#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/30/8103089.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_8103089
loop_
_publ_author_name
'Yu-Mei Hao'
_publ_section_title
;
 Crystal structure of 2-chloro-N'-(2-methoxy- benzylidene)benzohydrazide,
 C15H13ClN2O2
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              11
_journal_volume                  226
_journal_year                    2011
_chemical_formula_moiety         'C15 H13 Cl N2 O2'
_chemical_formula_sum            'C15 H13 Cl N2 O2'
_chemical_formula_weight         288.72
_chemical_name_systematic
; 
2-chloro-N'-(2-methoxybenzylidene)benzohydrazide, 
C₁₅H₁₃ClN₂O₂
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.587(2)
_cell_angle_beta                 95.724(2)
_cell_angle_gamma                93.646(2)
_cell_formula_units_Z            2
_cell_length_a                   4.9555(10)
_cell_length_b                   11.540(2)
_cell_length_c                   12.782(3)
_cell_measurement_reflns_used    1637
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.9
_cell_measurement_theta_min      2.8
_cell_volume                     689.9(2)
_computing_cell_refinement       SAINT
_computing_data_collection       SMART
_computing_data_reduction        SAINT
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 [12]'
_computing_structure_solution    'SHELXS-97 [11]'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω scans'
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5636
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.87
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.9411
_exptl_absorpt_correction_T_min  0.9285
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2938
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0446
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0514P)²+0.1470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2108
_reflns_number_total             2938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-3274.cff
_cod_data_source_block           3
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8103089
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.15282(12) 0.10504(5) 0.18460(5) 0.0683(2) Uani 1 1 d .
N1 N 0.7114(3) 0.23267(14) 0.54843(12) 0.0400(4) Uani 1 1 d .
N2 N 0.7138(3) 0.14238(14) 0.44823(12) 0.0377(4) Uani 1 1 d D
O1 O 1.2923(3) 0.50687(12) 0.62340(11) 0.0538(4) Uani 1 1 d .
O2 O 0.2582(3) 0.09558(15) 0.42657(13) 0.0648(5) Uani 1 1 d .
C1 C 0.9525(4) 0.40440(17) 0.68648(15) 0.0396(4) Uani 1 1 d .
C2 C 1.1427(4) 0.50600(17) 0.70730(16) 0.0422(5) Uani 1 1 d .
C3 C 1.1670(4) 0.59913(19) 0.80742(18) 0.0536(6) Uani 1 1 d .
H3 H 1.2938 0.6666 0.8212 0.064 Uiso 1 1 calc R
C4 C 1.0030(5) 0.5914(2) 0.88614(18) 0.0616(6) Uani 1 1 d .
H4 H 1.0220 0.6532 0.9536 0.074 Uiso 1 1 calc R
C5 C 0.8110(5) 0.4933(2) 0.86644(18) 0.0601(6) Uani 1 1 d .
H5 H 0.6984 0.4897 0.9196 0.072 Uiso 1 1 calc R
C6 C 0.7869(4) 0.4005(2) 0.76726(17) 0.0491(5) Uani 1 1 d .
H6 H 0.6575 0.3340 0.7542 0.059 Uiso 1 1 calc R
C7 C 0.9284(4) 0.30562(16) 0.58161(15) 0.0402(4) Uani 1 1 d .
H7 H 1.0718 0.2960 0.5390 0.048 Uiso 1 1 calc R
C8 C 0.4791(3) 0.07936(16) 0.39254(15) 0.0384(4) Uani 1 1 d .
C9 C 0.5115(3) -0.01092(16) 0.28395(15) 0.0364(4) Uani 1 1 d .
C10 C 0.3678(4) -0.00883(17) 0.18539(16) 0.0432(5) Uani 1 1 d .
C11 C 0.3972(4) -0.0929(2) 0.08549(17) 0.0539(6) Uani 1 1 d .
H11 H 0.2988 -0.0901 0.0206 0.065 Uiso 1 1 calc R
C12 C 0.5733(5) -0.1809(2) 0.08258(19) 0.0593(6) Uani 1 1 d .
H12 H 0.5940 -0.2380 0.0155 0.071 Uiso 1 1 calc R
C13 C 0.7184(4) -0.18469(19) 0.17851(19) 0.0549(6) Uani 1 1 d .
H13 H 0.8377 -0.2442 0.1761 0.066 Uiso 1 1 calc R
C14 C 0.6883(4) -0.10056(17) 0.27848(17) 0.0452(5) Uani 1 1 d .
H14 H 0.7877 -0.1040 0.3430 0.054 Uiso 1 1 calc R
C15 C 1.4823(5) 0.6103(2) 0.6398(2) 0.0628(6) Uani 1 1 d .
H15A H 1.3886 0.6827 0.6547 0.094 Uiso 1 1 calc R
H15B H 1.5696 0.6009 0.5743 0.094 Uiso 1 1 calc R
H15C H 1.6172 0.6170 0.7012 0.094 Uiso 1 1 calc R
H2 H 0.875(3) 0.130(2) 0.423(2) 0.080 Uiso 1 1 d 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'
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
C7 N1 N2 114.80(15)
C8 N2 N1 119.82(14)
C8 N2 H2 122.7(16)
N1 N2 H2 117.5(16)
C2 O1 C15 117.63(16)
C6 C1 C2 118.42(18)
C6 C1 C7 121.22(18)
C2 C1 C7 120.35(17)
O1 C2 C3 124.02(18)
O1 C2 C1 115.76(16)
C3 C2 C1 120.21(19)
C4 C3 C2 119.8(2)
C4 C3 H3 120.1
C2 C3 H3 120.1
C3 C4 C5 120.8(2)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C6 119.5(2)
C4 C5 H5 120.3
C6 C5 H5 120.3
C5 C6 C1 121.2(2)
C5 C6 H6 119.4
C1 C6 H6 119.4
N1 C7 C1 120.19(17)
N1 C7 H7 119.9
C1 C7 H7 119.9
O2 C8 N2 123.22(17)
O2 C8 C9 122.91(16)
N2 C8 C9 113.86(15)
C14 C9 C10 117.68(17)
C14 C9 C8 120.45(17)
C10 C9 C8 121.86(16)
C11 C10 C9 121.61(18)
C11 C10 Cl1 117.92(16)
C9 C10 Cl1 120.43(15)
C12 C11 C10 119.5(2)
C12 C11 H11 120.3
C10 C11 H11 120.3
C13 C12 C11 120.1(2)
C13 C12 H12 119.9
C11 C12 H12 119.9
C12 C13 C14 120.3(2)
C12 C13 H13 119.8
C14 C13 H13 119.8
C13 C14 C9 120.81(19)
C13 C14 H14 119.6
C9 C14 H14 119.6
O1 C15 H15A 109.5
O1 C15 H15B 109.5
H15A C15 H15B 109.5
O1 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C10 1.745(2)
N1 C7 1.274(2)
N1 N2 1.387(2)
N2 C8 1.342(2)
N2 H2 0.894(10)
O1 C2 1.365(2)
O1 C15 1.422(2)
O2 C8 1.222(2)
C1 C6 1.391(3)
C1 C2 1.398(3)
C1 C7 1.462(3)
C2 C3 1.389(3)
C3 C4 1.374(3)
C3 H3 0.9300
C4 C5 1.375(3)
C4 H4 0.9300
C5 C6 1.379(3)
C5 H5 0.9300
C6 H6 0.9300
C7 H7 0.9300
C8 C9 1.493(2)
C9 C14 1.388(3)
C9 C10 1.392(3)
C10 C11 1.378(3)
C11 C12 1.376(3)
C11 H11 0.9300
C12 C13 1.372(3)
C12 H12 0.9300
C13 C14 1.380(3)
C13 H13 0.9300
C14 H14 0.9300
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
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 O2 0.894(10) 1.965(14) 2.809(2) 157(2) 1_655
