#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/66/2236618.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_2236618
loop_
_publ_author_name
'Rivera, Augusto'
'Nerio, Luz Stella'
'Ríos-Motta, Jaime'
'Kučeráková, Monika'
'Dušek, Michal'
_publ_section_title
;
 4,4'-Difluoro-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol
;
_journal_coeditor_code           SJ5264
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3043
_journal_page_last               o3044
_journal_paper_doi               10.1107/S1600536812040329
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H18 F2 N2 O2'
_chemical_formula_moiety         'C17 H18 F2 N2 O2'
_chemical_formula_sum            'C17 H18 F2 N2 O2'
_chemical_formula_weight         320.3
_chemical_name_systematic
;
4,4'-Difluoro-2,2'-[imidazolidine-1,3-diylbis(methylene)]diphenol
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 99.4807(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5952(2)
_cell_length_b                   9.7018(2)
_cell_length_c                   16.2065(3)
_cell_measurement_reflns_used    21321
_cell_measurement_temperature    119.9(6)
_cell_measurement_theta_max      67.02
_cell_measurement_theta_min      4.55
_cell_volume                     1488.07(5)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2010)
;
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material
'JANA2006 (Petříček et al., 2006)'
_computing_structure_refinement
'JANA2006 (Petříček et al., 2006)'
_computing_structure_solution
'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      119.9
_diffrn_detector_area_resol_mean 10.3784
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'four-cycle diffractometer'
_diffrn_measurement_device_type  'Agilent Xcalibur (Atlas, Gemini ultra)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.007
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            35554
_diffrn_reflns_reduction_process
;
Integration of the CCD images was done by program CrysAlisPro
(Agilent Technologies, 2010). The same program was used for indexing of the
crystal shape and absorption correction.
;
_diffrn_reflns_theta_full        67.12
_diffrn_reflns_theta_max         67.12
_diffrn_reflns_theta_min         5.02
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.938
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2010)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.4294
_exptl_crystal_description       'polygon shape'
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.347
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.206
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_coef       9E2(4)
_refine_ls_extinction_method
'B-C type 1 Gaussian isotropic (Becker & Coppens, 1974)'
_refine_ls_goodness_of_fit_ref   2.21
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_constraints    66
_refine_ls_number_parameters     215
_refine_ls_number_reflns         2669
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.0092
_refine_ls_shift/su_mean         0.0011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                2452
_reflns_number_total             2669
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            sj5264.cif
_cod_data_source_block           I
_cod_original_sg_symbol_Hall     '-P 2yabc'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2236618
_cod_database_fobs_code          2236618
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 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_occupancy
_atom_site_symmetry_multiplicity
F F1 0.58488(7) 0.98624(8) 0.11639(4) 0.0290(2) Uani d 1 4
F F2 0.02275(8) 0.97367(8) 0.76918(5) 0.0339(3) Uani d 1 4
O O1 0.37960(8) 0.95183(9) 0.53830(5) 0.0225(3) Uani d 1 4
O O2 0.14871(8) 1.28848(8) 0.20259(5) 0.0238(3) Uani d 1 4
N N1 0.25088(9) 1.23815(10) 0.36231(6) 0.0205(3) Uani d 1 4
N N2 0.32537(9) 1.21463(10) 0.50457(5) 0.0193(3) Uani d 1 4
C C1 0.30030(12) 1.22156(12) 0.59151(7) 0.0211(3) Uani d 1 4
C C2 0.25940(11) 1.21368(11) 0.18359(7) 0.0203(3) Uani d 1 4
C C3 0.45165(11) 1.05403(12) 0.21953(7) 0.0210(3) Uani d 1 4
C C4 0.39919(12) 1.14642(12) 0.07918(7) 0.0245(3) Uani d 1 4
C C5 0.33984(11) 1.12752(12) 0.24310(6) 0.0195(3) Uani d 1 4
C C6 0.28663(11) 0.96039(12) 0.59366(7) 0.0196(3) Uani d 1 4
C C7 0.24230(11) 1.08848(12) 0.62013(6) 0.0189(3) Uani d 1 4
C C8 0.15072(11) 1.09088(12) 0.67872(7) 0.0217(3) Uani d 1 4
C C9 0.40565(12) 1.33344(13) 0.48144(7) 0.0248(3) Uani d 1 4
C C10 0.14906(12) 0.84193(13) 0.68378(7) 0.0239(3) Uani d 1 4
C C11 0.29049(12) 1.22389(12) 0.10290(7) 0.0236(3) Uani d 1 4
C C12 0.23894(11) 0.83887(12) 0.62461(7) 0.0222(3) Uani d 1 4
C C13 0.36823(12) 1.33886(12) 0.38570(7) 0.0240(4) Uani d 1 4
C C14 0.19724(11) 1.21598(12) 0.44037(6) 0.0206(3) Uani d 1 4
C C15 0.47692(11) 1.06297(12) 0.13855(7) 0.0223(3) Uani d 1 4
C C16 0.10847(12) 0.96840(13) 0.70989(7) 0.0241(4) Uani d 1 4
C C17 0.30169(11) 1.10785(12) 0.32918(7) 0.0211(3) Uani d 1 4
H H1c1 0.235801 1.295343 0.597024 0.0253 Uiso d 1 4
H H2c1 0.386945 1.24408 0.627648 0.0253 Uiso d 1 4
H H1c3 0.510721 0.997491 0.25954 0.0251 Uiso d 1 4
H H1c4 0.419502 1.150888 0.023184 0.0294 Uiso d 1 4
H H1c8 0.11748 1.177084 0.697131 0.026 Uiso d 1 4
H H1c9 0.504952 1.316125 0.497307 0.0297 Uiso d 1 4
H H2c9 0.372858 1.415883 0.504826 0.0297 Uiso d 1 4
H H1c10 0.116351 0.758191 0.705713 0.0286 Uiso d 1 4
H H1c11 0.236448 1.284933 0.063317 0.0283 Uiso d 1 4
H H1c12 0.26825 0.751886 0.605019 0.0266 Uiso d 1 4
H H1c13 0.335867 1.429715 0.368634 0.0288 Uiso d 1 4
H H2c13 0.448556 1.310747 0.361506 0.0288 Uiso d 1 4
H H1c14 0.151711 1.127692 0.438843 0.0247 Uiso d 1 4
H H2c14 0.138427 1.292231 0.450322 0.0247 Uiso d 1 4
H H1c17 0.229709 1.038565 0.326799 0.0253 Uiso d 1 4
H H2c17 0.382737 1.074935 0.36675 0.0253 Uiso d 1 4
H H2 0.1570(14) 1.2826(15) 0.2588(10) 0.0286 Uiso d 1 4
H H1 0.3808(15) 1.0424(16) 0.5183(9) 0.027 Uiso d 1 4
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
F 0.0727 0.0534 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 O1 H1 102.5(10)
C2 O2 H2 104.6(9)
C13 N1 C14 103.64(8)
C13 N1 C17 111.71(9)
C14 N1 C17 111.82(9)
C1 N2 C9 112.60(8)
C1 N2 C14 115.28(9)
C9 N2 C14 102.96(8)
N2 C1 C7 112.49(9)
N2 C1 H1c1 109.47
N2 C1 H2c1 109.47
C7 C1 H1c1 109.47
C7 C1 H2c1 109.47
H1c1 C1 H2c1 106.28
O2 C2 C5 121.43(10)
O2 C2 C11 118.03(9)
C5 C2 C11 120.53(10)
C5 C3 C15 119.60(10)
C5 C3 H1c3 120.2
C15 C3 H1c3 120.2
C11 C4 C15 117.95(11)
C11 C4 H1c4 121.03
C15 C4 H1c4 121.03
C2 C5 C3 118.46(10)
C2 C5 C17 121.24(10)
C3 C5 C17 120.20(9)
O1 C6 C7 121.16(10)
O1 C6 C12 118.35(10)
C7 C6 C12 120.48(10)
C1 C7 C6 121.21(10)
C1 C7 C8 120.01(10)
C6 C7 C8 118.62(10)
C7 C8 C16 119.41(11)
C7 C8 H1c8 120.29
C16 C8 H1c8 120.29
N2 C9 C13 103.87(9)
N2 C9 H1c9 109.47
N2 C9 H2c9 109.47
C13 C9 H1c9 109.47
C13 C9 H2c9 109.47
H1c9 C9 H2c9 114.55
C12 C10 C16 118.04(11)
C12 C10 H1c10 120.98
C16 C10 H1c10 120.98
C2 C11 C4 120.53(10)
C2 C11 H1c11 119.73
C4 C11 H1c11 119.73
C6 C12 C10 120.64(11)
C6 C12 H1c12 119.68
C10 C12 H1c12 119.68
N1 C13 C9 105.99(9)
N1 C13 H1c13 109.47
N1 C13 H2c13 109.47
C9 C13 H1c13 109.47
C9 C13 H2c13 109.47
H1c13 C13 H2c13 112.74
N1 C14 N2 103.95(8)
N1 C14 H1c14 109.47
N1 C14 H2c14 109.47
N2 C14 H1c14 109.47
N2 C14 H2c14 109.47
H1c14 C14 H2c14 114.48
F1 C15 C3 118.37(9)
F1 C15 C4 118.77(10)
C3 C15 C4 122.85(11)
F2 C16 C8 118.27(11)
F2 C16 C10 118.96(11)
C8 C16 C10 122.77(11)
N1 C17 C5 111.70(9)
N1 C17 H1c17 109.47
N1 C17 H2c17 109.47
C5 C17 H1c17 109.47
C5 C17 H2c17 109.47
H1c17 C17 H2c17 107.14
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 C15 1.3706(14)
F2 C16 1.3648(15)
O1 C6 1.3680(14)
O1 H1 0.937(16)
O2 C2 1.3628(14)
O2 H2 0.903(16)
N1 C13 1.4919(14)
N1 C14 1.4581(15)
N1 C17 1.4867(15)
N2 C1 1.4694(14)
N2 C9 1.4689(15)
N2 C14 1.4741(13)
C1 C7 1.5089(16)
C1 H1c1 0.96
C1 H2c1 0.96
C2 C5 1.4070(14)
C2 C11 1.3918(16)
C3 C5 1.3928(16)
C3 C15 1.3761(16)
C3 H1c3 0.96
C4 C11 1.3902(17)
C4 C15 1.3789(15)
C4 H1c4 0.96
C5 C17 1.5116(16)
C6 C7 1.4034(16)
C6 C12 1.3879(16)
C7 C8 1.3962(16)
C8 C16 1.3780(17)
C8 H1c8 0.96
C9 C13 1.5348(15)
C9 H1c9 0.96
C9 H2c9 0.96
C10 C12 1.3916(17)
C10 C16 1.3750(17)
C10 H1c10 0.96
C11 H1c11 0.96
C12 H1c12 0.96
C13 H1c13 0.96
C13 H2c13 0.96
C14 H1c14 0.96
C14 H2c14 0.96
C17 H1c17 0.96
C17 H2c17 0.96
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
_geom_hbond_publ_flag
O1 H1 N2 . 0.937(16) 1.756(16) 2.6413(12) 156.2(14) y
O2 H2 N1 . 0.903(16) 1.821(15) 2.6579(12) 153.2(13) y
C11 H1c11 O1 2_555 0.96 2.44 3.4001(13) 174.43 y
C17 H2c17 O1 3_676 0.96 2.55 3.4837(13) 166 y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658167
