#------------------------------------------------------------------------------
#$Date: 2019-09-18 16:35:48 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200349.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_7200349
loop_
_publ_author_name
'Samai, Suman'
'Biradha, Kumar'
_publ_section_title
;
 Halogen⋯halogen interactions in assembling β-sheets into 2D
 layers in the bis-(4-halo-phenylamido)alkanes and their co-crystals via
 inter-halogen interactions
;
_journal_coden_ASTM              CRECF4
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              482
_journal_page_last               492
_journal_paper_doi               10.1039/b813263a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C22 H26 F2 N2 O2'
_chemical_formula_weight         388.45
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                90.00
_cell_angle_beta                 99.817(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.1488(12)
_cell_length_b                   5.0327(3)
_cell_length_c                   43.840(3)
_cell_measurement_reflns_used    4263
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      0.94
_cell_volume                     3945.6(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD APEX 2 BRUKER'
_diffrn_measurement_method       hemisphere
_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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            25190
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         0.94
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       Needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0520
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0972P)²+1.8062P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1500
_refine_ls_wR_factor_ref         0.1700
_reflns_number_gt                2902
_reflns_number_total             4263
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B813263A.txt
_cod_data_source_block           5F
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7200349
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.50168(9) 0.3314(3) 0.09218(4) 0.0404(4) Uani 1 1 d . . .
H1 H 0.5079 0.4951 0.0876 0.048 Uiso 1 1 calc R . .
N2 N 0.82054(9) -0.2578(3) -0.15892(4) 0.0419(4) Uani 1 1 d . . .
H2 H 0.8165 -0.4186 -0.1528 0.050 Uiso 1 1 calc R . .
O1 O 0.52192(8) -0.0919(3) 0.07800(3) 0.0504(4) Uani 1 1 d . . .
O2 O 0.80903(11) 0.1724(3) -0.14573(4) 0.0664(5) Uani 1 1 d . . .
C1 C 0.52433(10) 0.1479(3) 0.07346(4) 0.0363(4) Uani 1 1 d . . .
C2 C 0.54963(11) 0.2623(4) 0.04500(5) 0.0425(5) Uani 1 1 d . . .
H2A H 0.5058 0.3092 0.0301 0.051 Uiso 1 1 calc . . .
H2B H 0.5773 0.4246 0.0508 0.051 Uiso 1 1 calc . . .
C3 C 0.59789(11) 0.0788(4) 0.02962(5) 0.0419(5) Uani 1 1 d . . .
H3A H 0.5725 -0.0904 0.0256 0.050 Uiso 1 1 calc . . .
H3B H 0.6443 0.0468 0.0437 0.050 Uiso 1 1 calc . . .
C4 C 0.61574(11) 0.1877(4) -0.00061(4) 0.0408(5) Uani 1 1 d . . .
H4A H 0.5692 0.2219 -0.0146 0.049 Uiso 1 1 calc . . .
H4B H 0.6416 0.3561 0.0035 0.049 Uiso 1 1 calc . . .
C5 C 0.66343(11) 0.0043(4) -0.01655(5) 0.0426(5) Uani 1 1 d . . .
H5A H 0.7106 -0.0254 -0.0028 0.051 Uiso 1 1 calc . . .
H5B H 0.6383 -0.1659 -0.0200 0.051 Uiso 1 1 calc . . .
C6 C 0.67946(11) 0.1077(4) -0.04717(4) 0.0418(5) Uani 1 1 d . . .
H6A H 0.7045 0.2781 -0.0437 0.050 Uiso 1 1 calc . . .
H6B H 0.6324 0.1365 -0.0610 0.050 Uiso 1 1 calc . . .
C7 C 0.72750(12) -0.0770(4) -0.06285(5) 0.0439(5) Uani 1 1 d . . .
H7A H 0.7030 -0.2486 -0.0659 0.053 Uiso 1 1 calc . . .
H7B H 0.7750 -0.1028 -0.0492 0.053 Uiso 1 1 calc . . .
C8 C 0.74232(12) 0.0238(4) -0.09393(4) 0.0425(5) Uani 1 1 d . . .
H8A H 0.6951 0.0437 -0.1079 0.051 Uiso 1 1 calc . . .
H8B H 0.7656 0.1976 -0.0911 0.051 Uiso 1 1 calc . . .
C9 C 0.79252(11) -0.1613(4) -0.10853(4) 0.0414(5) Uani 1 1 d . . .
H9A H 0.8398 -0.1809 -0.0946 0.050 Uiso 1 1 calc . . .
H9B H 0.7693 -0.3352 -0.1112 0.050 Uiso 1 1 calc . . .
C10 C 0.80747(11) -0.0639(4) -0.13940(4) 0.0402(5) Uani 1 1 d . . .
C11 C 0.46852(11) 0.2830(4) 0.11883(4) 0.0377(4) Uani 1 1 d . . .
F11 F 0.36690(11) 0.1839(3) 0.19438(4) 0.0919(6) Uani 1 1 d . . .
C12 C 0.41346(12) 0.4574(4) 0.12454(5) 0.0466(5) Uani 1 1 d . . .
H12 H 0.3992 0.5971 0.1109 0.056 Uiso 1 1 calc R . .
C13 C 0.37948(13) 0.4263(5) 0.15024(5) 0.0555(6) Uani 1 1 d . . .
H13 H 0.3426 0.5436 0.1541 0.067 Uiso 1 1 calc R . .
C14 C 0.40138(14) 0.2198(5) 0.16974(5) 0.0552(6) Uani 1 1 d . . .
C15 C 0.45654(14) 0.0458(5) 0.16511(5) 0.0565(6) Uani 1 1 d . . .
H15 H 0.4708 -0.0920 0.1790 0.068 Uiso 1 1 calc R . .
C16 C 0.49073(12) 0.0789(4) 0.13935(5) 0.0465(5) Uani 1 1 d . . .
H16 H 0.5285 -0.0364 0.1359 0.056 Uiso 1 1 calc R . .
F21 F 0.90466(13) -0.1728(4) -0.27342(4) 0.1101(7) Uani 1 1 d . . .
C21 C 0.84042(11) -0.2237(4) -0.18873(5) 0.0412(5) Uani 1 1 d . . .
C22 C 0.89079(14) -0.0335(5) -0.19419(6) 0.0594(6) Uani 1 1 d . . .
H22 H 0.9107 0.0835 -0.1785 0.071 Uiso 1 1 calc R . .
C23 C 0.91193(16) -0.0159(5) -0.22304(6) 0.0712(8) Uani 1 1 d . . .
H23 H 0.9457 0.1135 -0.2269 0.085 Uiso 1 1 calc R . .
C24 C 0.88274(17) -0.1893(5) -0.24544(6) 0.0673(7) Uani 1 1 d . . .
C25 C 0.83179(17) -0.3785(6) -0.24096(6) 0.0736(8) Uani 1 1 d . . .
H25 H 0.8118 -0.4931 -0.2569 0.088 Uiso 1 1 calc R . .
C26 C 0.81055(15) -0.3955(5) -0.21210(5) 0.0589(6) Uani 1 1 d . . .
H26 H 0.7760 -0.5233 -0.2085 0.071 Uiso 1 1 calc R . .
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C11 126.79(15) . . ?
C10 N2 C21 126.59(16) . . ?
O1 C1 N1 123.66(17) . . ?
O1 C1 C2 122.16(16) . . ?
N1 C1 C2 114.10(15) . . ?
C3 C2 C1 114.58(16) . . ?
C2 C3 C4 113.28(16) . . ?
C5 C4 C3 113.96(16) . . ?
C6 C5 C4 114.27(16) . . ?
C5 C6 C7 113.78(16) . . ?
C6 C7 C8 113.86(16) . . ?
C9 C8 C7 112.54(16) . . ?
C10 C9 C8 113.05(15) . . ?
O2 C10 N2 123.18(18) . . ?
O2 C10 C9 122.36(17) . . ?
N2 C10 C9 114.44(16) . . ?
C16 C11 C12 119.60(18) . . ?
C16 C11 N1 123.02(17) . . ?
C12 C11 N1 117.33(17) . . ?
C13 C12 C11 120.8(2) . . ?
C14 C13 C12 118.4(2) . . ?
F11 C14 C13 118.6(2) . . ?
F11 C14 C15 118.9(2) . . ?
C13 C14 C15 122.49(19) . . ?
C14 C15 C16 118.9(2) . . ?
C11 C16 C15 119.9(2) . . ?
C22 C21 C26 119.8(2) . . ?
C22 C21 N2 121.64(19) . . ?
C26 C21 N2 118.50(18) . . ?
C21 C22 C23 120.0(2) . . ?
C24 C23 C22 119.1(2) . . ?
C23 C24 F21 118.6(2) . . ?
C23 C24 C25 122.5(2) . . ?
F21 C24 C25 118.9(3) . . ?
C24 C25 C26 118.4(2) . . ?
C21 C26 C25 120.3(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.345(2) . ?
N1 C11 1.424(2) . ?
N2 C10 1.346(2) . ?
N2 C21 1.424(2) . ?
O1 C1 1.225(2) . ?
O2 C10 1.223(2) . ?
C1 C2 1.515(2) . ?
C2 C3 1.509(3) . ?
C3 C4 1.519(3) . ?
C4 C5 1.516(3) . ?
C5 C6 1.513(3) . ?
C6 C7 1.517(3) . ?
C7 C8 1.520(3) . ?
C8 C9 1.519(3) . ?
C9 C10 1.507(2) . ?
C11 C16 1.380(3) . ?
C11 C12 1.384(3) . ?
F11 C14 1.350(2) . ?
C12 C13 1.382(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.371(3) . ?
C15 C16 1.389(3) . ?
F21 C24 1.355(3) . ?
C21 C22 1.372(3) . ?
C21 C26 1.379(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.353(4) . ?
C24 C25 1.364(4) . ?
C25 C26 1.387(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12964413
