#------------------------------------------------------------------------------
#$Date: 2017-05-25 08:30:31 +0300 (Thu, 25 May 2017) $
#$Revision: 196973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/61/1546115.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1546115
loop_
_publ_author_name
'Krause, Lennard'
'Niepötter, Benedikt'
'Schürmann, Christian J.'
'Stalke, Dietmar'
'Herbst-Irmer, Regine'
_publ_section_title
;
 Validation of experimental charge-density refinement strategies: when do
 we overfit?
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052252517005103
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C20 H23 P S'
_chemical_formula_sum            'C20 H23 P S'
_chemical_formula_weight         326.41
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.9323(7)
_cell_length_b                   14.5698(10)
_cell_length_c                   21.0910(14)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    99(2)
_cell_measurement_theta_max      52.1495
_cell_measurement_theta_min      2.6835
_cell_volume                     3359.4(4)
_computing_cell_refinement       'SAINT V8.37A'
_computing_data_collection       'APEX2 v2012.2'
_computing_data_reduction        'SAINT V8.37A'
_computing_molecular_graphics    'XP Version 5.1'
_computing_publication_material  'XP Version 5.1'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX II Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            222190
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         52.228
_diffrn_reflns_theta_min         1.931
_diffrn_source                   'BRUKER Rotating Anode'
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  0.9285
_exptl_absorpt_correction_T_min  0.8845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.600
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         19329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0238
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0508P)²+0.0744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0839
_refine_ls_wR_factor_ref         0.0904
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15462
_reflns_number_total             19329
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            lc5072.cif
_cod_data_source_block           2_shelx
_cod_database_code               1546115
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
P1 P 0.43671(2) 0.29822(2) 0.56327(2) 0.00922(2) Uani 1 1 d . .
S1 S 0.60402(2) 0.33080(2) 0.53581(2) 0.01521(2) Uani 1 1 d . .
C1 C 0.40206(3) 0.31454(2) 0.64870(2) 0.01034(4) Uani 1 1 d . .
C2 C 0.30308(3) 0.26463(2) 0.67638(2) 0.01075(4) Uani 1 1 d . .
C4 C 0.11899(3) 0.16839(3) 0.66988(2) 0.01492(5) Uani 1 1 d . .
H4 H 0.058349 0.139171 0.644711 0.018 Uiso 1 1 calc R U
C3 C 0.20688(3) 0.22113(2) 0.64096(2) 0.01242(4) Uani 1 1 d . .
H3 H 0.204017 0.229091 0.596281 0.015 Uiso 1 1 calc R U
C6 C 0.20005(3) 0.20333(3) 0.77300(2) 0.01496(5) Uani 1 1 d . .
H6 H 0.195897 0.198935 0.817888 0.018 Uiso 1 1 calc R U
C5 C 0.11708(3) 0.15670(3) 0.73686(2) 0.01648(5) Uani 1 1 d . .
H5 H 0.058972 0.117058 0.756143 0.020 Uiso 1 1 calc R U
C9 C 0.46281(3) 0.36539(2) 0.75644(2) 0.01249(4) Uani 1 1 d . .
C8 C 0.37449(3) 0.30767(2) 0.78264(2) 0.01384(4) Uani 1 1 d . .
H8 H 0.369591 0.301534 0.827413 0.017 Uiso 1 1 calc R U
C7 C 0.29318(3) 0.25872(2) 0.74445(2) 0.01205(4) Uani 1 1 d . .
C10 C 0.54052(4) 0.41836(3) 0.79718(2) 0.01576(5) Uani 1 1 d . .
H10 H 0.532674 0.412301 0.841845 0.019 Uiso 1 1 calc R U
C11 C 0.62554(4) 0.47733(3) 0.77299(2) 0.01712(5) Uani 1 1 d . .
H11 H 0.677982 0.510914 0.800405 0.021 Uiso 1 1 calc R U
C12 C 0.63443(4) 0.48772(3) 0.70613(2) 0.01678(5) Uani 1 1 d . .
H12 H 0.690985 0.530669 0.689118 0.020 Uiso 1 1 calc R U
C13 C 0.56309(3) 0.43705(2) 0.66565(2) 0.01450(5) Uani 1 1 d . .
H13 H 0.571264 0.446018 0.621240 0.017 Uiso 1 1 calc R U
C14 C 0.47650(3) 0.37091(2) 0.68854(2) 0.01117(4) Uani 1 1 d . .
C15 C 0.41687(3) 0.17399(2) 0.54644(2) 0.01192(4) Uani 1 1 d . .
H15 H 0.331068 0.156393 0.557495 0.014 Uiso 1 1 calc R U
C16 C 0.43759(4) 0.15348(3) 0.47599(2) 0.01605(5) Uani 1 1 d . .
H16A H 0.519861 0.173469 0.463738 0.024 Uiso 1 1 calc R U
H16C H 0.376730 0.186496 0.450617 0.024 Uiso 1 1 calc R U
H16B H 0.429444 0.087369 0.468551 0.024 Uiso 1 1 calc R U
C17 C 0.50405(4) 0.11832(3) 0.58809(2) 0.01940(6) Uani 1 1 d . .
H17A H 0.486521 0.130758 0.632838 0.029 Uiso 1 1 calc R U
H17C H 0.588664 0.135782 0.578596 0.029 Uiso 1 1 calc R U
H17B H 0.492851 0.052749 0.579522 0.029 Uiso 1 1 calc R U
C18 C 0.31688(3) 0.36258(2) 0.51945(2) 0.01225(4) Uani 1 1 d . .
H18 H 0.243807 0.321749 0.515231 0.015 Uiso 1 1 calc R U
C19 C 0.35876(4) 0.38913(3) 0.45265(2) 0.01911(6) Uani 1 1 d . .
H19A H 0.432669 0.426977 0.455445 0.029 Uiso 1 1 calc R U
H19B H 0.293831 0.423951 0.431486 0.029 Uiso 1 1 calc R U
H19C H 0.376578 0.333465 0.428258 0.029 Uiso 1 1 calc R U
C20 C 0.27772(4) 0.44846(3) 0.55624(2) 0.01955(6) Uani 1 1 d . .
H20A H 0.245183 0.430371 0.597694 0.029 Uiso 1 1 calc R U
H20B H 0.214382 0.481141 0.532330 0.029 Uiso 1 1 calc R U
H20C H 0.348555 0.488766 0.562210 0.029 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'
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
C1 P1 C15 106.649(14)
C1 P1 C18 105.929(14)
C15 P1 C18 108.335(15)
C1 P1 S1 116.260(11)
C15 P1 S1 106.626(11)
C18 P1 S1 112.682(12)
C2 C1 C14 118.92(3)
C2 C1 P1 119.08(2)
C14 C1 P1 121.87(2)
C1 C2 C3 124.49(3)
C1 C2 C7 119.61(3)
C3 C2 C7 115.86(3)
C3 C4 C5 121.21(3)
C3 C4 H4 119.4
C5 C4 H4 119.4
C4 C3 C2 121.86(3)
C4 C3 H3 119.1
C2 C3 H3 119.1
C5 C6 C7 121.20(3)
C5 C6 H6 119.4
C7 C6 H6 119.4
C6 C5 C4 118.99(3)
C6 C5 H5 120.5
C4 C5 H5 120.5
C8 C9 C10 119.82(3)
C8 C9 C14 119.94(3)
C10 C9 C14 120.24(3)
C9 C8 C7 121.36(3)
C9 C8 H8 119.3
C7 C8 H8 119.3
C8 C7 C6 119.89(3)
C8 C7 C2 119.75(3)
C6 C7 C2 120.36(3)
C11 C10 C9 121.22(3)
C11 C10 H10 119.4
C9 C10 H10 119.4
C10 C11 C12 118.98(3)
C10 C11 H11 120.5
C12 C11 H11 120.5
C13 C12 C11 121.40(3)
C13 C12 H12 119.3
C11 C12 H12 119.3
C12 C13 C14 121.82(3)
C12 C13 H13 119.1
C14 C13 H13 119.1
C1 C14 C13 124.34(3)
C1 C14 C9 119.51(3)
C13 C14 C9 116.11(3)
C17 C15 C16 111.19(3)
C17 C15 P1 109.54(2)
C16 C15 P1 110.98(2)
C17 C15 H15 108.3
C16 C15 H15 108.3
P1 C15 H15 108.3
C15 C16 H16A 109.5
C15 C16 H16C 109.5
H16A C16 H16C 109.5
C15 C16 H16B 109.5
H16A C16 H16B 109.5
H16C C16 H16B 109.5
C15 C17 H17A 109.5
C15 C17 H17C 109.5
H17A C17 H17C 109.5
C15 C17 H17B 109.5
H17A C17 H17B 109.5
H17C C17 H17B 109.5
C19 C18 C20 110.06(3)
C19 C18 P1 112.00(2)
C20 C18 P1 110.92(2)
C19 C18 H18 107.9
C20 C18 H18 107.9
P1 C18 H18 107.9
C18 C19 H19A 109.5
C18 C19 H19B 109.5
H19A C19 H19B 109.5
C18 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C18 C20 H20A 109.5
C18 C20 H20B 109.5
H20A C20 H20B 109.5
C18 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
P1 C1 1.8565(3)
P1 C15 1.8572(3)
P1 C18 1.8573(3)
P1 S1 1.97648(16)
C1 C2 1.4285(4)
C1 C14 1.4292(4)
C2 C3 1.4373(4)
C2 C7 1.4423(4)
C4 C3 1.3732(5)
C4 C5 1.4230(5)
C4 H4 0.9500
C3 H3 0.9500
C6 C5 1.3658(5)
C6 C7 1.4319(5)
C6 H6 0.9500
C5 H5 0.9500
C9 C8 1.3946(5)
C9 C10 1.4338(5)
C9 C14 1.4421(4)
C8 C7 1.3955(5)
C8 H8 0.9500
C10 C11 1.3647(6)
C10 H10 0.9500
C11 C12 1.4215(5)
C11 H11 0.9500
C12 C13 1.3719(5)
C12 H12 0.9500
C13 C14 1.4345(5)
C13 H13 0.9500
C15 C17 1.5290(5)
C15 C16 1.5325(5)
C15 H15 1.0000
C16 H16A 0.9800
C16 H16C 0.9800
C16 H16B 0.9800
C17 H17A 0.9800
C17 H17C 0.9800
C17 H17B 0.9800
C18 C19 1.5310(5)
C18 C20 1.5334(5)
C18 H18 1.0000
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
