# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_takeharu190208
_database_code_depnum_ccdc_archive 'CCDC 1990129'
loop_
_audit_author_name
_audit_author_address
'Hideaki Takano'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C26 H15 Cl'
_chemical_formula_moiety         'C26 H15 Cl'
_chemical_formula_weight         362.86
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   8.1345(2)
_cell_length_b                   11.3251(3)
_cell_length_c                   19.1576(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.945(7)
_cell_angle_gamma                90.0000
_cell_volume                     1762.54(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16576
_cell_measurement_theta_min      3.90
_cell_measurement_theta_max      68.17
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752.00
_exptl_absorpt_coefficient_mu    1.949
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.472
_exptl_absorpt_correction_T_max  0.907

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            18973
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         4.537
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3219
_reflns_number_gt                2455
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1529
_refine_ls_wR_factor_gt          0.1402
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3219
_refine_ls_number_parameters     244
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0701P)²+1.4811P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.38
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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
Cl1 Cl 0.65998(9) 0.27380(6) 0.74966(4) 0.0435(2) Uani 1 1 d . . . . .
C1 C 0.3734(3) 0.7992(2) 0.62030(13) 0.0306(6) Uani 1 1 d . . . . .
C2 C 0.4298(3) 0.5779(2) 0.62611(13) 0.0304(6) Uani 1 1 d . . . . .
C3 C 0.2524(3) 0.5389(2) 0.50174(13) 0.0321(6) Uani 1 1 d . . . . .
C4 C 0.3556(3) 0.6788(2) 0.58879(13) 0.0311(6) Uani 1 1 d . . . . .
C5 C 0.1778(3) 0.7329(3) 0.47588(14) 0.0351(6) Uani 1 1 d . . . . .
C6 C 0.3141(3) 0.4398(2) 0.53645(13) 0.0323(6) Uani 1 1 d . . . . .
C7 C 0.2712(3) 0.6580(2) 0.52683(13) 0.0324(6) Uani 1 1 d . . . . .
C8 C 0.5274(3) 0.5958(2) 0.68849(13) 0.0311(6) Uani 1 1 d . . . . .
H8 H 0.5431 0.6725 0.7049 0.037 Uiso 1 1 calc R U . . .
C9 C 0.4830(3) 0.3675(2) 0.64022(13) 0.0325(6) Uani 1 1 d . . . . .
H9 H 0.4691 0.2901 0.6248 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2751(4) 0.3295(3) 0.50455(14) 0.0366(7) Uani 1 1 d . . . . .
H10 H 0.3136 0.2599 0.5253 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5995(3) 0.5047(2) 0.72545(14) 0.0343(6) Uani 1 1 d . . . . .
H11 H 0.6636 0.5189 0.7662 0.041 Uiso 1 1 calc R U . . .
C12 C 0.2826(4) 0.8287(2) 0.67729(14) 0.0347(6) Uani 1 1 d . . . . .
H12 H 0.2088 0.7744 0.6943 0.042 Uiso 1 1 calc R U . . .
C13 C 0.1546(3) 0.5357(3) 0.43931(13) 0.0361(7) Uani 1 1 d . . . . .
C14 C 0.4101(3) 0.4599(2) 0.60124(13) 0.0310(6) Uani 1 1 d . . . . .
C15 C 0.3011(4) 0.9382(2) 0.70900(15) 0.0384(7) Uani 1 1 d . . . . .
H15 H 0.2399 0.9569 0.7472 0.046 Uiso 1 1 calc R U . . .
C16 C 0.1803(4) 0.3253(3) 0.44281(14) 0.0402(7) Uani 1 1 d . . . . .
H16 H 0.1567 0.2522 0.4226 0.048 Uiso 1 1 calc R U . . .
C17 C 0.1073(3) 0.6579(3) 0.42282(13) 0.0363(7) Uani 1 1 d . . . . .
C18 C 0.5746(3) 0.3898(2) 0.70071(14) 0.0333(6) Uani 1 1 d . . . . .
C19 C 0.1455(4) 0.8529(3) 0.47373(15) 0.0400(7) Uani 1 1 d . . . . .
H19 H 0.1906 0.9029 0.5082 0.048 Uiso 1 1 calc R U . . .
C20 C 0.4813(4) 0.8820(2) 0.59535(15) 0.0390(7) Uani 1 1 d . . . . .
H20 H 0.5424 0.8638 0.5571 0.047 Uiso 1 1 calc R U . . .
C21 C 0.1181(4) 0.4273(3) 0.40946(15) 0.0415(7) Uani 1 1 d . . . . .
H21 H 0.0536 0.4220 0.3681 0.050 Uiso 1 1 calc R U . . .
C22 C 0.4102(4) 1.0195(2) 0.68401(16) 0.0414(7) Uani 1 1 d . . . . .
H22 H 0.4236 1.0927 0.7056 0.050 Uiso 1 1 calc R U . . .
C23 C 0.4992(4) 0.9917(3) 0.62690(16) 0.0439(8) Uani 1 1 d . . . . .
H23 H 0.5714 1.0467 0.6095 0.053 Uiso 1 1 calc R U . . .
C24 C 0.0441(4) 0.8974(3) 0.41897(16) 0.0474(8) Uani 1 1 d . . . . .
H24 H 0.0217 0.9779 0.4170 0.057 Uiso 1 1 calc R U . . .
C25 C 0.0079(4) 0.7046(3) 0.36887(15) 0.0443(8) Uani 1 1 d . . . . .
H25 H -0.0371 0.6558 0.3339 0.053 Uiso 1 1 calc R U . . .
C26 C -0.0237(4) 0.8237(3) 0.36749(16) 0.0500(8) Uani 1 1 d . . . . .
H26 H -0.0913 0.8552 0.3316 0.060 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# 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
Cl1 C18 1.738(3) . ?
C1 C20 1.386(4) . ?
C1 C12 1.390(4) . ?
C1 C4 1.495(4) . ?
C2 C8 1.415(4) . ?
C2 C14 1.425(4) . ?
C2 C4 1.462(4) . ?
C3 C6 1.386(4) . ?
C3 C13 1.402(4) . ?
C3 C7 1.438(4) . ?
C4 C7 1.361(4) . ?
C5 C19 1.385(4) . ?
C5 C17 1.423(4) . ?
C5 C7 1.474(4) . ?
C6 C10 1.419(4) . ?
C6 C14 1.450(4) . ?
C8 C11 1.367(4) . ?
C8 H8 0.9300 . ?
C9 C18 1.369(4) . ?
C9 C14 1.400(4) . ?
C9 H9 0.9300 . ?
C10 C16 1.380(4) . ?
C10 H10 0.9300 . ?
C11 C18 1.395(4) . ?
C11 H11 0.9300 . ?
C12 C15 1.385(4) . ?
C12 H12 0.9300 . ?
C13 C21 1.380(4) . ?
C13 C17 1.466(4) . ?
C15 C22 1.382(4) . ?
C15 H15 0.9300 . ?
C16 C21 1.401(4) . ?
C16 H16 0.9300 . ?
C17 C25 1.384(4) . ?
C19 C24 1.395(4) . ?
C19 H19 0.9300 . ?
C20 C23 1.386(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 C26 1.385(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.372(5) . ?
C25 H25 0.9300 . ?
C26 H26 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
C20 C1 C12 118.7(2) . . ?
C20 C1 C4 121.8(2) . . ?
C12 C1 C4 119.5(2) . . ?
C8 C2 C14 117.7(2) . . ?
C8 C2 C4 120.0(2) . . ?
C14 C2 C4 122.2(2) . . ?
C6 C3 C13 124.3(3) . . ?
C6 C3 C7 124.8(2) . . ?
C13 C3 C7 110.8(2) . . ?
C7 C4 C2 117.9(2) . . ?
C7 C4 C1 123.0(2) . . ?
C2 C4 C1 119.1(2) . . ?
C19 C5 C17 119.7(3) . . ?
C19 C5 C7 132.4(3) . . ?
C17 C5 C7 107.8(2) . . ?
C3 C6 C10 116.0(3) . . ?
C3 C6 C14 116.7(2) . . ?
C10 C6 C14 127.3(3) . . ?
C4 C7 C3 119.6(2) . . ?
C4 C7 C5 134.2(3) . . ?
C3 C7 C5 106.0(2) . . ?
C11 C8 C2 122.4(2) . . ?
C11 C8 H8 118.8 . . ?
C2 C8 H8 118.8 . . ?
C18 C9 C14 120.7(2) . . ?
C18 C9 H9 119.6 . . ?
C14 C9 H9 119.6 . . ?
C16 C10 C6 120.2(3) . . ?
C16 C10 H10 119.9 . . ?
C6 C10 H10 119.9 . . ?
C8 C11 C18 118.5(3) . . ?
C8 C11 H11 120.7 . . ?
C18 C11 H11 120.7 . . ?
C15 C12 C1 120.6(3) . . ?
C15 C12 H12 119.7 . . ?
C1 C12 H12 119.7 . . ?
C21 C13 C3 118.5(3) . . ?
C21 C13 C17 134.6(3) . . ?
C3 C13 C17 106.9(2) . . ?
C9 C14 C2 119.0(2) . . ?
C9 C14 C6 122.3(2) . . ?
C2 C14 C6 118.7(2) . . ?
C22 C15 C12 120.1(3) . . ?
C22 C15 H15 119.9 . . ?
C12 C15 H15 119.9 . . ?
C10 C16 C21 122.4(3) . . ?
C10 C16 H16 118.8 . . ?
C21 C16 H16 118.8 . . ?
C25 C17 C5 120.2(3) . . ?
C25 C17 C13 131.2(3) . . ?
C5 C17 C13 108.5(2) . . ?
C9 C18 C11 121.5(2) . . ?
C9 C18 Cl1 120.1(2) . . ?
C11 C18 Cl1 118.3(2) . . ?
C5 C19 C24 118.8(3) . . ?
C5 C19 H19 120.6 . . ?
C24 C19 H19 120.6 . . ?
C23 C20 C1 120.7(3) . . ?
C23 C20 H20 119.7 . . ?
C1 C20 H20 119.7 . . ?
C13 C21 C16 118.6(3) . . ?
C13 C21 H21 120.7 . . ?
C16 C21 H21 120.7 . . ?
C23 C22 C15 119.7(3) . . ?
C23 C22 H22 120.1 . . ?
C15 C22 H22 120.1 . . ?
C22 C23 C20 120.2(3) . . ?
C22 C23 H23 119.9 . . ?
C20 C23 H23 119.9 . . ?
C26 C24 C19 121.1(3) . . ?
C26 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C26 C25 C17 119.5(3) . . ?
C26 C25 H25 120.3 . . ?
C17 C25 H25 120.3 . . ?
C25 C26 C24 120.7(3) . . ?
C25 C26 H26 119.6 . . ?
C24 C26 H26 119.6 . . ?

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
C8 C2 C4 C7 176.0(2) . . . . ?
C14 C2 C4 C7 -2.8(4) . . . . ?
C8 C2 C4 C1 -4.8(4) . . . . ?
C14 C2 C4 C1 176.4(2) . . . . ?
C20 C1 C4 C7 -76.2(4) . . . . ?
C12 C1 C4 C7 105.4(3) . . . . ?
C20 C1 C4 C2 104.7(3) . . . . ?
C12 C1 C4 C2 -73.7(3) . . . . ?
C13 C3 C6 C10 1.0(4) . . . . ?
C7 C3 C6 C10 177.0(2) . . . . ?
C13 C3 C6 C14 -178.7(2) . . . . ?
C7 C3 C6 C14 -2.7(4) . . . . ?
C2 C4 C7 C3 2.4(4) . . . . ?
C1 C4 C7 C3 -176.8(2) . . . . ?
C2 C4 C7 C5 178.1(3) . . . . ?
C1 C4 C7 C5 -1.1(5) . . . . ?
C6 C3 C7 C4 0.4(4) . . . . ?
C13 C3 C7 C4 176.8(2) . . . . ?
C6 C3 C7 C5 -176.4(2) . . . . ?
C13 C3 C7 C5 0.0(3) . . . . ?
C19 C5 C7 C4 0.8(5) . . . . ?
C17 C5 C7 C4 -176.1(3) . . . . ?
C19 C5 C7 C3 176.9(3) . . . . ?
C17 C5 C7 C3 0.0(3) . . . . ?
C14 C2 C8 C11 -1.2(4) . . . . ?
C4 C2 C8 C11 180.0(2) . . . . ?
C3 C6 C10 C16 -0.3(4) . . . . ?
C14 C6 C10 C16 179.3(3) . . . . ?
C2 C8 C11 C18 -0.4(4) . . . . ?
C20 C1 C12 C15 -0.7(4) . . . . ?
C4 C1 C12 C15 177.7(3) . . . . ?
C6 C3 C13 C21 -0.8(4) . . . . ?
C7 C3 C13 C21 -177.3(2) . . . . ?
C6 C3 C13 C17 176.5(2) . . . . ?
C7 C3 C13 C17 0.0(3) . . . . ?
C18 C9 C14 C2 -1.2(4) . . . . ?
C18 C9 C14 C6 179.2(2) . . . . ?
C8 C2 C14 C9 2.0(4) . . . . ?
C4 C2 C14 C9 -179.2(2) . . . . ?
C8 C2 C14 C6 -178.4(2) . . . . ?
C4 C2 C14 C6 0.4(4) . . . . ?
C3 C6 C14 C9 -178.2(2) . . . . ?
C10 C6 C14 C9 2.2(4) . . . . ?
C3 C6 C14 C2 2.2(4) . . . . ?
C10 C6 C14 C2 -177.4(3) . . . . ?
C1 C12 C15 C22 0.2(4) . . . . ?
C6 C10 C16 C21 -0.4(4) . . . . ?
C19 C5 C17 C25 0.6(4) . . . . ?
C7 C5 C17 C25 178.0(2) . . . . ?
C19 C5 C17 C13 -177.4(2) . . . . ?
C7 C5 C17 C13 0.0(3) . . . . ?
C21 C13 C17 C25 -1.0(5) . . . . ?
C3 C13 C17 C25 -177.6(3) . . . . ?
C21 C13 C17 C5 176.7(3) . . . . ?
C3 C13 C17 C5 0.0(3) . . . . ?
C14 C9 C18 C11 -0.4(4) . . . . ?
C14 C9 C18 Cl1 178.4(2) . . . . ?
C8 C11 C18 C9 1.2(4) . . . . ?
C8 C11 C18 Cl1 -177.6(2) . . . . ?
C17 C5 C19 C24 -0.2(4) . . . . ?
C7 C5 C19 C24 -176.8(3) . . . . ?
C12 C1 C20 C23 0.5(4) . . . . ?
C4 C1 C20 C23 -178.0(3) . . . . ?
C3 C13 C21 C16 0.0(4) . . . . ?
C17 C13 C21 C16 -176.3(3) . . . . ?
C10 C16 C21 C13 0.6(4) . . . . ?
C12 C15 C22 C23 0.7(5) . . . . ?
C15 C22 C23 C20 -1.0(5) . . . . ?
C1 C20 C23 C22 0.4(5) . . . . ?
C5 C19 C24 C26 0.0(4) . . . . ?
C5 C17 C25 C26 -0.8(4) . . . . ?
C13 C17 C25 C26 176.6(3) . . . . ?
C17 C25 C26 C24 0.7(4) . . . . ?
C19 C24 C26 C25 -0.3(5) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_20191223takano_enyne_iPr
_database_code_depnum_ccdc_archive 'CCDC 1990131'
loop_
_audit_author_name
_audit_author_address
'Hideaki Takano'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H17 Cl'
_chemical_formula_moiety         'C23 H17 Cl'
_chemical_formula_weight         328.84
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.5655(2)
_cell_length_b                   10.9027(3)
_cell_length_c                   11.0880(3)
_cell_angle_alpha                113.594(8)
_cell_angle_beta                 103.447(7)
_cell_angle_gamma                93.898(7)
_cell_volume                     801.74(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8765
_cell_measurement_theta_min      4.50
_cell_measurement_theta_max      68.22
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       unknown
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344.00
_exptl_absorpt_coefficient_mu    2.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.333
_exptl_absorpt_correction_T_max  0.660

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9006
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_theta_max         68.226
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_limit_h_min       9999
_diffrn_reflns_limit_h_max       -9999
_diffrn_reflns_limit_k_min       9999
_diffrn_reflns_limit_k_max       -9999
_diffrn_reflns_limit_l_min       9999
_diffrn_reflns_limit_l_max       -9999
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2855
_reflns_number_gt                2580
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1279
_refine_ls_wR_factor_gt          0.1253
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2855
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.113
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0603P)²+0.3581P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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
Cl1 Cl 0.24297(7) 0.58611(5) 0.13555(5) 0.03289(19) Uani 1 1 d . . . . .
C1 C 0.3990(3) 0.67194(18) 0.67334(19) 0.0223(4) Uani 1 1 d . . . . .
C2 C 0.2532(3) 0.46605(18) 0.6644(2) 0.0230(4) Uani 1 1 d . . . . .
C3 C 0.4950(3) 0.80349(18) 0.68042(19) 0.0231(4) Uani 1 1 d . . . . .
C4 C 0.2946(3) 0.54280(18) 0.59116(19) 0.0220(4) Uani 1 1 d . . . . .
C5 C 0.2656(3) 0.55458(19) 0.36741(19) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.3361 0.6418 0.4127 0.029 Uiso 1 1 calc R U . . .
C6 C 0.4620(3) 0.72429(19) 0.8170(2) 0.0249(4) Uani 1 1 d . . . . .
C7 C 0.1211(3) 0.35159(19) 0.3717(2) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.3202(3) 0.5219(2) 0.8081(2) 0.0262(4) Uani 1 1 d . . . . .
H8 H 0.2927 0.4694 0.8522 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5582(3) 0.85477(19) 0.8256(2) 0.0246(4) Uani 1 1 d . . . . .
C10 C 0.5399(3) 0.87704(19) 0.6135(2) 0.0274(4) Uani 1 1 d . . . . .
H10 H 0.4998 0.8438 0.5184 0.033 Uiso 1 1 calc R U . . .
C11 C 0.0781(3) 0.28002(19) 0.4484(2) 0.0270(4) Uani 1 1 d . . . . .
H11 H 0.0042 0.1941 0.4004 0.032 Uiso 1 1 calc R U . . .
C12 C 0.1396(3) 0.33110(19) 0.5866(2) 0.0249(4) Uani 1 1 d . . . . .
C13 C 0.1983(3) 0.4950(2) 0.2271(2) 0.0262(4) Uani 1 1 d . . . . .
C14 C 0.2281(3) 0.48375(18) 0.44254(19) 0.0227(4) Uani 1 1 d . . . . .
C15 C 0.7117(3) 1.0558(2) 0.8376(2) 0.0320(5) Uani 1 1 d . . . . .
H15 H 0.7849 1.1418 0.8885 0.038 Uiso 1 1 calc R U . . .
C16 C 0.0951(3) 0.3641(2) 0.1554(2) 0.0301(5) Uani 1 1 d . . . . .
H16 H 0.0526 0.3248 0.0601 0.036 Uiso 1 1 calc R U . . .
C17 C 0.6660(3) 0.9792(2) 0.9071(2) 0.0296(5) Uani 1 1 d . . . . .
H17 H 0.7071 1.0118 1.0020 0.035 Uiso 1 1 calc R U . . .
C18 C 0.2428(3) 0.1705(2) 0.6922(2) 0.0291(5) Uani 1 1 d . . . . .
H18A H 0.2545 0.1011 0.6075 0.035 Uiso 1 1 calc R U . . .
H18B H 0.3596 0.2336 0.7388 0.035 Uiso 1 1 calc R U . . .
C19 C 0.0909(3) 0.24692(19) 0.6582(2) 0.0280(5) Uani 1 1 d . . . . .
H19A H -0.0215 0.1816 0.6001 0.034 Uiso 1 1 calc R U . . .
H19B H 0.0663 0.3062 0.7426 0.034 Uiso 1 1 calc R U . . .
C20 C 0.0569(3) 0.2937(2) 0.2276(2) 0.0303(5) Uani 1 1 d . . . . .
H20 H -0.0126 0.2062 0.1804 0.036 Uiso 1 1 calc R U . . .
C21 C 0.6511(3) 1.0069(2) 0.6979(2) 0.0310(5) Uani 1 1 d . . . . .
H21 H 0.6842 1.0610 0.6568 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4253(3) 0.6514(2) 0.8878(2) 0.0278(4) Uani 1 1 d . . . . .
H22 H 0.4682 0.6866 0.9829 0.033 Uiso 1 1 calc R U . . .
C23 C 0.2034(3) 0.1038(2) 0.7824(2) 0.0329(5) Uani 1 1 d . . . . .
H23A H 0.3019 0.0571 0.8011 0.039 Uiso 1 1 calc R U . . .
H23B H 0.1941 0.1722 0.8672 0.039 Uiso 1 1 calc R U . . .
H23C H 0.0891 0.0398 0.7359 0.039 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# 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
Cl1 C13 1.747(2) . ?
C1 C4 1.387(3) . ?
C1 C6 1.405(3) . ?
C1 C3 1.527(3) . ?
C2 C8 1.404(3) . ?
C2 C4 1.444(2) . ?
C2 C12 1.454(3) . ?
C3 C10 1.366(3) . ?
C3 C9 1.420(3) . ?
C4 C14 1.451(3) . ?
C5 C13 1.371(3) . ?
C5 C14 1.402(3) . ?
C5 H5 0.9300 . ?
C6 C22 1.377(3) . ?
C6 C9 1.511(3) . ?
C7 C20 1.407(3) . ?
C7 C14 1.410(3) . ?
C7 C11 1.436(3) . ?
C8 C22 1.388(3) . ?
C8 H8 0.9300 . ?
C9 C17 1.359(3) . ?
C10 C21 1.414(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.352(3) . ?
C11 H11 0.9300 . ?
C12 C19 1.510(2) . ?
C13 C16 1.389(3) . ?
C15 C21 1.367(3) . ?
C15 C17 1.418(3) . ?
C15 H15 0.9300 . ?
C16 C20 1.372(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.520(3) . ?
C18 C19 1.529(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C4 C1 C6 122.81(17) . . ?
C4 C1 C3 147.30(18) . . ?
C6 C1 C3 89.88(15) . . ?
C8 C2 C4 120.32(17) . . ?
C8 C2 C12 120.96(17) . . ?
C4 C2 C12 118.71(17) . . ?
C10 C3 C9 121.64(17) . . ?
C10 C3 C1 148.88(18) . . ?
C9 C3 C1 89.45(15) . . ?
C1 C4 C2 114.98(17) . . ?
C1 C4 C14 124.86(17) . . ?
C2 C4 C14 120.16(16) . . ?
C13 C5 C14 119.87(18) . . ?
C13 C5 H5 120.1 . . ?
C14 C5 H5 120.1 . . ?
C22 C6 C1 122.67(18) . . ?
C22 C6 C9 146.59(18) . . ?
C1 C6 C9 90.71(15) . . ?
C20 C7 C14 119.14(18) . . ?
C20 C7 C11 121.55(18) . . ?
C14 C7 C11 119.30(17) . . ?
C22 C8 C2 123.45(17) . . ?
C22 C8 H8 118.3 . . ?
C2 C8 H8 118.3 . . ?
C17 C9 C3 122.80(18) . . ?
C17 C9 C6 147.22(18) . . ?
C3 C9 C6 89.96(15) . . ?
C3 C10 C21 115.78(18) . . ?
C3 C10 H10 122.1 . . ?
C21 C10 H10 122.1 . . ?
C12 C11 C7 123.37(17) . . ?
C12 C11 H11 118.3 . . ?
C7 C11 H11 118.3 . . ?
C11 C12 C2 119.48(17) . . ?
C11 C12 C19 119.62(17) . . ?
C2 C12 C19 120.89(17) . . ?
C5 C13 C16 121.85(18) . . ?
C5 C13 Cl1 119.17(15) . . ?
C16 C13 Cl1 118.98(15) . . ?
C5 C14 C7 119.07(17) . . ?
C5 C14 C4 121.99(17) . . ?
C7 C14 C4 118.93(17) . . ?
C21 C15 C17 121.85(18) . . ?
C21 C15 H15 119.1 . . ?
C17 C15 H15 119.1 . . ?
C20 C16 C13 118.93(18) . . ?
C20 C16 H16 120.5 . . ?
C13 C16 H16 120.5 . . ?
C9 C17 C15 115.54(18) . . ?
C9 C17 H17 122.2 . . ?
C15 C17 H17 122.2 . . ?
C23 C18 C19 112.29(17) . . ?
C23 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
C23 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.9 . . ?
C12 C19 C18 113.31(16) . . ?
C12 C19 H19A 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C12 C19 H19B 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C16 C20 C7 121.12(18) . . ?
C16 C20 H20 119.4 . . ?
C7 C20 H20 119.4 . . ?
C15 C21 C10 122.38(18) . . ?
C15 C21 H21 118.8 . . ?
C10 C21 H21 118.8 . . ?
C6 C22 C8 115.75(18) . . ?
C6 C22 H22 122.1 . . ?
C8 C22 H22 122.1 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C4 C1 C3 C10 -0.5(6) . . . . ?
C6 C1 C3 C10 177.9(3) . . . . ?
C4 C1 C3 C9 -178.2(3) . . . . ?
C6 C1 C3 C9 0.21(16) . . . . ?
C6 C1 C4 C2 0.6(3) . . . . ?
C3 C1 C4 C2 178.8(3) . . . . ?
C6 C1 C4 C14 -179.31(17) . . . . ?
C3 C1 C4 C14 -1.2(4) . . . . ?
C8 C2 C4 C1 -1.1(3) . . . . ?
C12 C2 C4 C1 178.19(17) . . . . ?
C8 C2 C4 C14 178.82(17) . . . . ?
C12 C2 C4 C14 -1.9(3) . . . . ?
C4 C1 C6 C22 0.1(3) . . . . ?
C3 C1 C6 C22 -178.85(19) . . . . ?
C4 C1 C6 C9 178.79(19) . . . . ?
C3 C1 C6 C9 -0.20(15) . . . . ?
C4 C2 C8 C22 0.9(3) . . . . ?
C12 C2 C8 C22 -178.38(18) . . . . ?
C10 C3 C9 C17 0.2(3) . . . . ?
C1 C3 C9 C17 178.8(2) . . . . ?
C10 C3 C9 C6 -178.82(18) . . . . ?
C1 C3 C9 C6 -0.19(14) . . . . ?
C22 C6 C9 C17 -0.3(6) . . . . ?
C1 C6 C9 C17 -178.2(3) . . . . ?
C22 C6 C9 C3 178.2(3) . . . . ?
C1 C6 C9 C3 0.21(16) . . . . ?
C9 C3 C10 C21 -0.5(3) . . . . ?
C1 C3 C10 C21 -177.9(3) . . . . ?
C20 C7 C11 C12 178.84(19) . . . . ?
C14 C7 C11 C12 -2.0(3) . . . . ?
C7 C11 C12 C2 0.9(3) . . . . ?
C7 C11 C12 C19 -178.58(17) . . . . ?
C8 C2 C12 C11 -179.67(18) . . . . ?
C4 C2 C12 C11 1.0(3) . . . . ?
C8 C2 C12 C19 -0.2(3) . . . . ?
C4 C2 C12 C19 -179.50(16) . . . . ?
C14 C5 C13 C16 -1.1(3) . . . . ?
C14 C5 C13 Cl1 178.83(14) . . . . ?
C13 C5 C14 C7 0.0(3) . . . . ?
C13 C5 C14 C4 -179.36(18) . . . . ?
C20 C7 C14 C5 0.8(3) . . . . ?
C11 C7 C14 C5 -178.36(16) . . . . ?
C20 C7 C14 C4 -179.76(17) . . . . ?
C11 C7 C14 C4 1.1(3) . . . . ?
C1 C4 C14 C5 0.2(3) . . . . ?
C2 C4 C14 C5 -179.78(17) . . . . ?
C1 C4 C14 C7 -179.24(18) . . . . ?
C2 C4 C14 C7 0.8(3) . . . . ?
C5 C13 C16 C20 1.2(3) . . . . ?
Cl1 C13 C16 C20 -178.70(15) . . . . ?
C3 C9 C17 C15 0.2(3) . . . . ?
C6 C9 C17 C15 178.3(3) . . . . ?
C21 C15 C17 C9 -0.2(3) . . . . ?
C11 C12 C19 C18 97.1(2) . . . . ?
C2 C12 C19 C18 -82.4(2) . . . . ?
C23 C18 C19 C12 171.48(17) . . . . ?
C13 C16 C20 C7 -0.3(3) . . . . ?
C14 C7 C20 C16 -0.7(3) . . . . ?
C11 C7 C20 C16 178.47(18) . . . . ?
C17 C15 C21 C10 -0.2(3) . . . . ?
C3 C10 C21 C15 0.6(3) . . . . ?
C1 C6 C22 C8 -0.4(3) . . . . ?
C9 C6 C22 C8 -178.0(3) . . . . ?
C2 C8 C22 C6 -0.1(3) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


####################################################################### 
# 
# 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_20191203_propyl_TM-A
_database_code_depnum_ccdc_archive 'CCDC 1990130'
loop_
_audit_author_name
_audit_author_address
'Hideaki Takano'
;Waseda Uniniversity
Japan
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-07-09 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C23 H17 Cl'
_chemical_formula_moiety         'C23 H17 Cl'
_chemical_formula_weight         328.84
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
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                   19.2706(14)
_cell_length_b                   4.9741(4)
_cell_length_c                   33.688(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 102.847(7)
_cell_angle_gamma                90.0000
_cell_volume                     3148.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6084
_cell_measurement_theta_min      4.60
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376.00
_exptl_absorpt_coefficient_mu    2.114
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_T_max  0.919

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8088
_diffrn_reflns_av_R_equivalents  0.1218
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_min         4.707
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measured_fraction_theta_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2695
_reflns_number_gt                1546
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1933
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_ref         0.1586
_refine_ls_wR_factor_gt          0.1320
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2695
_refine_ls_number_parameters     217
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+2.6954P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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
Cl1 Cl 0.41947(5) -0.23507(18) 0.29042(3) 0.0440(4) Uani 1 1 d . . . . .
C1 C 0.67150(18) 0.6051(7) 0.34950(10) 0.0273(9) Uani 1 1 d . . . . .
C2 C 0.76206(19) 0.6534(7) 0.31161(10) 0.0307(9) Uani 1 1 d . . . . .
H2 H 0.8038 0.7362 0.3068 0.037 Uiso 1 1 calc R U . . .
C3 C 0.63589(18) 0.4067(7) 0.32422(10) 0.0301(9) Uani 1 1 d . . . . .
C4 C 0.48741(19) 0.3012(7) 0.37784(11) 0.0345(10) Uani 1 1 d . . . . .
H4 H 0.4723 0.3655 0.4011 0.041 Uiso 1 1 calc R U . . .
C5 C 0.75469(19) 0.9274(7) 0.37656(10) 0.0290(9) Uani 1 1 d . . . . .
C6 C 0.73395(18) 0.7307(7) 0.34395(11) 0.0281(9) Uani 1 1 d . . . . .
C7 C 0.66628(19) 0.3281(7) 0.29152(10) 0.0329(10) Uani 1 1 d . . . . .
H7 H 0.6444 0.1911 0.2733 0.039 Uiso 1 1 calc R U . . .
C8 C 0.44799(18) 0.1082(7) 0.35458(11) 0.0331(9) Uani 1 1 d . . . . .
H8 H 0.4058 0.0419 0.3613 0.040 Uiso 1 1 calc R U . . .
C9 C 0.71504(19) 1.0860(7) 0.43570(10) 0.0321(9) Uani 1 1 d . . . . .
H9 H 0.6833 1.0803 0.4536 0.039 Uiso 1 1 calc R U . . .
C10 C 0.47035(19) 0.0083(7) 0.32064(10) 0.0328(10) Uani 1 1 d . . . . .
C11 C 0.54997(19) 0.4104(7) 0.36883(11) 0.0323(9) Uani 1 1 d . . . . .
C12 C 0.81914(19) 1.2734(7) 0.41769(11) 0.0345(10) Uani 1 1 d . . . . .
H12 H 0.8576 1.3973 0.4232 0.041 Uiso 1 1 calc R U . . .
C13 C 0.70467(18) 0.9161(7) 0.40220(10) 0.0280(9) Uani 1 1 d . . . . .
C14 C 0.53098(18) 0.1040(7) 0.31071(10) 0.0331(10) Uani 1 1 d . . . . .
H14 H 0.5453 0.0347 0.2875 0.040 Uiso 1 1 calc R U . . .
C15 C 0.7276(2) 0.4502(7) 0.28603(10) 0.0353(10) Uani 1 1 d . . . . .
H15 H 0.7473 0.3939 0.2639 0.042 Uiso 1 1 calc R U . . .
C16 C 0.56568(18) 0.7365(7) 0.43097(10) 0.0327(10) Uani 1 1 d . . . . .
H16A H 0.5769 0.9309 0.4331 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5134 0.7175 0.4264 0.039 Uiso 1 1 calc R U . . .
C17 C 0.59982(18) 0.6020(7) 0.47108(10) 0.0356(10) Uani 1 1 d . . . . .
H17A H 0.6522 0.6085 0.4749 0.043 Uiso 1 1 calc R U . . .
H17B H 0.5853 0.4108 0.4701 0.043 Uiso 1 1 calc R U . . .
C18 C 0.58981(19) 0.6223(7) 0.39436(11) 0.0330(9) Uani 1 1 d . . . . .
C19 C 0.81093(19) 1.1040(7) 0.38439(10) 0.0321(9) Uani 1 1 d . . . . .
H19 H 0.8438 1.1096 0.3672 0.039 Uiso 1 1 calc R U . . .
C20 C 0.6502(2) 0.7129(7) 0.38473(10) 0.0318(10) Uani 1 1 d . . . . .
C21 C 0.5786(2) 0.7374(7) 0.50696(10) 0.0427(11) Uani 1 1 d . . . . .
H21A H 0.6016 0.6453 0.5322 0.051 Uiso 1 1 calc R U . . .
H21B H 0.5937 0.9260 0.5084 0.051 Uiso 1 1 calc R U . . .
H21C H 0.5268 0.7284 0.5035 0.051 Uiso 1 1 calc R U . . .
C22 C 0.7715(2) 1.2630(7) 0.44300(11) 0.0338(10) Uani 1 1 d . . . . .
H22 H 0.7778 1.3801 0.4658 0.041 Uiso 1 1 calc R U . . .
C23 C 0.57187(19) 0.3015(7) 0.33424(11) 0.0283(9) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# 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
Cl1 C10 1.737(3) . ?
C1 C3 1.382(4) . ?
C1 C6 1.405(4) . ?
C1 C20 1.442(4) . ?
C2 C6 1.375(4) . ?
C2 C15 1.396(4) . ?
C2 H2 0.9500 . ?
C3 C7 1.413(4) . ?
C3 C23 1.447(5) . ?
C4 C8 1.360(4) . ?
C4 C11 1.415(5) . ?
C4 H4 0.9500 . ?
C5 C19 1.374(4) . ?
C5 C13 1.431(4) . ?
C5 C6 1.459(5) . ?
C7 C15 1.377(5) . ?
C7 H7 0.9500 . ?
C8 C10 1.399(4) . ?
C8 H8 0.9500 . ?
C9 C22 1.378(4) . ?
C9 C13 1.388(4) . ?
C9 H9 0.9500 . ?
C10 C14 1.370(4) . ?
C11 C23 1.431(5) . ?
C11 C18 1.465(5) . ?
C12 C22 1.386(5) . ?
C12 C19 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C20 1.481(5) . ?
C14 C23 1.391(4) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 C17 1.520(4) . ?
C16 C18 1.522(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C21 1.517(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.354(4) . ?
C19 H19 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22 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
C3 C1 C6 123.9(3) . . ?
C3 C1 C20 125.4(3) . . ?
C6 C1 C20 110.6(3) . . ?
C6 C2 C15 118.3(3) . . ?
C6 C2 H2 120.8 . . ?
C15 C2 H2 120.8 . . ?
C1 C3 C7 116.3(3) . . ?
C1 C3 C23 116.5(3) . . ?
C7 C3 C23 127.2(3) . . ?
C8 C4 C11 122.7(4) . . ?
C8 C4 H4 118.6 . . ?
C11 C4 H4 118.6 . . ?
C19 C5 C13 121.2(3) . . ?
C19 C5 C6 130.2(3) . . ?
C13 C5 C6 108.6(3) . . ?
C2 C6 C1 118.8(3) . . ?
C2 C6 C5 133.9(3) . . ?
C1 C6 C5 107.3(3) . . ?
C15 C7 C3 120.0(3) . . ?
C15 C7 H7 120.0 . . ?
C3 C7 H7 120.0 . . ?
C4 C8 C10 119.2(3) . . ?
C4 C8 H8 120.4 . . ?
C10 C8 H8 120.4 . . ?
C22 C9 C13 119.9(3) . . ?
C22 C9 H9 120.0 . . ?
C13 C9 H9 120.0 . . ?
C14 C10 C8 120.7(3) . . ?
C14 C10 Cl1 120.0(3) . . ?
C8 C10 Cl1 119.3(3) . . ?
C4 C11 C23 116.7(3) . . ?
C4 C11 C18 120.7(3) . . ?
C23 C11 C18 122.6(3) . . ?
C22 C12 C19 120.2(3) . . ?
C22 C12 H12 119.9 . . ?
C19 C12 H12 119.9 . . ?
C9 C13 C5 118.2(3) . . ?
C9 C13 C20 134.4(3) . . ?
C5 C13 C20 107.4(3) . . ?
C10 C14 C23 120.8(3) . . ?
C10 C14 H14 119.6 . . ?
C23 C14 H14 119.6 . . ?
C7 C15 C2 122.7(3) . . ?
C7 C15 H15 118.6 . . ?
C2 C15 H15 118.6 . . ?
C17 C16 C18 114.0(3) . . ?
C17 C16 H16A 108.8 . . ?
C18 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C18 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 C21 111.9(3) . . ?
C16 C17 H17A 109.2 . . ?
C21 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C21 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C20 C18 C11 117.7(3) . . ?
C20 C18 C16 120.3(3) . . ?
C11 C18 C16 122.0(3) . . ?
C5 C19 C12 119.2(3) . . ?
C5 C19 H19 120.4 . . ?
C12 C19 H19 120.4 . . ?
C18 C20 C1 119.4(3) . . ?
C18 C20 C13 134.7(3) . . ?
C1 C20 C13 106.0(3) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C9 C22 C12 121.3(3) . . ?
C9 C22 H22 119.4 . . ?
C12 C22 H22 119.4 . . ?
C14 C23 C11 119.9(3) . . ?
C14 C23 C3 121.8(3) . . ?
C11 C23 C3 118.3(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
C6 C1 C3 C7 1.0(5) . . . . ?
C20 C1 C3 C7 -179.4(3) . . . . ?
C6 C1 C3 C23 -179.3(3) . . . . ?
C20 C1 C3 C23 0.3(5) . . . . ?
C15 C2 C6 C1 -0.9(5) . . . . ?
C15 C2 C6 C5 179.2(3) . . . . ?
C3 C1 C6 C2 -0.1(5) . . . . ?
C20 C1 C6 C2 -179.8(3) . . . . ?
C3 C1 C6 C5 179.8(3) . . . . ?
C20 C1 C6 C5 0.1(4) . . . . ?
C19 C5 C6 C2 1.0(6) . . . . ?
C13 C5 C6 C2 -179.2(3) . . . . ?
C19 C5 C6 C1 -178.9(3) . . . . ?
C13 C5 C6 C1 0.9(4) . . . . ?
C1 C3 C7 C15 -0.7(5) . . . . ?
C23 C3 C7 C15 179.6(3) . . . . ?
C11 C4 C8 C10 1.2(5) . . . . ?
C4 C8 C10 C14 -0.3(5) . . . . ?
C4 C8 C10 Cl1 -179.1(3) . . . . ?
C8 C4 C11 C23 -1.9(5) . . . . ?
C8 C4 C11 C18 178.7(3) . . . . ?
C22 C9 C13 C5 1.3(5) . . . . ?
C22 C9 C13 C20 -177.7(3) . . . . ?
C19 C5 C13 C9 -1.0(5) . . . . ?
C6 C5 C13 C9 179.2(3) . . . . ?
C19 C5 C13 C20 178.4(3) . . . . ?
C6 C5 C13 C20 -1.5(4) . . . . ?
C8 C10 C14 C23 0.4(5) . . . . ?
Cl1 C10 C14 C23 179.1(2) . . . . ?
C3 C7 C15 C2 -0.3(5) . . . . ?
C6 C2 C15 C7 1.1(5) . . . . ?
C18 C16 C17 C21 175.4(3) . . . . ?
C4 C11 C18 C20 178.2(3) . . . . ?
C23 C11 C18 C20 -1.1(5) . . . . ?
C4 C11 C18 C16 -0.8(5) . . . . ?
C23 C11 C18 C16 179.8(3) . . . . ?
C17 C16 C18 C20 -84.8(4) . . . . ?
C17 C16 C18 C11 94.2(4) . . . . ?
C13 C5 C19 C12 0.0(5) . . . . ?
C6 C5 C19 C12 179.8(3) . . . . ?
C22 C12 C19 C5 0.6(5) . . . . ?
C11 C18 C20 C1 2.0(5) . . . . ?
C16 C18 C20 C1 -179.0(3) . . . . ?
C11 C18 C20 C13 -179.4(3) . . . . ?
C16 C18 C20 C13 -0.3(6) . . . . ?
C3 C1 C20 C18 -1.7(5) . . . . ?
C6 C1 C20 C18 178.0(3) . . . . ?
C3 C1 C20 C13 179.3(3) . . . . ?
C6 C1 C20 C13 -1.0(4) . . . . ?
C9 C13 C20 C18 1.9(7) . . . . ?
C5 C13 C20 C18 -177.3(4) . . . . ?
C9 C13 C20 C1 -179.4(4) . . . . ?
C5 C13 C20 C1 1.5(4) . . . . ?
C13 C9 C22 C12 -0.8(5) . . . . ?
C19 C12 C22 C9 -0.2(5) . . . . ?
C10 C14 C23 C11 -1.2(5) . . . . ?
C10 C14 C23 C3 -179.7(3) . . . . ?
C4 C11 C23 C14 1.9(5) . . . . ?
C18 C11 C23 C14 -178.7(3) . . . . ?
C4 C11 C23 C3 -179.6(3) . . . . ?
C18 C11 C23 C3 -0.2(5) . . . . ?
C1 C3 C23 C14 179.1(3) . . . . ?
C7 C3 C23 C14 -1.3(5) . . . . ?
C1 C3 C23 C11 0.6(5) . . . . ?
C7 C3 C23 C11 -179.8(3) . . . . ?

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

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6


