# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_compound1a
_database_code_depnum_ccdc_archive 'CCDC 1886029'
loop_
_audit_author_name
_audit_author_address
'Akihiro Tsurusaki'
;Osaka Prefecture University
Japan
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7


#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        dibenzo[b,e]phosphindolizine-P-oxide
_chemical_name_common            ?
_chemical_melting_point          '210-211 \%C.'
_chemical_formula_moiety         'C16 H11 O P'
_chemical_formula_sum            'C16 H11 O P'
_chemical_formula_weight         250.22

#==============================================================================

_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                   11.341(4)
_cell_length_b                   9.571(3)
_cell_length_c                   11.845(4)
_cell_angle_alpha                90
_cell_angle_beta                 112.200(5)
_cell_angle_gamma                90
_cell_volume                     1190.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    3937
_cell_measurement_theta_min      3.0034
_cell_measurement_theta_max      27.4816

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.213
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9353
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

#==============================================================================

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14228
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.482
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997

#==============================================================================
# REFINEMENT DATA

_reflns_number_total             2720
_reflns_number_gt                2403
_reflns_threshold_expression     'I > 2σ(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.
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.5295P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2720
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0898
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.052

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'
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'

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  
'SHELXL-2014/7 and Yadokari-XG 2009 (Kabuto et al., 2009)'

#==============================================================================

# 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 0.68077(3) 0.72606(4) 0.69527(3) 0.01583(12) Uani 1 1 d . . . . .
O1 O 0.71207(10) 0.85731(11) 0.76792(9) 0.0208(2) Uani 1 1 d . . . . .
C1 C 0.52986(13) 0.73030(15) 0.56858(13) 0.0176(3) Uani 1 1 d . . . . .
C16 C 0.81436(13) 0.66067(14) 0.66668(13) 0.0174(3) Uani 1 1 d . . . . .
C15 C 0.84777(14) 0.70968(15) 0.57232(13) 0.0193(3) Uani 1 1 d . . . . .
H15 H 0.7932 0.7731 0.5142 0.023 Uiso 1 1 calc R U . . .
C2 C 0.48347(14) 0.82246(16) 0.47195(13) 0.0210(3) Uani 1 1 d . . . . .
H2 H 0.5382 0.8897 0.4583 0.025 Uiso 1 1 calc R U . . .
C8 C 0.63765(15) 0.57331(15) 0.75900(13) 0.0212(3) Uani 1 1 d . . . . .
C6 C 0.44921(14) 0.63093(15) 0.59067(14) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.51419(15) 0.54044(16) 0.69639(14) 0.0234(3) Uani 1 1 d . . . . .
H7 H 0.4728 0.4652 0.7188 0.028 Uiso 1 1 calc R U . . .
C14 C 0.96073(14) 0.66639(16) 0.56242(14) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.9821 0.6978 0.4964 0.028 Uiso 1 1 calc R U . . .
C5 C 0.32161(14) 0.62535(17) 0.51358(15) 0.0247(3) Uani 1 1 d . . . . .
H5 H 0.2663 0.5588 0.5273 0.030 Uiso 1 1 calc R U . . .
C4 C 0.27542(15) 0.71852(17) 0.41579(15) 0.0265(3) Uani 1 1 d . . . . .
H4 H 0.1882 0.7151 0.3632 0.032 Uiso 1 1 calc R U . . .
C11 C 0.89393(14) 0.56526(15) 0.75363(13) 0.0205(3) Uani 1 1 d . . . . .
C12 C 1.00923(14) 0.52772(16) 0.74371(14) 0.0251(3) Uani 1 1 d . . . . .
H12 H 1.0661 0.4671 0.8029 0.030 Uiso 1 1 calc R U . . .
C13 C 1.04190(14) 0.57709(17) 0.64959(15) 0.0263(3) Uani 1 1 d . . . . .
H13 H 1.1203 0.5497 0.6446 0.032 Uiso 1 1 calc R U . . .
C3 C 0.35496(15) 0.81575(18) 0.39441(14) 0.0258(3) Uani 1 1 d . . . . .
H3 H 0.3224 0.8779 0.3272 0.031 Uiso 1 1 calc R U . . .
C9 C 0.73915(16) 0.49445(16) 0.84869(14) 0.0257(3) Uani 1 1 d . . . . .
H9 H 0.7224 0.4411 0.9086 0.031 Uiso 1 1 calc R U . . .
C10 C 0.85730(16) 0.49692(16) 0.84697(14) 0.0255(3) Uani 1 1 d . . . . .
H10 H 0.9226 0.4506 0.9116 0.031 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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.
;

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 O1 1.4880(11) . ?
P1 C16 1.7859(15) . ?
P1 C8 1.7960(16) . ?
P1 C1 1.8005(15) . ?
C1 C2 1.382(2) . ?
C1 C6 1.411(2) . ?
C16 C15 1.390(2) . ?
C16 C11 1.417(2) . ?
C15 C14 1.393(2) . ?
C2 C3 1.400(2) . ?
C8 C7 1.351(2) . ?
C8 C9 1.449(2) . ?
C6 C5 1.390(2) . ?
C6 C7 1.471(2) . ?
C14 C13 1.388(2) . ?
C5 C4 1.397(2) . ?
C4 C3 1.384(2) . ?
C11 C12 1.403(2) . ?
C11 C10 1.473(2) . ?
C12 C13 1.384(2) . ?
C9 C10 1.348(2) . ?

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
O1 P1 C16 111.80(6) . . ?
O1 P1 C8 119.18(7) . . ?
C16 P1 C8 100.35(7) . . ?
O1 P1 C1 114.01(6) . . ?
C16 P1 C1 117.21(7) . . ?
C8 P1 C1 92.56(7) . . ?
C2 C1 C6 120.89(14) . . ?
C2 C1 P1 130.47(11) . . ?
C6 C1 P1 108.00(11) . . ?
C15 C16 C11 120.64(13) . . ?
C15 C16 P1 122.86(11) . . ?
C11 C16 P1 116.18(11) . . ?
C16 C15 C14 120.40(14) . . ?
C1 C2 C3 119.35(14) . . ?
C7 C8 C9 130.74(15) . . ?
C7 C8 P1 110.44(11) . . ?
C9 C8 P1 117.73(12) . . ?
C5 C6 C1 119.40(14) . . ?
C5 C6 C7 126.79(14) . . ?
C1 C6 C7 113.80(13) . . ?
C8 C7 C6 114.34(13) . . ?
C13 C14 C15 119.56(15) . . ?
C6 C5 C4 119.42(14) . . ?
C3 C4 C5 120.97(14) . . ?
C12 C11 C16 117.52(14) . . ?
C12 C11 C10 119.02(14) . . ?
C16 C11 C10 123.30(14) . . ?
C13 C12 C11 121.44(14) . . ?
C12 C13 C14 120.35(14) . . ?
C4 C3 C2 119.97(15) . . ?
C10 C9 C8 119.91(14) . . ?
C9 C10 C11 125.66(14) . . ?

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
O1 P1 C1 C2 55.75(16) . . . . ?
C16 P1 C1 C2 -77.59(16) . . . . ?
C8 P1 C1 C2 179.40(14) . . . . ?
O1 P1 C1 C6 -114.91(10) . . . . ?
C16 P1 C1 C6 111.75(11) . . . . ?
C8 P1 C1 C6 8.74(11) . . . . ?
O1 P1 C16 C15 -82.68(13) . . . . ?
C8 P1 C16 C15 149.96(12) . . . . ?
C1 P1 C16 C15 51.63(14) . . . . ?
O1 P1 C16 C11 90.88(12) . . . . ?
C8 P1 C16 C11 -36.49(12) . . . . ?
C1 P1 C16 C11 -134.82(11) . . . . ?
C11 C16 C15 C14 -0.5(2) . . . . ?
P1 C16 C15 C14 172.78(11) . . . . ?
C6 C1 C2 C3 -0.7(2) . . . . ?
P1 C1 C2 C3 -170.32(12) . . . . ?
O1 P1 C8 C7 112.66(11) . . . . ?
C16 P1 C8 C7 -125.04(11) . . . . ?
C1 P1 C8 C7 -6.78(12) . . . . ?
O1 P1 C8 C9 -77.98(13) . . . . ?
C16 P1 C8 C9 44.32(13) . . . . ?
C1 P1 C8 C9 162.58(12) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
P1 C1 C6 C5 172.13(11) . . . . ?
C2 C1 C6 C7 179.50(13) . . . . ?
P1 C1 C6 C7 -8.77(15) . . . . ?
C9 C8 C7 C6 -164.62(15) . . . . ?
P1 C8 C7 C6 2.91(16) . . . . ?
C5 C6 C7 C8 -176.94(14) . . . . ?
C1 C6 C7 C8 4.04(18) . . . . ?
C16 C15 C14 C13 -1.9(2) . . . . ?
C1 C6 C5 C4 -0.2(2) . . . . ?
C7 C6 C5 C4 -179.15(14) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C15 C16 C11 C12 2.8(2) . . . . ?
P1 C16 C11 C12 -170.94(11) . . . . ?
C15 C16 C11 C10 -172.66(14) . . . . ?
P1 C16 C11 C10 13.63(19) . . . . ?
C16 C11 C12 C13 -2.7(2) . . . . ?
C10 C11 C12 C13 172.92(14) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C15 C14 C13 C12 2.0(2) . . . . ?
C5 C4 C3 C2 -0.5(2) . . . . ?
C1 C2 C3 C4 0.8(2) . . . . ?
C7 C8 C9 C10 139.64(17) . . . . ?
P1 C8 C9 C10 -27.2(2) . . . . ?
C8 C9 C10 C11 -5.4(2) . . . . ?
C12 C11 C10 C9 -162.36(15) . . . . ?
C16 C11 C10 C9 13.0(2) . . . . ?

#==============================================================================

####################################################################### 
# 
# 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_compound1c
_database_code_depnum_ccdc_archive 'CCDC 1886031'
loop_
_audit_author_name
_audit_author_address
'Akihiro Tsurusaki'
;Osaka Prefecture University
Japan
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        dibenzo[b,e]phosphindolizine-P-selenide
_chemical_name_common            ?
_chemical_melting_point          '201-205 \%C.'
_chemical_formula_moiety         'C16 H11 P Se'
_chemical_formula_sum            'C16 H11 P Se'
_chemical_formula_weight         313.18

#==============================================================================

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0608(4)
_cell_length_b                   12.8843(8)
_cell_length_c                   27.9209(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2540.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6127
_cell_measurement_theta_min      3.1623
_cell_measurement_theta_max      27.4778

#==============================================================================

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    3.058
_shelx_estimated_absorpt_T_min   0.540
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8164
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

#==============================================================================

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            23815
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996

#==============================================================================
# REFINEMENT DATA

_reflns_number_total             2892
_reflns_number_gt                2673
_reflns_threshold_expression     'I > 2σ(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.
;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0357P)²+2.0517P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2892
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0714
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.794
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.074

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'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  
'SHELXL-2014/7 and Yadokari-XG 2009 (Kabuto et al., 2009)'

#==============================================================================

# 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
Se1 Se 0.50559(2) 0.40636(2) 0.36391(2) 0.01824(8) Uani 1 1 d . . . . .
P1 P 0.22183(6) 0.37452(4) 0.38246(2) 0.01458(11) Uani 1 1 d . . . . .
C11 C -0.0153(2) 0.39409(16) 0.30490(7) 0.0167(4) Uani 1 1 d . . . . .
C1 C 0.1819(2) 0.37050(14) 0.44648(6) 0.0154(3) Uani 1 1 d . . . . .
C10 C 0.0149(3) 0.28300(16) 0.29469(7) 0.0196(4) Uani 1 1 d . . . . .
H10 H -0.0131 0.2594 0.2632 0.024 Uiso 1 1 calc R U . . .
C4 C 0.1495(3) 0.31629(16) 0.54204(6) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.1391 0.2982 0.5749 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1990(3) 0.41692(16) 0.52949(7) 0.0210(4) Uani 1 1 d . . . . .
H3 H 0.2200 0.4672 0.5538 0.025 Uiso 1 1 calc R U . . .
C14 C -0.0948(3) 0.60584(15) 0.32210(7) 0.0204(4) Uani 1 1 d . . . . .
H14 H -0.1236 0.6767 0.3281 0.024 Uiso 1 1 calc R U . . .
C12 C -0.1250(3) 0.45244(16) 0.27294(6) 0.0196(4) Uani 1 1 d . . . . .
H12 H -0.1725 0.4204 0.2447 0.024 Uiso 1 1 calc R U . . .
C2 C 0.2182(3) 0.44469(15) 0.48140(6) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.2554 0.5130 0.4727 0.022 Uiso 1 1 calc R U . . .
C5 C 0.1149(3) 0.24124(16) 0.50706(6) 0.0189(4) Uani 1 1 d . . . . .
H5 H 0.0806 0.1726 0.5160 0.023 Uiso 1 1 calc R U . . .
C7 C 0.0991(3) 0.19999(15) 0.41728(7) 0.0180(4) Uani 1 1 d . . . . .
H7 H 0.0584 0.1300 0.4205 0.022 Uiso 1 1 calc R U . . .
C16 C 0.0569(3) 0.44557(15) 0.34584(6) 0.0159(3) Uani 1 1 d . . . . .
C13 C -0.1659(3) 0.55623(16) 0.28165(7) 0.0211(4) Uani 1 1 d . . . . .
H13 H -0.2431 0.5937 0.2598 0.025 Uiso 1 1 calc R U . . .
C6 C 0.1312(2) 0.26825(15) 0.45869(6) 0.0172(4) Uani 1 1 d . . . . .
C9 C 0.0789(3) 0.21226(15) 0.32634(7) 0.0202(4) Uani 1 1 d . . . . .
H9 H 0.0892 0.1414 0.3173 0.024 Uiso 1 1 calc R U . . .
C15 C 0.0191(3) 0.55023(16) 0.35355(7) 0.0178(4) Uani 1 1 d . . . . .
H15 H 0.0718 0.5841 0.3807 0.021 Uiso 1 1 calc R U . . .
C8 C 0.1321(2) 0.24491(15) 0.37426(7) 0.0168(4) Uani 1 1 d . . . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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.
;

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
Se1 P1 2.1097(5) . ?
P1 C16 1.8001(19) . ?
P1 C8 1.8006(19) . ?
P1 C1 1.8104(18) . ?
C11 C12 1.401(3) . ?
C11 C16 1.416(3) . ?
C11 C10 1.475(3) . ?
C1 C2 1.389(3) . ?
C1 C6 1.407(3) . ?
C10 C9 1.348(3) . ?
C4 C3 1.388(3) . ?
C4 C5 1.396(3) . ?
C3 C2 1.396(3) . ?
C14 C15 1.390(3) . ?
C14 C13 1.392(3) . ?
C12 C13 1.389(3) . ?
C5 C6 1.399(2) . ?
C7 C8 1.353(3) . ?
C7 C6 1.470(3) . ?
C16 C15 1.391(3) . ?
C9 C8 1.452(3) . ?

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
C16 P1 C8 99.89(9) . . ?
C16 P1 C1 118.33(8) . . ?
C8 P1 C1 92.53(9) . . ?
C16 P1 Se1 112.10(6) . . ?
C8 P1 Se1 118.89(6) . . ?
C1 P1 Se1 113.32(6) . . ?
C12 C11 C16 117.51(18) . . ?
C12 C11 C10 118.54(17) . . ?
C16 C11 C10 123.94(18) . . ?
C2 C1 C6 121.41(16) . . ?
C2 C1 P1 130.13(14) . . ?
C6 C1 P1 107.80(13) . . ?
C9 C10 C11 125.33(18) . . ?
C3 C4 C5 120.98(17) . . ?
C4 C3 C2 120.44(18) . . ?
C15 C14 C13 119.00(19) . . ?
C13 C12 C11 121.34(17) . . ?
C1 C2 C3 118.73(18) . . ?
C4 C5 C6 119.23(18) . . ?
C8 C7 C6 114.55(17) . . ?
C15 C16 C11 120.64(17) . . ?
C15 C16 P1 121.94(14) . . ?
C11 C16 P1 116.94(14) . . ?
C12 C13 C14 120.60(18) . . ?
C5 C6 C1 119.19(17) . . ?
C5 C6 C7 126.69(18) . . ?
C1 C6 C7 114.12(16) . . ?
C10 C9 C8 119.67(18) . . ?
C14 C15 C16 120.86(18) . . ?
C7 C8 C9 130.48(18) . . ?
C7 C8 P1 110.15(14) . . ?
C9 C8 P1 118.48(14) . . ?

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
C16 P1 C1 C2 -78.20(19) . . . . ?
C8 P1 C1 C2 179.14(18) . . . . ?
Se1 P1 C1 C2 56.06(19) . . . . ?
C16 P1 C1 C6 111.27(14) . . . . ?
C8 P1 C1 C6 8.61(14) . . . . ?
Se1 P1 C1 C6 -114.47(12) . . . . ?
C12 C11 C10 C9 -164.34(18) . . . . ?
C16 C11 C10 C9 14.3(3) . . . . ?
C5 C4 C3 C2 -1.0(3) . . . . ?
C16 C11 C12 C13 -1.7(3) . . . . ?
C10 C11 C12 C13 177.03(17) . . . . ?
C6 C1 C2 C3 -1.6(3) . . . . ?
P1 C1 C2 C3 -171.00(15) . . . . ?
C4 C3 C2 C1 1.7(3) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C10 C11 C16 C15 -178.65(17) . . . . ?
C12 C11 C16 P1 -172.29(13) . . . . ?
C10 C11 C16 P1 9.1(2) . . . . ?
C8 P1 C16 C15 155.42(16) . . . . ?
C1 P1 C16 C15 57.08(18) . . . . ?
Se1 P1 C16 C15 -77.70(16) . . . . ?
C8 P1 C16 C11 -32.44(16) . . . . ?
C1 P1 C16 C11 -130.78(14) . . . . ?
Se1 P1 C16 C11 94.44(14) . . . . ?
C11 C12 C13 C14 1.5(3) . . . . ?
C15 C14 C13 C12 0.5(3) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 -179.59(17) . . . . ?
C2 C1 C6 C5 0.8(3) . . . . ?
P1 C1 C6 C5 172.31(14) . . . . ?
C2 C1 C6 C7 -179.65(16) . . . . ?
P1 C1 C6 C7 -8.13(19) . . . . ?
C8 C7 C6 C5 -177.46(18) . . . . ?
C8 C7 C6 C1 3.0(2) . . . . ?
C11 C10 C9 C8 -2.8(3) . . . . ?
C13 C14 C15 C16 -2.2(3) . . . . ?
C11 C16 C15 C14 2.0(3) . . . . ?
P1 C16 C15 C14 173.82(15) . . . . ?
C6 C7 C8 C9 -164.96(19) . . . . ?
C6 C7 C8 P1 3.8(2) . . . . ?
C10 C9 C8 C7 138.1(2) . . . . ?
C10 C9 C8 P1 -29.9(2) . . . . ?
C16 P1 C8 C7 -126.54(14) . . . . ?
C1 P1 C8 C7 -7.20(14) . . . . ?
Se1 P1 C8 C7 111.29(13) . . . . ?
C16 P1 C8 C9 43.76(16) . . . . ?
C1 P1 C8 C9 163.10(15) . . . . ?
Se1 P1 C8 C9 -78.41(15) . . . . ?

#==============================================================================

####################################################################### 
# 
# 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_compound1d
_database_code_depnum_ccdc_archive 'CCDC 1886032'
loop_
_audit_author_name
_audit_author_address
'Akihiro Tsurusaki'
;Osaka Prefecture University
Japan
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        dibenzo[b,e]phosphindolizine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H11 P'
_chemical_formula_sum            'C16 H11 P'
_chemical_formula_weight         234.22


_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.174(3)
_cell_length_b                   7.276(2)
_cell_length_c                   11.608(4)
_cell_angle_alpha                90
_cell_angle_beta                 106.916(5)
_cell_angle_gamma                90
_cell_volume                     579.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    2082
_cell_measurement_theta_min      3.0008
_cell_measurement_theta_max      27.4778

#==============================================================================

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9157
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

#==============================================================================

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            4756
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.001
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.982

#==============================================================================
# REFINEMENT DATA

_reflns_number_total             2573
_reflns_number_gt                2415
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.831
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.975

_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.
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2573
_refine_ls_number_parameters     154
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0864
_refine_ls_wR_factor_gt          0.0854
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.052

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'

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  
'SHELXL-2014/7 and Yadokari-XG 2009 (Kabuto et al., 2009)'

#==============================================================================

# 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 0.64984(8) 0.36337(8) 0.81205(5) 0.01737(17) Uani 1 1 d . . . . .
C15 C 0.5080(3) 0.3685(4) 1.0140(2) 0.0228(5) Uani 1 1 d . . . . .
H15 H 0.3881 0.3233 0.9629 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5329(4) 0.3892(4) 1.1371(2) 0.0277(6) Uani 1 1 d . . . . .
H14 H 0.4289 0.3612 1.1694 0.033 Uiso 1 1 calc R U . . .
C6 C 0.5480(4) 0.5957(3) 0.6310(2) 0.0241(6) Uani 1 1 d . . . . .
C12 C 0.8604(4) 0.4921(4) 1.1661(2) 0.0275(6) Uani 1 1 d . . . . .
H12 H 0.9809 0.5330 1.2188 0.033 Uiso 1 1 calc R U . . .
C11 C 0.8396(4) 0.4750(3) 1.0427(2) 0.0222(5) Uani 1 1 d . . . . .
C1 C 0.4599(4) 0.4771(4) 0.6971(2) 0.0201(5) Uani 1 1 d . . . . .
C16 C 0.6576(4) 0.4135(3) 0.9662(2) 0.0191(5) Uani 1 1 d . . . . .
C5 C 0.4324(5) 0.6738(4) 0.5244(2) 0.0325(7) Uani 1 1 d . . . . .
H5 H 0.4899 0.7513 0.4783 0.039 Uiso 1 1 calc R U . . .
C10 C 1.0067(4) 0.5190(4) 0.9998(3) 0.0321(6) Uani 1 1 d . . . . .
H10 H 1.1288 0.5312 1.0595 0.039 Uiso 1 1 calc R U . . .
C9 C 1.0064(4) 0.5438(4) 0.8862(3) 0.0326(7) Uani 1 1 d . . . . .
H9 H 1.1235 0.5730 0.8676 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7094(5) 0.4506(4) 1.2120(2) 0.0315(7) Uani 1 1 d . . . . .
H13 H 0.7261 0.4641 1.2958 0.038 Uiso 1 1 calc R U . . .
C2 C 0.2614(4) 0.4388(4) 0.6552(2) 0.0269(6) Uani 1 1 d . . . . .
H2 H 0.2036 0.3553 0.6976 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7560(5) 0.6237(4) 0.6872(3) 0.0321(7) Uani 1 1 d . . . . .
H7 H 0.8346 0.7012 0.6546 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2333(5) 0.6388(4) 0.4852(2) 0.0354(7) Uani 1 1 d . . . . .
H4 H 0.1550 0.6939 0.4132 0.043 Uiso 1 1 calc R U . . .
C8 C 0.8266(4) 0.5257(4) 0.7926(3) 0.0275(6) Uani 1 1 d . . . . .
C3 C 0.1485(4) 0.5235(4) 0.5512(2) 0.0335(7) Uani 1 1 d . . . . .
H3 H 0.0119 0.5024 0.5248 0.040 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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.
;

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 C8 1.794(3) . ?
P1 C1 1.806(3) . ?
P1 C16 1.811(3) . ?
C15 C16 1.383(4) . ?
C15 C14 1.396(3) . ?
C14 C13 1.385(4) . ?
C6 C5 1.395(4) . ?
C6 C1 1.420(4) . ?
C6 C7 1.459(4) . ?
C12 C13 1.373(4) . ?
C12 C11 1.402(4) . ?
C11 C16 1.421(3) . ?
C11 C10 1.461(4) . ?
C1 C2 1.393(4) . ?
C5 C4 1.391(5) . ?
C10 C9 1.331(4) . ?
C9 C8 1.430(4) . ?
C2 C3 1.387(4) . ?
C7 C8 1.379(4) . ?
C4 C3 1.390(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
_geom_angle_publ_flag
C8 P1 C1 90.83(13) . . ?
C8 P1 C16 99.90(12) . . ?
C1 P1 C16 115.92(11) . . ?
C16 C15 C14 120.1(2) . . ?
C13 C14 C15 119.9(3) . . ?
C5 C6 C1 119.0(3) . . ?
C5 C6 C7 127.4(3) . . ?
C1 C6 C7 113.6(2) . . ?
C13 C12 C11 121.0(2) . . ?
C12 C11 C16 118.1(2) . . ?
C12 C11 C10 118.4(2) . . ?
C16 C11 C10 123.5(2) . . ?
C2 C1 C6 120.2(2) . . ?
C2 C1 P1 129.9(2) . . ?
C6 C1 P1 108.6(2) . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 P1 122.98(19) . . ?
C11 C16 P1 116.05(19) . . ?
C4 C5 C6 120.3(3) . . ?
C9 C10 C11 127.1(3) . . ?
C10 C9 C8 118.7(3) . . ?
C12 C13 C14 120.5(2) . . ?
C3 C2 C1 119.6(3) . . ?
C8 C7 C6 112.9(3) . . ?
C3 C4 C5 120.2(3) . . ?
C7 C8 C9 130.0(3) . . ?
C7 C8 P1 111.2(2) . . ?
C9 C8 P1 118.7(2) . . ?
C2 C3 C4 120.6(3) . . ?

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
C16 C15 C14 C13 -1.6(4) . . . . ?
C13 C12 C11 C16 0.0(4) . . . . ?
C13 C12 C11 C10 -179.2(3) . . . . ?
C5 C6 C1 C2 0.5(4) . . . . ?
C7 C6 C1 C2 179.3(2) . . . . ?
C5 C6 C1 P1 168.8(2) . . . . ?
C7 C6 C1 P1 -12.3(3) . . . . ?
C8 P1 C1 C2 -177.9(2) . . . . ?
C16 P1 C1 C2 -76.5(3) . . . . ?
C8 P1 C1 C6 15.17(18) . . . . ?
C16 P1 C1 C6 116.60(18) . . . . ?
C14 C15 C16 C11 2.2(4) . . . . ?
C14 C15 C16 P1 171.8(2) . . . . ?
C12 C11 C16 C15 -1.4(4) . . . . ?
C10 C11 C16 C15 177.8(3) . . . . ?
C12 C11 C16 P1 -171.7(2) . . . . ?
C10 C11 C16 P1 7.6(3) . . . . ?
C8 P1 C16 C15 159.1(2) . . . . ?
C1 P1 C16 C15 63.3(3) . . . . ?
C8 P1 C16 C11 -31.0(2) . . . . ?
C1 P1 C16 C11 -126.80(19) . . . . ?
C1 C6 C5 C4 1.4(4) . . . . ?
C7 C6 C5 C4 -177.3(3) . . . . ?
C12 C11 C10 C9 -166.8(3) . . . . ?
C16 C11 C10 C9 14.0(4) . . . . ?
C11 C10 C9 C8 -0.4(5) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C15 C14 C13 C12 0.3(4) . . . . ?
C6 C1 C2 C3 -2.7(4) . . . . ?
P1 C1 C2 C3 -168.3(2) . . . . ?
C5 C6 C7 C8 -180.0(3) . . . . ?
C1 C6 C7 C8 1.3(3) . . . . ?
C6 C5 C4 C3 -1.0(4) . . . . ?
C6 C7 C8 C9 -165.2(3) . . . . ?
C6 C7 C8 P1 10.6(3) . . . . ?
C10 C9 C8 C7 142.8(3) . . . . ?
C10 C9 C8 P1 -32.7(4) . . . . ?
C1 P1 C8 C7 -15.0(2) . . . . ?
C16 P1 C8 C7 -131.5(2) . . . . ?
C1 P1 C8 C9 161.4(2) . . . . ?
C16 P1 C8 C9 44.9(2) . . . . ?
C1 C2 C3 C4 3.2(4) . . . . ?
C5 C4 C3 C2 -1.4(5) . . . . ?

#==============================================================================

####################################################################### 
# 
# 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_compound1b
_database_code_depnum_ccdc_archive 'CCDC 1886030'
loop_
_audit_author_name
_audit_author_address
'Akihiro Tsurusaki'
;Osaka Prefecture University
Japan
;
_audit_update_record             
;
2018-12-19 deposited with the CCDC.	2019-03-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7


#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        dibenzo[b,e]phosphindolizine-P-sulfide
_chemical_name_common            ?
_chemical_melting_point          '180 \%C, decomp.'
_chemical_formula_moiety         'C16 H11 P S'
_chemical_formula_sum            'C16 H11 P S'
_chemical_formula_weight         266.28

#==============================================================================

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.099(2)
_cell_length_b                   12.750(4)
_cell_length_c                   27.638(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2501.6(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    6528
_cell_measurement_theta_min      3.1955
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.362
_shelx_estimated_absorpt_T_min   0.934
_shelx_estimated_absorpt_T_max   0.958
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?

#==============================================================================

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_detector       CCD
_diffrn_measurement_device_type  'Saturn724+ (4x4 bin mode)'
_diffrn_measurement_method       dtprofit.ref
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            23615
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.195
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994

#==============================================================================
# REFINEMENT DATA

_reflns_number_total             2849
_reflns_number_gt                2747
_reflns_threshold_expression     'I > 2σ(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.
;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+1.6094P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2849
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0899
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.057

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'

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SIR2014 (Giacovazzo et al., 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  
'SHELXL-2014/7 and Yadokari-XG 2009 (Kabuto et al., 2009)'

#==============================================================================

# 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 0.77774(5) 0.12991(3) 0.88228(2) 0.01636(11) Uani 1 1 d . . . . .
S1 S 0.51705(5) 0.09779(3) 0.86480(2) 0.02130(11) Uani 1 1 d . . . . .
C1 C 0.8186(2) 0.13396(11) 0.94689(5) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.86689(19) 0.23761(11) 0.95947(5) 0.0189(3) Uani 1 1 d . . . . .
C14 C 1.1022(2) -0.09997(12) 0.82218(6) 0.0236(3) Uani 1 1 d . . . . .
H14 H 1.1323 -0.1714 0.8281 0.028 Uiso 1 1 calc R U . . .
C5 C 0.8822(2) 0.26463(11) 1.00815(5) 0.0209(3) Uani 1 1 d . . . . .
H5 H 0.9140 0.3342 1.0173 0.025 Uiso 1 1 calc R U . . .
C2 C 0.7852(2) 0.05865(12) 0.98184(5) 0.0213(3) Uani 1 1 d . . . . .
H2 H 0.7505 -0.0107 0.9729 0.026 Uiso 1 1 calc R U . . .
C12 C 1.1303(2) 0.05494(12) 0.77287(5) 0.0223(3) Uani 1 1 d . . . . .
H12 H 1.1775 0.0878 0.7445 0.027 Uiso 1 1 calc R U . . .
C8 C 0.8638(2) 0.26174(11) 0.87442(5) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.9461(2) 0.05998(11) 0.84600(5) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.8971(2) 0.30703(11) 0.91776(5) 0.0205(3) Uani 1 1 d . . . . .
H7 H 0.9367 0.3778 0.9210 0.025 Uiso 1 1 calc R U . . .
C11 C 1.0180(2) 0.11278(11) 0.80493(5) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.8502(2) 0.18838(12) 1.04323(5) 0.0231(3) Uani 1 1 d . . . . .
H4 H 0.8607 0.2065 1.0765 0.028 Uiso 1 1 calc R U . . .
C13 C 1.1739(2) -0.04926(13) 0.78177(5) 0.0242(3) Uani 1 1 d . . . . .
H13 H 1.2534 -0.0862 0.7600 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8034(2) 0.08633(12) 1.03057(5) 0.0231(3) Uani 1 1 d . . . . .
H3 H 0.7836 0.0352 1.0551 0.028 Uiso 1 1 calc R U . . .
C10 C 0.9840(2) 0.22428(12) 0.79452(5) 0.0229(3) Uani 1 1 d . . . . .
H10 H 1.0119 0.2483 0.7628 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9860(2) -0.04531(12) 0.85388(5) 0.0204(3) Uani 1 1 d . . . . .
H15 H 0.9335 -0.0802 0.8811 0.025 Uiso 1 1 calc R U . . .
C9 C 0.9167(2) 0.29519(12) 0.82615(5) 0.0229(3) Uani 1 1 d . . . . .
H9 H 0.9039 0.3666 0.8169 0.027 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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.
;

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 C16 1.7969(15) . ?
P1 C8 1.8016(16) . ?
P1 C1 1.8098(15) . ?
P1 S1 1.9559(8) . ?
C1 C2 1.383(2) . ?
C1 C6 1.409(2) . ?
C6 C5 1.393(2) . ?
C6 C7 1.469(2) . ?
C14 C13 1.387(2) . ?
C14 C15 1.391(2) . ?
C5 C4 1.392(2) . ?
C2 C3 1.398(2) . ?
C12 C13 1.386(2) . ?
C12 C11 1.402(2) . ?
C8 C7 1.351(2) . ?
C8 C9 1.450(2) . ?
C16 C15 1.389(2) . ?
C16 C11 1.4149(19) . ?
C11 C10 1.470(2) . ?
C4 C3 1.388(2) . ?
C10 C9 1.345(2) . ?

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
C16 P1 C8 99.80(7) . . ?
C16 P1 C1 117.27(7) . . ?
C8 P1 C1 92.18(7) . . ?
C16 P1 S1 112.80(5) . . ?
C8 P1 S1 119.11(5) . . ?
C1 P1 S1 113.66(5) . . ?
C2 C1 C6 121.38(13) . . ?
C2 C1 P1 129.96(11) . . ?
C6 C1 P1 108.02(10) . . ?
C5 C6 C1 119.29(13) . . ?
C5 C6 C7 126.70(14) . . ?
C1 C6 C7 114.01(12) . . ?
C13 C14 C15 119.42(14) . . ?
C4 C5 C6 119.17(14) . . ?
C1 C2 C3 118.82(14) . . ?
C13 C12 C11 121.28(13) . . ?
C7 C8 C9 130.16(14) . . ?
C7 C8 P1 110.57(11) . . ?
C9 C8 P1 118.24(11) . . ?
C15 C16 C11 120.80(13) . . ?
C15 C16 P1 121.85(11) . . ?
C11 C16 P1 116.83(11) . . ?
C8 C7 C6 114.39(13) . . ?
C12 C11 C16 117.51(13) . . ?
C12 C11 C10 118.57(13) . . ?
C16 C11 C10 123.91(13) . . ?
C3 C4 C5 121.24(13) . . ?
C12 C13 C14 120.52(14) . . ?
C4 C3 C2 120.09(14) . . ?
C9 C10 C11 125.51(14) . . ?
C16 C15 C14 120.43(14) . . ?
C10 C9 C8 119.47(14) . . ?

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
C16 P1 C1 C2 -78.58(16) . . . . ?
C8 P1 C1 C2 179.23(15) . . . . ?
S1 P1 C1 C2 55.99(15) . . . . ?
C16 P1 C1 C6 110.77(11) . . . . ?
C8 P1 C1 C6 8.58(11) . . . . ?
S1 P1 C1 C6 -114.67(9) . . . . ?
C2 C1 C6 C5 0.3(2) . . . . ?
P1 C1 C6 C5 171.92(11) . . . . ?
C2 C1 C6 C7 -179.93(13) . . . . ?
P1 C1 C6 C7 -8.32(15) . . . . ?
C1 C6 C5 C4 0.3(2) . . . . ?
C7 C6 C5 C4 -179.42(14) . . . . ?
C6 C1 C2 C3 -1.1(2) . . . . ?
P1 C1 C2 C3 -170.71(12) . . . . ?
C16 P1 C8 C7 -125.14(11) . . . . ?
C1 P1 C8 C7 -6.99(12) . . . . ?
S1 P1 C8 C7 111.75(10) . . . . ?
C16 P1 C8 C9 44.42(13) . . . . ?
C1 P1 C8 C9 162.57(12) . . . . ?
S1 P1 C8 C9 -78.69(12) . . . . ?
C8 P1 C16 C15 155.48(12) . . . . ?
C1 P1 C16 C15 57.87(14) . . . . ?
S1 P1 C16 C15 -77.06(12) . . . . ?
C8 P1 C16 C11 -32.73(12) . . . . ?
C1 P1 C16 C11 -130.33(11) . . . . ?
S1 P1 C16 C11 94.73(11) . . . . ?
C9 C8 C7 C6 -164.48(15) . . . . ?
P1 C8 C7 C6 3.46(16) . . . . ?
C5 C6 C7 C8 -176.88(14) . . . . ?
C1 C6 C7 C8 3.37(19) . . . . ?
C13 C12 C11 C16 -1.8(2) . . . . ?
C13 C12 C11 C10 177.30(14) . . . . ?
C15 C16 C11 C12 -0.1(2) . . . . ?
P1 C16 C11 C12 -171.97(11) . . . . ?
C15 C16 C11 C10 -179.16(14) . . . . ?
P1 C16 C11 C10 8.96(19) . . . . ?
C6 C5 C4 C3 -0.1(2) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C15 C14 C13 C12 0.0(2) . . . . ?
C5 C4 C3 C2 -0.8(2) . . . . ?
C1 C2 C3 C4 1.4(2) . . . . ?
C12 C11 C10 C9 -164.40(15) . . . . ?
C16 C11 C10 C9 14.7(2) . . . . ?
C11 C16 C15 C14 1.9(2) . . . . ?
P1 C16 C15 C14 173.39(11) . . . . ?
C13 C14 C15 C16 -1.9(2) . . . . ?
C11 C10 C9 C8 -2.8(2) . . . . ?
C7 C8 C9 C10 136.71(17) . . . . ?
P1 C8 C9 C10 -30.46(19) . . . . ?

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