# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_exp_18397
_database_code_depnum_ccdc_archive 'CCDC 1877298'
_audit_update_record             
;
2018-11-06 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        
'((5-chloro-1H-indol-3-yl)(4-chlorophenyl)methyl)diphenylphosphine oxide'
_chemical_formula_moiety         'C27 H20 Cl2 N O P'
_chemical_formula_sum            'C27 H20 Cl2 N O P'
_chemical_formula_weight         476.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.5940(2)
_cell_length_b                   11.0586(3)
_cell_length_c                   21.6374(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.293(2)
_cell_angle_gamma                90
_cell_volume                     2291.86(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3165
_cell_measurement_temperature    173
_cell_measurement_theta_max      62.1950
_cell_measurement_theta_min      4.0780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7551
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         62.043
_diffrn_reflns_theta_min         4.093
_diffrn_ambient_temperature      173
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1903
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     20.00 103.00   1.00    1.20    --   32.31  57.00 -30.00   83
  2  ω     91.00 164.00   1.00    4.79    --   94.50  64.00  90.00   73
  3  ω     67.00 117.00   1.00    4.79    --   94.50 -50.00 -60.00   50
  4  ω     79.00 121.00   1.00    4.79    --   94.50 -92.00   0.00   42
  5  ω     70.00  96.00   1.00    4.79    --   94.50 -92.00 -90.00   26
  6  ω     64.00  90.00   1.00    4.79    --   94.50 -93.00 -20.90   26
  7  ω     37.00 132.00   1.00    4.79    --   94.50 -92.00 -60.00   95
  8  ω     99.00 167.00   1.00    4.79    --   94.50  38.00-120.00   68
  9  ω     69.00 156.00   1.00    4.79    --   94.50  50.00  30.00   87
 10  ω     52.00 103.00   1.00    1.20    --   32.31  57.00-180.00   51
 11  ω     30.00  62.00   1.00    4.79    --   94.50 -50.00 -60.00   32
 12  ω     23.00  63.00   1.00    4.79    --   94.50 -92.00 -90.00   40
 13  ω     32.00  85.00   1.00    4.79    --   94.50 -50.00  30.00   53
 14  ω    -14.00  73.00   1.00    1.20    --   32.31 -99.00 120.00   87
 15  ω   -114.00 -58.00   1.00    1.20    --  -32.31 178.00 -90.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0532065000
_diffrn_orient_matrix_UB_12      0.1273225000
_diffrn_orient_matrix_UB_13      -0.0180677000
_diffrn_orient_matrix_UB_21      0.1313178000
_diffrn_orient_matrix_UB_22      0.0560234000
_diffrn_orient_matrix_UB_23      0.0328130000
_diffrn_orient_matrix_UB_31      0.0760032000
_diffrn_orient_matrix_UB_32      -0.0076933000
_diffrn_orient_matrix_UB_33      -0.0607114000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3186
_reflns_number_total             3576
_reflns_odcompleteness_completeness 99.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     61.08
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         3576
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0484
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0859P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1323
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C15(H15), C23(H23), C1(H1A), C27(H27), C11(H11), C14(H14), C4(H4),
 C12(H12), C25(H25), C26(H26), C24(H24), C17(H17), C19(H19), C7(H7), C18(H18),
 C21(H21), C20(H20), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.69217(5) 0.43307(5) 0.35760(2) 0.02182(19) Uani 1 1 d . . . . .
Cl2 Cl 0.17663(6) 0.11455(6) 0.20068(3) 0.0408(2) Uani 1 1 d . . . . .
Cl1 Cl 0.87870(10) -0.11457(7) 0.52970(3) 0.0608(3) Uani 1 1 d . . . . .
O1 O 0.58906(16) 0.52981(15) 0.37016(6) 0.0271(4) Uani 1 1 d . . . . .
N1 N 0.5186(2) 0.30870(19) 0.54145(9) 0.0308(5) Uani 1 1 d . . . . .
H1 H 0.4719 0.3418 0.5697 0.037 Uiso 1 1 calc R . . . .
C2 C 0.6083(2) 0.2761(2) 0.44921(9) 0.0236(5) Uani 1 1 d . . . . .
C3 C 0.6581(2) 0.1839(2) 0.49100(10) 0.0268(5) Uani 1 1 d . . . . .
C10 C 0.5201(2) 0.2377(2) 0.33745(9) 0.0233(5) Uani 1 1 d . . . . .
C15 C 0.5418(2) 0.1441(2) 0.29640(10) 0.0292(5) Uani 1 1 d . . . . .
H15 H 0.6286 0.1065 0.2971 0.035 Uiso 1 1 calc R . . . .
C9 C 0.6388(2) 0.2815(2) 0.38165(9) 0.0234(5) Uani 1 1 d . . . . .
H9 H 0.7182 0.2276 0.3762 0.028 Uiso 1 1 calc R . . . .
C23 C 0.6214(3) 0.4701(2) 0.23345(11) 0.0314(5) Uani 1 1 d . . . . .
H23 H 0.5531 0.5215 0.2473 0.038 Uiso 1 1 calc R . . . .
C1 C 0.5237(2) 0.3488(2) 0.48176(10) 0.0271(5) Uani 1 1 d . . . . .
H1A H 0.4762 0.4161 0.4656 0.033 Uiso 1 1 calc R . . . .
C22 C 0.7143(2) 0.4142(2) 0.27553(10) 0.0255(5) Uani 1 1 d . . . . .
C27 C 0.8154(3) 0.3370(2) 0.25448(11) 0.0310(5) Uani 1 1 d . . . . .
H27 H 0.8784 0.2995 0.2826 0.037 Uiso 1 1 calc R . . . .
C11 C 0.3898(2) 0.2930(2) 0.33556(11) 0.0314(5) Uani 1 1 d . . . . .
H11 H 0.3732 0.3556 0.3629 0.038 Uiso 1 1 calc R . . . .
C8 C 0.6002(2) 0.2068(2) 0.54880(10) 0.0303(5) Uani 1 1 d . . . . .
C14 C 0.4365(3) 0.1056(2) 0.25426(11) 0.0331(6) Uani 1 1 d . . . . .
H14 H 0.4518 0.0423 0.2272 0.040 Uiso 1 1 calc R . . . .
C16 C 0.8633(2) 0.4669(2) 0.39234(9) 0.0254(5) Uani 1 1 d . . . . .
C4 C 0.7453(3) 0.0839(2) 0.48528(11) 0.0335(6) Uani 1 1 d . . . . .
H4 H 0.7850 0.0668 0.4481 0.040 Uiso 1 1 calc R . . . .
C13 C 0.3094(2) 0.1627(2) 0.25326(10) 0.0299(5) Uani 1 1 d . . . . .
C12 C 0.2842(3) 0.2557(2) 0.29327(11) 0.0344(6) Uani 1 1 d . . . . .
H12 H 0.1974 0.2933 0.2920 0.041 Uiso 1 1 calc R . . . .
C25 C 0.7311(3) 0.3731(3) 0.14967(11) 0.0399(6) Uani 1 1 d . . . . .
H25 H 0.7378 0.3603 0.1075 0.048 Uiso 1 1 calc R . . . .
C26 C 0.8228(3) 0.3155(2) 0.19162(12) 0.0382(6) Uani 1 1 d . . . . .
H26 H 0.8893 0.2623 0.1777 0.046 Uiso 1 1 calc R . . . .
C24 C 0.6302(3) 0.4493(3) 0.17005(11) 0.0390(6) Uani 1 1 d . . . . .
H24 H 0.5678 0.4869 0.1417 0.047 Uiso 1 1 calc R . . . .
C17 C 0.9661(3) 0.3817(2) 0.40713(12) 0.0363(6) Uani 1 1 d . . . . .
H17 H 0.9469 0.2997 0.4022 0.044 Uiso 1 1 calc R . . . .
C5 C 0.7705(3) 0.0119(3) 0.53610(12) 0.0412(6) Uani 1 1 d . . . . .
C19 C 1.1277(3) 0.5398(3) 0.43617(12) 0.0379(6) Uani 1 1 d . . . . .
H19 H 1.2164 0.5640 0.4507 0.046 Uiso 1 1 calc R . . . .
C7 C 0.6280(3) 0.1322(3) 0.59966(11) 0.0416(6) Uani 1 1 d . . . . .
H7 H 0.5899 0.1484 0.6373 0.050 Uiso 1 1 calc R . . . .
C18 C 1.0979(3) 0.4193(3) 0.42938(13) 0.0415(6) Uani 1 1 d . . . . .
H18 H 1.1664 0.3622 0.4397 0.050 Uiso 1 1 calc R . . . .
C21 C 0.8951(3) 0.5875(3) 0.40031(13) 0.0421(6) Uani 1 1 d . . . . .
H21 H 0.8266 0.6454 0.3912 0.051 Uiso 1 1 calc R . . . .
C20 C 1.0276(3) 0.6243(3) 0.42168(14) 0.0476(7) Uani 1 1 d . . . . .
H20 H 1.0480 0.7062 0.4261 0.057 Uiso 1 1 calc R . . . .
C6 C 0.7131(3) 0.0341(3) 0.59291(12) 0.0464(7) Uani 1 1 d . . . . .
H6 H 0.7327 -0.0177 0.6262 0.056 Uiso 1 1 calc R . . . .


_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 1.4926(16) . ?
P1 C9 1.837(2) . ?
P1 C22 1.813(2) . ?
P1 C16 1.805(2) . ?
Cl2 C13 1.741(2) . ?
Cl1 C5 1.752(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.369(3) . ?
N1 C8 1.376(3) . ?
C2 C3 1.427(3) . ?
C2 C9 1.508(3) . ?
C2 C1 1.366(3) . ?
C3 C8 1.420(3) . ?
C3 C4 1.396(4) . ?
C10 C15 1.387(3) . ?
C10 C9 1.524(3) . ?
C10 C11 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C14 1.389(3) . ?
C9 H9 0.9800 . ?
C23 H23 0.9300 . ?
C23 C22 1.383(3) . ?
C23 C24 1.398(3) . ?
C1 H1A 0.9300 . ?
C22 C27 1.389(3) . ?
C27 H27 0.9300 . ?
C27 C26 1.387(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.388(3) . ?
C8 C7 1.389(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.372(4) . ?
C16 C17 1.388(4) . ?
C16 C21 1.377(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.368(4) . ?
C13 C12 1.375(4) . ?
C12 H12 0.9300 . ?
C25 H25 0.9300 . ?
C25 C26 1.383(4) . ?
C25 C24 1.376(4) . ?
C26 H26 0.9300 . ?
C24 H24 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.391(4) . ?
C5 C6 1.397(4) . ?
C19 H19 0.9300 . ?
C19 C18 1.368(4) . ?
C19 C20 1.364(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.370(4) . ?
C18 H18 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.388(4) . ?
C20 H20 0.9300 . ?
C6 H6 0.9300 . ?

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 C9 113.84(10) . . ?
O1 P1 C22 112.16(10) . . ?
O1 P1 C16 111.83(10) . . ?
C22 P1 C9 102.87(10) . . ?
C16 P1 C9 109.45(10) . . ?
C16 P1 C22 106.07(10) . . ?
C1 N1 H1 125.6 . . ?
C1 N1 C8 108.86(19) . . ?
C8 N1 H1 125.6 . . ?
C3 C2 C9 124.44(19) . . ?
C1 C2 C3 106.32(19) . . ?
C1 C2 C9 129.1(2) . . ?
C8 C3 C2 107.3(2) . . ?
C4 C3 C2 133.7(2) . . ?
C4 C3 C8 119.1(2) . . ?
C15 C10 C9 120.3(2) . . ?
C15 C10 C11 118.5(2) . . ?
C11 C10 C9 121.2(2) . . ?
C10 C15 H15 119.4 . . ?
C10 C15 C14 121.3(2) . . ?
C14 C15 H15 119.4 . . ?
P1 C9 H9 106.8 . . ?
C2 C9 P1 112.51(15) . . ?
C2 C9 C10 114.62(17) . . ?
C2 C9 H9 106.8 . . ?
C10 C9 P1 108.81(14) . . ?
C10 C9 H9 106.8 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
N1 C1 H1A 124.7 . . ?
C2 C1 N1 110.5(2) . . ?
C2 C1 H1A 124.7 . . ?
C23 C22 P1 119.08(18) . . ?
C23 C22 C27 119.7(2) . . ?
C27 C22 P1 121.04(17) . . ?
C22 C27 H27 119.9 . . ?
C26 C27 C22 120.2(2) . . ?
C26 C27 H27 119.9 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.7 . . ?
N1 C8 C3 107.1(2) . . ?
N1 C8 C7 131.3(2) . . ?
C7 C8 C3 121.6(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14 120.6 . . ?
C17 C16 P1 124.91(19) . . ?
C21 C16 P1 116.30(19) . . ?
C21 C16 C17 118.6(2) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4 121.0 . . ?
C14 C13 Cl2 119.06(19) . . ?
C14 C13 C12 121.5(2) . . ?
C12 C13 Cl2 119.47(19) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C26 C25 H25 119.8 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.3(2) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 C27 119.9(2) . . ?
C25 C26 H26 120.1 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.1 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.8(2) . . ?
C18 C17 H17 120.1 . . ?
C4 C5 Cl1 118.6(2) . . ?
C4 C5 C6 123.0(2) . . ?
C6 C5 Cl1 118.4(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C18 120.2(2) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 C8 118.3(2) . . ?
C6 C7 H7 120.8 . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C16 C21 H21 119.4 . . ?
C16 C21 C20 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C19 C20 C21 119.7(3) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.808
_oxdiff_exptl_absorpt_empirical_full_min 0.541
####################################################################### 
# 
# 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_exp_2608
_database_code_depnum_ccdc_archive 'CCDC 1877299'
_audit_update_record             
;
2018-11-06 deposited with the CCDC.
2019-01-21 downloaded from the CCDC.
;
_audit_creation_date             2018-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        
'(5-chloro-3-(1-phenylbutyl)-1H-indol-2-yl)diphenylphosphine oxide'
_chemical_formula_moiety         'C30 H27 Cl N O P'
_chemical_formula_sum            'C30 H27 Cl N O P'
_chemical_formula_weight         483.98
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.30360 0.43703 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   8.60810(10)
_cell_length_b                   16.0745(2)
_cell_length_c                   18.0657(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.4650(10)
_cell_angle_gamma                90
_cell_volume                     2465.74(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9128
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.9260
_cell_measurement_theta_min      2.7540
_exptl_absorpt_coefficient_mu    2.160
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31851
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.21a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3036
_exptl_crystal_description       plate
_exptl_crystal_F_000             1021.2236
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0393
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16972
_diffrn_reflns_theta_full        77.7979
_diffrn_reflns_theta_max         77.80
_diffrn_reflns_theta_min         3.70
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.9591
_diffrn_measured_fraction_theta_max 0.9591
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      7.00  62.00   0.50    0.05    --   46.75 -65.00  29.00  110
  2  ω     38.00 128.00   0.50    0.11    --  109.54 -65.00  29.00  180
  3  ω     95.00 174.00   0.50    0.11    --  109.54  15.00 120.00  158
  4  ω     92.00 118.00   0.50    0.11    --  109.54  65.00 165.00   52
  5  ω     49.00  74.00   0.50    0.05    --   46.75  65.00 165.00   50
  6  ω     37.00 104.00   0.50    0.11    --  109.54 -94.00 -60.00  134
  7  ω     73.00 106.00   0.50    0.11    --  109.54 -94.00-120.00   66
  8  ω     43.00  87.00   0.50    0.11    --  109.54 -94.00-180.00   88
  9  ω     38.00 108.00   0.50    0.11    --  109.54 -94.00 -90.00  140
 10  ω     39.00 104.00   0.50    0.11    --  109.54-125.00  30.00  130
 11  ω     96.00 166.00   0.50    0.11    --  109.54  45.00-150.00  140
 12  ω    -45.00 -20.00   0.50    0.11    --  -88.50  65.00 165.00   50
 13  ω    -66.00  23.00   0.50    0.05    --  -46.75  65.00 165.00  178
 14  ω    -90.00 -24.00   0.50    0.11    --  -88.50 125.00 -60.00  132
 15  ω   -112.00 -28.00   0.50    0.05    --  -46.75 -65.00  29.00  168
 16  ω   -119.00 -74.00   0.50    0.05    --  -46.75-125.00 150.00   90
 17  ω   -154.00 -80.00   0.50    0.11    --  -88.50 -65.00  29.00  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008014000
_diffrn_orient_matrix_UB_12      0.0089075000
_diffrn_orient_matrix_UB_13      -0.0849730000
_diffrn_orient_matrix_UB_21      -0.1209534000
_diffrn_orient_matrix_UB_22      -0.0711146000
_diffrn_orient_matrix_UB_23      -0.0151800000
_diffrn_orient_matrix_UB_31      -0.1351994000
_diffrn_orient_matrix_UB_32      0.0636354000
_diffrn_orient_matrix_UB_33      -0.0050217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                4766
_reflns_number_total             5042
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.46
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.21a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.7546
_refine_diff_density_min         -0.6065
_refine_diff_density_rms         0.1263
_refine_ls_d_res_high            0.7887
_refine_ls_d_res_low             11.9358
_refine_ls_goodness_of_fit_ref   1.0309
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5042
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0817
_refine_ls_R_factor_gt           0.0738
_refine_ls_restrained_S_all      1.0309
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0858P)²+9.3901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1859
_refine_ls_wR_factor_ref         0.2001
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10a,H10b), C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C24(H24), C4(H4), C26(H26), C20(H20), C7(H7), C23(H23), C6(H6),
 C22(H22), C21(H21), C30(H30), C28(H28), C27(H27), C18(H18), C29(H29), C14(H14),
  C17(H17), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
P1 P 0.84990(10) 0.34828(5) 0.51682(4) 0.0179(2) Uani 1.000000 .
Cl1 Cl 0.59587(13) 0.45540(5) 0.07922(5) 0.0337(3) Uani 1.000000 .
O1 O 0.9568(3) 0.41291(14) 0.55677(13) 0.0231(5) Uani 1.000000 .
N1 N 0.8710(3) 0.44717(16) 0.39623(15) 0.0203(6) Uani 1.000000 .
H1 H 0.9340(3) 0.47972(16) 0.42464(15) 0.0244(7) Uiso 1.000000 R
C8 C 0.8187(4) 0.45898(19) 0.32181(18) 0.0192(6) Uani 1.000000 .
C25 C 0.9336(4) 0.2454(2) 0.52412(18) 0.0205(7) Uani 1.000000 .
C19 C 0.6636(4) 0.34578(19) 0.54940(17) 0.0199(6) Uani 1.000000 .
C3 C 0.7183(4) 0.39142(19) 0.29535(18) 0.0189(6) Uani 1.000000 .
C2 C 0.7123(4) 0.33799(19) 0.35796(18) 0.0192(6) Uani 1.000000 .
C24 C 0.5719(4) 0.2743(2) 0.55308(18) 0.0230(7) Uani 1.000000 .
H24 H 0.6103(4) 0.2225(2) 0.54193(18) 0.0277(8) Uiso 1.000000 R
C4 C 0.6479(4) 0.3895(2) 0.21875(18) 0.0221(7) Uani 1.000000 .
H4 H 0.5822(4) 0.3461(2) 0.19938(18) 0.0266(8) Uiso 1.000000 R
C1 C 0.8070(4) 0.37471(19) 0.41900(18) 0.0186(6) Uani 1.000000 .
C9 C 0.6218(4) 0.25752(19) 0.35767(18) 0.0208(7) Uani 1.000000 .
H9 H 0.6331(4) 0.23932(19) 0.41006(18) 0.0249(8) Uiso 1.000000 R
C26 C 0.9332(4) 0.1975(2) 0.5884(2) 0.0270(7) Uani 1.000000 .
H26 H 0.8799(4) 0.2164(2) 0.6259(2) 0.0324(9) Uiso 1.000000 R
C13 C 0.4466(4) 0.2733(2) 0.3316(2) 0.0239(7) Uani 1.000000 .
C20 C 0.6040(5) 0.4229(2) 0.5680(2) 0.0276(8) Uani 1.000000 .
H20 H 0.6645(5) 0.4707(2) 0.5668(2) 0.0331(9) Uiso 1.000000 R
C10 C 0.6918(4) 0.1883(2) 0.3151(2) 0.0262(7) Uani 1.000000 .
H10a H 0.6533(4) 0.1949(2) 0.2619(2) 0.0314(9) Uiso 1.000000 R
H10b H 0.8053(4) 0.1948(2) 0.3228(2) 0.0314(9) Uiso 1.000000 R
C7 C 0.8504(5) 0.5241(2) 0.2749(2) 0.0269(8) Uani 1.000000 .
H7 H 0.9168(5) 0.5678(2) 0.2931(2) 0.0322(9) Uiso 1.000000 R
C5 C 0.6806(4) 0.4543(2) 0.17427(18) 0.0248(7) Uani 1.000000 .
C23 C 0.4239(4) 0.2808(2) 0.5733(2) 0.0284(8) Uani 1.000000 .
H23 H 0.3636(4) 0.2333(2) 0.5761(2) 0.0341(9) Uiso 1.000000 R
C6 C 0.7796(5) 0.5211(2) 0.2009(2) 0.0280(8) Uani 1.000000 .
H6 H 0.7974(5) 0.5635(2) 0.1683(2) 0.0337(9) Uiso 1.000000 R
C11 C 0.6540(5) 0.1019(2) 0.3379(2) 0.0320(8) Uani 1.000000 .
H11a H 0.6979(5) 0.0936(2) 0.3903(2) 0.0384(10) Uiso 1.000000 R
H11b H 0.5406(5) 0.0956(2) 0.3325(2) 0.0384(10) Uiso 1.000000 R
C22 C 0.3651(5) 0.3579(3) 0.5895(2) 0.0330(8) Uani 1.000000 .
H22 H 0.2643(5) 0.3620(3) 0.6015(2) 0.0396(10) Uiso 1.000000 R
C21 C 0.4563(5) 0.4285(2) 0.5880(2) 0.0319(8) Uani 1.000000 .
H21 H 0.4180(5) 0.4798(2) 0.6004(2) 0.0383(10) Uiso 1.000000 R
C30 C 1.0185(5) 0.2169(2) 0.4696(2) 0.0338(9) Uani 1.000000 .
H30 H 1.0220(5) 0.2487(2) 0.4269(2) 0.0406(10) Uiso 1.000000 R
C28 C 1.0927(5) 0.0942(2) 0.5418(2) 0.0340(9) Uani 1.000000 .
H28 H 1.1445(5) 0.0432(2) 0.5472(2) 0.0408(11) Uiso 1.000000 R
C27 C 1.0116(5) 0.1219(2) 0.5968(2) 0.0333(9) Uani 1.000000 .
H27 H 1.0095(5) 0.0899(2) 0.6396(2) 0.0400(10) Uiso 1.000000 R
C18 C 0.3735(5) 0.3355(2) 0.3695(2) 0.0326(8) Uani 1.000000 .
H18 H 0.4330(5) 0.3639(2) 0.4092(2) 0.0391(10) Uiso 1.000000 R
C29 C 1.0971(6) 0.1420(3) 0.4788(2) 0.0424(10) Uani 1.000000 .
H29 H 1.1535(6) 0.1236(3) 0.4422(2) 0.0509(13) Uiso 1.000000 R
C14 C 0.3572(5) 0.2327(3) 0.2749(3) 0.0386(9) Uani 1.000000 .
H14 H 0.4020(5) 0.1910(3) 0.2496(3) 0.0463(11) Uiso 1.000000 R
C12 C 0.7201(6) 0.0348(2) 0.2902(3) 0.0551(15) Uani 1.000000 .
H12a H 0.658(3) 0.0333(18) 0.2410(8) 0.083(2) Uiso 1.000000 GR
H12b H 0.8272(18) 0.0480(14) 0.286(2) 0.083(2) Uiso 1.000000 GR
H12c H 0.716(5) -0.0185(5) 0.3138(13) 0.083(2) Uiso 1.000000 GR
C17 C 0.2193(6) 0.3547(3) 0.3493(3) 0.0430(10) Uani 1.000000 .
H17 H 0.1740(6) 0.3958(3) 0.3751(3) 0.0516(12) Uiso 1.000000 R
C16 C 0.1317(5) 0.3144(3) 0.2921(3) 0.0419(10) Uani 1.000000 .
H16 H 0.0259(5) 0.3279(3) 0.2780(3) 0.0502(12) Uiso 1.000000 R
C15 C 0.1994(5) 0.2523(3) 0.2536(3) 0.0442(11) Uani 1.000000 .
H15 H 0.1389(5) 0.2242(3) 0.2139(3) 0.0530(13) Uiso 1.000000 R


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 1.493(2) . ?
P1 C25 1.800(3) . ?
P1 C19 1.797(4) . ?
P1 C1 1.796(3) . ?
Cl1 C5 1.752(3) . ?
N1 H1 0.8600 . ?
N1 C8 1.359(4) . ?
N1 C1 1.380(4) . ?
C8 C3 1.421(4) . ?
C8 C7 1.402(4) . ?
C25 C26 1.393(5) . ?
C25 C30 1.396(5) . ?
C19 C24 1.402(5) . ?
C19 C20 1.404(5) . ?
C3 C2 1.428(4) . ?
C3 C4 1.417(4) . ?
C2 C1 1.391(5) . ?
C2 C9 1.509(4) . ?
C24 H24 0.9300 . ?
C24 C23 1.386(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(5) . ?
C9 H9 0.9800 . ?
C9 C13 1.525(5) . ?
C9 C10 1.532(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.386(5) . ?
C13 C18 1.417(5) . ?
C13 C14 1.344(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.381(6) . ?
C10 H10a 0.9700 . ?
C10 H10b 0.9700 . ?
C10 C11 1.499(5) . ?
C7 H7 0.9300 . ?
C7 C6 1.376(5) . ?
C5 C6 1.406(5) . ?
C23 H23 0.9300 . ?
C23 C22 1.387(6) . ?
C6 H6 0.9300 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?
C11 C12 1.545(6) . ?
C22 H22 0.9300 . ?
C22 C21 1.383(6) . ?
C21 H21 0.9300 . ?
C30 H30 0.9300 . ?
C30 C29 1.378(5) . ?
C28 H28 0.9300 . ?
C28 C27 1.379(6) . ?
C28 C29 1.380(6) . ?
C27 H27 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.353(6) . ?
C29 H29 0.9300 . ?
C14 H14 0.9300 . ?
C14 C15 1.386(6) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C17 H17 0.9300 . ?
C17 C16 1.342(7) . ?
C16 H16 0.9300 . ?
C16 C15 1.398(7) . ?
C15 H15 0.9300 . ?

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
C25 P1 O1 113.36(15) . . ?
C19 P1 O1 111.68(15) . . ?
C19 P1 C25 108.86(15) . . ?
C1 P1 O1 108.76(14) . . ?
C1 P1 C25 107.73(15) . . ?
C1 P1 C19 106.11(15) . . ?
C8 N1 H1 125.39(18) . . ?
C1 N1 H1 125.39(18) . . ?
C1 N1 C8 109.2(3) . . ?
C3 C8 N1 108.1(3) . . ?
C7 C8 N1 129.5(3) . . ?
C7 C8 C3 122.4(3) . . ?
C26 C25 P1 120.9(3) . . ?
C30 C25 P1 119.9(3) . . ?
C30 C25 C26 118.6(3) . . ?
C24 C19 P1 125.0(3) . . ?
C20 C19 P1 116.1(3) . . ?
C20 C19 C24 118.8(3) . . ?
C2 C3 C8 107.0(3) . . ?
C4 C3 C8 118.9(3) . . ?
C4 C3 C2 134.1(3) . . ?
C1 C2 C3 106.3(3) . . ?
C9 C2 C3 126.8(3) . . ?
C9 C2 C1 127.0(3) . . ?
H24 C24 C19 120.0(2) . . ?
C23 C24 C19 120.0(3) . . ?
C23 C24 H24 120.0(2) . . ?
H4 C4 C3 121.32(19) . . ?
C5 C4 C3 117.4(3) . . ?
C5 C4 H4 121.3(2) . . ?
N1 C1 P1 117.7(2) . . ?
C2 C1 P1 132.7(2) . . ?
C2 C1 N1 109.4(3) . . ?
H9 C9 C2 106.46(17) . . ?
C13 C9 C2 110.0(3) . . ?
C13 C9 H9 106.46(18) . . ?
C10 C9 C2 112.3(3) . . ?
C10 C9 H9 106.46(18) . . ?
C10 C9 C13 114.6(3) . . ?
H26 C26 C25 119.7(2) . . ?
C27 C26 C25 120.6(3) . . ?
C27 C26 H26 119.7(2) . . ?
C18 C13 C9 117.6(3) . . ?
C14 C13 C9 124.6(3) . . ?
C14 C13 C18 117.8(4) . . ?
H20 C20 C19 119.7(2) . . ?
C21 C20 C19 120.5(3) . . ?
C21 C20 H20 119.7(2) . . ?
H10a C10 C9 108.65(17) . . ?
H10b C10 C9 108.65(18) . . ?
H10b C10 H10a 107.6 . . ?
C11 C10 C9 114.5(3) . . ?
C11 C10 H10a 108.6(2) . . ?
C11 C10 H10b 108.6(2) . . ?
H7 C7 C8 121.2(2) . . ?
C6 C7 C8 117.5(3) . . ?
C6 C7 H7 121.2(2) . . ?
C4 C5 Cl1 119.3(3) . . ?
C6 C5 Cl1 117.3(3) . . ?
C6 C5 C4 123.4(3) . . ?
H23 C23 C24 119.8(2) . . ?
C22 C23 C24 120.4(3) . . ?
C22 C23 H23 119.8(2) . . ?
C5 C6 C7 120.4(3) . . ?
H6 C6 C7 119.8(2) . . ?
H6 C6 C5 119.8(2) . . ?
H11a C11 C10 109.2(2) . . ?
H11b C11 C10 109.2(2) . . ?
H11b C11 H11a 107.9 . . ?
C12 C11 C10 112.1(4) . . ?
C12 C11 H11a 109.2(2) . . ?
C12 C11 H11b 109.2(2) . . ?
H22 C22 C23 120.0(2) . . ?
C21 C22 C23 120.0(4) . . ?
C21 C22 H22 120.0(2) . . ?
C22 C21 C20 120.2(4) . . ?
H21 C21 C20 119.9(2) . . ?
H21 C21 C22 119.9(2) . . ?
H30 C30 C25 119.8(2) . . ?
C29 C30 C25 120.4(4) . . ?
C29 C30 H30 119.8(2) . . ?
C27 C28 H28 120.0(2) . . ?
C29 C28 H28 120.0(2) . . ?
C29 C28 C27 120.0(4) . . ?
C28 C27 C26 119.9(4) . . ?
H27 C27 C26 120.1(2) . . ?
H27 C27 C28 120.1(2) . . ?
H18 C18 C13 119.2(2) . . ?
C17 C18 C13 121.7(4) . . ?
C17 C18 H18 119.2(3) . . ?
C28 C29 C30 120.4(4) . . ?
H29 C29 C30 119.8(2) . . ?
H29 C29 C28 119.8(2) . . ?
H14 C14 C13 119.5(2) . . ?
C15 C14 C13 120.9(4) . . ?
C15 C14 H14 119.5(3) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H17 C17 C18 120.0(3) . . ?
C16 C17 C18 120.0(4) . . ?
C16 C17 H17 120.0(3) . . ?
H16 C16 C17 120.0(3) . . ?
C15 C16 C17 120.1(4) . . ?
C15 C16 H16 120.0(3) . . ?
C16 C15 C14 119.6(4) . . ?
H15 C15 C14 120.2(3) . . ?
H15 C15 C16 120.2(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.685
_oxdiff_exptl_absorpt_empirical_full_min 0.509
