72(19)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω scans per φ'
_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  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0194
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11510
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         2.06
_exptl_absorpt_coefficient_mu    0.297
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0302
_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)+(0.0365P)²+0.2987P], P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                1952
_reflns_number_total             2154
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg3255.cif
_cod_data_source_block           Ia
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2018532
_cod_database_fobs_code          2018532
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.81863(4) 1.09092(5) -0.04948(2) 0.04344(15) Uani d P 0.9669(12) 1 . .
Cl Cl1A -0.020(2) 1.065(2) 0.3845(12) 0.032(4) Uiso d P 0.0331(12) 1 A 2
C C1 0.69784(12) 0.96031(18) 0.19029(8) 0.0302(3) Uani d . 1 1 A .
C C2 0.81968(13) 0.90738(18) 0.18230(9) 0.0325(3) Uani d . 1 1 . .
H H2 0.8772 0.8436 0.2274 0.039 Uiso calc R 1 1 . .
C C3 0.85700(13) 0.94691(19) 0.10946(9) 0.0346(3) Uani d . 1 1 . .
H H3 0.9400 0.9111 0.1044 0.042 Uiso calc R 1 1 . .
C C4 0.77251(13) 1.03919(19) 0.04366(9) 0.0331(3) Uani d . 1 1 . .
C C5 0.65171(13) 1.09237(19) 0.05032(9) 0.0343(3) Uani d . 1 1 . .
H H5 0.5946 1.1560 0.0049 0.041 Uiso calc R 1 1 . .
C C6 0.61411(13) 1.05271(19) 0.12323(9) 0.0334(3) Uani d . 1 1 . .
H H6 0.5308 1.0886 0.1277 0.040 Uiso calc R 1 1 . .
C C7 0.38895(13) 0.95124(18) 0.35319(8) 0.0301(3) Uani d . 1 1 A .
C C8 0.29058(13) 1.03183(19) 0.28922(9) 0.0330(3) Uani d . 1 1 . .
H H8 0.3086 1.0712 0.2380 0.040 Uiso calc R 1 1 . .
C C9 0.16883(13) 1.05405(19) 0.30017(9) 0.0342(3) Uani d . 1 1 A .
H H9 0.1030 1.1082 0.2565 0.041 Uiso calc R 1 1 . .
C C10 0.14167(13) 0.99703(18) 0.37549(8) 0.0305(3) Uani d . 1 1 . .
C C11 0.23750(13) 0.91580(19) 0.43940(9) 0.0342(3) Uani d . 1 1 A .
H H11 0.2190 0.8757 0.4904 0.041 Uiso calc R 1 1 . .
C C12 0.36004(14) 0.89413(19) 0.42772(9) 0.0339(3) Uani d . 1 1 . .
H H12 0.4257 0.8393 0.4713 0.041 Uiso calc R 1 1 A .
C C13 0.51839(13) 0.92277(18) 0.34294(8) 0.0322(3) Uani d . 1 1 . .
H H13 0.5848 0.8799 0.3894 0.039 Uiso calc R 1 1 A .
C C14 0.0146(2) 1.0235(3) 0.38803(12) 0.0356(5) Uani d . 1 1 A .
H H2N 0.7239(16) 0.885(2) 0.3088(11) 0.050(5) Uiso d . 1 1 . .
N N1 0.54374(10) 0.95508(16) 0.27155(7) 0.0316(3) Uani d . 1 1 A .
N N2 0.66378(11) 0.91805(17) 0.26445(8) 0.0349(3) Uani d . 1 1 . .
N N3 -0.08499(15) 1.0452(2) 0.39733(8) 0.0429(3) Uani d . 1 1 . .
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'
Cl Cl 0.1484 0.1585 '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
N2 C1 C6 122.08(12)
N2 C1 C2 118.90(12)
C6 C1 C2 119.02(13)
C3 C2 C1 120.58(13)
C3 C2 H2 120
C1 C2 H2 120
C2 C3 C4 119.49(13)
C2 C3 H3 120.
C4 C3 H3 120.
C5 C4 C3 120.78(13)
C5 C4 Cl1 119.15(11)
C3 C4 Cl1 120.07(11)
C4 C5 C6 119.80(13)
C4 C5 H5 120.
C6 C5 H5 120.
C5 C6 C1 120.32(13)
C5 C6 H6 120
C1 C6 H6 120
C12 C7 C8 118.64(12)
C12 C7 C13 119.42(12)
C8 C7 C13 121.93(12)
C9 C8 C7 120.60(13)
C9 C8 H8 120
C7 C8 H8 120
C8 C9 C10 120.03(12)
C8 C9 H9 120.
C10 C9 H9 120.
C11 C10 C9 120.27(12)
C11 C10 C14 119.46(13)
C9 C10 C14 120.27(14)
C12 C11 C10 119.23(13)
C12 C11 H11 120.
C10 C11 H11 120.
C11 C12 C7 121.23(13)
C11 C12 H12 119.
C7 C12 H12 119.
N1 C13 C7 120.56(12)
N1 C13 H13 120
C7 C13 H13 120
N3 C14 C10 179.5(2)
C13 N1 N2 118.06(11)
N1 N2 C1 120.18(11)
N1 N2 H2N 120.1(11)
C1 N2 H2N 118.9(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7567(14)
C1 N2 1.3861(18)
C1 C6 1.3949(19)
C1 C2 1.3986(19)
C2 C3 1.379(2)
C2 H2 0.95
C3 C4 1.385(2)
C3 H3 0.95
C4 C5 1.381(2)
C5 C6 1.382(2)
C5 H5 0.95
C6 H6 0.95
C7 C12 1.3935(19)
C7 C8 1.4065(19)
C7 C13 1.4546(19)
C8 C9 1.372(2)
C8 H8 0.95
C9 C10 1.3969(19)
C9 H9 0.95
C10 C11 1.3929(19)
C10 C14 1.442(3)
C11 C12 1.384(2)
C11 H11 0.95
C12 H12 0.95
C13 N1 1.2852(18)
C13 H13 0.95
C14 N3 1.127(3)
N1 N2 1.3482(16)
N2 H2N 0.871(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2N N3 1_655 0.871(17) 2.471(17) 3.1345(19) 133.5(14)
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
C12 C7 C13 N1 172.28(12)
C8 C7 C13 N1 -6.5(2)
C7 C13 N1 N2 -176.95(11)
C13 N1 N2 C1 -176.38(12)
C6 C1 N2 N1 4.40(19)
C2 C1 N2 N1 -175.13(12)
