#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/46/4504666.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_4504666
loop_
_publ_author_name
'Chandrasekhar, Vadapalli'
'Azhakar, Ramachandran'
'Bickley, Jamie F.'
'Steiner, Alexander'
_publ_section_title
;
 Influence of O−H···OP Hydrogen Bonding on the
 Supramolecular Architectures of Phosphorus-Based Hydrazones: 
 Alternate Right- and Left-Handed Fused Helical Chains Based on
 O−H···OP Hydrogen Bonds in the Crystal
 Structure of C6H5P(O)[N(CH3)NCHC6H4-p-OH]2
;
_journal_issue                   4
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              910
_journal_paper_doi               10.1021/cg050426v
_journal_volume                  6
_journal_year                    2006
_chemical_formula_sum            'C22 H23 N4 O3 P'
_chemical_formula_weight         422.41
_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           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 102.75(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.361(5)
_cell_length_b                   13.967(6)
_cell_length_c                   12.022(5)
_cell_measurement_temperature    100(2)
_cell_volume                     2188.1(17)
_computing_cell_refinement       'Bruker SMART V5.628'
_computing_data_collection       'Bruker SMART V5.628'
_computing_data_reduction        'Bruker SAINT+ V6.45'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SAINT+ V6.45'
_diffrn_ambient_temperature      100(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  0.0507
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14454
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_type   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             888
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         5406
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0706
_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)+(0.0829P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1516
_refine_ls_wR_factor_ref         0.1791
_reflns_number_gt                2968
_reflns_number_total             5406
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg050426vsi20060125_125302.cif
_cod_data_source_block           compound2
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2188.3(15)
_cod_original_sg_symbol_H-M      'P2(1)/c  '
_cod_database_code               4504666
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
P1 P 0.22012(5) 0.00006(5) 0.69875(5) 0.0431(2) Uani 1 1 d .
O1 O 0.18905(15) -0.05548(14) 0.79056(14) 0.0531(5) Uani 1 1 d .
O2 O 0.72516(19) 0.23528(17) 1.1631(2) 0.0865(8) Uani 1 1 d .
H2 H 0.7501 0.1816 1.1640 0.130 Uiso 1 1 calc R
O3 O 0.1346(2) -0.0737(2) -0.01390(17) 0.0887(9) Uani 1 1 d .
H3 H 0.1541 -0.0534 -0.0695 0.133 Uiso 1 1 calc R
N1 N 0.34545(17) 0.02028(16) 0.71741(18) 0.0471(6) Uani 1 1 d .
N2 N 0.37428(17) 0.08809(16) 0.80291(18) 0.0458(6) Uani 1 1 d .
N3 N 0.19104(18) -0.06278(17) 0.57964(17) 0.0508(6) Uani 1 1 d .
N4 N 0.21911(17) -0.02005(16) 0.48629(17) 0.0473(6) Uani 1 1 d .
C1 C 0.1599(2) 0.1140(2) 0.6821(2) 0.0488(7) Uani 1 1 d .
C2 C 0.1037(3) 0.1431(3) 0.7594(3) 0.0763(10) Uani 1 1 d .
H2A H 0.0987 0.1030 0.8196 0.092 Uiso 1 1 calc R
C3 C 0.0551(3) 0.2304(3) 0.7490(4) 0.0992(14) Uani 1 1 d .
H3A H 0.0190 0.2493 0.8032 0.119 Uiso 1 1 calc R
C4 C 0.0593(3) 0.2894(3) 0.6603(5) 0.0899(13) Uani 1 1 d .
H4 H 0.0260 0.3483 0.6533 0.108 Uiso 1 1 calc R
C5 C 0.1132(3) 0.2610(3) 0.5812(3) 0.0821(12) Uani 1 1 d .
H5 H 0.1154 0.3005 0.5194 0.098 Uiso 1 1 calc R
C6 C 0.1639(3) 0.1748(2) 0.5927(3) 0.0647(9) Uani 1 1 d .
H6 H 0.2015 0.1571 0.5394 0.078 Uiso 1 1 calc R
C7 C 0.4184(2) -0.0510(2) 0.6940(3) 0.0550(8) Uani 1 1 d .
H7A H 0.4734 -0.0193 0.6694 0.083 Uiso 1 1 calc R
H7B H 0.3840 -0.0936 0.6352 0.083 Uiso 1 1 calc R
H7C H 0.4455 -0.0869 0.7621 0.083 Uiso 1 1 calc R
C8 C 0.4676(2) 0.09450(19) 0.8569(2) 0.0460(7) Uani 1 1 d .
H8 H 0.5163 0.0524 0.8404 0.055 Uiso 1 1 calc R
C9 C 0.4983(2) 0.16828(19) 0.9450(2) 0.0440(6) Uani 1 1 d .
C10 C 0.5967(2) 0.1670(2) 1.0104(2) 0.0521(7) Uani 1 1 d .
H10 H 0.6424 0.1201 0.9979 0.063 Uiso 1 1 calc R
C11 C 0.6287(2) 0.2351(2) 1.0953(3) 0.0543(7) Uani 1 1 d .
C12 C 0.5619(3) 0.3047(2) 1.1123(3) 0.0664(9) Uani 1 1 d .
H12 H 0.5830 0.3513 1.1678 0.080 Uiso 1 1 calc R
C13 C 0.4634(3) 0.3059(2) 1.0471(3) 0.0749(10) Uani 1 1 d .
H13 H 0.4181 0.3532 1.0595 0.090 Uiso 1 1 calc R
C14 C 0.4306(2) 0.2385(2) 0.9641(3) 0.0603(8) Uani 1 1 d .
H14 H 0.3636 0.2398 0.9211 0.072 Uiso 1 1 calc R
C15 C 0.1272(3) -0.1479(3) 0.5670(3) 0.0976(15) Uani 1 1 d .
H15A H 0.0611 -0.1336 0.5197 0.146 Uiso 1 1 calc R
H15B H 0.1191 -0.1686 0.6406 0.146 Uiso 1 1 calc R
H15C H 0.1591 -0.1979 0.5323 0.146 Uiso 1 1 calc R
C16 C 0.1866(2) -0.0575(2) 0.3891(2) 0.0498(7) Uani 1 1 d .
H16 H 0.1442 -0.1109 0.3830 0.060 Uiso 1 1 calc R
C17 C 0.2134(2) -0.0196(2) 0.2862(2) 0.0443(7) Uani 1 1 d .
C18 C 0.1653(2) -0.0598(2) 0.1833(2) 0.0548(8) Uani 1 1 d .
H18 H 0.1171 -0.1081 0.1822 0.066 Uiso 1 1 calc R
C19 C 0.1875(3) -0.0294(2) 0.0820(2) 0.0550(8) Uani 1 1 d .
C20 C 0.2591(2) 0.0412(2) 0.0831(2) 0.0532(8) Uani 1 1 d .
H20 H 0.2753 0.0613 0.0154 0.064 Uiso 1 1 calc R
C21 C 0.3069(2) 0.0819(2) 0.1857(2) 0.0535(8) Uani 1 1 d .
H21 H 0.3548 0.1303 0.1864 0.064 Uiso 1 1 calc R
C22 C 0.2851(2) 0.0522(2) 0.2869(2) 0.0505(7) Uani 1 1 d .
H22 H 0.3183 0.0801 0.3553 0.061 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'
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
O1 P1 N3 108.47(12)
O1 P1 N1 115.31(12)
N3 P1 N1 104.15(11)
O1 P1 C1 111.02(12)
N3 P1 C1 111.40(13)
N1 P1 C1 106.32(13)
N2 N1 C7 121.3(2)
N2 N1 P1 108.80(16)
C7 N1 P1 123.49(19)
C8 N2 N1 120.3(2)
N4 N3 C15 121.5(2)
N4 N3 P1 114.65(18)
C15 N3 P1 123.13(19)
C16 N4 N3 117.9(2)
C2 C1 C6 117.7(3)
C2 C1 P1 119.3(2)
C6 C1 P1 123.0(2)
C3 C2 C1 121.2(4)
C4 C3 C2 120.5(4)
C3 C4 C5 119.3(4)
C4 C5 C6 120.4(4)
C5 C6 C1 120.9(3)
N2 C8 C9 120.1(3)
C10 C9 C14 119.4(3)
C10 C9 C8 118.9(2)
C14 C9 C8 121.8(3)
C9 C10 C11 120.7(3)
O2 C11 C12 118.2(3)
O2 C11 C10 122.4(3)
C12 C11 C10 119.4(3)
C11 C12 C13 119.9(3)
C14 C13 C12 121.2(3)
C13 C14 C9 119.4(3)
N4 C16 C17 122.2(3)
C18 C17 C22 119.0(2)
C18 C17 C16 117.2(3)
C22 C17 C16 123.8(2)
C17 C18 C19 121.1(3)
O3 C19 C20 124.4(3)
O3 C19 C18 115.8(3)
C20 C19 C18 119.8(3)
C19 C20 C21 119.2(3)
C22 C21 C20 121.3(3)
C21 C22 C17 119.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4814(18)
P1 N3 1.651(2)
P1 N1 1.664(2)
P1 C1 1.775(3)
O2 C11 1.364(4)
O3 C19 1.361(3)
N1 N2 1.388(3)
N1 C7 1.463(3)
N2 C8 1.275(3)
N3 N4 1.394(3)
N3 C15 1.452(4)
N4 C16 1.267(3)
C1 C2 1.378(4)
C1 C6 1.380(4)
C2 C3 1.375(5)
C3 C4 1.358(5)
C4 C5 1.372(5)
C5 C6 1.375(5)
C8 C9 1.470(4)
C9 C10 1.376(4)
C9 C14 1.388(4)
C10 C11 1.392(4)
C11 C12 1.365(4)
C12 C13 1.376(5)
C13 C14 1.371(4)
C16 C17 1.461(3)
C17 C18 1.381(4)
C17 C22 1.385(4)
C18 C19 1.382(4)
C19 C20 1.372(4)
C20 C21 1.381(4)
C21 C22 1.376(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30661469
