#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/37/7053700.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7053700
loop_
_publ_author_name
'Dehaen, Wim'
'Gale, Philip A.'
'García-Garrido, Sergio E.'
'Kostermans, Maarten'
'Light, Mark E.'
_publ_section_title
;
 Anion recognition by N-confused calix[4]pyrrole-α-carbaldehyde and its
 Knoevenagel reaction derivatives
;
_journal_issue                   5
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              691
_journal_paper_doi               10.1039/b616467f
_journal_volume                  31
_journal_year                    2007
_chemical_formula_sum            'C29 H37.8 N4 O1.9'
_chemical_formula_weight         472.83
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                107.535(2)
_cell_angle_beta                 92.714(2)
_cell_angle_gamma                91.380(2)
_cell_formula_units_Z            2
_cell_length_a                   10.1714(3)
_cell_length_b                   10.1756(3)
_cell_length_c                   13.1069(4)
_cell_measurement_reflns_used    5845
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     1291.03(7)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29203
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9598
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Dark Yellow'
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             510
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5888
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0693
_refine_ls_shift/su_max          0.029
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0979P)²+1.6184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1779
_refine_ls_wR_factor_ref         0.2009
_reflns_number_gt                3951
_reflns_number_total             5888
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b616467fsup1.cif
_cod_data_source_block           2006sot0648
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C29 H37.80 N4 O1.90'
_cod_database_code               7053700
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O2 O 0.71001(4) 0.31185(4) 0.46614(3) 0.04577(12) Uani 0.90 1 d PD . .
H99 H 0.72871(18) 0.22509(13) 0.4620(3) 0.050 Uiso 0.90 1 d PD . .
H98 H 0.62128(12) 0.3061(2) 0.4557(2) 0.050 Uiso 0.90 1 d PD . .
C1 C 0.32505(3) 0.21712(4) 0.17128(3) 0.02298(10) Uani 1 1 d . . .
C2 C 0.30311(4) 0.12898(4) 0.06904(3) 0.03054(12) Uani 1 1 d . . .
H2 H 0.2676 0.1526 0.0088 0.037 Uiso 1 1 calc R . .
C3 C 0.34293(4) -0.00366(4) 0.06939(3) 0.03105(12) Uani 1 1 d . . .
H3 H 0.3380 -0.0848 0.0096 0.037 Uiso 1 1 calc R . .
C4 C 0.38957(3) 0.00603(4) 0.17104(3) 0.02212(10) Uani 1 1 d . . .
C5 C 0.43954(4) -0.10178(4) 0.21974(3) 0.02527(11) Uani 1 1 d . . .
C6 C 0.34151(4) -0.12400(4) 0.29967(3) 0.03501(12) Uani 1 1 d . . .
H6A H 0.3338 -0.0374 0.3573 0.053 Uiso 1 1 calc R . .
H6B H 0.3733 -0.1950 0.3302 0.053 Uiso 1 1 calc R . .
H6C H 0.2551 -0.1537 0.2624 0.053 Uiso 1 1 calc R . .
C7 C 0.45238(4) -0.23836(4) 0.13055(4) 0.03554(13) Uani 1 1 d . . .
H7A H 0.3662 -0.2687 0.0929 0.053 Uiso 1 1 calc R . .
H7B H 0.4839 -0.3086 0.1621 0.053 Uiso 1 1 calc R . .
H7C H 0.5152 -0.2250 0.0798 0.053 Uiso 1 1 calc R . .
C8 C 0.57321(4) -0.05650(3) 0.27878(3) 0.02269(10) Uani 1 1 d . . .
C9 C 0.61867(4) -0.05412(4) 0.37897(3) 0.02915(11) Uani 1 1 d . . .
H9 H 0.5687 -0.0766 0.4312 0.035 Uiso 1 1 calc R . .
C10 C 0.75469(4) -0.01181(4) 0.39119(3) 0.02923(11) Uani 1 1 d . . .
H10 H 0.8113 -0.0015 0.4531 0.035 Uiso 1 1 calc R . .
C11 C 0.78934(3) 0.01126(3) 0.29860(3) 0.02177(10) Uani 1 1 d . . .
C12 C 0.91996(3) 0.05469(4) 0.26388(3) 0.02279(10) Uani 1 1 d . . .
C13 C 0.97895(4) -0.07000(4) 0.18358(3) 0.02961(12) Uani 1 1 d . . .
H13A H 0.9946 -0.1420 0.2178 0.044 Uiso 1 1 calc R . .
H13B H 1.0624 -0.0412 0.1609 0.044 Uiso 1 1 calc R . .
H13C H 0.9173 -0.1062 0.1210 0.044 Uiso 1 1 calc R . .
C14 C 1.01757(4) 0.10501(4) 0.36265(3) 0.03191(12) Uani 1 1 d . . .
H14A H 0.9844 0.1873 0.4137 0.048 Uiso 1 1 calc R . .
H14B H 1.1035 0.1277 0.3401 0.048 Uiso 1 1 calc R . .
H14C H 1.0269 0.0321 0.3968 0.048 Uiso 1 1 calc R . .
C15 C 0.90006(3) 0.16733(4) 0.21246(3) 0.02129(10) Uani 1 1 d . . .
C16 C 0.92895(4) 0.17629(4) 0.11381(3) 0.02543(11) Uani 1 1 d . . .
H16 H 0.9664 0.1065 0.0586 0.031 Uiso 1 1 calc R . .
C17 C 0.89310(4) 0.30842(4) 0.10829(3) 0.02539(11) Uani 1 1 d . . .
H17 H 0.9017 0.3424 0.0488 0.030 Uiso 1 1 calc R . .
C18 C 0.84399(3) 0.37765(3) 0.20437(3) 0.02090(10) Uani 1 1 d . . .
C19 C 0.79416(4) 0.52225(4) 0.24634(3) 0.02451(10) Uani 1 1 d . A .
C20 C 0.79081(4) 0.59106(4) 0.15663(4) 0.03720(12) Uani 1 1 d . . .
H20A H 0.7563 0.6835 0.1835 0.056 Uiso 1 1 calc R . .
H20B H 0.7338 0.5354 0.0958 0.056 Uiso 1 1 calc R . .
H20C H 0.8802 0.5981 0.1334 0.056 Uiso 1 1 calc R . .
C21 C 0.88969(4) 0.60834(4) 0.33843(4) 0.03652(14) Uani 1 1 d . . .
H21A H 0.8618 0.7038 0.3624 0.055 Uiso 1 1 calc R . .
H21B H 0.9789 0.6065 0.3131 0.055 Uiso 1 1 calc R . .
H21C H 0.8890 0.5694 0.3983 0.055 Uiso 1 1 calc R . .
C22 C 0.65297(4) 0.51291(3) 0.28134(3) 0.02225(10) Uani 1 1 d D . .
C23A C 0.59247(3) 0.58333(3) 0.36980(3) 0.02500(12) Uani 0.90 1 d PD A 1
C26A C 0.63102(4) 0.67908(5) 0.46393(3) 0.03625(14) Uani 0.90 1 d PD A 1
H26A H 0.7201 0.7127 0.4725 0.044 Uiso 0.90 1 calc PR A 1
O1A O 0.55714(4) 0.72877(4) 0.54313(3) 0.04665(12) Uani 0.90 1 d PD A 1
N4A N 0.45966(3) 0.53782(3) 0.35557(2) 0.02915(10) Uani 0.90 1 d PD A 1
H4A H 0.3995 0.5695 0.4019 0.035 Uiso 0.90 1 calc PR A 1
C23B C 0.45966(3) 0.53782(3) 0.35557(2) 0.02500(12) Uani 0.10 1 d PD A 2
C26B C 0.39521(7) 0.56610(10) 0.44767(4) 0.03625(14) Uani 0.10 1 d PD . 2
H26B H 0.3203 0.5142 0.4569 0.044 Uiso 0.10 1 calc PRD . 2
O1B O 0.44683(19) 0.66993(13) 0.51997(12) 0.04665(12) Uani 0.10 1 d PD . 2
N4B N 0.59247(3) 0.58333(3) 0.36980(3) 0.02915(10) Uani 0.10 1 d PD A 2
H4B H 0.6296 0.6463 0.4261 0.035 Uiso 0.10 1 calc PR A 2
C24 C 0.43769(4) 0.44105(4) 0.26318(3) 0.02454(10) Uani 1 1 d D . .
C25 C 0.55625(4) 0.42078(4) 0.21219(3) 0.02426(10) Uani 1 1 d . A .
H25 H 0.5699 0.3573 0.1440 0.029 Uiso 1 1 calc R . .
C27 C 0.30552(4) 0.36984(4) 0.21764(3) 0.02643(11) Uani 1 1 d . A .
C28 C 0.25482(4) 0.42766(4) 0.12768(4) 0.03824(13) Uani 1 1 d . . .
H28A H 0.3196 0.4129 0.0727 0.057 Uiso 1 1 calc R A .
H28B H 0.2416 0.5267 0.1576 0.057 Uiso 1 1 calc R . .
H28C H 0.1710 0.3802 0.0955 0.057 Uiso 1 1 calc R . .
C29 C 0.20317(4) 0.39677(4) 0.30319(3) 0.03280(12) Uani 1 1 d . . .
H29A H 0.1173 0.3564 0.2698 0.049 Uiso 1 1 calc R A .
H29B H 0.1964 0.4964 0.3358 0.049 Uiso 1 1 calc RD . .
H29C H 0.2304 0.3547 0.3586 0.049 Uiso 1 1 calc RD . .
N1 N 0.37778(3) 0.14052(3) 0.23259(2) 0.02182(8) Uani 1 1 d . . .
H1 H 0.4007 0.1731 0.3014 0.026 Uiso 1 1 calc R . .
N2 N 0.67799(3) -0.01675(3) 0.23032(2) 0.02220(9) Uani 1 1 d . . .
H2A H 0.6743 -0.0102 0.1648 0.027 Uiso 1 1 calc R . .
N3 N 0.84866(3) 0.29187(3) 0.26742(2) 0.02173(8) Uani 1 1 d . . .
H3A H 0.8227 0.3129 0.3333 0.026 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'
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
O1B O2 C26B 42.89(5) 2_666 2_666
C2 C1 N1 106.74(3) . .
C2 C1 C27 131.47(4) . .
N1 C1 C27 121.75(3) . .
C1 C2 C3 107.84(4) . .
C4 C3 C2 107.87(3) . .
C3 C4 N1 107.14(3) . .
C3 C4 C5 131.50(3) . .
N1 C4 C5 121.28(3) . .
C4 C5 C8 110.80(3) . .
C4 C5 C7 109.36(3) . .
C8 C5 C7 109.15(3) . .
C4 C5 C6 109.58(3) . .
C8 C5 C6 108.78(3) . .
C7 C5 C6 109.14(3) . .
C9 C8 N2 106.82(3) . .
C9 C8 C5 130.95(4) . .
N2 C8 C5 122.10(3) . .
C8 C9 C10 107.77(4) . .
C11 C10 C9 108.14(3) . .
C10 C11 N2 106.62(3) . .
C10 C11 C12 132.05(3) . .
N2 C11 C12 121.31(3) . .
C15 C12 C11 110.26(3) . .
C15 C12 C13 109.50(3) . .
C11 C12 C13 109.83(3) . .
C15 C12 C14 110.40(3) . .
C11 C12 C14 109.07(3) . .
C13 C12 C14 107.74(3) . .
C16 C15 N3 106.74(3) . .
C16 C15 C12 131.65(3) . .
N3 C15 C12 121.57(3) . .
C15 C16 C17 108.09(3) . .
C18 C17 C16 107.50(4) . .
C17 C18 N3 107.46(3) . .
C17 C18 C19 131.56(4) . .
N3 C18 C19 120.95(3) . .
C18 C19 C22 108.79(3) . .
C18 C19 C20 109.74(3) . .
C22 C19 C20 108.30(3) . .
C18 C19 C21 108.96(3) . .
C22 C19 C21 112.77(3) . .
C20 C19 C21 108.24(3) . .
C23A C22 C25 107.04(3) . .
C23A C22 C19 132.28(3) . .
C25 C22 C19 120.61(3) . .
C22 C23A C26A 135.37(4) . .
C22 C23A N4A 107.52(3) . .
C26A C23A N4A 117.08(3) . .
O1A C26A C23A 125.72(4) . .
C24 N4A C23A 110.47(3) . .
O1B C26B O2 60.43(9) . 2_666
C26B O1B O2 76.69(10) . 2_666
N4A C24 C25 107.72(3) . .
N4A C24 C27 126.07(3) . .
C25 C24 C27 126.14(3) . .
C24 C25 C22 107.25(3) . .
C1 C27 C24 108.55(3) . .
C1 C27 C29 110.71(3) . .
C24 C27 C29 111.62(3) . .
C1 C27 C28 109.32(3) . .
C24 C27 C28 108.42(3) . .
C29 C27 C28 108.17(3) . .
C4 N1 C1 110.41(3) . .
C11 N2 C8 110.65(3) . .
C18 N3 C15 110.20(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 O1B 1.623(2) 2_666
O2 C26B 1.8158(8) 2_666
C1 C2 1.3739(5) .
C1 N1 1.3776(5) .
C1 C27 1.5103(5) .
C2 C3 1.4197(6) .
C3 C4 1.3669(6) .
C4 N1 1.3747(4) .
C4 C5 1.5124(6) .
C5 C8 1.5215(5) .
C5 C7 1.5360(5) .
C5 C6 1.5406(6) .
C8 C9 1.3644(6) .
C8 N2 1.3787(5) .
C9 C10 1.4262(6) .
C10 C11 1.3639(6) .
C11 N2 1.3783(5) .
C11 C12 1.5223(5) .
C12 C15 1.5075(6) .
C12 C13 1.5393(5) .
C12 C14 1.5422(5) .
C15 C16 1.3683(6) .
C15 N3 1.3841(4) .
C16 C17 1.4233(6) .
C17 C18 1.3688(5) .
C18 N3 1.3711(5) .
C18 C19 1.5163(5) .
C19 C22 1.5375(5) .
C19 C20 1.5386(7) .
C19 C21 1.5424(5) .
C22 C23A 1.3507(5) .
C22 C25 1.4239(5) .
C23A C26A 1.3553(5) .
C23A N4A 1.4029(5) .
C26A O1A 1.2937(5) .
N4A C24 1.3158(4) .
C26B O1B 1.2699(14) .
C26B O2 1.8158(8) 2_666
O1B O2 1.623(2) 2_666
C24 C25 1.3960(5) .
C24 C27 1.5182(5) .
C27 C29 1.5346(6) .
C27 C28 1.5418(7) .
