#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:20:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180501 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/70/7217037.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_7217037
loop_
_publ_author_name
'Ayhan, Mehmet Menaf'
'Zorlu, Yunus'
'Gökdemir, Özlem'
'Gürek, Ayşe Gül'
'Dumoulin, Fabienne'
'Ahsen, Vefa'
'Hirel, Catherine'
_publ_section_title
;
 Optimized synthesis and crystal growth by sublimation of
 1,3,3-trichloroisoindolenines, key building blocks for crosswise
 phthalocyanines
;
_journal_issue                   29
_journal_name_full               CrystEngComm
_journal_page_first              6556
_journal_paper_doi               10.1039/c4ce00189c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H4 Cl3 N '
_chemical_formula_sum            'C8 H4 Cl3 N'
_chemical_formula_weight         220.47
_chemical_name_common            1,1,3-trichloro-1H-isoindole
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.9288(3)
_cell_length_b                   6.9261(2)
_cell_length_c                   7.8324(2)
_cell_measurement_reflns_used    3568
_cell_measurement_temperature    170.(2)
_cell_measurement_theta_max      27.4827
_cell_measurement_theta_min      2.5573
_cell_volume                     864.11(4)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      170.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4573
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.56
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS
_exptl_absorpt_coefficient_mu    0.994
_exptl_absorpt_correction_T_max  0.85
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.695
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.353
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     70
_refine_ls_number_reflns         834
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.172
_refine_ls_R_factor_all          0.0230
_refine_ls_R_factor_gt           0.0220
_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)+(0.0346P)²+0.3110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                798
_reflns_number_total             834
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce00189c2.cif
_cod_data_source_block           I
_cod_database_code               7217037
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, 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
C C1 0.46107(12) 0.25 0.0210(3) 0.0198(4) Uani d S 1
C C2 0.54028(13) 0.25 -0.0524(3) 0.0239(5) Uani d S 1
H H2 0.5476 0.25 -0.1728 0.029 Uiso calc SR 1
C C3 0.60839(13) 0.25 0.0578(3) 0.0287(5) Uani d S 1
H H3 0.6636 0.25 0.0121 0.034 Uiso calc SR 1
C C4 0.59737(14) 0.25 0.2340(3) 0.0310(5) Uani d S 1
H H4 0.6453 0.25 0.3062 0.037 Uiso calc SR 1
C C5 0.51753(14) 0.25 0.3069(3) 0.0271(5) Uani d S 1
H H5 0.51 0.25 0.4272 0.033 Uiso calc SR 1
C C6 0.45003(12) 0.25 0.1967(3) 0.0202(4) Uani d S 1
C C7 0.35646(12) 0.25 0.2264(3) 0.0208(4) Uani d S 1
C C8 0.37599(13) 0.25 -0.0500(3) 0.0206(4) Uani d S 1
Cl Cl1 0.32265(2) 0.04078(6) 0.34040(5) 0.02707(16) Uani d . 1
Cl Cl2 0.35851(3) 0.25 -0.26481(6) 0.02851(18) Uani d S 1
N N1 0.31576(10) 0.25 0.0580(2) 0.0227(4) Uani d S 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C2 C1 C6 . . 121.76(19)
C2 C1 C8 . . 133.23(19)
C6 C1 C8 . . 105.00(17)
C3 C2 C1 . . 117.0(2)
C3 C2 H2 . . 121.5
C1 C2 H2 . . 121.5
C2 C3 C4 . . 121.24(19)
C2 C3 H3 . . 119.4
C4 C3 H3 . . 119.4
C3 C4 C5 . . 121.4(2)
C3 C4 H4 . . 119.3
C5 C4 H4 . . 119.3
C6 C5 C4 . . 117.1(2)
C6 C5 H5 . . 121.5
C4 C5 H5 . . 121.5
C5 C6 C1 . . 121.46(19)
C5 C6 C7 . . 132.38(19)
C1 C6 C7 . . 106.15(17)
N1 C7 C6 . . 107.32(16)
N1 C7 Cl1 . 7_565 108.40(8)
C6 C7 Cl1 . 7_565 112.04(9)
N1 C7 Cl1 . . 108.40(8)
C6 C7 Cl1 . . 112.04(9)
Cl1 C7 Cl1 7_565 . 108.52(11)
N1 C8 C1 . . 116.31(18)
N1 C8 Cl2 . . 122.01(16)
C1 C8 Cl2 . . 121.68(15)
C8 N1 C7 . . 105.22(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C2 . 1.386(3)
C1 C6 . 1.388(3)
C1 C8 . 1.465(3)
C2 C3 . 1.386(3)
C2 H2 . 0.95
C3 C4 . 1.391(4)
C3 H3 . 0.95
C4 C5 . 1.394(3)
C4 H4 . 0.95
C5 C6 . 1.379(3)
C5 H5 . 0.95
C6 C7 . 1.508(3)
C7 N1 . 1.469(3)
C7 Cl1 7_565 1.7853(12)
C7 Cl1 . 1.7853(12)
C8 N1 . 1.279(3)
C8 Cl2 . 1.706(2)
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
C6 C1 C2 C3 . . 0
C8 C1 C2 C3 . . 180.0
C1 C2 C3 C4 . . 0
C2 C3 C4 C5 . . 0
C3 C4 C5 C6 . . 0
C4 C5 C6 C1 . . 0
C4 C5 C6 C7 . . 180.0
C2 C1 C6 C5 . . 0
C8 C1 C6 C5 . . 180.0
C2 C1 C6 C7 . . 180.0
C8 C1 C6 C7 . . 0
C5 C6 C7 N1 . . 180.0
C1 C6 C7 N1 . . 0
C5 C6 C7 Cl1 . 7_565 61.12(10)
C1 C6 C7 Cl1 . 7_565 -118.88(10)
C5 C6 C7 Cl1 . . -61.12(10)
C1 C6 C7 Cl1 . . 118.88(10)
C2 C1 C8 N1 . . 180.0
C6 C1 C8 N1 . . 0
C2 C1 C8 Cl2 . . 0
C6 C1 C8 Cl2 . . 180.0
C1 C8 N1 C7 . . 0
Cl2 C8 N1 C7 . . 180.0
C6 C7 N1 C8 . . 0
Cl1 C7 N1 C8 7_565 . 121.19(8)
Cl1 C7 N1 C8 . . -121.19(8)
