#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/17/7101771.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_7101771
loop_
_publ_author_name
'Maeda, Hiromitsu'
'Ito, Yoshihiro'
'Kusunose, Yukio'
'Nakanishi, Takashi'
_publ_section_title
;
 Di-pyrrolyl-pyrazoles: anion receptors in protonated form and
 efficient building blocks for organized structures.
;
_journal_issue                   11
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1136
_journal_page_last               1138
_journal_paper_doi               10.1039/b615787d
_journal_year                    2007
_chemical_formula_moiety         'C11 H11 N4, C2 F3 O2'
_chemical_formula_sum            'C13 H11 F3 N4 O2'
_chemical_formula_weight         312.26
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 91.1800(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3569(10)
_cell_length_b                   15.2520(11)
_cell_length_c                   6.0571(4)
_cell_measurement_reflns_used    4748
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.88
_cell_measurement_theta_min      2.67
_cell_volume                     1326.05(16)
_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      120(2)
_diffrn_detector_area_resol_mean 8.366
_diffrn_measured_fraction_theta_full 0.928
_diffrn_measured_fraction_theta_max 0.928
_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  0.0175
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            8027
_diffrn_reflns_theta_full        28.19
_diffrn_reflns_theta_max         28.19
_diffrn_reflns_theta_min         1.42
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.133
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0411
_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)+(0.0639P)²+0.4490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1228
_reflns_number_gt                2638
_reflns_number_total             3018
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b615787d.txt
_cod_data_source_block           dpp
_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 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7101771
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
C1 C 0.21219(12) 0.17754(10) 0.8187(3) 0.0254(3) Uani 1 1 d .
H1 H 0.1694 0.2084 0.9075 0.031 Uiso 1 1 calc R
C2 C 0.30659(12) 0.17307(10) 0.8544(3) 0.0255(3) Uani 1 1 d .
H2 H 0.3409 0.2001 0.9716 0.031 Uiso 1 1 calc R
C3 C 0.34331(11) 0.12093(10) 0.6848(2) 0.0232(3) Uani 1 1 d .
H3 H 0.4070 0.1063 0.6665 0.028 Uiso 1 1 calc R
C4 C 0.26948(10) 0.09512(10) 0.5502(2) 0.0187(3) Uani 1 1 d .
C5 C 0.27052(10) 0.04257(9) 0.3519(2) 0.0181(3) Uani 1 1 d .
C6 C 0.34444(10) -0.00132(10) 0.2566(2) 0.0196(3) Uani 1 1 d .
H6 H 0.4069 -0.0037 0.3115 0.023 Uiso 1 1 calc R
C7 C 0.30945(10) -0.04104(9) 0.0653(2) 0.0181(3) Uani 1 1 d .
C8 C 0.35766(10) -0.09400(10) -0.0937(2) 0.0187(3) Uani 1 1 d .
C9 C 0.45113(11) -0.11430(10) -0.1001(3) 0.0226(3) Uani 1 1 d .
H9 H 0.4981 -0.0954 0.0020 0.027 Uiso 1 1 calc R
C10 C 0.46423(11) -0.16812(10) -0.2859(3) 0.0246(3) Uani 1 1 d .
H10A H 0.5216 -0.1924 -0.3320 0.029 Uiso 1 1 calc R
C11 C 0.37876(11) -0.17898(10) -0.3879(3) 0.0231(3) Uani 1 1 d .
H11A H 0.3666 -0.2122 -0.5180 0.028 Uiso 1 1 calc R
C12 C 0.06687(11) 0.83842(11) 0.3833(3) 0.0236(3) Uani 1 1 d .
C13 C 0.05188(10) 0.89393(9) 0.5948(2) 0.0189(3) Uani 1 1 d .
F1 F 0.15459(8) 0.81389(8) 0.35715(19) 0.0455(3) Uani 1 1 d .
F2 F 0.01387(8) 0.76652(7) 0.38209(16) 0.0365(3) Uani 1 1 d .
F3 F 0.04182(7) 0.88442(7) 0.20324(15) 0.0331(3) Uani 1 1 d .
N1 N 0.19004(9) 0.13017(8) 0.6343(2) 0.0218(3) Uani 1 1 d .
H1N H 0.1335 0.1232 0.5781 0.026 Uiso 1 1 calc R
N2 N 0.19458(9) 0.02869(8) 0.22247(19) 0.0185(3) Uani 1 1 d .
H2N H 0.1385 0.0493 0.2467 0.022 Uiso 1 1 calc R
N3 N 0.21827(8) -0.02209(8) 0.0492(2) 0.0188(3) Uani 1 1 d .
H3N H 0.1800 -0.0398 -0.0571 0.023 Uiso 1 1 calc R
N4 N 0.31431(9) -0.13399(8) -0.2710(2) 0.0204(3) Uani 1 1 d .
H4N H 0.2544 -0.1310 -0.3039 0.024 Uiso 1 1 calc R
O1 O 0.12373(7) 0.91708(8) 0.69497(18) 0.0253(3) Uani 1 1 d .
O2 O -0.03088(7) 0.90860(8) 0.63279(18) 0.0248(3) 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'
F F 0.0171 0.0103 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C2 108.45(14)
N1 C1 H1 125.8
C2 C1 H1 125.8
C1 C2 C3 107.27(14)
C1 C2 H2 126.4
C3 C2 H2 126.4
C4 C3 C2 107.26(14)
C4 C3 H3 126.4
C2 C3 H3 126.4
N1 C4 C3 107.74(13)
N1 C4 C5 123.34(13)
C3 C4 C5 128.91(14)
N2 C5 C6 107.37(13)
N2 C5 C4 123.32(13)
C6 C5 C4 129.31(13)
C5 C6 C7 106.83(13)
C5 C6 H6 126.6
C7 C6 H6 126.6
N3 C7 C6 107.57(13)
N3 C7 C8 123.48(13)
C6 C7 C8 128.95(13)
N4 C8 C9 107.69(13)
N4 C8 C7 123.67(13)
C9 C8 C7 128.64(14)
C8 C9 C10 107.43(13)
C8 C9 H9 126.3
C10 C9 H9 126.3
C11 C10 C9 107.29(14)
C11 C10 H10A 126.4
C9 C10 H10A 126.4
N4 C11 C10 108.40(14)
N4 C11 H11A 125.8
C10 C11 H11A 125.8
F1 C12 F2 108.07(14)
F1 C12 F3 106.88(13)
F2 C12 F3 106.41(12)
F1 C12 C13 113.57(13)
F2 C12 C13 111.30(12)
F3 C12 C13 110.26(12)
O2 C13 O1 130.72(14)
O2 C13 C12 113.71(13)
O1 C13 C12 115.56(13)
C1 N1 C4 109.28(13)
C1 N1 H1N 125.4
C4 N1 H1N 125.4
C5 N2 N3 109.15(12)
C5 N2 H2N 125.4
N3 N2 H2N 125.4
C7 N3 N2 109.08(12)
C7 N3 H3N 125.5
N2 N3 H3N 125.5
C11 N4 C8 109.19(13)
C11 N4 H4N 125.4
C8 N4 H4N 125.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.3623(19)
C1 C2 1.370(2)
C1 H1 0.9500
C2 C3 1.410(2)
C2 H2 0.9500
C3 C4 1.381(2)
C3 H3 0.9500
C4 N1 1.3674(19)
C4 C5 1.445(2)
C5 N2 1.3463(18)
C5 C6 1.390(2)
C6 C7 1.392(2)
C6 H6 0.9500
C7 N3 1.3422(19)
C7 C8 1.445(2)
C8 N4 1.3730(19)
C8 C9 1.379(2)
C9 C10 1.408(2)
C9 H9 0.9500
C10 C11 1.373(2)
C10 H10A 0.9500
C11 N4 1.3621(19)
C11 H11A 0.9500
C12 F1 1.3263(19)
C12 F2 1.3346(19)
C12 F3 1.3395(18)
C12 C13 1.554(2)
C13 O2 1.2354(18)
C13 O1 1.2373(18)
N1 H1N 0.8800
N2 N3 1.3535(17)
N2 H2N 0.8800
N3 H3N 0.8800
N4 H4N 0.8800
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652996
