#------------------------------------------------------------------------------
#$Date: 2019-12-20 23:46:17 +0200 (Fri, 20 Dec 2019) $
#$Revision: 245439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/72/4517231.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_4517231
loop_
_publ_author_name
'Alice Heskia'
'Thierry Maris'
'James D. Wuest'
_publ_section_title
;
 Foiling Normal Patterns of Crystallization by Design. Polymorphism of
 Phosphangulene Chalcogenides
;
_journal_name_full               'Cryst. Growth & Design'
_journal_page_first              5390
_journal_page_last               5406
_journal_paper_doi               10.1021/acs.cgd.9b00907
_journal_volume                  19
_journal_year                    2019
_chemical_formula_moiety         'C18 H9 O3.5 P'
_chemical_formula_sum            'C18 H9 O3.5 P'
_chemical_formula_weight         312.28
_chemical_name_systematic
'phosphangulene oxide : phosphangulene 0.50:0.50'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_contact_author_name
;
;
_audit_creation_date             2018-11-13
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.0382(8)
_cell_length_b                   7.4286(5)
_cell_length_c                   29.694(2)
_cell_measurement_reflns_used    9810
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.803
_cell_measurement_theta_min      2.590
_cell_volume                     2655.4(3)
_computing_cell_refinement
;       
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.'
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data. 
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            26465
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.025
_diffrn_reflns_theta_min         2.589
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    1.287
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5061
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;   
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.1518 before and 0.1003 after correction. 
The Ratio of minimum to maximum transmission is 0.6741. 
The λ/2 correction factor is Not present.'
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_description       Block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       0.0044(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2505
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0624
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0561P)²+6.3612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.1636
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2388
_reflns_number_total             2505
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            phango_phang_jw21275.cif
_cod_data_source_block           jw21275
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C18 H9 O3.50 P'
_cod_database_code               4517231
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 '-x, y+1/2, -z+1/2'
4 'x+1/2, -y+1/2, -z'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 'x, -y-1/2, z-1/2'
8 '-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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1A P 0.51787(7) 0.51030(13) 0.62194(3) 0.0336(3) Uani 1 1 d . . . . .
O1A O 0.38864(19) 0.7520(3) 0.56073(7) 0.0368(6) Uani 1 1 d . . . . .
O2A O 0.7486(2) 0.4855(3) 0.58424(7) 0.0363(6) Uani 1 1 d . . . . .
O3A O 0.53542(19) 0.6990(3) 0.71101(7) 0.0358(6) Uani 1 1 d . . . . .
O4A O 0.4644(4) 0.3448(6) 0.62459(14) 0.0302(16) Uani 0.504(9) 1 d . . . . .
C1A C 0.5625(3) 0.5926(4) 0.56913(11) 0.0320(7) Uani 1 1 d . . . . .
C2A C 0.4918(3) 0.6986(4) 0.54316(11) 0.0324(7) Uani 1 1 d . . . . .
C3A C 0.5222(3) 0.7515(5) 0.50063(12) 0.0348(7) Uani 1 1 d . . . . .
H3A H 0.473131 0.819653 0.482283 0.042 Uiso 1 1 calc R . . . .
C4A C 0.6273(3) 0.7024(5) 0.48508(12) 0.0364(8) Uani 1 1 d . . . . .
H4A H 0.647274 0.731227 0.454983 0.044 Uiso 1 1 calc R . . . .
C5A C 0.7037(3) 0.6128(5) 0.51202(11) 0.0354(7) Uani 1 1 d . . . . .
H5A H 0.776312 0.586927 0.501299 0.042 Uiso 1 1 calc R . . . .
C6A C 0.6712(3) 0.5622(4) 0.55490(11) 0.0317(7) Uani 1 1 d . . . . .
C7A C 0.6425(3) 0.5624(4) 0.65083(11) 0.0302(7) Uani 1 1 d . . . . .
C8A C 0.7443(3) 0.5408(4) 0.62912(11) 0.0317(7) Uani 1 1 d . . . . .
C9A C 0.8423(3) 0.5784(4) 0.65169(11) 0.0333(7) Uani 1 1 d . . . . .
H9A H 0.912264 0.558582 0.637708 0.040 Uiso 1 1 calc R . . . .
C10A C 0.8359(3) 0.6457(5) 0.69523(12) 0.0359(8) Uani 1 1 d . . . . .
H10A H 0.902739 0.664807 0.711567 0.043 Uiso 1 1 calc R . . . .
C11A C 0.7351(3) 0.6861(5) 0.71576(11) 0.0354(7) Uani 1 1 d . . . . .
H11A H 0.732745 0.738913 0.744886 0.042 Uiso 1 1 calc R . . . .
C12A C 0.6382(3) 0.6470(4) 0.69247(11) 0.0311(7) Uani 1 1 d . . . . .
C13A C 0.4457(3) 0.7085(4) 0.63814(11) 0.0309(7) Uani 1 1 d . . . . .
C14A C 0.3861(3) 0.8035(5) 0.60617(11) 0.0320(7) Uani 1 1 d . . . . .
C15A C 0.3241(3) 0.9518(5) 0.61877(11) 0.0343(7) Uani 1 1 d . . . . .
H15A H 0.279860 1.014482 0.597437 0.041 Uiso 1 1 calc R . . . .
C16A C 0.3283(3) 1.0067(5) 0.66353(12) 0.0374(8) Uani 1 1 d . . . . .
H16A H 0.282942 1.104286 0.672976 0.045 Uiso 1 1 calc R . . . .
C17A C 0.3972(3) 0.9229(5) 0.69495(11) 0.0357(8) Uani 1 1 d . . . . .
H17A H 0.401687 0.965864 0.725033 0.043 Uiso 1 1 calc R . . . .
C18A C 0.4584(3) 0.7769(5) 0.68132(11) 0.0319(7) Uani 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 0.0137 0.0067 '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'
O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2543 0.3332 '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
O4A P1A C1A 119.8(2) . .
O4A P1A C7A 123.9(2) . .
O4A P1A C13A 119.4(2) . .
C1A P1A C7A 95.54(15) . .
C1A P1A C13A 95.88(15) . .
C7A P1A C13A 95.86(15) . .
C14A O1A C2A 117.0(2) . .
C8A O2A C6A 116.8(2) . .
C18A O3A C12A 116.6(2) . .
C2A C1A P1A 120.1(3) . .
C6A C1A P1A 119.9(3) . .
C6A C1A C2A 119.8(3) . .
C1A C2A O1A 119.6(3) . .
C3A C2A O1A 119.8(3) . .
C3A C2A C1A 120.5(3) . .
C2A C3A H3A 120.9 . .
C2A C3A C4A 118.1(3) . .
C4A C3A H3A 120.9 . .
C3A C4A H4A 118.8 . .
C5A C4A C3A 122.4(3) . .
C5A C4A H4A 118.8 . .
C4A C5A H5A 120.9 . .
C6A C5A C4A 118.2(3) . .
C6A C5A H5A 120.9 . .
C1A C6A O2A 120.2(3) . .
C5A C6A O2A 119.7(3) . .
C5A C6A C1A 120.1(3) . .
C8A C7A P1A 119.7(2) . .
C12A C7A P1A 119.9(2) . .
C12A C7A C8A 119.9(3) . .
C7A C8A O2A 120.5(3) . .
C9A C8A O2A 119.3(3) . .
C9A C8A C7A 120.1(3) . .
C8A C9A H9A 120.8 . .
C8A C9A C10A 118.4(3) . .
C10A C9A H9A 120.8 . .
C9A C10A H10A 118.8 . .
C9A C10A C11A 122.3(3) . .
C11A C10A H10A 118.8 . .
C10A C11A H11A 121.0 . .
C12A C11A C10A 118.0(3) . .
C12A C11A H11A 121.0 . .
C7A C12A O3A 120.4(3) . .
C11A C12A O3A 119.1(3) . .
C11A C12A C7A 120.5(3) . .
C14A C13A P1A 119.4(2) . .
C14A C13A C18A 120.3(3) . .
C18A C13A P1A 120.0(2) . .
C13A C14A O1A 120.6(3) . .
C15A C14A O1A 119.3(3) . .
C15A C14A C13A 120.1(3) . .
C14A C15A H15A 120.9 . .
C14A C15A C16A 118.2(3) . .
C16A C15A H15A 120.9 . .
C15A C16A H16A 119.0 . .
C15A C16A C17A 122.0(3) . .
C17A C16A H16A 119.0 . .
C16A C17A H17A 120.8 . .
C18A C17A C16A 118.3(3) . .
C18A C17A H17A 120.8 . .
C13A C18A O3A 120.1(3) . .
C17A C18A O3A 119.7(3) . .
C17A C18A C13A 120.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
P1A O4A 1.390(4) .
P1A C1A 1.767(3) .
P1A C7A 1.772(3) .
P1A C13A 1.776(3) .
O1A C2A 1.404(4) .
O1A C14A 1.403(4) .
O2A C6A 1.397(4) .
O2A C8A 1.395(4) .
O3A C12A 1.408(4) .
O3A C18A 1.404(4) .
C1A C2A 1.393(5) .
C1A C6A 1.393(5) .
C2A C3A 1.372(5) .
C3A H3A 0.9500 .
C3A C4A 1.395(5) .
C4A H4A 0.9500 .
C4A C5A 1.389(5) .
C5A H5A 0.9500 .
C5A C6A 1.384(5) .
C7A C8A 1.394(5) .
C7A C12A 1.388(5) .
C8A C9A 1.385(5) .
C9A H9A 0.9500 .
C9A C10A 1.388(5) .
C10A H10A 0.9500 .
C10A C11A 1.391(5) .
C11A H11A 0.9500 .
C11A C12A 1.388(5) .
C13A C14A 1.384(5) .
C13A C18A 1.388(5) .
C14A C15A 1.382(5) .
C15A H15A 0.9500 .
C15A C16A 1.391(5) .
C16A H16A 0.9500 .
C16A C17A 1.395(5) .
C17A H17A 0.9500 .
C17A C18A 1.372(5) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
P1A C1A C2A O1A 5.2(4) . . . .
P1A C1A C2A C3A -174.9(3) . . . .
P1A C1A C6A O2A -7.4(4) . . . .
P1A C1A C6A C5A 174.4(3) . . . .
P1A C7A C8A O2A 2.7(4) . . . .
P1A C7A C8A C9A -178.9(3) . . . .
P1A C7A C12A O3A -2.9(4) . . . .
P1A C7A C12A C11A 179.0(3) . . . .
P1A C13A C14A O1A -4.5(4) . . . .
P1A C13A C14A C15A 176.1(3) . . . .
P1A C13A C18A O3A 5.6(4) . . . .
P1A C13A C18A C17A -175.7(3) . . . .
O1A C2A C3A C4A 177.3(3) . . . .
O1A C14A C15A C16A -176.1(3) . . . .
O2A C8A C9A C10A 175.4(3) . . . .
O4A P1A C1A C2A 90.0(3) . . . .
O4A P1A C1A C6A -94.6(3) . . . .
O4A P1A C7A C8A 94.3(3) . . . .
O4A P1A C7A C12A -94.3(3) . . . .
O4A P1A C13A C14A -90.7(3) . . . .
O4A P1A C13A C18A 95.8(3) . . . .
C1A P1A C7A C8A -37.5(3) . . . .
C1A P1A C7A C12A 133.8(3) . . . .
C1A P1A C13A C14A 38.5(3) . . . .
C1A P1A C13A C18A -135.0(3) . . . .
C1A C2A C3A C4A -2.6(5) . . . .
C2A O1A C14A C13A -41.0(4) . . . .
C2A O1A C14A C15A 138.4(3) . . . .
C2A C1A C6A O2A 168.0(3) . . . .
C2A C1A C6A C5A -10.2(5) . . . .
C2A C3A C4A C5A -4.2(5) . . . .
C3A C4A C5A C6A 3.7(5) . . . .
C4A C5A C6A O2A -174.6(3) . . . .
C4A C5A C6A C1A 3.5(5) . . . .
C6A O2A C8A C7A 41.7(4) . . . .
C6A O2A C8A C9A -136.7(3) . . . .
C6A C1A C2A O1A -170.2(3) . . . .
C6A C1A C2A C3A 9.7(5) . . . .
C7A P1A C1A C2A -135.4(3) . . . .
C7A P1A C1A C6A 39.9(3) . . . .
C7A P1A C13A C14A 134.7(3) . . . .
C7A P1A C13A C18A -38.8(3) . . . .
C7A C8A C9A C10A -3.1(5) . . . .
C8A O2A C6A C1A -39.1(4) . . . .
C8A O2A C6A C5A 139.1(3) . . . .
C8A C7A C12A O3A 168.4(3) . . . .
C8A C7A C12A C11A -9.7(5) . . . .
C8A C9A C10A C11A -3.8(5) . . . .
C9A C10A C11A C12A 3.9(5) . . . .
C10A C11A C12A O3A -175.2(3) . . . .
C10A C11A C12A C7A 2.9(5) . . . .
C12A O3A C18A C13A 40.3(4) . . . .
C12A O3A C18A C17A -138.5(3) . . . .
C12A C7A C8A O2A -168.7(3) . . . .
C12A C7A C8A C9A 9.8(5) . . . .
C13A P1A C1A C2A -39.0(3) . . . .
C13A P1A C1A C6A 136.4(3) . . . .
C13A P1A C7A C8A -134.0(3) . . . .
C13A P1A C7A C12A 37.3(3) . . . .
C13A C14A C15A C16A 3.2(5) . . . .
C14A O1A C2A C1A 40.5(4) . . . .
C14A O1A C2A C3A -139.4(3) . . . .
C14A C13A C18A O3A -167.9(3) . . . .
C14A C13A C18A C17A 10.9(5) . . . .
C14A C15A C16A C17A 3.5(5) . . . .
C15A C16A C17A C18A -3.0(5) . . . .
C16A C17A C18A O3A 174.6(3) . . . .
C16A C17A C18A C13A -4.2(5) . . . .
C18A O3A C12A C7A -41.9(4) . . . .
C18A O3A C12A C11A 136.3(3) . . . .
C18A C13A C14A O1A 169.0(3) . . . .
C18A C13A C14A C15A -10.4(5) . . . .

_cod_database_fobs_code 4517231
