Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl} ethanone O-ethyl-oxime, C17H17ClN2O2
Zhao, Ji-Xing; Zhao, Li; Liu, Guo-Hua; Li, Peng-Peng; Zhu, Zhao-Bin; Zeitschrift für Kristallographie - New Crystal Structures 232 (2017) 999–1001; doi:10.1515/ncrs-2017-0129

data_8106747
_publ_section_title
;
 Crystal structure of 1-{4-[(5-Chloro-2-hydroxy-benzylidene)amino]phenyl}
 ethanone O-ethyl-oxime, C17H17ClN2O2
;
_journal_issue                   6
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              999
_journal_page_last               1001
_journal_paper_doi               10.1515/ncrs-2017-0129
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C17 H17 Cl N2 O2'
_chemical_formula_sum            'C17 H17 Cl N2 O2'
_chemical_formula_weight         316.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_cell_angle_alpha                90
_cell_angle_beta                 97.513(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   17.789(2)
_cell_length_b                   7.1127(7)
_cell_length_c                   6.2885(6)
_cell_measurement_reflns_used    768
_cell_measurement_temperature    290.83(10)
_cell_measurement_theta_max      24.2080
_cell_measurement_theta_min      4.3380
_cell_volume                     788.84(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.83(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -14.00   25.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000 -180.0000 26

  2 omega  -43.00   65.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000   90.0000 72

  3 omega  -39.00   48.00   1.5000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -77.0000   60.0000 58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0367190000
_diffrn_orient_matrix_UB_12      -0.0398239000
_diffrn_orient_matrix_UB_13      0.0045801000
_diffrn_orient_matrix_UB_21      0.0165634000
_diffrn_orient_matrix_UB_22      0.0888175000
_diffrn_orient_matrix_UB_23      0.0280653000
_diffrn_orient_matrix_UB_31      -0.0002713000
_diffrn_orient_matrix_UB_32      -0.0210902000
_diffrn_orient_matrix_UB_33      0.1101372000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0215
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            2947
_diffrn_reflns_point_group_measured_fraction_full 0.741
_diffrn_reflns_point_group_measured_fraction_max 0.741
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_min         3.466
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Flack x determined using 424 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.28(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2300
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0600
_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^)+(0.0623P)^2^+0.2976P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1399
_refine_ls_wR_factor_ref         0.1651
_reflns_Friedel_coverage         0.483
_reflns_Friedel_fraction_full    0.484
_reflns_Friedel_fraction_max     0.484
_reflns_number_gt                1661
_reflns_number_total             2300
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2017-0129_suppl.cif
_cod_data_source_block           d910
_cod_original_cell_volume        788.83(15)
_cod_database_code               8106747
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H15A,H15B,H15C} of C15, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, {H17A,H17B,H17C} of C17
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C3(H3), C4(H4), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'