# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_mbkp_205_0m
_database_code_depnum_ccdc_archive 'CCDC 1410349'
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
# SUBMISSION DETAILS
_audit_creation_method 'manual editing of SHELXL-2013 template'
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C23 H21 P'
_chemical_formula_sum 'C23 H21 P'
_chemical_formula_weight 328.37
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'
# Crystal Data
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 21/c'
_space_group_name_Hall '-P 2ybc'
_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 8.3278(4)
_cell_length_b 17.6372(8)
_cell_length_c 12.0862(5)
_cell_angle_alpha 90
_cell_angle_beta 93.553(3)
_cell_angle_gamma 90
_cell_volume 1771.80(14)
_cell_formula_units_Z 4
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 5343
_cell_measurement_theta_min 2.31
_cell_measurement_theta_max 26.21
_exptl_crystal_description rectangular
_exptl_crystal_colour colorless
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.231
_exptl_crystal_F_000 696
_exptl_transmission_factor_min ?
_exptl_transmission_factor_max ?
_exptl_crystal_size_max 0.209
_exptl_crystal_size_mid 0.168
_exptl_crystal_size_min 0.158
_exptl_absorpt_coefficient_mu 0.155
_shelx_estimated_absorpt_T_min 0.968
_shelx_estimated_absorpt_T_max 0.976
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.7023
_exptl_absorpt_correction_T_max 0.7421
_exptl_absorpt_process_details 'SADABS v2012/1 (Apex2, Bruker AXS)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_source 'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator 'horizontal mounted graphite crystal'
_diffrn_measurement_device_type 'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method 'CCD rotation images, \f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 15480
_diffrn_reflns_av_unetI/netI 0.0382
_diffrn_reflns_av_R_equivalents 0.0299
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -22
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.045
_diffrn_reflns_theta_max 27.208
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 3945
_reflns_number_gt 2994
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
; APEX2 software package v2013.10-0 (Bruker AXS)
;
_computing_cell_refinement
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS)
;
_computing_data_reduction
; Saint V8.30A and SADABS V2012/1 (Apex2, v2013.10-0; Bruker AXS
;
_computing_structure_solution
; 'SHELXT-2014 (Sheldrick, 2014)
;
_computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics
; XP (SHELXTL-NT v6.14, Bruker AXS)
;
# REFINEMENT DATA
_refine_special_details
;The non-hydrogen atoms were refined anisotropically. Hydrogen atoms of the
phenyl- and CH-, CH~2~- and CH~3~-groups were included at geometrically
idealized positions (C-H bond distances 0.95/0.99/0.98 ) and were not
refined. The isotropic thermal parameters of these hydrogen atoms were fixed
at 1.2 (phenyl-, CH- and CH~2~-groups) and 1.5 times (CH~3~-groups) that of
the preceding carbon.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0449P)^2^+0.5900P]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 3945
_refine_ls_number_parameters 219
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0614
_refine_ls_R_factor_gt 0.0429
_refine_ls_wR_factor_ref 0.1077
_refine_ls_wR_factor_gt 0.0973
_refine_ls_goodness_of_fit_ref 1.041
_refine_ls_restrained_S_all 1.041
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
P1 P 0.39832(5) 0.23945(3) 0.60343(4) 0.02802(13) Uani 1 1 d . . . . .
C1 C 0.44646(18) 0.16736(9) 0.50173(13) 0.0258(4) Uani 1 1 d . . . . .
C2 C 0.59631(19) 0.15101(10) 0.47293(15) 0.0314(4) Uani 1 1 d . . . . .
H2 H 0.6893 0.1786 0.4986 0.038 Uiso 1 1 calc R U . . .
C3 C 0.60020(19) 0.08502(10) 0.39648(15) 0.0316(4) Uani 1 1 d . . . . .
H3A H 0.6659 0.0432 0.4299 0.038 Uiso 1 1 calc R U . . .
H3B H 0.6433 0.0996 0.3250 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3592(2) 0.00490(9) 0.31751(14) 0.0321(4) Uani 1 1 d . . . . .
C5 C 0.1940(2) -0.00541(10) 0.32047(15) 0.0376(4) Uani 1 1 d . . . . .
H5 H 0.1430 -0.0448 0.2778 0.045 Uiso 1 1 calc R U . . .
C6 C 0.1024(2) 0.04082(10) 0.38462(14) 0.0345(4) Uani 1 1 d . . . . .
H6 H -0.0099 0.0315 0.3852 0.041 Uiso 1 1 calc R U . . .
C7 C 0.16814(19) 0.10033(9) 0.44826(14) 0.0276(4) Uani 1 1 d . . . . .
C8 C 0.33469(18) 0.11146(9) 0.44612(13) 0.0248(3) Uani 1 1 d . . . . .
C9 C 0.42638(19) 0.06319(9) 0.38168(14) 0.0273(4) Uani 1 1 d . . . . .
C10 C 0.4615(3) -0.04298(11) 0.24695(16) 0.0451(5) Uani 1 1 d . . . . .
H10A H 0.5199 -0.0102 0.1977 0.068 Uiso 1 1 calc R U . . .
H10B H 0.3928 -0.0780 0.2025 0.068 Uiso 1 1 calc R U . . .
H10C H 0.5386 -0.0720 0.2947 0.068 Uiso 1 1 calc R U . . .
C11 C 0.06060(19) 0.14832(11) 0.51563(15) 0.0353(4) Uani 1 1 d . . . . .
H11A H 0.0480 0.1986 0.4817 0.053 Uiso 1 1 calc R U . . .
H11B H 0.1089 0.1535 0.5913 0.053 Uiso 1 1 calc R U . . .
H11C H -0.0450 0.1241 0.5177 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6020(2) 0.27461(10) 0.64084(14) 0.0311(4) Uani 1 1 d . . . . .
C13 C 0.6788(2) 0.24473(10) 0.73661(16) 0.0378(4) Uani 1 1 d . . . . .
H13 H 0.6209 0.2128 0.7833 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8389(2) 0.26113(12) 0.76457(18) 0.0462(5) Uani 1 1 d . . . . .
H14 H 0.8911 0.2393 0.8291 0.055 Uiso 1 1 calc R U . . .
C15 C 0.9223(2) 0.30892(12) 0.69910(19) 0.0492(5) Uani 1 1 d . . . . .
H15 H 1.0321 0.3200 0.7184 0.059 Uiso 1 1 calc R U . . .
C16 C 0.8471(2) 0.34083(12) 0.60546(18) 0.0466(5) Uani 1 1 d . . . . .
H16 H 0.9046 0.3744 0.5609 0.056 Uiso 1 1 calc R U . . .
C17 C 0.6875(2) 0.32387(11) 0.57642(16) 0.0392(4) Uani 1 1 d . . . . .
H17 H 0.6360 0.3461 0.5120 0.047 Uiso 1 1 calc R U . . .
C18 C 0.31338(18) 0.31710(9) 0.51819(14) 0.0269(4) Uani 1 1 d . . . . .
C19 C 0.2837(2) 0.38526(10) 0.57199(15) 0.0351(4) Uani 1 1 d . . . . .
H19 H 0.3123 0.3902 0.6490 0.042 Uiso 1 1 calc R U . . .
C20 C 0.2134(2) 0.44564(11) 0.51473(17) 0.0401(5) Uani 1 1 d . . . . .
H20 H 0.1968 0.4921 0.5521 0.048 Uiso 1 1 calc R U . . .
C21 C 0.1671(2) 0.43891(11) 0.40330(16) 0.0392(4) Uani 1 1 d . . . . .
H21 H 0.1172 0.4802 0.3641 0.047 Uiso 1 1 calc R U . . .
C22 C 0.1942(2) 0.37163(11) 0.34986(15) 0.0381(4) Uani 1 1 d . . . . .
H22 H 0.1618 0.3666 0.2735 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2680(2) 0.31127(10) 0.40572(14) 0.0320(4) Uani 1 1 d . . . . .
H23 H 0.2877 0.2656 0.3671 0.038 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0274(2) 0.0297(3) 0.0269(2) -0.00006(18) 0.00074(17) -0.00129(18)
C1 0.0244(8) 0.0252(9) 0.0275(9) 0.0041(7) -0.0004(6) 0.0003(6)
C2 0.0251(8) 0.0308(10) 0.0382(10) 0.0008(8) 0.0014(7) -0.0018(7)
C3 0.0273(8) 0.0295(9) 0.0385(10) 0.0050(8) 0.0066(7) 0.0050(7)
C4 0.0455(10) 0.0227(9) 0.0283(9) 0.0046(7) 0.0025(8) 0.0020(7)
C5 0.0479(11) 0.0281(10) 0.0361(11) -0.0001(8) -0.0042(8) -0.0095(8)
C6 0.0295(9) 0.0373(11) 0.0359(10) 0.0063(8) -0.0036(7) -0.0074(8)
C7 0.0255(8) 0.0278(9) 0.0293(9) 0.0063(7) -0.0003(7) 0.0000(7)
C8 0.0249(8) 0.0239(8) 0.0254(9) 0.0056(7) -0.0010(6) 0.0000(6)
C9 0.0306(8) 0.0234(9) 0.0281(9) 0.0072(7) 0.0033(7) 0.0035(7)
C10 0.0639(13) 0.0300(11) 0.0418(12) -0.0027(9) 0.0075(10) 0.0063(9)
C11 0.0234(8) 0.0428(11) 0.0398(11) 0.0026(9) 0.0021(7) 0.0003(8)
C12 0.0306(9) 0.0283(9) 0.0338(10) -0.0051(8) -0.0040(7) 0.0002(7)
C13 0.0426(11) 0.0332(10) 0.0362(11) -0.0051(8) -0.0070(8) 0.0022(8)
C14 0.0446(11) 0.0470(12) 0.0446(12) -0.0107(10) -0.0160(9) 0.0097(10)
C15 0.0304(10) 0.0488(13) 0.0671(15) -0.0209(11) -0.0095(10) 0.0012(9)
C16 0.0359(10) 0.0403(12) 0.0635(14) -0.0073(10) 0.0016(10) -0.0082(9)
C17 0.0347(10) 0.0375(11) 0.0446(12) 0.0013(9) -0.0036(8) -0.0048(8)
C18 0.0215(8) 0.0296(9) 0.0297(9) -0.0022(7) 0.0026(6) -0.0010(7)
C19 0.0371(10) 0.0343(10) 0.0335(10) -0.0082(8) -0.0017(8) 0.0029(8)
C20 0.0403(10) 0.0295(10) 0.0500(12) -0.0087(9) -0.0006(9) 0.0053(8)
C21 0.0371(10) 0.0345(11) 0.0454(12) 0.0053(9) -0.0011(8) 0.0052(8)
C22 0.0425(10) 0.0411(11) 0.0300(10) 0.0020(8) -0.0037(8) 0.0003(9)
C23 0.0365(9) 0.0296(10) 0.0300(10) -0.0034(7) 0.0025(7) 0.0016(7)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
# MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C18 1.8294(17) . ?
P1 C1 1.8301(17) . ?
P1 C12 1.8358(17) . ?
C1 C2 1.347(2) . ?
C1 C8 1.487(2) . ?
C2 C3 1.488(2) . ?
C2 H2 0.9500 . ?
C3 C9 1.498(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C9 1.385(2) . ?
C4 C5 1.390(2) . ?
C4 C10 1.502(2) . ?
C5 C6 1.386(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.403(2) . ?
C7 C11 1.507(2) . ?
C8 C9 1.410(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.391(2) . ?
C12 C17 1.392(2) . ?
C13 C14 1.385(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(3) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C23 1.392(2) . ?
C18 C19 1.396(2) . ?
C19 C20 1.380(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.376(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
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
_geom_angle_publ_flag
C18 P1 C1 103.59(7) . . ?
C18 P1 C12 101.82(8) . . ?
C1 P1 C12 99.36(7) . . ?
C2 C1 C8 107.76(14) . . ?
C2 C1 P1 124.55(13) . . ?
C8 C1 P1 127.37(11) . . ?
C1 C2 C3 112.59(15) . . ?
C1 C2 H2 123.7 . . ?
C3 C2 H2 123.7 . . ?
C2 C3 C9 102.55(13) . . ?
C2 C3 H3A 111.3 . . ?
C9 C3 H3A 111.3 . . ?
C2 C3 H3B 111.3 . . ?
C9 C3 H3B 111.3 . . ?
H3A C3 H3B 109.2 . . ?
C9 C4 C5 116.68(15) . . ?
C9 C4 C10 120.75(16) . . ?
C5 C4 C10 122.56(17) . . ?
C6 C5 C4 121.14(17) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C5 C6 C7 122.76(16) . . ?
C5 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C6 C7 C8 116.77(15) . . ?
C6 C7 C11 119.67(15) . . ?
C8 C7 C11 123.56(15) . . ?
C7 C8 C9 119.71(15) . . ?
C7 C8 C1 132.55(15) . . ?
C9 C8 C1 107.74(13) . . ?
C4 C9 C8 122.93(15) . . ?
C4 C9 C3 127.72(15) . . ?
C8 C9 C3 109.34(14) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.48(16) . . ?
C13 C12 P1 116.57(13) . . ?
C17 C12 P1 124.76(14) . . ?
C14 C13 C12 120.67(19) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.04(19) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C14 C15 C16 120.21(18) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 119.95(19) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C12 120.59(18) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C23 C18 C19 118.24(16) . . ?
C23 C18 P1 124.53(13) . . ?
C19 C18 P1 117.11(13) . . ?
C20 C19 C18 120.84(17) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C20 C21 120.40(17) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C22 C21 C20 119.15(18) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 121.01(17) . . ?
C21 C22 H22 119.5 . . ?
C23 C22 H22 119.5 . . ?
C22 C23 C18 120.34(16) . . ?
C22 C23 H23 119.8 . . ?
C18 C23 H23 119.8 . . ?
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
_geom_torsion_publ_flag
C18 P1 C1 C2 105.46(15) . . . . ?
C12 P1 C1 C2 0.78(16) . . . . ?
C18 P1 C1 C8 -81.79(15) . . . . ?
C12 P1 C1 C8 173.53(14) . . . . ?
C8 C1 C2 C3 0.58(19) . . . . ?
P1 C1 C2 C3 174.53(12) . . . . ?
C1 C2 C3 C9 0.41(19) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C10 C4 C5 C6 -178.57(17) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C11 179.79(16) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C11 C7 C8 C9 179.23(15) . . . . ?
C6 C7 C8 C1 -179.80(16) . . . . ?
C11 C7 C8 C1 -0.4(3) . . . . ?
C2 C1 C8 C7 178.27(17) . . . . ?
P1 C1 C8 C7 4.5(3) . . . . ?
C2 C1 C8 C9 -1.41(18) . . . . ?
P1 C1 C8 C9 -175.14(12) . . . . ?
C5 C4 C9 C8 -1.1(2) . . . . ?
C10 C4 C9 C8 177.62(15) . . . . ?
C5 C4 C9 C3 177.93(16) . . . . ?
C10 C4 C9 C3 -3.4(3) . . . . ?
C7 C8 C9 C4 1.1(2) . . . . ?
C1 C8 C9 C4 -179.14(15) . . . . ?
C7 C8 C9 C3 -178.05(14) . . . . ?
C1 C8 C9 C3 1.68(18) . . . . ?
C2 C3 C9 C4 179.57(16) . . . . ?
C2 C3 C9 C8 -1.30(18) . . . . ?
C18 P1 C12 C13 156.43(13) . . . . ?
C1 P1 C12 C13 -97.44(14) . . . . ?
C18 P1 C12 C17 -28.66(17) . . . . ?
C1 P1 C12 C17 77.48(17) . . . . ?
C17 C12 C13 C14 -2.7(3) . . . . ?
P1 C12 C13 C14 172.53(14) . . . . ?
C12 C13 C14 C15 1.7(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 -0.9(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 1.9(3) . . . . ?
P1 C12 C17 C16 -172.90(15) . . . . ?
C1 P1 C18 C23 12.16(15) . . . . ?
C12 P1 C18 C23 114.96(14) . . . . ?
C1 P1 C18 C19 -171.84(12) . . . . ?
C12 P1 C18 C19 -69.04(14) . . . . ?
C23 C18 C19 C20 -0.9(2) . . . . ?
P1 C18 C19 C20 -177.21(14) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C18 1.3(3) . . . . ?
C19 C18 C23 C22 -0.6(2) . . . . ?
P1 C18 C23 C22 175.40(13) . . . . ?
_refine_diff_density_max 0.310
_refine_diff_density_min -0.296
_refine_diff_density_rms 0.046
_shelxl_version_number 2012-9
_shelx_res_file
;
TITL mbkp_205_0m in P2(1)/c
CELL 0.71073 8.3278 17.6372 12.0862 90.000 93.553 90.000
ZERR 4.00 0.0004 0.0008 0.0005 0.000 0.003 0.000
LATT 1
SYMM -x, y+1/2, -z+1/2
SFAC C H P
UNIT 92 84 4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
TEMP -93.170
SIZE 0.158 0.168 0.209
ACTA
L.S. 5
OMIT -2 5 3
OMIT -3 3 4
OMIT 1 8 3
FMAP 2
PLAN -20 0 0.00
HTAB
BOND $H
CONF
WGHT 0.044900 0.590000
FVAR 0.23171
P1 3 0.398319 0.239449 0.603431 11.00000 0.02740 0.02967 =
0.02686 -0.00006 0.00074 -0.00129
C1 1 0.446459 0.167356 0.501734 11.00000 0.02440 0.02516 =
0.02746 0.00409 -0.00041 0.00025
C2 1 0.596311 0.151006 0.472926 11.00000 0.02512 0.03077 =
0.03824 0.00075 0.00139 -0.00184
AFIX 43
H2 2 0.689267 0.178588 0.498613 11.00000 -1.20000
AFIX 0
C3 1 0.600198 0.085022 0.396485 11.00000 0.02728 0.02946 =
0.03852 0.00496 0.00661 0.00500
AFIX 23
H3A 2 0.665888 0.043169 0.429923 11.00000 -1.20000
H3B 2 0.643333 0.099562 0.324982 11.00000 -1.20000
AFIX 0
C4 1 0.359163 0.004898 0.317511 11.00000 0.04546 0.02272 =
0.02826 0.00464 0.00246 0.00199
C5 1 0.194005 -0.005410 0.320467 11.00000 0.04789 0.02814 =
0.03607 -0.00008 -0.00418 -0.00950
AFIX 43
H5 2 0.143024 -0.044821 0.277775 11.00000 -1.20000
AFIX 0
C6 1 0.102415 0.040815 0.384624 11.00000 0.02954 0.03733 =
0.03591 0.00626 -0.00356 -0.00743
AFIX 43
H6 2 -0.009893 0.031524 0.385229 11.00000 -1.20000
AFIX 0
C7 1 0.168139 0.100331 0.448261 11.00000 0.02554 0.02784 =
0.02931 0.00629 -0.00028 0.00002
C8 1 0.334691 0.111459 0.446120 11.00000 0.02486 0.02385 =
0.02542 0.00558 -0.00100 0.00003
C9 1 0.426377 0.063189 0.381680 11.00000 0.03056 0.02340 =
0.02810 0.00717 0.00335 0.00350
C10 1 0.461505 -0.042979 0.246950 11.00000 0.06385 0.03002 =
0.04185 -0.00271 0.00748 0.00634
AFIX 137
H10A 2 0.519862 -0.010203 0.197708 11.00000 -1.50000
H10B 2 0.392778 -0.078009 0.202451 11.00000 -1.50000
H10C 2 0.538636 -0.071956 0.294661 11.00000 -1.50000
AFIX 0
C11 1 0.060595 0.148318 0.515625 11.00000 0.02337 0.04279 =
0.03983 0.00265 0.00209 0.00031
AFIX 137
H11A 2 0.048037 0.198592 0.481657 11.00000 -1.50000
H11B 2 0.108861 0.153506 0.591277 11.00000 -1.50000
H11C 2 -0.045038 0.124057 0.517743 11.00000 -1.50000
AFIX 0
C12 1 0.601958 0.274614 0.640835 11.00000 0.03055 0.02829 =
0.03381 -0.00513 -0.00396 0.00023
C13 1 0.678822 0.244735 0.736605 11.00000 0.04263 0.03323 =
0.03622 -0.00506 -0.00705 0.00216
AFIX 43
H13 2 0.620947 0.212763 0.783301 11.00000 -1.20000
AFIX 0
C14 1 0.838917 0.261132 0.764572 11.00000 0.04465 0.04699 =
0.04464 -0.01073 -0.01597 0.00975
AFIX 43
H14 2 0.891066 0.239310 0.829072 11.00000 -1.20000
AFIX 0
C15 1 0.922272 0.308915 0.699103 11.00000 0.03037 0.04875 =
0.06707 -0.02090 -0.00945 0.00121
AFIX 43
H15 2 1.032082 0.320020 0.718382 11.00000 -1.20000
AFIX 0
C16 1 0.847064 0.340829 0.605461 11.00000 0.03594 0.04026 =
0.06350 -0.00729 0.00162 -0.00818
AFIX 43
H16 2 0.904601 0.374411 0.560897 11.00000 -1.20000
AFIX 0
C17 1 0.687479 0.323869 0.576417 11.00000 0.03475 0.03746 =
0.04458 0.00131 -0.00359 -0.00478
AFIX 43
H17 2 0.636016 0.346066 0.511959 11.00000 -1.20000
AFIX 0
C18 1 0.313384 0.317097 0.518192 11.00000 0.02150 0.02957 =
0.02971 -0.00222 0.00264 -0.00103
C19 1 0.283736 0.385264 0.571988 11.00000 0.03711 0.03425 =
0.03354 -0.00818 -0.00167 0.00292
AFIX 43
H19 2 0.312316 0.390160 0.648977 11.00000 -1.20000
AFIX 0
C20 1 0.213418 0.445643 0.514726 11.00000 0.04026 0.02952 =
0.05005 -0.00868 -0.00057 0.00531
AFIX 43
H20 2 0.196762 0.492104 0.552096 11.00000 -1.20000
AFIX 0
C21 1 0.167074 0.438906 0.403296 11.00000 0.03709 0.03455 =
0.04539 0.00528 -0.00109 0.00522
AFIX 43
H21 2 0.117156 0.480186 0.364137 11.00000 -1.20000
AFIX 0
C22 1 0.194199 0.371634 0.349863 11.00000 0.04247 0.04113 =
0.03001 0.00203 -0.00370 0.00031
AFIX 43
H22 2 0.161787 0.366554 0.273470 11.00000 -1.20000
AFIX 0
C23 1 0.267972 0.311271 0.405723 11.00000 0.03647 0.02963 =
0.02998 -0.00337 0.00250 0.00158
AFIX 43
H23 2 0.287723 0.265625 0.367111 11.00000 -1.20000
AFIX 0
HKLF 4
REM mbkp_205_0m in P2(1)/c
REM R1 = 0.0429 for 2994 Fo > 4sig(Fo) and 0.0614 for all 3945 data
REM 219 parameters refined using 0 restraints
END
WGHT 0.0449 0.5900
REM Instructions for potential hydrogen bonds
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak 0.310, deepest hole -0.296, 1-sigma level 0.046
Q1 1 0.5083 0.2598 0.6246 11.00000 0.05 0.31
Q2 1 0.3638 0.2863 0.5587 11.00000 0.05 0.25
Q3 1 0.3722 0.1483 0.4756 11.00000 0.05 0.24
Q4 1 0.4989 0.0667 0.3921 11.00000 0.05 0.24
Q5 1 0.5230 0.1404 0.5215 11.00000 0.05 0.23
Q6 1 0.3805 0.0750 0.4328 11.00000 0.05 0.21
Q7 1 0.3245 0.3183 0.4743 11.00000 0.05 0.20
Q8 1 0.4256 0.1982 0.5446 11.00000 0.05 0.19
Q9 1 0.5020 0.1764 0.4569 11.00000 0.05 0.19
Q10 1 0.3779 0.0992 0.3841 11.00000 0.05 0.19
Q11 1 0.0448 0.1176 0.6006 11.00000 0.05 0.19
Q12 1 0.3091 0.2369 0.6639 11.00000 0.05 0.19
Q13 1 0.2484 0.1257 0.4233 11.00000 0.05 0.18
Q14 1 0.8583 0.3050 0.7458 11.00000 0.05 0.18
Q15 1 -0.0297 0.1284 0.5812 11.00000 0.05 0.18
Q16 1 0.3423 0.2200 0.6736 11.00000 0.05 0.18
Q17 1 0.6472 0.2831 0.5917 11.00000 0.05 0.17
Q18 1 0.3830 -0.0034 0.2723 11.00000 0.05 0.16
Q19 1 0.1359 0.1182 0.4945 11.00000 0.05 0.16
Q20 1 0.1509 0.2116 0.5832 11.00000 0.05 0.16
;
_shelx_res_checksum 29390
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_mb42
_database_code_depnum_ccdc_archive 'CCDC 1410416'
_audit_update_record
;
2015-07-02 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
# SUBMISSION DETAILS
_audit_creation_method 'manual editing of SHELXL-2013 template'
# CHEMICAL DATA
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C24 H23 P'
_chemical_formula_sum 'C24 H23 P'
_chemical_formula_weight 342.39
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'
# Crystal Data
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 2/c'
_space_group_name_Hall '-C 2yc'
_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 16.6549(2)
_cell_length_b 11.23230(10)
_cell_length_c 20.2304(2)
_cell_angle_alpha 90
_cell_angle_beta 96.4639(4)
_cell_angle_gamma 90
_cell_volume 3760.50(7)
_cell_formula_units_Z 8
_cell_measurement_temperature 180(2)
_cell_measurement_reflns_used 9885
_cell_measurement_theta_min 2.36
_cell_measurement_theta_max 27.27
_exptl_crystal_description block
_exptl_crystal_colour yellow
_exptl_crystal_density_meas 'not measured'
_exptl_crystal_density_method ?
_exptl_crystal_density_diffrn 1.210
_exptl_crystal_F_000 1456
_exptl_transmission_factor_min 0.6989
_exptl_transmission_factor_max 0.7455
_exptl_crystal_size_max 0.300
_exptl_crystal_size_mid 0.250
_exptl_crystal_size_min 0.200
_exptl_absorpt_coefficient_mu 0.149
_shelx_estimated_absorpt_T_min 0.957
_shelx_estimated_absorpt_T_max 0.971
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_exptl_absorpt_process_details 'SADABS v2008/1 (Apex2, Bruker AXS)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 180(2)
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'Bruker AXS K780, fine-focus sealed tube'
_diffrn_radiation_monochromator 'horizontal mounted graphite crystal'
_diffrn_measurement_device_type 'Bruker Smart Apex2 CCD (Bruker AXS)'
_diffrn_measurement_method 'CCD rotation images, \f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 27446
_diffrn_reflns_av_unetI/netI 0.0126
_diffrn_reflns_av_R_equivalents 0.0214
_diffrn_reflns_limit_h_min -21
_diffrn_reflns_limit_h_max 21
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_theta_min 2.191
_diffrn_reflns_theta_max 27.287
_diffrn_reflns_theta_full 25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total 4206
_reflns_number_gt 3857
_reflns_threshold_expression 'I > 2\s(I)'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_max .
_reflns_Friedel_fraction_full .
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection
; APEX2 software package v2008 (Bruker AXS)
;
_computing_cell_refinement
; Saint V7.68A and SADABS V2008/1 (Apex2, v2008; Bruker AXS)
;
_computing_data_reduction
; Saint V7.68A and SADABS V2008/1 (Apex2, v2008; Bruker AXS
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2012)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2012)'
_computing_molecular_graphics
; XP (SHELXTL-NT v6.14, Bruker AXS)
;
# REFINEMENT DATA
_refine_special_details
;Refinement of F^2^ against ALL reflections. The weighted R-
factor wR and goodness of fit S are based on F^2^,
conventional R-factors R are based on F, with
F set to zero for negative F^2^. The threshold expression
of F^2^ > \s(F^2^) is used only for calculating R-
factors(gt) etc. and is not relevant to the choice of reflections
for refinement. R-factors based on F^2^ are statistically
about twice as large as those based on F, and R- factors
based on ALL data will be even larger.
The non-hydrogen atoms were refined anisotropically. Hydrogen atoms of the
phenyl- and CH~3~-groups were included at geometrically idealized positions
(C-H bond distances 0.95/0.99 ) and were not refined.
The isotropicthermal parameters of these hydrogen atoms were fixed
at 1.2 (phenyl groups) and 1.5 times (CH~3~-groups) that of
the preceding carbon atom, respectively.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.0544P)^2^+2.2679P]
where P=(Fo^2^+2Fc^2^)/3
;
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef .
_refine_ls_number_reflns 4206
_refine_ls_number_parameters 229
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0371
_refine_ls_R_factor_gt 0.0341
_refine_ls_wR_factor_ref 0.0968
_refine_ls_wR_factor_gt 0.0934
_refine_ls_goodness_of_fit_ref 1.024
_refine_ls_restrained_S_all 1.024
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
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
P1 P 0.18659(2) 0.03965(3) 0.01954(2) 0.02617(10) Uani 1 1 d . . . . .
C1 C 0.13579(7) 0.16546(10) 0.04118(6) 0.0275(2) Uani 1 1 d . . . . .
C2 C 0.07190(7) 0.21550(10) -0.00410(6) 0.0294(2) Uani 1 1 d . . . . .
H2 H 0.0577 0.1899 -0.0486 0.035 Uiso 1 1 calc R U . . .
C3 C 0.03460(7) 0.30553(11) 0.02637(6) 0.0303(2) Uani 1 1 d . . . . .
H3 H -0.0090 0.3526 0.0066 0.036 Uiso 1 1 calc R U . . .
C4 C 0.05487(7) 0.39395(11) 0.14431(6) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.10105(8) 0.38370(12) 0.20516(6) 0.0384(3) Uani 1 1 d . . . . .
H5 H 0.0908 0.4353 0.2405 0.046 Uiso 1 1 calc R U . . .
C6 C 0.16264(8) 0.29874(12) 0.21574(6) 0.0364(3) Uani 1 1 d . . . . .
H6 H 0.1929 0.2944 0.2584 0.044 Uiso 1 1 calc R U . . .
C7 C 0.18146(7) 0.22076(11) 0.16680(6) 0.0307(2) Uani 1 1 d . . . . .
C8 C 0.13567(7) 0.22918(10) 0.10338(5) 0.0271(2) Uani 1 1 d . . . . .
C9 C 0.07243(7) 0.31665(10) 0.09293(6) 0.0287(2) Uani 1 1 d . . . . .
C10 C -0.01481(9) 0.47988(13) 0.13271(7) 0.0442(3) Uani 1 1 d . . . . .
H10A H -0.0091 0.5276 0.0930 0.066 Uiso 1 1 calc R U . . .
H10B H -0.0150 0.5326 0.1713 0.066 Uiso 1 1 calc R U . . .
H10C H -0.0657 0.4354 0.1263 0.066 Uiso 1 1 calc R U . . .
C11 C 0.24992(8) 0.13397(12) 0.18260(6) 0.0382(3) Uani 1 1 d . . . . .
H11A H 0.2330 0.0548 0.1662 0.057 Uiso 1 1 calc R U . . .
H11B H 0.2645 0.1306 0.2309 0.057 Uiso 1 1 calc R U . . .
H11C H 0.2967 0.1601 0.1611 0.057 Uiso 1 1 calc R U . . .
C12 C 0.29478(7) 0.05256(12) 0.02218(7) 0.0370(3) Uani 1 1 d . . . . .
H12A H 0.3166 -0.0199 0.0039 0.056 Uiso 1 1 calc R U . . .
H12B H 0.3186 0.0631 0.0684 0.056 Uiso 1 1 calc R U . . .
H12C H 0.3080 0.1214 -0.0043 0.056 Uiso 1 1 calc R U . . .
C13 C 0.15210(7) 0.00355(10) -0.06581(5) 0.0273(2) Uani 1 1 d . . . . .
C14 C 0.18165(7) 0.06976(11) -0.11634(6) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.2197 0.1317 -0.1054 0.040 Uiso 1 1 calc R U . . .
C15 C 0.15547(8) 0.04495(11) -0.18238(6) 0.0363(3) Uani 1 1 d . . . . .
H15 H 0.1749 0.0909 -0.2166 0.044 Uiso 1 1 calc R U . . .
C16 C 0.10104(8) -0.04655(11) -0.19862(6) 0.0351(3) Uani 1 1 d . . . . .
H16 H 0.0837 -0.0638 -0.2440 0.042 Uiso 1 1 calc R U . . .
C17 C 0.07184(7) -0.11298(12) -0.14878(6) 0.0354(3) Uani 1 1 d . . . . .
H17 H 0.0345 -0.1756 -0.1600 0.042 Uiso 1 1 calc R U . . .
C18 C 0.09710(7) -0.08815(11) -0.08228(6) 0.0311(2) Uani 1 1 d . . . . .
H18 H 0.0769 -0.1336 -0.0482 0.037 Uiso 1 1 calc R U . . .
C19 C 0.16694(7) -0.08720(10) 0.07049(5) 0.0278(2) Uani 1 1 d . . . . .
C20 C 0.21818(8) -0.18567(12) 0.07700(6) 0.0373(3) Uani 1 1 d . . . . .
H20 H 0.2653 -0.1874 0.0545 0.045 Uiso 1 1 calc R U . . .
C21 C 0.20038(10) -0.28107(12) 0.11628(7) 0.0444(3) Uani 1 1 d . . . . .
H21 H 0.2352 -0.3483 0.1206 0.053 Uiso 1 1 calc R U . . .
C22 C 0.13199(9) -0.27870(12) 0.14927(7) 0.0428(3) Uani 1 1 d . . . . .
H22 H 0.1196 -0.3447 0.1757 0.051 Uiso 1 1 calc R U . . .
C23 C 0.08166(8) -0.18068(13) 0.14391(7) 0.0403(3) Uani 1 1 d . . . . .
H23 H 0.0352 -0.1788 0.1672 0.048 Uiso 1 1 calc R U . . .
C24 C 0.09894(7) -0.08467(11) 0.10441(6) 0.0332(3) Uani 1 1 d . . . . .
H24 H 0.0642 -0.0173 0.1006 0.040 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.02292(15) 0.02771(16) 0.02740(16) 0.00391(10) 0.00072(11) -0.00391(10)
C1 0.0263(5) 0.0270(5) 0.0284(5) 0.0041(4) -0.0010(4) -0.0039(4)
C2 0.0254(5) 0.0326(6) 0.0289(5) 0.0062(4) -0.0019(4) -0.0059(4)
C3 0.0231(5) 0.0334(6) 0.0341(6) 0.0100(5) 0.0014(4) -0.0027(4)
C4 0.0337(6) 0.0327(6) 0.0370(6) 0.0071(5) 0.0115(5) -0.0028(5)
C5 0.0468(7) 0.0379(7) 0.0322(6) 0.0003(5) 0.0121(5) -0.0038(5)
C6 0.0419(7) 0.0407(7) 0.0262(6) 0.0043(5) 0.0023(5) -0.0070(5)
C7 0.0308(6) 0.0315(6) 0.0291(6) 0.0061(4) 0.0003(4) -0.0061(5)
C8 0.0258(5) 0.0267(5) 0.0287(5) 0.0057(4) 0.0024(4) -0.0060(4)
C9 0.0250(5) 0.0294(5) 0.0322(6) 0.0081(4) 0.0058(4) -0.0050(4)
C10 0.0456(8) 0.0421(7) 0.0474(8) 0.0080(6) 0.0164(6) 0.0072(6)
C11 0.0391(7) 0.0400(7) 0.0329(6) 0.0035(5) -0.0080(5) 0.0004(5)
C12 0.0233(5) 0.0463(7) 0.0411(7) 0.0044(5) 0.0020(5) -0.0053(5)
C13 0.0253(5) 0.0290(5) 0.0277(5) 0.0021(4) 0.0031(4) -0.0020(4)
C14 0.0348(6) 0.0322(6) 0.0335(6) 0.0040(5) 0.0037(5) -0.0083(5)
C15 0.0386(7) 0.0407(7) 0.0303(6) 0.0068(5) 0.0069(5) -0.0031(5)
C16 0.0337(6) 0.0417(7) 0.0298(6) -0.0030(5) 0.0030(5) 0.0013(5)
C17 0.0311(6) 0.0371(6) 0.0379(6) -0.0049(5) 0.0036(5) -0.0073(5)
C18 0.0283(5) 0.0330(6) 0.0329(6) 0.0019(5) 0.0069(4) -0.0053(5)
C19 0.0291(5) 0.0281(5) 0.0252(5) 0.0027(4) -0.0014(4) -0.0032(4)
C20 0.0426(7) 0.0350(6) 0.0343(6) 0.0027(5) 0.0047(5) 0.0060(5)
C21 0.0586(9) 0.0313(6) 0.0417(7) 0.0066(5) -0.0017(6) 0.0070(6)
C22 0.0516(8) 0.0372(7) 0.0362(7) 0.0138(5) -0.0093(6) -0.0123(6)
C23 0.0336(6) 0.0502(8) 0.0361(7) 0.0125(6) -0.0004(5) -0.0109(6)
C24 0.0274(6) 0.0363(6) 0.0353(6) 0.0072(5) 0.0006(5) -0.0026(5)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
# MOLECULAR GEOMETRY
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C1 1.7285(12) . ?
P1 C12 1.8024(12) . ?
P1 C13 1.8034(11) . ?
P1 C19 1.8099(11) . ?
C1 C2 1.4380(15) . ?
C1 C8 1.4477(16) . ?
C2 C3 1.3692(17) . ?
C2 H2 0.9500 . ?
C3 C9 1.4265(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3809(18) . ?
C4 C9 1.4100(17) . ?
C4 C10 1.5074(18) . ?
C5 C6 1.3998(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3840(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4200(16) . ?
C7 C11 1.5068(17) . ?
C8 C9 1.4385(16) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.3937(16) . ?
C13 C14 1.3978(16) . ?
C14 C15 1.3861(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3852(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3859(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.3918(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C24 1.3891(16) . ?
C19 C20 1.3942(17) . ?
C20 C21 1.3858(19) . ?
C20 H20 0.9500 . ?
C21 C22 1.384(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.3914(17) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
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
_geom_angle_publ_flag
C1 P1 C12 116.29(6) . . ?
C1 P1 C13 108.30(5) . . ?
C12 P1 C13 104.84(6) . . ?
C1 P1 C19 111.98(5) . . ?
C12 P1 C19 106.90(6) . . ?
C13 P1 C19 108.04(5) . . ?
C2 C1 C8 106.68(10) . . ?
C2 C1 P1 120.43(9) . . ?
C8 C1 P1 132.29(9) . . ?
C3 C2 C1 110.04(10) . . ?
C3 C2 H2 125.0 . . ?
C1 C2 H2 125.0 . . ?
C2 C3 C9 108.36(10) . . ?
C2 C3 H3 125.8 . . ?
C9 C3 H3 125.8 . . ?
C5 C4 C9 117.70(11) . . ?
C5 C4 C10 122.27(12) . . ?
C9 C4 C10 119.97(12) . . ?
C4 C5 C6 121.20(12) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C7 C6 C5 122.90(11) . . ?
C7 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
C6 C7 C8 117.54(11) . . ?
C6 C7 C11 118.98(11) . . ?
C8 C7 C11 123.46(11) . . ?
C7 C8 C9 119.21(11) . . ?
C7 C8 C1 134.37(11) . . ?
C9 C8 C1 106.42(10) . . ?
C4 C9 C3 130.06(11) . . ?
C4 C9 C8 121.43(11) . . ?
C3 C9 C8 108.49(10) . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
P1 C12 H12A 109.5 . . ?
P1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
P1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.63(11) . . ?
C18 C13 P1 121.67(9) . . ?
C14 C13 P1 118.70(9) . . ?
C15 C14 C13 119.97(11) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C16 C15 C14 120.28(11) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 120.05(12) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.19(11) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 119.88(11) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?
C24 C19 C20 119.61(11) . . ?
C24 C19 P1 118.36(9) . . ?
C20 C19 P1 122.03(9) . . ?
C21 C20 C19 119.96(12) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.17(13) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.19(12) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.02(13) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 120.04(12) . . ?
C19 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
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
_geom_torsion_publ_flag
C12 P1 C1 C2 123.68(9) . . . . ?
C13 P1 C1 C2 6.01(10) . . . . ?
C19 P1 C1 C2 -113.02(9) . . . . ?
C12 P1 C1 C8 -66.50(12) . . . . ?
C13 P1 C1 C8 175.83(10) . . . . ?
C19 P1 C1 C8 56.80(12) . . . . ?
C8 C1 C2 C3 0.89(12) . . . . ?
P1 C1 C2 C3 173.04(8) . . . . ?
C1 C2 C3 C9 -0.54(13) . . . . ?
C9 C4 C5 C6 -0.64(18) . . . . ?
C10 C4 C5 C6 176.48(12) . . . . ?
C4 C5 C6 C7 0.25(19) . . . . ?
C5 C6 C7 C8 0.23(18) . . . . ?
C5 C6 C7 C11 178.83(12) . . . . ?
C6 C7 C8 C9 -0.28(15) . . . . ?
C11 C7 C8 C9 -178.82(10) . . . . ?
C6 C7 C8 C1 -179.28(12) . . . . ?
C11 C7 C8 C1 2.2(2) . . . . ?
C2 C1 C8 C7 178.21(12) . . . . ?
P1 C1 C8 C7 7.4(2) . . . . ?
C2 C1 C8 C9 -0.87(11) . . . . ?
P1 C1 C8 C9 -171.72(9) . . . . ?
C5 C4 C9 C3 178.79(11) . . . . ?
C10 C4 C9 C3 1.61(18) . . . . ?
C5 C4 C9 C8 0.57(16) . . . . ?
C10 C4 C9 C8 -176.61(11) . . . . ?
C2 C3 C9 C4 -178.43(11) . . . . ?
C2 C3 C9 C8 -0.03(12) . . . . ?
C7 C8 C9 C4 -0.12(16) . . . . ?
C1 C8 C9 C4 179.14(10) . . . . ?
C7 C8 C9 C3 -178.68(10) . . . . ?
C1 C8 C9 C3 0.57(12) . . . . ?
C1 P1 C13 C18 -102.33(10) . . . . ?
C12 P1 C13 C18 132.90(10) . . . . ?
C19 P1 C13 C18 19.16(11) . . . . ?
C1 P1 C13 C14 77.67(11) . . . . ?
C12 P1 C13 C14 -47.10(11) . . . . ?
C19 P1 C13 C14 -160.84(10) . . . . ?
C18 C13 C14 C15 0.77(19) . . . . ?
P1 C13 C14 C15 -179.23(10) . . . . ?
C13 C14 C15 C16 -1.0(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C15 C16 C17 C18 -0.06(19) . . . . ?
C16 C17 C18 C13 -0.19(19) . . . . ?
C14 C13 C18 C17 -0.16(18) . . . . ?
P1 C13 C18 C17 179.84(9) . . . . ?
C1 P1 C19 C24 19.48(11) . . . . ?
C12 P1 C19 C24 147.94(10) . . . . ?
C13 P1 C19 C24 -99.70(10) . . . . ?
C1 P1 C19 C20 -159.84(10) . . . . ?
C12 P1 C19 C20 -31.39(12) . . . . ?
C13 P1 C19 C20 80.97(11) . . . . ?
C24 C19 C20 C21 1.06(19) . . . . ?
P1 C19 C20 C21 -179.62(10) . . . . ?
C19 C20 C21 C22 -0.2(2) . . . . ?
C20 C21 C22 C23 -0.8(2) . . . . ?
C21 C22 C23 C24 1.0(2) . . . . ?
C20 C19 C24 C23 -0.86(18) . . . . ?
P1 C19 C24 C23 179.80(9) . . . . ?
C22 C23 C24 C19 -0.17(19) . . . . ?
_refine_diff_density_max 0.300
_refine_diff_density_min -0.279
_refine_diff_density_rms 0.046
_shelxl_version_number 2012-9
_shelx_res_file
;
TITL mb42 in C2/c - Revised April 30, 2014
CELL 0.71073 16.6549 11.2323 20.2304 90.000 96.4639 90.000
ZERR 8.00 0.0002 0.0001 0.0002 0.000 0.0004 0.000
LATT 7
SYMM -X, Y, 0.5-Z
SFAC C H P
UNIT 192 184 8
LIST 4
CONF
ACTA
OMIT 4 0 10
OMIT -1 3 8
OMIT -6 2 1
BOND $H
L.S. 5
FMAP 2
PLAN 20
SIZE 0.20 0.25 0.30
TEMP -93.180
WGHT 0.054400 2.267900
FVAR 0.08162
P1 3 0.186594 0.039653 0.019541 11.00000 0.02292 0.02771 =
0.02740 0.00391 0.00072 -0.00391
C1 1 0.135792 0.165459 0.041181 11.00000 0.02628 0.02699 =
0.02842 0.00412 -0.00105 -0.00394
C2 1 0.071902 0.215502 -0.004097 11.00000 0.02541 0.03263 =
0.02895 0.00624 -0.00189 -0.00587
AFIX 43
H2 2 0.057665 0.189859 -0.048623 11.00000 -1.20000
AFIX 0
C3 1 0.034596 0.305528 0.026372 11.00000 0.02311 0.03342 =
0.03409 0.00998 0.00138 -0.00273
AFIX 43
H3 2 -0.009046 0.352565 0.006560 11.00000 -1.20000
AFIX 0
C4 1 0.054868 0.393948 0.144313 11.00000 0.03368 0.03269 =
0.03703 0.00709 0.01151 -0.00279
C5 1 0.101046 0.383703 0.205162 11.00000 0.04676 0.03791 =
0.03215 0.00032 0.01210 -0.00378
AFIX 43
H5 2 0.090827 0.435257 0.240491 11.00000 -1.20000
AFIX 0
C6 1 0.162640 0.298738 0.215737 11.00000 0.04189 0.04066 =
0.02623 0.00433 0.00227 -0.00699
AFIX 43
H6 2 0.192860 0.294411 0.258391 11.00000 -1.20000
AFIX 0
C7 1 0.181455 0.220759 0.166799 11.00000 0.03081 0.03148 =
0.02911 0.00615 0.00035 -0.00613
C8 1 0.135674 0.229183 0.103375 11.00000 0.02576 0.02673 =
0.02867 0.00572 0.00241 -0.00599
C9 1 0.072430 0.316652 0.092934 11.00000 0.02503 0.02938 =
0.03216 0.00812 0.00581 -0.00498
C10 1 -0.014814 0.479884 0.132712 11.00000 0.04556 0.04205 =
0.04741 0.00797 0.01640 0.00724
AFIX 137
H10A 2 -0.009077 0.527578 0.092953 11.00000 -1.50000
H10B 2 -0.014953 0.532553 0.171319 11.00000 -1.50000
H10C 2 -0.065712 0.435390 0.126323 11.00000 -1.50000
AFIX 0
C11 1 0.249916 0.133975 0.182602 11.00000 0.03911 0.03996 =
0.03285 0.00351 -0.00797 0.00039
AFIX 137
H11A 2 0.232990 0.054776 0.166156 11.00000 -1.50000
H11B 2 0.264541 0.130646 0.230862 11.00000 -1.50000
H11C 2 0.296743 0.160058 0.161065 11.00000 -1.50000
AFIX 0
C12 1 0.294780 0.052560 0.022182 11.00000 0.02335 0.04628 =
0.04109 0.00443 0.00197 -0.00530
AFIX 137
H12A 2 0.316562 -0.019866 0.003901 11.00000 -1.50000
H12B 2 0.318557 0.063133 0.068362 11.00000 -1.50000
H12C 2 0.308042 0.121430 -0.004279 11.00000 -1.50000
AFIX 0
C13 1 0.152100 0.003550 -0.065805 11.00000 0.02530 0.02901 =
0.02766 0.00212 0.00312 -0.00201
C14 1 0.181648 0.069763 -0.116343 11.00000 0.03479 0.03225 =
0.03346 0.00400 0.00370 -0.00829
AFIX 43
H14 2 0.219651 0.131742 -0.105438 11.00000 -1.20000
AFIX 0
C15 1 0.155471 0.044946 -0.182378 11.00000 0.03862 0.04070 =
0.03029 0.00679 0.00688 -0.00311
AFIX 43
H15 2 0.174940 0.090884 -0.216642 11.00000 -1.20000
AFIX 0
C16 1 0.101044 -0.046549 -0.198624 11.00000 0.03372 0.04167 =
0.02981 -0.00300 0.00303 0.00128
AFIX 43
H16 2 0.083725 -0.063775 -0.243967 11.00000 -1.20000
AFIX 0
C17 1 0.071840 -0.112977 -0.148777 11.00000 0.03114 0.03708 =
0.03786 -0.00492 0.00365 -0.00732
AFIX 43
H17 2 0.034475 -0.175633 -0.160029 11.00000 -1.20000
AFIX 0
C18 1 0.097100 -0.088151 -0.082278 11.00000 0.02828 0.03301 =
0.03286 0.00190 0.00688 -0.00529
AFIX 43
H18 2 0.076887 -0.133632 -0.048178 11.00000 -1.20000
AFIX 0
C19 1 0.166938 -0.087201 0.070489 11.00000 0.02906 0.02811 =
0.02523 0.00273 -0.00136 -0.00316
C20 1 0.218184 -0.185672 0.077001 11.00000 0.04261 0.03501 =
0.03428 0.00265 0.00474 0.00597
AFIX 43
H20 2 0.265276 -0.187372 0.054528 11.00000 -1.20000
AFIX 0
C21 1 0.200384 -0.281066 0.116277 11.00000 0.05862 0.03125 =
0.04175 0.00663 -0.00173 0.00696
AFIX 43
H21 2 0.235224 -0.348258 0.120563 11.00000 -1.20000
AFIX 0
C22 1 0.131993 -0.278705 0.149269 11.00000 0.05164 0.03723 =
0.03618 0.01379 -0.00927 -0.01231
AFIX 43
H22 2 0.119636 -0.344720 0.175683 11.00000 -1.20000
AFIX 0
C23 1 0.081664 -0.180680 0.143910 11.00000 0.03357 0.05025 =
0.03614 0.01247 -0.00042 -0.01089
AFIX 43
H23 2 0.035228 -0.178785 0.167194 11.00000 -1.20000
AFIX 0
C24 1 0.098938 -0.084669 0.104415 11.00000 0.02743 0.03627 =
0.03530 0.00722 0.00063 -0.00256
AFIX 43
H24 2 0.064204 -0.017339 0.100648 11.00000 -1.20000
AFIX 0
HKLF 4
REM mb42 in C2/c - Revised April 30, 2014
REM R1 = 0.0341 for 3857 Fo > 4sig(Fo) and 0.0371 for all 4206 data
REM 229 parameters refined using 0 restraints
END
WGHT 0.0544 2.2666
REM Highest difference peak 0.300, deepest hole -0.279, 1-sigma level 0.046
Q1 1 0.2461 0.0441 0.0215 11.00000 0.05 0.30
Q2 1 0.1666 0.0229 -0.0270 11.00000 0.05 0.29
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