#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/56/7215665.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_7215665
loop_
_publ_author_name
'Puigjaner, Cristina'
'Vela, Sergi'
'Font-Bardia, Merce'
'Novoa, Juan J.'
_publ_section_title
;
 The Polymorphism of a Triarylphosphine oxide. A case of missing isomers.
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/c4ce00498a
_journal_year                    2014
_chemical_formula_moiety         'C18 H14 N O3 P'
_chemical_formula_sum            'C18 H14 N O3 P'
_chemical_formula_weight         323.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2012
_cell_angle_alpha                90
_cell_angle_beta                 119.16(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.075(6)
_cell_length_b                   11.026(6)
_cell_length_c                   16.317(8)
_cell_measurement_reflns_used    1298
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      31
_cell_measurement_theta_min      3
_cell_volume                     1582.9(16)
_computing_cell_refinement       'AUTOMAR (Claudio Klein, 2007)'
_computing_data_collection       'MARXDS (Claudio Klein, 2005)'
_computing_data_reduction        'MARSCALE (Claudio Klein, 2007)'
_computing_molecular_graphics    'ORTEP (Brueggermann and Smith, 1990)'
_computing_publication_material  'PLATON (Spek, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.958
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_device_type  'MAR345 with image plate detector'
_diffrn_measurement_method       'psi scan'
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.958
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14640
_diffrn_reflns_point_group_measured_fraction_full 0.958
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.476
_diffrn_reflns_theta_min         2.315
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       prism
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.0077(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5002
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0927
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0589P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1189
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3311
_reflns_number_total             5002
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ce00498a2.cif
_cod_data_source_block           anpm122a1
_cod_original_cell_volume        1582.9(15)
_cod_database_code               7215665
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2012-9
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
P1 P 0.83624(5) 0.77958(3) 0.81683(3) 0.04675(13) Uani 1 1 d . .
O1 O 0.73597(12) 0.85020(10) 0.84221(8) 0.0552(3) Uani 1 1 d . .
O2 O 0.87351(17) 1.04596(12) 0.78284(10) 0.0766(4) Uani 1 1 d . .
O3 O 0.64062(18) 1.09139(13) 0.68536(12) 0.0895(5) Uani 1 1 d . .
N1 N 0.75249(18) 1.02658(13) 0.71238(12) 0.0627(4) Uani 1 1 d . U
C1 C 0.79126(17) 0.80726(14) 0.69596(11) 0.0517(4) Uani 1 1 d . .
C2 C 0.74341(19) 0.92063(16) 0.65431(11) 0.0575(4) Uani 1 1 d . U
C3 C 0.6902(2) 0.9420(2) 0.56017(13) 0.0711(5) Uani 1 1 d . .
H3 H 0.6560 1.0185 0.5346 0.085 Uiso 1 1 calc R U
C4 C 0.6891(2) 0.8461(2) 0.50429(13) 0.0788(6) Uani 1 1 d . .
H4 H 0.6545 0.8585 0.4407 0.095 Uiso 1 1 calc R U
C5 C 0.7385(2) 0.7341(2) 0.54248(13) 0.0719(5) Uani 1 1 d . .
H5 H 0.7393 0.6710 0.5050 0.086 Uiso 1 1 calc R U
C6 C 0.78781(19) 0.71363(16) 0.63713(12) 0.0583(4) Uani 1 1 d . .
H6 H 0.8190 0.6362 0.6617 0.070 Uiso 1 1 calc R U
C7 C 0.80699(17) 0.61920(13) 0.81978(11) 0.0492(3) Uani 1 1 d . .
C8 C 0.65707(19) 0.57682(16) 0.77150(12) 0.0590(4) Uani 1 1 d . .
H8 H 0.5784 0.6314 0.7384 0.071 Uiso 1 1 calc R U
C9 C 0.6240(2) 0.45585(17) 0.77210(14) 0.0679(5) Uani 1 1 d . .
H9 H 0.5241 0.4285 0.7393 0.082 Uiso 1 1 calc R U
C10 C 0.7414(2) 0.37558(17) 0.82221(15) 0.0766(6) Uani 1 1 d . .
H10 H 0.7203 0.2936 0.8227 0.092 Uiso 1 1 calc R U
C11 C 0.8889(2) 0.41567(16) 0.87134(16) 0.0776(6) Uani 1 1 d . .
H11 H 0.9666 0.3607 0.9054 0.093 Uiso 1 1 calc R U
C12 C 0.9228(2) 0.53711(14) 0.87059(13) 0.0603(4) Uani 1 1 d . .
H12 H 1.0230 0.5637 0.9040 0.072 Uiso 1 1 calc R U
C13 C 1.03572(17) 0.81189(13) 0.89008(11) 0.0480(3) Uani 1 1 d . U
C14 C 1.0828(2) 0.86279(14) 0.97809(11) 0.0549(4) Uani 1 1 d . .
H14 H 1.0126 0.8752 0.9988 0.066 Uiso 1 1 calc R U
C15 C 1.2335(2) 0.89507(17) 1.03510(13) 0.0646(4) Uani 1 1 d . .
H15 H 1.2641 0.9296 1.0936 0.078 Uiso 1 1 calc R U
C16 C 1.3384(2) 0.87586(16) 1.00500(14) 0.0683(5) Uani 1 1 d . .
H16 H 1.4397 0.8968 1.0437 0.082 Uiso 1 1 calc R U
C17 C 1.2938(2) 0.82568(18) 0.91770(14) 0.0701(5) Uani 1 1 d . .
H17 H 1.3646 0.8132 0.8975 0.084 Uiso 1 1 calc R U
C18 C 1.14297(19) 0.79407(15) 0.86057(13) 0.0591(4) Uani 1 1 d . U
H18 H 1.1128 0.7605 0.8018 0.071 Uiso 1 1 calc R U
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 C7 111.44(7)
O1 P1 C13 113.66(8)
C7 P1 C13 108.72(7)
O1 P1 C1 111.71(7)
C7 P1 C1 103.68(7)
C13 P1 C1 107.06(8)
O2 N1 O3 124.10(18)
O2 N1 C2 117.62(14)
O3 N1 C2 118.23(16)
C2 C1 C6 116.16(16)
C2 C1 P1 121.56(13)
C6 C1 P1 121.96(13)
C3 C2 C1 123.47(18)
C3 C2 N1 116.64(17)
C1 C2 N1 119.87(15)
C2 C3 C4 118.35(19)
C2 C3 H3 120.8
C4 C3 H3 120.8
C5 C4 C3 120.24(18)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.54(19)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 121.19(18)
C5 C6 H6 119.4
C1 C6 H6 119.4
C12 C7 C8 118.76(15)
C12 C7 P1 123.82(13)
C8 C7 P1 117.34(12)
C9 C8 C7 121.19(17)
C9 C8 H8 119.4
C7 C8 H8 119.4
C8 C9 C10 119.01(18)
C8 C9 H9 120.5
C10 C9 H9 120.5
C11 C10 C9 120.68(18)
C11 C10 H10 119.7
C9 C10 H10 119.7
C10 C11 C12 120.54(18)
C10 C11 H11 119.7
C12 C11 H11 119.7
C11 C12 C7 119.80(17)
C11 C12 H12 120.1
C7 C12 H12 120.1
C14 C13 C18 118.76(15)
C14 C13 P1 118.20(12)
C18 C13 P1 122.95(13)
C15 C14 C13 120.44(17)
C15 C14 H14 119.8
C13 C14 H14 119.8
C16 C15 C14 119.99(18)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C17 120.42(18)
C15 C16 H16 119.8
C17 C16 H16 119.8
C16 C17 C18 119.54(18)
C16 C17 H17 120.2
C18 C17 H17 120.2
C17 C18 C13 120.85(16)
C17 C18 H18 119.6
C13 C18 H18 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 O1 1.4854(12)
P1 C7 1.7973(18)
P1 C13 1.804(2)
P1 C1 1.8214(19)
O2 N1 1.220(2)
O3 N1 1.221(2)
N1 C2 1.479(2)
C1 C2 1.392(2)
C1 C6 1.399(2)
C2 C3 1.378(2)
C3 C4 1.393(3)
C3 H3 0.9300
C4 C5 1.363(3)
C4 H4 0.9300
C5 C6 1.391(3)
C5 H5 0.9300
C6 H6 0.9300
C7 C12 1.388(2)
C7 C8 1.400(2)
C8 C9 1.376(3)
C8 H8 0.9300
C9 C10 1.381(3)
C9 H9 0.9300
C10 C11 1.373(3)
C10 H10 0.9300
C11 C12 1.383(2)
C11 H11 0.9300
C12 H12 0.9300
C13 C14 1.392(2)
C13 C18 1.395(2)
C14 C15 1.386(3)
C14 H14 0.9300
C15 C16 1.382(3)
C15 H15 0.9300
C16 C17 1.383(3)
C16 H16 0.9300
C17 C18 1.385(2)
C17 H17 0.9300
C18 H18 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 18410328
