#------------------------------------------------------------------------------
#$Date: 2019-12-21 00:05:56 +0200 (Sat, 21 Dec 2019) $
#$Revision: 245449 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/72/4517241.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_4517241
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 P S'
_chemical_formula_sum            'C18 H9 O3 P S'
_chemical_formula_weight         336.28
_chemical_name_common            'phosphangulene sulfide'
_chemical_name_systematic
'4,8,12-Trioxa-12c-phosphadibenzo[cd,mn]pyrene 12c-sulfide'
_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   difmap
_atom_sites_solution_primary     direct
_audit_contact_author_name
;
;
_audit_creation_date             2018-11-12
_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                   14.7446(3)
_cell_length_b                   13.0971(3)
_cell_length_c                   14.9443(3)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    105
_cell_measurement_theta_max      63.538
_cell_measurement_theta_min      3.905
_cell_volume                     2885.92(11)
_computing_cell_refinement
;
SAINT (2013) V8.34A; 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) V8.34A; 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      105
_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 0.996
_diffrn_measured_fraction_theta_max 0.995
_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  0.0274
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            30130
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.554
_diffrn_reflns_theta_min         4.697
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    2.049
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.6898
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0941 before and 0.0399 after correction.
The Ratio of minimum to maximum transmission is 0.9169.
The λ/2 correction factor is 0.00150.
;
_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    1.548
_exptl_crystal_description       Block
_exptl_crystal_F_000             1376
_exptl_crystal_recrystallization_method
'Crystallized in EtOH (with small traces of THF)'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3574
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0306
_refine_ls_R_factor_gt           0.0294
_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)+(0.0503P)²+1.2666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0847
_refine_ls_wR_factor_ref         0.0857
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3406
_reflns_number_total             3574
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            phangs_b_jw1821.cif
_cod_data_source_block           jw1821
_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_database_code               4517241
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
S1A S 0.36693(2) 0.13616(2) 0.62319(2) 0.01970(9) Uani 1 1 d . . . . .
P1A P 0.43127(2) 0.26506(2) 0.61960(2) 0.01322(9) Uani 1 1 d . . . . .
O1A O 0.54704(6) 0.29932(7) 0.78196(5) 0.02309(18) Uani 1 1 d . . . . .
O2A O 0.30024(6) 0.43742(7) 0.60766(6) 0.0261(2) Uani 1 1 d . . . . .
O3A O 0.55517(6) 0.27898(7) 0.46056(5) 0.02213(18) Uani 1 1 d . . . . .
C1A C 0.41239(7) 0.35695(8) 0.70312(7) 0.0181(2) Uani 1 1 d . . . . .
C2A C 0.47054(8) 0.36206(9) 0.77632(7) 0.0207(2) Uani 1 1 d . . . . .
C3A C 0.45374(10) 0.43241(10) 0.84390(8) 0.0288(3) Uani 1 1 d . . . . .
H3A H 0.4913(12) 0.4348(14) 0.8929(11) 0.030(4) Uiso 1 1 d . . . . .
C4A C 0.38131(10) 0.49998(10) 0.83250(10) 0.0326(3) Uani 1 1 d . . . . .
H4A H 0.3731(14) 0.5520(18) 0.8804(12) 0.048(6) Uiso 1 1 d . . . . .
C5A C 0.32903(9) 0.50334(10) 0.75528(10) 0.0298(3) Uani 1 1 d . . . . .
H5A H 0.2841(11) 0.5542(13) 0.7474(11) 0.033(4) Uiso 1 1 d . . . . .
C6A C 0.34696(7) 0.43218(9) 0.68891(9) 0.0222(2) Uani 1 1 d . . . . .
C7A C 0.41724(7) 0.34578(8) 0.52686(7) 0.0168(2) Uani 1 1 d . . . . .
C8A C 0.35021(7) 0.42090(9) 0.52950(8) 0.0213(2) Uani 1 1 d . . . . .
C9A C 0.33368(9) 0.47961(9) 0.45414(10) 0.0291(3) Uani 1 1 d . . . . .
H9A H 0.2852(12) 0.5298(14) 0.4579(11) 0.037(5) Uiso 1 1 d . . . . .
C10A C 0.38910(11) 0.46576(10) 0.38004(9) 0.0310(3) Uani 1 1 d . . . . .
H10A H 0.3769(12) 0.5050(15) 0.3241(12) 0.042(5) Uiso 1 1 d . . . . .
C11A C 0.46365(10) 0.40007(10) 0.38016(8) 0.0267(3) Uani 1 1 d . . . . .
H11A H 0.5042(13) 0.3966(15) 0.3334(14) 0.047(5) Uiso 1 1 d . . . . .
C12A C 0.47846(8) 0.34107(9) 0.45615(7) 0.0195(2) Uani 1 1 d . . . . .
C13A C 0.55030(8) 0.26657(8) 0.62239(7) 0.0148(2) Uani 1 1 d . . . . .
C14A C 0.59469(8) 0.27786(8) 0.70407(7) 0.0180(2) Uani 1 1 d . . . . .
C15A C 0.68859(8) 0.27025(9) 0.70739(9) 0.0243(3) Uani 1 1 d . . . . .
H15A H 0.7184(12) 0.2743(13) 0.7604(12) 0.032(4) Uiso 1 1 d . . . . .
C16A C 0.73528(9) 0.25825(10) 0.62715(9) 0.0274(3) Uani 1 1 d . . . . .
H16A H 0.8023(14) 0.2542(14) 0.6289(10) 0.037(5) Uiso 1 1 d . . . . .
C17A C 0.69249(8) 0.25982(9) 0.54414(9) 0.0241(3) Uani 1 1 d . . . . .
H17A H 0.7267(11) 0.2608(13) 0.4929(11) 0.030(4) Uiso 1 1 d . . . . .
C18A C 0.59853(8) 0.26749(8) 0.54228(8) 0.0178(2) 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 0.0140 0.0070 '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 0.0390 0.0250 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2540 0.3350 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.2920 0.4250 '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
C1A P1A S1A 119.99(4) . .
C7A P1A S1A 119.28(4) . .
C7A P1A C1A 97.45(6) . .
C7A P1A C13A 97.45(5) . .
C13A P1A S1A 119.91(4) . .
C13A P1A C1A 97.70(5) . .
C14A O1A C2A 118.47(8) . .
C6A O2A C8A 117.30(9) . .
C18A O3A C12A 118.61(8) . .
C2A C1A P1A 119.60(9) . .
C2A C1A C6A 120.78(10) . .
C6A C1A P1A 119.04(9) . .
C1A C2A O1A 121.08(10) . .
C3A C2A O1A 119.32(11) . .
C3A C2A C1A 119.57(12) . .
C2A C3A H3A 119.7(11) . .
C2A C3A C4A 117.88(13) . .
C4A C3A H3A 122.4(11) . .
C3A C4A H4A 116.0(12) . .
C5A C4A C3A 123.06(12) . .
C5A C4A H4A 120.6(12) . .
C4A C5A H5A 120.9(10) . .
C6A C5A C4A 117.87(12) . .
C6A C5A H5A 121.2(10) . .
C1A C6A O2A 120.51(10) . .
C5A C6A O2A 119.64(11) . .
C5A C6A C1A 119.84(12) . .
C8A C7A P1A 119.07(9) . .
C12A C7A P1A 119.78(8) . .
C12A C7A C8A 120.82(10) . .
C7A C8A O2A 120.41(10) . .
C9A C8A O2A 120.04(11) . .
C9A C8A C7A 119.55(12) . .
C8A C9A H9A 117.3(10) . .
C8A C9A C10A 118.19(12) . .
C10A C9A H9A 124.5(10) . .
C9A C10A H10A 119.6(11) . .
C9A C10A C11A 122.90(11) . .
C11A C10A H10A 117.5(11) . .
C10A C11A H11A 122.7(13) . .
C12A C11A C10A 117.84(12) . .
C12A C11A H11A 119.4(13) . .
C7A C12A O3A 121.07(10) . .
C11A C12A O3A 119.33(11) . .
C11A C12A C7A 119.59(11) . .
C14A C13A P1A 119.45(8) . .
C18A C13A P1A 119.35(8) . .
C18A C13A C14A 120.84(11) . .
O1A C14A C13A 121.23(10) . .
O1A C14A C15A 119.27(10) . .
C15A C14A C13A 119.47(11) . .
C14A C15A H15A 120.7(11) . .
C14A C15A C16A 118.06(11) . .
C16A C15A H15A 121.3(11) . .
C15A C16A H16A 118.5(9) . .
C15A C16A C17A 122.83(11) . .
C17A C16A H16A 118.4(9) . .
C16A C17A H17A 119.6(10) . .
C18A C17A C16A 118.09(11) . .
C18A C17A H17A 122.1(10) . .
O3A C18A C13A 121.52(10) . .
O3A C18A C17A 119.03(10) . .
C17A C18A C13A 119.43(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1A P1A 1.9373(4) .
P1A C1A 1.7561(11) .
P1A C7A 1.7553(11) .
P1A C13A 1.7556(12) .
O1A C2A 1.3982(15) .
O1A C14A 1.3884(14) .
O2A C6A 1.3977(15) .
O2A C8A 1.3978(15) .
O3A C12A 1.3947(14) .
O3A C18A 1.3866(14) .
C1A C2A 1.3915(16) .
C1A C6A 1.3951(16) .
C2A C3A 1.3892(16) .
C3A H3A 0.919(17) .
C3A C4A 1.397(2) .
C4A H4A 1.00(2) .
C4A C5A 1.389(2) .
C5A H5A 0.947(17) .
C5A C6A 1.3864(17) .
C7A C8A 1.3952(15) .
C7A C12A 1.3911(16) .
C8A C9A 1.3853(17) .
C9A H9A 0.973(18) .
C9A C10A 1.388(2) .
C10A H10A 0.997(19) .
C10A C11A 1.396(2) .
C11A H11A 0.92(2) .
C11A C12A 1.3908(16) .
C13A C14A 1.3930(14) .
C13A C18A 1.3924(15) .
C14A C15A 1.3891(16) .
C15A H15A 0.908(18) .
C15A C16A 1.3915(19) .
C16A H16A 0.99(2) .
C16A C17A 1.3919(18) .
C17A H17A 0.917(17) .
C17A C18A 1.3894(16) .
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
S1A P1A C1A C2A 95.70(9) . . . .
S1A P1A C1A C6A -92.90(9) . . . .
S1A P1A C7A C8A 92.20(9) . . . .
S1A P1A C7A C12A -94.34(9) . . . .
S1A P1A C13A C14A -94.04(9) . . . .
S1A P1A C13A C18A 92.81(9) . . . .
P1A C1A C2A O1A 3.90(14) . . . .
P1A C1A C2A C3A -177.78(9) . . . .
P1A C1A C6A O2A -3.12(15) . . . .
P1A C1A C6A C5A 177.89(9) . . . .
P1A C7A C8A O2A 5.46(14) . . . .
P1A C7A C8A C9A -174.88(9) . . . .
P1A C7A C12A O3A -5.15(14) . . . .
P1A C7A C12A C11A 175.61(9) . . . .
P1A C13A C14A O1A -7.27(14) . . . .
P1A C13A C14A C15A 174.47(9) . . . .
P1A C13A C18A O3A 7.47(14) . . . .
P1A C13A C18A C17A -174.49(8) . . . .
O1A C2A C3A C4A 174.52(11) . . . .
O1A C14A C15A C16A -174.08(10) . . . .
O2A C8A C9A C10A 175.47(11) . . . .
C1A P1A C7A C8A -38.44(10) . . . .
C1A P1A C7A C12A 135.02(9) . . . .
C1A P1A C13A C14A 37.24(10) . . . .
C1A P1A C13A C18A -135.91(9) . . . .
C1A C2A C3A C4A -3.83(17) . . . .
C2A O1A C14A C13A -34.88(14) . . . .
C2A O1A C14A C15A 143.38(11) . . . .
C2A C1A C6A O2A 168.17(10) . . . .
C2A C1A C6A C5A -10.81(17) . . . .
C2A C3A C4A C5A -3.51(19) . . . .
C3A C4A C5A C6A 3.70(19) . . . .
C4A C5A C6A O2A -175.54(11) . . . .
C4A C5A C6A C1A 3.45(17) . . . .
C6A O2A C8A C7A 39.51(15) . . . .
C6A O2A C8A C9A -140.16(11) . . . .
C6A C1A C2A O1A -167.35(10) . . . .
C6A C1A C2A C3A 10.98(17) . . . .
C7A P1A C1A C2A -134.13(9) . . . .
C7A P1A C1A C6A 37.26(10) . . . .
C7A P1A C13A C14A 135.85(9) . . . .
C7A P1A C13A C18A -37.30(9) . . . .
C7A C8A C9A C10A -4.20(17) . . . .
C8A O2A C6A C1A -40.82(15) . . . .
C8A O2A C6A C5A 138.17(11) . . . .
C8A C7A C12A O3A 168.19(10) . . . .
C8A C7A C12A C11A -11.05(16) . . . .
C8A C9A C10A C11A -3.97(19) . . . .
C9A C10A C11A C12A 4.63(19) . . . .
C10A C11A C12A O3A -176.36(11) . . . .
C10A C11A C12A C7A 2.89(17) . . . .
C12A O3A C18A C13A 34.23(14) . . . .
C12A O3A C18A C17A -143.81(10) . . . .
C12A C7A C8A O2A -167.93(10) . . . .
C12A C7A C8A C9A 11.74(16) . . . .
C13A P1A C1A C2A -35.52(10) . . . .
C13A P1A C1A C6A 135.87(9) . . . .
C13A P1A C7A C8A -137.26(9) . . . .
C13A P1A C7A C12A 36.20(10) . . . .
C13A C14A C15A C16A 4.22(16) . . . .
C14A O1A C2A C1A 36.75(15) . . . .
C14A O1A C2A C3A -141.57(11) . . . .
C14A C13A C18A O3A -165.59(10) . . . .
C14A C13A C18A C17A 12.45(16) . . . .
C14A C15A C16A C17A 4.00(18) . . . .
C15A C16A C17A C18A -4.03(18) . . . .
C16A C17A C18A O3A 173.91(10) . . . .
C16A C17A C18A C13A -4.18(16) . . . .
C18A O3A C12A C7A -35.49(14) . . . .
C18A O3A C12A C11A 143.75(11) . . . .
C18A C13A C14A O1A 165.78(10) . . . .
C18A C13A C14A C15A -12.48(16) . . . .

_cod_database_fobs_code 4517241
