#------------------------------------------------------------------------------
#$Date: 2019-09-18 16:35:48 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/03/7200346.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_7200346
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            'C16 H14 F2 N2 O2'
_chemical_formula_weight         304.29
_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                90.00
_cell_angle_beta                 94.019(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7199(4)
_cell_length_b                   5.7814(3)
_cell_length_c                   32.4814(17)
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      1.26
_cell_volume                     1446.14(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            18570
_diffrn_reflns_theta_full        27.99
_diffrn_reflns_theta_max         27.99
_diffrn_reflns_theta_min         1.26
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    .
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.042
_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     199
_refine_ls_number_reflns         3446
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0548
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0980P)²+0.2928P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1670
_refine_ls_wR_factor_ref         0.1817
_reflns_number_gt                2440
_reflns_number_total             3446
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B813263A.txt
_cod_data_source_block           2F
_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      P2(1)/c
_cod_database_code               7200346
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F14 F 0.05746(18) 0.3264(3) 0.23652(3) 0.0826(4) Uani 1 1 d . . .
F24 F 0.46221(19) 1.1458(3) -0.23624(4) 0.0862(4) Uani 1 1 d . . .
N11 N 0.23257(17) 0.4758(2) 0.07720(4) 0.0497(4) Uani 1 1 d . . .
H11 H 0.3174 0.3912 0.0703 0.060 Uiso 1 1 calc R . .
C11 C 0.17799(19) 0.4398(3) 0.11748(4) 0.0427(4) Uani 1 1 d . . .
C12 C 0.2293(2) 0.2366(3) 0.13749(5) 0.0529(4) Uani 1 1 d . . .
H12 H 0.2907 0.1256 0.1238 0.063 Uiso 1 1 calc R . .
C13 C 0.1897(2) 0.1986(3) 0.17755(6) 0.0584(5) Uani 1 1 d . . .
H13 H 0.2240 0.0628 0.1911 0.070 Uiso 1 1 calc R . .
C14 C 0.0984(2) 0.3647(3) 0.19718(5) 0.0549(4) Uani 1 1 d . . .
C15 C 0.0459(2) 0.5664(3) 0.17834(5) 0.0536(4) Uani 1 1 d . . .
H15 H -0.0162 0.6757 0.1923 0.064 Uiso 1 1 calc R . .
C16 C 0.0866(2) 0.6049(3) 0.13811(5) 0.0480(4) Uani 1 1 d . . .
H16 H 0.0527 0.7419 0.1249 0.058 Uiso 1 1 calc R . .
N21 N 0.25962(18) 1.0228(3) -0.07838(4) 0.0548(4) Uani 1 1 d . . .
H21 H 0.1772 1.1096 -0.0708 0.066 Uiso 1 1 calc R . .
C21 C 0.31582(19) 1.0538(3) -0.11914(5) 0.0456(4) Uani 1 1 d . . .
C22 C 0.3993(2) 1.2551(3) -0.12938(6) 0.0573(4) Uani 1 1 d . . .
H22 H 0.4220 1.3695 -0.1096 0.069 Uiso 1 1 calc R . .
C23 C 0.4490(2) 1.2857(3) -0.16905(6) 0.0621(5) Uani 1 1 d . . .
H23 H 0.5064 1.4197 -0.1762 0.074 Uiso 1 1 calc R . .
C24 C 0.4123(2) 1.1160(3) -0.19748(5) 0.0562(4) Uani 1 1 d . . .
C25 C 0.3294(3) 0.9165(3) -0.18827(5) 0.0591(5) Uani 1 1 d . . .
H25 H 0.3063 0.8035 -0.2083 0.071 Uiso 1 1 calc R . .
C26 C 0.2804(2) 0.8859(3) -0.14854(5) 0.0537(4) Uani 1 1 d . . .
H26 H 0.2233 0.7512 -0.1416 0.064 Uiso 1 1 calc R . .
O31 O 0.0397(3) 0.7408(4) 0.05313(5) 0.1287(9) Uani 1 1 d . . .
O34 O 0.4503(2) 0.7470(3) -0.05911(4) 0.0910(6) Uani 1 1 d . . .
C31 C 0.1688(3) 0.6242(4) 0.04894(6) 0.0697(6) Uani 1 1 d . . .
C32 C 0.2649(3) 0.6360(4) 0.01002(6) 0.0824(8) Uani 1 1 d . . .
H32A H 0.3877 0.6118 0.0171 0.099 Uiso 1 1 calc . . .
H32B H 0.2245 0.5120 -0.0083 0.099 Uiso 1 1 calc . . .
C33 C 0.2416(3) 0.8561(4) -0.01163(6) 0.0784(7) Uani 1 1 d . . .
H33A H 0.2880 0.9786 0.0063 0.094 Uiso 1 1 calc . . .
H33B H 0.1182 0.8842 -0.0170 0.094 Uiso 1 1 calc . . .
C34 C 0.3269(2) 0.8687(3) -0.05180(5) 0.0581(5) Uani 1 1 d . . .
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
C31 N11 C11 127.88(13) . . ?
C16 C11 C12 119.65(14) . . ?
C16 C11 N11 122.61(14) . . ?
C12 C11 N11 117.60(13) . . ?
C13 C12 C11 120.24(15) . . ?
C12 C13 C14 118.87(16) . . ?
F14 C14 C15 118.71(16) . . ?
F14 C14 C13 118.96(16) . . ?
C15 C14 C13 122.33(15) . . ?
C14 C15 C16 118.74(15) . . ?
C15 C16 C11 120.17(15) . . ?
C34 N21 C21 123.88(13) . . ?
C26 C21 C22 120.03(15) . . ?
C26 C21 N21 119.65(15) . . ?
C22 C21 N21 120.28(15) . . ?
C23 C22 C21 119.82(16) . . ?
C24 C23 C22 118.77(17) . . ?
F24 C24 C25 118.74(17) . . ?
F24 C24 C23 118.65(17) . . ?
C25 C24 C23 122.61(16) . . ?
C24 C25 C26 118.51(17) . . ?
C21 C26 C25 120.25(16) . . ?
O31 C31 N11 123.20(16) . . ?
O31 C31 C32 121.44(16) . . ?
N11 C31 C32 115.35(14) . . ?
C33 C32 C31 113.05(16) . . ?
C32 C33 C34 114.46(16) . . ?
O34 C34 N21 122.53(15) . . ?
O34 C34 C33 122.39(16) . . ?
N21 C34 C33 115.07(14) . . ?
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
F14 C14 1.3557(18) . ?
F24 C24 1.3532(18) . ?
N11 C31 1.326(2) . ?
N11 C11 1.4177(18) . ?
C11 C16 1.387(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.375(2) . ?
C13 C14 1.374(3) . ?
C14 C15 1.365(3) . ?
C15 C16 1.383(2) . ?
N21 C34 1.321(2) . ?
N21 C21 1.4331(19) . ?
C21 C26 1.376(2) . ?
C21 C22 1.382(2) . ?
C22 C23 1.381(2) . ?
C23 C24 1.364(3) . ?
C24 C25 1.362(3) . ?
C25 C26 1.381(2) . ?
O31 C31 1.218(2) . ?
O34 C34 1.2210(19) . ?
C31 C32 1.512(2) . ?
C32 C33 1.459(3) . ?
C33 C34 1.504(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 421164
