#------------------------------------------------------------------------------
#$Date: 2016-03-24 00:09:19 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179525 $
#$URL: svn://www.crystallography.net/cod/cif/4/34/22/4342232.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_4342232
loop_
_publ_author_name
'Sommer, Samantha K.'
'Zakharov, Lev N.'
'Pluth, Michael D.'
_publ_section_title
;
 Design, Synthesis, and Characterization of Hybrid Metal-Ligand
 Hydrogen-Bonded (MLHB) Supramolecular Architectures.
;
_journal_issue                   4
_journal_name_full               'Inorganic chemistry'
_journal_page_first              1912
_journal_page_last               1918
_journal_paper_doi               10.1021/ic502802f
_journal_volume                  54
_journal_year                    2015
_chemical_formula_sum            'C21 H16 N O P'
_chemical_formula_weight         329.32
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                115.602(4)
_cell_angle_beta                 96.827(4)
_cell_angle_gamma                93.940(4)
_cell_formula_units_Z            2
_cell_length_a                   8.866(2)
_cell_length_b                   9.850(3)
_cell_length_c                   10.991(3)
_cell_measurement_reflns_used    2868
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     851.7(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Apex 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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8308
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.08
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  0.9802
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3003
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0651
_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)+(0.0546P)²+1.2729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1480
_reflns_number_gt                2899
_reflns_number_total             3003
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic502802f_si_002.cif
_cod_data_source_block           mplu4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4342231--4342233.cif.
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4342232
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
P1 P 0.42353(9) 0.83791(8) 0.26234(7) 0.0313(2) Uani 1 1 d
O1 O 0.0528(2) 0.3388(3) 0.5208(3) 0.0464(6) Uani 1 1 d
N1 N 0.1811(3) 0.4789(3) 0.4384(3) 0.0322(6) Uani 1 1 d
C1 C 0.1624(3) 0.3572(3) 0.4658(3) 0.0340(7) Uani 1 1 d
C2 C 0.2755(3) 0.2533(3) 0.4251(3) 0.0364(7) Uani 1 1 d
C3 C 0.3885(3) 0.2772(3) 0.3632(3) 0.0346(7) Uani 1 1 d
C4 C 0.4042(3) 0.4061(3) 0.3348(3) 0.0310(6) Uani 1 1 d
C5 C 0.2951(3) 0.5078(3) 0.3741(3) 0.0292(6) Uani 1 1 d
C6 C 0.3037(3) 0.6358(3) 0.3506(3) 0.0307(6) Uani 1 1 d
C7 C 0.4195(3) 0.6646(3) 0.2868(3) 0.0311(6) Uani 1 1 d
C8 C 0.5288(4) 0.5632(3) 0.2477(3) 0.0365(7) Uani 1 1 d
C9 C 0.5207(3) 0.4377(3) 0.2717(3) 0.0356(7) Uani 1 1 d
C10 C 0.6193(3) 0.8607(3) 0.2301(3) 0.0336(6) Uani 1 1 d
C11 C 0.6668(4) 0.7820(4) 0.1045(4) 0.0462(8) Uani 1 1 d
C12 C 0.8188(5) 0.7989(5) 0.0927(5) 0.0622(11) Uani 1 1 d
C13 C 0.9263(5) 0.8945(5) 0.2044(6) 0.0692(14) Uani 1 1 d
C14 C 0.8804(5) 0.9750(5) 0.3278(6) 0.0645(12) Uani 1 1 d
C15 C 0.7284(4) 0.9596(4) 0.3416(4) 0.0436(8) Uani 1 1 d
C16 C 0.3093(3) 0.7699(3) 0.0918(3) 0.0325(6) Uani 1 1 d
C17 C 0.3021(4) 0.8741(4) 0.0368(3) 0.0470(8) Uani 1 1 d
C18 C 0.2116(5) 0.8350(5) -0.0875(4) 0.0572(10) Uani 1 1 d
C19 C 0.1257(4) 0.6933(5) -0.1584(4) 0.0554(10) Uani 1 1 d
C20 C 0.1319(4) 0.5902(4) -0.1049(4) 0.0501(9) Uani 1 1 d
C21 C 0.2232(3) 0.6285(4) 0.0193(3) 0.0382(7) Uani 1 1 d
H1N H 0.120(3) 0.541(3) 0.457(3) 0.022(7) Uiso 1 1 d
H2 H 0.265(4) 0.170(4) 0.446(3) 0.049(9) Uiso 1 1 d
H3 H 0.461(3) 0.211(3) 0.339(3) 0.029(8) Uiso 1 1 d
H6 H 0.231(3) 0.700(3) 0.379(3) 0.025(7) Uiso 1 1 d
H8 H 0.608(4) 0.584(3) 0.205(3) 0.039(8) Uiso 1 1 d
H9 H 0.594(3) 0.370(3) 0.248(3) 0.030(7) Uiso 1 1 d
H11 H 0.590(4) 0.715(5) 0.029(4) 0.065(12) Uiso 1 1 d
H12 H 0.842(5) 0.745(5) 0.008(5) 0.085(15) Uiso 1 1 d
H13 H 1.025(6) 0.905(5) 0.198(5) 0.085(14) Uiso 1 1 d
H14 H 0.942(5) 1.039(5) 0.399(4) 0.068(13) Uiso 1 1 d
H15 H 0.695(4) 1.018(4) 0.429(4) 0.051(10) Uiso 1 1 d
H17 H 0.359(4) 0.972(4) 0.088(4) 0.051(10) Uiso 1 1 d
H18 H 0.206(5) 0.901(5) -0.123(5) 0.079(14) Uiso 1 1 d
H19 H 0.063(4) 0.671(4) -0.243(4) 0.064(11) Uiso 1 1 d
H20 H 0.075(4) 0.496(4) -0.155(4) 0.053(10) Uiso 1 1 d
H21 H 0.229(3) 0.561(3) 0.058(3) 0.031(8) 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'
P P 0.1023 0.0942 '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
C10 P1 C16 102.50(13)
C10 P1 C7 101.68(13)
C16 P1 C7 102.43(13)
C1 N1 C5 125.4(3)
C1 N1 H1N 121(2)
C5 N1 H1N 114(2)
O1 C1 N1 120.5(3)
O1 C1 C2 123.9(3)
N1 C1 C2 115.6(3)
C3 C2 C1 121.1(3)
C3 C2 H2 123(2)
C1 C2 H2 116(2)
C2 C3 C4 121.9(3)
C2 C3 H3 120.0(18)
C4 C3 H3 118.1(18)
C9 C4 C5 118.1(3)
C9 C4 C3 124.4(3)
C5 C4 C3 117.5(3)
N1 C5 C6 120.8(3)
N1 C5 C4 118.5(2)
C6 C5 C4 120.7(3)
C7 C6 C5 120.4(3)
C7 C6 H6 122.0(17)
C5 C6 H6 117.6(17)
C6 C7 C8 119.0(3)
C6 C7 P1 117.4(2)
C8 C7 P1 123.6(2)
C9 C8 C7 120.5(3)
C9 C8 H8 120.8(19)
C7 C8 H8 118.8(19)
C8 C9 C4 121.4(3)
C8 C9 H9 121.7(18)
C4 C9 H9 116.9(18)
C15 C10 C11 118.5(3)
C15 C10 P1 116.8(2)
C11 C10 P1 124.6(2)
C12 C11 C10 120.3(4)
C12 C11 H11 122(2)
C10 C11 H11 117(2)
C11 C12 C13 120.7(4)
C11 C12 H12 116(3)
C13 C12 H12 124(3)
C14 C13 C12 119.5(4)
C14 C13 H13 119(3)
C12 C13 H13 122(3)
C13 C14 C15 120.6(4)
C13 C14 H14 123(3)
C15 C14 H14 117(3)
C14 C15 C10 120.3(4)
C14 C15 H15 121(2)
C10 C15 H15 119(2)
C21 C16 C17 118.5(3)
C21 C16 P1 124.7(2)
C17 C16 P1 116.6(2)
C18 C17 C16 120.3(3)
C18 C17 H17 121(2)
C16 C17 H17 119(2)
C17 C18 C19 120.4(4)
C17 C18 H18 121(3)
C19 C18 H18 119(3)
C20 C19 C18 119.6(3)
C20 C19 H19 122(2)
C18 C19 H19 118(2)
C19 C20 C21 120.2(3)
C19 C20 H20 118(2)
C21 C20 H20 122(2)
C16 C21 C20 120.9(3)
C16 C21 H21 117.5(18)
C20 C21 H21 121.5(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C10 1.830(3)
P1 C16 1.833(3)
P1 C7 1.838(3)
O1 C1 1.245(4)
N1 C1 1.361(4)
N1 C5 1.381(4)
N1 H1N 0.82(3)
C1 C2 1.450(4)
C2 C3 1.338(4)
C2 H2 0.94(4)
C3 C4 1.434(4)
C3 H3 0.92(3)
C4 C9 1.399(4)
C4 C5 1.409(4)
C5 C6 1.392(4)
C6 C7 1.389(4)
C6 H6 0.92(3)
C7 C8 1.408(4)
C8 C9 1.370(4)
C8 H8 0.95(3)
C9 H9 0.94(3)
C10 C15 1.393(4)
C10 C11 1.394(5)
C11 C12 1.375(5)
C11 H11 0.96(4)
C12 C13 1.378(7)
C12 H12 0.90(5)
C13 C14 1.372(7)
C13 H13 0.89(5)
C14 C15 1.379(5)
C14 H14 0.86(4)
C15 H15 0.97(4)
C16 C21 1.381(4)
C16 C17 1.399(4)
C17 C18 1.379(5)
C17 H17 0.95(4)
C18 C19 1.381(6)
C18 H18 0.89(5)
C19 C20 1.377(5)
C19 H19 0.95(4)
C20 C21 1.383(5)
C20 H20 0.92(4)
C21 H21 0.93(3)
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
N1 H1N O1 0.82(3) 1.97(3) 2.786(3) 170(3) 2_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 O1 -177.9(3)
C5 N1 C1 C2 1.3(4)
O1 C1 C2 C3 178.3(3)
N1 C1 C2 C3 -0.8(4)
C1 C2 C3 C4 0.3(4)
C2 C3 C4 C9 179.4(3)
C2 C3 C4 C5 -0.2(4)
C1 N1 C5 C6 179.8(3)
C1 N1 C5 C4 -1.2(4)
C9 C4 C5 N1 -179.0(2)
C3 C4 C5 N1 0.6(4)
C9 C4 C5 C6 0.0(4)
C3 C4 C5 C6 179.6(2)
N1 C5 C6 C7 179.5(2)
C4 C5 C6 C7 0.5(4)
C5 C6 C7 C8 -0.7(4)
C5 C6 C7 P1 -179.1(2)
C10 P1 C7 C6 162.4(2)
C16 P1 C7 C6 -91.8(2)
C10 P1 C7 C8 -15.9(3)
C16 P1 C7 C8 89.8(3)
C6 C7 C8 C9 0.3(4)
P1 C7 C8 C9 178.6(2)
C7 C8 C9 C4 0.2(5)
C5 C4 C9 C8 -0.4(4)
C3 C4 C9 C8 -180.0(3)
C16 P1 C10 C15 157.8(2)
C7 P1 C10 C15 -96.5(2)
C16 P1 C10 C11 -25.0(3)
C7 P1 C10 C11 80.7(3)
C15 C10 C11 C12 1.8(5)
P1 C10 C11 C12 -175.4(3)
C10 C11 C12 C13 -0.4(6)
C11 C12 C13 C14 -1.0(6)
C12 C13 C14 C15 1.0(6)
C13 C14 C15 C10 0.5(5)
C11 C10 C15 C14 -1.8(5)
P1 C10 C15 C14 175.6(3)
C10 P1 C16 C21 115.4(3)
C7 P1 C16 C21 10.2(3)
C10 P1 C16 C17 -69.1(3)
C7 P1 C16 C17 -174.2(2)
C21 C16 C17 C18 -0.4(5)
P1 C16 C17 C18 -176.3(3)
C16 C17 C18 C19 0.7(6)
C17 C18 C19 C20 -0.6(6)
C18 C19 C20 C21 0.3(6)
C17 C16 C21 C20 0.0(5)
P1 C16 C21 C20 175.5(2)
C19 C20 C21 C16 0.0(5)
