#------------------------------------------------------------------------------
#$Date: 2017-07-26 08:39:43 +0300 (Wed, 26 Jul 2017) $
#$Revision: 199343 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/22/2242263.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_2242263
loop_
_publ_author_name
'Bao, Lipiao'
'Olmstead, Marilyn M.'
_publ_section_title
;
 A temperature-dependent phase transformation of
 (E)-2-[(4-chlorophenyl)imino]acenaphthylen-1-one
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1255
_journal_page_last               1258
_journal_paper_doi               10.1107/S2056989017010659
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C18 H10 Cl N O'
_chemical_formula_moiety         'C18 H10 Cl N O'
_chemical_formula_sum            'C18 H10 Cl N O'
_chemical_formula_weight         291.72
_chemical_name_common            MIAN
_chemical_name_systematic
(E)-2-[(4-Chlorophenyl)imino]acenaphthylen-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 92.959(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.0447(12)
_cell_length_b                   6.8764(9)
_cell_length_c                   10.9021(14)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      52.344
_cell_measurement_theta_min      5.710
_cell_volume                     677.15(15)
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_refinement
;
SHELXL2016/6 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      250(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5458
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.352
_diffrn_reflns_theta_min         2.255
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.684
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2014)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0390
_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/[σ²(Fo²)+(0.0370P)²+0.2756P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0914
_refine_ls_wR_factor_ref         0.0974
_reflns_number_gt                1227
_reflns_number_total             1496
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            su5384sup1.cif
_cod_data_source_block           alpha
_cod_database_code               2242263
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.946
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_occupancy
Cl Cl1 -0.05474(8) 0.250000 -0.19593(6) 0.0739(3) Uani d 1
O O1 0.75377(18) 0.250000 0.29014(16) 0.0547(5) Uani d 1
N N1 0.4932(2) 0.250000 0.12642(17) 0.0442(5) Uani d 1
C C1 0.4858(2) 0.250000 0.2426(2) 0.0366(5) Uani d 1
C C2 0.6292(2) 0.250000 0.3259(2) 0.0395(5) Uani d 1
C C3 0.5810(2) 0.250000 0.4537(2) 0.0366(5) Uani d 1
C C4 0.6571(3) 0.250000 0.5661(2) 0.0440(6) Uani d 1
H H4 0.761142 0.250000 0.571881 0.053 Uiso calc 1
C C5 0.5750(3) 0.250000 0.6722(2) 0.0475(6) Uani d 1
H H5 0.626114 0.250000 0.749460 0.057 Uiso calc 1
C C6 0.4230(3) 0.250000 0.6670(2) 0.0473(6) Uani d 1
H H6 0.372512 0.250000 0.740235 0.057 Uiso calc 1
C C7 0.1855(3) 0.250000 0.5310(2) 0.0564(7) Uani d 1
H H7 0.124153 0.250000 0.598029 0.068 Uiso calc 1
C C8 0.1232(3) 0.250000 0.4135(2) 0.0584(7) Uani d 1
H H8 0.019501 0.250000 0.402169 0.070 Uiso calc 1
C C9 0.2096(2) 0.250000 0.3087(2) 0.0455(6) Uani d 1
H H9 0.164153 0.250000 0.229206 0.055 Uiso calc 1
C C10 0.3610(2) 0.250000 0.32570(19) 0.0361(5) Uani d 1
C C11 0.4247(2) 0.250000 0.44731(19) 0.0347(5) Uani d 1
C C12 0.3414(3) 0.250000 0.5522(2) 0.0419(5) Uani d 1
C C13 0.3601(2) 0.250000 0.05083(19) 0.0398(5) Uani d 1
C C14 0.29812(19) 0.0762(3) 0.00977(15) 0.0479(4) Uani d 1
H H14 0.342774 -0.042208 0.033729 0.058 Uiso calc 1
C C15 0.17066(19) 0.0757(3) -0.06642(15) 0.0514(5) Uani d 1
H H15 0.127910 -0.042285 -0.093524 0.062 Uiso calc 1
C C16 0.1076(3) 0.250000 -0.1018(2) 0.0471(6) Uani d 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C1 N1 C13 . . 119.39(19)
N1 C1 C10 . . 133.5(2)
N1 C1 C2 . . 120.02(19)
C10 C1 C2 . . 106.45(17)
O1 C2 C3 . . 128.8(2)
O1 C2 C1 . . 125.3(2)
C3 C2 C1 . . 105.91(18)
C4 C3 C11 . . 119.9(2)
C4 C3 C2 . . 132.9(2)
C11 C3 C2 . . 107.22(19)
C3 C4 C5 . . 118.2(2)
C3 C4 H4 . . 120.9
C5 C4 H4 . . 120.9
C6 C5 C4 . . 122.4(2)
C6 C5 H5 . . 118.8
C4 C5 H5 . . 118.8
C5 C6 C12 . . 120.7(2)
C5 C6 H6 . . 119.7
C12 C6 H6 . . 119.7
C8 C7 C12 . . 120.6(2)
C8 C7 H7 . . 119.7
C12 C7 H7 . . 119.7
C7 C8 C9 . . 122.4(2)
C7 C8 H8 . . 118.8
C9 C8 H8 . . 118.8
C10 C9 C8 . . 118.6(2)
C10 C9 H9 . . 120.7
C8 C9 H9 . . 120.7
C9 C10 C11 . . 118.7(2)
C9 C10 C1 . . 134.7(2)
C11 C10 C1 . . 106.63(18)
C12 C11 C3 . . 122.6(2)
C12 C11 C10 . . 123.6(2)
C3 C11 C10 . . 113.79(19)
C11 C12 C7 . . 116.0(2)
C11 C12 C6 . . 116.3(2)
C7 C12 C6 . . 127.7(2)
C14 C13 C14 . 4_565 119.3(2)
C14 C13 N1 . . 120.24(11)
C14 C13 N1 4_565 . 120.24(11)
C13 C14 C15 . . 120.43(18)
C13 C14 H14 . . 119.8
C15 C14 H14 . . 119.8
C16 C15 C14 . . 119.13(18)
C16 C15 H15 . . 120.4
C14 C15 H15 . . 120.4
C15 C16 C15 4_565 . 121.4(2)
C15 C16 Cl1 4_565 . 119.28(11)
C15 C16 Cl1 . . 119.28(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cl1 C16 . 1.747(2)
O1 C2 . 1.211(3)
N1 C1 . 1.272(3)
N1 C13 . 1.423(3)
C1 C10 . 1.484(3)
C1 C2 . 1.545(3)
C2 C3 . 1.481(3)
C3 C4 . 1.373(3)
C3 C11 . 1.413(3)
C4 C5 . 1.406(3)
C4 H4 . 0.9400
C5 C6 . 1.373(4)
C5 H5 . 0.9400
C6 C12 . 1.420(3)
C6 H6 . 0.9400
C7 C8 . 1.372(4)
C7 C12 . 1.417(3)
C7 H7 . 0.9400
C8 C9 . 1.417(3)
C8 H8 . 0.9400
C9 C10 . 1.372(3)
C9 H9 . 0.9400
C10 C11 . 1.418(3)
C11 C12 . 1.402(3)
C13 C14 . 1.385(2)
C13 C14 4_565 1.385(2)
C14 C15 . 1.386(2)
C14 H14 . 0.9400
C15 C16 . 1.374(2)
C15 H15 . 0.9400
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
C6 H6 Cg 1_656 0.94 2.86 3.803(2) 177
C9 H9 Cg 1_555 0.94 2.88 3.668(11) 128
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C13 N1 C1 C10 . . 0.000000
C13 N1 C1 C2 . . 180.000000
N1 C1 C2 O1 . . 0.000000
C10 C1 C2 O1 . . 180.000000
N1 C1 C2 C3 . . 180.000000
C10 C1 C2 C3 . . 0.000000
O1 C2 C3 C4 . . 0.0000(10)
C1 C2 C3 C4 . . 180.000000
O1 C2 C3 C11 . . 180.000000
C1 C2 C3 C11 . . 0.000000
C11 C3 C4 C5 . . 0.0000(10)
C2 C3 C4 C5 . . 180.0000(10)
C3 C4 C5 C6 . . 0.0000(10)
C4 C5 C6 C12 . . 0.0000(10)
C12 C7 C8 C9 . . 0.0000(10)
C7 C8 C9 C10 . . 0.000000
C8 C9 C10 C11 . . 0.000000
C8 C9 C10 C1 . . 180.000000
N1 C1 C10 C9 . . 0.000000
C2 C1 C10 C9 . . 180.000000
N1 C1 C10 C11 . . 180.000000
C2 C1 C10 C11 . . 0.000000
C4 C3 C11 C12 . . 0.0000(10)
C2 C3 C11 C12 . . 180.000000
C4 C3 C11 C10 . . 180.000000
C2 C3 C11 C10 . . 0.000000
C9 C10 C11 C12 . . 0.000000
C1 C10 C11 C12 . . 180.000000
C9 C10 C11 C3 . . 180.000000
C1 C10 C11 C3 . . 0.000000
C3 C11 C12 C7 . . 180.000000
C10 C11 C12 C7 . . 0.0000(10)
C3 C11 C12 C6 . . 0.0000(10)
C10 C11 C12 C6 . . 180.000000
C8 C7 C12 C11 . . 0.0000(10)
C8 C7 C12 C6 . . 180.0000(10)
C5 C6 C12 C11 . . 0.0000(10)
C5 C6 C12 C7 . . 180.0000(10)
C1 N1 C13 C14 . . -92.57(18)
C1 N1 C13 C14 . 4_565 92.57(18)
C14 C13 C14 C15 4_565 . -3.4(3)
N1 C13 C14 C15 . . -178.35(17)
C13 C14 C15 C16 . . 0.7(3)
C14 C15 C16 C15 . 4_565 2.0(3)
C14 C15 C16 Cl1 . . -179.01(14)

_cod_database_fobs_code 2242263
