#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/32/63/4326355.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_4326355
loop_
_publ_author_name
'Hana Vaňkátová'
'Lies Broeckaert'
'Frank De Proft'
'Roman Olejník'
'Jan Turek'
'Zdeňka Padělková'
'Aleš R°užička'
_publ_section_title
;
 Tetrylenes Chelated by Hybrid Amido-Amino Ligand: Derivatives of
 2-[(N,N-Dimethylamino)methyl]aniline
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9454
_journal_page_last               9464
_journal_paper_doi               10.1021/ic2011056
_journal_volume                  50
_journal_year                    2011
_chemical_formula_moiety         'C7 H6 Cl N O2'
_chemical_formula_sum            'C7 H6 Cl N O2'
_chemical_formula_weight         171.58
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 118.809(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0329(6)
_cell_length_b                   8.3901(9)
_cell_length_c                   12.3520(7)
_cell_measurement_reflns_used    10274
_cell_measurement_temperature    150(1)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     729.45(11)
_computing_cell_refinement       'COLLECT and DENZO'
_computing_data_collection
'COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997)'
_computing_data_reduction        'COLLECT and DENZO'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150(1)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Nonius KappaCCD area detector'
_diffrn_measurement_method       'φ and ω scans to fill the Ewald sphere'
_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  0.0665
_diffrn_reflns_av_sigmaI/netI    0.0381
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10154
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.89
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
gaussian integration (Coppens, 1970)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0370
_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)+(0.0384P)²+0.3450P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0903
_reflns_number_gt                1377
_reflns_number_total             1647
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic2011056_si_001_12.cif
_cod_data_source_block           1-(chloromethyl)-2-nitrobenzene
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4326355
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 0.69639(7) 0.40939(5) 0.53246(4) 0.03482(15) Uani 1 1 d .
C2 C 0.7982(2) 0.1246(2) 0.47644(15) 0.0243(3) Uani 1 1 d .
N1 N 0.8343(2) 0.05016(19) 0.68320(13) 0.0297(3) Uani 1 1 d .
O2 O 0.7615(2) -0.0290(2) 0.73289(13) 0.0452(4) Uani 1 1 d .
O1 O 0.9488(2) 0.15647(18) 0.73514(12) 0.0417(4) Uani 1 1 d .
C1 C 0.7800(2) 0.0121(2) 0.55348(15) 0.0245(3) Uani 1 1 d .
C3 C 0.7437(2) 0.0740(2) 0.35619(16) 0.0283(4) Uani 1 1 d .
H3 H 0.7516 0.1452 0.3011 0.034 Uiso 1 1 d R
C5 C 0.6635(3) -0.1868(2) 0.39597(18) 0.0323(4) Uani 1 1 d .
H5 H 0.6201 -0.2897 0.3691 0.039 Uiso 1 1 d R
C7 C 0.8660(3) 0.2934(2) 0.50965(17) 0.0293(4) Uani 1 1 d .
H7A H 0.8829 0.3404 0.4439 0.035 Uiso 1 1 d R
H7B H 0.9877 0.2945 0.5846 0.035 Uiso 1 1 d R
C6 C 0.7138(2) -0.1411(2) 0.51506(17) 0.0297(4) Uani 1 1 d .
H6 H 0.7036 -0.2126 0.5691 0.036 Uiso 1 1 d R
C4 C 0.6783(3) -0.0787(2) 0.31648(17) 0.0318(4) Uani 1 1 d .
H4 H 0.6437 -0.1088 0.2359 0.038 Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0405(3) 0.0244(2) 0.0392(3) -0.00145(17) 0.0189(2) 0.00605(18)
C2 0.0244(8) 0.0240(8) 0.0255(8) 0.0020(6) 0.0129(7) 0.0038(6)
N1 0.0338(8) 0.0322(8) 0.0243(7) 0.0052(6) 0.0150(7) 0.0109(6)
O2 0.0600(10) 0.0517(9) 0.0362(8) 0.0088(7) 0.0330(7) 0.0042(7)
O1 0.0488(9) 0.0431(8) 0.0268(7) -0.0058(6) 0.0132(6) -0.0011(7)
C1 0.0250(8) 0.0263(8) 0.0225(8) 0.0023(6) 0.0118(6) 0.0055(7)
C3 0.0302(9) 0.0296(9) 0.0256(9) 0.0043(7) 0.0138(7) 0.0041(7)
C5 0.0317(9) 0.0242(8) 0.0381(10) -0.0049(7) 0.0145(8) 0.0001(7)
C7 0.0325(9) 0.0253(8) 0.0336(9) -0.0008(7) 0.0188(8) 0.0000(7)
C6 0.0313(9) 0.0253(9) 0.0341(9) 0.0058(7) 0.0171(8) 0.0042(7)
C4 0.0326(9) 0.0352(10) 0.0250(9) -0.0047(7) 0.0119(7) 0.0029(8)
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'
O O 0.0106 0.0060 '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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -1 0.051
1 0 1 0.044
-1 0 1 0.095
-1 0 -1 0.102
0 1 0 0.070
0 -1 0 0.073
0 0 1 0.067
0 0 -1 0.112
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 C2 C1 115.86(16)
C3 C2 C7 117.65(15)
C1 C2 C7 126.47(15)
O1 N1 O2 123.61(15)
O1 N1 C1 118.84(15)
O2 N1 C1 117.54(16)
C6 C1 C2 122.89(16)
C6 C1 N1 115.85(15)
C2 C1 N1 121.25(15)
C4 C3 C2 122.02(16)
C4 C3 H3 118.9
C2 C3 H3 119.0
C6 C5 C4 119.56(17)
C6 C5 H5 120.3
C4 C5 H5 120.1
C2 C7 Cl1 110.49(12)
C2 C7 H7A 109.5
Cl1 C7 H7A 109.4
C2 C7 H7B 109.6
Cl1 C7 H7B 109.6
H7A C7 H7B 108.1
C5 C6 C1 119.38(16)
C5 C6 H6 120.3
C1 C6 H6 120.4
C3 C4 C5 120.28(16)
C3 C4 H4 119.9
C5 C4 H4 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C7 1.8035(18)
C2 C3 1.397(2)
C2 C1 1.397(2)
C2 C7 1.501(2)
N1 O1 1.218(2)
N1 O2 1.227(2)
N1 C1 1.479(2)
C1 C6 1.384(3)
C3 C4 1.382(3)
C3 H3 0.9300
C5 C6 1.379(3)
C5 C4 1.383(3)
C5 H5 0.9300
C7 H7A 0.9701
C7 H7B 0.9700
C6 H6 0.9300
C4 H4 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 11427
