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#$Date: 2025-08-20 16:06:16 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301830 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/07/13/4071307.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_4071307
loop_
_publ_author_name
'Nakabuchi, Takashi'
'Matano, Yoshihiro'
'Imahori, Hiroshi'
_publ_section_title
;
 Synthesis, Structures, and Coordinating Properties of
 Phosphole-Containing Hybrid Calixpyrroles
;
_journal_issue                   13
_journal_name_full               Organometallics
_journal_page_first              3142
_journal_paper_doi               10.1021/om800099h
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C37 H43 N2 O P S '
_chemical_formula_sum            'C37 H43 N2 O P S'
_chemical_formula_weight         594.77
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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                 109.3780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.962(4)
_cell_length_b                   15.735(4)
_cell_length_c                   15.131(5)
_cell_measurement_reflns_used    8760
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.0
_cell_volume                     3135.8(16)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure 3.8'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR97
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_sigmaI/netI    0.0224
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24261
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.02
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9636
_exptl_absorpt_correction_T_min  0.9124
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         6852
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.002
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0050P)²+3.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0755
_refine_ls_wR_factor_ref         0.0785
_reflns_number_gt                6258
_reflns_number_total             6852
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800099h-file001.cif
_cod_data_source_block           10O
_cod_original_cell_volume        3135.8(15)
_cod_database_code               4071307
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
S1 S 0.94529(3) 0.43660(2) 0.59415(3) 0.02087(9) Uani 1 1 d .
P1 P 0.87049(3) 0.36960(2) 0.66023(3) 0.01640(8) Uani 1 1 d .
O1 O 1.15706(8) 0.61905(6) 0.80717(7) 0.0194(2) Uani 1 1 d .
N1 N 0.92196(10) 0.57657(8) 0.77229(9) 0.0191(3) Uani 1 1 d .
H42 H 0.9530 0.5477 0.7398 0.022 Uiso 1 1 d .
N2 N 1.15650(9) 0.40479(8) 0.80759(9) 0.0184(3) Uani 1 1 d .
H43 H 1.1165 0.4268 0.7547 0.022 Uiso 1 1 d .
C1 C 0.77516(11) 0.42761(9) 0.69318(11) 0.0180(3) Uani 1 1 d .
C2 C 0.82159(11) 0.45010(9) 0.79690(11) 0.0177(3) Uani 1 1 d .
C3 C 0.76345(12) 0.42625(10) 0.86436(11) 0.0230(3) Uani 1 1 d .
H1 H 0.7128 0.4704 0.8640 0.028 Uiso 1 1 calc R
H2 H 0.7282 0.3711 0.8466 0.028 Uiso 1 1 calc R
C4 C 0.84664(13) 0.42059(11) 0.96144(12) 0.0271(4) Uani 1 1 d .
H3 H 0.8293 0.3766 1.0005 0.033 Uiso 1 1 calc R
H4 H 0.8546 0.4758 0.9944 0.033 Uiso 1 1 calc R
C5 C 0.94517(13) 0.39662(12) 0.94202(12) 0.0303(4) Uani 1 1 d .
H5 H 0.9983 0.4402 0.9675 0.036 Uiso 1 1 calc R
H6 H 0.9713 0.3410 0.9704 0.036 Uiso 1 1 calc R
C6 C 0.91430(11) 0.39259(9) 0.83711(11) 0.0181(3) Uani 1 1 d .
C7 C 0.94625(11) 0.34446(9) 0.77935(11) 0.0169(3) Uani 1 1 d .
C8 C 0.68406(12) 0.45032(10) 0.63408(12) 0.0230(3) Uani 1 1 d .
C9 C 0.64608(14) 0.42726(11) 0.53162(12) 0.0323(4) Uani 1 1 d .
H7 H 0.7005 0.3992 0.5151 0.039 Uiso 1 1 calc R
H8 H 0.6250 0.4789 0.4940 0.039 Uiso 1 1 calc R
H9 H 0.5880 0.3886 0.5192 0.039 Uiso 1 1 calc R
C10 C 0.60926(13) 0.50160(11) 0.66482(13) 0.0304(4) Uani 1 1 d .
H10 H 0.5571 0.4638 0.6730 0.037 Uiso 1 1 calc R
H11 H 0.5772 0.5444 0.6171 0.037 Uiso 1 1 calc R
H12 H 0.6450 0.5300 0.7243 0.037 Uiso 1 1 calc R
C11 C 0.85224(11) 0.54312(9) 0.80926(11) 0.0186(3) Uani 1 1 d .
C12 C 0.82209(12) 0.60775(10) 0.85446(11) 0.0231(3) Uani 1 1 d .
H13 H 0.7744 0.6036 0.8868 0.028 Uiso 1 1 calc R
C13 C 0.87494(13) 0.68231(10) 0.84432(12) 0.0250(3) Uani 1 1 d .
H14 H 0.8687 0.7369 0.8686 0.030 Uiso 1 1 calc R
C14 C 0.93634(12) 0.66155(9) 0.79349(11) 0.0197(3) Uani 1 1 d .
C15 C 1.01009(12) 0.71523(9) 0.76300(11) 0.0206(3) Uani 1 1 d .
C16 C 0.95194(14) 0.77070(11) 0.67823(13) 0.0304(4) Uani 1 1 d .
H15 H 0.9999 0.8076 0.6616 0.037 Uiso 1 1 calc R
H16 H 0.9020 0.8057 0.6943 0.037 Uiso 1 1 calc R
H17 H 0.9170 0.7341 0.6249 0.037 Uiso 1 1 calc R
C17 C 1.06972(13) 0.77401(10) 0.84380(12) 0.0268(4) Uani 1 1 d .
H18 H 1.1046 0.7397 0.8992 0.032 Uiso 1 1 calc R
H19 H 1.0227 0.8133 0.8585 0.032 Uiso 1 1 calc R
H20 H 1.1198 0.8064 0.8251 0.032 Uiso 1 1 calc R
C18 C 1.08213(12) 0.65869(9) 0.73529(11) 0.0194(3) Uani 1 1 d .
C19 C 1.08892(13) 0.63428(10) 0.65263(12) 0.0240(3) Uani 1 1 d .
H21 H 1.0457 0.6515 0.5924 0.029 Uiso 1 1 calc R
C20 C 1.17321(13) 0.57748(10) 0.67203(12) 0.0253(3) Uani 1 1 d .
H22 H 1.1972 0.5504 0.6273 0.030 Uiso 1 1 calc R
C21 C 1.21234(12) 0.56970(9) 0.76615(11) 0.0205(3) Uani 1 1 d .
C22 C 1.29548(12) 0.51580(10) 0.83089(12) 0.0220(3) Uani 1 1 d .
C23 C 1.36854(14) 0.48911(11) 0.77864(14) 0.0323(4) Uani 1 1 d .
H23 H 1.3321 0.4536 0.7248 0.039 Uiso 1 1 calc R
H24 H 1.4253 0.4569 0.8211 0.039 Uiso 1 1 calc R
H25 H 1.3946 0.5399 0.7568 0.039 Uiso 1 1 calc R
C24 C 1.35542(13) 0.56639(10) 0.91885(13) 0.0282(4) Uani 1 1 d .
H26 H 1.3866 0.6162 0.9005 0.034 Uiso 1 1 calc R
H27 H 1.4086 0.5302 0.9604 0.034 Uiso 1 1 calc R
H28 H 1.3093 0.5850 0.9517 0.034 Uiso 1 1 calc R
C25 C 1.24977(11) 0.43737(9) 0.86019(11) 0.0192(3) Uani 1 1 d .
C26 C 1.28824(12) 0.38452(10) 0.93558(12) 0.0247(3) Uani 1 1 d .
H29 H 1.3519 0.3906 0.9840 0.030 Uiso 1 1 calc R
C27 C 1.21580(12) 0.31874(10) 0.92856(11) 0.0227(3) Uani 1 1 d .
H30 H 1.2228 0.2731 0.9714 0.027 Uiso 1 1 calc R
C28 C 1.13466(11) 0.33292(9) 0.84946(11) 0.0178(3) Uani 1 1 d .
C29 C 1.03751(11) 0.28317(9) 0.80627(11) 0.0184(3) Uani 1 1 d .
C30 C 1.02615(13) 0.21611(10) 0.87651(12) 0.0252(3) Uani 1 1 d .
H31 H 1.0759 0.1706 0.8826 0.030 Uiso 1 1 calc R
H32 H 0.9575 0.1922 0.8538 0.030 Uiso 1 1 calc R
H33 H 1.0379 0.2429 0.9377 0.030 Uiso 1 1 calc R
C31 C 1.04353(12) 0.23427(10) 0.71970(12) 0.0235(3) Uani 1 1 d .
H34 H 1.0461 0.2749 0.6714 0.028 Uiso 1 1 calc R
H35 H 0.9835 0.1980 0.6950 0.028 Uiso 1 1 calc R
H36 H 1.1048 0.1990 0.7378 0.028 Uiso 1 1 calc R
C32 C 0.81345(11) 0.27377(9) 0.59795(11) 0.0187(3) Uani 1 1 d .
C33 C 0.75304(12) 0.22267(10) 0.63315(12) 0.0241(3) Uani 1 1 d .
H37 H 0.7430 0.2370 0.6904 0.029 Uiso 1 1 calc R
C34 C 0.70758(13) 0.15057(11) 0.58375(14) 0.0305(4) Uani 1 1 d .
H38 H 0.6650 0.1164 0.6068 0.037 Uiso 1 1 calc R
C35 C 0.72365(14) 0.12811(11) 0.50182(13) 0.0322(4) Uani 1 1 d .
H39 H 0.6931 0.0782 0.4692 0.039 Uiso 1 1 calc R
C36 C 0.78433(15) 0.17821(11) 0.46696(13) 0.0335(4) Uani 1 1 d .
H40 H 0.7957 0.1627 0.4106 0.040 Uiso 1 1 calc R
C37 C 0.82865(13) 0.25131(10) 0.51484(12) 0.0267(4) Uani 1 1 d .
H41 H 0.8696 0.2861 0.4905 0.032 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'
S S 0.1246 0.1234 '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
C7 P1 C1 94.36(7)
C7 P1 C32 110.30(7)
C1 P1 C32 108.96(7)
C7 P1 S1 112.94(5)
C1 P1 S1 115.47(5)
C32 P1 S1 113.29(6)
C21 O1 C18 106.88(12)
C14 N1 C11 110.19(12)
C28 N2 C25 110.49(12)
C8 C1 C2 127.59(14)
C8 C1 P1 124.88(12)
C2 C1 P1 107.39(10)
C11 C2 C1 110.85(12)
C11 C2 C6 110.75(12)
C1 C2 C6 106.62(12)
C11 C2 C3 109.91(12)
C1 C2 C3 119.03(13)
C6 C2 C3 98.86(12)
C4 C3 C2 104.37(13)
C3 C4 C5 105.62(13)
C6 C5 C4 104.47(13)
C7 C6 C5 132.25(14)
C7 C6 C2 119.72(14)
C5 C6 C2 107.67(13)
C6 C7 C29 127.33(14)
C6 C7 P1 108.41(11)
C29 C7 P1 124.06(11)
C1 C8 C9 123.73(15)
C1 C8 C10 122.55(15)
C9 C8 C10 113.72(14)
C12 C11 N1 107.16(13)
C12 C11 C2 131.10(14)
N1 C11 C2 121.74(13)
C11 C12 C13 107.64(14)
C14 C13 C12 107.96(14)
C13 C14 N1 107.06(14)
C13 C14 C15 130.79(14)
N1 C14 C15 122.15(14)
C18 C15 C14 109.86(12)
C18 C15 C17 109.98(13)
C14 C15 C17 109.62(13)
C18 C15 C16 108.63(14)
C14 C15 C16 110.19(13)
C17 C15 C16 108.52(13)
C19 C18 O1 109.59(14)
C19 C18 C15 133.67(15)
O1 C18 C15 116.70(13)
C18 C19 C20 107.20(15)
C21 C20 C19 106.91(14)
C20 C21 O1 109.41(14)
C20 C21 C22 133.71(15)
O1 C21 C22 116.72(13)
C21 C22 C25 109.80(13)
C21 C22 C24 110.59(13)
C25 C22 C24 109.15(13)
C21 C22 C23 108.53(14)
C25 C22 C23 109.96(13)
C24 C22 C23 108.79(14)
C26 C25 N2 106.80(13)
C26 C25 C22 130.46(14)
N2 C25 C22 122.70(14)
C25 C26 C27 107.84(14)
C28 C27 C26 107.94(14)
C27 C28 N2 106.92(13)
C27 C28 C29 131.11(14)
N2 C28 C29 121.93(13)
C28 C29 C7 109.53(12)
C28 C29 C30 109.79(13)
C7 C29 C30 110.19(12)
C28 C29 C31 109.29(13)
C7 C29 C31 111.12(13)
C30 C29 C31 106.88(13)
C37 C32 C33 119.56(14)
C37 C32 P1 120.58(12)
C33 C32 P1 119.86(12)
C34 C33 C32 119.45(16)
C35 C34 C33 120.77(16)
C34 C35 C36 120.02(16)
C35 C36 C37 119.71(17)
C32 C37 C36 120.48(16)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 P1 1.9735(6)
P1 C7 1.8053(16)
P1 C1 1.8147(15)
P1 C32 1.8161(16)
O1 C21 1.3791(18)
O1 C18 1.3825(18)
N1 C14 1.3741(19)
N1 C11 1.3781(19)
N2 C28 1.3788(18)
N2 C25 1.380(2)
C1 C8 1.338(2)
C1 C2 1.528(2)
C2 C11 1.519(2)
C2 C6 1.530(2)
C2 C3 1.547(2)
C3 C4 1.543(2)
C4 C5 1.546(2)
C5 C6 1.502(2)
C6 C7 1.340(2)
C7 C29 1.541(2)
C8 C9 1.507(2)
C8 C10 1.510(2)
C11 C12 1.368(2)
C12 C13 1.421(2)
C13 C14 1.368(2)
C14 C15 1.517(2)
C15 C18 1.503(2)
C15 C17 1.539(2)
C15 C16 1.541(2)
C18 C19 1.341(2)
C19 C20 1.428(2)
C20 C21 1.351(2)
C21 C22 1.507(2)
C22 C25 1.521(2)
C22 C24 1.538(2)
C22 C23 1.542(2)
C25 C26 1.369(2)
C26 C27 1.426(2)
C27 C28 1.366(2)
C28 C29 1.514(2)
C29 C30 1.543(2)
C29 C31 1.545(2)
C32 C37 1.389(2)
C32 C33 1.393(2)
C33 C34 1.391(2)
C34 C35 1.377(3)
C35 C36 1.384(3)
C36 C37 1.390(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139102880
