Crystal structures of two dis-symmetric di-Schiff base compounds: 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol and 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol
Manawar, Rohit B.; Pashavan, Chandankumar T.; Shah, Manish K.; Jotani, Mukesh M.; Tiekink, Edward R. T.; Acta Crystallographica, Section E: Crystallographic Communications 76 (2020) 862–869; doi:10.1107/S2056989020006416

data_2022642
_publ_section_title
;
 Crystal structures of two dis-symmetric di-Schiff base compounds:
 2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol
 and
 4-bromo-2-({(E)-2-[(E)-2,6-dichlorobenzylidene]hydrazin-1-ylidene}methyl)phenol
;
_journal_coden_ASTM              ACSECI
_journal_coeditor_code           HB7915
_journal_issue                   6
_journal_name_full
;
 Acta Crystallographica, Section E: Crystallographic Communications
;
_journal_page_first              862
_journal_page_last               869
_journal_paper_doi               10.1107/S2056989020006416
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C15 H12 Cl2 N2 O2'
_chemical_formula_moiety         'C15 H12 Cl2 N2 O2'
_chemical_formula_sum            'C15 H12 Cl2 N2 O2'
_chemical_formula_weight         323.17
_chemical_name_systematic
2-({(<i>E</i>)-2-[(<i>E</i>)-2,6-Dichlorobenzylidene]hydrazin-1-ylidene}methyl)-6-methoxyphenol
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3556(2)
_cell_length_b                   12.8548(4)
_cell_length_c                   25.9904(9)
_cell_measurement_reflns_used    7669
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.9
_cell_measurement_theta_min      2.84
_cell_volume                     1455.21(10)
_computing_cell_refinement
;
APEX2/SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT (Bruker, 2004)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg,
2006)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
<i>SHELXL2014/7</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR92 (Altomare <i>et al.</i>,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            48935
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.807
_diffrn_reflns_theta_min         1.567
_diffrn_source                   'X-ray tube'
_exptl_absorpt_coefficient_mu    0.451
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1004 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013).
;
_refine_ls_abs_structure_Flack   0.12(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3751
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0465P)^2^+0.2295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2909
_reflns_number_total             3751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            hb7915sup1_I.cif
_cod_data_source_block           I
_cod_database_code               2022642
_publcif_datablock.id            {b9da7572-149f-4ef9-8e6e-1cb41469789c}
_shelx_shelxl_version_number     2018/3
_iucr_geom_hbonds_special_details
;
<i>Cg</i>1 is the  centroid of the (C9--14) ring.
;
_geom_extra_table_head_d
;
Summary of interaction energies (kJ mol^-1^) calculated for (I) and (II)
;
_geom_table_footnote_d
;
Notes: (<i>a</i>) Symmetry operations for (I): (i) -1 + <i>x</i>, <i>y</i>,
 <i>z</i>; 
(ii) -1/2 + <i>x</i>, 5/2 - <i>y</i>, - <i>z</i>; (iii) 1 + <i>x</i>,
 <i>y</i>, <i>z</i>.
(<i>b</i>) Symmetry operations for (II): (i) 1/2 + <i>x</i>, 3 - <i>y</i>,
 <i>z</i>;
(ii) -1/2 + <i>x</i>, 1 - <i>y</i>, <i>z</i>.
;
_shelx_estimated_absorpt_t_min   0.877
_shelx_estimated_absorpt_t_max   0.896
_shelx_res_checksum              63588
_shelx_hkl_checksum              37591
_cod_database_fobs_code 2022642