#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502289.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_1502289
loop_
_publ_author_name
'Ren, Changliang'
'Xu, Shengyu'
'Xu, Jun'
'Chen, Hongyu'
'Zeng, Huaqiang'
_publ_section_title
;
 Planar macrocyclic fluoropentamers as supramolecular organogelators.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3840
_journal_page_last               3843
_journal_paper_doi               10.1021/ol201361f
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C15 H10 F2 N2 O5'
_chemical_formula_weight         336.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 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                 93.890(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8822(5)
_cell_length_b                   14.1165(15)
_cell_length_c                   10.0699(11)
_cell_measurement_reflns_used    1620
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.54
_cell_measurement_theta_min      2.49
_cell_volume                     692.41(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4807
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.49
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.9917
_exptl_absorpt_correction_T_min  0.9013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs, (Sheldrick 2001)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.613
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ROD
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.76
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2423
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0552
_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)+(0.0875P)²+0.0489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1425
_refine_ls_wR_factor_ref         0.1498
_reflns_number_gt                2056
_reflns_number_total             2423
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201361f_si_002.cif
_cod_data_source_block           9061
_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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'Not Measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      Pc
_cod_database_code               1502289
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, 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
O1 O 0.5008(5) 0.19662(14) 0.5287(3) 0.0447(6) Uani 1 1 d .
O2 O -0.1999(8) -0.19404(16) 0.6791(3) 0.0687(9) Uani 1 1 d .
O3 O 0.0477(9) -0.29226(18) 0.5660(5) 0.0991(15) Uani 1 1 d .
O4 O -0.4459(7) 0.3590(2) 0.8560(4) 0.0766(10) Uani 1 1 d .
O5 O -0.3496(7) 0.50449(18) 0.8471(4) 0.0708(9) Uani 1 1 d .
F1 F -0.1324(4) 0.23847(11) 0.7458(2) 0.0414(5) Uani 1 1 d .
F2 F -0.1470(4) -0.01378(12) 0.6486(2) 0.0458(5) Uani 1 1 d .
N1 N -0.3139(6) 0.42316(18) 0.8156(3) 0.0435(7) Uani 1 1 d .
N2 N 0.0764(6) 0.13343(17) 0.5309(3) 0.0360(6) Uani 1 1 d .
H2N H -0.083(9) 0.142(3) 0.536(4) 0.041(10) Uiso 1 1 d .
C1 C -0.0394(6) 0.31297(19) 0.6833(3) 0.0302(6) Uani 1 1 d .
C2 C -0.1168(6) 0.4045(2) 0.7158(3) 0.0363(7) Uani 1 1 d .
C3 C -0.0088(7) 0.4821(2) 0.6537(4) 0.0443(8) Uani 1 1 d .
H3 H -0.0649 0.5435 0.6755 0.053 Uiso 1 1 calc R
C4 C 0.1807(7) 0.4695(2) 0.5601(4) 0.0463(8) Uani 1 1 d .
H4 H 0.2568 0.5222 0.5190 0.056 Uiso 1 1 calc R
C5 C 0.2585(7) 0.3788(2) 0.5269(4) 0.0418(7) Uani 1 1 d .
H5 H 0.3875 0.3703 0.4628 0.050 Uiso 1 1 calc R
C6 C 0.1483(6) 0.29944(19) 0.5873(3) 0.0345(7) Uani 1 1 d .
C7 C 0.2588(6) 0.2047(2) 0.5484(3) 0.0329(6) Uani 1 1 d .
C8 C 0.1537(6) 0.0399(2) 0.4955(3) 0.0354(7) Uani 1 1 d .
C9 C 0.3393(7) 0.0221(2) 0.4006(4) 0.0407(7) Uani 1 1 d .
H9 H 0.4153 0.0726 0.3546 0.049 Uiso 1 1 calc R
C10 C 0.4131(7) -0.0710(2) 0.3734(4) 0.0471(8) Uani 1 1 d .
H10 H 0.5418 -0.0834 0.3103 0.057 Uiso 1 1 calc R
C11 C 0.2976(7) -0.1442(2) 0.4389(4) 0.0473(9) Uani 1 1 d .
H11 H 0.3500 -0.2066 0.4205 0.057 Uiso 1 1 calc R
C12 C 0.1040(7) -0.1286(2) 0.5326(4) 0.0410(7) Uani 1 1 d .
C13 C 0.0342(6) -0.0349(2) 0.5596(3) 0.0376(7) Uani 1 1 d .
C14 C -0.0149(8) -0.2128(2) 0.5954(5) 0.0516(9) Uani 1 1 d .
C15 C -0.3201(15) -0.2755(3) 0.7394(6) 0.0858(17) Uani 1 1 d .
H15A H -0.3869 -0.3193 0.6705 0.129 Uiso 1 1 calc R
H15B H -0.4716 -0.2553 0.7902 0.129 Uiso 1 1 calc R
H15C H -0.1825 -0.3066 0.7982 0.129 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
C14 O2 C15 115.5(3)
O4 N1 O5 122.6(3)
O4 N1 C2 119.4(3)
O5 N1 C2 117.7(3)
C7 N2 C8 122.8(3)
F1 C1 C6 119.1(2)
F1 C1 C2 121.2(3)
C6 C1 C2 119.6(2)
C3 C2 C1 120.7(3)
C3 C2 N1 117.2(2)
C1 C2 N1 122.1(3)
C4 C3 C2 120.1(3)
C3 C4 C5 119.6(3)
C4 C5 C6 121.1(3)
C1 C6 C5 118.9(2)
C1 C6 C7 124.6(3)
C5 C6 C7 116.3(3)
O1 C7 N2 123.3(3)
O1 C7 C6 119.7(3)
N2 C7 C6 116.9(3)
C9 C8 C13 120.0(3)
C9 C8 N2 122.5(3)
C13 C8 N2 117.5(3)
C8 C9 C10 119.8(3)
C11 C10 C9 119.8(3)
C10 C11 C12 121.8(3)
C11 C12 C13 117.7(3)
C11 C12 C14 117.7(3)
C13 C12 C14 124.6(3)
F2 C13 C8 117.5(2)
F2 C13 C12 121.6(3)
C8 C13 C12 121.0(3)
O3 C14 O2 123.1(4)
O3 C14 C12 121.9(4)
O2 C14 C12 115.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.217(4)
O2 C14 1.303(5)
O2 C15 1.444(5)
O3 C14 1.205(5)
O4 N1 1.199(4)
O5 N1 1.207(3)
F1 C1 1.322(3)
F2 C13 1.335(4)
N1 C2 1.461(4)
N2 C7 1.347(4)
N2 C8 1.425(4)
C1 C6 1.389(4)
C1 C2 1.392(4)
C2 C3 1.383(4)
C3 C4 1.376(5)
C4 C5 1.383(4)
C5 C6 1.399(4)
C6 C7 1.504(4)
C8 C9 1.384(5)
C8 C13 1.386(4)
C9 C10 1.395(4)
C10 C11 1.368(5)
C11 C12 1.397(5)
C12 C13 1.398(4)
C12 C14 1.482(5)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2N O1 0.79(5) 2.17(4) 2.947(4) 167(4) 1_455
