#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:38:36 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180271 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/57/7115704.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_7115704
loop_
_publ_author_name
'Murat K. Deliomeroglu'
'Vincent M. Lynch'
'Jonathan L. Sessler'
_publ_section_title
;
 Conformationally switchable non-cyclic tetrapyrrole receptors: synthesis
 of tetrakis(1H-pyrrole-2-carbaldehyde) derivatives and their anion
 binding properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              11863
_journal_paper_doi               10.1039/C4cc05093B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C17 H13 N3 O'
_chemical_formula_sum            'C17 H13 N3 O'
_chemical_formula_weight         275.30
_chemical_name_systematic
; 
 ? 
;
_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                 124.13(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.916(5)
_cell_length_b                   4.6430(12)
_cell_length_c                   20.248(12)
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.25
_cell_volume                     1394.2(11)
_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      298(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0652
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3836
_diffrn_reflns_theta_full        28.97
_diffrn_reflns_theta_max         28.97
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             576.0
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.362
_refine_ls_R_factor_all          0.1839
_refine_ls_R_factor_gt           0.0969
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0100P)²+0.6710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1715
_reflns_number_gt                2136
_reflns_number_total             3664
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05093b2.cif
_cod_data_source_block           L
_cod_original_cell_volume        1394.2(10)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7115704
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
O1 O 0.3368(3) 0.8468(11) 0.0315(3) 0.0897(16) Uani 1 1 d .
N3 N 0.3165(5) 0.0451(12) 0.2901(5) 0.118(2) Uani 1 1 d .
N2 N 0.2844(3) 0.3744(10) 0.1595(3) 0.0749(16) Uani 1 1 d .
N1 N 0.2797(4) 0.5534(10) 0.1014(3) 0.0746(16) Uani 1 1 d .
C14 C 0.4644(4) -0.0076(13) 0.3197(5) 0.075(2) Uani 1 1 d .
H14 H 0.5069 0.0348 0.3086 0.090 Uiso 1 1 calc R
C17 C 0.3410(5) -0.1345(14) 0.3548(5) 0.094(2) Uani 1 1 d .
H17 H 0.2999 -0.1780 0.3677 0.113 Uiso 1 1 calc R
C16 C 0.4260(5) -0.2440(14) 0.3985(5) 0.114(3) Uani 1 1 d .
H16 H 0.4441 -0.3653 0.4416 0.137 Uiso 1 1 calc R
C11 C 0.2002(4) 0.6562(11) 0.0507(4) 0.0668(17) Uani 1 1 d .
H11 H 0.1532 0.6022 0.0552 0.080 Uiso 1 1 calc R
C13 C 0.3854(4) 0.0982(12) 0.2769(4) 0.0705(18) Uani 1 1 d .
C4 C 0.1533(5) 1.2590(12) -0.1264(4) 0.079(2) Uani 1 1 d .
H4 H 0.1451 1.3974 -0.1631 0.095 Uiso 1 1 calc R
C15 C 0.4847(5) -0.1714(18) 0.3777(6) 0.128(4) Uani 1 1 d .
H15 H 0.5427 -0.2469 0.4080 0.154 Uiso 1 1 calc R
C5 C -0.0080(5) 1.2876(12) -0.1783(4) 0.0792(19) Uani 1 1 d .
H5 H -0.0165 1.4243 -0.2155 0.095 Uiso 1 1 calc R
C2 C 0.2511(5) 0.9448(12) -0.0182(4) 0.072(2) Uani 1 1 d .
C1 C 0.1812(4) 0.8499(10) -0.0122(4) 0.0568(15) Uani 1 1 d .
C9 C 0.0932(4) 0.9634(10) -0.0669(4) 0.0566(15) Uani 1 1 d .
C12 C 0.3645(4) 0.2819(12) 0.2108(4) 0.076(2) Uani 1 1 d .
H12 H 0.4108 0.3350 0.2053 0.092 Uiso 1 1 calc R
C7 C -0.0667(5) 0.9901(14) -0.1214(5) 0.085(2) Uani 1 1 d .
H7 H -0.1156 0.9260 -0.1211 0.102 Uiso 1 1 calc R
C3 C 0.2357(5) 1.1429(13) -0.0753(5) 0.082(2) Uani 1 1 d .
H3 H 0.2833 1.1982 -0.0788 0.098 Uiso 1 1 calc R
C10 C 0.0792(4) 1.1688(11) -0.1238(4) 0.0667(18) Uani 1 1 d .
C8 C 0.0178(4) 0.8759(12) -0.0679(4) 0.078(2) Uani 1 1 d .
H8 H 0.0248 0.7375 -0.0316 0.094 Uiso 1 1 calc R
C6 C -0.0794(5) 1.2001(14) -0.1759(5) 0.089(2) Uani 1 1 d .
H6 H -0.1362 1.2806 -0.2104 0.106 Uiso 1 1 calc R
H1O H 0.332(6) 0.714(16) 0.056(6) 0.17(4) Uiso 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 O1 H1O 104(6)
C17 N3 C13 115.4(6)
C12 N2 N1 113.0(5)
C11 N1 N2 113.9(5)
C15 C14 C13 119.6(6)
C15 C14 H14 120.2
C13 C14 H14 120.2
C16 C17 N3 118.8(6)
C16 C17 H17 120.6
N3 C17 H17 120.6
C17 C16 C15 118.5(7)
C17 C16 H16 120.7
C15 C16 H16 120.7
N1 C11 C1 122.9(5)
N1 C11 H11 118.6
C1 C11 H11 118.6
C14 C13 N3 123.7(6)
C14 C13 C12 118.0(6)
N3 C13 C12 118.2(6)
C3 C4 C10 119.8(6)
C3 C4 H4 120.1
C10 C4 H4 120.1
C14 C15 C16 124.0(7)
C14 C15 H15 118.0
C16 C15 H15 118.0
C6 C5 C10 119.9(6)
C6 C5 H5 120.1
C10 C5 H5 120.1
O1 C2 C3 117.2(6)
O1 C2 C1 121.7(6)
C3 C2 C1 121.1(6)
C2 C1 C9 118.0(5)
C2 C1 C11 119.9(5)
C9 C1 C11 122.0(5)
C8 C9 C10 117.2(6)
C8 C9 C1 122.7(5)
C10 C9 C1 120.0(5)
N2 C12 C13 122.5(5)
N2 C12 H12 118.7
C13 C12 H12 118.7
C8 C7 C6 120.8(6)
C8 C7 H7 119.6
C6 C7 H7 119.6
C4 C3 C2 121.8(6)
C4 C3 H3 119.1
C2 C3 H3 119.1
C9 C10 C4 119.2(6)
C9 C10 C5 120.9(5)
C4 C10 C5 119.9(6)
C7 C8 C9 121.6(6)
C7 C8 H8 119.2
C9 C8 H8 119.2
C5 C6 C7 119.7(7)
C5 C6 H6 120.2
C7 C6 H6 120.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C2 1.357(7)
O1 H1O 0.82(8)
N3 C17 1.400(9)
N3 C13 1.424(6)
N2 C12 1.284(7)
N2 N1 1.404(6)
N1 C11 1.293(7)
C14 C15 1.269(9)
C14 C13 1.271(8)
C14 H14 0.9300
C17 C16 1.360(8)
C17 H17 0.9300
C16 C15 1.377(8)
C16 H16 0.9300
C11 C1 1.435(7)
C11 H11 0.9300
C13 C12 1.448(8)
C4 C3 1.352(8)
C4 C10 1.421(6)
C4 H4 0.9300
C15 H15 0.9300
C5 C6 1.369(7)
C5 C10 1.424(8)
C5 H5 0.9300
C2 C3 1.378(8)
C2 C1 1.397(6)
C1 C9 1.425(7)
C9 C8 1.401(6)
C9 C10 1.404(7)
C12 H12 0.9300
C7 C8 1.380(8)
C7 C6 1.391(8)
C7 H7 0.9300
C3 H3 0.9300
C8 H8 0.9300
C6 H6 0.9300
